data_220128a
_audit_creation_date               2022-02-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_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. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C22 H17 O3 P'
_chemical_formula_sum              'C22 H17 O3 P'
_chemical_formula_weight           360.32
_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'
 '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                     5.8638(6)
_cell_length_b                     22.871(2)
_cell_length_c                     14.5987(14)
_cell_angle_alpha                  90
_cell_angle_beta                   97.316(3)
_cell_angle_gamma                  90
_cell_volume                       1941.9(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      722
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        27.168
_cell_measurement_theta_min        2.272
_shelx_estimated_absorpt_T_max     0.995
_shelx_estimated_absorpt_T_min     0.883
_exptl_absorpt_coefficient_mu      0.159
_exptl_absorpt_correction_T_max    0.9953
_exptl_absorpt_correction_T_min    0.8835
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     sadabs
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_lustre       .
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.232
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               752
_exptl_crystal_size_max            0.8
_exptl_crystal_size_mid            0.07
_exptl_crystal_size_min            0.03
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    ?
_diffrn_reflns_av_unetI/netI       0.3406
_diffrn_reflns_Laue_measured_fraction_full  0.990
_diffrn_reflns_Laue_measured_fraction_max  0.990
_diffrn_reflns_limit_h_max         6
_diffrn_reflns_limit_h_min         -6
_diffrn_reflns_limit_k_max         27
_diffrn_reflns_limit_k_min         0
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         0
_diffrn_reflns_number              3380
_diffrn_reflns_point_group_measured_fraction_full  0.990
_diffrn_reflns_point_group_measured_fraction_max  0.990
_diffrn_reflns_theta_full          25.019
_diffrn_reflns_theta_max           25.019
_diffrn_reflns_theta_min           2.269
_diffrn_ambient_temperature        293(2)
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.990
_diffrn_measured_fraction_theta_max  0.990
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1080
_reflns_number_total               3380
_reflns_special_details
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SMART'
_computing_data_collection         'Bruker SMART'
_computing_data_reduction          'Bruker SHELXTL'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max           0.199
_refine_diff_density_min           -0.249
_refine_diff_density_rms           0.053
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.864
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       236
_refine_ls_number_reflns           3380
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.3127
_refine_ls_R_factor_gt             0.0936
_refine_ls_restrained_S_all        0.864
_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)+(0.0372P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1407
_refine_ls_wR_factor_ref           0.1926
_refine_special_details
;
 Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.77(7)
 0.23(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_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
 O1 O -0.2674(9) 0.2136(3) 0.2142(4) 0.135(2) Uani 1 1 d . . . . .
 O2 O 0.0616(8) 0.2079(2) 0.0880(3) 0.0849(14) Uani 1 1 d . . . . .
 O3 O 0.5210(6) 0.03087(16) 0.2159(3) 0.0700(12) Uani 1 1 d . . . . .
 P1 P 0.2766(3) 0.02145(8) 0.23701(11) 0.0595(5) Uani 1 1 d . . . . .
 C1 C -0.1920(12) 0.1656(4) 0.1932(5) 0.092(2) Uani 1 1 d . . . . .
 H1 H -0.251558 0.132433 0.218383 0.111 Uiso 1 1 calc R U . . .
 C2 C -0.0155(11) 0.1569(3) 0.1314(5) 0.0714(19) Uani 1 1 d . . . . .
 C3 C 0.0953(10) 0.1069(3) 0.1077(4) 0.0618(18) Uani 1 1 d . . . . .
 C4 C 0.2562(11) 0.1255(3) 0.0468(4) 0.0654(18) Uani 1 1 d . . . . .
 C5 C 0.2265(12) 0.1866(4) 0.0359(5) 0.079(2) Uani 1 1 d . . . . .
 C6 C 0.3566(15) 0.2223(4) -0.0194(6) 0.101(3) Uani 1 1 d . . . . .
 H6 H 0.334824 0.262471 -0.024012 0.121 Uiso 1 1 calc R U . . .
 C7 C 0.5166(15) 0.1937(5) -0.0655(5) 0.104(3) Uani 1 1 d . . . . .
 H7 H 0.600004 0.215015 -0.104119 0.125 Uiso 1 1 calc R U . . .
 C8 C 0.5558(13) 0.1327(5) -0.0551(5) 0.095(2) Uani 1 1 d . . . . .
 H8 H 0.669579 0.115354 -0.084748 0.114 Uiso 1 1 calc R U . . .
 C9 C 0.4238(12) 0.0970(3) 0.0004(5) 0.080(2) Uani 1 1 d . . . . .
 H9 H 0.447547 0.056864 0.005592 0.096 Uiso 1 1 calc R U . . .
 C10 C 0.0547(9) 0.0441(3) 0.1390(4) 0.0618(17) Uani 1 1 d . . . . .
 H10A H 0.060080 0.017649 0.087446 0.074 Uiso 1 1 calc R U . . .
 H10B H -0.096999 0.041386 0.158497 0.074 Uiso 1 1 calc R U . . .
 C11 C 0.2123(11) -0.0556(3) 0.2587(4) 0.0638(17) Uani 1 1 d . . . . .
 C12 C 0.3960(10) -0.0906(3) 0.3029(4) 0.073(2) Uani 1 1 d . . . . .
 H12 H 0.536586 -0.073390 0.324099 0.088 Uiso 1 1 calc R U . . .
 C13 C 0.3646(12) -0.1512(3) 0.3144(5) 0.082(2) Uani 1 1 d . . . . .
 H13 H 0.485297 -0.173983 0.342413 0.098 Uiso 1 1 calc R U . . .
 C14 C 0.1534(12) -0.1771(3) 0.2840(5) 0.077(2) Uani 1 1 d . . . . .
 H14 H 0.134031 -0.217046 0.291918 0.092 Uiso 1 1 calc R U . . .
 C15 C -0.0287(11) -0.1437(3) 0.2419(5) 0.082(2) Uani 1 1 d . . . . .
 H15 H -0.169452 -0.161323 0.222310 0.098 Uiso 1 1 calc R U . . .
 C16 C 0.0000(11) -0.0830(3) 0.2289(4) 0.0706(19) Uani 1 1 d . . . . .
 H16 H -0.122101 -0.060955 0.200471 0.085 Uiso 1 1 calc R U . . .
 C17 C 0.2136(11) 0.0639(3) 0.3378(4) 0.0649(18) Uani 1 1 d . . . . .
 C18 C 0.0338(12) 0.0513(3) 0.3869(5) 0.094(2) Uani 1 1 d . . . . .
 H18 H -0.060817 0.019635 0.368995 0.112 Uiso 1 1 calc R U . . .
 C19 C -0.0117(15) 0.0853(4) 0.4638(6) 0.107(3) Uani 1 1 d . . . . .
 H19 H -0.134410 0.075997 0.495651 0.128 Uiso 1 1 calc R U . . .
 C20 C 0.1301(17) 0.1329(4) 0.4911(6) 0.110(3) Uani 1 1 d . . . . .
 H20 H 0.104769 0.154682 0.542648 0.132 Uiso 1 1 calc R U . . .
 C21 C 0.3070(15) 0.1475(4) 0.4421(7) 0.131(4) Uani 1 1 d . . . . .
 H21 H 0.397994 0.180046 0.458879 0.157 Uiso 1 1 calc R U . . .
 C22 C 0.3496(12) 0.1127(4) 0.3658(6) 0.107(3) Uani 1 1 d . . . . .
 H22 H 0.470901 0.122478 0.333394 0.128 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
 O1 C1 1.237(7) . ?
 O2 C2 1.427(7) . ?
 O2 C5 1.392(7) . ?
 O3 P1 1.519(4) . ?
 P1 C10 1.880(5) . ?
 P1 C11 1.839(6) . ?
 P1 C17 1.839(6) . ?
 C1 H1 0.9300 . ?
 C1 C2 1.471(8) . ?
 C2 C3 1.381(8) . ?
 C3 C4 1.441(8) . ?
 C3 C10 1.534(7) . ?
 C4 C5 1.414(8) . ?
 C4 C9 1.421(8) . ?
 C5 C6 1.433(9) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.385(9) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.418(9) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.443(9) . ?
 C9 H9 0.9300 . ?
 C10 H10A 0.9700 . ?
 C10 H10B 0.9700 . ?
 C11 C12 1.428(7) . ?
 C11 C16 1.412(8) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.412(8) . ?
 C13 H13 0.9300 . ?
 C13 C14 1.393(8) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.390(8) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.414(8) . ?
 C16 H16 0.9300 . ?
 C17 C18 1.378(7) . ?
 C17 C22 1.403(8) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.418(9) . ?
 C19 H19 0.9300 . ?
 C19 C20 1.396(10) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.375(10) . ?
 C21 H21 0.9300 . ?
 C21 C22 1.418(9) . ?
 C22 H22 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
 C5 O2 C2 103.8(5) . . ?
 O3 P1 C10 112.7(2) . . ?
 O3 P1 C11 113.0(3) . . ?
 O3 P1 C17 112.2(3) . . ?
 C11 P1 C10 105.0(3) . . ?
 C11 P1 C17 107.5(3) . . ?
 C17 P1 C10 105.9(3) . . ?
 O1 C1 H1 117.5 . . ?
 O1 C1 C2 125.0(8) . . ?
 C2 C1 H1 117.5 . . ?
 O2 C2 C1 116.7(6) . . ?
 C3 C2 O2 112.3(6) . . ?
 C3 C2 C1 131.0(7) . . ?
 C2 C3 C4 106.0(6) . . ?
 C2 C3 C10 127.2(6) . . ?
 C4 C3 C10 126.9(6) . . ?
 C5 C4 C3 106.3(6) . . ?
 C5 C4 C9 118.9(7) . . ?
 C9 C4 C3 134.8(7) . . ?
 O2 C5 C4 111.6(6) . . ?
 O2 C5 C6 124.4(8) . . ?
 C4 C5 C6 123.9(7) . . ?
 C5 C6 H6 121.7 . . ?
 C7 C6 C5 116.6(8) . . ?
 C7 C6 H6 121.7 . . ?
 C6 C7 H7 119.3 . . ?
 C6 C7 C8 121.4(7) . . ?
 C8 C7 H7 119.3 . . ?
 C7 C8 H8 119.1 . . ?
 C7 C8 C9 121.7(7) . . ?
 C9 C8 H8 119.1 . . ?
 C4 C9 C8 117.4(7) . . ?
 C4 C9 H9 121.3 . . ?
 C8 C9 H9 121.3 . . ?
 P1 C10 H10A 109.3 . . ?
 P1 C10 H10B 109.3 . . ?
 C3 C10 P1 111.5(4) . . ?
 C3 C10 H10A 109.3 . . ?
 C3 C10 H10B 109.3 . . ?
 H10A C10 H10B 108.0 . . ?
 C12 C11 P1 117.1(5) . . ?
 C16 C11 P1 124.4(5) . . ?
 C16 C11 C12 118.4(6) . . ?
 C11 C12 H12 120.0 . . ?
 C13 C12 C11 120.1(6) . . ?
 C13 C12 H12 120.0 . . ?
 C12 C13 H13 119.9 . . ?
 C14 C13 C12 120.2(6) . . ?
 C14 C13 H13 119.9 . . ?
 C13 C14 H14 119.7 . . ?
 C15 C14 C13 120.6(6) . . ?
 C15 C14 H14 119.7 . . ?
 C14 C15 H15 120.0 . . ?
 C14 C15 C16 120.0(6) . . ?
 C16 C15 H15 120.0 . . ?
 C11 C16 C15 120.7(6) . . ?
 C11 C16 H16 119.7 . . ?
 C15 C16 H16 119.7 . . ?
 C18 C17 P1 123.5(6) . . ?
 C18 C17 C22 117.3(6) . . ?
 C22 C17 P1 119.2(5) . . ?
 C17 C18 H18 119.0 . . ?
 C17 C18 C19 122.1(7) . . ?
 C19 C18 H18 119.0 . . ?
 C18 C19 H19 120.4 . . ?
 C20 C19 C18 119.2(8) . . ?
 C20 C19 H19 120.4 . . ?
 C19 C20 H20 119.9 . . ?
 C21 C20 C19 120.2(8) . . ?
 C21 C20 H20 119.9 . . ?
 C20 C21 H21 120.2 . . ?
 C20 C21 C22 119.5(8) . . ?
 C22 C21 H21 120.2 . . ?
 C17 C22 C21 121.7(7) . . ?
 C17 C22 H22 119.2 . . ?
 C21 C22 H22 119.2 . . ?

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
 O1 C1 C2 O2 -4.5(11) . . . . ?
 O1 C1 C2 C3 174.6(7) . . . . ?
 O2 C2 C3 C4 0.9(7) . . . . ?
 O2 C2 C3 C10 -178.7(5) . . . . ?
 O2 C5 C6 C7 178.9(7) . . . . ?
 O3 P1 C10 C3 -52.6(5) . . . . ?
 O3 P1 C11 C12 33.5(6) . . . . ?
 O3 P1 C11 C16 -141.9(5) . . . . ?
 O3 P1 C17 C18 -161.0(5) . . . . ?
 O3 P1 C17 C22 20.9(7) . . . . ?
 P1 C11 C12 C13 -174.5(5) . . . . ?
 P1 C11 C16 C15 174.8(5) . . . . ?
 P1 C17 C18 C19 -179.3(5) . . . . ?
 P1 C17 C22 C21 179.0(6) . . . . ?
 C1 C2 C3 C4 -178.2(7) . . . . ?
 C1 C2 C3 C10 2.2(11) . . . . ?
 C2 O2 C5 C4 -1.1(7) . . . . ?
 C2 O2 C5 C6 -178.9(6) . . . . ?
 C2 C3 C4 C5 -1.5(7) . . . . ?
 C2 C3 C4 C9 178.1(7) . . . . ?
 C2 C3 C10 P1 -99.2(6) . . . . ?
 C3 C4 C5 O2 1.6(7) . . . . ?
 C3 C4 C5 C6 179.5(6) . . . . ?
 C3 C4 C9 C8 -179.2(6) . . . . ?
 C4 C3 C10 P1 81.3(6) . . . . ?
 C4 C5 C6 C7 1.4(11) . . . . ?
 C5 O2 C2 C1 179.3(6) . . . . ?
 C5 O2 C2 C3 0.1(7) . . . . ?
 C5 C4 C9 C8 0.4(9) . . . . ?
 C5 C6 C7 C8 -2.7(12) . . . . ?
 C6 C7 C8 C9 3.0(12) . . . . ?
 C7 C8 C9 C4 -1.8(10) . . . . ?
 C9 C4 C5 O2 -178.1(5) . . . . ?
 C9 C4 C5 C6 -0.3(10) . . . . ?
 C10 P1 C11 C12 156.7(5) . . . . ?
 C10 P1 C11 C16 -18.7(6) . . . . ?
 C10 P1 C17 C18 75.6(6) . . . . ?
 C10 P1 C17 C22 -102.4(6) . . . . ?
 C10 C3 C4 C5 178.1(5) . . . . ?
 C10 C3 C4 C9 -2.2(11) . . . . ?
 C11 P1 C10 C3 -176.0(4) . . . . ?
 C11 P1 C17 C18 -36.2(6) . . . . ?
 C11 P1 C17 C22 145.7(6) . . . . ?
 C11 C12 C13 C14 -0.9(10) . . . . ?
 C12 C11 C16 C15 -0.6(9) . . . . ?
 C12 C13 C14 C15 0.1(10) . . . . ?
 C13 C14 C15 C16 0.5(10) . . . . ?
 C14 C15 C16 C11 -0.3(10) . . . . ?
 C16 C11 C12 C13 1.2(9) . . . . ?
 C17 P1 C10 C3 70.4(5) . . . . ?
 C17 P1 C11 C12 -90.9(5) . . . . ?
 C17 P1 C11 C16 93.7(6) . . . . ?
 C17 C18 C19 C20 -0.2(12) . . . . ?
 C18 C17 C22 C21 0.9(12) . . . . ?
 C18 C19 C20 C21 2.0(13) . . . . ?
 C19 C20 C21 C22 -2.4(13) . . . . ?
 C20 C21 C22 C17 0.9(14) . . . . ?
 C22 C17 C18 C19 -1.2(11) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.77(7)
 2 0.23(7)

