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Volume 68 
Part 5 
Page o1299  
May 2012  

Received 8 March 2012
Accepted 30 March 2012
Online 4 April 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.081
Data-to-parameter ratio = 13.5
Details
Open access

N'-Cyclopentylidenepyridine-4-carbohydrazide

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, PO Wits 2050, South Africa,bFaculty of Science, NYU Abu Dhabi, PO Box 129188, Abu Dhabi, United Arab Emirates, and cInstitute of Mineralogy and Petrography, University of Innsbruck, Innsbruck 6020, Austria
Correspondence e-mail: andreas.lemmerer@wits.ac.za

The title compound, C11H13N3O, is a derivative of the antituberculosis drug isoniazid [systematic name: pyridine-4-carbohydrazide]. The crystal structure consists of repeating hydrogen-bonded chains parallel to the b axis. Adjacent molecules in the chains are linked by bifurcated N-H...(O,N) hydrogen bonds, which form an R12(5) ring motif.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13N3O

  • Mr = 203.24

  • Orthorhombic, P b c a

  • a = 15.762 (3) Å

  • b = 8.1144 (16) Å

  • c = 16.015 (3) Å

  • V = 2048.3 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.35 × 0.22 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Gemini R diffractometer

  • Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.970, Tmax = 0.983

  • 11794 measured reflections

  • 1884 independent reflections

  • 1420 reflections with I > 2[sigma](I)

  • Rint = 0.034

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

  • wR(F2) = 0.081

  • S = 0.96

  • 1884 reflections

  • 140 parameters

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

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N3i 0.889 (15) 2.303 (15) 3.1155 (16) 151.9 (12)
N1-H1...O1i 0.889 (15) 2.607 (15) 3.3368 (14) 140.0 (11)
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CrysAlis PRO (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) 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: FY2050 ).


Acknowledgements

This work was supported in part by grant No. 2004118 from the United States-Israel Binational Science Foundation (Jerusalem). AL thanks the South African National Research Foundation for a postdoctoral scholarship (SFP2007070400002), the Oppenheimer Memorial Trust for financial support and the Molecular Sciences Institute for infrastructure.

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o1299  [ doi:10.1107/S1600536812013815 ]

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