#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/19/2211907.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211907
loop_
_publ_author_name
'Hanif, Muhammad'
'Ali, Saqib'
'Hussain, Mukhtiar'
'Bhatti, Hussain Moazam'
'Karmazin Brelot, Lydia'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 [2-(Butylamino)cyclopent-1-ene-1-carbodithioato]chlorodiphenyltin(IV)
;
_journal_coeditor_code           NG2173
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m143
_journal_page_last               m145
_journal_paper_doi               10.1107/S1600536806052123
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Sn (C6 H5)2 (C10 H16 N S2) Cl]'
_chemical_formula_moiety         'C22 H26 Cl N S2 Sn'
_chemical_formula_sum            'C22 H26 Cl N S2 Sn'
_chemical_formula_weight         522.70
_chemical_name_systematic
;
[2-(Butylamino)cyclopent-1-ene-1-carbodithioato)chlorodiphenyltin(IV)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                106.457(11)
_cell_angle_beta                 104.555(11)
_cell_angle_gamma                96.053(11)
_cell_formula_units_Z            2
_cell_length_a                   9.4881(9)
_cell_length_b                   11.0779(10)
_cell_length_c                   12.1896(12)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.15
_cell_volume                     1167.6(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8018
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  0.81211
_exptl_absorpt_correction_T_min  0.60675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS in PLATON; Spek, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.982
_refine_diff_density_min         -1.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0275
_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)+(0.0353P)²+2.4792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                3825
_reflns_number_total             4133
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2173.cif
_cod_data_source_block           I
_cod_original_cell_volume        1167.57(19)
_cod_database_code               2211907
_cod_database_fobs_code          2211907
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 -0.1014(4) 0.7518(4) 0.6905(3) 0.0296(6) Uani d . 1
C C2 -0.1691(4) 0.6598(4) 0.5802(4) 0.0369(9) Uani d . 1
H H2A -0.1107 0.6093 0.5403 0.044 Uiso calc R 1
C C3 -0.3212(5) 0.6396(5) 0.5266(5) 0.0535(12) Uani d . 1
H H3A -0.3661 0.5755 0.4511 0.064 Uiso calc R 1
C C4 -0.4061(5) 0.7130(6) 0.5834(5) 0.0621(15) Uani d . 1
H H4A -0.5101 0.6990 0.5474 0.074 Uiso calc R 1
C C5 -0.3407(6) 0.8066(6) 0.6924(5) 0.0629(16) Uani d . 1
H H5A -0.4000 0.8572 0.7310 0.075 Uiso calc R 1
C C6 -0.1882(5) 0.8278(5) 0.7468(4) 0.0448(11) Uani d . 1
H H6A -0.1436 0.8934 0.8215 0.054 Uiso calc R 1
C C7 0.2741(4) 0.9572(4) 0.8403(3) 0.0296(6) Uani d . 1
C C8 0.2875(6) 1.0486(5) 0.9486(4) 0.0570(13) Uani d . 1
H H8A 0.2334 1.0293 0.9993 0.068 Uiso calc R 1
C C9 0.3783(7) 1.1676(5) 0.9844(5) 0.0642(15) Uani d . 1
H H9A 0.3860 1.2291 1.0591 0.077 Uiso calc R 1
C C10 0.4570(5) 1.1967(5) 0.9126(5) 0.0510(12) Uani d . 1
H H10A 0.5192 1.2784 0.9370 0.061 Uiso calc R 1
C C11 0.4456(5) 1.1073(5) 0.8050(5) 0.0543(12) Uani d . 1
H H11A 0.5001 1.1272 0.7548 0.065 Uiso calc R 1
C C12 0.3546(5) 0.9878(5) 0.7692(4) 0.0424(10) Uani d . 1
H H12A 0.3480 0.9264 0.6948 0.051 Uiso calc R 1
C C13 0.1570(4) 0.6669(4) 0.9878(3) 0.0288(8) Uani d . 1
C C14 0.1887(4) 0.6103(4) 1.0764(3) 0.0288(8) Uani d . 1
C C15 0.1612(4) 0.6504(4) 1.1891(3) 0.0358(9) Uani d . 1
C C16 0.2188(5) 0.5675(5) 1.2626(4) 0.0453(11) Uani d . 1
H H16B 0.1366 0.5052 1.2635 0.054 Uiso calc R 1
H H16A 0.2739 0.6203 1.3459 0.054 Uiso calc R 1
C C17 0.3212(6) 0.4992(6) 1.1991(4) 0.0568(13) Uani d . 1
H H17B 0.3188 0.4117 1.2051 0.068 Uiso calc R 1
H H17A 0.4246 0.5475 1.2345 0.068 Uiso calc R 1
C C18 0.2615(5) 0.4935(4) 1.0684(4) 0.0390(9) Uani d . 1
H H18B 0.3430 0.4986 1.0317 0.047 Uiso calc R 1
H H18A 0.1884 0.4135 1.0209 0.047 Uiso calc R 1
C C19 0.0545(7) 0.7843(5) 1.3418(4) 0.0581(14) Uani d . 1
H H19A 0.0866 0.7246 1.3872 0.070 Uiso calc R 1
C C20 0.1367(7) 0.9137(6) 1.4133(5) 0.0670(16) Uani d . 1
H H20B 0.1147 0.9378 1.4911 0.080 Uiso calc R 1
H H20A 0.1009 0.9743 1.3715 0.080 Uiso calc R 1
C C21 0.3002(7) 0.9282(7) 1.4364(5) 0.0712(16) Uani d . 1
H H21A 0.3239 0.9127 1.3604 0.107 Uiso calc R 1
H H21B 0.3364 0.8662 1.4748 0.107 Uiso calc R 1
H H21C 0.3481 1.0153 1.4891 0.107 Uiso calc R 1
C C22 -0.1182(6) 0.7713(6) 1.3140(5) 0.0609(14) Uani d . 1
H H22C -0.1436 0.7989 1.3892 0.091 Uiso calc R 1
H H22B -0.1660 0.6817 1.2700 0.091 Uiso calc R 1
H H22A -0.1528 0.8252 1.2654 0.091 Uiso calc R 1
N N1 0.0919(5) 0.7438(4) 1.2269(3) 0.0492(10) Uani d . 1
H H1 0.0643 0.7877 1.1780 0.059 Uiso calc R 1
S S1 0.07650(11) 0.80017(10) 0.99417(8) 0.0340(2) Uani d . 1
S S2 0.20321(10) 0.60052(10) 0.85539(8) 0.0314(2) Uani d . 1
Cl Cl1 0.20539(11) 0.67447(10) 0.60336(8) 0.0372(2) Uani d . 1
Sn Sn1 0.12866(2) 0.77481(2) 0.780576(19) 0.02534(10) Uani d . 1
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'
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'
Sn Sn -0.6537 1.4246 '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_publ_flag
C2 C1 C6 118.8(4) ?
C2 C1 Sn1 121.9(3) ?
C6 C1 Sn1 119.3(3) ?
C1 C2 C3 121.2(4) ?
C1 C2 H2A 119.4 ?
C3 C2 H2A 119.4 ?
C4 C3 C2 119.7(5) ?
C4 C3 H3A 120.2 ?
C2 C3 H3A 120.2 ?
C3 C4 C5 120.1(4) ?
C3 C4 H4A 119.9 ?
C5 C4 H4A 119.9 ?
C4 C5 C6 120.7(5) ?
C4 C5 H5A 119.7 ?
C6 C5 H5A 119.7 ?
C5 C6 C1 119.5(5) ?
C5 C6 H6A 120.2 ?
C1 C6 H6A 120.2 ?
C12 C7 C8 118.0(4) ?
C12 C7 Sn1 120.2(3) ?
C8 C7 Sn1 121.8(3) ?
C7 C8 C9 121.2(4) ?
C7 C8 H8A 119.4 ?
C9 C8 H8A 119.4 ?
C10 C9 C8 120.1(5) ?
C10 C9 H9A 119.9 ?
C8 C9 H9A 119.9 ?
C9 C10 C11 119.6(5) ?
C9 C10 H10A 120.2 ?
C11 C10 H10A 120.2 ?
C10 C11 C12 120.3(4) ?
C10 C11 H11A 119.9 ?
C12 C11 H11A 119.9 ?
C7 C12 C11 120.8(4) ?
C7 C12 H12A 119.6 ?
C11 C12 H12A 119.6 ?
C14 C13 S1 126.1(3) ?
C14 C13 S2 118.5(3) ?
S1 C13 S2 115.5(2) ?
C13 C14 C15 126.7(4) ?
C13 C14 C18 124.7(3) ?
C15 C14 C18 108.5(3) ?
N1 C15 C14 126.8(3) ?
N1 C15 C16 122.9(4) ?
C14 C15 C16 110.3(4) ?
C15 C16 C17 103.9(3) ?
C15 C16 H16B 111.0 ?
C17 C16 H16B 111.0 ?
C15 C16 H16A 111.0 ?
C17 C16 H16A 111.0 ?
H16B C16 H16A 109.0 ?
C16 C17 C18 105.3(4) ?
C16 C17 H17B 110.7 ?
C18 C17 H17B 110.7 ?
C16 C17 H17A 110.7 ?
C18 C17 H17A 110.7 ?
H17B C17 H17A 108.8 ?
C14 C18 C17 103.7(4) ?
C14 C18 H18B 111.0 ?
C17 C18 H18B 111.0 ?
C14 C18 H18A 111.0 ?
C17 C18 H18A 111.0 ?
H18B C18 H18A 109.0 ?
C20 C19 N1 109.5(4) ?
C20 C19 C22 113.7(5) ?
N1 C19 C22 109.0(4) ?
C20 C19 H19A 108.2 ?
N1 C19 H19A 108.2 ?
C22 C19 H19A 108.2 ?
C19 C20 C21 114.1(5) ?
C19 C20 H20B 108.7 ?
C21 C20 H20B 108.7 ?
C19 C20 H20A 108.7 ?
C21 C20 H20A 108.7 ?
H20B C20 H20A 107.6 ?
C20 C21 H21A 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C20 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C19 C22 H22C 109.5 ?
C19 C22 H22B 109.5 ?
H22C C22 H22B 109.5 ?
C19 C22 H22A 109.5 ?
H22C C22 H22A 109.5 ?
H22B C22 H22A 109.5 ?
C15 N1 C19 128.3(4) ?
C15 N1 H1 115.9 ?
C19 N1 H1 115.9 ?
C13 S1 Sn1 83.73(12) ?
C13 S2 Sn1 91.38(13) ?
C1 Sn1 C7 121.10(14) y
C1 Sn1 S2 116.28(11) y
C7 Sn1 S2 120.92(10) y
C1 Sn1 Cl1 97.18(10) y
C7 Sn1 Cl1 97.93(10) y
S2 Sn1 Cl1 87.67(3) y
C1 Sn1 S1 92.31(10) y
C7 Sn1 S1 95.10(10) y
S2 Sn1 S1 69.22(3) y
Cl1 Sn1 S1 156.87(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.382(6) ?
C1 C6 1.401(6) ?
C1 Sn1 2.134(4) y
C2 C3 1.391(6) ?
C2 H2A 0.9500 ?
C3 C4 1.374(8) ?
C3 H3A 0.9500 ?
C4 C5 1.376(9) ?
C4 H4A 0.9500 ?
C5 C6 1.395(7) ?
C5 H5A 0.9500 ?
C6 H6A 0.9500 ?
C7 C12 1.376(5) ?
C7 C8 1.384(6) ?
C7 Sn1 2.143(4) y
C8 C9 1.385(7) ?
C8 H8A 0.9500 ?
C9 C10 1.366(7) ?
C9 H9A 0.9500 ?
C10 C11 1.372(7) ?
C10 H10A 0.9500 ?
C11 C12 1.389(7) ?
C11 H11A 0.9500 ?
C12 H12A 0.9500 ?
C13 C14 1.383(5) ?
C13 S1 1.724(4) ?
C13 S2 1.757(4) ?
C14 C15 1.418(5) ?
C14 C18 1.521(6) ?
C15 N1 1.318(6) ?
C15 C16 1.507(5) ?
C16 C17 1.523(7) ?
C16 H16B 0.9900 ?
C16 H16A 0.9900 ?
C17 C18 1.531(6) ?
C17 H17B 0.9900 ?
C17 H17A 0.9900 ?
C18 H18B 0.9900 ?
C18 H18A 0.9900 ?
C19 C20 1.462(8) ?
C19 N1 1.489(5) ?
C19 C22 1.569(8) ?
C19 H19A 1.0000 ?
C20 C21 1.489(8) ?
C20 H20B 0.9900 ?
C20 H20A 0.9900 ?
C21 H21A 0.9800 ?
C21 H21B 0.9800 ?
C21 H21C 0.9800 ?
C22 H22C 0.9800 ?
C22 H22B 0.9800 ?
C22 H22A 0.9800 ?
N1 H1 0.8800 ?
S1 Sn1 2.7139(9) y
S2 Sn1 2.4538(10) y
Cl1 Sn1 2.4562(9) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 S1 . 0.88 2.31 3.045(3) 140.6
C19 H19A Cl1 1_556 1.00 2.83 3.737(5) 152
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
C6 C1 C2 C3 -1.7(6)
Sn1 C1 C2 C3 175.2(3)
C1 C2 C3 C4 0.5(7)
C2 C3 C4 C5 0.5(8)
C3 C4 C5 C6 -0.3(8)
C4 C5 C6 C1 -0.9(8)
C2 C1 C6 C5 1.9(6)
Sn1 C1 C6 C5 -175.2(4)
C12 C7 C8 C9 0.4(8)
Sn1 C7 C8 C9 -178.0(4)
C7 C8 C9 C10 -0.1(9)
C8 C9 C10 C11 -0.1(9)
C9 C10 C11 C12 0.0(8)
C8 C7 C12 C11 -0.6(7)
Sn1 C7 C12 C11 177.9(4)
C10 C11 C12 C7 0.4(8)
S1 C13 C14 C15 0.1(6)
S2 C13 C14 C15 179.4(3)
S1 C13 C14 C18 -179.3(3)
S2 C13 C14 C18 0.1(5)
C13 C14 C15 N1 4.7(7)
C18 C14 C15 N1 -175.9(4)
C13 C14 C15 C16 -177.1(4)
C18 C14 C15 C16 2.3(5)
N1 C15 C16 C17 -166.2(5)
C14 C15 C16 C17 15.5(5)
C15 C16 C17 C18 -26.9(5)
C13 C14 C18 C17 160.4(4)
C15 C14 C18 C17 -19.0(5)
C16 C17 C18 C14 28.2(5)
N1 C19 C20 C21 -55.6(6)
C22 C19 C20 C21 -177.8(4)
C14 C15 N1 C19 176.7(5)
C16 C15 N1 C19 -1.3(8)
C20 C19 N1 C15 114.8(6)
C22 C19 N1 C15 -120.3(5)
C14 C13 S1 Sn1 175.1(3)
S2 C13 S1 Sn1 -4.19(18)
C14 C13 S2 Sn1 -174.8(3)
S1 C13 S2 Sn1 4.61(19)
C2 C1 Sn1 C7 126.1(3)
C6 C1 Sn1 C7 -57.0(4)
C2 C1 Sn1 S2 -68.6(3)
C6 C1 Sn1 S2 108.3(3)
C2 C1 Sn1 Cl1 22.3(3)
C6 C1 Sn1 Cl1 -160.8(3)
C2 C1 Sn1 S1 -136.5(3)
C6 C1 Sn1 S1 40.4(3)
C12 C7 Sn1 C1 -94.3(3)
C8 C7 Sn1 C1 84.1(4)
C12 C7 Sn1 S2 101.1(3)
C8 C7 Sn1 S2 -80.5(4)
C12 C7 Sn1 Cl1 9.1(3)
C8 C7 Sn1 Cl1 -172.6(4)
C12 C7 Sn1 S1 169.9(3)
C8 C7 Sn1 S1 -11.7(4)
C13 S2 Sn1 C1 -84.82(16)
C13 S2 Sn1 C7 80.48(16)
C13 S2 Sn1 Cl1 178.32(12)
C13 S2 Sn1 S1 -2.83(12)
C13 S1 Sn1 C1 120.20(16)
C13 S1 Sn1 C7 -118.30(15)
C13 S1 Sn1 S2 2.90(12)
C13 S1 Sn1 Cl1 5.83(16)
