1-Chloro-1H-1,2,3-benzotriazole.

The title compound, C6H4ClN3, is essentially planar, with a maximum deviation of 0.007 (3) Å. In the crystal, a short contact of 2.818 (3) Å is observed between N and Cl atoms of adjacent mol-ecules.

Related literature

For related structures of benzotriazole derivatives, see: Jebas et al. (2012 ▶); Guo et al. (2012 ▶); Selvarathy et al. (2012 ▶); Xu & Shen (2012 ▶). For applications of the title compound, see: Hunter et al. (2006 ▶) and references cited therein. For the biological activity of benzotriazole derivatives, see: Gaikwad et al. (2012 ▶); Dubey et al. (2011 ▶).

Experimental

Crystal data

C6H4ClN3

M = 153.57

Orthorhombic,

a = 22.8022 (11) Å

b = 14.2637 (8) Å

c = 8.2259 (4) Å

V = 2675.4 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.42 × 0.34 × 0.32 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.979, T max = 1.000

1503 measured reflections

918 independent reflections

867 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.060

S = 1.06

918 reflections

91 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 275 Friedel pairs

Flack parameter: 0.00 (8)

Data collection: CrysAlis PRO (Agilent, 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044820/xu5634sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044820/xu5634Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044820/xu5634Isup3.cml

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

C6H4ClN3	Dx = 1.525 Mg m−3
Mr = 153.57	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 738 reflections
a = 22.8022 (11) Å	θ = 3.0–28.5°
b = 14.2637 (8) Å	µ = 0.48 mm−1
c = 8.2259 (4) Å	T = 293 K
V = 2675.4 (2) Å3	Block, colourless
Z = 16	0.42 × 0.34 × 0.32 mm
F(000) = 1248

Agilent Xcalibur Eos diffractometer	918 independent reflections
Radiation source: fine-focus sealed tube	867 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 16.0874 pixels mm-1	θmax = 25.2°, θmin = 3.0°
ω scans	h = −15→27
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→8
Tmin = 0.979, Tmax = 1.000	l = −9→9
1503 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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0242P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
918 reflections	Δρmax = 0.15 e Å−3
91 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 275 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (8)

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
Cl	0.31785 (3)	0.13250 (5)	−0.13509 (9)	0.0508 (2)
N1	0.37734 (9)	0.18891 (16)	−0.0618 (3)	0.0436 (6)
N2	0.43133 (10)	0.15132 (19)	−0.0788 (3)	0.0544 (7)
N3	0.46849 (10)	0.20933 (18)	−0.0121 (4)	0.0537 (7)
C1	0.37873 (11)	0.27246 (19)	0.0179 (3)	0.0369 (6)
C2	0.43801 (11)	0.2849 (2)	0.0484 (3)	0.0402 (7)
C3	0.45739 (14)	0.3651 (2)	0.1311 (4)	0.0538 (8)
H3	0.4969	0.3751	0.1531	0.065*
C4	0.41526 (15)	0.4282 (2)	0.1780 (4)	0.0577 (9)
H4	0.4265	0.4822	0.2330	0.069*
C5	0.35617 (14)	0.4133 (2)	0.1453 (4)	0.0550 (8)
H5	0.3292	0.4581	0.1796	0.066*
C6	0.33580 (13)	0.3357 (2)	0.0649 (4)	0.0459 (8)
H6	0.2962	0.3262	0.0435	0.055*

	U11	U22	U33	U12	U13	U23
Cl	0.0413 (4)	0.0522 (4)	0.0587 (4)	−0.0073 (4)	−0.0014 (4)	−0.0109 (4)
N1	0.0307 (12)	0.0452 (15)	0.0549 (15)	−0.0005 (12)	−0.0016 (12)	−0.0116 (13)
N2	0.0396 (15)	0.0519 (17)	0.072 (2)	0.0078 (12)	0.0062 (13)	−0.0114 (15)
N3	0.0327 (12)	0.0566 (16)	0.0719 (16)	0.0032 (14)	−0.0019 (13)	−0.0092 (13)
C1	0.0367 (15)	0.0383 (16)	0.0358 (14)	0.0036 (14)	−0.0016 (12)	0.0000 (13)
C2	0.0368 (15)	0.0404 (16)	0.0434 (14)	−0.0002 (13)	−0.0010 (14)	0.0022 (13)
C3	0.0494 (18)	0.057 (2)	0.0545 (19)	−0.0129 (16)	−0.010 (2)	−0.0014 (17)
C4	0.079 (2)	0.0376 (18)	0.0566 (19)	−0.0060 (18)	−0.002 (2)	−0.0069 (15)
C5	0.0570 (19)	0.0439 (19)	0.064 (2)	0.0099 (16)	0.0071 (18)	−0.0067 (18)
C6	0.0385 (15)	0.0440 (19)	0.0551 (18)	0.0071 (14)	−0.0006 (14)	−0.0004 (16)

Cl—N1	1.688 (2)	C3—C4	1.371 (4)
N1—N2	1.350 (3)	C3—H3	0.9300
N1—C1	1.360 (3)	C4—C5	1.390 (4)
N2—N3	1.305 (3)	C4—H4	0.9300
N3—C2	1.376 (4)	C5—C6	1.371 (4)
C1—C2	1.386 (3)	C5—H5	0.9300
C1—C6	1.386 (4)	C6—H6	0.9300
C2—C3	1.403 (4)
N2—N1—C1	112.1 (2)	C4—C3—H3	121.6
N2—N1—Cl	120.4 (2)	C2—C3—H3	121.6
C1—N1—Cl	127.46 (18)	C3—C4—C5	121.6 (3)
N3—N2—N1	107.3 (2)	C3—C4—H4	119.2
N2—N3—C2	108.7 (2)	C5—C4—H4	119.2
N1—C1—C2	102.8 (2)	C6—C5—C4	123.0 (3)
N1—C1—C6	133.5 (3)	C6—C5—H5	118.5
C2—C1—C6	123.7 (3)	C4—C5—H5	118.5
N3—C2—C1	109.1 (3)	C5—C6—C1	114.9 (3)
N3—C2—C3	131.0 (3)	C5—C6—H6	122.5
C1—C2—C3	120.0 (3)	C1—C6—H6	122.5
C4—C3—C2	116.8 (3)