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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m142–m143.
Published online 2010 January 13. doi:  10.1107/S1600536810000073
PMCID: PMC2979839

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

Abstract

There are two monomeric units in the asymmetric unit of the polymeric title compound, [Na(C5H4NOS)(C10H8N2O2S2)(H2O)]n. The NaI 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 [triangle]); Symons et al. (1985 [triangle]). For their involvement in DNA strand scission under physiological conditions, see: Katsuyuki et al. (1991 [triangle]); Bovin et al. (1992 [triangle]). Pyridine N-oxides bearing a sulfur group in position two display significant anti­microbial activity, see: Leonard et al. (1955 [triangle]). For related structures, see: Jebas et al. (2005 [triangle]); Ravindran et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m142-scheme1.jpg

Experimental

Crystal data

  • [Na(C5H4NOS)(C10H8N2O2S2)(H2O)]
  • M r = 838.92
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m142-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.074
  • S = 0.93
  • 8403 reflections
  • 469 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.23 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4068 Friedel pairs
  • Flack parameter: 0.47 (6)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000073/bt5158Isup2.hkl

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

supplementary crystallographic information

Comment

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 NaI 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.

Experimental

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.

Refinement

After checking their presence in the Fourier map, all the aromatic hydrogen atoms were fixed on the calculated positions and allowed to ride on their parent atoms with the C—H = 0.95 Å. The water hydrogen atoms were located from the Fourier map and allowed to refine freely with the distances O—H = 0.86 to 0.92Å (water) with Uiso(C) in the range of 1.2Uequ(C) and 1.5Uequ(O) water. The crystal was an inversion twin. The Flack parameter indicates the fractional contribution of the twin components.

Figures

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.

Crystal data

[Na(C5H4NOS)(C10H8N2O2S2)(H2O)]F(000) = 1728
Mr = 838.92Dx = 1.600 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2acCell parameters from 6853 reflections
a = 24.829 (2) Åθ = 2.7–27.9°
b = 7.3290 (7) ŵ = 0.48 mm1
c = 19.1378 (17) ÅT = 173 K
V = 3482.5 (5) Å3Block, colorless
Z = 40.54 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer8403 independent reflections
Radiation source: sealed Tube6205 reflections with I > 2σ(I)
graphiteRint = 0.077
CCD scanθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)h = −32→30
Tmin = 0.782, Tmax = 0.936k = −9→9
38861 measured reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: calc
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.074w = 1/[σ2(Fo2) + (0.0277P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
8403 reflectionsΔρmax = 0.28 e Å3
469 parametersΔρmin = −0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 4068 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.47 (6)

Special details

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)

xyzUiso*/Ueq
Na10.62174 (8)0.7233 (3)0.43117 (11)0.0209 (4)
Na20.63035 (8)0.2253 (3)0.42791 (11)0.0205 (4)
N10.55812 (13)0.4551 (4)0.55069 (17)0.0169 (6)
C20.5074 (3)0.5199 (5)0.5651 (4)0.0192 (12)
C30.4871 (3)0.5177 (5)0.6318 (4)0.0254 (14)
H30.45180.56120.64130.031*
C40.51902 (17)0.4511 (5)0.6844 (2)0.0284 (8)
H40.50590.44820.73100.034*
C50.57028 (13)0.3880 (5)0.66984 (17)0.0261 (8)
H50.59230.34190.70640.031*
C60.58936 (13)0.3919 (4)0.60254 (17)0.0233 (7)
H60.62470.34980.59270.028*
O70.57443 (13)0.4583 (4)0.48528 (17)0.0221 (6)
S80.47870 (3)0.60118 (11)0.48539 (5)0.02044 (17)
S90.40763 (3)0.71334 (11)0.51954 (5)0.02278 (18)
C100.3632 (2)0.5278 (6)0.5114 (3)0.0194 (10)
N110.31067 (11)0.5830 (4)0.50875 (14)0.0217 (6)
C120.27083 (19)0.4613 (6)0.4983 (3)0.0257 (10)
H120.23480.50320.49310.031*
C130.28145 (15)0.2766 (6)0.49496 (19)0.0247 (9)
H130.25300.19220.48730.030*
C140.33365 (14)0.2158 (5)0.50285 (17)0.0245 (8)
H140.34140.08890.50260.029*
C150.37491 (14)0.3433 (5)0.51114 (17)0.0208 (7)
H150.41110.30340.51660.025*
O160.30158 (11)0.7595 (4)0.51612 (17)0.0334 (7)
N170.68938 (18)0.4697 (4)0.3143 (2)0.0169 (8)
C180.65984 (13)0.3867 (4)0.26226 (16)0.0202 (7)
C190.68407 (14)0.3771 (5)0.19601 (17)0.0263 (8)
H190.66450.32370.15850.032*
C200.73511 (18)0.4424 (6)0.1836 (2)0.0320 (9)
H200.75080.43170.13850.038*
C210.7630 (2)0.5230 (5)0.2370 (3)0.0292 (13)
H210.79810.57050.22880.035*
C220.7405 (2)0.5353 (5)0.3019 (3)0.0234 (10)
H220.76030.58950.33900.028*
O230.67089 (18)0.4834 (3)0.3798 (3)0.0219 (9)
S240.59697 (3)0.30128 (11)0.28014 (5)0.02486 (19)
N250.5601 (2)0.9741 (4)0.5395 (3)0.0210 (9)
C260.51021 (18)1.0416 (6)0.5488 (2)0.0223 (9)
H260.49231.09620.51030.027*
C270.4846 (2)1.0345 (6)0.6115 (3)0.0295 (11)
H270.44901.08070.61660.035*
C280.5116 (2)0.9575 (6)0.6683 (2)0.0347 (10)
H280.49480.95020.71280.042*
C290.56242 (15)0.8933 (5)0.65881 (19)0.0320 (8)
H290.58100.84480.69800.038*
C300.58885 (13)0.8950 (4)0.59367 (17)0.0230 (7)
O310.58128 (18)0.9846 (3)0.4763 (2)0.0212 (9)
S320.65125 (3)0.80270 (12)0.57957 (5)0.0296 (2)
C330.8877 (2)0.0209 (5)0.3402 (3)0.0169 (10)
N340.93985 (10)0.0766 (4)0.34558 (13)0.0190 (6)
C350.97985 (18)−0.0463 (6)0.3550 (2)0.0258 (9)
H351.0159−0.00580.36120.031*
C360.96829 (16)−0.2304 (6)0.3558 (2)0.0292 (10)
H360.9966−0.31610.36200.035*
C370.91595 (14)−0.2915 (5)0.34758 (18)0.0269 (8)
H370.9080−0.41830.34690.032*
C380.87541 (14)−0.1622 (5)0.34031 (18)0.0233 (7)
H380.8390−0.20040.33540.028*
O390.94960 (10)0.2526 (4)0.33994 (15)0.0264 (6)
S400.84312 (3)0.20813 (11)0.33478 (5)0.02221 (17)
S410.77227 (3)0.09806 (11)0.37045 (5)0.01945 (17)
C420.7423 (3)0.0149 (4)0.2941 (4)0.0157 (12)
N430.69222 (13)−0.0467 (4)0.30792 (17)0.0180 (7)
C440.65899 (13)−0.1106 (4)0.25716 (17)0.0219 (7)
H440.6236−0.14970.26840.026*
C450.67693 (13)−0.1180 (5)0.18980 (18)0.0271 (8)
H450.6539−0.16130.15380.033*
C460.72926 (16)−0.0620 (5)0.17386 (19)0.0265 (8)
H460.7423−0.07000.12730.032*
C470.7618 (3)0.0052 (4)0.2263 (4)0.0214 (14)
H470.79740.04450.21610.026*
O480.67633 (12)−0.0393 (3)0.37434 (17)0.0203 (6)
O490.69056 (8)0.1936 (3)0.52554 (13)0.0271 (5)
H49A0.72620.19200.51740.041*
H49B0.68800.07280.53100.041*
O500.56110 (8)0.6934 (3)0.33598 (13)0.0257 (5)
H50A0.52440.71150.33560.039*
H50B0.57000.58390.32390.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Na10.0196 (7)0.0196 (11)0.0234 (7)0.0009 (7)0.0026 (5)−0.0003 (7)
Na20.0203 (8)0.0189 (10)0.0223 (6)−0.0018 (7)0.0016 (6)0.0016 (7)
N10.0154 (16)0.0172 (12)0.0182 (17)0.0009 (15)0.0026 (12)0.0005 (15)
C20.015 (3)0.0152 (18)0.027 (3)−0.0043 (15)−0.002 (2)−0.0050 (16)
C30.022 (3)0.026 (2)0.028 (3)0.0014 (16)0.005 (3)−0.0027 (16)
C40.034 (2)0.034 (2)0.0177 (19)−0.003 (2)0.0063 (17)−0.0016 (18)
C50.0275 (18)0.0252 (17)0.0256 (19)−0.0014 (15)−0.0027 (15)0.0018 (15)
C60.0184 (16)0.0214 (16)0.0300 (19)0.0002 (14)−0.0039 (15)−0.0012 (15)
O70.0259 (15)0.0232 (11)0.0173 (14)0.0010 (14)0.0057 (12)0.0016 (14)
S80.0167 (4)0.0223 (4)0.0223 (4)−0.0001 (3)0.0008 (3)−0.0001 (4)
S90.0176 (4)0.0174 (4)0.0334 (5)0.0008 (3)−0.0010 (4)−0.0023 (4)
C100.020 (2)0.0223 (17)0.015 (2)−0.0022 (17)0.0002 (18)0.0049 (17)
N110.0185 (15)0.0199 (15)0.0268 (17)0.0000 (12)−0.0002 (12)−0.0030 (13)
C120.017 (2)0.0306 (18)0.030 (3)0.003 (2)−0.0022 (17)−0.005 (2)
C130.025 (2)0.029 (2)0.020 (2)−0.0078 (17)−0.0006 (15)−0.0038 (17)
C140.0280 (19)0.0205 (17)0.025 (2)0.0015 (15)0.0032 (15)−0.0023 (14)
C150.0201 (17)0.0221 (18)0.0203 (18)0.0025 (14)−0.0007 (15)0.0015 (14)
O160.0310 (17)0.0227 (14)0.0466 (18)0.0028 (13)0.0001 (15)−0.0032 (13)
N170.017 (2)0.0170 (13)0.0162 (19)0.0016 (14)0.0036 (15)0.0023 (15)
C180.0254 (17)0.0142 (15)0.0211 (18)0.0072 (14)−0.0027 (14)0.0027 (13)
C190.036 (2)0.0246 (17)0.0183 (19)0.0091 (16)0.0015 (15)0.0015 (14)
C200.040 (3)0.034 (2)0.023 (2)0.012 (2)0.0086 (18)0.007 (2)
C210.025 (3)0.028 (2)0.035 (3)0.0056 (17)0.010 (2)0.0114 (19)
C220.024 (2)0.0194 (15)0.026 (2)−0.0023 (19)0.0003 (17)0.0041 (18)
O230.023 (2)0.0225 (15)0.020 (2)−0.0003 (10)0.0026 (16)0.0006 (11)
S240.0188 (4)0.0237 (4)0.0321 (5)0.0009 (3)−0.0039 (4)−0.0021 (4)
N250.022 (2)0.0149 (13)0.026 (2)−0.0064 (14)−0.0042 (16)−0.0020 (15)
C260.014 (2)0.0229 (16)0.030 (2)−0.0051 (19)0.0006 (16)−0.0032 (19)
C270.023 (2)0.0294 (19)0.036 (3)0.001 (2)0.004 (2)−0.005 (2)
C280.039 (3)0.039 (2)0.025 (2)−0.012 (2)0.0154 (19)−0.003 (2)
C290.044 (2)0.0296 (18)0.0219 (19)−0.0083 (17)−0.0064 (17)0.0028 (16)
C300.0276 (18)0.0170 (15)0.0245 (19)−0.0078 (14)−0.0031 (15)0.0011 (14)
O310.027 (2)0.0212 (15)0.0157 (19)−0.0011 (10)0.0056 (16)0.0035 (10)
S320.0226 (5)0.0258 (4)0.0404 (5)−0.0033 (4)−0.0080 (4)0.0061 (4)
C330.013 (2)0.0204 (19)0.018 (2)−0.0027 (14)0.0012 (18)0.0048 (16)
N340.0184 (15)0.0208 (15)0.0177 (15)−0.0004 (11)0.0012 (12)0.0011 (12)
C350.016 (2)0.0321 (19)0.029 (3)0.006 (2)0.0015 (17)0.005 (2)
C360.028 (2)0.025 (2)0.034 (2)0.0109 (17)0.0112 (17)0.0102 (17)
C370.0299 (19)0.0197 (17)0.031 (2)0.0030 (16)0.0082 (16)0.0029 (15)
C380.0214 (18)0.0237 (18)0.0247 (19)−0.0026 (14)0.0021 (16)0.0014 (15)
O390.0208 (14)0.0211 (14)0.0372 (16)−0.0042 (11)−0.0021 (13)0.0015 (11)
S400.0160 (4)0.0168 (4)0.0338 (5)−0.0014 (3)−0.0001 (4)0.0036 (4)
S410.0157 (4)0.0201 (4)0.0226 (4)−0.0007 (3)0.0008 (3)0.0012 (4)
C420.017 (3)0.0138 (18)0.017 (3)0.0040 (13)0.002 (2)−0.0006 (13)
N430.0181 (16)0.0150 (12)0.0211 (17)0.0051 (15)0.0019 (13)−0.0011 (15)
C440.0158 (16)0.0209 (16)0.0291 (19)−0.0009 (14)0.0009 (14)−0.0031 (14)
C450.0243 (18)0.0305 (19)0.026 (2)0.0017 (15)−0.0063 (15)−0.0036 (16)
C460.034 (2)0.0272 (18)0.0185 (19)0.004 (2)0.0053 (16)−0.0049 (17)
C470.019 (3)0.024 (3)0.021 (3)0.0018 (12)0.005 (2)0.0008 (13)
O480.0208 (14)0.0218 (10)0.0183 (15)−0.0017 (13)0.0060 (11)0.0025 (14)
O490.0188 (11)0.0225 (12)0.0399 (14)0.0010 (10)0.0010 (10)0.0065 (11)
O500.0181 (11)0.0247 (12)0.0343 (13)0.0037 (10)−0.0003 (10)−0.0038 (11)

Geometric parameters (Å, °)

Na1—O312.328 (4)C21—C221.366 (8)
Na1—O232.355 (4)C21—H210.9500
Na1—O502.373 (3)C22—H220.9500
Na1—O48i2.459 (3)N25—O311.321 (7)
Na1—O72.495 (3)N25—C261.345 (6)
Na1—S322.990 (3)N25—C301.387 (6)
Na1—H50B2.6283C26—C271.360 (7)
Na2—O232.332 (4)C26—H260.9500
Na2—O31ii2.335 (4)C27—C281.397 (7)
Na2—O492.404 (3)C27—H270.9500
Na2—O72.459 (3)C28—C291.358 (6)
Na2—O482.473 (3)C28—H280.9500
Na2—S242.999 (2)C29—C301.409 (5)
N1—O71.316 (4)C29—H290.9500
N1—C61.342 (4)C30—S321.712 (4)
N1—C21.374 (7)O31—Na2i2.335 (4)
C2—C31.372 (10)C33—N341.362 (6)
C2—S81.785 (7)C33—C381.377 (4)
C3—C41.371 (8)C33—S401.766 (5)
C3—H30.9500N34—O391.317 (4)
C4—C51.382 (5)N34—C351.353 (5)
C4—H40.9500C35—C361.380 (6)
C5—C61.373 (4)C35—H350.9500
C5—H50.9500C36—C371.384 (5)
C6—H60.9500C36—H360.9500
S8—S92.0536 (11)C37—C381.389 (5)
S9—C101.758 (5)C37—H370.9500
C10—N111.367 (6)C38—H380.9500
C10—C151.383 (5)S40—S412.0521 (11)
N11—O161.320 (4)S41—C421.750 (7)
N11—C121.347 (5)C42—N431.348 (7)
C12—C131.380 (6)C42—C471.386 (10)
C12—H120.9500N43—O481.332 (4)
C13—C141.379 (5)N43—C441.358 (4)
C13—H130.9500C44—C451.365 (4)
C14—C151.396 (5)C44—H440.9500
C14—H140.9500C45—C461.396 (5)
C15—H150.9500C45—H450.9500
N17—O231.339 (7)C46—C471.380 (8)
N17—C221.378 (6)C46—H460.9500
N17—C181.378 (5)C47—H470.9500
C18—C191.405 (4)O48—Na1ii2.459 (3)
C18—S241.716 (3)O49—H49A0.8987
C19—C201.375 (6)O49—H49B0.8936
C19—H190.9500O50—H50A0.9220
C20—C211.368 (7)O50—H50B0.8634
C20—H200.9500
O31—Na1—O23172.9 (2)C12—C13—H13120.3
O31—Na1—O5094.98 (15)C13—C14—C15119.1 (3)
O23—Na1—O5086.52 (14)C13—C14—H14120.5
O31—Na1—O48i79.63 (13)C15—C14—H14120.5
O23—Na1—O48i93.33 (13)C10—C15—C14120.0 (4)
O50—Na1—O48i94.33 (12)C10—C15—H15120.0
O31—Na1—O7106.45 (14)C14—C15—H15120.0
O23—Na1—O780.56 (13)O23—N17—C22116.8 (4)
O50—Na1—O787.02 (11)O23—N17—C18121.8 (4)
O48i—Na1—O7173.66 (15)C22—N17—C18121.4 (4)
O31—Na1—S3266.01 (13)N17—C18—C19116.5 (3)
O23—Na1—S32114.50 (14)N17—C18—S24120.1 (3)
O50—Na1—S32154.47 (11)C19—C18—S24123.4 (3)
O48i—Na1—S3298.48 (10)C20—C19—C18122.2 (3)
O7—Na1—S3282.68 (10)C20—C19—H19118.9
O31—Na1—Na2148.47 (11)C18—C19—H19118.9
O23—Na1—Na238.50 (10)C21—C20—C19119.2 (4)
O50—Na1—Na286.09 (7)C21—C20—H20120.4
O48i—Na1—Na2131.80 (9)C19—C20—H20120.4
O7—Na1—Na242.06 (9)C22—C21—C20120.0 (5)
S32—Na1—Na2101.31 (5)C22—C21—H21120.0
O31—Na1—Na2i37.85 (11)C20—C21—H21120.0
O23—Na1—Na2i135.08 (11)C21—C22—N17120.7 (5)
O50—Na1—Na2i96.66 (7)C21—C22—H22119.7
O48i—Na1—Na2i41.79 (8)N17—C22—H22119.7
O7—Na1—Na2i144.23 (9)N17—O23—Na2117.2 (2)
S32—Na1—Na2i78.91 (4)N17—O23—Na1128.6 (3)
Na2—Na1—Na2i173.05 (4)Na2—O23—Na1102.53 (19)
O31—Na1—H50B113.5C18—S24—Na290.25 (11)
O23—Na1—H50B68.7O31—N25—C26117.9 (4)
O50—Na1—H50B19.0O31—N25—C30120.2 (4)
O48i—Na1—H50B101.5C26—N25—C30121.9 (5)
O7—Na1—H50B77.9N25—C26—C27122.3 (5)
S32—Na1—H50B159.6N25—C26—H26118.9
Na2—Na1—H50B68.1C27—C26—H26118.9
Na2i—Na1—H50B113.8C26—C27—C28118.5 (5)
O23—Na2—O31ii173.9 (2)C26—C27—H27120.8
O23—Na2—O4996.71 (16)C28—C27—H27120.8
O31ii—Na2—O4986.74 (14)C29—C28—C27118.8 (4)
O23—Na2—O781.77 (13)C29—C28—H28120.6
O31ii—Na2—O793.04 (13)C27—C28—H28120.6
O49—Na2—O794.09 (12)C28—C29—C30123.2 (4)
O23—Na2—O48105.84 (14)C28—C29—H29118.4
O31ii—Na2—O4879.21 (13)C30—C29—H29118.4
O49—Na2—O4887.67 (11)N25—C30—C29115.2 (3)
O7—Na2—O48171.96 (15)N25—C30—S32120.9 (3)
O23—Na2—S2466.19 (13)C29—C30—S32123.9 (3)
O31ii—Na2—S24111.71 (14)N25—O31—Na1117.6 (2)
O49—Na2—S24157.31 (10)N25—O31—Na2i127.9 (2)
O7—Na2—S2497.82 (10)Na1—O31—Na2i104.43 (19)
O48—Na2—S2483.23 (10)C30—S32—Na190.28 (12)
O23—Na2—Na138.96 (11)N34—C33—C38120.2 (4)
O31ii—Na2—Na1135.80 (10)N34—C33—S40111.6 (3)
O49—Na2—Na196.87 (8)C38—C33—S40128.2 (4)
O7—Na2—Na142.81 (8)O39—N34—C35121.9 (3)
O48—Na2—Na1144.76 (9)O39—N34—C33117.5 (3)
S24—Na2—Na179.32 (4)C35—N34—C33120.6 (3)
O23—Na2—Na1ii147.27 (11)N34—C35—C36120.0 (4)
O31ii—Na2—Na1ii37.72 (10)N34—C35—H35120.0
O49—Na2—Na1ii85.78 (7)C36—C35—H35120.0
O7—Na2—Na1ii130.75 (9)C35—C36—C37120.7 (4)
O48—Na2—Na1ii41.50 (8)C35—C36—H36119.6
S24—Na2—Na1ii100.67 (5)C37—C36—H36119.6
Na1—Na2—Na1ii173.05 (4)C36—C37—C38118.1 (4)
O7—N1—C6122.1 (3)C36—C37—H37121.0
O7—N1—C2117.8 (4)C38—C37—H37121.0
C6—N1—C2120.1 (4)C33—C38—C37120.3 (4)
C3—C2—N1121.2 (5)C33—C38—H38119.8
C3—C2—S8130.7 (5)C37—C38—H38119.8
N1—C2—S8108.0 (4)C33—S40—S41102.27 (16)
C4—C3—C2118.4 (5)C42—S41—S40102.9 (2)
C4—C3—H3120.8N43—C42—C47119.3 (5)
C2—C3—H3120.8N43—C42—S41110.1 (4)
C3—C4—C5120.2 (4)C47—C42—S41130.5 (5)
C3—C4—H4119.9O48—N43—C42116.6 (4)
C5—C4—H4119.9O48—N43—C44121.1 (3)
C6—C5—C4120.0 (3)C42—N43—C44122.3 (4)
C6—C5—H5120.0N43—C44—C45119.4 (3)
C4—C5—H5120.0N43—C44—H44120.3
N1—C6—C5120.1 (3)C45—C44—H44120.3
N1—C6—H6119.9C44—C45—C46119.9 (3)
C5—C6—H6119.9C44—C45—H45120.1
N1—O7—Na2125.9 (2)C46—C45—H45120.1
N1—O7—Na1123.6 (2)C47—C46—C45119.4 (4)
Na2—O7—Na195.13 (14)C47—C46—H46120.3
C2—S8—S9101.8 (2)C45—C46—H46120.3
C10—S9—S8101.62 (18)C46—C47—C42119.6 (5)
N11—C10—C15119.3 (4)C46—C47—H47120.2
N11—C10—S9111.9 (3)C42—C47—H47120.2
C15—C10—S9128.7 (4)N43—O48—Na1ii123.8 (2)
O16—N11—C12122.6 (3)N43—O48—Na2124.4 (2)
O16—N11—C10116.7 (3)Na1ii—O48—Na296.72 (14)
C12—N11—C10120.7 (3)Na2—O49—H49A118.6
N11—C12—C13121.1 (4)Na2—O49—H49B98.2
N11—C12—H12119.5H49A—O49—H49B94.4
C13—C12—H12119.5Na1—O50—H50A128.3
C14—C13—C12119.4 (4)Na1—O50—H50B97.4
C14—C13—H13120.3H50A—O50—H50B112.6
O31—Na1—Na2—O23−177.5 (4)S24—Na2—O23—N17−43.5 (3)
O50—Na1—Na2—O2389.3 (2)Na1—Na2—O23—N17−146.4 (5)
O48i—Na1—Na2—O23−3.0 (2)Na1ii—Na2—O23—N1728.3 (5)
O7—Na1—Na2—O23179.2 (3)O49—Na2—O23—Na1−92.64 (17)
S32—Na1—Na2—O23−115.3 (2)O7—Na2—O23—Na10.54 (18)
O31—Na1—Na2—O31ii7.08 (14)O48—Na2—O23—Na1177.89 (15)
O23—Na1—Na2—O31ii−175.4 (4)S24—Na2—O23—Na1102.91 (17)
O50—Na1—Na2—O31ii−86.1 (2)Na1ii—Na2—O23—Na1174.73 (9)
O48i—Na1—Na2—O31ii−178.4 (2)O50—Na1—O23—N1752.9 (4)
O7—Na1—Na2—O31ii3.8 (2)O48i—Na1—O23—N17−41.2 (4)
S32—Na1—Na2—O31ii69.24 (19)O7—Na1—O23—N17140.5 (4)
O31—Na1—Na2—O49−85.3 (3)S32—Na1—O23—N17−142.1 (4)
O23—Na1—Na2—O4992.2 (2)Na2—Na1—O23—N17141.0 (5)
O50—Na1—Na2—O49−178.48 (13)Na2i—Na1—O23—N17−43.0 (5)
O48i—Na1—Na2—O4989.20 (15)O50—Na1—O23—Na2−88.09 (17)
O7—Na1—Na2—O49−88.60 (15)O48i—Na1—O23—Na2177.77 (17)
S32—Na1—Na2—O49−23.15 (7)O7—Na1—O23—Na2−0.54 (18)
O31—Na1—Na2—O73.3 (3)S32—Na1—O23—Na276.89 (19)
O23—Na1—Na2—O7−179.2 (3)Na2i—Na1—O23—Na2175.96 (7)
O50—Na1—Na2—O7−89.89 (15)N17—C18—S24—Na2−30.1 (3)
O48i—Na1—Na2—O7177.8 (3)C19—C18—S24—Na2149.7 (3)
S32—Na1—Na2—O765.44 (13)O23—Na2—S24—C1833.22 (15)
O31—Na1—Na2—O48179.0 (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—O4885.81 (18)O7—Na2—S24—C18110.60 (14)
O48i—Na1—Na2—O48−6.51 (11)O48—Na2—S24—C18−77.44 (13)
O7—Na1—Na2—O48175.7 (3)Na1—Na2—S24—C1871.81 (11)
S32—Na1—Na2—O48−118.86 (18)Na1ii—Na2—S24—C18−115.26 (11)
O31—Na1—Na2—S24117.3 (3)O31—N25—C26—C27178.8 (4)
O23—Na1—Na2—S24−65.2 (2)C30—N25—C26—C27−0.9 (6)
O50—Na1—Na2—S2424.16 (7)N25—C26—C27—C281.4 (7)
O48i—Na1—Na2—S24−68.16 (13)C26—C27—C28—C290.1 (7)
O7—Na1—Na2—S24114.04 (15)C27—C28—C29—C30−2.1 (6)
S32—Na1—Na2—S24179.49 (8)O31—N25—C30—C29179.3 (3)
O7—N1—C2—C3178.7 (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—S32177.6 (3)
C6—N1—C2—S8177.5 (3)C28—C29—C30—N252.4 (5)
N1—C2—C3—C40.8 (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—Na147.0 (5)
C3—C4—C5—C60.0 (6)C26—N25—O31—Na2i87.3 (5)
O7—N1—C6—C5−178.8 (3)C30—N25—O31—Na2i−92.9 (4)
C2—N1—C6—C51.5 (5)O50—Na1—O31—N25117.2 (4)
C4—C5—C6—N1−0.7 (5)O48i—Na1—O31—N25−149.3 (4)
C6—N1—O7—Na237.1 (5)O7—Na1—O31—N2528.9 (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—N2526.6 (5)
C2—N1—O7—Na189.0 (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—N144.0 (3)O48i—Na1—O31—Na2i−0.94 (18)
O49—Na2—O7—N1−43.0 (3)O7—Na1—O31—Na2i177.20 (15)
S24—Na2—O7—N1156.4 (3)S32—Na1—O31—Na2i103.27 (18)
Na1—Na2—O7—N1−138.7 (3)Na2—Na1—O31—Na2i174.91 (10)
Na1ii—Na2—O7—N145.0 (3)N25—C30—S32—Na1−28.0 (3)
O23—Na2—O7—Na1−0.50 (16)C29—C30—S32—Na1150.4 (3)
O31ii—Na2—O7—Na1−177.35 (15)O31—Na1—S32—C3032.34 (16)
O49—Na2—O7—Na195.70 (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—C30106.95 (14)
O31—Na1—O7—N1−38.2 (3)O7—Na1—S32—C30−79.35 (13)
O23—Na1—O7—N1140.5 (3)Na2—Na1—S32—C30−117.25 (11)
O50—Na1—O7—N1−132.5 (3)Na2i—Na1—S32—C3069.83 (11)
S32—Na1—O7—N124.1 (3)C38—C33—N34—O39175.1 (4)
Na2—Na1—O7—N1140.0 (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—C35175.5 (3)
O23—Na1—O7—Na20.50 (16)O39—N34—C35—C36−175.5 (4)
O50—Na1—O7—Na287.46 (13)C33—N34—C35—C363.2 (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—S94.4 (4)N34—C33—C38—C371.4 (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—C331.1 (6)
S8—S9—C10—N11−159.6 (3)N34—C33—S40—S41−155.9 (3)
S8—S9—C10—C1524.0 (5)C38—C33—S40—S4123.2 (5)
C15—C10—N11—O16173.5 (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—C475.9 (4)
S9—C10—N11—C12176.0 (3)C47—C42—N43—O48177.9 (3)
O16—N11—C12—C13−176.1 (4)S41—C42—N43—O48−2.2 (4)
C10—N11—C12—C134.7 (7)C47—C42—N43—C44−3.2 (5)
N11—C12—C13—C140.4 (6)S41—C42—N43—C44176.7 (3)
C12—C13—C14—C15−2.7 (5)O48—N43—C44—C45−179.3 (3)
N11—C10—C15—C144.9 (7)C42—N43—C44—C451.8 (5)
S9—C10—C15—C14−178.9 (4)N43—C44—C45—C460.7 (5)
C13—C14—C15—C100.0 (5)C44—C45—C46—C47−1.8 (5)
O23—N17—C18—C19−178.6 (3)C45—C46—C47—C420.4 (6)
C22—N17—C18—C19−1.6 (5)N43—C42—C47—C462.0 (5)
O23—N17—C18—S241.3 (5)S41—C42—C47—C46−177.9 (3)
C22—N17—C18—S24178.3 (3)C42—N43—O48—Na1ii−141.7 (3)
N17—C18—C19—C201.6 (5)C44—N43—O48—Na1ii39.4 (4)
S24—C18—C19—C20−178.2 (3)C42—N43—O48—Na289.4 (4)
C18—C19—C20—C21−1.4 (6)C44—N43—O48—Na2−89.6 (4)
C19—C20—C21—C221.0 (6)O23—Na2—O48—N43−38.0 (3)
C20—C21—C22—N17−1.0 (6)O31ii—Na2—O48—N43138.5 (3)
O23—N17—C22—C21178.5 (4)O49—Na2—O48—N43−134.3 (3)
C18—N17—C22—C211.4 (6)S24—Na2—O48—N4324.8 (3)
C22—N17—O23—Na2−133.1 (3)Na1—Na2—O48—N43−35.7 (4)
C18—N17—O23—Na244.0 (5)Na1ii—Na2—O48—N43139.4 (3)
C22—N17—O23—Na190.6 (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—N17120.9 (3)O49—Na2—O48—Na1ii86.26 (13)
O7—Na2—O23—N17−145.9 (4)S24—Na2—O48—Na1ii−114.56 (11)
O48—Na2—O23—N1731.4 (4)Na1—Na2—O48—Na1ii−175.12 (8)

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

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the N34/C33–C35 ring.
D—H···AD—HH···AD···AD—H···A
O49—H49A···O16iii0.901.912.784 (3)165
O49—H49A···N11iii0.902.673.417 (3)141
O49—H49B···S32ii0.892.373.198 (2)154
O50—H50A···O39iv0.921.882.798 (3)177
O50—H50A···N34iv0.922.623.455 (3)151
O50—H50B···S240.862.333.193 (2)174
C29—H29···Cg1v0.952.893.618 (4)134

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5158).

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