[Journal logo]

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 [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.111
Data-to-parameter ratio = 17.1
Details
Open access

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

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-H...O 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[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]); Marais et al. (2005[Marais, J. P. J., Ferreira, D. & Slade, D. (2005). Phytochemistry, 66, 2145-2176.]); Katerere et al. (2004[Katerere, D. R., Gray, A. I., Kennedy, A. R., Nash, R. J. & Waigh, R. D. (2004). Phytochemistry, 65, 433-438.]); Seidel et al. (2000[Seidel, V., Bailleul, F. & Waterman, P. G. (2000). Phytochemistry, 55, 439-446.]). For the crystal structures of similar compounds, see: Zheng et al. (2001[Zheng, Y., Zhuang, J.-P., Zhang, W.-Q., Leng, X.-B. & Weng, L.-H. (2001). Acta Cryst. E57, o1029-o1031.]); Zhuang & Zheng (2002[Zhuang, J.-P. & Zheng, Y. (2002). Acta Cryst. E58, o1195-o1197.]). For general information about the dimerization of chalcones, see: Stobbe & Bremer (1929[Stobbe, H. & Bremer, K. J. (1929). J. Prakt. Chem. 123, 1-60.]); Mustafa (1952[Mustafa, A. (1952). Chem. Rev. 51, 1-23.]). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C30H22N2O6

  • Mr = 506.50

  • Monoclinic, P 21 /c

  • a = 5.7850 (1) Å

  • b = 14.7824 (3) Å

  • c = 14.3589 (3) Å

  • [beta] = 104.858 (1)°

  • V = 1186.86 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.989

  • 11005 measured reflections

  • 2945 independent reflections

  • 2387 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.111

  • S = 1.03

  • 2945 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1i 1.00 2.56 3.3957 (15) 141
C14-H14...O2ii 0.95 2.56 3.3666 (19) 142
C2-H2...O3iii 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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [ChemPort] [ISI]
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.  [ISI] [PubMed] [ChemPort]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Katerere, D. R., Gray, A. I., Kennedy, A. R., Nash, R. J. & Waigh, R. D. (2004). Phytochemistry, 65, 433-438.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Marais, J. P. J., Ferreira, D. & Slade, D. (2005). Phytochemistry, 66, 2145-2176.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mustafa, A. (1952). Chem. Rev. 51, 1-23.  [CrossRef] [ChemPort] [ISI]
Seidel, V., Bailleul, F. & Waterman, P. G. (2000). Phytochemistry, 55, 439-446.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stobbe, H. & Bremer, K. J. (1929). J. Prakt. Chem. 123, 1-60.  [CrossRef] [ChemPort]
Zheng, Y., Zhuang, J.-P., Zhang, W.-Q., Leng, X.-B. & Weng, L.-H. (2001). Acta Cryst. E57, o1029-o1031.  [CSD] [CrossRef] [details]
Zhuang, J.-P. & Zheng, Y. (2002). Acta Cryst. E58, o1195-o1197.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3272-o3273   [ doi:10.1107/S1600536812044650 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.