Bis[bis(1H-imidazole-κN³)silver(I)] naphthalene-1,5-disulfonate

The title compound, [Ag(C₃H₄N₂)₂]₂(C₁₀H₆O₆S₂), exists in the form of isolated cations and anions with electrostatic inter­action between them. The Ag atom is two-coordinated by the N atoms of two crystallographically independent imidazole mol­ecules. The naphthalene-1,5-disulfonate anion is located on a crystallographic center of symmetry. The cations and anions are connected through inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.026
• wR factor = 0.063
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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S1. Comment

In the part of our recent investigations into the development of mixed inorganic–organic hybrid materials, we synthesized the silver sulfonate compound, which can be possess a potential wide chemical opportunity.

Sulfonate compounds have received much attention due to their potential application in chemical absorption and separation (Cai et al., 2004; Zhou et al., 2004; Liu et al., 2006). However, the weak coordination nature of SO₃–group makes its coordination mode very flexible and sensitive to the chemical environment (Côté et al., 2003). Likewise, Ag⁺ ion is a notoriously pliant with respect to its coordination sphere. Thus, in silver sulfonates, various coordination modes are observed with coordination number ranging from two to nine (Côté et al., 2004; Dalrymple et al., 2002; Reddy et al., 2003; Shimizu et al., 1999). On the other hand, the coordination behavior of arene–sulfonates with transition metals can be peculiar in the presence of amino ligands (Chen et al., 2001; Cai et al., 2001; Chen et al., 2002).

The structure of the title compound, (I), is depicted in Fig. 1. There is one crystallographically independent Ag centre, coordinated by two nitrogen atoms from two different imidazole ligands with Ag—N1 = 2.1088 (19)Å and Ag—N2 = 2.109 (2) Å, respectively. The lesser contact distance Ag···O1 = 2.8185 (19)Å is longer than the reported Ag···O distance (Lian et al., 2007).

Cations and anions are connected through intermolecular N—H···O hydrogen bonds to form a linear tapes (N4—H4A···O2ⁱⁱ): N4···O2ⁱⁱ = 2.786 (3) Å, H4A···O2ⁱⁱ = 1.96Å and angle N4—H4A···O2ⁱⁱ = 160.7°, which run along the a–axis. The linear tapes are arranged in parallel fashion and further linked via hydrogen bonding between the coordinated imidazole molecules and the sulfonate oxygen atoms, thus leading to neutral extended two–dimensional sheets (N2—H2A···O3ⁱⁱⁱ): N2···O3ⁱⁱⁱ = 2.998 (3) Å, angle N2—H2A···O3ⁱⁱⁱ = 129.8° and (N2—H2A···O3^iv): N2···O3^iv = 3.082 (3) Å, angle N2—H2A···O3^iv = 148.6° as shown on Fig. 2 (symmetry codes: (ii) 1 + x, y, z); (iii) x - 2, y + 1, z; (iv) -x, 2 - y, 2 - z).

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).

S2. Experimental

Disodium 1,5–naphthalene–disulfonate (0.33 g, 1 mmol) and imidazole (0.27 g, 4 mmol) were added to an aqueous solution of AgNO₃ (0.32 g, 2 mmol) (10 ml). The result solution was stirred at 343 K for four hours in a water bath. After filtration, a clear solution was set aside to crystallize.

S3. Refinement

All H atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å, N—H = 0.86 Å, respectively, and with U_iso(H) = 1.2U_eq(C or N)

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of I with the numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres with arbitrary radius. Symmetry code: (i) 1 - x, 1 - y, 1 - z.
	Fig. 2. View of the sheet structure of I normal to the ac–plane. Hydrogen bonds are represented as dashed lines.

Bis[bis(1H-imidazole-κN³)silver(I)] naphthalene-1,5-disulfonate

Crystal data

[Ag(C3H4N2)2](C10H6O6S2)	Z = 1
Mr = 774.36	F(000) = 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 = 2.2–27.5°
c = 10.2620 (13) Å	µ = 1.68 mm^−1
α = 65.286 (2)°	T = 293 K
β = 76.311 (2)°	Block, colourless
γ = 66.791 (2)°	0.50 × 0.30 × 0.13 mm
V = 665.89 (15) Å^3

Data collection

Bruker Smart 1000 CCD diffractometer	2962 independent reflections
Radiation source: Fine–focus sealed tube	2417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
ϕ– and ω–scans	θmax = 27.5°, θmin = 2.2°
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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0388P)^2] where P = (Fo^2 + 2Fc^2)/3
2962 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

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

Geometric parameters (Å, º)

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—C11^i	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—C7^i	1.426 (3)
N4—H4A	0.8600	C11—C11^i	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—C11^i	120.85 (19)
C1—N2—C2	107.9 (2)	C8—C7—S1	117.59 (16)
C1—N2—H2A	126.1	C11^i—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—C7^i	123.01 (18)
C3—C2—N2	106.3 (2)	C10—C11—C11^i	118.9 (2)
C3—C2—H2B	126.8	C7^i—C11—C11^i	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—C11^i	71.72 (19)
C3—N1—C1—N2	0.1 (3)	O3—S1—C7—C11^i	−49.88 (19)
Ag1—N1—C1—N2	−177.57 (16)	O2—S1—C7—C11^i	−168.56 (16)
C2—N2—C1—N1	0.1 (3)	C11^i—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—C7^i	−179.0 (2)
C6—N3—C4—N4	0.1 (3)	C9—C10—C11—C11^i	0.9 (4)
Ag1—N3—C4—N4	175.93 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2^ii	0.86	1.96	2.786 (3)	161
N2—H2A···O3^iii	0.86	2.37	2.998 (3)	130
N2—H2A···O3^iv	0.86	2.32	3.082 (3)	149

Symmetry codes: (ii) x+1, y, z; (iii) x−1, y+1, z; (iv) −x, −y+2, −z+2.