#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504995.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4504995
loop_
_publ_author_name
'Bowers, Jeffrey R.'
'Hopkins, Gregory W.'
'Yap, Glenn P. A.'
'Wheeler, Kraig A.'
_publ_section_title
;
 Structural Consequences of Strong and Weak Interactions to Binary Benzoic
 Acid/Bipyridine Supramolecular Assemblies
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              727
_journal_paper_doi               10.1021/cg0497391
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         'C5 H4 N1, C7 H5 N1 O4'
_chemical_formula_sum            'C12 H9 N2 O4'
_chemical_formula_weight         245.21
_chemical_name_systematic
; 
 4-Nitrobenzoic acid 4,4'-bipyridine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.559(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8386(4)
_cell_length_b                   6.8499(4)
_cell_length_c                   20.7925(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.993
_cell_measurement_theta_min      22.839
_cell_volume                     1115.31(10)
_computing_cell_refinement       'XSCANS (Bruker, 1999)'
_computing_data_collection       'XSCANS (Bruker, 1999)'
_computing_data_reduction        'XSCANS (Bruker, 1999)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'θ/2θ\ scans'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3618
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0554
_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)+(0.0646P)²+0.1385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                1420
_reflns_number_total             2565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0497391si20040728_090350.cif
_cod_data_source_block           cmpd2.4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4504995
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2292(2) 1.2289(2) 0.35637(7) 0.0637(5) Uani 1 1 d .
HO1 H 0.277(3) 1.114(4) 0.3808(12) 0.076 Uiso 1 1 d .
O2 O 0.0975(2) 1.2788(3) 0.44688(8) 0.0810(6) Uani 1 1 d .
O3 O -0.2137(3) 2.1464(3) 0.32353(10) 0.0874(6) Uani 1 1 d .
O4 O -0.0891(3) 2.0954(3) 0.23557(9) 0.0917(7) Uani 1 1 d .
N1 N -0.1256(3) 2.0476(3) 0.28950(10) 0.0636(6) Uani 1 1 d .
N2 N 0.3477(2) 0.9204(3) 0.41624(9) 0.0550(5) Uani 1 1 d .
C1 C 0.1314(3) 1.3293(3) 0.39331(10) 0.0516(6) Uani 1 1 d .
C2 C 0.0657(2) 1.5152(3) 0.36443(9) 0.0456(5) Uani 1 1 d .
C3 C 0.0945(3) 1.5682(3) 0.30099(9) 0.0530(6) Uani 1 1 d .
H3 H 0.1558 1.4851 0.2752 0.064 Uiso 1 1 calc R
C4 C 0.0332(3) 1.7415(3) 0.27628(10) 0.0548(6) Uani 1 1 d .
H4 H 0.0529 1.7771 0.2341 0.066 Uiso 1 1 calc R
C5 C -0.0576(3) 1.8613(3) 0.31511(10) 0.0494(5) Uani 1 1 d .
C6 C -0.0878(3) 1.8147(3) 0.37769(10) 0.0559(6) Uani 1 1 d .
H6 H -0.1492 1.8988 0.4031 0.067 Uiso 1 1 calc R
C7 C -0.0254(3) 1.6404(3) 0.40225(10) 0.0544(6) Uani 1 1 d .
H7 H -0.0448 1.6067 0.4446 0.065 Uiso 1 1 calc R
C8 C 0.3037(4) 0.8813(4) 0.47564(11) 0.0707(7) Uani 1 1 d .
H8 H 0.2305 0.9675 0.4952 0.085 Uiso 1 1 calc R
C9 C 0.3599(3) 0.7208(4) 0.50990(11) 0.0692(7) Uani 1 1 d .
H9 H 0.3250 0.7012 0.5516 0.083 Uiso 1 1 calc R
C10 C 0.4680(3) 0.5882(3) 0.48264(9) 0.0453(5) Uani 1 1 d .
C11 C 0.5117(3) 0.6281(3) 0.42012(10) 0.0572(6) Uani 1 1 d .
H11 H 0.5824 0.5430 0.3988 0.069 Uiso 1 1 calc R
C12 C 0.4503(3) 0.7937(4) 0.38952(11) 0.0611(6) Uani 1 1 d .
H12 H 0.4828 0.8177 0.3478 0.073 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_3
C1 O1 HO1 109.4(13) .
O4 N1 O3 123.4(2) .
O4 N1 C5 118.1(2) .
O3 N1 C5 118.5(2) .
C12 N2 C8 116.6(2) .
O2 C1 O1 123.5(2) .
O2 C1 C2 122.02(19) .
O1 C1 C2 114.51(17) .
C7 C2 C3 119.0(2) .
C7 C2 C1 118.60(17) .
C3 C2 C1 122.36(19) .
C4 C3 C2 120.7(2) .
C4 C3 H3 119.7 .
C2 C3 H3 119.7 .
C3 C4 C5 118.65(19) .
C3 C4 H4 120.7 .
C5 C4 H4 120.7 .
C6 C5 C4 122.3(2) .
C6 C5 N1 118.0(2) .
C4 C5 N1 119.62(19) .
C5 C6 C7 118.7(2) .
C5 C6 H6 120.7 .
C7 C6 H6 120.7 .
C6 C7 C2 120.64(19) .
C6 C7 H7 119.7 .
C2 C7 H7 119.7 .
N2 C8 C9 123.7(2) .
N2 C8 H8 118.1 .
C9 C8 H8 118.1 .
C8 C9 C10 120.2(2) .
C8 C9 H9 119.9 .
C10 C9 H9 119.9 .
C9 C10 C11 115.9(2) .
C9 C10 C10 122.5(2) 3_666
C11 C10 C10 121.6(2) 3_666
C12 C11 C10 120.0(2) .
C12 C11 H11 120.0 .
C10 C11 H11 120.0 .
N2 C12 C11 123.6(2) .
N2 C12 H12 118.2 .
C11 C12 H12 118.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.305(2) .
O1 HO1 1.00(3) .
O2 C1 1.207(2) .
O3 N1 1.216(2) .
O4 N1 1.215(2) .
N1 C5 1.473(3) .
N2 C12 1.323(3) .
N2 C8 1.325(3) .
C1 C2 1.490(3) .
C2 C7 1.383(3) .
C2 C3 1.396(3) .
C3 C4 1.372(3) .
C3 H3 0.9300 .
C4 C5 1.373(3) .
C4 H4 0.9300 .
C5 C6 1.371(3) .
C6 C7 1.380(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.372(3) .
C8 H8 0.9300 .
C9 C10 1.381(3) .
C9 H9 0.9300 .
C10 C11 1.386(3) .
C10 C10 1.484(4) 3_666
C11 C12 1.377(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 HO1 N2 1.00(3) 1.61(3) 2.603(2) 176(2) .
C8 H8 O2 0.93 2.56 3.209(3) 127.3 .
C7 H7 O2 0.93 2.44 3.260(3) 146.9 3_586
C4 H4 O1 0.93 2.62 3.397(3) 141.8 2
C12 H12 O4 0.93 2.48 3.169(3) 131.2 2_535
C11 H11 O4 0.93 2.82 3.328(3) 115.4 2_535
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O2 C1 C2 C7 5.3(3) . .
O1 C1 C2 C7 -173.9(2) . .
O2 C1 C2 C3 -175.5(2) . .
O1 C1 C2 C3 5.4(3) . .
C7 C2 C3 C4 -0.2(3) . .
C1 C2 C3 C4 -179.4(2) . .
C2 C3 C4 C5 -0.3(3) . .
C3 C4 C5 C6 0.6(3) . .
C3 C4 C5 N1 -179.6(2) . .
O4 N1 C5 C6 175.1(2) . .
O3 N1 C5 C6 -4.2(3) . .
O4 N1 C5 C4 -4.8(3) . .
O3 N1 C5 C4 176.0(2) . .
C4 C5 C6 C7 -0.4(3) . .
N1 C5 C6 C7 179.8(2) . .
C5 C6 C7 C2 -0.1(3) . .
C3 C2 C7 C6 0.3(3) . .
C1 C2 C7 C6 179.6(2) . .
C12 N2 C8 C9 0.8(4) . .
N2 C8 C9 C10 -0.3(4) . .
C8 C9 C10 C11 -0.7(4) . .
C8 C9 C10 C10 -179.7(3) . 3_666
C9 C10 C11 C12 1.2(3) . .
C10 C10 C11 C12 -179.8(2) 3_666 .
C8 N2 C12 C11 -0.2(4) . .
C10 C11 C12 N2 -0.8(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145690
