5-[4-(1H-Imidazol-1-yl)phen-yl]-1H-tetra-zole.

In the title compound, C(10)H(8)N(6), the tetra-zole and benzene rings are close to being coplanar [dihedral angle = 9.90 (16)°], but the imidazole ring is rotated 37.18 (09)° out of the benzene plane. In the crystal, mol-ecules are connected through tetra-zole-imidazole N-H⋯N hydrogen bonds, giving rise to zigzag chains, which extend along [010].

Related literature

For our previous work based on the imidazole derivatives as ligands, see: Li et al. (2010 ▶); Tong et al. (2011 ▶); Tong et al., (2012 ▶). For related structures, see: Huang et al. (2009 ▶); Cheng (2011 ▶).

Experimental

Crystal data

C10H8N6

M = 212.22

Monoclinic,

a = 3.7219 (12) Å

b = 16.429 (5) Å

c = 7.791 (2) Å

β = 97.167 (6)°

V = 472.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.971, T max = 0.985

3477 measured reflections

1421 independent reflections

1239 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.120

S = 1.35

1421 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812013670/zs2194sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013670/zs2194Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013670/zs2194Isup3.cml

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

C10H8N6	F(000) = 220
Mr = 212.22	Dx = 1.491 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1003 reflections
a = 3.7219 (12) Å	θ = 2.6–22.3°
b = 16.429 (5) Å	µ = 0.10 mm−1
c = 7.791 (2) Å	T = 296 K
β = 97.167 (6)°	Block, colorless
V = 472.6 (3) Å3	0.30 × 0.20 × 0.15 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1421 independent reflections
Radiation source: fine-focus sealed tube	1239 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −4→4
Tmin = 0.971, Tmax = 0.985	k = −19→18
3477 measured reflections	l = −9→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.35	w = 1/[σ2(Fo2) + (0.051P)2 + 0.001P] where P = (Fo2 + 2Fc2)/3
1421 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.31 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	0.9106 (8)	0.45885 (16)	0.5643 (3)	0.0314 (7)
N2	0.9495 (8)	0.57050 (19)	0.7228 (4)	0.0388 (8)
N3	0.3005 (9)	0.16887 (18)	0.0321 (4)	0.0370 (8)
H3	0.2517	0.1475	0.1273	0.044*
N4	0.2320 (10)	0.13459 (19)	−0.1262 (4)	0.0451 (9)
N5	0.3436 (11)	0.1857 (2)	−0.2329 (4)	0.0487 (9)
N6	0.4867 (9)	0.2536 (2)	−0.1484 (4)	0.0422 (8)
C1	0.6945 (10)	0.3256 (2)	0.4631 (4)	0.0350 (9)
H1A	0.6956	0.3095	0.5776	0.042*
C2	0.5860 (10)	0.2723 (2)	0.3310 (4)	0.0352 (9)
H2A	0.5189	0.2195	0.3563	0.042*
C3	0.5757 (9)	0.2967 (2)	0.1594 (4)	0.0276 (8)
C4	0.6843 (9)	0.3746 (2)	0.1250 (4)	0.0326 (8)
H4A	0.6805	0.3911	0.0106	0.039*
C5	0.7988 (9)	0.4287 (2)	0.2560 (4)	0.0330 (9)
H5A	0.8719	0.4810	0.2308	0.040*
C6	0.8024 (9)	0.4037 (2)	0.4249 (4)	0.0287 (8)
C7	0.8324 (9)	0.5391 (2)	0.5711 (4)	0.0350 (9)
H7A	0.7107	0.5684	0.4796	0.042*
C8	1.1139 (10)	0.5070 (2)	0.8171 (4)	0.0359 (9)
H8A	1.2250	0.5110	0.9305	0.043*
C9	1.0919 (10)	0.4384 (2)	0.7229 (4)	0.0338 (8)
H9A	1.1812	0.3873	0.7578	0.041*
C10	0.4558 (10)	0.2411 (2)	0.0171 (4)	0.0310 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0388 (17)	0.0255 (18)	0.0297 (16)	0.0014 (13)	0.0032 (13)	0.0001 (13)
N2	0.050 (2)	0.0313 (17)	0.0346 (16)	0.0023 (15)	0.0045 (14)	−0.0022 (14)
N3	0.0485 (19)	0.0313 (18)	0.0303 (16)	−0.0028 (15)	0.0015 (14)	0.0012 (13)
N4	0.062 (2)	0.0357 (19)	0.0359 (18)	−0.0056 (17)	0.0009 (15)	−0.0041 (15)
N5	0.074 (3)	0.039 (2)	0.0330 (19)	−0.0032 (18)	0.0052 (18)	−0.0041 (16)
N6	0.059 (2)	0.0367 (18)	0.0318 (16)	−0.0055 (16)	0.0080 (15)	−0.0003 (15)
C1	0.047 (2)	0.032 (2)	0.0268 (19)	0.0006 (18)	0.0065 (16)	0.0046 (15)
C2	0.048 (2)	0.027 (2)	0.0317 (19)	−0.0044 (17)	0.0078 (16)	0.0036 (15)
C3	0.0263 (17)	0.0287 (19)	0.0279 (17)	0.0004 (15)	0.0040 (14)	−0.0004 (15)
C4	0.040 (2)	0.034 (2)	0.0249 (19)	−0.0007 (17)	0.0053 (16)	0.0049 (15)
C5	0.038 (2)	0.028 (2)	0.0338 (19)	−0.0045 (17)	0.0094 (16)	0.0049 (15)
C6	0.0290 (19)	0.0288 (19)	0.0281 (18)	0.0000 (16)	0.0027 (15)	−0.0034 (15)
C7	0.037 (2)	0.033 (2)	0.034 (2)	0.0034 (17)	0.0001 (16)	0.0018 (15)
C8	0.039 (2)	0.040 (2)	0.0278 (17)	0.0008 (18)	0.0023 (15)	0.0000 (17)
C9	0.039 (2)	0.031 (2)	0.0293 (18)	0.0042 (17)	−0.0018 (15)	0.0032 (15)
C10	0.0362 (19)	0.029 (2)	0.0281 (19)	−0.0020 (16)	0.0054 (15)	0.0017 (15)

N1—C7	1.353 (4)	C1—H1A	0.9300
N1—C9	1.374 (4)	C2—C3	1.392 (4)
N1—C6	1.433 (4)	C2—H2A	0.9300
N2—C7	1.313 (4)	C3—C4	1.377 (5)
N2—C8	1.376 (5)	C3—C10	1.463 (4)
N3—C10	1.332 (5)	C4—C5	1.381 (5)
N3—N4	1.351 (4)	C4—H4A	0.9300
N3—H3	0.8600	C5—C6	1.377 (4)
N4—N5	1.286 (5)	C5—H5A	0.9300
N5—N6	1.369 (5)	C7—H7A	0.9300
N6—C10	1.324 (4)	C8—C9	1.342 (5)
C1—C2	1.374 (5)	C8—H8A	0.9300
C1—C6	1.387 (5)	C9—H9A	0.9300
C7—N1—C9	106.7 (3)	C3—C4—H4A	119.2
C7—N1—C6	127.2 (3)	C5—C4—H4A	119.2
C9—N1—C6	125.9 (3)	C6—C5—C4	118.7 (3)
C7—N2—C8	105.0 (3)	C6—C5—H5A	120.7
C10—N3—N4	109.0 (3)	C4—C5—H5A	120.7
C10—N3—H3	125.5	C5—C6—C1	120.8 (3)
N4—N3—H3	125.5	C5—C6—N1	120.2 (3)
N5—N4—N3	106.2 (3)	C1—C6—N1	118.9 (3)
N4—N5—N6	111.0 (3)	N2—C7—N1	111.7 (3)
C10—N6—N5	105.4 (3)	N2—C7—H7A	124.2
C2—C1—C6	119.6 (3)	N1—C7—H7A	124.2
C2—C1—H1A	120.2	C9—C8—N2	110.6 (3)
C6—C1—H1A	120.2	C9—C8—H8A	124.7
C1—C2—C3	120.4 (3)	N2—C8—H8A	124.7
C1—C2—H2A	119.8	C8—C9—N1	106.0 (3)
C3—C2—H2A	119.8	C8—C9—H9A	127.0
C4—C3—C2	118.7 (3)	N1—C9—H9A	127.0
C4—C3—C10	120.1 (3)	N6—C10—N3	108.3 (3)
C2—C3—C10	121.1 (3)	N6—C10—C3	125.9 (3)
C3—C4—C5	121.7 (3)	N3—C10—C3	125.8 (3)
C10—N3—N4—N5	−0.2 (4)	C9—N1—C6—C1	35.1 (5)
N3—N4—N5—N6	0.2 (4)	C8—N2—C7—N1	0.5 (4)
N4—N5—N6—C10	−0.1 (5)	C9—N1—C7—N2	−0.4 (4)
C6—C1—C2—C3	−1.5 (5)	C6—N1—C7—N2	175.1 (3)
C1—C2—C3—C4	1.5 (5)	C7—N2—C8—C9	−0.5 (4)
C1—C2—C3—C10	−179.1 (3)	N2—C8—C9—N1	0.3 (4)
C2—C3—C4—C5	−0.7 (5)	C7—N1—C9—C8	0.0 (4)
C10—C3—C4—C5	179.9 (3)	C6—N1—C9—C8	−175.5 (3)
C3—C4—C5—C6	−0.2 (5)	N5—N6—C10—N3	−0.1 (4)
C4—C5—C6—C1	0.2 (5)	N5—N6—C10—C3	179.3 (3)
C4—C5—C6—N1	−178.4 (3)	N4—N3—C10—N6	0.2 (4)
C2—C1—C6—C5	0.7 (5)	N4—N3—C10—C3	−179.2 (3)
C2—C1—C6—N1	179.2 (3)	C4—C3—C10—N6	10.2 (6)
C7—N1—C6—C5	39.0 (5)	C2—C3—C10—N6	−169.2 (4)
C9—N1—C6—C5	−146.3 (3)	C4—C3—C10—N3	−170.6 (3)
C7—N1—C6—C1	−139.6 (4)	C2—C3—C10—N3	10.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	0.86	1.93	2.751 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	0.86	1.93	2.751 (4)	158

Symmetry code: (i) .