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Volume 69 
Part 9 
Pages o1408-o1409  
September 2013  

Received 6 August 2013
Accepted 7 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 16.3
Details
Open access

(4E)-4-[(2-Hydroxyanilino)methylidene]-1-phenylpyrazolidine-3,5-dione dimethyl sulfoxide hemisolvate

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,dDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada E-18071, Spain,eDepartment of Chemistry, Sohag University, 82524 Sohag, Egypt,fDepartment of Chemistry, University of Leicester, Leicester, England, and gKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The asymmetric unit of the title compound, C16H13N3O3·0.5C2H6OS, is composed of two independent pyrazolidine-3,5-dione molecules and one dimethyl sulfoxide solvent molecule. In each pyrazolidine-3,5-dione molecule, an intramolecular N-H...O hydrogen bond forms an S(5)S(6) motif. In the crystal, pairs of each independent pyrazolidine-3,5-dione molecule are linked by N-H...O hydrogen bonds, forming dimers with R22(8) motifs. These dimers are connected with the other molecules through the solvent molecules via O-H...O hydrogen bonds, forming ribbons along the b-axis direction. C-H...[pi] interactions connect the ribbons. C-H...O interactions also occur.

Related literature

For the significant role of pyrazolidinediones in the synthesis of various heterocyclic compounds, see: Elnagdy & Ohta (1973[Elnagdy, M. H. & Ohta, M. (1973). Bull. Chem. Soc. Jpn, 46, 1830-1833.]); Abdel-Rahman et al. (2004[Abdel-Rahman, M. A., Khodairy, A. A.-B. A. G., Ghattas, A.-B. A. G. & Younes, S. (2004). J. Chin. Chem. Soc. 51, 103-114.]); Khodairy (2007[Khodairy, M. A. (2007). J. Chin. Chem. Soc. 54, 93-102.]). For the diverse biological actvities of pyrazolidinedione-containing compounds, see: D'Alo et al. (1978[D'Alo, G., Conti, G., Gadel, S. & Dalla Vedova, R. (1978). Farm. Ed. Sci. 33, 106-116.]); Tawab et al. (1960[Tawab, S. A., Moustafa, A. & Kira, M. (1960). Nature, 186, 165-166.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13N3O3·0.5C2H6OS

  • Mr = 334.37

  • Triclinic, [P \overline 1]

  • a = 5.7740 (2) Å

  • b = 14.9402 (6) Å

  • c = 19.2441 (7) Å

  • [alpha] = 106.060 (1)°

  • [beta] = 93.459 (1)°

  • [gamma] = 92.653 (1)°

  • V = 1588.96 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 100 K

  • 0.47 × 0.14 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.990

  • 25749 measured reflections

  • 7370 independent reflections

  • 5874 reflections with I > 2[sigma](I)

  • Rint = 0.043

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

  • wR(F2) = 0.112

  • S = 1.02

  • 7370 reflections

  • 453 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg6 are the centroids of the C11-C16 and C27-C32 phenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...O3 0.86 (2) 2.15 (2) 2.8265 (17) 135 (2)
O1-H1A...O5 0.85 (2) 1.80 (2) 2.6479 (17) 174 (2)
N3-H3A...O2i 0.88 (2) 1.90 (2) 2.7740 (17) 174 (2)
N4-H4A...O6 0.88 (2) 2.11 (2) 2.8050 (18) 136 (2)
O4-H4B...O7ii 0.85 (2) 1.76 (2) 2.6061 (18) 172 (2)
N6-H6...O6iii 0.88 (2) 1.92 (2) 2.7831 (19) 169 (2)
C34-H34B...O3iv 0.98 2.43 3.403 (3) 175
C29-H29...Cg3v 0.95 2.64 3.548 (2) 160
C33-H33C...Cg6vi 0.98 2.74 3.690 (2) 163
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x-1, y+1, z; (v) x+1, y+1, z; (vi) x-1, y, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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.]); 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: HG5338 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzon, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

Abdel-Rahman, M. A., Khodairy, A. A.-B. A. G., Ghattas, A.-B. A. G. & Younes, S. (2004). J. Chin. Chem. Soc. 51, 103-114.  [ChemPort]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
D'Alo, G., Conti, G., Gadel, S. & Dalla Vedova, R. (1978). Farm. Ed. Sci. 33, 106-116.  [ChemPort]
Elnagdy, M. H. & Ohta, M. (1973). Bull. Chem. Soc. Jpn, 46, 1830-1833.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Khodairy, M. A. (2007). J. Chin. Chem. Soc. 54, 93-102.  [ChemPort]
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]
Tawab, S. A., Moustafa, A. & Kira, M. (1960). Nature, 186, 165-166.  [CrossRef] [PubMed] [ChemPort] [ISI]


Acta Cryst (2013). E69, o1408-o1409   [ doi:10.1107/S1600536813022034 ]

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