2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol.

In the title compound, C(12)H(11)N(3)O(2), the benzotriazole ring system is approximately planar [maximum deviation = 0.008 (1) Å] and its mean plane is oriented at a dihedral angle of 24.05 (4)° with respect to the furan ring. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into chains along the ac diagonal. π-π stacking between the furan rings, between the triazole and benzene rings, and between the benzene rings [centroid-centroid distances = 3.724 (1), 3.786 (1) and 3.8623 (9) Å] 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: Caira et al. (2004 ▶); Katritzky et al. (2001 ▶); Özel Güven et al. (2008 ▶, 2010 ▶, 2011 ▶); Nanjunda Swamy et al. (2006 ▶).

Experimental

Crystal data

C12H11N3O2

M = 229.24

Monoclinic,

a = 11.3606 (4) Å

b = 11.1034 (4) Å

c = 8.7860 (2) Å

β = 96.938 (2)°

V = 1100.16 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.50 × 0.50 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.953, T max = 0.981

12372 measured reflections

2531 independent reflections

2166 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.139

S = 1.11

2531 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.55 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/S1600536811051798/xu5402sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051798/xu5402Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051798/xu5402Isup3.cml

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

C12H11N3O2	F(000) = 480
Mr = 229.24	Dx = 1.384 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6399 reflections
a = 11.3606 (4) Å	θ = 2.9–27.5°
b = 11.1034 (4) Å	µ = 0.10 mm−1
c = 8.7860 (2) Å	T = 120 K
β = 96.938 (2)°	Block, colorless
V = 1100.16 (6) Å3	0.50 × 0.50 × 0.20 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
Tmin = 0.953, Tmax = 0.981	k = −14→14
12372 measured reflections	l = −10→11

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) = 0.139	w = 1/[σ2(Fo2) + (0.0748P)2 + 0.4779P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2531 reflections	Δρmax = 0.58 e Å−3
155 parameters	Δρmin = −0.55 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: 0.144 (12)

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
O1	0.20677 (10)	0.98199 (10)	0.08354 (12)	0.0223 (3)
H1	0.1559	0.9346	0.1048	0.033*
O2	0.50236 (10)	1.06715 (11)	0.24705 (13)	0.0247 (3)
N1	0.18510 (11)	0.91870 (12)	0.39959 (14)	0.0196 (3)
N2	0.22565 (12)	0.82297 (13)	0.48488 (16)	0.0249 (3)
N3	0.13604 (12)	0.75376 (13)	0.50674 (16)	0.0248 (3)
C1	0.30653 (14)	0.97510 (14)	0.19621 (17)	0.0193 (3)
H1A	0.3392	0.8933	0.1989	0.023*
C2	0.39723 (13)	1.06237 (14)	0.15318 (17)	0.0194 (3)
C3	0.57056 (15)	1.15175 (15)	0.18424 (19)	0.0257 (4)
H3	0.6471	1.1732	0.2247	0.031*
C4	0.51146 (15)	1.19920 (15)	0.05628 (19)	0.0252 (4)
H4	0.5385	1.2581	−0.0062	0.030*
C5	0.39773 (14)	1.14020 (15)	0.03582 (18)	0.0238 (4)
H5	0.3367	1.1533	−0.0429	0.029*
C6	0.26911 (14)	1.00691 (14)	0.35398 (17)	0.0214 (3)
H6A	0.3386	1.0091	0.4298	0.026*
H6B	0.2330	1.0862	0.3496	0.026*
C7	0.06500 (13)	0.91156 (13)	0.36343 (16)	0.0178 (3)
C8	−0.01985 (14)	0.98551 (14)	0.27982 (17)	0.0202 (3)
H8	0.0010	1.0560	0.2326	0.024*
C9	−0.13571 (14)	0.94734 (15)	0.27193 (17)	0.0226 (4)
H9	−0.1949	0.9939	0.2182	0.027*
C10	−0.16792 (14)	0.83958 (15)	0.34283 (17)	0.0232 (4)
H10	−0.2474	0.8174	0.3339	0.028*
C11	−0.08469 (14)	0.76679 (14)	0.42472 (18)	0.0222 (4)
H11	−0.1059	0.6962	0.4713	0.027*
C12	0.03398 (13)	0.80499 (13)	0.43403 (17)	0.0191 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0207 (6)	0.0231 (6)	0.0226 (6)	−0.0047 (4)	0.0004 (4)	−0.0002 (4)
O2	0.0204 (6)	0.0259 (6)	0.0271 (6)	−0.0032 (4)	−0.0001 (4)	0.0002 (4)
N1	0.0181 (6)	0.0205 (6)	0.0205 (6)	0.0001 (5)	0.0030 (5)	0.0020 (5)
N2	0.0224 (7)	0.0249 (7)	0.0272 (7)	0.0045 (5)	0.0023 (5)	0.0044 (5)
N3	0.0231 (7)	0.0221 (7)	0.0293 (7)	0.0043 (5)	0.0038 (5)	0.0059 (6)
C1	0.0204 (7)	0.0172 (7)	0.0203 (7)	−0.0007 (6)	0.0028 (6)	−0.0012 (5)
C2	0.0168 (7)	0.0204 (7)	0.0213 (7)	0.0006 (6)	0.0031 (6)	−0.0038 (6)
C3	0.0203 (8)	0.0251 (8)	0.0322 (8)	−0.0052 (6)	0.0054 (6)	−0.0052 (6)
C4	0.0246 (8)	0.0237 (8)	0.0285 (8)	−0.0047 (6)	0.0087 (6)	−0.0016 (6)
C5	0.0223 (8)	0.0264 (8)	0.0228 (7)	−0.0012 (6)	0.0029 (6)	0.0007 (6)
C6	0.0201 (7)	0.0221 (8)	0.0223 (7)	−0.0039 (6)	0.0041 (6)	−0.0025 (6)
C7	0.0185 (7)	0.0178 (7)	0.0173 (7)	−0.0002 (6)	0.0034 (5)	−0.0017 (5)
C8	0.0248 (8)	0.0178 (7)	0.0184 (7)	0.0020 (6)	0.0040 (6)	0.0030 (5)
C9	0.0213 (8)	0.0274 (8)	0.0185 (7)	0.0056 (6)	0.0002 (6)	−0.0009 (6)
C10	0.0190 (7)	0.0286 (8)	0.0224 (7)	−0.0031 (6)	0.0043 (6)	−0.0042 (6)
C11	0.0243 (8)	0.0191 (8)	0.0244 (8)	−0.0022 (6)	0.0074 (6)	−0.0004 (6)
C12	0.0212 (8)	0.0169 (7)	0.0195 (7)	0.0022 (6)	0.0041 (6)	0.0004 (5)

O1—C1	1.4139 (18)	C4—H4	0.9300
O1—H1	0.8200	C5—C4	1.440 (2)
O2—C2	1.3681 (19)	C5—H5	0.9300
O2—C3	1.375 (2)	C6—H6A	0.9700
N1—N2	1.3492 (18)	C6—H6B	0.9700
N1—C6	1.4571 (19)	C7—C12	1.401 (2)
N1—C7	1.365 (2)	C8—C7	1.404 (2)
N3—N2	1.308 (2)	C8—C9	1.376 (2)
N3—C12	1.377 (2)	C8—H8	0.9300
C1—C6	1.539 (2)	C9—H9	0.9300
C1—H1A	0.9800	C10—C9	1.417 (2)
C2—C1	1.496 (2)	C10—H10	0.9300
C2—C5	1.346 (2)	C11—C10	1.379 (2)
C3—C4	1.345 (2)	C11—C12	1.406 (2)
C3—H3	0.9300	C11—H11	0.9300
C1—O1—H1	109.5	N1—C6—C1	110.77 (12)
C2—O2—C3	106.13 (12)	N1—C6—H6A	109.5
N2—N1—C7	110.36 (12)	N1—C6—H6B	109.5
N2—N1—C6	119.43 (12)	C1—C6—H6A	109.5
C7—N1—C6	130.13 (13)	C1—C6—H6B	109.5
N3—N2—N1	108.96 (13)	H6A—C6—H6B	108.1
N2—N3—C12	108.40 (13)	N1—C7—C8	133.73 (14)
O1—C1—C2	107.84 (12)	N1—C7—C12	104.11 (13)
O1—C1—C6	109.45 (12)	C12—C7—C8	122.15 (14)
O1—C1—H1A	109.6	C7—C8—H8	122.0
C2—C1—C6	110.64 (12)	C9—C8—C7	115.98 (14)
C2—C1—H1A	109.6	C9—C8—H8	122.0
C6—C1—H1A	109.6	C8—C9—C10	122.27 (15)
O2—C2—C1	116.78 (13)	C8—C9—H9	118.9
C5—C2—O2	110.66 (14)	C10—C9—H9	118.9
C5—C2—C1	132.56 (14)	C9—C10—H10	119.1
O2—C3—H3	124.6	C11—C10—C9	121.81 (15)
C4—C3—O2	110.75 (14)	C11—C10—H10	119.1
C4—C3—H3	124.6	C10—C11—C12	116.47 (14)
C3—C4—C5	106.01 (14)	C10—C11—H11	121.8
C3—C4—H4	127.0	C12—C11—H11	121.8
C5—C4—H4	127.0	N3—C12—C7	108.16 (13)
C2—C5—C4	106.45 (14)	N3—C12—C11	130.53 (15)
C2—C5—H5	126.8	C7—C12—C11	121.31 (14)
C4—C5—H5	126.8
C6—N1—N2—N3	−177.41 (13)	C5—C2—C1—O1	0.9 (2)
C7—N1—N2—N3	−0.44 (17)	C5—C2—C1—C6	−118.73 (19)
N2—N1—C6—C1	92.27 (16)	O2—C2—C5—C4	−0.09 (18)
C7—N1—C6—C1	−84.02 (19)	C1—C2—C5—C4	−179.58 (15)
N2—N1—C7—C8	179.68 (16)	O2—C3—C4—C5	−0.27 (18)
N2—N1—C7—C12	0.62 (16)	C2—C5—C4—C3	0.21 (18)
C6—N1—C7—C8	−3.8 (3)	N1—C7—C12—N3	−0.58 (16)
C6—N1—C7—C12	177.17 (14)	N1—C7—C12—C11	179.06 (14)
C12—N3—N2—N1	0.05 (17)	C8—C7—C12—N3	−179.77 (13)
N2—N3—C12—C7	0.34 (17)	C8—C7—C12—C11	−0.1 (2)
N2—N3—C12—C11	−179.25 (15)	C9—C8—C7—N1	−178.60 (15)
C3—O2—C2—C1	179.51 (13)	C9—C8—C7—C12	0.3 (2)
C3—O2—C2—C5	−0.07 (17)	C7—C8—C9—C10	−0.4 (2)
C2—O2—C3—C4	0.22 (18)	C11—C10—C9—C8	0.3 (2)
O1—C1—C6—N1	64.08 (16)	C10—C11—C12—N3	179.57 (15)
C2—C1—C6—N1	−177.23 (12)	C10—C11—C12—C7	0.0 (2)
O2—C2—C1—O1	−178.53 (12)	C12—C11—C10—C9	−0.1 (2)
O2—C2—C1—C6	61.80 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.82	2.26	2.7968 (18)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.82	2.26	2.7968 (18)	123

Symmetry code: (i) .