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#$Date: 2022-11-08 12:19:29 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106017.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_8106017
loop_
_publ_author_name
'Lo, Kong Mun'
'Lee, See Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of
 chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV),
 C13H19ClN2S2Sn
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1309
_journal_page_last               1311
_journal_paper_doi               10.1515/ncrs-2019-0501
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C13 H19 Cl N2 S2 Sn'
_chemical_formula_sum            'C13 H19 Cl N2 S2 Sn'
_chemical_formula_weight         421.56
_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
_cell_angle_alpha                85.344(2)
_cell_angle_beta                 79.508(2)
_cell_angle_gamma                83.832(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5837(2)
_cell_length_b                   9.9458(2)
_cell_length_c                   12.8720(3)
_cell_measurement_reflns_used    15882
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3010
_cell_measurement_theta_min      3.4920
_cell_volume                     822.33(4)
_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-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXS-97 [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     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.499
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    16.127
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0176
_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)+(0.0291P)²+0.2490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2870
_reflns_number_total             2930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0501_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8106017
_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   0.228
_shelx_estimated_absorpt_t_max   0.610
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 0.48439(2) 0.81316(2) 0.39082(2) 0.01348(6) Uani 1 1 d . . . . .
S1 S 0.30756(7) 0.60263(5) 0.42166(4) 0.01538(11) Uani 1 1 d . . . . .
S2 S 0.58283(7) 0.65990(5) 0.21741(4) 0.01759(11) Uani 1 1 d . . . . .
Cl1 Cl 0.34240(8) 0.85991(5) 0.57712(4) 0.02212(12) Uani 1 1 d . . . . .
N1 N 0.3630(3) 0.44530(17) 0.25898(14) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.1508(2) 0.27759(17) 0.15351(14) 0.0148(3) Uani 1 1 d . . . . .
C1 C 0.3015(3) 0.9652(2) 0.31460(18) 0.0197(4) Uani 1 1 d . . . . .
H1A H 0.3901 1.0331 0.2768 0.030 Uiso 1 1 calc R U . . .
H1B H 0.1941 1.0088 0.3676 0.030 Uiso 1 1 calc R U . . .
H1C H 0.2359 0.9240 0.2641 0.030 Uiso 1 1 calc R U . . .
C2 C 0.8031(3) 0.7907(2) 0.40266(18) 0.0222(5) Uani 1 1 d . . . . .
H2A H 0.8852 0.8210 0.3351 0.033 Uiso 1 1 calc R U . . .
H2B H 0.8460 0.6952 0.4196 0.033 Uiso 1 1 calc R U . . .
H2C H 0.8256 0.8454 0.4588 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4135(3) 0.5569(2) 0.29355(17) 0.0149(4) Uani 1 1 d . . . . .
C4 C 0.2111(3) 0.3575(2) 0.32026(17) 0.0194(4) Uani 1 1 d . . . . .
H4A H 0.1415 0.4007 0.3857 0.023 Uiso 1 1 calc R U . . .
H4B H 0.2832 0.2695 0.3408 0.023 Uiso 1 1 calc R U . . .
C5 C 0.0505(3) 0.3345(2) 0.25377(17) 0.0181(4) Uani 1 1 d . . . . .
H5A H -0.0469 0.2717 0.2937 0.022 Uiso 1 1 calc R U . . .
H5B H -0.0302 0.4217 0.2391 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2938(3) 0.3696(2) 0.09272(17) 0.0167(4) Uani 1 1 d . . . . .
H6A H 0.2164 0.4572 0.0760 0.020 Uiso 1 1 calc R U . . .
H6B H 0.3606 0.3303 0.0252 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4592(3) 0.3926(2) 0.15655(18) 0.0196(4) Uani 1 1 d . . . . .
H7A H 0.5439 0.3061 0.1682 0.023 Uiso 1 1 calc R U . . .
H7B H 0.5523 0.4579 0.1164 0.023 Uiso 1 1 calc R U . . .
C8 C 0.0112(3) 0.2269(2) 0.09669(17) 0.0153(4) Uani 1 1 d . . . . .
C9 C -0.1010(3) 0.1189(2) 0.14391(17) 0.0174(4) Uani 1 1 d . . . . .
H9 H -0.0852 0.0827 0.2129 0.021 Uiso 1 1 calc R U . . .
C10 C -0.2348(3) 0.0646(2) 0.09047(19) 0.0212(5) Uani 1 1 d . . . . .
H10 H -0.3096 -0.0087 0.1231 0.025 Uiso 1 1 calc R U . . .
C11 C -0.2603(3) 0.1165(2) -0.01024(18) 0.0225(5) Uani 1 1 d . . . . .
H11 H -0.3528 0.0794 -0.0464 0.027 Uiso 1 1 calc R U . . .
C12 C -0.1495(3) 0.2228(2) -0.05748(18) 0.0216(5) Uani 1 1 d . . . . .
H12 H -0.1660 0.2586 -0.1265 0.026 Uiso 1 1 calc R U . . .
C13 C -0.0139(3) 0.2779(2) -0.00447(17) 0.0180(4) Uani 1 1 d . . . . .
H13 H 0.0617 0.3506 -0.0377 0.022 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
C2 Sn C1 132.18(9) . .
C2 Sn Cl1 97.91(6) . .
C1 Sn Cl1 99.20(6) . .
C2 Sn S1 115.70(6) . .
C1 Sn S1 109.33(6) . .
Cl1 Sn S1 87.655(16) . .
C2 Sn S2 88.15(6) . .
C1 Sn S2 93.66(6) . .
Cl1 Sn S2 155.971(16) . .
S1 Sn S2 68.887(16) . .
C3 S1 Sn 90.68(7) . .
C3 S2 Sn 82.62(7) . .
C3 N1 C7 123.32(17) . .
C3 N1 C4 124.11(18) . .
C7 N1 C4 112.52(16) . .
C8 N2 C6 115.94(17) . .
C8 N2 C5 114.18(15) . .
C6 N2 C5 110.35(16) . .
Sn C1 H1A 109.5 . .
Sn C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
Sn C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
Sn C2 H2A 109.5 . .
Sn C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
Sn C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 S2 122.54(16) . .
N1 C3 S1 119.77(15) . .
S2 C3 S1 117.68(11) . .
N1 C4 C5 109.68(17) . .
N1 C4 H4A 109.7 . .
C5 C4 H4A 109.7 . .
N1 C4 H4B 109.7 . .
C5 C4 H4B 109.7 . .
H4A C4 H4B 108.2 . .
N2 C5 C4 110.82(16) . .
N2 C5 H5A 109.5 . .
C4 C5 H5A 109.5 . .
N2 C5 H5B 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 108.1 . .
N2 C6 C7 109.79(17) . .
N2 C6 H6A 109.7 . .
C7 C6 H6A 109.7 . .
N2 C6 H6B 109.7 . .
C7 C6 H6B 109.7 . .
H6A C6 H6B 108.2 . .
N1 C7 C6 110.56(16) . .
N1 C7 H7A 109.5 . .
C6 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.1 . .
C13 C8 C9 118.79(19) . .
C13 C8 N2 122.63(18) . .
C9 C8 N2 118.56(19) . .
C10 C9 C8 120.4(2) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C11 C10 C9 120.6(2) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C12 C11 C10 119.3(2) . .
C12 C11 H11 120.3 . .
C10 C11 H11 120.3 . .
C11 C12 C13 120.5(2) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C8 C13 C12 120.3(2) . .
C8 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn C2 2.118(2) .
Sn C1 2.121(2) .
Sn Cl1 2.4722(5) .
Sn S1 2.4734(5) .
Sn S2 2.7458(5) .
S1 C3 1.746(2) .
S2 C3 1.714(2) .
N1 C3 1.324(3) .
N1 C7 1.467(3) .
N1 C4 1.474(3) .
N2 C8 1.427(3) .
N2 C6 1.462(3) .
N2 C5 1.466(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C4 C5 1.522(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.524(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C13 1.390(3) .
C8 C9 1.404(3) .
C9 C10 1.386(3) .
C9 H9 0.9500 .
C10 C11 1.388(3) .
C10 H10 0.9500 .
C11 C12 1.386(3) .
C11 H11 0.9500 .
C12 C13 1.397(3) .
C12 H12 0.9500 .
C13 H13 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
C7 N1 C3 S2 5.4(3) . . . .
C4 N1 C3 S2 -177.15(15) . . . .
C7 N1 C3 S1 -174.06(15) . . . .
C4 N1 C3 S1 3.4(3) . . . .
Sn S2 C3 N1 177.29(17) . . . .
Sn S2 C3 S1 -3.23(10) . . . .
Sn S1 C3 N1 -176.95(15) . . . .
Sn S1 C3 S2 3.55(11) . . . .
C3 N1 C4 C5 127.8(2) . . . .
C7 N1 C4 C5 -54.5(2) . . . .
C8 N2 C5 C4 167.58(17) . . . .
C6 N2 C5 C4 -59.7(2) . . . .
N1 C4 C5 N2 56.2(2) . . . .
C8 N2 C6 C7 -168.81(16) . . . .
C5 N2 C6 C7 59.4(2) . . . .
C3 N1 C7 C6 -127.0(2) . . . .
C4 N1 C7 C6 55.3(2) . . . .
N2 C6 C7 N1 -56.9(2) . . . .
C6 N2 C8 C13 -10.6(3) . . . .
C5 N2 C8 C13 119.4(2) . . . .
C6 N2 C8 C9 167.73(17) . . . .
C5 N2 C8 C9 -62.3(2) . . . .
C13 C8 C9 C10 -0.2(3) . . . .
N2 C8 C9 C10 -178.56(18) . . . .
C8 C9 C10 C11 -0.2(3) . . . .
C9 C10 C11 C12 0.4(3) . . . .
C10 C11 C12 C13 -0.2(3) . . . .
C9 C8 C13 C12 0.4(3) . . . .
N2 C8 C13 C12 178.71(18) . . . .
C11 C12 C13 C8 -0.2(3) . . . .
