##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2013-04-08
_journal_date_accepted     2013-04-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      5
_journal_page_first     o697
_journal_page_last     o697
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813009501
_journal_coeditor_code     HG5308
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
Edward.Tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
4-Benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mona M. Al-Shehri' .
;
Department of Pharmaceutical Chemistry, College of Pharmacy,
King Saud University, Riyadh 11451, Saudi Arabia
;
    'Ali A. El-Emam'
;
Additional correspondence author, e-mail: elemam5@hotmail.com.
;
;
Department of Pharmaceutical Chemistry, College of Pharmacy,
King Saud University, Riyadh 11451, Saudi Arabia
;
    'Nasser R. El-Brollosy' .
;
Department of Pharmaceutical Chemistry, College of Pharmacy,
King Saud University, Riyadh 11451, Saudi Arabia
;
    'Ng, Seik Weng' .
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
     Chemistry Department
     Faculty of Science
     King Abdulaziz University
     PO Box 80203 Jeddah
     Saudi Arabia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H11 N3 S2'
_chemical_formula_sum     'C13 H11 N3 S2'
_chemical_formula_iupac     'C13 H11 N3 S2'
_chemical_formula_weight     273.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     13.422(2)
_cell_length_b     6.1670(7)
_cell_length_c     16.596(2)
_cell_angle_alpha     90.00
_cell_angle_beta     111.972(15)
_cell_angle_gamma     90.00
_cell_volume     1273.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1615
_cell_measurement_theta_min     3.0308
_cell_measurement_theta_max     27.4975
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.425
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     0.402
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2011)'
_exptl_absorpt_correction_T_min     0.80612
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                  'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     6460
_diffrn_reflns_av_R_equivalents     0.0358
_diffrn_reflns_av_sigmaI/netI     0.0509
_diffrn_reflns_theta_min     3.27
_diffrn_reflns_theta_max     27.56
_diffrn_reflns_theta_full     27.56
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2937
_reflns_number_gt     2088
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0720
_refine_ls_R_factor_gt     0.0446
_refine_ls_wR_factor_gt     0.0944
_refine_ls_wR_factor_ref     0.1086
_refine_ls_goodness_of_fit_ref     1.023
_refine_ls_restrained_S_all     1.023
_refine_ls_number_reflns     2937
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0415P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.240
_refine_diff_density_min     -0.272
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.21756(5) 0.78528(13) 0.30574(4) 0.0548(2) Uani d . 1 1 . .
    S S2 0.47823(5) 0.12218(10) 0.62298(3) 0.03891(18) Uani d . 1 1 . .
    N N1 0.34574(15) 0.4060(3) 0.39839(11) 0.0395(5) Uani d . 1 1 . .
    N N2 0.40554(15) 0.2515(3) 0.45408(12) 0.0383(5) Uani d D 1 1 . .
    H H2 0.4302(18) 0.138(3) 0.4349(15) 0.052(8) Uiso d D 1 1 . .
    N N3 0.35676(13) 0.4651(3) 0.53331(10) 0.0304(4) Uani d . 1 1 . .
    C C1 0.14130(18) 0.9997(4) 0.31144(16) 0.0475(6) Uani d . 1 1 . .
    H H1 0.1054 1.0904 0.2648 0.057 Uiso calc R 1 1 . .
    C C2 0.1387(2) 1.0233(4) 0.39097(16) 0.0492(6) Uani d . 1 1 . .
    H H2A 0.1008 1.1330 0.4054 0.059 Uiso calc R 1 1 . .
    C C3 0.19944(19) 0.8647(4) 0.45051(14) 0.0426(6) Uani d . 1 1 . .
    H H3 0.2054 0.8574 0.5081 0.051 Uiso calc R 1 1 . .
    C C4 0.24840(16) 0.7233(4) 0.41373(13) 0.0346(5) Uani d . 1 1 . .
    C C5 0.31583(17) 0.5357(4) 0.44809(13) 0.0323(5) Uani d . 1 1 . .
    C C6 0.41379(16) 0.2783(3) 0.53621(13) 0.0315(5) Uani d . 1 1 . .
    C C7 0.34971(17) 0.5686(4) 0.61041(13) 0.0344(5) Uani d . 1 1 . .
    H H7A 0.3586 0.7238 0.6065 0.041 Uiso calc R 1 1 . .
    H H7B 0.4085 0.5168 0.6614 0.041 Uiso calc R 1 1 . .
    C C8 0.24552(17) 0.5271(4) 0.62246(12) 0.0344(5) Uani d . 1 1 . .
    C C9 0.1871(2) 0.3419(5) 0.59316(17) 0.0534(7) Uani d . 1 1 . .
    H H9 0.2110 0.2391 0.5635 0.064 Uiso calc R 1 1 . .
    C C10 0.0931(2) 0.3049(5) 0.6069(2) 0.0708(9) Uani d . 1 1 . .
    H H10 0.0540 0.1787 0.5863 0.085 Uiso calc R 1 1 . .
    C C11 0.0579(2) 0.4550(6) 0.65120(19) 0.0665(8) Uani d . 1 1 . .
    H H11 -0.0056 0.4316 0.6602 0.080 Uiso calc R 1 1 . .
    C C12 0.1160(2) 0.6383(5) 0.68195(17) 0.0595(8) Uani d . 1 1 . .
    H H12 0.0928 0.7387 0.7129 0.071 Uiso calc R 1 1 . .
    C C13 0.2092(2) 0.6763(4) 0.66753(15) 0.0474(6) Uani d . 1 1 . .
    H H13 0.2479 0.8029 0.6882 0.057 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0569(4) 0.0694(5) 0.0403(3) 0.0206(4) 0.0206(3) 0.0166(3)
    S2 0.0448(3) 0.0349(3) 0.0365(3) 0.0064(3) 0.0146(2) 0.0030(3)
    N1 0.0467(11) 0.0384(11) 0.0365(10) 0.0075(9) 0.0190(8) 0.0045(9)
    N2 0.0453(11) 0.0369(11) 0.0369(10) 0.0088(9) 0.0204(9) 0.0021(9)
    N3 0.0335(9) 0.0279(9) 0.0318(9) 0.0017(8) 0.0145(7) -0.0002(8)
    C1 0.0385(13) 0.0476(15) 0.0501(14) 0.0047(12) 0.0095(10) 0.0177(12)
    C2 0.0478(14) 0.0404(14) 0.0561(15) 0.0098(12) 0.0155(12) 0.0040(12)
    C3 0.0500(14) 0.0378(13) 0.0386(12) 0.0104(12) 0.0148(10) 0.0046(11)
    C4 0.0328(11) 0.0346(12) 0.0355(11) -0.0007(10) 0.0117(9) 0.0036(10)
    C5 0.0345(11) 0.0308(11) 0.0313(10) -0.0024(10) 0.0120(9) 0.0009(10)
    C6 0.0309(11) 0.0301(11) 0.0355(11) -0.0029(9) 0.0148(9) -0.0015(9)
    C7 0.0371(12) 0.0337(12) 0.0314(10) 0.0001(10) 0.0116(9) -0.0031(9)
    C8 0.0371(12) 0.0363(12) 0.0307(10) 0.0035(10) 0.0137(9) 0.0008(10)
    C9 0.0547(16) 0.0503(16) 0.0651(16) -0.0097(13) 0.0339(13) -0.0164(13)
    C10 0.0595(18) 0.073(2) 0.092(2) -0.0239(17) 0.0418(17) -0.0182(19)
    C11 0.0493(16) 0.089(2) 0.0722(18) 0.0006(17) 0.0350(14) 0.0030(18)
    C12 0.0588(17) 0.073(2) 0.0550(15) 0.0159(16) 0.0313(13) -0.0069(15)
    C13 0.0531(15) 0.0455(15) 0.0458(13) 0.0023(12) 0.0211(11) -0.0120(12)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 . 1.696(3) ?
    S1 C4 . 1.725(2) ?
    S2 C6 . 1.678(2) ?
    N1 C5 . 1.315(3) ?
    N1 N2 . 1.361(3) ?
    N2 C6 . 1.336(3) ?
    N2 H2 . 0.881(10) ?
    N3 C6 . 1.374(3) ?
    N3 C5 . 1.382(2) ?
    N3 C7 . 1.464(2) ?
    C1 C2 . 1.341(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.412(3) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.366(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.448(3) ?
    C7 C8 . 1.507(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.368(3) ?
    C8 C13 . 1.384(3) ?
    C9 C10 . 1.382(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.372(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.359(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.379(4) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 S1 C4 . . 91.71(11) ?
    C5 N1 N2 . . 103.94(17) ?
    C6 N2 N1 . . 114.13(18) ?
    C6 N2 H2 . . 124.6(16) ?
    N1 N2 H2 . . 121.0(16) ?
    C6 N3 C5 . . 107.63(16) ?
    C6 N3 C7 . . 123.51(17) ?
    C5 N3 C7 . . 128.77(18) ?
    C2 C1 S1 . . 112.20(18) ?
    C2 C1 H1 . . 123.9 ?
    S1 C1 H1 . . 123.9 ?
    C1 C2 C3 . . 113.1(2) ?
    C1 C2 H2A . . 123.4 ?
    C3 C2 H2A . . 123.4 ?
    C4 C3 C2 . . 112.2(2) ?
    C4 C3 H3 . . 123.9 ?
    C2 C3 H3 . . 123.9 ?
    C3 C4 C5 . . 131.97(19) ?
    C3 C4 S1 . . 110.76(16) ?
    C5 C4 S1 . . 117.24(16) ?
    N1 C5 N3 . . 110.66(19) ?
    N1 C5 C4 . . 122.11(18) ?
    N3 C5 C4 . . 127.23(19) ?
    N2 C6 N3 . . 103.62(17) ?
    N2 C6 S2 . . 128.59(17) ?
    N3 C6 S2 . . 127.78(15) ?
    N3 C7 C8 . . 114.11(17) ?
    N3 C7 H7A . . 108.7 ?
    C8 C7 H7A . . 108.7 ?
    N3 C7 H7B . . 108.7 ?
    C8 C7 H7B . . 108.7 ?
    H7A C7 H7B . . 107.6 ?
    C9 C8 C13 . . 118.4(2) ?
    C9 C8 C7 . . 122.1(2) ?
    C13 C8 C7 . . 119.4(2) ?
    C8 C9 C10 . . 121.1(3) ?
    C8 C9 H9 . . 119.5 ?
    C10 C9 H9 . . 119.5 ?
    C11 C10 C9 . . 119.7(3) ?
    C11 C10 H10 . . 120.1 ?
    C9 C10 H10 . . 120.1 ?
    C12 C11 C10 . . 119.9(3) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    C11 C12 C13 . . 120.4(3) ?
    C11 C12 H12 . . 119.8 ?
    C13 C12 H12 . . 119.8 ?
    C12 C13 C8 . . 120.4(3) ?
    C12 C13 H13 . . 119.8 ?
    C8 C13 H13 . . 119.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 N2 C6 . . . . 0.3(3) ?
    C4 S1 C1 C2 . . . . -0.2(2) ?
    S1 C1 C2 C3 . . . . -0.2(3) ?
    C1 C2 C3 C4 . . . . 0.7(3) ?
    C2 C3 C4 C5 . . . . -178.7(2) ?
    C2 C3 C4 S1 . . . . -0.8(3) ?
    C1 S1 C4 C3 . . . . 0.61(19) ?
    C1 S1 C4 C5 . . . . 178.87(18) ?
    N2 N1 C5 N3 . . . . 0.5(2) ?
    N2 N1 C5 C4 . . . . -179.08(19) ?
    C6 N3 C5 N1 . . . . -1.2(2) ?
    C7 N3 C5 N1 . . . . 175.28(19) ?
    C6 N3 C5 C4 . . . . 178.4(2) ?
    C7 N3 C5 C4 . . . . -5.1(3) ?
    C3 C4 C5 N1 . . . . 172.4(2) ?
    S1 C4 C5 N1 . . . . -5.4(3) ?
    C3 C4 C5 N3 . . . . -7.2(4) ?
    S1 C4 C5 N3 . . . . 175.03(17) ?
    N1 N2 C6 N3 . . . . -1.0(2) ?
    N1 N2 C6 S2 . . . . 178.98(16) ?
    C5 N3 C6 N2 . . . . 1.3(2) ?
    C7 N3 C6 N2 . . . . -175.41(18) ?
    C5 N3 C6 S2 . . . . -178.73(16) ?
    C7 N3 C6 S2 . . . . 4.6(3) ?
    C6 N3 C7 C8 . . . . -102.1(2) ?
    C5 N3 C7 C8 . . . . 81.9(3) ?
    N3 C7 C8 C9 . . . . 29.0(3) ?
    N3 C7 C8 C13 . . . . -153.6(2) ?
    C13 C8 C9 C10 . . . . 0.9(4) ?
    C7 C8 C9 C10 . . . . 178.3(2) ?
    C8 C9 C10 C11 . . . . -0.5(5) ?
    C9 C10 C11 C12 . . . . -0.6(5) ?
    C10 C11 C12 C13 . . . . 1.2(5) ?
    C11 C12 C13 C8 . . . . -0.8(4) ?
    C9 C8 C13 C12 . . . . -0.3(3) ?
    C7 C8 C13 C12 . . . . -177.8(2) ?
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
    N2 H2 S2 3_656 0.881(10) 2.429(11) 3.297(2) 169(2)
    C13 H13 Cg1 2_556 0.93 2.94 3.636(3) 133
