#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/42/2004288.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_2004288
loop_
_publ_author_name
'Aupers, J. H.'
'Wardell, J. L.'
_publ_section_title
;
 [4-Chloro-3-(2-nitrophenylthio)butyl]triphenylstannane
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2559
_journal_page_last               2561
_journal_paper_doi               10.1107/S0108270195008110
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C28 H26 Cl1 N1 O2 S Sn1'
_chemical_formula_structural     'C28 H26 Cl1 N1 O2 S1 Sn1'
_chemical_formula_sum            'C28 H26 Cl N O2 S Sn'
_chemical_formula_weight         594.72
_chemical_melting_point          354.6(5)
_chemical_name_systematic
;
[4-chloro-3-(2-nitrophenylthio)butyl]triphenylstannane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           International_Tables_Vol_IV_Table_2.2B
_audit_creation_method           CRYSTALS
_cell_angle_alpha                90.0
_cell_angle_beta                 92.78(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   23.382(6)
_cell_length_b                   10.160(3)
_cell_length_c                   11.265(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      14.86
_cell_measurement_theta_min      13.03
_cell_volume                     2673.0(16)
_computing_data_collection       'CAD-4 Software (Frenz, 1983)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'CAMERON (Pearce, Watkin & Prout, 1992)'
_computing_publication_material  CRYSTALS/PC
_computing_structure_refinement  'CRYSTALS/PC (Watkin et al., 1985)'
_computing_structure_solution    'SIR88 (Burla et al., 1989)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    'not known, data lost'
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4720
_diffrn_reflns_theta_max         24.0
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    1.158
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   'empirical via \y scans (Frenz, 1983)'
_exptl_absorpt_process_details
'ψ scan, 4 reflections, (Enraf-Nonius, 1983)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.48
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.65
_refine_ls_abs_structure_Flack   0
_refine_ls_abs_structure_Rogers  1.0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.934
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2680
_refine_ls_R_factor_obs          0.035
_refine_ls_shift/esd_max         0.012
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
'Weights: five-term Chebychev polynomial (Carruthers & Watkin, 1979)'
_refine_ls_wR_factor_obs         0.042
_reflns_number_observed          2680
_reflns_number_total             4197
_reflns_observed_criterion       >3\s(I)
_cod_data_source_file            mu1188.cif
_cod_data_source_block           aber2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '81-82\% C' was changed to '354.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2673(2)
_cod_original_sg_symbol_H-M      'P  21/c'
_cod_original_formula_sum        'C28 H26 Cl1 N1 O2 S1 Sn1'
_cod_database_code               2004288
loop_
_symmetry_equiv_pos_as_xyz
X,Y,Z
-X,-Y,-Z
-X,Y+1/2,-Z+1/2
X,-Y+1/2,Z+1/2
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Sn(1) 1.0000 0.18338(1) 0.01966(3) 0.11660(3) 0.0558 Uani
Cl(16) 1.0000 0.34310(9) -0.0683(2) 0.4020(2) 0.1013 Uani
S(5) 1.0000 0.37237(7) -0.0908(1) 0.0228(1) 0.0735 Uani
O(9) 1.0000 0.4899(2) 0.0007(5) -0.2444(5) 0.0993 Uani
O(10) 1.0000 0.4311(3) -0.1177(6) -0.1669(6) 0.1214 Uani
N(8) 1.0000 0.4553(2) -0.0169(5) -0.1713(4) 0.0691 Uani
C(2) 1.0000 0.2369(2) -0.1416(5) 0.0639(6) 0.0745 Uani
C(3) 1.0000 0.2858(3) -0.1780(5) 0.1485(6) 0.0733 Uani
C(4) 1.0000 0.3343(2) -0.0751(5) 0.1584(5) 0.0615 Uani
C(6) 1.0000 0.4067(1) 0.0638(2) 0.0042(3) 0.0601 Uani
C(7) 1.0000 0.4434(1) 0.0810(3) -0.0880(3) 0.0593 Uani
C(11) 1.0000 0.4690(1) 0.2026(3) -0.1051(3) 0.0737 Uani
C(12) 1.0000 0.4578(2) 0.3071(3) -0.0300(3) 0.0826 Uani
C(13) 1.0000 0.4212(2) 0.2900(3) 0.0622(3) 0.0757 Uani
C(14) 1.0000 0.3956(1) 0.1683(3) 0.0793(2) 0.0655 Uani
C(15) 1.0000 0.3756(3) -0.0946(6) 0.2625(6) 0.0823 Uani
C(17) 1.0000 0.1367(1) -0.0392(3) 0.2672(2) 0.0593 Uani
C(18) 1.0000 0.1273(2) -0.1712(2) 0.2921(3) 0.0730 Uani
C(19) 1.0000 0.0961(2) -0.2063(2) 0.3891(4) 0.0853 Uani
C(20) 1.0000 0.0742(2) -0.1093(4) 0.4612(3) 0.0775 Uani
C(21) 1.0000 0.0836(2) 0.0228(3) 0.4363(3) 0.0779 Uani
C(22) 1.0000 0.1148(2) 0.0578(2) 0.3393(3) 0.0655 Uani
C(23) 1.0000 0.1246(1) 0.0642(3) -0.0294(2) 0.0576 Uani
C(24) 1.0000 0.0683(1) 0.0995(4) -0.0107(3) 0.0752 Uani
C(25) 1.0000 0.0300(1) 0.1206(4) -0.1072(4) 0.0913 Uani
C(26) 1.0000 0.0480(2) 0.1063(5) -0.2222(3) 0.0965 Uani
C(27) 1.0000 0.1043(2) 0.0710(5) -0.2409(2) 0.0906 Uani
C(28) 1.0000 0.1426(1) 0.0500(4) -0.1445(3) 0.0754 Uani
C(29) 1.0000 0.2278(1) 0.1984(2) 0.1643(2) 0.0521 Uani
C(30) 1.0000 0.2249(2) 0.3052(3) 0.0870(2) 0.0675 Uani
C(31) 1.0000 0.2536(2) 0.4212(3) 0.1172(3) 0.0826 Uani
C(32) 1.0000 0.2852(2) 0.4304(3) 0.2245(3) 0.0815 Uani
C(33) 1.0000 0.2882(1) 0.3236(3) 0.3018(3) 0.0759 Uani
C(34) 1.0000 0.2595(1) 0.2076(3) 0.2716(2) 0.0628 Uani
H(2) 1.0000 0.2532 -0.1175 -0.0136 0.0500 Uiso
H(3) 1.0000 0.2119 -0.2210 0.0527 0.0500 Uiso
H(4) 1.0000 0.3023 -0.2629 0.1213 0.0500 Uiso
H(5) 1.0000 0.2705 -0.1901 0.2291 0.0500 Uiso
H(6) 1.0000 0.3157 0.0084 0.1833 0.0500 Uiso
H(151) 1.0000 0.4081 -0.0311 0.2561 0.0500 Uiso
H(152) 1.0000 0.3907 -0.1866 0.2605 0.0500 Uiso
H(11) 1.0000 0.4954 0.2150 -0.1715 0.0500 Uiso
H(12) 1.0000 0.4762 0.3946 -0.0423 0.0500 Uiso
H(13) 1.0000 0.4131 0.3651 0.1163 0.0500 Uiso
H(14) 1.0000 0.3692 0.1560 0.1457 0.0500 Uiso
H(18) 1.0000 0.1430 -0.2410 0.2402 0.0500 Uiso
H(19) 1.0000 0.0893 -0.3012 0.4069 0.0500 Uiso
H(20) 1.0000 0.0517 -0.1345 0.5309 0.0500 Uiso
H(21) 1.0000 0.0679 0.0926 0.4881 0.0500 Uiso
H(22) 1.0000 0.1216 0.1528 0.3214 0.0500 Uiso
H(24) 1.0000 0.0553 0.1098 0.0721 0.0500 Uiso
H(25) 1.0000 -0.0105 0.1460 -0.0937 0.0500 Uiso
H(26) 1.0000 0.0205 0.1214 -0.2916 0.0500 Uiso
H(27) 1.0000 0.1173 0.0607 -0.3237 0.0500 Uiso
H(28) 1.0000 0.1831 0.0246 -0.1579 0.0500 Uiso
H(30) 1.0000 0.2021 0.2986 0.0098 0.0500 Uiso
H(31) 1.0000 0.2514 0.4980 0.0616 0.0500 Uiso
H(32) 1.0000 0.3059 0.5138 0.2462 0.0500 Uiso
H(33) 1.0000 0.3110 0.3302 0.3790 0.0500 Uiso
H(34) 1.0000 0.2616 0.1308 0.3272 0.0500 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
Sn -0.8730 1.4240
C 0.0020 0.0020
H 0.0000 0.0000
N 0.0040 0.0030
O 0.0080 0.0060
Cl 0.1320 0.1590
S 0.1100 0.1240
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-15 2 2
7 1 -7
11 2 4
-9 0 6
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
C(2) Sn(1) C(17) 109.2(2) yes
C(2) Sn(1) C(23) 107.9(2) yes
C(17) Sn(1) C(23) 109.50(10) yes
C(2) Sn(1) C(29) 115.5(2) yes
C(17) Sn(1) C(29) 107.20(10) yes
C(23) Sn(1) C(29) 107.30(10) yes
C(4) S(5) C(6) 105.3(2) yes
O(9) N(8) O(10) 120.3(5) yes
O(9) N(8) C(7) 121.1(5) yes
O(10) N(8) C(7) 118.6(4) yes
Sn(1) C(2) C(3) 116.5(4) yes
C(2) C(3) C(4) 114.5(4) yes
S(5) C(4) C(3) 105.6(4) yes
S(5) C(4) C(15) 108.9(4) yes
C(3) C(4) C(15) 114.3(5) yes
S(5) C(6) C(7) 119.8(2) yes
S(5) C(6) C(14) 120.2(2) yes
C(7) C(6) C(14) 120.00 no
N(8) C(7) C(6) 124.0(3) yes
N(8) C(7) C(11) 115.9(3) yes
C(6) C(7) C(11) 120.00 no
C(7) C(11) C(12) 120.00 no
C(11) C(12) C(13) 120.00 no
C(12) C(13) C(14) 120.00 no
C(6) C(14) C(13) 120.00 no
Cl(16) C(15) C(4) 112.4(4) yes
Sn(1) C(17) C(18) 121.3(2) yes
Sn(1) C(17) C(22) 118.7(2) yes
C(18) C(17) C(22) 120.00 no
C(17) C(18) C(19) 120.00 no
C(18) C(19) C(20) 120.00 no
C(19) C(20) C(21) 120.00 no
C(20) C(21) C(22) 120.00 no
C(17) C(22) C(21) 120.00 no
Sn(1) C(23) C(24) 121.1(2) yes
Sn(1) C(23) C(28) 118.8(2) yes
C(24) C(23) C(28) 120.00 no
C(23) C(24) C(25) 120.00 no
C(24) C(25) C(26) 120.00 no
C(25) C(26) C(27) 120.00 no
C(26) C(27) C(28) 120.00 no
C(23) C(28) C(27) 120.00 no
Sn(1) C(29) C(30) 119.7(2) yes
Sn(1) C(29) C(34) 120.3(2) yes
C(30) C(29) C(34) 120.00 no
C(29) C(30) C(31) 120.00 no
C(30) C(31) C(32) 120.00 no
C(31) C(32) C(33) 120.00 no
C(32) C(33) C(34) 120.00 no
C(29) C(34) C(33) 120.00 no
C(4) S(5) O(10) 177.5(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn(1) C(2) 2.162(5) yes
Sn(1) C(17) 2.146(2) yes
Sn(1) C(23) 2.140(2) yes
Sn(1) C(29) 2.147(2) yes
Cl(16) C(15) 1.799(7) yes
S(5) C(4) 1.811(5) yes
S(5) C(6) 1.782(2) yes
O(9) N(8) 1.196(6) yes
O(10) N(8) 1.173(6) yes
N(8) C(7) 1.404(5) yes
C(2) C(3) 1.498(9) yes
C(3) C(4) 1.543(7) yes
C(4) C(15) 1.497(8) yes
C(6) C(7) 1.39 no
C(6) C(14) 1.39 no
C(7) C(11) 1.39 no
C(11) C(12) 1.39 no
C(12) C(13) 1.39 no
C(13) C(14) 1.39 no
C(17) C(18) 1.39 no
C(17) C(22) 1.39 no
C(18) C(19) 1.39 no
C(19) C(20) 1.39 no
C(20) C(21) 1.39 no
C(21) C(22) 1.39 no
C(23) C(24) 1.39 no
C(23) C(28) 1.39 no
C(24) C(25) 1.39 no
C(25) C(26) 1.39 no
C(26) C(27) 1.39 no
C(27) C(28) 1.39 no
C(29) C(30) 1.39 no
C(29) C(34) 1.39 no
C(30) C(31) 1.39 no
C(31) C(32) 1.39 no
C(32) C(33) 1.39 no
C(33) C(34) 1.39 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
S5 O10 2.610(5) yes
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_publ_flag
Cl(16) C(15) C(4) S(5) 175.5(3) yes
O(10) N(8) C(7) C(6) 3.6(7) yes
