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Acta Cryst. (2007). E63, m2910    [ doi:10.1107/S1600536807053950 ]

Di-[mu]-aqua-bis[(2-amino-4,5-dimethylbenzenesulfonato-[kappa]N)aquasilver(I)]

X.-W. Dong, W. Li and Y.-J. Li

Abstract top

In the title compound, [Ag2(C8H10NO3S)2(H2O)4], each AgI atom is coordinated by three water molecules and one N atom from a 2-amino-4,5-dimethylbenzenesulfonate ligand in a severely distorted tetrahedral geometry. The two AgI atoms are bridged by two water molecules, forming a centrosymmetric binuclear complex. The distance of 3.615 (9) Å between the two AgI atoms suggests that there are no Ag...Ag interaction within the binuclear molecule.

Comment top

The title compound shows a binuclear structure (Fig. 1). Each AgI atom is coordinated by three water molecules with Ag—Obridge distance larger than that of Ag—Oterminal (Table 1), but both in the range of normal Ag—O distance. The AgI atom has a seriously distorted tetrahedral coodination geometry. The two AgI atoms are bridged by two water molecules, forming a binuclear structure. The Ag···Ag distance is 3.615 (9) Å, indicating no metal–metal interaction within the binuclear molecule. The molecular geometry of the title compound has been changed largely when compared with a related compound (Li et al., 2007). Adjacent molecules are connected by O—H···O and N—H···O hydrogen bonds (Table2), forming a two-dimensional supramolecular structure (Fig.2).

Related literature top

The related compound, [Ag(C8H10NO3S)(H2O)2], has a mononuclear structure (Li et al., 2007).

Experimental top

An aqueous solution (10 ml) of 2-amino-4,5-dimethylbenzenesulfonic acid (0.101 g, 0.5 mmol) was added to solid Ag2CO3 (0.069 g, 0.25 mmol) with stirring for several minutes until no further CO2 was given off. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M). Then a solution of β-picoline (0.039 g, 0.5 mmol) in CH3OH (8 ml) was added with stirring for 30 min. Crystals of the title compound were obtained by evaporation of the solution for several days at room temperature. β-Picoline did not react with the silversulfonate.

Refinement top

H atoms bonded to C atoms were positioned geometrically and refined as riding, with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic, and C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl groups. H atoms bonded to N atom and water molecules were located in a difference map and refined isotropically.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) −x, 1 − y, 1 − z.]
[Figure 2] Fig. 2. Two-dimensional supramolecular structure of the title compound, formed through hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted.
Di-µ-aqua-bis[(2-amino-4,5-dimethylbenzenesulfonato-κN)aquasilver(I)] top
Crystal data top
[Ag2(C8H10NO3S)2(H2O)4]F000 = 688
Mr = 688.26Dx = 1.909 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2822 reflections
a = 12.5391 (11) Åθ = 1.7–28.3º
b = 8.7406 (7) ŵ = 1.86 mm−1
c = 11.3861 (10) ÅT = 292 (2) K
β = 106.319 (1)ºPlate, colorless
V = 1197.63 (18) Å30.35 × 0.25 × 0.18 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer		2822 independent reflections
Radiation source: fine-focus sealed tube2077 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
T = 292(2) Kθmax = 28.3º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)		h = −14→16
Tmin = 0.515, Tmax = 0.715k = −10→11
7202 measured reflectionsl = −13→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.074  w = 1/[σ2(Fo2) + (0.0359P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
2822 reflectionsΔρmax = 0.73 e Å−3
170 parametersΔρmin = −0.55 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ag2(C8H10NO3S)2(H2O)4]V = 1197.63 (18) Å3
Mr = 688.26Z = 2
Monoclinic, P21/cMo Kα
a = 12.5391 (11) ŵ = 1.86 mm−1
b = 8.7406 (7) ÅT = 292 (2) K
c = 11.3861 (10) Å0.35 × 0.25 × 0.18 mm
β = 106.319 (1)º
Data collection top
Bruker SMART APEX CCD
diffractometer		2822 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)		2077 reflections with I > 2σ(I)
Tmin = 0.515, Tmax = 0.715Rint = 0.063
7202 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0316 restraints
wR(F2) = 0.074H atoms treated by a mixture of
independent and constrained refinement
S = 0.92Δρmax = 0.73 e Å−3
2822 reflectionsΔρmin = −0.55 e Å−3
170 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.09929 (2)0.40908 (3)0.62723 (2)0.05391 (11)
C10.27697 (19)0.0783 (3)0.6403 (2)0.0286 (5)
C20.3878 (2)0.0391 (3)0.6914 (2)0.0336 (6)
H20.4056−0.03150.75510.040*
C30.4731 (2)0.1015 (3)0.6508 (3)0.0358 (6)
C40.4451 (2)0.2062 (3)0.5542 (2)0.0345 (6)
C50.3339 (2)0.2459 (3)0.5042 (2)0.0341 (6)
H50.31580.31660.44060.041*
C60.24956 (19)0.1846 (3)0.5454 (2)0.0285 (5)
C70.5317 (2)0.2733 (4)0.5006 (3)0.0453 (7)
H7A0.49730.34510.43750.068*
H7B0.56590.19300.46650.068*
H7C0.58720.32470.56370.068*
C80.5921 (2)0.0541 (4)0.7108 (3)0.0501 (8)
H8A0.62430.01480.64970.075*
H8B0.5935−0.02360.77070.075*
H8C0.63390.14120.74980.075*
N10.13838 (19)0.2376 (3)0.4950 (2)0.0345 (5)
O10.12030 (16)0.1204 (2)0.74406 (18)0.0406 (4)
O20.09741 (15)−0.0815 (2)0.59466 (19)0.0458 (5)
O30.22979 (15)−0.1105 (2)0.79442 (19)0.0477 (5)
O1W−0.1147 (2)0.3633 (3)0.5210 (2)0.0572 (6)
O2W0.1232 (2)0.5614 (3)0.7848 (2)0.0672 (7)
S10.17342 (5)−0.00523 (7)0.69825 (6)0.02996 (15)
H1N0.088 (3)0.177 (4)0.486 (3)0.076 (13)*
H1A−0.125 (2)0.278 (3)0.486 (3)0.047 (9)*
H1B−0.152 (3)0.364 (4)0.564 (3)0.063 (12)*
H2N0.128 (2)0.287 (3)0.419 (3)0.038 (7)*
H2B0.159 (3)0.648 (4)0.770 (3)0.057 (10)*
H2A0.052 (3)0.559 (6)0.805 (4)0.120 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.06478 (19)0.04141 (16)0.06053 (19)0.00582 (11)0.02579 (14)−0.00630 (11)
C10.0268 (13)0.0302 (13)0.0298 (13)−0.0002 (10)0.0095 (10)−0.0024 (10)
C20.0321 (14)0.0371 (14)0.0321 (14)0.0013 (11)0.0096 (11)0.0015 (11)
C30.0269 (13)0.0420 (15)0.0390 (15)−0.0012 (11)0.0100 (11)−0.0081 (12)
C40.0339 (13)0.0384 (14)0.0337 (14)−0.0094 (11)0.0138 (11)−0.0067 (12)
C50.0385 (14)0.0358 (14)0.0287 (13)−0.0044 (11)0.0103 (11)0.0009 (11)
C60.0290 (12)0.0296 (13)0.0271 (12)−0.0013 (10)0.0078 (10)−0.0047 (10)
C70.0377 (15)0.0569 (19)0.0459 (17)−0.0137 (13)0.0190 (13)−0.0043 (14)
C80.0289 (14)0.063 (2)0.058 (2)0.0013 (14)0.0118 (14)0.0009 (16)
N10.0323 (12)0.0355 (13)0.0355 (13)0.0021 (10)0.0091 (10)0.0045 (10)
O10.0416 (11)0.0412 (11)0.0460 (11)0.0032 (8)0.0237 (9)−0.0013 (9)
O20.0371 (11)0.0474 (13)0.0513 (12)−0.0114 (8)0.0097 (9)−0.0092 (9)
O30.0358 (11)0.0527 (13)0.0562 (13)0.0038 (8)0.0153 (10)0.0243 (10)
O1W0.0778 (17)0.0461 (14)0.0578 (15)−0.0058 (12)0.0354 (14)−0.0052 (12)
O2W0.0702 (17)0.0601 (15)0.0814 (19)−0.0123 (13)0.0378 (14)−0.0108 (13)
S10.0259 (3)0.0309 (3)0.0338 (3)−0.0009 (2)0.0096 (3)0.0024 (3)
Geometric parameters (Å, °) top
Ag1—O2W2.186 (3)C7—H7A0.9600
Ag1—N12.273 (2)C7—H7B0.9600
Ag1—O1W2.645 (3)C7—H7C0.9600
Ag1—O1Wi2.651 (4)C8—H8A0.9600
C1—C21.391 (3)C8—H8B0.9600
C1—C61.394 (3)C8—H8C0.9600
C1—S11.771 (2)N1—H1N0.81 (3)
C2—C31.390 (4)N1—H2N0.95 (3)
C2—H20.9300O1—S11.4551 (19)
C3—C41.398 (4)O2—S11.453 (2)
C3—C81.513 (4)O3—S11.4524 (19)
C4—C51.394 (4)O1W—H1A0.84 (3)
C4—C71.506 (3)O1W—H1B0.76 (3)
C5—C61.380 (3)O2W—H2B0.92 (3)
C5—H50.9300O2W—H2A0.98 (4)
C6—N11.427 (3)
O2W—Ag1—N1160.00 (9)H7A—C7—H7B109.5
O1W—Ag1—O1Wi93.92 (8)C4—C7—H7C109.5
O1W—Ag1—O2W110.79 (9)H7A—C7—H7C109.5
O1W—Ag1—N188.69 (8)H7B—C7—H7C109.5
O2W—Ag1—O1Wi92.74 (8)C3—C8—H8A109.5
N1—Ag1—O1Wi90.30 (8)C3—C8—H8B109.5
C2—C1—C6119.3 (2)H8A—C8—H8B109.5
C2—C1—S1119.59 (19)C3—C8—H8C109.5
C6—C1—S1121.14 (18)H8A—C8—H8C109.5
C3—C2—C1122.4 (2)H8B—C8—H8C109.5
C3—C2—H2118.8C6—N1—Ag1108.40 (16)
C1—C2—H2118.8C6—N1—H1N118 (3)
C2—C3—C4118.1 (2)Ag1—N1—H1N102 (3)
C2—C3—C8119.7 (3)C6—N1—H2N112.8 (15)
C4—C3—C8122.1 (2)Ag1—N1—H2N107.7 (16)
C5—C4—C3119.1 (2)H1N—N1—H2N106 (3)
C5—C4—C7119.4 (2)H1A—O1W—H1B106 (3)
C3—C4—C7121.5 (2)Ag1—O2W—H2B108 (2)
C6—C5—C4122.6 (2)Ag1—O2W—H2A105 (3)
C6—C5—H5118.7H2B—O2W—H2A125 (4)
C4—C5—H5118.7O3—S1—O2112.99 (12)
C5—C6—C1118.5 (2)O3—S1—O1112.48 (12)
C5—C6—N1119.5 (2)O2—S1—O1112.04 (12)
C1—C6—N1121.9 (2)O3—S1—C1106.83 (11)
C4—C7—H7A109.5O2—S1—C1105.61 (12)
C4—C7—H7B109.5O1—S1—C1106.26 (11)
C6—C1—C2—C3−0.4 (4)S1—C1—C6—C5179.91 (18)
S1—C1—C2—C3−179.4 (2)C2—C1—C6—N1−175.5 (2)
C1—C2—C3—C4−0.7 (4)S1—C1—C6—N13.5 (3)
C1—C2—C3—C8179.8 (2)C5—C6—N1—Ag1−99.9 (2)
C2—C3—C4—C51.2 (4)C1—C6—N1—Ag176.5 (2)
C8—C3—C4—C5−179.3 (2)O2W—Ag1—N1—C67.0 (4)
C2—C3—C4—C7−177.0 (2)C2—C1—S1—O3−1.5 (2)
C8—C3—C4—C72.5 (4)C6—C1—S1—O3179.50 (19)
C3—C4—C5—C6−0.8 (4)C2—C1—S1—O2−122.0 (2)
C7—C4—C5—C6177.5 (2)C6—C1—S1—O259.0 (2)
C4—C5—C6—C1−0.3 (4)C2—C1—S1—O1118.8 (2)
C4—C5—C6—N1176.2 (2)C6—C1—S1—O1−60.2 (2)
C2—C1—C6—C50.9 (4)
Symmetry codes: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O2ii0.84 (3)2.02 (3)2.830 (3)161 (3)
O1W—H1B···O3iii0.76 (3)2.12 (3)2.874 (3)169 (4)
O2W—H2A···O1iii0.98 (4)2.14 (4)3.022 (3)148 (4)
O2W—H2B···O3iv0.92 (3)2.28 (3)3.154 (3)159 (3)
N1—H1N···O2ii0.81 (3)2.40 (3)3.154 (3)156 (4)
N1—H2N···O1v0.95 (3)2.12 (3)3.065 (3)172 (2)
Symmetry codes: (ii) −x, −y, −z+1; (iii) −x, y+1/2, −z+3/2; (iv) x, y+1, z; (v) x, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Ag1—O2W2.186 (3)Ag1—O1W2.645 (3)
Ag1—N12.273 (2)Ag1—O1Wi2.651 (4)
O2W—Ag1—N1160.00 (9)O1W—Ag1—N188.69 (8)
O1W—Ag1—O1Wi93.92 (8)O2W—Ag1—O1Wi92.74 (8)
O1W—Ag1—O2W110.79 (9)N1—Ag1—O1Wi90.30 (8)
Symmetry codes: (i) −x, −y+1, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O2ii0.84 (3)2.02 (3)2.830 (3)161 (3)
O1W—H1B···O3iii0.76 (3)2.12 (3)2.874 (3)169 (4)
O2W—H2A···O1iii0.98 (4)2.14 (4)3.022 (3)148 (4)
O2W—H2B···O3iv0.92 (3)2.28 (3)3.154 (3)159 (3)
N1—H1N···O2ii0.81 (3)2.40 (3)3.154 (3)156 (4)
N1—H2N···O1v0.95 (3)2.12 (3)3.065 (3)172 (2)
Symmetry codes: (ii) −x, −y, −z+1; (iii) −x, y+1/2, −z+3/2; (iv) x, y+1, z; (v) x, −y+1/2, z−1/2.
Acknowledgements top

We thank the Jilin Agriculture Science and Technology College, China, for support.

references
References top

Bruker (1997). SMART. Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA.

Li, Y.-J., Li, S.-H. & Dong, X.-W. (2007). Acta Cryst. E63, m2695–?.

Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.