organic compounds
Methyl 1-phenyl-3-p-tolyl-1,9b-dihydro-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxylate
aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: aravindhanpresidency@gmail.com
In the title compound, C25H23NO4, the pyran ring of the chroman moiety has an with the methylene C atom as the flap. The isoxazole ring has a twist conformation on the O—C bond. The dihedral angle between their mean planes is 57.87 (9)°. The attached phenyl and benzene rings are twisted away from its mean plane by 56.19 (10) and 50.57 (10)°, respectively. These two rings are normal to each other, subtending a dihedral angle of 89.2 (1)°. In the crystal, there are no classical hydrogen bonds; the molecules are linked via C—H⋯π interactions, forming a two-dimensional network lying parallel to (10-1).
CCDC reference: 984809
Related literature
For the biological activity of isoxazoline derivatives, see: Kozikowski (1984); Howe & Shelton (1990); Bakthadoss & Murugan (2010). For the synthesis of chromenoisoxazolidines by intramolecular 1,3-dipolar cycloadditions, see: Bakthadoss & Murugan (2010). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For standard bond lengths, see: Allen et al. (1987).
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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 984809
10.1107/S1600536814002438/su2676sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002438/su2676Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002438/su2676Isup3.cml
The title compound was synthesized according to the published procedure (Bakthadoss & Murugan, 2010). A mixture of (E)- methyl 2-((2-formylphenoxy)methyl)-3-p-tolylacrylate (2 mmol, 0.60 g) and N-phenylhydroxylamine (3 mmol, 0.33 g) in ethanol (10 ml) was refluxed for 6 h. After the completion of the reaction, as indicated by TLC, the reaction mixture was concentrated under reduced pressure and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 × 15 ml). The organic layers were combined and washed with brine (3 × 15 ml) and dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The crude mass was purified by
on silica gel (Acme 100–200 mesh), using ethyl acetate-hexane (0.5: 9.5) to afford the pure compound as a colourless solid in 92% yield. Colourless block-like crystals were obtained by slow evaporation of a solution in ethyl acetate-hexane (0.5: 9.5).N and C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: N-H = 0. \%A, C–H = 0.93–0.98 Å, with Uiso(H) =1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecule, with atom labelling. The displacement ellipsoids are drawn at 30% probability level. the H atoms have been omitted for clarity. |
C25H23NO4 | F(000) = 848 |
Mr = 401.44 | Dx = 1.310 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3415 reflections |
a = 14.0674 (7) Å | θ = 1.6–28.4° |
b = 7.8105 (4) Å | µ = 0.09 mm−1 |
c = 19.7680 (9) Å | T = 293 K |
β = 110.456 (3)° | Block, colourless |
V = 2035.01 (17) Å3 | 0.22 × 0.19 × 0.17 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 5086 independent reflections |
Radiation source: fine-focus sealed tube | 3415 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω and φ scans | θmax = 28.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −18→16 |
Tmin = 0.981, Tmax = 0.985 | k = −10→8 |
18922 measured reflections | l = −26→26 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0678P)2 + 0.5852P] where P = (Fo2 + 2Fc2)/3 |
5086 reflections | (Δ/σ)max < 0.001 |
273 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C25H23NO4 | V = 2035.01 (17) Å3 |
Mr = 401.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.0674 (7) Å | µ = 0.09 mm−1 |
b = 7.8105 (4) Å | T = 293 K |
c = 19.7680 (9) Å | 0.22 × 0.19 × 0.17 mm |
β = 110.456 (3)° |
Bruker SMART APEXII CCD diffractometer | 5086 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3415 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.985 | Rint = 0.035 |
18922 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.35 e Å−3 |
5086 reflections | Δρmin = −0.39 e Å−3 |
273 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 | ||
C1 | 0.28173 (13) | 0.2285 (2) | 0.03324 (9) | 0.0428 (4) | |
C2 | 0.21242 (16) | 0.2949 (3) | −0.03043 (10) | 0.0549 (5) | |
H2 | 0.1432 | 0.2921 | −0.0385 | 0.066* | |
C3 | 0.24774 (18) | 0.3646 (3) | −0.08108 (10) | 0.0641 (6) | |
H3 | 0.2020 | 0.4092 | −0.1236 | 0.077* | |
C4 | 0.35030 (19) | 0.3690 (3) | −0.06946 (10) | 0.0610 (6) | |
H4 | 0.3737 | 0.4181 | −0.1036 | 0.073* | |
C5 | 0.41795 (16) | 0.3000 (2) | −0.00667 (10) | 0.0499 (5) | |
H5 | 0.4870 | 0.3013 | 0.0007 | 0.060* | |
C6 | 0.38480 (13) | 0.2284 (2) | 0.04573 (9) | 0.0396 (4) | |
C7 | 0.46000 (12) | 0.1483 (2) | 0.11273 (8) | 0.0362 (4) | |
H7 | 0.4920 | 0.0503 | 0.0983 | 0.043* | |
C8 | 0.41150 (12) | 0.0860 (2) | 0.16788 (8) | 0.0354 (4) | |
C9 | 0.31056 (13) | 0.1770 (2) | 0.15550 (9) | 0.0433 (4) | |
H9A | 0.2788 | 0.1283 | 0.1874 | 0.052* | |
H9B | 0.3234 | 0.2971 | 0.1677 | 0.052* | |
C10 | 0.49094 (12) | 0.1477 (2) | 0.24007 (8) | 0.0363 (4) | |
H10 | 0.5482 | 0.0676 | 0.2548 | 0.044* | |
C11 | 0.64415 (12) | 0.2269 (2) | 0.16687 (9) | 0.0366 (4) | |
C12 | 0.67274 (15) | 0.1419 (2) | 0.11511 (10) | 0.0486 (4) | |
H12 | 0.6236 | 0.1026 | 0.0729 | 0.058* | |
C13 | 0.77511 (17) | 0.1158 (3) | 0.12682 (13) | 0.0592 (6) | |
H13 | 0.7940 | 0.0584 | 0.0923 | 0.071* | |
C14 | 0.84856 (16) | 0.1735 (3) | 0.18855 (13) | 0.0594 (5) | |
H14 | 0.9168 | 0.1567 | 0.1956 | 0.071* | |
C15 | 0.82042 (14) | 0.2561 (3) | 0.23968 (12) | 0.0544 (5) | |
H15 | 0.8701 | 0.2944 | 0.2818 | 0.065* | |
C16 | 0.71910 (13) | 0.2836 (2) | 0.22953 (10) | 0.0435 (4) | |
H16 | 0.7012 | 0.3401 | 0.2647 | 0.052* | |
C17 | 0.45771 (12) | 0.1822 (2) | 0.30376 (8) | 0.0387 (4) | |
C18 | 0.43833 (14) | 0.3468 (2) | 0.32141 (10) | 0.0469 (4) | |
H18 | 0.4412 | 0.4378 | 0.2919 | 0.056* | |
C19 | 0.41461 (14) | 0.3771 (3) | 0.38296 (10) | 0.0529 (5) | |
H19 | 0.4031 | 0.4887 | 0.3946 | 0.063* | |
C20 | 0.40780 (14) | 0.2438 (3) | 0.42726 (10) | 0.0526 (5) | |
C21 | 0.42430 (16) | 0.0803 (3) | 0.40799 (10) | 0.0591 (5) | |
H21 | 0.4178 | −0.0114 | 0.4361 | 0.071* | |
C22 | 0.45034 (15) | 0.0490 (3) | 0.34767 (9) | 0.0516 (5) | |
H22 | 0.4630 | −0.0626 | 0.3367 | 0.062* | |
C23 | 0.3852 (2) | 0.2806 (4) | 0.49513 (12) | 0.0751 (7) | |
H23A | 0.3697 | 0.1754 | 0.5142 | 0.113* | |
H23B | 0.3282 | 0.3567 | 0.4840 | 0.113* | |
H23C | 0.4433 | 0.3329 | 0.5303 | 0.113* | |
C24 | 0.39583 (14) | −0.1064 (2) | 0.16638 (9) | 0.0438 (4) | |
C25 | 0.3720 (2) | −0.3606 (3) | 0.09983 (16) | 0.0832 (8) | |
H25A | 0.4320 | −0.4181 | 0.1303 | 0.125* | |
H25B | 0.3570 | −0.3961 | 0.0507 | 0.125* | |
H25C | 0.3161 | −0.3891 | 0.1149 | 0.125* | |
N1 | 0.54050 (10) | 0.27177 (18) | 0.15286 (7) | 0.0368 (3) | |
O1 | 0.24239 (9) | 0.16260 (17) | 0.08243 (6) | 0.0490 (3) | |
O2 | 0.52327 (8) | 0.30692 (14) | 0.21877 (6) | 0.0401 (3) | |
O3 | 0.3903 (2) | −0.1874 (2) | 0.21509 (9) | 0.1145 (9) | |
O4 | 0.38844 (14) | −0.17740 (17) | 0.10527 (8) | 0.0697 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0519 (10) | 0.0355 (9) | 0.0363 (8) | −0.0049 (7) | 0.0094 (7) | −0.0022 (7) |
C2 | 0.0565 (11) | 0.0533 (12) | 0.0436 (10) | 0.0008 (9) | 0.0034 (8) | −0.0021 (8) |
C3 | 0.0841 (16) | 0.0579 (13) | 0.0360 (9) | 0.0009 (11) | 0.0030 (9) | 0.0054 (9) |
C4 | 0.0884 (16) | 0.0548 (13) | 0.0381 (9) | −0.0088 (11) | 0.0201 (10) | 0.0060 (9) |
C5 | 0.0642 (12) | 0.0465 (11) | 0.0398 (9) | −0.0085 (9) | 0.0190 (8) | −0.0005 (8) |
C6 | 0.0525 (10) | 0.0304 (8) | 0.0339 (8) | −0.0071 (7) | 0.0126 (7) | −0.0040 (6) |
C7 | 0.0435 (9) | 0.0304 (8) | 0.0351 (8) | −0.0050 (7) | 0.0140 (7) | −0.0030 (6) |
C8 | 0.0408 (8) | 0.0336 (9) | 0.0314 (7) | −0.0032 (7) | 0.0123 (6) | −0.0007 (6) |
C9 | 0.0420 (9) | 0.0505 (11) | 0.0367 (8) | −0.0014 (8) | 0.0130 (7) | 0.0019 (7) |
C10 | 0.0375 (8) | 0.0362 (9) | 0.0354 (8) | −0.0007 (7) | 0.0133 (6) | −0.0040 (7) |
C11 | 0.0425 (9) | 0.0313 (8) | 0.0410 (8) | −0.0024 (7) | 0.0208 (7) | 0.0022 (7) |
C12 | 0.0606 (11) | 0.0467 (11) | 0.0483 (10) | −0.0032 (9) | 0.0312 (9) | −0.0022 (8) |
C13 | 0.0742 (14) | 0.0491 (12) | 0.0769 (14) | 0.0044 (10) | 0.0549 (12) | 0.0031 (10) |
C14 | 0.0486 (11) | 0.0531 (12) | 0.0858 (15) | 0.0058 (9) | 0.0350 (11) | 0.0145 (11) |
C15 | 0.0433 (10) | 0.0517 (12) | 0.0670 (12) | −0.0033 (8) | 0.0176 (9) | 0.0066 (10) |
C16 | 0.0437 (9) | 0.0414 (10) | 0.0479 (10) | −0.0033 (7) | 0.0190 (7) | −0.0026 (8) |
C17 | 0.0362 (8) | 0.0455 (10) | 0.0329 (8) | 0.0014 (7) | 0.0103 (6) | −0.0036 (7) |
C18 | 0.0503 (10) | 0.0484 (11) | 0.0460 (10) | 0.0016 (8) | 0.0220 (8) | −0.0058 (8) |
C19 | 0.0502 (10) | 0.0604 (12) | 0.0519 (11) | 0.0054 (9) | 0.0225 (9) | −0.0127 (9) |
C20 | 0.0463 (10) | 0.0751 (14) | 0.0370 (9) | 0.0064 (9) | 0.0155 (7) | −0.0053 (9) |
C21 | 0.0724 (13) | 0.0688 (14) | 0.0397 (10) | 0.0044 (11) | 0.0242 (9) | 0.0074 (9) |
C22 | 0.0664 (12) | 0.0503 (11) | 0.0390 (9) | 0.0066 (9) | 0.0196 (8) | 0.0004 (8) |
C23 | 0.0841 (16) | 0.102 (2) | 0.0469 (11) | 0.0109 (14) | 0.0328 (11) | −0.0068 (12) |
C24 | 0.0516 (10) | 0.0380 (9) | 0.0379 (8) | −0.0074 (8) | 0.0104 (7) | 0.0017 (7) |
C25 | 0.123 (2) | 0.0343 (12) | 0.106 (2) | −0.0138 (12) | 0.0565 (18) | −0.0164 (12) |
N1 | 0.0402 (7) | 0.0371 (7) | 0.0361 (7) | −0.0032 (6) | 0.0169 (6) | −0.0053 (6) |
O1 | 0.0406 (6) | 0.0594 (8) | 0.0419 (6) | −0.0064 (6) | 0.0079 (5) | 0.0042 (6) |
O2 | 0.0450 (6) | 0.0381 (7) | 0.0427 (6) | −0.0064 (5) | 0.0223 (5) | −0.0115 (5) |
O3 | 0.230 (3) | 0.0594 (11) | 0.0599 (11) | −0.0586 (13) | 0.0579 (14) | −0.0059 (8) |
O4 | 0.1217 (13) | 0.0332 (7) | 0.0694 (10) | −0.0144 (8) | 0.0526 (9) | −0.0117 (7) |
C1—O1 | 1.376 (2) | C13—C14 | 1.371 (3) |
C1—C6 | 1.383 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.395 (2) | C14—C15 | 1.369 (3) |
C2—C3 | 1.376 (3) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.385 (2) |
C3—C4 | 1.380 (3) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.383 (3) | C17—C22 | 1.382 (3) |
C4—H4 | 0.9300 | C17—C18 | 1.384 (2) |
C5—C6 | 1.393 (2) | C18—C19 | 1.390 (2) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—C7 | 1.512 (2) | C19—C20 | 1.385 (3) |
C7—N1 | 1.488 (2) | C19—H19 | 0.9300 |
C7—C8 | 1.553 (2) | C20—C21 | 1.376 (3) |
C7—H7 | 0.9800 | C20—C23 | 1.511 (3) |
C8—C24 | 1.518 (2) | C21—C22 | 1.386 (2) |
C8—C9 | 1.529 (2) | C21—H21 | 0.9300 |
C8—C10 | 1.550 (2) | C22—H22 | 0.9300 |
C9—O1 | 1.432 (2) | C23—H23A | 0.9600 |
C9—H9A | 0.9700 | C23—H23B | 0.9600 |
C9—H9B | 0.9700 | C23—H23C | 0.9600 |
C10—O2 | 1.4368 (19) | C24—O3 | 1.178 (2) |
C10—C17 | 1.513 (2) | C24—O4 | 1.300 (2) |
C10—H10 | 0.9800 | C25—O4 | 1.447 (2) |
C11—C16 | 1.389 (2) | C25—H25A | 0.9600 |
C11—C12 | 1.392 (2) | C25—H25B | 0.9600 |
C11—N1 | 1.429 (2) | C25—H25C | 0.9600 |
C12—C13 | 1.391 (3) | N1—O2 | 1.4326 (16) |
C12—H12 | 0.9300 | ||
O1—C1—C6 | 121.96 (15) | C12—C13—H13 | 119.5 |
O1—C1—C2 | 116.73 (16) | C15—C14—C13 | 119.32 (18) |
C6—C1—C2 | 121.31 (17) | C15—C14—H14 | 120.3 |
C3—C2—C1 | 119.17 (19) | C13—C14—H14 | 120.3 |
C3—C2—H2 | 120.4 | C14—C15—C16 | 121.0 (2) |
C1—C2—H2 | 120.4 | C14—C15—H15 | 119.5 |
C2—C3—C4 | 120.76 (18) | C16—C15—H15 | 119.5 |
C2—C3—H3 | 119.6 | C15—C16—C11 | 120.13 (17) |
C4—C3—H3 | 119.6 | C15—C16—H16 | 119.9 |
C3—C4—C5 | 119.41 (19) | C11—C16—H16 | 119.9 |
C3—C4—H4 | 120.3 | C22—C17—C18 | 118.46 (16) |
C5—C4—H4 | 120.3 | C22—C17—C10 | 120.09 (16) |
C4—C5—C6 | 121.32 (19) | C18—C17—C10 | 121.39 (15) |
C4—C5—H5 | 119.3 | C17—C18—C19 | 120.50 (18) |
C6—C5—H5 | 119.3 | C17—C18—H18 | 119.7 |
C1—C6—C5 | 118.01 (16) | C19—C18—H18 | 119.7 |
C1—C6—C7 | 121.70 (15) | C20—C19—C18 | 121.11 (19) |
C5—C6—C7 | 120.26 (16) | C20—C19—H19 | 119.4 |
N1—C7—C6 | 111.58 (13) | C18—C19—H19 | 119.4 |
N1—C7—C8 | 105.54 (12) | C21—C20—C19 | 117.84 (17) |
C6—C7—C8 | 113.59 (13) | C21—C20—C23 | 122.1 (2) |
N1—C7—H7 | 108.7 | C19—C20—C23 | 120.1 (2) |
C6—C7—H7 | 108.7 | C20—C21—C22 | 121.52 (19) |
C8—C7—H7 | 108.7 | C20—C21—H21 | 119.2 |
C24—C8—C9 | 109.67 (14) | C22—C21—H21 | 119.2 |
C24—C8—C10 | 112.27 (13) | C17—C22—C21 | 120.52 (19) |
C9—C8—C10 | 109.47 (13) | C17—C22—H22 | 119.7 |
C24—C8—C7 | 113.13 (13) | C21—C22—H22 | 119.7 |
C9—C8—C7 | 110.69 (13) | C20—C23—H23A | 109.5 |
C10—C8—C7 | 101.35 (12) | C20—C23—H23B | 109.5 |
O1—C9—C8 | 112.46 (14) | H23A—C23—H23B | 109.5 |
O1—C9—H9A | 109.1 | C20—C23—H23C | 109.5 |
C8—C9—H9A | 109.1 | H23A—C23—H23C | 109.5 |
O1—C9—H9B | 109.1 | H23B—C23—H23C | 109.5 |
C8—C9—H9B | 109.1 | O3—C24—O4 | 121.62 (18) |
H9A—C9—H9B | 107.8 | O3—C24—C8 | 124.52 (17) |
O2—C10—C17 | 108.13 (13) | O4—C24—C8 | 113.86 (15) |
O2—C10—C8 | 101.51 (12) | O4—C25—H25A | 109.5 |
C17—C10—C8 | 119.25 (13) | O4—C25—H25B | 109.5 |
O2—C10—H10 | 109.1 | H25A—C25—H25B | 109.5 |
C17—C10—H10 | 109.1 | O4—C25—H25C | 109.5 |
C8—C10—H10 | 109.1 | H25A—C25—H25C | 109.5 |
C16—C11—C12 | 118.91 (16) | H25B—C25—H25C | 109.5 |
C16—C11—N1 | 119.98 (14) | C11—N1—O2 | 110.86 (12) |
C12—C11—N1 | 120.78 (15) | C11—N1—C7 | 118.62 (13) |
C13—C12—C11 | 119.71 (18) | O2—N1—C7 | 105.67 (11) |
C13—C12—H12 | 120.1 | C1—O1—C9 | 112.99 (13) |
C11—C12—H12 | 120.1 | N1—O2—C10 | 105.79 (11) |
C14—C13—C12 | 120.97 (18) | C24—O4—C25 | 116.71 (17) |
C14—C13—H13 | 119.5 | ||
O1—C1—C2—C3 | 179.09 (17) | O2—C10—C17—C22 | −161.69 (15) |
C6—C1—C2—C3 | −1.3 (3) | C8—C10—C17—C22 | 83.2 (2) |
C1—C2—C3—C4 | 0.1 (3) | O2—C10—C17—C18 | 15.5 (2) |
C2—C3—C4—C5 | 1.1 (3) | C8—C10—C17—C18 | −99.61 (19) |
C3—C4—C5—C6 | −1.1 (3) | C22—C17—C18—C19 | 1.6 (3) |
O1—C1—C6—C5 | −179.12 (16) | C10—C17—C18—C19 | −175.59 (15) |
C2—C1—C6—C5 | 1.2 (3) | C17—C18—C19—C20 | −1.3 (3) |
O1—C1—C6—C7 | 3.0 (3) | C18—C19—C20—C21 | −0.6 (3) |
C2—C1—C6—C7 | −176.68 (16) | C18—C19—C20—C23 | 178.06 (19) |
C4—C5—C6—C1 | −0.1 (3) | C19—C20—C21—C22 | 2.2 (3) |
C4—C5—C6—C7 | 177.88 (17) | C23—C20—C21—C22 | −176.5 (2) |
C1—C6—C7—N1 | −125.26 (16) | C18—C17—C22—C21 | −0.1 (3) |
C5—C6—C7—N1 | 56.9 (2) | C10—C17—C22—C21 | 177.14 (17) |
C1—C6—C7—C8 | −6.1 (2) | C20—C21—C22—C17 | −1.8 (3) |
C5—C6—C7—C8 | 176.00 (15) | C9—C8—C24—O3 | −80.1 (3) |
N1—C7—C8—C24 | −134.90 (14) | C10—C8—C24—O3 | 41.9 (3) |
C6—C7—C8—C24 | 102.56 (16) | C7—C8—C24—O3 | 155.8 (2) |
N1—C7—C8—C9 | 101.55 (15) | C9—C8—C24—O4 | 99.69 (18) |
C6—C7—C8—C9 | −20.99 (18) | C10—C8—C24—O4 | −138.38 (16) |
N1—C7—C8—C10 | −14.50 (15) | C7—C8—C24—O4 | −24.4 (2) |
C6—C7—C8—C10 | −137.04 (14) | C16—C11—N1—O2 | −25.1 (2) |
C24—C8—C9—O1 | −72.08 (17) | C12—C11—N1—O2 | 161.65 (14) |
C10—C8—C9—O1 | 164.32 (13) | C16—C11—N1—C7 | −147.58 (15) |
C7—C8—C9—O1 | 53.43 (18) | C12—C11—N1—C7 | 39.2 (2) |
C24—C8—C10—O2 | 156.94 (13) | C6—C7—N1—C11 | −123.39 (15) |
C9—C8—C10—O2 | −81.01 (14) | C8—C7—N1—C11 | 112.79 (15) |
C7—C8—C10—O2 | 35.94 (14) | C6—C7—N1—O2 | 111.56 (14) |
C24—C8—C10—C17 | −84.50 (19) | C8—C7—N1—O2 | −12.26 (15) |
C9—C8—C10—C17 | 37.5 (2) | C6—C1—O1—C9 | 29.8 (2) |
C7—C8—C10—C17 | 154.50 (15) | C2—C1—O1—C9 | −150.52 (16) |
C16—C11—C12—C13 | −0.2 (3) | C8—C9—O1—C1 | −58.64 (19) |
N1—C11—C12—C13 | 173.12 (16) | C11—N1—O2—C10 | −92.54 (14) |
C11—C12—C13—C14 | −0.3 (3) | C7—N1—O2—C10 | 37.19 (14) |
C12—C13—C14—C15 | 0.8 (3) | C17—C10—O2—N1 | −172.31 (12) |
C13—C14—C15—C16 | −0.7 (3) | C8—C10—O2—N1 | −46.05 (13) |
C14—C15—C16—C11 | 0.1 (3) | O3—C24—O4—C25 | 0.6 (3) |
C12—C11—C16—C15 | 0.3 (3) | C8—C24—O4—C25 | −179.18 (19) |
N1—C11—C16—C15 | −173.06 (16) |
Cg3 and Cg5 are the centroids of rings C1–C6 and C17–C22, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg5i | 0.93 | 2.91 | 3.757 (2) | 151 |
C25—H25B···Cg3ii | 0.96 | 2.71 | 3.450 (3) | 134 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y−1, z. |
Cg3 and Cg5 are the centroids of rings C1–C6 and C17–C22, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg5i | 0.93 | 2.91 | 3.757 (2) | 151 |
C25—H25B···Cg3ii | 0.96 | 2.71 | 3.450 (3) | 134 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y−1, z. |
Acknowledgements
SA thanks the UGC, India, for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Isoxazoline derivatives have been shown to be efficient precursors for the preparation of many synthetic intermediates including γ-amino alcohols and β-hydroxy ketones (Kozikowski, 1984). They display interesting biological properties such as herbicidal, plant growth regulators and antitumour activities (Howe & Shelton, 1990). The title compound in which a chromane and isoxazole ring are fused was synthesized by (Bakthadoss & Murugan, 2010), and we report herein on its crystal structure.
The molecular structure of the title molecule is shown in Fig. 1. The bond lengths (Allen et al., 1987) and bond angles are normal. The pyran ring (O1/C1/C6-C9) of the chromane moiety adopts an envelope conformation with atom C9 as the flap; puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli,1983) are: q2=0.405 (2) Å, q3 = -0.247 (2) Å, φ2 = 123.9 (3)° and Δs(C9)= 6.26 (2)°, respectively.
The isoxazole ring (N1/C7/C8/C10/O2) has a twist conformation on bond O2-C10. The attached aromatic rings (C11—C16 and C17—C22) are twisted away from its mean plane by 56.19 (10)° and 50.57 (10)°, respectively. The two aromatic rings are normal to each other with a dihedral angle of 89.2 (1) °.
The carboxylate group assumes an extended conformation which can be seen from the torsion angle C8—C24—O4—C25 = -179.18 (19)°.
In the crystal, there are no classical hydrogen bonds. The molecules are linked via C—H···π interactions (Table 1), forming a two-dimensional network lying parallel to plane (1 0 -1).