5-p-Tolyl-1H-tetra-zole.

The title compound, C(8)H(8)N(4), possesses crystallographic mirror symmetry, with four C atoms lying on the reflecting plane, which bis-ects the phenyl and tetra-zole rings. It is composed of a planar r.m.s. deviation (0.0012 Å) tetra-zole ring which is nearly coplanar with the benzene ring, the dihedral angle being 2.67 (9)°. In the crystal, symmetry-related mol-ecules are linked by inter-molecular N-H⋯N hydrogen bonds. The mol-ecules stack along [100] with a π⋯π inter-action involving the phenyl and tetra-zole rings of adjacent mol-ecules [centroid-centroid distance = 3.5639 (15) Å]. The H atom of the N-H group is disordered over two sites of equal occupancy. The methyl H atoms were modelled as disordered over two sets of sites of equal occupancy rotated by 60° with respect to each other.

Related literature

For related manganese(II) complexes, see: Hu et al. (2007 ▶); Lü (2008 ▶). For applications of tetra­zoles in coordination chemistry, medicinal chemistry and materials science, see: Xiong et al. (2002 ▶); Xue et al. (2002 ▶); Wang et al. (2005 ▶); Dunica et al. (1991 ▶); Wittenberger et al. (1993 ▶).

Experimental

Crystal data

C8H8N4

M = 160.18

Orthorhombic,

a = 4.5370 (15) Å

b = 17.729 (5) Å

c = 9.778 (2) Å

V = 786.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku, SCXmini diffractometer

Absorption correction: multi-scan CrystalClear (Rigaku, 2005 ▶) T min = 0.981, T max = 0.983

7310 measured reflections

946 independent reflections

792 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.115

S = 1.12

946 reflections

66 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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809036411/su2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036411/su2134Isup2.hkl

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

C8H8N4	F(000) = 336
Mr = 160.18	Dx = 1.353 Mg m−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 1044 reflections
a = 4.5370 (15) Å	θ = 3.0–27.4°
b = 17.729 (5) Å	µ = 0.09 mm−1
c = 9.778 (2) Å	T = 293 K
V = 786.5 (4) Å3	Block, pale yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Rigaku, SCXmini diffractometer	946 independent reflections
Radiation source: fine-focus sealed tube	792 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −5→5
Absorption correction: multi-scan CrystalClear (Rigaku, 2005)	k = −23→22
Tmin = 0.981, Tmax = 0.983	l = −12→12
7310 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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
946 reflections	Δρmax = 0.17 e Å−3
66 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (5)

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	Occ. (<1)
C1	0.2469 (4)	0.17076 (11)	0.2500	0.0386 (5)
C2	0.3511 (3)	0.14064 (8)	0.12792 (15)	0.0478 (4)
H2	0.2895	0.1610	0.0451	0.057*
C3	0.5451 (4)	0.08076 (9)	0.12874 (17)	0.0543 (5)
H3	0.6133	0.0616	0.0461	0.065*
C4	0.6408 (5)	0.04856 (12)	0.2500	0.0521 (6)
C7	0.0344 (4)	0.23258 (11)	0.2500	0.0363 (5)
C8	0.8408 (6)	−0.01930 (14)	0.2500	0.0746 (8)
H8A	0.8837	−0.0336	0.3426	0.112*	0.50
H8B	1.0209	−0.0071	0.2035	0.112*	0.50
H8C	0.7450	−0.0604	0.2039	0.112*	0.50
N1	−0.0825 (3)	0.26572 (7)	0.35937 (12)	0.0435 (4)
N2	−0.2736 (3)	0.31947 (7)	0.31588 (13)	0.0489 (4)
H1	−0.064 (6)	0.2534 (19)	0.446 (3)	0.045 (8)*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0394 (10)	0.0431 (10)	0.0333 (10)	−0.0074 (9)	0.000	0.000
C2	0.0540 (9)	0.0525 (9)	0.0369 (8)	−0.0014 (7)	0.0021 (7)	−0.0017 (6)
C3	0.0544 (9)	0.0552 (9)	0.0532 (10)	−0.0016 (8)	0.0081 (7)	−0.0105 (8)
C4	0.0428 (12)	0.0430 (12)	0.0705 (16)	−0.0079 (10)	0.000	0.000
C7	0.0415 (10)	0.0411 (10)	0.0262 (8)	−0.0109 (8)	0.000	0.000
C8	0.0601 (15)	0.0542 (15)	0.109 (2)	0.0045 (13)	0.000	0.000
N1	0.0538 (7)	0.0477 (7)	0.0291 (6)	−0.0020 (6)	0.0017 (5)	−0.0010 (5)
N2	0.0607 (8)	0.0489 (7)	0.0371 (6)	0.0011 (6)	0.0030 (6)	−0.0019 (5)

C1—C2	1.3905 (18)	C7—N1i	1.3306 (17)
C1—C2i	1.3905 (18)	C7—N1	1.3306 (17)
C1—C7	1.460 (3)	C8—H8A	0.9600
C2—C3	1.379 (2)	C8—H8B	0.9600
C2—H2	0.9300	C8—H8C	0.9600
C3—C4	1.386 (2)	N1—N2	1.3566 (17)
C3—H3	0.9300	N1—H1	0.87 (3)
C4—C3i	1.386 (2)	N2—N2i	1.288 (2)
C4—C8	1.507 (3)
C2—C1—C2i	118.28 (19)	N1i—C7—C1	126.51 (9)
C2—C1—C7	120.86 (10)	N1—C7—C1	126.51 (9)
C2i—C1—C7	120.86 (10)	C4—C8—H8A	109.5
C3—C2—C1	120.51 (15)	C4—C8—H8B	109.5
C3—C2—H2	119.7	H8A—C8—H8B	109.5
C1—C2—H2	119.7	C4—C8—H8C	109.5
C2—C3—C4	121.47 (16)	H8A—C8—H8C	109.5
C2—C3—H3	119.3	H8B—C8—H8C	109.5
C4—C3—H3	119.3	C7—N1—N2	108.24 (12)
C3i—C4—C3	117.7 (2)	C7—N1—H1	129 (2)
C3i—C4—C8	121.17 (11)	N2—N1—H1	123 (2)
C3—C4—C8	121.17 (11)	N2i—N2—N1	108.27 (7)
N1i—C7—N1	106.98 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N1ii	0.87 (3)	1.94 (3)	2.806 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N1i	0.87 (3)	1.94 (3)	2.806 (2)	171 (3)

Symmetry code: (i) .