(5Z)-5-(2-Hy-droxy-benzyl-idene)-3-(4-methyl-phen-yl)-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

In the title compound, C(17)H(13)NO(2)S(2), the dihedral angles between the 2-sulfanyl-idene-1,3-thia-zolidin-4-one group and the pendant toluene and 2-hy-droxy-benzene rings are 74.62 (6) and 8.73 (12)°, respectively. An intra-molecular C-H⋯S inter-action occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(16) loops. This link is reinforced by a pair of C-H⋯O hydrogen bonds. The dimers are connected by weak C-H⋯S inter-actions.

Related literature

For related structures and further synthetic details, see: Shahwar et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H13NO2S2

M = 327.40

Monoclinic,

a = 13.8258 (6) Å

b = 5.4278 (3) Å

c = 21.0715 (9) Å

β = 101.857 (3)°

V = 1547.54 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.35 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.945, T max = 0.965

10652 measured reflections

2801 independent reflections

1473 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.101

S = 0.93

2801 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021630/hb6792sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021630/hb6792Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021630/hb6792Isup3.cml

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

C17H13NO2S2	F(000) = 680
Mr = 327.40	Dx = 1.405 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1473 reflections
a = 13.8258 (6) Å	θ = 3.0–25.3°
b = 5.4278 (3) Å	µ = 0.35 mm−1
c = 21.0715 (9) Å	T = 296 K
β = 101.857 (3)°	Needle, yellow
V = 1547.54 (13) Å3	0.35 × 0.15 × 0.13 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.20 pixels mm-1	θmax = 25.3°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.945, Tmax = 0.965	l = −25→25
10652 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0385P)2] where P = (Fo2 + 2Fc2)/3
2801 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
S1	0.32730 (6)	0.24641 (18)	0.08942 (4)	0.0555 (3)
S2	0.14244 (6)	−0.0283 (2)	0.04718 (4)	0.0633 (4)
O1	0.28996 (14)	0.6397 (4)	−0.06441 (10)	0.0510 (8)
O2	0.57469 (16)	1.0037 (5)	0.06997 (10)	0.0773 (10)
N1	0.21224 (16)	0.3302 (5)	−0.02022 (11)	0.0383 (9)
C1	0.1268 (2)	0.3173 (6)	−0.07351 (14)	0.0387 (11)
C2	0.1162 (2)	0.1227 (7)	−0.11500 (14)	0.0486 (13)
C3	0.0316 (2)	0.1030 (7)	−0.16312 (14)	0.0531 (14)
C4	−0.0423 (2)	0.2766 (7)	−0.16993 (15)	0.0486 (13)
C5	−0.0286 (2)	0.4723 (7)	−0.12792 (17)	0.0598 (14)
C6	0.0553 (2)	0.4943 (7)	−0.07940 (15)	0.0534 (12)
C7	−0.1379 (2)	0.2463 (7)	−0.21949 (16)	0.0805 (16)
C8	0.2200 (2)	0.1799 (6)	0.03366 (14)	0.0436 (11)
C9	0.2879 (2)	0.5003 (7)	−0.01944 (15)	0.0404 (11)
C10	0.3612 (2)	0.4829 (6)	0.04263 (13)	0.0408 (10)
C11	0.4379 (2)	0.6400 (6)	0.05800 (13)	0.0418 (11)
C12	0.5128 (2)	0.6614 (6)	0.11718 (13)	0.0391 (11)
C13	0.5208 (2)	0.5059 (7)	0.17093 (14)	0.0530 (14)
C14	0.5919 (2)	0.5422 (7)	0.22614 (15)	0.0592 (14)
C15	0.6561 (2)	0.7355 (7)	0.22960 (15)	0.0564 (14)
C16	0.6513 (2)	0.8925 (7)	0.17828 (15)	0.0520 (13)
C17	0.5808 (2)	0.8546 (6)	0.12202 (14)	0.0446 (11)
H2	0.16539	0.00361	−0.11109	0.0582*
H2A	0.62157	1.09941	0.07623	0.0928*
H3	0.02469	−0.03032	−0.19141	0.0637*
H5	−0.07693	0.59368	−0.13213	0.0718*
H6	0.06290	0.62792	−0.05118	0.0641*
H7A	−0.12882	0.12593	−0.25115	0.1208*
H7B	−0.15615	0.40109	−0.24058	0.1208*
H7C	−0.18916	0.19251	−0.19813	0.1208*
H11	0.44377	0.75226	0.02568	0.0501*
H13	0.47704	0.37487	0.16928	0.0640*
H14	0.59639	0.43528	0.26110	0.0709*
H15	0.70355	0.76061	0.26727	0.0677*
H16	0.69516	1.02395	0.18109	0.0625*

	U11	U22	U33	U12	U13	U23
S1	0.0601 (5)	0.0596 (7)	0.0403 (5)	−0.0257 (5)	−0.0047 (4)	0.0102 (5)
S2	0.0689 (6)	0.0671 (8)	0.0527 (5)	−0.0349 (6)	0.0096 (4)	0.0025 (5)
O1	0.0484 (13)	0.0539 (16)	0.0449 (13)	−0.0174 (12)	−0.0037 (11)	0.0132 (13)
O2	0.0795 (18)	0.087 (2)	0.0509 (14)	−0.0543 (16)	−0.0205 (12)	0.0243 (16)
N1	0.0362 (14)	0.0385 (18)	0.0362 (14)	−0.0112 (14)	−0.0015 (12)	0.0016 (14)
C1	0.0347 (17)	0.041 (2)	0.0385 (18)	−0.0079 (18)	0.0031 (15)	0.0005 (18)
C2	0.0429 (19)	0.053 (3)	0.0473 (19)	0.0042 (19)	0.0032 (17)	−0.006 (2)
C3	0.057 (2)	0.056 (3)	0.0422 (19)	−0.011 (2)	0.0009 (18)	−0.0158 (19)
C4	0.0417 (19)	0.056 (3)	0.0441 (19)	−0.011 (2)	−0.0002 (16)	0.011 (2)
C5	0.049 (2)	0.050 (3)	0.075 (2)	0.006 (2)	0.000 (2)	0.007 (2)
C6	0.053 (2)	0.043 (2)	0.060 (2)	−0.005 (2)	0.0019 (18)	−0.013 (2)
C7	0.055 (2)	0.112 (4)	0.061 (2)	−0.014 (2)	−0.0196 (18)	0.012 (3)
C8	0.0447 (18)	0.044 (2)	0.0401 (18)	−0.0132 (18)	0.0042 (15)	−0.0036 (18)
C9	0.0370 (18)	0.040 (2)	0.0431 (19)	−0.0070 (18)	0.0054 (16)	−0.0045 (19)
C10	0.0372 (17)	0.047 (2)	0.0363 (17)	−0.0089 (18)	0.0032 (14)	0.0034 (18)
C11	0.0417 (18)	0.044 (2)	0.0374 (17)	−0.0101 (18)	0.0026 (15)	0.0061 (17)
C12	0.0345 (17)	0.042 (2)	0.0379 (18)	−0.0092 (18)	0.0007 (15)	0.0006 (18)
C13	0.052 (2)	0.053 (3)	0.047 (2)	−0.014 (2)	−0.0059 (17)	0.008 (2)
C14	0.064 (2)	0.061 (3)	0.044 (2)	−0.012 (2)	−0.0091 (18)	0.014 (2)
C15	0.056 (2)	0.066 (3)	0.0393 (19)	−0.008 (2)	−0.0089 (17)	−0.002 (2)
C16	0.0414 (18)	0.062 (3)	0.046 (2)	−0.0162 (19)	−0.0066 (16)	−0.002 (2)
C17	0.0452 (19)	0.047 (2)	0.0386 (18)	−0.0076 (19)	0.0016 (16)	0.0036 (19)

S1—C8	1.731 (3)	C12—C17	1.398 (4)
S1—C10	1.741 (3)	C12—C13	1.399 (4)
S2—C8	1.623 (3)	C13—C14	1.374 (4)
O1—C9	1.218 (4)	C14—C15	1.367 (5)
O2—C17	1.352 (4)	C15—C16	1.368 (5)
O2—H2A	0.8200	C16—C17	1.387 (4)
N1—C1	1.455 (4)	C2—H2	0.9300
N1—C9	1.393 (4)	C3—H3	0.9300
N1—C8	1.384 (4)	C5—H5	0.9300
C1—C2	1.360 (5)	C6—H6	0.9300
C1—C6	1.366 (5)	C7—H7A	0.9600
C2—C3	1.386 (4)	C7—H7B	0.9600
C3—C4	1.376 (5)	C7—H7C	0.9600
C4—C5	1.371 (5)	C11—H11	0.9300
C4—C7	1.516 (4)	C13—H13	0.9300
C5—C6	1.385 (4)	C14—H14	0.9300
C9—C10	1.484 (4)	C15—H15	0.9300
C10—C11	1.347 (4)	C16—H16	0.9300
C11—C12	1.453 (4)
C8—S1—C10	93.57 (14)	C14—C15—C16	120.7 (3)
C17—O2—H2A	109.00	C15—C16—C17	119.7 (3)
C1—N1—C8	121.2 (2)	O2—C17—C16	121.4 (3)
C1—N1—C9	122.0 (2)	C12—C17—C16	121.2 (3)
C8—N1—C9	116.7 (2)	O2—C17—C12	117.5 (3)
N1—C1—C6	119.6 (3)	C1—C2—H2	120.00
C2—C1—C6	120.5 (3)	C3—C2—H2	120.00
N1—C1—C2	119.8 (3)	C2—C3—H3	119.00
C1—C2—C3	119.6 (3)	C4—C3—H3	119.00
C2—C3—C4	121.4 (3)	C4—C5—H5	119.00
C3—C4—C7	121.4 (3)	C6—C5—H5	119.00
C5—C4—C7	121.0 (3)	C1—C6—H6	120.00
C3—C4—C5	117.5 (3)	C5—C6—H6	120.00
C4—C5—C6	121.8 (3)	C4—C7—H7A	109.00
C1—C6—C5	119.2 (3)	C4—C7—H7B	109.00
S1—C8—S2	122.09 (18)	C4—C7—H7C	109.00
S1—C8—N1	110.2 (2)	H7A—C7—H7B	109.00
S2—C8—N1	127.7 (2)	H7A—C7—H7C	109.00
O1—C9—N1	122.7 (3)	H7B—C7—H7C	110.00
O1—C9—C10	127.2 (3)	C10—C11—H11	115.00
N1—C9—C10	110.1 (3)	C12—C11—H11	115.00
S1—C10—C11	128.4 (2)	C12—C13—H13	119.00
C9—C10—C11	122.2 (3)	C14—C13—H13	119.00
S1—C10—C9	109.4 (2)	C13—C14—H14	120.00
C10—C11—C12	130.1 (3)	C15—C14—H14	120.00
C11—C12—C17	118.2 (3)	C14—C15—H15	120.00
C13—C12—C17	117.0 (3)	C16—C15—H15	120.00
C11—C12—C13	124.8 (3)	C15—C16—H16	120.00
C12—C13—C14	121.5 (3)	C17—C16—H16	120.00
C13—C14—C15	119.9 (3)
C10—S1—C8—S2	−177.0 (2)	C3—C4—C5—C6	−1.2 (5)
C10—S1—C8—N1	1.8 (2)	C7—C4—C5—C6	175.5 (3)
C8—S1—C10—C9	−2.5 (2)	C4—C5—C6—C1	0.5 (5)
C8—S1—C10—C11	174.7 (3)	O1—C9—C10—S1	−177.6 (3)
C8—N1—C1—C2	−73.7 (4)	O1—C9—C10—C11	5.0 (5)
C8—N1—C1—C6	102.9 (4)	N1—C9—C10—S1	2.6 (3)
C9—N1—C1—C2	109.1 (4)	N1—C9—C10—C11	−174.8 (3)
C9—N1—C1—C6	−74.3 (4)	S1—C10—C11—C12	−1.0 (5)
C1—N1—C8—S1	−177.9 (2)	C9—C10—C11—C12	175.9 (3)
C1—N1—C8—S2	0.9 (4)	C10—C11—C12—C13	2.8 (5)
C9—N1—C8—S1	−0.6 (3)	C10—C11—C12—C17	−175.5 (3)
C9—N1—C8—S2	178.2 (2)	C11—C12—C13—C14	−177.9 (3)
C1—N1—C9—O1	−3.8 (5)	C17—C12—C13—C14	0.4 (5)
C1—N1—C9—C10	176.0 (3)	C11—C12—C17—O2	−2.6 (4)
C8—N1—C9—O1	178.9 (3)	C11—C12—C17—C16	177.0 (3)
C8—N1—C9—C10	−1.4 (4)	C13—C12—C17—O2	179.0 (3)
N1—C1—C2—C3	175.8 (3)	C13—C12—C17—C16	−1.5 (4)
C6—C1—C2—C3	−0.7 (5)	C12—C13—C14—C15	0.7 (5)
N1—C1—C6—C5	−176.1 (3)	C13—C14—C15—C16	−0.8 (5)
C2—C1—C6—C5	0.5 (5)	C14—C15—C16—C17	−0.3 (5)
C1—C2—C3—C4	0.0 (5)	C15—C16—C17—O2	−179.0 (3)
C2—C3—C4—C5	1.0 (5)	C15—C16—C17—C12	1.4 (5)
C2—C3—C4—C7	−175.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.82	1.92	2.712 (3)	162
C6—H6···S2ii	0.93	2.84	3.736 (4)	163
C11—H11···O2i	0.93	2.38	3.294 (4)	167
C13—H13···S1	0.93	2.48	3.194 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.82	1.92	2.712 (3)	162
C6—H6⋯S2ii	0.93	2.84	3.736 (4)	163
C11—H11⋯O2i	0.93	2.38	3.294 (4)	167
C13—H13⋯S1	0.93	2.48	3.194 (3)	133

Symmetry codes: (i) ; (ii) .