(5S)-5-Methyl-3-phenyl-2-sulfanyl­idene-1,3-thia­zolidin-4-one

Jiang, J.-R.; Xu, F.; Ke, Z.-L.; Li, L.

doi:10.1107/S1600536811051312

organic compounds

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Volume 68| Part 1| January 2012| Page o34

doi:10.1107/S1600536811051312

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(5S)-5-Methyl-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one

Jun-Rong Jiang,^a ^* Feng Xu,^a Zhong-Lu Ke ^a and Li Li ^a

^aDepartment of Biological & Chemical Engineering, Taizhou Vocational & Technical College, Taizhou 318000, People's Republic of China
^*Correspondence e-mail: jiangjr@tzvtc.com

(Received 15 November 2011; accepted 29 November 2011; online 7 December 2011)

In the title molecule, C₁₀H₉NOS₂, the 2-sulfanylidenethiazolidin-4-one mean plane and phenyl ring form a dihedral angle of 81.7 (1)°. In the crystal, C—H⋯π interactions link molecules into helical chains in [010].

Related literature

For related structures, see: Gattow et al. (1983 ); Rang et al. (1997 ). For applications of 2-sulfanylidenethiazolidin-4-one derivatives, see: Zidar et al. (2010 ); Powers et al. (2006 ).

Experimental

Crystal data

C₁₀H₉NOS₂
M_r = 223.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.8527 (4) Å
b = 8.6643 (5) Å
c = 17.5572 (15) Å
V = 1042.44 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 153 K
0.30 × 0.20 × 0.18 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008 ) T_min = 0.872, T_max = 0.919
9028 measured reflections
2777 independent reflections
2561 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.064
S = 1.00
2777 reflections
128 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1155 Friedel pairs
Flack parameter: −0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cgⁱ	1.00	2.47	3.4321 (16)	162
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear; data reduction: CrystalClear ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051312/cv5203sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051312/cv5203Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051312/cv5203Isup3.cml

checkCIF report

Comment top

2-sulfanylidenethiazolidin-4-one derivatives are known as compounds with potential antifungal activities (Zidar et al., 2010) and potential drugs-inhibitors of the HCV-RNA polymerase (Powers et al., 2006). Herewith we present the title compound (I), which is a new 2-sulfanylidenethiazolidin-4-one derivative.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds 3-(S)-(1-phenylethyl)-5-methyl-2-sulfanylidenethiazolidin-4-one (Rang et al., 1997) and 5-methyl-2-sulfanylidenethiazolidin-4-one (Gattow et al., 1983). The 2-sulfanylidenethiazolidin-4-one and phenyl rings form a dihedral angle of 81.7 (1)°. In the crystal structure, intermolecular C—H···π interactions (Table 1) link molecules into helical chains in [010].

Related literature top

For related structures, see: Gattow et al. (1983); Rang et al. (1997). For applications of 2-sulfanylidenethiazolidin-4-one derivatives, see: Zidar et al. (2010); Powers et al. (2006).

Experimental top

To 54 ml of concentrated ammonia in an ice-salt bath was added 13.95 g(0.15 mol) of benzylamine. carbon bisulfide 19.5 ml(24.6 g,0.323 mol) was added dropwise over a period 2 h and stirring continued for 4 h.The dithiocarbamate precipitated was allowed to stand overnight. It was filtered(warning:filtered to be immediately used), washed with cold ether and dried by suction. The sodium 2-bromopropionate solution was prepared by 15.3 g(0.1 mol) of 2-bromopropionic acid in 9 ml of water and 3.5 g(0.0875 mol)of sodium hydroxide in 6 ml of water,and adding saturated NaHCO₃ solution until the solution was basic.The sodium 2-bromopropionate solution was stirred, cooled to 273 K and the dithiocarbamate added by batch about 10 min.After the mixture was stirred for 1 h at the same condition,it was allowed to warm up to r.t. and stand 30 min.Then a hot solution of concentrated HCl plus water(40 ml+27 ml)was added to it.The mixture was boiled for 10 min and cooled to r.t.The precipitate was filtered, washed with cold water and little cold ethanol.The crude product was recrystallized from ethanol to yield 13.6 g(61%) yellow needle-like compounds.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids.

(5S)-5-Methyl-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one top

Crystal data top

C₁₀H₉NOS₂	F(000) = 464
M_r = 223.30	D_x = 1.423 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3919 reflections
a = 6.8527 (4) Å	θ = 2.3–29.1°
b = 8.6643 (5) Å	µ = 0.48 mm⁻¹
c = 17.5572 (15) Å	T = 153 K
V = 1042.44 (12) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.18 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2777 independent reflections
Radiation source: fine-focus sealed tube	2561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 28.5714 pixels mm^-1	θ_max = 29.1°, θ_min = 2.6°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −11→10
T_min = 0.872, T_max = 0.919	l = −23→22
9028 measured reflections

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0326P)² + 0.086P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.014
2777 reflections	Δρ_max = 0.30 e Å⁻³
128 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1155 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (6)

Crystal data top

C₁₀H₉NOS₂	V = 1042.44 (12) Å³
M_r = 223.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.8527 (4) Å	µ = 0.48 mm⁻¹
b = 8.6643 (5) Å	T = 153 K
c = 17.5572 (15) Å	0.30 × 0.20 × 0.18 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2777 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	2561 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.919	R_int = 0.029
9028 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.064	Δρ_max = 0.30 e Å⁻³
S = 1.00	Δρ_min = −0.17 e Å⁻³
2777 reflections	Absolute structure: Flack (1983), 1155 Friedel pairs
128 parameters	Absolute structure parameter: −0.01 (6)
1 restraint

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
S1	0.11471 (5)	0.55991 (4)	0.42516 (2)	0.02375 (9)
S2	0.13997 (6)	0.70725 (4)	0.57733 (2)	0.02665 (10)
O1	0.53389 (18)	0.27885 (14)	0.46834 (6)	0.0334 (3)
N3	0.36082 (17)	0.47158 (13)	0.52694 (6)	0.0177 (2)
C2	0.2145 (2)	0.57762 (16)	0.51556 (8)	0.0186 (3)
C4	0.4056 (2)	0.37374 (17)	0.46629 (8)	0.0212 (3)
C5	0.2751 (2)	0.40173 (16)	0.39840 (8)	0.0204 (3)
H5	0.1937	0.3075	0.3899	0.025*
C6	0.3913 (2)	0.4338 (2)	0.32607 (8)	0.0285 (3)
H6A	0.4889	0.3525	0.3188	0.034*
H6B	0.4569	0.5339	0.3306	0.034*
H6C	0.3027	0.4357	0.2823	0.034*
C7	0.4603 (2)	0.45370 (16)	0.59871 (7)	0.0184 (3)
C8	0.3715 (2)	0.36714 (18)	0.65529 (8)	0.0246 (3)
H8	0.2451	0.3249	0.6476	0.030*
C9	0.4698 (3)	0.34305 (19)	0.72335 (9)	0.0285 (4)
H9	0.4112	0.2829	0.7624	0.034*
C10	0.6522 (2)	0.40624 (18)	0.73445 (8)	0.0280 (3)
H10	0.7178	0.3909	0.7815	0.034*
C11	0.7409 (2)	0.4923 (2)	0.67723 (9)	0.0274 (3)
H11	0.8671	0.5348	0.6852	0.033*
C12	0.6448 (2)	0.51620 (16)	0.60833 (8)	0.0226 (3)
H12	0.7045	0.5742	0.5687	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02356 (17)	0.02662 (18)	0.02108 (17)	0.00623 (15)	−0.00460 (16)	−0.00175 (15)
S2	0.02865 (19)	0.02565 (18)	0.02565 (19)	0.00662 (16)	0.00106 (18)	−0.00678 (16)
O1	0.0377 (7)	0.0365 (7)	0.0259 (6)	0.0192 (6)	−0.0044 (5)	−0.0058 (5)
N3	0.0179 (5)	0.0197 (5)	0.0155 (5)	0.0002 (5)	−0.0008 (5)	−0.0004 (4)
C2	0.0180 (6)	0.0183 (6)	0.0194 (6)	−0.0016 (5)	0.0012 (5)	0.0008 (5)
C4	0.0225 (8)	0.0226 (7)	0.0186 (7)	0.0013 (6)	0.0004 (6)	−0.0003 (6)
C5	0.0230 (7)	0.0198 (7)	0.0186 (6)	0.0002 (6)	−0.0007 (6)	−0.0027 (6)
C6	0.0301 (8)	0.0347 (8)	0.0208 (7)	0.0031 (8)	0.0021 (6)	0.0006 (7)
C7	0.0216 (6)	0.0182 (7)	0.0154 (6)	0.0014 (5)	−0.0005 (5)	−0.0012 (5)
C8	0.0227 (7)	0.0286 (7)	0.0227 (7)	−0.0028 (7)	0.0021 (6)	−0.0003 (6)
C9	0.0374 (9)	0.0291 (8)	0.0189 (7)	−0.0009 (7)	0.0043 (7)	0.0031 (6)
C10	0.0355 (9)	0.0292 (8)	0.0193 (7)	0.0057 (7)	−0.0065 (7)	−0.0017 (6)
C11	0.0254 (7)	0.0281 (8)	0.0286 (8)	−0.0028 (6)	−0.0078 (6)	−0.0007 (6)
C12	0.0243 (7)	0.0205 (6)	0.0231 (7)	−0.0025 (6)	−0.0008 (6)	0.0023 (6)

Geometric parameters (Å, º) top

S1—C2	1.7350 (14)	C6—H6C	0.9800
S1—C5	1.8184 (15)	C7—C12	1.3856 (19)
S2—C2	1.6427 (14)	C7—C8	1.386 (2)
O1—C4	1.2043 (17)	C8—C9	1.387 (2)
N3—C2	1.3746 (17)	C8—H8	0.9500
N3—C4	1.3951 (18)	C9—C10	1.379 (2)
N3—C7	1.4412 (17)	C9—H9	0.9500
C4—C5	1.510 (2)	C10—C11	1.391 (2)
C5—C6	1.5245 (19)	C10—H10	0.9500
C5—H5	1.0000	C11—C12	1.393 (2)
C6—H6A	0.9800	C11—H11	0.9500
C6—H6B	0.9800	C12—H12	0.9500

C2—S1—C5	93.72 (7)	H6A—C6—H6C	109.5
C2—N3—C4	117.10 (11)	H6B—C6—H6C	109.5
C2—N3—C7	122.96 (11)	C12—C7—C8	121.67 (13)
C4—N3—C7	119.87 (12)	C12—C7—N3	119.76 (12)
N3—C2—S2	126.00 (10)	C8—C7—N3	118.49 (13)
N3—C2—S1	111.18 (10)	C7—C8—C9	119.05 (15)
S2—C2—S1	122.82 (9)	C7—C8—H8	120.5
O1—C4—N3	123.54 (13)	C9—C8—H8	120.5
O1—C4—C5	124.46 (13)	C10—C9—C8	120.14 (15)
N3—C4—C5	112.01 (12)	C10—C9—H9	119.9
C4—C5—C6	112.18 (12)	C8—C9—H9	119.9
C4—C5—S1	105.97 (10)	C9—C10—C11	120.47 (14)
C6—C5—S1	113.16 (10)	C9—C10—H10	119.8
C4—C5—H5	108.5	C11—C10—H10	119.8
C6—C5—H5	108.5	C10—C11—C12	120.01 (15)
S1—C5—H5	108.5	C10—C11—H11	120.0
C5—C6—H6A	109.5	C12—C11—H11	120.0
C5—C6—H6B	109.5	C7—C12—C11	118.64 (14)
H6A—C6—H6B	109.5	C7—C12—H12	120.7
C5—C6—H6C	109.5	C11—C12—H12	120.7

C4—N3—C2—S2	−178.34 (11)	C2—S1—C5—C4	−0.78 (10)
C7—N3—C2—S2	4.66 (19)	C2—S1—C5—C6	−124.12 (11)
C4—N3—C2—S1	1.17 (15)	C2—N3—C7—C12	−102.04 (16)
C7—N3—C2—S1	−175.83 (10)	C4—N3—C7—C12	81.04 (17)
C5—S1—C2—N3	−0.14 (11)	C2—N3—C7—C8	81.10 (18)
C5—S1—C2—S2	179.39 (9)	C4—N3—C7—C8	−95.83 (16)
C2—N3—C4—O1	177.98 (14)	C12—C7—C8—C9	0.2 (2)
C7—N3—C4—O1	−4.9 (2)	N3—C7—C8—C9	177.02 (13)
C2—N3—C4—C5	−1.81 (17)	C7—C8—C9—C10	0.8 (2)
C7—N3—C4—C5	175.29 (12)	C8—C9—C10—C11	−1.1 (2)
O1—C4—C5—C6	−54.3 (2)	C9—C10—C11—C12	0.5 (2)
N3—C4—C5—C6	125.48 (13)	C8—C7—C12—C11	−0.8 (2)
O1—C4—C5—S1	−178.26 (13)	N3—C7—C12—C11	−177.60 (13)
N3—C4—C5—S1	1.53 (14)	C10—C11—C12—C7	0.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	1.00	2.47	3.4321 (16)	162

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₉NOS₂
M_r	223.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	153
a, b, c (Å)	6.8527 (4), 8.6643 (5), 17.5572 (15)
V (Å³)	1042.44 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.30 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2008)
T_min, T_max	0.872, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	9028, 2777, 2561
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.064, 1.00
No. of reflections	2777
No. of parameters	128
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.17
Absolute structure	Flack (1983), 1155 Friedel pairs
Absolute structure parameter	−0.01 (6)

Computer programs: CrystalClear (Rigaku/MSC, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	1.00	2.47	3.4321 (16)	162

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

We are very grateful to the Foundation of Taizhou Vocational and Technical College (grant No. 2010ZD09) for financial support.

References

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o34

doi:10.1107/S1600536811051312

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