metal-organic compounds
Bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κ2N4,N5](trifluoroacetato-κO)silver(I)
aTianjin Entry–Exit Inspection and Quarantine Bureau, Tianjin 300201, People's Republic of China, and bDisease Hospital of TianJin City, Tianjin 300201, People's Republic of China
*Correspondence e-mail: yanjiuyuan_lee@126.com
In the 10H6N4)2(CF3CO2)], there two mononuclear but slightly different complex units. In each, two κ2N:N-chelating 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands surround the AgI atom, giving an N4O square-pyramidal coordination geometry with one trifluoroacetate O atom at the apex. The difference between the two lies in the Ag—N bond lengths: in one complex, three normal [range 2.272 (5)–2.552 (5) Å] and one long [2.706 (4) Å] and in the second, two normal [2.254 (5) and 2.290 (5) Å] and two long [2.647 (5) and 2.675 (5) Å] are present. Short intermolecular F⋯F contacts [2.586 (4) Å] and weak π–π stacking interactions [minimum ring centroid separation 3.836 (5) Å] between pyridyl and pyrazinyl rings connect the complex units, forming columns which extend along the b-axis direction.
of the title compound, [Ag(CRelated literature
For metal complexes with pyridyl-based ligands, see: Wang et al. (2009); O'Keeffe & Yaghi (2012); Choudhury et al. (2002). For complexes with 5-(pyridin-2-yl)pyrazine-2-carbonitrile, see: Wang et al. (2010); Zhang & Yang (2011). For van der Waals radii, see: Pauling (1960).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker 2007); cell APEX2 and SAINT (Bruker 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812040846/zs2235sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812040846/zs2235Isup2.hkl
The 5-(2-pyridyl)-2-cyanopyrazine was obtained from a commercial source. This ligand (36.2 mg, 0.2 mmol) and AgCF3CO2 (22 mg, 0.1 mmol) were mixed and dissolved in 5 ml of acetonitrile with stirring at room temperature, giving a clear solution. After 2 hours, this solution was filtered, and the clear filtrate was allowed to stand for about 3 weeks, yielding yellow block-like crystals (32.8 mg, 56% yeild).
All the H atoms were discernible in the difference electron density maps. Nevertheless, the hydrogen atoms were placed in idealized positions and allowed to ride on the carrier atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The high Ueq value compared to neighbors for the C22 and C44 atoms of the trifluoroacetate ligand can be ascribed to the large thermal vibration of the tail of the anion at room temperature.
Data collection: APEX2 (Bruker 2007); cell
APEX2 and SAINT (Bruker 2007); data reduction: SAINT (Bruker 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).[Ag(C10H6N4)2(C2F3O2)] | F(000) = 2320 |
Mr = 585.27 | Dx = 1.740 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 254 reflections |
a = 12.5237 (16) Å | θ = 1.6–25.0° |
b = 14.9638 (18) Å | µ = 0.97 mm−1 |
c = 23.845 (3) Å | T = 298 K |
V = 4468.6 (10) Å3 | Block, yellow |
Z = 8 | 0.41 × 0.31 × 0.29 mm |
Bruker APEXII CCD area detector diffractometer | 7881 independent reflections |
Radiation source: fine-focus sealed tube | 6180 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω–scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −14→9 |
Tmin = 0.861, Tmax = 1.000 | k = −17→17 |
24472 measured reflections | l = −27→28 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0674P)2 + 4.5918P] P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.005 |
7881 reflections | Δρmax = 0.97 e Å−3 |
649 parameters | Δρmin = −0.64 e Å−3 |
10 restraints | Absolute structure: Flack (1983), 3488 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.10 (4) |
[Ag(C10H6N4)2(C2F3O2)] | V = 4468.6 (10) Å3 |
Mr = 585.27 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.5237 (16) Å | µ = 0.97 mm−1 |
b = 14.9638 (18) Å | T = 298 K |
c = 23.845 (3) Å | 0.41 × 0.31 × 0.29 mm |
Bruker APEXII CCD area detector diffractometer | 7881 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 6180 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 1.000 | Rint = 0.035 |
24472 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.129 | Δρmax = 0.97 e Å−3 |
S = 1.02 | Δρmin = −0.64 e Å−3 |
7881 reflections | Absolute structure: Flack (1983), 3488 Friedel pairs |
649 parameters | Absolute structure parameter: −0.10 (4) |
10 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.26811 (4) | 0.58972 (3) | 0.15292 (2) | 0.05751 (16) | |
N1 | 0.1564 (4) | 0.6017 (4) | 0.2421 (2) | 0.0516 (13) | |
N2 | 0.0587 (5) | 0.6226 (5) | 0.3462 (3) | 0.0758 (17) | |
N3 | 0.3706 (4) | 0.6293 (4) | 0.2287 (2) | 0.0527 (14) | |
N4 | −0.1913 (6) | 0.5499 (5) | 0.3209 (3) | 0.093 (2) | |
N5 | 0.3874 (5) | 0.6246 (6) | 0.0607 (2) | 0.079 (2) | |
N6 | 0.4762 (5) | 0.6152 (6) | −0.0451 (3) | 0.085 (2) | |
N7 | 0.1688 (5) | 0.6166 (5) | 0.0750 (2) | 0.0601 (16) | |
N8 | 0.7394 (5) | 0.6236 (7) | −0.0189 (3) | 0.109 (3) | |
O1 | 0.2973 (3) | 0.4296 (3) | 0.1556 (3) | 0.0661 (12) | |
O2 | 0.1194 (4) | 0.4314 (3) | 0.1498 (3) | 0.0742 (14) | |
C1 | 0.0527 (5) | 0.5835 (5) | 0.2491 (3) | 0.0551 (16) | |
H1A | 0.0121 | 0.5654 | 0.2185 | 0.066* | |
C2 | 0.0051 (5) | 0.5914 (5) | 0.3012 (3) | 0.0559 (17) | |
C3 | 0.1610 (7) | 0.6397 (6) | 0.3375 (3) | 0.072 (2) | |
H3A | 0.2015 | 0.6602 | 0.3676 | 0.087* | |
C4 | 0.2113 (6) | 0.6289 (4) | 0.2861 (3) | 0.0503 (16) | |
C5 | 0.3309 (6) | 0.6352 (5) | 0.2808 (3) | 0.0512 (16) | |
C6 | 0.3954 (7) | 0.6446 (6) | 0.3270 (3) | 0.074 (2) | |
H6A | 0.3657 | 0.6523 | 0.3624 | 0.089* | |
C7 | 0.5039 (7) | 0.6426 (7) | 0.3203 (3) | 0.088 (3) | |
H7A | 0.5490 | 0.6474 | 0.3512 | 0.106* | |
C8 | 0.5444 (7) | 0.6337 (6) | 0.2682 (4) | 0.080 (3) | |
H8A | 0.6178 | 0.6304 | 0.2627 | 0.096* | |
C9 | 0.4753 (6) | 0.6294 (6) | 0.2234 (3) | 0.069 (2) | |
H9A | 0.5041 | 0.6265 | 0.1874 | 0.083* | |
C10 | −0.1049 (6) | 0.5672 (5) | 0.3110 (3) | 0.069 (2) | |
C11 | 0.3254 (5) | 0.6217 (5) | 0.0158 (3) | 0.0561 (18) | |
C12 | 0.3730 (6) | 0.6163 (7) | −0.0363 (3) | 0.081 (3) | |
H12A | 0.3285 | 0.6133 | −0.0675 | 0.098* | |
C13 | 0.5371 (6) | 0.6203 (6) | 0.0005 (3) | 0.067 (2) | |
C14 | 0.4929 (6) | 0.6226 (7) | 0.0529 (3) | 0.086 (3) | |
H14A | 0.5377 | 0.6227 | 0.0840 | 0.103* | |
C15 | 0.2073 (6) | 0.6224 (5) | 0.0227 (3) | 0.0508 (16) | |
C16 | 0.1397 (7) | 0.6286 (7) | −0.0234 (3) | 0.084 (3) | |
H16A | 0.1672 | 0.6347 | −0.0594 | 0.100* | |
C17 | 0.0316 (6) | 0.6256 (8) | −0.0145 (3) | 0.084 (3) | |
H17A | −0.0151 | 0.6285 | −0.0448 | 0.101* | |
C18 | −0.0068 (6) | 0.6185 (6) | 0.0383 (3) | 0.074 (2) | |
H18A | −0.0799 | 0.6163 | 0.0452 | 0.089* | |
C19 | 0.0659 (6) | 0.6145 (7) | 0.0814 (3) | 0.074 (2) | |
H19A | 0.0394 | 0.6100 | 0.1177 | 0.089* | |
C20 | 0.6515 (6) | 0.6222 (7) | −0.0092 (3) | 0.079 (2) | |
C21 | 0.2075 (5) | 0.3957 (4) | 0.1521 (3) | 0.0519 (14) | |
C22 | 0.2084 (5) | 0.2977 (5) | 0.1513 (4) | 0.0630 (17) | |
F1 | 0.1244 (6) | 0.2588 (4) | 0.1377 (5) | 0.237 (7) | |
F2 | 0.2200 (12) | 0.2641 (5) | 0.1986 (3) | 0.257 (8) | |
F3 | 0.2781 (8) | 0.2573 (4) | 0.1263 (5) | 0.224 (6) | |
Ag2 | 0.28673 (4) | −0.10754 (3) | 0.34638 (2) | 0.05706 (16) | |
N9 | 0.1721 (5) | −0.1347 (5) | 0.4381 (2) | 0.074 (2) | |
N10 | 0.0807 (5) | −0.1065 (5) | 0.5421 (2) | 0.0752 (19) | |
N11 | 0.3892 (5) | −0.1344 (5) | 0.4241 (2) | 0.0633 (18) | |
N12 | −0.1796 (6) | −0.1231 (8) | 0.5156 (4) | 0.124 (3) | |
N13 | 0.4147 (4) | −0.1294 (4) | 0.2578 (2) | 0.0556 (15) | |
N14 | 0.5064 (5) | −0.1172 (7) | 0.1529 (3) | 0.105 (3) | |
N15 | 0.1944 (4) | −0.1402 (4) | 0.2678 (2) | 0.0504 (13) | |
N16 | 0.7638 (6) | −0.0743 (5) | 0.1827 (3) | 0.0792 (19) | |
O3 | 0.3252 (4) | 0.0539 (4) | 0.3587 (3) | 0.0792 (17) | |
O4 | 0.1491 (4) | 0.0458 (4) | 0.3452 (3) | 0.0895 (17) | |
C23 | 0.0680 (6) | −0.1309 (7) | 0.4448 (3) | 0.086 (3) | |
H23A | 0.0237 | −0.1366 | 0.4137 | 0.104* | |
C24 | 0.0229 (5) | −0.1187 (6) | 0.4971 (3) | 0.0627 (19) | |
C25 | 0.1865 (6) | −0.1075 (6) | 0.5344 (3) | 0.071 (2) | |
H25A | 0.2307 | −0.0969 | 0.5650 | 0.085* | |
C26 | 0.2328 (6) | −0.1237 (5) | 0.4826 (3) | 0.0562 (17) | |
C27 | 0.3500 (6) | −0.1277 (6) | 0.4758 (3) | 0.0569 (19) | |
C28 | 0.4188 (6) | −0.1227 (6) | 0.5214 (3) | 0.069 (2) | |
H28A | 0.3916 | −0.1190 | 0.5576 | 0.083* | |
C29 | 0.5277 (6) | −0.1233 (7) | 0.5126 (3) | 0.081 (3) | |
H29A | 0.5740 | −0.1185 | 0.5429 | 0.097* | |
C30 | 0.5669 (6) | −0.1308 (7) | 0.4603 (3) | 0.082 (3) | |
H30A | 0.6401 | −0.1321 | 0.4537 | 0.099* | |
C31 | 0.4952 (6) | −0.1365 (7) | 0.4169 (3) | 0.078 (3) | |
H31A | 0.5215 | −0.1420 | 0.3806 | 0.094* | |
C32 | −0.0910 (6) | −0.1207 (7) | 0.5061 (3) | 0.083 (3) | |
C33 | 0.3560 (5) | −0.1388 (4) | 0.2121 (2) | 0.0450 (15) | |
C34 | 0.4038 (6) | −0.1342 (9) | 0.1600 (4) | 0.105 (4) | |
H34A | 0.3618 | −0.1434 | 0.1284 | 0.126* | |
C35 | 0.5629 (5) | −0.1076 (5) | 0.1990 (3) | 0.0567 (17) | |
C36 | 0.5175 (5) | −0.1122 (5) | 0.2514 (3) | 0.0600 (18) | |
H36A | 0.5599 | −0.1032 | 0.2829 | 0.072* | |
C37 | 0.2388 (5) | −0.1545 (4) | 0.2175 (2) | 0.0451 (14) | |
C38 | 0.1781 (6) | −0.1766 (5) | 0.1720 (3) | 0.0629 (19) | |
H38A | 0.2100 | −0.1889 | 0.1377 | 0.075* | |
C39 | 0.0679 (7) | −0.1805 (6) | 0.1779 (3) | 0.076 (2) | |
H39A | 0.0254 | −0.1951 | 0.1472 | 0.091* | |
C40 | 0.0224 (6) | −0.1632 (6) | 0.2279 (3) | 0.072 (2) | |
H40A | −0.0514 | −0.1640 | 0.2322 | 0.087* | |
C41 | 0.0882 (5) | −0.1442 (5) | 0.2721 (3) | 0.0624 (19) | |
H41A | 0.0574 | −0.1337 | 0.3070 | 0.075* | |
C42 | 0.6758 (6) | −0.0875 (5) | 0.1905 (3) | 0.0636 (18) | |
C43 | 0.2342 (5) | 0.0832 (5) | 0.3523 (3) | 0.0583 (16) | |
C44 | 0.2298 (6) | 0.1823 (5) | 0.3488 (4) | 0.0670 (18) | |
F4 | 0.1610 (7) | 0.2222 (5) | 0.3759 (5) | 0.224 (6) | |
F5 | 0.2152 (12) | 0.2131 (5) | 0.3023 (3) | 0.271 (9) | |
F6 | 0.3113 (6) | 0.2237 (4) | 0.3644 (5) | 0.228 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0607 (3) | 0.0771 (3) | 0.0347 (2) | −0.0027 (2) | −0.0086 (2) | −0.0001 (2) |
N1 | 0.049 (3) | 0.063 (3) | 0.043 (3) | −0.001 (3) | 0.000 (2) | 0.002 (3) |
N2 | 0.062 (4) | 0.110 (5) | 0.056 (4) | −0.006 (4) | 0.013 (4) | −0.016 (4) |
N3 | 0.049 (3) | 0.072 (4) | 0.037 (3) | −0.007 (3) | −0.006 (2) | −0.002 (3) |
N4 | 0.072 (5) | 0.091 (5) | 0.115 (6) | −0.010 (4) | 0.031 (4) | −0.019 (4) |
N5 | 0.050 (4) | 0.153 (7) | 0.035 (3) | −0.003 (4) | −0.003 (3) | 0.000 (4) |
N6 | 0.058 (4) | 0.145 (7) | 0.052 (4) | 0.006 (4) | 0.003 (3) | 0.014 (4) |
N7 | 0.051 (3) | 0.094 (5) | 0.036 (3) | −0.006 (3) | 0.000 (2) | 0.010 (3) |
N8 | 0.047 (4) | 0.177 (9) | 0.103 (6) | −0.003 (5) | 0.007 (4) | −0.001 (6) |
O1 | 0.047 (3) | 0.068 (3) | 0.083 (3) | −0.001 (2) | −0.003 (3) | −0.002 (3) |
O2 | 0.049 (3) | 0.077 (3) | 0.097 (4) | 0.011 (2) | −0.007 (3) | −0.002 (4) |
C1 | 0.051 (4) | 0.070 (4) | 0.044 (4) | −0.007 (4) | 0.003 (3) | −0.006 (3) |
C2 | 0.048 (4) | 0.065 (4) | 0.055 (4) | 0.001 (3) | 0.007 (3) | 0.002 (3) |
C3 | 0.071 (5) | 0.106 (6) | 0.040 (4) | −0.003 (4) | 0.006 (4) | −0.014 (4) |
C4 | 0.059 (4) | 0.051 (4) | 0.041 (3) | −0.002 (4) | 0.007 (3) | 0.000 (3) |
C5 | 0.055 (4) | 0.063 (4) | 0.035 (3) | −0.011 (3) | −0.002 (3) | −0.001 (3) |
C6 | 0.078 (6) | 0.101 (6) | 0.044 (4) | −0.026 (5) | −0.009 (4) | −0.005 (4) |
C7 | 0.057 (5) | 0.151 (9) | 0.057 (5) | −0.030 (5) | −0.023 (4) | 0.016 (5) |
C8 | 0.056 (5) | 0.116 (7) | 0.068 (5) | −0.011 (5) | −0.018 (4) | 0.001 (5) |
C9 | 0.050 (4) | 0.101 (6) | 0.056 (4) | −0.016 (4) | 0.003 (3) | 0.004 (4) |
C10 | 0.058 (5) | 0.080 (5) | 0.067 (5) | −0.005 (4) | 0.016 (4) | −0.012 (4) |
C11 | 0.050 (4) | 0.076 (5) | 0.042 (3) | −0.004 (4) | −0.006 (3) | 0.013 (3) |
C12 | 0.056 (5) | 0.143 (8) | 0.045 (4) | 0.006 (5) | −0.005 (3) | 0.017 (5) |
C13 | 0.048 (4) | 0.097 (6) | 0.056 (5) | −0.008 (4) | −0.005 (3) | 0.013 (4) |
C14 | 0.051 (4) | 0.157 (9) | 0.049 (4) | −0.003 (5) | −0.011 (4) | 0.004 (5) |
C15 | 0.053 (4) | 0.059 (4) | 0.040 (3) | −0.004 (4) | −0.003 (3) | 0.004 (3) |
C16 | 0.071 (5) | 0.144 (9) | 0.037 (4) | −0.009 (5) | −0.002 (3) | 0.014 (5) |
C17 | 0.052 (4) | 0.155 (10) | 0.045 (4) | −0.005 (5) | −0.013 (3) | 0.016 (5) |
C18 | 0.051 (4) | 0.115 (7) | 0.056 (4) | 0.001 (4) | −0.007 (3) | 0.002 (5) |
C19 | 0.051 (4) | 0.128 (7) | 0.045 (4) | 0.009 (5) | −0.004 (3) | 0.013 (5) |
C20 | 0.055 (5) | 0.119 (7) | 0.063 (5) | 0.004 (5) | 0.000 (4) | 0.010 (5) |
C21 | 0.039 (3) | 0.070 (4) | 0.047 (3) | 0.008 (3) | 0.001 (3) | −0.004 (4) |
C22 | 0.044 (4) | 0.070 (4) | 0.075 (5) | 0.005 (3) | 0.011 (4) | 0.008 (4) |
F1 | 0.145 (6) | 0.068 (4) | 0.50 (2) | −0.009 (4) | −0.149 (10) | −0.026 (7) |
F2 | 0.54 (3) | 0.081 (4) | 0.147 (7) | 0.007 (9) | −0.076 (12) | 0.029 (4) |
F3 | 0.208 (9) | 0.073 (4) | 0.390 (15) | 0.004 (5) | 0.164 (10) | −0.035 (6) |
Ag2 | 0.0630 (3) | 0.0748 (3) | 0.0334 (2) | 0.0014 (2) | −0.0081 (2) | −0.0026 (2) |
N9 | 0.052 (4) | 0.127 (6) | 0.042 (3) | −0.008 (4) | −0.005 (3) | 0.003 (3) |
N10 | 0.059 (4) | 0.124 (6) | 0.043 (3) | 0.013 (4) | 0.010 (3) | 0.008 (4) |
N11 | 0.049 (3) | 0.107 (5) | 0.034 (3) | 0.005 (3) | −0.003 (2) | 0.009 (3) |
N12 | 0.057 (5) | 0.216 (11) | 0.098 (6) | −0.009 (6) | −0.009 (4) | 0.005 (7) |
N13 | 0.045 (3) | 0.079 (4) | 0.042 (3) | −0.009 (3) | −0.003 (2) | −0.005 (3) |
N14 | 0.049 (3) | 0.219 (9) | 0.046 (3) | −0.011 (5) | 0.008 (3) | 0.002 (6) |
N15 | 0.040 (3) | 0.073 (4) | 0.038 (3) | −0.001 (3) | −0.005 (2) | −0.005 (2) |
N16 | 0.055 (4) | 0.086 (5) | 0.096 (5) | −0.012 (4) | 0.012 (4) | −0.010 (4) |
O3 | 0.067 (3) | 0.066 (3) | 0.104 (5) | 0.003 (3) | −0.018 (3) | −0.007 (3) |
O4 | 0.059 (3) | 0.100 (4) | 0.110 (5) | −0.016 (3) | 0.000 (4) | −0.022 (4) |
C23 | 0.047 (4) | 0.160 (10) | 0.051 (5) | −0.011 (5) | −0.011 (4) | −0.004 (5) |
C24 | 0.048 (4) | 0.087 (5) | 0.053 (4) | 0.006 (4) | 0.009 (3) | 0.011 (4) |
C25 | 0.055 (4) | 0.117 (6) | 0.040 (4) | 0.005 (4) | 0.001 (3) | −0.006 (4) |
C26 | 0.059 (4) | 0.066 (4) | 0.044 (3) | −0.001 (4) | −0.010 (3) | 0.009 (3) |
C27 | 0.056 (4) | 0.080 (5) | 0.035 (4) | −0.002 (4) | −0.003 (3) | 0.004 (3) |
C28 | 0.060 (4) | 0.108 (7) | 0.040 (4) | −0.001 (4) | −0.007 (3) | 0.009 (4) |
C29 | 0.054 (4) | 0.140 (9) | 0.049 (4) | −0.003 (5) | −0.012 (4) | −0.001 (5) |
C30 | 0.050 (4) | 0.140 (8) | 0.057 (5) | −0.001 (5) | −0.001 (4) | 0.012 (5) |
C31 | 0.058 (5) | 0.132 (8) | 0.045 (4) | 0.002 (5) | 0.007 (3) | 0.004 (4) |
C32 | 0.055 (5) | 0.129 (8) | 0.064 (5) | 0.006 (5) | 0.006 (4) | 0.006 (5) |
C33 | 0.043 (3) | 0.058 (4) | 0.034 (3) | 0.003 (3) | −0.004 (3) | −0.003 (3) |
C34 | 0.053 (4) | 0.218 (12) | 0.045 (4) | −0.008 (6) | −0.003 (4) | −0.016 (7) |
C35 | 0.043 (3) | 0.070 (4) | 0.058 (4) | 0.006 (3) | 0.002 (3) | 0.001 (4) |
C36 | 0.054 (4) | 0.080 (5) | 0.046 (4) | −0.007 (4) | −0.005 (3) | −0.008 (4) |
C37 | 0.045 (3) | 0.056 (3) | 0.034 (3) | 0.001 (3) | −0.003 (3) | −0.004 (2) |
C38 | 0.060 (4) | 0.090 (5) | 0.039 (4) | −0.013 (4) | −0.005 (3) | −0.001 (3) |
C39 | 0.068 (5) | 0.101 (6) | 0.057 (5) | −0.026 (5) | −0.017 (4) | 0.002 (4) |
C40 | 0.045 (4) | 0.098 (6) | 0.074 (6) | −0.012 (4) | −0.017 (4) | 0.009 (5) |
C41 | 0.043 (4) | 0.090 (6) | 0.054 (4) | 0.003 (4) | 0.002 (3) | −0.003 (4) |
C42 | 0.056 (4) | 0.074 (5) | 0.061 (4) | 0.001 (4) | 0.009 (3) | −0.009 (4) |
C43 | 0.050 (4) | 0.075 (4) | 0.050 (4) | 0.005 (3) | −0.005 (3) | −0.003 (3) |
C44 | 0.050 (4) | 0.076 (5) | 0.075 (5) | 0.008 (4) | −0.002 (5) | 0.002 (5) |
F4 | 0.208 (9) | 0.101 (5) | 0.363 (14) | 0.032 (5) | 0.175 (10) | −0.015 (6) |
F5 | 0.58 (3) | 0.102 (5) | 0.135 (7) | 0.060 (11) | −0.064 (12) | 0.023 (5) |
F6 | 0.152 (7) | 0.067 (4) | 0.464 (18) | 0.001 (4) | −0.135 (10) | −0.016 (7) |
Ag1—N7 | 2.272 (5) | Ag2—N15 | 2.254 (5) |
Ag1—N3 | 2.295 (5) | Ag2—N11 | 2.290 (5) |
Ag1—O1 | 2.425 (5) | Ag2—O3 | 2.481 (5) |
Ag1—N1 | 2.552 (5) | N9—C23 | 1.315 (10) |
N1—C4 | 1.317 (8) | N9—C26 | 1.317 (9) |
N1—C1 | 1.337 (8) | N10—C24 | 1.307 (9) |
N2—C3 | 1.322 (10) | N10—C25 | 1.338 (9) |
N2—C2 | 1.349 (9) | N11—C27 | 1.330 (8) |
N3—C9 | 1.317 (9) | N11—C31 | 1.338 (9) |
N3—C5 | 1.342 (8) | N12—C32 | 1.133 (10) |
N4—C10 | 1.138 (9) | N13—C36 | 1.322 (8) |
N5—C11 | 1.323 (9) | N13—C33 | 1.322 (8) |
N5—C14 | 1.335 (9) | N14—C35 | 1.316 (9) |
N6—C12 | 1.310 (9) | N14—C34 | 1.320 (10) |
N6—C13 | 1.331 (9) | N15—C41 | 1.335 (8) |
N7—C19 | 1.298 (9) | N15—C37 | 1.340 (7) |
N7—C15 | 1.340 (8) | N16—C42 | 1.135 (9) |
N8—C20 | 1.125 (9) | O3—C43 | 1.231 (8) |
O1—C21 | 1.236 (7) | O4—C43 | 1.217 (8) |
O2—C21 | 1.228 (7) | C23—C24 | 1.380 (10) |
C1—C2 | 1.383 (9) | C23—H23A | 0.9300 |
C1—H1A | 0.9300 | C24—C32 | 1.443 (10) |
C2—C10 | 1.443 (10) | C25—C26 | 1.386 (9) |
C3—C4 | 1.390 (9) | C25—H25A | 0.9300 |
C3—H3A | 0.9300 | C26—C27 | 1.478 (10) |
C4—C5 | 1.505 (10) | C27—C28 | 1.389 (9) |
C5—C6 | 1.373 (9) | C28—C29 | 1.379 (10) |
C6—C7 | 1.368 (12) | C28—H28A | 0.9300 |
C6—H6A | 0.9300 | C29—C30 | 1.346 (10) |
C7—C8 | 1.348 (11) | C29—H29A | 0.9300 |
C7—H7A | 0.9300 | C30—C31 | 1.374 (10) |
C8—C9 | 1.378 (10) | C30—H30A | 0.9300 |
C8—H8A | 0.9300 | C31—H31A | 0.9300 |
C9—H9A | 0.9300 | C33—C34 | 1.382 (10) |
C11—C12 | 1.381 (10) | C33—C37 | 1.492 (9) |
C11—C15 | 1.487 (9) | C34—H34A | 0.9300 |
C12—H12A | 0.9300 | C35—C36 | 1.374 (9) |
C13—C14 | 1.366 (10) | C35—C42 | 1.460 (10) |
C13—C20 | 1.451 (10) | C36—H36A | 0.9300 |
C14—H14A | 0.9300 | C37—C38 | 1.366 (8) |
C15—C16 | 1.391 (10) | C38—C39 | 1.388 (11) |
C16—C17 | 1.370 (11) | C38—H38A | 0.9300 |
C16—H16A | 0.9300 | C39—C40 | 1.347 (11) |
C17—C18 | 1.353 (10) | C39—H39A | 0.9300 |
C17—H17A | 0.9300 | C40—C41 | 1.368 (10) |
C18—C19 | 1.375 (10) | C40—H40A | 0.9300 |
C18—H18A | 0.9300 | C41—H41A | 0.9300 |
C19—H19A | 0.9300 | C43—C44 | 1.486 (10) |
C21—C22 | 1.467 (10) | C44—F5 | 1.215 (9) |
C22—F3 | 1.218 (8) | C44—F4 | 1.231 (9) |
C22—F2 | 1.243 (9) | C44—F6 | 1.251 (9) |
C22—F1 | 1.245 (8) | ||
N7—Ag1—N3 | 154.8 (2) | F2—C22—C21 | 113.1 (8) |
N7—Ag1—O1 | 106.2 (2) | F1—C22—C21 | 117.6 (6) |
N3—Ag1—O1 | 98.7 (2) | N15—Ag2—N11 | 157.2 (2) |
N7—Ag1—N1 | 111.66 (17) | N15—Ag2—O3 | 114.1 (2) |
N3—Ag1—N1 | 68.41 (17) | N11—Ag2—O3 | 88.1 (2) |
O1—Ag1—N1 | 97.50 (19) | C23—N9—C26 | 117.9 (7) |
C4—N1—C1 | 118.1 (6) | C24—N10—C25 | 115.8 (6) |
C4—N1—Ag1 | 113.5 (4) | C27—N11—C31 | 119.2 (6) |
C1—N1—Ag1 | 128.5 (4) | C27—N11—Ag2 | 122.0 (5) |
C3—N2—C2 | 115.1 (6) | C31—N11—Ag2 | 117.1 (4) |
C9—N3—C5 | 117.3 (6) | C36—N13—C33 | 117.9 (6) |
C9—N3—Ag1 | 118.7 (5) | C35—N14—C34 | 115.9 (7) |
C5—N3—Ag1 | 122.6 (4) | C41—N15—C37 | 118.3 (6) |
C11—N5—C14 | 117.8 (6) | C41—N15—Ag2 | 117.2 (4) |
C12—N6—C13 | 115.7 (7) | C37—N15—Ag2 | 124.5 (4) |
C19—N7—C15 | 118.0 (6) | C43—O3—Ag2 | 98.8 (4) |
C19—N7—Ag1 | 116.3 (4) | N9—C23—C24 | 121.5 (7) |
C15—N7—Ag1 | 125.1 (5) | N9—C23—H23A | 119.3 |
C21—O1—Ag1 | 105.4 (4) | C24—C23—H23A | 119.3 |
N1—C1—C2 | 120.9 (6) | N10—C24—C23 | 122.2 (6) |
N1—C1—H1A | 119.5 | N10—C24—C32 | 115.3 (6) |
C2—C1—H1A | 119.5 | C23—C24—C32 | 122.4 (7) |
N2—C2—C1 | 122.0 (6) | N10—C25—C26 | 122.6 (6) |
N2—C2—C10 | 115.6 (6) | N10—C25—H25A | 118.7 |
C1—C2—C10 | 122.4 (7) | C26—C25—H25A | 118.7 |
N2—C3—C4 | 123.7 (7) | N9—C26—C25 | 119.9 (7) |
N2—C3—H3A | 118.1 | N9—C26—C27 | 118.7 (6) |
C4—C3—H3A | 118.1 | C25—C26—C27 | 121.4 (6) |
N1—C4—C3 | 120.1 (7) | N11—C27—C28 | 120.0 (7) |
N1—C4—C5 | 118.2 (6) | N11—C27—C26 | 118.2 (6) |
C3—C4—C5 | 121.1 (6) | C28—C27—C26 | 121.8 (6) |
N3—C5—C6 | 122.1 (7) | C29—C28—C27 | 119.6 (7) |
N3—C5—C4 | 116.2 (6) | C29—C28—H28A | 120.2 |
C6—C5—C4 | 121.7 (6) | C27—C28—H28A | 120.2 |
C5—C6—C7 | 119.3 (8) | C30—C29—C28 | 120.1 (7) |
C5—C6—H6A | 120.4 | C30—C29—H29A | 119.9 |
C7—C6—H6A | 120.4 | C28—C29—H29A | 119.9 |
C8—C7—C6 | 118.9 (7) | C29—C30—C31 | 117.7 (7) |
C8—C7—H7A | 120.6 | C29—C30—H30A | 121.1 |
C6—C7—H7A | 120.6 | C31—C30—H30A | 121.1 |
C7—C8—C9 | 119.0 (8) | N11—C31—C30 | 123.3 (7) |
C7—C8—H8A | 120.5 | N11—C31—H31A | 118.3 |
C9—C8—H8A | 120.5 | C30—C31—H31A | 118.3 |
N3—C9—C8 | 123.3 (7) | N12—C32—C24 | 176.9 (10) |
N3—C9—H9A | 118.3 | N13—C33—C34 | 119.7 (6) |
C8—C9—H9A | 118.3 | N13—C33—C37 | 119.5 (5) |
N4—C10—C2 | 177.1 (9) | C34—C33—C37 | 120.8 (6) |
N5—C11—C12 | 118.5 (6) | N14—C34—C33 | 123.2 (8) |
N5—C11—C15 | 119.6 (6) | N14—C34—H34A | 118.4 |
C12—C11—C15 | 121.9 (6) | C33—C34—H34A | 118.4 |
N6—C12—C11 | 124.8 (7) | N14—C35—C36 | 122.2 (6) |
N6—C12—H12A | 117.6 | N14—C35—C42 | 115.3 (6) |
C11—C12—H12A | 117.6 | C36—C35—C42 | 122.5 (6) |
N6—C13—C14 | 121.0 (7) | N13—C36—C35 | 121.1 (6) |
N6—C13—C20 | 115.9 (7) | N13—C36—H36A | 119.4 |
C14—C13—C20 | 123.1 (7) | C35—C36—H36A | 119.4 |
N5—C14—C13 | 122.0 (7) | N15—C37—C38 | 121.2 (6) |
N5—C14—H14A | 119.0 | N15—C37—C33 | 117.4 (5) |
C13—C14—H14A | 119.0 | C38—C37—C33 | 121.2 (6) |
N7—C15—C16 | 121.3 (7) | C37—C38—C39 | 119.0 (7) |
N7—C15—C11 | 117.4 (6) | C37—C38—H38A | 120.5 |
C16—C15—C11 | 121.3 (6) | C39—C38—H38A | 120.5 |
C17—C16—C15 | 118.5 (7) | C40—C39—C38 | 120.1 (7) |
C17—C16—H16A | 120.7 | C40—C39—H39A | 120.0 |
C15—C16—H16A | 120.7 | C38—C39—H39A | 120.0 |
C18—C17—C16 | 119.9 (7) | C39—C40—C41 | 117.9 (7) |
C18—C17—H17A | 120.1 | C39—C40—H40A | 121.1 |
C16—C17—H17A | 120.1 | C41—C40—H40A | 121.1 |
C17—C18—C19 | 117.6 (7) | N15—C41—C40 | 123.4 (7) |
C17—C18—H18A | 121.2 | N15—C41—H41A | 118.3 |
C19—C18—H18A | 121.2 | C40—C41—H41A | 118.3 |
N7—C19—C18 | 124.6 (7) | N16—C42—C35 | 177.6 (9) |
N7—C19—H19A | 117.7 | O4—C43—O3 | 131.6 (7) |
C18—C19—H19A | 117.7 | O4—C43—C44 | 114.8 (6) |
N8—C20—C13 | 177.4 (9) | O3—C43—C44 | 113.4 (6) |
O2—C21—O1 | 129.9 (7) | F5—C44—F4 | 101.0 (8) |
O2—C21—C22 | 116.2 (6) | F5—C44—F6 | 101.9 (9) |
O1—C21—C22 | 113.8 (5) | F4—C44—F6 | 100.1 (8) |
F3—C22—F2 | 99.2 (8) | F5—C44—C43 | 115.7 (8) |
F3—C22—F1 | 104.2 (9) | F4—C44—C43 | 118.8 (8) |
F2—C22—F1 | 98.4 (8) | F6—C44—C43 | 116.5 (7) |
F3—C22—C21 | 120.5 (7) | ||
N7—Ag1—N1—C4 | −149.5 (5) | Ag1—O1—C21—C22 | 178.3 (5) |
N3—Ag1—N1—C4 | 3.3 (5) | O2—C21—C22—F3 | 142.7 (10) |
O1—Ag1—N1—C4 | 99.7 (5) | O1—C21—C22—F3 | −38.0 (13) |
N7—Ag1—N1—C1 | 31.1 (6) | O2—C21—C22—F2 | −100.3 (11) |
N3—Ag1—N1—C1 | −176.0 (7) | O1—C21—C22—F2 | 79.0 (11) |
O1—Ag1—N1—C1 | −79.7 (6) | O2—C21—C22—F1 | 13.5 (13) |
N7—Ag1—N3—C9 | −94.7 (7) | O1—C21—C22—F1 | −167.2 (10) |
O1—Ag1—N3—C9 | 75.4 (6) | N15—Ag2—N11—C27 | −109.2 (7) |
N1—Ag1—N3—C9 | 170.1 (7) | O3—Ag2—N11—C27 | 83.7 (7) |
N7—Ag1—N3—C5 | 98.8 (7) | N15—Ag2—N11—C31 | 86.1 (9) |
O1—Ag1—N3—C5 | −91.1 (6) | O3—Ag2—N11—C31 | −81.0 (7) |
N1—Ag1—N3—C5 | 3.6 (5) | N11—Ag2—N15—C41 | 101.2 (7) |
N3—Ag1—N7—C19 | −100.3 (8) | O3—Ag2—N15—C41 | −93.0 (6) |
O1—Ag1—N7—C19 | 90.0 (7) | N11—Ag2—N15—C37 | −79.6 (7) |
N1—Ag1—N7—C19 | −15.2 (7) | O3—Ag2—N15—C37 | 86.2 (5) |
N3—Ag1—N7—C15 | 89.0 (8) | N15—Ag2—O3—C43 | 51.4 (6) |
O1—Ag1—N7—C15 | −80.8 (6) | N11—Ag2—O3—C43 | −134.1 (5) |
N1—Ag1—N7—C15 | 174.1 (6) | C26—N9—C23—C24 | −2.0 (15) |
N7—Ag1—O1—C21 | −53.2 (5) | C25—N10—C24—C23 | −0.6 (14) |
N3—Ag1—O1—C21 | 131.2 (5) | C25—N10—C24—C32 | 177.8 (9) |
N1—Ag1—O1—C21 | 62.0 (5) | N9—C23—C24—N10 | 2.9 (16) |
C4—N1—C1—C2 | −1.2 (11) | N9—C23—C24—C32 | −175.4 (10) |
Ag1—N1—C1—C2 | 178.1 (5) | C24—N10—C25—C26 | −2.4 (13) |
C3—N2—C2—C1 | −4.0 (12) | C23—N9—C26—C25 | −0.9 (13) |
C3—N2—C2—C10 | 176.3 (8) | C23—N9—C26—C27 | −180.0 (9) |
N1—C1—C2—N2 | 4.1 (12) | N10—C25—C26—N9 | 3.3 (13) |
N1—C1—C2—C10 | −176.2 (7) | N10—C25—C26—C27 | −177.7 (8) |
C2—N2—C3—C4 | 1.4 (13) | C31—N11—C27—C28 | 0.2 (13) |
C1—N1—C4—C3 | −1.4 (11) | Ag2—N11—C27—C28 | −164.2 (6) |
Ag1—N1—C4—C3 | 179.2 (6) | C31—N11—C27—C26 | 178.8 (8) |
C1—N1—C4—C5 | 170.4 (6) | Ag2—N11—C27—C26 | 14.4 (11) |
Ag1—N1—C4—C5 | −9.1 (8) | N9—C26—C27—N11 | 5.8 (13) |
N2—C3—C4—N1 | 1.4 (13) | C25—C26—C27—N11 | −173.2 (8) |
N2—C3—C4—C5 | −170.1 (8) | N9—C26—C27—C28 | −175.6 (8) |
C9—N3—C5—C6 | 2.5 (11) | C25—C26—C27—C28 | 5.3 (13) |
Ag1—N3—C5—C6 | 169.2 (6) | N11—C27—C28—C29 | 1.0 (14) |
C9—N3—C5—C4 | −176.1 (7) | C26—C27—C28—C29 | −177.5 (9) |
Ag1—N3—C5—C4 | −9.4 (9) | C27—C28—C29—C30 | −1.6 (16) |
N1—C4—C5—N3 | 12.4 (10) | C28—C29—C30—C31 | 0.9 (16) |
C3—C4—C5—N3 | −175.9 (7) | C27—N11—C31—C30 | −0.9 (15) |
N1—C4—C5—C6 | −166.2 (7) | Ag2—N11—C31—C30 | 164.2 (8) |
C3—C4—C5—C6 | 5.4 (12) | C29—C30—C31—N11 | 0.4 (16) |
N3—C5—C6—C7 | −4.0 (13) | C36—N13—C33—C34 | 2.6 (12) |
C4—C5—C6—C7 | 174.6 (8) | C36—N13—C33—C37 | −177.5 (7) |
C5—C6—C7—C8 | 1.6 (15) | C35—N14—C34—C33 | 2.2 (17) |
C6—C7—C8—C9 | 1.9 (15) | N13—C33—C34—N14 | −2.7 (17) |
C5—N3—C9—C8 | 1.2 (13) | C37—C33—C34—N14 | 177.5 (10) |
Ag1—N3—C9—C8 | −166.0 (7) | C34—N14—C35—C36 | −1.9 (15) |
C7—C8—C9—N3 | −3.4 (15) | C34—N14—C35—C42 | −179.0 (9) |
C14—N5—C11—C12 | 0.3 (14) | C33—N13—C36—C35 | −2.4 (11) |
C14—N5—C11—C15 | 179.1 (9) | N14—C35—C36—N13 | 2.1 (13) |
C13—N6—C12—C11 | −0.5 (15) | C42—C35—C36—N13 | 179.0 (7) |
N5—C11—C12—N6 | −1.0 (15) | C41—N15—C37—C38 | −2.8 (10) |
C15—C11—C12—N6 | −179.9 (9) | Ag2—N15—C37—C38 | 178.0 (5) |
C12—N6—C13—C14 | 2.8 (15) | C41—N15—C37—C33 | 172.7 (6) |
C12—N6—C13—C20 | −178.0 (9) | Ag2—N15—C37—C33 | −6.4 (8) |
C11—N5—C14—C13 | 2.0 (16) | N13—C33—C37—N15 | 13.5 (10) |
N6—C13—C14—N5 | −3.7 (17) | C34—C33—C37—N15 | −166.7 (8) |
C20—C13—C14—N5 | 177.1 (10) | N13—C33—C37—C38 | −170.9 (7) |
C19—N7—C15—C16 | 1.8 (12) | C34—C33—C37—C38 | 8.9 (12) |
Ag1—N7—C15—C16 | 172.4 (7) | N15—C37—C38—C39 | 2.7 (11) |
C19—N7—C15—C11 | −178.0 (8) | C33—C37—C38—C39 | −172.7 (7) |
Ag1—N7—C15—C11 | −7.4 (10) | C37—C38—C39—C40 | −0.4 (13) |
N5—C11—C15—N7 | −6.9 (13) | C38—C39—C40—C41 | −1.6 (14) |
C12—C11—C15—N7 | 171.9 (8) | C37—N15—C41—C40 | 0.6 (12) |
N5—C11—C15—C16 | 173.4 (9) | Ag2—N15—C41—C40 | 179.9 (6) |
C12—C11—C15—C16 | −7.8 (13) | C39—C40—C41—N15 | 1.6 (13) |
N7—C15—C16—C17 | −2.2 (14) | Ag2—O3—C43—O4 | 3.7 (11) |
C11—C15—C16—C17 | 177.6 (9) | Ag2—O3—C43—C44 | −171.6 (6) |
C15—C16—C17—C18 | 1.2 (16) | O4—C43—C44—F5 | −71.1 (12) |
C16—C17—C18—C19 | 0.0 (16) | O3—C43—C44—F5 | 105.0 (11) |
C15—N7—C19—C18 | −0.5 (15) | O4—C43—C44—F4 | 49.4 (13) |
Ag1—N7—C19—C18 | −171.9 (8) | O3—C43—C44—F4 | −134.5 (10) |
C17—C18—C19—N7 | −0.4 (16) | O4—C43—C44—F6 | 169.2 (9) |
Ag1—O1—C21—O2 | −2.5 (10) | O3—C43—C44—F6 | −14.7 (13) |
Experimental details
Crystal data | |
Chemical formula | [Ag(C10H6N4)2(C2F3O2)] |
Mr | 585.27 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 12.5237 (16), 14.9638 (18), 23.845 (3) |
V (Å3) | 4468.6 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.97 |
Crystal size (mm) | 0.41 × 0.31 × 0.29 |
Data collection | |
Diffractometer | Bruker APEXII CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.861, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24472, 7881, 6180 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.129, 1.02 |
No. of reflections | 7881 |
No. of parameters | 649 |
No. of restraints | 10 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −0.64 |
Absolute structure | Flack (1983), 3488 Friedel pairs |
Absolute structure parameter | −0.10 (4) |
Computer programs: APEX2 (Bruker 2007), APEX2 and SAINT (Bruker 2007), SAINT (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
The authors are grateful for financial support from the Science and Technology Program, Tianjin Municipal Commission.
References
Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
Choudhury, A. R., Urs, U. K., Nagarajan, K. & Row, T. N. G. (2002). J. Mol. Struct. 605, 71–75. Web of Science CSD CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
O'Keeffe, M. & Yaghi, O. M. (2012). Chem. Rev. 112, 675–702. Web of Science CAS PubMed Google Scholar
Pauling, L. (1960). The Nature of the Chemical Bond, p. 260. New York: Cornell University Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z.-J., Zhang, F. & Wan, C.-Q. (2010). Acta Cryst. E66, m1232–m1233. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y., Zhao, X.-Q., Shi, W., Cheng, P., Liao, D.-Z. & Yan, S.-P. (2009). Cryst. Growth Des. 9, 2137–2145. Web of Science CSD CrossRef CAS Google Scholar
Zhang, F. & Yang, Y.-L. (2011). Acta Cryst. E67, m1863. Web of Science CSD CrossRef 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.
Multidentate ligands are widely used to construct diverse metal-organic frameworks with attractive topological structures and interesting properties (Wang et al., 2009; O'Keeffe & Yaghi, 2012). 5-(2-pyridyl)pyrazine-2-carbonitrile is a new member of the family of pyridyl-based multidentate ligands, several mononuclear silver(I) complexes of which were reported recently (Wang et al., 2010; Zhang & Yang, 2011). In the present context, we report the structure of a AgI complex with 5-(2-pyridyl)pyrazine-2-carbonitrile, the title compound [Ag(C10H6N4)2 (CF3CO2)] (Scheme 1).
As shown in Fig. 1, there are two independent but slightly different mononuclear units (associated with Ag1 and Ag2) in the asymmetric unit of the title complex. For Ag1, a pair of chelating κ2N,N 5-(2-pyridyl)pyrazine-2-carbonitrile ligands surround the Ag center to form a N4O-pyramidal coordination geometry, with a trifluoroacetate O bonding at the vertex site. The four N donors exibit different Ag—N bond lengths, with the Ag1—N5 [2.706 (4) Å] longer than the others [2.272 (5)–2.552 (5)Å]. The Ag2 unit exhibits a similar N4O-geometry to that for Ag1. However, both Ag2—N9 [2.647 (5) Å] and Ag2—N13 [2.675 (5) Å] are both longer than the other two Ag—N bonds [2.254 (5)–2.290 (5)Å]. This N4O-pyramidal coordination geometry is comparable to that found in the previously reported Ag complex with 5-(2-pyridyl)pyrazine-2-carbonitrile [Ag(C10H6N4)2]NO3 (Zhang & Yang, 2011). Interestingly, the two mononuclear units in the title complex are interconnected by a short F2···F5 interaction [2.586 (4) Å], giving a dimer. This F···F separation is much shorter than the sum of the van der Waals radii (2.70 Å) (Pauling, 1960), and the distance found in 1-(4-fluorophenyl)-2-phenyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline [2.778 (2) %A] (Choudhury et al., 2002).
In the present complex, F···F-connected dimers are interconnected through weak π···π stacking interactions between adjacent pyridyl rings and pyrazinyl rings, forming columns along b (Fig.2). The minimum distance between Cg1 (N1—C1—C2—N2—C3—C4) and Cg2i (C37—C38—C39—C40—C41—N15) is 3.836 (5) Å, while that between Cg3 (C5—C6—C7—C8—C9—N3) and Cg4i (N13—C33—C34 —N14—C35—C36) is 3.975 (3) Å [symmetry code: (i) x, y + 1, z]. Present within the columns are found short nonbonding N···C contacts between the acetonitrile N atoms and pyrazinyl C atoms (Fig. 3). These are N4···C37ii [3.246 (5) Å] and N16···C4iii [3.148 (4) Å] [symmetry codes: (ii) -x, y + 1/2, -z + 1/2; (iii) -x + 1, y - 1/2, -z + 1/2].