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Volume 68 
Part 12 
Page o3306  
December 2012  

Received 26 October 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.097
Data-to-parameter ratio = 13.8
Details
Open access

2,3-Dihydro-1H-pyrrolo[1,2-a]indole-9-carbonitrile

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050, Johannesburg, South Africa
Correspondence e-mail: joseph.michael@wits.ac.za

The asymmetric unit of the title compound, C12H10N2, which may serve as a model for mitosenes, contains two independent molecules. The conformation of the five-membered rings in both molecules is envelope, with the central CH2-CH2-CH2 C atom at the flap in each case. In the crystal, they interact by a combination of weak C-H...N and [pi]-[pi] interactions [centroid-centroid distances = 3.616 (1) and 3.499 (1) Å] and C-H...[pi] contacts.

Related literature

For the synthesis of the title compound by intramolecular Heck reaction of [1-(2-bromophenyl)pyrrolidin-2-ylidene]-acetonitrile, see: Michael et al. (1993[Michael, J. P., Chang, S.-F. & Wilson, C. (1993). Tetrahedron Lett. 34, 8365-8368.]). For an alternative synthesis by cyclization of [2-(2-oxopyrrolidin-1-yl)phenyl]acetonitrile with sodium hydride, see: Verboom et al. (1986[Verboom, W., Orlemans, E. O. M., Berga, H. J., Scheltinga, H. W. & Reinhoudt, D. N. (1986). Tetrahedron, 42, 5053-5064.]). For background to mitosenes, see: Franck (1978[Franck, R. W. (1978). Fortschr. Chem. Org. Naturst. 38, 1-45.]); Kasai & Kono (1992[Kasai, M. & Kono, M. (1992). Synlett, pp. 778-790.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N2

  • Mr = 182.22

  • Triclinic, [P \overline 1]

  • a = 9.1383 (3) Å

  • b = 9.5340 (3) Å

  • c = 12.3138 (4) Å

  • [alpha] = 90.794 (2)°

  • [beta] = 90.528 (2)°

  • [gamma] = 116.272 (2)°

  • V = 961.78 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.50 × 0.45 × 0.30 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.963, Tmax = 0.978

  • 7592 measured reflections

  • 3498 independent reflections

  • 2809 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.097

  • S = 1.04

  • 3498 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C6A-C11A and C6B-C11B rings, respectively.

D-H...A D-H H...A D...A D-H...A
C1A-H1A1...N2B 0.99 2.68 3.338 (2) 124
C2A-H2A1...N2B 0.99 2.66 3.373 (2) 129
C3A-H3A2...N2Ai 0.99 2.66 3.634 (2) 168
C3B-H3B1...N2Bii 0.99 2.57 3.495 (2) 156
C3A-H3A1...Cg1iii 0.99 2.79 3.545 (2) 135
C3B-H3B2...Cg2iv 0.99 2.67 3.523 (2) 146
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x, -y, -z; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) 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: BH2462 ).


Acknowledgements

This work was supported by the University of the Witwatersrand and the Molecular Sciences Institute, which are thanked for providing the infrastructure required to do this work. Ms C. Wilson is thanked for carrying out the preliminary synthesis.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Franck, R. W. (1978). Fortschr. Chem. Org. Naturst. 38, 1-45.  [CrossRef]
Kasai, M. & Kono, M. (1992). Synlett, pp. 778-790.  [CrossRef]
Michael, J. P., Chang, S.-F. & Wilson, C. (1993). Tetrahedron Lett. 34, 8365-8368.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Verboom, W., Orlemans, E. O. M., Berga, H. J., Scheltinga, H. W. & Reinhoudt, D. N. (1986). Tetrahedron, 42, 5053-5064.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2012). E68, o3306  [ doi:10.1107/S1600536812045345 ]

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