11,12-Dichloro­dibenzo[a,c]phenazine

Imeri, A.; Glagovich, N.M.; Crundwell, G.

doi:10.1107/S1600536812049690

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 (C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 23.1
Details

11,12-Dichlorodibenzo[a,c]phenazine

Arta Imeri,^a Neil M. Glagovich ^a and Guy Crundwell ^a ^*

^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). For the structures of similar compounds, see: Bellizzi et al. (2006); Day et al. (2002); Richards et al. (2009).

Experimental

Crystal data

C₂₀H₁₀Cl₂N₂
M_r = 349.20
Monoclinic, C 2/c
a = 3.8583 (3) Å
b = 26.2739 (13) Å
c = 15.1147 (10) Å
= 94.877 (6)°
V = 1526.67 (17) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.915, T_max = 1.000
5082 measured reflections
2520 independent reflections
1372 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.104
S = 0.83
2520 reflections
109 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds