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The title compound, {[Ag(C
16H
16S
2)(C
2H
3N)
2](C
6HF
8O
4)}
n, forms two infinite chains, which are approximately perpendicular to each other. One chain consists of [Ag(C
16H
16S
2)(C
2H
3N)
2]
nn+, and the other is formed from HOFA
− (HOFA
− is hydrogen octafluoroadipate) units
via O
c—H
O
c (c is carboxy) hydrogen-bonding interactions, with an H
A distance of 1.66 (5) Å. Each silver(I) cation lies on a crystallographic twofold rotation axis and has a tetrahedral geometry, defined by two N atoms belonging to two acetonitrile molecules and two S atoms from two 2,11-dithia[3.3]paracyclophane molecules. The cyclophanes have inversion symmetry.
Supporting information
CCDC reference: 242288
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.067
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.78 Ratio
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C12
Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 8
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... N1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear; cell refinement: CrystalClear; data reduction: TEXSAN Ver. 1.11 (TEXSAN, 1999); program(s) used to solve structure: SIR88 (Burla et al., 1989); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN Ver. 1.11; software used to prepare material for publication: TEXSAN Ver. 1.11.
Crystal data top
[Ag(C16H16S2)(C2H3N)2](C6HF8O4) | F(000) = 1504.0 |
Mr = 751.45 | Dx = 1.702 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 4112 reflections |
a = 8.748 (1) Å | θ = 3.2–27.5° |
b = 19.503 (2) Å | µ = 0.91 mm−1 |
c = 17.247 (2) Å | T = 150 K |
β = 94.842 (5)° | Block, colourless |
V = 2932.2 (6) Å3 | 0.20 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Rigaku/MSC Mercury CCD diffractometer | 2847 reflections with I > 2σ(I) |
Detector resolution: 14.62 pixels mm-1 | Rint = 0.032 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −10→11 |
Tmin = 0.778, Tmax = 0.872 | k = −25→24 |
11413 measured reflections | l = −22→19 |
3352 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0252P)2 + 2.7139P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = −0.001 |
wR(F2) = 0.067 | Δρmax = 0.34 e Å−3 |
S = 1.10 | Δρmin = −0.36 e Å−3 |
2847 reflections | Extinction correction: SHELXL97 |
223 parameters | Extinction coefficient: none |
H atoms treated by a mixture of independent and constrained refinement | |
Special details top
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ag1 | 1.0000 | 0.45636 (1) | 0.7500 | 0.0327 (1) | |
S1 | 0.77210 (6) | 0.49623 (3) | 0.66707 (3) | 0.0240 (1) | |
F1 | 0.7320 (2) | 0.72386 (9) | 0.78062 (8) | 0.0421 (4) | |
F2 | 0.8006 (2) | 0.61744 (8) | 0.80364 (8) | 0.0469 (4) | |
F3 | 1.0345 (2) | 0.76246 (7) | 0.82251 (7) | 0.0324 (3) | |
F4 | 1.0958 (2) | 0.65452 (8) | 0.82779 (8) | 0.0357 (4) | |
O1 | 0.7551 (2) | 0.7447 (1) | 0.92958 (9) | 0.0347 (4) | |
O2 | 0.8954 (2) | 0.6496 (1) | 0.9523 (1) | 0.0389 (4) | |
N1 | 0.9114 (4) | 0.3708 (1) | 0.8316 (2) | 0.0637 (8) | |
C1 | 0.5153 (2) | 0.4280 (1) | 0.6012 (1) | 0.0221 (5) | |
C2 | 0.5003 (3) | 0.3967 (1) | 0.5293 (1) | 0.0275 (5) | |
C3 | 0.3821 (3) | 0.4144 (1) | 0.4742 (1) | 0.0286 (5) | |
C4 | 0.2769 (2) | 0.4643 (1) | 0.4899 (1) | 0.0211 (5) | |
C5 | 0.2855 (3) | 0.4921 (1) | 0.5640 (1) | 0.0272 (5) | |
C6 | 0.4033 (3) | 0.4738 (1) | 0.6191 (1) | 0.0299 (6) | |
C7 | 0.6592 (3) | 0.4170 (1) | 0.6548 (2) | 0.0265 (5) | |
C8 | 0.8431 (3) | 0.5097 (1) | 0.5716 (1) | 0.0245 (5) | |
C9 | 0.8299 (3) | 0.6926 (1) | 0.9106 (1) | 0.0256 (5) | |
C10 | 0.8348 (3) | 0.6836 (1) | 0.8217 (1) | 0.0263 (5) | |
C11 | 0.9938 (3) | 0.6999 (1) | 0.7946 (1) | 0.0218 (5) | |
C12 | 0.8942 (3) | 0.3270 (2) | 0.8709 (2) | 0.0392 (6) | |
C13 | 0.8718 (4) | 0.2711 (2) | 0.9223 (2) | 0.080 (1) | |
H1 | 0.570 (4) | 0.366 (1) | 0.516 (2) | 0.0499* | |
H2 | 0.380 (3) | 0.395 (1) | 0.424 (2) | 0.0499* | |
H3 | 0.215 (3) | 0.526 (2) | 0.575 (2) | 0.0499* | |
H4 | 0.409 (3) | 0.495 (1) | 0.668 (2) | 0.0499* | |
H5 | 0.720 (3) | 0.383 (2) | 0.636 (2) | 0.0499* | |
H6 | 0.637 (3) | 0.409 (1) | 0.710 (2) | 0.0499* | |
H7 | 0.889 (3) | 0.468 (2) | 0.555 (2) | 0.0499* | |
H8 | 0.923 (3) | 0.544 (2) | 0.582 (2) | 0.0499* | |
H9 | 0.7666 | 0.2567 | 0.9159 | 0.0983* | |
H10 | 0.8967 | 0.2855 | 0.9750 | 0.0983* | |
H11 | 0.9371 | 0.2336 | 0.9104 | 0.0983* | |
H12 | 0.757 (9) | 0.749 (4) | 0.975 (3) | 0.0499* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0303 (2) | 0.0310 (2) | 0.0331 (2) | 0.0000 | −0.0191 (1) | 0.0000 |
S1 | 0.0226 (3) | 0.0246 (3) | 0.0229 (3) | 0.0008 (2) | −0.0100 (2) | −0.0012 (2) |
F1 | 0.0281 (8) | 0.074 (1) | 0.0237 (7) | 0.0098 (8) | −0.0002 (6) | −0.0009 (7) |
F2 | 0.070 (1) | 0.0433 (9) | 0.0303 (8) | −0.0323 (8) | 0.0198 (8) | −0.0157 (7) |
F3 | 0.0406 (8) | 0.0312 (8) | 0.0258 (7) | −0.0121 (7) | 0.0048 (6) | −0.0094 (6) |
F4 | 0.0405 (9) | 0.0460 (9) | 0.0213 (7) | 0.0182 (7) | 0.0064 (6) | 0.0108 (6) |
O1 | 0.048 (1) | 0.035 (1) | 0.0227 (9) | 0.0017 (9) | 0.0123 (9) | −0.0059 (9) |
O2 | 0.049 (1) | 0.044 (1) | 0.0239 (9) | 0.0084 (9) | 0.0061 (8) | −0.0008 (8) |
N1 | 0.074 (2) | 0.044 (2) | 0.072 (2) | −0.008 (1) | 0.002 (2) | 0.019 (2) |
C1 | 0.019 (1) | 0.022 (1) | 0.024 (1) | −0.0049 (9) | −0.0036 (9) | 0.0065 (9) |
C2 | 0.029 (1) | 0.020 (1) | 0.032 (1) | 0.0048 (10) | −0.007 (1) | 0.000 (1) |
C3 | 0.033 (1) | 0.023 (1) | 0.027 (1) | 0.004 (1) | −0.010 (1) | −0.006 (1) |
C4 | 0.018 (1) | 0.020 (1) | 0.024 (1) | −0.0047 (9) | −0.0056 (8) | 0.0021 (9) |
C5 | 0.019 (1) | 0.036 (1) | 0.027 (1) | 0.003 (1) | 0.0013 (9) | −0.003 (1) |
C6 | 0.026 (1) | 0.043 (2) | 0.020 (1) | 0.001 (1) | −0.0007 (10) | −0.003 (1) |
C7 | 0.024 (1) | 0.024 (1) | 0.029 (1) | −0.0010 (10) | −0.0088 (10) | 0.004 (1) |
C8 | 0.018 (1) | 0.025 (1) | 0.029 (1) | 0.0017 (10) | −0.0065 (9) | 0.000 (1) |
C9 | 0.028 (1) | 0.031 (1) | 0.019 (1) | −0.008 (1) | 0.0071 (9) | −0.005 (1) |
C10 | 0.030 (1) | 0.029 (1) | 0.020 (1) | −0.006 (1) | 0.0048 (10) | −0.0066 (10) |
C11 | 0.027 (1) | 0.020 (1) | 0.018 (1) | −0.0004 (9) | 0.0013 (9) | −0.0014 (9) |
C12 | 0.035 (2) | 0.037 (2) | 0.046 (2) | −0.005 (1) | −0.002 (1) | 0.002 (1) |
C13 | 0.064 (2) | 0.090 (3) | 0.079 (3) | −0.042 (2) | −0.032 (2) | 0.042 (2) |
Geometric parameters (Å, º) top
Ag1—S1 | 2.4787 (5) | C4—C8ii | 1.516 (3) |
Ag1—S1i | 2.4787 (5) | C5—C6 | 1.388 (3) |
Ag1—N1 | 2.355 (3) | C9—C10 | 1.548 (3) |
Ag1—N1i | 2.355 (3) | C10—C11 | 1.537 (3) |
S1—C7 | 1.837 (3) | C11—C11i | 1.550 (4) |
S1—C8 | 1.827 (3) | C12—C13 | 1.428 (5) |
F1—C10 | 1.348 (3) | O1—H12 | 0.793 |
F2—C10 | 1.355 (3) | C2—H1 | 0.90 (3) |
F3—C11 | 1.350 (3) | C3—H2 | 0.94 (3) |
F4—C11 | 1.349 (3) | C5—H3 | 0.93 (3) |
O1—C9 | 1.266 (3) | C6—H4 | 0.94 (3) |
O2—C9 | 1.216 (3) | C7—H5 | 0.93 (3) |
N1—C12 | 1.109 (4) | C7—H6 | 1.00 (3) |
C1—C2 | 1.379 (3) | C8—H7 | 0.96 (4) |
C1—C6 | 1.379 (3) | C8—H8 | 0.97 (3) |
C1—C7 | 1.513 (3) | C13—H9 | 0.960 |
C2—C3 | 1.387 (3) | C13—H10 | 0.960 |
C3—C4 | 1.383 (3) | C13—H11 | 0.960 |
C4—C5 | 1.384 (3) | | |
| | | |
F1···C12iii | 3.407 (3) | O1···O2vi | 3.254 (3) |
F2···C5iv | 3.471 (3) | O1···C13vii | 3.385 (4) |
F3···C13v | 3.292 (4) | O2···C13viii | 3.236 (4) |
F3···C12v | 3.426 (3) | O2···C5iv | 3.456 (3) |
F3···C7iii | 3.496 (3) | O2···C12viii | 3.456 (3) |
F3···C1iii | 3.527 (3) | N1···C5iv | 3.511 (4) |
O1···C9vi | 3.162 (3) | N1···C6iv | 3.568 (4) |
| | | |
S1—Ag1—S1i | 143.43 (3) | F3—C11—C10 | 107.2 (2) |
S1—Ag1—N1 | 106.12 (8) | F3—C11—C11i | 108.4 (1) |
S1—Ag1—N1i | 99.61 (7) | F4—C11—C10 | 108.6 (2) |
S1i—Ag1—N1 | 99.61 (7) | F4—C11—C11i | 108.8 (2) |
S1i—Ag1—N1i | 106.12 (8) | C10—C11—C11i | 116.3 (2) |
N1—Ag1—N1i | 89.8 (1) | N1—C12—C13 | 179.4 (4) |
Ag1—S1—C7 | 101.60 (8) | C9—O1—H12 | 112.8 |
Ag1—S1—C8 | 104.30 (7) | C1—C2—H1 | 121 (2) |
C7—S1—C8 | 103.7 (1) | C3—C2—H1 | 118 (2) |
Ag1—N1—C12 | 168.4 (3) | C2—C3—H2 | 119 (1) |
C2—C1—C6 | 118.2 (2) | C4—C3—H2 | 120 (1) |
C2—C1—C7 | 119.8 (2) | C4—C5—H3 | 119 (2) |
C6—C1—C7 | 121.7 (2) | C6—C5—H3 | 121 (2) |
C1—C2—C3 | 120.9 (2) | C1—C6—H4 | 120 (1) |
C2—C3—C4 | 120.8 (2) | C5—C6—H4 | 118 (1) |
C3—C4—C5 | 118.1 (2) | S1—C7—H5 | 109 (2) |
C3—C4—C8ii | 122.1 (2) | S1—C7—H6 | 99 (1) |
C5—C4—C8ii | 119.7 (2) | C1—C7—H5 | 111 (2) |
C4—C5—C6 | 120.7 (2) | C1—C7—H6 | 112 (1) |
C1—C6—C5 | 120.9 (2) | H5—C7—H6 | 113 (3) |
S1—C7—C1 | 111.2 (2) | S1—C8—H7 | 109 (2) |
S1—C8—C4ii | 114.3 (2) | S1—C8—H8 | 103 (2) |
O1—C9—O2 | 128.9 (2) | C4ii—C8—H7 | 111 (2) |
O1—C9—C10 | 113.9 (2) | C4ii—C8—H8 | 110 (2) |
O2—C9—C10 | 117.2 (2) | H7—C8—H8 | 109 (3) |
F1—C10—F2 | 108.0 (2) | C12—C13—H9 | 109.5 |
F1—C10—C9 | 112.4 (2) | C12—C13—H10 | 109.5 |
F1—C10—C11 | 107.5 (2) | C12—C13—H11 | 109.5 |
F2—C10—C9 | 108.1 (2) | H9—C13—H10 | 109.5 |
F2—C10—C11 | 108.3 (2) | H9—C13—H11 | 109.5 |
C9—C10—C11 | 112.3 (2) | H10—C13—H11 | 109.5 |
F3—C11—F4 | 107.2 (2) | | |
Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1, y, −z+3/2; (v) x+1/2, y+1/2, z; (vi) −x+3/2, −y+3/2, −z+2; (vii) x−1/2, y+1/2, z; (viii) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H12···O1vi | 0.79 (5) | 1.66 (5) | 2.447 (3) | 175 (10) |
Symmetry code: (vi) −x+3/2, −y+3/2, −z+2. |
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