organic compounds
[2-Benzyl-3-(naphthalen-1-yl)-2,3-dihydro-1,2-oxazole-4,5-diyl]bis(phenylmethanone)
aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com
In the title compound, C34H25NO3, the five-membered heterocyclic ring adopts an with the N atom as the flap. The plane through the four basal atoms of this ring makes dihedral angles of 69.78 (13), 53.15 (12) and 86.42 (13)°, respectively, with the benzene rings of the benzyl group and the two phenylmethanone groups at the 4 and 5 positions, and of 78.60 (11)° with the naphthalenyl system. In the crystal, the molecules are linked through C—H⋯O and C—H⋯π contacts into layers parallel to (101).
CCDC reference: 986600
Related literature
For background to isoxazoline dervatives and their applications, see: Gahlot et al. (2003); Kiss et al. (2009); Norman et al. (2007); Shi et al. (2012); Habeeb et al. (2001). For the synthesis of related compounds, see: Chakraborty et al. (2012). For a related structure, see: Sandhya et al. (2013). For ring puckering analysis, see: Cremer & Pople (1975).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); 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) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 986600
10.1107/S1600536814003250/yk2103sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003250/yk2103Isup2.hkl
The title compound was prepared by adapting a reported procedure (Chakraborty et al., 2012). N-naphthylidene-N-benzylnitrone, (3 mmol) and dibenzoylacetylene (3 mmol) were added into 15 mL of acetonitrile and stirred for 4 h at room temperature. The reaction was monitored by TLC using EtOAc/hexane (1:5). The solvent was removed under reduced pressure and the product was purified from the crude by
on silica gel. Colourless crystals suitable for X-ray were grown from ethanol by slow evaporation (m.p: 134 °C).All H atoms on C were placed in calculated positions, guided by difference maps, with C–H bond distances of 0.93–0.98 Å. H atoms were assigned Uiso=1.2Ueq(carrier) or 1.5Ueq (methyl C). Omitted owing to bad disagreement was the reflection (-1 0 1).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).Fig. 1. ORTEP view of the title compound drawn with 50% probability displacement ellipsoids for the non-H atoms. | |
Fig. 2. C—H···O intermolecular hydrogen bonding interactions found in the title compound. | |
Fig. 3. C—H···π interaction found in the title compound. | |
Fig. 4. C—H···O intermolecular hydrogen bonding connecting dimers into layers. | |
Fig. 5. Packing diagram of the compound along the a axis. |
C34H25NO3 | F(000) = 1040 |
Mr = 495.55 | Dx = 1.301 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3803 reflections |
a = 14.4105 (10) Å | θ = 2.3–27.8° |
b = 10.9408 (9) Å | µ = 0.08 mm−1 |
c = 16.0924 (13) Å | T = 296 K |
β = 94.235 (4)° | Block, colourless |
V = 2530.2 (3) Å3 | 0.40 × 0.35 × 0.30 mm |
Z = 4 |
Bruker Kappa APEXII CCD area-detector diffractometer | 5822 independent reflections |
Radiation source: fine-focus sealed tube | 3603 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and φ scan | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS, Bruker, 2007) | h = −16→18 |
Tmin = 0.968, Tmax = 0.976 | k = −6→14 |
12772 measured reflections | l = −19→20 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0908P)2 + 0.7195P] where P = (Fo2 + 2Fc2)/3 |
6092 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C34H25NO3 | V = 2530.2 (3) Å3 |
Mr = 495.55 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.4105 (10) Å | µ = 0.08 mm−1 |
b = 10.9408 (9) Å | T = 296 K |
c = 16.0924 (13) Å | 0.40 × 0.35 × 0.30 mm |
β = 94.235 (4)° |
Bruker Kappa APEXII CCD area-detector diffractometer | 5822 independent reflections |
Absorption correction: multi-scan (SADABS, Bruker, 2007) | 3603 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.976 | Rint = 0.028 |
12772 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.22 e Å−3 |
6092 reflections | Δρmin = −0.22 e Å−3 |
343 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.39550 (11) | 0.44858 (16) | 0.08868 (12) | 0.0624 (5) | |
O2 | 0.19673 (10) | 0.34089 (13) | 0.03919 (9) | 0.0432 (4) | |
O3 | 0.26338 (13) | 0.62696 (16) | 0.20136 (11) | 0.0630 (5) | |
N1 | 0.10514 (11) | 0.30910 (15) | 0.07285 (10) | 0.0390 (4) | |
C3 | 0.2856 (2) | 0.7599 (3) | −0.12462 (16) | 0.0723 (8) | |
H3 | 0.2782 | 0.8197 | −0.1656 | 0.087* | |
C4 | 0.3717 (2) | 0.7075 (3) | −0.10706 (16) | 0.0686 (8) | |
H4 | 0.4219 | 0.7315 | −0.1363 | 0.082* | |
C5 | 0.38332 (17) | 0.6192 (2) | −0.04588 (15) | 0.0537 (6) | |
H5 | 0.4416 | 0.5848 | −0.0331 | 0.064* | |
C6 | 0.30779 (14) | 0.58189 (18) | −0.00355 (13) | 0.0402 (5) | |
C7 | 0.32028 (14) | 0.48646 (19) | 0.06095 (13) | 0.0409 (5) | |
C8 | 0.23384 (13) | 0.42734 (18) | 0.09116 (12) | 0.0381 (4) | |
C9 | 0.19231 (13) | 0.44248 (18) | 0.16161 (12) | 0.0366 (4) | |
C17 | 0.11552 (13) | 0.34732 (18) | 0.16270 (12) | 0.0364 (4) | |
H17 | 0.1356 | 0.2781 | 0.1983 | 0.044* | |
C18 | 0.02157 (13) | 0.39606 (18) | 0.18652 (12) | 0.0384 (4) | |
C19 | −0.02994 (13) | 0.3363 (2) | 0.24645 (12) | 0.0398 (5) | |
C20 | −0.00101 (16) | 0.2282 (2) | 0.28950 (14) | 0.0478 (5) | |
H20 | 0.0561 | 0.1934 | 0.2798 | 0.057* | |
C21 | −0.05523 (18) | 0.1743 (3) | 0.34471 (15) | 0.0602 (6) | |
H21 | −0.0346 | 0.1035 | 0.3723 | 0.072* | |
C22 | −0.14162 (19) | 0.2239 (3) | 0.36060 (16) | 0.0702 (8) | |
H22 | −0.1784 | 0.1854 | 0.3979 | 0.084* | |
C1 | 0.22138 (16) | 0.6349 (2) | −0.02256 (15) | 0.0523 (6) | |
H1 | 0.1704 | 0.6096 | 0.0052 | 0.063* | |
C2 | 0.2108 (2) | 0.7250 (3) | −0.08236 (17) | 0.0677 (7) | |
H2 | 0.1532 | 0.7620 | −0.0940 | 0.081* | |
C28 | 0.09503 (15) | 0.17655 (19) | 0.06203 (13) | 0.0446 (5) | |
H28A | 0.0495 | 0.1464 | 0.0985 | 0.054* | |
H28B | 0.1540 | 0.1372 | 0.0779 | 0.054* | |
C29 | 0.06476 (14) | 0.14371 (18) | −0.02659 (12) | 0.0388 (5) | |
C34 | 0.11531 (16) | 0.0652 (2) | −0.07236 (15) | 0.0540 (6) | |
H34 | 0.1706 | 0.0321 | −0.0488 | 0.065* | |
C33 | 0.08423 (19) | 0.0350 (3) | −0.15369 (17) | 0.0665 (7) | |
H33 | 0.1192 | −0.0182 | −0.1839 | 0.080* | |
C32 | 0.0036 (2) | 0.0818 (3) | −0.18963 (16) | 0.0656 (7) | |
H32 | −0.0161 | 0.0619 | −0.2443 | 0.079* | |
C31 | −0.0483 (2) | 0.1589 (3) | −0.14438 (17) | 0.0718 (8) | |
H31 | −0.1041 | 0.1905 | −0.1680 | 0.086* | |
C30 | −0.01775 (18) | 0.1895 (2) | −0.06364 (16) | 0.0586 (6) | |
H30 | −0.0534 | 0.2419 | −0.0335 | 0.070* | |
C10 | 0.21642 (14) | 0.53967 (19) | 0.22180 (13) | 0.0413 (5) | |
C11 | 0.18224 (13) | 0.53279 (19) | 0.30646 (12) | 0.0388 (5) | |
C16 | 0.15152 (16) | 0.6376 (2) | 0.34411 (14) | 0.0511 (6) | |
H16 | 0.1521 | 0.7120 | 0.3161 | 0.061* | |
C15 | 0.12022 (18) | 0.6322 (3) | 0.42265 (16) | 0.0612 (7) | |
H15 | 0.0991 | 0.7026 | 0.4475 | 0.073* | |
C14 | 0.12018 (18) | 0.5226 (3) | 0.46435 (16) | 0.0630 (7) | |
H14 | 0.0988 | 0.5192 | 0.5174 | 0.076* | |
C13 | 0.15140 (19) | 0.4183 (3) | 0.42821 (15) | 0.0616 (7) | |
H13 | 0.1521 | 0.3446 | 0.4571 | 0.074* | |
C12 | 0.18182 (16) | 0.4228 (2) | 0.34900 (13) | 0.0481 (5) | |
H12 | 0.2021 | 0.3519 | 0.3241 | 0.058* | |
C23 | −0.17159 (18) | 0.3275 (3) | 0.32192 (16) | 0.0673 (8) | |
H23 | −0.2288 | 0.3603 | 0.3333 | 0.081* | |
C24 | −0.11730 (15) | 0.3873 (2) | 0.26426 (14) | 0.0497 (6) | |
C25 | −0.14949 (17) | 0.4948 (3) | 0.22237 (17) | 0.0617 (7) | |
H25 | −0.2066 | 0.5278 | 0.2339 | 0.074* | |
C26 | −0.09828 (18) | 0.5506 (2) | 0.16541 (17) | 0.0613 (7) | |
H26 | −0.1197 | 0.6217 | 0.1388 | 0.074* | |
C27 | −0.01301 (16) | 0.4992 (2) | 0.14757 (15) | 0.0495 (5) | |
H27 | 0.0213 | 0.5365 | 0.1079 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0422 (9) | 0.0586 (11) | 0.0866 (13) | 0.0009 (7) | 0.0058 (8) | 0.0176 (9) |
O2 | 0.0480 (8) | 0.0400 (8) | 0.0431 (8) | −0.0091 (6) | 0.0131 (6) | −0.0046 (6) |
O3 | 0.0778 (12) | 0.0517 (10) | 0.0607 (10) | −0.0289 (9) | 0.0140 (9) | −0.0076 (8) |
N1 | 0.0434 (9) | 0.0356 (9) | 0.0388 (9) | −0.0078 (7) | 0.0088 (7) | −0.0023 (7) |
C3 | 0.104 (2) | 0.0635 (18) | 0.0487 (14) | −0.0184 (16) | −0.0017 (14) | 0.0174 (13) |
C4 | 0.086 (2) | 0.0664 (18) | 0.0564 (16) | −0.0176 (15) | 0.0268 (14) | 0.0029 (13) |
C5 | 0.0564 (13) | 0.0514 (14) | 0.0556 (14) | −0.0056 (11) | 0.0204 (11) | −0.0035 (11) |
C6 | 0.0467 (11) | 0.0341 (11) | 0.0405 (11) | −0.0041 (8) | 0.0083 (9) | −0.0034 (9) |
C7 | 0.0389 (10) | 0.0365 (11) | 0.0485 (12) | −0.0032 (8) | 0.0111 (9) | −0.0024 (9) |
C8 | 0.0386 (10) | 0.0314 (10) | 0.0442 (11) | −0.0030 (8) | 0.0037 (8) | 0.0012 (8) |
C9 | 0.0358 (10) | 0.0336 (10) | 0.0404 (10) | −0.0049 (8) | 0.0035 (8) | −0.0021 (8) |
C17 | 0.0396 (10) | 0.0331 (10) | 0.0369 (10) | −0.0041 (8) | 0.0040 (8) | −0.0008 (8) |
C18 | 0.0389 (10) | 0.0355 (11) | 0.0404 (11) | −0.0026 (8) | −0.0001 (8) | −0.0042 (9) |
C19 | 0.0402 (10) | 0.0440 (12) | 0.0350 (10) | −0.0045 (9) | 0.0024 (8) | −0.0094 (9) |
C20 | 0.0496 (12) | 0.0472 (13) | 0.0465 (12) | −0.0027 (10) | 0.0033 (10) | 0.0005 (10) |
C21 | 0.0656 (15) | 0.0671 (17) | 0.0486 (13) | −0.0081 (13) | 0.0085 (12) | 0.0088 (12) |
C22 | 0.0658 (17) | 0.098 (2) | 0.0493 (15) | −0.0126 (15) | 0.0192 (13) | 0.0066 (15) |
C1 | 0.0514 (13) | 0.0501 (14) | 0.0553 (13) | −0.0036 (10) | 0.0037 (10) | 0.0066 (11) |
C2 | 0.0729 (17) | 0.0639 (18) | 0.0640 (16) | −0.0023 (13) | −0.0105 (13) | 0.0147 (13) |
C28 | 0.0518 (12) | 0.0354 (11) | 0.0465 (12) | −0.0080 (9) | 0.0027 (9) | 0.0000 (9) |
C29 | 0.0430 (11) | 0.0315 (10) | 0.0422 (11) | −0.0090 (8) | 0.0054 (9) | 0.0015 (8) |
C34 | 0.0439 (12) | 0.0585 (15) | 0.0599 (14) | −0.0020 (10) | 0.0050 (10) | −0.0097 (12) |
C33 | 0.0683 (17) | 0.0738 (19) | 0.0587 (15) | −0.0083 (14) | 0.0132 (13) | −0.0241 (14) |
C32 | 0.0844 (19) | 0.0665 (18) | 0.0447 (13) | −0.0212 (15) | −0.0026 (13) | −0.0066 (13) |
C31 | 0.0698 (17) | 0.073 (2) | 0.0683 (17) | 0.0023 (14) | −0.0215 (14) | 0.0094 (15) |
C30 | 0.0627 (15) | 0.0543 (15) | 0.0584 (15) | 0.0121 (12) | 0.0015 (12) | −0.0016 (12) |
C10 | 0.0419 (11) | 0.0340 (11) | 0.0475 (12) | −0.0049 (8) | 0.0011 (9) | −0.0014 (9) |
C11 | 0.0394 (10) | 0.0360 (11) | 0.0402 (11) | −0.0039 (8) | −0.0030 (8) | −0.0035 (8) |
C16 | 0.0616 (14) | 0.0389 (12) | 0.0522 (13) | 0.0008 (10) | −0.0001 (11) | −0.0040 (10) |
C15 | 0.0645 (15) | 0.0602 (17) | 0.0593 (15) | 0.0035 (12) | 0.0077 (12) | −0.0161 (13) |
C14 | 0.0679 (16) | 0.0777 (19) | 0.0441 (13) | −0.0106 (14) | 0.0084 (11) | −0.0074 (13) |
C13 | 0.0794 (17) | 0.0563 (16) | 0.0475 (14) | −0.0108 (13) | −0.0069 (12) | 0.0084 (12) |
C12 | 0.0613 (14) | 0.0392 (12) | 0.0425 (12) | −0.0001 (10) | −0.0035 (10) | −0.0020 (9) |
C23 | 0.0542 (14) | 0.095 (2) | 0.0547 (15) | 0.0045 (14) | 0.0191 (12) | −0.0079 (15) |
C24 | 0.0451 (12) | 0.0604 (15) | 0.0439 (12) | 0.0026 (10) | 0.0055 (9) | −0.0119 (11) |
C25 | 0.0494 (13) | 0.0660 (17) | 0.0698 (16) | 0.0146 (12) | 0.0064 (12) | −0.0136 (14) |
C26 | 0.0595 (15) | 0.0477 (15) | 0.0758 (17) | 0.0142 (11) | −0.0016 (13) | 0.0008 (13) |
C27 | 0.0504 (12) | 0.0413 (12) | 0.0566 (13) | 0.0013 (10) | 0.0019 (10) | 0.0037 (10) |
O1—C7 | 1.214 (3) | C28—C29 | 1.504 (3) |
O2—C8 | 1.347 (2) | C28—H28A | 0.9700 |
O2—N1 | 1.504 (2) | C28—H28B | 0.9700 |
O3—C10 | 1.229 (2) | C29—C34 | 1.375 (3) |
N1—C28 | 1.467 (3) | C29—C30 | 1.384 (3) |
N1—C17 | 1.502 (2) | C34—C33 | 1.392 (3) |
C3—C2 | 1.371 (4) | C34—H34 | 0.9300 |
C3—C4 | 1.376 (4) | C33—C32 | 1.359 (4) |
C3—H3 | 0.9300 | C33—H33 | 0.9300 |
C4—C5 | 1.381 (4) | C32—C31 | 1.372 (4) |
C4—H4 | 0.9300 | C32—H32 | 0.9300 |
C5—C6 | 1.387 (3) | C31—C30 | 1.382 (4) |
C5—H5 | 0.9300 | C31—H31 | 0.9300 |
C6—C1 | 1.387 (3) | C30—H30 | 0.9300 |
C6—C7 | 1.474 (3) | C10—C11 | 1.484 (3) |
C7—C8 | 1.515 (3) | C11—C12 | 1.385 (3) |
C8—C9 | 1.331 (3) | C11—C16 | 1.385 (3) |
C9—C10 | 1.463 (3) | C16—C15 | 1.374 (3) |
C9—C17 | 1.520 (3) | C16—H16 | 0.9300 |
C17—C18 | 1.530 (3) | C15—C14 | 1.374 (4) |
C17—H17 | 0.9800 | C15—H15 | 0.9300 |
C18—C27 | 1.367 (3) | C14—C13 | 1.372 (4) |
C18—C19 | 1.419 (3) | C14—H14 | 0.9300 |
C19—C20 | 1.418 (3) | C13—C12 | 1.379 (3) |
C19—C24 | 1.425 (3) | C13—H13 | 0.9300 |
C20—C21 | 1.360 (3) | C12—H12 | 0.9300 |
C20—H20 | 0.9300 | C23—C24 | 1.417 (4) |
C21—C22 | 1.399 (4) | C23—H23 | 0.9300 |
C21—H21 | 0.9300 | C24—C25 | 1.416 (4) |
C22—C23 | 1.349 (4) | C25—C26 | 1.363 (4) |
C22—H22 | 0.9300 | C25—H25 | 0.9300 |
C1—C2 | 1.378 (3) | C26—C27 | 1.400 (3) |
C1—H1 | 0.9300 | C26—H26 | 0.9300 |
C2—H2 | 0.9300 | C27—H27 | 0.9300 |
C8—O2—N1 | 104.92 (13) | C29—C28—H28B | 109.3 |
C28—N1—C17 | 113.05 (16) | H28A—C28—H28B | 108.0 |
C28—N1—O2 | 105.55 (14) | C34—C29—C30 | 117.9 (2) |
C17—N1—O2 | 104.76 (13) | C34—C29—C28 | 122.0 (2) |
C2—C3—C4 | 120.8 (3) | C30—C29—C28 | 120.1 (2) |
C2—C3—H3 | 119.6 | C29—C34—C33 | 120.4 (2) |
C4—C3—H3 | 119.6 | C29—C34—H34 | 119.8 |
C3—C4—C5 | 119.9 (2) | C33—C34—H34 | 119.8 |
C3—C4—H4 | 120.1 | C32—C33—C34 | 121.1 (3) |
C5—C4—H4 | 120.1 | C32—C33—H33 | 119.5 |
C4—C5—C6 | 119.8 (2) | C34—C33—H33 | 119.5 |
C4—C5—H5 | 120.1 | C33—C32—C31 | 119.2 (2) |
C6—C5—H5 | 120.1 | C33—C32—H32 | 120.4 |
C5—C6—C1 | 119.5 (2) | C31—C32—H32 | 120.4 |
C5—C6—C7 | 119.6 (2) | C32—C31—C30 | 120.0 (3) |
C1—C6—C7 | 120.83 (19) | C32—C31—H31 | 120.0 |
O1—C7—C6 | 124.05 (19) | C30—C31—H31 | 120.0 |
O1—C7—C8 | 117.97 (19) | C31—C30—C29 | 121.4 (2) |
C6—C7—C8 | 117.89 (17) | C31—C30—H30 | 119.3 |
C9—C8—O2 | 115.69 (17) | C29—C30—H30 | 119.3 |
C9—C8—C7 | 130.71 (18) | O3—C10—C9 | 119.74 (19) |
O2—C8—C7 | 113.49 (16) | O3—C10—C11 | 120.77 (19) |
C8—C9—C10 | 123.70 (18) | C9—C10—C11 | 119.48 (17) |
C8—C9—C17 | 107.34 (17) | C12—C11—C16 | 119.3 (2) |
C10—C9—C17 | 128.87 (17) | C12—C11—C10 | 120.78 (19) |
N1—C17—C9 | 101.55 (15) | C16—C11—C10 | 119.87 (19) |
N1—C17—C18 | 108.13 (15) | C15—C16—C11 | 120.3 (2) |
C9—C17—C18 | 114.99 (16) | C15—C16—H16 | 119.9 |
N1—C17—H17 | 110.6 | C11—C16—H16 | 119.9 |
C9—C17—H17 | 110.6 | C14—C15—C16 | 119.9 (2) |
C18—C17—H17 | 110.6 | C14—C15—H15 | 120.0 |
C27—C18—C19 | 120.04 (19) | C16—C15—H15 | 120.0 |
C27—C18—C17 | 118.18 (18) | C13—C14—C15 | 120.5 (2) |
C19—C18—C17 | 121.78 (18) | C13—C14—H14 | 119.8 |
C20—C19—C18 | 124.51 (19) | C15—C14—H14 | 119.8 |
C20—C19—C24 | 117.42 (19) | C14—C13—C12 | 119.9 (2) |
C18—C19—C24 | 118.1 (2) | C14—C13—H13 | 120.0 |
C21—C20—C19 | 121.2 (2) | C12—C13—H13 | 120.0 |
C21—C20—H20 | 119.4 | C13—C12—C11 | 120.1 (2) |
C19—C20—H20 | 119.4 | C13—C12—H12 | 120.0 |
C20—C21—C22 | 120.9 (3) | C11—C12—H12 | 120.0 |
C20—C21—H21 | 119.6 | C22—C23—C24 | 121.1 (2) |
C22—C21—H21 | 119.6 | C22—C23—H23 | 119.4 |
C23—C22—C21 | 120.1 (2) | C24—C23—H23 | 119.4 |
C23—C22—H22 | 120.0 | C25—C24—C23 | 121.2 (2) |
C21—C22—H22 | 120.0 | C25—C24—C19 | 119.5 (2) |
C2—C1—C6 | 120.3 (2) | C23—C24—C19 | 119.3 (2) |
C2—C1—H1 | 119.9 | C26—C25—C24 | 121.2 (2) |
C6—C1—H1 | 119.9 | C26—C25—H25 | 119.4 |
C3—C2—C1 | 119.7 (3) | C24—C25—H25 | 119.4 |
C3—C2—H2 | 120.2 | C25—C26—C27 | 119.0 (2) |
C1—C2—H2 | 120.2 | C25—C26—H26 | 120.5 |
N1—C28—C29 | 111.61 (17) | C27—C26—H26 | 120.5 |
N1—C28—H28A | 109.3 | C18—C27—C26 | 122.2 (2) |
C29—C28—H28A | 109.3 | C18—C27—H27 | 118.9 |
N1—C28—H28B | 109.3 | C26—C27—H27 | 118.9 |
C8—O2—N1—C28 | −141.69 (16) | C6—C1—C2—C3 | 1.7 (4) |
C8—O2—N1—C17 | −22.12 (18) | C17—N1—C28—C29 | 167.93 (16) |
C2—C3—C4—C5 | −0.4 (4) | O2—N1—C28—C29 | −78.14 (19) |
C3—C4—C5—C6 | 1.3 (4) | N1—C28—C29—C34 | 123.4 (2) |
C4—C5—C6—C1 | −0.7 (3) | N1—C28—C29—C30 | −58.8 (3) |
C4—C5—C6—C7 | 179.2 (2) | C30—C29—C34—C33 | 0.9 (4) |
C5—C6—C7—O1 | 10.7 (3) | C28—C29—C34—C33 | 178.7 (2) |
C1—C6—C7—O1 | −169.4 (2) | C29—C34—C33—C32 | −0.1 (4) |
C5—C6—C7—C8 | −165.92 (19) | C34—C33—C32—C31 | −0.9 (4) |
C1—C6—C7—C8 | 14.0 (3) | C33—C32—C31—C30 | 1.0 (4) |
N1—O2—C8—C9 | 12.1 (2) | C32—C31—C30—C29 | −0.2 (4) |
N1—O2—C8—C7 | −171.20 (15) | C34—C29—C30—C31 | −0.8 (4) |
O1—C7—C8—C9 | 78.7 (3) | C28—C29—C30—C31 | −178.7 (2) |
C6—C7—C8—C9 | −104.5 (3) | C8—C9—C10—O3 | 15.1 (3) |
O1—C7—C8—O2 | −97.4 (2) | C17—C9—C10—O3 | −161.0 (2) |
C6—C7—C8—O2 | 79.4 (2) | C8—C9—C10—C11 | −166.10 (19) |
O2—C8—C9—C10 | −173.65 (18) | C17—C9—C10—C11 | 17.8 (3) |
C7—C8—C9—C10 | 10.3 (3) | O3—C10—C11—C12 | −140.3 (2) |
O2—C8—C9—C17 | 3.2 (2) | C9—C10—C11—C12 | 40.9 (3) |
C7—C8—C9—C17 | −172.8 (2) | O3—C10—C11—C16 | 38.8 (3) |
C28—N1—C17—C9 | 137.38 (16) | C9—C10—C11—C16 | −140.0 (2) |
O2—N1—C17—C9 | 22.96 (18) | C12—C11—C16—C15 | −0.5 (3) |
C28—N1—C17—C18 | −101.25 (19) | C10—C11—C16—C15 | −179.7 (2) |
O2—N1—C17—C18 | 144.34 (15) | C11—C16—C15—C14 | 0.6 (4) |
C8—C9—C17—N1 | −16.8 (2) | C16—C15—C14—C13 | 0.1 (4) |
C10—C9—C17—N1 | 159.83 (19) | C15—C14—C13—C12 | −0.9 (4) |
C8—C9—C17—C18 | −133.25 (18) | C14—C13—C12—C11 | 1.0 (4) |
C10—C9—C17—C18 | 43.4 (3) | C16—C11—C12—C13 | −0.3 (3) |
N1—C17—C18—C27 | −64.1 (2) | C10—C11—C12—C13 | 178.8 (2) |
C9—C17—C18—C27 | 48.5 (3) | C21—C22—C23—C24 | 0.6 (4) |
N1—C17—C18—C19 | 115.07 (19) | C22—C23—C24—C25 | 178.7 (3) |
C9—C17—C18—C19 | −132.28 (19) | C22—C23—C24—C19 | 0.5 (4) |
C27—C18—C19—C20 | 179.1 (2) | C20—C19—C24—C25 | −179.5 (2) |
C17—C18—C19—C20 | −0.1 (3) | C18—C19—C24—C25 | −0.2 (3) |
C27—C18—C19—C24 | −0.2 (3) | C20—C19—C24—C23 | −1.3 (3) |
C17—C18—C19—C24 | −179.36 (18) | C18—C19—C24—C23 | 178.1 (2) |
C18—C19—C20—C21 | −178.4 (2) | C23—C24—C25—C26 | −178.4 (2) |
C24—C19—C20—C21 | 0.9 (3) | C19—C24—C25—C26 | −0.2 (4) |
C19—C20—C21—C22 | 0.2 (4) | C24—C25—C26—C27 | 0.9 (4) |
C20—C21—C22—C23 | −1.0 (4) | C19—C18—C27—C26 | 0.9 (3) |
C5—C6—C1—C2 | −0.8 (3) | C17—C18—C27—C26 | −179.9 (2) |
C7—C6—C1—C2 | 179.3 (2) | C25—C26—C27—C18 | −1.3 (4) |
C4—C3—C2—C1 | −1.1 (4) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.60 | 3.392 (3) | 144 |
C12—H12···O3ii | 0.93 | 2.55 | 3.443 (3) | 161 |
C13—H13···Cg1ii | 0.93 | 2.63 | 3.523 (3) | 161 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y−1/2, −z+1/2. |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.9300 | 2.60 | 3.392 (3) | 144 |
C12—H12···O3ii | 0.9300 | 2.55 | 3.443 (3) | 161 |
C13—H13···Cg1ii | 0.93 | 2.63 | 3.523 (3) | 161 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
RS is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of a Senior Research Fellowship. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India for single-crystal X-ray diffraction measurements.
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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 exhibit a wide spectrum of biological activities such as anti-microbial (Gahlot et al., 2003), anti-diabetic (Norman et al., 2007), anti-cancer (Shi et al., 2012) and anti-inflammatory activities (Habeeb et al., 2001). Besides of their pharmacological properties, isoxazolines are also used as intermediates in organic synthesis (Kiss et al., 2009). Herein we report the structure of an isoxazoline derivative synthesized by the 1,3-dipolar cycloaddition reaction of N-naphthylidene-N-benzylnitrone with dibenzoylacetylene. As a continuous work (Sandhya et al., 2013) on the isoxazoline derivatives, a new compound, (2-benzyl-3-(naphthalen-1-yl)-2,3-dihydroisoxazole-4,5-diyl)bis(phenylmethanone), was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.
The compound crystallizes in the monoclinic space group P21/n. The dihedral angles between the three aromatic six-membered rings of the benzophenyl (C1–C6 and C11–C16) and benzyl (C29–C34) moieties attached to the heterocyclic ring are 80.27 (12), 60.20 (11) and 63.96 (12)° respectively. The five-membered heterocyclic ring C8/C9/C17/O2/N1 is in an envelope conformation on N1 [φ = 3.9 (3)°] (Cremer & Pople, 1975).
There are two intermolecular C–H···O hydrogen bond interactions (Fig. 2) between the H atoms attached at the C5 & C12 and O1 & O3 atoms of the neighbouring molecule with D···A distances of 3.392 (3) and 3.443 (3) Å respectively. One of the above interaction (C5–H5···O1) forms a centerosymmetric dimer with the adjacent molecule while the other connects such dimers together to build a molecular chain (Fig. 3) in the lattice. An intermolecular C–H···π interaction (Fig. 4) between the H at C13 and the C1-C6 aromatic ring of the neighbouring molecule with H···π distance of 2.63 Å interconnects the molecular chains together. Thus, these intermolecular hydrogen bonding interactions augmented by a C–H···π interaction play a major role to form a supramolecular network in the lattice of the molecular system. Similar intermolecular interactions are found in the compound (2-tert-butyl-3-phenyl-2,3-dihydroisoxazole-4,5-diyl)bis(phenylmethanone) (Sandhya et al., 2013). Fig. 5 shows the packing diagram of the title compound along a axis.