1-Benzyl-3-methyl-3′,5′-diphenyl­spiro­[quinoxaline-2(1H),2′(3′H)-1,3,4-thia­diazole]

Anothane, C.A.; Bouhfid, R.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811052731

Volume 68
Part 1
Page o103
January 2012

Received 7 December 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.045
wR = 0.135
Data-to-parameter ratio = 24.5
Details

1-Benzyl-3-methyl-3',5'-diphenylspiro[quinoxaline-2(1H),2'(3'H)-1,3,4-thiadiazole]

Caleb Ahoya Anothane,^a Rachid Bouhfid,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco,^bInstitute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l'Armée Royale, Rabat, Morocco,^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

In the title spiro compound, C₂₉H₂₄N₄S, the quinoxaline and thiadiazole ring systems share a common C atom; their mean planes are aligned at 87.0 (1)° in one molecule and at 84.1 (1)° in the other independent molecule. The thiazole ring possesses two aromatic ring substituents and is roughly coplanar with these rings [the dihedral angles between the thiadiazole and phenyl rings are 10.7 (1) and 11.7 (1)° in one molecule, and 16.8 (1) and 17.7 (1)° in the other]. The aromatic ring of the benzyl unit of one molecule is disordered over two orientations in a 1:1 ratio.

Related literature

For the structure of a related molecule, see: Anothane et al. (2010).

Experimental

Crystal data

C₂₉H₂₄N₄S
M_r = 460.58
Triclinic, $[P \overline 1]$
a = 13.5441 (2) Å
b = 14.8971 (2) Å
c = 15.0149 (2) Å
= 66.431 (1)°
= 63.921 (1)°
= 65.275 (1)°
V = 2383.45 (6) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 293 K
0.35 × 0.34 × 0.17 mm

Data collection

Bruker APEX DUO diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.946, T_max = 0.973
69257 measured reflections
14918 independent reflections
10508 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.135
S = 1.01
14918 reflections
609 parameters
37 restraints
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.22 e Å^-3

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5152 ).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Anothane, C. A., Bouhfid, R., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o3227.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds