organic compounds
N,N-Dimethyl-3-phenylisoxazole-5-carboxamide
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, C12H12N2O2, synthesized by ammonolysis of 3-phenylisoxazole-5-carbonyl chloride in dichloromethane, the dihedral angle between the isoxazole ring and the phenyl ring is 14.05 (7)°. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of C—H⋯O hydrogen bonds, generating rings of graph-set motif R22(10).
CCDC reference: 975721
Related literature
For the biological activity of isoxazole derivatives, see: Lopes et al. (2011). For the synthesis and 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: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 975721
https://doi.org/10.1107/S1600536813033199/rz5100sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033199/rz5100Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033199/rz5100Isup3.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 dropped into the solution and stirred for 20 minutes in ice bath. The solvent was removed under reduced pressure and the mixture was used for the next step without further purification. Dimethylamine (20 mmol, 0.9 g) was added subsequently and the mixture stirred for 6 h at room temperature. The resulting residue was purified as a white solid (1.82 g, 84% yield). Recrystallization in dichloromethane gave fine colourless crystals suitable for X-ray study. All chemicals were purchased by Sigma Aldrich Germany.
All H atoms were placed in idealized positions and allowed to ride on the respective parent atom, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2 Ueq(C) or 1.5Ueq(C) for methyl H atoms.
Isoxazoles are reactants or intermediates in the synthesis of compounds that have attracted chemists, biologists and pharmacologists interest. Isoxazole derivatives have been used as semiconductors and corrosion inhibitors. They also show widespread biological activities, and are employed as anthelmintics, antiparasitic, herbicidal, pesticides, fungicide and antiviral drugs (Lopes et al., 2011).
In the molecule of the title compound (Fig. 1), the dihedral angle between the phenyl and the isoxazole rings is 14.05 (7)°, which is bigger than that of 7.37 (19)° observed in the related compound isopropyl 3-phenylisoxazole-5-carboxylate (Wang et al., 2013). The bond lengths within the isoxazole ring are in agreement with those reported for isopropyl 3-phenylisoxazole-5-carboxylate. In the crystal, centrosymmetrically related molecules are linked into dimers by C—H···O hydrogen bonds (Table 1), generating a ring of graph-set motif R22(10).
For the biological activity of isoxazole derivatives, see: Lopes et al. (2011). For the synthesis and structure of a related compound, see: Wang et al. (2013).
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: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. |
C12H12N2O2 | Z = 4 |
Mr = 216.24 | F(000) = 456 |
Monoclinic, P21/c | Dx = 1.287 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.596 (3) Å | θ = 2.4–25.1° |
b = 12.377 (6) Å | µ = 0.09 mm−1 |
c = 12.123 (6) Å | T = 296 K |
β = 102.964 (8)° | Block, colourless |
V = 1110.7 (9) Å3 | 0.36 × 0.25 × 0.13 mm |
Bruker APEXII CCD area detector diffractometer | 1977 independent reflections |
Radiation source: fine-focus sealed tube | 1373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
phi and ω scans | θmax = 25.1°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −5→9 |
Tmin = 0.970, Tmax = 0.989 | k = −14→14 |
5434 measured reflections | l = −14→14 |
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0624P)2 + 0.0693P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1977 reflections | Δρmax = 0.14 e Å−3 |
148 parameters | Δρmin = −0.17 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: 0.007 (2) |
C12H12N2O2 | V = 1110.7 (9) Å3 |
Mr = 216.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.596 (3) Å | µ = 0.09 mm−1 |
b = 12.377 (6) Å | T = 296 K |
c = 12.123 (6) Å | 0.36 × 0.25 × 0.13 mm |
β = 102.964 (8)° |
Bruker APEXII CCD area detector diffractometer | 1977 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 1373 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.989 | Rint = 0.032 |
5434 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.14 e Å−3 |
1977 reflections | Δρmin = −0.17 e Å−3 |
148 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 | 0.4029 (3) | 0.01587 (14) | 0.33843 (15) | 0.0628 (6) | |
O1 | 0.3706 (2) | 0.11427 (10) | 0.27668 (12) | 0.0616 (5) | |
O2 | 0.1335 (2) | 0.15233 (11) | −0.00766 (12) | 0.0643 (5) | |
C1 | 0.3700 (3) | −0.19723 (17) | 0.43043 (18) | 0.0575 (6) | |
H1 | 0.4227 | −0.1441 | 0.4815 | 0.069* | |
C2 | 0.3675 (3) | −0.30437 (19) | 0.4660 (2) | 0.0659 (7) | |
H2 | 0.4206 | −0.3224 | 0.5405 | 0.079* | |
C3 | 0.2870 (3) | −0.38412 (18) | 0.3915 (2) | 0.0654 (7) | |
H3 | 0.2847 | −0.4552 | 0.4160 | 0.078* | |
C4 | 0.2103 (3) | −0.35728 (18) | 0.2807 (2) | 0.0654 (7) | |
H4 | 0.1563 | −0.4108 | 0.2305 | 0.079* | |
C5 | 0.2126 (3) | −0.25108 (17) | 0.24309 (18) | 0.0538 (6) | |
H5 | 0.1606 | −0.2341 | 0.1681 | 0.065* | |
C6 | 0.2930 (3) | −0.16985 (15) | 0.31781 (16) | 0.0448 (5) | |
C7 | 0.2953 (3) | −0.05662 (15) | 0.27653 (16) | 0.0431 (5) | |
C8 | 0.1948 (3) | −0.00969 (15) | 0.17427 (16) | 0.0470 (5) | |
H8 | 0.1123 | −0.0440 | 0.1166 | 0.056* | |
C9 | 0.2449 (3) | 0.09524 (15) | 0.17905 (16) | 0.0440 (5) | |
C10 | 0.1868 (3) | 0.18267 (15) | 0.09211 (17) | 0.0460 (5) | |
N2 | 0.1934 (2) | 0.28752 (12) | 0.12311 (13) | 0.0493 (5) | |
C12 | 0.1405 (4) | 0.36960 (17) | 0.03430 (19) | 0.0701 (7) | |
H12A | 0.1469 | 0.3393 | −0.0376 | 0.105* | |
H12B | 0.2209 | 0.4303 | 0.0506 | 0.105* | |
H12C | 0.0192 | 0.3929 | 0.0319 | 0.105* | |
C13 | 0.2324 (3) | 0.32936 (17) | 0.23967 (17) | 0.0613 (6) | |
H13A | 0.2315 | 0.2708 | 0.2915 | 0.092* | |
H13B | 0.1421 | 0.3814 | 0.2472 | 0.092* | |
H13C | 0.3491 | 0.3632 | 0.2564 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0738 (13) | 0.0460 (10) | 0.0568 (12) | −0.0028 (9) | −0.0101 (10) | 0.0042 (8) |
O1 | 0.0719 (10) | 0.0442 (8) | 0.0564 (9) | −0.0073 (7) | −0.0118 (8) | −0.0004 (7) |
O2 | 0.0872 (12) | 0.0580 (9) | 0.0411 (9) | −0.0080 (8) | 0.0000 (8) | −0.0026 (7) |
C1 | 0.0584 (14) | 0.0616 (13) | 0.0488 (13) | −0.0027 (11) | 0.0040 (11) | 0.0037 (11) |
C2 | 0.0668 (15) | 0.0713 (16) | 0.0552 (14) | 0.0036 (12) | 0.0048 (12) | 0.0208 (12) |
C3 | 0.0724 (16) | 0.0536 (14) | 0.0705 (17) | 0.0020 (12) | 0.0169 (13) | 0.0148 (12) |
C4 | 0.0806 (17) | 0.0477 (13) | 0.0657 (16) | −0.0039 (11) | 0.0117 (13) | −0.0004 (11) |
C5 | 0.0626 (14) | 0.0483 (12) | 0.0475 (12) | 0.0016 (10) | 0.0060 (11) | 0.0026 (10) |
C6 | 0.0430 (11) | 0.0442 (11) | 0.0458 (11) | 0.0019 (9) | 0.0073 (9) | 0.0020 (9) |
C7 | 0.0422 (11) | 0.0431 (11) | 0.0421 (12) | 0.0000 (9) | 0.0052 (9) | −0.0049 (9) |
C8 | 0.0517 (12) | 0.0461 (12) | 0.0394 (11) | −0.0049 (9) | 0.0017 (10) | −0.0041 (9) |
C9 | 0.0457 (11) | 0.0465 (11) | 0.0368 (11) | −0.0007 (9) | 0.0031 (9) | −0.0055 (9) |
C10 | 0.0497 (12) | 0.0449 (11) | 0.0425 (12) | −0.0056 (9) | 0.0087 (10) | −0.0027 (9) |
N2 | 0.0597 (11) | 0.0432 (9) | 0.0425 (10) | −0.0016 (8) | 0.0060 (8) | 0.0020 (8) |
C12 | 0.0889 (18) | 0.0525 (13) | 0.0637 (16) | −0.0034 (12) | 0.0059 (14) | 0.0114 (11) |
C13 | 0.0781 (16) | 0.0486 (12) | 0.0551 (14) | −0.0018 (11) | 0.0107 (12) | −0.0078 (11) |
N1—C7 | 1.327 (2) | C6—C7 | 1.490 (3) |
N1—O1 | 1.422 (2) | C7—C8 | 1.425 (3) |
O1—C9 | 1.364 (2) | C8—C9 | 1.351 (3) |
O2—C10 | 1.244 (2) | C8—H8 | 0.9300 |
C1—C2 | 1.396 (3) | C9—C10 | 1.506 (3) |
C1—C6 | 1.401 (3) | C10—N2 | 1.349 (2) |
C1—H1 | 0.9300 | N2—C12 | 1.469 (2) |
C2—C3 | 1.384 (3) | N2—C13 | 1.471 (2) |
C2—H2 | 0.9300 | C12—H12A | 0.9600 |
C3—C4 | 1.380 (3) | C12—H12B | 0.9600 |
C3—H3 | 0.9300 | C12—H12C | 0.9600 |
C4—C5 | 1.393 (3) | C13—H13A | 0.9600 |
C4—H4 | 0.9300 | C13—H13B | 0.9600 |
C5—C6 | 1.399 (3) | C13—H13C | 0.9600 |
C5—H5 | 0.9300 | ||
C7—N1—O1 | 105.64 (16) | C9—C8—H8 | 127.4 |
C9—O1—N1 | 108.28 (14) | C7—C8—H8 | 127.4 |
C2—C1—C6 | 119.9 (2) | C8—C9—O1 | 109.81 (16) |
C2—C1—H1 | 120.0 | C8—C9—C10 | 128.71 (18) |
C6—C1—H1 | 120.0 | O1—C9—C10 | 121.42 (16) |
C3—C2—C1 | 120.7 (2) | O2—C10—N2 | 123.01 (18) |
C3—C2—H2 | 119.6 | O2—C10—C9 | 116.34 (17) |
C1—C2—H2 | 119.6 | N2—C10—C9 | 120.64 (17) |
C4—C3—C2 | 119.4 (2) | C10—N2—C12 | 118.31 (17) |
C4—C3—H3 | 120.3 | C10—N2—C13 | 126.38 (16) |
C2—C3—H3 | 120.3 | C12—N2—C13 | 115.05 (16) |
C3—C4—C5 | 120.8 (2) | N2—C12—H12A | 109.5 |
C3—C4—H4 | 119.6 | N2—C12—H12B | 109.5 |
C5—C4—H4 | 119.6 | H12A—C12—H12B | 109.5 |
C4—C5—C6 | 120.2 (2) | N2—C12—H12C | 109.5 |
C4—C5—H5 | 119.9 | H12A—C12—H12C | 109.5 |
C6—C5—H5 | 119.9 | H12B—C12—H12C | 109.5 |
C5—C6—C1 | 118.91 (18) | N2—C13—H13A | 109.5 |
C5—C6—C7 | 119.67 (18) | N2—C13—H13B | 109.5 |
C1—C6—C7 | 121.42 (18) | H13A—C13—H13B | 109.5 |
N1—C7—C8 | 110.98 (17) | N2—C13—H13C | 109.5 |
N1—C7—C6 | 119.88 (17) | H13A—C13—H13C | 109.5 |
C8—C7—C6 | 129.14 (17) | H13B—C13—H13C | 109.5 |
C9—C8—C7 | 105.29 (17) | ||
C7—N1—O1—C9 | −0.6 (2) | N1—C7—C8—C9 | −1.2 (2) |
C6—C1—C2—C3 | −1.1 (3) | C6—C7—C8—C9 | 179.07 (19) |
C1—C2—C3—C4 | 0.7 (4) | C7—C8—C9—O1 | 0.8 (2) |
C2—C3—C4—C5 | −0.1 (4) | C7—C8—C9—C10 | 177.71 (19) |
C3—C4—C5—C6 | −0.1 (3) | N1—O1—C9—C8 | −0.1 (2) |
C4—C5—C6—C1 | −0.2 (3) | N1—O1—C9—C10 | −177.31 (16) |
C4—C5—C6—C7 | 179.77 (19) | C8—C9—C10—O2 | −24.5 (3) |
C2—C1—C6—C5 | 0.8 (3) | O1—C9—C10—O2 | 152.16 (19) |
C2—C1—C6—C7 | −179.19 (19) | C8—C9—C10—N2 | 155.4 (2) |
O1—N1—C7—C8 | 1.1 (2) | O1—C9—C10—N2 | −27.9 (3) |
O1—N1—C7—C6 | −179.12 (15) | O2—C10—N2—C12 | −2.0 (3) |
C5—C6—C7—N1 | −165.58 (19) | C9—C10—N2—C12 | 178.11 (18) |
C1—C6—C7—N1 | 14.4 (3) | O2—C10—N2—C13 | 171.7 (2) |
C5—C6—C7—C8 | 14.1 (3) | C9—C10—N2—C13 | −8.2 (3) |
C1—C6—C7—C8 | −165.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.43 | 3.340 (3) | 165 |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.43 | 3.340 (3) | 165 |
Symmetry code: (i) −x, −y, −z. |
Acknowledgements
Part of this work was supported by the Scientific Reserch Project of Xi'an Medical College (No. 10FC07) and the Scientific Reserch Project of the Affiliated Hospital of Xi'an Medical College (No. XYFY10–11).
References
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lopes, S., Nunes, C. M., Gómez-Zavaglia, A., Pinho e Melo, T. M. V. D. & Fausto, R. (2011). J. Phys. Chem. A, 115, 1199–1209. Google Scholar
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Wang, L., Liu, X.-Y., Li, Z.-W. & Zhang, S.-Y. (2013). Acta Cryst. E69, o733. CSD CrossRef IUCr Journals Google Scholar
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Isoxazoles are reactants or intermediates in the synthesis of compounds that have attracted chemists, biologists and pharmacologists interest. Isoxazole derivatives have been used as semiconductors and corrosion inhibitors. They also show widespread biological activities, and are employed as anthelmintics, antiparasitic, herbicidal, pesticides, fungicide and antiviral drugs (Lopes et al., 2011).
In the molecule of the title compound (Fig. 1), the dihedral angle between the phenyl and the isoxazole rings is 14.05 (7)°, which is bigger than that of 7.37 (19)° observed in the related compound isopropyl 3-phenylisoxazole-5-carboxylate (Wang et al., 2013). The bond lengths within the isoxazole ring are in agreement with those reported for isopropyl 3-phenylisoxazole-5-carboxylate. In the crystal, centrosymmetrically related molecules are linked into dimers by C—H···O hydrogen bonds (Table 1), generating a ring of graph-set motif R22(10).