(E)-N′-(3,4-Dihy­droxy­benzyl­idene)-2,4-dimethyl­benzohydrazide monohydrate

Muhammad Taha; Nor Hadiani Ismail; Faridahanim Mohd Jaafar; Ahmad Nazif Aziz; Sammer Yousuf

doi:10.1107/S1600536813005692

. 2013 Mar 6;69(Pt 4):o490. doi: 10.1107/S1600536813005692

(E)-N′-(3,4-Dihydroxybenzylidene)-2,4-dimethylbenzohydrazide monohydrate

Muhammad Taha ^a, Nor Hadiani Ismail ^b, Faridahanim Mohd Jaafar ^b, Ahmad Nazif Aziz ^a,^c, Sammer Yousuf ^d,^*

PMCID: PMC3629524 PMID: 23634042

Abstract

In the title compound, C₁₆H₁₆N₂O₃·H₂O, the dihedral angle between the benzene rings is 30.27 (7)°. In the crystal, the components are linked by N—H⋯O, O—H⋯O and C—H⋯O interactions into a three-dimensional network.

Related literature

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012 ▶); Khan et al. (2012 ▶). For the crystal structures of related compounds, see: Taha et al. (2012 ▶); Baharudin et al. (2012 ▶). graphic file with name e-69-0o490-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O₃·H₂O
M _r = 302.32
Monoclinic,
a = 8.1373 (3) Å
b = 13.9025 (5) Å
c = 13.7886 (5) Å
β = 92.913 (1)°
V = 1557.87 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.973, T _max = 0.991
9012 measured reflections
2897 independent reflections
2535 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.111
S = 1.05
2897 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 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.^{(19.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005692/pv2622sup1.cif

e-69-0o490-sup1.cif^{(19.5KB, cif)}

Click here for additional data file.^{(142.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005692/pv2622Isup2.hkl

e-69-0o490-Isup2.hkl^{(142.2KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813005692/pv2622Isup3.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
O1W—H1W1⋯N2ⁱ	0.87 (2)	2.20 (2)	3.059 (2)	169 (2)
O1W—H2W1⋯O1	0.94 (2)	2.01 (2)	2.935 (2)	173 (2)
N1—H1A⋯O3ⁱⁱ	0.91 (2)	2.08 (2)	2.962 (2)	163 (2)
O2—H2A⋯O1ⁱ	0.88 (2)	1.94 (2)	2.791 (2)	162 (2)
O3—H3A⋯O1W ⁱⁱⁱ	0.85 (2)	1.79 (2)	2.629 (2)	172 (2)
C8—H8A⋯O3ⁱⁱ	0.93	2.58	3.382 (2)	145
C15—H15B⋯O2ⁱ	0.96	2.52	3.351 (2)	144

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

Acknowledgments

The authors thank the Research Management Institute of UiTM for financial support under the Dana Kecemerlangan Grant Scheme [grant No. 600-RMI/DANA 5/3 RIF (143/2012)].

supplementary crystallographic information

Comment

Structurally diverse range of benzohydrazides have been extensively studied in order to explore the structural features that may be responsible for different biological activities (Musharraf et al., 2012; Khan et al., 2012). The title compound is yet another benzohydrazide monohydrate, obtained as a part of our ongoing research that has been studied by X-ray crystallographic method and reported in this article.

In the title compound (Fig. 1) dimethyl and dihydroxy substituted benzene rings (C1–C6 and C9–C14, respectively) are each planner with a dihedral angle 30.27 (7)° between their mean-planes. The azomethine double bond, N2═C8 (1.2729 (19) Å) adopts an E configuration. The bond lengths and angle are similar to the corresponding bond lengths and angles reported in structurally related benzohydrazide derivatives (Taha et al., 2012; Baharudin et al., 2012). The crystal structure is stabilized by N1—H1A···N2, O2—H2A···O1, C8—H8A···O3 and C15—H15B···O2 intermolecular interactions. The ineteractions further extend the structure to a three dimentional network via O1W—H2W1···O1, O1W—H1A···O3 and O3—H3A···O1W interactions involving the water of hydration (Table 2 and Fig. 2).

Experimental

The title compound was synthesized by reacting (0.328 g, 2 mmol) 2,4-dimethylbenzohydrazide and (0.276 g, 2 mmol) 3,4-dihydroxybenzaldehyde as starting meterial under the same conditions and solvents as described previously for the synthesis of benzohydrazides (Taha et al., 2012). The title compound was recrystalized by dissolving in methanol to obtain colorless needles (0.499 g, 88% yield). All chemicals were purchased by Sigma Aldrich Germany.