organic compounds
Methyl 3-phenylisoxazole-5-carboxylate
aAffiliated Hospital of Xi'an Medical College, 48 Fenghao West Road, 710077, Xi'an, People's Republic of China
*Correspondence e-mail: liyajun9@hotmail.com
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, molecules are linked by C—H⋯O hydrogen bonds, forming layers lying parallel to (010).
CCDC reference: 979314
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
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Data collection: APEX2 (Bruker, 2008); cell 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).
Supporting information
CCDC reference: 979314
10.1107/S1600536814000038/su2682sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000038/su2682Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000038/su2682Isup3.cml
3-Phenylisoxazole-5-carboxylic acid (10 mmol, 1.95 g; Wang et al., 2013) was dissolved in 100 ml dichloromethane, then thionyl chloride (12 mmol, 1.43 g) was added drop wise while the solution was stirred for 20 minutes in an ice bath. The solvent was removed under reduced pressure and the mixture was used for the next step without further purification. Methanol (20 mmol, 0.64 g) was then added and the mixture stirred for 6 h at room temperature. The resulting residue was purified as a white solid (1.54 g; 76% yield). Recrystallization in dichloromethane gave fine colourless plate-like crystals suitable for X-ray diffraction analysis.
All H atoms were placed in idealized positions and allowed to ride on the respective parent atom: C—H = 0.93–0.96 Å with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
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) |
C11H9NO3 | V = 969.9 (3) Å3 |
Mr = 203.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2275 (18) Å | µ = 0.10 mm−1 |
b = 13.604 (2) Å | T = 296 K |
c = 5.8746 (9) Å | 0.36 × 0.25 × 0.13 mm |
β = 97.011 (3)° |
Bruker APEXII CCD diffractometer | 1718 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 1238 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.987 | Rint = 0.036 |
4807 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.17 e Å−3 |
1718 reflections | Δρmin = −0.15 e Å−3 |
138 parameters |
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 |
Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1. |
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) x−1, y, z; (ii) x, y, z+1. |
Acknowledgements
Part of this work was supported by the Basic Research Project of the Natural Science Foundation of Shaanxi Province (No. 2009JM4035) and the Project of the Health Office of Shaanxi Province (No. 08H38).
References
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The wide occurrence of heterocycles, such as isoxazoles, in bioactive natural products, pharmaceuticals and agrochemicals has made them important synthetic targets. They are of great importance in biological chemistry, showing anticancer activity, and substituted isoxazoles have revealed antibacterial, antioxidant, insecticidal properties (Musad et al., 2011). Here we report on the crystal structure of the title isoxazole derivative, synthesized by alcoholysis of 3-Phenyl-isoxazole-5-carbonyl chloride in dichloromethane.
In the molecule of the title compound, Fig. 1, the dihedral angle between the phenyl and the isoxazole rings is 19.79 (12) °. This is larger than that of 7.37 (19)° observed in the related compound Isopropyl 3-phenylisoxazole-5-carboxylate (Wang et al., 2013), but the bond lengths within the isoxazole ring are the same.
In the crystal, molecules are linked by C—H···O hydrogen bonds (Table 1), forming layers lying parallel to (010).