4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)meth­yl]-N′-[(E)-4-nitro­benzyl­idene]benzene­sulfono­hydrazide dimethyl sulfoxide monosolvate

Bortoluzzi, A.J.; Policarpi, E.B.; Mora, C.; Oliveira, K.N.; Nunes, R.J.

doi:10.1107/S1600536811004697

Volume 67
Part 3
Pages o627-o628
March 2011

Received 21 January 2011
Accepted 7 February 2011
Online 12 February 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.052
wR = 0.163
Data-to-parameter ratio = 12.8
Details

4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]-N'-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide dimethyl sulfoxide monosolvate

Adailton J. Bortoluzzi,^a ^* Everton B. Policarpi,^a Cristiano Mora,^a Kely N. Oliveira ^a and Ricardo J. Nunes ^a

^aDepartamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis, Brazil
Correspondence e-mail: adajb@qmc.ufsc.br

The molecular structure of the title compound, C₂₆H₁₈N₄O₆S·C₂H₆OS, shows an E conformation of the hydrazone double bond. The presence of a methylene group between the benzo[de]isoquinoline and benzenesulfonyl moieties allows the 4-nitrophenyl ring and the benzo[de]isoquinoline system to be parallel with respect to each other, so that the molecule adopts a U-shaped spatial conformation. The dihedral angle between mean planes of these aromatic groups is 4.4 (1)°. This special arrangement enables neighboring molecules to be intercalated, forming slipped [pi] - [pi] interactions [centroid-centroid distance = 3.535 (2) Å] between the 4-nitrophenyl and benzo[de]isoquinoline groups and point-to-face C-H [pi] interactions between the benzo[de]isoquinoline and benzenesulfonyl aromatic systems. In addition, the crystal packing also features an intermolecular N-HO interaction involving the amine group and the dimethyl sulfoxide solvent molecule.

Related literature

For the therapeutic properties of sulfonylhydrazones, see: Rollas et al. (2002); Frlan et al. (2008); Lima et al. (1999); Sondhi et al. (2006) and for their biological activity, see: Kendall et al. (2007); Sadek et al. (2008). For the anticancer activity of naphthalimides, see: Braña & Ramos (2001); Braña et al. (2001); Suárez & Sánchez (1992); Ingrassia et al. (2009); Wu et al. (2009); Norton et al. (2008). For the therapeutic properties of cyclic imides, see: Cechinel Filho et al. (2003); Walter et al. (2002). For background to this study, see: Silva et al. (2006); Oliveira & Nunes (2006).

Experimental

Crystal data

C₂₆H₁₈N₄O₆S·C₂H₆OS
M_r = 592.63
Triclinic, $[P \overline 1]$
a = 9.152 (1) Å
b = 11.971 (1) Å
c = 13.910 (1) Å
= 107.268 (7)°
= 101.789 (7)°
= 96.319 (8)°
V = 1400.6 (2) Å³
Z = 2
Mo K radiation
= 0.24 mm^-1
T = 293 K
0.50 × 0.16 × 0.13 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
5055 measured reflections
4737 independent reflections
3075 reflections with I > 2(I)
R_int = 0.017
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.163
S = 1.04
4737 reflections
371 parameters
H-atom parameters constrained
_max = 0.73 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the p-nitrophenyl (C22-C27) ring.

D-HA	D-H	HA	DA	D-HA
N2-H2NO1S	0.80	1.99	2.764 (4)	163
C8-H8Cgⁱ	0.93	2.90	3.799 (6)	162
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2001 ).

Acknowledgements

The authors thank CAPES and CNPq for financial support.

References

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organic compounds