#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504992.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_4504992
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 H7 N O2'
_chemical_formula_sum            'C12 H11 N2 O2'
_chemical_formula_weight         215.23
_chemical_name_common            '4-Aminobenzoic acid 2,2'-bipyridine'
_chemical_name_systematic
; 
 4-Aminobenzoic acid 2,2'-bipyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.173(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8195(9)
_cell_length_b                   4.3087(4)
_cell_length_c                   16.4660(8)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.663
_cell_measurement_theta_min      21.407
_cell_volume                     1072.31(13)
_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 0.897
_diffrn_measured_fraction_theta_max 0.897
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3431
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0573
_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)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                1203
_reflns_number_total             2475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0497391si20040728_090350.cif
_cod_data_source_block           cmpd1.4
_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_H-M      'P 21/c'
_cod_database_code               4504992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.30217(10) 0.2739(5) 0.55914(12) 0.0656(6) Uani 1 1 d .
O2 O 0.19905(12) 0.4450(7) 0.44415(12) 0.0911(8) Uani 1 1 d .
N1 N 0.07218(13) 0.8776(6) 0.77123(16) 0.0595(7) Uani 1 1 d .
N2 N 0.40000(12) 0.1829(5) 0.44265(13) 0.0480(6) Uani 1 1 d .
C1 C 0.22770(15) 0.4145(7) 0.52302(18) 0.0579(8) Uani 1 1 d .
C2 C 0.18796(13) 0.5281(6) 0.58871(15) 0.0463(6) Uani 1 1 d .
C3 C 0.22419(14) 0.4886(7) 0.67861(15) 0.0527(7) Uani 1 1 d .
H3 H 0.2767 0.3773 0.6981 0.063 Uiso 1 1 calc R
C4 C 0.18672(14) 0.6043(7) 0.73897(16) 0.0546(7) Uani 1 1 d .
H4 H 0.2131 0.5707 0.7967 0.066 Uiso 1 1 calc R
C5 C 0.11061(14) 0.7670(6) 0.71080(16) 0.0477(6) Uani 1 1 d .
C6 C 0.07292(16) 0.8002(7) 0.62044(18) 0.0645(8) Uani 1 1 d .
H6 H 0.0195 0.9059 0.6007 0.077 Uiso 1 1 calc R
C7 C 0.11084(16) 0.6855(7) 0.56112(17) 0.0638(8) Uani 1 1 d .
H7 H 0.0839 0.7158 0.5033 0.077 Uiso 1 1 calc R
C8 C 0.36729(15) 0.3665(7) 0.37298(16) 0.0550(7) Uani 1 1 d .
H8 H 0.3077 0.4179 0.3596 0.066 Uiso 1 1 calc R
C9 C 0.41287(16) 0.4846(7) 0.32013(16) 0.0553(7) Uani 1 1 d .
H9 H 0.3859 0.6056 0.2728 0.066 Uiso 1 1 calc R
C10 C 0.49814(17) 0.4121(7) 0.34211(17) 0.0547(7) Uani 1 1 d .
H10 H 0.5341 0.4869 0.3108 0.066 Uiso 1 1 calc R
C11 C 0.53357(16) 0.2211(6) 0.41313(16) 0.0488(6) Uani 1 1 d .
H11 H 0.5933 0.1699 0.4278 0.059 Uiso 1 1 calc R
C12 C 0.48299(14) 0.1060(5) 0.46210(14) 0.0416(6) Uani 1 1 d .
HN1 H 0.1065(15) 0.898(6) 0.8261(15) 0.050 Uiso 1 1 d .
HO1 H 0.3242(16) 0.232(6) 0.5187(15) 0.050 Uiso 1 1 d .
HN2 H 0.0333(15) 1.026(6) 0.7507(15) 0.050 Uiso 1 1 d .
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 105.2(16) .
C5 N1 HN1 119.0(15) .
C5 N1 HN2 112.1(17) .
HN1 N1 HN2 117(2) .
C12 N2 C8 117.4(2) .
O2 C1 O1 121.7(3) .
O2 C1 C2 128.3(2) .
O1 C1 C2 109.9(2) .
C7 C2 C3 117.0(2) .
C7 C2 C1 117.0(2) .
C3 C2 C1 126.0(2) .
C4 C3 C2 124.9(2) .
C4 C3 H3 117.6 .
C2 C3 H3 117.6 .
C5 C4 C3 117.7(2) .
C5 C4 H4 121.1 .
C3 C4 H4 121.1 .
C4 C5 N1 117.7(2) .
C4 C5 C6 117.5(2) .
N1 C5 C6 124.7(2) .
C7 C6 C5 124.3(2) .
C7 C6 H6 117.9 .
C5 C6 H6 117.9 .
C2 C7 C6 118.7(2) .
C2 C7 H7 120.7 .
C6 C7 H7 120.7 .
N2 C8 C9 127.2(2) .
N2 C8 H8 116.4 .
C9 C8 H8 116.4 .
C10 C9 C8 114.8(3) .
C10 C9 H9 122.6 .
C8 C9 H9 122.6 .
C9 C10 C11 119.3(2) .
C9 C10 H10 120.4 .
C11 C10 H10 120.4 .
C12 C11 C10 122.5(2) .
C12 C11 H11 118.7 .
C10 C11 H11 118.7 .
N2 C12 C11 118.7(2) .
N2 C12 C12 116.4(2) 3_656
C11 C12 C12 124.8(2) 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.302(3) .
O1 HO1 0.86(3) .
O2 C1 1.250(3) .
N1 C5 1.394(3) .
N1 HN1 0.91(2) .
N1 HN2 0.88(3) .
N2 C12 1.299(3) .
N2 C8 1.364(3) .
C1 C2 1.485(4) .
C2 C7 1.352(3) .
C2 C3 1.431(3) .
C3 C4 1.391(3) .
C3 H3 0.9300 .
C4 C5 1.352(3) .
C4 H4 0.9300 .
C5 C6 1.437(4) .
C6 C7 1.380(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.381(3) .
C8 H8 0.9300 .
C9 C10 1.327(3) .
C9 H9 0.9300 .
C10 C11 1.404(3) .
C10 H10 0.9300 .
C11 C12 1.385(3) .
C11 H11 0.9300 .
C12 C12 1.512(5) 3_656
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 0.86(3) 1.98(3) 2.825(3) 167(2) .
N1 HN2 N1 0.88(3) 2.20(3) 3.066(3) 166(2) 2_556
N1 HN1 O2 0.91(2) 2.17(2) 3.057(3) 165(2) 4_576
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_4
O2 C1 C2 C7 0.0(5) .
O1 C1 C2 C7 178.7(3) .
O2 C1 C2 C3 -179.4(3) .
O1 C1 C2 C3 -0.7(4) .
C7 C2 C3 C4 -1.2(4) .
C1 C2 C3 C4 178.3(3) .
C2 C3 C4 C5 -0.2(4) .
C3 C4 C5 N1 178.8(2) .
C3 C4 C5 C6 1.8(4) .
C4 C5 C6 C7 -2.2(4) .
N1 C5 C6 C7 -178.9(3) .
C3 C2 C7 C6 0.8(4) .
C1 C2 C7 C6 -178.7(3) .
C5 C6 C7 C2 0.8(5) .
C12 N2 C8 C9 -0.6(4) .
N2 C8 C9 C10 -1.3(4) .
C8 C9 C10 C11 1.7(4) .
C9 C10 C11 C12 -0.5(4) .
C8 N2 C12 C11 1.9(3) .
C8 N2 C12 C12 -178.1(2) 3_656
C10 C11 C12 N2 -1.5(4) .
C10 C11 C12 C12 178.5(3) 3_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145688
