3-[(5-Chloro-2-hy-droxy-benzyl-idene)amino]-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

In the title compound, C10H7ClN2O2S2, the mean plane of the thioxo-thia-zolidine ring [maximum deviation = 0.032 (2) Å] is inclined to the benzene ring by 12.25 (4)°. There is a strong intra-molecular O-H⋯N hydrogen bond present. In the crystal, mol-ecules are linked via pairs of C-H⋯Cl hydrogen bonds, forming inversion dimers.

Related literature

For general background to the chemistry, and pharmacological and biological activity of rhodanine and its derivatives, see: Raper (1985 ▶); Contello et al. (1994 ▶); Villain-Guillot et al. (2007 ▶); Yan et al. (2007 ▶); Kletzien et al. (1992 ▶).

Experimental

Crystal data

C10H7ClN2O2S2

M = 286.77

Monoclinic,

a = 9.8506 (3) Å

b = 10.0936 (3) Å

c = 12.1096 (4) Å

β = 110.409 (2)°

V = 1128.45 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 100 K

0.37 × 0.26 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.783, T max = 0.927

10564 measured reflections

2816 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.081

S = 1.09

2816 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016577/su2611sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016577/su2611Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016577/su2611Isup3.cml

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

C10H7ClN2O2S2	F(000) = 584
Mr = 286.77	Dx = 1.688 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4301 reflections
a = 9.8506 (3) Å	θ = 2.2–28.3°
b = 10.0936 (3) Å	µ = 0.70 mm−1
c = 12.1096 (4) Å	T = 100 K
β = 110.409 (2)°	Block, yellow
V = 1128.45 (6) Å3	0.37 × 0.26 × 0.11 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	2816 independent reflections
Radiation source: fine-focus sealed tube	2427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.783, Tmax = 0.927	k = −13→13
10564 measured reflections	l = −16→16

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.6866P] where P = (Fo2 + 2Fc2)/3
2816 reflections	(Δ/σ)max = 0.001
162 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	−0.07187 (4)	1.08989 (5)	0.26371 (4)	0.01535 (11)
S2	−0.06151 (4)	1.23019 (5)	0.48023 (4)	0.01547 (11)
O1	0.31445 (14)	0.95179 (13)	0.40194 (11)	0.0179 (3)
O2	0.25301 (14)	1.25062 (13)	0.75822 (11)	0.0163 (3)
H2	0.221 (3)	1.231 (2)	0.695 (2)	0.032 (7)*
N1	0.15074 (15)	1.07839 (14)	0.45427 (12)	0.0117 (3)
N2	0.23170 (15)	1.11112 (15)	0.56955 (12)	0.0129 (3)
C1	0.55038 (18)	1.01067 (18)	0.80910 (14)	0.0139 (3)
H1	0.5808	0.9404	0.7710	0.017*
C2	0.63231 (17)	1.04465 (18)	0.92291 (14)	0.0133 (3)
C3	0.59104 (18)	1.14826 (18)	0.98024 (14)	0.0147 (3)
H3	0.6496	1.1723	1.0582	0.018*
C4	0.46398 (19)	1.21576 (18)	0.92266 (15)	0.0155 (3)
H4	0.4350	1.2861	0.9617	0.019*
C5	0.37768 (18)	1.18186 (18)	0.80794 (14)	0.0135 (3)
C6	0.42240 (17)	1.07939 (17)	0.74940 (14)	0.0123 (3)
C7	0.34218 (18)	1.04111 (18)	0.62815 (15)	0.0143 (3)
H7	0.378 (2)	0.966 (2)	0.5974 (19)	0.019 (5)*
C8	0.01423 (18)	1.13498 (17)	0.40910 (14)	0.0129 (3)
C9	0.07577 (19)	0.98704 (19)	0.25954 (15)	0.0164 (4)
H9A	0.0442	0.8935	0.2455	0.020*
H9B	0.1092	1.0160	0.1952	0.020*
C10	0.19599 (19)	1.00064 (17)	0.37653 (15)	0.0136 (3)
Cl1	0.79051 (4)	0.95632 (4)	0.99429 (3)	0.01531 (11)

	U11	U22	U33	U12	U13	U23
S1	0.0133 (2)	0.0190 (2)	0.0114 (2)	−0.00020 (16)	0.00125 (16)	−0.00067 (16)
S2	0.0143 (2)	0.0150 (2)	0.0173 (2)	0.00122 (16)	0.00585 (16)	−0.00154 (16)
O1	0.0186 (6)	0.0198 (7)	0.0154 (6)	0.0049 (5)	0.0061 (5)	−0.0001 (5)
O2	0.0158 (6)	0.0176 (7)	0.0128 (6)	0.0054 (5)	0.0016 (5)	−0.0009 (5)
N1	0.0130 (7)	0.0106 (7)	0.0098 (6)	−0.0006 (5)	0.0020 (5)	−0.0005 (5)
N2	0.0131 (6)	0.0146 (8)	0.0098 (6)	−0.0020 (6)	0.0025 (5)	−0.0006 (5)
C1	0.0142 (8)	0.0152 (9)	0.0123 (8)	0.0004 (7)	0.0048 (6)	−0.0003 (6)
C2	0.0111 (7)	0.0147 (9)	0.0126 (8)	−0.0009 (6)	0.0023 (6)	0.0017 (6)
C3	0.0149 (8)	0.0172 (9)	0.0111 (7)	−0.0027 (7)	0.0033 (6)	−0.0020 (7)
C4	0.0165 (8)	0.0157 (9)	0.0144 (8)	0.0008 (7)	0.0054 (7)	−0.0019 (7)
C5	0.0126 (7)	0.0142 (9)	0.0137 (8)	0.0002 (7)	0.0047 (6)	0.0022 (6)
C6	0.0135 (8)	0.0112 (9)	0.0119 (8)	−0.0017 (6)	0.0039 (6)	−0.0006 (6)
C7	0.0152 (8)	0.0138 (9)	0.0134 (8)	−0.0011 (7)	0.0044 (6)	−0.0004 (7)
C8	0.0126 (8)	0.0129 (8)	0.0122 (7)	−0.0021 (6)	0.0030 (6)	0.0019 (6)
C9	0.0172 (8)	0.0186 (10)	0.0127 (8)	0.0002 (7)	0.0041 (7)	−0.0023 (7)
C10	0.0177 (8)	0.0110 (8)	0.0126 (8)	0.0000 (7)	0.0062 (6)	0.0022 (6)
Cl1	0.01286 (19)	0.0175 (2)	0.01301 (19)	0.00297 (15)	0.00127 (15)	0.00100 (15)

S1—C8	1.7277 (17)	C3—H3	0.9500
S1—C9	1.8018 (18)	C4—C3	1.381 (2)
S2—C8	1.6341 (17)	C4—C5	1.395 (2)
O1—C10	1.204 (2)	C4—H4	0.9500
O2—C5	1.355 (2)	C5—C6	1.409 (2)
O2—H2	0.74 (3)	C7—N2	1.284 (2)
N1—N2	1.3848 (19)	C7—C6	1.456 (2)
N1—C8	1.386 (2)	C7—H7	0.97 (2)
N1—C10	1.412 (2)	C9—C10	1.503 (2)
C1—C6	1.399 (2)	C9—H9A	0.9900
C1—H1	0.9500	C9—H9B	0.9900
C2—C1	1.376 (2)	Cl1—C2	1.7410 (17)
C2—C3	1.392 (2)
C8—S1—C9	93.79 (8)	C4—C5—C6	119.50 (16)
C5—O2—H2	109 (2)	C1—C6—C5	119.18 (15)
N2—N1—C8	115.97 (13)	C1—C6—C7	117.63 (15)
N2—N1—C10	126.87 (14)	C5—C6—C7	123.19 (16)
C8—N1—C10	117.03 (14)	N2—C7—C6	117.94 (16)
C7—N2—N1	120.33 (15)	N2—C7—H7	125.1 (13)
C2—C1—C6	120.14 (16)	C6—C7—H7	116.9 (13)
C2—C1—H1	119.9	S2—C8—S1	122.68 (10)
C6—C1—H1	119.9	N1—C8—S1	110.95 (12)
C1—C2—C3	121.03 (16)	N1—C8—S2	126.36 (13)
C1—C2—Cl1	118.72 (13)	S1—C9—H9A	110.2
C3—C2—Cl1	120.24 (13)	S1—C9—H9B	110.2
C2—C3—H3	120.3	C10—C9—S1	107.42 (12)
C4—C3—C2	119.31 (16)	C10—C9—H9A	110.2
C4—C3—H3	120.3	C10—C9—H9B	110.2
C3—C4—C5	120.79 (16)	H9A—C9—H9B	108.5
C3—C4—H4	119.6	O1—C10—N1	124.09 (16)
C5—C4—H4	119.6	O1—C10—C9	125.35 (16)
O2—C5—C4	117.39 (15)	N1—C10—C9	110.55 (14)
O2—C5—C6	123.12 (15)
C9—S1—C8—S2	−177.82 (12)	Cl1—C2—C1—C6	179.78 (13)
C9—S1—C8—N1	1.29 (13)	C1—C2—C3—C4	1.5 (3)
C8—S1—C9—C10	−3.74 (13)	Cl1—C2—C3—C4	−179.02 (13)
C8—N1—N2—C7	163.12 (15)	C5—C4—C3—C2	−0.5 (3)
C10—N1—N2—C7	−21.1 (2)	C3—C4—C5—O2	178.56 (15)
N2—N1—C8—S1	178.09 (11)	C3—C4—C5—C6	−1.4 (3)
N2—N1—C8—S2	−2.8 (2)	O2—C5—C6—C1	−177.81 (15)
C10—N1—C8—S1	1.86 (18)	O2—C5—C6—C7	2.7 (3)
C10—N1—C8—S2	−179.07 (13)	C4—C5—C6—C1	2.1 (2)
N2—N1—C10—O1	0.0 (3)	C4—C5—C6—C7	−177.44 (16)
N2—N1—C10—C9	179.45 (15)	C6—C7—N2—N1	−179.40 (14)
C8—N1—C10—O1	175.75 (16)	N2—C7—C6—C1	−174.04 (16)
C8—N1—C10—C9	−4.8 (2)	N2—C7—C6—C5	5.5 (3)
C2—C1—C6—C5	−1.1 (2)	S1—C9—C10—O1	−175.28 (15)
C2—C1—C6—C7	178.51 (15)	S1—C9—C10—N1	5.26 (17)
C3—C2—C1—C6	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.75 (2)	1.97 (2)	2.6291 (19)	147 (3)
C9—H9B···Cl1i	0.99	2.81	3.7860 (19)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.75 (2)	1.97 (2)	2.6291 (19)	147 (3)
C9—H9B⋯Cl1i	0.99	2.81	3.7860 (19)	169

Symmetry code: (i) .