#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504909.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_4504909
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)2(C8H4O4)
_chemical_formula_sum            'C18 H18 N4 O4'
_chemical_formula_weight         354.36
_chemical_melting_point          567
_chemical_name_common            '2-aminopyridinium terephthalate 2:1'
_chemical_name_systematic
; 
 2-aminopyridinium terephthalate 2:1 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.094(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1991(8)
_cell_length_b                   14.606(2)
_cell_length_c                   11.1897(17)
_cell_measurement_temperature    100(2)
_cell_volume                     846.4(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4887
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0434
_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)+(0.0524P)²+0.2570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                1537
_reflns_number_total             1855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049622csi20041104_043911.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '567 K' was changed to '567' - the
value should be numeric and without a unit
designator.

'_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 2yn'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4504909
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
N11 N 0.6299(3) 0.29398(9) 0.94954(10) 0.0197(3) Uani 1 1 d .
H11 H 0.7563 0.2543 0.9637 0.024 Uiso 1 1 calc R
N12 N 0.6563(3) 0.26982(9) 0.74808(10) 0.0234(3) Uani 1 1 d .
H12A H 0.6046 0.2871 0.6732 0.028 Uiso 1 1 d R
H12B H 0.7965 0.2308 0.7716 0.028 Uiso 1 1 d R
C12 C 0.5437(3) 0.31192(10) 0.83438(12) 0.0195(3) Uani 1 1 d .
C13 C 0.3374(3) 0.37481(11) 0.81336(14) 0.0253(4) Uani 1 1 d .
H13 H 0.2706 0.3890 0.7337 0.030 Uiso 1 1 calc R
C14 C 0.2359(4) 0.41473(12) 0.90846(16) 0.0322(4) Uani 1 1 d .
H14 H 0.0969 0.4567 0.8946 0.039 Uiso 1 1 calc R
C15 C 0.3330(3) 0.39497(12) 1.02676(14) 0.0304(4) Uani 1 1 d .
H15 H 0.2623 0.4233 1.0929 0.036 Uiso 1 1 calc R
C16 C 0.5301(3) 0.33450(11) 1.04391(13) 0.0238(4) Uani 1 1 d .
H16 H 0.5992 0.3203 1.1232 0.029 Uiso 1 1 calc R
O21 O -0.0018(2) 0.17608(7) 1.01204(9) 0.0216(3) Uani 1 1 d .
O22 O 0.0721(2) 0.15530(8) 0.82084(9) 0.0254(3) Uani 1 1 d .
C21 C 0.3148(3) 0.06708(10) 0.96749(12) 0.0170(3) Uani 1 1 d .
C22 C 0.3243(3) 0.02565(10) 1.08002(12) 0.0188(3) Uani 1 1 d .
H22 H 0.2043 0.0431 1.1351 0.023 Uiso 1 1 calc R
C23 C 0.4932(3) 0.04060(10) 0.88807(12) 0.0184(3) Uani 1 1 d .
H23 H 0.4889 0.0685 0.8112 0.022 Uiso 1 1 calc R
C24 C 0.1138(3) 0.13810(10) 0.92973(12) 0.0179(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N11 0.0202(7) 0.0224(7) 0.0165(6) 0.0022(5) 0.0009(5) 0.0031(5)
N12 0.0263(7) 0.0300(7) 0.0136(6) 0.0026(5) -0.0009(5) 0.0075(6)
C12 0.0206(8) 0.0215(8) 0.0161(7) 0.0023(6) 0.0001(5) -0.0014(6)
C13 0.0251(9) 0.0267(8) 0.0237(7) 0.0058(6) -0.0006(6) 0.0042(6)
C14 0.0303(9) 0.0299(9) 0.0370(9) 0.0036(7) 0.0057(7) 0.0121(7)
C15 0.0368(10) 0.0299(9) 0.0258(8) -0.0016(7) 0.0108(7) 0.0070(7)
C16 0.0289(9) 0.0253(8) 0.0177(7) 0.0004(6) 0.0056(6) -0.0013(7)
O21 0.0241(6) 0.0249(6) 0.0154(5) -0.0022(4) -0.0015(4) 0.0054(4)
O22 0.0278(6) 0.0326(6) 0.0158(5) 0.0040(4) 0.0011(4) 0.0093(5)
C21 0.0189(7) 0.0166(7) 0.0149(6) -0.0018(5) -0.0018(5) -0.0033(6)
C22 0.0200(8) 0.0222(8) 0.0143(7) -0.0011(6) 0.0020(5) -0.0014(6)
C23 0.0209(8) 0.0202(8) 0.0139(6) 0.0007(5) -0.0006(5) -0.0025(6)
C24 0.0188(7) 0.0193(7) 0.0152(6) -0.0002(5) -0.0005(5) -0.0018(6)
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_1
C12 N11 C16 122.75(14) .
N12 C12 N11 118.31(14) .
N12 C12 C13 123.89(13) .
N11 C12 C13 117.81(13) .
C14 C13 C12 119.26(14) .
C13 C14 C15 121.17(16) .
C16 C15 C14 118.16(15) .
C15 C16 N11 120.84(14) .
C22 C21 C23 118.89(14) .
C22 C21 C24 121.35(13) .
C23 C21 C24 119.75(12) .
C23 C22 C21 120.42(13) 3_657
C22 C23 C21 120.69(13) 3_657
O22 C24 O21 124.70(14) .
O22 C24 C21 118.03(13) .
O21 C24 C21 117.27(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.3519(18) .
N11 C16 1.3536(19) .
N12 C12 1.3244(19) .
C12 C13 1.416(2) .
C13 C14 1.360(2) .
C14 C15 1.404(2) .
C15 C16 1.353(2) .
O21 C24 1.2709(17) .
O22 C24 1.2440(17) .
C21 C22 1.3939(19) .
C21 C23 1.395(2) .
C21 C24 1.506(2) .
C22 C23 1.380(2) 3_657
C23 C22 1.380(2) 3_657
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
N12 H12B O22 0.94 1.85 2.7969(17) 178.8 1_655
N12 H12A O21 0.89 1.92 2.8090(16) 179.3 4_665
N11 H11 O21 0.88 1.75 2.6237(17) 172.3 1_655
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
C16 N11 C12 N12 179.02(14) .
C16 N11 C12 C13 -1.0(2) .
N12 C12 C13 C14 -179.68(16) .
N11 C12 C13 C14 0.4(2) .
C12 C13 C14 C15 0.3(3) .
C13 C14 C15 C16 -0.4(3) .
C14 C15 C16 N11 -0.3(3) .
C12 N11 C16 C15 1.0(2) .
C23 C21 C22 C23 -0.2(2) 3_657
C24 C21 C22 C23 178.69(13) 3_657
C22 C21 C23 C22 0.2(2) 3_657
C24 C21 C23 C22 -178.70(13) 3_657
C22 C21 C24 O22 -162.01(14) .
C23 C21 C24 O22 16.8(2) .
C22 C21 C24 O21 17.8(2) .
C23 C21 C24 O21 -163.31(13) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145656
