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Volume 69 
Part 2 
Page o166  
February 2013  

Received 18 December 2012
Accepted 19 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.151
Data-to-parameter ratio = 12.8
Details
Open access

2,6-Dimethylphenyl acridine-9-carboxylate

aFaculty of Chemistry, University of Gdansk, J. Sobieskiego 18, 80-952 Gdansk, Poland
Correspondence e-mail: bla@chem.univ.gda.pl

In the title compound, C22H17NO2, the acridine ring system and the benzene ring are oriented at a dihedral angle of 37.7 (1)°. The carboxyl group is twisted at an angle of 67.7 (1)° relative to the acridine skeleton. In the crystal, molecules are arranged in stacks along the b axis, with all of the acridine rings involved in multiple [pi]-[pi] interactions [centroid-centroid distances in the range 3.632 (2)-4.101 (2) Å]. The acridine moieties are parallel within the stacks, but inclined at an angle of 52.7 (1)° in adjacent stacks.

Related literature

For general background, see: Krzyminski et al. (2011[Krzyminski, K., Ozóg, A., Malecha, P., Roshal, A. D., Wróblewska, A., Zadykowicz, B. & Blazejowski, J. (2011). J. Org. Chem. 76, 1072-1085.]); Natrajan et al. (2012[Natrajan, A., Sharpe, D. & Wen, D. (2012). Org. Biomol. Chem. 10, 3432-3447.]). For related structures, see: Sikorski et al. (2005[Sikorski, A., Krzyminski, K., Konitz, A. & Blazejowski, J. (2005). Acta Cryst. C61, o50-o52.]); Sikorski et al. (2006[Sikorski, A., Krzyminski, K., Bialonska, A., Lis, T. & Blazejowski, J. (2006). Acta Cryst. E62, o555-o558.]). For intermolecular interactions, see: Hunter et al. (2001[Hunter, C. A., Lawson, K. R., Perkins, J. & Urch, C. J. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 651-669.]). For the synthesis, see: Sato (1996[Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.]); Sikorski et al. (2005[Sikorski, A., Krzyminski, K., Konitz, A. & Blazejowski, J. (2005). Acta Cryst. C61, o50-o52.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17NO2

  • Mr = 327.37

  • Monoclinic, P 21 /c

  • a = 12.8617 (10) Å

  • b = 7.5352 (5) Å

  • c = 17.5950 (15) Å

  • [beta] = 103.143 (8)°

  • V = 1660.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.45 × 0.12 × 0.05 mm

Data collection
  • Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.349, Tmax = 1.000

  • 10387 measured reflections

  • 2913 independent reflections

  • 1908 reflections with I > 2[sigma](I)

  • Rint = 0.064

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.151

  • S = 0.97

  • 2913 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 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: NG5313 ).


Acknowledgements

This study was financed by the State Funds for Scientific Research through National Center for Science grant No. N N204 375 740 (contract No. 3757/B/H03/2011/40).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hunter, C. A., Lawson, K. R., Perkins, J. & Urch, C. J. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 651-669.
Krzyminski, K., Ozóg, A., Malecha, P., Roshal, A. D., Wróblewska, A., Zadykowicz, B. & Blazejowski, J. (2011). J. Org. Chem. 76, 1072-1085.  [PubMed]
Natrajan, A., Sharpe, D. & Wen, D. (2012). Org. Biomol. Chem. 10, 3432-3447.  [CrossRef] [ChemPort] [PubMed]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sikorski, A., Krzyminski, K., Bialonska, A., Lis, T. & Blazejowski, J. (2006). Acta Cryst. E62, o555-o558.  [CSD] [CrossRef] [details]
Sikorski, A., Krzyminski, K., Konitz, A. & Blazejowski, J. (2005). Acta Cryst. C61, o50-o52.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o166  [ doi:10.1107/S160053681205129X ]

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