[2-(3,4-Dimethyl­benzo­yl)phen­yl](4-meth­oxy­phen­yl)methanone

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

doi:10.1107/S1600536812047654

. 2012 Dec 5;69(Pt 1):o26. doi: 10.1107/S1600536812047654

[2-(3,4-Dimethylbenzoyl)phenyl](4-methoxyphenyl)methanone

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

PMCID: PMC3588237 PMID: 23476413

Abstract

The title molecule, C₂₃H₂₀O₃, is disordered with a 180° rotation about an axis normal to the length of the molecule, with the major and minor components in a 0.545 (5):0.455 (5) ratio. In the major component, the central benzene ring forms dihedral angles of 72.34 (3) and 69.46 (3)° with the dimethyl-substituted and methoxy-substituted benzene rings, respectively. Moreover, the central benzene ring forms dihedral angles of 50.86 (5) and 58.43 (4)° with the mean planes of the ketone groups. In the minor component, the corresponding dihedral angles between the benzene rings are 71.36 (4) and 67.94 (4)° and the dihedral angles between the benzene ring and the ketone groups are 56.44 (9) and 55.51 (8)°. In the crystal, C—H⋯O interactions generate a C(9) chain along the a-axis direction.

Related literature

For the uses and biological importance of diketones, see: Sugawara et al. (2001 ▶). For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978 ▶). For a related structure, see: Jagadeesan et al. (2011 ▶). graphic file with name e-69-00o26-scheme1.jpg

Experimental

Crystal data

C₂₃H₂₀O₃
M _r = 344.39
Monoclinic,
a = 21.983 (2) Å
b = 7.8173 (6) Å
c = 11.7489 (10) Å
β = 116.158 (2)°
V = 1812.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.972, T _max = 0.980
9619 measured reflections
4759 independent reflections
2728 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.173
S = 1.02
4759 reflections
388 parameters
353 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.16 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, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(30.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047654/pv2606sup1.cif

e-69-00o26-sup1.cif^{(30.5KB, cif)}

Click here for additional data file.^{(233.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047654/pv2606Isup2.hkl

e-69-00o26-Isup2.hkl^{(233.1KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812047654/pv2606Isup3.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
C23—H23B⋯O2ⁱ	0.96	2.32	3.23 (3)	159

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

The cyclic ketones play a significant role in increasing the red blood cells. They are also useful as hematopoietic agents in medicine, in particular, in the treatment of cancer, chemotherapy, radiotherapy and drug therapy (Sugawara et al., 2001). They are also important synthetic intermediates and starting materials in the synthesis of heterocyclic compounds (Hirsch & Bailey, 1978).

The molecular structure of the title compound is shown in Fig. 1. The molecule is disordered with 180° rotation about an axis normal to the length of the molecule. The unprimed atoms represent the major component where as the minor component is represented by primed ones. The site occupancy factors of the major and minor components refined to 0.545 (5) and 0.455 (5) values, respectively. The disorder prevents a discussion of accurate molecular geometry, though values are comparable to those reported in a closely related methanone derivative (Jagadeesan et al., 2011). The two overlapping molecules are shown in Fig. 2. There is a small separation between the coordinates of each pair of atoms. However, the atomic positions of all atoms in the two molecules are well resolved.

In the major component, the central benzene ring (C1–C6) forms dihedral angles of 72.34 (3) and 69.46 (3)° with the dimethyl substituted benzene ring (C8–C13) and methoxy substituted benzene ring (C17–22), respectively. Moreover, the benzene ring (C1–C6) forms dihedral angles of 50.86 (5) and 58.43 (4)° with the mean planes of the ketone groups (C1/C7/C8/O1) and (C6/C16/C17/O2), respectively. In the minor component, the central benzene ring (C1'–C6') forms dihedral angles of 71.36 (4) and 67.94 (4)° with the dimethyl substituted benzene ring (C8'–C13') and methoxy substituted benzene ring (C17'–C22'), respectively. Furthermore, the benzene ring (C1'–C6') forms dihedral angles of 56.44 (9) and 55.51 (8)° with the mean planes of the ketone groups (C1'/C7'/C8'/O1') and (C6'/C16'/C17'/O2'), respectively. The atoms C14 and O1 deviate significantly (-0.1305 (1) and -0.6096 (1) Å, respectively), from the mean plane of the benzene ring (C8–C13) and the atom O2 deviates by -0.6273 (2) Å from the mean plane of the methoxy substituted benzene ring (C17–22). On the other hand, the atom O1' deviates by -0.3678 (3) Å from the mean plane of the benzene ring (C8'–C13') and the atom O2' deviates by -0.3507 (2) Å from the mean plane of the methoxy substituted benzene ring (C17'–22').

The crystal packing is stabilized by C23–H23B···O2ⁱ intermolecular interactions (Tab. 1) generating a C(9) chain along the a axis (ⁱ: x + 1/2, y - 1/2, z + 1/2). The packing diagram of the crystal structure is shown in (Fig. 3).

Experimental

To a stirred suspension of [2-(3,4-dimethylbenzoyl)phenyl](4-methoxyphenyl) methanone (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.