1-Benzyl-1H-benzotriazole.

In the title compound, C(13)H(11)N(3), the benzotriazole ring system is essentially planar, with a maximum deviation of 0.0173 (18) Å, and forms a dihedral angle of 75.08 (8)Å with the phenyl ring. In the crystal, pairs of weak C-H⋯N hydrogen bonds form inversion dimers. In addition, there are weak C-H⋯π(arene) inter-actions and weak π-π stacking inter-actions, with a centroid-centroid distance of 3.673 (11) Å.

Related literature

For the biological activity of benzotriazole derivatives, see: Katarzyna et al. (2005 ▶); Sarala et al. (2007 ▶). For their applications, see: Kopec et al. (2008 ▶); Krawczyk & Gdaniec (2005 ▶); Smith et al. (2001 ▶); Sha et al. (1996 ▶). For a related structure, see: Ravindran et al. (2009 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H11N3

M = 209.25

Monoclinic,

a = 11.5734 (10) Å

b = 5.9705 (4) Å

c = 16.1202 (14) Å

β = 106.490 (4)°

V = 1068.07 (15) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 193 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶; Wiehl & Schollmeyer, 1994 ▶) T min = 0.832, T max = 0.939

2125 measured reflections

2020 independent reflections

1788 reflections with I > 2σ(I)

R int = 0.108

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.138

S = 1.12

2020 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶; Wiehl & Schollmeyer, 1994 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010951/lh5426sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010951/lh5426Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010951/lh5426Isup3.cml

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

C13H11N3	F(000) = 440
Mr = 209.25	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.5734 (10) Å	θ = 55–68°
b = 5.9705 (4) Å	µ = 0.64 mm−1
c = 16.1202 (14) Å	T = 193 K
β = 106.490 (4)°	Block, colourless
V = 1068.07 (15) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1788 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.108
Graphite monochromator	θmax = 70.0°, θmin = 4.0°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994)	k = 0→7
Tmin = 0.832, Tmax = 0.939	l = −19→18
2125 measured reflections	3 standard reflections every 60 min
2020 independent reflections	intensity decay: 2%

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.3976P] where P = (Fo2 + 2Fc2)/3
2020 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.30 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
N1	0.42315 (15)	0.1763 (3)	0.37392 (11)	0.0331 (4)
N2	0.40768 (14)	0.2958 (3)	0.30376 (10)	0.0312 (4)
N3	0.35886 (13)	0.4957 (3)	0.31508 (10)	0.0255 (4)
C4	0.34149 (14)	0.5049 (3)	0.39488 (11)	0.0232 (4)
C5	0.29338 (17)	0.6694 (3)	0.43720 (12)	0.0291 (4)
H5	0.2638	0.8079	0.4105	0.035*
C6	0.29158 (18)	0.6177 (4)	0.52002 (13)	0.0345 (5)
H6	0.2588	0.7231	0.5513	0.041*
C7	0.33691 (17)	0.4130 (4)	0.55981 (12)	0.0332 (5)
H7	0.3349	0.3858	0.6174	0.040*
C8	0.38387 (17)	0.2517 (4)	0.51801 (13)	0.0324 (5)
H8	0.4147	0.1145	0.5453	0.039*
C9	0.38385 (15)	0.3007 (3)	0.43252 (12)	0.0256 (4)
C10	0.33293 (16)	0.6650 (3)	0.24689 (12)	0.0300 (4)
H10A	0.3745	0.6244	0.2031	0.036*
H10B	0.3648	0.8114	0.2721	0.036*
C11	0.19948 (16)	0.6862 (3)	0.20336 (11)	0.0254 (4)
C12	0.13833 (19)	0.8816 (3)	0.21182 (13)	0.0343 (5)
H12	0.1804	1.0015	0.2461	0.041*
C13	0.0167 (2)	0.9019 (4)	0.17048 (15)	0.0425 (5)
H13	−0.0246	1.0354	0.1769	0.051*
C14	−0.04510 (19)	0.7302 (4)	0.12006 (15)	0.0434 (6)
H14	−0.1285	0.7459	0.0912	0.052*
C15	0.01477 (19)	0.5340 (4)	0.11147 (13)	0.0376 (5)
H15	−0.0276	0.4148	0.0769	0.045*
C16	0.13627 (17)	0.5127 (3)	0.15333 (12)	0.0310 (4)
H16	0.1769	0.3778	0.1478	0.037*

	U11	U22	U33	U12	U13	U23
N1	0.0330 (9)	0.0294 (9)	0.0363 (9)	0.0057 (7)	0.0088 (7)	−0.0014 (7)
N2	0.0301 (8)	0.0319 (9)	0.0331 (9)	0.0056 (7)	0.0113 (7)	−0.0050 (7)
N3	0.0241 (7)	0.0282 (8)	0.0260 (8)	0.0022 (6)	0.0099 (6)	−0.0012 (6)
C4	0.0192 (8)	0.0264 (9)	0.0247 (9)	−0.0029 (7)	0.0072 (6)	−0.0010 (7)
C5	0.0314 (9)	0.0262 (10)	0.0323 (10)	0.0010 (8)	0.0133 (8)	−0.0016 (8)
C6	0.0370 (10)	0.0374 (11)	0.0331 (10)	−0.0026 (9)	0.0164 (8)	−0.0062 (9)
C7	0.0329 (10)	0.0446 (12)	0.0232 (9)	−0.0092 (9)	0.0097 (7)	0.0026 (8)
C8	0.0303 (9)	0.0327 (11)	0.0322 (10)	−0.0045 (8)	0.0059 (8)	0.0069 (8)
C9	0.0213 (8)	0.0250 (9)	0.0294 (9)	−0.0012 (7)	0.0055 (7)	0.0002 (7)
C10	0.0289 (9)	0.0354 (11)	0.0288 (9)	−0.0016 (8)	0.0130 (8)	0.0051 (8)
C11	0.0285 (9)	0.0303 (10)	0.0212 (8)	0.0005 (7)	0.0129 (7)	0.0064 (7)
C12	0.0410 (11)	0.0291 (10)	0.0356 (11)	0.0025 (9)	0.0155 (9)	0.0016 (9)
C13	0.0417 (12)	0.0384 (12)	0.0501 (13)	0.0146 (10)	0.0174 (10)	0.0082 (10)
C14	0.0303 (10)	0.0581 (15)	0.0403 (12)	0.0073 (10)	0.0074 (9)	0.0125 (11)
C15	0.0372 (11)	0.0433 (12)	0.0319 (10)	−0.0057 (9)	0.0090 (8)	−0.0009 (9)
C16	0.0345 (10)	0.0298 (10)	0.0315 (10)	0.0027 (8)	0.0137 (8)	0.0010 (8)

N1—N2	1.306 (2)	C10—C11	1.509 (2)
N1—C9	1.376 (2)	C10—H10A	0.9900
N2—N3	1.354 (2)	C10—H10B	0.9900
N3—C4	1.358 (2)	C11—C16	1.387 (3)
N3—C10	1.460 (2)	C11—C12	1.391 (3)
C4—C9	1.388 (3)	C12—C13	1.382 (3)
C4—C5	1.399 (3)	C12—H12	0.9500
C5—C6	1.376 (3)	C13—C14	1.376 (3)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.411 (3)	C14—C15	1.388 (3)
C6—H6	0.9500	C14—H14	0.9500
C7—C8	1.373 (3)	C15—C16	1.382 (3)
C7—H7	0.9500	C15—H15	0.9500
C8—C9	1.409 (3)	C16—H16	0.9500
C8—H8	0.9500
N2—N1—C9	108.00 (16)	N3—C10—H10A	109.2
N1—N2—N3	108.93 (15)	C11—C10—H10A	109.2
N2—N3—C4	110.05 (15)	N3—C10—H10B	109.2
N2—N3—C10	120.85 (15)	C11—C10—H10B	109.2
C4—N3—C10	129.11 (15)	H10A—C10—H10B	107.9
N3—C4—C9	104.45 (16)	C16—C11—C12	118.97 (18)
N3—C4—C5	132.60 (17)	C16—C11—C10	120.57 (17)
C9—C4—C5	122.94 (17)	C12—C11—C10	120.46 (18)
C6—C5—C4	115.70 (18)	C13—C12—C11	120.2 (2)
C6—C5—H5	122.2	C13—C12—H12	119.9
C4—C5—H5	122.2	C11—C12—H12	119.9
C5—C6—C7	121.96 (19)	C14—C13—C12	120.5 (2)
C5—C6—H6	119.0	C14—C13—H13	119.8
C7—C6—H6	119.0	C12—C13—H13	119.8
C8—C7—C6	122.18 (18)	C13—C14—C15	119.8 (2)
C8—C7—H7	118.9	C13—C14—H14	120.1
C6—C7—H7	118.9	C15—C14—H14	120.1
C7—C8—C9	116.38 (18)	C16—C15—C14	119.8 (2)
C7—C8—H8	121.8	C16—C15—H15	120.1
C9—C8—H8	121.8	C14—C15—H15	120.1
N1—C9—C4	108.56 (16)	C15—C16—C11	120.71 (19)
N1—C9—C8	130.63 (18)	C15—C16—H16	119.6
C4—C9—C8	120.80 (18)	C11—C16—H16	119.6
N3—C10—C11	111.88 (15)
C9—N1—N2—N3	−0.1 (2)	N3—C4—C9—C8	177.98 (16)
N1—N2—N3—C4	−0.4 (2)	C5—C4—C9—C8	−2.1 (3)
N1—N2—N3—C10	179.31 (15)	C7—C8—C9—N1	−179.62 (19)
N2—N3—C4—C9	0.78 (18)	C7—C8—C9—C4	1.9 (3)
C10—N3—C4—C9	−178.94 (17)	N2—N3—C10—C11	106.88 (18)
N2—N3—C4—C5	−179.12 (18)	C4—N3—C10—C11	−73.4 (2)
C10—N3—C4—C5	1.2 (3)	N3—C10—C11—C16	−67.4 (2)
N3—C4—C5—C6	−179.41 (18)	N3—C10—C11—C12	113.53 (19)
C9—C4—C5—C6	0.7 (3)	C16—C11—C12—C13	−0.3 (3)
C4—C5—C6—C7	0.8 (3)	C10—C11—C12—C13	178.74 (17)
C5—C6—C7—C8	−1.0 (3)	C11—C12—C13—C14	−0.5 (3)
C6—C7—C8—C9	−0.4 (3)	C12—C13—C14—C15	0.8 (3)
N2—N1—C9—C4	0.6 (2)	C13—C14—C15—C16	−0.3 (3)
N2—N1—C9—C8	−178.05 (18)	C14—C15—C16—C11	−0.5 (3)
N3—C4—C9—N1	−0.84 (19)	C12—C11—C16—C15	0.9 (3)
C5—C4—C9—N1	179.07 (17)	C10—C11—C16—C15	−178.22 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1i	0.95	2.62	3.513 (3)	158
C14—H14···Cgii	0.95	2.69	3.583 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N1i	0.95	2.62	3.513 (3)	158
C14—H14⋯Cgii	0.95	2.69	3.583 (2)	157

Symmetry codes: (i) ; (ii) .