2-(1H-Tetra-zol-5-yl)benzonitrile.

The title compound, C(8)H(5)N(5), was synthesized from phthalonitrile. The benzonitrile and tetra-zole rings are inclined at a dihedral angle of 37.14 (11)°. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds link the tetra-zole rings of adjacent mol-ecules, forming chains along the a axis.

Related literature

For backgound to the chemisty of tetra­zoles, see: Bekhit et al. (2004 ▶); Aykut İkizler & Sancak (1992 ▶, 1995 ▶, 1998 ▶); Rajasekaran & Thampi (2004 ▶); Satyanarayana et al. (2006 ▶); Schmidt & Schieffer (2003 ▶); Upadhayaya et al. (2004 ▶); Wexler et al. (1996 ▶).

Experimental

Crystal data

C8H5N5

M = 171.17

Monoclinic,

a = 4.9281 (10) Å

b = 6.5420 (13) Å

c = 24.867 (5) Å

β = 95.27 (3)°

V = 798.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.25 × 0.07 × 0.07 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.993, T max = 0.996

6844 measured reflections

1553 independent reflections

1167 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.138

S = 1.10

1553 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808008027/sj2471sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008027/sj2471Isup2.hkl

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

C8H5N5	F000 = 352
Mr = 171.17	Dx = 1.424 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6584 reflections
a = 4.9281 (10) Å	θ = 3.1–28.8º
b = 6.5420 (13) Å	µ = 0.10 mm−1
c = 24.867 (5) Å	T = 293 (2) K
β = 95.27 (3)º	Prism, colorless
V = 798.3 (3) Å3	0.25 × 0.07 × 0.07 mm
Z = 4

Rigaku SCXmini diffractometer	1553 independent reflections
Radiation source: fine-focus sealed tube	1167 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 3.2º
ω scans	h = −6→6
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.993, Tmax = 0.996	l = −30→30
6844 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.055	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.1285P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.21 e Å−3
1553 reflections	Δρmin = −0.24 e Å−3
122 parameters	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (14)
Secondary atom site location: difference Fourier map

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	0.5249 (4)	0.5054 (3)	0.13602 (8)	0.0345 (5)
C2	0.6569 (4)	0.5277 (3)	0.08892 (8)	0.0403 (5)
C3	0.6021 (5)	0.6960 (4)	0.05536 (10)	0.0548 (7)
H3	0.6925	0.7116	0.0244	0.066*
C4	0.4141 (5)	0.8390 (4)	0.06821 (11)	0.0608 (7)
H4	0.3762	0.9509	0.0457	0.073*
C5	0.2821 (5)	0.8174 (4)	0.11410 (11)	0.0539 (6)
H5	0.1537	0.9140	0.1223	0.065*
C6	0.3384 (4)	0.6532 (3)	0.14819 (9)	0.0441 (6)
H6	0.2504	0.6416	0.1796	0.053*
C7	0.5736 (4)	0.3299 (3)	0.17202 (8)	0.0323 (5)
C8	0.8482 (5)	0.3773 (4)	0.07280 (9)	0.0476 (6)
N1	0.9990 (5)	0.2612 (4)	0.05847 (9)	0.0701 (7)
N2	0.3814 (3)	0.2405 (3)	0.19806 (7)	0.0399 (5)
N3	0.4920 (3)	0.0893 (3)	0.22916 (8)	0.0480 (5)
N4	0.7498 (3)	0.0881 (3)	0.22217 (7)	0.0458 (5)
N5	0.8068 (3)	0.2363 (3)	0.18650 (7)	0.0380 (5)
H2	0.195 (6)	0.253 (4)	0.1939 (10)	0.072 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0263 (10)	0.0405 (11)	0.0363 (11)	0.0019 (9)	0.0016 (8)	0.0010 (9)
C2	0.0345 (12)	0.0463 (12)	0.0407 (12)	0.0040 (10)	0.0062 (9)	0.0018 (10)
C3	0.0598 (16)	0.0595 (15)	0.0473 (14)	0.0110 (12)	0.0171 (12)	0.0137 (12)
C4	0.0658 (17)	0.0558 (15)	0.0611 (17)	0.0139 (13)	0.0072 (14)	0.0187 (13)
C5	0.0491 (14)	0.0480 (14)	0.0642 (16)	0.0144 (11)	0.0041 (12)	−0.0003 (12)
C6	0.0397 (12)	0.0507 (13)	0.0425 (13)	0.0070 (10)	0.0069 (10)	−0.0014 (10)
C7	0.0221 (9)	0.0434 (11)	0.0319 (11)	0.0004 (8)	0.0055 (8)	−0.0021 (9)
C8	0.0476 (13)	0.0573 (15)	0.0395 (13)	0.0069 (12)	0.0127 (10)	0.0069 (11)
N1	0.0705 (15)	0.0809 (15)	0.0623 (15)	0.0288 (13)	0.0242 (12)	0.0062 (12)
N2	0.0203 (9)	0.0531 (11)	0.0468 (11)	0.0024 (8)	0.0058 (8)	0.0107 (8)
N3	0.0306 (9)	0.0600 (12)	0.0540 (12)	0.0029 (9)	0.0074 (8)	0.0166 (10)
N4	0.0296 (9)	0.0583 (12)	0.0494 (11)	0.0047 (8)	0.0042 (8)	0.0139 (9)
N5	0.0238 (8)	0.0510 (10)	0.0400 (10)	0.0035 (8)	0.0065 (7)	0.0070 (8)

C1—C6	1.386 (3)	C5—H5	0.9300
C1—C2	1.399 (3)	C6—H6	0.9300
C1—C7	1.462 (3)	C7—N5	1.323 (2)
C2—C3	1.393 (3)	C7—N2	1.331 (2)
C2—C8	1.445 (3)	C8—N1	1.142 (3)
C3—C4	1.375 (3)	N2—N3	1.340 (2)
C3—H3	0.9300	N2—H2	0.92 (3)
C4—C5	1.372 (3)	N3—N4	1.298 (2)
C4—H4	0.9300	N4—N5	1.361 (2)
C5—C6	1.381 (3)
C6—C1—C2	118.61 (19)	C6—C5—H5	119.8
C6—C1—C7	119.24 (18)	C5—C6—C1	120.5 (2)
C2—C1—C7	122.13 (17)	C5—C6—H6	119.7
C3—C2—C1	120.31 (19)	C1—C6—H6	119.7
C3—C2—C8	117.86 (19)	N5—C7—N2	107.65 (17)
C1—C2—C8	121.81 (19)	N5—C7—C1	128.31 (17)
C4—C3—C2	119.7 (2)	N2—C7—C1	123.99 (17)
C4—C3—H3	120.1	N1—C8—C2	177.8 (2)
C2—C3—H3	120.1	C7—N2—N3	109.61 (16)
C5—C4—C3	120.3 (2)	C7—N2—H2	130.9 (16)
C5—C4—H4	119.9	N3—N2—H2	118.7 (16)
C3—C4—H4	119.9	N4—N3—N2	106.16 (16)
C4—C5—C6	120.5 (2)	N3—N4—N5	110.25 (16)
C4—C5—H5	119.8	C7—N5—N4	106.33 (15)
C6—C1—C2—C3	0.4 (3)	C6—C1—C7—N5	−141.7 (2)
C7—C1—C2—C3	179.22 (19)	C2—C1—C7—N5	39.5 (3)
C6—C1—C2—C8	−178.3 (2)	C6—C1—C7—N2	35.6 (3)
C7—C1—C2—C8	0.5 (3)	C2—C1—C7—N2	−143.2 (2)
C1—C2—C3—C4	−1.1 (4)	N5—C7—N2—N3	−0.1 (2)
C8—C2—C3—C4	177.7 (2)	C1—C7—N2—N3	−177.85 (18)
C2—C3—C4—C5	0.5 (4)	C7—N2—N3—N4	0.3 (2)
C3—C4—C5—C6	0.7 (4)	N2—N3—N4—N5	−0.4 (2)
C4—C5—C6—C1	−1.3 (4)	N2—C7—N5—N4	−0.2 (2)
C2—C1—C6—C5	0.8 (3)	C1—C7—N5—N4	177.48 (19)
C7—C1—C6—C5	−178.05 (19)	N3—N4—N5—C7	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N5i	0.92 (3)	1.91 (3)	2.820 (2)	172 (2)
N2—H2···N4i	0.92 (3)	2.60 (3)	3.374 (2)	142 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N5i	0.92 (3)	1.91 (3)	2.820 (2)	172 (2)
N2—H2⋯N4i	0.92 (3)	2.60 (3)	3.374 (2)	142 (2)

Symmetry code: (i) .