#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215513.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_2215513
loop_
_publ_author_name
'Zhang, Yu-Xia'
'Liu, Peng'
_publ_section_title
;
 (2-Pyridyl)bis(1,3,4-thiadiazol-2-ylamino)methane
;
_journal_coeditor_code           HB2543
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4128
_journal_page_last               o4128
_journal_paper_doi               10.1107/S1600536807045473
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H9 N7 S2'
_chemical_formula_moiety         'C10 H9 N7 S2'
_chemical_formula_sum            'C10 H9 N7 S2'
_chemical_formula_weight         291.36
_chemical_name_systematic
;
(2-Pyridyl)bis(1,3,4-thiadiazol-2-ylamino)methane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.283(2)
_cell_length_b                   8.7613(18)
_cell_length_c                   13.151(3)
_cell_measurement_reflns_used    12640
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.395
_cell_volume                     1290.0(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5688
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                1908
_reflns_number_total             2953
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2543.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215513
_cod_database_fobs_code          2215513
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C C1 0.39112(15) 0.06831(18) 0.76159(12) 0.0325(4) Uani d . 1
C C2 0.55007(17) -0.0844(2) 0.82008(16) 0.0514(5) Uani d . 1
H H2 0.5793 -0.1714 0.8552 0.062 Uiso calc R 1
C C3 0.62985(18) 0.0092(2) 0.77961(16) 0.0526(5) Uani d . 1
H H3 0.7109 -0.0138 0.7871 0.063 Uiso calc R 1
C C4 0.58714(18) 0.1363(2) 0.72823(15) 0.0508(5) Uani d . 1
H H4 0.6389 0.2016 0.6996 0.061 Uiso calc R 1
C C5 0.46582(17) 0.1680(2) 0.71879(13) 0.0429(5) Uani d . 1
H H5 0.4353 0.2549 0.6843 0.052 Uiso calc R 1
C C6 0.25742(15) 0.09060(19) 0.75500(12) 0.0345(4) Uani d . 1
H H6 0.2199 -0.0105 0.7517 0.041 Uiso calc R 1
C C7 0.17955(14) 0.10493(19) 0.57373(13) 0.0345(4) Uani d . 1
C C8 0.1164(2) 0.0319(2) 0.40249(15) 0.0539(5) Uani d . 1
H H8 0.0864 0.0218 0.3337 0.065 Uiso calc R 1
C C9 0.11296(16) 0.1562(2) 0.86842(13) 0.0381(4) Uani d . 1
C C10 -0.0725(2) 0.1710(3) 0.93144(19) 0.0695(7) Uani d . 1
H H10 -0.1392 0.1909 0.9644 0.083 Uiso calc R 1
N N1 0.43237(13) -0.05732(15) 0.81182(12) 0.0411(4) Uani d . 1
N N2 0.20837(14) 0.17587(16) 0.66401(11) 0.0410(4) Uani d . 1
H H2A 0.1978 0.2728 0.6682 0.049 Uiso calc R 1
N N3 0.20509(14) -0.03795(17) 0.55573(11) 0.0433(4) Uani d . 1
N N4 0.16735(16) -0.07900(18) 0.45482(12) 0.0534(4) Uani d . 1
N N5 0.22648(13) 0.16712(16) 0.84586(11) 0.0388(4) Uani d . 1
H H5A 0.2792 0.2184 0.8846 0.047 Uiso calc R 1
N N6 0.03642(14) 0.05646(18) 0.82607(13) 0.0496(4) Uani d . 1
N N7 -0.07234(16) 0.0652(2) 0.86360(15) 0.0657(5) Uani d . 1
S S1 0.10722(5) 0.20038(6) 0.46841(4) 0.04768(17) Uani d . 1
S S2 0.05728(5) 0.27312(7) 0.95736(4) 0.06054(19) Uani d . 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
N1 C1 C5 121.96(17)
N1 C1 C6 114.72(14)
C5 C1 C6 123.32(16)
N1 C2 C3 123.64(19)
N1 C2 H2 118.2
C3 C2 H2 118.2
C4 C3 C2 118.21(19)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C5 119.58(18)
C3 C4 H4 120.2
C5 C4 H4 120.2
C1 C5 C4 118.80(18)
C1 C5 H5 120.6
C4 C5 H5 120.6
N5 C6 N2 109.47(14)
N5 C6 C1 110.65(14)
N2 C6 C1 112.76(14)
N5 C6 H6 107.9
N2 C6 H6 107.9
C1 C6 H6 107.9
N3 C7 N2 124.47(16)
N3 C7 S1 114.09(13)
N2 C7 S1 121.42(13)
N4 C8 S1 115.44(15)
N4 C8 H8 122.3
S1 C8 H8 122.3
N6 C9 N5 123.27(16)
N6 C9 S2 114.12(14)
N5 C9 S2 122.60(13)
N7 C10 S2 116.03(17)
N7 C10 H10 122.0
S2 C10 H10 122.0
C1 N1 C2 117.80(16)
C7 N2 C6 120.86(14)
C7 N2 H2A 119.6
C6 N2 H2A 119.6
C7 N3 N4 111.77(15)
C8 N4 N3 112.31(15)
C9 N5 C6 118.61(14)
C9 N5 H5A 120.7
C6 N5 H5A 120.7
C9 N6 N7 112.40(16)
C10 N7 N6 111.47(18)
C8 S1 C7 86.39(10)
C10 S2 C9 85.96(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.337(2)
C1 C5 1.382(2)
C1 C6 1.513(2)
C2 N1 1.340(2)
C2 C3 1.373(3)
C2 H2 0.9300
C3 C4 1.360(3)
C3 H3 0.9300
C4 C5 1.387(3)
C4 H4 0.9300
C5 H5 0.9300
C6 N5 1.450(2)
C6 N2 1.460(2)
C6 H6 0.9800
C7 N3 1.313(2)
C7 N2 1.344(2)
C7 S1 1.7330(18)
C8 N4 1.284(2)
C8 S1 1.722(2)
C8 H8 0.9300
C9 N6 1.304(2)
C9 N5 1.354(2)
C9 S2 1.7307(18)
C10 N7 1.287(3)
C10 S2 1.714(2)
C10 H10 0.9300
N2 H2A 0.8600
N3 N4 1.390(2)
N5 H5A 0.8600
N6 N7 1.380(2)
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
N2 H2A N1 2_556 0.86 2.13 2.866(2) 143
N5 H5A N3 2_556 0.86 2.27 2.949(2) 136
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
N1 C2 C3 C4 0.0(3)
C2 C3 C4 C5 0.4(3)
N1 C1 C5 C4 0.1(3)
C6 C1 C5 C4 -179.31(15)
C3 C4 C5 C1 -0.4(3)
N1 C1 C6 N5 85.31(18)
C5 C1 C6 N5 -95.21(18)
N1 C1 C6 N2 -151.70(15)
C5 C1 C6 N2 27.8(2)
C5 C1 N1 C2 0.2(3)
C6 C1 N1 C2 179.69(15)
C3 C2 N1 C1 -0.3(3)
N3 C7 N2 C6 -8.6(3)
S1 C7 N2 C6 173.28(12)
N5 C6 N2 C7 -151.96(15)
C1 C6 N2 C7 84.40(19)
N2 C7 N3 N4 -178.27(15)
S1 C7 N3 N4 0.01(19)
S1 C8 N4 N3 0.0(2)
C7 N3 N4 C8 0.0(2)
N6 C9 N5 C6 14.7(3)
S2 C9 N5 C6 -165.92(13)
N2 C6 N5 C9 74.84(19)
C1 C6 N5 C9 -160.28(14)
N5 C9 N6 N7 178.40(17)
S2 C9 N6 N7 -1.1(2)
S2 C10 N7 N6 0.5(3)
C9 N6 N7 C10 0.4(3)
N4 C8 S1 C7 0.04(17)
N3 C7 S1 C8 -0.03(15)
N2 C7 S1 C8 178.31(15)
N7 C10 S2 C9 -0.9(2)
N6 C9 S2 C10 1.09(16)
N5 C9 S2 C10 -178.39(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123359
2 PubChem 139073147
