Bis[bis(1H-imidazole-κN)silver(I)] naphthalene-1,5-disulfonate.

The title compound, [Ag(C(3)H(4)N(2))(2)](2)(C(10)H(6)O(6)S(2)), exists in the form of isolated cations and anions with electrostatic inter-action between them. The Ag atom is two-coordinated by the N atoms of two crystallographically independent imidazole mol-ecules. The naphthalene-1,5-disulfonate anion is located on a crystallographic center of symmetry. The cations and anions are connected through inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Côté & Shimizu (2003 ▶, 2004 ▶); Cai (2004 ▶); Cai et al. (2001 ▶); Chen et al. (2001 ▶, 2002 ▶); Dalrymple & Shimizu (2002 ▶); Lian et al. (2007 ▶); Liu et al. (2006 ▶); Reddy et al. (2003 ▶); Shimizu et al. (1999 ▶); Zhou et al. (2004 ▶).

Experimental

Crystal data

[Ag(C3H4N2)2]2(C10H6O6S2)

M = 774.36

Triclinic,

a = 8.6491 (11) Å

b = 9.0196 (12) Å

c = 10.2620 (13) Å

α = 65.286 (2)°

β = 76.311 (2)°

γ = 66.791 (2)°

V = 665.89 (15) Å3

Z = 1

Mo Kα radiation

μ = 1.68 mm−1

T = 293 (2) K

0.50 × 0.30 × 0.13 mm

Data collection

Bruker Smart 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.487, T max = 0.811

4267 measured reflections

2962 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.063

S = 0.93

2962 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.67 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536808006855/rk2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006855/rk2068Isup2.hkl

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

[Ag(C3H4N2)2](C10H6O6S2)	Z = 1
Mr = 774.36	F000 = 384
Triclinic, P1	Dx = 1.931 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.6491 (11) Å	Cell parameters from 2962 reflections
b = 9.0196 (12) Å	θ = 2.2–27.5º
c = 10.2620 (13) Å	µ = 1.68 mm−1
α = 65.286 (2)º	T = 293 (2) K
β = 76.311 (2)º	Block, colourless
γ = 66.791 (2)º	0.50 × 0.30 × 0.13 mm
V = 665.89 (15) Å3

Bruker Smart 1000 CCD diffractometer	2962 independent reflections
Radiation source: Fine–focus sealed tube	2417 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.010
T = 293(2) K	θmax = 27.5º
φ– and ω–scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −11→9
Tmin = 0.487, Tmax = 0.811	k = −11→10
4267 measured reflections	l = −13→13

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0388P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
2962 reflections	Δρmax = 0.70 e Å−3
181 parameters	Δρmin = −0.67 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.27879 (2)	1.03409 (3)	0.79027 (2)	0.05010 (9)
S1	0.26541 (6)	0.60865 (7)	0.78924 (5)	0.02831 (12)
O1	0.2153 (2)	0.7948 (2)	0.71897 (19)	0.0442 (4)
O2	0.1257 (2)	0.5487 (2)	0.87280 (17)	0.0403 (4)
O3	0.40789 (19)	0.5352 (2)	0.87452 (17)	0.0394 (4)
N1	0.0163 (2)	1.1487 (3)	0.8293 (2)	0.0375 (5)
N2	−0.2347 (3)	1.2925 (3)	0.9009 (2)	0.0432 (5)
H2A	−0.3130	1.3607	0.9392	0.052*
N3	0.5433 (3)	0.9312 (3)	0.7528 (2)	0.0452 (5)
N4	0.8038 (3)	0.7606 (3)	0.7855 (3)	0.0526 (6)
H4A	0.8907	0.6797	0.8272	0.063*
C1	−0.0695 (3)	1.2583 (3)	0.8957 (3)	0.0400 (6)
H1A	−0.0211	1.3053	0.9338	0.048*
C2	−0.2576 (3)	1.2010 (4)	0.8351 (3)	0.0478 (6)
H2B	−0.3600	1.1994	0.8230	0.057*
C3	−0.1029 (3)	1.1132 (3)	0.7907 (3)	0.0441 (6)
H3A	−0.0801	1.0397	0.7415	0.053*
C4	0.6465 (4)	0.8000 (4)	0.8461 (3)	0.0521 (7)
H4B	0.6136	0.7427	0.9413	0.063*
C5	0.8032 (3)	0.8703 (4)	0.6468 (3)	0.0500 (7)
H5A	0.8953	0.8729	0.5783	0.060*
C6	0.6423 (3)	0.9747 (4)	0.6280 (3)	0.0454 (6)
H6A	0.6041	1.0637	0.5423	0.054*
C7	0.3281 (2)	0.5262 (3)	0.6470 (2)	0.0261 (4)
C8	0.2202 (3)	0.4654 (3)	0.6223 (2)	0.0315 (5)
H8A	0.1202	0.4645	0.6810	0.038*
C9	0.2585 (3)	0.4046 (3)	0.5098 (3)	0.0356 (5)
H9A	0.1838	0.3637	0.4942	0.043*
C10	0.4037 (3)	0.4044 (3)	0.4227 (2)	0.0303 (5)
H10A	0.4281	0.3617	0.3492	0.036*
C11	0.5190 (2)	0.4687 (3)	0.4427 (2)	0.0244 (4)

	U11	U22	U33	U12	U13	U23
Ag1	0.02873 (11)	0.04781 (14)	0.06505 (16)	−0.00509 (8)	−0.00059 (8)	−0.02144 (11)
S1	0.0227 (2)	0.0346 (3)	0.0263 (3)	−0.0032 (2)	0.00093 (19)	−0.0173 (2)
O1	0.0487 (10)	0.0341 (9)	0.0476 (10)	−0.0029 (8)	−0.0031 (8)	−0.0236 (8)
O2	0.0293 (8)	0.0570 (11)	0.0346 (8)	−0.0124 (8)	0.0063 (7)	−0.0233 (8)
O3	0.0279 (8)	0.0556 (11)	0.0329 (8)	−0.0057 (7)	−0.0030 (6)	−0.0220 (8)
N1	0.0316 (10)	0.0353 (11)	0.0465 (11)	−0.0088 (8)	0.0017 (8)	−0.0205 (9)
N2	0.0362 (11)	0.0375 (11)	0.0476 (12)	−0.0032 (9)	0.0050 (9)	−0.0208 (10)
N3	0.0304 (11)	0.0365 (11)	0.0600 (14)	−0.0080 (9)	−0.0059 (10)	−0.0113 (10)
N4	0.0325 (11)	0.0442 (13)	0.0836 (18)	−0.0012 (9)	−0.0170 (11)	−0.0300 (13)
C1	0.0413 (13)	0.0409 (14)	0.0435 (13)	−0.0144 (11)	0.0025 (10)	−0.0232 (11)
C2	0.0337 (13)	0.0473 (15)	0.0614 (17)	−0.0097 (11)	−0.0081 (12)	−0.0203 (14)
C3	0.0415 (14)	0.0414 (14)	0.0579 (16)	−0.0109 (11)	−0.0037 (12)	−0.0291 (13)
C4	0.0435 (15)	0.0431 (15)	0.0591 (17)	−0.0119 (12)	−0.0076 (13)	−0.0094 (13)
C5	0.0403 (15)	0.0558 (17)	0.0661 (18)	−0.0174 (13)	0.0001 (13)	−0.0347 (16)
C6	0.0423 (14)	0.0419 (14)	0.0541 (16)	−0.0138 (12)	−0.0073 (12)	−0.0180 (13)
C7	0.0245 (10)	0.0275 (10)	0.0249 (10)	−0.0054 (8)	0.0001 (8)	−0.0126 (9)
C8	0.0260 (11)	0.0363 (12)	0.0346 (11)	−0.0126 (9)	0.0048 (9)	−0.0168 (10)
C9	0.0311 (12)	0.0424 (13)	0.0433 (13)	−0.0167 (10)	−0.0003 (9)	−0.0223 (11)
C10	0.0303 (11)	0.0349 (12)	0.0317 (11)	−0.0123 (9)	0.0006 (9)	−0.0182 (10)
C11	0.0252 (10)	0.0225 (10)	0.0236 (10)	−0.0051 (8)	−0.0016 (8)	−0.0095 (8)

Ag1—N1	2.1092 (19)	C2—C3	1.342 (4)
Ag1—N3	2.110 (2)	C2—H2B	0.9300
Ag1—O1	2.8180 (19)	C3—H3A	0.9300
S1—O1	1.4451 (19)	C4—H4B	0.9300
S1—O3	1.4511 (16)	C5—C6	1.343 (4)
S1—O2	1.4573 (18)	C5—H5A	0.9300
S1—C7	1.787 (2)	C6—H6A	0.9300
N1—C1	1.318 (3)	C7—C8	1.367 (3)
N1—C3	1.371 (3)	C7—C11i	1.426 (3)
N2—C1	1.329 (3)	C8—C9	1.396 (3)
N2—C2	1.354 (4)	C8—H8A	0.9300
N2—H2A	0.8600	C9—C10	1.358 (3)
N3—C4	1.318 (3)	C9—H9A	0.9300
N3—C6	1.361 (4)	C10—C11	1.423 (3)
N4—C4	1.330 (4)	C10—H10A	0.9300
N4—C5	1.351 (4)	C11—C7i	1.426 (3)
N4—H4A	0.8600	C11—C11i	1.428 (4)
C1—H1A	0.9300
N1—Ag1—N3	176.72 (8)	C2—C3—N1	109.5 (2)
N1—Ag1—O1	89.09 (7)	C2—C3—H3A	125.2
N3—Ag1—O1	94.16 (7)	N1—C3—H3A	125.2
O1—S1—O3	113.46 (11)	N3—C4—N4	110.8 (3)
O1—S1—O2	113.10 (11)	N3—C4—H4B	124.6
O3—S1—O2	111.15 (10)	N4—C4—H4B	124.6
O1—S1—C7	105.46 (10)	C6—C5—N4	105.9 (3)
O3—S1—C7	107.98 (9)	C6—C5—H5A	127.0
O2—S1—C7	105.03 (10)	N4—C5—H5A	127.0
S1—O1—Ag1	128.71 (10)	C5—C6—N3	110.0 (3)
C1—N1—C3	105.4 (2)	C5—C6—H6A	125.0
C1—N1—Ag1	130.79 (18)	N3—C6—H6A	125.0
C3—N1—Ag1	123.79 (16)	C8—C7—C11i	120.85 (19)
C1—N2—C2	107.9 (2)	C8—C7—S1	117.59 (16)
C1—N2—H2A	126.1	C11i—C7—S1	121.48 (16)
C2—N2—H2A	126.1	C7—C8—C9	120.6 (2)
C4—N3—C6	105.3 (2)	C7—C8—H8A	119.7
C4—N3—Ag1	126.0 (2)	C9—C8—H8A	119.7
C6—N3—Ag1	128.55 (18)	C10—C9—C8	120.8 (2)
C4—N4—C5	108.0 (2)	C10—C9—H9A	119.6
C4—N4—H4A	126.0	C8—C9—H9A	119.6
C5—N4—H4A	126.0	C9—C10—C11	120.8 (2)
N1—C1—N2	110.9 (2)	C9—C10—H10A	119.6
N1—C1—H1A	124.5	C11—C10—H10A	119.6
N2—C1—H1A	124.5	C10—C11—C7i	123.01 (18)
C3—C2—N2	106.3 (2)	C10—C11—C11i	118.9 (2)
C3—C2—H2B	126.8	C7i—C11—C11i	118.1 (2)
N2—C2—H2B	126.8
O3—S1—O1—Ag1	−21.44 (16)	C5—N4—C4—N3	−0.2 (3)
O2—S1—O1—Ag1	106.34 (13)	C4—N4—C5—C6	0.2 (3)
C7—S1—O1—Ag1	−139.42 (11)	N4—C5—C6—N3	−0.1 (3)
N1—Ag1—O1—S1	−117.49 (14)	C4—N3—C6—C5	0.0 (3)
N3—Ag1—O1—S1	62.94 (14)	Ag1—N3—C6—C5	−175.65 (19)
O1—Ag1—N1—C1	165.5 (2)	O1—S1—C7—C8	−105.14 (19)
O1—Ag1—N1—C3	−11.9 (2)	O3—S1—C7—C8	133.26 (18)
O1—Ag1—N3—C4	−85.4 (2)	O2—S1—C7—C8	14.6 (2)
O1—Ag1—N3—C6	89.4 (2)	O1—S1—C7—C11i	71.72 (19)
C3—N1—C1—N2	0.1 (3)	O3—S1—C7—C11i	−49.88 (19)
Ag1—N1—C1—N2	−177.57 (16)	O2—S1—C7—C11i	−168.56 (16)
C2—N2—C1—N1	0.1 (3)	C11i—C7—C8—C9	0.9 (3)
C1—N2—C2—C3	−0.3 (3)	S1—C7—C8—C9	177.80 (18)
N2—C2—C3—N1	0.4 (3)	C7—C8—C9—C10	0.1 (4)
C1—N1—C3—C2	−0.3 (3)	C8—C9—C10—C11	−1.0 (4)
Ag1—N1—C3—C2	177.61 (18)	C9—C10—C11—C7i	−179.0 (2)
C6—N3—C4—N4	0.1 (3)	C9—C10—C11—C11i	0.9 (4)
Ag1—N3—C4—N4	175.93 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ii	0.86	1.96	2.786 (3)	161
N2—H2A···O3iii	0.86	2.37	2.998 (3)	130
N2—H2A···O3iv	0.86	2.32	3.082 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2i	0.86	1.96	2.786 (3)	161
N2—H2A⋯O3ii	0.86	2.37	2.998 (3)	130
N2—H2A⋯O3iii	0.86	2.32	3.082 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) .