(E)-N′-(3-Eth­oxy-4-hy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

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

doi:10.1107/S1600536812007374

. 2012 Feb 24;68(Pt 3):o849–o850. doi: 10.1107/S1600536812007374

(E)-N′-(3-Ethoxy-4-hydroxybenzylidene)-4-methoxybenzohydrazide

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

PMCID: PMC3297905 PMID: 22412708

Abstract

In the molecule of the title benzohydrazide derivative, C₁₇H₁₈N₂O₄, the dihedral angle between the benzene rings is 6.86 (11)°. The methoxy group of the 4-methoxyphenyl fragment deviates slightly [C_methyl—O—C—C = 10.0 (4)°] with respect to the benzene ring, whereas the ethoxy group of the 3-ethoxy-4-hydroxyphenyl fragment is is almost coplanar [C—O—C—C_methyl = 178.5 (2)°]. In the crystal, molecules are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network parallel to the ab plane. C—H⋯π interactions and C⋯O [2.980 (3) Å] short contacts are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Promdet et al. (2011 ▶). For background and applications to benzohydrazide derivatives, see: Bedia et al. (2006 ▶); Loncle et al. (2004 ▶); Raj et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₄
M _r = 314.33
Orthorhombic,
a = 5.0607 (9) Å
b = 11.086 (2) Å
c = 27.629 (5) Å
V = 1550.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 297 K
0.56 × 0.10 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.948, T _max = 0.993
10252 measured reflections
2637 independent reflections
1921 reflections with I > 2σ(I)
R _int = 0.100

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.154
S = 1.04
2637 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536812007374/rz2713sup1.cif

e-68-0o849-sup1.cif^{(25.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007374/rz2713Isup2.hkl

e-68-0o849-Isup2.hkl^{(129.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812007374/rz2713Isup3.cml

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

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

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3	0.82	2.41	2.683 (2)	100
O4—H1O4⋯O1ⁱ	0.82	2.21	2.981 (2)	156
N1—H1N1⋯O1ⁱⁱ	0.90	2.10	2.994 (3)	172
C10—H10A⋯O4ⁱⁱⁱ	0.93	2.55	3.462 (3)	168
C16—H16B⋯Cg1ⁱ	0.97	2.68	3.499 (2)	142

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

Acknowledgments

PP thanks the Development and Promotion of Science and Technology Talents Project for a fellowship. JH thanks the Crystal Materials Research Unit, Prince of Songkla University, for financial support. PP and JH thank Dr Nawong Boonnak for useful suggestions. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for baterial assays. The authors thank the Prince of Songkla University and the Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

During the course of our on-going research on benzohydrazide derivatives, which have been reported to possess various biological properties such as antibacterial and antifungal (Loncle et al., 2004), antitubercular (Bedia et al., 2006) and antiproliferative (Raj et al., 2007) activities, the synthesis and crystal structures of benzohydrazide derivatives have been reported (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). The title compound was synthesized and tested for its antioxidant and antibacterial activities and found to be inactive.

The molecule of the title benzohydrazide derivative (Fig. 1) exists in a trans-configuration with respect to the C8═N2 bond [1.286 (4) Å], as indicated by the torsion angle N1–N2–C8–C9 = -178.2 (2)°. The molecule is slightly twisted with the dihedral angle between the two benzene rings of 6.86 (11)°. The middle bridge fragment (O1/C7/N1/N2/C8) is planar with the torsion angle N2–N1–C7–O1 = 0.8 (4)° and the r.m.s. of 0.0360 (2) Å for the five non-H atoms. The mean plane through this bridge makes dihedral angles of 28.94 (15) and 26.51 (15)° with the C1–C6 and C9–C14 phenyl rings, respectively. The methoxy group of 4-methoxyphenyl is slightly twisted with respect to its bound benzene ring [torsion angle C15–O2–C4–C5 = 10.0 (4)°], whereas the ethoxy group of 3-ethoxy-4-hydroxyphenyl is co-planar with the torsion angle C11–O3–C16–C17 = 178.5 (2)°.

An intramolecular O4—H1O4···O3 hydrogen bond generates a S(5) ring motif (Bernstein et al., 1995). Bond distances are of normal values (Allen et al., 1987) and are comparable with those found in related structures (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O and O—H···O hydrogen bonds and weak C—H···O interactions (Table 1) into a two-dimensional network paralell to the ab plane. The crystal is further stabilized by C—H···π weak interaction (Table 1). A C8···O4^iv [2.980 (3) Å: (iv) = -x, 1/2+y, 1/2+z] short contact was observed.

Experimental

The title compound was prepared by dissolving 4-methoxybenzohydrazide (2 mmol, 0.30 g) in ethanol (10 ml). A solution of 3-ethoxy-4-hydroxybenzaldehyde (2 mmol, 0.30 g) in ethanol (10 ml) was then added slowly to the reaction. The mixture was refluxed for about 5 h and a white solid appeared. The mixture was then cooled to room temperature and filtered. Colourless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after several days. M. p. 486-488 K.