[2-(2-Meth­oxy-1-naphtho­yl)phen­yl](1-naphth­yl)methanone

G Jagadeesan; K Sethusankar; R Sivasakthikumaran; Arasambattu K Mohanakrishnan

doi:10.1107/S1600536811042747

. 2011 Oct 29;67(Pt 11):o3036. doi: 10.1107/S1600536811042747

[2-(2-Methoxy-1-naphthoyl)phenyl](1-naphthyl)methanone

G Jagadeesan ^a, K Sethusankar ^b,^*, R Sivasakthikumaran ^c, Arasambattu K Mohanakrishnan ^c

PMCID: PMC3247430 PMID: 22220048

Abstract

The title compound, C₂₉H₂₀O₃, adopts an ‘S’ conformation with a dihedral angle of 68.5 (2)° beween the two acetone planes. The central phenyl ring forms dihedral angles of 83.8 (4) and 84.5 (4)° with the naphthalene and methoxy-substituted naphthalene mean planes, respectively. Both carbonyl-group O atoms deviate significantly from the naphthalene moiety and the methoxy-substituted naphthalene moiety [0.574 (1) and −1.053 (1) Å, respectively]. The crystal packing is stabilized by C—H⋯O intermolecular interactions, generating C(7) chain and R ² ₂(10) graph-set motifs.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶). For related structures, see: Tsumuki et al. (2011 ▶); Jagadeesan et al. (2011 ▶); Judas et al. (1995 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₉H₂₀O₃
M _r = 416.45
Monoclinic,
a = 8.3950 (3) Å
b = 8.9983 (4) Å
c = 28.5375 (11) Å
β = 97.188 (2)°
V = 2138.80 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
26364 measured reflections
6299 independent reflections
3875 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.137
S = 1.00
6270 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042747/bt5676sup1.cif

e-67-o3036-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042747/bt5676Isup2.hkl

e-67-o3036-Isup2.hkl^{(300.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042747/bt5676Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.49	3.392 (2)	164
C13—H13⋯O1ⁱⁱ	0.93	2.52	3.440 (2)	170
C27—H27⋯O2ⁱⁱⁱ	0.93	2.51	3.262 (3)	138

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

GJ and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, HOD, Department of Physics, for providing facilities in the department to carry out this work.

supplementary crystallographic information

Comment

Diketones are popular in organic synthesis, for their applications in biology and medicine. They are known to exhibit antioxidant, antitumour and antibacterial activities (Bennett et al., 1999).

X-ray analysis confirms the molecular structure and atom connectivity of the title compound as illustrated in the Fig. 1. The central phenyl ring (C12–C17) of the compound forms dihedral angles of 83.8 (4)° and 84.5 (4)° with the naphthalene moiety (C1–C10) and methoxy substituted naphthalene moiety (C19–28), respectively. The central phenyl ring (C12–C17) forms dihedral angles of 69.7 (5)° and 11.1 (5)° with the mean planes of the ketone groups, (C10–C12/O1) and (C17–C19/O2), respectively. The dihedral angle between the methoxy substituted naphthalene moiety (C19–C28) and naphthlene moiety (C1–C10) is 64.2 (4)°.

The two benzene rings (C1—C4/C9/C10) and (C4–C9) are almost coplanar with a dihedral angle of 2.26 (6)° between them. The atoms C29, O2 and O3 are having deviations of 0.363 (3) Å, -1.053 (1)Å and 0.101 (1)Å from the mean plane of the methoxy substituted naphthalene ring (C19–C28), respectively. The atom O1 deviates by 0.574 (1)Å from the plane of the naphthlene ring (C1–C10). The C10–C11 and C18–C19 bond lengths of 1.49 (2)Å and 1.50 (2)Å respectively and can be considered as single C(sp²)–C(sp²) bond distances. The molecule possesses distorted S–conformation in which C19/C18/C17/C12/C11/C10/O1/O2 are in a single plane, which is determined by the dihedral angle of 68.5 (2)° beween the planes defined by C19/C18/C17/O2 and that through C10/C11/C12/O1 (Judas et al., 1995).The title compound exhibits the structural similarities with the reported related structures (Tsumuki et al., 2011 & Jagadeesan et al., 2011).

The crystal packing is stabilized by C–H···O interactions (Table 1). The C3–H3···O1ⁱ interaction generates a C(7) chain along the a axis and the C13–H13···O1ⁱⁱ hydrogen bond generates R²₂(10) graphset motifs (Bernstein et al., 1995); the carbonyl-group O1 atom is involved in bifurcated hydrogen bonding. The Symmetry codes are: (i) x - 1, y, z; (ii) -x + 1, -y + 1, -z; (iii) -x + 1/2, y + 1/2, -z + 1/2. The packing view of the compound is shown in (Fig. 2).

Experimental

To a stirred suspension of 1-(2-methoxy-1-naphthoyl)phenyl-1-naphthyl- 2-benzofuran (1 g, 3.22 mmol) in dry THF (20 ml), lead tetraaccetate (1.52 g, 3.42 mmol) was added and refluxed at 343 K for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2x20 ml), washed with brine solution and dried (Na₂SO₄). The removal of solvent in vacuo afforded crude product. The crude product upon crystallization from methanol furnished the tittle compound as a colorless solid.