data_mo_ydg_lcf_10_0ma_a
_audit_creation_date               2022-12-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_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           'C13 H17 F N6 O3'
_chemical_formula_sum              'C13 H17 F N6 O3'
_chemical_formula_weight           324.32
_chemical_absolute_configuration   .
_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'
 'F' 'F' 0.0171 0.0103 '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'

_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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'

_cell_length_a                     7.9695(6)
_cell_length_b                     12.4446(12)
_cell_length_c                     14.9827(13)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1485.9(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7358
_cell_measurement_temperature      303(2)
_cell_measurement_theta_max        24.343
_cell_measurement_theta_min        2.719
_shelx_estimated_absorpt_T_max     0.971
_shelx_estimated_absorpt_T_min     0.952
_exptl_absorpt_coefficient_mu      0.115
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6741
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.9041.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellowish yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     yellowish
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.450
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               680
_exptl_crystal_size_max            0.43
_exptl_crystal_size_mid            0.4
_exptl_crystal_size_min            0.26
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0564
_diffrn_reflns_av_unetI/netI       0.0360
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         16
_diffrn_reflns_limit_k_min         -16
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              24498
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.563
_diffrn_reflns_theta_min           2.127
_diffrn_ambient_temperature        303.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.000
_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             1.4
_diffrn_source_power               0.07
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.736
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.996
_reflns_number_gt                  2779
_reflns_number_total               3431
_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 1.3 (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      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.170
_refine_diff_density_min           -0.277
_refine_diff_density_rms           0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1026 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.3(4)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       210
_refine_ls_number_reflns           3431
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0559
_refine_ls_R_factor_gt             0.0389
_refine_ls_restrained_S_all        1.042
_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)+(0.0569P)²+0.0608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0886
_refine_ls_wR_factor_ref           0.0961
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8A), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C12(H12A,H12B)
2.c X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N7(H7A,H7B)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_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
 N9 N -0.7665(3) -0.2453(2) -1.00501(15) 0.0401(5) Uani 1 1 d . . . . .
 H9A H -0.837135 -0.211617 -1.038161 0.048 Uiso 1 1 calc R U . . .
 H9B H -0.673637 -0.268122 -1.027290 0.048 Uiso 1 1 calc R U . . .
 O1 O -0.7740(2) -0.48333(13) -0.62566(11) 0.0350(4) Uani 1 1 d . . . . .
 N2 N -0.6212(2) -0.38973(16) -0.73347(13) 0.0293(4) Uani 1 1 d . . . . .
 N3 N -0.8961(2) -0.30133(15) -0.74126(13) 0.0295(4) Uani 1 1 d . . . . .
 O4 O -1.0891(2) -0.37169(16) -0.60122(12) 0.0428(5) Uani 1 1 d . . . . .
 H4 H -1.021460 -0.359956 -0.641307 0.064 Uiso 1 1 calc R U . . .
 N5 N -0.5296(2) -0.35624(16) -0.87242(13) 0.0303(4) Uani 1 1 d . . . . .
 N6 N -0.9477(2) -0.22544(16) -0.88677(12) 0.0293(4) Uani 1 1 d . . . . .
 F7 F -0.4727(2) -0.40710(18) -0.50891(11) 0.0656(6) Uani 1 1 d . . . . .
 O8 O -0.7477(3) -0.31280(16) -0.43469(12) 0.0487(5) Uani 1 1 d . . . . .
 H8 H -0.700907 -0.254667 -0.427985 0.073 Uiso 1 1 calc R U . . .
 C1 C -1.0212(4) -0.4481(2) -0.54126(18) 0.0435(6) Uani 1 1 d . . . . .
 H1A H -1.060200 -0.519102 -0.558203 0.052 Uiso 1 1 calc R U . . .
 H1B H -1.063133 -0.433242 -0.481748 0.052 Uiso 1 1 calc R U . . .
 C2 C -0.8329(3) -0.4485(2) -0.53894(16) 0.0358(6) Uani 1 1 d . . . . .
 H2 H -0.793819 -0.498738 -0.493061 0.043 Uiso 1 1 calc R U . . .
 C3 C -0.6163(3) -0.4358(2) -0.64412(16) 0.0336(5) Uani 1 1 d . . . . .
 H3 H -0.530660 -0.492284 -0.643080 0.040 Uiso 1 1 calc R U . . .
 C4 C -0.7495(3) -0.33495(17) -0.77574(15) 0.0259(5) Uani 1 1 d . . . . .
 C5 C -0.9842(3) -0.24340(18) -0.80029(15) 0.0281(5) Uani 1 1 d . . . . .
 N7 N -1.1285(2) -0.19729(18) -0.77095(15) 0.0422(5) Uani 1 1 d . . . . .
 H7A H -1.159822 -0.205916 -0.716489 0.051 Uiso 1 1 calc R U . . .
 H7B H -1.188572 -0.159484 -0.806837 0.051 Uiso 1 1 calc R U . . .
 C7 C -0.7488(3) -0.3398(2) -0.52568(16) 0.0348(6) Uani 1 1 d . . . . .
 H7 H -0.810946 -0.284967 -0.558977 0.042 Uiso 1 1 calc R U . . .
 C8 C -0.5793(3) -0.3570(2) -0.56909(16) 0.0398(6) Uani 1 1 d . . . . .
 H8A H -0.531755 -0.289658 -0.591618 0.048 Uiso 1 1 calc R U . . .
 C9 C -0.4910(3) -0.39839(19) -0.79557(14) 0.0294(5) Uani 1 1 d . . . . .
 C10 C -0.3327(3) -0.4500(2) -0.77000(18) 0.0374(6) Uani 1 1 d . . . . .
 H10 H -0.280899 -0.423187 -0.715011 0.045 Uiso 1 1 calc R U . . .
 C11 C -0.3135(4) -0.5679(2) -0.7870(3) 0.0647(9) Uani 1 1 d . . . . .
 H11A H -0.254945 -0.610333 -0.742589 0.078 Uiso 1 1 calc R U . . .
 H11B H -0.404766 -0.604738 -0.817027 0.078 Uiso 1 1 calc R U . . .
 C12 C -0.2146(3) -0.4896(3) -0.8393(2) 0.0487(7) Uani 1 1 d . . . . .
 H12A H -0.245153 -0.478899 -0.901356 0.058 Uiso 1 1 calc R U . . .
 H12B H -0.095406 -0.484491 -0.826956 0.058 Uiso 1 1 calc R U . . .
 C13 C -0.6916(3) -0.31658(18) -0.86098(14) 0.0264(5) Uani 1 1 d . . . . .
 C14 C -0.8008(3) -0.26225(18) -0.91955(15) 0.0280(5) Uani 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
 N9 H9A 0.8600 . ?
 N9 H9B 0.8600 . ?
 N9 C14 1.326(3) . ?
 O1 C2 1.448(3) . ?
 O1 C3 1.417(3) . ?
 N2 C3 1.457(3) . ?
 N2 C4 1.383(3) . ?
 N2 C9 1.398(3) . ?
 N3 C4 1.344(3) . ?
 N3 C5 1.340(3) . ?
 O4 H4 0.8200 . ?
 O4 C1 1.416(3) . ?
 N5 C9 1.302(3) . ?
 N5 C13 1.393(3) . ?
 N6 C5 1.347(3) . ?
 N6 C14 1.349(3) . ?
 F7 C8 1.386(3) . ?
 O8 H8 0.8200 . ?
 O8 C7 1.404(3) . ?
 C1 H1A 0.9700 . ?
 C1 H1B 0.9700 . ?
 C1 C2 1.502(4) . ?
 C2 H2 0.9800 . ?
 C2 C7 1.522(3) . ?
 C3 H3 0.9800 . ?
 C3 C8 1.520(4) . ?
 C4 C13 1.377(3) . ?
 C5 N7 1.358(3) . ?
 N7 H7A 0.8600 . ?
 N7 H7B 0.8600 . ?
 C7 H7 0.9800 . ?
 C7 C8 1.515(4) . ?
 C8 H8A 0.9800 . ?
 C9 C10 1.466(3) . ?
 C10 H10 0.9800 . ?
 C10 C11 1.497(4) . ?
 C10 C12 1.486(4) . ?
 C11 H11A 0.9700 . ?
 C11 H11B 0.9700 . ?
 C11 C12 1.478(5) . ?
 C12 H12A 0.9700 . ?
 C12 H12B 0.9700 . ?
 C13 C14 1.409(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
 H9A N9 H9B 120.0 . . ?
 C14 N9 H9A 120.0 . . ?
 C14 N9 H9B 120.0 . . ?
 C3 O1 C2 109.72(18) . . ?
 C4 N2 C3 129.39(19) . . ?
 C4 N2 C9 106.39(18) . . ?
 C9 N2 C3 124.17(18) . . ?
 C5 N3 C4 111.67(19) . . ?
 C1 O4 H4 109.5 . . ?
 C9 N5 C13 104.65(19) . . ?
 C5 N6 C14 118.77(19) . . ?
 C7 O8 H8 109.5 . . ?
 O4 C1 H1A 108.9 . . ?
 O4 C1 H1B 108.9 . . ?
 O4 C1 C2 113.5(2) . . ?
 H1A C1 H1B 107.7 . . ?
 C2 C1 H1A 108.9 . . ?
 C2 C1 H1B 108.9 . . ?
 O1 C2 C1 107.7(2) . . ?
 O1 C2 H2 109.6 . . ?
 O1 C2 C7 103.93(18) . . ?
 C1 C2 H2 109.6 . . ?
 C1 C2 C7 116.1(2) . . ?
 C7 C2 H2 109.6 . . ?
 O1 C3 N2 108.68(18) . . ?
 O1 C3 H3 108.4 . . ?
 O1 C3 C8 107.29(19) . . ?
 N2 C3 H3 108.4 . . ?
 N2 C3 C8 115.5(2) . . ?
 C8 C3 H3 108.4 . . ?
 N3 C4 N2 128.3(2) . . ?
 N3 C4 C13 126.6(2) . . ?
 C13 C4 N2 105.02(19) . . ?
 N3 C5 N6 127.7(2) . . ?
 N3 C5 N7 117.2(2) . . ?
 N6 C5 N7 115.1(2) . . ?
 C5 N7 H7A 120.0 . . ?
 C5 N7 H7B 120.0 . . ?
 H7A N7 H7B 120.0 . . ?
 O8 C7 C2 110.0(2) . . ?
 O8 C7 H7 109.3 . . ?
 O8 C7 C8 116.4(2) . . ?
 C2 C7 H7 109.3 . . ?
 C8 C7 C2 102.2(2) . . ?
 C8 C7 H7 109.3 . . ?
 F7 C8 C3 108.1(2) . . ?
 F7 C8 C7 109.3(2) . . ?
 F7 C8 H8A 111.8 . . ?
 C3 C8 H8A 111.8 . . ?
 C7 C8 C3 103.61(19) . . ?
 C7 C8 H8A 111.8 . . ?
 N2 C9 C10 119.89(19) . . ?
 N5 C9 N2 112.5(2) . . ?
 N5 C9 C10 127.6(2) . . ?
 C9 C10 H10 115.7 . . ?
 C9 C10 C11 118.2(3) . . ?
 C9 C10 C12 120.5(2) . . ?
 C11 C10 H10 115.7 . . ?
 C12 C10 H10 115.7 . . ?
 C12 C10 C11 59.4(2) . . ?
 C10 C11 H11A 117.8 . . ?
 C10 C11 H11B 117.8 . . ?
 H11A C11 H11B 114.9 . . ?
 C12 C11 C10 59.9(2) . . ?
 C12 C11 H11A 117.8 . . ?
 C12 C11 H11B 117.8 . . ?
 C10 C12 H12A 117.7 . . ?
 C10 C12 H12B 117.7 . . ?
 C11 C12 C10 60.7(2) . . ?
 C11 C12 H12A 117.7 . . ?
 C11 C12 H12B 117.7 . . ?
 H12A C12 H12B 114.8 . . ?
 N5 C13 C14 131.8(2) . . ?
 C4 C13 N5 111.45(19) . . ?
 C4 C13 C14 116.8(2) . . ?
 N9 C14 N6 118.5(2) . . ?
 N9 C14 C13 123.4(2) . . ?
 N6 C14 C13 118.2(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 C2 C7 O8 -160.3(2) . . . . ?
 O1 C2 C7 C8 -36.0(2) . . . . ?
 O1 C3 C8 F7 98.7(2) . . . . ?
 O1 C3 C8 C7 -17.2(2) . . . . ?
 N2 C3 C8 F7 -140.0(2) . . . . ?
 N2 C3 C8 C7 104.1(2) . . . . ?
 N2 C4 C13 N5 -1.3(3) . . . . ?
 N2 C4 C13 C14 179.2(2) . . . . ?
 N2 C9 C10 C11 92.2(3) . . . . ?
 N2 C9 C10 C12 161.4(2) . . . . ?
 N3 C4 C13 N5 175.7(2) . . . . ?
 N3 C4 C13 C14 -3.8(3) . . . . ?
 O4 C1 C2 O1 -65.3(3) . . . . ?
 O4 C1 C2 C7 50.7(3) . . . . ?
 N5 C9 C10 C11 -88.3(3) . . . . ?
 N5 C9 C10 C12 -19.1(4) . . . . ?
 N5 C13 C14 N9 5.3(4) . . . . ?
 N5 C13 C14 N6 -174.6(2) . . . . ?
 O8 C7 C8 F7 37.0(3) . . . . ?
 O8 C7 C8 C3 152.1(2) . . . . ?
 C1 C2 C7 O8 81.6(3) . . . . ?
 C1 C2 C7 C8 -154.1(2) . . . . ?
 C2 O1 C3 N2 -131.4(2) . . . . ?
 C2 O1 C3 C8 -5.9(2) . . . . ?
 C2 C7 C8 F7 -82.9(2) . . . . ?
 C2 C7 C8 C3 32.1(2) . . . . ?
 C3 O1 C2 C1 150.3(2) . . . . ?
 C3 O1 C2 C7 26.5(2) . . . . ?
 C3 N2 C4 N3 7.3(4) . . . . ?
 C3 N2 C4 C13 -175.7(2) . . . . ?
 C3 N2 C9 N5 176.0(2) . . . . ?
 C3 N2 C9 C10 -4.5(3) . . . . ?
 C4 N2 C3 O1 39.6(3) . . . . ?
 C4 N2 C3 C8 -81.0(3) . . . . ?
 C4 N2 C9 N5 -1.5(3) . . . . ?
 C4 N2 C9 C10 178.0(2) . . . . ?
 C4 N3 C5 N6 5.9(3) . . . . ?
 C4 N3 C5 N7 -174.7(2) . . . . ?
 C4 C13 C14 N9 -175.4(2) . . . . ?
 C4 C13 C14 N6 4.7(3) . . . . ?
 C5 N3 C4 N2 175.1(2) . . . . ?
 C5 N3 C4 C13 -1.2(3) . . . . ?
 C5 N6 C14 N9 179.2(2) . . . . ?
 C5 N6 C14 C13 -0.9(3) . . . . ?
 C9 N2 C3 O1 -137.4(2) . . . . ?
 C9 N2 C3 C8 102.0(3) . . . . ?
 C9 N2 C4 N3 -175.3(2) . . . . ?
 C9 N2 C4 C13 1.7(2) . . . . ?
 C9 N5 C13 C4 0.4(3) . . . . ?
 C9 N5 C13 C14 179.8(2) . . . . ?
 C9 C10 C11 C12 110.6(3) . . . . ?
 C9 C10 C12 C11 -106.8(3) . . . . ?
 C13 N5 C9 N2 0.7(3) . . . . ?
 C13 N5 C9 C10 -178.8(2) . . . . ?
 C14 N6 C5 N3 -5.0(3) . . . . ?
 C14 N6 C5 N7 175.5(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
