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

Muhammad Hanif; Ghulam Qadeer; Nasim Hasan Rama; Wai-Yeung Wong

doi:10.1107/S1600536808033990

. 2008 Oct 25;64(Pt 11):o2180. doi: 10.1107/S1600536808033990

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

Muhammad Hanif ^a, Ghulam Qadeer ^a, Nasim Hasan Rama ^a,^*, Wai-Yeung Wong ^b

PMCID: PMC2959665 PMID: 21581039

Abstract

In the molecule of the title compound, C₁₈H₁₉N₃O₃, the triazole ring is oriented with respect to the 3-methoxyphenyl and 2-methoxyphenyl rings at dihedral angles of 11.79 (3) and 89.22 (3)°, respectively. The dihedral angle between the two benzene rings is 85.95 (3)°. In the crystal structure, intermolecular O—H⋯N and C—H⋯O hydrogen bonds link the molecules. There is a π–π contact between the triazole and 3-methoxyphenyl rings [centroid–centroid distance = 3.916 (3) Å]. There is a π–π contact between the triazole and one of the 3-methoxyphenyl rings [centroid–centroid distance = 3.916 (3) Å ]. C—H⋯π contacts are also found between the benzene ring and the methyl groups of their 3-methoxy-substituents.

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

C₁₈H₁₉N₃O₃
M _r = 325.36
Monoclinic,
a = 10.5030 (11) Å
b = 14.1172 (14) Å
c = 11.3226 (11) Å
β = 98.192 (2)°
V = 1661.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.902, T _max = 1.000 (expected range = 0.884–0.980)
9949 measured reflections
4026 independent reflections
3212 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.146
S = 1.02
4026 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033990/hk2549sup1.cif

e-64-o2180-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033990/hk2549Isup2.hkl

e-64-o2180-Isup2.hkl^{(154.5KB, 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
O3—H3⋯N3ⁱ	0.82	1.94	2.7569 (15)	173
C5—H5A⋯O1ⁱⁱ	0.93	2.59	3.406 (2)	147
C8—H8A⋯O2	0.97	2.57	3.485 (2)	157
C4—H4A⋯Cg3ⁱⁱⁱ	0.93	3.25	4.004 (3)	140
C7—H7A⋯Cg3	0.93	3.16	4.067 (3)	165
C18—H18A⋯Cg2^iv	0.96	3.03	3.400 (3)	105
C18—H18B⋯Cg2^iv	0.96	3.08	3.400 (3)	101

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg2 and Cg3 are the centroids of the C2–C7 and C C12–C17 rings, respectively.

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 (Fig. 1) and crystal structure of the title compound.

In the molecule of the title compound (Fig. 2), 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, 2004b). In the triazole ring, the N3=C11 [1.3459 (17) Å] bond has double bond character. Rings A (C2-C7), B (N1/N2/N3/C10/C11) and C (C12-C17) are, of course, planar and the dihedral angles between them are A/B = 11.79 (3)°, A/C = 89.22 (3)° and B/C = 85.95 (3)°.

In the crystal structure, intramolecular C-H···O and intermolecular O-H···N and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 3), in which they may be effective in the stabilization of the structure. The π—π contact between the triazole and 3-methoxyphenyl rings, Cg1···Cg2ⁱ [symmetry code: (i) 1/2 + x, 1/2 - y, 1/2 + z, where Cg1 and Cg2 are the centroids of the rings B (N1/N2/N3/C10/C11) and A (C2-C7), respectively] may further stabilize the structure, with centroid-centroid distance of 3.916 (3) Å. There also exist C—H···π contacts (Table 1) between the phenyl rings and the methyl group and the 3-methoxyphenyl ring.

Experimental

The synthesis of the title compound (Fig. 1) was carried out by refluxing a solution of 4-(2-methoxyphenyl)-1-(3-(3-methoxyphenyl)propanoyl)semicarbazide (3.43 g, 10 mmol) in NaOH (2M) for 5 h. Single crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield; 71%, m.p. 454-455 K).