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Volume 69 
Part 2 
Page o305  
February 2013  

Received 18 January 2013
Accepted 21 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.073
wR = 0.203
Data-to-parameter ratio = 12.7
Details
Open access

Phenyl acridine-9-carboxylate

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

The acridine ring system and the benzene ring in the title compound, C20H13NO2, are oriented at a dihedral angle of 6.4 (2)°. The carboxyl group is twisted at an angle of 83.6 (2)° relative to the acridine skeleton. The molecules in the crystal are arranged in stacks along the b axis, with two of the acridine rings involved in multiple [pi]-[pi] interactions [centroid-centroid distances in the range 3.536 (2)-3.894 (2) Å]. Stacks arranged parallel are linked via C-H...[pi] interactions, forming layers in the ac plane that are in contact with adjacent, inversely oriented layers via other C-H...[pi] interactions, giving rise to double layers. The inversely oriented double layers interact dispersively. The acridine units are parallel within the parallel-oriented stacks, but inclined at an angle of 79.6 (2)° in the inversely oriented stacks.

Related literature

For general background to the applications of the title compound, 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.]); Trzybinski et al. (2010[Trzybinski, D., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o906-o907.]). For related structures, see: Trzybinski et al. (2013[Trzybinski, D., Wera, M., Krzyminski, K. & Blazejowski, J. (2013). Acta Cryst. E69, o166.]). 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.]); Takahashi et al. (2001[Takahashi, O., Kohno, Y., Iwasaki, S., Saito, K., Iwaoka, M., Tomada, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2001). Bull. Chem. Soc. Jpn, 74, 2421-2430.]). For the synthesis, see: Sato (1996[Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.]); Trzybinski et al. (2010[Trzybinski, D., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o906-o907.]).

[Scheme 1]

Experimental

Crystal data
  • C20H13NO2

  • Mr = 299.31

  • Monoclinic, P 21 /c

  • a = 17.094 (2) Å

  • b = 5.4175 (7) Å

  • c = 16.310 (2) Å

  • [beta] = 95.545 (11)°

  • V = 1503.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.6 × 0.2 × 0.1 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, England.]) Tmin = 0.354, Tmax = 0.986

  • 9221 measured reflections

  • 2651 independent reflections

  • 1560 reflections with I > 2[sigma](I)

  • Rint = 0.068

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.203

  • S = 1.04

  • 2651 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 denote the centroids of the C1-C4/C11/C12 and C18-C23 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3...Cg2i 0.93 2.98 3.712 (3) 137
C7-H7...Cg4ii 0.93 2.84 3.646 (3) 145
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: XU5671 ).


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. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [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, England.
Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Takahashi, O., Kohno, Y., Iwasaki, S., Saito, K., Iwaoka, M., Tomada, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2001). Bull. Chem. Soc. Jpn, 74, 2421-2430.  [ISI] [CrossRef] [ChemPort]
Trzybinski, D., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o906-o907.  [CrossRef] [details]
Trzybinski, D., Wera, M., Krzyminski, K. & Blazejowski, J. (2013). Acta Cryst. E69, o166.  [CrossRef] [details]


Acta Cryst (2013). E69, o305  [ doi:10.1107/S1600536813002055 ]

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