4-(4-Chloro­phen­yl)-5-phenyl­isoxazole

Krishnaiah, M.; Ravi Kumar, R.; Oo, T.; Kaung, P.

doi:10.1107/S1600536809034254

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2324

doi:10.1107/S1600536809034254

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4-(4-Chlorophenyl)-5-phenylisoxazole

M. Krishnaiah,^a R. Ravi Kumar,^a Thanzaw Oo ^b ^* and Pho Kaung ^b

^aDepartment of Physics, SV University, Tirupati 517502, India, and ^bDepartment of Physics, Yangon University, Myanmar
^*Correspondence e-mail: Thanzawoo06@gmail.com

(Received 5 August 2009; accepted 26 August 2009; online 5 September 2009)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.063
wR(F²) = 0.197
S = 1.15
2132 reflections
204 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 & Rao (1987).

Experimental top

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.

Computing details top

Data collection: SMART (Bruker 2007); cell refinement: SAINT (Bruker 2007); data reduction: SAINT (Bruker 2007); 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).

Figures top

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.

4-(4-Chlorophenyl)-5-phenylisoxazole top

Crystal data top

C₁₅H₁₀ClNO	F(000) = 528
M_r = 255.69	D_x = 1.391 Mg m⁻³ D_m = 1.39 Mg m⁻³ D_m 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 top

Bruker CCD diffractometer	2132 independent reflections
Radiation source: fine-focus sealed tube	1851 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −1→7
T_min = 0.928, T_max = 0.952	k = −1→30
2820 measured reflections	l = −8→8

Refinement top

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(F_o²) + (0.1057P)² + 0.4763P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.013
2132 reflections	Δρ_max = 0.27 e Å⁻³
204 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₀ClNO	V = 1221.2 (5) Å³
M_r = 255.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.554 (2) Å	µ = 0.30 mm⁻¹
b = 25.966 (2) Å	T = 295 K
c = 7.4721 (19) Å	0.3 × 0.2 × 0.2 mm
β = 106.171 (3)°

Data collection top

Bruker CCD diffractometer	2132 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1851 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.952	R_int = 0.050
2820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.197	All H-atom parameters refined
S = 1.15	Δρ_max = 0.27 e Å⁻³
2132 reflections	Δρ_min = −0.40 e Å⁻³
204 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClNO
M_r	255.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.554 (2), 25.966 (2), 7.4721 (19)
β (°)	106.171 (3)
V (Å³)	1221.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Bruker CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.928, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	2820, 2132, 1851
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.197, 1.15
No. of reflections	2132
No. of parameters	204
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.40

Computer programs: SMART (Bruker 2007), SAINT (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), enCIFer (Allen et al., 2004) and PARST (Nardelli, 1995).

Acknowledgements

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

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