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

In the title compound, C(7)H(6)ClN(3), the benzotriazole ring is essentially planar with a maximum deviation of 0.0110 (15)Å, and makes a dihedral angle of 0.46 (8)° with the benzene ring. In the crystal, mol-ecules are linked through inter-molecular C-H⋯N hydrogen bonds, forming chains along the c axis.

Related literature

For bond-length data, see: Alkorta et al. (2004 ▶); Wang et al. (2008 ▶). For applications of 1-(chloro­meth­yl)benzotriazole, see: Katritzky et al. (1996 ▶). For the preparation of the title compound, see: Burckhalter et al. (1952 ▶). For the biological activity of benzotriazole derivatives, see: Jiao et al. (2005 ▶).

Experimental

Crystal data

C7H6ClN3

M = 167.60

Monoclinic,

a = 7.5081 (17) Å

b = 9.6045 (14) Å

c = 10.984 (2) Å

β = 108.49 (2)°

V = 751.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.21 × 0.20 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.914, T max = 0.922

2865 measured reflections

1530 independent reflections

1218 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.06

1530 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); data reduction: CrysAlis RED; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046052/fl2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046052/fl2325Isup2.hkl

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

C7H6ClN3	F(000) = 344
Mr = 167.60	Dx = 1.482 Mg m−3
Monoclinic, P21/c	Melting point: 409.5 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.7107 Å
a = 7.5081 (17) Å	Cell parameters from 1327 reflections
b = 9.6045 (14) Å	θ = 3.6–26.4°
c = 10.984 (2) Å	µ = 0.44 mm−1
β = 108.49 (2)°	T = 293 K
V = 751.2 (3) Å3	Block, colourless
Z = 4	0.21 × 0.20 × 0.19 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	1218 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.016
graphite	θmax = 26.4°, θmin = 3.6°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −12→9
Tmin = 0.914, Tmax = 0.922	l = −8→13
2865 measured reflections	2865 standard reflections every 0 min
1530 independent reflections	intensity decay: none

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.0967P] where P = (Fo2 + 2Fc2)/3
1530 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.16 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
Cl1	0.28373 (7)	0.06214 (5)	0.48763 (5)	0.0569 (2)
N1	0.12629 (19)	0.31134 (15)	0.42214 (12)	0.0387 (3)
C6	0.2688 (2)	0.44038 (19)	0.63087 (16)	0.0411 (4)
H6A	0.2580	0.3716	0.6877	0.049*
N2	0.0960 (2)	0.34462 (18)	0.29614 (13)	0.0509 (4)
C7	0.0840 (2)	0.17530 (18)	0.45677 (18)	0.0436 (4)
H7A	−0.0195	0.1369	0.3878	0.052*
H7B	0.0453	0.1810	0.5329	0.052*
N3	0.1527 (2)	0.47155 (18)	0.29024 (14)	0.0534 (4)
C2	0.2235 (2)	0.52323 (19)	0.41342 (16)	0.0403 (4)
C1	0.2084 (2)	0.42052 (17)	0.49813 (15)	0.0332 (4)
C4	0.3611 (3)	0.6730 (2)	0.5873 (2)	0.0557 (5)
H4A	0.4140	0.7581	0.6204	0.067*
C3	0.3011 (3)	0.6533 (2)	0.4584 (2)	0.0514 (5)
H3B	0.3111	0.7231	0.4023	0.062*
C5	0.3451 (3)	0.5681 (2)	0.67153 (19)	0.0504 (5)
H5A	0.3884	0.5860	0.7592	0.061*

	U11	U22	U33	U12	U13	U23
Cl1	0.0606 (3)	0.0432 (3)	0.0670 (4)	0.0114 (2)	0.0204 (3)	0.0072 (2)
N1	0.0447 (8)	0.0379 (8)	0.0319 (7)	0.0053 (6)	0.0098 (6)	0.0008 (6)
C6	0.0460 (10)	0.0417 (10)	0.0365 (9)	0.0045 (8)	0.0142 (8)	0.0023 (8)
N2	0.0602 (10)	0.0574 (11)	0.0318 (8)	0.0121 (8)	0.0099 (7)	0.0023 (7)
C7	0.0432 (10)	0.0380 (10)	0.0489 (10)	0.0000 (8)	0.0135 (8)	−0.0045 (8)
N3	0.0648 (11)	0.0583 (11)	0.0393 (8)	0.0149 (9)	0.0198 (8)	0.0126 (8)
C2	0.0421 (10)	0.0433 (10)	0.0390 (9)	0.0114 (8)	0.0178 (8)	0.0094 (8)
C1	0.0325 (8)	0.0337 (9)	0.0348 (9)	0.0063 (7)	0.0125 (7)	0.0021 (7)
C4	0.0531 (12)	0.0403 (11)	0.0729 (13)	−0.0051 (9)	0.0188 (10)	−0.0092 (11)
C3	0.0534 (12)	0.0393 (11)	0.0682 (13)	0.0027 (9)	0.0286 (10)	0.0137 (10)
C5	0.0539 (11)	0.0513 (12)	0.0432 (10)	0.0019 (9)	0.0114 (9)	−0.0100 (9)

Cl1—C7	1.7950 (18)	C7—H7B	0.9700
N1—C1	1.360 (2)	N3—C2	1.380 (2)
N1—N2	1.3674 (19)	C2—C1	1.385 (2)
N1—C7	1.424 (2)	C2—C3	1.401 (3)
C6—C5	1.367 (3)	C4—C3	1.356 (3)
C6—C1	1.396 (2)	C4—C5	1.399 (3)
C6—H6A	0.9300	C4—H4A	0.9300
N2—N3	1.299 (2)	C3—H3B	0.9300
C7—H7A	0.9700	C5—H5A	0.9300
C1—N1—N2	109.78 (14)	N3—C2—C3	130.89 (17)
C1—N1—C7	129.74 (13)	C1—C2—C3	120.79 (16)
N2—N1—C7	120.34 (14)	N1—C1—C2	104.75 (14)
C5—C6—C1	115.31 (17)	N1—C1—C6	132.87 (15)
C5—C6—H6A	122.3	C2—C1—C6	122.38 (16)
C1—C6—H6A	122.3	C3—C4—C5	121.34 (18)
N3—N2—N1	108.53 (14)	C3—C4—H4A	119.3
N1—C7—Cl1	111.25 (12)	C5—C4—H4A	119.3
N1—C7—H7A	109.4	C4—C3—C2	117.14 (17)
Cl1—C7—H7A	109.4	C4—C3—H3B	121.4
N1—C7—H7B	109.4	C2—C3—H3B	121.4
Cl1—C7—H7B	109.4	C6—C5—C4	123.04 (18)
H7A—C7—H7B	108.0	C6—C5—H5A	118.5
N2—N3—C2	108.61 (14)	C4—C5—H5A	118.5
N3—C2—C1	108.32 (16)
C1—N1—N2—N3	−1.26 (19)	N3—C2—C1—N1	−0.84 (18)
C7—N1—N2—N3	−177.32 (15)	C3—C2—C1—N1	179.33 (15)
C1—N1—C7—Cl1	−84.43 (19)	N3—C2—C1—C6	179.77 (15)
N2—N1—C7—Cl1	90.74 (16)	C3—C2—C1—C6	−0.1 (3)
N1—N2—N3—C2	0.7 (2)	C5—C6—C1—N1	−179.59 (17)
N2—N3—C2—C1	0.1 (2)	C5—C6—C1—C2	−0.4 (2)
N2—N3—C2—C3	179.91 (18)	C5—C4—C3—C2	−0.3 (3)
N2—N1—C1—C2	1.27 (18)	N3—C2—C3—C4	−179.37 (18)
C7—N1—C1—C2	176.84 (16)	C1—C2—C3—C4	0.4 (3)
N2—N1—C1—C6	−179.43 (17)	C1—C6—C5—C4	0.5 (3)
C7—N1—C1—C6	−3.9 (3)	C3—C4—C5—C6	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N3i	0.97	2.47	3.360 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N3i	0.97	2.47	3.360 (2)	152

Symmetry code: (i) .