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

Madeley, L.G.; Lemmerer, A.; Michael, J.P.

doi:10.1107/S1600536812045345

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.097
Data-to-parameter ratio = 13.8
Details

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

Lee G. Madeley,^a Andreas Lemmerer ^a and Joseph P. Michael ^a ^*

^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-HN 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). For an alternative synthesis by cyclization of [2-(2-oxopyrrolidin-1-yl)phenyl]acetonitrile with sodium hydride, see: Verboom et al. (1986). For background to mitosenes, see: Franck (1978); Kasai & Kono (1992).

Experimental

Crystal data

C₁₂H₁₀N₂
M_r = 182.22
Triclinic, $[P \overline 1]$
a = 9.1383 (3) Å
b = 9.5340 (3) Å
c = 12.3138 (4) Å
= 90.794 (2)°
= 90.528 (2)°
= 116.272 (2)°
V = 961.78 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.963, T_max = 0.978
7592 measured reflections
3498 independent reflections
2809 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.097
S = 1.04
3498 reflections
254 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C1A-H1A1N2B	0.99	2.68	3.338 (2)	124
C2A-H2A1N2B	0.99	2.66	3.373 (2)	129
C3A-H3A2N2Aⁱ	0.99	2.66	3.634 (2)	168
C3B-H3B1N2Bⁱⁱ	0.99	2.57	3.495 (2)	156
C3A-H3A1Cg1ⁱⁱⁱ	0.99	2.79	3.545 (2)	135
C3B-H3B2Cg2^iv	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); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Franck, R. W. (1978). Fortschr. Chem. Org. Naturst. 38, 1-45.
Kasai, M. & Kono, M. (1992). Synlett, pp. 778-790.
Michael, J. P., Chang, S.-F. & Wilson, C. (1993). Tetrahedron Lett. 34, 8365-8368.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Verboom, W., Orlemans, E. O. M., Berga, H. J., Scheltinga, H. W. & Reinhoudt, D. N. (1986). Tetrahedron, 42, 5053-5064.

organic compounds