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Volume 64 
Part 2 
Page o425  
February 2008  

Received 21 November 2007
Accepted 7 January 2008
Online 11 January 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.043
wR = 0.122
Data-to-parameter ratio = 41.0
Details
Open access

3-Ethyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo[3,4-b]quinoline

aDepartment of Physics, Anna University, Chennai 600 025, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: kali@annauniv.edu, hkfun@usm.my

In the molecule of the title compound, C26H28N2O2S, the pyrrolidine ring adopts an envelope conformation and the tetrahydropyridine ring is in a half-chair conformation; these two rings are trans-fused. The dihedral angle between the pyridine- and sulfonyl-bound benzene rings is 36.15 (5)°. In the crystalline state, the molecules are linked into a two-dimensional network parallel to the ab plane by C-H...O and C-H...[pi] interactions.

Related literature

For the orientations of phenyl and ethyl substituents with respect to the fused ring system in the related 7-chloro- and 7-bromo-derivatives, see: Sudha et al. (2007[Sudha, D., Chinnakali, K., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2007). Acta Cryst. E63, o4914-o4915.], 2008[Sudha, D., Chinnakali, K., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2008). Acta Cryst. E64, o134.]). For biological activities of pyrrolo[3,4-b]quinoline derivatives, see: Anzini et al. (1990[Anzini, M., Cappelli, A., Vomero, S., Botta, M. & Cagnotto, A. (1990). Il Farmaco, 45, 1169-1179.], 1992[Anzini, M., Cappelli, A., Vomero, S., Cagnotto, A. & Skorupska, M. (1992). Il Farmaco, 47, 191-202.]); Crenshaw et al. (1976[Crenshaw, R. R., Luke, G. M. & Siminoff, P. (1976). J. Med. Chem. 19, 262-275.]); Fujita et al. (1996[Fujita, M., Egawa, H., Miyamoto, T., Nakano, J. & Matsumoto, J. (1996). Eur. J. Med. Chem. 31, 981-988.]); Xiao et al. (2006[Xiao, X.-S., Antony, S., Pommier, Y. & Cushman, M. (2006). J. Med. Chem. 49, 1408-1412.]). For related literature, see: Duax et al. (1976[Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. Allinger, pp. 271-383. New York: Wiley.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28N2O2S

  • Mr = 432.56

  • Triclinic, [P \overline 1]

  • a = 9.3990 (1) Å

  • b = 10.9077 (2) Å

  • c = 12.5654 (3) Å

  • [alpha] = 64.3190 (8)°

  • [beta] = 72.5291 (8)°

  • [gamma] = 76.3803 (8)°

  • V = 1099.07 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 100.0 (1) K

  • 0.48 × 0.37 × 0.17 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.878, Tmax = 0.971

  • 49024 measured reflections

  • 11697 independent reflections

  • 9445 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.122

  • S = 1.03

  • 11697 reflections

  • 285 parameters

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

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C4-C9, C12-C17 and C19-C24 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C8-H8...O1i 0.93 2.40 3.3215 (13) 171
C23-H23...O2ii 0.93 2.53 3.2821 (13) 138
C2-H2...Cg1 0.98 2.94 3.8269 (9) 151
C7-H7...Cg3i 0.93 2.95 3.7883 (12) 151
C10-H10...Cg2iii 0.98 2.83 3.8072 (9) 178
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Version 5.1; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2188 ).


Acknowledgements

HKF thanks Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS), grant No. 203/PFIZIK/671064.

References

Anzini, M., Cappelli, A., Vomero, S., Botta, M. & Cagnotto, A. (1990). Il Farmaco, 45, 1169-1179.  [PubMed] [ChemPort]
Anzini, M., Cappelli, A., Vomero, S., Cagnotto, A. & Skorupska, M. (1992). Il Farmaco, 47, 191-202.  [PubMed] [ChemPort]
Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Crenshaw, R. R., Luke, G. M. & Siminoff, P. (1976). J. Med. Chem. 19, 262-275.  [CrossRef] [PubMed] [ChemPort] [ISI]
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. Allinger, pp. 271-383. New York: Wiley.
Fujita, M., Egawa, H., Miyamoto, T., Nakano, J. & Matsumoto, J. (1996). Eur. J. Med. Chem. 31, 981-988.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [CrossRef] [details]
Sudha, D., Chinnakali, K., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2007). Acta Cryst. E63, o4914-o4915.  [CSD] [CrossRef] [details]
Sudha, D., Chinnakali, K., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2008). Acta Cryst. E64, o134.  [CrossRef] [details]
Xiao, X.-S., Antony, S., Pommier, Y. & Cushman, M. (2006). J. Med. Chem. 49, 1408-1412.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2008). E64, o425  [ doi:10.1107/S1600536808000482 ]