#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/80/2228099.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228099
loop_
_publ_author_name
'Tan, Kong Wai'
'Maah, M. Jamil'
'Ng, Seik Weng'
_publ_section_title
;
 5-Ethyl-5-methyl-4-phenyl-5H-1,2,4-triazol-3(4H)-thione
;
_journal_coeditor_code           XU5008
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2224
_journal_paper_doi               10.1107/S1600536810030503
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 N3 S'
_chemical_formula_moiety         'C11 H13 N3 S'
_chemical_formula_sum            'C11 H13 N3 S'
_chemical_formula_weight         219.30
_chemical_name_systematic
;
5-Ethyl-5-methyl-4-phenyl-5H-1,2,4-triazol-3(4H)-thione
;
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.962(4)
_cell_length_b                   17.962
_cell_length_c                   6.9992(14)
_cell_measurement_reflns_used    926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.5
_cell_measurement_theta_min      2.5
_cell_volume                     2258.2(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0865
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10418
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.307
_refine_ls_abs_structure_details 'Flack (1983), 837 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0992P)²+1.8759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                1546
_reflns_number_total             1987
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5008.cif
_cod_data_source_block           I
_cod_original_cell_volume        2258.2(6)
_cod_database_code               2228099
_cod_database_fobs_code          2228099
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'
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_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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2987083
