Dimethyl 3-acetyl-3-(1,3-benzothia­zol-2-yl)penta­nedioate

Baryala, Y.; Salem, M.; Essassi, E.M.; Reuter, H.; Izaaryene, M.

doi:10.1107/S1600536808035782

Volume 64
Part 12
Page o2290
December 2008

Received 19 September 2008
Accepted 31 October 2008
Online 8 November 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.083
Data-to-parameter ratio = 17.8
Details

Dimethyl 3-acetyl-3-(1,3-benzothiazol-2-yl)pentanedioate

Yamna Baryala,^a Moussa Salem,^a El Mokhtar Essassi,^b Hans Reuter ^c ^* and Maher Izaaryene ^c

^aLaboratoire de Chimie Organique et Études Physicochimiques, ENS Rabat, Morocco,^bLaboratoire de Chimie Organique Hétérocyclique, Université Mohammed V Rabat, Morocco, and ^cInstitute of Chemistry, University of Osnabrück, Barbarastrasse 7, D-49069 Osnabrück, Germany
Correspondence e-mail: hreuter@uos.de

The title compound, C₁₆H₁₇NO₅S, was one of two condensation products from the reaction of 1-(1,3-benzothiazol-2-yl)propan-2-one with methyl chloroacetate. The non-H atoms in each of the four substituent groups on the central quaternary C atom are virtually coplanar. The maximum deviations from the least-squares planes are 0.015 (2) and 0.020 (2) Å for the methyl C atoms in the methyl acetate substituents and 0.033 (1) Å for the linked C atom of the benzothiazole substituent. The S, C and N atoms in the thiazole ring of the benzothiazole substituent lie -0.037 (2), 0.046 (2) and -0.028 (2) Å, respectively, from the mean plane defined by the benzene ring atoms.

Related literature

For general background, see: Palmer et al. (1971); Bénéteau et al., 1999; El-Sherbeny (2000); Abayeh et al. (1994); Ivanov & Yuritsyn (1971); Monsanto (1968); Lee et al. (2001). For related structures, see: Chen (1994); Chu et al. (2003).

Experimental

Crystal data

C₁₆H₁₇NO₅S
M_r = 335.37
Monoclinic, P 2₁ /c
a = 14.4075 (3) Å
b = 8.8089 (2) Å
c = 13.8968 (3) Å
= 118.011 (1)°
V = 1557.10 (6) Å³
Z = 4
Mo K radiation
= 0.23 mm^-1
T = 100 (2) K
0.54 × 0.47 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.883, T_max = 0.945
94263 measured reflections
3766 independent reflections
3396 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.083
S = 1.02
3766 reflections
211 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.23 e Å^-3

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2155 ).

References

Abayeh, O. J., Olagbemiro, T. O., Agho, M. O. & Amupitan, J. O. (1994). Bull. Soc. Chim. Belg. 103, 687-690.
Bénéteau, V., Besson, T., Guillard, J., Léonce, S. & Pfeiffer, B. J. (1999). Eur. J. Med. Chem. 34, 1053-1060.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, W. (1994). J. Organomet. Chem. 471, 69-70.
Chu, Q., Wang, Z., Huang, Q., Yan, C. & Zhu, S. (2003). New J. Chem. 27, 1522-1527.
El-Sherbeny, M. A. (2000). Arzneim. Forsch. 50, 848-853.
Ivanov, S. V. & Yuritsyn, V. S. (1971). Neftekhimiya, 11, 99-107.
Lee, C. L., Lam, Y. & Lee, S.-Y. (2001). Tetrahedron Lett. 42, 109-111.
Monsanto, C. O. (1968). Br. Patent No. 1 106 577.
Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds