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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 [sigma](C-C) = 0.006 Å
R = 0.064
wR = 0.117
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O hydrogen bonds, forming polymeric chains in [100].

Related literature

For the preparation, see: Bouhfid et al. (2005[Bouhfid, R., Joly, N., Massoui, M., Cecchelli, R., Lequart, V., Martin, P. & Essassi, E. M. (2005). Heterocycles, 65, 2949-2955.]). For a related structure and background to isatin derivatives, see: Liu et al. (2011[Liu, H., Fan, D., Wang, D. & Ou-yang, P.-K. (2011). Acta Cryst. E67, o3427.]). For reference bond-length data, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10ClNO2

  • Mr = 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[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.916, Tmax = 0.971

  • 4623 measured reflections

  • 4623 independent reflections

  • 1929 reflections with I > 2[sigma](I)

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.117

  • S = 1.00

  • 4623 reflections

  • 343 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...O1i 0.93 2.58 3.228 (4) 127
C4-H4A...O2i 0.93 2.56 3.473 (4) 167
C18-H18A...O3ii 0.93 2.40 3.329 (4) 173
C19-H19A...O4ii 0.93 2.60 3.382 (6) 142
C26-H26A...O2iii 0.93 2.59 3.350 (4) 140
C29-H29A...O1iv 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[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; 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: 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: 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.  [ChemPort]
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.  [CrossRef] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o37  [ doi:10.1107/S1600536811051816 ]

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