#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:35:14 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301801 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/15/2021514.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021514
loop_
_publ_author_name
'Powers, Kyle A.'
'Geiger, David K.'
_publ_section_title
;
 Hydrogen bonding in two benzene-1,2-diaminium pyridine-2-carboxylate
 salts and a cocrystal of benzene-1,2-diamine and benzoic acid
;
_journal_coeditor_code           FN3292
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619002262
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C6 H8 N2, 2C7 H6 O2'
_chemical_formula_moiety         'C6 H8 N2, 2(C7 H6 O2)'
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38
_chemical_name_common            KAP02082017
_chemical_name_systematic
;
Benzene-1,2-diamine bis(benzoic acid)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.061(3)
_cell_length_b                   7.8464(10)
_cell_length_c                   11.6895(12)
_cell_measurement_reflns_used    4994
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      24.2332
_cell_measurement_theta_min      2.7849
_cell_volume                     1840.0(4)
_computing_cell_refinement
;
APEX2 (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30170
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'XOS X-beam microfocus source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.121
_refine_ls_extinction_coef       0.036(2)
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0426P)²+0.2144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                1337
_reflns_number_total             1638
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fn3292sup1.cif
_cod_data_source_block           3
_cod_depositor_comments
;

2019-10-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C6 H8 N2), C7 H6 O2'
_cod_original_formula_iupac      '0.5C6 H8 N2, C7 H6 O2'
_cod_original_formula_sum        'C10 H10 N O2'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     176.19
_cod_database_code               2021514
_cod_database_fobs_code          2021514
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.35377(4) 0.51824(13) 0.24544(7) 0.0577(3) Uani d 1
H H1C 0.3984(9) 0.489(2) 0.2143(15) 0.094(5) Uiso d 1
O O2 0.40648(4) 0.59582(12) 0.40443(7) 0.0566(3) Uani d 1
N N1 0.46617(5) 0.40589(14) 0.14608(9) 0.0445(3) Uani d 1
H H1A 0.4497(7) 0.3912(16) 0.0737(13) 0.061(4) Uiso d 1
H H1B 0.5014(8) 0.4803(19) 0.1440(12) 0.060(4) Uiso d 1
C C1 0.16309(8) 0.6783(2) 0.48889(14) 0.0698(4) Uani d 1
H H1 0.1204 0.7037 0.5196 0.084 Uiso calc 1
C C2 0.21951(8) 0.71645(18) 0.55063(13) 0.0661(4) Uani d 1
H H2 0.2156 0.7662 0.6244 0.079 Uiso calc 1
C C3 0.28164(7) 0.68275(16) 0.50592(11) 0.0537(4) Uani d 1
H H3 0.3205 0.7097 0.5488 0.064 Uiso calc 1
C C4 0.28756(6) 0.60956(14) 0.39861(10) 0.0421(3) Uani d 1
C C5 0.35476(6) 0.57469(14) 0.35138(10) 0.0425(3) Uani d 1
C C6 0.16825(7) 0.6037(2) 0.38286(14) 0.0668(4) Uani d 1
H H6 0.1292 0.5757 0.341 0.08 Uiso calc 1
C C7 0.23038(6) 0.56947(16) 0.33734(12) 0.0534(3) Uani d 1
H H7 0.234 0.5184 0.2639 0.064 Uiso calc 1
C C8 0.48442(7) -0.05934(19) 0.19776(14) 0.0703(4) Uani d 1
H H8 0.4736 -0.1642 0.1616 0.084 Uiso calc 1
C C9 0.46876(6) 0.09306(17) 0.14506(11) 0.0544(4) Uani d 1
H H9 0.4472 0.0922 0.0727 0.065 Uiso calc 1
C C10 0.48419(5) 0.24690(15) 0.19649(10) 0.0403(3) Uani d 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 O1 H1C . . 114.1(10)
C10 N1 H1A . . 111.3(8)
C10 N1 H1B . . 111.9(9)
H1A N1 H1B . . 109.5(12)
C6 C1 C2 . . 120.25(13)
C6 C1 H1 . . 119.9
C2 C1 H1 . . 119.9
C1 C2 C3 . . 120.26(13)
C1 C2 H2 . . 119.9
C3 C2 H2 . . 119.9
C2 C3 C4 . . 120.07(13)
C2 C3 H3 . . 120.0
C4 C3 H3 . . 120.0
C3 C4 C7 . . 119.36(11)
C3 C4 C5 . . 119.48(11)
C7 C4 C5 . . 121.16(11)
O2 C5 O1 . . 122.49(11)
O2 C5 C4 . . 123.99(11)
O1 C5 C4 . . 113.52(10)
C1 C6 C7 . . 119.87(14)
C1 C6 H6 . . 120.1
C7 C6 H6 . . 120.1
C6 C7 C4 . . 120.17(13)
C6 C7 H7 . . 119.9
C4 C7 H7 . . 119.9
C8 C8 C9 3_655 . 120.04(8)
C8 C8 H8 3_655 . 120.0
C9 C8 H8 . . 120.0
C8 C9 C10 . . 120.69(12)
C8 C9 H9 . . 119.7
C10 C9 H9 . . 119.7
C9 C10 C10 . 3_655 119.26(7)
C9 C10 N1 . . 121.79(11)
C10 C10 N1 3_655 . 118.89(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C5 . 1.3153(14)
O1 H1C . 0.994(19)
O2 C5 . 1.2201(14)
N1 C10 . 1.4262(15)
N1 H1A . 0.916(15)
N1 H1B . 0.916(16)
C1 C6 . 1.375(2)
C1 C2 . 1.375(2)
C1 H1 . 0.95
C2 C3 . 1.3771(19)
C2 H2 . 0.95
C3 C4 . 1.3848(17)
C3 H3 . 0.95
C4 C7 . 1.3885(17)
C4 C5 . 1.4822(16)
C6 C7 . 1.3816(19)
C6 H6 . 0.95
C7 H7 . 0.95
C8 C8 3_655 1.372(3)
C8 C9 . 1.3814(19)
C8 H8 . 0.95
C9 C10 . 1.3836(17)
C9 H9 . 0.95
C10 C10 3_655 1.403(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1C N1 . 0.994(19) 1.706(19) 2.6852(13) 167.8(16) yes
N1 H1A O2 7_565 0.916(15) 2.163(16) 3.0681(14) 169.8(12) yes
N1 H1B O2 3_655 0.916(16) 2.136(16) 3.0160(14) 160.8(12) yes
C6 H6 <i>Cg</i>(bda) 8_566 0.95 2.81 3.7163(16) 161 y
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . 1.1(2)
C1 C2 C3 C4 . . -0.3(2)
C2 C3 C4 C7 . . -0.53(19)
C2 C3 C4 C5 . . 179.74(11)
C3 C4 C5 O2 . . 5.18(18)
C7 C4 C5 O2 . . -174.54(11)
C3 C4 C5 O1 . . -174.73(11)
C7 C4 C5 O1 . . 5.54(16)
C2 C1 C6 C7 . . -1.1(2)
C1 C6 C7 C4 . . 0.3(2)
C3 C4 C7 C6 . . 0.52(19)
C5 C4 C7 C6 . . -179.75(11)
C8 C8 C9 C10 3_655 . 0.0(3)
C8 C9 C10 C10 . 3_655 -0.3(2)
C8 C9 C10 N1 . . -177.43(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71381436
