4-[(2H-Tetra-zol-2-yl)meth-yl]benzonitrile.

The title compound, C(9)H(7)N(5), was synthesized by reaction of 4-(bromomethyl)benzonitrile and 2H-tetrazole in the presence of KOH. The relative orientation of the planar tetra-zole ring and the methyl-benzonitrile moiety is (-)-anti-clinal. The crystal packing is dominated by van der Waals inter-actions.

Related literature

For the chemisty of tetra­zoles, see: Bethel et al. (1999 ▶); Wu et al. (2005 ▶); Zhang et al. (2006 ▶); Jin et al. (1994 ▶).

Experimental

Crystal data

C9H7N5

M = 185.20

Triclinic,

a = 5.7514 (8) Å

b = 7.4029 (10) Å

c = 11.3511 (12) Å

α = 81.088 (3)°

β = 77.844 (3)°

γ = 72.600 (5)°

V = 448.64 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.20 × 0.12 × 0.02 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.980, T max = 0.996

4114 measured reflections

1720 independent reflections

923 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.156

S = 0.92

1720 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 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, global. DOI: 10.1107/S1600536808000809/kp2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000809/kp2157Isup2.hkl

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

C9H7N5	Z = 2
Mr = 185.20	F000 = 192
Triclinic, P1	Dx = 1.371 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.7514 (8) Å	Cell parameters from 655 reflections
b = 7.4029 (10) Å	θ = 3.3–27.4º
c = 11.3511 (12) Å	µ = 0.09 mm−1
α = 81.088 (3)º	T = 293 (2) K
β = 77.844 (3)º	Block, colourless
γ = 72.600 (5)º	0.20 × 0.12 × 0.02 mm
V = 448.64 (10) Å3

Rigaku Mercury2 diffractometer	1720 independent reflections
Radiation source: fine-focus sealed tube	923 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 3.3º
CCD_Profile_fitting scans	h = −7→7
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.980, Tmax = 0.996	l = −13→13
4114 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)] = 0.053	w = 1/[σ2(Fo2) + (0.0718P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.156	(Δ/σ)max < 0.001
S = 0.92	Δρmax = 0.17 e Å−3
1720 reflections	Δρmin = −0.16 e Å−3
132 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Secondary atom site location: difference Fourier map	Extinction coefficient: 0.044 (14)

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
N2	1.0618 (5)	0.2439 (4)	0.4265 (2)	0.0821 (8)
C1	0.3315 (4)	0.9248 (4)	0.9005 (2)	0.0554 (6)
C2	0.4374 (4)	0.7403 (3)	0.8573 (2)	0.0502 (6)
C3	0.6613 (4)	0.6272 (3)	0.8855 (2)	0.0547 (7)
H3	0.7445	0.6703	0.9324	0.066*
C4	0.7606 (4)	0.4506 (3)	0.8438 (2)	0.0560 (7)
H4	0.9121	0.3749	0.8622	0.067*
C5	0.6377 (4)	0.3841 (3)	0.7748 (2)	0.0525 (6)
C6	0.4133 (5)	0.4976 (4)	0.7479 (2)	0.0621 (7)
H6	0.3292	0.4541	0.7018	0.075*
C7	0.3128 (5)	0.6752 (4)	0.7891 (2)	0.0606 (7)
H7	0.1613	0.7510	0.7708	0.073*
C8	0.7485 (5)	0.1932 (3)	0.7266 (2)	0.0611 (7)
H8A	0.8329	0.1040	0.7865	0.073*
H8B	0.6176	0.1460	0.7124	0.073*
N1	0.8605 (4)	0.2339 (4)	0.5064 (2)	0.0764 (7)
C9	1.2358 (6)	0.2213 (5)	0.4920 (3)	0.0730 (9)
N3	1.1596 (4)	0.1945 (3)	0.6083 (2)	0.0703 (7)
N4	0.9239 (4)	0.2044 (3)	0.61371 (17)	0.0550 (6)
N5	0.2481 (4)	1.0719 (3)	0.9343 (2)	0.0770 (8)
H9	1.385 (6)	0.208 (5)	0.462 (3)	0.116 (13)*

	U11	U22	U33	U12	U13	U23
N2	0.0782 (17)	0.103 (2)	0.0630 (15)	−0.0277 (15)	−0.0037 (14)	−0.0081 (13)
C1	0.0509 (14)	0.0546 (15)	0.0616 (16)	−0.0117 (13)	−0.0132 (12)	−0.0098 (13)
C2	0.0510 (14)	0.0511 (14)	0.0485 (13)	−0.0148 (12)	−0.0083 (11)	−0.0038 (11)
C3	0.0527 (15)	0.0602 (16)	0.0554 (15)	−0.0151 (12)	−0.0162 (12)	−0.0101 (12)
C4	0.0481 (14)	0.0594 (15)	0.0569 (15)	−0.0083 (12)	−0.0081 (12)	−0.0091 (12)
C5	0.0569 (15)	0.0506 (14)	0.0493 (14)	−0.0184 (12)	−0.0030 (12)	−0.0045 (11)
C6	0.0635 (17)	0.0629 (17)	0.0672 (17)	−0.0183 (14)	−0.0200 (13)	−0.0144 (13)
C7	0.0489 (14)	0.0657 (17)	0.0690 (17)	−0.0118 (12)	−0.0165 (12)	−0.0113 (13)
C8	0.0634 (16)	0.0532 (15)	0.0625 (15)	−0.0163 (13)	0.0032 (13)	−0.0118 (12)
N1	0.0705 (16)	0.0940 (18)	0.0654 (15)	−0.0193 (14)	−0.0167 (13)	−0.0102 (13)
C9	0.063 (2)	0.087 (2)	0.070 (2)	−0.0270 (17)	0.0022 (17)	−0.0190 (16)
N3	0.0574 (14)	0.0879 (17)	0.0730 (16)	−0.0225 (12)	−0.0144 (12)	−0.0204 (13)
N4	0.0550 (13)	0.0549 (12)	0.0575 (13)	−0.0148 (10)	−0.0104 (10)	−0.0124 (10)
N5	0.0703 (16)	0.0659 (16)	0.0962 (18)	−0.0046 (13)	−0.0285 (13)	−0.0211 (13)

N2—C9	1.326 (4)	C5—C8	1.502 (3)
N2—N1	1.325 (3)	C6—C7	1.380 (3)
C1—N5	1.141 (3)	C6—H6	0.9300
C1—C2	1.436 (3)	C7—H7	0.9300
C2—C7	1.379 (3)	C8—N4	1.463 (3)
C2—C3	1.381 (3)	C8—H8A	0.9700
C3—C4	1.375 (3)	C8—H8B	0.9700
C3—H3	0.9300	N1—N4	1.312 (3)
C4—C5	1.384 (3)	C9—N3	1.304 (3)
C4—H4	0.9300	C9—H9	0.84 (3)
C5—C6	1.379 (3)	N3—N4	1.324 (3)
C9—N2—N1	105.1 (2)	C2—C7—C6	119.9 (2)
N5—C1—C2	179.6 (3)	C2—C7—H7	120.0
C7—C2—C3	120.1 (2)	C6—C7—H7	120.0
C7—C2—C1	119.7 (2)	N4—C8—C5	111.39 (19)
C3—C2—C1	120.2 (2)	N4—C8—H8A	109.4
C4—C3—C2	119.6 (2)	C5—C8—H8A	109.4
C4—C3—H3	120.2	N4—C8—H8B	109.4
C2—C3—H3	120.2	C5—C8—H8B	109.4
C3—C4—C5	120.8 (2)	H8A—C8—H8B	108.0
C3—C4—H4	119.6	N4—N1—N2	106.5 (2)
C5—C4—H4	119.6	N3—C9—N2	113.6 (3)
C6—C5—C4	119.2 (2)	N3—C9—H9	122 (3)
C6—C5—C8	120.0 (2)	N2—C9—H9	124 (2)
C4—C5—C8	120.9 (2)	C9—N3—N4	102.1 (2)
C5—C6—C7	120.5 (2)	N1—N4—N3	112.7 (2)
C5—C6—H6	119.8	N1—N4—C8	123.1 (2)
C7—C6—H6	119.8	N3—N4—C8	124.1 (2)
C7—C2—C3—C4	0.8 (4)	C4—C5—C8—N4	−83.5 (3)
C1—C2—C3—C4	179.9 (2)	C9—N2—N1—N4	−0.6 (3)
C2—C3—C4—C5	−0.6 (4)	N1—N2—C9—N3	1.0 (3)
C3—C4—C5—C6	0.1 (4)	N2—C9—N3—N4	−1.0 (3)
C3—C4—C5—C8	178.5 (2)	N2—N1—N4—N3	0.0 (3)
C4—C5—C6—C7	0.1 (4)	N2—N1—N4—C8	177.3 (2)
C8—C5—C6—C7	−178.3 (2)	C9—N3—N4—N1	0.6 (3)
C3—C2—C7—C6	−0.6 (4)	C9—N3—N4—C8	−176.6 (2)
C1—C2—C7—C6	−179.7 (2)	C5—C8—N4—N1	−92.0 (3)
C5—C6—C7—C2	0.1 (4)	C5—C8—N4—N3	84.9 (3)
C6—C5—C8—N4	94.9 (3)