Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036495/cf2112sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036495/cf2112Isup2.hkl |
CCDC reference: 630591
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.
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.
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).
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).
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.
[Ag(H2O)2](C10H8NO3S)·H2O | F(000) = 384 |
Mr = 384.15 | Dx = 1.872 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2177 reflections |
a = 8.8780 (11) Å | θ = 2.4–28.3° |
b = 9.0141 (11) Å | µ = 1.65 mm−1 |
c = 9.5576 (12) Å | T = 292 K |
β = 116.989 (2)° | Block, white |
V = 681.57 (15) Å3 | 0.25 × 0.23 × 0.20 mm |
Z = 2 |
Bruker SMART APEX CCD diffractometer | 2177 independent reflections |
Radiation source: fine-focus sealed tube | 1740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.652, Tmax = 0.718 | k = −11→6 |
4251 measured reflections | l = −12→12 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H 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 reflections | Δρmax = 0.49 e Å−3 |
196 parameters | Δρmin = −0.44 e Å−3 |
14 restraints | Absolute structure: Flack (1983), with 482 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.08 (6) |
[Ag(H2O)2](C10H8NO3S)·H2O | V = 681.57 (15) Å3 |
Mr = 384.15 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.8780 (11) Å | µ = 1.65 mm−1 |
b = 9.0141 (11) Å | T = 292 K |
c = 9.5576 (12) Å | 0.25 × 0.23 × 0.20 mm |
β = 116.989 (2)° |
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 = 0.718 | Rint = 0.052 |
4251 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.141 | Δρmax = 0.49 e Å−3 |
S = 1.01 | Δρmin = −0.44 e Å−3 |
2177 reflections | Absolute structure: Flack (1983), with 482 Friedel pairs |
196 parameters | Absolute structure parameter: −0.08 (6) |
14 restraints |
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 | ||
Ag1 | 0.80067 (8) | 0.46498 (10) | 0.74795 (7) | 0.0652 (3) | |
C1 | 0.5086 (7) | 0.3207 (8) | 0.3324 (7) | 0.0294 (12) | |
C2 | 0.3669 (7) | 0.4157 (7) | 0.2499 (7) | 0.0281 (12) | |
C3 | 0.3425 (7) | 0.5079 (7) | 0.1217 (7) | 0.0313 (14) | |
H3 | 0.4227 | 0.5065 | 0.0844 | 0.038* | |
C4 | 0.2089 (7) | 0.5968 (8) | 0.0524 (7) | 0.0327 (13) | |
H4 | 0.2003 | 0.6571 | −0.0299 | 0.039* | |
C5 | 0.0779 (8) | 0.6023 (8) | 0.1009 (8) | 0.0358 (14) | |
C6 | 0.0952 (8) | 0.5125 (8) | 0.2234 (7) | 0.0366 (14) | |
H6 | 0.0127 | 0.5150 | 0.2579 | 0.044* | |
C7 | 0.2355 (8) | 0.4159 (8) | 0.2989 (7) | 0.0325 (13) | |
C8 | 0.2550 (8) | 0.3263 (9) | 0.4263 (8) | 0.0395 (15) | |
H8 | 0.1729 | 0.3289 | 0.4613 | 0.047* | |
C9 | 0.3937 (10) | 0.2342 (9) | 0.5009 (9) | 0.0461 (18) | |
H9 | 0.4022 | 0.1719 | 0.5817 | 0.055* | |
C10 | 0.5212 (11) | 0.2362 (9) | 0.4525 (9) | 0.0454 (17) | |
H10 | 0.6167 | 0.1774 | 0.5051 | 0.055* | |
N1 | −0.0621 (9) | 0.6922 (10) | 0.0216 (10) | 0.063 (2) | |
O1 | 0.7407 (6) | 0.4647 (11) | 0.2927 (7) | 0.0617 (14) | |
O2 | 0.5950 (8) | 0.2620 (10) | 0.1133 (7) | 0.075 (2) | |
O1W | 0.6141 (10) | 0.4549 (14) | 0.8300 (9) | 0.0801 (18) | |
O3 | 0.8013 (7) | 0.2118 (8) | 0.3828 (8) | 0.0615 (16) | |
O2W | 0.9824 (9) | 0.4600 (17) | 0.6590 (8) | 0.086 (2) | |
O3W | 0.7058 (8) | 0.7430 (8) | 0.1647 (9) | 0.0691 (18) | |
S1 | 0.6754 (2) | 0.3129 (2) | 0.2756 (2) | 0.0403 (4) | |
H1A | −0.137 (9) | 0.713 (10) | 0.053 (10) | 0.060* | |
H1W | 0.543 (9) | 0.530 (8) | 0.825 (9) | 0.060* | |
H2A | −0.050 (11) | 0.783 (7) | −0.014 (12) | 0.060* | |
H2W | 0.632 (12) | 0.426 (9) | 0.922 (7) | 0.060* | |
H3W | 0.935 (9) | 0.428 (10) | 0.568 (6) | 0.060* | |
H4W | 1.082 (7) | 0.423 (10) | 0.718 (8) | 0.060* | |
H5W | 0.696 (11) | 0.649 (6) | 0.176 (10) | 0.060* | |
H6W | 0.616 (8) | 0.770 (9) | 0.069 (7) | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0660 (4) | 0.0669 (4) | 0.0606 (4) | −0.0042 (4) | 0.0267 (3) | 0.0046 (4) |
C1 | 0.025 (3) | 0.028 (3) | 0.031 (3) | 0.006 (3) | 0.010 (2) | −0.004 (3) |
C2 | 0.025 (3) | 0.025 (3) | 0.033 (3) | −0.006 (2) | 0.012 (2) | −0.006 (2) |
C3 | 0.028 (3) | 0.036 (4) | 0.031 (3) | −0.006 (2) | 0.014 (2) | −0.004 (2) |
C4 | 0.032 (3) | 0.035 (3) | 0.031 (3) | −0.004 (3) | 0.014 (2) | 0.000 (3) |
C5 | 0.034 (3) | 0.034 (3) | 0.038 (3) | 0.005 (3) | 0.016 (3) | −0.005 (3) |
C6 | 0.029 (3) | 0.039 (4) | 0.047 (3) | −0.008 (2) | 0.021 (3) | −0.005 (3) |
C7 | 0.032 (3) | 0.034 (3) | 0.032 (3) | −0.004 (2) | 0.015 (2) | −0.005 (2) |
C8 | 0.039 (3) | 0.042 (4) | 0.043 (3) | −0.002 (3) | 0.024 (3) | −0.002 (3) |
C9 | 0.053 (4) | 0.039 (4) | 0.043 (4) | 0.001 (3) | 0.020 (4) | 0.016 (3) |
C10 | 0.050 (4) | 0.041 (4) | 0.040 (4) | −0.004 (3) | 0.015 (3) | 0.004 (3) |
N1 | 0.046 (4) | 0.069 (5) | 0.074 (5) | 0.020 (4) | 0.028 (4) | 0.026 (4) |
O1 | 0.049 (3) | 0.072 (4) | 0.077 (3) | −0.001 (5) | 0.039 (2) | 0.016 (5) |
O2 | 0.055 (3) | 0.123 (7) | 0.054 (3) | 0.019 (4) | 0.032 (3) | −0.027 (4) |
O1W | 0.087 (4) | 0.070 (5) | 0.086 (4) | 0.004 (6) | 0.042 (4) | 0.014 (6) |
O3 | 0.049 (3) | 0.067 (4) | 0.070 (4) | 0.021 (3) | 0.028 (3) | 0.007 (3) |
O2W | 0.075 (4) | 0.112 (6) | 0.057 (3) | 0.004 (7) | 0.017 (3) | −0.018 (7) |
O3W | 0.059 (4) | 0.063 (4) | 0.082 (5) | 0.011 (3) | 0.028 (3) | 0.023 (4) |
S1 | 0.0333 (7) | 0.0476 (10) | 0.0434 (8) | 0.0096 (7) | 0.0204 (7) | −0.0016 (8) |
Ag1—O1W | 2.132 (7) | C8—C9 | 1.384 (11) |
Ag1—O2W | 2.139 (7) | C8—H8 | 0.930 |
C1—C10 | 1.340 (10) | C9—C10 | 1.404 (11) |
C1—C2 | 1.427 (8) | C9—H9 | 0.930 |
C1—S1 | 1.795 (6) | C10—H10 | 0.930 |
C2—C3 | 1.413 (8) | N1—H1A | 0.87 (5) |
C2—C7 | 1.442 (8) | N1—H2A | 0.92 (5) |
C3—C4 | 1.332 (9) | O1—S1 | 1.466 (10) |
C3—H3 | 0.930 | O2—S1 | 1.456 (6) |
C4—C5 | 1.436 (9) | O1W—H1W | 0.91 (4) |
C4—H4 | 0.930 | O1W—H2W | 0.86 (4) |
C5—C6 | 1.373 (10) | O3—S1 | 1.446 (6) |
C5—N1 | 1.386 (10) | O2W—H3W | 0.83 (4) |
C6—C7 | 1.419 (10) | O2W—H4W | 0.87 (4) |
C6—H6 | 0.930 | O3W—H5W | 0.87 (5) |
C7—C8 | 1.404 (10) | O3W—H6W | 0.93 (4) |
O1W—Ag1—O2W | 176.0 (6) | C7—C8—H8 | 119.3 |
C10—C1—C2 | 121.6 (6) | C8—C9—C10 | 119.0 (7) |
C10—C1—S1 | 118.5 (5) | C8—C9—H9 | 120.5 |
C2—C1—S1 | 119.8 (5) | C10—C9—H9 | 120.5 |
C3—C2—C1 | 125.6 (5) | C1—C10—C9 | 121.5 (8) |
C3—C2—C7 | 116.9 (5) | C1—C10—H10 | 119.2 |
C1—C2—C7 | 117.5 (5) | C9—C10—H10 | 119.2 |
C4—C3—C2 | 122.5 (5) | C5—N1—H1A | 125 (6) |
C4—C3—H3 | 118.7 | C5—N1—H2A | 120 (6) |
C2—C3—H3 | 118.7 | H1A—N1—H2A | 100 (6) |
C3—C4—C5 | 121.9 (6) | Ag1—O1W—H1W | 126 (4) |
C3—C4—H4 | 119.1 | Ag1—O1W—H2W | 125 (6) |
C5—C4—H4 | 119.1 | H1W—O1W—H2W | 95 (5) |
C6—C5—N1 | 122.5 (6) | Ag1—O2W—H3W | 108 (6) |
C6—C5—C4 | 117.5 (6) | Ag1—O2W—H4W | 119 (6) |
N1—C5—C4 | 120.0 (7) | H3W—O2W—H4W | 116 (7) |
C5—C6—C7 | 121.9 (6) | H5W—O3W—H6W | 107 (6) |
C5—C6—H6 | 119.1 | O3—S1—O2 | 113.8 (4) |
C7—C6—H6 | 119.1 | O3—S1—O1 | 111.7 (4) |
C8—C7—C6 | 121.9 (6) | O2—S1—O1 | 113.0 (4) |
C8—C7—C2 | 118.8 (6) | O3—S1—C1 | 106.8 (3) |
C6—C7—C2 | 119.2 (6) | O2—S1—C1 | 105.1 (3) |
C9—C8—C7 | 121.5 (6) | O1—S1—C1 | 105.6 (3) |
C9—C8—H8 | 119.3 | ||
C10—C1—C2—C3 | −179.7 (6) | C3—C2—C7—C6 | −3.3 (8) |
S1—C1—C2—C3 | 0.4 (8) | C1—C2—C7—C6 | 177.9 (6) |
C10—C1—C2—C7 | −1.0 (9) | C6—C7—C8—C9 | −178.9 (7) |
S1—C1—C2—C7 | 179.1 (4) | C2—C7—C8—C9 | −2.6 (10) |
C1—C2—C3—C4 | −178.3 (6) | C7—C8—C9—C10 | 3.1 (11) |
C7—C2—C3—C4 | 3.0 (8) | C2—C1—C10—C9 | 1.5 (11) |
C2—C3—C4—C5 | −1.6 (10) | S1—C1—C10—C9 | −178.5 (6) |
C3—C4—C5—C6 | 0.4 (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—C7 | 177.1 (8) | C2—C1—S1—O3 | 178.3 (5) |
C4—C5—C6—C7 | −0.8 (10) | C10—C1—S1—O2 | 119.6 (6) |
C5—C6—C7—C8 | 178.7 (6) | C2—C1—S1—O2 | −60.5 (6) |
C5—C6—C7—C2 | 2.3 (10) | C10—C1—S1—O1 | −120.7 (6) |
C3—C2—C7—C8 | −179.7 (6) | C2—C1—S1—O1 | 59.3 (6) |
C1—C2—C7—C8 | 1.5 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3Wi | 0.87 (5) | 2.12 (5) | 2.980 (11) | 170 (8) |
O3W—H5W···O1 | 0.87 (5) | 1.94 (5) | 2.746 (12) | 155 (8) |
O3W—H6W···O2ii | 0.93 (4) | 1.89 (5) | 2.789 (9) | 160 (7) |
O2W—H3W···O1 | 0.83 (4) | 2.43 (5) | 3.169 (8) | 150 (8) |
O2W—H3W···O3 | 0.83 (4) | 2.54 (7) | 3.272 (13) | 149 (9) |
O2W—H4W···O3Wiii | 0.87 (4) | 2.35 (6) | 3.177 (14) | 159 (9) |
O1W—H2W···O2iv | 0.86 (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. |
Experimental details
Crystal data | |
Chemical formula | [Ag(H2O)2](C10H8NO3S)·H2O |
Mr | 384.15 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 292 |
a, b, c (Å) | 8.8780 (11), 9.0141 (11), 9.5576 (12) |
β (°) | 116.989 (2) |
V (Å3) | 681.57 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.65 |
Crystal size (mm) | 0.25 × 0.23 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.652, 0.718 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4251, 2177, 1740 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.141, 1.01 |
No. of reflections | 2177 |
No. of parameters | 196 |
No. of restraints | 14 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.49, −0.44 |
Absolute structure | Flack (1983), with 482 Friedel pairs |
Absolute structure parameter | −0.08 (6) |
Computer programs: SMART (Bruker, 1997, SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3Wi | 0.87 (5) | 2.12 (5) | 2.980 (11) | 170 (8) |
O3W—H5W···O1 | 0.87 (5) | 1.94 (5) | 2.746 (12) | 155 (8) |
O3W—H6W···O2ii | 0.93 (4) | 1.89 (5) | 2.789 (9) | 160 (7) |
O2W—H3W···O1 | 0.83 (4) | 2.43 (5) | 3.169 (8) | 150 (8) |
O2W—H3W···O3 | 0.83 (4) | 2.54 (7) | 3.272 (13) | 149 (9) |
O2W—H4W···O3Wiii | 0.87 (4) | 2.35 (6) | 3.177 (14) | 159 (9) |
O1W—H2W···O2iv | 0.86 (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. |
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).