4-({(Z)-5-[(Z)-3-Eth­oxy-4-hy­droxy­benzyl­idene]-3-methyl-4-oxo-1,3-thia­zolidin-2-yl­idene}amino)­benzoic acid dimethyl­formamide monosolvate

Kosma, P.; Selzer, E.; Mereiter, K.

doi:10.1107/S1600536812047307

Volume 68
Part 12
Pages o3417-o3418
December 2012

Received 12 November 2012
Accepted 17 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.033
wR = 0.094
Data-to-parameter ratio = 21.5
Details

4-({(Z)-5-[(Z)-3-Ethoxy-4-hydroxybenzylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene}amino)benzoic acid dimethylformamide monosolvate

Paul Kosma,^a Edgar Selzer ^b and Kurt Mereiter ^c ^*

^aDepartment of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria,^bUniversity Clinic of Radiotherapy, Medical University Vienna, Währinger Gürtel 18-20, A-1090 Vienna, Austria, and ^cInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria
Correspondence e-mail: kurt.mereiter@tuwien.ac.at

The molecular structure of the title compound, C₂₀H₁₈N₂O₅S·C₃H₇NO, represents an essentially planar 5-benzylidene-thiazolidine moiety (r.m.s. deviation from planarity without ring substituents = 0.095 Å) to which the 4-aminobenzoic acid fragment is inclined at 76.23 (1)°. In the crystal, the benzoic acid molecules are arranged in layers parallel to [001] which are built up from inversion dimers held together by head-to-tail phenol-carboxy O-HO hydrogen bonds and head-to-tail [pi] - [pi] stacking interactions between the 5-benzylidene-thiazolidine moieties (ring centroid distance = 3.579 Å). These layers are separated by the dimethylformamide solvent molecules which are firmly anchored via a short O-HO hydrogen bond [OO = 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 [alpha] _v [beta] ₃ 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); Tomasciková et al. (2008).

Experimental

Crystal data

C₂₀H₁₈N₂O₅S·C₃H₇NO
M_r = 471.52
Triclinic, $[P \overline 1]$
a = 7.7532 (3) Å
b = 9.3081 (3) Å
c = 15.6969 (3) Å
= 86.390 (2)°
= 89.813 (2)°
= 87.656 (2)°
V = 1129.61 (6) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.094
S = 1.02
6537 reflections
304 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O5-H5oO6	0.84	1.73	2.5529 (10)	167
O3-H3oO4ⁱ	0.84	2.05	2.7386 (11)	139
Symmetry code: (i) -x, -y+2, -z+1.

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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2066 ).

Acknowledgements

The X-ray centre of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer.

References

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