Acetato(1,10-phenanthroline-5,6-dione)silver(I) trihydrate.

In the structure of the title compound, [Ag(C(2)H(3)O(2))(C(12)H(6)N(2)O(2))]·3H(2)O, the Ag(I) atom is coordinated by both 1,10-phenanthroline-5,6-dione N atoms and one O atom from the acetate anion. The three water mol-ecules are involved in extensive hydrogen bonding to each other and to the acetate O and 1,10-phenanthroline-5,6-dione O atoms. In addition, there are weak C-H⋯O inter-actions.

Related literature

For related literature, see: Allen (2002 ▶); Armaroli (2001 ▶); Burrows et al. (1995 ▶); Calderazzo et al. (1999 ▶, 2002 ▶); Calucci et al. (2006 ▶); Fox et al. (1991 ▶); Galet et al. (2005 ▶); Hilt et al. (1997 ▶); Lei et al. (1996 ▶); Leschke et al. (2002 ▶); Ma et al. (2002 ▶); Okamura et al. (2006 ▶); Onuegbu et al. (2007 ▶); Pallenberg et al. (1997 ▶); Paramonov et al. (2003 ▶); Paw & Eisenberg (1997 ▶); Ruiz et al. (1999 ▶); Scaltrito et al. (2000 ▶); Shavaleev et al. (2003a ▶, 2003b ▶); Titze et al. (1997 ▶); Uche et al. (2007 ▶); Whitesides et al. (1991 ▶).

Experimental

Crystal data

[Ag(C2H3O2)(C12H6N2O2)]·3H2O

M = 431.15

Triclinic,

a = 6.6851 (11) Å

b = 9.6407 (17) Å

c = 12.818 (2) Å

α = 96.200 (2)°

β = 103.490 (2)°

γ = 104.629 (2)°

V = 765.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.36 mm−1

T = 103 (2) K

0.58 × 0.20 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.505, T max = 0.821

8724 measured reflections

4315 independent reflections

4105 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.068

S = 1.07

4315 reflections

243 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.28 e Å−3

Δρmin = −1.03 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000846/ci2544sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000846/ci2544Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C2H3O2)(C12H6N2O2)]·3H2O	Z = 2
Mr = 431.15	F000 = 432
Triclinic, P1	Dx = 1.872 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.6851 (11) Å	Cell parameters from 6131 reflections
b = 9.6407 (17) Å	θ = 2.0–30.6º
c = 12.818 (2) Å	µ = 1.36 mm−1
α = 96.200 (2)º	T = 103 (2) K
β = 103.490 (2)º	Needle, colorless
γ = 104.629 (2)º	0.58 × 0.20 × 0.15 mm
V = 765.0 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	4315 independent reflections
Radiation source: fine-focus sealed tube	4105 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 103(2) K	θmax = 30.7º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.505, Tmax = 0.821	k = −13→12
8724 measured reflections	l = −18→18

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0247P)2 + 0.7651P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.007
4315 reflections	Δρmax = 1.28 e Å−3
243 parameters	Δρmin = −1.03 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (2)

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
Ag	0.26396 (2)	0.328765 (18)	0.530264 (13)	0.02701 (7)
O1	0.2255 (3)	0.94093 (16)	0.31707 (14)	0.0314 (3)
O2	0.1697 (3)	0.73936 (18)	0.13835 (13)	0.0291 (3)
O1A	0.3458 (2)	0.19712 (16)	0.65468 (11)	0.0237 (3)
O2A	0.2011 (2)	0.34851 (16)	0.73262 (11)	0.0226 (3)
N1	0.2608 (3)	0.57669 (19)	0.53824 (13)	0.0212 (3)
N2	0.2125 (3)	0.37873 (18)	0.35977 (13)	0.0196 (3)
C1	0.2860 (3)	0.6716 (3)	0.62821 (16)	0.0271 (4)
H1A	0.2993	0.6381	0.6958	0.033*
C2	0.2936 (4)	0.8165 (3)	0.62682 (18)	0.0304 (5)
H2A	0.3128	0.8809	0.6923	0.036*
C3	0.2725 (3)	0.8656 (2)	0.52843 (18)	0.0267 (4)
H3A	0.2767	0.9642	0.5251	0.032*
C4	0.2451 (3)	0.7677 (2)	0.43425 (15)	0.0193 (3)
C5	0.2224 (3)	0.8171 (2)	0.32790 (17)	0.0212 (4)
C6	0.1923 (3)	0.7039 (2)	0.22726 (16)	0.0196 (3)
C7	0.1930 (3)	0.5547 (2)	0.24261 (14)	0.0168 (3)
C8	0.1725 (3)	0.4507 (2)	0.15281 (16)	0.0229 (4)
H8A	0.1591	0.4755	0.0823	0.028*
C9	0.1722 (3)	0.3120 (2)	0.16871 (17)	0.0265 (4)
H9A	0.1593	0.2394	0.1093	0.032*
C10	0.1909 (3)	0.2797 (2)	0.27241 (17)	0.0242 (4)
H10A	0.1884	0.1831	0.2824	0.029*
C11	0.2144 (3)	0.51492 (19)	0.34543 (14)	0.0154 (3)
C12	0.2408 (3)	0.6235 (2)	0.44269 (14)	0.0166 (3)
C1A	0.2816 (3)	0.2439 (2)	0.73360 (15)	0.0187 (3)
C2A	0.3012 (4)	0.1690 (3)	0.83090 (17)	0.0290 (4)
H2AA	0.1579	0.1141	0.8334	0.043*
H2AB	0.3701	0.2419	0.8976	0.043*
H2AC	0.3883	0.1020	0.8251	0.043*
O1W	0.2028 (3)	0.98250 (18)	0.03879 (14)	0.0279 (3)
H1W1	0.190 (5)	0.927 (3)	0.081 (2)	0.045 (9)*
H1W2	0.111 (9)	1.023 (8)	0.026 (7)	0.18 (3)*
O2W	0.3820 (3)	0.8231 (2)	0.89715 (14)	0.0336 (4)
H2W1	0.315 (6)	0.858 (4)	0.931 (3)	0.072 (13)*
H2W2	0.505 (4)	0.874 (5)	0.910 (4)	0.097 (17)*
O3W	0.3387 (3)	0.5397 (2)	0.93172 (14)	0.0354 (4)
H3W1	0.296 (6)	0.483 (3)	0.874 (2)	0.053 (10)*
H3W2	0.359 (9)	0.627 (3)	0.927 (5)	0.12 (2)*

	U11	U22	U33	U12	U13	U23
Ag	0.02657 (10)	0.03085 (11)	0.02929 (10)	0.01137 (7)	0.00869 (6)	0.01938 (7)
O1	0.0345 (8)	0.0148 (7)	0.0441 (9)	0.0076 (6)	0.0070 (7)	0.0094 (6)
O2	0.0393 (8)	0.0280 (8)	0.0268 (7)	0.0127 (7)	0.0137 (6)	0.0158 (6)
O1A	0.0339 (8)	0.0221 (7)	0.0216 (6)	0.0145 (6)	0.0113 (6)	0.0081 (5)
O2A	0.0278 (7)	0.0211 (7)	0.0230 (6)	0.0120 (6)	0.0078 (5)	0.0071 (5)
N1	0.0188 (7)	0.0254 (8)	0.0194 (7)	0.0053 (6)	0.0055 (6)	0.0056 (6)
N2	0.0197 (7)	0.0153 (7)	0.0238 (7)	0.0055 (6)	0.0047 (6)	0.0061 (6)
C1	0.0220 (9)	0.0387 (12)	0.0190 (8)	0.0060 (8)	0.0065 (7)	0.0020 (8)
C2	0.0280 (10)	0.0340 (12)	0.0245 (9)	0.0050 (9)	0.0077 (8)	−0.0069 (8)
C3	0.0261 (10)	0.0194 (9)	0.0318 (10)	0.0047 (8)	0.0076 (8)	−0.0026 (8)
C4	0.0180 (8)	0.0162 (8)	0.0225 (8)	0.0039 (6)	0.0048 (6)	0.0026 (7)
C5	0.0192 (8)	0.0151 (8)	0.0290 (9)	0.0043 (7)	0.0058 (7)	0.0061 (7)
C6	0.0201 (8)	0.0170 (8)	0.0247 (8)	0.0061 (7)	0.0083 (7)	0.0094 (7)
C7	0.0178 (8)	0.0149 (8)	0.0187 (8)	0.0049 (6)	0.0054 (6)	0.0050 (6)
C8	0.0242 (9)	0.0249 (10)	0.0199 (8)	0.0077 (7)	0.0062 (7)	0.0027 (7)
C9	0.0294 (10)	0.0214 (9)	0.0266 (9)	0.0079 (8)	0.0058 (8)	−0.0025 (7)
C10	0.0252 (9)	0.0143 (8)	0.0323 (10)	0.0064 (7)	0.0054 (8)	0.0035 (7)
C11	0.0141 (7)	0.0138 (8)	0.0181 (7)	0.0036 (6)	0.0041 (6)	0.0044 (6)
C12	0.0127 (7)	0.0171 (8)	0.0191 (8)	0.0030 (6)	0.0038 (6)	0.0041 (6)
C1A	0.0190 (8)	0.0174 (8)	0.0189 (8)	0.0038 (6)	0.0043 (6)	0.0044 (6)
C2A	0.0376 (11)	0.0334 (11)	0.0232 (9)	0.0173 (9)	0.0103 (8)	0.0142 (8)
O1W	0.0313 (8)	0.0228 (7)	0.0339 (8)	0.0100 (6)	0.0103 (6)	0.0146 (6)
O2W	0.0390 (9)	0.0294 (9)	0.0304 (8)	0.0073 (7)	0.0084 (7)	0.0045 (7)
O3W	0.0431 (10)	0.0308 (9)	0.0279 (8)	0.0114 (8)	0.0049 (7)	−0.0039 (7)

Ag—O1A	2.1987 (14)	C6—C7	1.474 (3)
Ag—N2	2.2554 (17)	C7—C11	1.398 (2)
Ag—N1	2.3870 (18)	C7—C8	1.399 (3)
O1—C5	1.212 (2)	C8—C9	1.373 (3)
O2—C6	1.212 (2)	C8—H8A	0.95
O1A—C1A	1.270 (2)	C9—C10	1.383 (3)
O2A—C1A	1.257 (2)	C9—H9A	0.95
N1—C12	1.340 (2)	C10—H10A	0.95
N1—C1	1.341 (3)	C11—C12	1.484 (2)
N2—C11	1.343 (2)	C1A—C2A	1.504 (3)
N2—C10	1.346 (3)	C2A—H2AA	0.98
C1—C2	1.387 (3)	C2A—H2AB	0.98
C1—H1A	0.95	C2A—H2AC	0.98
C2—C3	1.384 (3)	O1W—H1W1	0.80 (2)
C2—H2A	0.95	O1W—H1W2	0.81 (2)
C3—C4	1.395 (3)	O2W—H2W1	0.79 (2)
C3—H3A	0.95	O2W—H2W2	0.81 (2)
C4—C12	1.399 (3)	O3W—H3W1	0.82 (2)
C4—C5	1.479 (3)	O3W—H3W2	0.82 (2)
C5—C6	1.536 (3)
O1A—Ag—N2	153.49 (6)	C11—C7—C6	121.26 (16)
O1A—Ag—N1	133.64 (6)	C8—C7—C6	119.55 (17)
N2—Ag—N1	71.57 (6)	C9—C8—C7	118.65 (18)
C1A—O1A—Ag	104.47 (12)	C9—C8—H8A	120.7
C12—N1—C1	118.63 (18)	C7—C8—H8A	120.7
C12—N1—Ag	114.93 (12)	C8—C9—C10	119.10 (18)
C1—N1—Ag	126.37 (15)	C8—C9—H9A	120.5
C11—N2—C10	118.50 (17)	C10—C9—H9A	120.5
C11—N2—Ag	118.68 (12)	N2—C10—C9	122.98 (19)
C10—N2—Ag	122.73 (13)	N2—C10—H10A	118.5
N1—C1—C2	122.9 (2)	C9—C10—H10A	118.5
N1—C1—H1A	118.6	N2—C11—C7	121.57 (16)
C2—C1—H1A	118.6	N2—C11—C12	117.94 (16)
C3—C2—C1	118.84 (19)	C7—C11—C12	120.49 (16)
C3—C2—H2A	120.6	N1—C12—C4	122.01 (17)
C1—C2—H2A	120.6	N1—C12—C11	116.75 (17)
C2—C3—C4	118.8 (2)	C4—C12—C11	121.23 (16)
C2—C3—H3A	120.6	O2A—C1A—O1A	122.59 (17)
C4—C3—H3A	120.6	O2A—C1A—C2A	119.33 (17)
C3—C4—C12	118.85 (18)	O1A—C1A—C2A	118.08 (17)
C3—C4—C5	120.01 (18)	C1A—C2A—H2AA	109.5
C12—C4—C5	121.14 (17)	C1A—C2A—H2AB	109.5
O1—C5—C4	123.23 (19)	H2AA—C2A—H2AB	109.5
O1—C5—C6	119.30 (18)	C1A—C2A—H2AC	109.5
C4—C5—C6	117.47 (16)	H2AA—C2A—H2AC	109.5
O2—C6—C7	122.05 (18)	H2AB—C2A—H2AC	109.5
O2—C6—C5	119.57 (18)	H1W1—O1W—H1W2	115 (6)
C7—C6—C5	118.39 (16)	H2W1—O2W—H2W2	112 (5)
C11—C7—C8	119.19 (17)	H3W1—O3W—H3W2	115 (5)
N2—Ag—O1A—C1A	−165.35 (13)	C11—C7—C8—C9	0.6 (3)
N1—Ag—O1A—C1A	35.72 (16)	C6—C7—C8—C9	−179.60 (18)
O1A—Ag—N1—C12	167.44 (11)	C7—C8—C9—C10	0.3 (3)
N2—Ag—N1—C12	−2.82 (12)	C11—N2—C10—C9	0.5 (3)
O1A—Ag—N1—C1	−9.46 (19)	Ag—N2—C10—C9	−176.01 (15)
N2—Ag—N1—C1	−179.72 (17)	C8—C9—C10—N2	−0.9 (3)
O1A—Ag—N2—C11	−161.23 (13)	C10—N2—C11—C7	0.5 (3)
N1—Ag—N2—C11	2.85 (13)	Ag—N2—C11—C7	177.12 (13)
O1A—Ag—N2—C10	15.3 (2)	C10—N2—C11—C12	−179.30 (16)
N1—Ag—N2—C10	179.36 (17)	Ag—N2—C11—C12	−2.6 (2)
C12—N1—C1—C2	−0.3 (3)	C8—C7—C11—N2	−1.0 (3)
Ag—N1—C1—C2	176.46 (15)	C6—C7—C11—N2	179.17 (16)
N1—C1—C2—C3	0.5 (3)	C8—C7—C11—C12	178.76 (16)
C1—C2—C3—C4	−0.2 (3)	C6—C7—C11—C12	−1.1 (3)
C2—C3—C4—C12	−0.3 (3)	C1—N1—C12—C4	−0.2 (3)
C2—C3—C4—C5	−179.94 (19)	Ag—N1—C12—C4	−177.32 (13)
C3—C4—C5—O1	−0.3 (3)	C1—N1—C12—C11	179.68 (16)
C12—C4—C5—O1	−179.91 (19)	Ag—N1—C12—C11	2.52 (19)
C3—C4—C5—C6	−179.92 (17)	C3—C4—C12—N1	0.5 (3)
C12—C4—C5—C6	0.4 (3)	C5—C4—C12—N1	−179.88 (17)
O1—C5—C6—O2	−0.8 (3)	C3—C4—C12—C11	−179.36 (17)
C4—C5—C6—O2	178.84 (18)	C5—C4—C12—C11	0.3 (3)
O1—C5—C6—C7	178.90 (18)	N2—C11—C12—N1	−0.1 (2)
C4—C5—C6—C7	−1.4 (2)	C7—C11—C12—N1	−179.85 (16)
O2—C6—C7—C11	−178.52 (18)	N2—C11—C12—C4	179.77 (16)
C5—C6—C7—C11	1.8 (3)	C7—C11—C12—C4	0.0 (3)
O2—C6—C7—C8	1.7 (3)	Ag—O1A—C1A—O2A	−3.1 (2)
C5—C6—C7—C8	−178.06 (17)	Ag—O1A—C1A—C2A	176.13 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.80 (2)	2.01 (2)	2.773 (2)	158 (3)
O1W—H1W2···O1Wi	0.81 (2)	2.05 (4)	2.781 (3)	151 (7)
O2W—H2W1···O1Wii	0.79 (2)	2.12 (2)	2.904 (2)	168 (4)
O2W—H2W2···O1Wiii	0.81 (2)	2.00 (2)	2.805 (3)	170 (5)
O3W—H3W1···O2A	0.82 (2)	1.97 (2)	2.791 (2)	178 (4)
O3W—H3W2···O2W	0.82 (2)	1.95 (2)	2.769 (3)	172 (6)
C3—H3A···O1Aiv	0.95	2.52	3.286 (3)	138
C8—H8A···O3Wv	0.95	2.55	3.393 (3)	148
C10—H10A···O1vi	0.95	2.48	3.431 (3)	174

Ag—O1A	2.1987 (14)
Ag—N2	2.2554 (17)
Ag—N1	2.3870 (18)

O1A—Ag—N2	153.49 (6)
O1A—Ag—N1	133.64 (6)
N2—Ag—N1	71.57 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2	0.80 (2)	2.01 (2)	2.773 (2)	158 (3)
O1W—H1W2⋯O1Wi	0.81 (2)	2.05 (4)	2.781 (3)	151 (7)
O2W—H2W1⋯O1Wii	0.79 (2)	2.12 (2)	2.904 (2)	168 (4)
O2W—H2W2⋯O1Wiii	0.81 (2)	2.00 (2)	2.805 (3)	170 (5)
O3W—H3W1⋯O2A	0.82 (2)	1.97 (2)	2.791 (2)	178 (4)
O3W—H3W2⋯O2W	0.82 (2)	1.95 (2)	2.769 (3)	172 (6)
C3—H3A⋯O1Aiv	0.95	2.52	3.286 (3)	138
C8—H8A⋯O3Wv	0.95	2.55	3.393 (3)	148
C10—H10A⋯O1vi	0.95	2.48	3.431 (3)	174

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .