#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010264.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_2010264
loop_
_publ_author_name
'Swaminathan, K.'
'Carroll, Patrick J.'
'Singh, Jai D.'
'Singh, Harkesh B.'
_publ_section_title
;
 Bis(methylethylenedithio)tetrathiafulvalene
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1958
_journal_page_last               1960
_journal_paper_doi               10.1107/S0108270194004142
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C12 H12 S8'
_chemical_formula_sum            'C12 H12 S8'
_chemical_formula_weight         412.71
_chemical_name_systematic
;
Bis(methylethylenedithio)tetrathiafulvalene
;
_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                90.0
_cell_angle_beta                 97.260(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   6.5687(7)
_cell_length_b                   12.802(2)
_cell_length_c                   20.219(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      36.20
_cell_measurement_theta_min      15.47
_cell_volume                     1686.6(4)
_computing_molecular_graphics
'ORTEP (Johnson, 1976) and PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material  'SWATAB (Swaminathan, 1989)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELX86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'Copper K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3926
_diffrn_reflns_theta_max         72.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    9.269
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   'Empirical, \y-scan'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       Needle
_exptl_crystal_F_000             848.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.882
_refine_diff_density_min         0.784
_refine_ls_goodness_of_fit_obs   1.5576
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2914
_refine_ls_R_factor_obs          0.0738
_refine_ls_shift/esd_max         0.890
_refine_ls_shift/esd_mean        0.101
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         XX
_reflns_number_observed          3291
_reflns_number_total             3782
_reflns_observed_criterion       F>=3.0\s(F)
_cod_data_source_file            cr1087.cif
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_matrix_type' value 'Full' changed to 'full' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1686.65
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2010264
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
C(1) 0.4142(6) -0.0128(4) 0.1129(2) 0.049(3) Ueq ? ? C
C(2) 0.2581(8) -0.1314(6) 0.1949(3) 0.074(4) Ueq ? ? C
C(3) 0.1910(12) -0.2521(9) 0.3024(5) 0.145(5) Ueq ? ? C
C(4) 0.3695(13) -0.2348(11) 0.3266(5) 0.187(5) Ueq ? ? C
C(5) 0.4556(8) -0.1260(6) 0.2190(3) 0.071(4) Ueq ? ? C
C(6) 0.4359(6) 0.0664(4) 0.0709(2) 0.044(3) Ueq ? ? C
C(7) 0.3600(9) 0.2327(4) 0.0016(3) 0.058(4) Ueq ? ? C
C(8) 0.4234(13) 0.3627(8) -0.0979(4) 0.113(4) Ueq ? ? C
C(9) 0.6244(13) 0.3819(8) -0.0693(4) 0.122(5) Ueq ? ? C
C(10) 0.5600(8) 0.2385(4) 0.0254(3) 0.055(4) Ueq ? ? C
S(1) 0.1824(2) -0.07850(10) 0.11560(10) 0.0630(10) Ueq ? ? S
S(2) 0.0579(3) -0.1912(2) 0.23010(10) 0.130(3) Ueq ? ? S
S(3) 0.5800(3) -0.1793(2) 0.29270(10) 0.126(2) Ueq ? ? S
S(4) 0.6164(2) -0.06150(10) 0.16890(10) 0.0660(10) Ueq ? ? S
S(5) 0.2344(2) 0.11500(10) 0.01390(10) 0.0530(10) Ueq ? ? S
S(6) 0.2295(3) 0.32920(10) -0.04700(10) 0.080(2) Ueq ? ? S
S(7) 0.7215(3) 0.34240(10) 0.01380(10) 0.080(2) Ueq ? ? S
S(8) 0.6724(2) 0.12750(10) 0.06570(10) 0.0520(10) Ueq ? ? S
C(3M) 0.325(2) -0.3528(13) 0.2715(9) 0.177(5) Ueq ? ? C
C(4M) 0.237(2) -0.1386(15) 0.3540(9) 0.119(5) Ueq ? ? C
C(8M) 0.3435(15) 0.4196(9) -0.1553(5) 0.144(5) Ueq ? ? C
H(3) 0.0780 -0.2350 0.3360 0.050 Uiso ? ? H
H(31) 0.0957 -0.2882 0.3359 0.050 Uiso ? ? H
H(32) 0.1729 -0.2928 0.2555 0.050 Uiso ? ? H
H(3MA) 0.3758 -0.4023 0.3096 0.050 Uiso ? ? H
H(3MB) 0.4189 -0.3254 0.2404 0.050 Uiso ? ? H
H(3MC) 0.1900 -0.3978 0.2386 0.050 Uiso ? ? H
H(4) 0.5165 -0.2751 0.3356 0.050 Uiso ? ? H
H(41) 0.3662 -0.2009 0.3728 0.050 Uiso ? ? H
H(42) 0.4246 -0.3199 0.3354 0.050 Uiso ? ? H
H(4MA) 0.0980 -0.1435 0.3783 0.050 Uiso ? ? H
H(4MB) 0.2846 -0.0589 0.3524 0.050 Uiso ? ? H
H(4MC) 0.1738 -0.1571 0.2982 0.050 Uiso ? ? H
H(8) 0.4708 0.2829 -0.1203 0.050 Uiso ? ? H
H(8MA) 0.1863 0.3999 -0.1748 0.050 Uiso ? ? H
H(8MB) 0.4342 0.4283 -0.1946 0.050 Uiso ? ? H
H(8MC) 0.3255 0.5060 -0.1361 0.050 Uiso ? ? H
H(91) 0.7350 0.3528 -0.1009 0.050 Uiso ? ? H
H(92) 0.6363 0.4679 -0.0690 0.050 Uiso ? ? H
loop_
_atom_type_symbol
_atom_type_scat_source
C 'SHELX76 (Sheldrick, 1976)'
H 'SHELX76 (Sheldrick, 1976)'
S 'SHELX76 (Sheldrick, 1976)'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 4 0
1 3 -6
0 4 -3
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
S(1) C(1) C(6) 123.1(4) yes
S(4) C(1) C(6) 123.1(4) yes
S(4) C(1) S(1) 113.7(3) yes
S(1) C(2) C(5) 117.8(5) yes
S(2) C(2) C(5) 128.5(5) yes
S(2) C(2) S(1) 113.6(3) yes
S(2) C(3) C(4) 126.2(9) yes
C(3M) C(3) C(4) 77.1(9) yes
C(3M) C(3) S(2) 104.4(8) yes
C(4M) C(3) C(4) 62.6(9) yes
C(4M) C(3) S(2) 98.7(8) yes
C(4M) C(3) C(3M) 139.7(8) yes
H(3) C(3) C(4) 113.9(9) no
H(3) C(3) S(2) 96.9(6) no
H(3) C(3) C(3M) 142.7(11) no
H(3) C(3) C(4M) 63.5(7) no
H(31) C(3) C(4) 115.2(9) no
H(31) C(3) S(2) 115.8(6) no
H(31) C(3) C(3M) 105.6(10) no
H(31) C(3) C(4M) 93.0(9) no
H(31) C(3) H(3) 37.1(3) no
H(32) C(3) C(4) 115.5(9) no
H(32) C(3) S(2) 60.1(4) no
H(32) C(3) C(3M) 47.3(7) no
H(32) C(3) C(4M) 153.8(11) no
H(32) C(3) H(3) 129.7(8) no
H(32) C(3) H(31) 109.7(9) no
H(4MC) C(3) C(4) 85.7(9) no
H(4MC) C(3) S(2) 58.5(4) no
H(4MC) C(3) C(3M) 140.0(9) no
H(4MC) C(3) C(4M) 40.7(7) no
H(4MC) C(3) H(3) 77.3(7) no
H(4MC) C(3) H(31) 114.4(8) no
H(4MC) C(3) H(32) 114.8(8) no
S(3) C(4) C(3) 132.1(9) yes
C(3M) C(4) C(3) 63.2(9) yes
C(3M) C(4) S(3) 99.5(7) yes
C(4M) C(4) C(3) 75.7(9) yes
C(4M) C(4) S(3) 107.6(10) yes
C(4M) C(4) C(3M) 138.8(9) yes
H(4) C(4) C(3) 139.4(14) no
H(4) C(4) S(3) 62.2(5) no
H(4) C(4) C(3M) 77.7(9) no
H(4) C(4) C(4M) 142.6(11) no
H(41) C(4) C(3) 107.9(9) no
H(41) C(4) S(3) 106.8(8) no
H(41) C(4) C(3M) 148.8(12) no
H(41) C(4) C(4M) 46.2(8) no
H(41) C(4) H(4) 99.7(7) no
H(42) C(4) C(3) 98.9(11) no
H(42) C(4) S(3) 101.2(6) no
H(42) C(4) C(3M) 49.9(7) no
H(42) C(4) C(4M) 145.5(11) no
H(42) C(4) H(4) 43.4(5) no
H(42) C(4) H(41) 107.4(10) no
S(3) C(5) C(2) 128.6(5) yes
S(4) C(5) C(2) 116.3(5) yes
S(4) C(5) S(3) 115.1(3) yes
S(5) C(6) C(1) 123.5(4) yes
S(8) C(6) C(1) 122.7(4) yes
S(8) C(6) S(5) 113.8(3) yes
S(5) C(7) C(10) 117.0(4) yes
S(6) C(7) C(10) 123.7(4) yes
S(6) C(7) S(5) 119.0(3) yes
S(6) C(8) C(9) 120.7(6) yes
C(8M) C(8) C(9) 118.9(9) yes
C(8M) C(8) S(6) 112.3(7) yes
H(8) C(8) C(9) 91.7(7) no
H(8) C(8) S(6) 104.8(6) no
H(8) C(8) C(8M) 102.7(7) no
S(7) C(9) C(8) 123.0(7) yes
H(91) C(9) C(8) 111.2(8) no
H(91) C(9) S(7) 105.6(6) no
H(92) C(9) C(8) 103.9(8) no
H(92) C(9) S(7) 105.0(6) no
H(92) C(9) H(91) 106.9(8) no
S(7) C(10) C(7) 125.5(4) yes
S(8) C(10) C(7) 117.2(4) yes
S(8) C(10) S(7) 117.1(3) yes
C(2) S(1) C(1) 93.9(3) yes
C(3) S(2) C(2) 102.1(3) yes
H(32) S(2) C(2) 98.1(2) no
H(32) S(2) C(3) 36.7(4) no
H(4MC) S(2) C(2) 85.9(2) no
H(4MC) S(2) C(3) 42.3(4) no
H(4MC) S(2) H(32) 77.20(10) no
C(5) S(3) C(4) 100.6(4) yes
H(4) S(3) C(4) 37.4(4) no
H(4) S(3) C(5) 129.8(2) no
C(5) S(4) C(1) 94.5(3) yes
C(7) S(5) C(6) 93.9(2) yes
C(8) S(6) C(7) 99.2(4) yes
C(10) S(7) C(9) 101.0(4) yes
C(10) S(8) C(6) 93.7(2) yes
C(4) C(3M) C(3) 39.7(5) yes
H(32) C(3M) C(3) 38.6(6) no
H(32) C(3M) C(4) 73.9(8) no
H(3MA) C(3M) C(3) 109.0(14) no
H(3MA) C(3M) C(4) 92.3(12) no
H(3MA) C(3M) H(32) 138.0(17) no
H(3MB) C(3M) C(3) 110.5(13) no
H(3MB) C(3M) C(4) 91.5(11) no
H(3MB) C(3M) H(32) 99.0(13) no
H(3MB) C(3M) H(3MA) 121.3(15) no
H(3MC) C(3M) C(3) 101.0(10) no
H(3MC) C(3M) C(4) 140.7(12) no
H(3MC) C(3M) H(32) 69.3(8) no
H(3MC) C(3M) H(3MA) 105.8(14) no
H(3MC) C(3M) H(3MB) 107.1(15) no
H(42) C(3M) C(3) 69.5(8) no
H(42) C(3M) C(4) 37.9(5) no
H(42) C(3M) H(32) 107.9(12) no
H(42) C(3M) H(3MA) 55.5(8) no
H(42) C(3M) H(3MB) 102.3(12) no
H(42) C(3M) H(3MC) 150.5(15) no
C(4) C(4M) C(3) 41.7(6) yes
H(41) C(4M) C(3) 72.7(10) no
H(41) C(4M) C(4) 38.7(6) no
H(4MA) C(4M) C(3) 97.2(11) no
H(4MA) C(4M) C(4) 128.0(15) no
H(4MA) C(4M) H(41) 114.8(16) no
H(4MB) C(4M) C(3) 141.8(16) no
H(4MB) C(4M) C(4) 122.6(14) no
H(4MB) C(4M) H(41) 117.0(13) no
H(4MB) C(4M) H(4MA) 109.3(16) no
H(4MC) C(4M) C(3) 42.7(7) no
H(4MC) C(4M) C(4) 70.4(10) no
H(4MC) C(4M) H(41) 108.8(15) no
H(4MC) C(4M) H(4MA) 101.7(12) no
H(4MC) C(4M) H(4MB) 103.4(15) no
H(8MA) C(8M) C(8) 114.5(10) no
H(8MB) C(8M) C(8) 119.0(9) no
H(8MB) C(8M) H(8MA) 110.5(9) no
H(8MC) C(8M) C(8) 104.8(8) no
H(8MC) C(8M) H(8MA) 101.9(8) no
H(8MC) C(8M) H(8MB) 103.7(9) no
H(31) H(3) C(3) 70.8(6) no
H(3) H(31) C(3) 72.1(6) no
S(2) H(32) C(3) 83.2(6) no
C(3M) H(32) C(3) 94.2(9) no
C(3M) H(32) S(2) 157.4(8) no
S(3) H(4) C(4) 80.4(7) no
H(42) H(4) C(4) 72.4(7) no
H(42) H(4) S(3) 140.50(10) no
C(4M) H(41) C(4) 95.1(11) no
C(3M) H(42) C(4) 92.3(8) no
H(4) H(42) C(4) 64.1(5) no
H(4) H(42) C(3M) 117.0(7) no
S(2) H(4MC) C(3) 79.2(4) no
C(4M) H(4MC) C(3) 96.6(10) no
C(4M) H(4MC) S(2) 169.7(8) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C(6) C(1) . . 1.342(7) yes
S(1) C(1) . . 1.746(5) yes
S(4) C(1) . . 1.749(5) yes
C(5) C(2) . . 1.329(8) yes
S(1) C(2) . . 1.753(6) yes
S(2) C(2) . . 1.750(7) yes
C(4) C(3) . . 1.232(11) yes
S(2) C(3) . . 1.785(10) yes
C(3M) C(3) . . 1.72(2) yes
H(3) C(3) . . 1.090(9) no
H(31) C(3) . . 1.082(10) no
H(32) C(3) . . 1.076(10) no
H(4MC) C(3) . . 1.223(12) no
S(3) C(4) . . 1.768(11) yes
C(4M) C(4) . . 1.64(2) yes
H(4) C(4) . . 1.089(10) no
H(41) C(4) . . 1.032(11) no
H(42) C(4) . . 1.155(14) no
S(3) C(5) . . 1.746(6) yes
S(4) C(5) . . 1.759(6) yes
S(5) C(6) . . 1.755(5) yes
S(8) C(6) . . 1.754(5) yes
C(10) C(7) . . 1.342(8) yes
S(5) C(7) . . 1.751(6) yes
S(6) C(7) . . 1.736(6) yes
C(9) C(8) . . 1.394(11) yes
S(6) C(8) . . 1.787(9) yes
C(8M) C(8) . . 1.415(13) yes
H(8) C(8) . . 1.176(10) no
S(7) C(9) . . 1.792(9) yes
H(91) C(9) . . 1.092(9) no
H(92) C(9) . . 1.103(11) no
S(7) C(10) . . 1.737(6) yes
S(8) C(10) . . 1.754(5) yes
H(32) S(2) . . 1.558(3) no
H(4MC) S(2) . . 1.549(2) no
H(4) S(3) . . 1.587(3) no
H(32) C(3M) . . 1.267(15) no
H(3MA) C(3M) . . 1.021(17) no
H(3MB) C(3M) . . 1.002(17) no
H(3MC) C(3M) . . 1.186(15) no
H(41) C(4M) . . 1.190(17) no
H(4MA) C(4M) . . 1.095(17) no
H(4MB) C(4M) . . 1.067(18) no
H(4MC) C(4M) . . 1.178(18) no
H(8MA) C(8M) . . 1.088(10) no
H(8MB) C(8M) . . 1.058(11) no
H(8MC) C(8M) . . 1.182(11) no
H(31) H(3) . . 0.691 no
H(42) H(4) . . 0.833 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S(3) S(2) 3.533(3) 1_655 no
S(4) S(2) 3.434(3) 1_655 no
S(7) S(6) 3.703(3) 1_655 no
S(5) S(8) 3.585(2) 3_655 no
S(1) S(5) 3.572(2) 3 no
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
S(1) C(1) C(6) S(5) 0.6(6) no
S(4) C(1) C(6) S(5) 179.3(3) no
S(1) C(1) C(6) S(8) -176.7(3) no
S(4) C(1) C(6) S(8) 2.0(6) no
C(6) C(1) S(1) C(2) -161.7(5) no
S(4) C(1) S(1) C(2) 19.4(3) no
C(6) C(1) S(4) C(5) 162.5(5) no
S(1) C(1) S(4) C(5) -18.6(3) no
S(1) C(2) C(5) S(3) -174.9(4) no
S(2) C(2) C(5) S(3) 1.6(10) no
S(1) C(2) C(5) S(4) 2.2(7) no
S(2) C(2) C(5) S(4) 178.6(4) no
C(5) C(2) S(1) C(1) -13.2(6) no
S(2) C(2) S(1) C(1) 169.9(4) no
C(5) C(2) S(2) C(3) -4.8(8) no
S(1) C(2) S(2) C(3) 171.7(4) no
S(2) C(3) C(4) S(3) -20.4(17) no
C(3M) C(3) C(4) S(3) 78.1(12) no
S(2) C(3) C(4) C(4M) 80.4(11) no
C(4) C(3) S(2) C(2) 13.8(11) no
C(3M) C(3) S(2) C(2) -70.5(8) no
C(3) C(4) S(3) C(5) 13.1(13) no
C(4M) C(4) S(3) C(5) -73.2(9) no
C(2) C(5) S(3) C(4) -2.8(8) no
S(4) C(5) S(3) C(4) -180.0(5) no
C(2) C(5) S(4) C(1) 10.0(6) no
S(3) C(5) S(4) C(1) -172.5(4) no
C(1) C(6) S(5) C(7) 162.2(4) no
S(8) C(6) S(5) C(7) -20.3(3) no
C(1) C(6) S(8) C(10) -162.1(4) no
S(5) C(6) S(8) C(10) 20.3(3) no
S(5) C(7) C(10) S(7) 174.7(3) no
S(6) C(7) C(10) S(7) 1.3(8) no
S(5) C(7) C(10) S(8) 0.2(6) no
S(6) C(7) C(10) S(8) -173.1(3) no
C(10) C(7) S(5) C(6) 12.1(5) no
S(6) C(7) S(5) C(6) -174.2(3) no
C(10) C(7) S(6) C(8) 39.8(6) no
S(5) C(7) S(6) C(8) -133.4(4) no
S(6) C(8) C(9) S(7) 17.1(11) no
C(8M) C(8) C(9) S(7) 163.1(7) no
C(9) C(8) S(6) C(7) -48.3(8) no
C(8M) C(8) S(6) C(7) 163.6(7) no
C(8) C(9) S(7) C(10) 24.9(8) no
C(7) C(10) S(7) C(9) -35.8(6) no
S(8) C(10) S(7) C(9) 138.6(4) no
C(7) C(10) S(8) C(6) -12.5(5) no
S(7) C(10) S(8) C(6) 172.6(3) no
