organic compounds
16-Oxapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18-heptaen-15-one
aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com
In the title compound, C18H12O2, the benzene rings are inclined to one another by 66.79 (7)°. The five-membered ring is almost planar with a maximum deviation of 0.014 (1) Å. In the crystal, the molecules are linked by pairs of weak C—H⋯O interactions into centrosymmetric dimers. These dimers are linked by C—H⋯π interactions, forming a three-dimensional structure.
CCDC reference: 979286
Related literature
For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010); Cox et al. (2013). For the synthesis of related compounds, see: Ciganek (1980); De Luca et al. (2001). For a related structure, see: Mathew et al. (2013). For 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: 979286
10.1107/S1600536814000026/yk2102sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000026/yk2102Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000026/yk2102Isup3.cml
The title compound was prepared by adapting a reported procedure (Ciganek, 1980; De Luca et al., 2001). Triethylamine (0.70 ml, 5 mmol) was added to a solution of 9-anthracene carboxylic acid (1.11 g, 5 mmol) and cyanuric chloride (0.92 g, 5 mmol) in acetone and stirred at room temperature for 1 h to obtain 9-anthracene acid chloride. Propargyl alcohol (0.30 ml, 5 mmol) was added to it and the mixture was stirred for 4 h. Propargyl-9-anthroate obtained was purified by silica gel
using a mixture of hexane and dichloromethane as eluents. Propargyl-9-anthroate was refluxed in 10 ml of p-xylene for 48 h (intramolecular Diels-Alder reaction) to generate the title compound. Colourless crystals acceptable for X-ray were recrystallized from acetonitrile by slow evaporation over a few days (m.p: 260 °C).All H atoms on C were placed in calculated positions, guided by difference maps, with C–H bond distances 0.93–0.97 Å. H atoms were assigned as Uiso=1.2Ueq. Omitted owing to bad disagreement were the reflections (1 0 0).
Dibenzobarrelene derivatives have been used as the key intermediates in the synthesis of several compounds which show various biological activities. Besides, they have showed application in drug development for various diseases (Khalil et al., 2010) and in the alignment of nematic liquid crystals (Cox et al., 2013). As a continuous work on the dibenzobarrelene compounds, a new dibenzobarrelene derivative, 3,5-dihydro-5,9 b-o-benzonaphtho [1,2-c] furan-1-one, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.
The compound crystallizes in monoclinic φ = 117.52 (10)° and θ = 90.62 (10)°] having total puckering amplitude QT of 0.8495 (15) Å. The other six-membered ring C5—C7/C14/C17/C18 is also in boat conformation [φ = 302.45 (11)° and θ = 89.63 (12)°] having total puckering amplitude QT of 0.7919 (15) Å. Another six-membered ring C7/C8/C13/C14/C17/C18 is also in the same conformation [φ = 181.09 (11)° and θ = 90.35 (11)°] having total puckering amplitude QT of 0.7915 (15) Å (Cremer & Pople, 1975).
P21/c. The dihedral angle of the two aromatic rings of the anthracene moiety is 66.79 (7)°. The five-membered heterocyclic ring C14–17/O2 is almost planar with a maximum deviation of 0.014 (1)° for C14 carbon atom in the ring. One of the fused six-membered ring of the molecule C5—C8/C13/C14 is in boat conformation [Three C–H···π interactions (Fig. 2) are found in the molecule. Whilst the two C–H···π interactions exist between the H atoms attached at the C7 and C16 atoms and the aromatic rings (C1—C6) of the anthracene moiety of two adjacent molecules from opposite sides of the main molecule, the third C–H···π interaction exists between the hydrogen at C18 atom and the C8—C13 ring of one of the above neighbouring molecules respectively with H···π distances of 2.92, 2.76 and 2.84 Å (Table 1). There are very weak π···π interactions between the aromatic rings of the anthracene moiety with centroid-centroid distances greater than 4 Å. However, packing of molecules is predominantly favored by the C–H···π interactions. Similar intermolecular interactive behaviour was found in the compound 8-phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18- heptane (Mathew et al., 2013). Fig. 3 shows the packing diagram of the title compound along a axis.
For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010); Cox et al. (2013). For the synthesis of related compounds, see: Ciganek (1980); De Luca et al. (2001). For related structure, see: Mathew et al. (2013). For puckering analysis, see: Cremer & Pople (1975).
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 molecule drawn with 50% probability displacement ellipsoids and showing the atom labelling scheme. | |
Fig. 2. C—H···π interactions in the title compound. | |
Fig. 3. Packing diagram of the compound along a axis. |
C18H12O2 | F(000) = 544 |
Mr = 260.28 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2538 reflections |
a = 9.351 (1) Å | θ = 2.7–27.2° |
b = 13.8153 (16) Å | µ = 0.09 mm−1 |
c = 10.1514 (9) Å | T = 296 K |
β = 105.295 (4)° | Block, colourless |
V = 1265.0 (2) Å3 | 0.40 × 0.35 × 0.30 mm |
Z = 4 |
Bruker Kappa APEXII CCD area-detector diffractometer | 3123 independent reflections |
Radiation source: fine-focus sealed tube | 2224 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.7° |
ω and φ scan | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | k = −18→18 |
Tmin = 0.966, Tmax = 0.974 | l = −9→13 |
9570 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0716P)2 + 0.0884P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3123 reflections | Δρmax = 0.22 e Å−3 |
182 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.042 (4) |
C18H12O2 | V = 1265.0 (2) Å3 |
Mr = 260.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.351 (1) Å | µ = 0.09 mm−1 |
b = 13.8153 (16) Å | T = 296 K |
c = 10.1514 (9) Å | 0.40 × 0.35 × 0.30 mm |
β = 105.295 (4)° |
Bruker Kappa APEXII CCD area-detector diffractometer | 3123 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2224 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.974 | Rint = 0.035 |
9570 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
3123 reflections | Δρmin = −0.19 e Å−3 |
182 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 | ||
O1 | 0.80024 (14) | −0.01503 (9) | 0.22190 (12) | 0.0570 (4) | |
O2 | 0.81229 (15) | −0.05665 (8) | 0.43556 (13) | 0.0590 (4) | |
C1 | 0.35542 (16) | 0.23405 (12) | 0.28342 (15) | 0.0410 (4) | |
H1 | 0.3188 | 0.2869 | 0.3209 | 0.049* | |
C2 | 0.27224 (16) | 0.19194 (12) | 0.16350 (15) | 0.0454 (4) | |
H2 | 0.1799 | 0.2175 | 0.1198 | 0.054* | |
C3 | 0.32484 (18) | 0.11291 (12) | 0.10856 (15) | 0.0440 (4) | |
H3 | 0.2663 | 0.0840 | 0.0300 | 0.053* | |
C4 | 0.46477 (17) | 0.07589 (11) | 0.16959 (13) | 0.0368 (3) | |
H4 | 0.5010 | 0.0230 | 0.1318 | 0.044* | |
C5 | 0.54912 (15) | 0.11890 (10) | 0.28707 (13) | 0.0294 (3) | |
C6 | 0.49305 (15) | 0.19640 (10) | 0.34614 (13) | 0.0323 (3) | |
C7 | 0.59990 (16) | 0.23295 (11) | 0.47731 (13) | 0.0372 (4) | |
H7 | 0.5584 | 0.2858 | 0.5201 | 0.045* | |
C8 | 0.73588 (15) | 0.26293 (10) | 0.43345 (13) | 0.0329 (3) | |
C9 | 0.79945 (18) | 0.35413 (11) | 0.44610 (15) | 0.0426 (4) | |
H9 | 0.7627 | 0.4033 | 0.4905 | 0.051* | |
C10 | 0.91836 (18) | 0.37120 (12) | 0.39195 (16) | 0.0472 (4) | |
H10 | 0.9615 | 0.4323 | 0.4001 | 0.057* | |
C11 | 0.97316 (17) | 0.29906 (12) | 0.32652 (16) | 0.0462 (4) | |
H11 | 1.0519 | 0.3120 | 0.2893 | 0.055* | |
C12 | 0.91213 (15) | 0.20649 (11) | 0.31525 (14) | 0.0373 (3) | |
H12 | 0.9503 | 0.1573 | 0.2720 | 0.045* | |
C13 | 0.79444 (14) | 0.18928 (10) | 0.36931 (12) | 0.0297 (3) | |
C14 | 0.70748 (15) | 0.09493 (10) | 0.36761 (13) | 0.0298 (3) | |
C15 | 0.77607 (17) | 0.00483 (11) | 0.32910 (16) | 0.0408 (4) | |
C16 | 0.7720 (2) | −0.01959 (13) | 0.55478 (17) | 0.0566 (5) | |
H16A | 0.8592 | −0.0126 | 0.6311 | 0.068* | |
H16B | 0.7028 | −0.0629 | 0.5813 | 0.068* | |
C17 | 0.70234 (16) | 0.07596 (12) | 0.51340 (14) | 0.0375 (3) | |
C18 | 0.64493 (17) | 0.14591 (12) | 0.57090 (14) | 0.0419 (4) | |
H18 | 0.6331 | 0.1426 | 0.6589 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0749 (9) | 0.0426 (7) | 0.0586 (7) | 0.0140 (6) | 0.0266 (6) | −0.0097 (6) |
O2 | 0.0767 (9) | 0.0353 (7) | 0.0645 (8) | 0.0168 (6) | 0.0177 (6) | 0.0126 (6) |
C1 | 0.0341 (8) | 0.0432 (9) | 0.0454 (8) | 0.0049 (6) | 0.0097 (6) | −0.0012 (7) |
C2 | 0.0322 (8) | 0.0528 (10) | 0.0457 (8) | −0.0005 (7) | 0.0005 (7) | 0.0072 (7) |
C3 | 0.0429 (8) | 0.0487 (10) | 0.0339 (7) | −0.0133 (7) | −0.0015 (6) | 0.0007 (7) |
C4 | 0.0452 (8) | 0.0319 (7) | 0.0332 (7) | −0.0058 (6) | 0.0099 (6) | −0.0028 (6) |
C5 | 0.0327 (7) | 0.0288 (7) | 0.0268 (6) | −0.0021 (5) | 0.0079 (5) | 0.0025 (5) |
C6 | 0.0311 (7) | 0.0355 (8) | 0.0304 (6) | −0.0006 (5) | 0.0085 (5) | 0.0000 (6) |
C7 | 0.0383 (8) | 0.0412 (8) | 0.0311 (7) | 0.0048 (6) | 0.0076 (6) | −0.0096 (6) |
C8 | 0.0330 (7) | 0.0337 (7) | 0.0276 (6) | 0.0023 (6) | 0.0003 (5) | −0.0045 (5) |
C9 | 0.0451 (9) | 0.0339 (8) | 0.0396 (8) | 0.0026 (6) | −0.0049 (7) | −0.0080 (6) |
C10 | 0.0407 (9) | 0.0386 (9) | 0.0532 (9) | −0.0103 (7) | −0.0035 (7) | 0.0001 (7) |
C11 | 0.0296 (7) | 0.0513 (10) | 0.0542 (9) | −0.0062 (6) | 0.0051 (7) | 0.0080 (8) |
C12 | 0.0292 (7) | 0.0400 (8) | 0.0417 (7) | 0.0033 (6) | 0.0073 (6) | 0.0026 (6) |
C13 | 0.0295 (7) | 0.0289 (7) | 0.0279 (6) | 0.0029 (5) | 0.0026 (5) | 0.0007 (5) |
C14 | 0.0337 (7) | 0.0271 (7) | 0.0286 (6) | 0.0017 (5) | 0.0080 (5) | 0.0002 (5) |
C15 | 0.0437 (8) | 0.0306 (8) | 0.0477 (8) | 0.0037 (6) | 0.0111 (7) | −0.0007 (7) |
C16 | 0.0646 (11) | 0.0535 (11) | 0.0507 (9) | 0.0097 (9) | 0.0136 (9) | 0.0200 (8) |
C17 | 0.0371 (8) | 0.0429 (8) | 0.0307 (7) | 0.0001 (6) | 0.0056 (6) | 0.0074 (6) |
C18 | 0.0426 (8) | 0.0582 (10) | 0.0251 (6) | −0.0012 (7) | 0.0092 (6) | 0.0013 (6) |
O1—C15 | 1.2001 (19) | C8—C9 | 1.385 (2) |
O2—C15 | 1.3457 (19) | C8—C13 | 1.3955 (19) |
O2—C16 | 1.452 (2) | C9—C10 | 1.384 (2) |
C1—C6 | 1.3783 (19) | C9—H9 | 0.9300 |
C1—C2 | 1.388 (2) | C10—C11 | 1.370 (2) |
C1—H1 | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.375 (2) | C11—C12 | 1.393 (2) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.389 (2) | C12—C13 | 1.374 (2) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.3788 (19) | C13—C14 | 1.5339 (19) |
C4—H4 | 0.9300 | C14—C15 | 1.499 (2) |
C5—C6 | 1.395 (2) | C14—C17 | 1.5163 (18) |
C5—C14 | 1.5272 (18) | C16—C17 | 1.483 (2) |
C6—C7 | 1.5246 (18) | C16—H16A | 0.9700 |
C7—C8 | 1.512 (2) | C16—H16B | 0.9700 |
C7—C18 | 1.521 (2) | C17—C18 | 1.315 (2) |
C7—H7 | 0.9800 | C18—H18 | 0.9300 |
C15—O2—C16 | 112.40 (12) | C11—C10—H10 | 119.6 |
C6—C1—C2 | 119.08 (15) | C9—C10—H10 | 119.6 |
C6—C1—H1 | 120.5 | C10—C11—C12 | 120.68 (15) |
C2—C1—H1 | 120.5 | C10—C11—H11 | 119.7 |
C3—C2—C1 | 120.74 (14) | C12—C11—H11 | 119.7 |
C3—C2—H2 | 119.6 | C13—C12—C11 | 118.69 (14) |
C1—C2—H2 | 119.6 | C13—C12—H12 | 120.7 |
C2—C3—C4 | 120.47 (13) | C11—C12—H12 | 120.7 |
C2—C3—H3 | 119.8 | C12—C13—C8 | 120.96 (13) |
C4—C3—H3 | 119.8 | C12—C13—C14 | 128.37 (12) |
C5—C4—C3 | 118.93 (14) | C8—C13—C14 | 110.66 (12) |
C5—C4—H4 | 120.5 | C15—C14—C17 | 103.71 (12) |
C3—C4—H4 | 120.5 | C15—C14—C5 | 117.50 (11) |
C4—C5—C6 | 120.55 (13) | C17—C14—C5 | 106.50 (11) |
C4—C5—C14 | 128.48 (13) | C15—C14—C13 | 116.53 (12) |
C6—C5—C14 | 110.95 (11) | C17—C14—C13 | 106.81 (11) |
C1—C6—C5 | 120.13 (13) | C5—C14—C13 | 104.96 (10) |
C1—C6—C7 | 126.55 (14) | O1—C15—O2 | 121.07 (14) |
C5—C6—C7 | 113.29 (11) | O1—C15—C14 | 128.49 (14) |
C8—C7—C18 | 106.55 (12) | O2—C15—C14 | 110.44 (13) |
C8—C7—C6 | 104.00 (11) | O2—C16—C17 | 105.60 (12) |
C18—C7—C6 | 107.06 (12) | O2—C16—H16A | 110.6 |
C8—C7—H7 | 112.9 | C17—C16—H16A | 110.6 |
C18—C7—H7 | 112.9 | O2—C16—H16B | 110.6 |
C6—C7—H7 | 112.9 | C17—C16—H16B | 110.6 |
C9—C8—C13 | 119.68 (14) | H16A—C16—H16B | 108.8 |
C9—C8—C7 | 126.58 (14) | C18—C17—C16 | 136.81 (14) |
C13—C8—C7 | 113.68 (12) | C18—C17—C14 | 115.35 (13) |
C10—C9—C8 | 119.23 (14) | C16—C17—C14 | 107.80 (13) |
C10—C9—H9 | 120.4 | C17—C18—C7 | 112.45 (12) |
C8—C9—H9 | 120.4 | C17—C18—H18 | 123.8 |
C11—C10—C9 | 120.73 (15) | C7—C18—H18 | 123.8 |
C6—C1—C2—C3 | 0.9 (2) | C4—C5—C14—C17 | −125.40 (15) |
C1—C2—C3—C4 | −2.3 (2) | C6—C5—C14—C17 | 56.01 (15) |
C2—C3—C4—C5 | 0.8 (2) | C4—C5—C14—C13 | 121.57 (15) |
C3—C4—C5—C6 | 2.0 (2) | C6—C5—C14—C13 | −57.03 (14) |
C3—C4—C5—C14 | −176.46 (13) | C12—C13—C14—C15 | 13.99 (19) |
C2—C1—C6—C5 | 1.9 (2) | C8—C13—C14—C15 | −167.52 (11) |
C2—C1—C6—C7 | 179.78 (14) | C12—C13—C14—C17 | 129.29 (14) |
C4—C5—C6—C1 | −3.4 (2) | C8—C13—C14—C17 | −52.22 (14) |
C14—C5—C6—C1 | 175.29 (12) | C12—C13—C14—C5 | −117.89 (14) |
C4—C5—C6—C7 | 178.45 (12) | C8—C13—C14—C5 | 60.60 (13) |
C14—C5—C6—C7 | −2.83 (17) | C16—O2—C15—O1 | −179.23 (15) |
C1—C6—C7—C8 | −118.49 (16) | C16—O2—C15—C14 | 1.30 (19) |
C5—C6—C7—C8 | 59.48 (15) | C17—C14—C15—O1 | 178.30 (16) |
C1—C6—C7—C18 | 128.95 (16) | C5—C14—C15—O1 | 61.1 (2) |
C5—C6—C7—C18 | −53.07 (16) | C13—C14—C15—O1 | −64.7 (2) |
C18—C7—C8—C9 | −125.80 (15) | C17—C14—C15—O2 | −2.28 (16) |
C6—C7—C8—C9 | 121.28 (15) | C5—C14—C15—O2 | −119.45 (14) |
C18—C7—C8—C13 | 57.06 (14) | C13—C14—C15—O2 | 114.75 (14) |
C6—C7—C8—C13 | −55.86 (15) | C15—O2—C16—C17 | 0.30 (19) |
C13—C8—C9—C10 | 1.4 (2) | O2—C16—C17—C18 | −178.90 (18) |
C7—C8—C9—C10 | −175.55 (13) | O2—C16—C17—C14 | −1.73 (17) |
C8—C9—C10—C11 | 0.0 (2) | C15—C14—C17—C18 | −179.75 (13) |
C9—C10—C11—C12 | −1.2 (2) | C5—C14—C17—C18 | −55.14 (16) |
C10—C11—C12—C13 | 0.9 (2) | C13—C14—C17—C18 | 56.61 (16) |
C11—C12—C13—C8 | 0.5 (2) | C15—C14—C17—C16 | 2.39 (16) |
C11—C12—C13—C14 | 178.84 (12) | C5—C14—C17—C16 | 127.00 (13) |
C9—C8—C13—C12 | −1.7 (2) | C13—C14—C17—C16 | −121.24 (13) |
C7—C8—C13—C12 | 175.68 (11) | C16—C17—C18—C7 | 175.33 (18) |
C9—C8—C13—C14 | 179.70 (11) | C14—C17—C18—C7 | −1.69 (19) |
C7—C8—C13—C14 | −2.94 (15) | C8—C7—C18—C17 | −54.71 (16) |
C4—C5—C14—C15 | −9.8 (2) | C6—C7—C18—C17 | 56.09 (17) |
C6—C5—C14—C15 | 171.65 (12) |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg1i | 0.98 | 2.92 | 3.7835 (16) | 148 |
C16—H16B···Cg1ii | 0.97 | 2.76 | 3.650 (2) | 153 |
C18—H18···Cg2i | 0.93 | 2.84 | 3.3942 (16) | 120 |
C3—H3···O1iii | 0.93 | 2.64 | 3.519 (2) | 157 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z. |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cg1i | 0.98 | 2.92 | 3.7835 (16) | 148 |
C16—H16B···Cg1ii | 0.97 | 2.76 | 3.650 (2) | 153 |
C18—H18···Cg2i | 0.93 | 2.84 | 3.3942 (16) | 120 |
C3—H3···O1iii | 0.93 | 2.64 | 3.519 (2) | 157 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z. |
Acknowledgements
EMM is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of Senior Research Fellowship. The authors are grateful to Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India for single-crystal X-ray diffraction measurements.
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Dibenzobarrelene derivatives have been used as the key intermediates in the synthesis of several compounds which show various biological activities. Besides, they have showed application in drug development for various diseases (Khalil et al., 2010) and in the alignment of nematic liquid crystals (Cox et al., 2013). As a continuous work on the dibenzobarrelene compounds, a new dibenzobarrelene derivative, 3,5-dihydro-5,9 b-o-benzonaphtho [1,2-c] furan-1-one, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.
The compound crystallizes in monoclinic space group P21/c. The dihedral angle of the two aromatic rings of the anthracene moiety is 66.79 (7)°. The five-membered heterocyclic ring C14–17/O2 is almost planar with a maximum deviation of 0.014 (1)° for C14 carbon atom in the ring. One of the fused six-membered ring of the molecule C5—C8/C13/C14 is in boat conformation [φ = 117.52 (10)° and θ = 90.62 (10)°] having total puckering amplitude QT of 0.8495 (15) Å. The other six-membered ring C5—C7/C14/C17/C18 is also in boat conformation [φ = 302.45 (11)° and θ = 89.63 (12)°] having total puckering amplitude QT of 0.7919 (15) Å. Another six-membered ring C7/C8/C13/C14/C17/C18 is also in the same conformation [φ = 181.09 (11)° and θ = 90.35 (11)°] having total puckering amplitude QT of 0.7915 (15) Å (Cremer & Pople, 1975).
Three C–H···π interactions (Fig. 2) are found in the molecule. Whilst the two C–H···π interactions exist between the H atoms attached at the C7 and C16 atoms and the aromatic rings (C1—C6) of the anthracene moiety of two adjacent molecules from opposite sides of the main molecule, the third C–H···π interaction exists between the hydrogen at C18 atom and the C8—C13 ring of one of the above neighbouring molecules respectively with H···π distances of 2.92, 2.76 and 2.84 Å (Table 1). There are very weak π···π interactions between the aromatic rings of the anthracene moiety with centroid-centroid distances greater than 4 Å. However, packing of molecules is predominantly favored by the C–H···π interactions. Similar intermolecular interactive behaviour was found in the compound 8-phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18- heptane (Mathew et al., 2013). Fig. 3 shows the packing diagram of the title compound along a axis.