Structure-activity studies of non-steroid analogues structurally-related to neuroprotective estrogens.
Qian, Mingxing; Engler-Chiurazzi, Elizabeth B; Lewis, Sara E.; Rath, Nigam P.; Simpkins, James W.; Covey, Douglas F.; Organic & biomolecular chemistry 14 (2016) 9790–9805; doi:10.1039/c6ob01726f

data_1544171
_publ_section_title
;
 Structure-activity studies of non-steroid analogues structurally-related
 to neuroprotective estrogens.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9790
_journal_page_last               9805
_journal_paper_doi               10.1039/c6ob01726f
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H24 O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C18.5 H25 Cl O2'
_chemical_formula_weight         314.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-01 deposited with the CCDC.
2016-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.162(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6590(4)
_cell_length_b                   20.7140(10)
_cell_length_c                   10.7415(6)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.63
_cell_measurement_theta_min      2.66
_cell_volume                     1702.91(15)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            38876
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.449
_diffrn_reflns_theta_min         1.897
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1913 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.9(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6242
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.2383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4814
_reflns_number_total             6242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01726f3.cif
_cod_data_source_block           d27909_sq
_cod_depositor_comments
;
Adding full bibliography for 1544171--1544174.cif.

2019-02-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C37 H50 Cl2 O4'
_cod_original_formula_weight         629.67
_cod_original_formula_moiety         '2(C18 H24 O2), C H2 Cl2'
_cod_original_formula_units_Z            2
_cod_database_code               1544171
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              26873
_shelx_fab_checksum              11843