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Acta Cryst. (2007). E63, m3035    [ doi:10.1107/S1600536807049550 ]

catena-Poly[[(6-aminonaphthalene-1-sulfonato-[kappa]O)silver(I)]-[mu]-2,3,5,6-tetramethylpyrazine-[kappa]2N:N']

H.-Y. Liu, J.-C. Ma and Y.-Y. Liu

Abstract top

In the title compound, [Ag(C10H8NO3S)(C8H12N2)]n, the Ag+ cation is three-coordinated by two N atoms from two 2,3,5,6-tetramethylpyrazine ligands and one O atom from a 7-aminonaphthalene-1-sulfonate anion. The 2,3,5,6-tetramethylpyrazine ligand acts as a bridging bidentate ligand, linking the AgI centres into a one-dimensional chain. The chains are interconnected via intermolecular N-H...O hydrogen bonds and C-H...[pi] interactions, resulting in the formation of a three-dimensional framework.

Comment top

As part of an investigation of the transition metal application there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound is described.

As shown in Fig. 1, the AgI ion is three coordinated by two N atoms from two 2,3,5,6-tetramethylpyrazine ligands and one O atom from a 7-aminonaphthalene-1-sulfonate anion. Each 2,3,5,6-tetramethylpyrazine ligand coordinates to two AgI cations through its two aromatic N atoms, thus acing as a bridging bidentate ligand. The AgI cations are bridged by 2,3,5,6-tetramethylpyrazine ligands to a chain structure. In the chain, face-to-face π–π interaction is observed between the naphthalene ring system and the adjacent pyrazine ring, with a ring centroid-to-centriod distance of 3.517 (1) Å. (Fig. 2). Intermolecular N—H···O hydrogen bonds (Table 2) involving the amino N atom and two sulfonate O atoms of two adjacent 7-aminonaphthalene-1-sulfonate anions link the chains into a three-dimensional framework (Fig. 3). A C—H···π interaction (Table 2) between a methyl group of the 2,3,5,6-tetramethylpyrazine ligand and the C1–C4/C10/C9 benzene ring (centroid Cg1) of the adjacent naphthalene ring system further stabilize the three-dimensional framework.

Related literature top

The bond distances and angles in the title compound are normal (Wu et al., 2006).

Experimental top

An aqueous solution (10 ml) of 7-aminonaphthalene-1-sulfonic 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. 2,3,5,6-tetramethylpyrazine (0.068 g, 0.5 mmol) in methanol (5 ml) was then added and a white precipitate formed. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M), and crystals of the title compound were obtained by slow evaporation of the solvent for several days at room temperature.

Refinement top

H atoms of the amino group were located in a difference map and refined isotropically with Uiso = 1.5Ueq(N). C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso = 1.2Ueq (C) for aromatic H atoms and C—H = 0.96 Å and Uiso = 1.5Ueq (C) for methyl H atoms. The maximum residual density peak is 0.71 Å from atom Ag1.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the local coordination of the AgI cation in the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Part of the polymeric chain in the title compound, showing face-to-face π–π interactions as dashed lines.
[Figure 3] Fig. 3. Part of the crystal structure of the title compound, showing N—H···O hydrogen bonds (dashed lines). C-bound H-atoms have been omitted for clarity.
catena-Poly[[(6-aminonaphthalene-1-sulfonato-kO)silver(I)]-µ-2,3,5,6- tetramethylpyrazine-κ2N:N'] top
Crystal data top
[Ag(C10H8NO3S)(C8H12N2)]F000 = 944
Mr = 466.30Dx = 1.833 Mg m−3
Monoclinic, CcMo Kα radiation
λ = 0.71069 Å
Hall symbol: C -2ycCell parameters from 8199 reflections
a = 10.101 (5) Åθ = 3.2–27.5º
b = 10.631 (6) ŵ = 1.34 mm−1
c = 15.831 (7) ÅT = 293 (2) K
β = 96.180 (19)ºBlock, yellow
V = 1690.1 (15) Å30.21 × 0.16 × 0.15 mm
Z = 4
Data collection top
Bruker APEX CCD area-detector
diffractometer		3626 independent reflections
Radiation source: fine-focus sealed tube3534 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 293(2) Kθmax = 27.5º
ω scansθmin = 3.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→13
Tmin = 0.765, Tmax = 0.808k = −13→13
8210 measured reflectionsl = −20→20
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.020  w = 1/[σ2(Fo2) + (0.0278P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.047(Δ/σ)max = 0.002
S = 1.12Δρmax = 0.51 e Å−3
3626 reflectionsΔρmin = −0.19 e Å−3
245 parametersExtinction correction: none
4 restraintsAbsolute structure: Flack (1983), with 1687 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.001 (14)
Secondary atom site location: difference Fourier map
Crystal data top
[Ag(C10H8NO3S)(C8H12N2)]V = 1690.1 (15) Å3
Mr = 466.30Z = 4
Monoclinic, CcMo Kα
a = 10.101 (5) ŵ = 1.34 mm−1
b = 10.631 (6) ÅT = 293 (2) K
c = 15.831 (7) Å0.21 × 0.16 × 0.15 mm
β = 96.180 (19)º
Data collection top
Bruker APEX CCD area-detector
diffractometer		3626 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3534 reflections with I > 2σ(I)
Tmin = 0.765, Tmax = 0.808Rint = 0.016
8210 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.020H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.047Δρmax = 0.51 e Å−3
S = 1.12Δρmin = −0.19 e Å−3
3626 reflectionsAbsolute structure: Flack (1983), with 1687 Friedel pairs
245 parametersFlack parameter: −0.001 (14)
4 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
Ag10.404494 (13)0.904978 (15)0.914016 (11)0.03466 (6)
C10.4695 (2)0.61273 (18)0.79933 (12)0.0199 (4)
C20.3599 (2)0.5415 (2)0.77423 (14)0.0275 (4)
H20.31260.55530.72140.033*
C30.3183 (2)0.4473 (2)0.82799 (17)0.0334 (5)
H30.24280.39980.81090.040*
C40.3888 (3)0.4256 (2)0.9052 (2)0.0306 (5)
H40.36000.36330.94030.037*
C50.5778 (2)0.4698 (2)1.01204 (13)0.0252 (4)
H50.55020.40541.04580.030*
C60.6894 (2)0.5382 (2)1.03999 (13)0.0246 (4)
C70.7290 (3)0.6356 (3)0.98737 (15)0.0304 (5)
H70.80410.68281.00580.037*
C80.6608 (2)0.6625 (2)0.91078 (14)0.0282 (4)
H80.68990.72740.87800.034*
C90.5449 (2)0.59244 (18)0.87993 (14)0.0214 (4)
C100.5043 (2)0.49545 (19)0.93312 (13)0.0228 (4)
C110.2410 (2)0.6798 (2)0.98876 (14)0.0240 (4)
C120.1527 (2)0.73938 (19)0.85327 (13)0.0237 (4)
C130.5543 (2)1.1474 (2)0.85442 (14)0.0215 (4)
C140.6417 (2)1.0872 (2)0.98955 (14)0.0246 (4)
C150.3439 (2)0.6982 (2)1.06260 (15)0.0329 (5)
H15A0.40580.76181.04910.049*
H15B0.39060.62061.07500.049*
H15C0.30160.72411.11120.049*
C160.1599 (2)0.8227 (2)0.77814 (14)0.0317 (5)
H16A0.21670.89310.79400.047*
H16B0.07230.85250.75840.047*
H16C0.19520.77630.73370.047*
C170.4499 (2)1.1309 (2)0.78121 (16)0.0318 (5)
H17A0.38241.07470.79700.048*
H17B0.48951.09640.73380.048*
H17C0.41071.21100.76570.048*
C180.6354 (3)1.0027 (3)1.06474 (16)0.0399 (6)
H18A0.55560.95321.05690.060*
H18B0.63521.05271.11520.060*
H18C0.71150.94801.07020.060*
N10.24569 (17)0.75411 (17)0.92050 (11)0.0233 (3)
N20.55020 (18)1.07168 (17)0.92248 (11)0.0234 (4)
N30.7676 (2)0.5116 (2)1.11496 (13)0.0350 (5)
H2N0.821 (3)0.565 (3)1.136 (2)0.052*
H1N0.730 (3)0.463 (3)1.147 (2)0.052*
O10.50658 (17)0.84893 (15)0.77532 (10)0.0309 (3)
O20.41660 (17)0.72625 (17)0.65422 (10)0.0353 (4)
O30.64820 (15)0.70373 (17)0.70974 (10)0.0313 (3)
S10.51364 (5)0.73176 (5)0.72854 (3)0.02202 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.03143 (8)0.03442 (9)0.03796 (9)−0.01554 (8)0.00295 (6)−0.00011 (8)
C10.0198 (9)0.0185 (9)0.0214 (9)0.0009 (7)0.0016 (8)−0.0010 (7)
C20.0232 (10)0.0249 (10)0.0330 (11)−0.0013 (8)−0.0042 (9)−0.0052 (9)
C30.0262 (11)0.0250 (11)0.0478 (14)−0.0111 (9)−0.0021 (10)−0.0014 (10)
C40.0301 (14)0.0223 (9)0.0398 (14)−0.0104 (10)0.0061 (11)0.0013 (10)
C50.0314 (11)0.0207 (10)0.0244 (9)−0.0020 (8)0.0071 (8)0.0031 (7)
C60.0300 (10)0.0219 (10)0.0216 (9)0.0035 (8)0.0011 (8)−0.0011 (8)
C70.0295 (12)0.0336 (13)0.0270 (11)−0.0130 (10)−0.0023 (10)0.0027 (10)
C80.0281 (10)0.0273 (11)0.0283 (9)−0.0126 (8)−0.0012 (9)0.0046 (8)
C90.0208 (9)0.0212 (10)0.0221 (9)−0.0024 (7)0.0020 (8)−0.0026 (7)
C100.0238 (9)0.0193 (9)0.0257 (10)−0.0024 (8)0.0041 (8)−0.0036 (7)
C110.0220 (9)0.0244 (10)0.0257 (9)0.0004 (8)0.0028 (8)−0.0073 (8)
C120.0216 (9)0.0229 (10)0.0268 (9)0.0027 (8)0.0037 (8)−0.0020 (8)
C130.0178 (9)0.0199 (11)0.0266 (10)0.0020 (8)0.0010 (8)−0.0038 (8)
C140.0235 (10)0.0265 (11)0.0240 (10)−0.0016 (8)0.0035 (9)−0.0015 (8)
C150.0268 (11)0.0403 (14)0.0302 (11)−0.0030 (10)−0.0027 (9)−0.0074 (10)
C160.0333 (11)0.0292 (11)0.0327 (11)−0.0004 (9)0.0044 (9)0.0052 (9)
C170.0321 (11)0.0260 (11)0.0344 (11)−0.0022 (9)−0.0100 (10)0.0000 (9)
C180.0465 (14)0.0428 (14)0.0293 (11)−0.0143 (11)−0.0007 (11)0.0057 (10)
N10.0200 (8)0.0235 (9)0.0269 (8)−0.0029 (6)0.0051 (7)−0.0063 (6)
N20.0212 (8)0.0243 (9)0.0246 (9)−0.0014 (7)0.0014 (7)−0.0041 (6)
N30.0430 (12)0.0343 (11)0.0254 (9)−0.0045 (9)−0.0062 (9)0.0040 (8)
O10.0371 (8)0.0217 (8)0.0348 (8)−0.0009 (6)0.0079 (7)−0.0007 (6)
O20.0335 (8)0.0437 (10)0.0263 (7)0.0006 (7)−0.0075 (7)0.0048 (7)
O30.0247 (7)0.0401 (9)0.0300 (8)0.0036 (7)0.0072 (6)0.0015 (6)
S10.0213 (2)0.0240 (2)0.0205 (2)0.00127 (18)0.00097 (19)0.00122 (18)
Geometric parameters (Å, °) top
Ag1—N12.279 (2)C12—C13i1.395 (3)
Ag1—N22.298 (2)C12—C161.491 (3)
Ag1—O12.5936 (19)C13—N21.349 (3)
C1—C21.364 (3)C13—C12ii1.395 (3)
C1—C91.430 (3)C13—C171.491 (3)
C1—S11.779 (2)C14—N21.341 (3)
C2—C31.408 (3)C14—C11ii1.406 (3)
C2—H20.93C14—C181.498 (3)
C3—C41.367 (4)C15—H15A0.96
C3—H30.93C15—H15B0.96
C4—C101.414 (3)C15—H15C0.96
C4—H40.93C16—H16A0.96
C5—C61.373 (3)C16—H16B0.96
C5—C101.409 (3)C16—H16C0.96
C5—H50.93C17—H17A0.96
C6—N31.383 (3)C17—H17B0.96
C6—C71.414 (3)C17—H17C0.96
C7—C81.359 (3)C18—H18A0.96
C7—H70.93C18—H18B0.96
C8—C91.428 (3)C18—H18C0.96
C8—H80.93N3—H2N0.83 (2)
C9—C101.419 (3)N3—H1N0.85 (2)
C11—N11.343 (3)O1—S11.4549 (18)
C11—C14i1.406 (3)O2—S11.4492 (17)
C11—C151.491 (3)O3—S11.4532 (17)
C12—N11.351 (3)
N1—Ag1—N2171.76 (6)N2—C14—C18118.1 (2)
N1—Ag1—O1102.85 (6)C11ii—C14—C18121.2 (2)
N2—Ag1—O185.19 (6)C11—C15—H15A109.5
C2—C1—C9120.92 (19)C11—C15—H15B109.5
C2—C1—S1117.51 (16)H15A—C15—H15B109.5
C9—C1—S1121.58 (15)C11—C15—H15C109.5
C1—C2—C3120.3 (2)H15A—C15—H15C109.5
C1—C2—H2119.9H15B—C15—H15C109.5
C3—C2—H2119.9C12—C16—H16A109.5
C4—C3—C2120.0 (2)C12—C16—H16B109.5
C4—C3—H3120.0H16A—C16—H16B109.5
C2—C3—H3120.0C12—C16—H16C109.5
C3—C4—C10121.6 (2)H16A—C16—H16C109.5
C3—C4—H4119.2H16B—C16—H16C109.5
C10—C4—H4119.2C13—C17—H17A109.5
C6—C5—C10121.25 (19)C13—C17—H17B109.5
C6—C5—H5119.4H17A—C17—H17B109.5
C10—C5—H5119.4C13—C17—H17C109.5
C5—C6—N3122.8 (2)H17A—C17—H17C109.5
C5—C6—C7118.17 (19)H17B—C17—H17C109.5
N3—C6—C7118.9 (2)C14—C18—H18A109.5
C8—C7—C6122.1 (2)C14—C18—H18B109.5
C8—C7—H7118.9H18A—C18—H18B109.5
C6—C7—H7118.9C14—C18—H18C109.5
C7—C8—C9120.9 (2)H18A—C18—H18C109.5
C7—C8—H8119.6H18B—C18—H18C109.5
C9—C8—H8119.6C11—N1—C12118.93 (19)
C10—C9—C8117.01 (19)C11—N1—Ag1122.42 (14)
C10—C9—C1118.60 (18)C12—N1—Ag1118.65 (15)
C8—C9—C1124.4 (2)C14—N2—C13118.76 (19)
C5—C10—C4120.9 (2)C14—N2—Ag1121.57 (14)
C5—C10—C9120.55 (18)C13—N2—Ag1119.22 (14)
C4—C10—C9118.5 (2)C6—N3—H2N120 (3)
N1—C11—C14i120.39 (19)C6—N3—H1N113 (2)
N1—C11—C15118.1 (2)H2N—N3—H1N119 (4)
C14i—C11—C15121.5 (2)S1—O1—Ag1132.33 (10)
N1—C12—C13i120.4 (2)O2—S1—O3113.03 (10)
N1—C12—C16118.0 (2)O2—S1—O1112.46 (10)
C13i—C12—C16121.5 (2)O3—S1—O1112.21 (11)
N2—C13—C12ii120.78 (19)O2—S1—C1106.81 (10)
N2—C13—C17118.1 (2)O3—S1—C1106.66 (10)
C12ii—C13—C17121.1 (2)O1—S1—C1105.01 (10)
N2—C14—C11ii120.7 (2)
C9—C1—C2—C30.7 (3)C13i—C12—N1—C11−0.8 (3)
S1—C1—C2—C3−178.85 (18)C16—C12—N1—C11−179.95 (19)
C1—C2—C3—C4−0.9 (4)C13i—C12—N1—Ag1179.48 (15)
C2—C3—C4—C10−0.3 (4)C16—C12—N1—Ag10.3 (2)
C10—C5—C6—N3−176.6 (2)O1—Ag1—N1—C11125.56 (16)
C10—C5—C6—C70.0 (3)O1—Ag1—N1—C12−54.73 (16)
C5—C6—C7—C8−0.3 (4)C11ii—C14—N2—C13−0.6 (3)
N3—C6—C7—C8176.5 (2)C18—C14—N2—C13179.8 (2)
C6—C7—C8—C90.0 (4)C11ii—C14—N2—Ag1171.63 (15)
C7—C8—C9—C100.7 (4)C18—C14—N2—Ag1−8.0 (3)
C7—C8—C9—C1−178.5 (2)C12ii—C13—N2—C140.6 (3)
C2—C1—C9—C100.7 (3)C17—C13—N2—C14−178.6 (2)
S1—C1—C9—C10−179.75 (15)C12ii—C13—N2—Ag1−171.77 (15)
C2—C1—C9—C8179.8 (2)C17—C13—N2—Ag19.0 (3)
S1—C1—C9—C8−0.6 (3)O1—Ag1—N2—C14−121.18 (17)
C6—C5—C10—C4−179.3 (2)O1—Ag1—N2—C1350.99 (16)
C6—C5—C10—C90.6 (3)N1—Ag1—O1—S1−24.43 (14)
C3—C4—C10—C5−178.4 (2)N2—Ag1—O1—S1157.43 (14)
C3—C4—C10—C91.7 (4)Ag1—O1—S1—O2102.13 (14)
C8—C9—C10—C5−0.9 (3)Ag1—O1—S1—O3−129.12 (12)
C1—C9—C10—C5178.25 (19)Ag1—O1—S1—C1−13.64 (15)
C8—C9—C10—C4179.0 (2)C2—C1—S1—O2−0.2 (2)
C1—C9—C10—C4−1.9 (3)C9—C1—S1—O2−179.73 (17)
C14i—C11—N1—C120.9 (3)C2—C1—S1—O3−121.29 (18)
C15—C11—N1—C12−179.54 (19)C9—C1—S1—O359.14 (19)
C14i—C11—N1—Ag1−179.44 (15)C2—C1—S1—O1119.45 (18)
C15—C11—N1—Ag10.2 (3)C9—C1—S1—O1−60.11 (19)
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H1N···O3iii0.85 (2)2.23 (3)3.055 (3)165 (4)
N3—H2N···O2iv0.83 (2)2.43 (3)3.197 (3)155 (3)
C16—H16B···Cg1v0.962.653.425 (3)138
Symmetry codes: (iii) x, −y+1, z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) x−1/2, y+1/2, z.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N12.279 (2)Ag1—O12.5936 (19)
Ag1—N22.298 (2)
N1—Ag1—N2171.76 (6)N2—Ag1—O185.19 (6)
N1—Ag1—O1102.85 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H1N···O3i0.85 (2)2.23 (3)3.055 (3)165 (4)
N3—H2N···O2ii0.83 (2)2.43 (3)3.197 (3)155 (3)
C16—H16B···Cg1iii0.962.653.425 (3)138
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) x−1/2, y+1/2, z.
Acknowledgements top

The authors thank the Analysis and Testing Foundation of Northeast Normal University for support.

references
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