PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): m586–m587.
Published online 2008 March 29. doi:  10.1107/S1600536808008015
PMCID: PMC2961004

Poly[tris{μ2-4-[4-(di­methyl­amino)­phenyl­diazenyl]benzene­sulfonato}tri­dioxane­tri­sodium(I)]

Abstract

The title compound, [Na3(C14H14N3O3S)3(C4H8O2)3]n, is a polynuclear complex which includes, in the monomeric unit, three units of NaI-4′-dimethyl­amino­azobenzene-4-sulfonate [known as methyl orange (MO)] and three molecules of dioxane (C4H8O2). These constitute three kinds of NaI centres, two of which are seven-coordinate while the third is five-coordinate. One of the seven-coordinate centres is coordinated by six O atoms from the sulfonate groups of four different MOs and by one O atom from dioxane. The other is coordinated by seven O atoms from the sulfonate groups of five different MOs. The five-coordinate centre is coordinated by three O atoms from the sulfonate groups of three different MOs and two O atoms from two different dioxanes. In the crystal structure, a one-dimensional polymer chain is formed along the a axis and this ensures the thermal stability of the title compound. It is also to be noted that the N=N bond lengths of the three azo groups are appreciably different [1.259 (4), 1.196 (4), and 1.253 (4) Å].

Related literature

For general background on azo pigments, see: Herbst & Hunger (2004 [triangle]). For solvated methyl orange, see: Hanson (1973 [triangle]); Kennedy et al. (2004 [triangle]). For 4′-dimethyl­amino­azobenzene-4-sulfonic acid, see: Burke et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m586-scheme1.jpg

Experimental

Crystal data

  • [Na3(C14H14N3O3S)3(C4H8O2)3]
  • M r = 1246.34
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m586-efi5.jpg
  • a = 8.4471 (6) Å
  • b = 15.5153 (10) Å
  • c = 44.488 (3) Å
  • V = 5830.6 (7) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 2.01 mm−1
  • T = 93 (1) K
  • 0.45 × 0.08 × 0.07 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (Higashi, 1995 [triangle]) T min = 0.468, T max = 0.869
  • 47815 measured reflections
  • 10385 independent reflections
  • 6459 reflections with F 2 > 2σ(F 2)
  • R int = 0.088

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.085
  • S = 0.81
  • 10385 reflections
  • 764 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.43 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 4457 Friedel pairs
  • Flack parameter: 0.006 (14)

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2006 [triangle]); program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008015/is2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008015/is2280Isup2.hkl

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

supplementary crystallographic information

Comment

We are involved in the color generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N=N–). However, some types of azo pigments are also known to possess the hydrazone structure (=N—NH–), often leading to the formation of intramolecular hydrogen bonds (Herbst & Hunger, 2004). Methyl orange (MO) (NaO3SC6H4N=NC6H4NMe2), the skeleton of the title compound, is known as one of the classical azo pigments and its structure which includes solvent molecules as ligands have been determined by Hanson (1973) and Kennedy et al. (2004). These papers report the N/N distance to be about 1.24 Å, i.e. the typical distance of the –N=N– bond. On the other hand, the methyl orange derivative (HO3SC6H4N=NC6H4NMe2: 4'-dimethylaminoazobenzene-4-sulfonic acid) in which the Na atom is replace by H atom has been found to possess a zwitterionic structure in the solid state: -O3SC6H4NH+=NC6H4NMe as characterized by a NH···O intermolecular hydrogen bond between the NH group of one molecule and one of the sulfate oxygen atoms (Burke et al., 2004). This structure reveals a lengthening of the N=N bond to 1.307 (3) Å, indicating a hydrozone-like structure. In addition, the color of the crystal is no more orange but red violet. This motivated us to study the correlation between the crystal structure and the color in these two compounds. In the course of this study, a new MO complex has been found and its structure has been determined in the present investigation.

Figure 1 shows the ORTEPIII plot (Burnett & Johnson, 1996) of the monomeric unit of (I). The asymmetric unit includes three MO molecules together with three dioxane ones. These constitute three kinds of Na(I)-complexes, two of which are seven-coordinate and the other is five-coordinate. As shown in Fig. 2, there are two kinds of seven-coordinate complexes, one of which is chelated by six O atoms from the sulfonic group of four different MOs and also by one O atom from dioxane. The other is coordinated by seven O atoms from the sulfonic group of five different MOs. The five-coordinate complex includes three O atoms from the sulfonic group of three different MOs as well as two O atoms from the two different dioxanes. It is also important to note that the N/N bond lengths are typical of the azo group (–N=N–) but these are significantly different: 1.259 (4) Å for N1/N2, 1.196 (5) Å for N4/N5, and 1.253 (4) Å for N7/N8. The monomeric unit is extended alternately to form a one dimensional polymer along the a axis as shown in Fig. 3.

Experimental

MO was purchased from Junsei Chemical Co., Ltd. Single crystals of (I) were grown by recrystallization from a dimethylacetamide solution by slow diffusion of 1,4-dioxane. After a week, a number of orange needle-like single crystals were obtained.

Refinement

All H atoms were placed in geometrically idealized position and constrained to ride on their parent atoms, with C—H = 0.95, 0.98 and 0.99 Å, and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
A view of the monomeric structure of (I), showing 50% displacement ellipsoids.
Fig. 2.
The three kinds of Na-complexes: five-coordinate Na1, seven-coordinate Na2 and Na3 [symmetry codes: (i) 1/2 + x, 1/2 - y, 1 - z; (ii) -1/2 + x, 1/2 - y, 1 - z].
Fig. 3.
The crystal packing of the title compound.

Crystal data

[Na3(C14H14N3O3S)3(C4H8O2)3]F000 = 2616.00
Mr = 1246.34Dx = 1.420 Mg m3
Orthorhombic, P212121Cu Kα radiation λ = 1.54187 Å
Hall symbol: P 2ac 2abCell parameters from 37788 reflections
a = 8.4471 (6) Åθ = 3.0–69.5º
b = 15.5153 (10) ŵ = 2.01 mm1
c = 44.488 (3) ÅT = 93 (1) K
V = 5830.6 (7) Å3Needle, orange
Z = 40.45 × 0.08 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer6459 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.088
ω scansθmax = 68.2º
Absorption correction: multi-scan(Higashi, 1995)h = −9→9
Tmin = 0.468, Tmax = 0.869k = −18→18
47815 measured reflectionsl = −53→52
10385 independent reflections

Refinement

Refinement on F2  w = 1/[σ2(Fo2) + (0.0379P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.045(Δ/σ)max = 0.001
wR(F2) = 0.085Δρmax = 0.36 e Å3
S = 0.81Δρmin = −0.43 e Å3
10385 reflectionsExtinction correction: none
764 parametersAbsolute structure: Flack (1983), 4457 Friedel pairs
H-atom parameters constrainedFlack parameter: 0.006 (14)

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
S1−0.22723 (12)0.51838 (6)0.500329 (18)0.0235 (2)
S20.24529 (12)0.33481 (6)0.444409 (17)0.0228 (2)
S3−0.23478 (12)0.15835 (6)0.469265 (17)0.0207 (2)
Na10.14117 (17)0.50896 (9)0.48393 (3)0.0364 (4)
Na2−0.05298 (15)0.30286 (8)0.49922 (3)0.0222 (3)
Na30.06100 (16)0.11580 (8)0.52800 (3)0.0247 (3)
O1−0.1035 (2)0.57736 (15)0.49049 (5)0.0289 (6)
O2−0.1910 (2)0.42862 (14)0.49340 (5)0.0263 (6)
O3−0.3846 (2)0.54162 (14)0.48945 (5)0.0272 (6)
O40.3013 (2)0.42185 (14)0.45153 (5)0.0288 (6)
O50.0808 (2)0.32228 (16)0.45286 (5)0.0307 (6)
O60.3528 (3)0.26919 (14)0.45582 (4)0.0284 (6)
O7−0.2901 (2)0.24718 (13)0.47370 (4)0.0219 (6)
O8−0.0744 (2)0.14658 (14)0.48053 (4)0.0212 (5)
O9−0.3498 (2)0.09663 (14)0.48117 (4)0.0229 (6)
O100.2588 (3)0.61217 (16)0.51733 (5)0.0493 (8)
O110.3014 (3)0.7091 (2)0.57093 (7)0.0600 (9)
O120.1835 (3)0.60985 (16)0.44754 (6)0.0412 (7)
O130.2640 (3)0.69209 (16)0.39299 (5)0.0384 (7)
O140.1498 (2)0.07239 (16)0.57779 (5)0.0301 (6)
O150.3011 (3)0.03688 (16)0.63339 (5)0.0354 (7)
N1−0.2081 (3)0.54629 (18)0.63447 (6)0.0288 (8)
N2−0.2712 (3)0.48628 (18)0.64929 (6)0.0284 (7)
N3−0.2357 (4)0.4979 (2)0.77516 (6)0.0410 (9)
N40.2901 (4)0.2991 (2)0.30969 (7)0.0450 (10)
N50.2201 (4)0.3531 (2)0.29585 (8)0.0466 (10)
N60.2814 (4)0.3307 (2)0.16975 (6)0.0425 (9)
N7−0.2721 (4)0.12369 (19)0.33631 (6)0.0310 (8)
N8−0.1971 (3)0.18020 (19)0.32210 (6)0.0335 (9)
N9−0.2472 (4)0.1789 (2)0.19640 (6)0.0397 (9)
C1−0.2283 (4)0.5248 (2)0.54014 (7)0.0235 (9)
C2−0.1781 (4)0.5994 (2)0.55415 (8)0.0356 (11)
C3−0.1741 (4)0.6044 (2)0.58525 (7)0.0401 (11)
C4−0.2232 (4)0.5361 (2)0.60262 (7)0.0248 (9)
C5−0.2779 (4)0.4619 (2)0.58864 (7)0.0266 (9)
C6−0.2802 (4)0.4555 (2)0.55754 (7)0.0263 (9)
C7−0.2540 (5)0.4925 (2)0.68062 (7)0.0283 (9)
C8−0.1563 (4)0.5506 (2)0.69568 (8)0.0312 (10)
C9−0.1486 (4)0.5526 (2)0.72657 (8)0.0363 (11)
C10−0.2412 (5)0.4964 (2)0.74404 (7)0.0316 (10)
C11−0.3357 (4)0.4355 (2)0.72890 (8)0.0366 (11)
C12−0.3399 (4)0.4343 (2)0.69779 (8)0.0355 (10)
C13−0.1415 (4)0.5631 (2)0.79053 (7)0.0426 (11)
C14−0.3432 (4)0.4472 (2)0.79285 (8)0.0433 (11)
C150.2514 (4)0.3268 (2)0.40466 (7)0.0228 (8)
C160.3362 (4)0.2605 (2)0.39107 (8)0.0340 (10)
C170.3430 (4)0.2538 (2)0.36013 (8)0.0376 (11)
C180.2644 (5)0.3132 (2)0.34274 (8)0.0398 (11)
C190.1751 (4)0.3783 (2)0.35570 (8)0.0387 (11)
C200.1685 (4)0.3847 (2)0.38701 (8)0.0317 (10)
C210.2468 (6)0.3415 (2)0.26331 (8)0.0429 (12)
C220.3391 (4)0.2776 (2)0.24986 (8)0.0416 (12)
C230.3525 (5)0.2738 (2)0.21889 (8)0.0404 (11)
C240.2711 (5)0.3328 (2)0.20068 (8)0.0356 (10)
C250.1777 (4)0.3962 (2)0.21499 (8)0.0402 (12)
C260.1683 (5)0.3989 (2)0.24557 (9)0.0473 (12)
C270.3730 (5)0.2643 (2)0.15458 (8)0.0536 (13)
C280.2072 (6)0.3977 (2)0.15193 (8)0.0797 (18)
C29−0.2317 (4)0.14013 (19)0.42995 (7)0.0183 (8)
C30−0.3588 (4)0.0990 (2)0.41650 (7)0.0233 (9)
C31−0.3643 (4)0.0927 (2)0.38564 (7)0.0282 (9)
C32−0.2470 (4)0.1300 (2)0.36811 (7)0.0237 (9)
C33−0.1157 (4)0.1677 (2)0.38175 (7)0.0276 (9)
C34−0.1070 (4)0.1729 (2)0.41273 (7)0.0227 (9)
C35−0.2204 (4)0.1761 (2)0.29030 (7)0.0283 (10)
C36−0.3160 (4)0.1176 (2)0.27532 (8)0.0379 (11)
C37−0.3253 (4)0.1181 (2)0.24433 (8)0.0389 (11)
C38−0.2368 (5)0.1778 (2)0.22709 (8)0.0332 (10)
C39−0.1413 (4)0.2362 (2)0.24270 (8)0.0339 (11)
C40−0.1333 (4)0.2352 (2)0.27349 (8)0.0348 (10)
C41−0.3149 (5)0.1046 (2)0.18092 (7)0.0518 (14)
C42−0.1464 (4)0.2364 (2)0.17905 (7)0.0426 (11)
C430.2370 (6)0.7041 (2)0.51826 (10)0.0663 (15)
C440.1934 (5)0.7348 (2)0.54849 (13)0.0758 (17)
C450.3257 (5)0.6181 (2)0.57015 (9)0.0543 (14)
C460.3743 (4)0.5895 (2)0.53932 (8)0.0389 (11)
C470.3421 (5)0.6270 (3)0.44005 (10)0.0586 (14)
C480.3665 (4)0.6332 (3)0.40808 (9)0.0591 (14)
C490.1042 (5)0.6743 (3)0.40154 (9)0.0645 (15)
C500.0770 (5)0.6692 (2)0.43346 (9)0.0561 (13)
C510.2248 (4)0.1395 (2)0.59486 (7)0.0299 (9)
C520.2227 (4)0.1169 (2)0.62798 (7)0.0374 (10)
C530.2281 (4)−0.0283 (2)0.61608 (7)0.0345 (10)
C540.2307 (4)−0.0064 (2)0.58293 (7)0.0316 (10)
H2−0.14600.64750.54240.043*
H3−0.13710.65550.59470.048*
H5−0.31420.41490.60050.032*
H6−0.31680.40430.54810.032*
H8−0.09360.58980.68440.037*
H9−0.07980.59240.73620.044*
H11−0.39670.39520.74000.044*
H12−0.40350.39250.68790.043*
H13a−0.18100.62050.78530.051*
H13b−0.03060.55780.78430.051*
H13c−0.14960.55460.81230.051*
H14a−0.31740.38600.79060.052*
H14b−0.45190.45740.78600.052*
H14c−0.33380.46360.81410.052*
H160.39000.21950.40320.041*
H170.40150.20860.35100.045*
H190.11910.41810.34340.046*
H200.10710.42870.39620.038*
H220.39280.23660.26200.050*
H230.41730.23090.20990.048*
H250.12130.43700.20330.048*
H260.10490.44210.25480.057*
H27a0.48570.27260.15880.064*
H27b0.35510.26800.13290.064*
H27c0.33970.20740.16180.064*
H28a0.24260.39300.13100.096*
H28b0.23700.45430.15990.096*
H28c0.09200.39120.15280.096*
H30−0.44130.07530.42840.028*
H31−0.44900.06260.37630.034*
H33−0.03200.18990.36980.033*
H34−0.01770.19840.42220.027*
H36−0.37570.07680.28650.045*
H37−0.39200.07770.23440.047*
H39−0.08100.27730.23180.041*
H40−0.06720.27540.28350.042*
H41a−0.25760.05240.18680.062*
H41b−0.30590.11280.15920.062*
H41c−0.42680.09880.18640.062*
H42a−0.18090.23650.15800.051*
H42b−0.03650.21660.18020.051*
H42c−0.15400.29490.18720.051*
H43a0.15280.72050.50390.080*
H43b0.33610.73280.51190.080*
H44a0.18730.79850.54820.091*
H44b0.08710.71240.55360.091*
H45a0.22670.58830.57600.065*
H45b0.40890.60210.58480.065*
H46a0.47670.61660.53410.047*
H46b0.38930.52620.53930.047*
H47a0.41000.58060.44820.070*
H47b0.37490.68180.44960.070*
H48a0.47740.65080.40440.071*
H48b0.35190.57530.39920.071*
H49a0.07180.61900.39230.077*
H49b0.03520.71990.39310.077*
H50a0.09090.72700.44250.067*
H50b−0.03340.65060.43720.067*
H51a0.16840.19470.59160.036*
H51b0.33560.14680.58800.036*
H52a0.27570.16310.63950.045*
H52b0.11170.11290.63500.045*
H53a0.1171−0.03560.62280.041*
H53b0.2840−0.08360.61940.041*
H54a0.3417−0.00130.57600.038*
H54b0.1793−0.05320.57140.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0279 (6)0.0264 (5)0.0162 (4)0.0019 (5)−0.0006 (4)0.0012 (3)
S20.0255 (6)0.0286 (5)0.0142 (4)−0.0006 (5)0.0006 (4)0.0010 (3)
S30.0248 (6)0.0238 (5)0.0136 (4)0.0007 (5)0.0003 (4)−0.0008 (3)
Na10.0469 (10)0.0338 (8)0.0285 (7)0.0075 (8)0.0062 (7)0.0099 (6)
Na20.0234 (8)0.0246 (7)0.0187 (6)−0.0009 (6)0.0017 (6)0.0002 (6)
Na30.0260 (9)0.0277 (8)0.0206 (7)0.0023 (7)0.0003 (6)0.0011 (6)
O10.0337 (16)0.0338 (15)0.0193 (13)−0.0084 (13)0.0039 (12)0.0015 (11)
O20.0323 (16)0.0229 (13)0.0239 (13)0.0056 (12)−0.0026 (11)−0.0033 (10)
O30.0312 (16)0.0347 (15)0.0157 (12)0.0060 (13)−0.0040 (11)−0.0007 (11)
O40.0364 (18)0.0254 (14)0.0244 (13)−0.0094 (13)0.0024 (12)−0.0009 (10)
O50.0219 (15)0.0525 (17)0.0177 (13)−0.0041 (14)0.0037 (11)−0.0025 (12)
O60.0396 (18)0.0292 (14)0.0165 (13)0.0084 (14)−0.0028 (12)0.0020 (10)
O70.0292 (16)0.0179 (12)0.0186 (12)0.0030 (12)−0.0033 (11)−0.0025 (9)
O80.0185 (14)0.0325 (15)0.0126 (12)0.0041 (12)−0.0056 (10)0.0034 (10)
O90.0253 (15)0.0228 (14)0.0205 (13)−0.0031 (12)0.0044 (11)0.0021 (10)
O100.065 (2)0.0376 (17)0.0452 (17)0.0097 (18)−0.0302 (17)−0.0086 (13)
O110.057 (2)0.058 (2)0.065 (2)−0.0100 (19)0.0032 (19)−0.0125 (17)
O120.0334 (19)0.0430 (18)0.0471 (17)0.0066 (15)0.0023 (14)0.0237 (14)
O130.0374 (19)0.0487 (17)0.0292 (13)0.0134 (17)0.0061 (15)0.0104 (12)
O140.0334 (17)0.0327 (15)0.0244 (14)0.0021 (14)−0.0016 (12)0.0030 (12)
O150.046 (2)0.0380 (16)0.0221 (13)−0.0015 (14)−0.0059 (13)0.0031 (12)
N10.034 (2)0.0276 (19)0.0251 (17)0.0020 (16)−0.0024 (15)−0.0023 (14)
N20.027 (2)0.0351 (19)0.0231 (16)0.0001 (18)0.0032 (15)0.0032 (14)
N30.044 (2)0.057 (2)0.0221 (17)−0.008 (2)0.0027 (19)−0.0071 (16)
N40.040 (2)0.043 (2)0.053 (2)−0.009 (2)−0.014 (2)0.0018 (17)
N50.042 (2)0.039 (2)0.059 (2)−0.009 (2)−0.016 (2)0.0077 (18)
N60.071 (2)0.042 (2)0.0152 (16)0.001 (2)0.0008 (18)0.0008 (15)
N70.035 (2)0.035 (2)0.0238 (17)0.0062 (18)0.0048 (17)0.0006 (14)
N80.039 (2)0.035 (2)0.0261 (18)0.0051 (18)0.0060 (16)−0.0020 (15)
N90.057 (2)0.048 (2)0.0141 (15)−0.015 (2)−0.0007 (19)−0.0021 (14)
C10.026 (2)0.021 (2)0.0233 (19)0.003 (2)−0.0032 (18)−0.0017 (15)
C20.059 (3)0.024 (2)0.024 (2)−0.015 (2)−0.003 (2)0.0063 (17)
C30.066 (3)0.032 (2)0.022 (2)−0.011 (2)−0.003 (2)−0.0080 (17)
C40.027 (2)0.030 (2)0.0169 (19)0.002 (2)−0.0005 (18)−0.0023 (15)
C50.029 (2)0.031 (2)0.0201 (18)−0.004 (2)0.0019 (18)0.0031 (15)
C60.029 (2)0.028 (2)0.0224 (19)−0.0053 (19)0.0001 (18)−0.0075 (16)
C70.033 (2)0.034 (2)0.0183 (18)−0.007 (2)0.002 (2)−0.0071 (16)
C80.037 (2)0.031 (2)0.025 (2)−0.004 (2)−0.0013 (19)0.0040 (17)
C90.045 (3)0.036 (2)0.028 (2)−0.009 (2)−0.002 (2)−0.0088 (18)
C100.033 (2)0.040 (2)0.022 (2)0.006 (2)−0.004 (2)−0.0013 (17)
C110.038 (2)0.048 (2)0.023 (2)−0.006 (2)0.004 (2)0.0031 (19)
C120.039 (2)0.046 (2)0.021 (2)−0.005 (2)−0.0018 (19)−0.0050 (19)
C130.053 (3)0.052 (2)0.022 (2)−0.003 (2)−0.002 (2)−0.004 (2)
C140.053 (3)0.054 (2)0.023 (2)0.004 (2)−0.004 (2)0.004 (2)
C150.025 (2)0.027 (2)0.0160 (17)−0.007 (2)0.0012 (18)−0.0028 (15)
C160.038 (2)0.042 (2)0.022 (2)−0.013 (2)−0.0032 (19)−0.0002 (19)
C170.041 (2)0.046 (2)0.026 (2)0.000 (2)0.006 (2)−0.005 (2)
C180.039 (3)0.058 (3)0.022 (2)−0.025 (2)0.008 (2)−0.009 (2)
C190.035 (2)0.052 (2)0.029 (2)−0.011 (2)−0.014 (2)0.017 (2)
C200.026 (2)0.041 (2)0.028 (2)−0.001 (2)−0.0018 (18)0.0055 (19)
C210.054 (3)0.052 (3)0.023 (2)−0.023 (3)0.010 (2)−0.007 (2)
C220.052 (3)0.049 (2)0.023 (2)−0.020 (2)−0.011 (2)0.014 (2)
C230.051 (3)0.043 (2)0.027 (2)−0.008 (2)0.003 (2)−0.0016 (19)
C240.049 (3)0.036 (2)0.0219 (19)−0.012 (2)−0.003 (2)0.0025 (18)
C250.061 (3)0.035 (2)0.025 (2)−0.005 (2)0.001 (2)0.0016 (18)
C260.066 (3)0.044 (2)0.032 (2)−0.009 (2)0.003 (2)−0.009 (2)
C270.071 (3)0.058 (3)0.031 (2)−0.014 (2)0.006 (2)−0.013 (2)
C280.163 (5)0.053 (3)0.022 (2)0.017 (3)0.004 (3)0.004 (2)
C290.024 (2)0.0144 (18)0.0169 (17)0.0065 (19)−0.0037 (18)0.0019 (13)
C300.026 (2)0.026 (2)0.0177 (19)0.0006 (19)0.0035 (17)−0.0031 (16)
C310.025 (2)0.031 (2)0.028 (2)−0.004 (2)−0.0062 (18)−0.0024 (18)
C320.029 (2)0.026 (2)0.0162 (18)0.005 (2)−0.0052 (19)−0.0006 (15)
C330.025 (2)0.036 (2)0.022 (2)0.003 (2)0.0105 (17)0.0057 (17)
C340.028 (2)0.025 (2)0.0153 (18)0.0039 (19)−0.0012 (16)−0.0027 (16)
C350.033 (2)0.040 (2)0.0120 (18)0.005 (2)0.0011 (18)−0.0019 (17)
C360.052 (3)0.038 (2)0.024 (2)0.003 (2)0.003 (2)0.0045 (19)
C370.056 (3)0.039 (2)0.022 (2)−0.001 (2)−0.003 (2)−0.0018 (19)
C380.041 (2)0.040 (2)0.0192 (19)0.007 (2)−0.001 (2)−0.0003 (17)
C390.041 (3)0.045 (2)0.016 (2)0.003 (2)0.0072 (19)0.0069 (18)
C400.035 (2)0.043 (2)0.027 (2)0.000 (2)−0.005 (2)−0.0036 (19)
C410.084 (4)0.057 (3)0.014 (2)−0.002 (2)−0.002 (2)0.000 (2)
C420.052 (3)0.057 (2)0.019 (2)0.002 (2)0.000 (2)0.001 (2)
C430.078 (4)0.028 (2)0.092 (3)0.000 (3)−0.037 (3)−0.009 (2)
C440.039 (3)0.049 (3)0.140 (5)0.001 (2)−0.012 (3)−0.056 (3)
C450.066 (3)0.047 (3)0.050 (2)−0.018 (2)0.019 (2)−0.014 (2)
C460.041 (3)0.033 (2)0.043 (2)0.002 (2)−0.008 (2)−0.004 (2)
C470.032 (3)0.079 (3)0.065 (3)0.001 (2)0.001 (2)0.039 (2)
C480.038 (3)0.096 (4)0.043 (2)0.022 (3)0.011 (2)0.003 (2)
C490.044 (3)0.117 (4)0.033 (2)0.046 (3)0.005 (2)0.010 (2)
C500.052 (3)0.061 (3)0.055 (3)0.009 (2)−0.002 (2)0.025 (2)
C510.036 (2)0.027 (2)0.0266 (19)−0.004 (2)0.0048 (19)0.0032 (15)
C520.051 (3)0.038 (2)0.0231 (19)−0.005 (2)−0.004 (2)0.0004 (17)
C530.048 (3)0.027 (2)0.029 (2)0.004 (2)0.003 (2)0.0061 (17)
C540.042 (2)0.031 (2)0.0223 (19)−0.005 (2)−0.001 (2)−0.0013 (16)

Geometric parameters (Å, °)

S1—O11.457 (2)C14—H14b0.980
S1—O21.459 (2)C14—H14c0.980
S1—O31.460 (2)C15—C161.391 (5)
S1—C11.774 (3)C15—C201.383 (5)
S2—O41.465 (2)C16—C171.382 (5)
S2—O51.452 (2)C16—H160.950
S2—O61.456 (2)C17—C181.374 (5)
S2—C151.773 (3)C17—H170.950
S3—O71.469 (2)C18—C191.386 (5)
S3—O81.456 (2)C19—C201.398 (5)
S3—O91.464 (2)C19—H190.950
S3—C291.772 (3)C20—H200.950
Na1—O12.341 (2)C21—C221.396 (5)
Na1—O42.394 (2)C21—C261.362 (5)
Na1—O9i2.258 (2)C22—C231.384 (5)
Na1—O102.400 (2)C22—H220.950
Na1—O122.280 (2)C23—C241.403 (5)
Na2—O22.288 (2)C23—H230.950
Na2—O52.371 (2)C24—C251.411 (5)
Na2—O6ii2.426 (2)C25—C261.363 (5)
Na2—O72.459 (2)C25—H250.950
Na2—O7i2.643 (2)C26—H260.950
Na2—O82.570 (2)C27—H27a0.980
Na2—O9i2.477 (2)C27—H27b0.980
Na3—O2i2.402 (2)C27—H27c0.980
Na3—O3i2.604 (2)C28—H28a0.980
Na3—O4ii2.446 (2)C28—H28b0.980
Na3—O6ii2.607 (2)C28—H28c0.980
Na3—O7i2.471 (2)C29—C301.385 (5)
Na3—O82.449 (2)C29—C341.398 (4)
Na3—O142.434 (2)C30—C311.377 (4)
O10—C431.439 (4)C30—H300.950
O10—C461.425 (4)C31—C321.387 (5)
O11—C441.410 (6)C31—H310.950
O11—C451.427 (5)C32—C331.393 (5)
O12—C471.406 (5)C33—C341.383 (4)
O12—C501.432 (5)C33—H330.950
O13—C481.426 (5)C34—H340.950
O13—C491.430 (5)C35—C361.385 (5)
O14—C511.437 (4)C35—C401.393 (5)
O14—C541.420 (4)C36—C371.381 (5)
O15—C521.428 (4)C36—H360.950
O15—C531.413 (4)C37—C381.416 (5)
N1—N21.259 (4)C37—H370.950
N1—C41.431 (4)C38—C391.398 (5)
N2—C71.405 (4)C39—C401.372 (5)
N3—C101.385 (4)C39—H390.950
N3—C131.457 (4)C40—H400.950
N3—C141.436 (4)C41—H41a0.980
N4—N51.196 (4)C41—H41b0.980
N4—C181.502 (4)C41—H41c0.980
N5—C211.476 (5)C42—H42a0.980
N6—C241.379 (4)C42—H42b0.980
N6—C271.455 (5)C42—H42c0.980
N6—C281.450 (5)C43—C441.473 (7)
N7—N81.253 (4)C43—H43a0.990
N7—C321.434 (4)C43—H43b0.990
N8—C351.430 (4)C44—H44a0.990
N9—C381.368 (4)C44—H44b0.990
N9—C411.460 (4)C45—C461.499 (5)
N9—C421.455 (4)C45—H45a0.990
C1—C21.382 (4)C45—H45b0.990
C1—C61.395 (4)C46—H46a0.990
C2—C31.386 (4)C46—H46b0.990
C2—H20.950C47—C481.440 (5)
C3—C41.376 (4)C47—H47a0.990
C3—H30.950C47—H47b0.990
C4—C51.388 (4)C48—H48a0.990
C5—C61.387 (4)C48—H48b0.990
C5—H50.950C49—C501.441 (5)
C6—H60.950C49—H49a0.990
C7—C81.395 (5)C49—H49b0.990
C7—C121.387 (5)C50—H50a0.990
C8—C91.376 (5)C50—H50b0.990
C8—H80.950C51—C521.515 (4)
C9—C101.406 (5)C51—H51a0.990
C9—H90.950C51—H51b0.990
C10—C111.408 (5)C52—H52a0.990
C11—C121.385 (5)C52—H52b0.990
C11—H110.950C53—C541.514 (4)
C12—H120.950C53—H53a0.990
C13—H13a0.980C53—H53b0.990
C13—H13b0.980C54—H54a0.990
C13—H13c0.980C54—H54b0.990
C14—H14a0.980
O3···H46aiii2.581H28a···H45bxiv2.424
O3···H47aiii2.596H28b···N7v2.650
O11···H49biv2.769H40···H13aviii2.671
O11···H50aiv2.705H41a···H19vii2.742
O11···H50biv2.612H41b···O13vii2.649
O13···H3iv2.567H41b···H48bvii2.687
O13···H41bv2.649H41c···H23iii2.651
O13···H42av2.473H42a···O13vii2.473
O15···H13cvi2.748H42a···H49bvii2.600
O15···H14cvi2.615H42c···H8viii2.786
N7···H28bvii2.650H44a···H47bx2.658
C40···H13aviii2.784H44a···H50biv2.572
C45···H28aix2.774H44a···H54bxv2.522
H2···H47bx2.678H44b···H47bx2.434
H3···O13x2.567H45a···H28aix2.479
H8···H27aix2.584H45b···H28aix2.424
H8···H42cxi2.786H46a···O3xiii2.581
H13a···C40xi2.784H47a···O3xiii2.596
H13a···H40xi2.671H47b···H2iv2.678
H13c···O15xii2.748H47b···H44aiv2.658
H13c···H52bxii2.533H47b···H44biv2.434
H14b···H26xi2.456H48b···H41bv2.687
H14c···O15xii2.615H49b···O11x2.769
H19···H41av2.742H49b···H42av2.600
H23···H41cxiii2.651H50a···O11x2.705
H26···H14bviii2.456H50b···O11x2.612
H27a···H8xiv2.584H50b···H44ax2.572
H28a···C45xiv2.774H52b···H13cvi2.533
H28a···H45axiv2.479H54b···H44axvi2.522
O1—S1—O2112.68 (14)S2—C15—C16120.0 (2)
O1—S1—O3113.50 (13)S2—C15—C20120.4 (2)
O1—S1—C1105.59 (15)C16—C15—C20119.6 (3)
O2—S1—O3110.90 (13)C15—C16—C17120.7 (3)
O2—S1—C1105.39 (14)C15—C16—H16119.7
O3—S1—C1108.21 (15)C17—C16—H16119.7
O4—S2—O5112.08 (14)C16—C17—C18119.4 (3)
O4—S2—O6111.58 (13)C16—C17—H17120.3
O4—S2—C15105.72 (15)C18—C17—H17120.3
O5—S2—O6114.39 (14)N4—C18—C17112.6 (3)
O5—S2—C15106.05 (16)N4—C18—C19126.3 (3)
O6—S2—C15106.29 (14)C17—C18—C19121.1 (3)
O7—S3—O8111.56 (13)C18—C19—C20119.2 (3)
O7—S3—O9110.74 (13)C18—C19—H19120.4
O7—S3—C29106.68 (13)C20—C19—H19120.4
O8—S3—O9114.29 (12)C15—C20—C19120.0 (3)
O8—S3—C29107.83 (15)C15—C20—H20120.0
O9—S3—C29105.22 (14)C19—C20—H20120.0
O1—Na1—O4146.03 (9)N5—C21—C22126.3 (3)
O1—Na1—O9i105.83 (9)N5—C21—C26114.5 (3)
O1—Na1—O1089.19 (10)C22—C21—C26119.2 (3)
O1—Na1—O1285.18 (9)C21—C22—C23120.2 (3)
O4—Na1—O9i89.17 (8)C21—C22—H22119.9
O4—Na1—O10121.03 (10)C23—C22—H22119.9
O4—Na1—O1282.61 (9)C22—C23—C24120.5 (3)
O9i—Na1—O1092.55 (9)C22—C23—H23119.8
O9i—Na1—O12168.76 (11)C24—C23—H23119.8
O10—Na1—O1285.21 (9)N6—C24—C23122.0 (3)
O2—Na2—O592.07 (9)N6—C24—C25120.1 (3)
O2—Na2—O6ii108.62 (9)C23—C24—C25117.9 (3)
O2—Na2—O780.35 (8)C24—C25—C26120.3 (3)
O2—Na2—O7i136.91 (8)C24—C25—H25119.9
O2—Na2—O8137.09 (9)C26—C25—H25119.8
O2—Na2—O9i81.71 (8)C21—C26—C25122.0 (3)
O5—Na2—O6ii158.78 (9)C21—C26—H26119.0
O5—Na2—O791.80 (8)C25—C26—H26119.0
O5—Na2—O7i91.91 (8)N6—C27—H27a109.5
O5—Na2—O882.64 (8)N6—C27—H27b109.5
O5—Na2—O9i84.04 (8)N6—C27—H27c109.5
O6ii—Na2—O787.23 (8)H27a—C27—H27b109.5
O6ii—Na2—O7i76.37 (8)H27a—C27—H27c109.5
O6ii—Na2—O878.98 (7)H27b—C27—H27c109.5
O6ii—Na2—O9i103.11 (8)N6—C28—H28a109.5
O7—Na2—O7i142.34 (8)N6—C28—H28b109.5
O7—Na2—O857.44 (7)N6—C28—H28c109.5
O7—Na2—O9i161.42 (8)H28a—C28—H28b109.5
O7i—Na2—O885.95 (7)H28a—C28—H28c109.5
O7i—Na2—O9i56.11 (7)H28b—C28—H28c109.5
O8—Na2—O9i139.17 (8)S3—C29—C30119.3 (2)
O2i—Na3—O3i57.24 (7)S3—C29—C34119.6 (2)
O2i—Na3—O4ii149.46 (9)C30—C29—C34121.0 (2)
O2i—Na3—O6ii153.40 (9)C29—C30—C31119.3 (3)
O2i—Na3—O7i77.92 (8)C29—C30—H30120.3
O2i—Na3—O896.97 (8)C31—C30—H30120.4
O2i—Na3—O1490.72 (8)C30—C31—C32120.5 (3)
O3i—Na3—O4ii92.59 (8)C30—C31—H31119.8
O3i—Na3—O6ii147.51 (9)C32—C31—H31119.8
O3i—Na3—O7i135.08 (8)N7—C32—C31114.9 (3)
O3i—Na3—O890.47 (8)N7—C32—C33125.2 (3)
O3i—Na3—O1487.56 (8)C31—C32—C33119.9 (2)
O4ii—Na3—O6ii57.02 (7)C32—C33—C34120.1 (3)
O4ii—Na3—O7i132.32 (8)C32—C33—H33120.0
O4ii—Na3—O887.07 (8)C34—C33—H33120.0
O4ii—Na3—O1482.62 (8)C29—C34—C33119.0 (3)
O6ii—Na3—O7i76.29 (8)C29—C34—H34120.5
O6ii—Na3—O877.86 (7)C33—C34—H34120.5
O6ii—Na3—O1498.40 (8)N8—C35—C36125.9 (3)
O7i—Na3—O892.49 (7)N8—C35—C40115.4 (3)
O7i—Na3—O1496.26 (8)C36—C35—C40118.7 (3)
O8—Na3—O14169.39 (9)C35—C36—C37120.7 (3)
S1—O1—Na1112.71 (13)C35—C36—H36119.7
S1—O2—Na2153.80 (14)C37—C36—H36119.6
S1—O2—Na3ii100.05 (11)C36—C37—C38120.9 (3)
Na2—O2—Na3ii104.16 (9)C36—C37—H37119.6
S1—O3—Na3ii91.59 (10)C38—C37—H37119.5
S2—O4—Na1117.91 (12)N9—C38—C37121.0 (3)
S2—O4—Na3i98.61 (11)N9—C38—C39121.6 (3)
Na1—O4—Na3i114.66 (9)C37—C38—C39117.4 (3)
S2—O5—Na2134.29 (14)C38—C39—C40121.1 (3)
S2—O6—Na2i144.54 (12)C38—C39—H39119.5
S2—O6—Na3i92.21 (11)C40—C39—H39119.4
Na2i—O6—Na3i82.33 (7)C35—C40—C39121.2 (3)
S3—O7—Na297.62 (11)C35—C40—H40119.4
S3—O7—Na2ii93.03 (10)C39—C40—H40119.4
S3—O7—Na3ii164.82 (13)N9—C41—H41a109.5
Na2—O7—Na2ii125.25 (8)N9—C41—H41b109.5
Na2—O7—Na3ii97.27 (8)N9—C41—H41c109.5
Na2ii—O7—Na3ii80.73 (7)H41a—C41—H41b109.5
S3—O8—Na293.35 (11)H41a—C41—H41c109.5
S3—O8—Na3139.09 (12)H41b—C41—H41c109.5
Na2—O8—Na382.65 (7)N9—C42—H42a109.5
S3—O9—Na1ii138.22 (14)N9—C42—H42b109.5
S3—O9—Na2ii100.11 (11)N9—C42—H42c109.5
Na1ii—O9—Na2ii101.03 (8)H42a—C42—H42b109.5
Na1—O10—C43128.8 (2)H42a—C42—H42c109.5
Na1—O10—C46122.9 (2)H42b—C42—H42c109.5
C43—O10—C46108.2 (2)O10—C43—C44112.2 (3)
C44—O11—C45110.8 (3)O10—C43—H43a109.2
Na1—O12—C47116.6 (2)O10—C43—H43b109.2
Na1—O12—C50130.8 (2)C44—C43—H43a109.2
C47—O12—C50111.9 (3)C44—C43—H43b109.2
C48—O13—C49108.9 (2)H43a—C43—H43b107.9
Na3—O14—C51114.61 (18)O11—C44—C43113.2 (3)
Na3—O14—C54122.24 (18)O11—C44—H44a108.9
C51—O14—C54109.1 (2)O11—C44—H44b108.9
C52—O15—C53109.2 (2)C43—C44—H44a108.9
N2—N1—C4113.5 (2)C43—C44—H44b108.9
N1—N2—C7115.2 (2)H44a—C44—H44b107.7
C10—N3—C13119.9 (3)O11—C45—C46110.7 (3)
C10—N3—C14121.2 (3)O11—C45—H45a109.5
C13—N3—C14117.9 (2)O11—C45—H45b109.5
N5—N4—C18109.3 (3)C46—C45—H45a109.5
N4—N5—C21110.1 (3)C46—C45—H45b109.5
C24—N6—C27120.9 (3)H45a—C45—H45b108.1
C24—N6—C28120.1 (3)O10—C46—C45111.6 (3)
C27—N6—C28119.0 (2)O10—C46—H46a109.3
N8—N7—C32112.0 (2)O10—C46—H46b109.3
N7—N8—C35113.5 (2)C45—C46—H46a109.3
C38—N9—C41119.0 (3)C45—C46—H46b109.3
C38—N9—C42120.0 (3)H46a—C46—H46b108.0
C41—N9—C42117.6 (2)O12—C47—C48112.5 (3)
S1—C1—C2119.7 (2)O12—C47—H47a109.1
S1—C1—C6120.9 (2)O12—C47—H47b109.1
C2—C1—C6119.4 (2)C48—C47—H47a109.1
C1—C2—C3120.3 (3)C48—C47—H47b109.1
C1—C2—H2119.8H47a—C47—H47b107.8
C3—C2—H2119.9O13—C48—C47114.9 (3)
C2—C3—C4120.7 (3)O13—C48—H48a108.6
C2—C3—H3119.7O13—C48—H48b108.5
C4—C3—H3119.6C47—C48—H48a108.5
N1—C4—C3116.4 (2)C47—C48—H48b108.6
N1—C4—C5124.4 (2)H48a—C48—H48b107.5
C3—C4—C5119.2 (2)O13—C49—C50115.0 (3)
C4—C5—C6120.7 (3)O13—C49—H49a108.5
C4—C5—H5119.7O13—C49—H49b108.5
C6—C5—H5119.7C50—C49—H49a108.5
C1—C6—C5119.7 (3)C50—C49—H49b108.5
C1—C6—H6120.2H49a—C49—H49b107.5
C5—C6—H6120.2O12—C50—C49111.5 (3)
N2—C7—C8125.6 (3)O12—C50—H50a109.3
N2—C7—C12116.6 (3)O12—C50—H50b109.3
C8—C7—C12117.8 (3)C49—C50—H50a109.3
C7—C8—C9121.5 (3)C49—C50—H50b109.3
C7—C8—H8119.3H50a—C50—H50b108.0
C9—C8—H8119.3O14—C51—C52109.9 (2)
C8—C9—C10120.8 (3)O14—C51—H51a109.7
C8—C9—H9119.6O14—C51—H51b109.7
C10—C9—H9119.6C52—C51—H51a109.7
N3—C10—C9121.6 (3)C52—C51—H51b109.7
N3—C10—C11120.5 (3)H51a—C51—H51b108.2
C9—C10—C11117.8 (3)O15—C52—C51111.1 (2)
C10—C11—C12120.1 (3)O15—C52—H52a109.4
C10—C11—H11119.9O15—C52—H52b109.4
C12—C11—H11119.9C51—C52—H52a109.4
C7—C12—C11121.9 (3)C51—C52—H52b109.4
C7—C12—H12119.1H52a—C52—H52b108.0
C11—C12—H12119.1O15—C53—C54111.3 (2)
N3—C13—H13a109.5O15—C53—H53a109.4
N3—C13—H13b109.5O15—C53—H53b109.4
N3—C13—H13c109.5C54—C53—H53a109.4
H13a—C13—H13b109.5C54—C53—H53b109.3
H13a—C13—H13c109.5H53a—C53—H53b108.0
H13b—C13—H13c109.5O14—C54—C53110.1 (2)
N3—C14—H14a109.5O14—C54—H54a109.6
N3—C14—H14b109.5O14—C54—H54b109.7
N3—C14—H14c109.5C53—C54—H54a109.6
H14a—C14—H14b109.5C53—C54—H54b109.6
H14a—C14—H14c109.5H54a—C54—H54b108.2
H14b—C14—H14c109.5
O1—S1—O2—Na269.6 (3)O3i—Na3—O2i—Na2i172.73 (12)
O1—S1—O2—Na3ii−133.01 (12)O2i—Na3—O4ii—S2ii179.17 (15)
O2—S1—O1—Na1−21.26 (17)O2i—Na3—O4ii—Na1ii−54.6 (2)
O1—S1—O3—Na3ii132.15 (11)O4ii—Na3—O2i—S1i12.8 (2)
O3—S1—O1—Na1−148.38 (12)O4ii—Na3—O2i—Na2i−177.25 (15)
O1—S1—C1—C227.1 (3)O2i—Na3—O6ii—S2ii−179.71 (17)
O1—S1—C1—C6−153.2 (2)O2i—Na3—O6ii—Na235.5 (2)
C1—S1—O1—Na193.26 (16)O6ii—Na3—O2i—S1i−159.98 (16)
O2—S1—O3—Na3ii4.12 (13)O6ii—Na3—O2i—Na2i9.9 (2)
O3—S1—O2—Na2−161.9 (2)O2i—Na3—O7i—S3i−164.7 (4)
O3—S1—O2—Na3ii−4.53 (15)O2i—Na3—O7i—Na2i3.99 (8)
O2—S1—C1—C2146.6 (2)O2i—Na3—O7i—Na2128.65 (7)
O2—S1—C1—C6−33.8 (3)O7i—Na3—O2i—S1i−174.30 (12)
C1—S1—O2—Na2−45.0 (3)O7i—Na3—O2i—Na2i−4.39 (8)
C1—S1—O2—Na3ii112.34 (14)O2i—Na3—O8—S3162.35 (19)
O3—S1—C1—C2−94.7 (3)O2i—Na3—O8—Na2−111.02 (7)
O3—S1—C1—C684.9 (3)O8—Na3—O2i—S1i−83.23 (12)
C1—S1—O3—Na3ii−111.01 (13)O8—Na3—O2i—Na2i86.68 (10)
O4—S2—O5—Na2−74.3 (2)O2i—Na3—O14—C5191.7 (2)
O5—S2—O4—Na113.40 (18)O2i—Na3—O14—C54−43.8 (2)
O5—S2—O4—Na3i137.30 (11)O14—Na3—O2i—S1i89.45 (12)
O4—S2—O6—Na2i72.9 (2)O14—Na3—O2i—Na2i−100.64 (10)
O4—S2—O6—Na3i−6.98 (13)O3i—Na3—O4ii—S2ii−172.40 (11)
O6—S2—O4—Na1−116.38 (14)O3i—Na3—O4ii—Na1ii−46.21 (11)
O6—S2—O4—Na3i7.52 (14)O4ii—Na3—O3i—S1i−177.69 (11)
O4—S2—C15—C16124.6 (3)O3i—Na3—O6ii—S2ii27.87 (19)
O4—S2—C15—C20−57.2 (3)O3i—Na3—O6ii—Na2−116.94 (15)
C15—S2—O4—Na1128.50 (16)O6ii—Na3—O3i—S1i162.96 (13)
C15—S2—O4—Na3i−107.60 (15)O3i—Na3—O7i—S3i−168.2 (4)
O5—S2—O6—Na2i−55.7 (2)O3i—Na3—O7i—Na2i0.56 (14)
O5—S2—O6—Na3i−135.54 (12)O3i—Na3—O7i—Na2125.21 (11)
O6—S2—O5—Na254.0 (2)O7i—Na3—O3i—S1i1.22 (17)
O5—S2—C15—C16−116.2 (3)O3i—Na3—O8—S3105.3 (2)
O5—S2—C15—C2061.9 (3)O3i—Na3—O8—Na2−168.06 (7)
C15—S2—O5—Na2170.82 (19)O8—Na3—O3i—S1i95.22 (11)
O6—S2—C15—C165.9 (3)O3i—Na3—O14—C51148.9 (2)
O6—S2—C15—C20−175.9 (2)O3i—Na3—O14—C5413.3 (2)
C15—S2—O6—Na2i−172.4 (2)O14—Na3—O3i—S1i−95.20 (11)
C15—S2—O6—Na3i107.79 (14)O4ii—Na3—O6ii—S2ii4.63 (8)
O7—S3—O8—Na21.51 (12)O4ii—Na3—O6ii—Na2−140.18 (10)
O7—S3—O8—Na384.2 (2)O6ii—Na3—O4ii—S2ii−4.65 (8)
O8—S3—O7—Na2−1.59 (12)O6ii—Na3—O4ii—Na1ii121.54 (12)
O8—S3—O7—Na2ii−127.76 (10)O4ii—Na3—O7i—S3i10.4 (5)
O8—S3—O7—Na3ii167.1 (4)O4ii—Na3—O7i—Na2i179.09 (10)
O7—S3—O9—Na1ii−120.22 (18)O4ii—Na3—O7i—Na2−56.26 (11)
O7—S3—O9—Na2ii−0.81 (13)O7i—Na3—O4ii—S2ii8.63 (17)
O9—S3—O7—Na2126.91 (10)O7i—Na3—O4ii—Na1ii134.83 (10)
O9—S3—O7—Na2ii0.75 (12)O4ii—Na3—O8—S312.7 (2)
O9—S3—O7—Na3ii−64.4 (5)O4ii—Na3—O8—Na299.38 (7)
O7—S3—C29—C30−97.1 (2)O8—Na3—O4ii—S2ii−82.07 (11)
O7—S3—C29—C3478.2 (2)O8—Na3—O4ii—Na1ii44.13 (10)
C29—S3—O7—Na2−119.11 (14)O4ii—Na3—O14—C51−118.2 (2)
C29—S3—O7—Na2ii114.73 (14)O4ii—Na3—O14—C54106.2 (2)
C29—S3—O7—Na3ii49.6 (5)O14—Na3—O4ii—S2ii100.40 (12)
O8—S3—O9—Na1ii6.8 (2)O14—Na3—O4ii—Na1ii−133.41 (11)
O8—S3—O9—Na2ii126.21 (11)O6ii—Na3—O7i—S3i21.8 (4)
O9—S3—O8—Na2−125.08 (11)O6ii—Na3—O7i—Na2i−169.47 (8)
O9—S3—O8—Na3−42.4 (2)O6ii—Na3—O7i—Na2−44.81 (6)
O8—S3—C29—C30142.9 (2)O7i—Na3—O6ii—S2ii−165.30 (10)
O8—S3—C29—C34−41.7 (2)O7i—Na3—O6ii—Na249.89 (7)
C29—S3—O8—Na2118.33 (12)O6ii—Na3—O8—S3−44.1 (2)
C29—S3—O8—Na3−159.02 (18)O6ii—Na3—O8—Na242.50 (7)
O9—S3—C29—C3020.5 (3)O8—Na3—O6ii—S2ii99.06 (10)
O9—S3—C29—C34−164.1 (2)O8—Na3—O6ii—Na2−45.75 (7)
C29—S3—O9—Na1ii124.88 (19)O6ii—Na3—O14—C51−63.2 (2)
C29—S3—O9—Na2ii−115.70 (13)O6ii—Na3—O14—C54161.2 (2)
O1—Na1—O4—S2−62.5 (2)O14—Na3—O6ii—S2ii−70.85 (11)
O1—Na1—O4—Na3i−177.90 (14)O14—Na3—O6ii—Na2144.33 (8)
O4—Na1—O1—S180.1 (2)O7i—Na3—O8—S3−119.5 (2)
O1—Na1—O9i—S3i−171.62 (17)O7i—Na3—O8—Na2−32.89 (7)
O1—Na1—O9i—Na269.27 (10)O8—Na3—O7i—S3i98.7 (4)
O9i—Na1—O1—S1−33.09 (15)O8—Na3—O7i—Na2i−92.61 (8)
O1—Na1—O10—C43−44.4 (3)O8—Na3—O7i—Na232.05 (7)
O1—Na1—O10—C46139.5 (2)O7i—Na3—O14—C5113.8 (2)
O10—Na1—O1—S1−125.51 (13)O7i—Na3—O14—C54−121.8 (2)
O1—Na1—O12—C47157.4 (2)O14—Na3—O7i—S3i−75.4 (5)
O1—Na1—O12—C50−12.4 (3)O14—Na3—O7i—Na2i93.38 (8)
O12—Na1—O1—S1149.23 (14)O14—Na3—O7i—Na2−141.96 (8)
O4—Na1—O9i—S3i39.3 (2)O8—Na3—O14—C51−131.7 (5)
O4—Na1—O9i—Na2−79.82 (9)O8—Na3—O14—C5492.8 (5)
O9i—Na1—O4—S255.36 (14)O14—Na3—O8—S326.1 (6)
O9i—Na1—O4—Na3i−60.09 (11)O14—Na3—O8—Na2112.8 (5)
O4—Na1—O10—C43119.3 (3)Na1—O10—C43—C44127.6 (3)
O4—Na1—O10—C46−56.9 (2)Na1—O10—C46—C45−125.2 (2)
O10—Na1—O4—S2147.83 (13)C43—O10—C46—C4557.9 (4)
O10—Na1—O4—Na3i32.39 (14)C46—O10—C43—C44−55.8 (4)
O4—Na1—O12—C47−54.4 (2)C44—O11—C45—C4654.0 (4)
O4—Na1—O12—C50135.8 (3)C45—O11—C44—C43−53.0 (4)
O12—Na1—O4—S2−132.32 (15)Na1—O12—C47—C48136.3 (3)
O12—Na1—O4—Na3i112.24 (11)Na1—O12—C50—C49−138.0 (3)
O9i—Na1—O10—C43−150.2 (3)C47—O12—C50—C4951.9 (4)
O9i—Na1—O10—C4633.7 (2)C50—O12—C47—C48−52.0 (4)
O10—Na1—O9i—S3i−81.7 (2)C48—O13—C49—C5051.0 (4)
O10—Na1—O9i—Na2159.15 (9)C49—O13—C48—C47−50.5 (4)
O9i—Na1—O12—C47−11.1 (6)Na3—O14—C51—C52160.1 (2)
O9i—Na1—O12—C50179.1 (4)Na3—O14—C54—C53−163.4 (2)
O12—Na1—O9i—S3i−3.6 (6)C51—O14—C54—C5358.9 (3)
O12—Na1—O9i—Na2−122.7 (5)C54—O14—C51—C52−58.7 (3)
O10—Na1—O12—C4767.8 (2)C52—O15—C53—C5457.6 (3)
O10—Na1—O12—C50−102.0 (3)C53—O15—C52—C51−57.2 (3)
O12—Na1—O10—C4340.9 (3)N2—N1—C4—C3172.3 (3)
O12—Na1—O10—C46−135.3 (2)N2—N1—C4—C5−10.1 (5)
O2—Na2—O5—S2116.5 (2)C4—N1—N2—C7177.9 (3)
O5—Na2—O2—S1−107.2 (3)N1—N2—C7—C8−9.9 (5)
O5—Na2—O2—Na3ii95.84 (10)N1—N2—C7—C12171.5 (3)
O2—Na2—O6ii—S2ii96.0 (2)C13—N3—C10—C94.8 (5)
O2—Na2—O6ii—Na3179.03 (8)C13—N3—C10—C11−178.0 (3)
O6ii—Na2—O2—S177.6 (3)C14—N3—C10—C9173.0 (3)
O6ii—Na2—O2—Na3ii−79.37 (10)C14—N3—C10—C11−9.8 (5)
O2—Na2—O7—S3172.89 (11)N5—N4—C18—C17−179.3 (3)
O2—Na2—O7—Na2ii−87.92 (11)N5—N4—C18—C19−0.3 (5)
O2—Na2—O7—Na3ii−4.16 (8)C18—N4—N5—C21178.7 (3)
O7—Na2—O2—S1161.4 (3)N4—N5—C21—C220.1 (5)
O7—Na2—O2—Na3ii4.37 (8)N4—N5—C21—C26178.3 (3)
O2—Na2—O7i—S3i−14.05 (16)C27—N6—C24—C232.5 (6)
O2—Na2—O7i—Na2i−115.59 (13)C27—N6—C24—C25−178.0 (3)
O2—Na2—O7i—Na3152.02 (12)C28—N6—C24—C23−174.3 (3)
O7i—Na2—O2—S1−12.2 (4)C28—N6—C24—C255.2 (5)
O7i—Na2—O2—Na3ii−169.15 (9)N8—N7—C32—C31157.9 (3)
O2—Na2—O8—S3−12.78 (17)N8—N7—C32—C33−23.8 (4)
O2—Na2—O8—Na3−151.88 (12)C32—N7—N8—C35−179.6 (3)
O8—Na2—O2—S1171.4 (2)N7—N8—C35—C360.6 (5)
O8—Na2—O2—Na3ii14.43 (16)N7—N8—C35—C40−177.1 (3)
O2—Na2—O9i—S3i171.19 (11)C41—N9—C38—C37−16.5 (5)
O2—Na2—O9i—Na1−45.06 (9)C41—N9—C38—C39164.7 (3)
O9i—Na2—O2—S1−23.5 (3)C42—N9—C38—C37−175.4 (3)
O9i—Na2—O2—Na3ii179.51 (9)C42—N9—C38—C395.8 (5)
O5—Na2—O6ii—S2ii−70.6 (4)S1—C1—C2—C3−178.2 (2)
O5—Na2—O6ii—Na312.4 (2)S1—C1—C6—C5179.2 (2)
O6ii—Na2—O5—S2−76.2 (3)C2—C1—C6—C5−1.1 (5)
O5—Na2—O7—S381.09 (10)C6—C1—C2—C32.2 (5)
O5—Na2—O7—Na2ii−179.71 (11)C1—C2—C3—C4−1.4 (5)
O5—Na2—O7—Na3ii−95.95 (8)C2—C3—C4—N1177.4 (3)
O7—Na2—O5—S2−163.1 (2)C2—C3—C4—C5−0.3 (5)
O5—Na2—O7i—S3i81.02 (10)N1—C4—C5—C6−176.2 (3)
O5—Na2—O7i—Na2i−20.52 (12)C3—C4—C5—C61.4 (5)
O5—Na2—O7i—Na3−112.91 (8)C4—C5—C6—C1−0.6 (5)
O7i—Na2—O5—S2−20.6 (2)N2—C7—C8—C9179.2 (3)
O5—Na2—O8—S3−97.88 (10)N2—C7—C12—C11−178.4 (3)
O5—Na2—O8—Na3123.02 (8)C8—C7—C12—C112.8 (5)
O8—Na2—O5—S2−106.3 (2)C12—C7—C8—C9−2.1 (5)
O5—Na2—O9i—S3i−95.83 (11)C7—C8—C9—C10−0.9 (5)
O5—Na2—O9i—Na147.92 (9)C8—C9—C10—N3−179.6 (3)
O9i—Na2—O5—S235.0 (2)C8—C9—C10—C113.1 (5)
O6ii—Na2—O7—S3−77.69 (10)N3—C10—C11—C12−179.7 (3)
O6ii—Na2—O7—Na2ii21.50 (11)C9—C10—C11—C12−2.4 (5)
O6ii—Na2—O7—Na3ii105.26 (8)C10—C11—C12—C7−0.6 (5)
O7—Na2—O6ii—S2ii17.2 (2)S2—C15—C16—C17−179.5 (2)
O7—Na2—O6ii—Na3100.18 (7)S2—C15—C20—C19179.4 (2)
O6ii—Na2—O7i—S3i−116.86 (10)C16—C15—C20—C19−2.4 (5)
O6ii—Na2—O7i—Na2i141.60 (11)C20—C15—C16—C172.3 (5)
O6ii—Na2—O7i—Na349.21 (7)C15—C16—C17—C18−0.3 (5)
O7i—Na2—O6ii—S2ii−128.6 (2)C16—C17—C18—N4177.4 (3)
O7i—Na2—O6ii—Na3−45.63 (6)C16—C17—C18—C19−1.7 (6)
O6ii—Na2—O8—S392.78 (10)N4—C18—C19—C20−177.3 (3)
O6ii—Na2—O8—Na3−46.31 (8)C17—C18—C19—C201.6 (6)
O8—Na2—O6ii—S2ii−40.2 (2)C18—C19—C20—C150.5 (5)
O8—Na2—O6ii—Na342.83 (6)N5—C21—C22—C23179.3 (4)
O6ii—Na2—O9i—S3i63.89 (11)N5—C21—C26—C25−178.8 (3)
O6ii—Na2—O9i—Na1−152.36 (9)C22—C21—C26—C25−0.4 (6)
O9i—Na2—O6ii—S2ii−178.4 (2)C26—C21—C22—C231.2 (6)
O9i—Na2—O6ii—Na3−95.42 (8)C21—C22—C23—C24−1.3 (6)
O7—Na2—O7i—S3i176.44 (11)C22—C23—C24—N6−179.8 (3)
O7—Na2—O7i—Na2i74.90 (17)C22—C23—C24—C250.7 (6)
O7—Na2—O7i—Na3−17.49 (14)N6—C24—C25—C26−179.5 (3)
O7i—Na2—O7—S3−14.36 (18)C23—C24—C25—C26−0.0 (5)
O7i—Na2—O7—Na2ii84.84 (16)C24—C25—C26—C21−0.1 (5)
O7i—Na2—O7—Na3ii168.60 (11)S3—C29—C30—C31173.3 (2)
O7—Na2—O8—S3−1.00 (8)S3—C29—C34—C33−172.0 (2)
O7—Na2—O8—Na3−140.09 (9)C30—C29—C34—C333.3 (4)
O8—Na2—O7—S31.00 (8)C34—C29—C30—C31−2.0 (5)
O8—Na2—O7—Na2ii100.19 (11)C29—C30—C31—C32−2.5 (5)
O8—Na2—O7—Na3ii−176.05 (9)C30—C31—C32—N7−176.1 (3)
O7—Na2—O9i—S3i−173.6 (2)C30—C31—C32—C335.5 (5)
O7—Na2—O9i—Na1−29.9 (3)N7—C32—C33—C34177.6 (3)
O9i—Na2—O7—S3157.6 (2)C31—C32—C33—C34−4.2 (5)
O9i—Na2—O7—Na2ii−103.2 (2)C32—C33—C34—C29−0.2 (4)
O9i—Na2—O7—Na3ii−19.4 (2)N8—C35—C36—C37−177.9 (3)
O7i—Na2—O8—S3169.67 (9)N8—C35—C40—C39178.0 (3)
O7i—Na2—O8—Na330.57 (7)C36—C35—C40—C390.2 (4)
O8—Na2—O7i—S3i163.50 (9)C40—C35—C36—C37−0.3 (5)
O8—Na2—O7i—Na2i61.96 (11)C35—C36—C37—C380.4 (6)
O8—Na2—O7i—Na3−30.42 (6)C36—C37—C38—N9−179.3 (3)
O7i—Na2—O9i—S3i0.50 (8)C36—C37—C38—C39−0.5 (5)
O7i—Na2—O9i—Na1144.25 (10)N9—C38—C39—C40179.2 (3)
O9i—Na2—O7i—S3i−0.50 (8)C37—C38—C39—C400.4 (5)
O9i—Na2—O7i—Na2i−102.04 (12)C38—C39—C40—C35−0.2 (5)
O9i—Na2—O7i—Na3165.58 (9)O10—C43—C44—O1154.7 (5)
O8—Na2—O9i—S3i−24.36 (16)O11—C45—C46—O10−58.4 (4)
O8—Na2—O9i—Na1119.39 (12)O12—C47—C48—O1352.9 (5)
O9i—Na2—O8—S3−169.85 (11)O13—C49—C50—O12−52.9 (5)
O9i—Na2—O8—Na351.05 (13)O14—C51—C52—O1558.4 (3)
O2i—Na3—O3i—S1i−2.78 (9)O15—C53—C54—O14−59.5 (4)
O3i—Na3—O2i—S1i2.82 (9)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2280).

References

  • Burke, N. J., Burrows, A. D., Mahon, M. F. & Teat, S. J. (2004). CrystEngComm, 6, 429–437.
  • Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst.38, 381–388.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Hanson, A. W. (1973). Acta Cryst. B29, 454–460.
  • Herbst, W. & Hunger, K. (2004). Industrial Organic Pigments, pp. 183–419. Weinheim: VCH.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Kennedy, A. R., Kirkhouse, J. B. A., McCarney, K. M., Puissegur, O., Smith, W. E., Staunton, E., Teat, S. J., Cherryman, J. C. & James, R. (2004). Chem. Eur. J.10, 4606–4615. [PubMed]
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC and Rigaku (2006). CrystalStructure Rigaku/MSC Inc., The Woodlands, Texas, USA and Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography