#------------------------------------------------------------------------------
#$Date: 2022-08-14 01:29:14 +0300 (Sun, 14 Aug 2022) $
#$Revision: 277241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245310.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245310
loop_
_publ_author_name
'Chen, Xiaofeng'
'Ning, Lifeng'
_publ_section_title
;
 Pharmaceutical cocrystals of nomegestrol acetate with superior
 dissolution
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00870J
_journal_year                    2022
_chemical_formula_moiety         'C23 H30 O4, C7 H6 O4'
_chemical_formula_sum            'C30 H36 O8'
_chemical_formula_weight         524.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.141(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8459(7)
_cell_length_b                   11.2095(7)
_cell_length_c                   11.9727(8)
_cell_measurement_reflns_used    5793
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.363
_cell_measurement_theta_min      2.604
_cell_volume                     1328.30(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_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_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14222
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.058
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1758 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8766. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.7(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4933
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0411
_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)+(0.0385P)²+0.2467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                4195
_reflns_number_total             4933
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00870j1.cif
_cod_data_source_block           mo_20211126_0m
_cod_database_code               7245310
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.3(13)
 0.7(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O7-H7A = O5-H5 = O8-H8A
 0.84 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C27(H27), C29(H29), C30(H30)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.4479(2) 0.6103(3) 1.62485(19) 0.0473(6) Uani 1 1 d . . . . .
O2 O -0.2421(2) 0.6369(2) 0.5580(2) 0.0467(6) Uani 1 1 d . . . . .
O3 O 0.01105(19) 0.43663(19) 0.73408(16) 0.0276(5) Uani 1 1 d . . . . .
O4 O -0.0533(2) 0.4244(2) 0.53120(19) 0.0483(7) Uani 1 1 d . . . . .
C1 C 0.1730(3) 0.5146(3) 1.3409(3) 0.0376(8) Uani 1 1 d . . . . .
H1A H 0.075739 0.496288 1.313903 0.045 Uiso 1 1 calc R . . . .
H1B H 0.219808 0.440062 1.336483 0.045 Uiso 1 1 calc R . . . .
C2 C 0.2301(3) 0.5593(4) 1.4729(3) 0.0422(9) Uani 1 1 d . . . . .
H2A H 0.172517 0.624936 1.479870 0.051 Uiso 1 1 calc R . . . .
H2B H 0.227313 0.493755 1.527277 0.051 Uiso 1 1 calc R . . . .
C3 C 0.3716(3) 0.6028(3) 1.5144(3) 0.0344(7) Uani 1 1 d . . . . .
C4 C 0.4185(3) 0.6407(3) 1.4233(3) 0.0320(7) Uani 1 1 d . . . . .
H4 H 0.510457 0.663402 1.449657 0.038 Uiso 1 1 calc R . . . .
C5 C 0.3383(3) 0.6455(3) 1.3026(3) 0.0260(6) Uani 1 1 d . . . . .
C6 C 0.3906(3) 0.6914(3) 1.2160(3) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.3076(3) 0.7038(3) 1.0981(3) 0.0285(7) Uani 1 1 d . . . . .
H7 H 0.343246 0.738342 1.045089 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1623(3) 0.6669(3) 1.0437(2) 0.0245(6) Uani 1 1 d . . . . .
H8 H 0.106343 0.737517 1.044363 0.029 Uiso 1 1 calc R . . . .
C9 C 0.1378(3) 0.5679(3) 1.1208(2) 0.0240(6) Uani 1 1 d . . . . .
H9 H 0.192039 0.496964 1.117358 0.029 Uiso 1 1 calc R . . . .
C10 C 0.1908(3) 0.6080(3) 1.2549(2) 0.0274(7) Uani 1 1 d . . . . .
H10 H 0.137691 0.679998 1.257702 0.033 Uiso 1 1 calc R . . . .
C11 C -0.0117(3) 0.5306(3) 1.0655(2) 0.0277(7) Uani 1 1 d . . . . .
H11A H -0.067346 0.598264 1.071543 0.033 Uiso 1 1 calc R . . . .
H11B H -0.024196 0.463537 1.113674 0.033 Uiso 1 1 calc R . . . .
C12 C -0.0613(3) 0.4924(3) 0.9305(2) 0.0267(6) Uani 1 1 d . . . . .
H12A H -0.013816 0.418603 0.925209 0.032 Uiso 1 1 calc R . . . .
H12B H -0.159238 0.474733 0.897479 0.032 Uiso 1 1 calc R . . . .
C13 C -0.0357(3) 0.5907(3) 0.8525(2) 0.0247(6) Uani 1 1 d . . . . .
C14 C 0.1153(3) 0.6237(3) 0.9118(2) 0.0234(6) Uani 1 1 d . . . . .
H14 H 0.166259 0.548494 0.915091 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1353(3) 0.7037(3) 0.8173(2) 0.0288(7) Uani 1 1 d . . . . .
H15A H 0.230455 0.702113 0.827054 0.035 Uiso 1 1 calc R . . . .
H15B H 0.109346 0.787086 0.824412 0.035 Uiso 1 1 calc R . . . .
C16 C 0.0403(3) 0.6483(3) 0.6936(3) 0.0325(7) Uani 1 1 d . . . . .
H16A H -0.016131 0.710972 0.637841 0.039 Uiso 1 1 calc R . . . .
H16B H 0.093667 0.608562 0.654158 0.039 Uiso 1 1 calc R . . . .
C17 C -0.0495(3) 0.5567(3) 0.7213(2) 0.0269(6) Uani 1 1 d . . . . .
C18 C -0.1290(3) 0.6979(3) 0.8406(3) 0.0333(7) Uani 1 1 d . . . . .
H18A H -0.107341 0.732343 0.921743 0.050 Uiso 1 1 calc GR . . . .
H18B H -0.223375 0.671388 0.805210 0.050 Uiso 1 1 calc GR . . . .
H18C H -0.115782 0.758330 0.787369 0.050 Uiso 1 1 calc GR . . . .
C20 C -0.1964(3) 0.5533(3) 0.6259(3) 0.0328(7) Uani 1 1 d . . . . .
C21 C -0.2835(3) 0.4493(3) 0.6275(3) 0.0392(8) Uani 1 1 d . . . . .
H21A H -0.333767 0.469748 0.676745 0.059 Uiso 1 1 calc GR . . . .
H21B H -0.226325 0.379641 0.663067 0.059 Uiso 1 1 calc GR . . . .
H21C H -0.347239 0.430894 0.543617 0.059 Uiso 1 1 calc GR . . . .
C22 C 0.5373(3) 0.7277(3) 1.2631(3) 0.0370(8) Uani 1 1 d . . . . .
H22A H 0.552854 0.797580 1.316329 0.055 Uiso 1 1 calc GR . . . .
H22B H 0.559854 0.747342 1.193940 0.055 Uiso 1 1 calc GR . . . .
H22C H 0.594412 0.661622 1.309745 0.055 Uiso 1 1 calc GR . . . .
C23 C 0.0095(3) 0.3842(3) 0.6331(3) 0.0321(7) Uani 1 1 d . . . . .
C24 C 0.0921(3) 0.2737(3) 0.6604(3) 0.0393(8) Uani 1 1 d . . . . .
H24A H 0.185712 0.293905 0.676250 0.059 Uiso 1 1 calc GR . . . .
H24B H 0.055590 0.219421 0.590187 0.059 Uiso 1 1 calc GR . . . .
H24C H 0.089538 0.234698 0.732666 0.059 Uiso 1 1 calc GR . . . .
H7A H 0.488(5) 0.566(5) -0.226(3) 0.11(2) Uiso 1 1 d D . . . .
O5 O 0.3055(2) 0.3406(3) -0.0049(3) 0.0513(7) Uani 1 1 d D . . . .
H5 H 0.295(5) 0.368(5) -0.079(3) 0.093(18) Uiso 1 1 d D . . . .
O6 O 0.3283(2) 0.4649(2) -0.1807(2) 0.0403(6) Uani 1 1 d . . . . .
O7 O 0.5262(2) 0.5493(3) -0.1476(2) 0.0487(7) Uani 1 1 d D . . . .
O8 O 0.8218(3) 0.4947(3) 0.2859(2) 0.0484(7) Uani 1 1 d D . . . .
H8A H 0.842(5) 0.470(4) 0.358(3) 0.081(16) Uiso 1 1 d D . . . .
C25 C 0.4442(3) 0.4886(3) -0.1101(3) 0.0328(7) Uani 1 1 d . . . . .
C26 C 0.5055(3) 0.4533(3) 0.0187(3) 0.0337(7) Uani 1 1 d . . . . .
C27 C 0.6367(3) 0.4908(3) 0.0954(3) 0.0339(7) Uani 1 1 d . . . . .
H27 H 0.686281 0.539811 0.063564 0.041 Uiso 1 1 calc R . . . .
C28 C 0.6936(4) 0.4568(3) 0.2163(3) 0.0375(8) Uani 1 1 d . . . . .
C29 C 0.6200(4) 0.3853(3) 0.2627(3) 0.0420(8) Uani 1 1 d . . . . .
H29 H 0.659382 0.362110 0.346326 0.050 Uiso 1 1 calc R . . . .
C30 C 0.4907(4) 0.3478(3) 0.1887(3) 0.0441(9) Uani 1 1 d . . . . .
H30 H 0.441410 0.299327 0.221181 0.053 Uiso 1 1 calc R . . . .
C31 C 0.4331(3) 0.3819(3) 0.0657(3) 0.0375(8) Uani 1 1 d . . . . .
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'
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
C23 O3 C17 117.7(2) . . ?
C2 C1 C10 111.2(3) . . ?
C3 C2 C1 112.3(3) . . ?
O1 C3 C2 121.6(3) . . ?
O1 C3 C4 119.8(3) . . ?
C4 C3 C2 118.6(3) . . ?
C5 C4 C3 123.4(3) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 C10 120.6(3) . . ?
C6 C5 C10 118.9(2) . . ?
C5 C6 C22 118.9(2) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 C22 121.3(3) . . ?
C6 C7 C8 124.5(3) . . ?
C7 C8 C9 110.4(2) . . ?
C7 C8 C14 112.6(2) . . ?
C14 C8 C9 109.1(2) . . ?
C8 C9 C10 109.6(2) . . ?
C8 C9 C11 110.5(2) . . ?
C10 C9 C11 114.0(2) . . ?
C1 C10 C9 113.9(2) . . ?
C5 C10 C1 109.8(2) . . ?
C5 C10 C9 111.1(2) . . ?
C9 C11 C12 112.4(2) . . ?
C13 C12 C11 111.4(2) . . ?
C12 C13 C17 117.9(2) . . ?
C14 C13 C12 108.3(2) . . ?
C14 C13 C17 99.7(2) . . ?
C14 C13 C18 112.9(3) . . ?
C18 C13 C12 109.8(2) . . ?
C18 C13 C17 108.0(2) . . ?
C8 C14 C13 113.3(2) . . ?
C8 C14 C15 119.5(2) . . ?
C15 C14 C13 104.3(2) . . ?
C14 C15 C16 103.5(2) . . ?
C17 C16 C15 107.1(2) . . ?
O3 C17 C13 105.2(2) . . ?
O3 C17 C16 109.6(2) . . ?
O3 C17 C20 109.7(2) . . ?
C16 C17 C13 104.1(2) . . ?
C20 C17 C13 113.4(2) . . ?
C20 C17 C16 114.3(2) . . ?
O2 C20 C17 119.8(3) . . ?
O2 C20 C21 121.5(3) . . ?
C21 C20 C17 118.4(3) . . ?
O3 C23 C24 112.6(3) . . ?
O4 C23 O3 122.7(3) . . ?
O4 C23 C24 124.7(3) . . ?
O6 C25 O7 121.1(3) . . ?
O6 C25 C26 124.4(3) . . ?
O7 C25 C26 114.5(3) . . ?
C27 C26 C25 120.7(3) . . ?
C31 C26 C25 119.6(3) . . ?
C31 C26 C27 119.8(3) . . ?
C28 C27 C26 120.2(3) . . ?
O8 C28 C27 117.5(3) . . ?
O8 C28 C29 122.8(3) . . ?
C27 C28 C29 119.7(3) . . ?
C30 C29 C28 120.9(3) . . ?
C29 C30 C31 119.4(3) . . ?
O5 C31 C26 122.6(3) . . ?
O5 C31 C30 117.4(3) . . ?
C26 C31 C30 120.0(3) . . ?
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 C3 1.243(4) . ?
O2 C20 1.206(4) . ?
O3 C17 1.478(4) . ?
O3 C23 1.338(3) . ?
O4 C23 1.215(4) . ?
C1 C2 1.528(4) . ?
C1 C10 1.535(4) . ?
C2 C3 1.489(5) . ?
C3 C4 1.443(4) . ?
C4 C5 1.349(4) . ?
C5 C6 1.464(4) . ?
C5 C10 1.522(4) . ?
C6 C7 1.335(4) . ?
C6 C22 1.510(4) . ?
C7 C8 1.496(4) . ?
C8 C9 1.534(4) . ?
C8 C14 1.526(4) . ?
C9 C10 1.535(4) . ?
C9 C11 1.537(4) . ?
C11 C12 1.542(4) . ?
C12 C13 1.541(4) . ?
C13 C14 1.541(4) . ?
C13 C17 1.563(4) . ?
C13 C18 1.541(4) . ?
C14 C15 1.526(4) . ?
C15 C16 1.547(4) . ?
C16 C17 1.541(4) . ?
C17 C20 1.535(4) . ?
C20 C21 1.505(5) . ?
C23 C24 1.485(5) . ?
O5 C31 1.373(4) . ?
O6 C25 1.223(4) . ?
O7 C25 1.335(4) . ?
O8 C28 1.364(4) . ?
C25 C26 1.462(4) . ?
C26 C27 1.406(5) . ?
C26 C31 1.391(5) . ?
C27 C28 1.376(4) . ?
C28 C29 1.396(5) . ?
C29 C30 1.383(5) . ?
C30 C31 1.398(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O6 0.90(2) 1.77(3) 2.618(4) 155(5) . yes
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.3(13)
2 0.7(13)
