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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1443.
Published online 2008 July 9. doi:  10.1107/S1600536808020771
PMCID: PMC2962074

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

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 [triangle]); Abdel-Rahman & Farghaly (2004 [triangle]); Chai et al. (2002 [triangle]); Jin et al. (2006 [triangle]); Mohd et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1443-scheme1.jpg

Experimental

Crystal data

  • C19H18Cl2N2O5
  • M r = 425.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1443-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.31 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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.

Refinement

All H atoms were included in the refinement at idealized positions and refined as riding, with C—H = 0.95 (aromatic), 0.98 (methyl), 1.00Å (methine) and Uiso(H) = xUeq(carrier atom), where x = 1.5 for methyl, 1.2 for all other H atoms.

Figures

Fig. 1.
A view of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.

Crystal data

C19H18Cl2N2O5F000 = 880
Mr = 425.25Dx = 1.465 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5138 reflections
a = 7.6743 (4) Åθ = 2.6–27.1º
b = 15.9516 (8) ŵ = 0.37 mm1
c = 15.7483 (8) ÅT = 173 (2) K
β = 90.8940 (10)ºBlock, colorless
V = 1927.63 (17) Å30.47 × 0.39 × 0.32 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer4159 independent reflections
Radiation source: fine-focus sealed tube3238 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 173(2) Kθmax = 27.2º
ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −8→9
Tmin = 0.845, Tmax = 0.891k = −20→18
10032 measured reflectionsl = −13→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.125  w = 1/[σ2(Fo2) + (0.0625P)2 + 1.3473P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4159 reflectionsΔρmax = 0.34 e Å3
257 parametersΔρmin = −0.31 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.29475 (7)0.36125 (4)0.89108 (4)0.04132 (18)
Cl20.44596 (8)0.54237 (4)0.85758 (4)0.03835 (17)
C10.7817 (3)0.05267 (12)0.99579 (13)0.0233 (4)
C20.7051 (3)−0.00409 (13)1.05104 (13)0.0243 (4)
H20.66670.01361.10530.029*
C30.6857 (3)−0.08687 (12)1.02552 (13)0.0254 (4)
C40.7416 (3)−0.11303 (12)0.94532 (13)0.0250 (4)
C50.8160 (3)−0.05492 (13)0.89080 (12)0.0239 (4)
C60.8351 (3)0.02847 (12)0.91572 (13)0.0245 (4)
H60.88420.06830.87820.029*
C70.8153 (3)0.13859 (12)1.02448 (13)0.0229 (4)
C80.9032 (3)0.27301 (12)1.00923 (13)0.0240 (4)
H81.02840.29031.00800.029*
C90.7883 (3)0.33955 (12)0.97007 (12)0.0231 (4)
C100.6145 (3)0.32243 (12)0.95089 (13)0.0248 (4)
H100.56760.26850.96190.030*
C110.5100 (3)0.38450 (13)0.91558 (13)0.0262 (4)
C120.5775 (3)0.46408 (12)0.90009 (13)0.0263 (4)
C130.7498 (3)0.48130 (13)0.91895 (14)0.0297 (5)
H130.79630.53540.90810.036*
C140.8548 (3)0.41901 (13)0.95392 (13)0.0268 (4)
H140.97350.43080.96700.032*
C150.9181 (3)0.29242 (13)1.16484 (14)0.0297 (5)
C160.8863 (4)0.25497 (16)1.25067 (15)0.0428 (6)
H16A0.99300.22771.27170.064*
H16B0.79250.21341.24610.064*
H16C0.85250.29931.29020.064*
C170.5778 (3)−0.12792 (16)1.16051 (15)0.0383 (6)
H17A0.6858−0.11001.18920.058*
H17B0.5312−0.17741.18930.058*
H17C0.4923−0.08241.16230.058*
C180.6289 (3)−0.22110 (15)0.85465 (16)0.0368 (5)
H18A0.5145−0.19410.85800.055*
H18B0.6143−0.28210.85440.055*
H18C0.6861−0.20360.80240.055*
C190.9654 (3)−0.03053 (15)0.76156 (14)0.0351 (5)
H19A0.89120.01690.74500.053*
H19B1.0019−0.06070.71060.053*
H19C1.0685−0.00980.79250.053*
N10.7969 (2)0.16636 (10)1.09988 (11)0.0248 (4)
N20.8524 (2)0.25043 (10)1.09633 (10)0.0251 (4)
O10.6131 (2)−0.14829 (9)1.07411 (10)0.0345 (4)
O20.7344 (2)−0.19688 (9)0.92680 (10)0.0354 (4)
O30.8701 (2)−0.08591 (9)0.81492 (9)0.0304 (3)
O40.87792 (19)0.19385 (8)0.96599 (9)0.0265 (3)
O50.9955 (2)0.35859 (10)1.15404 (11)0.0401 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0272 (3)0.0402 (3)0.0563 (4)−0.0036 (2)−0.0087 (2)0.0089 (3)
Cl20.0433 (3)0.0298 (3)0.0419 (3)0.0081 (2)−0.0035 (2)0.0093 (2)
C10.0220 (9)0.0187 (9)0.0290 (10)0.0012 (8)−0.0052 (8)0.0011 (8)
C20.0229 (10)0.0251 (10)0.0249 (10)0.0007 (8)−0.0009 (8)−0.0016 (8)
C30.0252 (10)0.0206 (10)0.0303 (11)−0.0032 (8)−0.0026 (8)0.0056 (8)
C40.0283 (10)0.0160 (9)0.0307 (11)0.0004 (8)−0.0043 (8)0.0000 (8)
C50.0243 (10)0.0225 (10)0.0247 (10)0.0030 (8)−0.0026 (8)−0.0024 (7)
C60.0255 (10)0.0217 (10)0.0261 (10)0.0000 (8)−0.0034 (8)0.0027 (8)
C70.0217 (9)0.0210 (10)0.0260 (10)0.0009 (8)−0.0011 (7)0.0024 (7)
C80.0276 (10)0.0172 (9)0.0273 (10)−0.0030 (8)0.0015 (8)−0.0023 (7)
C90.0280 (10)0.0194 (9)0.0219 (9)0.0003 (8)0.0017 (8)−0.0018 (7)
C100.0277 (10)0.0201 (10)0.0266 (10)−0.0032 (8)0.0012 (8)0.0004 (8)
C110.0243 (10)0.0283 (11)0.0261 (10)−0.0029 (8)0.0004 (8)0.0007 (8)
C120.0328 (11)0.0211 (10)0.0250 (10)0.0042 (8)0.0020 (8)0.0035 (8)
C130.0363 (12)0.0201 (10)0.0328 (11)−0.0040 (9)0.0030 (9)0.0025 (8)
C140.0257 (10)0.0216 (10)0.0332 (11)−0.0039 (8)0.0016 (8)−0.0016 (8)
C150.0363 (12)0.0215 (10)0.0312 (11)0.0032 (9)−0.0006 (9)−0.0070 (8)
C160.0668 (17)0.0339 (13)0.0277 (12)−0.0001 (12)−0.0001 (11)−0.0065 (10)
C170.0478 (14)0.0373 (13)0.0300 (12)−0.0120 (11)0.0034 (10)0.0064 (10)
C180.0350 (12)0.0305 (12)0.0448 (13)−0.0101 (10)−0.0005 (10)−0.0107 (10)
C190.0431 (13)0.0345 (12)0.0279 (11)−0.0098 (10)0.0052 (9)−0.0017 (9)
N10.0291 (9)0.0177 (8)0.0277 (9)−0.0016 (7)−0.0018 (7)−0.0001 (7)
N20.0309 (9)0.0199 (8)0.0245 (9)−0.0015 (7)0.0001 (7)−0.0013 (7)
O10.0480 (10)0.0232 (8)0.0325 (8)−0.0107 (7)0.0041 (7)0.0023 (6)
O20.0520 (10)0.0185 (7)0.0355 (9)−0.0018 (7)−0.0072 (7)−0.0029 (6)
O30.0388 (9)0.0246 (8)0.0278 (8)−0.0043 (6)0.0048 (6)−0.0035 (6)
O40.0367 (8)0.0168 (7)0.0262 (7)−0.0013 (6)0.0029 (6)−0.0010 (5)
O50.0531 (10)0.0255 (8)0.0416 (10)−0.0062 (7)−0.0027 (8)−0.0096 (7)

Geometric parameters (Å, °)

Cl1—C111.730 (2)C11—C121.394 (3)
Cl2—C121.734 (2)C12—C131.378 (3)
C1—C61.387 (3)C13—C141.388 (3)
C1—C21.392 (3)C13—H130.9500
C1—C71.465 (3)C14—H140.9500
C2—C31.388 (3)C15—O51.224 (3)
C2—H20.9500C15—N21.360 (3)
C3—O11.367 (2)C15—C161.501 (3)
C3—C41.404 (3)C16—H16A0.9800
C4—O21.370 (2)C16—H16B0.9800
C4—C51.392 (3)C16—H16C0.9800
C5—O31.364 (2)C17—O11.429 (3)
C5—C61.394 (3)C17—H17A0.9800
C6—H60.9500C17—H17B0.9800
C7—N11.277 (3)C17—H17C0.9800
C7—O41.368 (2)C18—O21.438 (3)
C8—O41.446 (2)C18—H18A0.9800
C8—N21.476 (3)C18—H18B0.9800
C8—C91.506 (3)C18—H18C0.9800
C8—H81.0000C19—O31.429 (3)
C9—C101.390 (3)C19—H19A0.9800
C9—C141.391 (3)C19—H19B0.9800
C10—C111.385 (3)C19—H19C0.9800
C10—H100.9500N1—N21.409 (2)
C6—C1—C2121.40 (18)C12—C13—H13120.3
C6—C1—C7119.20 (18)C14—C13—H13120.3
C2—C1—C7119.32 (18)C13—C14—C9120.8 (2)
C3—C2—C1118.83 (19)C13—C14—H14119.6
C3—C2—H2120.6C9—C14—H14119.6
C1—C2—H2120.6O5—C15—N2119.3 (2)
O1—C3—C2124.24 (19)O5—C15—C16123.7 (2)
O1—C3—C4115.06 (18)N2—C15—C16117.0 (2)
C2—C3—C4120.70 (18)C15—C16—H16A109.5
O2—C4—C5122.30 (19)C15—C16—H16B109.5
O2—C4—C3118.03 (18)H16A—C16—H16B109.5
C5—C4—C3119.42 (18)C15—C16—H16C109.5
O3—C5—C4115.61 (18)H16A—C16—H16C109.5
O3—C5—C6124.10 (19)H16B—C16—H16C109.5
C4—C5—C6120.27 (19)O1—C17—H17A109.5
C1—C6—C5119.37 (19)O1—C17—H17B109.5
C1—C6—H6120.3H17A—C17—H17B109.5
C5—C6—H6120.3O1—C17—H17C109.5
N1—C7—O4116.60 (17)H17A—C17—H17C109.5
N1—C7—C1126.14 (18)H17B—C17—H17C109.5
O4—C7—C1117.22 (17)O2—C18—H18A109.5
O4—C8—N2100.90 (14)O2—C18—H18B109.5
O4—C8—C9110.42 (16)H18A—C18—H18B109.5
N2—C8—C9113.01 (16)O2—C18—H18C109.5
O4—C8—H8110.7H18A—C18—H18C109.5
N2—C8—H8110.7H18B—C18—H18C109.5
C9—C8—H8110.7O3—C19—H19A109.5
C10—C9—C14119.51 (18)O3—C19—H19B109.5
C10—C9—C8120.30 (18)H19A—C19—H19B109.5
C14—C9—C8120.18 (18)O3—C19—H19C109.5
C11—C10—C9119.63 (19)H19A—C19—H19C109.5
C11—C10—H10120.2H19B—C19—H19C109.5
C9—C10—H10120.2C7—N1—N2104.79 (16)
C10—C11—C12120.43 (19)C15—N2—N1123.09 (17)
C10—C11—Cl1118.75 (16)C15—N2—C8121.12 (17)
C12—C11—Cl1120.82 (16)N1—N2—C8110.70 (15)
C13—C12—C11120.13 (19)C3—O1—C17117.06 (17)
C13—C12—Cl2119.37 (16)C4—O2—C18116.81 (17)
C11—C12—Cl2120.49 (17)C5—O3—C19117.18 (16)
C12—C13—C14119.45 (19)C7—O4—C8106.95 (15)
C6—C1—C2—C31.4 (3)C10—C11—C12—Cl2−178.89 (16)
C7—C1—C2—C3−175.26 (18)Cl1—C11—C12—Cl21.2 (3)
C1—C2—C3—O1179.76 (19)C11—C12—C13—C14−0.4 (3)
C1—C2—C3—C4−0.2 (3)Cl2—C12—C13—C14179.24 (16)
O1—C3—C4—O2−6.1 (3)C12—C13—C14—C90.0 (3)
C2—C3—C4—O2173.88 (18)C10—C9—C14—C130.0 (3)
O1—C3—C4—C5179.51 (18)C8—C9—C14—C13−179.09 (19)
C2—C3—C4—C5−0.5 (3)O4—C7—N1—N2−0.3 (2)
O2—C4—C5—O34.6 (3)C1—C7—N1—N2177.36 (18)
C3—C4—C5—O3178.68 (18)O5—C15—N2—N1165.36 (19)
O2—C4—C5—C6−174.01 (18)C16—C15—N2—N1−16.2 (3)
C3—C4—C5—C60.1 (3)O5—C15—N2—C812.9 (3)
C2—C1—C6—C5−1.8 (3)C16—C15—N2—C8−168.66 (19)
C7—C1—C6—C5174.89 (18)C7—N1—N2—C15−153.3 (2)
O3—C5—C6—C1−177.46 (18)C7—N1—N2—C81.6 (2)
C4—C5—C6—C11.0 (3)O4—C8—N2—C15153.32 (18)
C6—C1—C7—N1−169.31 (19)C9—C8—N2—C15−88.8 (2)
C2—C1—C7—N17.4 (3)O4—C8—N2—N1−2.2 (2)
C6—C1—C7—O48.3 (3)C9—C8—N2—N1115.70 (18)
C2—C1—C7—O4−174.95 (17)C2—C3—O1—C17−9.0 (3)
O4—C8—C9—C1045.1 (2)C4—C3—O1—C17171.03 (19)
N2—C8—C9—C10−67.1 (2)C5—C4—O2—C18−65.1 (3)
O4—C8—C9—C14−135.80 (19)C3—C4—O2—C18120.8 (2)
N2—C8—C9—C14112.0 (2)C4—C5—O3—C19−172.83 (18)
C14—C9—C10—C110.3 (3)C6—C5—O3—C195.7 (3)
C8—C9—C10—C11179.43 (18)N1—C7—O4—C8−1.2 (2)
C9—C10—C11—C12−0.7 (3)C1—C7—O4—C8−179.02 (17)
C9—C10—C11—Cl1179.22 (15)N2—C8—O4—C71.92 (19)
C10—C11—C12—C130.7 (3)C9—C8—O4—C7−117.85 (17)
Cl1—C11—C12—C13−179.17 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O40.952.432.772 (2)101
C8—H8···O2i1.002.563.184 (3)121
C10—H10···O1ii0.952.433.302 (3)153
C13—H13···O5iii0.952.533.426 (3)156
C16—H16B···N10.982.422.839 (3)105
C18—H18A···N1ii0.982.533.468 (3)160
C18—H18C···O30.982.362.916 (3)116
C19—H19A···O5iv0.982.583.233 (3)124

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+2, −y+1, −z+2; (iv) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2269).

References

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