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Acta Cryst. (2009). E65, m1042-m1043    [ doi:10.1107/S1600536809030268 ]

Bis[[mu]-1,2-bis(1H-imidazol-1-ylmethyl)benzene-[kappa]2N3:N3']disilver(I) 3-carboxylato-4-hydroxybenzenesulfonate methanol solvate trihydrate

H.-M. Sun, Y.-C. Chi and H.-Y. Liu

Abstract top

In the title compound, [Ag2(C14H14N4)2](C7H4O6S)·CH3OH·3H2O, the complex dication has a binuclear structure in which each AgI ion is two-coordinated in a slightly distorted linear coordination geometry. The two AgI atoms are bridged by two 1,2-bis[(1H-imidazol-1-yl)methyl]benzene (IBI) ligands, forming a 22-membered ring. In the dication, [pi]-[pi] interactions are observed between the imidazole rings with centroid-centroid distances of 3.472 (3) and 3.636 (3) Å. In the crystal, the uncoordinated water molecules, anions and methanol solvent molecules are linked into chains along the b axis by O-H...O hydrogen bonds. In addition, [pi]-[pi] interactions are observed between the benzene rings of the IBI ligands, with a centroid-centroid distance of 3.776 (2) Å. The sulfonate group is disordered over two orientations with occupancies of 0.676 (12) and 0.324 (12).

Comment top

The design and synthesis of silver(I) sulfonates have attracted intense interests of chemists (Cote & Shimizu, 2003; Ma et al., 2005). Some silver(I) sulfonate compounds, modified by secondary nitrogen-based ligands, have been reported (Cote & Shimizu, 2004; Liu et al., 2007). In most of these silver(I) sulfonate complexes, the sulfonate ligand acts as a counter-anion. Herein, we present a new silver-sulfonate complex (I), namely, [Ag2(IBI)2]L.CH3OH.3H2O, where IBI is 1,2-bis[(1H-imidazol-1-yl)methyl]benzene and L is 3-carboxy-4-hydroxybenzenesulfonic acid.

Selected bond distances and angles are listed in Table 1. The contents of the asymmetric unit is shown in Fig.1. The silver complex shows a binuclear structure, where each of AgI atom has a slightly distorted linear geometry and is coordinated by two N atoms from the IBI ligands. The Ag—N bond distances are within the normal range and are comparable to those observed in N-containing AgIcompounds (Li et al., 2006). Notably, the L ligand does not coordinate to the AgI center and acts as a counter-anion. In the complex dication, π–π interactions are observed between the imidazole rings with Cg1···Cg2 and Cg3···Cg4 distances of 3.472 (3) and 3.636 (3) Å, respectively; Cg1, Cg2, Cg3 and Cg4 are centroids of the N1/C16/C24/N4/C35, N2/C17/N3/C19/C18, N5/C20/N6/C22/C21 and N7/C32/C31/N8/C33, rings, respectively.

In the crystal, the lattice water molecules, sulfonate oxygen atoms, and hydroxyl oxygen atoms are involved in the formation of O—H···O hydrogen-bonded chains along the b axis (Table 2). In addition, π-π interactions between the benzene rings of the IBI ligands, with a Cg5···Cg6iii distance of 3.776 (2) Å [Cg5 and Cg6 are centroids of the C8-C13 and C24-C29 rings, respectively; symmetry code: (iii) x, y, 1+z] are observed (Fig.2).

Related literature top

For he design and synthesis of silver(I) sulfonates, see: Cote & Shimizu (2003); Ma et al. (2005). For silver(I) sulfonate compounds modified by secondary nitrogen-based ligands, see: Cote & Shimizu (2004); Liu et al. (2007). For Ag—N bond distances in N-containing AgIcompounds, see: Li et al. (2006).

Experimental top

An aqueous solution (10 ml) of 3-carboxy-4-hydroxybenzenesulfonate anion (1 mmol) was added to solid Ag2CO3 (0.5 mmol) and stirred for several minutes until no further CO2 was given off. 1-(3-(1H-Imidazol-1-yl)methyl)benzyl)-1H-imidazole (1 mmol) was then added and a precipitate was formed. The precipitate was dissolved by ammonium hydroxide. Single crystals of the title compound were obtained by slow evaporation of the solution for 5 d at room temperature.

Refinement top

Hydroxy H atoms were located in a difference map and refined with a O—H distance restraint of 0.85 (1) Å. Water H atoms were located in a difference Fourier map and refined with O—H and H···H distance restraints of 0.85 (1) Å and 1.35 (1) Å, respectively, and with Uiso(H) = 1.5Ueq(O). At this stage, short H···H contacts involving water H atoms were observed but attempts to locate alternate positions for these H atoms failed. Hence, the H1A···H3B, H1B···H3B, H1A···H2Bii and H3A···H3Aiii [symmetry code: (ii) -x,-y,1 - z); (iii): -x,1 - y,1 - z] distances were restrained to 2.20 (1) Å to avoid short H···H contacts. H atoms bonded to C atoms were positioned geometrically (C-H = 0.93 or 0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C). The sulfonate O atoms are disordered over two orientations with occupancies of 0.676 (12) and 0.324 (12).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The aymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the major disorder component of the C7H4O6S2- ion is shown.
[Figure 2] Fig. 2. View of the formation of a chain through π-π interactions in the title compound. The anions, methanol and water molecules have been omitted for clarity.
Bis[µ-1,2-bis(1H-imidazol-1-ylmethyl)benzene- κ2N3:N3']disilver(I) 3-carboxylato-4-hydroxybenzenesulfonate methanol solvate trihydrate top
Crystal data top
[Ag2(C14H14N4)2](C7H4O6S)·CH4O·3H2OZ = 2
Mr = 994.58F(000) = 1008
Triclinic, P1Dx = 1.688 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9959 (18) ÅCell parameters from 8696 reflections
b = 13.947 (3) Åθ = 3.0–27.5°
c = 16.008 (3) ŵ = 1.12 mm−1
α = 102.71 (3)°T = 293 K
β = 92.37 (3)°Block, colourless
γ = 91.34 (3)°0.18 × 0.15 × 0.12 mm
V = 1956.5 (7) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		8696 independent reflections
Radiation source: fine-focus sealed tube5684 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = −11→10
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −18→18
Tmin = 0.771, Tmax = 0.869l = −20→20
19149 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.9392P]
where P = (Fo2 + 2Fc2)/3
8696 reflections(Δ/σ)max = 0.001
569 parametersΔρmax = 0.48 e Å−3
15 restraintsΔρmin = −0.41 e Å−3
Crystal data top
[Ag2(C14H14N4)2](C7H4O6S)·CH4O·3H2Oγ = 91.34 (3)°
Mr = 994.58V = 1956.5 (7) Å3
Triclinic, P1Z = 2
a = 8.9959 (18) ÅMo Kα radiation
b = 13.947 (3) ŵ = 1.12 mm−1
c = 16.008 (3) ÅT = 293 K
α = 102.71 (3)°0.18 × 0.15 × 0.12 mm
β = 92.37 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		8696 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		5684 reflections with I > 2σ(I)
Tmin = 0.771, Tmax = 0.869Rint = 0.030
19149 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113Δρmax = 0.48 e Å−3
S = 1.04Δρmin = −0.41 e Å−3
8696 reflectionsAbsolute structure: ?
569 parametersFlack parameter: ?
15 restraintsRogers parameter: ?
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Ag10.51631 (4)0.61818 (2)0.156865 (18)0.05298 (11)
Ag20.50633 (5)0.87099 (3)0.205113 (19)0.06856 (14)
C10.0311 (4)0.3785 (3)0.8229 (2)0.0382 (8)
C20.0830 (4)0.2920 (3)0.7783 (2)0.0405 (8)
H20.15720.29340.73980.049*
C30.0281 (4)0.2017 (3)0.7887 (2)0.0422 (8)
C4−0.0854 (4)0.2010 (3)0.8456 (3)0.0480 (9)
C5−0.1369 (4)0.2880 (3)0.8914 (3)0.0532 (10)
H5−0.21120.28690.92990.064*
C6−0.0797 (4)0.3770 (3)0.8810 (3)0.0488 (9)
H6−0.11480.43560.91250.059*
C70.0878 (5)0.1075 (3)0.7394 (3)0.0658 (12)
C80.3217 (4)0.6528 (3)0.6160 (2)0.0485 (10)
H80.32400.58450.60480.058*
C90.2240 (4)0.7004 (4)0.6736 (3)0.0563 (12)
H90.16070.66450.70060.068*
C100.2201 (5)0.8008 (4)0.6910 (2)0.0585 (11)
H100.15430.83340.73000.070*
C110.3149 (4)0.8536 (3)0.6501 (2)0.0474 (9)
H110.31240.92180.66180.057*
C120.4132 (4)0.8056 (3)0.5921 (2)0.0357 (7)
C130.4166 (4)0.7038 (3)0.5745 (2)0.0364 (7)
C140.5186 (4)0.6475 (3)0.5104 (2)0.0495 (9)
H14A0.61480.68180.51650.059*
H14B0.53340.58300.52240.059*
C150.5127 (4)0.8669 (3)0.5488 (2)0.0492 (10)
H15A0.52790.93210.58540.059*
H15B0.60900.83710.54130.059*
C160.3078 (4)0.8984 (3)0.4464 (3)0.0550 (11)
H350.23100.91040.48410.066*
C170.5375 (4)0.6265 (3)0.3517 (2)0.0437 (8)
H170.64080.62440.35170.052*
C180.3123 (4)0.6337 (4)0.3954 (3)0.0584 (11)
H180.23070.63720.42960.070*
C190.3091 (5)0.6254 (4)0.3102 (3)0.0620 (12)
H190.22340.62330.27520.074*
C200.4847 (4)0.6288 (3)−0.0366 (2)0.0393 (8)
H200.38170.6331−0.03670.047*
C210.7098 (5)0.6150 (4)0.0021 (3)0.0675 (13)
H210.79450.60820.03540.081*
C220.7108 (4)0.6219 (4)−0.0795 (3)0.0626 (13)
H220.79320.6204−0.11290.075*
C230.5088 (4)0.6425 (3)−0.1888 (2)0.0374 (8)
H23A0.41090.6703−0.18360.045*
H23B0.49870.5782−0.22740.045*
C240.6103 (3)0.7078 (2)−0.22626 (19)0.0323 (7)
C250.7119 (4)0.6636 (3)−0.2848 (2)0.0470 (9)
H250.71660.5955−0.29900.056*
C260.8063 (4)0.7204 (4)−0.3223 (2)0.0577 (12)
H260.87360.6902−0.36160.069*
C270.8006 (5)0.8198 (4)−0.3016 (3)0.0605 (12)
H270.86500.8577−0.32610.073*
C280.7001 (4)0.8649 (3)−0.2446 (2)0.0496 (10)
H280.69560.9331−0.23180.059*
C290.6049 (4)0.8095 (2)−0.2058 (2)0.0346 (7)
C300.4982 (4)0.8632 (3)−0.1433 (2)0.0419 (8)
H30A0.47840.9265−0.15660.050*
H30B0.40480.8257−0.14940.050*
C310.6986 (4)0.9128 (3)−0.0229 (3)0.0568 (11)
H310.77540.9309−0.05400.068*
C320.7026 (5)0.9151 (3)0.0608 (3)0.0576 (11)
H320.78460.93570.09830.069*
C330.4839 (4)0.8623 (3)0.0121 (2)0.0454 (9)
H330.38540.83950.00850.055*
C340.3000 (5)0.9002 (3)0.3616 (3)0.0586 (11)
H360.21610.91420.33110.070*
C350.5229 (5)0.8640 (3)0.3931 (2)0.0496 (9)
H3240.62250.84800.38880.060*
C360.0543 (6)0.8125 (4)−0.0864 (3)0.0770 (14)
H36A0.00160.8051−0.03720.115*
H36B−0.01070.7942−0.13680.115*
H36C0.08790.8798−0.07930.115*
N10.4492 (3)0.8757 (2)0.46511 (19)0.0432 (7)
N20.4585 (3)0.6358 (2)0.42210 (18)0.0410 (7)
N30.4505 (4)0.6207 (2)0.28299 (18)0.0448 (7)
N40.4359 (4)0.8780 (2)0.3290 (2)0.0524 (8)
N50.5701 (4)0.6192 (2)0.03033 (19)0.0451 (7)
N60.5658 (3)0.6314 (2)−0.10393 (17)0.0341 (6)
N70.5693 (4)0.8829 (2)0.0834 (2)0.0511 (8)
N80.5583 (3)0.8786 (2)−0.05409 (18)0.0384 (7)
O10.0306 (4)0.0287 (2)0.7521 (3)0.0817 (11)
O20.1844 (5)0.1116 (3)0.6878 (3)0.1196 (18)
O3−0.1455 (4)0.1150 (3)0.8567 (2)0.0720 (9)
H4A−0.094 (5)0.068 (3)0.829 (3)0.09 (2)*
O70.1786 (3)0.7512 (2)−0.0952 (2)0.0607 (8)
H7A0.147 (4)0.6923 (12)−0.110 (2)0.045 (12)*
O1W0.1305 (6)0.2310 (5)0.5406 (4)0.1396 (19)
H1A0.0362 (19)0.234 (3)0.533 (6)0.209*
H1B0.156 (7)0.285 (2)0.575 (5)0.209*
O2W0.0029 (6)−0.0585 (5)0.5588 (3)0.1278 (17)
H2A−0.058 (6)−0.040 (7)0.599 (3)0.192*
H2B−0.054 (7)−0.075 (3)0.513 (3)0.192*
O3W0.0648 (7)0.4362 (5)0.5578 (5)0.181 (3)
H3B0.019 (11)0.389 (2)0.523 (6)0.272*
H3A0.005 (7)0.483 (4)0.5640 (14)0.272*
S10.10110 (11)0.49166 (8)0.80514 (8)0.0510 (3)
O40.2488 (10)0.4775 (7)0.7857 (5)0.064 (2)0.676 (12)
O50.0049 (6)0.5169 (5)0.7424 (5)0.076 (3)0.676 (12)
O60.0864 (8)0.5626 (4)0.8905 (4)0.080 (2)0.676 (12)
O6'0.0143 (13)0.5620 (9)0.8224 (13)0.090 (8)0.324 (12)
O5'0.125 (2)0.4631 (10)0.7031 (8)0.107 (7)0.324 (12)
O4'0.253 (2)0.4992 (18)0.8326 (15)0.094 (8)0.324 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0790 (2)0.04833 (19)0.03198 (15)0.00432 (15)0.00483 (14)0.00901 (13)
Ag20.1229 (3)0.0504 (2)0.03425 (17)0.00170 (19)0.01163 (18)0.01212 (14)
C10.0295 (17)0.046 (2)0.0401 (18)−0.0052 (14)−0.0040 (15)0.0122 (16)
C20.0265 (16)0.052 (2)0.044 (2)−0.0043 (15)0.0026 (15)0.0138 (17)
C30.0359 (19)0.047 (2)0.0415 (19)−0.0066 (16)−0.0045 (16)0.0081 (17)
C40.046 (2)0.054 (2)0.046 (2)−0.0101 (18)−0.0058 (18)0.0184 (19)
C50.049 (2)0.068 (3)0.046 (2)−0.002 (2)0.0157 (19)0.020 (2)
C60.050 (2)0.050 (2)0.046 (2)0.0058 (18)0.0076 (18)0.0086 (18)
C70.049 (2)0.053 (3)0.086 (3)−0.004 (2)−0.003 (2)−0.004 (2)
C80.058 (2)0.045 (2)0.046 (2)−0.0104 (18)−0.0092 (19)0.0203 (18)
C90.043 (2)0.089 (4)0.047 (2)−0.009 (2)−0.0020 (19)0.038 (2)
C100.052 (2)0.092 (4)0.0321 (19)0.009 (2)0.0080 (18)0.014 (2)
C110.056 (2)0.051 (2)0.0339 (18)0.0069 (18)0.0001 (18)0.0080 (17)
C120.0412 (19)0.042 (2)0.0247 (15)−0.0017 (15)−0.0018 (14)0.0107 (14)
C130.0413 (19)0.042 (2)0.0259 (15)0.0018 (15)−0.0058 (14)0.0090 (14)
C140.058 (2)0.053 (2)0.0353 (19)0.0108 (19)−0.0033 (18)0.0044 (17)
C150.059 (2)0.052 (2)0.038 (2)−0.0156 (19)−0.0024 (18)0.0166 (18)
C160.045 (2)0.077 (3)0.050 (2)−0.012 (2)0.0021 (19)0.030 (2)
C170.044 (2)0.048 (2)0.0364 (19)0.0062 (17)0.0022 (17)0.0048 (16)
C180.037 (2)0.094 (4)0.039 (2)0.002 (2)−0.0025 (18)0.005 (2)
C190.048 (2)0.092 (4)0.037 (2)0.002 (2)−0.0084 (19)−0.002 (2)
C200.0400 (19)0.040 (2)0.0407 (19)0.0072 (15)0.0024 (16)0.0146 (16)
C210.046 (2)0.107 (4)0.058 (3)0.006 (2)−0.009 (2)0.040 (3)
C220.038 (2)0.100 (4)0.062 (3)0.006 (2)0.003 (2)0.043 (3)
C230.0415 (19)0.0361 (19)0.0362 (17)−0.0049 (14)−0.0052 (15)0.0137 (15)
C240.0323 (17)0.0390 (19)0.0262 (15)−0.0001 (14)−0.0034 (13)0.0096 (14)
C250.047 (2)0.054 (2)0.0364 (19)0.0074 (18)0.0021 (17)0.0011 (17)
C260.037 (2)0.101 (4)0.0346 (19)0.008 (2)0.0062 (17)0.014 (2)
C270.046 (2)0.096 (4)0.047 (2)−0.018 (2)0.004 (2)0.033 (2)
C280.063 (2)0.048 (2)0.040 (2)−0.0165 (19)−0.0027 (19)0.0183 (18)
C290.0394 (18)0.0397 (19)0.0252 (15)−0.0039 (14)−0.0030 (14)0.0098 (14)
C300.050 (2)0.042 (2)0.0331 (17)0.0053 (16)−0.0042 (16)0.0061 (15)
C310.046 (2)0.078 (3)0.042 (2)0.002 (2)0.0054 (19)0.005 (2)
C320.056 (3)0.074 (3)0.038 (2)0.010 (2)−0.0082 (19)0.003 (2)
C330.058 (2)0.036 (2)0.041 (2)−0.0033 (17)0.0071 (18)0.0063 (16)
C340.059 (3)0.070 (3)0.049 (2)−0.018 (2)−0.009 (2)0.023 (2)
C350.063 (3)0.046 (2)0.041 (2)−0.0007 (18)0.0079 (19)0.0134 (18)
C360.071 (3)0.087 (4)0.075 (3)0.013 (3)0.006 (3)0.020 (3)
N10.0487 (18)0.0468 (18)0.0375 (16)−0.0093 (14)−0.0003 (14)0.0181 (14)
N20.0461 (17)0.0435 (18)0.0306 (15)0.0050 (13)−0.0009 (13)0.0019 (13)
N30.0539 (19)0.0479 (19)0.0296 (15)0.0069 (14)−0.0006 (14)0.0020 (13)
N40.074 (2)0.049 (2)0.0354 (16)−0.0094 (17)−0.0016 (17)0.0148 (15)
N50.059 (2)0.0443 (18)0.0344 (16)0.0077 (14)0.0006 (15)0.0135 (14)
N60.0365 (15)0.0330 (15)0.0354 (15)0.0027 (12)−0.0013 (13)0.0139 (12)
N70.071 (2)0.0445 (19)0.0368 (17)0.0072 (16)0.0039 (16)0.0073 (14)
N80.0454 (17)0.0362 (16)0.0320 (15)0.0060 (13)0.0005 (13)0.0035 (12)
O10.077 (2)0.0436 (19)0.118 (3)−0.0043 (16)−0.014 (2)0.0087 (19)
O20.095 (3)0.074 (3)0.172 (5)−0.005 (2)0.076 (3)−0.025 (3)
O30.081 (2)0.066 (2)0.075 (2)−0.027 (2)0.0109 (19)0.0296 (19)
O70.0474 (16)0.064 (2)0.070 (2)−0.0004 (15)0.0075 (15)0.0127 (17)
O1W0.139 (4)0.184 (6)0.093 (4)0.007 (4)0.005 (3)0.026 (4)
O2W0.144 (4)0.152 (5)0.089 (3)0.038 (4)0.023 (3)0.026 (3)
O3W0.181 (6)0.162 (6)0.179 (7)−0.033 (5)0.039 (5)−0.010 (5)
S10.0394 (5)0.0466 (6)0.0711 (7)−0.0050 (4)−0.0040 (5)0.0238 (5)
O40.036 (4)0.057 (4)0.104 (6)0.000 (3)0.022 (5)0.027 (4)
O50.064 (4)0.076 (4)0.102 (5)−0.016 (3)−0.029 (4)0.056 (4)
O60.122 (5)0.041 (3)0.067 (4)−0.019 (3)0.025 (4)−0.009 (2)
O6'0.066 (8)0.056 (7)0.17 (2)0.030 (6)0.050 (12)0.053 (10)
O5'0.165 (17)0.095 (10)0.079 (9)0.003 (10)0.026 (9)0.056 (8)
O4'0.048 (8)0.092 (15)0.160 (19)−0.027 (9)−0.046 (13)0.078 (15)
Geometric parameters (Å, °) top
Ag1—N52.105 (3)C21—H210.93
Ag1—N32.121 (3)C22—N61.364 (5)
Ag2—N42.089 (3)C22—H220.93
Ag2—N72.091 (3)C23—N61.474 (4)
C1—C21.363 (5)C23—C241.506 (4)
C1—C61.393 (5)C23—H23A0.97
C1—S11.770 (3)C23—H23B0.97
C2—C31.387 (5)C24—C291.387 (5)
C2—H20.93C24—C251.392 (5)
C3—C41.397 (5)C25—C261.388 (6)
C3—C71.500 (6)C25—H250.93
C4—O31.354 (5)C26—C271.355 (7)
C4—C51.374 (6)C26—H260.93
C5—C61.379 (5)C27—C281.374 (6)
C5—H50.93C27—H270.93
C6—H60.93C28—C291.393 (4)
C7—O21.233 (6)C28—H280.93
C7—O11.263 (5)C29—C301.505 (5)
C8—C91.375 (6)C30—N81.475 (4)
C8—C131.380 (5)C30—H30A0.97
C8—H80.93C30—H30B0.97
C9—C101.368 (6)C31—C321.332 (5)
C9—H90.93C31—N81.372 (5)
C10—C111.389 (5)C31—H310.93
C10—H100.93C32—N71.361 (5)
C11—C121.383 (5)C32—H320.93
C11—H110.93C33—N71.323 (5)
C12—C131.387 (5)C33—N81.333 (5)
C12—C151.513 (4)C33—H330.93
C13—C141.506 (5)C34—N41.365 (5)
C14—N21.467 (4)C34—H360.93
C14—H14A0.97C35—N41.317 (5)
C14—H14B0.97C35—N11.334 (5)
C15—N11.466 (5)C35—H3240.93
C15—H15A0.97C36—O71.416 (6)
C15—H15B0.97C36—H36A0.96
C16—N11.355 (5)C36—H36B0.96
C16—C341.361 (5)C36—H36C0.96
C16—H350.93O3—H4A0.86 (4)
C17—N31.311 (5)O7—H7A0.842 (10)
C17—N21.341 (4)O1W—H1A0.856 (10)
C17—H170.93O1W—H1B0.85 (6)
C18—C191.343 (5)O2W—H2A0.86 (5)
C18—N21.363 (5)O2W—H2B0.86 (5)
C18—H180.93O3W—H3B0.85 (7)
C19—N31.360 (5)O3W—H3A0.85 (6)
C19—H190.93S1—O6'1.258 (10)
C20—N51.326 (5)S1—O41.386 (9)
C20—N61.332 (4)S1—O51.407 (5)
C20—H200.93S1—O4'1.42 (2)
C21—C221.330 (6)S1—O61.514 (5)
C21—N51.351 (5)S1—O5'1.619 (13)
N5—Ag1—N3176.76 (13)C27—C26—H26120.0
N4—Ag2—N7172.60 (13)C25—C26—H26120.0
C2—C1—C6119.5 (3)C26—C27—C28120.4 (3)
C2—C1—S1120.1 (3)C26—C27—H27119.8
C6—C1—S1120.4 (3)C28—C27—H27119.8
C1—C2—C3121.9 (3)C27—C28—C29120.7 (4)
C1—C2—H2119.1C27—C28—H28119.7
C3—C2—H2119.1C29—C28—H28119.7
C2—C3—C4118.2 (4)C24—C29—C28119.4 (3)
C2—C3—C7120.9 (4)C24—C29—C30122.4 (3)
C4—C3—C7120.9 (4)C28—C29—C30118.2 (3)
O3—C4—C5119.2 (4)N8—C30—C29111.6 (3)
O3—C4—C3120.7 (4)N8—C30—H30A109.3
C5—C4—C3120.2 (3)C29—C30—H30A109.3
C4—C5—C6120.8 (4)N8—C30—H30B109.3
C4—C5—H5119.6C29—C30—H30B109.3
C6—C5—H5119.6H30A—C30—H30B108.0
C5—C6—C1119.5 (4)C32—C31—N8106.3 (4)
C5—C6—H6120.2C32—C31—H31126.8
C1—C6—H6120.2N8—C31—H31126.8
O2—C7—O1124.5 (5)C31—C32—N7110.2 (4)
O2—C7—C3118.7 (4)C31—C32—H32124.9
O1—C7—C3116.8 (4)N7—C32—H32124.9
C9—C8—C13121.6 (4)N7—C33—N8110.8 (3)
C9—C8—H8119.2N7—C33—H33124.6
C13—C8—H8119.2N8—C33—H33124.6
C10—C9—C8119.8 (3)C16—C34—N4108.6 (4)
C10—C9—H9120.1C16—C34—H36125.7
C8—C9—H9120.1N4—C34—H36125.7
C9—C10—C11119.6 (4)N4—C35—N1111.0 (4)
C9—C10—H10120.2N4—C35—H324124.5
C11—C10—H10120.2N1—C35—H324124.5
C12—C11—C10120.6 (4)O7—C36—H36A109.5
C12—C11—H11119.7O7—C36—H36B109.5
C10—C11—H11119.7H36A—C36—H36B109.5
C11—C12—C13119.6 (3)O7—C36—H36C109.5
C11—C12—C15118.3 (3)H36A—C36—H36C109.5
C13—C12—C15122.1 (3)H36B—C36—H36C109.5
C8—C13—C12118.8 (3)C35—N1—C16107.4 (3)
C8—C13—C14119.2 (3)C35—N1—C15125.4 (4)
C12—C13—C14122.0 (3)C16—N1—C15127.1 (3)
N2—C14—C13111.9 (3)C17—N2—C18106.6 (3)
N2—C14—H14A109.2C17—N2—C14126.4 (3)
C13—C14—H14A109.2C18—N2—C14127.0 (3)
N2—C14—H14B109.2C17—N3—C19106.0 (3)
C13—C14—H14B109.2C17—N3—Ag1127.2 (3)
H14A—C14—H14B107.9C19—N3—Ag1126.6 (3)
N1—C15—C12112.1 (3)C35—N4—C34106.2 (3)
N1—C15—H15A109.2C35—N4—Ag2124.1 (3)
C12—C15—H15A109.2C34—N4—Ag2129.6 (3)
N1—C15—H15B109.2C20—N5—C21104.6 (3)
C12—C15—H15B109.2C20—N5—Ag1130.7 (3)
H15A—C15—H15B107.9C21—N5—Ag1124.5 (3)
N1—C16—C34106.7 (4)C20—N6—C22107.2 (3)
N1—C16—H35126.7C20—N6—C23126.2 (3)
C34—C16—H35126.7C22—N6—C23126.6 (3)
N3—C17—N2111.2 (3)C33—N7—C32105.6 (3)
N3—C17—H17124.4C33—N7—Ag2126.2 (3)
N2—C17—H17124.4C32—N7—Ag2128.2 (3)
C19—C18—N2106.7 (4)C33—N8—C31107.1 (3)
C19—C18—H18126.6C33—N8—C30125.6 (3)
N2—C18—H18126.6C31—N8—C30127.3 (3)
C18—C19—N3109.5 (4)C4—O3—H4A108 (4)
C18—C19—H19125.3C36—O7—H7A108 (3)
N3—C19—H19125.3H1A—O1W—H1B104 (6)
N5—C20—N6111.1 (3)H2A—O2W—H2B104 (5)
N5—C20—H20124.4H3B—O3W—H3A105 (7)
N6—C20—H20124.4O6'—S1—O4138.1 (6)
C22—C21—N5111.3 (4)O6'—S1—O557.8 (9)
C22—C21—H21124.3O4—S1—O5117.4 (5)
N5—C21—H21124.3O6'—S1—O4'123.3 (13)
C21—C22—N6105.7 (4)O5—S1—O4'140.5 (9)
C21—C22—H22127.1O6'—S1—O652.4 (9)
N6—C22—H22127.1O4—S1—O6111.7 (4)
N6—C23—C24111.8 (3)O5—S1—O6110.1 (5)
N6—C23—H23A109.2O4'—S1—O682.2 (10)
C24—C23—H23A109.2O6'—S1—O5'110.1 (10)
N6—C23—H23B109.2O4—S1—O5'66.9 (7)
C24—C23—H23B109.2O5—S1—O5'55.4 (6)
H23A—C23—H23B107.9O4'—S1—O5'97.3 (10)
C29—C24—C25118.9 (3)O6—S1—O5'154.3 (5)
C29—C24—C23122.8 (3)O6'—S1—C1115.0 (5)
C25—C24—C23118.3 (3)O4—S1—C1106.3 (4)
C26—C25—C24120.6 (4)O5—S1—C1106.6 (2)
C26—C25—H25119.7O4'—S1—C1106.4 (9)
C24—C25—H25119.7O6—S1—C1103.6 (2)
C27—C26—C25120.0 (4)O5'—S1—C1101.2 (5)
C6—C1—C2—C30.3 (5)N4—C35—N1—C15−179.0 (3)
S1—C1—C2—C3−178.2 (3)C34—C16—N1—C35−0.3 (5)
C1—C2—C3—C41.2 (5)C34—C16—N1—C15178.8 (4)
C1—C2—C3—C7−179.5 (4)C12—C15—N1—C35−133.8 (4)
C2—C3—C4—O3178.4 (3)C12—C15—N1—C1647.3 (5)
C7—C3—C4—O3−0.9 (6)N3—C17—N2—C181.3 (5)
C2—C3—C4—C5−1.9 (6)N3—C17—N2—C14−177.9 (3)
C7—C3—C4—C5178.8 (4)C19—C18—N2—C17−1.4 (5)
O3—C4—C5—C6−179.1 (4)C19—C18—N2—C14177.8 (4)
C3—C4—C5—C61.2 (6)C13—C14—N2—C17151.7 (3)
C4—C5—C6—C10.3 (6)C13—C14—N2—C18−27.4 (6)
C2—C1—C6—C5−1.1 (6)N2—C17—N3—C19−0.7 (5)
S1—C1—C6—C5177.4 (3)N2—C17—N3—Ag1174.1 (2)
C2—C3—C7—O2−1.7 (7)C18—C19—N3—C17−0.2 (5)
C4—C3—C7—O2177.6 (5)C18—C19—N3—Ag1−175.0 (3)
C2—C3—C7—O1−179.3 (4)N1—C35—N4—C340.2 (4)
C4—C3—C7—O1−0.1 (6)N1—C35—N4—Ag2178.2 (2)
C13—C8—C9—C10−0.3 (6)C16—C34—N4—C35−0.4 (5)
C8—C9—C10—C110.1 (6)C16—C34—N4—Ag2−178.3 (3)
C9—C10—C11—C120.0 (6)N6—C20—N5—C21−0.5 (4)
C10—C11—C12—C130.2 (5)N6—C20—N5—Ag1176.2 (2)
C10—C11—C12—C15179.4 (3)C22—C21—N5—C200.0 (6)
C9—C8—C13—C120.5 (5)C22—C21—N5—Ag1−176.9 (3)
C9—C8—C13—C14−178.5 (3)N5—C20—N6—C220.7 (4)
C11—C12—C13—C8−0.4 (5)N5—C20—N6—C23−179.3 (3)
C15—C12—C13—C8−179.6 (3)C21—C22—N6—C20−0.7 (5)
C11—C12—C13—C14178.6 (3)C21—C22—N6—C23179.4 (4)
C15—C12—C13—C14−0.6 (5)C24—C23—N6—C20140.9 (3)
C8—C13—C14—N298.4 (4)C24—C23—N6—C22−39.1 (5)
C12—C13—C14—N2−80.5 (4)N8—C33—N7—C321.0 (4)
C11—C12—C15—N1−94.9 (4)N8—C33—N7—Ag2179.6 (2)
C13—C12—C15—N184.3 (4)C31—C32—N7—C33−0.8 (5)
N2—C18—C19—N31.0 (6)C31—C32—N7—Ag2−179.3 (3)
N5—C21—C22—N60.4 (6)N7—C33—N8—C31−0.9 (4)
N6—C23—C24—C29−83.6 (4)N7—C33—N8—C30179.8 (3)
N6—C23—C24—C2597.4 (4)C32—C31—N8—C330.3 (5)
C29—C24—C25—C260.0 (5)C32—C31—N8—C30179.7 (4)
C23—C24—C25—C26179.0 (3)C29—C30—N8—C33−133.9 (3)
C24—C25—C26—C270.3 (6)C29—C30—N8—C3146.9 (5)
C25—C26—C27—C28−1.0 (6)C2—C1—S1—O6'154.7 (11)
C26—C27—C28—C291.4 (6)C6—C1—S1—O6'−23.8 (11)
C25—C24—C29—C280.4 (5)C2—C1—S1—O4−33.0 (5)
C23—C24—C29—C28−178.5 (3)C6—C1—S1—O4148.5 (5)
C25—C24—C29—C30179.9 (3)C2—C1—S1—O593.0 (5)
C23—C24—C29—C300.9 (5)C6—C1—S1—O5−85.5 (5)
C27—C28—C29—C24−1.1 (5)C2—C1—S1—O4'−65.1 (11)
C27—C28—C29—C30179.4 (3)C6—C1—S1—O4'116.4 (11)
C24—C29—C30—N884.9 (4)C2—C1—S1—O6−150.8 (4)
C28—C29—C30—N8−95.6 (4)C6—C1—S1—O630.7 (5)
N8—C31—C32—N70.3 (5)C2—C1—S1—O5'36.1 (7)
N1—C16—C34—N40.4 (5)C6—C1—S1—O5'−142.4 (7)
N4—C35—N1—C160.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O3W0.85 (6)2.35 (5)2.892 (9)122 (4)
O2W—H2A···O10.86 (5)2.52 (6)3.063 (7)122 (6)
O3—H4A···O10.86 (4)1.71 (3)2.486 (6)149 (5)
O7—H7A···O6i0.84 (1)1.88 (2)2.697 (6)164 (4)
O2W—H2B···O1Wii0.86 (5)2.24 (5)2.790 (9)122 (4)
O3W—H3A···O3Wiii0.85 (6)2.52 (4)3.053 (10)122 (2)
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N52.105 (3)Ag2—N42.089 (3)
Ag1—N32.121 (3)Ag2—N72.091 (3)
N5—Ag1—N3176.76 (13)N4—Ag2—N7172.60 (13)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O3W0.85 (6)2.35 (5)2.892 (9)122 (4)
O2W—H2A···O10.86 (5)2.52 (6)3.063 (7)122 (6)
O3—H4A···O10.86 (4)1.71 (3)2.486 (6)149 (5)
O7—H7A···O6i0.84 (1)1.88 (2)2.697 (6)164 (4)
O2W—H2B···O1Wii0.86 (5)2.24 (5)2.790 (9)122 (4)
O3W—H3A···O3Wiii0.85 (6)2.52 (4)3.053 (10)122 (2)
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1.
Acknowledgements top

The authors thank the Science Foundation of Suihua University (grant No. K081001) for supporting this work.

references
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