2,4-Diamino-6-methyl-1,3,5-triazin-1-ium nitrate.

In the title salt, C(4)H(8)N(5) (+)·NO(3) (-), a ring N atom of 2,6-diamino-4-methyl-triazine is protonated. Each anion is connected to three neighbouring cations by multiple N-H⋯O hydrogen bonds which, together with N-H⋯N contacts, generate a layer structure.

Related literature

For 2,6-diamino-4-methyl­triazine compounds, see: Kaczmarek et al. (2008 ▶); Perpétuo & Janczak (2007 ▶); Portalone & Colapietro (2007 ▶); Wijaya et al. (2004 ▶); Xiao (2008 ▶).

Experimental

Crystal data

C4H8N5 +·n class="Chemical">NO3 −

M = 188.16

Monoclinic,

a = 7.667 (1) Å

b = 10.338 (2) Å

c = 9.977 (1) Å

β = 93.384 (2)°

V = 789.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 291 (2) K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

4763 measured reflections

1867 independent reflections

1202 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.178

S = 1.00

1867 reflections

138 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003900/ng2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003900/ng2537Isup2.hkl

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

C4H8N5+·NO3−	F(000) = 392
Mr = 188.16	Dx = 1.583 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1324 reflections
a = 7.667 (1) Å	θ = 2.8–26.0°
b = 10.338 (2) Å	µ = 0.14 mm−1
c = 9.977 (1) Å	T = 291 K
β = 93.384 (2)°	Block, colourless
V = 789.4 (2) Å3	0.13 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
graphite	θmax = 28.0°, θmin = 2.8°
φ and ω scans	h = −8→10
4763 measured reflections	k = −12→13
1867 independent reflections	l = −12→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.106P)2] where P = (Fo2 + 2Fc2)/3
1867 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.30 e Å−3
5 restraints	Δρmin = −0.38 e Å−3

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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
C1	0.0367 (3)	0.2000 (2)	0.8411 (2)	0.0350 (5)
C2	0.3207 (3)	0.2520 (2)	0.9243 (2)	0.0368 (5)
C3	0.2268 (3)	0.0451 (2)	0.9114 (2)	0.0340 (5)
C4	0.4496 (3)	0.3560 (2)	0.9556 (3)	0.0488 (6)
H4A	0.5589	0.3183	0.9872	0.073*
H4B	0.4074	0.4113	1.0239	0.073*
H4C	0.4661	0.4057	0.8761	0.073*
H2	0.129 (4)	0.372 (2)	0.858 (3)	0.067 (9)*
H4D	0.189 (3)	−0.137 (2)	0.909 (2)	0.034 (6)*
H4E	0.371 (4)	−0.096 (2)	0.965 (3)	0.044 (7)*
N1	0.0678 (2)	0.07622 (17)	0.85890 (19)	0.0366 (5)
N2	0.1626 (2)	0.29135 (19)	0.87137 (19)	0.0373 (5)
N3	0.3580 (2)	0.13121 (17)	0.94713 (19)	0.0358 (5)
N4	0.2668 (3)	−0.07814 (18)	0.9311 (2)	0.0415 (5)
N5	−0.1161 (3)	0.2428 (2)	0.7917 (2)	0.0484 (6)
H5A	−0.193 (3)	0.1810 (18)	0.771 (3)	0.082 (9)*
H5B	−0.131 (4)	0.3288 (11)	0.783 (3)	0.066 (9)*
N6	0.0038 (2)	0.61218 (18)	0.84158 (19)	0.0391 (5)
O1	−0.0186 (2)	0.73101 (16)	0.84536 (19)	0.0515 (5)
O2	0.1471 (2)	0.56484 (18)	0.8772 (2)	0.0582 (6)
O3	−0.1190 (3)	0.54094 (17)	0.7991 (2)	0.0596 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0308 (11)	0.0347 (12)	0.0391 (11)	0.0002 (8)	−0.0019 (8)	0.0011 (9)
C2	0.0326 (12)	0.0345 (12)	0.0426 (12)	−0.0011 (9)	−0.0030 (9)	−0.0022 (9)
C3	0.0316 (11)	0.0309 (11)	0.0394 (11)	−0.0013 (8)	0.0010 (9)	−0.0007 (8)
C4	0.0425 (14)	0.0299 (12)	0.0722 (16)	−0.0060 (9)	−0.0120 (12)	−0.0034 (11)
N1	0.0307 (10)	0.0306 (10)	0.0478 (11)	−0.0016 (7)	−0.0035 (8)	0.0007 (8)
N2	0.0337 (10)	0.0280 (10)	0.0493 (11)	0.0009 (7)	−0.0056 (8)	0.0022 (8)
N3	0.0315 (10)	0.0263 (9)	0.0488 (11)	−0.0008 (7)	−0.0054 (8)	−0.0018 (7)
N4	0.0322 (11)	0.0284 (11)	0.0629 (13)	−0.0031 (8)	−0.0070 (9)	0.0015 (8)
N5	0.0351 (11)	0.0422 (13)	0.0661 (13)	0.0015 (9)	−0.0122 (9)	0.0049 (10)
N6	0.0357 (11)	0.0339 (10)	0.0474 (11)	0.0038 (8)	−0.0007 (8)	0.0017 (8)
O1	0.0459 (10)	0.0359 (10)	0.0719 (12)	0.0047 (7)	−0.0045 (8)	−0.0026 (8)
O2	0.0414 (11)	0.0514 (12)	0.0796 (14)	0.0133 (8)	−0.0134 (9)	0.0030 (9)
O3	0.0468 (11)	0.0408 (10)	0.0896 (14)	−0.0073 (8)	−0.0107 (10)	−0.0001 (9)

C1—N1	1.311 (3)	C4—H4B	0.9600
C1—N5	1.321 (3)	C4—H4C	0.9600
C1—N2	1.371 (3)	N2—H2	0.88 (2)
C2—N3	1.298 (3)	N4—H4D	0.87 (2)
C2—N2	1.356 (3)	N4—H4E	0.87 (3)
C2—C4	1.481 (3)	N5—H5A	0.888 (10)
C3—N4	1.322 (3)	N5—H5B	0.900 (10)
C3—N1	1.337 (3)	N6—O2	1.236 (2)
C3—N3	1.375 (3)	N6—O1	1.241 (2)
C4—H4A	0.9600	N6—O3	1.249 (3)
N1—C1—N5	121.8 (2)	C1—N1—C3	116.22 (18)
N1—C1—N2	121.5 (2)	C2—N2—C1	118.7 (2)
N5—C1—N2	116.6 (2)	C2—N2—H2	126 (2)
N3—C2—N2	122.7 (2)	C1—N2—H2	115 (2)
N3—C2—C4	121.6 (2)	C2—N3—C3	115.26 (18)
N2—C2—C4	115.7 (2)	C3—N4—H4D	119.0 (17)
N4—C3—N1	119.2 (2)	C3—N4—H4E	117.7 (17)
N4—C3—N3	115.2 (2)	H4D—N4—H4E	123 (2)
N1—C3—N3	125.6 (2)	C1—N5—H5A	114.3 (16)
C2—C4—H4A	109.5	C1—N5—H5B	118 (2)
C2—C4—H4B	109.5	H5A—N5—H5B	128 (3)
H4A—C4—H4B	109.5	O2—N6—O1	120.34 (19)
C2—C4—H4C	109.5	O2—N6—O3	120.2 (2)
H4A—C4—H4C	109.5	O1—N6—O3	119.42 (18)
H4B—C4—H4C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.88 (2)	2.62 (2)	3.414 (3)	150 (3)
N2—H2···O2	0.88 (2)	2.00 (3)	2.831 (3)	156 (3)
N4—H4D···O1i	0.87 (2)	2.17 (2)	3.031 (3)	175 (2)
N4—H4E···N3ii	0.87 (3)	2.24 (3)	3.105 (3)	177 (2)
N5—H5B···O3	0.90 (1)	2.20 (1)	3.083 (3)	167 (3)
N5—H5A···O3iii	0.89 (1)	2.13 (1)	3.014 (3)	174 (3)
N5—H5A···O1iii	0.89 (1)	2.49 (2)	3.046 (3)	121 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.88 (2)	2.62 (2)	3.414 (3)	150 (3)
N2—H2⋯O2	0.88 (2)	2.00 (3)	2.831 (3)	156 (3)
N4—H4D⋯O1i	0.87 (2)	2.17 (2)	3.031 (3)	175 (2)
N4—H4E⋯N3ii	0.87 (3)	2.24 (3)	3.105 (3)	177 (2)
N5—H5B⋯O3	0.90 (1)	2.20 (1)	3.083 (3)	167 (3)
N5—H5A⋯O3iii	0.89 (1)	2.13 (1)	3.014 (3)	174 (3)
N5—H5A⋯O1iii	0.89 (1)	2.49 (2)	3.046 (3)	121 (2)

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