(2E)-N′-Benzoyl-3-(4-nitro­phen­yl)prop-2-enohydrazide

Carvalho, S.A.; Silva, E.F. da; Souza, M.V.N. de; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809053379

Volume 66
Part 1
Pages o150-o151
January 2010

Received 9 December 2009
Accepted 11 December 2009
Online 16 December 2009

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.127
Data-to-parameter ratio = 14.8
Details

(2E)-N'-Benzoyl-3-(4-nitrophenyl)prop-2-enohydrazide

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

^aInstituto de Química, Universidade Federal do Rio de Janeiro, 21949-900 Rio de Janeiro, RJ, Brazil,^bDepartamento de Síntese Orgánica, Instituto de Tecnologia em Fármacos FIOCRUZ, Manguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil,^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia,^dCentro 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 ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C₁₆H₁₃N₃O₄, the dihedral angle between the terminal benzene rings is 14.02 (7)°. The carbonyl groups are anti with respect to each other, which facilitates their participation in the formation of supramolecular chains. Each side of the -C(=O)N(H)N(H)C(=O)- residue associates with a centrosymmetrically related molecule, resulting in the formation of essentially flat ten-membered {O=CNN(H)}₂ synthons. The resultant chains are further consolidated in the crystal structure via C-HO contacts.

Related literature

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

Experimental

Crystal data

C₁₆H₁₃N₃O₄
M_r = 311.29
Triclinic, $[P \overline 1]$
a = 6.8263 (2) Å
b = 9.6483 (3) Å
c = 10.8571 (3) Å
= 95.535 (2)°
= 102.701 (2)°
= 91.728 (2)°
V = 693.35 (4) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 120 K
0.50 × 0.40 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.664, T_max = 0.746
15199 measured reflections
3157 independent reflections
2495 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.127
S = 1.06
3157 reflections
214 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2nO4	0.88 (1)	2.27 (1)	2.6470 (16)	106 (1)
N2-H2nO4ⁱ	0.88 (1)	2.05 (1)	2.8721 (15)	155 (1)
N3-H3nO3	0.88 (1)	2.35 (1)	2.6687 (15)	101 (1)
N3-H3nO3ⁱⁱ	0.88 (1)	2.07 (1)	2.9269 (15)	165 (1)
C12-H12O4ⁱⁱⁱ	0.95	2.56	3.4257 (18)	151
C14-H14O1^iv	0.95	2.58	3.2851 (19)	132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x+2, y, z-1.

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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5278 ).

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., Lourenço, 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. (2009). publCIF. In preparation.

organic compounds