#------------------------------------------------------------------------------
#$Date: 2022-03-03 22:18:41 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273237 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519327.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4519327
loop_
_publ_author_name
'Peng, Yaqin'
'Gao, Chenghua'
'Zhang, Zili'
'Wu, Shijie'
'Zhao, Jing'
'Li, Aitao'
_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       'φ and ω 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/[σ²(Fo²)+(0.0470P)²+0.1445P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.923
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6871(2) 1.0886(2) 0.85050(14) 0.0653(6) Uani 1 1 d . . . . .
O2 O 0.64934(18) 0.84574(13) 0.48813(11) 0.0405(4) Uani 1 1 d . . . . .
H2A H 0.697300 0.872132 0.446670 0.061 Uiso 1 1 calc R U . . .
O3 O 0.45775(19) 0.36155(15) 0.46338(12) 0.0479(5) Uani 1 1 d . . . . .
C1 C 0.6885(3) 0.95630(19) 0.64508(16) 0.0360(5) Uani 1 1 d . . . . .
H1A H 0.619927 0.951824 0.596936 0.043 Uiso 1 1 calc R U . . .
H1B H 0.769243 1.017274 0.631304 0.043 Uiso 1 1 calc R U . . .
C2 C 0.6040(3) 1.0037(2) 0.72152(16) 0.0388(6) Uani 1 1 d . . . . .
H2B H 0.566308 1.091161 0.710916 0.047 Uiso 1 1 calc R U . . .
H2C H 0.517140 0.947372 0.731630 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7009(2) 1.0049(2) 0.79696(16) 0.0418(6) Uani 1 1 d . . . . .
C4 C 0.8070(2) 0.9014(2) 0.80398(16) 0.0400(6) Uani 1 1 d . . . . .
H4A H 0.864332 0.894198 0.853450 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8278(2) 0.8141(2) 0.74263(15) 0.0325(5) Uani 1 1 d . . . . .
C6 C 0.9314(2) 0.7036(2) 0.75519(16) 0.0365(5) Uani 1 1 d . . . . .
H6A H 0.958189 0.695702 0.814718 0.044 Uiso 1 1 calc R U . . .
H6B H 1.023894 0.716401 0.722694 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8511(2) 0.58363(19) 0.72589(15) 0.0328(5) Uani 1 1 d . . . . .
H7A H 0.757857 0.572610 0.757988 0.039 Uiso 1 1 calc R U . . .
H7B H 0.914858 0.507887 0.735898 0.039 Uiso 1 1 calc R U . . .
C8 C 0.8150(2) 0.59339(18) 0.63365(14) 0.0260(4) Uani 1 1 d . . . . .
H8A H 0.907768 0.575203 0.601325 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7561(2) 0.72533(18) 0.60762(14) 0.0256(5) Uani 1 1 d . . . . .
C10 C 0.7546(2) 0.82484(18) 0.66139(14) 0.0287(5) Uani 1 1 d . . . . .
C11 C 0.7112(2) 0.72754(17) 0.51590(14) 0.0281(5) Uani 1 1 d . . . . .
H11A H 0.804182 0.713259 0.482926 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6019(2) 0.62045(18) 0.49148(14) 0.0288(5) Uani 1 1 d . . . . .
H12A H 0.504674 0.635182 0.518974 0.035 Uiso 1 1 calc R U . . .
H12B H 0.585768 0.621813 0.430545 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6629(2) 0.49071(18) 0.51723(14) 0.0278(5) Uani 1 1 d . . . . .
C14 C 0.6977(2) 0.49433(18) 0.60986(13) 0.0254(4) Uani 1 1 d . . . . .
H14A H 0.603535 0.522176 0.637793 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7195(2) 0.35322(19) 0.63406(16) 0.0342(5) Uani 1 1 d . . . . .
H15A H 0.706181 0.340169 0.694616 0.041 Uiso 1 1 calc R U . . .
H15B H 0.819040 0.321692 0.617307 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5946(3) 0.2875(2) 0.58385(17) 0.0415(6) Uani 1 1 d . . . . .
H16A H 0.629478 0.204440 0.561554 0.050 Uiso 1 1 calc R U . . .
H16B H 0.506437 0.272167 0.619486 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5561(2) 0.37812(18) 0.51351(16) 0.0339(5) Uani 1 1 d . . . . .
C18 C 0.7975(2) 0.4497(2) 0.46345(16) 0.0386(5) Uani 1 1 d . . . . .
H18A H 0.871765 0.518411 0.462956 0.058 Uiso 1 1 calc R U . . .
H18B H 0.841904 0.372015 0.486840 0.058 Uiso 1 1 calc R U . . .
H18C H 0.764021 0.432779 0.406463 0.058 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2A 109.5 . . ?
C10 C1 C2 110.39(19) . . ?
C10 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
C10 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 111.53(19) . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2C 109.3 . . ?
C1 C2 H2C 109.3 . . ?
H2B C2 H2C 108.0 . . ?
O1 C3 C4 122.8(2) . . ?
O1 C3 C2 121.0(2) . . ?
C4 C3 C2 116.1(2) . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 H4A 118.7 . . ?
C3 C4 H4A 118.7 . . ?
C4 C5 C10 122.3(2) . . ?
C4 C5 C6 120.4(2) . . ?
C10 C5 C6 117.24(19) . . ?
C5 C6 C7 107.47(16) . . ?
C5 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 C8 110.33(18) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C14 110.24(17) . . ?
C7 C8 C9 113.53(17) . . ?
C14 C8 C9 107.71(15) . . ?
C7 C8 H8A 108.4 . . ?
C14 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C10 C9 C11 127.01(18) . . ?
C10 C9 C8 121.36(19) . . ?
C11 C9 C8 111.54(17) . . ?
C9 C10 C5 120.38(18) . . ?
C9 C10 C1 126.1(2) . . ?
C5 C10 C1 113.46(18) . . ?
O2 C11 C9 114.69(17) . . ?
O2 C11 C12 107.58(16) . . ?
C9 C11 C12 113.78(16) . . ?
O2 C11 H11A 106.8 . . ?
C9 C11 H11A 106.8 . . ?
C12 C11 H11A 106.8 . . ?
C13 C12 C11 110.46(16) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C17 C13 C12 116.94(16) . . ?
C17 C13 C14 100.79(17) . . ?
C12 C13 C14 108.55(17) . . ?
C17 C13 C18 104.86(16) . . ?
C12 C13 C18 112.12(18) . . ?
C14 C13 C18 113.18(17) . . ?
C13 C14 C8 113.80(17) . . ?
C13 C14 C15 104.45(17) . . ?
C8 C14 C15 119.99(17) . . ?
C13 C14 H14A 105.9 . . ?
C8 C14 H14A 105.9 . . ?
C15 C14 H14A 105.9 . . ?
C14 C15 C16 101.68(17) . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15B 111.4 . . ?
C16 C15 H15B 111.4 . . ?
H15A C15 H15B 109.3 . . ?
C17 C16 C15 106.12(17) . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
O3 C17 C16 125.10(19) . . ?
O3 C17 C13 126.8(2) . . ?
C16 C17 C13 108.12(18) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.233(3) . ?
O2 C11 1.426(2) . ?
O2 H2A 0.8400 . ?
O3 C17 1.208(3) . ?
C1 C10 1.520(3) . ?
C1 C2 1.527(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.492(4) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C4 1.446(3) . ?
C4 C5 1.356(3) . ?
C4 H4A 0.9500 . ?
C5 C10 1.466(3) . ?
C5 C6 1.496(3) . ?
C6 C7 1.521(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.525(3) . ?
C8 C9 1.535(3) . ?
C8 H8A 1.0000 . ?
C9 C10 1.352(3) . ?
C9 C11 1.529(3) . ?
C11 C12 1.540(3) . ?
C11 H11A 1.0000 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.519(3) . ?
C13 C14 1.522(3) . ?
C13 C18 1.546(3) . ?
C14 C15 1.538(3) . ?
C14 H14A 1.0000 . ?
C15 C16 1.542(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.515(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A O1 0.84 1.91 2.742(3) 173.2 2_674 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 56.0(2) . . . . ?
C1 C2 C3 O1 144.9(2) . . . . ?
C1 C2 C3 C4 -36.8(3) . . . . ?
O1 C3 C4 C5 -175.9(2) . . . . ?
C2 C3 C4 C5 5.7(3) . . . . ?
C3 C4 C5 C10 5.9(3) . . . . ?
C3 C4 C5 C6 -175.8(2) . . . . ?
C4 C5 C6 C7 133.1(2) . . . . ?
C10 C5 C6 C7 -48.5(3) . . . . ?
C5 C6 C7 C8 62.0(2) . . . . ?
C6 C7 C8 C14 -163.60(16) . . . . ?
C6 C7 C8 C9 -42.7(2) . . . . ?
C7 C8 C9 C10 7.1(3) . . . . ?
C14 C8 C9 C10 129.46(19) . . . . ?
C7 C8 C9 C11 -175.99(16) . . . . ?
C14 C8 C9 C11 -53.6(2) . . . . ?
C11 C9 C10 C5 -168.09(18) . . . . ?
C8 C9 C10 C5 8.3(3) . . . . ?
C11 C9 C10 C1 8.7(3) . . . . ?
C8 C9 C10 C1 -174.95(17) . . . . ?
C4 C5 C10 C9 -167.9(2) . . . . ?
C6 C5 C10 C9 13.7(3) . . . . ?
C4 C5 C10 C1 14.9(3) . . . . ?
C6 C5 C10 C1 -163.41(18) . . . . ?
C2 C1 C10 C9 138.1(2) . . . . ?
C2 C1 C10 C5 -45.0(2) . . . . ?
C10 C9 C11 O2 -5.9(3) . . . . ?
C8 C9 C11 O2 177.42(15) . . . . ?
C10 C9 C11 C12 -130.3(2) . . . . ?
C8 C9 C11 C12 53.0(2) . . . . ?
O2 C11 C12 C13 178.49(17) . . . . ?
C9 C11 C12 C13 -53.3(2) . . . . ?
C11 C12 C13 C17 168.08(19) . . . . ?
C11 C12 C13 C14 55.0(2) . . . . ?
C11 C12 C13 C18 -70.8(2) . . . . ?
C17 C13 C14 C8 175.34(15) . . . . ?
C12 C13 C14 C8 -61.3(2) . . . . ?
C18 C13 C14 C8 63.9(2) . . . . ?
C17 C13 C14 C15 42.66(19) . . . . ?
C12 C13 C14 C15 166.06(16) . . . . ?
C18 C13 C14 C15 -68.8(2) . . . . ?
C7 C8 C14 C13 -175.77(15) . . . . ?
C9 C8 C14 C13 59.9(2) . . . . ?
C7 C8 C14 C15 -51.1(2) . . . . ?
C9 C8 C14 C15 -175.42(19) . . . . ?
C13 C14 C15 C16 -40.4(2) . . . . ?
C8 C14 C15 C16 -169.42(19) . . . . ?
C14 C15 C16 C17 21.8(2) . . . . ?
C15 C16 C17 O3 -176.3(2) . . . . ?
C15 C16 C17 C13 4.2(2) . . . . ?
C12 C13 C17 O3 34.5(3) . . . . ?
C14 C13 C17 O3 151.9(2) . . . . ?
C18 C13 C17 O3 -90.4(3) . . . . ?
C12 C13 C17 C16 -146.0(2) . . . . ?
C14 C13 C17 C16 -28.6(2) . . . . ?
C18 C13 C17 C16 89.1(2) . . . . ?
