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

Abstract

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,

• a = 12.9941 (13) Å

• b = 5.6111 (6) Å

• c = 12.7271 (13) Å

• β = 93.847 (3)°

• V = 925.86 (17) ų

• 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[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 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

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 ▶).

Supplementary Material

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
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) ; (ii) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All non-hydrogen atoms were found in Fourier maps, and were refined anisotropically. Hydrogen atoms were positioned geometrically, and the isotropic vibration parameters related to the atoms which they are bonded to with U_iso = 1.2 U_eq.

Figures

Fig. 1.

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

Crystal data

C9H7NOS2	F(000) = 432
Mr = 209.28	Dx = 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

Bruker APEXII diffractometer	1800 independent reflections
Radiation source: fine-focus sealed tube	1146 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 8 pixels mm-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −6→6
Tmin = 0.91, Tmax = 0.97	l = −15→15
10918 measured reflections

Refinement

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(Fo2) + (0.0272P)2 + 0.2182P] where P = (Fo2 + 2Fc2)/3
1800 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.