Ethyl 5-methyl-3-phenyl-isoxazole-4-carboxyl-ate.

In the title compound, C13H13NO3, the dihedral angle between the phenyl and isoxazole rings is 43.40 (13)°. The eth-oxy-carbonyl group is rotated out of the plane of the isoxazole ring by 16.2 (13)°.

Related literature

For the biological and pharmacological importance of isoxazoles, see: Lin et al. (1997 ▶). For the synthesis of isoxazole derivatives and a related structure, see: Chandra et al. (2013 ▶).

Experimental

Crystal data

C13H13NO3

M = 231.24

Monoclinic,

a = 9.750 (8) Å

b = 14.589 (13) Å

c = 9.397 (8) Å

β = 116.872 (13)°

V = 1192.3 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

10036 measured reflections

2060 independent reflections

1340 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.186

S = 0.99

2060 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301427X/nc2309sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301427X/nc2309Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301427X/nc2309Isup3.cml

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

C13H13NO3	F(000) = 488
Mr = 231.24	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2060 reflections
a = 9.750 (8) Å	θ = 2.3–25.0°
b = 14.589 (13) Å	µ = 0.09 mm−1
c = 9.397 (8) Å	T = 273 K
β = 116.872 (13)°	Block, yellow
V = 1192.3 (18) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	Rint = 0.039
ω and φ scans	θmax = 25.0°, θmin = 2.3°
10036 measured reflections	h = −11→11
2060 independent reflections	k = −17→17
1340 reflections with I > 2σ(I)	l = −11→11

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1145P)2] where P = (Fo2 + 2Fc2)/3
2060 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O9	0.6154 (2)	0.13026 (13)	−0.1802 (3)	0.0780 (8)
O14	0.6825 (2)	0.12137 (19)	0.2907 (3)	0.1153 (12)
O15	0.4317 (2)	0.09643 (11)	0.17563 (19)	0.0667 (6)
N8	0.4554 (3)	0.14345 (15)	−0.2522 (3)	0.0747 (9)
C1	0.1443 (3)	0.10417 (18)	−0.3147 (3)	0.0721 (10)
C2	−0.0093 (3)	0.1141 (2)	−0.3603 (4)	0.0840 (11)
C3	−0.0594 (3)	0.1676 (2)	−0.2736 (4)	0.0861 (11)
C4	0.0469 (3)	0.21272 (19)	−0.1411 (4)	0.0798 (11)
C5	0.2008 (3)	0.20332 (16)	−0.0937 (3)	0.0649 (9)
C6	0.2520 (3)	0.14949 (15)	−0.1799 (3)	0.0571 (8)
C7	0.4161 (3)	0.13941 (14)	−0.1372 (3)	0.0577 (8)
C10	0.6666 (3)	0.11924 (16)	−0.0234 (3)	0.0646 (9)
C11	0.8327 (3)	0.0997 (2)	0.0691 (4)	0.0865 (11)
C12	0.5479 (3)	0.12501 (14)	0.0123 (3)	0.0592 (8)
C13	0.5628 (3)	0.11456 (17)	0.1739 (3)	0.0654 (9)
C16	0.4341 (4)	0.0912 (2)	0.3301 (3)	0.0824 (11)
C17	0.2752 (4)	0.0730 (2)	0.3043 (4)	0.0957 (14)
H1	0.17710	0.06700	−0.37380	0.0870*
H2	−0.08040	0.08420	−0.45110	0.1010*
H3	−0.16400	0.17340	−0.30390	0.1030*
H4	0.01350	0.25020	−0.08290	0.0950*
H5	0.27120	0.23350	−0.00280	0.0780*
H11A	0.85120	0.03600	0.05850	0.1300*
H11B	0.86540	0.11380	0.17950	0.1300*
H11C	0.88940	0.13650	0.02920	0.1300*
H16A	0.47100	0.14850	0.38720	0.0990*
H16B	0.50210	0.04240	0.39260	0.0990*
H17A	0.20880	0.12140	0.24150	0.1430*
H17B	0.27330	0.06990	0.40550	0.1430*
H17C	0.24040	0.01570	0.24930	0.1430*

	U11	U22	U33	U12	U13	U23
O9	0.0756 (13)	0.0937 (13)	0.0679 (14)	0.0024 (9)	0.0352 (11)	0.0109 (10)
O14	0.0684 (14)	0.196 (3)	0.0521 (14)	−0.0009 (13)	0.0015 (11)	−0.0013 (13)
O15	0.0746 (12)	0.0772 (11)	0.0415 (10)	−0.0015 (8)	0.0203 (9)	0.0048 (7)
N8	0.0768 (16)	0.0898 (15)	0.0555 (15)	0.0044 (11)	0.0281 (12)	0.0099 (11)
C1	0.0728 (18)	0.0765 (16)	0.0501 (16)	−0.0049 (12)	0.0129 (13)	−0.0015 (12)
C2	0.072 (2)	0.091 (2)	0.0633 (19)	−0.0137 (15)	0.0079 (16)	0.0049 (15)
C3	0.0632 (18)	0.091 (2)	0.092 (2)	0.0039 (15)	0.0245 (18)	0.0233 (18)
C4	0.081 (2)	0.0796 (17)	0.076 (2)	0.0125 (14)	0.0329 (16)	0.0104 (15)
C5	0.0744 (17)	0.0609 (14)	0.0497 (15)	0.0009 (11)	0.0195 (13)	0.0038 (11)
C6	0.0634 (15)	0.0558 (12)	0.0411 (14)	−0.0012 (10)	0.0139 (12)	0.0063 (10)
C7	0.0676 (16)	0.0533 (13)	0.0445 (15)	−0.0043 (10)	0.0186 (12)	0.0011 (10)
C10	0.0661 (16)	0.0592 (13)	0.0621 (18)	−0.0047 (11)	0.0234 (14)	0.0014 (11)
C11	0.0643 (18)	0.096 (2)	0.091 (2)	−0.0043 (14)	0.0279 (16)	0.0033 (16)
C12	0.0619 (15)	0.0555 (12)	0.0494 (15)	−0.0033 (10)	0.0157 (12)	0.0027 (10)
C13	0.0633 (17)	0.0723 (15)	0.0466 (16)	0.0026 (12)	0.0126 (13)	0.0014 (11)
C16	0.110 (2)	0.090 (2)	0.0457 (16)	0.0163 (16)	0.0338 (16)	0.0099 (13)
C17	0.121 (3)	0.098 (2)	0.090 (2)	0.0003 (18)	0.067 (2)	−0.0064 (18)

O9—N8	1.405 (4)	C12—C13	1.467 (4)
O9—C10	1.335 (4)	C16—C17	1.480 (6)
O14—C13	1.191 (4)	C1—H1	0.9300
O15—C13	1.313 (4)	C2—H2	0.9300
O15—C16	1.443 (4)	C3—H3	0.9300
N8—C7	1.301 (4)	C4—H4	0.9300
C1—C2	1.367 (5)	C5—H5	0.9300
C1—C6	1.394 (4)	C11—H11A	0.9600
C2—C3	1.368 (5)	C11—H11B	0.9600
C3—C4	1.375 (5)	C11—H11C	0.9600
C4—C5	1.366 (5)	C16—H16A	0.9700
C5—C6	1.374 (4)	C16—H16B	0.9700
C6—C7	1.470 (5)	C17—H17A	0.9600
C7—C12	1.427 (4)	C17—H17B	0.9600
C10—C11	1.479 (5)	C17—H17C	0.9600
C10—C12	1.345 (5)
O14···C2i	3.300 (5)	C5···H17Aiii	3.0100
O14···C11	3.056 (5)	C12···H5	3.0800
O15···C5	2.959 (4)	C13···H11B	2.9300
O15···C10ii	3.410 (4)	C13···H5	3.1000
O15···C6	3.089 (4)	C16···H16Bvii	3.0800
O9···H17Cii	2.7900	H1···N8	2.6700
O14···H16B	2.6200	H2···O14iv	2.5400
O14···H11B	2.4400	H4···H11Cvi	2.5500
O14···H16A	2.6300	H4···C1v	3.1000
O14···H2i	2.5400	H4···C2v	2.9600
O15···H5	2.6200	H5···O15	2.6200
N8···H1	2.6700	H5···C12	3.0800
N8···H5iii	2.8600	H5···C13	3.1000
C2···O14iv	3.300 (5)	H5···N8v	2.8600
C5···C17iii	3.567 (5)	H11B···O14	2.4400
C5···C13	3.526 (5)	H11B···C13	2.9300
C5···O15	2.959 (4)	H11C···C4viii	2.8900
C6···O15	3.089 (4)	H11C···H4viii	2.5500
C10···O15ii	3.410 (4)	H16A···O14	2.6300
C11···O14	3.056 (5)	H16B···O14	2.6200
C13···C5	3.526 (5)	H16B···C16vii	3.0800
C17···C5v	3.567 (5)	H16B···H16Bvii	2.3800
C1···H4iii	3.1000	H17A···C5v	3.0100
C2···H4iii	2.9600	H17C···O9ii	2.7900
C4···H11Cvi	2.8900
N8—O9—C10	109.1 (2)	C1—C2—H2	120.00
C13—O15—C16	116.7 (2)	C3—C2—H2	120.00
O9—N8—C7	105.9 (2)	C2—C3—H3	120.00
C2—C1—C6	120.2 (3)	C4—C3—H3	120.00
C1—C2—C3	120.6 (3)	C3—C4—H4	120.00
C2—C3—C4	119.1 (3)	C5—C4—H4	119.00
C3—C4—C5	121.0 (3)	C4—C5—H5	120.00
C4—C5—C6	120.2 (3)	C6—C5—H5	120.00
C1—C6—C5	118.8 (3)	C10—C11—H11A	109.00
C1—C6—C7	118.7 (2)	C10—C11—H11B	110.00
C5—C6—C7	122.5 (2)	C10—C11—H11C	109.00
N8—C7—C6	117.5 (2)	H11A—C11—H11B	109.00
N8—C7—C12	110.6 (3)	H11A—C11—H11C	109.00
C6—C7—C12	131.9 (3)	H11B—C11—H11C	109.00
O9—C10—C11	115.8 (3)	O15—C16—H16A	110.00
O9—C10—C12	109.5 (3)	O15—C16—H16B	110.00
C11—C10—C12	134.6 (3)	C17—C16—H16A	110.00
C7—C12—C10	104.9 (2)	C17—C16—H16B	110.00
C7—C12—C13	131.2 (3)	H16A—C16—H16B	108.00
C10—C12—C13	123.9 (3)	C16—C17—H17A	110.00
O14—C13—O15	124.0 (3)	C16—C17—H17B	109.00
O14—C13—C12	122.9 (3)	C16—C17—H17C	109.00
O15—C13—C12	113.1 (2)	H17A—C17—H17B	110.00
O15—C16—C17	107.8 (2)	H17A—C17—H17C	109.00
C2—C1—H1	120.00	H17B—C17—H17C	109.00
C6—C1—H1	120.00
C10—O9—N8—C7	−0.4 (3)	C1—C6—C7—N8	42.7 (3)
N8—O9—C10—C11	176.9 (2)	C1—C6—C7—C12	−137.0 (3)
N8—O9—C10—C12	−0.3 (3)	C5—C6—C7—N8	−136.0 (3)
C16—O15—C13—O14	4.6 (4)	C5—C6—C7—C12	44.3 (4)
C16—O15—C13—C12	−175.9 (2)	N8—C7—C12—C10	−1.1 (3)
C13—O15—C16—C17	178.4 (2)	N8—C7—C12—C13	−179.1 (2)
O9—N8—C7—C6	−178.90 (18)	C6—C7—C12—C10	178.7 (2)
O9—N8—C7—C12	0.9 (2)	C6—C7—C12—C13	0.7 (4)
C6—C1—C2—C3	−0.8 (4)	O9—C10—C12—C7	0.8 (3)
C2—C1—C6—C5	0.6 (4)	O9—C10—C12—C13	179.0 (2)
C2—C1—C6—C7	−178.2 (2)	C11—C10—C12—C7	−175.7 (3)
C1—C2—C3—C4	1.1 (5)	C11—C10—C12—C13	2.4 (4)
C2—C3—C4—C5	−1.3 (5)	C7—C12—C13—O14	−164.3 (3)
C3—C4—C5—C6	1.1 (4)	C7—C12—C13—O15	16.2 (3)
C4—C5—C6—C1	−0.7 (4)	C10—C12—C13—O14	18.0 (4)
C4—C5—C6—C7	178.0 (2)	C10—C12—C13—O15	−161.5 (2)