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Volume 68 
Part 12 
Page o3380  
December 2012  

Received 6 September 2012
Accepted 30 October 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.042
wR = 0.116
Data-to-parameter ratio = 16.6
Details
Open access

4-{[2-(2,4-Dinitrophenyl)hydrazinylidene](phenyl)methyl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate

aUniversity of Fort Hare, Department of Chemistry, Private Bag X1314, Alice 5700, South Africa, and bNelson Mandela Metropolitan University, Department of Chemistry, PO Box 77000, Port Elizabeth 6031, South Africa
Correspondence e-mail: idemudiaog@yahoo.com

In the title compound, C23H18N6O5·C2H6O, all three benzene rings lie in an approximate plane [maximum deviation = 0.2688 (16) Å] that makes an angle of 53.56 (3)° with the plane of the pyrazolone ring. Intramolecular N-H...O hydrogen bonds occur. In the crystal, the ethanol solvent molecule links adjacent molecules through N-H...O-H...O hydrogen bonds, leading to an infinite chain along the c-axis direction. The ethyl group of the ethanol solvent molecule is disordered over two set of sites in a 0.762 (5):0.238 (5) ratio.

Related literature

For a related structure, see: Idemudia et al. (2012[Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1280-o1281.]).

[Scheme 1]

Experimental

Crystal data
  • C23H18N6O5·C2H6O

  • Mr = 504.50

  • Monoclinic, P 21 /c

  • a = 12.8289 (4) Å

  • b = 14.3247 (4) Å

  • c = 14.4213 (4) Å

  • [beta] = 111.347 (1)°

  • V = 2468.38 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.61 × 0.43 × 0.39 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.89, Tmax = 0.96

  • 23873 measured reflections

  • 6124 independent reflections

  • 5136 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.04

  • 6124 reflections

  • 368 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.28 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
N4-H4N...O1 0.915 (17) 2.023 (17) 2.8261 (13) 145.6 (14)
N4-H4N...O2 0.915 (17) 2.040 (17) 2.6497 (14) 122.8 (13)
N2-H2N...O6i 0.936 (18) 1.711 (18) 2.6464 (14) 177.4 (16)
O6-H6...O1 0.89 (2) 1.72 (2) 2.5863 (14) 167 (2)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. 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.]) and SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: NG5294 ).


Acknowledgements

The authors would like to thank the Department of Chemistry and Govan Mbeki Research and Development Centre (GMRDC) both of the University of Fort Hare for their support.

References

Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.  [ISI] [CrossRef] [details]
Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1280-o1281.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3380  [ doi:10.1107/S1600536812044935 ]

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