1-(2,3,5,6-Tetra-methyl-benz-yloxy)-1H-benzotriazole.

In the title compound, C(17)H(19)N(3)O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069 (15) Å. The mean plane of the benzotriazole ring forms a dihedral angle of 13.16 (4)° with the mean plane of the benzene ring. The crystal packing is stabilized by π-π stacking inter-actions, with a centroid-centroid distance of 3.8077 (12) Å, together with weak C-H⋯π inter-actions. Mol-ecules are stacked along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the biological activity of N-oxide and benzotriazole derivatives, see: Katarzyna et al. (2005 ▶); Sarala et al. (2007 ▶). For applications of benzotriazole, see: Kopec et al. (2008 ▶); Krawczyk & Gdaniec (2005 ▶); Smith et al. (2001 ▶); Sha et al. (1996 ▶). For 1-hydroxy­benzotriazole, see: Anderson et al. (1963 ▶); Bosch et al. (1983 ▶).

Experimental

Crystal data

C17H19N3O

M = 281.35

Monoclinic,

a = 4.9737 (8) Å

b = 26.3838 (18) Å

c = 11.490 (2) Å

β = 105.977 (7)°

V = 1449.5 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.65 mm−1

T = 193 K

0.51 × 0.51 × 0.45 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971 ▶) T min = 0.731, T max = 0.759

2861 measured reflections

2729 independent reflections

2578 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections frequency: 60 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.08

2729 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: CORINC (Draeger & Gattow, 1971 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010794/at2749sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010794/at2749Isup2.hkl

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

C17H19N3O	F(000) = 600
Mr = 281.35	Dx = 1.289 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 4.9737 (8) Å	θ = 65–70°
b = 26.3838 (18) Å	µ = 0.65 mm−1
c = 11.490 (2) Å	T = 193 K
β = 105.977 (7)°	Block, colourless
V = 1449.5 (4) Å3	0.51 × 0.51 × 0.45 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2578 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.050
graphite	θmax = 69.9°, θmin = 3.4°
ω/2θ scans	h = −5→6
Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971)	k = 0→32
Tmin = 0.731, Tmax = 0.759	l = −13→0
2861 measured reflections	3 standard reflections every 60 min
2729 independent reflections	intensity decay: 1%

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.687P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.002
2729 reflections	Δρmax = 0.27 e Å−3
195 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: 0.0042 (6)

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
N1	0.4809 (3)	0.32620 (5)	0.62810 (11)	0.0311 (3)
N2	0.3357 (3)	0.28455 (5)	0.63903 (13)	0.0379 (4)
N3	0.4680 (3)	0.26168 (5)	0.73894 (13)	0.0395 (4)
C4	0.7028 (3)	0.28997 (6)	0.79380 (14)	0.0321 (4)
C5	0.9114 (4)	0.28229 (6)	0.90326 (15)	0.0374 (4)
H5	0.9065	0.2539	0.9536	0.045*
C6	1.1208 (4)	0.31732 (7)	0.93407 (15)	0.0411 (4)
H6	1.2652	0.3131	1.0072	0.049*
C7	1.1281 (4)	0.35962 (7)	0.86002 (16)	0.0412 (4)
H7	1.2779	0.3831	0.8849	0.049*
C8	0.9264 (3)	0.36815 (6)	0.75324 (15)	0.0348 (4)
H8	0.9317	0.3967	0.7036	0.042*
C9	0.7132 (3)	0.33208 (6)	0.72239 (13)	0.0292 (4)
O10	0.3754 (2)	0.35998 (4)	0.53578 (9)	0.0327 (3)
C11	0.4691 (4)	0.34745 (6)	0.42841 (14)	0.0328 (4)
H11A	0.3904	0.3145	0.3939	0.039*
H11B	0.6757	0.3455	0.4497	0.039*
C12	0.3636 (3)	0.38958 (6)	0.33973 (13)	0.0286 (4)
C13	0.5113 (3)	0.43544 (6)	0.35296 (13)	0.0296 (4)
C14	0.4080 (3)	0.47548 (6)	0.27302 (14)	0.0316 (4)
C15	0.1584 (3)	0.46843 (6)	0.18303 (14)	0.0335 (4)
H15	0.0869	0.4957	0.1294	0.040*
C16	0.0095 (3)	0.42330 (7)	0.16838 (13)	0.0318 (4)
C17	0.1116 (3)	0.38296 (6)	0.24756 (13)	0.0299 (4)
C18	0.7813 (3)	0.44365 (7)	0.45103 (15)	0.0389 (4)
H18A	0.8466	0.4113	0.4906	0.058*
H18B	0.7492	0.4676	0.5110	0.058*
H18C	0.9231	0.4574	0.4151	0.058*
C19	0.5633 (4)	0.52490 (7)	0.28165 (18)	0.0424 (4)
H19A	0.7451	0.5190	0.2664	0.064*
H19B	0.5917	0.5392	0.3628	0.064*
H19C	0.4541	0.5487	0.2214	0.064*
C20	−0.2599 (4)	0.41887 (8)	0.06843 (15)	0.0416 (4)
H20A	−0.3033	0.4515	0.0268	0.062*
H20B	−0.4120	0.4093	0.1031	0.062*
H20C	−0.2393	0.3929	0.0106	0.062*
C21	−0.0499 (4)	0.33394 (7)	0.23361 (17)	0.0399 (4)
H21A	−0.0717	0.3235	0.3124	0.060*
H21B	0.0518	0.3076	0.2029	0.060*
H21C	−0.2348	0.3388	0.1765	0.060*

	U11	U22	U33	U12	U13	U23
N1	0.0347 (7)	0.0312 (7)	0.0230 (6)	−0.0011 (5)	0.0005 (5)	0.0022 (5)
N2	0.0426 (8)	0.0353 (8)	0.0313 (7)	−0.0056 (6)	0.0026 (6)	−0.0011 (6)
N3	0.0478 (9)	0.0343 (8)	0.0321 (7)	−0.0046 (6)	0.0038 (6)	0.0008 (6)
C4	0.0364 (8)	0.0301 (8)	0.0273 (8)	0.0026 (6)	0.0048 (6)	−0.0007 (6)
C5	0.0464 (10)	0.0351 (9)	0.0268 (8)	0.0078 (7)	0.0035 (7)	0.0042 (6)
C6	0.0385 (9)	0.0508 (10)	0.0275 (8)	0.0071 (8)	−0.0018 (7)	−0.0006 (7)
C7	0.0345 (9)	0.0477 (10)	0.0355 (9)	−0.0059 (7)	−0.0002 (7)	−0.0041 (7)
C8	0.0370 (9)	0.0347 (8)	0.0298 (8)	−0.0028 (7)	0.0044 (7)	0.0011 (6)
C9	0.0301 (8)	0.0318 (8)	0.0233 (7)	0.0041 (6)	0.0033 (6)	−0.0019 (6)
O10	0.0379 (6)	0.0353 (6)	0.0213 (5)	0.0086 (5)	0.0021 (4)	0.0026 (4)
C11	0.0380 (9)	0.0338 (8)	0.0248 (8)	0.0063 (7)	0.0055 (6)	−0.0015 (6)
C12	0.0305 (8)	0.0325 (8)	0.0222 (7)	0.0049 (6)	0.0062 (6)	−0.0013 (6)
C13	0.0281 (8)	0.0357 (8)	0.0240 (7)	0.0018 (6)	0.0057 (6)	−0.0040 (6)
C14	0.0339 (8)	0.0331 (8)	0.0295 (8)	0.0019 (6)	0.0114 (6)	−0.0019 (6)
C15	0.0349 (8)	0.0374 (9)	0.0275 (8)	0.0089 (7)	0.0077 (6)	0.0051 (6)
C16	0.0293 (8)	0.0428 (9)	0.0219 (7)	0.0046 (7)	0.0048 (6)	−0.0019 (6)
C17	0.0305 (8)	0.0351 (8)	0.0237 (7)	0.0011 (6)	0.0070 (6)	−0.0040 (6)
C18	0.0338 (9)	0.0460 (10)	0.0320 (9)	−0.0027 (7)	0.0009 (7)	−0.0053 (7)
C19	0.0456 (10)	0.0354 (9)	0.0483 (10)	−0.0028 (8)	0.0163 (8)	−0.0016 (8)
C20	0.0344 (9)	0.0580 (11)	0.0266 (8)	0.0056 (8)	−0.0012 (7)	−0.0019 (7)
C21	0.0380 (9)	0.0401 (9)	0.0403 (9)	−0.0046 (7)	0.0086 (7)	−0.0045 (7)

N1—N2	1.3398 (19)	C13—C14	1.401 (2)
N1—C9	1.358 (2)	C13—C18	1.512 (2)
N1—O10	1.3741 (16)	C14—C15	1.392 (2)
N2—N3	1.304 (2)	C14—C19	1.505 (2)
N3—C4	1.383 (2)	C15—C16	1.388 (2)
C4—C9	1.390 (2)	C15—H15	0.9500
C4—C5	1.407 (2)	C16—C17	1.401 (2)
C5—C6	1.364 (3)	C16—C20	1.510 (2)
C5—H5	0.9500	C17—C21	1.508 (2)
C6—C7	1.410 (3)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.373 (2)	C18—H18C	0.9800
C7—H7	0.9500	C19—H19A	0.9800
C8—C9	1.396 (2)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
O10—C11	1.4714 (19)	C20—H20A	0.9800
C11—C12	1.501 (2)	C20—H20B	0.9800
C11—H11A	0.9900	C20—H20C	0.9800
C11—H11B	0.9900	C21—H21A	0.9800
C12—C13	1.402 (2)	C21—H21B	0.9800
C12—C17	1.412 (2)	C21—H21C	0.9800
N2—N1—C9	112.41 (13)	C15—C14—C13	118.49 (15)
N2—N1—O10	120.21 (12)	C15—C14—C19	120.09 (15)
C9—N1—O10	127.02 (13)	C13—C14—C19	121.41 (15)
N3—N2—N1	107.93 (13)	C16—C15—C14	122.80 (15)
N2—N3—C4	108.04 (14)	C16—C15—H15	118.6
N3—C4—C9	109.04 (14)	C14—C15—H15	118.6
N3—C4—C5	130.67 (16)	C15—C16—C17	119.15 (14)
C9—C4—C5	120.29 (15)	C15—C16—C20	119.39 (15)
C6—C5—C4	117.17 (16)	C17—C16—C20	121.45 (16)
C6—C5—H5	121.4	C16—C17—C12	118.77 (15)
C4—C5—H5	121.4	C16—C17—C21	119.69 (14)
C5—C6—C7	121.62 (16)	C12—C17—C21	121.53 (14)
C5—C6—H6	119.2	C13—C18—H18A	109.5
C7—C6—H6	119.2	C13—C18—H18B	109.5
C8—C7—C6	122.35 (16)	H18A—C18—H18B	109.5
C8—C7—H7	118.8	C13—C18—H18C	109.5
C6—C7—H7	118.8	H18A—C18—H18C	109.5
C7—C8—C9	115.62 (15)	H18B—C18—H18C	109.5
C7—C8—H8	122.2	C14—C19—H19A	109.5
C9—C8—H8	122.2	C14—C19—H19B	109.5
N1—C9—C4	102.58 (14)	H19A—C19—H19B	109.5
N1—C9—C8	134.47 (15)	C14—C19—H19C	109.5
C4—C9—C8	122.95 (15)	H19A—C19—H19C	109.5
N1—O10—C11	111.09 (11)	H19B—C19—H19C	109.5
O10—C11—C12	105.69 (12)	C16—C20—H20A	109.5
O10—C11—H11A	110.6	C16—C20—H20B	109.5
C12—C11—H11A	110.6	H20A—C20—H20B	109.5
O10—C11—H11B	110.6	C16—C20—H20C	109.5
C12—C11—H11B	110.6	H20A—C20—H20C	109.5
H11A—C11—H11B	108.7	H20B—C20—H20C	109.5
C13—C12—C17	121.24 (14)	C17—C21—H21A	109.5
C13—C12—C11	119.37 (14)	C17—C21—H21B	109.5
C17—C12—C11	119.33 (14)	H21A—C21—H21B	109.5
C14—C13—C12	119.53 (14)	C17—C21—H21C	109.5
C14—C13—C18	118.07 (15)	H21A—C21—H21C	109.5
C12—C13—C18	122.39 (14)	H21B—C21—H21C	109.5
C9—N1—N2—N3	−0.72 (19)	O10—C11—C12—C13	80.40 (17)
O10—N1—N2—N3	−174.26 (13)	O10—C11—C12—C17	−97.09 (16)
N1—N2—N3—C4	0.67 (18)	C17—C12—C13—C14	−0.3 (2)
N2—N3—C4—C9	−0.41 (19)	C11—C12—C13—C14	−177.69 (14)
N2—N3—C4—C5	179.01 (17)	C17—C12—C13—C18	179.83 (14)
N3—C4—C5—C6	179.99 (17)	C11—C12—C13—C18	2.4 (2)
C9—C4—C5—C6	−0.6 (2)	C12—C13—C14—C15	0.6 (2)
C4—C5—C6—C7	0.3 (3)	C18—C13—C14—C15	−179.49 (14)
C5—C6—C7—C8	0.1 (3)	C12—C13—C14—C19	−178.35 (14)
C6—C7—C8—C9	−0.1 (3)	C18—C13—C14—C19	1.6 (2)
N2—N1—C9—C4	0.44 (17)	C13—C14—C15—C16	−0.7 (2)
O10—N1—C9—C4	173.45 (14)	C19—C14—C15—C16	178.23 (15)
N2—N1—C9—C8	−179.69 (17)	C14—C15—C16—C17	0.5 (2)
O10—N1—C9—C8	−6.7 (3)	C14—C15—C16—C20	179.92 (15)
N3—C4—C9—N1	−0.01 (17)	C15—C16—C17—C12	−0.1 (2)
C5—C4—C9—N1	−179.51 (15)	C20—C16—C17—C12	−179.53 (14)
N3—C4—C9—C8	−179.90 (15)	C15—C16—C17—C21	179.26 (14)
C5—C4—C9—C8	0.6 (2)	C20—C16—C17—C21	−0.2 (2)
C7—C8—C9—N1	179.94 (17)	C13—C12—C17—C16	0.0 (2)
C7—C8—C9—C4	−0.2 (2)	C11—C12—C17—C16	177.45 (13)
N2—N1—O10—C11	−91.18 (17)	C13—C12—C17—C21	−179.36 (14)
C9—N1—O10—C11	96.30 (17)	C11—C12—C17—C21	−1.9 (2)
N1—O10—C11—C12	−174.71 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···Cg3i	0.98	2.85	3.6701 (18)	141
C20—H20B···Cg3ii	0.98	2.80	3.682 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18C⋯Cg3i	0.98	2.85	3.6701 (18)	141
C20—H20B⋯Cg3ii	0.98	2.80	3.682 (2)	150

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of the C12–C17 ring.