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

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

doi:10.1107/S1600536809002840

. 2009 Jan 28;65(Pt 2):o387. doi: 10.1107/S1600536809002840

4-(3-Methoxyphenyl)-3-[2-(4-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: PMC2968207 PMID: 21581982

Abstract

The asymmetric unit of the title compound, C₁₈H₁₉N₃O₃, contains two crystallographically independent but similar molecules. The triazole ring is oriented with respect to the benzene rings to form dihedral angles of 57.96 (6) and 7.01 (6)° in one molecule, and 64.37 (5) and 10.73 (5)° in the other. The two independent molecules are linked into a dimer by intermolecular N—H⋯O hydrogen bonds.

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 = 26.784 (4) Å
b = 14.824 (2) Å
c = 8.1108 (11) Å
β = 96.522 (3)°
V = 3199.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.50 × 0.50 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
18196 measured reflections
6524 independent reflections
4463 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.083
S = 0.93
6524 reflections
445 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 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 I, global. DOI: 10.1107/S1600536809002840/rz2291sup1.cif

e-65-0o387-sup1.cif^{(29.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002840/rz2291Isup2.hkl

e-65-0o387-Isup2.hkl^{(319.3KB, 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⋯O4ⁱ	0.972 (18)	1.784 (19)	2.7463 (18)	169.6 (17)
N6—H6N⋯O1ⁱⁱ	0.931 (16)	1.936 (17)	2.8429 (18)	164.2 (16)

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

Acknowledgments

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

supplementary crystallographic information

Comment

Substituted triazole derivatives are an important class of organic compounds showing significant biological activity, such as antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral (Kritsanida et al., 2002) activities. As a continuation of our interest in the synthesis and biological activity of aryloxyacetyl hydrazide derivatives, we report here the synthesis and crystal structure of the title compound (Fig. 1).

The asymmetric unit of the title compound consists of two crystallographically independent molecules with very similar geometry. All bond lengths and angles are unexceptional and comparable with those observed in related structures (Öztürk et al., 2004a,b). The N2═C1 (1.2955 (19) Å) and N5═C19 (1.2971 (19) Å) bonds show double bond character. The dihedral angles formed by the triazole ring with the aromatic rings of the 4-methoxyphenyl and 3-methoxyphenyl groups are 57.96 (6) and 7.01 (6)° in the molecule containing the N1–N3 atoms, and 64.37 (6) and 10.73 (5)° in the molecule containing the N4–N6 atoms. In the crystal packing (Fig. 2), the two independent molecules are linked into a dimer 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-(3-methoxyphenyl)-1-(3-(4-methoxyphenyl)propanoyl)semicarbazide (3.43 g, 10 mmol) in 2 M 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: 90%; m.p. 407–408 K).