Literature DB >> 21522610

Potassium bis-[bis-(1-benzyl-3-methyl-imidazolium)silver(I)] tris-(hexa-fluoridophosphate).

Rosenani A Haque, Abbas Washeel Salman, Choong Kah Whai, Ching Kheng Quah, Hoong-Kun Fun.   

Abstract

In the title compound, K[Ag(C(11)H(12)N(2))(2)](2)(PF(6))(3), the 12-coordinate potassium cation lies on a crystallographic twofold axis and one of the hexa-fluoro-phosphate anions is generated by symmetry. In the complex cation, the Ag(I) ion is coordinated by two C atoms; the two imidazolium rings are orientated at a dihedral angle of 8.14 (14)°. In the 1-benzyl-3-methyl-imidazolium units, the dihedral angles between imidazolium and phenyl rings are 80.47 (15) and 76.53 (14)°. The F atoms of the general-position hexa-fluoro-phosphate anion are disordered over two sets of sites in a 0.767 (17):0.233 (17) ratio. In the crystal, the hexa-fluoro-phosphate anions link the cations into three-dimensional networks via inter-molecular C-H⋯F hydrogen bonds and are further consolidated by π-π stacking [centroid-centroid distances = 3.5518 (15) Å] inter-actions.

Entities:  

Year:  2010        PMID： 21522610      PMCID： PMC3050194          DOI： 10.1107/S1600536810051925

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to and the biological activity of carbene derivatives, see: Lee et al. (2001 ▶); Bourissou et al. (2000 ▶); Herrmann & Köcher (1997 ▶); Hermann et al. (1996 ▶); Zhou et al. (2008 ▶); Wang & Lin (1998 ▶); Lin & Vasam (2007 ▶); Ray et al. (2007 ▶); Özdemir et al. (2010 ▶); Medvetz et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Haque et al. (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

K[Ag(C11H12N2)2]2(PF6)3 M = 1378.65 Monoclinic, a = 19.917 (2) Å b = 23.047 (2) Å c = 11.5787 (12) Å β = 103.108 (3)° V = 5176.4 (9) Å3 Z = 4 Mo Kα radiation μ = 1.04 mm−1 T = 100 K 0.49 × 0.42 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.632, T max = 0.847 66454 measured reflections 7528 independent reflections 7058 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.124 S = 1.11 7528 reflections 372 parameters 51 restraints H-atom parameters constrained Δρmax = 1.68 e Å−3 Δρmin = −0.91 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051925/hb5767sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051925/hb5767Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
K[Ag(C11H12N2)2]2(PF6)3F(000) = 2752
Mr = 1378.65Dx = 1.769 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9934 reflections
a = 19.917 (2) Åθ = 2.5–37.7°
b = 23.047 (2) ŵ = 1.04 mm−1
c = 11.5787 (12) ÅT = 100 K
β = 103.108 (3)°Block, colourless
V = 5176.4 (9) Å30.49 × 0.42 × 0.17 mm
Z = 4
Bruker SMART APEXII DUO CCD diffractometer7528 independent reflections
Radiation source: fine-focus sealed tube7058 reflections with I > 2σ(I)
graphiteRint = 0.050
φ and ω scansθmax = 30.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −28→27
Tmin = 0.632, Tmax = 0.847k = −32→32
66454 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.072P)2 + 12.8353P] where P = (Fo2 + 2Fc2)/3
7528 reflections(Δ/σ)max = 0.001
372 parametersΔρmax = 1.68 e Å−3
51 restraintsΔρmin = −0.91 e Å−3
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/UeqOcc. (<1)
Ag10.313945 (8)0.186742 (7)0.040241 (15)0.02197 (7)
N10.25175 (10)0.13210 (9)−0.20778 (18)0.0220 (4)
N20.22372 (10)0.08198 (8)−0.07022 (18)0.0219 (4)
N30.39227 (10)0.29823 (9)0.12655 (19)0.0236 (4)
N40.37731 (10)0.25291 (9)0.27988 (18)0.0227 (4)
C10.25902 (11)0.13002 (10)−0.0883 (2)0.0205 (4)
C20.21334 (13)0.08620 (10)−0.2628 (2)0.0250 (4)
H2A0.20200.0785−0.34370.030*
C30.19529 (12)0.05430 (10)−0.1766 (2)0.0250 (4)
H3A0.16900.0205−0.18660.030*
C40.22223 (13)0.05954 (11)0.0474 (2)0.0257 (4)
H4A0.18220.03480.04140.031*
H4B0.21800.09170.09940.031*
C50.28652 (13)0.02546 (10)0.1002 (2)0.0240 (4)
C60.3103 (2)−0.01707 (15)0.0352 (3)0.0424 (8)
H6A0.2872−0.0240−0.04290.051*
C70.3684 (2)−0.04945 (18)0.0855 (3)0.0580 (11)
H7A0.3843−0.07770.04090.070*
C80.40217 (19)−0.04004 (17)0.1999 (3)0.0491 (9)
H8A0.4405−0.06240.23370.059*
C90.37995 (17)0.00225 (15)0.2653 (3)0.0430 (7)
H9A0.40350.00880.34320.052*
C100.32197 (15)0.03570 (12)0.2157 (2)0.0310 (5)
H10A0.30730.06470.26020.037*
C110.28146 (14)0.17678 (12)−0.2715 (2)0.0288 (5)
H11A0.29540.2095−0.22030.043*
H11B0.24760.1889−0.34010.043*
H11C0.32080.1612−0.29570.043*
C120.36699 (11)0.24814 (10)0.1601 (2)0.0210 (4)
C130.41715 (12)0.33379 (11)0.2217 (2)0.0272 (5)
H13A0.43630.37050.21960.033*
C140.40833 (14)0.30508 (12)0.3196 (2)0.0281 (5)
H14A0.42070.31790.39770.034*
C150.36321 (12)0.20739 (12)0.3596 (2)0.0267 (5)
H15A0.33390.17800.31380.032*
H15B0.33890.22400.41540.032*
C160.42893 (13)0.17983 (11)0.4265 (2)0.0242 (4)
C170.45994 (14)0.19764 (13)0.5417 (2)0.0303 (5)
H17A0.43960.22640.57860.036*
C180.52170 (15)0.17182 (16)0.6012 (3)0.0367 (6)
H18A0.54290.18430.67710.044*
C190.55127 (14)0.12872 (14)0.5493 (3)0.0362 (6)
H19A0.59180.11140.59060.043*
C200.52082 (16)0.11032 (13)0.4341 (3)0.0364 (6)
H20A0.54130.08120.39820.044*
C210.45960 (14)0.13608 (12)0.3739 (2)0.0304 (5)
H21A0.43900.12380.29760.036*
C220.39464 (16)0.31203 (12)0.0039 (3)0.0310 (5)
H22A0.35190.3009−0.04830.046*
H22B0.43190.2912−0.01710.046*
H22C0.40170.3530−0.00320.046*
K10.00000.08540 (3)0.25000.02658 (15)
P10.16091 (3)0.15499 (3)0.34572 (6)0.02586 (13)
F10.1121 (3)0.1369 (2)0.4315 (4)0.0663 (14)0.767 (17)
F20.2272 (4)0.1299 (3)0.4279 (6)0.079 (2)0.767 (17)
F30.1443 (3)0.0957 (2)0.2724 (5)0.0475 (11)0.767 (17)
F40.1743 (3)0.2155 (3)0.4111 (6)0.074 (2)0.767 (17)
F50.09354 (17)0.18170 (17)0.2567 (5)0.0448 (9)0.767 (17)
F60.20487 (19)0.1757 (3)0.2508 (3)0.0307 (8)0.767 (17)
F1A0.1259 (10)0.1383 (9)0.4538 (18)0.065 (4)*0.233 (17)
F2A0.2363 (8)0.1276 (6)0.4325 (14)0.035 (3)*0.233 (17)
F3A0.1448 (7)0.0905 (6)0.2965 (13)0.027 (2)*0.233 (17)
F4A0.1841 (8)0.2166 (5)0.4153 (12)0.029 (3)*0.233 (17)
F5A0.0936 (7)0.1771 (6)0.2895 (16)0.043 (3)*0.233 (17)
F6A0.2099 (8)0.1626 (7)0.2645 (16)0.045 (4)*0.233 (17)
P20.00000.00000.00000.02900 (19)
F70.00552 (14)0.06866 (9)0.0087 (2)0.0535 (5)
F8−0.05948 (12)0.00366 (12)−0.1174 (2)0.0589 (6)
F9−0.05557 (11)0.00116 (10)0.0805 (2)0.0524 (6)
U11U22U33U12U13U23
Ag10.02133 (11)0.02546 (11)0.01764 (11)−0.00150 (5)0.00131 (7)−0.00177 (5)
N10.0217 (8)0.0241 (9)0.0194 (8)0.0014 (7)0.0034 (7)0.0010 (7)
N20.0204 (8)0.0223 (8)0.0225 (9)−0.0001 (7)0.0039 (7)−0.0005 (7)
N30.0211 (8)0.0259 (9)0.0222 (9)0.0023 (7)0.0014 (7)0.0023 (7)
N40.0189 (8)0.0283 (9)0.0195 (9)0.0010 (7)0.0013 (7)−0.0030 (7)
C10.0188 (9)0.0221 (9)0.0192 (9)0.0011 (7)0.0017 (7)−0.0002 (7)
C20.0263 (10)0.0251 (10)0.0211 (10)0.0029 (8)0.0005 (8)−0.0038 (8)
C30.0242 (10)0.0233 (10)0.0252 (11)−0.0003 (8)0.0009 (8)−0.0034 (8)
C40.0250 (10)0.0291 (11)0.0250 (11)0.0018 (8)0.0100 (9)0.0034 (9)
C50.0291 (11)0.0210 (9)0.0238 (10)−0.0004 (8)0.0100 (9)0.0043 (8)
C60.067 (2)0.0360 (15)0.0256 (13)0.0220 (14)0.0136 (14)0.0044 (10)
C70.086 (3)0.053 (2)0.0436 (18)0.044 (2)0.0335 (19)0.0202 (16)
C80.0438 (16)0.0560 (19)0.0522 (19)0.0212 (15)0.0211 (15)0.0304 (16)
C90.0385 (15)0.0455 (16)0.0392 (16)−0.0030 (12)−0.0034 (12)0.0127 (13)
C100.0387 (13)0.0263 (11)0.0262 (12)−0.0012 (10)0.0034 (10)0.0015 (9)
C110.0297 (12)0.0323 (11)0.0246 (11)−0.0016 (9)0.0066 (9)0.0052 (9)
C120.0179 (9)0.0263 (10)0.0172 (9)0.0019 (7)0.0006 (7)−0.0015 (7)
C130.0213 (10)0.0249 (10)0.0334 (12)0.0011 (8)0.0021 (9)−0.0057 (9)
C140.0254 (11)0.0308 (11)0.0249 (11)0.0011 (9)−0.0009 (9)−0.0081 (9)
C150.0203 (10)0.0397 (13)0.0199 (10)−0.0002 (9)0.0041 (8)0.0011 (9)
C160.0216 (10)0.0307 (11)0.0197 (10)−0.0015 (8)0.0032 (8)0.0039 (8)
C170.0277 (12)0.0409 (13)0.0209 (11)0.0024 (10)0.0029 (9)0.0006 (10)
C180.0289 (12)0.0556 (17)0.0216 (12)−0.0011 (12)−0.0028 (10)0.0072 (11)
C190.0235 (11)0.0468 (15)0.0384 (14)0.0035 (10)0.0071 (10)0.0213 (12)
C200.0362 (14)0.0366 (13)0.0395 (15)0.0091 (11)0.0150 (12)0.0105 (11)
C210.0306 (12)0.0355 (13)0.0256 (11)−0.0010 (10)0.0079 (9)0.0004 (9)
C220.0321 (13)0.0351 (13)0.0261 (12)0.0015 (9)0.0073 (10)0.0070 (9)
K10.0297 (3)0.0282 (3)0.0220 (3)0.0000.0061 (3)0.000
P10.0312 (3)0.0280 (3)0.0191 (3)−0.0048 (2)0.0072 (2)−0.0045 (2)
F10.100 (3)0.076 (2)0.0405 (19)−0.052 (2)0.053 (2)−0.0271 (16)
F20.069 (3)0.101 (4)0.049 (2)0.005 (2)−0.023 (2)0.026 (2)
F30.066 (2)0.0377 (17)0.047 (2)−0.0194 (14)0.0316 (19)−0.0191 (17)
F40.079 (4)0.066 (2)0.092 (3)−0.042 (2)0.050 (3)−0.057 (3)
F50.0300 (13)0.065 (2)0.0393 (19)0.0101 (10)0.0067 (13)0.0182 (15)
F60.0294 (13)0.0433 (19)0.0212 (12)−0.0078 (12)0.0091 (9)0.0043 (12)
P20.0251 (4)0.0345 (5)0.0291 (4)−0.0088 (3)0.0096 (3)−0.0127 (3)
F70.0752 (15)0.0358 (9)0.0569 (13)−0.0114 (9)0.0306 (11)−0.0140 (9)
F80.0468 (12)0.0796 (16)0.0428 (11)0.0010 (11)−0.0054 (9)−0.0118 (11)
F90.0472 (11)0.0645 (13)0.0559 (12)−0.0226 (10)0.0333 (10)−0.0300 (10)
Ag1—C122.092 (2)C17—H17A0.9300
Ag1—C12.093 (2)C18—C191.361 (5)
N1—C11.359 (3)C18—H18A0.9300
N1—C21.374 (3)C19—C201.400 (5)
N1—C111.467 (3)C19—H19A0.9300
N2—C11.353 (3)C20—C211.393 (4)
N2—C31.389 (3)C20—H20A0.9300
N2—C41.463 (3)C21—H21A0.9300
N3—C121.351 (3)C22—H22A0.9600
N3—C131.372 (3)C22—H22B0.9600
N3—C221.467 (3)C22—H22C0.9600
N4—C121.360 (3)K1—F5Ai2.786 (14)
N4—C141.382 (3)K1—F5A2.786 (14)
N4—C151.466 (3)K1—F92.803 (2)
C2—C31.352 (4)K1—F9i2.803 (2)
C2—H2A0.9300K1—F3Ai2.813 (13)
C3—H3A0.9300K1—F3A2.813 (13)
C4—C51.509 (3)K1—F32.836 (5)
C4—H4A0.9700K1—F3i2.836 (5)
C4—H4B0.9700K1—F7i2.848 (2)
C5—C61.383 (4)K1—F72.848 (2)
C5—C101.384 (4)K1—F52.887 (4)
C6—C71.390 (5)K1—F5i2.887 (4)
C6—H6A0.9300P1—F5A1.444 (14)
C7—C81.359 (6)P1—F6A1.512 (16)
C7—H7A0.9300P1—F21.554 (5)
C8—C91.368 (6)P1—F41.580 (5)
C8—H8A0.9300P1—F11.596 (3)
C9—C101.399 (4)P1—F3A1.597 (14)
C9—H9A0.9300P1—F31.604 (4)
C10—H10A0.9300P1—F1A1.612 (17)
C11—H11A0.9600P1—F51.617 (4)
C11—H11B0.9600P1—F61.625 (3)
C11—H11C0.9600P1—F4A1.646 (14)
C13—C141.358 (4)P1—F2A1.725 (16)
C13—H13A0.9300P2—F71.588 (2)
C14—H14A0.9300P2—F7ii1.588 (2)
C15—C161.502 (3)P2—F81.590 (2)
C15—H15A0.9700P2—F8ii1.590 (2)
C15—H15B0.9700P2—F91.6010 (18)
C16—C211.389 (4)P2—F9ii1.6010 (18)
C16—C171.399 (4)P2—K1ii3.5004 (5)
C17—C181.399 (4)F8—K1ii2.966 (3)
C12—Ag1—C1175.99 (9)F5Ai—K1—F796.6 (4)
C1—N1—C2111.4 (2)F5A—K1—F795.2 (4)
C1—N1—C11125.1 (2)F9—K1—F746.86 (6)
C2—N1—C11123.6 (2)F9i—K1—F7119.74 (7)
C1—N2—C3111.1 (2)F3Ai—K1—F794.8 (3)
C1—N2—C4123.6 (2)F3A—K1—F785.8 (3)
C3—N2—C4124.9 (2)F3—K1—F780.62 (12)
C12—N3—C13111.7 (2)F3i—K1—F7100.69 (13)
C12—N3—C22124.0 (2)F7i—K1—F7164.42 (9)
C13—N3—C22124.3 (2)F5Ai—K1—F579.9 (2)
C12—N4—C14111.2 (2)F5A—K1—F57.7 (3)
C12—N4—C15125.3 (2)F9—K1—F5134.50 (12)
C14—N4—C15123.2 (2)F9i—K1—F5111.32 (10)
N2—C1—N1104.30 (19)F3Ai—K1—F5126.9 (3)
N2—C1—Ag1127.39 (17)F3A—K1—F548.3 (3)
N1—C1—Ag1128.29 (17)F3—K1—F545.51 (12)
C3—C2—N1106.8 (2)F3i—K1—F5124.94 (13)
C3—C2—H2A126.6F7i—K1—F5104.25 (12)
N1—C2—H2A126.6F7—K1—F587.83 (12)
C2—C3—N2106.4 (2)F5Ai—K1—F5i7.7 (3)
C2—C3—H3A126.8F5A—K1—F5i79.9 (2)
N2—C3—H3A126.8F9—K1—F5i111.32 (10)
N2—C4—C5111.51 (19)F9i—K1—F5i134.51 (12)
N2—C4—H4A109.3F3Ai—K1—F5i48.3 (3)
C5—C4—H4A109.3F3A—K1—F5i126.9 (3)
N2—C4—H4B109.3F3—K1—F5i124.94 (13)
C5—C4—H4B109.3F3i—K1—F5i45.51 (12)
H4A—C4—H4B108.0F7i—K1—F5i87.83 (12)
C6—C5—C10119.0 (3)F7—K1—F5i104.25 (12)
C6—C5—C4120.8 (2)F5—K1—F5i79.54 (13)
C10—C5—C4120.2 (2)F5A—P1—F6A110.1 (11)
C5—C6—C7120.5 (3)F5A—P1—F2168.8 (7)
C5—C6—H6A119.8F6A—P1—F281.1 (8)
C7—C6—H6A119.8F5A—P1—F486.8 (6)
C8—C7—C6120.3 (3)F6A—P1—F497.7 (7)
C8—C7—H7A119.9F2—P1—F490.4 (4)
C6—C7—H7A119.9F5A—P1—F174.8 (7)
C7—C8—C9120.2 (3)F6A—P1—F1171.4 (7)
C7—C8—H8A119.9F2—P1—F194.3 (4)
C9—C8—H8A119.9F4—P1—F189.6 (3)
C8—C9—C10120.4 (3)F5A—P1—F3A94.3 (7)
C8—C9—H9A119.8F6A—P1—F3A89.5 (8)
C10—C9—H9A119.8F2—P1—F3A87.0 (6)
C5—C10—C9119.7 (3)F4—P1—F3A171.9 (6)
C5—C10—H10A120.1F1—P1—F3A83.0 (6)
C9—C10—H10A120.1F5A—P1—F390.2 (6)
N1—C11—H11A109.5F6A—P1—F381.6 (7)
N1—C11—H11B109.5F2—P1—F393.0 (4)
H11A—C11—H11B109.5F4—P1—F3176.4 (4)
N1—C11—H11C109.5F1—P1—F391.4 (2)
H11A—C11—H11C109.5F5A—P1—F1A85.1 (8)
H11B—C11—H11C109.5F6A—P1—F1A164.8 (11)
N3—C12—N4104.1 (2)F2—P1—F1A83.9 (8)
N3—C12—Ag1123.54 (16)F4—P1—F1A83.9 (8)
N4—C12—Ag1131.89 (17)F3A—P1—F1A88.1 (8)
C14—C13—N3106.7 (2)F3—P1—F1A97.7 (8)
C14—C13—H13A126.6F6A—P1—F596.8 (8)
N3—C13—H13A126.6F2—P1—F5177.9 (3)
C13—C14—N4106.2 (2)F4—P1—F589.7 (3)
C13—C14—H14A126.9F1—P1—F587.8 (3)
N4—C14—H14A126.9F3A—P1—F593.2 (5)
N4—C15—C16110.98 (19)F3—P1—F586.9 (3)
N4—C15—H15A109.4F1A—P1—F598.3 (7)
C16—C15—H15A109.4F5A—P1—F6100.3 (8)
N4—C15—H15B109.4F2—P1—F690.6 (4)
C16—C15—H15B109.4F4—P1—F690.4 (3)
H15A—C15—H15B108.0F1—P1—F6175.1 (4)
C21—C16—C17119.2 (2)F3A—P1—F697.3 (5)
C21—C16—C15120.0 (2)F3—P1—F688.3 (2)
C17—C16—C15120.8 (2)F1A—P1—F6172.0 (8)
C18—C17—C16119.6 (3)F5—P1—F687.3 (3)
C18—C17—H17A120.2F5A—P1—F4A92.6 (7)
C16—C17—H17A120.2F6A—P1—F4A93.2 (8)
C19—C18—C17120.9 (3)F2—P1—F4A85.2 (5)
C19—C18—H18A119.6F1—P1—F4A93.6 (6)
C17—C18—H18A119.6F3A—P1—F4A171.2 (7)
C18—C19—C20120.3 (3)F3—P1—F4A174.7 (6)
C18—C19—H19A119.9F1A—P1—F4A87.1 (9)
C20—C19—H19A119.9F5—P1—F4A94.8 (4)
C21—C20—C19119.2 (3)F6—P1—F4A86.8 (6)
C21—C20—H20A120.4F5A—P1—F2A171.1 (9)
C19—C20—H20A120.4F6A—P1—F2A78.8 (8)
C16—C21—C20120.8 (3)F4—P1—F2A90.8 (5)
C16—C21—H21A119.6F1—P1—F2A96.6 (6)
C20—C21—H21A119.6F3A—P1—F2A86.9 (6)
N3—C22—H22A109.5F3—P1—F2A92.5 (5)
N3—C22—H22B109.5F1A—P1—F2A86.2 (8)
H22A—C22—H22B109.5F5—P1—F2A175.6 (5)
N3—C22—H22C109.5F6—P1—F2A88.3 (5)
H22A—C22—H22C109.5F4A—P1—F2A85.4 (6)
H22B—C22—H22C109.5P1—F1—K197.5 (2)
F5Ai—K1—F5A81.3 (6)P1—F3—K1101.7 (2)
F5Ai—K1—F9105.5 (3)P1—F5—K199.30 (19)
F5A—K1—F9141.6 (4)P1—F1A—K185.7 (9)
F5Ai—K1—F9i141.6 (4)P1—F3A—K1102.8 (6)
F5A—K1—F9i105.5 (3)P1—F5A—K1108.9 (7)
F9—K1—F9i92.34 (12)F7—P2—F7ii180.0
F5Ai—K1—F3Ai47.0 (4)F7—P2—F891.64 (14)
F5A—K1—F3Ai128.2 (4)F7ii—P2—F888.36 (14)
F9—K1—F3Ai70.8 (3)F7—P2—F8ii88.36 (14)
F9i—K1—F3Ai112.8 (3)F7ii—P2—F8ii91.64 (14)
F5Ai—K1—F3A128.2 (4)F8—P2—F8ii180.0
F5A—K1—F3A47.0 (4)F7—P2—F989.64 (12)
F9—K1—F3A112.8 (3)F7ii—P2—F990.36 (12)
F9i—K1—F3A70.8 (3)F8—P2—F991.02 (13)
F3Ai—K1—F3A175.2 (5)F8ii—P2—F988.99 (13)
F5Ai—K1—F3125.3 (3)F7—P2—F9ii90.36 (12)
F5A—K1—F345.2 (3)F7ii—P2—F9ii89.64 (12)
F9—K1—F3110.65 (9)F8—P2—F9ii88.98 (13)
F9i—K1—F376.28 (14)F8ii—P2—F9ii91.02 (13)
F3Ai—K1—F3170.9 (3)F9—P2—F9ii179.999 (1)
F3A—K1—F36.1 (3)F7—P2—K1ii126.84 (8)
F5Ai—K1—F3i45.2 (3)F7ii—P2—K1ii53.16 (8)
F5A—K1—F3i125.3 (3)F8—P2—K1ii57.49 (9)
F9—K1—F3i76.28 (14)F8ii—P2—K1ii122.51 (9)
F9i—K1—F3i110.65 (9)F9—P2—K1ii128.37 (7)
F3Ai—K1—F3i6.1 (3)F9ii—P2—K1ii51.63 (7)
F3A—K1—F3i170.9 (3)F7—P2—K153.16 (8)
F3—K1—F3i170.4 (2)F7ii—P2—K1126.84 (8)
F5Ai—K1—F7i95.2 (4)F8—P2—K1122.51 (9)
F5A—K1—F7i96.6 (4)F8ii—P2—K157.49 (9)
F9—K1—F7i119.74 (7)F9—P2—K151.63 (7)
F9i—K1—F7i46.87 (6)F9ii—P2—K1128.37 (7)
F3Ai—K1—F7i85.8 (3)K1ii—P2—K1180.0
F3A—K1—F7i94.8 (3)P2—F7—K1100.34 (11)
F3—K1—F7i100.69 (13)P2—F8—K1ii95.64 (11)
F3i—K1—F7i80.62 (12)P2—F9—K1101.77 (9)
C3—N2—C1—N10.4 (2)F5—P1—F3A—K1−36.3 (6)
C4—N2—C1—N1174.6 (2)F6—P1—F3A—K1−124.0 (4)
C3—N2—C1—Ag1−178.37 (16)F2A—P1—F3A—K1148.1 (7)
C4—N2—C1—Ag1−4.2 (3)F5Ai—K1—F3A—P122.0 (8)
C2—N1—C1—N2−0.5 (2)F5A—K1—F3A—P116.0 (7)
C11—N1—C1—N2−179.7 (2)F9—K1—F3A—P1156.4 (5)
C2—N1—C1—Ag1178.26 (16)F9i—K1—F3A—P1−119.4 (7)
C11—N1—C1—Ag1−1.0 (3)F3—K1—F3A—P186 (3)
C1—N1—C2—C30.4 (3)F7i—K1—F3A—P1−78.5 (6)
C11—N1—C2—C3179.6 (2)F7—K1—F3A—P1117.1 (6)
N1—C2—C3—N2−0.1 (3)F5—K1—F3A—P126.3 (5)
C1—N2—C3—C2−0.2 (3)F5i—K1—F3A—P112.4 (8)
C4—N2—C3—C2−174.3 (2)F6A—P1—F5A—K1115.1 (10)
C1—N2—C4—C5−79.8 (3)F2—P1—F5A—K1−72 (3)
C3—N2—C4—C593.6 (3)F4—P1—F5A—K1−147.9 (7)
N2—C4—C5—C6−48.9 (3)F1—P1—F5A—K1−57.5 (6)
N2—C4—C5—C10132.3 (2)F3A—P1—F5A—K124.0 (10)
C10—C5—C6—C70.8 (5)F3—P1—F5A—K134.0 (7)
C4—C5—C6—C7−178.1 (3)F1A—P1—F5A—K1−63.7 (11)
C5—C6—C7—C80.6 (6)F5—P1—F5A—K1109 (3)
C6—C7—C8—C9−1.4 (6)F6—P1—F5A—K1122.2 (7)
C7—C8—C9—C100.7 (6)F4A—P1—F5A—K1−150.6 (8)
C6—C5—C10—C9−1.4 (4)F5Ai—K1—F5A—P1166.3 (13)
C4—C5—C10—C9177.5 (3)F9—K1—F5A—P1−89.6 (10)
C8—C9—C10—C50.7 (5)F9i—K1—F5A—P125.1 (9)
C13—N3—C12—N4−0.6 (3)F3Ai—K1—F5A—P1162.0 (8)
C22—N3—C12—N4177.7 (2)F3—K1—F5A—P1−26.5 (6)
C13—N3—C12—Ag1172.52 (16)F3i—K1—F5A—P1155.2 (7)
C22—N3—C12—Ag1−9.2 (3)F7i—K1—F5A—P172.1 (9)
C14—N4—C12—N30.1 (3)F7—K1—F5A—P1−97.8 (9)
C15—N4—C12—N3−175.1 (2)F5—K1—F5A—P1−115 (3)
C14—N4—C12—Ag1−172.17 (18)F5i—K1—F5A—P1158.7 (10)
C15—N4—C12—Ag112.6 (3)F5Ai—K1—P2—F750.6 (3)
C12—N3—C13—C140.8 (3)F5A—K1—P2—F7−41.6 (4)
C22—N3—C13—C14−177.4 (2)F9—K1—P2—F7125.66 (18)
N3—C13—C14—N4−0.7 (3)F9i—K1—P2—F7−152.39 (13)
C12—N4—C14—C130.4 (3)F3Ai—K1—P2—F794.2 (3)
C15—N4—C14—C13175.7 (2)F3A—K1—P2—F7−81.8 (3)
C12—N4—C15—C16105.0 (3)F3—K1—P2—F7−76.70 (18)
C14—N4—C15—C16−69.7 (3)F3i—K1—P2—F795.36 (15)
N4—C15—C16—C21−82.8 (3)F7i—K1—P2—F7−178.38 (4)
N4—C15—C16—C1797.3 (3)F5—K1—P2—F7−36.96 (14)
C21—C16—C17—C181.0 (4)F5i—K1—P2—F752.71 (15)
C15—C16—C17—C18−179.0 (3)F5Ai—K1—P2—F7ii−129.4 (3)
C16—C17—C18—C19−1.4 (4)F5A—K1—P2—F7ii138.4 (4)
C17—C18—C19—C201.3 (5)F9—K1—P2—F7ii−54.34 (18)
C18—C19—C20—C21−0.8 (4)F9i—K1—P2—F7ii27.61 (13)
C17—C16—C21—C20−0.6 (4)F3Ai—K1—P2—F7ii−85.8 (3)
C15—C16—C21—C20179.5 (2)F3A—K1—P2—F7ii98.2 (3)
C19—C20—C21—C160.4 (4)F3—K1—P2—F7ii103.30 (18)
F5A—P1—F1—K149.5 (6)F3i—K1—P2—F7ii−84.64 (15)
F2—P1—F1—K1−133.3 (3)F7i—K1—P2—F7ii1.62 (4)
F4—P1—F1—K1136.3 (3)F7—K1—P2—F7ii180.0
F3A—P1—F1—K1−46.9 (5)F5—K1—P2—F7ii143.03 (14)
F3—P1—F1—K1−40.2 (3)F5i—K1—P2—F7ii−127.29 (15)
F1A—P1—F1—K1−162 (4)F5Ai—K1—P2—F8−13.6 (3)
F5—P1—F1—K146.6 (2)F5A—K1—P2—F8−105.8 (4)
F4A—P1—F1—K1141.2 (4)F9—K1—P2—F861.46 (18)
F2A—P1—F1—K1−133.0 (5)F3Ai—K1—P2—F830.0 (3)
F5Ai—K1—F1—P1−99.2 (5)F3A—K1—P2—F8−146.0 (3)
F5A—K1—F1—P1−38.6 (5)F3—K1—P2—F8−140.91 (18)
F9—K1—F1—P167.2 (4)F3i—K1—P2—F831.15 (15)
F9i—K1—F1—P1119.6 (3)F7i—K1—P2—F8117.41 (15)
F3Ai—K1—F1—P1−137.2 (5)F7—K1—P2—F8−64.20 (17)
F3A—K1—F1—P137.1 (5)F5—K1—P2—F8−101.17 (15)
F3—K1—F1—P130.2 (3)F5i—K1—P2—F8−11.50 (15)
F3i—K1—F1—P1−139.1 (2)F5Ai—K1—P2—F8ii166.4 (3)
F7i—K1—F1—P1170.3 (3)F5A—K1—P2—F8ii74.2 (4)
F7—K1—F1—P16.3 (4)F9—K1—P2—F8ii−118.54 (18)
F5—K1—F1—P1−35.15 (18)F9i—K1—P2—F8ii−36.60 (13)
F5i—K1—F1—P1−104.8 (3)F3Ai—K1—P2—F8ii−150.0 (3)
F5A—P1—F3—K1−32.0 (8)F3A—K1—P2—F8ii34.0 (3)
F6A—P1—F3—K1−142.3 (6)F3—K1—P2—F8ii39.09 (18)
F2—P1—F3—K1137.2 (4)F3i—K1—P2—F8ii−148.85 (15)
F1—P1—F3—K142.8 (4)F7i—K1—P2—F8ii−62.59 (15)
F3A—P1—F3—K181 (3)F7—K1—P2—F8ii115.79 (17)
F1A—P1—F3—K153.0 (8)F5—K1—P2—F8ii78.83 (15)
F5—P1—F3—K1−44.9 (3)F5i—K1—P2—F8ii168.50 (15)
F6—P1—F3—K1−132.3 (2)F5A—K1—P2—F9−167.2 (4)
F2A—P1—F3—K1139.5 (5)F9i—K1—P2—F981.94 (16)
F5Ai—K1—F3—P138.3 (4)F3Ai—K1—P2—F9−31.5 (3)
F5A—K1—F3—P122.8 (6)F3A—K1—P2—F9152.5 (3)
F9—K1—F3—P1166.4 (2)F3—K1—P2—F9157.63 (19)
F9i—K1—F3—P1−106.3 (3)F3i—K1—P2—F9−30.31 (15)
F3A—K1—F3—P1−82 (3)F7i—K1—P2—F955.95 (15)
F7i—K1—F3—P1−65.9 (3)F7—K1—P2—F9−125.66 (18)
F7—K1—F3—P1129.8 (3)F5—K1—P2—F9−162.63 (15)
F5—K1—F3—P133.6 (3)F5i—K1—P2—F9−72.96 (16)
F5i—K1—F3—P128.9 (3)F5Ai—K1—P2—F9ii105.0 (3)
F5A—P1—F5—K1−61 (3)F5A—K1—P2—F9ii12.8 (4)
F6A—P1—F5—K1124.6 (7)F9—K1—P2—F9ii180.0
F4—P1—F5—K1−137.7 (3)F9i—K1—P2—F9ii−98.06 (16)
F1—P1—F5—K1−48.1 (2)F3Ai—K1—P2—F9ii148.5 (3)
F3A—P1—F5—K134.7 (6)F3A—K1—P2—F9ii−27.5 (3)
F3—P1—F5—K143.5 (3)F3—K1—P2—F9ii−22.37 (19)
F1A—P1—F5—K1−53.8 (8)F3i—K1—P2—F9ii149.69 (15)
F6—P1—F5—K1131.9 (3)F7i—K1—P2—F9ii−124.05 (15)
F4A—P1—F5—K1−141.6 (6)F7—K1—P2—F9ii54.33 (18)
F5Ai—K1—F5—P1150.9 (5)F5—K1—P2—F9ii17.37 (15)
F5A—K1—F5—P151 (2)F5i—K1—P2—F9ii107.04 (16)
F9—K1—F5—P1−107.2 (2)F8—P2—F7—K1130.58 (12)
F9i—K1—F5—P19.2 (2)F8ii—P2—F7—K1−49.43 (12)
F3Ai—K1—F5—P1153.6 (4)F9—P2—F7—K139.57 (12)
F3A—K1—F5—P1−25.6 (5)F9ii—P2—F7—K1−140.43 (12)
F3—K1—F5—P1−33.0 (2)K1ii—P2—F7—K1180.0
F3i—K1—F5—P1146.5 (2)F5Ai—K1—F7—P2−135.0 (3)
F7i—K1—F5—P158.1 (2)F5A—K1—F7—P2143.2 (3)
F7—K1—F5—P1−112.0 (2)F9—K1—F7—P2−29.90 (10)
F5i—K1—F5—P1143.1 (3)F9i—K1—F7—P232.02 (15)
F5A—P1—F1A—K146.5 (6)F3Ai—K1—F7—P2−87.7 (3)
F6A—P1—F1A—K1−129 (4)F3A—K1—F7—P297.1 (3)
F2—P1—F1A—K1−135.1 (5)F3—K1—F7—P2100.23 (16)
F4—P1—F1A—K1133.8 (4)F3i—K1—F7—P2−89.39 (15)
F1—P1—F1A—K116 (4)F7i—K1—F7—P24.04 (10)
F3A—P1—F1A—K1−48.0 (5)F5—K1—F7—P2145.43 (13)
F3—P1—F1A—K1−43.0 (4)F5i—K1—F7—P2−135.93 (12)
F5—P1—F1A—K145.0 (4)F7—P2—F8—K1ii133.87 (11)
F4A—P1—F1A—K1139.4 (5)F7ii—P2—F8—K1ii−46.13 (11)
F2A—P1—F1A—K1−135.0 (6)F9—P2—F8—K1ii−136.46 (11)
F5Ai—K1—F1A—P1−95.8 (7)F9ii—P2—F8—K1ii43.54 (11)
F5A—K1—F1A—P1−36.6 (6)K1—P2—F8—K1ii180.0
F9—K1—F1A—P172.8 (10)F7—P2—F9—K1−40.56 (13)
F9i—K1—F1A—P1123.3 (7)F7ii—P2—F9—K1139.44 (13)
F3Ai—K1—F1A—P1−135.3 (6)F8—P2—F9—K1−132.19 (13)
F3A—K1—F1A—P138.8 (6)F8ii—P2—F9—K147.81 (13)
F3—K1—F1A—P132.0 (4)K1ii—P2—F9—K1180.0
F3i—K1—F1A—P1−136.9 (5)F5Ai—K1—F9—P2114.3 (4)
F7i—K1—F1A—P1174.7 (8)F5A—K1—F9—P218.6 (5)
F7—K1—F1A—P111.1 (9)F9i—K1—F9—P2−100.15 (13)
F5—K1—F1A—P1−32.8 (4)F3Ai—K1—F9—P2146.5 (3)
F5i—K1—F1A—P1−101.3 (7)F3A—K1—F9—P2−30.1 (3)
F5A—P1—F3A—K1−23.0 (10)F3—K1—F9—P2−23.9 (2)
F6A—P1—F3A—K1−133.1 (7)F3i—K1—F9—P2149.16 (15)
F2—P1—F3A—K1145.8 (6)F7i—K1—F9—P2−140.27 (11)
F1—P1—F3A—K151.1 (6)F7—K1—F9—P229.79 (10)
F3—P1—F3A—K1−90 (3)F5—K1—F9—P223.24 (19)
F1A—P1—F3A—K161.9 (9)
D—H···AD—HH···AD···AD—H···A
C14—H14A···F1iii0.932.453.285 (5)149
C15—H15A···F60.972.513.204 (5)129
C15—H15B···F4iii0.972.513.415 (7)156
C22—H22A···F6iv0.962.423.171 (5)135
Table 1

Selected bond lengths (Å)

Ag1—C122.092 (2)
Ag1—C12.093 (2)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C14—H14A⋯F1i0.932.453.285 (5)149
C15—H15A⋯F60.972.513.204 (5)129
C15—H15B⋯F4i0.972.513.415 (7)156
C22—H22A⋯F6ii0.962.423.171 (5)135

Symmetry codes: (i) ; (ii) .

  8 in total

1.  Stable Carbenes.

Authors:  Didier Bourissou; Olivier Guerret; François P. Gabbaï; Guy Bertrand
Journal:  Chem Rev       Date:  2000-01-12       Impact factor: 60.622

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes.

Authors:  Sriparna Ray; Renu Mohan; Jay K Singh; Manoja K Samantaray; Mobin M Shaikh; Dulal Panda; Prasenjit Ghosh
Journal:  J Am Chem Soc       Date:  2007-11-08       Impact factor: 15.419

4.  1,3-Bis[(3-allyl-imidazol-3-ium-1-yl)meth-yl]benzene bis-(hexa-fluoridophosphate).

Authors:  Rosenani A Haque; Mohammed Z Ghdhayeb; Hassan H Abdallah; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-12-11

5.  3,5-Bis(3-butylimidazolium-1-ylmethyl)toluene bis(hexafluorophosphate).

Authors:  Rosenani A Haque; Abbas Washeel; Siang Guan Teoh; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-13

6.  Synthesis and antimicrobial activity of novel Ag-N-hetero-cyclic carbene complexes.

Authors:  Ilknur Ozdemir; Emine Ozge Ozcan; Selami Günal; Nevin Gürbüz
Journal:  Molecules       Date:  2010-04-08       Impact factor: 4.411

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20

8.  Anticancer Activity of Ag(I) N-Heterocyclic Carbene Complexes Derived from 4,5-Dichloro-1H-Imidazole.

Authors:  Doug A Medvetz; Khadijah M Hindi; Matthew J Panzner; Andrew J Ditto; Yang H Yun; Wiley J Youngs
Journal:  Met Based Drugs       Date:  2008
  8 in total

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