#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504908.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_4504908
loop_
_publ_author_name
'Bis, Joanna A.'
'Zaworotko, Michael J.'
_publ_section_title
;
 The 2-Aminopyridinium-carboxylate Supramolecular Heterosynthon:  A
 Robust Motif for Generation of Multiple-Component Crystals
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1169
_journal_paper_doi               10.1021/cg049622c
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         (C5H7N2)(C8H5O4)
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.25
_chemical_melting_point          472.5(15)
_chemical_name_common            '2-aminopyridinium isophthalate 1:1'
_chemical_name_systematic
; 
 2-aminopyridinium isophthalate 1:1 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.831(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5619(13)
_cell_length_b                   8.0768(9)
_cell_length_c                   12.2356(13)
_cell_measurement_temperature    100(2)
_cell_volume                     1167.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5678
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0331
_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)+(0.0658P)²+0.3057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                1881
_reflns_number_total             2056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049622csi20041104_043900.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '471-474 K' was changed to
'472.5(15)' - the average value was taken and precision was
estimated.

'_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constra' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_Hall     'P 2ybc'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4504908
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
N11 N 0.54802(8) 0.30133(12) 0.48850(8) 0.0166(2) Uani 1 1 d .
H11 H 0.4949 0.2346 0.4946 0.020 Uiso 1 1 calc R
N12 N 0.46318(9) 0.28855(14) 0.28960(9) 0.0226(3) Uani 1 1 d .
H12A H 0.4097 0.2302 0.3003 0.027 Uiso 1 1 d R
H12B H 0.4538 0.3290 0.2217 0.027 Uiso 1 1 d R
C12 C 0.54633(10) 0.34572(15) 0.38151(10) 0.0174(3) Uani 1 1 d .
C13 C 0.63430(10) 0.44935(16) 0.37404(11) 0.0209(3) Uani 1 1 d .
H13 H 0.6374 0.4799 0.3002 0.025 Uiso 1 1 calc R
C14 C 0.71457(10) 0.50528(16) 0.47288(11) 0.0226(3) Uani 1 1 d .
H14 H 0.7730 0.5761 0.4676 0.027 Uiso 1 1 calc R
C15 C 0.71176(10) 0.45916(16) 0.58252(11) 0.0226(3) Uani 1 1 d .
H15 H 0.7667 0.4994 0.6517 0.027 Uiso 1 1 calc R
C16 C 0.62831(10) 0.35557(16) 0.58676(10) 0.0200(3) Uani 1 1 d .
H16 H 0.6262 0.3204 0.6601 0.024 Uiso 1 1 calc R
O21 O -0.13232(7) 0.68329(11) 0.32754(7) 0.0217(2) Uani 1 1 d .
H21 H -0.1865 0.6570 0.2636 0.026 Uiso 1 1 d R
O22 O -0.06627(7) 0.81998(12) 0.20524(7) 0.0227(2) Uani 1 1 d .
O23 O 0.30493(6) 1.09782(11) 0.35499(7) 0.0195(2) Uani 1 1 d .
O24 O 0.39891(7) 1.10806(11) 0.54513(7) 0.0192(2) Uani 1 1 d .
C21 C 0.04239(10) 0.82400(15) 0.40682(10) 0.0167(3) Uani 1 1 d .
C22 C 0.12852(10) 0.91564(15) 0.38818(10) 0.0167(3) Uani 1 1 d .
H22 H 0.1239 0.9418 0.3110 0.020 Uiso 1 1 calc R
C23 C 0.22090(9) 0.96923(15) 0.48064(10) 0.0160(3) Uani 1 1 d .
C24 C 0.22573(10) 0.93049(15) 0.59347(10) 0.0188(3) Uani 1 1 d .
H24 H 0.2879 0.9676 0.6578 0.023 Uiso 1 1 calc R
C25 C 0.14044(10) 0.83828(16) 0.61220(10) 0.0207(3) Uani 1 1 d .
H25 H 0.1448 0.8122 0.6893 0.025 Uiso 1 1 calc R
C26 C 0.04897(10) 0.78382(16) 0.51944(10) 0.0192(3) Uani 1 1 d .
H26 H -0.0088 0.7195 0.5326 0.023 Uiso 1 1 calc R
C27 C -0.05613(10) 0.77641(15) 0.30287(10) 0.0178(3) Uani 1 1 d .
C28 C 0.31445(9) 1.06572(14) 0.45918(10) 0.0159(3) Uani 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
C12 N11 C16 122.48(11)
N12 C12 N11 118.46(11)
N12 C12 C13 123.87(11)
N11 C12 C13 117.66(11)
C14 C13 C12 119.89(11)
C13 C14 C15 120.61(11)
C16 C15 C14 118.07(11)
N11 C16 C15 121.24(11)
C26 C21 C22 119.88(11)
C26 C21 C27 122.52(11)
C22 C21 C27 117.58(11)
C23 C22 C21 120.94(11)
C22 C23 C24 118.69(11)
C22 C23 C28 120.40(10)
C24 C23 C28 120.91(10)
C25 C24 C23 120.46(11)
C26 C25 C24 120.54(11)
C25 C26 C21 119.47(11)
O22 C27 O21 123.08(11)
O22 C27 C21 123.05(11)
O21 C27 C21 113.87(10)
O24 C28 O23 123.32(10)
O24 C28 C23 118.71(10)
O23 C28 C23 117.96(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N11 C12 1.3506(15)
N11 C16 1.3535(16)
N12 C12 1.3311(16)
C12 C13 1.4137(17)
C13 C14 1.3623(18)
C14 C15 1.4042(18)
C15 C16 1.3558(18)
O21 C27 1.3299(15)
O22 C27 1.2099(14)
O23 C28 1.2662(14)
O24 C28 1.2616(14)
C21 C26 1.3905(17)
C21 C22 1.3921(17)
C21 C27 1.4930(16)
C22 C23 1.3867(16)
C23 C24 1.3967(17)
C23 C28 1.5056(16)
C24 C25 1.3862(17)
C25 C26 1.3845(17)
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
N11 H11 O24 0.88 1.84 2.7029(13) 166.0 1_545
N11 H11 O23 0.88 2.66 3.3631(13) 137.8 1_545
N12 H12A O23 0.87 1.98 2.8362(13) 169.6 1_545
N12 H12B O24 0.86 2.10 2.9424(13) 167.0 4_575
O21 H21 O23 0.87 1.76 2.6231(11) 173.4 2_545
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
C16 N11 C12 N12 -178.98(11)
C16 N11 C12 C13 1.67(17)
N12 C12 C13 C14 178.45(11)
N11 C12 C13 C14 -2.23(17)
C12 C13 C14 C15 0.86(19)
C13 C14 C15 C16 1.13(19)
C12 N11 C16 C15 0.34(18)
C14 C15 C16 N11 -1.76(18)
C26 C21 C22 C23 -0.60(18)
C27 C21 C22 C23 177.81(10)
C21 C22 C23 C24 -0.45(18)
C21 C22 C23 C28 178.93(10)
C22 C23 C24 C25 0.89(18)
C28 C23 C24 C25 -178.49(11)
C23 C24 C25 C26 -0.29(19)
C24 C25 C26 C21 -0.77(19)
C22 C21 C26 C25 1.21(18)
C27 C21 C26 C25 -177.12(11)
C26 C21 C27 O22 174.97(11)
C22 C21 C27 O22 -3.39(18)
C26 C21 C27 O21 -4.32(17)
C22 C21 C27 O21 177.32(10)
C22 C23 C28 O24 -177.81(10)
C24 C23 C28 O24 1.56(16)
C22 C23 C28 O23 1.02(16)
C24 C23 C28 O23 -179.61(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145655
