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#$Date: 2023-04-04 13:11:20 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282323 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246374.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_7246374
loop_
_publ_author_name
'Kolesnik, Irina A.'
'Potkin, Vladimir I.'
'Grigoriev, Mikhail S.'
'Novikov, Anton P.'
'Gomila, Rosa M.'
'Podrezova, Alexandra G.'
'Brazhkin, Vadim V.'
'Zubkov, Fedor I.'
'Frontera, Antonio'
_publ_section_title
;
 Synthesis, X-ray characterization and DFT calculations of a series of
 3-substituted 4,5-dichloroisothiazoles
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1976
_journal_page_last               1985
_journal_paper_doi               10.1039/D3CE00112A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C14 H14 Cl2 N2 O2 S'
_chemical_formula_weight         345.23
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-18 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.990(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2276(5)
_cell_length_b                   26.5464(19)
_cell_length_c                   8.5613(6)
_cell_measurement_reflns_used    3912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      3.14
_cell_volume                     1512.16(19)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25913
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.337
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9229
_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            yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       fragment
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 2247 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         8579
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0507
_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)+(0.0353P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                6270
_reflns_number_total             8579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00112a2.cif
_cod_data_source_block           I681
_cod_depositor_comments
'Adding full bibliography for 7246372--7246377.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7246374
_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.
;
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.914
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
Cl1 Cl 0.70922(16) 0.59150(4) 0.45439(14) 0.0150(2) Uani 1 1 d . . . . .
Cl2 Cl 0.67179(19) 0.48511(5) 0.64165(15) 0.0241(3) Uani 1 1 d . . . . .
S1 S 0.2376(2) 0.51665(5) 0.52255(16) 0.0198(3) Uani 1 1 d . . . . .
O1 O 0.4278(5) 0.63844(15) 0.0658(4) 0.0258(9) Uani 1 1 d . . . . .
O2 O 0.4720(5) 0.69944(14) 0.5707(5) 0.0274(9) Uani 1 1 d . . . . .
N1 N -0.1553(5) 0.65402(16) 0.1639(5) 0.0142(9) Uani 1 1 d D . . . .
H1 H -0.274(5) 0.654(2) 0.139(6) 0.017 Uiso 1 1 d D U . . .
N2 N 0.1528(6) 0.56982(16) 0.4179(5) 0.0172(9) Uani 1 1 d . . . . .
C2 C -0.0731(7) 0.63421(19) 0.0577(6) 0.0130(11) Uani 1 1 d . . . . .
C3 C 0.1319(7) 0.63451(17) 0.1117(5) 0.0099(9) Uani 1 1 d . . . . .
C4 C 0.2553(7) 0.64386(17) 0.2985(5) 0.0114(9) Uani 1 1 d . . . . .
H4A H 0.386165 0.659184 0.309261 0.014 Uiso 1 1 calc R U . . .
C5 C 0.1516(7) 0.68029(17) 0.3755(6) 0.0111(9) Uani 1 1 d . . . . .
C6 C -0.0512(7) 0.68224(19) 0.3086(6) 0.0128(10) Uani 1 1 d . . . . .
C7 C -0.2273(7) 0.6155(2) -0.1066(6) 0.0169(10) Uani 1 1 d . . . . .
H7A H -0.346089 0.603823 -0.088568 0.025 Uiso 1 1 calc R U . . .
H7B H -0.171098 0.587565 -0.148788 0.025 Uiso 1 1 calc R U . . .
H7C H -0.265716 0.642895 -0.189980 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2455(7) 0.63017(18) 0.0038(6) 0.0122(10) Uani 1 1 d . . . . .
C9 C 0.1496(7) 0.6179(2) -0.1824(6) 0.0180(11) Uani 1 1 d . . . . .
H9A H 0.033339 0.639896 -0.237422 0.027 Uiso 1 1 calc R U . . .
H9B H 0.105640 0.582651 -0.196925 0.027 Uiso 1 1 calc R U . . .
H9C H 0.247479 0.623105 -0.234155 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2910(8) 0.70719(19) 0.5254(6) 0.0137(10) Uani 1 1 d . . . . .
C11 C 0.2232(7) 0.74221(19) 0.6295(6) 0.0194(11) Uani 1 1 d . . . . .
H11A H 0.136531 0.723961 0.674227 0.029 Uiso 1 1 calc R U . . .
H11B H 0.147985 0.770238 0.558539 0.029 Uiso 1 1 calc R U . . .
H11C H 0.340612 0.755364 0.724050 0.029 Uiso 1 1 calc R U . . .
C12 C -0.1887(7) 0.71349(19) 0.3643(6) 0.0175(11) Uani 1 1 d . . . . .
H12A H -0.328779 0.706856 0.289255 0.026 Uiso 1 1 calc R U . . .
H12B H -0.158847 0.749295 0.358844 0.026 Uiso 1 1 calc R U . . .
H12C H -0.167979 0.704612 0.481113 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3001(7) 0.59416(19) 0.3948(5) 0.0118(9) Uani 1 1 d . . . . .
C14 C 0.4903(7) 0.56963(18) 0.4645(6) 0.0115(9) Uani 1 1 d . . . . .
C15 C 0.4786(7) 0.52539(18) 0.5393(6) 0.0158(11) Uani 1 1 d . . . . .
Cl21 Cl 0.60100(16) 0.40731(5) 0.93553(14) 0.0177(3) Uani 1 1 d . . . . .
Cl22 Cl 0.5683(2) 0.51400(5) 1.12360(16) 0.0291(3) Uani 1 1 d . . . . .
S21 S 0.1363(2) 0.48261(5) 1.01216(16) 0.0220(3) Uani 1 1 d . . . . .
O21 O 0.3170(5) 0.37323(16) 0.5532(4) 0.0266(10) Uani 1 1 d . . . . .
O22 O 0.3589(5) 0.30230(16) 1.0534(4) 0.0249(9) Uani 1 1 d . . . . .
N21 N -0.2702(6) 0.34561(16) 0.6426(5) 0.0143(9) Uani 1 1 d D . . . .
H21 H -0.387(5) 0.350(2) 0.614(6) 0.017 Uiso 1 1 d D U . . .
N22 N 0.0479(6) 0.43000(15) 0.9046(5) 0.0166(9) Uani 1 1 d . . . . .
C22 C -0.1874(7) 0.36581(19) 0.5379(5) 0.0120(10) Uani 1 1 d . . . . .
C23 C 0.0176(7) 0.36632(18) 0.5923(6) 0.0115(10) Uani 1 1 d . . . . .
C24 C 0.1416(6) 0.35643(17) 0.7784(5) 0.0106(9) Uani 1 1 d . . . . .
H24A H 0.271117 0.340752 0.787200 0.013 Uiso 1 1 calc R U . . .
C25 C 0.0396(7) 0.32008(18) 0.8556(6) 0.0117(10) Uani 1 1 d . . . . .
C26 C -0.1660(7) 0.31766(17) 0.7865(5) 0.0108(9) Uani 1 1 d . . . . .
C27 C -0.3425(7) 0.38318(19) 0.3706(6) 0.0159(10) Uani 1 1 d . . . . .
H27A H -0.291975 0.412784 0.331290 0.024 Uiso 1 1 calc R U . . .
H27B H -0.466755 0.391990 0.384718 0.024 Uiso 1 1 calc R U . . .
H27C H -0.369806 0.356066 0.286853 0.024 Uiso 1 1 calc R U . . .
C28 C 0.1318(7) 0.37472(18) 0.4861(6) 0.0133(10) Uani 1 1 d . . . . .
C29 C 0.0367(7) 0.3840(2) 0.2987(6) 0.0209(11) Uani 1 1 d . . . . .
H29A H -0.073757 0.360152 0.246391 0.031 Uiso 1 1 calc R U . . .
H29B H 0.137268 0.379533 0.249383 0.031 Uiso 1 1 calc R U . . .
H29C H -0.015686 0.418522 0.277662 0.031 Uiso 1 1 calc R U . . .
C30 C 0.1787(7) 0.29376(18) 1.0073(6) 0.0152(10) Uani 1 1 d . . . . .
C31 C 0.1097(7) 0.25788(19) 1.1094(6) 0.0200(11) Uani 1 1 d . . . . .
H31A H 0.024485 0.231826 1.034542 0.030 Uiso 1 1 calc R U . . .
H31B H 0.032866 0.276361 1.163123 0.030 Uiso 1 1 calc R U . . .
H31C H 0.226898 0.242072 1.197129 0.030 Uiso 1 1 calc R U . . .
C32 C -0.3012(7) 0.28672(19) 0.8445(6) 0.0183(11) Uani 1 1 d . . . . .
H32A H -0.441813 0.294340 0.773635 0.027 Uiso 1 1 calc R U . . .
H32B H -0.274537 0.294770 0.963101 0.027 Uiso 1 1 calc R U . . .
H32C H -0.275445 0.250850 0.834757 0.027 Uiso 1 1 calc R U . . .
C33 C 0.1917(6) 0.40562(19) 0.8773(5) 0.0109(9) Uani 1 1 d . . . . .
C34 C 0.3834(7) 0.42926(18) 0.9446(6) 0.0131(10) Uani 1 1 d . . . . .
C35 C 0.3770(8) 0.4733(2) 1.0253(6) 0.0176(12) 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'
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'
Cl Cl 0.1484 0.1585 '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
N2 S1 C15 94.5(2) . . ?
C2 N1 C6 125.0(4) . . ?
C2 N1 H1 121(4) . . ?
C6 N1 H1 113(4) . . ?
C13 N2 S1 110.3(3) . . ?
C3 C2 N1 117.8(4) . . ?
C3 C2 C7 129.0(4) . . ?
N1 C2 C7 113.2(4) . . ?
C2 C3 C8 126.0(4) . . ?
C2 C3 C4 118.1(4) . . ?
C8 C3 C4 115.8(4) . . ?
C3 C4 C13 110.0(4) . . ?
C3 C4 C5 112.0(4) . . ?
C13 C4 C5 110.6(3) . . ?
C3 C4 H4A 108.0 . . ?
C13 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
C6 C5 C10 127.7(4) . . ?
C6 C5 C4 118.5(4) . . ?
C10 C5 C4 113.6(4) . . ?
C5 C6 N1 118.5(4) . . ?
C5 C6 C12 128.8(4) . . ?
N1 C6 C12 112.6(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C3 118.9(4) . . ?
O1 C8 C9 117.8(4) . . ?
C3 C8 C9 123.2(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C5 118.5(4) . . ?
O2 C10 C11 118.2(4) . . ?
C5 C10 C11 123.3(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 114.5(5) . . ?
N2 C13 C4 119.4(4) . . ?
C14 C13 C4 126.1(4) . . ?
C15 C14 C13 111.5(4) . . ?
C15 C14 Cl1 123.0(4) . . ?
C13 C14 Cl1 125.5(4) . . ?
C14 C15 Cl2 126.6(4) . . ?
C14 C15 S1 109.1(3) . . ?
Cl2 C15 S1 124.2(3) . . ?
N22 S21 C35 94.3(2) . . ?
C22 N21 C26 124.7(4) . . ?
C22 N21 H21 115(4) . . ?
C26 N21 H21 120(4) . . ?
C33 N22 S21 110.6(4) . . ?
N21 C22 C23 118.3(4) . . ?
N21 C22 C27 113.0(4) . . ?
C23 C22 C27 128.7(4) . . ?
C22 C23 C28 126.0(4) . . ?
C22 C23 C24 118.2(4) . . ?
C28 C23 C24 115.7(4) . . ?
C25 C24 C23 112.4(4) . . ?
C25 C24 C33 110.8(3) . . ?
C23 C24 C33 110.5(4) . . ?
C25 C24 H24A 107.6 . . ?
C23 C24 H24A 107.6 . . ?
C33 C24 H24A 107.6 . . ?
C26 C25 C30 127.7(4) . . ?
C26 C25 C24 118.2(4) . . ?
C30 C25 C24 114.0(4) . . ?
C25 C26 N21 118.8(4) . . ?
C25 C26 C32 128.2(4) . . ?
N21 C26 C32 113.0(4) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O21 C28 C23 118.5(4) . . ?
O21 C28 C29 117.7(4) . . ?
C23 C28 C29 123.7(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O22 C30 C25 118.1(4) . . ?
O22 C30 C31 118.8(4) . . ?
C25 C30 C31 123.1(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C26 C32 H32A 109.5 . . ?
C26 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C26 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N22 C33 C34 114.9(5) . . ?
N22 C33 C24 119.1(4) . . ?
C34 C33 C24 125.9(4) . . ?
C35 C34 C33 111.2(4) . . ?
C35 C34 Cl21 121.9(4) . . ?
C33 C34 Cl21 126.9(4) . . ?
C34 C35 Cl22 127.8(4) . . ?
C34 C35 S21 108.9(4) . . ?
Cl22 C35 S21 123.3(3) . . ?
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
Cl1 C14 1.719(5) . ?
Cl2 C15 1.705(5) . ?
S1 N2 1.656(4) . ?
S1 C15 1.707(5) . ?
O1 C8 1.233(5) . ?
O2 C10 1.228(6) . ?
N1 C2 1.370(6) . ?
N1 C6 1.391(6) . ?
N1 H1 0.80(3) . ?
N2 C13 1.325(6) . ?
C2 C3 1.369(6) . ?
C2 C7 1.498(6) . ?
C3 C8 1.460(6) . ?
C3 C4 1.517(6) . ?
C4 C13 1.522(6) . ?
C4 C5 1.523(6) . ?
C4 H4A 1.0000 . ?
C5 C6 1.350(6) . ?
C5 C10 1.470(6) . ?
C6 C12 1.508(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.505(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.497(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.424(6) . ?
C14 C15 1.356(6) . ?
Cl21 C34 1.707(5) . ?
Cl22 C35 1.697(5) . ?
S21 N22 1.657(4) . ?
S21 C35 1.717(5) . ?
O21 C28 1.234(5) . ?
O22 C30 1.225(5) . ?
N21 C22 1.366(6) . ?
N21 C26 1.382(6) . ?
N21 H21 0.79(3) . ?
N22 C33 1.320(5) . ?
C22 C23 1.369(6) . ?
C22 C27 1.505(6) . ?
C23 C28 1.464(6) . ?
C23 C24 1.515(6) . ?
C24 C25 1.514(6) . ?
C24 C33 1.521(6) . ?
C24 H24A 1.0000 . ?
C25 C26 1.370(6) . ?
C25 C30 1.471(7) . ?
C26 C32 1.502(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.499(6) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.504(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.422(6) . ?
C34 C35 1.368(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.80(3) 2.04(4) 2.825(5) 169(5) 1_455 yes
C4 H4A Cl1 1.00 2.82 3.325(4) 111.8 . yes
C11 H11C O22 0.98 2.58 3.554(6) 171.4 2_657 yes
N21 H21 O21 0.79(3) 2.09(4) 2.871(5) 170(5) 1_455 yes
C27 H27B O21 0.98 2.56 3.403(5) 144.6 1_455 yes
C31 H31C O2 0.98 2.57 3.546(6) 178.6 2_647 yes
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
C15 S1 N2 C13 0.0(3) . . . . ?
C6 N1 C2 C3 11.8(7) . . . . ?
C6 N1 C2 C7 -167.4(4) . . . . ?
N1 C2 C3 C8 -159.9(5) . . . . ?
C7 C2 C3 C8 19.1(8) . . . . ?
N1 C2 C3 C4 15.4(6) . . . . ?
C7 C2 C3 C4 -165.5(5) . . . . ?
C2 C3 C4 C13 89.3(5) . . . . ?
C8 C3 C4 C13 -94.9(5) . . . . ?
C2 C3 C4 C5 -34.2(5) . . . . ?
C8 C3 C4 C5 141.6(4) . . . . ?
C3 C4 C5 C6 28.9(6) . . . . ?
C13 C4 C5 C6 -94.3(5) . . . . ?
C3 C4 C5 C10 -155.0(4) . . . . ?
C13 C4 C5 C10 81.9(5) . . . . ?
C10 C5 C6 N1 179.3(4) . . . . ?
C4 C5 C6 N1 -5.3(6) . . . . ?
C10 C5 C6 C12 2.4(8) . . . . ?
C4 C5 C6 C12 177.9(4) . . . . ?
C2 N1 C6 C5 -17.3(7) . . . . ?
C2 N1 C6 C12 160.0(4) . . . . ?
C2 C3 C8 O1 169.4(5) . . . . ?
C4 C3 C8 O1 -6.1(7) . . . . ?
C2 C3 C8 C9 -8.3(7) . . . . ?
C4 C3 C8 C9 176.3(4) . . . . ?
C6 C5 C10 O2 177.8(5) . . . . ?
C4 C5 C10 O2 2.1(6) . . . . ?
C6 C5 C10 C11 0.0(7) . . . . ?
C4 C5 C10 C11 -175.6(4) . . . . ?
S1 N2 C13 C14 -0.4(5) . . . . ?
S1 N2 C13 C4 179.0(3) . . . . ?
C3 C4 C13 N2 -71.0(5) . . . . ?
C5 C4 C13 N2 53.2(5) . . . . ?
C3 C4 C13 C14 108.4(5) . . . . ?
C5 C4 C13 C14 -127.4(5) . . . . ?
N2 C13 C14 C15 0.8(6) . . . . ?
C4 C13 C14 C15 -178.6(4) . . . . ?
N2 C13 C14 Cl1 179.7(3) . . . . ?
C4 C13 C14 Cl1 0.2(7) . . . . ?
C13 C14 C15 Cl2 -178.5(4) . . . . ?
Cl1 C14 C15 Cl2 2.6(6) . . . . ?
C13 C14 C15 S1 -0.7(5) . . . . ?
Cl1 C14 C15 S1 -179.6(3) . . . . ?
N2 S1 C15 C14 0.4(3) . . . . ?
N2 S1 C15 Cl2 178.2(3) . . . . ?
C35 S21 N22 C33 -0.2(3) . . . . ?
C26 N21 C22 C23 -11.9(7) . . . . ?
C26 N21 C22 C27 165.9(4) . . . . ?
N21 C22 C23 C28 164.3(5) . . . . ?
C27 C22 C23 C28 -13.2(8) . . . . ?
N21 C22 C23 C24 -14.5(6) . . . . ?
C27 C22 C23 C24 168.0(5) . . . . ?
C22 C23 C24 C25 32.8(6) . . . . ?
C28 C23 C24 C25 -146.1(4) . . . . ?
C22 C23 C24 C33 -91.6(5) . . . . ?
C28 C23 C24 C33 89.5(5) . . . . ?
C23 C24 C25 C26 -27.5(6) . . . . ?
C33 C24 C25 C26 96.7(5) . . . . ?
C23 C24 C25 C30 156.6(4) . . . . ?
C33 C24 C25 C30 -79.2(5) . . . . ?
C30 C25 C26 N21 179.9(4) . . . . ?
C24 C25 C26 N21 4.6(6) . . . . ?
C30 C25 C26 C32 -1.7(8) . . . . ?
C24 C25 C26 C32 -177.0(4) . . . . ?
C22 N21 C26 C25 17.2(7) . . . . ?
C22 N21 C26 C32 -161.4(4) . . . . ?
C22 C23 C28 O21 -178.8(5) . . . . ?
C24 C23 C28 O21 0.0(7) . . . . ?
C22 C23 C28 C29 -0.1(8) . . . . ?
C24 C23 C28 C29 178.7(4) . . . . ?
C26 C25 C30 O22 -177.2(5) . . . . ?
C24 C25 C30 O22 -1.8(6) . . . . ?
C26 C25 C30 C31 1.5(8) . . . . ?
C24 C25 C30 C31 176.9(4) . . . . ?
S21 N22 C33 C34 0.1(5) . . . . ?
S21 N22 C33 C24 -179.3(3) . . . . ?
C25 C24 C33 N22 -53.3(5) . . . . ?
C23 C24 C33 N22 72.0(5) . . . . ?
C25 C24 C33 C34 127.4(4) . . . . ?
C23 C24 C33 C34 -107.3(5) . . . . ?
N22 C33 C34 C35 0.1(6) . . . . ?
C24 C33 C34 C35 179.5(4) . . . . ?
N22 C33 C34 Cl21 178.6(3) . . . . ?
C24 C33 C34 Cl21 -2.0(7) . . . . ?
C33 C34 C35 Cl22 -179.8(4) . . . . ?
Cl21 C34 C35 Cl22 1.6(6) . . . . ?
C33 C34 C35 S21 -0.2(5) . . . . ?
Cl21 C34 C35 S21 -178.8(3) . . . . ?
N22 S21 C35 C34 0.3(4) . . . . ?
N22 S21 C35 Cl22 179.9(3) . . . . ?
