#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/78/2207818.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_2207818
loop_
_publ_author_name
'Wawrzycka-Gorczyca, Irena'
'Siwek, Agata'
'Dobosz, Maria'
_publ_section_title
;
 4-Allyl-3-(pyrazin-2-yl)-Δ²-1H-1,2,4-triazole-5(4H)-thione
;
_journal_coeditor_code           KP6075
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o128
_journal_page_last               o129
_journal_paper_doi               10.1107/S1600536805040584
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H9 N5 S'
_chemical_formula_moiety         'C9 H9 N5 S'
_chemical_formula_sum            'C9 H9 N5 S'
_chemical_formula_weight         219.27
_chemical_name_systematic
;
4-Allyl-3-(pyrazin-2-yl)-Δ²-1H-1,2,4-triazole-5(4H)-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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.736(2)
_cell_length_b                   14.750(2)
_cell_length_c                   7.913(2)
_cell_measurement_reflns_used    97
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      6
_cell_volume                     1049.3(4)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma, 1991)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2367
_diffrn_reflns_theta_full        80.26
_diffrn_reflns_theta_max         80.26
_diffrn_reflns_theta_min         4.92
_diffrn_standards_decay_%        1.41
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_T_max  0.2363
_exptl_absorpt_correction_T_min  0.1287
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Dwiggins (1975) with modifications.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.0130(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1213
_reflns_number_total             2242
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp6075.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207818
_cod_database_fobs_code          2207818
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_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_occupancy
_atom_site_type_symbol
S1 0.26677(8) 0.52957(4) 0.56937(11) 0.0685(3) Uani d 1 S
N1 0.0749(2) 0.40241(14) 0.3669(3) 0.0613(5) Uani d 1 N
N2 0.0529(2) 0.31086(13) 0.3469(3) 0.0606(5) Uani d 1 N
N4 0.26323(19) 0.34319(11) 0.5786(3) 0.0509(4) Uani d 1 N
N5 0.3049(2) 0.14705(13) 0.6434(3) 0.0600(5) Uani d 1 N
N6 0.1086(2) 0.03043(14) 0.3894(3) 0.0620(5) Uani d 1 N
C3 0.1688(2) 0.27623(15) 0.4764(3) 0.0513(5) Uani d 1 C
C5 0.2012(3) 0.42515(15) 0.5044(4) 0.0549(5) Uani d 1 C
C6 0.1897(2) 0.17799(14) 0.5002(3) 0.0505(5) Uani d 1 C
C7 0.0906(3) 0.11939(16) 0.3734(4) 0.0571(6) Uani d 1 C
C8 0.2249(3) -0.00026(18) 0.5318(4) 0.0673(7) Uani d 1 C
C9 0.3211(3) 0.05757(17) 0.6575(4) 0.0661(7) Uani d 1 C
C10 0.4093(3) 0.33613(16) 0.7315(4) 0.0549(5) Uani d 1 C
C11 0.5327(3) 0.32576(18) 0.6678(4) 0.0606(6) Uani d 1 C
C12 0.6335(4) 0.2623(2) 0.7234(5) 0.0797(8) Uani d 1 C
H1N 0.004(3) 0.4432(18) 0.289(4) 0.068(8) Uiso d 1 H
H7 0.002(3) 0.1444(19) 0.271(4) 0.067(8) Uiso d 1 H
H8 0.241(3) -0.064(2) 0.538(4) 0.071(8) Uiso d 1 H
H9 0.410(3) 0.039(2) 0.746(4) 0.078(9) Uiso d 1 H
H101 0.426(3) 0.395(2) 0.810(4) 0.079(9) Uiso d 1 H
H102 0.404(3) 0.2861(18) 0.813(4) 0.058(7) Uiso d 1 H
H11 0.537(3) 0.365(2) 0.582(5) 0.076(9) Uiso d 1 H
H121 0.710(4) 0.259(3) 0.687(6) 0.121(14) Uiso d 1 H
H122 0.628(4) 0.221(3) 0.822(5) 0.112(13) Uiso d 1 H
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 0.0724(4) 0.0431(3) 0.0884(5) -0.0047(3) 0.0290(3) -0.0037(3)
N1 0.0541(10) 0.0438(10) 0.0756(14) 0.0033(8) 0.0133(10) 0.0064(10)
N2 0.0537(10) 0.0452(10) 0.0721(14) 0.0007(7) 0.0120(9) 0.0036(9)
N4 0.0510(9) 0.0419(9) 0.0568(11) -0.0009(7) 0.0171(8) -0.0004(8)
N5 0.0592(10) 0.0469(10) 0.0635(13) 0.0005(8) 0.0120(10) 0.0048(9)
N6 0.0619(10) 0.0478(10) 0.0690(13) -0.0042(8) 0.0171(9) -0.0046(10)
C3 0.0522(11) 0.0434(10) 0.0550(12) -0.0008(8) 0.0170(10) 0.0004(9)
C5 0.0541(11) 0.0447(11) 0.0667(15) 0.0014(8) 0.0239(11) 0.0044(10)
C6 0.0497(11) 0.0424(10) 0.0566(13) -0.0013(8) 0.0172(10) 0.0011(9)
C7 0.0542(12) 0.0488(12) 0.0613(14) -0.0020(9) 0.0143(11) -0.0027(10)
C8 0.0697(15) 0.0426(11) 0.082(2) 0.0029(11) 0.0200(14) 0.0041(12)
C9 0.0643(13) 0.0500(12) 0.0688(16) 0.0023(11) 0.0088(12) 0.0064(12)
C10 0.0564(12) 0.0487(12) 0.0526(13) -0.0027(9) 0.0130(11) -0.0014(10)
C11 0.0568(12) 0.0596(13) 0.0590(15) -0.0061(10) 0.0152(11) 0.0012(12)
C12 0.0687(17) 0.0796(19) 0.089(2) 0.0106(14) 0.0282(16) 0.0030(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C5 N1 N2 113.39(19) no
C5 N1 H1N 126.0(17) no
N2 N1 H1N 120.6(17) no
C3 N2 N1 104.26(18) no
C5 N4 C3 107.09(19) no
C5 N4 C10 122.56(18) no
C3 N4 C10 130.23(18) no
C9 N5 C6 116.5(2) no
C7 N6 C8 117.1(2) no
N2 C3 N4 111.2(2) no
N2 C3 C6 121.6(2) no
N4 C3 C6 127.17(19) no
N1 C5 N4 104.1(2) no
N1 C5 S1 127.30(19) no
N4 C5 S1 128.65(19) no
N5 C6 C7 121.6(2) no
N5 C6 C3 118.6(2) no
C7 C6 C3 119.8(2) no
N6 C7 C6 121.1(2) no
N6 C7 H7 119.0(16) no
C6 C7 H7 119.8(16) no
N6 C8 C9 121.6(2) no
N6 C8 H8 116.6(18) no
C9 C8 H8 121.7(18) no
N5 C9 C8 122.1(3) no
N5 C9 H9 114.1(19) no
C8 C9 H9 123.0(19) no
N4 C10 C11 112.4(2) no
N4 C10 H101 107.8(15) no
C11 C10 H101 109.1(15) no
N4 C10 H102 108.3(14) no
C11 C10 H102 113.3(15) no
H101 C10 H102 106(2) no
C12 C11 C10 124.3(3) no
C12 C11 H11 117.9(19) no
C10 C11 H11 117.8(19) no
C11 C12 H121 123(3) no
C11 C12 H122 116(2) no
H121 C12 H122 121(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 1.671(2) yes
N1 C5 1.335(3) yes
N1 N2 1.367(3) yes
N1 H1N 0.95(3) no
N2 C3 1.303(3) yes
N4 C5 1.378(3) yes
N4 C3 1.380(3) yes
N4 C10 1.475(3) yes
N5 C9 1.329(3) no
N5 C6 1.332(3) no
N6 C7 1.323(3) no
N6 C8 1.333(3) no
C3 C6 1.465(3) no
C6 C7 1.393(3) no
C7 H7 1.00(3) no
C8 C9 1.371(4) no
C8 H8 0.94(3) no
C9 H9 0.92(3) no
C10 C11 1.479(4) yes
C10 H101 1.05(3) no
C10 H102 1.00(3) no
C11 C12 1.304(4) yes
C11 H11 0.91(3) no
C12 H121 0.89(4) no
C12 H122 1.01(4) no
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 H1N N6 2_555 0.95(3) 1.91(3) 2.844(3) 168(3) yes
C9 H9 S1 2_646 0.92(3) 2.92(3) 3.780(3) 156(3) 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
_geom_torsion_publ_flag
C5 N1 N2 C3 0.3(3) no
N1 N2 C3 N4 0.4(3) no
N1 N2 C3 C6 -178.8(2) no
C5 N4 C3 N2 -0.9(3) no
C10 N4 C3 N2 -176.8(2) no
C5 N4 C3 C6 178.3(2) no
C10 N4 C3 C6 2.3(4) yes
N2 N1 C5 N4 -0.8(3) no
N2 N1 C5 S1 179.3(2) no
C3 N4 C5 N1 0.9(2) no
C10 N4 C5 N1 177.3(2) no
C3 N4 C5 S1 -179.1(2) no
C10 N4 C5 S1 -2.8(3) no
C9 N5 C6 C7 0.8(4) no
C9 N5 C6 C3 -178.7(3) no
N2 C3 C6 N5 -175.1(2) no
N4 C3 C6 N5 5.8(4) yes
N2 C3 C6 C7 5.5(4) no
N4 C3 C6 C7 -173.6(2) no
C8 N6 C7 C6 0.2(4) no
N5 C6 C7 N6 -0.9(4) no
C3 C6 C7 N6 178.5(2) no
C7 N6 C8 C9 0.6(4) no
C6 N5 C9 C8 0.0(5) no
N6 C8 C9 N5 -0.7(5) no
C5 N4 C10 C11 -91.5(3) no
C3 N4 C10 C11 83.9(3) yes
N4 C10 C11 C12 -128.6(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1075989
