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

Abstract

In the title compound, C₈H₇N₃O, 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 _r = 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) ų

• 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

• Δρ_max = 0.44 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

supplementary crystallographic information

Comment

Many compounds with uncommon properties have been widely investigated by using substituted 1,2,4-triazoles ligands, resulting from their rich coordination fashions and broad potential applications in various fields (Ouellette et al. (2006); Zhang et al. (2005); Zhou et al. (2007); Zhou et al. (2008)). Substituted 1,2,4-triazoles can be synthesized from different amines and diformylhydrazine. The triazole ring, having strong -donor and weak-acceptor properties, potentially has two different coordination modes through three nitrogen-donor atoms coordinating to metal ions. Recently, we have prepared some new substituted 1,2,4-triazole derivatives and their transition-metal complexes, and we report here the crystal structure analysis of 2-(1H-1,2,4-Triazol-4-yl)phenol, (I).

Experimental

The title compound was prepared by reacting diformylhydrazine (0.6 mmol, 0.053 g) and o-aminophenol (0.6 mmol, 0.065 g) in a Telon-lined stainless steel autoclave in a furnace at 443 K for 2 d. The reaction vessel was then cooled to 293 K. The product was isolated and washed with hot water and hot ethanol and black crystals suitable for X-ray diffraction studies were obtained. The crystals are air-stable. Yield based on o-aminophenol: 0.062 g, 64%. Elemental analysis (%) for C8H7N3O, found (calculated): C 59.70 (59.61), H 4.25 (4.38), N 26.06 (26.08).

Refinement

Hydrogen atoms were allowed to ride on their respective parent atoms with C—H distances of 0.93 Å, and were included in the refinement with isotropic displacement parameters U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Fig. 2.

View of the 3-D structure of the title compound.

Crystal data

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

Data collection

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

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)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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