#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222065.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_2222065
loop_
_publ_author_name
'Wang, Yao'
'Wan, Rong'
'Han, Feng'
'Wang, Peng'
_publ_section_title
;
 5-(3-Pyridyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           HK2699
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1447
_journal_paper_doi               10.1107/S1600536809019564
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H6 N4 S'
_chemical_formula_moiety         'C7 H6 N4 S'
_chemical_formula_sum            'C7 H6 N4 S'
_chemical_formula_weight         178.22
_chemical_melting_point          550
_chemical_name_systematic
;
5-(3-Pyridyl)-1,3,4-thiadiazol-2-amine
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.066(2)
_cell_length_b                   7.2380(14)
_cell_length_c                   11.271(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     805.9(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_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    0.0271
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1542
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0524
_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
'calc w = 1/[σ²(Fo²)+(0.098P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                1220
_reflns_number_total             1464
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2699.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222065
_cod_database_fobs_code          2222065
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
S S 0.69244(6) 0.09005(8) 0.45516(5) 0.0434(3) Uani d . 1 . .
N N1 0.9145(3) -0.2801(4) 0.8931(2) 0.0717(7) Uani d . 1 . .
N N2 0.63999(19) 0.1376(3) 0.65128(17) 0.0421(5) Uani d . 1 . .
N N3 0.57605(19) 0.2824(3) 0.56552(18) 0.0441(5) Uani d . 1 . .
N N4 0.5428(3) 0.3989(3) 0.3599(2) 0.0595(7) Uani d . 1 . .
H H4A 0.4944 0.4890 0.3645 0.071 Uiso calc R 1 . .
H H4B 0.5580 0.3880 0.2918 0.071 Uiso calc R 1 . .
C C1 0.9215(3) -0.4300(4) 0.8284(3) 0.0634(8) Uani d . 1 . .
H H1B 0.9692 -0.5315 0.8782 0.076 Uiso calc R 1 . .
C C2 0.8626(3) -0.4435(4) 0.6931(3) 0.0628(8) Uani d . 1 . .
H H2B 0.8714 -0.5509 0.6523 0.075 Uiso calc R 1 . .
C C3 0.7896(3) -0.2946(3) 0.6177(3) 0.0547(7) Uani d . 1 . .
H H3B 0.7483 -0.3004 0.5253 0.066 Uiso calc R 1 . .
C C4 0.7792(2) -0.1374(3) 0.6817(2) 0.0407(5) Uani d . 1 . .
C C5 0.8440(3) -0.1375(4) 0.8191(3) 0.0578(7) Uani d . 1 . .
H H5A 0.8380 -0.0315 0.8628 0.069 Uiso calc R 1 . .
C C6 0.7037(2) 0.0273(3) 0.6091(2) 0.0378(5) Uani d . 1 . .
C C7 0.5946(2) 0.2753(3) 0.4591(2) 0.0407(5) Uani d . 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
S 0.0559(4) 0.0461(4) 0.0383(4) 0.0125(2) 0.0303(3) 0.0041(2)
N1 0.0875(17) 0.0765(17) 0.0569(14) 0.0339(14) 0.0375(13) 0.0256(13)
N2 0.0544(11) 0.0423(11) 0.0395(10) 0.0099(9) 0.0298(9) 0.0079(8)
N3 0.0609(12) 0.0421(11) 0.0427(11) 0.0143(9) 0.0353(9) 0.0107(8)
N4 0.0877(16) 0.0626(15) 0.0468(12) 0.0360(12) 0.0467(12) 0.0221(10)
C1 0.0656(17) 0.0579(18) 0.078(2) 0.0224(13) 0.0426(16) 0.0289(14)
C2 0.0675(17) 0.0420(15) 0.088(2) 0.0143(12) 0.0426(16) 0.0072(13)
C3 0.0616(16) 0.0471(15) 0.0563(15) 0.0085(12) 0.0273(13) 0.0009(12)
C4 0.0430(12) 0.0419(13) 0.0456(13) 0.0048(10) 0.0275(10) 0.0068(10)
C5 0.0728(17) 0.0574(16) 0.0491(14) 0.0208(13) 0.0327(13) 0.0100(12)
C6 0.0428(12) 0.0396(12) 0.0367(11) 0.0026(9) 0.0229(10) 0.0034(9)
C7 0.0505(12) 0.0425(12) 0.0359(11) 0.0087(10) 0.0256(10) 0.0030(9)
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 S C6 . . 86.65(10) ?
C1 N1 C5 . . 116.8(3) ?
C6 N2 N3 . . 113.79(18) ?
C7 N3 N2 . . 111.67(17) ?
C7 N4 H4A . . 120.0 ?
C7 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
N1 C1 C2 . . 123.7(2) ?
N1 C1 H1B . . 118.2 ?
C2 C1 H1B . . 118.2 ?
C1 C2 C3 . . 118.8(3) ?
C1 C2 H2B . . 120.6 ?
C3 C2 H2B . . 120.6 ?
C4 C3 C2 . . 119.0(3) ?
C4 C3 H3B . . 120.5 ?
C2 C3 H3B . . 120.5 ?
C3 C4 C5 . . 117.5(2) ?
C3 C4 C6 . . 122.5(2) ?
C5 C4 C6 . . 120.0(2) ?
N1 C5 C4 . . 124.1(3) ?
N1 C5 H5A . . 117.9 ?
C4 C5 H5A . . 117.9 ?
N2 C6 C4 . . 124.3(2) ?
N2 C6 S . . 113.59(17) ?
C4 C6 S . . 122.13(16) ?
N3 C7 N4 . . 123.6(2) ?
N3 C7 S . . 114.30(16) ?
N4 C7 S . . 122.07(16) ?
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
S C6 . 1.743(2) ?
S C7 . 1.736(2) ?
N1 C1 . 1.329(4) ?
N1 C5 . 1.335(3) ?
N2 N3 . 1.384(2) ?
N2 C6 . 1.289(3) ?
N3 C7 . 1.306(3) ?
N4 C7 . 1.342(3) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
C1 C2 . 1.366(4) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.385(4) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.379(3) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.383(3) ?
C4 C6 . 1.474(3) ?
C5 H5A . 0.9300 ?
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
N4 H4A N3 3_666 0.86 2.13 2.959(3) 163 yes
N4 H4B N2 4_565 0.86 2.16 3.006(3) 168 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 C1 C2 . . . . 0.9(5) ?
N1 C1 C2 C3 . . . . -0.9(5) ?
C6 N2 N3 C7 . . . . 0.0(3) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C2 C3 C4 C5 . . . . 0.5(4) ?
C2 C3 C4 C6 . . . . 179.9(2) ?
C1 N1 C5 C4 . . . . -0.1(5) ?
C3 C4 C5 N1 . . . . -0.6(4) ?
C6 C4 C5 N1 . . . . 180.0(3) ?
N3 N2 C6 C4 . . . . -179.8(2) ?
N3 N2 C6 S . . . . 0.1(3) ?
C3 C4 C6 N2 . . . . 147.8(2) ?
C5 C4 C6 N2 . . . . -32.8(3) ?
C3 C4 C6 S . . . . -32.0(3) ?
C5 C4 C6 S . . . . 147.4(2) ?
C7 S C6 N2 . . . . -0.09(18) ?
C7 S C6 C4 . . . . 179.73(19) ?
N2 N3 C7 N4 . . . . 179.7(2) ?
N2 N3 C7 S . . . . -0.1(3) ?
C6 S C7 N3 . . . . 0.10(19) ?
C6 S C7 N4 . . . . -179.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 172284
