#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:51:27 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287308 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/99/1569908.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_1569908
loop_
_publ_author_name
'Jiang, Bo'
'Gui, Wu-Tao'
'Wang, Hao-Tian'
'Xie, Ke'
'Chen, Zhi-Chao'
'Zhu, Lei'
'Ouyang, Qin'
'Du, Wei'
'Chen, Ying-Chun'
_publ_section_title
;
 Asymmetric Friedel-Crafts reaction of unsaturated carbonyl-tethered
 heteroarenes via vinylogous activation of
 Pd⁰-π-Lewis base catalysis.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10867
_journal_page_last               10874
_journal_paper_doi               10.1039/d3sc03996j
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H27 F N2 O3 S'
_chemical_formula_sum            'C32 H27 F N2 O3 S'
_chemical_formula_weight         538.61
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-27 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                106.668(2)
_cell_angle_beta                 101.698(2)
_cell_angle_gamma                117.979(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2530(5)
_cell_length_b                   9.3566(5)
_cell_length_c                   9.9037(6)
_cell_measurement_reflns_used    7730
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.506
_cell_measurement_theta_min      2.341
_cell_volume                     665.24(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0484
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19634
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_min         2.341
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1113 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.8826.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6078
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0386
_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)+(0.0466P)²+0.0310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                5129
_reflns_number_total             6078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03996j2.cif
_cod_data_source_block           9f
_cod_depositor_comments
'Adding full bibliography for 1569903--1569908.cif.'
_cod_database_code               1569908
_shelx_shelxl_version_number     2014/7
_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_max   0.972
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.86 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C32(H32), C6(H6), C7(H7), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, 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
S1 S 0.67110(9) 0.87058(9) 0.64744(7) 0.04581(19) Uani 1 1 d . . . . .
F1 F 0.5936(4) 0.0622(4) 1.0553(3) 0.0890(7) Uani 1 1 d . . . . .
O2 O 0.6001(4) 0.7994(3) 0.7461(3) 0.0627(6) Uani 1 1 d . . . . .
O3 O 0.0518(3) -0.0078(3) 0.4994(3) 0.0624(6) Uani 1 1 d . . . . .
O4 O 0.8155(3) 1.0555(3) 0.7089(3) 0.0620(6) Uani 1 1 d . . . . .
C1 C 0.3156(4) 0.3186(4) 0.2934(3) 0.0385(6) Uani 1 1 d . . . . .
N2 N 0.7425(3) 0.7547(3) 0.5689(3) 0.0406(5) Uani 1 1 d D . . . .
C3 C 0.7536(4) 0.4905(4) 0.5207(3) 0.0394(6) Uani 1 1 d . . . . .
C33 C 0.5026(5) 0.0729(5) 0.9364(4) 0.0621(9) Uani 1 1 d . . . . .
C2 C 0.3241(6) -0.0517(7) 0.8609(5) 0.0869(14) Uani 1 1 d . . . . .
H2A H 0.2649 -0.1409 0.8910 0.104 Uiso 1 1 calc R U . . .
C32 C 0.2335(5) -0.0429(6) 0.7394(5) 0.0773(12) Uani 1 1 d . . . . .
H32 H 0.1106 -0.1256 0.6884 0.093 Uiso 1 1 calc R U . . .
C4 C 0.3192(4) 0.0848(4) 0.6907(3) 0.0421(6) Uani 1 1 d . . . . .
C5 C 0.2150(4) 0.0848(4) 0.5542(3) 0.0423(6) Uani 1 1 d . . . . .
C6 C 0.3140(4) 0.1959(4) 0.4843(3) 0.0431(6) Uani 1 1 d . . . . .
H6 H 0.4372 0.2541 0.5206 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2325(4) 0.2155(4) 0.3709(3) 0.0415(6) Uani 1 1 d . . . . .
H7 H 0.1094 0.1568 0.3383 0.050 Uiso 1 1 calc R U . . .
C8 C 0.4904(3) 0.4640(3) 0.3431(3) 0.0367(6) Uani 1 1 d . . . . .
C9 C 0.6317(3) 0.5568(4) 0.5028(3) 0.0372(6) Uani 1 1 d . . . . .
H9 H 0.5673 0.5273 0.5686 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4930(4) 0.8306(4) 0.5007(3) 0.0428(6) Uani 1 1 d . . . . .
C11 C 0.5315(5) 0.9226(5) 0.4121(4) 0.0539(8) Uani 1 1 d . . . . .
H11 H 0.6494 1.0070 0.4327 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3947(5) 0.8889(5) 0.2933(4) 0.0597(8) Uani 1 1 d . . . . .
H12 H 0.4216 0.9519 0.2346 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2197(4) 0.7645(5) 0.2598(4) 0.0548(8) Uani 1 1 d . . . . .
C14 C 0.0711(6) 0.7311(7) 0.1316(5) 0.0843(13) Uani 1 1 d . . . . .
H14A H 0.1205 0.8093 0.0850 0.126 Uiso 1 1 calc R U . . .
H14B H -0.0053 0.7550 0.1720 0.126 Uiso 1 1 calc R U . . .
H14C H 0.0032 0.6078 0.0559 0.126 Uiso 1 1 calc R U . . .
C15 C 0.3188(4) 0.7060(4) 0.4690(4) 0.0553(8) Uani 1 1 d . . . . .
H15 H 0.2914 0.6431 0.5278 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1848(5) 0.6750(5) 0.3493(5) 0.0652(9) Uani 1 1 d . . . . .
H16 H 0.0668 0.5905 0.3284 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5920(5) 0.1978(6) 0.8935(5) 0.0754(11) Uani 1 1 d . . . . .
H17 H 0.7149 0.2799 0.9458 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4992(5) 0.2039(5) 0.7694(5) 0.0680(10) Uani 1 1 d . . . . .
H18 H 0.5612 0.2916 0.7389 0.082 Uiso 1 1 calc R U . . .
N19 N 0.2170(3) 0.2823(3) 0.1482(3) 0.0457(6) Uani 1 1 d . . . . .
C20 C 0.0309(5) 0.1378(6) 0.0542(4) 0.0699(10) Uani 1 1 d . . . . .
H20A H -0.0433 0.1695 0.0909 0.105 Uiso 1 1 calc R U . . .
H20B H 0.0077 0.0289 0.0602 0.105 Uiso 1 1 calc R U . . .
H20C H 0.0050 0.1192 -0.0506 0.105 Uiso 1 1 calc R U . . .
C21 C 0.3261(4) 0.4006(4) 0.1022(3) 0.0434(6) Uani 1 1 d . . . . .
C22 C 0.2845(5) 0.4153(5) -0.0350(4) 0.0547(8) Uani 1 1 d . . . . .
H22 H 0.1698 0.3376 -0.1119 0.066 Uiso 1 1 calc R U . . .
C23 C 0.4178(5) 0.5474(5) -0.0519(4) 0.0630(9) Uani 1 1 d . . . . .
H23 H 0.3934 0.5612 -0.1413 0.076 Uiso 1 1 calc R U . . .
C24 C 0.5914(5) 0.6633(5) 0.0631(4) 0.0632(9) Uani 1 1 d . . . . .
H24 H 0.6802 0.7509 0.0473 0.076 Uiso 1 1 calc R U . . .
C25 C 0.6337(5) 0.6503(5) 0.1986(4) 0.0528(7) Uani 1 1 d . . . . .
H25 H 0.7492 0.7283 0.2741 0.063 Uiso 1 1 calc R U . . .
C26 C 0.4980(4) 0.5162(4) 0.2208(3) 0.0404(6) Uani 1 1 d . . . . .
C27 C 0.7623(4) 0.3859(4) 0.3969(4) 0.0509(7) Uani 1 1 d . . . . .
H27 H 0.6948 0.3561 0.2977 0.061 Uiso 1 1 calc R U . . .
C28 C 0.8714(5) 0.3245(5) 0.4196(4) 0.0610(9) Uani 1 1 d . . . . .
H28 H 0.8775 0.2552 0.3352 0.073 Uiso 1 1 calc R U . . .
C29 C 0.9702(5) 0.3648(5) 0.5645(5) 0.0605(9) Uani 1 1 d . . . . .
H29 H 1.0436 0.3238 0.5787 0.073 Uiso 1 1 calc R U . . .
C30 C 0.9600(5) 0.4664(5) 0.6887(4) 0.0631(9) Uani 1 1 d . . . . .
H30 H 1.0244 0.4917 0.7873 0.076 Uiso 1 1 calc R U . . .
C31 C 0.8541(4) 0.5315(4) 0.6676(4) 0.0539(8) Uani 1 1 d . . . . .
H31 H 0.8504 0.6030 0.7524 0.065 Uiso 1 1 calc R U . . .
H2 H 0.812(4) 0.802(4) 0.527(3) 0.051(9) Uiso 1 1 d 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
O2 S1 N2 107.06(13) . . ?
O2 S1 C10 107.48(15) . . ?
O4 S1 O2 120.41(15) . . ?
O4 S1 N2 105.51(14) . . ?
O4 S1 C10 107.95(13) . . ?
N2 S1 C10 107.89(12) . . ?
C8 C1 C7 130.1(2) . . ?
N19 C1 C7 120.6(2) . . ?
N19 C1 C8 109.2(2) . . ?
S1 N2 H2 115(2) . . ?
C9 N2 S1 120.37(18) . . ?
C9 N2 H2 117(2) . . ?
C27 C3 C9 122.7(3) . . ?
C27 C3 C31 118.8(3) . . ?
C31 C3 C9 118.5(3) . . ?
C2 C33 F1 118.4(3) . . ?
C17 C33 F1 119.1(4) . . ?
C17 C33 C2 122.4(4) . . ?
C33 C2 H2A 120.9 . . ?
C33 C2 C32 118.3(4) . . ?
C32 C2 H2A 120.9 . . ?
C2 C32 H32 119.1 . . ?
C2 C32 C4 121.8(4) . . ?
C4 C32 H32 119.1 . . ?
C32 C4 C5 119.6(3) . . ?
C18 C4 C32 117.1(3) . . ?
C18 C4 C5 123.2(3) . . ?
O3 C5 C4 121.1(3) . . ?
O3 C5 C6 120.7(3) . . ?
C6 C5 C4 118.3(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.1(3) . . ?
C7 C6 H6 119.0 . . ?
C1 C7 H7 116.7 . . ?
C6 C7 C1 126.6(2) . . ?
C6 C7 H7 116.7 . . ?
C1 C8 C9 124.6(2) . . ?
C1 C8 C26 106.3(2) . . ?
C26 C8 C9 128.7(2) . . ?
N2 C9 C3 108.8(2) . . ?
N2 C9 C8 114.6(2) . . ?
N2 C9 H9 105.9 . . ?
C3 C9 H9 105.9 . . ?
C8 C9 C3 114.8(2) . . ?
C8 C9 H9 105.9 . . ?
C11 C10 S1 118.7(2) . . ?
C15 C10 S1 121.5(2) . . ?
C15 C10 C11 119.7(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 C16 117.8(3) . . ?
C16 C13 C14 121.2(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15 120.4 . . ?
C10 C15 C16 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C13 C16 C15 122.2(3) . . ?
C13 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C33 C17 H17 120.6 . . ?
C33 C17 C18 118.7(4) . . ?
C18 C17 H17 120.6 . . ?
C4 C18 C17 121.7(3) . . ?
C4 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C1 N19 C20 126.5(3) . . ?
C21 N19 C1 108.9(2) . . ?
C21 N19 C20 124.5(3) . . ?
N19 C20 H20A 109.5 . . ?
N19 C20 H20B 109.5 . . ?
N19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N19 C21 C22 129.1(3) . . ?
N19 C21 C26 108.3(2) . . ?
C22 C21 C26 122.6(3) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 C21 117.6(3) . . ?
C23 C22 H22 121.2 . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.3(3) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.6(3) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C8 107.3(2) . . ?
C21 C26 C25 118.3(3) . . ?
C25 C26 C8 134.5(3) . . ?
C3 C27 H27 119.9 . . ?
C3 C27 C28 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.3 . . ?
C28 C29 C30 119.4(3) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.3(3) . . ?
C31 C30 H30 119.8 . . ?
C3 C31 H31 119.8 . . ?
C30 C31 C3 120.4(3) . . ?
C30 C31 H31 119.8 . . ?
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
S1 O2 1.433(2) . ?
S1 O4 1.431(2) . ?
S1 N2 1.616(2) . ?
S1 C10 1.763(3) . ?
F1 C33 1.359(4) . ?
O3 C5 1.223(4) . ?
C1 C7 1.442(4) . ?
C1 C8 1.392(4) . ?
C1 N19 1.383(3) . ?
N2 C9 1.470(3) . ?
N2 H2 0.854(14) . ?
C3 C9 1.525(4) . ?
C3 C27 1.376(4) . ?
C3 C31 1.388(4) . ?
C33 C2 1.356(6) . ?
C33 C17 1.324(5) . ?
C2 H2A 0.9300 . ?
C2 C32 1.368(6) . ?
C32 H32 0.9300 . ?
C32 C4 1.373(4) . ?
C4 C5 1.493(4) . ?
C4 C18 1.363(5) . ?
C5 C6 1.475(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.329(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.508(4) . ?
C8 C26 1.432(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.382(4) . ?
C10 C15 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(5) . ?
C13 C14 1.504(5) . ?
C13 C16 1.371(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.377(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.382(5) . ?
C18 H18 0.9300 . ?
N19 C20 1.451(4) . ?
N19 C21 1.370(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.400(4) . ?
C21 C26 1.407(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.359(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.403(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.377(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.411(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.387(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.368(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.373(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.387(5) . ?
C31 H31 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
S1 N2 C9 C3 -148.38(19) . . . . ?
S1 N2 C9 C8 81.6(3) . . . . ?
S1 C10 C11 C12 177.7(3) . . . . ?
S1 C10 C15 C16 -177.5(3) . . . . ?
F1 C33 C2 C32 -178.7(4) . . . . ?
F1 C33 C17 C18 177.9(4) . . . . ?
O2 S1 N2 C9 46.4(2) . . . . ?
O2 S1 C10 C11 164.8(2) . . . . ?
O2 S1 C10 C15 -17.8(3) . . . . ?
O3 C5 C6 C7 7.3(4) . . . . ?
O4 S1 N2 C9 175.7(2) . . . . ?
O4 S1 C10 C11 33.5(3) . . . . ?
O4 S1 C10 C15 -149.1(3) . . . . ?
C1 C8 C9 N2 -137.2(3) . . . . ?
C1 C8 C9 C3 95.8(3) . . . . ?
C1 C8 C26 C21 0.6(3) . . . . ?
C1 C8 C26 C25 -179.5(3) . . . . ?
C1 N19 C21 C22 -179.5(3) . . . . ?
C1 N19 C21 C26 -0.4(3) . . . . ?
N2 S1 C10 C11 -80.0(3) . . . . ?
N2 S1 C10 C15 97.3(3) . . . . ?
C3 C27 C28 C29 0.8(5) . . . . ?
C33 C2 C32 C4 1.7(8) . . . . ?
C33 C17 C18 C4 -0.2(7) . . . . ?
C2 C33 C17 C18 1.6(7) . . . . ?
C2 C32 C4 C5 178.0(4) . . . . ?
C2 C32 C4 C18 -0.4(6) . . . . ?
C32 C4 C5 O3 11.6(5) . . . . ?
C32 C4 C5 C6 -166.9(3) . . . . ?
C32 C4 C18 C17 -0.3(6) . . . . ?
C4 C5 C6 C7 -174.2(3) . . . . ?
C5 C4 C18 C17 -178.7(4) . . . . ?
C5 C6 C7 C1 -179.2(3) . . . . ?
C7 C1 C8 C9 -5.5(4) . . . . ?
C7 C1 C8 C26 -178.7(3) . . . . ?
C7 C1 N19 C20 -4.0(5) . . . . ?
C7 C1 N19 C21 178.9(2) . . . . ?
C8 C1 C7 C6 -24.2(5) . . . . ?
C8 C1 N19 C20 177.9(3) . . . . ?
C8 C1 N19 C21 0.8(3) . . . . ?
C9 C3 C27 C28 -178.0(3) . . . . ?
C9 C3 C31 C30 176.8(3) . . . . ?
C9 C8 C26 C21 -172.3(3) . . . . ?
C9 C8 C26 C25 7.6(5) . . . . ?
C10 S1 N2 C9 -69.1(2) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C10 C15 C16 C13 0.2(5) . . . . ?
C11 C10 C15 C16 -0.2(5) . . . . ?
C11 C12 C13 C14 178.9(4) . . . . ?
C11 C12 C13 C16 0.4(5) . . . . ?
C12 C13 C16 C15 -0.3(5) . . . . ?
C14 C13 C16 C15 -178.7(4) . . . . ?
C15 C10 C11 C12 0.3(5) . . . . ?
C17 C33 C2 C32 -2.3(7) . . . . ?
C18 C4 C5 O3 -170.1(4) . . . . ?
C18 C4 C5 C6 11.4(4) . . . . ?
N19 C1 C7 C6 158.1(3) . . . . ?
N19 C1 C8 C9 172.4(2) . . . . ?
N19 C1 C8 C26 -0.8(3) . . . . ?
N19 C21 C22 C23 179.0(3) . . . . ?
N19 C21 C26 C8 -0.1(3) . . . . ?
N19 C21 C26 C25 180.0(3) . . . . ?
C20 N19 C21 C22 3.4(5) . . . . ?
C20 N19 C21 C26 -177.6(3) . . . . ?
C21 C22 C23 C24 0.9(5) . . . . ?
C22 C21 C26 C8 179.0(3) . . . . ?
C22 C21 C26 C25 -0.9(4) . . . . ?
C22 C23 C24 C25 -1.1(6) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C24 C25 C26 C8 -179.2(3) . . . . ?
C24 C25 C26 C21 0.7(5) . . . . ?
C26 C8 C9 N2 34.5(4) . . . . ?
C26 C8 C9 C3 -92.5(3) . . . . ?
C26 C21 C22 C23 0.1(5) . . . . ?
C27 C3 C9 N2 -115.8(3) . . . . ?
C27 C3 C9 C8 14.2(4) . . . . ?
C27 C3 C31 C30 -0.6(5) . . . . ?
C27 C28 C29 C30 0.4(5) . . . . ?
C28 C29 C30 C31 -1.7(5) . . . . ?
C29 C30 C31 C3 1.8(5) . . . . ?
C31 C3 C9 N2 66.9(3) . . . . ?
C31 C3 C9 C8 -163.1(3) . . . . ?
C31 C3 C27 C28 -0.7(4) . . . . ?
