2-(4H-1,2,4-Triazol-4-yl)phenol.

In the title compound, C(8)H(7)N(3)O, the dihedral angle between the benzene and triazole rings is 41.74 (12)°.

Related literature

For the use of substituted 1,2,4-triazoles as ligands, see: Ouellette et al. (2006 ▶); Zhang et al. (2005 ▶); Zhou et al. (2007 ▶, 2008 ▶). For related structures, see: Wiley & Hart (1953 ▶); Bartlett & Humphrey (1967 ▶); Li et al. (2004 ▶); Zhu et al. (2000 ▶); Xu et al. (2004 ▶).

Experimental

Crystal data

C8H7N3O

M = 161.17

Monoclinic,

a = 7.273 (3) Å

b = 14.265 (4) Å

c = 7.720 (3) Å

β = 90.93 (3)°

V = 800.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.42 × 0.37 × 0.35 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (Sphere in CrystalClear; Rigaku, 2002 ▶) T min = 0.815, T max = 1.000

5037 measured reflections

1460 independent reflections

863 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.237

S = 1.09

1460 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031739/jh2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031739/jh2195Isup2.hkl

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

C8H7N3O	F(000) = 336
Mr = 161.17	Dx = 1.337 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.273 (3) Å	Cell parameters from 1048 reflections
b = 14.265 (4) Å	θ = 2.6–27.4°
c = 7.720 (3) Å	µ = 0.09 mm−1
β = 90.93 (3)°	T = 293 K
V = 800.8 (5) Å3	Block, black
Z = 4	0.42 × 0.37 × 0.35 mm

Rigaku Mercury CCD diffractometer	1460 independent reflections
Radiation source: rotating-anode generator	863 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω scans	θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan (Sphere in CrystalClear; Rigaku, 2002)	h = −8→8
Tmin = 0.815, Tmax = 1.000	k = −16→17
5037 measured reflections	l = −9→8

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.237	w = 1/[σ2(Fo2) + (0.144P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1460 reflections	Δρmax = 0.44 e Å−3
110 parameters	Δρmin = −0.44 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.08 (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
C1	0.5881 (5)	0.7175 (2)	0.7593 (5)	0.0559 (10)
H1A	0.5053	0.7418	0.8381	0.067*
C2	0.7294 (5)	0.6248 (2)	0.5912 (4)	0.0510 (10)
H2A	0.7633	0.5718	0.5293	0.061*
C3	0.4535 (4)	0.5571 (2)	0.7425 (4)	0.0423 (8)
C4	0.5137 (4)	0.4665 (2)	0.7748 (4)	0.0448 (9)
C5	0.3858 (5)	0.4004 (2)	0.8286 (4)	0.0542 (10)
H5A	0.4233	0.3394	0.8527	0.065*
C6	0.2034 (5)	0.4252 (3)	0.8463 (5)	0.0651 (11)
H6A	0.1194	0.3807	0.8837	0.078*
C7	0.1443 (5)	0.5148 (3)	0.8091 (5)	0.0633 (11)
H7A	0.0210	0.5308	0.8200	0.076*
C8	0.2698 (5)	0.5804 (3)	0.7557 (5)	0.0582 (10)
H8A	0.2309	0.6408	0.7284	0.070*
N1	0.7219 (4)	0.76432 (19)	0.6942 (4)	0.0632 (10)
N2	0.8157 (4)	0.70426 (19)	0.5852 (4)	0.0618 (10)
N3	0.5836 (3)	0.62837 (17)	0.6985 (3)	0.0443 (8)
O1	0.6918 (3)	0.44556 (15)	0.7550 (3)	0.0582 (8)
H1B	0.7472	0.4923	0.7229	0.087*

	U11	U22	U33	U12	U13	U23
C1	0.068 (2)	0.0332 (18)	0.068 (2)	0.0041 (15)	0.0238 (18)	0.0022 (16)
C2	0.057 (2)	0.0414 (18)	0.0553 (19)	−0.0010 (15)	0.0129 (17)	0.0025 (15)
C3	0.0378 (18)	0.0426 (17)	0.0466 (17)	−0.0030 (14)	0.0046 (13)	0.0028 (14)
C4	0.0428 (19)	0.0414 (19)	0.0504 (17)	−0.0018 (14)	0.0042 (14)	0.0001 (14)
C5	0.060 (2)	0.0429 (19)	0.060 (2)	−0.0089 (15)	0.0074 (18)	0.0071 (16)
C6	0.058 (2)	0.075 (3)	0.063 (2)	−0.024 (2)	0.0154 (18)	−0.005 (2)
C7	0.047 (2)	0.070 (3)	0.072 (2)	−0.0036 (18)	0.0121 (18)	−0.001 (2)
C8	0.050 (2)	0.058 (2)	0.067 (2)	0.0034 (16)	0.0065 (17)	0.0065 (17)
N1	0.073 (2)	0.0368 (16)	0.081 (2)	−0.0025 (14)	0.0284 (17)	−0.0018 (15)
N2	0.065 (2)	0.0458 (17)	0.076 (2)	−0.0100 (14)	0.0222 (16)	−0.0004 (14)
N3	0.0449 (16)	0.0329 (15)	0.0553 (16)	0.0000 (11)	0.0117 (12)	0.0012 (11)
O1	0.0451 (15)	0.0400 (13)	0.0897 (19)	0.0004 (10)	0.0081 (12)	0.0087 (12)

C1—N1	1.289 (4)	C4—C5	1.393 (4)
C1—N3	1.356 (4)	C5—C6	1.382 (5)
C1—H1A	0.9300	C5—H5A	0.9300
C2—N2	1.297 (4)	C6—C7	1.378 (6)
C2—N3	1.357 (4)	C6—H6A	0.9300
C2—H2A	0.9300	C7—C8	1.375 (5)
C3—C8	1.382 (4)	C7—H7A	0.9300
C3—C4	1.385 (5)	C8—H8A	0.9300
C3—N3	1.433 (4)	N1—N2	1.388 (4)
C4—O1	1.340 (4)	O1—H1B	0.8200
N1—C1—N3	111.4 (3)	C7—C6—C5	120.9 (3)
N1—C1—H1A	124.3	C7—C6—H6A	119.5
N3—C1—H1A	124.3	C5—C6—H6A	119.5
N2—C2—N3	111.9 (3)	C8—C7—C6	119.2 (3)
N2—C2—H2A	124.1	C8—C7—H7A	120.4
N3—C2—H2A	124.1	C6—C7—H7A	120.4
C8—C3—C4	120.9 (3)	C7—C8—C3	120.4 (4)
C8—C3—N3	119.3 (3)	C7—C8—H8A	119.8
C4—C3—N3	119.8 (3)	C3—C8—H8A	119.8
O1—C4—C3	119.4 (3)	C1—N1—N2	107.4 (3)
O1—C4—C5	122.3 (3)	C2—N2—N1	105.9 (3)
C3—C4—C5	118.4 (3)	C1—N3—C2	103.4 (2)
C6—C5—C4	120.2 (3)	C1—N3—C3	126.6 (3)
C6—C5—H5A	119.9	C2—N3—C3	130.0 (3)
C4—C5—H5A	119.9	C4—O1—H1B	109.5