Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024415/cv2244sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024415/cv2244Isup2.hkl |
CCDC reference: 651509
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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).
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).
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.
C12H11NO2 | F(000) = 424 |
Mr = 201.22 | Dx = 1.266 Mg m−3 |
Monoclinic, P21/n | Melting point: 336 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 14.090 (3) Å | Cell parameters from 5329 reflections |
b = 5.2504 (11) Å | θ = 3.3–27.5° |
c = 14.280 (3) Å | µ = 0.09 mm−1 |
β = 92.60 (3)° | T = 293 K |
V = 1055.3 (4) Å3 | Prism, colourless |
Z = 4 | 0.70 × 0.50 × 0.20 mm |
Rigaku R-AXIS SPIDER diffractometer | 2410 independent reflections |
Radiation source: Rotating Anode | 1444 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω oscillation scans | θmax = 27.5°, θmin = 4.0° |
Absorption correction: multi-scan Higashi (1995) | h = −18→18 |
Tmin = 0.942, Tmax = 0.983 | k = −6→6 |
10361 measured reflections | l = −18→18 |
Refinement on F2 | H-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) = 0.257 | Δρmax = 0.24 e Å−3 |
S = 1.05 | Δρmin = −0.22 e Å−3 |
2410 reflections | Extinction correction: SHELXL |
137 parameters | Extinction coefficient: 0.063 (14) |
0 restraints |
C12H11NO2 | V = 1055.3 (4) Å3 |
Mr = 201.22 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.090 (3) Å | µ = 0.09 mm−1 |
b = 5.2504 (11) Å | T = 293 K |
c = 14.280 (3) Å | 0.70 × 0.50 × 0.20 mm |
β = 92.60 (3)° |
Rigaku R-AXIS SPIDER diffractometer | 2410 independent reflections |
Absorption correction: multi-scan Higashi (1995) | 1444 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.983 | Rint = 0.025 |
10361 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.257 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.24 e Å−3 |
2410 reflections | Δρmin = −0.22 e Å−3 |
137 parameters |
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 | ||
O1 | 0.25512 (14) | 0.1587 (4) | 0.82721 (12) | 0.0768 (6) | |
O2 | 0.46364 (16) | 0.6933 (5) | 0.89829 (16) | 0.0964 (8) | |
N1 | 0.19230 (16) | 0.2155 (5) | 0.89941 (16) | 0.0764 (7) | |
C1 | 0.1178 (3) | 0.6683 (8) | 1.0260 (2) | 0.1056 (12) | |
H1 | 0.1011 | 0.7383 | 0.9678 | 0.127* | |
C2 | 0.0734 (3) | 0.7530 (11) | 1.1046 (3) | 0.1268 (16) | |
H2 | 0.0286 | 0.8828 | 1.0989 | 0.152* | |
C3 | 0.0946 (3) | 0.6488 (8) | 1.1894 (2) | 0.0954 (11) | |
H3 | 0.0626 | 0.7004 | 1.2417 | 0.114* | |
C4 | 0.1624 (4) | 0.4698 (8) | 1.1971 (2) | 0.1256 (16) | |
H4 | 0.1793 | 0.4015 | 1.2556 | 0.151* | |
C5 | 0.2073 (4) | 0.3863 (7) | 1.1188 (2) | 0.1178 (15) | |
H5 | 0.2535 | 0.2602 | 1.1250 | 0.141* | |
C6 | 0.18481 (17) | 0.4861 (5) | 1.03262 (16) | 0.0601 (6) | |
C7 | 0.23385 (16) | 0.3934 (5) | 0.94913 (15) | 0.0572 (6) | |
C8 | 0.32306 (15) | 0.4644 (4) | 0.91255 (14) | 0.0536 (6) | |
C9 | 0.39362 (17) | 0.6557 (5) | 0.94341 (16) | 0.0607 (6) | |
C10 | 0.3788 (2) | 0.8049 (6) | 1.0298 (2) | 0.0759 (8) | |
H10C | 0.4307 | 0.9216 | 1.0404 | 0.114* | |
H10B | 0.3759 | 0.6913 | 1.0823 | 0.114* | |
H10A | 0.3204 | 0.8984 | 1.0226 | 0.114* | |
C11 | 0.33123 (17) | 0.3083 (5) | 0.83683 (15) | 0.0596 (6) | |
C12 | 0.4041 (2) | 0.2697 (6) | 0.76707 (18) | 0.0747 (8) | |
H12C | 0.3831 | 0.1407 | 0.7232 | 0.112* | |
H12B | 0.4626 | 0.2171 | 0.7984 | 0.112* | |
H12A | 0.4141 | 0.4264 | 0.7342 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0791 (12) | 0.0874 (13) | 0.0643 (11) | −0.0131 (10) | 0.0068 (9) | −0.0224 (9) |
O2 | 0.0895 (15) | 0.1154 (17) | 0.0872 (14) | −0.0362 (12) | 0.0347 (12) | −0.0201 (12) |
N1 | 0.0676 (13) | 0.0920 (16) | 0.0700 (14) | −0.0163 (12) | 0.0102 (11) | −0.0163 (12) |
C1 | 0.097 (2) | 0.149 (3) | 0.0723 (18) | 0.047 (2) | 0.0205 (16) | 0.013 (2) |
C2 | 0.100 (3) | 0.185 (4) | 0.098 (3) | 0.049 (3) | 0.031 (2) | −0.010 (3) |
C3 | 0.093 (2) | 0.114 (3) | 0.083 (2) | −0.023 (2) | 0.0432 (17) | −0.0238 (18) |
C4 | 0.200 (5) | 0.117 (3) | 0.0626 (18) | 0.023 (3) | 0.041 (2) | 0.0083 (19) |
C5 | 0.189 (4) | 0.109 (3) | 0.0579 (16) | 0.054 (3) | 0.031 (2) | 0.0109 (17) |
C6 | 0.0593 (13) | 0.0657 (13) | 0.0562 (12) | −0.0088 (11) | 0.0110 (9) | −0.0029 (10) |
C7 | 0.0600 (13) | 0.0618 (13) | 0.0495 (11) | −0.0031 (10) | 0.0014 (9) | −0.0015 (10) |
C8 | 0.0594 (12) | 0.0574 (12) | 0.0443 (10) | −0.0003 (9) | 0.0039 (8) | 0.0016 (9) |
C9 | 0.0608 (13) | 0.0638 (13) | 0.0580 (13) | −0.0030 (10) | 0.0079 (10) | 0.0016 (10) |
C10 | 0.0687 (16) | 0.0788 (17) | 0.0808 (17) | −0.0105 (13) | 0.0092 (13) | −0.0204 (14) |
C11 | 0.0646 (14) | 0.0658 (13) | 0.0481 (11) | 0.0042 (11) | 0.0014 (10) | −0.0008 (10) |
C12 | 0.0772 (17) | 0.0907 (19) | 0.0568 (13) | 0.0156 (14) | 0.0102 (12) | −0.0067 (13) |
O1—C11 | 1.331 (3) | C5—H5 | 0.9300 |
O1—N1 | 1.421 (3) | C6—C7 | 1.487 (3) |
O2—C9 | 1.219 (3) | C7—C8 | 1.432 (3) |
N1—C7 | 1.297 (3) | C8—C11 | 1.366 (3) |
C1—C6 | 1.344 (4) | C8—C9 | 1.467 (3) |
C1—C2 | 1.383 (5) | C9—C10 | 1.484 (4) |
C1—H1 | 0.9300 | C10—H10C | 0.9600 |
C2—C3 | 1.350 (6) | C10—H10B | 0.9600 |
C2—H2 | 0.9300 | C10—H10A | 0.9600 |
C3—C4 | 1.341 (5) | C11—C12 | 1.477 (3) |
C3—H3 | 0.9300 | C12—H12C | 0.9600 |
C4—C5 | 1.381 (5) | C12—H12B | 0.9600 |
C4—H4 | 0.9300 | C12—H12A | 0.9600 |
C5—C6 | 1.362 (4) | ||
C11—O1—N1 | 109.08 (17) | C8—C7—C6 | 130.9 (2) |
C7—N1—O1 | 105.53 (19) | C11—C8—C7 | 103.9 (2) |
C6—C1—C2 | 121.0 (3) | C11—C8—C9 | 124.6 (2) |
C6—C1—H1 | 119.5 | C7—C8—C9 | 131.5 (2) |
C2—C1—H1 | 119.5 | O2—C9—C8 | 120.4 (2) |
C3—C2—C1 | 120.5 (4) | O2—C9—C10 | 120.1 (2) |
C3—C2—H2 | 119.8 | C8—C9—C10 | 119.5 (2) |
C1—C2—H2 | 119.8 | C9—C10—H10C | 109.5 |
C4—C3—C2 | 119.1 (3) | C9—C10—H10B | 109.5 |
C4—C3—H3 | 120.5 | H10C—C10—H10B | 109.5 |
C2—C3—H3 | 120.5 | C9—C10—H10A | 109.5 |
C3—C4—C5 | 120.4 (4) | H10C—C10—H10A | 109.5 |
C3—C4—H4 | 119.8 | H10B—C10—H10A | 109.5 |
C5—C4—H4 | 119.8 | O1—C11—C8 | 109.8 (2) |
C6—C5—C4 | 120.9 (4) | O1—C11—C12 | 115.5 (2) |
C6—C5—H5 | 119.5 | C8—C11—C12 | 134.6 (2) |
C4—C5—H5 | 119.5 | C11—C12—H12C | 109.5 |
C1—C6—C5 | 118.1 (3) | C11—C12—H12B | 109.5 |
C1—C6—C7 | 121.8 (2) | H12C—C12—H12B | 109.5 |
C5—C6—C7 | 120.1 (3) | C11—C12—H12A | 109.5 |
N1—C7—C8 | 111.7 (2) | H12C—C12—H12A | 109.5 |
N1—C7—C6 | 117.4 (2) | H12B—C12—H12A | 109.5 |
C11—O1—N1—C7 | −0.6 (3) | N1—C7—C8—C11 | −0.9 (3) |
C6—C1—C2—C3 | −1.9 (7) | C6—C7—C8—C11 | 178.0 (2) |
C1—C2—C3—C4 | 2.9 (7) | N1—C7—C8—C9 | 179.0 (2) |
C2—C3—C4—C5 | −2.5 (7) | C6—C7—C8—C9 | −2.1 (4) |
C3—C4—C5—C6 | 1.0 (8) | C11—C8—C9—O2 | 3.5 (4) |
C2—C1—C6—C5 | 0.4 (6) | C7—C8—C9—O2 | −176.3 (3) |
C2—C1—C6—C7 | −179.6 (4) | C11—C8—C9—C10 | −176.9 (2) |
C4—C5—C6—C1 | 0.1 (7) | C7—C8—C9—C10 | 3.3 (4) |
C4—C5—C6—C7 | −179.9 (4) | N1—O1—C11—C8 | 0.1 (3) |
O1—N1—C7—C8 | 0.9 (3) | N1—O1—C11—C12 | 179.3 (2) |
O1—N1—C7—C6 | −178.2 (2) | C7—C8—C11—O1 | 0.4 (3) |
C1—C6—C7—N1 | −85.0 (4) | C9—C8—C11—O1 | −179.4 (2) |
C5—C6—C7—N1 | 95.1 (4) | C7—C8—C11—C12 | −178.6 (3) |
C1—C6—C7—C8 | 96.2 (4) | C9—C8—C11—C12 | 1.5 (4) |
C5—C6—C7—C8 | −83.8 (4) |
Experimental details
Crystal data | |
Chemical formula | C12H11NO2 |
Mr | 201.22 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 14.090 (3), 5.2504 (11), 14.280 (3) |
β (°) | 92.60 (3) |
V (Å3) | 1055.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.70 × 0.50 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS SPIDER |
Absorption correction | Multi-scan Higashi (1995) |
Tmin, Tmax | 0.942, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10361, 2410, 1444 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.257, 1.05 |
No. of reflections | 2410 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.22 |
Computer programs: RAPID-AUTO (Rigaku 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXL97.
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).