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Volume 69 
Part 12 
Pages o1844-o1845  
December 2013  

Received 22 November 2013
Accepted 24 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.070
wR = 0.156
Data-to-parameter ratio = 10.8
Details
Open access

Dimethyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-meth­oxy-2-oxo­ethyl­idene)-4-oxo-3-phenyl-1,3-thia­zolidin-2-yl­idene]hydra­zin-1-yl­idene}eth­yl)anilino]but-2-ene­dio­ate

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The mol­ecule of the title compound, C26H24N4O7S, adopts a trans conformation about the central N-N bond, presumably to minimize steric between the substituents on these two atoms. An intra­molecular N-H...O hydrogen bond occurs. The phenyl ring is disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8). The azolidine ring is essentially planar [maximum deviation = 0.008 (5) Å] and makes a dihedral angle of 4.3 (2)° with the benzene ring and dihedral angles of 74.1 (3) and 69.1 (5)°, respectively, with the mean planes of the major and minor components of the disordered phenyl ring. The packing in the crystal is aided by the formation of several weak C-H...O and C-H...N inter­actions.

Related literature

For the biological activity of thia­zolidinene-containing compounds, see: Chaudhari et al. (1975[Chaudhari, S. K., Verma, M., Chaturvedi, A. K. & Parmar, S. S. (1975). J. Pharm. Sci. 64, 614-617.]); Chaudhary et al. (1976[Chaudhary, M., Parmar, S. S., Chaudhary, S. K., Chaturvedi, A. K. & Rama, S. B. V. (1976). J. Pharm. Sci. 65, 443-446.]); Babaoglu et al. (2003[Babaoglu, K., Page, M. A., Jones, V. C., McNeil, M. R., Dong, C., Naismith, J. H. & Lee, R. E. (2003). Bioorg. Med. Chem. Lett. 13, 3227-3230.]); Dwivedi et al. (1972[Dwivedi, C., Gupta, T. K. & Parmar, S. S. (1972). J. Med. Chem. 15, 553-554.]); Parmar et al. (1972[Parmar, S. S., Dwivedi, C., Chaudhari, A. & Gupta, T. K. (1972). J. Med. Chem. 15, 99-101.]); Bondock et al. (2007[Bondock, S., Khalifa, W. & Fadda, A. A. (2007). Eur. J. Med. Chem. 42, 948-954.]); Vicini et al. (2008[Vicini, P., Geronikaki, A., Incerti, M., Zani, F., Dearden, J. & Hewitt, M. (2008). Bioorg. Med. Chem. 16, 3714-3724.]); Gududuru et al. (2004[Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. Chem. Lett. 14, 5289-5293.]); Ottanà et al. (2005[Ottanà, R., Carotti, S., Maccari, R., Landini, I., Chiricosta, G., Caciagli, B. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 3930-3933.]); Agrawal et al. (2000[Agrawal, V. K., Sachan, S. & Khadikar, P. V. (2000). Acta Pharm. 50, 281-290.]); Diurno et al. (1999[Diurno, M. V., Mazzoni, O., Correale, G., Monterrey, I. G., Calignano, A., La Rana, G. & Bolognese, A. (1999). II Farmaco, 54, 579-583.]); Omar et al. (2010[Omar, K., Geronikaki, A., Zoumpoulakis, P., Camoutsis, C., Sokovic, M., Ciric, A. & Glamoclija, J. (2010). Bioorg. Med. Chem. 18, 426-432.]); Vigorita et al. (2003[Vigorita, M. G., Ottanà, R., Monforte, F., Maccari, R., Monforte, M. T., Trovato, A., Taviano, M. F., Miceli, N., De Luca, G., Alcaro, S. & Ortuso, F. (2003). Bioorg. Med. Chem. 11, 999-1006.]); Rawal et al. (2005[Rawal, R. K., Prabhakar, Y. S., Katti, S. B. & De Clercq, E. (2005). Bioorg. Med. Chem. 13, 6771-6776.]); Suzuki et al. (1999[Suzuki, Y., Akima, M. & Tamura, K. (1999). Gen. Pharmacol. 32, 57-63.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24N4O7S

  • Mr = 536.56

  • Monoclinic, P 21 /n

  • a = 15.7027 (6) Å

  • b = 4.8543 (2) Å

  • c = 33.5974 (13) Å

  • [beta] = 92.539 (3)°

  • V = 2558.47 (17) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.59 mm-1

  • T = 100 K

  • 0.16 × 0.03 × 0.03 mm

Data collection
  • Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.83, Tmax = 0.95

  • 11600 measured reflections

  • 3655 independent reflections

  • 2351 reflections with I > 2[sigma](I)

  • Rint = 0.106

  • [theta]max = 59.1°

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.156

  • S = 1.03

  • 3655 reflections

  • 339 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...O6 0.88 2.01 2.705 (5) 135
C1-H1B...O4i 0.98 2.54 3.402 (8) 147
C3-H3...O3ii 0.95 2.37 3.191 (6) 145
C8B-H8B...N2iii 0.95 2.58 3.461 (8) 155
C12B-H12B...O3iv 0.95 2.31 3.216 (7) 159
C14-H14A...O6v 0.98 2.50 3.375 (6) 148
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+3, -z; (iii) x, y+1, z; (iv) x, y-1, z; (v) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5373 ).


Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

References

Agrawal, V. K., Sachan, S. & Khadikar, P. V. (2000). Acta Pharm. 50, 281-290.  [ChemPort]
Babaoglu, K., Page, M. A., Jones, V. C., McNeil, M. R., Dong, C., Naismith, J. H. & Lee, R. E. (2003). Bioorg. Med. Chem. Lett. 13, 3227-3230.  [CrossRef] [PubMed] [ChemPort]
Bondock, S., Khalifa, W. & Fadda, A. A. (2007). Eur. J. Med. Chem. 42, 948-954.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chaudhari, S. K., Verma, M., Chaturvedi, A. K. & Parmar, S. S. (1975). J. Pharm. Sci. 64, 614-617.  [CrossRef] [PubMed] [ChemPort]
Chaudhary, M., Parmar, S. S., Chaudhary, S. K., Chaturvedi, A. K. & Rama, S. B. V. (1976). J. Pharm. Sci. 65, 443-446.  [CrossRef] [PubMed] [ChemPort]
Diurno, M. V., Mazzoni, O., Correale, G., Monterrey, I. G., Calignano, A., La Rana, G. & Bolognese, A. (1999). II Farmaco, 54, 579-583.  [CrossRef] [ChemPort]
Dwivedi, C., Gupta, T. K. & Parmar, S. S. (1972). J. Med. Chem. 15, 553-554.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. Chem. Lett. 14, 5289-5293.  [CrossRef] [PubMed] [ChemPort]
Omar, K., Geronikaki, A., Zoumpoulakis, P., Camoutsis, C., Sokovic, M., Ciric, A. & Glamoclija, J. (2010). Bioorg. Med. Chem. 18, 426-432.  [CrossRef] [PubMed] [ChemPort]
Ottanà, R., Carotti, S., Maccari, R., Landini, I., Chiricosta, G., Caciagli, B. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 3930-3933.  [PubMed]
Parmar, S. S., Dwivedi, C., Chaudhari, A. & Gupta, T. K. (1972). J. Med. Chem. 15, 99-101.  [CrossRef] [ChemPort] [PubMed]
Rawal, R. K., Prabhakar, Y. S., Katti, S. B. & De Clercq, E. (2005). Bioorg. Med. Chem. 13, 6771-6776.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suzuki, Y., Akima, M. & Tamura, K. (1999). Gen. Pharmacol. 32, 57-63.  [CrossRef] [ChemPort] [PubMed]
Vicini, P., Geronikaki, A., Incerti, M., Zani, F., Dearden, J. & Hewitt, M. (2008). Bioorg. Med. Chem. 16, 3714-3724.  [CrossRef] [PubMed] [ChemPort]
Vigorita, M. G., Ottanà, R., Monforte, F., Maccari, R., Monforte, M. T., Trovato, A., Taviano, M. F., Miceli, N., De Luca, G., Alcaro, S. & Ortuso, F. (2003). Bioorg. Med. Chem. 11, 999-1006.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1844-o1845   [ doi:10.1107/S1600536813032042 ]

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