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Acta Cryst. (2007). E63, m2316    [ doi:10.1107/S1600536807038305 ]

Diaqua[2,6-bis(2,6-diethyl-4-sulfonatophenyl)-3,5-dimethyl-2,6-diazoniaheptan-4-ido]sodium(I)

X. Guo, Q. Wang, K. Harms and H. Sun

Abstract top

The title compound, [Na(C25H33N2O6S2)(H2O)2], was obtained as a product of the reaction of sodium 4-amino-3,5-diethylbenzenesulfonate with acetylacetone in the presence of hydrochloric acid in methanol. The molecule lies on a crystallographic twofold rotation axis and is a `triple' internal salt which has three positive charge centers and three negative charge centers. The Na atom has a tetrahedral coordination geometry. The O atoms of the sulfonate groups are disordered over two positions with site occupancy factors of 0.87 and 0.13; the methyl groups of the ethyl substituents are disordered equally over two positions.

Comment top

In the title compound both N atoms are protonated, rather than the sulfonate groups. In the title molecule (Fig. 1) the sodium atom is coordinated in a distorted tetrahedral geometry by two O atoms of two sulfonate groups and two water molecules. There is an intermolecular hydrogen bond between the N—H group and an O atom of a sulfonate group. The O atoms of the –SO3 groups are disordered over two sites as are the terminal –CH3 groups of the ethyl substituents.

Similar crystal structures have been reported in the literature e.g. 2-N-phenylamino-4-N-phenylimino-2-pentene hydrochloride and 4-(2,4,6-trimethylphenyliminio)-2-(2,4,6-trimethylphenylamino) pent-2-ene)iodide tetrachloro-arsenate (Brownstein et al., 1983; Lesikar & Richards, 2006). The bond lengths and angles of these compounds are similar to those in the title compound. There is also intermolecular hydrogen bonding in 2-N-phenylamino-4-N-phenylimino-2-pentene hydrochloride.

Related literature top

Related crystal structures of β-diimine Schiff base compounds have been reported (Brownstein et al., 1983; Lesikar & Richards, 2006).

Experimental top

1.7 ml concentrated hydrochloric acid was added to a anhydrous methanol solution of 5.02 g (20 mmol) 3, 5-diethyl-4-amido-benzenesulfonate sodium and 1.05 g (10.5 mmol) acetyl acetone and refluxed for 6 days. A white precipitate was observed and filtered off and then washed with anhydrous methanol and a white product was obtained. This product was dissolved in methanol, and recrystallized at 258 K for 5 days, the title compound was obtained as colorless crystals (Yield 53%).

Refinement top

The H atoms on the hydrate ligands were not visible in the difference Fourier maps and have not been included in the refinement although they are included in the molecular formula. All the other H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C). The O atoms of the unique –SO3 group are disordered over two sites with refined occupancies 0.869 (11) and 0.131 (11). In addition the methyl groups of the ethyl substituents are also disordered with equall occupancies for both components.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure with atom labels and 30% probability displacement ellipsoids for non-H atoms. Only selected H atoms are shown. The disorder is not shown.
Diaqua[2,6-bis(2,6-diethyl-4-sulfonatophenyl)-3,5-dimethyl-2,6-\ diazoniaheptan-4-ido]sodium(I) top
Crystal data top
[Na(C25H33N2O6S2)(H2O)2]Z = 8
Mr = 580.64F000 = 2432
Tetragonal, I41/aDx = 1.258 Mg m−3
Hall symbol: -I 4adMo Kα radiation
λ = 0.71073 Å
a = 12.1767 (3) ÅCell parameters from 3063 reflections
b = 12.1767 (3) Åθ = 3.1–20.4º
c = 41.055 (3) ŵ = 0.24 mm−1
α = 90ºT = 193 (2) K
β = 90ºBlock, colourless
γ = 90º0.22 × 0.18 × 0.11 mm
V = 6087.2 (4) Å3
Data collection top
Bruker SMART CCD
diffractometer		2699 independent reflections
Radiation source: fine-focus sealed tube1517 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.108
T = 193(2) Kθmax = 25.0º
ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.950, Tmax = 0.975k = −10→13
20660 measured reflectionsl = −48→48
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.064  w = 1/[σ2(Fo2) + (0.102P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.186(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.38 e Å−3
2699 reflectionsΔρmin = −0.31 e Å−3
220 parametersExtinction correction: none
81 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Crystal data top
[Na(C25H33N2O6S2)(H2O)2]γ = 90º
Mr = 580.64V = 6087.2 (4) Å3
Tetragonal, I41/aZ = 8
a = 12.1767 (3) ÅMo Kα
b = 12.1767 (3) ŵ = 0.24 mm−1
c = 41.055 (3) ÅT = 193 (2) K
α = 90º0.22 × 0.18 × 0.11 mm
β = 90º
Data collection top
Bruker SMART CCD
diffractometer		2699 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1517 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.975Rint = 0.108
20660 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.186Δρmax = 0.38 e Å−3
S = 1.01Δρmin = −0.31 e Å−3
2699 reflectionsAbsolute structure: ?
220 parametersFlack parameter: ?
81 restraintsRogers parameter: ?
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 > 2sigma(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
xyzUiso*/UeqOcc. (<1)
C10.5271 (3)0.0576 (3)0.66152 (8)0.0504 (9)
C20.4370 (3)0.1229 (3)0.65483 (9)0.0515 (9)
H20.40370.16340.67200.062*
C30.3946 (3)0.1304 (3)0.62371 (9)0.0502 (9)
C40.4459 (3)0.0701 (3)0.59912 (8)0.0503 (9)
C50.5358 (3)0.0018 (3)0.60522 (8)0.0534 (9)
C60.5743 (3)−0.0025 (3)0.63688 (8)0.0555 (10)
H60.6353−0.04830.64180.067*
C70.2966 (3)0.2026 (3)0.61710 (10)0.0623 (10)
H7A0.28920.25590.63520.075*
H7B0.31030.24480.59690.075*
C80.1899 (4)0.1414 (5)0.61348 (17)0.118 (2)
H8A0.20000.07960.59850.178*
H8B0.13370.19100.60480.178*
H8C0.16640.11380.63480.178*
C90.5914 (3)−0.0633 (3)0.57863 (9)0.0679 (11)
H9A0.6275−0.12820.58850.082*0.50
H9B0.5349−0.09020.56320.082*0.50
H9C0.5855−0.02510.55800.082*0.50
H9D0.6687−0.07290.58370.082*0.50
C100.6760 (6)0.0018 (6)0.55996 (17)0.0545 (19)0.50
H10A0.7139−0.04660.54450.082*0.50
H10B0.72950.03300.57520.082*0.50
H10C0.63960.06120.54800.082*0.50
C10A0.5352 (10)−0.1738 (10)0.5755 (3)0.125 (4)0.50
H10D0.4582−0.16290.56930.188*0.50
H10E0.5386−0.21240.59650.188*0.50
H10F0.5723−0.21760.55880.188*0.50
C110.4461 (3)0.1622 (3)0.54605 (9)0.0606 (10)
C120.4170 (4)0.1490 (4)0.51115 (9)0.0894 (15)
H12A0.48400.13660.49840.134*
H12B0.38030.21560.50340.134*
H12C0.36760.08600.50860.134*
C130.50000.25000.55988 (14)0.0584 (14)
N10.4111 (3)0.0809 (3)0.56575 (8)0.0583 (9)
O40.3487 (4)0.2510 (8)0.78203 (14)0.262 (4)
Na10.50000.25000.74867 (6)0.0922 (8)
S10.58590 (9)0.05700 (8)0.70120 (2)0.0612 (4)
O10.4967 (4)0.0733 (5)0.72347 (10)0.0889 (18)0.869 (11)
O20.6390 (5)−0.0470 (4)0.70533 (9)0.0819 (16)0.869 (11)
O30.6590 (6)0.1505 (5)0.70159 (15)0.119 (2)0.869 (11)
O2A0.6973 (18)0.023 (4)0.6994 (7)0.099 (14)0.131 (11)
O1A0.506 (2)0.001 (4)0.7204 (9)0.117 (15)0.131 (11)
O3A0.590 (3)0.1683 (14)0.7130 (8)0.095 (9)0.131 (11)
H10.377 (3)0.022 (3)0.5607 (9)0.067 (13)*
H130.50000.25000.5828 (12)0.048 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (2)0.045 (2)0.061 (2)−0.0081 (16)−0.0005 (17)0.0017 (17)
C20.050 (2)0.047 (2)0.057 (2)−0.0037 (17)0.0048 (18)−0.0015 (17)
C30.045 (2)0.041 (2)0.065 (2)−0.0067 (15)−0.0019 (18)0.0014 (17)
C40.052 (2)0.044 (2)0.055 (2)−0.0092 (17)−0.0070 (18)−0.0011 (17)
C50.052 (2)0.048 (2)0.060 (2)0.0011 (18)−0.0046 (18)−0.0016 (18)
C60.051 (2)0.056 (2)0.060 (2)0.0065 (18)−0.0029 (18)−0.0007 (18)
C70.057 (2)0.058 (2)0.073 (2)0.0061 (19)−0.006 (2)−0.002 (2)
C80.061 (3)0.095 (4)0.200 (6)0.003 (3)−0.011 (4)0.006 (4)
C90.075 (3)0.069 (3)0.060 (2)0.011 (2)−0.010 (2)−0.017 (2)
C100.042 (4)0.072 (5)0.049 (4)0.016 (4)0.002 (3)−0.012 (4)
C10A0.124 (10)0.146 (11)0.106 (8)0.018 (8)−0.003 (7)−0.039 (8)
C110.067 (3)0.058 (3)0.057 (2)0.002 (2)−0.007 (2)−0.003 (2)
C120.125 (4)0.085 (3)0.058 (3)−0.008 (3)−0.023 (3)−0.003 (2)
C130.074 (4)0.053 (4)0.048 (3)−0.003 (3)0.0000.000
N10.066 (2)0.048 (2)0.061 (2)−0.0042 (17)−0.0150 (16)−0.0086 (17)
O40.124 (4)0.491 (12)0.171 (5)−0.108 (6)0.038 (3)0.070 (6)
Na10.1482 (18)0.099 (2)0.0908 (17)−0.0076 (14)0.0000.000
S10.0625 (7)0.0653 (8)0.0559 (6)−0.0015 (5)−0.0058 (5)−0.0010 (5)
O10.087 (3)0.120 (4)0.059 (2)0.034 (3)0.005 (2)−0.008 (3)
O20.087 (4)0.096 (3)0.063 (2)0.038 (3)−0.009 (2)0.001 (2)
O30.125 (5)0.136 (4)0.096 (4)−0.079 (4)−0.045 (3)0.026 (3)
O2A0.040 (16)0.18 (4)0.078 (16)0.064 (18)−0.010 (13)−0.05 (2)
O1A0.045 (17)0.17 (3)0.14 (3)−0.05 (2)−0.006 (15)0.09 (3)
O3A0.14 (2)0.065 (15)0.081 (17)−0.075 (15)−0.050 (16)0.017 (12)
Geometric parameters (Å, °) top
C1—C61.374 (5)C10A—H10E0.9800
C1—C21.382 (5)C10A—H10F0.9800
C1—S11.779 (4)C11—N11.347 (5)
C2—C31.381 (5)C11—C131.377 (4)
C2—H20.9500C11—C121.484 (5)
C3—C41.396 (5)C12—H12A0.9800
C3—C71.507 (5)C12—H12B0.9800
C4—C51.397 (5)C12—H12C0.9800
C4—N11.440 (4)C13—C11i1.377 (4)
C5—C61.383 (5)C13—H130.94 (4)
C5—C91.509 (5)N1—H10.85 (4)
C6—H60.9500O4—Na12.295 (5)
C7—C81.505 (6)Na1—O3Ai2.08 (4)
C7—H7A0.9900Na1—O3A2.08 (4)
C7—H7B0.9900Na1—O4i2.295 (5)
C8—H8A0.9800Na1—O12.387 (6)
C8—H8B0.9800Na1—O1i2.387 (6)
C8—H8C0.9800Na1—O3i2.992 (9)
C9—C101.509 (8)Na1—O32.992 (9)
C9—C10A1.516 (13)Na1—S13.2274 (19)
C9—H9A0.9900Na1—S1i3.2274 (19)
C9—H9B0.9900S1—O2A1.422 (13)
C9—H9C0.9700S1—O1A1.430 (14)
C9—H9D0.9700S1—O21.431 (4)
C10—H10A0.9800S1—O11.433 (4)
C10—H10B0.9800S1—O3A1.439 (15)
C10—H10C0.9800S1—O31.445 (4)
C10A—H10D0.9800
C6—C1—C2119.5 (3)C11i—C13—H13114.4 (3)
C6—C1—S1120.2 (3)C11—N1—C4123.1 (3)
C2—C1—S1120.2 (3)C11—N1—H1129 (3)
C3—C2—C1121.2 (3)C4—N1—H1107 (3)
C3—C2—H2119.4O3Ai—Na1—O3A90.6 (16)
C1—C2—H2119.4O3Ai—Na1—O489.7 (9)
C2—C3—C4117.8 (3)O3A—Na1—O4147.7 (9)
C2—C3—C7120.1 (3)O3Ai—Na1—O4i147.7 (9)
C4—C3—C7122.1 (3)O3A—Na1—O4i89.7 (9)
C3—C4—C5122.3 (3)O4—Na1—O4i106.7 (3)
C3—C4—N1120.5 (3)O3Ai—Na1—O196.7 (8)
C5—C4—N1117.1 (3)O3A—Na1—O143.4 (8)
C6—C5—C4117.1 (3)O4—Na1—O1104.5 (3)
C6—C5—C9120.5 (3)O4i—Na1—O1105.5 (3)
C4—C5—C9122.3 (3)O3Ai—Na1—O1i43.4 (8)
C1—C6—C5122.0 (3)O3A—Na1—O1i96.7 (8)
C1—C6—H6119.0O4—Na1—O1i105.5 (3)
C5—C6—H6119.0O4i—Na1—O1i104.5 (3)
C8—C7—C3114.4 (3)O1—Na1—O1i128.6 (3)
C8—C7—H7A108.7O3Ai—Na1—O3i8.7 (9)
C3—C7—H7A108.7O3A—Na1—O3i94.6 (8)
C8—C7—H7B108.7O4—Na1—O3i82.2 (2)
C3—C7—H7B108.7O4i—Na1—O3i155.1 (3)
H7A—C7—H7B107.6O1—Na1—O3i94.26 (17)
C7—C8—H8A109.5O1i—Na1—O3i50.64 (15)
C7—C8—H8B109.5O3Ai—Na1—O394.6 (8)
H8A—C8—H8B109.5O3A—Na1—O38.7 (9)
C7—C8—H8C109.5O4—Na1—O3155.1 (3)
H8A—C8—H8C109.5O4i—Na1—O382.2 (2)
H8B—C8—H8C109.5O1—Na1—O350.64 (15)
C10—C9—C5113.4 (4)O1i—Na1—O394.26 (17)
C10—C9—C10A137.1 (6)O3i—Na1—O399.5 (2)
C5—C9—C10A108.9 (5)O3Ai—Na1—S195.4 (8)
C10—C9—H9A108.9O3A—Na1—S119.4 (8)
C5—C9—H9A108.9O4—Na1—S1128.6 (2)
C10A—C9—H9A61.7O4i—Na1—S195.5 (2)
C10—C9—H9B108.9O1—Na1—S124.15 (13)
C5—C9—H9B108.9O1i—Na1—S1112.89 (15)
C10A—C9—H9B48.6O3i—Na1—S196.57 (13)
H9A—C9—H9B107.7O3—Na1—S126.52 (8)
C10—C9—H9C49.8O3Ai—Na1—S1i19.4 (8)
C5—C9—H9C110.3O3A—Na1—S1i95.4 (8)
C10A—C9—H9C108.6O4—Na1—S1i95.5 (2)
H9A—C9—H9C140.5O4i—Na1—S1i128.6 (2)
H9B—C9—H9C63.2O1—Na1—S1i112.89 (15)
C10—C9—H9D60.7O1i—Na1—S1i24.15 (13)
C5—C9—H9D110.1O3i—Na1—S1i26.52 (8)
C10A—C9—H9D110.4O3—Na1—S1i96.57 (13)
H9A—C9—H9D52.2S1—Na1—S1i105.70 (8)
H9B—C9—H9D140.4O2A—S1—O1A123 (2)
H9C—C9—H9D108.5O2A—S1—O247 (2)
C9—C10—H9C40.0O1A—S1—O280 (2)
C9—C10—H9D39.3O2A—S1—O1142.8 (14)
H9C—C10—H9D78.1O1A—S1—O136 (2)
C9—C10—H10A109.5O2—S1—O1112.9 (3)
H9C—C10—H10A103.5O2A—S1—O3A105.1 (19)
H9D—C10—H10A95.4O1A—S1—O3A107 (2)
C9—C10—H10B109.5O2—S1—O3A141.0 (13)
H9C—C10—H10B142.3O1—S1—O3A71.5 (17)
H9D—C10—H10B81.0O2A—S1—O369 (2)
C9—C10—H10C109.5O1A—S1—O3142 (2)
H9C—C10—H10C75.1O2—S1—O3114.7 (3)
H9D—C10—H10C146.8O1—S1—O3110.5 (4)
C9—C10A—H10D109.5O3A—S1—O339.9 (15)
C9—C10A—H10E109.5O2A—S1—C1109.8 (11)
H10D—C10A—H10E109.5O1A—S1—C1103.4 (15)
C9—C10A—H10F109.5O2—S1—C1107.1 (2)
H10D—C10A—H10F109.5O1—S1—C1106.2 (2)
H10E—C10A—H10F109.5O3A—S1—C1108.5 (12)
N1—C11—C13118.2 (4)O3—S1—C1104.8 (2)
N1—C11—C12115.1 (4)O2A—S1—Na1123.7 (14)
C13—C11—C12126.6 (4)O1A—S1—Na178 (3)
C11—C12—H12A109.5O2—S1—Na1135.95 (16)
C11—C12—H12B109.5O1—S1—Na143.0 (3)
H12A—C12—H12B109.5O3A—S1—Na128.8 (17)
C11—C12—H12C109.5O3—S1—Na167.6 (4)
H12A—C12—H12C109.5C1—S1—Na1114.80 (13)
H12B—C12—H12C109.5S1—O1—Na1112.9 (4)
C11—C13—C11i131.3 (5)S1—O3—Na185.9 (4)
C11—C13—H13114.4 (3)S1—O3A—Na1132 (2)
C6—C1—C2—C3−1.1 (5)O4i—Na1—S1—O1116.1 (4)
S1—C1—C2—C3175.5 (3)O1i—Na1—S1—O1−135.6 (3)
C1—C2—C3—C4−0.2 (5)O3i—Na1—S1—O1−85.7 (3)
C1—C2—C3—C7−179.8 (3)O3—Na1—S1—O1176.1 (4)
C2—C3—C4—C51.4 (5)S1i—Na1—S1—O1−111.1 (3)
C7—C3—C4—C5−179.0 (3)O3Ai—Na1—S1—O3A76 (3)
C2—C3—C4—N1−175.1 (3)O4—Na1—S1—O3A170 (3)
C7—C3—C4—N14.4 (5)O4i—Na1—S1—O3A−73 (3)
C3—C4—C5—C6−1.2 (5)O1—Na1—S1—O3A171 (3)
N1—C4—C5—C6175.4 (3)O1i—Na1—S1—O3A35 (3)
C3—C4—C5—C9−179.9 (3)O3i—Na1—S1—O3A85 (3)
N1—C4—C5—C9−3.2 (5)O3—Na1—S1—O3A−13 (3)
C2—C1—C6—C51.2 (5)S1i—Na1—S1—O3A60 (3)
S1—C1—C6—C5−175.4 (3)O3Ai—Na1—S1—O389.5 (9)
C4—C5—C6—C1−0.1 (5)O3A—Na1—S1—O313 (3)
C9—C5—C6—C1178.6 (4)O4—Na1—S1—O3−176.6 (3)
C2—C3—C7—C8−102.8 (5)O4i—Na1—S1—O3−60.0 (3)
C4—C3—C7—C877.7 (5)O1—Na1—S1—O3−176.1 (4)
C6—C5—C9—C10−94.6 (5)O1i—Na1—S1—O348.3 (3)
C4—C5—C9—C1084.0 (5)O3i—Na1—S1—O398.1 (3)
C6—C5—C9—C10A92.4 (6)S1i—Na1—S1—O372.7 (2)
C4—C5—C9—C10A−89.0 (6)O3Ai—Na1—S1—C1−7.0 (9)
N1—C11—C13—C11i172.5 (4)O3A—Na1—S1—C1−83 (3)
C12—C11—C13—C11i−10.5 (3)O4—Na1—S1—C186.9 (3)
C13—C11—N1—C4−12.9 (5)O4i—Na1—S1—C1−156.5 (2)
C12—C11—N1—C4169.8 (4)O1—Na1—S1—C187.4 (3)
C3—C4—N1—C1183.0 (5)O1i—Na1—S1—C1−48.26 (18)
C5—C4—N1—C11−93.7 (4)O3i—Na1—S1—C11.62 (15)
C6—C1—S1—O2A20 (3)O3—Na1—S1—C1−96.5 (3)
C2—C1—S1—O2A−157 (3)S1i—Na1—S1—C1−23.80 (12)
C6—C1—S1—O1A−113 (2)O2A—S1—O1—Na186 (3)
C2—C1—S1—O1A71 (2)O1A—S1—O1—Na1160 (3)
C6—C1—S1—O2−29.4 (4)O2—S1—O1—Na1133.7 (3)
C2—C1—S1—O2154.1 (4)O3A—S1—O1—Na1−4.7 (13)
C6—C1—S1—O1−150.2 (4)O3—S1—O1—Na13.8 (4)
C2—C1—S1—O133.2 (4)C1—S1—O1—Na1−109.2 (2)
C6—C1—S1—O3A134.3 (19)O3Ai—Na1—O1—S188.2 (10)
C2—C1—S1—O3A−42.2 (19)O3A—Na1—O1—S14.4 (12)
C6—C1—S1—O392.8 (5)O4—Na1—O1—S1179.6 (3)
C2—C1—S1—O3−83.7 (5)O4i—Na1—O1—S1−68.1 (3)
C6—C1—S1—Na1164.6 (3)O1i—Na1—O1—S155.6 (2)
C2—C1—S1—Na1−11.9 (3)O3i—Na1—O1—S196.6 (3)
O3Ai—Na1—S1—O2A132 (3)O3—Na1—O1—S1−2.2 (2)
O3A—Na1—S1—O2A56 (3)S1i—Na1—O1—S177.1 (3)
O4—Na1—S1—O2A−134 (3)O2A—S1—O3—Na1−143.0 (13)
O4i—Na1—S1—O2A−17 (3)O1A—S1—O3—Na1−26 (3)
O1—Na1—S1—O2A−134 (3)O2—S1—O3—Na1−131.8 (2)
O1i—Na1—S1—O2A91 (3)O1—S1—O3—Na1−2.8 (3)
O3i—Na1—S1—O2A141 (3)O3A—S1—O3—Na19.8 (19)
O3—Na1—S1—O2A43 (3)C1—S1—O3—Na1111.13 (16)
S1i—Na1—S1—O2A115 (3)O3Ai—Na1—O3—S1−92.9 (9)
O3Ai—Na1—S1—O1A−106.4 (16)O3A—Na1—O3—S1−30 (5)
O3A—Na1—S1—O1A177 (3)O4—Na1—O3—S16.3 (6)
O4—Na1—S1—O1A−12.5 (14)O4i—Na1—O3—S1119.5 (3)
O4i—Na1—S1—O1A104.1 (14)O1—Na1—O3—S12.0 (2)
O1—Na1—S1—O1A−12.0 (15)O1i—Na1—O3—S1−136.4 (3)
O1i—Na1—S1—O1A−147.6 (14)O3i—Na1—O3—S1−85.7 (2)
O3i—Na1—S1—O1A−97.7 (13)S1i—Na1—O3—S1−112.3 (2)
O3—Na1—S1—O1A164.1 (13)O2A—S1—O3A—Na1−135 (2)
S1i—Na1—S1—O1A−123.1 (13)O1A—S1—O3A—Na1−3(3)
O3Ai—Na1—S1—O2−167.6 (11)O2—S1—O3A—Na1−97 (3)
O3A—Na1—S1—O2116 (3)O1—S1—O3A—Na16.6 (19)
O4—Na1—S1—O2−73.7 (5)O3—S1—O3A—Na1−161 (4)
O4i—Na1—S1—O242.9 (4)C1—S1—O3A—Na1108 (2)
O1—Na1—S1—O2−73.2 (4)O3Ai—Na1—O3A—S1−105 (3)
O1i—Na1—S1—O2151.2 (4)O4—Na1—O3A—S1−14 (4)
O3i—Na1—S1—O2−159.0 (4)O4i—Na1—O3A—S1108 (2)
O3—Na1—S1—O2102.9 (4)O1—Na1—O3A—S1−5.5 (16)
S1i—Na1—S1—O2175.6 (4)O1i—Na1—O3A—S1−148 (2)
O3Ai—Na1—S1—O1−94.4 (10)O3i—Na1—O3A—S1−97 (2)
O3A—Na1—S1—O1−171 (3)O3—Na1—O3A—S1138 (7)
O4—Na1—S1—O1−0.5 (4)S1i—Na1—O3A—S1−123 (2)
Symmetry codes: (i) −x+1, −y+1/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2ii0.85 (4)2.01 (4)2.854 (6)175 (4)
N1—H1···O2Aii0.85 (4)2.08 (5)2.83 (3)148 (4)
Symmetry codes: (ii) −y+1/4, x−3/4, −z+5/4.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.85 (4)2.01 (4)2.854 (6)175 (4)
N1—H1···O2Ai0.85 (4)2.08 (5)2.83 (3)148 (4)
Symmetry codes: (i) −y+1/4, x−3/4, −z+5/4.
Acknowledgements top

This work was supported by the NSFC (Nos. 20572062 and 20372042), by the Doctoral Program of the MOE (Nos. 20050422010 and 20050422011), and by the Deutsche Forschungsgemeinschaft (No. SFB 260).

references
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