5-(4-Chloro-benz-yl)-1H-tetra-zole.

In the title compound, C(8)H(7)ClN(4), the phenyl and tetra-zole rings are inclined at a dihedral angle of 67.52 (6)°. In the crystal, mol-ecules are linked by an N-H⋯N hydrogen bond into a chain structure along [010]. π-π inter-actions with centroid-centroid distances of 3.526 (1) Å between adjacent tetra-zole rings further link the chains, forming a ribbon structure.

Related literature

For background to tetra­zole compounds, see: Kitagawa et al. (2004 ▶); Zhao et al. (2008 ▶); For the synthesis, see: Luo et al. (2006 ▶).

Experimental

Crystal data

C8H7ClN4

M = 194.63

Monoclinic,

a = 14.654 (3) Å

b = 4.9321 (10) Å

c = 12.688 (3) Å

β = 105.63 (3)°

V = 883.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.40 × 0.38 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.860, T max = 0.944

8039 measured reflections

2015 independent reflections

1546 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.08

2015 reflections

122 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.33 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002) ▶; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028388/ng5199sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028388/ng5199Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028388/ng5199Isup3.cml

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

C8H7ClN4	F(000) = 400
Mr = 194.63	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6142 reflections
a = 14.654 (3) Å	θ = 3.3–25.1°
b = 4.9321 (10) Å	µ = 0.39 mm−1
c = 12.688 (3) Å	T = 293 K
β = 105.63 (3)°	Block, colorless
V = 883.1 (3) Å3	0.40 × 0.38 × 0.15 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2015 independent reflections
Radiation source: fine-focus sealed tube	1546 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −18→19
Tmin = 0.860, Tmax = 0.944	k = −6→6
8039 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0994P] where P = (Fo2 + 2Fc2)/3
2015 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.33 e Å−3

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 > 2sigma(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	0.37038 (9)	0.2990 (3)	1.07319 (14)	0.0463 (4)
C2	0.29853 (11)	0.4022 (3)	1.11205 (14)	0.0503 (4)
H2	0.2911	0.3450	1.1791	0.060*
C3	0.23731 (10)	0.5923 (3)	1.05032 (13)	0.0465 (4)
H3	0.1891	0.6638	1.0768	0.056*
C4	0.24675 (9)	0.6773 (3)	0.95005 (12)	0.0380 (3)
C5	0.31899 (11)	0.5667 (3)	0.91227 (15)	0.0467 (4)
H5	0.3259	0.6203	0.8446	0.056*
C6	0.38090 (11)	0.3781 (3)	0.97347 (15)	0.0518 (4)
H6	0.4292	0.3057	0.9473	0.062*
C7	0.18309 (10)	0.8938 (3)	0.88444 (14)	0.0451 (4)
H7A	0.2059	1.0694	0.9149	0.054*
H7B	0.1887	0.8888	0.8100	0.054*
C8	0.08089 (9)	0.8704 (2)	0.88086 (11)	0.0311 (3)
Cl1	0.44739 (3)	0.06175 (9)	1.15206 (5)	0.0707 (2)
N1	0.03034 (8)	0.6471 (2)	0.87394 (9)	0.0347 (3)
N2	−0.06056 (8)	0.7269 (2)	0.86416 (10)	0.0393 (3)
N3	−0.06566 (8)	0.9885 (2)	0.86545 (10)	0.0404 (3)
N4	0.02296 (8)	1.0797 (2)	0.87674 (9)	0.0346 (3)
H1	0.0343 (11)	1.2592 (6)	0.8810 (12)	0.048 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0327 (7)	0.0365 (7)	0.0624 (10)	0.0041 (6)	0.0001 (6)	−0.0060 (7)
C2	0.0506 (9)	0.0497 (9)	0.0504 (10)	0.0101 (7)	0.0130 (7)	0.0055 (7)
C3	0.0416 (8)	0.0477 (9)	0.0531 (10)	0.0127 (7)	0.0176 (7)	0.0025 (7)
C4	0.0330 (6)	0.0302 (7)	0.0494 (9)	−0.0047 (6)	0.0090 (6)	−0.0018 (6)
C5	0.0424 (8)	0.0469 (9)	0.0548 (10)	−0.0032 (7)	0.0198 (7)	−0.0019 (7)
C6	0.0354 (7)	0.0486 (9)	0.0741 (12)	0.0022 (7)	0.0194 (8)	−0.0124 (8)
C7	0.0401 (7)	0.0327 (7)	0.0615 (10)	−0.0044 (6)	0.0119 (7)	0.0091 (7)
C8	0.0390 (6)	0.0224 (6)	0.0306 (7)	0.0005 (5)	0.0068 (5)	0.0001 (5)
Cl1	0.0512 (3)	0.0538 (3)	0.0907 (4)	0.0194 (2)	−0.0094 (2)	−0.0025 (2)
N1	0.0390 (6)	0.0229 (5)	0.0424 (7)	−0.0012 (5)	0.0115 (5)	−0.0019 (4)
N2	0.0390 (6)	0.0329 (6)	0.0473 (7)	−0.0002 (5)	0.0140 (5)	−0.0006 (5)
N3	0.0429 (6)	0.0337 (6)	0.0465 (7)	0.0059 (5)	0.0153 (5)	0.0025 (5)
N4	0.0461 (6)	0.0209 (5)	0.0366 (7)	0.0024 (5)	0.0107 (5)	0.0003 (4)

C1—C6	1.372 (2)	C6—H6	0.9300
C1—C2	1.375 (2)	C7—C8	1.4906 (19)
C1—Cl1	1.7423 (16)	C7—H7A	0.9700
C2—C3	1.385 (2)	C7—H7B	0.9700
C2—H2	0.9300	C8—N1	1.3169 (17)
C3—C4	1.381 (2)	C8—N4	1.3284 (17)
C3—H3	0.9300	N1—N2	1.3622 (16)
C4—C5	1.386 (2)	N2—N3	1.2927 (17)
C4—C7	1.5117 (19)	N3—N4	1.3449 (17)
C5—C6	1.383 (2)	N4—H1	0.8998 (11)
C5—H5	0.9300
C6—C1—C2	120.83 (14)	C5—C6—H6	120.3
C6—C1—Cl1	120.30 (12)	C8—C7—C4	115.34 (12)
C2—C1—Cl1	118.87 (14)	C8—C7—H7A	108.4
C1—C2—C3	119.32 (16)	C4—C7—H7A	108.4
C1—C2—H2	120.3	C8—C7—H7B	108.4
C3—C2—H2	120.3	C4—C7—H7B	108.4
C4—C3—C2	121.06 (13)	H7A—C7—H7B	107.5
C4—C3—H3	119.5	N1—C8—N4	107.77 (11)
C2—C3—H3	119.5	N1—C8—C7	127.54 (12)
C3—C4—C5	118.32 (14)	N4—C8—C7	124.55 (12)
C3—C4—C7	121.43 (13)	C8—N1—N2	106.44 (10)
C5—C4—C7	120.20 (14)	N3—N2—N1	110.23 (11)
C6—C5—C4	121.15 (16)	N2—N3—N4	106.11 (11)
C6—C5—H5	119.4	C8—N4—N3	109.45 (11)
C4—C5—H5	119.4	C8—N4—H1	131.0 (11)
C1—C6—C5	119.31 (14)	N3—N4—H1	119.5 (10)
C1—C6—H6	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1···N1i	0.90 (1)	1.92 (1)	2.8013 (15)	168.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1⋯N1i	0.90 (1)	1.92 (1)	2.8013 (15)	168 (2)

Symmetry code: (i) .