(5Z,7Z)-6,8-Dimethyl-9H-tetra-zolo[1,5-b][1,2,4]triazepine.

The mol-ecule of the title compound, C(6)H(8)N(6), is approximately planar, with a maximum deviation from planarity of 0.099 (1) Å. In the crystal, mol-ecules are linked to each other via pairs of N-H⋯N hydrogen bonding, forming inversion dimers. The crystal structure is further stabilized by π-π stacking inter-actions, with a centroid-centroid distance of 3.419 (1) Å.

Related literature

For the preparation of the title compound, see: Gaponnik & Karavai (1984 ▶). For applications of fused tetra­zole ring compounds, see: Taha 2007 ▶; Zbigniew et al. (2007 ▶); Galvez-Ruiz et al. (2005 ▶); Klapötke & Sabaté (2008 ▶). For related structures, see: Taha (2005 ▶); He et al. (2009a ▶,b ▶).

Experimental

Crystal data

C6H8N6

M = 164.18

Monoclinic,

a = 3.9184 (8) Å

b = 13.584 (3) Å

c = 13.767 (3) Å

β = 96.274 (3)°

V = 728.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 93 K

0.47 × 0.33 × 0.13 mm

Data collection

Rigaku Saturn 724+ diffractometer

Absorption correction: none

5029 measured reflections

1647 independent reflections

1445 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.082

S = 1.00

1647 reflections

119 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.22 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 I, global. DOI: 10.1107/S160053680904392X/wn2354sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904392X/wn2354Isup2.hkl

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

C6H8N6	F(000) = 344
Mr = 164.18	Dx = 1.497 Mg m−3
Monoclinic, P21/c	Melting point: 477 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 3.9184 (8) Å	Cell parameters from 2263 reflections
b = 13.584 (3) Å	θ = 3.3–27.5°
c = 13.767 (3) Å	µ = 0.11 mm−1
β = 96.274 (3)°	T = 93 K
V = 728.4 (3) Å3	Chunk, red
Z = 4	0.47 × 0.33 × 0.13 mm

Rigaku Saturn 724+ diffractometer	1445 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.019
graphite	θmax = 27.5°, θmin = 3.3°
Detector resolution: 28.5714 pixels mm-1	h = −4→5
multi–scan	k = −17→17
5029 measured reflections	l = −11→17
1647 independent reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.031P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3
1647 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.4467 (3)	0.24707 (7)	0.45448 (7)	0.0165 (2)
N2	0.5870 (3)	0.24983 (8)	0.36816 (7)	0.0208 (2)
N3	0.6547 (3)	0.16030 (8)	0.34635 (8)	0.0223 (3)
N4	0.5650 (3)	0.09674 (8)	0.41698 (7)	0.0195 (2)
N5	0.3238 (3)	0.11503 (8)	0.56546 (8)	0.0207 (3)
N6	0.3868 (3)	0.34046 (7)	0.49433 (7)	0.0176 (2)
C1	0.4389 (3)	0.15238 (9)	0.48318 (8)	0.0163 (3)
C2	0.1660 (3)	0.16746 (9)	0.63408 (8)	0.0165 (3)
C3	0.1175 (3)	0.26544 (9)	0.63462 (9)	0.0180 (3)
C4	0.2395 (3)	0.34313 (9)	0.57359 (9)	0.0165 (3)
C5	0.0598 (3)	0.10241 (9)	0.71313 (9)	0.0202 (3)
H5A	0.2595	0.0819	0.7548	0.024*
H5B	−0.0569	0.0456	0.6844	0.024*
H5C	−0.0914	0.1380	0.7509	0.024*
C6	0.1945 (3)	0.44529 (9)	0.61191 (9)	0.0206 (3)
H6A	0.2920	0.4920	0.5705	0.025*
H6B	0.3084	0.4503	0.6771	0.025*
H6C	−0.0457	0.4588	0.6126	0.025*
H3	0.006 (4)	0.2905 (11)	0.6876 (11)	0.025 (4)*
H5N	0.342 (4)	0.0478 (14)	0.5724 (12)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0214 (5)	0.0138 (5)	0.0148 (5)	0.0006 (4)	0.0043 (4)	0.0002 (4)
N2	0.0285 (6)	0.0182 (5)	0.0167 (5)	0.0010 (4)	0.0074 (4)	0.0004 (4)
N3	0.0309 (6)	0.0180 (5)	0.0191 (5)	0.0013 (5)	0.0078 (4)	0.0014 (4)
N4	0.0261 (6)	0.0167 (5)	0.0166 (5)	0.0007 (4)	0.0062 (4)	0.0005 (4)
N5	0.0315 (6)	0.0130 (5)	0.0193 (5)	0.0016 (4)	0.0106 (5)	0.0019 (4)
N6	0.0230 (5)	0.0110 (5)	0.0189 (5)	0.0009 (4)	0.0030 (4)	−0.0018 (4)
C1	0.0177 (6)	0.0151 (6)	0.0161 (6)	0.0000 (5)	0.0013 (4)	0.0005 (4)
C2	0.0174 (6)	0.0168 (6)	0.0153 (5)	−0.0009 (5)	0.0021 (4)	−0.0007 (4)
C3	0.0196 (6)	0.0181 (6)	0.0168 (6)	0.0000 (5)	0.0050 (5)	−0.0007 (5)
C4	0.0163 (6)	0.0147 (6)	0.0181 (6)	0.0004 (4)	−0.0002 (5)	−0.0002 (4)
C5	0.0240 (6)	0.0174 (6)	0.0202 (6)	−0.0003 (5)	0.0072 (5)	0.0024 (5)
C6	0.0246 (6)	0.0155 (6)	0.0224 (6)	0.0011 (5)	0.0055 (5)	−0.0020 (5)

N1—C1	1.3469 (15)	C2—C3	1.3446 (17)
N1—N2	1.3635 (14)	C2—C5	1.4958 (16)
N1—N6	1.4119 (14)	C3—C4	1.4615 (17)
N2—N3	1.2874 (15)	C3—H3	0.953 (15)
N3—N4	1.3745 (14)	C4—C6	1.5018 (16)
N4—C1	1.3207 (15)	C5—H5A	0.9600
N5—C1	1.3623 (15)	C5—H5B	0.9600
N5—C2	1.3820 (15)	C5—H5C	0.9600
N5—H5N	0.920 (18)	C6—H6A	0.9600
N6—C4	1.2897 (16)	C6—H6B	0.9600
C1—N1—N2	107.83 (10)	C2—C3—H3	115.8 (9)
C1—N1—N6	137.23 (10)	C4—C3—H3	112.8 (9)
N2—N1—N6	114.45 (9)	N6—C4—C3	132.13 (11)
N3—N2—N1	106.88 (10)	N6—C4—C6	113.82 (10)
N2—N3—N4	110.69 (10)	C3—C4—C6	114.02 (11)
C1—N4—N3	105.82 (10)	C2—C5—H5A	109.5
C1—N5—C2	126.17 (11)	C2—C5—H5B	109.5
C1—N5—H5N	115.3 (10)	H5A—C5—H5B	109.5
C2—N5—H5N	118.4 (10)	C2—C5—H5C	109.5
C4—N6—N1	117.58 (10)	H5A—C5—H5C	109.5
N4—C1—N1	108.78 (10)	H5B—C5—H5C	109.5
N4—C1—N5	122.92 (11)	C4—C6—H6A	109.5
N1—C1—N5	128.29 (11)	C4—C6—H6B	109.5
C3—C2—N5	126.01 (11)	H6A—C6—H6B	109.5
C3—C2—C5	122.01 (11)	C4—C6—H6C	109.5
N5—C2—C5	111.95 (11)	H6A—C6—H6C	109.5
C2—C3—C4	131.03 (12)	H6B—C6—H6C	109.5
C1—N1—N2—N3	0.80 (13)	N6—N1—C1—N5	8.2 (2)
N6—N1—N2—N3	174.17 (10)	C2—N5—C1—N4	−174.90 (12)
N1—N2—N3—N4	−0.47 (14)	C2—N5—C1—N1	5.0 (2)
N2—N3—N4—C1	−0.04 (14)	C1—N5—C2—C3	−4.3 (2)
C1—N1—N6—C4	−12.5 (2)	C1—N5—C2—C5	177.67 (12)
N2—N1—N6—C4	176.81 (10)	N5—C2—C3—C4	−7.1 (2)
N3—N4—C1—N1	0.55 (13)	C5—C2—C3—C4	170.75 (12)
N3—N4—C1—N5	−179.54 (11)	N1—N6—C4—C3	0.64 (19)
N2—N1—C1—N4	−0.84 (14)	N1—N6—C4—C6	178.52 (10)
N6—N1—C1—N4	−171.93 (13)	C2—C3—C4—N6	10.9 (2)
N2—N1—C1—N5	179.24 (12)	C2—C3—C4—C6	−167.02 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N4i	0.920 (19)	1.999 (19)	2.9156 (17)	173.5 (15)

Cgi	Cgj	Cgi···Cgj	α	Cgi_perp	Cgj_perp
Cg1	Cg2i	3.419 (1)	2.83	3.384	3.390

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N4i	0.920 (19)	1.999 (19)	2.9156 (17)	173.5 (15)

Symmetry code: (i) .