#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:07:37 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312662.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_2312662
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 +, C6 H7 O2 -, 2H2 O'
_chemical_formula_moiety         'C4 H8 N5 +, C6 H7 O2 -, 2(H2 O)'
_chemical_formula_sum            'C10 H19 N5 O4'
_chemical_formula_weight         273.30
_chemical_name_common
;
2,4,6-Triaminopyrimidin-1-ium sorbate dihydrate
;
_chemical_name_systematic
;
2,4,6-Triaminopyrimidin-1-ium 2,4-hexadienoate dihydrate
;
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                105.438(2)
_cell_angle_beta                 109.180(2)
_cell_angle_gamma                94.887(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2507(4)
_cell_length_b                   8.5870(4)
_cell_length_c                   10.6398(5)
_cell_measurement_reflns_used    3922
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.5
_cell_volume                     673.83(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 0.992
_diffrn_measured_fraction_theta_max 0.947
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11015
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         2.506
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0485
_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)+(0.0560P)²+0.3374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                3350
_reflns_number_total             3920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3175sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2312662--2312664.cif.'
_cod_database_code               2312662
_cod_database_fobs_code          2312662
_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   0.974
_shelx_estimated_absorpt_t_max   0.992
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 0.21036(14) 0.52917(14) 0.67628(12) 0.0125(2) Uani d 1 . .
C C4 -0.06518(14) 0.39295(14) 0.63045(12) 0.0125(2) Uani d 1 . .
C C5 -0.11729(14) 0.54083(14) 0.68159(13) 0.0134(2) Uani d 1 . .
H H5 -0.232072 0.541824 0.682225 0.016 Uiso calc 1 . .
C C6 0.00428(15) 0.68470(14) 0.73091(13) 0.0132(2) Uani d 1 . .
C C7 0.55092(15) 0.96261(14) 0.80555(12) 0.0131(2) Uani d 1 . .
C C8 0.66259(15) 1.12423(14) 0.83778(13) 0.0155(2) Uani d 1 . .
H H8 0.749630 1.127380 0.797690 0.019 Uiso calc 1 . .
C C9 0.64693(15) 1.26541(14) 0.92026(13) 0.0148(2) Uani d 1 . .
H H9 0.562729 1.261439 0.962998 0.018 Uiso calc 1 . .
C C10 0.75145(15) 1.42448(14) 0.94814(13) 0.0155(2) Uani d 1 . .
H H10 0.834099 1.429008 0.904022 0.019 Uiso calc 1 . .
C C11 0.73742(15) 1.56481(14) 1.03264(13) 0.0155(2) Uani d 1 . .
H H11 0.657594 1.558288 1.079028 0.019 Uiso calc 1 . .
C C12 0.83806(16) 1.73131(14) 1.05957(14) 0.0176(2) Uani d 1 . .
H H12A 0.910513 1.721961 1.002072 0.026 Uiso calc 1 . .
H H12B 0.913077 1.776338 1.158838 0.026 Uiso calc 1 . .
H H12C 0.756500 1.804669 1.035437 0.026 Uiso calc 1 . .
N N1 0.16783(12) 0.67700(12) 0.72768(11) 0.0126(2) Uani d 1 . .
H H1 0.257(3) 0.776(3) 0.763(2) 0.039(5) Uiso d 1 . .
N N2 0.37270(13) 0.53244(13) 0.67802(12) 0.0158(2) Uani d 1 . .
H H2A 0.397(3) 0.444(2) 0.636(2) 0.028(5) Uiso d 1 . .
H H2B 0.447(2) 0.629(2) 0.708(2) 0.024(4) Uiso d 1 . .
N N3 0.09825(12) 0.38690(12) 0.62823(11) 0.0130(2) Uani d 1 . .
N N4 -0.17461(14) 0.24794(13) 0.58301(12) 0.0163(2) Uani d 1 . .
H H4A -0.144(3) 0.160(2) 0.540(2) 0.028(5) Uiso d 1 . .
H H4B -0.283(3) 0.247(2) 0.575(2) 0.027(5) Uiso d 1 . .
N N5 -0.02680(14) 0.83504(13) 0.78272(13) 0.0184(2) Uani d 1 . .
H H5A 0.057(3) 0.924(3) 0.810(2) 0.037(5) Uiso d 1 . .
H H5B -0.128(3) 0.839(2) 0.7827(19) 0.023(4) Uiso d 1 . .
O O1 0.40374(11) 0.95944(10) 0.81822(10) 0.01632(19) Uani d 1 . .
O O2 0.61058(11) 0.83513(11) 0.76303(10) 0.01683(19) Uani d 1 . .
O O1W 0.21817(12) 0.08333(11) 0.60438(11) 0.0188(2) Uani d 1 . .
H H1WA 0.273(3) 0.072(3) 0.686(3) 0.041(6) Uiso d 1 . .
H H1WB 0.180(3) 0.170(3) 0.617(2) 0.035(5) Uiso d 1 . .
O O2W 0.45831(12) 0.23431(12) 0.52425(11) 0.0195(2) Uani d 1 . .
H H2WA 0.424(3) 0.206(3) 0.434(3) 0.049(6) Uiso d 1 . .
H H2WB 0.383(3) 0.171(3) 0.545(3) 0.050(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 0.0000 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
N2 C2 N3 . . 120.53(10) ?
N2 C2 N1 . . 116.70(10) ?
N3 C2 N1 . . 122.76(10) ?
N4 C4 N3 . . 116.01(10) ?
N4 C4 C5 . . 121.20(10) ?
N3 C4 C5 . . 122.78(10) ?
C6 C5 C4 . . 117.60(10) ?
C6 C5 H5 . . 121.2 ?
C4 C5 H5 . . 121.2 ?
N5 C6 N1 . . 116.70(10) ?
N5 C6 C5 . . 124.26(10) ?
N1 C6 C5 . . 119.05(10) ?
O1 C7 O2 . . 124.34(10) ?
O1 C7 C8 . . 119.15(10) ?
O2 C7 C8 . . 116.49(10) ?
C9 C8 C7 . . 123.48(10) ?
C9 C8 H8 . . 118.3 ?
C7 C8 H8 . . 118.3 ?
C8 C9 C10 . . 123.72(11) ?
C8 C9 H9 . . 118.1 ?
C10 C9 H9 . . 118.1 ?
C11 C10 C9 . . 123.48(11) ?
C11 C10 H10 . . 118.3 ?
C9 C10 H10 . . 118.3 ?
C10 C11 C12 . . 124.89(11) ?
C10 C11 H11 . . 117.6 ?
C12 C11 H11 . . 117.6 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 N1 C6 . . 120.54(10) ?
C2 N1 H1 . . 118.3(13) ?
C6 N1 H1 . . 121.2(13) ?
C2 N2 H2A . . 117.8(13) ?
C2 N2 H2B . . 120.1(12) ?
H2A N2 H2B . . 121.1(17) ?
C2 N3 C4 . . 117.28(10) ?
C4 N4 H4A . . 118.7(12) ?
C4 N4 H4B . . 119.0(13) ?
H4A N4 H4B . . 120.1(18) ?
C6 N5 H5A . . 119.4(14) ?
C6 N5 H5B . . 116.2(12) ?
H5A N5 H5B . . 124.4(18) ?
H1WA O1W H1WB . . 108(2) ?
H2WA O2W H2WB . . 107(2) ?
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 N2 . 1.3312(14) ?
C2 N3 . 1.3318(14) ?
C2 N1 . 1.3661(14) ?
C4 N4 . 1.3397(14) ?
C4 N3 . 1.3615(14) ?
C4 C5 . 1.4044(15) ?
C5 C6 . 1.3804(15) ?
C5 H5 . 0.9500 ?
C6 N5 . 1.3441(15) ?
C6 N1 . 1.3678(14) ?
C7 O1 . 1.2638(14) ?
C7 O2 . 1.2726(14) ?
C7 C8 . 1.4879(15) ?
C8 C9 . 1.3384(16) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.4535(16) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3376(17) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.4963(16) ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
N1 H1 . 0.97(2) ?
N2 H2A . 0.85(2) ?
N2 H2B . 0.895(19) ?
N4 H4A . 0.88(2) ?
N4 H4B . 0.87(2) ?
N5 H5A . 0.90(2) ?
N5 H5B . 0.842(19) ?
O1W H1WA . 0.87(3) ?
O1W H1WB . 0.82(2) ?
O2W H2WA . 0.87(3) ?
O2W H2WB . 0.91(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 O1 . 0.97(2) 1.74(2) 2.7053(13) 175(2) yes
N2 H2A O2W . 0.85(2) 2.08(2) 2.9270(14) 176.8(19) yes
N2 H2B O2 . 0.895(19) 1.959(19) 2.8529(13) 176.4(17) yes
N4 H4A O1W 2_556 0.88(2) 2.130(19) 2.9210(14) 149.0(17) yes
N4 H4B O2W 1_455 0.87(2) 2.01(2) 2.8695(14) 171.3(18) yes
N5 H5B O2 1_455 0.842(19) 2.09(2) 2.9299(14) 174.6(18) yes
O1W H1WA O1 1_545 0.87(3) 2.00(3) 2.8159(14) 156(2) yes
O1W H1WB N3 . 0.82(2) 2.03(2) 2.8444(14) 173(2) yes
O2W H2WA O2 2_666 0.87(3) 1.94(3) 2.8021(14) 169(2) yes
O2W H2WB O1W . 0.91(3) 1.86(3) 2.7558(14) 169(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 . . . . 178.85(11) ?
N3 C4 C5 C6 . . . . 0.14(18) ?
C4 C5 C6 N5 . . . . 179.93(12) ?
C4 C5 C6 N1 . . . . 0.08(18) ?
O1 C7 C8 C9 . . . . 22.24(19) ?
O2 C7 C8 C9 . . . . -159.48(12) ?
C7 C8 C9 C10 . . . . -177.74(11) ?
C8 C9 C10 C11 . . . . -178.77(13) ?
C9 C10 C11 C12 . . . . -177.64(12) ?
N2 C2 N1 C6 . . . . -179.44(11) ?
N3 C2 N1 C6 . . . . -0.46(18) ?
N5 C6 N1 C2 . . . . -179.80(11) ?
C5 C6 N1 C2 . . . . 0.07(18) ?
N2 C2 N3 C4 . . . . 179.60(11) ?
N1 C2 N3 C4 . . . . 0.65(17) ?
N4 C4 N3 C2 . . . . -179.27(11) ?
C5 C4 N3 C2 . . . . -0.50(18) ?
