1-[2-(3,4-Dichloro­phen­yl)-5-(3,4,5-trimethoxy­phen­yl)-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone

Dao-Hang He; Yong-Chuang Zhu

doi:10.1107/S1600536808020771

. 2008 Jul 9;64(Pt 8):o1443. doi: 10.1107/S1600536808020771

1-[2-(3,4-Dichlorophenyl)-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone

Dao-Hang He ^a,^*, Yong-Chuang Zhu ^a

PMCID: PMC2962074 PMID: 21203158

Abstract

The title compound, C₁₉H₁₈Cl₂N₂O₅, was synthesized by the reaction of N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide and acetic anhydride. The oxadiazole ring makes dihedral angles of 82.82 (7) and 9.92 (7)° with the 3,4-dichlorobenzene and the 3,4,5-trimethoxybenzene ring planes, respectively. The crystal structure is stabilized by intermolecular C—H⋯ O and C—H⋯ N hydrogen bonds. Intramolecular C—H⋯O and C—H⋯N hydrogen bonds are also present.

Related literature

For related literature, see: Abdel et al. (2003 ▶); Abdel-Rahman & Farghaly (2004 ▶); Chai et al. (2002 ▶); Jin et al. (2006 ▶); Mohd et al. (2004 ▶).

Experimental

Crystal data

C₁₉H₁₈Cl₂N₂O₅
M _r = 425.25
Monoclinic,
a = 7.6743 (4) Å
b = 15.9516 (8) Å
c = 15.7483 (8) Å
β = 90.8940 (10)°
V = 1927.63 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 173 (2) K
0.47 × 0.39 × 0.32 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.845, T _max = 0.890
10032 measured reflections
4159 independent reflections
3238 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.125
S = 1.04
4159 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020771/wn2269sup1.cif

e-64-o1443-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020771/wn2269Isup2.hkl

e-64-o1443-Isup2.hkl^{(203.8KB, 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
C6—H6⋯O4	0.95	2.43	2.772 (2)	101
C8—H8⋯O2ⁱ	1.00	2.56	3.184 (3)	121
C10—H10⋯O1ⁱⁱ	0.95	2.43	3.302 (3)	153
C13—H13⋯O5ⁱⁱⁱ	0.95	2.53	3.426 (3)	156
C16—H16B⋯N1	0.98	2.42	2.839 (3)	105
C18—H18A⋯N1ⁱⁱ	0.98	2.53	3.468 (3)	160
C18—H18C⋯O3	0.98	2.36	2.916 (3)	116
C19—H19A⋯O5^iv	0.98	2.58	3.233 (3)	124

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

Acknowledgments

The authors thank Guangdong Provincial Natural Science Foundation of China (No. 04300531) for financial assistance.

supplementary crystallographic information

Comment

1,3,4-Oxadiazole derivatives are well known to possess a diverse range of bioactivities in the pharmaceutical and agrochemical fields; these include insecticidal, antibacterial, anticancer, and anti-inflammatory activities (Abdel et al., 2003; Abdel-Rahman & Farghaly, 2004; Chai et al., 2002; Mohd et al., 2004). Here we report the synthesis and crystal structure of a 1,3,4-oxadiazole derivative containing the 3,4,5-trimethoxyphenyl unit (Fig. 1).

The bond lengths and angles in the title compound are in good agreement with expected values. Though the C8 carbon of the oxadiazole ring is sp³ hybridized, the oxadiazole ring is essentially planar. The oxadiazole ring makes dihedral angles of 82.82 (7)° and 9.92 (7)° with the 3,4-dichlorobenzene and the 3,4,5-trimethoxybenzene ring planes, respectively. These angles are somewhat different from those in a similar crystal structure (Jin et al., 2006). The crystal structure exhibits intermolecular C—H··· O and C—H···N hydrogen bonds which stabilize the molecule. Intramolecular C—H···O and C—H···N hydrogen bonds are also present.

Experimental

N'-(3,4-Dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide (0.38 g, 1 mmol) in acetic anhydride (8 ml) was refluxed for 2 h until the starting material disappeared, as evidenced by TLC. The resulting cool mixture was then poured into cold water, after filtration. The residue was recrystallized by slow evaporation of a methanol solution.