(IUCr) Methyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-acetate 1,1-dioxide

Volume 64
Part 5
Page o859
May 2008

Received 19 March 2008
Accepted 11 April 2008
Online 16 April 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.112
Data-to-parameter ratio = 15.9
Details

Methyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-acetate 1,1-dioxide

Waseeq Ahmad Siddiqui,^a ^* Saeed Ahmad,^b Hamid Latif Siddiqui,^c Masood Parvez ^d and Rehana Rashid ^e

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan,^bDepartment of Chemistry, University of Science and Technology, Bannu, Pakistan,^cInstitute of Chemistry, University of the Punjab, Lahore, Pakistan,^dDepartment of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4, and ^eDepartment of Chemistry, University of Balochistan, Quetta, Pakistan
Correspondence e-mail: waseeq_786@yahoo.com

The title molecule, C₁₀H₉NO₅S, is composed of two essentially planar units with a dihedral angle of 89.16 (6)° between them. In the crystal structure, there are weak intermolecular C-HO interactions resulting in dimeric pairs of molecules about inversion centres and chains of molecules extended along the a and c axes, thus stabilizing the structure. In addition, benzothiazole rings lying parallel to each other with centroid-centroid distances of 3.679 (2) and 3.999 (2) Å indicate the existence of [pi] - [pi] stacking interactions.

Related literature

For related literature, see: Kapui et al. (2003); Masashi et al. (1999); Manjarrez et al. (1996); Siddiqui, Ahmad, Khan, Siddiqui & Parvez (2007); Siddiqui, Ahmad, Khan, Siddiqui & Weaver (2007); Siddiqui, Ahmad, Siddiqui et al. (2007); Siddiqui et al. (2008); Xu et al. (2005, 2006).

Experimental

Crystal data

C₁₀H₉NO₅S
M_r = 255.24
Triclinic, $[P \overline 1]$
a = 7.765 (3) Å
b = 8.496 (3) Å
c = 8.776 (4) Å
= 104.39 (2)°
= 100.58 (2)°
= 94.30 (2)°
V = 546.8 (4) Å³
Z = 2
Mo K radiation
= 0.30 mm^-1
T = 173 (2) K
0.16 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997) T_min = 0.953, T_max = 0.976
4654 measured reflections
2468 independent reflections
2040 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.111
S = 1.03
2468 reflections
155 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O5ⁱ	0.95	2.53	3.435 (3)	160
C4-H4O4ⁱⁱ	0.95	2.54	3.209 (3)	128
C8-H8AO2ⁱⁱⁱ	0.99	2.49	3.435 (3)	159
C10-H10CO1^iv	0.98	2.47	3.431 (3)	167
Symmetry codes: (i) x, y, z+1; (ii) -x, -y, -z+2; (iii) -x+1, -y+1, -z+2; (iv) x+1, y, z.

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2607 ).

References

Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.
Fan, H.-F. (1991). SAPI91. Rigaku Corporation, Tokyo, Japan.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Kapui, Z., Varga, M., Urban-Szabo, K., Mikus, E., Szabo, T., Szeredi, J., Finance, O. & Aranyi, P. (2003). J. Pharmacol. Exp. Ther. 305, 1-9.
Manjarrez, N., Pérez, H. I., Solís, A. & Luna, H. (1996). Synth. Commun. 26, 585-591.
Masashi, K., Hideo, T., Kentaro, Y. & Masataka, Y. (1999). Tetrahedron, 55, 14885-14900.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Parvez, M. (2007). Acta Cryst. E63, o4116.
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Weaver, G. W. (2007). Synth. Commun. 37, 767-773.
Siddiqui, W. A., Ahmad, S., Siddiqui, H. L., Tariq, M. I. & Parvez, M. (2007). Acta Cryst. E63, o4001.
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.
Xu, L., Shu, H., Liu, Y., Zhang, S. & Trudell, M. (2006). Tetrahedron, 62, 7902-7910.
Xu, L.-Z., Si, G.-D., Li, Z.-F., Yang, S.-H. & Li, K. (2005). Acta Cryst. E61, o1329-o1330.

organic compounds