#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/86/2008605.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_2008605
loop_
_publ_author_name
'Puviarasan, K.'
'Govindasamy, L.'
'Shanmuga Sundara Raj, S.'
'Velmurugan, D.'
'Jayanthi, G.'
'Hoong-Kun Fun'
_publ_section_title
;
 5-(2-Chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4-triazole-3-thione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              951
_journal_page_last               953
_journal_paper_doi               10.1107/S0108270199002796
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C14 H10 Cl N3 S'
_chemical_formula_weight         287.76
_chemical_name_systematic
;
5-(2-Chlorophenyl)-4-phenyl-4H-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           SHELXL97
_cell_angle_alpha                97.5560(10)
_cell_angle_beta                 104.2980(10)
_cell_angle_gamma                95.4030(10)
_cell_formula_units_Z            2
_cell_length_a                   6.96750(10)
_cell_length_b                   9.5232(2)
_cell_length_c                   11.0979(3)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.51
_cell_measurement_theta_min      5.38
_cell_volume                     701.20(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983; 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Siemens (model?)'
_diffrn_measurement_method       θ/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  0.016
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4570
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.448
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0489P)²+0.2548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                2554
_reflns_number_total             3099
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1044.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.2548P] 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^)+(0.0489P)^2^+0.2548P] 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               2008605
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
H1N3 .110(4) .541(3) -.084(2) .064(7) Uiso d . 1 . . H
S1 .05936(8) .26944(5) .00820(5) .04514(15) Uani d . 1 . . S
Cl1 .16039(12) .16521(8) -.47746(6) .0836(2) Uani d . 1 . . Cl
N1 .2717(2) .28075(14) -.17007(13) .0352(3) Uani d . 1 . . N
N2 .2734(3) .50528(16) -.20297(17) .0496(4) Uani d . 1 . . N
N3 .1727(3) .47786(17) -.11479(17) .0477(4) Uani d . 1 . . N
C1 .1665(3) .34379(18) -.09211(16) .0372(4) Uani d . 1 . . C
C2 .3329(3) .38390(18) -.23453(17) .0394(4) Uani d . 1 . . C
C3 .3251(3) .13828(17) -.17252(15) .0347(4) Uani d . 1 . . C
C4 .5247(3) .12104(19) -.14211(17) .0413(4) Uani d . 1 . . C
H4 .6225 .2002 -.1209 .050 Uiso calc R 1 . . H
C5 .5777(3) -.0156(2) -.1436(2) .0519(5) Uani d . 1 . . C
H5 .7119 -.0285 -.1240 .062 Uiso calc R 1 . . H
C6 .4332(4) -.1317(2) -.1738(2) .0548(5) Uani d . 1 . . C
H6 .4699 -.2230 -.1737 .066 Uiso calc R 1 . . H
C7 .2341(4) -.1142(2) -.20440(19) .0538(5) Uani d . 1 . . C
H7 .1370 -.1938 -.2253 .065 Uiso calc R 1 . . H
C8 .1775(3) .02206(19) -.20415(18) .0450(4) Uani d . 1 . . C
H8 .0432 .0347 -.2248 .054 Uiso calc R 1 . . H
C9 .4562(3) .36328(19) -.32456(17) .0417(4) Uani d . 1 . . C
C10 .6382(3) .4484(3) -.2994(2) .0577(5) Uani d . 1 . . C
H10 .6815 .5147 -.2258 .069 Uiso calc R 1 . . H
C11 .7569(4) .4359(4) -.3829(3) .0781(8) Uani d . 1 . . C
H11 .8779 .4947 -.3660 .094 Uiso calc R 1 . . H
C12 .6949(5) .3364(4) -.4905(3) .0842(9) Uani d . 1 . . C
H12 .7754 .3271 -.5459 .101 Uiso calc R 1 . . H
C13 .5155(5) .2506(3) -.5172(2) .0769(8) Uani d . 1 . . C
H13 .4752 .1826 -.5898 .092 Uiso calc R 1 . . H
C14 .3946(3) .2656(2) -.43563(19) .0526(5) Uani d . 1 . . C
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
C1 N1 C2 107.49(14) yes
C1 N1 C3 125.50(14) yes
C2 N1 C3 126.70(13) yes
C2 N2 N3 103.68(14) yes
C1 N3 N2 114.24(14) yes
C1 N3 H1N3 124.5(17) ?
N2 N3 H1N3 120.9(17) ?
N3 C1 N1 103.28(15) yes
N3 C1 S1 128.53(13) yes
N1 C1 S1 128.19(13) yes
N2 C2 N1 111.31(15) yes
N2 C2 C9 123.22(16) yes
N1 C2 C9 125.43(15) yes
C4 C3 C8 121.31(16) ?
C4 C3 N1 118.69(15) yes
C8 C3 N1 120.00(16) yes
C3 C4 C5 119.16(18) ?
C3 C4 H4 120.4 ?
C5 C4 H4 120.4 ?
C6 C5 C4 120.2(2) ?
C6 C5 H5 119.9 ?
C4 C5 H5 119.9 ?
C5 C6 C7 120.54(18) ?
C5 C6 H6 119.7 ?
C7 C6 H6 119.7 ?
C6 C7 C8 120.20(19) ?
C6 C7 H7 119.9 ?
C8 C7 H7 119.9 ?
C3 C8 C7 118.59(19) ?
C3 C8 H8 120.7 ?
C7 C8 H8 120.7 ?
C10 C9 C14 118.46(18) ?
C10 C9 C2 118.57(17) ?
C14 C9 C2 122.93(18) ?
C9 C10 C11 120.7(2) ?
C9 C10 H10 119.6 ?
C11 C10 H10 119.6 ?
C12 C11 C10 119.7(3) ?
C12 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
C11 C12 C13 120.6(2) ?
C11 C12 H12 119.7 ?
C13 C12 H12 119.7 ?
C12 C13 C14 119.8(2) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
C13 C14 C9 120.7(2) ?
C13 C14 Cl1 118.77(19) yes
C9 C14 Cl1 120.47(16) yes
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
S1 C1 . 1.6781(18) yes
Cl1 C14 . 1.734(2) yes
N1 C1 . 1.381(2) yes
N1 C2 . 1.384(2) yes
N1 C3 . 1.439(2) yes
N2 C2 . 1.299(2) yes
N2 N3 . 1.374(2) yes
N3 C1 . 1.332(2) yes
N3 H1N3 . .86(3) ?
C2 C9 . 1.476(2) yes
C3 C4 . 1.379(3) ?
C3 C8 . 1.383(2) ?
C4 C5 . 1.384(3) ?
C4 H4 . .9300 ?
C5 C6 . 1.369(3) ?
C5 H5 . .9300 ?
C6 C7 . 1.376(3) ?
C6 H6 . .9300 ?
C7 C8 . 1.391(3) ?
C7 H7 . .9300 ?
C8 H8 . .9300 ?
C9 C10 . 1.384(3) ?
C9 C14 . 1.390(3) ?
C10 C11 . 1.387(3) ?
C10 H10 . .9300 ?
C11 C12 . 1.372(4) ?
C11 H11 . .9300 ?
C12 C13 . 1.371(4) ?
C12 H12 . .9300 ?
C13 C14 . 1.384(3) ?
C13 H13 . .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 N2 N3 C1 -0.7(2)
N2 N3 C1 N1 0.6(2)
N2 N3 C1 S1 179.86(15)
C2 N1 C1 N3 -0.20(19)
C3 N1 C1 N3 173.70(16)
C2 N1 C1 S1 -179.50(14)
C3 N1 C1 S1 -5.6(3)
N3 N2 C2 N1 0.5(2)
N3 N2 C2 C9 -177.44(18)
C1 N1 C2 N2 -0.2(2)
C3 N1 C2 N2 -174.03(17)
C1 N1 C2 C9 177.70(17)
C3 N1 C2 C9 3.9(3)
C1 N1 C3 C4 -117.59(19)
C2 N1 C3 C4 55.1(2)
C1 N1 C3 C8 62.0(2)
C2 N1 C3 C8 -125.26(19)
C8 C3 C4 C5 0.1(3)
N1 C3 C4 C5 179.70(16)
C3 C4 C5 C6 -0.6(3)
C4 C5 C6 C7 0.7(3)
C5 C6 C7 C8 -0.4(3)
C4 C3 C8 C7 0.2(3)
N1 C3 C8 C7 -179.36(16)
C6 C7 C8 C3 -0.1(3)
N2 C2 C9 C10 57.4(3)
N1 C2 C9 C10 -120.3(2)
N2 C2 C9 C14 -120.4(2)
N1 C2 C9 C14 61.9(3)
C14 C9 C10 C11 -0.3(3)
C2 C9 C10 C11 -178.2(2)
C9 C10 C11 C12 -1.1(4)
C10 C11 C12 C13 0.9(5)
C11 C12 C13 C14 0.8(5)
C12 C13 C14 C9 -2.3(4)
C12 C13 C14 Cl1 175.2(2)
C10 C9 C14 C13 2.0(3)
C2 C9 C14 C13 179.8(2)
C10 C9 C14 Cl1 -175.38(17)
C2 C9 C14 Cl1 2.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 634022
