Synthesis and structural elucidation of a dehydrochloromethyltestosterone metabolite.
Kratena, Nicolas; Pilz, Sarah M.; Weil, Matthias; Gmeiner, Günter; Enev, Valentin S.; Gärtner, Peter; Organic & biomolecular chemistry 16 (2018) 2508–2521; doi:10.1039/C8OB00122G

data_7156144
_publ_section_title
;
 Synthesis and structural elucidation of a dehydrochloromethyltestosterone
 metabolite.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2508
_journal_page_last               2521
_journal_paper_doi               10.1039/C8OB00122G
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H27 Cl O2'
_chemical_formula_sum            'C19 H27 Cl O2'
_chemical_formula_weight         322.85
_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   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-11-20 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4333(17)
_cell_length_b                   13.538(3)
_cell_length_c                   16.411(4)
_cell_measurement_reflns_used    8379
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.957
_cell_measurement_theta_min      2.982
_cell_volume                     1651.5(7)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w- and \f-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33711
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.993
_diffrn_reflns_theta_min         2.482
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       fragment
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.038(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         7201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.1722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                6793
_reflns_number_total             7201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00122g2.cif
_cod_data_source_block           23
_cod_depositor_comments
'Adding full bibliography for 7156140--7156144.cif.'
_cod_original_cell_volume        1651.4(7)
_cod_database_code               7156144
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              35466