#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/44/2214443.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_2214443
loop_
_publ_author_name
'Ibis, Cemil'
'Deniz, N.Gulsah'
_publ_section_title
1,1-Dichloro-3-(6,1,3-oxadithiaoctocan-2-ylidene)-3-nitro-2-(4-methylphenylsulfanyl)propene
_journal_coeditor_code           XU2259
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3058
_journal_page_last               o3058
_journal_paper_doi               10.1107/S1600536807025731
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H15 Cl2 N O3 S3'
_chemical_formula_moiety         'C15 H15 Cl2 N O3 S3'
_chemical_formula_sum            'C15 H15 Cl2 N O3 S3'
_chemical_formula_weight         424.37
_chemical_melting_point          419.0(10)
_chemical_name_systematic
;
1,1-Dichloro-3-(6,1,3-oxadithiaoctocan-2-ylidene)-3-nitro-
2-(4-methylphenylsulfanyl)propene
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5112(5)
_cell_length_b                   18.0213(6)
_cell_length_c                   7.5559(2)
_cell_measurement_reflns_used    10401
_cell_measurement_temperature    293.5
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     1839.78(10)
_computing_cell_refinement       CrystalClear
_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
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.034
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            69828
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 11 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.0110
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin (1979).
Acta Cryst. A35, 698--699)
   4.7778    -2.5240    3.7682
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.027
_reflns_number_gt                1886
_reflns_number_total             1897
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            xu2259.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '418-420' was changed to '419.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '418-420' was changed to '419.0(10)'
- 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_database_code               2214443
_cod_database_fobs_code          2214443
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,-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_occupancy
S S(2) 0.91725(5) 0.26150(4) 1.20586(11) 0.0540(2) Uani d 1.00
S S(1) 0.84229(6) 0.44795(4) 1.09641(10) 0.0555(2) Uani d 1.00
S S(3) 0.82153(6) 0.16803(4) 0.91382(11) 0.0616(2) Uani d 1.00
Cl Cl(1) 0.67918(7) 0.45722(5) 1.38723(12) 0.0775(3) Uani d 1.00
Cl Cl(2) 0.60463(6) 0.31134(5) 1.29690(10) 0.0780(3) Uani d 1.00
O O(3) 0.8220(2) 0.09720(12) 1.2966(3) 0.0685(6) Uani d 1.00
O O(2) 0.6445(2) 0.36598(12) 0.8510(3) 0.0680(7) Uani d 1.00
N N(1) 0.6947(2) 0.30988(13) 0.8709(3) 0.0550(7) Uani d 1.00
C C(12) 1.0330(2) 0.38950(10) 0.6181(4) 0.0504(8) Uani d 1.00
O O(1) 0.6907(2) 0.25714(13) 0.7694(3) 0.0866(8) Uani d 1.00
C C(2) 0.7595(2) 0.37355(13) 1.1325(4) 0.0452(7) Uani d 1.00
C C(9) 0.9120(2) 0.41788(13) 0.9113(4) 0.0468(7) Uani d 1.00
C C(11) 1.0693(2) 0.3824(2) 0.7885(4) 0.0561(8) Uani d 1.00
C C(3) 0.7635(2) 0.30660(10) 1.0190(4) 0.0446(7) Uani d 1.00
C C(4) 0.8237(2) 0.24795(13) 1.0448(3) 0.0435(7) Uani d 1.00
C C(14) 0.8750(2) 0.4239(2) 0.7403(4) 0.0538(8) Uani d 1.00
C C(13) 0.9349(2) 0.4091(2) 0.5970(4) 0.0566(8) Uani d 1.00
C C(10) 1.0099(2) 0.3963(2) 0.9345(4) 0.0530(8) Uani d 1.00
C C(1) 0.6910(2) 0.3792(2) 1.2578(4) 0.0540(8) Uani d 1.00
C C(6) 0.8883(3) 0.1338(2) 1.4124(5) 0.0684(10) Uani d 1.00
C C(5) 0.8718(3) 0.2166(2) 1.4040(4) 0.0645(9) Uani d 1.00
C C(7) 0.8667(3) 0.0581(2) 1.1558(5) 0.0684(10) Uani d 1.00
C C(8) 0.9115(2) 0.1069(2) 1.0145(5) 0.0623(9) Uani d 1.00
C C(15) 1.0992(3) 0.3795(2) 0.4603(4) 0.0729(10) Uani d 1.00
H H(1) 0.8085(2) 0.4397(2) 0.7242(4) 0.0645 Uiso d 1.00
H H(2) 0.9074(2) 0.4117(2) 0.4815(4) 0.0680 Uiso d 1.00
H H(3) 1.1367(2) 0.3693(2) 0.8068(4) 0.0672 Uiso d 1.00
H H(4) 1.0358(2) 0.3910(2) 1.0507(4) 0.0636 Uiso d 1.00
H H(5) 0.9025(3) 0.2397(2) 1.5029(4) 0.077 Uiso d 1.00
H H(6) 0.8022(3) 0.2238(2) 1.4104(4) 0.077 Uiso d 1.00
H H(7) 0.8786(3) 0.1156(2) 1.5291(5) 0.082 Uiso d 1.00
H H(8) 0.9545(3) 0.1244(2) 1.3765(5) 0.082 Uiso d 1.00
H H(9) 0.9401(2) 0.0766(2) 0.9254(5) 0.075 Uiso d 1.00
H H(10) 0.9615(2) 0.1364(2) 1.0679(5) 0.075 Uiso d 1.00
H H(11) 0.9164(3) 0.0264(2) 1.2026(5) 0.082 Uiso d 1.00
H H(12) 0.8166(3) 0.0290(2) 1.1010(5) 0.082 Uiso d 1.00
H H(13) 1.1272(3) 0.3312(2) 0.4628(4) 0.088 Uiso d 1.00
H H(14) 1.0614(3) 0.3854(2) 0.3551(4) 0.088 Uiso d 1.00
H H(15) 1.1506(3) 0.4155(2) 0.4628(4) 0.088 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
_geom_angle_publ_flag
C(4) S(2) C(5) 105.40(10) ?
C(2) S(1) C(9) 103.10(10) ?
C(4) S(3) C(8) 104.60(10) ?
C(6) O(3) C(7) 115.4(2) ?
O(1) N(1) C(3) 118.6(2) ?
O(1) N(1) O(2) 122.6(3) ?
C(3) N(1) O(2) 118.8(2) ?
C(11) C(12) C(13) 118.1(3) ?
C(11) C(12) C(15) 121.1(3) ?
C(13) C(12) C(15) 120.7(3) ?
C(3) C(2) C(1) 120.1(2) yes
C(3) C(2) S(1) 120.4(2) ?
C(1) C(2) S(1) 119.5(2) ?
C(14) C(9) C(10) 118.8(3) ?
C(14) C(9) S(1) 121.3(2) ?
C(10) C(9) S(1) 119.5(2) ?
C(10) C(11) H(3) 118.9(4) ?
C(10) C(11) C(12) 121.1(3) ?
H(3) C(11) C(12) 119.9(4) ?
C(4) C(3) N(1) 121.9(2) ?
C(4) C(3) C(2) 125.2(2) yes
N(1) C(3) C(2) 112.9(2) ?
S(2) C(4) S(3) 121.00(10) ?
S(2) C(4) C(3) 115.0(2) ?
S(3) C(4) C(3) 123.6(2) ?
C(13) C(14) H(1) 120.8(3) ?
C(13) C(14) C(9) 120.3(3) ?
H(1) C(14) C(9) 118.8(3) ?
H(2) C(13) C(12) 119.6(3) ?
H(2) C(13) C(14) 118.9(3) ?
C(12) C(13) C(14) 121.5(3) ?
H(4) C(10) C(9) 119.7(3) ?
H(4) C(10) C(11) 120.2(4) ?
C(9) C(10) C(11) 120.1(3) ?
Cl(1) C(1) Cl(2) 114.9(2) ?
Cl(1) C(1) C(2) 122.2(2) ?
Cl(2) C(1) C(2) 122.8(2) ?
C(5) C(6) H(7) 111.1(4) ?
C(5) C(6) H(8) 107.6(4) ?
C(5) C(6) O(3) 110.0(3) ?
H(7) C(6) H(8) 109.5(5) ?
H(7) C(6) O(3) 109.0(4) ?
H(8) C(6) O(3) 109.7(4) ?
H(5) C(5) H(6) 109.5(4) ?
H(5) C(5) S(2) 107.9(3) ?
H(5) C(5) C(6) 109.6(3) ?
H(6) C(5) S(2) 108.5(3) ?
H(6) C(5) C(6) 106.1(3) ?
S(2) C(5) C(6) 115.2(2) ?
C(8) C(7) H(11) 109.3(4) ?
C(8) C(7) H(12) 107.4(4) ?
C(8) C(7) O(3) 114.4(2) ?
H(11) C(7) H(12) 109.5(4) ?
H(11) C(7) O(3) 108.8(4) ?
H(12) C(7) O(3) 107.4(4) ?
H(9) C(8) H(10) 109.5(4) ?
H(9) C(8) S(3) 109.0(3) ?
H(9) C(8) C(7) 109.2(3) ?
H(10) C(8) S(3) 108.4(3) ?
H(10) C(8) C(7) 108.1(4) ?
S(3) C(8) C(7) 112.5(2) ?
H(13) C(15) H(14) 109.5(5) ?
H(13) C(15) H(15) 109.5(5) ?
H(13) C(15) C(12) 109.3(4) ?
H(14) C(15) H(15) 109.5(5) ?
H(14) C(15) C(12) 109.3(4) ?
H(15) C(15) C(12) 109.7(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(2) C(4) 1.771(3) ?
S(2) C(5) 1.809(3) ?
S(1) C(2) 1.767(3) ?
S(1) C(9) 1.771(3) ?
S(3) C(4) 1.748(2) ?
S(3) C(8) 1.808(3) ?
Cl(1) C(1) 1.720(3) ?
Cl(2) C(1) 1.716(3) ?
O(3) C(6) 1.415(4) ?
O(3) C(7) 1.412(4) ?
O(2) N(1) 1.227(3) ?
N(1) O(1) 1.222(3) ?
N(1) C(3) 1.455(4) ?
C(12) C(11) 1.384(4) ?
C(12) C(13) 1.381(4) ?
C(12) C(15) 1.501(5) ?
C(2) C(3) 1.481(4) yes
C(2) C(1) 1.328(4) yes
C(9) C(14) 1.389(4) ?
C(9) C(10) 1.390(4) ?
C(11) C(10) 1.387(4) ?
C(11) H(3) 0.950(4) ?
C(3) C(4) 1.348(4) yes
C(14) C(13) 1.377(4) ?
C(14) H(1) 0.950(4) ?
C(13) H(2) 0.950(4) ?
C(10) H(4) 0.950(4) ?
C(6) C(5) 1.510(4) ?
C(6) H(7) 0.950(5) ?
C(6) H(8) 0.950(5) ?
C(5) H(5) 0.950(5) ?
C(5) H(6) 0.950(5) ?
C(7) C(8) 1.510(5) ?
C(7) H(11) 0.950(5) ?
C(7) H(12) 0.950(5) ?
C(8) H(9) 0.950(5) ?
C(8) H(10) 0.950(4) ?
C(15) H(13) 0.950(5) ?
C(15) H(14) 0.950(5) ?
C(15) H(15) 0.950(5) ?
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
C(5) S(2) C(4) S(3) -87.1(2) ?
C(5) S(2) C(4) C(3) 100.1(2) ?
C(4) S(2) C(5) C(6) 82.4(3) ?
C(4) S(2) C(5) H(5) -154.9(3) ?
C(4) S(2) C(5) H(6) -36.4(3) ?
C(9) S(1) C(2) C(3) 1.2(2) ?
C(9) S(1) C(2) C(1) -176.2(2) ?
C(2) S(1) C(9) C(14) 80.2(2) ?
C(2) S(1) C(9) C(10) -107.8(2) ?
C(8) S(3) C(4) S(2) 10.9(2) ?
C(8) S(3) C(4) C(3) -176.9(2) ?
C(4) S(3) C(8) C(7) 89.4(2) ?
C(4) S(3) C(8) H(9) -149.3(3) ?
C(4) S(3) C(8) H(10) -30.2(4) ?
C(7) O(3) C(6) C(5) 116.5(3) ?
C(7) O(3) C(6) H(7) -121.5(4) ?
C(7) O(3) C(6) H(8) -1.7(4) ?
C(6) O(3) C(7) C(8) -71.2(3) ?
C(6) O(3) C(7) H(11) 51.4(4) ?
C(6) O(3) C(7) H(12) 169.7(3) ?
O(2) N(1) C(3) C(2) 2.2(4) ?
O(2) N(1) C(3) C(4) -177.3(3) ?
O(1) N(1) C(3) C(2) -179.1(2) ?
O(1) N(1) C(3) C(4) 1.3(4) ?
C(13) C(12) C(11) C(10) -1.7(4) ?
C(13) C(12) C(11) H(3) -179.6(3) ?
C(15) C(12) C(11) C(10) 175.8(3) ?
C(15) C(12) C(11) H(3) -2.1(5) ?
C(11) C(12) C(13) C(14) 2.3(4) ?
C(11) C(12) C(13) H(2) -176.6(3) ?
C(15) C(12) C(13) C(14) -175.1(3) ?
C(15) C(12) C(13) H(2) 6.0(5) ?
C(11) C(12) C(15) H(13) 58.9(5) ?
C(11) C(12) C(15) H(14) 178.8(4) ?
C(11) C(12) C(15) H(15) -61.1(5) ?
C(13) C(12) C(15) H(13) -123.7(4) ?
C(13) C(12) C(15) H(14) -3.9(5) ?
C(13) C(12) C(15) H(15) 116.2(4) ?
S(1) C(2) C(3) N(1) -94.2(3) ?
S(1) C(2) C(3) C(4) 85.4(3) ?
C(1) C(2) C(3) N(1) 83.2(3) ?
C(1) C(2) C(3) C(4) -97.2(3) yes
S(1) C(2) C(1) Cl(1) 0.3(4) ?
S(1) C(2) C(1) Cl(2) 177.5(2) ?
C(3) C(2) C(1) Cl(1) -177.1(2) ?
C(3) C(2) C(1) Cl(2) 0.1(4) ?
S(1) C(9) C(14) C(13) 171.7(2) ?
S(1) C(9) C(14) H(1) -6.6(4) ?
C(10) C(9) C(14) C(13) -0.3(4) ?
C(10) C(9) C(14) H(1) -178.6(3) ?
S(1) C(9) C(10) C(11) -171.2(2) ?
S(1) C(9) C(10) H(4) 9.1(4) ?
C(14) C(9) C(10) C(11) 1.0(4) ?
C(14) C(9) C(10) H(4) -178.7(3) ?
C(12) C(11) C(10) C(9) 0.0(4) ?
C(12) C(11) C(10) H(4) 179.7(3) ?
H(3) C(11) C(10) C(9) 177.9(3) ?
H(3) C(11) C(10) H(4) -2.3(5) ?
N(1) C(3) C(4) S(2) 168.8(2) ?
N(1) C(3) C(4) S(3) -3.8(4) ?
C(2) C(3) C(4) S(2) -10.8(4) ?
C(2) C(3) C(4) S(3) 176.7(2) ?
C(9) C(14) C(13) C(12) -1.4(4) ?
C(9) C(14) C(13) H(2) 177.6(3) ?
H(1) C(14) C(13) C(12) 176.9(3) ?
H(1) C(14) C(13) H(2) -4.2(5) ?
O(3) C(6) C(5) S(2) -74.0(4) yes
O(3) C(6) C(5) H(5) 164.1(4) ?
O(3) C(6) C(5) H(6) 46.1(4) ?
H(7) C(6) C(5) S(2) 165.2(4) ?
H(7) C(6) C(5) H(5) 43.4(6) ?
H(7) C(6) C(5) H(6) -74.7(5) ?
H(8) C(6) C(5) S(2) 45.4(4) ?
H(8) C(6) C(5) H(5) -76.4(5) ?
H(8) C(6) C(5) H(6) 165.5(4) ?
O(3) C(7) C(8) S(3) -59.0(4) yes
O(3) C(7) C(8) H(9) 179.7(4) ?
O(3) C(7) C(8) H(10) 60.7(4) ?
H(11) C(7) C(8) S(3) 178.7(3) ?
H(11) C(7) C(8) H(9) 57.5(5) ?
H(11) C(7) C(8) H(10) -61.6(5) ?
H(12) C(7) C(8) S(3) 60.0(4) ?
H(12) C(7) C(8) H(9) -61.2(5) ?
H(12) C(7) C(8) H(10) 179.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124055
