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Volume 66 
Part 7 
Page o1853  
July 2010  

Received 22 June 2010
Accepted 24 June 2010
Online 30 June 2010

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Key indicators
Single-crystal X-ray study
T = 158 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 13.4
Details
Open access

6,7-Dihydro-3H-1,4-diazepino[1,2,3,4-lmn][1,10]phenanthroline-3,9(5H)-dione

Said Nadeem,a Itrat Anis,b Donald VanDerveerc and Muhammad Raza Shaha*

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan,bDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, and cChemistry Department, Clemson University, Clemson, SC 29634-0973, USA
Correspondence e-mail: raza_shahm@yahoo.com

In the title compound, C15H12N2O2, the seven-membered ring bearing the three methylene C atoms displays a puckered conformation, with the methylene C atoms deviating from the plane of the benzene ring by 0.05 (1), 0.98 (1) and 1.04 (1) Å. The phenanthroline unit is not planar; the dihedral angles between this benzene ring and the other pyridyl rings are 9.62 (4) and 9.31 (4)°. The crystal packing is stabilized by [pi]-[pi] interactions between two phenanthroline ring systems, forming a centrosymmetric dimer with a centroid-centroid distance of 3.656 (1) Å.

Related literature

For background to [pi]-[pi] interactions in supramolecular chemistry, see: Sisson et al. (2006[Sisson, A. L., Shah, M. R., Bhosale, S. & Matile, S. (2006). Chem. Soc. Rev. 35, 1269-1286]). For a related structure, see: Nadeem et al. (2009[Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12N2O2

  • Mr = 252.27

  • Monoclinic, P 21 /n

  • a = 9.1853 (18) Å

  • b = 13.931 (3) Å

  • c = 9.4956 (19) Å

  • [beta] = 111.14 (3)°

  • V = 1133.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 158 K

  • 0.50 × 0.46 × 0.38 mm
Data collection

  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.]) Tmin = 0.952, Tmax = 0.963

  • 8367 measured reflections

  • 2309 independent reflections

  • 2115 reflections with I > 2[sigma](I)

  • Rint = 0.016
Refinement

  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.111

  • S = 1.06

  • 2309 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Data collection: CrystalClear (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL 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: NG2793 ).

Acknowledgements

The authors thank the Pakistan Science Foundation for financial support.

References

Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.
Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.  [CSD] [CrossRef] [details]
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sisson, A. L., Shah, M. R., Bhosale, S. & Matile, S. (2006). Chem. Soc. Rev. 35, 1269-1286  [ISI] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o1853  [ doi:10.1107/S1600536810024761 ]

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