Aqua­bis­[N′-(1,3-dithio­lan-2-ylidene)-2-hy­droxy­benzohydrazidato(0.5−)-κ2N′,O]sodium(I)

Bouchameni, C.; Beghidja, C.; Beghidja, A.; Boutebdja, M.

doi:10.1107/S1600536812023239

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m827-m828

doi:10.1107/S1600536812023239

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Aquabis[N′-(1,3-dithiolan-2-ylidene)-2-hydroxybenzohydrazidato(0.5−)-κ²N′,O]sodium(I)

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

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Mentouri, 25000 Constantine, Algeria
^*Correspondence e-mail: a_beghidja@yahoo.fr

(Received 12 May 2012; accepted 21 May 2012; online 26 May 2012)

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 (H₂L) 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 ).

Experimental

Crystal data

[Na(C₁₀H_9.5N₂O₂S₂)₂(H₂O)]
M_r = 548.68
Monoclinic, C 2
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[F² > 2σ(F²)] = 0.047
wR(F²) = 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)

Table 1
Selected bond lengths (Å)

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

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)
Symmetry codes: (i) -x+1, y, -z+2; (ii) -x+1, y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023239/bq2359sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

For general background to the 2-salicylihydrazono-1,3-dithiolane ligand (H₂L) 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).

Experimental top

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.

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. The intramolecular hydrogen bond is shown as a dashed line. Symmetry code: (a) -x+1, y, -z+1.
	Fig. 2. Mercury view of the crystal structure of title compound along the a axis showing the two-dimensional network via a strong hydrogen bonds through O—H···O atoms.

Aquabis[N'-(1,3-dithiolan-2-ylidene)-2-hydroxybenzohydrazidato(0.5-)- κ²N',O]sodium(I) top

Crystal data top

[Na(C₁₀H_9.5N₂O₂S₂)₂(H₂O)]	F(000) = 568
M_r = 548.68	D_x = 1.538 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2559 reflections
a = 16.6960 (16) Å	θ = 1.0–27.5°
b = 5.9330 (3) Å	µ = 0.46 mm⁻¹
c = 13.5240 (12) Å	T = 298 K
β = 117.804 (3)°	Plates, colorless
V = 1184.99 (17) Å³	0.14 × 0.10 × 0.08 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	2083 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.050
Horizonally mounted graphite crystal monochromator	θ_max = 27.5°, θ_min = 1.7°
Detector resolution: 9 pixels mm^-1	h = −21→21
ϕ scans, and ω scans with κ offsets	k = −6→7
3660 measured reflections	l = −13→17
2463 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0458P)² + 2.9944P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.021
2463 reflections	Δρ_max = 0.33 e Å⁻³
161 parameters	Δρ_min = −0.43 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 970 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (13)

Crystal data top

[Na(C₁₀H_9.5N₂O₂S₂)₂(H₂O)]	V = 1184.99 (17) Å³
M_r = 548.68	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 16.6960 (16) Å	µ = 0.46 mm⁻¹
b = 5.9330 (3) Å	T = 298 K
c = 13.5240 (12) Å	0.14 × 0.10 × 0.08 mm
β = 117.804 (3)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	Δρ_max = 0.33 e Å⁻³
S = 1.00	Δρ_min = −0.43 e Å⁻³
2463 reflections	Absolute structure: Flack (1983), 970 Friedel pairs
161 parameters	Absolute structure parameter: −0.06 (13)
5 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.34168 (7)	0.79324 (19)	0.76027 (8)	0.0330 (3)
S2	0.33261 (8)	1.0904 (2)	0.57897 (10)	0.0388 (4)
Na1	0.50000	0.7068 (4)	0.50000	0.0324 (8)
O1	0.5618 (2)	0.4475 (5)	0.6448 (2)	0.0318 (9)
O2	0.5000 (2)	0.3636 (5)	0.9088 (2)	0.0348 (10)
O3	0.50000	1.0799 (9)	0.50000	0.057 (2)
N1	0.4834 (2)	0.5736 (6)	0.7318 (2)	0.0245 (10)
N2	0.4434 (2)	0.7412 (6)	0.6540 (3)	0.0261 (10)
C1	0.5421 (3)	0.4301 (7)	0.7235 (3)	0.0261 (12)
C2	0.5809 (3)	0.2538 (7)	0.8092 (3)	0.0249 (11)
C3	0.5575 (3)	0.2237 (7)	0.8968 (3)	0.0282 (11)
C4	0.5962 (3)	0.0414 (8)	0.9695 (4)	0.0393 (16)
C5	0.6562 (3)	−0.1025 (9)	0.9594 (4)	0.0400 (16)
C6	0.6809 (3)	−0.0701 (8)	0.8755 (4)	0.0373 (14)
C7	0.6425 (3)	0.1041 (8)	0.8012 (3)	0.0325 (12)
C8	0.3821 (3)	0.8554 (7)	0.6639 (3)	0.0262 (11)
C9	0.2806 (3)	1.0562 (9)	0.7390 (4)	0.0400 (16)
C10	0.2425 (3)	1.1176 (9)	0.6176 (4)	0.0453 (16)
H1	0.47040	0.56020	0.78750	0.0290*
H2	0.512 (8)	0.379 (19)	0.980 (3)	0.0680*	0.500
H3	0.470 (4)	1.171 (8)	0.435 (3)	0.0680*
H4	0.58030	0.01670	1.02760	0.0470*
H5	0.68110	−0.22480	1.01000	0.0480*
H6	0.72380	−0.16700	0.86960	0.0450*
H7	0.65820	0.12360	0.74260	0.0390*
H9A	0.23110	1.03850	0.75920	0.0480*
H9B	0.32190	1.17610	0.78640	0.0480*
H10A	0.21950	1.27430	0.60530	0.0540*
H10B	0.19180	1.01580	0.57130	0.0540*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0373 (6)	0.0381 (6)	0.0316 (5)	0.0081 (5)	0.0228 (5)	0.0031 (5)
S2	0.0465 (7)	0.0349 (6)	0.0353 (6)	0.0119 (5)	0.0194 (5)	0.0097 (5)
Na1	0.0457 (14)	0.0278 (13)	0.0329 (12)	0.0000	0.0260 (11)	0.0000
O1	0.0435 (17)	0.0330 (17)	0.0300 (15)	0.0067 (13)	0.0265 (14)	0.0027 (12)
O2	0.0449 (18)	0.0407 (19)	0.0274 (15)	0.0150 (15)	0.0240 (15)	0.0072 (13)
O3	0.113 (5)	0.029 (3)	0.040 (3)	0.0000	0.044 (3)	0.0000
N1	0.0286 (17)	0.0287 (18)	0.0195 (15)	0.0012 (15)	0.0139 (13)	0.0016 (14)
N2	0.0321 (18)	0.0259 (19)	0.0225 (16)	0.0035 (15)	0.0145 (14)	0.0029 (12)
C1	0.030 (2)	0.028 (2)	0.025 (2)	−0.0002 (17)	0.0167 (17)	−0.0024 (16)
C2	0.0249 (18)	0.027 (2)	0.0217 (17)	−0.0008 (16)	0.0100 (14)	−0.0048 (15)
C3	0.030 (2)	0.033 (2)	0.0213 (18)	0.0045 (17)	0.0116 (16)	0.0001 (16)
C4	0.046 (3)	0.041 (3)	0.029 (2)	0.008 (2)	0.016 (2)	0.0058 (18)
C5	0.045 (3)	0.036 (3)	0.029 (2)	0.012 (2)	0.009 (2)	0.0066 (19)
C6	0.036 (2)	0.033 (3)	0.037 (2)	0.011 (2)	0.012 (2)	−0.002 (2)
C7	0.033 (2)	0.036 (2)	0.033 (2)	−0.001 (2)	0.0193 (18)	−0.005 (2)
C8	0.029 (2)	0.030 (2)	0.0190 (18)	−0.0005 (16)	0.0108 (16)	0.0010 (15)
C9	0.038 (2)	0.044 (3)	0.043 (3)	0.009 (2)	0.023 (2)	−0.003 (2)
C10	0.040 (2)	0.045 (3)	0.045 (3)	0.022 (2)	0.015 (2)	0.003 (2)

Geometric parameters (Å, º) top

S1—C8	1.764 (5)	N1—H1	0.8800
S1—C9	1.812 (6)	C1—C2	1.469 (6)
S2—C8	1.750 (4)	C2—C3	1.421 (6)
S2—C10	1.815 (6)	C2—C7	1.401 (7)
Na1—O1	2.320 (3)	C3—C4	1.401 (6)
Na1—O3	2.214 (6)	C4—C5	1.371 (8)
Na1—N2	2.666 (4)	C5—C6	1.390 (7)
Na1—O1ⁱ	2.320 (3)	C6—C7	1.374 (6)
Na1—N2ⁱ	2.666 (4)	C9—C10	1.503 (7)
O1—C1	1.256 (5)	C4—H4	0.9500
O2—C3	1.335 (6)	C5—H5	0.9500
O2—H2	0.89 (5)	C6—H6	0.9500
O3—H3ⁱ	0.95 (4)	C7—H7	0.9500
O3—H3	0.95 (4)	C9—H9A	0.9900
N1—N2	1.373 (5)	C9—H9B	0.9900
N1—C1	1.342 (6)	C10—H10A	0.9900
N2—C8	1.285 (6)	C10—H10B	0.9900

S1···N1	2.880 (4)	C3···H1	2.5100
S1···C4ⁱⁱ	3.614 (5)	C3···H2^ix	2.60 (11)
S2···C10ⁱⁱⁱ	3.660 (5)	C4···H9B^xii	3.0300
S2···O3	3.4263 (15)	C4···H2^ix	2.98 (12)
S1···H1	2.4300	C4···H4^ix	2.9700
S1···H7^iv	3.1300	C6···H5^xiii	2.9300
S1···H4ⁱⁱ	2.8600	C7···H5^xiii	3.0300
S2···H10Aⁱⁱⁱ	2.9100	C7···H3^viii	2.88 (4)
S2···H10B^v	3.1500	C9···H6^xiv	2.8800
Na1···C10^vi	3.633 (6)	C9···H4ⁱⁱ	2.9300
Na1···C10ⁱⁱⁱ	3.633 (6)	H1···S1	2.4300
Na1···H10B^vi	3.1000	H1···O2	1.8800
Na1···H10Bⁱⁱⁱ	3.1000	H1···C3	2.5100
O1···O3^vii	2.788 (5)	H1···H2	2.5900
O1···N2	2.681 (5)	H2···H1	2.5900
O1···C9^vi	3.323 (7)	H2···H4	2.3800
O1···O3^viii	2.788 (5)	H2···O2^ix	1.61 (9)
O1···C10^vi	3.360 (7)	H2···C3^ix	2.60 (11)
O2···C4^ix	3.378 (6)	H2···C4^ix	2.98 (12)
O2···N1	2.596 (4)	H3···O1^xi	1.90 (4)
O2···C3^ix	3.298 (5)	H3···C1^xi	2.57 (4)
O2···O2^ix	2.467 (4)	H3···C2^xi	3.04 (4)
O3···O1^x	2.788 (5)	H3···C7^xi	2.88 (4)
O3···S2ⁱ	3.4263 (15)	H3···H7^xi	2.3700
O3···O1^xi	2.788 (5)	H4···H2	2.3800
O3···S2	3.4263 (15)	H4···S1^xii	2.8600
O1···H7	2.4600	H4···O2^ix	2.8000
O1···H10B^vi	2.8100	H4···C4^ix	2.9700
O1···H3^viii	1.90 (4)	H4···C9^xii	2.9300
O1···H9A^vi	2.5700	H4···H4^ix	2.4200
O2···H2^ix	1.61 (8)	H4···H9B^xii	2.4600
O2···H9B^vii	2.8700	H5···C6^xv	2.9300
O2···H4^ix	2.8000	H5···C7^xv	3.0300
O2···H1	1.8800	H6···C9^xvi	2.8800
N1···S1	2.880 (4)	H6···H9A^xvi	2.3400
N1···O1	2.257 (5)	H6···H9B^xvi	2.5600
N1···O2	2.596 (4)	H7···O1	2.4600
N2···O1	2.681 (5)	H7···H3^viii	2.3700
C3···O2^ix	3.298 (5)	H7···S1^vi	3.1300
C4···O2^ix	3.378 (6)	H9A···O1^iv	2.5700
C4···S1^xii	3.614 (5)	H9A···C1^iv	3.0300
C4···C9^xii	3.495 (7)	H9A···H6^xiv	2.3400
C9···O1^iv	3.323 (7)	H9B···O2^x	2.8700
C9···C4ⁱⁱ	3.495 (7)	H9B···C4ⁱⁱ	3.0300
C10···O1^iv	3.360 (7)	H9B···H4ⁱⁱ	2.4600
C10···Na1^iv	3.633 (6)	H9B···H6^xiv	2.5600
C10···Na1^v	3.633 (6)	H10A···S2^v	2.9100
C10···S2^v	3.660 (5)	H10B···Na1^iv	3.1000
C1···H9A^vi	3.0300	H10B···O1^iv	2.8100
C1···H3^viii	2.57 (4)	H10B···S2ⁱⁱⁱ	3.1500
C2···H3^viii	3.04 (4)	H10B···Na1^v	3.1000

C8—S1—C9	94.8 (2)	O2—C3—C2	121.1 (4)
C8—S2—C10	94.8 (2)	O2—C3—C4	121.2 (4)
O1—Na1—O3	131.54 (8)	C3—C4—C5	122.0 (5)
O1—Na1—N2	64.63 (11)	C4—C5—C6	120.3 (5)
O1—Na1—O1ⁱ	96.91 (13)	C5—C6—C7	119.1 (5)
O1—Na1—N2ⁱ	122.01 (13)	C2—C7—C6	122.0 (4)
O3—Na1—N2	85.61 (9)	S1—C8—S2	115.2 (3)
O1ⁱ—Na1—O3	131.54 (8)	S1—C8—N2	124.4 (3)
O3—Na1—N2ⁱ	85.61 (9)	S2—C8—N2	120.5 (3)
O1ⁱ—Na1—N2	122.01 (13)	S1—C9—C10	107.6 (4)
N2—Na1—N2ⁱ	171.22 (15)	S2—C10—C9	107.9 (4)
O1ⁱ—Na1—N2ⁱ	64.63 (11)	C3—C4—H4	119.00
Na1—O1—C1	125.5 (3)	C5—C4—H4	119.00
C3—O2—H2	113 (8)	C4—C5—H5	120.00
Na1—O3—H3	125 (3)	C6—C5—H5	120.00
Na1—O3—H3ⁱ	125 (3)	C5—C6—H6	120.00
H3—O3—H3ⁱ	111 (4)	C7—C6—H6	120.00
N2—N1—C1	120.6 (3)	C2—C7—H7	119.00
Na1—N2—N1	108.7 (2)	C6—C7—H7	119.00
Na1—N2—C8	135.3 (3)	S1—C9—H9A	110.00
N1—N2—C8	115.4 (4)	S1—C9—H9B	110.00
C1—N1—H1	120.00	C10—C9—H9A	110.00
N2—N1—H1	120.00	C10—C9—H9B	110.00
N1—C1—C2	117.2 (4)	H9A—C9—H9B	108.00
O1—C1—N1	120.6 (4)	S2—C10—H10A	110.00
O1—C1—C2	122.3 (4)	S2—C10—H10B	110.00
C1—C2—C7	117.4 (4)	C9—C10—H10A	110.00
C3—C2—C7	118.8 (4)	C9—C10—H10B	110.00
C1—C2—C3	123.8 (4)	H10A—C10—H10B	108.00
C2—C3—C4	117.8 (4)

C9—S1—C8—S2	−11.2 (3)	N2—N1—C1—C2	−179.2 (4)
C9—S1—C8—N2	168.7 (4)	Na1—N2—C8—S1	163.7 (2)
C8—S1—C9—C10	35.8 (4)	Na1—N2—C8—S2	−16.4 (6)
C10—S2—C8—S1	−11.6 (3)	N1—N2—C8—S1	−5.8 (5)
C10—S2—C8—N2	168.5 (4)	N1—N2—C8—S2	174.1 (3)
C8—S2—C10—C9	36.2 (4)	O1—C1—C2—C3	−177.5 (4)
O3—Na1—O1—C1	60.2 (4)	O1—C1—C2—C7	0.7 (6)
N2—Na1—O1—C1	2.4 (3)	N1—C1—C2—C3	2.1 (6)
O1ⁱ—Na1—O1—C1	−119.8 (3)	N1—C1—C2—C7	−179.8 (4)
N2ⁱ—Na1—O1—C1	175.9 (3)	C1—C2—C3—O2	−2.7 (7)
O1—Na1—N2—N1	−1.8 (2)	C1—C2—C3—C4	176.8 (4)
O1—Na1—N2—C8	−171.8 (5)	C7—C2—C3—O2	179.1 (4)
O3—Na1—N2—N1	−142.4 (2)	C7—C2—C3—C4	−1.4 (6)
O3—Na1—N2—C8	47.6 (4)	C1—C2—C7—C6	−178.4 (4)
O1ⁱ—Na1—N2—N1	80.2 (3)	C3—C2—C7—C6	−0.1 (7)
O1ⁱ—Na1—N2—C8	−89.8 (4)	O2—C3—C4—C5	−179.2 (4)
Na1—O1—C1—N1	−2.7 (6)	C2—C3—C4—C5	1.3 (7)
Na1—O1—C1—C2	176.9 (3)	C3—C4—C5—C6	0.3 (8)
C1—N1—N2—Na1	1.5 (4)	C4—C5—C6—C7	−1.8 (8)
C1—N1—N2—C8	173.7 (4)	C5—C6—C7—C2	1.7 (7)
N2—N1—C1—O1	0.4 (6)	S1—C9—C10—S2	−48.2 (4)

Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+1, y+1, −z+2; (iii) −x+1/2, y−1/2, −z+1; (iv) x−1/2, y+1/2, z; (v) −x+1/2, y+1/2, −z+1; (vi) x+1/2, y−1/2, z; (vii) x, y−1, z; (viii) −x+1, y−1, −z+1; (ix) −x+1, y, −z+2; (x) x, y+1, z; (xi) −x+1, y+1, −z+1; (xii) −x+1, y−1, −z+2; (xiii) −x+3/2, y+1/2, −z+2; (xiv) x−1/2, y+3/2, z; (xv) −x+3/2, y−1/2, −z+2; (xvi) x+1/2, y−3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1	0.8800	2.4300	2.880 (4)	112.00
N1—H1···O2	0.8800	1.8800	2.596 (4)	137.00
O2—H2···O2^ix	0.89 (5)	1.61 (9)	2.467 (4)	160 (14)
O3—H3···O1^xi	0.95 (4)	1.90 (4)	2.788 (5)	155 (4)
C4—H4···S1^xii	0.95	2.86	3.614 (5)	137
C7—H7···O1	0.95	2.46	2.790 (5)	100
C9—H9A···O1^iv	0.99	2.57	3.323 (7)	133

Symmetry codes: (iv) x−1/2, y+1/2, z; (ix) −x+1, y, −z+2; (xi) −x+1, y+1, −z+1; (xii) −x+1, y−1, −z+2.

Experimental details

Crystal data
Chemical formula	[Na(C₁₀H_9.5N₂O₂S₂)₂(H₂O)]
M_r	548.68
Crystal system, space group	Monoclinic, C2
Temperature (K)	298
a, b, c (Å)	16.6960 (16), 5.9330 (3), 13.5240 (12)
β (°)	117.804 (3)
V (Å³)	1184.99 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.14 × 0.10 × 0.08

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3660, 2463, 2083
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.00
No. of reflections	2463
No. of parameters	161
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.43
Absolute structure	Flack (1983), 970 Friedel pairs
Absolute structure parameter	−0.06 (13)

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.8800	1.8800	2.596 (4)	137.00
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)

Symmetry codes: (i) −x+1, y, −z+2; (ii) −x+1, y+1, −z+1.

Acknowledgements

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

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