1-Benzyl-4-chloro­indoline-2,3-dione

Wang, D.C.; Leng, B.R.; Wang, G.B.; Wei, P.; Ou-yang, P.K.

doi:10.1107/S1600536811051816

Volume 68
Part 1
Page o37
January 2012

Received 27 November 2011
Accepted 1 December 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.064
wR = 0.117
Data-to-parameter ratio = 13.5
Details

1-Benzyl-4-chloroindoline-2,3-dione

De Cai Wang,^a ^* Bo Rong Leng,^a Gui Bin Wang,^b Ping Wei ^a and Ping Kai Ou-yang ^a

^aSate Key Laboratory of Materials-Oriented Chemcial Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bPRC DAYAOWAN Administration for Entry & Exit Inspection and Quarantine, Haiqingdao Foreign Area Development Zone, Dalian 116610, Liaoning Province, People's Republic of China
Correspondence e-mail: dc_wang@hotmail.com

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₀ClNO₂, which differ in the dihedral angles between the mean planes of the phenyl ring and the 4-chloroindoline-2,3-dione ring system [59.48 (9) and 79.0 (1)°]. In the crystal, molecules are linked through C-HO hydrogen bonds, forming polymeric chains in [100].

Related literature

For the preparation, see: Bouhfid et al. (2005). For a related structure and background to isatin derivatives, see: Liu et al. (2011). For reference bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₀ClNO₂
M_r = 271.69
Orthorhombic, P b c a
a = 22.864 (5) Å
b = 16.600 (3) Å
c = 13.335 (3) Å
V = 5061.2 (18) Å³
Z = 16
Mo K radiation
= 0.30 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.916, T_max = 0.971
4623 measured reflections
4623 independent reflections
1929 reflections with I > 2(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.117
S = 1.00
4623 reflections
343 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3AO1ⁱ	0.93	2.58	3.228 (4)	127
C4-H4AO2ⁱ	0.93	2.56	3.473 (4)	167
C18-H18AO3ⁱⁱ	0.93	2.40	3.329 (4)	173
C19-H19AO4ⁱⁱ	0.93	2.60	3.382 (6)	142
C26-H26AO2ⁱⁱⁱ	0.93	2.59	3.350 (4)	140
C29-H29AO1^iv	0.93	2.59	3.505 (5)	169
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6540 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

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.
Bouhfid, R., Joly, N., Massoui, M., Cecchelli, R., Lequart, V., Martin, P. & Essassi, E. M. (2005). Heterocycles, 65, 2949-2955.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Liu, H., Fan, D., Wang, D. & Ou-yang, P.-K. (2011). Acta Cryst. E67, o3427.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds