#------------------------------------------------------------------------------
#$Date: 2022-05-03 01:27:48 +0300 (Tue, 03 May 2022) $
#$Revision: 274809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566899.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_1566899
loop_
_publ_author_name
'Zhang, Qi'
'Chiou, Mong-Feng'
'Ye, Changqing'
'Yuan, Xiaobin'
'Li, Yajun'
'Bao, Hongli'
_publ_section_title
;
 Radical 1,2,3-Tricarbofunctionalization of α-Vinyl-β-Ketoesters Enabled
 by Carbon Shift from All-carbon Quaternary Center
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00902A
_journal_year                    2022
_chemical_formula_moiety         'C22 H17 F3 O3'
_chemical_formula_sum            'C22 H17 F3 O3'
_chemical_formula_weight         386.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-09-04
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-09-08 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.403(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6118(11)
_cell_length_b                   9.7486(8)
_cell_length_c                   17.4474(16)
_cell_measurement_reflns_used    13440
_cell_measurement_temperature    290.00(14)
_cell_measurement_theta_max      60.5890
_cell_measurement_theta_min      4.5290
_cell_volume                     1928.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00  87.00   0.50    0.20    --   72.03  57.00   0.00   52
  2  ω     96.00 139.00   0.50    0.20    --   72.03  57.00   0.00   86
  3  ω     81.00 143.00   0.50    0.20    --   72.03 125.00  90.00  124
  4  ω     91.00 121.00   0.50    0.20    --   72.03  93.00  75.00   60
  5  ω     49.00 103.00   0.50    0.20    --   72.03 -93.00 -36.00  108
  6  ω     21.00 106.00   0.50    0.20    --   72.03-125.00 -60.00  170
  7  ω     27.00  53.00   0.50    0.20    --   72.03-125.00-180.00   52
  8  ω     56.00  86.00   0.50    0.20    --   72.03-125.00-180.00   60
  9  ω     21.00  47.00   0.50    0.20    --   72.03 -93.00 -36.00   52
 10  ω     30.00  94.00   0.50    0.20    --   72.03 -77.00  30.00  128
 11  ω      0.00  43.00   0.50    0.20    --   72.03 -38.00 120.00   86
 12  ω     -3.00  22.00   0.50    0.20    --   72.03 -19.00 120.00   50
 13  ω     -3.00  26.00   0.50    0.20    --   72.03 -19.00  30.00   58
 14  ω     -3.00  25.00   0.50    0.20    --   72.03 -19.00   0.00   56
 15  ω     -2.00  26.00   0.50    0.20    --   72.03 -19.00 -30.00   56
 16  ω     -3.00  26.00   0.50    0.20    --   72.03 -19.00-120.00   58
 17  ω    -11.00  15.00   0.50    0.05    --   -1.72 -57.00-150.00   52
 18  ω    -29.00  11.00   0.50    0.05    --   -1.72 -93.00 -36.00   80
 19  ω    -69.00 -43.00   0.50    0.05    --   -1.72 -57.00-150.00   52
 20  ω   -112.00 -85.00   0.50    0.20    --  -75.46 -93.00 -36.00   54
 21  ω    -26.00  -1.00   0.50    0.20    --  -75.46  19.00 -90.00   50
 22  ω    -66.00 -16.00   0.50    0.20    --  -75.46  57.00-180.00  100
 23  ω    -98.00 -30.00   0.50    0.20    --  -75.46  77.00-150.00  136
 24  ω    -30.00  -5.00   0.50    0.20    --  -75.46  38.00 -90.00   50
 25  ω    -52.00  -7.00   0.50    0.20    --  -75.46  57.00 -60.00   90
 26  ω    -62.00  -7.00   0.50    0.20    --  -75.46  57.00   0.00  110
 27  ω    -42.00  -6.00   0.50    0.20    --  -75.46  38.00  60.00   72
 28  ω    -43.00  -5.00   0.50    0.20    --  -75.46  38.00 120.00   76
 29  ω     40.00  71.00   0.50    0.05    --   -1.72  57.00 -30.00   62
 30  ω    -12.00  22.00   0.50    0.05    --   -1.72  57.00 -30.00   68
 31  ω    -25.00   0.00   0.50    0.20    --  -75.46  19.00-150.00   50
 32  ω    -26.00  -1.00   0.50    0.20    --  -75.46  19.00-180.00   50
 33  ω   -106.00 -23.00   0.50    0.20    --  -75.46 125.00-180.00  166
 34  ω   -109.00 -23.00   0.50    0.20    --  -75.46 125.00   0.00  172
 35  ω    -42.00 -15.00   0.50    0.20    --  -75.46  93.00  75.00   54
 36  ω    -72.00 -46.00   0.50    0.20    --  -75.46  93.00  75.00   52
 37  ω    -32.00  30.00   0.50    0.05    --   -1.72  93.00  75.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328709000
_diffrn_orient_matrix_UB_12      -0.0664310000
_diffrn_orient_matrix_UB_13      0.0683808000
_diffrn_orient_matrix_UB_21      -0.0915393000
_diffrn_orient_matrix_UB_22      0.0545625000
_diffrn_orient_matrix_UB_23      0.0245799000
_diffrn_orient_matrix_UB_31      -0.0670013000
_diffrn_orient_matrix_UB_32      -0.1071946000
_diffrn_orient_matrix_UB_33      -0.0298906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28814
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.591
_diffrn_reflns_theta_min         4.512
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0759P)²+0.4678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3265
_reflns_number_total             4396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00902a3.cif
_cod_data_source_block           zq-5-120
_cod_database_code               1566899
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_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 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C8(H8), C25(H25), C7(H7), C23(H23), C26(H26), C27(H27),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 1.932
_oxdiff_exptl_absorpt_empirical_full_min 0.645
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O21 O 0.44317(15) 0.22979(13) 0.66641(8) 0.0676(4) Uani 1 1 d . . . . .
O22 O 0.51339(13) 0.38400(14) 0.84557(7) 0.0628(4) Uani 1 1 d . . . . .
O19 O 0.41467(15) 0.30211(14) 0.54301(7) 0.0709(4) Uani 1 1 d . . . . .
F18 F 0.28923(16) 0.5358(3) 0.85802(10) 0.1269(7) Uani 1 1 d . . . . .
C1 C 0.51565(16) 0.43276(16) 0.78187(10) 0.0481(4) Uani 1 1 d . . . . .
C3 C 0.40940(16) 0.47031(17) 0.63989(10) 0.0482(4) Uani 1 1 d . . . . .
F16 F 0.17075(17) 0.5925(2) 0.75385(12) 0.1264(7) Uani 1 1 d . . . . .
C10 C 0.62865(16) 0.45122(17) 0.75670(10) 0.0510(4) Uani 1 1 d . . . . .
C11 C 0.42333(16) 0.31995(17) 0.61906(10) 0.0494(4) Uani 1 1 d . . . . .
C12 C 0.30365(18) 0.53236(19) 0.59067(11) 0.0574(5) Uani 1 1 d . . . . .
C13 C 0.2192(2) 0.5935(2) 0.55665(12) 0.0630(5) Uani 1 1 d . . . . .
C2 C 0.40226(15) 0.48009(18) 0.72728(9) 0.0480(4) Uani 1 1 d . . . . .
H2 H 0.393240 0.577572 0.738395 0.058 Uiso 1 1 calc R U . . .
F17 F 0.14124(16) 0.4120(2) 0.81183(13) 0.1377(8) Uani 1 1 d . . . . .
C4 C 0.51911(18) 0.55096(19) 0.62837(11) 0.0564(5) Uani 1 1 d . . . . .
H4A H 0.527809 0.539321 0.574690 0.068 Uiso 1 1 calc R U . . .
H4B H 0.506958 0.647824 0.636600 0.068 Uiso 1 1 calc R U . . .
C5 C 0.63040(17) 0.50572(18) 0.68300(11) 0.0553(4) Uani 1 1 d . . . . .
C24 C 0.11633(19) 0.6676(2) 0.51828(12) 0.0633(5) Uani 1 1 d . . . . .
C9 C 0.73320(18) 0.4112(2) 0.80700(13) 0.0664(5) Uani 1 1 d . . . . .
H9 H 0.731138 0.373416 0.855625 0.080 Uiso 1 1 calc R U . . .
C14 C 0.29387(17) 0.4066(2) 0.74506(12) 0.0611(5) Uani 1 1 d . . . . .
H14A H 0.241661 0.382256 0.695715 0.073 Uiso 1 1 calc R U . . .
H14B H 0.319700 0.321985 0.772719 0.073 Uiso 1 1 calc R U . . .
C6 C 0.7391(2) 0.5195(3) 0.66200(15) 0.0792(7) Uani 1 1 d . . . . .
H6 H 0.742483 0.554612 0.612962 0.095 Uiso 1 1 calc R U . . .
C15 C 0.2263(2) 0.4866(3) 0.79210(14) 0.0783(7) Uani 1 1 d . . . . .
C8 C 0.8392(2) 0.4271(3) 0.78539(18) 0.0857(7) Uani 1 1 d . . . . .
H8 H 0.908955 0.401168 0.819376 0.103 Uiso 1 1 calc R U . . .
C25 C 0.0160(2) 0.6687(3) 0.54873(16) 0.0878(7) Uani 1 1 d . . . . .
H25 H 0.015280 0.620346 0.594595 0.105 Uiso 1 1 calc R U . . .
C20 C 0.4340(3) 0.1635(2) 0.51828(14) 0.0901(8) Uani 1 1 d . . . . .
H20A H 0.425268 0.161375 0.462317 0.135 Uiso 1 1 calc R U . . .
H20B H 0.377376 0.102969 0.533183 0.135 Uiso 1 1 calc R U . . .
H20C H 0.512154 0.134420 0.542979 0.135 Uiso 1 1 calc R U . . .
C7 C 0.8416(2) 0.4815(3) 0.71331(19) 0.0968(9) Uani 1 1 d . . . . .
H7 H 0.913575 0.492975 0.698829 0.116 Uiso 1 1 calc R U . . .
C23 C 0.1132(3) 0.7369(3) 0.44925(18) 0.1039(10) Uani 1 1 d . . . . .
H23 H 0.179271 0.737646 0.427134 0.125 Uiso 1 1 calc R U . . .
C26 C -0.0828(2) 0.7397(3) 0.51252(18) 0.0973(9) Uani 1 1 d . . . . .
H26 H -0.148852 0.740677 0.534642 0.117 Uiso 1 1 calc R U . . .
C27 C -0.0847(3) 0.8083(3) 0.4449(2) 0.1041(10) Uani 1 1 d . . . . .
H27 H -0.151540 0.857008 0.420655 0.125 Uiso 1 1 calc R U . . .
C28 C 0.0119(3) 0.8054(4) 0.4126(2) 0.1308(14) Uani 1 1 d . . . . .
H28 H 0.009943 0.850089 0.365197 0.157 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 0.0147 0.0070 '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'
F F 0.0599 0.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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 O19 C20 116.00(15) . . ?
O22 C1 C10 120.90(17) . . ?
O22 C1 C2 120.39(16) . . ?
C10 C1 C2 118.69(14) . . ?
C11 C3 C2 108.93(13) . . ?
C11 C3 C4 108.95(14) . . ?
C12 C3 C11 111.97(15) . . ?
C12 C3 C2 109.62(14) . . ?
C12 C3 C4 108.85(14) . . ?
C4 C3 C2 108.46(14) . . ?
C5 C10 C1 120.57(16) . . ?
C9 C10 C1 119.15(17) . . ?
C9 C10 C5 120.27(18) . . ?
O21 C11 O19 124.05(16) . . ?
O21 C11 C3 123.81(15) . . ?
O19 C11 C3 112.11(14) . . ?
C13 C12 C3 173.0(2) . . ?
C12 C13 C24 178.0(2) . . ?
C1 C2 C3 112.08(13) . . ?
C1 C2 H2 106.6 . . ?
C1 C2 C14 111.62(14) . . ?
C3 C2 H2 106.6 . . ?
C14 C2 C3 112.93(15) . . ?
C14 C2 H2 106.6 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.94(14) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C10 C5 C4 121.14(16) . . ?
C6 C5 C10 118.2(2) . . ?
C6 C5 C4 120.69(18) . . ?
C25 C24 C13 120.8(2) . . ?
C23 C24 C13 121.3(2) . . ?
C23 C24 C25 117.9(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C2 C14 H14A 108.5 . . ?
C2 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C2 114.98(19) . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
F18 C15 F16 106.1(3) . . ?
F18 C15 F17 106.1(2) . . ?
F18 C15 C14 114.73(19) . . ?
F16 C15 F17 104.4(2) . . ?
F16 C15 C14 113.2(2) . . ?
F17 C15 C14 111.6(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.3 . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.2(2) . . ?
C26 C25 H25 119.4 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C24 C23 H23 119.9 . . ?
C24 C23 C28 120.2(3) . . ?
C28 C23 H23 119.9 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
C28 C27 H27 120.3 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.9(3) . . ?
C27 C28 H28 119.6 . . ?
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
O21 C11 1.194(2) . ?
O22 C1 1.214(2) . ?
O19 C11 1.321(2) . ?
O19 C20 1.450(2) . ?
F18 C15 1.314(3) . ?
C1 C10 1.481(2) . ?
C1 C2 1.521(2) . ?
C3 C11 1.527(2) . ?
C3 C12 1.469(3) . ?
C3 C2 1.548(2) . ?
C3 C4 1.547(2) . ?
F16 C15 1.320(3) . ?
C10 C5 1.395(3) . ?
C10 C9 1.392(3) . ?
C12 C13 1.191(3) . ?
C13 C24 1.433(3) . ?
C2 H2 0.9800 . ?
C2 C14 1.537(2) . ?
F17 C15 1.330(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.498(3) . ?
C5 C6 1.395(3) . ?
C24 C25 1.381(3) . ?
C24 C23 1.374(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.372(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.474(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.371(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C7 H7 0.9300 . ?
C23 H23 0.9300 . ?
C23 C28 1.384(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.353(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.360(5) . ?
C28 H28 0.9300 . ?
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
O22 C1 C10 C5 179.19(16) . . . . ?
O22 C1 C10 C9 0.3(3) . . . . ?
O22 C1 C2 C3 -151.70(16) . . . . ?
O22 C1 C2 C14 -23.9(2) . . . . ?
C1 C10 C5 C4 1.9(3) . . . . ?
C1 C10 C5 C6 -179.33(18) . . . . ?
C1 C10 C9 C8 -179.9(2) . . . . ?
C1 C2 C14 C15 100.2(2) . . . . ?
C3 C2 C14 C15 -132.49(18) . . . . ?
C3 C4 C5 C10 -28.9(2) . . . . ?
C3 C4 C5 C6 152.38(19) . . . . ?
C10 C1 C2 C3 30.1(2) . . . . ?
C10 C1 C2 C14 157.91(15) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C10 C9 C8 C7 -0.7(4) . . . . ?
C11 C3 C2 C1 63.89(18) . . . . ?
C11 C3 C2 C14 -63.21(19) . . . . ?
C11 C3 C4 C5 -64.22(19) . . . . ?
C12 C3 C11 O21 -131.6(2) . . . . ?
C12 C3 C11 O19 50.4(2) . . . . ?
C12 C3 C2 C1 -173.28(14) . . . . ?
C12 C3 C2 C14 59.61(19) . . . . ?
C12 C3 C4 C5 173.42(15) . . . . ?
C13 C24 C25 C26 179.8(3) . . . . ?
C13 C24 C23 C28 178.7(3) . . . . ?
C2 C1 C10 C5 -2.6(2) . . . . ?
C2 C1 C10 C9 178.50(16) . . . . ?
C2 C3 C11 O21 -10.2(2) . . . . ?
C2 C3 C11 O19 171.80(15) . . . . ?
C2 C3 C4 C5 54.21(19) . . . . ?
C2 C14 C15 F18 -53.0(3) . . . . ?
C2 C14 C15 F16 68.9(3) . . . . ?
C2 C14 C15 F17 -173.70(19) . . . . ?
C4 C3 C11 O21 107.9(2) . . . . ?
C4 C3 C11 O19 -70.06(19) . . . . ?
C4 C3 C2 C1 -54.55(18) . . . . ?
C4 C3 C2 C14 178.34(14) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C5 C10 C9 C8 1.2(3) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C24 C25 C26 C27 1.4(5) . . . . ?
C24 C23 C28 C27 1.6(6) . . . . ?
C9 C10 C5 C4 -179.26(17) . . . . ?
C9 C10 C5 C6 -0.5(3) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
C25 C24 C23 C28 0.3(5) . . . . ?
C25 C26 C27 C28 0.5(6) . . . . ?
C20 O19 C11 O21 -1.6(3) . . . . ?
C20 O19 C11 C3 176.35(19) . . . . ?
C23 C24 C25 C26 -1.8(4) . . . . ?
C26 C27 C28 C23 -2.0(7) . . . . ?
