Ethyl 5-(4-amino-phen-yl)isoxazole-3-carboxyl-ate.

The asymmetric unit of the title compound, C(12)H(12)N(2)O(3), contains two mol-ecules in which the benzene and isoxazole rings are almost coplanar, the dihedral angles between their mean planes being 1.76 (9) and 5.85 (8)°. The two mol-ecules inter-act with each other via N-H⋯N and N-H⋯O hydrogen bonds, which link the mol-ecules into layers parallel to the ac plane. The layers stack in a parallel mode with an inter-layer distance of 3.36 (7) Å.

Related literature

For the synthesis and biological activity of soxazoles, see; Silva et al. (2002 ▶); Changtam et al. (2010 ▶); Patel et al. (2010 ▶); Barceló et al. (2007 ▶); Yamamoto et al. (2007 ▶); Mao et al. (2010 ▶). For their structure–activity relationships, see: Andrzejak et al. (2011 ▶); Becht et al. (2006 ▶); Veronese et al. (1997 ▶). For our research in this area, see: Qi et al. (2011 ▶).

Experimental

Crystal data

C12H12N2O3

M = 232.24

Triclinic,

a = 7.591 (2) Å

b = 11.303 (4) Å

c = 13.818 (4) Å

α = 88.155 (4)°

β = 87.008 (4)°

γ = 86.233 (4)°

V = 1181.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.15 × 0.09 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.986, T max = 0.992

4901 measured reflections

4074 independent reflections

2636 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 0.98

4074 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010653/bv2198sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010653/bv2198Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010653/bv2198Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812010653/bv2198Isup4.cml

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

C12H12N2O3	Z = 4
Mr = 232.24	F(000) = 488
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.591 (2) Å	Cell parameters from 1005 reflections
b = 11.303 (4) Å	θ = 3.0–24.5°
c = 13.818 (4) Å	µ = 0.10 mm−1
α = 88.155 (4)°	T = 293 K
β = 87.008 (4)°	Block, yellow
γ = 86.233 (4)°	0.15 × 0.09 × 0.08 mm
V = 1181.0 (6) Å3

Bruker SMART CCD area-detector diffractometer	4074 independent reflections
Radiation source: fine-focus sealed tube	2636 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→8
Tmin = 0.986, Tmax = 0.992	k = −12→13
4901 measured reflections	l = −14→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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0658P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
4074 reflections	Δρmax = 0.18 e Å−3
308 parameters	Δρmin = −0.20 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: 0.0095 (16)

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	0.5335 (2)	−0.04171 (15)	0.21800 (13)	0.0772 (6)
H1A	0.5476	−0.1051	0.1850	0.093*
H1B	0.4906	−0.0450	0.2768	0.093*
N2	0.8174 (2)	0.50932 (15)	−0.07787 (12)	0.0667 (5)
O1	0.7833 (2)	0.39375 (12)	−0.04673 (10)	0.0676 (4)
O2	0.85208 (17)	0.74084 (11)	−0.09551 (9)	0.0599 (4)
O3	0.7322 (2)	0.76842 (12)	0.05446 (10)	0.0754 (5)
C1	0.5794 (3)	0.06453 (17)	0.17699 (14)	0.0546 (5)
C2	0.6487 (3)	0.07114 (18)	0.08224 (14)	0.0588 (5)
H2B	0.6668	0.0021	0.0473	0.071*
C3	0.6913 (3)	0.17713 (17)	0.03879 (14)	0.0568 (5)
H3A	0.7380	0.1788	−0.0248	0.068*
C4	0.6653 (2)	0.28223 (16)	0.08896 (13)	0.0487 (5)
C5	0.5955 (3)	0.27542 (17)	0.18384 (14)	0.0559 (5)
H5A	0.5774	0.3444	0.2189	0.067*
C6	0.5525 (3)	0.16923 (18)	0.22717 (14)	0.0585 (5)
H6A	0.5050	0.1675	0.2906	0.070*
C7	0.7110 (2)	0.39554 (17)	0.04488 (13)	0.0483 (5)
C8	0.6983 (2)	0.50841 (17)	0.07360 (13)	0.0517 (5)
H8A	0.6549	0.5362	0.1334	0.062*
C9	0.7640 (2)	0.57479 (17)	−0.00509 (13)	0.0492 (5)
C10	0.7795 (3)	0.70477 (18)	−0.01060 (14)	0.0530 (5)
C11	0.8622 (3)	0.86764 (17)	−0.11021 (14)	0.0612 (6)
H11A	0.9401	0.8978	−0.0647	0.073*
H11B	0.7460	0.9077	−0.1005	0.073*
C12	0.9325 (3)	0.8886 (2)	−0.21169 (16)	0.0807 (7)
H12A	0.9406	0.9722	−0.2240	0.121*
H12B	0.8544	0.8583	−0.2560	0.121*
H12C	1.0477	0.8489	−0.2203	0.121*
N3	0.0413 (3)	0.56811 (15)	0.72204 (13)	0.0812 (6)
H3B	0.0532	0.6332	0.6891	0.097*
H3C	−0.0011	0.5699	0.7810	0.097*
N4	0.3229 (2)	0.01690 (15)	0.42390 (11)	0.0633 (5)
O4	0.2962 (2)	0.13256 (12)	0.45691 (9)	0.0659 (4)
O5	0.33623 (18)	−0.21554 (12)	0.40201 (9)	0.0609 (4)
O6	0.2162 (2)	−0.24455 (13)	0.55129 (10)	0.0821 (5)
C13	0.0896 (3)	0.46186 (17)	0.68074 (14)	0.0552 (5)
C14	0.1581 (3)	0.45657 (18)	0.58602 (14)	0.0600 (6)
H14A	0.1750	0.5268	0.5508	0.072*
C15	0.2013 (3)	0.35068 (17)	0.54298 (14)	0.0561 (5)
H15A	0.2459	0.3504	0.4790	0.067*
C16	0.1801 (2)	0.24361 (16)	0.59284 (13)	0.0480 (5)
C17	0.1131 (3)	0.24851 (17)	0.68872 (13)	0.0539 (5)
H17A	0.0984	0.1781	0.7240	0.065*
C18	0.0685 (3)	0.35428 (17)	0.73236 (13)	0.0554 (5)
H18A	0.0241	0.3548	0.7964	0.066*
C19	0.2207 (2)	0.13038 (16)	0.54784 (13)	0.0476 (5)
C20	0.1997 (3)	0.01638 (16)	0.57400 (13)	0.0538 (5)
H20A	0.1517	−0.0124	0.6327	0.065*
C21	0.2648 (2)	−0.04958 (16)	0.49515 (13)	0.0478 (5)
C22	0.2698 (3)	−0.18029 (18)	0.48701 (14)	0.0541 (5)
C23	0.3394 (3)	−0.34175 (17)	0.38527 (15)	0.0625 (6)
H23A	0.2214	−0.3695	0.3949	0.075*
H23B	0.4157	−0.3853	0.4301	0.075*
C24	0.4079 (3)	−0.3605 (2)	0.28296 (16)	0.0858 (8)
H24A	0.4114	−0.4435	0.2695	0.129*
H24B	0.5248	−0.3330	0.2744	0.129*
H24C	0.3314	−0.3171	0.2393	0.129*

	U11	U22	U33	U12	U13	U23
N1	0.1088 (16)	0.0514 (11)	0.0701 (12)	−0.0117 (10)	0.0120 (11)	0.0054 (9)
N2	0.0963 (14)	0.0488 (11)	0.0533 (10)	−0.0078 (9)	0.0149 (9)	0.0033 (8)
O1	0.0967 (12)	0.0534 (9)	0.0509 (8)	−0.0076 (7)	0.0199 (7)	−0.0033 (6)
O2	0.0678 (10)	0.0536 (9)	0.0568 (8)	−0.0068 (7)	0.0106 (7)	0.0064 (6)
O3	0.1151 (13)	0.0534 (9)	0.0553 (9)	−0.0011 (8)	0.0141 (9)	−0.0025 (7)
C1	0.0528 (13)	0.0533 (13)	0.0576 (12)	−0.0051 (9)	−0.0034 (10)	0.0033 (10)
C2	0.0649 (14)	0.0523 (13)	0.0592 (13)	−0.0035 (10)	0.0018 (10)	−0.0088 (10)
C3	0.0693 (15)	0.0539 (13)	0.0465 (11)	−0.0036 (10)	0.0044 (10)	−0.0044 (9)
C4	0.0496 (12)	0.0488 (12)	0.0472 (11)	−0.0020 (9)	−0.0003 (9)	−0.0007 (9)
C5	0.0620 (14)	0.0509 (12)	0.0542 (12)	−0.0048 (10)	0.0088 (10)	−0.0077 (9)
C6	0.0676 (14)	0.0577 (13)	0.0492 (11)	−0.0079 (10)	0.0102 (10)	−0.0008 (10)
C7	0.0473 (12)	0.0544 (13)	0.0423 (10)	−0.0010 (9)	0.0023 (8)	−0.0016 (9)
C8	0.0592 (13)	0.0518 (13)	0.0433 (11)	−0.0030 (9)	0.0069 (9)	−0.0031 (9)
C9	0.0488 (12)	0.0525 (12)	0.0456 (11)	−0.0009 (9)	0.0011 (9)	−0.0010 (9)
C10	0.0570 (13)	0.0518 (12)	0.0492 (12)	−0.0001 (9)	−0.0022 (10)	0.0050 (10)
C11	0.0560 (13)	0.0543 (13)	0.0723 (14)	−0.0050 (10)	0.0010 (11)	0.0117 (10)
C12	0.0848 (18)	0.0749 (16)	0.0781 (16)	−0.0020 (13)	0.0148 (13)	0.0259 (12)
N3	0.1247 (18)	0.0499 (12)	0.0672 (12)	−0.0007 (11)	0.0104 (11)	−0.0075 (9)
N4	0.0878 (13)	0.0491 (11)	0.0515 (10)	−0.0044 (9)	0.0132 (9)	−0.0037 (8)
O4	0.0948 (11)	0.0497 (9)	0.0510 (8)	−0.0054 (7)	0.0186 (7)	0.0013 (6)
O5	0.0722 (10)	0.0545 (9)	0.0560 (9)	−0.0103 (7)	0.0109 (7)	−0.0109 (6)
O6	0.1332 (15)	0.0530 (9)	0.0592 (9)	−0.0192 (9)	0.0197 (9)	−0.0005 (7)
C13	0.0627 (14)	0.0497 (12)	0.0533 (12)	−0.0020 (10)	−0.0045 (10)	−0.0040 (9)
C14	0.0734 (15)	0.0504 (13)	0.0558 (12)	−0.0088 (10)	0.0014 (11)	0.0075 (10)
C15	0.0680 (14)	0.0541 (13)	0.0452 (11)	−0.0061 (10)	0.0073 (10)	0.0032 (9)
C16	0.0503 (12)	0.0468 (12)	0.0462 (11)	−0.0025 (9)	0.0012 (9)	0.0002 (9)
C17	0.0649 (14)	0.0476 (12)	0.0482 (11)	−0.0036 (9)	0.0033 (10)	0.0058 (9)
C18	0.0657 (14)	0.0544 (13)	0.0450 (11)	−0.0012 (10)	0.0033 (9)	−0.0019 (9)
C19	0.0469 (12)	0.0542 (12)	0.0409 (10)	−0.0039 (9)	0.0028 (8)	0.0024 (9)
C20	0.0666 (14)	0.0495 (12)	0.0446 (11)	−0.0096 (10)	0.0093 (10)	0.0018 (9)
C21	0.0493 (12)	0.0505 (12)	0.0434 (11)	−0.0078 (9)	0.0028 (9)	0.0008 (9)
C22	0.0595 (13)	0.0561 (13)	0.0470 (12)	−0.0079 (10)	0.0026 (10)	−0.0062 (10)
C23	0.0619 (14)	0.0555 (14)	0.0712 (14)	−0.0097 (10)	0.0025 (11)	−0.0152 (10)
C24	0.0895 (19)	0.0888 (18)	0.0801 (17)	−0.0188 (14)	0.0221 (14)	−0.0357 (14)

N1—C1	1.369 (2)	N3—C13	1.366 (2)
N1—H1A	0.8600	N3—H3B	0.8600
N1—H1B	0.8600	N3—H3C	0.8600
N2—C9	1.300 (2)	N4—C21	1.296 (2)
N2—O1	1.398 (2)	N4—O4	1.397 (2)
O1—C7	1.354 (2)	O4—C19	1.354 (2)
O2—C10	1.333 (2)	O5—C22	1.317 (2)
O2—C11	1.448 (2)	O5—C23	1.451 (2)
O3—C10	1.195 (2)	O6—C22	1.201 (2)
C1—C2	1.387 (3)	C13—C14	1.384 (3)
C1—C6	1.389 (3)	C13—C18	1.404 (3)
C2—C3	1.373 (3)	C14—C15	1.367 (3)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.392 (3)	C15—C16	1.388 (3)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.390 (2)	C16—C17	1.396 (2)
C4—C7	1.455 (2)	C16—C19	1.449 (3)
C5—C6	1.375 (3)	C17—C18	1.371 (3)
C5—H5A	0.9300	C17—H17A	0.9300
C6—H6A	0.9300	C18—H18A	0.9300
C7—C8	1.344 (3)	C19—C20	1.344 (2)
C8—C9	1.391 (2)	C20—C21	1.391 (2)
C8—H8A	0.9300	C20—H20A	0.9300
C9—C10	1.481 (3)	C21—C22	1.483 (3)
C11—C12	1.491 (3)	C23—C24	1.497 (3)
C11—H11A	0.9700	C23—H23A	0.9700
C11—H11B	0.9700	C23—H23B	0.9700
C12—H12A	0.9600	C24—H24A	0.9600
C12—H12B	0.9600	C24—H24B	0.9600
C12—H12C	0.9600	C24—H24C	0.9600
C1—N1—H1A	120.0	C13—N3—H3B	120.0
C1—N1—H1B	120.0	C13—N3—H3C	120.0
H1A—N1—H1B	120.0	H3B—N3—H3C	120.0
C9—N2—O1	104.72 (15)	C21—N4—O4	104.79 (15)
C7—O1—N2	109.27 (14)	C19—O4—N4	109.59 (13)
C10—O2—C11	116.18 (15)	C22—O5—C23	116.53 (15)
N1—C1—C2	120.60 (18)	N3—C13—C14	121.13 (18)
N1—C1—C6	121.43 (19)	N3—C13—C18	121.11 (19)
C2—C1—C6	117.93 (18)	C14—C13—C18	117.75 (18)
C3—C2—C1	121.62 (18)	C15—C14—C13	121.60 (18)
C3—C2—H2B	119.2	C15—C14—H14A	119.2
C1—C2—H2B	119.2	C13—C14—H14A	119.2
C2—C3—C4	120.66 (18)	C14—C15—C16	121.32 (18)
C2—C3—H3A	119.7	C14—C15—H15A	119.3
C4—C3—H3A	119.7	C16—C15—H15A	119.3
C5—C4—C3	117.62 (17)	C15—C16—C17	117.28 (17)
C5—C4—C7	120.65 (16)	C15—C16—C19	122.22 (17)
C3—C4—C7	121.72 (17)	C17—C16—C19	120.48 (16)
C6—C5—C4	121.65 (18)	C18—C17—C16	121.82 (17)
C6—C5—H5A	119.2	C18—C17—H17A	119.1
C4—C5—H5A	119.2	C16—C17—H17A	119.1
C5—C6—C1	120.52 (19)	C17—C18—C13	120.22 (18)
C5—C6—H6A	119.7	C17—C18—H18A	119.9
C1—C6—H6A	119.7	C13—C18—H18A	119.9
C8—C7—O1	108.23 (16)	C20—C19—O4	107.67 (16)
C8—C7—C4	134.92 (17)	C20—C19—C16	135.29 (17)
O1—C7—C4	116.84 (16)	O4—C19—C16	117.04 (15)
C7—C8—C9	105.37 (17)	C19—C20—C21	105.79 (16)
C7—C8—H8A	127.3	C19—C20—H20A	127.1
C9—C8—H8A	127.3	C21—C20—H20A	127.1
N2—C9—C8	112.39 (18)	N4—C21—C20	112.16 (17)
N2—C9—C10	120.72 (17)	N4—C21—C22	120.80 (17)
C8—C9—C10	126.88 (18)	C20—C21—C22	127.03 (17)
O3—C10—O2	124.84 (19)	O6—C22—O5	125.0 (2)
O3—C10—C9	123.04 (18)	O6—C22—C21	122.62 (18)
O2—C10—C9	112.13 (17)	O5—C22—C21	112.33 (16)
O2—C11—C12	107.24 (16)	O5—C23—C24	107.44 (17)
O2—C11—H11A	110.3	O5—C23—H23A	110.2
C12—C11—H11A	110.3	C24—C23—H23A	110.2
O2—C11—H11B	110.3	O5—C23—H23B	110.2
C12—C11—H11B	110.3	C24—C23—H23B	110.2
H11A—C11—H11B	108.5	H23A—C23—H23B	108.5
C11—C12—H12A	109.5	C23—C24—H24A	109.5
C11—C12—H12B	109.5	C23—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
C11—C12—H12C	109.5	C23—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···N2i	0.86	2.44	3.243 (3)	157
N3—H3B···O6ii	0.86	2.62	3.396 (2)	150
N1—H1B···N4	0.86	2.44	3.255 (3)	159
N1—H1A···O3iii	0.86	2.63	3.394 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3C⋯N2i	0.86	2.44	3.243 (3)	157
N3—H3B⋯O6ii	0.86	2.62	3.396 (2)	150
N1—H1B⋯N4	0.86	2.44	3.255 (3)	159
N1—H1A⋯O3iii	0.86	2.63	3.394 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) .