7α,15α-Dibromo-8,16-diphenyl-6,7,14,15-tetra­hydro-6α,14α-epithio­cyclo­octa­[1,2-b:5,6-b′]diquinoline deuterochloro­form solvate

Chan, I.Y.H.; Bishop, R.; Craig, D.C.; Bhadbhade, M.M.; Scudder, M.L.

doi:10.1107/S1600536809032978

Volume 65
Part 9
Page o2253
September 2009

Received 7 August 2009
Accepted 19 August 2009
Online 26 August 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
Disorder in solvent or counterion
R = 0.045
wR = 0.130
Data-to-parameter ratio = 13.2
Details

7,15-Dibromo-8,16-diphenyl-6,7,14,15-tetrahydro-6,14-epithiocycloocta[1,2-b:5,6-b']diquinoline deuterochloroform solvate

Isa Y. H. Chan,^a Roger Bishop,^a Donald C. Craig,^a Mohan M. Bhadbhade ^b and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney 2052, Australia, and ^bThe Analytical Centre, University of New South Wales, Sydney 2052, Australia
Correspondence e-mail: m.scudder@unsw.edu.au

In the racemic title compound, C₃₄H₂₂Br₂N₂S·CDCl₃, pairs of diquinoline host molecules form centrosymmetric brick-like dimers utilizing three different aryl edge-to-face interactions (EF_1-3). The dimeric (EF)₆ (i.e. 2 × EF_1-3) building blocks pack with the deuterochloroform guest molecules positioned near each of their corners. The Cl atoms of the latter are disordered over two sets of sites in a 0.53 (2):0.47 (2) ratio.

Related literature

The solvent-free C₃₄H₂₂Br₂N₂S molecule crystallizes in space group C2/c exhibiting a layer structure that does not contain (EF)₆ bricks (Alshahateet et al., 2008). These bricks are, however, present in five alternative inclusion crystal structures formed by the same host (Alshahateet et al., 2008). Similar dimeric (EF)₆ building blocks have also been found in crystal structures of other structurally related racemic diquinoline molecules (Ashmore et al., 2004, 2009).

Experimental

Crystal data

C₃₄H₂₂Br₂N₂S·CDCl₃
M_r = 770.81
Triclinic, $[P \overline 1]$
a = 10.161 (4) Å
b = 10.246 (5) Å
c = 15.868 (6) Å
= 93.88 (3)°
= 99.43 (3)°
= 92.50 (3)°
V = 1623.4 (12) Å³
Z = 2
Mo K radiation
= 2.84 mm^-1
T = 294 K
0.26 × 0.24 × 0.12 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: analytical (de Meulenaer & Tompa, 1965) T_min = 0.489, T_max = 0.712
5894 measured reflections
5692 independent reflections
4210 reflections with I > 2(I)
R_int = 0.032
1 standard reflections frequency: 30 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.130
S = 0.84
5692 reflections
432 parameters
436 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.50 e Å^-3
_min = -0.64 e Å^-3

Data collection: CAD-4 Manual (Schagen et al., 1989); cell refinement: CAD-4 Manual; data reduction: CAD-4 Manual; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CrystalMaker (CrystalMaker, 2005); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5037 ).

Acknowledgements

This research was supported by the Australian Research Council.

References

Alshahateet, S. F., Bishop, R., Craig, D. C., Kooli, F. & Scudder, M. L. (2008). CrystEngComm, 10, 297-305.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Ashmore, J., Bishop, R., Craig, D. C. & Scudder, M. L. (2004). CrystEngComm, 6, 618-622.
Ashmore, J., Bishop, R., Craig, D. C. & Scudder, M. L. (2009). Cryst. Growth Des. 9, 2742-2750.
CrystalMaker (2005). CrystalMaker. CrystalMaker Software Ltd, Yarnton, England. URL: www.CrystalMaker.co.uk.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Enraf-Nonius, Delft, The Netherlands.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds