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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/4/50/70/4507051.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_4507051
loop_
_publ_author_name
'Stilinović, Vladimir'
'Kaitner, Branko'
_publ_section_title
;
 Salts and Co-Crystals of Gentisic Acid with Pyridine Derivatives: The
 Effect of Proton Transfer on the Crystal Packing (and Vice Versa)
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5763
_journal_paper_doi               10.1021/cg301267h
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C7 H6 O4, C6 H5 N O2'
_chemical_formula_sum            'C13 H11 N O6'
_chemical_formula_weight         277.23
_chemical_name_systematic
;
nicotinic acid - 2,5-dihydroxybenzoic acid
;
_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_date             2012-07-10T15:44:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.97(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.082(2)
_cell_length_b                   7.7361(12)
_cell_length_c                   13.992(2)
_cell_measurement_reflns_used    173
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      52.0
_cell_measurement_theta_min      4.6
_cell_volume                     1204.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4430
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.97
_diffrn_standards_number         27
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.342
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.1091
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3352
_refine_ls_wR_factor_ref         0.3447
_reflns_number_gt                1436
_reflns_number_total             2083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301267h_si_002.cif
_cod_data_source_block           14_gentH
_cod_original_cell_volume        1204.0(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4507051
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
C12 C 0.2036(5) 0.0670(7) 0.2662(4) 0.0424(13) Uani 1 1 d .
H12 H 0.2459 0.0395 0.2251 0.051 Uiso 1 1 calc R
C10 C 0.1763(4) 0.0493(6) 0.4255(4) 0.0373(12) Uani 1 1 d .
H10 H 0.2009 0.0085 0.4932 0.045 Uiso 1 1 calc R
C13 C 0.0086(4) 0.2117(6) 0.4518(4) 0.0377(12) Uani 1 1 d .
O5 O -0.0903(3) 0.2889(5) 0.4043(3) 0.0529(11) Uani 1 1 d .
O6 O 0.0571(3) 0.1814(5) 0.5460(2) 0.0484(11) Uani 1 1 d .
C11 C 0.2405(4) 0.0038(7) 0.3667(4) 0.0412(12) Uani 1 1 d .
H11 H 0.3073 -0.068 0.3938 0.049 Uiso 1 1 calc R
C9 C 0.0758(4) 0.1548(6) 0.3857(3) 0.0338(11) Uani 1 1 d .
C8 C 0.0420(4) 0.2121(7) 0.2845(3) 0.0386(12) Uani 1 1 d .
H8 H -0.0258 0.2815 0.255 0.046 Uiso 1 1 calc R
N1 N 0.1058(4) 0.1686(5) 0.2292(3) 0.0392(11) Uani 1 1 d .
H1N H 0.0833 0.2073 0.1669 0.047 Uiso 1 1 calc R
C6 C 0.7175(4) 0.4598(7) 0.6756(4) 0.0406(12) Uani 1 1 d .
H6 H 0.78 0.3801 0.6935 0.049 Uiso 1 1 calc R
O3 O 0.5494(3) 0.7589(6) 0.4631(3) 0.0581(12) Uani 1 1 d .
H1O H 0.5942 0.7408 0.4327 0.087 Uiso 1 1 calc R
C4 C 0.5674(5) 0.6073(8) 0.7141(4) 0.0538(16) Uani 1 1 d .
H4 H 0.5272 0.6261 0.7579 0.065 Uiso 1 1 calc R
C7 C 0.7400(4) 0.5097(7) 0.5084(4) 0.0402(12) Uani 1 1 d .
C5 C 0.6614(4) 0.4883(8) 0.7426(4) 0.0458(14) Uani 1 1 d .
C3 C 0.5330(4) 0.6976(8) 0.6220(4) 0.0493(15) Uani 1 1 d .
H3 H 0.4719 0.7793 0.6056 0.059 Uiso 1 1 calc R
C2 C 0.5887(4) 0.6676(7) 0.5537(4) 0.0427(13) Uani 1 1 d .
O4 O 0.6903(3) 0.3999(6) 0.8341(3) 0.0617(13) Uani 1 1 d .
H2O H 0.7543 0.3492 0.848 0.093 Uiso 1 1 calc R
C1 C 0.6829(4) 0.5478(6) 0.5810(4) 0.0386(12) Uani 1 1 d .
O1 O 0.8280(4) 0.3952(6) 0.5425(3) 0.0549(12) Uani 1 1 d .
H3O H 0.8538 0.3766 0.4973 0.13(4) Uiso 1 1 calc R
O2 O 0.7096(3) 0.5772(6) 0.4219(3) 0.0567(11) 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 0 '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 0.006 '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
N1 C12 C11 118.8(4)
N1 C12 H12 120.6
C11 C12 H12 120.6
C11 C10 C9 121.3(4)
C11 C10 H10 119.4
C9 C10 H10 119.4
O6 C13 O5 127.2(4)
O6 C13 C9 116.8(4)
O5 C13 C9 115.9(4)
C10 C11 C12 118.8(5)
C10 C11 H11 120.6
C12 C11 H11 120.6
C8 C9 C10 117.5(4)
C8 C9 C13 121.1(4)
C10 C9 C13 121.3(4)
N1 C8 C9 120.4(4)
N1 C8 H8 119.8
C9 C8 H8 119.8
C8 N1 C12 123.1(4)
C8 N1 H1N 118.4
C12 N1 H1N 118.4
C5 C6 C1 121.5(5)
C5 C6 H6 119.2
C1 C6 H6 119.2
C2 O3 H1O 109.5
C3 C4 C5 121.0(5)
C3 C4 H4 119.5
C5 C4 H4 119.5
O2 C7 O1 121.8(4)
O2 C7 C1 123.7(5)
O1 C7 C1 114.5(4)
O4 C5 C6 122.9(5)
O4 C5 C4 118.6(5)
C6 C5 C4 118.5(5)
C4 C3 C2 120.6(5)
C4 C3 H3 119.7
C2 C3 H3 119.7
O3 C2 C3 117.9(5)
O3 C2 C1 123.1(4)
C3 C2 C1 119.0(5)
C5 O4 H2O 109.5
C6 C1 C2 119.4(4)
C6 C1 C7 120.7(5)
C2 C1 C7 119.8(5)
C7 O1 H3O 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C12 N1 1.343(7)
C12 C11 1.388(7)
C12 H12 0.93
C10 C11 1.379(7)
C10 C9 1.387(7)
C10 H10 0.93
C13 O6 1.239(6)
C13 O5 1.267(6)
C13 C9 1.515(6)
C11 H11 0.93
C9 C8 1.384(6)
C8 N1 1.332(6)
C8 H8 0.93
N1 H1N 0.86
C6 C5 1.372(7)
C6 C1 1.400(7)
C6 H6 0.93
O3 C2 1.364(7)
O3 H1O 0.82
C4 C3 1.380(8)
C4 C5 1.393(8)
C4 H4 0.93
C7 O2 1.235(6)
C7 O1 1.322(6)
C7 C1 1.463(7)
C5 O4 1.371(7)
C3 C2 1.386(7)
C3 H3 0.93
C2 C1 1.401(7)
O4 H2O 0.82
O1 H3O 0.82
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146293
