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Volume 69 
Part 1 
Page o48  
January 2013  

Received 1 November 2012
Accepted 4 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 23.1
Details
Open access

11,12-Dichlorodibenzo[a,c]phenazine

aDepartment of Chemistry, Central Connecticut State University, New Britain, CT 06053, USA
Correspondence e-mail: crundwellg@mail.ccsu.edu

The title compound, C20H10Cl2N2, has crystallographic twofold rotational symmetry [maximum deviation from the least-squares plane = 0.038 (1) Å]. In the crystal, weak [pi]-[pi] ring stacking interactions occur down the a-axis direction [minimum centroid-centroid separation = 3.7163 (8) Å].

Related literature

For the synthesis of the title compound, see: Bellizzi et al. (2006[Bellizzi, M., Crundwell, G., Zeller, M., Hunter, A. D. & McBurney, B. (2006). Acta Cryst. E62, o5249-o5251.]). For the structures of similar compounds, see: Bellizzi et al. (2006[Bellizzi, M., Crundwell, G., Zeller, M., Hunter, A. D. & McBurney, B. (2006). Acta Cryst. E62, o5249-o5251.]); Day et al. (2002[Day, M. W., Amashukeli, X. A. & Gray, H. B. (2002). Private communication (refcode MIVRUE). CCDC, Cambridge, England.]); Richards et al. (2009[Richards, G. J., Hill, J. P., Okamoto, K., Shundo, A., Akada, M., Elsegood, M. R. J., Mori, T. & Ariga, K. (2009). Langmuir Lett. 25, 8408-8413.]).

[Scheme 1]

Experimental

Crystal data
  • C20H10Cl2N2

  • Mr = 349.20

  • Monoclinic, C 2/c

  • a = 3.8583 (3) Å

  • b = 26.2739 (13) Å

  • c = 15.1147 (10) Å

  • [beta] = 94.877 (6)°

  • V = 1526.67 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 293 K

  • 0.32 × 0.14 × 0.09 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.915, Tmax = 1.000

  • 5082 measured reflections

  • 2520 independent reflections

  • 1372 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.104

  • S = 0.83

  • 2520 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2242 ).


Acknowledgements

This research was funded by a CCSU-AAUP research grant.

References

Bellizzi, M., Crundwell, G., Zeller, M., Hunter, A. D. & McBurney, B. (2006). Acta Cryst. E62, o5249-o5251.  [CSD] [CrossRef] [details]
Day, M. W., Amashukeli, X. A. & Gray, H. B. (2002). Private communication (refcode MIVRUE). CCDC, Cambridge, England.
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Richards, G. J., Hill, J. P., Okamoto, K., Shundo, A., Akada, M., Elsegood, M. R. J., Mori, T. & Ariga, K. (2009). Langmuir Lett. 25, 8408-8413.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o48  [ doi:10.1107/S1600536812049690 ]

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