#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235168.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_2235168
loop_
_publ_author_name
'Jing, Bi'
'Du, Yuao-Chao'
'Zhu, Ai-Xin'
_publ_section_title
;
 3-Ethyl-1H-1,2,4-triazole-5(4H)-thione
;
_journal_coeditor_code           NC2279
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1802
_journal_paper_doi               10.1107/S1600536812021927
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C4 H7 N3 S'
_chemical_formula_moiety         'C4 H7 N3 S'
_chemical_formula_sum            'C4 H7 N3 S'
_chemical_formula_weight         129.19
_chemical_name_systematic
;
3-Ethyl-1H-1,2,4-triazole-5(4H)-thione
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 90.17(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0922(10)
_cell_length_b                   6.7526(14)
_cell_length_c                   8.6578(17)
_cell_measurement_temperature    293(2)
_cell_volume                     297.70(10)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2467
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         3.83
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_correction_T_min  0.8962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             136
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.4796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                590
_reflns_number_total             637
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nc2279.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2235168
_cod_database_fobs_code          2235168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
S S1 0.45391(12) 0.2500 0.74979(7) 0.03824(18) Uani d S 1 2
N N1 0.0168(4) 0.2500 0.5691(3) 0.0384(6) Uani d S 1 2
H H1D -0.0890 0.2500 0.6464 0.046 Uiso calc SR 1 2
N N2 -0.0665(4) 0.2500 0.4165(2) 0.0344(5) Uani d S 1 2
N N3 0.3624(4) 0.2500 0.4359(2) 0.0347(5) Uani d S 1 2
H H3A 0.5244 0.2500 0.4082 0.042 Uiso calc SR 1 2
C C1 -0.0885(5) 0.2500 0.0845(3) 0.0447(8) Uani d S 1 2
H H1A -0.0616 0.2500 -0.0252 0.067 Uiso calc SR 1 2
H H1B -0.1855 0.3661 0.1135 0.067 Uiso calc PR 0.50 1
H H1C -0.1855 0.1339 0.1135 0.067 Uiso calc PR 0.50 1
C C2 0.1729(5) 0.2500 0.1657(3) 0.0377(7) Uani d S 1 2
H H2A 0.2710 0.1340 0.1336 0.045 Uiso calc PR 0.50 1
H H2B 0.2710 0.3660 0.1336 0.045 Uiso calc PR 0.50 1
C C3 0.1532(5) 0.2500 0.3376(3) 0.0311(6) Uani d S 1 2
C C4 0.2769(5) 0.2500 0.5841(3) 0.0345(6) Uani d S 1 2
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 0.0270(3) 0.0578(4) 0.0299(3) 0.000 -0.0018(2) 0.000
N1 0.0287(10) 0.0526(14) 0.0338(11) 0.000 0.0008(9) 0.000
N2 0.0258(9) 0.0435(12) 0.0339(11) 0.000 -0.0006(8) 0.000
N3 0.0204(9) 0.0486(13) 0.0349(11) 0.000 0.0017(8) 0.000
C1 0.0332(13) 0.0639(19) 0.0368(14) 0.000 -0.0086(11) 0.000
C2 0.0276(11) 0.0535(16) 0.0321(12) 0.000 -0.0014(10) 0.000
C3 0.0229(10) 0.0334(13) 0.0368(12) 0.000 -0.0025(9) 0.000
C4 0.0274(11) 0.0368(13) 0.0393(13) 0.000 0.0003(10) 0.000
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
C4 N1 N2 113.2(2)
C4 N1 H1D 123.4
N2 N1 H1D 123.4
C3 N2 N1 103.7(2)
C4 N3 C3 109.8(2)
C4 N3 H3A 125.1
C3 N3 H3A 125.1
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C1 113.8(2)
C3 C2 H2A 108.8
C1 C2 H2A 108.8
C3 C2 H2B 108.8
C1 C2 H2B 108.8
H2A C2 H2B 107.7
N2 C3 N3 109.9(2)
N2 C3 C2 125.4(2)
N3 C3 C2 124.6(2)
N1 C4 N3 103.3(2)
N1 C4 S1 127.6(2)
N3 C4 S1 129.07(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.692(3)
N1 C4 1.330(3)
N1 N2 1.386(3)
N1 H1D 0.8600
N2 C3 1.312(3)
N3 C4 1.356(3)
N3 C3 1.362(3)
N3 H3A 0.8600
C1 C2 1.504(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.492(4)
C2 H2A 0.9700
C2 H2B 0.9700
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
_geom_hbond_publ_flag
N1 H1D S1 1_455 0.86 2.50 3.270(2) 150.0 y
N3 H3A N2 1_655 0.86 2.08 2.914(3) 161.8 y
