N-[4-Acetyl-5-isobutyl-5-(2-p-tolyl­prop­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide ethyl acetate hemisolvate

Loughzail, M.; Mazoir, N.; Maya, C.M.; Berraho, M.; Benharref, A.; Bouhmaida, N.

doi:10.1107/S1600536808039998

Volume 65
Part 1
Page o4
January 2009

Received 28 October 2008
Accepted 27 November 2008
Online 3 December 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.065
wR = 0.143
Data-to-parameter ratio = 24.3
Details

N-[4-Acetyl-5-isobutyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide ethyl acetate hemisolvate

Mohamed Loughzail,^a Noureddine Mazoir,^a Celia M. Maya,^b Moha Berraho,^c Ahmed Benharref ^a and Nouzha Bouhmaida ^d ^*

^aLaboratoire de Chimie des Substances Naturelles, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco,^bInstituto de Química Física Rocasolano, Consejo Superior de Investigaciones Científicas, Serrano 119, 28002 Madrid, Spain,^cLaboratoire de Chimie de Coordination, Unité Matériaux, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^dLaboratoire des Sciences des Matériaux, Département de Physique, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
Correspondence e-mail: nouzha@ucam.ac.ma

The racemic title compound, a new terpenoid, C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂, was synthesized from Cedrus Atlantica essential oil. The compound crystallizes with a disordered ethyl acetate solvent molecule. The thiadiazole ring is almost planar, with a maximum deviation from the mean plane of 0.015 (2) Å for the C atom connected to the isobutyl group and has a puckering amplitude of 0.026 (2) Å. The dihedral angle between the benzene and thiadiazole rings is 18.32 (8)°. The crystal packing involves intermolecular N-HO hydrogen bonds.

Related literature

For 1,3,4-thiadiazole derivatives and their biological activity, see: Abdou et al. (1991); Sakthivel et al. (2008); Tehranchian et al. (2005); Wang et al. (1999, 2004). For preparative methods, see: Beatriz et al., 2002; Mohammed et al. (2008); For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₀H₂₉N₃O₂S·0.5C₄H₈O₂
M_r = 419.57
Monoclinic, P 2₁ /n
a = 7.8713 (3) Å
b = 12.7587 (5) Å
c = 22.9688 (9) Å
= 90.937 (2)°
V = 2306.39 (16) Å³
Z = 4
Mo K radiation
= 0.17 mm^-1
T = 295 K
0.5 × 0.4 × 0.3 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer
Absorption correction: none
27541 measured reflections
7243 independent reflections
6688 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.143
S = 1.23
7243 reflections
298 parameters
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.86	1.95	2.812 (2)	179
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2168 ).

Acknowledgements

We thank Professor Jean-Claude Daran, Laboratoire de Chimie de Coordination, Toulouse, France, for his fruitful help.

References

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Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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Mohammed, T., Mazoir, N., Daran, J.-C., Berraho, M. & Benharref, A. (2008). Acta Cryst. E64, o610-o611.
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organic compounds