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

Özden Özel Güven; Hakan Tahtacı; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536808017303

. 2008 Jun 13;64(Pt 7):o1254. doi: 10.1107/S1600536808017303

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

Özden Özel Güven ^a, Hakan Tahtacı ^a, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC2961775 PMID: 21202888

Abstract

In the title compound, C₁₀H₁₁N₃O, the planar five- and six-membered rings are nearly parallel to each other, making a dihedral angle of 2.52 (5)°. Weak intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers and strong intermolecular 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 _r = 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
Δρ_max = 0.16 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-64-o1254-sup1.cif^{(15.9KB, cif)}

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

e-64-o1254-Isup2.hkl^{(60.4KB, hkl)}

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

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)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge Zonguldak Karaelmas University Research Fund for support.

supplementary crystallographic information

Comment

Azole derivatives continue to occupy an important place among systemic antifungal drugs. 1,2,4-triazoles are biologically interesting and their chemistry is receiving considerable attention due to their antihypertensive, antifungal and antibacterial properties (Holla et al., 1996; Sengupta et al., 1978; Paulvannan et al., 2001; Sui et al., 1998). The azole antifungals possessing an imidazole or triazole ring (such as miconazole, ketoconazole, fluconazole, econazole and itraconazole) inhibit the synthesis of sterols in fungi by inhibiting cytochrome P-450-dependent 14α-lanosterol demethylase (P-450_14DM) and prevent cytochrome P-450 activity (Bodey, 1992). The crystal structures of miconazole (Peeters et al., 1997a), ketoconazole (Peeters et al., 1979b), fluconazole (Caira et al., 2004), econazole (Freer et al., 1986) and itraconazole (Peeters et al., 1996) have already been reported. This paper describes the crystal structure of a 1,2,4-triazole derivative, (I).

In (I) the bond lengths and angles are generally within normal ranges (Fig. 1). The 1,2,4-triazole and benzene rings, A (N1—N3/C1/C2) and B (C5—C10), are planar and nearly parallel to each other with a dihedral angle of A/B = 2.52 (5)°. Atoms C3 and C4 are 0.040 (1) Å and -0.046 (1) Å away from the ring planes of A and B, respectively indicating that they are coplanar with the adjacent rings. The N1—C3—C4 [111.53 (10)°] and C3—C4—C5 [109.94 (10)°] bond angles are a little different from each other, while O—C4—C3 [109.53 (11)°] and O—C4—C5 [110.01 (10)°] bond angles are nearly equal. In ring A, the equivalent N1—N2—C1 [102.24 (12)°] and C1—N3—C2 [102.29 (13)°] bond angles are narrowed and approximately equal to one another, while the N3—C2—N1 [111.04 (15)°] and N3—C1—N2 [115.33 (15)°] bond angles are quite different and larger than normal, probably due to the strong intermolecular O—H···N hydrogen bonds (Table 1).

In the crystal packing weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers and strong intermolecular O—H···N hydrogen bonds (Table 1) link the dimers along the b axis (Fig. 2).

Experimental

For the preparation of the title compound, a mixture of 1-phenyl-2-(1H-1,2,4 -triazol-1-yl)ethanone (800 mg, 4.27 mmol) and sodiumborohydride (324 mg, 8.54 mmol) in ethanol (13 ml) was refluxed for 5 h. After evaporation of solvent, the mixture was neutralized with dilute HCl and then refluxed for 30 min. After the mixture was cooled, the solution was alkalinized with NaOH and the precipitate was collected and crystallized from benzene to obtain colorless crystals (yield; 577 mg, 71%).