(2E)-N′-[(E)-2-Hy­droxy­benzyl­idene]-3-phenyl­prop-2-enohydrazide

Samir A Carvalho; Edson F da Silva; Carlos A M Fraga; Solange M S V Wardell; James L Wardell; Edward R T Tiekink

doi:10.1107/S1600536812028516

. 2012 Jun 30;68(Pt 7):o2253–o2254. doi: 10.1107/S1600536812028516

(2E)-N′-[(E)-2-Hydroxybenzylidene]-3-phenylprop-2-enohydrazide

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

PMCID: PMC3394040 PMID: 22798905

Abstract

In the non-planar title compound, C₁₆H₁₄N₂O₂, the dihedral angle between the phenyl rings is 16.67 (8)°. An E conformation is found for each of the imine [1.286 (2) Å] and ethylene [1.335 (2) Å] bonds. The amide O and H atoms are anti, and an intramolecular hydroxy O—H⋯N hydrogen bond is noted. The formation of N—H⋯O(hydroxy) hydrogen bonds in the crystal packing leads to helical chains along the b axis. Supramolecular layers in the ab plane are formed as the chains are linked by C—H⋯O interactions.

Related literature

For background to the biological activity of compounds with the N-acylhydrazone framework, (E)-cinnamoylhydrazone derivatives, and related structures, see: Carvalho et al. (2012a ▶). For the synthesis, see: Carvalho et al. (2012b ▶). For background to the data collection at the National Crystallographic Service, see: Coles & Gale (2012 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M _r = 266.29
Orthorhombic,
a = 24.2707 (17) Å
b = 5.1322 (2) Å
c = 10.5192 (4) Å
V = 1310.29 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.19 × 0.09 × 0.03 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2011 ▶) T _min = 0.878, T _max = 1.000
5871 measured reflections
1575 independent reflections
1504 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.075
S = 0.93
1575 reflections
181 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrystalClear (Rigaku, 2011 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028516/hb6860sup1.cif

e-68-o2253-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028516/hb6860Isup2.hkl

e-68-o2253-Isup2.hkl^{(76.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028516/hb6860Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.85 (2)	1.86 (2)	2.6080 (19)	147 (2)
N2—H2n⋯O1ⁱ	0.88 (1)	2.05 (1)	2.9070 (19)	165 (2)
C3—H3⋯O2ⁱⁱ	0.95	2.54	3.215 (2)	128
C7—H7⋯O2ⁱⁱ	0.95	2.47	3.174 (2)	131

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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). Structural studies are supported by the Ministry of Higher Education (Malaysia) through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

supplementary crystallographic information

Comment

Compounds related to the title (E)-cinnamoylhydrazone derivative, (I), are of interest owing to their biological activities (Carvalho et al., 2012a). For example, (I), exhibits considerable trypanocidal activity (Carvalho et al., 2012b). Herein, the crystal structure determination of (I) is described.

In (I), Fig. 1, there is a twist in the molecule as seen in the dihedral angle between the phenyl rings of 16.67 (8)°. The greatest deviation from a planar torsion angle is found for C9—C10—C11—C16 of 8.4 (3)°. There is an intramolecular hydroxy-O1···N2 hydrogen bond. The conformation about each of the imine [N1═C7 = 1.286 (2) Å] and ethylene [C9═C10 = 1.335 (2) Å] bonds is E. The amide-O and –H atoms are anti. The molecular structure of (I) resembles that of the unsubstituted compound (Carvalho et al., 2012a) where the dihedral angle between terminal phenyl rings is 25.48 (12)°.

The formation of N—H···O hydrogen bonds between the amide-H and hydroxyl-O leads to helical supramolecular chains along the b axis, Fig. 2 and Table 1. The chains are linked into a supramolecular layer in the ab plane by C—H···O interactions, Fig. 3 and Table 1; the layers inter-digitate along the c axis, Fig. 4.

Experimental

The title compound was prepared as reported (Carvalho et al., 2012b). The sample used in the crystallographic study was grown from its EtOH solution and intensity data was collected at the National Crystallographic Service, England (Coles & Gale, 2012).