organic compounds
3-Benzyl-5-methyl-1,2-benzoxazole 2-oxide
aDepartment of Physics, Kunthavai Naachiar Government Arts College (w) (Autonomous), Thanjavur-7, India, and bR & D Department, Suven Life Sciences Ltd, Hyderabad-55, Andhra Pradesh, India
*Correspondence e-mail: vasuki.arasi@yahoo.com
In the title compound, C15H13NO2, the isoxazole unit and the attached benzene ring are almost coplanar, making a dihedral angle of 1.42 (8)°. The benzyl ring is inclined to the isoxazole ring by 74.19 (8)° and is in a +sc conformation with respect to the benzisoxazole unit. In the crystal, C—H⋯O hydrogen bonds link the molecules, forming zigzag chains propagating along the b axis. There are also π–π interactions present involving the isoxazole and benzyl rings [centroid–centroid distance = 3.5209 (10) Å], and C—H⋯π interactions involving the benzene ring of the benzoisoxazole unit and the methylene bridging group.
Related literature
For the anti-epileptic, antispasmodic and antifungal properties of benzoxazole derivatives, see: Jian et al. (2007). For their antituberculer activity, see: Vinšová et al. (2007). For other biological activties of isoxazoles and benzisoxazole derivatives, see: Veera Reddy et al. (2011). For details of the synthesis, see: Veera Reddy et al. (2011). For the related structure 5-chloro-3-methyl-1,2-benzisoxazole-2-oxide, see: Ghari & Viterbo (1982).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S160053681203838X/su2493sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203838X/su2493Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681203838X/su2493Isup3.cml
All the H atoms were positioned geometrically and treated as riding atoms: C—H = 0.93, 0.96 and 0.97 Å for CH, CH3 and CH2 H atoms, respectively, with Uiso(H) = k × Ueq(C), where k = 1.5 for CH3 H atoms and = 1.2 for other H atoms.
Isoxazoles and benzisoxazoles are important classes of nitrogen-oxygen containing heterocycles. They have extensive biological applications and are useful intermediates in medicinal chemistry (Veera Reddy et al., 2011). The benzoxazole skeleton is an essential structural unit of several antibacterial, anticancer and anti-HIV-1 agents. The antituberculotic activity of several benzoxazole derivatives have been reported (Vinšová et al., 2007). Some benzoxazoles exhibit high fluorescence and are used as optical whitening agents, photoluminesents and active components in dye lasers. Benzoxazole derivatives show antiepileptic, antispasmodic and antifungal properties (Jian et al., 2007). 3-substituted 1,2-benzisoxazole derivatives are emerging as potential antipsychotic compounds, antiseizure agents and are also used to block the repetitive firing of voltage-sensitive sodium channels and so reduce voltage-sensitive T-type calcium currents (Veera Reddy et al., 2011).
The molecular structure of the title functionalized 1,2-benzisoxazole compound is illustrated in Fig. 1. It contains three planar rings, namely, a methyl substituted benzene ring A = C2—C7, an isoxazole ring B =C1/C7/C6/O1/N1 and the benzyl ring C = C9—C14. The dihedral angles between rings A/B and B/C are 1.42 (8)° and 74.19 (8)°, respectively.
The bond lengths and angles in the title compound are in good agreement with the expected values and are comparable with the corresponding values reported for 5-chloro-3-methyl-1,2-benzisoxazole-2-oxide (Ghari & Viterbo, 1982).
In the crystal, molecules are linked via C—H···O hydrogen bonds leading to the formation of zigzag chains propagating along the a axis direction (Tabel 1 and Fig. 2). Molecules are also linked via C—H···π (Table 1) and π···π interactions. The latter involve the isoxazole (B = Cg1) and benzyl rings (C = Cg3) [Cg1···Cg3i = 3.5209 (10) Å; symmetry code: (i) -x + 1.5, y - 1/2, -z + 1/2].
For the anti-epileptic, antispasmodic and antifungal properties of benzoxazole derivatives, see: Jian et al. (2007). For their antituberculer activity, see: Vinšová et al. (2007). For other biological activties of isoxazoles and benzisoxazole derivatives, see: Veera Reddy et al. (2011). For details of the synthesis, see: Veera Reddy et al. (2011). For the related structure 5-chloro-3-methyl-1,2-benzisoxazole-2-oxide, see: Ghari & Viterbo (1982).
Data collection: APEX2 (Bruker, 2004); cell
SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).C15H13NO2 | F(000) = 504 |
Mr = 239.26 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 13955 reflections |
a = 6.4527 (2) Å | θ = 1.2–30.1° |
b = 11.2213 (4) Å | µ = 0.09 mm−1 |
c = 16.9371 (7) Å | T = 293 K |
β = 100.002 (2)° | Block, colourless |
V = 1207.74 (8) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3512 independent reflections |
Radiation source: fine-focus sealed tube | 2113 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and φ scan | θmax = 30.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −9→8 |
Tmin = 0.974, Tmax = 0.983 | k = −15→13 |
13491 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0836P)2 + 0.1125P] where P = (Fo2 + 2Fc2)/3 |
3512 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C15H13NO2 | V = 1207.74 (8) Å3 |
Mr = 239.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.4527 (2) Å | µ = 0.09 mm−1 |
b = 11.2213 (4) Å | T = 293 K |
c = 16.9371 (7) Å | 0.30 × 0.20 × 0.20 mm |
β = 100.002 (2)° |
Bruker Kappa APEXII CCD diffractometer | 3512 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2113 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.983 | Rint = 0.026 |
13491 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.26 e Å−3 |
3512 reflections | Δρmin = −0.20 e Å−3 |
163 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.28937 (17) | 0.48425 (11) | 0.21034 (8) | 0.0760 (5) | |
O2 | 0.3491 (2) | 0.63946 (12) | 0.29866 (9) | 0.0979 (6) | |
N1 | 0.4211 (2) | 0.58198 (13) | 0.24703 (9) | 0.0682 (5) | |
C1 | 0.5941 (2) | 0.58880 (13) | 0.21630 (9) | 0.0532 (5) | |
C2 | 0.7187 (2) | 0.46425 (12) | 0.10447 (8) | 0.0508 (4) | |
C3 | 0.6602 (3) | 0.37116 (13) | 0.05213 (9) | 0.0577 (5) | |
C4 | 0.4707 (3) | 0.31228 (14) | 0.05425 (11) | 0.0688 (6) | |
C5 | 0.3391 (3) | 0.34234 (15) | 0.10596 (12) | 0.0728 (6) | |
C6 | 0.3994 (2) | 0.43709 (14) | 0.15601 (10) | 0.0590 (5) | |
C7 | 0.5868 (2) | 0.49807 (12) | 0.15712 (9) | 0.0485 (4) | |
C8 | 0.7549 (2) | 0.68132 (13) | 0.24347 (9) | 0.0574 (5) | |
C9 | 0.7396 (2) | 0.78613 (12) | 0.18692 (8) | 0.0492 (4) | |
C10 | 0.5636 (2) | 0.85898 (13) | 0.17589 (9) | 0.0578 (5) | |
C11 | 0.5506 (3) | 0.95583 (15) | 0.12500 (11) | 0.0685 (6) | |
C12 | 0.7117 (3) | 0.98059 (16) | 0.08532 (11) | 0.0753 (7) | |
C13 | 0.8872 (3) | 0.90974 (17) | 0.09595 (11) | 0.0747 (7) | |
C14 | 0.9005 (2) | 0.81256 (15) | 0.14674 (10) | 0.0615 (5) | |
C15 | 0.7953 (3) | 0.33322 (18) | −0.00672 (11) | 0.0800 (7) | |
H2 | 0.84520 | 0.50400 | 0.10450 | 0.0610* | |
H4 | 0.43230 | 0.24970 | 0.01870 | 0.0830* | |
H5 | 0.21500 | 0.30080 | 0.10730 | 0.0870* | |
H8A | 0.89380 | 0.64610 | 0.24820 | 0.0690* | |
H8B | 0.73800 | 0.70920 | 0.29620 | 0.0690* | |
H10 | 0.45330 | 0.84250 | 0.20300 | 0.0690* | |
H11 | 0.43170 | 1.00420 | 0.11780 | 0.0820* | |
H12 | 0.70270 | 1.04570 | 0.05090 | 0.0900* | |
H13 | 0.99740 | 0.92700 | 0.06900 | 0.0900* | |
H14 | 1.02000 | 0.76470 | 0.15370 | 0.0740* | |
H15A | 0.72950 | 0.26790 | −0.03810 | 0.1200* | |
H15B | 0.93050 | 0.30870 | 0.02160 | 0.1200* | |
H15C | 0.81250 | 0.39870 | −0.04150 | 0.1200* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0529 (6) | 0.0788 (8) | 0.1006 (10) | −0.0032 (6) | 0.0250 (6) | 0.0178 (7) |
O2 | 0.0986 (10) | 0.0965 (10) | 0.1127 (11) | 0.0202 (8) | 0.0581 (9) | −0.0021 (9) |
N1 | 0.0641 (8) | 0.0666 (9) | 0.0788 (9) | 0.0092 (7) | 0.0262 (7) | 0.0079 (7) |
C1 | 0.0519 (8) | 0.0538 (8) | 0.0546 (8) | 0.0049 (6) | 0.0116 (6) | 0.0101 (6) |
C2 | 0.0481 (7) | 0.0505 (8) | 0.0512 (8) | −0.0029 (6) | 0.0018 (6) | 0.0074 (6) |
C3 | 0.0650 (9) | 0.0501 (8) | 0.0521 (8) | 0.0031 (7) | −0.0065 (7) | 0.0055 (6) |
C4 | 0.0748 (11) | 0.0507 (9) | 0.0710 (11) | −0.0063 (8) | −0.0148 (9) | 0.0047 (8) |
C5 | 0.0573 (9) | 0.0597 (10) | 0.0930 (13) | −0.0181 (8) | −0.0100 (9) | 0.0202 (9) |
C6 | 0.0467 (7) | 0.0582 (9) | 0.0708 (10) | −0.0024 (7) | 0.0062 (7) | 0.0187 (7) |
C7 | 0.0439 (7) | 0.0472 (7) | 0.0524 (8) | −0.0022 (6) | 0.0025 (6) | 0.0115 (6) |
C8 | 0.0628 (8) | 0.0557 (8) | 0.0516 (8) | 0.0011 (7) | 0.0040 (6) | −0.0009 (6) |
C9 | 0.0541 (7) | 0.0468 (7) | 0.0451 (7) | −0.0011 (6) | 0.0041 (6) | −0.0098 (6) |
C10 | 0.0552 (8) | 0.0563 (9) | 0.0607 (9) | 0.0023 (7) | 0.0065 (7) | −0.0086 (7) |
C11 | 0.0730 (10) | 0.0533 (9) | 0.0724 (11) | 0.0085 (8) | −0.0059 (9) | −0.0047 (8) |
C12 | 0.0993 (14) | 0.0570 (10) | 0.0650 (11) | −0.0094 (10) | 0.0017 (10) | 0.0035 (8) |
C13 | 0.0853 (12) | 0.0712 (11) | 0.0713 (11) | −0.0149 (10) | 0.0242 (9) | −0.0008 (9) |
C14 | 0.0574 (8) | 0.0609 (9) | 0.0676 (10) | 0.0022 (7) | 0.0149 (7) | −0.0056 (7) |
C15 | 0.0952 (13) | 0.0782 (11) | 0.0626 (11) | 0.0089 (10) | 0.0024 (9) | −0.0121 (9) |
O1—N1 | 1.4587 (19) | C11—C12 | 1.361 (3) |
O1—C6 | 1.363 (2) | C12—C13 | 1.370 (3) |
O2—N1 | 1.240 (2) | C13—C14 | 1.382 (3) |
N1—C1 | 1.3133 (19) | C2—H2 | 0.9300 |
C1—C7 | 1.424 (2) | C4—H4 | 0.9300 |
C1—C8 | 1.483 (2) | C5—H5 | 0.9300 |
C2—C3 | 1.380 (2) | C8—H8A | 0.9700 |
C2—C7 | 1.3883 (19) | C8—H8B | 0.9700 |
C3—C4 | 1.396 (3) | C10—H10 | 0.9300 |
C3—C15 | 1.496 (3) | C11—H11 | 0.9300 |
C4—C5 | 1.364 (3) | C12—H12 | 0.9300 |
C5—C6 | 1.373 (2) | C13—H13 | 0.9300 |
C6—C7 | 1.3867 (19) | C14—H14 | 0.9300 |
C8—C9 | 1.509 (2) | C15—H15A | 0.9600 |
C9—C10 | 1.3854 (19) | C15—H15B | 0.9600 |
C9—C14 | 1.3691 (19) | C15—H15C | 0.9600 |
C10—C11 | 1.381 (2) | ||
N1—O1—C6 | 104.25 (11) | C3—C2—H2 | 120.00 |
O1—N1—O2 | 115.44 (12) | C7—C2—H2 | 120.00 |
O1—N1—C1 | 110.34 (13) | C3—C4—H4 | 118.00 |
O2—N1—C1 | 134.23 (15) | C5—C4—H4 | 118.00 |
N1—C1—C7 | 108.11 (13) | C4—C5—H5 | 122.00 |
N1—C1—C8 | 120.98 (13) | C6—C5—H5 | 122.00 |
C7—C1—C8 | 130.90 (12) | C1—C8—H8A | 109.00 |
C3—C2—C7 | 119.33 (14) | C1—C8—H8B | 109.00 |
C2—C3—C4 | 119.02 (15) | C9—C8—H8A | 109.00 |
C2—C3—C15 | 121.18 (16) | C9—C8—H8B | 109.00 |
C4—C3—C15 | 119.81 (15) | H8A—C8—H8B | 108.00 |
C3—C4—C5 | 123.05 (16) | C9—C10—H10 | 120.00 |
C4—C5—C6 | 116.53 (16) | C11—C10—H10 | 120.00 |
O1—C6—C5 | 126.33 (14) | C10—C11—H11 | 120.00 |
O1—C6—C7 | 110.76 (13) | C12—C11—H11 | 120.00 |
C5—C6—C7 | 122.91 (15) | C11—C12—H12 | 120.00 |
C1—C7—C2 | 134.32 (13) | C13—C12—H12 | 120.00 |
C1—C7—C6 | 106.53 (12) | C12—C13—H13 | 120.00 |
C2—C7—C6 | 119.13 (13) | C14—C13—H13 | 120.00 |
C1—C8—C9 | 112.55 (12) | C9—C14—H14 | 120.00 |
C8—C9—C10 | 120.48 (12) | C13—C14—H14 | 120.00 |
C8—C9—C14 | 120.84 (12) | C3—C15—H15A | 109.00 |
C10—C9—C14 | 118.67 (13) | C3—C15—H15B | 109.00 |
C9—C10—C11 | 120.54 (14) | C3—C15—H15C | 110.00 |
C10—C11—C12 | 120.02 (17) | H15A—C15—H15B | 110.00 |
C11—C12—C13 | 120.11 (17) | H15A—C15—H15C | 109.00 |
C12—C13—C14 | 120.02 (17) | H15B—C15—H15C | 110.00 |
C9—C14—C13 | 120.65 (14) | ||
C6—O1—N1—O2 | 179.19 (14) | C2—C3—C4—C5 | 0.0 (3) |
C6—O1—N1—C1 | −0.63 (17) | C3—C4—C5—C6 | 1.5 (3) |
N1—O1—C6—C5 | −179.86 (16) | C4—C5—C6—C7 | −2.1 (3) |
N1—O1—C6—C7 | 0.19 (16) | C4—C5—C6—O1 | 177.92 (16) |
O1—N1—C1—C7 | 0.80 (17) | O1—C6—C7—C1 | 0.26 (17) |
O2—N1—C1—C8 | 0.1 (3) | O1—C6—C7—C2 | −178.71 (13) |
O2—N1—C1—C7 | −178.98 (18) | C5—C6—C7—C1 | −179.69 (16) |
O1—N1—C1—C8 | 179.89 (12) | C5—C6—C7—C2 | 1.3 (2) |
C8—C1—C7—C2 | −0.9 (3) | C1—C8—C9—C10 | 65.02 (17) |
C8—C1—C7—C6 | −179.63 (15) | C1—C8—C9—C14 | −116.26 (15) |
N1—C1—C8—C9 | −99.68 (17) | C8—C9—C10—C11 | 179.13 (14) |
C7—C1—C8—C9 | 79.18 (19) | C14—C9—C10—C11 | 0.4 (2) |
N1—C1—C7—C6 | −0.66 (17) | C8—C9—C14—C13 | −178.99 (15) |
N1—C1—C7—C2 | 178.08 (16) | C10—C9—C14—C13 | −0.2 (2) |
C7—C2—C3—C15 | 178.79 (14) | C9—C10—C11—C12 | −0.2 (3) |
C7—C2—C3—C4 | −0.8 (2) | C10—C11—C12—C13 | −0.2 (3) |
C3—C2—C7—C6 | 0.2 (2) | C11—C12—C13—C14 | 0.3 (3) |
C3—C2—C7—C1 | −178.40 (16) | C12—C13—C14—C9 | −0.1 (3) |
C15—C3—C4—C5 | −179.66 (17) |
Cg2 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.93 | 2.49 | 3.154 (2) | 128 |
C8—H8B···Cg2ii | 0.97 | 3.00 | 3.6800 (16) | 129 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H13NO2 |
Mr | 239.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.4527 (2), 11.2213 (4), 16.9371 (7) |
β (°) | 100.002 (2) |
V (Å3) | 1207.74 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.974, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13491, 3512, 2113 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.172, 1.06 |
No. of reflections | 3512 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.20 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX publication routines (Farrugia, 1999).
Cg2 is the centroid of the C2–C7 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.93 | 2.49 | 3.154 (2) | 128 |
C8—H8B···Cg2ii | 0.97 | 3.00 | 3.6800 (16) | 129 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
The authors thank the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai-36, for the data collection.
References
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Isoxazoles and benzisoxazoles are important classes of nitrogen-oxygen containing heterocycles. They have extensive biological applications and are useful intermediates in medicinal chemistry (Veera Reddy et al., 2011). The benzoxazole skeleton is an essential structural unit of several antibacterial, anticancer and anti-HIV-1 agents. The antituberculotic activity of several benzoxazole derivatives have been reported (Vinšová et al., 2007). Some benzoxazoles exhibit high fluorescence and are used as optical whitening agents, photoluminesents and active components in dye lasers. Benzoxazole derivatives show antiepileptic, antispasmodic and antifungal properties (Jian et al., 2007). 3-substituted 1,2-benzisoxazole derivatives are emerging as potential antipsychotic compounds, antiseizure agents and are also used to block the repetitive firing of voltage-sensitive sodium channels and so reduce voltage-sensitive T-type calcium currents (Veera Reddy et al., 2011).
The molecular structure of the title functionalized 1,2-benzisoxazole compound is illustrated in Fig. 1. It contains three planar rings, namely, a methyl substituted benzene ring A = C2—C7, an isoxazole ring B =C1/C7/C6/O1/N1 and the benzyl ring C = C9—C14. The dihedral angles between rings A/B and B/C are 1.42 (8)° and 74.19 (8)°, respectively.
The bond lengths and angles in the title compound are in good agreement with the expected values and are comparable with the corresponding values reported for 5-chloro-3-methyl-1,2-benzisoxazole-2-oxide (Ghari & Viterbo, 1982).
In the crystal, molecules are linked via C—H···O hydrogen bonds leading to the formation of zigzag chains propagating along the a axis direction (Tabel 1 and Fig. 2). Molecules are also linked via C—H···π (Table 1) and π···π interactions. The latter involve the isoxazole (B = Cg1) and benzyl rings (C = Cg3) [Cg1···Cg3i = 3.5209 (10) Å; symmetry code: (i) -x + 1.5, y - 1/2, -z + 1/2].