Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate

Yasemin Ünver; Yavuz Köysal; Hasan Tanak; Dilek Ünlüer; Şamil Işık

doi:10.1107/S160053681001603X

. 2010 May 8;66(Pt 6):o1294. doi: 10.1107/S160053681001603X

Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate

Yasemin Ünver ^a, Yavuz Köysal ^b,^*, Hasan Tanak ^c, Dilek Ünlüer ^a, Şamil Işık ^c

PMCID: PMC2979362 PMID: 21579391

Abstract

In the title compound, C₁₃H₁₅N₃O₃, the dihedral angle between the two aromatic ring is 51.06 (1)°. In the crystal, molecules are connected by pairs of N—H⋯O hydrogen bonds into centrosymmetric dimers.

Related literature

For the pharmacological activity of 1,2,4-triazole compounds, see: Chiu & Huskey (1998 ▶); Eliott et al. (1986 ▶, 1987 ▶); Griffin & Mannion (1986 ▶, 1987, 1987 ▶); Heubach et al. (1975 ▶, 1979 ▶); Husain & Amir (1986 ▶, 1987 ▶,); Tanaka (1974 ▶, 1975 ▶); Tsukuda et al. (1998 ▶); Witkoaski et al. (1972 ▶). For the biological activity of the triazole family, see: Unver et al. (2008 ▶, 2009 ▶). For a related structure, see: Tanak et al. (2010 ▶).

Experimental

Crystal data

C₁₃H₁₅N₃O₃
M _r = 261.28
Monoclinic,
a = 13.6111 (11) Å
b = 4.0970 (2) Å
c = 24.172 (2) Å
β = 100.063 (7)°
V = 1327.20 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.80 × 0.41 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer
8189 measured reflections
2581 independent reflections
1606 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.095
S = 0.93
2581 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001603X/bt5258sup1.cif

e-66-o1294-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001603X/bt5258Isup2.hkl

e-66-o1294-Isup2.hkl^{(124.2KB, 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
N1—H1⋯O1ⁱ	0.883 (19)	1.94 (2)	2.808 (2)	169.5 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer.

supplementary crystallographic information

Comment

1,2,4-triazole compounds posses important pharmacology activities such as antifungal and antiviral activities. Examples of such compounds bearing the 1,2,4- triazole residues are fluconazole (Tsukuda et al., 1998), the powerful azole antifungal agent as well as the potent antiviral N- nucleoside ribavirin (Witkoaski et al., 1972). Furthermore, various 1,2,4-triazole derivatives have been reported as fungicidal (Heubach et al., 1975, 1979), insecticidal (Tanaka, 1974, 1975), antimicrobial, (Griffin & Mannion, 1986, 1987) as well as anticonvulsants (Husain & Amir, 1986, 1987), antidepressants (Chiu & Huskey, 1998), and plant growth regulator anticoagulants (Eliott et al., 1986, 1987). Our laboratories reported the some biological activity of the triazole family (Unver et al., 2008; Unver et al., 2009). It is known that 1,2,4-triazol moieties interact strongly with heme iron, and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase. Furthermore, It was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatase inhibitors very useful for preventing breast cancer.

In the title compound, the plane of the -C(=O)—O- group is inclined at the angle of 4.23 (1)° with respect to the benzoate ring. The dihedral angle between the two aromatic ring is 51.06 (1)°. The 1,2,4-triazole ring is strictly planar and the maximum deviation of -0.0016 (2)Å for atom C1. The double bond distance in the triazol group is good agreement with our previous report,5-benzyl-4- (3,4-dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one (Tanak et al., 2010).

The molecules are connected by intermolecular N—H···O hydrogen bonds to centrosymmetric dimers. generating eight-membered ring, producing a R₂²(8) motif (Bernstein et al., 1995).

Experimental

Ethyl 2-(1-ethoxypropylidene)hydrazinecarboxylate (10 mmol) and ethyl 4-amino benzoate (10 mmol) was mixed without solvent and heated at 433-443°K for 2 h. The formed solid products were separated by filtration, purified by crystallization twice from ethanol, washed with Et₂O ether and dried in a vacuum. m p: 446°K.