#------------------------------------------------------------------------------
#$Date: 2020-08-07 02:26:19 +0300 (Fri, 07 Aug 2020) $
#$Revision: 255141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038653.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_4038653
loop_
_publ_author_name
'Dressler, Justin'
'Barker, Joshua E.'
'Karas, Lucas J.'
'Hashimoto, Hannah'
'Kishi, Ryohei'
'Zakharov, Lev N.'
'MacMillan, Samantha N.'
'Gómez-García, Carlos J'
'Nakano, Masayoshi'
'Wu, Judy I.'
'Haley, Michael M.'
_publ_section_title
;
 Late-stage Modification of Electronic Properties of Antiaromatic and
 Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01387
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C54 H48 Cl6 N2 O4 S2'
_chemical_formula_weight         1065.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.21(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.949(3)
_cell_length_b                   25.877(6)
_cell_length_c                   16.528(5)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.75
_cell_measurement_theta_min      4.11
_cell_volume                     5058(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.1666
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17136
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.934
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'incoatec i\mS'
_exptl_absorpt_coefficient_mu    4.257
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       cut-strip
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_platon_squeeze_details
;
Solvent molecule CHCl3, 58 electrons, is highly disordered
and was treated by SQUEEZE
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.28(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         6906
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0719
_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)+(0.0155P)²+2.4670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.2030
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4610
_reflns_number_total             6906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01387_si_005.cif
_cod_data_source_block           cu_mh263_0m_a_sqd
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4038653
_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_min   0.587
_shelx_estimated_absorpt_t_max   0.920
_platon_squeeze_void_probe_radius 1.20
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
S1 S 0.7793(2) 0.20937(9) 0.86568(15) 0.0634(7) Uani 1 1 d . . . . .
S2 S 0.3960(2) 0.55047(8) 0.34089(16) 0.0623(7) Uani 1 1 d . . . . .
O1 O 0.8985(6) 0.2069(3) 0.8637(5) 0.085(3) Uani 1 1 d . . . . .
O2 O 0.7401(7) 0.2129(3) 0.9421(5) 0.078(2) Uani 1 1 d . . . . .
O3 O 0.2776(6) 0.5552(3) 0.3421(6) 0.082(3) Uani 1 1 d . . . . .
O4 O 0.4355(9) 0.5472(3) 0.2642(5) 0.091(3) Uani 1 1 d . . . . .
N1 N 0.7342(7) 0.2602(3) 0.8124(5) 0.059(2) Uani 1 1 d . . . . .
N2 N 0.4383(6) 0.4973(3) 0.3908(5) 0.056(2) Uani 1 1 d . . . . .
C1 C 0.6471(7) 0.3513(3) 0.7033(6) 0.049(2) Uani 1 1 d . . . . .
H1B H 0.6782 0.3639 0.7557 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6406(7) 0.3000(3) 0.6874(6) 0.048(2) Uani 1 1 d . . . . .
C3 C 0.5889(7) 0.2796(3) 0.6119(5) 0.047(2) Uani 1 1 d . . . . .
C4 C 0.5463(7) 0.3117(3) 0.5489(5) 0.047(2) Uani 1 1 d . . . . .
H4B H 0.5118 0.2982 0.4980 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5557(7) 0.3665(3) 0.5627(5) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.6055(7) 0.3857(3) 0.6383(5) 0.0427(19) Uani 1 1 d . . . . .
C7 C 0.6174(8) 0.4395(3) 0.6511(6) 0.055(2) Uani 1 1 d . . . . .
H7A H 0.6512 0.4527 0.7024 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5795(7) 0.4720(3) 0.5887(6) 0.048(2) Uani 1 1 d . . . . .
C9 C 0.5264(7) 0.4534(3) 0.5151(5) 0.047(2) Uani 1 1 d . . . . .
C10 C 0.5123(7) 0.4017(3) 0.4990(5) 0.050(2) Uani 1 1 d . . . . .
H10A H 0.4753 0.3897 0.4478 0.060 Uiso 1 1 calc R U . . .
C11 C 0.6799(7) 0.2553(3) 0.7421(6) 0.048(2) Uani 1 1 d . . . . .
C12 C 0.6452(7) 0.2079(3) 0.6935(6) 0.045(2) Uani 1 1 d . . . . .
C13 C 0.5934(7) 0.2224(3) 0.6192(6) 0.048(2) Uani 1 1 d . . . . .
C14 C 0.6642(7) 0.1576(3) 0.7335(6) 0.048(2) Uani 1 1 d . . . . .
C15 C 0.7163(7) 0.1544(3) 0.8118(6) 0.054(2) Uani 1 1 d . . . . .
C16 C 0.7301(8) 0.1089(4) 0.8574(6) 0.059(3) Uani 1 1 d . . . . .
H16A H 0.7654 0.1088 0.9126 0.071 Uiso 1 1 calc R U . . .
C17 C 0.6912(9) 0.0653(3) 0.8196(8) 0.066(3) Uani 1 1 d . . . . .
H17A H 0.7001 0.0335 0.8485 0.080 Uiso 1 1 calc R U . . .
C18 C 0.6385(8) 0.0654(4) 0.7399(7) 0.067(3) Uani 1 1 d . . . . .
H18A H 0.6120 0.0339 0.7149 0.080 Uiso 1 1 calc R U . . .
C19 C 0.6236(8) 0.1117(3) 0.6950(7) 0.060(3) Uani 1 1 d . . . . .
H19A H 0.5870 0.1118 0.6401 0.072 Uiso 1 1 calc R U . . .
C20 C 0.5835(7) 0.5300(3) 0.5851(6) 0.053(2) Uani 1 1 d . . . . .
C21 C 0.5324(7) 0.5460(3) 0.5108(6) 0.047(2) Uani 1 1 d . . . . .
C22 C 0.4925(7) 0.4995(3) 0.4621(6) 0.051(2) Uani 1 1 d . . . . .
C23 C 0.5189(7) 0.5981(3) 0.4735(6) 0.049(2) Uani 1 1 d . . . . .
C24 C 0.4641(7) 0.6033(3) 0.3951(6) 0.052(2) Uani 1 1 d . . . . .
C25 C 0.4534(8) 0.6504(4) 0.3551(6) 0.062(3) Uani 1 1 d . . . . .
H25A H 0.4161 0.6524 0.3004 0.075 Uiso 1 1 calc R U . . .
C26 C 0.4965(8) 0.6939(4) 0.3943(7) 0.065(3) Uani 1 1 d . . . . .
H26A H 0.4900 0.7264 0.3672 0.078 Uiso 1 1 calc R U . . .
C27 C 0.5507(9) 0.6903(4) 0.4753(7) 0.067(3) Uani 1 1 d . . . . .
H27A H 0.5799 0.7206 0.5031 0.080 Uiso 1 1 calc R U . . .
C28 C 0.5623(7) 0.6428(3) 0.5153(6) 0.051(2) Uani 1 1 d . . . . .
H28A H 0.5991 0.6406 0.5701 0.062 Uiso 1 1 calc R U . . .
C30 C 0.5435(7) 0.1873(3) 0.5503(6) 0.047(2) Uani 1 1 d . . . . .
C31 C 0.4285(8) 0.1772(3) 0.5418(6) 0.050(2) Uani 1 1 d . . . . .
C32 C 0.3855(8) 0.1406(4) 0.4846(6) 0.059(2) Uani 1 1 d . . . . .
H32A H 0.3065 0.1339 0.4777 0.071 Uiso 1 1 calc R U . . .
C33 C 0.4520(8) 0.1132(3) 0.4367(6) 0.055(2) Uani 1 1 d . . . . .
C34 C 0.5676(8) 0.1264(4) 0.4461(6) 0.061(3) Uani 1 1 d . . . . .
H34A H 0.6152 0.1095 0.4130 0.073 Uiso 1 1 calc R U . . .
C35 C 0.6140(8) 0.1629(3) 0.5014(6) 0.054(2) Uani 1 1 d . . . . .
C36 C 0.3528(9) 0.2032(4) 0.5936(7) 0.067(3) Uani 1 1 d . . . . .
H36A H 0.2751 0.1908 0.5781 0.100 Uiso 1 1 calc R U . . .
H36B H 0.3781 0.1950 0.6512 0.100 Uiso 1 1 calc R U . . .
H36C H 0.3554 0.2406 0.5855 0.100 Uiso 1 1 calc R U . . .
C37 C 0.7394(8) 0.1735(4) 0.5123(7) 0.068(3) Uani 1 1 d . . . . .
H37A H 0.7579 0.2004 0.5538 0.102 Uiso 1 1 calc R U . . .
H37B H 0.7808 0.1418 0.5298 0.102 Uiso 1 1 calc R U . . .
H37C H 0.7609 0.1852 0.4603 0.102 Uiso 1 1 calc R U . . .
C38 C 0.4097(10) 0.0697(5) 0.3790(8) 0.083(4) Uani 1 1 d . . . . .
C39 C 0.4212(13) 0.0866(8) 0.2917(9) 0.123(6) Uani 1 1 d . . . . .
H39A H 0.3773 0.1183 0.2784 0.184 Uiso 1 1 calc R U . . .
H39B H 0.5010 0.0932 0.2877 0.184 Uiso 1 1 calc R U . . .
H39C H 0.3927 0.0592 0.2533 0.184 Uiso 1 1 calc R U . . .
C40 C 0.2859(9) 0.0570(4) 0.3810(7) 0.071(3) Uani 1 1 d . . . . .
H40A H 0.2400 0.0880 0.3671 0.106 Uiso 1 1 calc R U . . .
H40B H 0.2620 0.0296 0.3413 0.106 Uiso 1 1 calc R U . . .
H40C H 0.2761 0.0453 0.4359 0.106 Uiso 1 1 calc R U . . .
C41 C 0.4763(12) 0.0213(4) 0.4006(11) 0.130(7) Uani 1 1 d . . . . .
H41A H 0.5568 0.0282 0.3998 0.195 Uiso 1 1 calc R U . . .
H41B H 0.4649 0.0099 0.4553 0.195 Uiso 1 1 calc R U . . .
H41C H 0.4508 -0.0058 0.3607 0.195 Uiso 1 1 calc R U . . .
C42 C 0.6404(8) 0.5592(3) 0.6584(6) 0.050(2) Uani 1 1 d . . . . .
C43 C 0.7595(7) 0.5597(3) 0.6729(6) 0.047(2) Uani 1 1 d . . . . .
C44 C 0.8102(7) 0.5865(3) 0.7415(5) 0.048(2) Uani 1 1 d . . . . .
H44A H 0.8903 0.5885 0.7512 0.058 Uiso 1 1 calc R U . . .
C45 C 0.7485(8) 0.6106(3) 0.7970(6) 0.053(2) Uani 1 1 d . . . . .
C46 C 0.6334(8) 0.6085(4) 0.7815(7) 0.063(3) Uani 1 1 d . . . . .
H46A H 0.5900 0.6242 0.8187 0.076 Uiso 1 1 calc R U . . .
C47 C 0.5775(7) 0.5835(3) 0.7118(6) 0.050(2) Uani 1 1 d . . . . .
C48 C 0.8295(7) 0.5335(4) 0.6183(6) 0.058(2) Uani 1 1 d . . . . .
H48A H 0.7802 0.5167 0.5734 0.087 Uiso 1 1 calc R U . . .
H48B H 0.8774 0.5590 0.5959 0.087 Uiso 1 1 calc R U . . .
H48C H 0.8772 0.5075 0.6494 0.087 Uiso 1 1 calc R U . . .
C49 C 0.4490(8) 0.5846(4) 0.6976(8) 0.073(3) Uani 1 1 d . . . . .
H49A H 0.4215 0.6036 0.7421 0.109 Uiso 1 1 calc R U . . .
H49B H 0.4229 0.6019 0.6455 0.109 Uiso 1 1 calc R U . . .
H49C H 0.4199 0.5492 0.6959 0.109 Uiso 1 1 calc R U . . .
C50 C 0.8121(9) 0.6381(4) 0.8752(8) 0.072(3) Uani 1 1 d . . . . .
C51 C 0.8000(11) 0.6025(5) 0.9490(8) 0.083(3) Uani 1 1 d . . . . .
H51A H 0.7197 0.5958 0.9510 0.125 Uiso 1 1 calc R U . . .
H51B H 0.8391 0.5698 0.9430 0.125 Uiso 1 1 calc R U . . .
H51C H 0.8335 0.6196 0.9997 0.125 Uiso 1 1 calc R U . . .
C52 C 0.9336(8) 0.6480(5) 0.8726(7) 0.078(3) Uani 1 1 d . . . . .
H52A H 0.9718 0.6153 0.8641 0.117 Uiso 1 1 calc R U . . .
H52B H 0.9416 0.6717 0.8275 0.117 Uiso 1 1 calc R U . . .
H52C H 0.9677 0.6635 0.9244 0.117 Uiso 1 1 calc R U . . .
C53 C 0.7523(12) 0.6892(4) 0.8884(9) 0.094(4) Uani 1 1 d . . . . .
H53A H 0.6719 0.6827 0.8901 0.142 Uiso 1 1 calc R U . . .
H53B H 0.7865 0.7047 0.9402 0.142 Uiso 1 1 calc R U . . .
H53C H 0.7603 0.7129 0.8433 0.142 Uiso 1 1 calc R U . . .
C1S C 0.2143(11) 0.5609(5) 0.1150(9) 0.088(4) Uani 1 1 d . . . . .
H1SA H 0.2458 0.5512 0.1723 0.105 Uiso 1 1 calc R U . . .
Cl1S Cl 0.2728(4) 0.61953(16) 0.0940(3) 0.1295(16) Uani 1 1 d . . . . .
Cl2S Cl 0.0676(3) 0.56596(17) 0.1100(3) 0.1186(14) Uani 1 1 d . . . . .
Cl3S Cl 0.2465(3) 0.51172(14) 0.0517(3) 0.1035(11) 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'
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'
N N 0.0311 0.0180 '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 O1 118.9(5) . . ?
O2 S1 N1 107.7(5) . . ?
O1 S1 N1 106.0(4) . . ?
O2 S1 C15 109.1(5) . . ?
O1 S1 C15 107.6(4) . . ?
N1 S1 C15 106.8(4) . . ?
O4 S2 O3 118.4(5) . . ?
O4 S2 N2 106.3(5) . . ?
O3 S2 N2 107.4(4) . . ?
O4 S2 C24 108.1(5) . . ?
O3 S2 C24 108.2(4) . . ?
N2 S2 C24 107.9(4) . . ?
C11 N1 S1 120.5(7) . . ?
C22 N2 S2 120.5(7) . . ?
C2 C1 C6 117.4(8) . . ?
C2 C1 H1B 121.3 . . ?
C6 C1 H1B 121.3 . . ?
C1 C2 C3 122.9(7) . . ?
C1 C2 C11 129.3(8) . . ?
C3 C2 C11 107.8(7) . . ?
C4 C3 C2 120.9(7) . . ?
C4 C3 C13 132.1(8) . . ?
C2 C3 C13 107.0(7) . . ?
C3 C4 C5 117.7(7) . . ?
C3 C4 H4B 121.2 . . ?
C5 C4 H4B 121.2 . . ?
C6 C5 C10 119.6(7) . . ?
C6 C5 C4 120.5(7) . . ?
C10 C5 C4 119.9(7) . . ?
C5 C6 C7 120.4(7) . . ?
C5 C6 C1 120.6(7) . . ?
C7 C6 C1 119.0(8) . . ?
C8 C7 C6 118.8(8) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C7 C8 C9 121.0(7) . . ?
C7 C8 C20 129.8(8) . . ?
C9 C8 C20 109.1(8) . . ?
C8 C9 C10 122.8(8) . . ?
C8 C9 C22 106.8(7) . . ?
C10 C9 C22 130.4(8) . . ?
C9 C10 C5 117.3(8) . . ?
C9 C10 H10A 121.4 . . ?
C5 C10 H10A 121.4 . . ?
N1 C11 C12 130.4(8) . . ?
N1 C11 C2 123.9(8) . . ?
C12 C11 C2 105.6(7) . . ?
C13 C12 C14 133.0(8) . . ?
C13 C12 C11 108.5(7) . . ?
C14 C12 C11 118.3(8) . . ?
C12 C13 C3 111.0(7) . . ?
C12 C13 C30 126.8(7) . . ?
C3 C13 C30 122.1(7) . . ?
C15 C14 C19 117.5(8) . . ?
C15 C14 C12 120.5(8) . . ?
C19 C14 C12 121.9(8) . . ?
C14 C15 C16 124.8(9) . . ?
C14 C15 S1 121.9(7) . . ?
C16 C15 S1 113.2(8) . . ?
C17 C16 C15 116.9(10) . . ?
C17 C16 H16A 121.6 . . ?
C15 C16 H16A 121.6 . . ?
C16 C17 C18 121.7(9) . . ?
C16 C17 H17A 119.2 . . ?
C18 C17 H17A 119.2 . . ?
C17 C18 C19 120.8(9) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C14 C19 C18 118.2(9) . . ?
C14 C19 H19A 120.9 . . ?
C18 C19 H19A 120.9 . . ?
C21 C20 C8 109.2(7) . . ?
C21 C20 C42 131.9(8) . . ?
C8 C20 C42 118.9(8) . . ?
C20 C21 C23 131.5(8) . . ?
C20 C21 C22 108.2(7) . . ?
C23 C21 C22 120.2(8) . . ?
N2 C22 C21 128.7(8) . . ?
N2 C22 C9 124.5(8) . . ?
C21 C22 C9 106.7(7) . . ?
C24 C23 C28 118.4(8) . . ?
C24 C23 C21 119.4(8) . . ?
C28 C23 C21 122.2(8) . . ?
C23 C24 C25 122.4(9) . . ?
C23 C24 S2 121.7(7) . . ?
C25 C24 S2 115.8(8) . . ?
C26 C25 C24 119.9(10) . . ?
C26 C25 H25A 120.1 . . ?
C24 C25 H25A 120.1 . . ?
C25 C26 C27 119.3(9) . . ?
C25 C26 H26A 120.4 . . ?
C27 C26 H26A 120.4 . . ?
C28 C27 C26 120.8(9) . . ?
C28 C27 H27A 119.6 . . ?
C26 C27 H27A 119.6 . . ?
C27 C28 C23 119.2(9) . . ?
C27 C28 H28A 120.4 . . ?
C23 C28 H28A 120.4 . . ?
C31 C30 C35 121.8(8) . . ?
C31 C30 C13 117.9(8) . . ?
C35 C30 C13 120.1(8) . . ?
C30 C31 C32 117.7(9) . . ?
C30 C31 C36 122.1(8) . . ?
C32 C31 C36 120.2(9) . . ?
C31 C32 C33 123.3(9) . . ?
C31 C32 H32A 118.3 . . ?
C33 C32 H32A 118.3 . . ?
C32 C33 C34 116.4(8) . . ?
C32 C33 C38 124.8(9) . . ?
C34 C33 C38 118.8(9) . . ?
C35 C34 C33 122.3(9) . . ?
C35 C34 H34A 118.9 . . ?
C33 C34 H34A 118.9 . . ?
C34 C35 C30 118.4(9) . . ?
C34 C35 C37 120.2(9) . . ?
C30 C35 C37 121.3(8) . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C41 C38 C40 107.5(11) . . ?
C41 C38 C33 110.7(10) . . ?
C40 C38 C33 112.6(10) . . ?
C41 C38 C39 110.3(14) . . ?
C40 C38 C39 107.5(10) . . ?
C33 C38 C39 108.2(11) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C47 C42 C43 120.9(8) . . ?
C47 C42 C20 121.0(8) . . ?
C43 C42 C20 118.0(8) . . ?
C44 C43 C42 117.0(8) . . ?
C44 C43 C48 120.5(8) . . ?
C42 C43 C48 122.6(8) . . ?
C43 C44 C45 123.2(8) . . ?
C43 C44 H44A 118.4 . . ?
C45 C44 H44A 118.4 . . ?
C46 C45 C44 117.9(8) . . ?
C46 C45 C50 122.0(9) . . ?
C44 C45 C50 120.1(8) . . ?
C45 C46 C47 121.5(10) . . ?
C45 C46 H46A 119.3 . . ?
C47 C46 H46A 119.3 . . ?
C42 C47 C46 119.6(8) . . ?
C42 C47 C49 122.5(8) . . ?
C46 C47 C49 118.0(9) . . ?
C43 C48 H48A 109.5 . . ?
C43 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C43 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C52 C50 C53 109.4(10) . . ?
C52 C50 C51 109.1(10) . . ?
C53 C50 C51 107.6(12) . . ?
C52 C50 C45 114.5(10) . . ?
C53 C50 C45 109.1(9) . . ?
C51 C50 C45 106.9(8) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C50 C52 H52A 109.5 . . ?
C50 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C50 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C50 C53 H53A 109.5 . . ?
C50 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C50 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
Cl3S C1S Cl1S 113.2(8) . . ?
Cl3S C1S Cl2S 109.6(7) . . ?
Cl1S C1S Cl2S 111.0(7) . . ?
Cl3S C1S H1SA 107.6 . . ?
Cl1S C1S H1SA 107.6 . . ?
Cl2S C1S H1SA 107.6 . . ?
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
S1 O2 1.411(9) . ?
S1 O1 1.431(8) . ?
S1 N1 1.630(8) . ?
S1 C15 1.787(10) . ?
S2 O4 1.417(9) . ?
S2 O3 1.423(8) . ?
S2 N2 1.647(7) . ?
S2 C24 1.767(9) . ?
N1 C11 1.253(12) . ?
N2 C22 1.262(12) . ?
C1 C2 1.353(11) . ?
C1 C6 1.429(11) . ?
C1 H1B 0.9500 . ?
C2 C3 1.413(12) . ?
C2 C11 1.502(11) . ?
C3 C4 1.370(11) . ?
C3 C13 1.486(10) . ?
C4 C5 1.438(11) . ?
C4 H4B 0.9500 . ?
C5 C6 1.396(11) . ?
C5 C10 1.432(11) . ?
C6 C7 1.414(12) . ?
C7 C8 1.357(12) . ?
C7 H7A 0.9500 . ?
C8 C9 1.378(12) . ?
C8 C20 1.502(11) . ?
C9 C10 1.370(11) . ?
C9 C22 1.502(12) . ?
C10 H10A 0.9500 . ?
C11 C12 1.493(11) . ?
C12 C13 1.348(12) . ?
C12 C14 1.461(11) . ?
C13 C30 1.511(11) . ?
C14 C15 1.356(14) . ?
C14 C19 1.401(12) . ?
C15 C16 1.395(13) . ?
C16 C17 1.339(14) . ?
C16 H16A 0.9500 . ?
C17 C18 1.376(16) . ?
C17 H17A 0.9500 . ?
C18 C19 1.407(14) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.356(13) . ?
C20 C42 1.506(12) . ?
C21 C23 1.481(11) . ?
C21 C22 1.487(12) . ?
C23 C24 1.374(14) . ?
C23 C28 1.407(12) . ?
C24 C25 1.384(13) . ?
C25 C26 1.363(14) . ?
C25 H25A 0.9500 . ?
C26 C27 1.404(15) . ?
C26 H26A 0.9500 . ?
C27 C28 1.394(13) . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?
C30 C31 1.385(12) . ?
C30 C35 1.398(13) . ?
C31 C32 1.384(13) . ?
C31 C36 1.492(14) . ?
C32 C33 1.394(14) . ?
C32 H32A 0.9500 . ?
C33 C34 1.410(13) . ?
C33 C38 1.516(14) . ?
C34 C35 1.374(12) . ?
C34 H34A 0.9500 . ?
C35 C37 1.509(13) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C41 1.498(17) . ?
C38 C40 1.520(16) . ?
C38 C39 1.53(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C47 1.388(14) . ?
C42 C43 1.409(13) . ?
C43 C44 1.392(12) . ?
C43 C48 1.478(14) . ?
C44 C45 1.403(13) . ?
C44 H44A 0.9500 . ?
C45 C46 1.364(13) . ?
C45 C50 1.571(13) . ?
C46 C47 1.403(13) . ?
C46 H46A 0.9500 . ?
C47 C49 1.520(13) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C52 1.481(14) . ?
C50 C53 1.534(15) . ?
C50 C51 1.551(18) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C1S Cl3S 1.726(15) . ?
C1S Cl1S 1.726(13) . ?
C1S Cl2S 1.748(13) . ?
C1S H1SA 1.0000 . ?
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
O2 S1 N1 C11 -126.4(9) . . . . ?
O1 S1 N1 C11 105.4(9) . . . . ?
C15 S1 N1 C11 -9.2(10) . . . . ?
O4 S2 N2 C22 127.6(9) . . . . ?
O3 S2 N2 C22 -104.7(9) . . . . ?
C24 S2 N2 C22 11.7(10) . . . . ?
C6 C1 C2 C3 -3.9(15) . . . . ?
C6 C1 C2 C11 178.1(9) . . . . ?
C1 C2 C3 C4 2.8(16) . . . . ?
C11 C2 C3 C4 -178.9(8) . . . . ?
C1 C2 C3 C13 -177.3(9) . . . . ?
C11 C2 C3 C13 1.1(11) . . . . ?
C2 C3 C4 C5 -0.3(15) . . . . ?
C13 C3 C4 C5 179.8(9) . . . . ?
C3 C4 C5 C6 -0.7(14) . . . . ?
C3 C4 C5 C10 -179.8(9) . . . . ?
C10 C5 C6 C7 -2.5(13) . . . . ?
C4 C5 C6 C7 178.3(9) . . . . ?
C10 C5 C6 C1 178.6(9) . . . . ?
C4 C5 C6 C1 -0.5(13) . . . . ?
C2 C1 C6 C5 2.8(13) . . . . ?
C2 C1 C6 C7 -176.1(9) . . . . ?
C5 C6 C7 C8 0.0(14) . . . . ?
C1 C6 C7 C8 178.9(9) . . . . ?
C6 C7 C8 C9 2.5(15) . . . . ?
C6 C7 C8 C20 -178.7(9) . . . . ?
C7 C8 C9 C10 -2.5(15) . . . . ?
C20 C8 C9 C10 178.4(9) . . . . ?
C7 C8 C9 C22 178.0(9) . . . . ?
C20 C8 C9 C22 -1.1(11) . . . . ?
C8 C9 C10 C5 -0.1(14) . . . . ?
C22 C9 C10 C5 179.3(9) . . . . ?
C6 C5 C10 C9 2.5(14) . . . . ?
C4 C5 C10 C9 -178.3(8) . . . . ?
S1 N1 C11 C12 0.1(16) . . . . ?
S1 N1 C11 C2 -176.8(7) . . . . ?
C1 C2 C11 N1 -5.3(17) . . . . ?
C3 C2 C11 N1 176.4(10) . . . . ?
C1 C2 C11 C12 177.1(10) . . . . ?
C3 C2 C11 C12 -1.1(10) . . . . ?
N1 C11 C12 C13 -176.6(11) . . . . ?
C2 C11 C12 C13 0.7(11) . . . . ?
N1 C11 C12 C14 7.5(16) . . . . ?
C2 C11 C12 C14 -175.1(8) . . . . ?
C14 C12 C13 C3 174.9(9) . . . . ?
C11 C12 C13 C3 -0.1(11) . . . . ?
C14 C12 C13 C30 -4.4(18) . . . . ?
C11 C12 C13 C30 -179.4(9) . . . . ?
C4 C3 C13 C12 179.3(11) . . . . ?
C2 C3 C13 C12 -0.6(11) . . . . ?
C4 C3 C13 C30 -1.4(16) . . . . ?
C2 C3 C13 C30 178.7(9) . . . . ?
C13 C12 C14 C15 -177.2(11) . . . . ?
C11 C12 C14 C15 -2.6(13) . . . . ?
C13 C12 C14 C19 -1.4(17) . . . . ?
C11 C12 C14 C19 173.2(8) . . . . ?
C19 C14 C15 C16 -1.5(15) . . . . ?
C12 C14 C15 C16 174.5(9) . . . . ?
C19 C14 C15 S1 176.2(7) . . . . ?
C12 C14 C15 S1 -7.8(13) . . . . ?
O2 S1 C15 C14 129.6(9) . . . . ?
O1 S1 C15 C14 -100.1(9) . . . . ?
N1 S1 C15 C14 13.4(10) . . . . ?
O2 S1 C15 C16 -52.5(8) . . . . ?
O1 S1 C15 C16 77.8(8) . . . . ?
N1 S1 C15 C16 -168.7(7) . . . . ?
C14 C15 C16 C17 1.7(15) . . . . ?
S1 C15 C16 C17 -176.1(8) . . . . ?
C15 C16 C17 C18 -0.9(16) . . . . ?
C16 C17 C18 C19 -0.1(17) . . . . ?
C15 C14 C19 C18 0.4(14) . . . . ?
C12 C14 C19 C18 -175.5(9) . . . . ?
C17 C18 C19 C14 0.3(16) . . . . ?
C7 C8 C20 C21 -178.3(10) . . . . ?
C9 C8 C20 C21 0.7(11) . . . . ?
C7 C8 C20 C42 2.5(16) . . . . ?
C9 C8 C20 C42 -178.6(9) . . . . ?
C8 C20 C21 C23 -175.9(9) . . . . ?
C42 C20 C21 C23 3.2(19) . . . . ?
C8 C20 C21 C22 0.0(11) . . . . ?
C42 C20 C21 C22 179.2(10) . . . . ?
S2 N2 C22 C21 -3.5(15) . . . . ?
S2 N2 C22 C9 174.8(7) . . . . ?
C20 C21 C22 N2 177.9(10) . . . . ?
C23 C21 C22 N2 -5.6(15) . . . . ?
C20 C21 C22 C9 -0.7(11) . . . . ?
C23 C21 C22 C9 175.8(8) . . . . ?
C8 C9 C22 N2 -177.6(9) . . . . ?
C10 C9 C22 N2 2.9(17) . . . . ?
C8 C9 C22 C21 1.1(10) . . . . ?
C10 C9 C22 C21 -178.4(9) . . . . ?
C20 C21 C23 C24 178.8(11) . . . . ?
C22 C21 C23 C24 3.3(13) . . . . ?
C20 C21 C23 C28 0.0(16) . . . . ?
C22 C21 C23 C28 -175.5(8) . . . . ?
C28 C23 C24 C25 2.1(15) . . . . ?
C21 C23 C24 C25 -176.7(8) . . . . ?
C28 C23 C24 S2 -174.4(7) . . . . ?
C21 C23 C24 S2 6.8(12) . . . . ?
O4 S2 C24 C23 -128.3(8) . . . . ?
O3 S2 C24 C23 102.2(8) . . . . ?
N2 S2 C24 C23 -13.7(9) . . . . ?
O4 S2 C24 C25 55.0(9) . . . . ?
O3 S2 C24 C25 -74.5(9) . . . . ?
N2 S2 C24 C25 169.6(8) . . . . ?
C23 C24 C25 C26 -1.1(15) . . . . ?
S2 C24 C25 C26 175.6(8) . . . . ?
C24 C25 C26 C27 -0.4(16) . . . . ?
C25 C26 C27 C28 1.0(17) . . . . ?
C26 C27 C28 C23 0.0(16) . . . . ?
C24 C23 C28 C27 -1.5(14) . . . . ?
C21 C23 C28 C27 177.3(9) . . . . ?
C12 C13 C30 C31 96.4(11) . . . . ?
C3 C13 C30 C31 -82.8(11) . . . . ?
C12 C13 C30 C35 -78.6(13) . . . . ?
C3 C13 C30 C35 102.1(10) . . . . ?
C35 C30 C31 C32 2.0(13) . . . . ?
C13 C30 C31 C32 -172.9(8) . . . . ?
C35 C30 C31 C36 -179.9(9) . . . . ?
C13 C30 C31 C36 5.1(12) . . . . ?
C30 C31 C32 C33 1.0(14) . . . . ?
C36 C31 C32 C33 -177.1(9) . . . . ?
C31 C32 C33 C34 -3.1(14) . . . . ?
C31 C32 C33 C38 174.3(10) . . . . ?
C32 C33 C34 C35 2.3(14) . . . . ?
C38 C33 C34 C35 -175.3(10) . . . . ?
C33 C34 C35 C30 0.5(14) . . . . ?
C33 C34 C35 C37 176.7(9) . . . . ?
C31 C30 C35 C34 -2.8(13) . . . . ?
C13 C30 C35 C34 172.1(9) . . . . ?
C31 C30 C35 C37 -178.9(9) . . . . ?
C13 C30 C35 C37 -4.1(13) . . . . ?
C32 C33 C38 C41 -122.6(13) . . . . ?
C34 C33 C38 C41 54.7(16) . . . . ?
C32 C33 C38 C40 -2.3(15) . . . . ?
C34 C33 C38 C40 175.0(9) . . . . ?
C32 C33 C38 C39 116.3(12) . . . . ?
C34 C33 C38 C39 -66.3(14) . . . . ?
C21 C20 C42 C47 79.1(15) . . . . ?
C8 C20 C42 C47 -101.9(10) . . . . ?
C21 C20 C42 C43 -103.2(12) . . . . ?
C8 C20 C42 C43 75.9(11) . . . . ?
C47 C42 C43 C44 -1.5(12) . . . . ?
C20 C42 C43 C44 -179.3(8) . . . . ?
C47 C42 C43 C48 178.9(8) . . . . ?
C20 C42 C43 C48 1.1(12) . . . . ?
C42 C43 C44 C45 2.5(12) . . . . ?
C48 C43 C44 C45 -177.9(8) . . . . ?
C43 C44 C45 C46 -1.4(13) . . . . ?
C43 C44 C45 C50 177.3(9) . . . . ?
C44 C45 C46 C47 -0.8(14) . . . . ?
C50 C45 C46 C47 -179.5(9) . . . . ?
C43 C42 C47 C46 -0.5(13) . . . . ?
C20 C42 C47 C46 177.1(9) . . . . ?
C43 C42 C47 C49 179.0(8) . . . . ?
C20 C42 C47 C49 -3.4(13) . . . . ?
C45 C46 C47 C42 1.8(14) . . . . ?
C45 C46 C47 C49 -177.8(9) . . . . ?
C46 C45 C50 C52 -165.8(10) . . . . ?
C44 C45 C50 C52 15.5(13) . . . . ?
C46 C45 C50 C53 -42.8(14) . . . . ?
C44 C45 C50 C53 138.5(11) . . . . ?
C46 C45 C50 C51 73.2(12) . . . . ?
C44 C45 C50 C51 -105.5(11) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.049 0.720 0.194 157 58 ' '
2 0.049 0.280 0.694 156 58 ' '
3 0.550 0.220 0.194 157 58 ' '
4 0.549 0.780 0.694 156 58 ' '
