#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/98/2209814.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_2209814
loop_
_publ_author_name
'Xiao-Lan Lu'
'Wen-Zhao Bi'
'Yu-Qing Shang'
'Liang-Zhong Xu'
'Guan-Ping Yu'
_publ_section_title
4-(2-Nitrobenzylideneamino)-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione
_journal_coeditor_code           CV2064
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3189
_journal_page_last               o3190
_journal_paper_doi               10.1107/S1600536806022082
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H10 N8 O2 S'
_chemical_formula_moiety         'C12 H10 N8 O2 S'
_chemical_formula_sum            'C12 H10 N8 O2 S'
_chemical_formula_weight         330.34
_chemical_name_systematic
;4-(2-Nitrobenzylideneamino)-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-
5(4H)-thione
;
_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'
_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                 105.345(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.421(2)
_cell_length_b                   8.1070(14)
_cell_length_c                   16.446(3)
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.52
_cell_volume                     1468.5(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8026
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0428
_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)+(0.0393P)²+0.548P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                1894
_reflns_number_total             2991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2064.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209814
_cod_database_fobs_code          2209814
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.59893(6) 0.69127(10) 0.62340(4) 0.0568(2) Uani d . 1
O O1 0.7180(2) 0.6319(3) 0.45292(16) 0.0877(8) Uani d . 1
O O2 0.7361(2) 0.4553(3) 0.35946(18) 0.1013(9) Uani d . 1
N N1 0.6874(2) 0.5739(3) 0.3820(2) 0.0661(7) Uani d . 1
N N2 0.40527(17) 0.8406(2) 0.44138(11) 0.0400(5) Uani d . 1
N N3 0.39256(16) 0.8451(2) 0.52331(11) 0.0335(5) Uani d . 1
N N4 0.41264(18) 0.8584(3) 0.65536(12) 0.0412(5) Uani d . 1
H H4A 0.438(2) 0.842(3) 0.7099(17) 0.056(8) Uiso d . 1
N N5 0.30740(17) 0.9419(2) 0.61942(11) 0.0404(5) Uani d . 1
N N6 0.11614(16) 0.8818(3) 0.42617(11) 0.0375(5) Uani d . 1
N N7 0.05211(19) 0.7839(3) 0.46600(13) 0.0536(6) Uani d . 1
N N8 0.0092(2) 0.7219(3) 0.32815(13) 0.0553(6) Uani d . 1
C C1 0.4790(2) 0.7390(3) 0.42440(15) 0.0425(6) Uani d . 1
H H1 0.5218 0.6659 0.4651 0.051 Uiso calc R 1
C C2 0.4954(2) 0.7389(3) 0.33855(15) 0.0416(6) Uani d . 1
C C3 0.4123(2) 0.8181(4) 0.27341(15) 0.0526(7) Uani d . 1
H H3 0.3455 0.8698 0.2845 0.063 Uiso calc R 1
C C4 0.4263(3) 0.8221(4) 0.19243(17) 0.0651(9) Uani d . 1
H H4 0.3697 0.8766 0.1498 0.078 Uiso calc R 1
C C5 0.5252(3) 0.7444(4) 0.1750(2) 0.0729(10) Uani d . 1
H H5 0.5356 0.7484 0.1208 0.087 Uiso calc R 1
C C6 0.6067(3) 0.6626(4) 0.2370(2) 0.0687(9) Uani d . 1
H H6 0.6720 0.6086 0.2249 0.082 Uiso calc R 1
C C7 0.5927(2) 0.6597(3) 0.31775(18) 0.0513(7) Uani d . 1
C C8 0.4685(2) 0.7967(3) 0.60077(14) 0.0370(6) Uani d . 1
C C9 0.29860(19) 0.9337(3) 0.53949(13) 0.0333(5) Uani d . 1
C C10 0.1982(2) 1.0076(3) 0.47272(14) 0.0394(6) Uani d . 1
H H10A 0.1530 1.0837 0.4984 0.047 Uiso calc R 1
H H10B 0.2321 1.0696 0.4339 0.047 Uiso calc R 1
C C11 0.0892(2) 0.8421(3) 0.34524(15) 0.0489(7) Uani d . 1
H H11 0.1225 0.8925 0.3057 0.059 Uiso calc R 1
C C12 -0.0098(2) 0.6914(4) 0.40393(16) 0.0559(7) Uani d . 1
H H12 -0.0633 0.6102 0.4119 0.067 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
O2 N1 O1 123.9(3)
O2 N1 C7 117.6(3)
O1 N1 C7 118.3(2)
C1 N2 N3 118.5(2)
C9 N3 N2 119.14(17)
C9 N3 C8 107.40(18)
N2 N3 C8 132.64(19)
C8 N4 N5 114.70(18)
C8 N4 H4A 123.3(17)
N5 N4 H4A 121.9(17)
C9 N5 N4 103.68(18)
C11 N6 N7 109.3(2)
C11 N6 C10 130.1(2)
N7 N6 C10 120.58(18)
C12 N7 N6 101.9(2)
C11 N8 C12 102.3(2)
N2 C1 C2 118.3(2)
N2 C1 H1 120.8
C2 C1 H1 120.8
C3 C2 C7 116.6(2)
C3 C2 C1 120.3(2)
C7 C2 C1 123.0(2)
C4 C3 C2 121.7(3)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 119.7(3)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 120.1(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 120.0(3)
C5 C6 H6 120.0
C7 C6 H6 120.0
C6 C7 C2 121.9(3)
C6 C7 N1 116.7(3)
C2 C7 N1 121.4(2)
N4 C8 N3 102.6(2)
N4 C8 S1 126.92(17)
N3 C8 S1 130.51(18)
N5 C9 N3 111.64(19)
N5 C9 C10 124.5(2)
N3 C9 C10 123.80(19)
N6 C10 C9 111.64(19)
N6 C10 H10A 109.3
C9 C10 H10A 109.3
N6 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 108.0
N8 C11 N6 111.0(2)
N8 C11 H11 124.5
N6 C11 H11 124.5
N7 C12 N8 115.5(3)
N7 C12 H12 122.3
N8 C12 H12 122.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.672(2)
O1 N1 1.220(3)
O2 N1 1.216(3)
N1 C7 1.472(4)
N2 C1 1.261(3)
N2 N3 1.393(2)
N3 C9 1.375(3)
N3 C8 1.394(3)
N4 C8 1.329(3)
N4 N5 1.370(3)
N4 H4A 0.88(3)
N5 C9 1.293(3)
N6 C11 1.324(3)
N6 N7 1.359(3)
N6 C10 1.458(3)
N7 C12 1.312(3)
N8 C11 1.314(3)
N8 C12 1.344(3)
C1 C2 1.473(3)
C1 H1 0.9300
C2 C3 1.387(4)
C2 C7 1.402(3)
C3 C4 1.383(3)
C3 H3 0.9300
C4 C5 1.387(5)
C4 H4 0.9300
C5 C6 1.357(5)
C5 H5 0.9300
C6 C7 1.380(4)
C6 H6 0.9300
C9 C10 1.487(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11 0.9300
C12 H12 0.9300
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
N4 H4A N8 4_676 0.88(3) 1.97(3) 2.838(3) 171(2)
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
C1 N2 N3 C9 -168.9(2)
C1 N2 N3 C8 22.9(4)
C8 N4 N5 C9 -0.9(3)
C11 N6 N7 C12 -0.2(3)
C10 N6 N7 C12 179.4(2)
N3 N2 C1 C2 -177.79(19)
N2 C1 C2 C3 -15.5(4)
N2 C1 C2 C7 165.2(2)
C7 C2 C3 C4 -1.5(4)
C1 C2 C3 C4 179.1(2)
C2 C3 C4 C5 0.4(4)
C3 C4 C5 C6 1.1(4)
C4 C5 C6 C7 -1.4(4)
C5 C6 C7 C2 0.2(4)
C5 C6 C7 N1 -177.7(3)
C3 C2 C7 C6 1.2(4)
C1 C2 C7 C6 -179.4(2)
C3 C2 C7 N1 179.0(2)
C1 C2 C7 N1 -1.6(4)
O2 N1 C7 C6 -32.7(4)
O1 N1 C7 C6 142.5(3)
O2 N1 C7 C2 149.3(3)
O1 N1 C7 C2 -35.4(4)
N5 N4 C8 N3 0.1(3)
N5 N4 C8 S1 179.03(17)
C9 N3 C8 N4 0.8(2)
N2 N3 C8 N4 170.0(2)
C9 N3 C8 S1 -178.13(19)
N2 N3 C8 S1 -8.9(4)
N4 N5 C9 N3 1.4(2)
N4 N5 C9 C10 -179.8(2)
N2 N3 C9 N5 -172.38(19)
C8 N3 C9 N5 -1.5(3)
N2 N3 C9 C10 8.8(3)
C8 N3 C9 C10 179.7(2)
C11 N6 C10 C9 -118.1(3)
N7 N6 C10 C9 62.4(3)
N5 C9 C10 N6 -107.2(3)
N3 C9 C10 N6 71.4(3)
C12 N8 C11 N6 -0.3(3)
N7 N6 C11 N8 0.3(3)
C10 N6 C11 N8 -179.2(2)
N6 N7 C12 N8 0.0(3)
C11 N8 C12 N7 0.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179008
