#------------------------------------------------------------------------------
#$Date: 2022-01-07 00:35:07 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022497.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_2022497
loop_
_publ_author_name
'Suganya, Suresh'
'Saravanan, Kandasamy'
'Jaganathan, Ramakrishnan'
'Kumaradhas, Poomani'
_publ_section_title
;
 Salt formation, hydrogen-bonding patterns and supramolecular
 architectures of acridine with salicylic and hippuric acid molecules
;
_journal_coeditor_code           EF3021
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              790
_journal_page_last               799
_journal_paper_doi               10.1107/S2053229621011189
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C13 H10 N +, C7 H6 N O3 -'
_chemical_formula_moiety         'C13 H10 N +, C7 H6 N O3 -'
_chemical_formula_sum            'C20 H16 N2 O3'
_chemical_formula_weight         332.35
_chemical_name_common
;
Acridin-1-ium 4-aminosalicylate
;
_chemical_name_systematic
;
Acridin-1-ium 4-amino-2-hydroxybenzoate
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1209(5)
_cell_length_b                   12.1988(12)
_cell_length_c                   20.1202(18)
_cell_measurement_reflns_used    20496
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.62
_cell_volume                     1747.8(3)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
PLATON (Spek, 2020),
OLEX2 (Dolomanov et al., 2009) and
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO'
_diffrn_measurement_method       'omega and phi 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  0.023
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20496
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.883
_exptl_crystal_size_mid          0.504
_exptl_crystal_size_min          0.225
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
;
Flack (1983)
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0369
_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)+(0.0765P)²+0.0658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                3934
_reflns_number_total             4274
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ef3021sup1.cif
_cod_data_source_block           I
_cod_database_code               2022497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.62266(13) 0.74164(9) 0.29886(6) 0.0559(3) Uani d . 1 1 . .
O O2 0.51812(15) 0.57511(9) 0.36654(5) 0.0552(3) Uani d . 1 1 . .
O O1 0.22130(16) 0.51923(8) 0.36038(6) 0.0590(3) Uani d . 1 1 . .
N N2 0.1561(2) 0.96426(10) 0.19765(8) 0.0610(3) Uani d . 1 1 . .
N N1 0.26192(16) 0.37488(9) 0.45353(5) 0.0442(2) Uani d . 1 1 . .
C C15 0.29836(16) 0.69110(9) 0.31332(6) 0.0367(2) Uani d . 1 1 . .
C C14 0.34981(18) 0.58939(10) 0.34906(6) 0.0421(3) Uani d . 1 1 . .
C C18 0.20294(17) 0.87705(9) 0.23705(6) 0.0417(2) Uani d . 1 1 . .
C C16 0.43767(16) 0.76183(10) 0.28820(6) 0.0395(3) Uani d . 1 1 . .
C C20 0.11121(16) 0.71904(10) 0.30111(6) 0.0414(3) Uani d . 1 1 . .
C C19 0.06189(17) 0.80983(11) 0.26471(7) 0.0437(3) Uani d . 1 1 . .
C C17 0.39049(17) 0.85247(10) 0.25015(7) 0.0443(3) Uani d . 1 1 . .
C C7 0.2536(2) 0.22836(11) 0.55772(6) 0.0501(3) Uani d . 1 1 . .
C C6 0.2548(2) 0.18865(10) 0.49289(6) 0.0460(3) Uani d . 1 1 . .
C C1 0.25990(17) 0.26626(10) 0.43989(6) 0.0425(3) Uani d . 1 1 . .
C C2 0.2618(2) 0.22936(13) 0.37333(7) 0.0540(3) Uani d . 1 1 . .
C C8 0.25627(19) 0.34026(11) 0.57105(6) 0.0465(3) Uani d . 1 1 . .
C C9 0.26015(19) 0.41456(11) 0.51636(6) 0.0451(3) Uani d . 1 1 . .
C C5 0.2516(3) 0.07505(12) 0.47674(9) 0.0615(4) Uani d . 1 1 . .
C C13 0.2540(2) 0.38421(15) 0.63666(7) 0.0605(4) Uani d . 1 1 . .
C C3 0.2577(3) 0.12005(15) 0.36041(8) 0.0660(4) Uani d . 1 1 . .
C C4 0.2527(3) 0.04228(15) 0.41247(10) 0.0700(4) Uani d . 1 1 . .
C C10 0.2624(3) 0.52876(13) 0.52776(8) 0.0624(4) Uani d . 1 1 . .
C C12 0.2562(3) 0.49381(18) 0.64618(9) 0.0726(5) Uani d . 1 1 . .
C C11 0.2594(3) 0.56670(16) 0.59123(10) 0.0753(5) Uani d . 1 1 . .
H H10 0.258(3) 0.5774(17) 0.4891(10) 0.075(6) Uiso d . 1 1 . .
H H20 0.016(3) 0.6723(16) 0.3195(9) 0.065(5) Uiso d . 1 1 . .
H H2B 0.245(3) 0.9962(16) 0.1749(9) 0.063(5) Uiso d . 1 1 . .
H H1A 0.256(3) 0.4329(15) 0.4155(9) 0.065(5) Uiso d . 1 1 . .
H H13 0.247(3) 0.3311(17) 0.6764(11) 0.075(6) Uiso d . 1 1 . .
H H5 0.247(3) 0.0230(17) 0.5138(9) 0.074(6) Uiso d . 1 1 . .
H H2 0.260(3) 0.2835(14) 0.3402(9) 0.058(5) Uiso d . 1 1 . .
H H7 0.246(3) 0.1771(16) 0.5939(10) 0.067(5) Uiso d . 1 1 . .
H H3 0.260(3) 0.0930(16) 0.3120(10) 0.071(6) Uiso d . 1 1 . .
H H12 0.252(4) 0.526(2) 0.6973(11) 0.094(7) Uiso d . 1 1 . .
H H2A 0.021(3) 0.9765(18) 0.1899(10) 0.073(6) Uiso d . 1 1 . .
H H19 -0.073(2) 0.8282(13) 0.2554(8) 0.049(4) Uiso d . 1 1 . .
H H17 0.493(3) 0.8951(15) 0.2308(9) 0.059(5) Uiso d . 1 1 . .
H H16 0.615(3) 0.685(2) 0.3293(11) 0.074(6) Uiso d . 1 1 . .
H H4 0.257(4) -0.0347(19) 0.3991(10) 0.087(7) Uiso d . 1 1 . .
H H11 0.272(3) 0.648(2) 0.5982(12) 0.096(7) Uiso d . 1 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
C16 O3 H16 . . 100.5(14) ?
C18 N2 H2B . . 118.4(14) ?
C18 N2 H2A . . 116.6(12) ?
H2B N2 H2A . . 123.7(18) ?
C1 N1 C9 . . 122.64(10) ?
C1 N1 H1A . . 121.1(10) ?
C9 N1 H1A . . 116.2(10) ?
C20 C15 C16 . . 117.34(11) ?
C20 C15 C14 . . 121.73(10) ?
C16 C15 C14 . . 120.90(11) ?
O2 C14 O1 . . 122.70(12) ?
O2 C14 C15 . . 119.11(11) ?
O1 C14 C15 . . 118.19(11) ?
N2 C18 C17 . . 120.69(12) ?
N2 C18 C19 . . 120.46(12) ?
C17 C18 C19 . . 118.84(12) ?
O3 C16 C17 . . 117.86(11) ?
O3 C16 C15 . . 121.04(11) ?
C17 C16 C15 . . 121.07(11) ?
C19 C20 C15 . . 122.30(11) ?
C19 C20 H20 . . 120.2(12) ?
C15 C20 H20 . . 117.5(12) ?
C20 C19 C18 . . 119.80(11) ?
C20 C19 H19 . . 121.6(10) ?
C18 C19 H19 . . 118.5(9) ?
C16 C17 C18 . . 120.55(11) ?
C16 C17 H17 . . 117.5(11) ?
C18 C17 H17 . . 121.8(11) ?
C8 C7 C6 . . 121.48(11) ?
C8 C7 H7 . . 119.6(12) ?
C6 C7 H7 . . 118.9(12) ?
C7 C6 C5 . . 123.56(13) ?
C7 C6 C1 . . 118.02(12) ?
C5 C6 C1 . . 118.41(13) ?
N1 C1 C2 . . 120.26(11) ?
N1 C1 C6 . . 119.91(11) ?
C2 C1 C6 . . 119.83(12) ?
C3 C2 C1 . . 119.59(14) ?
C3 C2 H2 . . 123.6(11) ?
C1 C2 H2 . . 116.7(11) ?
C7 C8 C13 . . 123.20(13) ?
C7 C8 C9 . . 118.38(12) ?
C13 C8 C9 . . 118.42(13) ?
N1 C9 C10 . . 120.29(13) ?
N1 C9 C8 . . 119.57(12) ?
C10 C9 C8 . . 120.14(13) ?
C4 C5 C6 . . 120.37(15) ?
C4 C5 H5 . . 122.4(12) ?
C6 C5 H5 . . 117.2(12) ?
C12 C13 C8 . . 120.24(15) ?
C12 C13 H13 . . 120.9(12) ?
C8 C13 H13 . . 118.9(12) ?
C2 C3 C4 . . 121.15(14) ?
C2 C3 H3 . . 119.7(11) ?
C4 C3 H3 . . 119.1(11) ?
C5 C4 C3 . . 120.65(15) ?
C5 C4 H4 . . 123.2(12) ?
C3 C4 H4 . . 116.1(12) ?
C11 C10 C9 . . 119.25(16) ?
C11 C10 H10 . . 122.7(12) ?
C9 C10 H10 . . 118.0(12) ?
C13 C12 C11 . . 120.67(15) ?
C13 C12 H12 . . 118.9(13) ?
C11 C12 H12 . . 120.5(13) ?
C10 C11 C12 . . 121.28(17) ?
C10 C11 H11 . . 117.7(14) ?
C12 C11 H11 . . 120.7(14) ?
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 C16 . 1.3571(14) ?
O3 H16 . 0.93(2) ?
O2 C14 . 1.2611(17) ?
O1 C14 . 1.2735(16) ?
N2 C18 . 1.3679(17) ?
N2 H2B . 0.87(2) ?
N2 H2A . 0.98(2) ?
N1 C1 . 1.3532(17) ?
N1 C9 . 1.3538(16) ?
N1 H1A . 1.043(19) ?
C15 C20 . 1.3973(16) ?
C15 C16 . 1.4086(16) ?
C15 C14 . 1.4802(16) ?
C18 C17 . 1.3939(17) ?
C18 C19 . 1.4110(18) ?
C16 C17 . 1.3862(18) ?
C20 C19 . 1.3736(19) ?
C20 H20 . 0.96(2) ?
C19 H19 . 1.004(17) ?
C17 H17 . 0.98(2) ?
C7 C8 . 1.3912(19) ?
C7 C6 . 1.3915(19) ?
C7 H7 . 0.96(2) ?
C6 C5 . 1.424(2) ?
C6 C1 . 1.4265(17) ?
C1 C2 . 1.4130(18) ?
C2 C3 . 1.359(2) ?
C2 H2 . 0.939(19) ?
C8 C13 . 1.4250(19) ?
C8 C9 . 1.4258(17) ?
C9 C10 . 1.412(2) ?
C5 C4 . 1.354(3) ?
C5 H5 . 0.98(2) ?
C13 C12 . 1.351(3) ?
C13 H13 . 1.03(2) ?
C3 C4 . 1.414(3) ?
C3 H3 . 1.03(2) ?
C4 H4 . 0.98(2) ?
C10 C11 . 1.359(2) ?
C10 H10 . 0.98(2) ?
C12 C11 . 1.419(3) ?
C12 H12 . 1.10(2) ?
C11 H11 . 1.01(3) ?
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
C20 C15 C14 O2 . . . . -170.66(12) ?
C16 C15 C14 O2 . . . . 11.57(17) ?
C20 C15 C14 O1 . . . . 9.93(17) ?
C16 C15 C14 O1 . . . . -167.84(12) ?
C20 C15 C16 O3 . . . . 178.85(11) ?
C14 C15 C16 O3 . . . . -3.29(18) ?
C20 C15 C16 C17 . . . . -3.07(17) ?
C14 C15 C16 C17 . . . . 174.79(11) ?
C16 C15 C20 C19 . . . . 1.69(18) ?
C14 C15 C20 C19 . . . . -176.15(12) ?
C15 C20 C19 C18 . . . . 1.4(2) ?
N2 C18 C19 C20 . . . . 176.39(13) ?
C17 C18 C19 C20 . . . . -3.10(19) ?
O3 C16 C17 C18 . . . . 179.53(12) ?
C15 C16 C17 C18 . . . . 1.39(19) ?
N2 C18 C17 C16 . . . . -177.76(13) ?
C19 C18 C17 C16 . . . . 1.74(19) ?
C8 C7 C6 C5 . . . . -179.80(15) ?
C8 C7 C6 C1 . . . . 0.3(2) ?
C9 N1 C1 C2 . . . . 179.98(12) ?
C9 N1 C1 C6 . . . . 0.31(19) ?
C7 C6 C1 N1 . . . . -0.51(19) ?
C5 C6 C1 N1 . . . . 179.60(14) ?
C7 C6 C1 C2 . . . . 179.82(13) ?
C5 C6 C1 C2 . . . . -0.07(19) ?
N1 C1 C2 C3 . . . . -179.29(14) ?
C6 C1 C2 C3 . . . . 0.4(2) ?
C6 C7 C8 C13 . . . . 179.61(14) ?
C6 C7 C8 C9 . . . . 0.1(2) ?
C1 N1 C9 C10 . . . . -179.98(14) ?
C1 N1 C9 C8 . . . . 0.09(19) ?
C7 C8 C9 N1 . . . . -0.3(2) ?
C13 C8 C9 N1 . . . . -179.84(13) ?
C7 C8 C9 C10 . . . . 179.79(15) ?
C13 C8 C9 C10 . . . . 0.2(2) ?
C7 C6 C5 C4 . . . . 179.90(17) ?
C1 C6 C5 C4 . . . . -0.2(3) ?
C7 C8 C13 C12 . . . . -179.78(17) ?
C9 C8 C13 C12 . . . . -0.2(2) ?
C1 C2 C3 C4 . . . . -0.4(3) ?
C6 C5 C4 C3 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
N1 C9 C10 C11 . . . . 179.63(17) ?
C8 C9 C10 C11 . . . . -0.5(3) ?
C8 C13 C12 C11 . . . . 0.5(3) ?
C9 C10 C11 C12 . . . . 0.7(3) ?
C13 C12 C11 C10 . . . . -0.7(3) ?

_cod_database_fobs_code 2022497
