Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025146/hg6219sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025146/hg6219Isup2.hkl |
CCDC reference: 287588
1-Phenylsulfanyl-2-(2-pyridylsulfanyl)ethane (L) was prepared according to a reported procedure (Chen et al., 2001). A solution containing a 1:1 molar ratio of AgBF4 (0.2 mmol) and L (0.2 mmol) in acetonitrile–chloroform (1:1) was stirred for 30 min at room temperature, and the mixture was filtered. Colorless single crystals suitable for X-ray investigation were obtained from above filtrate by slow evaporation of the solvent.
All H atoms were positioned geometrically with Csp2—H = 0.93 Å and Csp3—H = 0.97 Å; they were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The BF4− anion was observed to be disordered and was eventually modeled as eight 0.5-occupied F atoms surrounding the central B atom.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
[Ag(C13H13NS2)]BF4 | F(000) = 872 |
Mr = 442.04 | Dx = 1.836 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1006 reflections |
a = 11.252 (3) Å | θ = 3.6–25.8° |
b = 13.999 (4) Å | µ = 1.56 mm−1 |
c = 11.315 (3) Å | T = 293 K |
β = 116.227 (4)° | Block, colorless |
V = 1598.8 (8) Å3 | 0.16 × 0.12 × 0.08 mm |
Z = 4 |
Bruker SMART 1000 CCD diffractometer | 3260 independent reflections |
Radiation source: fine-focus sealed tube | 2324 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→14 |
Tmin = 0.643, Tmax = 0.883 | k = −13→17 |
9039 measured reflections | l = −14→9 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.3971P] where P = (Fo2 + 2Fc2)/3 |
3260 reflections | (Δ/σ)max = 0.004 |
235 parameters | Δρmax = 0.52 e Å−3 |
20 restraints | Δρmin = −0.39 e Å−3 |
[Ag(C13H13NS2)]BF4 | V = 1598.8 (8) Å3 |
Mr = 442.04 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.252 (3) Å | µ = 1.56 mm−1 |
b = 13.999 (4) Å | T = 293 K |
c = 11.315 (3) Å | 0.16 × 0.12 × 0.08 mm |
β = 116.227 (4)° |
Bruker SMART 1000 CCD diffractometer | 3260 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2324 reflections with I > 2σ(I) |
Tmin = 0.643, Tmax = 0.883 | Rint = 0.036 |
9039 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 20 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.52 e Å−3 |
3260 reflections | Δρmin = −0.39 e Å−3 |
235 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.45163 (3) | 0.84908 (2) | 0.53293 (4) | 0.05196 (14) | |
S1 | 0.64851 (9) | 0.75144 (7) | 0.61390 (10) | 0.0399 (2) | |
S2 | 0.53469 (9) | 0.54976 (7) | 0.84635 (10) | 0.0417 (2) | |
N1 | 0.7171 (3) | 0.4450 (2) | 1.0205 (3) | 0.0387 (7) | |
C1 | 0.7338 (4) | 0.8664 (3) | 0.8361 (4) | 0.0468 (10) | |
H1 | 0.6460 | 0.8852 | 0.8067 | 0.056* | |
C2 | 0.8310 (5) | 0.9029 (3) | 0.9523 (5) | 0.0631 (13) | |
H2 | 0.8090 | 0.9470 | 1.0010 | 0.076* | |
C3 | 0.9602 (5) | 0.8738 (4) | 0.9955 (5) | 0.0705 (15) | |
H3 | 1.0252 | 0.8978 | 1.0742 | 0.085* | |
C4 | 0.9941 (5) | 0.8106 (4) | 0.9249 (5) | 0.0676 (14) | |
H4 | 1.0819 | 0.7917 | 0.9552 | 0.081* | |
C5 | 0.8988 (4) | 0.7742 (3) | 0.8080 (5) | 0.0547 (12) | |
H5 | 0.9224 | 0.7314 | 0.7591 | 0.066* | |
C6 | 0.7680 (4) | 0.8016 (3) | 0.7641 (4) | 0.0378 (9) | |
C7 | 0.6099 (4) | 0.6395 (2) | 0.6714 (4) | 0.0400 (9) | |
H7A | 0.5524 | 0.6015 | 0.5961 | 0.048* | |
H7B | 0.6910 | 0.6038 | 0.7196 | 0.048* | |
C8 | 0.5423 (4) | 0.6561 (3) | 0.7597 (4) | 0.0395 (9) | |
H8A | 0.4530 | 0.6791 | 0.7065 | 0.047* | |
H8B | 0.5899 | 0.7054 | 0.8234 | 0.047* | |
C9 | 0.7006 (3) | 0.5297 (3) | 0.9609 (4) | 0.0340 (8) | |
C10 | 0.8042 (4) | 0.5935 (3) | 0.9924 (4) | 0.0415 (9) | |
H10 | 0.7903 | 0.6522 | 0.9499 | 0.050* | |
C11 | 0.9274 (4) | 0.5689 (3) | 1.0873 (4) | 0.0477 (10) | |
H11 | 0.9986 | 0.6104 | 1.1096 | 0.057* | |
C12 | 0.9441 (4) | 0.4824 (3) | 1.1486 (4) | 0.0538 (12) | |
H12 | 1.0269 | 0.4643 | 1.2134 | 0.065* | |
C13 | 0.8382 (4) | 0.4229 (3) | 1.1139 (4) | 0.0512 (11) | |
H13 | 0.8503 | 0.3644 | 1.1568 | 0.061* | |
B1 | 0.3003 (4) | 0.6556 (3) | 0.3231 (5) | 0.0583 (14) | |
F1 | 0.3003 (14) | 0.6990 (7) | 0.4299 (11) | 0.094 (4) | 0.50 |
F2 | 0.2505 (17) | 0.5690 (7) | 0.3170 (17) | 0.092 (5) | 0.50 |
F3 | 0.2307 (13) | 0.7049 (9) | 0.2108 (11) | 0.142 (5) | 0.50 |
F4 | 0.4300 (8) | 0.6424 (14) | 0.3504 (15) | 0.079 (4) | 0.50 |
F1' | 0.3067 (17) | 0.6649 (16) | 0.4465 (11) | 0.206 (10) | 0.50 |
F2' | 0.2330 (17) | 0.5794 (9) | 0.2627 (19) | 0.128 (8) | 0.50 |
F3' | 0.2272 (18) | 0.7320 (8) | 0.2665 (15) | 0.186 (8) | 0.50 |
F4' | 0.4205 (12) | 0.6613 (17) | 0.325 (2) | 0.120 (7) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.04092 (19) | 0.04044 (19) | 0.0611 (2) | 0.01091 (14) | 0.01030 (15) | −0.00511 (16) |
S1 | 0.0404 (5) | 0.0400 (5) | 0.0383 (6) | 0.0081 (4) | 0.0165 (4) | 0.0050 (4) |
S2 | 0.0331 (5) | 0.0371 (5) | 0.0484 (6) | −0.0049 (4) | 0.0123 (4) | 0.0019 (5) |
N1 | 0.0353 (17) | 0.0369 (17) | 0.043 (2) | −0.0024 (14) | 0.0160 (15) | 0.0037 (15) |
C1 | 0.047 (2) | 0.039 (2) | 0.049 (3) | 0.0034 (18) | 0.017 (2) | 0.0021 (19) |
C2 | 0.069 (3) | 0.057 (3) | 0.057 (3) | −0.011 (2) | 0.022 (3) | −0.013 (2) |
C3 | 0.055 (3) | 0.083 (4) | 0.054 (3) | −0.024 (3) | 0.006 (3) | −0.002 (3) |
C4 | 0.038 (2) | 0.090 (4) | 0.065 (4) | −0.003 (2) | 0.013 (2) | 0.010 (3) |
C5 | 0.040 (2) | 0.064 (3) | 0.059 (3) | 0.005 (2) | 0.022 (2) | 0.010 (2) |
C6 | 0.038 (2) | 0.036 (2) | 0.038 (2) | 0.0000 (16) | 0.0151 (17) | 0.0089 (17) |
C7 | 0.045 (2) | 0.033 (2) | 0.038 (2) | 0.0061 (17) | 0.0143 (17) | −0.0003 (17) |
C8 | 0.041 (2) | 0.0324 (19) | 0.043 (2) | 0.0039 (16) | 0.0169 (17) | 0.0022 (17) |
C9 | 0.0348 (19) | 0.037 (2) | 0.034 (2) | −0.0022 (15) | 0.0188 (16) | −0.0047 (16) |
C10 | 0.042 (2) | 0.037 (2) | 0.045 (2) | −0.0058 (17) | 0.0192 (19) | 0.0003 (18) |
C11 | 0.038 (2) | 0.053 (3) | 0.050 (3) | −0.0117 (19) | 0.0173 (19) | −0.008 (2) |
C12 | 0.034 (2) | 0.058 (3) | 0.057 (3) | −0.0011 (19) | 0.010 (2) | 0.005 (2) |
C13 | 0.046 (2) | 0.046 (2) | 0.057 (3) | 0.0049 (19) | 0.018 (2) | 0.013 (2) |
B1 | 0.051 (3) | 0.057 (3) | 0.061 (4) | −0.008 (3) | 0.020 (3) | −0.009 (3) |
F1 | 0.078 (6) | 0.077 (4) | 0.128 (8) | −0.026 (4) | 0.048 (5) | −0.075 (5) |
F2 | 0.085 (9) | 0.032 (4) | 0.162 (14) | −0.021 (4) | 0.057 (9) | −0.012 (5) |
F3 | 0.136 (7) | 0.135 (8) | 0.098 (6) | 0.006 (6) | 0.000 (5) | 0.038 (6) |
F4 | 0.040 (5) | 0.118 (11) | 0.071 (5) | −0.001 (5) | 0.018 (4) | −0.029 (7) |
F1' | 0.082 (9) | 0.43 (3) | 0.101 (10) | −0.017 (14) | 0.039 (7) | −0.012 (13) |
F2' | 0.045 (5) | 0.129 (12) | 0.174 (15) | −0.022 (7) | 0.015 (8) | −0.101 (10) |
F3' | 0.254 (15) | 0.085 (7) | 0.24 (2) | 0.097 (9) | 0.127 (15) | 0.022 (9) |
F4' | 0.098 (10) | 0.111 (9) | 0.179 (17) | −0.043 (8) | 0.085 (11) | 0.003 (9) |
Ag1—N1i | 2.181 (3) | C7—H7A | 0.9700 |
Ag1—S1 | 2.4127 (11) | C7—H7B | 0.9700 |
S1—C6 | 1.780 (4) | C8—H8A | 0.9700 |
S1—C7 | 1.821 (4) | C8—H8B | 0.9700 |
S2—C9 | 1.763 (4) | C9—C10 | 1.384 (5) |
S2—C8 | 1.805 (4) | C10—C11 | 1.370 (5) |
N1—C9 | 1.336 (5) | C10—H10 | 0.9300 |
N1—C13 | 1.340 (5) | C11—C12 | 1.367 (6) |
N1—Ag1ii | 2.181 (3) | C11—H11 | 0.9300 |
C1—C6 | 1.382 (6) | C12—C13 | 1.362 (6) |
C1—C2 | 1.384 (6) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.375 (7) | B1—F2' | 1.312 (9) |
C2—H2 | 0.9300 | B1—F2 | 1.325 (8) |
C3—C4 | 1.355 (8) | B1—F3' | 1.329 (8) |
C3—H3 | 0.9300 | B1—F4' | 1.343 (9) |
C4—C5 | 1.380 (7) | B1—F3 | 1.351 (8) |
C4—H4 | 0.9300 | B1—F1 | 1.353 (8) |
C5—C6 | 1.384 (5) | B1—F4 | 1.364 (8) |
C5—H5 | 0.9300 | B1—F1' | 1.372 (9) |
C7—C8 | 1.517 (5) | ||
N1i—Ag1—S1 | 174.02 (9) | C11—C10—C9 | 119.0 (4) |
C6—S1—C7 | 101.37 (18) | C11—C10—H10 | 120.5 |
C6—S1—Ag1 | 108.55 (13) | C9—C10—H10 | 120.5 |
C7—S1—Ag1 | 107.39 (13) | C12—C11—C10 | 119.0 (4) |
C9—S2—C8 | 103.99 (18) | C12—C11—H11 | 120.5 |
C9—N1—C13 | 118.0 (3) | C10—C11—H11 | 120.5 |
C9—N1—Ag1ii | 119.8 (2) | C13—C12—C11 | 119.3 (4) |
C13—N1—Ag1ii | 122.2 (3) | C13—C12—H12 | 120.4 |
C6—C1—C2 | 119.6 (4) | C11—C12—H12 | 120.4 |
C6—C1—H1 | 120.2 | N1—C13—C12 | 122.8 (4) |
C2—C1—H1 | 120.2 | N1—C13—H13 | 118.6 |
C3—C2—C1 | 119.7 (5) | C12—C13—H13 | 118.6 |
C3—C2—H2 | 120.2 | F2'—B1—F2 | 25.2 (14) |
C1—C2—H2 | 120.2 | F2'—B1—F3' | 108.1 (12) |
C4—C3—C2 | 120.9 (5) | F2—B1—F3' | 123.6 (12) |
C4—C3—H3 | 119.6 | F2'—B1—F4' | 113.7 (14) |
C2—C3—H3 | 119.6 | F2—B1—F4' | 117.0 (14) |
C3—C4—C5 | 120.3 (5) | F3'—B1—F4' | 111.4 (14) |
C3—C4—H4 | 119.9 | F2'—B1—F3 | 87.9 (11) |
C5—C4—H4 | 119.9 | F2—B1—F3 | 111.2 (10) |
C4—C5—C6 | 119.6 (5) | F3'—B1—F3 | 32.5 (8) |
C4—C5—H5 | 120.2 | F4'—B1—F3 | 98.5 (12) |
C6—C5—H5 | 120.2 | F2'—B1—F1 | 127.0 (12) |
C1—C6—C5 | 120.0 (4) | F2—B1—F1 | 106.9 (10) |
C1—C6—S1 | 122.1 (3) | F3'—B1—F1 | 79.9 (8) |
C5—C6—S1 | 117.9 (3) | F4'—B1—F1 | 110.8 (12) |
C8—C7—S1 | 111.8 (3) | F3—B1—F1 | 112.5 (9) |
C8—C7—H7A | 109.3 | F2'—B1—F4 | 108.7 (12) |
S1—C7—H7A | 109.3 | F2—B1—F4 | 105.8 (12) |
C8—C7—H7B | 109.3 | F3'—B1—F4 | 126.3 (13) |
S1—C7—H7B | 109.3 | F4'—B1—F4 | 15.6 (18) |
H7A—C7—H7B | 107.9 | F3—B1—F4 | 113.6 (11) |
C7—C8—S2 | 112.9 (3) | F1—B1—F4 | 106.4 (9) |
C7—C8—H8A | 109.0 | F2'—B1—F1' | 111.4 (13) |
S2—C8—H8A | 109.0 | F2—B1—F1' | 88.3 (12) |
C7—C8—H8B | 109.0 | F3'—B1—F1' | 99.1 (12) |
S2—C8—H8B | 109.0 | F4'—B1—F1' | 112.1 (13) |
H8A—C8—H8B | 107.8 | F3—B1—F1' | 131.1 (12) |
N1—C9—C10 | 122.0 (3) | F1—B1—F1' | 21.4 (12) |
N1—C9—S2 | 112.2 (3) | F4—B1—F1' | 102.3 (10) |
C10—C9—S2 | 125.7 (3) | ||
N1i—Ag1—S1—C6 | −10.2 (9) | S1—C7—C8—S2 | −167.5 (2) |
N1i—Ag1—S1—C7 | 98.7 (8) | C9—S2—C8—C7 | 69.7 (3) |
C6—C1—C2—C3 | −0.6 (7) | C13—N1—C9—C10 | 0.5 (6) |
C1—C2—C3—C4 | 0.9 (8) | Ag1ii—N1—C9—C10 | 179.2 (3) |
C2—C3—C4—C5 | −0.2 (9) | C13—N1—C9—S2 | −177.3 (3) |
C3—C4—C5—C6 | −0.8 (8) | Ag1ii—N1—C9—S2 | 1.4 (4) |
C2—C1—C6—C5 | −0.3 (6) | C8—S2—C9—N1 | −170.2 (3) |
C2—C1—C6—S1 | 179.9 (3) | C8—S2—C9—C10 | 12.1 (4) |
C4—C5—C6—C1 | 1.0 (6) | N1—C9—C10—C11 | 0.2 (6) |
C4—C5—C6—S1 | −179.2 (4) | S2—C9—C10—C11 | 177.7 (3) |
C7—S1—C6—C1 | −95.3 (3) | C9—C10—C11—C12 | −0.5 (6) |
Ag1—S1—C6—C1 | 17.6 (4) | C10—C11—C12—C13 | 0.1 (7) |
C7—S1—C6—C5 | 85.0 (3) | C9—N1—C13—C12 | −0.9 (6) |
Ag1—S1—C6—C5 | −162.1 (3) | Ag1ii—N1—C13—C12 | −179.6 (3) |
C6—S1—C7—C8 | 65.6 (3) | C11—C12—C13—N1 | 0.6 (7) |
Ag1—S1—C7—C8 | −48.2 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C13H13NS2)]BF4 |
Mr | 442.04 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.252 (3), 13.999 (4), 11.315 (3) |
β (°) | 116.227 (4) |
V (Å3) | 1598.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.56 |
Crystal size (mm) | 0.16 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.643, 0.883 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9039, 3260, 2324 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.088, 0.99 |
No. of reflections | 3260 |
No. of parameters | 235 |
No. of restraints | 20 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.39 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
Ag1—N1i | 2.181 (3) | Ag1—S1 | 2.4127 (11) |
N1i—Ag1—S1 | 174.02 (9) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
There are many silver(I) complexes with substituted bisthioether compounds featuring unusual coordination motifs (Hong et al., 2000) in which donor atoms have always been the same. We report here the structure of the silver tetrafluoroborate complex, (I), of AgBF4 with the N/S-donor ligand 1-phenylsulfanyl-2-(2-pyridylsulfanyl)ethane (L).
In (I), The AgI atom exists in a nearly linear geometry (Fig. 1) which comprises a pyridyl N-atom donor and a phenylsulfanyl S-atom donor from different L molecules. The bond dimensions are within the range reported in similar complexes (Wang et al., 1992; Constable et al., 1998; Hou et al., 2004). The BF4− anion shows weak interaction with AgI center with an Ag1···F1 distance of 2.630 (9) Å, which is longer than the sum of ionic radii (2.31 Å; Shannon & Prewitt, 1969). This interaction causes a small distortion of the linear coordination of the AgI atom [S1—Ag1—N1i = 174.02 (9)°].
In the ligand, the phenyl and pyridyl rings are inclined with respect to each other at an angle of 73.1 (2)° and the S1···S2 non-bonded distance is 4.417 (2) Å. Each ligand bridges two adjacent Ag atoms through Ag—N and Ag—S coordination to give rise to an infinite chain running along the b axis. In the crystal packing of (I), adjacent chains are potentially linked into a two-dimensional network (Fig. 2) through weak Ag···S interactions [Ag1···S2(x, 3/2 − y, −1/2 + z) = S2···Ag1(x, 3/2 − y, 1/2 + z) = 3.013 (1) Å; Suenaga et al., 1999]. The anions are found between the layers.