metal-organic compounds
Bis[μ-1,2-bis(1H-imidazol-1-ylmethyl)benzene-κ2N3:N3′]disilver(I) bis(4-amino-2,5-dichlorobenzenesulfonate) tetrahydrate
aDepartment of Chemistry and Pharmaceutical Engineering, Suihua University, Suihua 152061, People's Republic of China
*Correspondence e-mail: lhy4486@yahoo.com.cn
The 2(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 intermolecular O—H⋯O and N—H⋯O hydrogen bonds form a three-dimensional network.
of the title compound, [AgRelated literature
For related literature, see: Aakeröy & Beatty (1998); Cote & Shimizu (2004); Feazell et al. (2006); Li et al. (2006); Liu et al. (2007); Ma et al. (2005).
Experimental
Crystal data
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Refinement
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: PROCESS-AUTO; 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.
Supporting information
10.1107/S1600536808023052/ci2638sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808023052/ci2638Isup2.hkl
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.
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.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
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).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. |
[Ag2(C14H14N4)2](C6H4Cl2NO3S)2·4H2O | Z = 2 |
Mr = 1246.51 | F(000) = 1256 |
Triclinic, P1 | Dx = 1.712 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 11.732 (6) Å | Cell parameters from 10576 reflections |
b = 14.598 (6) Å | θ = 3.0–27.5° |
c = 15.718 (6) Å | µ = 1.18 mm−1 |
α = 79.068 (12)° | T = 293 K |
β = 72.843 (19)° | Block, colourless |
γ = 70.991 (17)° | 0.35 × 0.25 × 0.24 mm |
V = 2418.8 (18) Å3 |
Rigaku R-AXIS RAPID diffractometer | 10576 independent reflections |
Radiation source: fine-focus sealed tube | 6897 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→18 |
Tmin = 0.716, Tmax = 0.753 | l = −20→19 |
19762 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0975P)2] where P = (Fo2 + 2Fc2)/3 |
10576 reflections | (Δ/σ)max = 0.002 |
649 parameters | Δρmax = 0.92 e Å−3 |
13 restraints | Δρmin = −0.36 e Å−3 |
[Ag2(C14H14N4)2](C6H4Cl2NO3S)2·4H2O | γ = 70.991 (17)° |
Mr = 1246.51 | V = 2418.8 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.732 (6) Å | Mo Kα radiation |
b = 14.598 (6) Å | µ = 1.18 mm−1 |
c = 15.718 (6) Å | T = 293 K |
α = 79.068 (12)° | 0.35 × 0.25 × 0.24 mm |
β = 72.843 (19)° |
Rigaku R-AXIS RAPID diffractometer | 10576 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6897 reflections with I > 2σ(I) |
Tmin = 0.716, Tmax = 0.753 | Rint = 0.023 |
19762 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 13 restraints |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.92 e Å−3 |
10576 reflections | Δρmin = −0.36 e Å−3 |
649 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8198 (3) | 0.6791 (2) | 0.2186 (2) | 0.0354 (7) | |
C2 | 0.7330 (3) | 0.7577 (2) | 0.1876 (2) | 0.0366 (7) | |
H2 | 0.7202 | 0.7590 | 0.1317 | 0.044* | |
C3 | 0.6652 (3) | 0.8340 (2) | 0.2383 (2) | 0.0388 (7) | |
C4 | 0.6792 (4) | 0.8342 (2) | 0.3238 (2) | 0.0438 (8) | |
C5 | 0.7666 (3) | 0.7540 (2) | 0.3548 (2) | 0.0427 (8) | |
H5 | 0.7784 | 0.7516 | 0.4113 | 0.051* | |
C6 | 0.8349 (3) | 0.6793 (2) | 0.3037 (2) | 0.0356 (7) | |
C7 | 0.3133 (4) | 0.2224 (2) | 0.3052 (2) | 0.0443 (8) | |
C8 | 0.1970 (4) | 0.2875 (2) | 0.3230 (2) | 0.0475 (9) | |
C9 | 0.1282 (4) | 0.3219 (3) | 0.2605 (2) | 0.0480 (9) | |
H9 | 0.0505 | 0.3674 | 0.2751 | 0.058* | |
C10 | 0.1729 (4) | 0.2898 (3) | 0.1759 (2) | 0.0474 (9) | |
C11 | 0.2901 (4) | 0.2236 (2) | 0.1576 (2) | 0.0470 (9) | |
C12 | 0.3595 (4) | 0.1902 (2) | 0.2207 (3) | 0.0458 (8) | |
H12 | 0.4380 | 0.1457 | 0.2062 | 0.055* | |
C13 | 0.4409 (4) | 0.3953 (3) | 0.8315 (3) | 0.0484 (9) | |
H13 | 0.3734 | 0.4511 | 0.8355 | 0.058* | |
C14 | 0.5857 (4) | 0.2737 (3) | 0.8637 (3) | 0.0601 (11) | |
H14 | 0.6393 | 0.2289 | 0.8953 | 0.072* | |
C15 | 0.5879 (4) | 0.2697 (3) | 0.7782 (3) | 0.0538 (10) | |
H15 | 0.6413 | 0.2227 | 0.7406 | 0.065* | |
C16 | 0.2850 (4) | 0.5007 (3) | 1.1974 (3) | 0.0592 (11) | |
H16 | 0.2168 | 0.5300 | 1.1731 | 0.071* | |
C17 | 0.2902 (4) | 0.5130 (3) | 1.2789 (3) | 0.0562 (10) | |
H17 | 0.2282 | 0.5513 | 1.3207 | 0.067* | |
C18 | 0.4640 (4) | 0.4143 (3) | 1.2125 (3) | 0.0525 (9) | |
H18 | 0.5443 | 0.3719 | 1.2019 | 0.063* | |
C19 | 0.4582 (5) | 0.4438 (3) | 1.3650 (3) | 0.0597 (12) | |
H19A | 0.5467 | 0.4372 | 1.3440 | 0.072* | |
H19B | 0.4481 | 0.3839 | 1.4012 | 0.072* | |
C20 | 0.6035 (4) | 0.4727 (3) | 0.5778 (2) | 0.0473 (9) | |
C21 | 0.7006 (5) | 0.4807 (4) | 0.5034 (3) | 0.0672 (13) | |
H21 | 0.7272 | 0.5363 | 0.4912 | 0.081* | |
C22 | 0.7575 (5) | 0.4091 (5) | 0.4482 (3) | 0.0814 (17) | |
H22 | 0.8223 | 0.4163 | 0.3988 | 0.098* | |
C23 | 0.7203 (5) | 0.3264 (5) | 0.4645 (3) | 0.0805 (16) | |
H23 | 0.7600 | 0.2772 | 0.4268 | 0.097* | |
C24 | 0.6223 (5) | 0.3165 (3) | 0.5383 (3) | 0.0597 (11) | |
H24 | 0.5958 | 0.2609 | 0.5494 | 0.072* | |
C25 | 0.5645 (4) | 0.3890 (3) | 0.5949 (2) | 0.0426 (8) | |
C26 | 0.4588 (4) | 0.3750 (3) | 0.6729 (2) | 0.0513 (9) | |
H26A | 0.3906 | 0.4347 | 0.6767 | 0.062* | |
H26B | 0.4293 | 0.3241 | 0.6629 | 0.062* | |
C27 | 0.9272 (5) | 0.2163 (3) | 0.6345 (3) | 0.0624 (11) | |
H27 | 0.8772 | 0.2668 | 0.6042 | 0.075* | |
C28 | 0.9248 (4) | 0.2116 (3) | 0.7213 (3) | 0.0602 (11) | |
H28 | 0.8742 | 0.2564 | 0.7616 | 0.072* | |
C29 | 1.0624 (4) | 0.0856 (3) | 0.6622 (3) | 0.0555 (10) | |
H29 | 1.1252 | 0.0270 | 0.6561 | 0.067* | |
C30 | 1.2267 (4) | −0.0007 (3) | 0.2968 (3) | 0.0548 (10) | |
H30 | 1.2907 | −0.0338 | 0.3246 | 0.066* | |
C31 | 1.2282 (4) | −0.0092 (3) | 0.2127 (3) | 0.0529 (9) | |
H31 | 1.2920 | −0.0478 | 0.1721 | 0.064* | |
C32 | 1.0534 (4) | 0.0933 (3) | 0.2743 (3) | 0.0556 (10) | |
H32 | 0.9746 | 0.1379 | 0.2823 | 0.067* | |
C33 | 1.0740 (5) | 0.0685 (3) | 0.1172 (3) | 0.0587 (11) | |
H33A | 1.1058 | 0.1188 | 0.0771 | 0.070* | |
H33B | 0.9837 | 0.0920 | 0.1323 | 0.070* | |
C34 | 0.8843 (4) | 0.0216 (3) | 0.9298 (2) | 0.0479 (9) | |
C35 | 0.7849 (5) | 0.0306 (4) | 1.0058 (3) | 0.0628 (12) | |
H35 | 0.7457 | −0.0184 | 1.0247 | 0.075* | |
C36 | 0.7438 (5) | 0.1089 (4) | 1.0529 (3) | 0.0759 (14) | |
H36 | 0.6781 | 0.1127 | 1.1039 | 0.091* | |
C37 | 0.7994 (6) | 0.1817 (4) | 1.0251 (3) | 0.0802 (15) | |
H37 | 0.7705 | 0.2360 | 1.0567 | 0.096* | |
C38 | 0.8985 (5) | 0.1757 (4) | 0.9501 (3) | 0.0682 (13) | |
H38 | 0.9360 | 0.2257 | 0.9318 | 0.082* | |
C39 | 0.9421 (4) | 0.0953 (3) | 0.9020 (2) | 0.0525 (10) | |
C40 | 1.0505 (4) | 0.0916 (4) | 0.8221 (3) | 0.0634 (12) | |
H40A | 1.0991 | 0.1308 | 0.8293 | 0.076* | |
H40B | 1.1034 | 0.0249 | 0.8190 | 0.076* | |
N1 | 1.1171 (3) | 0.0505 (2) | 0.1992 (2) | 0.0470 (7) | |
N2 | 1.1180 (4) | 0.0633 (3) | 0.3353 (2) | 0.0544 (8) | |
N3 | 1.0130 (4) | 0.1370 (3) | 0.5975 (2) | 0.0584 (9) | |
N4 | 1.0121 (3) | 0.1272 (2) | 0.7374 (2) | 0.0509 (8) | |
N5 | 0.1005 (4) | 0.3204 (3) | 0.1159 (3) | 0.0668 (11) | |
H5A | 0.041 (4) | 0.371 (3) | 0.130 (4) | 0.100* | |
H5B | 0.140 (6) | 0.309 (4) | 0.066 (4) | 0.100* | |
N6 | 0.6122 (5) | 0.9084 (3) | 0.3745 (3) | 0.0742 (13) | |
H6A | 0.622 (6) | 0.912 (4) | 0.424 (3) | 0.111* | |
H6B | 0.580 (6) | 0.960 (3) | 0.351 (4) | 0.111* | |
N7 | 0.4956 (3) | 0.3487 (2) | 0.75842 (19) | 0.0425 (7) | |
N8 | 0.4938 (3) | 0.3527 (2) | 0.8973 (2) | 0.0516 (8) | |
N9 | 0.3948 (3) | 0.4387 (2) | 1.1558 (2) | 0.0516 (8) | |
N10 | 0.4063 (3) | 0.4572 (2) | 1.2871 (2) | 0.0457 (7) | |
O1 | 0.4075 (4) | 0.2441 (2) | 0.4284 (2) | 0.0799 (11) | |
O2 | 0.5249 (3) | 0.1193 (2) | 0.3297 (2) | 0.0792 (10) | |
O1W | 0.2170 (4) | 0.5412 (3) | 0.9721 (2) | 0.0832 (11) | |
H1A | 0.169 (7) | 0.563 (5) | 1.016 (4) | 0.125* | |
H1B | 0.178 (6) | 0.515 (4) | 0.953 (4) | 0.125* | |
O3 | 0.3444 (3) | 0.1006 (2) | 0.4441 (2) | 0.0727 (10) | |
O2W | 0.7688 (5) | 0.3506 (4) | 0.1994 (4) | 0.1072 (15) | |
H2A | 0.810 (8) | 0.375 (6) | 0.216 (5) | 0.161* | |
H2B | 0.794 (8) | 0.356 (6) | 0.144 (2) | 0.161* | |
O4 | 1.0322 (3) | 0.5854 (3) | 0.1273 (2) | 0.0742 (9) | |
O3W | 0.7592 (4) | 0.1554 (4) | 0.2732 (4) | 0.1118 (16) | |
H3A | 0.691 (5) | 0.145 (5) | 0.285 (6) | 0.168* | |
H3B | 0.746 (7) | 0.214 (3) | 0.254 (5) | 0.168* | |
O5 | 0.8507 (3) | 0.6085 (2) | 0.07362 (17) | 0.0578 (7) | |
O4W | 0.2819 (6) | 0.9250 (4) | 0.5166 (4) | 0.1301 (19) | |
H4A | 0.299 (8) | 0.963 (6) | 0.542 (6) | 0.195* | |
H4B | 0.354 (5) | 0.902 (7) | 0.480 (5) | 0.195* | |
O6 | 0.8852 (3) | 0.49480 (18) | 0.2017 (2) | 0.0645 (8) | |
S1 | 0.40489 (11) | 0.16866 (7) | 0.38332 (8) | 0.0534 (3) | |
S2 | 0.90401 (9) | 0.58453 (7) | 0.15024 (6) | 0.0444 (2) | |
Ag1 | 0.44041 (4) | 0.40061 (3) | 1.02509 (2) | 0.06083 (13) | |
Ag2 | 1.06711 (4) | 0.09945 (3) | 0.46655 (2) | 0.06964 (14) | |
Cl1 | 0.94358 (9) | 0.58423 (6) | 0.34728 (6) | 0.0462 (2) | |
Cl2 | 0.55802 (10) | 0.93124 (7) | 0.19615 (7) | 0.0550 (3) | |
Cl3 | 0.12837 (12) | 0.33250 (8) | 0.42796 (7) | 0.0687 (3) | |
Cl4 | 0.35254 (12) | 0.17913 (8) | 0.05280 (7) | 0.0663 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0315 (18) | 0.0399 (16) | 0.0357 (15) | −0.0105 (14) | −0.0085 (13) | −0.0052 (14) |
C2 | 0.0325 (18) | 0.0433 (17) | 0.0334 (15) | −0.0118 (14) | −0.0083 (13) | −0.0006 (14) |
C3 | 0.0345 (19) | 0.0360 (16) | 0.0422 (17) | −0.0089 (14) | −0.0091 (14) | 0.0014 (15) |
C4 | 0.049 (2) | 0.0370 (16) | 0.0439 (18) | −0.0071 (15) | −0.0124 (16) | −0.0087 (15) |
C5 | 0.048 (2) | 0.0433 (17) | 0.0387 (17) | −0.0096 (16) | −0.0154 (16) | −0.0070 (15) |
C6 | 0.0338 (18) | 0.0354 (15) | 0.0388 (16) | −0.0109 (13) | −0.0118 (14) | −0.0005 (14) |
C7 | 0.054 (2) | 0.0309 (15) | 0.049 (2) | −0.0136 (15) | −0.0180 (17) | 0.0035 (15) |
C8 | 0.057 (2) | 0.0329 (16) | 0.0454 (19) | −0.0040 (16) | −0.0121 (17) | −0.0037 (15) |
C9 | 0.052 (2) | 0.0379 (17) | 0.0407 (18) | 0.0017 (16) | −0.0082 (17) | −0.0048 (15) |
C10 | 0.055 (2) | 0.0391 (17) | 0.0422 (18) | −0.0104 (17) | −0.0107 (17) | 0.0027 (16) |
C11 | 0.059 (3) | 0.0356 (16) | 0.0442 (19) | −0.0200 (17) | −0.0040 (17) | −0.0021 (15) |
C12 | 0.046 (2) | 0.0318 (16) | 0.053 (2) | −0.0083 (15) | −0.0046 (17) | −0.0069 (16) |
C13 | 0.042 (2) | 0.0469 (19) | 0.048 (2) | −0.0110 (16) | −0.0016 (17) | −0.0048 (17) |
C14 | 0.064 (3) | 0.058 (2) | 0.048 (2) | −0.006 (2) | −0.017 (2) | 0.0007 (19) |
C15 | 0.058 (3) | 0.049 (2) | 0.0436 (19) | −0.0066 (18) | −0.0071 (18) | −0.0067 (17) |
C16 | 0.053 (3) | 0.080 (3) | 0.055 (2) | −0.019 (2) | −0.022 (2) | −0.017 (2) |
C17 | 0.048 (2) | 0.076 (3) | 0.052 (2) | −0.018 (2) | −0.0129 (19) | −0.022 (2) |
C18 | 0.056 (3) | 0.050 (2) | 0.057 (2) | −0.0168 (19) | −0.019 (2) | −0.0073 (19) |
C19 | 0.088 (3) | 0.047 (2) | 0.060 (2) | −0.021 (2) | −0.043 (2) | 0.0001 (19) |
C20 | 0.059 (3) | 0.057 (2) | 0.0376 (17) | −0.0276 (19) | −0.0206 (17) | 0.0026 (17) |
C21 | 0.079 (3) | 0.100 (3) | 0.041 (2) | −0.059 (3) | −0.018 (2) | 0.011 (2) |
C22 | 0.065 (3) | 0.144 (5) | 0.043 (2) | −0.049 (4) | −0.009 (2) | −0.001 (3) |
C23 | 0.081 (4) | 0.110 (4) | 0.047 (2) | −0.012 (3) | −0.015 (2) | −0.030 (3) |
C24 | 0.073 (3) | 0.060 (2) | 0.051 (2) | −0.020 (2) | −0.017 (2) | −0.013 (2) |
C25 | 0.048 (2) | 0.0498 (19) | 0.0366 (16) | −0.0219 (17) | −0.0159 (16) | 0.0032 (16) |
C26 | 0.051 (2) | 0.064 (2) | 0.0449 (19) | −0.026 (2) | −0.0159 (18) | 0.0026 (18) |
C27 | 0.075 (3) | 0.061 (2) | 0.049 (2) | −0.020 (2) | −0.017 (2) | 0.004 (2) |
C28 | 0.063 (3) | 0.064 (3) | 0.047 (2) | −0.020 (2) | −0.005 (2) | −0.001 (2) |
C29 | 0.054 (3) | 0.058 (2) | 0.053 (2) | −0.020 (2) | −0.0076 (19) | −0.004 (2) |
C30 | 0.056 (3) | 0.056 (2) | 0.055 (2) | −0.0096 (19) | −0.022 (2) | −0.0115 (19) |
C31 | 0.051 (3) | 0.057 (2) | 0.053 (2) | −0.0085 (19) | −0.0183 (19) | −0.0155 (18) |
C32 | 0.050 (3) | 0.062 (2) | 0.058 (2) | −0.017 (2) | −0.015 (2) | −0.013 (2) |
C33 | 0.074 (3) | 0.057 (2) | 0.054 (2) | −0.021 (2) | −0.033 (2) | 0.0028 (19) |
C34 | 0.049 (2) | 0.064 (2) | 0.0389 (17) | −0.0257 (19) | −0.0177 (17) | 0.0020 (17) |
C35 | 0.064 (3) | 0.086 (3) | 0.047 (2) | −0.035 (3) | −0.016 (2) | 0.002 (2) |
C36 | 0.071 (4) | 0.108 (4) | 0.047 (2) | −0.024 (3) | −0.010 (2) | −0.013 (3) |
C37 | 0.102 (5) | 0.089 (4) | 0.058 (3) | −0.020 (3) | −0.031 (3) | −0.025 (3) |
C38 | 0.089 (4) | 0.076 (3) | 0.060 (3) | −0.042 (3) | −0.034 (3) | 0.002 (2) |
C39 | 0.060 (3) | 0.069 (2) | 0.0423 (19) | −0.031 (2) | −0.0258 (18) | 0.0057 (19) |
C40 | 0.054 (3) | 0.096 (3) | 0.051 (2) | −0.039 (2) | −0.017 (2) | 0.006 (2) |
N1 | 0.052 (2) | 0.0457 (16) | 0.0515 (17) | −0.0198 (15) | −0.0194 (15) | −0.0032 (14) |
N2 | 0.062 (2) | 0.060 (2) | 0.0488 (18) | −0.0249 (18) | −0.0172 (17) | −0.0071 (16) |
N3 | 0.070 (3) | 0.0564 (19) | 0.0496 (19) | −0.0232 (18) | −0.0090 (17) | −0.0071 (17) |
N4 | 0.050 (2) | 0.0619 (19) | 0.0448 (17) | −0.0266 (17) | −0.0124 (15) | 0.0048 (16) |
N5 | 0.071 (3) | 0.068 (2) | 0.0485 (19) | 0.001 (2) | −0.023 (2) | −0.0029 (19) |
N6 | 0.100 (3) | 0.0504 (19) | 0.061 (2) | 0.016 (2) | −0.036 (2) | −0.0224 (18) |
N7 | 0.0403 (18) | 0.0440 (15) | 0.0406 (15) | −0.0167 (13) | −0.0046 (13) | 0.0010 (13) |
N8 | 0.058 (2) | 0.0554 (18) | 0.0439 (16) | −0.0223 (16) | −0.0093 (15) | −0.0044 (15) |
N9 | 0.058 (2) | 0.0583 (19) | 0.0448 (17) | −0.0223 (17) | −0.0136 (16) | −0.0088 (15) |
N10 | 0.055 (2) | 0.0435 (15) | 0.0468 (16) | −0.0206 (15) | −0.0211 (15) | −0.0006 (14) |
O1 | 0.116 (3) | 0.0512 (16) | 0.099 (2) | −0.0303 (18) | −0.061 (2) | −0.0044 (17) |
O2 | 0.059 (2) | 0.0723 (19) | 0.103 (3) | −0.0016 (17) | −0.033 (2) | −0.0103 (19) |
O1W | 0.067 (3) | 0.118 (3) | 0.067 (2) | −0.034 (2) | 0.0094 (17) | −0.043 (2) |
O3 | 0.098 (3) | 0.0560 (16) | 0.077 (2) | −0.0340 (17) | −0.046 (2) | 0.0235 (16) |
O2W | 0.092 (3) | 0.108 (3) | 0.131 (4) | −0.050 (3) | −0.020 (3) | −0.010 (3) |
O4 | 0.0386 (18) | 0.113 (3) | 0.0653 (18) | −0.0073 (17) | −0.0007 (14) | −0.0401 (18) |
O3W | 0.069 (3) | 0.094 (3) | 0.165 (5) | −0.008 (2) | −0.041 (3) | −0.005 (3) |
O5 | 0.067 (2) | 0.0644 (16) | 0.0407 (13) | −0.0052 (14) | −0.0208 (13) | −0.0158 (12) |
O4W | 0.188 (6) | 0.085 (3) | 0.127 (4) | −0.043 (4) | −0.051 (4) | −0.010 (3) |
O6 | 0.095 (2) | 0.0394 (13) | 0.0644 (17) | −0.0098 (14) | −0.0358 (17) | −0.0090 (13) |
S1 | 0.0593 (7) | 0.0375 (4) | 0.0692 (6) | −0.0130 (4) | −0.0298 (5) | 0.0011 (4) |
S2 | 0.0410 (5) | 0.0485 (5) | 0.0396 (4) | −0.0005 (4) | −0.0116 (4) | −0.0141 (4) |
Ag1 | 0.0758 (3) | 0.0704 (2) | 0.04346 (17) | −0.03161 (18) | −0.00942 (15) | −0.01273 (15) |
Ag2 | 0.0871 (3) | 0.0778 (2) | 0.04749 (19) | −0.0295 (2) | −0.01030 (17) | −0.01494 (17) |
Cl1 | 0.0453 (5) | 0.0444 (4) | 0.0475 (5) | −0.0044 (4) | −0.0209 (4) | −0.0021 (4) |
Cl2 | 0.0497 (6) | 0.0453 (5) | 0.0618 (6) | 0.0019 (4) | −0.0213 (5) | −0.0022 (4) |
Cl3 | 0.0803 (8) | 0.0638 (6) | 0.0436 (5) | 0.0058 (5) | −0.0142 (5) | −0.0120 (5) |
Cl4 | 0.0791 (8) | 0.0626 (6) | 0.0467 (5) | −0.0158 (6) | 0.0014 (5) | −0.0164 (5) |
C1—C2 | 1.382 (4) | C26—H26B | 0.97 |
C1—C6 | 1.401 (4) | C27—C28 | 1.345 (6) |
C1—S2 | 1.756 (3) | C27—N3 | 1.357 (6) |
C2—C3 | 1.377 (5) | C27—H27 | 0.93 |
C2—H2 | 0.93 | C28—N4 | 1.358 (6) |
C3—C4 | 1.402 (5) | C28—H28 | 0.93 |
C3—Cl2 | 1.734 (3) | C29—N3 | 1.308 (5) |
C4—N6 | 1.353 (5) | C29—N4 | 1.319 (5) |
C4—C5 | 1.398 (5) | C29—H29 | 0.93 |
C5—C6 | 1.364 (5) | C30—C31 | 1.346 (6) |
C5—H5 | 0.93 | C30—N2 | 1.360 (6) |
C6—Cl1 | 1.738 (3) | C30—H30 | 0.93 |
C7—C8 | 1.369 (5) | C31—N1 | 1.363 (5) |
C7—C12 | 1.387 (5) | C31—H31 | 0.93 |
C7—S1 | 1.773 (4) | C32—N2 | 1.317 (5) |
C8—C9 | 1.373 (5) | C32—N1 | 1.341 (5) |
C8—Cl3 | 1.756 (4) | C32—H32 | 0.93 |
C9—C10 | 1.388 (5) | C33—N1 | 1.468 (5) |
C9—H9 | 0.93 | C33—C34ii | 1.499 (6) |
C10—N5 | 1.371 (5) | C33—H33A | 0.97 |
C10—C11 | 1.383 (6) | C33—H33B | 0.97 |
C11—C12 | 1.385 (5) | C34—C39 | 1.390 (5) |
C11—Cl4 | 1.748 (4) | C34—C35 | 1.393 (6) |
C12—H12 | 0.93 | C34—C33ii | 1.499 (6) |
C13—N8 | 1.313 (5) | C35—C36 | 1.355 (7) |
C13—N7 | 1.331 (5) | C35—H35 | 0.93 |
C13—H13 | 0.93 | C36—C37 | 1.362 (8) |
C14—C15 | 1.350 (6) | C36—H36 | 0.93 |
C14—N8 | 1.362 (6) | C37—C38 | 1.383 (8) |
C14—H14 | 0.93 | C37—H37 | 0.93 |
C15—N7 | 1.359 (5) | C38—C39 | 1.388 (7) |
C15—H15 | 0.93 | C38—H38 | 0.93 |
C16—C17 | 1.349 (6) | C39—C40 | 1.495 (6) |
C16—N9 | 1.369 (6) | C40—N4 | 1.478 (5) |
C16—H16 | 0.93 | C40—H40A | 0.97 |
C17—N10 | 1.370 (5) | C40—H40B | 0.97 |
C17—H17 | 0.93 | N2—Ag2 | 2.092 (3) |
C18—N9 | 1.303 (5) | N3—Ag2 | 2.090 (4) |
C18—N10 | 1.327 (5) | N5—H5A | 0.84 (3) |
C18—H18 | 0.93 | N5—H5B | 0.81 (6) |
C19—N10 | 1.475 (4) | N6—H6A | 0.83 (3) |
C19—C20i | 1.508 (6) | N6—H6B | 0.80 (3) |
C19—H19A | 0.97 | N8—Ag1 | 2.103 (3) |
C19—H19B | 0.97 | N9—Ag1 | 2.100 (3) |
C20—C21 | 1.387 (6) | O1—S1 | 1.430 (3) |
C20—C25 | 1.394 (5) | O2—S1 | 1.443 (4) |
C20—C19i | 1.508 (6) | O1W—H1A | 0.80 (6) |
C21—C22 | 1.356 (8) | O1W—H1B | 0.83 (7) |
C21—H21 | 0.93 | O3—S1 | 1.450 (3) |
C22—C23 | 1.369 (8) | O2W—H2A | 0.81 (6) |
C22—H22 | 0.93 | O2W—H2B | 0.83 (3) |
C23—C24 | 1.395 (7) | O4—S2 | 1.443 (3) |
C23—H23 | 0.93 | O3W—H3A | 0.82 (7) |
C24—C25 | 1.381 (6) | O3W—H3B | 0.83 (3) |
C24—H24 | 0.93 | O5—S2 | 1.451 (3) |
C25—C26 | 1.502 (5) | O4W—H4A | 0.84 (10) |
C26—N7 | 1.476 (4) | O4W—H4B | 0.87 (8) |
C26—H26A | 0.97 | O6—S2 | 1.449 (3) |
C2—C1—C6 | 117.7 (3) | N3—C29—N4 | 111.7 (4) |
C2—C1—S2 | 118.7 (2) | N3—C29—H29 | 124.1 |
C6—C1—S2 | 123.6 (2) | N4—C29—H29 | 124.1 |
C3—C2—C1 | 121.0 (3) | C31—C30—N2 | 110.0 (4) |
C3—C2—H2 | 119.5 | C31—C30—H30 | 125.0 |
C1—C2—H2 | 119.5 | N2—C30—H30 | 125.0 |
C2—C3—C4 | 121.5 (3) | C30—C31—N1 | 105.9 (4) |
C2—C3—Cl2 | 119.2 (3) | C30—C31—H31 | 127.1 |
C4—C3—Cl2 | 119.3 (3) | N1—C31—H31 | 127.1 |
N6—C4—C5 | 121.0 (3) | N2—C32—N1 | 110.6 (4) |
N6—C4—C3 | 122.0 (3) | N2—C32—H32 | 124.7 |
C5—C4—C3 | 117.1 (3) | N1—C32—H32 | 124.7 |
C6—C5—C4 | 121.2 (3) | N1—C33—C34ii | 112.0 (3) |
C6—C5—H5 | 119.4 | N1—C33—H33A | 109.2 |
C4—C5—H5 | 119.4 | C34ii—C33—H33A | 109.2 |
C5—C6—C1 | 121.6 (3) | N1—C33—H33B | 109.2 |
C5—C6—Cl1 | 117.6 (2) | C34ii—C33—H33B | 109.2 |
C1—C6—Cl1 | 120.8 (3) | H33A—C33—H33B | 107.9 |
C8—C7—C12 | 117.2 (3) | C39—C34—C35 | 118.6 (4) |
C8—C7—S1 | 125.6 (3) | C39—C34—C33ii | 122.9 (4) |
C12—C7—S1 | 117.1 (3) | C35—C34—C33ii | 118.5 (4) |
C7—C8—C9 | 122.4 (4) | C36—C35—C34 | 121.9 (4) |
C7—C8—Cl3 | 121.2 (3) | C36—C35—H35 | 119.1 |
C9—C8—Cl3 | 116.4 (3) | C34—C35—H35 | 119.1 |
C8—C9—C10 | 121.0 (4) | C35—C36—C37 | 119.5 (5) |
C8—C9—H9 | 119.5 | C35—C36—H36 | 120.2 |
C10—C9—H9 | 119.5 | C37—C36—H36 | 120.2 |
N5—C10—C11 | 122.6 (4) | C36—C37—C38 | 120.5 (5) |
N5—C10—C9 | 120.5 (4) | C36—C37—H37 | 119.7 |
C11—C10—C9 | 116.9 (3) | C38—C37—H37 | 119.7 |
C10—C11—C12 | 121.7 (4) | C37—C38—C39 | 120.3 (4) |
C10—C11—Cl4 | 119.6 (3) | C37—C38—H38 | 119.8 |
C12—C11—Cl4 | 118.6 (3) | C39—C38—H38 | 119.8 |
C11—C12—C7 | 120.8 (4) | C38—C39—C34 | 119.1 (4) |
C11—C12—H12 | 119.6 | C38—C39—C40 | 118.3 (4) |
C7—C12—H12 | 119.6 | C34—C39—C40 | 122.6 (4) |
N8—C13—N7 | 111.7 (3) | N4—C40—C39 | 112.6 (3) |
N8—C13—H13 | 124.2 | N4—C40—H40A | 109.1 |
N7—C13—H13 | 124.2 | C39—C40—H40A | 109.1 |
C15—C14—N8 | 110.5 (4) | N4—C40—H40B | 109.1 |
C15—C14—H14 | 124.8 | C39—C40—H40B | 109.1 |
N8—C14—H14 | 124.8 | H40A—C40—H40B | 107.8 |
C14—C15—N7 | 105.4 (4) | C32—N1—C31 | 107.6 (3) |
C14—C15—H15 | 127.3 | C32—N1—C33 | 125.1 (4) |
N7—C15—H15 | 127.3 | C31—N1—C33 | 127.3 (4) |
C17—C16—N9 | 110.0 (4) | C32—N2—C30 | 105.9 (3) |
C17—C16—H16 | 125.0 | C32—N2—Ag2 | 128.8 (3) |
N9—C16—H16 | 125.0 | C30—N2—Ag2 | 125.3 (3) |
C16—C17—N10 | 105.4 (4) | C29—N3—C27 | 104.9 (4) |
C16—C17—H17 | 127.3 | C29—N3—Ag2 | 124.5 (3) |
N10—C17—H17 | 127.3 | C27—N3—Ag2 | 130.6 (3) |
N9—C18—N10 | 111.9 (4) | C29—N4—C28 | 107.8 (3) |
N9—C18—H18 | 124.0 | C29—N4—C40 | 125.9 (4) |
N10—C18—H18 | 124.0 | C28—N4—C40 | 126.2 (4) |
N10—C19—C20i | 112.7 (3) | C10—N5—H5A | 112 (4) |
N10—C19—H19A | 109.1 | C10—N5—H5B | 113 (4) |
C20i—C19—H19A | 109.1 | H5A—N5—H5B | 126 (5) |
N10—C19—H19B | 109.1 | C4—N6—H6A | 124 (5) |
C20i—C19—H19B | 109.1 | C4—N6—H6B | 120 (5) |
H19A—C19—H19B | 107.8 | H6A—N6—H6B | 113 (6) |
C21—C20—C25 | 118.5 (4) | C13—N7—C15 | 107.5 (3) |
C21—C20—C19i | 118.8 (4) | C13—N7—C26 | 126.3 (3) |
C25—C20—C19i | 122.7 (4) | C15—N7—C26 | 126.1 (4) |
C22—C21—C20 | 121.5 (4) | C13—N8—C14 | 104.8 (3) |
C22—C21—H21 | 119.3 | C13—N8—Ag1 | 125.4 (3) |
C20—C21—H21 | 119.3 | C14—N8—Ag1 | 129.8 (3) |
C21—C22—C23 | 120.5 (5) | C18—N9—C16 | 105.3 (3) |
C21—C22—H22 | 119.7 | C18—N9—Ag1 | 128.8 (3) |
C23—C22—H22 | 119.7 | C16—N9—Ag1 | 125.8 (3) |
C22—C23—C24 | 119.5 (5) | C18—N10—C17 | 107.4 (3) |
C22—C23—H23 | 120.3 | C18—N10—C19 | 125.5 (4) |
C24—C23—H23 | 120.3 | C17—N10—C19 | 127.1 (4) |
C25—C24—C23 | 120.2 (4) | H1A—O1W—H1B | 104 (5) |
C25—C24—H24 | 119.9 | H2A—O2W—H2B | 104 (6) |
C23—C24—H24 | 119.9 | H3A—O3W—H3B | 105 (4) |
C24—C25—C20 | 119.9 (4) | H4A—O4W—H4B | 101 (4) |
C24—C25—C26 | 118.0 (3) | O1—S1—O2 | 113.8 (2) |
C20—C25—C26 | 122.1 (4) | O1—S1—O3 | 112.0 (2) |
N7—C26—C25 | 112.3 (3) | O2—S1—O3 | 111.8 (2) |
N7—C26—H26A | 109.1 | O1—S1—C7 | 108.49 (17) |
C25—C26—H26A | 109.1 | O2—S1—C7 | 104.3 (2) |
N7—C26—H26B | 109.1 | O3—S1—C7 | 105.73 (18) |
C25—C26—H26B | 109.1 | O4—S2—O6 | 112.7 (2) |
H26A—C26—H26B | 107.9 | O4—S2—O5 | 113.29 (19) |
C28—C27—N3 | 110.4 (4) | O6—S2—O5 | 111.49 (18) |
C28—C27—H27 | 124.8 | O4—S2—C1 | 105.88 (18) |
N3—C27—H27 | 124.8 | O6—S2—C1 | 107.38 (17) |
C27—C28—N4 | 105.2 (4) | O5—S2—C1 | 105.46 (16) |
C27—C28—H28 | 127.4 | N9—Ag1—N8 | 175.91 (13) |
N4—C28—H28 | 127.4 | N3—Ag2—N2 | 178.95 (15) |
C6—C1—C2—C3 | 1.0 (5) | C33ii—C34—C39—C38 | −179.2 (3) |
S2—C1—C2—C3 | −179.5 (3) | C35—C34—C39—C40 | 179.1 (4) |
C1—C2—C3—C4 | −1.5 (5) | C33ii—C34—C39—C40 | 0.5 (5) |
C1—C2—C3—Cl2 | 179.6 (3) | C38—C39—C40—N4 | −95.9 (4) |
C2—C3—C4—N6 | −179.4 (4) | C34—C39—C40—N4 | 84.4 (5) |
Cl2—C3—C4—N6 | −0.5 (6) | N2—C32—N1—C31 | −0.5 (5) |
C2—C3—C4—C5 | 0.9 (5) | N2—C32—N1—C33 | −178.8 (3) |
Cl2—C3—C4—C5 | 179.8 (3) | C30—C31—N1—C32 | 0.6 (5) |
N6—C4—C5—C6 | −179.6 (4) | C30—C31—N1—C33 | 178.9 (4) |
C3—C4—C5—C6 | 0.1 (5) | C34ii—C33—N1—C32 | −145.3 (4) |
C4—C5—C6—C1 | −0.6 (5) | C34ii—C33—N1—C31 | 36.7 (6) |
C4—C5—C6—Cl1 | 178.6 (3) | N1—C32—N2—C30 | 0.2 (5) |
C2—C1—C6—C5 | 0.0 (5) | N1—C32—N2—Ag2 | −177.8 (2) |
S2—C1—C6—C5 | −179.4 (3) | C31—C30—N2—C32 | 0.2 (5) |
C2—C1—C6—Cl1 | −179.1 (2) | C31—C30—N2—Ag2 | 178.3 (3) |
S2—C1—C6—Cl1 | 1.5 (4) | N4—C29—N3—C27 | 0.6 (5) |
C12—C7—C8—C9 | −1.1 (5) | N4—C29—N3—Ag2 | 178.8 (3) |
S1—C7—C8—C9 | −176.0 (3) | C28—C27—N3—C29 | −0.6 (5) |
C12—C7—C8—Cl3 | 179.4 (3) | C28—C27—N3—Ag2 | −178.6 (3) |
S1—C7—C8—Cl3 | 4.5 (5) | N3—C29—N4—C28 | −0.4 (5) |
C7—C8—C9—C10 | 1.6 (6) | N3—C29—N4—C40 | −176.5 (3) |
Cl3—C8—C9—C10 | −178.9 (3) | C27—C28—N4—C29 | 0.0 (5) |
C8—C9—C10—N5 | 176.3 (4) | C27—C28—N4—C40 | 176.1 (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—C28 | 49.0 (6) |
C9—C10—C11—C12 | 0.5 (5) | N8—C13—N7—C15 | 1.5 (4) |
N5—C10—C11—Cl4 | 2.0 (5) | N8—C13—N7—C26 | 178.6 (3) |
C9—C10—C11—Cl4 | 179.6 (3) | C14—C15—N7—C13 | −1.2 (4) |
C10—C11—C12—C7 | 0.0 (5) | C14—C15—N7—C26 | −178.3 (4) |
Cl4—C11—C12—C7 | −179.1 (3) | C25—C26—N7—C13 | 124.6 (4) |
C8—C7—C12—C11 | 0.3 (5) | C25—C26—N7—C15 | −58.8 (5) |
S1—C7—C12—C11 | 175.7 (3) | N7—C13—N8—C14 | −1.2 (5) |
N8—C14—C15—N7 | 0.5 (5) | N7—C13—N8—Ag1 | 179.5 (2) |
N9—C16—C17—N10 | 0.1 (5) | C15—C14—N8—C13 | 0.4 (5) |
C25—C20—C21—C22 | −0.2 (6) | C15—C14—N8—Ag1 | 179.7 (3) |
C19i—C20—C21—C22 | −178.3 (4) | N10—C18—N9—C16 | −0.5 (4) |
C20—C21—C22—C23 | 0.0 (7) | N10—C18—N9—Ag1 | 175.9 (2) |
C21—C22—C23—C24 | 0.6 (8) | C17—C16—N9—C18 | 0.2 (5) |
C22—C23—C24—C25 | −0.8 (7) | C17—C16—N9—Ag1 | −176.3 (3) |
C23—C24—C25—C20 | 0.6 (6) | N9—C18—N10—C17 | 0.6 (5) |
C23—C24—C25—C26 | 179.5 (4) | N9—C18—N10—C19 | 178.9 (3) |
C21—C20—C25—C24 | −0.1 (5) | C16—C17—N10—C18 | −0.4 (5) |
C19i—C20—C25—C24 | 177.9 (3) | C16—C17—N10—C19 | −178.7 (4) |
C21—C20—C25—C26 | −179.0 (3) | C20i—C19—N10—C18 | 157.7 (4) |
C19i—C20—C25—C26 | −1.0 (5) | C20i—C19—N10—C17 | −24.3 (6) |
C24—C25—C26—N7 | 104.5 (4) | C8—C7—S1—O1 | −49.1 (4) |
C20—C25—C26—N7 | −76.6 (4) | C12—C7—S1—O1 | 135.9 (3) |
N3—C27—C28—N4 | 0.4 (5) | C8—C7—S1—O2 | −170.8 (3) |
N2—C30—C31—N1 | −0.5 (5) | C12—C7—S1—O2 | 14.2 (3) |
C39—C34—C35—C36 | −0.1 (6) | C8—C7—S1—O3 | 71.2 (4) |
C33ii—C34—C35—C36 | 178.5 (4) | C12—C7—S1—O3 | −103.8 (3) |
C34—C35—C36—C37 | 1.0 (7) | C2—C1—S2—O4 | 115.0 (3) |
C35—C36—C37—C38 | −1.0 (8) | C6—C1—S2—O4 | −65.6 (3) |
C36—C37—C38—C39 | 0.3 (7) | C2—C1—S2—O6 | −124.4 (3) |
C37—C38—C39—C34 | 0.5 (6) | C6—C1—S2—O6 | 55.1 (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—O5 | 174.1 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2W—H2A···O6 | 0.81 (6) | 2.15 (7) | 2.868 (5) | 148 (7) |
O3W—H3A···O2 | 0.82 (7) | 2.00 (7) | 2.819 (6) | 172 (9) |
O1W—H1A···O4iii | 0.80 (6) | 1.99 (6) | 2.762 (5) | 165 (7) |
N6—H6B···O2iv | 0.80 (3) | 2.19 (4) | 2.928 (5) | 154 (6) |
N5—H5B···O5v | 0.81 (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. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C14H14N4)2](C6H4Cl2NO3S)2·4H2O |
Mr | 1246.51 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 11.732 (6), 14.598 (6), 15.718 (6) |
α, β, γ (°) | 79.068 (12), 72.843 (19), 70.991 (17) |
V (Å3) | 2418.8 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.18 |
Crystal size (mm) | 0.35 × 0.25 × 0.24 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.716, 0.753 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19762, 10576, 6897 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.152, 0.96 |
No. of reflections | 10576 |
No. of parameters | 649 |
No. of restraints | 13 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.92, −0.36 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).
N2—Ag2 | 2.092 (3) | N8—Ag1 | 2.103 (3) |
N3—Ag2 | 2.090 (4) | N9—Ag1 | 2.100 (3) |
N9—Ag1—N8 | 175.91 (13) | N3—Ag2—N2 | 178.95 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2W—H2A···O6 | 0.81 (6) | 2.15 (7) | 2.868 (5) | 148 (7) |
O3W—H3A···O2 | 0.82 (7) | 2.00 (7) | 2.819 (6) | 172 (9) |
O1W—H1A···O4i | 0.80 (6) | 1.99 (6) | 2.762 (5) | 165 (7) |
N6—H6B···O2ii | 0.80 (3) | 2.19 (4) | 2.928 (5) | 154 (6) |
N5—H5B···O5iii | 0.81 (6) | 2.28 (6) | 2.913 (5) | 136 (5) |
Symmetry codes: (i) x−1, y, z+1; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
Acknowledgements
The authors thank the Science Foundation of Suihua University (grant No. K071001) for supporting this work.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).