#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216014.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_2216014
loop_
_publ_author_name
'Ibis, Cemil'
'Deniz, N. Gulsah'
_publ_section_title
;
 1,1,2-Trichloro-4,4-bis(4-methylphenylsulfanyl)-3-nitrobuta-1,3-diene
;
_journal_coeditor_code           IM2039
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4394
_journal_page_last               o4394
_journal_paper_doi               10.1107/S1600536807050957
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H14 Cl3 N O2 S2'
_chemical_formula_moiety         'C18 H14 Cl3 N O2 S2'
_chemical_formula_sum            'C18 H14 Cl3 N O2 S2'
_chemical_formula_weight         446.79
_chemical_melting_point          .392E-305
_chemical_name_systematic
;
1,1,2-Trichloro-4,4-bis(4-methylphenylsulfanyl)-3-nitrobuta-1,3-diene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 98.630(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8850(10)
_cell_length_b                   6.8246(6)
_cell_length_c                   21.313(2)
_cell_measurement_reflns_used    5659
_cell_measurement_temperature    293.5
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.9
_cell_volume                     1996.7(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9817
_diffrn_measured_fraction_theta_max 0.9817
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID S'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.086
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            69322
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             912.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.0260
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
14.9656    -4.4915    13.6461
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0490
_reflns_number_gt                3254
_reflns_number_total             3653
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            im2039.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2216014
_cod_database_fobs_code          2216014
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
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_occupancy
S S(1) 0.56841(7) 0.0359(2) 0.88785(4) 0.0565(3) Uani d 1.00
Cl Cl(1) 0.34904(7) -0.2935(2) 0.74876(5) 0.0720(3) Uani d 1.00
Cl Cl(2) 0.55665(8) -0.3657(2) 0.76900(5) 0.0700(3) Uani d 1.00
S S(2) 0.74902(7) 0.2064(2) 0.83810(4) 0.0595(3) Uani d 1.00
Cl Cl(3) 0.38832(8) 0.1596(2) 0.74025(7) 0.0830(4) Uani d 1.00
O O(1) 0.5776(2) 0.0536(5) 0.65928(12) 0.0732(9) Uani d 1.00
O O(2) 0.6947(2) 0.2191(5) 0.71320(13) 0.0775(10) Uani d 1.00
N N(1) 0.6211(2) 0.1190(5) 0.70970(10) 0.0564(10) Uani d 1.00
C C(10) 0.6222(3) 0.1431(6) 1.0105(2) 0.0556(11) Uani d 1.00
C C(5) 0.6007(3) 0.2113(6) 0.9486(2) 0.0502(10) Uani d 1.00
C C(3) 0.5809(3) 0.0756(5) 0.7665(2) 0.0487(10) Uani d 1.00
C C(2) 0.4828(2) -0.0080(6) 0.7558(2) 0.0508(10) Uani d 1.00
C C(7) 0.6249(3) 0.5388(6) 0.9868(2) 0.0621(12) Uani d 1.00
C C(4) 0.6323(2) 0.1088(5) 0.8259(2) 0.0473(10) Uani d 1.00
C C(6) 0.6005(3) 0.4103(6) 0.9371(2) 0.0590(11) Uani d 1.00
C C(12) 0.7987(3) 0.1309(6) 0.9161(2) 0.0539(11) Uani d 1.00
C C(13) 0.8408(3) 0.2735(7) 0.9576(2) 0.0615(12) Uani d 1.00
C C(14) 0.8875(3) 0.2180(8) 1.0170(2) 0.0682(13) Uani d 1.00
C C(8) 0.6484(3) 0.4734(6) 1.0485(2) 0.0594(12) Uani d 1.00
C C(1) 0.4645(3) -0.1987(6) 0.7574(2) 0.0526(11) Uani d 1.00
C C(15) 0.8917(3) 0.0225(8) 1.0359(2) 0.0663(13) Uani d 1.00
C C(16) 0.8512(3) -0.1173(7) 0.9926(2) 0.0677(13) Uani d 1.00
C C(9) 0.6447(3) 0.2746(6) 1.0595(2) 0.0604(12) Uani d 1.00
C C(17) 0.8053(3) -0.0643(7) 0.9327(2) 0.0602(12) Uani d 1.00
C C(11) 0.6771(4) 0.6177(8) 1.1021(2) 0.082 Uani d 1.00
C C(18) 0.9416(4) -0.0351(9) 1.1015(2) 0.091 Uani d 1.00
H H(1) 0.5825(3) 0.4578(6) 0.8951(2) 0.071 Uiso d 1.00
H H(2) 0.6258(3) 0.6758(6) 0.9791(2) 0.075 Uiso d 1.00
H H(3) 0.6583(3) 0.2279(6) 1.1018(2) 0.073 Uiso d 1.00
H H(4) 0.6200(3) 0.0062(6) 1.0182(2) 0.068 Uiso d 1.00
H H(5) 0.6919(4) 0.5500(8) 1.1413(2) 0.099 Uiso d 1.00
H H(6) 0.7323(4) 0.6911(8) 1.0944(2) 0.099 Uiso d 1.00
H H(7) 0.6239(4) 0.7038(8) 1.1038(2) 0.099 Uiso d 1.00
H H(8) 0.8383(3) 0.4066(7) 0.9444(2) 0.074 Uiso d 1.00
H H(9) 0.9154(3) 0.3151(8) 1.0461(2) 0.082 Uiso d 1.00
H H(10) 0.8549(3) -0.2514(7) 1.0047(2) 0.082 Uiso d 1.00
H H(11) 0.7786(3) -0.1610(7) 0.9030(2) 0.072 Uiso d 1.00
H H(12) 0.9391(4) -0.1731(9) 1.1068(2) 0.109 Uiso d 1.00
H H(13) 1.0077(4) 0.0061(9) 1.1063(2) 0.109 Uiso d 1.00
H H(14) 0.9099(4) 0.0275(9) 1.1326(2) 0.109 Uiso d 1.00
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, 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
C(5) S(1) C(4) 104.8(2)
C(4) S(2) C(12) 104.6(2)
C(3) N(1) O(1) 117.2(3)
C(3) N(1) O(2) 119.4(3)
O(1) N(1) O(2) 123.4(3)
C(5) C(10) C(9) 119.6(4)
C(5) C(10) H(4) 119.2(4)
C(9) C(10) H(4) 121.2(4)
C(6) C(5) S(1) 122.7(3)
C(6) C(5) C(10) 119.6(3)
S(1) C(5) C(10) 117.6(3)
C(2) C(3) C(4) 123.3(3)
C(2) C(3) N(1) 114.8(3)
C(4) C(3) N(1) 121.8(3)
C(1) C(2) Cl(3) 120.6(3)
C(1) C(2) C(3) 123.8(3)
Cl(3) C(2) C(3) 115.6(3)
C(6) C(7) C(8) 121.5(4)
C(6) C(7) H(2) 120.1(4)
C(8) C(7) H(2) 118.4(4)
S(1) C(4) S(2) 123.9(2)
S(1) C(4) C(3) 113.1(3)
S(2) C(4) C(3) 123.0(3)
H(1) C(6) C(5) 119.8(4)
H(1) C(6) C(7) 120.5(5)
C(5) C(6) C(7) 119.7(3)
C(13) C(12) C(17) 120.7(3)
C(13) C(12) S(2) 117.5(3)
C(17) C(12) S(2) 121.4(3)
C(14) C(13) H(8) 121.5(5)
C(14) C(13) C(12) 119.1(4)
H(8) C(13) C(12) 119.4(4)
C(15) C(14) H(9) 119.0(5)
C(15) C(14) C(13) 121.3(4)
H(9) C(14) C(13) 119.7(6)
C(9) C(8) C(11) 121.6(3)
C(9) C(8) C(7) 118.1(3)
C(11) C(8) C(7) 120.4(4)
Cl(1) C(1) Cl(2) 115.7(2)
Cl(1) C(1) C(2) 123.2(3)
Cl(2) C(1) C(2) 121.1(3)
C(16) C(15) C(18) 121.3(5)
C(16) C(15) C(14) 118.2(4)
C(18) C(15) C(14) 120.6(4)
C(17) C(16) H(10) 119.9(5)
C(17) C(16) C(15) 121.2(4)
H(10) C(16) C(15) 118.9(5)
H(3) C(9) C(10) 119.5(5)
H(3) C(9) C(8) 119.0(5)
C(10) C(9) C(8) 121.5(3)
H(11) C(17) C(12) 119.8(4)
H(11) C(17) C(16) 120.8(5)
C(12) C(17) C(16) 119.5(4)
H(5) C(11) H(6) 109.5(6)
H(5) C(11) H(7) 109.5(7)
H(5) C(11) C(8) 110.2(5)
H(6) C(11) H(7) 109.5(7)
H(6) C(11) C(8) 109.9(5)
H(7) C(11) C(8) 108.3(5)
H(12) C(18) H(13) 109.5(7)
H(12) C(18) H(14) 109.5(7)
H(12) C(18) C(15) 110.3(5)
H(13) C(18) H(14) 109.5(7)
H(13) C(18) C(15) 108.8(5)
H(14) C(18) C(15) 109.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S(1) C(5) 1.771(4)
S(1) C(4) 1.768(4)
Cl(1) C(1) 1.713(4)
Cl(2) C(1) 1.703(4)
S(2) C(4) 1.736(3)
S(2) C(12) 1.779(4)
Cl(3) C(2) 1.734(4)
O(1) N(1) 1.235(4)
O(2) N(1) 1.221(5)
N(1) C(3) 1.437(5)
C(10) C(5) 1.387(5)
C(10) C(9) 1.377(5)
C(10) H(4) 0.950(6)
C(5) C(6) 1.380(6)
C(3) C(2) 1.462(5)
C(3) C(4) 1.377(5)
C(2) C(1) 1.328(6)
C(7) C(6) 1.379(5)
C(7) C(8) 1.379(5)
C(7) H(2) 0.950(6)
C(6) H(1) 0.950(5)
C(12) C(13) 1.384(6)
C(12) C(17) 1.377(6)
C(13) C(14) 1.386(5)
C(13) H(8) 0.950(6)
C(14) C(15) 1.392(7)
C(14) H(9) 0.950(6)
C(8) C(9) 1.379(6)
C(8) C(11) 1.516(6)
C(15) C(16) 1.387(6)
C(15) C(18) 1.517(6)
C(16) C(17) 1.387(5)
C(16) H(10) 0.950(7)
C(9) H(3) 0.950(5)
C(17) H(11) 0.950(6)
C(11) H(5) 0.950(7)
C(11) H(6) 0.950(8)
C(11) H(7) 0.950(8)
C(18) H(12) 0.950(9)
C(18) H(13) 0.950(7)
C(18) H(14) 0.950(7)
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
C(4) S(1) C(5) C(10) -136.8(3)
C(4) S(1) C(5) C(6) 46.5(3)
C(5) S(1) C(4) S(2) 37.1(3)
C(5) S(1) C(4) C(3) -144.4(3)
C(12) S(2) C(4) S(1) 20.6(3)
C(12) S(2) C(4) C(3) -157.7(3)
C(4) S(2) C(12) C(13) -129.4(3)
C(4) S(2) C(12) C(17) 57.9(3)
O(1) N(1) C(3) C(2) -11.5(5)
O(1) N(1) C(3) C(4) 167.6(4)
O(2) N(1) C(3) C(2) 167.5(3)
O(2) N(1) C(3) C(4) -13.4(6)
C(9) C(10) C(5) S(1) -178.0(3)
C(9) C(10) C(5) C(6) -1.1(6)
H(4) C(10) C(5) S(1) 0.9(6)
H(4) C(10) C(5) C(6) 177.8(5)
C(5) C(10) C(9) C(8) -1.4(6)
C(5) C(10) C(9) H(3) 178.8(5)
H(4) C(10) C(9) C(8) 179.7(5)
H(4) C(10) C(9) H(3) 0.0(8)
S(1) C(5) C(6) C(7) 178.9(3)
S(1) C(5) C(6) H(1) -0.1(7)
C(10) C(5) C(6) C(7) 2.2(6)
C(10) C(5) C(6) H(1) -176.8(5)
N(1) C(3) C(2) Cl(3) -83.0(4)
N(1) C(3) C(2) C(1) 96.9(4)
C(4) C(3) C(2) Cl(3) 97.8(4)
C(4) C(3) C(2) C(1) -82.2(5)
N(1) C(3) C(4) S(1) -178.0(3)
N(1) C(3) C(4) S(2) 0.4(5)
C(2) C(3) C(4) S(1) 1.1(5)
C(2) C(3) C(4) S(2) 179.5(3)
Cl(3) C(2) C(1) Cl(1) -3.4(4)
Cl(3) C(2) C(1) Cl(2) 177.0(2)
C(3) C(2) C(1) Cl(1) 176.6(3)
C(3) C(2) C(1) Cl(2) -3.0(5)
C(8) C(7) C(6) C(5) -1.0(6)
C(8) C(7) C(6) H(1) 178.0(5)
H(2) C(7) C(6) C(5) 179.1(5)
H(2) C(7) C(6) H(1) -1.9(8)
C(6) C(7) C(8) C(9) -1.4(6)
C(6) C(7) C(8) C(11) 178.7(4)
H(2) C(7) C(8) C(9) 178.5(5)
H(2) C(7) C(8) C(11) -1.4(7)
S(2) C(12) C(13) C(14) -174.7(3)
S(2) C(12) C(13) H(8) 4.0(6)
C(17) C(12) C(13) C(14) -1.8(6)
C(17) C(12) C(13) H(8) 176.8(5)
S(2) C(12) C(17) C(16) 175.2(3)
S(2) C(12) C(17) H(11) -4.6(6)
C(13) C(12) C(17) C(16) 2.6(6)
C(13) C(12) C(17) H(11) -177.2(5)
C(12) C(13) C(14) C(15) -0.8(6)
C(12) C(13) C(14) H(9) -178.8(5)
H(8) C(13) C(14) C(15) -179.4(5)
H(8) C(13) C(14) H(9) 2.6(8)
C(13) C(14) C(15) C(16) 2.5(6)
C(13) C(14) C(15) C(18) -179.0(4)
H(9) C(14) C(15) C(16) -179.5(5)
H(9) C(14) C(15) C(18) -1.0(7)
C(7) C(8) C(9) C(10) 2.6(6)
C(7) C(8) C(9) H(3) -177.6(5)
C(11) C(8) C(9) C(10) -177.5(4)
C(11) C(8) C(9) H(3) 2.3(7)
C(7) C(8) C(11) H(5) -179.2(6)
C(7) C(8) C(11) H(6) -58.4(7)
C(7) C(8) C(11) H(7) 61.1(7)
C(9) C(8) C(11) H(5) 1.0(8)
C(9) C(8) C(11) H(6) 121.7(6)
C(9) C(8) C(11) H(7) -118.8(6)
C(14) C(15) C(16) C(17) -1.7(6)
C(14) C(15) C(16) H(10) 178.7(5)
C(18) C(15) C(16) C(17) 179.8(4)
C(18) C(15) C(16) H(10) 0.2(7)
C(14) C(15) C(18) H(12) -179.2(5)
C(14) C(15) C(18) H(13) -59.1(7)
C(14) C(15) C(18) H(14) 60.4(7)
C(16) C(15) C(18) H(12) -0.8(7)
C(16) C(15) C(18) H(13) 119.4(7)
C(16) C(15) C(18) H(14) -121.2(6)
C(15) C(16) C(17) C(12) -0.8(6)
C(15) C(16) C(17) H(11) 179.0(5)
H(10) C(16) C(17) C(12) 178.8(5)
H(10) C(16) C(17) H(11) -1.5(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21121240
