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

Almeida, S.M.V. de; Pitta, I.R.; Lima, M. do C.A. de; Mendonça Junior, F.J.B.; Simone, C.A. de

doi:10.1107/S1600536813000500

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 (C-C) = 0.002 Å
R = 0.052
wR = 0.148
Data-to-parameter ratio = 16.6
Details

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

Sinara M. V. de Almeida,^a Ivan R. Pitta,^b Maria do Carmo A. de Lima,^b Francisco J. B. Mendonça Junior ^c and Carlos A. de Simone ^d ^*

^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). For the biological activity of acridine derivatives, see: Pigatto et al. (2011); Das et al. (2011); Kumar et al. (2012). For the synthesis of acridines, see: Tomar et al. (2010). For related structures, see: Buckleton & Waters (1984).

Experimental

Crystal data

C₁₉H₁₅NO₄
M_r = 321.32
Triclinic, $[P \overline 1]$
a = 8.3022 (2) Å
b = 9.0208 (3) Å
c = 12.0334 (4) Å
= 96.468 (2)°
= 93.652 (2)°
= 117.422 (2)°
V = 787.98 (4) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.148
S = 1.05
3626 reflections
218 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.24 e Å^-3

Data collection: COLLECT (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Das, S., Kundu, S. & Suresh, K. G. (2011). DNA Cell Biol. 30, 525-535.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kumar, R., Kaur, M. & Kumari, M. (2012). Acta Pol. Pharm. 69, 3-9.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tomar, V., Bhattacharjee, G., Uddin, K., Rajakumar, S., Srivastava, K. & Puri, S. K. (2010). Eur. J. Med. Chem. 45, 745-751.

organic compounds