Bis[1-benzyl-3-(4-methyl-phen-yl)imidazol-2-yl-idene]silver(I) hexa-fluorido-phosphate.

The title silver N-heterocyclic carbene compound, [Ag(C(17)H(16)N(2))(2)]PF(6), 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 π-π inter-actions [centroid-centroid distances = 3.921 (1) and 3.813 (3) Å] and C-H⋯π inter-actions lead to a supermolecular structure.

Related literature

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

Crystal data

[Ag(C17H16N2)2]PF6

M = 749.48

Monoclinic,

a = 9.692 (2) Å

b = 16.312 (4) Å

c = 20.227 (5) Å

β = 93.469 (3)°

V = 3192.1 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T min = 0.865, T max = 0.916

21677 measured reflections

5636 independent reflections

4775 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.01

5636 reflections

417 parameters

H-atom parameters constrained

Δρmax = 1.29 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026675/qm2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026675/qm2012Isup2.hkl

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

[Ag(C17H16N2)2]PF6	F(000) = 1520
Mr = 749.48	Dx = 1.560 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.692 (2) Å	Cell parameters from 11560 reflections
b = 16.312 (4) Å	θ = 1.6–27.9°
c = 20.227 (5) Å	µ = 0.75 mm−1
β = 93.469 (3)°	T = 113 K
V = 3192.1 (12) Å3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.12 mm

Rigaku Saturn CCD area detector diffractometer	5636 independent reflections
Radiation source: rotating anode	4775 reflections with I > 2σ(I)
multilayer	Rint = 0.043
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 1.6°
ω and φ scans	h = −11→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −19→19
Tmin = 0.865, Tmax = 0.916	l = −22→24
21677 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-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 parameters	Δρmax = 1.29 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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
Ag1	0.41572 (2)	0.859060 (11)	0.816377 (9)	0.02055 (8)
N1	0.2579 (2)	1.00527 (12)	0.74697 (10)	0.0201 (5)
N2	0.4069 (2)	1.04857 (12)	0.82125 (10)	0.0201 (5)
N3	0.5671 (2)	0.71360 (12)	0.88999 (11)	0.0218 (5)
N4	0.4187 (2)	0.66895 (13)	0.81610 (10)	0.0203 (5)
C1	0.3421 (3)	0.91678 (15)	0.61584 (14)	0.0236 (6)
H1	0.3971	0.8891	0.6493	0.028*
C2	0.3847 (3)	0.91908 (15)	0.55177 (14)	0.0269 (6)
H2	0.4678	0.8925	0.5413	0.032*
C3	0.3058 (3)	0.96022 (16)	0.50299 (14)	0.0282 (7)
H3	0.3345	0.9619	0.4589	0.034*
C4	0.1846 (3)	0.99894 (16)	0.51871 (13)	0.0273 (6)
H4	0.1307	1.0277	0.4855	0.033*
C5	0.1421 (3)	0.99574 (16)	0.58290 (13)	0.0237 (6)
H5	0.0587	1.0222	0.5933	0.028*
C6	0.2194 (3)	0.95459 (14)	0.63189 (13)	0.0211 (6)
C7	0.1735 (3)	0.95170 (15)	0.70193 (13)	0.0240 (6)
H7A	0.0756	0.9689	0.7019	0.029*
H7B	0.1800	0.8946	0.7184	0.029*
C8	0.3559 (3)	0.97862 (15)	0.79212 (13)	0.0194 (6)
C9	0.3392 (3)	1.11697 (15)	0.79473 (13)	0.0230 (6)
H9	0.3556	1.1724	0.8074	0.028*
C10	0.2466 (3)	1.09047 (15)	0.74812 (14)	0.0248 (6)
H10	0.1851	1.1232	0.7210	0.030*
C11	0.5114 (3)	1.05048 (15)	0.87445 (13)	0.0215 (6)
C12	0.4931 (3)	1.10008 (17)	0.92862 (14)	0.0296 (7)
H12	0.4131	1.1335	0.9302	0.035*
C13	0.5936 (3)	1.10046 (17)	0.98088 (14)	0.0320 (7)
H13	0.5819	1.1353	1.0178	0.038*
C14	0.7096 (3)	1.05160 (17)	0.98046 (13)	0.0279 (6)
C15	0.7260 (3)	1.00243 (16)	0.92519 (13)	0.0257 (6)
H15	0.8052	0.9683	0.9240	0.031*
C16	0.6293 (3)	1.00224 (15)	0.87199 (13)	0.0232 (6)
H16	0.6433	0.9695	0.8342	0.028*
C17	0.8157 (3)	1.0520 (2)	1.03823 (15)	0.0394 (8)
H17A	0.8500	1.1080	1.0458	0.059*
H17B	0.8929	1.0161	1.0284	0.059*
H17C	0.7732	1.0323	1.0780	0.059*
C18	0.8641 (3)	0.77442 (17)	0.86335 (14)	0.0329 (7)
H18	0.8072	0.7999	0.8294	0.040*
C19	1.0014 (3)	0.7597 (2)	0.85337 (16)	0.0423 (8)
H19	1.0380	0.7742	0.8125	0.051*
C20	1.0861 (3)	0.72373 (19)	0.90282 (17)	0.0424 (8)
H20	1.1810	0.7142	0.8962	0.051*
C21	1.0310 (3)	0.70167 (18)	0.96223 (16)	0.0376 (8)
H21	1.0882	0.6769	0.9964	0.045*
C22	0.8923 (3)	0.71589 (16)	0.97149 (14)	0.0284 (7)
H22	0.8548	0.7004	1.0120	0.034*
C23	0.8082 (3)	0.75253 (15)	0.92215 (13)	0.0232 (6)
C24	0.6570 (3)	0.76661 (15)	0.93234 (13)	0.0261 (6)
H24A	0.6395	0.7561	0.9793	0.031*
H24B	0.6338	0.8246	0.9226	0.031*
C25	0.4730 (3)	0.73940 (15)	0.84277 (13)	0.0219 (6)
C26	0.4790 (3)	0.60099 (15)	0.84766 (13)	0.0239 (6)
H26	0.4582	0.5451	0.8382	0.029*
C27	0.5712 (3)	0.62885 (15)	0.89357 (14)	0.0250 (6)
H27	0.6288	0.5968	0.9231	0.030*
C28	0.3152 (3)	0.66399 (15)	0.76335 (13)	0.0214 (6)
C29	0.3165 (3)	0.71662 (15)	0.70946 (13)	0.0243 (6)
H29	0.3885	0.7558	0.7067	0.029*
C30	0.2120 (3)	0.71147 (15)	0.65974 (14)	0.0284 (7)
H30	0.2116	0.7487	0.6236	0.034*
C31	0.1089 (3)	0.65370 (15)	0.66140 (14)	0.0256 (6)
C32	0.1107 (3)	0.59955 (16)	0.71508 (14)	0.0259 (6)
H32	0.0413	0.5586	0.7165	0.031*
C33	0.2115 (3)	0.60464 (15)	0.76600 (13)	0.0229 (6)
H33	0.2105	0.5682	0.8026	0.027*
C34	−0.0037 (3)	0.64745 (17)	0.60683 (15)	0.0359 (7)
H34A	−0.0646	0.6953	0.6083	0.054*
H34B	−0.0576	0.5974	0.6128	0.054*
H34C	0.0378	0.6455	0.5639	0.054*
P1	0.76650 (7)	0.85484 (4)	0.67062 (3)	0.02175 (17)
F1	0.84018 (19)	0.77564 (9)	0.70222 (8)	0.0389 (4)
F2	0.89576 (18)	0.86984 (11)	0.62716 (9)	0.0443 (5)
F3	0.69599 (18)	0.79928 (10)	0.61225 (8)	0.0374 (4)
F4	0.63656 (18)	0.83735 (13)	0.71351 (9)	0.0523 (5)
F5	0.6920 (2)	0.93310 (10)	0.63843 (9)	0.0517 (5)
F6	0.83605 (18)	0.90927 (9)	0.72922 (8)	0.0357 (4)

	U11	U22	U33	U12	U13	U23
Ag1	0.02564 (13)	0.01226 (11)	0.02389 (13)	0.00213 (8)	0.00264 (9)	0.00104 (8)
N1	0.0228 (12)	0.0150 (10)	0.0228 (12)	0.0007 (10)	0.0041 (10)	−0.0013 (9)
N2	0.0236 (12)	0.0145 (11)	0.0228 (12)	0.0016 (9)	0.0050 (10)	0.0008 (9)
N3	0.0234 (12)	0.0171 (11)	0.0249 (13)	0.0034 (10)	0.0022 (10)	0.0021 (9)
N4	0.0227 (12)	0.0136 (10)	0.0248 (13)	0.0027 (9)	0.0038 (10)	0.0031 (9)
C1	0.0221 (14)	0.0163 (12)	0.0320 (16)	−0.0006 (12)	−0.0016 (12)	0.0035 (11)
C2	0.0247 (15)	0.0221 (14)	0.0346 (17)	−0.0020 (12)	0.0063 (13)	−0.0044 (12)
C3	0.0301 (16)	0.0279 (15)	0.0268 (16)	−0.0100 (13)	0.0018 (13)	−0.0051 (12)
C4	0.0291 (16)	0.0268 (14)	0.0248 (16)	−0.0093 (13)	−0.0088 (13)	0.0009 (12)
C5	0.0168 (14)	0.0222 (13)	0.0315 (16)	−0.0028 (12)	−0.0027 (12)	−0.0027 (12)
C6	0.0206 (14)	0.0147 (12)	0.0278 (15)	−0.0066 (11)	0.0007 (12)	−0.0017 (11)
C7	0.0215 (14)	0.0193 (13)	0.0310 (16)	−0.0040 (12)	0.0009 (12)	0.0013 (11)
C8	0.0198 (14)	0.0186 (13)	0.0204 (14)	−0.0005 (11)	0.0048 (12)	−0.0002 (11)
C9	0.0262 (15)	0.0122 (12)	0.0314 (16)	0.0034 (12)	0.0066 (13)	0.0013 (11)
C10	0.0231 (15)	0.0168 (13)	0.0349 (17)	0.0038 (12)	0.0057 (13)	0.0049 (11)
C11	0.0256 (15)	0.0175 (13)	0.0219 (14)	−0.0019 (12)	0.0045 (12)	0.0015 (11)
C12	0.0301 (16)	0.0281 (15)	0.0308 (17)	0.0078 (13)	0.0041 (14)	−0.0043 (12)
C13	0.0380 (18)	0.0334 (16)	0.0250 (16)	0.0053 (14)	0.0048 (14)	−0.0066 (13)
C14	0.0288 (16)	0.0313 (15)	0.0239 (15)	−0.0017 (13)	0.0029 (12)	0.0043 (12)
C15	0.0218 (15)	0.0225 (14)	0.0333 (16)	0.0021 (12)	0.0067 (13)	0.0036 (12)
C16	0.0257 (15)	0.0176 (13)	0.0270 (15)	−0.0005 (12)	0.0073 (12)	−0.0030 (11)
C17	0.0378 (19)	0.0473 (19)	0.0327 (18)	0.0019 (16)	−0.0003 (15)	0.0002 (14)
C18	0.0410 (19)	0.0330 (16)	0.0245 (16)	−0.0019 (15)	0.0001 (14)	0.0027 (12)
C19	0.042 (2)	0.051 (2)	0.0350 (19)	−0.0101 (17)	0.0121 (16)	−0.0057 (15)
C20	0.0267 (17)	0.047 (2)	0.055 (2)	−0.0058 (15)	0.0118 (16)	−0.0201 (17)
C21	0.0300 (17)	0.0363 (17)	0.045 (2)	0.0046 (15)	−0.0115 (15)	−0.0100 (14)
C22	0.0349 (17)	0.0234 (14)	0.0265 (16)	−0.0014 (13)	−0.0008 (13)	−0.0017 (12)
C23	0.0285 (15)	0.0143 (12)	0.0264 (15)	−0.0014 (12)	−0.0007 (12)	−0.0053 (11)
C24	0.0328 (16)	0.0218 (14)	0.0232 (15)	0.0033 (13)	−0.0010 (13)	−0.0025 (11)
C25	0.0229 (15)	0.0191 (13)	0.0240 (15)	0.0027 (12)	0.0039 (12)	0.0001 (11)
C26	0.0263 (15)	0.0154 (13)	0.0305 (16)	0.0058 (12)	0.0067 (13)	0.0066 (11)
C27	0.0261 (15)	0.0186 (13)	0.0307 (16)	0.0067 (12)	0.0047 (13)	0.0050 (11)
C28	0.0234 (15)	0.0153 (12)	0.0259 (15)	0.0060 (12)	0.0045 (12)	−0.0019 (11)
C29	0.0320 (16)	0.0148 (12)	0.0263 (15)	−0.0015 (12)	0.0043 (13)	0.0002 (11)
C30	0.0417 (18)	0.0171 (13)	0.0263 (16)	0.0061 (13)	0.0015 (14)	0.0036 (11)
C31	0.0282 (16)	0.0225 (14)	0.0260 (15)	0.0076 (13)	0.0000 (12)	−0.0057 (11)
C32	0.0266 (15)	0.0195 (14)	0.0321 (16)	0.0012 (12)	0.0064 (13)	−0.0025 (12)
C33	0.0257 (15)	0.0186 (13)	0.0251 (15)	0.0014 (12)	0.0077 (12)	0.0016 (11)
C34	0.0393 (19)	0.0317 (16)	0.0362 (19)	0.0047 (14)	−0.0022 (15)	−0.0054 (13)
P1	0.0225 (4)	0.0188 (3)	0.0241 (4)	−0.0008 (3)	0.0027 (3)	0.0009 (3)
F1	0.0516 (11)	0.0235 (8)	0.0403 (10)	0.0065 (8)	−0.0081 (9)	0.0006 (7)
F2	0.0345 (10)	0.0628 (12)	0.0370 (11)	−0.0186 (9)	0.0119 (8)	−0.0025 (9)
F3	0.0408 (10)	0.0368 (9)	0.0336 (10)	−0.0077 (8)	−0.0071 (8)	−0.0050 (7)
F4	0.0329 (11)	0.0815 (14)	0.0443 (12)	−0.0074 (10)	0.0168 (9)	−0.0011 (10)
F5	0.0726 (14)	0.0287 (9)	0.0514 (12)	0.0177 (10)	−0.0154 (10)	0.0024 (8)
F6	0.0487 (11)	0.0246 (8)	0.0330 (10)	−0.0020 (8)	−0.0046 (8)	−0.0071 (7)

Ag1—C8	2.085 (2)	C16—H16	0.9500
Ag1—C25	2.090 (2)	C17—H17A	0.9800
N1—C8	1.349 (3)	C17—H17B	0.9800
N1—C10	1.395 (3)	C17—H17C	0.9800
N1—C7	1.474 (3)	C18—C19	1.380 (4)
N2—C8	1.363 (3)	C18—C23	1.383 (4)
N2—C9	1.386 (3)	C18—H18	0.9500
N2—C11	1.433 (3)	C19—C20	1.385 (4)
N3—C25	1.348 (3)	C19—H19	0.9500
N3—C27	1.385 (3)	C20—C21	1.392 (4)
N3—C24	1.466 (3)	C20—H20	0.9500
N4—C25	1.362 (3)	C21—C22	1.387 (4)
N4—C26	1.390 (3)	C21—H21	0.9500
N4—C28	1.422 (3)	C22—C23	1.385 (4)
C1—C2	1.384 (4)	C22—H22	0.9500
C1—C6	1.395 (4)	C23—C24	1.510 (4)
C1—H1	0.9500	C24—H24A	0.9900
C2—C3	1.385 (4)	C24—H24B	0.9900
C2—H2	0.9500	C26—C27	1.329 (4)
C3—C4	1.387 (4)	C26—H26	0.9500
C3—H3	0.9500	C27—H27	0.9500
C4—C5	1.387 (4)	C28—C29	1.388 (4)
C4—H4	0.9500	C28—C33	1.399 (4)
C5—C6	1.380 (4)	C29—C30	1.386 (4)
C5—H5	0.9500	C29—H29	0.9500
C6—C7	1.511 (3)	C30—C31	1.376 (4)
C7—H7A	0.9900	C30—H30	0.9500
C7—H7B	0.9900	C31—C32	1.399 (4)
C9—C10	1.333 (4)	C31—C34	1.508 (4)
C9—H9	0.9500	C32—C33	1.378 (4)
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.382 (4)	C33—H33	0.9500
C11—C16	1.391 (4)	C34—H34A	0.9800
C12—C13	1.393 (4)	C34—H34B	0.9800
C12—H12	0.9500	C34—H34C	0.9800
C13—C14	1.379 (4)	P1—F5	1.5867 (17)
C13—H13	0.9500	P1—F1	1.5913 (17)
C14—C15	1.393 (4)	P1—F2	1.5923 (18)
C14—C17	1.509 (4)	P1—F6	1.5971 (16)
C15—C16	1.384 (4)	P1—F4	1.5977 (18)
C15—H15	0.9500	P1—F3	1.6077 (17)
C8—Ag1—C25	178.60 (9)	C19—C18—H18	119.6
C8—N1—C10	111.3 (2)	C23—C18—H18	119.6
C8—N1—C7	124.7 (2)	C18—C19—C20	120.2 (3)
C10—N1—C7	124.1 (2)	C18—C19—H19	119.9
C8—N2—C9	110.8 (2)	C20—C19—H19	119.9
C8—N2—C11	124.4 (2)	C19—C20—C21	119.4 (3)
C9—N2—C11	124.7 (2)	C19—C20—H20	120.3
C25—N3—C27	111.4 (2)	C21—C20—H20	120.3
C25—N3—C24	125.6 (2)	C22—C21—C20	119.9 (3)
C27—N3—C24	123.0 (2)	C22—C21—H21	120.0
C25—N4—C26	110.5 (2)	C20—C21—H21	120.0
C25—N4—C28	125.7 (2)	C23—C22—C21	120.5 (3)
C26—N4—C28	123.9 (2)	C23—C22—H22	119.8
C2—C1—C6	120.8 (2)	C21—C22—H22	119.8
C2—C1—H1	119.6	C18—C23—C22	119.1 (3)
C6—C1—H1	119.6	C18—C23—C24	120.8 (2)
C1—C2—C3	119.8 (3)	C22—C23—C24	120.1 (2)
C1—C2—H2	120.1	N3—C24—C23	112.2 (2)
C3—C2—H2	120.1	N3—C24—H24A	109.2
C2—C3—C4	119.7 (3)	C23—C24—H24A	109.2
C2—C3—H3	120.1	N3—C24—H24B	109.2
C4—C3—H3	120.1	C23—C24—H24B	109.2
C5—C4—C3	120.1 (3)	H24A—C24—H24B	107.9
C5—C4—H4	120.0	N3—C25—N4	104.2 (2)
C3—C4—H4	120.0	N3—C25—Ag1	129.10 (18)
C6—C5—C4	120.7 (3)	N4—C25—Ag1	126.64 (19)
C6—C5—H5	119.6	C27—C26—N4	107.1 (2)
C4—C5—H5	119.6	C27—C26—H26	126.4
C5—C6—C1	118.8 (2)	N4—C26—H26	126.4
C5—C6—C7	120.7 (2)	C26—C27—N3	106.8 (2)
C1—C6—C7	120.5 (2)	C26—C27—H27	126.6
N1—C7—C6	112.2 (2)	N3—C27—H27	126.6
N1—C7—H7A	109.2	C29—C28—C33	119.9 (3)
C6—C7—H7A	109.2	C29—C28—N4	120.9 (2)
N1—C7—H7B	109.2	C33—C28—N4	119.1 (2)
C6—C7—H7B	109.2	C30—C29—C28	119.4 (3)
H7A—C7—H7B	107.9	C30—C29—H29	120.3
N1—C8—N2	104.2 (2)	C28—C29—H29	120.3
N1—C8—Ag1	129.43 (18)	C31—C30—C29	121.6 (3)
N2—C8—Ag1	126.36 (19)	C31—C30—H30	119.2
C10—C9—N2	107.2 (2)	C29—C30—H30	119.2
C10—C9—H9	126.4	C30—C31—C32	118.5 (3)
N2—C9—H9	126.4	C30—C31—C34	121.6 (3)
C9—C10—N1	106.5 (2)	C32—C31—C34	120.0 (3)
C9—C10—H10	126.7	C33—C32—C31	121.1 (3)
N1—C10—H10	126.7	C33—C32—H32	119.4
C12—C11—C16	120.3 (3)	C31—C32—H32	119.4
C12—C11—N2	119.3 (2)	C32—C33—C28	119.4 (2)
C16—C11—N2	120.4 (2)	C32—C33—H33	120.3
C11—C12—C13	119.2 (3)	C28—C33—H33	120.3
C11—C12—H12	120.4	C31—C34—H34A	109.5
C13—C12—H12	120.4	C31—C34—H34B	109.5
C14—C13—C12	121.7 (3)	H34A—C34—H34B	109.5
C14—C13—H13	119.1	C31—C34—H34C	109.5
C12—C13—H13	119.1	H34A—C34—H34C	109.5
C13—C14—C15	118.0 (3)	H34B—C34—H34C	109.5
C13—C14—C17	120.7 (3)	F5—P1—F1	179.27 (11)
C15—C14—C17	121.3 (3)	F5—P1—F2	90.20 (11)
C16—C15—C14	121.4 (3)	F1—P1—F2	89.85 (10)
C16—C15—H15	119.3	F5—P1—F6	91.05 (9)
C14—C15—H15	119.3	F1—P1—F6	89.67 (9)
C15—C16—C11	119.4 (2)	F2—P1—F6	90.77 (10)
C15—C16—H16	120.3	F5—P1—F4	90.71 (11)
C11—C16—H16	120.3	F1—P1—F4	89.21 (11)
C14—C17—H17A	109.5	F2—P1—F4	178.48 (11)
C14—C17—H17B	109.5	F6—P1—F4	90.43 (10)
H17A—C17—H17B	109.5	F5—P1—F3	89.41 (10)
C14—C17—H17C	109.5	F1—P1—F3	89.87 (9)
H17A—C17—H17C	109.5	F2—P1—F3	89.71 (10)
H17B—C17—H17C	109.5	F6—P1—F3	179.34 (10)
C19—C18—C23	120.8 (3)	F4—P1—F3	89.09 (10)
C6—C1—C2—C3	0.8 (4)	C23—C18—C19—C20	−1.0 (5)
C1—C2—C3—C4	0.1 (4)	C18—C19—C20—C21	0.8 (5)
C2—C3—C4—C5	−0.6 (4)	C19—C20—C21—C22	−0.1 (4)
C3—C4—C5—C6	0.3 (4)	C20—C21—C22—C23	−0.5 (4)
C4—C5—C6—C1	0.6 (4)	C19—C18—C23—C22	0.4 (4)
C4—C5—C6—C7	179.5 (2)	C19—C18—C23—C24	−178.3 (3)
C2—C1—C6—C5	−1.1 (4)	C21—C22—C23—C18	0.3 (4)
C2—C1—C6—C7	179.9 (2)	C21—C22—C23—C24	179.1 (2)
C8—N1—C7—C6	−104.8 (3)	C25—N3—C24—C23	−117.8 (3)
C10—N1—C7—C6	75.0 (3)	C27—N3—C24—C23	61.1 (3)
C5—C6—C7—N1	−106.0 (3)	C18—C23—C24—N3	68.3 (3)
C1—C6—C7—N1	72.9 (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—N2	179.3 (2)	C24—N3—C25—N4	178.4 (2)
C10—N1—C8—Ag1	177.56 (18)	C27—N3—C25—Ag1	177.84 (19)
C7—N1—C8—Ag1	−2.6 (4)	C24—N3—C25—Ag1	−3.1 (4)
C9—N2—C8—N1	0.9 (3)	C26—N4—C25—N3	0.6 (3)
C11—N2—C8—N1	177.8 (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—Ag1	2.2 (4)
C25—Ag1—C8—N1	−103 (4)	C8—Ag1—C25—N3	−75 (4)
C25—Ag1—C8—N2	75 (4)	C8—Ag1—C25—N4	103 (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—C27	179.5 (2)
N2—C9—C10—N1	0.5 (3)	N4—C26—C27—N3	0.0 (3)
C8—N1—C10—C9	0.0 (3)	C25—N3—C27—C26	0.4 (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—C29	40.1 (4)
C9—N2—C11—C12	43.0 (4)	C26—N4—C28—C29	−139.7 (3)
C8—N2—C11—C16	45.7 (3)	C25—N4—C28—C33	−140.4 (3)
C9—N2—C11—C16	−137.7 (3)	C26—N4—C28—C33	39.8 (3)
C16—C11—C12—C13	−0.6 (4)	C33—C28—C29—C30	2.1 (4)
N2—C11—C12—C13	178.7 (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—C15	1.4 (4)	C29—C30—C31—C32	0.3 (4)
C12—C13—C14—C17	−178.9 (3)	C29—C30—C31—C34	−179.2 (3)
C13—C14—C15—C16	0.1 (4)	C30—C31—C32—C33	1.3 (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—C15	2.0 (4)	C29—C28—C33—C32	−0.6 (4)
N2—C11—C16—C15	−177.3 (2)	N4—C28—C33—C32	179.9 (2)

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···F1i	0.95	2.54	3.120 (6)	119
C26—H26···F5ii	0.95	2.40	3.222 (1)	144
C34—H34A···F1iii	0.98	2.53	3.276 (8)	133
C27—H27···Cg3ii	0.95	2.50	3.295 (1)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯F1i	0.95	2.54	3.120 (6)	119
C26—H26⋯F5ii	0.95	2.40	3.222 (1)	144
C34—H34A⋯F1iii	0.98	2.53	3.276 (8)	133
C27—H27⋯Cg3ii	0.95	2.50	3.295 (1)	140

Symmetry codes: (i) ; (ii) ; (iii) .