#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/92/4509277.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509277
loop_
_publ_author_name
'Sarma, Bipul'
'Nath, Naba K.'
'Bhogala, Balakrishna R.'
'Nangia, Ashwini'
_publ_section_title
;
 Synthon Competition and Cooperation in Molecular Salts of Hydroxybenzoic
 Acids and Aminopyridines
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1546
_journal_paper_doi               10.1021/cg801145c
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         C7H4ClO3.C5H7N2
_chemical_formula_sum            'C12 H11 Cl N2 O3'
_chemical_formula_weight         266.68
_chemical_name_systematic
; 
 3-Aminopyridinium 3-chloro-4-hydroxybenzoate  
;
_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                 109.183(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9368(15)
_cell_length_b                   8.3774(11)
_cell_length_c                   12.6509(17)
_cell_measurement_reflns_used    1255
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.40
_cell_measurement_theta_min      2.86
_cell_volume                     1194.8(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7750
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0466
_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)+(0.0564P)²+0.4835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                1570
_reflns_number_total             2094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801145csup7.cif
_cod_data_source_block           an504_m_3-APH+.3-Cl-4-HBA-_1:1_(8)
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4509277
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
Cl1 Cl -0.10298(6) 0.22566(8) 0.47116(5) 0.0237(2) Uani 1 1 d
O1 O 0.12560(16) -0.1377(2) 0.93105(14) 0.0195(5) Uani 1 1 d
O2 O -0.06756(17) -0.1129(2) 0.83783(15) 0.0255(5) Uani 1 1 d
O3 O 0.15019(18) 0.2974(2) 0.52822(15) 0.0202(5) Uani 1 1 d
C5 C 0.1252(2) 0.2096(3) 0.6074(2) 0.0167(6) Uani 1 1 d
C2 C 0.0680(2) 0.0202(3) 0.7659(2) 0.0152(6) Uani 1 1 d
N1 N 0.0584(2) 0.6978(3) 0.07555(18) 0.0193(5) Uani 1 1 d
N2 N 0.2039(3) 0.5037(3) 0.3402(2) 0.0284(7) Uani 1 1 d
C1 C 0.0372(2) -0.0838(3) 0.8493(2) 0.0178(6) Uani 1 1 d
C8 C 0.1444(3) 0.6473(3) 0.1671(2) 0.0193(6) Uani 1 1 d
C4 C 0.0086(2) 0.1633(3) 0.5915(2) 0.0163(6) Uani 1 1 d
C12 C -0.0565(2) 0.6657(3) 0.0560(2) 0.0205(7) Uani 1 1 d
C6 C 0.2121(2) 0.1631(3) 0.7060(2) 0.0166(6) Uani 1 1 d
C3 C -0.0203(2) 0.0705(3) 0.6687(2) 0.0180(6) Uani 1 1 d
C10 C -0.0028(3) 0.5215(3) 0.2279(2) 0.0220(7) Uani 1 1 d
C7 C 0.1843(2) 0.0693(3) 0.7832(2) 0.0162(6) Uani 1 1 d
C9 C 0.1180(2) 0.5568(3) 0.2475(2) 0.0194(6) Uani 1 1 d
C11 C -0.0878(3) 0.5758(3) 0.1327(2) 0.0225(7) Uani 1 1 d
H12 H -0.109(2) 0.708(3) -0.012(2) 0.011(7) Uiso 1 1 d
H7 H 0.247(2) 0.040(3) 0.850(2) 0.013(7) Uiso 1 1 d
H8 H 0.224(3) 0.676(3) 0.176(2) 0.022(8) Uiso 1 1 d
H3 H -0.102(3) 0.040(3) 0.654(2) 0.016(7) Uiso 1 1 d
H6 H 0.296(2) 0.198(3) 0.720(2) 0.015(7) Uiso 1 1 d
H10 H -0.019(3) 0.462(3) 0.286(2) 0.026(8) Uiso 1 1 d
H11 H -0.168(3) 0.555(4) 0.121(2) 0.032(9) Uiso 1 1 d
H3A H 0.225(4) 0.324(4) 0.551(3) 0.059(12) Uiso 1 1 d
H2B H 0.275(3) 0.532(4) 0.346(2) 0.028(9) Uiso 1 1 d
H1 H 0.082(3) 0.767(4) 0.017(3) 0.039(9) Uiso 1 1 d
H2A H 0.183(3) 0.458(4) 0.399(3) 0.032(9) 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'
Cl Cl 0.1484 0.1585 '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
C5 O3 H3A 110(2)
O3 C5 C6 122.3(3)
O3 C5 C4 119.8(2)
C6 C5 C4 117.9(3)
C7 C2 C3 118.3(3)
C7 C2 C1 121.4(2)
C3 C2 C1 120.4(2)
C12 N1 C8 123.0(3)
C12 N1 H1 118.3(18)
C8 N1 H1 118.7(18)
C9 N2 H2B 115(2)
C9 N2 H2A 120(2)
H2B N2 H2A 124(3)
O2 C1 O1 123.6(3)
O2 C1 C2 120.2(2)
O1 C1 C2 116.2(2)
N1 C8 C9 120.9(3)
N1 C8 H8 118.4(17)
C9 C8 H8 120.7(17)
C3 C4 C5 121.7(2)
C3 C4 Cl1 119.4(2)
C5 C4 Cl1 118.9(2)
N1 C12 C11 118.6(3)
N1 C12 H12 115.3(16)
C11 C12 H12 126.0(16)
C7 C6 C5 120.9(3)
C7 C6 H6 120.0(15)
C5 C6 H6 119.1(15)
C4 C3 C2 120.2(3)
C4 C3 H3 119.1(16)
C2 C3 H3 120.8(16)
C11 C10 C9 120.2(3)
C11 C10 H10 124.7(17)
C9 C10 H10 115.1(17)
C6 C7 C2 121.1(2)
C6 C7 H7 117.9(16)
C2 C7 H7 121.0(16)
N2 C9 C8 121.7(3)
N2 C9 C10 121.5(3)
C8 C9 C10 116.8(3)
C10 C11 C12 120.5(3)
C10 C11 H11 120.2(19)
C12 C11 H11 119.3(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.741(2)
O1 C1 1.292(3)
O2 C1 1.236(3)
O3 C5 1.353(3)
O3 H3A 0.87(4)
C5 C6 1.390(4)
C5 C4 1.394(4)
C2 C7 1.395(4)
C2 C3 1.396(4)
C2 C1 1.503(4)
N1 C12 1.338(3)
N1 C8 1.339(3)
N1 H1 1.05(3)
N2 C9 1.354(4)
N2 H2B 0.86(3)
N2 H2A 0.94(3)
C8 C9 1.385(4)
C8 H8 0.95(3)
C4 C3 1.378(4)
C12 C11 1.374(4)
C12 H12 0.95(3)
C6 C7 1.378(4)
C6 H6 1.00(3)
C3 H3 0.96(3)
C10 C11 1.373(4)
C10 C9 1.412(4)
C10 H10 0.96(3)
C7 H7 0.96(3)
C11 H11 0.94(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146892
