4-(4-Methoxy­phen­yl)-3-[2-(2-methoxy­phen­yl)eth­yl]-1H-1,2,4-triazol-5(4H)-one

Muhammad Hanif; Ghulam Qadeer; Nasim Hasan Rama; Javeed Akhtar; Madeleine Helliwell

doi:10.1107/S1600536809002815

. 2009 Jan 31;65(Pt 2):o429. doi: 10.1107/S1600536809002815

4-(4-Methoxyphenyl)-3-[2-(2-methoxyphenyl)ethyl]-1H-1,2,4-triazol-5(4H)-one

Muhammad Hanif ^a, Ghulam Qadeer ^a,^*, Nasim Hasan Rama ^a, Javeed Akhtar ^b, Madeleine Helliwell ^b

PMCID: PMC2968336 PMID: 21582015

Abstract

The title compound, C₁₈H₁₉N₃O₃, is a biologically active triazole derivative. The five-membered ring is oriented with respect to the six-membered rings at dihedral angles of 51.59 (4) and 61.37 (4)°. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen-bond interactions between centrosymmetrically related molecules [the dihedral angle between the benzene rings is 47.44 (5)°].

Related literature

For the biological activities of triazole derivatives, see: Demirbas et al. (2002 ▶); Holla et al. (1998 ▶); Omar et al. (1986 ▶); Paulvannan et al. (2000 ▶); Turan-Zitouni et al. (1999 ▶); Kritsanida et al. (2002 ▶). For related structures, see: Öztürk et al. (2004a ▶,b ▶). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₈H₁₉N₃O₃
M _r = 325.36
Monoclinic,
a = 12.5396 (19) Å
b = 9.1840 (14) Å
c = 14.041 (2) Å
β = 96.613 (3)°
V = 1606.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.50 × 0.50 × 0.50 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8654 measured reflections
3278 independent reflections
2631 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.083
S = 1.01
3278 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002815/rz2290sup1.cif

e-65-0o429-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002815/rz2290Isup2.hkl

e-65-0o429-Isup2.hkl^{(160.8KB, 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
N3—H3N⋯O1ⁱ	0.913 (13)	1.870 (13)	2.7787 (12)	172.7 (12)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

Substituted triazole derivatives display significant biological activity including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). The biological activity is closely related to the structure, possibly being due to the presence of the —N—C═S unit (Omar et al., 1986). We are interested in the synthesis and biological activity of aryloxyacetyl hydrazide derivatives and report here the synthesis and crystal structure of the title compound (Fig. 1).

In the crystal structure of the title molecule, the bond lengths and angles are within normal range and comparable with those observed in related structures (Öztürk et al., 2004a,b). In the triazole ring, the N3═C11 (1.2970 (14) Å) bond shows double bond character. The rings A (N1—N3/ C1/ C2), B (C5—C10) and C (C12—C17) are planar and the dihedral angles between them are A/B = 78.11 (3)°, A/C = 56.04 (3)° and B/C = 33.23 (3)°. In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1) generating a ring of graph-set R²₂(8) (Etter, 1990; Bernstein et al., 1995).

Experimental

The synthesis of the title compound was carried out by refluxing a solution of 4-(4-methoxyphenyl)-1-(3-(2-methoxyphenyl)propanoyl)semicarbazide (3.43 g, 10 mmol) in 2M NaOH for 5 h. Single crystals suitable for X-ray measurements were obtained on slow evaporation of an aqeous ethanol solution at room temperature (yield: 84%; m.p. 431–432 K).