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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 [sigma](C-C) = 0.001 Å
R = 0.033
wR = 0.094
Data-to-parameter ratio = 21.5
Details
Open access

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

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-H...O 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-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[Ottanà, R., Maccari, R., Barreca, M. L., Bruno, G., Rotondo, A., Rossi, A., Chiricosta, G., Di Paola, R., Sautebin, L., Cuzzocrea, S. & Vigorita, M. G. (2005). Bioorg. Med. Chem. 13, 4243-4252.]); Verma & Saraf (2008[Verma, A. & Saraf, S. K. (2008). Eur. J. Med. Chem. 43, 897-905.]). For potential anticancer activity via [alpha]v[beta]3 integrin antagonistic properties of 4-thiazolidinone derivatives, see: Dayam et al. (2006[Dayam, R., Aiello, F., Deng, J., Wu, Y., Garofalo, A., Chen, X. & Neamati, N. (2006). J. Med. Chem. 49, 4526-4534.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For crystal structures related to that of the title compound, see: Ottanà et al. (2005[Ottanà, R., Maccari, R., Barreca, M. L., Bruno, G., Rotondo, A., Rossi, A., Chiricosta, G., Di Paola, R., Sautebin, L., Cuzzocrea, S. & Vigorita, M. G. (2005). Bioorg. Med. Chem. 13, 4243-4252.]); Yavari et al. (2008[Yavari, I., Hosseini, N. & Moradi, L. (2008). Monatsh. Chem. 139, 133-136.]); Deepthi et al. (2001[Deepthi, S., Rajalakshmi, K., Gunasekaran, K., Velmurugan, D. & Nagarajan, K. (2001). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 369, 221-242.]); Tomasciková et al. (2008[Tomasciková, J., Danihel, I., Böhm, S., Imrich, J., Kristian, P., Potocnák, I., Cejka, J. & Klika, K. D. (2008). J. Mol. Struct. 875, 419-426.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O5S·C3H7NO

  • Mr = 471.52

  • Triclinic, [P \overline 1]

  • a = 7.7532 (3) Å

  • b = 9.3081 (3) Å

  • c = 15.6969 (3) Å

  • [alpha] = 86.390 (2)°

  • [beta] = 89.813 (2)°

  • [gamma] = 87.656 (2)°

  • V = 1129.61 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.89, Tmax = 0.96

  • 29040 measured reflections

  • 6537 independent reflections

  • 5993 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.094

  • S = 1.02

  • 6537 reflections

  • 304 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

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) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dayam, R., Aiello, F., Deng, J., Wu, Y., Garofalo, A., Chen, X. & Neamati, N. (2006). J. Med. Chem. 49, 4526-4534.  [ISI] [CrossRef] [PubMed] [ChemPort]
Deepthi, S., Rajalakshmi, K., Gunasekaran, K., Velmurugan, D. & Nagarajan, K. (2001). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 369, 221-242.  [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Ottanà, R., Maccari, R., Barreca, M. L., Bruno, G., Rotondo, A., Rossi, A., Chiricosta, G., Di Paola, R., Sautebin, L., Cuzzocrea, S. & Vigorita, M. G. (2005). Bioorg. Med. Chem. 13, 4243-4252.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tomasciková, J., Danihel, I., Böhm, S., Imrich, J., Kristian, P., Potocnák, I., Cejka, J. & Klika, K. D. (2008). J. Mol. Struct. 875, 419-426.
Verma, A. & Saraf, S. K. (2008). Eur. J. Med. Chem. 43, 897-905.  [ISI] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yavari, I., Hosseini, N. & Moradi, L. (2008). Monatsh. Chem. 139, 133-136.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3417-o3418   [ doi:10.1107/S1600536812047307 ]

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