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Volume 69 
Part 2 
Page o224  
February 2013  

Received 29 November 2012
Accepted 6 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.148
Data-to-parameter ratio = 16.6
Details
Open access

Dimethyl 2-[(acridin-9-yl)methylidene]malonate

aLaboratório de Imunopatologia Keizo Asami (LIKA), Departamento de Bioquímica, Universidade Federal de Pernambuco, 50670-901 Recife, PE, Brazil,bLaboratório de Síntese e Planejamento de Fármacos, Departamento de Antibióticos, Universidade Federal de Pernambuco, 50670-910 Recife, PE, Brazil,cLaboratório de Síntese e Vetorização de Moléculas Bioativas, Universidade Estadual da Paraíba, 58020-540 João Pessoa, PB, Brazil, and dDepartamento de Física e Informática, Instituto de Física de São Carlos, Universidade de São Paulo - USP, 13560-970 São Carlos, SP, Brazil
Correspondence e-mail: casimone@ifsc.usp.br

In the title compound, C19H15NO4, the acridine system is essentially planar (r.m.s. deviation = 0.015 Å). The crystal packing exhibits [pi]-[pi] interactions between pairs of centrosymmetric molecules, one of them between the central heterocyclic rings and others between the outer benzene rings of the acridine systems, with centroid-centroid distances of 3.692 (1) and 3.754 (1) Å, respectively. These pairs are further linked by additional [pi]-[pi] interactions along the a-axis direction through one of the two outer benzene ring of neighboring molecules, with a centroid-centroid distance of 3.642 (2) Å.

Related literature

For background to acridines, see: Kumar et al. (2012[Kumar, R., Kaur, M. & Kumari, M. (2012). Acta Pol. Pharm. 69, 3-9.]). For the biological activity of acridine derivatives, see: Pigatto et al. (2011[Pigatto, M. C., Lima, M. C. A., Galdino, S. L., Pitta, I. R., Vessecchi, R., Assis, M. D., Santos, J. S., Costa, T. C. T. D. & Lopes, P. N. (2011). Eur. J. Med. Chem. 1, 4245-4251.]); Das et al. (2011[Das, S., Kundu, S. & Suresh, K. G. (2011). DNA Cell Biol. 30, 525-535.]); Kumar et al. (2012[Kumar, R., Kaur, M. & Kumari, M. (2012). Acta Pol. Pharm. 69, 3-9.]). For the synthesis of acridines, see: Tomar et al. (2010[Tomar, V., Bhattacharjee, G., Uddin, K., Rajakumar, S., Srivastava, K. & Puri, S. K. (2010). Eur. J. Med. Chem. 45, 745-751.]). For related structures, see: Buckleton & Waters (1984[Buckleton, J. S. & Waters, T. N. (1984). Acta Cryst. C40, 1587-1589.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15NO4

  • Mr = 321.32

  • Triclinic, [P \overline 1]

  • a = 8.3022 (2) Å

  • b = 9.0208 (3) Å

  • c = 12.0334 (4) Å

  • [alpha] = 96.468 (2)°

  • [beta] = 93.652 (2)°

  • [gamma] = 117.422 (2)°

  • V = 787.98 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.32 × 0.28 × 0.22 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 10674 measured reflections

  • 3626 independent reflections

  • 2805 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.148

  • S = 1.05

  • 3626 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: COLLECT (Nonius, 1997[Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2094 ).


Acknowledgements

This work received partial support from CNPq and PROPESQ/UEPB. The authors thank the Instituto de Física de São Carlos - USP for allowing the use of the KappaCCD diffractometer.

References

Buckleton, J. S. & Waters, T. N. (1984). Acta Cryst. C40, 1587-1589.  [CrossRef] [details]
Das, S., Kundu, S. & Suresh, K. G. (2011). DNA Cell Biol. 30, 525-535.  [ISI] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kumar, R., Kaur, M. & Kumari, M. (2012). Acta Pol. Pharm. 69, 3-9.  [ChemPort] [PubMed]
Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pigatto, M. C., Lima, M. C. A., Galdino, S. L., Pitta, I. R., Vessecchi, R., Assis, M. D., Santos, J. S., Costa, T. C. T. D. & Lopes, P. N. (2011). Eur. J. Med. Chem. 1, 4245-4251.  [ISI] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tomar, V., Bhattacharjee, G., Uddin, K., Rajakumar, S., Srivastava, K. & Puri, S. K. (2010). Eur. J. Med. Chem. 45, 745-751.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o224  [ doi:10.1107/S1600536813000500 ]

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