The solid state forms of the sex hormone 17-β-estradiol
Stevenson, Erin L.; Lancaster, Robert W.; Buanz, Asma B. M.; Price, Louise S.; Tocher, Derek A.; Price, Sarah L.; CrystEngComm 21 (2019) 2154–; doi:10.1039/C8CE01874J

data_7231966
_publ_section_title
;
 The solid state forms of the sex hormone 17-\b-estradiol
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2154
_journal_paper_doi               10.1039/C8CE01874J
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C18 H24 O2, C3 H8 O'
_chemical_formula_sum            'C21 H32 O3'
_chemical_formula_weight         332.46
_chemical_name_systematic        'Beta Estradiol Propanol Solvate'
_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             2017-03-05
_audit_creation_method
;
Olex2 1.2
(compiled Mar  2 2017 14:02:25 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-10-25 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.58547(6)
_cell_length_b                   23.9331(3)
_cell_length_c                   12.23603(11)
_cell_measurement_reflns_used    21844
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      73.5030
_cell_measurement_theta_min      4.0180
_cell_volume                     1928.53(3)
_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      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1790767000
_diffrn_orient_matrix_UB_12      -0.0300815000
_diffrn_orient_matrix_UB_13      0.0557037000
_diffrn_orient_matrix_UB_21      -0.1208395000
_diffrn_orient_matrix_UB_22      0.0024052000
_diffrn_orient_matrix_UB_23      -0.1076930000
_diffrn_orient_matrix_UB_31      0.0894946000
_diffrn_orient_matrix_UB_32      -0.0568781000
_diffrn_orient_matrix_UB_33      -0.0339852000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29872
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         3.694
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56810
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method 'Crystalised from anhydrous n-Propanol'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1568 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0650P)^2^+0.2740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3773
_reflns_number_total             3880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01874j2.cif
_cod_data_source_block           xstr0708
_cod_depositor_comments
'Adding full bibliography for 7231965--7231969.cif.'
_cod_database_code               7231966
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C21H32O3
_chemical_oxdiff_usercomment     'Propanol solvate'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C14(H14), C9(H9), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C7(H7A,H7B),
 C16(H16A,H16B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2A), C1(H1A)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              75701
_olex2_date_sample_data_collection 2017-01-30
_olex2_exptl_crystal_mounting_method 'Nylon Loop'
_olex2_submission_original_sample_id 'Beta Estradiol Propanol Solvate ELS113'
_olex2_submission_special_instructions 'No special instructions were received'