(E)-N′-(4-Eth­oxy­benzyl­idene)-4-hy­droxy­benzohydrazide dihydrate

Hoong-Kun Fun; Jirapa Horkaew; Suchada Chantrapromma; Chatchanok Karalai

doi:10.1107/S1600536812019356

. 2012 May 5;68(Pt 6):o1655–o1656. doi: 10.1107/S1600536812019356

(E)-N′-(4-Ethoxybenzylidene)-4-hydroxybenzohydrazide dihydrate

Hoong-Kun Fun ^a,^*,^‡, Jirapa Horkaew ^b, Suchada Chantrapromma ^b,^§, Chatchanok Karalai ^b

PMCID: PMC3379254 PMID: 22719452

Abstract

The benzohydrazide molecule of the title compound, C₁₆H₁₆N₂O₃·2H₂O, exists in a trans conformation with respect to the C=N double bond. The central O=C—NH—N=C plane [r.m.s. deviation of 0.0165 (1) Å for the five non-H atoms] makes dihedral angles of 6.04 (8) and 2.38 (8)°, respectively, with the hydroxy- and ethoxy-substituted benzene rings. The dihedral angle between these benzene rings is 3.82 (7)°. The ethoxy group is almost coplanar with the attached benzene ring with a C—O—C—C torsion angle of −176.58 (11)°. In the crystal, the benzohydrazide and water molecules are linked by N—H⋯O, O—H⋯O , O—H⋯N and C—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶, 2012 ▶). For applications of benzohydrazides, see: Loncle et al. (2004 ▶); Molyneux (2004 ▶); Promdet et al. (2011 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-68-o1655-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O₃·2H₂O
M _r = 320.34
Monoclinic,
a = 7.1655 (1) Å
b = 17.3895 (3) Å
c = 13.6202 (2) Å
β = 110.875 (1)°
V = 1585.74 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.29 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.971, T _max = 0.984
22228 measured reflections
5737 independent reflections
4310 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.155
S = 1.03
5737 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019356/is5130sup1.cif

e-68-o1655-sup1.cif^{(26KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019356/is5130Isup2.hkl

e-68-o1655-Isup2.hkl^{(280.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019356/is5130Isup3.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
O2—H1⋯O1ⁱ	0.84	1.77	2.6106 (15)	174
N1—H2⋯O1Wⁱⁱ	0.85	2.10	2.9278 (16)	167
O1W—H3⋯O2ⁱⁱⁱ	0.81	2.06	2.8683 (15)	177
O1W—H4⋯O2W	0.88	1.84	2.7159 (19)	169
O2W—H5⋯O1^iv	0.87	2.14	2.8558 (18)	139
O2W—H5⋯N2^iv	0.87	2.55	3.3363 (19)	151
O2W—H6⋯O3^v	0.89	2.11	2.9791 (17)	165
C6—H6A⋯O1Wⁱⁱ	0.95	2.36	3.2942 (18)	169
C8—H8A⋯O1Wⁱⁱ	0.95	2.49	3.3222 (18)	146

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

Acknowledgments

JH thanks the Graduate School, Prince of Songkla University, for partial financial support. The authors thank Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

It has been known that a majority of benzohydrazides possesses various biological properties, such as antibacterial and antifungal (Loncle et al., 2004), and antiproliferative (Raj et al., 2007) activities. The title benzohydrazide derivative (I) was synthesized as part of our study on the bioactivity of benzohydrazide derivatives (Fun et al., 2011; Horkaew et al., 2011, 2012; Promdet et al., 2011) and was evaluated for antioxidant activity by DPPH scavenging (Molyneux, 2004). It was found to be active. Herein we report the synthesis and crystal structure of (I).

The title compound (Fig. 1), C₁₆H₁₆N₂O₃.2H₂O, comprises one benzohydrazide molecule and two water molecules. The molecule of benzohydrazide exists in a trans-configuration with respect to the C8═N2 bond and the torsion angle N1—N2—C8—C9 = -179.90 (11)° with the dihedral angle between the two benzene rings being 3.82 (7)°. The middle fragment are planar with an r.m.s. deviation of 0.0165 (1) Å for the five non-H atoms (O1, C7, N1, N2 and C8). The mean plane through this middle fragment makes the dihedral angles of 6.04 (8) and 2.38 (8)° with the 4-hydroxyphenyl and 4-ethoxyphenyl rings, respectively. The ethoxy group is co-planar with the bound benzene ring with the torsion angle C12—O3—C15—C16 = -176.58 (11)°. The molecule is therefore approximately planar. The two water molecules are linked to each other by an O—H···O hydrogen bond (Fig. 1). Bond distances of benzohydrazide are of normal values (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Horkaew et al., 2011, 2012).

In the crystal packing (Fig. 2), the molecules of benzohydrazide and water are linked by N—H···O, O—H···O, O—H···N and C—H···O hydrogen bonds (Table 1) into a three-dimensional network.

Experimental

The title compound (I) was prepared by dissolving 4-hydroxybenzohydrazide (2 mmol, 0.30 g) in ethanol (15 ml). A solution of 4-ethoxybenzaldehyde (2 mmol, 0.27 ml) in ethanol (15 ml) was then added slowly to the reaction. The mixture was refluxed for around 6 hr. The solution was then cooled to room temperature and a white solid appeared. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from a methanol solution by slow evaporation of the solvent at room temperature after several days (m.p. 373-374 K).