Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038305/lh2437sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038305/lh2437Isup2.hkl |
CCDC reference: 660086
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%).
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.
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 crystal structures of β-diimine Schiff base compounds have been reported (Brownstein et al., 1983; Lesikar & Richards, 2006).
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.
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. |
[Na(C25H33N2O6S2)(H2O)2] | Dx = 1.258 Mg m−3 |
Mr = 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 |
Bruker SMART CCD diffractometer | 2699 independent reflections |
Radiation source: fine-focus sealed tube | 1517 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.950, Tmax = 0.975 | k = −10→13 |
20660 measured reflections | l = −48→48 |
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(Fo2) + (0.102P)2] where P = (Fo2 + 2Fc2)/3 |
2699 reflections | (Δ/σ)max < 0.001 |
220 parameters | Δρmax = 0.38 e Å−3 |
81 restraints | Δρmin = −0.31 e Å−3 |
[Na(C25H33N2O6S2)(H2O)2] | Z = 8 |
Mr = 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 |
Bruker SMART CCD diffractometer | 2699 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1517 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.975 | Rint = 0.108 |
20660 measured reflections |
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 | Δρmax = 0.38 e Å−3 |
2699 reflections | Δρmin = −0.31 e Å−3 |
220 parameters |
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. |
x | y | z | Uiso*/Ueq | 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)* |
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) |
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. |
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] |
Mr | 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) |
Tmin, Tmax | 0.950, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20660, 2699, 1517 |
Rint | 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 |
Δρmax, Δρmin (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.
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. |
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.