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_7231967
_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_absolute_configuration rm
_chemical_formula_moiety         '2(C18 H24 O2)'
_chemical_formula_sum            'C36 H48 O4'
_chemical_formula_weight         544.74
_chemical_name_systematic        'Beta Estradiol Anhydrate'
_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             2017-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_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                   6.41117(7)
_cell_length_b                   12.19725(13)
_cell_length_c                   37.9575(4)
_cell_measurement_reflns_used    25363
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4790
_cell_measurement_theta_min      3.7720
_cell_volume                     2968.23(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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 0.996
_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    -59.00 -10.00   1.00    1.00    --  -42.62 -77.00 -60.00   49
  2  \w    -39.00 -10.00   1.00    1.00    --  -42.62 -77.00-150.00   29
  3  \w      4.00  57.00   1.00    1.00    --   42.62 -99.00-150.00   53
  4  \w     33.00 118.00   1.00    2.50    --  106.36-125.00 -30.00   85
  5  \w     75.00 102.00   1.00    2.50    --  106.36 -94.00-150.00   27
  6  \w     25.00 108.00   1.00    2.50    --  106.36 -94.00   0.00   83
  7  \w     48.00 109.00   1.00    2.50    --  106.36 -94.00  90.00   61
  8  \w     34.00 129.00   1.00    2.50    --  106.36 -61.00 120.00   95
  9  \w     81.00 139.00   1.00    2.50    --  106.36  45.00  30.00   58
 10  \w    106.00 139.00   1.00    2.50    --  106.36  77.00  60.00   33
 11  \w    129.00 156.00   1.00    2.50    --  106.36  57.00 122.50   27
 12  \w     78.00 104.00   1.00    2.50    --  106.36  56.00 147.70   26
 13  \w     76.00 130.00   1.00    2.50    --  106.36  66.00  91.10   54
 14  \w     77.00 103.00   1.00    2.50    --  106.36  61.00  60.00   26
 15  \w     77.00 103.00   1.00    2.50    --  106.36  61.00  30.00   26
 16  \w     76.00 101.00   1.00    2.50    --  106.36  69.00  -7.06   25
 17  \w     79.00 177.00   1.00    2.50    --  106.36  52.00  -7.92   98
 18  \w    138.00 164.00   1.00    2.50    --  106.36  61.00 -90.00   26
 19  \w    130.00 178.00   1.00    2.50    --  106.36  77.00-180.00   48
 20  \w     81.00 108.00   1.00    2.50    --  106.36  61.00-180.00   27
 21  \w     74.00 100.00   1.00    2.50    --  106.36  77.00-180.00   26
 22  \w     78.00 166.00   1.00    2.50    --  106.36  61.00-150.00   88
 23  \w     77.00 104.00   1.00    2.50    --  106.36  61.00 -90.00   27
 24  \w     77.00 176.00   1.00    2.50    --  106.36  60.00 -45.78   99
 25  \w     79.00 105.00   1.00    2.50    --  106.36  55.00 132.65   26
 26  \w     78.00 104.00   1.00    2.50    --  106.36  57.00 122.50   26
 27  \w     77.00 139.00   1.00    2.50    --  106.36  64.00 150.22   62
 28  \w     74.00 100.00   1.00    2.50    --  106.36  77.00  60.00   26
 29  \w     74.00 178.00   1.00    2.50    --  106.36  77.00  90.00  104
 30  \w     74.00 175.00   1.00    2.50    --  106.36  77.00 150.00  101
 31  \w     77.00 103.00   1.00    2.50    --  106.36  61.00 -30.00   26
 32  \w     77.00 156.00   1.00    2.50    --  106.36  61.00 -60.00   79
 33  \w     77.00 103.00   1.00    2.50    --  106.36  61.00-120.00   26
 34  \w     74.00 100.00   1.00    2.50    --  106.36  77.00 -90.00   26
 35  \w     74.00 178.00   1.00    2.50    --  106.36  77.00-120.00  104
 36  \w     74.00 100.00   1.00    2.50    --  106.36  77.00 -30.00   26
 37  \w     74.00 177.00   1.00    2.50    --  106.36  77.00  30.00  103
 38  \w     74.00 100.00   1.00    2.50    --  106.36  77.00-150.00   26
 39  \w     13.00  39.00   1.00    1.00    --   42.62  77.00-180.00   26
 40  \w    -68.00  28.00   1.00    1.00    --  -42.62  57.00 -30.00   96
 41  \w    -66.00 -16.00   1.00    1.00    --  -42.62 -57.00 150.00   50
 42  \w    -66.00 -10.00   1.00    1.00    --  -42.62 -77.00  90.00   56
 43  \w    -69.00 -11.00   1.00    1.00    --  -42.62 -77.00  30.00   58
 44  \w      3.00  76.00   1.00    1.00    --   42.62 -99.00  90.00   73
 45  \w   -110.00 -18.00   1.00    1.00    --  -42.62 -38.00-150.00   92
 46  \w   -117.00 -90.00   1.00    1.00    --  -42.62 -77.00-150.00   27
 47  \w   -119.00  -8.00   1.00    1.00    --  -42.62 -19.00 -60.00  111
 48  \w   -113.00 -73.00   1.00    1.00    --  -42.62 -77.00  90.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0772799000
_diffrn_orient_matrix_UB_12      0.0718110000
_diffrn_orient_matrix_UB_13      0.0307349000
_diffrn_orient_matrix_UB_21      -0.1155026000
_diffrn_orient_matrix_UB_22      0.0994059000
_diffrn_orient_matrix_UB_23      -0.0157067000
_diffrn_orient_matrix_UB_31      -0.1959765000
_diffrn_orient_matrix_UB_32      -0.0302587000
_diffrn_orient_matrix_UB_33      0.0213637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            48838
_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         73.711
_diffrn_reflns_theta_min         3.807
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_recrystallization_method 'Sublimation at 0.04 Torr'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0660P)^2^+0.3320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5742
_reflns_number_total             5932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01874j2.cif
_cod_data_source_block           xstr0716
_cod_depositor_comments
'Adding full bibliography for 7231965--7231969.cif.'
_cod_database_code               7231967
_chemical_oxdiff_formula         C18H24O2
_chemical_oxdiff_usercomment     anhydrous?
_reflns_odcompleteness_completeness 99.94
_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:
 C9(H9), C11(H11), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C19(H19A,H19B), C23(H23A,H23B), C30(H30A,H30B), C31(H31A,
 H31B), C33(H33A,H33B), C34(H34A,H34B), C36(H36A,H36B), C38(H38A,H38B),
 C39(H39A,H39B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C16(H16), C32(H32)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_shelx_res_checksum              71859
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_data_collection 2017-02-09
_olex2_exptl_crystal_mounting_method 'Nylon Loop'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.712