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_7231965
_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 ad
_chemical_formula_moiety         '2(C18 H24 O2), C H4 O'
_chemical_formula_sum            'C37 H52 O5'
_chemical_formula_weight         576.78
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-06
_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                89.7413(17)
_cell_angle_beta                 88.0129(17)
_cell_angle_gamma                70.786(2)
_cell_formula_units_Z            1
_cell_length_a                   7.31144(16)
_cell_length_b                   9.2985(2)
_cell_length_c                   12.3778(2)
_cell_measurement_reflns_used    11196
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      73.4360
_cell_measurement_theta_min      5.0020
_cell_volume                     794.14(3)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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      150(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -39.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000    0.0000 25

  2 omega  -75.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000    0.0000 31

  3 omega -116.00  -78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000    0.0000 38

  4 omega  -44.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  -30.0000 72

  5 omega    3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   87.0000    1.5008 25

  6 omega  -54.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000  150.0000 36

  7 omega  -49.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  150.0000 81

  8 omega   18.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000   93.4037 28

  9 omega   30.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000   50.3206 27

 10 omega   37.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   87.8740 40

 11 omega   55.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   70.0000   55.8068 31

 12 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 100

 13 omega  139.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   60.0000 27

 14 omega  147.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 31

 15 omega  127.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 44

 16 omega  116.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 26

 17 omega  100.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  153.7628 26

 18 omega   74.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 95

 19 omega  102.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000    8.1678 31

 20 omega  110.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   75.0000  -52.7558 54

 21 omega  129.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 47

 22 omega  122.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 55

 23 omega   97.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   73.0000 -157.3639 53

 24 omega   78.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 92

 25 omega   79.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -120.0000 32

 26 omega   79.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 30

 27 omega   74.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 49

 28 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 26

 29 omega   74.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -90.0000 74

 30 omega   74.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   60.0000 57

 31 omega   78.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 33

 32 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 27

 33 omega   75.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 96

 34 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 26

 35 omega   74.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 83

 36 omega   59.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   75.0000  -52.7558 28

 37 omega   44.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -36.3378 41

 38 omega   39.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   74.0000  -48.7086 27

 39 omega   35.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  -87.9210 29

 40 omega   31.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000 -148.5435 28

 41 omega   54.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   73.0000 -157.3639 29

 42 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -112.8352 25

 43 omega   15.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216   57.0000 -150.0000 25

 44 omega    3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   84.0000 -110.6055 25

 45 omega   16.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  -28.7088 25

 46 omega   26.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000    8.1678 44

 47 omega   31.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  153.7628 26

 48 omega   37.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  160.4528 28

 49 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  178.4157 25

 50 omega   49.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000  -60.0000 88

 51 omega   93.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000   60.0000 26

 52 omega   39.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -124.0000  -26.0000 59

 53 omega   36.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000 -180.0000 83

 54 omega   30.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000 -180.0000 92

 55 omega -108.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000  150.0000 49
;
_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      0.0142673000
_diffrn_orient_matrix_UB_12      -0.0434699000
_diffrn_orient_matrix_UB_13      -0.1207034000
_diffrn_orient_matrix_UB_21      0.0567311000
_diffrn_orient_matrix_UB_22      0.1414884000
_diffrn_orient_matrix_UB_23      -0.0286337000
_diffrn_orient_matrix_UB_31      0.2154742000
_diffrn_orient_matrix_UB_32      -0.0942154000
_diffrn_orient_matrix_UB_33      0.0109955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11899
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.595
_diffrn_reflns_theta_min         5.037
_diffrn_source                   microscource
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) 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    1.206
_exptl_crystal_F_000             314
_exptl_crystal_recrystallization_method 'Crystalised from methanol'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 2620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         5763
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0610P)^2^+0.0240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                5747
_reflns_number_total             5763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01874j2.cif
_cod_data_source_block           xstr0662
_cod_depositor_comments
'Adding full bibliography for 7231965--7231969.cif.'
_cod_database_code               7231965
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H24 O2'
_chemical_oxdiff_usercomment     'Estradiol methanol solvate'
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
;
_shelx_res_checksum              11711
_olex2_date_sample_data_collection 2016-10-25
_olex2_submission_original_sample_id XSTR0662
_olex2_submission_special_instructions 'No special instructions were received'