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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1769-m1770
https://doi.org/10.1107/S1600536811047908

Bis[μ-N-(pyridin-2-ylmeth­yl)pyridin-2-amine-κ2N:N′]disilver(I) bis­(tri­fluoro­methane­sulfonate)

Suk-Hee Moon,a Tae Ho Kimb* and Ki-Min Parkb*

aDepartment of Food & Nutrition, Kyungnam College of Information and Technology, Busan 617-701, Republic of Korea, and bDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang, National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, kmpark@gnu.ac.kr

(Received 4 November 2011; accepted 11 November 2011; online 16 November 2011)

In the binuclear title compound, [Ag2(C11H11N3)2](CF3O3S)2, the complex cation is centrosymmetric, with the unique Ag+ cation coordinated by two pyridine N atoms from two symmetry-related N-(pyridin-2-ylmeth­yl)pyridin-2-amine ligands in a geometry slightly distorted from linear [N—Ag—N 161.02 (7)°]. This set-up leads to the formation of a 14-membered cyclic dimer. The two pyridine rings coordinated to the Ag+ cation are tilted by 80.19 (7)° with respect to each other. Inter­molecular N—H⋯O hydrogen-bonding inter­actions between the cyclic dimer and the anion exist. A two-dimensional network parallel to the ac plane is constructed by three weak Ag⋯(O,N) inter­actions as well as an F⋯F contact of 2.890 (4) Å.

Related literature

For the synthesis of the ligand, see: Foxon et al. (2002[Foxon, S. P., Walter, O. & Schindler, S. (2002). Eur. J. Inorg. Chem. pp. 111-121.]). For the crystal structure of the free ligand, see: Moon et al. (2011[Moon, S.-H., Kim, T. H. & Park, K.-M. (2011). Acta Cryst. E67, o1355.]). For the structures of related copper complexes, see: Lee et al. (2008[Lee, S., Park, S., Kang, Y., Moon, S.-H., Lee, S. S. & Park, K.-M. (2008). Bull. Korean Chem. Soc. 28, 1811-1814.]).

[Scheme 1]

Experimental

Crystal data

  • [Ag2(C11H11N3)2](CF3O3S)2

  • Mr = 884.34

  • Triclinic, [P \overline 1]

  • a = 8.4105 (5) Å

  • b = 9.3500 (6) Å

  • c = 11.1693 (7) Å

  • α = 108.489 (1)°

  • β = 92.826 (1)°

  • γ = 116.606 (1)°

  • V = 725.58 (8) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 1.58 mm−1

  • T = 173 K

  • 0.35 × 0.35 × 0.25 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.607, Tmax = 0.693

  • 4132 measured reflections

  • 2791 independent reflections

  • 2665 reflections with I > 2σ(I)

  • Rint = 0.012
Refinement

  • R[F2 > 2σ(F2)] = 0.022

  • wR(F2) = 0.058

  • S = 1.07

  • 2791 reflections

  • 208 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Selected bond lengths (Å)

Ag1—N2i 2.1500 (19)
Ag1—N1 2.1673 (19)
Ag1—N3 2.8573 (19)
Ag1—O2 2.890 (2)
Ag1—O1ii 3.0402 (18)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3N⋯O2i 0.88 2.16 2.925 (3) 145
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536811047908/wm2556sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047908/wm2556Isup2.hkl

checkCIF report


Comment top

The dipyridyl ligand N-(pyridin-2-ylmethyl)pyridin-2-amine has been synthesized by the reaction of 2-aminopyridine and 2-pyridinecarboxaldehyde according to literature (Foxon et al., 2002) and its crystal structure was already reported by our group (Moon et al., 2011). In the reaction of the ligand and CuX (X = I and Br), two-dimensional brick-wall type coordination polymers, in which rhomboid Cu2X2 nodes interconnect the dipyridyl ligands, were obtained (Lee et al., 2008). Herein, we report the crystal structure of the title compound prepared by the reaction of silver trifluoromethanesulfonate with the dipyridyl ligand.

The binuclear cation of the title compound, [Ag2(C11H11N3)2](CF3SO3)2, is located on an inversion centre. The asymmetric unit of the compound therefore consists of a Ag+ cation, an N-(pyridin-2-ylmethyl)pyridin-2-amine ligand and a trifluoromethanesulfonate anion. The two Ag+ cations, each in a geometry slightly distorted from linear (N–Ag–N 161.02 (7)°), are coordinated by two pyridine N atoms from two symmetry-related N-(pyridine-2-ylmethyl)pyridine-2-amine ligands, leading to the formation of a centrosymmetric 14-membered cyclic dimer (Fig. 1). Two pyridine rings coordinated to the Ag+ cations are tilted by 80.19 (7)° with respect to each other.

The non-coordinated CF3SO3- anions participate in N—H···O hydrogen-bonding (Table 1, Fig. 1) and weak Ag···O interactions, as well as an F···F contact of 2.890 (4) Å. Together with another weak Ag—N contact, this leads to the construction of a two-dimensional network extending parallel to the ac plane (Fig. 2).

Related literature top

For the synthesis of the ligand, see: Foxon et al. (2002). For the crystal structure of the free ligand, see: Moon et al. (2011). For the structures of related copper complexes, see: Lee et al. (2008).

Experimental top

The ligand (N-(pyridine-2-ylmethyl)pyridine-2-amine) was synthesized according to a procedure described by Foxon et al. (2002). Crystals of the title compound suitable for X-ray analysis were obtained by vapor diffusion of diethyl ether into a DMSO solution of the white precipitate afforded by the reaction of the ligand with silver(I) trifluoromethanesulfonate in the molar ratio 1:1 in methanol.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with d(C–H) = 0.95 Å for Csp2–H, 0.88 Å for amine N–H and 0.99 Å for methylene C–H. For all H atoms Uiso(H) = 1.2Ueq(C,N).

Structure description top

The dipyridyl ligand N-(pyridin-2-ylmethyl)pyridin-2-amine has been synthesized by the reaction of 2-aminopyridine and 2-pyridinecarboxaldehyde according to literature (Foxon et al., 2002) and its crystal structure was already reported by our group (Moon et al., 2011). In the reaction of the ligand and CuX (X = I and Br), two-dimensional brick-wall type coordination polymers, in which rhomboid Cu2X2 nodes interconnect the dipyridyl ligands, were obtained (Lee et al., 2008). Herein, we report the crystal structure of the title compound prepared by the reaction of silver trifluoromethanesulfonate with the dipyridyl ligand.

The binuclear cation of the title compound, [Ag2(C11H11N3)2](CF3SO3)2, is located on an inversion centre. The asymmetric unit of the compound therefore consists of a Ag+ cation, an N-(pyridin-2-ylmethyl)pyridin-2-amine ligand and a trifluoromethanesulfonate anion. The two Ag+ cations, each in a geometry slightly distorted from linear (N–Ag–N 161.02 (7)°), are coordinated by two pyridine N atoms from two symmetry-related N-(pyridine-2-ylmethyl)pyridine-2-amine ligands, leading to the formation of a centrosymmetric 14-membered cyclic dimer (Fig. 1). Two pyridine rings coordinated to the Ag+ cations are tilted by 80.19 (7)° with respect to each other.

The non-coordinated CF3SO3- anions participate in N—H···O hydrogen-bonding (Table 1, Fig. 1) and weak Ag···O interactions, as well as an F···F contact of 2.890 (4) Å. Together with another weak Ag—N contact, this leads to the construction of a two-dimensional network extending parallel to the ac plane (Fig. 2).

For the synthesis of the ligand, see: Foxon et al. (2002). For the crystal structure of the free ligand, see: Moon et al. (2011). For the structures of related copper complexes, see: Lee et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms not involved in intermolecular interactions have been omitted for clarity. H atoms are depicted as spheres with arbitrary radii; N–H···O hydrogen bonds and Ag···O interactions are shown as dashed lines. (Symmetry code: (A) -x + 2, -y + 1, -z + 1)
[Figure 2] Fig. 2. Two-dimensional network constructed by intermolecular Ag···O and F···F interactions shown as dashed lines. H atoms have been omitted for clarity. (Symmetry codes: i) -x + 1, -y + 1, -z + 1; ii) -x + 1, -y + 1, -z)
Bis[µ-N-(pyridin-2-ylmethyl)pyridin-2-amine- κ2N:N']disilver(I) bis(trifluoromethanesulfonate) top
Crystal data top
[Ag2(C11H11N3)2](CF3O3S)2Z = 1
Mr = 884.34F(000) = 436
Triclinic, P1Dx = 2.024 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4105 (5) ÅCell parameters from 3938 reflections
b = 9.3500 (6) Åθ = 2.7–28.3°
c = 11.1693 (7) ŵ = 1.58 mm−1
α = 108.489 (1)°T = 173 K
β = 92.826 (1)°Block, colorless
γ = 116.606 (1)°0.35 × 0.35 × 0.25 mm
V = 725.58 (8) Å3
Data collection top
Bruker APEXII CCD
diffractometer		2791 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
φ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→10
Tmin = 0.607, Tmax = 0.693k = −11→8
4132 measured reflectionsl = −11→13
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)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0304P)2 + 0.5885P]
where P = (Fo2 + 2Fc2)/3
2791 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
[Ag2(C11H11N3)2](CF3O3S)2γ = 116.606 (1)°
Mr = 884.34V = 725.58 (8) Å3
Triclinic, P1Z = 1
a = 8.4105 (5) ÅMo Kα radiation
b = 9.3500 (6) ŵ = 1.58 mm−1
c = 11.1693 (7) ÅT = 173 K
α = 108.489 (1)°0.35 × 0.35 × 0.25 mm
β = 92.826 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		2791 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2665 reflections with I > 2σ(I)
Tmin = 0.607, Tmax = 0.693Rint = 0.012
4132 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.058H-atom parameters constrained
S = 1.07Δρmax = 0.52 e Å−3
2791 reflectionsΔρmin = −0.58 e Å−3
208 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.

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
Ag10.73116 (2)0.42494 (2)0.529910 (17)0.02835 (8)
S10.71713 (7)0.57867 (7)0.27669 (5)0.02346 (13)
F10.7558 (2)0.4025 (2)0.05757 (16)0.0470 (4)
F20.4881 (2)0.3730 (2)0.05173 (16)0.0458 (4)
F30.5706 (3)0.2439 (2)0.14581 (17)0.0472 (4)
O10.5669 (3)0.5441 (3)0.33935 (19)0.0453 (5)
O20.8665 (3)0.5741 (3)0.34139 (18)0.0401 (4)
O30.7701 (3)0.7179 (2)0.2327 (2)0.0432 (5)
N10.5191 (2)0.1705 (2)0.40024 (18)0.0208 (4)
N21.0963 (2)0.3571 (2)0.29514 (18)0.0214 (4)
N30.8870 (2)0.2190 (2)0.40206 (18)0.0233 (4)
H3N0.94690.31250.47320.028*
C10.3513 (3)0.1454 (3)0.3606 (2)0.0246 (5)
H10.33030.24130.38820.030*
C20.2088 (3)−0.0146 (3)0.2816 (2)0.0276 (5)
H20.0916−0.02880.25610.033*
C30.2397 (3)−0.1544 (3)0.2398 (2)0.0290 (5)
H30.1438−0.26610.18590.035*
C40.4122 (3)−0.1284 (3)0.2781 (2)0.0256 (5)
H40.4370−0.22190.24940.031*
C50.5496 (3)0.0359 (3)0.3591 (2)0.0201 (4)
C60.7364 (3)0.0649 (3)0.4082 (2)0.0230 (4)
H6A0.74810.07380.49920.028*
H6B0.7467−0.03720.35660.028*
C70.9368 (3)0.2208 (3)0.2875 (2)0.0195 (4)
C80.8283 (3)0.0890 (3)0.1673 (2)0.0236 (5)
H80.7182−0.00830.16310.028*
C90.8834 (3)0.1027 (3)0.0562 (2)0.0264 (5)
H90.81010.0155−0.02570.032*
C101.0466 (3)0.2440 (3)0.0629 (2)0.0271 (5)
H101.08640.2556−0.01330.033*
C111.1477 (3)0.3658 (3)0.1834 (2)0.0259 (5)
H111.26010.46180.18890.031*
C120.6282 (3)0.3897 (3)0.1256 (2)0.0265 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.02417 (11)0.01720 (10)0.02998 (12)0.00595 (8)−0.00098 (7)−0.00025 (7)
S10.0221 (3)0.0213 (3)0.0212 (3)0.0091 (2)0.0029 (2)0.0037 (2)
F10.0484 (10)0.0486 (10)0.0368 (9)0.0236 (9)0.0216 (8)0.0059 (8)
F20.0425 (9)0.0494 (10)0.0325 (8)0.0217 (8)−0.0096 (7)0.0038 (7)
F30.0636 (11)0.0233 (8)0.0445 (10)0.0155 (8)0.0077 (8)0.0098 (7)
O10.0343 (10)0.0484 (12)0.0359 (11)0.0150 (9)0.0156 (9)0.0019 (9)
O20.0359 (10)0.0451 (11)0.0313 (10)0.0205 (9)−0.0062 (8)0.0060 (9)
O30.0574 (13)0.0234 (9)0.0423 (11)0.0160 (9)0.0063 (10)0.0111 (8)
N10.0211 (9)0.0183 (9)0.0192 (9)0.0073 (7)0.0041 (7)0.0062 (7)
N20.0179 (9)0.0175 (9)0.0250 (10)0.0079 (7)0.0044 (7)0.0048 (7)
N30.0200 (9)0.0216 (9)0.0193 (9)0.0063 (8)0.0029 (7)0.0030 (7)
C10.0248 (11)0.0261 (12)0.0235 (11)0.0126 (10)0.0051 (9)0.0098 (9)
C20.0220 (11)0.0331 (13)0.0226 (11)0.0095 (10)0.0023 (9)0.0107 (10)
C30.0258 (12)0.0233 (12)0.0222 (11)0.0031 (10)0.0018 (9)0.0036 (9)
C40.0285 (12)0.0187 (11)0.0238 (11)0.0088 (9)0.0072 (9)0.0050 (9)
C50.0232 (10)0.0191 (10)0.0173 (10)0.0084 (9)0.0070 (8)0.0090 (8)
C60.0250 (11)0.0224 (11)0.0225 (11)0.0116 (9)0.0065 (9)0.0096 (9)
C70.0173 (10)0.0188 (10)0.0218 (11)0.0102 (8)0.0039 (8)0.0051 (9)
C80.0192 (10)0.0209 (11)0.0236 (11)0.0063 (9)0.0041 (9)0.0054 (9)
C90.0250 (11)0.0274 (12)0.0201 (11)0.0109 (10)0.0021 (9)0.0043 (9)
C100.0285 (12)0.0284 (12)0.0242 (11)0.0131 (10)0.0100 (9)0.0104 (10)
C110.0232 (11)0.0239 (11)0.0304 (12)0.0112 (9)0.0094 (9)0.0101 (10)
C120.0278 (11)0.0250 (12)0.0232 (11)0.0117 (10)0.0046 (9)0.0071 (9)
Geometric parameters (Å, º) top
Ag1—N2i2.1500 (19)C1—C21.381 (3)
Ag1—N12.1673 (19)C1—H10.9500
Ag1—N32.8573 (19)C2—C31.386 (4)
Ag1—O22.890 (2)C2—H20.9500
Ag1—C11i3.006 (2)C3—C41.380 (3)
Ag1—O1ii3.0402 (18)C3—H30.9500
S1—O31.429 (2)C4—C51.393 (3)
S1—O11.4337 (19)C4—H40.9500
S1—O21.4420 (19)C5—C61.511 (3)
S1—C121.825 (2)C6—H6A0.9900
F1—C121.329 (3)C6—H6B0.9900
F2—C121.323 (3)C7—C81.406 (3)
F3—C121.327 (3)C7—Ag1i3.131 (2)
O1—Ag1ii3.0402 (18)C8—C91.369 (3)
N1—C51.340 (3)C8—H80.9500
N1—C11.348 (3)C9—C101.392 (3)
N2—C71.349 (3)C9—H90.9500
N2—C111.355 (3)C10—C111.371 (3)
N2—Ag1i2.1500 (19)C10—H100.9500
N3—C71.369 (3)C11—Ag1i3.006 (2)
N3—C61.456 (3)C11—H110.9500
N3—H3N0.8800
N2i—Ag1—N1161.02 (7)C5—C4—H4120.3
N2i—Ag1—N3115.71 (6)N1—C5—C4121.6 (2)
N1—Ag1—N369.45 (6)N1—C5—C6118.06 (19)
N2i—Ag1—O299.53 (6)C4—C5—C6120.3 (2)
N1—Ag1—O299.40 (6)C4—C5—Ag1158.27 (17)
N3—Ag1—O279.27 (6)C6—C5—Ag181.36 (12)
N2i—Ag1—O1ii81.91 (6)N3—C6—C5114.20 (18)
N1—Ag1—O1ii86.40 (6)N3—C6—Ag162.26 (11)
N3—Ag1—O1ii149.79 (6)C5—C6—Ag171.08 (12)
O2—Ag1—O1ii123.91 (6)N3—C6—H6A108.7
C11i—Ag1—O1ii64.92 (6)C5—C6—H6A108.7
O3—S1—O1116.39 (14)Ag1—C6—H6A83.1
O3—S1—O2114.82 (13)N3—C6—H6B108.7
O1—S1—O2113.51 (13)C5—C6—H6B108.7
O3—S1—C12102.74 (12)Ag1—C6—H6B168.3
O1—S1—C12104.03 (12)H6A—C6—H6B107.6
O2—S1—C12102.98 (11)N2—C7—N3116.50 (19)
S1—O1—Ag1ii162.63 (14)N2—C7—C8121.1 (2)
S1—O2—Ag1106.35 (10)N3—C7—C8122.42 (19)
C5—N1—C1118.76 (19)N3—C7—Ag1i82.48 (12)
C5—N1—Ag1121.61 (15)C8—C7—Ag1i155.01 (15)
C1—N1—Ag1119.63 (15)C9—C8—C7119.2 (2)
C7—N2—C11118.19 (19)C9—C8—H8120.4
C7—N2—Ag1i125.35 (15)C7—C8—H8120.4
C11—N2—Ag1i116.27 (15)C8—C9—C10120.2 (2)
C7—N3—C6121.04 (18)C8—C9—H9119.9
C7—N3—H3N119.5C10—C9—H9119.9
C6—N3—H3N119.5C11—C10—C9117.6 (2)
N1—C1—C2122.4 (2)C11—C10—H10121.2
C2—C1—Ag1160.26 (18)C9—C10—H10121.2
N1—C1—H1118.8N2—C11—C10123.7 (2)
C2—C1—H1118.8C10—C11—Ag1i163.26 (17)
Ag1—C1—H180.9N2—C11—H11118.1
C1—C2—C3118.9 (2)C10—C11—H11118.1
C1—C2—H2120.5Ag1i—C11—H1178.4
C3—C2—H2120.5F2—C12—F3106.8 (2)
C4—C3—C2118.8 (2)F2—C12—F1107.4 (2)
C4—C3—H3120.6F3—C12—F1107.8 (2)
C2—C3—H3120.6F2—C12—S1111.64 (17)
C3—C4—C5119.5 (2)F3—C12—S1112.18 (17)
C3—C4—H4120.3F1—C12—S1110.72 (17)
N2i—Ag1—N1—C5−89.5 (3)Ag1i—N2—C7—C8176.29 (16)
N2i—Ag1—N1—C189.7 (3)C6—N3—C7—N2−168.59 (19)
C5—N1—C1—C21.4 (3)C6—N3—C7—C811.8 (3)
Ag1—N1—C1—C2−177.83 (17)N2—C7—C8—C9−2.1 (3)
N1—C1—C2—C3−0.8 (4)N3—C7—C8—C9177.5 (2)
C1—C2—C3—C4−0.5 (4)C7—C8—C9—C101.2 (4)
C2—C3—C4—C51.2 (3)C8—C9—C10—C110.3 (4)
C1—N1—C5—C4−0.6 (3)C7—N2—C11—C100.1 (3)
Ag1—N1—C5—C4178.56 (16)Ag1i—N2—C11—C10−175.23 (19)
C1—N1—C5—C6−177.88 (19)C9—C10—C11—N2−0.9 (4)
Ag1—N1—C5—C61.3 (3)O3—S1—C12—F2−60.1 (2)
C3—C4—C5—N1−0.6 (3)O1—S1—C12—F261.6 (2)
C3—C4—C5—C6176.6 (2)O2—S1—C12—F2−179.73 (18)
C7—N3—C6—C5−77.7 (3)O3—S1—C12—F3−179.98 (18)
N1—C5—C6—N3−46.9 (3)O1—S1—C12—F3−58.2 (2)
C4—C5—C6—N3135.8 (2)O2—S1—C12—F360.4 (2)
C11—N2—C7—N3−178.18 (19)O3—S1—C12—F159.5 (2)
Ag1i—N2—C7—N3−3.3 (3)O1—S1—C12—F1−178.74 (19)
C11—N2—C7—C81.4 (3)O2—S1—C12—F1−60.1 (2)
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O2i0.882.162.925 (3)145
Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[Ag2(C11H11N3)2](CF3O3S)2
Mr884.34
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.4105 (5), 9.3500 (6), 11.1693 (7)
α, β, γ (°)108.489 (1), 92.826 (1), 116.606 (1)
V (Å3)725.58 (8)
Z1
Radiation typeMo Kα
µ (mm−1)1.58
Crystal size (mm)0.35 × 0.35 × 0.25
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.607, 0.693
No. of measured, independent and
observed [I > 2σ(I)] reflections		4132, 2791, 2665
Rint0.012
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.058, 1.07
No. of reflections2791
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.52, −0.58

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Selected bond lengths (Å) top
Ag1—N2i2.1500 (19)Ag1—O22.890 (2)
Ag1—N12.1673 (19)Ag1—O1ii3.0402 (18)
Ag1—N32.8573 (19)
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O2i0.882.162.925 (3)144.8
Symmetry code: (i) −x+2, −y+1, −z+1.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011–0006413).

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFoxon, S. P., Walter, O. & Schindler, S. (2002). Eur. J. Inorg. Chem. pp. 111–121.  CSD CrossRef Google Scholar
 First citationLee, S., Park, S., Kang, Y., Moon, S.-H., Lee, S. S. & Park, K.-M. (2008). Bull. Korean Chem. Soc. 28, 1811–1814.  Google Scholar
 First citationMoon, S.-H., Kim, T. H. & Park, K.-M. (2011). Acta Cryst. E67, o1355.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1769-m1770
https://doi.org/10.1107/S1600536811047908
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