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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2324.
Published online 2009 September 5. doi:  10.1107/S1600536809034254
PMCID: PMC2970474

4-(4-Chloro­phen­yl)-5-phenyl­isoxazole

Abstract

The title compound, C15H10ClNO, is a functionalized isoxazole with a chloro­phenyl and a phenyl substitutent. The mean plane of the isoxazole ring is inclined to those of the two benzene ring mean planes by 38.32 (16) and 43.91 (18)°.

Related literature

For the chemistry and biological properties of isoxazoles, see: Bruno et al. (2004 [triangle]); Foti et al. (2004 [triangle]); He et al. (2000 [triangle]); Lakhvich et al. (1989 [triangle]); Lin et al. (1997 [triangle]); Makarov et al. (2005 [triangle]); Shipman (1995 [triangle]); Zhong et al. (2005 [triangle]). For related structures, see: Chang (2007 [triangle]); Tang et al. (2006 [triangle]); Zhang et al. (2006 [triangle]). For the synthesis, see: Subba Raju & Rao (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2324-scheme1.jpg

Experimental

Crystal data

  • C15H10ClNO
  • M r = 255.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2324-efi1.jpg
  • a = 6.554 (2) Å
  • b = 25.966 (2) Å
  • c = 7.4721 (19) Å
  • β = 106.171 (3)°
  • V = 1221.2 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 295 K
  • 0.3 × 0.2 × 0.2 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.928, T max = 0.952
  • 2820 measured reflections
  • 2132 independent reflections
  • 1851 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.197
  • S = 1.15
  • 2132 reflections
  • 204 parameters
  • All H-atom parameters refined
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker 2007 [triangle]); cell refinement: SAINT (Bruker 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: enCIFer (Allen et al., 2004 [triangle]) and PARST (Nardelli, 1995 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034254/su2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034254/su2135Isup2.hkl

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

Acknowledgments

MK thanks Ed. CEL, New Delhi, for sponsoring a visit to Yangon University, Myanmar.

supplementary crystallographic information

Comment

Isoxazoles are often used as pharmacophores in medicinal chemistry (Makarov et al., 2005). They are also important intermediates in the synthesis of many complex natural products (Lakhvich et al., 1989; Shipman, 1995). Recent synthetic efforts have established the importance of biologically active heterocyclic compounds (Foti et al., 2004). Of particular importance are the derivatives of isoxazoles representing one of the most active classes of compounds widely used in agrochemicals and pharmaceuticals (He et al., 2000). Such compounds have been studied from a synthetic (Bruno et al., 2004) and also from a structural viewpoint (Zhong et al., 2005). Isoxazole derivatives exhibit anticonvulsant, antibacterial, antiasthmatic, and other pharmacological activities (Lin et al., 1997). In this article, we report on the crystal structure of the title compound, 4-(4-chloro phenyl)-5-phenylisoxazole.

The molecular structute of the title compound is illustrated in Fig. 1 and the geometrical parameters are avilable in the archived CIF. The title compound is a functionalized isoxazole with a chlorophenyl and a phenyl substituent at positions 4 (C9) and 5 (C2), respectively, on the five-membered heterocyclic ring. They are inclined to the planar isoxazole ring mean plane by 38.32 (16)° and 43.91 (18)°, respectively. The torsion angles [C10-C9-C11-C12 = 38.4 (4)°, C2-C9-C11-C16 = 36.6 (5)°, O1-C2-C3-C4 = 44.1 (4)°, and C9-C2-C3-C8 = 43.7 (5)°)] confirm that these rings are twisted with respect to the plane of the isoxazole ring. The bond lengths of the isoxazole ring are normal and comparable to those reported for related structures: [3-(4-Chlorophenyl)isoxazol-5-yl]methanol (Tang et al., 2006), 3-(4-Chlorophenyl)isoxazole-5-carbaldehyde (Zhang et al., 2006), and 3-(2-Chlorophenyl)-N-methylisoxazole-5-carboxamide (Chang, 2007). However, bond length C2-C9 [1.359 (4) A°] is lengthened compared to the corresponding values in the above three related structures. {1.337 (3), 1.334 (3), 1.336 (3) Å, respectively}. This may be due to the steric effects caused by the substituents attached at atoms C2 and C9 on the isoxazole ring.

Experimental

The title compound was prepare according the the published procedure (Subba Raju & Rao, 1987). Recrystallization from n-hexane-benzene (1:1, v:v) by slow evaporation gave colourless block-like crystals suitable for X-ray diffraction analysis.

Refinement

All the H-atoms were clearly located in difference electron-density maps and were freely refined: C-H = 0.91 (5) - 1.00 (4) Å.

Figures

Fig. 1.
View of the molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level.

Crystal data

C15H10ClNOF(000) = 528
Mr = 255.69Dx = 1.391 Mg m3Dm = 1.39 Mg m3Dm measured by none
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 2895 reflections
a = 6.554 (2) Åθ = 2.4–25.0°
b = 25.966 (2) ŵ = 0.30 mm1
c = 7.4721 (19) ÅT = 295 K
β = 106.171 (3)°Block, colourless
V = 1221.2 (5) Å30.3 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker CCD diffractometer2132 independent reflections
Radiation source: fine-focus sealed tube1851 reflections with I > 2σ(I)
graphiteRint = 0.050
ω scansθmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −1→7
Tmin = 0.928, Tmax = 0.952k = −1→30
2820 measured reflectionsl = −8→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063All H-atom parameters refined
wR(F2) = 0.197w = 1/[σ2(Fo2) + (0.1057P)2 + 0.4763P] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.013
2132 reflectionsΔρmax = 0.27 e Å3
204 parametersΔρmin = −0.40 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (6)

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
N10.1131 (4)0.71167 (11)0.9809 (4)0.0706 (8)
O10.0578 (3)0.65915 (8)0.9619 (3)0.0655 (6)
C20.1585 (4)0.63669 (11)0.8469 (4)0.0539 (7)
C30.1165 (5)0.58171 (11)0.8114 (4)0.0592 (7)
C4−0.0886 (6)0.56265 (14)0.7745 (5)0.0757 (9)
C5−0.1270 (7)0.51065 (16)0.7433 (7)0.0921 (12)
C60.0349 (8)0.47763 (15)0.7496 (6)0.0913 (12)
C70.2396 (7)0.49578 (15)0.7837 (6)0.0865 (11)
C80.2801 (6)0.54770 (13)0.8143 (5)0.0710 (9)
C90.2800 (4)0.67225 (11)0.7910 (4)0.0524 (7)
C100.2441 (5)0.71820 (12)0.8794 (4)0.0632 (8)
C110.4076 (4)0.66740 (10)0.6569 (4)0.0506 (6)
C120.5940 (4)0.69549 (11)0.6830 (4)0.0560 (7)
C130.7069 (4)0.69393 (11)0.5508 (4)0.0587 (7)
C140.6323 (5)0.66396 (11)0.3947 (5)0.0596 (8)
Cl10.77032 (15)0.66286 (4)0.22763 (14)0.0817 (4)
C150.4495 (5)0.63545 (13)0.3666 (5)0.0641 (8)
C160.3369 (5)0.63760 (11)0.4988 (4)0.0586 (7)
H80.431 (7)0.5603 (15)0.846 (5)0.086 (11)*
H100.297 (5)0.7525 (13)0.865 (5)0.069 (9)*
H120.650 (5)0.7156 (13)0.801 (5)0.073 (10)*
H130.836 (6)0.7127 (13)0.568 (5)0.070 (9)*
H160.204 (6)0.6189 (14)0.476 (5)0.075 (9)*
H150.394 (6)0.6146 (16)0.256 (6)0.094 (12)*
H70.353 (7)0.4749 (18)0.780 (6)0.102 (13)*
H4−0.208 (6)0.5869 (15)0.763 (5)0.085 (11)*
H60.014 (7)0.4435 (19)0.723 (6)0.102 (13)*
H5−0.270 (8)0.4997 (19)0.722 (7)0.122 (17)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0793 (17)0.0725 (17)0.0737 (17)−0.0026 (12)0.0440 (14)−0.0121 (12)
O10.0685 (13)0.0744 (13)0.0670 (13)−0.0023 (10)0.0411 (10)−0.0038 (10)
C20.0534 (14)0.0615 (16)0.0551 (15)0.0020 (11)0.0289 (11)0.0019 (12)
C30.0649 (16)0.0626 (16)0.0607 (17)−0.0020 (12)0.0351 (13)0.0094 (12)
C40.0681 (19)0.074 (2)0.093 (3)−0.0085 (16)0.0371 (17)0.0076 (18)
C50.085 (2)0.081 (2)0.115 (3)−0.022 (2)0.036 (2)0.007 (2)
C60.119 (3)0.062 (2)0.097 (3)−0.013 (2)0.038 (2)0.0002 (19)
C70.100 (3)0.067 (2)0.102 (3)0.0114 (19)0.044 (2)0.0039 (18)
C80.0680 (19)0.0662 (19)0.088 (2)0.0002 (15)0.0364 (16)0.0052 (16)
C90.0507 (14)0.0587 (15)0.0550 (16)−0.0009 (11)0.0267 (11)0.0006 (11)
C100.0679 (17)0.0631 (17)0.0684 (19)−0.0038 (13)0.0349 (14)−0.0058 (14)
C110.0521 (14)0.0517 (14)0.0565 (16)0.0007 (10)0.0291 (12)0.0026 (11)
C120.0555 (15)0.0555 (14)0.0653 (18)−0.0009 (11)0.0307 (13)0.0018 (13)
C130.0517 (15)0.0607 (16)0.0726 (19)0.0001 (12)0.0322 (13)0.0093 (14)
C140.0620 (16)0.0608 (16)0.069 (2)0.0128 (12)0.0403 (14)0.0125 (13)
Cl10.0872 (7)0.0946 (7)0.0854 (7)0.0188 (4)0.0606 (5)0.0153 (4)
C150.0730 (19)0.0686 (18)0.0605 (18)0.0039 (14)0.0348 (14)−0.0036 (14)
C160.0591 (16)0.0638 (17)0.0609 (17)−0.0087 (13)0.0300 (13)−0.0042 (13)

Geometric parameters (Å, °)

N1—C101.306 (4)C8—H81.00 (4)
N1—O11.408 (3)C9—C101.415 (4)
O1—C21.353 (3)C9—C111.478 (4)
C2—C91.359 (4)C10—H100.97 (3)
C2—C31.464 (4)C11—C161.380 (4)
C3—C81.385 (4)C11—C121.389 (4)
C3—C41.386 (5)C12—C131.390 (4)
C4—C51.381 (6)C12—H121.00 (4)
C4—H40.99 (4)C13—C141.374 (5)
C5—C61.355 (6)C13—H130.96 (4)
C5—H50.95 (5)C14—C151.374 (5)
C6—C71.377 (6)C14—Cl11.734 (3)
C6—H60.91 (5)C15—C161.389 (4)
C7—C81.381 (5)C15—H150.97 (4)
C7—H70.92 (5)C16—H160.97 (4)
C10—N1—O1105.0 (2)C2—C9—C11129.8 (3)
C2—O1—N1108.9 (2)C10—C9—C11125.9 (2)
O1—C2—C9109.5 (2)N1—C10—C9112.5 (3)
O1—C2—C3115.8 (2)N1—C10—H10120 (2)
C9—C2—C3134.8 (3)C9—C10—H10128 (2)
C8—C3—C4118.6 (3)C16—C11—C12119.2 (3)
C8—C3—C2120.9 (3)C16—C11—C9120.6 (2)
C4—C3—C2120.5 (3)C12—C11—C9120.1 (3)
C5—C4—C3120.2 (4)C11—C12—C13120.4 (3)
C5—C4—H4120 (2)C11—C12—H12119 (2)
C3—C4—H4119 (2)C13—C12—H12120 (2)
C6—C5—C4120.6 (4)C14—C13—C12119.1 (3)
C6—C5—H5123 (3)C14—C13—H13120 (2)
C4—C5—H5116 (3)C12—C13—H13121 (2)
C5—C6—C7120.2 (4)C13—C14—C15121.6 (3)
C5—C6—H6123 (3)C13—C14—Cl1119.1 (2)
C7—C6—H6117 (3)C15—C14—Cl1119.3 (3)
C6—C7—C8119.8 (4)C14—C15—C16118.9 (3)
C6—C7—H7123 (3)C14—C15—H15122 (2)
C8—C7—H7117 (3)C16—C15—H15119 (2)
C7—C8—C3120.5 (3)C11—C16—C15120.9 (3)
C7—C8—H8119 (2)C11—C16—H16120 (2)
C3—C8—H8120 (2)C15—C16—H16119 (2)
C2—C9—C10104.0 (2)
C10—N1—O1—C2−0.6 (3)C3—C2—C9—C114.8 (6)
N1—O1—C2—C90.7 (3)O1—N1—C10—C90.3 (4)
N1—O1—C2—C3−179.6 (2)C2—C9—C10—N10.1 (4)
O1—C2—C3—C8−135.8 (3)C11—C9—C10—N1175.5 (3)
C9—C2—C3—C843.7 (5)C2—C9—C11—C1636.6 (5)
O1—C2—C3—C444.1 (4)C10—C9—C11—C16−137.5 (3)
C9—C2—C3—C4−136.4 (4)C2—C9—C11—C12−147.5 (3)
C8—C3—C4—C50.7 (5)C10—C9—C11—C1238.4 (4)
C2—C3—C4—C5−179.2 (4)C16—C11—C12—C130.5 (4)
C3—C4—C5—C60.4 (7)C9—C11—C12—C13−175.4 (3)
C4—C5—C6—C7−1.2 (7)C11—C12—C13—C14−0.4 (4)
C5—C6—C7—C81.0 (7)C12—C13—C14—C15−0.2 (4)
C6—C7—C8—C30.2 (6)C12—C13—C14—Cl1178.9 (2)
C4—C3—C8—C7−1.0 (5)C13—C14—C15—C160.7 (5)
C2—C3—C8—C7179.0 (3)Cl1—C14—C15—C16−178.4 (2)
O1—C2—C9—C10−0.5 (3)C12—C11—C16—C150.0 (4)
C3—C2—C9—C10179.9 (3)C9—C11—C16—C15175.9 (3)
O1—C2—C9—C11−175.6 (3)C14—C15—C16—C11−0.6 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2135).

References

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