1-[2-(2,5-Dichloro-benz-yloxy)-2-phenyl-eth-yl]-1H-benzotriazole.

In the title mol-ecule, C(21)H(17)Cl(2)N(3)O, the benzotriazole ring is oriented at dihedral angles of 48.72 (6) and 62.94 (5)°, respectively, to the phenyl and benzene rings and the dihedral angle between the phenyl and benzene rings is 88.95 (6)°. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into chains. π-π contacts between the triazole and benzene rings [centroid-centroid distance = 3.678 (1) Å] and a weak C-H⋯π inter-action are also observed.

Related literature

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998 ▶); Yu et al. (2003 ▶); Kopanska et al. (2004 ▶). For related structures, see: Katritzky et al. (2001 ▶); Özel Güven et al. (2007a ▶,b ▶, 2010a ▶,b ▶, 2011 ▶); Swamy et al. (2006 ▶).

Experimental

Crystal data

C21H17Cl2N3O

M = 398.28

Triclinic,

a = 8.6970 (3) Å

b = 8.8385 (3) Å

c = 13.3918 (4) Å

α = 105.840 (3)°

β = 104.453 (3)°

γ = 99.713 (2)°

V = 927.47 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 120 K

0.20 × 0.13 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.930, T max = 0.971

21356 measured reflections

4271 independent reflections

3391 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.12

4271 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.50 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044783/su2333sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044783/su2333Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044783/su2333Isup3.cml

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

C21H17Cl2N3O	Z = 2
Mr = 398.28	F(000) = 412
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6970 (3) Å	Cell parameters from 14295 reflections
b = 8.8385 (3) Å	θ = 2.9–27.5°
c = 13.3918 (4) Å	µ = 0.37 mm−1
α = 105.840 (3)°	T = 120 K
β = 104.453 (3)°	Block, colorless
γ = 99.713 (2)°	0.20 × 0.13 × 0.08 mm
V = 927.47 (6) Å3

Bruker–Nonius KappaCCD diffractometer	4271 independent reflections
Radiation source: fine-focus sealed tube	3391 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −11→11
Tmin = 0.930, Tmax = 0.971	k = −11→11
21356 measured reflections	l = −17→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.2097P] where P = (Fo2 + 2Fc2)/3
4271 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.50 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
Cl1	1.14499 (5)	0.89780 (6)	0.93114 (4)	0.02094 (14)
Cl2	0.71261 (6)	0.46919 (6)	1.10951 (4)	0.02373 (14)
O1	0.61227 (15)	0.66913 (16)	0.77690 (10)	0.0196 (3)
N1	0.25973 (19)	0.61345 (19)	0.54291 (12)	0.0178 (3)
N2	0.2767 (2)	0.5667 (2)	0.44128 (12)	0.0224 (4)
N3	0.1660 (2)	0.6091 (2)	0.37527 (12)	0.0229 (4)
C1	0.5343 (2)	0.7104 (2)	0.68405 (14)	0.0164 (4)
H1	0.5981	0.6965	0.6329	0.020*
C2	0.5167 (2)	0.8836 (2)	0.71551 (14)	0.0171 (4)
C3	0.5459 (2)	0.9801 (2)	0.65228 (15)	0.0224 (4)
H3	0.5803	0.9394	0.5922	0.027*
C4	0.5241 (3)	1.1372 (3)	0.67827 (18)	0.0297 (5)
H4	0.5451	1.2016	0.6362	0.036*
C5	0.4709 (2)	1.1970 (3)	0.76725 (18)	0.0307 (5)
H5	0.4540	1.3009	0.7841	0.037*
C6	0.4431 (2)	1.1023 (3)	0.83084 (17)	0.0304 (5)
H6	0.4084	1.1432	0.8908	0.036*
C7	0.4665 (2)	0.9469 (2)	0.80589 (15)	0.0230 (4)
H7	0.4486	0.8844	0.8496	0.028*
C8	0.3692 (2)	0.5830 (2)	0.63280 (14)	0.0200 (4)
H8A	0.3884	0.4765	0.6063	0.024*
H8B	0.3164	0.5821	0.6885	0.024*
C9	0.1356 (2)	0.6899 (2)	0.54283 (14)	0.0172 (4)
C10	0.0700 (2)	0.7613 (2)	0.62427 (15)	0.0214 (4)
H10	0.1098	0.7626	0.6958	0.026*
C11	−0.0566 (2)	0.8293 (3)	0.59197 (16)	0.0244 (4)
H11	−0.1025	0.8795	0.6436	0.029*
C12	−0.1196 (2)	0.8254 (2)	0.48260 (16)	0.0238 (4)
H12	−0.2064	0.8717	0.4643	0.029*
C13	−0.0554 (2)	0.7549 (2)	0.40323 (15)	0.0220 (4)
H13	−0.0968	0.7527	0.3316	0.026*
C14	0.0754 (2)	0.6861 (2)	0.43453 (14)	0.0179 (4)
C15	0.7840 (2)	0.7424 (2)	0.81794 (14)	0.0184 (4)
H15A	0.8037	0.8585	0.8309	0.022*
H15B	0.8360	0.6971	0.7646	0.022*
C16	0.8562 (2)	0.7120 (2)	0.92259 (14)	0.0157 (4)
C17	1.0225 (2)	0.7779 (2)	0.98111 (14)	0.0159 (4)
C18	1.0947 (2)	0.7531 (2)	1.07830 (14)	0.0190 (4)
H18	1.2057	0.7998	1.1157	0.023*
C19	1.0001 (2)	0.6582 (2)	1.11903 (14)	0.0197 (4)
H19	1.0464	0.6388	1.1834	0.024*
C20	0.8346 (2)	0.5930 (2)	1.06155 (14)	0.0176 (4)
C21	0.7616 (2)	0.6186 (2)	0.96475 (14)	0.0173 (4)
H21	0.6501	0.5735	0.9284	0.021*

	U11	U22	U33	U12	U13	U23
Cl1	0.0188 (2)	0.0214 (3)	0.0219 (2)	0.00319 (19)	0.00663 (19)	0.00705 (19)
Cl2	0.0264 (3)	0.0283 (3)	0.0226 (2)	0.0087 (2)	0.0116 (2)	0.0132 (2)
O1	0.0155 (7)	0.0245 (7)	0.0166 (6)	0.0027 (5)	−0.0012 (5)	0.0103 (5)
N1	0.0169 (8)	0.0191 (8)	0.0136 (7)	0.0020 (6)	0.0000 (6)	0.0053 (6)
N2	0.0253 (9)	0.0251 (9)	0.0137 (7)	0.0057 (7)	0.0029 (7)	0.0050 (7)
N3	0.0253 (9)	0.0257 (9)	0.0157 (7)	0.0075 (7)	0.0026 (7)	0.0066 (7)
C1	0.0153 (9)	0.0209 (9)	0.0124 (8)	0.0048 (7)	0.0015 (7)	0.0070 (7)
C2	0.0088 (8)	0.0200 (9)	0.0168 (8)	0.0013 (7)	−0.0019 (7)	0.0042 (7)
C3	0.0172 (10)	0.0272 (11)	0.0205 (9)	0.0043 (8)	0.0015 (8)	0.0094 (8)
C4	0.0226 (11)	0.0273 (11)	0.0355 (12)	0.0043 (9)	−0.0021 (9)	0.0160 (9)
C5	0.0179 (10)	0.0170 (10)	0.0434 (12)	0.0060 (8)	−0.0049 (9)	0.0007 (9)
C6	0.0184 (10)	0.0312 (12)	0.0318 (11)	0.0041 (9)	0.0057 (9)	−0.0014 (9)
C7	0.0178 (10)	0.0261 (11)	0.0200 (9)	0.0016 (8)	0.0044 (8)	0.0033 (8)
C8	0.0198 (10)	0.0202 (10)	0.0157 (8)	0.0025 (8)	−0.0020 (7)	0.0074 (7)
C9	0.0144 (9)	0.0175 (9)	0.0155 (8)	−0.0013 (7)	−0.0001 (7)	0.0065 (7)
C10	0.0186 (10)	0.0256 (10)	0.0177 (9)	0.0013 (8)	0.0046 (8)	0.0074 (8)
C11	0.0214 (10)	0.0270 (11)	0.0240 (10)	0.0037 (8)	0.0086 (8)	0.0072 (8)
C12	0.0165 (10)	0.0230 (10)	0.0291 (10)	0.0025 (8)	0.0026 (8)	0.0101 (8)
C13	0.0218 (10)	0.0204 (10)	0.0194 (9)	0.0005 (8)	0.0000 (8)	0.0086 (8)
C14	0.0180 (9)	0.0166 (9)	0.0143 (8)	−0.0011 (7)	0.0005 (7)	0.0049 (7)
C15	0.0169 (9)	0.0193 (10)	0.0159 (8)	0.0033 (8)	0.0010 (7)	0.0055 (7)
C16	0.0169 (9)	0.0148 (9)	0.0132 (8)	0.0068 (7)	0.0029 (7)	0.0013 (7)
C17	0.0157 (9)	0.0156 (9)	0.0184 (8)	0.0064 (7)	0.0070 (7)	0.0056 (7)
C18	0.0132 (9)	0.0241 (10)	0.0155 (8)	0.0065 (8)	0.0003 (7)	0.0024 (7)
C19	0.0210 (10)	0.0270 (10)	0.0135 (8)	0.0124 (8)	0.0050 (7)	0.0072 (8)
C20	0.0188 (9)	0.0200 (9)	0.0162 (8)	0.0069 (8)	0.0079 (7)	0.0060 (7)
C21	0.0142 (9)	0.0188 (9)	0.0158 (8)	0.0052 (7)	0.0018 (7)	0.0032 (7)

Cl1—C17	1.7518 (19)	C8—H8B	0.9700
Cl2—C20	1.7514 (19)	C9—C10	1.404 (3)
O1—C1	1.432 (2)	C10—C11	1.374 (3)
O1—C15	1.422 (2)	C10—H10	0.9300
N1—N2	1.363 (2)	C11—H11	0.9300
N1—C8	1.456 (2)	C12—C11	1.418 (3)
N1—C9	1.366 (2)	C12—H12	0.9300
N3—N2	1.314 (2)	C13—C12	1.372 (3)
N3—C14	1.383 (2)	C13—C14	1.405 (3)
C1—C8	1.530 (3)	C13—H13	0.9300
C1—H1	0.9800	C14—C9	1.403 (2)
C2—C1	1.517 (3)	C15—H15A	0.9700
C2—C3	1.392 (3)	C15—H15B	0.9700
C2—C7	1.395 (3)	C16—C15	1.501 (2)
C3—C4	1.395 (3)	C16—C17	1.395 (3)
C3—H3	0.9300	C18—C17	1.390 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C4	1.388 (3)	C19—C18	1.385 (3)
C5—H5	0.9300	C19—C20	1.386 (3)
C6—C5	1.381 (3)	C19—H19	0.9300
C6—H6	0.9300	C21—C16	1.391 (3)
C7—C6	1.385 (3)	C21—C20	1.390 (2)
C7—H7	0.9300	C21—H21	0.9300
C8—H8A	0.9700
C15—O1—C1	111.82 (13)	C9—C10—H10	122.0
N2—N1—C8	120.18 (15)	C11—C10—C9	115.98 (17)
N2—N1—C9	110.27 (14)	C11—C10—H10	122.0
C9—N1—C8	129.53 (15)	C10—C11—C12	122.25 (19)
N3—N2—N1	108.69 (15)	C10—C11—H11	118.9
N2—N3—C14	108.37 (15)	C12—C11—H11	118.9
O1—C1—C2	112.30 (14)	C11—C12—H12	119.2
O1—C1—C8	103.20 (14)	C13—C12—C11	121.54 (19)
O1—C1—H1	109.3	C13—C12—H12	119.2
C2—C1—C8	113.11 (15)	C12—C13—C14	117.29 (17)
C2—C1—H1	109.3	C12—C13—H13	121.4
C8—C1—H1	109.3	C14—C13—H13	121.4
C3—C2—C1	120.21 (16)	N3—C14—C9	108.34 (16)
C3—C2—C7	119.01 (18)	N3—C14—C13	131.14 (17)
C7—C2—C1	120.75 (16)	C9—C14—C13	120.51 (17)
C2—C3—C4	120.57 (19)	O1—C15—C16	109.65 (14)
C2—C3—H3	119.7	O1—C15—H15A	109.7
C4—C3—H3	119.7	O1—C15—H15B	109.7
C3—C4—H4	120.2	C16—C15—H15A	109.7
C5—C4—C3	119.61 (19)	C16—C15—H15B	109.7
C5—C4—H4	120.2	H15A—C15—H15B	108.2
C4—C5—H5	120.0	C17—C16—C15	120.42 (16)
C6—C5—C4	120.05 (19)	C21—C16—C15	121.89 (16)
C6—C5—H5	120.0	C21—C16—C17	117.70 (16)
C5—C6—C7	120.41 (19)	C16—C17—Cl1	118.97 (14)
C5—C6—H6	119.8	C18—C17—Cl1	118.58 (14)
C7—C6—H6	119.8	C18—C17—C16	122.45 (17)
C2—C7—H7	119.8	C17—C18—H18	120.3
C6—C7—C2	120.33 (19)	C19—C18—C17	119.48 (17)
C6—C7—H7	119.8	C19—C18—H18	120.3
N1—C8—C1	112.73 (15)	C18—C19—C20	118.36 (16)
N1—C8—H8A	109.0	C18—C19—H19	120.8
N1—C8—H8B	109.0	C20—C19—H19	120.8
C1—C8—H8A	109.0	C19—C20—Cl2	119.43 (14)
C1—C8—H8B	109.0	C19—C20—C21	122.33 (17)
H8A—C8—H8B	107.8	C21—C20—Cl2	118.22 (14)
N1—C9—C10	133.25 (16)	C16—C21—H21	120.2
N1—C9—C14	104.33 (16)	C20—C21—C16	119.67 (17)
C14—C9—C10	122.42 (18)	C20—C21—H21	120.2
C15—O1—C1—C2	−74.67 (18)	C2—C7—C6—C5	−0.7 (3)
C15—O1—C1—C8	163.19 (14)	N1—C9—C10—C11	179.31 (19)
C1—O1—C15—C16	173.24 (14)	C14—C9—C10—C11	−0.6 (3)
C8—N1—N2—N3	−179.18 (16)	C9—C10—C11—C12	1.1 (3)
C9—N1—N2—N3	−0.7 (2)	C13—C12—C11—C10	−0.9 (3)
N2—N1—C8—C1	81.4 (2)	C14—C13—C12—C11	0.1 (3)
C9—N1—C8—C1	−96.7 (2)	C12—C13—C14—N3	−179.28 (19)
N2—N1—C9—C10	−179.3 (2)	C12—C13—C14—C9	0.4 (3)
N2—N1—C9—C14	0.61 (19)	N3—C14—C9—N1	−0.3 (2)
C8—N1—C9—C10	−1.0 (3)	N3—C14—C9—C10	179.59 (17)
C8—N1—C9—C14	178.92 (17)	C13—C14—C9—N1	179.96 (17)
C14—N3—N2—N1	0.5 (2)	C13—C14—C9—C10	−0.1 (3)
N2—N3—C14—C9	−0.1 (2)	C17—C16—C15—O1	−177.33 (15)
N2—N3—C14—C13	179.59 (19)	C21—C16—C15—O1	2.6 (2)
O1—C1—C8—N1	173.19 (14)	C15—C16—C17—Cl1	0.5 (2)
C2—C1—C8—N1	51.6 (2)	C15—C16—C17—C18	179.99 (17)
C3—C2—C1—O1	139.00 (17)	C21—C16—C17—Cl1	−179.40 (13)
C3—C2—C1—C8	−104.68 (19)	C21—C16—C17—C18	0.1 (3)
C7—C2—C1—O1	−43.0 (2)	C19—C18—C17—Cl1	−179.81 (14)
C7—C2—C1—C8	73.4 (2)	C19—C18—C17—C16	0.7 (3)
C1—C2—C3—C4	177.58 (17)	C20—C19—C18—C17	−1.0 (3)
C7—C2—C3—C4	−0.5 (3)	C18—C19—C20—Cl2	178.73 (14)
C1—C2—C7—C6	−176.83 (17)	C18—C19—C20—C21	0.5 (3)
C3—C2—C7—C6	1.2 (3)	C20—C21—C16—C15	179.49 (16)
C2—C3—C4—C5	−0.8 (3)	C20—C21—C16—C17	−0.6 (3)
C6—C5—C4—C3	1.3 (3)	C16—C21—C20—Cl2	−177.96 (13)
C7—C6—C5—C4	−0.6 (3)	C16—C21—C20—C19	0.3 (3)

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N3i	0.93	2.62	3.549 (2)	174
C18—H18···Cg1ii	0.93	2.69	3.605 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯N3i	0.93	2.62	3.549 (2)	174
C18—H18⋯Cg1ii	0.93	2.69	3.605 (2)	168

Symmetry codes: (i) ; (ii) .