2-[4-(2-Hy-droxy-propan-2-yl)-1H-1,2,3-triazol-1-yl]phenol.

In the title compound, C(11)H(13)N(3)O(2), the 1,2,3-triazole ring and the phenol ring form a dihedral angle of 55.46 (5)°. In the crystal, inversion-related mol-ecules associate through pairs of hy-droxy-phenol O-H⋯O hydrogen bonds, giving centrosymmetric cyclic dimers [graph set R(2) (2)(18)]. These dimers are linked into infinite chains along [001], giving an overall two-dimensional network structure parallel to the bc plane through hy-droxy O-H⋯N and triazole C-H⋯N hydrogen bonds.

Related literature

For general background to 1,2,3-triazole derivatives, see: Shia et al. (2002 ▶); Orgueira et al. (2005 ▶); Crowley & Bandeen (2010 ▶). For related structures, see: Zou et al. (2006 ▶); Danielraj et al. (2010 ▶); Stöger et al. (2011 ▶). For bond-length data, see: Banerjee et al. (2002 ▶); Janas & Sobota (2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H13N3O2

M = 219.24

Monoclinic,

a = 11.599 (2) Å

b = 9.0747 (18) Å

c = 10.743 (2) Å

β = 107.081 (3)°

V = 1080.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.40 × 0.30 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.963, T max = 0.983

5462 measured reflections

1994 independent reflections

1696 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.05

1994 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012925/zs2192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012925/zs2192Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012925/zs2192Isup3.cml

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

C11H13N3O2	F(000) = 464
Mr = 219.24	Dx = 1.347 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2071 reflections
a = 11.599 (2) Å	θ = 2.9–23.0°
b = 9.0747 (18) Å	µ = 0.10 mm−1
c = 10.743 (2) Å	T = 298 K
β = 107.081 (3)°	Block, pale yellow
V = 1080.9 (3) Å3	0.40 × 0.30 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1994 independent reflections
Radiation source: fine-focus sealed tube	1696 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −14→12
Tmin = 0.963, Tmax = 0.983	k = −10→10
5462 measured reflections	l = −11→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1715P] where P = (Fo2 + 2Fc2)/3
1994 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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	0.57130 (10)	0.27595 (13)	0.05416 (11)	0.0285 (3)
N2	0.50492 (12)	0.30872 (16)	−0.06770 (11)	0.0374 (3)
N3	0.39371 (11)	0.32767 (15)	−0.06404 (11)	0.0352 (3)
O1	0.26044 (9)	0.18448 (11)	0.16529 (9)	0.0321 (3)
H1	0.2976	0.1914	0.2428	0.048*
O2	0.65112 (10)	0.05481 (13)	−0.07335 (11)	0.0447 (3)
H2	0.6832	−0.0144	−0.0993	0.067*
C1	0.93917 (15)	0.1799 (2)	0.14569 (17)	0.0443 (4)
H1A	1.0210	0.1584	0.1663	0.053*
C2	0.90012 (16)	0.2893 (2)	0.21198 (17)	0.0478 (5)
H2A	0.9552	0.3409	0.2780	0.057*
C3	0.77857 (14)	0.32227 (18)	0.18018 (15)	0.0391 (4)
H3	0.7517	0.3971	0.2239	0.047*
C4	0.69727 (13)	0.24373 (16)	0.08337 (13)	0.0293 (3)
C5	0.73520 (13)	0.13098 (17)	0.01699 (14)	0.0314 (4)
C6	0.85794 (14)	0.10189 (19)	0.04891 (15)	0.0389 (4)
H6	0.8857	0.0287	0.0043	0.047*
C7	0.50258 (13)	0.27627 (17)	0.13542 (13)	0.0312 (4)
H7	0.5273	0.2581	0.2245	0.037*
C8	0.38921 (13)	0.30876 (15)	0.05978 (13)	0.0276 (3)
C9	0.27444 (13)	0.32016 (16)	0.09872 (14)	0.0312 (4)
C10	0.28121 (17)	0.44984 (19)	0.18952 (18)	0.0495 (5)
H10A	0.2095	0.4530	0.2167	0.074*
H10B	0.2881	0.5396	0.1449	0.074*
H10C	0.3503	0.4391	0.2645	0.074*
C11	0.16508 (15)	0.3294 (2)	−0.01930 (17)	0.0495 (5)
H11A	0.1618	0.2438	−0.0727	0.074*
H11B	0.1704	0.4162	−0.0684	0.074*
H11C	0.0935	0.3341	0.0082	0.074*

	U11	U22	U33	U12	U13	U23
N1	0.0282 (6)	0.0342 (7)	0.0230 (6)	0.0021 (5)	0.0074 (5)	0.0005 (5)
N2	0.0356 (7)	0.0538 (9)	0.0229 (6)	0.0069 (6)	0.0088 (5)	0.0035 (6)
N3	0.0327 (7)	0.0475 (8)	0.0254 (6)	0.0055 (6)	0.0083 (5)	0.0012 (6)
O1	0.0347 (6)	0.0357 (6)	0.0252 (5)	−0.0038 (4)	0.0077 (4)	−0.0015 (4)
O2	0.0401 (7)	0.0444 (7)	0.0469 (7)	0.0023 (5)	0.0084 (5)	−0.0152 (5)
C1	0.0284 (8)	0.0522 (11)	0.0519 (10)	0.0023 (7)	0.0114 (8)	0.0061 (8)
C2	0.0364 (10)	0.0517 (11)	0.0479 (10)	−0.0050 (8)	0.0010 (8)	−0.0062 (8)
C3	0.0380 (9)	0.0414 (9)	0.0358 (9)	0.0011 (7)	0.0079 (7)	−0.0057 (7)
C4	0.0293 (8)	0.0325 (8)	0.0276 (7)	0.0014 (6)	0.0106 (6)	0.0045 (6)
C5	0.0317 (8)	0.0341 (8)	0.0291 (8)	−0.0019 (6)	0.0100 (6)	0.0018 (6)
C6	0.0376 (9)	0.0413 (9)	0.0422 (9)	0.0056 (7)	0.0187 (7)	0.0014 (7)
C7	0.0326 (8)	0.0404 (9)	0.0218 (7)	0.0003 (6)	0.0098 (6)	0.0011 (6)
C8	0.0324 (8)	0.0276 (8)	0.0224 (7)	−0.0006 (6)	0.0077 (6)	−0.0024 (6)
C9	0.0309 (8)	0.0322 (8)	0.0319 (8)	0.0018 (6)	0.0113 (6)	0.0025 (6)
C10	0.0594 (12)	0.0372 (10)	0.0632 (12)	0.0013 (8)	0.0355 (10)	−0.0056 (8)
C11	0.0327 (9)	0.0685 (13)	0.0466 (10)	0.0057 (8)	0.0107 (8)	0.0180 (9)

N1—N2	1.3428 (16)	C3—H3	0.9300
N1—C7	1.3441 (18)	C4—C5	1.390 (2)
N1—C4	1.4316 (19)	C5—C6	1.388 (2)
N2—N3	1.3134 (18)	C6—H6	0.9300
N3—C8	1.3575 (18)	C7—C8	1.360 (2)
O1—C9	1.4568 (18)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.512 (2)
O2—C5	1.3472 (18)	C9—C11	1.510 (2)
O2—H2	0.8200	C9—C10	1.516 (2)
C1—C2	1.374 (3)	C10—H10A	0.9600
C1—C6	1.376 (2)	C10—H10B	0.9600
C1—H1A	0.9300	C10—H10C	0.9600
C2—C3	1.383 (2)	C11—H11A	0.9600
C2—H2A	0.9300	C11—H11B	0.9600
C3—C4	1.379 (2)	C11—H11C	0.9600
N2—N1—C7	110.68 (12)	N1—C7—C8	105.44 (12)
N2—N1—C4	121.00 (11)	N1—C7—H7	127.3
C7—N1—C4	128.31 (12)	C8—C7—H7	127.3
N3—N2—N1	106.67 (11)	N3—C8—C7	107.72 (13)
N2—N3—C8	109.48 (12)	N3—C8—C9	123.57 (13)
C9—O1—H1	109.5	C7—C8—C9	128.70 (13)
C5—O2—H2	109.5	O1—C9—C11	105.78 (12)
C2—C1—C6	120.43 (15)	O1—C9—C8	108.19 (11)
C2—C1—H1A	119.8	C11—C9—C8	111.25 (12)
C6—C1—H1A	119.8	O1—C9—C10	109.42 (12)
C1—C2—C3	119.74 (16)	C11—C9—C10	111.68 (14)
C1—C2—H2A	120.1	C8—C9—C10	110.36 (13)
C3—C2—H2A	120.1	C9—C10—H10A	109.5
C4—C3—C2	119.74 (15)	C9—C10—H10B	109.5
C4—C3—H3	120.1	H10A—C10—H10B	109.5
C2—C3—H3	120.1	C9—C10—H10C	109.5
C3—C4—C5	121.17 (14)	H10A—C10—H10C	109.5
C3—C4—N1	119.17 (13)	H10B—C10—H10C	109.5
C5—C4—N1	119.62 (13)	C9—C11—H11A	109.5
O2—C5—C6	123.59 (14)	C9—C11—H11B	109.5
O2—C5—C4	118.42 (13)	H11A—C11—H11B	109.5
C6—C5—C4	117.99 (14)	C9—C11—H11C	109.5
C1—C6—C5	120.90 (15)	H11A—C11—H11C	109.5
C1—C6—H6	119.5	H11B—C11—H11C	109.5
C5—C6—H6	119.5
C7—N1—N2—N3	−0.92 (17)	C2—C1—C6—C5	−0.6 (3)
C4—N1—N2—N3	177.94 (12)	O2—C5—C6—C1	−177.47 (15)
N1—N2—N3—C8	0.68 (16)	C4—C5—C6—C1	1.6 (2)
C6—C1—C2—C3	−0.7 (3)	N2—N1—C7—C8	0.77 (16)
C1—C2—C3—C4	0.9 (3)	C4—N1—C7—C8	−177.98 (14)
C2—C3—C4—C5	0.2 (2)	N2—N3—C8—C7	−0.22 (17)
C2—C3—C4—N1	178.08 (14)	N2—N3—C8—C9	−178.97 (13)
N2—N1—C4—C3	125.90 (15)	N1—C7—C8—N3	−0.34 (16)
C7—N1—C4—C3	−55.5 (2)	N1—C7—C8—C9	178.33 (14)
N2—N1—C4—C5	−56.22 (19)	N3—C8—C9—O1	125.29 (14)
C7—N1—C4—C5	122.42 (16)	C7—C8—C9—O1	−53.19 (19)
C3—C4—C5—O2	177.68 (14)	N3—C8—C9—C11	9.5 (2)
N1—C4—C5—O2	−0.2 (2)	C7—C8—C9—C11	−168.97 (16)
C3—C4—C5—C6	−1.5 (2)	N3—C8—C9—C10	−115.03 (16)
N1—C4—C5—C6	−179.33 (13)	C7—C8—C9—C10	66.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.89	2.7090 (15)	173
O1—H1···N3ii	0.82	2.05	2.8665 (16)	171
C7—H7···N2ii	0.93	2.40	3.2738 (19)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.89	2.7090 (15)	173
O1—H1⋯N3ii	0.82	2.05	2.8665 (16)	171
C7—H7⋯N2ii	0.93	2.40	3.2738 (19)	157

Symmetry codes: (i) ; (ii) .