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_7156142
_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         'C26 H45 Cl O2 Si'
_chemical_formula_sum            'C26 H45 Cl O2 Si'
_chemical_formula_weight         453.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-02-26 deposited with the CCDC.
2018-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.170(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2696(16)
_cell_length_b                   7.0208(8)
_cell_length_c                   28.171(3)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.106
_cell_measurement_theta_min      3.095
_cell_volume                     2604.0(5)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX-3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            24646
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         3.089
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  .5500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         6247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.275
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0392P)^2^+6.2520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                6013
_reflns_number_total             6247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00122g2.cif
_cod_data_source_block           sad_a
_cod_depositor_comments
'Adding full bibliography for 7156140--7156144.cif.'
_cod_database_code               7156142
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              65996