data_ABC-1
_audit_creation_date               2026-02-27
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C8 H5 N O5 P, C3 H5 N2'
_chemical_formula_sum              'C11 H10 N3 O5 P'
_chemical_formula_weight           295.19
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     9.0258(3)
_cell_length_b                     9.8458(3)
_cell_length_c                     13.6802(4)
_cell_angle_alpha                  90
_cell_angle_beta                   94.5840(10)
_cell_angle_gamma                  90
_cell_volume                       1211.82(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9306
_cell_measurement_temperature      294.00
_cell_measurement_theta_max        28.21
_cell_measurement_theta_min        2.81
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.252
_exptl_absorpt_correction_T_max    0.6849
_exptl_absorpt_correction_T_min    0.5817
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0937 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.8493.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.618
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               608
_exptl_crystal_size_max            0.2
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0712
_diffrn_reflns_av_unetI/netI       0.0392
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              22860
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.330
_diffrn_reflns_theta_min           2.552
_diffrn_ambient_temperature        294.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             30.0
_diffrn_source_power               1.5
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2411
_reflns_number_total               3005
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.316
_refine_diff_density_min           -0.370
_refine_diff_density_rms           0.070
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.116
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       182
_refine_ls_number_reflns           3005
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0711
_refine_ls_R_factor_gt             0.0505
_refine_ls_restrained_S_all        1.116
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0406P)²+1.3526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1111
_refine_ls_wR_factor_ref           0.1291
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3B), N2(H2), C3(H3A), C4(H4), C11(H11), C7(H7), C6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.29790(7) 0.93825(5) 0.23204(4) 0.02374(16) Uani 1 1 d . . . . .
 O1 O 0.20910(18) 0.81269(15) 0.25100(12) 0.0311(4) Uani 1 1 d . . . . .
 O5 O 0.3314(2) 0.96446(17) 0.12852(12) 0.0349(4) Uani 1 1 d . . . . .
 O3 O 0.2111(2) 1.06026(16) 0.27478(13) 0.0347(4) Uani 1 1 d . . . . .
 H3 H 0.253100 1.131716 0.263440 0.052 Uiso 1 1 calc R U . . .
 O2 O 0.6321(2) 0.7062(2) 0.25337(14) 0.0476(5) Uani 1 1 d . . . . .
 O4 O 0.3506(2) 0.9017(2) 0.47481(15) 0.0499(5) Uani 1 1 d . . . . .
 N1 N 0.4923(2) 0.8042(2) 0.36499(15) 0.0312(5) Uani 1 1 d . . . . .
 N3 N 0.3940(2) 0.7723(2) 0.00013(16) 0.0359(5) Uani 1 1 d . . . . .
 H3B H 0.371598 0.830733 0.043287 0.043 Uiso 1 1 calc R U . . .
 N2 N 0.4964(2) 0.6798(2) -0.11856(16) 0.0389(5) Uani 1 1 d . . . . .
 H2 H 0.552105 0.667476 -0.165930 0.047 Uiso 1 1 calc R U . . .
 C9 C 0.4993(2) 0.5615(2) 0.47321(15) 0.0253(5) Uani 1 1 d . . . . .
 C1 C 0.4236(2) 0.4310(2) 0.61212(16) 0.0274(5) Uani 1 1 d . . . . .
 C2 C 0.4208(3) 0.6737(2) 0.50634(16) 0.0285(5) Uani 1 1 d . . . . .
 C3 C 0.3471(3) 0.5424(3) 0.64262(17) 0.0351(6) Uani 1 1 d . . . . .
 H3A H 0.296157 0.536567 0.698923 0.042 Uiso 1 1 calc R U . . .
 C4 C 0.3454(3) 0.6641(3) 0.58974(18) 0.0357(6) Uani 1 1 d . . . . .
 H4 H 0.293249 0.738631 0.610900 0.043 Uiso 1 1 calc R U . . .
 C10 C 0.4170(3) 0.8016(3) 0.45021(18) 0.0322(5) Uani 1 1 d . . . . .
 C5 C 0.5710(3) 0.6957(3) 0.32919(17) 0.0314(5) Uani 1 1 d . . . . .
 C8 C 0.4764(3) 0.9285(3) 0.3059(2) 0.0361(6) Uani 1 1 d . . . . .
 H8A H 0.556373 0.932589 0.262698 0.043 Uiso 1 1 calc R U . . .
 H8B H 0.485871 1.006639 0.349179 0.043 Uiso 1 1 calc R U . . .
 C11 C 0.3337(3) 0.6453(3) -0.01203(19) 0.0373(6) Uani 1 1 d . . . . .
 H11 H 0.261966 0.606581 0.024427 0.045 Uiso 1 1 calc R U . . .
 C7 C 0.3981(3) 0.5875(3) -0.0868(2) 0.0404(6) Uani 1 1 d . . . . .
 H7 H 0.379240 0.500977 -0.112073 0.049 Uiso 1 1 calc R U . . .
 C6 C 0.4921(3) 0.7905(3) -0.0651(2) 0.0396(6) Uani 1 1 d . . . . .
 H6 H 0.548679 0.868297 -0.072072 0.048 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O1 1.5070(16) . ?
 P1 O5 1.4941(16) . ?
 P1 O3 1.5724(16) . ?
 P1 C8 1.835(3) . ?
 O3 H3 0.8200 . ?
 O2 C5 1.217(3) . ?
 O4 C10 1.215(3) . ?
 N1 C10 1.396(3) . ?
 N1 C5 1.394(3) . ?
 N1 C8 1.467(3) . ?
 N3 H3B 0.8600 . ?
 N3 C11 1.369(3) . ?
 N3 C6 1.318(3) . ?
 N2 H2 0.8600 . ?
 N2 C7 1.365(3) . ?
 N2 C6 1.315(3) . ?
 C9 C9 1.416(4) 3_666 ?
 C9 C1 1.408(3) 3_666 ?
 C9 C2 1.406(3) . ?
 C1 C3 1.378(3) . ?
 C1 C5 1.482(3) 3_666 ?
 C2 C4 1.378(3) . ?
 C2 C10 1.474(3) . ?
 C3 H3A 0.9300 . ?
 C3 C4 1.400(4) . ?
 C4 H4 0.9300 . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C11 H11 0.9300 . ?
 C11 C7 1.342(4) . ?
 C7 H7 0.9300 . ?
 C6 H6 0.9300 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 O3 105.96(9) . . ?
 O1 P1 C8 108.55(10) . . ?
 O5 P1 O1 117.10(10) . . ?
 O5 P1 O3 111.41(10) . . ?
 O5 P1 C8 107.21(11) . . ?
 O3 P1 C8 106.07(12) . . ?
 P1 O3 H3 109.5 . . ?
 C10 N1 C8 116.3(2) . . ?
 C5 N1 C10 125.1(2) . . ?
 C5 N1 C8 118.4(2) . . ?
 C11 N3 H3B 125.6 . . ?
 C6 N3 H3B 125.6 . . ?
 C6 N3 C11 108.9(2) . . ?
 C7 N2 H2 125.5 . . ?
 C6 N2 H2 125.5 . . ?
 C6 N2 C7 109.0(2) . . ?
 C1 C9 C9 119.3(2) 3_666 3_666 ?
 C2 C9 C9 119.3(2) . 3_666 ?
 C2 C9 C1 121.4(2) . 3_666 ?
 C9 C1 C5 119.7(2) 3_666 3_666 ?
 C3 C1 C9 120.2(2) . 3_666 ?
 C3 C1 C5 120.1(2) . 3_666 ?
 C9 C2 C10 119.6(2) . . ?
 C4 C2 C9 120.6(2) . . ?
 C4 C2 C10 119.8(2) . . ?
 C1 C3 H3A 119.7 . . ?
 C1 C3 C4 120.7(2) . . ?
 C4 C3 H3A 119.7 . . ?
 C2 C4 C3 120.0(2) . . ?
 C2 C4 H4 120.0 . . ?
 C3 C4 H4 120.0 . . ?
 O4 C10 N1 120.0(2) . . ?
 O4 C10 C2 122.7(2) . . ?
 N1 C10 C2 117.3(2) . . ?
 O2 C5 N1 120.9(2) . . ?
 O2 C5 C1 122.4(2) . 3_666 ?
 N1 C5 C1 116.8(2) . 3_666 ?
 P1 C8 H8A 109.0 . . ?
 P1 C8 H8B 109.0 . . ?
 N1 C8 P1 112.95(17) . . ?
 N1 C8 H8A 109.0 . . ?
 N1 C8 H8B 109.0 . . ?
 H8A C8 H8B 107.8 . . ?
 N3 C11 H11 126.6 . . ?
 C7 C11 N3 106.7(2) . . ?
 C7 C11 H11 126.6 . . ?
 N2 C7 H7 126.5 . . ?
 C11 C7 N2 107.0(2) . . ?
 C11 C7 H7 126.5 . . ?
 N3 C6 H6 125.8 . . ?
 N2 C6 N3 108.4(2) . . ?
 N2 C6 H6 125.8 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O1 P1 C8 N1 0.1(2) . . . . ?
 O5 P1 C8 N1 -127.26(18) . . . . ?
 O3 P1 C8 N1 113.60(19) . . . . ?
 N3 C11 C7 N2 0.1(3) . . . . ?
 C9 C9 C2 C4 -0.3(4) 3_666 . . . ?
 C9 C9 C2 C10 -179.1(3) 3_666 . . . ?
 C9 C1 C3 C4 -0.2(4) 3_666 . . . ?
 C9 C2 C4 C3 0.4(4) . . . . ?
 C9 C2 C10 O4 179.7(2) . . . . ?
 C9 C2 C10 N1 0.4(3) . . . . ?
 C1 C9 C2 C4 179.7(2) 3_666 . . . ?
 C1 C9 C2 C10 0.8(4) 3_666 . . . ?
 C1 C3 C4 C2 -0.1(4) . . . . ?
 C4 C2 C10 O4 0.8(4) . . . . ?
 C4 C2 C10 N1 -178.4(2) . . . . ?
 C10 N1 C5 O2 179.0(2) . . . . ?
 C10 N1 C5 C1 -1.1(4) . . . 3_666 ?
 C10 N1 C8 P1 -77.7(3) . . . . ?
 C10 C2 C4 C3 179.2(2) . . . . ?
 C5 N1 C10 O4 -179.5(2) . . . . ?
 C5 N1 C10 C2 -0.2(4) . . . . ?
 C5 N1 C8 P1 97.9(2) . . . . ?
 C5 C1 C3 C4 177.8(2) 3_666 . . . ?
 C8 N1 C10 O4 -4.3(4) . . . . ?
 C8 N1 C10 C2 175.0(2) . . . . ?
 C8 N1 C5 O2 4.0(4) . . . . ?
 C8 N1 C5 C1 -176.2(2) . . . 3_666 ?
 C11 N3 C6 N2 0.1(3) . . . . ?
 C7 N2 C6 N3 0.0(3) . . . . ?
 C6 N3 C11 C7 -0.2(3) . . . . ?
 C6 N2 C7 C11 -0.1(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

# END of CIF

data_ABC-2_auto
_audit_creation_date               2024-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C8 H5 N O5 P, C2 H8 N'
_chemical_formula_sum              'C10 H13 N2 O5 P'
_chemical_formula_weight           272.19
_chemical_melting_point            ?
_chemical_oxdiff_formula           ' C N O P'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.2543 0.3332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     4.7632(2)
_cell_length_b                     7.8486(3)
_cell_length_c                     16.4221(7)
_cell_angle_alpha                  100.767(3)
_cell_angle_beta                   98.052(3)
_cell_angle_gamma                  93.767(3)
_cell_volume                       594.51(4)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3630
_cell_measurement_temperature      297.98(10)
_cell_measurement_theta_max        55.0930
_cell_measurement_theta_min        4.9930
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      1.455
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.70289
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour               colorless
_exptl_crystal_density_diffrn      1.521
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description        stick
_exptl_crystal_F_000               284
_exptl_crystal_size_max            0.3
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0594
_diffrn_reflns_av_unetI/netI       0.0656
_diffrn_reflns_Laue_measured_fraction_full  0.992
_diffrn_reflns_Laue_measured_fraction_max  0.973
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              5593
_diffrn_reflns_point_group_measured_fraction_full  0.992
_diffrn_reflns_point_group_measured_fraction_max  0.973
_diffrn_reflns_theta_full          53.543
_diffrn_reflns_theta_max           55.227
_diffrn_reflns_theta_min           2.410
_diffrn_ambient_environment        air
_diffrn_ambient_temperature        297.98(10)
_diffrn_detector                   'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_detector_type              HyPix
_diffrn_measured_fraction_theta_full  0.992
_diffrn_measured_fraction_theta_max  0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     34.00  94.00   0.50    0.05    --   66.75 -77.00 -90.00  120
  2  ω     -2.00  24.00   0.50    0.05    --   66.75 -77.00 -90.00   52
  3  ω     87.00 113.00   0.50    0.05    --   66.75 138.00 -34.00   52
  4  ω     80.00 139.00   0.50    0.05    --   66.75 131.00 149.00  118
  5  ω     39.00 140.00   0.50    0.05    --   66.75  77.00 120.00  202
  6  ω      7.00  90.00   0.50    0.05    --   66.75 -57.00  60.00  166
  7  ω     71.00 106.00   0.50    0.05    --   66.75-138.00 -96.00   70
  8  ω     64.00  98.00   0.50    0.05    --   66.75-125.00 -90.00   68
  9  ω     68.00 115.00   0.50    0.05    --   66.75-131.00  79.00   94
 10  ω    -20.00  24.00   0.50    0.05    --   -0.70  57.00-180.00   88
 11  ω     40.00  67.00   0.50    0.05    --   -0.70  57.00-180.00   54
 12  ω    -69.00   8.00   0.50    0.05    --  -68.15  38.00 -90.00  154
 13  ω    -70.00 -36.00   0.50    0.05    --  -68.15  38.00   0.00   68
 14  ω    -18.00   8.00   0.50    0.05    --  -68.15  38.00   0.00   52
 15  ω   -126.00 -88.00   0.50    0.05    --  -68.15 -99.00 -60.00   76
 16  ω   -119.00 -94.00   0.50    0.05    --  -68.15-125.00 -60.00   50
 17  ω   -118.00 -70.00   0.50    0.05    --  -68.15-138.00 -96.00   96
 18  ω   -140.00 -86.00   0.50    0.05    --  -68.15-125.00  30.00  108
 19  ω   -120.00 -95.00   0.50    0.05    --  -68.15-131.00  79.00   50
 20  ω     -8.00  38.00   0.50    0.05    --   -0.70 -99.00  30.00   92
 21  ω     -8.00  18.00   0.50    0.05    --   -0.70 -99.00-180.00   52
 22  ω   -141.00-104.00   0.50    0.05    --  -68.15 -57.00 120.00   74
 23  ω    -89.00 -63.00   0.50    0.05    --  -68.15 -57.00 120.00   52
 24  ω    -90.00 -64.00   0.50    0.05    --  -68.15 138.00 -34.00   52
 25  ω    -94.00 -69.00   0.50    0.05    --  -68.15 131.00 149.00   50
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0172709000
_diffrn_orient_matrix_UB_12        0.1434012000
_diffrn_orient_matrix_UB_13        -0.0329456000
_diffrn_orient_matrix_UB_21        0.0502421000
_diffrn_orient_matrix_UB_22        0.0990596000
_diffrn_orient_matrix_UB_23        0.0772598000
_diffrn_orient_matrix_UB_31        0.2802392000
_diffrn_orient_matrix_UB_32        0.0078482000
_diffrn_orient_matrix_UB_33        -0.0025894000
_diffrn_oxdiff_digest_frames
;
0130b6f400299cf8061e9a4a58dd3e8aa000042025f
;
_diffrn_oxdiff_digest_hkl
;
0162666212e91ea08f9e4ab68fb708329ff27b
;
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.3405
_diffrn_source                     'micro-focus metaljet'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1900
_reflns_number_total               2235
_reflns_odcompleteness_completeness  99.29
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       53.13
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection         'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_reduction          'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.382
_refine_diff_density_min           -0.516
_refine_diff_density_rms           0.083
_refine_ls_extinction_coef         0.008(2)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       167
_refine_ls_number_reflns           2235
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0561
_refine_ls_R_factor_gt             0.0500
_refine_ls_restrained_S_all        1.046
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0867P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1338
_refine_ls_wR_factor_ref           0.1401
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.55227(9) 1.03262(6) 0.81659(3) 0.0251(2) Uani 1 1 d . . . . .
 O1 O 0.0605(3) 0.71263(19) 0.69227(10) 0.0336(4) Uani 1 1 d . . . . .
 O2 O 0.5207(3) 0.8547(2) 0.83731(10) 0.0370(4) Uani 1 1 d . . . . .
 O3 O 0.7256(3) 1.03178(18) 0.59676(10) 0.0336(4) Uani 1 1 d . . . . .
 O4 O 0.3846(3) 1.1651(2) 0.87022(10) 0.0398(5) Uani 1 1 d . . . . .
 H4 H 0.215152 1.129704 0.861573 0.060 Uiso 1 1 calc GR . . . .
 O5 O 0.8497(3) 1.1112(2) 0.82527(11) 0.0394(4) Uani 1 1 d . . . . .
 N1 N 0.4074(3) 0.8703(2) 0.64900(11) 0.0234(4) Uani 1 1 d . . . . .
 N2 N 0.0147(4) 0.7070(2) 0.87157(12) 0.0336(5) Uani 1 1 d . . . . .
 H2A H -0.135918 0.761742 0.856329 0.040 Uiso 1 1 calc R . . . .
 H2B H 0.157007 0.743472 0.847334 0.040 Uiso 1 1 calc R . . . .
 C1 C 0.4814(4) 0.5740(2) 0.52993(12) 0.0210(4) Uani 1 1 d . . . . .
 C2 C 0.6272(4) 0.7359(2) 0.52889(12) 0.0217(4) Uani 1 1 d . . . . .
 C3 C 0.2968(4) 0.5582(2) 0.58864(12) 0.0227(4) Uani 1 1 d . . . . .
 C4 C 0.2414(4) 0.7157(3) 0.64777(13) 0.0236(5) Uani 1 1 d . . . . .
 C5 C 0.1999(4) 0.2519(3) 0.53010(13) 0.0271(5) Uani 1 1 d . . . . .
 H5 H 0.108309 0.144223 0.531334 0.033 Uiso 1 1 calc R . . . .
 C6 C 0.3639(4) 1.0239(3) 0.71121(13) 0.0252(5) Uani 1 1 d . . . . .
 H6A H 0.161789 1.025176 0.713681 0.030 Uiso 1 1 calc R . . . .
 H6B H 0.425330 1.128058 0.692167 0.030 Uiso 1 1 calc R . . . .
 C7 C 0.1587(4) 0.3984(3) 0.58846(13) 0.0274(5) Uani 1 1 d . . . . .
 H7 H 0.037516 0.387957 0.627366 0.033 Uiso 1 1 calc R . . . .
 C8 C 0.5943(4) 0.8907(2) 0.59306(13) 0.0244(5) Uani 1 1 d . . . . .
 C9 C 0.0967(7) 0.7561(5) 0.96334(19) 0.0654(9) Uani 1 1 d . . . . .
 H9A H 0.169183 0.876682 0.978533 0.098 Uiso 1 1 calc GR . . . .
 H9B H 0.241226 0.685626 0.981356 0.098 Uiso 1 1 calc GR . . . .
 H9C H -0.066846 0.738012 0.989920 0.098 Uiso 1 1 calc GR . . . .
 C10 C -0.0543(7) 0.5188(3) 0.8404(2) 0.0674(9) Uani 1 1 d . . . . .
 H10A H -0.123341 0.496955 0.781238 0.101 Uiso 1 1 calc GR . . . .
 H10B H -0.198301 0.476601 0.869095 0.101 Uiso 1 1 calc GR . . . .
 H10C H 0.113648 0.459807 0.850416 0.101 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O2 1.5009(15) . ?
 P1 O4 1.5678(15) . ?
 P1 O5 1.4844(14) . ?
 P1 C6 1.821(2) . ?
 O1 C4 1.207(2) . ?
 O3 C8 1.222(2) . ?
 N1 C4 1.400(2) . ?
 N1 C6 1.474(2) . ?
 N1 C8 1.388(3) . ?
 N2 C9 1.473(3) . ?
 N2 C10 1.470(3) . ?
 C1 C1 1.412(4) 2_666 ?
 C1 C2 1.412(3) . ?
 C1 C3 1.409(3) . ?
 C2 C5 1.369(3) 2_666 ?
 C2 C8 1.484(3) . ?
 C3 C4 1.486(3) . ?
 C3 C7 1.377(3) . ?
 C5 C7 1.396(3) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O2 P1 O4 111.82(10) . . ?
 O2 P1 C6 108.83(9) . . ?
 O4 P1 C6 101.24(9) . . ?
 O5 P1 O2 115.42(9) . . ?
 O5 P1 O4 107.95(9) . . ?
 O5 P1 C6 110.67(10) . . ?
 C4 N1 C6 116.65(16) . . ?
 C8 N1 C4 124.74(16) . . ?
 C8 N1 C6 118.49(16) . . ?
 C10 N2 C9 113.8(2) . . ?
 C2 C1 C1 119.2(2) . 2_666 ?
 C3 C1 C1 119.6(2) . 2_666 ?
 C3 C1 C2 121.20(18) . . ?
 C1 C2 C8 119.31(18) . . ?
 C5 C2 C1 119.89(19) 2_666 . ?
 C5 C2 C8 120.79(18) 2_666 . ?
 C1 C3 C4 119.76(17) . . ?
 C7 C3 C1 119.92(18) . . ?
 C7 C3 C4 120.26(18) . . ?
 O1 C4 N1 120.99(19) . . ?
 O1 C4 C3 122.24(18) . . ?
 N1 C4 C3 116.77(17) . . ?
 C2 C5 C7 121.09(18) 2_666 . ?
 N1 C6 P1 114.51(13) . . ?
 C3 C7 C5 120.28(19) . . ?
 O3 C8 N1 120.75(18) . . ?
 O3 C8 C2 121.57(18) . . ?
 N1 C8 C2 117.67(17) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.830
_oxdiff_exptl_absorpt_empirical_full_min  0.491

# END of CIF

data_syy1
_audit_creation_date               2026-03-28
_audit_creation_method
;
Olex2 1.5
(compiled 2026.03.20 svn.r2bc28608 for OlexSys, GUI svn.r7530)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C8 H5 N O5 P, H4 N'
_chemical_formula_sum              'C8 H9 N2 O5 P'
_chemical_formula_weight           244.14
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     4.6371(4)
_cell_length_b                     7.4493(6)
_cell_length_c                     14.5081(12)
_cell_angle_alpha                  88.434(4)
_cell_angle_beta                   82.786(4)
_cell_angle_gamma                  77.489(4)
_cell_volume                       485.38(7)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      1478
_cell_measurement_temperature      295.00
_cell_measurement_theta_max        26.67
_cell_measurement_theta_min        2.80
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.292
_exptl_absorpt_correction_T_max    0.7457
_exptl_absorpt_correction_T_min    0.5318
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0902 after correction.
The Ratio of minimum to maximum transmission is 0.7132.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              Colorless
_exptl_crystal_density_diffrn      1.670
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               252
_exptl_crystal_size_max            0.2
_exptl_crystal_size_mid            0.14
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1524
_diffrn_reflns_av_unetI/netI       0.1119
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              9959
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.998
_diffrn_reflns_theta_full          25.026
_diffrn_reflns_theta_max           25.026
_diffrn_reflns_theta_min           2.830
_diffrn_ambient_temperature        295.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             30.0
_diffrn_source_power               1.5
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1104
_reflns_number_total               1725
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.466
_refine_diff_density_min           -0.475
_refine_diff_density_rms           0.101
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.149
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       162
_refine_ls_number_reflns           1725
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.1478
_refine_ls_R_factor_gt             0.0869
_refine_ls_restrained_S_all        1.148
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0366P)²+1.2908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1410
_refine_ls_wR_factor_ref           0.1663
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N2-H2C
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.8041(4) 0.8133(2) 0.84683(11) 0.0227(4) Uani 1 1 d . . . . .
 O4 O 0.9529(9) 0.8743(6) 0.5941(3) 0.0337(11) Uani 1 1 d . . . . .
 O2 O 1.0023(9) 0.9332(5) 0.8748(3) 0.0307(11) Uani 1 1 d . . . . .
 O1 O 0.7101(9) 0.6898(5) 0.9227(3) 0.0321(11) Uani 1 1 d . . . . .
 O3 O 0.5334(9) 0.9320(6) 0.8040(3) 0.0344(11) Uani 1 1 d . . . . .
 H3 H 0.378640 0.922328 0.835984 0.052 Uiso 1 1 calc R U . . .
 O5 O 0.7819(11) 0.3788(6) 0.7621(3) 0.0405(12) Uani 1 1 d . . . . .
 N1 N 0.8670(10) 0.6249(6) 0.6780(3) 0.0215(11) Uani 1 1 d . . . . .
 N2 N 0.8191(15) 1.2878(9) 0.9543(4) 0.0320(14) Uani 1 1 d D . . . .
 C5 C 0.3401(12) 0.2090(7) 0.5536(4) 0.0232(14) Uani 1 1 d . . . . .
 H5 H 0.261439 0.103934 0.559878 0.028 Uiso 1 1 calc R U . . .
 C3 C 0.3107(12) 0.3139(8) 0.4751(4) 0.0213(13) Uani 1 1 d . . . . .
 C1 C 0.5722(12) 0.5251(7) 0.5361(4) 0.0183(13) Uani 1 1 d . . . . .
 C2 C 0.6029(12) 0.4149(7) 0.6161(4) 0.0192(13) Uani 1 1 d . . . . .
 C6 C 0.7560(13) 0.4661(8) 0.6913(4) 0.0223(14) Uani 1 1 d . . . . .
 C7 C 0.4865(12) 0.2574(8) 0.6243(4) 0.0222(14) Uani 1 1 d . . . . .
 H7 H 0.506282 0.184187 0.677079 0.027 Uiso 1 1 calc R U . . .
 C4 C 0.8466(12) 0.7385(8) 0.5991(4) 0.0234(14) Uani 1 1 d . . . . .
 C8 C 1.0285(12) 0.6774(8) 0.7498(4) 0.0241(14) Uani 1 1 d . . . . .
 H8A H 1.169576 0.746688 0.720375 0.029 Uiso 1 1 calc R U . . .
 H8B H 1.142364 0.565978 0.774797 0.029 Uiso 1 1 calc R U . . .
 H2A H 0.865(13) 1.178(9) 0.923(4) 0.032(18) Uiso 1 1 d . . . . .
 H2B H 0.61(3) 1.299(15) 0.993(8) 0.14(4) Uiso 1 1 d . . . . .
 H2C H 0.78(3) 1.385(10) 0.916(6) 0.16(5) Uiso 1 1 d D . . . .
 H2D H 0.963(18) 1.282(10) 0.987(5) 0.06(3) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O2 1.508(4) . ?
 P1 O1 1.498(4) . ?
 P1 O3 1.559(4) . ?
 P1 C8 1.829(6) . ?
 O4 C4 1.214(7) . ?
 O3 H3 0.8200 . ?
 O5 C6 1.205(6) . ?
 N1 C6 1.388(7) . ?
 N1 C4 1.406(7) . ?
 N1 C8 1.464(7) . ?
 N2 H2A 0.92(7) . ?
 N2 H2B 1.03(12) . ?
 N2 H2C 0.90(2) . ?
 N2 H2D 0.86(8) . ?
 C5 H5 0.9300 . ?
 C5 C3 1.368(8) . ?
 C5 C7 1.395(7) . ?
 C3 C1 1.418(7) 2_666 ?
 C3 C4 1.478(8) 2_666 ?
 C1 C1 1.411(11) 2_666 ?
 C1 C2 1.407(7) . ?
 C2 C6 1.475(8) . ?
 C2 C7 1.390(8) . ?
 C7 H7 0.9300 . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O2 P1 O3 110.5(3) . . ?
 O2 P1 C8 104.1(2) . . ?
 O1 P1 O2 114.1(3) . . ?
 O1 P1 O3 112.2(2) . . ?
 O1 P1 C8 110.4(3) . . ?
 O3 P1 C8 104.8(3) . . ?
 P1 O3 H3 109.5 . . ?
 C6 N1 C4 125.4(5) . . ?
 C6 N1 C8 118.3(5) . . ?
 C4 N1 C8 116.3(5) . . ?
 H2A N2 H2B 108(7) . . ?
 H2A N2 H2C 112(8) . . ?
 H2A N2 H2D 104(6) . . ?
 H2B N2 H2C 100(9) . . ?
 H2B N2 H2D 114(8) . . ?
 H2C N2 H2D 118(9) . . ?
 C3 C5 H5 119.6 . . ?
 C3 C5 C7 120.9(5) . . ?
 C7 C5 H5 119.6 . . ?
 C5 C3 C1 120.7(5) . 2_666 ?
 C5 C3 C4 120.3(5) . 2_666 ?
 C1 C3 C4 119.0(5) 2_666 2_666 ?
 C1 C1 C3 118.4(6) 2_666 2_666 ?
 C2 C1 C3 121.3(5) . 2_666 ?
 C2 C1 C1 120.3(6) . 2_666 ?
 C1 C2 C6 120.4(5) . . ?
 C7 C2 C1 119.7(5) . . ?
 C7 C2 C6 119.9(5) . . ?
 O5 C6 N1 120.4(5) . . ?
 O5 C6 C2 123.0(5) . . ?
 N1 C6 C2 116.6(5) . . ?
 C5 C7 H7 119.9 . . ?
 C2 C7 C5 120.1(5) . . ?
 C2 C7 H7 119.9 . . ?
 O4 C4 N1 120.2(5) . . ?
 O4 C4 C3 122.6(5) . 2_666 ?
 N1 C4 C3 117.2(5) . 2_666 ?
 P1 C8 H8A 108.1 . . ?
 P1 C8 H8B 108.1 . . ?
 N1 C8 P1 116.6(4) . . ?
 N1 C8 H8A 108.1 . . ?
 N1 C8 H8B 108.1 . . ?
 H8A C8 H8B 107.3 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O2 P1 C8 N1 -148.3(4) . . . . ?
 O1 P1 C8 N1 88.8(5) . . . . ?
 O3 P1 C8 N1 -32.1(5) . . . . ?
 C3 C5 C7 C2 0.5(8) . . . . ?
 C3 C1 C2 C6 0.7(8) 2_666 . . . ?
 C3 C1 C2 C7 -179.7(5) 2_666 . . . ?
 C1 C1 C2 C6 179.5(6) 2_666 . . . ?
 C1 C1 C2 C7 -0.9(9) 2_666 . . . ?
 C1 C2 C6 O5 178.2(6) . . . . ?
 C1 C2 C6 N1 -0.5(7) . . . . ?
 C1 C2 C7 C5 0.0(8) . . . . ?
 C6 N1 C4 O4 -179.6(5) . . . . ?
 C6 N1 C4 C3 1.2(8) . . . 2_666 ?
 C6 N1 C8 P1 -85.8(6) . . . . ?
 C6 C2 C7 C5 179.7(5) . . . . ?
 C7 C5 C3 C1 -0.2(8) . . . 2_666 ?
 C7 C5 C3 C4 -179.6(5) . . . 2_666 ?
 C7 C2 C6 O5 -1.4(9) . . . . ?
 C7 C2 C6 N1 179.9(5) . . . . ?
 C4 N1 C6 O5 -179.2(5) . . . . ?
 C4 N1 C6 C2 -0.5(8) . . . . ?
 C4 N1 C8 P1 96.3(5) . . . . ?
 C8 N1 C6 O5 3.1(8) . . . . ?
 C8 N1 C6 C2 -178.2(5) . . . . ?
 C8 N1 C4 O4 -1.8(8) . . . . ?
 C8 N1 C4 C3 178.9(5) . . . 2_666 ?

_olex2_submission_special_instructions  'No special instructions were received'

# END of CIF

data_1111
_audit_creation_date               2026-02-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C8 H6 N O5 P, C8 H5 N O5 P, C H6 N3'
_chemical_formula_sum              'C17 H17 N5 O10 P2'
_chemical_formula_weight           513.29
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.5601(3)
_cell_length_b                     8.7126(3)
_cell_length_c                     14.2352(5)
_cell_angle_alpha                  96.8570(10)
_cell_angle_beta                   95.9470(10)
_cell_angle_gamma                  110.1350(10)
_cell_volume                       977.66(6)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9905
_cell_measurement_temperature      294.00
_cell_measurement_theta_max        28.41
_cell_measurement_theta_min        2.53
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.296
_exptl_absorpt_correction_T_max    0.7292
_exptl_absorpt_correction_T_min    0.6265
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0860 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8592.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              Colorless
_exptl_crystal_density_diffrn      1.744
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               528
_exptl_crystal_size_max            0.25
_exptl_crystal_size_mid            0.16
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0558
_diffrn_reflns_av_unetI/netI       0.0336
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              24921
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.435
_diffrn_reflns_theta_min           2.525
_diffrn_ambient_temperature        294.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             30.0
_diffrn_source_power               1.5
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4193
_reflns_number_total               4902
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.597
_refine_diff_density_min           -0.688
_refine_diff_density_rms           0.091
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       313
_refine_ls_number_reflns           4902
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0562
_refine_ls_R_factor_gt             0.0478
_refine_ls_restrained_S_all        1.028
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0744P)²+0.7942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1349
_refine_ls_wR_factor_ref           0.1436
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O5-H5
 0.85 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C3(H3), C7(H7)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3B,H3C), N2(H2A,H2B)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3A)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.48730(6) 0.94348(6) 0.62951(3) 0.02452(14) Uani 1 1 d . . . . .
 P2 P 0.49095(6) 0.55819(6) 0.86542(4) 0.02593(14) Uani 1 1 d . . . . .
 O1 O 0.42787(18) 0.13468(19) 0.86421(11) 0.0330(3) Uani 1 1 d . . . . .
 O4 O 0.39724(18) 0.83147(19) 0.69925(11) 0.0338(3) Uani 1 1 d . . . . .
 H4 H 0.458926 0.786643 0.721937 0.051 Uiso 1 1 calc R U . . .
 O6 O 0.58907(19) 1.37439(19) 0.64951(12) 0.0347(3) Uani 1 1 d . . . . .
 O8 O 0.63857(18) 0.52417(19) 0.91248(11) 0.0332(3) Uani 1 1 d . . . . .
 O10 O 0.5528(2) 0.85355(19) 0.55560(11) 0.0339(3) Uani 1 1 d . . . . .
 O5 O 0.35389(19) 1.0078(2) 0.58766(12) 0.0351(3) Uani 1 1 d D . . . .
 O3 O 0.3963(2) 0.62240(19) 0.93914(11) 0.0348(3) Uani 1 1 d . . . . .
 H3A H 0.385604 0.567803 0.982751 0.052 Uiso 1 1 calc R U . . .
 O7 O 0.54066(19) 0.68352(19) 0.79812(12) 0.0367(4) Uani 1 1 d . . . . .
 O2 O 0.0370(2) 0.3778(2) 0.83691(12) 0.0382(4) Uani 1 1 d . . . . .
 O9 O 0.9491(2) 1.0947(2) 0.64172(13) 0.0419(4) Uani 1 1 d . . . . .
 N1 N 0.8185(2) 0.8255(2) 0.75905(14) 0.0339(4) Uani 1 1 d . . . . .
 H1A H 0.732517 0.782481 0.786492 0.041 Uiso 1 1 calc R U . . .
 H1B H 0.824468 0.907128 0.729244 0.041 Uiso 1 1 calc R U . . .
 N4 N 0.23546(19) 0.26035(19) 0.85364(11) 0.0237(3) Uani 1 1 d . . . . .
 N5 N 0.76151(19) 1.22632(19) 0.63981(11) 0.0232(3) Uani 1 1 d . . . . .
 N3 N 0.9308(2) 0.6444(2) 0.80741(14) 0.0373(4) Uani 1 1 d . . . . .
 H3B H 0.845512 0.600214 0.835169 0.045 Uiso 1 1 calc R U . . .
 H3C H 1.011670 0.607074 0.809210 0.045 Uiso 1 1 calc R U . . .
 N2 N 1.0646(2) 0.8432(2) 0.71870(14) 0.0375(4) Uani 1 1 d . . . . .
 H2A H 1.063389 0.924755 0.690405 0.045 Uiso 1 1 calc R U . . .
 H2B H 1.148562 0.810410 0.718501 0.045 Uiso 1 1 calc R U . . .
 C1 C -0.1995(2) -0.0370(2) 1.05057(13) 0.0214(3) Uani 1 1 d . . . . .
 C4 C 1.1937(2) 1.5338(2) 0.44368(13) 0.0213(3) Uani 1 1 d . . . . .
 C6 C 0.2987(2) 0.1442(2) 0.88670(13) 0.0223(3) Uani 1 1 d . . . . .
 C8 C -0.0123(2) 0.1693(2) 0.93435(13) 0.0224(3) Uani 1 1 d . . . . .
 C10 C -0.1607(2) 0.1827(2) 0.95672(14) 0.0263(4) Uani 1 1 d . . . . .
 H10 H -0.198644 0.260650 0.932977 0.032 Uiso 1 1 calc R U . . .
 C12 C -0.2544(2) 0.0791(2) 1.01520(14) 0.0260(4) Uani 1 1 d . . . . .
 H12 H -0.354171 0.088903 1.030147 0.031 Uiso 1 1 calc R U . . .
 C14 C 1.0061(2) 1.3191(2) 0.55610(13) 0.0231(4) Uani 1 1 d . . . . .
 C16 C 0.9526(2) 1.4458(2) 0.52855(12) 0.0200(3) Uani 1 1 d . . . . .
 C17 C 0.6632(2) 1.1145(2) 0.70054(13) 0.0254(4) Uani 1 1 d . . . . .
 H17A H 0.621216 1.177022 0.745867 0.030 Uiso 1 1 calc R U . . .
 H17B H 0.736242 1.071104 0.736649 0.030 Uiso 1 1 calc R U . . .
 C9 C 0.0477(2) 0.0527(2) 0.97090(12) 0.0198(3) Uani 1 1 d . . . . .
 C5 C 0.7083(2) 1.3555(2) 0.61803(13) 0.0229(3) Uani 1 1 d . . . . .
 C11 C 0.9066(2) 1.2036(2) 0.61511(14) 0.0257(4) Uani 1 1 d . . . . .
 C3 C 1.1504(2) 1.3024(2) 0.52877(15) 0.0284(4) Uani 1 1 d . . . . .
 H3 H 1.185431 1.219564 0.547941 0.034 Uiso 1 1 calc R U . . .
 C13 C 0.3351(2) 0.3711(2) 0.79388(13) 0.0267(4) Uani 1 1 d . . . . .
 H13A H 0.260216 0.401257 0.750083 0.032 Uiso 1 1 calc R U . . .
 H13B H 0.391652 0.312764 0.756030 0.032 Uiso 1 1 calc R U . . .
 C7 C 1.2444(2) 1.4101(2) 0.47216(15) 0.0270(4) Uani 1 1 d . . . . .
 H7 H 1.341185 1.397919 0.453772 0.032 Uiso 1 1 calc R U . . .
 C15 C 0.0852(2) 0.2779(2) 0.87204(14) 0.0247(4) Uani 1 1 d . . . . .
 C2 C 0.9374(2) 0.7682(2) 0.76254(15) 0.0307(4) Uani 1 1 d . . . . .
 H5 H 0.376(6) 1.055(5) 0.537(2) 0.117(16) Uiso 1 1 d D . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O4 1.5506(14) . ?
 P1 O10 1.5044(15) . ?
 P1 O5 1.5338(15) . ?
 P1 C17 1.814(2) . ?
 P2 O8 1.5044(15) . ?
 P2 O3 1.5550(15) . ?
 P2 O7 1.5184(14) . ?
 P2 C13 1.816(2) . ?
 O1 C6 1.209(2) . ?
 O4 H4 0.8200 . ?
 O6 C5 1.209(2) . ?
 O5 H5 0.879(19) . ?
 O3 H3A 0.8200 . ?
 O2 C15 1.220(2) . ?
 O9 C11 1.213(2) . ?
 N1 H1A 0.8600 . ?
 N1 H1B 0.8600 . ?
 N1 C2 1.277(3) . ?
 N4 C6 1.406(2) . ?
 N4 C13 1.471(2) . ?
 N4 C15 1.393(2) . ?
 N5 C17 1.481(2) . ?
 N5 C5 1.406(2) . ?
 N5 C11 1.395(2) . ?
 N3 H3B 0.8600 . ?
 N3 H3C 0.8600 . ?
 N3 C2 1.306(3) . ?
 N2 H2A 0.8600 . ?
 N2 H2B 0.8600 . ?
 N2 C2 1.323(3) . ?
 C1 C6 1.484(2) 2_557 ?
 C1 C12 1.378(2) . ?
 C1 C9 1.412(2) 2_557 ?
 C4 C16 1.413(2) 2_786 ?
 C4 C5 1.484(2) 2_786 ?
 C4 C7 1.380(2) . ?
 C8 C10 1.380(2) . ?
 C8 C9 1.413(2) . ?
 C8 C15 1.479(2) . ?
 C10 H10 0.9300 . ?
 C10 C12 1.404(3) . ?
 C12 H12 0.9300 . ?
 C14 C16 1.413(2) . ?
 C14 C11 1.485(2) . ?
 C14 C3 1.381(2) . ?
 C16 C16 1.415(3) 2_786 ?
 C17 H17A 0.9700 . ?
 C17 H17B 0.9700 . ?
 C9 C9 1.415(3) 2_557 ?
 C3 H3 0.9300 . ?
 C3 C7 1.404(3) . ?
 C13 H13A 0.9700 . ?
 C13 H13B 0.9700 . ?
 C7 H7 0.9300 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O4 P1 C17 107.44(9) . . ?
 O10 P1 O4 112.78(9) . . ?
 O10 P1 O5 114.15(9) . . ?
 O10 P1 C17 108.85(9) . . ?
 O5 P1 O4 103.59(8) . . ?
 O5 P1 C17 109.76(9) . . ?
 O8 P2 O3 112.65(9) . . ?
 O8 P2 O7 112.78(8) . . ?
 O8 P2 C13 111.28(9) . . ?
 O3 P2 C13 105.74(9) . . ?
 O7 P2 O3 107.65(9) . . ?
 O7 P2 C13 106.27(9) . . ?
 P1 O4 H4 109.5 . . ?
 P1 O5 H5 115(3) . . ?
 P2 O3 H3A 109.5 . . ?
 H1A N1 H1B 120.0 . . ?
 C2 N1 H1A 120.0 . . ?
 C2 N1 H1B 120.0 . . ?
 C6 N4 C13 117.31(15) . . ?
 C15 N4 C6 125.32(15) . . ?
 C15 N4 C13 117.36(15) . . ?
 C5 N5 C17 117.04(15) . . ?
 C11 N5 C17 117.67(15) . . ?
 C11 N5 C5 125.08(15) . . ?
 H3B N3 H3C 120.0 . . ?
 C2 N3 H3B 120.0 . . ?
 C2 N3 H3C 120.0 . . ?
 H2A N2 H2B 120.0 . . ?
 C2 N2 H2A 120.0 . . ?
 C2 N2 H2B 120.0 . . ?
 C12 C1 C6 119.79(16) . 2_557 ?
 C12 C1 C9 120.53(16) . 2_557 ?
 C9 C1 C6 119.68(15) 2_557 2_557 ?
 C16 C4 C5 119.64(15) 2_786 2_786 ?
 C7 C4 C16 120.47(16) . 2_786 ?
 C7 C4 C5 119.88(16) . 2_786 ?
 O1 C6 N4 120.50(16) . . ?
 O1 C6 C1 122.85(16) . 2_557 ?
 N4 C6 C1 116.65(15) . 2_557 ?
 C10 C8 C9 120.41(16) . . ?
 C10 C8 C15 119.99(16) . . ?
 C9 C8 C15 119.59(15) . . ?
 C8 C10 H10 119.9 . . ?
 C8 C10 C12 120.22(16) . . ?
 C12 C10 H10 119.9 . . ?
 C1 C12 C10 120.36(16) . . ?
 C1 C12 H12 119.8 . . ?
 C10 C12 H12 119.8 . . ?
 C16 C14 C11 119.62(16) . . ?
 C3 C14 C16 120.47(16) . . ?
 C3 C14 C11 119.92(16) . . ?
 C4 C16 C16 119.27(19) 2_786 2_786 ?
 C14 C16 C4 121.50(15) . 2_786 ?
 C14 C16 C16 119.23(19) . 2_786 ?
 P1 C17 H17A 109.3 . . ?
 P1 C17 H17B 109.3 . . ?
 N5 C17 P1 111.65(12) . . ?
 N5 C17 H17A 109.3 . . ?
 N5 C17 H17B 109.3 . . ?
 H17A C17 H17B 108.0 . . ?
 C1 C9 C8 121.53(16) 2_557 . ?
 C1 C9 C9 119.17(19) 2_557 2_557 ?
 C8 C9 C9 119.29(19) . 2_557 ?
 O6 C5 N5 120.61(16) . . ?
 O6 C5 C4 122.57(16) . 2_786 ?
 N5 C5 C4 116.81(15) . 2_786 ?
 O9 C11 N5 120.95(17) . . ?
 O9 C11 C14 121.93(17) . . ?
 N5 C11 C14 117.12(16) . . ?
 C14 C3 H3 119.9 . . ?
 C14 C3 C7 120.28(17) . . ?
 C7 C3 H3 119.9 . . ?
 P2 C13 H13A 109.2 . . ?
 P2 C13 H13B 109.2 . . ?
 N4 C13 P2 111.95(13) . . ?
 N4 C13 H13A 109.2 . . ?
 N4 C13 H13B 109.2 . . ?
 H13A C13 H13B 107.9 . . ?
 C4 C7 C3 120.27(16) . . ?
 C4 C7 H7 119.9 . . ?
 C3 C7 H7 119.9 . . ?
 O2 C15 N4 120.65(17) . . ?
 O2 C15 C8 122.16(17) . . ?
 N4 C15 C8 117.18(15) . . ?
 N1 C2 N3 121.0(2) . . ?
 N1 C2 N2 115.54(19) . . ?
 N3 C2 N2 123.5(2) . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O4 P1 C17 N5 178.04(12) . . . . ?
 O8 P2 C13 N4 75.89(15) . . . . ?
 O10 P1 C17 N5 55.62(15) . . . . ?
 O5 P1 C17 N5 -69.97(15) . . . . ?
 O3 P2 C13 N4 -46.74(15) . . . . ?
 O7 P2 C13 N4 -160.97(13) . . . . ?
 C6 N4 C13 P2 -88.35(18) . . . . ?
 C6 N4 C15 O2 -176.92(19) . . . . ?
 C6 N4 C15 C8 2.3(3) . . . . ?
 C6 C1 C12 C10 179.22(17) 2_557 . . . ?
 C8 C10 C12 C1 -0.1(3) . . . . ?
 C10 C8 C9 C1 -179.72(18) . . . 2_557 ?
 C10 C8 C9 C9 1.3(3) . . . 2_557 ?
 C10 C8 C15 O2 -1.9(3) . . . . ?
 C10 C8 C15 N4 178.82(18) . . . . ?
 C14 C3 C7 C4 0.3(3) . . . . ?
 C16 C4 C7 C3 0.3(3) 2_786 . . . ?
 C16 C14 C11 O9 -178.8(2) . . . . ?
 C16 C14 C11 N5 0.6(3) . . . . ?
 C16 C14 C3 C7 -0.8(3) . . . . ?
 C17 N5 C5 O6 1.2(3) . . . . ?
 C17 N5 C5 C4 -179.39(15) . . . 2_786 ?
 C17 N5 C11 O9 0.8(3) . . . . ?
 C17 N5 C11 C14 -178.60(16) . . . . ?
 C9 C1 C12 C10 0.4(3) 2_557 . . . ?
 C9 C8 C10 C12 -0.7(3) . . . . ?
 C9 C8 C15 O2 178.29(19) . . . . ?
 C9 C8 C15 N4 -0.9(3) . . . . ?
 C5 N5 C17 P1 87.73(18) . . . . ?
 C5 N5 C11 O9 175.43(19) . . . . ?
 C5 N5 C11 C14 -4.0(3) . . . . ?
 C5 C4 C7 C3 -178.56(18) 2_786 . . . ?
 C11 N5 C17 P1 -97.24(17) . . . . ?
 C11 N5 C5 O6 -173.39(19) . . . . ?
 C11 N5 C5 C4 6.0(3) . . . 2_786 ?
 C11 C14 C16 C4 0.3(3) . . . 2_786 ?
 C11 C14 C16 C16 -179.3(2) . . . 2_786 ?
 C11 C14 C3 C7 179.37(18) . . . . ?
 C3 C14 C16 C4 -179.46(18) . . . 2_786 ?
 C3 C14 C16 C16 0.9(3) . . . 2_786 ?
 C3 C14 C11 O9 1.0(3) . . . . ?
 C3 C14 C11 N5 -179.58(18) . . . . ?
 C13 N4 C6 O1 -1.8(3) . . . . ?
 C13 N4 C6 C1 178.12(15) . . . 2_557 ?
 C13 N4 C15 O2 2.4(3) . . . . ?
 C13 N4 C15 C8 -178.38(16) . . . . ?
 C15 N4 C6 O1 177.47(18) . . . . ?
 C15 N4 C6 C1 -2.6(3) . . . 2_557 ?
 C15 N4 C13 P2 92.30(18) . . . . ?
 C15 C8 C10 C12 179.49(18) . . . . ?
 C15 C8 C9 C1 0.0(3) . . . 2_557 ?
 C15 C8 C9 C9 -178.9(2) . . . 2_557 ?

_olex2_submission_special_instructions  'No special instructions were received'

# END of CIF

data_abc-5
_audit_creation_date               2026-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2026.04.03 svn.r6693cd53 for OlexSys, GUI svn.r7533)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C16 H12 N2 O10 P2, H2 O'
_chemical_formula_sum              'C16 H14 N2 O11 P2'
_chemical_formula_weight           472.23
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     8.4004(3)
_cell_length_b                     11.4656(4)
_cell_length_c                     18.4447(5)
_cell_angle_alpha                  90
_cell_angle_beta                   100.6270(10)
_cell_angle_gamma                  90
_cell_volume                       1746.04(10)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6591
_cell_measurement_temperature      295.00
_cell_measurement_theta_max        28.22
_cell_measurement_theta_min        2.47
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.323
_exptl_absorpt_correction_T_max    0.6801
_exptl_absorpt_correction_T_min    0.5307
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0908 after correction.
The Ratio of minimum to maximum transmission is 0.7803.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              Colorless
_exptl_crystal_density_diffrn      1.796
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               968
_exptl_crystal_size_max            0.21
_exptl_crystal_size_mid            0.16
_exptl_crystal_size_min            0.09
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1086
_diffrn_reflns_av_unetI/netI       0.0651
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         24
_diffrn_reflns_limit_l_min         -24
_diffrn_reflns_number              33013
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.998
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.314
_diffrn_reflns_theta_min           2.102
_diffrn_ambient_temperature        295.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             30.0
_diffrn_source_power               1.5
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2927
_reflns_number_total               4332
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.418
_refine_diff_density_min           -0.402
_refine_diff_density_rms           0.089
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.140
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       291
_refine_ls_number_reflns           4332
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.1147
_refine_ls_R_factor_gt             0.0683
_refine_ls_restrained_S_all        1.140
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1646
_refine_ls_wR_factor_ref           0.1920
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O11-H11B
 0.85 with sigma of 0.02
3.a Free rotating group:
 O11(H11A)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C5(H5), C14(H14)
3.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O4(H4), O10(H10), O9(H9)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.76826(11) 0.23100(8) 0.72380(5) 0.0243(2) Uani 1 1 d . . . . .
 P2 P 0.21977(12) 1.09925(8) 0.67074(5) 0.0265(3) Uani 1 1 d . . . . .
 O2 O 0.4345(3) 0.3032(2) 0.58230(14) 0.0322(6) Uani 1 1 d . . . . .
 O8 O 0.8288(3) 0.1026(2) 0.73129(15) 0.0304(6) Uani 1 1 d . . . . .
 H8 H 0.921219 0.099271 0.722907 0.046 Uiso 1 1 calc R U . . .
 O1 O 0.0705(3) 0.8600(2) 0.54632(15) 0.0357(6) Uani 1 1 d . . . . .
 O4 O 0.9015(3) 0.3036(2) 0.77212(15) 0.0349(6) Uani 1 1 d . . . . .
 H4 H 0.870746 0.371210 0.773856 0.052 Uiso 1 1 calc R U . . .
 O6 O 0.0977(3) 1.0215(2) 0.69682(15) 0.0358(7) Uani 1 1 d . . . . .
 O5 O 0.5679(3) 1.0274(2) 0.58877(17) 0.0387(7) Uani 1 1 d . . . . .
 O3 O 0.9315(3) 0.4713(2) 0.62890(16) 0.0372(7) Uani 1 1 d . . . . .
 O7 O 0.6064(3) 0.2403(2) 0.74584(14) 0.0346(6) Uani 1 1 d . . . . .
 O10 O 0.1558(3) 1.2254(2) 0.66270(16) 0.0368(7) Uani 1 1 d . . . . .
 H10 H 0.223458 1.269558 0.685950 0.055 Uiso 1 1 calc R U . . .
 O9 O 0.3839(3) 1.0886(2) 0.72375(15) 0.0373(7) Uani 1 1 d . . . . .
 H9 H 0.439977 1.145610 0.718973 0.056 Uiso 1 1 calc R U . . .
 N1 N 0.6820(3) 0.3882(2) 0.61435(15) 0.0229(6) Uani 1 1 d . . . . .
 N2 N 0.3199(3) 0.9431(2) 0.57761(15) 0.0239(6) Uani 1 1 d . . . . .
 O11 O 0.6755(5) 0.8912(3) 0.7716(2) 0.0527(9) Uani 1 1 d DG . . . .
 H11A H 0.713928 0.953066 0.756208 0.079 Uiso 1 1 d G U . . .
 C1 C 0.4647(4) 0.7214(3) 0.58278(17) 0.0198(7) Uani 1 1 d . . . . .
 C4 C 0.4384(4) 0.5097(3) 0.58245(17) 0.0194(7) Uani 1 1 d . . . . .
 C2 C 0.7077(4) 0.6011(3) 0.60726(18) 0.0210(7) Uani 1 1 d . . . . .
 C7 C 0.5635(4) 0.8212(3) 0.59004(18) 0.0228(7) Uani 1 1 d . . . . .
 C8 C 0.5373(4) 0.6091(3) 0.59055(17) 0.0213(7) Uani 1 1 d . . . . .
 C6 C 0.2713(4) 0.5200(3) 0.56540(19) 0.0246(7) Uani 1 1 d . . . . .
 H6 H 0.206748 0.453567 0.559494 0.029 Uiso 1 1 calc R U . . .
 C10 C 0.2160(4) 0.8465(3) 0.56167(19) 0.0249(7) Uani 1 1 d . . . . .
 C11 C 0.1996(4) 0.6309(3) 0.55705(18) 0.0248(7) Uani 1 1 d . . . . .
 H11 H 0.087486 0.637508 0.545027 0.030 Uiso 1 1 calc R U . . .
 C13 C 0.2945(4) 0.7306(3) 0.56659(17) 0.0210(7) Uani 1 1 d . . . . .
 C15 C 0.7863(4) 0.4848(3) 0.61766(18) 0.0235(7) Uani 1 1 d . . . . .
 C3 C 0.5128(4) 0.3926(3) 0.59215(18) 0.0234(7) Uani 1 1 d . . . . .
 C5 C 0.8017(4) 0.6999(3) 0.61403(19) 0.0253(7) Uani 1 1 d . . . . .
 H5 H 0.913928 0.693433 0.624390 0.030 Uiso 1 1 calc R U . . .
 C12 C 0.4888(4) 0.9381(3) 0.58496(18) 0.0242(7) Uani 1 1 d . . . . .
 C14 C 0.7293(4) 0.8108(3) 0.6054(2) 0.0270(8) Uani 1 1 d . . . . .
 H14 H 0.793750 0.877311 0.610097 0.032 Uiso 1 1 calc R U . . .
 C9 C 0.7563(4) 0.2725(3) 0.62855(18) 0.0251(7) Uani 1 1 d . . . . .
 H9A H 0.864250 0.273568 0.616869 0.030 Uiso 1 1 calc R U . . .
 H9B H 0.692558 0.215397 0.596911 0.030 Uiso 1 1 calc R U . . .
 C16 C 0.2453(4) 1.0587(3) 0.57932(19) 0.0272(8) Uani 1 1 d . . . . .
 H16A H 0.140441 1.058693 0.546785 0.033 Uiso 1 1 calc R U . . .
 H16B H 0.312704 1.116329 0.561024 0.033 Uiso 1 1 calc R U . . .
 H11B H 0.580(5) 0.883(7) 0.746(4) 0.17(4) Uiso 1 1 d D . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O8 1.555(2) . ?
 P1 O4 1.540(3) . ?
 P1 O7 1.493(3) . ?
 P1 C9 1.805(3) . ?
 P2 O6 1.503(3) . ?
 P2 O10 1.541(3) . ?
 P2 O9 1.541(3) . ?
 P2 C16 1.800(4) . ?
 O2 C3 1.213(4) . ?
 O8 H8 0.8200 . ?
 O1 C10 1.213(4) . ?
 O4 H4 0.8200 . ?
 O5 C12 1.215(4) . ?
 O3 C15 1.209(4) . ?
 O10 H10 0.8200 . ?
 O9 H9 0.8200 . ?
 N1 C15 1.406(4) . ?
 N1 C3 1.406(4) . ?
 N1 C9 1.469(4) . ?
 N2 C10 1.407(4) . ?
 N2 C12 1.402(4) . ?
 N2 C16 1.470(4) . ?
 O11 H11A 0.8500 . ?
 O11 H11B 0.86(2) . ?
 C1 C7 1.405(4) . ?
 C1 C8 1.421(4) . ?
 C1 C13 1.410(4) . ?
 C4 C8 1.402(4) . ?
 C4 C6 1.386(5) . ?
 C4 C3 1.478(4) . ?
 C2 C8 1.410(4) . ?
 C2 C15 1.484(4) . ?
 C2 C5 1.374(5) . ?
 C7 C12 1.476(5) . ?
 C7 C14 1.375(5) . ?
 C6 H6 0.9300 . ?
 C6 C11 1.402(5) . ?
 C10 C13 1.478(4) . ?
 C11 H11 0.9300 . ?
 C11 C13 1.387(5) . ?
 C5 H5 0.9300 . ?
 C5 C14 1.406(5) . ?
 C14 H14 0.9300 . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C16 H16A 0.9700 . ?
 C16 H16B 0.9700 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O8 P1 C9 107.13(15) . . ?
 O4 P1 O8 105.61(15) . . ?
 O4 P1 C9 108.96(16) . . ?
 O7 P1 O8 110.05(15) . . ?
 O7 P1 O4 113.89(16) . . ?
 O7 P1 C9 110.86(16) . . ?
 O6 P2 O10 109.98(15) . . ?
 O6 P2 O9 109.46(16) . . ?
 O6 P2 C16 110.66(17) . . ?
 O10 P2 C16 104.58(16) . . ?
 O9 P2 O10 112.99(16) . . ?
 O9 P2 C16 109.08(17) . . ?
 P1 O8 H8 109.5 . . ?
 P1 O4 H4 109.5 . . ?
 P2 O10 H10 109.5 . . ?
 P2 O9 H9 109.5 . . ?
 C15 N1 C9 117.6(3) . . ?
 C3 N1 C15 124.9(3) . . ?
 C3 N1 C9 117.3(3) . . ?
 C10 N2 C16 117.7(3) . . ?
 C12 N2 C10 124.5(3) . . ?
 C12 N2 C16 117.5(3) . . ?
 H11A O11 H11B 106.6 . . ?
 C7 C1 C8 119.5(3) . . ?
 C7 C1 C13 121.2(3) . . ?
 C13 C1 C8 119.3(3) . . ?
 C8 C4 C3 119.8(3) . . ?
 C6 C4 C8 120.7(3) . . ?
 C6 C4 C3 119.6(3) . . ?
 C8 C2 C15 119.7(3) . . ?
 C5 C2 C8 120.6(3) . . ?
 C5 C2 C15 119.7(3) . . ?
 C1 C7 C12 119.8(3) . . ?
 C14 C7 C1 120.5(3) . . ?
 C14 C7 C12 119.6(3) . . ?
 C4 C8 C1 119.4(3) . . ?
 C4 C8 C2 121.9(3) . . ?
 C2 C8 C1 118.7(3) . . ?
 C4 C6 H6 120.0 . . ?
 C4 C6 C11 119.9(3) . . ?
 C11 C6 H6 120.0 . . ?
 O1 C10 N2 120.5(3) . . ?
 O1 C10 C13 123.2(3) . . ?
 N2 C10 C13 116.3(3) . . ?
 C6 C11 H11 119.7 . . ?
 C13 C11 C6 120.6(3) . . ?
 C13 C11 H11 119.7 . . ?
 C1 C13 C10 120.2(3) . . ?
 C11 C13 C1 120.1(3) . . ?
 C11 C13 C10 119.6(3) . . ?
 O3 C15 N1 120.5(3) . . ?
 O3 C15 C2 123.2(3) . . ?
 N1 C15 C2 116.3(3) . . ?
 O2 C3 N1 120.3(3) . . ?
 O2 C3 C4 122.9(3) . . ?
 N1 C3 C4 116.8(3) . . ?
 C2 C5 H5 119.8 . . ?
 C2 C5 C14 120.5(3) . . ?
 C14 C5 H5 119.8 . . ?
 O5 C12 N2 120.3(3) . . ?
 O5 C12 C7 122.7(3) . . ?
 N2 C12 C7 117.0(3) . . ?
 C7 C14 C5 120.2(3) . . ?
 C7 C14 H14 119.9 . . ?
 C5 C14 H14 119.9 . . ?
 P1 C9 H9A 109.5 . . ?
 P1 C9 H9B 109.5 . . ?
 N1 C9 P1 110.9(2) . . ?
 N1 C9 H9A 109.5 . . ?
 N1 C9 H9B 109.5 . . ?
 H9A C9 H9B 108.0 . . ?
 P2 C16 H16A 109.2 . . ?
 P2 C16 H16B 109.2 . . ?
 N2 C16 P2 112.2(2) . . ?
 N2 C16 H16A 109.2 . . ?
 N2 C16 H16B 109.2 . . ?
 H16A C16 H16B 107.9 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O8 P1 C9 N1 173.4(2) . . . . ?
 O1 C10 C13 C1 178.3(3) . . . . ?
 O1 C10 C13 C11 -3.3(5) . . . . ?
 O4 P1 C9 N1 -72.8(3) . . . . ?
 O6 P2 C16 N2 -66.7(3) . . . . ?
 O7 P1 C9 N1 53.3(3) . . . . ?
 O10 P2 C16 N2 175.0(2) . . . . ?
 O9 P2 C16 N2 53.8(3) . . . . ?
 N2 C10 C13 C1 -3.1(4) . . . . ?
 N2 C10 C13 C11 175.2(3) . . . . ?
 C1 C7 C12 O5 -177.9(3) . . . . ?
 C1 C7 C12 N2 4.0(5) . . . . ?
 C1 C7 C14 C5 0.0(5) . . . . ?
 C4 C6 C11 C13 -0.8(5) . . . . ?
 C2 C5 C14 C7 0.0(5) . . . . ?
 C7 C1 C8 C4 -179.3(3) . . . . ?
 C7 C1 C8 C2 1.6(5) . . . . ?
 C7 C1 C13 C10 -4.0(5) . . . . ?
 C7 C1 C13 C11 177.7(3) . . . . ?
 C8 C1 C7 C12 -177.6(3) . . . . ?
 C8 C1 C7 C14 -0.7(5) . . . . ?
 C8 C1 C13 C10 177.2(3) . . . . ?
 C8 C1 C13 C11 -1.2(5) . . . . ?
 C8 C4 C6 C11 -0.9(5) . . . . ?
 C8 C4 C3 O2 -176.2(3) . . . . ?
 C8 C4 C3 N1 4.3(5) . . . . ?
 C8 C2 C15 O3 176.7(3) . . . . ?
 C8 C2 C15 N1 -3.8(4) . . . . ?
 C8 C2 C5 C14 0.9(5) . . . . ?
 C6 C4 C8 C1 1.4(5) . . . . ?
 C6 C4 C8 C2 -179.4(3) . . . . ?
 C6 C4 C3 O2 3.8(5) . . . . ?
 C6 C4 C3 N1 -175.7(3) . . . . ?
 C6 C11 C13 C1 1.8(5) . . . . ?
 C6 C11 C13 C10 -176.6(3) . . . . ?
 C10 N2 C12 O5 169.9(3) . . . . ?
 C10 N2 C12 C7 -11.9(5) . . . . ?
 C10 N2 C16 P2 93.3(3) . . . . ?
 C13 C1 C7 C12 3.6(5) . . . . ?
 C13 C1 C7 C14 -179.6(3) . . . . ?
 C13 C1 C8 C4 -0.4(5) . . . . ?
 C13 C1 C8 C2 -179.6(3) . . . . ?
 C15 N1 C3 O2 170.9(3) . . . . ?
 C15 N1 C3 C4 -9.6(5) . . . . ?
 C15 N1 C9 P1 95.4(3) . . . . ?
 C15 C2 C8 C1 178.3(3) . . . . ?
 C15 C2 C8 C4 -0.8(5) . . . . ?
 C15 C2 C5 C14 -179.1(3) . . . . ?
 C3 N1 C15 O3 -171.2(3) . . . . ?
 C3 N1 C15 C2 9.3(5) . . . . ?
 C3 N1 C9 P1 -90.1(3) . . . . ?
 C3 C4 C8 C1 -178.6(3) . . . . ?
 C3 C4 C8 C2 0.5(5) . . . . ?
 C3 C4 C6 C11 179.2(3) . . . . ?
 C5 C2 C8 C1 -1.6(5) . . . . ?
 C5 C2 C8 C4 179.2(3) . . . . ?
 C5 C2 C15 O3 -3.3(5) . . . . ?
 C5 C2 C15 N1 176.2(3) . . . . ?
 C12 N2 C10 O1 -170.0(3) . . . . ?
 C12 N2 C10 C13 11.4(5) . . . . ?
 C12 N2 C16 P2 -92.7(3) . . . . ?
 C12 C7 C14 C5 176.8(3) . . . . ?
 C14 C7 C12 O5 5.2(5) . . . . ?
 C14 C7 C12 N2 -172.9(3) . . . . ?
 C9 N1 C15 O3 2.9(5) . . . . ?
 C9 N1 C15 C2 -176.7(3) . . . . ?
 C9 N1 C3 O2 -3.2(5) . . . . ?
 C9 N1 C3 C4 176.4(3) . . . . ?
 C16 N2 C10 O1 3.6(5) . . . . ?
 C16 N2 C10 C13 -175.0(3) . . . . ?
 C16 N2 C12 O5 -3.6(5) . . . . ?
 C16 N2 C12 C7 174.5(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

# END of CIF
