Ethinyl estradiol cocrystals assembled by chain structures: improvement in stability and solubility
Du, Rongkai; Xu, Juan; Zhang, Lei; Ning, Lifeng; Li, Shan; New Journal of Chemistry 43 (2019) 16889–; doi:10.1039/C9NJ04147H

data_7058872
_publ_section_title
;
 Ethinyl estradiol cocrystals assembled by chain structures: improvement
 in stability and solubility
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16889
_journal_paper_doi               10.1039/C9NJ04147H
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H24 O2, C10 H8 N2'
_chemical_formula_sum            'C30 H32 N2 O2'
_chemical_formula_weight         452.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3914(7)
_cell_length_b                   13.6642(8)
_cell_length_c                   19.2618(9)
_cell_measurement_reflns_used    5323
_cell_measurement_temperature    173(6)
_cell_measurement_theta_max      26.2910
_cell_measurement_theta_min      3.6520
_cell_volume                     2471.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      1.00  65.00   1.00    3.17    --   15.65  57.00 -90.00   64
  2  \w    -25.00  41.00   1.00    3.17    --   15.65 -99.00 -30.00   66
  3  \w    -14.00  22.00   1.00    3.17    --  -16.43 -99.00 -30.00   36
  4  \w    -56.00  35.00   1.00    3.17    --   15.65 -19.00 -30.00   91
  5  \w     -3.00  85.00   1.00    3.17    --   15.65  38.00 150.00   88
  6  \w    -25.00  11.00   1.00    3.17    --  -16.43 -99.00 150.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0052511000
_diffrn_orient_matrix_UB_12      -0.0516345000
_diffrn_orient_matrix_UB_13      -0.0025978000
_diffrn_orient_matrix_UB_21      0.0716884000
_diffrn_orient_matrix_UB_22      -0.0023354000
_diffrn_orient_matrix_UB_23      -0.0114594000
_diffrn_orient_matrix_UB_31      0.0232661000
_diffrn_orient_matrix_UB_32      -0.0045801000
_diffrn_orient_matrix_UB_33      0.0349004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20862
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.396
_diffrn_reflns_theta_min         3.506
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0515
_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/[\s^2^(Fo^2^)+(0.0566P)^2^+0.1403P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                4289
_reflns_number_total             5866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj04147h2.cif
_cod_data_source_block           EE-BIP
_cod_depositor_comments
'Adding full bibliography for 7058869--7058873.cif.'
_cod_database_code               7058872
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
 C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e :
 C21(H21)
;
_shelx_res_checksum              7518
_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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.660