#------------------------------------------------------------------------------
#$Date: 2024-06-28 12:32:51 +0300 (Fri, 28 Jun 2024) $
#$Revision: 292638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129182.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_7129182
loop_
_publ_author_name
'Dong, Jinhuan'
'Feng, Wanzhong'
'Wang, Lei'
'Li, Mei'
'Chen, Zhe'
'Xu, Xianxiu'
_publ_section_title
;
 Cu/Base Co-catalyzed [3 + 3] Cycloaddition for the Synthesis of Highly
 Functionalized 4-Fluoropyridines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05412K
_journal_year                    2021
_chemical_formula_moiety         'C18 H13 Cl F N O2 S'
_chemical_formula_sum            'C18 H13 Cl F N O2 S'
_chemical_formula_weight         361.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-09
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                96.689(6)
_cell_angle_beta                 101.847(6)
_cell_angle_gamma                99.853(5)
_cell_formula_units_Z            4
_cell_length_a                   8.5995(5)
_cell_length_b                   11.0868(7)
_cell_length_c                   18.5904(14)
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6730
_cell_measurement_theta_min      6.3290
_cell_volume                     1687.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9776
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  67.00   1.00    1.00    --    0.00  57.00-120.00   48
  2  ω     33.00  69.00   1.00    1.00    --    0.00  57.00 -60.00   36
  3  ω    -63.00 -27.00   1.00    1.00    --    0.00 -57.00 150.00   36
  4  ω    -16.00  21.00   1.00    1.00    --    0.00 -57.00 150.00   37
  5  ω     26.00 104.00   1.00    1.45    --   54.00-125.00-120.00   78
  6  ω    -18.00  75.00   1.00    1.45    --   54.00 -37.00  60.00   93
  7  ω     36.00  86.00   1.00    1.45    --   54.00-125.00  90.00   50
  8  ω     77.00 123.00   1.00    1.45    --   54.00  37.00-120.00   46
  9  ω     15.00  80.00   1.00    1.45    --   54.00 -37.00-150.00   65
 10  ω     29.00  57.00   1.00    1.45    --   54.00  37.00-120.00   28
 11  ω     30.00 126.00   1.00    1.45    --   54.00  37.00  30.00   96
 12  ω     79.00 106.00   1.00    1.45    --  108.00-111.00  90.00   27
 13  ω     65.00 112.00   1.00    1.45    --  108.00-111.00-180.00   47
 14  ω     93.00 171.00   1.00    1.45    --  108.00  77.00-120.00   78
 15  ω     63.00 129.00   1.00    1.45    --  108.00 -63.00 -90.00   66
 16  ω    102.00 178.00   1.00    1.45    --  108.00  37.00 -60.00   76
 17  ω     38.00  69.00   1.00    1.45    --  108.00 -77.00  30.00   31
 18  ω    131.00 175.00   1.00    1.45    --  108.00  63.00 -30.00   44
 19  ω     86.00 128.00   1.00    1.45    --  108.00  63.00 -30.00   42
 20  ω     44.00 142.00   1.00    1.45    --  108.00 -91.00-150.00   98
 21  ω    112.00 137.00   1.00    1.45    --  108.00 178.00 150.00   25
 22  ω     41.00  97.00   1.00    1.45    --  108.00 -50.00  90.00   56
 23  ω     85.00 111.00   1.00    1.45    --  108.00-111.00   0.00   26
 24  ω     66.00 102.00   1.00    1.45    --  108.00 178.00 150.00   36
 25  ω     83.00 120.00   1.00    1.45    --  108.00 178.00-180.00   37
 26  ω     91.00 116.00   1.00    1.45    --  108.00  63.00 120.00   25
 27  ω     38.00 128.00   1.00    1.45    --  108.00 -50.00-180.00   90
 28  ω     87.00 112.00   1.00    1.45    --  108.00 -77.00  30.00   25
 29  ω     87.00 166.00   1.00    1.45    --  108.00  37.00  30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0842983000
_diffrn_orient_matrix_UB_12      0.1311661000
_diffrn_orient_matrix_UB_13      -0.0066448000
_diffrn_orient_matrix_UB_21      -0.1040623000
_diffrn_orient_matrix_UB_22      -0.0137782000
_diffrn_orient_matrix_UB_23      -0.0796534000
_diffrn_orient_matrix_UB_31      -0.1302891000
_diffrn_orient_matrix_UB_32      0.0547775000
_diffrn_orient_matrix_UB_33      0.0310201000
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11108
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                4322
_reflns_number_total             6014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05412k2.cif
_cod_data_source_block           exp_3908
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H26 Cl2 F2 N2 O4 S2'
_cod_original_formula_weight         723.61
_cod_original_formula_moiety         '2(C18 H13 Cl F N O2 S)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1687.83(19)
_cod_database_code               7129182
_chemical_oxdiff_usercomment     CHNOCl
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Me refined with riding coordinates:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30),
  C33(H33), C34(H34), C36(H36), C37(H37)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.686
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6061(4) 0.1348(4) 0.89038(17) 0.0773(9) Uani 1 1 d . . .
C2 C 0.7393(5) 0.0931(5) 0.9271(2) 0.0975(13) Uani 1 1 d . . .
H2 H 0.8423 0.1431 0.9385 0.117 Uiso 1 1 calc R . .
C3 C 0.7156(5) -0.0249(5) 0.9465(2) 0.1030(14) Uani 1 1 d . . .
H3 H 0.8034 -0.0532 0.9722 0.124 Uiso 1 1 calc R . .
C4 C 0.5675(5) -0.0988(4) 0.9285(2) 0.0945(12) Uani 1 1 d . . .
H4 H 0.5538 -0.1783 0.9407 0.113 Uiso 1 1 calc R . .
C5 C 0.4355(4) -0.0562(3) 0.89185(18) 0.0742(9) Uani 1 1 d . . .
H5 H 0.3338 -0.1083 0.8793 0.089 Uiso 1 1 calc R . .
C6 C 0.4510(3) 0.0618(3) 0.87341(16) 0.0615(7) Uani 1 1 d . . .
C7 C 0.3070(3) 0.1045(3) 0.83364(15) 0.0552(7) Uani 1 1 d . . .
C8 C 0.2175(3) 0.0401(3) 0.76491(15) 0.0579(7) Uani 1 1 d . . .
H8 H 0.2508 -0.0297 0.7455 0.070 Uiso 1 1 calc R . .
C10 C 0.0423(3) 0.1711(2) 0.75396(15) 0.0497(6) Uani 1 1 d . . .
C11 C 0.1185(4) 0.2425(3) 0.82175(16) 0.0622(7) Uani 1 1 d . . .
H11 H 0.0830 0.3121 0.8399 0.075 Uiso 1 1 calc R . .
C12 C 0.2495(4) 0.2047(3) 0.86067(15) 0.0624(7) Uani 1 1 d . . .
C13 C -0.0693(3) 0.2359(2) 0.61496(16) 0.0502(6) Uani 1 1 d . . .
C14 C -0.0994(3) 0.1392(3) 0.55683(17) 0.0625(7) Uani 1 1 d . . .
H14 H -0.1535 0.0610 0.5609 0.075 Uiso 1 1 calc R . .
C15 C -0.0488(4) 0.1592(3) 0.49282(18) 0.0677(8) Uani 1 1 d . . .
H15 H -0.0701 0.0943 0.4534 0.081 Uiso 1 1 calc R . .
C16 C 0.0334(3) 0.2748(3) 0.48631(18) 0.0656(8) Uani 1 1 d . . .
C17 C 0.0624(4) 0.3696(3) 0.5446(2) 0.0693(9) Uani 1 1 d . . .
H17 H 0.1169 0.4476 0.5405 0.083 Uiso 1 1 calc R . .
C18 C 0.0128(3) 0.3522(3) 0.60945(18) 0.0609(7) Uani 1 1 d . . .
H18 H 0.0340 0.4174 0.6487 0.073 Uiso 1 1 calc R . .
C19 C 0.0904(4) 0.2951(4) 0.4160(2) 0.0935(13) Uani 1 1 d . . .
H19A H 0.0461 0.3609 0.3956 0.140 Uiso 1 1 calc R . .
H19B H 0.0547 0.2204 0.3804 0.140 Uiso 1 1 calc R . .
H19C H 0.2067 0.3170 0.4276 0.140 Uiso 1 1 calc R . .
C20 C -0.0407(4) 0.3625(3) 0.09838(17) 0.0701(8) Uani 1 1 d . . .
C21 C -0.1773(5) 0.4005(4) 0.0619(2) 0.0938(12) Uani 1 1 d . . .
H21 H -0.1892 0.4125 0.0126 0.113 Uiso 1 1 calc R . .
C22 C -0.2954(5) 0.4202(4) 0.0998(3) 0.0937(12) Uani 1 1 d . . .
H22 H -0.3880 0.4447 0.0756 0.112 Uiso 1 1 calc R . .
C23 C -0.2771(4) 0.4039(3) 0.1726(2) 0.0865(10) Uani 1 1 d . . .
H23 H -0.3565 0.4179 0.1980 0.104 Uiso 1 1 calc R . .
C24 C -0.1417(4) 0.3672(3) 0.20773(18) 0.0686(8) Uani 1 1 d . . .
H24 H -0.1306 0.3562 0.2572 0.082 Uiso 1 1 calc R . .
C25 C -0.0204(3) 0.3457(3) 0.17222(15) 0.0543(6) Uani 1 1 d . . .
C26 C 0.1284(3) 0.3115(2) 0.21386(14) 0.0497(6) Uani 1 1 d . . .
C27 C 0.2470(4) 0.4000(3) 0.26328(16) 0.0618(7) Uani 1 1 d . . .
H27 H 0.2316 0.4813 0.2681 0.074 Uiso 1 1 calc R . .
C29 C 0.4007(3) 0.2612(2) 0.29708(14) 0.0480(6) Uani 1 1 d . . .
C30 C 0.2929(3) 0.1630(2) 0.25033(15) 0.0543(6) Uani 1 1 d . . .
H30 H 0.3106 0.0823 0.2473 0.065 Uiso 1 1 calc R . .
C31 C 0.1574(3) 0.1927(2) 0.20862(15) 0.0523(6) Uani 1 1 d . . .
C32 C 0.5355(3) 0.2448(2) 0.44400(14) 0.0453(6) Uani 1 1 d . . .
C33 C 0.4519(3) 0.1397(3) 0.46340(16) 0.0562(7) Uani 1 1 d . . .
H33 H 0.4214 0.0653 0.4306 0.067 Uiso 1 1 calc R . .
C34 C 0.4148(3) 0.1476(3) 0.53263(17) 0.0608(7) Uani 1 1 d . . .
H34 H 0.3604 0.0771 0.5463 0.073 Uiso 1 1 calc R . .
C35 C 0.4565(3) 0.2573(3) 0.58186(15) 0.0531(7) Uani 1 1 d . . .
C36 C 0.5384(3) 0.3601(3) 0.56121(16) 0.0609(7) Uani 1 1 d . . .
H36 H 0.5677 0.4346 0.5939 0.073 Uiso 1 1 calc R . .
C37 C 0.5782(3) 0.3549(3) 0.49242(16) 0.0567(7) Uani 1 1 d . . .
H37 H 0.6334 0.4255 0.4791 0.068 Uiso 1 1 calc R . .
C38 C 0.4150(4) 0.2629(4) 0.65724(17) 0.0778(10) Uani 1 1 d . . .
H38A H 0.4906 0.2281 0.6901 0.117 Uiso 1 1 calc R . .
H38B H 0.3072 0.2165 0.6520 0.117 Uiso 1 1 calc R . .
H38C H 0.4209 0.3477 0.6776 0.117 Uiso 1 1 calc R . .
Cl1 Cl 0.63686(13) 0.28080(12) 0.86417(6) 0.1142(4) Uani 1 1 d . . .
Cl2 Cl 0.10794(14) 0.33843(12) 0.05114(5) 0.1049(4) Uani 1 1 d . . .
F1 F 0.0468(2) 0.10196(16) 0.16110(11) 0.0785(5) Uani 1 1 d . . .
F2 F 0.3257(3) 0.26965(19) 0.92897(10) 0.0915(6) Uani 1 1 d . . .
N1 N 0.0870(3) 0.0711(2) 0.72469(12) 0.0555(6) Uani 1 1 d . . .
N2 N 0.3816(3) 0.3773(2) 0.30446(14) 0.0606(6) Uani 1 1 d . . .
O3 O 0.7089(2) 0.3391(2) 0.35805(12) 0.0766(6) Uani 1 1 d . . .
O4 O 0.5973(3) 0.1121(2) 0.33251(12) 0.0772(7) Uani 1 1 d . . .
O5 O -0.2598(2) 0.10602(18) 0.68191(12) 0.0665(5) Uani 1 1 d . . .
O6 O -0.1479(3) 0.32762(19) 0.73445(12) 0.0701(6) Uani 1 1 d . . .
S1 S 0.58102(8) 0.23627(7) 0.35666(4) 0.0564(2) Uani 1 1 d . . .
S2 S -0.12953(8) 0.21188(6) 0.69741(4) 0.0539(2) 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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 C1 C6 121.5(4) . . ?
C2 C1 Cl1 118.5(3) . . ?
C6 C1 Cl1 120.0(3) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 122.3(3) . . ?
C5 C6 C1 117.3(3) . . ?
C5 C6 C7 120.4(3) . . ?
C8 C7 C6 120.1(3) . . ?
C12 C7 C6 124.7(3) . . ?
C12 C7 C8 115.2(3) . . ?
C7 C8 H8 117.6 . . ?
N1 C8 C7 124.8(3) . . ?
N1 C8 H8 117.6 . . ?
C11 C10 S2 120.0(2) . . ?
N1 C10 C11 125.2(2) . . ?
N1 C10 S2 114.8(2) . . ?
C10 C11 H11 122.1 . . ?
C12 C11 C10 115.8(3) . . ?
C12 C11 H11 122.1 . . ?
C11 C12 C7 122.9(3) . . ?
F2 C12 C7 119.0(3) . . ?
F2 C12 C11 118.1(3) . . ?
C14 C13 C18 120.4(3) . . ?
C14 C13 S2 120.3(2) . . ?
C18 C13 S2 119.3(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C19 120.3(3) . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 C19 120.9(3) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 H18 120.6 . . ?
C17 C18 C13 118.8(3) . . ?
C17 C18 H18 120.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 Cl2 119.3(3) . . ?
C25 C20 C21 121.0(3) . . ?
C25 C20 Cl2 119.7(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 118.9 . . ?
C23 C24 C25 122.2(3) . . ?
C25 C24 H24 118.9 . . ?
C20 C25 C26 122.2(3) . . ?
C24 C25 C20 117.6(3) . . ?
C24 C25 C26 120.2(3) . . ?
C27 C26 C25 120.5(2) . . ?
C31 C26 C25 124.1(3) . . ?
C31 C26 C27 115.3(2) . . ?
C26 C27 H27 117.6 . . ?
N2 C27 C26 124.7(3) . . ?
N2 C27 H27 117.6 . . ?
C30 C29 S1 120.5(2) . . ?
N2 C29 C30 125.2(2) . . ?
N2 C29 S1 114.3(2) . . ?
C29 C30 H30 122.3 . . ?
C31 C30 C29 115.3(2) . . ?
C31 C30 H30 122.3 . . ?
C30 C31 C26 122.8(3) . . ?
F1 C31 C26 118.3(2) . . ?
F1 C31 C30 118.9(2) . . ?
C33 C32 S1 119.1(2) . . ?
C37 C32 C33 120.3(2) . . ?
C37 C32 S1 120.5(2) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 C32 118.7(3) . . ?
C34 C33 H33 120.6 . . ?
C33 C34 H34 119.1 . . ?
C35 C34 C33 121.8(3) . . ?
C35 C34 H34 119.1 . . ?
C34 C35 C38 120.5(3) . . ?
C36 C35 C34 118.4(3) . . ?
C36 C35 C38 121.1(3) . . ?
C35 C36 H36 119.4 . . ?
C35 C36 C37 121.2(3) . . ?
C37 C36 H36 119.4 . . ?
C32 C37 C36 119.6(3) . . ?
C32 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C10 N1 C8 116.2(2) . . ?
C29 N2 C27 116.7(2) . . ?
C32 S1 C29 103.59(11) . . ?
O3 S1 C29 107.24(13) . . ?
O3 S1 C32 108.72(13) . . ?
O3 S1 O4 119.99(14) . . ?
O4 S1 C29 106.82(13) . . ?
O4 S1 C32 109.23(13) . . ?
C13 S2 C10 103.94(12) . . ?
O5 S2 C10 107.26(12) . . ?
O5 S2 C13 109.06(14) . . ?
O6 S2 C10 106.38(13) . . ?
O6 S2 C13 109.01(13) . . ?
O6 S2 O5 119.99(13) . . ?
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
C1 C2 1.388(5) . ?
C1 C6 1.390(4) . ?
C1 Cl1 1.738(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.345(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 C7 1.487(4) . ?
C7 C8 1.390(4) . ?
C7 C12 1.375(4) . ?
C8 H8 0.9300 . ?
C8 N1 1.335(3) . ?
C10 C11 1.377(4) . ?
C10 N1 1.328(3) . ?
C10 S2 1.788(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C12 F2 1.358(3) . ?
C13 C14 1.380(4) . ?
C13 C18 1.386(4) . ?
C13 S2 1.750(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 C17 1.370(5) . ?
C16 C19 1.514(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.388(4) . ?
C20 C25 1.386(4) . ?
C20 Cl2 1.732(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.366(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(4) . ?
C25 C26 1.487(4) . ?
C26 C27 1.382(4) . ?
C26 C31 1.378(4) . ?
C27 H27 0.9300 . ?
C27 N2 1.330(3) . ?
C29 C30 1.380(4) . ?
C29 N2 1.321(3) . ?
C29 S1 1.794(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(4) . ?
C31 F1 1.348(3) . ?
C32 C33 1.386(4) . ?
C32 C37 1.375(4) . ?
C32 S1 1.742(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.385(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.379(4) . ?
C35 C36 1.371(4) . ?
C35 C38 1.513(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.388(4) . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
O3 S1 1.436(2) . ?
O4 S1 1.437(2) . ?
O5 S2 1.433(2) . ?
O6 S2 1.433(2) . ?
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
C1 C2 C3 C4 1.6(6) . . . . ?
C1 C6 C7 C8 118.5(3) . . . . ?
C1 C6 C7 C12 -63.2(4) . . . . ?
C2 C1 C6 C5 -2.6(5) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C2 C3 C4 C5 -1.6(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 2.6(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 -58.4(4) . . . . ?
C5 C6 C7 C12 119.9(4) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C6 C7 C8 N1 -179.7(3) . . . . ?
C6 C7 C12 C11 178.7(3) . . . . ?
C6 C7 C12 F2 -1.1(5) . . . . ?
C7 C8 N1 C10 -0.1(4) . . . . ?
C8 C7 C12 C11 -3.0(5) . . . . ?
C8 C7 C12 F2 177.2(3) . . . . ?
C10 C11 C12 C7 2.3(5) . . . . ?
C10 C11 C12 F2 -177.9(3) . . . . ?
C11 C10 N1 C8 -0.7(4) . . . . ?
C11 C10 S2 C13 120.1(2) . . . . ?
C11 C10 S2 O5 -124.4(2) . . . . ?
C11 C10 S2 O6 5.1(3) . . . . ?
C12 C7 C8 N1 1.9(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C14 C13 S2 C10 90.7(2) . . . . ?
C14 C13 S2 O5 -23.5(3) . . . . ?
C14 C13 S2 O6 -156.2(2) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C14 C15 C16 C19 179.1(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C18 C13 C14 C15 -0.7(4) . . . . ?
C18 C13 S2 C10 -87.6(2) . . . . ?
C18 C13 S2 O5 158.2(2) . . . . ?
C18 C13 S2 O6 25.5(2) . . . . ?
C19 C16 C17 C18 -179.3(3) . . . . ?
C20 C21 C22 C23 0.8(6) . . . . ?
C20 C25 C26 C27 101.7(4) . . . . ?
C20 C25 C26 C31 -80.2(4) . . . . ?
C21 C20 C25 C24 0.6(5) . . . . ?
C21 C20 C25 C26 -176.8(3) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
C22 C23 C24 C25 0.2(6) . . . . ?
C23 C24 C25 C20 -0.2(5) . . . . ?
C23 C24 C25 C26 177.1(3) . . . . ?
C24 C25 C26 C27 -75.5(4) . . . . ?
C24 C25 C26 C31 102.5(3) . . . . ?
C25 C20 C21 C22 -0.8(6) . . . . ?
C25 C26 C27 N2 178.0(3) . . . . ?
C25 C26 C31 C30 -177.0(2) . . . . ?
C25 C26 C31 F1 2.2(4) . . . . ?
C26 C27 N2 C29 -0.4(5) . . . . ?
C27 C26 C31 C30 1.1(4) . . . . ?
C27 C26 C31 F1 -179.7(2) . . . . ?
C29 C30 C31 C26 -1.3(4) . . . . ?
C29 C30 C31 F1 179.5(2) . . . . ?
C30 C29 N2 C27 0.1(4) . . . . ?
C30 C29 S1 C32 -103.4(2) . . . . ?
C30 C29 S1 O3 141.7(2) . . . . ?
C30 C29 S1 O4 11.9(3) . . . . ?
C31 C26 C27 N2 -0.2(4) . . . . ?
C32 C33 C34 C35 1.1(4) . . . . ?
C33 C32 C37 C36 0.6(4) . . . . ?
C33 C32 S1 C29 84.8(2) . . . . ?
C33 C32 S1 O3 -161.4(2) . . . . ?
C33 C32 S1 O4 -28.8(2) . . . . ?
C33 C34 C35 C36 -0.7(4) . . . . ?
C33 C34 C35 C38 -179.7(3) . . . . ?
C34 C35 C36 C37 0.3(4) . . . . ?
C35 C36 C37 C32 -0.2(4) . . . . ?
C37 C32 C33 C34 -1.0(4) . . . . ?
C37 C32 S1 C29 -93.6(2) . . . . ?
C37 C32 S1 O3 20.3(2) . . . . ?
C37 C32 S1 O4 152.9(2) . . . . ?
C38 C35 C36 C37 179.3(3) . . . . ?
Cl1 C1 C2 C3 -178.4(3) . . . . ?
Cl1 C1 C6 C5 176.3(2) . . . . ?
Cl1 C1 C6 C7 -0.6(4) . . . . ?
Cl2 C20 C21 C22 -179.7(3) . . . . ?
Cl2 C20 C25 C24 179.4(2) . . . . ?
Cl2 C20 C25 C26 2.1(4) . . . . ?
N1 C10 C11 C12 -0.3(4) . . . . ?
N1 C10 S2 C13 -59.1(2) . . . . ?
N1 C10 S2 O5 56.3(2) . . . . ?
N1 C10 S2 O6 -174.1(2) . . . . ?
N2 C29 C30 C31 0.7(4) . . . . ?
N2 C29 S1 C32 74.6(2) . . . . ?
N2 C29 S1 O3 -40.3(2) . . . . ?
N2 C29 S1 O4 -170.1(2) . . . . ?
S1 C29 C30 C31 178.53(19) . . . . ?
S1 C29 N2 C27 -177.8(2) . . . . ?
S1 C32 C33 C34 -179.3(2) . . . . ?
S1 C32 C37 C36 178.9(2) . . . . ?
S2 C10 C11 C12 -179.5(2) . . . . ?
S2 C10 N1 C8 178.5(2) . . . . ?
S2 C13 C14 C15 -178.9(2) . . . . ?
S2 C13 C18 C17 178.8(2) . . . . ?
