3-Amino-5,6-dimethyl-1,2,4-triazin-2-ium nitrate.

In the title compound, C5H9N4 (+)·NO3 (-), the organic cations and the nitrate anions have both crystallographically imposed mirror symmetry and are linked via N-H⋯O hydrogen bonds, forming infinite chains running along the c-axis direction. The values of the N-O bond lengths [1.2256 (19)-1.2642 (18) Å] and O-N-O angles [118.39 (16)-121.64 (15)°] indicate that the nitrate anion exhibits a slightly distorted C3h geometry. The N atom of the NH2 group has sp (2) character.

Related literature

For general background to hybrid materials, see: Benali-Cherif et al. (2007 ▶); Messai et al. (2009 ▶). For studies of amine salts, see: Jayaraman et al. (2002 ▶); Steiner (2002 ▶). For related structures, see: Gilli et al. (1994 ▶); Boenigk & Mootz (1988 ▶); Jin et al. (2001 ▶).

Experimental

Crystal data

C5H9N4 +·NO3 −

M = 187.17

Orthorhombic,

a = 19.7213 (2) Å

b = 6.4245 (2) Å

c = 6.7197 (6) Å

V = 851.38 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.32 × 0.18 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

2321 measured reflections

1326 independent reflections

1031 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.161

S = 1.04

1326 reflections

102 parameters

All H-atom parameters refined

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1997 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012026/rz5062sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012026/rz5062Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012026/rz5062Isup3.cml

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

C5H9N4+·NO3−	F(000) = 392
Mr = 187.17	Dx = 1.460 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2321 reflections
a = 19.7213 (2) Å	θ = 2.0–30.0°
b = 6.4245 (2) Å	µ = 0.12 mm−1
c = 6.7197 (6) Å	T = 295 K
V = 851.38 (8) Å3	Rod, colourless
Z = 4	0.32 × 0.18 × 0.12 mm

Nonius KappaCCD diffractometer	1031 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 30.0°, θmin = 3.8°
φ scans and ω scans	h = −27→27
2321 measured reflections	k = −8→8
1326 independent reflections	l = −9→9

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)] = 0.049	Hydrogen site location: difference Fourier map
wR(F2) = 0.161	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.1038P)2 + 0.061P] where P = (Fo2 + 2Fc2)/3
1326 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 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
O1	−0.07155 (6)	0.2500	−0.1964 (2)	0.0634 (4)
O2	−0.15520 (7)	0.2500	0.0121 (2)	0.0705 (5)
O3	−0.17374 (7)	0.2500	−0.3030 (2)	0.0767 (5)
N1	0.04674 (7)	0.2500	0.4549 (2)	0.0477 (4)
N2	0.08600 (8)	0.2500	0.0580 (2)	0.0520 (4)
N3	0.02034 (7)	0.2500	0.11531 (19)	0.0478 (4)
N4	−0.06438 (7)	0.2500	0.3511 (2)	0.0562 (4)
N5	−0.13454 (7)	0.2500	−0.1615 (2)	0.0519 (4)
C1	0.00063 (7)	0.2500	0.3055 (2)	0.0419 (4)
C2	0.13126 (8)	0.2500	0.1986 (2)	0.0479 (4)
C3	0.11066 (8)	0.2500	0.4046 (2)	0.0462 (4)
C4	0.20428 (9)	0.2500	0.1392 (4)	0.0650 (5)
C5	0.16177 (11)	0.2500	0.5668 (3)	0.0695 (6)
H1N	−0.1005 (17)	0.2500	0.254 (5)	0.100 (9)*
H2N	−0.0701 (14)	0.2500	0.479 (5)	0.083 (8)*
H3N	−0.0130 (17)	0.2500	0.007 (5)	0.086 (7)*
H1	0.2269 (9)	0.133 (3)	0.203 (3)	0.092 (6)*
H2	0.206 (3)	0.2500	0.019 (9)	0.153 (16)*
H3	0.1438 (16)	0.2500	0.683 (5)	0.102 (10)*
H4	0.1920 (13)	0.130 (3)	0.544 (4)	0.128 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0410 (6)	0.1020 (10)	0.0472 (7)	0.000	0.0003 (5)	0.000
O2	0.0505 (7)	0.1173 (12)	0.0438 (7)	0.000	0.0051 (6)	0.000
O3	0.0532 (8)	0.1263 (14)	0.0506 (8)	0.000	−0.0160 (6)	0.000
N1	0.0417 (7)	0.0647 (8)	0.0366 (6)	0.000	−0.0006 (5)	0.000
N2	0.0452 (7)	0.0729 (9)	0.0379 (7)	0.000	0.0026 (5)	0.000
N3	0.0419 (7)	0.0646 (8)	0.0369 (6)	0.000	−0.0028 (5)	0.000
N4	0.0405 (7)	0.0801 (10)	0.0480 (8)	0.000	0.0019 (6)	0.000
N5	0.0421 (7)	0.0695 (9)	0.0441 (7)	0.000	−0.0033 (5)	0.000
C1	0.0400 (7)	0.0475 (7)	0.0381 (7)	0.000	−0.0010 (6)	0.000
C2	0.0421 (7)	0.0592 (9)	0.0424 (8)	0.000	0.0024 (6)	0.000
C3	0.0412 (7)	0.0583 (8)	0.0390 (7)	0.000	−0.0015 (6)	0.000
C4	0.0416 (8)	0.0970 (15)	0.0564 (11)	0.000	0.0075 (8)	0.000
C5	0.0474 (9)	0.1150 (18)	0.0461 (10)	0.000	−0.0072 (8)	0.000

O1—N5	1.2642 (18)	N4—H1N	0.97 (3)
O2—N5	1.236 (2)	N4—H2N	0.87 (4)
O3—N5	1.2256 (19)	C2—C3	1.443 (2)
N1—C3	1.305 (2)	C2—C4	1.494 (2)
N1—C1	1.3547 (19)	C3—C5	1.485 (2)
N2—C2	1.300 (2)	C4—H1	0.972 (17)
N2—N3	1.3510 (19)	C4—H2	0.81 (6)
N3—C1	1.3357 (19)	C5—H3	0.86 (3)
N3—H3N	0.98 (4)	C5—H4	0.99 (2)
N4—C1	1.3183 (19)
C3—N1—C1	117.14 (14)	N3—C1—N1	120.93 (14)
C2—N2—N3	116.81 (14)	N2—C2—C3	120.27 (15)
C1—N3—N2	123.48 (13)	N2—C2—C4	117.90 (16)
C1—N3—H3N	121 (2)	C3—C2—C4	121.83 (15)
N2—N3—H3N	116 (2)	N1—C3—C2	121.37 (14)
C1—N4—H1N	124 (2)	N1—C3—C5	117.75 (16)
C1—N4—H2N	111.0 (18)	C2—C3—C5	120.88 (15)
H1N—N4—H2N	125 (2)	C2—C4—H1	108.9 (11)
O3—N5—O2	121.64 (15)	C2—C4—H2	108 (4)
O3—N5—O1	118.39 (16)	H1—C4—H2	115 (2)
O2—N5—O1	119.97 (15)	C3—C5—H3	113 (2)
N4—C1—N3	120.37 (14)	C3—C5—H4	107.1 (15)
N4—C1—N1	118.70 (15)	H3—C5—H4	113.1 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.98 (4)	1.79 (4)	2.770 (2)	178 (3)
N4—H1N···O2	0.97 (3)	1.93 (3)	2.898 (2)	166 (3)
N4—H2N···O1i	0.87 (4)	2.18 (4)	3.043 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1	0.98 (4)	1.79 (4)	2.770 (2)	178 (3)
N4—H1N⋯O2	0.97 (3)	1.93 (3)	2.898 (2)	166 (3)
N4—H2N⋯O1i	0.87 (4)	2.18 (4)	3.043 (2)	173 (3)

Symmetry code: (i) .