2-Amino-4,6-dimethyl-pyrimidinium dihydrogenphosphate.

In the crystal structure of the title compound, C(6)H(10)N(3) (+)·H(2)PO(4) (-), the cations and anions are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming a two-dimensional network. Additional stabilization is provided by weak inter-molecular C-H⋯O inter-actions. N-H⋯N inter-actions are also present.

Related literature

Five and six-membered heterocyclic compounds often exist in biologically active natural products and synthetic compounds of medicinal inter­est, see: Gilchrist (1998 ▶). For methyl­pyrimidines as precursors to potentially bioactive pyrimidine derivatives, see: Xue et al. (1993 ▶). For Ru complexes of pyrim­idine with an –NH2 substituent, see: Zhu et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H10N3 +·H2PO4 −

M = 221.16

Monoclinic,

a = 11.743 (2) Å

b = 4.8266 (10) Å

c = 16.940 (3) Å

β = 95.55 (3)°

V = 955.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.20 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8743 measured reflections

2193 independent reflections

1973 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.108

S = 1.08

2193 reflections

133 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903880X/lh2909sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903880X/lh2909Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H10N3+·H2PO4−	F(000) = 464
Mr = 221.16	Dx = 1.537 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1973 reflections
a = 11.743 (2) Å	θ = 3.5–27.5°
b = 4.8266 (10) Å	µ = 0.28 mm−1
c = 16.940 (3) Å	T = 293 K
β = 95.55 (3)°	Block, colorless
V = 955.6 (3) Å3	0.20 × 0.15 × 0.11 mm
Z = 4

Bruker SMART CCD diffractometer	1973 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 27.5°, θmin = 3.5°
φ and ω scans	h = −15→15
8743 measured reflections	k = −6→5
2193 independent reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.3094P] where P = (Fo2 + 2Fc2)/3
2193 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
P1	0.09666 (3)	0.22149 (8)	0.74781 (2)	0.02327 (14)
O1	0.17203 (9)	0.3129 (2)	0.82063 (6)	0.0302 (3)
O2	0.01084 (9)	0.4557 (2)	0.71860 (7)	0.0337 (3)
H2A	0.0243	0.6265	0.7326	0.085 (9)*
O3	0.02931 (10)	−0.0362 (2)	0.76133 (7)	0.0339 (3)
N1	0.20023 (11)	0.0034 (3)	0.95145 (7)	0.0270 (3)
H1A	0.1936	0.0900	0.9021	0.052 (6)*
O4	0.16964 (11)	0.1887 (3)	0.67571 (7)	0.0381 (3)
H4A	0.2241	0.0508	0.6822	0.084 (9)*
N3	0.02982 (11)	−0.2279 (3)	0.91928 (8)	0.0322 (3)
H3B	−0.0198	−0.3692	0.9308	0.032 (4)*
H3A	0.0243	−0.1573	0.8748	0.044 (6)*
C1	0.12099 (12)	−0.1846 (3)	0.96966 (8)	0.0252 (3)
N2	0.13194 (11)	−0.3247 (3)	1.03924 (7)	0.0282 (3)
C4	0.29458 (13)	0.0550 (3)	1.00208 (9)	0.0300 (3)
C2	0.22244 (14)	−0.2691 (3)	1.09017 (9)	0.0294 (3)
C3	0.30667 (13)	−0.0793 (4)	1.07340 (9)	0.0341 (3)
H3D	0.3695	−0.0453	1.1099	0.041*
C6	0.37991 (16)	0.2522 (4)	0.97449 (12)	0.0417 (4)
H6A	0.3427	0.4240	0.9594	0.063*
H6B	0.4128	0.1748	0.9297	0.063*
H6C	0.4391	0.2851	1.0166	0.063*
C5	0.23093 (16)	−0.4213 (4)	1.16774 (9)	0.0429 (4)
H5A	0.1664	−0.5429	1.1690	0.064*
H5B	0.2315	−0.2905	1.2105	0.064*
H5C	0.3002	−0.5280	1.1734	0.064*

	U11	U22	U33	U12	U13	U23
P1	0.0252 (2)	0.0188 (2)	0.0253 (2)	0.00191 (12)	−0.00052 (14)	0.00042 (12)
O1	0.0312 (6)	0.0308 (6)	0.0274 (5)	−0.0050 (4)	−0.0039 (4)	0.0044 (4)
O2	0.0333 (6)	0.0214 (5)	0.0437 (6)	0.0054 (4)	−0.0103 (4)	−0.0035 (4)
O3	0.0404 (6)	0.0207 (5)	0.0400 (6)	−0.0048 (4)	0.0005 (5)	0.0003 (4)
N1	0.0281 (6)	0.0277 (6)	0.0250 (6)	−0.0035 (5)	0.0012 (4)	0.0012 (5)
O4	0.0470 (7)	0.0380 (7)	0.0305 (6)	0.0135 (5)	0.0099 (5)	0.0051 (5)
N3	0.0327 (7)	0.0363 (7)	0.0263 (7)	−0.0087 (5)	−0.0031 (5)	0.0042 (5)
C1	0.0265 (7)	0.0256 (7)	0.0236 (7)	−0.0009 (5)	0.0026 (5)	−0.0008 (5)
N2	0.0303 (6)	0.0310 (7)	0.0233 (6)	−0.0038 (5)	0.0020 (5)	0.0020 (5)
C4	0.0277 (7)	0.0296 (7)	0.0322 (7)	−0.0034 (6)	0.0008 (5)	−0.0019 (6)
C2	0.0327 (8)	0.0313 (8)	0.0239 (7)	0.0003 (6)	0.0011 (5)	−0.0007 (5)
C3	0.0310 (8)	0.0391 (9)	0.0308 (7)	−0.0049 (7)	−0.0040 (6)	0.0005 (6)
C6	0.0346 (9)	0.0423 (10)	0.0475 (10)	−0.0125 (7)	−0.0002 (7)	0.0068 (7)
C5	0.0479 (10)	0.0532 (11)	0.0261 (7)	−0.0066 (8)	−0.0032 (6)	0.0089 (7)

P1—O3	1.5033 (12)	N2—C2	1.330 (2)
P1—O1	1.5128 (12)	C4—C3	1.366 (2)
P1—O2	1.5626 (11)	C4—C6	1.490 (2)
P1—O4	1.5665 (12)	C2—C3	1.397 (2)
O2—H2A	0.8679	C2—C5	1.500 (2)
N1—C1	1.3566 (19)	C3—H3D	0.9300
N1—C4	1.3568 (19)	C6—H6A	0.9600
N1—H1A	0.9317	C6—H6B	0.9600
O4—H4A	0.9225	C6—H6C	0.9600
N3—C1	1.3195 (19)	C5—H5A	0.9600
N3—H3B	0.9302	C5—H5B	0.9600
N3—H3A	0.8243	C5—H5C	0.9600
C1—N2	1.3542 (19)
O3—P1—O1	113.08 (6)	C3—C4—C6	124.41 (15)
O3—P1—O2	108.30 (7)	N2—C2—C3	122.50 (14)
O1—P1—O2	110.84 (7)	N2—C2—C5	116.78 (14)
O3—P1—O4	111.77 (7)	C3—C2—C5	120.72 (15)
O1—P1—O4	110.13 (7)	C4—C3—C2	118.42 (14)
O2—P1—O4	102.18 (7)	C4—C3—H3D	120.8
P1—O2—H2A	120.4	C2—C3—H3D	120.8
C1—N1—C4	121.00 (13)	C4—C6—H6A	109.5
C1—N1—H1A	120.3	C4—C6—H6B	109.5
C4—N1—H1A	118.5	H6A—C6—H6B	109.5
P1—O4—H4A	113.9	C4—C6—H6C	109.5
C1—N3—H3B	117.8	H6A—C6—H6C	109.5
C1—N3—H3A	120.9	H6B—C6—H6C	109.5
H3B—N3—H3A	119.9	C2—C5—H5A	109.5
N3—C1—N2	119.12 (14)	C2—C5—H5B	109.5
N3—C1—N1	119.36 (13)	H5A—C5—H5B	109.5
N2—C1—N1	121.51 (13)	C2—C5—H5C	109.5
C2—N2—C1	117.81 (13)	H5A—C5—H5C	109.5
N1—C4—C3	118.72 (14)	H5B—C5—H5C	109.5
N1—C4—C6	116.85 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.93	1.75	2.667 (2)	168
O2—H2A···O3i	0.87	1.70	2.560 (2)	171
N3—H3A···O3	0.82	2.02	2.831 (2)	170
N3—H3B···N2ii	0.93	2.07	3.004 (2)	178
O4—H4A···O1iii	0.92	1.68	2.594 (2)	171
C3—H3D···O2iv	0.93	2.40	3.319 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.93	1.75	2.667 (2)	168
O2—H2A⋯O3i	0.87	1.70	2.560 (2)	171
N3—H3A⋯O3	0.82	2.02	2.831 (2)	170
N3—H3B⋯N2ii	0.93	2.07	3.004 (2)	178
O4—H4A⋯O1iii	0.92	1.68	2.594 (2)	171
C3—H3D⋯O2iv	0.93	2.40	3.319 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .