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Volume 68 
Part 12 
Page o3378  
December 2012  

Received 14 August 2012
Accepted 1 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.040
wR = 0.119
Data-to-parameter ratio = 12.7
Details
Open access

2-Chloro-3-(4-methylanilino)naphthalene-1,4-dione

aDepartment of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, People's Republic of China
Correspondence e-mail: liu_yun3@sina.com.cn

In the title compound, C17H12ClNO2, the naphthoquinone system is essentially planar [maximum deviation = 0.078 (2) Å] and makes a dihedral angle of 52.38 (7)° with the benzene ring. The crystal structure features N-H...O interactions.

Related literature

For the properties of substituted naphthoquinones, see: Batton et al. (2000[Batton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G. & Monks, T. J. (2000). Chem. Res. Toxicol. 13, 135-160.]); Monks et al. (1992[Monks, T. J., Hanzlik, R. P., Cohen, G. M., Ross, D. & Graham, D. G. (1992). Toxicol. Appl. Pharmacol. 112, 2-16.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the structure of 2-hydroxyquinoxaline, see: Stepien et al. (1976[Stepien, A., Grabowski, M. J., Cygler, M. & Wajsman, E. (1976). Acta Cryst. B32, 2048-2050.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12ClNO2

  • Mr = 297.73

  • Orthorhombic, P n a 21

  • a = 12.1614 (10) Å

  • b = 22.4915 (18) Å

  • c = 5.0444 (4) Å

  • V = 1379.79 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 296 K

  • 0.2 × 0.2 × 0.1 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (XCAD4; Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]) Tmin = 0.946, Tmax = 0.972

  • 15471 measured reflections

  • 2479 independent reflections

  • 2420 reflections with I > 2[sigma](I)

  • Rint = 0.036

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.119

  • S = 1.27

  • 2479 reflections

  • 195 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N-H...O2 0.70 (2) 2.23 (3) 2.611 (3) 116 (2)

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius. (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2213 ).


Acknowledgements

The authors acknowledge the financial support of Xuzhou City (XZZD1213).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Batton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G. & Monks, T. J. (2000). Chem. Res. Toxicol. 13, 135-160.  [PubMed]
Enraf-Nonius. (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Monks, T. J., Hanzlik, R. P., Cohen, G. M., Ross, D. & Graham, D. G. (1992). Toxicol. Appl. Pharmacol. 112, 2-16.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stepien, A., Grabowski, M. J., Cygler, M. & Wajsman, E. (1976). Acta Cryst. B32, 2048-2050.  [CrossRef] [details] [ISI]


Acta Cryst (2012). E68, o3378  [ doi:10.1107/S1600536812045229 ]

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