#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/13/2221307.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_2221307
loop_
_publ_author_name
'Delgado D., Jorge A.'
'Okio, Coco K. Y. A.'
'Welter, Richard'
_publ_section_title
;
 (3-Anilino-1-phenyliminothioureato)chloridodimethyltin(IV)
;
_journal_coeditor_code           BX2197
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m426
_journal_paper_doi               10.1107/S160053680900988X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Sn (C H3)2 (C13 H11 N4 S) Cl]'
_chemical_formula_moiety         'C15 H17 Cl N4 S Sn'
_chemical_formula_sum            'C15 H17 Cl N4 S Sn'
_chemical_formula_weight         439.53
_chemical_name_systematic
;
(3-Anilino-1-phenyliminothioureato)chloridodimethyltin(IV)
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2b'
_symmetry_space_group_name_H-M   'P b n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6850(2)
_cell_length_b                   14.8920(5)
_cell_length_c                   20.6790(7)
_cell_measurement_reflns_used    14356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3598.42(18)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       π
_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  0.1150
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25644
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.129
_refine_diff_density_min         -1.843
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.07P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                2731
_reflns_number_total             4130
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2197.cif
_cod_data_source_block           I
_cod_database_code               2221307
_cod_database_fobs_code          2221307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x, y-1/2, z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn 0.18590(3) 0.56103(2) 0.509606(17) 0.03083(14) Uani d . 1 . .
Cl Cl 0.03058(11) 0.57242(10) 0.59081(6) 0.0489(4) Uani d . 1 . .
S S 0.30578(10) 0.64147(10) 0.58678(6) 0.0440(4) Uani d . 1 . .
N N1 0.3690(3) 0.5795(2) 0.45454(18) 0.0308(9) Uani d . 1 . .
N N2 0.4565(3) 0.6110(3) 0.48494(17) 0.0325(9) Uani d . 1 . .
N N3 0.5342(3) 0.6667(2) 0.57432(18) 0.0343(9) Uani d . 1 . .
N N4 0.5270(3) 0.6917(2) 0.63558(19) 0.0364(9) Uani d . 1 . .
H H4N 0.4606 0.6889 0.6556 0.044 Uiso calc . 1 . .
C C1 0.3037(4) 0.5110(3) 0.3553(2) 0.0368(11) Uani d . 1 . .
H H1 0.2316 0.5011 0.3754 0.044 Uiso calc . 1 . .
C C2 0.3220(4) 0.4841(3) 0.2918(3) 0.0444(13) Uani d . 1 . .
H H2 0.2620 0.4559 0.2683 0.053 Uiso calc . 1 . .
C C3 0.4263(5) 0.4979(3) 0.2626(2) 0.0516(14) Uani d . 1 . .
H H3 0.4380 0.4797 0.2191 0.062 Uiso calc . 1 . .
C C4 0.5137(5) 0.5383(4) 0.2966(3) 0.0484(14) Uani d . 1 . .
H H4 0.5856 0.5474 0.2761 0.058 Uiso calc . 1 . .
C C5 0.4985(4) 0.5659(3) 0.3598(2) 0.0364(11) Uani d . 1 . .
H H5 0.5595 0.5934 0.3829 0.044 Uiso calc . 1 . .
C C6 0.3923(4) 0.5527(3) 0.3896(2) 0.0316(10) Uani d . 1 . .
C C7 0.6144(4) 0.7333(3) 0.7357(2) 0.0423(13) Uani d . 1 . .
H H7 0.5451 0.7188 0.7573 0.051 Uiso calc . 1 . .
C C8 0.7073(5) 0.7652(3) 0.7698(3) 0.0474(14) Uani d . 1 . .
H H8 0.7011 0.7735 0.8152 0.057 Uiso calc . 1 . .
C C9 0.8086(4) 0.7852(4) 0.7392(3) 0.0503(14) Uani d . 1 . .
H H9 0.8718 0.8075 0.7633 0.060 Uiso calc . 1 . .
C C10 0.8178(4) 0.7729(4) 0.6738(3) 0.0518(15) Uani d . 1 . .
H H10 0.8884 0.7856 0.6529 0.062 Uiso calc . 1 . .
C C11 0.7263(5) 0.7424(3) 0.6376(3) 0.0425(13) Uani d . 1 . .
H H11 0.7330 0.7351 0.5921 0.051 Uiso calc . 1 . .
C C12 0.6243(4) 0.7226(3) 0.6692(2) 0.0342(11) Uani d . 1 . .
C C13 0.4384(4) 0.6391(3) 0.5470(2) 0.0329(10) Uani d . 1 . .
C C14 0.2130(5) 0.4204(4) 0.5157(3) 0.0438(14) Uani d . 1 . .
H H14A 0.1517 0.3890 0.4926 0.066 Uiso calc . 1 . .
H H14B 0.2129 0.4019 0.5612 0.066 Uiso calc . 1 . .
H H14C 0.2869 0.4053 0.4961 0.066 Uiso calc . 1 . .
C C15 0.1051(3) 0.6462(3) 0.4410(2) 0.0374(11) Uani d . 1 . .
H H15A 0.0860 0.6115 0.4022 0.056 Uiso calc . 1 . .
H H15B 0.1572 0.6952 0.4293 0.056 Uiso calc . 1 . .
H H15C 0.0350 0.6712 0.4598 0.056 Uiso calc . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 Sn C15 . . 134.0(2) ?
C14 Sn S . . 111.14(15) ?
C15 Sn S . . 113.52(14) ?
C14 Sn N1 . . 90.45(17) ?
C15 Sn N1 . . 90.60(14) ?
S Sn N1 . . 75.30(9) ?
C14 Sn Cl . . 97.86(15) ?
C15 Sn Cl . . 94.95(13) ?
S Sn Cl . . 86.77(4) ?
N1 Sn Cl . . 161.98(9) ?
C13 S Sn . . 100.99(16) ?
N2 N1 C6 . . 114.2(4) ?
N2 N1 Sn . . 120.6(3) ?
C6 N1 Sn . . 125.1(3) ?
N1 N2 C13 . . 116.6(4) ?
C13 N3 N4 . . 116.3(4) ?
N3 N4 C12 . . 120.8(4) ?
N3 N4 H4N . . 119.6 ?
C12 N4 H4N . . 119.6 ?
C2 C1 C6 . . 119.5(4) ?
C2 C1 H1 . . 120.3 ?
C6 C1 H1 . . 120.3 ?
C3 C2 C1 . . 120.5(5) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C2 C3 C4 . . 120.0(5) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 121.1(5) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 119.2(5) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C5 C6 C1 . . 119.8(4) ?
C5 C6 N1 . . 122.9(4) ?
C1 C6 N1 . . 117.3(4) ?
C8 C7 C12 . . 118.8(5) ?
C8 C7 H7 . . 120.6 ?
C12 C7 H7 . . 120.6 ?
C9 C8 C7 . . 121.1(5) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C10 C9 C8 . . 119.5(5) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 121.3(5) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C12 . . 118.5(5) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
C7 C12 C11 . . 120.8(4) ?
C7 C12 N4 . . 117.3(4) ?
C11 C12 N4 . . 121.9(4) ?
N3 C13 N2 . . 111.5(4) ?
N3 C13 S . . 122.8(4) ?
N2 C13 S . . 125.7(3) ?
Sn C14 H14A . . 109.5 ?
Sn C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
Sn C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
Sn C15 H15A . . 109.5 ?
Sn C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
Sn C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sn C14 . 2.122(5) ?
Sn C15 . 2.125(5) ?
Sn S . 2.4380(13) ?
Sn N1 . 2.439(4) ?
Sn Cl . 2.4784(13) ?
S C13 . 1.755(4) ?
N1 N2 . 1.289(5) ?
N1 C6 . 1.428(6) ?
N2 C13 . 1.366(6) ?
N3 C13 . 1.320(5) ?
N3 N4 . 1.323(5) ?
N4 C12 . 1.410(6) ?
N4 H4N . 0.8800 ?
C1 C2 . 1.390(7) ?
C1 C6 . 1.400(6) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.375(7) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.377(7) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(7) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.399(6) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.379(7) ?
C7 C12 . 1.388(7) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.375(8) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.370(8) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.382(7) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.392(7) ?
C11 H11 . 0.9500 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 Sn S C13 . . . . 77.8(2) ?
C15 Sn S C13 . . . . -91.0(2) ?
N1 Sn S C13 . . . . -6.86(18) ?
Cl Sn S C13 . . . . 175.02(17) ?
C14 Sn N1 N2 . . . . -104.0(3) ?
C15 Sn N1 N2 . . . . 121.9(3) ?
S Sn N1 N2 . . . . 7.7(3) ?
Cl Sn N1 N2 . . . . 13.8(5) ?
C14 Sn N1 C6 . . . . 71.9(3) ?
C15 Sn N1 C6 . . . . -62.1(3) ?
S Sn N1 C6 . . . . -176.3(3) ?
Cl Sn N1 C6 . . . . -170.2(2) ?
C6 N1 N2 C13 . . . . 179.0(4) ?
Sn N1 N2 C13 . . . . -4.6(5) ?
C13 N3 N4 C12 . . . . -179.8(4) ?
C6 C1 C2 C3 . . . . 0.2(7) ?
C1 C2 C3 C4 . . . . 0.3(8) ?
C2 C3 C4 C5 . . . . -0.3(8) ?
C3 C4 C5 C6 . . . . -0.3(7) ?
C4 C5 C6 C1 . . . . 0.8(7) ?
C4 C5 C6 N1 . . . . -179.6(4) ?
C2 C1 C6 C5 . . . . -0.8(7) ?
C2 C1 C6 N1 . . . . 179.6(4) ?
N2 N1 C6 C5 . . . . -4.7(6) ?
Sn N1 C6 C5 . . . . 179.1(3) ?
N2 N1 C6 C1 . . . . 174.9(4) ?
Sn N1 C6 C1 . . . . -1.3(5) ?
C12 C7 C8 C9 . . . . -0.8(7) ?
C7 C8 C9 C10 . . . . -0.3(8) ?
C8 C9 C10 C11 . . . . 1.3(9) ?
C9 C10 C11 C12 . . . . -1.2(8) ?
C8 C7 C12 C11 . . . . 1.0(7) ?
C8 C7 C12 N4 . . . . -178.6(4) ?
C10 C11 C12 C7 . . . . 0.0(7) ?
C10 C11 C12 N4 . . . . 179.6(5) ?
N3 N4 C12 C7 . . . . -169.6(4) ?
N3 N4 C12 C11 . . . . 10.9(7) ?
N4 N3 C13 N2 . . . . -177.1(4) ?
N4 N3 C13 S . . . . 4.1(6) ?
N1 N2 C13 N3 . . . . 177.5(4) ?
N1 N2 C13 S . . . . -3.8(6) ?
Sn S C13 N3 . . . . -172.3(4) ?
Sn S C13 N2 . . . . 9.1(4) ?
