(E)-4-Hy­droxy-N′-(3-hy­droxy-4-meth­oxy­benzyl­idene)benzohydrazide

Hoong-Kun Fun; Jirapa Horkaew; Suchada Chantrapromma

doi:10.1107/S1600536811036579

. 2011 Sep 14;67(Pt 10):o2644–o2645. doi: 10.1107/S1600536811036579

(E)-4-Hydroxy-N′-(3-hydroxy-4-methoxybenzylidene)benzohydrazide

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

PMCID: PMC3201407 PMID: 22064732

Abstract

The molecule of the title benzohydrazide derivative, C₁₅H₁₄N₂O₄, exists in a trans conformation with respect to the C=N double bond and is twisted, the dihedral angle between the two benzene rings being 24.17 (6)°. The methoxy group is almost co-planar with respect to the attached benzene ring [C_m—O—C—C (m = methyl) = −1.45 (17)°]. In the crystal, the molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into sheets parallel to the bc plane. These sheets are further connected into a three-dimensional network by weak C—H⋯O and C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Li & Ban (2009 ▶); Zhang (2011 ▶). For background to and applications of benzohydrazide derivatives, see: Bedia et al. (2006 ▶); Bhole & Bhusari (2009 ▶); Loncle et al. (2004 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M _r = 286.28
Monoclinic,
a = 10.7484 (5) Å
b = 9.4669 (4) Å
c = 15.7198 (5) Å
β = 122.166 (2)°
V = 1354.04 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.42 × 0.29 × 0.19 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.958, T _max = 0.981
16525 measured reflections
3910 independent reflections
3438 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.125
S = 1.03
3910 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.49 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/S1600536811036579/hb6400sup1.cif

e-67-o2644-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036579/hb6400Isup2.hkl

e-67-o2644-Isup2.hkl^{(191.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036579/hb6400Isup3.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
N1—H1A⋯O3ⁱ	0.88	2.30	2.9798 (12)	134
N1—H1A⋯O4ⁱ	0.88	2.53	3.3542 (12)	156
O2—H2A⋯O1ⁱⁱ	0.84	1.89	2.7259 (11)	174
O3—H3A⋯O1ⁱⁱⁱ	0.84	1.88	2.6762 (13)	157
C10—H10A⋯O2^iv	0.95	2.58	3.4786 (14)	158
C15—H15B⋯Cg1^v	0.98	2.85	3.7211 (16)	149

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

Acknowledgments

JH thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, for financial support. The authors 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 a wide variety of biological properties, such as antibacterial (Bhole & Bhusari, 2009), antifungal (Loncle et al., 2004), antitubecular (Bedia et al., 2006) and antiproliferative (Raj et al., 2007) activities.

These interesting properties lead us to synthesize the title compound (I), which contains hydroxyl and methoxy substituents, in order to study and compare its biological properties with other related benzohydrazide derivatives. Herein the crystal structure of (I) is reported.

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₅H₁₄N₂O₄, exists in a trans-configuration with respect to the C8═N2 bond [1.2811 (13) Å] and the torsion angle N1–N2–C8–C9 = 178.77 (9)°. The molecule is twisted with the dihedral angle between the two benzene rings being 24.17 (6)°. Atom O1, C7, N1, N2 and C8 of the middle bridge lie nearly on the same plane with the torsion angle O1–C7–N1–N2 = -3.15 (14)°. The mean plane through this middle bridge makes the dihedral angles of 4.82 (7) and 25.95 (7)° with the C1–C6 and C9–C14 benzene rings, respectively. The methoxy group is almost co-planar with the attached benzene ring with the torsion angle C15–O4–C12–C13 = -1.45 (17)°. Bond distances are of normal values (Allen et al., 1987) and are comparable with related structures (Li & Ban, 2009; Zhang, 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O and O—H···O hydrogen bonds (Table 1) into sheets parallel to the bc plane and these sheets are further connected into three dimensional network. The crystal is stabilized N—H···O and O—H···O hydrogen bonds together with C—H···O weak interaction. C—H···π weak interaction (Table 1) was also observed.

Experimental

The title compound (I) was prepared by dissolving 4-hydroxybenzohydrazide (0.1 mmol, 0.15 g) in ethanol (15 ml). A solution of 3-hydroxy-4-methoxybenzaldehyde (0.1 mmol, 0.15 g) in ethanol (15 ml) was then added slowly to the reaction. The mixture was refluxed for around 5 hr. The solution was then cooled to room temperature. Colorless blocks of (I) were obtained after slow evaporation of the solvent at room temperature after several days, Mp. 516 K (decompose).