organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 29 November 2013; accepted 8 December 2013; online 24 December 2013)

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).

Related literature

For the biological activity of isoxazole derivatives, see: Lopes et al. (2011[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.]). For the synthesis and structure of a related compound, see: Wang et al. (2013[Wang, L., Liu, X.-Y., Li, Z.-W. & Zhang, S.-Y. (2013). Acta Cryst. E69, o733.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O2

  • Mr = 216.24

  • Monoclinic, P 21 /c

  • a = 7.596 (3) Å

  • b = 12.377 (6) Å

  • c = 12.123 (6) Å

  • β = 102.964 (8)°

  • V = 1110.7 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.36 × 0.25 × 0.13 mm

Data collection
  • Bruker APEXII CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.989

  • 5434 measured reflections

  • 1977 independent reflections

  • 1373 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.128

  • S = 1.03

  • 1977 reflections

  • 148 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯O2i 0.93 2.43 3.340 (3) 165
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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).

Related literature top

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 top

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.

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
N,N-Dimethyl-3-phenylisoxazole-5-carboxamide top
Crystal data top
C12H12N2O2Z = 4
Mr = 216.24F(000) = 456
Monoclinic, P21/cDx = 1.287 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.596 (3) Åθ = 2.4–25.1°
b = 12.377 (6) ŵ = 0.09 mm1
c = 12.123 (6) ÅT = 296 K
β = 102.964 (8)°Block, colourless
V = 1110.7 (9) Å30.36 × 0.25 × 0.13 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
1977 independent reflections
Radiation source: fine-focus sealed tube1373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
phi and ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 59
Tmin = 0.970, Tmax = 0.989k = 1414
5434 measured reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-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 reflectionsΔρmax = 0.14 e Å3
148 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (2)
Crystal data top
C12H12N2O2V = 1110.7 (9) Å3
Mr = 216.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.596 (3) ŵ = 0.09 mm1
b = 12.377 (6) ÅT = 296 K
c = 12.123 (6) Å0.36 × 0.25 × 0.13 mm
β = 102.964 (8)°
Data collection top
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 = 0.989Rint = 0.032
5434 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.14 e Å3
1977 reflectionsΔρmin = 0.17 e Å3
148 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4029 (3)0.01587 (14)0.33843 (15)0.0628 (6)
O10.3706 (2)0.11427 (10)0.27668 (12)0.0616 (5)
O20.1335 (2)0.15233 (11)0.00766 (12)0.0643 (5)
C10.3700 (3)0.19723 (17)0.43043 (18)0.0575 (6)
H10.42270.14410.48150.069*
C20.3675 (3)0.30437 (19)0.4660 (2)0.0659 (7)
H20.42060.32240.54050.079*
C30.2870 (3)0.38412 (18)0.3915 (2)0.0654 (7)
H30.28470.45520.41600.078*
C40.2103 (3)0.35728 (18)0.2807 (2)0.0654 (7)
H40.15630.41080.23050.079*
C50.2126 (3)0.25108 (17)0.24309 (18)0.0538 (6)
H50.16060.23410.16810.065*
C60.2930 (3)0.16985 (15)0.31781 (16)0.0448 (5)
C70.2953 (3)0.05662 (15)0.27653 (16)0.0431 (5)
C80.1948 (3)0.00969 (15)0.17427 (16)0.0470 (5)
H80.11230.04400.11660.056*
C90.2449 (3)0.09524 (15)0.17905 (16)0.0440 (5)
C100.1868 (3)0.18267 (15)0.09211 (17)0.0460 (5)
N20.1934 (2)0.28752 (12)0.12311 (13)0.0493 (5)
C120.1405 (4)0.36960 (17)0.03430 (19)0.0701 (7)
H12A0.14690.33930.03760.105*
H12B0.22090.43030.05060.105*
H12C0.01920.39290.03190.105*
C130.2324 (3)0.32936 (17)0.23967 (17)0.0613 (6)
H13A0.23150.27080.29150.092*
H13B0.14210.38140.24720.092*
H13C0.34910.36320.25640.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0738 (13)0.0460 (10)0.0568 (12)0.0028 (9)0.0101 (10)0.0042 (8)
O10.0719 (10)0.0442 (8)0.0564 (9)0.0073 (7)0.0118 (8)0.0004 (7)
O20.0872 (12)0.0580 (9)0.0411 (9)0.0080 (8)0.0000 (8)0.0026 (7)
C10.0584 (14)0.0616 (13)0.0488 (13)0.0027 (11)0.0040 (11)0.0037 (11)
C20.0668 (15)0.0713 (16)0.0552 (14)0.0036 (12)0.0048 (12)0.0208 (12)
C30.0724 (16)0.0536 (14)0.0705 (17)0.0020 (12)0.0169 (13)0.0148 (12)
C40.0806 (17)0.0477 (13)0.0657 (16)0.0039 (11)0.0117 (13)0.0004 (11)
C50.0626 (14)0.0483 (12)0.0475 (12)0.0016 (10)0.0060 (11)0.0026 (10)
C60.0430 (11)0.0442 (11)0.0458 (11)0.0019 (9)0.0073 (9)0.0020 (9)
C70.0422 (11)0.0431 (11)0.0421 (12)0.0000 (9)0.0052 (9)0.0049 (9)
C80.0517 (12)0.0461 (12)0.0394 (11)0.0049 (9)0.0017 (10)0.0041 (9)
C90.0457 (11)0.0465 (11)0.0368 (11)0.0007 (9)0.0031 (9)0.0055 (9)
C100.0497 (12)0.0449 (11)0.0425 (12)0.0056 (9)0.0087 (10)0.0027 (9)
N20.0597 (11)0.0432 (9)0.0425 (10)0.0016 (8)0.0060 (8)0.0020 (8)
C120.0889 (18)0.0525 (13)0.0637 (16)0.0034 (12)0.0059 (14)0.0114 (11)
C130.0781 (16)0.0486 (12)0.0551 (14)0.0018 (11)0.0107 (12)0.0078 (11)
Geometric parameters (Å, º) top
N1—C71.327 (2)C6—C71.490 (3)
N1—O11.422 (2)C7—C81.425 (3)
O1—C91.364 (2)C8—C91.351 (3)
O2—C101.244 (2)C8—H80.9300
C1—C21.396 (3)C9—C101.506 (3)
C1—C61.401 (3)C10—N21.349 (2)
C1—H10.9300N2—C121.469 (2)
C2—C31.384 (3)N2—C131.471 (2)
C2—H20.9300C12—H12A0.9600
C3—C41.380 (3)C12—H12B0.9600
C3—H30.9300C12—H12C0.9600
C4—C51.393 (3)C13—H13A0.9600
C4—H40.9300C13—H13B0.9600
C5—C61.399 (3)C13—H13C0.9600
C5—H50.9300
C7—N1—O1105.64 (16)C9—C8—H8127.4
C9—O1—N1108.28 (14)C7—C8—H8127.4
C2—C1—C6119.9 (2)C8—C9—O1109.81 (16)
C2—C1—H1120.0C8—C9—C10128.71 (18)
C6—C1—H1120.0O1—C9—C10121.42 (16)
C3—C2—C1120.7 (2)O2—C10—N2123.01 (18)
C3—C2—H2119.6O2—C10—C9116.34 (17)
C1—C2—H2119.6N2—C10—C9120.64 (17)
C4—C3—C2119.4 (2)C10—N2—C12118.31 (17)
C4—C3—H3120.3C10—N2—C13126.38 (16)
C2—C3—H3120.3C12—N2—C13115.05 (16)
C3—C4—C5120.8 (2)N2—C12—H12A109.5
C3—C4—H4119.6N2—C12—H12B109.5
C5—C4—H4119.6H12A—C12—H12B109.5
C4—C5—C6120.2 (2)N2—C12—H12C109.5
C4—C5—H5119.9H12A—C12—H12C109.5
C6—C5—H5119.9H12B—C12—H12C109.5
C5—C6—C1118.91 (18)N2—C13—H13A109.5
C5—C6—C7119.67 (18)N2—C13—H13B109.5
C1—C6—C7121.42 (18)H13A—C13—H13B109.5
N1—C7—C8110.98 (17)N2—C13—H13C109.5
N1—C7—C6119.88 (17)H13A—C13—H13C109.5
C8—C7—C6129.14 (17)H13B—C13—H13C109.5
C9—C8—C7105.29 (17)
C7—N1—O1—C90.6 (2)N1—C7—C8—C91.2 (2)
C6—C1—C2—C31.1 (3)C6—C7—C8—C9179.07 (19)
C1—C2—C3—C40.7 (4)C7—C8—C9—O10.8 (2)
C2—C3—C4—C50.1 (4)C7—C8—C9—C10177.71 (19)
C3—C4—C5—C60.1 (3)N1—O1—C9—C80.1 (2)
C4—C5—C6—C10.2 (3)N1—O1—C9—C10177.31 (16)
C4—C5—C6—C7179.77 (19)C8—C9—C10—O224.5 (3)
C2—C1—C6—C50.8 (3)O1—C9—C10—O2152.16 (19)
C2—C1—C6—C7179.19 (19)C8—C9—C10—N2155.4 (2)
O1—N1—C7—C81.1 (2)O1—C9—C10—N227.9 (3)
O1—N1—C7—C6179.12 (15)O2—C10—N2—C122.0 (3)
C5—C6—C7—N1165.58 (19)C9—C10—N2—C12178.11 (18)
C1—C6—C7—N114.4 (3)O2—C10—N2—C13171.7 (2)
C5—C6—C7—C814.1 (3)C9—C10—N2—C138.2 (3)
C1—C6—C7—C8165.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O2i0.932.433.340 (3)165
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O2i0.932.433.340 (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

First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationLopes, S., Nunes, C. M., Gómez-Zavaglia, A., Pinho e Melo, T. M. V. D. & Fausto, R. (2011). J. Phys. Chem. A, 115, 1199–1209.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, L., Liu, X.-Y., Li, Z.-W. & Zhang, S.-Y. (2013). Acta Cryst. E69, o733.  CSD CrossRef IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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