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

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

doi:10.1107/S1600536807038305

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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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038305/lh2437sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038305/lh2437Isup2.hkl Contains datablock I

CCDC reference: 660086

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.005 Å
H-atom completeness 90%
Disorder in main residue
R factor = 0.064
wR factor = 0.186
Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Na1
PLAT430_ALERT_2_B Short Inter D...A Contact  O3     ..  O4      ..       2.70 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.108
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom O1A     has ADP max/min Ratio .............       3.60 prola
PLAT213_ALERT_2_C Atom O2A     has ADP max/min Ratio .............       4.00 prola
PLAT213_ALERT_2_C Atom O3A     has ADP max/min Ratio .............       3.60 prola
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.92 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT245_ALERT_2_C U(iso) H9A     Smaller than U(eq) C10A    by ...       0.04 AngSq
PLAT245_ALERT_2_C U(iso) H9B     Smaller than U(eq) C10A    by ...       0.04 AngSq
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  C12    ..  O1A     ..       2.95 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.18 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.00 Deg.
              C9   -C10  -H9C     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.30 Deg.
              C9   -C10  -H9D     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.00 Deg.
              O1A  -S1   -O1      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.90 Deg.
              O3A  -S1   -O3      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.00 Deg.
              O1   -S1   -NA1     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.80 Deg.
              O3A  -S1   -NA1     1.555   1.555   1.555

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C25 H37 N2 Na1 O8 S2
            Atom count from the _atom_site data:  C25 H33 N2 Na1 O8 S2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C25 H37 N2 Na O8 S2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        200.00    200.00    0.00
           H        296.00    264.00   32.00
           N         16.00     16.00    0.00
           Na         8.00      8.00    0.00
           O         64.00     64.00    0.00
           S         16.00     16.00    0.00
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         81

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  24 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  18 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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%).

Structure description top

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

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

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]	D_x = 1.258 Mg m⁻³
M_r = 580.64	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3063 reflections
Hall symbol: -I 4ad	θ = 3.1–20.4°
a = 12.1767 (3) Å	µ = 0.24 mm⁻¹
c = 41.055 (3) Å	T = 193 K
V = 6087.2 (4) Å³	Block, colourless
Z = 8	0.22 × 0.18 × 0.11 mm
F(000) = 2432

Data collection top

Bruker SMART CCD diffractometer	2699 independent reflections
Radiation source: fine-focus sealed tube	1517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.108
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.950, T_max = 0.975	k = −10→13
20660 measured reflections	l = −48→48

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.102P)²] where P = (F_o² + 2F_c²)/3
2699 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.38 e Å⁻³
81 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Na(C₂₅H₃₃N₂O₆S₂)(H₂O)₂]	Z = 8
M_r = 580.64	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.24 mm⁻¹
a = 12.1767 (3) Å	T = 193 K
c = 41.055 (3) Å	0.22 × 0.18 × 0.11 mm
V = 6087.2 (4) Å³

Data collection top

Bruker SMART CCD diffractometer	2699 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1517 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.975	R_int = 0.108
20660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	81 restraints
wR(F²) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.38 e Å⁻³
2699 reflections	Δρ_min = −0.31 e Å⁻³
220 parameters

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	Occ. (<1)
C1	0.5271 (3)	0.0576 (3)	0.66152 (8)	0.0504 (9)
C2	0.4370 (3)	0.1229 (3)	0.65483 (9)	0.0515 (9)
H2	0.4037	0.1634	0.6720	0.062*
C3	0.3946 (3)	0.1304 (3)	0.62371 (9)	0.0502 (9)
C4	0.4459 (3)	0.0701 (3)	0.59912 (8)	0.0503 (9)
C5	0.5358 (3)	0.0018 (3)	0.60522 (8)	0.0534 (9)
C6	0.5743 (3)	−0.0025 (3)	0.63688 (8)	0.0555 (10)
H6	0.6353	−0.0483	0.6418	0.067*
C7	0.2966 (3)	0.2026 (3)	0.61710 (10)	0.0623 (10)
H7A	0.2892	0.2559	0.6352	0.075*
H7B	0.3103	0.2448	0.5969	0.075*
C8	0.1899 (4)	0.1414 (5)	0.61348 (17)	0.118 (2)
H8A	0.2000	0.0796	0.5985	0.178*
H8B	0.1337	0.1910	0.6048	0.178*
H8C	0.1664	0.1138	0.6348	0.178*
C9	0.5914 (3)	−0.0633 (3)	0.57863 (9)	0.0679 (11)
H9A	0.6275	−0.1282	0.5885	0.082*	0.50
H9B	0.5349	−0.0902	0.5632	0.082*	0.50
H9C	0.5855	−0.0251	0.5580	0.082*	0.50
H9D	0.6687	−0.0729	0.5837	0.082*	0.50
C10	0.6760 (6)	0.0018 (6)	0.55996 (17)	0.0545 (19)	0.50
H10A	0.7139	−0.0466	0.5445	0.082*	0.50
H10B	0.7295	0.0330	0.5752	0.082*	0.50
H10C	0.6396	0.0612	0.5480	0.082*	0.50
C10A	0.5352 (10)	−0.1738 (10)	0.5755 (3)	0.125 (4)	0.50
H10D	0.4582	−0.1629	0.5693	0.188*	0.50
H10E	0.5386	−0.2124	0.5965	0.188*	0.50
H10F	0.5723	−0.2176	0.5588	0.188*	0.50
C11	0.4461 (3)	0.1622 (3)	0.54605 (9)	0.0606 (10)
C12	0.4170 (4)	0.1490 (4)	0.51115 (9)	0.0894 (15)
H12A	0.4840	0.1366	0.4984	0.134*
H12B	0.3803	0.2156	0.5034	0.134*
H12C	0.3676	0.0860	0.5086	0.134*
C13	0.5000	0.2500	0.55988 (14)	0.0584 (14)
N1	0.4111 (3)	0.0809 (3)	0.56575 (8)	0.0583 (9)
O4	0.3487 (4)	0.2510 (8)	0.78203 (14)	0.262 (4)
Na1	0.5000	0.2500	0.74867 (6)	0.0922 (8)
S1	0.58590 (9)	0.05700 (8)	0.70120 (2)	0.0612 (4)
O1	0.4967 (4)	0.0733 (5)	0.72347 (10)	0.0889 (18)	0.869 (11)
O2	0.6390 (5)	−0.0470 (4)	0.70533 (9)	0.0819 (16)	0.869 (11)
O3	0.6590 (6)	0.1505 (5)	0.70159 (15)	0.119 (2)	0.869 (11)
O2A	0.6973 (18)	0.023 (4)	0.6994 (7)	0.099 (14)	0.131 (11)
O1A	0.506 (2)	0.001 (4)	0.7204 (9)	0.117 (15)	0.131 (11)
O3A	0.590 (3)	0.1683 (14)	0.7130 (8)	0.095 (9)	0.131 (11)
H1	0.377 (3)	0.022 (3)	0.5607 (9)	0.067 (13)*
H13	0.5000	0.2500	0.5828 (12)	0.048 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.045 (2)	0.045 (2)	0.061 (2)	−0.0081 (16)	−0.0005 (17)	0.0017 (17)
C2	0.050 (2)	0.047 (2)	0.057 (2)	−0.0037 (17)	0.0048 (18)	−0.0015 (17)
C3	0.045 (2)	0.041 (2)	0.065 (2)	−0.0067 (15)	−0.0019 (18)	0.0014 (17)
C4	0.052 (2)	0.044 (2)	0.055 (2)	−0.0092 (17)	−0.0070 (18)	−0.0011 (17)
C5	0.052 (2)	0.048 (2)	0.060 (2)	0.0011 (18)	−0.0046 (18)	−0.0016 (18)
C6	0.051 (2)	0.056 (2)	0.060 (2)	0.0065 (18)	−0.0029 (18)	−0.0007 (18)
C7	0.057 (2)	0.058 (2)	0.073 (2)	0.0061 (19)	−0.006 (2)	−0.002 (2)
C8	0.061 (3)	0.095 (4)	0.200 (6)	0.003 (3)	−0.011 (4)	0.006 (4)
C9	0.075 (3)	0.069 (3)	0.060 (2)	0.011 (2)	−0.010 (2)	−0.017 (2)
C10	0.042 (4)	0.072 (5)	0.049 (4)	0.016 (4)	0.002 (3)	−0.012 (4)
C10A	0.124 (10)	0.146 (11)	0.106 (8)	0.018 (8)	−0.003 (7)	−0.039 (8)
C11	0.067 (3)	0.058 (3)	0.057 (2)	0.002 (2)	−0.007 (2)	−0.003 (2)
C12	0.125 (4)	0.085 (3)	0.058 (3)	−0.008 (3)	−0.023 (3)	−0.003 (2)
C13	0.074 (4)	0.053 (4)	0.048 (3)	−0.003 (3)	0.000	0.000
N1	0.066 (2)	0.048 (2)	0.061 (2)	−0.0042 (17)	−0.0150 (16)	−0.0086 (17)
O4	0.124 (4)	0.491 (12)	0.171 (5)	−0.108 (6)	0.038 (3)	0.070 (6)
Na1	0.1482 (18)	0.099 (2)	0.0908 (17)	−0.0076 (14)	0.000	0.000
S1	0.0625 (7)	0.0653 (8)	0.0559 (6)	−0.0015 (5)	−0.0058 (5)	−0.0010 (5)
O1	0.087 (3)	0.120 (4)	0.059 (2)	0.034 (3)	0.005 (2)	−0.008 (3)
O2	0.087 (4)	0.096 (3)	0.063 (2)	0.038 (3)	−0.009 (2)	0.001 (2)
O3	0.125 (5)	0.136 (4)	0.096 (4)	−0.079 (4)	−0.045 (3)	0.026 (3)
O2A	0.040 (16)	0.18 (4)	0.078 (16)	0.064 (18)	−0.010 (13)	−0.05 (2)
O1A	0.045 (17)	0.17 (3)	0.14 (3)	−0.05 (2)	−0.006 (15)	0.09 (3)
O3A	0.14 (2)	0.065 (15)	0.081 (17)	−0.075 (15)	−0.050 (16)	0.017 (12)

Geometric parameters (Å, º) top

C1—C6	1.374 (5)	C10A—H10E	0.9800
C1—C2	1.382 (5)	C10A—H10F	0.9800
C1—S1	1.779 (4)	C11—N1	1.347 (5)
C2—C3	1.381 (5)	C11—C13	1.377 (4)
C2—H2	0.9500	C11—C12	1.484 (5)
C3—C4	1.396 (5)	C12—H12A	0.9800
C3—C7	1.507 (5)	C12—H12B	0.9800
C4—C5	1.397 (5)	C12—H12C	0.9800
C4—N1	1.440 (4)	C13—C11ⁱ	1.377 (4)
C5—C6	1.383 (5)	C13—H13	0.94 (4)
C5—C9	1.509 (5)	N1—H1	0.85 (4)
C6—H6	0.9500	O4—Na1	2.295 (5)
C7—C8	1.505 (6)	Na1—O3Aⁱ	2.08 (4)
C7—H7A	0.9900	Na1—O3A	2.08 (4)
C7—H7B	0.9900	Na1—O4ⁱ	2.295 (5)
C8—H8A	0.9800	Na1—O1	2.387 (6)
C8—H8B	0.9800	Na1—O1ⁱ	2.387 (6)
C8—H8C	0.9800	Na1—O3ⁱ	2.992 (9)
C9—C10	1.509 (8)	Na1—O3	2.992 (9)
C9—C10A	1.516 (13)	Na1—S1	3.2274 (19)
C9—H9A	0.9900	Na1—S1ⁱ	3.2274 (19)
C9—H9B	0.9900	S1—O2A	1.422 (13)
C9—H9C	0.9700	S1—O1A	1.430 (14)
C9—H9D	0.9700	S1—O2	1.431 (4)
C10—H10A	0.9800	S1—O1	1.433 (4)
C10—H10B	0.9800	S1—O3A	1.439 (15)
C10—H10C	0.9800	S1—O3	1.445 (4)
C10A—H10D	0.9800

C6—C1—C2	119.5 (3)	C11ⁱ—C13—H13	114.4 (3)
C6—C1—S1	120.2 (3)	C11—N1—C4	123.1 (3)
C2—C1—S1	120.2 (3)	C11—N1—H1	129 (3)
C3—C2—C1	121.2 (3)	C4—N1—H1	107 (3)
C3—C2—H2	119.4	O3Aⁱ—Na1—O3A	90.6 (16)
C1—C2—H2	119.4	O3Aⁱ—Na1—O4	89.7 (9)
C2—C3—C4	117.8 (3)	O3A—Na1—O4	147.7 (9)
C2—C3—C7	120.1 (3)	O3Aⁱ—Na1—O4ⁱ	147.7 (9)
C4—C3—C7	122.1 (3)	O3A—Na1—O4ⁱ	89.7 (9)
C3—C4—C5	122.3 (3)	O4—Na1—O4ⁱ	106.7 (3)
C3—C4—N1	120.5 (3)	O3Aⁱ—Na1—O1	96.7 (8)
C5—C4—N1	117.1 (3)	O3A—Na1—O1	43.4 (8)
C6—C5—C4	117.1 (3)	O4—Na1—O1	104.5 (3)
C6—C5—C9	120.5 (3)	O4ⁱ—Na1—O1	105.5 (3)
C4—C5—C9	122.3 (3)	O3Aⁱ—Na1—O1ⁱ	43.4 (8)
C1—C6—C5	122.0 (3)	O3A—Na1—O1ⁱ	96.7 (8)
C1—C6—H6	119.0	O4—Na1—O1ⁱ	105.5 (3)
C5—C6—H6	119.0	O4ⁱ—Na1—O1ⁱ	104.5 (3)
C8—C7—C3	114.4 (3)	O1—Na1—O1ⁱ	128.6 (3)
C8—C7—H7A	108.7	O3Aⁱ—Na1—O3ⁱ	8.7 (9)
C3—C7—H7A	108.7	O3A—Na1—O3ⁱ	94.6 (8)
C8—C7—H7B	108.7	O4—Na1—O3ⁱ	82.2 (2)
C3—C7—H7B	108.7	O4ⁱ—Na1—O3ⁱ	155.1 (3)
H7A—C7—H7B	107.6	O1—Na1—O3ⁱ	94.26 (17)
C7—C8—H8A	109.5	O1ⁱ—Na1—O3ⁱ	50.64 (15)
C7—C8—H8B	109.5	O3Aⁱ—Na1—O3	94.6 (8)
H8A—C8—H8B	109.5	O3A—Na1—O3	8.7 (9)
C7—C8—H8C	109.5	O4—Na1—O3	155.1 (3)
H8A—C8—H8C	109.5	O4ⁱ—Na1—O3	82.2 (2)
H8B—C8—H8C	109.5	O1—Na1—O3	50.64 (15)
C10—C9—C5	113.4 (4)	O1ⁱ—Na1—O3	94.26 (17)
C10—C9—C10A	137.1 (6)	O3ⁱ—Na1—O3	99.5 (2)
C5—C9—C10A	108.9 (5)	O3Aⁱ—Na1—S1	95.4 (8)
C10—C9—H9A	108.9	O3A—Na1—S1	19.4 (8)
C5—C9—H9A	108.9	O4—Na1—S1	128.6 (2)
C10A—C9—H9A	61.7	O4ⁱ—Na1—S1	95.5 (2)
C10—C9—H9B	108.9	O1—Na1—S1	24.15 (13)
C5—C9—H9B	108.9	O1ⁱ—Na1—S1	112.89 (15)
C10A—C9—H9B	48.6	O3ⁱ—Na1—S1	96.57 (13)
H9A—C9—H9B	107.7	O3—Na1—S1	26.52 (8)
C10—C9—H9C	49.8	O3Aⁱ—Na1—S1ⁱ	19.4 (8)
C5—C9—H9C	110.3	O3A—Na1—S1ⁱ	95.4 (8)
C10A—C9—H9C	108.6	O4—Na1—S1ⁱ	95.5 (2)
H9A—C9—H9C	140.5	O4ⁱ—Na1—S1ⁱ	128.6 (2)
H9B—C9—H9C	63.2	O1—Na1—S1ⁱ	112.89 (15)
C10—C9—H9D	60.7	O1ⁱ—Na1—S1ⁱ	24.15 (13)
C5—C9—H9D	110.1	O3ⁱ—Na1—S1ⁱ	26.52 (8)
C10A—C9—H9D	110.4	O3—Na1—S1ⁱ	96.57 (13)
H9A—C9—H9D	52.2	S1—Na1—S1ⁱ	105.70 (8)
H9B—C9—H9D	140.4	O2A—S1—O1A	123 (2)
H9C—C9—H9D	108.5	O2A—S1—O2	47 (2)
C9—C10—H9C	40.0	O1A—S1—O2	80 (2)
C9—C10—H9D	39.3	O2A—S1—O1	142.8 (14)
H9C—C10—H9D	78.1	O1A—S1—O1	36 (2)
C9—C10—H10A	109.5	O2—S1—O1	112.9 (3)
H9C—C10—H10A	103.5	O2A—S1—O3A	105.1 (19)
H9D—C10—H10A	95.4	O1A—S1—O3A	107 (2)
C9—C10—H10B	109.5	O2—S1—O3A	141.0 (13)
H9C—C10—H10B	142.3	O1—S1—O3A	71.5 (17)
H9D—C10—H10B	81.0	O2A—S1—O3	69 (2)
C9—C10—H10C	109.5	O1A—S1—O3	142 (2)
H9C—C10—H10C	75.1	O2—S1—O3	114.7 (3)
H9D—C10—H10C	146.8	O1—S1—O3	110.5 (4)
C9—C10A—H10D	109.5	O3A—S1—O3	39.9 (15)
C9—C10A—H10E	109.5	O2A—S1—C1	109.8 (11)
H10D—C10A—H10E	109.5	O1A—S1—C1	103.4 (15)
C9—C10A—H10F	109.5	O2—S1—C1	107.1 (2)
H10D—C10A—H10F	109.5	O1—S1—C1	106.2 (2)
H10E—C10A—H10F	109.5	O3A—S1—C1	108.5 (12)
N1—C11—C13	118.2 (4)	O3—S1—C1	104.8 (2)
N1—C11—C12	115.1 (4)	O2A—S1—Na1	123.7 (14)
C13—C11—C12	126.6 (4)	O1A—S1—Na1	78 (3)
C11—C12—H12A	109.5	O2—S1—Na1	135.95 (16)
C11—C12—H12B	109.5	O1—S1—Na1	43.0 (3)
H12A—C12—H12B	109.5	O3A—S1—Na1	28.8 (17)
C11—C12—H12C	109.5	O3—S1—Na1	67.6 (4)
H12A—C12—H12C	109.5	C1—S1—Na1	114.80 (13)
H12B—C12—H12C	109.5	S1—O1—Na1	112.9 (4)
C11—C13—C11ⁱ	131.3 (5)	S1—O3—Na1	85.9 (4)
C11—C13—H13	114.4 (3)	S1—O3A—Na1	132 (2)

C6—C1—C2—C3	−1.1 (5)	O4ⁱ—Na1—S1—O1	116.1 (4)
S1—C1—C2—C3	175.5 (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—O1	176.1 (4)
C2—C3—C4—C5	1.4 (5)	S1ⁱ—Na1—S1—O1	−111.1 (3)
C7—C3—C4—C5	−179.0 (3)	O3Aⁱ—Na1—S1—O3A	76 (3)
C2—C3—C4—N1	−175.1 (3)	O4—Na1—S1—O3A	170 (3)
C7—C3—C4—N1	4.4 (5)	O4ⁱ—Na1—S1—O3A	−73 (3)
C3—C4—C5—C6	−1.2 (5)	O1—Na1—S1—O3A	171 (3)
N1—C4—C5—C6	175.4 (3)	O1ⁱ—Na1—S1—O3A	35 (3)
C3—C4—C5—C9	−179.9 (3)	O3ⁱ—Na1—S1—O3A	85 (3)
N1—C4—C5—C9	−3.2 (5)	O3—Na1—S1—O3A	−13 (3)
C2—C1—C6—C5	1.2 (5)	S1ⁱ—Na1—S1—O3A	60 (3)
S1—C1—C6—C5	−175.4 (3)	O3Aⁱ—Na1—S1—O3	89.5 (9)
C4—C5—C6—C1	−0.1 (5)	O3A—Na1—S1—O3	13 (3)
C9—C5—C6—C1	178.6 (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—C8	77.7 (5)	O1—Na1—S1—O3	−176.1 (4)
C6—C5—C9—C10	−94.6 (5)	O1ⁱ—Na1—S1—O3	48.3 (3)
C4—C5—C9—C10	84.0 (5)	O3ⁱ—Na1—S1—O3	98.1 (3)
C6—C5—C9—C10A	92.4 (6)	S1ⁱ—Na1—S1—O3	72.7 (2)
C4—C5—C9—C10A	−89.0 (6)	O3Aⁱ—Na1—S1—C1	−7.0 (9)
N1—C11—C13—C11ⁱ	172.5 (4)	O3A—Na1—S1—C1	−83 (3)
C12—C11—C13—C11ⁱ	−10.5 (3)	O4—Na1—S1—C1	86.9 (3)
C13—C11—N1—C4	−12.9 (5)	O4ⁱ—Na1—S1—C1	−156.5 (2)
C12—C11—N1—C4	169.8 (4)	O1—Na1—S1—C1	87.4 (3)
C3—C4—N1—C11	83.0 (5)	O1ⁱ—Na1—S1—C1	−48.26 (18)
C5—C4—N1—C11	−93.7 (4)	O3ⁱ—Na1—S1—C1	1.62 (15)
C6—C1—S1—O2A	20 (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—Na1	86 (3)
C2—C1—S1—O1A	71 (2)	O1A—S1—O1—Na1	160 (3)
C6—C1—S1—O2	−29.4 (4)	O2—S1—O1—Na1	133.7 (3)
C2—C1—S1—O2	154.1 (4)	O3A—S1—O1—Na1	−4.7 (13)
C6—C1—S1—O1	−150.2 (4)	O3—S1—O1—Na1	3.8 (4)
C2—C1—S1—O1	33.2 (4)	C1—S1—O1—Na1	−109.2 (2)
C6—C1—S1—O3A	134.3 (19)	O3Aⁱ—Na1—O1—S1	88.2 (10)
C2—C1—S1—O3A	−42.2 (19)	O3A—Na1—O1—S1	4.4 (12)
C6—C1—S1—O3	92.8 (5)	O4—Na1—O1—S1	179.6 (3)
C2—C1—S1—O3	−83.7 (5)	O4ⁱ—Na1—O1—S1	−68.1 (3)
C6—C1—S1—Na1	164.6 (3)	O1ⁱ—Na1—O1—S1	55.6 (2)
C2—C1—S1—Na1	−11.9 (3)	O3ⁱ—Na1—O1—S1	96.6 (3)
O3Aⁱ—Na1—S1—O2A	132 (3)	O3—Na1—O1—S1	−2.2 (2)
O3A—Na1—S1—O2A	56 (3)	S1ⁱ—Na1—O1—S1	77.1 (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—O2A	91 (3)	O1—S1—O3—Na1	−2.8 (3)
O3ⁱ—Na1—S1—O2A	141 (3)	O3A—S1—O3—Na1	9.8 (19)
O3—Na1—S1—O2A	43 (3)	C1—S1—O3—Na1	111.13 (16)
S1ⁱ—Na1—S1—O2A	115 (3)	O3Aⁱ—Na1—O3—S1	−92.9 (9)
O3Aⁱ—Na1—S1—O1A	−106.4 (16)	O3A—Na1—O3—S1	−30 (5)
O3A—Na1—S1—O1A	177 (3)	O4—Na1—O3—S1	6.3 (6)
O4—Na1—S1—O1A	−12.5 (14)	O4ⁱ—Na1—O3—S1	119.5 (3)
O4ⁱ—Na1—S1—O1A	104.1 (14)	O1—Na1—O3—S1	2.0 (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—O1A	164.1 (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—O2	116 (3)	O1—S1—O3A—Na1	6.6 (19)
O4—Na1—S1—O2	−73.7 (5)	O3—S1—O3A—Na1	−161 (4)
O4ⁱ—Na1—S1—O2	42.9 (4)	C1—S1—O3A—Na1	108 (2)
O1—Na1—S1—O2	−73.2 (4)	O3Aⁱ—Na1—O3A—S1	−105 (3)
O1ⁱ—Na1—S1—O2	151.2 (4)	O4—Na1—O3A—S1	−14 (4)
O3ⁱ—Na1—S1—O2	−159.0 (4)	O4ⁱ—Na1—O3A—S1	108 (2)
O3—Na1—S1—O2	102.9 (4)	O1—Na1—O3A—S1	−5.5 (16)
S1ⁱ—Na1—S1—O2	175.6 (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—S1	138 (7)
O4—Na1—S1—O1	−0.5 (4)	S1ⁱ—Na1—O3A—S1	−123 (2)

Symmetry code: (i) −x+1, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱ	0.85 (4)	2.01 (4)	2.854 (6)	175 (4)
N1—H1···O2Aⁱⁱ	0.85 (4)	2.08 (5)	2.83 (3)	148 (4)

Symmetry code: (ii) −y+1/4, x−3/4, −z+5/4.

Experimental details

Crystal data
Chemical formula	[Na(C₂₅H₃₃N₂O₆S₂)(H₂O)₂]
M_r	580.64
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	193
a, c (Å)	12.1767 (3), 41.055 (3)
V (Å³)	6087.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.18 × 0.11

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	20660, 2699, 1517
R_int	0.108
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.186, 1.01
No. of reflections	2699
No. of parameters	220
No. of restraints	81
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2001), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.85 (4)	2.01 (4)	2.854 (6)	175 (4)
N1—H1···O2Aⁱ	0.85 (4)	2.08 (5)	2.83 (3)	148 (4)

Symmetry code: (i) −y+1/4, x−3/4, −z+5/4.

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