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

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.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.033
• wR factor = 0.140
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1W    ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Ag1
PLAT245_ALERT_2_C U(iso) H1W     Smaller than U(eq) O1W     by ...       0.02 AngSq
PLAT245_ALERT_2_C U(iso) H2W     Smaller than U(eq) O1W     by ...       0.02 AngSq
PLAT245_ALERT_2_C U(iso) H3W     Smaller than U(eq) O2W     by ...       0.03 AngSq
PLAT245_ALERT_2_C U(iso) H4W     Smaller than U(eq) O2W     by ...       0.03 AngSq
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H2A    ...          ?

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           28.30
           From the CIF: _reflns_number_total               2177
           Count of symmetry unique reflns         1795
           Completeness (_total/calc)            121.28%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       382
           Fraction of Friedel pairs measured     0.213
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1         (1)       0.91
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         14

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

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

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S1. Comment

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—O_water 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

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).

S2. Experimental

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.

S3. Refinement

All H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and U_iso(H)= 1.2U_eq(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 U_iso(H) = 0.06 Ų. 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 U_iso(H) = 0.06 Ų.

Computing details

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

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	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

Crystal data

[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) Å^3	0.25 × 0.23 × 0.20 mm
Z = 2

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0984P)^2] where P = (Fo^2 + 2Fc^2)/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)

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3W^i	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···O2^ii	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···O3W^iii	0.87 (4)	2.35 (6)	3.177 (14)	159 (9)
O1W—H2W···O2^iv	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.