4-(4-Chloro-phen-yl)-5-phenyl-isoxazole.

The title compound, C(15)H(10)ClNO, is a functionalized isoxazole with a chloro-phenyl 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 = 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 ▶).

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

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

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 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)

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.

	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)*

	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)

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)