#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/87/2228719.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_2228719
loop_
_publ_author_name
'Tsai, Ta-Pin'
'Hsiao, Hui-Lin'
'Chen, Jhy-Der'
_publ_section_title
;
 N,N'-Bis(pyridin-2-yl)benzene-1,4-dicarboxamide
;
_journal_coeditor_code           GK2331
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o63
_journal_paper_doi               10.1107/S1600536810051172
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H14 N4 O2'
_chemical_formula_moiety         'C18 H14 N4 O2'
_chemical_formula_sum            'C18 H14 N4 O2'
_chemical_formula_weight         318.33
_chemical_name_systematic
;
N,N'-Bis(pyridin-2-yl)benzene-1,4-dicarboxamide
;
_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                82.906(6)
_cell_angle_beta                 74.083(5)
_cell_angle_gamma                73.695(6)
_cell_formula_units_Z            1
_cell_length_a                   5.7895(4)
_cell_length_b                   7.8315(6)
_cell_length_c                   8.8460(5)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14.99
_cell_measurement_theta_min      4.80
_cell_volume                     369.72(5)
_computing_cell_refinement       'XSCANS (Siemens, 1995)'
_computing_data_collection       'XSCANS (Siemens, 1995)'
_computing_data_reduction        'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1962
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1995)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             166
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.56
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.193(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0399
_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)+(0.0468P)²+0.1049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                1521
_reflns_number_total             1787
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2331.cif
_cod_data_source_block           I
_cod_original_cell_volume        369.72(4)
_cod_database_code               2228719
_cod_database_fobs_code          2228719
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O 1.1101(2) 0.21659(16) 0.30550(13) 0.0497(3) Uani d . 1 . .
N N1 0.7461(2) 0.13586(16) 0.41052(13) 0.0369(3) Uani d . 1 . .
H H1A 0.6695 0.0611 0.3982 0.044 Uiso calc R 1 . .
N N2 0.4263(2) 0.20173(15) 0.63054(13) 0.0353(3) Uani d . 1 . .
C C1 0.6435(2) 0.23152(17) 0.54787(14) 0.0316(3) Uani d . 1 . .
C C2 0.7512(3) 0.35023(19) 0.59089(16) 0.0393(3) Uani d . 1 . .
H H2B 0.9066 0.3632 0.5336 0.047 Uiso calc R 1 . .
C C3 0.6200(3) 0.4479(2) 0.72110(18) 0.0434(4) Uani d . 1 . .
H H3A 0.6853 0.5296 0.7523 0.052 Uiso calc R 1 . .
C C4 0.3907(3) 0.42384(19) 0.80528(17) 0.0422(3) Uani d . 1 . .
H H4A 0.2982 0.4900 0.8924 0.051 Uiso calc R 1 . .
C C5 0.3035(3) 0.29915(19) 0.75631(16) 0.0381(3) Uani d . 1 . .
H H5A 0.1507 0.2816 0.8138 0.046 Uiso calc R 1 . .
C C6 0.9524(2) 0.14708(17) 0.29436(15) 0.0322(3) Uani d . 1 . .
C C7 0.9716(2) 0.06764(16) 0.14401(14) 0.0290(3) Uani d . 1 . .
C C8 1.2030(2) -0.03051(17) 0.06322(14) 0.0314(3) Uani d . 1 . .
H H8A 1.3391 -0.0509 0.1057 0.038 Uiso calc R 1 . .
C C9 1.2324(2) -0.09833(17) -0.08032(15) 0.0321(3) Uani d . 1 . .
H H9A 1.3876 -0.1641 -0.1340 0.039 Uiso calc R 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
O 0.0418(6) 0.0697(7) 0.0464(6) -0.0318(5) -0.0005(5) -0.0194(5)
N1 0.0417(6) 0.0460(6) 0.0291(5) -0.0261(5) -0.0008(5) -0.0092(5)
N2 0.0366(6) 0.0411(6) 0.0302(5) -0.0166(5) -0.0041(4) -0.0045(4)
C1 0.0368(6) 0.0353(6) 0.0256(6) -0.0148(5) -0.0065(5) -0.0023(5)
C2 0.0426(7) 0.0445(8) 0.0364(7) -0.0224(6) -0.0055(6) -0.0067(6)
C3 0.0532(9) 0.0383(7) 0.0443(8) -0.0182(6) -0.0115(7) -0.0100(6)
C4 0.0491(8) 0.0360(7) 0.0382(7) -0.0074(6) -0.0055(6) -0.0110(5)
C5 0.0360(7) 0.0401(7) 0.0353(7) -0.0101(6) -0.0029(5) -0.0041(5)
C6 0.0332(6) 0.0359(6) 0.0298(6) -0.0144(5) -0.0052(5) -0.0039(5)
C7 0.0300(6) 0.0323(6) 0.0259(6) -0.0139(5) -0.0030(4) -0.0015(4)
C8 0.0267(6) 0.0384(7) 0.0308(6) -0.0119(5) -0.0068(5) -0.0011(5)
C9 0.0263(6) 0.0359(6) 0.0320(6) -0.0084(5) -0.0020(5) -0.0057(5)
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C1 . . 127.85(11) ?
C6 N1 H1A . . 116.1 ?
C1 N1 H1A . . 116.1 ?
C1 N2 C5 . . 117.11(11) ?
N2 C1 C2 . . 123.38(12) ?
N2 C1 N1 . . 112.88(11) ?
C2 C1 N1 . . 123.70(12) ?
C3 C2 C1 . . 117.84(13) ?
C3 C2 H2B . . 121.1 ?
C1 C2 H2B . . 121.1 ?
C2 C3 C4 . . 119.75(13) ?
C2 C3 H3A . . 120.1 ?
C4 C3 H3A . . 120.1 ?
C5 C4 C3 . . 118.06(13) ?
C5 C4 H4A . . 121.0 ?
C3 C4 H4A . . 121.0 ?
N2 C5 C4 . . 123.77(13) ?
N2 C5 H5A . . 118.1 ?
C4 C5 H5A . . 118.1 ?
O C6 N1 . . 124.94(12) ?
O C6 C7 . . 120.89(11) ?
N1 C6 C7 . . 114.16(11) ?
C8 C7 C9 . 2_755 119.81(11) ?
C8 C7 C6 . . 118.37(11) ?
C9 C7 C6 2_755 . 121.72(11) ?
C9 C8 C7 . . 120.42(12) ?
C9 C8 H8A . . 119.8 ?
C7 C8 H8A . . 119.8 ?
C8 C9 C7 . 2_755 119.77(11) ?
C8 C9 H9A . . 120.1 ?
C7 C9 H9A 2_755 . 120.1 ?
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
O C6 . 1.2169(16) ?
N1 C6 . 1.3614(16) ?
N1 C1 . 1.4034(16) ?
N1 H1A . 0.8600 ?
N2 C1 . 1.3375(17) ?
N2 C5 . 1.3403(17) ?
C1 C2 . 1.3932(18) ?
C2 C3 . 1.378(2) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.384(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.377(2) ?
C4 H4A . 0.9300 ?
C5 H5A . 0.9300 ?
C6 C7 . 1.5009(17) ?
C7 C8 . 1.3888(17) ?
C7 C9 2_755 1.3936(17) ?
C8 C9 . 1.3860(17) ?
C8 H8A . 0.9300 ?
C9 C7 2_755 1.3936(17) ?
C9 H9A . 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
N1 H1A N2 2_656 0.86 2.34 3.1679(15) 163
