Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011565/om6146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011565/om6146Isup2.hkl |
CCDC reference: 217356
A solution of Ag(CF3SO3) (0.13 g, 0.5 mmol) in H2O (10 ml) was added slowly to a stirring solution of bpe (0.10 g, 0.50 mmol) in methanol (20 ml), the reaction mixture was stirred for 3 h at room temperature and gave a colorless solution which was filtered. The colorless crystals of the title compound were obtained by keeping the resulting solution in air for one week.
The positions of all H atoms were generated geometrically (C—H bond fixed at 0.96 Å), assigned isoptropic displacement parameters and allowed to ride on their respective parent C atoms before the final cycle of least-squares refinement.
Data collection: SMART (Siemens, 1994); cell refinement: SMART; data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
[Ag(C12H12N2)](CF3O3S) | F(000) = 1744 |
Mr = 441.18 | Dx = 1.878 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8575 (15) Å | Cell parameters from 5201 reflections |
b = 15.195 (2) Å | θ = 2.8–27.6° |
c = 20.974 (3) Å | µ = 1.47 mm−1 |
β = 96.654 (4)° | T = 293 K |
V = 3120.4 (8) Å3 | Needle, colorless |
Z = 8 | 0.46 × 0.32 × 0.25 mm |
Siemens SMART CCD diffractometer | 7176 independent reflections |
Radiation source: fine-focus sealed tube | 2940 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ω scans | θmax = 27.6°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.574, Tmax = 0.692 | k = −18→19 |
21114 measured reflections | l = −27→18 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0132P)2] where P = (Fo2 + 2Fc2)/3 |
7176 reflections | (Δ/σ)max = 0.004 |
415 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
[Ag(C12H12N2)](CF3O3S) | V = 3120.4 (8) Å3 |
Mr = 441.18 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.8575 (15) Å | µ = 1.47 mm−1 |
b = 15.195 (2) Å | T = 293 K |
c = 20.974 (3) Å | 0.46 × 0.32 × 0.25 mm |
β = 96.654 (4)° |
Siemens SMART CCD diffractometer | 7176 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2940 reflections with I > 2σ(I) |
Tmin = 0.574, Tmax = 0.692 | Rint = 0.067 |
21114 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.53 e Å−3 |
7176 reflections | Δρmin = −0.55 e Å−3 |
415 parameters |
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. Eight low-angle reflections omitted. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.40467 (4) | 0.45484 (3) | 0.058762 (19) | 0.06985 (16) | |
Ag2 | −0.63954 (4) | 0.36891 (3) | −0.42253 (2) | 0.06922 (16) | |
N1 | 1.1916 (4) | 0.3960 (3) | 0.5044 (2) | 0.0547 (12) | |
N2 | 0.5614 (3) | 0.4471 (3) | 0.13918 (17) | 0.0457 (10) | |
N3 | 0.2278 (3) | 0.4505 (3) | −0.01102 (18) | 0.0543 (11) | |
N4 | −0.4614 (4) | 0.3858 (3) | −0.35279 (19) | 0.0541 (11) | |
S1 | 0.84245 (15) | 0.75924 (11) | 0.32770 (7) | 0.0659 (4) | |
S2 | −0.42402 (14) | 0.21579 (10) | −0.52218 (7) | 0.0617 (4) | |
O1 | 0.8519 (4) | 0.6657 (3) | 0.3294 (2) | 0.1180 (16) | |
O2 | 0.9701 (3) | 0.8018 (3) | 0.32673 (19) | 0.1005 (14) | |
O3 | 0.7558 (4) | 0.7943 (3) | 0.3697 (2) | 0.1188 (16) | |
O4 | −0.4474 (4) | 0.1341 (2) | −0.5555 (2) | 0.1071 (15) | |
O5 | −0.5149 (3) | 0.2316 (2) | −0.47487 (16) | 0.0707 (10) | |
O6 | −0.2853 (3) | 0.2361 (2) | −0.50267 (19) | 0.0946 (13) | |
F1 | 0.7366 (4) | 0.8629 (3) | 0.23702 (19) | 0.1500 (18) | |
F2 | 0.8236 (4) | 0.7480 (3) | 0.20393 (17) | 0.1232 (14) | |
F3 | 0.6341 (3) | 0.7435 (3) | 0.24095 (17) | 0.1387 (16) | |
F4 | −0.4060 (4) | 0.2903 (3) | −0.6325 (2) | 0.1574 (19) | |
F5 | −0.4506 (4) | 0.3777 (3) | −0.5578 (2) | 0.1343 (16) | |
F6 | −0.6055 (4) | 0.2920 (3) | −0.60159 (17) | 0.1360 (15) | |
C1 | 0.7545 (7) | 0.7801 (5) | 0.2488 (3) | 0.0784 (18) | |
C2 | −0.4715 (7) | 0.2969 (5) | −0.5837 (4) | 0.093 (2) | |
C11 | 1.2069 (5) | 0.4466 (4) | 0.4546 (3) | 0.088 (2) | |
H11A | 1.2918 | 0.4722 | 0.4518 | 0.106* | |
C12 | 1.1034 (5) | 0.4630 (4) | 0.4068 (3) | 0.091 (2) | |
H12A | 1.1199 | 0.4980 | 0.3722 | 0.109* | |
C13 | 0.9761 (5) | 0.4286 (3) | 0.4092 (2) | 0.0525 (14) | |
C14 | 0.8601 (4) | 0.4464 (3) | 0.3565 (2) | 0.0680 (16) | |
H14A | 0.7758 | 0.4243 | 0.3702 | 0.082* | |
H14B | 0.8504 | 0.5096 | 0.3508 | 0.082* | |
C15 | 0.8789 (5) | 0.4071 (4) | 0.2954 (3) | 0.101 (2) | |
H15A | 0.8898 | 0.3441 | 0.3014 | 0.121* | |
H15B | 0.9632 | 0.4296 | 0.2819 | 0.121* | |
C16 | 0.7643 (5) | 0.4230 (4) | 0.2413 (2) | 0.0663 (17) | |
C17 | 0.6752 (6) | 0.3579 (4) | 0.2214 (3) | 0.0839 (19) | |
H17A | 0.6810 | 0.3038 | 0.2422 | 0.101* | |
C18 | 0.5770 (5) | 0.3716 (4) | 0.1709 (3) | 0.0701 (17) | |
H18A | 0.5180 | 0.3256 | 0.1580 | 0.084* | |
C19 | 0.6452 (4) | 0.5114 (3) | 0.1595 (2) | 0.0510 (14) | |
H19A | 0.6354 | 0.5654 | 0.1387 | 0.061* | |
C20 | 0.7472 (5) | 0.5026 (4) | 0.2105 (2) | 0.0609 (16) | |
H20A | 0.8032 | 0.5500 | 0.2236 | 0.073* | |
C21 | 0.9603 (5) | 0.3774 (3) | 0.4595 (2) | 0.0632 (15) | |
H21A | 0.8760 | 0.3516 | 0.4631 | 0.076* | |
C22 | 1.0691 (5) | 0.3623 (3) | 0.5067 (2) | 0.0677 (16) | |
H22A | 1.0548 | 0.3268 | 0.5414 | 0.081* | |
C23 | 0.1742 (5) | 0.3732 (4) | −0.0291 (2) | 0.0697 (16) | |
H23A | 0.2174 | 0.3224 | −0.0124 | 0.084* | |
C24 | 0.0575 (5) | 0.3647 (4) | −0.0716 (3) | 0.0725 (17) | |
H24A | 0.0231 | 0.3090 | −0.0825 | 0.087* | |
C25 | −0.0086 (5) | 0.4384 (4) | −0.0979 (2) | 0.0597 (16) | |
C26 | −0.1376 (5) | 0.4318 (4) | −0.1443 (3) | 0.095 (2) | |
H26A | −0.1994 | 0.3913 | −0.1265 | 0.114* | |
H26B | −0.1812 | 0.4891 | −0.1471 | 0.114* | |
C27 | −0.1214 (5) | 0.4045 (5) | −0.2053 (3) | 0.117 (3) | |
H27A | −0.0785 | 0.3470 | −0.2015 | 0.140* | |
H27B | −0.0562 | 0.4441 | −0.2215 | 0.140* | |
C28 | −0.2420 (5) | 0.3973 (4) | −0.2570 (2) | 0.0637 (16) | |
C29 | −0.2306 (4) | 0.3578 (3) | −0.3129 (2) | 0.0531 (14) | |
H29A | −0.1478 | 0.3328 | −0.3203 | 0.064* | |
C30 | −0.3407 (5) | 0.3537 (3) | −0.3598 (2) | 0.0609 (15) | |
H30A | −0.3286 | 0.3267 | −0.3985 | 0.073* | |
C31 | −0.4720 (5) | 0.4247 (4) | −0.2983 (3) | 0.091 (2) | |
H31A | −0.5560 | 0.4490 | −0.2922 | 0.110* | |
C32 | −0.3679 (5) | 0.4322 (4) | −0.2494 (3) | 0.113 (3) | |
H32A | −0.3822 | 0.4606 | −0.2114 | 0.135* | |
C33 | 0.0490 (5) | 0.5173 (4) | −0.0806 (2) | 0.0573 (15) | |
H33A | 0.0098 | 0.5689 | −0.0980 | 0.069* | |
C34 | 0.1656 (5) | 0.5215 (3) | −0.0372 (2) | 0.0569 (14) | |
H34A | 0.2021 | 0.5764 | −0.0258 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0497 (2) | 0.1013 (4) | 0.0511 (3) | 0.0145 (2) | −0.02595 (19) | −0.0129 (3) |
Ag2 | 0.0489 (2) | 0.0970 (4) | 0.0540 (3) | 0.0090 (2) | −0.0269 (2) | −0.0059 (3) |
N1 | 0.045 (3) | 0.066 (3) | 0.048 (3) | 0.010 (2) | −0.016 (2) | 0.000 (2) |
N2 | 0.039 (2) | 0.053 (3) | 0.041 (3) | 0.006 (2) | −0.0110 (19) | −0.004 (2) |
N3 | 0.047 (2) | 0.060 (3) | 0.051 (3) | 0.007 (2) | −0.016 (2) | 0.000 (3) |
N4 | 0.037 (2) | 0.075 (3) | 0.047 (3) | 0.000 (2) | −0.014 (2) | −0.008 (2) |
S1 | 0.0605 (10) | 0.0791 (13) | 0.0542 (10) | −0.0058 (9) | −0.0104 (8) | −0.0022 (9) |
S2 | 0.0547 (9) | 0.0648 (11) | 0.0621 (11) | −0.0056 (8) | −0.0080 (8) | −0.0072 (8) |
O1 | 0.172 (4) | 0.066 (3) | 0.104 (4) | −0.008 (3) | −0.037 (3) | 0.015 (3) |
O2 | 0.063 (2) | 0.130 (4) | 0.103 (4) | −0.033 (2) | −0.014 (2) | −0.007 (3) |
O3 | 0.090 (3) | 0.194 (5) | 0.071 (3) | 0.023 (3) | 0.005 (3) | −0.032 (3) |
O4 | 0.099 (3) | 0.072 (3) | 0.148 (4) | −0.009 (2) | 0.004 (3) | −0.055 (3) |
O5 | 0.074 (2) | 0.089 (3) | 0.050 (2) | −0.008 (2) | 0.012 (2) | −0.002 (2) |
O6 | 0.053 (2) | 0.105 (3) | 0.118 (4) | −0.014 (2) | −0.024 (2) | 0.008 (3) |
F1 | 0.207 (4) | 0.095 (3) | 0.133 (4) | 0.042 (3) | −0.042 (3) | 0.039 (3) |
F2 | 0.129 (3) | 0.182 (4) | 0.057 (3) | 0.030 (3) | 0.000 (2) | −0.011 (3) |
F3 | 0.081 (2) | 0.225 (5) | 0.099 (3) | −0.027 (3) | −0.039 (2) | 0.009 (3) |
F4 | 0.156 (4) | 0.258 (5) | 0.061 (3) | −0.020 (3) | 0.026 (3) | 0.031 (3) |
F5 | 0.138 (3) | 0.091 (3) | 0.168 (4) | −0.001 (3) | −0.004 (3) | 0.039 (3) |
F6 | 0.095 (3) | 0.207 (4) | 0.096 (3) | 0.010 (3) | −0.033 (2) | 0.033 (3) |
C1 | 0.081 (5) | 0.094 (6) | 0.056 (5) | 0.005 (4) | −0.013 (4) | 0.004 (4) |
C2 | 0.071 (5) | 0.128 (7) | 0.077 (6) | −0.012 (5) | −0.005 (4) | −0.001 (5) |
C11 | 0.046 (3) | 0.132 (6) | 0.079 (5) | −0.024 (4) | −0.024 (3) | 0.027 (4) |
C12 | 0.069 (4) | 0.128 (6) | 0.069 (4) | −0.035 (4) | −0.023 (3) | 0.050 (4) |
C13 | 0.052 (3) | 0.058 (4) | 0.041 (3) | 0.006 (3) | −0.020 (3) | 0.002 (3) |
C14 | 0.056 (3) | 0.093 (4) | 0.049 (4) | 0.006 (3) | −0.023 (3) | 0.008 (3) |
C15 | 0.081 (4) | 0.161 (6) | 0.054 (4) | 0.051 (4) | −0.027 (4) | −0.031 (4) |
C16 | 0.058 (4) | 0.092 (5) | 0.043 (4) | 0.027 (3) | −0.020 (3) | −0.012 (3) |
C17 | 0.120 (5) | 0.061 (4) | 0.060 (4) | 0.025 (4) | −0.036 (4) | 0.005 (3) |
C18 | 0.089 (4) | 0.046 (4) | 0.065 (4) | −0.008 (3) | −0.036 (3) | −0.002 (3) |
C19 | 0.044 (3) | 0.056 (4) | 0.050 (3) | −0.003 (3) | −0.010 (3) | 0.008 (3) |
C20 | 0.043 (3) | 0.085 (5) | 0.050 (4) | −0.014 (3) | −0.014 (3) | −0.017 (3) |
C21 | 0.045 (3) | 0.084 (4) | 0.055 (4) | −0.012 (3) | −0.015 (3) | 0.012 (3) |
C22 | 0.057 (3) | 0.083 (4) | 0.058 (4) | 0.000 (3) | −0.013 (3) | 0.027 (3) |
C23 | 0.071 (4) | 0.064 (4) | 0.065 (4) | 0.018 (3) | −0.028 (3) | 0.000 (3) |
C24 | 0.068 (4) | 0.070 (4) | 0.073 (4) | −0.003 (3) | −0.020 (3) | −0.012 (3) |
C25 | 0.047 (3) | 0.085 (5) | 0.041 (3) | 0.014 (3) | −0.020 (3) | −0.008 (3) |
C26 | 0.062 (4) | 0.154 (6) | 0.060 (4) | 0.011 (4) | −0.031 (3) | −0.018 (4) |
C27 | 0.044 (3) | 0.225 (8) | 0.074 (5) | 0.031 (4) | −0.024 (3) | −0.065 (5) |
C28 | 0.041 (3) | 0.098 (5) | 0.046 (4) | 0.007 (3) | −0.020 (3) | −0.021 (3) |
C29 | 0.035 (3) | 0.071 (4) | 0.049 (4) | 0.005 (3) | −0.010 (2) | −0.012 (3) |
C30 | 0.046 (3) | 0.089 (4) | 0.044 (3) | 0.000 (3) | −0.013 (3) | −0.018 (3) |
C31 | 0.044 (3) | 0.165 (6) | 0.059 (4) | 0.032 (4) | −0.023 (3) | −0.044 (4) |
C32 | 0.052 (4) | 0.198 (7) | 0.080 (5) | 0.036 (4) | −0.026 (3) | −0.083 (5) |
C33 | 0.051 (3) | 0.070 (4) | 0.046 (3) | 0.015 (3) | −0.012 (3) | 0.006 (3) |
C34 | 0.055 (3) | 0.067 (4) | 0.045 (3) | 0.000 (3) | −0.009 (3) | −0.002 (3) |
Ag1—N3 | 2.143 (3) | C15—C16 | 1.524 (6) |
Ag1—N2 | 2.155 (3) | C15—H15A | 0.9700 |
Ag1—O4i | 2.758 (4) | C15—H15B | 0.9700 |
Ag2—N4 | 2.166 (3) | C16—C17 | 1.356 (6) |
Ag2—N1ii | 2.167 (4) | C16—C20 | 1.374 (6) |
Ag2—O5 | 2.717 (3) | C17—C18 | 1.366 (6) |
N1—C22 | 1.317 (5) | C17—H17A | 0.9300 |
N1—C11 | 1.321 (6) | C18—H18A | 0.9300 |
N1—Ag2iii | 2.167 (4) | C19—C20 | 1.386 (6) |
N2—C19 | 1.318 (5) | C19—H19A | 0.9300 |
N2—C18 | 1.326 (5) | C20—H20A | 0.9300 |
N3—C23 | 1.325 (5) | C21—C22 | 1.392 (6) |
N3—C34 | 1.327 (5) | C21—H21A | 0.9300 |
N4—C31 | 1.301 (5) | C22—H22A | 0.9300 |
N4—C30 | 1.310 (5) | C23—C24 | 1.377 (6) |
S1—O3 | 1.402 (4) | C23—H23A | 0.9300 |
S1—O2 | 1.417 (3) | C24—C25 | 1.378 (6) |
S1—O1 | 1.424 (4) | C24—H24A | 0.9300 |
S1—C1 | 1.804 (6) | C25—C33 | 1.359 (6) |
S2—O6 | 1.415 (3) | C25—C26 | 1.512 (5) |
S2—O4 | 1.431 (3) | C26—C27 | 1.372 (6) |
S2—O5 | 1.432 (3) | C26—H26A | 0.9700 |
S2—C2 | 1.806 (7) | C26—H26B | 0.9700 |
F1—C1 | 1.292 (6) | C27—C28 | 1.517 (6) |
F2—C1 | 1.317 (6) | C27—H27A | 0.9700 |
F3—C1 | 1.304 (6) | C27—H27B | 0.9700 |
F4—C2 | 1.278 (7) | C28—C29 | 1.333 (6) |
F5—C2 | 1.348 (7) | C28—C32 | 1.376 (6) |
F6—C2 | 1.333 (6) | C29—C30 | 1.379 (5) |
C11—C12 | 1.368 (6) | C29—H29A | 0.9300 |
C11—H11A | 0.9300 | C30—H30A | 0.9300 |
C12—C13 | 1.366 (6) | C31—C32 | 1.370 (6) |
C12—H12A | 0.9300 | C31—H31A | 0.9300 |
C13—C21 | 1.336 (6) | C32—H32A | 0.9300 |
C13—C14 | 1.519 (5) | C33—C34 | 1.382 (5) |
C14—C15 | 1.446 (6) | C33—H33A | 0.9300 |
C14—H14A | 0.9700 | C34—H34A | 0.9300 |
C14—H14B | 0.9700 | ||
N3—Ag1—N2 | 170.27 (15) | C17—C16—C20 | 117.2 (5) |
N3—Ag1—O4i | 97.37 (15) | C17—C16—C15 | 120.8 (6) |
N2—Ag1—O4i | 88.59 (14) | C20—C16—C15 | 122.0 (5) |
N4—Ag2—N1ii | 161.97 (15) | C16—C17—C18 | 120.2 (5) |
N4—Ag2—O5 | 89.71 (13) | C16—C17—H17A | 119.9 |
N1ii—Ag2—O5 | 101.90 (12) | C18—C17—H17A | 119.9 |
C22—N1—C11 | 116.4 (4) | N2—C18—C17 | 123.5 (5) |
C22—N1—Ag2iii | 122.2 (4) | N2—C18—H18A | 118.3 |
C11—N1—Ag2iii | 121.4 (4) | C17—C18—H18A | 118.3 |
C19—N2—C18 | 116.5 (4) | N2—C19—C20 | 123.3 (5) |
C19—N2—Ag1 | 125.4 (3) | N2—C19—H19A | 118.3 |
C18—N2—Ag1 | 118.1 (3) | C20—C19—H19A | 118.3 |
C23—N3—C34 | 116.9 (4) | C16—C20—C19 | 119.1 (5) |
C23—N3—Ag1 | 119.2 (3) | C16—C20—H20A | 120.4 |
C34—N3—Ag1 | 123.9 (4) | C19—C20—H20A | 120.4 |
C31—N4—C30 | 115.7 (4) | C13—C21—C22 | 120.5 (5) |
C31—N4—Ag2 | 120.4 (3) | C13—C21—H21A | 119.7 |
C30—N4—Ag2 | 123.8 (3) | C22—C21—H21A | 119.7 |
O3—S1—O2 | 116.2 (3) | N1—C22—C21 | 123.0 (5) |
O3—S1—O1 | 114.0 (3) | N1—C22—H22A | 118.5 |
O2—S1—O1 | 113.6 (3) | C21—C22—H22A | 118.5 |
O3—S1—C1 | 104.3 (3) | N3—C23—C24 | 123.0 (5) |
O2—S1—C1 | 103.9 (3) | N3—C23—H23A | 118.5 |
O1—S1—C1 | 102.8 (3) | C24—C23—H23A | 118.5 |
O6—S2—O4 | 115.2 (2) | C23—C24—C25 | 120.2 (5) |
O6—S2—O5 | 115.1 (2) | C23—C24—H24A | 119.9 |
O4—S2—O5 | 113.9 (2) | C25—C24—H24A | 119.9 |
O6—S2—C2 | 102.7 (3) | C33—C25—C24 | 116.5 (4) |
O4—S2—C2 | 103.3 (3) | C33—C25—C26 | 121.7 (5) |
O5—S2—C2 | 104.4 (3) | C24—C25—C26 | 121.8 (5) |
S2—O5—Ag2 | 139.2 (2) | C27—C26—C25 | 116.1 (5) |
F1—C1—F3 | 106.8 (5) | C27—C26—H26A | 108.3 |
F1—C1—F2 | 107.1 (6) | C25—C26—H26A | 108.3 |
F3—C1—F2 | 106.9 (6) | C27—C26—H26B | 108.3 |
F1—C1—S1 | 112.8 (5) | C25—C26—H26B | 108.3 |
F3—C1—S1 | 112.0 (5) | H26A—C26—H26B | 107.4 |
F2—C1—S1 | 110.9 (4) | C26—C27—C28 | 121.5 (5) |
F4—C2—F6 | 110.2 (6) | C26—C27—H27A | 107.0 |
F4—C2—F5 | 109.1 (6) | C28—C27—H27A | 107.0 |
F6—C2—F5 | 105.4 (6) | C26—C27—H27B | 107.0 |
F4—C2—S2 | 113.9 (6) | C28—C27—H27B | 107.0 |
F6—C2—S2 | 109.2 (5) | H27A—C27—H27B | 106.7 |
F5—C2—S2 | 108.7 (5) | C29—C28—C32 | 116.4 (4) |
N1—C11—C12 | 122.8 (5) | C29—C28—C27 | 121.5 (5) |
N1—C11—H11A | 118.6 | C32—C28—C27 | 122.1 (5) |
C12—C11—H11A | 118.6 | C28—C29—C30 | 120.5 (4) |
C13—C12—C11 | 121.0 (5) | C28—C29—H29A | 119.7 |
C13—C12—H12A | 119.5 | C30—C29—H29A | 119.7 |
C11—C12—H12A | 119.5 | N4—C30—C29 | 123.6 (5) |
C21—C13—C12 | 116.3 (4) | N4—C30—H30A | 118.2 |
C21—C13—C14 | 122.2 (5) | C29—C30—H30A | 118.2 |
C12—C13—C14 | 121.5 (5) | N4—C31—C32 | 124.6 (5) |
C15—C14—C13 | 114.1 (4) | N4—C31—H31A | 117.7 |
C15—C14—H14A | 108.7 | C32—C31—H31A | 117.7 |
C13—C14—H14A | 108.7 | C31—C32—C28 | 119.2 (5) |
C15—C14—H14B | 108.7 | C31—C32—H32A | 120.4 |
C13—C14—H14B | 108.7 | C28—C32—H32A | 120.4 |
H14A—C14—H14B | 107.6 | C25—C33—C34 | 120.4 (5) |
C14—C15—C16 | 115.7 (4) | C25—C33—H33A | 119.8 |
C14—C15—H15A | 108.3 | C34—C33—H33A | 119.8 |
C16—C15—H15A | 108.3 | N3—C34—C33 | 123.0 (5) |
C14—C15—H15B | 108.3 | N3—C34—H34A | 118.5 |
C16—C15—H15B | 108.3 | C33—C34—H34A | 118.5 |
H15A—C15—H15B | 107.4 |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x−2, y, z−1; (iii) x+2, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C12H12N2)](CF3O3S) |
Mr | 441.18 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.8575 (15), 15.195 (2), 20.974 (3) |
β (°) | 96.654 (4) |
V (Å3) | 3120.4 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.47 |
Crystal size (mm) | 0.46 × 0.32 × 0.25 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.574, 0.692 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21114, 7176, 2940 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.076, 0.95 |
No. of reflections | 7176 |
No. of parameters | 415 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.55 |
Computer programs: SMART (Siemens, 1994), SMART, SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
Ag1—N3 | 2.143 (3) | Ag2—N4 | 2.166 (3) |
Ag1—N2 | 2.155 (3) | Ag2—N1ii | 2.167 (4) |
Ag1—O4i | 2.758 (4) | Ag2—O5 | 2.717 (3) |
N3—Ag1—N2 | 170.27 (15) | N4—Ag2—N1ii | 161.97 (15) |
N3—Ag1—O4i | 97.37 (15) | N4—Ag2—O5 | 89.71 (13) |
N2—Ag1—O4i | 88.59 (14) | N1ii—Ag2—O5 | 101.90 (12) |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x−2, y, z−1. |
The design and synthesis of supramolecular frameworks has made rapid progress in recent years owing to their intriguing structural diversities and their potential application as functional materials (Eddaoudi et al., 2001; Hagrman et al., 1999; Moulton et al., 2001). Metal–pyridine coordination is an important tool in the construction of these frameworks. A number of pyridine-donor bis-monodentate ligands bearing rigid (Fujita et al., 1995; MacGillivray et al., 1994) or flexible (Carlucci et al., 1997; Hennigar et al., 1997) alkyl and aryl spacers have been extensively employed to develop supramolecular complexes with various structures and functions. 1,2-bis(4-pyridyl)ethane (bpe) can adopt the gauche and anti conformations, which may include supramolecular isomerism in coordination polymers (Fu et al., 2002; Hennigar et al., 1997). Silver(I) is an extremely soft acid and has a good affinity for most coordination atoms in a ligand. The self-assembly of silver(I) with organic ligands can give rise to a variety of supramolecualr complexes, in which silver(I) exhibits a labile coordination modes, such as linear, trigonal, tetrahedral, square-planar, pentagonal, square-pyramidal and even octahedral fashions (LaDuca et al., 2000; Khlobystov et al., 2001; Munakata et al., 1997; Su et al., 2002; Tong et al., 2000). The combination of both can result in some interesting structural topologies (LaDuca et al., 2000). Moreover, the assembly process may be influenced by solvent system, the ratio of metal to ligand, template and counter-ions. Sometimes, the alteration in any of these factors can result in new complexes with different structure and different functions. Here, we wish to report a one-dimensional silver(I) compound {[Ag(bpe)](OTf)}n (OTf = trifluoromethanesulfonate), (I).
Single-crystal X-ray diffraction analysis of (I) reveals that the title compound crystallizes in monoclinic space group P21/c and consists of the slightly distorted linear [Ag(bpe)]n chains and counter anions OTf. As shown in Fig. 1, each AgI center is coordinated by two nitrogen atoms from different bpe in a slightly distorted linear fashion to form a linear chain of alternating AgI and bpe. Ag—N bond distances are in the range from 2.149 (5) to 2.168 (5) Å, which are typical values for AgI—Npy coordination distances (Junior et al., 2000; Khlobystov et al., 2001; Munakata et al., 1997). The bond angles of N3—Ag1—N2 and N4—Ag2—N1A are 170.0 (2) and 161.8 (2)°, respectively, indicative of the presence of a linear distortion in the compound. Bpe acts as an exo-bidentate ligand in an anti conformation to link two-coordinated AgI into a one-dimensional linear chain. The dihedral angles between two pyridyl rings are 37.8 and 62.8° in bpe ligands. The shorter bond distances of C14—C15 [1.446 (6) Å] and C26—C27 [1.372 (6) Å] suggest a conformational disorder in the bridging ethane groups of bpe. Ag···Ag separations across bpe are 13.605 and 13.619 Å. The closest Ag···Ag distance in the adjacent chains is 3.55 Å, which is longer than the summed van der Waals radius of two silver atoms (3.44 Å). It is noteworthy that there are two types of distinctly different OTf, i.e. one only acts as a counter-anion the other not only serves as a counter-anions, but also behaves in a bridging mode to link adjacent chains into a two-dimensional layer structure through weak Ag···O interactions (Fig. 2). [Ag1···O4i = 2.758 (4) Å and Ag2···O5 = 2.717 (3) Å; symmetry code: (i) −x, y + 1/2, −z − 1/2].