#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/15/2221588.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_2221588
loop_
_publ_author_name
'Wang, Yao'
'Wan, Rong'
'Han, Feng'
'Wang, Peng'
'Wang, Bin'
_publ_section_title
;
 5-(4-Pyridyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           BH2224
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1099
_journal_paper_doi               10.1107/S1600536809014470
_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          543
_chemical_name_systematic
;
5-(4-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.794(3)
_cell_length_b                   10.686(2)
_cell_length_c                   10.477(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1587.9(6)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo,1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3203
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.9333
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0668
_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)+(0.0435P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                1516
_reflns_number_total             3023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2224.cif
_cod_data_source_block           I
_cod_original_cell_volume        1587.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221588
_cod_database_fobs_code          2221588
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 SA 0.08251(8) 0.54450(10) 0.19829(12) 0.0483(4) Uani d . 1 . .
N N1A 0.3034(3) 0.3300(4) -0.0749(4) 0.0551(11) Uani d . 1 . .
N N2A 0.0328(3) 0.3203(3) 0.1338(4) 0.0513(10) Uani d . 1 . .
N N3A -0.0258(2) 0.3605(3) 0.2081(4) 0.0509(10) Uani d . 1 . .
N N4A -0.0553(2) 0.5382(3) 0.3223(3) 0.0548(11) Uani d . 1 . .
H H4A -0.0999 0.5013 0.3454 0.066 Uiso calc R 1 . .
H H4B -0.0408 0.6143 0.3462 0.066 Uiso calc R 1 . .
C C1A 0.2262(3) 0.2621(5) -0.0932(4) 0.0604(14) Uani d . 1 . .
H H1B 0.2192 0.1944 -0.1510 0.073 Uiso calc R 1 . .
C C2A 0.3105(3) 0.4259(5) 0.0056(5) 0.0601(14) Uani d . 1 . .
H H2B 0.3635 0.4769 0.0204 0.072 Uiso calc R 1 . .
C C3A 0.2430(3) 0.4551(4) 0.0697(4) 0.0485(12) Uani d . 1 . .
H H3B 0.2515 0.5243 0.1256 0.058 Uiso calc R 1 . .
C C4A 0.1643(3) 0.3827(4) 0.0511(4) 0.0393(11) Uani d . 1 . .
C C5A 0.1561(3) 0.2820(4) -0.0357(4) 0.0549(13) Uani d . 1 . .
H H5A 0.1038 0.2296 -0.0538 0.066 Uiso calc R 1 . .
C C6A 0.0928(3) 0.4040(4) 0.1217(4) 0.0413(11) Uani d . 1 . .
C C7A -0.0070(3) 0.4754(4) 0.2470(4) 0.0396(11) Uani d . 1 . .
S SB 0.43176(9) 0.68957(10) -0.17070(12) 0.0505(4) Uani d . 1 . .
N N1B 0.2053(3) 0.9156(4) 0.0901(4) 0.0573(11) Uani d . 1 . .
N N2B 0.4342(3) 0.9258(3) -0.1864(4) 0.0518(11) Uani d . 1 . .
N N3B 0.4926(2) 0.8856(3) -0.2569(4) 0.0489(10) Uani d . 1 . .
N N4B 0.5574(2) 0.7052(3) -0.3157(3) 0.0456(10) Uani d U 1 . .
H H8A 0.5907 0.7475 -0.3556 0.055 Uiso calc R 1 . .
H H8B 0.5607 0.6249 -0.3136 0.055 Uiso calc R 1 . .
C C1B 0.1980(3) 0.8094(5) 0.0207(5) 0.0562(13) Uani d . 1 . .
H H8C 0.1499 0.7540 0.0226 0.067 Uiso calc R 1 . .
C C2B 0.2762(3) 0.9914(4) 0.0858(4) 0.0577(13) Uani d . 1 . .
H H9A 0.2837 1.0650 0.1352 0.069 Uiso calc R 1 . .
C C3B 0.3375(3) 0.9687(4) 0.0150(4) 0.0507(12) Uani d U 1 . .
H H10A 0.3841 1.0269 0.0141 0.061 Uiso calc R 1 . .
C C4B 0.3308(3) 0.8588(4) -0.0563(4) 0.0362(10) Uani d U 1 . .
C C5B 0.2573(3) 0.7782(4) -0.0528(4) 0.0506(12) Uani d U 1 . .
H H12A 0.2489 0.7035 -0.1003 0.061 Uiso calc R 1 . .
C C6B 0.3977(3) 0.8349(4) -0.1355(4) 0.0389(10) Uani d U 1 . .
C C7B 0.4998(3) 0.7650(4) -0.2563(4) 0.0380(10) Uani d U 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
C7A SA C6A . . 86.7(2) ?
C2A N1A C1A . . 115.6(4) ?
C6A N2A N3A . . 113.4(4) ?
C7A N3A N2A . . 110.9(3) ?
C7A N4A H4A . . 120.0 ?
C7A N4A H4B . . 120.0 ?
H4A N4A H4B . . 120.0 ?
N1A C1A C5A . . 126.0(5) ?
N1A C1A H1B . . 117.0 ?
C5A C1A H1B . . 117.0 ?
N1A C2A C3A . . 123.2(5) ?
N1A C2A H2B . . 118.4 ?
C3A C2A H2B . . 118.4 ?
C4A C3A C2A . . 120.4(4) ?
C4A C3A H3B . . 119.8 ?
C2A C3A H3B . . 119.8 ?
C3A C4A C5A . . 116.3(4) ?
C3A C4A C6A . . 123.2(4) ?
C5A C4A C6A . . 120.5(4) ?
C1A C5A C4A . . 118.5(5) ?
C1A C5A H5A . . 120.8 ?
C4A C5A H5A . . 120.8 ?
N2A C6A C4A . . 123.7(4) ?
N2A C6A SA . . 113.7(3) ?
C4A C6A SA . . 122.6(3) ?
N3A C7A N4A . . 122.7(4) ?
N3A C7A SA . . 115.3(3) ?
N4A C7A SA . . 121.9(3) ?
C6B SB C7B . . 86.5(2) ?
C1B N1B C2B . . 116.1(4) ?
C6B N2B N3B . . 113.0(3) ?
C7B N3B N2B . . 112.2(4) ?
C7B N4B H8A . . 120.0 ?
C7B N4B H8B . . 120.0 ?
H8A N4B H8B . . 120.0 ?
N1B C1B C5B . . 123.4(4) ?
N1B C1B H8C . . 118.3 ?
C5B C1B H8C . . 118.3 ?
N1B C2B C3B . . 124.5(5) ?
N1B C2B H9A . . 117.7 ?
C3B C2B H9A . . 117.7 ?
C2B C3B C4B . . 119.7(4) ?
C2B C3B H10A . . 120.2 ?
C4B C3B H10A . . 120.2 ?
C3B C4B C5B . . 116.6(4) ?
C3B C4B C6B . . 119.5(4) ?
C5B C4B C6B . . 123.9(4) ?
C1B C5B C4B . . 119.7(4) ?
C1B C5B H12A . . 120.2 ?
C4B C5B H12A . . 120.2 ?
N2B C6B C4B . . 121.5(4) ?
N2B C6B SB . . 114.2(3) ?
C4B C6B SB . . 124.3(3) ?
N3B C7B N4B . . 122.1(4) ?
N3B C7B SB . . 114.1(3) ?
N4B C7B SB . . 123.8(3) ?
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
SA C7A . 1.716(4) ?
SA C6A . 1.729(4) ?
N1A C2A . 1.312(5) ?
N1A C1A . 1.320(5) ?
N2A C6A . 1.292(5) ?
N2A N3A . 1.387(4) ?
N3A C7A . 1.298(5) ?
N4A C7A . 1.380(5) ?
N4A H4A . 0.8600 ?
N4A H4B . 0.8600 ?
C1A C5A . 1.356(6) ?
C1A H1B . 0.9300 ?
C2A C3A . 1.389(6) ?
C2A H2B . 0.9300 ?
C3A C4A . 1.365(5) ?
C3A H3B . 0.9300 ?
C4A C5A . 1.392(5) ?
C4A C6A . 1.470(5) ?
C5A H5A . 0.9300 ?
SB C6B . 1.705(4) ?
SB C7B . 1.726(4) ?
N1B C1B . 1.335(5) ?
N1B C2B . 1.336(5) ?
N2B C6B . 1.298(5) ?
N2B N3B . 1.356(4) ?
N3B C7B . 1.293(5) ?
N4B C7B . 1.349(4) ?
N4B H8A . 0.8600 ?
N4B H8B . 0.8600 ?
C1B C5B . 1.363(6) ?
C1B H8C . 0.9300 ?
C2B C3B . 1.347(5) ?
C2B H9A . 0.9300 ?
C3B C4B . 1.380(5) ?
C3B H10A . 0.9300 ?
C4B C5B . 1.396(5) ?
C4B C6B . 1.483(5) ?
C5B H12A . 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
C3A H3B SA . 0.9300 2.8200 3.191(5) 105 no
N4A H4A N1B 2_545 0.8600 2.0800 2.940(5) 177 yes
N4A H4B N2A 2_555 0.8600 2.2100 3.053(5) 166 yes
N4B H8A N1A 2_654 0.8600 2.1000 2.945(5) 168 yes
N4B H8B N2B 2_644 0.8600 2.1300 2.988(5) 178 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
C6A N2A N3A C7A . . . . 0.9(5) ?
C2A N1A C1A C5A . . . . -1.0(7) ?
C1A N1A C2A C3A . . . . 0.8(7) ?
N1A C2A C3A C4A . . . . 0.1(7) ?
C2A C3A C4A C5A . . . . -1.0(6) ?
C2A C3A C4A C6A . . . . 176.4(4) ?
N1A C1A C5A C4A . . . . 0.1(8) ?
C3A C4A C5A C1A . . . . 0.9(6) ?
C6A C4A C5A C1A . . . . -176.6(4) ?
N3A N2A C6A C4A . . . . 178.1(4) ?
N3A N2A C6A SA . . . . -1.2(5) ?
C3A C4A C6A N2A . . . . -160.7(4) ?
C5A C4A C6A N2A . . . . 16.7(6) ?
C3A C4A C6A SA . . . . 18.5(6) ?
C5A C4A C6A SA . . . . -164.1(3) ?
C7A SA C6A N2A . . . . 0.9(3) ?
C7A SA C6A C4A . . . . -178.4(4) ?
N2A N3A C7A N4A . . . . 179.9(4) ?
N2A N3A C7A SA . . . . -0.2(5) ?
C6A SA C7A N3A . . . . -0.4(3) ?
C6A SA C7A N4A . . . . 179.6(4) ?
C6B N2B N3B C7B . . . . -0.7(6) ?
C2B N1B C1B C5B . . . . -0.9(7) ?
C1B N1B C2B C3B . . . . 1.6(7) ?
N1B C2B C3B C4B . . . . -2.1(8) ?
C2B C3B C4B C5B . . . . 1.7(6) ?
C2B C3B C4B C6B . . . . 179.3(4) ?
N1B C1B C5B C4B . . . . 0.7(7) ?
C3B C4B C5B C1B . . . . -1.1(6) ?
C6B C4B C5B C1B . . . . -178.6(4) ?
N3B N2B C6B C4B . . . . -179.1(4) ?
N3B N2B C6B SB . . . . -0.4(5) ?
C3B C4B C6B N2B . . . . -29.4(6) ?
C5B C4B C6B N2B . . . . 147.9(4) ?
C3B C4B C6B SB . . . . 152.0(3) ?
C5B C4B C6B SB . . . . -30.7(6) ?
C7B SB C6B N2B . . . . 1.0(3) ?
C7B SB C6B C4B . . . . 179.7(4) ?
N2B N3B C7B N4B . . . . -177.2(4) ?
N2B N3B C7B SB . . . . 1.5(5) ?
C6B SB C7B N3B . . . . -1.4(3) ?
C6B SB C7B N4B . . . . 177.3(4) ?
