5-Methyl-3-phenyl-isoxazole-4-carb-oxy-lic acid.

In the title compound, C11H9NO3, the phenyl and isoxazole rings form a dihedral angle of 56.64 (8)°. The carb-oxy group is almost in the same plane as the isoxazole ring with a C-C-C-O torsion angle of -3.3 (2)°. In the crystal, pairs of O-H⋯O hydrogen bonds link the mol-ecules into head-to-head dimers. C-H⋯N hydrogen bonds and π-π stacking inter-actions between phenyl rings [centroid-centroid distance = 3.9614 (17)Å] link the dimers into a three-dimensional network.

Related literature

For the biological and pharmaceutical importance of isoxazoles, see: Basappa et al., (2003 ▶); Conti et al. (1998 ▶); Kang et al. (2000 ▶); Lee et al. (2009 ▶); Shin et al. (2005 ▶); Stevens & Albizati (1984 ▶). For bond-length and angle data in related structures, see: Wolf et al. (1995 ▶); Chandra et al., (2013 ▶).

Experimental

Crystal data

C11H9NO3

M = 203.19

Monoclinic,

a = 11.953 (4) Å

b = 5.981 (2) Å

c = 14.142 (5) Å

β = 105.548 (6)°

V = 974.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

8619 measured reflections

1712 independent reflections

1558 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.05

1712 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 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/S1600536813011410/bg2504sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011410/bg2504Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011410/bg2504Isup3.cml

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

C11H9NO3	F(000) = 424
Mr = 203.19	Dx = 1.386 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1712 reflections
a = 11.953 (4) Å	θ = 2.0–25.0°
b = 5.981 (2) Å	µ = 0.10 mm−1
c = 14.142 (5) Å	T = 273 K
β = 105.548 (6)°	Block, yellow
V = 974.0 (6) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	Rint = 0.026
ω and φ scans	θmax = 25.0°, θmin = 2.0°
8619 measured reflections	h = −14→14
1712 independent reflections	k = −7→7
1558 reflections with I > 2σ(I)	l = −16→16

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0647P)2 + 0.1799P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1712 reflections	Δρmax = 0.19 e Å−3
138 parameters	Δρmin = −0.14 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: 0.078 (6)

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	0.78858 (10)	0.77608 (19)	−0.16618 (8)	0.0644 (4)
O14	0.98209 (9)	0.19333 (19)	−0.09796 (8)	0.0626 (4)
O15	0.89662 (9)	0.16156 (18)	0.02382 (7)	0.0583 (4)
N8	0.72219 (12)	0.7544 (2)	−0.09692 (10)	0.0627 (5)
C1	0.70696 (13)	0.6540 (3)	0.10434 (12)	0.0577 (5)
C2	0.65298 (14)	0.6027 (3)	0.17680 (13)	0.0667 (6)
C3	0.59319 (14)	0.4050 (3)	0.17315 (12)	0.0646 (6)
C4	0.58949 (14)	0.2546 (3)	0.09855 (13)	0.0634 (5)
C5	0.64525 (13)	0.3017 (3)	0.02718 (11)	0.0556 (5)
C6	0.70323 (11)	0.5035 (2)	0.02904 (9)	0.0458 (4)
C7	0.75633 (11)	0.5675 (2)	−0.05041 (10)	0.0465 (4)
C10	0.85935 (12)	0.6006 (2)	−0.15866 (10)	0.0503 (4)
C11	0.93670 (14)	0.6030 (3)	−0.22477 (11)	0.0643 (6)
C12	0.84386 (10)	0.4605 (2)	−0.08704 (9)	0.0445 (4)
C13	0.90974 (11)	0.2583 (2)	−0.05073 (10)	0.0454 (4)
H1	0.74570	0.78940	0.10620	0.0690*
H2	0.65710	0.70230	0.22810	0.0800*
H3	0.55530	0.37280	0.22100	0.0780*
H4	0.54920	0.12080	0.09630	0.0760*
H5	0.64400	0.19820	−0.02220	0.0670*
H11A	0.91180	0.49090	−0.27460	0.0960*
H11B	1.01490	0.57240	−0.18750	0.0960*
H11C	0.93350	0.74740	−0.25510	0.0960*
H14	1.01490	0.07930	−0.07260	0.0940*

	U11	U22	U33	U12	U13	U23
O9	0.0729 (7)	0.0625 (7)	0.0640 (7)	0.0040 (5)	0.0289 (6)	0.0164 (5)
O14	0.0661 (7)	0.0664 (7)	0.0657 (7)	0.0140 (5)	0.0357 (5)	0.0054 (5)
O15	0.0618 (6)	0.0630 (7)	0.0569 (6)	0.0092 (5)	0.0275 (5)	0.0080 (5)
N8	0.0654 (8)	0.0622 (8)	0.0683 (8)	0.0096 (6)	0.0312 (7)	0.0138 (6)
C1	0.0544 (8)	0.0569 (9)	0.0676 (9)	−0.0019 (7)	0.0264 (7)	−0.0099 (7)
C2	0.0636 (9)	0.0795 (11)	0.0660 (10)	0.0025 (8)	0.0328 (8)	−0.0163 (8)
C3	0.0604 (9)	0.0801 (11)	0.0630 (9)	0.0064 (8)	0.0332 (7)	0.0068 (8)
C4	0.0634 (9)	0.0615 (9)	0.0722 (10)	−0.0058 (7)	0.0304 (8)	0.0056 (8)
C5	0.0597 (9)	0.0553 (9)	0.0559 (8)	−0.0029 (7)	0.0226 (7)	−0.0044 (7)
C6	0.0397 (7)	0.0511 (8)	0.0488 (7)	0.0059 (5)	0.0155 (5)	0.0022 (6)
C7	0.0442 (7)	0.0481 (7)	0.0483 (7)	−0.0006 (6)	0.0142 (6)	0.0001 (6)
C10	0.0513 (7)	0.0547 (8)	0.0459 (7)	−0.0069 (6)	0.0147 (6)	−0.0019 (6)
C11	0.0708 (10)	0.0761 (11)	0.0535 (9)	−0.0162 (8)	0.0297 (8)	−0.0023 (7)
C12	0.0430 (7)	0.0496 (7)	0.0425 (7)	−0.0052 (5)	0.0145 (5)	−0.0040 (5)
C13	0.0432 (7)	0.0510 (8)	0.0449 (7)	−0.0037 (5)	0.0169 (5)	−0.0059 (6)

O9—N8	1.4222 (19)	C7—C12	1.4363 (19)
O9—C10	1.3342 (18)	C10—C12	1.3649 (19)
O14—C13	1.2863 (18)	C10—C11	1.481 (2)
O15—C13	1.2488 (17)	C12—C13	1.4593 (18)
O14—H14	0.8200	C1—H1	0.9300
N8—C7	1.3057 (18)	C2—H2	0.9300
C1—C2	1.384 (2)	C3—H3	0.9300
C1—C6	1.386 (2)	C4—H4	0.9300
C2—C3	1.375 (3)	C5—H5	0.9300
C3—C4	1.378 (3)	C11—H11A	0.9600
C4—C5	1.380 (2)	C11—H11B	0.9600
C5—C6	1.389 (2)	C11—H11C	0.9600
C6—C7	1.4813 (19)
O9···C10i	3.268 (2)	C10···O15iii	3.345 (2)
O9···C11i	3.351 (2)	C10···C13iii	3.566 (2)
O14···O15ii	2.6252 (18)	C11···O14	2.999 (2)
O14···C11	2.999 (2)	C11···O9iv	3.351 (2)
O15···C11iii	3.316 (2)	C11···N8iv	3.427 (2)
O15···O14ii	2.6252 (18)	C11···O15iii	3.316 (2)
O15···C13ii	3.367 (2)	C12···C13iii	3.496 (2)
O15···C5	3.132 (2)	C13···O15ii	3.367 (2)
O15···C6	3.102 (2)	C13···C10iii	3.566 (2)
O15···C10iii	3.345 (2)	C13···C12iii	3.496 (2)
O9···H11Ai	2.6500	C13···H14ii	2.6600
O14···H11B	2.6800	H1···N8	2.8200
O14···H14ii	2.9000	H11A···O9iv	2.6500
O15···H11Biii	2.7700	H11A···N8iv	2.5100
O15···H14ii	1.8100	H11B···O14	2.6800
N8···C11i	3.427 (2)	H11B···O15iii	2.7700
N8···H1	2.8200	H14···O14ii	2.9000
N8···H11Ai	2.5100	H14···O15ii	1.8100
C5···O15	3.132 (2)	H14···C13ii	2.6600
C6···O15	3.102 (2)	H14···H14ii	2.3700
C10···O9iv	3.268 (2)
N8—O9—C10	109.41 (11)	O14—C13—C12	116.24 (12)
C13—O14—H14	109.00	O15—C13—C12	120.20 (12)
O9—N8—C7	105.56 (12)	O14—C13—O15	123.54 (12)
C2—C1—C6	119.97 (16)	C2—C1—H1	120.00
C1—C2—C3	120.23 (16)	C6—C1—H1	120.00
C2—C3—C4	119.98 (16)	C1—C2—H2	120.00
C3—C4—C5	120.28 (16)	C3—C2—H2	120.00
C4—C5—C6	120.02 (15)	C2—C3—H3	120.00
C1—C6—C7	118.88 (12)	C4—C3—H3	120.00
C5—C6—C7	121.56 (12)	C3—C4—H4	120.00
C1—C6—C5	119.49 (13)	C5—C4—H4	120.00
N8—C7—C6	117.63 (12)	C4—C5—H5	120.00
N8—C7—C12	111.06 (12)	C6—C5—H5	120.00
C6—C7—C12	131.31 (11)	C10—C11—H11A	109.00
O9—C10—C11	115.59 (12)	C10—C11—H11B	109.00
O9—C10—C12	109.44 (12)	C10—C11—H11C	110.00
C11—C10—C12	134.94 (13)	H11A—C11—H11B	110.00
C7—C12—C13	128.23 (11)	H11A—C11—H11C	109.00
C10—C12—C13	127.03 (12)	H11B—C11—H11C	109.00
C7—C12—C10	104.53 (11)
C10—O9—N8—C7	0.33 (15)	C1—C6—C7—C12	124.36 (16)
N8—O9—C10—C11	−178.39 (12)	C5—C6—C7—N8	122.44 (15)
N8—O9—C10—C12	−0.04 (15)	N8—C7—C12—C10	0.45 (16)
O9—N8—C7—C12	−0.47 (15)	N8—C7—C12—C13	175.43 (13)
O9—N8—C7—C6	178.53 (11)	C6—C7—C12—C10	−178.37 (14)
C2—C1—C6—C5	−0.1 (2)	C6—C7—C12—C13	−3.4 (2)
C6—C1—C2—C3	−1.6 (3)	O9—C10—C12—C7	−0.23 (15)
C2—C1—C6—C7	176.80 (14)	O9—C10—C12—C13	−175.28 (12)
C1—C2—C3—C4	1.7 (3)	C11—C10—C12—C7	177.67 (16)
C2—C3—C4—C5	−0.2 (3)	C11—C10—C12—C13	2.6 (3)
C3—C4—C5—C6	−1.5 (3)	C7—C12—C13—O14	178.55 (13)
C4—C5—C6—C7	−175.22 (14)	C7—C12—C13—O15	−3.3 (2)
C4—C5—C6—C1	1.6 (2)	C10—C12—C13—O14	−7.5 (2)
C1—C6—C7—N8	−54.40 (19)	C10—C12—C13—O15	170.61 (13)
C5—C6—C7—C12	−58.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O15ii	0.82	1.81	2.6252 (18)	172
C11—H11A···N8iv	0.96	2.51	3.427 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O14—H14⋯O15i	0.82	1.81	2.6252 (18)	172
C11—H11A⋯N8ii	0.96	2.51	3.427 (2)	159

Symmetry codes: (i) ; (ii) .