Methyl 2-((2Z,5Z)-2-{(E)-2-[1-(4-hy-droxy-phen-yl)ethyl-idene]hydrazin-1-yl-idene}-4-oxo-3-phenyl-1,3-thia-zolidin-5-yl-idene)acetate.

In the title compound, C20H17N3O4S, all non-H atoms, except those of the phenyl ring, are approximately coplanar [maximum deviation = 0.2214 (1) Å], and the dihedral angle between their best plane and the benzene ring is 53.13 (1)°. A short intra-molecular O⋯S contact of 2.838 (1) Å is formed between the ester carbonyl O atom and the S atom of the thia-zolidine ring. In the crystal, mol-ecules associated via O-H⋯O, C-H⋯O and C-H⋯S hydrogen bonds form layers parallel to (010), with only C-H⋯O-type short contacts between the mol-ecules in adjacent layers.

Related literature

For the biological activity of 4-thia­zolidinones, see: Dayam et al. (2006 ▶); Srivastava et al. (2005 ▶), Look et al. (1996 ▶), Barreca et al. (2001 ▶); Diurno et al. (1992 ▶).

Experimental

Crystal data

C20H17N3O4S

M = 395.42

Monoclinic,

a = 9.5049 (9) Å

b = 20.656 (2) Å

c = 10.1364 (10) Å

β = 107.637 (1)°

V = 1896.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 150 K

0.19 × 0.11 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.82, T max = 0.99

16907 measured reflections

4582 independent reflections

3740 reflections with i > 2σ(i)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.06

4582 reflections

259 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (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) global, I. DOI: 10.1107/S1600536813025270/gk2589sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025270/gk2589Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025270/gk2589Isup3.cml

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

C20H17N3O4S	F(000) = 824
Mr = 395.42	Dx = 1.385 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8755 reflections
a = 9.5049 (9) Å	θ = 2.3–28.6°
b = 20.656 (2) Å	µ = 0.20 mm−1
c = 10.1364 (10) Å	T = 150 K
β = 107.637 (1)°	Plate, clear yellow
V = 1896.6 (3) Å3	0.19 × 0.11 × 0.05 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4582 independent reflections
Radiation source: fine-focus sealed tube	3740 reflections with i > 2σ(i)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.3660 pixels mm-1	θmax = 28.7°, θmin = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −27→27
Tmin = 0.82, Tmax = 0.99	l = −13→13
16907 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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	W = 1/[Σ2(FO2) + (0.0643P)2 + 0.3949P] WHERE P = (FO2 + 2FC2)/3
S = 1.06	(Δ/σ)max = 0.001
4582 reflections	Δρmax = 0.34 e Å−3
259 parameters	Δρmin = −0.44 e Å−3
0 restraints

Experimental. The diffraction data were collected in three sets of 606 frames (0.3° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	1.01222 (4)	0.18869 (2)	0.39033 (4)	0.0203 (1)
O1	1.40358 (11)	0.26023 (5)	0.52637 (11)	0.0240 (3)
O2	1.09079 (13)	0.05575 (6)	0.42140 (13)	0.0347 (4)
O3	1.32263 (14)	0.02111 (6)	0.52834 (14)	0.0378 (4)
O4	0.14035 (12)	0.15348 (6)	0.10230 (13)	0.0285 (3)
N1	1.16412 (13)	0.29748 (6)	0.43935 (12)	0.0189 (3)
N2	0.90771 (13)	0.31123 (6)	0.34670 (13)	0.0222 (4)
N3	0.77907 (13)	0.27335 (6)	0.30473 (13)	0.0219 (4)
C1	1.27118 (16)	0.25046 (7)	0.47990 (15)	0.0190 (4)
C2	1.20296 (16)	0.18459 (7)	0.45802 (14)	0.0193 (4)
C3	1.01955 (15)	0.27395 (7)	0.38850 (14)	0.0190 (4)
C4	1.28646 (17)	0.13149 (7)	0.49043 (16)	0.0229 (4)
C5	1.22088 (18)	0.06672 (8)	0.47422 (16)	0.0260 (5)
C6	1.2661 (3)	−0.04389 (9)	0.5273 (3)	0.0553 (8)
C7	1.20015 (15)	0.36539 (7)	0.44261 (16)	0.0206 (4)
C8	1.29110 (17)	0.39165 (8)	0.56415 (17)	0.0275 (5)
C9	1.3342 (2)	0.45594 (9)	0.5655 (2)	0.0368 (5)
C10	1.2839 (2)	0.49351 (8)	0.4477 (2)	0.0384 (6)
C11	1.1899 (2)	0.46687 (8)	0.32791 (19)	0.0347 (5)
C12	1.14814 (18)	0.40248 (8)	0.32417 (16)	0.0272 (5)
C13	0.65717 (16)	0.30559 (7)	0.27572 (15)	0.0196 (4)
C14	0.64599 (17)	0.37782 (8)	0.28058 (17)	0.0260 (5)
C15	0.52047 (15)	0.26621 (7)	0.23315 (15)	0.0187 (4)
C16	0.52602 (16)	0.19872 (7)	0.23265 (17)	0.0241 (4)
C17	0.39928 (17)	0.16202 (8)	0.18891 (18)	0.0267 (5)
C18	0.26171 (16)	0.19204 (7)	0.14442 (15)	0.0207 (4)
C19	0.25339 (16)	0.25898 (7)	0.14520 (16)	0.0227 (4)
C20	0.38175 (16)	0.29540 (7)	0.18934 (16)	0.0221 (4)
H4	1.39070	0.13580	0.52480	0.0270*
H4O	0.066 (2)	0.1774 (11)	0.077 (2)	0.046 (6)*
H6A	1.19470	−0.04490	0.57960	0.0830*
H6B	1.34780	−0.07350	0.56990	0.0830*
H6C	1.21740	−0.05730	0.43150	0.0830*
H8	1.32360	0.36600	0.64560	0.0330*
H9	1.39860	0.47420	0.64770	0.0440*
H10	1.31370	0.53750	0.44900	0.0460*
H11	1.15380	0.49300	0.24760	0.0420*
H12	1.08480	0.38410	0.24160	0.0330*
H14A	0.74530	0.39660	0.31100	0.0390*
H14B	0.59250	0.38990	0.34570	0.0390*
H14C	0.59280	0.39420	0.18820	0.0390*
H16	0.61910	0.17760	0.26310	0.0290*
H17	0.40570	0.11610	0.18910	0.0320*
H19	0.16000	0.27990	0.11560	0.0270*
H20	0.37500	0.34130	0.18970	0.0260*

	U11	U22	U33	U12	U13	U23
S1	0.0149 (2)	0.0209 (2)	0.0233 (2)	−0.0034 (1)	0.0030 (1)	−0.0019 (1)
O1	0.0134 (5)	0.0242 (6)	0.0308 (6)	−0.0009 (4)	0.0011 (4)	0.0019 (4)
O2	0.0316 (7)	0.0275 (6)	0.0427 (7)	−0.0071 (5)	0.0078 (5)	−0.0030 (5)
O3	0.0387 (7)	0.0198 (6)	0.0525 (8)	0.0051 (5)	0.0104 (6)	0.0035 (5)
O4	0.0159 (5)	0.0239 (6)	0.0441 (7)	−0.0016 (5)	0.0067 (5)	−0.0074 (5)
N1	0.0131 (6)	0.0191 (6)	0.0222 (6)	−0.0025 (5)	0.0017 (5)	−0.0002 (5)
N2	0.0141 (6)	0.0247 (7)	0.0252 (7)	−0.0007 (5)	0.0022 (5)	−0.0009 (5)
N3	0.0137 (6)	0.0252 (7)	0.0250 (7)	−0.0005 (5)	0.0030 (5)	0.0008 (5)
C1	0.0158 (7)	0.0215 (7)	0.0187 (7)	−0.0012 (5)	0.0036 (5)	0.0005 (5)
C2	0.0180 (7)	0.0220 (7)	0.0172 (7)	−0.0034 (6)	0.0043 (5)	−0.0011 (5)
C3	0.0147 (7)	0.0220 (7)	0.0186 (7)	−0.0026 (5)	0.0025 (5)	−0.0012 (5)
C4	0.0193 (7)	0.0236 (8)	0.0242 (7)	0.0000 (6)	0.0044 (6)	−0.0009 (6)
C5	0.0294 (8)	0.0222 (8)	0.0273 (8)	0.0005 (6)	0.0101 (7)	−0.0014 (6)
C6	0.0658 (15)	0.0195 (9)	0.0817 (17)	0.0013 (9)	0.0238 (13)	0.0051 (10)
C7	0.0153 (6)	0.0181 (7)	0.0273 (8)	−0.0001 (5)	0.0050 (6)	−0.0002 (6)
C8	0.0230 (8)	0.0242 (8)	0.0296 (8)	0.0001 (6)	−0.0005 (6)	0.0014 (6)
C9	0.0334 (9)	0.0251 (9)	0.0423 (10)	−0.0044 (7)	−0.0031 (8)	−0.0061 (7)
C10	0.0401 (10)	0.0182 (8)	0.0524 (12)	−0.0038 (7)	0.0071 (9)	0.0001 (7)
C11	0.0408 (10)	0.0246 (8)	0.0354 (9)	0.0018 (7)	0.0066 (8)	0.0074 (7)
C12	0.0283 (8)	0.0242 (8)	0.0251 (8)	−0.0008 (6)	0.0023 (6)	−0.0004 (6)
C13	0.0157 (7)	0.0239 (8)	0.0185 (7)	0.0017 (6)	0.0041 (5)	0.0016 (5)
C14	0.0198 (7)	0.0224 (8)	0.0344 (9)	0.0006 (6)	0.0060 (6)	−0.0006 (6)
C15	0.0143 (7)	0.0228 (7)	0.0190 (7)	0.0009 (5)	0.0051 (5)	0.0017 (5)
C16	0.0151 (7)	0.0232 (8)	0.0334 (8)	0.0042 (6)	0.0065 (6)	0.0029 (6)
C17	0.0206 (8)	0.0191 (7)	0.0409 (9)	0.0027 (6)	0.0099 (7)	−0.0003 (6)
C18	0.0162 (7)	0.0234 (8)	0.0230 (7)	−0.0013 (6)	0.0069 (6)	−0.0028 (6)
C19	0.0147 (7)	0.0249 (8)	0.0270 (8)	0.0044 (6)	0.0041 (6)	0.0003 (6)
C20	0.0171 (7)	0.0195 (7)	0.0289 (8)	0.0032 (6)	0.0059 (6)	0.0015 (6)

S1—C2	1.7352 (16)	C13—C15	1.482 (2)
S1—C3	1.7628 (15)	C15—C20	1.394 (2)
O1—C1	1.2195 (19)	C15—C16	1.395 (2)
O2—C5	1.211 (2)	C16—C17	1.378 (2)
O3—C5	1.343 (2)	C17—C18	1.393 (2)
O3—C6	1.445 (2)	C18—C19	1.385 (2)
O4—C18	1.360 (2)	C19—C20	1.387 (2)
O4—H4O	0.84 (2)	C4—H4	0.9500
N1—C1	1.376 (2)	C6—H6A	0.9800
N1—C7	1.4420 (19)	C6—H6B	0.9800
N1—C3	1.4003 (19)	C6—H6C	0.9800
N2—N3	1.4046 (18)	C8—H8	0.9500
N2—C3	1.2766 (19)	C9—H9	0.9500
N3—C13	1.291 (2)	C10—H10	0.9500
C1—C2	1.495 (2)	C11—H11	0.9500
C2—C4	1.335 (2)	C12—H12	0.9500
C4—C5	1.464 (2)	C14—H14A	0.9800
C7—C12	1.383 (2)	C14—H14B	0.9800
C7—C8	1.384 (2)	C14—H14C	0.9800
C8—C9	1.389 (3)	C16—H16	0.9500
C9—C10	1.382 (3)	C17—H17	0.9500
C10—C11	1.385 (3)	C19—H19	0.9500
C11—C12	1.385 (2)	C20—H20	0.9500
C13—C14	1.498 (2)
C2—S1—C3	90.75 (7)	O4—C18—C17	117.69 (13)
C5—O3—C6	115.39 (17)	O4—C18—C19	122.83 (14)
C18—O4—H4O	107.9 (15)	C17—C18—C19	119.48 (14)
C1—N1—C3	114.79 (12)	C18—C19—C20	119.81 (14)
C3—N1—C7	123.08 (12)	C15—C20—C19	121.51 (13)
C1—N1—C7	122.05 (13)	C2—C4—H4	119.00
N3—N2—C3	108.99 (12)	C5—C4—H4	119.00
N2—N3—C13	114.87 (12)	O3—C6—H6A	109.00
O1—C1—C2	123.95 (14)	O3—C6—H6B	109.00
N1—C1—C2	110.48 (13)	O3—C6—H6C	109.00
O1—C1—N1	125.57 (14)	H6A—C6—H6B	110.00
S1—C2—C4	127.54 (12)	H6A—C6—H6C	109.00
C1—C2—C4	120.83 (14)	H6B—C6—H6C	109.00
S1—C2—C1	111.63 (11)	C7—C8—H8	120.00
S1—C3—N2	125.07 (12)	C9—C8—H8	120.00
N1—C3—N2	122.57 (13)	C8—C9—H9	120.00
S1—C3—N1	112.36 (10)	C10—C9—H9	120.00
C2—C4—C5	121.46 (15)	C9—C10—H10	120.00
O2—C5—O3	124.20 (16)	C11—C10—H10	120.00
O2—C5—C4	124.31 (15)	C10—C11—H11	120.00
O3—C5—C4	111.46 (14)	C12—C11—H11	120.00
N1—C7—C12	119.94 (14)	C7—C12—H12	121.00
C8—C7—C12	121.22 (14)	C11—C12—H12	121.00
N1—C7—C8	118.80 (13)	C13—C14—H14A	109.00
C7—C8—C9	119.12 (15)	C13—C14—H14B	109.00
C8—C9—C10	120.31 (17)	C13—C14—H14C	109.00
C9—C10—C11	119.78 (16)	H14A—C14—H14B	110.00
C10—C11—C12	120.59 (16)	H14A—C14—H14C	109.00
C7—C12—C11	118.95 (15)	H14B—C14—H14C	109.00
N3—C13—C15	115.50 (13)	C15—C16—H16	119.00
C14—C13—C15	119.45 (13)	C17—C16—H16	119.00
N3—C13—C14	125.05 (14)	C16—C17—H17	120.00
C13—C15—C20	121.09 (13)	C18—C17—H17	120.00
C16—C15—C20	117.65 (14)	C18—C19—H19	120.00
C13—C15—C16	121.25 (14)	C20—C19—H19	120.00
C15—C16—C17	121.37 (15)	C15—C20—H20	119.00
C16—C17—C18	120.18 (15)	C19—C20—H20	119.00
C3—S1—C2—C1	0.49 (11)	S1—C2—C4—C5	−1.6 (2)
C3—S1—C2—C4	179.93 (14)	C1—C2—C4—C5	177.79 (14)
C2—S1—C3—N1	−0.41 (11)	C2—C4—C5—O2	6.1 (3)
C2—S1—C3—N2	179.83 (13)	C2—C4—C5—O3	−172.43 (14)
C6—O3—C5—O2	−3.4 (3)	N1—C7—C8—C9	175.77 (15)
C6—O3—C5—C4	175.15 (17)	C12—C7—C8—C9	−2.0 (3)
C3—N1—C1—O1	179.63 (14)	N1—C7—C12—C11	−176.95 (15)
C3—N1—C1—C2	0.14 (17)	C8—C7—C12—C11	0.8 (3)
C7—N1—C1—O1	2.8 (2)	C7—C8—C9—C10	1.5 (3)
C7—N1—C1—C2	−176.72 (12)	C8—C9—C10—C11	0.1 (3)
C1—N1—C3—S1	0.22 (15)	C9—C10—C11—C12	−1.3 (3)
C1—N1—C3—N2	179.98 (14)	C10—C11—C12—C7	0.9 (3)
C7—N1—C3—S1	177.05 (11)	N3—C13—C15—C16	3.4 (2)
C7—N1—C3—N2	−3.2 (2)	N3—C13—C15—C20	−175.24 (14)
C1—N1—C7—C8	−52.6 (2)	C14—C13—C15—C16	−177.37 (14)
C1—N1—C7—C12	125.14 (16)	C14—C13—C15—C20	4.0 (2)
C3—N1—C7—C8	130.78 (15)	C13—C15—C16—C17	−177.90 (15)
C3—N1—C7—C12	−51.5 (2)	C20—C15—C16—C17	0.8 (2)
C3—N2—N3—C13	172.11 (13)	C13—C15—C20—C19	177.96 (14)
N3—N2—C3—S1	0.83 (17)	C16—C15—C20—C19	−0.7 (2)
N3—N2—C3—N1	−178.90 (12)	C15—C16—C17—C18	−0.3 (3)
N2—N3—C13—C14	1.6 (2)	C16—C17—C18—O4	179.96 (15)
N2—N3—C13—C15	−179.18 (12)	C16—C17—C18—C19	−0.3 (2)
O1—C1—C2—S1	−179.96 (13)	O4—C18—C19—C20	−179.92 (14)
O1—C1—C2—C4	0.6 (2)	C17—C18—C19—C20	0.4 (2)
N1—C1—C2—S1	−0.45 (15)	C18—C19—C20—C15	0.1 (2)
N1—C1—C2—C4	−179.95 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1i	0.84 (2)	1.96 (2)	2.7901 (16)	174.8 (19)
C8—H8···S1ii	0.95	2.82	3.7272 (17)	160
C10—H10···O4iii	0.95	2.52	3.452 (2)	167
C14—H14A···N2	0.98	2.30	2.742 (2)	106
C19—H19···O1i	0.95	2.47	3.200 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1i	0.84 (2)	1.96 (2)	2.7901 (16)	174.8 (19)
C8—H8⋯S1ii	0.95	2.82	3.7272 (17)	160
C10—H10⋯O4iii	0.95	2.52	3.452 (2)	167
C19—H19⋯O1i	0.95	2.47	3.200 (2)	133

Symmetry codes: (i) ; (ii) ; (iii) .