2-[2-(2-Chloro­phen­yl)-2-oxoeth­yl]-2,3-dihydro-1λ6,2-benzothia­zole-1,1,3-trione

Nazia Sattar; Hamid Latif Siddiqui; Naveed Ahmad; Tanvir Hussain; Masood Parvez

doi:10.1107/S1600536812036653

. 2012 Aug 31;68(Pt 9):o2802. doi: 10.1107/S1600536812036653

2-[2-(2-Chlorophenyl)-2-oxoethyl]-2,3-dihydro-1λ⁶,2-benzothiazole-1,1,3-trione

Nazia Sattar ^a, Hamid Latif Siddiqui ^a, Naveed Ahmad ^a,^*, Tanvir Hussain ^a, Masood Parvez ^b

PMCID: PMC3435829 PMID: 22969675

Abstract

The asymmetric unit of the title compound, C₁₅H₁₀ClNO₄S, contains two independent conformers wherein the 2-chlorophenyl group in one is rotated by approximately 180° compared to the other molecule. This affects the S—N—C—C(=O) and N—C—C(=O)—C torsion angles giving vlaues of −87.0 (2) and 158.7 (2)° in one molecule and −104.3 (2) and −173.4 (2)° in the other. The benzisothiazole ring systems in the two molecules are essentially planar (r.m.s. deviations = 0.017 and 0.010 Å) and form dihedral angles of 73.53 (7) and 73.26 (6)° with the benzene rings. In the crystal, there are weak π–π interactions between the benzene rings of the benzisothiazole groups and symmetry-related chlorobenzene rings with centroid–centroid distances of 3.6178 (13) and 3.6267 (15) Å. In addition, pairs of weak intermolecular C—H⋯O hydrogen bonds form inversion dimers which are connected by further C—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the bromo-substituted analog of the title compound, see: Sattar et al. (2012 ▶). For related structures, see: Maliha et al. (2007 ▶); Siddiqui et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₀ClNO₄S
M _r = 335.75
Triclinic,
a = 7.4933 (2) Å
b = 13.9702 (3) Å
c = 14.5844 (3) Å
α = 109.0462 (14)°
β = 96.5998 (14)°
γ = 93.4671 (11)°
V = 1425.77 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 123 K
0.16 × 0.14 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.934, T _max = 0.958
12676 measured reflections
6602 independent reflections
5465 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.105
S = 1.03
6602 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.46 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: 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036653/lh5517sup1.cif

e-68-o2802-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036653/lh5517Isup2.hkl

e-68-o2802-Isup2.hkl^{(316.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036653/lh5517Isup3.cml

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
C3—H3⋯O7ⁱ	0.95	2.53	3.234 (3)	131
C14—H14⋯O1ⁱⁱ	0.95	2.39	3.284 (3)	158
C17—H17⋯O5ⁱⁱⁱ	0.95	2.43	3.213 (3)	139
C27—H27⋯O7^iv	0.95	2.27	3.133 (3)	151
C30—H30⋯O2^v	0.95	2.51	3.219 (3)	132

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

Acknowledgments

The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

supplementary crystallographic information

Comment

The crystal structure of the bromoisomorph of the title molecule has been reported by our research group recently (Sattar et al., (2012). In this article we report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound contains two conformers (Fig. 1). In both molecules, the benzisothiazol rings S1/N1/C1–C7 and S2/N2/C16–C22 are essentially planar with r.m.s. deviations of fitted atoms being 0.017 and 0.010 Å, respectively, while the mean-planes of the benzene rings C10–C15 and C25–C30 form dihedral angles 73.53 (7) and 73.26 (6)°, respectively, with the mean-planes of the benzisothiazole ring systems. The orientation of the Cl atoms in the two conformers exhibit the most pronounced difference, with opposing orientations in the two molecules. The crystal structure is stabilized by π–π interactions between benzene rings (C1–C6) of the benzisothiazole moities in one molecule and chlorobenzene rings (C25–C30) in a symmetry related molecule centroid to centroid distances of 3.6168 (13) and 3.62672 (15) Å. The crystal packing is further consolidated by weak intermolecular C—H···O hydrogen bonds. The molecule containing S1 forms centrosymmetric dimers via C14—H14···O1ⁱⁱ hydrogen bonding interactions. The other molecule also forms centrosymmetric dimers via C17—H17···O5ⁱⁱⁱ hydrogen bonds. Futher hydrogen bonding interactions of the type C—H···O result in a 3-D network (Fig. 2 and Tab. 1).

The bond distances and angles in both molecules of the title compound agree very well with the corresponding bond distances and angles reported in closely related compounds (Sattar et al., (2012); Maliha et al., 2007; Siddiqui et al., 2007).

Experimental

A mixture of 2-chloro-1-(2-chlorophenyl)ethanone (1.62 g, 8.56 mmol), sodium saccharine (2.1 g, 10.3 mmol) and dimethylformamide (15 mL) was stirred at 383 K for a period of 3 hours under anhydrous conditions. The reaction mixture was cooled to room temperature and transferred to ice cooled water. The pale yellow precipitate of the title compound formed, were filtered and washed with water and cold ethanol, respectively. The crystals suitable for diffraction were grown from a solution of the title compound EtOAc-CHCl₃ (1:1) by slow evaporation. Yield = 2.19 g, 76%; 385–387 K.