metal-organic compounds
catena-Poly[[silver(I)-μ-N-(pyridin-3-ylmethyl)pyridine-2-amine-κ2N:N′] trifluoromethanesulfonate]
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: kmpark@gnu.ac.kr
In the 11H11N3)](CF3SO3)}n, there are two AgI atoms, two N-(pyridin-3-ylmethyl)pyridine-2-amine ligands (A and B) and two CF3SO3− anions. One AgI atom is coordinated by two pyridine N atoms from two symmetry-related A ligands in a geometry slightly distorted from linear [N—Ag—N = 173.2 (3)°], forming a left-handed helical chain, while the other AgI atom is coordinated by two pyridine N atoms from two symmetry-related B ligands in a bent arrangement [N—Ag—N = 157.1 (3)°], forming a right-handed helical chain. Both helical chains have the same pitch length [10.4007 (7) Å], propagate along the b-axis direction and are alternately arranged via Ag⋯Ag [3.0897 (12) Å] and π–π stacking interactions [centroid–centroid distances = 3.564 (7) and 3.518 (6) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane. Intermolecular N—H⋯O, C—H⋯O and C—H⋯F hydrogen-bonding interactions occur between the helical chains and the anions.
of the title polymeric complex, {[Ag(CRelated literature
For related structures and applications of AgI coordination polymers with dipyridyl ligands, see: Leong & Vittal (2011); Moulton & Zaworotko (2001). For the of the related perchlorate salt, see: Zhang et al. (2013). For the synthesis of the ligand, see: Foxon et al. (2002); Lee et al. (2008).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
https://doi.org/10.1107/S1600536813016309/sj5332sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016309/sj5332Isup2.hkl
The ligand (N-(pyridin-3-ylmethyl)pyridine-2-amine) was prepared 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 a 1:1 molar ratio in methanol.
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).
Silver coordination polymers based on dipyridyl type ligands have attracted particular interest because of the intriguing architectures caused by a variety of coordination geometries for the Ag(I) cation as well as their potential applications as functional materials (Leong & Vittal, 2011; Moulton & Zaworotko, 2001). However, despite the rapid growth in the Ag(I) coordination chemistry based on symmetrical dipyridyl ligands, investigations using unsymmetrical dipyridyl ligands with nitrogen donor atoms in different positions on the two terminal pyridines still remains lacking. Herein, we report the
of the title compound prepared by the reaction of silver trifluoromethanesulfonate with the unsymmetrical dipyridyl ligand. The structure of title compound is isostructural with the perchlorate salt (Zhang et al., 2013).The π–π stacking interactions [centroid-centroid distances = 3.564 (7) and 3.518 (6) Å] between pyridine rings of both helical chains, as shown in Fig. 2, contribute to stabilize the two-dimensional network.
of the title compound contains two AgI atoms (Ag1 and Ag2), two N-(pyridin-3-ylmethyl)pyridine-2-amine (Foxon et al., 2002; Lee et al., 2008) ligands (A and B) and two CF3SO3- anions. The Ag1 atom is coordinated by two pyridine N atoms from two symmetry-related ligand A in a geometry slightly distorted from linear [N–Ag1–N = 173.2 (3)°] to form left-handed helical chain, while the Ag2 atom is coordinated by two pyridine N atoms from two symmetry-related ligand B in a bent arrangement [N–Ag2–N = 157.1 (3)°] to form right-handed helical chain (Fig. 1). Two pyridine rings coordinated to the Ag1 and Ag2 centers are tilted by 14.2 (7)° and 34.1 (5)°, respectively, with respect to each other. Both helical chains with the same pitch length of 10.4007 (7) Å propagate along the b axis and are alternately arranged via the Ag···Ag interactions [3.0897 (12) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane. Furthermore,The non-coordinating CF3SO3- anions participate in N–H···O hydrogen bonding (Table 1, Fig. 2) and Ag···O interactions (Ag1···O4 2.815 (8), Ag1···O5 2.852 (10), Ag1···O1 2.867 (8), Ag2···O2 2.722 (8) Å) (Fig. 1,2). In addition, C–H···O and C–H···F hydrogen bonds (Table 1) between the helical chains and anions are also detected in the crystal.
For related structures and applications of AgI coordination polymers with dipyridyl ligands, see: Leong & Vittal (2011); Moulton & Zaworotko (2001). For the
of the isotypic perchlorate salt, see: Zhang et al. (2013). For the synthesis of the ligand, see: Foxon et al. (2002); Lee et al. (2008).Data collection: SMART (Bruker, 2000); cell
SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. A view of the molecular structure of the title compound, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level and dashed lines present Ag···O and N–H···O contacts. [Symmetry codes: (i) 1 - x, 1/2 + y, 1/2 - z; (ii) -x, 1/2 + y, 1/2 - z; (iii) 1 - x, -1/2 + y, 1/2 - z; (iv) -x, -1/2 + y, 1/2 - z]. | |
Fig. 2. The two-dimensional supramolecular structure formed through Ag···Ag and Ag···O interactions (yellow dashed lines) and π–π stacking interactions (black dashed lines). Red dashed lines present N–H···O hydrogen bonds. |
[Ag(C11H11N3)](CF3O3S) | F(000) = 1744 |
Mr = 442.17 | Dx = 1.990 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5912 reflections |
a = 14.0965 (10) Å | θ = 2.2–28.1° |
b = 10.4007 (7) Å | µ = 1.56 mm−1 |
c = 20.6593 (15) Å | T = 173 K |
β = 102.994 (1)° | Block, colourless |
V = 2951.4 (4) Å3 | 0.30 × 0.25 × 0.25 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 5797 independent reflections |
Radiation source: fine-focus sealed tube | 4479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −17→14 |
Tmin = 0.652, Tmax = 0.697 | k = −12→12 |
16169 measured reflections | l = −15→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.238 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1255P)2 + 38.027P] where P = (Fo2 + 2Fc2)/3 |
5797 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 2.70 e Å−3 |
6 restraints | Δρmin = −1.89 e Å−3 |
[Ag(C11H11N3)](CF3O3S) | V = 2951.4 (4) Å3 |
Mr = 442.17 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.0965 (10) Å | µ = 1.56 mm−1 |
b = 10.4007 (7) Å | T = 173 K |
c = 20.6593 (15) Å | 0.30 × 0.25 × 0.25 mm |
β = 102.994 (1)° |
Bruker SMART CCD area-detector diffractometer | 5797 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4479 reflections with I > 2σ(I) |
Tmin = 0.652, Tmax = 0.697 | Rint = 0.047 |
16169 measured reflections |
R[F2 > 2σ(F2)] = 0.088 | 6 restraints |
wR(F2) = 0.238 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1255P)2 + 38.027P] where P = (Fo2 + 2Fc2)/3 |
5797 reflections | Δρmax = 2.70 e Å−3 |
415 parameters | Δρmin = −1.89 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.30400 (6) | 0.83549 (8) | 0.19418 (4) | 0.0296 (3) | |
Ag2 | 0.19133 (6) | 1.03934 (8) | 0.25579 (4) | 0.0301 (3) | |
N1 | 0.2935 (6) | 0.6974 (8) | 0.2706 (4) | 0.0255 (19) | |
N2 | 0.6866 (6) | 0.4901 (9) | 0.3732 (5) | 0.029 (2) | |
N3 | 0.4482 (7) | 0.7530 (10) | 0.3296 (4) | 0.037 (2) | |
H3 | 0.4585 | 0.7873 | 0.2929 | 0.045* | |
N4 | −0.1876 (6) | 0.7099 (8) | 0.3036 (4) | 0.0268 (19) | |
N5 | 0.2011 (6) | 0.9267 (9) | 0.3454 (5) | 0.029 (2) | |
N6 | −0.0305 (7) | 0.6806 (9) | 0.3627 (5) | 0.031 (2) | |
H6 | −0.0245 | 0.6207 | 0.3338 | 0.037* | |
C1 | 0.2165 (9) | 0.6290 (13) | 0.2671 (7) | 0.045 (3) | |
H1 | 0.1679 | 0.6390 | 0.2273 | 0.053* | |
C2 | 0.1944 (9) | 0.5454 (12) | 0.3110 (7) | 0.041 (3) | |
H2 | 0.1341 | 0.5008 | 0.3038 | 0.049* | |
C3 | 0.2670 (9) | 0.5300 (13) | 0.3677 (7) | 0.045 (3) | |
H3A | 0.2579 | 0.4718 | 0.4012 | 0.055* | |
C4 | 0.3531 (10) | 0.5987 (12) | 0.3761 (6) | 0.041 (3) | |
H4 | 0.4029 | 0.5883 | 0.4152 | 0.050* | |
C5 | 0.3656 (8) | 0.6842 (10) | 0.3259 (5) | 0.028 (2) | |
C6 | 0.5209 (9) | 0.7732 (12) | 0.3911 (6) | 0.041 (3) | |
H6A | 0.4884 | 0.7677 | 0.4288 | 0.050* | |
H6B | 0.5474 | 0.8613 | 0.3908 | 0.050* | |
C7 | 0.6058 (8) | 0.6777 (10) | 0.4031 (5) | 0.027 (2) | |
C8 | 0.6852 (8) | 0.6987 (10) | 0.4541 (6) | 0.030 (2) | |
H8 | 0.6856 | 0.7712 | 0.4821 | 0.036* | |
C9 | 0.7637 (8) | 0.6182 (11) | 0.4657 (5) | 0.031 (2) | |
H9 | 0.8177 | 0.6327 | 0.5017 | 0.038* | |
C10 | 0.7620 (8) | 0.5156 (11) | 0.4235 (5) | 0.028 (2) | |
H10 | 0.8170 | 0.4603 | 0.4305 | 0.034* | |
C11 | 0.6099 (8) | 0.5723 (11) | 0.3626 (5) | 0.030 (2) | |
H11 | 0.5568 | 0.5571 | 0.3260 | 0.036* | |
C12 | −0.2713 (9) | 0.7802 (10) | 0.2889 (6) | 0.031 (2) | |
H12 | −0.3248 | 0.7489 | 0.2562 | 0.037* | |
C13 | −0.2807 (10) | 0.8951 (12) | 0.3200 (7) | 0.044 (3) | |
H13 | −0.3400 | 0.9421 | 0.3097 | 0.053* | |
C14 | −0.2031 (10) | 0.9394 (11) | 0.3658 (6) | 0.042 (3) | |
H14 | −0.2082 | 1.0195 | 0.3868 | 0.051* | |
C15 | −0.1179 (9) | 0.8727 (10) | 0.3827 (5) | 0.030 (3) | |
H15 | −0.0641 | 0.9046 | 0.4151 | 0.036* | |
C16 | −0.1127 (8) | 0.7554 (10) | 0.3505 (6) | 0.030 (2) | |
C17 | 0.0462 (9) | 0.6965 (11) | 0.4212 (6) | 0.035 (3) | |
H17A | 0.0770 | 0.6118 | 0.4336 | 0.041* | |
H17B | 0.0171 | 0.7252 | 0.4581 | 0.041* | |
C18 | 0.1260 (7) | 0.7931 (9) | 0.4138 (5) | 0.024 (2) | |
C19 | 0.1999 (8) | 0.8217 (10) | 0.4677 (5) | 0.028 (2) | |
H19 | 0.1992 | 0.7871 | 0.5102 | 0.034* | |
C20 | 0.2750 (9) | 0.9011 (11) | 0.4598 (6) | 0.034 (3) | |
H20 | 0.3263 | 0.9219 | 0.4966 | 0.040* | |
C21 | 0.2744 (8) | 0.9506 (10) | 0.3966 (5) | 0.029 (2) | |
H21 | 0.3273 | 1.0021 | 0.3904 | 0.034* | |
C22 | 0.1266 (8) | 0.8491 (10) | 0.3534 (5) | 0.027 (2) | |
H22 | 0.0740 | 0.8333 | 0.3165 | 0.032* | |
S1 | 0.03282 (18) | 0.8243 (2) | 0.12350 (13) | 0.0236 (5) | |
O1 | 0.1186 (5) | 0.7565 (7) | 0.1159 (4) | 0.0321 (17) | |
O2 | 0.0432 (6) | 0.8922 (7) | 0.1865 (4) | 0.0351 (18) | |
O3 | −0.0157 (6) | 0.8948 (7) | 0.0660 (4) | 0.0353 (18) | |
C23 | −0.0529 (8) | 0.6965 (11) | 0.1288 (6) | 0.033 (3) | |
F1 | −0.1388 (5) | 0.7438 (7) | 0.1347 (4) | 0.0483 (19) | |
F2 | −0.0687 (6) | 0.6231 (7) | 0.0747 (4) | 0.0506 (19) | |
F3 | −0.0193 (5) | 0.6218 (7) | 0.1815 (4) | 0.0451 (18) | |
S2 | 0.4912 (2) | 0.6737 (3) | 0.15718 (15) | 0.0355 (7) | |
O4 | 0.5019 (6) | 0.7902 (9) | 0.1973 (4) | 0.043 (2) | |
O5 | 0.3907 (6) | 0.6430 (10) | 0.1279 (5) | 0.053 (2) | |
O6 | 0.5539 (7) | 0.5725 (8) | 0.1845 (4) | 0.046 (2) | |
C24 | 0.5353 (10) | 0.7271 (13) | 0.0856 (7) | 0.046 (3) | |
F4 | 0.6289 (5) | 0.7586 (8) | 0.1038 (4) | 0.056 (2) | |
F5 | 0.4872 (7) | 0.8264 (8) | 0.0557 (4) | 0.067 (3) | |
F6 | 0.5285 (6) | 0.6260 (8) | 0.0427 (4) | 0.055 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0285 (4) | 0.0302 (5) | 0.0323 (5) | 0.0106 (3) | 0.0116 (3) | 0.0109 (3) |
Ag2 | 0.0345 (5) | 0.0296 (5) | 0.0286 (5) | 0.0019 (3) | 0.0124 (3) | 0.0066 (3) |
N1 | 0.028 (5) | 0.018 (4) | 0.032 (5) | 0.009 (4) | 0.010 (4) | 0.006 (4) |
N2 | 0.024 (5) | 0.033 (5) | 0.030 (5) | 0.002 (4) | 0.010 (4) | −0.003 (4) |
N3 | 0.042 (6) | 0.049 (6) | 0.020 (5) | 0.014 (5) | 0.006 (4) | 0.017 (4) |
N4 | 0.033 (5) | 0.024 (4) | 0.027 (5) | −0.002 (4) | 0.014 (4) | −0.001 (4) |
N5 | 0.019 (4) | 0.031 (5) | 0.036 (5) | −0.001 (4) | 0.006 (4) | 0.001 (4) |
N6 | 0.034 (5) | 0.024 (5) | 0.035 (5) | −0.011 (4) | 0.005 (4) | −0.001 (4) |
C1 | 0.031 (7) | 0.047 (8) | 0.052 (8) | 0.006 (6) | 0.002 (6) | 0.005 (6) |
C2 | 0.038 (7) | 0.034 (7) | 0.055 (8) | 0.001 (5) | 0.018 (6) | 0.005 (6) |
C3 | 0.037 (7) | 0.052 (8) | 0.054 (8) | 0.007 (6) | 0.024 (6) | 0.022 (7) |
C4 | 0.047 (7) | 0.039 (7) | 0.039 (7) | 0.026 (6) | 0.011 (6) | 0.017 (6) |
C5 | 0.027 (5) | 0.027 (6) | 0.034 (6) | 0.014 (4) | 0.015 (5) | 0.001 (4) |
C6 | 0.046 (7) | 0.040 (7) | 0.037 (7) | 0.015 (6) | 0.005 (6) | −0.004 (5) |
C7 | 0.026 (5) | 0.029 (6) | 0.026 (5) | 0.002 (4) | 0.008 (4) | 0.003 (4) |
C8 | 0.033 (6) | 0.025 (5) | 0.035 (6) | −0.009 (5) | 0.015 (5) | 0.001 (5) |
C9 | 0.029 (6) | 0.041 (6) | 0.022 (5) | −0.004 (5) | 0.004 (4) | −0.001 (5) |
C10 | 0.025 (5) | 0.037 (6) | 0.024 (5) | 0.002 (5) | 0.008 (4) | 0.003 (5) |
C11 | 0.027 (6) | 0.034 (6) | 0.030 (6) | −0.018 (5) | 0.008 (5) | 0.001 (5) |
C12 | 0.042 (6) | 0.024 (5) | 0.035 (6) | 0.003 (5) | 0.026 (5) | 0.010 (5) |
C13 | 0.054 (8) | 0.028 (6) | 0.061 (8) | −0.001 (6) | 0.037 (7) | −0.004 (6) |
C14 | 0.066 (9) | 0.024 (6) | 0.047 (7) | −0.017 (6) | 0.034 (7) | −0.011 (5) |
C15 | 0.048 (7) | 0.017 (5) | 0.029 (6) | −0.017 (5) | 0.020 (5) | −0.010 (4) |
C16 | 0.032 (6) | 0.027 (6) | 0.036 (6) | −0.004 (5) | 0.014 (5) | 0.001 (5) |
C17 | 0.039 (5) | 0.029 (5) | 0.036 (5) | −0.015 (4) | 0.008 (4) | 0.010 (4) |
C18 | 0.025 (5) | 0.009 (4) | 0.035 (6) | 0.000 (4) | 0.003 (4) | 0.000 (4) |
C19 | 0.043 (6) | 0.021 (5) | 0.020 (5) | 0.001 (5) | 0.006 (5) | 0.004 (4) |
C20 | 0.039 (6) | 0.026 (6) | 0.034 (6) | −0.004 (5) | 0.006 (5) | −0.002 (5) |
C21 | 0.024 (5) | 0.031 (6) | 0.031 (6) | 0.001 (4) | 0.008 (5) | 0.004 (5) |
C22 | 0.033 (6) | 0.021 (5) | 0.027 (5) | −0.003 (4) | 0.008 (5) | −0.003 (4) |
S1 | 0.0243 (12) | 0.0202 (12) | 0.0250 (13) | −0.0021 (10) | 0.0031 (10) | 0.0036 (10) |
O1 | 0.024 (4) | 0.036 (4) | 0.039 (4) | 0.004 (3) | 0.014 (3) | 0.006 (4) |
O2 | 0.044 (5) | 0.029 (4) | 0.033 (4) | −0.009 (4) | 0.009 (4) | −0.006 (3) |
O3 | 0.042 (5) | 0.027 (4) | 0.035 (4) | 0.004 (3) | 0.005 (4) | 0.013 (3) |
C23 | 0.029 (6) | 0.026 (6) | 0.043 (7) | −0.004 (5) | 0.009 (5) | 0.002 (5) |
F1 | 0.022 (3) | 0.051 (4) | 0.074 (5) | −0.002 (3) | 0.016 (3) | 0.013 (4) |
F2 | 0.065 (5) | 0.036 (4) | 0.049 (4) | −0.012 (4) | 0.008 (4) | −0.020 (3) |
F3 | 0.039 (4) | 0.034 (4) | 0.061 (5) | −0.001 (3) | 0.008 (3) | 0.026 (3) |
S2 | 0.0376 (16) | 0.0334 (15) | 0.0401 (16) | 0.0023 (12) | 0.0185 (13) | 0.0078 (12) |
O4 | 0.039 (5) | 0.052 (5) | 0.039 (5) | 0.014 (4) | 0.013 (4) | −0.014 (4) |
O5 | 0.036 (5) | 0.060 (6) | 0.068 (7) | −0.017 (4) | 0.020 (5) | −0.007 (5) |
O6 | 0.078 (7) | 0.029 (4) | 0.034 (5) | 0.014 (4) | 0.017 (4) | 0.005 (4) |
C24 | 0.050 (8) | 0.045 (8) | 0.044 (7) | 0.006 (6) | 0.015 (6) | 0.009 (6) |
F4 | 0.046 (4) | 0.057 (5) | 0.077 (6) | −0.020 (4) | 0.039 (4) | −0.005 (4) |
F5 | 0.090 (7) | 0.061 (5) | 0.054 (5) | 0.032 (5) | 0.029 (5) | 0.038 (4) |
F6 | 0.070 (5) | 0.056 (5) | 0.041 (4) | 0.014 (4) | 0.016 (4) | −0.016 (4) |
Ag1—N2i | 2.151 (9) | C9—H9 | 0.9500 |
Ag1—N1 | 2.164 (9) | C10—H10 | 0.9500 |
Ag1—Ag2 | 3.0897 (12) | C11—H11 | 0.9500 |
Ag2—N4ii | 2.151 (9) | C12—C13 | 1.378 (17) |
Ag2—N5 | 2.169 (9) | C12—H12 | 0.9500 |
N1—C1 | 1.286 (16) | C13—C14 | 1.36 (2) |
N1—C5 | 1.355 (14) | C13—H13 | 0.9500 |
N2—C10 | 1.336 (14) | C14—C15 | 1.362 (18) |
N2—C11 | 1.357 (15) | C14—H14 | 0.9500 |
N2—Ag1iii | 2.151 (9) | C15—C16 | 1.399 (15) |
N3—C5 | 1.354 (15) | C15—H15 | 0.9500 |
N3—C6 | 1.458 (15) | C17—C18 | 1.541 (14) |
N3—H3 | 0.8800 | C17—H17A | 0.9900 |
N4—C16 | 1.348 (14) | C17—H17B | 0.9900 |
N4—C12 | 1.363 (14) | C18—C19 | 1.376 (15) |
N4—Ag2iv | 2.151 (9) | C18—C22 | 1.378 (15) |
N5—C21 | 1.325 (14) | C19—C20 | 1.382 (16) |
N5—C22 | 1.364 (14) | C19—H19 | 0.9500 |
N6—C16 | 1.371 (15) | C20—C21 | 1.401 (16) |
N6—C17 | 1.437 (14) | C20—H20 | 0.9500 |
N6—H6 | 0.8800 | C21—H21 | 0.9500 |
C1—C2 | 1.343 (19) | C22—H22 | 0.9500 |
C1—H1 | 0.9500 | S1—O3 | 1.432 (8) |
C2—C3 | 1.380 (19) | S1—O1 | 1.439 (8) |
C2—H2 | 0.9500 | S1—O2 | 1.459 (8) |
C3—C4 | 1.385 (19) | S1—C23 | 1.817 (11) |
C3—H3A | 0.9500 | C23—F2 | 1.331 (14) |
C4—C5 | 1.406 (16) | C23—F3 | 1.335 (13) |
C4—H4 | 0.9500 | C23—F1 | 1.338 (13) |
C6—C7 | 1.532 (15) | S2—O6 | 1.408 (9) |
C6—H6A | 0.9900 | S2—O5 | 1.445 (9) |
C6—H6B | 0.9900 | S2—O4 | 1.457 (9) |
C7—C8 | 1.370 (15) | S2—C24 | 1.815 (13) |
C7—C11 | 1.388 (16) | C24—F5 | 1.312 (15) |
C8—C9 | 1.365 (16) | C24—F4 | 1.329 (15) |
C8—H8 | 0.9500 | C24—F6 | 1.365 (16) |
C9—C10 | 1.374 (16) | ||
N2i—Ag1—N1 | 173.2 (3) | N4—C12—C13 | 122.1 (12) |
N2i—Ag1—Ag2 | 82.3 (2) | N4—C12—H12 | 118.9 |
N1—Ag1—Ag2 | 91.7 (2) | C13—C12—H12 | 118.9 |
N4ii—Ag2—N5 | 157.1 (3) | C14—C13—C12 | 118.1 (13) |
N4ii—Ag2—Ag1 | 106.3 (2) | C14—C13—H13 | 120.9 |
N5—Ag2—Ag1 | 92.4 (2) | C12—C13—H13 | 120.9 |
C1—N1—C5 | 117.0 (10) | C13—C14—C15 | 122.2 (11) |
C1—N1—Ag1 | 121.4 (8) | C13—C14—H14 | 118.9 |
C5—N1—Ag1 | 121.4 (7) | C15—C14—H14 | 118.9 |
C10—N2—C11 | 117.8 (9) | C14—C15—C16 | 117.3 (11) |
C10—N2—Ag1iii | 119.9 (7) | C14—C15—H15 | 121.3 |
C11—N2—Ag1iii | 122.0 (7) | C16—C15—H15 | 121.3 |
C5—N3—C6 | 123.5 (10) | N4—C16—N6 | 115.2 (9) |
C5—N3—H3 | 118.3 | N4—C16—C15 | 122.1 (10) |
C6—N3—H3 | 118.3 | N6—C16—C15 | 122.6 (10) |
C16—N4—C12 | 118.0 (9) | N6—C17—C18 | 114.8 (9) |
C16—N4—Ag2iv | 127.9 (7) | N6—C17—H17A | 108.6 |
C12—N4—Ag2iv | 114.0 (7) | C18—C17—H17A | 108.6 |
C21—N5—C22 | 119.9 (9) | N6—C17—H17B | 108.6 |
C21—N5—Ag2 | 117.9 (7) | C18—C17—H17B | 108.6 |
C22—N5—Ag2 | 121.3 (7) | H17A—C17—H17B | 107.5 |
C16—N6—C17 | 122.3 (10) | C19—C18—C22 | 119.0 (10) |
C16—N6—H6 | 118.9 | C19—C18—C17 | 119.8 (9) |
C17—N6—H6 | 118.9 | C22—C18—C17 | 121.2 (9) |
N1—C1—C2 | 129.9 (13) | C18—C19—C20 | 119.5 (10) |
N1—C1—H1 | 115.1 | C18—C19—H19 | 120.2 |
C2—C1—H1 | 115.1 | C20—C19—H19 | 120.2 |
C1—C2—C3 | 114.1 (12) | C19—C20—C21 | 119.1 (10) |
C1—C2—H2 | 123.0 | C19—C20—H20 | 120.4 |
C3—C2—H2 | 123.0 | C21—C20—H20 | 120.4 |
C2—C3—C4 | 120.6 (12) | N5—C21—C20 | 121.0 (10) |
C2—C3—H3A | 119.7 | N5—C21—H21 | 119.5 |
C4—C3—H3A | 119.7 | C20—C21—H21 | 119.5 |
C3—C4—C5 | 119.0 (11) | N5—C22—C18 | 121.4 (10) |
C3—C4—H4 | 120.5 | N5—C22—H22 | 119.3 |
C5—C4—H4 | 120.5 | C18—C22—H22 | 119.3 |
N3—C5—N1 | 117.8 (9) | O3—S1—O1 | 114.7 (5) |
N3—C5—C4 | 122.8 (10) | O3—S1—O2 | 115.2 (5) |
N1—C5—C4 | 119.4 (11) | O1—S1—O2 | 114.6 (5) |
N3—C6—C7 | 114.7 (10) | O3—S1—C23 | 103.0 (5) |
N3—C6—H6A | 108.6 | O1—S1—C23 | 103.6 (5) |
C7—C6—H6A | 108.6 | O2—S1—C23 | 103.6 (5) |
N3—C6—H6B | 108.6 | F2—C23—F3 | 108.3 (9) |
C7—C6—H6B | 108.6 | F2—C23—F1 | 107.7 (9) |
H6A—C6—H6B | 107.6 | F3—C23—F1 | 107.5 (9) |
C8—C7—C11 | 116.8 (10) | F2—C23—S1 | 110.9 (8) |
C8—C7—C6 | 119.6 (10) | F3—C23—S1 | 110.9 (8) |
C11—C7—C6 | 123.5 (10) | F1—C23—S1 | 111.3 (8) |
C9—C8—C7 | 121.8 (11) | O6—S2—O5 | 118.1 (6) |
C9—C8—H8 | 119.1 | O6—S2—O4 | 114.7 (5) |
C7—C8—H8 | 119.1 | O5—S2—O4 | 112.9 (6) |
C8—C9—C10 | 117.9 (10) | O6—S2—C24 | 104.9 (6) |
C8—C9—H9 | 121.1 | O5—S2—C24 | 102.1 (6) |
C10—C9—H9 | 121.1 | O4—S2—C24 | 101.5 (6) |
N2—C10—C9 | 123.0 (10) | F5—C24—F4 | 108.3 (11) |
N2—C10—H10 | 118.5 | F5—C24—F6 | 110.3 (11) |
C9—C10—H10 | 118.5 | F4—C24—F6 | 107.1 (11) |
N2—C11—C7 | 122.7 (10) | F5—C24—S2 | 112.9 (9) |
N2—C11—H11 | 118.7 | F4—C24—S2 | 110.2 (9) |
C7—C11—H11 | 118.7 | F6—C24—S2 | 107.8 (9) |
N2i—Ag1—Ag2—N4ii | 0.5 (3) | C12—C13—C14—C15 | −1.5 (19) |
N1—Ag1—Ag2—N4ii | 177.3 (3) | C13—C14—C15—C16 | 0.4 (17) |
N2i—Ag1—Ag2—N5 | −166.0 (3) | C12—N4—C16—N6 | −179.8 (9) |
N1—Ag1—Ag2—N5 | 10.9 (3) | Ag2iv—N4—C16—N6 | −2.3 (14) |
N2i—Ag1—N1—C1 | 110 (3) | C12—N4—C16—C15 | −1.6 (15) |
Ag2—Ag1—N1—C1 | 82.1 (9) | Ag2iv—N4—C16—C15 | 175.8 (8) |
N2i—Ag1—N1—C5 | −67 (3) | C17—N6—C16—N4 | −164.2 (9) |
Ag2—Ag1—N1—C5 | −94.4 (7) | C17—N6—C16—C15 | 17.7 (16) |
N4ii—Ag2—N5—C21 | −51.1 (13) | C14—C15—C16—N4 | 1.2 (16) |
Ag1—Ag2—N5—C21 | 93.7 (8) | C14—C15—C16—N6 | 179.2 (10) |
N4ii—Ag2—N5—C22 | 118.2 (10) | C16—N6—C17—C18 | −89.4 (13) |
Ag1—Ag2—N5—C22 | −96.9 (8) | N6—C17—C18—C19 | 176.1 (10) |
C5—N1—C1—C2 | 1 (2) | N6—C17—C18—C22 | −5.8 (16) |
Ag1—N1—C1—C2 | −175.3 (12) | C22—C18—C19—C20 | −2.8 (15) |
N1—C1—C2—C3 | −1 (2) | C17—C18—C19—C20 | 175.3 (10) |
C1—C2—C3—C4 | 0.9 (19) | C18—C19—C20—C21 | −0.2 (16) |
C2—C3—C4—C5 | −0.3 (19) | C22—N5—C21—C20 | −2.4 (16) |
C6—N3—C5—N1 | 164.4 (10) | Ag2—N5—C21—C20 | 167.1 (8) |
C6—N3—C5—C4 | −16.9 (17) | C19—C20—C21—N5 | 2.8 (17) |
C1—N1—C5—N3 | 178.2 (11) | C21—N5—C22—C18 | −0.7 (15) |
Ag1—N1—C5—N3 | −5.1 (13) | Ag2—N5—C22—C18 | −169.8 (8) |
C1—N1—C5—C4 | −0.5 (15) | C19—C18—C22—N5 | 3.3 (15) |
Ag1—N1—C5—C4 | 176.2 (8) | C17—C18—C22—N5 | −174.8 (10) |
C3—C4—C5—N3 | −178.6 (11) | O3—S1—C23—F2 | 61.0 (9) |
C3—C4—C5—N1 | 0.0 (17) | O1—S1—C23—F2 | −58.8 (9) |
C5—N3—C6—C7 | 95.1 (14) | O2—S1—C23—F2 | −178.7 (8) |
N3—C6—C7—C8 | 170.4 (10) | O3—S1—C23—F3 | −178.7 (8) |
N3—C6—C7—C11 | −6.0 (17) | O1—S1—C23—F3 | 61.6 (9) |
C11—C7—C8—C9 | −1.6 (16) | O2—S1—C23—F3 | −58.3 (9) |
C6—C7—C8—C9 | −178.3 (11) | O3—S1—C23—F1 | −59.0 (9) |
C7—C8—C9—C10 | 1.4 (17) | O1—S1—C23—F1 | −178.7 (8) |
C11—N2—C10—C9 | 2.0 (16) | O2—S1—C23—F1 | 61.3 (9) |
Ag1iii—N2—C10—C9 | 175.4 (8) | O6—S2—C24—F5 | −177.0 (10) |
C8—C9—C10—N2 | −1.6 (17) | O5—S2—C24—F5 | 59.3 (11) |
C10—N2—C11—C7 | −2.3 (15) | O4—S2—C24—F5 | −57.4 (11) |
Ag1iii—N2—C11—C7 | −175.5 (8) | O6—S2—C24—F4 | −55.7 (11) |
C8—C7—C11—N2 | 2.1 (16) | O5—S2—C24—F4 | −179.3 (9) |
C6—C7—C11—N2 | 178.7 (11) | O4—S2—C24—F4 | 64.0 (10) |
C16—N4—C12—C13 | 0.5 (15) | O6—S2—C24—F6 | 60.9 (10) |
Ag2iv—N4—C12—C13 | −177.3 (9) | O5—S2—C24—F6 | −62.8 (10) |
N4—C12—C13—C14 | 1.1 (17) | O4—S2—C24—F6 | −179.5 (8) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O4 | 0.88 | 2.20 | 3.021 (12) | 156 |
N6—H6···O2iv | 0.88 | 2.42 | 3.159 (12) | 142 |
C1—H1···O1 | 0.95 | 2.56 | 3.389 (16) | 146 |
C6—H6A···F6v | 0.99 | 2.55 | 3.282 (15) | 131 |
C9—H9···O3vi | 0.95 | 2.44 | 3.329 (14) | 156 |
C10—H10···O1iii | 0.95 | 2.57 | 3.373 (14) | 142 |
C12—H12···O4vii | 0.95 | 2.51 | 3.331 (15) | 145 |
C17—H17A···O3iv | 0.99 | 2.42 | 3.186 (14) | 134 |
C21—H21···F6i | 0.95 | 2.54 | 3.325 (14) | 140 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x+1, −y+3/2, z+1/2; (vii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C11H11N3)](CF3O3S) |
Mr | 442.17 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 14.0965 (10), 10.4007 (7), 20.6593 (15) |
β (°) | 102.994 (1) |
V (Å3) | 2951.4 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.56 |
Crystal size (mm) | 0.30 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.652, 0.697 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16169, 5797, 4479 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.088, 0.238, 1.09 |
No. of reflections | 5797 |
No. of parameters | 415 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.1255P)2 + 38.027P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 2.70, −1.89 |
Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O4 | 0.88 | 2.20 | 3.021 (12) | 156 |
N6—H6···O2i | 0.88 | 2.42 | 3.159 (12) | 142 |
C1—H1···O1 | 0.95 | 2.56 | 3.389 (16) | 146 |
C6—H6A···F6ii | 0.99 | 2.55 | 3.282 (15) | 131 |
C9—H9···O3iii | 0.95 | 2.44 | 3.329 (14) | 156 |
C10—H10···O1iv | 0.95 | 2.57 | 3.373 (14) | 142 |
C12—H12···O4v | 0.95 | 2.51 | 3.331 (15) | 145 |
C17—H17A···O3i | 0.99 | 2.42 | 3.186 (14) | 134 |
C21—H21···F6vi | 0.95 | 2.54 | 3.325 (14) | 140 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1, −y+3/2, z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x−1, y, z; (vi) −x+1, y+1/2, −z+1/2. |
Acknowledgements
This work was supported by NRF (2010–0022675 and 2012R1A4A1027750) projects.
References
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Germany. Google Scholar
Bruker. (2000). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Silver coordination polymers based on dipyridyl type ligands have attracted particular interest because of the intriguing architectures caused by a variety of coordination geometries for the Ag(I) cation as well as their potential applications as functional materials (Leong & Vittal, 2011; Moulton & Zaworotko, 2001). However, despite the rapid growth in the Ag(I) coordination chemistry based on symmetrical dipyridyl ligands, investigations using unsymmetrical dipyridyl ligands with nitrogen donor atoms in different positions on the two terminal pyridines still remains lacking. Herein, we report the crystal structure of the title compound prepared by the reaction of silver trifluoromethanesulfonate with the unsymmetrical dipyridyl ligand. The structure of title compound is isostructural with the perchlorate salt (Zhang et al., 2013).
The asymmetric unit of the title compound contains two AgI atoms (Ag1 and Ag2), two N-(pyridin-3-ylmethyl)pyridine-2-amine (Foxon et al., 2002; Lee et al., 2008) ligands (A and B) and two CF3SO3- anions. The Ag1 atom is coordinated by two pyridine N atoms from two symmetry-related ligand A in a geometry slightly distorted from linear [N–Ag1–N = 173.2 (3)°] to form left-handed helical chain, while the Ag2 atom is coordinated by two pyridine N atoms from two symmetry-related ligand B in a bent arrangement [N–Ag2–N = 157.1 (3)°] to form right-handed helical chain (Fig. 1). Two pyridine rings coordinated to the Ag1 and Ag2 centers are tilted by 14.2 (7)° and 34.1 (5)°, respectively, with respect to each other. Both helical chains with the same pitch length of 10.4007 (7) Å propagate along the b axis and are alternately arranged via the Ag···Ag interactions [3.0897 (12) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane. Furthermore, π–π stacking interactions [centroid-centroid distances = 3.564 (7) and 3.518 (6) Å] between pyridine rings of both helical chains, as shown in Fig. 2, contribute to stabilize the two-dimensional network.
The non-coordinating CF3SO3- anions participate in N–H···O hydrogen bonding (Table 1, Fig. 2) and Ag···O interactions (Ag1···O4 2.815 (8), Ag1···O5 2.852 (10), Ag1···O1 2.867 (8), Ag2···O2 2.722 (8) Å) (Fig. 1,2). In addition, C–H···O and C–H···F hydrogen bonds (Table 1) between the helical chains and anions are also detected in the crystal.