#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/70/2207009.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_2207009
loop_
_publ_author_name
'Xu, Liang-Zhong'
'Yu, Guan-Ping'
'Huang, Yong-Wei'
'Si, Guo-Dong'
'Li, Kai'
_publ_section_title
1-(4-Phenyl-3-thioxo-1,2,4-triazolidin-1-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3403
_journal_page_last               o3404
_journal_paper_doi               10.1107/S1600536805029867
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H12 N6 O S'
_chemical_formula_moiety         'C12 H12 N6 O S'
_chemical_formula_sum            'C12 H12 N6 O S'
_chemical_formula_weight         288.34
_chemical_name_systematic
1-(4-phenyl-3-thioxo-1,2,4-triazolidin-1-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone
_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                90.00
_cell_angle_beta                 107.362(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7112(19)
_cell_length_b                   13.589(3)
_cell_length_c                   10.711(2)
_cell_measurement_reflns_used    1493
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.49
_cell_volume                     1349.1(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7473
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0448
_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)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                1557
_reflns_number_total             2748
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6499.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_cell_volume        1349.0(5)
_cod_original_sg_symbol_Hall     '-P 2yb c'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207009
_cod_database_fobs_code          2207009
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_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_type_symbol
S1 0.48455(8) 0.68174(5) 0.45003(8) 0.0515(3) Uani d . 1 S
N1 0.7120(2) 0.56074(15) 0.5107(2) 0.0385(5) Uani d . 1 N
N2 0.7714(2) 0.48294(13) 0.45398(19) 0.0373(5) Uani d . 1 N
N3 0.5567(2) 0.52994(13) 0.3165(2) 0.0369(5) Uani d . 1 N
N4 1.0114(2) 0.35454(14) 0.7346(2) 0.0401(5) Uani d . 1 N
N5 1.1473(2) 0.35944(16) 0.7252(3) 0.0594(7) Uani d . 1 N
N6 1.1158(3) 0.21997(15) 0.8267(3) 0.0590(7) Uani d . 1 N
O1 0.8705(2) 0.33348(13) 0.47776(19) 0.0574(6) Uani d . 1 O
C1 0.5844(3) 0.58960(16) 0.4231(3) 0.0363(6) Uani d . 1 C
C2 0.6739(3) 0.46062(17) 0.3252(3) 0.0409(6) Uani d . 1 C
H2A 0.6404 0.3931 0.3199 0.049 Uiso calc R 1 H
H2B 0.7191 0.4724 0.2572 0.049 Uiso calc R 1 H
C3 0.4306(3) 0.52904(17) 0.2071(2) 0.0376(6) Uani d . 1 C
C4 0.3803(3) 0.6128(2) 0.1361(3) 0.0542(8) Uani d . 1 C
H4 0.4289 0.6721 0.1596 0.065 Uiso calc R 1 H
C5 0.2584(3) 0.6090(2) 0.0305(3) 0.0638(9) Uani d . 1 C
H5 0.2251 0.6659 -0.0172 0.077 Uiso calc R 1 H
C6 0.1857(3) 0.5229(3) -0.0051(3) 0.0707(10) Uani d . 1 C
H6 0.1025 0.5211 -0.0760 0.085 Uiso calc R 1 H
C7 0.2361(4) 0.4389(2) 0.0644(4) 0.0838(11) Uani d . 1 C
H7 0.1872 0.3798 0.0399 0.101 Uiso calc R 1 H
C8 0.3591(3) 0.4414(2) 0.1705(3) 0.0635(9) Uani d . 1 C
H8 0.3933 0.3842 0.2170 0.076 Uiso calc R 1 H
C9 0.8478(3) 0.40966(18) 0.5286(3) 0.0381(6) Uani d . 1 C
C10 0.9068(3) 0.42941(17) 0.6733(2) 0.0426(7) Uani d . 1 C
H10A 0.9522 0.4937 0.6874 0.051 Uiso calc R 1 H
H10B 0.8286 0.4293 0.7123 0.051 Uiso calc R 1 H
C11 0.9964(3) 0.27200(18) 0.7938(3) 0.0497(7) Uani d . 1 C
H11 0.9115 0.2529 0.8103 0.060 Uiso calc R 1 H
C12 1.2040(3) 0.2771(2) 0.7814(3) 0.0657(9) Uani d . 1 C
H12 1.2987 0.2592 0.7895 0.079 Uiso calc R 1 H
H1 0.770(3) 0.606(2) 0.541(3) 0.065(10) Uiso d . 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'
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
C1 N1 N2 108.6(2)
C1 N1 H1 115.0(19)
N2 N1 H1 114(2)
C9 N2 N1 121.0(2)
C9 N2 C2 119.65(19)
N1 N2 C2 109.12(18)
C1 N3 C3 127.2(2)
C1 N3 C2 112.1(2)
C3 N3 C2 120.74(19)
C11 N4 N5 109.1(2)
C11 N4 C10 130.7(2)
N5 N4 C10 119.9(2)
C12 N5 N4 102.1(2)
C11 N6 C12 101.5(2)
N3 C1 N1 108.5(2)
N3 C1 S1 128.0(2)
N1 C1 S1 123.55(19)
N2 C2 N3 101.59(18)
N2 C2 H2A 111.5
N3 C2 H2A 111.5
N2 C2 H2B 111.5
N3 C2 H2B 111.5
H2A C2 H2B 109.3
C4 C3 C8 119.6(3)
C4 C3 N3 121.7(2)
C8 C3 N3 118.7(2)
C5 C4 C3 120.1(3)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 120.7(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 119.5(3)
C5 C6 H6 120.2
C7 C6 H6 120.2
C6 C7 C8 120.4(3)
C6 C7 H7 119.8
C8 C7 H7 119.8
C3 C8 C7 119.7(3)
C3 C8 H8 120.2
C7 C8 H8 120.2
O1 C9 N2 120.1(2)
O1 C9 C10 123.1(2)
N2 C9 C10 116.7(2)
N4 C10 C9 109.9(2)
N4 C10 H10A 109.7
C9 C10 H10A 109.7
N4 C10 H10B 109.7
C9 C10 H10B 109.7
H10A C10 H10B 108.2
N6 C11 N4 111.8(2)
N6 C11 H11 124.1
N4 C11 H11 124.1
N5 C12 N6 115.5(2)
N5 C12 H12 122.2
N6 C12 H12 122.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.661(2) yes
N1 C1 1.369(3) yes
N1 N2 1.425(3) yes
N1 H1 0.83(3) ?
N2 C9 1.352(3) ?
N2 C2 1.453(3) ?
N3 C1 1.360(3) ?
N3 C3 1.420(3) ?
N3 C2 1.459(3) ?
N4 C11 1.318(3) yes
N4 N5 1.355(3) yes
N4 C10 1.449(3) ?
N5 C12 1.312(3) yes
N6 C11 1.313(3) yes
N6 C12 1.349(3) yes
O1 C9 1.220(3) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.375(3) ?
C3 C8 1.375(3) ?
C4 C5 1.372(4) ?
C4 H4 0.9300 ?
C5 C6 1.361(4) ?
C5 H5 0.9300 ?
C6 C7 1.371(4) ?
C6 H6 0.9300 ?
C7 C8 1.382(4) ?
C7 H7 0.9300 ?
C8 H8 0.9300 ?
C9 C10 1.507(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
N1 H1 N6 2_756 0.83(3) 2.16(3) 2.962(3) 160(3)
C2 H2B N5 3_766 0.97 2.61 3.138(3) 114.7
C5 H5 O1 2_655 0.93 2.54 3.288(4) 137.5
C11 H11 O1 4_566 0.93 2.28 2.978(3) 131.8
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 N1 N2 C9 -146.4(2)
C1 N1 N2 C2 -1.4(3)
C11 N4 N5 C12 -0.1(3)
C10 N4 N5 C12 -174.9(2)
C3 N3 C1 N1 174.7(2)
C2 N3 C1 N1 -4.1(3)
C3 N3 C1 S1 -4.4(4)
C2 N3 C1 S1 176.81(18)
N2 N1 C1 N3 3.3(3)
N2 N1 C1 S1 -177.53(16)
C9 N2 C2 N3 144.6(2)
N1 N2 C2 N3 -0.9(2)
C1 N3 C2 N2 3.1(2)
C3 N3 C2 N2 -175.8(2)
C1 N3 C3 C4 54.0(4)
C2 N3 C3 C4 -127.3(3)
C1 N3 C3 C8 -127.1(3)
C2 N3 C3 C8 51.6(3)
C8 C3 C4 C5 0.9(4)
N3 C3 C4 C5 179.7(3)
C3 C4 C5 C6 0.2(5)
C4 C5 C6 C7 -0.9(5)
C5 C6 C7 C8 0.5(6)
C4 C3 C8 C7 -1.2(5)
N3 C3 C8 C7 180.0(3)
C6 C7 C8 C3 0.5(6)
N1 N2 C9 O1 163.8(2)
C2 N2 C9 O1 22.4(3)
N1 N2 C9 C10 -18.8(3)
C2 N2 C9 C10 -160.3(2)
C11 N4 C10 C9 -94.7(3)
N5 N4 C10 C9 78.9(3)
O1 C9 C10 N4 10.1(3)
N2 C9 C10 N4 -167.2(2)
C12 N6 C11 N4 -0.6(3)
N5 N4 C11 N6 0.5(3)
C10 N4 C11 N6 174.5(3)
N4 N5 C12 N6 -0.3(4)
C11 N6 C12 N5 0.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128768
