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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507333.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_4507333
loop_
_publ_author_name
'Goswami, Pramod Kumar'
'Thaimattam, Ram'
'Ramanan, Arunachalam'
_publ_section_title
;
 Multiple Crystal Forms ofp-Aminosalicylic Acid: Salts, Salt Co-Crystal
 Hydrate, Co-Crystals, and Co-Crystal Polymorphs
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              360
_journal_paper_doi               10.1021/cg3015332
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C7 H6 N O3, C5 H7 N2'
_chemical_formula_sum            'C12 H13 N3 O3'
_chemical_formula_weight         247.25
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.3978(19)
_cell_length_b                   12.5471(17)
_cell_length_c                   13.8797(19)
_cell_measurement_reflns_used    1876
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.87
_cell_volume                     2333.2(6)
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20730
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.217
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0638
_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)+(0.0444P)²+2.1569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                1876
_reflns_number_total             2050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015332_si_003.cif
_cod_data_source_block           solid3
_cod_database_code               4507333
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 1.10056(12) 0.55542(14) 0.06449(12) 0.0239(4) Uani 1 1 d .
O2 O 1.06021(13) 0.40000(13) 0.13148(13) 0.0267(5) Uani 1 1 d .
O3 O 0.90801(15) 0.38483(14) 0.23801(15) 0.0324(5) Uani 1 1 d .
N1 N 0.70675(18) 0.6916(2) 0.29149(18) 0.0290(6) Uani 1 1 d .
N2 N 0.25811(16) 0.45361(17) 0.99415(14) 0.0230(5) Uani 1 1 d .
N3 N 0.52306(17) 0.3239(2) 0.90235(17) 0.0273(5) Uani 1 1 d .
C1 C 1.04371(18) 0.49833(19) 0.11533(17) 0.0197(5) Uani 1 1 d .
C2 C 0.95554(17) 0.54909(19) 0.16123(17) 0.0197(5) Uani 1 1 d .
C3 C 0.89034(18) 0.48999(19) 0.22030(17) 0.0203(6) Uani 1 1 d .
C4 C 0.80724(18) 0.5365(2) 0.26229(17) 0.0220(6) Uani 1 1 d .
H7 H 0.7647 0.4955 0.3002 0.026 Uiso 1 1 calc R
C5 C 0.78683(18) 0.64500(19) 0.24806(17) 0.0204(5) Uani 1 1 d .
C6 C 0.85284(18) 0.70523(19) 0.19093(17) 0.0220(6) Uani 1 1 d .
H8 H 0.8414 0.7776 0.1818 0.026 Uiso 1 1 calc R
C7 C 0.93393(18) 0.65764(19) 0.14866(17) 0.0209(6) Uani 1 1 d .
H9 H 0.9760 0.6987 0.1104 0.025 Uiso 1 1 calc R
C8 C 0.32364(19) 0.5139(2) 0.94579(18) 0.0252(6) Uani 1 1 d .
H12 H 0.3084 0.5850 0.9340 0.030 Uiso 1 1 calc R
C9 C 0.41196(19) 0.4738(2) 0.91346(18) 0.0249(6) Uani 1 1 d .
H13 H 0.4564 0.5174 0.8803 0.030 Uiso 1 1 calc R
C10 C 0.43555(18) 0.3661(2) 0.93048(17) 0.0208(6) Uani 1 1 d .
C11 C 0.36495(19) 0.3045(2) 0.98100(18) 0.0228(6) Uani 1 1 d .
H10 H 0.3774 0.2329 0.9935 0.027 Uiso 1 1 calc R
C12 C 0.27836(19) 0.3505(2) 1.01142(18) 0.0243(6) Uani 1 1 d .
H11 H 0.2321 0.3095 1.0450 0.029 Uiso 1 1 calc R
H1 H 0.968(3) 0.376(3) 0.200(3) 0.061(11) Uiso 1 1 d .
H2 H 0.666(2) 0.650(2) 0.328(2) 0.037(8) Uiso 1 1 d .
H3 H 0.688(2) 0.753(3) 0.276(2) 0.033(8) Uiso 1 1 d .
H4 H 0.194(2) 0.487(3) 1.020(2) 0.055(10) Uiso 1 1 d .
H5 H 0.563(3) 0.363(3) 0.867(3) 0.057(11) Uiso 1 1 d .
H6 H 0.531(2) 0.253(3) 0.903(2) 0.040(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O3 H1 99(2)
C5 N1 H2 118.0(19)
C5 N1 H3 121(2)
H2 N1 H3 120(3)
C8 N2 C12 120.1(2)
C8 N2 H4 119.9(19)
C12 N2 H4 120.0(19)
C10 N3 H5 119(2)
C10 N3 H6 119(2)
H5 N3 H6 119(3)
O1 C1 O2 123.0(2)
O1 C1 C2 118.5(2)
O2 C1 C2 118.5(2)
C7 C2 C3 117.1(2)
C7 C2 C1 121.8(2)
C3 C2 C1 121.1(2)
O3 C3 C4 118.1(2)
O3 C3 C2 120.4(2)
C4 C3 C2 121.4(2)
C3 C4 C5 120.4(2)
C3 C4 H7 119.8
C5 C4 H7 119.8
N1 C5 C4 120.5(2)
N1 C5 C6 120.9(2)
C4 C5 C6 118.6(2)
C7 C6 C5 120.3(2)
C7 C6 H8 119.8
C5 C6 H8 119.8
C6 C7 C2 122.2(2)
C6 C7 H9 118.9
C2 C7 H9 118.9
N2 C8 C9 121.8(2)
N2 C8 H12 119.1
C9 C8 H12 119.1
C8 C9 C10 119.6(2)
C8 C9 H13 120.2
C10 C9 H13 120.2
N3 C10 C9 121.7(2)
N3 C10 C11 120.9(2)
C9 C10 C11 117.4(2)
C12 C11 C10 119.5(2)
C12 C11 H10 120.2
C10 C11 H10 120.2
N2 C12 C11 121.6(2)
N2 C12 H11 119.2
C11 C12 H11 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.261(3)
O2 C1 1.273(3)
O3 C3 1.363(3)
O3 H1 0.96(4)
N1 C5 1.363(3)
N1 H2 0.91(3)
N1 H3 0.84(3)
N2 C8 1.339(3)
N2 C12 1.344(3)
N2 H4 1.02(3)
N3 C10 1.344(3)
N3 H5 0.87(4)
N3 H6 0.89(4)
C1 C2 1.486(3)
C2 C7 1.403(3)
C2 C3 1.409(3)
C3 C4 1.386(3)
C4 C5 1.402(3)
C4 H7 0.9300
C5 C6 1.408(3)
C6 C7 1.372(3)
C6 H8 0.9300
C7 H9 0.9300
C8 C9 1.362(4)
C8 H12 0.9300
C9 C10 1.408(4)
C9 H13 0.9300
C10 C11 1.409(4)
C11 C12 1.363(4)
C11 H10 0.9300
C12 H11 0.9300
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
O1 C1 C2 C7 0.6(3)
O2 C1 C2 C7 178.4(2)
O1 C1 C2 C3 -178.8(2)
O2 C1 C2 C3 -0.9(3)
C7 C2 C3 O3 -178.2(2)
C1 C2 C3 O3 1.2(4)
C7 C2 C3 C4 1.5(4)
C1 C2 C3 C4 -179.1(2)
O3 C3 C4 C5 178.6(2)
C2 C3 C4 C5 -1.0(4)
C3 C4 C5 N1 -178.1(2)
C3 C4 C5 C6 -0.4(4)
N1 C5 C6 C7 179.1(2)
C4 C5 C6 C7 1.4(4)
C5 C6 C7 C2 -1.0(4)
C3 C2 C7 C6 -0.4(4)
C1 C2 C7 C6 -179.8(2)
C12 N2 C8 C9 -0.4(4)
N2 C8 C9 C10 0.3(4)
C8 C9 C10 N3 -178.0(2)
C8 C9 C10 C11 0.0(4)
N3 C10 C11 C12 177.8(2)
C9 C10 C11 C12 -0.3(4)
C8 N2 C12 C11 0.1(4)
C10 C11 C12 N2 0.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146384
