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Acta Cryst. (2007). E63, m2230    [ doi:10.1107/S1600536807036495 ]

Diaquasilver(I) 6-aminonaphthalene-1-sulfonate monohydrate

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

Abstract top

The title compound, [Ag(H2O)2](C10H8NO3S)·H2O, has a mononuclear structure in which the Ag+ cation is coordinated by two O atoms from two water molecules. The 6-aminonaphthalene-1-sulfonate anion does not coordinate to the Ag+ ion, but acts as a counter-ion. Intermolecular O-H...O and N-H...O hydrogen bonds link the ions and water molecules.

Comment top

The structure of the title compound, (I) (Fig. 1), containing three water molecules and a 6-amino-1-naphthalenesulfonate (L) anion, is described. In (I), two water molecules are coordinated to the metal, resulting in a slightly distorted linear coordination geometry for Ag (Table 1). Atoms Ag1, O1W, O2W are almost collinear; the angle O1W—Ag1—O2W is 176.0 (6)°. The Ag1—O1W and Ag1—O2W distances are 2.132 (7)Å and 2.139 (7) Å; the Ag—Owater distance is similar to the corresponding value in a related compound (Shangguan et al., 2007). The 6-amino-1-naphthalenesulfonate anion does not coordinate to the Ag+ ion, but acts as a counterion.

In (I), the coordination ability of the oxygen atoms of the water molecules is evidently stronger than that of the sulfonate group and the latter group does not coordinate to the Ag+ ion. Adjacent ions and water molecules are interconnected by strong O—H···O and N—H···O hydrogen-bonding interactions (Table 2). Thus, the compound forms a three-dimensional supramolecular framework through extensive intermolecular hydrogen bonding (Fig. 2).

Related literature top

The related compound, [Ag(C5H5N)(H2O)](C6H4Cl2NO3S)·2H2O, has a mononuclear structure in which the Ag+ cation is coordinated by one N atom from a pyridine molecule and one O atom from a water molecule, and the 2,5-dichloro-4-aminobenzenesulfonate anion is not coordinated to Ag (Shangguan et al., 2007).

Experimental top

An aqueous solution (10 ml) of 6-amino-1-naphthalenesulfonic acid (0.112 g, 0.5 mmol) was added to solid Ag2CO3 (0.069 g, 0.25 mmol) and stirred 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). Crystals of (I) were obtained by evaporation of the solution over several days at room temperature.

Refinement top

All H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and Uiso(H)= 1.2Ueq(C). The water H atoms were located in a difference Fourier map and refined isotropically [O—H = 0.83 (4)–0.93 (4) Å and Uiso(H) = 0.06 Å2. The amino H atoms were located in a difference Fourier map and refined isotropically with the N—H distance restrained to 0.9 (5) Å and Uiso(H) = 0.06 Å2.

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. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Three-dimensional supramolecular framework of (I), formed through hydrogen-bonding (dashed lines) interactions. H atoms not involved in hydrogen bonding have been omitted.
Diaquasilver(I) 6-aminonaphthalene-1-sulfonate monohydrate top
Crystal data top
[Ag(H2O)2](C10H8NO3S)·H2OF(000) = 384
Mr = 384.15Dx = 1.872 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2177 reflections
a = 8.8780 (11) Åθ = 2.4–28.3°
b = 9.0141 (11) ŵ = 1.65 mm−1
c = 9.5576 (12) ÅT = 292 K
β = 116.989 (2)°Block, white
V = 681.57 (15) Å30.25 × 0.23 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer		2177 independent reflections
Radiation source: fine-focus sealed tube1740 reflections with I > 2σ(I)
graphiteRint = 0.052
φ and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.652, Tmax = 0.718k = −11→6
4251 measured reflectionsl = −12→12
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)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0984P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2177 reflectionsΔρmax = 0.49 e Å−3
196 parametersΔρmin = −0.44 e Å−3
14 restraintsAbsolute structure: Flack (1983), with 482 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.08 (6)
Crystal data top
[Ag(H2O)2](C10H8NO3S)·H2OV = 681.57 (15) Å3
Mr = 384.15Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.8780 (11) ŵ = 1.65 mm−1
b = 9.0141 (11) ÅT = 292 K
c = 9.5576 (12) Å0.25 × 0.23 × 0.20 mm
β = 116.989 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2177 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1740 reflections with I > 2σ(I)
Tmin = 0.652, Tmax = 0.718Rint = 0.052
4251 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141Δρmax = 0.49 e Å−3
S = 1.01Δρmin = −0.44 e Å−3
2177 reflectionsAbsolute structure: Flack (1983), with 482 Friedel pairs
196 parametersFlack parameter: −0.08 (6)
14 restraints
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
xyzUiso*/Ueq
Ag10.80067 (8)0.46498 (10)0.74795 (7)0.0652 (3)
C10.5086 (7)0.3207 (8)0.3324 (7)0.0294 (12)
C20.3669 (7)0.4157 (7)0.2499 (7)0.0281 (12)
C30.3425 (7)0.5079 (7)0.1217 (7)0.0313 (14)
H30.42270.50650.08440.038*
C40.2089 (7)0.5968 (8)0.0524 (7)0.0327 (13)
H40.20030.6571−0.02990.039*
C50.0779 (8)0.6023 (8)0.1009 (8)0.0358 (14)
C60.0952 (8)0.5125 (8)0.2234 (7)0.0366 (14)
H60.01270.51500.25790.044*
C70.2355 (8)0.4159 (8)0.2989 (7)0.0325 (13)
C80.2550 (8)0.3263 (9)0.4263 (8)0.0395 (15)
H80.17290.32890.46130.047*
C90.3937 (10)0.2342 (9)0.5009 (9)0.0461 (18)
H90.40220.17190.58170.055*
C100.5212 (11)0.2362 (9)0.4525 (9)0.0454 (17)
H100.61670.17740.50510.055*
N1−0.0621 (9)0.6922 (10)0.0216 (10)0.063 (2)
O10.7407 (6)0.4647 (11)0.2927 (7)0.0617 (14)
O20.5950 (8)0.2620 (10)0.1133 (7)0.075 (2)
O1W0.6141 (10)0.4549 (14)0.8300 (9)0.0801 (18)
O30.8013 (7)0.2118 (8)0.3828 (8)0.0615 (16)
O2W0.9824 (9)0.4600 (17)0.6590 (8)0.086 (2)
O3W0.7058 (8)0.7430 (8)0.1647 (9)0.0691 (18)
S10.6754 (2)0.3129 (2)0.2756 (2)0.0403 (4)
H1A−0.137 (9)0.713 (10)0.053 (10)0.060*
H1W0.543 (9)0.530 (8)0.825 (9)0.060*
H2A−0.050 (11)0.783 (7)−0.014 (12)0.060*
H2W0.632 (12)0.426 (9)0.922 (7)0.060*
H3W0.935 (9)0.428 (10)0.568 (6)0.060*
H4W1.082 (7)0.423 (10)0.718 (8)0.060*
H5W0.696 (11)0.649 (6)0.176 (10)0.060*
H6W0.616 (8)0.770 (9)0.069 (7)0.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0660 (4)0.0669 (4)0.0606 (4)−0.0042 (4)0.0267 (3)0.0046 (4)
C10.025 (3)0.028 (3)0.031 (3)0.006 (3)0.010 (2)−0.004 (3)
C20.025 (3)0.025 (3)0.033 (3)−0.006 (2)0.012 (2)−0.006 (2)
C30.028 (3)0.036 (4)0.031 (3)−0.006 (2)0.014 (2)−0.004 (2)
C40.032 (3)0.035 (3)0.031 (3)−0.004 (3)0.014 (2)0.000 (3)
C50.034 (3)0.034 (3)0.038 (3)0.005 (3)0.016 (3)−0.005 (3)
C60.029 (3)0.039 (4)0.047 (3)−0.008 (2)0.021 (3)−0.005 (3)
C70.032 (3)0.034 (3)0.032 (3)−0.004 (2)0.015 (2)−0.005 (2)
C80.039 (3)0.042 (4)0.043 (3)−0.002 (3)0.024 (3)−0.002 (3)
C90.053 (4)0.039 (4)0.043 (4)0.001 (3)0.020 (4)0.016 (3)
C100.050 (4)0.041 (4)0.040 (4)−0.004 (3)0.015 (3)0.004 (3)
N10.046 (4)0.069 (5)0.074 (5)0.020 (4)0.028 (4)0.026 (4)
O10.049 (3)0.072 (4)0.077 (3)−0.001 (5)0.039 (2)0.016 (5)
O20.055 (3)0.123 (7)0.054 (3)0.019 (4)0.032 (3)−0.027 (4)
O1W0.087 (4)0.070 (5)0.086 (4)0.004 (6)0.042 (4)0.014 (6)
O30.049 (3)0.067 (4)0.070 (4)0.021 (3)0.028 (3)0.007 (3)
O2W0.075 (4)0.112 (6)0.057 (3)0.004 (7)0.017 (3)−0.018 (7)
O3W0.059 (4)0.063 (4)0.082 (5)0.011 (3)0.028 (3)0.023 (4)
S10.0333 (7)0.0476 (10)0.0434 (8)0.0096 (7)0.0204 (7)−0.0016 (8)
Geometric parameters (Å, °) top
Ag1—O1W2.132 (7)C8—C91.384 (11)
Ag1—O2W2.139 (7)C8—H80.930
C1—C101.340 (10)C9—C101.404 (11)
C1—C21.427 (8)C9—H90.930
C1—S11.795 (6)C10—H100.930
C2—C31.413 (8)N1—H1A0.87 (5)
C2—C71.442 (8)N1—H2A0.92 (5)
C3—C41.332 (9)O1—S11.466 (10)
C3—H30.930O2—S11.456 (6)
C4—C51.436 (9)O1W—H1W0.91 (4)
C4—H40.930O1W—H2W0.86 (4)
C5—C61.373 (10)O3—S11.446 (6)
C5—N11.386 (10)O2W—H3W0.83 (4)
C6—C71.419 (10)O2W—H4W0.87 (4)
C6—H60.930O3W—H5W0.87 (5)
C7—C81.404 (10)O3W—H6W0.93 (4)
O1W—Ag1—O2W176.0 (6)C7—C8—H8119.3
C10—C1—C2121.6 (6)C8—C9—C10119.0 (7)
C10—C1—S1118.5 (5)C8—C9—H9120.5
C2—C1—S1119.8 (5)C10—C9—H9120.5
C3—C2—C1125.6 (5)C1—C10—C9121.5 (8)
C3—C2—C7116.9 (5)C1—C10—H10119.2
C1—C2—C7117.5 (5)C9—C10—H10119.2
C4—C3—C2122.5 (5)C5—N1—H1A125 (6)
C4—C3—H3118.7C5—N1—H2A120 (6)
C2—C3—H3118.7H1A—N1—H2A100 (6)
C3—C4—C5121.9 (6)Ag1—O1W—H1W126 (4)
C3—C4—H4119.1Ag1—O1W—H2W125 (6)
C5—C4—H4119.1H1W—O1W—H2W95 (5)
C6—C5—N1122.5 (6)Ag1—O2W—H3W108 (6)
C6—C5—C4117.5 (6)Ag1—O2W—H4W119 (6)
N1—C5—C4120.0 (7)H3W—O2W—H4W116 (7)
C5—C6—C7121.9 (6)H5W—O3W—H6W107 (6)
C5—C6—H6119.1O3—S1—O2113.8 (4)
C7—C6—H6119.1O3—S1—O1111.7 (4)
C8—C7—C6121.9 (6)O2—S1—O1113.0 (4)
C8—C7—C2118.8 (6)O3—S1—C1106.8 (3)
C6—C7—C2119.2 (6)O2—S1—C1105.1 (3)
C9—C8—C7121.5 (6)O1—S1—C1105.6 (3)
C9—C8—H8119.3
C10—C1—C2—C3−179.7 (6)C3—C2—C7—C6−3.3 (8)
S1—C1—C2—C30.4 (8)C1—C2—C7—C6177.9 (6)
C10—C1—C2—C7−1.0 (9)C6—C7—C8—C9−178.9 (7)
S1—C1—C2—C7179.1 (4)C2—C7—C8—C9−2.6 (10)
C1—C2—C3—C4−178.3 (6)C7—C8—C9—C103.1 (11)
C7—C2—C3—C43.0 (8)C2—C1—C10—C91.5 (11)
C2—C3—C4—C5−1.6 (10)S1—C1—C10—C9−178.5 (6)
C3—C4—C5—C60.4 (10)C8—C9—C10—C1−2.6 (12)
C3—C4—C5—N1−177.5 (7)C10—C1—S1—O3−1.7 (7)
N1—C5—C6—C7177.1 (8)C2—C1—S1—O3178.3 (5)
C4—C5—C6—C7−0.8 (10)C10—C1—S1—O2119.6 (6)
C5—C6—C7—C8178.7 (6)C2—C1—S1—O2−60.5 (6)
C5—C6—C7—C22.3 (10)C10—C1—S1—O1−120.7 (6)
C3—C2—C7—C8−179.7 (6)C2—C1—S1—O159.3 (6)
C1—C2—C7—C81.5 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3Wi0.87 (5)2.12 (5)2.980 (11)170 (8)
O3W—H5W···O10.87 (5)1.94 (5)2.746 (12)155 (8)
O3W—H6W···O2ii0.93 (4)1.89 (5)2.789 (9)160 (7)
O2W—H3W···O10.83 (4)2.43 (5)3.169 (8)150 (8)
O2W—H3W···O30.83 (4)2.54 (7)3.272 (13)149 (9)
O2W—H4W···O3Wiii0.87 (4)2.35 (6)3.177 (14)159 (9)
O1W—H2W···O2iv0.86 (4)2.48 (6)3.286 (12)155 (9)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z; (iii) −x+2, y−1/2, −z+1; (iv) x, y, z+1.
Table 1
Selected geometric parameters (Å, °) top
Ag1—O1W2.132 (7)Ag1—O2W2.139 (7)
O1W—Ag1—O2W176.0 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3Wi0.87 (5)2.12 (5)2.980 (11)170 (8)
O3W—H5W···O10.87 (5)1.94 (5)2.746 (12)155 (8)
O3W—H6W···O2ii0.93 (4)1.89 (5)2.789 (9)160 (7)
O2W—H3W···O10.83 (4)2.43 (5)3.169 (8)150 (8)
O2W—H3W···O30.83 (4)2.54 (7)3.272 (13)149 (9)
O2W—H4W···O3Wiii0.87 (4)2.35 (6)3.177 (14)159 (9)
O1W—H2W···O2iv0.86 (4)2.48 (6)3.286 (12)155 (9)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z; (iii) −x+2, y−1/2, −z+1; (iv) x, y, z+1.
Acknowledgements top

The authors thank the JiLin Agriculture, Science and Technology College (China) for support.

references
References top

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

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Shangguan, S.-P., Li, Y.-J. & Wu, H. (2007). Acta Cryst. E63, m1680–?.

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.