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Volume 66 
Part 4 
Pages o737-o738  
April 2010  

Received 23 February 2010
Accepted 25 February 2010
Online 3 March 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
Disorder in main residue
R = 0.045
wR = 0.126
Data-to-parameter ratio = 22.1
Details
Open access

Methyl 2-acetamido-2-(1-acetyl-3-hydroxy-2-oxoindolin-3-yl)propanoate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China.
Correspondence e-mail: hkfun@usm.my

In the title isatin compound, C16H18N2O6, the pyrrolidine ring adopts an envelope conformation and is inclined at a dihedral angle of 7.31 (5)° with respect to the benzene ring. The acetyl group is disordered over two positions with refined occupancies of 0.503 (4) and 0.497 (4). These groups make dihedral angles of 12.6 (6) and 19.6 (7)° with the pyrrolidine ring. In the crystal structure, intermolecular C-H...O hydrogen bonds link neighbouring molecules into infinite chains along the b axis. These chains are further interconnected by intermolecular O-H...O hydrogen bonds into two-dimensional arrays parallel to the bc plane. Weak intermolecular C-H...[pi] interactions further stabilize the crystal structure.

Related literature

For general background to and applications of isatin derivatives, see: Chu et al. (2007[Chu, W., Rothfuss, J., d'Avignon, A., Zeng, C., Zhou, D., Hotchkiss, R. S. & Mach, R. H. (2007). J. Med. Chem. 50, 3751-3755.]); Glover & Bhattacharya (1991[Glover, V. & Bhattacharya, S. K. (1991). Indian J. Exp. Biol. 29, 1-5.]); Gursoy & Karali (1996[Gursoy, A. & Karali, N. (1996). Farmaco, 51, 437-442.]); Pandeya et al. (1998[Pandeya, S. N., Sriram, D., Clercq, E. D., Pannecouque, C. & Witvrouw, M. (1998). Indian J. Pharm. Sci. 60, 207-212.]); Patel et al. (2006[Patel, A., Bari, S., Talele, G., Patel, J. & Sarangapani, M. (2006). Iranian J. Pharm. Res. 4, 249-254.]); Popp (1975[Popp, F. D. (1975). Adv. Heterocycl. Chem. 18, 1-58.]); Shvekhgeimer (1996[Shvekhgeimer, M.-G. A. (1996). Chem. Heterocycl. Compd, 345, 291-323.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P. & Meena, K. (2006). Pharmazie, 61, 274-277.]); Verma et al. (2004[Verma, M., Pandeya, S. N., Singh, K. N. & Stables, J. P. (2004). Acta Pharm. 54, 49-56.]); Vine et al. (2007[Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremmer, J. B. (2007). J. Med. Chem. 50, 5109-5117.]). For photoreactions of N-acetylisatin, see: Zhang et al. (2004[Zhang, Y., Wang, L., Zhang, M., Fun, H.-K. & Xu, J.-H. (2004). Org. Lett. 6, 4893-4893.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Usman et al. (2001[Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhang, Y. & Xu, J.-H. (2001). Acta Cryst. E57, o1070-o1072.], 2002a[Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhang, Y. & Xu, J.-H. (2002a). Acta Cryst. E58, o37-o39.],b[Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhao, B.-G. & Xu, J.-H. (2002b). Acta Cryst. C58, o24-o25.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18N2O6

  • Mr = 334.32

  • Monoclinic, C 2/c

  • a = 28.4345 (6) Å

  • b = 8.3396 (2) Å

  • c = 14.3779 (3) Å

  • [beta] = 114.351 (2)°

  • V = 3106.15 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.47 × 0.37 × 0.26 mm

Data collection
  • Bruker SMART APEX Duo CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.972

  • 39997 measured reflections

  • 5705 independent reflections

  • 4854 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.126

  • S = 1.03

  • 5705 reflections

  • 258 parameters

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

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O6i 0.875 (17) 1.769 (17) 2.6391 (10) 172 (2)
C3-H3A...O1ii 0.93 2.58 3.4098 (12) 150
C15-H15C...Cg1iii 0.96 2.96 3.9104 (11) 169
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) x, y-1, z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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: SJ2735 ).


Acknowledgements

Financial support from the Fok Ying Tung Education Foundation (114012) is acknowledged. HKF and JHG thank Universiti Sains Malaysia (USM) for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chu, W., Rothfuss, J., d'Avignon, A., Zeng, C., Zhou, D., Hotchkiss, R. S. & Mach, R. H. (2007). J. Med. Chem. 50, 3751-3755.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Glover, V. & Bhattacharya, S. K. (1991). Indian J. Exp. Biol. 29, 1-5.  [PubMed] [ChemPort]
Gursoy, A. & Karali, N. (1996). Farmaco, 51, 437-442.  [ChemPort] [PubMed]
Pandeya, S. N., Sriram, D., Clercq, E. D., Pannecouque, C. & Witvrouw, M. (1998). Indian J. Pharm. Sci. 60, 207-212.  [ChemPort]
Patel, A., Bari, S., Talele, G., Patel, J. & Sarangapani, M. (2006). Iranian J. Pharm. Res. 4, 249-254.
Popp, F. D. (1975). Adv. Heterocycl. Chem. 18, 1-58.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shvekhgeimer, M.-G. A. (1996). Chem. Heterocycl. Compd, 345, 291-323.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sriram, D., Yogeeswari, P. & Meena, K. (2006). Pharmazie, 61, 274-277.  [PubMed] [ChemPort]
Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhang, Y. & Xu, J.-H. (2001). Acta Cryst. E57, o1070-o1072.  [CSD] [CrossRef] [details]
Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhang, Y. & Xu, J.-H. (2002a). Acta Cryst. E58, o37-o39.  [CSD] [CrossRef] [details]
Usman, A., Razak, I. A., Fun, H.-K., Chantrapromma, S., Zhao, B.-G. & Xu, J.-H. (2002b). Acta Cryst. C58, o24-o25.  [CSD] [CrossRef] [details]
Verma, M., Pandeya, S. N., Singh, K. N. & Stables, J. P. (2004). Acta Pharm. 54, 49-56.  [PubMed] [ChemPort]
Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremmer, J. B. (2007). J. Med. Chem. 50, 5109-5117.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhang, Y., Wang, L., Zhang, M., Fun, H.-K. & Xu, J.-H. (2004). Org. Lett. 6, 4893-4893.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2010). E66, o737-o738   [ doi:10.1107/S1600536810007270 ]

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