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The title compound, [Ag(CF3O3S)(C10H9N3)]n, is a chain polymer in which neighbouring monomeric units are related by a glide plane. The silver centre is four-coordinate; the donor atoms are one trifluoro­methane­sulfonate O atom and one pyridine N atom from each of two symmetry-related dipyridylamines, and an additional and unexpected Ag...C contact [2.6464 (16) Å] is observed to a pyridine C atom. The chains are reinforced by one classical N—H...O and two `weak' C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106028009/gd3040sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106028009/gd3040Isup2.hkl
Contains datablock I

CCDC reference: 621259

Comment top

We are interested in complexes of the ligand 2,2'-dipyridylamine (DPA), and have reported some of its complexes with silver, gold and palladium, together with the structure of [(DPA)(PPh3)Ag](OTf) (OTf is trifluoromethanesulfonate; Burgos et al., 2003). This displays, to a first approximation, three-coordinate silver, the donor atoms being the P atom (of PPh3) and both pyridine N atoms of the same DPA ligand. An additional Ag···O interaction of 2.725 (3) Å, supported by an N—H···O hydrogen bond, links the molecules to form chains. The synthesis of the title compound [(DPA)Ag(Otf)], (I), was reported at the time, but not the structure, which we present here.

The asymmetric unit is presented in Fig. 1. It is striking that the compound does not display the structure of a simple molecule [(DPA)Ag(OTf)], with coordination through the pyridine N atoms and a trifluoromethanesulfonate O atom, as might perhaps have been expected. Instead, coordination occurs via one pyridine N atom (N11), the trifluoromethanesulfonate atom O3 and the second pyridine N atom (N21) of a different asymmetric unit (the latter not shown in Fig. 1; the extended structure is discussed below). The Ag—N distances (Table 1) are broadly similar to those of [(DPA)(PPh3)Ag](OTf) [Ag—N = 2.264 (2) and 2.283 (2) Å], but the Ag—O distance is appreciably shorter and may be assumed to correspond to a stronger bonding interaction.

Within the asymmetric unit there is also an unexpected contact from silver to a ring C atom, namely Ag···C23, approximately perpendicular to the ring (the angle between the vector Ag···C23 and the mean ring plane is 70.7°). In contrast to the more familiar situation, for example, in the complex of silver perchlorate and benzene [Ag—C = 2.565 (1) Å in a low-temperature neutron study (McMullan et al., 1997)], the silver is coordinated to just this one C atom, rather than at equal distances to two neighbouring ring C atoms; the distances to atoms C22 and C24 are much greater at 3.049 (2) and 3.260 (2) Å respectively. There are difficulties involved in searching the Cambridge Structural Database (Version 5.27; Allen, 2002) for such contacts (are they coded as bonds or not?), but we were unable to find a further example of such a short contact involving a pyridine ligand.

The dimensions of the DPA ligand may be regarded as normal, although the N11—C12 bond is somewhat short at 1.337 (2) Å. The interplanar angle between the rings is 34.60 (5)°. More informative are the torsion angles N11—C12—N1—C22 and N21—C22—N1—C12 (Table 1), which are very approximately syn- and antiperiplanar, respectively. The additional contact to the Ag atom results in no significant changes to the dimensions of the ring N21/C22–C26.

The extended structure most importantly involves an Ag—N21 bond to a neighbouring molecule generated by the n-glide plane. This leads to four-coordination at the Ag atom and to the formation of a chain polymer parallel to the y axis (Fig. 2). Within this polymer, one classical N—H···O hydrogen bond and two `weak' C—H···O interactions (Desiraju & Steiner, 1999) (the first three hydrogen bonds of Table 2), including a bifurcated system involving the common acceptor O2, presumably act as stabilizing features; a long Ag···O1 contact within the chain [3.2079 (14) Å] is probably less relevant and is not included in the figure. There are short C—H···X (X = O and F) contacts (Table 2) between neighbouring chains.

Experimental top

The complex was synthesized as described by Burgos et al. (2003) and recrystallized from dichloromethane/pentane.

Refinement top

The amine H atom was refined freely but with an N—H bond length restraint [N—H = ? (?) Å]. Other H atoms were included using a riding model with fixed C—H bond lengths of 0.95 Å; Uiso(H) values were fixed at 1.2Ueq of the parent atom.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound in the crystal. Dispalcement ellipsoids represent 50% probability levels.
[Figure 2] Fig. 2. Packing diagram of one the title compound, viewed perpendicular to the xy plane. Secondary interactions are indicated by dashed lines (thick, N—H···O bonds; thin, C—H···O bonds). The origin is at the lower right-hand corner, with the x and y axes drawn vertically and horizontally respectively.
catena-Poly[[(trifluoromethanesulfonato-κO)silver(I)]-µ-di-2- pyridylamine-κ2N2:N2'] top
Crystal data top
[Ag(CF3O3S)(C10H9N3)]F(000) = 840
Mr = 428.14Dx = 2.060 Mg m3
MonoclinicP21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8192 reflections
a = 10.9077 (8) Åθ = 2–28°
b = 9.9610 (6) ŵ = 1.66 mm1
c = 13.2994 (8) ÅT = 143 K
β = 107.223 (3)°Tablet, colourless
V = 1380.21 (16) Å30.21 × 0.10 × 0.04 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer
4029 independent reflections
Radiation source: fine-focus sealed tube3394 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.192 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω and φ scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 1313
Tmin = 0.803, Tmax = 0.936l = 1818
22658 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0348P)2]
where P = (Fo2 + 2Fc2)/3
4029 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.71 e Å3
1 restraintΔρmin = 0.47 e Å3
Crystal data top
[Ag(CF3O3S)(C10H9N3)]V = 1380.21 (16) Å3
Mr = 428.14Z = 4
MonoclinicP21/nMo Kα radiation
a = 10.9077 (8) ŵ = 1.66 mm1
b = 9.9610 (6) ÅT = 143 K
c = 13.2994 (8) Å0.21 × 0.10 × 0.04 mm
β = 107.223 (3)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
4029 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
3394 reflections with I > 2σ(I)
Tmin = 0.803, Tmax = 0.936Rint = 0.050
22658 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0241 restraint
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.71 e Å3
4029 reflectionsΔρmin = 0.47 e Å3
203 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.9775 (0.0069) x + 2.4802 (0.0069) y + 12.8336 (0.0027) z = 1.6896 (0.0032)

* -0.0184 (0.0011) N11 * 0.0241 (0.0011) C12 * -0.0089 (0.0012) C13 * -0.0110 (0.0012) C14 * 0.0165 (0.0012) C15 * -0.0023 (0.0012) C16

Rms deviation of fitted atoms = 0.0152

- 3.8667 (0.0073) x - 3.4362 (0.0063) y + 12.4361 (0.0033) z = 1.0645 (0.0065)

Angle to previous plane (with approximate e.s.d.) = 34.60 (0.05)

* -0.0041 (0.0011) N21 * -0.0147 (0.0011) C22 * 0.0198 (0.0011) C23 * -0.0073 (0.0012) C24 * -0.0113 (0.0013) C25 * 0.0176 (0.0012) C26

Rms deviation of fitted atoms = 0.0136

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag0.654332 (12)0.417932 (13)0.205239 (11)0.02513 (5)
N10.60359 (12)0.11452 (14)0.30346 (11)0.0169 (3)
H10.6066 (18)0.0353 (16)0.3053 (15)0.017 (5)*
N110.48176 (12)0.30023 (14)0.22151 (11)0.0183 (3)
C120.48602 (14)0.17155 (17)0.25101 (12)0.0166 (3)
C130.37563 (15)0.09087 (17)0.22982 (13)0.0205 (3)
H130.38180.00160.24800.025*
C140.25813 (15)0.1491 (2)0.18198 (14)0.0246 (4)
H140.18190.09700.16690.029*
C150.25188 (15)0.2852 (2)0.15588 (14)0.0246 (4)
H150.17170.32800.12520.029*
C160.36476 (15)0.35545 (18)0.17583 (13)0.0219 (3)
H160.36080.44760.15670.026*
N210.82469 (13)0.10918 (14)0.37185 (11)0.0174 (3)
C220.71549 (14)0.18078 (16)0.35683 (12)0.0160 (3)
C230.71650 (15)0.31159 (17)0.39606 (13)0.0189 (3)
H230.63840.35860.38810.023*
C240.83336 (16)0.37096 (19)0.44662 (13)0.0228 (3)
H240.83630.46080.47110.027*
C250.94608 (16)0.29875 (19)0.46140 (14)0.0254 (4)
H251.02720.33780.49560.030*
C260.93652 (15)0.16893 (19)0.42487 (14)0.0227 (3)
H261.01320.11800.43770.027*
S0.86705 (4)0.21888 (4)0.12677 (3)0.01708 (8)
C10.84934 (17)0.2596 (2)0.01049 (14)0.0302 (4)
O10.93431 (13)0.09288 (12)0.14354 (11)0.0272 (3)
O20.93863 (12)0.33110 (13)0.18348 (10)0.0272 (3)
O30.73477 (11)0.21333 (14)0.12852 (10)0.0257 (3)
F10.78059 (14)0.16751 (18)0.07471 (10)0.0544 (4)
F20.79006 (14)0.37703 (16)0.03641 (11)0.0506 (4)
F30.96306 (12)0.26783 (17)0.02798 (10)0.0502 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag0.02244 (7)0.01877 (8)0.03667 (9)0.00211 (5)0.01257 (5)0.00529 (5)
N10.0142 (6)0.0116 (7)0.0235 (7)0.0002 (5)0.0035 (5)0.0002 (5)
N110.0137 (6)0.0180 (7)0.0232 (7)0.0017 (5)0.0055 (5)0.0013 (5)
C120.0143 (7)0.0179 (8)0.0179 (7)0.0001 (5)0.0054 (5)0.0010 (6)
C130.0178 (7)0.0189 (8)0.0244 (8)0.0038 (6)0.0056 (6)0.0005 (6)
C140.0147 (7)0.0308 (10)0.0276 (9)0.0045 (6)0.0053 (6)0.0024 (7)
C150.0154 (7)0.0298 (10)0.0268 (9)0.0048 (6)0.0035 (6)0.0008 (7)
C160.0185 (7)0.0205 (9)0.0258 (8)0.0044 (6)0.0052 (6)0.0026 (6)
N210.0152 (6)0.0175 (7)0.0189 (6)0.0016 (5)0.0042 (5)0.0001 (5)
C220.0161 (7)0.0162 (8)0.0155 (7)0.0006 (5)0.0044 (5)0.0014 (5)
C230.0189 (7)0.0172 (8)0.0200 (7)0.0013 (6)0.0050 (6)0.0003 (6)
C240.0256 (8)0.0175 (8)0.0236 (8)0.0038 (6)0.0047 (6)0.0024 (6)
C250.0190 (8)0.0245 (10)0.0283 (9)0.0047 (6)0.0003 (6)0.0017 (7)
C260.0157 (7)0.0250 (9)0.0255 (8)0.0012 (6)0.0032 (6)0.0005 (7)
S0.01620 (17)0.01458 (19)0.02056 (18)0.00013 (13)0.00561 (13)0.00044 (14)
C10.0240 (8)0.0421 (12)0.0250 (9)0.0016 (8)0.0083 (7)0.0025 (8)
O10.0268 (6)0.0158 (7)0.0396 (7)0.0027 (5)0.0109 (5)0.0012 (5)
O20.0258 (6)0.0178 (6)0.0333 (7)0.0018 (5)0.0016 (5)0.0051 (5)
O30.0187 (6)0.0305 (7)0.0301 (6)0.0007 (5)0.0104 (5)0.0014 (5)
F10.0530 (8)0.0786 (12)0.0276 (6)0.0120 (8)0.0058 (6)0.0184 (7)
F20.0524 (8)0.0562 (9)0.0427 (7)0.0201 (7)0.0136 (6)0.0279 (7)
F30.0319 (6)0.0884 (12)0.0369 (7)0.0030 (7)0.0202 (5)0.0142 (7)
Geometric parameters (Å, º) top
Ag—N21i2.2072 (14)N21—C221.351 (2)
Ag—N112.2817 (13)N21—C261.353 (2)
Ag—O32.5484 (13)C22—C231.402 (2)
Ag—C232.6464 (16)C23—C241.385 (2)
N1—C221.384 (2)C23—H230.9500
N1—C121.387 (2)C24—C251.387 (2)
N1—H10.790 (15)C24—H240.9500
N11—C121.337 (2)C25—C261.374 (3)
N11—C161.357 (2)C25—H250.9500
C12—C131.405 (2)C26—H260.9500
C13—C141.379 (2)S—O11.4375 (13)
C13—H130.9500S—O21.4420 (13)
C14—C151.396 (3)S—O31.4510 (12)
C14—H140.9500S—C11.8234 (19)
C15—C161.372 (2)C1—F11.324 (2)
C15—H150.9500C1—F31.330 (2)
C16—H160.9500C1—F21.332 (3)
N21i—Ag—N11133.59 (5)N21—C22—C23121.73 (14)
N21i—Ag—O3114.14 (5)N1—C22—C23122.84 (14)
N11—Ag—O391.06 (4)C24—C23—C22118.81 (15)
N21i—Ag—C23139.34 (5)C24—C23—Ag103.43 (11)
N11—Ag—C2371.80 (5)C22—C23—Ag92.50 (10)
O3—Ag—C2392.46 (5)C24—C23—H23120.6
C22—N1—C12127.31 (14)C22—C23—H23120.6
C22—N1—H1116.0 (14)Ag—C23—H2374.3
C12—N1—H1116.7 (14)C23—C24—C25119.80 (17)
C12—N11—C16117.80 (14)C23—C24—H24120.1
C12—N11—Ag124.22 (10)C25—C24—H24120.1
C16—N11—Ag116.24 (11)C26—C25—C24117.80 (15)
N11—C12—N1119.13 (14)C26—C25—H25121.1
N11—C12—C13122.42 (14)C24—C25—H25121.1
N1—C12—C13118.45 (15)N21—C26—C25124.09 (16)
C14—C13—C12118.43 (16)N21—C26—H26118.0
C14—C13—H13120.8C25—C26—H26118.0
C12—C13—H13120.8O1—S—O2115.04 (8)
C13—C14—C15119.59 (16)O1—S—O3115.37 (8)
C13—C14—H14120.2O2—S—O3114.08 (8)
C15—C14—H14120.2O1—S—C1104.32 (9)
C16—C15—C14118.17 (15)O2—S—C1103.40 (9)
C16—C15—H15120.9O3—S—C1102.33 (8)
C14—C15—H15120.9F1—C1—F3108.02 (16)
N11—C16—C15123.44 (16)F1—C1—F2107.61 (16)
N11—C16—H16118.3F3—C1—F2107.86 (17)
C15—C16—H16118.3F1—C1—S111.33 (15)
C22—N21—C26117.65 (15)F3—C1—S111.15 (13)
C22—N21—Agii126.51 (11)F2—C1—S110.72 (13)
C26—N21—Agii114.86 (11)S—O3—Ag115.97 (7)
N21—C22—N1115.40 (14)
N21i—Ag—N11—C12164.26 (11)N1—C22—C23—Ag71.87 (15)
O3—Ag—N11—C1238.65 (13)N21i—Ag—C23—C2433.87 (15)
C23—Ag—N11—C1253.60 (13)N11—Ag—C23—C24170.85 (13)
N21i—Ag—N11—C160.33 (15)O3—Ag—C23—C2498.84 (12)
O3—Ag—N11—C16125.94 (12)N21i—Ag—C23—C22154.29 (9)
C23—Ag—N11—C16141.81 (13)N11—Ag—C23—C2268.73 (9)
C16—N11—C12—N1176.26 (14)O3—Ag—C23—C2221.58 (10)
Ag—N11—C12—N119.4 (2)C22—C23—C24—C252.7 (2)
C16—N11—C12—C134.5 (2)Ag—C23—C24—C25103.19 (16)
Ag—N11—C12—C13159.89 (12)C23—C24—C25—C260.3 (3)
C22—N1—C12—N1120.0 (2)C22—N21—C26—C252.1 (3)
C22—N1—C12—C13160.69 (15)Agii—N21—C26—C25167.34 (15)
N11—C12—C13—C143.6 (2)C24—C25—C26—N212.7 (3)
N1—C12—C13—C14177.09 (15)O1—S—C1—F161.63 (15)
C12—C13—C14—C150.1 (3)O2—S—C1—F1177.72 (13)
C13—C14—C15—C162.2 (3)O3—S—C1—F158.94 (16)
C12—N11—C16—C151.9 (2)O1—S—C1—F358.85 (17)
Ag—N11—C16—C15163.69 (14)O2—S—C1—F361.81 (17)
C14—C15—C16—N111.4 (3)O3—S—C1—F3179.41 (15)
C26—N21—C22—N1179.14 (14)O1—S—C1—F2178.71 (14)
Agii—N21—C22—N112.9 (2)O2—S—C1—F258.06 (15)
C26—N21—C22—C231.1 (2)O3—S—C1—F260.73 (15)
Agii—N21—C22—C23169.14 (11)O1—S—O3—Ag145.43 (8)
C12—N1—C22—N21159.64 (15)O2—S—O3—Ag8.96 (10)
C12—N1—C22—C2322.4 (2)C1—S—O3—Ag102.00 (9)
N21—C22—C23—C243.4 (2)N21i—Ag—O3—S55.92 (9)
N1—C22—C23—C24178.69 (15)N11—Ag—O3—S164.27 (8)
N21—C22—C23—Ag110.27 (14)C23—Ag—O3—S92.44 (8)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+3/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O1i0.952.463.213 (2)136
N1—H1···O2ii0.79 (2)2.11 (2)2.8739 (19)163 (2)
C13—H13···O2ii0.952.533.278 (2)136
C25—H25···O3iii0.952.483.275 (2)142
C14—H14···O1iv0.952.633.462 (2)147
C15—H15···F3iv0.952.633.372 (2)135
C16—H16···F2v0.952.603.397 (2)142
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+3/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Ag(CF3O3S)(C10H9N3)]
Mr428.14
Crystal system, space groupMonoclinicP21/n
Temperature (K)143
a, b, c (Å)10.9077 (8), 9.9610 (6), 13.2994 (8)
β (°) 107.223 (3)
V3)1380.21 (16)
Z4
Radiation typeMo Kα
µ (mm1)1.66
Crystal size (mm)0.21 × 0.10 × 0.04
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.803, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections
22658, 4029, 3394
Rint0.050
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.058, 0.99
No. of reflections4029
No. of parameters203
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.71, 0.47

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) top
Ag—N21i2.2072 (14)Ag—C232.6464 (16)
Ag—N112.2817 (13)N1—C221.384 (2)
Ag—O32.5484 (13)N1—C121.387 (2)
N21i—Ag—N11133.59 (5)N11—Ag—C2371.80 (5)
N21i—Ag—O3114.14 (5)O3—Ag—C2392.46 (5)
N11—Ag—O391.06 (4)C22—N1—C12127.31 (14)
N21i—Ag—C23139.34 (5)
C22—N1—C12—N1120.0 (2)C12—N1—C22—N21159.64 (15)
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O1i0.952.463.213 (2)136
N1—H1···O2ii0.790 (15)2.109 (16)2.8739 (19)163.2 (18)
C13—H13···O2ii0.952.533.278 (2)136
C25—H25···O3iii0.952.483.275 (2)142
C14—H14···O1iv0.952.633.462 (2)147
C15—H15···F3iv0.952.633.372 (2)135
C16—H16···F2v0.952.603.397 (2)142
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+3/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x1, y, z; (v) x+1, y+1, z.
 

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