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###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2000-07-07
_journal_date_accepted     2000-11-14
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue      2
_journal_page_first     197
_journal_page_last     198
_journal_paper_category     FO
_publ_contact_author_name     'Dr Peter J. Steel'
_publ_contact_author_address
; Department of Chemistry
University of Canterbury,
Christchurch,
New Zealand
;
_publ_contact_author_email     p.steel@chem.canterbury.ac.nz
_publ_contact_author_fax     '64 3 3642110'
_publ_contact_author_phone     '64 3 3642432'
_publ_section_title
; 4,4'-Bis(2-pyridyl)-3,3'-bis(1,2,5-thiadiazole)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Richardson, Chris'
; ?
;
; Department of Chemistry
University of Canterbury
Christchurch
New Zealand
;
    'Steel, Peter J.'
; ?
;
; Department of Chemistry
University of Canterbury
Christchurch
New Zealand
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4,4'-Di(2-pyridyl)-3,3'-bi-1,2,5-thiadiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 N6 S2'
_chemical_formula_sum     'C14 H8 N6 S2'
_chemical_formula_weight     324.38
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.330(5)
_cell_length_b     9.007(7)
_cell_length_c     12.250(10)
_cell_angle_alpha     84.427(9)
_cell_angle_beta     85.113(9)
_cell_angle_gamma     79.425(9)
_cell_volume     681.6(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2500
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     26.3
_cell_measurement_temperature     163(2)
_exptl_crystal_description     fragment
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .46
_exptl_crystal_size_mid      .34
_exptl_crystal_size_min      .10
_exptl_crystal_density_diffrn     1.580
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     332
_exptl_absorpt_coefficient_mu      .395
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1997)'
_exptl_absorpt_correction_T_min      .827
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     163(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'CCD area detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.192
_diffrn_reflns_number     8929
_diffrn_reflns_av_R_equivalents      .0389
_diffrn_reflns_av_sigmaI/netI      .0496
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     26.45
_diffrn_reflns_theta_full     26.45
_diffrn_measured_fraction_theta_max      .986
_diffrn_measured_fraction_theta_full      .986
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     2772
_reflns_number_gt     2016
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0566
_refine_ls_R_factor_gt      .0378
_refine_ls_wR_factor_ref      .0988
_refine_ls_goodness_of_fit_ref      .997
_refine_ls_restrained_S_all      .997
_refine_ls_number_reflns     2772
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .307
_refine_diff_density_min      -.277
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S'  .1246  .1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART  (Bruker, 1997)'
_computing_cell_refinement     'SAINT  (Bruker, 1997)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXL97'
_computing_publication_material     'SHELXL97'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    S1 1.02092(10) 1.47534(6)  .65833(4)  .02750(17) Uani d . 1 . . S
    N2 1.1480(3) 1.4958(2)  .76517(14)  .0262(4) Uani d . 1 . . N
    C3 1.2951(4) 1.5803(2)  .73078(16)  .0221(5) Uani d . 1 . . C
    C4 1.2979(3) 1.6236(2)  .61533(16)  .0215(5) Uani d . 1 . . C
    N5 1.1510(3) 1.57081(19)  .56533(14)  .0250(4) Uani d . 1 . . N
    S1' 1.71557(10) 1.59798(7)  .93400(5)  .03302(19) Uani d . 1 . . S
    N2' 1.6058(3) 1.5220(2)  .84172(14)  .0277(5) Uani d . 1 . . N
    C3' 1.4317(4) 1.6197(2)  .81288(16)  .0227(5) Uani d . 1 . . C
    C4' 1.3944(4) 1.7562(2)  .86977(17)  .0240(5) Uani d . 1 . . C
    N5' 1.5441(3) 1.7557(2)  .94043(14)  .0296(5) Uani d . 1 . . N
    N1" 1.5872(3) 1.7645(2)  .60468(14)  .0268(4) Uani d . 1 . . N
    C2" 1.4435(4) 1.7140(2)  .54934(17)  .0233(5) Uani d . 1 . . C
    C3" 1.4289(4) 1.7409(2)  .43606(17)  .0290(5) Uani d . 1 . . C
    H3" 1.3232 1.7044  .4006  .035 Uiso calc R 1 . . H
    C4" 1.5715(4) 1.8219(3)  .37657(19)  .0350(6) Uani d . 1 . . C
    H4" 1.5665 1.8418  .2992  .042 Uiso calc R 1 . . H
    C5" 1.7224(4) 1.8737(3)  .43202(19)  .0328(6) Uani d . 1 . . C
    H5" 1.8226 1.9297  .3932  .039 Uiso calc R 1 . . H
    C6" 1.7244(4) 1.8425(2)  .54456(19)  .0313(6) Uani d . 1 . . C
    H6" 1.8288 1.8782  .5816  .038 Uiso calc R 1 . . H
    N1"' 1.0419(3) 1.8628(2)  .80906(15)  .0279(4) Uani d . 1 . . N
    C2"' 1.2170(4) 1.8873(2)  .85649(16)  .0248(5) Uani d . 1 . . C
    C3"' 1.2279(4) 2.0274(2)  .89459(17)  .0281(5) Uani d . 1 . . C
    H3"' 1.3522 2.0413  .9279  .034 Uiso calc R 1 . . H
    C4"' 1.0552(4) 2.1448(3)  .88290(17)  .0317(6) Uani d . 1 . . C
    H4"' 1.0610 2.2411  .9069  .038 Uiso calc R 1 . . H
    C5"'  .8734(4) 2.1217(3)  .83603(18)  .0318(6) Uani d . 1 . . C
    H5"'  .7518 2.2003  .8282  .038 Uiso calc R 1 . . H
    C6"'  .8753(4) 1.9786(3)  .80072(17)  .0311(6) Uani d . 1 . . C
    H6"'  .7509 1.9621  .7688  .037 Uiso calc R 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  .0316(4)  .0315(3)  .0229(3)  -.0141(3)  -.0007(2)  -.0040(2)
    N2  .0324(12)  .0269(10)  .0217(10)  -.0116(9)  .0006(8)  -.0045(8)
    C3  .0258(13)  .0195(11)  .0214(11)  -.0053(9)  .0020(9)  -.0044(8)
    C4  .0226(12)  .0206(11)  .0216(11)  -.0035(9)  -.0008(9)  -.0039(8)
    N5  .0277(11)  .0277(10)  .0210(10)  -.0082(8)  -.0013(8)  -.0035(8)
    S1'  .0294(4)  .0440(4)  .0273(3)  -.0078(3)  -.0050(3)  -.0062(3)
    N2'  .0295(12)  .0337(11)  .0216(10)  -.0103(9)  .0000(8)  -.0033(8)
    C3'  .0276(13)  .0266(12)  .0153(11)  -.0116(10)  .0033(9)  .0003(9)
    C4'  .0277(13)  .0294(12)  .0173(11)  -.0139(10)  .0022(9)  -.0011(9)
    N5'  .0310(12)  .0399(12)  .0226(10)  -.0167(9)  -.0008(8)  -.0063(8)
    N1"  .0271(11)  .0289(10)  .0257(10)  -.0088(9)  .0000(8)  -.0036(8)
    C2"  .0263(13)  .0218(11)  .0215(11)  -.0050(9)  .0027(9)  -.0022(9)
    C3"  .0297(14)  .0335(13)  .0247(12)  -.0088(11)  -.0017(10)  -.0009(10)
    C4"  .0350(15)  .0395(14)  .0254(13)  -.0013(12)  .0050(11)  .0060(10)
    C5"  .0290(14)  .0304(13)  .0366(14)  -.0070(11)  .0109(11)  .0014(10)
    C6"  .0284(14)  .0297(13)  .0379(14)  -.0106(11)  .0005(11)  -.0049(10)
    N1"'  .0302(12)  .0299(10)  .0258(10)  -.0089(9)  -.0024(8)  -.0058(8)
    C2"'  .0317(14)  .0284(12)  .0160(11)  -.0120(10)  .0038(9)  -.0028(9)
    C3"'  .0386(15)  .0303(12)  .0195(12)  -.0172(11)  -.0007(10)  -.0027(9)
    C4"'  .0486(17)  .0258(12)  .0222(12)  -.0120(12)  .0014(11)  -.0025(9)
    C5"'  .0415(16)  .0285(13)  .0230(12)  -.0027(11)  .0019(11)  .0000(9)
    C6"'  .0316(15)  .0366(14)  .0262(13)  -.0086(11)  -.0020(10)  -.0021(10)
_geom_special_details
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1 N5 . 1.6202(19) ?
    S1 N2 . 1.635(2) ?
    N2 C3 . 1.325(3) ?
    C3 C4 . 1.430(3) ?
    C3 C3' . 1.488(3) ?
    C4 N5 . 1.334(3) ?
    C4 C2" . 1.479(3) ?
    S1' N5' . 1.626(2) ?
    S1' N2' . 1.639(2) ?
    N2' C3' . 1.328(3) ?
    C3' C4' . 1.444(3) ?
    C4' N5' . 1.336(3) ?
    C4' C2"' . 1.479(3) ?
    N1" C6" . 1.343(3) ?
    N1" C2" . 1.346(3) ?
    C2" C3" . 1.393(3) ?
    C3" C4" . 1.380(3) ?
    C4" C5" . 1.388(3) ?
    C5" C6" . 1.381(3) ?
    N1"' C6"' . 1.343(3) ?
    N1"' C2"' . 1.356(3) ?
    C2"' C3"' . 1.402(3) ?
    C3"' C4"' . 1.381(3) ?
    C4"' C5"' . 1.386(3) ?
    C5"' C6"' . 1.396(3) ?
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
    N5 S1 N2 . . 98.96(11) ?
    C3 N2 S1 . . 107.35(15) ?
    N2 C3 C4 . . 113.15(19) ?
    N2 C3 C3' . . 118.53(18) ?
    C4 C3 C3' . . 128.32(18) ?
    N5 C4 C3 . . 113.15(18) ?
    N5 C4 C2" . . 119.22(19) ?
    C3 C4 C2" . . 127.62(19) ?
    C4 N5 S1 . . 107.39(15) ?
    N5' S1' N2' . . 98.92(11) ?
    C3' N2' S1' . . 107.18(16) ?
    N2' C3' C4' . . 113.6(2) ?
    N2' C3' C3 . . 119.54(19) ?
    C4' C3' C3 . . 126.8(2) ?
    N5' C4' C3' . . 112.2(2) ?
    N5' C4' C2"' . . 120.39(19) ?
    C3' C4' C2"' . . 127.4(2) ?
    C4' N5' S1' . . 108.04(15) ?
    C6" N1" C2" . . 116.51(19) ?
    N1" C2" C3" . . 123.70(19) ?
    N1" C2" C4 . . 116.31(19) ?
    C3" C2" C4 . . 120.0(2) ?
    C4" C3" C2" . . 118.5(2) ?
    C3" C4" C5" . . 118.7(2) ?
    C6" C5" C4" . . 118.9(2) ?
    N1" C6" C5" . . 123.7(2) ?
    C6"' N1"' C2"' . . 117.3(2) ?
    N1"' C2"' C3"' . . 122.2(2) ?
    N1"' C2"' C4' . . 116.37(19) ?
    C3"' C2"' C4' . . 121.4(2) ?
    C4"' C3"' C2"' . . 119.0(2) ?
    C3"' C4"' C5"' . . 119.8(2) ?
    C4"' C5"' C6"' . . 117.6(2) ?
    N1"' C6"' C5"' . . 124.2(2) ?
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
    N5 S1 N2 C3 . . . .  .78(16) ?
    S1 N2 C3 C4 . . . .  -.7(2) ?
    S1 N2 C3 C3' . . . . 178.60(16) ?
    N2 C3 C4 N5 . . . .  .3(3) ?
    C3' C3 C4 N5 . . . . -178.9(2) ?
    N2 C3 C4 C2" . . . . -178.5(2) ?
    C3' C3 C4 C2" . . . . 2.3(4) ?
    C3 C4 N5 S1 . . . .  .3(2) ?
    C2" C4 N5 S1 . . . . 179.16(16) ?
    N2 S1 N5 C4 . . . .  -.62(16) ?
    N5' S1' N2' C3' . . . .  .49(15) ?
    S1' N2' C3' C4' . . . .  -.3(2) ?
    S1' N2' C3' C3 . . . . -178.95(14) ?
    N2 C3 C3' N2' . . . . 83.5(3) ?
    C4 C3 C3' N2' . . . . -97.3(3) ?
    N2 C3 C3' C4' . . . . -95.0(3) ?
    C4 C3 C3' C4' . . . . 84.2(3) ?
    N2' C3' C4' N5' . . . .  -.1(2) ?
    C3 C3' C4' N5' . . . . 178.45(18) ?
    N2' C3' C4' C2"' . . . . 179.57(19) ?
    C3 C3' C4' C2"' . . . . -1.9(3) ?
    C3' C4' N5' S1' . . . .  .4(2) ?
    C2"' C4' N5' S1' . . . . -179.26(15) ?
    N2' S1' N5' C4' . . . .  -.54(15) ?
    C6" N1" C2" C3" . . . . -1.2(3) ?
    C6" N1" C2" C4 . . . . 177.90(19) ?
    N5 C4 C2" N1" . . . . 179.71(18) ?
    C3 C4 C2" N1" . . . . -1.6(3) ?
    N5 C4 C2" C3" . . . . -1.2(3) ?
    C3 C4 C2" C3" . . . . 177.5(2) ?
    N1" C2" C3" C4" . . . . 1.0(3) ?
    C4 C2" C3" C4" . . . . -178.1(2) ?
    C2" C3" C4" C5" . . . .  -.3(3) ?
    C3" C4" C5" C6" . . . .  .0(3) ?
    C2" N1" C6" C5" . . . .  .8(3) ?
    C4" C5" C6" N1" . . . .  -.2(4) ?
    C6"' N1"' C2"' C3"' . . . .  -.7(3) ?
    C6"' N1"' C2"' C4' . . . . 177.12(18) ?
    N5' C4' C2"' N1"' . . . . -161.73(18) ?
    C3' C4' C2"' N1"' . . . . 18.6(3) ?
    N5' C4' C2"' C3"' . . . . 16.1(3) ?
    C3' C4' C2"' C3"' . . . . -163.48(19) ?
    N1"' C2"' C3"' C4"' . . . .  -.4(3) ?
    C4' C2"' C3"' C4"' . . . . -178.16(19) ?
    C2"' C3"' C4"' C5"' . . . . 1.3(3) ?
    C3"' C4"' C5"' C6"' . . . . -1.0(3) ?
    C2"' N1"' C6"' C5"' . . . . 1.1(3) ?
    C4"' C5"' C6"' N1"' . . . .  -.2(3) ?
