#------------------------------------------------------------------------------
#$Date: 2024-03-20 04:57:46 +0200 (Wed, 20 Mar 2024) $
#$Revision: 290543 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312429.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_2312429
loop_
_publ_author_name
'Balasubramanian, Hemalatha'
'Mariappan, Petchi Raman'
'Poomani, Kumaradhas'
_publ_section_title
;
 Crystal structure, intermolecular interactions, charge-density
 distribution and ADME properties of the acridinium 4-nitrobenzoate and
 2-amino-3-methylpyridinium 4-nitrobenzoate salts: a combined experimental
 and theoretical study.
;
_journal_coeditor_code           EF3054
_journal_issue                   4
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624002250
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C13 H10 N1 +, C7 H4 N1 O4 -'
_chemical_formula_moiety         'C13 H10 N1 +, C7 H4 N1 O4 -'
_chemical_formula_sum            'C20 H14 N2 O4'
_chemical_formula_weight         346.33
_chemical_name_systematic
;
Acridin-10-ium 4-nitrobenzoate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.3800(10)
_cell_angle_beta                 95.0050(10)
_cell_angle_gamma                93.7800(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6186(2)
_cell_length_b                   9.4985(2)
_cell_length_c                   11.9173(3)
_cell_measurement_reflns_used    4100
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.23
_cell_volume                     824.78(3)
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
Mercury (Macrae et al.,  2020) and
PLATON (Spek, 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Three-circle Fixed Chi diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22030
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.972
_diffrn_reflns_theta_min         2.233
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2006)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.758
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.192
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0912P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.158
_refine_ls_wR_factor_ref         0.1659
_reflns_number_gt                3338
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef3054sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        824.77(3)
_cod_database_code               2312429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.54165(15) 0.56623(12) 0.21295(11) 0.0668(3) Uani d 1 . .
N N2 0.37822(14) 0.77264(11) 0.34098(9) 0.0459(3) Uani d 1 . .
H H2A 0.423114 0.701267 0.295365 0.055 Uiso calc 1 . .
O O4 0.78800(19) 0.70691(15) 0.29466(15) 0.1020(6) Uani d 1 . .
C C20 0.38824(15) 0.90582(13) 0.32079(11) 0.0424(3) Uani d 1 . .
N N1 1.1229(2) 0.16723(18) -0.03261(13) 0.0718(4) Uani d 1 . .
O O2 1.2828(2) 0.1862(2) -0.00949(14) 0.1014(5) Uani d 1 . .
C C8 0.29822(16) 0.75062(14) 0.43226(11) 0.0455(3) Uani d 1 . .
C C13 0.22403(15) 0.86719(15) 0.51010(11) 0.0457(3) Uani d 1 . .
C C15 0.31603(15) 1.02724(13) 0.39465(11) 0.0432(3) Uani d 1 . .
C C4 0.81614(18) 0.48421(13) 0.15489(11) 0.0469(3) Uani d 1 . .
C C19 0.47551(19) 0.92710(16) 0.22490(12) 0.0521(3) Uani d 1 . .
C C1 1.01560(19) 0.27927(16) 0.03319(12) 0.0531(3) Uani d 1 . .
C C3 0.73362(19) 0.35560(15) 0.07913(13) 0.0526(3) Uani d 1 . .
C C5 1.0001(2) 0.50946(16) 0.16718(13) 0.0535(3) Uani d 1 . .
C C7 0.7123(2) 0.59752(15) 0.22730(13) 0.0582(4) Uani d 1 . .
C C14 0.23589(16) 1.00515(15) 0.48980(11) 0.0465(3) Uani d 1 . .
C C6 1.10170(19) 0.40661(17) 0.10640(13) 0.0553(3) Uani d 1 . .
O O1 1.0455(2) 0.06176(19) -0.10658(16) 0.1091(6) Uani d 1 . .
C C2 0.8346(2) 0.25109(17) 0.01754(13) 0.0577(4) Uani d 1 . .
C C12 0.14156(19) 0.8376(2) 0.60534(13) 0.0587(4) Uani d 1 . .
C C16 0.33119(19) 1.16520(15) 0.36816(14) 0.0555(3) Uani d 1 . .
C C18 0.4863(2) 1.06030(18) 0.20314(14) 0.0599(4) Uani d 1 . .
C C9 0.2888(2) 0.60884(17) 0.45210(15) 0.0594(4) Uani d 1 . .
C C11 0.1319(2) 0.7003(2) 0.62023(16) 0.0690(5) Uani d 1 . .
C C17 0.4128(2) 1.18062(17) 0.27497(15) 0.0616(4) Uani d 1 . .
C C10 0.2070(2) 0.5862(2) 0.54345(17) 0.0688(4) Uani d 1 . .
H H12 0.100(2) 0.9205(18) 0.6581(14) 0.053(4) Uiso d 1 . .
H H16 0.285(2) 1.245(2) 0.4182(16) 0.067(5) Uiso d 1 . .
H H6 1.226(3) 0.426(2) 0.1128(17) 0.080(6) Uiso d 1 . .
H H3 0.607(3) 0.337(2) 0.0702(16) 0.071(5) Uiso d 1 . .
H H14 0.192(2) 1.0847(18) 0.5403(14) 0.055(4) Uiso d 1 . .
H H19 0.527(2) 0.8461(19) 0.1765(15) 0.062(4) Uiso d 1 . .
H H2 0.776(3) 0.167(2) -0.0305(18) 0.075(5) Uiso d 1 . .
H H17 0.423(3) 1.272(2) 0.2600(18) 0.088(6) Uiso d 1 . .
H H5 1.054(2) 0.595(2) 0.2226(17) 0.070(5) Uiso d 1 . .
H H18 0.549(3) 1.074(2) 0.1385(18) 0.078(5) Uiso d 1 . .
H H9 0.343(2) 0.534(2) 0.3967(15) 0.063(5) Uiso d 1 . .
H H11 0.073(3) 0.681(2) 0.683(2) 0.093(7) Uiso d 1 . .
H H10 0.202(3) 0.488(3) 0.5555(19) 0.092(6) Uiso 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 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C20 N2 C8 . . 120.39(11) ?
C20 N2 H2A . . 119.8 ?
C8 N2 H2A . . 119.8 ?
N2 C20 C19 . . 119.44(11) ?
N2 C20 C15 . . 121.55(11) ?
C19 C20 C15 . . 119.01(12) ?
O2 N1 O1 . . 124.04(16) ?
O2 N1 C1 . . 117.87(16) ?
O1 N1 C1 . . 118.09(16) ?
N2 C8 C9 . . 119.56(12) ?
N2 C8 C13 . . 121.10(12) ?
C9 C8 C13 . . 119.34(13) ?
C14 C13 C12 . . 122.91(13) ?
C14 C13 C8 . . 118.46(12) ?
C12 C13 C8 . . 118.63(13) ?
C14 C15 C16 . . 123.29(12) ?
C14 C15 C20 . . 118.08(12) ?
C16 C15 C20 . . 118.62(12) ?
C3 C4 C5 . . 119.82(12) ?
C3 C4 C7 . . 121.61(12) ?
C5 C4 C7 . . 118.55(12) ?
C18 C19 C20 . . 120.18(13) ?
C18 C19 H19 . . 120.7(11) ?
C20 C19 H19 . . 119.1(11) ?
C2 C1 C6 . . 123.12(13) ?
C2 C1 N1 . . 118.36(14) ?
C6 C1 N1 . . 118.52(14) ?
C4 C3 C2 . . 119.86(13) ?
C4 C3 H3 . . 120.5(11) ?
C2 C3 H3 . . 119.6(11) ?
C6 C5 C4 . . 120.83(13) ?
C6 C5 H5 . . 120.4(12) ?
C4 C5 H5 . . 118.6(11) ?
O4 C7 O3 . . 124.39(14) ?
O4 C7 C4 . . 120.17(15) ?
O3 C7 C4 . . 115.43(12) ?
C15 C14 C13 . . 120.40(11) ?
C15 C14 H14 . . 118.8(10) ?
C13 C14 H14 . . 120.8(10) ?
C1 C6 C5 . . 117.81(13) ?
C1 C6 H6 . . 121.7(12) ?
C5 C6 H6 . . 120.4(12) ?
C1 C2 C3 . . 118.54(13) ?
C1 C2 H2 . . 124.2(13) ?
C3 C2 H2 . . 117.3(13) ?
C11 C12 C13 . . 120.44(15) ?
C11 C12 H12 . . 123.8(10) ?
C13 C12 H12 . . 115.7(10) ?
C17 C16 C15 . . 120.66(13) ?
C17 C16 H16 . . 121.3(11) ?
C15 C16 H16 . . 118.0(11) ?
C19 C18 C17 . . 121.12(14) ?
C19 C18 H18 . . 119.4(12) ?
C17 C18 H18 . . 119.4(12) ?
C10 C9 C8 . . 119.63(15) ?
C10 C9 H9 . . 124.9(11) ?
C8 C9 H9 . . 115.5(11) ?
C12 C11 C10 . . 120.49(15) ?
C12 C11 H11 . . 119.4(14) ?
C10 C11 H11 . . 120.1(14) ?
C16 C17 C18 . . 120.40(14) ?
C16 C17 H17 . . 119.1(13) ?
C18 C17 H17 . . 120.5(13) ?
C9 C10 C11 . . 121.46(16) ?
C9 C10 H10 . . 118.3(13) ?
C11 C10 H10 . . 120.2(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 C7 . 1.3002(19) ?
N2 C20 . 1.3475(17) ?
N2 C8 . 1.3484(17) ?
N2 H2A . 0.86 ?
O4 C7 . 1.2061(18) ?
C20 C19 . 1.4235(19) ?
C20 C15 . 1.4273(17) ?
N1 O2 . 1.216(2) ?
N1 O1 . 1.221(2) ?
N1 C1 . 1.4833(19) ?
C8 C9 . 1.426(2) ?
C8 C13 . 1.4267(18) ?
C13 C14 . 1.3929(19) ?
C13 C12 . 1.426(2) ?
C15 C14 . 1.3903(19) ?
C15 C16 . 1.4269(19) ?
C4 C3 . 1.3847(18) ?
C4 C5 . 1.3944(19) ?
C4 C7 . 1.5060(19) ?
C19 C18 . 1.356(2) ?
C19 H19 . 0.962(18) ?
C1 C2 . 1.374(2) ?
C1 C6 . 1.375(2) ?
C3 C2 . 1.389(2) ?
C3 H3 . 0.96(2) ?
C5 C6 . 1.379(2) ?
C5 H5 . 0.943(19) ?
C14 H14 . 0.934(17) ?
C6 H6 . 0.95(2) ?
C2 H2 . 0.91(2) ?
C12 C11 . 1.360(3) ?
C12 H12 . 0.959(17) ?
C16 C17 . 1.355(2) ?
C16 H16 . 0.941(19) ?
C18 C17 . 1.415(2) ?
C18 H18 . 0.98(2) ?
C9 C10 . 1.358(2) ?
C9 H9 . 0.973(18) ?
C11 C10 . 1.410(3) ?
C11 H11 . 0.96(2) ?
C17 H17 . 0.93(2) ?
C10 H10 . 0.98(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
N2 H2A O3 , 0.8600 1.7500 2.6055(16) 172.00 yes
C14 H14 O4 2_676 0.934(17) 2.378(17) 3.245(2) 154.5(13) yes
C19 H19 O2 2_765 0.960(17) 2.529(16) 3.280(2) 135.2(14) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N2 C20 C19 . . . . 179.11(11) ?
C8 N2 C20 C15 . . . . 0.24(18) ?
C20 N2 C8 C9 . . . . 179.94(11) ?
C20 N2 C8 C13 . . . . -0.61(18) ?
N2 C8 C13 C14 . . . . 0.02(18) ?
C9 C8 C13 C14 . . . . 179.46(11) ?
N2 C8 C13 C12 . . . . -179.80(11) ?
C9 C8 C13 C12 . . . . -0.35(19) ?
N2 C20 C15 C14 . . . . 0.71(18) ?
C19 C20 C15 C14 . . . . -178.16(11) ?
N2 C20 C15 C16 . . . . -179.96(11) ?
C19 C20 C15 C16 . . . . 1.16(18) ?
N2 C20 C19 C18 . . . . 179.78(12) ?
C15 C20 C19 C18 . . . . -1.3(2) ?
O2 N1 C1 C2 . . . . -172.69(15) ?
O1 N1 C1 C2 . . . . 7.3(2) ?
O2 N1 C1 C6 . . . . 7.7(2) ?
O1 N1 C1 C6 . . . . -172.34(16) ?
C5 C4 C3 C2 . . . . 1.3(2) ?
C7 C4 C3 C2 . . . . -177.31(13) ?
C3 C4 C5 C6 . . . . -1.2(2) ?
C7 C4 C5 C6 . . . . 177.41(12) ?
C3 C4 C7 O4 . . . . 178.20(17) ?
C5 C4 C7 O4 . . . . -0.4(2) ?
C3 C4 C7 O3 . . . . -0.4(2) ?
C5 C4 C7 O3 . . . . -179.01(12) ?
C16 C15 C14 C13 . . . . 179.41(11) ?
C20 C15 C14 C13 . . . . -1.30(18) ?
C12 C13 C14 C15 . . . . -179.23(11) ?
C8 C13 C14 C15 . . . . 0.96(18) ?
C2 C1 C6 C5 . . . . 0.5(2) ?
N1 C1 C6 C5 . . . . -179.82(12) ?
C4 C5 C6 C1 . . . . 0.3(2) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
N1 C1 C2 C3 . . . . 179.89(13) ?
C4 C3 C2 C1 . . . . -0.5(2) ?
C14 C13 C12 C11 . . . . 179.22(12) ?
C8 C13 C12 C11 . . . . -1.0(2) ?
C14 C15 C16 C17 . . . . 179.15(13) ?
C20 C15 C16 C17 . . . . -0.1(2) ?
C20 C19 C18 C17 . . . . 0.4(2) ?
N2 C8 C9 C10 . . . . -179.46(13) ?
C13 C8 C9 C10 . . . . 1.1(2) ?
C13 C12 C11 C10 . . . . 1.6(2) ?
C15 C16 C17 C18 . . . . -0.8(2) ?
C19 C18 C17 C16 . . . . 0.6(2) ?
C8 C9 C10 C11 . . . . -0.5(3) ?
C12 C11 C10 C9 . . . . -0.8(3) ?

_cod_database_fobs_code 2312429
