#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/06/2220677.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_2220677
loop_
_publ_author_name
'Wujec, Monika'
'Mazur, Liliana'
'Rzaczyńska, Zofia'
_publ_section_title
;
 4-Ethyl-3-(2-thienylmethyl)-Δ²-1,2,4-triazoline-5-thione
;
_journal_coeditor_code           AT2696
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o274
_journal_paper_doi               10.1107/S1600536809000440
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H11 N3 S2'
_chemical_formula_moiety         'C9 H11 N3 S2'
_chemical_formula_sum            'C9 H11 N3 S2'
_chemical_formula_weight         225.33
_chemical_name_systematic
;
4-Ethyl-3-(2-thienylmethyl)-Δ²-1,2,4-triazoline-5-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8130(10)
_cell_length_b                   17.119(2)
_cell_length_c                   9.8460(10)
_cell_measurement_reflns_used    69
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      6
_cell_volume                     1127.7(2)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2005)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω-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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2735
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.87
_diffrn_standards_decay_%        0.09
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.165
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.2245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                1130
_reflns_number_total             2592
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2696.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220677
_cod_database_fobs_code          2220677
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-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
N N1 0.2725(3) 0.49647(12) 0.6098(2) 0.0563(6) Uani d . 1 . .
H H1 0.1684 0.4675 0.5868 0.068 Uiso calc R 1 . .
N N2 0.4538(3) 0.46832(13) 0.6760(2) 0.0598(6) Uani d . 1 . .
C C3 0.5669(4) 0.52970(16) 0.6930(3) 0.0547(7) Uani d . 1 . .
N N4 0.4644(3) 0.59498(12) 0.6394(2) 0.0504(5) Uani d . 1 . .
C C5 0.2730(3) 0.57271(16) 0.5846(2) 0.0501(6) Uani d . 1 . .
S S1 0.08621(10) 0.62899(4) 0.50362(7) 0.0654(3) Uani d . 1 . .
C C6 0.7818(4) 0.52769(17) 0.7589(3) 0.0703(8) Uani d . 1 . .
H H6A 0.8601 0.5469 0.6933 0.084 Uiso calc R 1 . .
H H6B 0.8205 0.4739 0.7799 0.084 Uiso calc R 1 . .
S S2 0.7156(9) 0.5621(3) 1.0253(6) 0.0683(11) Uani d P 0.538(6) A 1
C C8 0.982(3) 0.6272(12) 0.921(2) 0.123(10) Uani d P 0.538(6) A 1
H H8 1.0760 0.6381 0.8662 0.148 Uiso calc PR 0.538(6) A 1
C C8' 0.757(3) 0.5727(13) 1.003(2) 0.079(9) Uani d P 0.462(6) A 2
H H8' 0.6549 0.5383 1.0138 0.094 Uiso calc PR 0.462(6) A 2
S S2' 1.0016(7) 0.6482(5) 0.9087(7) 0.0949(14) Uani d P 0.462(6) A 2
C C7 0.8316(5) 0.57473(19) 0.8885(3) 0.0588(8) Uani d . 1 . .
C C9 0.9766(6) 0.6655(2) 1.0589(5) 0.1017(13) Uani d . 1 . .
H H9 1.0536 0.7077 1.0974 0.122 Uiso calc R 1 B 1
C C10 0.8435(6) 0.6283(2) 1.1134(3) 0.0885(10) Uani d . 1 . .
H H10 0.8241 0.6403 1.2020 0.106 Uiso calc R 1 C 1
C C11 0.5372(4) 0.67518(16) 0.6362(3) 0.0670(8) Uani d . 1 . .
H H11A 0.4782 0.6990 0.5485 0.080 Uiso calc R 1 . .
H H11B 0.6810 0.6744 0.6425 0.080 Uiso calc R 1 . .
C C12 0.4875(5) 0.72417(17) 0.7527(3) 0.0815(9) Uani d . 1 . .
H H12A 0.5369 0.7763 0.7462 0.098 Uiso calc R 1 . .
H H12B 0.5488 0.7017 0.8397 0.098 Uiso calc R 1 . .
H H12C 0.3452 0.7257 0.7463 0.098 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
C5 N1 N2 . . 113.6(2) ?
C5 N1 H1 . . 123.2 ?
N2 N1 H1 . . 123.2 ?
C3 N2 N1 . . 103.7(2) ?
N2 C3 N4 . . 111.4(2) ?
N2 C3 C6 . . 123.4(2) ?
N4 C3 C6 . . 125.2(3) ?
C5 N4 C3 . . 107.7(2) ?
C5 N4 C11 . . 123.7(2) ?
C3 N4 C11 . . 128.6(2) ?
N1 C5 N4 . . 103.6(2) ?
N1 C5 S1 . . 128.8(2) ?
N4 C5 S1 . . 127.6(2) ?
C3 C6 C7 . . 114.1(2) ?
C3 C6 H6A . . 108.7 ?
C7 C6 H6A . . 108.7 ?
C3 C6 H6B . . 108.7 ?
C7 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
C10 S2 C7 . . 93.0(4) ?
C7 C8 C9 . . 110.7(14) ?
C7 C8 H8 . . 124.7 ?
C9 C8 H8 . . 124.7 ?
C7 C8' C10 . . 116.3(13) ?
C7 C8' H8' . . 121.9 ?
C10 C8' H8' . . 121.9 ?
C9 S2' C7 . . 93.4(4) ?
C8' C7 C8 . . 102.3(15) ?
C8' C7 C6 . . 130.7(10) ?
C8 C7 C6 . . 126.8(11) ?
C8' C7 S2' . . 106.5(10) ?
C6 C7 S2' . . 122.7(4) ?
C8 C7 S2 . . 110.0(11) ?
C6 C7 S2 . . 123.0(3) ?
S2' C7 S2 . . 114.3(4) ?
C10 C9 C8 . . 107.1(7) ?
C10 C9 S2' . . 120.6(4) ?
C10 C9 H9 . . 126.5 ?
C8 C9 H9 . . 126.5 ?
S2' C9 H9 . . 112.5 ?
C9 C10 C8' . . 103.1(8) ?
C9 C10 S2 . . 118.6(4) ?
C9 C10 H10 . . 120.7 ?
C8' C10 H10 . . 136.2 ?
S2 C10 H10 . . 120.7 ?
N4 C11 C12 . . 112.3(2) ?
N4 C11 H11A . . 109.1 ?
C12 C11 H11A . . 109.1 ?
N4 C11 H11B . . 109.1 ?
C12 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.9 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 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
N1 C5 . 1.329(3) no
N1 N2 . 1.370(3) no
N1 H1 . 0.8600 ?
N2 C3 . 1.295(3) no
C3 N4 . 1.370(3) no
C3 C6 . 1.485(3) ?
N4 C5 . 1.368(3) no
N4 C11 . 1.462(3) ?
C5 S1 . 1.673(2) no
C6 C7 . 1.493(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
S2 C10 . 1.584(7) ?
S2 C7 . 1.699(6) ?
C8 C7 . 1.355(17) ?
C8 C9 . 1.51(2) ?
C8 H8 . 0.9300 ?
C8' C7 . 1.32(2) ?
C8' C10 . 1.48(2) ?
C8' H8' . 0.9300 ?
S2' C9 . 1.549(10) ?
S2' C7 . 1.695(6) ?
C9 C10 . 1.304(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.510(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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 H1 S1 3_566 0.86 2.44 3.287(3) 169 yes
C6 H6a S1 1_655 0.97 2.99 3.949(4) 172 yes
C9 H9 S1 4_676 0.93 2.97 3.659(4) 132 yes
C8' H8' S2 3_667 0.93 3.02 3.928(7) 166 yes
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 C3 . . . . 0.8(3) ?
N1 N2 C3 N4 . . . . -0.4(3) ?
N1 N2 C3 C6 . . . . -178.8(2) ?
N2 C3 N4 C5 . . . . -0.1(3) ?
C6 C3 N4 C5 . . . . 178.2(2) ?
N2 C3 N4 C11 . . . . -179.4(2) ?
C6 C3 N4 C11 . . . . -1.0(4) ?
N2 N1 C5 N4 . . . . -0.9(3) ?
N2 N1 C5 S1 . . . . 178.5(2) ?
C3 N4 C5 N1 . . . . 0.6(3) ?
C11 N4 C5 N1 . . . . 179.9(2) ?
C3 N4 C5 S1 . . . . -178.8(2) ?
C11 N4 C5 S1 . . . . 0.5(3) ?
N2 C3 C6 C7 . . . . -117.9(3) ?
N4 C3 C6 C7 . . . . 63.9(4) ?
C10 C8' C7 C8 . . . . 5(2) ?
C10 C8' C7 C6 . . . . 179.6(7) ?
C10 C8' C7 S2' . . . . -3.2(19) ?
C10 C8' C7 S2 . . . . 178(11) ?
C9 C8 C7 C8' . . . . -7.5(18) ?
C9 C8 C7 C6 . . . . 177.2(6) ?
C9 C8 C7 S2' . . . . 113(9) ?
C9 C8 C7 S2 . . . . -8.4(15) ?
C3 C6 C7 C8' . . . . 54.7(14) ?
C3 C6 C7 C8 . . . . -131.4(11) ?
C3 C6 C7 S2' . . . . -122.1(4) ?
C3 C6 C7 S2 . . . . 54.9(4) ?
C9 S2' C7 C8' . . . . 3.9(11) ?
C9 S2' C7 C8 . . . . -58(9) ?
C9 S2' C7 C6 . . . . -178.6(3) ?
C9 S2' C7 S2 . . . . 4.1(5) ?
C10 S2 C7 C8' . . . . -2(9) ?
C10 S2 C7 C8 . . . . 5.2(10) ?
C10 S2 C7 C6 . . . . 179.8(2) ?
C10 S2 C7 S2' . . . . -2.9(4) ?
C7 C8 C9 C10 . . . . 8.5(15) ?
C7 C8 C9 S2' . . . . -145(4) ?
C7 S2' C9 C10 . . . . -4.2(5) ?
C7 S2' C9 C8 . . . . 25(3) ?
C8 C9 C10 C8' . . . . -5.0(13) ?
S2' C9 C10 C8' . . . . 2.8(11) ?
C8 C9 C10 S2 . . . . -4.9(9) ?
S2' C9 C10 S2 . . . . 2.9(6) ?
C7 C8' C10 C9 . . . . 0.6(19) ?
C7 C8' C10 S2 . . . . -179(6) ?
C7 S2 C10 C9 . . . . 0.2(4) ?
C7 S2 C10 C8' . . . . 1(4) ?
C5 N4 C11 C12 . . . . 83.3(3) ?
C3 N4 C11 C12 . . . . -97.5(3) ?
