1-Benz-yloxy-1H-benzotriazole.

In the title compound, C(13)H(11)N(3)O, the dihedral angle between the benzotriazole ring system [maximum deviation = 0.027 (16) Å] and the benzene ring is 10.28 (9)°. The C-C-O-N bond adopts an anti conformation [torsion angle = -177.11 (16)°]. In the crystal, the mol-ecules inter-act via weak C-H⋯π inter-actions and aromatic π-π stacking [centroid-to-centroid distance = 3.731 (12) Å].

Related literature

For a related structure and background to benzotriazoles, see: Selvarathy Grace et al. (2012 ▶).

Experimental

Crystal data

C13H11N3O

M = 225.25

Orthorhombic,

a = 11.2417 (5) Å

b = 7.8381 (8) Å

c = 25.3933 (18) Å

V = 2237.5 (3) Å3

Z = 8

Cu Kα radiation

μ = 0.72 mm−1

T = 193 K

0.51 × 0.45 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Wiehl & Schollmeyer, 1994 ▶) T min = 0.84, T max = 0.99

2125 measured reflections

2125 independent reflections

1867 reflections with I > 2σ(I)

R int = 0.000

3 standard reflections every 60 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.163

S = 1.12

2125 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (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/S1600536812028395/hb6865sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028395/hb6865Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028395/hb6865Isup3.cml

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

C13H11N3O	F(000) = 944
Mr = 225.25	Dx = 1.337 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 11.2417 (5) Å	θ = 60–70°
b = 7.8381 (8) Å	µ = 0.72 mm−1
c = 25.3933 (18) Å	T = 193 K
V = 2237.5 (3) Å3	Block, colourless
Z = 8	0.51 × 0.45 × 0.13 mm

Enraf–Nonius CAD-4 diffractometer	1867 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.000
Graphite monochromator	θmax = 70.0°, θmin = 3.5°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (CORINC; Wiehl & Schollmeyer, 1994)	k = −9→0
Tmin = 0.84, Tmax = 0.99	l = 0→30
2125 measured reflections	3 standard reflections every 60 min
2125 independent reflections	intensity decay: 3%

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0919P)2 + 0.968P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2125 reflections	Δρmax = 0.26 e Å−3
155 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (5)

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	0.59619 (14)	0.1616 (2)	0.41567 (6)	0.0319 (4)
N2	0.69169 (16)	0.0710 (2)	0.40089 (7)	0.0386 (5)
N3	0.74822 (17)	0.0253 (3)	0.44366 (6)	0.0390 (5)
C4	0.68515 (16)	0.0849 (3)	0.48621 (7)	0.0300 (4)
C5	0.70541 (19)	0.0634 (3)	0.54041 (8)	0.0363 (5)
H5	0.7724	0.0020	0.5531	0.044*
C6	0.6242 (2)	0.1348 (3)	0.57406 (8)	0.0395 (5)
H6	0.6348	0.1216	0.6110	0.047*
C7	0.5253 (2)	0.2276 (3)	0.55539 (8)	0.0390 (5)
H7	0.4719	0.2767	0.5802	0.047*
C8	0.50350 (18)	0.2493 (3)	0.50265 (9)	0.0342 (5)
H8	0.4366	0.3111	0.4900	0.041*
C9	0.58618 (17)	0.1744 (2)	0.46878 (7)	0.0285 (4)
O10	0.51465 (12)	0.21382 (19)	0.37887 (5)	0.0364 (4)
C11	0.56357 (18)	0.3549 (3)	0.34807 (8)	0.0373 (5)
H11A	0.6347	0.3171	0.3283	0.045*
H11B	0.5867	0.4503	0.3715	0.045*
C12	0.46776 (17)	0.4101 (3)	0.31104 (7)	0.0296 (5)
C13	0.47315 (18)	0.3682 (3)	0.25810 (8)	0.0352 (5)
H13	0.5377	0.3018	0.2453	0.042*
C14	0.3853 (2)	0.4220 (3)	0.22357 (8)	0.0400 (5)
H14	0.3901	0.3931	0.1873	0.048*
C15	0.29088 (19)	0.5177 (3)	0.24185 (9)	0.0398 (5)
H15	0.2310	0.5551	0.2181	0.048*
C16	0.28349 (19)	0.5589 (3)	0.29457 (9)	0.0403 (5)
H16	0.2177	0.6229	0.3073	0.048*
C17	0.37194 (18)	0.5069 (3)	0.32891 (8)	0.0357 (5)
H17	0.3673	0.5374	0.3651	0.043*

	U11	U22	U33	U12	U13	U23
N1	0.0274 (8)	0.0424 (9)	0.0260 (8)	0.0042 (7)	−0.0039 (6)	0.0034 (7)
N2	0.0322 (9)	0.0523 (11)	0.0314 (9)	0.0075 (8)	0.0002 (7)	−0.0007 (8)
N3	0.0316 (9)	0.0526 (11)	0.0330 (9)	0.0102 (8)	−0.0019 (7)	0.0024 (8)
C4	0.0233 (9)	0.0355 (10)	0.0311 (10)	−0.0005 (8)	−0.0026 (7)	0.0002 (8)
C5	0.0341 (10)	0.0432 (11)	0.0315 (10)	−0.0023 (9)	−0.0080 (8)	0.0044 (8)
C6	0.0417 (12)	0.0485 (12)	0.0284 (10)	−0.0087 (10)	−0.0031 (9)	−0.0010 (9)
C7	0.0376 (11)	0.0432 (12)	0.0361 (11)	−0.0059 (9)	0.0075 (9)	−0.0062 (9)
C8	0.0263 (9)	0.0357 (10)	0.0406 (10)	−0.0003 (8)	0.0011 (8)	0.0017 (8)
C9	0.0256 (9)	0.0327 (9)	0.0273 (9)	−0.0029 (8)	−0.0028 (7)	0.0015 (7)
O10	0.0279 (7)	0.0507 (9)	0.0307 (7)	−0.0054 (6)	−0.0097 (5)	0.0121 (6)
C11	0.0307 (10)	0.0430 (11)	0.0383 (11)	−0.0080 (9)	−0.0074 (8)	0.0124 (9)
C12	0.0260 (9)	0.0330 (10)	0.0299 (9)	−0.0056 (8)	−0.0038 (7)	0.0051 (7)
C13	0.0326 (11)	0.0393 (11)	0.0337 (11)	0.0015 (8)	0.0022 (8)	0.0015 (8)
C14	0.0492 (13)	0.0426 (11)	0.0283 (10)	−0.0043 (10)	−0.0074 (9)	0.0020 (8)
C15	0.0340 (11)	0.0382 (11)	0.0473 (13)	−0.0052 (9)	−0.0175 (9)	0.0095 (9)
C16	0.0278 (10)	0.0401 (11)	0.0530 (13)	0.0023 (9)	0.0001 (9)	0.0029 (10)
C17	0.0345 (11)	0.0409 (11)	0.0317 (10)	−0.0044 (9)	0.0018 (8)	0.0012 (8)

N1—N2	1.341 (2)	O10—C11	1.462 (2)
N1—C9	1.357 (2)	C11—C12	1.494 (3)
N1—O10	1.3714 (19)	C11—H11A	0.9900
N2—N3	1.308 (2)	C11—H11B	0.9900
N3—C4	1.374 (3)	C12—C13	1.385 (3)
C4—C9	1.388 (3)	C12—C17	1.393 (3)
C4—C5	1.405 (3)	C13—C14	1.386 (3)
C5—C6	1.370 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—C15	1.380 (3)
C6—C7	1.411 (3)	C14—H14	0.9500
C6—H6	0.9500	C15—C16	1.380 (3)
C7—C8	1.372 (3)	C15—H15	0.9500
C7—H7	0.9500	C16—C17	1.384 (3)
C8—C9	1.396 (3)	C16—H16	0.9500
C8—H8	0.9500	C17—H17	0.9500
N2—N1—C9	112.56 (15)	O10—C11—C12	106.54 (15)
N2—N1—O10	120.16 (15)	O10—C11—H11A	110.4
C9—N1—O10	126.85 (16)	C12—C11—H11A	110.4
N3—N2—N1	107.55 (16)	O10—C11—H11B	110.4
N2—N3—C4	108.00 (17)	C12—C11—H11B	110.4
N3—C4—C9	109.55 (17)	H11A—C11—H11B	108.6
N3—C4—C5	130.21 (19)	C13—C12—C17	118.63 (18)
C9—C4—C5	120.21 (18)	C13—C12—C11	120.70 (19)
C6—C5—C4	116.99 (19)	C17—C12—C11	120.66 (18)
C6—C5—H5	121.5	C12—C13—C14	120.7 (2)
C4—C5—H5	121.5	C12—C13—H13	119.7
C5—C6—C7	121.75 (19)	C14—C13—H13	119.7
C5—C6—H6	119.1	C15—C14—C13	120.04 (19)
C7—C6—H6	119.1	C15—C14—H14	120.0
C8—C7—C6	122.2 (2)	C13—C14—H14	120.0
C8—C7—H7	118.9	C16—C15—C14	119.99 (19)
C6—C7—H7	118.9	C16—C15—H15	120.0
C7—C8—C9	115.53 (19)	C14—C15—H15	120.0
C7—C8—H8	122.2	C15—C16—C17	119.9 (2)
C9—C8—H8	122.2	C15—C16—H16	120.0
N1—C9—C4	102.31 (16)	C17—C16—H16	120.0
N1—C9—C8	134.33 (18)	C16—C17—C12	120.70 (19)
C4—C9—C8	123.35 (18)	C16—C17—H17	119.7
N1—O10—C11	109.80 (14)	C12—C17—H17	119.7
C9—N1—N2—N3	−1.4 (2)	C5—C4—C9—C8	1.0 (3)
O10—N1—N2—N3	−174.41 (17)	C7—C8—C9—N1	177.9 (2)
N1—N2—N3—C4	1.5 (2)	C7—C8—C9—C4	−0.6 (3)
N2—N3—C4—C9	−1.2 (2)	N2—N1—O10—C11	−74.3 (2)
N2—N3—C4—C5	176.8 (2)	C9—N1—O10—C11	113.8 (2)
N3—C4—C5—C6	−178.2 (2)	N1—O10—C11—C12	−177.11 (16)
C9—C4—C5—C6	−0.3 (3)	O10—C11—C12—C13	−104.8 (2)
C4—C5—C6—C7	−0.7 (3)	O10—C11—C12—C17	76.1 (2)
C5—C6—C7—C8	1.1 (3)	C17—C12—C13—C14	0.3 (3)
C6—C7—C8—C9	−0.4 (3)	C11—C12—C13—C14	−178.85 (19)
N2—N1—C9—C4	0.7 (2)	C12—C13—C14—C15	−0.4 (3)
O10—N1—C9—C4	173.08 (18)	C13—C14—C15—C16	−0.4 (3)
N2—N1—C9—C8	−178.1 (2)	C14—C15—C16—C17	1.2 (3)
O10—N1—C9—C8	−5.7 (4)	C15—C16—C17—C12	−1.2 (3)
N3—C4—C9—N1	0.3 (2)	C13—C12—C17—C16	0.5 (3)
C5—C4—C9—N1	−177.93 (19)	C11—C12—C17—C16	179.64 (19)
N3—C4—C9—C8	179.28 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1i	0.95	2.86	3.685 (2)	145
C16—H16···Cg1ii	0.95	2.99	3.691 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cg1i	0.95	2.86	3.685 (2)	145
C16—H16⋯Cg1ii	0.95	2.99	3.691 (3)	132

Symmetry codes: (i) ; (ii) .