#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/11/4501190.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_4501190
loop_
_publ_author_name
'Nath, Naba K.'
'Kumar, S. Sudalai'
'Nangia, Ashwini'
_publ_section_title
;
 Neutral and Zwitterionic Polymorphs of 2-(p-Tolylamino)nicotinic Acid
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4594
_journal_paper_doi               10.1021/cg200853u
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.2565(16)
_cell_length_b                   10.7542(15)
_cell_length_c                   14.769(3)
_cell_measurement_reflns_used    391
_cell_measurement_temperature    100
_cell_measurement_theta_max      34.7532
_cell_measurement_theta_min      3.3682
_cell_volume                     2264.3(6)
_computing_cell_refinement
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
 (compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
 (compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
 (compiled Sep 15 2009,11:49:04)
;
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
 1 omega 16.00 66.00 1.0000 5.0000
 omega____ theta____ kappa____ phi______ frames
 - 32.5154 77.0000 -180.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.005861633
_diffrn_orient_matrix_UB_12      -0.0215246834
_diffrn_orient_matrix_UB_13      -0.0438099349
_diffrn_orient_matrix_UB_21      0.0057287707
_diffrn_orient_matrix_UB_22      0.0448767729
_diffrn_orient_matrix_UB_23      -0.0208979537
_diffrn_orient_matrix_UB_31      0.0655730114
_diffrn_orient_matrix_UB_32      -0.005683902
_diffrn_orient_matrix_UB_33      -0.0020945775
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10798
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.89591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
 (compiled Sep 15 2009,11:49:04)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0510P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2306
_reflns_number_total             4319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200853u_si_002.cif
_cod_data_source_block           Form-II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               4501190
loop_
_symmetry_equiv_pos_as_xyz
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, z'
'x-1/2, y, -z-1/2'
'-x, y+1/2, -z+1/2'
'x, -y-1/2, z-1/2'
'-x+1/2, -y, 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
C2 C 0.16998(8) 0.79818(12) 1.01265(9) 0.0154(3) Uani 1 1 d .
O1 O 0.33332(6) 0.81392(9) 1.01808(7) 0.0237(2) Uani 1 1 d .
N2 N 0.08905(7) 0.65684(11) 0.91215(9) 0.0200(3) Uani 1 1 d .
N1 N 0.00111(6) 0.79094(10) 1.00302(8) 0.0152(2) Uani 1 1 d .
O2 O 0.27368(6) 0.65280(10) 0.94177(8) 0.0273(3) Uani 1 1 d .
C6 C 0.08559(8) 0.74847(12) 0.97531(9) 0.0147(3) Uani 1 1 d .
C10 C -0.13341(8) 0.48553(13) 0.77002(10) 0.0184(3) Uani 1 1 d .
C5 C -0.00191(9) 0.88072(12) 1.06623(10) 0.0175(3) Uani 1 1 d .
H5 H -0.0605 0.9087 1.0850 0.021 Uiso 1 1 calc R
C1 C 0.26304(8) 0.74730(13) 0.98664(10) 0.0175(3) Uani 1 1 d .
C7 C 0.01254(8) 0.60178(12) 0.86504(9) 0.0159(3) Uani 1 1 d .
C3 C 0.16337(8) 0.89146(12) 1.07658(10) 0.0182(3) Uani 1 1 d .
H3 H 0.2177 0.9261 1.1007 0.022 Uiso 1 1 calc R
C9 C -0.12363(8) 0.61402(13) 0.76935(10) 0.0183(3) Uani 1 1 d .
H9 H -0.1664 0.6621 0.7372 0.022 Uiso 1 1 calc R
C8 C -0.05110(8) 0.67199(12) 0.81586(10) 0.0178(3) Uani 1 1 d .
H8 H -0.0452 0.7581 0.8140 0.021 Uiso 1 1 calc R
C11 C -0.06777(9) 0.41644(13) 0.81799(11) 0.0215(3) Uani 1 1 d .
H11 H -0.0724 0.3302 0.8185 0.026 Uiso 1 1 calc R
C12 C 0.00468(9) 0.47357(12) 0.86529(10) 0.0200(3) Uani 1 1 d .
H12 H 0.0478 0.4256 0.8971 0.024 Uiso 1 1 calc R
C4 C 0.07627(8) 0.93394(12) 1.10507(10) 0.0192(3) Uani 1 1 d .
H4 H 0.0709 0.9959 1.1487 0.023 Uiso 1 1 calc R
C13 C -0.21343(9) 0.42285(15) 0.72084(12) 0.0289(4) Uani 1 1 d .
H13C H -0.2703 0.4337 0.7547 0.043 Uiso 1 1 calc R
H13B H -0.2003 0.3357 0.7147 0.043 Uiso 1 1 calc R
H13A H -0.2206 0.4593 0.6619 0.043 Uiso 1 1 calc R
H2 H 0.1441(11) 0.6251(15) 0.9069(11) 0.032(4) Uiso 1 1 d .
H1 H 0.3945(16) 0.771(2) 1.0126(16) 0.079(7) 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
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'
C C 0.0033 0.0016 '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
C2 C3 H3 119.8
C2 C3 C4 120.48(12)
O1 C1 C2 112.84(12)
N2 C6 C2 120.44(11)
N1 C6 C2 120.50(12)
N1 C6 N2 119.05(11)
N1 C5 H5 117.9
N1 C5 C4 124.17(12)
O2 C1 C2 123.85(11)
O2 C1 O1 123.30(11)
C6 C2 C1 120.99(12)
C6 N2 C7 127.60(11)
C6 N2 H2 112.6(11)
C10 C9 H9 119.4
C10 C9 C8 121.18(12)
C10 C11 H11 119.3
C10 C11 C12 121.37(13)
C10 C13 H13C 109.5
C10 C13 H13B 109.5
C10 C13 H13A 109.5
C5 N1 C6 118.80(10)
C5 C4 C3 117.43(13)
C5 C4 H4 121.3
C1 O1 H1 112.7(13)
C7 N2 H2 119.4(11)
C7 C8 C9 120.13(12)
C7 C8 H8 119.9
C7 C12 C11 119.95(13)
C7 C12 H12 120.0
C3 C2 C6 118.61(11)
C3 C2 C1 120.35(11)
C3 C4 H4 121.3
C9 C10 C11 117.91(12)
C9 C10 C13 121.08(13)
C9 C8 H8 119.9
C8 C7 N2 122.10(12)
C8 C9 H9 119.4
C11 C10 C13 121.01(13)
C11 C12 H12 120.0
C12 C7 N2 118.40(12)
C12 C7 C8 119.43(12)
C12 C11 H11 119.3
C4 C5 H5 117.9
C4 C3 H3 119.8
H13C C13 H13B 109.5
H13C C13 H13A 109.5
H13B C13 H13A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 C6 1.4273(16)
C2 C1 1.4856(17)
C2 C3 1.3808(19)
O1 C1 1.3163(15)
O1 H1 0.99(2)
N2 C6 1.3577(18)
N2 C7 1.4230(16)
N2 H2 0.859(15)
N1 C6 1.3516(15)
N1 C5 1.3438(17)
O2 C1 1.2227(17)
C10 C9 1.3889(18)
C10 C11 1.3891(19)
C10 C13 1.5111(19)
C5 H5 0.9300
C5 C4 1.3779(18)
C7 C8 1.3858(18)
C7 C12 1.3834(18)
C3 H3 0.9300
C3 C4 1.3884(17)
C9 H9 0.9300
C9 C8 1.3891(18)
C8 H8 0.9300
C11 H11 0.9300
C11 C12 1.3901(19)
C12 H12 0.9300
C4 H4 0.9300
C13 H13C 0.9600
C13 H13B 0.9600
C13 H13A 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4458841
2 PubChem 5298375
