1-[2-(2,4-Dichloro-benz-yloxy)-2-(furan-2-yl)eth-yl]-1H-benzotriazole.

In the title compound, C(19)H(15)Cl(2)N(3)O(2), the benzotriazole ring system is approximately planar [maximum deviation = 0.018 (2) Å] and its mean plane is oriented at dihedral angles of 30.70 (5) and 87.38 (4)°, respectively, to the furan and benzene rings while the dihedral angle between furan and benzene rings is 74.46 (6)°. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into chains along the b axis. π-π stacking inter-actions between the parallel dichloro-benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.6847 (9) Å] and weak C-H⋯π inter-actions 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 ▶); Özel Güven et al. (2007a ▶,b ▶); Peeters et al. (1979 ▶); Freer et al. (1986 ▶). For related structures, see: Özel Güven et al. (2008 ▶, 2009 ▶, 2010a ▶,b ▶, 2011 ▶. For the synthesis of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanol, see: Özel Güven et al. (2012 ▶).

Experimental

Crystal data

C19H15Cl2N3O2

M = 388.24

Monoclinic,

a = 11.5452 (2) Å

b = 20.0350 (5) Å

c = 8.3317 (2) Å

β = 105.598 (2)°

V = 1856.21 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 120 K

0.50 × 0.30 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.837, T max = 0.971

31461 measured reflections

4251 independent reflections

3252 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.04

4251 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.34 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/S1600536811053104/xu5406sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053104/xu5406Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053104/xu5406Isup3.cml

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

C19H15Cl2N3O2	F(000) = 800
Mr = 388.24	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11553 reflections
a = 11.5452 (2) Å	θ = 2.9–27.5°
b = 20.0350 (5) Å	µ = 0.37 mm−1
c = 8.3317 (2) Å	T = 120 K
β = 105.598 (2)°	Slab, colorless
V = 1856.21 (7) Å3	0.50 × 0.30 × 0.08 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	4251 independent reflections
Radiation source: fine-focus sealed tube	3252 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 27.6°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
Tmin = 0.837, Tmax = 0.971	k = −26→26
31461 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.507P] where P = (Fo2 + 2Fc2)/3
4251 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.34 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	0.89226 (4)	0.18886 (2)	0.01379 (7)	0.04089 (16)
Cl2	1.28141 (4)	0.02933 (3)	0.12097 (6)	0.03513 (14)
O1	0.75307 (10)	0.03838 (5)	0.30260 (14)	0.0220 (3)
O2	0.66612 (11)	0.09918 (6)	0.57356 (14)	0.0268 (3)
N1	0.60882 (12)	−0.07713 (7)	0.26337 (16)	0.0203 (3)
N2	0.51947 (12)	−0.09229 (7)	0.12492 (17)	0.0243 (3)
N3	0.55075 (13)	−0.14513 (7)	0.05429 (18)	0.0256 (3)
C1	0.62928 (14)	0.04521 (8)	0.3022 (2)	0.0207 (3)
H1	0.5806	0.0518	0.1873	0.025*
C2	0.60997 (14)	0.10283 (8)	0.4057 (2)	0.0210 (3)
C3	0.63944 (16)	0.15769 (9)	0.6416 (2)	0.0291 (4)
H3	0.6660	0.1687	0.7540	0.035*
C4	0.57008 (18)	0.19676 (9)	0.5242 (2)	0.0335 (4)
H4	0.5407	0.2388	0.5395	0.040*
C5	0.55017 (17)	0.16100 (9)	0.3709 (2)	0.0320 (4)
H5	0.5046	0.1752	0.2668	0.038*
C6	0.59430 (14)	−0.02090 (8)	0.3666 (2)	0.0209 (3)
H6A	0.6437	−0.0281	0.4794	0.025*
H6B	0.5111	−0.0186	0.3701	0.025*
C7	0.70139 (14)	−0.12118 (8)	0.28229 (19)	0.0190 (3)
C8	0.81400 (14)	−0.12713 (8)	0.3997 (2)	0.0227 (3)
H8	0.8386	−0.0980	0.4894	0.027*
C9	0.88576 (16)	−0.17884 (8)	0.3736 (2)	0.0258 (4)
H9	0.9616	−0.1843	0.4470	0.031*
C10	0.84755 (16)	−0.22394 (8)	0.2385 (2)	0.0275 (4)
H10	0.8986	−0.2584	0.2265	0.033*
C11	0.73701 (16)	−0.21804 (8)	0.1249 (2)	0.0266 (4)
H11	0.7121	−0.2478	0.0367	0.032*
C12	0.66331 (15)	−0.16504 (8)	0.1477 (2)	0.0214 (3)
C13	0.79095 (15)	0.09078 (8)	0.2133 (2)	0.0251 (4)
H13A	0.7933	0.1326	0.2729	0.030*
H13B	0.7345	0.0956	0.1043	0.030*
C14	0.91411 (14)	0.07481 (8)	0.1944 (2)	0.0207 (3)
C15	0.96919 (15)	0.11711 (8)	0.1043 (2)	0.0250 (4)
C16	1.08124 (15)	0.10456 (9)	0.0812 (2)	0.0269 (4)
H16	1.1158	0.1338	0.0207	0.032*
C17	1.14060 (14)	0.04695 (9)	0.1510 (2)	0.0242 (4)
C18	1.09010 (15)	0.00307 (8)	0.2414 (2)	0.0238 (4)
H18	1.1309	−0.0354	0.2874	0.029*
C19	0.97711 (15)	0.01756 (8)	0.2619 (2)	0.0228 (4)
H19	0.9427	−0.0118	0.3223	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0253 (3)	0.0312 (3)	0.0594 (3)	−0.00467 (18)	−0.0003 (2)	0.0213 (2)
Cl2	0.0204 (2)	0.0536 (3)	0.0334 (3)	−0.00010 (18)	0.01082 (18)	0.0020 (2)
O1	0.0185 (6)	0.0211 (6)	0.0288 (6)	0.0031 (4)	0.0106 (5)	0.0030 (5)
O2	0.0287 (7)	0.0240 (6)	0.0246 (6)	0.0066 (5)	0.0017 (5)	−0.0029 (5)
N1	0.0196 (7)	0.0203 (7)	0.0211 (7)	−0.0007 (5)	0.0057 (5)	−0.0026 (5)
N2	0.0227 (7)	0.0253 (7)	0.0242 (7)	−0.0021 (6)	0.0053 (6)	−0.0028 (6)
N3	0.0268 (8)	0.0248 (7)	0.0251 (8)	−0.0028 (6)	0.0070 (6)	−0.0032 (6)
C1	0.0183 (8)	0.0209 (8)	0.0231 (8)	0.0027 (6)	0.0061 (6)	−0.0021 (7)
C2	0.0182 (8)	0.0234 (8)	0.0207 (8)	0.0019 (6)	0.0043 (6)	−0.0007 (7)
C3	0.0329 (10)	0.0261 (9)	0.0274 (9)	0.0007 (7)	0.0066 (8)	−0.0091 (7)
C4	0.0404 (11)	0.0246 (9)	0.0357 (11)	0.0114 (8)	0.0107 (9)	−0.0035 (8)
C5	0.0408 (11)	0.0299 (10)	0.0229 (9)	0.0132 (8)	0.0041 (8)	0.0007 (8)
C6	0.0209 (8)	0.0208 (8)	0.0228 (8)	0.0010 (6)	0.0092 (6)	−0.0038 (7)
C7	0.0219 (8)	0.0166 (8)	0.0205 (8)	−0.0010 (6)	0.0093 (6)	0.0019 (6)
C8	0.0240 (9)	0.0208 (8)	0.0228 (8)	−0.0010 (6)	0.0057 (7)	0.0001 (7)
C9	0.0243 (9)	0.0244 (9)	0.0290 (9)	0.0029 (7)	0.0073 (7)	0.0045 (7)
C10	0.0328 (10)	0.0222 (9)	0.0310 (10)	0.0056 (7)	0.0147 (8)	0.0033 (7)
C11	0.0363 (10)	0.0190 (8)	0.0274 (9)	−0.0010 (7)	0.0136 (8)	−0.0027 (7)
C12	0.0246 (9)	0.0196 (8)	0.0211 (8)	−0.0030 (6)	0.0079 (7)	−0.0011 (7)
C13	0.0263 (9)	0.0172 (8)	0.0336 (10)	0.0007 (6)	0.0112 (7)	0.0038 (7)
C14	0.0199 (8)	0.0186 (8)	0.0231 (8)	−0.0032 (6)	0.0047 (6)	−0.0034 (6)
C15	0.0224 (9)	0.0235 (9)	0.0260 (9)	−0.0042 (7)	0.0010 (7)	0.0037 (7)
C16	0.0229 (9)	0.0326 (9)	0.0251 (9)	−0.0103 (7)	0.0060 (7)	0.0035 (7)
C17	0.0179 (8)	0.0336 (9)	0.0211 (8)	−0.0049 (7)	0.0054 (6)	−0.0052 (7)
C18	0.0226 (8)	0.0238 (8)	0.0249 (9)	0.0004 (7)	0.0063 (7)	−0.0022 (7)
C19	0.0234 (9)	0.0203 (8)	0.0254 (9)	−0.0016 (6)	0.0077 (7)	0.0017 (7)

Cl1—C15	1.7504 (17)	C7—C8	1.406 (2)
Cl2—C17	1.7461 (17)	C7—C12	1.399 (2)
O1—C1	1.4348 (18)	C8—C9	1.380 (2)
O1—C13	1.4220 (19)	C8—H8	0.9300
O2—C2	1.376 (2)	C9—H9	0.9300
O2—C3	1.373 (2)	C10—C9	1.418 (3)
N1—C6	1.454 (2)	C10—H10	0.9300
N1—C7	1.362 (2)	C11—C10	1.375 (2)
N2—N1	1.3591 (18)	C11—H11	0.9300
N2—N3	1.3084 (19)	C12—C11	1.405 (2)
N3—C12	1.382 (2)	C13—H13A	0.9700
C1—C2	1.493 (2)	C13—H13B	0.9700
C1—C6	1.524 (2)	C14—C13	1.506 (2)
C1—H1	0.9800	C14—C15	1.394 (2)
C2—C5	1.346 (2)	C14—C19	1.393 (2)
C3—C4	1.338 (3)	C15—C16	1.381 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—H4	0.9300	C17—C16	1.388 (2)
C5—C4	1.429 (3)	C17—C18	1.384 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—H6A	0.9700	C19—C18	1.391 (2)
C6—H6B	0.9700	C19—H19	0.9300
C13—O1—C1	112.00 (12)	C8—C9—C10	122.12 (17)
C3—O2—C2	106.11 (13)	C8—C9—H9	118.9
N2—N1—C6	119.55 (13)	C10—C9—H9	118.9
N2—N1—C7	110.26 (13)	C9—C10—H10	119.2
C7—N1—C6	130.18 (13)	C11—C10—C9	121.67 (16)
N3—N2—N1	108.92 (13)	C11—C10—H10	119.2
N2—N3—C12	108.15 (13)	C10—C11—C12	117.10 (16)
O1—C1—C2	112.06 (13)	C10—C11—H11	121.4
O1—C1—C6	105.93 (12)	C12—C11—H11	121.4
O1—C1—H1	108.9	N3—C12—C7	108.39 (14)
C2—C1—C6	111.94 (13)	N3—C12—C11	130.82 (15)
C2—C1—H1	108.9	C7—C12—C11	120.78 (15)
C6—C1—H1	108.9	O1—C13—C14	109.25 (13)
O2—C2—C1	116.31 (13)	O1—C13—H13A	109.8
C5—C2—O2	109.84 (14)	O1—C13—H13B	109.8
C5—C2—C1	133.82 (16)	C14—C13—H13A	109.8
O2—C3—H3	124.6	C14—C13—H13B	109.8
C4—C3—O2	110.77 (16)	H13A—C13—H13B	108.3
C4—C3—H3	124.6	C15—C14—C13	120.49 (15)
C3—C4—C5	106.32 (15)	C19—C14—C13	122.53 (15)
C3—C4—H4	126.8	C19—C14—C15	116.98 (15)
C5—C4—H4	126.8	C14—C15—Cl1	118.63 (13)
C2—C5—C4	106.96 (16)	C16—C15—Cl1	118.37 (13)
C2—C5—H5	126.5	C16—C15—C14	122.99 (16)
C4—C5—H5	126.5	C15—C16—C17	117.93 (15)
N1—C6—C1	112.43 (13)	C15—C16—H16	121.0
N1—C6—H6A	109.1	C17—C16—H16	121.0
N1—C6—H6B	109.1	C16—C17—Cl2	118.82 (13)
C1—C6—H6A	109.1	C18—C17—Cl2	119.61 (14)
C1—C6—H6B	109.1	C18—C17—C16	121.57 (16)
H6A—C6—H6B	107.9	C17—C18—C19	118.72 (16)
N1—C7—C12	104.27 (14)	C17—C18—H18	120.6
N1—C7—C8	133.26 (15)	C19—C18—H18	120.6
C12—C7—C8	122.47 (15)	C14—C19—H19	119.1
C7—C8—H8	122.1	C18—C19—C14	121.81 (16)
C9—C8—C7	115.84 (15)	C18—C19—H19	119.1
C9—C8—H8	122.1
C13—O1—C1—C2	−69.97 (17)	N1—C7—C12—N3	0.40 (17)
C13—O1—C1—C6	167.70 (13)	N1—C7—C8—C9	−178.39 (17)
C1—O1—C13—C14	−170.80 (13)	C12—C7—C8—C9	0.5 (2)
C3—O2—C2—C1	177.97 (14)	N1—C7—C12—C11	179.67 (15)
C3—O2—C2—C5	−0.38 (19)	C8—C7—C12—N3	−178.76 (14)
C2—O2—C3—C4	0.0 (2)	C8—C7—C12—C11	0.5 (2)
N2—N1—C6—C1	−84.26 (17)	C7—C8—C9—C10	−1.1 (2)
C7—N1—C6—C1	96.81 (19)	C11—C10—C9—C8	0.7 (3)
N2—N1—C7—C8	178.45 (16)	C12—C11—C10—C9	0.3 (2)
N2—N1—C7—C12	−0.58 (17)	N3—C12—C11—C10	178.19 (16)
C6—N1—C7—C8	−2.5 (3)	C7—C12—C11—C10	−0.9 (2)
C6—N1—C7—C12	178.42 (15)	C15—C14—C13—O1	177.03 (15)
N3—N2—N1—C6	−178.57 (13)	C19—C14—C13—O1	−1.8 (2)
N3—N2—N1—C7	0.56 (17)	C13—C14—C15—Cl1	−0.1 (2)
N1—N2—N3—C12	−0.28 (17)	C13—C14—C15—C16	−179.17 (16)
N2—N3—C12—C7	−0.08 (18)	C19—C14—C15—Cl1	178.80 (13)
N2—N3—C12—C11	−179.25 (17)	C19—C14—C15—C16	−0.3 (3)
O1—C1—C2—O2	−63.48 (18)	C13—C14—C19—C18	179.09 (15)
O1—C1—C2—C5	114.4 (2)	C15—C14—C19—C18	0.2 (2)
C6—C1—C2—O2	55.36 (18)	Cl1—C15—C16—C17	−178.90 (13)
C6—C1—C2—C5	−126.8 (2)	C14—C15—C16—C17	0.2 (3)
O1—C1—C6—N1	−59.57 (16)	Cl2—C17—C16—C15	179.06 (13)
C2—C1—C6—N1	178.02 (13)	C18—C17—C16—C15	0.0 (3)
O2—C2—C5—C4	0.6 (2)	Cl2—C17—C18—C19	−179.11 (12)
C1—C2—C5—C4	−177.35 (18)	C16—C17—C18—C19	0.0 (3)
O2—C3—C4—C5	0.4 (2)	C14—C19—C18—C17	−0.1 (3)
C2—C5—C4—C3	−0.6 (2)

Cg is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N3i	0.93	2.59	3.452 (2)	155
C8—H8···Cgii	0.93	2.92	3.782 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N3i	0.93	2.59	3.452 (2)	155
C8—H8⋯Cgii	0.93	2.92	3.782 (2)	155

Symmetry codes: (i) ; (ii) .