#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:07:37 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312664.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_2312664
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 +, C7 H7 O3 S -'
_chemical_formula_moiety         'C4 H8 N5 +, C7 H7 O3 S -'
_chemical_formula_sum            'C11 H15 N5 O3 S'
_chemical_formula_weight         297.34
_chemical_name_common
;
2,4,6-Triaminopyrimidin-1-ium p-toluenesulfonate
;
_chemical_name_systematic
;
2,4,6-Triaminopyrimidin-1-ium 4-methylbenzene-1-sulfonate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                92.7270(10)
_cell_angle_beta                 104.992(2)
_cell_angle_gamma                99.1940(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8382(3)
_cell_length_b                   8.3657(4)
_cell_length_c                   12.5848(6)
_cell_measurement_reflns_used    3958
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.9
_cell_volume                     683.50(6)
_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_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.945
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11436
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.579
_diffrn_reflns_theta_min         2.862
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.554
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0403
_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)+(0.0273P)²+0.6477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                3406
_reflns_number_total             3956
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3175sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
'Adding full bibliography for 2312662--2312664.cif.'
_cod_database_code               2312664
_cod_database_fobs_code          2312664
_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   0.940
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_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
C C2 1.0429(2) 0.83514(16) 0.87921(12) 0.0145(3) Uani d 1 . .
C C4 1.2182(2) 1.09792(16) 0.91876(11) 0.0138(2) Uani d 1 . .
C C5 1.0367(2) 1.16001(16) 0.87605(12) 0.0151(3) Uani d 1 . .
H H5 1.039298 1.273782 0.874923 0.018 Uiso calc 1 . .
C C6 0.8560(2) 1.05093(17) 0.83608(12) 0.0146(3) Uani d 1 . .
C C7 0.2863(2) 0.40082(17) 0.65470(12) 0.0163(3) Uani d 1 . .
C C8 0.3609(2) 0.3423(2) 0.57086(15) 0.0276(4) Uani d 1 . .
H H8 0.504174 0.364419 0.576722 0.033 Uiso calc 1 . .
C C9 0.2250(3) 0.2508(2) 0.47803(15) 0.0291(4) Uani d 1 . .
H H9 0.276541 0.211659 0.420465 0.035 Uiso calc 1 . .
C C10 0.0145(2) 0.21581(19) 0.46832(13) 0.0202(3) Uani d 1 . .
C C11 -0.0578(2) 0.2802(2) 0.55142(14) 0.0230(3) Uani d 1 . .
H H11 -0.201413 0.260999 0.544531 0.028 Uiso calc 1 . .
C C12 0.0758(2) 0.3725(2) 0.64476(13) 0.0213(3) Uani d 1 . .
H H12 0.023763 0.415572 0.700923 0.026 Uiso calc 1 . .
C C13 -0.1331(3) 0.1118(2) 0.36963(14) 0.0261(3) Uani d 1 . .
H H13A -0.247173 0.049978 0.392481 0.039 Uiso calc 1 . .
H H13B -0.060662 0.036331 0.339597 0.039 Uiso calc 1 . .
H H13C -0.186955 0.181648 0.312840 0.039 Uiso calc 1 . .
N N1 0.86210(18) 0.88856(14) 0.83890(10) 0.0148(2) Uani d 1 . .
H H1 0.746(4) 0.816(3) 0.8115(19) 0.035(6) Uiso d 1 . .
N N2 1.0342(2) 0.67449(15) 0.87713(12) 0.0200(3) Uani d 1 . .
H H2A 1.150(3) 0.638(3) 0.8915(18) 0.027(5) Uiso d 1 . .
H H2B 0.914(3) 0.610(3) 0.8494(18) 0.029(5) Uiso d 1 . .
N N3 1.22126(17) 0.93536(14) 0.91941(10) 0.0145(2) Uani d 1 . .
N N4 1.39760(19) 1.19630(15) 0.96345(11) 0.0180(2) Uani d 1 . .
H H4A 1.507(3) 1.158(3) 0.9955(18) 0.030(6) Uiso d 1 . .
H H4B 1.408(3) 1.298(3) 0.9605(18) 0.025(5) Uiso d 1 . .
N N5 0.6701(2) 1.08955(16) 0.79206(12) 0.0204(3) Uani d 1 . .
H H5A 0.557(3) 1.016(3) 0.7800(18) 0.030(6) Uiso d 1 . .
H H5B 0.659(3) 1.188(3) 0.7960(17) 0.022(5) Uiso d 1 . .
O O1 0.50204(16) 0.68142(13) 0.74340(10) 0.0217(2) Uani d 1 . .
O O2 0.35876(16) 0.50318(12) 0.86189(9) 0.0178(2) Uani d 1 . .
O O3 0.64561(15) 0.44096(13) 0.79621(10) 0.0203(2) Uani d 1 . .
S S1 0.46003(5) 0.51457(4) 0.77291(3) 0.01580(9) 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'
S S 0.1246 0.1234 '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 . . 120.33(13) ?
N3 C2 N1 . . 122.80(12) ?
N2 C2 N1 . . 116.87(12) ?
N4 C4 N3 . . 115.92(12) ?
N4 C4 C5 . . 121.38(13) ?
N3 C4 C5 . . 122.68(12) ?
C6 C5 C4 . . 117.95(12) ?
C6 C5 H5 . . 121.0 ?
C4 C5 H5 . . 121.0 ?
N5 C6 N1 . . 116.06(12) ?
N5 C6 C5 . . 125.53(13) ?
N1 C6 C5 . . 118.40(12) ?
C8 C7 C12 . . 120.21(14) ?
C8 C7 S1 . . 119.42(11) ?
C12 C7 S1 . . 120.37(12) ?
C7 C8 C9 . . 119.71(15) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C8 C9 C10 . . 121.00(16) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C11 C10 C9 . . 118.31(14) ?
C11 C10 C13 . . 120.40(14) ?
C9 C10 C13 . . 121.29(15) ?
C10 C11 C12 . . 121.48(14) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C7 C12 C11 . . 119.21(14) ?
C7 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C2 N1 C6 . . 121.16(12) ?
C2 N1 H1 . . 119.4(15) ?
C6 N1 H1 . . 119.4(15) ?
C2 N2 H2A . . 117.6(14) ?
C2 N2 H2B . . 118.8(14) ?
H2A N2 H2B . . 123(2) ?
C2 N3 C4 . . 116.99(12) ?
C4 N4 H4A . . 121.2(15) ?
C4 N4 H4B . . 120.3(14) ?
H4A N4 H4B . . 119(2) ?
C6 N5 H5A . . 120.8(15) ?
C6 N5 H5B . . 118.2(14) ?
H5A N5 H5B . . 118(2) ?
O2 S1 O1 . . 112.39(7) ?
O2 S1 O3 . . 112.56(7) ?
O1 S1 O3 . . 111.55(6) ?
O2 S1 C7 . . 106.99(7) ?
O1 S1 C7 . . 106.39(7) ?
O3 S1 C7 . . 106.46(7) ?
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 . 1.3266(17) ?
C2 N2 . 1.3344(17) ?
C2 N1 . 1.3637(17) ?
C4 N4 . 1.3325(17) ?
C4 N3 . 1.3638(17) ?
C4 C5 . 1.4091(18) ?
C5 C6 . 1.3739(19) ?
C5 H5 . 0.9500 ?
C6 N5 . 1.3460(18) ?
C6 N1 . 1.3675(17) ?
C7 C8 . 1.387(2) ?
C7 C12 . 1.392(2) ?
C7 S1 . 1.7664(15) ?
C8 C9 . 1.393(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.394(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.388(2) ?
C10 C13 . 1.512(2) ?
C11 C12 . 1.394(2) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
N1 H1 . 0.90(2) ?
N2 H2A . 0.87(2) ?
N2 H2B . 0.89(2) ?
N4 H4A . 0.87(2) ?
N4 H4B . 0.85(2) ?
N5 H5A . 0.88(2) ?
N5 H5B . 0.84(2) ?
O1 S1 . 1.4646(11) ?
O2 S1 . 1.4604(12) ?
O3 S1 . 1.4664(11) ?
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 S1 . 0.90(2) 2.87(2) 3.7230(12) 159.8(19) yes
N1 H1 O1 . 0.90(2) 1.83(2) 2.7234(16) 174(2) yes
N2 H2A O2 1_655 0.87(2) 2.05(2) 2.8685(16) 156(2) yes
N2 H2B S1 . 0.89(2) 2.96(2) 3.7966(13) 157.7(18) yes
N2 H2B O3 . 0.89(2) 2.06(2) 2.9437(17) 174(2) yes
N4 H4A N3 2_877 0.87(2) 2.17(2) 3.0435(17) 178(2) yes
N4 H4B O2 1_665 0.85(2) 2.18(2) 2.9410(17) 148.9(19) yes
N5 H5B O3 1_565 0.84(2) 2.13(2) 2.9698(17) 175(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 . . . . -176.96(14) ?
N3 C4 C5 C6 . . . . 1.6(2) ?
C4 C5 C6 N5 . . . . -179.59(14) ?
C4 C5 C6 N1 . . . . -0.6(2) ?
C12 C7 C8 C9 . . . . -1.9(3) ?
S1 C7 C8 C9 . . . . 179.22(14) ?
C7 C8 C9 C10 . . . . -0.5(3) ?
C8 C9 C10 C11 . . . . 2.7(3) ?
C8 C9 C10 C13 . . . . -177.88(17) ?
C9 C10 C11 C12 . . . . -2.5(3) ?
C13 C10 C11 C12 . . . . 178.10(15) ?
C8 C7 C12 C11 . . . . 2.1(2) ?
S1 C7 C12 C11 . . . . -179.01(12) ?
C10 C11 C12 C7 . . . . 0.1(3) ?
N3 C2 N1 C6 . . . . 1.2(2) ?
N2 C2 N1 C6 . . . . -179.04(13) ?
N5 C6 N1 C2 . . . . 178.40(14) ?
C5 C6 N1 C2 . . . . -0.7(2) ?
N2 C2 N3 C4 . . . . 179.96(13) ?
N1 C2 N3 C4 . . . . -0.3(2) ?
N4 C4 N3 C2 . . . . 177.48(14) ?
C5 C4 N3 C2 . . . . -1.1(2) ?
C8 C7 S1 O2 . . . . -157.57(13) ?
C12 C7 S1 O2 . . . . 23.55(14) ?
C8 C7 S1 O1 . . . . 82.09(14) ?
C12 C7 S1 O1 . . . . -96.80(13) ?
C8 C7 S1 O3 . . . . -37.01(15) ?
C12 C7 S1 O3 . . . . 144.11(12) ?
