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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1256–m1257.
Published online 2008 September 13. doi:  10.1107/S1600536808028298
PMCID: PMC2959415

Poly[[{μ3-tris­[2-(4-phenyl-1,2,3-triazol-1-yl)eth­yl]amine}silver(I)] hexa­fluorido­phosphate]

Abstract

The title compound, {[Ag(L)]PF6)n {L is tris­[2-(4-phenyl-1,2,3-triazol-1-yl)eth­yl]amine, C30H30N10}, consists of alternating two-dimensional cationic layers of [Ag(L)]+ and anionic PF6 layers. Each AgI atom is three coordinated in a T-shaped geometry by three N atoms from three ligands. Each ligand links three AgI atoms, generating a two-dimensional network structure with two different metallacycles, A and B. In A, eight coordination units from four ligands connect four AgI atoms, forming a 48-membered ring. In B, four coordination units from two ligands link two AgI atoms, forming a 24-membered ring. Each B ring is surrounded by four A rings, and each A ring has four A and four B rings as neighbours. This cationic layer thus generates a 4.82 topology network, with each AgI centre and ligand acting as a three-connected topological node.

Related literature

For related literature, see: Newkome et al. (1999 [triangle]); Robin & Fromm (2006 [triangle]); Ohi et al. (2004 [triangle], 2005 [triangle]); Obata et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1256-scheme1.jpg

Experimental

Crystal data

  • [Ag(C30H30N10)]PF6
  • M r = 783.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1256-efi1.jpg
  • a = 14.893 (3) Å
  • b = 14.935 (3) Å
  • c = 15.735 (3) Å
  • β = 112.646 (5)°
  • V = 3230.2 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.75 mm−1
  • T = 193.1 K
  • 0.30 × 0.15 × 0.05 mm

Data collection

  • Rigaku Mercury diffractometer
  • Absorption correction: multi-scan (Jacobson, 1998 [triangle]) T min = 0.776, T max = 0.963
  • 31971 measured reflections
  • 7326 independent reflections
  • 4647 reflections with F 2 > 2σ(F 2)
  • R int = 0.075

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.055
  • S = 1.03
  • 7326 reflections
  • 463 parameters
  • All H-atom parameters refined
  • Δρmax = 3.48 e Å−3
  • Δρmin = −2.33 e Å−3

Data collection: CrystalClear (Rigaku/MSC & Rigaku, 2006 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2006 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028298/bt2780sup1.cif

Structure factors: contains datablocks I, I. DOI: 10.1107/S1600536808028298/bt2780Isup2.hkl

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

Acknowledgments

This work was financially supported in part by Grants-in-Aid for Scientific Research (Nos. 19350031 and 19614009) from the Ministry of Education, Culture, Sport, Science and Technology (MEXT) of the Japanese Government, the Japan–German exchange program supported by the Japan Society for the Promotion of Science (JSPS), Nara Women’s University Intramural Grant for Project Research, and grants from Osaka Gas, San-EiGen, and REI Medical Foundation for Chemical Research. The authors thank Professors Yuji Mikata, Takanori Nishioka, Akio Toshimitsu, Isamu Kinoshita and Michael Gottschaldt for valuable contributions.

supplementary crystallographic information

Comment

Coordination polymer complexes have attracted much attention due to their various intriguing framework topologies and their unique properties such as magnetism, physical gas adsorption, ion-exchange, heterogeneous catalysis, and so on (Newkome et al., 1999; Robin et al., 2006). We have recently demonstrated that a C3 symmetric tripodal tripyridine ligand consisting of a 1,3,5-triethylbenzene spacer can be adopted in coordination polymer chemistry to give one- and/or two-dimensional coordination polymer complexes with a variety of network topology (Ohi et al., 2004, 2005). In this study, we synthesized a new C3 symmetric lingad (L) consisting of triethylamine as the spacer and three 1,2,3-triazole groups as the metal binding site by using Huisgen reaction and used this ligand to synthesize a new AgI complex, [[AgI(L)](PF6)]n (I). We report here the crystal structure of AgI complex.

In the title compound (I), the asymmetric unit contained one ligand molecular, one AgI ion, and one PF6- counterion. No solvent molecules were incorporated in the structure. As shown in Fig. 1, each AgI ion features a T-shaped coordination geometry, being coordinated by three nitrogen atoms from three ligands [Ag—N: 2.208 (2)–2.268 (2) Å; N—Ag—N: 113.51 (10)–132.43 (10)°], and each ligand links three AgI atoms to generate a two-dimensional network structure with two different metallacycles A and B. In A, eight coordination moieties from four ligands connected four AgI atoms to form a 48-membered ring. In B, four coordination moieties from two ligands link two AgI atoms to form 24-membered ring. Each B ring is surrounded by four A rings, and each A ring neighbors upon four A and four B rings. Thus, this sheet generates a rare 4.82 topology network with each AgI center and lingad acting as a three-connected topological node (Fig. 2a). The two-dimensional polymer sheets are stacked alternate arranging cationic two-dimensional layers of [AgI(L)]+ and anionic (PF6-) layers to form laminated structure (Fig. 2b), where no specific interaction is probably between the sheets.

Experimental

The ligand tris((4-phenyl-1,2,3-triazole-1-yl)ethyl)amine) (L) was synthesized by using Huisgen reaction, which is known as cycloaddition of azide and acetylene derivatives to give 1,2,3-triazole unit (Obata et al., 2008). The title coordination complex, (I), was synthesized according to the following method. An acetone/CHCl3 (v/v = 1/1, 5 ml) solution of AgIPF6 (50.6 mg, 2.0 x 10 -4 mol) was added slowly to an acetone/CHCl3 (v/v = 1/1, 45 ml) solution of L (104.6 mg, 2.0 x 10 -4 mol). After the mixture was stirred for 1 day under dark, the precipitate was collected by filtration to give white powder. This powder was dissolved in CH3CN and insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give white powder (98.6 mg, yield 64%). Single crystals suitable for X-ray crystallographic analysis were obtained by recrystallization from CH3CN/CHCl3 (v/v = 2/1)/Et2O. Anal. Calcd. for C30H30AgF6N10P: C 45.99, H 3.86, N 17.88. Found: C 46.17, H 4.00, N 17.80.

Refinement

Hydrogen atoms were positioned geometrically (C—H = 0.95 Å) and refined using a riding model with U(H) = 1.2Ueq(C).

Figures

Fig. 1.
The coordination geometry of the AgI atom and the ligated mode of L in the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms omitted for clarity.
Fig. 2.
(a) Two-dimensional 4.82 topology network with 24-membered and 48-membered metallacycles. (b). Three-dimensional packing diagram, showing the alternate arrangement of cationic layers (black) and anionic layers (pink).

Crystal data

[Ag(C30H30N10)]PF6F(000) = 1584.00
Mr = 783.47Dx = 1.611 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 9566 reflections
a = 14.893 (3) Åθ = 4.0–27.5°
b = 14.935 (3) ŵ = 0.75 mm1
c = 15.735 (3) ÅT = 193 K
β = 112.646 (5)°Platelet, colourless
V = 3230.2 (12) Å30.30 × 0.15 × 0.05 mm
Z = 4

Data collection

Rigaku Mercury diffractometer4647 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.075
ω scansθmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)h = −19→16
Tmin = 0.776, Tmax = 0.963k = −19→19
31971 measured reflectionsl = −20→20
7326 independent reflections

Refinement

Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.054All H-atom parameters refined
wR(F2) = 0.055w = 1/[1.0000σ(Fo2)]/(4Fo2)
S = 1.03(Δ/σ)max < 0.001
7326 reflectionsΔρmax = 3.48 e Å3
463 parametersΔρmin = −2.33 e Å3

Special details

Experimental. The ligand tris((4-phenyl-1,2,3-triazole-1-yl)ethyl)amine) (L) was synthesized by using Huisgen reaction, which is known as cycloaddition of azide and acetylene derivatives to give 1,2,3-triazole unit. The conversion of tris(2-chloroethyl)amine (2.21 g, 10.9 mmol) into tris(2-azidoethyl)amine was achieved by addition of 3 mole equivalents of sodium azide to tris(2-chloroethyl)amine in dimethylformamide under stirring at 80 °C. To the THF (100 ml) and water (100 ml) solution of crude tris(2-azidoethyl)amine obtained and phenylacethylene (2.57 g, 25.2 mmol) was added 1 M sodium ascorbate (aq) (0.9 ml) and 7.5 wt% CuSO4 (aq) (2.5 ml) and the mixture was stirred at 50 °C for 1 day. After concentration under reduced pressure, the resulting residue was then suspended in CHCl3, to which an aqueous solution of NH3 was successively added. After washing the organic layer with the NH3 aqueous solution, the organic layer was dried over anhydrous Na2SO4 and concentrated by evaporation. The resulting residue was purified by silica gel column chromatography (eluent; from CHCl3 to ethyl acetate). The organic materials having Rf = 0.21 (eluent; ethyl acetate) were collected (1.73 g, yield 37%). 1H NMR (CDCl3, 400 MHz): δ 3.33 (dt, 6H, J = 4.8, 2.4 Hz, N—CH2CH2–), 4.10 (dt, 6H, J = 4.8, 2.4 Hz, N—CH2CH2–), 6.80 (s, 3H, triazole-H), 7.00 (t, 6H, J = 7.6 Hz Ar-3H, 5H), 7.18 (tt, 3H, J = 7.6, 1.2 Hz, Ar-4H), 7.27 (d, 3H, J = 7.6 Hz, Ar-2H or 6H), 7.28 (d, 3H, J = 7.6 Hz, Ar-2H or 6H). HRMS (FAB, pos): m/z = 531.2729 calcd for [L + H]+, C30H31N10, 531.2733.
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Ag(1)0.45614 (2)0.23636 (2)0.47433 (2)0.02556 (7)
P(1)0.72081 (8)0.21389 (8)0.19893 (9)0.0300 (3)
F(1)0.78327 (16)0.23364 (19)0.13875 (17)0.0552 (8)
F(2)0.65821 (18)0.19439 (16)0.25993 (18)0.0492 (9)
F(3)0.7415 (2)0.31311 (17)0.2382 (2)0.0583 (10)
F(4)0.81644 (17)0.17994 (18)0.28073 (17)0.0477 (8)
F(5)0.70048 (18)0.11394 (16)0.15986 (17)0.0475 (8)
F(6)0.62526 (17)0.2473 (2)0.11681 (17)0.0628 (9)
N(1)0.0406 (2)0.4073 (2)0.3528 (2)0.0209 (9)
N(2)0.2601 (2)0.4507 (2)0.4393 (2)0.0264 (10)
N(3)0.2869 (2)0.3656 (2)0.4548 (2)0.0249 (10)
N(4)0.3631 (2)0.3565 (2)0.4315 (2)0.0223 (9)
N(5)−0.0085 (2)0.5197 (2)0.1746 (2)0.0258 (10)
N(6)−0.0277 (2)0.5971 (2)0.1282 (2)0.0303 (10)
N(7)0.0412 (2)0.6093 (2)0.0966 (2)0.0242 (9)
N(8)0.0859 (2)0.2467 (2)0.26377 (19)0.0231 (9)
N(9)0.0191 (2)0.2593 (2)0.1787 (2)0.0265 (9)
N(10)0.06704 (19)0.2581 (2)0.1214 (2)0.0214 (8)
C(1)0.1011 (2)0.4214 (2)0.4501 (2)0.0245 (11)
C(2)0.1823 (3)0.4872 (2)0.4670 (3)0.0290 (13)
C(3)0.3162 (3)0.4970 (2)0.4061 (2)0.0258 (12)
C(4)0.3837 (2)0.4368 (2)0.4008 (2)0.0196 (10)
C(5)0.4644 (2)0.4490 (2)0.3710 (2)0.0216 (11)
C(6)0.5077 (3)0.3770 (2)0.3441 (3)0.0320 (13)
C(7)0.5821 (3)0.3898 (2)0.3148 (3)0.0355 (13)
C(8)0.6151 (3)0.4762 (2)0.3095 (3)0.0339 (13)
C(9)0.5733 (3)0.5481 (2)0.3355 (3)0.0334 (13)
C(10)0.4994 (2)0.5343 (2)0.3659 (2)0.0262 (12)
C(11)−0.0307 (2)0.4794 (2)0.3191 (2)0.0275 (12)
C(12)−0.0760 (3)0.4862 (2)0.2144 (2)0.0292 (12)
C(13)0.0726 (3)0.4829 (2)0.1727 (2)0.0289 (12)
C(14)0.1058 (2)0.5395 (2)0.1229 (2)0.0213 (11)
C(15)0.1908 (3)0.5339 (2)0.0964 (3)0.0260 (12)
C(16)0.2701 (3)0.4828 (2)0.1481 (3)0.0338 (13)
C(17)0.3512 (3)0.4771 (3)0.1237 (3)0.0435 (15)
C(18)0.3528 (3)0.5245 (3)0.0501 (3)0.0378 (14)
C(19)0.2756 (3)0.5757 (2)−0.0014 (3)0.0373 (14)
C(20)0.1933 (3)0.5808 (2)0.0213 (3)0.0330 (13)
C(21)−0.0095 (2)0.3209 (2)0.3415 (2)0.0264 (12)
C(22)0.0557 (2)0.2428 (2)0.3421 (2)0.0305 (11)
C(23)0.1756 (2)0.2375 (2)0.2625 (2)0.0246 (10)
C(24)0.1642 (2)0.2460 (2)0.1730 (2)0.0186 (9)
C(25)0.2370 (2)0.2422 (2)0.1313 (2)0.0229 (10)
C(26)0.3333 (2)0.2192 (2)0.1856 (2)0.0300 (12)
C(27)0.4044 (2)0.2207 (2)0.1484 (2)0.0348 (13)
C(28)0.3802 (2)0.2411 (3)0.0577 (3)0.0398 (13)
C(29)0.2856 (3)0.2615 (3)0.0021 (2)0.0463 (14)
C(30)0.2140 (2)0.2632 (3)0.0378 (2)0.0371 (12)
H(1)0.06090.44110.48090.031*
H(2)0.13000.36570.47520.031*
H(3)0.20970.50190.53060.035*
H(4)0.15600.53960.43200.035*
H(5)0.31090.55850.38940.030*
H(6)0.48430.31800.34560.038*
H(7)0.61190.34010.29840.043*
H(8)0.66600.48530.28820.042*
H(9)0.59560.60700.33180.039*
H(10)0.47130.58410.38420.032*
H(11)−0.08120.47030.34100.033*
H(12)0.00150.53430.34260.033*
H(13)−0.13020.52560.19730.034*
H(14)−0.09750.42830.19020.035*
H(15)0.10180.42830.20080.034*
H(16)0.26990.45200.20090.042*
H(17)0.40510.44080.15870.051*
H(18)0.40770.52040.03350.046*
H(19)0.27770.6090−0.05210.046*
H(20)0.13900.6162−0.01480.038*
H(21)−0.03440.31360.38830.033*
H(22)−0.06180.32150.28290.033*
H(23)0.02150.18850.33910.038*
H(24)0.11170.24470.39790.038*
H(25)0.23450.22700.31400.029*
H(26)0.34980.20230.24800.033*
H(27)0.47000.20750.18660.041*
H(28)0.42920.24110.03300.049*
H(29)0.26950.2747−0.06120.056*
H(30)0.14880.2782−0.00030.043*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag(1)0.02591 (16)0.01924 (15)0.02906 (17)0.00118 (17)0.00786 (13)−0.00264 (17)
P(1)0.0251 (6)0.0333 (7)0.0370 (7)0.0018 (5)0.0179 (5)−0.0044 (5)
F(1)0.0571 (16)0.0648 (18)0.0679 (18)0.0167 (16)0.0508 (15)0.0146 (17)
F(2)0.0509 (16)0.0533 (17)0.066 (2)−0.0082 (13)0.0474 (15)−0.0081 (14)
F(3)0.059 (2)0.0343 (16)0.100 (2)−0.0089 (14)0.0517 (19)−0.0210 (15)
F(4)0.0291 (15)0.0657 (19)0.0396 (16)−0.0025 (13)0.0036 (13)−0.0018 (13)
F(5)0.0530 (17)0.0392 (16)0.0500 (17)−0.0004 (13)0.0195 (14)−0.0172 (13)
F(6)0.0385 (14)0.073 (2)0.0681 (18)0.0214 (17)0.0110 (13)0.0161 (18)
N(1)0.0190 (18)0.0246 (19)0.0191 (18)0.0041 (14)0.0073 (15)0.0046 (14)
N(2)0.0191 (19)0.027 (2)0.032 (2)0.0078 (15)0.0085 (17)−0.0015 (16)
N(3)0.025 (2)0.0202 (19)0.028 (2)0.0007 (15)0.0092 (17)−0.0004 (15)
N(4)0.0207 (18)0.0194 (18)0.027 (2)−0.0013 (14)0.0091 (16)−0.0030 (15)
N(5)0.027 (2)0.024 (2)0.024 (2)−0.0012 (16)0.0073 (17)0.0025 (16)
N(6)0.033 (2)0.028 (2)0.027 (2)0.0027 (17)0.0082 (18)0.0069 (16)
N(7)0.029 (2)0.0230 (19)0.0200 (19)0.0010 (15)0.0080 (16)0.0034 (15)
N(8)0.0319 (18)0.0146 (19)0.0206 (17)0.0029 (15)0.0076 (15)0.0042 (15)
N(9)0.0206 (16)0.0262 (19)0.0275 (18)−0.0016 (16)0.0035 (14)0.0025 (17)
N(10)0.0153 (15)0.0141 (17)0.0324 (18)−0.0031 (14)0.0065 (14)−0.0005 (15)
C(1)0.023 (2)0.036 (2)0.019 (2)0.0077 (19)0.0132 (19)0.0000 (19)
C(2)0.026 (2)0.037 (2)0.026 (2)0.009 (2)0.012 (2)−0.002 (2)
C(3)0.029 (2)0.021 (2)0.025 (2)−0.0017 (18)0.008 (2)0.0042 (18)
C(4)0.020 (2)0.016 (2)0.019 (2)0.0022 (16)0.0027 (18)0.0006 (16)
C(5)0.022 (2)0.017 (2)0.024 (2)0.0005 (17)0.0068 (19)−0.0013 (17)
C(6)0.033 (2)0.023 (2)0.039 (2)−0.0044 (19)0.012 (2)−0.004 (2)
C(7)0.028 (2)0.034 (2)0.045 (3)0.003 (2)0.015 (2)−0.006 (2)
C(8)0.024 (2)0.041 (2)0.040 (2)−0.004 (2)0.016 (2)0.001 (2)
C(9)0.028 (2)0.026 (2)0.044 (2)−0.007 (2)0.011 (2)−0.002 (2)
C(10)0.026 (2)0.022 (2)0.033 (2)0.0018 (18)0.013 (2)0.0001 (19)
C(11)0.023 (2)0.030 (2)0.029 (2)0.0057 (19)0.0093 (19)0.0033 (19)
C(12)0.026 (2)0.034 (2)0.026 (2)0.0013 (19)0.009 (2)0.003 (2)
C(13)0.034 (2)0.020 (2)0.031 (2)0.0055 (19)0.010 (2)0.0060 (19)
C(14)0.028 (2)0.016 (2)0.016 (2)−0.0004 (18)0.0034 (19)−0.0009 (16)
C(15)0.030 (2)0.020 (2)0.025 (2)−0.0051 (19)0.006 (2)−0.0044 (18)
C(16)0.037 (2)0.032 (2)0.035 (2)−0.002 (2)0.018 (2)0.007 (2)
C(17)0.037 (2)0.048 (3)0.042 (3)0.010 (2)0.012 (2)0.009 (2)
C(18)0.029 (2)0.046 (3)0.040 (2)0.002 (2)0.014 (2)−0.000 (2)
C(19)0.049 (3)0.031 (2)0.036 (2)−0.006 (2)0.020 (2)0.003 (2)
C(20)0.040 (2)0.026 (2)0.029 (2)0.000 (2)0.009 (2)0.006 (2)
C(21)0.025 (2)0.031 (2)0.026 (2)0.0000 (19)0.0136 (19)0.0095 (19)
C(22)0.041 (2)0.027 (2)0.028 (2)−0.001 (2)0.018 (2)0.004 (2)
C(23)0.020 (2)0.029 (2)0.024 (2)0.004 (2)0.0074 (17)0.003 (2)
C(24)0.0205 (19)0.009 (2)0.0212 (19)−0.0041 (16)0.0022 (16)−0.0047 (16)
C(25)0.0212 (19)0.021 (2)0.023 (2)−0.0004 (18)0.0052 (16)−0.0066 (19)
C(26)0.026 (2)0.026 (2)0.030 (2)0.0029 (19)0.003 (2)0.0026 (19)
C(27)0.020 (2)0.041 (2)0.040 (2)0.005 (2)0.008 (2)−0.005 (2)
C(28)0.030 (2)0.051 (3)0.042 (2)−0.004 (2)0.019 (2)−0.011 (2)
C(29)0.039 (2)0.072 (3)0.029 (2)−0.006 (2)0.014 (2)0.002 (2)
C(30)0.025 (2)0.058 (2)0.024 (2)−0.005 (2)0.0050 (18)0.003 (2)

Geometric parameters (Å, °)

Ag(1)—N(4)2.208 (2)C(17)—C(18)1.365 (7)
Ag(1)—N(7)i2.210 (3)C(18)—C(19)1.359 (5)
Ag(1)—N(10)ii2.268 (2)C(19)—C(20)1.405 (8)
P(1)—F(1)1.590 (3)C(21)—C(22)1.516 (5)
P(1)—F(2)1.601 (3)C(23)—C(24)1.359 (5)
P(1)—F(3)1.590 (2)C(24)—C(25)1.468 (6)
P(1)—F(4)1.591 (2)C(25)—C(26)1.401 (4)
P(1)—F(5)1.598 (2)C(25)—C(30)1.410 (5)
P(1)—F(6)1.590 (2)C(26)—C(27)1.395 (7)
N(1)—C(1)1.462 (4)C(27)—C(28)1.365 (6)
N(1)—C(11)1.462 (4)C(28)—C(29)1.376 (5)
N(1)—C(21)1.466 (4)C(29)—C(30)1.385 (7)
N(2)—N(3)1.327 (4)C(1)—H(1)0.950
N(2)—C(2)1.489 (6)C(1)—H(2)0.950
N(2)—C(3)1.336 (6)C(2)—H(3)0.950
N(3)—N(4)1.327 (5)C(2)—H(4)0.950
N(4)—C(4)1.372 (5)C(3)—H(5)0.950
N(5)—N(6)1.338 (4)C(6)—H(6)0.950
N(5)—C(12)1.463 (6)C(7)—H(7)0.950
N(5)—C(13)1.337 (6)C(8)—H(8)0.950
N(6)—N(7)1.314 (6)C(9)—H(9)0.950
N(7)—C(14)1.370 (4)C(10)—H(10)0.950
N(8)—N(9)1.339 (3)C(11)—H(11)0.950
N(8)—C(22)1.466 (5)C(11)—H(12)0.950
N(8)—C(23)1.350 (5)C(12)—H(13)0.950
N(9)—N(10)1.349 (5)C(12)—H(14)0.950
N(10)—C(24)1.372 (3)C(13)—H(15)0.950
C(1)—C(2)1.501 (5)C(16)—H(16)0.950
C(3)—C(4)1.375 (6)C(17)—H(17)0.950
C(4)—C(5)1.460 (6)C(18)—H(18)0.950
C(5)—C(6)1.402 (6)C(19)—H(19)0.950
C(5)—C(10)1.390 (5)C(20)—H(20)0.950
C(6)—C(7)1.368 (7)C(21)—H(21)0.950
C(7)—C(8)1.394 (6)C(21)—H(22)0.950
C(8)—C(9)1.381 (6)C(22)—H(23)0.950
C(9)—C(10)1.374 (7)C(22)—H(24)0.950
C(11)—C(12)1.524 (5)C(23)—H(25)0.950
C(13)—C(14)1.368 (6)C(26)—H(26)0.950
C(14)—C(15)1.479 (7)C(27)—H(27)0.950
C(15)—C(16)1.379 (5)C(28)—H(28)0.950
C(15)—C(20)1.386 (6)C(29)—H(29)0.950
C(16)—C(17)1.404 (8)C(30)—H(30)0.950
F(1)···N(3)iii3.271 (4)N(10)···H(20)ix3.433
F(1)···N(9)iv3.343 (3)C(4)···H(10)vii3.253
F(1)···C(9)v3.427 (5)C(7)···H(3)vii3.513
F(1)···C(19)vi3.477 (5)C(8)···H(3)vii2.863
F(2)···N(6)i3.409 (5)C(9)···H(3)vii3.195
F(2)···C(7)3.362 (5)C(11)···H(1)xiii3.550
F(2)···C(12)i3.421 (5)C(12)···H(19)ix3.414
F(2)···C(27)3.523 (4)C(12)···H(20)ix3.289
F(3)···C(7)3.256 (6)C(13)···H(20)ix3.502
F(3)···C(8)3.516 (5)C(19)···H(13)ix3.368
F(3)···C(21)iv3.430 (4)C(19)···H(14)ix3.131
F(4)···C(9)v3.498 (5)C(20)···H(13)ix3.572
F(4)···C(21)iv3.188 (4)C(20)···H(14)ix3.079
F(4)···C(22)iv3.445 (4)C(21)···H(28)viii3.591
F(5)···C(1)iii3.099 (4)C(28)···H(21)iii3.465
F(5)···C(2)iii3.307 (5)H(1)···F(5)viii2.901
F(5)···C(8)v3.316 (5)H(1)···F(6)viii3.440
F(5)···C(9)v3.484 (5)H(1)···C(11)xiii3.550
F(5)···C(11)i3.345 (5)H(1)···H(1)xiii2.754
F(6)···C(1)iii3.554 (4)H(1)···H(11)xiii3.006
F(6)···C(27)3.533 (5)H(1)···H(12)xiii3.271
F(6)···C(28)3.403 (4)H(2)···P(1)viii3.460
N(2)···C(9)vii3.456 (4)H(2)···F(1)viii3.084
N(3)···F(1)viii3.271 (4)H(2)···F(5)viii2.700
N(3)···C(9)vii3.405 (4)H(2)···F(6)viii2.818
N(4)···C(10)vii3.463 (4)H(3)···F(5)viii2.714
N(5)···C(20)ix3.578 (4)H(3)···C(7)vii3.513
N(6)···F(2)x3.409 (5)H(3)···C(8)vii2.863
N(9)···F(1)xi3.343 (3)H(3)···C(9)vii3.195
C(1)···F(5)viii3.099 (4)H(3)···H(8)vii2.744
C(1)···F(6)viii3.554 (4)H(3)···H(9)vii3.303
C(2)···F(5)viii3.307 (5)H(3)···H(11)xiii3.300
C(4)···C(10)vii3.431 (5)H(7)···P(1)3.254
C(7)···F(2)3.362 (5)H(7)···F(2)2.429
C(7)···F(3)3.256 (6)H(7)···F(3)2.489
C(8)···F(3)3.516 (5)H(7)···F(6)3.251
C(8)···F(5)xii3.316 (5)H(8)···F(3)3.030
C(9)···F(1)xii3.427 (5)H(8)···F(4)xii3.148
C(9)···F(4)xii3.498 (5)H(8)···F(5)xii2.657
C(9)···F(5)xii3.484 (5)H(8)···H(3)vii2.744
C(9)···N(2)vii3.456 (4)H(8)···H(11)iv3.536
C(9)···N(3)vii3.405 (4)H(9)···P(1)xii3.358
C(10)···N(4)vii3.463 (4)H(9)···F(1)xii2.530
C(10)···C(4)vii3.431 (5)H(9)···F(4)xii2.797
C(11)···F(5)x3.345 (5)H(9)···F(5)xii2.990
C(12)···F(2)x3.421 (5)H(9)···N(2)vii3.517
C(12)···C(20)ix3.582 (5)H(9)···N(3)vii3.159
C(19)···F(1)vi3.477 (5)H(9)···N(4)vii3.576
C(20)···N(5)ix3.578 (4)H(9)···H(3)vii3.303
C(20)···C(12)ix3.582 (5)H(10)···Ag(1)vii3.386
C(21)···F(3)xi3.430 (4)H(10)···N(3)vii3.595
C(21)···F(4)xi3.188 (4)H(10)···N(4)vii3.127
C(22)···F(4)xi3.445 (4)H(10)···C(4)vii3.253
C(27)···F(2)3.523 (4)H(11)···F(3)xi3.437
C(27)···F(6)3.533 (5)H(11)···F(5)x2.782
C(28)···F(6)3.403 (4)H(11)···H(1)xiii3.006
Ag(1)···H(10)vii3.386H(11)···H(3)xiii3.300
P(1)···H(2)iii3.460H(11)···H(8)xi3.536
P(1)···H(7)3.254H(12)···F(2)x3.320
P(1)···H(9)v3.358H(12)···F(5)x3.221
P(1)···H(19)vi3.519H(12)···H(1)xiii3.271
P(1)···H(22)iv3.394H(13)···F(2)x2.682
P(1)···H(29)ii3.564H(13)···F(5)x3.114
F(1)···H(2)iii3.084H(13)···C(19)ix3.368
F(1)···H(9)v2.530H(13)···C(20)ix3.572
F(1)···H(14)iv3.340H(13)···H(19)ix3.198
F(1)···H(19)vi2.694H(13)···H(20)ix3.530
F(1)···H(20)vi3.451H(14)···F(1)xi3.340
F(1)···H(22)iv2.857H(14)···F(3)xi3.267
F(2)···H(7)2.429H(14)···C(19)ix3.131
F(2)···H(12)i3.320H(14)···C(20)ix3.079
F(2)···H(13)i2.682H(14)···H(19)ix2.783
F(2)···H(27)2.595H(14)···H(20)ix2.670
F(2)···H(29)ii2.700H(18)···H(18)vi3.360
F(3)···H(7)2.489H(19)···P(1)vi3.519
F(3)···H(8)3.030H(19)···F(1)vi2.694
F(3)···H(11)iv3.437H(19)···F(3)vi3.062
F(3)···H(14)iv3.267H(19)···F(6)vi2.978
F(3)···H(19)vi3.062H(19)···C(12)ix3.414
F(3)···H(21)iv3.263H(19)···H(13)ix3.198
F(3)···H(22)iv2.740H(19)···H(14)ix2.783
F(3)···H(29)ii3.293H(20)···F(1)vi3.451
F(4)···H(8)v3.148H(20)···N(5)ix3.234
F(4)···H(9)v2.797H(20)···N(9)ix3.312
F(4)···H(21)iv2.981H(20)···N(10)ix3.433
F(4)···H(22)iv2.777H(20)···C(12)ix3.289
F(4)···H(23)iv2.833H(20)···C(13)ix3.502
F(4)···H(29)ii2.912H(20)···H(13)ix3.530
F(5)···H(1)iii2.901H(20)···H(14)ix2.670
F(5)···H(2)iii2.700H(21)···F(3)xi3.263
F(5)···H(3)iii2.714H(21)···F(4)xi2.981
F(5)···H(8)v2.657H(21)···F(6)viii3.582
F(5)···H(9)v2.990H(21)···C(28)viii3.465
F(5)···H(11)i2.782H(21)···H(28)viii2.664
F(5)···H(12)i3.221H(21)···H(29)viii3.563
F(5)···H(13)i3.114H(22)···P(1)xi3.394
F(6)···H(1)iii3.440H(22)···F(1)xi2.857
F(6)···H(2)iii2.818H(22)···F(3)xi2.740
F(6)···H(7)3.251H(22)···F(4)xi2.777
F(6)···H(19)vi2.978H(23)···F(4)xi2.833
F(6)···H(21)iii3.582H(24)···F(6)viii3.374
F(6)···H(24)iii3.374H(27)···F(2)2.595
F(6)···H(27)2.977H(27)···F(6)2.977
F(6)···H(28)2.703H(28)···F(6)2.703
N(2)···H(9)vii3.517H(28)···C(21)iii3.591
N(3)···H(9)vii3.159H(28)···H(21)iii2.664
N(3)···H(10)vii3.595H(29)···P(1)xiv3.564
N(4)···H(9)vii3.576H(29)···F(2)xiv2.700
N(4)···H(10)vii3.127H(29)···F(3)xiv3.293
N(5)···H(20)ix3.234H(29)···F(4)xiv2.912
N(6)···H(30)ix2.825H(29)···H(21)iii3.563
N(7)···H(30)ix3.136H(30)···N(6)ix2.825
N(9)···H(20)ix3.312H(30)···N(7)ix3.136
N(4)—Ag(1)—N(7)i132.43 (10)C(23)—C(24)—C(25)129.9 (2)
N(4)—Ag(1)—N(10)ii114.02 (10)C(24)—C(25)—C(26)119.7 (3)
N(7)i—Ag(1)—N(10)ii113.51 (10)C(24)—C(25)—C(30)122.2 (3)
F(1)—P(1)—F(2)179.70 (15)C(26)—C(25)—C(30)118.1 (4)
F(1)—P(1)—F(3)89.34 (18)C(25)—C(26)—C(27)120.3 (3)
F(1)—P(1)—F(4)89.67 (14)C(26)—C(27)—C(28)120.3 (3)
F(1)—P(1)—F(5)90.68 (16)C(27)—C(28)—C(29)120.6 (4)
F(1)—P(1)—F(6)90.20 (15)C(28)—C(29)—C(30)120.4 (4)
F(2)—P(1)—F(3)90.39 (17)C(25)—C(30)—C(29)120.2 (3)
F(2)—P(1)—F(4)90.20 (15)N(1)—C(1)—H(1)108.9
F(2)—P(1)—F(5)89.59 (15)N(1)—C(1)—H(2)107.9
F(2)—P(1)—F(6)89.93 (14)C(2)—C(1)—H(1)109.2
F(3)—P(1)—F(4)90.18 (14)C(2)—C(1)—H(2)107.1
F(3)—P(1)—F(5)179.69 (15)H(1)—C(1)—H(2)109.5
F(3)—P(1)—F(6)90.13 (15)N(2)—C(2)—H(3)109.0
F(4)—P(1)—F(5)89.51 (13)N(2)—C(2)—H(4)109.0
F(4)—P(1)—F(6)179.66 (16)C(1)—C(2)—H(3)109.2
F(5)—P(1)—F(6)90.17 (14)C(1)—C(2)—H(4)108.3
C(1)—N(1)—C(11)110.0 (3)H(3)—C(2)—H(4)109.5
C(1)—N(1)—C(21)109.5 (3)N(2)—C(3)—H(5)127.7
C(11)—N(1)—C(21)109.9 (2)C(4)—C(3)—H(5)126.8
N(3)—N(2)—C(2)120.7 (3)C(5)—C(6)—H(6)119.2
N(3)—N(2)—C(3)112.2 (3)C(7)—C(6)—H(6)119.4
C(2)—N(2)—C(3)126.8 (3)C(6)—C(7)—H(7)120.3
N(2)—N(3)—N(4)106.0 (3)C(8)—C(7)—H(7)119.7
Ag(1)—N(4)—N(3)120.1 (2)C(7)—C(8)—H(8)120.1
Ag(1)—N(4)—C(4)128.3 (2)C(9)—C(8)—H(8)120.4
N(3)—N(4)—C(4)109.8 (3)C(8)—C(9)—H(9)119.5
N(6)—N(5)—C(12)119.4 (3)C(10)—C(9)—H(9)120.5
N(6)—N(5)—C(13)110.4 (3)C(5)—C(10)—H(10)118.8
C(12)—N(5)—C(13)130.1 (3)C(9)—C(10)—H(10)119.5
N(5)—N(6)—N(7)106.9 (3)N(1)—C(11)—H(11)109.2
Ag(1)x—N(7)—N(6)118.6 (2)N(1)—C(11)—H(12)107.9
Ag(1)x—N(7)—C(14)131.2 (3)C(12)—C(11)—H(11)108.6
N(6)—N(7)—C(14)110.0 (3)C(12)—C(11)—H(12)108.0
N(9)—N(8)—C(22)119.7 (3)H(11)—C(11)—H(12)109.5
N(9)—N(8)—C(23)111.0 (3)N(5)—C(12)—H(13)108.4
C(22)—N(8)—C(23)129.3 (2)N(5)—C(12)—H(14)108.7
N(8)—N(9)—N(10)106.6 (2)C(11)—C(12)—H(13)108.8
Ag(1)xiv—N(10)—N(9)108.43 (17)C(11)—C(12)—H(14)108.2
Ag(1)xiv—N(10)—C(24)142.8 (2)H(13)—C(12)—H(14)109.5
N(9)—N(10)—C(24)108.4 (2)N(5)—C(13)—H(15)126.8
N(1)—C(1)—C(2)114.2 (3)C(14)—C(13)—H(15)126.5
N(2)—C(2)—C(1)111.9 (3)C(15)—C(16)—H(16)119.6
N(2)—C(3)—C(4)105.5 (3)C(17)—C(16)—H(16)120.2
N(4)—C(4)—C(3)106.4 (4)C(16)—C(17)—H(17)120.0
N(4)—C(4)—C(5)123.0 (3)C(18)—C(17)—H(17)120.1
C(3)—C(4)—C(5)130.5 (3)C(17)—C(18)—H(18)119.8
C(4)—C(5)—C(6)122.2 (3)C(19)—C(18)—H(18)119.5
C(4)—C(5)—C(10)120.4 (3)C(18)—C(19)—H(19)120.1
C(6)—C(5)—C(10)117.3 (4)C(20)—C(19)—H(19)119.9
C(5)—C(6)—C(7)121.4 (4)C(15)—C(20)—H(20)119.7
C(6)—C(7)—C(8)120.0 (4)C(19)—C(20)—H(20)120.2
C(7)—C(8)—C(9)119.5 (4)N(1)—C(21)—H(21)109.8
C(8)—C(9)—C(10)120.0 (4)N(1)—C(21)—H(22)107.4
C(5)—C(10)—C(9)121.7 (4)C(22)—C(21)—H(21)110.3
N(1)—C(11)—C(12)113.5 (3)C(22)—C(21)—H(22)107.3
N(5)—C(12)—C(11)113.2 (3)H(21)—C(21)—H(22)109.5
N(5)—C(13)—C(14)106.7 (3)N(8)—C(22)—H(23)109.0
N(7)—C(14)—C(13)106.0 (4)N(8)—C(22)—H(24)109.4
N(7)—C(14)—C(15)122.4 (3)C(21)—C(22)—H(23)109.0
C(13)—C(14)—C(15)131.6 (3)C(21)—C(22)—H(24)108.3
C(14)—C(15)—C(16)119.7 (4)H(23)—C(22)—H(24)109.5
C(14)—C(15)—C(20)121.2 (3)N(8)—C(23)—H(25)126.8
C(16)—C(15)—C(20)119.0 (4)C(24)—C(23)—H(25)127.2
C(15)—C(16)—C(17)120.2 (4)C(25)—C(26)—H(26)119.6
C(16)—C(17)—C(18)119.9 (4)C(27)—C(26)—H(26)120.1
C(17)—C(18)—C(19)120.7 (5)C(26)—C(27)—H(27)119.6
C(18)—C(19)—C(20)120.0 (4)C(28)—C(27)—H(27)120.1
C(15)—C(20)—C(19)120.1 (3)C(27)—C(28)—H(28)119.5
N(1)—C(21)—C(22)112.4 (3)C(29)—C(28)—H(28)120.0
N(8)—C(22)—C(21)111.5 (3)C(28)—C(29)—H(29)119.8
N(8)—C(23)—C(24)106.1 (2)C(30)—C(29)—H(29)119.8
N(10)—C(24)—C(23)107.9 (3)C(25)—C(30)—H(30)119.3
N(10)—C(24)—C(25)122.2 (3)C(29)—C(30)—H(30)120.5
N(4)—Ag(1)—N(7)i—N(6)i104.7 (2)Ag(1)xiv—N(10)—C(24)—C(23)−170.2 (3)
N(4)—Ag(1)—N(7)i—C(14)i−68.5 (3)Ag(1)xiv—N(10)—C(24)—C(25)8.7 (5)
N(7)i—Ag(1)—N(4)—N(3)96.6 (2)N(9)—N(10)—C(24)—C(23)1.4 (3)
N(7)i—Ag(1)—N(4)—C(4)−100.5 (3)N(9)—N(10)—C(24)—C(25)−179.6 (3)
N(4)—Ag(1)—N(10)ii—N(9)ii66.5 (2)N(1)—C(1)—C(2)—N(2)−70.9 (4)
N(4)—Ag(1)—N(10)ii—C(24)ii−105.2 (3)N(2)—C(3)—C(4)—N(4)0.2 (3)
N(10)ii—Ag(1)—N(4)—N(3)−80.8 (2)N(2)—C(3)—C(4)—C(5)−178.9 (3)
N(10)ii—Ag(1)—N(4)—C(4)82.1 (3)N(4)—C(4)—C(5)—C(6)20.4 (5)
N(7)i—Ag(1)—N(10)ii—N(9)ii−111.4 (2)N(4)—C(4)—C(5)—C(10)−161.5 (3)
N(7)i—Ag(1)—N(10)ii—C(24)ii76.9 (4)C(3)—C(4)—C(5)—C(6)−160.5 (3)
N(10)ii—Ag(1)—N(7)i—N(6)i−77.9 (2)C(3)—C(4)—C(5)—C(10)17.6 (5)
N(10)ii—Ag(1)—N(7)i—C(14)i108.9 (3)C(4)—C(5)—C(6)—C(7)178.8 (3)
C(1)—N(1)—C(11)—C(12)162.9 (3)C(4)—C(5)—C(10)—C(9)−178.0 (3)
C(11)—N(1)—C(1)—C(2)−80.9 (4)C(6)—C(5)—C(10)—C(9)0.2 (4)
C(1)—N(1)—C(21)—C(22)−79.6 (4)C(10)—C(5)—C(6)—C(7)0.6 (5)
C(21)—N(1)—C(1)—C(2)158.2 (3)C(5)—C(6)—C(7)—C(8)−1.3 (5)
C(11)—N(1)—C(21)—C(22)159.5 (3)C(6)—C(7)—C(8)—C(9)1.1 (5)
C(21)—N(1)—C(11)—C(12)−76.5 (4)C(7)—C(8)—C(9)—C(10)−0.3 (5)
N(3)—N(2)—C(2)—C(1)−39.0 (4)C(8)—C(9)—C(10)—C(5)−0.3 (5)
C(2)—N(2)—N(3)—N(4)−173.8 (2)N(1)—C(11)—C(12)—N(5)−71.1 (4)
N(3)—N(2)—C(3)—C(4)−0.4 (4)N(5)—C(13)—C(14)—N(7)−0.0 (3)
C(3)—N(2)—N(3)—N(4)0.4 (3)N(5)—C(13)—C(14)—C(15)−179.0 (3)
C(2)—N(2)—C(3)—C(4)173.3 (3)N(7)—C(14)—C(15)—C(16)157.3 (3)
C(3)—N(2)—C(2)—C(1)147.8 (3)N(7)—C(14)—C(15)—C(20)−21.3 (5)
N(2)—N(3)—N(4)—Ag(1)165.6 (2)C(13)—C(14)—C(15)—C(16)−23.9 (6)
N(2)—N(3)—N(4)—C(4)−0.2 (3)C(13)—C(14)—C(15)—C(20)157.5 (4)
Ag(1)—N(4)—C(4)—C(3)−164.4 (2)C(14)—C(15)—C(16)—C(17)−180.0 (3)
Ag(1)—N(4)—C(4)—C(5)14.9 (4)C(14)—C(15)—C(20)—C(19)178.9 (3)
N(3)—N(4)—C(4)—C(3)−0.0 (3)C(16)—C(15)—C(20)—C(19)0.2 (5)
N(3)—N(4)—C(4)—C(5)179.2 (3)C(20)—C(15)—C(16)—C(17)−1.3 (6)
N(6)—N(5)—C(12)—C(11)−117.3 (3)C(15)—C(16)—C(17)—C(18)2.1 (6)
C(12)—N(5)—N(6)—N(7)−177.2 (2)C(16)—C(17)—C(18)—C(19)−1.7 (6)
N(6)—N(5)—C(13)—C(14)−0.1 (3)C(17)—C(18)—C(19)—C(20)0.6 (6)
C(13)—N(5)—N(6)—N(7)0.1 (3)C(18)—C(19)—C(20)—C(15)0.2 (5)
C(12)—N(5)—C(13)—C(14)176.9 (3)N(1)—C(21)—C(22)—N(8)−63.9 (3)
C(13)—N(5)—C(12)—C(11)66.0 (5)N(8)—C(23)—C(24)—N(10)−1.4 (4)
N(5)—N(6)—N(7)—Ag(1)x−174.7 (2)N(8)—C(23)—C(24)—C(25)179.7 (3)
N(5)—N(6)—N(7)—C(14)−0.1 (3)N(10)—C(24)—C(25)—C(26)−172.5 (3)
Ag(1)x—N(7)—C(14)—C(13)173.7 (2)N(10)—C(24)—C(25)—C(30)9.1 (5)
Ag(1)x—N(7)—C(14)—C(15)−7.2 (5)C(23)—C(24)—C(25)—C(26)6.2 (6)
N(6)—N(7)—C(14)—C(13)0.1 (3)C(23)—C(24)—C(25)—C(30)−172.2 (4)
N(6)—N(7)—C(14)—C(15)179.2 (3)C(24)—C(25)—C(26)—C(27)−176.0 (3)
N(9)—N(8)—C(22)—C(21)−49.6 (4)C(24)—C(25)—C(30)—C(29)177.9 (4)
C(22)—N(8)—N(9)—N(10)−178.8 (2)C(26)—C(25)—C(30)—C(29)−0.5 (6)
N(9)—N(8)—C(23)—C(24)0.9 (4)C(30)—C(25)—C(26)—C(27)2.4 (5)
C(23)—N(8)—N(9)—N(10)−0.0 (3)C(25)—C(26)—C(27)—C(28)−2.5 (6)
C(22)—N(8)—C(23)—C(24)179.5 (3)C(26)—C(27)—C(28)—C(29)0.7 (6)
C(23)—N(8)—C(22)—C(21)131.9 (3)C(27)—C(28)—C(29)—C(30)1.3 (7)
N(8)—N(9)—N(10)—Ag(1)xiv173.8 (2)C(28)—C(29)—C(30)—C(25)−1.3 (7)
N(8)—N(9)—N(10)—C(24)−0.9 (3)

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) x+1, y, z; (v) −x+3/2, y−1/2, −z+1/2; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+1, −z+1; (viii) x−1/2, −y+1/2, z+1/2; (ix) −x, −y+1, −z; (x) −x+1/2, y+1/2, −z+1/2; (xi) x−1, y, z; (xii) −x+3/2, y+1/2, −z+1/2; (xiii) −x, −y+1, −z+1; (xiv) x−1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2780).

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