2-Amino-pyrimidinium nitrate.

In the title compound, C(4)H(6)N(3) (+)·NO(3) (-), the cation is coplanar with the anion (r.m.s. deviation = 0.048 Å), and links to the anion via an N-H⋯O hydrogen bond, forming an ion pair. In the crystal, adjacent ion pairs are further linked by N-H⋯O hydrogen bonds into linear chains running along the b axis.

Related literature

For the crystal structures of the 2-amino­pyrimidinium salts of other mineral acids, see: Czupiński et al. (2005 ▶); Lee et al. (2003 ▶); Ye et al. (2002 ▶).

Experimental

Crystal data

C4H6N3 +·NO3 −

M = 158.13

Monoclinic,

a = 12.632 (2) Å

b = 6.2160 (8) Å

c = 17.727 (2) Å

β = 99.009 (3)°

V = 1374.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.968, T max = 0.981

5139 measured reflections

1210 independent reflections

823 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.120

S = 0.99

1210 reflections

124 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052362/xu2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052362/xu2705Isup2.hkl

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

C4H6N3+·NO3−	F(000) = 656
Mr = 158.13	Dx = 1.528 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3773 reflections
a = 12.632 (2) Å	θ = 3.3–27.5°
b = 6.2160 (8) Å	µ = 0.13 mm−1
c = 17.727 (2) Å	T = 293 K
β = 99.009 (3)°	Prism, colorless
V = 1374.8 (3) Å3	0.25 × 0.20 × 0.15 mm
Z = 8

Rigaku R-AXIS RAPID IP diffractometer	1210 independent reflections
Radiation source: fine-focus sealed tube	823 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scan	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.968, Tmax = 0.981	k = −7→7
5139 measured reflections	l = −21→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
1210 reflections	(Δ/σ)max = 0.001
124 parameters	Δρmax = 0.19 e Å−3
6 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.61627 (16)	1.0844 (3)	0.47003 (8)	0.0892 (6)
O2	0.63012 (12)	1.3264 (2)	0.38605 (8)	0.0711 (5)
O3	0.61420 (14)	0.9926 (3)	0.35358 (9)	0.0797 (5)
N1	0.62478 (13)	0.3594 (3)	0.59174 (10)	0.0568 (5)
N2	0.62700 (13)	0.7155 (3)	0.63460 (9)	0.0575 (5)
N3	0.62544 (15)	0.6380 (3)	0.50731 (10)	0.0633 (5)
N4	0.62009 (13)	1.1341 (3)	0.40181 (9)	0.0560 (5)
C1	0.62639 (15)	0.5716 (3)	0.57800 (10)	0.0501 (5)
C2	0.62721 (17)	0.6376 (4)	0.70374 (12)	0.0616 (6)
C3	0.62702 (18)	0.4200 (4)	0.72104 (13)	0.0669 (6)
C4	0.62560 (17)	0.2810 (4)	0.66282 (13)	0.0638 (6)
H1	0.6222 (17)	0.268 (3)	0.5539 (10)	0.074 (7)*
H11	0.6213 (19)	0.7733 (19)	0.4964 (16)	0.083 (8)*
H12	0.6282 (16)	0.547 (3)	0.4718 (9)	0.068 (7)*
H2	0.6222 (18)	0.749 (3)	0.7401 (13)	0.079 (7)*
H3	0.628 (2)	0.378 (4)	0.7724 (10)	0.087 (7)*
H4	0.6234 (17)	0.130 (3)	0.6655 (12)	0.068 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.1669 (17)	0.0547 (10)	0.0505 (9)	0.0094 (10)	0.0311 (9)	0.0031 (7)
O2	0.1061 (12)	0.0523 (10)	0.0576 (9)	−0.0043 (8)	0.0217 (8)	0.0025 (7)
O3	0.1178 (13)	0.0620 (11)	0.0620 (9)	−0.0010 (9)	0.0227 (8)	−0.0182 (8)
N1	0.0695 (11)	0.0435 (11)	0.0575 (10)	0.0026 (7)	0.0104 (8)	−0.0033 (8)
N2	0.0713 (11)	0.0478 (10)	0.0543 (9)	0.0030 (8)	0.0126 (8)	−0.0039 (8)
N3	0.0928 (13)	0.0486 (13)	0.0504 (10)	0.0032 (9)	0.0174 (9)	−0.0014 (8)
N4	0.0677 (10)	0.0512 (11)	0.0506 (10)	0.0046 (8)	0.0144 (8)	−0.0020 (8)
C1	0.0535 (11)	0.0447 (12)	0.0520 (10)	0.0022 (8)	0.0077 (8)	−0.0022 (8)
C2	0.0742 (14)	0.0584 (15)	0.0533 (12)	0.0030 (10)	0.0131 (10)	−0.0047 (10)
C3	0.0787 (15)	0.0674 (15)	0.0559 (12)	0.0022 (11)	0.0146 (11)	0.0062 (12)
C4	0.0736 (14)	0.0500 (14)	0.0676 (13)	0.0011 (10)	0.0104 (11)	0.0089 (11)

O1—N4	1.257 (2)	N3—C1	1.318 (3)
O2—N4	1.239 (2)	N3—H11	0.86 (1)
O3—N4	1.221 (2)	N3—H12	0.85 (1)
N1—C1	1.342 (2)	C2—C3	1.387 (3)
N1—C4	1.350 (3)	C2—H2	0.953 (16)
N1—H1	0.87 (1)	C3—C4	1.344 (3)
N2—C2	1.318 (3)	C3—H3	0.944 (17)
N2—C1	1.344 (2)	C4—H4	0.942 (16)
C1—N1—C4	121.76 (19)	N3—C1—N2	119.96 (19)
C1—N1—H1	119.8 (16)	N1—C1—N2	121.17 (18)
C4—N1—H1	118.4 (17)	N2—C2—C3	124.4 (2)
C2—N2—C1	116.65 (18)	N2—C2—H2	111.8 (15)
C1—N3—H11	120.6 (19)	C3—C2—H2	123.6 (15)
C1—N3—H12	120.0 (16)	C4—C3—C2	117.2 (2)
H11—N3—H12	119 (3)	C4—C3—H3	123.9 (16)
O3—N4—O2	122.31 (17)	C2—C3—H3	118.9 (15)
O3—N4—O1	119.30 (18)	C3—C4—N1	118.8 (2)
O2—N4—O1	118.39 (16)	C3—C4—H4	126.9 (13)
N3—C1—N1	118.86 (18)	N1—C4—H4	114.3 (13)
C4—N1—C1—N3	−179.98 (18)	C1—N2—C2—C3	0.1 (3)
C4—N1—C1—N2	−1.2 (3)	N2—C2—C3—C4	−0.6 (3)
C2—N2—C1—N3	179.55 (19)	C2—C3—C4—N1	0.2 (3)
C2—N2—C1—N1	0.8 (3)	C1—N1—C4—C3	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (1)	1.87 (1)	2.742 (2)	177 (2)
N3—H11···O1	0.86 (1)	1.99 (1)	2.850 (3)	178 (2)
N3—H12···O2i	0.85 (1)	2.05 (1)	2.901 (2)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (1)	1.87 (1)	2.742 (2)	177 (2)
N3—H11⋯O1	0.86 (1)	1.99 (1)	2.850 (3)	178 (2)
N3—H12⋯O2i	0.85 (1)	2.05 (1)	2.901 (2)	178 (2)

Symmetry code: (i) .