#------------------------------------------------------------------------------
#$Date: 2023-12-04 11:36:27 +0200 (Mon, 04 Dec 2023) $
#$Revision: 287972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107709.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_8107709
loop_
_publ_author_name
'Smith, Mark G.'
_publ_section_title
;
 The crystal structure of the salt:
 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate,
 C14H10N3O3·C8H5O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1227
_journal_page_last               1228
_journal_paper_doi               10.1515/ncrs-2023-0417
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C14 H10 N3 O3, C8 H5 O4'
_chemical_formula_sum            'C22 H15 N3 O7'
_chemical_formula_weight         433.37
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_cell_angle_alpha                110.933(2)
_cell_angle_beta                 101.603(2)
_cell_angle_gamma                91.295(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1312(3)
_cell_length_b                   10.5732(4)
_cell_length_c                   12.0961(4)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.21
_cell_measurement_wavelength     0.71073
_cell_volume                     946.37(6)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012) [4]'
_computing_publication_material
'WinGX publication routines (Farrugia, 2012) [5]'
_computing_structure_refinement  'SHELXL-2015/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT-2015/2 (Sheldrick, 2015) [2]'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14217
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.85
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0593P)²+0.2185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0
_reflns_number_gt                2937
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0417_suppl_001.cif
_cod_data_source_block           shelx
_cod_database_code               8107709
_shelx_shelxl_version_number     2015/3
_publcif_funding_html
;
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5449(2) 0.16425(18) 0.46116(15) 0.0262(4) Uani 1 1 d . . . . .
C2 C 0.5811(2) 0.24257(18) 0.59650(15) 0.0242(4) Uani 1 1 d . . . . .
C3 C 0.5145(2) 0.36283(19) 0.65133(16) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.437264 0.399733 0.603863 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5618(3) 0.4278(2) 0.77525(16) 0.0322(5) Uani 1 1 d . . . . .
H4 H 0.514936 0.509225 0.813737 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7394(3) 0.26249(19) 0.79175(16) 0.0306(5) Uani 1 1 d . . . . .
H5 H 0.818914 0.229485 0.841257 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6934(2) 0.19145(18) 0.66885(15) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.738003 0.10787 0.633413 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5057(3) 0.2320(2) 0.21158(17) 0.0360(5) Uani 1 1 d . . . . .
C8 C 0.4229(3) 0.1658(2) 0.08092(17) 0.0389(5) Uani 1 1 d . . . . .
C9 C 0.4670(3) 0.1833(2) -0.01673(19) 0.0482(6) Uani 1 1 d . . . . .
H9 H 0.558923 0.2469 -0.005792 0.058 Uiso 1 1 calc R U . . .
C10 C 0.3744(4) 0.1060(3) -0.1309(2) 0.0541(7) Uani 1 1 d . . . . .
H10 H 0.402815 0.115695 -0.20008 0.065 Uiso 1 1 calc R U . . .
C11 C 0.2406(4) 0.0145(3) -0.1459(2) 0.0607(8) Uani 1 1 d . . . . .
H11 H 0.177295 -0.0371 -0.225503 0.073 Uiso 1 1 calc R U . . .
C12 C 0.1953(3) -0.0042(3) -0.0451(2) 0.0536(7) Uani 1 1 d . . . . .
H12 H 0.104157 -0.067956 -0.054859 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2909(3) 0.0752(2) 0.06797(17) 0.0410(6) Uani 1 1 d . . . . .
C14 C 0.2794(3) 0.0800(2) 0.19166(19) 0.0374(5) Uani 1 1 d . . . . .
N1 N 0.4383(2) 0.21912(18) 0.39431(13) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.6728(2) 0.37790(16) 0.84223(14) 0.0301(4) Uani 1 1 d . . . . .
N3 N 0.4174(2) 0.16765(17) 0.26974(13) 0.0348(4) Uani 1 1 d . . . . .
O1 O 0.61114(18) 0.06184(13) 0.41769(11) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.6216(2) 0.31991(16) 0.26162(14) 0.0491(4) Uani 1 1 d . . . . .
O3 O 0.1775(2) 0.02278(16) 0.22208(15) 0.0500(4) Uani 1 1 d . . . . .
H2 H 0.706(3) 0.425(2) 0.926(2) 0.06 Uiso 1 1 d . U . . .
C15 C 0.1524(3) 0.4397(2) 0.34621(17) 0.0317(5) Uani 1 1 d . . . . .
C16 C 0.0454(2) 0.55637(18) 0.35745(15) 0.0256(4) Uani 1 1 d . . . . .
C17 C -0.0721(2) 0.57976(18) 0.26479(15) 0.0259(4) Uani 1 1 d . . . . .
C18 C -0.1433(3) 0.70270(19) 0.29432(17) 0.0331(5) Uani 1 1 d . . . . .
H18A H -0.2186 0.720511 0.23181 0.04 Uiso 1 1 calc R U . . .
C19 C -0.1093(3) 0.7999(2) 0.41054(18) 0.0376(5) Uani 1 1 d . . . . .
H19A H -0.1594 0.883056 0.427275 0.045 Uiso 1 1 calc R U . . .
C20 C -0.0016(3) 0.7741(2) 0.50174(17) 0.0369(5) Uani 1 1 d . . . . .
H20A H 0.0197 0.838038 0.582865 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0750(3) 0.6555(2) 0.47516(16) 0.0313(5) Uani 1 1 d . . . . .
H21A H 0.15074 0.640106 0.53886 0.038 Uiso 1 1 calc R U . . .
C22 C -0.1345(3) 0.4846(2) 0.13344(16) 0.0321(5) Uani 1 1 d . . . . .
O4 O 0.25504(19) 0.44073(15) 0.43538(12) 0.0408(4) Uani 1 1 d . . . . .
O5 O 0.1388(2) 0.34188(16) 0.24257(14) 0.0564(5) Uani 1 1 d . . . . .
O6 O -0.0670(2) 0.37799(15) 0.08790(13) 0.0526(5) Uani 1 1 d . . . . .
O7 O -0.2573(2) 0.51703(15) 0.07231(12) 0.0453(4) Uani 1 1 d . . . . .
H5A H 0.056(4) 0.354(3) 0.174(2) 0.068 Uiso 1 1 d . U . . .
H1 H 0.383(3) 0.295(2) 0.421(2) 0.049(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
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N1 123.62(16) . .
O1 C1 C2 121.57(16) . .
N1 C1 C2 114.79(16) . .
C3 C2 C6 118.87(16) . .
C3 C2 C1 124.30(15) . .
C6 C2 C1 116.79(16) . .
C4 C3 C2 119.06(16) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
N2 C4 C3 120.76(18) . .
N2 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
N2 C5 C6 120.33(17) . .
N2 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C5 C6 C2 119.52(17) . .
C5 C6 H6 120.2 . .
C2 C6 H6 120.2 . .
O2 C7 N3 125.45(18) . .
O2 C7 C8 130.3(2) . .
N3 C7 C8 104.25(19) . .
C13 C8 C9 122.3(2) . .
C13 C8 C7 109.14(19) . .
C9 C8 C7 128.6(2) . .
C8 C9 C10 118.1(3) . .
C8 C9 H9 121 . .
C10 C9 H9 121 . .
C9 C10 C11 120.6(2) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C10 C11 C12 121.4(2) . .
C10 C11 H11 119.3 . .
C12 C11 H11 119.3 . .
C13 C12 C11 116.3(3) . .
C13 C12 H12 121.8 . .
C11 C12 H12 121.8 . .
C8 C13 C12 121.3(2) . .
C8 C13 C14 108.49(18) . .
C12 C13 C14 130.2(3) . .
O3 C14 N3 125.0(2) . .
O3 C14 C13 130.4(2) . .
N3 C14 C13 104.6(2) . .
C1 N1 N3 119.17(16) . .
C1 N1 H1 128.0(14) . .
N3 N1 H1 112.5(14) . .
C4 N2 C5 121.42(16) . .
C4 N2 H2 119.2(15) . .
C5 N2 H2 119.4(15) . .
N1 N3 C14 123.26(19) . .
N1 N3 C7 120.96(17) . .
C14 N3 C7 113.06(17) . .
O4 C15 O5 120.41(19) . .
O4 C15 C16 119.27(17) . .
O5 C15 C16 120.29(17) . .
C21 C16 C17 117.69(17) . .
C21 C16 C15 113.84(16) . .
C17 C16 C15 128.40(16) . .
C18 C17 C16 118.22(16) . .
C18 C17 C22 114.07(16) . .
C16 C17 C22 127.70(16) . .
C19 C18 C17 122.84(18) . .
C19 C18 H18A 118.6 . .
C17 C18 H18A 118.6 . .
C20 C19 C18 118.84(19) . .
C20 C19 H19A 120.6 . .
C18 C19 H19A 120.6 . .
C21 C20 C19 119.87(18) . .
C21 C20 H20A 120.1 . .
C19 C20 H20A 120.1 . .
C20 C21 C16 122.42(17) . .
C20 C21 H21A 118.8 . .
C16 C21 H21A 118.8 . .
O7 C22 O6 121.32(17) . .
O7 C22 C17 116.69(17) . .
O6 C22 C17 121.99(17) . .
C15 O5 H5A 113.8(15) . .
C22 O6 H5A 111.9(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.214(2) .
C1 N1 1.348(2) .
C1 C2 1.510(2) .
C2 C3 1.387(3) .
C2 C6 1.389(2) .
C3 C4 1.374(2) .
C3 H3 0.95 .
C4 N2 1.335(2) .
C4 H4 0.95 .
C5 N2 1.336(2) .
C5 C6 1.371(2) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 O2 1.203(3) .
C7 N3 1.413(3) .
C7 C8 1.484(3) .
C8 C13 1.369(3) .
C8 C9 1.371(3) .
C9 C10 1.375(3) .
C9 H9 0.95 .
C10 C11 1.378(4) .
C10 H10 0.95 .
C11 C12 1.419(4) .
C11 H11 0.95 .
C12 C13 1.379(3) .
C12 H12 0.95 .
C13 C14 1.501(3) .
C14 O3 1.203(3) .
C14 N3 1.382(3) .
N1 N3 1.379(2) .
N1 H1 0.92(2) .
N2 H2 0.93(2) .
C15 O4 1.221(2) .
C15 O5 1.291(2) .
C15 C16 1.507(3) .
C16 C21 1.403(2) .
C16 C17 1.417(2) .
C17 C18 1.392(3) .
C17 C22 1.518(2) .
C18 C19 1.381(3) .
C18 H18A 0.95 .
C19 C20 1.377(3) .
C19 H19A 0.95 .
C20 C21 1.375(3) .
C20 H20A 0.95 .
C21 H21A 0.95 .
C22 O7 1.249(2) .
C22 O6 1.258(2) .
O5 H5A 1.01(3) .
O6 H5A 1.39(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O4 0.95 2.45 3.369(2) 164 . yes
C4 H4 O2 0.95 2.49 3.209(3) 132.8 2_666 yes
C5 H5 O3 0.95 2.5 3.059(2) 117.6 2_656 yes
C6 H6 O3 0.95 2.59 3.108(2) 114.4 2_656 yes
N2 H2 O6 0.93(2) 2.61(2) 3.283(2) 129.8(19) 1_656 yes
N2 H2 O7 0.93(2) 1.65(3) 2.575(2) 173(2) 1_656 yes
O5 H5A O6 1.01(3) 1.39(3) 2.393(2) 175(3) . yes
N1 H1 O4 0.92(2) 1.86(2) 2.753(2) 166(2) . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 177.48(19) . . . .
N1 C1 C2 C3 -0.8(3) . . . .
O1 C1 C2 C6 -0.3(3) . . . .
N1 C1 C2 C6 -178.57(19) . . . .
C6 C2 C3 C4 0.2(3) . . . .
C1 C2 C3 C4 -177.53(19) . . . .
C2 C3 C4 N2 1.3(3) . . . .
N2 C5 C6 C2 2.1(3) . . . .
C3 C2 C6 C5 -1.8(3) . . . .
C1 C2 C6 C5 176.04(18) . . . .
O2 C7 C8 C13 -177.3(2) . . . .
N3 C7 C8 C13 2.9(2) . . . .
O2 C7 C8 C9 4.9(4) . . . .
N3 C7 C8 C9 -174.9(2) . . . .
C13 C8 C9 C10 -0.2(3) . . . .
C7 C8 C9 C10 177.40(19) . . . .
C8 C9 C10 C11 0.4(3) . . . .
C9 C10 C11 C12 -0.8(3) . . . .
C10 C11 C12 C13 0.8(3) . . . .
C9 C8 C13 C12 0.3(3) . . . .
C7 C8 C13 C12 -177.72(18) . . . .
C9 C8 C13 C14 179.03(19) . . . .
C7 C8 C13 C14 1.1(2) . . . .
C11 C12 C13 C8 -0.6(3) . . . .
C11 C12 C13 C14 -179.1(2) . . . .
C8 C13 C14 O3 175.7(2) . . . .
C12 C13 C14 O3 -5.7(4) . . . .
C8 C13 C14 N3 -4.7(2) . . . .
C12 C13 C14 N3 173.9(2) . . . .
O1 C1 N1 N3 -8.2(3) . . . .
C2 C1 N1 N3 170.07(17) . . . .
C3 C4 N2 C5 -1.1(3) . . . .
C6 C5 N2 C4 -0.6(3) . . . .
C1 N1 N3 C14 101.8(2) . . . .
C1 N1 N3 C7 -98.2(2) . . . .
O3 C14 N3 N1 -12.1(3) . . . .
C13 C14 N3 N1 168.27(16) . . . .
O3 C14 N3 C7 -173.5(2) . . . .
C13 C14 N3 C7 6.9(2) . . . .
O2 C7 N3 N1 12.0(3) . . . .
C8 C7 N3 N1 -168.15(16) . . . .
O2 C7 N3 C14 173.9(2) . . . .
C8 C7 N3 C14 -6.3(2) . . . .
O4 C15 C16 C21 -1.5(3) . . . .
O5 C15 C16 C21 -179.5(2) . . . .
O4 C15 C16 C17 175.5(2) . . . .
O5 C15 C16 C17 -2.6(3) . . . .
C21 C16 C17 C18 3.7(3) . . . .
C15 C16 C17 C18 -173.1(2) . . . .
C21 C16 C17 C22 -175.36(19) . . . .
C15 C16 C17 C22 7.8(3) . . . .
C16 C17 C18 C19 -2.6(3) . . . .
C22 C17 C18 C19 176.6(2) . . . .
C17 C18 C19 C20 -0.6(4) . . . .
C18 C19 C20 C21 2.6(3) . . . .
C19 C20 C21 C16 -1.3(3) . . . .
C17 C16 C21 C20 -1.9(3) . . . .
C15 C16 C21 C20 175.4(2) . . . .
C18 C17 C22 O7 -9.8(3) . . . .
C16 C17 C22 O7 169.3(2) . . . .
C18 C17 C22 O6 170.3(2) . . . .
C16 C17 C22 O6 -10.6(3) . . . .
