(E)-2-Meth­oxy-N′-(2,4,6-trihy­droxy­benzyl­idene)benzohydrazide

Muhammad Taha; M Syukri Baharudin; Nor Hadiani Ismail; Syed Adnan Ali Shah; Sammer Yousuf

doi:10.1107/S1600536813001748

. 2013 Jan 23;69(Pt 2):o277. doi: 10.1107/S1600536813001748

(E)-2-Methoxy-N′-(2,4,6-trihydroxybenzylidene)benzohydrazide

Muhammad Taha ^a, M Syukri Baharudin ^a, Nor Hadiani Ismail ^b, Syed Adnan Ali Shah ^a,^c, Sammer Yousuf ^d,^*

PMCID: PMC3569804 PMID: 23424550

Abstract

In the title hydrazone derivative, C₁₅H₁₄N₂O₅, the benzene rings are twisted by 7.55 (8)° with respect to each other. The azomethine double bond adopts an E conformation. The molecular structure is stabilized by intramolecular O—H⋯N and N—H⋯O hydrogen bonds, generating S6 ring motifs. In the crystal, molecules are linked into a three-dimensional network by O—H⋯O hydrogen bonds.

Related literature

For applications and biological activity of Schiff bases, see: Khan et al. (2011 ▶, 2012 ▶); Rada & Leto (2008 ▶); Almasirad et al. (2006 ▶). For related structures, see: Taha et al. (2012 ▶); Shen et al. (2012 ▶). graphic file with name e-69-0o277-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₄N₂O₅
M _r = 302.28
Orthorhombic,
a = 6.4580 (4) Å
b = 13.4772 (8) Å
c = 16.3169 (9) Å
V = 1420.15 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.34 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.964, T _max = 0.978
8414 measured reflections
2643 independent reflections
2481 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.080
S = 1.07
2643 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(19.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001748/rz5037sup1.cif

e-69-0o277-sup1.cif^{(19.1KB, cif)}

Click here for additional data file.^{(129.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001748/rz5037Isup2.hkl

e-69-0o277-Isup2.hkl^{(129.8KB, hkl)}

Click here for additional data file.^{(2.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001748/rz5037Isup3.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
O1—H1A⋯N1	0.84 (3)	1.88 (2)	2.6243 (18)	147 (2)
N2—H2A⋯O5	0.851 (19)	1.923 (19)	2.5981 (18)	135.4 (17)
O3—H2B⋯O4ⁱ	0.86 (2)	1.79 (2)	2.6452 (17)	175 (2)
O2—H3A⋯O1ⁱⁱ	0.93 (3)	1.92 (3)	2.8513 (18)	172 (3)

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

supplementary crystallographic information

Comment

Hydrazone derivatives represent an important class of organic compounds. Due to their biological activities (Khan et al., 2011, 2012; Rada & Leto, 2008; Almasirad et al., 2006) the research for this class of compounds is an area of great interest. The title compound is a hydrazone derivatives synthesized as a part of our ongoing research to establish a library of bioactive hydrazone derivatives.

The structure of the title compound (Fig. 1) is similar to that of the previously published compound N'-(3,4-dihydroxybenzylidene)-2- methoxybenzohydrazide (Shen et al., 2012) with the difference that the 3,4-dihydroxy benzene ring is replaced by a 2,4,6-trihydroxy benzene ring (C1–C6). The dihedral angle between the two benzene rings is 7.55 (8)°. The bond lengths and angles were found to be similar to those observed in structurally related benzohydrazide derivatives (Taha et al., 2012; Shen et al., 2012). Intramolecular O1—H1A···N1 and N2—H2A···O5 hydrogen bonds play an important role to stabilize the E configuration of the azomethine olefinic bond (Table 1). The crystal structure (Fig. 2) is stabilized by intermolecular O3—H2B···O4 and O2—H3A···O1 interactions to form a three-dimensional network.

Experimental

The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2,4,6-trihydroxy-5-methoxybenzaldehyde (0.304 g, 2 mmol) in methanol along with a catalytical amount of acetic acid for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated by vacuum to afford the crude product which was recrystallized by dissolving in methanol at room temperature. Needle-shaped crystals were obtained on slow evaporation of the solvent (0.496 g, 82% yield). All chemicals were purchased by Sigma Aldrich, Germany.