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Acta Cryst. (2011). E67, m1116    [ doi:10.1107/S1600536811026675 ]

Bis[1-benzyl-3-(4-methylphenyl)imidazol-2-ylidene]silver(I) hexafluoridophosphate

K. Huang and D.-B. Qin

Abstract top

The title silver N-heterocyclic carbene compound, [Ag(C17H16N2)2]PF6, crystallizes as a mononuclear salt. The two imidazole rings, which are almost coplanar [maximum deviation from the least squares plane of 0.05 (2) Å], are linked by the Ag atom with a C-Ag-C angle of 178.60 (9)°. In the crystal, C-H...F hydrogen bonds, weak [pi]-[pi] interactions [centroid-centroid distances = 3.921 (1) and 3.813 (3) Å] and C-H...[pi] interactions lead to a supermolecular structure.

Comment top

The discivery of first silver N-heterocyclic carbene (NHC) in 1993 by Arduengo (Arduengo et al., 1993) led to its rapid use in organometallic chemistry (Lin et al., 2009). silver NHCs can be used in various fields such as medical chemistry, Catalysis et al. (Nebioglu et al., 2007; Samantaray et al., 2007). Herein we report the crystal structure of the title silver NHC compound.

In the title compound, the silver(I) atom lies on a non-crystallographic twofold axis. The Ag—C bond lengths are close to literature values (Wang, Xu et al., 2005). The silver coordination geometry is almost linear with a C—Ag—C angle of 178.60 (9) °. The two five membered rings are almost co-planar with C9 showing the maximum deviation from the least squares plane of 0.05 Å. The silver atom is 0.07 Å out of this plane and the C11–C16 and C28–C33 rings make angles of 46.61 ° and 41.77 ° repectively with it.

In the crystal there are C—H···F hydrogen bonds and π–π interactions which contribute to supermolecular structure. (Fig. 2) The π–π interactions are between rings N3/C25/N4/C26/C27 and N1/C8/N2/C9/C10 and rings C11–C16 and C28–C33 with the ring centroids being separated by 3.921 Å and 3.813 Å, respectively. [symmetry code: 1-X,1/2+Y,1/2-Z and 1-X,-1/2+Y,1/2-Z.] In addition C—H···π interactions involving the imidazole and benzene rings are also observed.

Related literature top

For the first silver N-heterocyclic carbene, see: Arduengo et al.(1993). For the role of N-heterocyclic carbene ligands in organometallic chemistry, see: Lin et al. (2009). For applications of silver N-heterocyclic carbenes, see: Nebioglu et al. (2007); Samantaray et al. (2007). For Ag—C bond lengths, see: Wang, Xu et al. (2005). For the synthesis of the title compound, see: Liu et al. (2003); Wang, Song et al. (2005). For a related structure, see: Catalano & Etogo (2007).

Experimental top

The title compound was prepared according to the reported procedures (Liu et al. 2003; Wang, Song et al. 2005). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane and diethyl ether.

Refinement top

H atoms were placed in calculated positions with C—H = 0.95–0.99 Å, and refined in the riding mode with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound. The displacement ellipsoids are drawn at 30% probability level. C-bound H atoms have been omitted For clarity.
[Figure 2] Fig. 2. Crystal packing of the title compound, view down the a axis, showing the cations and anions linked via C—H···F interactions (dashed lines).H-atoms not involved in these interactions have been omitted for clarity.
Bis[1-benzyl-3-(4-methylphenyl)imidazol-2-ylidene]silver(I) hexafluoridophosphate top
Crystal data top
[Ag(C17H16N2)2]PF6F(000) = 1520
Mr = 749.48Dx = 1.560 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.692 (2) ÅCell parameters from 11560 reflections
b = 16.312 (4) Åθ = 1.6–27.9°
c = 20.227 (5) ŵ = 0.75 mm−1
β = 93.469 (3)°T = 113 K
V = 3192.1 (12) Å3Prism, colorless
Z = 40.20 × 0.18 × 0.12 mm
Data collection top
Rigaku Saturn CCD area detector
diffractometer		5636 independent reflections
Radiation source: rotating anode4775 reflections with I > 2σ(I)
multilayerRint = 0.043
Detector resolution: 14.63 pixels mm-1θmax = 25.0°, θmin = 1.6°
ω and φ scansh = −11→7
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)		k = −19→19
Tmin = 0.865, Tmax = 0.916l = −22→24
21677 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0457P)2]
where P = (Fo2 + 2Fc2)/3
5636 reflections(Δ/σ)max = 0.002
417 parametersΔρmax = 1.29 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
[Ag(C17H16N2)2]PF6V = 3192.1 (12) Å3
Mr = 749.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.692 (2) ŵ = 0.75 mm−1
b = 16.312 (4) ÅT = 113 K
c = 20.227 (5) Å0.20 × 0.18 × 0.12 mm
β = 93.469 (3)°
Data collection top
Rigaku Saturn CCD area detector
diffractometer		5636 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)		4775 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.916Rint = 0.043
21677 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.081Δρmax = 1.29 e Å−3
S = 1.01Δρmin = −0.38 e Å−3
5636 reflectionsAbsolute structure: ?
417 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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*/Ueq
Ag10.41572 (2)0.859060 (11)0.816377 (9)0.02055 (8)
N10.2579 (2)1.00527 (12)0.74697 (10)0.0201 (5)
N20.4069 (2)1.04857 (12)0.82125 (10)0.0201 (5)
N30.5671 (2)0.71360 (12)0.88999 (11)0.0218 (5)
N40.4187 (2)0.66895 (13)0.81610 (10)0.0203 (5)
C10.3421 (3)0.91678 (15)0.61584 (14)0.0236 (6)
H10.39710.88910.64930.028*
C20.3847 (3)0.91908 (15)0.55177 (14)0.0269 (6)
H20.46780.89250.54130.032*
C30.3058 (3)0.96022 (16)0.50299 (14)0.0282 (7)
H30.33450.96190.45890.034*
C40.1846 (3)0.99894 (16)0.51871 (13)0.0273 (6)
H40.13071.02770.48550.033*
C50.1421 (3)0.99574 (16)0.58290 (13)0.0237 (6)
H50.05871.02220.59330.028*
C60.2194 (3)0.95459 (14)0.63189 (13)0.0211 (6)
C70.1735 (3)0.95170 (15)0.70193 (13)0.0240 (6)
H7A0.07560.96890.70190.029*
H7B0.18000.89460.71840.029*
C80.3559 (3)0.97862 (15)0.79212 (13)0.0194 (6)
C90.3392 (3)1.11697 (15)0.79473 (13)0.0230 (6)
H90.35561.17240.80740.028*
C100.2466 (3)1.09047 (15)0.74812 (14)0.0248 (6)
H100.18511.12320.72100.030*
C110.5114 (3)1.05048 (15)0.87445 (13)0.0215 (6)
C120.4931 (3)1.10008 (17)0.92862 (14)0.0296 (7)
H120.41311.13350.93020.035*
C130.5936 (3)1.10046 (17)0.98088 (14)0.0320 (7)
H130.58191.13531.01780.038*
C140.7096 (3)1.05160 (17)0.98046 (13)0.0279 (6)
C150.7260 (3)1.00243 (16)0.92519 (13)0.0257 (6)
H150.80520.96830.92400.031*
C160.6293 (3)1.00224 (15)0.87199 (13)0.0232 (6)
H160.64330.96950.83420.028*
C170.8157 (3)1.0520 (2)1.03823 (15)0.0394 (8)
H17A0.85001.10801.04580.059*
H17B0.89291.01611.02840.059*
H17C0.77321.03231.07800.059*
C180.8641 (3)0.77442 (17)0.86335 (14)0.0329 (7)
H180.80720.79990.82940.040*
C191.0014 (3)0.7597 (2)0.85337 (16)0.0423 (8)
H191.03800.77420.81250.051*
C201.0861 (3)0.72373 (19)0.90282 (17)0.0424 (8)
H201.18100.71420.89620.051*
C211.0310 (3)0.70167 (18)0.96223 (16)0.0376 (8)
H211.08820.67690.99640.045*
C220.8923 (3)0.71589 (16)0.97149 (14)0.0284 (7)
H220.85480.70041.01200.034*
C230.8082 (3)0.75253 (15)0.92215 (13)0.0232 (6)
C240.6570 (3)0.76661 (15)0.93234 (13)0.0261 (6)
H24A0.63950.75610.97930.031*
H24B0.63380.82460.92260.031*
C250.4730 (3)0.73940 (15)0.84277 (13)0.0219 (6)
C260.4790 (3)0.60099 (15)0.84766 (13)0.0239 (6)
H260.45820.54510.83820.029*
C270.5712 (3)0.62885 (15)0.89357 (14)0.0250 (6)
H270.62880.59680.92310.030*
C280.3152 (3)0.66399 (15)0.76335 (13)0.0214 (6)
C290.3165 (3)0.71662 (15)0.70946 (13)0.0243 (6)
H290.38850.75580.70670.029*
C300.2120 (3)0.71147 (15)0.65974 (14)0.0284 (7)
H300.21160.74870.62360.034*
C310.1089 (3)0.65370 (15)0.66140 (14)0.0256 (6)
C320.1107 (3)0.59955 (16)0.71508 (14)0.0259 (6)
H320.04130.55860.71650.031*
C330.2115 (3)0.60464 (15)0.76600 (13)0.0229 (6)
H330.21050.56820.80260.027*
C34−0.0037 (3)0.64745 (17)0.60683 (15)0.0359 (7)
H34A−0.06460.69530.60830.054*
H34B−0.05760.59740.61280.054*
H34C0.03780.64550.56390.054*
P10.76650 (7)0.85484 (4)0.67062 (3)0.02175 (17)
F10.84018 (19)0.77564 (9)0.70222 (8)0.0389 (4)
F20.89576 (18)0.86984 (11)0.62716 (9)0.0443 (5)
F30.69599 (18)0.79928 (10)0.61225 (8)0.0374 (4)
F40.63656 (18)0.83735 (13)0.71351 (9)0.0523 (5)
F50.6920 (2)0.93310 (10)0.63843 (9)0.0517 (5)
F60.83605 (18)0.90927 (9)0.72922 (8)0.0357 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.02564 (13)0.01226 (11)0.02389 (13)0.00213 (8)0.00264 (9)0.00104 (8)
N10.0228 (12)0.0150 (10)0.0228 (12)0.0007 (10)0.0041 (10)−0.0013 (9)
N20.0236 (12)0.0145 (11)0.0228 (12)0.0016 (9)0.0050 (10)0.0008 (9)
N30.0234 (12)0.0171 (11)0.0249 (13)0.0034 (10)0.0022 (10)0.0021 (9)
N40.0227 (12)0.0136 (10)0.0248 (13)0.0027 (9)0.0038 (10)0.0031 (9)
C10.0221 (14)0.0163 (12)0.0320 (16)−0.0006 (12)−0.0016 (12)0.0035 (11)
C20.0247 (15)0.0221 (14)0.0346 (17)−0.0020 (12)0.0063 (13)−0.0044 (12)
C30.0301 (16)0.0279 (15)0.0268 (16)−0.0100 (13)0.0018 (13)−0.0051 (12)
C40.0291 (16)0.0268 (14)0.0248 (16)−0.0093 (13)−0.0088 (13)0.0009 (12)
C50.0168 (14)0.0222 (13)0.0315 (16)−0.0028 (12)−0.0027 (12)−0.0027 (12)
C60.0206 (14)0.0147 (12)0.0278 (15)−0.0066 (11)0.0007 (12)−0.0017 (11)
C70.0215 (14)0.0193 (13)0.0310 (16)−0.0040 (12)0.0009 (12)0.0013 (11)
C80.0198 (14)0.0186 (13)0.0204 (14)−0.0005 (11)0.0048 (12)−0.0002 (11)
C90.0262 (15)0.0122 (12)0.0314 (16)0.0034 (12)0.0066 (13)0.0013 (11)
C100.0231 (15)0.0168 (13)0.0349 (17)0.0038 (12)0.0057 (13)0.0049 (11)
C110.0256 (15)0.0175 (13)0.0219 (14)−0.0019 (12)0.0045 (12)0.0015 (11)
C120.0301 (16)0.0281 (15)0.0308 (17)0.0078 (13)0.0041 (14)−0.0043 (12)
C130.0380 (18)0.0334 (16)0.0250 (16)0.0053 (14)0.0048 (14)−0.0066 (13)
C140.0288 (16)0.0313 (15)0.0239 (15)−0.0017 (13)0.0029 (12)0.0043 (12)
C150.0218 (15)0.0225 (14)0.0333 (16)0.0021 (12)0.0067 (13)0.0036 (12)
C160.0257 (15)0.0176 (13)0.0270 (15)−0.0005 (12)0.0073 (12)−0.0030 (11)
C170.0378 (19)0.0473 (19)0.0327 (18)0.0019 (16)−0.0003 (15)0.0002 (14)
C180.0410 (19)0.0330 (16)0.0245 (16)−0.0019 (15)0.0001 (14)0.0027 (12)
C190.042 (2)0.051 (2)0.0350 (19)−0.0101 (17)0.0121 (16)−0.0057 (15)
C200.0267 (17)0.047 (2)0.055 (2)−0.0058 (15)0.0118 (16)−0.0201 (17)
C210.0300 (17)0.0363 (17)0.045 (2)0.0046 (15)−0.0115 (15)−0.0100 (14)
C220.0349 (17)0.0234 (14)0.0265 (16)−0.0014 (13)−0.0008 (13)−0.0017 (12)
C230.0285 (15)0.0143 (12)0.0264 (15)−0.0014 (12)−0.0007 (12)−0.0053 (11)
C240.0328 (16)0.0218 (14)0.0232 (15)0.0033 (13)−0.0010 (13)−0.0025 (11)
C250.0229 (15)0.0191 (13)0.0240 (15)0.0027 (12)0.0039 (12)0.0001 (11)
C260.0263 (15)0.0154 (13)0.0305 (16)0.0058 (12)0.0067 (13)0.0066 (11)
C270.0261 (15)0.0186 (13)0.0307 (16)0.0067 (12)0.0047 (13)0.0050 (11)
C280.0234 (15)0.0153 (12)0.0259 (15)0.0060 (12)0.0045 (12)−0.0019 (11)
C290.0320 (16)0.0148 (12)0.0263 (15)−0.0015 (12)0.0043 (13)0.0002 (11)
C300.0417 (18)0.0171 (13)0.0263 (16)0.0061 (13)0.0015 (14)0.0036 (11)
C310.0282 (16)0.0225 (14)0.0260 (15)0.0076 (13)0.0000 (12)−0.0057 (11)
C320.0266 (15)0.0195 (14)0.0321 (16)0.0012 (12)0.0064 (13)−0.0025 (12)
C330.0257 (15)0.0186 (13)0.0251 (15)0.0014 (12)0.0077 (12)0.0016 (11)
C340.0393 (19)0.0317 (16)0.0362 (19)0.0047 (14)−0.0022 (15)−0.0054 (13)
P10.0225 (4)0.0188 (3)0.0241 (4)−0.0008 (3)0.0027 (3)0.0009 (3)
F10.0516 (11)0.0235 (8)0.0403 (10)0.0065 (8)−0.0081 (9)0.0006 (7)
F20.0345 (10)0.0628 (12)0.0370 (11)−0.0186 (9)0.0119 (8)−0.0025 (9)
F30.0408 (10)0.0368 (9)0.0336 (10)−0.0077 (8)−0.0071 (8)−0.0050 (7)
F40.0329 (11)0.0815 (14)0.0443 (12)−0.0074 (10)0.0168 (9)−0.0011 (10)
F50.0726 (14)0.0287 (9)0.0514 (12)0.0177 (10)−0.0154 (10)0.0024 (8)
F60.0487 (11)0.0246 (8)0.0330 (10)−0.0020 (8)−0.0046 (8)−0.0071 (7)
Geometric parameters (Å, °) top
Ag1—C82.085 (2)C16—H160.9500
Ag1—C252.090 (2)C17—H17A0.9800
N1—C81.349 (3)C17—H17B0.9800
N1—C101.395 (3)C17—H17C0.9800
N1—C71.474 (3)C18—C191.380 (4)
N2—C81.363 (3)C18—C231.383 (4)
N2—C91.386 (3)C18—H180.9500
N2—C111.433 (3)C19—C201.385 (4)
N3—C251.348 (3)C19—H190.9500
N3—C271.385 (3)C20—C211.392 (4)
N3—C241.466 (3)C20—H200.9500
N4—C251.362 (3)C21—C221.387 (4)
N4—C261.390 (3)C21—H210.9500
N4—C281.422 (3)C22—C231.385 (4)
C1—C21.384 (4)C22—H220.9500
C1—C61.395 (4)C23—C241.510 (4)
C1—H10.9500C24—H24A0.9900
C2—C31.385 (4)C24—H24B0.9900
C2—H20.9500C26—C271.329 (4)
C3—C41.387 (4)C26—H260.9500
C3—H30.9500C27—H270.9500
C4—C51.387 (4)C28—C291.388 (4)
C4—H40.9500C28—C331.399 (4)
C5—C61.380 (4)C29—C301.386 (4)
C5—H50.9500C29—H290.9500
C6—C71.511 (3)C30—C311.376 (4)
C7—H7A0.9900C30—H300.9500
C7—H7B0.9900C31—C321.399 (4)
C9—C101.333 (4)C31—C341.508 (4)
C9—H90.9500C32—C331.378 (4)
C10—H100.9500C32—H320.9500
C11—C121.382 (4)C33—H330.9500
C11—C161.391 (4)C34—H34A0.9800
C12—C131.393 (4)C34—H34B0.9800
C12—H120.9500C34—H34C0.9800
C13—C141.379 (4)P1—F51.5867 (17)
C13—H130.9500P1—F11.5913 (17)
C14—C151.393 (4)P1—F21.5923 (18)
C14—C171.509 (4)P1—F61.5971 (16)
C15—C161.384 (4)P1—F41.5977 (18)
C15—H150.9500P1—F31.6077 (17)
C8—Ag1—C25178.60 (9)C19—C18—H18119.6
C8—N1—C10111.3 (2)C23—C18—H18119.6
C8—N1—C7124.7 (2)C18—C19—C20120.2 (3)
C10—N1—C7124.1 (2)C18—C19—H19119.9
C8—N2—C9110.8 (2)C20—C19—H19119.9
C8—N2—C11124.4 (2)C19—C20—C21119.4 (3)
C9—N2—C11124.7 (2)C19—C20—H20120.3
C25—N3—C27111.4 (2)C21—C20—H20120.3
C25—N3—C24125.6 (2)C22—C21—C20119.9 (3)
C27—N3—C24123.0 (2)C22—C21—H21120.0
C25—N4—C26110.5 (2)C20—C21—H21120.0
C25—N4—C28125.7 (2)C23—C22—C21120.5 (3)
C26—N4—C28123.9 (2)C23—C22—H22119.8
C2—C1—C6120.8 (2)C21—C22—H22119.8
C2—C1—H1119.6C18—C23—C22119.1 (3)
C6—C1—H1119.6C18—C23—C24120.8 (2)
C1—C2—C3119.8 (3)C22—C23—C24120.1 (2)
C1—C2—H2120.1N3—C24—C23112.2 (2)
C3—C2—H2120.1N3—C24—H24A109.2
C2—C3—C4119.7 (3)C23—C24—H24A109.2
C2—C3—H3120.1N3—C24—H24B109.2
C4—C3—H3120.1C23—C24—H24B109.2
C5—C4—C3120.1 (3)H24A—C24—H24B107.9
C5—C4—H4120.0N3—C25—N4104.2 (2)
C3—C4—H4120.0N3—C25—Ag1129.10 (18)
C6—C5—C4120.7 (3)N4—C25—Ag1126.64 (19)
C6—C5—H5119.6C27—C26—N4107.1 (2)
C4—C5—H5119.6C27—C26—H26126.4
C5—C6—C1118.8 (2)N4—C26—H26126.4
C5—C6—C7120.7 (2)C26—C27—N3106.8 (2)
C1—C6—C7120.5 (2)C26—C27—H27126.6
N1—C7—C6112.2 (2)N3—C27—H27126.6
N1—C7—H7A109.2C29—C28—C33119.9 (3)
C6—C7—H7A109.2C29—C28—N4120.9 (2)
N1—C7—H7B109.2C33—C28—N4119.1 (2)
C6—C7—H7B109.2C30—C29—C28119.4 (3)
H7A—C7—H7B107.9C30—C29—H29120.3
N1—C8—N2104.2 (2)C28—C29—H29120.3
N1—C8—Ag1129.43 (18)C31—C30—C29121.6 (3)
N2—C8—Ag1126.36 (19)C31—C30—H30119.2
C10—C9—N2107.2 (2)C29—C30—H30119.2
C10—C9—H9126.4C30—C31—C32118.5 (3)
N2—C9—H9126.4C30—C31—C34121.6 (3)
C9—C10—N1106.5 (2)C32—C31—C34120.0 (3)
C9—C10—H10126.7C33—C32—C31121.1 (3)
N1—C10—H10126.7C33—C32—H32119.4
C12—C11—C16120.3 (3)C31—C32—H32119.4
C12—C11—N2119.3 (2)C32—C33—C28119.4 (2)
C16—C11—N2120.4 (2)C32—C33—H33120.3
C11—C12—C13119.2 (3)C28—C33—H33120.3
C11—C12—H12120.4C31—C34—H34A109.5
C13—C12—H12120.4C31—C34—H34B109.5
C14—C13—C12121.7 (3)H34A—C34—H34B109.5
C14—C13—H13119.1C31—C34—H34C109.5
C12—C13—H13119.1H34A—C34—H34C109.5
C13—C14—C15118.0 (3)H34B—C34—H34C109.5
C13—C14—C17120.7 (3)F5—P1—F1179.27 (11)
C15—C14—C17121.3 (3)F5—P1—F290.20 (11)
C16—C15—C14121.4 (3)F1—P1—F289.85 (10)
C16—C15—H15119.3F5—P1—F691.05 (9)
C14—C15—H15119.3F1—P1—F689.67 (9)
C15—C16—C11119.4 (2)F2—P1—F690.77 (10)
C15—C16—H16120.3F5—P1—F490.71 (11)
C11—C16—H16120.3F1—P1—F489.21 (11)
C14—C17—H17A109.5F2—P1—F4178.48 (11)
C14—C17—H17B109.5F6—P1—F490.43 (10)
H17A—C17—H17B109.5F5—P1—F389.41 (10)
C14—C17—H17C109.5F1—P1—F389.87 (9)
H17A—C17—H17C109.5F2—P1—F389.71 (10)
H17B—C17—H17C109.5F6—P1—F3179.34 (10)
C19—C18—C23120.8 (3)F4—P1—F389.09 (10)
C6—C1—C2—C30.8 (4)C23—C18—C19—C20−1.0 (5)
C1—C2—C3—C40.1 (4)C18—C19—C20—C210.8 (5)
C2—C3—C4—C5−0.6 (4)C19—C20—C21—C22−0.1 (4)
C3—C4—C5—C60.3 (4)C20—C21—C22—C23−0.5 (4)
C4—C5—C6—C10.6 (4)C19—C18—C23—C220.4 (4)
C4—C5—C6—C7179.5 (2)C19—C18—C23—C24−178.3 (3)
C2—C1—C6—C5−1.1 (4)C21—C22—C23—C180.3 (4)
C2—C1—C6—C7179.9 (2)C21—C22—C23—C24179.1 (2)
C8—N1—C7—C6−104.8 (3)C25—N3—C24—C23−117.8 (3)
C10—N1—C7—C675.0 (3)C27—N3—C24—C2361.1 (3)
C5—C6—C7—N1−106.0 (3)C18—C23—C24—N368.3 (3)
C1—C6—C7—N172.9 (3)C22—C23—C24—N3−110.4 (3)
C10—N1—C8—N2−0.5 (3)C27—N3—C25—N4−0.6 (3)
C7—N1—C8—N2179.3 (2)C24—N3—C25—N4178.4 (2)
C10—N1—C8—Ag1177.56 (18)C27—N3—C25—Ag1177.84 (19)
C7—N1—C8—Ag1−2.6 (4)C24—N3—C25—Ag1−3.1 (4)
C9—N2—C8—N10.9 (3)C26—N4—C25—N30.6 (3)
C11—N2—C8—N1177.8 (2)C28—N4—C25—N3−179.3 (2)
C9—N2—C8—Ag1−177.31 (17)C26—N4—C25—Ag1−177.89 (17)
C11—N2—C8—Ag1−0.4 (3)C28—N4—C25—Ag12.2 (4)
C25—Ag1—C8—N1−103 (4)C8—Ag1—C25—N3−75 (4)
C25—Ag1—C8—N275 (4)C8—Ag1—C25—N4103 (4)
C8—N2—C9—C10−0.9 (3)C25—N4—C26—C27−0.4 (3)
C11—N2—C9—C10−177.8 (2)C28—N4—C26—C27179.5 (2)
N2—C9—C10—N10.5 (3)N4—C26—C27—N30.0 (3)
C8—N1—C10—C90.0 (3)C25—N3—C27—C260.4 (3)
C7—N1—C10—C9−179.8 (2)C24—N3—C27—C26−178.7 (2)
C8—N2—C11—C12−133.5 (3)C25—N4—C28—C2940.1 (4)
C9—N2—C11—C1243.0 (4)C26—N4—C28—C29−139.7 (3)
C8—N2—C11—C1645.7 (3)C25—N4—C28—C33−140.4 (3)
C9—N2—C11—C16−137.7 (3)C26—N4—C28—C3339.8 (3)
C16—C11—C12—C13−0.6 (4)C33—C28—C29—C302.1 (4)
N2—C11—C12—C13178.7 (2)N4—C28—C29—C30−178.4 (2)
C11—C12—C13—C14−1.1 (4)C28—C29—C30—C31−2.0 (4)
C12—C13—C14—C151.4 (4)C29—C30—C31—C320.3 (4)
C12—C13—C14—C17−178.9 (3)C29—C30—C31—C34−179.2 (3)
C13—C14—C15—C160.1 (4)C30—C31—C32—C331.3 (4)
C17—C14—C15—C16−179.7 (3)C34—C31—C32—C33−179.2 (2)
C14—C15—C16—C11−1.7 (4)C31—C32—C33—C28−1.2 (4)
C12—C11—C16—C152.0 (4)C29—C28—C33—C32−0.6 (4)
N2—C11—C16—C15−177.3 (2)N4—C28—C33—C32179.9 (2)
Hydrogen-bond geometry (Å, °) top
Cg3 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C9—H9···F1i0.952.543.120 (6)119
C26—H26···F5ii0.952.403.222 (1)144
C34—H34A···F1iii0.982.533.276 (8)133
C27—H27···Cg3ii0.952.503.295 (1)140
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg3 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C9—H9···F1i0.952.543.120 (6)119
C26—H26···F5ii0.952.403.222 (1)144
C34—H34A···F1iii0.982.533.276 (8)133
C27—H27···Cg3ii0.952.503.295 (1)140
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, y, z.
references
References top

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