#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/11/2201146.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_2201146
loop_
_publ_author_name
'Jones, Peter G.'
'Bubenitschek, Peter'
'Sander, Wolfram'
'Wierlacher, Stefan'
_publ_section_title
;
 trans-3,6-Bis(chlorophenylmethylene)-1,2,4,5-tetrathiane
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o555
_journal_page_last               o556
_journal_paper_doi               10.1107/S1600536802006372
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C16 H10 Cl2 S4'
_chemical_formula_moiety         'C16 H10 Cl2 S4'
_chemical_formula_sum            'C16 H10 Cl2 S4'
_chemical_formula_weight         401.38
_chemical_name_systematic
;
trans-3,6-Bis(chlorophenylmethylene)-1,2,4,5-tetrathiane
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c 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                   7.611(4)
_cell_length_b                   17.137(5)
_cell_length_c                   26.161(10)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      11.2
_cell_measurement_theta_min      10
_cell_volume                     3412(2)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Stoe STADI-4'
_diffrn_measurement_method       ω/θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2845
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.455
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0776P)²+7.2011P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                2414
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6154.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (12 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2201146
_cod_database_fobs_code          2201146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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
_atom_site_type_symbol
S1 0.60339(13) 0.48438(5) 0.34817(3) 0.0284(3) Uani d . 1 . . S
S2 0.46901(14) 0.64959(5) 0.34243(4) 0.0326(3) Uani d . 1 . . S
S3 0.76821(12) 0.54307(5) 0.39669(3) 0.0282(2) Uani d . 1 . . S
S4 0.40854(13) 0.61150(6) 0.41441(4) 0.0326(3) Uani d . 1 . . S
Cl1 0.42775(15) 0.64014(5) 0.22748(4) 0.0372(3) Uani d . 1 . . Cl
Cl2 0.87739(14) 0.58501(7) 0.50623(4) 0.0441(3) Uani d . 1 . . Cl
C1 0.5216(5) 0.5618(2) 0.31008(13) 0.0242(7) Uani d . 1 . . C
C2 0.6188(5) 0.5893(2) 0.43936(13) 0.0252(8) Uani d . 1 . . C
C3 0.5001(5) 0.5560(2) 0.25935(13) 0.0266(8) Uani d . 1 . . C
C4 0.6657(5) 0.6094(2) 0.48640(13) 0.0266(8) Uani d . 1 . . C
C5 0.5323(5) 0.4880(2) 0.22703(13) 0.0257(7) Uani d . 1 . . C
C6 0.4831(5) 0.4139(2) 0.24334(14) 0.0313(8) Uani d . 1 . . C
H6 0.4261 0.4075 0.2754 0.038 Uiso calc R 1 . . H
C7 0.5170(6) 0.3491(2) 0.21298(15) 0.0388(10) Uani d . 1 . . C
H7 0.4846 0.2986 0.2245 0.047 Uiso calc R 1 . . H
C8 0.5980(6) 0.3581(2) 0.16587(16) 0.0396(10) Uani d . 1 . . C
H8 0.6221 0.3137 0.1453 0.047 Uiso calc R 1 . . H
C9 0.6434(5) 0.4315(2) 0.14901(14) 0.0348(9) Uani d . 1 . . C
H9 0.6982 0.4376 0.1166 0.042 Uiso calc R 1 . . H
C10 0.6099(5) 0.4963(2) 0.17885(14) 0.0293(8) Uani d . 1 . . C
H10 0.6397 0.5468 0.1666 0.035 Uiso calc R 1 . . H
C11 0.5577(5) 0.6518(2) 0.52431(13) 0.0267(8) Uani d . 1 . . C
C12 0.3871(5) 0.6285(2) 0.53414(14) 0.0317(8) Uani d . 1 . . C
H12 0.3391 0.5849 0.5166 0.038 Uiso calc R 1 . . H
C13 0.2855(5) 0.6687(2) 0.56963(15) 0.0363(9) Uani d . 1 . . C
H13 0.1679 0.6528 0.5759 0.044 Uiso calc R 1 . . H
C14 0.3545(6) 0.7315(2) 0.59585(15) 0.0381(9) Uani d . 1 . . C
H14 0.2853 0.7585 0.6203 0.046 Uiso calc R 1 . . H
C15 0.5254(6) 0.7547(3) 0.58616(17) 0.0428(10) Uani d . 1 . . C
H15 0.5728 0.7983 0.6039 0.051 Uiso calc R 1 . . H
C16 0.6270(5) 0.7157(2) 0.55136(15) 0.0359(9) Uani d . 1 . . C
H16 0.7447 0.7318 0.5455 0.043 Uiso calc R 1 . . H
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'
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'
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
C1 S1 S3 101.30(10) y
C1 S2 S4 102.70(10) y
C2 S3 S1 102.50(10) y
C2 S4 S2 101.80(10) y
C3 C1 S1 123.0(3) ?
C3 C1 S2 120.5(3) ?
S1 C1 S2 116.5(2) y
C4 C2 S4 122.0(3) ?
C4 C2 S3 121.7(3) ?
S4 C2 S3 116.2(2) y
C1 C3 C5 127.7(3) y
C1 C3 Cl1 116.6(3) y
C5 C3 Cl1 115.7(3) y
C2 C4 C11 126.8(4) y
C2 C4 Cl2 117.6(3) y
C11 C4 Cl2 115.6(3) y
C6 C5 C10 118.8(3) ?
C6 C5 C3 120.4(3) ?
C10 C5 C3 120.8(3) ?
C7 C6 C5 120.3(4) ?
C7 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
C8 C7 C6 120.2(4) ?
C8 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
C9 C8 C7 119.9(4) ?
C9 C8 H8 120.1 ?
C7 C8 H8 120.1 ?
C8 C9 C10 120.5(4) ?
C8 C9 H9 119.8 ?
C10 C9 H9 119.8 ?
C9 C10 C5 120.4(3) ?
C9 C10 H10 119.8 ?
C5 C10 H10 119.8 ?
C12 C11 C16 118.9(3) ?
C12 C11 C4 120.3(3) ?
C16 C11 C4 120.8(3) ?
C11 C12 C13 120.2(4) ?
C11 C12 H12 119.9 ?
C13 C12 H12 119.9 ?
C14 C13 C12 120.4(4) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C13 C14 C15 119.4(4) ?
C13 C14 H14 120.3 ?
C15 C14 H14 120.3 ?
C16 C15 C14 120.8(4) ?
C16 C15 H15 119.6 ?
C14 C15 H15 119.6 ?
C15 C16 C11 120.2(4) ?
C15 C16 H16 119.9 ?
C11 C16 H16 119.9 ?
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
S1 C1 . 1.772(4) y
S1 S3 . 2.049(2) y
S2 C1 . 1.772(3) y
S2 S4 . 2.046(2) y
S3 C2 . 1.780(4) y
S4 C2 . 1.770(4) y
Cl1 C3 . 1.754(4) ?
Cl2 C4 . 1.743(4) ?
C1 C3 . 1.341(5) y
C2 C4 . 1.327(5) y
C3 C5 . 1.460(5) ?
C4 C11 . 1.479(5) ?
C5 C6 . 1.392(5) ?
C5 C10 . 1.399(5) ?
C6 C7 . 1.388(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.386(6) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.377(6) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.382(5) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.382(5) ?
C11 C16 . 1.406(5) ?
C12 C13 . 1.391(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.380(6) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.383(6) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.369(6) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8 S2 3_645 0.95 2.91 3.616(4) 132
C14 H14 S2 4_466 0.95 3.04 3.920(4) 155
C15 H15 S4 4_566 0.95 3.02 3.710(5) 130
C9 H9 Cl2 2_664 0.95 2.97 3.749(4) 140
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
C1 S1 S3 C2 75.0(2) y
C1 S2 S4 C2 74.5(2) y
S3 S1 C1 C3 138.6(3) ?
S3 S1 C1 S2 -41.0(2) y
S4 S2 C1 C3 153.0(3) ?
S4 S2 C1 S1 -27.4(2) y
S2 S4 C2 C4 136.5(3) ?
S2 S4 C2 S3 -40.3(2) y
S1 S3 C2 C4 155.1(3) ?
S1 S3 C2 S4 -28.2(2) y
S1 C1 C3 C5 2.0(6) ?
S2 C1 C3 C5 -178.3(3) ?
S1 C1 C3 Cl1 -177.0(2) ?
S2 C1 C3 Cl1 2.7(4) ?
S4 C2 C4 C11 -0.2(5) ?
S3 C2 C4 C11 176.3(3) ?
S4 C2 C4 Cl2 -179.3(2) ?
S3 C2 C4 Cl2 -2.8(4) ?
C1 C3 C5 C6 41.3(6) ?
Cl1 C3 C5 C6 -139.7(3) ?
C1 C3 C5 C10 -139.9(4) ?
Cl1 C3 C5 C10 39.1(4) ?
C10 C5 C6 C7 2.4(6) ?
C3 C5 C6 C7 -178.7(4) ?
C5 C6 C7 C8 -0.9(6) ?
C6 C7 C8 C9 -0.6(7) ?
C7 C8 C9 C10 0.4(6) ?
C8 C9 C10 C5 1.2(6) ?
C6 C5 C10 C9 -2.6(5) ?
C3 C5 C10 C9 178.6(3) ?
C2 C4 C11 C12 48.5(5) ?
Cl2 C4 C11 C12 -132.4(3) ?
C2 C4 C11 C16 -132.4(4) ?
Cl2 C4 C11 C16 46.8(4) ?
C16 C11 C12 C13 1.1(6) ?
C4 C11 C12 C13 -179.7(3) ?
C11 C12 C13 C14 -0.9(6) ?
C12 C13 C14 C15 0.7(6) ?
C13 C14 C15 C16 -0.7(7) ?
C14 C15 C16 C11 1.0(7) ?
C12 C11 C16 C15 -1.2(6) ?
C4 C11 C16 C15 179.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132365
