5-(3-Methyl-phen-yl)-3-phenyl-1,2-oxazole.

In the title compound, C(16)H(13)NO, the isoxazole ring makes dihedral angles of 16.64 (7)° with 3-methyl-phenzyl ring and 17.60 (7)° with the unsubstituted phenyl ring.

Related literature

For general background to isoxazole derivatives, see: Sperry & Wright (2005 ▶); Krogsgaard-Larsen et al. (1996 ▶); Deng et al. (2009 ▶); Talley (1999 ▶).

Experimental

Crystal data

C16H13NO

M = 235.27

Orthorhombic,

a = 5.8052 (2) Å

b = 7.7010 (3) Å

c = 27.4363 (8) Å

V = 1226.56 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.984

14583 measured reflections

1599 independent reflections

1302 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.08

1599 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020198/bt5513sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020198/bt5513Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020198/bt5513Isup3.cml

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

C16H13NO	Dx = 1.274 Mg m−3
Mr = 235.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 14583 reflections
a = 5.8052 (2) Å	θ = 1.5–27.1°
b = 7.7010 (3) Å	µ = 0.08 mm−1
c = 27.4363 (8) Å	T = 293 K
V = 1226.56 (7) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm
F(000) = 496

Bruker Kappa APEXII area-detector diffractometer	1599 independent reflections
Radiation source: fine-focus sealed tube	1302 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→6
Tmin = 0.977, Tmax = 0.984	k = −8→9
14583 measured reflections	l = −35→35

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.1446P] where P = (Fo2 + 2Fc2)/3
1599 reflections	(Δ/σ)max = 0.003
164 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
N	0.3214 (3)	0.4492 (3)	0.09265 (7)	0.0550 (5)
O	0.3690 (3)	0.3988 (3)	0.14108 (6)	0.0662 (5)
C9	0.5947 (4)	0.3630 (3)	0.14404 (8)	0.0492 (6)
C10	0.6819 (4)	0.3105 (3)	0.19162 (8)	0.0471 (5)
C14	0.6336 (4)	0.2897 (3)	0.27920 (8)	0.0498 (5)
C7	0.5182 (4)	0.4406 (3)	0.06915 (8)	0.0505 (5)
C15	0.5545 (4)	0.3395 (3)	0.23393 (8)	0.0491 (5)
H15	0.4121	0.3941	0.2315	0.059*
C13	0.8460 (4)	0.2078 (3)	0.28208 (9)	0.0553 (6)
H13	0.9016	0.1721	0.3123	0.066*
C8	0.6941 (4)	0.3875 (3)	0.09969 (8)	0.0526 (6)
H8	0.8483	0.3718	0.0916	0.063*
C1	0.7032 (5)	0.4368 (3)	−0.01203 (9)	0.0650 (7)
H1	0.8257	0.3757	0.0015	0.078*
C12	0.9760 (5)	0.1786 (3)	0.24080 (10)	0.0603 (6)
H12	1.1181	0.1237	0.2434	0.072*
C11	0.8968 (4)	0.2303 (3)	0.19575 (10)	0.0556 (6)
H11	0.9863	0.2119	0.1681	0.067*
C6	0.5200 (4)	0.4874 (3)	0.01707 (8)	0.0506 (5)
C5	0.3401 (5)	0.5778 (3)	−0.00369 (9)	0.0627 (7)
H5	0.2162	0.6123	0.0155	0.075*
C16	0.4918 (5)	0.3241 (4)	0.32435 (9)	0.0708 (8)
H16A	0.4844	0.4469	0.3302	0.106*
H16B	0.5620	0.2679	0.3518	0.106*
H16C	0.3390	0.2795	0.3198	0.106*
C4	0.3426 (5)	0.6172 (4)	−0.05246 (10)	0.0718 (8)
H4	0.2208	0.6784	−0.0662	0.086*
C3	0.5239 (5)	0.5667 (4)	−0.08088 (10)	0.0739 (8)
H3	0.5248	0.5934	−0.1139	0.089*
C2	0.7041 (6)	0.4771 (4)	−0.06096 (10)	0.0728 (8)
H2	0.8272	0.4432	−0.0804	0.087*

	U11	U22	U33	U12	U13	U23
N	0.0399 (10)	0.0734 (13)	0.0517 (11)	0.0032 (11)	0.0004 (9)	0.0030 (10)
O	0.0460 (9)	0.0866 (13)	0.0659 (11)	0.0012 (10)	0.0061 (9)	0.0003 (10)
C9	0.0397 (11)	0.0458 (12)	0.0622 (14)	−0.0024 (10)	0.0069 (10)	−0.0042 (11)
C10	0.0386 (10)	0.0410 (10)	0.0618 (13)	−0.0057 (10)	0.0035 (11)	−0.0007 (10)
C14	0.0464 (12)	0.0423 (11)	0.0607 (13)	−0.0042 (10)	0.0005 (11)	0.0011 (10)
C7	0.0461 (12)	0.0453 (11)	0.0599 (13)	−0.0042 (11)	0.0024 (11)	−0.0036 (10)
C15	0.0414 (12)	0.0426 (11)	0.0634 (14)	0.0008 (10)	0.0032 (10)	0.0021 (10)
C13	0.0481 (12)	0.0482 (12)	0.0696 (15)	−0.0022 (12)	−0.0060 (12)	0.0048 (11)
C8	0.0405 (11)	0.0570 (14)	0.0604 (14)	0.0020 (11)	0.0069 (11)	0.0016 (11)
C1	0.0630 (16)	0.0617 (15)	0.0702 (17)	0.0093 (14)	0.0084 (14)	0.0007 (13)
C12	0.0431 (12)	0.0516 (13)	0.0862 (18)	0.0046 (11)	−0.0021 (13)	0.0033 (13)
C11	0.0423 (11)	0.0507 (13)	0.0739 (16)	−0.0010 (11)	0.0092 (11)	−0.0019 (12)
C6	0.0500 (13)	0.0459 (11)	0.0558 (13)	−0.0033 (11)	0.0016 (11)	−0.0053 (10)
C5	0.0538 (14)	0.0686 (16)	0.0658 (16)	0.0088 (14)	−0.0002 (13)	−0.0047 (12)
C16	0.0697 (17)	0.0822 (19)	0.0605 (14)	0.0098 (17)	−0.0012 (14)	−0.0001 (14)
C4	0.0721 (18)	0.0784 (18)	0.0648 (16)	0.0102 (17)	−0.0104 (15)	−0.0002 (14)
C3	0.095 (2)	0.0701 (17)	0.0569 (15)	0.0028 (18)	−0.0021 (16)	−0.0022 (13)
C2	0.0784 (19)	0.0758 (18)	0.0644 (16)	0.0096 (17)	0.0163 (15)	−0.0032 (14)

N—C7	1.314 (3)	C1—C6	1.386 (3)
N—O	1.412 (2)	C1—H1	0.9300
O—C9	1.341 (3)	C12—C11	1.378 (3)
C9—C8	1.360 (3)	C12—H12	0.9300
C9—C10	1.457 (3)	C11—H11	0.9300
C10—C15	1.394 (3)	C6—C5	1.378 (3)
C10—C11	1.397 (3)	C5—C4	1.372 (4)
C14—C15	1.379 (3)	C5—H5	0.9300
C14—C13	1.387 (3)	C16—H16A	0.9600
C14—C16	1.511 (3)	C16—H16B	0.9600
C7—C8	1.383 (3)	C16—H16C	0.9600
C7—C6	1.474 (3)	C4—C3	1.366 (4)
C15—H15	0.9300	C4—H4	0.9300
C13—C12	1.379 (4)	C3—C2	1.367 (4)
C13—H13	0.9300	C3—H3	0.9300
C8—H8	0.9300	C2—H2	0.9300
C1—C2	1.378 (4)
C7—N—O	106.11 (18)	C11—C12—H12	119.8
C9—O—N	107.76 (18)	C13—C12—H12	119.8
O—C9—C8	109.4 (2)	C12—C11—C10	119.9 (2)
O—C9—C10	116.8 (2)	C12—C11—H11	120.0
C8—C9—C10	133.8 (2)	C10—C11—H11	120.0
C15—C10—C11	118.5 (2)	C5—C6—C1	119.0 (2)
C15—C10—C9	121.2 (2)	C5—C6—C7	121.3 (2)
C11—C10—C9	120.4 (2)	C1—C6—C7	119.7 (2)
C15—C14—C13	118.3 (2)	C4—C5—C6	120.4 (2)
C15—C14—C16	120.6 (2)	C4—C5—H5	119.8
C13—C14—C16	121.2 (2)	C6—C5—H5	119.8
N—C7—C8	111.1 (2)	C14—C16—H16A	109.5
N—C7—C6	118.0 (2)	C14—C16—H16B	109.5
C8—C7—C6	130.9 (2)	H16A—C16—H16B	109.5
C14—C15—C10	121.9 (2)	C14—C16—H16C	109.5
C14—C15—H15	119.0	H16A—C16—H16C	109.5
C10—C15—H15	119.0	H16B—C16—H16C	109.5
C12—C13—C14	120.9 (2)	C3—C4—C5	120.1 (3)
C12—C13—H13	119.5	C3—C4—H4	119.9
C14—C13—H13	119.5	C5—C4—H4	119.9
C9—C8—C7	105.7 (2)	C4—C3—C2	120.3 (3)
C9—C8—H8	127.2	C4—C3—H3	119.8
C7—C8—H8	127.2	C2—C3—H3	119.8
C2—C1—C6	120.1 (3)	C3—C2—C1	120.0 (3)
C2—C1—H1	120.0	C3—C2—H2	120.0
C6—C1—H1	120.0	C1—C2—H2	120.0
C11—C12—C13	120.5 (2)
C7—N—O—C9	0.3 (3)	C6—C7—C8—C9	179.6 (2)
N—O—C9—C8	−0.2 (3)	C14—C13—C12—C11	−0.1 (4)
N—O—C9—C10	179.04 (18)	C13—C12—C11—C10	−1.0 (4)
O—C9—C10—C15	−16.3 (3)	C15—C10—C11—C12	1.4 (3)
C8—C9—C10—C15	162.8 (3)	C9—C10—C11—C12	−178.9 (2)
O—C9—C10—C11	164.0 (2)	C2—C1—C6—C5	0.1 (4)
C8—C9—C10—C11	−16.9 (4)	C2—C1—C6—C7	178.7 (3)
O—N—C7—C8	−0.2 (3)	N—C7—C6—C5	16.0 (3)
O—N—C7—C6	−179.81 (18)	C8—C7—C6—C5	−163.5 (3)
C13—C14—C15—C10	−0.3 (3)	N—C7—C6—C1	−162.6 (2)
C16—C14—C15—C10	179.6 (2)	C8—C7—C6—C1	17.9 (4)
C11—C10—C15—C14	−0.8 (3)	C1—C6—C5—C4	−0.1 (4)
C9—C10—C15—C14	179.6 (2)	C7—C6—C5—C4	−178.7 (2)
C15—C14—C13—C12	0.7 (3)	C6—C5—C4—C3	0.1 (4)
C16—C14—C13—C12	−179.2 (2)	C5—C4—C3—C2	−0.2 (4)
O—C9—C8—C7	0.1 (3)	C4—C3—C2—C1	0.2 (4)
C10—C9—C8—C7	−179.0 (2)	C6—C1—C2—C3	−0.1 (4)
N—C7—C8—C9	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O	0.93	2.49	2.803 (3)	100.