1-(3,5-Dichloro-phen-yl)-1H-1,2,3,4-tetra-zole.

In the title compound, C(7)H(4)Cl(2)N(4), the dihedral angle between the tetra-zole and benzene rings is 17.2 (2)°. In the crystal, C-H⋯N inter-actions link the mol-ecules into a flattened helical chain along the b axis.

Related literature

For related structures, see: Baek et al. (2012 ▶); Matsunaga et al. (1999 ▶); Lyakhov et al. (2000 ▶, 2001 ▶). For the synthesis, see: Su et al. (2006 ▶).

Experimental

Crystal data

C7H4Cl2N4

M = 215.04

Monoclinic,

a = 3.8362 (2) Å

b = 9.0524 (3) Å

c = 24.8876 (11) Å

β = 91.956 (4)°

V = 863.76 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.70 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 = 0.699, T max = 0.869

16772 measured reflections

1692 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.114

S = 1.17

1692 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.25 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001225/is5049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001225/is5049Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001225/is5049Isup3.cml

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

C7H4Cl2N4	F(000) = 432
Mr = 215.04	Dx = 1.654 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7140 reflections
a = 3.8362 (2) Å	θ = 4.0–29.0°
b = 9.0524 (3) Å	µ = 0.70 mm−1
c = 24.8876 (11) Å	T = 293 K
β = 91.956 (4)°	Block, white
V = 863.76 (7) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1692 independent reflections
Radiation source: fine-focus sealed tube	1451 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 4.0°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.699, Tmax = 0.869	l = −30→30
16772 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0229P)2 + 1.3257P] where P = (Fo2 + 2Fc2)/3
1692 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.24 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	0.8151 (11)	0.8952 (4)	0.22313 (15)	0.0569 (10)
H1	0.7634	0.8155	0.2450	0.068*
C2	0.5993 (8)	0.7942 (3)	0.13392 (12)	0.0332 (7)
C3	0.4810 (8)	0.8412 (4)	0.08358 (13)	0.0389 (7)
H3	0.4966	0.9397	0.0734	0.047*
C4	0.3391 (8)	0.7360 (4)	0.04919 (12)	0.0410 (8)
C5	0.3089 (8)	0.5895 (4)	0.06386 (13)	0.0405 (8)
H5	0.2125	0.5202	0.0401	0.049*
C6	0.4258 (8)	0.5491 (3)	0.11477 (13)	0.0378 (7)
C7	0.5739 (8)	0.6494 (3)	0.15071 (12)	0.0348 (7)
H7	0.6533	0.6204	0.1848	0.042*
N1	0.9600 (10)	1.0175 (4)	0.23973 (13)	0.0619 (9)
N2	0.9905 (10)	1.1003 (4)	0.19516 (15)	0.0682 (10)
N3	0.8690 (10)	1.0311 (3)	0.15319 (13)	0.0655 (10)
N4	0.7517 (7)	0.9004 (3)	0.17044 (11)	0.0379 (6)
Cl1	0.1904 (3)	0.78829 (13)	−0.01453 (4)	0.0645 (3)
Cl2	0.3786 (3)	0.36798 (10)	0.13489 (4)	0.0639 (3)

	U11	U22	U33	U12	U13	U23
C1	0.084 (3)	0.043 (2)	0.042 (2)	−0.014 (2)	−0.0130 (19)	0.0013 (16)
C2	0.0334 (16)	0.0344 (16)	0.0319 (16)	−0.0010 (13)	0.0023 (12)	−0.0025 (13)
C3	0.0421 (18)	0.0371 (18)	0.0375 (17)	−0.0027 (14)	−0.0005 (14)	0.0056 (14)
C4	0.0377 (17)	0.054 (2)	0.0309 (16)	−0.0017 (15)	−0.0021 (13)	0.0045 (15)
C5	0.0388 (18)	0.0460 (19)	0.0367 (17)	−0.0075 (15)	−0.0016 (14)	−0.0061 (15)
C6	0.0403 (17)	0.0319 (16)	0.0414 (18)	−0.0016 (14)	0.0022 (14)	−0.0008 (14)
C7	0.0375 (17)	0.0351 (17)	0.0317 (16)	−0.0022 (13)	−0.0007 (13)	0.0018 (13)
N1	0.087 (3)	0.0454 (18)	0.052 (2)	−0.0120 (18)	−0.0179 (17)	−0.0070 (15)
N2	0.096 (3)	0.0420 (18)	0.065 (2)	−0.0217 (18)	−0.015 (2)	−0.0050 (17)
N3	0.103 (3)	0.0397 (17)	0.053 (2)	−0.0251 (18)	−0.0099 (19)	0.0065 (15)
N4	0.0451 (15)	0.0307 (14)	0.0375 (14)	−0.0040 (12)	−0.0038 (12)	−0.0002 (11)
Cl1	0.0754 (7)	0.0796 (7)	0.0374 (5)	−0.0070 (6)	−0.0160 (4)	0.0084 (5)
Cl2	0.0968 (8)	0.0353 (5)	0.0589 (6)	−0.0147 (5)	−0.0059 (5)	0.0006 (4)

C1—N1	1.300 (5)	C4—Cl1	1.733 (3)
C1—N4	1.326 (4)	C5—C6	1.379 (4)
C1—H1	0.9300	C5—H5	0.9300
C2—C7	1.381 (4)	C6—C7	1.383 (4)
C2—C3	1.384 (4)	C6—Cl2	1.726 (3)
C2—N4	1.434 (4)	C7—H7	0.9300
C3—C4	1.380 (4)	N1—N2	1.347 (5)
C3—H3	0.9300	N2—N3	1.291 (4)
C4—C5	1.382 (5)	N3—N4	1.342 (4)
N1—C1—N4	110.3 (3)	C4—C5—H5	121.0
N1—C1—H1	124.9	C5—C6—C7	122.3 (3)
N4—C1—H1	124.9	C5—C6—Cl2	119.0 (2)
C7—C2—C3	122.7 (3)	C7—C6—Cl2	118.7 (2)
C7—C2—N4	118.4 (3)	C2—C7—C6	117.3 (3)
C3—C2—N4	118.8 (3)	C2—C7—H7	121.3
C4—C3—C2	117.4 (3)	C6—C7—H7	121.3
C4—C3—H3	121.3	C1—N1—N2	105.1 (3)
C2—C3—H3	121.3	N3—N2—N1	110.9 (3)
C3—C4—C5	122.2 (3)	N2—N3—N4	106.5 (3)
C3—C4—Cl1	119.3 (3)	C1—N4—N3	107.2 (3)
C5—C4—Cl1	118.4 (3)	C1—N4—C2	131.3 (3)
C6—C5—C4	118.0 (3)	N3—N4—C2	121.5 (3)
C6—C5—H5	121.0
C7—C2—C3—C4	−1.3 (5)	N4—C1—N1—N2	−0.8 (5)
N4—C2—C3—C4	179.3 (3)	C1—N1—N2—N3	0.0 (5)
C2—C3—C4—C5	1.0 (5)	N1—N2—N3—N4	0.7 (5)
C2—C3—C4—Cl1	−179.5 (2)	N1—C1—N4—N3	1.2 (5)
C3—C4—C5—C6	0.0 (5)	N1—C1—N4—C2	179.6 (3)
Cl1—C4—C5—C6	−179.6 (2)	N2—N3—N4—C1	−1.2 (4)
C4—C5—C6—C7	−0.8 (5)	N2—N3—N4—C2	−179.7 (3)
C4—C5—C6—Cl2	178.0 (3)	C7—C2—N4—C1	−16.1 (5)
C3—C2—C7—C6	0.6 (5)	C3—C2—N4—C1	163.4 (4)
N4—C2—C7—C6	180.0 (3)	C7—C2—N4—N3	162.1 (3)
C5—C6—C7—C2	0.5 (5)	C3—C2—N4—N3	−18.4 (5)
Cl2—C6—C7—C2	−178.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2i	0.93	2.61	3.423 (5)	147
C7—H7···N1i	0.93	2.53	3.424 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2i	0.93	2.61	3.423 (5)	147
C7—H7⋯N1i	0.93	2.53	3.424 (5)	161

Symmetry code: (i) .