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_7231968
_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, C2 H3 N'
_chemical_formula_sum            'C20 H27 N O2'
_chemical_formula_weight         313.42
_chemical_name_systematic        'Beta Estradiol Acetontrile 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   difmap
_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                   6.98287(7)
_cell_length_b                   13.56289(14)
_cell_length_c                   18.1895(2)
_cell_measurement_reflns_used    18254
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      73.5390
_cell_measurement_theta_min      4.0170
_cell_volume                     1722.69(3)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(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    -49.00 -10.00   1.00    1.00    --  -42.62 -77.00  30.00   39
  2  \w    -55.00 -11.00   1.00    1.00    --  -42.62 -77.00 -60.00   44
  3  \w    -67.00 -15.00   1.00    1.00    --  -42.62 -57.00 -30.00   52
  4  \w    -84.00 -10.00   1.00    1.00    --  -42.62 -77.00 120.00   74
  5  \w      2.00  54.00   1.00    1.00    --   42.62 -99.00 120.00   52
  6  \w     33.00 119.00   1.00    1.15    --  106.36-125.00 120.00   86
  7  \w     34.00 118.00   1.00    1.15    --  106.36-125.00 -30.00   84
  8  \w     31.00 138.00   1.00    1.15    --  106.36 -77.00 120.00  107
  9  \w     77.00 172.00   1.00    1.15    --  106.36  61.00   0.00   95
 10  \w    142.00 177.00   1.00    1.15    --  106.36  77.00 -60.00   35
 11  \w    139.00 165.00   1.00    1.15    --  106.36  77.00-120.00   26
 12  \w    126.00 178.00   1.00    1.15    --  106.36  41.00-161.75   52
 13  \w    125.00 166.00   1.00    1.15    --  106.36  77.00 -30.00   41
 14  \w     94.00 171.00   1.00    1.15    --  106.36 125.00  90.00   77
 15  \w    112.00 176.00   1.00    1.15    --  106.36  77.00 150.00   64
 16  \w     77.00 105.00   1.00    1.15    --  106.36  61.00 120.00   28
 17  \w     77.00 103.00   1.00    1.15    --  106.36  61.00 150.00   26
 18  \w     74.00 100.00   1.00    1.15    --  106.36  77.00  90.00   26
 19  \w     74.00 100.00   1.00    1.15    --  106.36  77.00  60.00   26
 20  \w     74.00 173.00   1.00    1.15    --  106.36  77.00  30.00   99
 21  \w     78.00 159.00   1.00    1.15    --  106.36  61.00 -60.00   81
 22  \w     81.00 116.00   1.00    1.15    --  106.36  45.00-150.00   35
 23  \w     81.00 107.00   1.00    1.15    --  106.36  41.00-161.75   26
 24  \w     77.00 103.00   1.00    1.15    --  106.36  61.00-150.00   26
 25  \w     77.00 104.00   1.00    1.15    --  106.36  61.00-120.00   27
 26  \w     77.00 155.00   1.00    1.15    --  106.36  61.00 -90.00   78
 27  \w     78.00 103.00   1.00    1.15    --  106.36  61.00 -30.00   25
 28  \w     75.00 101.00   1.00    1.15    --  106.36  71.00   1.00   26
 29  \w     74.00 110.00   1.00    1.15    --  106.36  77.00 -30.00   36
 30  \w     77.00 103.00   1.00    1.15    --  106.36  61.00  30.00   26
 31  \w     77.00 103.00   1.00    1.15    --  106.36  61.00  60.00   26
 32  \w     77.00 156.00   1.00    1.15    --  106.36  61.00  90.00   79
 33  \w     74.00 110.00   1.00    1.15    --  106.36  77.00 150.00   36
 34  \w     74.00 118.00   1.00    1.15    --  106.36  77.00 120.00   44
 35  \w     74.00 100.00   1.00    1.15    --  106.36  77.00 -60.00   26
 36  \w     74.00 100.00   1.00    1.15    --  106.36  77.00 -90.00   26
 37  \w     74.00 132.00   1.00    1.15    --  106.36  77.00-120.00   58
 38  \w     74.00 100.00   1.00    1.15    --  106.36  77.00-150.00   26
 39  \w     28.00  86.00   1.00    1.15    --  106.36 -94.00  30.00   58
 40  \w    -65.00  28.00   1.00    1.00    --  -42.62  57.00-120.00   93
 41  \w    -92.00  -4.00   1.00    1.00    --  -42.62 125.00 -60.00   88
 42  \w   -116.00 -30.00   1.00    1.00    --  -42.62 -38.00-120.00   86
 43  \w   -109.00 -68.00   1.00    1.00    --  -42.62 -57.00 -30.00   41
 44  \w   -114.00 -10.00   1.00    1.00    --  -42.62 -77.00-150.00  104
 45  \w   -119.00 -88.00   1.00    1.00    --  -42.62 -77.00 120.00   31
;
_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      -0.0176894000
_diffrn_orient_matrix_UB_12      -0.1062467000
_diffrn_orient_matrix_UB_13      0.0292177000
_diffrn_orient_matrix_UB_21      -0.1459886000
_diffrn_orient_matrix_UB_22      -0.0237295000
_diffrn_orient_matrix_UB_23      -0.0609924000
_diffrn_orient_matrix_UB_31      0.1642633000
_diffrn_orient_matrix_UB_32      -0.0324626000
_diffrn_orient_matrix_UB_33      -0.0510594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25514
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.696
_diffrn_reflns_theta_min         4.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38218
_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    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Anhydrous Beta Estradiol Disolved in Dry Acetontirile'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0690P)^2^+0.1360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3344
_reflns_number_total             3456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01874j2.cif
_cod_data_source_block           xsrt0722
_cod_depositor_comments
'Adding full bibliography for 7231965--7231969.cif.'
_cod_database_code               7231968
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C20H27NO2
_chemical_oxdiff_usercomment     'Acetonitrile solvate'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
;
_shelx_res_checksum              60485
_olex2_date_sample_data_collection 2017-02-20
_olex2_exptl_crystal_mounting_method 'Nylon Loop'
_olex2_submission_original_sample_id 'Beta Estradiol Acetonitrile Solvate'
_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 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.496