(E)-N′-(3-Hy­droxy-4-meth­oxy­benzyl­idene)-4-meth­oxy­benzohydrazide

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

doi:10.1107/S1600536811048240

. 2011 Nov 19;67(Pt 12):o3370–o3371. doi: 10.1107/S1600536811048240

(E)-N′-(3-Hydroxy-4-methoxybenzylidene)-4-methoxybenzohydrazide

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

PMCID: PMC3239014 PMID: 22199863

Abstract

The title molecule, a benzohydrazide derivative, C₁₆H₁₆N₂O₄, is twisted with a dihedral angle of 69.97 (5)° between the two benzene rings. An intramolecular O—H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, molecules are linked by N—H⋯O and weak C—H⋯O hydrogen bonds into a chain along the c axis. C—H⋯π interactions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For details of 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 of benzohydrazide derivatives, see: Bedia et al. (2006 ▶); Loncle et al. (2004 ▶); Melnyk et al. (2006 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M _r = 300.31
Monoclinic,
a = 12.1323 (19) Å
b = 12.9727 (15) Å
c = 9.6714 (12) Å
β = 113.213 (2)°
V = 1398.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.58 × 0.30 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.942, T _max = 0.993
14521 measured reflections
3704 independent reflections
3260 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.109
S = 1.03
3704 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.23 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/S1600536811048240/is5009sup1.cif

e-67-o3370-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048240/is5009Isup2.hkl

e-67-o3370-Isup2.hkl^{(181.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811048240/is5009Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O4	0.87 (2)	2.18 (2)	2.6692 (13)	115.9 (18)
N1—H1N1⋯O1ⁱ	0.887 (18)	1.992 (18)	2.8698 (13)	170.0 (16)
C8—H8A⋯O1ⁱ	0.93	2.47	3.2780 (15)	145
C15—H15C⋯Cg1ⁱⁱ	0.96	2.72	3.5664 (15)	148
C16—H16B⋯Cg1ⁱⁱⁱ	0.96	2.76	3.4366 (16)	128

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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. The authors also thank the Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Benzohydrazide derivatives have been reported to possess various biological properties, such as antibacterial and antifungal (Loncle et al., 2004), antitubercular (Bedia et al., 2006), antimalarial (Melnyk et al., 2006) and antiproliferative (Raj et al., 2007) activities. We have previously reported some crystal structures of this type of compounds (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). The title compound (I) was synthesized in order to study the effect of functional groups to their bioactivities comparing to the closely related structures. (I) was screened for antibacterial and antioxidant activities. Our results show that (I) exhibits moderate antibacterial activity whereas it is inactive for antioxidant activity. The three dimensional structure of (I) was studied in order to gain more details to explain the effect of structure on its bioactivity.

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₆H₁₆N₂O₄, exists in a trans-configuration with respect to the C8═N2 bond [1.2808 (14) Å] and the torsion angle of N1–N2–C8–C9 is 179.20 (9)°. The molecule is twisted as indicated by the dihedral angle between the two benzene rings being 69.97 (5)°. The middle bridge fragment (O1/C7/N1/N2/C8) is nearly planar with a torsion angle N2–N1–C7–O1 = -0.80 (16)°. The mean plane through this bridge makes dihedral angles of 27.88 (7) and 43.44 (7)° with the C1–C6 and C9–C14 benzene rings, respectively. The methoxy group of 4-methoxyphenyl (at atom C4) is co-planar with its bound benzene ring [torsion angle C15–O2–C4–C5 = -0.76 (16)° and r.m.s 0.0131 (1) Å for the seven non H atoms], whereas the methoxy group of the 3-hydroxy-4-methoxyphenyl (at atom C12) is slight deviated with a torsion angle C16–O4–C12–C13 = 10.02 (15)°. An intramolecular O3—H1O3···O4 hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995). Bond distances are of normal values (Allen et al., 1987) and are comparable with the 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 hydrogen bonds and weak C—H···O interactions (Table 1) into chains along the c axis. These chains are arranged in a face-to-face manner. The crystal is stabilized by N—H···O hydrogen bonds, weak C—H···O and C—H···π interactions (Table 1).

Experimental

The title compound (I) was prepared by dissolving 4-methoxybenzohydrazide (2 mmol, 0.33 g) in ethanol (10 ml). The solution of 3-hydroxy-4-methoxybenzaldehyde (2 mmol, 0.30 g) in ethanol (10 ml) was then added slowly to the reaction. The mixture was refluxed for around 3 hr. The solution was then cooled to room temperature. Colorless plate-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. 491-492 K).