4-Amino-3,5-dimethyl-4H-1,2,4-triazole.

In the title compound, C(4)H(8)N(4), inter-molecular N-H⋯N hydrogen bonds involving the amino groups and triazole N atoms form a two-dimensional sheet.

Related literature

For background, see: Desenko (1995 ▶); For further synthetic details, see: Van Albada et al. (1984 ▶). For related literature, see: Allen et al. (1987 ▶); Ding et al. (2004 ▶); Steel (2005 ▶); Van Diemen et al. (1991 ▶); Yi et al. (2004 ▶).

Experimental

Crystal data

C4H8N4

M = 112.14

Monoclinic,

a = 5.8423 (12) Å

b = 7.7540 (16) Å

c = 12.846 (3) Å

β = 96.91 (3)°

V = 577.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: none

5941 measured reflections

1333 independent reflections

1101 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.142

S = 1.12

1333 reflections

81 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014815/bv2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014815/bv2093Isup2.hkl

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

C4H8N4	F000 = 240
Mr = 112.14	Dx = 1.289 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5363 reflections
a = 5.8423 (12) Å	θ = 3.1–27.5º
b = 7.7540 (16) Å	µ = 0.09 mm−1
c = 12.846 (3) Å	T = 293 (2) K
β = 96.91 (3)º	Block, colourless
V = 577.7 (2) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	1101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Monochromator: graphite	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −7→7
Absorption correction: none	k = −10→10
5941 measured reflections	l = −16→16
1333 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.068P)2 + 0.1583P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
1333 reflections	Δρmax = 0.20 e Å−3
81 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N3	1.0528 (2)	0.17414 (16)	0.13102 (10)	0.0297 (3)
N4	1.2366 (2)	0.2703 (2)	0.09833 (12)	0.0396 (4)
N2	0.8357 (3)	0.02909 (19)	0.22608 (11)	0.0408 (4)
N1	0.7072 (2)	0.06903 (19)	0.13019 (12)	0.0406 (4)
C2	0.8418 (3)	0.1557 (2)	0.07503 (12)	0.0322 (4)
C1	1.0418 (3)	0.0933 (2)	0.22443 (13)	0.0323 (4)
C3	1.2408 (3)	0.0804 (3)	0.30796 (15)	0.0481 (5)
H3A	1.1950	0.0182	0.3667	0.072*
H3B	1.2906	0.1941	0.3299	0.072*
H3C	1.3651	0.0206	0.2812	0.072*
C4	0.7788 (3)	0.2255 (3)	−0.03203 (14)	0.0467 (5)
H4A	0.6213	0.1969	−0.0559	0.070*
H4B	0.8775	0.1762	−0.0787	0.070*
H4C	0.7968	0.3486	−0.0308	0.070*
H4D	1.362 (4)	0.200 (3)	0.1041 (18)	0.060 (6)*
H4E	1.263 (4)	0.361 (3)	0.1488 (19)	0.064 (7)*

	U11	U22	U33	U12	U13	U23
N3	0.0243 (7)	0.0317 (7)	0.0332 (7)	−0.0002 (5)	0.0036 (5)	−0.0007 (5)
N4	0.0288 (8)	0.0462 (9)	0.0446 (9)	−0.0059 (7)	0.0082 (6)	0.0035 (7)
N2	0.0359 (8)	0.0444 (8)	0.0421 (9)	−0.0032 (6)	0.0042 (6)	0.0060 (6)
N1	0.0296 (7)	0.0453 (8)	0.0458 (9)	−0.0045 (6)	0.0003 (6)	0.0014 (7)
C2	0.0272 (8)	0.0332 (8)	0.0353 (8)	0.0019 (6)	0.0006 (6)	−0.0042 (6)
C1	0.0301 (8)	0.0323 (8)	0.0342 (9)	0.0017 (6)	0.0029 (6)	0.0009 (6)
C3	0.0413 (10)	0.0579 (11)	0.0426 (10)	0.0024 (9)	−0.0060 (8)	0.0093 (9)
C4	0.0457 (11)	0.0541 (11)	0.0378 (10)	0.0022 (9)	−0.0050 (8)	0.0020 (8)

N3—C2	1.358 (2)	C2—C4	1.482 (2)
N3—C1	1.362 (2)	C1—C3	1.487 (2)
N3—N4	1.4123 (18)	C3—H3A	0.9600
N4—H4D	0.91 (2)	C3—H3B	0.9600
N4—H4E	0.95 (2)	C3—H3C	0.9600
N2—C1	1.305 (2)	C4—H4A	0.9600
N2—N1	1.398 (2)	C4—H4B	0.9600
N1—C2	1.306 (2)	C4—H4C	0.9600
C2—N3—C1	106.40 (13)	N3—C1—C3	123.42 (15)
C2—N3—N4	124.91 (14)	C1—C3—H3A	109.5
C1—N3—N4	128.54 (13)	C1—C3—H3B	109.5
N3—N4—H4D	106.9 (14)	H3A—C3—H3B	109.5
N3—N4—H4E	104.6 (13)	C1—C3—H3C	109.5
H4D—N4—H4E	109 (2)	H3A—C3—H3C	109.5
C1—N2—N1	107.45 (14)	H3B—C3—H3C	109.5
C2—N1—N2	107.31 (13)	C2—C4—H4A	109.5
N1—C2—N3	109.51 (14)	C2—C4—H4B	109.5
N1—C2—C4	126.35 (15)	H4A—C4—H4B	109.5
N3—C2—C4	124.14 (15)	C2—C4—H4C	109.5
N2—C1—N3	109.34 (14)	H4A—C4—H4C	109.5
N2—C1—C3	127.23 (16)	H4B—C4—H4C	109.5
C1—N2—N1—C2	−0.04 (18)	N1—N2—C1—N3	0.12 (18)
N2—N1—C2—N3	−0.05 (18)	N1—N2—C1—C3	−178.51 (17)
N2—N1—C2—C4	−179.82 (16)	C2—N3—C1—N2	−0.15 (18)
C1—N3—C2—N1	0.12 (18)	N4—N3—C1—N2	175.53 (15)
N4—N3—C2—N1	−175.76 (14)	C2—N3—C1—C3	178.54 (16)
C1—N3—C2—C4	179.90 (15)	N4—N3—C1—C3	−5.8 (3)
N4—N3—C2—C4	4.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4D···N1i	0.91 (2)	2.25 (2)	3.145 (2)	170 (2)
N)—H4E···N2ii	0.96 (2)	2.20 (2)	3.086 (2)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4D⋯N1i	0.91 (2)	2.25 (2)	3.145 (2)	170 (2)
N)—H4E⋯N2ii	0.96 (2)	2.20 (2)	3.086 (2)	154 (2)

Symmetry codes: (i) ; (ii) .