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Volume 69 
Part 9 
Pages o1401-o1402  
September 2013  

Received 19 July 2013
Accepted 1 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 19.3
Details
Open access

Methyl (2Z)-((2Z)-2-{(2E)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)ethanoate

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

The asymmetric unit of the title compound, C21H19N3O3S, contains two independent molecules. In one molecule, the 1,3-thiazolidine ring forms dihedral angles of 86.19 (8) and 8.37 (8)° with the phenyl and benzene rings, respectively. The corresponding dihedral angles in the other molecule are 69.60 (7) and 14.08 (7)°. The dihedral angle between the phenyl and benzene rings is 84.70 (8)° in one molecule and 69.62 (8)° in the other. In the crystal, molecules pack in layers approximately parallel to (10-2). There are weak C-H...O hydrogen bonds within these layers. Further weak C-H...O hydrogen bonding occurs between the layers to form a three-dimensional network. A weak C-H...[pi] interaction is also observed.

Related literature

For the synthesis and general applications of thiazolidines, see: Pandey et al. (2011[Pandey, Y., Sharma, P. K., Kumar, N. & Singh, A. (2011). Int. J. Pharm. Tech. Res. 3, 980-985.]); Barreca et al. (2002[Barreca, M. L., Balzarini, J., Chimirri, A., Clercq, E. D., Luca, L. D., Höltje, H. D., Höltje, M., Monforte, A. M., Monforte, P., Pannecouque, C., Rao, A. & Zappala, M. (2002). J. Med. Chem. 45, 5410-5413.]); Botti et al. (1996[Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018-10024.]); Pfahl et al. (2003[Pfahl, M., Al-Shamma, H. A., Fanjul, A. N., Pleynet, D. P. M., Bao, H., Spruce, L. W., Cow, C. N., Tachdjian, C., Zapt, J. W. & &Wiemann, T. R. (2003). Patent WO 2003/050 098; Int. Appl. No. PCT/US2002/039 178.]); Sayyed et al. (2006[Sayyed, M., Mokle, S., Bokhare, M., Mankar, A., Surwase, S., Bhusare, S. & Vilohute, Y. (2006). Arkivoc, ii, 187-197.]); Sharma et al. (2006[Sharma, R., Nagda, D. P. & Talesara, G. L. (2006). Arkivoc, i, 1-12.]); 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.]); Çapan et al. (1999[Çapan, G., Ulusoy, N., Ergenç, N. & Kiraz, M. (1999). Monatsh. Chem. 130, 1399-1407.]). For standard bond-length data, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19N3O3S

  • Mr = 393.46

  • Monoclinic, P 21 /c

  • a = 8.3713 (12) Å

  • b = 21.568 (3) Å

  • c = 21.591 (3) Å

  • [beta] = 96.411 (2)°

  • V = 3873.9 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 150 K

  • 0.19 × 0.19 × 0.11 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.81, Tmax = 0.98

  • 69242 measured reflections

  • 9850 independent reflections

  • 7890 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.112

  • S = 1.05

  • 9850 reflections

  • 511 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C36-C41 ring.

D-H...A D-H H...A D...A D-H...A
C4-H4...O6i 0.95 2.56 3.4802 (19) 163
C6-H6B...O4i 0.98 2.52 3.465 (2) 163
C8-H8...O2ii 0.95 2.56 3.359 (2) 142
C12-H12...O4 0.95 2.43 3.302 (2) 152
C27-H27B...O1i 0.98 2.45 3.410 (2) 166
C30-H30...O5iii 0.95 2.44 3.331 (2) 157
C32-H32...O1iv 0.95 2.57 3.340 (2) 139
C33-H33...Cgv 0.95 2.58 3.4951 (19) 162
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) -x+1, -y, -z.

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: 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).; 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: LH5636 ).


Acknowledgements

The use of X-ray crystallographic facilities at Tulane University, USA, is gratefully acknowledged, We thank Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

References

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.
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.  [PubMed]
Barreca, M. L., Balzarini, J., Chimirri, A., Clercq, E. D., Luca, L. D., Höltje, H. D., Höltje, M., Monforte, A. M., Monforte, P., Pannecouque, C., Rao, A. & Zappala, M. (2002). J. Med. Chem. 45, 5410-5413.  [ISI] [CrossRef] [PubMed] [ChemPort]
Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018-10024.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Çapan, G., Ulusoy, N., Ergenç, N. & Kiraz, M. (1999). Monatsh. Chem. 130, 1399-1407.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Pandey, Y., Sharma, P. K., Kumar, N. & Singh, A. (2011). Int. J. Pharm. Tech. Res. 3, 980-985.  [ChemPort]
Pfahl, M., Al-Shamma, H. A., Fanjul, A. N., Pleynet, D. P. M., Bao, H., Spruce, L. W., Cow, C. N., Tachdjian, C., Zapt, J. W. & &Wiemann, T. R. (2003). Patent WO 2003/050 098; Int. Appl. No. PCT/US2002/039 178.
Sayyed, M., Mokle, S., Bokhare, M., Mankar, A., Surwase, S., Bhusare, S. & Vilohute, Y. (2006). Arkivoc, ii, 187-197.  [CrossRef]
Sharma, R., Nagda, D. P. & Talesara, G. L. (2006). Arkivoc, i, 1-12.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1401-o1402   [ doi:10.1107/S1600536813021533 ]

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