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

Jagadeesan, G.; Sethusankar, K.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.

doi:10.1107/S1600536812047654

Volume 69
Part 1
Page o26
January 2013

Received 5 November 2012
Accepted 20 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean () = 0.000 Å
Disorder in main residue
R = 0.051
wR = 0.173
Data-to-parameter ratio = 12.3
Details

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

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

^aDepartment of Physics, Meenakshi College of Engineering, West K.K. Nagar, Chennai 600 078, India,^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

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-HO 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).

Experimental

Crystal data

C₂₃H₂₀O₃
M_r = 344.39
Monoclinic, C c
a = 21.983 (2) Å
b = 7.8173 (6) Å
c = 11.7489 (10) Å
= 116.158 (2)°
V = 1812.2 (3) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.173
S = 1.02
4759 reflections
388 parameters
353 restraints
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C23-H23BO2ⁱ	0.96	2.32	3.23 (3)	159
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: PV2606 ).

Acknowledgements

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

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Hirsch, S. S. & Bailey, W. J. (1978). J. Org. Chem. 43, 4090-4094.
Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.

organic compounds