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Acta Cryst. (2007). E63, m1622-m1623    [ doi:10.1107/S1600536807021897 ]

catena-Poly[[(2-amino-3,5-dimethylbenzenesulfonato-[kappa]O)silver(I)]-[mu]-1,1'-(butane-1,4-diyl)diimidazole-[kappa]2N3:N3']

J.-J. Han and N. Li

Abstract top

In the title compound, [Ag(C8H10NO3S)(C10H14N4)], each AgI cation is three-coordinated by two N atoms from two different 1,1'-(butane-1,4-diyl)diimidazole ligands (bbi), and one sulfonate O atom from one 2-amino-3,5-dimethylbenzenesulfonate (L) anion in a distorted trigonal-planar geometry. Each bbi molecule acts as a bidentate ligand that binds two AgI atoms, thus forming a one-dimensional chain. The L anions are attached on both sides of the chain through Ag-O bonds. Finally, N-H...O hydrogen bonds link the chains together, reinforcing the crystal cohesion.

Comment top

Recently, intense interest has been focused on silver(I) sulfonates due to their interesting structures and properties (May & Shimizu, 2005). Based on previous reports, the structure motif of most silver(I) sulfonates observed is a two-dimensional layer, which is similar to that of metal phosphonates (Sun et al., 2004). So far, some silver(I) sulfonate compounds modified by nitrogen-based ligands that display different structure motifs depending upon the presence of secondary ligands have been reported (You et al., 2004). However, the information on silver sulfonate coordination polymers are not yet well understood, especially, investigations of silver(I) sulfonates with neutral ligands are rather insufficient. We selected 2-amino-3,5-dimethylbenzenesulfonic acid (HL) as a sulfonate ligand and 1,1'-(1,4-butanediyl)-bis(imidazole) (bbi) as a secondary ligand, generating a new chain coordination polymer, [Ag(L)(bbi)], (I), which is reported here.

In compound (I), each AgI cation is three-coordinated by two N atoms from two different bbi ligands, and one sulfonate O atom from one L anion in a distorted trigonal-planar geometry (Fig. 1, Table 1). As shown in Fig. 2, each bbi moiety acts as a bidentate ligand that binds two AgI atoms, thus forming a one-dimensional chain. The L anions are attached on both sides of the chain through the Ag—O bonds. Moreover, N—H···O hydrogen bonds (Table 2) link the chains together, reinforcing the crystal cohesion of (I).

Related literature top

The related compound, [Ag(L)(bipy)] (bipy = 2,2'-bipyridine), has a mononuclear structure in which the AgI cation is three-coordinated by two N atoms from one bipy molecule and one N atom from a L anion in a highly distorted trigonal-planar geometry. An intramolecular N—H···O hydrogen bond helps to establish the molecular conformation (Liu et al., 2006). For related literature, see: May & Shimizu (2005); Sun et al. (2004); You & Zhu (2004).

Experimental top

To a mixture of HL (0.5 mmol) and NaOH (0.5 mmol) in water was added AgNO3 (0.5 mmol) with constant stirring, to which was added bbi (0.5 mmol) in water. After the sample was stirred for 5 min, the precipitate was dissolved by dropwise addition of aqueous NH3 solution. Colorless crystals of (I) were obtained from the filtrate by slow evaporation after standing in the dark for three days (45% yield).

Refinement top

The H atoms bonded to N atom were located in a difference map and their positions were refined freely, with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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 top
[Figure 1] Fig. 1. The asymmetirc unit of (I), expanded to show the silver coordination. Displacement ellipsoids are drawn at the 30% probability level. (arbitrary spheres for the H atoms). Symmetry code: (i) x - 1, 1/2 - y, z - 1/2.
[Figure 2] Fig. 2. View of the chain structure in (I). H atoms have been omitted.
catena-Poly[[(2-amino-3,5-dimethylbenzenesulfonato-κO)silver(I)]- µ-1,1'-(butane-1,4-diyl)diimidazole-κ2N3:N3'] top
Crystal data top
[Ag(C8H10NO3S)(C10H14N4)]F(000) = 1016
Mr = 498.35Dx = 1.610 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13313 reflections
a = 8.6632 (17) Åθ = 3.3–27.5°
b = 17.239 (3) ŵ = 1.11 mm−1
c = 13.789 (3) ÅT = 292 K
β = 93.11 (3)°Block, colorless
V = 2056.3 (7) Å30.31 × 0.27 × 0.24 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4617 independent reflections
Radiation source: rotating anode2695 reflections with I > 2σ(I)
graphiteRint = 0.050
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.9°
ω scansh = −11→10
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −21→22
Tmin = 0.703, Tmax = 0.764l = −17→17
17540 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difmap and geom
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0495P)2]
where P = (Fo2 + 2Fc2)/3
4617 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.69 e Å−3
Crystal data top
[Ag(C8H10NO3S)(C10H14N4)]V = 2056.3 (7) Å3
Mr = 498.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.6632 (17) ŵ = 1.11 mm−1
b = 17.239 (3) ÅT = 292 K
c = 13.789 (3) Å0.31 × 0.27 × 0.24 mm
β = 93.11 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4617 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2695 reflections with I > 2σ(I)
Tmin = 0.703, Tmax = 0.764Rint = 0.050
17540 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100Δρmax = 0.71 e Å−3
S = 0.98Δρmin = −0.69 e Å−3
4617 reflectionsAbsolute structure: ?
263 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C10.9861 (4)0.11829 (16)−0.1790 (2)0.0349 (8)
C21.0868 (4)0.11463 (17)−0.0946 (2)0.0363 (8)
C31.2453 (4)0.12822 (18)−0.1037 (3)0.0403 (8)
C41.2984 (4)0.14376 (19)−0.1950 (3)0.0469 (9)
H41.40370.1519−0.20070.056*
C51.2009 (4)0.14763 (19)−0.2781 (3)0.0466 (9)
C61.0449 (4)0.13536 (17)−0.2681 (2)0.0426 (8)
H60.97740.1387−0.32270.051*
C71.2654 (6)0.1640 (3)−0.3765 (3)0.0840 (15)
H7A1.36220.1909−0.36730.126*
H7B1.19360.1956−0.41450.126*
H7C1.28130.1160−0.40970.126*
C81.3569 (4)0.1259 (2)−0.0155 (3)0.0624 (11)
H8A1.32780.16440.03040.094*
H8B1.45960.1364−0.03480.094*
H8C1.35400.07550.01390.094*
C9−0.1508 (4)0.0935 (2)0.4814 (3)0.0509 (9)
H9A−0.19690.06820.53190.061*
C10−0.0880 (4)0.0588 (2)0.4058 (3)0.0506 (10)
H10A−0.08330.00570.39460.061*
C11−0.0647 (4)0.18262 (19)0.3921 (3)0.0482 (9)
H11A−0.03940.23120.36820.058*
C120.6619 (4)0.0826 (2)0.1489 (3)0.0503 (10)
H120.69450.05140.09900.060*
C130.5835 (4)0.0580 (2)0.2255 (3)0.0498 (9)
H130.55210.00750.23740.060*
C140.6224 (4)0.1819 (2)0.2376 (3)0.0455 (9)
H140.62160.23240.26130.055*
C150.0521 (4)0.1066 (2)0.2605 (3)0.0557 (10)
H15A0.00060.13610.20830.067*
H15B0.05060.05240.24140.067*
C160.2177 (4)0.1334 (2)0.2742 (3)0.0597 (11)
H16A0.26740.12680.21330.072*
H16B0.21810.18840.28910.072*
C170.3117 (4)0.0917 (3)0.3527 (3)0.0606 (11)
H17A0.31810.03730.33550.073*
H17B0.25840.09510.41270.073*
C180.4740 (4)0.1231 (3)0.3706 (3)0.0646 (11)
H18A0.46900.17610.39390.078*
H18B0.52850.09230.42050.078*
N11.0317 (5)0.1013 (2)−0.0026 (2)0.0518 (8)
N2−0.0326 (3)0.11565 (15)0.3484 (2)0.0419 (7)
N3−0.1360 (3)0.17177 (17)0.4721 (2)0.0485 (8)
N40.6856 (3)0.16103 (17)0.1567 (2)0.0476 (7)
N50.5597 (3)0.12121 (17)0.2814 (2)0.0445 (7)
O10.7257 (3)0.16763 (13)−0.1191 (2)0.0567 (7)
O20.7185 (3)0.09931 (16)−0.2709 (2)0.0682 (8)
O30.7705 (3)0.02929 (13)−0.1206 (2)0.0617 (8)
S10.78366 (10)0.10201 (5)−0.17196 (7)0.0420 (2)
Ag10.78216 (4)0.23648 (2)0.05684 (3)0.07189 (16)
H1A0.945 (5)0.081 (2)−0.003 (3)0.052 (13)*
H1B1.101 (4)0.079 (2)0.041 (3)0.056 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.043 (2)0.0287 (16)0.033 (2)0.0022 (14)0.0029 (16)−0.0007 (13)
C20.044 (2)0.0316 (17)0.034 (2)0.0016 (14)0.0070 (16)−0.0006 (13)
C30.044 (2)0.0363 (18)0.040 (2)−0.0019 (15)−0.0024 (17)0.0019 (15)
C40.045 (2)0.041 (2)0.055 (3)−0.0021 (15)0.010 (2)0.0000 (16)
C50.060 (3)0.046 (2)0.035 (2)−0.0056 (17)0.0146 (19)−0.0003 (16)
C60.060 (2)0.0356 (18)0.032 (2)−0.0013 (16)0.0001 (17)0.0003 (14)
C70.097 (4)0.111 (4)0.047 (3)−0.029 (3)0.026 (3)0.003 (2)
C80.049 (2)0.080 (3)0.057 (3)−0.008 (2)−0.009 (2)0.012 (2)
C90.050 (2)0.060 (3)0.043 (2)0.0042 (18)0.0026 (18)0.0067 (18)
C100.055 (2)0.037 (2)0.059 (3)0.0012 (17)−0.001 (2)0.0004 (17)
C110.060 (2)0.0362 (19)0.049 (3)0.0074 (17)0.007 (2)−0.0004 (16)
C120.043 (2)0.058 (2)0.050 (3)−0.0057 (18)0.0050 (19)−0.0118 (18)
C130.046 (2)0.046 (2)0.058 (3)−0.0095 (17)0.0064 (19)0.0057 (18)
C140.039 (2)0.045 (2)0.052 (3)−0.0072 (16)−0.0029 (18)−0.0025 (17)
C150.047 (2)0.076 (3)0.043 (2)0.0123 (19)0.0011 (18)−0.0071 (19)
C160.055 (3)0.083 (3)0.041 (2)0.007 (2)0.014 (2)0.008 (2)
C170.048 (2)0.095 (3)0.041 (2)−0.002 (2)0.0167 (19)0.009 (2)
C180.046 (2)0.107 (3)0.041 (3)−0.012 (2)0.0067 (19)−0.002 (2)
N10.051 (2)0.070 (2)0.034 (2)−0.0012 (19)0.0039 (17)0.0069 (16)
N20.0392 (16)0.0452 (17)0.0414 (18)0.0083 (13)0.0012 (13)−0.0061 (13)
N30.0490 (19)0.054 (2)0.043 (2)0.0145 (14)0.0036 (15)−0.0046 (14)
N40.0407 (18)0.0587 (19)0.043 (2)−0.0107 (14)0.0018 (15)0.0050 (14)
N50.0377 (17)0.0597 (19)0.0362 (18)−0.0071 (14)0.0031 (13)−0.0034 (14)
O10.0463 (15)0.0505 (15)0.074 (2)0.0030 (11)0.0116 (14)−0.0132 (13)
O20.0563 (17)0.092 (2)0.0547 (19)−0.0096 (14)−0.0140 (14)−0.0007 (16)
O30.0518 (16)0.0430 (14)0.090 (2)−0.0092 (12)0.0051 (15)0.0192 (13)
S10.0400 (5)0.0395 (5)0.0460 (6)−0.0017 (4)−0.0010 (4)0.0007 (4)
Ag10.0656 (2)0.0907 (3)0.0585 (2)−0.03257 (18)−0.00434 (16)0.02951 (18)
Geometric parameters (Å, °) top
C1—C61.386 (4)C12—H120.9300
C1—C21.418 (5)C13—N51.357 (4)
C1—S11.784 (3)C13—H130.9300
C2—N11.399 (4)C14—N41.319 (4)
C2—C31.405 (5)C14—N51.337 (4)
C3—C41.389 (5)C14—H140.9300
C3—C81.513 (5)C15—N21.460 (4)
C4—C51.388 (5)C15—C161.509 (5)
C4—H40.9300C15—H15A0.9700
C5—C61.382 (5)C15—H15B0.9700
C5—C71.522 (5)C16—C171.502 (6)
C6—H60.9300C16—H16A0.9700
C7—H7A0.9600C16—H16B0.9700
C7—H7B0.9600C17—C181.515 (5)
C7—H7C0.9600C17—H17A0.9700
C8—H8A0.9600C17—H17B0.9700
C8—H8B0.9600C18—N51.472 (4)
C8—H8C0.9600C18—H18A0.9700
C9—C101.343 (5)C18—H18B0.9700
C9—N31.362 (4)N1—H1A0.83 (4)
C9—H9A0.9300N1—H1B0.92 (4)
C10—N21.363 (4)O1—S11.450 (2)
C10—H10A0.9300O2—S11.448 (3)
C11—N31.307 (4)O3—S11.447 (2)
C11—N21.338 (4)Ag1—N42.101 (3)
C11—H11A0.9300Ag1—N3i2.112 (3)
C12—C131.354 (5)Ag1—O12.721 (3)
C12—N41.370 (4)
C6—C1—C2119.9 (3)N2—C15—C16112.3 (3)
C6—C1—S1119.4 (3)N2—C15—H15A109.1
C2—C1—S1120.7 (2)C16—C15—H15A109.1
N1—C2—C3119.5 (3)N2—C15—H15B109.1
N1—C2—C1121.8 (3)C16—C15—H15B109.1
C3—C2—C1118.6 (3)H15A—C15—H15B107.9
C4—C3—C2119.1 (3)C17—C16—C15114.7 (3)
C4—C3—C8120.3 (3)C17—C16—H16A108.6
C2—C3—C8120.5 (3)C15—C16—H16A108.6
C5—C4—C3122.7 (3)C17—C16—H16B108.6
C5—C4—H4118.6C15—C16—H16B108.6
C3—C4—H4118.6H16A—C16—H16B107.6
C6—C5—C4117.7 (3)C16—C17—C18114.1 (3)
C6—C5—C7121.8 (4)C16—C17—H17A108.7
C4—C5—C7120.5 (4)C18—C17—H17A108.7
C5—C6—C1122.0 (3)C16—C17—H17B108.7
C5—C6—H6119.0C18—C17—H17B108.7
C1—C6—H6119.0H17A—C17—H17B107.6
C5—C7—H7A109.5N5—C18—C17111.2 (3)
C5—C7—H7B109.5N5—C18—H18A109.4
H7A—C7—H7B109.5C17—C18—H18A109.4
C5—C7—H7C109.5N5—C18—H18B109.4
H7A—C7—H7C109.5C17—C18—H18B109.4
H7B—C7—H7C109.5H18A—C18—H18B108.0
C3—C8—H8A109.5C2—N1—H1A115 (3)
C3—C8—H8B109.5C2—N1—H1B115 (2)
H8A—C8—H8B109.5H1A—N1—H1B113 (4)
C3—C8—H8C109.5C11—N2—C10105.7 (3)
H8A—C8—H8C109.5C11—N2—C15126.3 (3)
H8B—C8—H8C109.5C10—N2—C15127.9 (3)
C10—C9—N3109.0 (3)C11—N3—C9105.8 (3)
C10—C9—H9A125.5C11—N3—Ag1ii123.2 (2)
N3—C9—H9A125.5C9—N3—Ag1ii130.8 (3)
C9—C10—N2107.5 (3)C14—N4—C12105.5 (3)
C9—C10—H10A126.3C14—N4—Ag1125.7 (2)
N2—C10—H10A126.3C12—N4—Ag1128.5 (3)
N3—C11—N2112.1 (3)C14—N5—C13107.1 (3)
N3—C11—H11A124.0C14—N5—C18126.5 (3)
N2—C11—H11A124.0C13—N5—C18126.3 (3)
C13—C12—N4109.1 (3)O3—S1—O2113.33 (17)
C13—C12—H12125.4O3—S1—O1113.01 (17)
N4—C12—H12125.4O2—S1—O1111.77 (17)
C12—C13—N5106.8 (3)O3—S1—C1105.46 (15)
C12—C13—H13126.6O2—S1—C1106.71 (16)
N5—C13—H13126.6O1—S1—C1105.84 (14)
N4—C14—N5111.5 (3)N4—Ag1—O1104.81 (10)
N4—C14—H14124.3O1—Ag1—N3i83.28 (10)
N5—C14—H14124.3N4—Ag1—N3i169.75 (12)
C6—C1—C2—N1176.8 (3)C16—C15—N2—C1164.0 (5)
S1—C1—C2—N1−2.6 (4)C16—C15—N2—C10−112.3 (4)
C6—C1—C2—C3−0.3 (4)N2—C11—N3—C90.2 (4)
S1—C1—C2—C3−179.7 (2)N2—C11—N3—Ag1ii−176.2 (2)
N1—C2—C3—C4−178.0 (3)C10—C9—N3—C11−0.2 (4)
C1—C2—C3—C4−0.8 (4)C10—C9—N3—Ag1ii175.7 (3)
N1—C2—C3—C82.0 (5)N5—C14—N4—C12−0.2 (4)
C1—C2—C3—C8179.2 (3)N5—C14—N4—Ag1174.7 (2)
C2—C3—C4—C51.0 (5)C13—C12—N4—C140.4 (4)
C8—C3—C4—C5−179.1 (3)C13—C12—N4—Ag1−174.2 (3)
C3—C4—C5—C60.0 (5)N4—C14—N5—C13−0.1 (4)
C3—C4—C5—C7−179.4 (3)N4—C14—N5—C18−177.3 (3)
C4—C5—C6—C1−1.2 (5)C12—C13—N5—C140.4 (4)
C7—C5—C6—C1178.2 (3)C12—C13—N5—C18177.6 (3)
C2—C1—C6—C51.3 (5)C17—C18—N5—C14121.1 (4)
S1—C1—C6—C5−179.2 (2)C17—C18—N5—C13−55.5 (5)
N3—C9—C10—N20.2 (4)C6—C1—S1—O3129.0 (3)
N4—C12—C13—N5−0.5 (4)C2—C1—S1—O3−51.5 (3)
N2—C15—C16—C1759.2 (5)C6—C1—S1—O28.2 (3)
C15—C16—C17—C18−175.8 (3)C2—C1—S1—O2−172.3 (2)
C16—C17—C18—N5−57.1 (5)C6—C1—S1—O1−111.0 (3)
N3—C11—N2—C100.0 (4)C2—C1—S1—O168.5 (3)
N3—C11—N2—C15−177.0 (3)C14—N4—Ag1—N3i−5.9 (8)
C9—C10—N2—C11−0.1 (4)C12—N4—Ag1—N3i167.8 (6)
C9—C10—N2—C15176.8 (3)
Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.83 (4)2.34 (4)2.985 (5)136 (3)
N1—H1B···O3iii0.92 (4)2.40 (4)3.252 (4)154 (3)
Symmetry codes: (iii) −x+2, −y, −z.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N42.101 (3)Ag1—O12.721 (3)
Ag1—N3i2.112 (3)
N4—Ag1—O1104.81 (10)N4—Ag1—N3i169.75 (12)
O1—Ag1—N3i83.28 (10)
Symmetry codes: (i) x+1, −y+1/2, z−1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.83 (4)2.34 (4)2.985 (5)136 (3)
N1—H1B···O3ii0.92 (4)2.40 (4)3.252 (4)154 (3)
Symmetry codes: (ii) −x+2, −y, −z.
Acknowledgements top

The authors thank Harbin Institute of Technology for supporting this work.

references
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