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Crystal structure of (4-chloro-phen-yl)[2-(10-hy-droxy-phenanthren-9-yl)phenanthro[9,10-b]furan-3-yl]methanone.

Sajitha LU, Sithambaresan M, Jacob JP, Kurup MR - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: In the title compound, C37H21ClO3, the dihedral angle between the two phenanthrene moieties is 57.79 (5)°.The furan and one of the phenanthrene groups are fused in an almost coplanar arrangement [dihedral angle = 5.14 (8)°] and the furan unit makes dihedral angles of 70.27 (11) and 57.58 (8)° with the planes of the phenyl and the second phenanthrene group, respectively.A non-classical C-H⋯Cl inter-action [3.564 (2) Å] and three C-H⋯π inter-actions, with C⋯π distances of 3.709 (3), 3.745 (2) and 3.628 (3) Å, connect the mol-ecules, forming a three-dimensional supra-molecular architecture in the solid state.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India.

ABSTRACT
In the title compound, C37H21ClO3, the dihedral angle between the two phenanthrene moieties is 57.79 (5)°. The furan and one of the phenanthrene groups are fused in an almost coplanar arrangement [dihedral angle = 5.14 (8)°] and the furan unit makes dihedral angles of 70.27 (11) and 57.58 (8)° with the planes of the phenyl and the second phenanthrene group, respectively. In the crystal, neighbouring mol-ecules are connected via two inter-molecular hydrogen-bonding inter-actions (O-H⋯O and C-H⋯O) towards the carbonyl O atom with donor-acceptor distances of 2.824 (2) and 3.277 (3) Å, creating an inversion dimer. A non-classical C-H⋯Cl inter-action [3.564 (2) Å] and three C-H⋯π inter-actions, with C⋯π distances of 3.709 (3), 3.745 (2) and 3.628 (3) Å, connect the mol-ecules, forming a three-dimensional supra-molecular architecture in the solid state.

No MeSH data available.


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Reaction scheme showing the synthesis of the title compound (3).
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fig5: Reaction scheme showing the synthesis of the title compound (3).

Mentions: A mixture of phenanthrene­quinone (1) (5.2 g, 25 mmol), 4-chloro­aceto­phenone (2) (4.2 g, 27 mmol) and powdered potassium hydroxide (1 g) in methanol (30 ml) was stirred at 333 K for 4 h and then kept in a refrigerator for 48 h. The main product obtained was a 3(2H)-furan­one [2-(4-chloro­phen­yl)-2-hy­droxy-1-oxa­cyclo­penta­[l]phenanthren-3-one] (4) (65%), which was purified by recrystallization from a mixture of methanol and di­chloro­methane (2:1 v/v). The title compound (3) was the minor product formed along with (4) during the reaction (Fig. 5 ▶). The reaction mixture was filtered and the filtrate was concentrated and subjected to column chromatography over silica gel. The title compound (14%) was separated on elution with a mixture of hexane and ethyl acetate (2:3 v/v). Diffraction-quality single crystals were generated by slow evaporation from methanol. Yield 1.90 g (14%); m.p. 459 K; IR (KBr, νmax): 3374 (OH), 1591 (C=O) cm−1; 1H NMR (CDCl3): δ 8.79–7.26 (m, 20H), 8.69 (s, 1H); MS: m/z 548 (M+). Analysis calculated for C37H21ClO3: C 80.94, H 3.86%; found: C 80.82, H 3.66%.


Crystal structure of (4-chloro-phen-yl)[2-(10-hy-droxy-phenanthren-9-yl)phenanthro[9,10-b]furan-3-yl]methanone.

Sajitha LU, Sithambaresan M, Jacob JP, Kurup MR - Acta Crystallogr Sect E Struct Rep Online (2014)

Reaction scheme showing the synthesis of the title compound (3).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257253&req=5

fig5: Reaction scheme showing the synthesis of the title compound (3).
Mentions: A mixture of phenanthrene­quinone (1) (5.2 g, 25 mmol), 4-chloro­aceto­phenone (2) (4.2 g, 27 mmol) and powdered potassium hydroxide (1 g) in methanol (30 ml) was stirred at 333 K for 4 h and then kept in a refrigerator for 48 h. The main product obtained was a 3(2H)-furan­one [2-(4-chloro­phen­yl)-2-hy­droxy-1-oxa­cyclo­penta­[l]phenanthren-3-one] (4) (65%), which was purified by recrystallization from a mixture of methanol and di­chloro­methane (2:1 v/v). The title compound (3) was the minor product formed along with (4) during the reaction (Fig. 5 ▶). The reaction mixture was filtered and the filtrate was concentrated and subjected to column chromatography over silica gel. The title compound (14%) was separated on elution with a mixture of hexane and ethyl acetate (2:3 v/v). Diffraction-quality single crystals were generated by slow evaporation from methanol. Yield 1.90 g (14%); m.p. 459 K; IR (KBr, νmax): 3374 (OH), 1591 (C=O) cm−1; 1H NMR (CDCl3): δ 8.79–7.26 (m, 20H), 8.69 (s, 1H); MS: m/z 548 (M+). Analysis calculated for C37H21ClO3: C 80.94, H 3.86%; found: C 80.82, H 3.66%.

Bottom Line: In the title compound, C37H21ClO3, the dihedral angle between the two phenanthrene moieties is 57.79 (5)°.The furan and one of the phenanthrene groups are fused in an almost coplanar arrangement [dihedral angle = 5.14 (8)°] and the furan unit makes dihedral angles of 70.27 (11) and 57.58 (8)° with the planes of the phenyl and the second phenanthrene group, respectively.A non-classical C-H⋯Cl inter-action [3.564 (2) Å] and three C-H⋯π inter-actions, with C⋯π distances of 3.709 (3), 3.745 (2) and 3.628 (3) Å, connect the mol-ecules, forming a three-dimensional supra-molecular architecture in the solid state.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India.

ABSTRACT
In the title compound, C37H21ClO3, the dihedral angle between the two phenanthrene moieties is 57.79 (5)°. The furan and one of the phenanthrene groups are fused in an almost coplanar arrangement [dihedral angle = 5.14 (8)°] and the furan unit makes dihedral angles of 70.27 (11) and 57.58 (8)° with the planes of the phenyl and the second phenanthrene group, respectively. In the crystal, neighbouring mol-ecules are connected via two inter-molecular hydrogen-bonding inter-actions (O-H⋯O and C-H⋯O) towards the carbonyl O atom with donor-acceptor distances of 2.824 (2) and 3.277 (3) Å, creating an inversion dimer. A non-classical C-H⋯Cl inter-action [3.564 (2) Å] and three C-H⋯π inter-actions, with C⋯π distances of 3.709 (3), 3.745 (2) and 3.628 (3) Å, connect the mol-ecules, forming a three-dimensional supra-molecular architecture in the solid state.

No MeSH data available.


Related in: MedlinePlus