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

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

doi:10.1107/S1600536808023258

. 2008 Jul 26;64(Pt 8):o1604. doi: 10.1107/S1600536808023258

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

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

PMCID: PMC2962216 PMID: 21203297

Abstract

In the molecule of the title compound, C₁₀H₉N₃O, the triazole and phenyl rings are nearly perpendicular to each other, with a dihedral angle of 88.72 (4)°. In the crystal structure, intermolecular C—H⋯O and C—H⋯N hydrogen bonds link the molecules. There are C—H⋯π contacts between the 1,2,4-triazole rings, and between the phenyl and 1,2,4-triazole rings, and there is a weak π–π contact between the 1,2,4-triazole and phenyl rings [centroid-to-centroid distance = 4.547 (1) Å].

Related literature

For general background, see: Holla et al. (1996 ▶); Sengupta et al. (1978 ▶); Paulvannan et al. (2001 ▶); Sui et al. (1998 ▶); Bodey (1992 ▶). For related literature, see: Caira et al. (2004 ▶); Peeters et al. (1996 ▶); Özel Güven, Tahtacı et al. (2008 ▶); Özel Güven, Erdoğan et al. (2008 ▶). For synthesis, see: Liu et al. (2006 ▶).

Experimental

Crystal data

C₁₀H₉N₃O
M _r = 187.20
Orthorhombic,
a = 9.3129 (2) Å
b = 8.11660 (10) Å
c = 24.0475 (4) Å
V = 1817.73 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 (2) K
0.35 × 0.2 × 0.2 mm

Data collection

Bruker Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.968, T _max = 0.972
16799 measured reflections
2077 independent reflections
1736 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.145
S = 1.17
2077 reflections
164 parameters
All H-atom parameters refined
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023258/xu2439sup1.cif

e-64-o1604-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023258/xu2439Isup2.hkl

e-64-o1604-Isup2.hkl^{(58.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the rings N1–N3/C1/C2 and C5–C10, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Oⁱ	0.970 (16)	2.449 (15)	3.2595 (17)	140.9 (12)
C3—H32⋯Oⁱ	0.973 (16)	2.489 (16)	3.2601 (17)	136.1 (13)
C8—H8⋯N3ⁱⁱ	0.97 (2)	2.61 (2)	3.5405 (19)	160.2 (14)
C1—H1⋯Cg2ⁱⁱⁱ	1.001 (17)	2.840 (18)	3.620 (2)	135.20 (13)
C2—H2⋯Cg1^iv	0.972 (17)	3.013 (16)	3.829 (2)	142.42 (12)

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

Acknowledgments

The authors acknowledge the Zonguldak Karaelmas University Research Fund.

supplementary crystallographic information

Comment

In recent years, among antifungal agents, azole derivatives still have an important place in the class of systemic antifungal drugs. 1,2,4-Triazoles are biologically interesting molecules and their chemistry is receiving considerable attention, due to 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 a triazole ring such as fluconazole (Caira et al., 2004) and itraconazole (Peeters et al., 1996) 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). Recently, we reported the crystal structures of 1,2,4-triazole substituted alcohol (Özel Güven, Tahtacı et al., 2008) and benzimidazole substituted ketone (Özel Güven, Erdoğan et al., 2008). We report herein the crystal structure of the 1,2,4-triazole substituted ketone, (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, of course, planar and nearly perpendicular to each other with a dihedral angle of A/B = 88.72 (4)°. Atoms C3 and C4 are -0.028 (2) Å and -0.054 (1) Å away from the ring planes of A and B, respectively. The N1—C3—C4 [112.73 (11)°], C3—C4—C5 [116.93 (11)°], O—C4—C3 [120.73 (12)°] and O—C4—C5 [122.34 (12)°] bond angles are highly different from the corresponding values [111.53 (10)°, 109.94 (10)°, 109.53 (11)° and 110.01 (10)°, respectively] in 1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol, (II) (Özel Güven, Tahtacı et al., 2008). In ring A, the nearly equivalent N1—N2—C1 [101.81 (11)°] and C1—N3—C2 [102.23 (11)°] bond angles are narrowed, while highly different N3—C2—N1 [110.53 (13)°] and N3—C1—N2 [115.39 (12)°] bond angles are enlarged, as in (II).

In the crystal structure, intermolecular C—H···O and C—H···N hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure. The C—H···π contacts (Table 1) between the 1,2,4-triazole and the benzene rings and the 1,2,4-triazole rings and a π—π contact between the 1,2,4-triazole and benzene ring systems Cg2···Cg1ⁱ [symmetry code: (i) 1 - x, -y, -z, where Cg1 and Cg2 are centroids of the rings (N1–N3/C1/C2) and (C5–C10), respectively] further stabilize the structure, with centroid–centroid distance of 4.547 (1) Å.

Experimental

The title compound, (I), was synthesized by the reaction of 1H-1,2,4-triazole with 2-bromo-1-phenylethanone (Liu et al., 2006). To a vigorous stirred suspension of 1H-1,2,4-triazole (1105 mg, 16 mmol) and 2-bromo-1-phenylethanone (1990 mg, 10 mmol) in acetone (6 ml) was added triethylamine (2.2 ml) dropwise over a period of 1 h below 273 K, and the reaction mixture was stirred for another 30 min at room temperature. Then the mixture was filtered to remove triethylamine hydrobromide salt, the precipitate was washed with acetone, and the filtrate was evaporated under reduced pressure. The residue was dissolved in chloroform, and washed with water. After evaporation of chloroform, the yellow solid was obtained and crystallized from iso-propanol to obtain the title compound as colorless crystals (yield; 937 mg, 50%).