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

There are two independent mol-ecules in the asymmetric unit of the title compound, C(7)H(5)ClN(4), in which the tetra-zole and benzene rings are twisted by dihedral angles of 12.9 (1) and 39.8 (1)°. In the crystal, the independent mol-ecules are connected into a tetra-mer by C-H⋯N hydrogen bonds, generating an R(4) (4)(12) graph-set motif.

Related literature

For applications of tetra­zoles in medicinal and synthetic chemistry, see: Butler (1996 ▶). For related structures, see: Baek et al. (2012 ▶); Matsunaga et al. (1999 ▶); Lyakhov et al. (2000 ▶, 2001 ▶). For the synthesis, see: Aridoss & Laali (2011 ▶).

Experimental

Crystal data

C7H5ClN4

M = 180.60

Monoclinic,

a = 3.8626 (2) Å

b = 27.9946 (10) Å

c = 14.4943 (5) Å

β = 95.640 (3)°

V = 1559.71 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.795, T max = 0.917

16702 measured reflections

3366 independent reflections

2610 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.101

S = 1.07

3366 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536812014353/is5104sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014353/is5104Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014353/is5104Isup3.cml

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

C7H5ClN4	F(000) = 736
Mr = 180.60	Dx = 1.538 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7146 reflections
a = 3.8626 (2) Å	θ = 3.6–29.0°
b = 27.9946 (10) Å	µ = 0.43 mm−1
c = 14.4943 (5) Å	T = 293 K
β = 95.640 (3)°	Block, white
V = 1559.71 (11) Å3	0.3 × 0.2 × 0.2 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3366 independent reflections
Radiation source: fine-focus sealed tube	2610 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 16.1049 pixels mm-1	θmax = 27.0°, θmin = 3.6°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −35→35
Tmin = 0.795, Tmax = 0.917	l = −18→18
16702 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.030P)2 + 0.7614P] where P = (Fo2 + 2Fc2)/3
3366 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 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
C1A	0.6813 (6)	0.49499 (9)	0.21942 (16)	0.0471 (6)
H1A	0.7806	0.4769	0.1750	0.057*
C2A	0.8047 (5)	0.44145 (7)	0.35903 (15)	0.0334 (5)
C3A	0.8223 (6)	0.44243 (8)	0.45455 (15)	0.0406 (5)
H3A	0.7443	0.4691	0.4848	0.049*
C4A	0.9559 (6)	0.40373 (8)	0.50482 (16)	0.0420 (5)
H4A	0.9670	0.4040	0.5692	0.050*
C5A	1.0728 (5)	0.36472 (8)	0.45945 (15)	0.0373 (5)
C6A	1.0536 (6)	0.36342 (8)	0.36386 (16)	0.0434 (5)
H6A	1.1318	0.3368	0.3338	0.052*
C7A	0.9169 (6)	0.40214 (8)	0.31318 (15)	0.0424 (5)
H7A	0.9010	0.4016	0.2487	0.051*
N1A	0.5321 (6)	0.53656 (7)	0.20473 (15)	0.0525 (5)
N2A	0.4223 (6)	0.54976 (7)	0.28770 (15)	0.0561 (6)
N3A	0.5037 (6)	0.51752 (7)	0.34968 (14)	0.0523 (5)
N4A	0.6693 (4)	0.48236 (6)	0.30800 (12)	0.0368 (4)
Cl1	1.24583 (17)	0.31657 (2)	0.52393 (4)	0.05170 (18)
C1B	0.9963 (7)	0.92383 (9)	0.51988 (17)	0.0507 (6)
H1B	1.1251	0.9410	0.5663	0.061*
C2B	1.0545 (6)	0.84159 (8)	0.58921 (15)	0.0378 (5)
C3B	1.1628 (6)	0.79776 (9)	0.56058 (17)	0.0481 (6)
H3B	1.1582	0.7909	0.4977	0.058*
C4B	1.2783 (6)	0.76411 (9)	0.62583 (18)	0.0493 (6)
H4B	1.3517	0.7343	0.6073	0.059*
C5B	1.2846 (6)	0.77494 (8)	0.71897 (16)	0.0410 (5)
C6B	1.1770 (6)	0.81872 (8)	0.74729 (16)	0.0465 (6)
H6B	1.1841	0.8257	0.8102	0.056*
C7B	1.0581 (6)	0.85244 (8)	0.68223 (16)	0.0429 (5)
H7B	0.9814	0.8821	0.7008	0.052*
N1B	0.8456 (6)	0.94204 (9)	0.44305 (16)	0.0615 (6)
N2B	0.6892 (6)	0.90440 (10)	0.39623 (15)	0.0644 (6)
N3B	0.7429 (6)	0.86506 (9)	0.44239 (15)	0.0578 (6)
N4B	0.9373 (5)	0.87688 (7)	0.52159 (12)	0.0418 (5)
Cl2	1.43462 (19)	0.73209 (2)	0.80028 (5)	0.0613 (2)

	U11	U22	U33	U12	U13	U23
C1A	0.0595 (15)	0.0454 (14)	0.0359 (13)	0.0024 (12)	0.0023 (11)	−0.0014 (11)
C2A	0.0320 (11)	0.0354 (11)	0.0327 (12)	−0.0031 (9)	0.0031 (8)	−0.0017 (9)
C3A	0.0485 (14)	0.0385 (12)	0.0355 (13)	0.0007 (10)	0.0082 (10)	−0.0075 (10)
C4A	0.0502 (14)	0.0453 (13)	0.0305 (12)	−0.0030 (11)	0.0048 (10)	−0.0025 (10)
C5A	0.0346 (11)	0.0389 (12)	0.0384 (12)	−0.0026 (9)	0.0028 (9)	0.0003 (10)
C6A	0.0500 (14)	0.0402 (12)	0.0406 (13)	0.0049 (10)	0.0080 (10)	−0.0065 (11)
C7A	0.0512 (14)	0.0474 (13)	0.0290 (12)	0.0029 (11)	0.0059 (10)	−0.0050 (10)
N1A	0.0636 (14)	0.0467 (12)	0.0455 (13)	0.0026 (10)	−0.0029 (10)	0.0016 (10)
N2A	0.0685 (15)	0.0482 (12)	0.0507 (14)	0.0092 (11)	0.0021 (11)	0.0003 (11)
N3A	0.0667 (14)	0.0457 (12)	0.0454 (13)	0.0135 (10)	0.0098 (10)	−0.0020 (10)
N4A	0.0395 (10)	0.0353 (10)	0.0354 (10)	−0.0021 (8)	0.0030 (8)	−0.0035 (8)
Cl1	0.0571 (4)	0.0493 (3)	0.0477 (4)	0.0085 (3)	0.0000 (3)	0.0054 (3)
C1B	0.0543 (15)	0.0572 (16)	0.0404 (14)	−0.0027 (12)	0.0032 (11)	0.0054 (12)
C2B	0.0355 (11)	0.0440 (12)	0.0341 (12)	−0.0057 (10)	0.0050 (9)	−0.0016 (10)
C3B	0.0568 (15)	0.0546 (15)	0.0341 (13)	−0.0037 (12)	0.0101 (11)	−0.0107 (12)
C4B	0.0551 (15)	0.0434 (13)	0.0504 (16)	0.0031 (11)	0.0100 (12)	−0.0081 (12)
C5B	0.0358 (12)	0.0426 (12)	0.0442 (14)	−0.0030 (10)	0.0027 (10)	0.0035 (11)
C6B	0.0565 (15)	0.0508 (14)	0.0320 (12)	0.0020 (12)	0.0033 (10)	−0.0053 (11)
C7B	0.0506 (14)	0.0416 (12)	0.0369 (13)	0.0048 (11)	0.0059 (10)	−0.0060 (10)
N1B	0.0652 (15)	0.0721 (15)	0.0469 (14)	0.0012 (12)	0.0039 (11)	0.0161 (12)
N2B	0.0654 (15)	0.0881 (18)	0.0385 (12)	0.0015 (14)	−0.0006 (11)	0.0108 (13)
N3B	0.0596 (14)	0.0760 (16)	0.0356 (12)	−0.0056 (12)	−0.0065 (10)	−0.0005 (11)
N4B	0.0410 (11)	0.0525 (12)	0.0316 (11)	−0.0038 (9)	0.0027 (8)	0.0008 (9)
Cl2	0.0659 (4)	0.0552 (4)	0.0607 (4)	0.0056 (3)	−0.0037 (3)	0.0109 (3)

C1A—N1A	1.307 (3)	C1B—N1B	1.308 (3)
C1A—N4A	1.337 (3)	C1B—N4B	1.335 (3)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C7A	1.377 (3)	C2B—C3B	1.374 (3)
C2A—C3A	1.380 (3)	C2B—C7B	1.381 (3)
C2A—N4A	1.434 (3)	C2B—N4B	1.433 (3)
C3A—C4A	1.378 (3)	C3B—C4B	1.378 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.374 (3)	C4B—C5B	1.381 (3)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.381 (3)	C5B—C6B	1.370 (3)
C5A—Cl1	1.736 (2)	C5B—Cl2	1.741 (2)
C6A—C7A	1.385 (3)	C6B—C7B	1.381 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—H7A	0.9300	C7B—H7B	0.9300
N1A—N2A	1.365 (3)	N1B—N2B	1.362 (3)
N2A—N3A	1.290 (3)	N2B—N3B	1.295 (3)
N3A—N4A	1.349 (2)	N3B—N4B	1.350 (3)
N1A—C1A—N4A	109.6 (2)	N1B—C1B—N4B	109.7 (2)
N1A—C1A—H1A	125.2	N1B—C1B—H1B	125.2
N4A—C1A—H1A	125.2	N4B—C1B—H1B	125.2
C7A—C2A—C3A	120.9 (2)	C3B—C2B—C7B	121.2 (2)
C7A—C2A—N4A	120.34 (19)	C3B—C2B—N4B	119.6 (2)
C3A—C2A—N4A	118.77 (19)	C7B—C2B—N4B	119.2 (2)
C4A—C3A—C2A	119.6 (2)	C2B—C3B—C4B	119.4 (2)
C4A—C3A—H3A	120.2	C2B—C3B—H3B	120.3
C2A—C3A—H3A	120.2	C4B—C3B—H3B	120.3
C5A—C4A—C3A	119.7 (2)	C3B—C4B—C5B	119.6 (2)
C5A—C4A—H4A	120.1	C3B—C4B—H4B	120.2
C3A—C4A—H4A	120.1	C5B—C4B—H4B	120.2
C4A—C5A—C6A	120.9 (2)	C6B—C5B—C4B	120.8 (2)
C4A—C5A—Cl1	119.12 (17)	C6B—C5B—Cl2	120.29 (19)
C6A—C5A—Cl1	119.99 (17)	C4B—C5B—Cl2	118.89 (18)
C5A—C6A—C7A	119.5 (2)	C5B—C6B—C7B	119.8 (2)
C5A—C6A—H6A	120.3	C5B—C6B—H6B	120.1
C7A—C6A—H6A	120.3	C7B—C6B—H6B	120.1
C2A—C7A—C6A	119.4 (2)	C6B—C7B—C2B	119.2 (2)
C2A—C7A—H7A	120.3	C6B—C7B—H7B	120.4
C6A—C7A—H7A	120.3	C2B—C7B—H7B	120.4
C1A—N1A—N2A	105.5 (2)	C1B—N1B—N2B	105.2 (2)
N3A—N2A—N1A	110.40 (19)	N3B—N2B—N1B	111.1 (2)
N2A—N3A—N4A	107.00 (19)	N2B—N3B—N4B	106.2 (2)
C1A—N4A—N3A	107.45 (18)	C1B—N4B—N3B	107.9 (2)
C1A—N4A—C2A	131.41 (19)	C1B—N4B—C2B	130.4 (2)
N3A—N4A—C2A	121.11 (18)	N3B—N4B—C2B	121.6 (2)
C7A—C2A—C3A—C4A	0.4 (3)	C7B—C2B—C3B—C4B	−0.3 (4)
N4A—C2A—C3A—C4A	−179.11 (19)	N4B—C2B—C3B—C4B	179.4 (2)
C2A—C3A—C4A—C5A	0.5 (3)	C2B—C3B—C4B—C5B	−0.2 (4)
C3A—C4A—C5A—C6A	−0.9 (3)	C3B—C4B—C5B—C6B	0.0 (4)
C3A—C4A—C5A—Cl1	179.15 (17)	C3B—C4B—C5B—Cl2	−179.50 (18)
C4A—C5A—C6A—C7A	0.5 (3)	C4B—C5B—C6B—C7B	0.5 (4)
Cl1—C5A—C6A—C7A	−179.63 (17)	Cl2—C5B—C6B—C7B	−179.93 (18)
C3A—C2A—C7A—C6A	−0.9 (3)	C5B—C6B—C7B—C2B	−0.9 (4)
N4A—C2A—C7A—C6A	178.63 (19)	C3B—C2B—C7B—C6B	0.8 (3)
C5A—C6A—C7A—C2A	0.5 (3)	N4B—C2B—C7B—C6B	−178.8 (2)
N4A—C1A—N1A—N2A	−0.4 (3)	N4B—C1B—N1B—N2B	−0.1 (3)
C1A—N1A—N2A—N3A	0.3 (3)	C1B—N1B—N2B—N3B	−0.1 (3)
N1A—N2A—N3A—N4A	0.0 (3)	N1B—N2B—N3B—N4B	0.3 (3)
N1A—C1A—N4A—N3A	0.4 (3)	N1B—C1B—N4B—N3B	0.3 (3)
N1A—C1A—N4A—C2A	−177.6 (2)	N1B—C1B—N4B—C2B	178.2 (2)
N2A—N3A—N4A—C1A	−0.2 (3)	N2B—N3B—N4B—C1B	−0.4 (3)
N2A—N3A—N4A—C2A	178.05 (19)	N2B—N3B—N4B—C2B	−178.4 (2)
C7A—C2A—N4A—C1A	−13.8 (3)	C3B—C2B—N4B—C1B	−138.5 (3)
C3A—C2A—N4A—C1A	165.7 (2)	C7B—C2B—N4B—C1B	41.1 (3)
C7A—C2A—N4A—N3A	168.4 (2)	C3B—C2B—N4B—N3B	39.1 (3)
C3A—C2A—N4A—N3A	−12.0 (3)	C7B—C2B—N4B—N3B	−141.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···N1Bi	0.93	2.54	3.454 (3)	167
C1B—H1B···N1Aii	0.93	2.50	3.406 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯N1Bi	0.93	2.54	3.454 (3)	167
C1B—H1B⋯N1Aii	0.93	2.50	3.406 (3)	163

Symmetry codes: (i) ; (ii) .