#------------------------------------------------------------------------------
#$Date: 2023-05-11 10:20:30 +0300 (Thu, 11 May 2023) $
#$Revision: 283682 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107179.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_8107179
loop_
_publ_author_name
'Ji, Xiao-Liang'
'Xie, Feng'
'Li, Yi-Biao'
_publ_section_title
;
 The crystal structure of 17-(bromoethynyl)-17-hydroxy-10, 13-dimethyl-
 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one,
 C21H27BrO2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              655
_journal_page_last               657
_journal_paper_doi               10.1515/ncrs-2022-0165
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H27 Br O2'
_chemical_formula_sum            'C21 H27 Br O2'
_chemical_formula_weight         391.33
_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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 95.0757(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.62197(14)
_cell_length_b                   11.7640(2)
_cell_length_c                   11.8485(2)
_cell_measurement_reflns_used    4521
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6270
_cell_measurement_theta_min      3.7530
_cell_volume                     919.39(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -65.00  17.00   1.00    1.00    --  -40.73  57.00  30.00   82
  2  ω    -30.00  -3.00   1.00    1.00    --  -40.73 125.00-150.00   27
  3  ω   -114.00 -22.00   1.00    1.00    --  -40.73 -38.00  30.00   92
  4  ω    148.00 175.00   1.00    1.00    --  107.58  30.00  30.00   27
  5  ω    109.00 173.00   1.00    1.00    --  107.58 125.00-120.00   64
  6  ω     97.00 172.00   1.00    1.00    --  107.58 125.00-150.00   75
  7  ω     97.00 174.00   1.00    1.00    --  107.58  45.00   0.00   77
  8  ω     40.00 129.00   1.00    1.00    --  107.58 -45.00-150.00   89
  9  ω     26.00  89.00   1.00    1.00    --  107.58 -95.00-180.00   63
 10  ω   -101.00 -23.00   1.00    1.00    --  -40.98 -57.00 120.00   78
 11  ω    -60.00 -27.00   1.00    1.00    --  -40.98 -57.00  30.00   33
 12  ω     63.00  93.00   1.00    1.00    --   40.98-125.00-150.00   30
 13  ω     23.00  77.00   1.00    1.00    --   40.98-125.00 -60.00   54
 14  ω     30.00  56.00   1.00    1.00    --   40.98-125.00-150.00   26
 15  ω    152.00 178.00   1.00    1.00    --  107.58  61.00 120.00   26
 16  ω     78.00 111.00   1.00    1.00    --  107.58  61.00 120.00   33
 17  ω     83.00 113.00   1.00    1.00    --  107.58  45.00  60.00   30
 18  ω     75.00 101.00   1.00    1.00    --  107.58  77.00  60.00   26
 19  ω     82.00  96.00   1.00    1.00    --  107.58  45.00  90.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1749550000
_diffrn_orient_matrix_UB_12      -0.0075453000
_diffrn_orient_matrix_UB_13      0.0944229000
_diffrn_orient_matrix_UB_21      -0.1434364000
_diffrn_orient_matrix_UB_22      -0.0566317000
_diffrn_orient_matrix_UB_23      0.0788035000
_diffrn_orient_matrix_UB_31      0.0576297000
_diffrn_orient_matrix_UB_32      -0.1178203000
_diffrn_orient_matrix_UB_33      -0.0439310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5032
_diffrn_reflns_point_group_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.787
_diffrn_reflns_theta_min         3.745
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0264
_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)+(0.0487P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                3117
_reflns_number_total             3136
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0165_suppl.cif
_cod_data_source_block           b5
_cod_database_code               8107179
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.456
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
Br1 Br 0.57735(4) 0.73015(4) 0.02963(2) 0.02312(11) Uani 1 1 d . . . . .
O1 O 0.8707(5) 0.4905(3) 0.8885(3) 0.0375(8) Uani 1 1 d . . . . .
O2 O 0.1317(4) 0.3783(2) 0.0460(2) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.080(10) 0.407(7) -0.013(6) 0.08(2) Uiso 1 1 d . . . . .
C1 C 0.4423(5) 0.4721(3) 0.6846(3) 0.0182(6) Uani 1 1 d . . . . .
C2 C 0.5656(6) 0.5079(3) 0.7731(3) 0.0239(7) Uani 1 1 d . . . . .
H2A H 0.527705 0.571802 0.812338 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7573(6) 0.4518(3) 0.8114(3) 0.0244(7) Uani 1 1 d . . . . .
C4 C 0.8025(5) 0.3438(3) 0.7510(3) 0.0205(6) Uani 1 1 d . . . . .
H4A H 0.737225 0.280412 0.785528 0.025 Uiso 1 1 calc R U . . .
H4B H 0.947568 0.330182 0.758283 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7265(5) 0.3516(3) 0.6258(3) 0.0186(6) Uani 1 1 d . . . . .
H5A H 0.754962 0.280463 0.589050 0.022 Uiso 1 1 calc R U . . .
H5B H 0.800738 0.411148 0.590759 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4980(5) 0.3767(3) 0.6057(3) 0.0155(6) Uani 1 1 d . . . . .
C7 C 0.4464(4) 0.4166(3) 0.4810(2) 0.0145(6) Uani 1 1 d . . . . .
H7 H 0.530774 0.483716 0.471017 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2240(4) 0.4567(3) 0.4577(2) 0.0147(6) Uani 1 1 d . . . . .
H8 H 0.133400 0.393500 0.472173 0.018 Uiso 1 1 calc R U . . .
C9 C 0.1848(5) 0.5550(3) 0.5373(3) 0.0190(6) Uani 1 1 d . . . . .
H9A H 0.266286 0.619795 0.518928 0.023 Uiso 1 1 calc R U . . .
H9B H 0.043319 0.577037 0.525444 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2346(5) 0.5238(3) 0.6614(3) 0.0220(7) Uani 1 1 d . . . . .
H10A H 0.226384 0.591657 0.707314 0.026 Uiso 1 1 calc R U . . .
H10B H 0.134116 0.470364 0.683863 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5056(5) 0.3284(3) 0.3925(3) 0.0173(6) Uani 1 1 d . . . . .
H11A H 0.650469 0.314959 0.403711 0.021 Uiso 1 1 calc R U . . .
H11B H 0.437713 0.257121 0.405577 0.021 Uiso 1 1 calc R U . . .
C12 C 0.4510(5) 0.3653(3) 0.2695(3) 0.0182(6) Uani 1 1 d . . . . .
H12A H 0.533830 0.429992 0.252332 0.022 Uiso 1 1 calc R U . . .
H12B H 0.480128 0.303731 0.219012 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2272(5) 0.3974(2) 0.2495(2) 0.0148(6) Uani 1 1 d . . . . .
C14 C 0.1858(4) 0.4924(3) 0.3343(2) 0.0151(6) Uani 1 1 d . . . . .
H14 H 0.281437 0.553885 0.322401 0.018 Uiso 1 1 calc R U . . .
C15 C -0.0264(5) 0.5366(3) 0.2923(3) 0.0204(6) Uani 1 1 d . . . . .
H15A H -0.040006 0.616465 0.310348 0.025 Uiso 1 1 calc R U . . .
H15B H -0.130904 0.494089 0.326430 0.025 Uiso 1 1 calc R U . . .
C16 C -0.0415(5) 0.5180(3) 0.1622(3) 0.0217(7) Uani 1 1 d . . . . .
H16A H -0.056540 0.590186 0.122805 0.026 Uiso 1 1 calc R U . . .
H16B H -0.157113 0.470440 0.138385 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1595(5) 0.4586(3) 0.1360(3) 0.0186(7) Uani 1 1 d . . . . .
C18 C 0.3076(5) 0.5458(3) 0.1060(3) 0.0198(6) Uani 1 1 d . . . . .
C19 C 0.4139(5) 0.6188(3) 0.0764(3) 0.0217(7) Uani 1 1 d . . . . .
C20 C 0.3767(5) 0.2695(3) 0.6323(3) 0.0198(6) Uani 1 1 d . . . . .
H20A H 0.405844 0.249520 0.710645 0.030 Uiso 1 1 calc R U . . .
H20B H 0.414356 0.207779 0.585503 0.030 Uiso 1 1 calc R U . . .
H20C H 0.234277 0.284421 0.617410 0.030 Uiso 1 1 calc R U . . .
C21 C 0.0920(5) 0.2920(3) 0.2597(3) 0.0226(7) Uani 1 1 d . . . . .
H21A H -0.047996 0.313918 0.248361 0.034 Uiso 1 1 calc R U . . .
H21B H 0.118667 0.259260 0.333754 0.034 Uiso 1 1 calc R U . . .
H21C H 0.121021 0.237146 0.203402 0.034 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'
Br Br -0.6763 1.2805 '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
C17 O2 H2 112(5) . .
C2 C1 C6 123.2(3) . .
C2 C1 C10 120.0(3) . .
C10 C1 C6 116.8(3) . .
C1 C2 H2A 118.2 . .
C1 C2 C3 123.5(3) . .
C3 C2 H2A 118.2 . .
O1 C3 C2 121.5(3) . .
O1 C3 C4 122.5(3) . .
C2 C3 C4 115.9(3) . .
C3 C4 H4A 109.6 . .
C3 C4 H4B 109.6 . .
C3 C4 C5 110.4(3) . .
H4A C4 H4B 108.1 . .
C5 C4 H4A 109.6 . .
C5 C4 H4B 109.6 . .
C4 C5 H5A 108.9 . .
C4 C5 H5B 108.9 . .
C4 C5 C6 113.4(3) . .
H5A C5 H5B 107.7 . .
C6 C5 H5A 108.9 . .
C6 C5 H5B 108.9 . .
C1 C6 C5 109.5(3) . .
C1 C6 C7 108.3(2) . .
C1 C6 C20 108.5(3) . .
C5 C6 C7 109.5(2) . .
C5 C6 C20 109.5(3) . .
C20 C6 C7 111.4(2) . .
C6 C7 H7 106.1 . .
C8 C7 C6 112.7(2) . .
C8 C7 H7 106.1 . .
C8 C7 C11 112.1(2) . .
C11 C7 C6 113.1(2) . .
C11 C7 H7 106.1 . .
C7 C8 H8 109.0 . .
C9 C8 C7 109.3(2) . .
C9 C8 H8 109.0 . .
C14 C8 C7 109.3(2) . .
C14 C8 H8 109.0 . .
C14 C8 C9 111.2(2) . .
C8 C9 H9A 109.1 . .
C8 C9 H9B 109.1 . .
H9A C9 H9B 107.9 . .
C10 C9 C8 112.3(3) . .
C10 C9 H9A 109.1 . .
C10 C9 H9B 109.1 . .
C1 C10 C9 113.0(3) . .
C1 C10 H10A 109.0 . .
C1 C10 H10B 109.0 . .
C9 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C7 C11 H11A 108.8 . .
C7 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C12 C11 C7 113.6(2) . .
C12 C11 H11A 108.8 . .
C12 C11 H11B 108.8 . .
C11 C12 H12A 109.4 . .
C11 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
C13 C12 C11 111.2(3) . .
C13 C12 H12A 109.4 . .
C13 C12 H12B 109.4 . .
C12 C13 C14 107.7(2) . .
C12 C13 C17 116.7(3) . .
C12 C13 C21 110.6(3) . .
C14 C13 C17 100.0(2) . .
C21 C13 C14 113.2(3) . .
C21 C13 C17 108.4(3) . .
C8 C14 C13 113.7(2) . .
C8 C14 H14 106.7 . .
C8 C14 C15 118.2(3) . .
C13 C14 H14 106.7 . .
C15 C14 C13 104.1(2) . .
C15 C14 H14 106.7 . .
C14 C15 H15A 110.9 . .
C14 C15 H15B 110.9 . .
C14 C15 C16 104.5(2) . .
H15A C15 H15B 108.9 . .
C16 C15 H15A 110.9 . .
C16 C15 H15B 110.9 . .
C15 C16 H16A 110.5 . .
C15 C16 H16B 110.5 . .
C15 C16 C17 106.3(2) . .
H16A C16 H16B 108.7 . .
C17 C16 H16A 110.5 . .
C17 C16 H16B 110.5 . .
O2 C17 C13 110.4(3) . .
O2 C17 C16 113.0(3) . .
O2 C17 C18 108.9(3) . .
C13 C17 C16 102.7(3) . .
C18 C17 C13 112.4(3) . .
C18 C17 C16 109.4(3) . .
C19 C18 C17 174.8(3) . .
C18 C19 Br1 179.4(3) . .
C6 C20 H20A 109.5 . .
C6 C20 H20B 109.5 . .
C6 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C13 C21 H21A 109.5 . .
C13 C21 H21B 109.5 . .
C13 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C19 1.817(3) .
O1 C3 1.218(4) .
O2 H2 0.82(7) .
O2 C17 1.424(4) .
C1 C2 1.338(5) .
C1 C6 1.526(4) .
C1 C10 1.506(4) .
C2 H2A 0.9300 .
C2 C3 1.467(5) .
C3 C4 1.502(5) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C4 C5 1.527(4) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C5 C6 1.539(4) .
C6 C7 1.560(4) .
C6 C20 1.544(4) .
C7 H7 0.9800 .
C7 C8 1.548(4) .
C7 C11 1.550(4) .
C8 H8 0.9800 .
C8 C9 1.529(4) .
C8 C14 1.521(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.523(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.533(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.528(4) .
C13 C14 1.542(4) .
C13 C17 1.557(4) .
C13 C21 1.541(4) .
C14 H14 0.9800 .
C14 C15 1.539(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.552(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C17 1.558(5) .
C17 C18 1.483(5) .
C18 C19 1.183(5) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
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
O1 C3 C4 C5 -145.0(4) . . . .
C1 C2 C3 O1 176.0(4) . . . .
C1 C2 C3 C4 -4.9(5) . . . .
C1 C6 C7 C8 -54.1(3) . . . .
C1 C6 C7 C11 177.5(2) . . . .
C2 C1 C6 C5 -13.7(4) . . . .
C2 C1 C6 C7 -133.1(3) . . . .
C2 C1 C6 C20 105.8(4) . . . .
C2 C1 C10 C9 133.7(3) . . . .
C2 C3 C4 C5 35.9(4) . . . .
C3 C4 C5 C6 -57.5(4) . . . .
C4 C5 C6 C1 45.5(4) . . . .
C4 C5 C6 C7 164.2(3) . . . .
C4 C5 C6 C20 -73.4(3) . . . .
C5 C6 C7 C8 -173.5(3) . . . .
C5 C6 C7 C11 58.0(3) . . . .
C6 C1 C2 C3 -6.9(5) . . . .
C6 C1 C10 C9 -48.3(4) . . . .
C6 C7 C8 C9 58.9(3) . . . .
C6 C7 C8 C14 -179.2(2) . . . .
C6 C7 C11 C12 178.6(3) . . . .
C7 C8 C9 C10 -55.6(3) . . . .
C7 C8 C14 C13 58.0(3) . . . .
C7 C8 C14 C15 -179.4(3) . . . .
C7 C11 C12 C13 -53.7(4) . . . .
C8 C7 C11 C12 49.9(4) . . . .
C8 C9 C10 C1 50.4(4) . . . .
C8 C14 C15 C16 -157.7(3) . . . .
C9 C8 C14 C13 178.8(2) . . . .
C9 C8 C14 C15 -58.6(3) . . . .
C10 C1 C2 C3 171.0(3) . . . .
C10 C1 C6 C5 168.3(3) . . . .
C10 C1 C6 C7 48.9(4) . . . .
C10 C1 C6 C20 -72.2(3) . . . .
C11 C7 C8 C9 -172.2(2) . . . .
C11 C7 C8 C14 -50.2(3) . . . .
C11 C12 C13 C14 57.1(3) . . . .
C11 C12 C13 C17 168.5(3) . . . .
C11 C12 C13 C21 -67.1(3) . . . .
C12 C13 C14 C8 -61.5(3) . . . .
C12 C13 C14 C15 168.4(2) . . . .
C12 C13 C17 O2 80.0(3) . . . .
C12 C13 C17 C16 -159.3(3) . . . .
C12 C13 C17 C18 -41.8(4) . . . .
C13 C14 C15 C16 -30.4(3) . . . .
C14 C8 C9 C10 -176.4(3) . . . .
C14 C13 C17 O2 -164.3(3) . . . .
C14 C13 C17 C16 -43.5(3) . . . .
C14 C13 C17 C18 73.9(3) . . . .
C14 C15 C16 C17 2.6(3) . . . .
C15 C16 C17 O2 144.6(3) . . . .
C15 C16 C17 C13 25.7(3) . . . .
C15 C16 C17 C18 -93.9(3) . . . .
C17 C13 C14 C8 176.1(2) . . . .
C17 C13 C14 C15 46.1(3) . . . .
C20 C6 C7 C8 65.2(3) . . . .
C20 C6 C7 C11 -63.3(3) . . . .
C21 C13 C14 C8 61.0(3) . . . .
C21 C13 C14 C15 -69.0(3) . . . .
C21 C13 C17 O2 -45.5(4) . . . .
C21 C13 C17 C16 75.2(3) . . . .
C21 C13 C17 C18 -167.3(3) . . . .
