(2E)-N′-[(E)-Benzyl­idene]-3-phenyl­prop-2-enohydrazide from synchrotron radiation

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/S1600536812028504

. 2012 Jun 30;68(Pt 7):o2255–o2256. doi: 10.1107/S1600536812028504

(2E)-N′-[(E)-Benzylidene]-3-phenylprop-2-enohydrazide from synchrotron radiation

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: PMC3394041 PMID: 22798906

Abstract

In the title compound, C₁₆H₁₄N₂O, the dihedral angle between the phenyl rings is 25.48 (12)°. An E conformation is found for each of the imine [1.269 (3) Å] and ethylene [1.313 (3) Å] bonds. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, leading to zigzag chains along [010]. Supramolecular layers in the ab plane are formed, whereby the chains are linked by C—H⋯N and C—H⋯π interactions.

Related literature

For the biological activity of (E)-cinnamoylhydrazone derivatives against Chagas’ disease, see: Carvalho et al. (2012b ▶). For background to Chagas’ disease, see: Rassi et al. (2010 ▶); Soeiro & de Castro (2011 ▶). For related structural studies, see: Carvalho et al. (2009 ▶, 2010a ▶,b ▶, 2012a ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O
M _r = 250.30
Orthorhombic,
a = 11.473 (19) Å
b = 7.507 (13) Å
c = 30.50 (5) Å
V = 2627 (8) Å³
Z = 8
Synchrotron radiation
λ = 0.6943 Å
μ = 0.04 mm⁻¹
T = 120 K
0.12 × 0.03 × 0.02 mm

Data collection

Bruker SMART APEXII CCD diffractometer
14542 measured reflections
1876 independent reflections
1442 reflections with I > 2σ(I)
R _int = 0.084
θ_max = 22.7°

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.140
S = 1.05
1876 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028504/hb6861sup1.cif

e-68-o2255-sup1.cif^{(18KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028504/hb6861Isup2.hkl

e-68-o2255-Isup2.hkl^{(90.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028504/hb6861Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1ⁱ	0.88 (2)	1.93 (2)	2.816 (6)	175 (2)
C5—H5⋯N1ⁱⁱ	0.95	2.57	3.433 (7)	151
C3—H3⋯Cg1ⁱⁱⁱ	0.95	2.92	3.618 (7)	131
C6—H6⋯Cg1^iv	0.95	2.75	3.645 (7)	158

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

Acknowledgments

This work was supported by grants from CAPES, CNPq, FAPERJ and FIOCRUZ (Brazil). We thank Professor W. Clegg and the synchrotron component, based at Daresbury, of the EPSRC National Crystallographic Service, University of Southampton, for the data collection. Structural studies are supported by the Ministry of Higher Education (Malaysia) through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

(E)-Cinnamoylhydrazone derivatives have recently been shown to be agents against Chagas' disease (CD) (Carvalho et al., 2012b), caused by the parasite Trypanosoma cruzi. CD is the major cause of infectious cardiopathy and represents an important public health problem. It affects approximately eight million people in Latin America (Rassi et al., 2010). Neither the two established drugs, Nifurtimox and Benznidazole, is ideal because they present variable results depending on the phase of the disease, the dose and duration of the treatment, the patient's age and endemic region, as well as showing undesirable secondary side-effects (Soeiro & de Castro, 2011). The ArCH═ CHCONHN═CHAr' compounds used in the trypanocidal study (Carvalho et al., 2012b) indicated considerable biological potential. Following on from our structural studies on (E)-PhCH═CH-CONHNHPh (Carvalho et al., 2009), (E)-4-O₂NC₆H₄CH═CH-CONHNHCOPh (Carvalho et al., 2010a) and (E)-PhCH═CH-CONHN═ CHC₆H₄Cl-4.monohydrate (Carvalho et al., 2010b), we now wish to report the crystal structure of one of the compounds from the trypanocidal study, namely the title compound, (I).

In (I), Fig. 1, there is a twist in the molecule as seen in the dihedral angle between the phenyl rings of 25.48 (12)°. The greatest deviation from a planar torsion angle is found for C2—C1—C7—N1 of 14.0 (3)°. The conformation about each of the imine [N1═C7 = 1.269 (3) Å] and ethylene [C9═C10 = 1.313 (3) Å] bonds is E. In the structure of the 4-chlorobenzylidene derivative (Carvalho et al., 2010b), a decidedly more planar arrangement was noted (r.m.s. deviation of the 20 non-H atoms = 0.172 Å). However, a more twisted arrangement was found in the 2-hydroxyl derivative (Carvalho et al., 2012a) where the dihedral angle between the benzene rings is 16.67 (8)°.

In the crystal of (I), the molecules are linked by N—H···O hydrogen bonds (Table 1), resulting in zigzag chains along the b axis. The chains are linked into a supramolecular layer in the ab plane by C—H···N and C—H···π 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 in the form of small colourless needles.