3-(4-Meth-oxy-phen-yl)-5-methylisoxazole-4-carb-oxy-lic acid.

In the title compound, C12H11NO4, the dihedral angle between the benzene and isoxazole rings is 42.52 (8)°. The carb-oxy-lic acid group is close to being coplanar with the isoxazole ring [dihedral angle = 5.3 (2)°]. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R2(2)(8) loops.

Related literature

For the biological and pharmaceutical properties of isoxazoles, see: Changtam et al. (2010 ▶); Eddington et al. (2002 ▶); Kozikowski et al. (2008 ▶); Lee et al. (2009 ▶); Panda et al. (2009 ▶); Shin et al. (2005 ▶). For the agrochemical importance of isoxazoles, see: Pinho e Melo (2005 ▶7). For a related structure, see: Wolf et al. (1995 ▶).

Experimental

Crystal data

C12H11NO4

M = 233.22

Monoclinic,

a = 6.4147 (2) Å

b = 14.6321 (6) Å

c = 11.9911 (5) Å

β = 97.220 (2)°

V = 1116.57 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.979, T max = 0.989

11200 measured reflections

2811 independent reflections

2083 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.04

2811 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 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/S1600536813004029/hb7037sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004029/hb7037Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004029/hb7037Isup3.cml

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

C12H11NO4	F(000) = 488
Mr = 233.22	Dx = 1.387 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2811 reflections
a = 6.4147 (2) Å	θ = 2.2–28.5°
b = 14.6321 (6) Å	µ = 0.11 mm−1
c = 11.9911 (5) Å	T = 296 K
β = 97.220 (2)°	Block, yellow
V = 1116.57 (7) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	2083 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 28.5°, θmin = 2.2°
Tmin = 0.979, Tmax = 0.989	h = −8→8
11200 measured reflections	k = −19→19
2811 independent reflections	l = −16→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.2571P] where P = (Fo2 + 2Fc2)/3
2811 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 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
O2	0.2009 (2)	0.37793 (11)	0.57223 (11)	0.0848 (6)
O11	−0.25133 (16)	0.31776 (8)	−0.04335 (11)	0.0656 (4)
O16	0.35249 (16)	0.46156 (8)	0.09298 (9)	0.0573 (3)
O17	0.30828 (17)	0.44090 (8)	−0.09213 (9)	0.0639 (4)
N10	−0.2230 (2)	0.31499 (10)	0.07570 (13)	0.0649 (5)
C1	0.4132 (4)	0.37406 (19)	0.62109 (19)	0.0930 (9)
C3	0.1563 (3)	0.37111 (12)	0.45858 (15)	0.0627 (6)
C4	0.2992 (3)	0.34453 (12)	0.38735 (15)	0.0632 (6)
C5	0.2364 (2)	0.33990 (11)	0.27343 (15)	0.0595 (5)
C6	0.0325 (2)	0.36064 (9)	0.22778 (14)	0.0530 (5)
C7	−0.1095 (3)	0.38676 (11)	0.30087 (16)	0.0610 (6)
C8	−0.0479 (3)	0.39210 (13)	0.41410 (17)	0.0673 (6)
C9	−0.0393 (2)	0.35217 (9)	0.10713 (14)	0.0522 (5)
C12	−0.0825 (2)	0.35580 (9)	−0.07996 (14)	0.0534 (5)
C13	−0.0912 (3)	0.36697 (12)	−0.20259 (15)	0.0668 (6)
C14	0.0574 (2)	0.37919 (9)	0.01037 (13)	0.0482 (4)
C15	0.2528 (2)	0.42983 (9)	0.00688 (12)	0.0456 (4)
H1A	0.47240	0.31620	0.60400	0.1390*
H1B	0.42050	0.38080	0.70110	0.1390*
H1C	0.49070	0.42250	0.59130	0.1390*
H4	0.43650	0.32990	0.41620	0.0760*
H5	0.33320	0.32240	0.22590	0.0710*
H7	−0.24740	0.40070	0.27230	0.0730*
H8	−0.14420	0.41000	0.46170	0.0810*
H13A	−0.19650	0.32700	−0.23990	0.1000*
H13B	0.04310	0.35200	−0.22520	0.1000*
H13C	−0.12590	0.42910	−0.22260	0.1000*
H17	0.41870	0.46970	−0.08720	0.0960*

	U11	U22	U33	U12	U13	U23
O2	0.0740 (9)	0.1114 (11)	0.0710 (9)	0.0108 (8)	0.0169 (7)	0.0006 (7)
O11	0.0456 (6)	0.0581 (6)	0.0920 (9)	−0.0111 (5)	0.0041 (6)	−0.0073 (6)
O16	0.0490 (6)	0.0642 (6)	0.0598 (6)	−0.0145 (5)	0.0111 (5)	−0.0062 (5)
O17	0.0533 (6)	0.0795 (8)	0.0600 (7)	−0.0195 (5)	0.0115 (5)	−0.0047 (5)
N10	0.0499 (7)	0.0596 (8)	0.0863 (10)	−0.0112 (6)	0.0135 (7)	0.0006 (7)
C1	0.0791 (14)	0.1213 (19)	0.0774 (13)	0.0088 (13)	0.0054 (11)	0.0043 (12)
C3	0.0609 (10)	0.0593 (9)	0.0704 (11)	0.0010 (7)	0.0178 (8)	0.0052 (8)
C4	0.0501 (9)	0.0661 (10)	0.0749 (11)	0.0067 (7)	0.0133 (8)	0.0095 (8)
C5	0.0490 (8)	0.0571 (9)	0.0759 (11)	0.0060 (7)	0.0211 (7)	0.0057 (7)
C6	0.0474 (8)	0.0423 (7)	0.0716 (10)	−0.0025 (6)	0.0164 (7)	0.0062 (6)
C7	0.0448 (8)	0.0596 (9)	0.0810 (12)	0.0012 (6)	0.0177 (7)	0.0056 (8)
C8	0.0557 (9)	0.0705 (11)	0.0805 (12)	0.0050 (8)	0.0274 (8)	0.0019 (9)
C9	0.0408 (7)	0.0392 (7)	0.0783 (10)	−0.0009 (5)	0.0138 (7)	0.0021 (6)
C12	0.0421 (7)	0.0393 (7)	0.0786 (10)	−0.0005 (5)	0.0067 (7)	−0.0073 (6)
C13	0.0615 (10)	0.0635 (10)	0.0727 (11)	−0.0017 (8)	−0.0017 (8)	−0.0166 (8)
C14	0.0398 (7)	0.0375 (6)	0.0679 (9)	0.0006 (5)	0.0086 (6)	−0.0021 (6)
C15	0.0388 (7)	0.0410 (6)	0.0576 (8)	0.0012 (5)	0.0089 (6)	−0.0011 (6)

O2—C1	1.414 (3)	C9—C14	1.438 (2)
O2—C3	1.361 (2)	C12—C14	1.361 (2)
O11—N10	1.417 (2)	C12—C13	1.474 (2)
O11—C12	1.3397 (17)	C14—C15	1.4612 (18)
O16—C15	1.2347 (18)	C1—H1A	0.9600
O17—C15	1.2918 (18)	C1—H1B	0.9600
O17—H17	0.8200	C1—H1C	0.9600
N10—C9	1.3096 (19)	C4—H4	0.9300
C3—C4	1.385 (3)	C5—H5	0.9300
C3—C8	1.385 (3)	C7—H7	0.9300
C4—C5	1.376 (3)	C8—H8	0.9300
C5—C6	1.387 (2)	C13—H13A	0.9600
C6—C9	1.467 (2)	C13—H13B	0.9600
C6—C7	1.395 (2)	C13—H13C	0.9600
C7—C8	1.368 (3)
C1—O2—C3	118.84 (16)	O16—C15—C14	121.52 (13)
N10—O11—C12	109.60 (12)	O17—C15—C14	115.23 (13)
C15—O17—H17	109.00	O16—C15—O17	123.22 (13)
O11—N10—C9	105.96 (13)	O2—C1—H1A	109.00
O2—C3—C8	116.04 (17)	O2—C1—H1B	109.00
C4—C3—C8	119.47 (17)	O2—C1—H1C	109.00
O2—C3—C4	124.49 (17)	H1A—C1—H1B	109.00
C3—C4—C5	119.48 (17)	H1A—C1—H1C	110.00
C4—C5—C6	121.66 (15)	H1B—C1—H1C	109.00
C5—C6—C7	118.04 (16)	C3—C4—H4	120.00
C5—C6—C9	122.30 (13)	C5—C4—H4	120.00
C7—C6—C9	119.60 (13)	C4—C5—H5	119.00
C6—C7—C8	120.63 (17)	C6—C5—H5	119.00
C3—C8—C7	120.71 (18)	C6—C7—H7	120.00
N10—C9—C6	118.58 (14)	C8—C7—H7	120.00
N10—C9—C14	110.23 (14)	C3—C8—H8	120.00
C6—C9—C14	131.18 (12)	C7—C8—H8	120.00
O11—C12—C13	116.25 (14)	C12—C13—H13A	109.00
O11—C12—C14	108.85 (14)	C12—C13—H13B	109.00
C13—C12—C14	134.83 (14)	C12—C13—H13C	109.00
C9—C14—C15	128.39 (13)	H13A—C13—H13B	109.00
C12—C14—C15	125.95 (14)	H13A—C13—H13C	109.00
C9—C14—C12	105.36 (12)	H13B—C13—H13C	109.00
C1—O2—C3—C4	12.0 (3)	C7—C6—C9—C14	138.29 (16)
C1—O2—C3—C8	−168.49 (19)	C5—C6—C7—C8	0.4 (2)
C12—O11—N10—C9	0.60 (16)	C9—C6—C7—C8	177.77 (15)
N10—O11—C12—C13	−177.70 (13)	C6—C7—C8—C3	−0.4 (3)
N10—O11—C12—C14	−0.41 (15)	N10—C9—C14—C12	0.32 (16)
O11—N10—C9—C14	−0.55 (16)	N10—C9—C14—C15	174.29 (13)
O11—N10—C9—C6	178.83 (11)	C6—C9—C14—C12	−178.95 (14)
O2—C3—C8—C7	−179.51 (17)	C6—C9—C14—C15	−5.0 (2)
C4—C3—C8—C7	0.1 (3)	O11—C12—C14—C9	0.07 (14)
C8—C3—C4—C5	0.4 (3)	O11—C12—C14—C15	−174.09 (12)
O2—C3—C4—C5	179.90 (17)	C13—C12—C14—C9	176.64 (16)
C3—C4—C5—C6	−0.4 (3)	C13—C12—C14—C15	2.5 (3)
C4—C5—C6—C9	−177.26 (14)	C9—C14—C15—O16	−5.3 (2)
C4—C5—C6—C7	0.1 (2)	C9—C14—C15—O17	176.71 (13)
C5—C6—C9—N10	136.35 (15)	C12—C14—C15—O16	167.52 (14)
C5—C6—C9—C14	−44.4 (2)	C12—C14—C15—O17	−10.5 (2)
C7—C6—C9—N10	−40.94 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H17···O16i	0.82	1.79	2.6034 (16)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O17—H17⋯O16i	0.82	1.79	2.6034 (16)	173

Symmetry code: (i) .