2,6-Dimethyl­phenyl acridine-9-carboxyl­ate

Trzybiński, D.; Wera, M.; Krzymiński, K.; Błażejowski, J.

doi:10.1107/S160053681205129X

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.151
Data-to-parameter ratio = 12.8
Details

2,6-Dimethylphenyl acridine-9-carboxylate

Damian Trzybinski,^a Michal Wera,^a Karol Krzyminski ^a and Jerzy Blazejowski ^a ^*

^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); Natrajan et al. (2012). For related structures, see: Sikorski et al. (2005); Sikorski et al. (2006). For intermolecular interactions, see: Hunter et al. (2001). For the synthesis, see: Sato (1996); Sikorski et al. (2005).

Experimental

Crystal data

C₂₂H₁₇NO₂
M_r = 327.37
Monoclinic, P 2₁ /c
a = 12.8617 (10) Å
b = 7.5352 (5) Å
c = 17.5950 (15) Å
= 103.143 (8)°
V = 1660.6 (2) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.349, T_max = 1.000
10387 measured reflections
2913 independent reflections
1908 reflections with I > 2(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.151
S = 0.97
2913 reflections
228 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
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.
Natrajan, A., Sharpe, D. & Wen, D. (2012). Org. Biomol. Chem. 10, 3432-3447.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sato, N. (1996). Tetrahedron Lett. 37, 8519-8522.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sikorski, A., Krzyminski, K., Bialonska, A., Lis, T. & Blazejowski, J. (2006). Acta Cryst. E62, o555-o558.
Sikorski, A., Krzyminski, K., Konitz, A. & Blazejowski, J. (2005). Acta Cryst. C61, o50-o52.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds