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Volume 64 
Part 1 
Page o48  
January 2008  

Received 18 November 2007
Accepted 20 November 2007
Online 6 December 2007


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© International Union of Crystallography 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.006 Å
R = 0.050
wR = 0.053
Data-to-parameter ratio = 5.4
Details

2,3,10,11-Tetramethoxy-6,7,14,15-tetrahydro-6,14-methanocycloocta[1,2-b;5,6-b']diquinoline

Jason Ashmore,a Roger Bishop,a* Donald C. Craiga and Marcia L. Scuddera

aSchool of Chemistry, University of New South Wales, Sydney, Australia 2052
Correspondence e-mail: r.bishop@unsw.edu.au

The racemic title compound, C27H26N2O4, crystallizes with its central carbon bridge on a twofold axis. It forms parallel chains of molecules utilizing aryl offset face-face interactions with an interplanar distance of about 3.5 Å. These chains associate further by means of pairs of O-CH2-H...[pi] (with H-ring distances ranging from 2.69 to 2.95 Å) and O-CH2-H...N motifs. The methoxy groups in this structure are coplanar with the aromatic rings to which they are attached. This is recognized as being common behaviour amongst aromatic methoxy compounds.

Related literature

Condensation of two equivalents of a 2-aminobenzaldehyde derivative with one of bicyclo[3.3.1]nonane-2,6-dione provides a V-shaped diquinoline adduct by means of the Friedländer condensation (Cheng & Yan, 1982[Cheng, C.-C. & Yan, S.-J. (1982). Org. React. 28, 37-201.]). Substituted molecules of this general structural type frequently act as lattice inclusion hosts (Bishop, 2006[Bishop, R. (2006). Crystal Engineering of Halogenated Heteroaromatic Clathrate Systems. In Frontiers in Crystal Engineering, ch. 5, pp. 91-116, edited by E. R. T. Tiekink & J. J. Vittal. Chichester: Wiley.]). For related literature, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Desiraju & Gavezzotti (1989[Desiraju, G. R. & Gavezzotti, A. (1989). Acta Cryst. B45, 473-482.]); Marjo et al. (1997[Marjo, C. E., Scudder, M. L., Craig, D. C. & Bishop, R. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 2099-2104.]); Pendrak et al. (1995[Pendrak, I., Wittrock, R. & Kingsbury, W. D. (1995). J. Org. Chem. 60, 2912-2915.]); Schaefer & Honig (1968[Schaefer, J. P. & Honig, L. M. (1968). J. Org. Chem. 33, 2655-2659.]).

[Scheme 1]

Experimental

Crystal data

  • C27H26N2O4

  • Mr = 442.5

  • Monoclinic, C 2/c

  • a = 14.137 (7) Å

  • b = 9.533 (6) Å

  • c = 16.551 (7) Å

  • [beta] = 100.79 (3)°

  • V = 2191 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 294 K

  • 0.12 mm (radius)
Data collection

  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 1999 measured reflections

  • 1926 independent reflections

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

  • Rint = 0.062

  • 1 standard reflection frequency: 30 min intensity decay: none
Refinement

  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.053

  • S = 1.41

  • 803 reflections

  • 150 parameters

  • H-atom parameters not refined

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H3C14...N1i 1.00 2.88 3.723 (5) 142
C14-H3C14...N1ii 1.00 2.96 3.348 (5) 104
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CAD-4 Software (Schagen et al., 1989[Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Software. Version 5.0. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: Local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: RAELS (Rae, 2000[Rae, A. D. (2000). RAELS. Australian National University, Canberra.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII, Oak Ridge National Laboratory, Tennessee, USA.]) and CrystalMaker (CrystalMaker, 2005[CrystalMaker (2005). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England. http://www.crystalmaker.co.uk .]); software used to prepare material for publication: Local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LN2008 ).

Acknowledgements

This research was supported by the UNSW Faculty Research Grants Program.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [CrossRef] [details]
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Bishop, R. (2006). Crystal Engineering of Halogenated Heteroaromatic Clathrate Systems. In Frontiers in Crystal Engineering, ch. 5, pp. 91-116, edited by E. R. T. Tiekink & J. J. Vittal. Chichester: Wiley.
Cheng, C.-C. & Yan, S.-J. (1982). Org. React. 28, 37-201.  [ChemPort]
CrystalMaker (2005). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England. http://www.crystalmaker.co.uk .
Desiraju, G. R. & Gavezzotti, A. (1989). Acta Cryst. B45, 473-482.  [CrossRef] [details]
Johnson, C. K. (1976). ORTEPII, Oak Ridge National Laboratory, Tennessee, USA.
Marjo, C. E., Scudder, M. L., Craig, D. C. & Bishop, R. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 2099-2104.
Pendrak, I., Wittrock, R. & Kingsbury, W. D. (1995). J. Org. Chem. 60, 2912-2915.  [CrossRef] [ChemPort]
Rae, A. D. (2000). RAELS. Australian National University, Canberra.  [CrossRef] [ChemPort]
Schaefer, J. P. & Honig, L. M. (1968). J. Org. Chem. 33, 2655-2659.  [CrossRef] [ChemPort]
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Software. Version 5.0. Enraf-Nonius, Delft, The Netherlands.

Acta Cryst (2008). E64, o48  [ doi:10.1107/S1600536807061235 ]