##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-07-30
_journal_date_accepted     2010-07-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2224
_journal_page_last     o2224
_journal_paper_category     QO
_journal_coeditor_code     XU5008
_publ_contact_author
;
     Dr. M. Jamil Maah
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     mjamil@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
5-Ethyl-5-methyl-4-phenyl-5H-1,2,4-triazol-3(4H)-thione
;
loop_
    _publ_author_name
    _publ_author_address
    'Tan, Kong Wai'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Maah, M. Jamil'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-Ethyl-5-methyl-4-phenyl-5H-1,2,4-triazol-3(4H)-thione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H13 N3 S'
_chemical_formula_sum     'C11 H13 N3 S'
_chemical_formula_iupac     'C11 H13 N3 S'
_chemical_formula_weight     219.30
_chemical_melting_point     ?
_symmetry_cell_setting     tetragonal
_symmetry_space_group_name_H-M     'P -4 21 c'
_symmetry_space_group_name_Hall     'P -4 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'y, -x, -z'
    '-y, x, -z'
    '-x+1/2, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z+1/2'
    '-y+1/2, -x+1/2, z+1/2'
    'y+1/2, x+1/2, z+1/2'
_cell_length_a     17.962(4)
_cell_length_b     17.962
_cell_length_c     6.9992(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2258.2(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     926
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     18.5
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Orange
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.290
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     928
_exptl_absorpt_coefficient_mu     0.257
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9269
_exptl_absorpt_correction_T_max     0.9873
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10418
_diffrn_reflns_av_R_equivalents     0.0865
_diffrn_reflns_av_sigmaI/netI     0.0659
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     5
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     1987
_reflns_number_gt     1546
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0893
_refine_ls_R_factor_gt     0.0654
_refine_ls_wR_factor_gt     0.1690
_refine_ls_wR_factor_ref     0.1855
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     1987
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0992P)²+1.8759P] 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     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.689
_refine_diff_density_min     -0.307
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 837 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.2(2)
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     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.47452(8) 0.23341(7) 1.2411(2) 0.0351(4) Uani d . 1 . .
    N N1 0.4463(3) 0.2810(3) 0.8841(6) 0.0351(11) Uani d . 1 . .
    N N2 0.4094(3) 0.3589(3) 1.1143(7) 0.0531(15) Uani d . 1 . .
    N N3 0.3934(3) 0.3924(3) 0.9623(8) 0.0511(14) Uani d . 1 . .
    C C1 0.4778(3) 0.2198(2) 0.7806(6) 0.0237(10) Uani d . 1 . .
    C C2 0.5518(3) 0.2275(3) 0.7230(8) 0.0353(13) Uani d . 1 . .
    H H2 0.5801 0.2706 0.7530 0.042 Uiso calc R 1 . .
    C C3 0.5823(3) 0.1677(3) 0.6175(9) 0.0441(15) Uani d . 1 . .
    H H3 0.6323 0.1704 0.5738 0.053 Uiso calc R 1 . .
    C C4 0.5409(4) 0.1065(3) 0.5785(8) 0.0480(17) Uani d . 1 . .
    H H4 0.5623 0.0671 0.5066 0.058 Uiso calc R 1 . .
    C C5 0.4687(4) 0.1003(3) 0.6404(8) 0.0435(15) Uani d . 1 . .
    H H5 0.4406 0.0568 0.6136 0.052 Uiso calc R 1 . .
    C C6 0.4381(3) 0.1576(3) 0.7413(9) 0.0351(12) Uani d . 1 . .
    H H6 0.3881 0.1537 0.7846 0.042 Uiso calc R 1 . .
    C C7 0.4431(3) 0.2869(3) 1.0741(7) 0.0371(14) Uani d . 1 . .
    C C8 0.4127(3) 0.3477(3) 0.7940(8) 0.0398(14) Uani d . 1 . .
    C C9 0.4652(4) 0.3911(3) 0.6695(9) 0.0525(17) Uani d . 1 . .
    H H9A 0.5098 0.4041 0.7429 0.079 Uiso calc R 1 . .
    H H9B 0.4407 0.4367 0.6254 0.079 Uiso calc R 1 . .
    H H9C 0.4794 0.3607 0.5590 0.079 Uiso calc R 1 . .
    C C10 0.3418(3) 0.3257(4) 0.6851(9) 0.0528(18) Uani d . 1 . .
    H H10A 0.3210 0.3707 0.6231 0.063 Uiso calc R 1 . .
    H H10B 0.3554 0.2902 0.5828 0.063 Uiso calc R 1 . .
    C C11 0.2824(4) 0.2911(5) 0.8070(11) 0.073(2) Uani d . 1 . .
    H H11A 0.2391 0.2789 0.7276 0.109 Uiso calc R 1 . .
    H H11B 0.2675 0.3262 0.9072 0.109 Uiso calc R 1 . .
    H H11C 0.3017 0.2455 0.8659 0.109 Uiso calc R 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 0.0531(8) 0.0347(6) 0.0174(6) -0.0009(6) -0.0038(7) 0.0016(7)
    N1 0.051(3) 0.033(2) 0.021(2) 0.014(2) -0.004(2) -0.001(2)
    N2 0.069(4) 0.058(3) 0.033(3) 0.025(3) -0.008(3) -0.007(3)
    N3 0.058(3) 0.048(3) 0.047(3) 0.010(3) -0.015(3) -0.009(3)
    C1 0.035(2) 0.024(2) 0.012(2) 0.0085(19) -0.006(2) 0.000(2)
    C2 0.042(3) 0.031(3) 0.032(3) -0.009(2) -0.009(3) 0.000(3)
    C3 0.036(3) 0.055(4) 0.041(4) 0.012(3) 0.015(3) 0.008(3)
    C4 0.088(5) 0.034(3) 0.022(3) 0.023(3) 0.001(3) 0.002(3)
    C5 0.072(4) 0.029(3) 0.029(3) -0.006(3) -0.010(3) -0.003(2)
    C6 0.038(3) 0.038(3) 0.030(3) -0.001(2) 0.006(3) 0.001(3)
    C7 0.053(4) 0.042(3) 0.016(3) 0.019(2) -0.002(2) -0.008(2)
    C8 0.044(3) 0.039(3) 0.037(4) 0.006(2) -0.001(3) -0.001(3)
    C9 0.059(4) 0.048(3) 0.051(4) -0.006(3) -0.019(3) 0.021(3)
    C10 0.047(4) 0.066(4) 0.046(4) 0.004(3) -0.003(3) -0.009(3)
    C11 0.045(4) 0.101(6) 0.072(6) -0.004(4) -0.009(4) -0.012(5)
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 C7 . 1.614(5) ?
    N1 C7 . 1.335(7) ?
    N1 C1 . 1.433(6) ?
    N1 C8 . 1.483(7) ?
    N2 N3 . 1.255(7) ?
    N2 C7 . 1.456(7) ?
    N3 C8 . 1.466(8) ?
    C1 C6 . 1.355(7) ?
    C1 C2 . 1.396(7) ?
    C2 C3 . 1.415(8) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.355(9) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.372(9) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.364(8) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C8 C9 . 1.502(8) ?
    C8 C10 . 1.535(8) ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 C11 . 1.502(10) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
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
    C7 N1 C1 . . 125.5(5) ?
    C7 N1 C8 . . 110.0(5) ?
    C1 N1 C8 . . 124.5(4) ?
    N3 N2 C7 . . 110.9(5) ?
    N2 N3 C8 . . 111.4(4) ?
    C6 C1 C2 . . 121.7(4) ?
    C6 C1 N1 . . 121.8(5) ?
    C2 C1 N1 . . 116.5(4) ?
    C1 C2 C3 . . 116.4(5) ?
    C1 C2 H2 . . 121.8 ?
    C3 C2 H2 . . 121.8 ?
    C4 C3 C2 . . 120.6(5) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 121.4(5) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C6 C5 C4 . . 119.0(5) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    C1 C6 C5 . . 121.0(5) ?
    C1 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    N1 C7 N2 . . 106.3(5) ?
    N1 C7 S1 . . 131.2(5) ?
    N2 C7 S1 . . 122.3(4) ?
    N3 C8 N1 . . 101.3(4) ?
    N3 C8 C9 . . 109.3(5) ?
    N1 C8 C9 . . 114.2(5) ?
    N3 C8 C10 . . 110.1(5) ?
    N1 C8 C10 . . 109.9(5) ?
    C9 C8 C10 . . 111.5(5) ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C11 C10 C8 . . 114.4(6) ?
    C11 C10 H10A . . 108.7 ?
    C8 C10 H10A . . 108.7 ?
    C11 C10 H10B . . 108.7 ?
    C8 C10 H10B . . 108.7 ?
    H10A C10 H10B . . 107.6 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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
    C7 N2 N3 C8 . . . . 0.9(7) ?
    C7 N1 C1 C6 . . . . 85.0(7) ?
    C8 N1 C1 C6 . . . . -95.6(6) ?
    C7 N1 C1 C2 . . . . -94.8(7) ?
    C8 N1 C1 C2 . . . . 84.7(6) ?
    C6 C1 C2 C3 . . . . 1.5(7) ?
    N1 C1 C2 C3 . . . . -178.8(4) ?
    C1 C2 C3 C4 . . . . -0.7(8) ?
    C2 C3 C4 C5 . . . . -0.5(9) ?
    C3 C4 C5 C6 . . . . 0.9(9) ?
    C2 C1 C6 C5 . . . . -1.1(8) ?
    N1 C1 C6 C5 . . . . 179.1(5) ?
    C4 C5 C6 C1 . . . . -0.1(9) ?
    C1 N1 C7 N2 . . . . 177.8(5) ?
    C8 N1 C7 N2 . . . . -1.8(7) ?
    C1 N1 C7 S1 . . . . 2.9(10) ?
    C8 N1 C7 S1 . . . . -176.6(5) ?
    N3 N2 C7 N1 . . . . 0.5(7) ?
    N3 N2 C7 S1 . . . . 175.9(5) ?
    N2 N3 C8 N1 . . . . -1.9(6) ?
    N2 N3 C8 C9 . . . . -122.7(6) ?
    N2 N3 C8 C10 . . . . 114.5(6) ?
    C7 N1 C8 N3 . . . . 2.2(6) ?
    C1 N1 C8 N3 . . . . -177.3(5) ?
    C7 N1 C8 C9 . . . . 119.6(6) ?
    C1 N1 C8 C9 . . . . -60.0(7) ?
    C7 N1 C8 C10 . . . . -114.3(5) ?
    C1 N1 C8 C10 . . . . 66.2(7) ?
    N3 C8 C10 C11 . . . . -50.8(8) ?
    N1 C8 C10 C11 . . . . 60.0(7) ?
    C9 C8 C10 C11 . . . . -172.4(6) ?
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
    C9 H9A N2 4_657 0.98 2.56 3.519(9) 165
