A Chemoenzymatic Strategy for the Synthesis of Steroid Drugs Enabled by P450 Monooxygenase-Mediated Steroidal Core Modification
Peng, Yaqin; Gao, Chenghua; Zhang, Zili; Wu, Shijie; Zhao, Jing; Li, Aitao; ACS Catalysis  (2022) 2907–2914; doi:10.1021/acscatal.1c05776

data_4519327
_publ_section_title
;
 A Chemoenzymatic Strategy for the Synthesis of Steroid Drugs Enabled by
 P450 Monooxygenase-Mediated Steroidal Core Modification
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2907
_journal_page_last               2914
_journal_paper_doi               10.1021/acscatal.1c05776
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 O3'
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.35
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9764(5)
_cell_length_b                   10.4533(6)
_cell_length_c                   16.0723(10)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.74
_cell_measurement_theta_min      2.75
_cell_volume                     1508.11(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.999
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17168
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.735
_diffrn_reflns_theta_max         66.735
_diffrn_reflns_theta_min         5.047
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       brick
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0470P)^2^+0.1445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2386
_reflns_number_total             2663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05776_si_005.cif
_cod_data_source_block           651
_cod_database_code               4519327
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              30772
_shelx_hkl_checksum              78960