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Volume 69 
Part 2 
Page o187  
February 2013  

Received 7 December 2012
Accepted 14 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.087
Data-to-parameter ratio = 12.6
Details
Open access
ADDENDA AND ERRATA

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(E)-3-Amino-4-(2-phenylhydrazinylidene)-1H-pyrazol-5(4H)-one

aChemistry Department, Faculty of Science, Helwan University, Cairo, Egypt, and bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, Germany
Correspondence e-mail: elgemeie@yahoo.com

The molecule of the title compound, C9H9N5O, is essentially planar (r.m.s. deviation of all atoms = 0.02 Å) except for the NH2 H atoms. An intramolecular hydrazinylidene-carbonyl N-H...O=C hydrogen bond is present. In the crystal, molecules are connected via N-H...N/O hydrogen bonds, forming thick layers parallel to (100).

Related literature

The synthesis, chemistry and biological/medical activity of related compounds is described in: Elgemeie (2003[Elgemeie, G. H. (2003). Curr. Pharm. Des. 9, 2627-2642.]); Elgemeie & El-Aziz (2002[Elgemeie, G. H. & El-Aziz, H. A. (2002). Synth. Commun. 32, 253-261.]); Elgemeie & Sood (2003[Elgemeie, G. H. & Sood, S. A. (2003). Synth. Commun. 33, 2095-2105.], 2006[Elgemeie, G. H. & Sood, S. A. (2006). Synth. Commun. 36, 743-753.]); Elgemeie et al. (2001[Elgemeie, G. H., El-Ezbawy, S. R. & El-Aziz, H. A. (2001). Synth. Commun. 31, 3453-3451.], 2007[Elgemeie, G. H., Elghandour, A. H. & Abd Elaziz, G. W. (2007). Synth. Commun. 37, 2827-2834.], 2008[Elgemeie, G. H., Zaghary, W. A., Amin, K. M. & Nasr, T. M. (2008). J. Carbohydr. Chem. 27, 345-355.], 2009[Elgemeie, G. H., Zaghary, W. A., Amin, K. A. & Nasr, T. M. (2009). J. Carbohydr. Chem. 28, 161-170.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9N5O

  • Mr = 203.21

  • Monoclinic, P 21 /c

  • a = 6.7380 (2) Å

  • b = 13.4310 (4) Å

  • c = 10.4563 (3) Å

  • [beta] = 103.094 (3)°

  • V = 921.67 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.86 mm-1

  • T = 100 K

  • 0.15 × 0.10 × 0.03 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.668, Tmax = 1.000

  • 26682 measured reflections

  • 1914 independent reflections

  • 1807 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.087

  • S = 1.05

  • 1914 reflections

  • 152 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H01...O1i 0.909 (16) 1.949 (16) 2.8521 (11) 172.0 (14)
N3-H03B...N2ii 0.934 (17) 2.424 (16) 3.2711 (12) 150.8 (13)
N3-H03A...O1iii 0.908 (16) 2.141 (15) 2.9635 (11) 150.2 (13)
N5-H05...O1 0.897 (16) 2.174 (16) 2.8575 (11) 132.5 (13)
Symmetry codes: (i) -x, -y+1, -z; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2105 ).


References

Elgemeie, G. H. (2003). Curr. Pharm. Des. 9, 2627-2642.  [ISI] [CrossRef] [PubMed] [ChemPort]
Elgemeie, G. H. & El-Aziz, H. A. (2002). Synth. Commun. 32, 253-261.  [ISI] [CrossRef] [ChemPort]
Elgemeie, G. H., El-Ezbawy, S. R. & El-Aziz, H. A. (2001). Synth. Commun. 31, 3453-3451.  [ISI] [CrossRef] [ChemPort]
Elgemeie, G. H., Elghandour, A. H. & Abd Elaziz, G. W. (2007). Synth. Commun. 37, 2827-2834.  [ISI] [CrossRef] [ChemPort]
Elgemeie, G. H. & Sood, S. A. (2003). Synth. Commun. 33, 2095-2105.  [ISI] [CrossRef] [ChemPort]
Elgemeie, G. H. & Sood, S. A. (2006). Synth. Commun. 36, 743-753.  [ISI] [CrossRef] [ChemPort]
Elgemeie, G. H., Zaghary, W. A., Amin, K. M. & Nasr, T. M. (2008). J. Carbohydr. Chem. 27, 345-355.  [ISI] [CrossRef] [ChemPort]
Elgemeie, G. H., Zaghary, W. A., Amin, K. A. & Nasr, T. M. (2009). J. Carbohydr. Chem. 28, 161-170.  [ISI] [CrossRef] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o187  [ doi:10.1107/S1600536812050854 ]

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