[Journal logo]

Volume 69 
Part 4 
Pages o614-o615  
April 2013  

Received 27 February 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.042
wR = 0.114
Data-to-parameter ratio = 14.7
Details
Open access

5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione acetic acid hemisolvate

aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: najat_abbassi@hotmail.com

The molecular structure of the title compound, C28H22N2O6S2·0.5CH3COOH, is built up from three fused rings, two six and one eight membered. The eight-membered ring shows a boat conformation and the dihedral angle between the two benzene groups attached thereto is 66.43 (11)°, resulting in a V-shaped geometry. Two tosyl substituents are bound to the N atoms. The planes through the tolyl rings are roughly perpendicular, as indicated by the dihedral angle of 82.44 (12)°. In the crystal, the molecule and its inversion-related symmetry-equivalent are linked to the acetic acid solvent molecule by non-classical O-H...O and C-H...O hydrogen bonds. Two half-occupied acetic acid solvent molecules are disordered at the same site and linked by a center of symmetry.

Related literature

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010[Brzozowski, Z., S1awinski, J., Saczewski, F., Innocenti, A., Supuran, C. T. (2010). Eur. J. Med. Chem. 45, 2396-2404.]); Drew (2000[Drew, J. (2000). Science, 287, 1960-964.]); Garaj et al. (2005[Garaj, V., Puccetti, L., Fasolis, G., Winum, J. Y., Montero, J. L., Scozzafava, A., Vullo, D., Innocenti, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3102-3108.]). For their antiproliferative activity, see: Abbassi et al. (2012[Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240-249.]); Bouissane et al. (2006[Bouissane, L., El Kazzouli, S., Léonce, S., Pffeifer, P., Rakib, E. M., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.]); Lopez et al. (2010[Lopez, M., Bornaghi, L. F., Innocenti, A., Vullo, D., Charman, S. A., Supuran, C. T. & Poulsen, S.-A. (2010). J. Med. Chem. 53, 2913-2926.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C28H22N2O6S2·0.5C2H4O2

  • Mr = 576.62

  • Triclinic, [P \overline 1]

  • a = 8.6933 (11) Å

  • b = 11.1746 (18) Å

  • c = 14.8051 (19) Å

  • [alpha] = 87.042 (4)°

  • [beta] = 74.370 (5)°

  • [gamma] = 75.097 (4)°

  • V = 1338.2 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 296 K

  • 0.41 × 0.35 × 0.27 mm

Data collection
  • Bruker X8 APEX diffractometer

  • 19664 measured reflections

  • 5446 independent reflections

  • 4262 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.114

  • S = 1.02

  • 5446 reflections

  • 370 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O8-H8...O3 0.95 2.66 3.460 (3) 142
C30-H30C...O3i 0.96 2.71 3.473 (5) 136
C16-H16...O2 0.93 2.49 3.190 (3) 132
C11-H11...O4ii 0.93 2.54 3.241 (2) 133
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2423 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240-249.  [ISI] [CrossRef] [ChemPort] [PubMed]
Bouissane, L., El Kazzouli, S., Léonce, S., Pffeifer, P., Rakib, E. M., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078-1088.  [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Brzozowski, Z., S1awinski, J., Saczewski, F., Innocenti, A., Supuran, C. T. (2010). Eur. J. Med. Chem. 45, 2396-2404.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Drew, J. (2000). Science, 287, 1960-964.  [ISI] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Garaj, V., Puccetti, L., Fasolis, G., Winum, J. Y., Montero, J. L., Scozzafava, A., Vullo, D., Innocenti, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3102-3108.  [CrossRef] [PubMed] [ChemPort]
Lopez, M., Bornaghi, L. F., Innocenti, A., Vullo, D., Charman, S. A., Supuran, C. T. & Poulsen, S.-A. (2010). J. Med. Chem. 53, 2913-2926.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o614-o615   [ doi:10.1107/S1600536813007903 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.