catena-Poly[[aqua­sodium(I)]-μ-[2,2′-(disulfanedi­yl)bis­(pyridine N-oxide)]-μ-(pyridine-2-thiol­ato 1-oxide)]

Ravindran Durai Nayagam, B.; Jebas, S.R.; Devadasan, J.J.; Murugesan, R.; Schollmeyer, D.

doi:10.1107/S1600536810000073

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages m142-m143

https://doi.org/10.1107/S1600536810000073

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catena-Poly[[aquasodium(I)]-μ-[2,2′-(disulfanediyl)bis(pyridine N-oxide)]-μ-(pyridine-2-thiolato 1-oxide)]

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b J. Jebaraj Devadasan,^c R. Murugesan ^d and Dieter Schollmeyer ^e

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India, ^bDepartment of Physics, Sethupathy Government Arts College, Ramanathapuram 623 502, Tamilnadu, India, ^cDepartment of Physics, Popes College, Sawyerpuram 628 251, Tamilnadu, India, ^dDepartment of Chemistry, T.D.M.N.S. College, T. Kallikulam, Tamilnadu, India, and ^eInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: b_ravidurai@yahoo.com

(Received 26 December 2009; accepted 1 January 2010; online 13 January 2010)

There are two monomeric units in the asymmetric unit of the polymeric title compound, [Na(C₅H₄NOS)(C₁₀H₈N₂O₂S₂)(H₂O)]_n. The Na^I ions are six coordinated by four O atoms, one S atom and one water molecule, forming a slightly distorted octahedral geometry. An intramolecular O—H⋯O hydrogen bond stabilizes the conformation of the molecule. The crystal packing is consolidated by intermolecular O—H⋯O, O—H⋯N and O—H⋯S hydrogen bonds, π–π interactions [with centroid–centroid distances of 3.587 (2) Å] together with weak C—H⋯π interactions. The molecules are linked into polymeric chains along the b-axis direction.

Related literature

For the biological activity of N-oxides and their derivatives, see: Lobana & Bhatia (1989 ); Symons et al. (1985 ). For their involvement in DNA strand scission under physiological conditions, see: Katsuyuki et al. (1991 ); Bovin et al. (1992 ). Pyridine N-oxides bearing a sulfur group in position two display significant antimicrobial activity, see: Leonard et al. (1955 ). For related structures, see: Jebas et al. (2005 ); Ravindran et al. (2008 ).

Experimental

Crystal data

[Na(C₅H₄NOS)(C₁₀H₈N₂O₂S₂)(H₂O)]
M_r = 838.92
Orthorhombic, P c a 2₁
a = 24.829 (2) Å
b = 7.3290 (7) Å
c = 19.1378 (17) Å
V = 3482.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 173 K
0.54 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.782, T_max = 0.936
38861 measured reflections
8403 independent reflections
6205 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.074
S = 0.93
8403 reflections
469 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 4068 Friedel pairs
Flack parameter: 0.47 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N34/C33–C35 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O49—H49A⋯O16ⁱ	0.90	1.91	2.784 (3)	165
O49—H49A⋯N11ⁱ	0.90	2.67	3.417 (3)	141
O49—H49B⋯S32ⁱⁱ	0.89	2.37	3.198 (2)	154
O50—H50A⋯O39ⁱⁱⁱ	0.92	1.88	2.798 (3)	177
O50—H50A⋯N34ⁱⁱⁱ	0.92	2.62	3.455 (3)	151
O50—H50B⋯S24	0.86	2.33	3.193 (2)	174
C29—H29⋯Cg1^iv	0.95	2.89	3.618 (4)	134
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+1, z]$ ; (ii) x, y-1, z; (iii) $[x-{\script{1\over 2}}, -y+1, z]$ ; (iv) $[-x+{\script{3\over 2}}, y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810000073/bt5158sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000073/bt5158Isup2.hkl

checkCIF report

Comment top

N-oxides and their derivatives show a broad spectrum of biological activity such as antifungal, antimicrobial and antibacterial activities (Lobana & Bhatia, 1989; Symons et al., 1985). These compounds are also found to be involved in DNA strand scission under physiological conditions (Katsuyuki et al., 1991; Bovin et al., 1992). Pyridine N-oxides bearing a sulfur group in position two display significant antimicrobial activity (Leonard et al., 1955). In view of the importance of N-oxides, we have previously reported the crystal structures of N-oxide derivatives (Jebas et al., 2005; Ravindran et al., 2008). As an extension of our work on N-oxide derivatives, we report here the crystal structure of the title compound (I).

In the asymmetric unit of (I)(Fig 1), the Na^I ion is six coordinated by four oxygen atoms, two from 1-oxypyridine-2-thiolato and two from 2,2-thiobis(pyridine N-oxide) ligands, and one sulfur atom from 1-oxypyridine-2-thiolato ligand. The pyridyl rings are essentially planar with the maximum deviation from planarity of -0.034 (5) Å for atom C10. The N–O bond lengths are in good agreement with the mean value of 1.304 (15) Å reported in the literature for pyridine N-oxides.

Intramolecular O—H···O hydrogen bonding influence the conformation of the molecule. The crystal packing (Fig 2) is consolidated by intermolecular O—H···O, O—H···N and O—H···S hydrogen bonding together with intramolecular S···O= 2.587 (3) to 3.069 (3) Å; N···S=2.686 (4) to 2.700 (5) Å; S···Na=3.807 (2) Å, intermolecular S···Oⁱ=3.065 (3) Å, O···Oⁱ=2.784 (3), O···Oⁱⁱ=2.798 (3) Å, intramolecular S···O =2.587 (3)to 3.069 (3) Å; O···O = 2.784 (3) to 2.798 (3) Å; S···Na=3.807 (2) Å and N···S=2.686 (4) to 2.700 (5) Å short contacts [symmetry code: (i) 1/2+X,1-Y,Z (ii) -1/2+X, 1-Y, Z]. π—π interactions with cg1-cg4ⁱⁱⁱ=3.587 (2)Å (Where Cg1 is N1/C2—C6; Cg2 is N25/C26—C30) [symmetry code: (iii) X, -1+Y, Z] together with weak C—H··· π interactions. The molecules are linked into polymeric chains along the b-direction.

Related literature top

For the biological activity of N-oxides and their derivatives, see: Lobana & Bhatia (1989); Symons et al. (1985). For their involvement in DNA strand scission under physiological conditions, see: Katsuyuki et al. (1991); Bovin et al. (1992). Pyridine N-oxides bearing a sulfur group in position two display significant antimicrobial activity, see: Leonard et al. (1955). For related structures: Jebas et al. (2005); Ravindran et al. (2008).

Experimental top

A mixture of Sodium salt of 1-hydroxypyidine-2-thione (0.298 2mmol), ethanol (10 ml)and sodium ethoxide (10ml) was heated at 333 K with stirring for 30 min. After two days again Sodium salt of 1-hydroxypyidine-2-thione(0.149,1mmol)was added. The solution was again heated at 333 K with stirring for 30 min. The mixture was then kept aside for slow evaporation. After a week colourless crystals were formed.

Structure description top

For the biological activity of N-oxides and their derivatives, see: Lobana & Bhatia (1989); Symons et al. (1985). For their involvement in DNA strand scission under physiological conditions, see: Katsuyuki et al. (1991); Bovin et al. (1992). Pyridine N-oxides bearing a sulfur group in position two display significant antimicrobial activity, see: Leonard et al. (1955). For related structures: Jebas et al. (2005); Ravindran et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, showing polymeric chains along the b-direction.

catena-Poly[[aquasodium]-µ-[2,2'-(disulfanediyl)bis(pyridine N-oxide)]-µ-(pyridine-2-thiolato 1-oxide)] top

Crystal data top

[Na(C₅H₄NOS)(C₁₀H₈N₂O₂S₂)(H₂O)]	F(000) = 1728
M_r = 838.92	D_x = 1.600 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2ac	Cell parameters from 6853 reflections
a = 24.829 (2) Å	θ = 2.7–27.9°
b = 7.3290 (7) Å	µ = 0.48 mm⁻¹
c = 19.1378 (17) Å	T = 173 K
V = 3482.5 (5) Å³	Block, colorless
Z = 4	0.54 × 0.19 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	8403 independent reflections
Radiation source: sealed Tube	6205 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
CCD scan	θ_max = 28.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −32→30
T_min = 0.782, T_max = 0.936	k = −9→9
38861 measured reflections	l = −25→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: calc
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0277P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
8403 reflections	Δρ_max = 0.28 e Å⁻³
469 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 4068 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.47 (6)

Crystal data top

[Na(C₅H₄NOS)(C₁₀H₈N₂O₂S₂)(H₂O)]	V = 3482.5 (5) Å³
M_r = 838.92	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 24.829 (2) Å	µ = 0.48 mm⁻¹
b = 7.3290 (7) Å	T = 173 K
c = 19.1378 (17) Å	0.54 × 0.19 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	8403 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	6205 reflections with I > 2σ(I)
T_min = 0.782, T_max = 0.936	R_int = 0.077
38861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.28 e Å⁻³
S = 0.93	Δρ_min = −0.23 e Å⁻³
8403 reflections	Absolute structure: Flack (1983), 4068 Friedel pairs
469 parameters	Absolute structure parameter: 0.47 (6)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
Na1	0.62174 (8)	0.7233 (3)	0.43117 (11)	0.0209 (4)
Na2	0.63035 (8)	0.2253 (3)	0.42791 (11)	0.0205 (4)
N1	0.55812 (13)	0.4551 (4)	0.55069 (17)	0.0169 (6)
C2	0.5074 (3)	0.5199 (5)	0.5651 (4)	0.0192 (12)
C3	0.4871 (3)	0.5177 (5)	0.6318 (4)	0.0254 (14)
H3	0.4518	0.5612	0.6413	0.031*
C4	0.51902 (17)	0.4511 (5)	0.6844 (2)	0.0284 (8)
H4	0.5059	0.4482	0.7310	0.034*
C5	0.57028 (13)	0.3880 (5)	0.66984 (17)	0.0261 (8)
H5	0.5923	0.3419	0.7064	0.031*
C6	0.58936 (13)	0.3919 (4)	0.60254 (17)	0.0233 (7)
H6	0.6247	0.3498	0.5927	0.028*
O7	0.57443 (13)	0.4583 (4)	0.48528 (17)	0.0221 (6)
S8	0.47870 (3)	0.60118 (11)	0.48539 (5)	0.02044 (17)
S9	0.40763 (3)	0.71334 (11)	0.51954 (5)	0.02278 (18)
C10	0.3632 (2)	0.5278 (6)	0.5114 (3)	0.0194 (10)
N11	0.31067 (11)	0.5830 (4)	0.50875 (14)	0.0217 (6)
C12	0.27083 (19)	0.4613 (6)	0.4983 (3)	0.0257 (10)
H12	0.2348	0.5032	0.4931	0.031*
C13	0.28145 (15)	0.2766 (6)	0.49496 (19)	0.0247 (9)
H13	0.2530	0.1922	0.4873	0.030*
C14	0.33365 (14)	0.2158 (5)	0.50285 (17)	0.0245 (8)
H14	0.3414	0.0889	0.5026	0.029*
C15	0.37491 (14)	0.3433 (5)	0.51114 (17)	0.0208 (7)
H15	0.4111	0.3034	0.5166	0.025*
O16	0.30158 (11)	0.7595 (4)	0.51612 (17)	0.0334 (7)
N17	0.68938 (18)	0.4697 (4)	0.3143 (2)	0.0169 (8)
C18	0.65984 (13)	0.3867 (4)	0.26226 (16)	0.0202 (7)
C19	0.68407 (14)	0.3771 (5)	0.19601 (17)	0.0263 (8)
H19	0.6645	0.3237	0.1585	0.032*
C20	0.73511 (18)	0.4424 (6)	0.1836 (2)	0.0320 (9)
H20	0.7508	0.4317	0.1385	0.038*
C21	0.7630 (2)	0.5230 (5)	0.2370 (3)	0.0292 (13)
H21	0.7981	0.5705	0.2288	0.035*
C22	0.7405 (2)	0.5353 (5)	0.3019 (3)	0.0234 (10)
H22	0.7603	0.5895	0.3390	0.028*
O23	0.67089 (18)	0.4834 (3)	0.3798 (3)	0.0219 (9)
S24	0.59697 (3)	0.30128 (11)	0.28014 (5)	0.02486 (19)
N25	0.5601 (2)	0.9741 (4)	0.5395 (3)	0.0210 (9)
C26	0.51021 (18)	1.0416 (6)	0.5488 (2)	0.0223 (9)
H26	0.4923	1.0962	0.5103	0.027*
C27	0.4846 (2)	1.0345 (6)	0.6115 (3)	0.0295 (11)
H27	0.4490	1.0807	0.6166	0.035*
C28	0.5116 (2)	0.9575 (6)	0.6683 (2)	0.0347 (10)
H28	0.4948	0.9502	0.7128	0.042*
C29	0.56242 (15)	0.8933 (5)	0.65881 (19)	0.0320 (8)
H29	0.5810	0.8448	0.6980	0.038*
C30	0.58885 (13)	0.8950 (4)	0.59367 (17)	0.0230 (7)
O31	0.58128 (18)	0.9846 (3)	0.4763 (2)	0.0212 (9)
S32	0.65125 (3)	0.80270 (12)	0.57957 (5)	0.0296 (2)
C33	0.8877 (2)	0.0209 (5)	0.3402 (3)	0.0169 (10)
N34	0.93985 (10)	0.0766 (4)	0.34558 (13)	0.0190 (6)
C35	0.97985 (18)	−0.0463 (6)	0.3550 (2)	0.0258 (9)
H35	1.0159	−0.0058	0.3612	0.031*
C36	0.96829 (16)	−0.2304 (6)	0.3558 (2)	0.0292 (10)
H36	0.9966	−0.3161	0.3620	0.035*
C37	0.91595 (14)	−0.2915 (5)	0.34758 (18)	0.0269 (8)
H37	0.9080	−0.4183	0.3469	0.032*
C38	0.87541 (14)	−0.1622 (5)	0.34031 (18)	0.0233 (7)
H38	0.8390	−0.2004	0.3354	0.028*
O39	0.94960 (10)	0.2526 (4)	0.33994 (15)	0.0264 (6)
S40	0.84312 (3)	0.20813 (11)	0.33478 (5)	0.02221 (17)
S41	0.77227 (3)	0.09806 (11)	0.37045 (5)	0.01945 (17)
C42	0.7423 (3)	0.0149 (4)	0.2941 (4)	0.0157 (12)
N43	0.69222 (13)	−0.0467 (4)	0.30792 (17)	0.0180 (7)
C44	0.65899 (13)	−0.1106 (4)	0.25716 (17)	0.0219 (7)
H44	0.6236	−0.1497	0.2684	0.026*
C45	0.67693 (13)	−0.1180 (5)	0.18980 (18)	0.0271 (8)
H45	0.6539	−0.1613	0.1538	0.033*
C46	0.72926 (16)	−0.0620 (5)	0.17386 (19)	0.0265 (8)
H46	0.7423	−0.0700	0.1273	0.032*
C47	0.7618 (3)	0.0052 (4)	0.2263 (4)	0.0214 (14)
H47	0.7974	0.0445	0.2161	0.026*
O48	0.67633 (12)	−0.0393 (3)	0.37434 (17)	0.0203 (6)
O49	0.69056 (8)	0.1936 (3)	0.52554 (13)	0.0271 (5)
H49A	0.7262	0.1920	0.5174	0.041*
H49B	0.6880	0.0728	0.5310	0.041*
O50	0.56110 (8)	0.6934 (3)	0.33598 (13)	0.0257 (5)
H50A	0.5244	0.7115	0.3356	0.039*
H50B	0.5700	0.5839	0.3239	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0196 (7)	0.0196 (11)	0.0234 (7)	0.0009 (7)	0.0026 (5)	−0.0003 (7)
Na2	0.0203 (8)	0.0189 (10)	0.0223 (6)	−0.0018 (7)	0.0016 (6)	0.0016 (7)
N1	0.0154 (16)	0.0172 (12)	0.0182 (17)	0.0009 (15)	0.0026 (12)	0.0005 (15)
C2	0.015 (3)	0.0152 (18)	0.027 (3)	−0.0043 (15)	−0.002 (2)	−0.0050 (16)
C3	0.022 (3)	0.026 (2)	0.028 (3)	0.0014 (16)	0.005 (3)	−0.0027 (16)
C4	0.034 (2)	0.034 (2)	0.0177 (19)	−0.003 (2)	0.0063 (17)	−0.0016 (18)
C5	0.0275 (18)	0.0252 (17)	0.0256 (19)	−0.0014 (15)	−0.0027 (15)	0.0018 (15)
C6	0.0184 (16)	0.0214 (16)	0.0300 (19)	0.0002 (14)	−0.0039 (15)	−0.0012 (15)
O7	0.0259 (15)	0.0232 (11)	0.0173 (14)	0.0010 (14)	0.0057 (12)	0.0016 (14)
S8	0.0167 (4)	0.0223 (4)	0.0223 (4)	−0.0001 (3)	0.0008 (3)	−0.0001 (4)
S9	0.0176 (4)	0.0174 (4)	0.0334 (5)	0.0008 (3)	−0.0010 (4)	−0.0023 (4)
C10	0.020 (2)	0.0223 (17)	0.015 (2)	−0.0022 (17)	0.0002 (18)	0.0049 (17)
N11	0.0185 (15)	0.0199 (15)	0.0268 (17)	0.0000 (12)	−0.0002 (12)	−0.0030 (13)
C12	0.017 (2)	0.0306 (18)	0.030 (3)	0.003 (2)	−0.0022 (17)	−0.005 (2)
C13	0.025 (2)	0.029 (2)	0.020 (2)	−0.0078 (17)	−0.0006 (15)	−0.0038 (17)
C14	0.0280 (19)	0.0205 (17)	0.025 (2)	0.0015 (15)	0.0032 (15)	−0.0023 (14)
C15	0.0201 (17)	0.0221 (18)	0.0203 (18)	0.0025 (14)	−0.0007 (15)	0.0015 (14)
O16	0.0310 (17)	0.0227 (14)	0.0466 (18)	0.0028 (13)	0.0001 (15)	−0.0032 (13)
N17	0.017 (2)	0.0170 (13)	0.0162 (19)	0.0016 (14)	0.0036 (15)	0.0023 (15)
C18	0.0254 (17)	0.0142 (15)	0.0211 (18)	0.0072 (14)	−0.0027 (14)	0.0027 (13)
C19	0.036 (2)	0.0246 (17)	0.0183 (19)	0.0091 (16)	0.0015 (15)	0.0015 (14)
C20	0.040 (3)	0.034 (2)	0.023 (2)	0.012 (2)	0.0086 (18)	0.007 (2)
C21	0.025 (3)	0.028 (2)	0.035 (3)	0.0056 (17)	0.010 (2)	0.0114 (19)
C22	0.024 (2)	0.0194 (15)	0.026 (2)	−0.0023 (19)	0.0003 (17)	0.0041 (18)
O23	0.023 (2)	0.0225 (15)	0.020 (2)	−0.0003 (10)	0.0026 (16)	0.0006 (11)
S24	0.0188 (4)	0.0237 (4)	0.0321 (5)	0.0009 (3)	−0.0039 (4)	−0.0021 (4)
N25	0.022 (2)	0.0149 (13)	0.026 (2)	−0.0064 (14)	−0.0042 (16)	−0.0020 (15)
C26	0.014 (2)	0.0229 (16)	0.030 (2)	−0.0051 (19)	0.0006 (16)	−0.0032 (19)
C27	0.023 (2)	0.0294 (19)	0.036 (3)	0.001 (2)	0.004 (2)	−0.005 (2)
C28	0.039 (3)	0.039 (2)	0.025 (2)	−0.012 (2)	0.0154 (19)	−0.003 (2)
C29	0.044 (2)	0.0296 (18)	0.0219 (19)	−0.0083 (17)	−0.0064 (17)	0.0028 (16)
C30	0.0276 (18)	0.0170 (15)	0.0245 (19)	−0.0078 (14)	−0.0031 (15)	0.0011 (14)
O31	0.027 (2)	0.0212 (15)	0.0157 (19)	−0.0011 (10)	0.0056 (16)	0.0035 (10)
S32	0.0226 (5)	0.0258 (4)	0.0404 (5)	−0.0033 (4)	−0.0080 (4)	0.0061 (4)
C33	0.013 (2)	0.0204 (19)	0.018 (2)	−0.0027 (14)	0.0012 (18)	0.0048 (16)
N34	0.0184 (15)	0.0208 (15)	0.0177 (15)	−0.0004 (11)	0.0012 (12)	0.0011 (12)
C35	0.016 (2)	0.0321 (19)	0.029 (3)	0.006 (2)	0.0015 (17)	0.005 (2)
C36	0.028 (2)	0.025 (2)	0.034 (2)	0.0109 (17)	0.0112 (17)	0.0102 (17)
C37	0.0299 (19)	0.0197 (17)	0.031 (2)	0.0030 (16)	0.0082 (16)	0.0029 (15)
C38	0.0214 (18)	0.0237 (18)	0.0247 (19)	−0.0026 (14)	0.0021 (16)	0.0014 (15)
O39	0.0208 (14)	0.0211 (14)	0.0372 (16)	−0.0042 (11)	−0.0021 (13)	0.0015 (11)
S40	0.0160 (4)	0.0168 (4)	0.0338 (5)	−0.0014 (3)	−0.0001 (4)	0.0036 (4)
S41	0.0157 (4)	0.0201 (4)	0.0226 (4)	−0.0007 (3)	0.0008 (3)	0.0012 (4)
C42	0.017 (3)	0.0138 (18)	0.017 (3)	0.0040 (13)	0.002 (2)	−0.0006 (13)
N43	0.0181 (16)	0.0150 (12)	0.0211 (17)	0.0051 (15)	0.0019 (13)	−0.0011 (15)
C44	0.0158 (16)	0.0209 (16)	0.0291 (19)	−0.0009 (14)	0.0009 (14)	−0.0031 (14)
C45	0.0243 (18)	0.0305 (19)	0.026 (2)	0.0017 (15)	−0.0063 (15)	−0.0036 (16)
C46	0.034 (2)	0.0272 (18)	0.0185 (19)	0.004 (2)	0.0053 (16)	−0.0049 (17)
C47	0.019 (3)	0.024 (3)	0.021 (3)	0.0018 (12)	0.005 (2)	0.0008 (13)
O48	0.0208 (14)	0.0218 (10)	0.0183 (15)	−0.0017 (13)	0.0060 (11)	0.0025 (14)
O49	0.0188 (11)	0.0225 (12)	0.0399 (14)	0.0010 (10)	0.0010 (10)	0.0065 (11)
O50	0.0181 (11)	0.0247 (12)	0.0343 (13)	0.0037 (10)	−0.0003 (10)	−0.0038 (11)

Geometric parameters (Å, º) top

Na1—O31	2.328 (4)	C21—C22	1.366 (8)
Na1—O23	2.355 (4)	C21—H21	0.9500
Na1—O50	2.373 (3)	C22—H22	0.9500
Na1—O48ⁱ	2.459 (3)	N25—O31	1.321 (7)
Na1—O7	2.495 (3)	N25—C26	1.345 (6)
Na1—S32	2.990 (3)	N25—C30	1.387 (6)
Na1—H50B	2.6283	C26—C27	1.360 (7)
Na2—O23	2.332 (4)	C26—H26	0.9500
Na2—O31ⁱⁱ	2.335 (4)	C27—C28	1.397 (7)
Na2—O49	2.404 (3)	C27—H27	0.9500
Na2—O7	2.459 (3)	C28—C29	1.358 (6)
Na2—O48	2.473 (3)	C28—H28	0.9500
Na2—S24	2.999 (2)	C29—C30	1.409 (5)
N1—O7	1.316 (4)	C29—H29	0.9500
N1—C6	1.342 (4)	C30—S32	1.712 (4)
N1—C2	1.374 (7)	O31—Na2ⁱ	2.335 (4)
C2—C3	1.372 (10)	C33—N34	1.362 (6)
C2—S8	1.785 (7)	C33—C38	1.377 (4)
C3—C4	1.371 (8)	C33—S40	1.766 (5)
C3—H3	0.9500	N34—O39	1.317 (4)
C4—C5	1.382 (5)	N34—C35	1.353 (5)
C4—H4	0.9500	C35—C36	1.380 (6)
C5—C6	1.373 (4)	C35—H35	0.9500
C5—H5	0.9500	C36—C37	1.384 (5)
C6—H6	0.9500	C36—H36	0.9500
S8—S9	2.0536 (11)	C37—C38	1.389 (5)
S9—C10	1.758 (5)	C37—H37	0.9500
C10—N11	1.367 (6)	C38—H38	0.9500
C10—C15	1.383 (5)	S40—S41	2.0521 (11)
N11—O16	1.320 (4)	S41—C42	1.750 (7)
N11—C12	1.347 (5)	C42—N43	1.348 (7)
C12—C13	1.380 (6)	C42—C47	1.386 (10)
C12—H12	0.9500	N43—O48	1.332 (4)
C13—C14	1.379 (5)	N43—C44	1.358 (4)
C13—H13	0.9500	C44—C45	1.365 (4)
C14—C15	1.396 (5)	C44—H44	0.9500
C14—H14	0.9500	C45—C46	1.396 (5)
C15—H15	0.9500	C45—H45	0.9500
N17—O23	1.339 (7)	C46—C47	1.380 (8)
N17—C22	1.378 (6)	C46—H46	0.9500
N17—C18	1.378 (5)	C47—H47	0.9500
C18—C19	1.405 (4)	O48—Na1ⁱⁱ	2.459 (3)
C18—S24	1.716 (3)	O49—H49A	0.8987
C19—C20	1.375 (6)	O49—H49B	0.8936
C19—H19	0.9500	O50—H50A	0.9220
C20—C21	1.368 (7)	O50—H50B	0.8634
C20—H20	0.9500

O31—Na1—O23	172.9 (2)	C12—C13—H13	120.3
O31—Na1—O50	94.98 (15)	C13—C14—C15	119.1 (3)
O23—Na1—O50	86.52 (14)	C13—C14—H14	120.5
O31—Na1—O48ⁱ	79.63 (13)	C15—C14—H14	120.5
O23—Na1—O48ⁱ	93.33 (13)	C10—C15—C14	120.0 (4)
O50—Na1—O48ⁱ	94.33 (12)	C10—C15—H15	120.0
O31—Na1—O7	106.45 (14)	C14—C15—H15	120.0
O23—Na1—O7	80.56 (13)	O23—N17—C22	116.8 (4)
O50—Na1—O7	87.02 (11)	O23—N17—C18	121.8 (4)
O48ⁱ—Na1—O7	173.66 (15)	C22—N17—C18	121.4 (4)
O31—Na1—S32	66.01 (13)	N17—C18—C19	116.5 (3)
O23—Na1—S32	114.50 (14)	N17—C18—S24	120.1 (3)
O50—Na1—S32	154.47 (11)	C19—C18—S24	123.4 (3)
O48ⁱ—Na1—S32	98.48 (10)	C20—C19—C18	122.2 (3)
O7—Na1—S32	82.68 (10)	C20—C19—H19	118.9
O31—Na1—Na2	148.47 (11)	C18—C19—H19	118.9
O23—Na1—Na2	38.50 (10)	C21—C20—C19	119.2 (4)
O50—Na1—Na2	86.09 (7)	C21—C20—H20	120.4
O48ⁱ—Na1—Na2	131.80 (9)	C19—C20—H20	120.4
O7—Na1—Na2	42.06 (9)	C22—C21—C20	120.0 (5)
S32—Na1—Na2	101.31 (5)	C22—C21—H21	120.0
O31—Na1—Na2ⁱ	37.85 (11)	C20—C21—H21	120.0
O23—Na1—Na2ⁱ	135.08 (11)	C21—C22—N17	120.7 (5)
O50—Na1—Na2ⁱ	96.66 (7)	C21—C22—H22	119.7
O48ⁱ—Na1—Na2ⁱ	41.79 (8)	N17—C22—H22	119.7
O7—Na1—Na2ⁱ	144.23 (9)	N17—O23—Na2	117.2 (2)
S32—Na1—Na2ⁱ	78.91 (4)	N17—O23—Na1	128.6 (3)
Na2—Na1—Na2ⁱ	173.05 (4)	Na2—O23—Na1	102.53 (19)
O31—Na1—H50B	113.5	C18—S24—Na2	90.25 (11)
O23—Na1—H50B	68.7	O31—N25—C26	117.9 (4)
O50—Na1—H50B	19.0	O31—N25—C30	120.2 (4)
O48ⁱ—Na1—H50B	101.5	C26—N25—C30	121.9 (5)
O7—Na1—H50B	77.9	N25—C26—C27	122.3 (5)
S32—Na1—H50B	159.6	N25—C26—H26	118.9
Na2—Na1—H50B	68.1	C27—C26—H26	118.9
Na2ⁱ—Na1—H50B	113.8	C26—C27—C28	118.5 (5)
O23—Na2—O31ⁱⁱ	173.9 (2)	C26—C27—H27	120.8
O23—Na2—O49	96.71 (16)	C28—C27—H27	120.8
O31ⁱⁱ—Na2—O49	86.74 (14)	C29—C28—C27	118.8 (4)
O23—Na2—O7	81.77 (13)	C29—C28—H28	120.6
O31ⁱⁱ—Na2—O7	93.04 (13)	C27—C28—H28	120.6
O49—Na2—O7	94.09 (12)	C28—C29—C30	123.2 (4)
O23—Na2—O48	105.84 (14)	C28—C29—H29	118.4
O31ⁱⁱ—Na2—O48	79.21 (13)	C30—C29—H29	118.4
O49—Na2—O48	87.67 (11)	N25—C30—C29	115.2 (3)
O7—Na2—O48	171.96 (15)	N25—C30—S32	120.9 (3)
O23—Na2—S24	66.19 (13)	C29—C30—S32	123.9 (3)
O31ⁱⁱ—Na2—S24	111.71 (14)	N25—O31—Na1	117.6 (2)
O49—Na2—S24	157.31 (10)	N25—O31—Na2ⁱ	127.9 (2)
O7—Na2—S24	97.82 (10)	Na1—O31—Na2ⁱ	104.43 (19)
O48—Na2—S24	83.23 (10)	C30—S32—Na1	90.28 (12)
O23—Na2—Na1	38.96 (11)	N34—C33—C38	120.2 (4)
O31ⁱⁱ—Na2—Na1	135.80 (10)	N34—C33—S40	111.6 (3)
O49—Na2—Na1	96.87 (8)	C38—C33—S40	128.2 (4)
O7—Na2—Na1	42.81 (8)	O39—N34—C35	121.9 (3)
O48—Na2—Na1	144.76 (9)	O39—N34—C33	117.5 (3)
S24—Na2—Na1	79.32 (4)	C35—N34—C33	120.6 (3)
O23—Na2—Na1ⁱⁱ	147.27 (11)	N34—C35—C36	120.0 (4)
O31ⁱⁱ—Na2—Na1ⁱⁱ	37.72 (10)	N34—C35—H35	120.0
O49—Na2—Na1ⁱⁱ	85.78 (7)	C36—C35—H35	120.0
O7—Na2—Na1ⁱⁱ	130.75 (9)	C35—C36—C37	120.7 (4)
O48—Na2—Na1ⁱⁱ	41.50 (8)	C35—C36—H36	119.6
S24—Na2—Na1ⁱⁱ	100.67 (5)	C37—C36—H36	119.6
Na1—Na2—Na1ⁱⁱ	173.05 (4)	C36—C37—C38	118.1 (4)
O7—N1—C6	122.1 (3)	C36—C37—H37	121.0
O7—N1—C2	117.8 (4)	C38—C37—H37	121.0
C6—N1—C2	120.1 (4)	C33—C38—C37	120.3 (4)
C3—C2—N1	121.2 (5)	C33—C38—H38	119.8
C3—C2—S8	130.7 (5)	C37—C38—H38	119.8
N1—C2—S8	108.0 (4)	C33—S40—S41	102.27 (16)
C4—C3—C2	118.4 (5)	C42—S41—S40	102.9 (2)
C4—C3—H3	120.8	N43—C42—C47	119.3 (5)
C2—C3—H3	120.8	N43—C42—S41	110.1 (4)
C3—C4—C5	120.2 (4)	C47—C42—S41	130.5 (5)
C3—C4—H4	119.9	O48—N43—C42	116.6 (4)
C5—C4—H4	119.9	O48—N43—C44	121.1 (3)
C6—C5—C4	120.0 (3)	C42—N43—C44	122.3 (4)
C6—C5—H5	120.0	N43—C44—C45	119.4 (3)
C4—C5—H5	120.0	N43—C44—H44	120.3
N1—C6—C5	120.1 (3)	C45—C44—H44	120.3
N1—C6—H6	119.9	C44—C45—C46	119.9 (3)
C5—C6—H6	119.9	C44—C45—H45	120.1
N1—O7—Na2	125.9 (2)	C46—C45—H45	120.1
N1—O7—Na1	123.6 (2)	C47—C46—C45	119.4 (4)
Na2—O7—Na1	95.13 (14)	C47—C46—H46	120.3
C2—S8—S9	101.8 (2)	C45—C46—H46	120.3
C10—S9—S8	101.62 (18)	C46—C47—C42	119.6 (5)
N11—C10—C15	119.3 (4)	C46—C47—H47	120.2
N11—C10—S9	111.9 (3)	C42—C47—H47	120.2
C15—C10—S9	128.7 (4)	N43—O48—Na1ⁱⁱ	123.8 (2)
O16—N11—C12	122.6 (3)	N43—O48—Na2	124.4 (2)
O16—N11—C10	116.7 (3)	Na1ⁱⁱ—O48—Na2	96.72 (14)
C12—N11—C10	120.7 (3)	Na2—O49—H49A	118.6
N11—C12—C13	121.1 (4)	Na2—O49—H49B	98.2
N11—C12—H12	119.5	H49A—O49—H49B	94.4
C13—C12—H12	119.5	Na1—O50—H50A	128.3
C14—C13—C12	119.4 (4)	Na1—O50—H50B	97.4
C14—C13—H13	120.3	H50A—O50—H50B	112.6

O31—Na1—Na2—O23	−177.5 (4)	S24—Na2—O23—N17	−43.5 (3)
O50—Na1—Na2—O23	89.3 (2)	Na1—Na2—O23—N17	−146.4 (5)
O48ⁱ—Na1—Na2—O23	−3.0 (2)	Na1ⁱⁱ—Na2—O23—N17	28.3 (5)
O7—Na1—Na2—O23	179.2 (3)	O49—Na2—O23—Na1	−92.64 (17)
S32—Na1—Na2—O23	−115.3 (2)	O7—Na2—O23—Na1	0.54 (18)
O31—Na1—Na2—O31ⁱⁱ	7.08 (14)	O48—Na2—O23—Na1	177.89 (15)
O23—Na1—Na2—O31ⁱⁱ	−175.4 (4)	S24—Na2—O23—Na1	102.91 (17)
O50—Na1—Na2—O31ⁱⁱ	−86.1 (2)	Na1ⁱⁱ—Na2—O23—Na1	174.73 (9)
O48ⁱ—Na1—Na2—O31ⁱⁱ	−178.4 (2)	O50—Na1—O23—N17	52.9 (4)
O7—Na1—Na2—O31ⁱⁱ	3.8 (2)	O48ⁱ—Na1—O23—N17	−41.2 (4)
S32—Na1—Na2—O31ⁱⁱ	69.24 (19)	O7—Na1—O23—N17	140.5 (4)
O31—Na1—Na2—O49	−85.3 (3)	S32—Na1—O23—N17	−142.1 (4)
O23—Na1—Na2—O49	92.2 (2)	Na2—Na1—O23—N17	141.0 (5)
O50—Na1—Na2—O49	−178.48 (13)	Na2ⁱ—Na1—O23—N17	−43.0 (5)
O48ⁱ—Na1—Na2—O49	89.20 (15)	O50—Na1—O23—Na2	−88.09 (17)
O7—Na1—Na2—O49	−88.60 (15)	O48ⁱ—Na1—O23—Na2	177.77 (17)
S32—Na1—Na2—O49	−23.15 (7)	O7—Na1—O23—Na2	−0.54 (18)
O31—Na1—Na2—O7	3.3 (3)	S32—Na1—O23—Na2	76.89 (19)
O23—Na1—Na2—O7	−179.2 (3)	Na2ⁱ—Na1—O23—Na2	175.96 (7)
O50—Na1—Na2—O7	−89.89 (15)	N17—C18—S24—Na2	−30.1 (3)
O48ⁱ—Na1—Na2—O7	177.8 (3)	C19—C18—S24—Na2	149.7 (3)
S32—Na1—Na2—O7	65.44 (13)	O23—Na2—S24—C18	33.22 (15)
O31—Na1—Na2—O48	179.0 (3)	O31ⁱⁱ—Na2—S24—C18	−152.94 (15)
O23—Na1—Na2—O48	−3.5 (2)	O49—Na2—S24—C18	−10.4 (3)
O50—Na1—Na2—O48	85.81 (18)	O7—Na2—S24—C18	110.60 (14)
O48ⁱ—Na1—Na2—O48	−6.51 (11)	O48—Na2—S24—C18	−77.44 (13)
O7—Na1—Na2—O48	175.7 (3)	Na1—Na2—S24—C18	71.81 (11)
S32—Na1—Na2—O48	−118.86 (18)	Na1ⁱⁱ—Na2—S24—C18	−115.26 (11)
O31—Na1—Na2—S24	117.3 (3)	O31—N25—C26—C27	178.8 (4)
O23—Na1—Na2—S24	−65.2 (2)	C30—N25—C26—C27	−0.9 (6)
O50—Na1—Na2—S24	24.16 (7)	N25—C26—C27—C28	1.4 (7)
O48ⁱ—Na1—Na2—S24	−68.16 (13)	C26—C27—C28—C29	0.1 (7)
O7—Na1—Na2—S24	114.04 (15)	C27—C28—C29—C30	−2.1 (6)
S32—Na1—Na2—S24	179.49 (8)	O31—N25—C30—C29	179.3 (3)
O7—N1—C2—C3	178.7 (4)	C26—N25—C30—C29	−0.9 (5)
C6—N1—C2—C3	−1.6 (6)	O31—N25—C30—S32	−2.2 (5)
O7—N1—C2—S8	−2.2 (4)	C26—N25—C30—S32	177.6 (3)
C6—N1—C2—S8	177.5 (3)	C28—C29—C30—N25	2.4 (5)
N1—C2—C3—C4	0.8 (6)	C28—C29—C30—S32	−176.0 (3)
S8—C2—C3—C4	−178.0 (3)	C26—N25—O31—Na1	−132.8 (3)
C2—C3—C4—C5	−0.1 (6)	C30—N25—O31—Na1	47.0 (5)
C3—C4—C5—C6	0.0 (6)	C26—N25—O31—Na2ⁱ	87.3 (5)
O7—N1—C6—C5	−178.8 (3)	C30—N25—O31—Na2ⁱ	−92.9 (4)
C2—N1—C6—C5	1.5 (5)	O50—Na1—O31—N25	117.2 (4)
C4—C5—C6—N1	−0.7 (5)	O48ⁱ—Na1—O31—N25	−149.3 (4)
C6—N1—O7—Na2	37.1 (5)	O7—Na1—O31—N25	28.9 (4)
C2—N1—O7—Na2	−143.2 (3)	S32—Na1—O31—N25	−45.1 (3)
C6—N1—O7—Na1	−90.7 (4)	Na2—Na1—O31—N25	26.6 (5)
C2—N1—O7—Na1	89.0 (4)	Na2ⁱ—Na1—O31—N25	−148.3 (5)
O23—Na2—O7—N1	−139.2 (3)	O50—Na1—O31—Na2ⁱ	−94.44 (18)
O31ⁱⁱ—Na2—O7—N1	44.0 (3)	O48ⁱ—Na1—O31—Na2ⁱ	−0.94 (18)
O49—Na2—O7—N1	−43.0 (3)	O7—Na1—O31—Na2ⁱ	177.20 (15)
S24—Na2—O7—N1	156.4 (3)	S32—Na1—O31—Na2ⁱ	103.27 (18)
Na1—Na2—O7—N1	−138.7 (3)	Na2—Na1—O31—Na2ⁱ	174.91 (10)
Na1ⁱⁱ—Na2—O7—N1	45.0 (3)	N25—C30—S32—Na1	−28.0 (3)
O23—Na2—O7—Na1	−0.50 (16)	C29—C30—S32—Na1	150.4 (3)
O31ⁱⁱ—Na2—O7—Na1	−177.35 (15)	O31—Na1—S32—C30	32.34 (16)
O49—Na2—O7—Na1	95.70 (12)	O23—Na1—S32—C30	−155.44 (16)
S24—Na2—O7—Na1	−64.94 (12)	O50—Na1—S32—C30	−12.3 (2)
Na1ⁱⁱ—Na2—O7—Na1	−176.35 (6)	O48ⁱ—Na1—S32—C30	106.95 (14)
O31—Na1—O7—N1	−38.2 (3)	O7—Na1—S32—C30	−79.35 (13)
O23—Na1—O7—N1	140.5 (3)	Na2—Na1—S32—C30	−117.25 (11)
O50—Na1—O7—N1	−132.5 (3)	Na2ⁱ—Na1—S32—C30	69.83 (11)
S32—Na1—O7—N1	24.1 (3)	C38—C33—N34—O39	175.1 (4)
Na2—Na1—O7—N1	140.0 (3)	S40—C33—N34—O39	−5.8 (5)
Na2ⁱ—Na1—O7—N1	−35.2 (4)	C38—C33—N34—C35	−3.7 (7)
O31—Na1—O7—Na2	−178.21 (15)	S40—C33—N34—C35	175.5 (3)
O23—Na1—O7—Na2	0.50 (16)	O39—N34—C35—C36	−175.5 (4)
O50—Na1—O7—Na2	87.46 (13)	C33—N34—C35—C36	3.2 (6)
S32—Na1—O7—Na2	−115.94 (10)	N34—C35—C36—C37	−0.6 (6)
Na2ⁱ—Na1—O7—Na2	−175.27 (8)	C35—C36—C37—C38	−1.6 (6)
C3—C2—S8—S9	4.4 (4)	N34—C33—C38—C37	1.4 (7)
N1—C2—S8—S9	−174.6 (2)	S40—C33—C38—C37	−177.6 (4)
C2—S8—S9—C10	−91.6 (2)	C36—C37—C38—C33	1.1 (6)
S8—S9—C10—N11	−159.6 (3)	N34—C33—S40—S41	−155.9 (3)
S8—S9—C10—C15	24.0 (5)	C38—C33—S40—S41	23.2 (5)
C15—C10—N11—O16	173.5 (4)	C33—S40—S41—C42	−89.8 (2)
S9—C10—N11—O16	−3.3 (5)	S40—S41—C42—N43	−173.9 (2)
C15—C10—N11—C12	−7.2 (7)	S40—S41—C42—C47	5.9 (4)
S9—C10—N11—C12	176.0 (3)	C47—C42—N43—O48	177.9 (3)
O16—N11—C12—C13	−176.1 (4)	S41—C42—N43—O48	−2.2 (4)
C10—N11—C12—C13	4.7 (7)	C47—C42—N43—C44	−3.2 (5)
N11—C12—C13—C14	0.4 (6)	S41—C42—N43—C44	176.7 (3)
C12—C13—C14—C15	−2.7 (5)	O48—N43—C44—C45	−179.3 (3)
N11—C10—C15—C14	4.9 (7)	C42—N43—C44—C45	1.8 (5)
S9—C10—C15—C14	−178.9 (4)	N43—C44—C45—C46	0.7 (5)
C13—C14—C15—C10	0.0 (5)	C44—C45—C46—C47	−1.8 (5)
O23—N17—C18—C19	−178.6 (3)	C45—C46—C47—C42	0.4 (6)
C22—N17—C18—C19	−1.6 (5)	N43—C42—C47—C46	2.0 (5)
O23—N17—C18—S24	1.3 (5)	S41—C42—C47—C46	−177.9 (3)
C22—N17—C18—S24	178.3 (3)	C42—N43—O48—Na1ⁱⁱ	−141.7 (3)
N17—C18—C19—C20	1.6 (5)	C44—N43—O48—Na1ⁱⁱ	39.4 (4)
S24—C18—C19—C20	−178.2 (3)	C42—N43—O48—Na2	89.4 (4)
C18—C19—C20—C21	−1.4 (6)	C44—N43—O48—Na2	−89.6 (4)
C19—C20—C21—C22	1.0 (6)	O23—Na2—O48—N43	−38.0 (3)
C20—C21—C22—N17	−1.0 (6)	O31ⁱⁱ—Na2—O48—N43	138.5 (3)
O23—N17—C22—C21	178.5 (4)	O49—Na2—O48—N43	−134.3 (3)
C18—N17—C22—C21	1.4 (6)	S24—Na2—O48—N43	24.8 (3)
C22—N17—O23—Na2	−133.1 (3)	Na1—Na2—O48—N43	−35.7 (4)
C18—N17—O23—Na2	44.0 (5)	Na1ⁱⁱ—Na2—O48—N43	139.4 (3)
C22—N17—O23—Na1	90.6 (5)	O23—Na2—O48—Na1ⁱⁱ	−177.42 (15)
C18—N17—O23—Na1	−92.3 (4)	O31ⁱⁱ—Na2—O48—Na1ⁱⁱ	−0.86 (16)
O49—Na2—O23—N17	120.9 (3)	O49—Na2—O48—Na1ⁱⁱ	86.26 (13)
O7—Na2—O23—N17	−145.9 (4)	S24—Na2—O48—Na1ⁱⁱ	−114.56 (11)
O48—Na2—O23—N17	31.4 (4)	Na1—Na2—O48—Na1ⁱⁱ	−175.12 (8)

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

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the N34/C33–C35 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O49—H49A···O16ⁱⁱⁱ	0.90	1.91	2.784 (3)	165
O49—H49A···N11ⁱⁱⁱ	0.90	2.67	3.417 (3)	141
O49—H49B···S32ⁱⁱ	0.89	2.37	3.198 (2)	154
O50—H50A···O39^iv	0.92	1.88	2.798 (3)	177
O50—H50A···N34^iv	0.92	2.62	3.455 (3)	151
O50—H50B···S24	0.86	2.33	3.193 (2)	174
C29—H29···Cg1^v	0.95	2.89	3.618 (4)	134

Symmetry codes: (ii) x, y−1, z; (iii) x+1/2, −y+1, z; (iv) x−1/2, −y+1, z; (v) −x+3/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Na(C₅H₄NOS)(C₁₀H₈N₂O₂S₂)(H₂O)]
M_r	838.92
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	24.829 (2), 7.3290 (7), 19.1378 (17)
V (Å³)	3482.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.54 × 0.19 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.782, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	38861, 8403, 6205
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.074, 0.93
No. of reflections	8403
No. of parameters	469
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.23
Absolute structure	Flack (1983), 4068 Friedel pairs
Absolute structure parameter	0.47 (6)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the N34/C33–C35 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O49—H49A···O16ⁱ	0.90	1.91	2.784 (3)	165
O49—H49A···N11ⁱ	0.90	2.67	3.417 (3)	141
O49—H49B···S32ⁱⁱ	0.89	2.37	3.198 (2)	154
O50—H50A···O39ⁱⁱⁱ	0.92	1.88	2.798 (3)	177
O50—H50A···N34ⁱⁱⁱ	0.92	2.62	3.455 (3)	151
O50—H50B···S24	0.86	2.33	3.193 (2)	174
C29—H29···Cg1^iv	0.95	2.89	3.618 (4)	134

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x, y−1, z; (iii) x−1/2, −y+1, z; (iv) −x+3/2, y+1, z+1/2.

References

Bovin, D. H. R., Crepon, E. & Zard, S. Z. (1992). Bull. Soc. Chim. Fr. 129, 145–150. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jebas, S. R., Balasubramanian, T., Ravidurai, B. & Kumaresan, S. (2005). Acta Cryst. E61, o2677–o2678. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katsuyuki, N., Carter, B. J., Xu, J. & Hetch, S. M. (1991). J. Am. Chem. Soc. 113, 5099–5100. Google Scholar
Leonard, F., Barklay, F. A., Brown, E. V., Anderson, F. E. & Green, D. M. (1955). Antibiot. Chemother. pp. 261–264. Google Scholar
Lobana, T. S. & Bhatia, P. K. (1989). J. Sci. Ind. Res. 48, 394–401. CAS Google Scholar
Ravindran Durai Nayagam, B., Jebas, S. R., Grace, S. & Schollmeyer, D. (2008). Acta Cryst. E64, o409. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Symons, M. C. R. & West, D.-X. (1985). J. Chem. Soc. Dalton Trans. pp. 379–381. CrossRef Web of Science Google Scholar

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Volume 66| Part 2| February 2010| Pages m142-m143

https://doi.org/10.1107/S1600536810000073

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[[aqua­sodium(I)]-μ-[2,2′-(disulfanedi­yl)bis­­(pyridine N-oxide)]-μ-(pyridine-2-thiol­ato 1-oxide)]

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Experimental

Crystal data

Data collection

Refinement

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References

metal-organic compounds

catena-Poly[[aquasodium(I)]-μ-[2,2′-(disulfanediyl)bis(pyridine N-oxide)]-μ-(pyridine-2-thiolato 1-oxide)]