1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol.

In the title compound, C(10)H(11)N(3)O, the planar five- and six-membered rings are nearly parallel to each other, making a dihedral angle of 2.52 (5)°. Weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers and strong inter-molecular O-H⋯N hydrogen bonds link the dimers into infinite chains along the b axis.

Related literature

For general backgroud, see: Holla et al. (1996 ▶); Sengupta et al. (1978 ▶); Paulvannan et al. (2001 ▶); Sui et al. (1998 ▶); Bodey (1992 ▶). For related literature, see: Peeters et al. (1979a ▶,b ▶); Caira et al. (2004 ▶); Freer et al. (1986 ▶); Peeters et al. (1996 ▶).

Experimental

Crystal data

C10H11N3O

M = 189.22

Monoclinic,

a = 11.5356 (2) Å

b = 10.1173 (2) Å

c = 8.7127 (2) Å

β = 108.581 (1)°

V = 963.85 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.55 × 0.25 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.972, T max = 0.989

13352 measured reflections

2208 independent reflections

1647 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.03

2208 reflections

171 parameters

All H-atom parameters refined

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXL97 (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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017303/fl2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017303/fl2201Isup2.hkl

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

C10H11N3O	F000 = 400
Mr = 189.22	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12727 reflections
a = 11.5356 (2) Å	θ = 2.9–27.5º
b = 10.1173 (2) Å	µ = 0.09 mm−1
c = 8.7127 (2) Å	T = 294 (2) K
β = 108.581 (1)º	Block, colorless
V = 963.85 (3) Å3	0.55 × 0.25 × 0.10 mm
Z = 4

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2208 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1647 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.2º
φ and ω scans	h = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −13→12
Tmin = 0.972, Tmax = 0.989	l = −11→10
13352 measured reflections

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)] = 0.042	All H-atom parameters refined
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1287P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2208 reflections	Δρmax = 0.16 e Å−3
171 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O	0.87872 (10)	0.13609 (12)	0.06628 (11)	0.0588 (3)
H	0.813 (2)	0.182 (2)	0.013 (3)	0.096 (7)*
N1	0.72669 (9)	0.10513 (11)	0.27992 (13)	0.0434 (3)
N2	0.68815 (10)	0.20410 (13)	0.35760 (14)	0.0521 (3)
N3	0.52850 (11)	0.11273 (16)	0.16751 (19)	0.0727 (4)
C1	0.56896 (13)	0.20320 (19)	0.2849 (2)	0.0630 (4)
H1	0.5169 (17)	0.2639 (19)	0.316 (2)	0.081 (6)*
C2	0.63083 (13)	0.05341 (18)	0.1683 (2)	0.0596 (4)
H2	0.6363 (16)	−0.0179 (19)	0.098 (2)	0.074 (5)*
C3	0.85650 (11)	0.07494 (15)	0.32125 (17)	0.0445 (3)
H31	0.8629 (14)	−0.0199 (17)	0.288 (2)	0.063 (5)*
H32	0.8938 (14)	0.0825 (15)	0.439 (2)	0.059 (4)*
C4	0.91941 (11)	0.16584 (13)	0.23363 (14)	0.0376 (3)
H4	0.8978 (11)	0.2558 (13)	0.2499 (15)	0.034 (3)*
C5	1.05661 (10)	0.14872 (12)	0.30176 (14)	0.0354 (3)
C6	1.12425 (12)	0.22987 (15)	0.42648 (16)	0.0480 (3)
H6	1.0823 (15)	0.2996 (17)	0.467 (2)	0.070 (5)*
C7	1.24947 (13)	0.21333 (16)	0.49370 (19)	0.0572 (4)
H7	1.2961 (16)	0.2732 (19)	0.584 (2)	0.079 (5)*
C8	1.30805 (13)	0.11523 (17)	0.4370 (2)	0.0566 (4)
H8	1.3973 (17)	0.1018 (18)	0.484 (2)	0.078 (5)*
C9	1.24185 (13)	0.03446 (15)	0.31286 (19)	0.0529 (4)
H9	1.2826 (15)	−0.0328 (17)	0.269 (2)	0.065 (5)*
C10	1.11643 (12)	0.05072 (13)	0.24487 (16)	0.0426 (3)
H10	1.0711 (14)	−0.0032 (15)	0.1553 (19)	0.055 (4)*

	U11	U22	U33	U12	U13	U23
O	0.0489 (6)	0.0914 (8)	0.0316 (5)	0.0183 (6)	0.0065 (4)	0.0033 (5)
N1	0.0314 (5)	0.0530 (6)	0.0427 (6)	−0.0020 (4)	0.0077 (5)	0.0030 (5)
N2	0.0371 (6)	0.0646 (8)	0.0512 (7)	−0.0016 (5)	0.0095 (5)	−0.0048 (6)
N3	0.0349 (6)	0.0949 (11)	0.0780 (10)	−0.0047 (7)	0.0036 (6)	−0.0166 (8)
C1	0.0365 (7)	0.0801 (11)	0.0692 (10)	0.0026 (7)	0.0124 (7)	−0.0067 (9)
C2	0.0399 (8)	0.0711 (10)	0.0607 (9)	−0.0100 (7)	0.0061 (7)	−0.0121 (8)
C3	0.0321 (6)	0.0542 (8)	0.0438 (7)	0.0021 (5)	0.0075 (5)	0.0098 (6)
C4	0.0363 (6)	0.0399 (7)	0.0345 (6)	0.0042 (5)	0.0084 (5)	0.0021 (5)
C5	0.0347 (6)	0.0380 (6)	0.0345 (6)	−0.0004 (5)	0.0122 (5)	0.0041 (5)
C6	0.0440 (7)	0.0515 (8)	0.0465 (7)	−0.0005 (6)	0.0116 (6)	−0.0084 (6)
C7	0.0441 (8)	0.0671 (10)	0.0537 (8)	−0.0100 (7)	0.0060 (6)	−0.0084 (8)
C8	0.0337 (7)	0.0728 (10)	0.0603 (9)	0.0009 (7)	0.0106 (6)	0.0085 (8)
C9	0.0456 (8)	0.0579 (9)	0.0585 (8)	0.0132 (7)	0.0212 (7)	0.0042 (7)
C10	0.0425 (7)	0.0424 (7)	0.0417 (7)	0.0038 (6)	0.0117 (6)	0.0006 (6)

O—C4	1.4144 (15)	C4—H4	0.966 (13)
O—H	0.88 (2)	C5—C4	1.5128 (16)
N1—N2	1.3602 (16)	C5—C6	1.3869 (18)
N1—C2	1.3257 (18)	C5—C10	1.3866 (18)
N1—C3	1.4565 (16)	C6—C7	1.385 (2)
N2—C1	1.3178 (18)	C6—H6	0.982 (18)
N3—C2	1.322 (2)	C7—H7	1.01 (2)
C1—N3	1.341 (2)	C8—C7	1.378 (2)
C1—H1	0.96 (2)	C8—C9	1.376 (2)
C2—H2	0.961 (19)	C8—H8	0.989 (19)
C3—H31	1.012 (17)	C9—H9	0.974 (18)
C3—H32	0.977 (17)	C10—C9	1.3875 (19)
C4—C3	1.5194 (18)	C10—H10	0.959 (16)
C4—O—H	112.0 (14)	C3—C4—H4	108.0 (7)
C2—N1—N2	109.10 (12)	C5—C4—C3	109.94 (10)
C2—N1—C3	130.55 (13)	C5—C4—H4	109.7 (7)
N2—N1—C3	120.31 (11)	C6—C5—C4	119.78 (11)
C1—N2—N1	102.24 (12)	C10—C5—C4	121.28 (11)
C2—N3—C1	102.29 (13)	C10—C5—C6	118.92 (12)
N2—C1—N3	115.33 (15)	C5—C6—H6	119.2 (10)
N2—C1—H1	120.7 (11)	C7—C6—C5	120.68 (13)
N3—C1—H1	123.9 (11)	C7—C6—H6	120.1 (10)
N1—C2—H2	123.7 (11)	C6—C7—H7	119.0 (10)
N3—C2—N1	111.04 (15)	C8—C7—C6	120.00 (14)
N3—C2—H2	125.2 (11)	C8—C7—H7	121.0 (10)
N1—C3—C4	111.53 (10)	C7—C8—H8	120.9 (11)
N1—C3—H31	107.0 (9)	C9—C8—C7	119.79 (13)
N1—C3—H32	108.5 (9)	C9—C8—H8	119.3 (11)
C4—C3—H31	109.9 (9)	C8—C9—C10	120.47 (14)
C4—C3—H32	110.9 (9)	C8—C9—H9	120.6 (9)
H31—C3—H32	109.0 (13)	C10—C9—H9	118.9 (9)
O—C4—C3	109.53 (11)	C5—C10—C9	120.14 (13)
O—C4—C5	110.01 (10)	C5—C10—H10	119.5 (9)
O—C4—H4	109.6 (7)	C9—C10—H10	120.3 (9)
C2—N1—N2—C1	0.35 (16)	C6—C5—C4—C3	−92.44 (14)
C3—N1—N2—C1	178.19 (12)	C10—C5—C4—O	−34.88 (15)
N2—N1—C2—N3	−0.37 (19)	C10—C5—C4—C3	85.83 (14)
C3—N1—C2—N3	−177.91 (14)	C4—C5—C6—C7	178.13 (12)
C2—N1—C3—C4	94.22 (18)	C10—C5—C6—C7	−0.2 (2)
N2—N1—C3—C4	−83.09 (15)	C6—C5—C10—C9	0.30 (19)
N1—N2—C1—N3	−0.24 (19)	C4—C5—C10—C9	−177.99 (12)
C1—N3—C2—N1	0.2 (2)	C5—C6—C7—C8	−0.2 (2)
N2—C1—N3—C2	0.0 (2)	C9—C8—C7—C6	0.4 (2)
O—C4—C3—N1	−69.27 (14)	C7—C8—C9—C10	−0.3 (2)
C5—C4—C3—N1	169.73 (11)	C5—C10—C9—C8	−0.1 (2)
C6—C5—C4—O	146.85 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O—H···N2i	0.88 (2)	2.00 (2)	2.8645 (17)	166 (2)
C10—H10···Oii	0.959 (16)	2.566 (16)	3.3198 (17)	135.6 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H⋯N2i	0.88 (2)	2.00 (2)	2.8645 (17)	166 (2)
C10—H10⋯Oii	0.959 (16)	2.566 (16)	3.3198 (17)	135.6 (13)

Symmetry codes: (i) ; (ii) .