1-(4-Methyl-phen-yl)-1H-1,2,3,4-tetra-zole.

In the title compound, C(8)H(8)N(4), the dihedral angle between the tetra-zole and benzene rings is 21.6 (1)°. An inter-molecular C-H⋯π inter-action is observed.

Related literature

For background to and applications of tetra­zole derivatives, see: Singh et al. (1980 ▶); Brown (1967 ▶); Ostrovskii et al. (1999 ▶). For the synthesis, see: Aridoss & Laali (2011 ▶). For related structures, see: Matsunaga et al. (1999 ▶); Lyakhov et al. (2000 ▶).

Experimental

Crystal data

C8H8N4

M = 160.18

Monoclinic,

a = 9.8352 (13) Å

b = 5.7244 (6) Å

c = 14.4190 (19) Å

β = 96.285 (12)°

V = 806.92 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.762, T max = 1.000

14618 measured reflections

1419 independent reflections

936 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.211

S = 1.05

1419 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000797/is5047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000797/is5047Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000797/is5047Isup3.cml

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

C8H8N4	F(000) = 336
Mr = 160.18	Dx = 1.319 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3527 reflections
a = 9.8352 (13) Å	θ = 3.6–29.2°
b = 5.7244 (6) Å	µ = 0.09 mm−1
c = 14.4190 (19) Å	T = 293 K
β = 96.285 (12)°	Plate, white
V = 806.92 (17) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1419 independent reflections
Radiation source: fine-focus sealed tube	936 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.8°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.762, Tmax = 1.000	l = −17→17
14618 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1133P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
1419 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.7153 (3)	0.0846 (5)	0.8500 (2)	0.0726 (9)
H1	0.7271	−0.0729	0.8372	0.087*
C2	0.4656 (3)	0.0810 (4)	0.87347 (17)	0.0540 (7)
C3	0.3730 (3)	0.1934 (5)	0.92335 (18)	0.0635 (8)
H3	0.3959	0.3336	0.9537	0.076*
C4	0.2465 (3)	0.0950 (5)	0.9274 (2)	0.0672 (9)
H4	0.1838	0.1718	0.9605	0.081*
C5	0.2090 (3)	−0.1143 (5)	0.88414 (19)	0.0622 (8)
C6	0.3039 (3)	−0.2219 (5)	0.8337 (2)	0.0634 (8)
H6	0.2811	−0.3625	0.8036	0.076*
C7	0.4315 (3)	−0.1253 (4)	0.82696 (18)	0.0607 (8)
H7	0.4932	−0.1980	0.7918	0.073*
C8	0.0709 (3)	−0.2228 (6)	0.8897 (2)	0.0850 (10)
H8A	0.0534	−0.2328	0.9538	0.127*
H8B	0.0692	−0.3767	0.8631	0.127*
H8C	0.0017	−0.1283	0.8558	0.127*
N1	0.8114 (3)	0.2424 (5)	0.85255 (19)	0.0841 (9)
N2	0.7502 (3)	0.4443 (5)	0.8748 (2)	0.0874 (9)
N3	0.6234 (3)	0.4089 (4)	0.8848 (2)	0.0826 (9)
N4	0.5985 (2)	0.1809 (4)	0.86824 (14)	0.0580 (7)

	U11	U22	U33	U12	U13	U23
C1	0.077 (2)	0.0625 (18)	0.081 (2)	0.0000 (16)	0.0255 (17)	−0.0042 (15)
C2	0.0584 (16)	0.0504 (15)	0.0528 (15)	0.0089 (11)	0.0041 (12)	0.0054 (11)
C3	0.079 (2)	0.0557 (16)	0.0568 (17)	0.0051 (14)	0.0129 (14)	−0.0082 (13)
C4	0.071 (2)	0.0697 (19)	0.0636 (18)	0.0125 (15)	0.0181 (15)	−0.0055 (14)
C5	0.0616 (18)	0.0644 (17)	0.0609 (17)	0.0079 (13)	0.0075 (14)	0.0067 (13)
C6	0.0678 (18)	0.0531 (16)	0.0686 (18)	0.0045 (13)	0.0046 (14)	−0.0049 (13)
C7	0.0661 (19)	0.0524 (15)	0.0635 (18)	0.0138 (13)	0.0073 (14)	−0.0052 (12)
C8	0.066 (2)	0.101 (3)	0.088 (2)	−0.0003 (17)	0.0104 (17)	−0.0046 (19)
N1	0.0828 (19)	0.086 (2)	0.087 (2)	−0.0101 (15)	0.0223 (15)	0.0017 (14)
N2	0.085 (2)	0.0721 (18)	0.106 (2)	−0.0069 (15)	0.0121 (16)	0.0022 (15)
N3	0.082 (2)	0.0569 (16)	0.108 (2)	0.0002 (13)	0.0060 (16)	−0.0030 (13)
N4	0.0649 (15)	0.0519 (13)	0.0568 (14)	0.0047 (11)	0.0048 (11)	0.0029 (10)

C1—N1	1.304 (4)	C5—C8	1.504 (4)
C1—N4	1.326 (3)	C6—C7	1.385 (4)
C1—H1	0.9300	C6—H6	0.9300
C2—C3	1.380 (4)	C7—H7	0.9300
C2—C7	1.381 (4)	C8—H8A	0.9600
C2—N4	1.436 (3)	C8—H8B	0.9600
C3—C4	1.373 (4)	C8—H8C	0.9600
C3—H3	0.9300	N1—N2	1.357 (4)
C4—C5	1.382 (4)	N2—N3	1.288 (4)
C4—H4	0.9300	N3—N4	1.345 (3)
C5—C6	1.389 (4)
N1—C1—N4	110.3 (3)	C5—C6—H6	119.1
N1—C1—H1	124.8	C2—C7—C6	118.8 (3)
N4—C1—H1	124.8	C2—C7—H7	120.6
C3—C2—C7	120.8 (3)	C6—C7—H7	120.6
C3—C2—N4	119.9 (2)	C5—C8—H8A	109.5
C7—C2—N4	119.2 (2)	C5—C8—H8B	109.5
C4—C3—C2	119.0 (3)	H8A—C8—H8B	109.5
C4—C3—H3	120.5	C5—C8—H8C	109.5
C2—C3—H3	120.5	H8A—C8—H8C	109.5
C3—C4—C5	122.3 (2)	H8B—C8—H8C	109.5
C3—C4—H4	118.8	C1—N1—N2	105.0 (3)
C5—C4—H4	118.8	N3—N2—N1	110.6 (2)
C4—C5—C6	117.4 (3)	N2—N3—N4	107.0 (2)
C4—C5—C8	122.1 (3)	C1—N4—N3	107.1 (2)
C6—C5—C8	120.5 (3)	C1—N4—C2	131.2 (2)
C7—C6—C5	121.7 (3)	N3—N4—C2	121.7 (2)
C7—C6—H6	119.1
C7—C2—C3—C4	1.0 (4)	C1—N1—N2—N3	−0.1 (4)
N4—C2—C3—C4	180.0 (2)	N1—N2—N3—N4	−0.6 (4)
C2—C3—C4—C5	0.7 (4)	N1—C1—N4—N3	−1.2 (3)
C3—C4—C5—C6	−1.4 (4)	N1—C1—N4—C2	180.0 (3)
C3—C4—C5—C8	179.3 (3)	N2—N3—N4—C1	1.1 (3)
C4—C5—C6—C7	0.3 (4)	N2—N3—N4—C2	−180.0 (2)
C8—C5—C6—C7	179.7 (3)	C3—C2—N4—C1	157.9 (3)
C3—C2—C7—C6	−2.0 (4)	C7—C2—N4—C1	−23.2 (4)
N4—C2—C7—C6	179.0 (2)	C3—C2—N4—N3	−20.7 (4)
C5—C6—C7—C2	1.3 (4)	C7—C2—N4—N3	158.2 (2)
N4—C1—N1—N2	0.9 (3)

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgi	0.93	2.89	3.630 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgi	0.93	2.89	3.630 (3)	138

Symmetry code: (i) .