4-Methyl-N-[(Z)-3-(4-methyl­phen­ylsulfon­yl)-1,3-thia­zolidin-2-yl­idene]benzene­sulfonamide

Hui-Ling Hu; Geng-Ren Yang; Chun-Wei Yeh

doi:10.1107/S1600536811028807

. 2011 Jul 23;67(Pt 8):o2103. doi: 10.1107/S1600536811028807

4-Methyl-N-[(Z)-3-(4-methylphenylsulfonyl)-1,3-thiazolidin-2-ylidene]benzenesulfonamide

Hui-Ling Hu ^a, Geng-Ren Yang ^a, Chun-Wei Yeh ^b,^*

PMCID: PMC3213545 PMID: 22091122

Abstract

In the crystal structure of the title compound, C₁₇H₁₈N₂O₄S₃, molecules are connected into centrosymmetric dimers via weak intermolecular C—H⋯π interactions. These dimers are further connected through a series of weak C—H⋯O hydrogen bonds, while futher C—H⋯π interactions involving the phenyl and thiazoline rings are also observed. The thiazolidine ring is twisted from the benzene rings rings by dihedral angles of 79.1 (1) and 85.0 (1)°, while the dihedral angle between two benzene rings is 76.0 (1)°.

Related literature

For background to N-heterocyclic sulfanilamide derivatives, see: Kuz’mina et al. (1962 ▶); Jensen & Thorsteinsson (1941 ▶); Hunter & Kolloff (1943 ▶); Hultquist et al. (1951 ▶). For a related synthesis, see: Razvodovskaya et al. (1990 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₄S₃
M _r = 410.51
Monoclinic,
a = 9.3825 (2) Å
b = 14.4047 (2) Å
c = 14.2279 (3) Å
β = 102.666 (1)°
V = 1876.14 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.40 × 0.40 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.845, T _max = 0.845
17749 measured reflections
4652 independent reflections
3756 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.107
S = 1.04
4652 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028807/fj2445sup1.cif

e-67-o2103-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028807/fj2445Isup2.hkl

e-67-o2103-Isup2.hkl^{(227.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028807/fj2445Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C4–C9 and C11–C16 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯Cg1ⁱ	0.97	2.91	3.567 (1)	127
C2—H2B⋯Cg2ⁱⁱ	0.97	3.09	3.821 (1)	134
C1—H1B⋯O1ⁱⁱ	0.97	2.59	3.394 (3)	141
C12—H12A⋯O3ⁱⁱⁱ	0.93	2.47	3.318 (2)	151

Open in a new tab

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

Acknowledgments

We are grateful to the National Science Council of the Republic of China and the Nanya Institute of Technology for support.

supplementary crystallographic information

Comment

In a series of N-heterocyclic sulfanilamide derivatives which prepared and are investigating biologically one of the compounds, 2-sulfanilyl-aminothiazoline, proved to be of particular interest, both chemically and therapeutically. (Kuz'mina et al., 1962; Jensen et al., 1941; Hunter et al., 1943; Hultquist et al., 1951). The synthesis and character the 3-substituted 2-(thiophosphorylimino)thiazolidine compounds are also reported (Razvodovskaya et al., 1990). Within this project the crystal structure of the title compound was determined. The crystal structure features inversion-related dimers linked by the weak intermolecular C—H···pi interactions in the solid state, while Cg1 and Cg2 are the centers of C4—C9 and C11—C16 and these carbon atoms of mean devition from plane are 0.0008 and 0.0043 Å. Weak C—H···O hydrogen bonds among the molecules are also observed in the solid state. The thiazolidine and the phenyl rings are not coplanar but twisted with each other by an interplanar angles of 79.1 (1) and 85.0 (1)°, respectively, while the dihedral angle between two phenyl groups is 76.0 (1)°.

Experimental

The title compound was prepared according to a published procedure (Razvodovskaya et al., 1990). Block like crystals suitable for X-ray crystallography were obtained by slow evaporization of the solvent from a solution of the title compound in methanol.