[3-Benzoyl-2,4-bis­(3-nitro­phen­yl)cyclo­but­yl](phen­yl)methanone

Nayak, P.S.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812044650

Volume 68
Part 12
Pages o3272-o3273
December 2012

Received 15 October 2012
Accepted 29 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.111
Data-to-parameter ratio = 17.1
Details

[3-Benzoyl-2,4-bis(3-nitrophenyl)cyclobutyl](phenyl)methanone

Prakash S. Nayak,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India,^bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The asymmetric unit of the title compound, C₃₀H₂₂N₂O₆, comprises a half-molecule of the cyclobutane derivative. The least-squares planes defined by the respective C atoms of the aromatic substituents intersect at angles of 76.81 (7) and 89.22 (8)° with the least-squares plane defined by the C atoms of the cyclobutane ring. In the crystal, C-HO contacts connect the molecules into a three-dimensional network. The shortest centroid-centroid distance between the two different aromatic rings is 3.9601 (8) Å.

Related literature

For the biological activity of chalcones and cyclobutane-derived compounds, see: Dimmock et al. (1999); Marais et al. (2005); Katerere et al. (2004); Seidel et al. (2000). For the crystal structures of similar compounds, see: Zheng et al. (2001); Zhuang & Zheng (2002). For general information about the dimerization of chalcones, see: Stobbe & Bremer (1929); Mustafa (1952). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₃₀H₂₂N₂O₆
M_r = 506.50
Monoclinic, P 2₁ /c
a = 5.7850 (1) Å
b = 14.7824 (3) Å
c = 14.3589 (3) Å
= 104.858 (1)°
V = 1186.86 (4) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 200 K
0.33 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.968, T_max = 0.989
11005 measured reflections
2945 independent reflections
2387 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.111
S = 1.03
2945 reflections
172 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O1ⁱ	1.00	2.56	3.3957 (15)	141
C14-H14O2ⁱⁱ	0.95	2.56	3.3666 (19)	142
C2-H2O3ⁱⁱⁱ	1.00	2.61	3.5009 (17)	148
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y, z-1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); 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) and Mercury (Macrae et al., 2008); 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: FJ2603 ).

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST-PURSE for financial assistance.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Katerere, D. R., Gray, A. I., Kennedy, A. R., Nash, R. J. & Waigh, R. D. (2004). Phytochemistry, 65, 433-438.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Marais, J. P. J., Ferreira, D. & Slade, D. (2005). Phytochemistry, 66, 2145-2176.
Mustafa, A. (1952). Chem. Rev. 51, 1-23.
Seidel, V., Bailleul, F. & Waterman, P. G. (2000). Phytochemistry, 55, 439-446.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stobbe, H. & Bremer, K. J. (1929). J. Prakt. Chem. 123, 1-60.
Zheng, Y., Zhuang, J.-P., Zhang, W.-Q., Leng, X.-B. & Weng, L.-H. (2001). Acta Cryst. E57, o1029-o1031.
Zhuang, J.-P. & Zheng, Y. (2002). Acta Cryst. E58, o1195-o1197.

organic compounds