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#$Date: 2023-07-11 10:11:29 +0300 (Tue, 11 Jul 2023) $
#$Revision: 285140 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107457.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_8107457
loop_
_publ_author_name
'Chen, Ren-Song'
'Zhang, Jing-Jie'
'Zhang, Yi'
'Xu, Chuan-Yan'
'Ye, Jiang-Hai'
_publ_section_title
;
 Synthesis and crystal structure of
 (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one,
 C20H32O3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              417
_journal_page_last               419
_journal_paper_doi               10.1515/ncrs-2022-0546
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H32 O3'
_chemical_formula_weight         320.45
_chemical_name_systematic
;
(4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro
-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one
;
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8981(17)
_cell_length_b                   10.302(2)
_cell_length_c                   11.028(3)
_cell_measurement_reflns_used    4825
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.999
_cell_measurement_theta_min      2.706
_cell_volume                     897.3(4)
_computing_cell_refinement       'SAINT (Brucker, 2012)[2]'
_computing_data_collection       'APEX2 (Brucker, 2012)[2]'
_computing_data_reduction        'SAINT (Brucker, 2012)[2]'
_computing_molecular_graphics    'Diamond 4.0[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5323
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.004
_diffrn_reflns_theta_min         2.706
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0603
_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)+(0.0449P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.708
_reflns_number_gt                2583
_reflns_number_total             4825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0546_suppl.cif
_cod_data_source_block           A_a
_cod_original_cell_volume        897.3(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8107457
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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 0.6734(3) 0.2919(2) 0.3986(2) 0.0530(7) Uani 1 1 d . . . . .
C1 C 0.3929(4) 0.4837(3) 0.4476(3) 0.0411(9) Uani 1 1 d . . . . .
H1A H 0.380995 0.412992 0.504986 0.049 Uiso 1 1 calc R U . . .
H1AB H 0.333720 0.558234 0.480651 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3081(5) 0.4447(4) 0.3289(3) 0.0510(9) Uani 1 1 d . . . . .
H2A H 0.356020 0.363558 0.300538 0.061 Uiso 1 1 calc R U . . .
H2AB H 0.188054 0.431422 0.342639 0.061 Uiso 1 1 calc R U . . .
O2 O 0.8512(3) 0.4320(2) 0.4890(2) 0.0384(6) Uani 1 1 d . . . . .
O3 O 0.9047(4) 0.3847(2) 0.7534(2) 0.0559(7) Uani 1 1 d . . . . .
H3 H 0.882811 0.361071 0.684114 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3325(5) 0.5482(4) 0.2333(4) 0.0515(10) Uani 1 1 d . . . . .
H3A H 0.280874 0.628338 0.261039 0.062 Uiso 1 1 calc R U . . .
H3AB H 0.274820 0.521785 0.159642 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5202(5) 0.5734(4) 0.2045(3) 0.0441(9) Uani 1 1 d . . . . .
C6 C 0.8089(4) 0.6237(4) 0.3073(3) 0.0449(9) Uani 1 1 d . . . . .
H6A H 0.855041 0.544152 0.273758 0.054 Uiso 1 1 calc R U . . .
H6AB H 0.829594 0.692786 0.249438 0.054 Uiso 1 1 calc R U . . .
C5 C 0.6175(4) 0.6076(3) 0.3242(3) 0.0355(8) Uani 1 1 d . . . . .
H5 H 0.576065 0.693593 0.347961 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8441(4) 0.5697(3) 0.5310(3) 0.0351(8) Uani 1 1 d . . . . .
C7 C 0.9012(4) 0.6552(4) 0.4258(3) 0.0417(9) Uani 1 1 d . . . . .
H7A H 1.021935 0.643993 0.413791 0.050 Uiso 1 1 calc R U . . .
H7AB H 0.881165 0.745389 0.446456 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6529(4) 0.5857(3) 0.5513(3) 0.0338(7) Uani 1 1 d . . . . .
H9 H 0.622414 0.677940 0.551002 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5819(4) 0.5177(3) 0.4360(3) 0.0336(7) Uani 1 1 d . . . . .
C11 C 0.5965(4) 0.5222(4) 0.6700(3) 0.0420(9) Uani 1 1 d . . . . .
H11A H 0.480102 0.546565 0.686523 0.050 Uiso 1 1 calc R U . . .
H11B H 0.600275 0.428615 0.660794 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7069(4) 0.5615(4) 0.7772(3) 0.0440(9) Uani 1 1 d . . . . .
H12A H 0.664368 0.519595 0.849889 0.053 Uiso 1 1 calc R U . . .
H12B H 0.698090 0.654564 0.788960 0.053 Uiso 1 1 calc R U . . .
C13 C 0.8931(4) 0.5255(3) 0.7605(3) 0.0412(8) Uani 1 1 d . . . . .
C14 C 0.9573(4) 0.5852(3) 0.6417(3) 0.0416(8) Uani 1 1 d . . . . .
H14A H 0.975277 0.677280 0.655101 0.050 Uiso 1 1 calc R U . . .
H14B H 1.066516 0.547096 0.623234 0.050 Uiso 1 1 calc R U . . .
C15 C 1.0019(5) 0.5633(4) 0.8717(3) 0.0563(10) Uani 1 1 d . . . . .
H15 H 0.958460 0.513253 0.940575 0.068 Uiso 1 1 calc R U . . .
C16 C 1.1877(5) 0.5248(6) 0.8562(5) 0.0846(17) Uani 1 1 d . . . . .
H16A H 1.194572 0.435086 0.833299 0.127 Uiso 1 1 calc R U . . .
H16B H 1.246856 0.537841 0.931250 0.127 Uiso 1 1 calc R U . . .
H16C H 1.238324 0.577467 0.794132 0.127 Uiso 1 1 calc R U . . .
C17 C 0.9914(6) 0.7060(5) 0.9077(5) 0.0847(16) Uani 1 1 d . . . . .
H17A H 1.033624 0.758815 0.842748 0.127 Uiso 1 1 calc R U . . .
H17B H 1.058302 0.720423 0.979171 0.127 Uiso 1 1 calc R U . . .
H17C H 0.875658 0.728469 0.923976 0.127 Uiso 1 1 calc R U . . .
C18 C 0.5942(5) 0.4546(4) 0.1382(4) 0.0594(11) Uani 1 1 d . . . . .
H18A H 0.527554 0.436426 0.067410 0.089 Uiso 1 1 calc R U . . .
H18B H 0.592320 0.380856 0.191370 0.089 Uiso 1 1 calc R U . . .
H18C H 0.708762 0.472645 0.114584 0.089 Uiso 1 1 calc R U . . .
C19 C 0.5287(5) 0.6915(4) 0.1180(4) 0.0611(12) Uani 1 1 d . . . . .
H19A H 0.644044 0.706320 0.094445 0.092 Uiso 1 1 calc R U . . .
H19B H 0.485736 0.766999 0.158745 0.092 Uiso 1 1 calc R U . . .
H19C H 0.461467 0.674460 0.047236 0.092 Uiso 1 1 calc R U . . .
C20 C 0.6995(4) 0.4006(3) 0.4358(3) 0.0361(8) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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
C2 C1 C10 114.5(3) . .
C2 C1 H1A 108.6 . .
C10 C1 H1A 108.6 . .
C2 C1 H1AB 108.6 . .
C10 C1 H1AB 108.6 . .
H1A C1 H1AB 107.6 . .
C3 C2 C1 110.9(3) . .
C3 C2 H2A 109.5 . .
C1 C2 H2A 109.5 . .
C3 C2 H2AB 109.5 . .
C1 C2 H2AB 109.5 . .
H2A C2 H2AB 108.0 . .
C20 O2 C8 108.9(2) . .
C13 O3 H3 109.5 . .
C2 C3 C4 112.7(3) . .
C2 C3 H3A 109.1 . .
C4 C3 H3A 109.1 . .
C2 C3 H3AB 109.1 . .
C4 C3 H3AB 109.1 . .
H3A C3 H3AB 107.8 . .
C3 C4 C18 109.3(3) . .
C3 C4 C19 107.6(3) . .
C18 C4 C19 108.4(3) . .
C3 C4 C5 109.7(3) . .
C18 C4 C5 113.1(3) . .
C19 C4 C5 108.7(3) . .
C7 C6 C5 112.8(3) . .
C7 C6 H6A 109.0 . .
C5 C6 H6A 109.0 . .
C7 C6 H6AB 109.0 . .
C5 C6 H6AB 109.0 . .
H6A C6 H6AB 107.8 . .
C6 C5 C4 113.9(3) . .
C6 C5 C10 109.7(3) . .
C4 C5 C10 116.2(3) . .
C6 C5 H5 105.3 . .
C4 C5 H5 105.3 . .
C10 C5 H5 105.3 . .
O2 C8 C14 109.1(3) . .
O2 C8 C7 107.5(2) . .
C14 C8 C7 112.1(3) . .
O2 C8 C9 100.6(2) . .
C14 C8 C9 116.7(2) . .
C7 C8 C9 109.9(3) . .
C8 C7 C6 112.7(3) . .
C8 C7 H7A 109.0 . .
C6 C7 H7A 109.0 . .
C8 C7 H7AB 109.0 . .
C6 C7 H7AB 109.0 . .
H7A C7 H7AB 107.8 . .
C11 C9 C8 111.4(3) . .
C11 C9 C10 113.6(3) . .
C8 C9 C10 100.8(2) . .
C11 C9 H9 110.2 . .
C8 C9 H9 110.2 . .
C10 C9 H9 110.2 . .
C20 C10 C1 114.3(3) . .
C20 C10 C9 98.0(3) . .
C1 C10 C9 112.6(3) . .
C20 C10 C5 110.9(2) . .
C1 C10 C5 112.0(3) . .
C9 C10 C5 108.1(2) . .
C12 C11 C9 112.6(3) . .
C12 C11 H11A 109.1 . .
C9 C11 H11A 109.1 . .
C12 C11 H11B 109.1 . .
C9 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
C11 C12 C13 113.1(3) . .
C11 C12 H12A 109.0 . .
C13 C12 H12A 109.0 . .
C11 C12 H12B 109.0 . .
C13 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
O3 C13 C12 108.0(3) . .
O3 C13 C14 109.4(3) . .
C12 C13 C14 108.9(3) . .
O3 C13 C15 105.0(3) . .
C12 C13 C15 112.2(3) . .
C14 C13 C15 113.1(3) . .
C8 C14 C13 116.7(3) . .
C8 C14 H14A 108.1 . .
C13 C14 H14A 108.1 . .
C8 C14 H14B 108.1 . .
C13 C14 H14B 108.1 . .
H14A C14 H14B 107.3 . .
C17 C15 C16 109.4(4) . .
C17 C15 C13 114.8(4) . .
C16 C15 C13 112.2(3) . .
C17 C15 H15 106.7 . .
C16 C15 H15 106.7 . .
C13 C15 H15 106.7 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C4 C18 H18A 109.5 . .
C4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 C19 H19A 109.5 . .
C4 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C4 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O1 C20 O2 120.8(3) . .
O1 C20 C10 129.0(3) . .
O2 C20 C10 110.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C20 1.210(4) .
C1 C2 1.524(5) .
C1 C10 1.538(4) .
C1 H1A 0.9700 .
C1 H1AB 0.9700 .
C2 C3 1.512(5) .
C2 H2A 0.9700 .
C2 H2AB 0.9700 .
O2 C20 1.372(4) .
O2 C8 1.494(4) .
O3 C13 1.455(4) .
O3 H3 0.8200 .
C3 C4 1.538(5) .
C3 H3A 0.9700 .
C3 H3AB 0.9700 .
C4 C18 1.540(5) .
C4 C19 1.547(5) .
C4 C5 1.568(5) .
C6 C7 1.530(5) .
C6 C5 1.532(4) .
C6 H6A 0.9700 .
C6 H6AB 0.9700 .
C5 C10 1.568(4) .
C5 H5 0.9800 .
C8 C14 1.521(5) .
C8 C7 1.525(4) .
C8 C9 1.535(4) .
C7 H7A 0.9700 .
C7 H7AB 0.9700 .
C9 C11 1.530(4) .
C9 C10 1.556(4) .
C9 H9 0.9800 .
C10 C20 1.523(4) .
C11 C12 1.524(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.528(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.534(5) .
C13 C15 1.547(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C17 1.524(6) .
C15 C16 1.530(5) .
C15 H15 0.9800 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
