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In the title compound, [Ag2(C9H12N4)2]Cl2·0.5H2O, each AgI atom is coordinated by two C atoms of two heterocyclic carbene ligands, displaying a nearly linear geometry. The Ag—Ag separation is quite long, indicating a very weak metal–metal inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022136/is2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022136/is2045Isup2.hkl
Contains datablock I

CCDC reference: 613738

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in solvent or counterion
  • R factor = 0.044
  • wR factor = 0.122
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT415_ALERT_2_B Short Inter D-H..H-X H7A .. H20 .. 1.97 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.38 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C2 .. 3.00 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[3,3'-dimethyl-3,3'-methylenebis(2,3-dihydro-1H- imidazole)]disilver(I)(Ag—Ag) dichloride hemihydrate top
Crystal data top
[Ag2(C9H12N4)2]Cl2·0.5H2OF(000) = 1284
Mr = 648.10Dx = 1.834 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4595 reflections
a = 7.436 (3) Åθ = 2.3–28.0°
b = 12.498 (4) ŵ = 1.92 mm1
c = 25.382 (8) ÅT = 298 K
β = 95.702 (6)°Plate, colourless
V = 2347.3 (14) Å30.36 × 0.14 × 0.07 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4076 independent reflections
Radiation source: fine-focus sealed tube2895 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 58
Tmin = 0.545, Tmax = 0.877k = 1414
11631 measured reflectionsl = 3029
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.2797P]
where P = (Fo2 + 2Fc2)/3
4076 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 1.59 e Å3
0 restraintsΔρmin = 0.67 e Å3
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*/UeqOcc. (<1)
Ag10.00855 (7)0.57564 (3)0.589794 (16)0.04468 (17)
Ag20.22652 (6)0.57933 (3)0.707936 (15)0.04179 (16)
Cl10.5165 (2)0.58662 (12)0.90127 (6)0.0619 (4)
Cl20.3973 (2)1.07330 (10)0.86482 (5)0.0479 (4)
N10.1372 (6)0.8003 (4)0.55445 (15)0.0415 (11)
N20.1315 (6)0.8151 (3)0.59151 (15)0.0325 (10)
N30.2937 (6)0.8172 (3)0.67768 (16)0.0344 (10)
N40.2444 (6)0.8053 (4)0.75884 (15)0.0403 (11)
N50.1402 (6)0.3505 (3)0.55391 (16)0.0415 (11)
N60.1203 (6)0.3343 (3)0.59455 (15)0.0358 (10)
N70.2801 (6)0.3374 (3)0.68209 (15)0.0350 (10)
N80.2303 (6)0.3570 (3)0.76234 (16)0.0395 (11)
O10.3895 (15)0.9249 (7)0.5077 (4)0.075 (3)0.50
H190.42510.98170.52400.090*0.50
H200.46280.92510.48380.090*0.50
C10.0002 (7)0.7418 (4)0.57952 (18)0.0338 (11)
C20.0787 (9)0.9179 (4)0.5743 (2)0.0487 (15)
H20.14640.98050.57820.058*
C30.0910 (10)0.9067 (5)0.5510 (2)0.0542 (16)
H30.16370.96090.53540.065*
C40.2450 (7)0.7464 (4)0.71461 (17)0.0341 (11)
C50.2895 (9)0.9108 (4)0.7511 (2)0.0483 (15)
H50.29680.96520.77610.058*
C60.3207 (9)0.9191 (4)0.6998 (2)0.0463 (15)
H60.35380.98060.68250.056*
C70.3073 (9)0.7541 (6)0.5318 (2)0.0664 (19)
H7A0.38400.80980.51620.100*
H7B0.36600.71920.55910.100*
H7C0.28410.70290.50510.100*
C80.3031 (7)0.7929 (4)0.62232 (18)0.0369 (12)
H8A0.33390.71810.61850.044*
H8B0.39750.83570.60890.044*
C90.2013 (9)0.7638 (5)0.8100 (2)0.0627 (18)
H9A0.20980.82060.83560.094*
H9B0.28520.70820.82150.094*
H9C0.08070.73550.80650.094*
C100.0040 (8)0.4081 (4)0.57886 (19)0.0361 (12)
C110.0581 (10)0.2360 (4)0.5803 (2)0.0548 (18)
H110.12010.17240.58820.066*
C120.0995 (9)0.2425 (5)0.5542 (2)0.0547 (16)
H120.16990.18700.53900.066*
C130.2357 (7)0.4118 (4)0.71632 (19)0.0359 (12)
C140.2740 (8)0.2499 (4)0.7555 (2)0.0493 (15)
H140.28610.19670.78120.059*
C150.2946 (9)0.2399 (4)0.7052 (2)0.0507 (15)
H150.31590.17600.68810.061*
C160.3083 (9)0.3977 (6)0.5273 (3)0.0667 (19)
H16A0.38580.34150.51260.100*
H16B0.27860.44460.49950.100*
H16C0.36920.43740.55260.100*
C170.2921 (7)0.3587 (4)0.62593 (19)0.0370 (12)
H17A0.38760.31550.61350.044*
H17B0.32230.43340.62120.044*
C180.1868 (10)0.4029 (5)0.8124 (2)0.0612 (18)
H18A0.19280.34800.83900.092*
H18B0.06710.43240.80800.092*
H18C0.27200.45830.82310.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0530 (3)0.0323 (2)0.0462 (3)0.0049 (2)0.0076 (2)0.00006 (16)
Ag20.0491 (3)0.0336 (2)0.0415 (3)0.00069 (19)0.00142 (19)0.00022 (16)
Cl10.0558 (11)0.0642 (10)0.0649 (9)0.0042 (8)0.0014 (8)0.0068 (7)
Cl20.0587 (10)0.0398 (7)0.0452 (7)0.0005 (7)0.0049 (7)0.0023 (5)
N10.039 (3)0.052 (3)0.033 (2)0.003 (2)0.001 (2)0.0112 (19)
N20.033 (3)0.030 (2)0.033 (2)0.0020 (19)0.0005 (19)0.0010 (16)
N30.027 (3)0.034 (2)0.041 (2)0.0017 (19)0.0019 (19)0.0044 (18)
N40.032 (3)0.052 (3)0.036 (2)0.009 (2)0.0024 (19)0.0099 (19)
N50.031 (3)0.049 (3)0.044 (2)0.008 (2)0.000 (2)0.0135 (19)
N60.041 (3)0.031 (2)0.035 (2)0.001 (2)0.001 (2)0.0018 (17)
N70.031 (3)0.034 (2)0.039 (2)0.0031 (19)0.0051 (19)0.0000 (18)
N80.032 (3)0.046 (3)0.040 (2)0.008 (2)0.0001 (19)0.0068 (19)
O10.079 (8)0.079 (7)0.068 (6)0.005 (5)0.013 (5)0.012 (5)
C10.033 (3)0.038 (3)0.031 (2)0.002 (2)0.006 (2)0.003 (2)
C20.059 (4)0.035 (3)0.050 (3)0.003 (3)0.000 (3)0.007 (2)
C30.055 (4)0.057 (4)0.049 (3)0.014 (3)0.001 (3)0.018 (3)
C40.028 (3)0.041 (3)0.032 (3)0.006 (2)0.003 (2)0.003 (2)
C50.046 (4)0.049 (3)0.048 (3)0.007 (3)0.010 (3)0.021 (3)
C60.050 (4)0.030 (3)0.057 (4)0.001 (3)0.008 (3)0.011 (2)
C70.040 (4)0.098 (5)0.057 (4)0.017 (4)0.016 (3)0.026 (3)
C80.031 (3)0.036 (3)0.043 (3)0.001 (2)0.004 (2)0.004 (2)
C90.067 (5)0.086 (5)0.035 (3)0.021 (4)0.004 (3)0.000 (3)
C100.034 (3)0.040 (3)0.034 (3)0.002 (2)0.005 (2)0.006 (2)
C110.078 (5)0.039 (3)0.042 (3)0.028 (3)0.014 (3)0.003 (2)
C120.055 (4)0.048 (3)0.061 (4)0.019 (3)0.009 (3)0.023 (3)
C130.032 (3)0.041 (3)0.034 (3)0.007 (2)0.003 (2)0.003 (2)
C140.051 (4)0.044 (3)0.051 (3)0.003 (3)0.005 (3)0.018 (2)
C150.062 (4)0.035 (3)0.052 (3)0.012 (3)0.011 (3)0.009 (2)
C160.045 (4)0.092 (5)0.060 (4)0.000 (4)0.010 (3)0.029 (4)
C170.030 (3)0.042 (3)0.040 (3)0.003 (2)0.007 (2)0.001 (2)
C180.063 (5)0.087 (5)0.033 (3)0.020 (4)0.003 (3)0.000 (3)
Geometric parameters (Å, º) top
Ag1—C12.095 (5)O1—H200.8557
Ag1—C102.113 (5)C2—C31.347 (9)
Ag1—Ag23.3179 (11)C2—H20.9300
Ag2—C42.098 (5)C3—H30.9300
Ag2—C132.105 (5)C5—C61.348 (8)
N1—C11.361 (6)C5—H50.9300
N1—C31.379 (7)C6—H60.9300
N1—C71.456 (7)C7—H7A0.9600
N2—C11.351 (6)C7—H7B0.9600
N2—C21.401 (6)C7—H7C0.9600
N2—C81.455 (6)C8—H8A0.9700
N3—C41.364 (6)C8—H8B0.9700
N3—C61.399 (6)C9—H9A0.9600
N3—C81.446 (6)C9—H9B0.9600
N4—C41.343 (6)C9—H9C0.9600
N4—C51.379 (7)C11—C121.290 (9)
N4—C91.463 (7)C11—H110.9300
N5—C101.348 (6)C12—H120.9300
N5—C121.384 (7)C14—C151.306 (8)
N5—C161.483 (7)C14—H140.9300
N6—C101.339 (6)C15—H150.9300
N6—C111.349 (6)C16—H16A0.9600
N6—C171.469 (6)C16—H16B0.9600
N7—C131.336 (6)C16—H16C0.9600
N7—C151.352 (6)C17—H17A0.9700
N7—C171.462 (6)C17—H17B0.9700
N8—C131.358 (6)C18—H18A0.9600
N8—C141.393 (7)C18—H18B0.9600
N8—C181.458 (7)C18—H18C0.9600
O1—H190.8510
C1—Ag1—C10164.79 (19)N1—C7—H7C109.5
C1—Ag1—Ag294.51 (13)H7A—C7—H7C109.5
C10—Ag1—Ag296.81 (14)H7B—C7—H7C109.5
C4—Ag2—C13168.65 (18)N3—C8—N2111.0 (4)
C4—Ag2—Ag196.39 (12)N3—C8—H8A109.4
C13—Ag2—Ag194.95 (13)N2—C8—H8A109.4
C1—N1—C3111.5 (5)N3—C8—H8B109.4
C1—N1—C7123.7 (5)N2—C8—H8B109.4
C3—N1—C7124.7 (5)H8A—C8—H8B108.0
C1—N2—C2112.2 (4)N4—C9—H9A109.5
C1—N2—C8124.6 (4)N4—C9—H9B109.5
C2—N2—C8123.0 (4)H9A—C9—H9B109.5
C4—N3—C6110.7 (4)N4—C9—H9C109.5
C4—N3—C8125.0 (4)H9A—C9—H9C109.5
C6—N3—C8124.2 (4)H9B—C9—H9C109.5
C4—N4—C5112.5 (4)N6—C10—N5103.6 (4)
C4—N4—C9124.5 (5)N6—C10—Ag1131.6 (4)
C5—N4—C9122.9 (5)N5—C10—Ag1124.7 (4)
C10—N5—C12111.4 (5)C12—C11—N6110.5 (6)
C10—N5—C16124.2 (5)C12—C11—H11124.8
C12—N5—C16124.4 (5)N6—C11—H11124.8
C10—N6—C11109.9 (5)C11—C12—N5104.6 (5)
C10—N6—C17123.7 (4)C11—C12—H12127.7
C11—N6—C17126.2 (5)N5—C12—H12127.7
C13—N7—C15111.1 (4)N7—C13—N8103.8 (4)
C13—N7—C17123.4 (4)N7—C13—Ag2129.4 (4)
C15—N7—C17125.3 (4)N8—C13—Ag2125.8 (4)
C13—N8—C14110.5 (4)C15—C14—N8105.4 (5)
C13—N8—C18125.4 (5)C15—C14—H14127.3
C14—N8—C18124.2 (4)N8—C14—H14127.3
H19—O1—H2098.8C14—C15—N7109.0 (5)
N2—C1—N1103.5 (4)C14—C15—H15125.5
N2—C1—Ag1132.4 (4)N7—C15—H15125.5
N1—C1—Ag1124.0 (4)N5—C16—H16A109.5
C3—C2—N2105.3 (5)N5—C16—H16B109.5
C3—C2—H2127.4H16A—C16—H16B109.5
N2—C2—H2127.4N5—C16—H16C109.5
C2—C3—N1107.5 (5)H16A—C16—H16C109.5
C2—C3—H3126.2H16B—C16—H16C109.5
N1—C3—H3126.2N7—C17—N6110.9 (4)
N4—C4—N3104.0 (4)N7—C17—H17A109.5
N4—C4—Ag2127.4 (4)N6—C17—H17A109.5
N3—C4—Ag2127.6 (3)N7—C17—H17B109.5
C6—C5—N4106.2 (4)N6—C17—H17B109.5
C6—C5—H5126.9H17A—C17—H17B108.0
N4—C5—H5126.9N8—C18—H18A109.5
C5—C6—N3106.6 (5)N8—C18—H18B109.5
C5—C6—H6126.7H18A—C18—H18B109.5
N3—C6—H6126.7N8—C18—H18C109.5
N1—C7—H7A109.5H18A—C18—H18C109.5
N1—C7—H7B109.5H18B—C18—H18C109.5
H7A—C7—H7B109.5
 

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