Isopropyl 3-phenyl-isoxazole-5-carboxyl-ate.

In the title compound, C13H13NO3, the isoxazole ring is approximately coplanar with the phenyl ring, the dihedral angle between their planes being 7.37 (19)°. In the crystal, centrosymmetrically related mol-ecules are linked into dimers by pairs of C-H⋯O hydrogen bonds, generating a ring of graph-set motif R 2 (2)(10).

Related literature

For the biological activity of isoxazole derivatives, see: Angibaud et al. (2003 ▶). For the structure of a related compound, see: Yao & Deng (2008 ▶). For the synthesis of 3-phenyl­isoxazole-5-carb­oxy­lic acid, see: Liu et al. (2006 ▶).

Experimental

Crystal data

C13H13NO3

M = 231.24

Monoclinic,

a = 4.6311 (10) Å

b = 16.596 (4) Å

c = 15.897 (3) Å

β = 98.321 (4)°

V = 1208.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.36 × 0.28 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.968, T max = 0.984

6039 measured reflections

2169 independent reflections

1511 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.03

2169 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009392/rz5055sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009392/rz5055Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009392/rz5055Isup3.cml

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

C13H13NO3	F(000) = 488
Mr = 231.24	Dx = 1.271 Mg m−3Dm = 1.270 Mg m−3Dm measured by not measured
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1178 reflections
a = 4.6311 (10) Å	θ = 2.5–21.2°
b = 16.596 (4) Å	µ = 0.09 mm−1
c = 15.897 (3) Å	T = 296 K
β = 98.321 (4)°	Block, colourless
V = 1208.9 (5) Å3	0.36 × 0.28 × 0.17 mm
Z = 4

Bruker APEXII CCD diffractometer	2169 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −4→5
Tmin = 0.968, Tmax = 0.984	k = −19→19
6039 measured reflections	l = −18→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.0883P] where P = (Fo2 + 2Fc2)/3
2169 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.20 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
N1	1.1576 (4)	0.66232 (10)	0.15016 (9)	0.0630 (5)
O1	1.0131 (3)	0.60739 (8)	0.19660 (7)	0.0607 (4)
O2	0.4550 (3)	0.46825 (8)	0.12822 (8)	0.0746 (5)
O3	0.6627 (3)	0.50549 (7)	0.25802 (7)	0.0576 (4)
C1	0.9997 (5)	0.69977 (13)	−0.07802 (12)	0.0712 (6)
H1	0.8549	0.6615	−0.0930	0.085*
C2	1.0757 (6)	0.75230 (15)	−0.13884 (14)	0.0828 (7)
H2	0.9802	0.7496	−0.1944	0.099*
C3	1.2896 (6)	0.80792 (14)	−0.11749 (17)	0.0844 (7)
H3	1.3391	0.8433	−0.1584	0.101*
C4	1.4315 (5)	0.81193 (13)	−0.03635 (16)	0.0845 (7)
H4	1.5793	0.8496	−0.0222	0.101*
C5	1.3566 (5)	0.76046 (12)	0.02457 (14)	0.0681 (6)
H5	1.4541	0.7636	0.0799	0.082*
C6	1.1380 (4)	0.70408 (10)	0.00457 (11)	0.0521 (5)
C7	1.0454 (4)	0.65230 (10)	0.07063 (10)	0.0491 (4)
C8	0.8306 (4)	0.59153 (11)	0.06221 (10)	0.0530 (5)
H8	0.7213	0.5728	0.0124	0.064*
C9	0.8187 (4)	0.56698 (10)	0.14107 (10)	0.0492 (5)
C10	0.6272 (4)	0.50799 (11)	0.17418 (11)	0.0525 (5)
C11	0.4715 (5)	0.45151 (12)	0.29747 (12)	0.0629 (5)
H11	0.2788	0.4501	0.2627	0.075*
C12	0.4454 (7)	0.48786 (17)	0.38172 (15)	0.1041 (10)
H12A	0.6342	0.4896	0.4158	0.156*
H12B	0.3159	0.4558	0.4099	0.156*
H12C	0.3692	0.5416	0.3738	0.156*
C13	0.6001 (6)	0.36909 (14)	0.30211 (16)	0.0981 (8)
H13A	0.6165	0.3505	0.2458	0.147*
H13B	0.4765	0.3331	0.3280	0.147*
H13C	0.7901	0.3705	0.3355	0.147*

	U11	U22	U33	U12	U13	U23
N1	0.0788 (12)	0.0650 (10)	0.0460 (9)	−0.0149 (9)	0.0112 (8)	0.0018 (7)
O1	0.0757 (9)	0.0651 (8)	0.0408 (7)	−0.0141 (7)	0.0070 (6)	0.0003 (6)
O2	0.0940 (11)	0.0756 (9)	0.0512 (8)	−0.0266 (8)	0.0007 (8)	−0.0020 (7)
O3	0.0695 (9)	0.0626 (8)	0.0410 (7)	−0.0099 (7)	0.0085 (6)	0.0042 (6)
C1	0.0870 (16)	0.0752 (14)	0.0524 (12)	−0.0040 (12)	0.0136 (11)	0.0074 (11)
C2	0.1036 (19)	0.0902 (17)	0.0575 (13)	0.0099 (15)	0.0219 (13)	0.0172 (12)
C3	0.111 (2)	0.0674 (15)	0.0847 (18)	0.0077 (14)	0.0463 (16)	0.0227 (13)
C4	0.1026 (19)	0.0696 (15)	0.0871 (17)	−0.0156 (13)	0.0332 (15)	0.0076 (13)
C5	0.0797 (15)	0.0618 (12)	0.0650 (13)	−0.0042 (11)	0.0182 (11)	0.0010 (10)
C6	0.0606 (12)	0.0479 (10)	0.0505 (11)	0.0045 (9)	0.0171 (9)	0.0010 (8)
C7	0.0570 (11)	0.0483 (10)	0.0427 (10)	0.0027 (9)	0.0095 (8)	−0.0019 (8)
C8	0.0630 (12)	0.0541 (11)	0.0409 (10)	−0.0005 (9)	0.0043 (9)	−0.0014 (8)
C9	0.0592 (11)	0.0474 (10)	0.0402 (10)	0.0009 (9)	0.0047 (8)	−0.0036 (8)
C10	0.0662 (12)	0.0493 (10)	0.0417 (10)	0.0033 (9)	0.0068 (9)	0.0004 (8)
C11	0.0712 (13)	0.0637 (13)	0.0550 (11)	−0.0105 (10)	0.0132 (10)	0.0104 (9)
C12	0.147 (3)	0.107 (2)	0.0693 (16)	−0.0330 (18)	0.0530 (17)	−0.0100 (14)
C13	0.122 (2)	0.0687 (15)	0.107 (2)	0.0054 (15)	0.0270 (17)	0.0262 (14)

N1—C7	1.306 (2)	C5—H5	0.9300
N1—O1	1.4022 (18)	C6—C7	1.468 (2)
O1—C9	1.345 (2)	C7—C8	1.409 (2)
O2—C10	1.198 (2)	C8—C9	1.327 (2)
O3—C10	1.3197 (19)	C8—H8	0.9300
O3—C11	1.463 (2)	C9—C10	1.469 (3)
C1—C6	1.377 (3)	C11—C13	1.489 (3)
C1—C2	1.384 (3)	C11—C12	1.490 (3)
C1—H1	0.9300	C11—H11	0.9800
C2—C3	1.361 (3)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.362 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.373 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.381 (3)
C7—N1—O1	105.89 (14)	C7—C8—H8	127.6
C9—O1—N1	107.68 (12)	C8—C9—O1	110.58 (16)
C10—O3—C11	117.22 (15)	C8—C9—C10	130.77 (17)
C6—C1—C2	120.2 (2)	O1—C9—C10	118.60 (15)
C6—C1—H1	119.9	O2—C10—O3	124.97 (18)
C2—C1—H1	119.9	O2—C10—C9	122.10 (16)
C3—C2—C1	120.1 (2)	O3—C10—C9	112.92 (16)
C3—C2—H2	119.9	O3—C11—C13	108.73 (18)
C1—C2—H2	119.9	O3—C11—C12	105.69 (16)
C2—C3—C4	120.2 (2)	C13—C11—C12	114.28 (19)
C2—C3—H3	119.9	O3—C11—H11	109.3
C4—C3—H3	119.9	C13—C11—H11	109.3
C3—C4—C5	120.1 (2)	C12—C11—H11	109.3
C3—C4—H4	120.0	C11—C12—H12A	109.5
C5—C4—H4	120.0	C11—C12—H12B	109.5
C4—C5—C6	120.7 (2)	H12A—C12—H12B	109.5
C4—C5—H5	119.6	C11—C12—H12C	109.5
C6—C5—H5	119.6	H12A—C12—H12C	109.5
C1—C6—C5	118.61 (18)	H12B—C12—H12C	109.5
C1—C6—C7	120.53 (18)	C11—C13—H13A	109.5
C5—C6—C7	120.80 (17)	C11—C13—H13B	109.5
N1—C7—C8	111.06 (15)	H13A—C13—H13B	109.5
N1—C7—C6	120.10 (16)	C11—C13—H13C	109.5
C8—C7—C6	128.77 (16)	H13A—C13—H13C	109.5
C9—C8—C7	104.79 (16)	H13B—C13—H13C	109.5
C9—C8—H8	127.6
C7—N1—O1—C9	−0.11 (18)	N1—C7—C8—C9	0.9 (2)
C6—C1—C2—C3	0.7 (3)	C6—C7—C8—C9	−176.01 (17)
C1—C2—C3—C4	0.4 (4)	C7—C8—C9—O1	−0.9 (2)
C2—C3—C4—C5	−0.8 (4)	C7—C8—C9—C10	176.46 (18)
C3—C4—C5—C6	0.1 (3)	N1—O1—C9—C8	0.68 (19)
C2—C1—C6—C5	−1.4 (3)	N1—O1—C9—C10	−177.06 (15)
C2—C1—C6—C7	175.88 (18)	C11—O3—C10—O2	−1.7 (3)
C4—C5—C6—C1	0.9 (3)	C11—O3—C10—C9	176.98 (15)
C4—C5—C6—C7	−176.28 (18)	C8—C9—C10—O2	5.0 (3)
O1—N1—C7—C8	−0.5 (2)	O1—C9—C10—O2	−177.82 (17)
O1—N1—C7—C6	176.73 (14)	C8—C9—C10—O3	−173.73 (18)
C1—C6—C7—N1	−173.13 (18)	O1—C9—C10—O3	3.5 (2)
C5—C6—C7—N1	4.0 (3)	C10—O3—C11—C13	84.7 (2)
C1—C6—C7—C8	3.5 (3)	C10—O3—C11—C12	−152.16 (19)
C5—C6—C7—C8	−179.33 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.37	3.277 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.37	3.277 (2)	166

Symmetry code: (i) .