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Volume 69 
Part 10 
Page o1585  
October 2013  

Received 6 September 2013
Accepted 19 September 2013
Online 25 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.073
wR = 0.252
Data-to-parameter ratio = 17.3
Details
Open access

3'-[(1H-Indol-3-yl)carbonyl]-1'-methyl-2-oxo-4'-(thiophen-2-yl)spiro[indoline-3,2'-pyrrolidine]-3'-carbonitrile

aSri Ram Engineering College, Chennai 602 024, India,bOrganic Chemistry Division, CSIR Central Leather Research Institute, 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, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thiophene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N-H...O hydrogen bonds link the molecules, forming inversion dimers with an R22(8) ring motif. The dimers are linked by further N-H...O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

Related literature

For background to indole derivatives and their biological activity, see: Srivastava et al. (2011[Srivastava, Anupam & Pandeya, S. N. (2011). JCPR, 1, 1-17.]). 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
  • C26H20N4O2S

  • Mr = 452.52

  • Monoclinic, P 21 /c

  • a = 11.6215 (6) Å

  • b = 17.1050 (11) Å

  • c = 12.3381 (8) Å

  • [beta] = 114.431 (2)°

  • V = 2233.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker APEXII2 CCD difractometer diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.941, Tmax = 0.957

  • 16319 measured reflections

  • 5279 independent reflections

  • 3636 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.252

  • S = 1.07

  • 5279 reflections

  • 306 parameters

  • 5 restraints

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

  • [Delta][rho]max = 1.15 e Å-3

  • [Delta][rho]min = -0.98 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O2i 0.84 (4) 2.12 (5) 2.828 (3) 142 (5)
N4-H4A...O1ii 0.85 (3) 1.99 (3) 2.829 (3) 177 (3)
Symmetry codes: (i) -x+1, -y, -z; (ii) [x, -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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: SU2642 ).


Acknowledgements

The authors are gratefully to 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] [Web of Science]
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] [Web of Science]
Inglebert, S. A., Arun, Y., Sethusankar, K. & Perumal, P. T. (2013). Acta Cryst. E69, o1328-o1329.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Srivastava, Anupam & Pandeya, S. N. (2011). JCPR, 1, 1-17.


Acta Cryst (2013). E69, o1585  [ doi:10.1107/S1600536813025890 ]

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