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Volume 69 
Part 9 
Page o1481  
September 2013  

Received 1 August 2013
Accepted 19 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
H completeness 99%
Disorder in solvent or counterion
R = 0.040
wR = 0.110
Data-to-parameter ratio = 15.1
Details
Open access

4'-(1H-Imidazol-2-yl)-3'-[(1H-indol-3-yl)carbonyl]-1'-methyl-2-oxospiro[indoline-3,2'-pyrrolidine]-3'-carbonitrile 0.15-hydrate

aSri Ram Engineering College, Chennai 602 024, India,bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C25H20N6O2·0.15H2O, the dihedral angles between the least-squares planes of the indole and pyrrolidine rings and between the oxindole and imidazole rings are 77.66 (7) and 45.31 (7)°, respectively. The pyrrolidine ring and the fused five-membered pyrrolidine ring of the oxindole moiety exhibit twisted conformations. The amide N atom is involved in both intra- and intermolecular hydrogen bonding, having a bifurcated character. The molecular structure is characterized by an intramolecular N-H...O hydrogen bond, which generates an S(7) ring motif while an intermolecular N-H...O hydrogen bond links the organic and solvent water molecules. In the crystal, N-H...N hydrogen bonds generate a zigzag chain running parallel to c-axis direction. The H atoms of the solvent water molecule were not located.

Related literature

For background to indole derivatives and their biological activity, see: Rudrangi et al. (2011[Rudrangi, S. R. S., Bontha, V. K., Manda, V. R. & Bethi, S. (2011). Asian J. Res. Chem. 4, 335-338.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For 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.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a related structure, see: Inglebert et al. (2013[Inglebert, S. A., Arun, Y., Sethusankar, K. & Perumal, P. T. (2013). Acta Cryst. E69, o1328-o1329.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20N6O2·0.15H2O

  • Mr = 439.17

  • Monoclinic, P 21 /n

  • a = 8.650 (5) Å

  • b = 16.952 (5) Å

  • c = 14.438 (5) Å

  • [beta] = 97.161 (5)°

  • V = 2100.6 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.977

  • 22198 measured reflections

  • 4819 independent reflections

  • 3757 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

  • wR(F2) = 0.110

  • S = 1.03

  • 4819 reflections

  • 320 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N5i 0.89 (1) 2.13 (1) 2.9889 (19) 164 (2)
N6-H6A...O1W 0.90 (1) 1.98 (2) 2.714 (8) 138 (2)
N6-H6A...O1 0.90 (1) 2.57 (2) 3.064 (2) 116 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 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: RK2411 ).


Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Inglebert, S. A., Arun, Y., Sethusankar, K. & Perumal, P. T. (2013). Acta Cryst. E69, o1328-o1329.  [CrossRef] [ChemPort] [details]
Rudrangi, S. R. S., Bontha, V. K., Manda, V. R. & Bethi, S. (2011). Asian J. Res. Chem. 4, 335-338.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1481  [ doi:10.1107/S1600536813023246 ]

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