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

Carvalho, S.A.; Silva, E.F. da; Fraga, C.A.M.; Wardell, S.M.S.V.; Wardell, J.L.; Tiekink, E.R.T.

doi:10.1107/S160053681003388X

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 (C-C) = 0.007 Å
R = 0.084
wR = 0.196
Data-to-parameter ratio = 12.9
Details

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

Samir A. Carvalho,^a,^b Edson F. da Silva,^a Carlos A. M. Fraga,^b,^c Solange M. S. V. Wardell,^d James L. Wardell ^e ⁺ and Edward R. T. Tiekink ^f ^*

^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-HO_w and O-HO_c (× 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); Chung & Shin (2007); Naz et al. (2006). For background to the biological activity of trans-cinnamic acid derivatives, see: Carvalho et al. (2008). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008, 2009).

Experimental

Crystal data

C₁₆H₁₃ClN₂O·H₂O
M_r = 302.75
Monoclinic, P 2₁ /c
a = 34.078 (3) Å
b = 5.9824 (6) Å
c = 7.2912 (6) Å
= 95.674 (3)°
V = 1479.2 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.492, T_max = 1.000
8532 measured reflections
2572 independent reflections
2016 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(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
_max = 0.36 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2nO1w	0.86 (2)	1.97 (3)	2.811 (6)	165 (5)
O1w-H1wO1ⁱ	0.84 (5)	2.05 (5)	2.877 (5)	166 (4)
O1w-H2wO1ⁱⁱ	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); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
Carvalho, S. A., da Silva, E. F., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2009). Acta Cryst. E65, o3118.
Chung, H. S. & Shin, J. C. (2007). Food Chem. 104, 1670-1677.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds