#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216055.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_2216055
loop_
_publ_author_name
'Wang, Pin-Liang'
'Kang, Si-Shun'
'Li, Hai-Ling'
'Zeng, Hai-Su'
'Wang, Hai-Bo'
_publ_section_title
2-Methyl-5-[3-(4-nitrophenyl)-1,2,4-oxadiazol-5-ylmethylenesulfanyl]-1,3,4-thiadiazole
_journal_coeditor_code           LW2036
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4236
_journal_page_last               o4236
_journal_paper_doi               10.1107/S1600536807047812
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H9 N5 O3 S2'
_chemical_formula_moiety         'C12 H9 N5 O3 S2'
_chemical_formula_sum            'C12 H9 N5 O3 S2'
_chemical_formula_weight         335.36
_chemical_name_systematic
;
2-Methyl-5-[3-(4-nitrophenyl)-1,2,4-oxadiazol-5-ylmethylenesulfanyl]-1,3,4-
thiadiazole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.939(7)
_cell_length_b                   5.6540(11)
_cell_length_c                   13.714(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2783.9(10)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2772
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.9237
_exptl_absorpt_correction_T_min  0.8554
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1P)²+10P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.2120
_reflns_number_gt                1965
_reflns_number_total             2727
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lw2036.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C  2yc'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2216055
_cod_database_fobs_code          2216055
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_refinement_flags
_atom_site_occupancy
S S1 0.48917(3) 0.5272(2) 0.62377(9) 0.0525(4) Uani d . 1
S S2 0.56945(4) 0.6940(2) 0.64667(10) 0.0565(4) Uani d . 1
O O1 0.61049(9) 0.4474(6) 0.4886(2) 0.0542(9) Uani d . 1
O O2 0.75292(12) -0.7027(8) 0.3772(3) 0.0766(12) Uani d . 1
O O3 0.72006(12) -0.6820(7) 0.2417(3) 0.0709(11) Uani d . 1
N N1 0.51318(12) 0.1027(8) 0.6228(3) 0.0598(11) Uani d . 1
N N2 0.54470(11) 0.2462(8) 0.6310(3) 0.0554(10) Uani d . 1
N N3 0.64182(10) 0.1824(7) 0.5757(3) 0.0465(9) Uani d . 1
N N4 0.62608(11) 0.2924(7) 0.4218(3) 0.0516(10) Uani d . 1
N N5 0.72802(12) -0.6150(8) 0.3256(3) 0.0541(10) Uani d . 1
C C1 0.44496(15) 0.1124(11) 0.6123(4) 0.0652(14) Uani d . 1
H H1B 0.4420 0.0103 0.6673 0.098 Uiso calc R 1
H H1C 0.4425 0.0218 0.5532 0.098 Uiso calc R 1
H H1D 0.4262 0.2334 0.6115 0.098 Uiso calc R 1
C C2 0.48254(14) 0.2238(9) 0.6198(3) 0.0522(12) Uani d . 1
C C3 0.53603(13) 0.4704(8) 0.6337(3) 0.0465(11) Uani d . 1
C C4 0.61043(14) 0.5081(10) 0.6631(4) 0.0594(13) Uani d . 1
H H4B 0.6314 0.6079 0.6830 0.071 Uiso calc R 1
H H4C 0.6064 0.3991 0.7162 0.071 Uiso calc R 1
C C5 0.62069(12) 0.3713(8) 0.5783(3) 0.0447(10) Uani d . 1
C C6 0.64432(12) 0.1382(8) 0.4777(3) 0.0447(10) Uani d . 1
C C7 0.66602(11) -0.0549(7) 0.4390(3) 0.0401(9) Uani d . 1
C C8 0.68800(12) -0.2013(8) 0.5007(3) 0.0462(11) Uani d . 1
H H8A 0.6887 -0.1742 0.5677 0.055 Uiso calc R 1
C C9 0.70838(12) -0.3833(9) 0.4645(3) 0.0488(11) Uani d . 1
H H9A 0.7227 -0.4804 0.5060 0.059 Uiso calc R 1
C C10 0.70704(12) -0.4188(8) 0.3649(3) 0.0445(10) Uani d . 1
C C11 0.68665(13) -0.2755(8) 0.3014(3) 0.0482(11) Uani d . 1
H H11A 0.6870 -0.3000 0.2344 0.058 Uiso calc R 1
C C12 0.66587(12) -0.0965(9) 0.3382(3) 0.0481(11) Uani d . 1
H H12A 0.6515 -0.0015 0.2959 0.058 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 S1 C2 87.2(2)
C3 S2 C4 98.3(2)
C5 O1 N4 107.4(3)
C2 N1 N2 112.4(4)
C3 N2 N1 111.9(4)
C5 N3 C6 103.8(4)
C6 N4 O1 103.7(4)
O2 N5 O3 123.3(4)
O2 N5 C10 118.2(4)
O3 N5 C10 118.4(4)
C2 C1 H1B 109.5
C2 C1 H1C 109.5
H1B C1 H1C 109.5
C2 C1 H1D 109.5
H1B C1 H1D 109.5
H1C C1 H1D 109.5
N1 C2 C1 123.0(5)
N1 C2 S1 114.0(4)
C1 C2 S1 123.0(4)
N2 C3 S1 114.5(4)
N2 C3 S2 122.8(4)
S1 C3 S2 122.8(3)
C5 C4 S2 116.2(4)
C5 C4 H4B 108.2
S2 C4 H4B 108.2
C5 C4 H4C 108.2
S2 C4 H4C 108.2
H4B C4 H4C 107.4
N3 C5 O1 111.8(4)
N3 C5 C4 128.4(4)
O1 C5 C4 119.6(4)
N4 C6 N3 113.4(4)
N4 C6 C7 123.1(4)
N3 C6 C7 123.5(4)
C8 C7 C12 118.3(4)
C8 C7 C6 121.3(4)
C12 C7 C6 120.4(4)
C9 C8 C7 121.4(4)
C9 C8 H8A 119.3
C7 C8 H8A 119.3
C8 C9 C10 118.2(4)
C8 C9 H9A 120.9
C10 C9 H9A 120.9
C11 C10 C9 122.3(4)
C11 C10 N5 118.9(4)
C9 C10 N5 118.7(4)
C12 C11 C10 119.1(4)
C12 C11 H11A 120.4
C10 C11 H11A 120.4
C11 C12 C7 120.6(4)
C11 C12 H12A 119.7
C7 C12 H12A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.714(5)
S1 C2 1.732(6)
S2 C3 1.747(5)
S2 C4 1.815(5)
O1 C5 1.340(5)
O1 N4 1.402(5)
O2 N5 1.221(5)
O3 N5 1.232(5)
N1 C2 1.296(6)
N1 N2 1.394(6)
N2 C3 1.307(6)
N3 C5 1.312(6)
N3 C6 1.374(6)
N4 C6 1.316(6)
N5 C10 1.458(6)
C1 C2 1.490(7)
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
C4 C5 1.457(7)
C4 H4B 0.9700
C4 H4C 0.9700
C6 C7 1.456(6)
C7 C8 1.402(6)
C7 C12 1.402(6)
C8 C9 1.369(7)
C8 H8A 0.9300
C9 C10 1.380(6)
C9 H9A 0.9300
C10 C11 1.376(6)
C11 C12 1.367(7)
C11 H11A 0.9300
C12 H12A 0.9300
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
C2 N1 N2 C3 0.0(6)
C5 O1 N4 C6 -0.2(4)
N2 N1 C2 C1 -179.3(4)
N2 N1 C2 S1 1.5(6)
C3 S1 C2 N1 -1.9(4)
C3 S1 C2 C1 178.9(4)
N1 N2 C3 S1 -1.5(5)
N1 N2 C3 S2 178.4(3)
C2 S1 C3 N2 1.9(4)
C2 S1 C3 S2 -178.0(3)
C4 S2 C3 N2 -4.6(5)
C4 S2 C3 S1 175.3(3)
C3 S2 C4 C5 68.1(5)
C6 N3 C5 O1 -0.8(5)
C6 N3 C5 C4 -175.6(5)
N4 O1 C5 N3 0.7(5)
N4 O1 C5 C4 176.0(4)
S2 C4 C5 N3 -160.2(4)
S2 C4 C5 O1 25.4(6)
O1 N4 C6 N3 -0.3(5)
O1 N4 C6 C7 -178.2(4)
C5 N3 C6 N4 0.7(5)
C5 N3 C6 C7 178.6(4)
N4 C6 C7 C8 173.6(4)
N3 C6 C7 C8 -4.1(7)
N4 C6 C7 C12 -5.3(7)
N3 C6 C7 C12 176.9(4)
C12 C7 C8 C9 -1.1(7)
C6 C7 C8 C9 179.9(4)
C7 C8 C9 C10 0.5(7)
C8 C9 C10 C11 1.3(7)
C8 C9 C10 N5 -178.8(4)
O2 N5 C10 C11 161.8(4)
O3 N5 C10 C11 -17.3(6)
O2 N5 C10 C9 -18.1(7)
O3 N5 C10 C9 162.8(4)
C9 C10 C11 C12 -2.4(7)
N5 C10 C11 C12 177.7(4)
C10 C11 C12 C7 1.7(7)
C8 C7 C12 C11 0.0(7)
C6 C7 C12 C11 179.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21121209
