Aqua-bis-[N'-(1,3-dithio-lan-2-ylidene)-2-hy-droxy-benzohydrazidato(0.5-)-κ(2)N',O]sodium(I).

The title compound, [Na(C(10)H(9.5)N(2)O(2)S(2))(2)(H(2)O)], is a mol-ecular sodium complex with N'-(1,3-dithio-lan-2-yl)-2-hy-droxy-benzohydrazide ligands with the negative charge spread evenly over both, and a water mol-ecule. 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. Intra-molecular N-H⋯O hydrogen bonds occur. Mol-ecules 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 inter-linked 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 ▶).

Experimental

Crystal data

[Na(C10H9.5N2O2S2)2(H2O)]

M = 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

Δρmax = 0.33 e Å−3

Δρmin = −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.

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

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

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

[Na(C10H9.5N2O2S2)2(H2O)]	F(000) = 568
Mr = 548.68	Dx = 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

Nonius KappaCCD diffractometer	2083 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.050
Horizonally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0458P)2 + 2.9944P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.021
2463 reflections	Δρmax = 0.33 e Å−3
161 parameters	Δρmin = −0.43 e Å−3
5 restraints	Absolute structure: Flack (1983), 970 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (13)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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···H2ix	2.60 (11)
S2···C10iii	3.660 (5)	C4···H9Bxii	3.0300
S2···O3	3.4263 (15)	C4···H2ix	2.98 (12)
S1···H1	2.4300	C4···H4ix	2.9700
S1···H7iv	3.1300	C6···H5xiii	2.9300
S1···H4ii	2.8600	C7···H5xiii	3.0300
S2···H10Aiii	2.9100	C7···H3viii	2.88 (4)
S2···H10Bv	3.1500	C9···H6xiv	2.8800
Na1···C10vi	3.633 (6)	C9···H4ii	2.9300
Na1···C10iii	3.633 (6)	H1···S1	2.4300
Na1···H10Bvi	3.1000	H1···O2	1.8800
Na1···H10Biii	3.1000	H1···C3	2.5100
O1···O3vii	2.788 (5)	H1···H2	2.5900
O1···N2	2.681 (5)	H2···H1	2.5900
O1···C9vi	3.323 (7)	H2···H4	2.3800
O1···O3viii	2.788 (5)	H2···O2ix	1.61 (9)
O1···C10vi	3.360 (7)	H2···C3ix	2.60 (11)
O2···C4ix	3.378 (6)	H2···C4ix	2.98 (12)
O2···N1	2.596 (4)	H3···O1xi	1.90 (4)
O2···C3ix	3.298 (5)	H3···C1xi	2.57 (4)
O2···O2ix	2.467 (4)	H3···C2xi	3.04 (4)
O3···O1x	2.788 (5)	H3···C7xi	2.88 (4)
O3···S2i	3.4263 (15)	H3···H7xi	2.3700
O3···O1xi	2.788 (5)	H4···H2	2.3800
O3···S2	3.4263 (15)	H4···S1xii	2.8600
O1···H7	2.4600	H4···O2ix	2.8000
O1···H10Bvi	2.8100	H4···C4ix	2.9700
O1···H3viii	1.90 (4)	H4···C9xii	2.9300
O1···H9Avi	2.5700	H4···H4ix	2.4200
O2···H2ix	1.61 (8)	H4···H9Bxii	2.4600
O2···H9Bvii	2.8700	H5···C6xv	2.9300
O2···H4ix	2.8000	H5···C7xv	3.0300
O2···H1	1.8800	H6···C9xvi	2.8800
N1···S1	2.880 (4)	H6···H9Axvi	2.3400
N1···O1	2.257 (5)	H6···H9Bxvi	2.5600
N1···O2	2.596 (4)	H7···O1	2.4600
N2···O1	2.681 (5)	H7···H3viii	2.3700
C3···O2ix	3.298 (5)	H7···S1vi	3.1300
C4···O2ix	3.378 (6)	H9A···O1iv	2.5700
C4···S1xii	3.614 (5)	H9A···C1iv	3.0300
C4···C9xii	3.495 (7)	H9A···H6xiv	2.3400
C9···O1iv	3.323 (7)	H9B···O2x	2.8700
C9···C4ii	3.495 (7)	H9B···C4ii	3.0300
C10···O1iv	3.360 (7)	H9B···H4ii	2.4600
C10···Na1iv	3.633 (6)	H9B···H6xiv	2.5600
C10···Na1v	3.633 (6)	H10A···S2v	2.9100
C10···S2v	3.660 (5)	H10B···Na1iv	3.1000
C1···H9Avi	3.0300	H10B···O1iv	2.8100
C1···H3viii	2.57 (4)	H10B···S2iii	3.1500
C2···H3viii	3.04 (4)	H10B···Na1v	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)

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···O2ix	0.89 (5)	1.61 (9)	2.467 (4)	160 (14)
O3—H3···O1xi	0.95 (4)	1.90 (4)	2.788 (5)	155 (4)
C4—H4···S1xii	0.95	2.86	3.614 (5)	137
C7—H7···O1	0.95	2.46	2.790 (5)	100
C9—H9A···O1iv	0.99	2.57	3.323 (7)	133

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) ; (ii) .