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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/4/50/70/4507058.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_4507058
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, 2(C6 H4 N2)'
_chemical_formula_sum            'C19 H14 N4 O4'
_chemical_formula_weight         362.34
_chemical_name_systematic
;
4-cyanopyridine - - 2,5-dihydroxybenzoic acid (2:1)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-10T18:03:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.733(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.126(4)
_cell_length_b                   12.2129(12)
_cell_length_c                   12.3844(10)
_cell_measurement_reflns_used    79
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      52.0
_cell_measurement_theta_min      4.6
_cell_volume                     1795.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3319
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.83
_diffrn_standards_number         27
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.085
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.022
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0343
_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)+(0.0416P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                1199
_reflns_number_total             2141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301267h_si_002.cif
_cod_data_source_block           (20)2_gentH
_cod_original_sg_symbol_Hall     'C -2yc '
_cod_original_sg_symbol_H-M      'C c '
_cod_database_code               4507058
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
H2O H 0.448(4) 0.320(4) -0.224(4) 0.106(18) Uiso 1 1 d .
H3O H 0.290(4) 0.320(4) 0.266(4) 0.099(17) Uiso 1 1 d .
C6 C 0.3756(4) 0.2720(3) 0.0046(3) 0.0655(12) Uani 1 1 d .
H6 H 0.3753 0.3437 0.0301 0.079 Uiso 1 1 calc R
N1 N 0.2498(3) 0.3391(3) 0.3935(3) 0.0687(10) Uani 1 1 d .
C9 C 0.1756(4) 0.2706(4) 0.5438(3) 0.0755(14) Uani 1 1 d .
H9 H 0.1523 0.2113 0.5806 0.091 Uiso 1 1 calc R
C7 C 0.3149(3) 0.2076(4) 0.1747(3) 0.0655(12) Uani 1 1 d .
O2 O 0.2922(3) 0.1347(2) 0.2341(2) 0.0889(10) Uani 1 1 d .
O1 O 0.3110(3) 0.3128(2) 0.2018(3) 0.0789(10) Uani 1 1 d .
C2 C 0.3494(4) 0.0800(3) 0.0280(3) 0.0695(13) Uani 1 1 d .
C4 C 0.4056(4) 0.1468(3) -0.1347(3) 0.0783(14) Uani 1 1 d .
H4 H 0.424 0.1335 -0.2029 0.094 Uiso 1 1 calc R
O3 O 0.3220(3) -0.0080(2) 0.0859(2) 0.1015(11) Uani 1 1 d .
H1O H 0.3076 0.0131 0.1443 0.152 Uiso 1 1 calc R
O4 O 0.4306(3) 0.3409(2) -0.1553(3) 0.1022(13) Uani 1 1 d .
C13 C 0.1271(4) 0.3952(4) 0.6808(4) 0.0807(13) Uani 1 1 d .
C11 C 0.2093(4) 0.4608(3) 0.5307(3) 0.0759(12) Uani 1 1 d .
H11 H 0.2094 0.5317 0.5582 0.091 Uiso 1 1 calc R
N2 N 0.0885(4) 0.4158(3) 0.7571(3) 0.1081(15) Uani 1 1 d .
C1 C 0.3478(3) 0.1880(3) 0.0679(3) 0.0600(11) Uani 1 1 d .
C12 C 0.2468(4) 0.4389(3) 0.4365(3) 0.0783(14) Uani 1 1 d .
H12 H 0.2719 0.4973 0.3998 0.094 Uiso 1 1 calc R
C8 C 0.2151(4) 0.2559(4) 0.4482(3) 0.0758(14) Uani 1 1 d .
H8 H 0.2178 0.1854 0.4206 0.091 Uiso 1 1 calc R
C10 C 0.1716(4) 0.3743(4) 0.5831(3) 0.0676(11) Uani 1 1 d .
C3 C 0.3798(4) 0.0607(3) -0.0717(3) 0.0805(14) Uani 1 1 d .
H3 H 0.3829 -0.0108 -0.0968 0.097 Uiso 1 1 calc R
C5 C 0.4038(4) 0.2522(3) -0.0958(3) 0.0700(12) Uani 1 1 d .
C14 C 0.0116(5) 0.0949(4) 0.1103(4) 0.0954(17) Uani 1 1 d .
H14 H 0.004 0.0355 0.1552 0.114 Uiso 1 1 calc R
C16 C 0.0558(4) 0.1611(3) -0.0568(3) 0.0707(13) Uani 1 1 d .
N3 N -0.0084(3) 0.1922(3) 0.1441(3) 0.0807(12) Uani 1 1 d .
C18 C 0.0029(4) 0.2769(4) 0.0779(4) 0.0899(16) Uani 1 1 d .
H18 H -0.0112 0.3472 0.1006 0.108 Uiso 1 1 calc R
C15 C 0.0435(4) 0.0747(4) 0.0112(4) 0.0902(16) Uani 1 1 d .
H15 H 0.0566 0.0034 -0.0094 0.108 Uiso 1 1 calc R
N4 N 0.1103(4) 0.1255(3) -0.2454(4) 0.1110(15) Uani 1 1 d .
C17 C 0.0344(5) 0.2640(4) -0.0224(4) 0.0804(13) Uani 1 1 d .
H17 H 0.0411 0.3246 -0.066 0.097 Uiso 1 1 calc R
C19 C 0.0872(5) 0.1410(4) -0.1626(4) 0.0815(14) 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
C1 C6 C5 121.2(4)
C1 C6 H6 119.4
C5 C6 H6 119.4
C12 N1 C8 117.1(4)
C10 C9 C8 118.2(4)
C10 C9 H9 120.9
C8 C9 H9 120.9
O2 C7 O1 121.8(4)
O2 C7 C1 123.8(4)
O1 C7 C1 114.4(4)
C7 O1 H3O 110(3)
O3 C2 C3 118.1(3)
O3 C2 C1 121.9(3)
C3 C2 C1 119.9(3)
C5 C4 C3 119.5(4)
C5 C4 H4 120.2
C3 C4 H4 120.2
C2 O3 H1O 109.5
C5 O4 H2O 113(3)
N2 C13 C10 177.0(6)
C12 C11 C10 117.2(4)
C12 C11 H11 121.4
C10 C11 H11 121.4
C6 C1 C2 118.5(4)
C6 C1 C7 122.1(3)
C2 C1 C7 119.4(4)
N1 C12 C11 124.3(4)
N1 C12 H12 117.9
C11 C12 H12 117.9
N1 C8 C9 122.6(4)
N1 C8 H8 118.7
C9 C8 H8 118.7
C9 C10 C11 120.7(4)
C9 C10 C13 120.7(4)
C11 C10 C13 118.6(4)
C2 C3 C4 120.5(4)
C2 C3 H3 119.8
C4 C3 H3 119.8
C6 C5 C4 120.3(4)
C6 C5 O4 118.1(4)
C4 C5 O4 121.6(4)
N3 C14 C15 123.6(4)
N3 C14 H14 118.2
C15 C14 H14 118.2
C17 C16 C15 117.5(4)
C17 C16 C19 122.4(4)
C15 C16 C19 120.0(4)
C14 N3 C18 117.3(4)
N3 C18 C17 122.9(4)
N3 C18 H18 118.6
C17 C18 H18 118.6
C16 C15 C14 119.4(4)
C16 C15 H15 120.3
C14 C15 H15 120.3
C16 C17 C18 119.3(4)
C16 C17 H17 120.4
C18 C17 H17 120.4
N4 C19 C16 179.2(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C1 1.374(5)
C6 C5 1.377(5)
C6 H6 0.93
N1 C12 1.334(5)
N1 C8 1.335(5)
C9 C10 1.361(5)
C9 C8 1.376(6)
C9 H9 0.93
C7 O2 1.222(4)
C7 O1 1.330(5)
C7 C1 1.477(5)
O1 H3O 0.89(5)
C2 O3 1.370(4)
C2 C3 1.379(5)
C2 C1 1.410(5)
C4 C5 1.377(5)
C4 C3 1.383(5)
C4 H4 0.93
O3 H1O 0.82
O4 C5 1.385(5)
O4 H2O 0.95(5)
C13 N2 1.163(5)
C13 C10 1.444(6)
C11 C12 1.362(6)
C11 C10 1.367(6)
C11 H11 0.93
C12 H12 0.93
C8 H8 0.93
C3 H3 0.93
C14 N3 1.300(6)
C14 C15 1.382(5)
C14 H14 0.93
C16 C17 1.369(6)
C16 C15 1.377(6)
C16 C19 1.458(7)
N3 C18 1.343(6)
C18 C17 1.381(7)
C18 H18 0.93
C15 H15 0.93
N4 C19 1.133(5)
C17 H17 0.93
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652488
2 PubChem 168345118
