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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1071.
Published online 2008 July 26. doi:  10.1107/S1600536808023052
PMCID: PMC2961981

Bis[μ-1,2-bis­(1H-imidazol-1-ylmethyl)benzene-κ2 N 3:N 3′]disilver(I) bis­(4-amino-2,5-dichloro­benzene­sulfonate) tetra­hydrate

Abstract

The asymmetric unit of the title compound, [Ag2(C14H14N4)2](C6H4Cl2NO3S)2·4H2O, contains one-half of each of two independent dicationic units, two 4-amino-2,5-dichloro­benzene­sulfonate anions and four water mol­ecules. Each centrosymmetric dicationic unit has a dinuclear structure in which two AgI atoms are bridged by two 1,2-bis­(1H-imidazol-1-yl­meth­yl)benzene ligands in a slightly distorted linear coordination geometry. The 4-amino-2,5-dichloro­benzene­sulfonate anion does not coordinate with the AgI center, acting only as a counteranion. In the crystal structure, inter­molecular O—H(...)O and N—H(...)O hydrogen bonds form a three-dimensional network.

Related literature

For related literature, see: Aakeröy & Beatty (1998 [triangle]); Cote & Shimizu (2004 [triangle]); Feazell et al. (2006 [triangle]); Li et al. (2006 [triangle]); Liu et al. (2007 [triangle]); Ma et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1071-scheme1.jpg

Experimental

Crystal data

  • [Ag2(C14H14N4)2](C6H4Cl2NO3S)2·4H2O
  • M r = 1246.51
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1071-efi1.jpg
  • a = 11.732 (6) Å
  • b = 14.598 (6) Å
  • c = 15.718 (6) Å
  • α = 79.068 (12)°
  • β = 72.843 (19)°
  • γ = 70.991 (17)°
  • V = 2418.8 (18) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.18 mm−1
  • T = 293 (2) K
  • 0.35 × 0.25 × 0.24 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.716, T max = 0.753
  • 19762 measured reflections
  • 10576 independent reflections
  • 6897 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.152
  • S = 0.96
  • 10576 reflections
  • 649 parameters
  • 13 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.92 e Å−3
  • Δρmin = −0.36 e Å−3

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

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023052/ci2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023052/ci2638Isup2.hkl

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

Acknowledgments

The authors thank the Science Foundation of Suihua University (grant No. K071001) for supporting this work.

supplementary crystallographic information

Comment

AgI complexes have shown versatility of their coordination geometry (Aakeröy & Beatty, 1998; 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). Herein, we present a new silver-sulfonate complex, namely [Ag2(IBI)2]L2.4H2O, where IBI is 1,2-bis ((1H-imidazol-1-yl)methyl)benzene and L is 4-amino-2,5-dichlorobenzenesulfonic acid.

Selected bond distances and angles are listed in Table 1. The asymmetric unit of the title compound contains one-half each of two independent dicationic units, two 4-amino-2,5-dichlorobenzenesulfonate anions and four water molecules. Each AgI ion is two-coordinated by two N atoms from two IBI ligands, showing a slightly distorted linear geometry. The Ag—N bond distances are within the normal range observed in N-containing AgI complexes (Li et al., 2006; Feazell et al., 2006). The L anion does not coordinate with silver ion but acts as a counteranion.

N—H···O and O—H···O hydrogen bonds between water molecules and L ligands result in the formation of a three-dimensional supramolecular structure (Table 2).

Experimental

An aqueous solution (10 ml) of 4-amino-2,5-dichlorobenzenesulfonic acid (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 6 d at room temperature.

Refinement

H atoms bonded to N atoms were located in a difference map and refined with a N—H distance restraint of 0.85 (3) Å and with Uiso(H) = 1.5Ueq(N). Water H atoms were located in a difference Fourier map and refined with O—H and H···H distance restraints of 0.85 (3) Å and 1.30 (3) Å, respectively, and with Uiso(H) = 1.5Ueq(O). 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 highest residual density peak is located 0.89 Å from atom Ag2 and the deepest hole is located 1.54 Å from atom Ag1.

Figures

Fig. 1.
The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) 1-x, 1-y, 2-z; (ii) 2-x, -y, 1-z.

Crystal data

[Ag2(C14H14N4)2](C6H4Cl2N1O3S)2·4H2OZ = 2
Mr = 1246.51F000 = 1256
Triclinic, P1Dx = 1.712 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71069 Å
a = 11.732 (6) ÅCell parameters from 10576 reflections
b = 14.598 (6) Åθ = 3.0–27.5º
c = 15.718 (6) ŵ = 1.18 mm1
α = 79.068 (12)ºT = 293 (2) K
β = 72.843 (19)ºBlock, colourless
γ = 70.991 (17)º0.35 × 0.25 × 0.24 mm
V = 2418.8 (18) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer10576 independent reflections
Radiation source: fine-focus sealed tube6897 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.0º
ω scansh = −15→15
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)k = −18→18
Tmin = 0.716, Tmax = 0.753l = −20→19
19762 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152  w = 1/[σ2(Fo2) + (0.0975P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.002
10576 reflectionsΔρmax = 0.92 e Å3
649 parametersΔρmin = −0.36 e Å3
13 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C10.8198 (3)0.6791 (2)0.2186 (2)0.0354 (7)
C20.7330 (3)0.7577 (2)0.1876 (2)0.0366 (7)
H20.72020.75900.13170.044*
C30.6652 (3)0.8340 (2)0.2383 (2)0.0388 (7)
C40.6792 (4)0.8342 (2)0.3238 (2)0.0438 (8)
C50.7666 (3)0.7540 (2)0.3548 (2)0.0427 (8)
H50.77840.75160.41130.051*
C60.8349 (3)0.6793 (2)0.3037 (2)0.0356 (7)
C70.3133 (4)0.2224 (2)0.3052 (2)0.0443 (8)
C80.1970 (4)0.2875 (2)0.3230 (2)0.0475 (9)
C90.1282 (4)0.3219 (3)0.2605 (2)0.0480 (9)
H90.05050.36740.27510.058*
C100.1729 (4)0.2898 (3)0.1759 (2)0.0474 (9)
C110.2901 (4)0.2236 (2)0.1576 (2)0.0470 (9)
C120.3595 (4)0.1902 (2)0.2207 (3)0.0458 (8)
H120.43800.14570.20620.055*
C130.4409 (4)0.3953 (3)0.8315 (3)0.0484 (9)
H130.37340.45110.83550.058*
C140.5857 (4)0.2737 (3)0.8637 (3)0.0601 (11)
H140.63930.22890.89530.072*
C150.5879 (4)0.2697 (3)0.7782 (3)0.0538 (10)
H150.64130.22270.74060.065*
C160.2850 (4)0.5007 (3)1.1974 (3)0.0592 (11)
H160.21680.53001.17310.071*
C170.2902 (4)0.5130 (3)1.2789 (3)0.0562 (10)
H170.22820.55131.32070.067*
C180.4640 (4)0.4143 (3)1.2125 (3)0.0525 (9)
H180.54430.37191.20190.063*
C190.4582 (5)0.4438 (3)1.3650 (3)0.0597 (12)
H19A0.54670.43721.34400.072*
H19B0.44810.38391.40120.072*
C200.6035 (4)0.4727 (3)0.5778 (2)0.0473 (9)
C210.7006 (5)0.4807 (4)0.5034 (3)0.0672 (13)
H210.72720.53630.49120.081*
C220.7575 (5)0.4091 (5)0.4482 (3)0.0814 (17)
H220.82230.41630.39880.098*
C230.7203 (5)0.3264 (5)0.4645 (3)0.0805 (16)
H230.76000.27720.42680.097*
C240.6223 (5)0.3165 (3)0.5383 (3)0.0597 (11)
H240.59580.26090.54940.072*
C250.5645 (4)0.3890 (3)0.5949 (2)0.0426 (8)
C260.4588 (4)0.3750 (3)0.6729 (2)0.0513 (9)
H26A0.39060.43470.67670.062*
H26B0.42930.32410.66290.062*
C270.9272 (5)0.2163 (3)0.6345 (3)0.0624 (11)
H270.87720.26680.60420.075*
C280.9248 (4)0.2116 (3)0.7213 (3)0.0602 (11)
H280.87420.25640.76160.072*
C291.0624 (4)0.0856 (3)0.6622 (3)0.0555 (10)
H291.12520.02700.65610.067*
C301.2267 (4)−0.0007 (3)0.2968 (3)0.0548 (10)
H301.2907−0.03380.32460.066*
C311.2282 (4)−0.0092 (3)0.2127 (3)0.0529 (9)
H311.2920−0.04780.17210.064*
C321.0534 (4)0.0933 (3)0.2743 (3)0.0556 (10)
H320.97460.13790.28230.067*
C331.0740 (5)0.0685 (3)0.1172 (3)0.0587 (11)
H33A1.10580.11880.07710.070*
H33B0.98370.09200.13230.070*
C340.8843 (4)0.0216 (3)0.9298 (2)0.0479 (9)
C350.7849 (5)0.0306 (4)1.0058 (3)0.0628 (12)
H350.7457−0.01841.02470.075*
C360.7438 (5)0.1089 (4)1.0529 (3)0.0759 (14)
H360.67810.11271.10390.091*
C370.7994 (6)0.1817 (4)1.0251 (3)0.0802 (15)
H370.77050.23601.05670.096*
C380.8985 (5)0.1757 (4)0.9501 (3)0.0682 (13)
H380.93600.22570.93180.082*
C390.9421 (4)0.0953 (3)0.9020 (2)0.0525 (10)
C401.0505 (4)0.0916 (4)0.8221 (3)0.0634 (12)
H40A1.09910.13080.82930.076*
H40B1.10340.02490.81900.076*
N11.1171 (3)0.0505 (2)0.1992 (2)0.0470 (7)
N21.1180 (4)0.0633 (3)0.3353 (2)0.0544 (8)
N31.0130 (4)0.1370 (3)0.5975 (2)0.0584 (9)
N41.0121 (3)0.1272 (2)0.7374 (2)0.0509 (8)
N50.1005 (4)0.3204 (3)0.1159 (3)0.0668 (11)
H5A0.041 (4)0.371 (3)0.130 (4)0.100*
H5B0.140 (6)0.309 (4)0.066 (4)0.100*
N60.6122 (5)0.9084 (3)0.3745 (3)0.0742 (13)
H6A0.622 (6)0.912 (4)0.424 (3)0.111*
H6B0.580 (6)0.960 (3)0.351 (4)0.111*
N70.4956 (3)0.3487 (2)0.75842 (19)0.0425 (7)
N80.4938 (3)0.3527 (2)0.8973 (2)0.0516 (8)
N90.3948 (3)0.4387 (2)1.1558 (2)0.0516 (8)
N100.4063 (3)0.4572 (2)1.2871 (2)0.0457 (7)
O10.4075 (4)0.2441 (2)0.4284 (2)0.0799 (11)
O20.5249 (3)0.1193 (2)0.3297 (2)0.0792 (10)
O1W0.2170 (4)0.5412 (3)0.9721 (2)0.0832 (11)
H1A0.169 (7)0.563 (5)1.016 (4)0.125*
H1B0.178 (6)0.515 (4)0.953 (4)0.125*
O30.3444 (3)0.1006 (2)0.4441 (2)0.0727 (10)
O2W0.7688 (5)0.3506 (4)0.1994 (4)0.1072 (15)
H2A0.810 (8)0.375 (6)0.216 (5)0.161*
H2B0.794 (8)0.356 (6)0.144 (2)0.161*
O41.0322 (3)0.5854 (3)0.1273 (2)0.0742 (9)
O3W0.7592 (4)0.1554 (4)0.2732 (4)0.1118 (16)
H3A0.691 (5)0.145 (5)0.285 (6)0.168*
H3B0.746 (7)0.214 (3)0.254 (5)0.168*
O50.8507 (3)0.6085 (2)0.07362 (17)0.0578 (7)
O4W0.2819 (6)0.9250 (4)0.5166 (4)0.1301 (19)
H4A0.299 (8)0.963 (6)0.542 (6)0.195*
H4B0.354 (5)0.902 (7)0.480 (5)0.195*
O60.8852 (3)0.49480 (18)0.2017 (2)0.0645 (8)
S10.40489 (11)0.16866 (7)0.38332 (8)0.0534 (3)
S20.90401 (9)0.58453 (7)0.15024 (6)0.0444 (2)
Ag10.44041 (4)0.40061 (3)1.02509 (2)0.06083 (13)
Ag21.06711 (4)0.09945 (3)0.46655 (2)0.06964 (14)
Cl10.94358 (9)0.58423 (6)0.34728 (6)0.0462 (2)
Cl20.55802 (10)0.93124 (7)0.19615 (7)0.0550 (3)
Cl30.12837 (12)0.33250 (8)0.42796 (7)0.0687 (3)
Cl40.35254 (12)0.17913 (8)0.05280 (7)0.0663 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0315 (18)0.0399 (16)0.0357 (15)−0.0105 (14)−0.0085 (13)−0.0052 (14)
C20.0325 (18)0.0433 (17)0.0334 (15)−0.0118 (14)−0.0083 (13)−0.0006 (14)
C30.0345 (19)0.0360 (16)0.0422 (17)−0.0089 (14)−0.0091 (14)0.0014 (15)
C40.049 (2)0.0370 (16)0.0439 (18)−0.0071 (15)−0.0124 (16)−0.0087 (15)
C50.048 (2)0.0433 (17)0.0387 (17)−0.0096 (16)−0.0154 (16)−0.0070 (15)
C60.0338 (18)0.0354 (15)0.0388 (16)−0.0109 (13)−0.0118 (14)−0.0005 (14)
C70.054 (2)0.0309 (15)0.049 (2)−0.0136 (15)−0.0180 (17)0.0035 (15)
C80.057 (2)0.0329 (16)0.0454 (19)−0.0040 (16)−0.0121 (17)−0.0037 (15)
C90.052 (2)0.0379 (17)0.0407 (18)0.0017 (16)−0.0082 (17)−0.0048 (15)
C100.055 (2)0.0391 (17)0.0422 (18)−0.0104 (17)−0.0107 (17)0.0027 (16)
C110.059 (3)0.0356 (16)0.0442 (19)−0.0200 (17)−0.0040 (17)−0.0021 (15)
C120.046 (2)0.0318 (16)0.053 (2)−0.0083 (15)−0.0046 (17)−0.0069 (16)
C130.042 (2)0.0469 (19)0.048 (2)−0.0110 (16)−0.0016 (17)−0.0048 (17)
C140.064 (3)0.058 (2)0.048 (2)−0.006 (2)−0.017 (2)0.0007 (19)
C150.058 (3)0.049 (2)0.0436 (19)−0.0066 (18)−0.0071 (18)−0.0067 (17)
C160.053 (3)0.080 (3)0.055 (2)−0.019 (2)−0.022 (2)−0.017 (2)
C170.048 (2)0.076 (3)0.052 (2)−0.018 (2)−0.0129 (19)−0.022 (2)
C180.056 (3)0.050 (2)0.057 (2)−0.0168 (19)−0.019 (2)−0.0073 (19)
C190.088 (3)0.047 (2)0.060 (2)−0.021 (2)−0.043 (2)0.0001 (19)
C200.059 (3)0.057 (2)0.0376 (17)−0.0276 (19)−0.0206 (17)0.0026 (17)
C210.079 (3)0.100 (3)0.041 (2)−0.059 (3)−0.018 (2)0.011 (2)
C220.065 (3)0.144 (5)0.043 (2)−0.049 (4)−0.009 (2)−0.001 (3)
C230.081 (4)0.110 (4)0.047 (2)−0.012 (3)−0.015 (2)−0.030 (3)
C240.073 (3)0.060 (2)0.051 (2)−0.020 (2)−0.017 (2)−0.013 (2)
C250.048 (2)0.0498 (19)0.0366 (16)−0.0219 (17)−0.0159 (16)0.0032 (16)
C260.051 (2)0.064 (2)0.0449 (19)−0.026 (2)−0.0159 (18)0.0026 (18)
C270.075 (3)0.061 (2)0.049 (2)−0.020 (2)−0.017 (2)0.004 (2)
C280.063 (3)0.064 (3)0.047 (2)−0.020 (2)−0.005 (2)−0.001 (2)
C290.054 (3)0.058 (2)0.053 (2)−0.020 (2)−0.0076 (19)−0.004 (2)
C300.056 (3)0.056 (2)0.055 (2)−0.0096 (19)−0.022 (2)−0.0115 (19)
C310.051 (3)0.057 (2)0.053 (2)−0.0085 (19)−0.0183 (19)−0.0155 (18)
C320.050 (3)0.062 (2)0.058 (2)−0.017 (2)−0.015 (2)−0.013 (2)
C330.074 (3)0.057 (2)0.054 (2)−0.021 (2)−0.033 (2)0.0028 (19)
C340.049 (2)0.064 (2)0.0389 (17)−0.0257 (19)−0.0177 (17)0.0020 (17)
C350.064 (3)0.086 (3)0.047 (2)−0.035 (3)−0.016 (2)0.002 (2)
C360.071 (4)0.108 (4)0.047 (2)−0.024 (3)−0.010 (2)−0.013 (3)
C370.102 (5)0.089 (4)0.058 (3)−0.020 (3)−0.031 (3)−0.025 (3)
C380.089 (4)0.076 (3)0.060 (3)−0.042 (3)−0.034 (3)0.002 (2)
C390.060 (3)0.069 (2)0.0423 (19)−0.031 (2)−0.0258 (18)0.0057 (19)
C400.054 (3)0.096 (3)0.051 (2)−0.039 (2)−0.017 (2)0.006 (2)
N10.052 (2)0.0457 (16)0.0515 (17)−0.0198 (15)−0.0194 (15)−0.0032 (14)
N20.062 (2)0.060 (2)0.0488 (18)−0.0249 (18)−0.0172 (17)−0.0071 (16)
N30.070 (3)0.0564 (19)0.0496 (19)−0.0232 (18)−0.0090 (17)−0.0071 (17)
N40.050 (2)0.0619 (19)0.0448 (17)−0.0266 (17)−0.0124 (15)0.0048 (16)
N50.071 (3)0.068 (2)0.0485 (19)0.001 (2)−0.023 (2)−0.0029 (19)
N60.100 (3)0.0504 (19)0.061 (2)0.016 (2)−0.036 (2)−0.0224 (18)
N70.0403 (18)0.0440 (15)0.0406 (15)−0.0167 (13)−0.0046 (13)0.0010 (13)
N80.058 (2)0.0554 (18)0.0439 (16)−0.0223 (16)−0.0093 (15)−0.0044 (15)
N90.058 (2)0.0583 (19)0.0448 (17)−0.0223 (17)−0.0136 (16)−0.0088 (15)
N100.055 (2)0.0435 (15)0.0468 (16)−0.0206 (15)−0.0211 (15)−0.0006 (14)
O10.116 (3)0.0512 (16)0.099 (2)−0.0303 (18)−0.061 (2)−0.0044 (17)
O20.059 (2)0.0723 (19)0.103 (3)−0.0016 (17)−0.033 (2)−0.0103 (19)
O1W0.067 (3)0.118 (3)0.067 (2)−0.034 (2)0.0094 (17)−0.043 (2)
O30.098 (3)0.0560 (16)0.077 (2)−0.0340 (17)−0.046 (2)0.0235 (16)
O2W0.092 (3)0.108 (3)0.131 (4)−0.050 (3)−0.020 (3)−0.010 (3)
O40.0386 (18)0.113 (3)0.0653 (18)−0.0073 (17)−0.0007 (14)−0.0401 (18)
O3W0.069 (3)0.094 (3)0.165 (5)−0.008 (2)−0.041 (3)−0.005 (3)
O50.067 (2)0.0644 (16)0.0407 (13)−0.0052 (14)−0.0208 (13)−0.0158 (12)
O4W0.188 (6)0.085 (3)0.127 (4)−0.043 (4)−0.051 (4)−0.010 (3)
O60.095 (2)0.0394 (13)0.0644 (17)−0.0098 (14)−0.0358 (17)−0.0090 (13)
S10.0593 (7)0.0375 (4)0.0692 (6)−0.0130 (4)−0.0298 (5)0.0011 (4)
S20.0410 (5)0.0485 (5)0.0396 (4)−0.0005 (4)−0.0116 (4)−0.0141 (4)
Ag10.0758 (3)0.0704 (2)0.04346 (17)−0.03161 (18)−0.00942 (15)−0.01273 (15)
Ag20.0871 (3)0.0778 (2)0.04749 (19)−0.0295 (2)−0.01030 (17)−0.01494 (17)
Cl10.0453 (5)0.0444 (4)0.0475 (5)−0.0044 (4)−0.0209 (4)−0.0021 (4)
Cl20.0497 (6)0.0453 (5)0.0618 (6)0.0019 (4)−0.0213 (5)−0.0022 (4)
Cl30.0803 (8)0.0638 (6)0.0436 (5)0.0058 (5)−0.0142 (5)−0.0120 (5)
Cl40.0791 (8)0.0626 (6)0.0467 (5)−0.0158 (6)0.0014 (5)−0.0164 (5)

Geometric parameters (Å, °)

C1—C21.382 (4)C26—H26B0.97
C1—C61.401 (4)C27—C281.345 (6)
C1—S21.756 (3)C27—N31.357 (6)
C2—C31.377 (5)C27—H270.93
C2—H20.93C28—N41.358 (6)
C3—C41.402 (5)C28—H280.93
C3—Cl21.734 (3)C29—N31.308 (5)
C4—N61.353 (5)C29—N41.319 (5)
C4—C51.398 (5)C29—H290.93
C5—C61.364 (5)C30—C311.346 (6)
C5—H50.93C30—N21.360 (6)
C6—Cl11.738 (3)C30—H300.93
C7—C81.369 (5)C31—N11.363 (5)
C7—C121.387 (5)C31—H310.93
C7—S11.773 (4)C32—N21.317 (5)
C8—C91.373 (5)C32—N11.341 (5)
C8—Cl31.756 (4)C32—H320.93
C9—C101.388 (5)C33—N11.468 (5)
C9—H90.93C33—C34ii1.499 (6)
C10—N51.371 (5)C33—H33A0.97
C10—C111.383 (6)C33—H33B0.97
C11—C121.385 (5)C34—C391.390 (5)
C11—Cl41.748 (4)C34—C351.393 (6)
C12—H120.93C34—C33ii1.499 (6)
C13—N81.313 (5)C35—C361.355 (7)
C13—N71.331 (5)C35—H350.93
C13—H130.93C36—C371.362 (8)
C14—C151.350 (6)C36—H360.93
C14—N81.362 (6)C37—C381.383 (8)
C14—H140.93C37—H370.93
C15—N71.359 (5)C38—C391.388 (7)
C15—H150.93C38—H380.93
C16—C171.349 (6)C39—C401.495 (6)
C16—N91.369 (6)C40—N41.478 (5)
C16—H160.93C40—H40A0.97
C17—N101.370 (5)C40—H40B0.97
C17—H170.93N2—Ag22.092 (3)
C18—N91.303 (5)N3—Ag22.090 (4)
C18—N101.327 (5)N5—H5A0.84 (3)
C18—H180.93N5—H5B0.81 (6)
C19—N101.475 (4)N6—H6A0.83 (3)
C19—C20i1.508 (6)N6—H6B0.80 (3)
C19—H19A0.97N8—Ag12.103 (3)
C19—H19B0.97N9—Ag12.100 (3)
C20—C211.387 (6)O1—S11.430 (3)
C20—C251.394 (5)O2—S11.443 (4)
C20—C19i1.508 (6)O1W—H1A0.80 (6)
C21—C221.356 (8)O1W—H1B0.83 (7)
C21—H210.93O3—S11.450 (3)
C22—C231.369 (8)O2W—H2A0.81 (6)
C22—H220.93O2W—H2B0.83 (3)
C23—C241.395 (7)O4—S21.443 (3)
C23—H230.93O3W—H3A0.82 (7)
C24—C251.381 (6)O3W—H3B0.83 (3)
C24—H240.93O5—S21.451 (3)
C25—C261.502 (5)O4W—H4A0.84 (10)
C26—N71.476 (4)O4W—H4B0.87 (8)
C26—H26A0.97O6—S21.449 (3)
C2—C1—C6117.7 (3)N3—C29—N4111.7 (4)
C2—C1—S2118.7 (2)N3—C29—H29124.1
C6—C1—S2123.6 (2)N4—C29—H29124.1
C3—C2—C1121.0 (3)C31—C30—N2110.0 (4)
C3—C2—H2119.5C31—C30—H30125.0
C1—C2—H2119.5N2—C30—H30125.0
C2—C3—C4121.5 (3)C30—C31—N1105.9 (4)
C2—C3—Cl2119.2 (3)C30—C31—H31127.1
C4—C3—Cl2119.3 (3)N1—C31—H31127.1
N6—C4—C5121.0 (3)N2—C32—N1110.6 (4)
N6—C4—C3122.0 (3)N2—C32—H32124.7
C5—C4—C3117.1 (3)N1—C32—H32124.7
C6—C5—C4121.2 (3)N1—C33—C34ii112.0 (3)
C6—C5—H5119.4N1—C33—H33A109.2
C4—C5—H5119.4C34ii—C33—H33A109.2
C5—C6—C1121.6 (3)N1—C33—H33B109.2
C5—C6—Cl1117.6 (2)C34ii—C33—H33B109.2
C1—C6—Cl1120.8 (3)H33A—C33—H33B107.9
C8—C7—C12117.2 (3)C39—C34—C35118.6 (4)
C8—C7—S1125.6 (3)C39—C34—C33ii122.9 (4)
C12—C7—S1117.1 (3)C35—C34—C33ii118.5 (4)
C7—C8—C9122.4 (4)C36—C35—C34121.9 (4)
C7—C8—Cl3121.2 (3)C36—C35—H35119.1
C9—C8—Cl3116.4 (3)C34—C35—H35119.1
C8—C9—C10121.0 (4)C35—C36—C37119.5 (5)
C8—C9—H9119.5C35—C36—H36120.2
C10—C9—H9119.5C37—C36—H36120.2
N5—C10—C11122.6 (4)C36—C37—C38120.5 (5)
N5—C10—C9120.5 (4)C36—C37—H37119.7
C11—C10—C9116.9 (3)C38—C37—H37119.7
C10—C11—C12121.7 (4)C37—C38—C39120.3 (4)
C10—C11—Cl4119.6 (3)C37—C38—H38119.8
C12—C11—Cl4118.6 (3)C39—C38—H38119.8
C11—C12—C7120.8 (4)C38—C39—C34119.1 (4)
C11—C12—H12119.6C38—C39—C40118.3 (4)
C7—C12—H12119.6C34—C39—C40122.6 (4)
N8—C13—N7111.7 (3)N4—C40—C39112.6 (3)
N8—C13—H13124.2N4—C40—H40A109.1
N7—C13—H13124.2C39—C40—H40A109.1
C15—C14—N8110.5 (4)N4—C40—H40B109.1
C15—C14—H14124.8C39—C40—H40B109.1
N8—C14—H14124.8H40A—C40—H40B107.8
C14—C15—N7105.4 (4)C32—N1—C31107.6 (3)
C14—C15—H15127.3C32—N1—C33125.1 (4)
N7—C15—H15127.3C31—N1—C33127.3 (4)
C17—C16—N9110.0 (4)C32—N2—C30105.9 (3)
C17—C16—H16125.0C32—N2—Ag2128.8 (3)
N9—C16—H16125.0C30—N2—Ag2125.3 (3)
C16—C17—N10105.4 (4)C29—N3—C27104.9 (4)
C16—C17—H17127.3C29—N3—Ag2124.5 (3)
N10—C17—H17127.3C27—N3—Ag2130.6 (3)
N9—C18—N10111.9 (4)C29—N4—C28107.8 (3)
N9—C18—H18124.0C29—N4—C40125.9 (4)
N10—C18—H18124.0C28—N4—C40126.2 (4)
N10—C19—C20i112.7 (3)C10—N5—H5A112 (4)
N10—C19—H19A109.1C10—N5—H5B113 (4)
C20i—C19—H19A109.1H5A—N5—H5B126 (5)
N10—C19—H19B109.1C4—N6—H6A124 (5)
C20i—C19—H19B109.1C4—N6—H6B120 (5)
H19A—C19—H19B107.8H6A—N6—H6B113 (6)
C21—C20—C25118.5 (4)C13—N7—C15107.5 (3)
C21—C20—C19i118.8 (4)C13—N7—C26126.3 (3)
C25—C20—C19i122.7 (4)C15—N7—C26126.1 (4)
C22—C21—C20121.5 (4)C13—N8—C14104.8 (3)
C22—C21—H21119.3C13—N8—Ag1125.4 (3)
C20—C21—H21119.3C14—N8—Ag1129.8 (3)
C21—C22—C23120.5 (5)C18—N9—C16105.3 (3)
C21—C22—H22119.7C18—N9—Ag1128.8 (3)
C23—C22—H22119.7C16—N9—Ag1125.8 (3)
C22—C23—C24119.5 (5)C18—N10—C17107.4 (3)
C22—C23—H23120.3C18—N10—C19125.5 (4)
C24—C23—H23120.3C17—N10—C19127.1 (4)
C25—C24—C23120.2 (4)H1A—O1W—H1B104 (5)
C25—C24—H24119.9H2A—O2W—H2B104 (6)
C23—C24—H24119.9H3A—O3W—H3B105 (4)
C24—C25—C20119.9 (4)H4A—O4W—H4B101 (4)
C24—C25—C26118.0 (3)O1—S1—O2113.8 (2)
C20—C25—C26122.1 (4)O1—S1—O3112.0 (2)
N7—C26—C25112.3 (3)O2—S1—O3111.8 (2)
N7—C26—H26A109.1O1—S1—C7108.49 (17)
C25—C26—H26A109.1O2—S1—C7104.3 (2)
N7—C26—H26B109.1O3—S1—C7105.73 (18)
C25—C26—H26B109.1O4—S2—O6112.7 (2)
H26A—C26—H26B107.9O4—S2—O5113.29 (19)
C28—C27—N3110.4 (4)O6—S2—O5111.49 (18)
C28—C27—H27124.8O4—S2—C1105.88 (18)
N3—C27—H27124.8O6—S2—C1107.38 (17)
C27—C28—N4105.2 (4)O5—S2—C1105.46 (16)
C27—C28—H28127.4N9—Ag1—N8175.91 (13)
N4—C28—H28127.4N3—Ag2—N2178.95 (15)
C6—C1—C2—C31.0 (5)C33ii—C34—C39—C38−179.2 (3)
S2—C1—C2—C3−179.5 (3)C35—C34—C39—C40179.1 (4)
C1—C2—C3—C4−1.5 (5)C33ii—C34—C39—C400.5 (5)
C1—C2—C3—Cl2179.6 (3)C38—C39—C40—N4−95.9 (4)
C2—C3—C4—N6−179.4 (4)C34—C39—C40—N484.4 (5)
Cl2—C3—C4—N6−0.5 (6)N2—C32—N1—C31−0.5 (5)
C2—C3—C4—C50.9 (5)N2—C32—N1—C33−178.8 (3)
Cl2—C3—C4—C5179.8 (3)C30—C31—N1—C320.6 (5)
N6—C4—C5—C6−179.6 (4)C30—C31—N1—C33178.9 (4)
C3—C4—C5—C60.1 (5)C34ii—C33—N1—C32−145.3 (4)
C4—C5—C6—C1−0.6 (5)C34ii—C33—N1—C3136.7 (6)
C4—C5—C6—Cl1178.6 (3)N1—C32—N2—C300.2 (5)
C2—C1—C6—C50.0 (5)N1—C32—N2—Ag2−177.8 (2)
S2—C1—C6—C5−179.4 (3)C31—C30—N2—C320.2 (5)
C2—C1—C6—Cl1−179.1 (2)C31—C30—N2—Ag2178.3 (3)
S2—C1—C6—Cl11.5 (4)N4—C29—N3—C270.6 (5)
C12—C7—C8—C9−1.1 (5)N4—C29—N3—Ag2178.8 (3)
S1—C7—C8—C9−176.0 (3)C28—C27—N3—C29−0.6 (5)
C12—C7—C8—Cl3179.4 (3)C28—C27—N3—Ag2−178.6 (3)
S1—C7—C8—Cl34.5 (5)N3—C29—N4—C28−0.4 (5)
C7—C8—C9—C101.6 (6)N3—C29—N4—C40−176.5 (3)
Cl3—C8—C9—C10−178.9 (3)C27—C28—N4—C290.0 (5)
C8—C9—C10—N5176.3 (4)C27—C28—N4—C40176.1 (4)
C8—C9—C10—C11−1.3 (6)C39—C40—N4—C29−135.6 (4)
N5—C10—C11—C12−177.1 (4)C39—C40—N4—C2849.0 (6)
C9—C10—C11—C120.5 (5)N8—C13—N7—C151.5 (4)
N5—C10—C11—Cl42.0 (5)N8—C13—N7—C26178.6 (3)
C9—C10—C11—Cl4179.6 (3)C14—C15—N7—C13−1.2 (4)
C10—C11—C12—C70.0 (5)C14—C15—N7—C26−178.3 (4)
Cl4—C11—C12—C7−179.1 (3)C25—C26—N7—C13124.6 (4)
C8—C7—C12—C110.3 (5)C25—C26—N7—C15−58.8 (5)
S1—C7—C12—C11175.7 (3)N7—C13—N8—C14−1.2 (5)
N8—C14—C15—N70.5 (5)N7—C13—N8—Ag1179.5 (2)
N9—C16—C17—N100.1 (5)C15—C14—N8—C130.4 (5)
C25—C20—C21—C22−0.2 (6)C15—C14—N8—Ag1179.7 (3)
C19i—C20—C21—C22−178.3 (4)N10—C18—N9—C16−0.5 (4)
C20—C21—C22—C230.0 (7)N10—C18—N9—Ag1175.9 (2)
C21—C22—C23—C240.6 (8)C17—C16—N9—C180.2 (5)
C22—C23—C24—C25−0.8 (7)C17—C16—N9—Ag1−176.3 (3)
C23—C24—C25—C200.6 (6)N9—C18—N10—C170.6 (5)
C23—C24—C25—C26179.5 (4)N9—C18—N10—C19178.9 (3)
C21—C20—C25—C24−0.1 (5)C16—C17—N10—C18−0.4 (5)
C19i—C20—C25—C24177.9 (3)C16—C17—N10—C19−178.7 (4)
C21—C20—C25—C26−179.0 (3)C20i—C19—N10—C18157.7 (4)
C19i—C20—C25—C26−1.0 (5)C20i—C19—N10—C17−24.3 (6)
C24—C25—C26—N7104.5 (4)C8—C7—S1—O1−49.1 (4)
C20—C25—C26—N7−76.6 (4)C12—C7—S1—O1135.9 (3)
N3—C27—C28—N40.4 (5)C8—C7—S1—O2−170.8 (3)
N2—C30—C31—N1−0.5 (5)C12—C7—S1—O214.2 (3)
C39—C34—C35—C36−0.1 (6)C8—C7—S1—O371.2 (4)
C33ii—C34—C35—C36178.5 (4)C12—C7—S1—O3−103.8 (3)
C34—C35—C36—C371.0 (7)C2—C1—S2—O4115.0 (3)
C35—C36—C37—C38−1.0 (8)C6—C1—S2—O4−65.6 (3)
C36—C37—C38—C390.3 (7)C2—C1—S2—O6−124.4 (3)
C37—C38—C39—C340.5 (6)C6—C1—S2—O655.1 (3)
C37—C38—C39—C40−179.2 (4)C2—C1—S2—O5−5.4 (3)
C35—C34—C39—C38−0.6 (5)C6—C1—S2—O5174.1 (3)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2W—H2A···O60.81 (6)2.15 (7)2.868 (5)148 (7)
O3W—H3A···O20.82 (7)2.00 (7)2.819 (6)172 (9)
O1W—H1A···O4iii0.80 (6)1.99 (6)2.762 (5)165 (7)
N6—H6B···O2iv0.80 (3)2.19 (4)2.928 (5)154 (6)
N5—H5B···O5v0.81 (6)2.28 (6)2.913 (5)136 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2638).

References

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  • Li, F.-F., Ma, J.-F., Song, S.-Y., Yang, J., Jia, H.-Q. & Hu, N.-H. (2006). Cryst. Growth Des.6, 209–215.
  • Liu, H.-Y., Wu, H., Ma, J.-F., Song, S.-Y., Yang, J., Liu, Y.-Y. & Su, Z.-M. (2007). Inorg. Chem.46, 7299–7311. [PubMed]
  • Ma, J.-F., Yang, J., Li, S.-L., Song, S.-Y., Zhang, H.-J., Wang, H.-S. & Yang, K.-Y. (2005). Cryst. Growth Des.5, 807–812.
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