4-({(Z)-5-[(Z)-3-Eth-oxy-4-hy-droxy-benzyl-idene]-3-methyl-4-oxo-1,3-thia-zolidin-2-yl-idene}amino)-benzoic acid dimethyl-formamide monosolvate.

The mol-ecular structure of the title compound, C20H18N2O5S·C3H7NO, represents an essentially planar 5-benzyl-idene-thia-zolidine moiety (r.m.s. deviation from planarity without ring substituents = 0.095 Å) to which the 4-amino-benzoic acid fragment is inclined at 76.23 (1)°. In the crystal, the benzoic acid mol-ecules are arranged in layers parallel to [001] which are built up from inversion dimers held together by head-to-tail phenol-carb-oxy O-H⋯O hydrogen bonds and head-to-tail π-π stacking inter-actions between the 5-benzyl-idene-thia-zolidine moieties (ring centroid distance = 3.579 Å). These layers are separated by the dimethyl-formamide solvent mol-ecules which are firmly anchored via a short O-H⋯O hydrogen bond [O⋯O = 2.5529 (10) Å] donated by the -COOH group.

Related literature

For bioactive compounds based on the 4-thia­zolidinone scaffold of the title compound, see: Ottanà et al. (2005 ▶); Verma & Saraf (2008 ▶). For potential anti­cancer activity via αvβ3 integrin antagonistic properties of 4-thia­zolidinone derivatives, see: Dayam et al. (2006 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For crystal structures related to that of the title compound, see: Ottanà et al. (2005 ▶); Yavari et al. (2008 ▶); Deepthi et al. (2001 ▶); Tomaščiková et al. (2008 ▶).

Experimental

Crystal data

C20H18N2O5S·C3H7NO

M = 471.52

Triclinic,

a = 7.7532 (3) Å

b = 9.3081 (3) Å

c = 15.6969 (3) Å

α = 86.390 (2)°

β = 89.813 (2)°

γ = 87.656 (2)°

V = 1129.61 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.53 × 0.35 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.89, T max = 0.96

29040 measured reflections

6537 independent reflections

5993 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.02

6537 reflections

304 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047307/fk2066sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047307/fk2066Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047307/fk2066Isup3.cml

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

C20H18N2O5S·C3H7NO	Z = 2
Mr = 471.52	F(000) = 496
Triclinic, P1	Dx = 1.386 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7532 (3) Å	Cell parameters from 9007 reflections
b = 9.3081 (3) Å	θ = 2.2–30.0°
c = 15.6969 (3) Å	µ = 0.19 mm−1
α = 86.390 (2)°	T = 100 K
β = 89.813 (2)°	Prism, yellow
γ = 87.656 (2)°	0.53 × 0.35 × 0.24 mm
V = 1129.61 (6) Å3

Bruker Kappa APEXII CCD diffractometer	6537 independent reflections
Radiation source: fine-focus sealed tube	5993 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.89, Tmax = 0.96	k = −13→13
29040 measured reflections	l = −22→22

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.4019P] where P = (Fo2 + 2Fc2)/3
6537 reflections	(Δ/σ)max = 0.002
304 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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	0.41930 (3)	0.65538 (2)	0.349946 (14)	0.01698 (6)
O1	0.80606 (9)	0.38102 (8)	0.35244 (5)	0.02040 (14)
O2	0.37560 (9)	0.96319 (8)	0.62843 (5)	0.02005 (14)
O3	0.65049 (10)	0.96754 (8)	0.73138 (5)	0.02233 (15)
H3o	0.5526	1.0091	0.7342	0.033*
O4	−0.39179 (10)	0.90766 (9)	0.17578 (5)	0.02725 (17)
O5	−0.23650 (9)	1.02278 (8)	0.07406 (5)	0.02368 (16)
H5o	−0.3306	1.0689	0.0647	0.036*
N1	0.57050 (10)	0.44691 (8)	0.26982 (5)	0.01658 (15)
N2	0.33188 (11)	0.54753 (9)	0.19732 (5)	0.01936 (16)
C1	0.43011 (12)	0.54409 (10)	0.26183 (6)	0.01595 (16)
C2	0.60871 (14)	0.34431 (11)	0.20524 (7)	0.02270 (19)
H2A	0.7153	0.2885	0.2205	0.034*
H2B	0.6232	0.3965	0.1496	0.034*
H2C	0.5133	0.2789	0.2022	0.034*
C3	0.67482 (12)	0.45592 (10)	0.33963 (6)	0.01610 (16)
C4	0.60700 (12)	0.56946 (10)	0.39437 (6)	0.01610 (16)
C5	0.69539 (12)	0.59362 (10)	0.46550 (6)	0.01749 (17)
H5	0.7951	0.5316	0.4740	0.021*
C6	0.67052 (12)	0.69420 (10)	0.53172 (6)	0.01676 (17)
C7	0.52167 (12)	0.78354 (10)	0.54232 (6)	0.01713 (17)
H7	0.4277	0.7816	0.5037	0.021*
C8	0.51260 (12)	0.87446 (10)	0.60936 (6)	0.01695 (17)
C9	0.65368 (12)	0.87976 (10)	0.66581 (6)	0.01783 (17)
C10	0.79983 (13)	0.79211 (11)	0.65505 (6)	0.01950 (18)
H10	0.8948	0.7954	0.6929	0.023*
C11	0.80769 (12)	0.69964 (10)	0.58921 (6)	0.01877 (18)
H11	0.9078	0.6389	0.5829	0.023*
C12	0.22371 (12)	0.96318 (10)	0.57563 (6)	0.01843 (17)
H12A	0.1783	0.8652	0.5764	0.022*
H12B	0.2514	0.9948	0.5159	0.022*
C13	0.09223 (13)	1.06669 (11)	0.61232 (7)	0.02253 (19)
H13A	0.0657	1.0338	0.6713	0.034*
H13B	−0.0134	1.0705	0.5780	0.034*
H13C	0.1392	1.1629	0.6115	0.034*
C14	0.18954 (12)	0.64677 (10)	0.18805 (6)	0.01736 (17)
C15	0.03664 (13)	0.62483 (11)	0.23377 (6)	0.02102 (19)
H15	0.0308	0.5477	0.2762	0.025*
C16	−0.10619 (13)	0.71632 (11)	0.21680 (6)	0.02002 (18)
H16	−0.2100	0.7017	0.2479	0.024*
C17	−0.09940 (12)	0.82963 (10)	0.15451 (6)	0.01648 (17)
C18	0.05412 (12)	0.85138 (10)	0.10947 (6)	0.01830 (17)
H18	0.0599	0.9289	0.0673	0.022*
C19	0.19814 (12)	0.76057 (11)	0.12589 (6)	0.01939 (18)
H19	0.3021	0.7757	0.0950	0.023*
C20	−0.25683 (12)	0.92308 (11)	0.13672 (6)	0.01868 (18)
O6	−0.49662 (10)	1.18732 (8)	0.02984 (5)	0.02426 (16)
N3	−0.76655 (11)	1.27974 (10)	0.05269 (6)	0.02176 (17)
C21	−0.63956 (13)	1.18080 (11)	0.06532 (6)	0.02044 (18)
H21	−0.6593	1.1002	0.1038	0.025*
C22	−0.74498 (16)	1.40627 (12)	−0.00518 (7)	0.0282 (2)
H22A	−0.7384	1.4918	0.0279	0.042*
H22B	−0.8436	1.4184	−0.0442	0.042*
H22C	−0.6384	1.3938	−0.0381	0.042*
C23	−0.92669 (15)	1.27171 (13)	0.10088 (8)	0.0296 (2)
H23A	−0.9239	1.1831	0.1381	0.044*
H23B	−1.0242	1.2713	0.0613	0.044*
H23C	−0.9399	1.3553	0.1357	0.044*

	U11	U22	U33	U12	U13	U23
S1	0.01676 (11)	0.01661 (11)	0.01742 (11)	0.00188 (8)	−0.00169 (8)	−0.00148 (8)
O1	0.0160 (3)	0.0205 (3)	0.0241 (3)	0.0017 (2)	−0.0018 (3)	0.0007 (3)
O2	0.0156 (3)	0.0244 (3)	0.0204 (3)	0.0021 (3)	−0.0045 (2)	−0.0046 (3)
O3	0.0187 (3)	0.0284 (4)	0.0204 (3)	0.0015 (3)	−0.0037 (3)	−0.0071 (3)
O4	0.0177 (3)	0.0369 (4)	0.0265 (4)	0.0031 (3)	0.0047 (3)	−0.0001 (3)
O5	0.0171 (3)	0.0238 (4)	0.0289 (4)	0.0042 (3)	0.0005 (3)	0.0049 (3)
N1	0.0170 (4)	0.0158 (3)	0.0168 (3)	0.0017 (3)	−0.0013 (3)	−0.0016 (3)
N2	0.0195 (4)	0.0195 (4)	0.0187 (4)	0.0026 (3)	−0.0031 (3)	−0.0005 (3)
C1	0.0158 (4)	0.0148 (4)	0.0170 (4)	−0.0002 (3)	0.0000 (3)	0.0007 (3)
C2	0.0264 (5)	0.0214 (4)	0.0203 (4)	0.0046 (4)	−0.0009 (4)	−0.0053 (3)
C3	0.0157 (4)	0.0153 (4)	0.0172 (4)	−0.0025 (3)	−0.0001 (3)	0.0013 (3)
C4	0.0151 (4)	0.0154 (4)	0.0176 (4)	−0.0013 (3)	−0.0001 (3)	0.0006 (3)
C5	0.0160 (4)	0.0176 (4)	0.0187 (4)	−0.0014 (3)	−0.0006 (3)	0.0007 (3)
C6	0.0158 (4)	0.0176 (4)	0.0168 (4)	−0.0021 (3)	−0.0013 (3)	0.0009 (3)
C7	0.0150 (4)	0.0191 (4)	0.0172 (4)	−0.0024 (3)	−0.0030 (3)	0.0011 (3)
C8	0.0147 (4)	0.0184 (4)	0.0175 (4)	−0.0018 (3)	−0.0012 (3)	0.0011 (3)
C9	0.0168 (4)	0.0206 (4)	0.0162 (4)	−0.0030 (3)	−0.0015 (3)	−0.0001 (3)
C10	0.0159 (4)	0.0241 (4)	0.0184 (4)	−0.0011 (3)	−0.0040 (3)	−0.0005 (3)
C11	0.0156 (4)	0.0211 (4)	0.0194 (4)	0.0000 (3)	−0.0025 (3)	0.0003 (3)
C12	0.0155 (4)	0.0204 (4)	0.0194 (4)	−0.0010 (3)	−0.0038 (3)	−0.0007 (3)
C13	0.0184 (4)	0.0230 (5)	0.0262 (5)	0.0011 (3)	−0.0025 (4)	−0.0029 (4)
C14	0.0176 (4)	0.0187 (4)	0.0158 (4)	0.0010 (3)	−0.0037 (3)	−0.0021 (3)
C15	0.0227 (5)	0.0222 (4)	0.0175 (4)	0.0000 (3)	0.0003 (3)	0.0032 (3)
C16	0.0185 (4)	0.0234 (4)	0.0180 (4)	−0.0016 (3)	0.0024 (3)	0.0006 (3)
C17	0.0148 (4)	0.0189 (4)	0.0158 (4)	−0.0003 (3)	−0.0004 (3)	−0.0023 (3)
C18	0.0163 (4)	0.0189 (4)	0.0193 (4)	−0.0002 (3)	0.0006 (3)	0.0019 (3)
C19	0.0157 (4)	0.0210 (4)	0.0210 (4)	0.0001 (3)	0.0012 (3)	0.0017 (3)
C20	0.0163 (4)	0.0214 (4)	0.0186 (4)	0.0002 (3)	−0.0007 (3)	−0.0040 (3)
O6	0.0219 (4)	0.0275 (4)	0.0226 (3)	0.0059 (3)	−0.0010 (3)	0.0004 (3)
N3	0.0206 (4)	0.0220 (4)	0.0226 (4)	0.0031 (3)	−0.0031 (3)	−0.0029 (3)
C21	0.0223 (5)	0.0210 (4)	0.0180 (4)	0.0021 (3)	−0.0045 (3)	−0.0018 (3)
C22	0.0351 (6)	0.0217 (5)	0.0268 (5)	0.0067 (4)	−0.0057 (4)	0.0010 (4)
C23	0.0212 (5)	0.0342 (6)	0.0344 (6)	0.0010 (4)	0.0011 (4)	−0.0103 (5)

S1—C4	1.7564 (10)	C11—H11	0.9500
S1—C1	1.7793 (9)	C12—C13	1.5116 (14)
O1—C3	1.2197 (12)	C12—H12A	0.9900
O2—C8	1.3628 (11)	C12—H12B	0.9900
O2—C12	1.4423 (11)	C13—H13A	0.9800
O3—C9	1.3533 (12)	C13—H13B	0.9800
O3—H3o	0.8400	C13—H13C	0.9800
O4—C20	1.2200 (12)	C14—C19	1.3978 (13)
O5—C20	1.3227 (12)	C14—C15	1.3993 (13)
O5—H5o	0.8400	C15—C16	1.3852 (14)
N1—C3	1.3729 (12)	C15—H15	0.9500
N1—C1	1.3873 (12)	C16—C17	1.3948 (13)
N1—C2	1.4575 (12)	C16—H16	0.9500
N2—C1	1.2671 (12)	C17—C18	1.3978 (13)
N2—C14	1.4118 (12)	C17—C20	1.4863 (13)
C2—H2A	0.9800	C18—C19	1.3874 (13)
C2—H2B	0.9800	C18—H18	0.9500
C2—H2C	0.9800	C19—H19	0.9500
C3—C4	1.4824 (13)	O6—C21	1.2406 (13)
C4—C5	1.3475 (13)	N3—C21	1.3270 (13)
C5—C6	1.4494 (13)	N3—C23	1.4539 (14)
C5—H5	0.9500	N3—C22	1.4563 (14)
C6—C11	1.4015 (13)	C21—H21	0.9500
C6—C7	1.4103 (13)	C22—H22A	0.9800
C7—C8	1.3912 (13)	C22—H22B	0.9800
C7—H7	0.9500	C22—H22C	0.9800
C8—C9	1.4143 (13)	C23—H23A	0.9800
C9—C10	1.3851 (14)	C23—H23B	0.9800
C10—C11	1.3857 (14)	C23—H23C	0.9800
C10—H10	0.9500
C4—S1—C1	91.11 (4)	C13—C12—H12B	110.4
C8—O2—C12	117.96 (7)	H12A—C12—H12B	108.6
C9—O3—H3o	109.5	C12—C13—H13A	109.5
C20—O5—H5o	109.5	C12—C13—H13B	109.5
C3—N1—C1	116.78 (8)	H13A—C13—H13B	109.5
C3—N1—C2	121.81 (8)	C12—C13—H13C	109.5
C1—N1—C2	121.36 (8)	H13A—C13—H13C	109.5
C1—N2—C14	121.40 (8)	H13B—C13—H13C	109.5
N2—C1—N1	120.85 (8)	C19—C14—C15	120.18 (9)
N2—C1—S1	128.47 (7)	C19—C14—N2	118.40 (9)
N1—C1—S1	110.67 (7)	C15—C14—N2	121.13 (9)
N1—C2—H2A	109.5	C16—C15—C14	119.55 (9)
N1—C2—H2B	109.5	C16—C15—H15	120.2
H2A—C2—H2B	109.5	C14—C15—H15	120.2
N1—C2—H2C	109.5	C15—C16—C17	120.75 (9)
H2A—C2—H2C	109.5	C15—C16—H16	119.6
H2B—C2—H2C	109.5	C17—C16—H16	119.6
O1—C3—N1	123.42 (9)	C16—C17—C18	119.36 (9)
O1—C3—C4	125.97 (9)	C16—C17—C20	119.06 (8)
N1—C3—C4	110.60 (8)	C18—C17—C20	121.57 (8)
C5—C4—C3	118.33 (8)	C19—C18—C17	120.46 (9)
C5—C4—S1	130.83 (8)	C19—C18—H18	119.8
C3—C4—S1	110.81 (7)	C17—C18—H18	119.8
C4—C5—C6	133.55 (9)	C18—C19—C14	119.69 (9)
C4—C5—H5	113.2	C18—C19—H19	120.2
C6—C5—H5	113.2	C14—C19—H19	120.2
C11—C6—C7	118.94 (9)	O4—C20—O5	123.61 (9)
C11—C6—C5	115.68 (8)	O4—C20—C17	122.94 (9)
C7—C6—C5	125.38 (8)	O5—C20—C17	113.45 (8)
C8—C7—C6	119.89 (9)	C21—N3—C23	121.33 (9)
C8—C7—H7	120.1	C21—N3—C22	120.97 (9)
C6—C7—H7	120.1	C23—N3—C22	117.53 (9)
O2—C8—C7	126.07 (9)	O6—C21—N3	123.87 (10)
O2—C8—C9	113.74 (8)	O6—C21—H21	118.1
C7—C8—C9	120.18 (9)	N3—C21—H21	118.1
O3—C9—C10	118.26 (9)	N3—C22—H22A	109.5
O3—C9—C8	121.99 (9)	N3—C22—H22B	109.5
C10—C9—C8	119.74 (9)	H22A—C22—H22B	109.5
C9—C10—C11	120.09 (9)	N3—C22—H22C	109.5
C9—C10—H10	120.0	H22A—C22—H22C	109.5
C11—C10—H10	120.0	H22B—C22—H22C	109.5
C10—C11—C6	121.14 (9)	N3—C23—H23A	109.5
C10—C11—H11	119.4	N3—C23—H23B	109.5
C6—C11—H11	119.4	H23A—C23—H23B	109.5
O2—C12—C13	106.71 (8)	N3—C23—H23C	109.5
O2—C12—H12A	110.4	H23A—C23—H23C	109.5
C13—C12—H12A	110.4	H23B—C23—H23C	109.5
O2—C12—H12B	110.4
C14—N2—C1—N1	−179.41 (8)	O2—C8—C9—O3	−0.99 (13)
C14—N2—C1—S1	−1.09 (14)	C7—C8—C9—O3	179.48 (9)
C3—N1—C1—N2	176.75 (9)	O2—C8—C9—C10	178.36 (9)
C2—N1—C1—N2	−0.86 (14)	C7—C8—C9—C10	−1.18 (14)
C3—N1—C1—S1	−1.85 (10)	O3—C9—C10—C11	179.38 (9)
C2—N1—C1—S1	−179.46 (7)	C8—C9—C10—C11	0.01 (14)
C4—S1—C1—N2	−177.56 (9)	C9—C10—C11—C6	0.98 (15)
C4—S1—C1—N1	0.90 (7)	C7—C6—C11—C10	−0.81 (14)
C1—N1—C3—O1	−176.93 (8)	C5—C6—C11—C10	179.63 (9)
C2—N1—C3—O1	0.67 (14)	C8—O2—C12—C13	178.41 (8)
C1—N1—C3—C4	1.95 (11)	C1—N2—C14—C19	108.96 (11)
C2—N1—C3—C4	179.54 (8)	C1—N2—C14—C15	−77.22 (13)
O1—C3—C4—C5	−0.48 (14)	C19—C14—C15—C16	0.23 (15)
N1—C3—C4—C5	−179.32 (8)	N2—C14—C15—C16	−173.49 (9)
O1—C3—C4—S1	177.69 (8)	C14—C15—C16—C17	0.20 (15)
N1—C3—C4—S1	−1.15 (9)	C15—C16—C17—C18	−0.59 (15)
C1—S1—C4—C5	178.01 (10)	C15—C16—C17—C20	178.47 (9)
C1—S1—C4—C3	0.14 (7)	C16—C17—C18—C19	0.56 (14)
C3—C4—C5—C6	178.92 (9)	C20—C17—C18—C19	−178.48 (9)
S1—C4—C5—C6	1.18 (17)	C17—C18—C19—C14	−0.13 (15)
C4—C5—C6—C11	−170.63 (10)	C15—C14—C19—C18	−0.27 (15)
C4—C5—C6—C7	9.84 (17)	N2—C14—C19—C18	173.62 (9)
C11—C6—C7—C8	−0.36 (13)	C16—C17—C20—O4	1.91 (15)
C5—C6—C7—C8	179.15 (9)	C18—C17—C20—O4	−179.04 (10)
C12—O2—C8—C7	0.83 (14)	C16—C17—C20—O5	−177.34 (9)
C12—O2—C8—C9	−178.67 (8)	C18—C17—C20—O5	1.71 (13)
C6—C7—C8—O2	−178.13 (9)	C23—N3—C21—O6	−175.35 (10)
C6—C7—C8—C9	1.34 (14)	C22—N3—C21—O6	−0.22 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5o···O6	0.84	1.73	2.5529 (10)	167
O3—H3o···O4i	0.84	2.05	2.7386 (11)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5o⋯O6	0.84	1.73	2.5529 (10)	167
O3—H3o⋯O4i	0.84	2.05	2.7386 (11)	139

Symmetry code: (i) .