(2E,2′E)-1,1′-Bis(6-chloro-2-methyl-4-phenyl­quinolin-3-yl)-3,3′-(1,4-phenyl­ene)diprop-2-en-1-one ethyl acetate disolvate

Kedjadja, A.; Merdes, R.; Bouacida, S.; Roisnel, T.; Belfaitah, A.

doi:10.1107/S1600536812049422

Volume 69
Part 1
Pages o37-o38
January 2013

Received 28 November 2012
Accepted 2 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.140
Data-to-parameter ratio = 17.2
Details

(2E,2'E)-1,1'-Bis(6-chloro-2-methyl-4-phenylquinolin-3-yl)-3,3'-(1,4-phenylene)diprop-2-en-1-one ethyl acetate disolvate

Allaoua Kedjadja,^a Rachid Merdes,^a Sofiane Bouacida,^b ^*⁺ Thierry Roisnel ^c and Ali Belfaitah ^d

^aLaboratoire de Chimie Appliquée, Faculté des Sciences, Université de Guelma 24000, Algeria,^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria,^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France, and ^dLaboratoire des Produits Naturels, d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title solvate, C₄₄H₃₀Cl₂N₂O₂·2C₄H₈O₂, the complete polycyclic molecule is generated by inversion symmetry. The dihedral angle between the quinolyl ring system (Q; r.m.s. deviation = 0.020 Å) and the pendant phenyl ring is 78.80 (6)°; the dihedral angle between Q and the central benzene ring is 85.92 (7)°. In the crystal, the components are linked by C-HO and C-H [pi] interactions, generating (110) layers. Weak aromatic [pi] - [pi] stacking [centroid-centroid distances = 3.7025 (11) and 3.8124 (10) Å] is also observed.

Related literature

For our previous studies in the area of potentially bioactive molecules, see: Menasra et al. (2005); Kedjadja et al. (2004). For further synthetic details, see: Wang et al. (2006).

Experimental

Crystal data

C₄₄H₃₀Cl₂N₂O₂·2C₄H₈O₂
M_r = 865.81
Triclinic, $[P \overline 1]$
a = 9.9851 (3) Å
b = 10.0086 (2) Å
c = 11.3676 (3) Å
= 102.350 (1)°
= 97.108 (1)°
= 95.290 (2)°
V = 1092.94 (5) Å³
Z = 1
Mo K radiation
= 0.20 mm^-1
T = 150 K
0.25 × 0.15 × 0.1 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.884, T_max = 0.980
18119 measured reflections
4866 independent reflections
4035 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.140
S = 1.04
4866 reflections
283 parameters
H-atom parameters constrained
_max = 1.02 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12-C17 ring.

D-HA	D-H	HA	DA	D-HA
C13-H13O19ⁱ	0.95	2.54	3.218 (2)	128
C23-H23O53	0.95	2.57	3.468 (2)	157
C24-H24O56ⁱⁱ	0.95	2.48	3.410 (3)	165
C51-H51BCg1ⁱⁱⁱ	0.98	2.76	3.627 (3)	147
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); 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: HB7004 ).

Acknowledgements

We are grateful to all personnel of the research squad "Synthèse de molécules à objectif thérapeutique" of the PHYSYNOR Laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are also due to the MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

References

Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kedjadja, A., Moussaoui, F., Debache, A., Rhouati, S. & Belfaitah, A. (2004). J. Soc. Alger. Chim. 14, 225-233.
Menasra, H., Kedjadja, A., Debache, A., Rhouati, S., Carboni, B. & Belfaitah, A. (2005). Synth. Commun. 35, 2779-2788.
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, G.-W., Jia, C.-C. & Dong, Y.-W. (2006). Tetrahedron Lett. 47, 1059-1063.

organic compounds