(5Z)-5-(2-Hy­droxy­benzyl­idene)-3-(4-methyl­phen­yl)-2-sulfanyl­idene-1,3-thia­zolidin-4-one

Shahwar, D.; Tahir, M.N.; Kashif, M.; Saeed, A.; Bukhari, S.

doi:10.1107/S1600536812021630

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1818

doi:10.1107/S1600536812021630

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(5Z)-5-(2-Hydroxybenzylidene)-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one

Durre Shahwar,^a M. Nawaz Tahir,^b ^* Misbah Kashif,^a Afifa Saeed ^a and Sana Bukhari ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 11 May 2012; accepted 13 May 2012; online 19 May 2012)

In the title compound, C₁₇H₁₃NO₂S₂, the dihedral angles between the 2-sulfanylidene-1,3-thiazolidin-4-one group and the pendant toluene and 2-hydroxybenzene rings are 74.62 (6) and 8.73 (12)°, respectively. An intramolecular C—H⋯S interaction occurs. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(16) loops. This link is reinforced by a pair of C—H⋯O hydrogen bonds. The dimers are connected by weak C—H⋯S interactions.

Related literature

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

Experimental

Crystal data

C₁₇H₁₃NO₂S₂
M_r = 327.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.101
S = 0.93
2801 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x+1, -y+2, -z; (ii) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021630/hb6792sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812021630/hb6792Isup3.cml

checkCIF report

Comment top

In the search for new enzyme inhibitors, a series of rohdanine derivatives were prepared and their crystal structures have been reported such as (5Z)-5-(2-hydroxybenzylidene)-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one (Shahwar et al., 2009a) and (5Z)-5-(2-methylbenzylidene)-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one (Shahwar et al., 2009b) which are related to the title compound, (I), (Fig. 1).

In (I), the toluene group A (C1–C7), group B (N1/C8/S1/C10/C9/O1/S2) of 2-sulfanylidene-1,3-thiazolidin-4-one and group C (C11–C17/O2) of 2-methylphenol are planar with r. m. s. deviation of 0.0246 Å, 0.0186 Å and 0.0175 Å, respectively. The dihedral angle between A/B, A/C and B/C is 74.62 (6), 70.16 (7) and 8.73 (12)°, respectively. The molecules are dimerized due to strong O—H···O type of H-bonding with R₂²(16) (Bernstein et al., 1995) ring motifs (Table 1, Fig. 2). R₂²(7) ring motifs are formed within the dimers when weak H-boding of C—H···O type is considered. The dimers are interlinked due to C—H···S type of H-bondings (Table 1, Fig. 2).

Related literature top

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

Experimental top

3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one (0.419 g, 0.2 mol) (prepared according to the method: Shahwar et al. 2009a), 2-hydroxybenzaldehyde (0.244 g, 0.2 mol) and K₂CO₃ (0.553 g, 0.4 mol) were dissolved in distilled water (10 ml) and continuously stirred for 24 h. The mixture was neutralized with 5% HCl and the crude product obtained was recrysrallized in ethylacetate to get the yellow needles of (I).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, showing that molecules form dimers with R₂²(16) and other ring motifs.

(5Z)-5-(2-Hydroxybenzylidene)-3-(4-methylphenyl)-2-sulfanylidene-1,3- thiazolidin-4-one top

Crystal data top

C₁₇H₁₃NO₂S₂	F(000) = 680
M_r = 327.40	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.3°, θ_min = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.945, T_max = 0.965	l = −25→25
10652 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0385P)²] where P = (F_o² + 2F_c²)/3
2801 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₃NO₂S₂	V = 1547.54 (13) Å³
M_r = 327.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8258 (6) Å	µ = 0.35 mm⁻¹
b = 5.4278 (3) Å	T = 296 K
c = 21.0715 (9) Å	0.35 × 0.15 × 0.13 mm
β = 101.857 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2801 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1473 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.965	R_int = 0.069
10652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 0.93	Δρ_max = 0.19 e Å⁻³
2801 reflections	Δρ_min = −0.26 e Å⁻³
201 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NO₂S₂
M_r	327.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.8258 (6), 5.4278 (3), 21.0715 (9)
β (°)	101.857 (3)
V (Å³)	1547.54 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.35 × 0.15 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.945, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	10652, 2801, 1473
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.101, 0.93
No. of reflections	2801
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z; (ii) x, y+1, z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Shahwar, D., Tahir, M. N., Raza, M. A. & Iqbal, B. (2009a). Acta Cryst. E65, o2903. Web of Science CrossRef IUCr Journals Google Scholar
Shahwar, D., Tahir, M. N., Raza, M. A. & Iqbal, B. (2009b). Acta Cryst. E65, o2917. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1818

doi:10.1107/S1600536812021630

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(5Z)-5-(2-Hy­dr­oxy­benzyl­­idene)-3-(4-methyl­phen­yl)-2-sulfanyl­­idene-1,3-thia­zolidin-4-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

(5Z)-5-(2-Hydroxybenzylidene)-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one