(E)-4-Amino-N′-(2-hy­droxy-5-meth­oxy­benzyl­idene)benzohydrazide monohydrate

Hadi Kargar; Reza Kia; Muhammad Nawaz Tahir

doi:10.1107/S1600536812026633

. 2012 Jul 4;68(Pt 8):o2321–o2322. doi: 10.1107/S1600536812026633

(E)-4-Amino-N′-(2-hydroxy-5-methoxybenzylidene)benzohydrazide monohydrate

Hadi Kargar ^a, Reza Kia ^b,^*,^‡, Muhammad Nawaz Tahir ^c,^*

PMCID: PMC3414187 PMID: 22904794

Abstract

In the title compound, C₁₅H₁₅N₃O₃·H₂O, the hydazide Schiff base molecule shows an E conformation around the C=N bond. An intramolecular O—H⋯N hydrogen bond makes an S(6) ring motif. The dihedral angle between the substituted phenyl rings is 23.40 (11)°. The water molecule mediates linking of neighbouring molecules through O—H⋯(O,O) hydrogen bonds into infinite chains along the a axis, which are further connected together through N—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001). C—H⋯O interactions aso occur.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶); Kargar et al. (2012a ▶,b ▶).

Experimental

Crystal data

C₁₅H₁₅N₃O₃·H₂O
M _r = 303.32
Monoclinic,
a = 4.7376 (5) Å
b = 13.270 (2) Å
c = 11.7265 (16) Å
β = 98.459 (4)°
V = 729.18 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.972, T _max = 0.982
6511 measured reflections
1679 independent reflections
1433 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.085
S = 1.03
1679 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026633/bq2366sup1.cif

e-68-o2321-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026633/bq2366Isup2.hkl

e-68-o2321-Isup2.hkl^{(82.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812026633/bq2366Isup3.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⋯O1ⁱ	0.92	2.00	2.926 (3)	174
O2—H2⋯N3	0.93	1.85	2.650 (3)	143
O1W—H2W1⋯O1ⁱⁱ	0.83	1.95	2.787 (3)	176
N2—H2N⋯O1W	0.95	2.15	3.084 (3)	167
N1—H1N1⋯O3ⁱⁱⁱ	0.93	2.25	3.043 (3)	143
N1—H2N1⋯O2ⁱ	0.99	2.17	3.141 (3)	169
C2—H2A⋯O1W	0.93	2.45	3.351 (3)	163
C8—H8A⋯O1W	0.93	2.56	3.368 (3)	146

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

Acknowledgments

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan for the research facility.

supplementary crystallographic information

Comment

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide have been reported earlier (Kargar et al., 2012a,b; Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). In order to explore the structure of the new Schiff base derivatives, the title compound was prepared and characterized crystallographically.

The asymmetric unit of the title compound, Fig. 1, comprises a molecule of the title hydazide Schiff base and a water molecule of crystallization. It shows E conformation around C═N bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Kargar et al., 2012a,b; Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). Intramolecular O—H···N hydrogen bond makes S(6) ring motif (Bernstein et al., 1995). The dihedral angle between the substituted phenyl rings is 23.40 (11)Å. The water molecule mediates linking of the neighboring molecules through O—H···(O, O) hydrogen bondings into infinite chains along the a axis which are further connected together through N—H···O hydrogen bonds, forming two-dimensional network parallel to (0 0 1) [Fig. 2].

Experimental

The title compound was synthesized by adding 1 mmol of methyl 4-aminobenzoate to a solution of 5-methoxysalicylaldehyde (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 50 min and after cooling to room temperature a light-yellow precipitate was filtered and washed with diethylether and dried in air. white prismatic crystals of the title compound, suitable for X-ray structure analysis, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.