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Volume 68 
Part 12 
Pages o3363-o3364  
December 2012  

Received 30 October 2012
Accepted 9 November 2012
Online 17 November 2012

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.135
Data-to-parameter ratio = 15.5
Details
Open access

Dibenzo[b,g]indeno[1',2':3,4]fluoreno[1,2-d]oxonine-5,11,16,21-tetraone

Shaaban Kamel Mohamed,a,b Mehmet Akkurt,c* Muhammad N. Tahir,d* Antar A. Abdelhamidb and Adel A. Marzouke

aChemistry Department, Faculty of Science, Minia University, Egypt,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
Correspondence e-mail: akkurt@erciyes.edu.tr, dmntahir_uos@yahoo.com

The asymmetric unit of the title compound, C34H16O5, contains two independent molecules (A and B) with similar conformations. The two benzene rings attached to the nine-membered ring are inclined to one another at 63.62 (14)° in molecule A and 68.23 (12)° in molecule B. One intramoleculer C-H...O hydrogen bond occurs in molecule A and two are observed in molecule B. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming a three-dimensional network structure with R22(10) and R22(24) ring motifs. Aromatic [pi]-[pi] stacking interactions [centroid-centroid distances = 3.7572 (19), 3.6996 (19) and 3.7043 (19) Å] are also observed. The unit cell contains a pair of voids of 37 (2) Å3 about an inversion centre but the residual electron density (highest peak = 0.19 e Å-3 and deepest hole = -0.20 e Å-3) in the difference Fourier map suggests that no solvent molecule occupies this void.

Related literature

1,3-Indandione undergoes self-condensation quite easily, see: Zargar & Khan (2012[Zargar, N. D. & Khan, K. Z. (2012). Global J. Sci. Frontier Res. B, XII, 45-48.]). For industrial and biological applications of indandion containing compounds see: Seniutinas et al. (2012[Seniutinas, G., Tomasiunas, R., Czapilicki, R., Sahraoui, B., Daskeviciene, M., Getaut, V. & Balveicius, Z. (2012). Dyes Pigm. 95, 33-40.]); Jin et al. (2009[Jin, M.-C., Cai, M.-Q. & Chen, X.-H. (2009). J. Anal. Toxicol. 33, 294-300.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C34H16O5

  • Mr = 504.47

  • Triclinic, [P \overline 1]

  • a = 12.230 (4) Å

  • b = 12.346 (3) Å

  • c = 16.794 (5) Å

  • [alpha] = 82.229 (7)°

  • [beta] = 72.773 (6)°

  • [gamma] = 81.181 (10)°

  • V = 2382.5 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.28 × 0.18 × 0.14 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.987

  • 38137 measured reflections

  • 10895 independent reflections

  • 4858 reflections with I > 2[sigma](I)

  • Rint = 0.061
Refinement

  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.135

  • S = 0.94

  • 10895 reflections

  • 704 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C24-H24...O10i 0.93 2.56 3.302 (3) 137
C30-H30...O5ii 0.93 2.60 3.507 (3) 166
C32-H32...O7iii 0.93 2.49 3.398 (3) 166
C33-H33...O4 0.93 2.32 3.087 (3) 139
C39-H39...O1iv 0.93 2.36 3.115 (3) 139
C56-H56...O8 0.93 2.52 3.210 (3) 131
C58-H58...O7v 0.93 2.52 3.377 (3) 154
C67-H67...O9 0.93 2.36 3.117 (3) 139
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x, -y+1, -z+2; (iii) x-1, y, z; (iv) x+1, y-1, z; (v) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: XU5643 ).

Acknowledgements

The authors are grateful to the Higher Education Ministry of Egypt, Manchester Metropolitan University, Erciyes University and the University of Sargodha for supporting this study.

References

Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.  [ISI] [CrossRef] [ChemPort] [details]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). 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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jin, M.-C., Cai, M.-Q. & Chen, X.-H. (2009). J. Anal. Toxicol. 33, 294-300.  [PubMed] [ChemPort]
Seniutinas, G., Tomasiunas, R., Czapilicki, R., Sahraoui, B., Daskeviciene, M., Getaut, V. & Balveicius, Z. (2012). Dyes Pigm. 95, 33-40.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zargar, N. D. & Khan, K. Z. (2012). Global J. Sci. Frontier Res. B, XII, 45-48.

Acta Cryst (2012). E68, o3363-o3364   [ doi:10.1107/S1600536812046363 ]

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