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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1196–o1197.
Published online 2010 April 28. doi:  10.1107/S1600536810011153
PMCID: PMC2979016

5-(2,4-Dichloro­phen­yl)-3-(4-nitro­phen­yl)-1,2,4-oxadiazole

Abstract

In the title compound, C14H7Cl2N3O3, the dichloro­phenyl and nitro­phenyl rings form dihedral angles of 5.4 (2) and 4.0 (2)°, respectively, with the oxadiazole ring. The nitro group is twisted out of the attached benzene ring by a dihedral angle of 10.4 (3)°. In the crystal, mol­ecules are linked into a chain along the a axis by C—H(...)N hydrogen bonds.

Related literature

For the biological activity of heterocyclic compounds including oxadiazo­les, see: Andersen et al. (1994 [triangle]); Showell et al. (1991 [triangle]); Watjen et al. (1989 [triangle]); Swain et al. (1991 [triangle]); Clitherow et al. (1996 [triangle]); Isloor et al. (2010 [triangle]); Chandrakantha et al. (2010 [triangle]). For related structures, see: Wang et al. (2006 [triangle]); Fun et al. (2010a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1196-scheme1.jpg

Experimental

Crystal data

  • C14H7Cl2N3O3
  • M r = 336.13
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1196-efi1.jpg
  • a = 13.5272 (5) Å
  • b = 6.5362 (2) Å
  • c = 15.6880 (5) Å
  • V = 1387.08 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.48 mm−1
  • T = 296 K
  • 0.37 × 0.11 × 0.04 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.843, T max = 0.980
  • 9845 measured reflections
  • 2658 independent reflections
  • 2029 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.091
  • S = 1.06
  • 2658 reflections
  • 199 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.22 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1243 Friedel pairs
  • Flack parameter: −0.01 (7)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; 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 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011153/ci5063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011153/ci5063Isup2.hkl

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

Acknowledgments

AMI is grateful to Professor Sandeep Sancheti, Director, National Institute of Technology-Karnataka, India, for providing research facilities and encouragement. HKF and MMR thank Universiti Sains Malaysia for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012).

supplementary crystallographic information

Comment

Heterocyclic compounds are becoming increasingly important in recent years due to their pharmacological activities (Isloor et al., 2010). Nitrogen- and oxygen-containing five/six-membered heterocyclic compounds are of enormous significance in the field of medicinal chemistry (Chandrakantha et al., 2010). Oxadiazoles play a very vital role in the preparation of various biologically active drugs with anti-inflammatory (Andersen et al., 1994), anti-cancer (Showell et al., 1991), anti-HIV (Watjen et al., 1989), anti-diabetic and anti-microbial (Swain et al., 1991) activities. The results of biological studies showed that oxadiazole derivatives also possess maximum anti-inflammatory, analgesic and minimum ulcerogenic and lipid per-oxidation (Clitherow et al., 1996) properties.

Bond lengths and angles in the title molecule (Fig.1) are within the normal range and comparable to those observed in related structures (Wang et al., 2006; Fun et al., 2010a,b). The oxadiazole ring (C7/C8/N1/N2/O1) forms dihedral angles of 5.4 (2)° and 4.0 (2)°, respectively, with with the C1–C6 and C9–C14 benzene rings. The plane of the nitro group is twisted out of the C9–C14 benzene ring by a dihedral of 10.4 (3)°.

In the crystal structure (Fig. 2), the molecules are connected by intermolecular C13—H13A···N1 hydrogen bonds (Table 1) forming chains along the a axis.

Experimental

The title compound was prepared by heating a solution of 2,4-dichlorobenzoyl chloride (1.15 g, 0.02 mol) and N'-hydroxy-4-nitrobenzamidine (1 g, 0.02 mol) in pyridine (30 ml). The reaction mixture was heated at 114°C for 1.5 h and concentrated under vacuum. Further purification was done by column chromatography. The solid obtained was recrystallized using dichloromethane (yield: 1.0 g (55%), m.p 458-461 K).

Refinement

H atoms were positioned geometrically with C-H = 0.93 Å and were refined using a riding model with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) chains along the a axis. H atoms not involved in the interactions have been omitted.

Crystal data

C14H7Cl2N3O3F(000) = 680
Mr = 336.13Dx = 1.610 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2389 reflections
a = 13.5272 (5) Åθ = 2.6–30.1°
b = 6.5362 (2) ŵ = 0.48 mm1
c = 15.6880 (5) ÅT = 296 K
V = 1387.08 (8) Å3Plate, colourless
Z = 40.37 × 0.11 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer2658 independent reflections
Radiation source: fine-focus sealed tube2029 reflections with I > 2σ(I)
graphiteRint = 0.045
[var phi] and ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −13→16
Tmin = 0.843, Tmax = 0.980k = −7→8
9845 measured reflectionsl = −17→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.091w = 1/[σ2(Fo2) + (0.0361P)2 + 0.1623P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2658 reflectionsΔρmax = 0.24 e Å3
199 parametersΔρmin = −0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 1243 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.37074 (7)1.17134 (15)0.20371 (7)0.0672 (3)
Cl20.08039 (7)0.73697 (16)0.34239 (10)0.0814 (4)
O10.15793 (17)0.3687 (4)0.41360 (18)0.0643 (8)
O20.3673 (2)−0.6615 (5)0.6679 (2)0.0975 (12)
O30.5067 (2)−0.5915 (5)0.6109 (2)0.0959 (11)
N10.1636 (2)0.1879 (5)0.4615 (2)0.0653 (10)
N20.3154 (2)0.2966 (4)0.4278 (2)0.0454 (7)
N30.4200 (3)−0.5541 (5)0.6249 (2)0.0646 (9)
C10.3731 (2)0.6429 (5)0.3289 (2)0.0515 (10)
H1A0.41980.54720.34630.062*
C20.4043 (3)0.8143 (5)0.2848 (3)0.0562 (10)
H2A0.47090.83460.27290.067*
C30.3342 (3)0.9546 (5)0.2589 (2)0.0478 (9)
C40.2351 (3)0.9269 (5)0.2767 (2)0.0493 (9)
H4A0.18881.02330.25940.059*
C50.2060 (2)0.7551 (5)0.3204 (2)0.0484 (9)
C60.2735 (2)0.6087 (4)0.3481 (2)0.0417 (8)
C70.2522 (2)0.4235 (5)0.3964 (2)0.0423 (8)
C80.2581 (3)0.1536 (5)0.4676 (2)0.0434 (8)
C90.2984 (2)−0.0278 (5)0.5105 (2)0.0411 (8)
C100.2372 (2)−0.1701 (5)0.5499 (2)0.0463 (9)
H10A0.1692−0.14930.55010.056*
C110.2759 (3)−0.3416 (5)0.5887 (2)0.0491 (10)
H11A0.2350−0.43570.61580.059*
C120.3767 (3)−0.3693 (5)0.5861 (2)0.0457 (9)
C130.4388 (3)−0.2323 (5)0.5472 (2)0.0547 (10)
H13A0.5066−0.25590.54580.066*
C140.3995 (2)−0.0590 (5)0.5103 (2)0.0508 (9)
H14A0.44110.03690.48510.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0778 (7)0.0595 (6)0.0642 (6)−0.0179 (5)0.0002 (6)0.0100 (6)
Cl20.0403 (4)0.0675 (6)0.1363 (11)−0.0026 (5)−0.0083 (7)0.0236 (7)
O10.0468 (14)0.0596 (15)0.086 (2)0.0041 (12)0.0112 (14)0.0228 (15)
O20.089 (2)0.0758 (19)0.127 (3)0.0000 (18)0.006 (2)0.045 (2)
O30.070 (2)0.094 (2)0.124 (3)0.0193 (18)−0.001 (2)0.035 (2)
N10.0445 (17)0.0621 (19)0.089 (3)0.0045 (15)0.0144 (19)0.0230 (19)
N20.0442 (16)0.0428 (15)0.0493 (18)−0.0004 (14)0.0019 (15)−0.0026 (15)
N30.066 (2)0.061 (2)0.066 (2)0.0007 (19)−0.007 (2)0.0065 (19)
C10.046 (2)0.0437 (19)0.065 (3)0.0046 (14)0.0124 (19)−0.0034 (18)
C20.051 (2)0.054 (2)0.065 (3)−0.0046 (18)0.015 (2)−0.009 (2)
C30.061 (2)0.044 (2)0.038 (2)−0.0077 (17)0.0005 (18)−0.0042 (17)
C40.050 (2)0.0450 (19)0.053 (2)0.0004 (16)−0.0104 (18)0.0052 (18)
C50.0418 (18)0.0520 (19)0.052 (2)−0.0054 (16)−0.0026 (17)−0.0072 (19)
C60.0440 (18)0.0357 (15)0.046 (2)0.0000 (13)0.0014 (17)−0.0082 (18)
C70.0402 (18)0.0428 (17)0.044 (2)−0.0013 (16)0.0029 (17)−0.0085 (17)
C80.0472 (19)0.0424 (17)0.040 (2)−0.0011 (17)0.0037 (19)−0.0072 (16)
C90.0462 (19)0.0400 (17)0.0370 (19)0.0007 (15)0.0012 (17)−0.0081 (16)
C100.0367 (18)0.052 (2)0.050 (2)0.0023 (16)0.0099 (17)−0.0048 (18)
C110.054 (2)0.0464 (19)0.047 (2)−0.0071 (16)0.0106 (19)0.0000 (18)
C120.050 (2)0.0432 (19)0.043 (2)−0.0008 (16)−0.0008 (17)0.0002 (17)
C130.045 (2)0.059 (2)0.060 (3)−0.0018 (18)−0.0032 (19)0.006 (2)
C140.044 (2)0.053 (2)0.055 (2)−0.0082 (16)0.0048 (18)0.0032 (19)

Geometric parameters (Å, °)

Cl1—C31.732 (3)C4—C51.373 (5)
Cl2—C51.739 (3)C4—H4A0.93
O1—C71.352 (4)C5—C61.392 (4)
O1—N11.403 (4)C6—C71.458 (4)
O2—N31.207 (4)C8—C91.468 (4)
O3—N31.218 (4)C9—C141.384 (4)
N1—C81.302 (5)C9—C101.390 (4)
N2—C71.289 (4)C10—C111.378 (4)
N2—C81.366 (4)C10—H10A0.93
N3—C121.474 (5)C11—C121.377 (5)
C1—C21.383 (5)C11—H11A0.93
C1—C61.398 (4)C12—C131.371 (5)
C1—H1A0.93C13—C141.379 (5)
C2—C31.380 (5)C13—H13A0.93
C2—H2A0.93C14—H14A0.93
C3—C41.381 (5)
C7—O1—N1106.2 (2)N2—C7—O1112.3 (3)
C8—N1—O1103.8 (3)N2—C7—C6127.0 (3)
C7—N2—C8103.8 (3)O1—C7—C6120.7 (3)
O2—N3—O3123.6 (4)N1—C8—N2113.9 (3)
O2—N3—C12118.2 (3)N1—C8—C9122.5 (3)
O3—N3—C12118.2 (4)N2—C8—C9123.5 (3)
C2—C1—C6122.1 (3)C14—C9—C10119.4 (3)
C2—C1—H1A119.0C14—C9—C8119.0 (3)
C6—C1—H1A119.0C10—C9—C8121.6 (3)
C3—C2—C1118.4 (3)C11—C10—C9121.0 (3)
C3—C2—H2A120.8C11—C10—H10A119.5
C1—C2—H2A120.8C9—C10—H10A119.5
C2—C3—C4121.3 (3)C10—C11—C12118.0 (3)
C2—C3—Cl1119.6 (3)C10—C11—H11A121.0
C4—C3—Cl1119.1 (3)C12—C11—H11A121.0
C5—C4—C3119.1 (3)C13—C12—C11122.3 (3)
C5—C4—H4A120.4C13—C12—N3118.4 (3)
C3—C4—H4A120.4C11—C12—N3119.3 (3)
C4—C5—C6122.0 (3)C12—C13—C14119.2 (3)
C4—C5—Cl2115.8 (3)C12—C13—H13A120.4
C6—C5—Cl2122.1 (3)C14—C13—H13A120.4
C5—C6—C1117.0 (3)C13—C14—C9120.1 (3)
C5—C6—C7127.1 (3)C13—C14—H14A120.0
C1—C6—C7115.8 (3)C9—C14—H14A120.0
C7—O1—N1—C8−0.2 (4)O1—N1—C8—N20.1 (4)
C6—C1—C2—C3−0.3 (5)O1—N1—C8—C9−177.5 (3)
C1—C2—C3—C40.4 (5)C7—N2—C8—N10.2 (4)
C1—C2—C3—Cl1179.9 (3)C7—N2—C8—C9177.7 (3)
C2—C3—C4—C5−0.6 (5)N1—C8—C9—C14176.5 (4)
Cl1—C3—C4—C5179.9 (3)N2—C8—C9—C14−0.8 (5)
C3—C4—C5—C60.7 (5)N1—C8—C9—C10−2.4 (5)
C3—C4—C5—Cl2178.3 (3)N2—C8—C9—C10−179.7 (3)
C4—C5—C6—C1−0.6 (5)C14—C9—C10—C110.0 (5)
Cl2—C5—C6—C1−178.0 (3)C8—C9—C10—C11178.9 (3)
C4—C5—C6—C7178.5 (3)C9—C10—C11—C12−1.0 (5)
Cl2—C5—C6—C71.0 (5)C10—C11—C12—C130.6 (5)
C2—C1—C6—C50.4 (5)C10—C11—C12—N3−178.3 (3)
C2—C1—C6—C7−178.8 (3)O2—N3—C12—C13171.1 (4)
C8—N2—C7—O1−0.3 (4)O3—N3—C12—C13−9.9 (6)
C8—N2—C7—C6179.1 (3)O2—N3—C12—C11−9.9 (5)
N1—O1—C7—N20.4 (4)O3—N3—C12—C11169.0 (4)
N1—O1—C7—C6−179.1 (3)C11—C12—C13—C140.8 (6)
C5—C6—C7—N2−174.0 (4)N3—C12—C13—C14179.7 (3)
C1—C6—C7—N25.0 (5)C12—C13—C14—C9−1.8 (6)
C5—C6—C7—O15.3 (5)C10—C9—C14—C131.4 (6)
C1—C6—C7—O1−175.6 (3)C8—C9—C14—C13−177.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13A···N1i0.932.543.338 (5)144

Symmetry codes: (i) x+1/2, −y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5063).

References

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