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

In the title compound, C11H9NO3, the dihedral angle between the isoxazole and phenyl rings is 19.79 (12), while the ester group is inclined to the isoxazole group by 12.14 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers lying parallel to (010).

Related literature

For the biological activity of isoxazole derivatives, see: Musad et al. (2011 ▶). For the synthesis and the structure of a related compound, see: Wang et al. (2013 ▶).

Experimental

Crystal data

C11H9NO3

M = 203.19

Monoclinic,

a = 12.2275 (18) Å

b = 13.604 (2) Å

c = 5.8746 (9) Å

β = 97.011 (3)°

V = 969.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.36 × 0.25 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.964, T max = 0.987

4807 measured reflections

1718 independent reflections

1238 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.133

S = 1.13

1718 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 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: SHELXL97, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814000038/su2682sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000038/su2682Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000038/su2682Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H9NO3	Z = 4
Mr = 203.19	F(000) = 424
Monoclinic, P21/c	Dx = 1.392 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.2275 (18) Å	θ = 1.7–25.1°
b = 13.604 (2) Å	µ = 0.10 mm−1
c = 5.8746 (9) Å	T = 296 K
β = 97.011 (3)°	Plate, colourless
V = 969.9 (3) Å3	0.36 × 0.25 × 0.13 mm

Bruker APEXII CCD diffractometer	1718 independent reflections
Radiation source: fine-focus sealed tube	1238 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
phi and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→10
Tmin = 0.964, Tmax = 0.987	k = −15→16
4807 measured reflections	l = −6→7

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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0531P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
1718 reflections	Δρmax = 0.17 e Å−3
138 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (19)

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	0.58165 (16)	0.12445 (15)	0.1263 (4)	0.0548 (6)
O1	0.69685 (13)	0.12779 (12)	0.1714 (3)	0.0568 (5)
O2	0.91297 (15)	0.11346 (15)	0.3629 (3)	0.0734 (7)
O3	0.85964 (13)	0.14679 (13)	0.7065 (3)	0.0601 (5)
C1	0.3828 (2)	0.15075 (17)	0.5374 (4)	0.0497 (7)
H1	0.4298	0.1742	0.6620	0.060*
C2	0.2707 (2)	0.14652 (19)	0.5489 (5)	0.0581 (7)
H2	0.2426	0.1677	0.6807	0.070*
C3	0.2004 (2)	0.11121 (19)	0.3669 (5)	0.0593 (8)
H3	0.1249	0.1088	0.3746	0.071*
C4	0.2428 (2)	0.07947 (19)	0.1727 (5)	0.0585 (7)
H4	0.1956	0.0546	0.0501	0.070*
C5	0.35431 (19)	0.08422 (18)	0.1585 (4)	0.0495 (7)
H5	0.3820	0.0632	0.0261	0.059*
C6	0.42544 (18)	0.12036 (15)	0.3418 (4)	0.0419 (6)
C7	0.54474 (18)	0.12641 (15)	0.3261 (4)	0.0404 (6)
C9	0.72372 (19)	0.13278 (17)	0.4011 (4)	0.0447 (6)
C10	0.63299 (18)	0.13246 (16)	0.5065 (4)	0.0451 (6)
H10	0.6286	0.1355	0.6633	0.054*
C11	0.8426 (2)	0.13030 (18)	0.4824 (5)	0.0511 (7)
C12	0.9720 (2)	0.1372 (2)	0.8127 (5)	0.0722 (9)
H12A	1.0015	0.0755	0.7694	0.108*
H12B	0.9737	0.1397	0.9764	0.108*
H12C	1.0154	0.1900	0.7629	0.108*

	U11	U22	U33	U12	U13	U23
N1	0.0377 (12)	0.0773 (16)	0.0498 (14)	−0.0009 (10)	0.0068 (10)	−0.0028 (11)
O1	0.0444 (11)	0.0800 (13)	0.0475 (11)	−0.0009 (9)	0.0119 (8)	−0.0010 (9)
O2	0.0451 (11)	0.1176 (18)	0.0603 (13)	0.0086 (11)	0.0184 (9)	0.0003 (11)
O3	0.0400 (10)	0.0877 (14)	0.0523 (12)	0.0010 (9)	0.0044 (8)	−0.0068 (10)
C1	0.0448 (15)	0.0555 (16)	0.0492 (16)	−0.0026 (12)	0.0074 (12)	−0.0066 (12)
C2	0.0490 (17)	0.0677 (18)	0.0603 (18)	0.0044 (13)	0.0173 (13)	−0.0047 (14)
C3	0.0363 (14)	0.0689 (19)	0.073 (2)	0.0013 (13)	0.0078 (14)	0.0140 (15)
C4	0.0425 (16)	0.0702 (18)	0.0598 (19)	−0.0053 (13)	−0.0062 (13)	0.0057 (14)
C5	0.0455 (15)	0.0563 (15)	0.0466 (16)	0.0009 (12)	0.0054 (12)	−0.0007 (12)
C6	0.0406 (14)	0.0411 (13)	0.0438 (14)	0.0013 (10)	0.0039 (11)	0.0035 (11)
C7	0.0412 (14)	0.0371 (13)	0.0427 (14)	0.0005 (10)	0.0040 (11)	−0.0020 (11)
C9	0.0441 (15)	0.0497 (15)	0.0405 (14)	−0.0008 (11)	0.0057 (11)	0.0024 (11)
C10	0.0427 (14)	0.0525 (15)	0.0407 (14)	0.0043 (12)	0.0075 (11)	−0.0007 (11)
C11	0.0451 (16)	0.0565 (16)	0.0529 (17)	0.0014 (12)	0.0108 (13)	0.0010 (13)
C12	0.0457 (17)	0.104 (2)	0.0639 (19)	0.0039 (15)	−0.0067 (14)	−0.0015 (17)

N1—C7	1.308 (3)	C4—C5	1.378 (3)
N1—O1	1.402 (2)	C4—H4	0.9300
O1—C9	1.351 (3)	C5—C6	1.389 (3)
O2—C11	1.197 (3)	C5—H5	0.9300
O3—C11	1.326 (3)	C6—C7	1.475 (3)
O3—C12	1.443 (3)	C7—C10	1.420 (3)
C1—C6	1.382 (3)	C9—C10	1.335 (3)
C1—C2	1.382 (3)	C9—C11	1.474 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.374 (4)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.379 (4)	C12—H12C	0.9600
C3—H3	0.9300
C7—N1—O1	106.16 (18)	C5—C6—C7	120.1 (2)
C9—O1—N1	107.86 (17)	N1—C7—C10	110.9 (2)
C11—O3—C12	116.1 (2)	N1—C7—C6	120.5 (2)
C6—C1—C2	120.3 (2)	C10—C7—C6	128.6 (2)
C6—C1—H1	119.8	C10—C9—O1	110.4 (2)
C2—C1—H1	119.8	C10—C9—C11	133.8 (2)
C3—C2—C1	120.4 (3)	O1—C9—C11	115.6 (2)
C3—C2—H2	119.8	C9—C10—C7	104.6 (2)
C1—C2—H2	119.8	C9—C10—H10	127.7
C2—C3—C4	119.4 (2)	C7—C10—H10	127.7
C2—C3—H3	120.3	O2—C11—O3	125.2 (2)
C4—C3—H3	120.3	O2—C11—C9	124.4 (3)
C5—C4—C3	120.7 (2)	O3—C11—C9	110.3 (2)
C5—C4—H4	119.7	O3—C12—H12A	109.5
C3—C4—H4	119.7	O3—C12—H12B	109.5
C4—C5—C6	120.0 (2)	H12A—C12—H12B	109.5
C4—C5—H5	120.0	O3—C12—H12C	109.5
C6—C5—H5	120.0	H12A—C12—H12C	109.5
C1—C6—C5	119.1 (2)	H12B—C12—H12C	109.5
C1—C6—C7	120.8 (2)
C7—N1—O1—C9	−0.7 (3)	C5—C6—C7—C10	−159.5 (2)
C6—C1—C2—C3	0.6 (4)	N1—O1—C9—C10	0.2 (3)
C1—C2—C3—C4	0.3 (4)	N1—O1—C9—C11	176.1 (2)
C2—C3—C4—C5	−1.0 (4)	O1—C9—C10—C7	0.2 (3)
C3—C4—C5—C6	0.7 (4)	C11—C9—C10—C7	−174.6 (3)
C2—C1—C6—C5	−0.9 (3)	N1—C7—C10—C9	−0.7 (3)
C2—C1—C6—C7	178.8 (2)	C6—C7—C10—C9	177.9 (2)
C4—C5—C6—C1	0.3 (3)	C12—O3—C11—O2	−4.0 (4)
C4—C5—C6—C7	−179.4 (2)	C12—O3—C11—C9	174.4 (2)
O1—N1—C7—C10	0.8 (3)	C10—C9—C11—O2	166.0 (3)
O1—N1—C7—C6	−177.87 (18)	O1—C9—C11—O2	−8.7 (4)
C1—C6—C7—N1	−160.8 (2)	C10—C9—C11—O3	−12.4 (4)
C5—C6—C7—N1	18.9 (3)	O1—C9—C11—O3	172.9 (2)
C1—C6—C7—C10	20.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.58	3.512 (3)	175
C12—H12B···O2ii	0.96	2.50	3.412 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.58	3.512 (3)	175
C12—H12B⋯O2ii	0.96	2.50	3.412 (3)	159

Symmetry codes: (i) ; (ii) .