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

Waseeq Ahmad Siddiqui; Saeed Ahmad; Hamid Latif Siddiqui; Masood Parvez; Rehana Rashid

doi:10.1107/S1600536808009951

. 2008 Apr 16;64(Pt 5):o859. doi: 10.1107/S1600536808009951

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, Rehana Rashid ^e

PMCID: PMC2961185 PMID: 21202346

Abstract

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—H⋯O 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 π–π 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,
a = 7.765 (3) Å
b = 8.496 (3) Å
c = 8.776 (4) Å
α = 104.39 (2)°
β = 100.58 (2)°
γ = 94.30 (2)°
V = 546.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.111
S = 1.03
2468 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009951/lh2607sup1.cif

e-64-0o859-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009951/lh2607Isup2.hkl

e-64-0o859-Isup2.hkl^{(118.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5ⁱ	0.95	2.53	3.435 (3)	160
C4—H4⋯O4ⁱⁱ	0.95	2.54	3.209 (3)	128
C8—H8A⋯O2ⁱⁱⁱ	0.99	2.49	3.435 (3)	159
C10—H10C⋯O1^iv	0.98	2.47	3.431 (3)	167

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

Comment

Saccharin derivatives are considered to be the most potent orally active human leucocyte elastase (HLE) inhibitors for the treatment of chronic obstructive pulmonary disease (COPD), acute respiratory distress syndrome (ARDS), cystic fibrosis, asthma and other inflammatory diseases (Kapui et al., 2003). Various biologically important saccharin skeletons and their N-alkyl derivatives were efficiently prepared (Xu et al., 2006) by chromium oxide-catalyzed oxidation of N-alkyl(o-methyl)arenesulfonamides in acetonitrile besides the already developed methodology utilizing irradiation techniques for similar type of conversions (Masashi et al., 1999). In continuation to our research on benzene, 1,2-benzothiazine 1,1-dioxide and saccharin derivatives (Siddiqui et al., 2008; Siddiqui, Ahmad, Khan, Siddiqui & Weaver, 2007), we report herein the crystal structure of the title compound, (I).

The structure of (I) is composed of an essentially planar moiety, S1/N1/O1/C1—C7 with maximum deviations from the least-square planes being: O1 = -0.0540 (12) and N1 = 0.0540 (13) Å, and an approximately planar moiety C8—C10/O4/O5 with maximum deviation of 0.0766 (13) Å for C8. The two moieties are oriented with a dihedral angle of 89.16 (6)° between their least-squares planes. The structure is stabilized by four rather weak intermolecular interactions of the type C—H···O (Fig. 2 and Table 1). Of these interactions, C4—H4···O5 and C8—H8A···O2 H-bonds result in dimeric pairs of (I) while C10—H10···O1 and C2—H2···O5 result in chains of molecules extended along the a- and c-axes, respectively. The benzothiazole rings in (I) lie parallel to each other about the origin with the shortest distance between the centroids of the benzene rings of the adjacent molecules is 3.679 (2) Å which indicates the existence of π-π stacking interactions. The thiazoline rings located about inversion centers in the middle of the b axis (at 0, 1/2, 0) also show π-π interaction with centroids of these rings separated by 3.999 (2) Å (Fig. 3). The molecular dimensions in (I) are in agreement with the corresponding dimensions reported in similar structures (Xu et al., 2005; Siddiqui, Ahmad, Khan, Siddiqui & Parvez, 2007; Siddiqui, Ahmad, Siddiqui et al., 2007; Siddiqui et al., 2008).

Experimental

The compound (I) was prepared following the prcedures reported earlier (Manjarrez et al., 1996). Crystals suitable for X-ray crystallography were grown from a solution of CH₃OH by slow evaporation at 313 K.