2-[(E)-Phen­yl(2-phenyl­hydrazin-1-yl­idene)meth­yl]phenol

R Alan Howie; James L Wardell; Solange M S V Wardell; Edward R T Tiekink

doi:10.1107/S1600536812005387

. 2012 Feb 24;68(Pt 3):o796–o797. doi: 10.1107/S1600536812005387

2-[(E)-Phenyl(2-phenylhydrazin-1-ylidene)methyl]phenol

R Alan Howie ^a, James L Wardell ^b,^‡, Solange M S V Wardell ^c, Edward R T Tiekink ^d,^*

PMCID: PMC3297864 PMID: 22412667

Abstract

In the title hydrazone derivative, C₁₉H₁₆N₂O, a twist is found between the hydroxyphenyl and N-bound phenyl rings [dihedral angle = 24.37 (7)°]. The C-bound phenyl ring is almost perpendicular to each of these planes [dihedral angles = 75.30 (7) and 86.00 (7)°, respectively]. The conformation about the imine bond [1.2935 (17) Å] is E. The hydroxy group forms an intramolecular hydrogen bond with the imine N atom. Zigzag chains along [001] mediated by N—H⋯O hydrogen bonds feature in the crystal packing.

Related literature

For background on the influence of substituents upon the supramolecular structures of hydrazones, see: Glidewell et al. (2004 ▶); Ferguson et al. (2005 ▶); Wardell et al. (2007 ▶); Baddeley, de Souza França et al. (2009 ▶); Baddeley, Howie et al. (2009 ▶); de Souza et al. (2010 ▶); Howie, da Silva Lima et al. (2010 ▶); Howie, de Souza et al. (2010 ▶); Nogueira et al. (2011 ▶); Howie et al. (2011 ▶).

Experimental

Crystal data

C₁₉H₁₆N₂O
M _r = 288.34
Monoclinic,
a = 9.6796 (3) Å
b = 15.3312 (5) Å
c = 10.3593 (2) Å
β = 108.149 (2)°
V = 1460.84 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.49 × 0.38 × 0.18 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.857, T _max = 0.985
16532 measured reflections
3337 independent reflections
2624 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.141
S = 1.06
3337 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005387/bt5814sup1.cif

e-68-0o796-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005387/bt5814Isup2.hkl

e-68-0o796-Isup2.hkl^{(160.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005387/bt5814Isup3.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 (1)	1.76 (1)	2.5678 (14)	157 (2)
N2—H2N⋯O1ⁱ	0.89 (2)	2.43 (2)	3.2517 (16)	155 (1)

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Symmetry code: (i) Inline graphic .

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). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

For some time, we have been interested in the influence of substituents upon the supramolecular structures of hydrazones, especially of those having potential biological activities. These include substituted phenylhydrazines with substituted benzaldehydes (Glidewell et al., 2004; Ferguson et al., 2005) and 2-hydroxyacetophenone (Baddeley, de Souza França et al., 2009). Hydrazones derived from substituted benzaldehydes and (pyrazinecarbonyl)hydrazine (Baddeley, Howie et al., 2009; Howie, da Silva Lima et al., 2010), 2-hydrazinyl-benzothiazole (Nogueira et al., 2011), 7-chloroquinoline-4-hydrazide (Howie, de Souza et al., 2010; de Souza et al., 2010) and 2-hydrazinylacyl-N-isonicotine (Wardell et al., 2007) have also been investigated along with L-serinyl derivatives, (S)-2-hydroxy-1-[N-(benzylidene)-hydrazinylcarbonyl]ethylcarbamate esters (Howie et al., 2011). In continuation of these studies, herein the crystal and molecular structure of (E)-2-hydroxybenzophenone phenylhydrazone (I) is described.

In (I), Fig. 1, the hydroxy-benzene and N-bound phenyl rings are twisted, forming a dihedral angle of 24.37 (7)°. These planes form dihedral angles of 75.30 (7) and 86.00 (7)°, respectively, with the C-bound phenyl ring indicating an almost perpendicular relationship. The hydroxy group forms an intramolecular hydrogen bond with the imine-N1 atom, Table 1. The configuration about the imine bond N1═C7 [1.2935 (17) Å] is E.

The most prominent feature of the crystal packing is the formation of zigzag chains along [001] generated by glide symmetry and mediated by N—H···O hydrogen bonds, Fig. 2 and Table 1. Chains pack in the crystal structure with no specific intermolecular interactions between them, Fig. 3.

Experimental

A solution of phenylhydrazine and 2-hydroxybenzophenone (1 mmol each) in ethanol (20 ml) was refluxed for 1 h, rotary evaporated and the residue recrystallized from ethanol. IR (KBr, cm^-1): ν 3302, 1600, 1557. Analysis found: C 78.78, H 5.81, N 9.47%; calculated for C₁₉H₁₆N₂O: C 79.14, H 5.59, N 9.71%.