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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1618–m1619.
Published online 2008 November 26. doi:  10.1107/S1600536808038907
PMCID: PMC2959965

catena-Poly[[[N′-(4-cyano­benzyl­idene)nicotinohydrazide)silver(I)]-μ-N′-(4-cyano­benzyl­idene)nicotinohydrazide] hexa­fluorido­phosphate]

Abstract

In the title polymer, {[Ag(C14H10N4O)2]PF6}n, each AgI ion is coordinated by two N atoms from two pyridyl rings of independent N′-(4-cyano­benzyl­idene)nicotinohydrazide ligands, and one N atom from one carbonitrile group of a symmetry-related ligand in a distorted T-shaped geometry. The ligands exhibit two modes of coordination. One acts as a bridge connecting Ag atoms to form one-dimensional chains along [An external file that holds a picture, illustration, etc.
Object name is e-64-m1618-efi4.jpg01]. The other acts as a terminal monodentate ligand, coordinating to Ag through its pyridyl N atom. Two neighbouring anti­parallel chains in the crystal are connected through N—H(...)O hydrogen bonds. Other adjacent chains are packed via Ag(...)O inter­actions, with Ag(...)O separations of 2.876 (2) Å. In addition, PF6 counter-anions inter­act with the hydrazone groups through N—H(...)F hydrogen bonds. The PF6 anion is disordered over two sites, with occupancies of 0.773 (8) and 0.227 (8).

Related literature

For background on fluorescent silver coordination complexes, see: Dong et al. (2004 [triangle]); Sumby & Hardie (2005 [triangle]). For related structures, see: Niu et al. (2007 [triangle], 2008 [triangle]); Vatsadze et al. (2004 [triangle]); Zheng et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1618-scheme1.jpg

Experimental

Crystal data

  • [Ag(C14H10N4O)2]PF6
  • M r = 753.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1618-efi5.jpg
  • a = 22.3252 (17) Å
  • b = 13.6939 (11) Å
  • c = 19.8523 (16) Å
  • β = 99.9770 (10)°
  • V = 5977.4 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.81 mm−1
  • T = 173 (2) K
  • 0.44 × 0.32 × 0.29 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Siemens, 1996 [triangle]) T min = 0.718, T max = 0.799
  • 19020 measured reflections
  • 6823 independent reflections
  • 5105 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.099
  • S = 1.03
  • 6823 reflections
  • 460 parameters
  • 96 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.92 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 2005 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038907/bh2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038907/bh2203Isup2.hkl

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

Acknowledgments

We are grateful to Mrs Li (Wuhan University) for her assistance with the X-ray crystallographic analysis. We also gratefully acknowledge financial support from the Natural Science Foundation of Henan Province (2008B150008) and the Science and Technology Key Task of Henan Province (0624040011).

supplementary crystallographic information

Comment

Pyridyl organic ligands with carbonitrile groups can be used to construct silver coordination complexes with fascinating structures and good fluorescent properties (Sumby & Hardie, 2005; Dong et al., 2004). We also synthesized one-dimensional and two-dimensional silver coordination polymers using this kind of ligands (Niu et al., 2007, 2008). Herein, a one-dimensional silver coordination polymer constructed with a new bridging ligand of this type, 4-cyanobenzylidene nicotinohydrazide, is reported.

In the title compound, (I), the central AgI ion is coordinated by two N atoms from two pyridyl rings of two different ligands (N1, N2) and one N atom from one carbonitrile group of another ligand [N8i, symmetry code: (i) x - 1/2, -y + 3/2, z + 1/2], forming a slightly distorted T-shaped coordination environment (Fig. 1). The N1—Ag1—N2 bond angle is 156.22 (8)°, indicating these three atoms are not exactly in one line. Bond angles N1—Ag1—N8i and N2—Ag1—N8i are larger than 90° (Table 1). The Ag—N bond distances for pyridyl rings are in the range 2.172 (2)–2.199 (2) Å, which is smaller than N—Ag bond distance for the carbonitrile group (Table 1).

One 4-cyanobenzylidene nicotinohydrazide molecule acts as a µ2-bridging ligand, by coordinating pyridyl and carbonitrile N atoms. Each bridging ligand connects two silver atoms together by one pyridyl N atom (N1) and one carbonitrile N atom (N8) to form a one-dimensional chain along the [-1 0 1] direction. The separation between two neighbouring Ag atoms in one chain is about 16 Å. Meanwhile, the other independent ligand is acting as a terminal ligand, being coordinated to Ag only through a pyridyl N atom. Two terminal ligands connected to two adjacent Ag atoms in one chain are located at the opposite positions away from the chain (Fig. 2).

There are hydrogen bonds between uncoordinating groups, including pyridyl rings of terminal ligands and all hydrazone groups, as well as other groups like counteranions. On one hand, counteranions PF6- interact with the ligands in the polymer through N—H···F hydrogen bonds (Table 2). Four F atoms (F1 to F4) of the PF6- anion are disordered over two sites, with occupancies 0.773 (8) and 0.227 (8). On the other hand, there are also N—H···O hydrogen bonds between two neighbouring antiparallel chains in the crystal (Fig. 3). In addition to these intermolecular contacts, there are weak Ag···O interactions between one O atom (O1) of the terminal ligand and one Ag atom in the neighbouring chain, with Ag···O separations of 2.876 (2) Å. These noncovalent interactions have large contributions to the supramolecular three-dimensional framework.

One-dimensional AgI coordination polymers with T-shaped coordination geometry were previously described in a few compounds: {[Ag(2,6-di(3-pyridylmethylidene) cyclohexanone)](NO3)}n (Vatsadze et al., 2004) and {[Ag(2,2'-(methylenebis(thio)) bis(pyrimidine))](NO3)}n (Zheng et al., 2003). The N—Ag—N bond angles in these two compounds deviate from 180° (ca. 158 and 131°, respectively), which are close to that observed in (I).

Experimental

A solution of AgPF6 (0.025 g, 0.1 mmol) in CH3OH (10 ml) was carefully layered on a CH3OH/CHCl3 solution (5 ml/10 ml) of 4-cyanobenzylidene nicotinohydrazide (0.025 g, 0.1 mmol) in a straight glass tube. About ten days later, colourless single crystals suitable for X-ray analysis were obtained (yield: ca. 50%). Analysis, calculated for C28H20AgN8O2F6P: C 44.64, H 2.68, N 14.87%; found: C 44.79, H 2.69, N 14.99%.

Refinement

C-bound H atoms were placed in calculated positions and refined using a riding model [C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C)]. The N-bound H atoms were first introduced in calculated positions, and then their positions and displacement parameters were refined with the N—H bond lengths restrained to 0.88 (2) Å. Four F atoms (F1/F2/F3/F4) of the hexafluorophosphate anion are disordered over two positions (F1'/F2'/F3'/F4'), and all P—F bond lengths were restrained to a target value of 1.58 (2) Å. Displacement parameters for disordered F atoms were also subjected to restraints. The final difference map had a highest peak at 0.88 Å from Ag1 and a deepest hole at 0.71 Å from Ag1, but was otherwise featureless.

Figures

Fig. 1.
A view of the AgI coordination environment in the polymeric structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii [Symmetry code: (i) ...
Fig. 2.
A ball and stick diagram showing the one-dimensional chain. All counteranions and H atoms have been omitted for clarity.
Fig. 3.
A diagram showing the intermolecular hydrogen bonds, indicated by dashed lines.

Crystal data

[Ag(C14H10N4O)2]PF6F000 = 3008
Mr = 753.36Dx = 1.674 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5745 reflections
a = 22.3252 (17) Åθ = 2.1–27.5º
b = 13.6939 (11) ŵ = 0.81 mm1
c = 19.8523 (16) ÅT = 173 (2) K
β = 99.9770 (10)ºPrism, colourless
V = 5977.4 (8) Å30.44 × 0.32 × 0.29 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer6823 independent reflections
Radiation source: fine-focus sealed tube5105 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 173(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Siemens, 1996)h = −28→25
Tmin = 0.718, Tmax = 0.800k = −16→17
19020 measured reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099  w = 1/[σ2(Fo2) + (0.0457P)2 + 5.9377P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6823 reflectionsΔρmax = 0.92 e Å3
460 parametersΔρmin = −0.67 e Å3
96 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/UeqOcc. (<1)
N80.61351 (13)0.7668 (2)−0.23514 (14)0.0680 (8)
C280.57801 (14)0.7655 (3)−0.20064 (15)0.0538 (7)
C250.53188 (13)0.7592 (2)−0.15834 (14)0.0478 (7)
C240.50609 (14)0.6686 (2)−0.14987 (15)0.0531 (7)
H240.51840.6128−0.17240.064*
C260.51433 (15)0.8411 (3)−0.12646 (17)0.0601 (8)
H260.53150.9031−0.13300.072*
C270.47114 (15)0.8310 (2)−0.08462 (18)0.0601 (8)
H270.45920.8868−0.06180.072*
C230.46282 (14)0.6602 (2)−0.10881 (15)0.0510 (7)
H230.44490.5985−0.10320.061*
C220.44513 (13)0.7418 (2)−0.07544 (14)0.0477 (7)
C210.40138 (14)0.7334 (2)−0.02860 (15)0.0520 (7)
H210.39600.78640.00060.062*
N70.37061 (11)0.6556 (2)−0.02684 (12)0.0494 (6)
N60.33253 (11)0.6554 (2)0.02109 (12)0.0486 (6)
Ag10.182725 (12)0.812121 (16)0.197931 (13)0.05723 (10)
C120.44862 (16)1.2299 (3)−0.09411 (17)0.0643 (9)
H120.46991.1967−0.12480.077*
C190.24057 (13)0.66761 (18)0.10608 (13)0.0401 (6)
H190.25090.72700.08620.048*
C150.19185 (13)0.5876 (2)0.18284 (14)0.0429 (6)
H150.16730.58970.21740.052*
C60.24333 (13)1.19804 (19)0.14358 (14)0.0416 (6)
C180.26109 (12)0.58116 (18)0.08291 (12)0.0367 (5)
C90.38638 (14)1.3271 (2)−0.00520 (16)0.0532 (7)
H90.36511.36080.02530.064*
C70.33364 (14)1.1743 (2)0.01789 (15)0.0502 (7)
H70.32561.10730.00760.060*
C40.20356 (12)1.13009 (19)0.17502 (13)0.0380 (6)
C170.24587 (13)0.49446 (19)0.11196 (14)0.0449 (6)
H170.25940.43360.09710.054*
C160.21082 (14)0.4979 (2)0.16270 (14)0.0486 (7)
H160.19990.43960.18340.058*
C10.13502 (14)1.0108 (2)0.24051 (14)0.0507 (7)
H10.11080.96950.26340.061*
C30.16615 (14)1.1703 (2)0.21661 (15)0.0482 (7)
H30.16471.23900.22260.058*
C50.20473 (13)1.02969 (19)0.16908 (13)0.0410 (6)
H50.23041.00180.14080.049*
C130.40755 (16)1.1802 (2)−0.06192 (17)0.0606 (8)
H130.40061.1126−0.07080.073*
C110.45847 (15)1.3286 (3)−0.08112 (17)0.0575 (8)
C80.37610 (13)1.2281 (2)−0.01660 (14)0.0485 (7)
C140.50138 (17)1.3823 (3)−0.1134 (2)0.0713 (10)
C20.13130 (14)1.1097 (2)0.24891 (16)0.0535 (8)
H20.10481.13610.27690.064*
C100.42664 (15)1.3771 (2)−0.03712 (17)0.0576 (8)
H100.43281.4450−0.02910.069*
N30.26781 (11)1.16107 (18)0.09093 (12)0.0452 (5)
N20.20658 (11)0.67179 (15)0.15560 (11)0.0417 (5)
N40.30732 (11)1.21732 (18)0.06194 (12)0.0474 (6)
N10.17155 (11)0.96955 (16)0.20120 (11)0.0443 (5)
N50.53463 (17)1.4260 (3)−0.1381 (2)0.1005 (13)
P10.37466 (4)0.89969 (6)0.14663 (5)0.0599 (2)
O20.29542 (10)0.50513 (15)−0.01052 (10)0.0563 (5)
O10.25284 (10)1.28063 (15)0.16533 (11)0.0584 (6)
C200.29779 (12)0.57604 (19)0.02673 (13)0.0409 (6)
F50.38656 (13)0.78661 (16)0.13688 (14)0.1030 (8)
F60.35972 (14)1.01041 (16)0.15169 (18)0.1254 (11)
F10.3229 (3)0.8764 (3)0.1891 (3)0.1111 (19)0.773 (8)
F20.4206 (3)0.9026 (5)0.2114 (4)0.182 (3)0.773 (8)
F30.4237 (2)0.9205 (3)0.1009 (4)0.129 (2)0.773 (8)
F40.3249 (2)0.8894 (4)0.0790 (2)0.1269 (19)0.773 (8)
F1'0.3816 (8)0.8806 (8)0.2243 (5)0.096 (5)0.227 (8)
F2'0.4440 (4)0.9236 (7)0.1569 (9)0.082 (4)0.227 (8)
F3'0.3702 (9)0.9217 (9)0.0687 (5)0.112 (5)0.227 (8)
F4'0.3055 (4)0.8774 (9)0.1384 (11)0.109 (5)0.227 (8)
H280.2574 (13)1.1069 (16)0.0696 (14)0.050 (9)*
H290.3373 (14)0.7020 (18)0.0501 (13)0.048 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N80.0642 (18)0.082 (2)0.0669 (17)−0.0083 (15)0.0370 (15)−0.0052 (15)
C280.0488 (17)0.067 (2)0.0496 (16)−0.0054 (15)0.0193 (14)−0.0023 (15)
C250.0400 (15)0.0643 (19)0.0425 (15)−0.0035 (13)0.0168 (12)−0.0011 (13)
C240.0556 (18)0.0592 (19)0.0508 (16)0.0032 (14)0.0264 (14)0.0007 (14)
C260.060 (2)0.0591 (19)0.068 (2)−0.0163 (15)0.0323 (17)−0.0065 (16)
C270.061 (2)0.057 (2)0.070 (2)−0.0081 (15)0.0337 (17)−0.0143 (16)
C230.0533 (18)0.0538 (17)0.0513 (16)−0.0046 (13)0.0241 (14)0.0040 (13)
C220.0434 (16)0.0615 (19)0.0422 (14)−0.0043 (13)0.0185 (13)0.0001 (13)
C210.0528 (18)0.0588 (19)0.0508 (16)−0.0022 (14)0.0266 (14)−0.0057 (14)
N70.0492 (14)0.0615 (15)0.0438 (13)−0.0014 (12)0.0254 (11)−0.0007 (11)
N60.0535 (15)0.0522 (15)0.0478 (13)−0.0051 (11)0.0304 (12)−0.0071 (11)
Ag10.07322 (19)0.03326 (13)0.07451 (18)0.00004 (10)0.03887 (14)−0.00591 (10)
C120.064 (2)0.075 (2)0.062 (2)0.0135 (18)0.0322 (17)0.0016 (18)
C190.0487 (16)0.0332 (13)0.0431 (14)−0.0006 (11)0.0210 (12)0.0034 (11)
C150.0494 (16)0.0379 (14)0.0468 (14)−0.0020 (11)0.0230 (13)−0.0003 (11)
C60.0461 (15)0.0332 (14)0.0469 (15)0.0052 (11)0.0122 (12)0.0029 (11)
C180.0411 (14)0.0351 (13)0.0366 (13)0.0005 (10)0.0145 (11)−0.0020 (10)
C90.0540 (18)0.0563 (19)0.0534 (17)0.0099 (14)0.0210 (14)0.0056 (14)
C70.0539 (18)0.0480 (17)0.0508 (16)−0.0006 (13)0.0151 (14)0.0028 (13)
C40.0431 (15)0.0345 (13)0.0377 (13)0.0032 (11)0.0107 (11)−0.0017 (10)
C170.0579 (18)0.0308 (13)0.0502 (15)0.0018 (12)0.0210 (13)−0.0012 (11)
C160.0652 (19)0.0339 (14)0.0519 (16)−0.0052 (13)0.0246 (14)0.0049 (12)
C10.0609 (19)0.0464 (16)0.0517 (16)−0.0040 (13)0.0294 (15)−0.0037 (13)
C30.0550 (17)0.0375 (15)0.0556 (16)0.0041 (12)0.0194 (14)−0.0086 (12)
C50.0520 (16)0.0349 (14)0.0396 (13)0.0029 (11)0.0176 (12)−0.0028 (11)
C130.069 (2)0.054 (2)0.063 (2)0.0052 (15)0.0251 (17)−0.0041 (15)
C110.0524 (18)0.067 (2)0.0578 (18)0.0096 (15)0.0222 (15)0.0139 (16)
C80.0455 (16)0.0573 (18)0.0444 (15)0.0042 (13)0.0123 (13)0.0069 (13)
C140.072 (2)0.070 (2)0.082 (2)0.0147 (18)0.041 (2)0.0162 (19)
C20.0587 (19)0.0492 (17)0.0604 (18)0.0035 (14)0.0321 (15)−0.0082 (14)
C100.0587 (19)0.0539 (19)0.0648 (19)0.0017 (14)0.0238 (16)0.0081 (15)
N30.0534 (15)0.0370 (13)0.0491 (13)−0.0059 (10)0.0197 (11)−0.0014 (10)
N20.0493 (13)0.0349 (12)0.0466 (12)0.0005 (9)0.0247 (11)0.0001 (9)
N40.0512 (14)0.0456 (13)0.0482 (13)−0.0036 (11)0.0163 (11)0.0063 (11)
N10.0579 (15)0.0331 (12)0.0463 (12)−0.0004 (10)0.0215 (11)−0.0037 (9)
N50.105 (3)0.084 (3)0.134 (3)0.009 (2)0.083 (3)0.021 (2)
P10.0625 (5)0.0379 (4)0.0841 (6)0.0022 (4)0.0261 (5)−0.0005 (4)
O20.0716 (14)0.0488 (12)0.0551 (12)0.0005 (10)0.0296 (11)−0.0130 (10)
O10.0766 (15)0.0328 (10)0.0723 (14)−0.0048 (10)0.0310 (12)−0.0021 (10)
C200.0463 (15)0.0397 (14)0.0403 (14)0.0051 (11)0.0179 (12)0.0000 (11)
F50.139 (2)0.0483 (12)0.125 (2)0.0164 (13)0.0331 (17)−0.0072 (13)
F60.142 (2)0.0447 (13)0.208 (3)0.0124 (13)0.083 (2)0.0042 (16)
F10.141 (4)0.087 (2)0.128 (4)0.010 (2)0.085 (3)0.026 (2)
F20.143 (5)0.219 (6)0.156 (5)0.022 (4)−0.051 (4)−0.062 (4)
F30.112 (4)0.094 (3)0.207 (6)−0.018 (2)0.105 (4)−0.012 (3)
F40.110 (3)0.157 (4)0.101 (3)0.006 (3)−0.017 (3)0.017 (3)
F1'0.149 (10)0.085 (7)0.064 (6)−0.010 (7)0.041 (7)0.010 (5)
F2'0.056 (5)0.065 (6)0.125 (9)−0.004 (4)0.020 (6)−0.001 (6)
F3'0.146 (11)0.099 (8)0.085 (7)0.012 (8)0.000 (7)0.021 (6)
F4'0.075 (7)0.097 (8)0.156 (11)−0.012 (5)0.020 (7)−0.009 (8)

Geometric parameters (Å, °)

N8—C281.134 (4)C9—C81.387 (4)
N8—Ag1i2.456 (3)C9—H90.9500
C28—C251.440 (4)C7—N41.279 (4)
C25—C261.378 (4)C7—C81.461 (4)
C25—C241.389 (4)C7—H70.9500
C24—C231.372 (4)C4—C51.381 (4)
C24—H240.9500C4—C31.386 (4)
C26—C271.384 (4)C17—C161.379 (4)
C26—H260.9500C17—H170.9500
C27—C221.379 (4)C16—H160.9500
C27—H270.9500C1—N11.347 (3)
C23—C221.390 (4)C1—C21.369 (4)
C23—H230.9500C1—H10.9500
C22—C211.465 (4)C3—C21.370 (4)
C21—N71.271 (4)C3—H30.9500
C21—H210.9500C5—N11.341 (3)
N7—N61.382 (3)C5—H50.9500
N6—C201.351 (4)C13—C81.397 (4)
N6—H290.853 (18)C13—H130.9500
Ag1—N12.172 (2)C11—C101.387 (4)
Ag1—N22.199 (2)C11—C141.443 (5)
Ag1—N8ii2.456 (3)C14—N51.130 (4)
C12—C131.384 (5)C2—H20.9500
C12—C111.387 (5)C10—H100.9500
C12—H120.9500N3—N41.371 (3)
C19—N21.343 (3)N3—H280.865 (18)
C19—C181.377 (3)P1—F21.500 (5)
C19—H190.9500P1—F1'1.545 (9)
C15—N21.338 (3)P1—F4'1.555 (10)
C15—C161.381 (4)P1—F61.559 (2)
C15—H150.9500P1—F2'1.560 (8)
C6—O11.216 (3)P1—F3'1.562 (9)
C6—N31.358 (3)P1—F31.564 (4)
C6—C41.495 (4)P1—F11.577 (3)
C18—C171.388 (4)P1—F51.589 (2)
C18—C201.496 (3)P1—F41.594 (4)
C9—C101.369 (4)O2—C201.216 (3)
C28—N8—Ag1i153.0 (3)C12—C13—H13119.6
N8—C28—C25177.1 (4)C8—C13—H13119.6
C26—C25—C24120.9 (3)C10—C11—C12120.1 (3)
C26—C25—C28120.5 (3)C10—C11—C14119.2 (3)
C24—C25—C28118.5 (3)C12—C11—C14120.7 (3)
C23—C24—C25119.7 (3)C9—C8—C13118.5 (3)
C23—C24—H24120.1C9—C8—C7121.3 (3)
C25—C24—H24120.1C13—C8—C7120.3 (3)
C25—C26—C27118.5 (3)N5—C14—C11178.6 (4)
C25—C26—H26120.7C1—C2—C3119.4 (3)
C27—C26—H26120.7C1—C2—H2120.3
C22—C27—C26121.4 (3)C3—C2—H2120.3
C22—C27—H27119.3C9—C10—C11120.1 (3)
C26—C27—H27119.3C9—C10—H10119.9
C24—C23—C22120.2 (3)C11—C10—H10119.9
C24—C23—H23119.9C6—N3—N4119.2 (2)
C22—C23—H23119.9C6—N3—H28126 (2)
C27—C22—C23119.2 (3)N4—N3—H28114 (2)
C27—C22—C21119.7 (3)C15—N2—C19117.9 (2)
C23—C22—C21121.0 (3)C15—N2—Ag1120.36 (17)
N7—C21—C22120.4 (3)C19—N2—Ag1121.45 (17)
N7—C21—H21119.8C7—N4—N3115.7 (2)
C22—C21—H21119.8C5—N1—C1117.3 (2)
C21—N7—N6114.8 (3)C5—N1—Ag1121.31 (17)
C20—N6—N7119.3 (2)C1—N1—Ag1121.18 (18)
C20—N6—H29123 (2)F2—P1—F4'127.9 (7)
N7—N6—H29116 (2)F1'—P1—F4'89.8 (7)
N1—Ag1—N2156.22 (8)F2—P1—F692.4 (3)
N1—Ag1—N8ii109.53 (9)F1'—P1—F694.9 (5)
N2—Ag1—N8ii92.22 (9)F4'—P1—F688.7 (5)
C13—C12—C11119.3 (3)F2—P1—F2'50.8 (5)
C13—C12—H12120.3F1'—P1—F2'88.9 (7)
C11—C12—H12120.3F4'—P1—F2'178.3 (8)
N2—C19—C18123.0 (2)F6—P1—F2'90.3 (4)
N2—C19—H19118.5F2—P1—F3'139.5 (7)
C18—C19—H19118.5F1'—P1—F3'177.5 (8)
N2—C15—C16122.7 (2)F4'—P1—F3'92.5 (8)
N2—C15—H15118.7F6—P1—F3'84.2 (4)
C16—C15—H15118.7F2'—P1—F3'88.8 (7)
O1—C6—N3123.4 (3)F2—P1—F392.8 (4)
O1—C6—C4120.7 (2)F1'—P1—F3130.6 (6)
N3—C6—C4115.9 (2)F4'—P1—F3139.2 (7)
C19—C18—C17118.5 (2)F6—P1—F392.24 (19)
C19—C18—C20123.1 (2)F3'—P1—F347.2 (6)
C17—C18—C20118.4 (2)F2—P1—F190.2 (4)
C10—C9—C8121.1 (3)F1'—P1—F152.3 (6)
C10—C9—H9119.5F6—P1—F188.72 (18)
C8—C9—H9119.5F2'—P1—F1140.8 (6)
N4—C7—C8120.0 (3)F3'—P1—F1129.9 (7)
N4—C7—H7120.0F3—P1—F1176.8 (3)
C8—C7—H7120.0F2—P1—F591.5 (3)
C5—C4—C3117.9 (2)F1'—P1—F588.1 (4)
C5—C4—C6124.2 (2)F4'—P1—F588.8 (5)
C3—C4—C6117.7 (2)F6—P1—F5176.14 (19)
C16—C17—C18119.0 (2)F2'—P1—F592.2 (4)
C16—C17—H17120.5F3'—P1—F592.9 (4)
C18—C17—H17120.5F3—P1—F587.63 (19)
C17—C16—C15118.9 (2)F1—P1—F591.21 (18)
C17—C16—H16120.5F2—P1—F4176.3 (4)
C15—C16—H16120.5F1'—P1—F4139.5 (6)
N1—C1—C2122.8 (3)F4'—P1—F450.2 (7)
N1—C1—H1118.6F6—P1—F490.8 (2)
C2—C1—H1118.6F2'—P1—F4131.2 (6)
C2—C3—C4119.2 (3)F3—P1—F489.0 (3)
C2—C3—H3120.4F1—P1—F487.9 (3)
C4—C3—H3120.4F5—P1—F485.3 (2)
N1—C5—C4123.4 (2)O2—C20—N6123.8 (2)
N1—C5—H5118.3O2—C20—C18121.3 (2)
C4—C5—H5118.3N6—C20—C18114.9 (2)
C12—C13—C8120.9 (3)
C26—C25—C24—C23−0.5 (5)C12—C13—C8—C7−179.0 (3)
C28—C25—C24—C23178.8 (3)N4—C7—C8—C9−3.3 (5)
C24—C25—C26—C271.2 (5)N4—C7—C8—C13176.4 (3)
C28—C25—C26—C27−178.1 (3)N1—C1—C2—C3−0.4 (5)
C25—C26—C27—C22−1.0 (5)C4—C3—C2—C11.2 (5)
C25—C24—C23—C22−0.4 (5)C8—C9—C10—C11−0.7 (5)
C26—C27—C22—C230.2 (5)C12—C11—C10—C91.4 (5)
C26—C27—C22—C21177.6 (3)C14—C11—C10—C9−179.0 (3)
C24—C23—C22—C270.6 (5)O1—C6—N3—N42.7 (4)
C24—C23—C22—C21−176.8 (3)C4—C6—N3—N4−176.6 (2)
C27—C22—C21—N7169.9 (3)C16—C15—N2—C190.9 (4)
C23—C22—C21—N7−12.7 (5)C16—C15—N2—Ag1−173.5 (2)
C22—C21—N7—N6177.8 (3)C18—C19—N2—C15−0.6 (4)
C21—N7—N6—C20179.8 (3)C18—C19—N2—Ag1173.8 (2)
N2—C19—C18—C170.1 (4)N1—Ag1—N2—C15−169.9 (2)
N2—C19—C18—C20178.6 (3)N8ii—Ag1—N2—C15−13.3 (2)
O1—C6—C4—C5−159.2 (3)N1—Ag1—N2—C1915.9 (4)
N3—C6—C4—C520.1 (4)N8ii—Ag1—N2—C19172.5 (2)
O1—C6—C4—C316.2 (4)C8—C7—N4—N3179.3 (3)
N3—C6—C4—C3−164.5 (3)C6—N3—N4—C7172.6 (3)
C19—C18—C17—C160.1 (4)C4—C5—N1—C10.7 (4)
C20—C18—C17—C16−178.5 (3)C4—C5—N1—Ag1−173.5 (2)
C18—C17—C16—C150.2 (4)C2—C1—N1—C5−0.6 (4)
N2—C15—C16—C17−0.7 (5)C2—C1—N1—Ag1173.6 (2)
C5—C4—C3—C2−1.1 (4)N2—Ag1—N1—C5−25.6 (4)
C6—C4—C3—C2−176.9 (3)N8ii—Ag1—N1—C5179.3 (2)
C3—C4—C5—N10.2 (4)N2—Ag1—N1—C1160.4 (2)
C6—C4—C5—N1175.6 (3)N8ii—Ag1—N1—C15.3 (2)
C11—C12—C13—C8−0.1 (5)N7—N6—C20—O2−3.9 (4)
C13—C12—C11—C10−1.0 (5)N7—N6—C20—C18176.5 (2)
C13—C12—C11—C14179.5 (3)C19—C18—C20—O2−150.7 (3)
C10—C9—C8—C13−0.4 (5)C17—C18—C20—O227.8 (4)
C10—C9—C8—C7179.4 (3)C19—C18—C20—N629.0 (4)
C12—C13—C8—C90.8 (5)C17—C18—C20—N6−152.5 (3)

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H28···O2iii0.865 (18)2.15 (2)2.990 (3)162 (3)
N6—H29···F50.853 (18)2.21 (2)3.001 (4)155 (3)

Symmetry codes: (iii) −x+1/2, −y+3/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2203).

References

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