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Volume 68 
Part 4 
Page o1015  
April 2012  

Received 4 March 2012
Accepted 4 March 2012
Online 10 March 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.136
Data-to-parameter ratio = 15.6
Details
Open access

(2E)-2-[(2H-1,3-Benzodioxol-5-yl)methylidene]-2,3-dihydro-1H-inden-1-one

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia,bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C17H12O3, each of the five-membered rings in the inden-1-one and 1,3-benzodioxole residues is almost planar (r.m.s. deviations = 0.041 and 0.033 Å, respectively). A small twist about the single bond linking the two residues is evident [the C-C-C-C torsion angle = 8.7 (4)°]. Supramolecular zigzag layers propagating in the ac plane are formed in the crystal via C-H...O interactions. The layers are linked via [pi]-[pi] interactions between the five- and six-membered rings of 1,3-benzodioxole residues [centroid-centroid distance = 3.4977 (14) Å].

Related literature

For the biological activity of related species, see: Vera-DiVaio et al. (2009[Vera-DiVaio, M. A. F., Freitas, A. C. C., Castro, F. H. C., de Albuquerque, S., Cabral, L. M., Rodrigues, C. R., Albuquerque, M. G., Martins, R. C. A., Henriques, M. G. M. O. & Dias, L. R. S. (2009). Bioorg. Med. Chem. 17, 295-302.]). For related structures, see: Asiri et al. (2012a[Asiri, A. M., Faidallah, H. M., Al-Nemari, K. F., Ng, S. W. & Tiekink, E. R. T. (2012a). Acta Cryst. E68, o755.],b[Asiri, A. M., Faidallah, H. M., Al-Nemari, K. F., Ng, S. W. & Tiekink, E. R. T. (2012b). Acta Cryst. E68, o814.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12O3

  • Mr = 264.27

  • Orthorhombic, P b c a

  • a = 12.6102 (12) Å

  • b = 7.3497 (10) Å

  • c = 26.569 (4) Å

  • V = 2462.5 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.35 × 0.10 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.967, Tmax = 0.995

  • 6424 measured reflections

  • 2820 independent reflections

  • 1697 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.136

  • S = 0.98

  • 2820 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.95 2.47 3.290 (3) 144
C17-H17A...O1ii 0.99 2.46 3.302 (3) 143
Symmetry codes: (i) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6667 ).


Acknowledgements

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Asiri, A. M., Faidallah, H. M., Al-Nemari, K. F., Ng, S. W. & Tiekink, E. R. T. (2012a). Acta Cryst. E68, o755.  [CrossRef] [details]
Asiri, A. M., Faidallah, H. M., Al-Nemari, K. F., Ng, S. W. & Tiekink, E. R. T. (2012b). Acta Cryst. E68, o814.  [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vera-DiVaio, M. A. F., Freitas, A. C. C., Castro, F. H. C., de Albuquerque, S., Cabral, L. M., Rodrigues, C. R., Albuquerque, M. G., Martins, R. C. A., Henriques, M. G. M. O. & Dias, L. R. S. (2009). Bioorg. Med. Chem. 17, 295-302.  [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o1015  [ doi:10.1107/S1600536812009464 ]

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