5,5'-(p-Phenyl-ene)di-1H-tetra-zole.

Crystals of the title organic compound, C(8)H(6)N(8), were generated in situ through the [2 + 3]-cyclo-addition reaction involving the precursor 1,4-dicyano-benzene and azide in water with Zn(2+) as Lewis acid. The asymmetric unit consists of one half-mol-ecule, and a twofold axis of symmetry passes through the centre of the benzene ring. There is an inter-molecular N-H⋯N hydrogen bond. The mol-ecules are assembled into a three-dimensional supra-molecular framework by π-π stacking inter-actions, with a perpendicular distance of 3.256 Å [centroid-centroid = 3.9731 (8) Å] between two tetra-zole ring planes, and 3.382 Å between the benz-ene ring and tetra-zole ring planes [centroid-centroid = 3.5010 (9) Å].

Related literature

For related literature, see: Demko & Sharpless (2001 ▶, 2002 ▶); Furmeier & Metzger (2003 ▶); Huang et al. (2005 ▶); Wang et al. (2005 ▶); Xiong et al. (2002 ▶); Ye et al. (2005 ▶).

Experimental

Crystal data

C8H6N8

M = 214.21

Monoclinic,

a = 4.5396 (4) Å

b = 9.8219 (10) Å

c = 9.7525 (10) Å

β = 92.910 (5)°

V = 434.28 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.70 × 0.12 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.701, T max = 1.000 (expected range = 0.693–0.988)

3228 measured reflections

985 independent reflections

830 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.106

S = 1.07

985 reflections

73 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Sheldrick, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062538/at2504sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062538/at2504Isup2.hkl

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

C8H6N8	F(000) = 220
Mr = 214.21	Dx = 1.638 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1058 reflections
a = 4.5396 (4) Å	θ = 4.2–27.5°
b = 9.8219 (10) Å	µ = 0.12 mm−1
c = 9.7525 (10) Å	T = 293 K
β = 92.910 (5)°	Prism, colourless
V = 434.28 (7) Å3	0.70 × 0.12 × 0.10 mm
Z = 2

Siemens SMART CCD diffractometer	985 independent reflections
Radiation source: fine-focus sealed tube	830 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: ω pixels mm-1	θmax = 27.5°, θmin = 4.2°
dtprofit.ref scans	h = −5→5
Absorption correction: multi-scan (SADABS; Siemens, 1996)	k = −12→10
Tmin = 0.701, Tmax = 1.000	l = −12→12
3228 measured 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) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.0841P] where P = (Fo2 + 2Fc2)/3
985 reflections	(Δ/σ)max < 0.001
73 parameters	Δρmax = 0.26 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
N1	0.2260 (3)	0.63240 (12)	0.42296 (11)	0.0191 (3)
N2	0.2387 (3)	0.62431 (12)	0.55599 (11)	0.0188 (3)
C9	−0.0803 (3)	0.78246 (13)	0.49215 (12)	0.0138 (3)
C6	−0.2968 (3)	0.89304 (13)	0.49702 (12)	0.0142 (3)
C7	−0.5995 (3)	1.04419 (14)	0.62493 (13)	0.0167 (3)
H7A	−0.6662	1.0738	0.7085	0.020*
C8	−0.3988 (3)	0.93858 (14)	0.62200 (13)	0.0167 (3)
H8A	−0.3312	0.8975	0.7036	0.020*
N4	0.0286 (3)	0.73052 (11)	0.37995 (11)	0.0166 (3)
N3	0.0463 (3)	0.71737 (11)	0.60025 (11)	0.0159 (3)
H3A	0.0108	0.7324	0.6847	0.019*

	U11	U22	U33	U12	U13	U23
N1	0.0222 (7)	0.0192 (6)	0.0159 (6)	0.0010 (5)	0.0004 (5)	−0.0008 (4)
N2	0.0221 (7)	0.0176 (6)	0.0167 (6)	0.0014 (5)	0.0015 (5)	−0.0015 (4)
C9	0.0145 (7)	0.0150 (7)	0.0118 (6)	−0.0047 (5)	−0.0007 (5)	0.0003 (4)
C6	0.0141 (6)	0.0150 (6)	0.0133 (6)	−0.0033 (5)	−0.0009 (5)	0.0007 (5)
C7	0.0199 (7)	0.0198 (7)	0.0105 (6)	−0.0001 (6)	0.0014 (5)	−0.0007 (5)
C8	0.0190 (7)	0.0197 (7)	0.0113 (6)	−0.0002 (5)	−0.0010 (5)	0.0027 (5)
N4	0.0190 (6)	0.0179 (6)	0.0129 (5)	0.0002 (5)	0.0000 (4)	−0.0006 (4)
N3	0.0194 (6)	0.0172 (6)	0.0112 (5)	0.0008 (5)	0.0012 (4)	−0.0002 (4)

N1—N2	1.2982 (16)	C6—C8	1.3991 (18)
N1—N4	1.3674 (16)	C7—C8	1.3819 (19)
N2—N3	1.3499 (16)	C7—C6i	1.3997 (17)
C9—N4	1.3256 (17)	C7—H7A	0.9300
C9—N3	1.3376 (16)	C8—H8A	0.9300
C9—C6	1.4672 (18)	N3—H3A	0.8600
C6—C7i	1.3997 (17)
N2—N1—N4	110.17 (11)	C8—C7—H7A	119.8
N1—N2—N3	106.36 (10)	C6i—C7—H7A	119.8
N4—C9—N3	107.65 (12)	C7—C8—C6	120.38 (12)
N4—C9—C6	126.17 (11)	C7—C8—H8A	119.8
N3—C9—C6	126.17 (12)	C6—C8—H8A	119.8
C7i—C6—C8	119.18 (13)	C9—N4—N1	106.51 (10)
C7i—C6—C9	119.70 (12)	C9—N3—N2	109.31 (11)
C8—C6—C9	121.11 (12)	C9—N3—H3A	125.3
C8—C7—C6i	120.44 (12)	N2—N3—H3A	125.3
N4—N1—N2—N3	0.39 (14)	C9—C6—C8—C7	179.05 (12)
N4—C9—C6—C7i	−1.7 (2)	N3—C9—N4—N1	−0.25 (15)
N3—C9—C6—C7i	177.09 (13)	C6—C9—N4—N1	178.76 (12)
N4—C9—C6—C8	179.24 (13)	N2—N1—N4—C9	−0.09 (15)
N3—C9—C6—C8	−1.9 (2)	N4—C9—N3—N2	0.50 (15)
C6i—C7—C8—C6	0.0 (2)	C6—C9—N3—N2	−178.51 (12)
C7i—C6—C8—C7	0.0 (2)	N1—N2—N3—C9	−0.55 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4ii	0.86	1.94	2.7805 (15)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N4i	0.86	1.94	2.7805 (15)	167

Symmetry code: (i) .