1-Isopropyl-ideneamino-1H-tetra-zol-5-amine.

The mol-ecule of the title compound, C(4)H(8)N(6), assumes an approximately planar structure, the methyl C atoms and the C atom to which they are bonded being out of the mean tetrazole ring plane by 0.108 and 0.139, and 0.144 Å, respectively. π-π stacking between parallel tetra-zole rings [centroid-centroid distance = 3.4663 (11) Å] is observed in the crystal structure. Inter-molecular N-H⋯N hydrogen bonding further helps to stabilize the crystal structure.

Related literature

For the preparation of the title compound, see: Gaponnik & Karavai (1984 ▶). For general background, see: Galvez-Ruiz et al. (2005 ▶); Joo et al. (2008 ▶). For a related structures, see: Lyakhov et al. (2005 ▶).

Experimental

Crystal data

C4H8N6

M = 140.16

Monoclinic,

a = 7.488 (2) Å

b = 7.4238 (19) Å

c = 11.997 (3) Å

β = 97.145 (3)°

V = 661.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 93 K

0.43 × 0.43 × 0.33 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: none

5172 measured reflections

1520 independent reflections

1334 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.088

S = 1.00

1520 reflections

101 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024994/xu2546sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024994/xu2546Isup2.hkl

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

C4H8N6	F(000) = 296
Mr = 140.16	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Melting point: 445 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.488 (2) Å	Cell parameters from 2076 reflections
b = 7.4238 (19) Å	θ = 3.1–27.5°
c = 11.997 (3) Å	µ = 0.10 mm−1
β = 97.145 (3)°	T = 93 K
V = 661.7 (3) Å3	Block, colourless
Z = 4	0.43 × 0.43 × 0.33 mm

Rigaku Saturn724+ diffractometer	1334 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.024
graphite	θmax = 27.5°, θmin = 3.2°
Detector resolution: 28.5714 pixels mm-1	h = −9→9
multi–scan	k = −8→9
5172 measured reflections	l = −15→15
1520 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.045P)2 + 0.16P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.28 e Å−3
1520 reflections	Δρmin = −0.17 e Å−3
101 parameters

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
N1	0.90734 (13)	0.19832 (13)	0.44509 (8)	0.0177 (2)
N2	0.84796 (13)	0.34792 (13)	0.38501 (8)	0.0182 (2)
N3	0.78344 (13)	0.46815 (13)	0.44617 (8)	0.0181 (2)
N4	0.79984 (12)	0.39605 (12)	0.55284 (7)	0.0144 (2)
N5	0.74880 (12)	0.46344 (12)	0.65193 (7)	0.0165 (2)
N6	0.91309 (15)	0.12338 (14)	0.63884 (8)	0.0223 (2)
C1	0.87689 (14)	0.23122 (15)	0.55029 (9)	0.0153 (2)
C2	0.66745 (14)	0.61599 (15)	0.65364 (9)	0.0169 (2)
C3	0.61800 (16)	0.74455 (16)	0.55860 (10)	0.0215 (3)
H3A	0.7275	0.7992	0.5366	0.026*
H3B	0.5397	0.8391	0.5825	0.026*
H3C	0.5545	0.6795	0.4945	0.026*
C4	0.62021 (16)	0.66948 (17)	0.76627 (10)	0.0232 (3)
H4A	0.6608	0.5760	0.8213	0.028*
H4B	0.4895	0.6838	0.7624	0.028*
H4C	0.6794	0.7837	0.7891	0.028*
H6A	0.887 (2)	0.156 (2)	0.7063 (14)	0.033 (4)*
H6B	0.972 (2)	0.025 (2)	0.6261 (13)	0.037 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0210 (5)	0.0176 (5)	0.0146 (5)	0.0012 (4)	0.0026 (4)	−0.0006 (4)
N2	0.0214 (5)	0.0174 (5)	0.0161 (5)	0.0008 (4)	0.0036 (4)	−0.0003 (4)
N3	0.0230 (5)	0.0186 (5)	0.0133 (4)	0.0000 (4)	0.0045 (4)	0.0006 (4)
N4	0.0175 (5)	0.0144 (5)	0.0117 (4)	0.0008 (3)	0.0030 (3)	−0.0010 (3)
N5	0.0192 (5)	0.0183 (5)	0.0127 (4)	−0.0001 (4)	0.0042 (4)	−0.0031 (4)
N6	0.0337 (6)	0.0202 (5)	0.0137 (5)	0.0093 (4)	0.0062 (4)	0.0008 (4)
C1	0.0152 (5)	0.0167 (5)	0.0141 (5)	−0.0007 (4)	0.0026 (4)	−0.0019 (4)
C2	0.0151 (5)	0.0167 (5)	0.0190 (6)	−0.0019 (4)	0.0025 (4)	−0.0029 (4)
C3	0.0243 (6)	0.0185 (6)	0.0220 (6)	0.0043 (4)	0.0045 (5)	0.0002 (5)
C4	0.0261 (6)	0.0244 (6)	0.0196 (6)	0.0046 (5)	0.0043 (5)	−0.0055 (5)

N1—C1	1.3326 (14)	N6—H6B	0.878 (17)
N1—N2	1.3678 (13)	C2—C4	1.4924 (16)
N2—N3	1.2870 (13)	C2—C3	1.4977 (16)
N3—N4	1.3784 (13)	C3—H3A	0.9800
N4—C1	1.3549 (14)	C3—H3B	0.9800
N4—N5	1.3866 (12)	C3—H3C	0.9800
N5—C2	1.2873 (15)	C4—H4A	0.9800
N6—C1	1.3309 (14)	C4—H4B	0.9800
N6—H6A	0.891 (17)	C4—H4C	0.9800
C1—N1—N2	105.52 (9)	N5—C2—C3	128.40 (10)
N3—N2—N1	112.53 (9)	C4—C2—C3	117.11 (10)
N2—N3—N4	105.28 (9)	C2—C3—H3A	109.5
C1—N4—N3	108.59 (9)	C2—C3—H3B	109.5
C1—N4—N5	120.58 (9)	H3A—C3—H3B	109.5
N3—N4—N5	130.82 (9)	C2—C3—H3C	109.5
C2—N5—N4	120.83 (9)	H3A—C3—H3C	109.5
C1—N6—H6A	121.1 (10)	H3B—C3—H3C	109.5
C1—N6—H6B	114.8 (10)	C2—C4—H4A	109.5
H6A—N6—H6B	123.9 (14)	C2—C4—H4B	109.5
N6—C1—N1	127.15 (11)	H4A—C4—H4B	109.5
N6—C1—N4	124.77 (10)	C2—C4—H4C	109.5
N1—C1—N4	108.08 (9)	H4A—C4—H4C	109.5
N5—C2—C4	114.48 (10)	H4B—C4—H4C	109.5
C1—N1—N2—N3	−0.23 (12)	N2—N1—C1—N4	0.45 (11)
N1—N2—N3—N4	−0.08 (12)	N3—N4—C1—N6	179.91 (10)
N2—N3—N4—C1	0.37 (11)	N5—N4—C1—N6	−1.31 (16)
N2—N3—N4—N5	−178.25 (10)	N3—N4—C1—N1	−0.52 (12)
C1—N4—N5—C2	−176.51 (10)	N5—N4—C1—N1	178.26 (9)
N3—N4—N5—C2	1.97 (17)	N4—N5—C2—C4	179.59 (9)
N2—N1—C1—N6	−179.99 (11)	N4—N5—C2—C3	−1.35 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N2i	0.890 (16)	2.200 (17)	3.0600 (16)	162.6 (13)
N6—H6B···N1ii	0.876 (15)	2.118 (15)	2.9770 (16)	166.4 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯N2i	0.890 (16)	2.200 (17)	3.0600 (16)	162.6 (13)
N6—H6B⋯N1ii	0.876 (15)	2.118 (15)	2.9770 (16)	166.4 (14)

Symmetry codes: (i) ; (ii) .