#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/55/2225501.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_2225501
loop_
_publ_author_name
'Muthalib, Amirah Faizah'
'Baba, Ibrahim'
'Farina, Yang'
'Ng, Seik Weng'
_publ_section_title
;
 Bis(N-isopropyl-N-methyldithiocarbamato-κ²S,S')diphenyltin(IV)
;
_journal_coeditor_code           CI5039
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m354
_journal_paper_doi               10.1107/S1600536810007415
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Sn (C6 H5)2 (C5 H10 N S2)2]'
_chemical_formula_moiety         'C22 H30 N2 S4 Sn'
_chemical_formula_sum            'C22 H30 N2 S4 Sn'
_chemical_formula_weight         569.41
_chemical_name_systematic
;
Bis(N-isopropyl-N-methyldithiocarbamato-
κ²S,S')diphenyltin(IV)
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            4
_cell_length_a                   18.8797(10)
_cell_length_b                   9.2067(5)
_cell_length_c                   14.5694(8)
_cell_measurement_reflns_used    6898
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.4
_cell_volume                     2532.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15127
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.350
_exptl_absorpt_correction_T_max  0.7740
_exptl_absorpt_correction_T_min  0.6493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+2.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                2291
_reflns_number_total             2785
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5039.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2225501
_cod_database_fobs_code          2225501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn1 0.5000 0.71348(3) 0.2500 0.03365(10) Uani d S 1 . .
S S1 0.44810(4) 0.65957(8) 0.41039(4) 0.04395(18) Uani d . 1 . .
S S2 0.40918(5) 0.48826(9) 0.24740(4) 0.04373(19) Uani d . 1 . .
N N1 0.36739(12) 0.4240(3) 0.41754(14) 0.0388(5) Uani d . 1 . .
C C1 0.42071(15) 0.8630(3) 0.19862(19) 0.0404(6) Uani d . 1 . .
C C2 0.44326(19) 0.9844(4) 0.1519(3) 0.0648(10) Uani d . 1 . .
H H2 0.4911 0.9945 0.1382 0.078 Uiso calc R 1 . .
C C3 0.3962(2) 1.0925(4) 0.1246(3) 0.0802(12) Uani d . 1 . .
H H3 0.4128 1.1745 0.0941 0.096 Uiso calc R 1 . .
C C4 0.3258(2) 1.0776(4) 0.1429(3) 0.0722(11) Uani d . 1 . .
H H4 0.2943 1.1505 0.1258 0.087 Uiso calc R 1 . .
C C5 0.3015(2) 0.9560(4) 0.1861(3) 0.0692(10) Uani d . 1 . .
H H5 0.2533 0.9448 0.1969 0.083 Uiso calc R 1 . .
C C6 0.34853(18) 0.8492(4) 0.2139(2) 0.0544(8) Uani d . 1 . .
H H6 0.3314 0.7668 0.2434 0.065 Uiso calc R 1 . .
C C7 0.40355(14) 0.5130(3) 0.36386(17) 0.0356(5) Uani d . 1 . .
C C8 0.36473(18) 0.4480(4) 0.51766(19) 0.0518(8) Uani d . 1 . .
H H8A 0.4088 0.4889 0.5379 0.078 Uiso calc R 1 . .
H H8B 0.3568 0.3571 0.5482 0.078 Uiso calc R 1 . .
H H8C 0.3268 0.5137 0.5319 0.078 Uiso calc R 1 . .
C C9 0.33678(18) 0.2865(3) 0.3824(2) 0.0486(7) Uani d . 1 . .
H H9 0.3324 0.2958 0.3156 0.058 Uiso calc R 1 . .
C C10 0.2637(2) 0.2584(5) 0.4203(3) 0.0784(12) Uani d . 1 . .
H H10A 0.2425 0.1787 0.3880 0.118 Uiso calc R 1 . .
H H10B 0.2351 0.3437 0.4128 0.118 Uiso calc R 1 . .
H H10C 0.2672 0.2350 0.4844 0.118 Uiso calc R 1 . .
C C11 0.3871(3) 0.1643(5) 0.4012(4) 0.1013(17) Uani d . 1 . .
H H11A 0.3723 0.0795 0.3681 0.152 Uiso calc R 1 . .
H H11B 0.3875 0.1436 0.4658 0.152 Uiso calc R 1 . .
H H11C 0.4339 0.1916 0.3818 0.152 Uiso calc R 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'
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
C1 Sn1 C1 3_655 . 101.13(15) ?
C1 Sn1 S1 3_655 3_655 99.94(8) ?
C1 Sn1 S1 . 3_655 94.10(7) ?
C1 Sn1 S1 3_655 . 94.10(7) ?
C1 Sn1 S1 . . 99.94(8) ?
S1 Sn1 S1 3_655 . 157.84(4) ?
C1 Sn1 S2 3_655 . 159.15(7) ?
C1 Sn1 S2 . . 92.55(8) ?
S1 Sn1 S2 3_655 . 94.64(2) ?
S1 Sn1 S2 . . 67.84(2) ?
C1 Sn1 S2 3_655 3_655 92.55(8) ?
C1 Sn1 S2 . 3_655 159.15(7) ?
S1 Sn1 S2 3_655 3_655 67.84(2) ?
S1 Sn1 S2 . 3_655 94.64(2) ?
S2 Sn1 S2 . 3_655 79.19(4) ?
C7 S1 Sn1 . . 88.84(9) ?
C7 S2 Sn1 . . 85.58(10) ?
C7 N1 C8 . . 120.6(2) ?
C7 N1 C9 . . 121.7(2) ?
C8 N1 C9 . . 117.1(2) ?
C2 C1 C6 . . 117.3(3) ?
C2 C1 Sn1 . . 118.2(2) ?
C6 C1 Sn1 . . 124.4(2) ?
C1 C2 C3 . . 121.7(3) ?
C1 C2 H2 . . 119.2 ?
C3 C2 H2 . . 119.2 ?
C4 C3 C2 . . 119.6(4) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.2(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 121.1(3) ?
C1 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
N1 C7 S2 . . 122.3(2) ?
N1 C7 S1 . . 120.20(19) ?
S2 C7 S1 . . 117.49(15) ?
N1 C8 H8A . . 109.5 ?
N1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 112.1(3) ?
N1 C9 C11 . . 109.3(3) ?
C10 C9 C11 . . 112.6(3) ?
N1 C9 H9 . . 107.5 ?
C10 C9 H9 . . 107.5 ?
C11 C9 H9 . . 107.5 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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
Sn1 C1 3_655 2.167(3) ?
Sn1 C1 . 2.167(3) yes
Sn1 S1 3_655 2.5820(7) ?
Sn1 S1 . 2.5820(7) yes
Sn1 S2 . 2.6910(8) yes
Sn1 S2 3_655 2.6909(8) ?
S1 C7 . 1.728(3) ?
S2 C7 . 1.715(3) ?
N1 C7 . 1.323(3) ?
N1 C8 . 1.476(3) ?
N1 C9 . 1.483(4) ?
C1 C2 . 1.376(4) ?
C1 C6 . 1.387(4) ?
C2 C3 . 1.392(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.362(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.364(6) ?
C4 H4 . 0.93 ?
C5 C6 . 1.386(5) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 C10 . 1.508(5) ?
C9 C11 . 1.498(5) ?
C9 H9 . 0.98 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
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
C1 Sn1 S1 C7 3_655 . . . -166.32(12) ?
C1 Sn1 S1 C7 . . . . 91.61(12) ?
S1 Sn1 S1 C7 3_655 . . . -36.91(9) ?
S2 Sn1 S1 C7 . . . . 2.91(9) ?
S2 Sn1 S1 C7 3_655 . . . -73.43(9) ?
C1 Sn1 S2 C7 3_655 . . . 28.6(2) ?
C1 Sn1 S2 C7 . . . . -102.64(12) ?
S1 Sn1 S2 C7 3_655 . . . 163.03(9) ?
S1 Sn1 S2 C7 . . . . -2.94(9) ?
S2 Sn1 S2 C7 3_655 . . . 96.66(9) ?
C1 Sn1 C1 C2 3_655 . . . 41.2(2) ?
S1 Sn1 C1 C2 3_655 . . . -59.7(3) ?
S1 Sn1 C1 C2 . . . . 137.5(3) ?
S2 Sn1 C1 C2 . . . . -154.6(3) ?
S2 Sn1 C1 C2 3_655 . . . -88.8(3) ?
C1 Sn1 C1 C6 3_655 . . . -135.0(3) ?
S1 Sn1 C1 C6 3_655 . . . 124.0(3) ?
S1 Sn1 C1 C6 . . . . -38.8(3) ?
S2 Sn1 C1 C6 . . . . 29.2(3) ?
S2 Sn1 C1 C6 3_655 . . . 94.9(3) ?
C6 C1 C2 C3 . . . . 2.9(6) ?
Sn1 C1 C2 C3 . . . . -173.6(3) ?
C1 C2 C3 C4 . . . . -1.2(7) ?
C2 C3 C4 C5 . . . . -1.3(7) ?
C3 C4 C5 C6 . . . . 1.9(6) ?
C2 C1 C6 C5 . . . . -2.2(5) ?
Sn1 C1 C6 C5 . . . . 174.0(3) ?
C4 C5 C6 C1 . . . . -0.1(6) ?
C8 N1 C7 S2 . . . . 179.1(2) ?
C9 N1 C7 S2 . . . . 7.8(4) ?
C8 N1 C7 S1 . . . . -0.2(4) ?
C9 N1 C7 S1 . . . . -171.5(2) ?
Sn1 S2 C7 N1 . . . . -174.7(2) ?
Sn1 S2 C7 S1 . . . . 4.59(14) ?
Sn1 S1 C7 N1 . . . . 174.6(2) ?
Sn1 S1 C7 S2 . . . . -4.77(15) ?
C7 N1 C9 C10 . . . . -139.3(3) ?
C8 N1 C9 C10 . . . . 49.2(4) ?
C7 N1 C9 C11 . . . . 95.2(4) ?
C8 N1 C9 C11 . . . . -76.4(4) ?
