#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:07:37 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312663.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_2312663
loop_
_publ_author_name
'Mohana, Marimuthu'
'Gomathi, Sundaramoorthy'
'Thomas Muthiah, Packianathan'
'Butcher, Ray J.'
_publ_section_title
;
 Hydrogen-bonding interactions in the salts 2,4,6-triaminopyrimidin-1-ium
 sorbate dihydrate, 2,4,6-triaminopyrimidin-1-ium N-phenylantharanilate
 and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate.
;
_journal_coeditor_code           OV3175
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              728
_journal_page_last               733
_journal_paper_doi               10.1107/S2053229624008763
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C4 H8 N5 +, C13 H10 N O2 -'
_chemical_formula_moiety         'C4 H8 N5 +, C13 H10 N O2 -'
_chemical_formula_sum            'C17 H18 N6 O2'
_chemical_formula_weight         338.37
_chemical_name_common
;
2,4,6-Triaminopyrimidin-1-ium N-phenylanthranilate
;
_chemical_name_systematic
;
2,4,6-Triaminopyrimidin-1-ium 2-(phenylamino)benzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.538(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1498(8)
_cell_length_b                   12.1582(6)
_cell_length_c                   20.6224(10)
_cell_measurement_reflns_used    10186
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      41.3
_cell_measurement_theta_min      2.8
_cell_volume                     3160.7(3)
_computing_cell_refinement
;
APEX2 (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
APEX2 (Bruker, 2014)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020), Mercury (Macrae et al., 2020) and
POVRay (Cason,
2004)
;
_computing_publication_material
;
PLATON (Spek, 2020) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10681
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         2.787
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0464
_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)+(0.0304P)²+4.6822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                2961
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3175sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2312662--2312664.cif.'
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2312663
_cod_database_fobs_code          2312663
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.44515(14) 0.08042(14) 0.57748(8) 0.0147(3) Uani d 1 . .
C C4 0.56213(14) -0.01785(15) 0.66021(8) 0.0156(4) Uani d 1 . .
C C5 0.53192(14) 0.03861(15) 0.71079(9) 0.0173(4) Uani d 1 . .
H H5 0.562344 0.021014 0.757159 0.021 Uiso calc 1 . .
C C6 0.45743(14) 0.11981(15) 0.69180(8) 0.0163(4) Uani d 1 . .
C C7 0.11145(15) 0.38971(15) 0.61560(8) 0.0169(4) Uani d 1 . .
C C8 0.10240(15) 0.50179(16) 0.63149(9) 0.0187(4) Uani d 1 . .
C C9 0.00131(16) 0.54770(17) 0.61769(10) 0.0225(4) Uani d 1 . .
H H9 -0.005746 0.623091 0.627718 0.027 Uiso calc 1 . .
C C10 -0.08837(16) 0.48641(18) 0.58992(10) 0.0246(4) Uani d 1 . .
H H10 -0.156275 0.519929 0.580516 0.030 Uiso calc 1 . .
C C11 -0.08022(16) 0.37615(17) 0.57559(9) 0.0222(4) Uani d 1 . .
H H11 -0.142167 0.333138 0.557633 0.027 Uiso calc 1 . .
C C12 0.01937(15) 0.32935(16) 0.58777(9) 0.0188(4) Uani d 1 . .
H H12 0.025067 0.254113 0.576869 0.023 Uiso calc 1 . .
C C13 0.21578(15) 0.33173(15) 0.63012(8) 0.0162(4) Uani d 1 . .
C C14 0.20922(15) 0.67250(15) 0.64340(9) 0.0190(4) Uani d 1 . .
C C15 0.29173(16) 0.73194(17) 0.68571(10) 0.0230(4) Uani d 1 . .
H H15 0.330860 0.701414 0.727833 0.028 Uiso calc 1 . .
C C16 0.31760(17) 0.83506(18) 0.66724(11) 0.0288(5) Uani d 1 . .
H H16 0.374651 0.874727 0.696546 0.035 Uiso calc 1 . .
C C17 0.26074(18) 0.88100(18) 0.60617(12) 0.0297(5) Uani d 1 . .
H H17 0.278670 0.951779 0.593266 0.036 Uiso calc 1 . .
C C18 0.17806(17) 0.82275(17) 0.56452(11) 0.0256(4) Uani d 1 . .
H H18 0.138912 0.853751 0.522547 0.031 Uiso calc 1 . .
C C19 0.15096(16) 0.71978(16) 0.58272(10) 0.0219(4) Uani d 1 . .
H H19 0.092593 0.681309 0.553823 0.026 Uiso calc 1 . .
N N1 0.41434(12) 0.14070(12) 0.62432(7) 0.0151(3) Uani d 1 . .
H H1 0.3575(17) 0.1892(18) 0.6107(10) 0.015(5) Uiso d 1 . .
N N2 0.39847(13) 0.10306(14) 0.51263(7) 0.0186(3) Uani d 1 . .
H H2A 0.3639(18) 0.1636(16) 0.5000(12) 0.028(6) Uiso d 1 . .
H H2B 0.4217(18) 0.0658(19) 0.4828(11) 0.030(6) Uiso d 1 . .
N N3 0.51713(12) 0.00197(13) 0.59342(7) 0.0154(3) Uani d 1 . .
N N4 0.63787(13) -0.09401(13) 0.67571(8) 0.0190(3) Uani d 1 . .
H H4A 0.6723(17) -0.1055(19) 0.7177(8) 0.025(6) Uiso d 1 . .
H H4B 0.6599(18) -0.1235(19) 0.6437(10) 0.027(6) Uiso d 1 . .
N N5 0.42206(15) 0.18231(15) 0.73387(8) 0.0237(4) Uani d 1 . .
H H5A 0.448(2) 0.172(2) 0.7764(13) 0.033(7) Uiso d 1 . .
H H5B 0.380(2) 0.241(3) 0.7177(14) 0.054(9) Uiso d 1 . .
N N6 0.19120(14) 0.56471(14) 0.66224(8) 0.0211(3) Uani d 1 . .
H H6 0.253(2) 0.525(2) 0.6822(13) 0.036(7) Uiso d 1 . .
O O1 0.29001(11) 0.36318(11) 0.67998(6) 0.0195(3) Uani d 1 . .
O O2 0.22436(10) 0.25204(11) 0.59280(6) 0.0183(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
_geom_angle_publ_flag
N3 C2 N2 . . 119.53(16) ?
N3 C2 N1 . . 123.36(15) ?
N2 C2 N1 . . 117.10(16) ?
N4 C4 N3 . . 116.60(15) ?
N4 C4 C5 . . 120.99(16) ?
N3 C4 C5 . . 122.41(16) ?
C6 C5 C4 . . 118.27(16) ?
C6 C5 H5 . . 120.9 ?
C4 C5 H5 . . 120.9 ?
N5 C6 C5 . . 125.42(17) ?
N5 C6 N1 . . 115.84(17) ?
C5 C6 N1 . . 118.74(16) ?
C12 C7 C8 . . 118.86(17) ?
C12 C7 C13 . . 118.35(16) ?
C8 C7 C13 . . 122.74(17) ?
N6 C8 C9 . . 120.09(17) ?
N6 C8 C7 . . 121.41(17) ?
C9 C8 C7 . . 118.46(18) ?
C10 C9 C8 . . 121.53(18) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C9 C10 C11 . . 120.32(18) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 119.11(18) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C11 C12 C7 . . 121.68(18) ?
C11 C12 H12 . . 119.2 ?
C7 C12 H12 . . 119.2 ?
O1 C13 O2 . . 123.23(17) ?
O1 C13 C7 . . 118.32(16) ?
O2 C13 C7 . . 118.43(16) ?
C15 C14 C19 . . 118.85(18) ?
C15 C14 N6 . . 118.37(18) ?
C19 C14 N6 . . 122.71(17) ?
C16 C15 C14 . . 120.7(2) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C15 C16 C17 . . 120.3(2) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C18 C17 C16 . . 119.1(2) ?
C18 C17 H17 . . 120.5 ?
C16 C17 H17 . . 120.5 ?
C17 C18 C19 . . 121.1(2) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C18 C19 C14 . . 119.97(19) ?
C18 C19 H19 . . 120.0 ?
C14 C19 H19 . . 120.0 ?
C2 N1 C6 . . 120.02(15) ?
C2 N1 H1 . . 120.2(12) ?
C6 N1 H1 . . 119.3(12) ?
C2 N2 H2A . . 122.0(16) ?
C2 N2 H2B . . 116.1(16) ?
H2A N2 H2B . . 119(2) ?
C2 N3 C4 . . 117.15(15) ?
C4 N4 H4A . . 119.7(16) ?
C4 N4 H4B . . 119.5(16) ?
H4A N4 H4B . . 120(2) ?
C6 N5 H5A . . 118.3(17) ?
C6 N5 H5B . . 120.0(18) ?
H5A N5 H5B . . 121(2) ?
C8 N6 C14 . . 124.96(17) ?
C8 N6 H6 . . 115.0(16) ?
C14 N6 H6 . . 114.6(16) ?
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
C2 N3 . 1.318(2) ?
C2 N2 . 1.332(2) ?
C2 N1 . 1.363(2) ?
C4 N4 . 1.331(2) ?
C4 N3 . 1.357(2) ?
C4 C5 . 1.397(2) ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.9500 ?
C6 N5 . 1.333(2) ?
C6 N1 . 1.369(2) ?
C7 C12 . 1.392(3) ?
C7 C8 . 1.414(3) ?
C7 C13 . 1.495(3) ?
C8 N6 . 1.389(2) ?
C8 C9 . 1.394(3) ?
C9 C10 . 1.375(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.384(3) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 O1 . 1.259(2) ?
C13 O2 . 1.262(2) ?
C14 C15 . 1.386(3) ?
C14 C19 . 1.392(3) ?
C14 N6 . 1.406(2) ?
C15 C16 . 1.381(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.386(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.375(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.383(3) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
N1 H1 . 0.93(2) ?
N2 H2A . 0.865(16) ?
N2 H2B . 0.884(16) ?
N4 H4A . 0.866(16) ?
N4 H4B . 0.869(16) ?
N5 H5A . 0.85(3) ?
N5 H5B . 0.91(3) ?
N6 H6 . 0.93(3) ?
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
N1 H1 O2 . 0.93(2) 1.85(2) 2.752(2) 162.9(19) yes
N2 H2A O2 2_556 0.865(16) 2.21(2) 2.936(2) 141(2) yes
N2 H2B N3 5_656 0.884(16) 2.126(17) 3.004(2) 172(2) yes
N4 H4A O1 4_546 0.866(16) 2.062(17) 2.902(2) 163(2) yes
N4 H4B O2 6_655 0.869(16) 2.185(18) 3.003(2) 157(2) yes
N5 H5B O1 . 0.91(3) 1.92(3) 2.826(2) 178(3) yes
N6 H6 O1 . 0.93(3) 2.03(3) 2.749(2) 133(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N4 C4 C5 C6 . . . . 176.75(17) ?
N3 C4 C5 C6 . . . . -2.8(3) ?
C4 C5 C6 N5 . . . . -178.57(18) ?
C4 C5 C6 N1 . . . . 1.3(3) ?
C12 C7 C8 N6 . . . . 176.95(16) ?
C13 C7 C8 N6 . . . . -0.4(3) ?
C12 C7 C8 C9 . . . . -0.9(2) ?
C13 C7 C8 C9 . . . . -178.22(16) ?
N6 C8 C9 C10 . . . . -177.23(17) ?
C7 C8 C9 C10 . . . . 0.6(3) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
C9 C10 C11 C12 . . . . -1.9(3) ?
C10 C11 C12 C7 . . . . 1.6(3) ?
C8 C7 C12 C11 . . . . -0.2(3) ?
C13 C7 C12 C11 . . . . 177.23(16) ?
C12 C7 C13 O1 . . . . -147.40(17) ?
C8 C7 C13 O1 . . . . 29.9(2) ?
C12 C7 C13 O2 . . . . 31.0(2) ?
C8 C7 C13 O2 . . . . -151.69(17) ?
C19 C14 C15 C16 . . . . -1.7(3) ?
N6 C14 C15 C16 . . . . 175.33(18) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C15 C16 C17 C18 . . . . 0.3(3) ?
C16 C17 C18 C19 . . . . 0.1(3) ?
C17 C18 C19 C14 . . . . -1.4(3) ?
C15 C14 C19 C18 . . . . 2.2(3) ?
N6 C14 C19 C18 . . . . -174.73(17) ?
N3 C2 N1 C6 . . . . -1.1(3) ?
N2 C2 N1 C6 . . . . 178.48(16) ?
N5 C6 N1 C2 . . . . -179.57(17) ?
C5 C6 N1 C2 . . . . 0.6(3) ?
N2 C2 N3 C4 . . . . -179.92(16) ?
N1 C2 N3 C4 . . . . -0.4(3) ?
N4 C4 N3 C2 . . . . -177.25(16) ?
C5 C4 N3 C2 . . . . 2.3(3) ?
C9 C8 N6 C14 . . . . -46.2(3) ?
C7 C8 N6 C14 . . . . 136.03(19) ?
C15 C14 N6 C8 . . . . 168.98(17) ?
C19 C14 N6 C8 . . . . -14.1(3) ?
