supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, m1618-m1619    [ doi:10.1107/S1600536808038907 ]

catena-Poly[[[N'-(4-cyanobenzylidene)nicotinohydrazide)silver(I)]-[mu]-N'-(4-cyanobenzylidene)nicotinohydrazide] hexafluoridophosphate]

X.-S. Wan, Y.-L. Dang, C.-H. Kou, Z.-F. Zhou and C.-Y. Niu

Abstract top

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 [\overline{1}01]. 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).

Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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) x - 1/2, -y + 3/2, z + 1/2].
[Figure 2] Fig. 2. A ball and stick diagram showing the one-dimensional chain. All counteranions and H atoms have been omitted for clarity.
[Figure 3] Fig. 3. A diagram showing the intermolecular hydrogen bonds, indicated by dashed lines.
catena-Poly[[[N'-(4-cyanobenzylidene)nicotinohydrazide)silver(I)]-µ- N'-(4-cyanobenzylidene)nicotinohydrazide] hexafluorophosphate] top
Crystal data top
[Ag(C14H10N4O)2]PF6F(000) = 3008
Mr = 753.36Dx = 1.674 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5745 reflections
a = 22.3252 (17) Åθ = 2.1–27.5°
b = 13.6939 (11) ŵ = 0.81 mm−1
c = 19.8523 (16) ÅT = 173 K
β = 99.977 (1)°Prism, colourless
V = 5977.4 (8) Å30.44 × 0.32 × 0.29 mm
Z = 8
Data collection top
Siemens SMART CCD area-detector
diffractometer		6823 independent reflections
Radiation source: fine-focus sealed tube5105 reflections with I > 2σ(I)
graphiteRint = 0.022
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)		h = −28→25
Tmin = 0.718, Tmax = 0.800k = −16→17
19020 measured reflectionsl = −25→25
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0457P)2 + 5.9377P]
where P = (Fo2 + 2Fc2)/3
6823 reflections(Δ/σ)max = 0.001
460 parametersΔρmax = 0.92 e Å−3
96 restraintsΔρmin = −0.67 e Å−3
Crystal data top
[Ag(C14H10N4O)2]PF6V = 5977.4 (8) Å3
Mr = 753.36Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.3252 (17) ŵ = 0.81 mm−1
b = 13.6939 (11) ÅT = 173 K
c = 19.8523 (16) Å0.44 × 0.32 × 0.29 mm
β = 99.977 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer		6823 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1996)		5105 reflections with I > 2σ(I)
Tmin = 0.718, Tmax = 0.800Rint = 0.022
19020 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099Δρmax = 0.92 e Å−3
S = 1.03Δρmin = −0.67 e Å−3
6823 reflectionsAbsolute structure: ?
460 parametersFlack parameter: ?
96 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
D—H···AD—HH···AD···AD—H···A
N3—H28···O2iii0.87 (2)2.15 (2)2.990 (3)162 (3)
N6—H29···F50.85 (2)2.21 (2)3.001 (4)155 (3)
Symmetry codes: (iii) −x+1/2, −y+3/2, −z.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N12.172 (2)Ag1—N8i2.456 (3)
Ag1—N22.199 (2)
N1—Ag1—N2156.22 (8)N2—Ag1—N8i92.22 (9)
N1—Ag1—N8i109.53 (9)
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H28···O2ii0.87 (2)2.15 (2)2.990 (3)162 (3)
N6—H29···F50.85 (2)2.21 (2)3.001 (4)155 (3)
Symmetry codes: (ii) −x+1/2, −y+3/2, −z.
Acknowledgements top

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).

references
References top

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Dong, Y.-B., Zhao, X., Huang, R.-Q., Smith, M. D. & Zur Loye, H.-S. (2004). Inorg. Chem. 43, 5603–5612.

Niu, C.-Y., Wu, B.-L., Zheng, X.-F., Zhang, H.-Y., Li, Z.-J. & Hou, H.-W. (2007). Dalton Trans. pp. 5710–5713.

Niu, C.-Y., Zheng, X.-F., Bai, L.-L., Wu, X.-L. & Kou, C.-H. (2008). Acta Cryst. C64, m305–m307.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sumby, C. J. & Hardie, M. J. (2005). Angew. Chem. Int. Ed. 44, 6395–6399.

Vatsadze, S. Z., Kovalkina, M. A., Sviridenkova, N. V., Zyk, N. V., Churakov, A. V., Kuz'mina, L. G. & Howard, J. A. K. (2004). CrystEngComm, 6, 112–115.

Zheng, Y., Du, M., Li, J.-R., Zhang, R.-H. & Bu, X.-H. (2003). Dalton Trans. pp. 1509–1514.