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

Hu, H.-L.; Yang, G.-R.; Yeh, C.-W.

doi:10.1107/S1600536811028807

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2103

doi:10.1107/S1600536811028807

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

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

^aDepartment of Chemical Engineering and Material Engineering, Graduate School of Materials Applied Technology, Nanya Institute of Technology, Chung-Li, Taiwan, and ^bDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li, Taiwan
^*Correspondence e-mail: cwyeh@cycu.org.tw

(Received 9 July 2011; accepted 17 July 2011; online 23 July 2011)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.037
wR(F²) = 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

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
Symmetry codes: (i) -x, -y, -z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811028807/fj2445sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811028807/fj2445Isup3.cml

checkCIF report

Comment top

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)°.

Related literature top

For a 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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Crystal structure of the title compound with atom labeling and displacement ellipsoids drawn at the 30% probability level.

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

Crystal data top

C₁₇H₁₈N₂O₄S₃	F(000) = 856
M_r = 410.51	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8638 reflections
a = 9.3825 (2) Å	θ = 2.4–28.2°
b = 14.4047 (2) Å	µ = 0.42 mm⁻¹
c = 14.2279 (3) Å	T = 296 K
β = 102.666 (1)°	Block, colourless
V = 1876.14 (6) Å³	0.40 × 0.40 × 0.40 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4652 independent reflections
Radiation source: fine-focus sealed tube	3756 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.845, T_max = 0.845	k = −15→19
17749 measured reflections	l = −17→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0497P)² + 0.6237P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4652 reflections	Δρ_max = 0.29 e Å⁻³
236 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (9)

Crystal data top

C₁₇H₁₈N₂O₄S₃	V = 1876.14 (6) Å³
M_r = 410.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3825 (2) Å	µ = 0.42 mm⁻¹
b = 14.4047 (2) Å	T = 296 K
c = 14.2279 (3) Å	0.40 × 0.40 × 0.40 mm
β = 102.666 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4652 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3756 reflections with I > 2σ(I)
T_min = 0.845, T_max = 0.845	R_int = 0.025
17749 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
4652 reflections	Δρ_min = −0.29 e Å⁻³
236 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.16502 (15)	0.17067 (10)	0.38640 (10)	0.0446 (3)
N2	0.08736 (15)	0.26664 (10)	0.25505 (10)	0.0448 (3)
S1	0.34585 (5)	0.17353 (4)	0.27357 (4)	0.06158 (16)
S2	0.10549 (5)	0.31474 (3)	0.15432 (3)	0.04983 (13)
S3	0.01808 (5)	0.19186 (3)	0.43270 (3)	0.04805 (13)
O1	−0.00727 (19)	0.38361 (9)	0.13422 (10)	0.0693 (4)
O2	0.25206 (18)	0.34381 (12)	0.15775 (11)	0.0739 (4)
O3	0.04496 (18)	0.13807 (11)	0.51854 (10)	0.0702 (4)
O4	0.00217 (15)	0.28956 (9)	0.43817 (10)	0.0580 (3)
C1	0.2585 (2)	0.08847 (14)	0.41762 (15)	0.0590 (5)
H1A	0.2091	0.0321	0.3909	0.071*
H1B	0.2818	0.0836	0.4873	0.071*
C2	0.3947 (2)	0.10280 (16)	0.38077 (16)	0.0664 (6)
H2A	0.4335	0.0436	0.3656	0.080*
H2B	0.4684	0.1338	0.4290	0.080*
C3	0.18420 (17)	0.21042 (11)	0.30207 (11)	0.0407 (3)
C4	0.06041 (19)	0.22754 (11)	0.06650 (12)	0.0431 (4)
C5	−0.08309 (19)	0.19554 (12)	0.04084 (13)	0.0481 (4)
H5A	−0.1533	0.2177	0.0723	0.058*
C6	−0.1198 (2)	0.13072 (13)	−0.03153 (14)	0.0534 (4)
H6A	−0.2156	0.1094	−0.0486	0.064*
C7	−0.0173 (2)	0.09647 (13)	−0.07954 (13)	0.0542 (4)
C8	0.1244 (2)	0.12907 (15)	−0.05287 (14)	0.0607 (5)
H8A	0.1943	0.1068	−0.0844	0.073*
C9	0.1647 (2)	0.19422 (14)	0.01986 (14)	0.0538 (4)
H9A	0.2606	0.2152	0.0370	0.065*
C10	−0.0606 (3)	0.02670 (16)	−0.15964 (16)	0.0787 (7)
H10A	−0.1623	0.0119	−0.1675	0.118*
H10B	−0.0034	−0.0287	−0.1439	0.118*
H10C	−0.0438	0.0524	−0.2185	0.118*
C11	−0.12963 (18)	0.14496 (12)	0.34887 (12)	0.0460 (4)
C12	−0.1544 (2)	0.04982 (13)	0.35063 (15)	0.0578 (5)
H12A	−0.0965	0.0124	0.3971	0.069*
C13	−0.2660 (2)	0.01228 (15)	0.28240 (17)	0.0652 (5)
H13A	−0.2837	−0.0512	0.2836	0.078*
C14	−0.3526 (2)	0.06605 (15)	0.21206 (15)	0.0579 (5)
C15	−0.3267 (2)	0.16119 (15)	0.21243 (15)	0.0557 (5)
H15A	−0.3850	0.1986	0.1661	0.067*
C16	−0.21635 (19)	0.20075 (13)	0.28026 (14)	0.0507 (4)
H16A	−0.2002	0.2644	0.2800	0.061*
C17	−0.4719 (3)	0.0231 (2)	0.13607 (19)	0.0864 (8)
H17A	−0.4738	−0.0427	0.1461	0.130*
H17B	−0.4536	0.0354	0.0735	0.130*
H17C	−0.5644	0.0494	0.1403	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0461 (7)	0.0435 (7)	0.0418 (7)	0.0049 (6)	0.0045 (6)	−0.0002 (6)
N2	0.0453 (7)	0.0459 (8)	0.0429 (7)	0.0017 (6)	0.0095 (6)	0.0013 (6)
S1	0.0508 (3)	0.0734 (3)	0.0623 (3)	0.0140 (2)	0.0163 (2)	−0.0073 (2)
S2	0.0627 (3)	0.0401 (2)	0.0470 (2)	−0.00536 (18)	0.0128 (2)	0.00129 (17)
S3	0.0555 (3)	0.0491 (3)	0.0406 (2)	−0.00057 (18)	0.01281 (18)	−0.00071 (17)
O1	0.1039 (12)	0.0425 (7)	0.0589 (8)	0.0189 (7)	0.0122 (8)	0.0043 (6)
O2	0.0802 (10)	0.0758 (10)	0.0684 (9)	−0.0367 (8)	0.0217 (8)	−0.0044 (8)
O3	0.0878 (11)	0.0805 (10)	0.0427 (7)	0.0010 (8)	0.0149 (7)	0.0108 (7)
O4	0.0645 (8)	0.0504 (7)	0.0619 (8)	0.0006 (6)	0.0197 (7)	−0.0130 (6)
C1	0.0684 (12)	0.0496 (10)	0.0521 (10)	0.0146 (9)	−0.0017 (9)	0.0011 (8)
C2	0.0637 (12)	0.0655 (13)	0.0631 (12)	0.0251 (10)	−0.0009 (10)	−0.0143 (10)
C3	0.0399 (8)	0.0402 (8)	0.0402 (8)	−0.0027 (6)	0.0052 (6)	−0.0082 (6)
C4	0.0484 (9)	0.0396 (8)	0.0416 (8)	0.0018 (7)	0.0110 (7)	0.0055 (7)
C5	0.0472 (9)	0.0468 (9)	0.0520 (10)	0.0050 (7)	0.0144 (7)	0.0031 (8)
C6	0.0529 (10)	0.0479 (10)	0.0546 (10)	−0.0025 (8)	0.0014 (8)	0.0027 (8)
C7	0.0726 (12)	0.0458 (10)	0.0403 (9)	0.0106 (9)	0.0041 (8)	0.0038 (7)
C8	0.0659 (12)	0.0680 (13)	0.0519 (11)	0.0153 (10)	0.0210 (9)	−0.0008 (9)
C9	0.0484 (9)	0.0636 (11)	0.0512 (10)	0.0007 (8)	0.0153 (8)	0.0020 (8)
C10	0.1124 (19)	0.0631 (13)	0.0513 (12)	0.0143 (13)	−0.0025 (12)	−0.0083 (10)
C11	0.0473 (9)	0.0452 (9)	0.0478 (9)	−0.0052 (7)	0.0155 (7)	0.0038 (7)
C12	0.0651 (12)	0.0470 (10)	0.0626 (12)	−0.0066 (9)	0.0171 (9)	0.0100 (9)
C13	0.0710 (13)	0.0470 (11)	0.0826 (15)	−0.0152 (9)	0.0279 (11)	−0.0052 (10)
C14	0.0491 (10)	0.0687 (12)	0.0607 (11)	−0.0102 (9)	0.0226 (9)	−0.0147 (10)
C15	0.0441 (9)	0.0665 (12)	0.0578 (11)	−0.0001 (8)	0.0139 (8)	0.0053 (9)
C16	0.0467 (9)	0.0451 (9)	0.0622 (11)	−0.0022 (7)	0.0157 (8)	0.0064 (8)
C17	0.0689 (14)	0.0996 (19)	0.0894 (18)	−0.0144 (13)	0.0148 (13)	−0.0413 (15)

Geometric parameters (Å, º) top

N1—C3	1.376 (2)	C6—H6A	0.9300
N1—C1	1.483 (2)	C7—C8	1.382 (3)
N1—S3	1.6811 (15)	C7—C10	1.507 (3)
N2—C3	1.289 (2)	C8—C9	1.387 (3)
N2—S2	1.6340 (15)	C8—H8A	0.9300
S1—C3	1.7368 (16)	C9—H9A	0.9300
S1—C2	1.808 (2)	C10—H10A	0.9600
S2—O2	1.4282 (15)	C10—H10B	0.9600
S2—O1	1.4327 (15)	C10—H10C	0.9600
S2—C4	1.7566 (17)	C11—C16	1.383 (3)
S3—O4	1.4192 (14)	C11—C12	1.391 (3)
S3—O3	1.4215 (14)	C12—C13	1.373 (3)
S3—C11	1.7536 (18)	C12—H12A	0.9300
C1—C2	1.498 (3)	C13—C14	1.380 (3)
C1—H1A	0.9700	C13—H13A	0.9300
C1—H1B	0.9700	C14—C15	1.392 (3)
C2—H2A	0.9700	C14—C17	1.508 (3)
C2—H2B	0.9700	C15—C16	1.375 (3)
C4—C9	1.383 (2)	C15—H15A	0.9300
C4—C5	1.394 (2)	C16—H16A	0.9300
C5—C6	1.377 (3)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17B	0.9600
C6—C7	1.386 (3)	C17—H17C	0.9600

C3—N1—C1	114.30 (15)	C7—C6—H6A	119.2
C3—N1—S3	122.77 (11)	C8—C7—C6	118.23 (17)
C1—N1—S3	120.66 (13)	C8—C7—C10	121.2 (2)
C3—N2—S2	121.62 (12)	C6—C7—C10	120.6 (2)
C3—S1—C2	92.76 (9)	C7—C8—C9	121.55 (18)
O2—S2—O1	117.85 (10)	C7—C8—H8A	119.2
O2—S2—N2	112.27 (9)	C9—C8—H8A	119.2
O1—S2—N2	104.73 (8)	C4—C9—C8	119.15 (18)
O2—S2—C4	108.29 (9)	C4—C9—H9A	120.4
O1—S2—C4	107.52 (9)	C8—C9—H9A	120.4
N2—S2—C4	105.40 (8)	C7—C10—H10A	109.5
O4—S3—O3	119.63 (9)	C7—C10—H10B	109.5
O4—S3—N1	107.86 (8)	H10A—C10—H10B	109.5
O3—S3—N1	103.39 (8)	C7—C10—H10C	109.5
O4—S3—C11	110.02 (9)	H10A—C10—H10C	109.5
O3—S3—C11	109.83 (9)	H10B—C10—H10C	109.5
N1—S3—C11	104.90 (8)	C16—C11—C12	120.69 (18)
N1—C1—C2	106.21 (17)	C16—C11—S3	120.74 (14)
N1—C1—H1A	110.5	C12—C11—S3	118.52 (15)
C2—C1—H1A	110.5	C13—C12—C11	118.67 (19)
N1—C1—H1B	110.5	C13—C12—H12A	120.7
C2—C1—H1B	110.5	C11—C12—H12A	120.7
H1A—C1—H1B	108.7	C12—C13—C14	121.87 (19)
C1—C2—S1	107.17 (13)	C12—C13—H13A	119.1
C1—C2—H2A	110.3	C14—C13—H13A	119.1
S1—C2—H2A	110.3	C13—C14—C15	118.41 (19)
C1—C2—H2B	110.3	C13—C14—C17	121.1 (2)
S1—C2—H2B	110.3	C15—C14—C17	120.5 (2)
H2A—C2—H2B	108.5	C16—C15—C14	120.96 (19)
N2—C3—N1	120.10 (15)	C16—C15—H15A	119.5
N2—C3—S1	128.55 (13)	C14—C15—H15A	119.5
N1—C3—S1	111.35 (12)	C15—C16—C11	119.39 (17)
C9—C4—C5	120.25 (17)	C15—C16—H16A	120.3
C9—C4—S2	120.28 (14)	C11—C16—H16A	120.3
C5—C4—S2	119.40 (13)	C14—C17—H17A	109.5
C6—C5—C4	119.28 (17)	C14—C17—H17B	109.5
C6—C5—H5A	120.4	H17A—C17—H17B	109.5
C4—C5—H5A	120.4	C14—C17—H17C	109.5
C5—C6—C7	121.53 (18)	H17A—C17—H17C	109.5
C5—C6—H6A	119.2	H17B—C17—H17C	109.5

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y, −z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄S₃
M_r	410.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.3825 (2), 14.4047 (2), 14.2279 (3)
β (°)	102.666 (1)
V (Å³)	1876.14 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.40 × 0.40 × 0.40

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.845, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	17749, 4652, 3756
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.04
No. of reflections	4652
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y, −z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x, −y, −z+1.

Acknowledgements

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

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hultquist, M. E., Germann, R. P., Webb, J. S., Wright, W. B. Jr, Roth, B., Smith, J. M. Jr & SubbaRow, Y. (1951). J. Am. Chem. Soc. 73, 2558–2566. CrossRef CAS Web of Science Google Scholar
Hunter, J. H. & Kolloff, H. G. (1943). J. Am. Chem. Soc. 65, 156–159. CrossRef CAS Google Scholar
Jensen, K. A. & Thorsteinsson, T. (1941). Dansk Tidsskrift Farmaci, 15, 41–77. CAS Google Scholar
Kuz'mina, K. K., Ostroumova, N. G., Markova, Yu. V. & Shchukina, M. N. (1962). Zhurnal Obshchei Khimii. 32, 3390–3393. CAS Google Scholar
Razvodovskaya, L. V., Vorob'eva, N. N., Grapov, A. F. & Mel'nikov, N. N. (1990). Zhurnal Obshchei Khimii, 60, 1518–1525. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o2103

doi:10.1107/S1600536811028807

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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