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#$Date: 2022-05-13 11:31:04 +0300 (Fri, 13 May 2022) $
#$Revision: 275401 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105246.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_8105246
loop_
_publ_author_name
'Lo, Kong Mun'
'Mun, Lee See'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of (N-benzyl-N-methyl-dithiocarbamato-κ2
 S,S′)di(4-chlorobenzyl)chloridotin(IV), C23H22Cl3NS2Sn
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              647
_journal_page_last               649
_journal_paper_doi               10.1515/ncrs-2019-0881
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C23 H22 Cl3 N S2 Sn'
_chemical_formula_sum            'C23 H22 Cl3 N S2 Sn'
_chemical_formula_weight         601.57
_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_method           SHELXL-2018/3
_cell_angle_alpha                99.4270(10)
_cell_angle_beta                 94.2470(10)
_cell_angle_gamma                95.8170(10)
_cell_formula_units_Z            2
_cell_length_a                   9.39540(10)
_cell_length_b                   10.27470(10)
_cell_length_c                   12.8743(2)
_cell_measurement_reflns_used    22327
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3670
_cell_measurement_theta_min      3.4770
_cell_volume                     1214.51(3)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28919
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.495
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    13.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0167
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0262P)²+0.4558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0446
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4229
_reflns_number_total             4335
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0881_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8105246
_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   0.269
_shelx_estimated_absorpt_t_max   0.616
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
Sn Sn 0.24001(2) 0.67949(2) 0.82179(2) 0.01528(5) Uani 1 1 d . . . . .
Cl1 Cl 0.42842(5) 0.69311(4) 0.96736(3) 0.02267(9) Uani 1 1 d . . . . .
Cl2 Cl 0.36285(6) 0.01355(4) 0.62114(4) 0.03407(12) Uani 1 1 d . . . . .
Cl3 Cl 0.20085(7) 1.01771(5) 1.34520(4) 0.03782(13) Uani 1 1 d . . . . .
S1 S 0.43335(4) 0.65898(4) 0.70412(3) 0.01776(9) Uani 1 1 d . . . . .
S2 S 0.13574(4) 0.67298(4) 0.61763(3) 0.01996(9) Uani 1 1 d . . . . .
N1 N 0.36586(15) 0.68606(14) 0.50664(11) 0.0160(3) Uani 1 1 d . . . . .
C1 C 0.31362(18) 0.67438(16) 0.59734(13) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.51936(19) 0.68462(19) 0.49239(14) 0.0215(4) Uani 1 1 d . . . . .
H2A H 0.569578 0.774152 0.516010 0.032 Uiso 1 1 calc R U . . .
H2B H 0.531261 0.655538 0.417477 0.032 Uiso 1 1 calc R U . . .
H2C H 0.559676 0.623222 0.534183 0.032 Uiso 1 1 calc R U . . .
C3 C 0.27602(19) 0.70873(17) 0.41364(14) 0.0186(3) Uani 1 1 d . . . . .
H3A H 0.321485 0.786129 0.386580 0.022 Uiso 1 1 calc R U . . .
H3B H 0.180586 0.729327 0.434973 0.022 Uiso 1 1 calc R U . . .
C4 C 0.25738(18) 0.58852(17) 0.32702(13) 0.0173(3) Uani 1 1 d . . . . .
C5 C 0.20382(18) 0.46468(17) 0.34761(14) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.176170 0.456276 0.415922 0.022 Uiso 1 1 calc R U . . .
C6 C 0.19080(19) 0.35366(18) 0.26856(15) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.153498 0.269527 0.282662 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2323(2) 0.36537(19) 0.16871(15) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.225058 0.289033 0.115001 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2840(2) 0.4883(2) 0.14776(14) 0.0243(4) Uani 1 1 d . . . . .
H8 H 0.311027 0.496480 0.079270 0.029 Uiso 1 1 calc R U . . .
C9 C 0.29650(19) 0.59963(19) 0.22639(14) 0.0215(4) Uani 1 1 d . . . . .
H9 H 0.331945 0.683878 0.211488 0.026 Uiso 1 1 calc R U . . .
C10 C 0.12043(19) 0.49561(17) 0.84102(14) 0.0185(3) Uani 1 1 d . . . . .
H10A H 0.121080 0.491312 0.917315 0.022 Uiso 1 1 calc R U . . .
H10B H 0.019339 0.493652 0.812396 0.022 Uiso 1 1 calc R U . . .
C11 C 0.18183(18) 0.37702(17) 0.78584(14) 0.0171(3) Uani 1 1 d . . . . .
C12 C 0.28872(19) 0.31930(17) 0.83693(14) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.324379 0.357114 0.907542 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3443(2) 0.20765(17) 0.78689(15) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.417665 0.169818 0.822546 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2912(2) 0.15261(17) 0.68443(15) 0.0219(4) Uani 1 1 d . . . . .
C15 C 0.1855(2) 0.20781(18) 0.63070(14) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.149900 0.169068 0.560262 0.027 Uiso 1 1 calc R U . . .
C16 C 0.13256(19) 0.32016(18) 0.68117(14) 0.0198(4) Uani 1 1 d . . . . .
H16 H 0.061669 0.359349 0.644204 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1694(2) 0.87214(18) 0.87071(15) 0.0237(4) Uani 1 1 d . . . . .
H17A H 0.229918 0.939862 0.841977 0.028 Uiso 1 1 calc R U . . .
H17B H 0.068989 0.871132 0.840847 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1775(2) 0.90998(17) 0.98866(14) 0.0197(4) Uani 1 1 d . . . . .
C19 C 0.2908(2) 0.99686(18) 1.04470(16) 0.0248(4) Uani 1 1 d . . . . .
H19 H 0.363634 1.034308 1.007462 0.030 Uiso 1 1 calc R U . . .
C20 C 0.2992(2) 1.02984(18) 1.15419(16) 0.0267(4) Uani 1 1 d . . . . .
H20 H 0.377247 1.089089 1.191803 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1929(2) 0.97533(18) 1.20727(15) 0.0246(4) Uani 1 1 d . . . . .
C22 C 0.0783(2) 0.88876(18) 1.15467(16) 0.0259(4) Uani 1 1 d . . . . .
H22 H 0.005375 0.852369 1.192418 0.031 Uiso 1 1 calc R U . . .
C23 C 0.0724(2) 0.85626(18) 1.04539(15) 0.0236(4) Uani 1 1 d . . . . .
H23 H -0.005175 0.795938 1.008360 0.028 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 '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
C10 Sn C17 123.28(7) . .
C10 Sn S1 115.91(5) . .
C17 Sn S1 119.37(6) . .
C10 Sn Cl1 97.98(5) . .
C17 Sn Cl1 97.31(5) . .
S1 Sn Cl1 86.151(14) . .
C10 Sn S2 96.15(5) . .
C17 Sn S2 91.65(5) . .
S1 Sn S2 69.467(13) . .
Cl1 Sn S2 155.323(14) . .
C1 S1 Sn 90.04(6) . .
C1 S2 Sn 82.23(6) . .
C1 N1 C2 122.34(14) . .
C1 N1 C3 122.60(14) . .
C2 N1 C3 114.97(14) . .
N1 C1 S2 124.24(13) . .
N1 C1 S1 118.16(13) . .
S2 C1 S1 117.61(10) . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 C4 111.28(14) . .
N1 C3 H3A 109.4 . .
C4 C3 H3A 109.4 . .
N1 C3 H3B 109.4 . .
C4 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
C5 C4 C9 119.35(16) . .
C5 C4 C3 120.32(15) . .
C9 C4 C3 120.32(16) . .
C6 C5 C4 120.14(17) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C7 120.10(17) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C8 C7 C6 119.87(17) . .
C8 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
C7 C8 C9 120.22(17) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C8 C9 C4 120.31(17) . .
C8 C9 H9 119.8 . .
C4 C9 H9 119.8 . .
C11 C10 Sn 111.99(11) . .
C11 C10 H10A 109.2 . .
Sn C10 H10A 109.2 . .
C11 C10 H10B 109.2 . .
Sn C10 H10B 109.2 . .
H10A C10 H10B 107.9 . .
C12 C11 C16 118.01(16) . .
C12 C11 C10 121.17(16) . .
C16 C11 C10 120.81(16) . .
C13 C12 C11 121.51(16) . .
C13 C12 H12 119.2 . .
C11 C12 H12 119.2 . .
C14 C13 C12 118.91(17) . .
C14 C13 H13 120.5 . .
C12 C13 H13 120.5 . .
C13 C14 C15 121.25(16) . .
C13 C14 Cl2 118.82(15) . .
C15 C14 Cl2 119.91(14) . .
C16 C15 C14 119.13(17) . .
C16 C15 H15 120.4 . .
C14 C15 H15 120.4 . .
C15 C16 C11 121.16(17) . .
C15 C16 H16 119.4 . .
C11 C16 H16 119.4 . .
C18 C17 Sn 112.21(12) . .
C18 C17 H17A 109.2 . .
Sn C17 H17A 109.2 . .
C18 C17 H17B 109.2 . .
Sn C17 H17B 109.2 . .
H17A C17 H17B 107.9 . .
C19 C18 C23 118.16(17) . .
C19 C18 C17 121.32(17) . .
C23 C18 C17 120.51(17) . .
C20 C19 C18 121.16(18) . .
C20 C19 H19 119.4 . .
C18 C19 H19 119.4 . .
C21 C20 C19 118.92(18) . .
C21 C20 H20 120.5 . .
C19 C20 H20 120.5 . .
C20 C21 C22 121.80(18) . .
C20 C21 Cl3 119.46(15) . .
C22 C21 Cl3 118.74(16) . .
C23 C22 C21 118.39(18) . .
C23 C22 H22 120.8 . .
C21 C22 H22 120.8 . .
C22 C23 C18 121.56(17) . .
C22 C23 H23 119.2 . .
C18 C23 H23 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn C10 2.1581(17) .
Sn C17 2.1622(17) .
Sn S1 2.4535(4) .
Sn Cl1 2.4572(4) .
Sn S2 2.7240(4) .
Cl2 C14 1.7476(18) .
Cl3 C21 1.7518(19) .
S1 C1 1.7488(17) .
S2 C1 1.7095(17) .
N1 C1 1.318(2) .
N1 C2 1.468(2) .
N1 C3 1.477(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 C4 1.509(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.394(3) .
C4 C9 1.392(3) .
C5 C6 1.387(3) .
C5 H5 0.9500 .
C6 C7 1.391(3) .
C6 H6 0.9500 .
C7 C8 1.382(3) .
C7 H7 0.9500 .
C8 C9 1.387(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.497(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.394(3) .
C11 C16 1.402(3) .
C12 C13 1.390(3) .
C12 H12 0.9500 .
C13 C14 1.382(3) .
C13 H13 0.9500 .
C14 C15 1.388(3) .
C15 C16 1.386(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C18 1.499(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.390(3) .
C18 C23 1.393(3) .
C19 C20 1.389(3) .
C19 H19 0.9500 .
C20 C21 1.376(3) .
C20 H20 0.9500 .
C21 C22 1.382(3) .
C22 C23 1.387(3) .
C22 H22 0.9500 .
C23 H23 0.9500 .
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
C2 N1 C1 S2 -179.00(13) . . . .
C3 N1 C1 S2 4.4(2) . . . .
C2 N1 C1 S1 0.9(2) . . . .
C3 N1 C1 S1 -175.75(12) . . . .
Sn S2 C1 N1 -172.80(15) . . . .
Sn S2 C1 S1 7.32(8) . . . .
Sn S1 C1 N1 172.06(13) . . . .
Sn S1 C1 S2 -8.05(9) . . . .
C1 N1 C3 C4 -110.78(18) . . . .
C2 N1 C3 C4 72.36(18) . . . .
N1 C3 C4 C5 54.9(2) . . . .
N1 C3 C4 C9 -123.61(17) . . . .
C9 C4 C5 C6 0.5(3) . . . .
C3 C4 C5 C6 -178.11(16) . . . .
C4 C5 C6 C7 0.5(3) . . . .
C5 C6 C7 C8 -1.2(3) . . . .
C6 C7 C8 C9 0.9(3) . . . .
C7 C8 C9 C4 0.1(3) . . . .
C5 C4 C9 C8 -0.8(3) . . . .
C3 C4 C9 C8 177.78(16) . . . .
Sn C10 C11 C12 89.05(17) . . . .
Sn C10 C11 C16 -91.37(17) . . . .
C16 C11 C12 C13 -0.8(3) . . . .
C10 C11 C12 C13 178.76(17) . . . .
C11 C12 C13 C14 -0.5(3) . . . .
C12 C13 C14 C15 0.9(3) . . . .
C12 C13 C14 Cl2 179.20(14) . . . .
C13 C14 C15 C16 -0.1(3) . . . .
Cl2 C14 C15 C16 -178.31(14) . . . .
C14 C15 C16 C11 -1.3(3) . . . .
C12 C11 C16 C15 1.7(3) . . . .
C10 C11 C16 C15 -177.86(16) . . . .
Sn C17 C18 C19 100.42(18) . . . .
Sn C17 C18 C23 -78.17(19) . . . .
C23 C18 C19 C20 -0.2(3) . . . .
C17 C18 C19 C20 -178.83(17) . . . .
C18 C19 C20 C21 -0.2(3) . . . .
C19 C20 C21 C22 0.1(3) . . . .
C19 C20 C21 Cl3 -179.15(14) . . . .
C20 C21 C22 C23 0.4(3) . . . .
Cl3 C21 C22 C23 179.65(14) . . . .
C21 C22 C23 C18 -0.8(3) . . . .
C19 C18 C23 C22 0.7(3) . . . .
C17 C18 C23 C22 179.36(17) . . . .
