5-(2-Methoxy­benz­yl)-4-(2-methoxy­phen­yl)-4H-1,2,4-triazol-3-ol

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

doi:10.1107/S1600536809001482

. 2009 Jan 17;65(Pt 2):o329. doi: 10.1107/S1600536809001482

5-(2-Methoxybenzyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol

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

PMCID: PMC2968299 PMID: 21581933

Abstract

In the molecule of the title compound, C₁₇H₁₇N₃O₃, the triazole ring is oriented at dihedral angles of 88.09 (3) and 83.72 (3)° with respect to the 2-methoxybenzyl and 2-methoxyphenyl rings, respectively. The dihedral angle between the 2-methoxybenzyl and 2-methoxyphenyl rings is 52.95 (3)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. There is a π–π contact between the 2-methoxyphenyl rings [centroid–centroid distance = 3.811 (3) Å].

Related literature

For general background, see: Demirbas et al. (2002 ▶); Holla et al. (1998 ▶); Kritsanida et al. (2002 ▶); Omar et al. (1986 ▶); Paulvannan et al. (2000 ▶); Turan-Zitouni et al. (1999 ▶). For related structures, see: Öztürk et al. (2004a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₇N₃O₃
M _r = 311.34
Monoclinic,
a = 7.4941 (12) Å
b = 8.3730 (13) Å
c = 24.770 (4) Å
β = 97.455 (2)°
V = 1541.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
11912 measured reflections
3160 independent reflections
2888 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.091
S = 1.06
3160 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 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 I, global. DOI: 10.1107/S1600536809001482/hk2613sup1.cif

e-65-0o329-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001482/hk2613Isup2.hkl

e-65-0o329-Isup2.hkl^{(155.1KB, 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	0.890 (17)	1.911 (18)	2.7958 (14)	172.6 (15)

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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 activities including 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. 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 syntheses and biological activities of the aryloxyacetyl hydrazide derivatives and report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges, and they are comparable with those observed in related structures (Öztürk et al., 2004a,b). In the triazole ring, the N2=C1 [1.2960 (16) Å] bond has double bond character. Rings A (N1/N2/N3/C1/C2), B (C4-C9) and C (C11-C16) are, of course, planar and the dihedral angles between them are A/B = 88.09 (3)°, A/C = 83.72 (3)° and B/C = 52.95 (3)°.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. The π—π contact between the 2-methoxyphenyl rings, Cg1···Cg1ⁱ [symmetry code: (i) -x, 2 - y, -z, where Cg1 is the centroid of the ring C (C11-C16)] may further stabilize the structure, with centroid-centroid distance of 3.811 (3) Å.

Experimental

The synthesis of the title compound was carried out by refluxing a solution of 4-(2-methoxyphenyl)-1-(2-(2-methoxyphenyl)acetyl)semicarbazide (3.29 g, 10 mmol) in NaOH (2M) for 5 h. Crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield; 79%; m.p. 444–445 K).