#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/83/2008321.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_2008321
loop_
_publ_author_name
Kumaran,D.
Ponnuswamy,M.N.
Jayanthi,G.
'Ramakrishnan, V.T.'
'Chinnakali, K.'
'Fun, H.-K.'
_publ_section_title
;
 3-(2-Chlorophenyl)-4-phenyl-1,2,4-triazole-5-thione
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              581
_journal_page_last               582
_journal_paper_doi               10.1107/S0108270198013808
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C14 H10 Cl N3 S'
_chemical_formula_weight         287.76
_chemical_melting_point          241
_chemical_name_systematic
;
4-Phenyl 5-(2-chlorophenyl) 1,2,4-triazole-3-thione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                97.5950(10)
_cell_angle_beta                 104.2951(5)
_cell_angle_gamma                95.327(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9693(2)
_cell_length_b                   9.5268(3)
_cell_length_c                   11.1032(4)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.2
_cell_measurement_theta_min      2.66
_cell_volume                     702.04(4)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       '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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4631
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Column
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.043
_refine_ls_goodness_of_fit_obs   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_restrained_S_obs      1.054
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_obs          0.0478
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0532P)²+0.3068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1288
_refine_ls_wR_factor_obs         0.1126
_reflns_number_observed          2390
_reflns_number_total             3133
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            bm1285.cif
_cod_data_source_block           np10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.3068P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.3068P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2008321
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.16094(13) 0.16525(10) -0.47723(7) 0.0847(3) Uani d . 1 . Cl
S1 0.05926(9) 0.26959(6) 0.00810(6) 0.0465(2) Uani d . 1 . S
N1 0.2733(3) 0.5049(2) -0.2032(2) 0.0508(5) Uani d . 1 . N
N2 0.1729(3) 0.4780(2) -0.1145(2) 0.0489(5) Uani d . 1 . N
C3 0.1665(3) 0.3438(2) -0.0923(2) 0.0387(5) Uani d . 1 . C
N4 0.2719(2) 0.2809(2) -0.1701(2) 0.0361(4) Uani d . 1 . N
C5 0.3324(3) 0.3838(2) -0.2349(2) 0.0400(5) Uani d . 1 . C
C6 0.4565(3) 0.3631(2) -0.3243(2) 0.0424(5) Uani d . 1 . C
C7 0.6382(4) 0.4481(3) -0.2995(3) 0.0588(7) Uani d . 1 . C
C8 0.7569(5) 0.4358(4) -0.3830(3) 0.0791(9) Uani d . 1 . C
C9 0.6949(5) 0.3367(4) -0.4908(3) 0.0837(10) Uani d . 1 . C
C10 0.5159(6) 0.2507(4) -0.5173(3) 0.0769(9) Uani d . 1 . C
C11 0.3950(4) 0.2657(3) -0.4355(2) 0.0536(6) Uani d . 1 . C
C12 0.3248(3) 0.1381(2) -0.1726(2) 0.0357(4) Uani d . 1 . C
C13 0.1772(4) 0.0221(2) -0.2043(2) 0.0459(5) Uani d . 1 . C
C14 0.2341(5) -0.1137(2) -0.2046(2) 0.0541(6) Uani d . 1 . C
C15 0.4333(5) -0.1316(3) -0.1736(2) 0.0563(6) Uani d . 1 . C
C16 0.5781(4) -0.0155(3) -0.1439(2) 0.0527(6) Uani d . 1 . C
C17 0.5246(3) 0.1212(2) -0.1421(2) 0.0423(5) Uani d . 1 . C
H2 0.111(5) 0.538(3) -0.088(3) 0.071(9) Uiso d . 1 . H
H7 0.687(4) 0.519(3) -0.227(2) 0.050(7) Uiso d . 1 . H
H8 0.874(5) 0.496(4) -0.362(3) 0.089(11) Uiso d . 1 . H
H9 0.779(5) 0.321(4) -0.557(3) 0.100(11) Uiso d . 1 . H
H10 0.479(5) 0.180(4) -0.587(3) 0.093(11) Uiso d . 1 . H
H13 0.031(4) 0.042(3) -0.229(2) 0.058(7) Uiso d . 1 . H
H14 0.139(4) -0.192(3) -0.227(3) 0.065(8) Uiso d . 1 . H
H15 0.470(4) -0.224(3) -0.175(3) 0.072(9) Uiso d . 1 . H
H16 0.714(5) -0.029(4) -0.115(3) 0.086(10) Uiso d . 1 . H
H17 0.618(4) 0.201(3) -0.121(2) 0.046(7) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C5 N1 N2 103.8(2) y
C3 N2 N1 114.0(2) y
C3 N2 H2 125.(2) ?
N1 N2 H2 120.(2) ?
N2 C3 N4 103.4(2) y
N2 C3 S1 128.3(2) y
N4 C3 S1 128.3(2) y
C3 N4 C5 107.5(2) y
C3 N4 C12 125.4(2) y
C5 N4 C12 126.8(2) y
N1 C5 N4 111.3(2) y
N1 C5 C6 123.3(2) y
N4 C5 C6 125.4(2) y
C7 C6 C11 118.3(2) ?
C7 C6 C5 118.9(2) ?
C11 C6 C5 122.7(2) ?
C6 C7 C8 120.9(3) ?
C6 C7 H7 122.7(15) ?
C8 C7 H7 116.4(15) ?
C9 C8 C7 119.7(3) ?
C9 C8 H8 124.(2) ?
C7 C8 H8 117.(2) ?
C10 C9 C8 120.5(3) ?
C10 C9 H9 116.0(19) ?
C8 C9 H9 123.4(19) ?
C9 C10 C11 119.7(3) ?
C9 C10 H10 120.(2) ?
C11 C10 H10 120.(2) ?
C10 C11 C6 120.8(3) ?
C10 C11 Cl1 118.7(2) ?
C6 C11 Cl1 120.4(2) ?
C17 C12 C13 121.6(2) ?
C17 C12 N4 118.4(2) ?
C13 C12 N4 120.1(2) ?
C12 C13 C14 118.4(2) ?
C12 C13 H13 117.4(14) ?
C14 C13 H13 124.1(14) ?
C15 C14 C13 120.5(2) ?
C15 C14 H14 119.6(19) ?
C13 C14 H14 119.9(19) ?
C16 C15 C14 120.4(2) ?
C16 C15 H15 119.8(18) ?
C14 C15 H15 119.7(18) ?
C15 C16 C17 120.1(2) ?
C15 C16 H16 119.(2) ?
C17 C16 H16 120.(2) ?
C12 C17 C16 119.1(2) ?
C12 C17 H17 119.1(15) ?
C16 C17 H17 121.8(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C11 . 1.735(3) y
S1 C3 . 1.680(2) y
N1 C5 . 1.295(3) y
N1 N2 . 1.378(3) y
N2 C3 . 1.333(3) y
N2 H2 . 0.81(3) ?
C3 N4 . 1.379(3) y
N4 C5 . 1.384(3) y
N4 C12 . 1.441(2) y
C5 C6 . 1.475(3) y
C6 C7 . 1.383(3) ?
C6 C11 . 1.390(3) ?
C7 C8 . 1.387(4) ?
C7 H7 . 0.95(2) ?
C8 C9 . 1.372(5) ?
C8 H8 . 0.91(3) ?
C9 C10 . 1.371(5) ?
C9 H9 . 1.05(4) ?
C10 C11 . 1.386(4) ?
C10 H10 . 0.92(4) ?
C12 C17 . 1.379(3) ?
C12 C13 . 1.382(3) ?
C13 C14 . 1.388(3) ?
C13 H13 . 1.03(3) ?
C14 C15 . 1.378(4) ?
C14 H14 . 0.91(3) ?
C15 C16 . 1.371(4) ?
C15 H15 . 0.94(3) ?
C16 C17 . 1.387(3) ?
C16 H16 . 0.95(3) ?
C17 H17 . 0.92(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
_geom_torsion_publ_flag
C5 N1 N2 C3 -0.8(3) y
N1 N2 C3 N4 0.9(3) y
N1 N2 C3 S1 180.0(2) y
N2 C3 N4 C5 -0.6(2) y
S1 C3 N4 C5 -179.7(2) y
N2 C3 N4 C12 173.8(2) y
S1 C3 N4 C12 -5.3(3) y
N2 N1 C5 N4 0.4(3) y
N2 N1 C5 C6 -176.9(2) y
C3 N4 C5 N1 0.1(2) y
C12 N4 C5 N1 -174.1(2) y
C3 N4 C5 C6 177.3(2) y
C12 N4 C5 C6 3.0(3) y
N1 C5 C6 C7 56.8(3) ?
N4 C5 C6 C7 -120.1(2) ?
N1 C5 C6 C11 -120.4(3) ?
N4 C5 C6 C11 62.8(3) ?
C11 C6 C7 C8 -0.5(4) ?
C5 C6 C7 C8 -177.8(3) ?
C6 C7 C8 C9 -0.9(5) ?
C7 C8 C9 C10 0.6(6) ?
C8 C9 C10 C11 1.1(6) ?
C9 C10 C11 C6 -2.6(5) ?
C9 C10 C11 Cl1 175.1(3) ?
C7 C6 C11 C10 2.3(4) ?
C5 C6 C11 C10 179.4(3) ?
C7 C6 C11 Cl1 -175.4(2) ?
C5 C6 C11 Cl1 1.8(3) ?
C3 N4 C12 C17 -117.7(2) ?
C5 N4 C12 C17 55.6(3) ?
C3 N4 C12 C13 61.8(3) ?
C5 N4 C12 C13 -124.9(2) ?
C17 C12 C13 C14 0.1(3) ?
N4 C12 C13 C14 -179.4(2) ?
C12 C13 C14 C15 0.2(3) ?
C13 C14 C15 C16 -1.0(4) ?
C14 C15 C16 C17 1.5(4) ?
C13 C12 C17 C16 0.3(3) ?
N4 C12 C17 C16 179.9(2) ?
C15 C16 C17 C12 -1.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 634022
