(E)-4-Hy­droxy-N′-(3,4,5-trimeth­oxy­benzyl­idene)benzohydrazide

Jirapa Horkaew; Suchada Chantrapromma; Hoong-Kun Fun

doi:10.1107/S1600536811041535

. 2011 Oct 22;67(Pt 11):o2985. doi: 10.1107/S1600536811041535

(E)-4-Hydroxy-N′-(3,4,5-trimethoxybenzylidene)benzohydrazide

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

PMCID: PMC3247387 PMID: 22220005

Abstract

The title benzohydrazide derivative, C₁₇H₁₈N₂O₅, exists in a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 19.41 (5)°. The two methoxy groups at the meta positions of the trimethoxybenzene group are almost coplanar with the ring [C—O—C—C = 1.62 (16) and 178.33 (10)°], whereas the third methoxy group, at the para position, is (+)-synclinal with the ring. In the crystal, molecules are linked by N—H⋯O and bifurcated O—H⋯(N,O) hydrogen bonds, as well as weak C—H⋯O interactions, into sheets lying parallel to the ac plane. A C—H⋯π interaction also occurs.

Related literature

For a related structure and background references to benzohydrazide derivatives, see: Fun et al. (2011 ▶). For related structures, see: Li & Ban (2009 ▶); Zhang (2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₅
M _r = 330.33
Orthorhombic,
a = 14.4623 (8) Å
b = 10.9202 (6) Å
c = 19.5592 (10) Å
V = 3089.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 297 K
0.39 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.979
20210 measured reflections
4500 independent reflections
3777 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.109
S = 1.03
4500 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.32 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/S1600536811041535/hb6444sup1.cif

e-67-o2985-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041535/hb6444Isup2.hkl

e-67-o2985-Isup2.hkl^{(220.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041535/hb6444Isup3.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
O2—H1O2⋯O1ⁱ	0.87 (2)	1.87 (2)	2.6646 (11)	152 (2)
O2—H1O2⋯N2ⁱ	0.87 (2)	2.56 (2)	3.2381 (13)	136.2 (18)
N1—H1N1⋯O4ⁱⁱ	0.874 (17)	2.088 (17)	2.8891 (12)	152.0 (16)
C6—H6A⋯O4ⁱⁱ	0.93	2.51	3.4116 (14)	165
C16—H16B⋯Cg1ⁱⁱⁱ	0.96	2.63	3.4572 (17)	145

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

Acknowledgments

JH thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, and the Graduate School, Prince of Songkla University, for financial support. The authors thank the Prince of Songkla University through the Crystal Materials Research Unit and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

As part of our ongoing studies of benzohydrazide derivatives with possible antibacterial activities (Fun et al., 2011), we now report the synthesis and structure of the title compound, (I). The antibacterial activity of (I) will be reported elsewhere with other related benzohydrazide derivatives.

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₇H₁₈N₂O₅, exists in a trans-configuration with respect to the C8═N2 bond [1.2821 (15) Å] and the torsion angle N1–N2–C8–C9 = 178.33 (10)°. The molecule is twisted with the dihedral angle between the two benzene rings being 19.41 (5)°. The middle fragment is slightly twisted which can be indicated by the torsion angle O1–C7–N1–N2 = -6.63 (15)°. The mean plane through this middle bridge (O1/C7/N1/N2/C8) makes the dihedral angles of 12.06 (6) and 8.39 (6)° with the planes of 4-hydroxyphenyl and 3,4,5-trimethoxyphenyl rings, respectively. The three methoxy groups of the 3,4,5-trimethoxyphenyl unit have two different orientations: the two meta methoxy groups (at atoms C11 and C13 positions) are co-planar with their attached benzene ring with torsion angles C15–O3–C11–C10 = 1.62 (16)° and C17–O5–C13–C12 = 178.33 (10)° whereas the para methoxy is (+)-syn-clinally attached at atom C12 with the torsion angle C16–O4–C12–C11 = 71.28 (15)°. Bond distances are of normal values (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Li & Ban, 2009; Zhang, 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O, O—H···N and O—H···O hydrogen bonds as well as with weak C—H···O interactions (Table 1) into sheets parallel to the ac plane. The crystal structure is stabilized by N—H···O, O—H···N, O—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-hydroxybenzohydrazide (0.1 mmol, 0.15 g) in ethanol (15 ml) and a solution of 3,4,5-trimethoxybenzaldehyde (0.1 mmol, 0.19 g) in ethanol (15 ml) was then added to it0. The mixture was refluxed for around 3 hr and the white solid of the product that appeared was collected by filtration, washed with ethanol and dried in air. Colorless blocks of (I) were obtained after recrystalization from methanol by slow evaporation of the solvent at room temperature after several days, Mp. 532-533 K.