Aqua­bis­[N′-(1,3-dithio­lan-2-ylidene)-2-hy­droxy­benzohydrazidato(0.5−)-κ2 N′,O]sodium(I)

Chahra Bouchameni; Chahrazed Beghidja; Adel Beghidja; Mehdi Boutebdja

doi:10.1107/S1600536812023239

. 2012 May 26;68(Pt 6):m827–m828. doi: 10.1107/S1600536812023239

Aquabis[N′-(1,3-dithiolan-2-ylidene)-2-hydroxybenzohydrazidato(0.5−)-κ² N′,O]sodium(I)

Chahra Bouchameni ^a, Chahrazed Beghidja ^a, Adel Beghidja ^a,^*, Mehdi Boutebdja ^a

PMCID: PMC3379147 PMID: 22719368

Abstract

The title compound, [Na(C₁₀H_9.5N₂O₂S₂)₂(H₂O)], is a molecular sodium complex with N′-(1,3-dithiolan-2-yl)-2-hydroxybenzohydrazide ligands with the negative charge spread evenly over both, and a water molecule. The Na^I ion coordination is distorted trigonal–bipyramidal, formed by two N and three O atoms, with the Na^I ion lying on a twofold rotation axis. Intramolecular N—H⋯O hydrogen bonds occur. Molecules pack as discrete units and the crystal packing is stabilized by strong O—H⋯O hydrogen bonds, which give rise to chains along [010]; the chains are interlinked by strong O—H⋯O hydrogen bonds.

Related literature

For general background to the 2-salicylihydrazono-1,3-dithiolane ligand (H₂ L) and its metal complexes, see: Beghidja et al. (2005 ▶, 2006 ▶); Bouchameni et al. (2011 ▶). For background to dithiocarbazates, see: Wang et al. (2002 ▶); Zhou et al. (2007 ▶) and for their biological activity, see: Tarafder et al. (2000 ▶, 2001 ▶). graphic file with name e-68-0m827-scheme1.jpg

Experimental

Crystal data

[Na(C₁₀H_9.5N₂O₂S₂)₂(H₂O)]
M _r = 548.68
Monoclinic,
a = 16.6960 (16) Å
b = 5.9330 (3) Å
c = 13.5240 (12) Å
β = 117.804 (3)°
V = 1184.99 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 298 K
0.14 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
3660 measured reflections
2463 independent reflections
2083 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.126
S = 1.00
2463 reflections
161 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ▶), 970 Friedel pairs
Flack parameter: −0.06 (13)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023239/bq2359sup1.cif

e-68-0m827-sup1.cif^{(28.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023239/bq2359Isup2.hkl

e-68-0m827-Isup2.hkl^{(118.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected bond lengths (Å).

Na1—O1	2.320 (3)
Na1—O3	2.214 (6)
Na1—N2	2.666 (4)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.88	1.88	2.596 (4)	137
O2—H2⋯O2ⁱ	0.89 (5)	1.61 (9)	2.467 (4)	160 (14)
O3—H3⋯O1ⁱⁱ	0.95 (4)	1.90 (4)	2.788 (5)	155 (4)

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

Acknowledgments

The authors thank the MESRS (Algeria) for financial support (PNR project).

supplementary crystallographic information

Comment

Dithiocarbazate R—NH₂NHCS₂ (DTC) and its substituted compounds remain of interest to researchers because of their wide variation in structure and properties (Zhou et al., 2007; Wang et al., 2002). Some of these compounds have been widely studies for their antibacterial and antifungal activities (Tarafder et al., 2000; Tarafder et al., 2001). The ligand H₂L was synthesized as previously described (Beghidja et al., 2005). The molecular structure of the title compound is illustrated in Fig. 1. The sodium cation is chelated by two H_1.5L^-1/2 bidentate anions coordinated by the hydrazide group via O1 and N2 atoms. Na1—O1 = 2.316 (3) Å, Na1—N2 = 2.664 (3) Å. The geometry around the metal is a distorted trigonal bipyramid with a water molecule lying in the axial position through O3. Na1—O3 = 2.213 (5) Å. The crystal structure can be described as a one-dimensional set of chains, interlinked by strong hydrogen-bonds type O—H···O, along the b axis, between O3—H3···O1. These chains are interconnected along the c axis via strong hydrogen-bonds type O—H···O between O2—H2···O2 (Fig 2).

Experimental

The reaction of H₂L (0.05 g, 2 x 10 ^-4 mol) with Mn(OH)₃ (0.0106 g, 10 ^-4 mol) and NaOH (0.01 g, 2 x 10 ^-4 mol) in ethanol solution leads to a yellow solution which was left to stand undisturbed at room temperature. Several days later, x-ray quality colorless single crystals were obtained by slow evaporation, which were filtrated and characterized.