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

Three salts, namely, 2,4,6-tri­amino­pyrimidin-1-ium sorbate dihydrate, C₄H₈N₅⁺·C₆H₇O₂⁻·2H₂O, (I), 2,4,6-tri­amino­pyrimidin-1-ium N-phenyl­anthranilate, C₄H₈N₅⁺·C₁₃H₁₀NO₂⁻, (II), and 2,4,6-tri­amino­pyrimidin-1-ium p-toluene­sul­fon­ate, C₄H₈N₅⁺·C₇H₇O₃S⁻, (III), were synthesized, characterized by X-ray diffraction techniques and their supra­molecular inter­actions investigated. In all three crystal structures, protonation of the pyrimidine moiety occurs at the N1 position and is reflected in a widening of the C—N—C bond angle. In salts (I)–(III), the primary acid–base inter­action occurs through a pair of N—H...O hy­dro­gen bonds to give a heterodimeric R₂²(8) synthon. Salts (II) and (III) form a discrete centrosymmetric base pair that produces a homodimeric R₂²(8) synthon and salt (I) forms a water-mediated base pair resulting in a tetrameric R₄⁴(12) synthon. The supra­molecular patterns exhibited by sulfonate salt (III) mimic the patterns of carboxyl­ate salt (II) and both exhibit a DADA array (D = donor and A = acceptor) quadruple hy­dro­gen-bonded pattern. The crystal structures of salts (I) and (III) are stabilized by offset and face-to-face aromatic π–π stacking inter­actions, respectively. The resulting architectures in salts (I)–(III) are a supra­molecular sheet with a rosette-like architecture in (I), a supra­molecular sheet-like architecture in (II) and a three-dimensional supramolecular network in (III).

Computing details

2,4,6-Triaminopyrimidin-1-ium 2,4-hexadienoate dihydrate (I)

Crystal data

C4H8N5^+·C6H7O2^−·2H2O	Z = 2
Mr = 273.30	F(000) = 292
Triclinic, P1	Dx = 1.347 Mg m^−3
a = 8.2507 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5870 (4) Å	Cell parameters from 3922 reflections
c = 10.6398 (5) Å	θ = 2.5–30.5°
α = 105.438 (2)°	µ = 0.11 mm^−1
β = 109.180 (2)°	T = 120 K
γ = 94.887 (2)°	Plate, colourless
V = 673.83 (6) Å^3	0.25 × 0.24 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	3350 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
ω scans	θmax = 30.6°, θmin = 2.5°
Absorption correction: analytical (SADABS; Krause et al., 2015)	h = −11→11
Tmin = 0.974, Tmax = 0.992	k = −10→12
11015 measured reflections	l = −15→14
3920 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: mixed
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.056P)^2 + 0.3374P] where P = (Fo^2 + 2Fc^2)/3
3920 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All hydrogen-bond H atoms were refined freely. All others were idealized.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.21036 (14)	0.52917 (14)	0.67628 (12)	0.0125 (2)
C4	−0.06518 (14)	0.39295 (14)	0.63045 (12)	0.0125 (2)
C5	−0.11729 (14)	0.54083 (14)	0.68159 (13)	0.0134 (2)
H5	−0.232072	0.541824	0.682225	0.016*
C6	0.00428 (15)	0.68470 (14)	0.73091 (13)	0.0132 (2)
C7	0.55092 (15)	0.96261 (14)	0.80555 (12)	0.0131 (2)
C8	0.66259 (15)	1.12423 (14)	0.83778 (13)	0.0155 (2)
H8	0.749630	1.127380	0.797690	0.019*
C9	0.64693 (15)	1.26541 (14)	0.92026 (13)	0.0148 (2)
H9	0.562729	1.261439	0.962998	0.018*
C10	0.75145 (15)	1.42448 (14)	0.94814 (13)	0.0155 (2)
H10	0.834099	1.429008	0.904022	0.019*
C11	0.73742 (15)	1.56481 (14)	1.03264 (13)	0.0155 (2)
H11	0.657594	1.558288	1.079028	0.019*
C12	0.83806 (16)	1.73131 (14)	1.05957 (14)	0.0176 (2)
H12A	0.910513	1.721961	1.002072	0.026*
H12B	0.913077	1.776338	1.158838	0.026*
H12C	0.756500	1.804669	1.035437	0.026*
N1	0.16783 (12)	0.67700 (12)	0.72768 (11)	0.0126 (2)
H1	0.257 (3)	0.776 (3)	0.763 (2)	0.039 (5)*
N2	0.37270 (13)	0.53244 (13)	0.67802 (12)	0.0158 (2)
H2A	0.397 (3)	0.444 (2)	0.636 (2)	0.028 (5)*
H2B	0.447 (2)	0.629 (2)	0.708 (2)	0.024 (4)*
N3	0.09825 (12)	0.38690 (12)	0.62823 (11)	0.0130 (2)
N4	−0.17461 (14)	0.24794 (13)	0.58301 (12)	0.0163 (2)
H4A	−0.144 (3)	0.160 (2)	0.540 (2)	0.028 (5)*
H4B	−0.283 (3)	0.247 (2)	0.575 (2)	0.027 (5)*
N5	−0.02680 (14)	0.83504 (13)	0.78272 (13)	0.0184 (2)
H5A	0.057 (3)	0.924 (3)	0.810 (2)	0.037 (5)*
H5B	−0.128 (3)	0.839 (2)	0.7827 (19)	0.023 (4)*
O1	0.40374 (11)	0.95944 (10)	0.81822 (10)	0.01632 (19)
O2	0.61058 (11)	0.83513 (11)	0.76303 (10)	0.01683 (19)
O1W	0.21817 (12)	0.08333 (11)	0.60438 (11)	0.0188 (2)
H1WA	0.273 (3)	0.072 (3)	0.686 (3)	0.041 (6)*
H1WB	0.180 (3)	0.170 (3)	0.617 (2)	0.035 (5)*
O2W	0.45831 (12)	0.23431 (12)	0.52425 (11)	0.0195 (2)
H2WA	0.424 (3)	0.206 (3)	0.434 (3)	0.049 (6)*
H2WB	0.383 (3)	0.171 (3)	0.545 (3)	0.050 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0117 (5)	0.0125 (5)	0.0134 (5)	0.0020 (4)	0.0047 (4)	0.0044 (4)
C4	0.0113 (5)	0.0127 (5)	0.0134 (5)	0.0011 (4)	0.0040 (4)	0.0050 (4)
C5	0.0109 (5)	0.0129 (5)	0.0169 (5)	0.0018 (4)	0.0057 (4)	0.0048 (4)
C6	0.0124 (5)	0.0132 (5)	0.0150 (5)	0.0028 (4)	0.0056 (4)	0.0052 (4)
C7	0.0126 (5)	0.0126 (5)	0.0128 (5)	0.0010 (4)	0.0035 (4)	0.0036 (4)
C8	0.0133 (5)	0.0145 (5)	0.0190 (6)	0.0009 (4)	0.0069 (4)	0.0053 (4)
C9	0.0130 (5)	0.0137 (5)	0.0166 (5)	0.0006 (4)	0.0046 (4)	0.0047 (4)
C10	0.0141 (5)	0.0148 (5)	0.0171 (6)	0.0006 (4)	0.0053 (4)	0.0053 (4)
C11	0.0135 (5)	0.0150 (5)	0.0161 (5)	0.0004 (4)	0.0032 (4)	0.0055 (4)
C12	0.0181 (5)	0.0128 (5)	0.0198 (6)	0.0008 (4)	0.0055 (5)	0.0042 (4)
N1	0.0109 (4)	0.0110 (4)	0.0158 (5)	0.0012 (3)	0.0056 (4)	0.0034 (4)
N2	0.0117 (4)	0.0134 (5)	0.0224 (5)	0.0019 (3)	0.0083 (4)	0.0032 (4)
N3	0.0113 (4)	0.0121 (4)	0.0152 (5)	0.0012 (3)	0.0054 (4)	0.0034 (4)
N4	0.0126 (4)	0.0116 (4)	0.0229 (5)	−0.0003 (3)	0.0075 (4)	0.0020 (4)
N5	0.0143 (5)	0.0123 (5)	0.0282 (6)	0.0023 (4)	0.0098 (4)	0.0036 (4)
O1	0.0128 (4)	0.0144 (4)	0.0212 (5)	0.0011 (3)	0.0071 (3)	0.0040 (3)
O2	0.0148 (4)	0.0133 (4)	0.0215 (5)	0.0024 (3)	0.0072 (3)	0.0035 (3)
O1W	0.0187 (4)	0.0150 (4)	0.0217 (5)	0.0060 (3)	0.0063 (4)	0.0046 (3)
O2W	0.0167 (4)	0.0207 (4)	0.0204 (5)	0.0025 (3)	0.0085 (4)	0.0035 (4)

Geometric parameters (Å, º)

C2—N2	1.3312 (14)	C10—H10	0.9500
C2—N3	1.3318 (14)	C11—C12	1.4963 (16)
C2—N1	1.3661 (14)	C11—H11	0.9500
C4—N4	1.3397 (14)	C12—H12A	0.9800
C4—N3	1.3615 (14)	C12—H12B	0.9800
C4—C5	1.4044 (15)	C12—H12C	0.9800
C5—C6	1.3804 (15)	N1—H1	0.97 (2)
C5—H5	0.9500	N2—H2A	0.85 (2)
C6—N5	1.3441 (15)	N2—H2B	0.895 (19)
C6—N1	1.3678 (14)	N4—H4A	0.88 (2)
C7—O1	1.2638 (14)	N4—H4B	0.87 (2)
C7—O2	1.2726 (14)	N5—H5A	0.90 (2)
C7—C8	1.4879 (15)	N5—H5B	0.842 (19)
C8—C9	1.3384 (16)	O1W—H1WA	0.87 (3)
C8—H8	0.9500	O1W—H1WB	0.82 (2)
C9—C10	1.4535 (16)	O2W—H2WA	0.87 (3)
C9—H9	0.9500	O2W—H2WB	0.91 (3)
C10—C11	1.3376 (17)
N2—C2—N3	120.53 (10)	C10—C11—C12	124.89 (11)
N2—C2—N1	116.70 (10)	C10—C11—H11	117.6
N3—C2—N1	122.76 (10)	C12—C11—H11	117.6
N4—C4—N3	116.01 (10)	C11—C12—H12A	109.5
N4—C4—C5	121.20 (10)	C11—C12—H12B	109.5
N3—C4—C5	122.78 (10)	H12A—C12—H12B	109.5
C6—C5—C4	117.60 (10)	C11—C12—H12C	109.5
C6—C5—H5	121.2	H12A—C12—H12C	109.5
C4—C5—H5	121.2	H12B—C12—H12C	109.5
N5—C6—N1	116.70 (10)	C2—N1—C6	120.54 (10)
N5—C6—C5	124.26 (10)	C2—N1—H1	118.3 (13)
N1—C6—C5	119.05 (10)	C6—N1—H1	121.2 (13)
O1—C7—O2	124.34 (10)	C2—N2—H2A	117.8 (13)
O1—C7—C8	119.15 (10)	C2—N2—H2B	120.1 (12)
O2—C7—C8	116.49 (10)	H2A—N2—H2B	121.1 (17)
C9—C8—C7	123.48 (10)	C2—N3—C4	117.28 (10)
C9—C8—H8	118.3	C4—N4—H4A	118.7 (12)
C7—C8—H8	118.3	C4—N4—H4B	119.0 (13)
C8—C9—C10	123.72 (11)	H4A—N4—H4B	120.1 (18)
C8—C9—H9	118.1	C6—N5—H5A	119.4 (14)
C10—C9—H9	118.1	C6—N5—H5B	116.2 (12)
C11—C10—C9	123.48 (11)	H5A—N5—H5B	124.4 (18)
C11—C10—H10	118.3	H1WA—O1W—H1WB	108 (2)
C9—C10—H10	118.3	H2WA—O2W—H2WB	107 (2)
N4—C4—C5—C6	178.85 (11)	N2—C2—N1—C6	−179.44 (11)
N3—C4—C5—C6	0.14 (18)	N3—C2—N1—C6	−0.46 (18)
C4—C5—C6—N5	179.93 (12)	N5—C6—N1—C2	−179.80 (11)
C4—C5—C6—N1	0.08 (18)	C5—C6—N1—C2	0.07 (18)
O1—C7—C8—C9	22.24 (19)	N2—C2—N3—C4	179.60 (11)
O2—C7—C8—C9	−159.48 (12)	N1—C2—N3—C4	0.65 (17)
C7—C8—C9—C10	−177.74 (11)	N4—C4—N3—C2	−179.27 (11)
C8—C9—C10—C11	−178.77 (13)	C5—C4—N3—C2	−0.50 (18)
C9—C10—C11—C12	−177.64 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.97 (2)	1.74 (2)	2.7053 (13)	175 (2)
N2—H2A···O2W	0.85 (2)	2.08 (2)	2.9270 (14)	176.8 (19)
N2—H2B···O2	0.895 (19)	1.959 (19)	2.8529 (13)	176.4 (17)
N4—H4A···O1W^i	0.88 (2)	2.130 (19)	2.9210 (14)	149.0 (17)
N4—H4B···O2W^ii	0.87 (2)	2.01 (2)	2.8695 (14)	171.3 (18)
N5—H5B···O2^ii	0.842 (19)	2.09 (2)	2.9299 (14)	174.6 (18)
O1W—H1WA···O1^iii	0.87 (3)	2.00 (3)	2.8159 (14)	156 (2)
O1W—H1WB···N3	0.82 (2)	2.03 (2)	2.8444 (14)	173 (2)
O2W—H2WA···O2^iv	0.87 (3)	1.94 (3)	2.8021 (14)	169 (2)
O2W—H2WB···O1W	0.91 (3)	1.86 (3)	2.7558 (14)	169 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y, z; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1.

2,4,6-Triaminopyrimidin-1-ium 2-(phenylamino)benzoate (II)

Crystal data

C4H8N5^+·C13H10NO2^−	F(000) = 1424
Mr = 338.37	Dx = 1.422 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 13.1498 (8) Å	Cell parameters from 10186 reflections
b = 12.1582 (6) Å	θ = 2.8–41.3°
c = 20.6224 (10) Å	µ = 0.10 mm^−1
β = 106.538 (5)°	T = 120 K
V = 3160.7 (3) Å^3	Block, colourless
Z = 8	0.48 × 0.23 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	3887 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2961 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.053
ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −16→17
Tmin = 0.954, Tmax = 0.988	k = −16→16
10681 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: mixed
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0304P)^2 + 4.6822P] where P = (Fo^2 + 2Fc^2)/3
3887 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.35 e Å^−3
4 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms potentially involved in hydrogen-bonding were refined isotropically while all other H atoms were idealized.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.44515 (14)	0.08042 (14)	0.57748 (8)	0.0147 (3)
C4	0.56213 (14)	−0.01785 (15)	0.66021 (8)	0.0156 (4)
C5	0.53192 (14)	0.03861 (15)	0.71079 (9)	0.0173 (4)
H5	0.562344	0.021014	0.757159	0.021*
C6	0.45743 (14)	0.11981 (15)	0.69180 (8)	0.0163 (4)
C7	0.11145 (15)	0.38971 (15)	0.61560 (8)	0.0169 (4)
C8	0.10240 (15)	0.50179 (16)	0.63149 (9)	0.0187 (4)
C9	0.00131 (16)	0.54770 (17)	0.61769 (10)	0.0225 (4)
H9	−0.005746	0.623091	0.627718	0.027*
C10	−0.08837 (16)	0.48641 (18)	0.58992 (10)	0.0246 (4)
H10	−0.156275	0.519929	0.580516	0.030*
C11	−0.08022 (16)	0.37615 (17)	0.57559 (9)	0.0222 (4)
H11	−0.142167	0.333138	0.557633	0.027*
C12	0.01937 (15)	0.32935 (16)	0.58777 (9)	0.0188 (4)
H12	0.025067	0.254113	0.576869	0.023*
C13	0.21578 (15)	0.33173 (15)	0.63012 (8)	0.0162 (4)
C14	0.20922 (15)	0.67250 (15)	0.64340 (9)	0.0190 (4)
C15	0.29173 (16)	0.73194 (17)	0.68571 (10)	0.0230 (4)
H15	0.330860	0.701414	0.727833	0.028*
C16	0.31760 (17)	0.83506 (18)	0.66724 (11)	0.0288 (5)
H16	0.374651	0.874727	0.696546	0.035*
C17	0.26074 (18)	0.88100 (18)	0.60617 (12)	0.0297 (5)
H17	0.278670	0.951779	0.593266	0.036*
C18	0.17806 (17)	0.82275 (17)	0.56452 (11)	0.0256 (4)
H18	0.138912	0.853751	0.522547	0.031*
C19	0.15096 (16)	0.71978 (16)	0.58272 (10)	0.0219 (4)
H19	0.092593	0.681309	0.553823	0.026*
N1	0.41434 (12)	0.14070 (12)	0.62432 (7)	0.0151 (3)
H1	0.3575 (17)	0.1892 (18)	0.6107 (10)	0.015 (5)*
N2	0.39847 (13)	0.10306 (14)	0.51263 (7)	0.0186 (3)
H2A	0.3639 (18)	0.1636 (16)	0.5000 (12)	0.028 (6)*
H2B	0.4217 (18)	0.0658 (19)	0.4828 (11)	0.030 (6)*
N3	0.51713 (12)	0.00197 (13)	0.59342 (7)	0.0154 (3)
N4	0.63787 (13)	−0.09401 (13)	0.67571 (8)	0.0190 (3)
H4A	0.6723 (17)	−0.1055 (19)	0.7177 (8)	0.025 (6)*
H4B	0.6599 (18)	−0.1235 (19)	0.6437 (10)	0.027 (6)*
N5	0.42206 (15)	0.18231 (15)	0.73387 (8)	0.0237 (4)
H5A	0.448 (2)	0.172 (2)	0.7764 (13)	0.033 (7)*
H5B	0.380 (2)	0.241 (3)	0.7177 (14)	0.054 (9)*
N6	0.19120 (14)	0.56471 (14)	0.66224 (8)	0.0211 (3)
H6	0.253 (2)	0.525 (2)	0.6822 (13)	0.036 (7)*
O1	0.29001 (11)	0.36318 (11)	0.67998 (6)	0.0195 (3)
O2	0.22436 (10)	0.25204 (11)	0.59280 (6)	0.0183 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0159 (8)	0.0156 (8)	0.0131 (8)	−0.0019 (7)	0.0050 (6)	−0.0006 (6)
C4	0.0174 (9)	0.0162 (9)	0.0128 (8)	−0.0017 (7)	0.0038 (6)	0.0016 (6)
C5	0.0207 (9)	0.0200 (9)	0.0105 (8)	0.0012 (7)	0.0032 (7)	0.0004 (7)
C6	0.0186 (9)	0.0179 (9)	0.0133 (8)	−0.0042 (7)	0.0061 (7)	−0.0010 (6)
C7	0.0217 (9)	0.0195 (9)	0.0108 (8)	0.0011 (7)	0.0068 (7)	0.0012 (6)
C8	0.0226 (9)	0.0217 (9)	0.0134 (8)	−0.0019 (7)	0.0076 (7)	−0.0002 (7)
C9	0.0266 (10)	0.0202 (10)	0.0236 (9)	0.0034 (8)	0.0118 (8)	−0.0009 (7)
C10	0.0205 (10)	0.0304 (11)	0.0254 (10)	0.0036 (8)	0.0104 (8)	0.0003 (8)
C11	0.0202 (9)	0.0279 (11)	0.0204 (9)	−0.0034 (8)	0.0091 (7)	−0.0025 (8)
C12	0.0229 (10)	0.0202 (9)	0.0146 (8)	0.0000 (7)	0.0072 (7)	−0.0010 (7)
C13	0.0206 (9)	0.0166 (9)	0.0121 (8)	−0.0028 (7)	0.0059 (7)	0.0016 (6)
C14	0.0214 (9)	0.0171 (9)	0.0208 (9)	−0.0022 (7)	0.0098 (7)	−0.0036 (7)
C15	0.0242 (10)	0.0231 (10)	0.0221 (9)	−0.0044 (8)	0.0074 (8)	−0.0049 (8)
C16	0.0264 (11)	0.0256 (11)	0.0362 (12)	−0.0057 (9)	0.0118 (9)	−0.0073 (9)
C17	0.0329 (12)	0.0198 (10)	0.0424 (13)	0.0002 (9)	0.0206 (10)	0.0021 (9)
C18	0.0264 (11)	0.0251 (11)	0.0290 (10)	0.0036 (8)	0.0141 (8)	0.0058 (8)
C19	0.0248 (10)	0.0222 (10)	0.0204 (9)	−0.0014 (8)	0.0092 (8)	−0.0016 (7)
N1	0.0183 (8)	0.0148 (7)	0.0125 (7)	0.0028 (6)	0.0049 (6)	0.0008 (5)
N2	0.0233 (8)	0.0214 (8)	0.0110 (7)	0.0072 (7)	0.0046 (6)	0.0020 (6)
N3	0.0188 (8)	0.0169 (7)	0.0108 (7)	0.0021 (6)	0.0047 (6)	0.0010 (5)
N4	0.0248 (8)	0.0197 (8)	0.0113 (7)	0.0049 (7)	0.0035 (6)	0.0015 (6)
N5	0.0310 (10)	0.0278 (9)	0.0124 (8)	0.0094 (8)	0.0065 (7)	−0.0006 (7)
N6	0.0231 (9)	0.0182 (8)	0.0199 (8)	−0.0025 (7)	0.0025 (6)	−0.0009 (6)
O1	0.0223 (7)	0.0191 (7)	0.0146 (6)	−0.0012 (5)	0.0013 (5)	−0.0023 (5)
O2	0.0209 (7)	0.0184 (7)	0.0154 (6)	0.0004 (5)	0.0047 (5)	−0.0033 (5)

Geometric parameters (Å, º)

C2—N3	1.318 (2)	C13—O1	1.259 (2)
C2—N2	1.332 (2)	C13—O2	1.262 (2)
C2—N1	1.363 (2)	C14—C15	1.386 (3)
C4—N4	1.331 (2)	C14—C19	1.392 (3)
C4—N3	1.357 (2)	C14—N6	1.406 (2)
C4—C5	1.397 (2)	C15—C16	1.381 (3)
C5—C6	1.367 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.386 (3)
C6—N5	1.333 (2)	C16—H16	0.9500
C6—N1	1.369 (2)	C17—C18	1.375 (3)
C7—C12	1.392 (3)	C17—H17	0.9500
C7—C8	1.414 (3)	C18—C19	1.383 (3)
C7—C13	1.495 (3)	C18—H18	0.9500
C8—N6	1.389 (2)	C19—H19	0.9500
C8—C9	1.394 (3)	N1—H1	0.93 (2)
C9—C10	1.375 (3)	N2—H2A	0.865 (16)
C9—H9	0.9500	N2—H2B	0.884 (16)
C10—C11	1.383 (3)	N4—H4A	0.866 (16)
C10—H10	0.9500	N4—H4B	0.869 (16)
C11—C12	1.384 (3)	N5—H5A	0.85 (3)
C11—H11	0.9500	N5—H5B	0.91 (3)
C12—H12	0.9500	N6—H6	0.93 (3)
N3—C2—N2	119.53 (16)	C15—C14—N6	118.37 (18)
N3—C2—N1	123.36 (15)	C19—C14—N6	122.71 (17)
N2—C2—N1	117.10 (16)	C16—C15—C14	120.7 (2)
N4—C4—N3	116.60 (15)	C16—C15—H15	119.7
N4—C4—C5	120.99 (16)	C14—C15—H15	119.7
N3—C4—C5	122.41 (16)	C15—C16—C17	120.3 (2)
C6—C5—C4	118.27 (16)	C15—C16—H16	119.8
C6—C5—H5	120.9	C17—C16—H16	119.8
C4—C5—H5	120.9	C18—C17—C16	119.1 (2)
N5—C6—C5	125.42 (17)	C18—C17—H17	120.5
N5—C6—N1	115.84 (17)	C16—C17—H17	120.5
C5—C6—N1	118.74 (16)	C17—C18—C19	121.1 (2)
C12—C7—C8	118.86 (17)	C17—C18—H18	119.5
C12—C7—C13	118.35 (16)	C19—C18—H18	119.5
C8—C7—C13	122.74 (17)	C18—C19—C14	119.97 (19)
N6—C8—C9	120.09 (17)	C18—C19—H19	120.0
N6—C8—C7	121.41 (17)	C14—C19—H19	120.0
C9—C8—C7	118.46 (18)	C2—N1—C6	120.02 (15)
C10—C9—C8	121.53 (18)	C2—N1—H1	120.2 (12)
C10—C9—H9	119.2	C6—N1—H1	119.3 (12)
C8—C9—H9	119.2	C2—N2—H2A	122.0 (16)
C9—C10—C11	120.32 (18)	C2—N2—H2B	116.1 (16)
C9—C10—H10	119.8	H2A—N2—H2B	119 (2)
C11—C10—H10	119.8	C2—N3—C4	117.15 (15)
C10—C11—C12	119.11 (18)	C4—N4—H4A	119.7 (16)
C10—C11—H11	120.4	C4—N4—H4B	119.5 (16)
C12—C11—H11	120.4	H4A—N4—H4B	120 (2)
C11—C12—C7	121.68 (18)	C6—N5—H5A	118.3 (17)
C11—C12—H12	119.2	C6—N5—H5B	120.0 (18)
C7—C12—H12	119.2	H5A—N5—H5B	121 (2)
O1—C13—O2	123.23 (17)	C8—N6—C14	124.96 (17)
O1—C13—C7	118.32 (16)	C8—N6—H6	115.0 (16)
O2—C13—C7	118.43 (16)	C14—N6—H6	114.6 (16)
C15—C14—C19	118.85 (18)
N4—C4—C5—C6	176.75 (17)	N6—C14—C15—C16	175.33 (18)
N3—C4—C5—C6	−2.8 (3)	C14—C15—C16—C17	0.5 (3)
C4—C5—C6—N5	−178.57 (18)	C15—C16—C17—C18	0.3 (3)
C4—C5—C6—N1	1.3 (3)	C16—C17—C18—C19	0.1 (3)
C12—C7—C8—N6	176.95 (16)	C17—C18—C19—C14	−1.4 (3)
C13—C7—C8—N6	−0.4 (3)	C15—C14—C19—C18	2.2 (3)
C12—C7—C8—C9	−0.9 (2)	N6—C14—C19—C18	−174.73 (17)
C13—C7—C8—C9	−178.22 (16)	N3—C2—N1—C6	−1.1 (3)
N6—C8—C9—C10	−177.23 (17)	N2—C2—N1—C6	178.48 (16)
C7—C8—C9—C10	0.6 (3)	N5—C6—N1—C2	−179.57 (17)
C8—C9—C10—C11	0.8 (3)	C5—C6—N1—C2	0.6 (3)
C9—C10—C11—C12	−1.9 (3)	N2—C2—N3—C4	−179.92 (16)
C10—C11—C12—C7	1.6 (3)	N1—C2—N3—C4	−0.4 (3)
C8—C7—C12—C11	−0.2 (3)	N4—C4—N3—C2	−177.25 (16)
C13—C7—C12—C11	177.23 (16)	C5—C4—N3—C2	2.3 (3)
C12—C7—C13—O1	−147.40 (17)	C9—C8—N6—C14	−46.2 (3)
C8—C7—C13—O1	29.9 (2)	C7—C8—N6—C14	136.03 (19)
C12—C7—C13—O2	31.0 (2)	C15—C14—N6—C8	168.98 (17)
C8—C7—C13—O2	−151.69 (17)	C19—C14—N6—C8	−14.1 (3)
C19—C14—C15—C16	−1.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93 (2)	1.85 (2)	2.752 (2)	162.9 (19)
N2—H2A···O2^i	0.87 (2)	2.21 (2)	2.936 (2)	141 (2)
N2—H2B···N3^ii	0.88 (2)	2.13 (2)	3.004 (2)	172 (2)
N4—H4A···O1^iii	0.87 (2)	2.06 (2)	2.902 (2)	163 (2)
N4—H4B···O2^iv	0.87 (2)	2.19 (2)	3.003 (2)	157 (2)
N5—H5B···O1	0.91 (3)	1.92 (3)	2.826 (2)	178 (3)
N6—H6···O1	0.93 (3)	2.03 (3)	2.749 (2)	133 (2)

Symmetry codes: (i) −x+1/2, y, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1/2, −y, z.

2,4,6-Triaminopyrimidin-1-ium 4-methylbenzene-1-sulfonate (III)

Crystal data

C4H8N5^+·C7H7O3S^−	Z = 2
Mr = 297.34	F(000) = 312
Triclinic, P1	Dx = 1.445 Mg m^−3
a = 6.8382 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3657 (4) Å	Cell parameters from 3958 reflections
c = 12.5848 (6) Å	θ = 2.9–30.6°
α = 92.727 (1)°	µ = 0.25 mm^−1
β = 104.992 (2)°	T = 120 K
γ = 99.194 (1)°	Plate, colourless
V = 683.50 (6) Å^3	0.25 × 0.24 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	3406 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
ω scans	θmax = 30.6°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
Tmin = 0.974, Tmax = 0.992	k = −9→11
11436 measured reflections	l = −17→17
3956 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0273P)^2 + 0.6477P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3956 reflections	Δρmax = 0.45 e Å^−3
210 parameters	Δρmin = −0.55 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms potentially involved in hydrogen-bonding were refined isotropically. All others were idealized.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	1.0429 (2)	0.83514 (16)	0.87921 (12)	0.0145 (3)
C4	1.2182 (2)	1.09792 (16)	0.91876 (11)	0.0138 (2)
C5	1.0367 (2)	1.16001 (16)	0.87605 (12)	0.0151 (3)
H5	1.039298	1.273782	0.874923	0.018*
C6	0.8560 (2)	1.05093 (17)	0.83608 (12)	0.0146 (3)
C7	0.2863 (2)	0.40082 (17)	0.65470 (12)	0.0163 (3)
C8	0.3609 (2)	0.3423 (2)	0.57086 (15)	0.0276 (4)
H8	0.504174	0.364419	0.576722	0.033*
C9	0.2250 (3)	0.2508 (2)	0.47803 (15)	0.0291 (4)
H9	0.276541	0.211659	0.420465	0.035*
C10	0.0145 (2)	0.21581 (19)	0.46832 (13)	0.0202 (3)
C11	−0.0578 (2)	0.2802 (2)	0.55142 (14)	0.0230 (3)
H11	−0.201413	0.260999	0.544531	0.028*
C12	0.0758 (2)	0.3725 (2)	0.64476 (13)	0.0213 (3)
H12	0.023763	0.415572	0.700923	0.026*
C13	−0.1331 (3)	0.1118 (2)	0.36963 (14)	0.0261 (3)
H13A	−0.247173	0.049978	0.392481	0.039*
H13B	−0.060662	0.036331	0.339597	0.039*
H13C	−0.186955	0.181648	0.312840	0.039*
N1	0.86210 (18)	0.88856 (14)	0.83890 (10)	0.0148 (2)
H1	0.746 (4)	0.816 (3)	0.8115 (19)	0.035 (6)*
N2	1.0342 (2)	0.67449 (15)	0.87713 (12)	0.0200 (3)
H2A	1.150 (3)	0.638 (3)	0.8915 (18)	0.027 (5)*
H2B	0.914 (3)	0.610 (3)	0.8494 (18)	0.029 (5)*
N3	1.22126 (17)	0.93536 (14)	0.91941 (10)	0.0145 (2)
N4	1.39760 (19)	1.19630 (15)	0.96345 (11)	0.0180 (2)
H4A	1.507 (3)	1.158 (3)	0.9955 (18)	0.030 (6)*
H4B	1.408 (3)	1.298 (3)	0.9605 (18)	0.025 (5)*
N5	0.6701 (2)	1.08955 (16)	0.79206 (12)	0.0204 (3)
H5A	0.557 (3)	1.016 (3)	0.7800 (18)	0.030 (6)*
H5B	0.659 (3)	1.188 (3)	0.7960 (17)	0.022 (5)*
O1	0.50204 (16)	0.68142 (13)	0.74340 (10)	0.0217 (2)
O2	0.35876 (16)	0.50318 (12)	0.86189 (9)	0.0178 (2)
O3	0.64561 (15)	0.44096 (13)	0.79621 (10)	0.0203 (2)
S1	0.46003 (5)	0.51457 (4)	0.77291 (3)	0.01580 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0137 (6)	0.0115 (6)	0.0175 (6)	0.0025 (4)	0.0031 (5)	0.0003 (5)
C4	0.0144 (6)	0.0124 (6)	0.0146 (6)	0.0012 (4)	0.0048 (5)	0.0006 (5)
C5	0.0148 (6)	0.0111 (6)	0.0189 (6)	0.0026 (5)	0.0037 (5)	0.0010 (5)
C6	0.0146 (6)	0.0131 (6)	0.0163 (6)	0.0040 (5)	0.0038 (5)	0.0006 (5)
C7	0.0149 (6)	0.0136 (6)	0.0194 (7)	0.0022 (5)	0.0028 (5)	0.0019 (5)
C8	0.0174 (7)	0.0363 (9)	0.0286 (8)	0.0017 (6)	0.0090 (6)	−0.0058 (7)
C9	0.0255 (8)	0.0379 (10)	0.0243 (8)	0.0049 (7)	0.0099 (6)	−0.0069 (7)
C10	0.0233 (7)	0.0190 (7)	0.0169 (7)	0.0052 (5)	0.0019 (5)	0.0028 (5)
C11	0.0145 (6)	0.0281 (8)	0.0233 (7)	0.0026 (6)	0.0016 (5)	−0.0036 (6)
C12	0.0165 (6)	0.0240 (7)	0.0222 (7)	0.0026 (5)	0.0047 (5)	−0.0046 (6)
C13	0.0284 (8)	0.0271 (8)	0.0191 (7)	0.0062 (6)	−0.0004 (6)	−0.0018 (6)
N1	0.0112 (5)	0.0115 (5)	0.0199 (6)	0.0016 (4)	0.0017 (4)	−0.0004 (4)
N2	0.0141 (6)	0.0110 (5)	0.0326 (7)	0.0025 (4)	0.0023 (5)	−0.0005 (5)
N3	0.0129 (5)	0.0112 (5)	0.0180 (6)	0.0015 (4)	0.0026 (4)	0.0001 (4)
N4	0.0139 (5)	0.0110 (5)	0.0265 (7)	0.0005 (4)	0.0024 (5)	0.0007 (5)
N5	0.0141 (5)	0.0152 (6)	0.0298 (7)	0.0049 (4)	0.0011 (5)	0.0014 (5)
O1	0.0179 (5)	0.0126 (5)	0.0307 (6)	−0.0002 (4)	0.0011 (4)	0.0052 (4)
O2	0.0174 (5)	0.0149 (5)	0.0202 (5)	0.0040 (4)	0.0030 (4)	0.0001 (4)
O3	0.0125 (4)	0.0164 (5)	0.0302 (6)	0.0040 (4)	0.0017 (4)	0.0010 (4)
S1	0.01264 (15)	0.01075 (15)	0.02213 (18)	0.00173 (11)	0.00165 (12)	0.00127 (12)

Geometric parameters (Å, º)

C2—N3	1.3266 (17)	C10—C13	1.512 (2)
C2—N2	1.3344 (17)	C11—C12	1.394 (2)
C2—N1	1.3637 (17)	C11—H11	0.9500
C4—N4	1.3325 (17)	C12—H12	0.9500
C4—N3	1.3638 (17)	C13—H13A	0.9800
C4—C5	1.4091 (18)	C13—H13B	0.9800
C5—C6	1.3739 (19)	C13—H13C	0.9800
C5—H5	0.9500	N1—H1	0.90 (2)
C6—N5	1.3460 (18)	N2—H2A	0.87 (2)
C6—N1	1.3675 (17)	N2—H2B	0.89 (2)
C7—C8	1.387 (2)	N4—H4A	0.87 (2)
C7—C12	1.392 (2)	N4—H4B	0.85 (2)
C7—S1	1.7664 (15)	N5—H5A	0.88 (2)
C8—C9	1.393 (2)	N5—H5B	0.84 (2)
C8—H8	0.9500	O1—S1	1.4646 (11)
C9—C10	1.394 (2)	O2—S1	1.4604 (12)
C9—H9	0.9500	O3—S1	1.4664 (11)
C10—C11	1.388 (2)
N3—C2—N2	120.33 (13)	C7—C12—H12	120.4
N3—C2—N1	122.80 (12)	C11—C12—H12	120.4
N2—C2—N1	116.87 (12)	C10—C13—H13A	109.5
N4—C4—N3	115.92 (12)	C10—C13—H13B	109.5
N4—C4—C5	121.38 (13)	H13A—C13—H13B	109.5
N3—C4—C5	122.68 (12)	C10—C13—H13C	109.5
C6—C5—C4	117.95 (12)	H13A—C13—H13C	109.5
C6—C5—H5	121.0	H13B—C13—H13C	109.5
C4—C5—H5	121.0	C2—N1—C6	121.16 (12)
N5—C6—N1	116.06 (12)	C2—N1—H1	119.4 (15)
N5—C6—C5	125.53 (13)	C6—N1—H1	119.4 (15)
N1—C6—C5	118.40 (12)	C2—N2—H2A	117.6 (14)
C8—C7—C12	120.21 (14)	C2—N2—H2B	118.8 (14)
C8—C7—S1	119.42 (11)	H2A—N2—H2B	123 (2)
C12—C7—S1	120.37 (12)	C2—N3—C4	116.99 (12)
C7—C8—C9	119.71 (15)	C4—N4—H4A	121.2 (15)
C7—C8—H8	120.1	C4—N4—H4B	120.3 (14)
C9—C8—H8	120.1	H4A—N4—H4B	119 (2)
C8—C9—C10	121.00 (16)	C6—N5—H5A	120.8 (15)
C8—C9—H9	119.5	C6—N5—H5B	118.2 (14)
C10—C9—H9	119.5	H5A—N5—H5B	118 (2)
C11—C10—C9	118.31 (14)	O2—S1—O1	112.39 (7)
C11—C10—C13	120.40 (14)	O2—S1—O3	112.56 (7)
C9—C10—C13	121.29 (15)	O1—S1—O3	111.55 (6)
C10—C11—C12	121.48 (14)	O2—S1—C7	106.99 (7)
C10—C11—H11	119.3	O1—S1—C7	106.39 (7)
C12—C11—H11	119.3	O3—S1—C7	106.46 (7)
C7—C12—C11	119.21 (14)
N4—C4—C5—C6	−176.96 (14)	N3—C2—N1—C6	1.2 (2)
N3—C4—C5—C6	1.6 (2)	N2—C2—N1—C6	−179.04 (13)
C4—C5—C6—N5	−179.59 (14)	N5—C6—N1—C2	178.40 (14)
C4—C5—C6—N1	−0.6 (2)	C5—C6—N1—C2	−0.7 (2)
C12—C7—C8—C9	−1.9 (3)	N2—C2—N3—C4	179.96 (13)
S1—C7—C8—C9	179.22 (14)	N1—C2—N3—C4	−0.3 (2)
C7—C8—C9—C10	−0.5 (3)	N4—C4—N3—C2	177.48 (14)
C8—C9—C10—C11	2.7 (3)	C5—C4—N3—C2	−1.1 (2)
C8—C9—C10—C13	−177.88 (17)	C8—C7—S1—O2	−157.57 (13)
C9—C10—C11—C12	−2.5 (3)	C12—C7—S1—O2	23.55 (14)
C13—C10—C11—C12	178.10 (15)	C8—C7—S1—O1	82.09 (14)
C8—C7—C12—C11	2.1 (2)	C12—C7—S1—O1	−96.80 (13)
S1—C7—C12—C11	−179.01 (12)	C8—C7—S1—O3	−37.01 (15)
C10—C11—C12—C7	0.1 (3)	C12—C7—S1—O3	144.11 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1	0.90 (2)	2.87 (2)	3.7230 (12)	159.8 (19)
N1—H1···O1	0.90 (2)	1.83 (2)	2.7234 (16)	174 (2)
N2—H2A···O2^i	0.87 (2)	2.05 (2)	2.8685 (16)	156 (2)
N2—H2B···S1	0.89 (2)	2.96 (2)	3.7966 (13)	157.7 (18)
N2—H2B···O3	0.89 (2)	2.06 (2)	2.9437 (17)	174 (2)
N4—H4A···N3^ii	0.87 (2)	2.17 (2)	3.0435 (17)	178 (2)
N4—H4B···O2^iii	0.85 (2)	2.18 (2)	2.9410 (17)	148.9 (19)
N5—H5B···O3^iv	0.84 (2)	2.13 (2)	2.9698 (17)	175 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x+3, −y+2, −z+2; (iii) x+1, y+1, z; (iv) x, y+1, z.