Received 6 June 2013
In the title compound, C18H18ClNO4, the imide group with its two alkyl substituents is approximately perpendicular to the plane of the naphthoquinone ring system [dihedral angle = 78.5 (1)°]. Further, the imide carbonyl groups are oriented in an anti sense. In the crystal, the substituted naphthoquinone rings form - stacks in the a-axis direction [perpendicular centroid-centroid distance = 3.209 (2) Å and slippage = 4.401 Å].
For the synthesis and biological evaluation of some imido-substituted 1,4-naphthoquinone derivatives, see; Bakare et al. (2003); Berhe et al. (2008); Brandy et al. (2013). For the anti-cancer and anti-trypanosomal activity of the title compound, see; Bakare et al. (2003); Berhe et al. (2008); Khraiwesh et al. (2012).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5322 ).
This work was supported in part by grant No. 5-U54-CA914-31 (Howard University/Johns Hopkins Cancer Center Partnership); in part by grant G12MD007597 from the National Institute On Minority Health and Health Disparities of the National Institutes of Health; and in part by MRI grant No. CHE-1126533 from the NSF. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165-3170.
Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug. Des. Discov. 5, 485-488.
Brandy, Y., Brandy, N., Akinboye, E., Lewis, M., Mouamba, C., Mack, S., Butcher, R. J., Anderson, A. J. & Bakare, O. (2013). Molecules, 18, 1973-1984.
Khraiwesh, H. M., Lee, C. M., Brandy, Y., Akinboye, E. S., Berhe, S., Gittens, G., Abbas, M. M., Ampy, F. R., Ashraf, M. & Bakare, O. (2012). Arch. Pharm. Res. 35, 27-33.
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