3-Phenyl-2-thioxo-1,3-thia­zolidin-4-one

Zhu, F.-X.; Zhou, J.-F.; Gong, G.-X.

doi:10.1107/S1600536808030079

organic compounds

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Volume 64| Part 10| October 2008| Page o1998

doi:10.1107/S1600536808030079

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3-Phenyl-2-thioxo-1,3-thiazolidin-4-one

Feng-Xia Zhu,^a ^* Jian-Feng Zhou ^a and Gui-Xia Gong ^b

^aJiangsu Key Laboratory for the Chemistry of Low-dimensional Materials, Department of Chemistry, Huaiyin Teachers College, 111 West Changjiang Road, Huaian 223300, Jiangsu, People's Republic of China, and ^bKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou 215123, People's Republic of China
^*Correspondence e-mail: zhufengxia501@hotmail.com

(Received 3 September 2008; accepted 18 September 2008; online 24 September 2008)

In the molecule of the title compound, C₉H₇NOS₂, the heterocycle and the phenyl ring are oriented at a dihedral angle of 72.3 (1)°. Adjacent molecules are connected through C—H⋯O interactions.

Related literature

For the synthesis of 3-phenylrhodanine, see: Brown et al. (1956 ). For the therapeutic properties of rhodanine-based molecules, including anticonvulsant, antibacterial, antiviral and antidiabetic properties, see: Momose et al. (1991 ); HCV protease, Sudo et al. (1997 ); HCV NS3 protease, Sing et al. (2001 ); aldols reductase, Bruno et al. (2002 ); factor protease, Sherida et al. (2006 ).

Experimental

Crystal data

C₉H₇NOS₂
M_r = 209.28
Monoclinic, P 2₁ /c
a = 12.9941 (13) Å
b = 5.6111 (6) Å
c = 12.7271 (13) Å
β = 93.847 (3)°
V = 925.86 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 296 (2) K
0.20 × 0.15 × 0.05 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.91, T_max = 0.97
10918 measured reflections
1800 independent reflections
1146 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.080
S = 1.00
1800 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.51	3.410 (3)	163
C8—H8⋯O1ⁱⁱ	0.93	2.46	3.386 (3)	171
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030079/pk2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030079/pk2120Isup2.hkl

checkCIF report

Comment top

Rhodanine derivatives are attractive compounds owing to their outstanding biological activities. They have undergone rapid development as a result of their use in anticonvulsant, antibacterial, antiviral and antidiabetic treatments (Momose et al., 1991). As an extension of these studies, we report herein on the structure of 3-phenylrhodanine (3-phenyl-2-thioxothiazolidin-4-one).

A 3-phenylrhodanine molecule, which is the asymmetric unit of the structure, is shown in Fig. 1. All the bond distances and bond angles are within the normal ranges. The two parts of the molecule, the five-member heterocycle and the phenyl ring, are oriented at a dihedral angle of 72.3 (1)°. Adjacent molecules are connected through C–H—O hydrogen bonds (Table 1).

Related literature top

For the synthesis of 3-phenylrhodanine, see: Brown et al. (1956). For the therapeutic properties of rhodanine-based molecules, including anticonvulsant, antibacterial, antiviral and antidiabetic properties, see: Momose et al. (1991); HCV protease, Sudo et al. (1997); HCV NS3 protease, Sing et al. (2001); aldols reductase, Bruno et al. (2002); factor protease, Sherida et al. (2006).

Experimental top

3-phenylrhodanine was synthesized according to the literature (Brown et al., 1956), and was recrystallized using a mixed solvent of ether and 95% ethanol (1:1 by volume). Yellow sheet crystals are obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The asymmetric unit of 3-benzylrhodanine with atom labels and 50% probability displacement ellipsoids for non-H atoms.

3-Phenyl-2-thioxo-1,3-thiazolidin-4-one top

Crystal data top

C₉H₇NOS₂	F(000) = 432
M_r = 209.28	D_x = 1.501 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1321 reflections
a = 12.9941 (13) Å	θ = 3.1–21.1°
b = 5.6111 (6) Å	µ = 0.53 mm⁻¹
c = 12.7271 (13) Å	T = 296 K
β = 93.847 (3)°	Plate, yellow
V = 925.86 (17) Å³	0.20 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	1800 independent reflections
Radiation source: fine-focus sealed tube	1146 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
Detector resolution: 8 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −6→6
T_min = 0.91, T_max = 0.97	l = −15→15
10918 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0272P)² + 0.2182P] where P = (F_o² + 2F_c²)/3
1800 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₉H₇NOS₂	V = 925.86 (17) Å³
M_r = 209.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9941 (13) Å	µ = 0.53 mm⁻¹
b = 5.6111 (6) Å	T = 296 K
c = 12.7271 (13) Å	0.20 × 0.15 × 0.05 mm
β = 93.847 (3)°

Data collection top

Bruker APEXII diffractometer	1800 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1146 reflections with I > 2σ(I)
T_min = 0.91, T_max = 0.97	R_int = 0.066
10918 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
1800 reflections	Δρ_min = −0.23 e Å⁻³
118 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.35704 (19)	0.8242 (4)	0.64373 (18)	0.0412 (6)
C2	0.2485 (2)	0.5060 (4)	0.58348 (17)	0.0413 (6)
C3	0.32529 (19)	0.5020 (4)	0.50099 (19)	0.0495 (7)
H3A	0.2908	0.5231	0.4317	0.059*
H3B	0.3616	0.3508	0.5024	0.059*
C4	0.20680 (17)	0.7118 (4)	0.74476 (17)	0.0351 (6)
C5	0.13898 (18)	0.8984 (4)	0.74630 (18)	0.0433 (6)
H5	0.1376	1.0140	0.6938	0.052*
C6	0.07285 (19)	0.9134 (5)	0.8263 (2)	0.0478 (7)
H6	0.0262	1.0389	0.8275	0.057*
C7	0.0756 (2)	0.7437 (5)	0.90434 (19)	0.0484 (7)
H7	0.0309	0.7549	0.9582	0.058*
C8	0.1438 (2)	0.5586 (5)	0.90295 (19)	0.0512 (7)
H8	0.1455	0.4441	0.9559	0.061*
C9	0.21025 (19)	0.5414 (4)	0.82277 (18)	0.0444 (6)
H9	0.2569	0.4158	0.8216	0.053*
N1	0.27190 (14)	0.6844 (3)	0.65849 (14)	0.0364 (5)
O1	0.17588 (14)	0.3754 (3)	0.58706 (13)	0.0541 (5)
S1	0.41400 (5)	0.74161 (13)	0.52991 (6)	0.0566 (2)
S2	0.40143 (5)	1.03944 (13)	0.71931 (6)	0.0583 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0359 (15)	0.0436 (15)	0.0446 (14)	0.0026 (12)	0.0059 (11)	0.0053 (12)
C2	0.0456 (16)	0.0411 (15)	0.0378 (13)	0.0024 (13)	0.0066 (12)	0.0023 (12)
C3	0.0501 (16)	0.0522 (17)	0.0475 (14)	0.0041 (14)	0.0124 (12)	−0.0048 (13)
C4	0.0342 (14)	0.0356 (14)	0.0362 (12)	−0.0006 (11)	0.0077 (11)	−0.0010 (11)
C5	0.0440 (16)	0.0407 (15)	0.0458 (15)	0.0024 (13)	0.0069 (13)	0.0055 (11)
C6	0.0403 (16)	0.0461 (16)	0.0577 (16)	0.0089 (13)	0.0089 (13)	−0.0033 (13)
C7	0.0474 (16)	0.0539 (17)	0.0458 (14)	−0.0049 (15)	0.0182 (12)	−0.0063 (14)
C8	0.0614 (18)	0.0489 (16)	0.0445 (15)	−0.0046 (15)	0.0125 (14)	0.0097 (13)
C9	0.0497 (16)	0.0370 (14)	0.0472 (14)	0.0093 (12)	0.0090 (12)	0.0044 (12)
N1	0.0359 (12)	0.0356 (11)	0.0386 (11)	−0.0007 (9)	0.0088 (9)	−0.0003 (9)
O1	0.0594 (13)	0.0506 (11)	0.0532 (11)	−0.0147 (10)	0.0107 (9)	−0.0059 (9)
S1	0.0465 (4)	0.0673 (5)	0.0588 (4)	−0.0072 (4)	0.0228 (3)	−0.0061 (4)
S2	0.0511 (5)	0.0561 (5)	0.0682 (5)	−0.0128 (4)	0.0081 (4)	−0.0131 (4)

Geometric parameters (Å, º) top

C1—N1	1.379 (3)	C4—N1	1.439 (3)
C1—S2	1.626 (3)	C5—C6	1.378 (3)
C1—S1	1.733 (2)	C5—H5	0.9300
C2—O1	1.198 (3)	C6—C7	1.375 (3)
C2—N1	1.402 (3)	C6—H6	0.9300
C2—C3	1.496 (3)	C7—C8	1.366 (3)
C3—S1	1.793 (3)	C7—H7	0.9300
C3—H3A	0.9700	C8—C9	1.384 (3)
C3—H3B	0.9700	C8—H8	0.9300
C4—C5	1.370 (3)	C9—H9	0.9300
C4—C9	1.377 (3)

N1—C1—S2	126.73 (18)	C6—C5—H5	120.3
N1—C1—S1	110.68 (17)	C7—C6—C5	120.3 (2)
S2—C1—S1	122.59 (15)	C7—C6—H6	119.9
O1—C2—N1	123.1 (2)	C5—C6—H6	119.9
O1—C2—C3	125.5 (2)	C8—C7—C6	120.2 (2)
N1—C2—C3	111.4 (2)	C8—C7—H7	119.9
C2—C3—S1	107.11 (17)	C6—C7—H7	119.9
C2—C3—H3A	110.3	C7—C8—C9	120.0 (2)
S1—C3—H3A	110.3	C7—C8—H8	120.0
C2—C3—H3B	110.3	C9—C8—H8	120.0
S1—C3—H3B	110.3	C4—C9—C8	119.5 (2)
H3A—C3—H3B	108.5	C4—C9—H9	120.3
C5—C4—C9	120.7 (2)	C8—C9—H9	120.3
C5—C4—N1	120.3 (2)	C1—N1—C2	116.9 (2)
C9—C4—N1	118.9 (2)	C1—N1—C4	124.14 (19)
C4—C5—C6	119.4 (2)	C2—N1—C4	119.0 (2)
C4—C5—H5	120.3	C1—S1—C3	93.86 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.51	3.410 (3)	163
C8—H8···O1ⁱⁱ	0.93	2.46	3.386 (3)	171

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

Experimental details

Crystal data
Chemical formula	C₉H₇NOS₂
M_r	209.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.9941 (13), 5.6111 (6), 12.7271 (13)
β (°)	93.847 (3)
V (Å³)	925.86 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.20 × 0.15 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.91, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	10918, 1800, 1146
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.080, 1.00
No. of reflections	1800
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.51	3.410 (3)	163.2
C8—H8···O1ⁱⁱ	0.93	2.46	3.386 (3)	171.3

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

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1998

doi:10.1107/S1600536808030079

Open

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