1-[4-({4-[(E)-(2-Hy­droxy­naphthalen-1-yl)methyl­idene­amino]­phen­yl}sulfan­yl)phen­yl]ethanone

Hebbachi, R.; Mousser, H.; Mousser, A.

doi:10.1107/S1600536812049835

Volume 69
Part 1
Pages o67-o68
January 2013

Received 30 November 2012
Accepted 5 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.046
wR = 0.125
Data-to-parameter ratio = 14.0
Details

1-[4-({4-[(E)-(2-Hydroxynaphthalen-1-yl)methylideneamino]phenyl}sulfanyl)phenyl]ethanone

Rabihe Hebbachi,^a Hénia Mousser ^b ^* and Abdelhamid Mousser ^a

^aDépartement de Chimie, Faculté des Sciences Exactes, Université Mentouri Constantine, Route de Ain El Bey, Constantine, Algerie, and ^bDépartement de Chimie Industrielle, Faculté des Sciences de l'Ingénieur, Université Mentouri Constantine, Campus Chaab Erssas, Constantine, Algerie
Correspondence e-mail: abmousser@yahoo.fr

The title Schiff base compound, C₂₅H₁₉NO₂S, crystallizes in a statistically disordered structure comprising keto and enol tautomeric forms. In the enol form, the benzenoid arrangment is promoted by a strong intramolecular O-HN hydrogen bond and adopts an E conformation about the imine bond. In the keto form there is an intramolecular N-HO hydrogen bond. In the crystal, an extended network of C-HO hydrogen bonds stabilizes columns parallel to the c axis, forming large voids (there are four cavities of 108 Å³ per unit cell) with highly disordered residual electron density. The SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148-155] was used to eliminate the contribution of this electron density from the intensity data, and the solvent-free model was employed for the final refinement. The contribution of this undetermined solvent was ignored in the calculation of the unit-cell characteristics.

Related literature

For related structures, see: Blagus & Kaitner (2011); Farag et al. (2010); Venkatachalam et al. (2011). For background to Schiff bases and their applications, see: Li et al. (2003); Villar et al. (2004); Kagkelari et al. (2009); Ourari et al. (2008); Zidane et al. (2011).

Experimental

Crystal data

C₂₅H₁₉NO₂S
M_r = 397.47
Monoclinic, C c
a = 10.695 (3) Å
b = 44.458 (14) Å
c = 4.4437 (11) Å
= 99.004 (9)°
V = 2086.8 (10) Å³
Z = 4
Mo K radiation
= 0.18 mm^-1
T = 150 K
0.58 × 0.17 × 0.06 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.898, T_max = 0.990
8026 measured reflections
3680 independent reflections
2952 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.125
S = 0.98
3680 reflections
263 parameters
2 restraints
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 1291 Friedel pairs
Flack parameter: -0.06 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H1AN13A	0.84	1.80	2.558 (4)	149
N13B-H13BO1B	0.88	1.85	2.558 (4)	136
C9-H9O28ⁱ	0.95	2.46 (1)	3.398 (4)	168
C19A-H19AO28ⁱ	0.95	2.56 (1)	3.506 (4)	174
C22-H22O1Aⁱⁱ	0.95	2.44 (1)	3.337 (4)	157
C27-H27BO1Aⁱ	0.98	2.49 (1)	3.442 (4)	164
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5178 ).

Acknowledgements

The authors thank Dr Lahcène Ouahab and Thierry Roisnel from the Institut des Sciences Chimiques de Rennes UMR CNRS 6226 for the data collection and helpful discussions, and the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Blagus, A. & Kaitner, B. (2011). Acta Cryst. E67, o2958-o2959.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farag, A. M., Teoh, S. G., Osman, H., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o1227-o1228.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Kagkelari, A., Papaefstahiou, G. S., Raptopoulou, C. P. & Zafiropoulos, T. F. (2009). Polyhedron, 28, 3279-3283.
Li, Y., Yang, Z. S., Zhang, H., Cao, B. J. & Wang, F. D. (2003). Bioorg. Med. Chem. 11, 4363-4368.
Ourari, A., Ouari, K., Khan, M. A. & Bouet, G. (2008). J. Coord. Chem. 61, 3846-3859.
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Venkatachalam, T. K., Pierens, G. K., Bernhardt, P. V., Hammond, L. & Reutens, D. C. (2011). J. Chem. Crystallogr. 41, 944-951.
Villar, R., Encio, I., Migliaccio, M., Gil, M. G. & Martinez-Merino, V. (2004). Bioorg. Med. Chem. 12, 963-968.
Zidane, Y., Ourari, A., Mousser, H. & Mousser, A. (2011). Acta Cryst. E67, m1069-m1070.

organic compounds