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 ▶); Foti et al. (2004 ▶); He et al. (2000 ▶); Lakhvich et al. (1989 ▶); Lin et al. (1997 ▶); Makarov et al. (2005 ▶); Shipman (1995 ▶); Zhong et al. (2005 ▶). For related structures, see: Chang (2007 ▶); Tang et al. (2006 ▶); Zhang et al. (2006 ▶). For the synthesis, see: Subba Raju & Rao (1987 ▶). 
Experimental
Crystal data
C15H10ClNO
M r = 255.69
Monoclinic,
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 ▶) 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 ▶); cell refinement: SAINT (Bruker 2007 ▶); 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 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and PARST (Nardelli, 1995 ▶).
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
| C15H10ClNO | F(000) = 528 |
| Mr = 255.69 | Dx = 1.391 Mg m−3Dm = 1.39 Mg m−3Dm measured by none |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2895 reflections |
| a = 6.554 (2) Å | θ = 2.4–25.0° |
| b = 25.966 (2) Å | µ = 0.30 mm−1 |
| c = 7.4721 (19) Å | T = 295 K |
| β = 106.171 (3)° | Block, colourless |
| V = 1221.2 (5) Å3 | 0.3 × 0.2 × 0.2 mm |
| Z = 4 |
Data collection
| Bruker CCD diffractometer | 2132 independent reflections |
| Radiation source: fine-focus sealed tube | 1851 reflections with I > 2σ(I) |
| graphite | Rint = 0.050 |
| ω scans | θmax = 25.0°, θmin = 2.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −1→7 |
| Tmin = 0.928, Tmax = 0.952 | k = −1→30 |
| 2820 measured reflections | l = −8→8 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.063 | All H-atom parameters refined |
| wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.1057P)2 + 0.4763P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.15 | (Δ/σ)max = 0.013 |
| 2132 reflections | Δρmax = 0.27 e Å−3 |
| 204 parameters | Δρmin = −0.40 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction 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)
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.1131 (4) | 0.71167 (11) | 0.9809 (4) | 0.0706 (8) | |
| O1 | 0.0578 (3) | 0.65915 (8) | 0.9619 (3) | 0.0655 (6) | |
| C2 | 0.1585 (4) | 0.63669 (11) | 0.8469 (4) | 0.0539 (7) | |
| C3 | 0.1165 (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) | |
| C6 | 0.0349 (8) | 0.47763 (15) | 0.7496 (6) | 0.0913 (12) | |
| C7 | 0.2396 (7) | 0.49578 (15) | 0.7837 (6) | 0.0865 (11) | |
| C8 | 0.2801 (6) | 0.54770 (13) | 0.8143 (5) | 0.0710 (9) | |
| C9 | 0.2800 (4) | 0.67225 (11) | 0.7910 (4) | 0.0524 (7) | |
| C10 | 0.2441 (5) | 0.71820 (12) | 0.8794 (4) | 0.0632 (8) | |
| C11 | 0.4076 (4) | 0.66740 (10) | 0.6569 (4) | 0.0506 (6) | |
| C12 | 0.5940 (4) | 0.69549 (11) | 0.6830 (4) | 0.0560 (7) | |
| C13 | 0.7069 (4) | 0.69393 (11) | 0.5508 (4) | 0.0587 (7) | |
| C14 | 0.6323 (5) | 0.66396 (11) | 0.3947 (5) | 0.0596 (8) | |
| Cl1 | 0.77032 (15) | 0.66286 (4) | 0.22763 (14) | 0.0817 (4) | |
| C15 | 0.4495 (5) | 0.63545 (13) | 0.3666 (5) | 0.0641 (8) | |
| C16 | 0.3369 (5) | 0.63760 (11) | 0.4988 (4) | 0.0586 (7) | |
| H8 | 0.431 (7) | 0.5603 (15) | 0.846 (5) | 0.086 (11)* | |
| H10 | 0.297 (5) | 0.7525 (13) | 0.865 (5) | 0.069 (9)* | |
| H12 | 0.650 (5) | 0.7156 (13) | 0.801 (5) | 0.073 (10)* | |
| H13 | 0.836 (6) | 0.7127 (13) | 0.568 (5) | 0.070 (9)* | |
| H16 | 0.204 (6) | 0.6189 (14) | 0.476 (5) | 0.075 (9)* | |
| H15 | 0.394 (6) | 0.6146 (16) | 0.256 (6) | 0.094 (12)* | |
| H7 | 0.353 (7) | 0.4749 (18) | 0.780 (6) | 0.102 (13)* | |
| H4 | −0.208 (6) | 0.5869 (15) | 0.763 (5) | 0.085 (11)* | |
| H6 | 0.014 (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)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0793 (17) | 0.0725 (17) | 0.0737 (17) | −0.0026 (12) | 0.0440 (14) | −0.0121 (12) |
| O1 | 0.0685 (13) | 0.0744 (13) | 0.0670 (13) | −0.0023 (10) | 0.0411 (10) | −0.0038 (10) |
| C2 | 0.0534 (14) | 0.0615 (16) | 0.0551 (15) | 0.0020 (11) | 0.0289 (11) | 0.0019 (12) |
| C3 | 0.0649 (16) | 0.0626 (16) | 0.0607 (17) | −0.0020 (12) | 0.0351 (13) | 0.0094 (12) |
| C4 | 0.0681 (19) | 0.074 (2) | 0.093 (3) | −0.0085 (16) | 0.0371 (17) | 0.0076 (18) |
| C5 | 0.085 (2) | 0.081 (2) | 0.115 (3) | −0.022 (2) | 0.036 (2) | 0.007 (2) |
| C6 | 0.119 (3) | 0.062 (2) | 0.097 (3) | −0.013 (2) | 0.038 (2) | 0.0002 (19) |
| C7 | 0.100 (3) | 0.067 (2) | 0.102 (3) | 0.0114 (19) | 0.044 (2) | 0.0039 (18) |
| C8 | 0.0680 (19) | 0.0662 (19) | 0.088 (2) | 0.0002 (15) | 0.0364 (16) | 0.0052 (16) |
| C9 | 0.0507 (14) | 0.0587 (15) | 0.0550 (16) | −0.0009 (11) | 0.0267 (11) | 0.0006 (11) |
| C10 | 0.0679 (17) | 0.0631 (17) | 0.0684 (19) | −0.0038 (13) | 0.0349 (14) | −0.0058 (14) |
| C11 | 0.0521 (14) | 0.0517 (14) | 0.0565 (16) | 0.0007 (10) | 0.0291 (12) | 0.0026 (11) |
| C12 | 0.0555 (15) | 0.0555 (14) | 0.0653 (18) | −0.0009 (11) | 0.0307 (13) | 0.0018 (13) |
| C13 | 0.0517 (15) | 0.0607 (16) | 0.0726 (19) | 0.0001 (12) | 0.0322 (13) | 0.0093 (14) |
| C14 | 0.0620 (16) | 0.0608 (16) | 0.069 (2) | 0.0128 (12) | 0.0403 (14) | 0.0125 (13) |
| Cl1 | 0.0872 (7) | 0.0946 (7) | 0.0854 (7) | 0.0188 (4) | 0.0606 (5) | 0.0153 (4) |
| C15 | 0.0730 (19) | 0.0686 (18) | 0.0605 (18) | 0.0039 (14) | 0.0348 (14) | −0.0036 (14) |
| C16 | 0.0591 (16) | 0.0638 (17) | 0.0609 (17) | −0.0087 (13) | 0.0300 (13) | −0.0042 (13) |
Geometric parameters (Å, °)
| N1—C10 | 1.306 (4) | C8—H8 | 1.00 (4) |
| N1—O1 | 1.408 (3) | C9—C10 | 1.415 (4) |
| O1—C2 | 1.353 (3) | C9—C11 | 1.478 (4) |
| C2—C9 | 1.359 (4) | C10—H10 | 0.97 (3) |
| C2—C3 | 1.464 (4) | C11—C16 | 1.380 (4) |
| C3—C8 | 1.385 (4) | C11—C12 | 1.389 (4) |
| C3—C4 | 1.386 (5) | C12—C13 | 1.390 (4) |
| C4—C5 | 1.381 (6) | C12—H12 | 1.00 (4) |
| C4—H4 | 0.99 (4) | C13—C14 | 1.374 (5) |
| C5—C6 | 1.355 (6) | C13—H13 | 0.96 (4) |
| C5—H5 | 0.95 (5) | C14—C15 | 1.374 (5) |
| C6—C7 | 1.377 (6) | C14—Cl1 | 1.734 (3) |
| C6—H6 | 0.91 (5) | C15—C16 | 1.389 (4) |
| C7—C8 | 1.381 (5) | C15—H15 | 0.97 (4) |
| C7—H7 | 0.92 (5) | C16—H16 | 0.97 (4) |
| C10—N1—O1 | 105.0 (2) | C2—C9—C11 | 129.8 (3) |
| C2—O1—N1 | 108.9 (2) | C10—C9—C11 | 125.9 (2) |
| O1—C2—C9 | 109.5 (2) | N1—C10—C9 | 112.5 (3) |
| O1—C2—C3 | 115.8 (2) | N1—C10—H10 | 120 (2) |
| C9—C2—C3 | 134.8 (3) | C9—C10—H10 | 128 (2) |
| C8—C3—C4 | 118.6 (3) | C16—C11—C12 | 119.2 (3) |
| C8—C3—C2 | 120.9 (3) | C16—C11—C9 | 120.6 (2) |
| C4—C3—C2 | 120.5 (3) | C12—C11—C9 | 120.1 (3) |
| C5—C4—C3 | 120.2 (4) | C11—C12—C13 | 120.4 (3) |
| C5—C4—H4 | 120 (2) | C11—C12—H12 | 119 (2) |
| C3—C4—H4 | 119 (2) | C13—C12—H12 | 120 (2) |
| C6—C5—C4 | 120.6 (4) | C14—C13—C12 | 119.1 (3) |
| C6—C5—H5 | 123 (3) | C14—C13—H13 | 120 (2) |
| C4—C5—H5 | 116 (3) | C12—C13—H13 | 121 (2) |
| C5—C6—C7 | 120.2 (4) | C13—C14—C15 | 121.6 (3) |
| C5—C6—H6 | 123 (3) | C13—C14—Cl1 | 119.1 (2) |
| C7—C6—H6 | 117 (3) | C15—C14—Cl1 | 119.3 (3) |
| C6—C7—C8 | 119.8 (4) | C14—C15—C16 | 118.9 (3) |
| C6—C7—H7 | 123 (3) | C14—C15—H15 | 122 (2) |
| C8—C7—H7 | 117 (3) | C16—C15—H15 | 119 (2) |
| C7—C8—C3 | 120.5 (3) | C11—C16—C15 | 120.9 (3) |
| C7—C8—H8 | 119 (2) | C11—C16—H16 | 120 (2) |
| C3—C8—H8 | 120 (2) | C15—C16—H16 | 119 (2) |
| C2—C9—C10 | 104.0 (2) | ||
| C10—N1—O1—C2 | −0.6 (3) | C3—C2—C9—C11 | 4.8 (6) |
| N1—O1—C2—C9 | 0.7 (3) | O1—N1—C10—C9 | 0.3 (4) |
| N1—O1—C2—C3 | −179.6 (2) | C2—C9—C10—N1 | 0.1 (4) |
| O1—C2—C3—C8 | −135.8 (3) | C11—C9—C10—N1 | 175.5 (3) |
| C9—C2—C3—C8 | 43.7 (5) | C2—C9—C11—C16 | 36.6 (5) |
| O1—C2—C3—C4 | 44.1 (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—C5 | 0.7 (5) | C10—C9—C11—C12 | 38.4 (4) |
| C2—C3—C4—C5 | −179.2 (4) | C16—C11—C12—C13 | 0.5 (4) |
| C3—C4—C5—C6 | 0.4 (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—C8 | 1.0 (7) | C12—C13—C14—C15 | −0.2 (4) |
| C6—C7—C8—C3 | 0.2 (6) | C12—C13—C14—Cl1 | 178.9 (2) |
| C4—C3—C8—C7 | −1.0 (5) | C13—C14—C15—C16 | 0.7 (5) |
| C2—C3—C8—C7 | 179.0 (3) | Cl1—C14—C15—C16 | −178.4 (2) |
| O1—C2—C9—C10 | −0.5 (3) | C12—C11—C16—C15 | 0.0 (4) |
| C3—C2—C9—C10 | 179.9 (3) | C9—C11—C16—C15 | 175.9 (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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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
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