#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/67/2236769.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_2236769
loop_
_publ_author_name
'Suarez, Sebastian A.'
'Hazari, Saroj K. S.'
'Ganguly, Biplab'
'Doctorovich, Fabio'
'G. Roy, Tapashi'
'Baggio, Ricardo'
_publ_section_title
;
 3-Methyl-5-methylsulfanyl-1,3,4-thiadiazole-2(3H)-thione
;
_journal_coeditor_code           ZL2506
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3045
_journal_page_last               o3046
_journal_paper_doi               10.1107/S1600536812040147
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C4 H6 N2 S3'
_chemical_formula_moiety         'C4 H6 N2 S3'
_chemical_formula_sum            'C4 H6 N2 S3'
_chemical_formula_weight         178.30
_chemical_name_systematic
;
3-Methyl-5-methylsulfanyl-1,3,4-thiadiazole-2(3H)-thione
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 106.661(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   9.3505(4)
_cell_length_b                   22.4118(9)
_cell_length_c                   7.6682(5)
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0065
_cell_measurement_theta_min      3.5361
_cell_volume                     1539.50(14)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Oxford Diffraction Gemini CCD S Ultra'
_diffrn_measurement_method       'ω scans, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32965
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29.07
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.5703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                2690
_reflns_number_total             3821
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2506.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' -P 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236769
_cod_database_fobs_code          2236769
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
C C3 0.3939(3) 0.57279(10) 0.1948(4) 0.0553(6) Uani d . 1
H H3A 0.4718 0.5836 0.3019 0.083 Uiso calc R 1
H H3B 0.3252 0.6054 0.159 0.083 Uiso calc R 1
H H3C 0.4366 0.5637 0.098 0.083 Uiso calc R 1
C C4 -0.1404(3) 0.54132(12) 0.2162(4) 0.0595(7) Uani d . 1
H H4A -0.0915 0.5686 0.3112 0.089 Uiso calc R 1
H H4B -0.2458 0.5414 0.2022 0.089 Uiso calc R 1
H H4C -0.1228 0.5534 0.1041 0.089 Uiso calc R 1
C C7 0.0292(3) 0.67498(11) 0.0189(4) 0.0588(7) Uani d . 1
H H7A -0.0033 0.6733 0.1267 0.088 Uiso calc R 1
H H7B 0.0849 0.6396 0.011 0.088 Uiso calc R 1
H H7C -0.0561 0.6776 -0.0863 0.088 Uiso calc R 1
C C8 0.5833(3) 0.70055(13) 0.0599(4) 0.0654(7) Uani d . 1
H H8A 0.57 0.6818 0.1668 0.098 Uiso calc R 1
H H8B 0.6867 0.6988 0.0635 0.098 Uiso calc R 1
H H8C 0.5243 0.6801 -0.0464 0.098 Uiso calc R 1
S S3 0.55055(7) 0.44639(3) 0.29305(10) 0.05657(19) Uani d . 1
S S1 0.24366(7) 0.42026(3) 0.32098(9) 0.04892(17) Uani d . 1
S S2 -0.06774(7) 0.46747(3) 0.27437(9) 0.05080(17) Uani d . 1
N N1 0.3150(2) 0.52053(8) 0.2336(3) 0.0406(4) Uani d . 1
N N2 0.1669(2) 0.52810(8) 0.2290(3) 0.0420(4) Uani d . 1
C C1 0.3770(2) 0.46736(9) 0.2779(3) 0.0404(5) Uani d . 1
C C2 0.1153(2) 0.47832(10) 0.2715(3) 0.0414(5) Uani d . 1
S S6 -0.09695(7) 0.80636(3) 0.00218(11) 0.0622(2) Uani d . 1
S S4 0.22529(7) 0.83027(3) 0.03346(10) 0.05732(19) Uani d . 1
S S5 0.52524(7) 0.77719(3) 0.05225(10) 0.0598(2) Uani d . 1
N N3 0.1238(2) 0.72729(8) 0.0269(3) 0.0432(4) Uani d . 1
N N4 0.2722(2) 0.71785(8) 0.0383(3) 0.0469(5) Uani d . 1
C C5 0.0747(2) 0.78324(10) 0.0200(3) 0.0427(5) Uani d . 1
C C6 0.3387(3) 0.76844(10) 0.0417(3) 0.0445(5) Uani d . 1
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.125 0.123 '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
N1 C3 H3A 109.5
N1 C3 H3B 109.5
H3A C3 H3B 109.5
N1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
S2 C4 H4A 109.5
S2 C4 H4B 109.5
H4A C4 H4B 109.5
S2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N3 C7 H7A 109.5
N3 C7 H7B 109.5
H7A C7 H7B 109.5
N3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
S5 C8 H8A 109.5
S5 C8 H8B 109.5
H8A C8 H8B 109.5
S5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C1 S1 C2 89.52(10)
C2 S2 C4 99.90(11)
C1 N1 N2 118.46(17)
C1 N1 C3 124.32(19)
N2 N1 C3 117.18(17)
C2 N2 N1 109.28(18)
N1 C1 S3 128.21(17)
N1 C1 S1 108.08(16)
S3 C1 S1 123.71(13)
N2 C2 S2 124.35(18)
N2 C2 S1 114.66(17)
S2 C2 S1 120.96(13)
C6 S4 C5 89.64(11)
C6 S5 C8 100.60(12)
C5 N3 N4 118.36(18)
C5 N3 C7 123.90(19)
N4 N3 C7 117.72(18)
C6 N4 N3 109.63(18)
N3 C5 S6 127.83(17)
N3 C5 S4 107.77(16)
S6 C5 S4 124.40(14)
N4 C6 S5 124.94(18)
N4 C6 S4 114.57(17)
S5 C6 S4 120.49(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 N1 1.460(3)
C3 H3A 0.96
C3 H3B 0.96
C3 H3C 0.96
C4 S2 1.796(3)
C4 H4A 0.96
C4 H4B 0.96
C4 H4C 0.96
C7 N3 1.459(3)
C7 H7A 0.96
C7 H7B 0.96
C7 H7C 0.96
C8 S5 1.797(3)
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
S3 C1 1.662(2)
S1 C1 1.736(2)
S1 C2 1.737(2)
S2 C2 1.735(2)
N1 C1 1.326(3)
N1 N2 1.385(2)
N2 C2 1.294(3)
S6 C5 1.655(2)
S4 C6 1.735(2)
S4 C5 1.738(2)
S5 C6 1.734(2)
N3 C5 1.331(3)
N3 N4 1.382(3)
N4 C6 1.289(3)
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
S3 S2 3.6438(10) 1_655 y
S2 S2 3.6319(9) 3_566 y
S6 S5 3.7189(11) 1_455 y
S3 S4 3.3671(10) 2_645 y
S1 S6 3.3621(10) 2_545 y
S1 S5 3.8332(11) 2_645 y
S2 S4 3.8778(10) 2_545 y
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
C4 H4C Cg1 3_565 0.96 2.86 3.589(3) 134
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4481224
