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Volume 69 
Part 8 
Page o1230  
August 2013  

Received 6 June 2013
Accepted 12 June 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.007 Å
R = 0.077
wR = 0.227
Data-to-parameter ratio = 15.5
Details
Open access

N-Butanoyl-N-(3-chloro-1,4-dioxonaphthalen-2-yl)butanamide

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and bDepartment of Natural Sciences, Bowie State University, Bowie, MD 20715, USA
Correspondence e-mail: rbutcher99@yahoo.com

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 [pi]-[pi] stacks in the a-axis direction [perpendicular centroid-centroid distance = 3.209 (2) Å and slippage = 4.401 Å].

Related literature

For the synthesis and biological evaluation of some imido-substituted 1,4-naphthoquinone derivatives, see; Bakare et al. (2003[Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165-3170.]); Berhe et al. (2008[Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug. Des. Discov. 5, 485-488.]); Brandy et al. (2013[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.]). For the anti-cancer and anti-trypanosomal activity of the title compound, see; Bakare et al. (2003[Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165-3170.]); Berhe et al. (2008[Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug. Des. Discov. 5, 485-488.]); Khraiwesh et al. (2012[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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18ClNO4

  • Mr = 347.78

  • Triclinic, [P \overline 1]

  • a = 8.1717 (10) Å

  • b = 8.3117 (10) Å

  • c = 14.6841 (15) Å

  • [alpha] = 93.119 (9)°

  • [beta] = 98.369 (10)°

  • [gamma] = 118.043 (12)°

  • V = 862.23 (17) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.15 mm-1

  • T = 295 K

  • 0.36 × 0.28 × 0.08 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.530, Tmax = 1.000

  • 5454 measured reflections

  • 3398 independent reflections

  • 2122 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.227

  • S = 1.12

  • 3398 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5322 ).


Acknowledgements

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.

References

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.  [CrossRef] [PubMed] [ChemPort]
Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug. Des. Discov. 5, 485-488.  [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort] [PubMed]
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.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1230  [ doi:10.1107/S1600536813016401 ]

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