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

Gao, L.-J.; Liu, Y.

doi:10.1107/S1600536812045229

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 (C-C) = 0.004 Å
R = 0.040
wR = 0.119
Data-to-parameter ratio = 12.7
Details

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

Li-Jiu Gao ^a and Yun Liu ^a ^*

^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-HO interactions.

Related literature

For the properties of substituted naphthoquinones, see: Batton et al. (2000); Monks et al. (1992). For standard bond lengths, see: Allen et al. (1987). For the structure of 2-hydroxyquinoxaline, see: Stepien et al. (1976).

Experimental

Crystal data

C₁₇H₁₂ClNO₂
M_r = 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 radiation
= 0.28 mm^-1
T = 296 K
0.2 × 0.2 × 0.1 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (XCAD4; Harms & Wocadlo, 1995) T_min = 0.946, T_max = 0.972
15471 measured reflections
2479 independent reflections
2420 reflections with I > 2(I)
R_int = 0.036
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2(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
_max = 0.41 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N-HO2	0.70 (2)	2.23 (3)	2.611 (3)	116 (2)

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 and PLATON (Spek, 2009).

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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stepien, A., Grabowski, M. J., Cygler, M. & Wajsman, E. (1976). Acta Cryst. B32, 2048-2050.

organic compounds