(2-Benzoyl­phen­yl)(3,4-dimethyl­phen­yl)methanone

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

doi:10.1107/S1600536811029965

. 2011 Jul 30;67(Pt 8):o2177. doi: 10.1107/S1600536811029965

(2-Benzoylphenyl)(3,4-dimethylphenyl)methanone

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

PMCID: PMC3213611 PMID: 22091188

Abstract

In the title compound, C₂₂H₁₈O₂, the central benzene ring forms dihedral angles of 76.0 (1) and 73.1 (1)° with the phenyl ring and dimethyl-substituted benzene ring, respectively. The carbonyl-group O atoms deviate significantly from the phenyl ring and the dimethyl-substituted benzene ring [−0.582 (12) and 0.546 (12) Å, respectively]. The crystal packing is stabilized by C—H⋯π interactions.

Related literature

For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978 ▶). For chelating reagents of metallic systems, see: Liang et al. (2003 ▶). For related bond-length and angle values, see: Judaš & Kaitner (2005) ▶. For related structures, see: Khan et al. (2009 ▶); Narayanan et al. (2011 ▶).

Experimental

Crystal data

C₂₂H₁₈O₂
M _r = 314.36
Monoclinic,
a = 17.8606 (14) Å
b = 7.7590 (6) Å
c = 11.9722 (11) Å
β = 93.942 (3)°
V = 1655.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
17270 measured reflections
3862 independent reflections
2827 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.129
S = 1.01
3862 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029965/rk2286sup1.cif

e-67-o2177-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029965/rk2286Isup2.hkl

e-67-o2177-Isup2.hkl^{(185.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029965/rk2286Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.93	2.86	3.747 (2)	159
C21—H21A⋯Cg3ⁱⁱ	0.96	2.91	3.8144 (17)	157
C22—H22C⋯Cg3ⁱⁱⁱ	0.96	2.78	3.6484 (17)	152

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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 important synthetic intermediates and starting materials in the synthesis of many heterocyclic compounds (Hirsch & Bailey, 1978) and also employed as effective chelating reagents for a large number of metallic systems (Liang et al., 2003).

X-ray analysis confirms the molecular structure and atom connectivity of the title compound as illustrated in the Fig. 1. The bond lengths and bond angles are normal and correspond to those observed in 2-benzyl-1,3-diphenylpropane-1,3-dione (Judaš & Kaitner, 2005). The central phenyl ring (C8–C13) of the compound forms dihedral angles of 76.0 (1)° and 73.1 (1)° with the other phenyl rings (C1–C6) and (C15–C20), respectively. The central phenyl ring (C8–C13) forms dihedral angles of 53.3 (6)° and 58.8 (6)° with the mean plane of the ketone groups (C13–C15/O1) and (C6–C8/O2), respectively.

In the dimethyl substituted phenyl ring (C15–C20) the deviation of atoms C21 and C22 are -0.014 (2) Å and -0.049 (2) Å, respectively. The atom O1 deviates by -0.582 (1) Å from the plane of the phenyl ring (C1–C6). Also the atom O2 deviate by 0.546 (1) Å from the plane of the phenyl ring (C15–C20). The title compound exhibits the structural similarities with the already reported related structures (Khan et al., 2009; Narayanan et al., 2011).

The molecular structure is stabilized by C—H···Cg interactions - look Table 1. The Cg1 is center of gravity of (C1–C6) ring and Cg3 is center of gravity of (C15–C20) ring. Symmetry codes: (i) -x, y - 1/2, -z + 5/2; (ii) -x + 1, y - 1/2, -z + 3/2; (iii) -x + 1, -y + 1, -z + 2.

Experimental

To a stirred suspension of 1-(3,4-dimethylphenyl)-3-phenyl-2-benzofuran (1 g, 3.22 mmol) in dry THF (20 ml), lead tetraacetate (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 (2 × 20 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 title compound as a colourless solid.