Solid-state characterization of 17β-estradiol co-crystals presenting improved dissolution and bioavailability
Wang, Jian-Rong; Wang, Xiaojuan; Yang, Yong; Chen, Xiaoyan; Mei, Xuefeng; CrystEngComm 18 (2016) 3498–; doi:10.1039/C6CE00433D

data_7224947
_publ_section_title
;
 Solid-state characterization of 17\b-estradiol co-crystals presenting
 improved dissolution and bioavailability
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3498
_journal_paper_doi               10.1039/C6CE00433D
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'H2 O, C18 H24 O2, 0.5(C4 H10 N2)'
_chemical_formula_sum            'C20 H31 N O3'
_chemical_formula_weight         333.46
_chemical_name_systematic        Estradiol
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-01-13 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.038(6)
_cell_angle_beta                 97.853(6)
_cell_angle_gamma                110.152(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3931(7)
_cell_length_b                   9.2277(8)
_cell_length_c                   14.7018(13)
_cell_measurement_reflns_used    3123
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      2.99
_cell_volume                     913.71(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_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            13327
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.400
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0495 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.9390.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(6)
_refine_ls_extinction_coef       0.0043(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         6960
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0430P)^2^+0.0422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.738
_reflns_Friedel_fraction_max     0.674
_reflns_number_gt                4406
_reflns_number_total             6960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00433d2.cif
_cod_data_source_block           1056531
_cod_depositor_comments
;
Adding full bibliography for 7224946--7224947.cif.

2017-03-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        913.72(15)
_cod_original_formula_moiety     '2(H2 O), 2(C18 H24 O2), C4 H10 N2'
_cod_original_formula_sum        'C40 H62 N2 O6'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     666.92
_cod_database_code               7224947
_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, All O(H) groups
2. Restrained distances
 O2S-H2SA = O1S-H1SA = O1S-H1SB
 0.8 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C14(H14), C17(H17), C8'(H8'), C9'(H9'), C14'(H14'), C17'(H17')
3.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), C6'(H6'A,H6'B), C7'(H7'A,H7'B), C11'(H11C,H11D), C12'(H12C,
 H12D), C15'(H15C,H15D), C16'(H16C,H16D), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C1'(H1'), C2'(H2'), C4'(H4')
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O2(H2A), O4(H4A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'