4-[5-(3-Pyrid-yl)-2H-tetra-zol-2-ylmeth-yl]benzonitrile.

In the title compound, C(14)H(10)N(6), the pyridine and tetra-zole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 0.86 (9)°. The benzene ring makes a dihedral angle of 70.55 (6)° with the tetra-zole ring.

Related literature

For the use of tetra­zole derivatives in coordination chemisty, see: Arp et al. (2000 ▶); Hu et al. (2007 ▶); Wang et al. (2005 ▶); Xiong et al. (2002 ▶).

Experimental

Crystal data

C14H10N6

M = 262.28

Triclinic,

a = 8.0452 (16) Å

b = 8.7081 (17) Å

c = 10.171 (2) Å

α = 94.61 (3)°

β = 104.95 (3)°

γ = 111.11 (3)°

V = 630.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.4 × 0.35 × 0.35 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.962, T max = 0.968

6638 measured reflections

2882 independent reflections

2063 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.123

S = 1.04

2882 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009550/dn2333sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009550/dn2333Isup2.hkl

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

C14H10N6	Z = 2
Mr = 262.28	F000 = 272
Triclinic, P1	Dx = 1.382 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0452 (16) Å	Cell parameters from 2882 reflections
b = 8.7081 (17) Å	θ = 3.4–27.5º
c = 10.171 (2) Å	µ = 0.09 mm−1
α = 94.61 (3)º	T = 293 (2) K
β = 104.95 (3)º	Block, colourless
γ = 111.11 (3)º	0.4 × 0.35 × 0.35 mm
V = 630.3 (3) Å3

Rigaku Mercury2 diffractometer	2882 independent reflections
Radiation source: fine-focus sealed tube	2063 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.4º
ω scans	h = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.962, Tmax = 0.968	l = −13→13
6638 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.0983P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2882 reflections	Δρmax = 0.17 e Å−3
181 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.1058 (3)	−0.1591 (2)	0.5558 (2)	0.0572 (5)
H1	0.0253	−0.2512	0.5801	0.069*
C2	0.2506 (3)	−0.0395 (2)	0.65976 (19)	0.0573 (5)
H2	0.2661	−0.0497	0.7520	0.069*
C3	0.3732 (2)	0.0965 (2)	0.62507 (17)	0.0492 (4)
H3	0.4736	0.1790	0.6936	0.059*
C4	0.3447 (2)	0.10834 (19)	0.48717 (15)	0.0379 (3)
C5	0.1926 (2)	−0.0186 (2)	0.39132 (18)	0.0503 (4)
H5	0.1717	−0.0109	0.2983	0.060*
C6	0.4708 (2)	0.24879 (19)	0.44434 (15)	0.0389 (4)
C7	0.6451 (3)	0.4856 (2)	0.2136 (2)	0.0558 (5)
H7A	0.7176	0.6053	0.2454	0.067*
H7B	0.5309	0.4698	0.1420	0.067*
C8	0.7564 (2)	0.4087 (2)	0.15309 (17)	0.0443 (4)
C9	0.9485 (2)	0.4701 (2)	0.21250 (18)	0.0493 (4)
H9	1.0070	0.5578	0.2888	0.059*
C10	1.0544 (2)	0.4029 (2)	0.16004 (17)	0.0474 (4)
H10	1.1835	0.4445	0.2011	0.057*
C11	0.9677 (2)	0.2733 (2)	0.04600 (16)	0.0417 (4)
C12	0.7746 (2)	0.2088 (2)	−0.01356 (17)	0.0513 (4)
H12	0.7162	0.1201	−0.0892	0.062*
C13	0.6696 (2)	0.2767 (2)	0.03990 (18)	0.0523 (4)
H13	0.5403	0.2340	0.0000	0.063*
C14	1.0826 (2)	0.2107 (2)	−0.01146 (17)	0.0490 (4)
N1	0.0737 (2)	−0.15148 (18)	0.42275 (17)	0.0583 (4)
N2	0.45326 (18)	0.26697 (17)	0.31385 (13)	0.0448 (3)
N3	0.59763 (19)	0.41048 (17)	0.32955 (14)	0.0455 (3)
N4	0.6996 (2)	0.47768 (19)	0.45939 (16)	0.0551 (4)
N5	0.61961 (19)	0.37565 (18)	0.53498 (14)	0.0514 (4)
N6	1.1781 (2)	0.1676 (2)	−0.05615 (16)	0.0654 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0591 (11)	0.0495 (10)	0.0713 (13)	0.0216 (9)	0.0306 (10)	0.0206 (9)
C2	0.0666 (12)	0.0641 (12)	0.0495 (10)	0.0281 (10)	0.0255 (9)	0.0203 (9)
C3	0.0496 (10)	0.0522 (10)	0.0430 (9)	0.0188 (8)	0.0125 (8)	0.0065 (7)
C4	0.0371 (8)	0.0419 (8)	0.0386 (8)	0.0188 (7)	0.0144 (7)	0.0053 (6)
C5	0.0526 (10)	0.0491 (10)	0.0444 (9)	0.0150 (8)	0.0159 (8)	0.0054 (7)
C6	0.0354 (8)	0.0438 (9)	0.0394 (8)	0.0169 (7)	0.0140 (7)	0.0029 (7)
C7	0.0618 (11)	0.0595 (11)	0.0698 (12)	0.0333 (10)	0.0402 (10)	0.0299 (9)
C8	0.0468 (9)	0.0490 (9)	0.0487 (9)	0.0224 (8)	0.0255 (8)	0.0201 (8)
C9	0.0491 (10)	0.0486 (10)	0.0475 (9)	0.0146 (8)	0.0186 (8)	0.0044 (8)
C10	0.0364 (8)	0.0534 (10)	0.0496 (9)	0.0144 (8)	0.0144 (8)	0.0074 (8)
C11	0.0406 (9)	0.0491 (9)	0.0384 (8)	0.0182 (7)	0.0154 (7)	0.0109 (7)
C12	0.0438 (9)	0.0598 (11)	0.0427 (9)	0.0165 (8)	0.0093 (8)	0.0009 (8)
C13	0.0371 (9)	0.0664 (11)	0.0541 (10)	0.0197 (8)	0.0157 (8)	0.0137 (9)
C14	0.0450 (9)	0.0571 (10)	0.0426 (9)	0.0189 (8)	0.0125 (8)	0.0064 (8)
N1	0.0565 (9)	0.0442 (8)	0.0663 (10)	0.0107 (7)	0.0201 (8)	0.0074 (7)
N2	0.0430 (8)	0.0487 (8)	0.0437 (8)	0.0157 (6)	0.0188 (6)	0.0089 (6)
N3	0.0428 (8)	0.0474 (8)	0.0531 (8)	0.0184 (7)	0.0246 (7)	0.0121 (7)
N4	0.0447 (8)	0.0538 (9)	0.0591 (9)	0.0095 (7)	0.0194 (7)	0.0059 (7)
N5	0.0437 (8)	0.0523 (8)	0.0502 (8)	0.0097 (7)	0.0162 (7)	0.0055 (7)
N6	0.0581 (10)	0.0839 (12)	0.0611 (10)	0.0351 (9)	0.0227 (8)	0.0040 (9)

C1—N1	1.322 (2)	C7—H7B	0.9700
C1—C2	1.369 (3)	C8—C9	1.382 (2)
C1—H1	0.9300	C8—C13	1.389 (3)
C2—C3	1.381 (3)	C9—C10	1.377 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.380 (2)	C10—C11	1.383 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.381 (2)	C11—C12	1.389 (2)
C4—C6	1.461 (2)	C11—C14	1.443 (2)
C5—N1	1.332 (2)	C12—C13	1.380 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—N2	1.3265 (19)	C13—H13	0.9300
C6—N5	1.348 (2)	C14—N6	1.140 (2)
C7—N3	1.464 (2)	N2—N3	1.3277 (19)
C7—C8	1.509 (2)	N3—N4	1.315 (2)
C7—H7A	0.9700	N4—N5	1.322 (2)
N1—C1—C2	123.89 (17)	C9—C8—C7	119.23 (16)
N1—C1—H1	118.1	C13—C8—C7	121.38 (16)
C2—C1—H1	118.1	C10—C9—C8	120.79 (16)
C1—C2—C3	118.73 (17)	C10—C9—H9	119.6
C1—C2—H2	120.6	C8—C9—H9	119.6
C3—C2—H2	120.6	C9—C10—C11	119.63 (15)
C4—C3—C2	119.00 (17)	C9—C10—H10	120.2
C4—C3—H3	120.5	C11—C10—H10	120.2
C2—C3—H3	120.5	C10—C11—C12	120.21 (15)
C3—C4—C5	117.22 (15)	C10—C11—C14	118.62 (15)
C3—C4—C6	121.38 (15)	C12—C11—C14	121.14 (15)
C5—C4—C6	121.40 (14)	C13—C12—C11	119.73 (16)
N1—C5—C4	124.61 (16)	C13—C12—H12	120.1
N1—C5—H5	117.7	C11—C12—H12	120.1
C4—C5—H5	117.7	C12—C13—C8	120.24 (16)
N2—C6—N5	112.35 (14)	C12—C13—H13	119.9
N2—C6—C4	124.60 (14)	C8—C13—H13	119.9
N5—C6—C4	123.05 (14)	N6—C14—C11	177.31 (19)
N3—C7—C8	111.58 (13)	C1—N1—C5	116.53 (16)
N3—C7—H7A	109.3	C6—N2—N3	101.60 (13)
C8—C7—H7A	109.3	N4—N3—N2	114.04 (13)
N3—C7—H7B	109.3	N4—N3—C7	122.32 (15)
C8—C7—H7B	109.3	N2—N3—C7	123.60 (15)
H7A—C7—H7B	108.0	N3—N4—N5	106.02 (13)
C9—C8—C13	119.38 (16)	N4—N5—C6	105.98 (13)