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In the title compound, C12H11NO2, synthesized by 1,3-dipolar cyclo­addition reaction of nitrile oxides with sodium pentane-2,4-dionate, all bond lengths and angles are normal. In the mol­ecule, the isoxazole and phenyl rings make a dihedral angle of 84.8 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024415/cv2244sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024415/cv2244Isup2.hkl
Contains datablock I

CCDC reference: 651509

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.061
  • wR factor = 0.257
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C6
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.257 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Isoxazole derivatives exhibit anticonvulsant, antibacterial, antiasthmatic, and other pharmacological activities (Lin et al., 1997). Isoxazoles are typically prepared by the reaction of nitrile oxides with alkynes (Hanson & Mohamed, 1997) or olefine. In addition they are synthesized by cyclization of the adducts of alpha, beta-unsaturated ketones (or aldehydes) and hydroxylamines (Martins et al., 2000). In this article, we report here the crystal structure of 1-(5-methyl-3-phenyl-isoxazol -4-yl)ethanone synthesized by 1,3-Dipolar Cycloaddition reaction of nitrile oxideswith sodioacetylacetone (Doyle et al., 1963).

Related literature top

The synthesis of 1-(5-methyl-3-phenyl-isoxazol-4-yl)ethanone was described by Doyle et al. (1963); for the crystal structures of related complexes see Higgins et al. (1997).

For related literature, see: Hanson & Mohamed (1997); Lin et al. (1997); Martins et al. (2000).

Experimental top

A solution of alpha-chlorobenzaldoxime(0.02 mol) in methanol was added slowly to a stirred solution of sodioacetylacetone(0.026 mol) at 268–273 K in ice-salt bath. The mixture was stirred for 2 h and allowed to warm to room temperature, then kept on stirring for 2 h. After finished the reaction, the residue was shaken with water(200 ml), filtrated. The solid was crystallized from ethanol and water to give colorless prism crystals (yield 63.8%). M.p. 336 k. Analysis, found (calculated for C12H11NO2): C 71.63 (71.61%) H 5.51(5.54%) N 6.96(6.94%). Crystals were grown from a solution of ethanol by slow evaporation.

Refinement top

All H atoms were geometrically fixed with C—H = 0.93–0.96 Å, and were treated as riding with Uiso(H) = 1.2–1.5Ueq(parent atom).

Structure description top

Isoxazole derivatives exhibit anticonvulsant, antibacterial, antiasthmatic, and other pharmacological activities (Lin et al., 1997). Isoxazoles are typically prepared by the reaction of nitrile oxides with alkynes (Hanson & Mohamed, 1997) or olefine. In addition they are synthesized by cyclization of the adducts of alpha, beta-unsaturated ketones (or aldehydes) and hydroxylamines (Martins et al., 2000). In this article, we report here the crystal structure of 1-(5-methyl-3-phenyl-isoxazol -4-yl)ethanone synthesized by 1,3-Dipolar Cycloaddition reaction of nitrile oxideswith sodioacetylacetone (Doyle et al., 1963).

The synthesis of 1-(5-methyl-3-phenyl-isoxazol-4-yl)ethanone was described by Doyle et al. (1963); for the crystal structures of related complexes see Higgins et al. (1997).

For related literature, see: Hanson & Mohamed (1997); Lin et al. (1997); Martins et al. (2000).

Computing details top

Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the molecule structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The packing structure of the title compound viewed down the a axis.
1-(5-methyl-3-phenylisoxazol-4-yl)ethanone top
Crystal data top
C12H11NO2F(000) = 424
Mr = 201.22Dx = 1.266 Mg m3
Monoclinic, P21/nMelting point: 336 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 14.090 (3) ÅCell parameters from 5329 reflections
b = 5.2504 (11) Åθ = 3.3–27.5°
c = 14.280 (3) ŵ = 0.09 mm1
β = 92.60 (3)°T = 293 K
V = 1055.3 (4) Å3Prism, colourless
Z = 40.70 × 0.50 × 0.20 mm
Data collection top
Rigaku R-AXIS SPIDER
diffractometer
2410 independent reflections
Radiation source: Rotating Anode1444 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω oscillation scansθmax = 27.5°, θmin = 4.0°
Absorption correction: multi-scan
Higashi (1995)
h = 1818
Tmin = 0.942, Tmax = 0.983k = 66
10361 measured reflectionsl = 1818
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.15P)2 + 0.2275P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.061(Δ/σ)max < 0.001
wR(F2) = 0.257Δρmax = 0.24 e Å3
S = 1.05Δρmin = 0.22 e Å3
2410 reflectionsExtinction correction: SHELXL
137 parametersExtinction coefficient: 0.063 (14)
0 restraints
Crystal data top
C12H11NO2V = 1055.3 (4) Å3
Mr = 201.22Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.090 (3) ŵ = 0.09 mm1
b = 5.2504 (11) ÅT = 293 K
c = 14.280 (3) Å0.70 × 0.50 × 0.20 mm
β = 92.60 (3)°
Data collection top
Rigaku R-AXIS SPIDER
diffractometer
2410 independent reflections
Absorption correction: multi-scan
Higashi (1995)
1444 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.983Rint = 0.025
10361 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.257H-atom parameters constrained
S = 1.05Δρmax = 0.24 e Å3
2410 reflectionsΔρmin = 0.22 e Å3
137 parameters
Special details top

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
O10.25512 (14)0.1587 (4)0.82721 (12)0.0768 (6)
O20.46364 (16)0.6933 (5)0.89829 (16)0.0964 (8)
N10.19230 (16)0.2155 (5)0.89941 (16)0.0764 (7)
C10.1178 (3)0.6683 (8)1.0260 (2)0.1056 (12)
H10.10110.73830.96780.127*
C20.0734 (3)0.7530 (11)1.1046 (3)0.1268 (16)
H20.02860.88281.09890.152*
C30.0946 (3)0.6488 (8)1.1894 (2)0.0954 (11)
H30.06260.70041.24170.114*
C40.1624 (4)0.4698 (8)1.1971 (2)0.1256 (16)
H40.17930.40151.25560.151*
C50.2073 (4)0.3863 (7)1.1188 (2)0.1178 (15)
H50.25350.26021.12500.141*
C60.18481 (17)0.4861 (5)1.03262 (16)0.0601 (6)
C70.23385 (16)0.3934 (5)0.94913 (15)0.0572 (6)
C80.32306 (15)0.4644 (4)0.91255 (14)0.0536 (6)
C90.39362 (17)0.6557 (5)0.94341 (16)0.0607 (6)
C100.3788 (2)0.8049 (6)1.0298 (2)0.0759 (8)
H10C0.43070.92161.04040.114*
H10B0.37590.69131.08230.114*
H10A0.32040.89841.02260.114*
C110.33123 (17)0.3083 (5)0.83683 (15)0.0596 (6)
C120.4041 (2)0.2697 (6)0.76707 (18)0.0747 (8)
H12C0.38310.14070.72320.112*
H12B0.46260.21710.79840.112*
H12A0.41410.42640.73420.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0791 (12)0.0874 (13)0.0643 (11)0.0131 (10)0.0068 (9)0.0224 (9)
O20.0895 (15)0.1154 (17)0.0872 (14)0.0362 (12)0.0347 (12)0.0201 (12)
N10.0676 (13)0.0920 (16)0.0700 (14)0.0163 (12)0.0102 (11)0.0163 (12)
C10.097 (2)0.149 (3)0.0723 (18)0.047 (2)0.0205 (16)0.013 (2)
C20.100 (3)0.185 (4)0.098 (3)0.049 (3)0.031 (2)0.010 (3)
C30.093 (2)0.114 (3)0.083 (2)0.023 (2)0.0432 (17)0.0238 (18)
C40.200 (5)0.117 (3)0.0626 (18)0.023 (3)0.041 (2)0.0083 (19)
C50.189 (4)0.109 (3)0.0579 (16)0.054 (3)0.031 (2)0.0109 (17)
C60.0593 (13)0.0657 (13)0.0562 (12)0.0088 (11)0.0110 (9)0.0029 (10)
C70.0600 (13)0.0618 (13)0.0495 (11)0.0031 (10)0.0014 (9)0.0015 (10)
C80.0594 (12)0.0574 (12)0.0443 (10)0.0003 (9)0.0039 (8)0.0016 (9)
C90.0608 (13)0.0638 (13)0.0580 (13)0.0030 (10)0.0079 (10)0.0016 (10)
C100.0687 (16)0.0788 (17)0.0808 (17)0.0105 (13)0.0092 (13)0.0204 (14)
C110.0646 (14)0.0658 (13)0.0481 (11)0.0042 (11)0.0014 (10)0.0008 (10)
C120.0772 (17)0.0907 (19)0.0568 (13)0.0156 (14)0.0102 (12)0.0067 (13)
Geometric parameters (Å, º) top
O1—C111.331 (3)C5—H50.9300
O1—N11.421 (3)C6—C71.487 (3)
O2—C91.219 (3)C7—C81.432 (3)
N1—C71.297 (3)C8—C111.366 (3)
C1—C61.344 (4)C8—C91.467 (3)
C1—C21.383 (5)C9—C101.484 (4)
C1—H10.9300C10—H10C0.9600
C2—C31.350 (6)C10—H10B0.9600
C2—H20.9300C10—H10A0.9600
C3—C41.341 (5)C11—C121.477 (3)
C3—H30.9300C12—H12C0.9600
C4—C51.381 (5)C12—H12B0.9600
C4—H40.9300C12—H12A0.9600
C5—C61.362 (4)
C11—O1—N1109.08 (17)C8—C7—C6130.9 (2)
C7—N1—O1105.53 (19)C11—C8—C7103.9 (2)
C6—C1—C2121.0 (3)C11—C8—C9124.6 (2)
C6—C1—H1119.5C7—C8—C9131.5 (2)
C2—C1—H1119.5O2—C9—C8120.4 (2)
C3—C2—C1120.5 (4)O2—C9—C10120.1 (2)
C3—C2—H2119.8C8—C9—C10119.5 (2)
C1—C2—H2119.8C9—C10—H10C109.5
C4—C3—C2119.1 (3)C9—C10—H10B109.5
C4—C3—H3120.5H10C—C10—H10B109.5
C2—C3—H3120.5C9—C10—H10A109.5
C3—C4—C5120.4 (4)H10C—C10—H10A109.5
C3—C4—H4119.8H10B—C10—H10A109.5
C5—C4—H4119.8O1—C11—C8109.8 (2)
C6—C5—C4120.9 (4)O1—C11—C12115.5 (2)
C6—C5—H5119.5C8—C11—C12134.6 (2)
C4—C5—H5119.5C11—C12—H12C109.5
C1—C6—C5118.1 (3)C11—C12—H12B109.5
C1—C6—C7121.8 (2)H12C—C12—H12B109.5
C5—C6—C7120.1 (3)C11—C12—H12A109.5
N1—C7—C8111.7 (2)H12C—C12—H12A109.5
N1—C7—C6117.4 (2)H12B—C12—H12A109.5
C11—O1—N1—C70.6 (3)N1—C7—C8—C110.9 (3)
C6—C1—C2—C31.9 (7)C6—C7—C8—C11178.0 (2)
C1—C2—C3—C42.9 (7)N1—C7—C8—C9179.0 (2)
C2—C3—C4—C52.5 (7)C6—C7—C8—C92.1 (4)
C3—C4—C5—C61.0 (8)C11—C8—C9—O23.5 (4)
C2—C1—C6—C50.4 (6)C7—C8—C9—O2176.3 (3)
C2—C1—C6—C7179.6 (4)C11—C8—C9—C10176.9 (2)
C4—C5—C6—C10.1 (7)C7—C8—C9—C103.3 (4)
C4—C5—C6—C7179.9 (4)N1—O1—C11—C80.1 (3)
O1—N1—C7—C80.9 (3)N1—O1—C11—C12179.3 (2)
O1—N1—C7—C6178.2 (2)C7—C8—C11—O10.4 (3)
C1—C6—C7—N185.0 (4)C9—C8—C11—O1179.4 (2)
C5—C6—C7—N195.1 (4)C7—C8—C11—C12178.6 (3)
C1—C6—C7—C896.2 (4)C9—C8—C11—C121.5 (4)
C5—C6—C7—C883.8 (4)

Experimental details

Crystal data
Chemical formulaC12H11NO2
Mr201.22
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)14.090 (3), 5.2504 (11), 14.280 (3)
β (°) 92.60 (3)
V3)1055.3 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.70 × 0.50 × 0.20
Data collection
DiffractometerRigaku R-AXIS SPIDER
Absorption correctionMulti-scan
Higashi (1995)
Tmin, Tmax0.942, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
10361, 2410, 1444
Rint0.025
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.257, 1.05
No. of reflections2410
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.22

Computer programs: RAPID-AUTO (Rigaku 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXL97.

 

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