#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/72/2207289.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_2207289
loop_
_publ_author_name
'Yong-Tao Wang'
'Gui-Mei Tang'
'Da-Wei Qin'
_publ_section_title
;
 2,5-Di-4-pyridyl-1,3,4-oxadiazole--succinic acid (2/1)
;
_journal_coeditor_code           LH6512
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3623
_journal_page_last               o3624
_journal_paper_doi               10.1107/S1600536805031764
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '2C12 H8 N4 O, C4 H6 O4'
_chemical_formula_moiety         '2C12 H8 N4 O, C4 H6 O4'
_chemical_formula_sum            'C28 H22 N8 O6'
_chemical_formula_weight         566.54
_chemical_name_systematic
;
2,5-Di-4-pyridyl-1,3,4-oxadiazle--succinic acid (2/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.803(2)
_cell_angle_beta                 103.666(2)
_cell_angle_gamma                96.213(2)
_cell_formula_units_Z            1
_cell_length_a                   6.4389(9)
_cell_length_b                   9.5462(13)
_cell_length_c                   11.0415(15)
_cell_measurement_reflns_used    400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0
_cell_measurement_theta_min      7.5
_cell_volume                     651.39(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART-CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0101
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3585
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        no
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  8
_diffrn_standards_number         100
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0374
_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)+(0.0682P)²+0.0637P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                2227
_reflns_number_total             2499
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6512.cif
_cod_data_source_block           I
_cod_original_cell_volume        651.39(15)
_cod_database_code               2207289
_cod_database_fobs_code          2207289
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 0.03374(13) 0.12665(8) 0.29475(8) 0.0409(2) Uani d 1 O
O2 -0.10945(15) 0.85026(10) 0.05356(10) 0.0549(3) Uani d 1 O
H2B -0.074(3) 0.757(2) 0.0767(17) 0.086(6) Uiso d 1 H
O3 -0.44432(16) 0.74900(10) 0.03098(11) 0.0621(3) Uani d 1 O
N1 0.00205(18) 0.60445(11) 0.13035(10) 0.0437(3) Uani d 1 N
N2 0.37319(18) 0.18640(13) 0.29387(12) 0.0546(3) Uani d 1 N
N3 0.35241(19) 0.05282(13) 0.33667(12) 0.0536(3) Uani d 1 N
N4 -0.1419(2) -0.34963(13) 0.44529(12) 0.0589(3) Uani d 1 N
C1 0.2080(2) 0.58256(14) 0.16324(13) 0.0487(3) Uani d 1 C
H1A 0.310(2) 0.6544(17) 0.1509(13) 0.054(4) Uiso d 1 H
C2 0.2728(2) 0.46170(15) 0.21021(13) 0.0485(3) Uani d 1 C
H2A 0.423(3) 0.4500(17) 0.2325(15) 0.061(4) Uiso d 1 H
C3 0.1175(2) 0.35576(13) 0.22433(11) 0.0402(3) Uani d 1 C
C4 -0.0966(2) 0.37732(14) 0.19156(12) 0.0439(3) Uani d 1 C
H4A -0.209(2) 0.3105(17) 0.1992(13) 0.055(4) Uiso d 1 H
C5 -0.1459(2) 0.50273(14) 0.14452(12) 0.0452(3) Uani d 1 C
H5A -0.291(3) 0.5195(18) 0.1192(14) 0.060(4) Uiso d 1 H
C6 0.1832(2) 0.22489(13) 0.27106(11) 0.0413(3) Uani d 1 C
C7 0.1524(2) 0.02294(13) 0.33608(11) 0.0411(3) Uani d 1 C
C8 0.0470(2) -0.10319(12) 0.37423(11) 0.0405(3) Uani d 1 C
C9 0.1722(2) -0.19856(14) 0.43534(13) 0.0483(3) Uani d 1 C
H9A 0.317(3) -0.1790(16) 0.4562(14) 0.053(4) Uiso d 1 H
C10 0.0712(3) -0.31857(15) 0.46747(14) 0.0568(4) Uani d 1 C
H10A 0.157(3) -0.387(2) 0.5099(16) 0.073(5) Uiso d 1 H
C11 -0.2584(3) -0.25558(16) 0.38971(14) 0.0555(4) Uani d 1 C
H11A -0.416(3) -0.2804(18) 0.3759(15) 0.065(5) Uiso d 1 H
C12 -0.1738(2) -0.13186(14) 0.35270(12) 0.0468(3) Uani d 1 C
H12A -0.271(2) -0.0698(17) 0.3140(14) 0.056(4) Uiso d 1 H
C13 -0.3189(2) 0.85253(13) 0.03145(11) 0.0418(3) Uani d 1 C
C14 -0.3828(2) 0.99629(15) 0.00914(17) 0.0536(4) Uani d 1 C
H14A -0.305(4) 1.061(3) 0.082(2) 0.110(7) Uiso d 1 H
H14B -0.328(4) 1.032(3) -0.059(2) 0.105(7) Uiso d 1 H
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C6 O1 C7 . 102.56(9) ?
C13 O2 H2B . 109.9(11) ?
C5 N1 C1 . 117.55(11) ?
C6 N2 N3 . 106.09(11) n
C7 N3 N2 . 106.28(10) n
C11 N4 C10 . 116.29(13) ?
N1 C1 C2 . 123.31(12) ?
N1 C1 H1A . 116.4(10) ?
C2 C1 H1A . 120.3(10) ?
C1 C2 C3 . 118.85(13) ?
C1 C2 H2A . 120.7(10) ?
C3 C2 H2A . 120.5(9) ?
C4 C3 C2 . 118.53(12) ?
C4 C3 C6 . 121.92(12) ?
C2 C3 C6 . 119.54(12) ?
C3 C4 C5 . 118.30(12) ?
C3 C4 H4A . 123.0(10) ?
C5 C4 H4A . 118.7(10) ?
N1 C5 C4 . 123.46(12) ?
N1 C5 H5A . 116.3(10) ?
C4 C5 H5A . 120.2(10) ?
N2 C6 O1 . 112.58(11) ?
N2 C6 C3 . 128.00(12) ?
O1 C6 C3 . 119.42(11) ?
N3 C7 O1 . 112.48(11) ?
N3 C7 C8 . 128.24(11) ?
O1 C7 C8 . 119.28(11) ?
C12 C8 C9 . 118.14(13) ?
C12 C8 C7 . 122.42(12) ?
C9 C8 C7 . 119.44(12) ?
C10 C9 C8 . 118.90(14) ?
C10 C9 H9A . 121.0(10) ?
C8 C9 H9A . 120.0(10) ?
N4 C10 C9 . 123.89(13) ?
N4 C10 H10A . 116.4(10) ?
C9 C10 H10A . 119.7(10) ?
N4 C11 C12 . 124.69(14) ?
N4 C11 H11A . 114.6(10) ?
C12 C11 H11A . 120.7(10) ?
C8 C12 C11 . 118.07(13) ?
C8 C12 H12A . 123.2(9) ?
C11 C12 H12A . 118.8(9) ?
O3 C13 O2 . 122.76(12) ?
O3 C13 C14 . 124.15(12) ?
O2 C13 C14 . 113.08(11) ?
C14 C14 C13 2_475 114.22(14) ?
C14 C14 H14A 2_475 108.8(13) ?
C13 C14 H14A . 106.9(14) ?
C14 C14 H14B 2_475 112.1(14) ?
C13 C14 H14B . 110.3(14) ?
H14A C14 H14B . 103.9(17) ?
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
O1 C6 . 1.3560(15) n
O1 C7 . 1.3590(14) n
O2 C13 . 1.3153(15) n
O2 H2B . 0.99(2) ?
O3 C13 . 1.2057(15) n
N1 C5 . 1.3306(17) ?
N1 C1 . 1.3339(18) ?
N2 C6 . 1.2892(17) ?
N2 N3 . 1.4004(16) n
N3 C7 . 1.2868(17) n
N4 C11 . 1.329(2) n
N4 C10 . 1.331(2) n
C1 C2 . 1.3697(19) ?
C1 H1A . 0.937(16) ?
C2 C3 . 1.3886(18) ?
C2 H2A . 0.960(16) ?
C3 C4 . 1.3827(19) ?
C3 C6 . 1.4578(17) ?
C4 C5 . 1.3828(18) ?
C4 H4A . 0.937(15) ?
C5 H5A . 0.947(16) ?
C7 C8 . 1.4599(18) ?
C8 C12 . 1.3776(19) ?
C8 C9 . 1.3925(18) ?
C9 C10 . 1.370(2) ?
C9 H9A . 0.899(15) ?
C10 H10A . 0.980(19) ?
C11 C12 . 1.380(2) ?
C11 H11A . 0.991(17) ?
C12 H12A . 0.958(17) ?
C13 C14 . 1.4981(18) ?
C14 C14 2_475 1.485(3) ?
C14 H14A . 0.97(2) ?
C14 H14B . 0.97(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
O2 H2B N1 . 0.982(19) 1.695(19) 2.6741(15) 174.3(16)
C1 H1A O3 1_655 0.938(15) 2.440(14) 3.2912(18) 150.9(12)
C10 H10A N4 2_546 0.979(19) 2.599(19) 3.433(2) 143.1(15)
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_4
_geom_torsion
_geom_torsion_publ_flag
C6 N2 N3 C7 . -0.13(15) n
C5 N1 C1 C2 . 0.0(2) ?
N1 C1 C2 C3 . 0.2(2) ?
C1 C2 C3 C4 . -0.7(2) ?
C1 C2 C3 C6 . 178.38(12) ?
C2 C3 C4 C5 . 0.9(2) ?
C6 C3 C4 C5 . -178.12(11) ?
C1 N1 C5 C4 . 0.2(2) ?
C3 C4 C5 N1 . -0.7(2) ?
N3 N2 C6 O1 . -0.27(15) ?
N3 N2 C6 C3 . -179.90(13) ?
C7 O1 C6 N2 . 0.54(14) ?
C7 O1 C6 C3 . -179.80(11) ?
C4 C3 C6 N2 . 173.14(13) ?
C2 C3 C6 N2 . -5.9(2) y
C4 C3 C6 O1 . -6.47(19) ?
C2 C3 C6 O1 . 174.50(11) ?
N2 N3 C7 O1 . 0.48(15) ?
N2 N3 C7 C8 . -178.91(12) ?
C6 O1 C7 N3 . -0.62(14) ?
C6 O1 C7 C8 . 178.83(10) ?
N3 C7 C8 C12 . -170.66(13) ?
O1 C7 C8 C12 . 9.98(18) ?
N3 C7 C8 C9 . 9.7(2) y
O1 C7 C8 C9 . -169.66(11) ?
C12 C8 C9 C10 . 2.2(2) ?
C7 C8 C9 C10 . -178.15(12) ?
C11 N4 C10 C9 . -0.7(2) ?
C8 C9 C10 N4 . -0.9(2) ?
C10 N4 C11 C12 . 1.1(2) ?
C9 C8 C12 C11 . -1.84(19) ?
C7 C8 C12 C11 . 178.51(12) ?
N4 C11 C12 C8 . 0.2(2) ?
O3 C13 C14 C14 2_475 2.3(3) ?
O2 C13 C14 C14 2_475 -176.81(17) ?
