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Volume 68 
Part 1 
Pages o1-o2  
January 2012  

Received 8 November 2011
Accepted 28 November 2011
Online 3 December 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 13.0
Details
Open access

5',11'-Dihydrodispiro[cyclohexane-1,6'-indolo[3,2-b]carbazole-12',1''-cyclohexane]

Ilia A. Guzei,a* Lara C. Spencer,a Eric Codnerb* and Joshua M. Boehmb

aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA, and bDepartment of Chemical and Biological Engineering, University of Wisconsin-Madison, 1415 Engineering Drive, Madison, WI 53706, USA
Correspondence e-mail: iguzei@chem.wisc.edu, codner@engr.wisc.edu

The title compound, C28H30N2, is a symmetrical 2:2 product from the condensation of indole and cyclohexanone. It is the only reported 5,11-dihydroindolo[3,2-b]carbazole compound in which the spiro atoms are quaternary C atoms. Crystals were grown by vapor diffusion in a three-zone electric furnace. The molecule resides on a crystallographic inversion center. The cyclohexyl rings are in a slightly distorted chair conformation, whereas the indole units and the spiro-carbons are coplanar within 0.014 Å.

Related literature

For condensations of indole with cyclohexanone that yield 1:1 or 1:2 products, see: Yadav et al. (2001[Yadav, J. S., Reddy, B. V. S., Murthy, C. S. V. R., Kumar, G. M. & Madan, C. (2001). Synthesis, 5, 783-787.]). For indole-ketone condensation by forming vinylindole followed by a Diels-Alder reaction, see: Noland et al. (1993[Noland, W. E., Wahlstrom, M. J., Konkel, M. J., Brigham, M. E., Trowbridge, A. G., Konkel, L. M. C., Gourneau, R. P., Scholten, C. A., Lee, N. H., Condolucci, J. J., Gac, T. S., Pour, M. M. & Radford, P. M. (1993). J. Heterocycl. Chem. 30, 81-91.]). Recrystallization by the vapor-phase diffusion approach is explained in Kloc et al. (1997[Kloc, C., Simpkins, P. G., Siegrist, T. & Laudise, R. A. (1997). J. Cryst. Growth, 182, 416-427.]). For information on the related compound trans-6,12-diphenyl-5,6,11,12-tetrahydroindolo[3,2-b]carbazole dimethyl sulfoxide tetrahydrofuran solvate, see: Gu et al. (2009[Gu, R., Van Snick, S., Robeyns, K., Van Meervelt, L. & Dehaen, W. (2009). Org. Biomol. Chem. 7, 380-385.]). Related compounds were found in the Cambridge Structural Database (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). Geometrical parameters were analyzed using Mogul (Bruno et al., 2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]).

[Scheme 1]

Experimental

Crystal data

  • C28H30N2

  • Mr = 394.54

  • Monoclinic, P 21 /c

  • a = 7.4655 (2) Å

  • b = 13.6820 (4) Å

  • c = 10.5348 (3) Å

  • [beta] = 109.380 (1)°

  • V = 1015.08 (5) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.57 mm-1

  • T = 100 K

  • 0.38 × 0.30 × 0.19 mm
Data collection

  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: analytical (SADABS; Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.813, Tmax = 0.900

  • 20619 measured reflections

  • 1826 independent reflections

  • 1779 reflections with I > 2[sigma](I)

  • Rint = 0.022
Refinement

  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.113

  • S = 0.99

  • 1826 reflections

  • 140 parameters

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Selected geometric parameters (Å, °)

N1-C1 1.3743 (16)
N1-C8 1.3872 (16)
C1-N1-C8 109.12 (11)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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, FCF_filter (Guzei, 2007[Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]) and INSerter (Guzei, 2007[Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]); molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and modiCIFer (Guzei, 2007[Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2127 ).

Acknowledgements

EC thanks Professor Wayland E. Noland for his assistance in initiating this project.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.  [ISI] [CrossRef] [details]
Gu, R., Van Snick, S., Robeyns, K., Van Meervelt, L. & Dehaen, W. (2009). Org. Biomol. Chem. 7, 380-385.  [CSD] [CrossRef] [PubMed] [ChemPort]
Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.
Kloc, C., Simpkins, P. G., Siegrist, T. & Laudise, R. A. (1997). J. Cryst. Growth, 182, 416-427.  [ISI] [CrossRef] [ChemPort]
Noland, W. E., Wahlstrom, M. J., Konkel, M. J., Brigham, M. E., Trowbridge, A. G., Konkel, L. M. C., Gourneau, R. P., Scholten, C. A., Lee, N. H., Condolucci, J. J., Gac, T. S., Pour, M. M. & Radford, P. M. (1993). J. Heterocycl. Chem. 30, 81-91.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yadav, J. S., Reddy, B. V. S., Murthy, C. S. V. R., Kumar, G. M. & Madan, C. (2001). Synthesis, 5, 783-787.  [CrossRef]

Acta Cryst (2012). E68, o1-o2   [ doi:10.1107/S1600536811051208 ]

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