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Volume 66 
Part 9 
Pages o2410-o2411  
September 2010  

Received 31 July 2010
Accepted 23 August 2010
Online 28 August 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.007 Å
R = 0.084
wR = 0.196
Data-to-parameter ratio = 12.9
Details
Open access

(2E)-N'-[(E)-4-Chlorobenzylidene]-3-phenylprop-2-enohydrazide monohydrate

aFioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Farmanguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil,bPrograma de Pós-Graduação em Química, Instituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro, RJ, Brazil,cLaboratório de Avaliação e Síntese de Substâncias Bioativas, Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, PO Box 68023, 21941-902 Rio de Janeiro, RJ, Brazil,dCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland,eCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and fDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The conformation about each of the imine and ethene bonds in the title hydrazide hydrate, C16H13ClN2O·H2O, is E. The hydrazide molecule is approximately planar (r.m.s. deviation of the 20 non-H atoms = 0.172 Å). The most significant twist occurs about the ethene bond [C-C=C-C = 164.1 (5)°] and the dihedral angle formed between the benzene rings is 5.3 (2)°]. In the crystal, the presence of N-H...Ow and O-H...Oc (× 2; w = water and c = carbonyl) hydrogen bonds leads to a supramolecular array in the bc plane.

Related literature

For background to the resurgence of tuberculosis; see Bezerra et al. (2006[Bezerra, D. P., Castro, F. O., Alves, A. P. N. N., Pessoa, C., Moraes, M. O., Silveira, E. R., Lima, M. A. S., Elmiro, F. J. M. & Costa-Lotufo, L. V. (2006). Braz. J. Med. Biol. Res. 39, 801-807.]); Chung & Shin (2007[Chung, H. S. & Shin, J. C. (2007). Food Chem. 104, 1670-1677.]); Naz et al. (2006[Naz, S., Ahmad, S., Rasool, S. A., Sayeed, S. A. & Siddiqi, R. (2006). Microb. Res. 161, 43-48.]). For background to the biological activity of trans-cinnamic acid derivatives, see: Carvalho et al. (2008[Carvalho, S. R., da Silva, E. F., de Souza, M. V. N., Lourenco, M. C. S. & Vicente, F. R. (2008). Bioorg. Med. Chem. Lett. 18, 538-541.]). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008[Carvalho, S. R., da Silva, E. F., de Souza, M. V. N., Lourenco, M. C. S. & Vicente, F. R. (2008). Bioorg. Med. Chem. Lett. 18, 538-541.], 2009[Carvalho, S. A., da Silva, E. F., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2009). Acta Cryst. E65, o3118.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13ClN2O·H2O

  • Mr = 302.75

  • Monoclinic, P 21 /c

  • a = 34.078 (3) Å

  • b = 5.9824 (6) Å

  • c = 7.2912 (6) Å

  • [beta] = 95.674 (3)°

  • V = 1479.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 120 K

  • 0.10 × 0.08 × 0.03 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.492, Tmax = 1.000

  • 8532 measured reflections

  • 2572 independent reflections

  • 2016 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.084

  • wR(F2) = 0.196

  • S = 1.05

  • 2572 reflections

  • 199 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2n...O1w 0.86 (2) 1.97 (3) 2.811 (6) 165 (5)
O1w-H1w...O1i 0.84 (5) 2.05 (5) 2.877 (5) 166 (4)
O1w-H2w...O1ii 0.85 (4) 2.10 (4) 2.923 (5) 165 (5)
Symmetry codes: (i) x, y+1, z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: HB5594 ).


Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

Bezerra, D. P., Castro, F. O., Alves, A. P. N. N., Pessoa, C., Moraes, M. O., Silveira, E. R., Lima, M. A. S., Elmiro, F. J. M. & Costa-Lotufo, L. V. (2006). Braz. J. Med. Biol. Res. 39, 801-807.  [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Carvalho, S. R., da Silva, E. F., de Souza, M. V. N., Lourenco, M. C. S. & Vicente, F. R. (2008). Bioorg. Med. Chem. Lett. 18, 538-541.  [CrossRef] [PubMed] [ChemPort]
Carvalho, S. A., da Silva, E. F., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2009). Acta Cryst. E65, o3118.  [CSD] [CrossRef] [details]
Chung, H. S. & Shin, J. C. (2007). Food Chem. 104, 1670-1677.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Naz, S., Ahmad, S., Rasool, S. A., Sayeed, S. A. & Siddiqi, R. (2006). Microb. Res. 161, 43-48.  [CrossRef] [ChemPort]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2010). E66, o2410-o2411   [ doi:10.1107/S160053681003388X ]

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