The title compound, {[Ag
2(C
16H
16S
2)
2(C
2H
3N)
4](C
8F
4O
4)·2C
8H
2F
4O
4·4C
2H
3N}
n, has been prepared from the reaction of 2,11-dithia[3.3]paracyclophane (dtpcp) and
in situ silver(I) tetrafluoroterephthalate (TFTP
2−) using an interface method. In the solid state the title compound forms two infinite chains, which are parallel to one another. One chain consists of [Ag
2(C
16H
16S
2)
2(C
2H
3N)
4]
n2n+, and the other is formed from TFTP
2− and H
2TFTP
via O
c—H
O
c (
c is carboxy) hydrogen- bonding interactions, with H
A distances of 1.72 (2) and 1.774 (19) Å. The Ag
I ion is tetrahedrally coordinated by two acetonitrile N atoms and two dtpcp S atoms. The cyclophanes have inversion symmetry.
Supporting information
CCDC reference: 252944
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.073
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.791 0.898
Tmin' and Tmax expected: 0.895 0.898
RR' = 0.884
Please check that your absorption correction is appropriate.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1895.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 16
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C35
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.97
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C21 - C24 ... 1.53 Ang.
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C72 H60 Ag2 F12 N8 O12 S4
Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku Corporation, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000); program(s) used to solve structure: SIR88 (Burla et al., 1989); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: reference?; software used to prepare material for publication: TEXSAN.
Crystal data top
[Ag2(C16H16S2)2(C2H3N)4](C8F4O4)(C8H2F4O4)2·4C2H3N | Z = 1 |
Mr = 1801.27 | F(000) = 910.0 |
Triclinic, P1 | Dx = 1.578 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 7.416 (3) Å | Cell parameters from 6117 reflections |
b = 14.319 (6) Å | θ = 3.1–27.5° |
c = 18.883 (7) Å | µ = 0.72 mm−1 |
α = 101.449 (9)° | T = 150 K |
β = 93.00 (1)° | Block, colorless |
γ = 104.107 (8)° | 0.15 × 0.15 × 0.15 mm |
V = 1895 (1) Å3 | |
Data collection top
Rigaku/MSC Mercury CCD diffractometer | 7115 reflections with I > 2σ(I) |
Detector resolution: 14.62 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −9→9 |
Tmin = 0.791, Tmax = 0.898 | k = −18→18 |
14697 measured reflections | l = −22→24 |
8279 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0337P)2 + 0.5618P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.033 | (Δ/σ)max = 0.002 |
wR(F2) = 0.073 | Δρmax = 0.45 e Å−3 |
S = 1.03 | Δρmin = −0.41 e Å−3 |
7115 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
554 parameters | Extinction coefficient: 0.0000 |
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 | |
Ag1 | 0.89734 (2) | 0.88560 (1) | 0.73868 (1) | 0.02487 (6) | |
S1 | 0.70919 (8) | 0.88346 (4) | 0.62367 (3) | 0.0229 (1) | |
S2 | 0.76734 (8) | 0.90639 (4) | 0.86139 (3) | 0.0255 (1) | |
F1 | 0.7373 (2) | 0.4084 (1) | 0.92778 (7) | 0.0477 (4) | |
F2 | 0.7459 (2) | 0.4291 (1) | 1.07092 (7) | 0.0440 (4) | |
F3 | 0.3363 (2) | 0.6364 (1) | 0.59276 (7) | 0.0367 (3) | |
F4 | 0.3334 (2) | 0.6474 (1) | 0.45470 (7) | 0.0377 (3) | |
F5 | 0.9529 (2) | 0.6173 (1) | 0.45551 (7) | 0.0400 (4) | |
F6 | 0.9521 (2) | 0.5990 (1) | 0.59252 (7) | 0.0387 (4) | |
O1 | 0.6479 (2) | 0.5122 (1) | 0.81935 (8) | 0.0353 (4) | |
O2 | 0.3393 (2) | 0.4425 (1) | 0.80475 (8) | 0.0283 (3) | |
O3 | 0.5859 (2) | 0.6720 (1) | 0.71939 (8) | 0.0316 (4) | |
O4 | 0.6992 (2) | 0.5389 (1) | 0.69133 (8) | 0.0265 (3) | |
O5 | 0.5726 (3) | 0.7016 (1) | 0.35098 (9) | 0.0402 (4) | |
O6 | 0.7035 (2) | 0.5745 (1) | 0.33161 (8) | 0.0275 (4) | |
N1 | 1.1530 (3) | 1.0276 (2) | 0.7584 (1) | 0.0393 (5) | |
N2 | 1.0607 (3) | 0.7677 (2) | 0.7394 (1) | 0.0322 (4) | |
N3 | 0.7972 (4) | 0.7575 (3) | 1.0445 (2) | 0.0765 (9) | |
N4 | 0.7664 (5) | 1.1639 (2) | 0.7505 (2) | 0.0666 (8) | |
C1 | 0.7808 (3) | 1.0125 (2) | 0.5271 (1) | 0.0201 (4) | |
C2 | 0.8066 (3) | 1.1097 (2) | 0.5200 (1) | 0.0230 (4) | |
C3 | 0.7259 (3) | 1.1318 (2) | 0.4597 (1) | 0.0248 (5) | |
C4 | 0.6150 (3) | 1.0565 (2) | 0.4047 (1) | 0.0226 (4) | |
C5 | 0.6021 (3) | 0.9592 (2) | 0.4087 (1) | 0.0228 (4) | |
C6 | 0.6853 (3) | 0.9374 (2) | 0.4687 (1) | 0.0220 (4) | |
C7 | 0.8535 (3) | 0.9910 (2) | 0.5965 (1) | 0.0237 (5) | |
C8 | 0.5009 (3) | 0.9214 (2) | 0.6547 (1) | 0.0263 (5) | |
C9 | 0.4089 (3) | 0.8735 (2) | 0.9063 (1) | 0.0262 (5) | |
C10 | 0.4243 (3) | 0.8250 (2) | 0.9622 (1) | 0.0301 (5) | |
C11 | 0.3501 (3) | 0.8510 (2) | 1.0268 (1) | 0.0276 (5) | |
C12 | 0.2593 (3) | 0.9261 (2) | 1.0372 (1) | 0.0222 (4) | |
C13 | 0.2322 (3) | 0.9689 (2) | 0.9793 (1) | 0.0237 (5) | |
C14 | 0.3063 (3) | 0.9430 (2) | 0.9145 (1) | 0.0260 (5) | |
C15 | 0.5140 (3) | 0.8587 (2) | 0.8404 (1) | 0.0348 (6) | |
C16 | 0.8035 (4) | 1.0396 (2) | 0.8896 (1) | 0.0280 (5) | |
C17 | 1.2281 (4) | 1.1083 (2) | 0.7731 (1) | 0.0305 (5) | |
C18 | 1.3237 (5) | 1.2122 (2) | 0.7925 (2) | 0.0524 (8) | |
C19 | 1.1005 (3) | 0.6979 (2) | 0.7463 (1) | 0.0246 (5) | |
C20 | 1.1488 (3) | 0.6083 (2) | 0.7549 (1) | 0.0314 (5) | |
C21 | 0.4954 (3) | 0.4895 (2) | 0.9235 (1) | 0.0213 (4) | |
C22 | 0.6199 (3) | 0.4554 (2) | 0.9624 (1) | 0.0266 (5) | |
C23 | 0.6234 (3) | 0.4663 (2) | 1.0372 (1) | 0.0257 (5) | |
C24 | 0.4932 (3) | 0.4802 (2) | 0.8414 (1) | 0.0230 (5) | |
C25 | 0.6447 (3) | 0.6181 (1) | 0.5976 (1) | 0.0185 (4) | |
C26 | 0.4918 (3) | 0.6318 (2) | 0.5601 (1) | 0.0213 (4) | |
C27 | 0.4903 (3) | 0.6385 (2) | 0.4881 (1) | 0.0221 (4) | |
C28 | 0.6434 (3) | 0.6333 (2) | 0.4504 (1) | 0.0200 (4) | |
C29 | 0.7975 (3) | 0.6203 (2) | 0.4881 (1) | 0.0238 (5) | |
C30 | 0.7977 (3) | 0.6116 (2) | 0.5595 (1) | 0.0222 (4) | |
C31 | 0.6407 (3) | 0.6129 (2) | 0.6768 (1) | 0.0223 (4) | |
C32 | 0.6366 (3) | 0.6412 (2) | 0.3720 (1) | 0.0240 (5) | |
C33 | 0.8582 (4) | 0.7331 (2) | 0.9925 (2) | 0.0479 (7) | |
C34 | 0.9328 (4) | 0.7044 (2) | 0.9246 (2) | 0.0488 (7) | |
C35 | 0.8098 (4) | 1.2426 (2) | 0.7438 (2) | 0.0425 (6) | |
C36 | 0.8660 (5) | 1.3434 (2) | 0.7357 (2) | 0.0644 (10) | |
H1 | 0.872 (3) | 1.164 (2) | 0.559 (1) | 0.0357* | |
H2 | 0.737 (3) | 1.202 (2) | 0.456 (1) | 0.0357* | |
H3 | 0.537 (3) | 0.909 (2) | 0.373 (1) | 0.0357* | |
H4 | 0.672 (3) | 0.872 (2) | 0.471 (1) | 0.0357* | |
H5 | 0.868 (3) | 1.047 (2) | 0.635 (1) | 0.0357* | |
H6 | 0.976 (4) | 0.975 (2) | 0.592 (1) | 0.0357* | |
H7 | 0.546 (3) | 0.978 (2) | 0.692 (1) | 0.0357* | |
H8 | 0.438 (3) | 0.864 (2) | 0.671 (1) | 0.0357* | |
H9 | 0.493 (4) | 0.780 (2) | 0.957 (1) | 0.0357* | |
H10 | 0.369 (3) | 0.820 (2) | 1.066 (1) | 0.0357* | |
H11 | 0.174 (3) | 1.021 (2) | 0.984 (1) | 0.0357* | |
H12 | 0.299 (3) | 0.977 (2) | 0.876 (1) | 0.0357* | |
H13 | 0.497 (4) | 0.791 (2) | 0.822 (1) | 0.0357* | |
H14 | 0.473 (4) | 0.891 (2) | 0.803 (1) | 0.0357* | |
H15 | 0.944 (4) | 1.066 (2) | 0.890 (1) | 0.0357* | |
H16 | 0.744 (4) | 1.063 (2) | 0.853 (1) | 0.0357* | |
H17 | 1.2460 | 1.2479 | 0.8193 | 0.0638* | |
H18 | 1.3498 | 1.2362 | 0.7491 | 0.0638* | |
H19 | 1.4389 | 1.2214 | 0.8219 | 0.0638* | |
H20 | 1.2802 | 0.6230 | 0.7701 | 0.0378* | |
H21 | 1.1195 | 0.5609 | 0.7095 | 0.0378* | |
H22 | 1.0789 | 0.5816 | 0.7910 | 0.0378* | |
H23 | 0.678 (4) | 0.530 (2) | 0.733 (1) | 0.0357* | |
H24 | 0.680 (4) | 0.571 (2) | 0.291 (1) | 0.0357* | |
H25 | 1.0156 | 0.7612 | 0.9135 | 0.0582* | |
H26 | 0.8320 | 0.6768 | 0.8864 | 0.0582* | |
H27 | 1.0002 | 0.6561 | 0.9289 | 0.0582* | |
H28 | 0.7922 | 1.3811 | 0.7630 | 0.0774* | |
H29 | 0.8476 | 1.3450 | 0.6852 | 0.0774* | |
H30 | 0.9958 | 1.3712 | 0.7533 | 0.0774* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0262 (1) | 0.0289 (1) | 0.02203 (9) | 0.01137 (7) | 0.00509 (7) | 0.00561 (7) |
S1 | 0.0255 (3) | 0.0227 (3) | 0.0220 (3) | 0.0073 (2) | 0.0021 (2) | 0.0067 (2) |
S2 | 0.0242 (3) | 0.0278 (3) | 0.0220 (3) | 0.0053 (2) | 0.0080 (2) | 0.0003 (2) |
F1 | 0.065 (1) | 0.075 (1) | 0.0226 (7) | 0.0507 (9) | 0.0129 (7) | 0.0129 (7) |
F2 | 0.0608 (10) | 0.066 (1) | 0.0213 (7) | 0.0433 (9) | 0.0009 (7) | 0.0138 (7) |
F3 | 0.0257 (7) | 0.0598 (10) | 0.0335 (8) | 0.0222 (7) | 0.0150 (6) | 0.0142 (7) |
F4 | 0.0335 (8) | 0.0581 (10) | 0.0309 (8) | 0.0281 (7) | 0.0016 (6) | 0.0117 (7) |
F5 | 0.0205 (7) | 0.080 (1) | 0.0200 (7) | 0.0131 (7) | 0.0085 (5) | 0.0091 (7) |
F6 | 0.0205 (7) | 0.080 (1) | 0.0190 (7) | 0.0196 (7) | 0.0010 (5) | 0.0098 (7) |
O1 | 0.039 (1) | 0.045 (1) | 0.0175 (8) | −0.0002 (8) | 0.0032 (7) | 0.0104 (7) |
O2 | 0.0369 (9) | 0.0316 (9) | 0.0132 (7) | 0.0060 (7) | −0.0025 (7) | 0.0023 (6) |
O3 | 0.0387 (10) | 0.0312 (9) | 0.0224 (8) | 0.0079 (8) | 0.0124 (7) | −0.0007 (7) |
O4 | 0.0344 (9) | 0.0296 (9) | 0.0176 (8) | 0.0087 (7) | 0.0066 (7) | 0.0081 (7) |
O5 | 0.071 (1) | 0.0320 (10) | 0.0261 (9) | 0.0244 (9) | 0.0084 (9) | 0.0117 (7) |
O6 | 0.0353 (9) | 0.0354 (9) | 0.0131 (7) | 0.0143 (7) | 0.0014 (7) | 0.0024 (7) |
N1 | 0.039 (1) | 0.036 (1) | 0.040 (1) | 0.002 (1) | 0.003 (1) | 0.012 (1) |
N2 | 0.029 (1) | 0.030 (1) | 0.038 (1) | 0.0123 (9) | 0.0006 (9) | 0.0025 (9) |
N3 | 0.063 (2) | 0.107 (3) | 0.054 (2) | 0.009 (2) | 0.018 (2) | 0.017 (2) |
N4 | 0.104 (2) | 0.040 (2) | 0.051 (2) | 0.013 (2) | −0.013 (2) | 0.010 (1) |
C1 | 0.016 (1) | 0.026 (1) | 0.020 (1) | 0.0073 (9) | 0.0064 (8) | 0.0057 (8) |
C2 | 0.020 (1) | 0.022 (1) | 0.025 (1) | 0.0038 (9) | 0.0033 (9) | 0.0043 (9) |
C3 | 0.022 (1) | 0.025 (1) | 0.029 (1) | 0.0055 (9) | 0.0074 (9) | 0.0109 (9) |
C4 | 0.019 (1) | 0.032 (1) | 0.019 (1) | 0.0063 (9) | 0.0073 (8) | 0.0087 (9) |
C5 | 0.022 (1) | 0.026 (1) | 0.019 (1) | 0.0070 (10) | 0.0064 (9) | 0.0021 (9) |
C6 | 0.022 (1) | 0.022 (1) | 0.023 (1) | 0.0064 (9) | 0.0087 (9) | 0.0049 (9) |
C7 | 0.024 (1) | 0.024 (1) | 0.023 (1) | 0.0044 (10) | 0.0019 (9) | 0.0065 (9) |
C8 | 0.024 (1) | 0.034 (1) | 0.024 (1) | 0.007 (1) | 0.0063 (9) | 0.0107 (10) |
C9 | 0.018 (1) | 0.029 (1) | 0.021 (1) | −0.0036 (9) | 0.0047 (9) | −0.0060 (9) |
C10 | 0.027 (1) | 0.022 (1) | 0.039 (1) | 0.006 (1) | 0.010 (1) | 0.001 (1) |
C11 | 0.029 (1) | 0.023 (1) | 0.031 (1) | 0.0036 (10) | 0.008 (1) | 0.0097 (10) |
C12 | 0.021 (1) | 0.020 (1) | 0.021 (1) | −0.0005 (9) | 0.0049 (9) | 0.0023 (8) |
C13 | 0.020 (1) | 0.027 (1) | 0.022 (1) | 0.0048 (9) | 0.0018 (9) | 0.0025 (9) |
C14 | 0.021 (1) | 0.034 (1) | 0.018 (1) | 0.0003 (10) | 0.0005 (9) | 0.0037 (9) |
C15 | 0.027 (1) | 0.041 (2) | 0.025 (1) | 0.000 (1) | 0.008 (1) | −0.008 (1) |
C16 | 0.034 (1) | 0.028 (1) | 0.022 (1) | 0.006 (1) | 0.010 (1) | 0.0055 (9) |
C17 | 0.034 (1) | 0.034 (1) | 0.028 (1) | 0.009 (1) | 0.009 (1) | 0.016 (1) |
C18 | 0.076 (2) | 0.032 (1) | 0.047 (2) | 0.003 (1) | 0.022 (2) | 0.013 (1) |
C19 | 0.020 (1) | 0.028 (1) | 0.023 (1) | 0.0060 (10) | −0.0009 (9) | 0.0022 (9) |
C20 | 0.030 (1) | 0.030 (1) | 0.038 (1) | 0.012 (1) | 0.002 (1) | 0.011 (1) |
C21 | 0.031 (1) | 0.020 (1) | 0.0117 (9) | 0.0029 (9) | 0.0005 (8) | 0.0048 (8) |
C22 | 0.037 (1) | 0.029 (1) | 0.017 (1) | 0.015 (1) | 0.0057 (9) | 0.0044 (9) |
C23 | 0.035 (1) | 0.027 (1) | 0.018 (1) | 0.012 (1) | −0.0017 (9) | 0.0085 (9) |
C24 | 0.039 (1) | 0.019 (1) | 0.0126 (10) | 0.0089 (10) | 0.0023 (9) | 0.0055 (8) |
C25 | 0.020 (1) | 0.0164 (10) | 0.0169 (10) | 0.0015 (8) | 0.0037 (8) | 0.0028 (8) |
C26 | 0.020 (1) | 0.020 (1) | 0.024 (1) | 0.0065 (9) | 0.0093 (9) | 0.0039 (8) |
C27 | 0.022 (1) | 0.022 (1) | 0.024 (1) | 0.0091 (9) | −0.0005 (9) | 0.0029 (8) |
C28 | 0.025 (1) | 0.017 (1) | 0.0157 (10) | 0.0022 (9) | 0.0015 (8) | 0.0015 (8) |
C29 | 0.016 (1) | 0.033 (1) | 0.019 (1) | 0.0020 (9) | 0.0077 (8) | 0.0027 (9) |
C30 | 0.017 (1) | 0.031 (1) | 0.017 (1) | 0.0048 (9) | 0.0012 (8) | 0.0024 (9) |
C31 | 0.019 (1) | 0.024 (1) | 0.020 (1) | −0.0012 (9) | 0.0040 (9) | 0.0021 (9) |
C32 | 0.028 (1) | 0.023 (1) | 0.018 (1) | 0.0025 (10) | 0.0006 (9) | 0.0033 (9) |
C33 | 0.038 (2) | 0.046 (2) | 0.056 (2) | −0.001 (1) | 0.008 (1) | 0.015 (1) |
C34 | 0.038 (2) | 0.040 (2) | 0.061 (2) | 0.005 (1) | 0.010 (1) | −0.002 (1) |
C35 | 0.045 (2) | 0.040 (2) | 0.043 (2) | 0.014 (1) | −0.001 (1) | 0.007 (1) |
C36 | 0.048 (2) | 0.044 (2) | 0.108 (3) | 0.011 (2) | 0.023 (2) | 0.030 (2) |
Geometric parameters (Å, º) top
Ag1—S1 | 2.5099 (7) | C21—C23iii | 1.372 (3) |
Ag1—S2 | 2.5471 (6) | C21—C24 | 1.528 (3) |
Ag1—N1 | 2.369 (2) | C22—C23 | 1.388 (3) |
Ag1—N2 | 2.306 (2) | C25—C26 | 1.380 (3) |
S1—C7 | 1.829 (2) | C25—C30 | 1.387 (3) |
S1—C8 | 1.844 (3) | C25—C31 | 1.514 (3) |
S2—C15 | 1.828 (3) | C26—C27 | 1.381 (3) |
S2—C16 | 1.824 (2) | C27—C28 | 1.381 (3) |
F1—C22 | 1.345 (3) | C28—C29 | 1.385 (3) |
F2—C23 | 1.350 (3) | C28—C32 | 1.507 (3) |
F3—C26 | 1.345 (3) | C29—C30 | 1.379 (3) |
F4—C27 | 1.341 (3) | C33—C34 | 1.447 (4) |
F5—C29 | 1.340 (3) | C35—C36 | 1.444 (4) |
F6—C30 | 1.343 (3) | O4—H23 | 0.84 (2) |
O1—C24 | 1.252 (3) | O6—H24 | 0.77 (2) |
O2—C24 | 1.242 (3) | C2—H1 | 0.97 (2) |
O3—C31 | 1.209 (3) | C3—H2 | 1.01 (3) |
O4—C31 | 1.308 (3) | C5—H3 | 0.90 (2) |
O5—C32 | 1.202 (3) | C6—H4 | 0.93 (3) |
O6—C32 | 1.312 (3) | C7—H5 | 0.95 (2) |
N1—C17 | 1.125 (3) | C7—H6 | 0.99 (3) |
N2—C19 | 1.139 (4) | C8—H7 | 0.94 (2) |
N3—C33 | 1.131 (5) | C8—H8 | 0.96 (3) |
N4—C35 | 1.128 (4) | C10—H9 | 0.91 (3) |
C1—C2 | 1.391 (3) | C11—H10 | 0.96 (2) |
C1—C6 | 1.397 (3) | C13—H11 | 0.94 (3) |
C1—C7 | 1.508 (3) | C14—H12 | 0.96 (2) |
C2—C3 | 1.386 (4) | C15—H13 | 0.94 (3) |
C3—C4 | 1.396 (3) | C15—H14 | 0.99 (2) |
C4—C5 | 1.391 (4) | C16—H15 | 1.02 (3) |
C4—C8i | 1.506 (4) | C16—H16 | 0.96 (2) |
C5—C6 | 1.386 (3) | C18—H17 | 0.960 |
C9—C10 | 1.388 (4) | C18—H18 | 0.960 |
C9—C14 | 1.383 (4) | C18—H19 | 0.960 |
C9—C15 | 1.510 (3) | C20—H20 | 0.960 |
C10—C11 | 1.385 (4) | C20—H21 | 0.960 |
C11—C12 | 1.391 (4) | C20—H22 | 0.960 |
C12—C13 | 1.383 (3) | C34—H25 | 0.960 |
C12—C16ii | 1.510 (3) | C34—H26 | 0.960 |
C13—C14 | 1.388 (3) | C34—H27 | 0.960 |
C17—C18 | 1.446 (4) | C36—H28 | 0.960 |
C19—C20 | 1.450 (4) | C36—H29 | 0.960 |
C21—C22 | 1.387 (4) | C36—H30 | 0.960 |
| | | |
Ag1···S1 | 2.5099 (7) | O3···O6vi | 3.568 (2) |
Ag1···S2 | 2.5471 (6) | O4···O6vi | 2.994 (2) |
F2···C34iv | 3.406 (4) | O4···C32vi | 3.101 (2) |
F2···C20iv | 3.513 (3) | O4···O5vi | 3.452 (2) |
F3···F6v | 2.768 (2) | O4···C36viii | 3.546 (4) |
F3···C20v | 3.484 (3) | O5···C18x | 3.247 (4) |
F3···C19v | 3.537 (3) | O6···C31vi | 3.192 (3) |
F3···O6vi | 3.545 (2) | O6···C20vii | 3.257 (3) |
F3···C29vi | 3.558 (3) | O6···C24vi | 3.368 (3) |
F4···F5v | 2.750 (2) | O6···C36x | 3.518 (4) |
F4···O4vi | 3.387 (2) | N2···C15xi | 3.584 (3) |
F4···C30vi | 3.549 (3) | N3···C18xii | 3.227 (4) |
F4···F6vi | 3.555 (2) | N3···C16xii | 3.570 (4) |
F5···F6vii | 3.307 (2) | C1···C1x | 3.538 (4) |
O1···C36viii | 3.408 (4) | C10···C34v | 3.598 (4) |
O1···O6vi | 3.563 (2) | C11···C34v | 3.509 (3) |
O2···O6vi | 2.533 (2) | C11···C33v | 3.591 (4) |
O2···C18ix | 3.233 (4) | C12···C33v | 3.464 (3) |
O2···C20v | 3.301 (3) | C15···C19v | 3.497 (3) |
O2···C32vi | 3.344 (3) | C25···C27vi | 3.577 (3) |
O2···O5vi | 3.432 (2) | O1···H23 | 1.71 (3) |
O2···C36ix | 3.520 (4) | O2···H24vi | 1.77 (3) |
O3···C20v | 3.289 (3) | | |
| | | |
S1—Ag1—S2 | 122.13 (3) | O3—C31—O4 | 126.3 (2) |
S1—Ag1—N1 | 106.50 (6) | O3—C31—C25 | 121.1 (2) |
S1—Ag1—N2 | 119.17 (5) | O4—C31—C25 | 112.6 (2) |
S2—Ag1—N1 | 101.35 (6) | O5—C32—O6 | 126.0 (2) |
S2—Ag1—N2 | 104.74 (6) | O5—C32—C28 | 121.9 (2) |
N1—Ag1—N2 | 99.01 (8) | O6—C32—C28 | 112.0 (2) |
Ag1—S1—C7 | 100.67 (7) | N3—C33—C34 | 177.7 (4) |
Ag1—S1—C8 | 104.31 (8) | N4—C35—C36 | 179.7 (3) |
C7—S1—C8 | 105.1 (1) | C31—O4—H23 | 112 (2) |
Ag1—S2—C15 | 105.09 (8) | C32—O6—H24 | 112 (2) |
Ag1—S2—C16 | 103.14 (8) | C1—C2—H1 | 120 (1) |
C15—S2—C16 | 104.2 (1) | C3—C2—H1 | 117 (1) |
Ag1—N1—C17 | 157.5 (2) | C2—C3—H2 | 121 (1) |
Ag1—N2—C19 | 162.3 (2) | C4—C3—H2 | 118 (1) |
C2—C1—C6 | 118.1 (2) | C4—C5—H3 | 120 (1) |
C2—C1—C7 | 120.0 (2) | C6—C5—H3 | 118 (1) |
C6—C1—C7 | 122.0 (2) | C1—C6—H4 | 119 (1) |
C1—C2—C3 | 121.1 (2) | C5—C6—H4 | 119 (1) |
C2—C3—C4 | 120.5 (2) | S1—C7—H5 | 108 (1) |
C3—C4—C5 | 118.4 (2) | S1—C7—H6 | 103 (1) |
C3—C4—C8i | 121.5 (2) | C1—C7—H5 | 109 (1) |
C5—C4—C8i | 119.9 (2) | C1—C7—H6 | 111 (1) |
C4—C5—C6 | 120.8 (2) | H5—C7—H6 | 109 (2) |
C1—C6—C5 | 120.7 (2) | S1—C8—H7 | 105 (1) |
S1—C7—C1 | 115.4 (1) | S1—C8—H8 | 100 (1) |
S1—C8—C4i | 113.2 (2) | H7—C8—H8 | 114 (1) |
C10—C9—C14 | 118.5 (2) | C4i—C8—H7 | 110 (1) |
C10—C9—C15 | 121.7 (2) | C4i—C8—H8 | 112 (1) |
C14—C9—C15 | 119.5 (2) | C9—C10—H9 | 118 (1) |
C9—C10—C11 | 120.5 (2) | C11—C10—H9 | 120 (1) |
C10—C11—C12 | 120.8 (2) | C10—C11—H10 | 119 (1) |
C11—C12—C13 | 118.2 (2) | C12—C11—H10 | 119 (1) |
C11—C12—C16ii | 120.1 (2) | C12—C13—H11 | 121 (1) |
C13—C12—C16ii | 121.7 (2) | C14—C13—H11 | 117 (1) |
C12—C13—C14 | 120.9 (2) | C9—C14—H12 | 117 (1) |
C9—C14—C13 | 120.7 (2) | C13—C14—H12 | 121 (1) |
S2—C15—C9 | 113.2 (2) | S2—C15—H13 | 103 (1) |
S2—C16—C12ii | 114.7 (2) | S2—C15—H14 | 108 (1) |
N1—C17—C18 | 179.6 (3) | C9—C15—H13 | 109 (1) |
N2—C19—C20 | 179.3 (2) | C9—C15—H14 | 110 (1) |
C22—C21—C23iii | 116.4 (2) | H13—C15—H14 | 111 (1) |
C22—C21—C24 | 121.8 (2) | S2—C16—H15 | 103 (1) |
C23iii—C21—C24 | 121.8 (2) | S2—C16—H16 | 109 (1) |
F1—C22—C21 | 120.3 (2) | H15—C16—H16 | 108 (2) |
F1—C22—C23 | 118.5 (2) | C12ii—C16—H15 | 111 (1) |
C21—C22—C23 | 121.3 (2) | C12ii—C16—H16 | 110 (1) |
F2—C23—C21iii | 120.0 (2) | C17—C18—H17 | 109.5 |
F2—C23—C22 | 117.7 (2) | C17—C18—H18 | 109.5 |
C21iii—C23—C22 | 122.3 (2) | C17—C18—H19 | 109.5 |
O1—C24—O2 | 127.9 (2) | H17—C18—H18 | 109.5 |
O1—C24—C21 | 115.6 (2) | H17—C18—H19 | 109.5 |
O2—C24—C21 | 116.5 (2) | H18—C18—H19 | 109.5 |
C26—C25—C30 | 116.8 (2) | C19—C20—H20 | 109.5 |
C26—C25—C31 | 119.8 (2) | C19—C20—H21 | 109.5 |
C30—C25—C31 | 123.4 (2) | C19—C20—H22 | 109.5 |
F3—C26—C25 | 120.3 (2) | H20—C20—H21 | 109.5 |
F3—C26—C27 | 117.9 (2) | H20—C20—H22 | 109.5 |
C25—C26—C27 | 121.8 (2) | H21—C20—H22 | 109.5 |
F4—C27—C26 | 118.1 (2) | C33—C34—H25 | 109.5 |
F4—C27—C28 | 120.3 (2) | C33—C34—H26 | 109.5 |
C26—C27—C28 | 121.5 (2) | C33—C34—H27 | 109.5 |
C27—C28—C29 | 116.7 (2) | H25—C34—H26 | 109.5 |
C27—C28—C32 | 119.9 (2) | H25—C34—H27 | 109.5 |
C29—C28—C32 | 123.3 (2) | H26—C34—H27 | 109.5 |
F5—C29—C28 | 120.0 (2) | C35—C36—H28 | 109.5 |
F5—C29—C30 | 118.2 (2) | C35—C36—H29 | 109.5 |
C28—C29—C30 | 121.8 (2) | C35—C36—H30 | 109.5 |
F6—C30—C25 | 120.2 (2) | H28—C36—H29 | 109.5 |
F6—C30—C29 | 118.4 (2) | H28—C36—H30 | 109.5 |
C25—C30—C29 | 121.4 (2) | H29—C36—H30 | 109.5 |
| | | |
Ag1—S1—C7—C1 | 179.8 (2) | C10—C9—C14—C13 | 4.8 (3) |
Ag1—S1—C8—C4i | 169.3 (1) | C10—C11—C12—C13 | 4.9 (3) |
Ag1—S2—C15—C9 | −174.5 (2) | C10—C11—C12—C16ii | −173.9 (2) |
Ag1—S2—C16—C12ii | −179.0 (2) | C11—C10—C9—C14 | −4.7 (3) |
S1—Ag1—S2—C15 | 26.7 (1) | C11—C10—C9—C15 | 170.0 (2) |
S1—Ag1—S2—C16 | −82.22 (9) | C11—C12—C13—C14 | −4.9 (3) |
S1—Ag1—N1—C17 | 72.8 (6) | C12—C16ii—S2ii—C15ii | −71.4 (2) |
S1—Ag1—N2—C19 | −94.7 (6) | C13—C14—C9—C15 | −170.0 (2) |
S1—C7—C1—C2 | 144.9 (2) | C14—C13—C12—C16ii | 173.9 (2) |
S1—C7—C1—C6 | −34.5 (3) | C22—C23—C21iii—C24iii | 178.5 (2) |
S1—C8—C4i—C3i | 73.5 (2) | C23—C22—C21—C24 | 178.5 (2) |
S1—C8—C4i—C5i | −101.5 (2) | C25—C26—C27—C28 | −1.0 (3) |
S2—Ag1—S1—C7 | 118.55 (8) | C25—C30—C29—C28 | −1.7 (3) |
S2—Ag1—S1—C8 | 9.81 (9) | C26—C25—C30—C29 | 1.2 (3) |
S2—Ag1—N1—C17 | −55.9 (6) | C26—C27—C28—C29 | 0.5 (3) |
S2—Ag1—N2—C19 | 46.3 (6) | C26—C27—C28—C32 | −179.8 (2) |
S2—C15—C9—C10 | −66.7 (3) | C27—C26—C25—C30 | 0.1 (3) |
S2—C15—C9—C14 | 108.0 (2) | C27—C26—C25—C31 | 179.0 (2) |
S2—C16—C12ii—C11ii | −139.5 (2) | C27—C28—C29—C30 | 0.8 (3) |
S2—C16—C12ii—C13ii | 39.3 (3) | C29—C30—C25—C31 | −177.7 (2) |
F1—C22—C21—C23iii | 178.0 (2) | C30—C29—C28—C32 | −178.9 (2) |
F1—C22—C21—C24 | −3.2 (3) | O3—C31—O4—H23 | 10 (2) |
F1—C22—C23—F2 | 0.2 (3) | O5—C32—O6—H24 | −11 (2) |
F1—C22—C23—C21iii | −178.0 (2) | C1—C2—C3—H2 | 175 (1) |
F2—C23—C21iii—C22iii | −178.5 (2) | C1—C6—C5—H3 | −177 (1) |
F2—C23—C21iii—C24iii | 0.3 (3) | C2—C1—C6—H4 | 176 (1) |
F2—C23—C22—C21 | 178.5 (2) | C2—C1—C7—H5 | 22 (1) |
F3—C26—C25—C30 | 178.4 (2) | C2—C1—C7—H6 | −98 (1) |
F3—C26—C25—C31 | −2.7 (3) | C3—C4—C5—H3 | −176 (1) |
F3—C26—C27—F4 | −1.2 (3) | C3—C4—C8i—H7i | 168 (1) |
F3—C26—C27—C28 | −179.3 (2) | C3—C4—C8i—H8i | 39 (1) |
F4—C27—C26—C25 | 177.1 (2) | C4—C3—C2—H1 | −174 (1) |
F4—C27—C28—C29 | −177.6 (2) | C4—C5—C6—H4 | 178 (1) |
F4—C27—C28—C32 | 2.1 (3) | C5—C4—C3—H2 | 178 (1) |
F5—C29—C28—C27 | −178.2 (2) | C5—C4—C8i—H7i | −16 (1) |
F5—C29—C28—C32 | 2.1 (3) | C5—C4—C8i—H8i | −145 (1) |
F5—C29—C30—F6 | −1.1 (3) | C6—C1—C2—H1 | −179 (1) |
F5—C29—C30—C25 | 177.3 (2) | C6—C1—C7—H5 | −157 (1) |
F6—C30—C25—C26 | 179.5 (2) | C6—C1—C7—H6 | 82 (1) |
F6—C30—C25—C31 | 0.7 (3) | C7—S1—C8—H7 | −57 (1) |
F6—C30—C29—C28 | 179.9 (2) | C7—S1—C8—H8 | −176 (1) |
O1—C24—C21—C22 | −51.6 (3) | C7—C1—C2—H1 | 0 (1) |
O1—C24—C21—C23iii | 127.2 (2) | C7—C1—C6—H4 | −4 (1) |
O2—C24—C21—C22 | 128.8 (2) | C8—S1—C7—H5 | 51 (1) |
O2—C24—C21—C23iii | −52.5 (3) | C8—S1—C7—H6 | 166 (1) |
O3—C31—C25—C26 | −46.1 (3) | C8—C4i—C3i—H2i | 6 (1) |
O3—C31—C25—C30 | 132.7 (2) | C8—C4i—C5i—H3i | −8 (1) |
O4—C31—C25—C26 | 133.1 (2) | C9—C10—C11—H10 | −175 (1) |
O4—C31—C25—C30 | −48.1 (2) | C9—C14—C13—H11 | 174 (1) |
O5—C32—C28—C27 | 43.6 (3) | C10—C9—C14—H12 | 178 (1) |
O5—C32—C28—C29 | −136.7 (2) | C10—C9—C15—H13 | 48 (1) |
O6—C32—C28—C27 | −135.0 (2) | C10—C9—C15—H14 | 171 (1) |
O6—C32—C28—C29 | 44.8 (3) | C11—C12—C13—H11 | −178 (1) |
N1—Ag1—S1—C7 | 3.2 (1) | C11—C12—C16ii—H15ii | −104 (1) |
N1—Ag1—S1—C8 | −105.6 (1) | C11—C12—C16ii—H16ii | 15 (1) |
N1—Ag1—S2—C15 | 144.6 (1) | C12—C11—C10—H9 | 174 (2) |
N1—Ag1—S2—C16 | 35.7 (1) | C12—C13—C14—H12 | −173 (1) |
N1—Ag1—N2—C19 | 150.6 (6) | C13—C12—C11—H10 | −179 (1) |
N2—Ag1—S1—C7 | −107.5 (1) | C13—C12—C16ii—H15ii | 77 (1) |
N2—Ag1—S1—C8 | 143.80 (10) | C13—C12—C16ii—H16ii | −163 (1) |
N2—Ag1—S2—C15 | −112.8 (1) | C14—C9—C10—H9 | −179 (2) |
N2—Ag1—S2—C16 | 138.29 (10) | C14—C9—C15—H13 | −136 (1) |
N2—Ag1—N1—C17 | −163.0 (6) | C14—C9—C15—H14 | −13 (1) |
C1—C2—C3—C4 | 0.6 (4) | C15—S2—C16—H15 | −167 (1) |
C1—C6—C5—C4 | 1.3 (3) | C15—S2—C16—H16 | −53 (1) |
C1—C7—S1—C8 | −72.1 (2) | C15—C9—C10—H9 | −5 (2) |
C2—C1—C6—C5 | −6.6 (3) | C15—C9—C14—H12 | 3 (1) |
C2—C3—C4—C5 | −5.9 (3) | C16—S2—C15—H13 | 175 (1) |
C2—C3—C4—C8i | 169.2 (2) | C16—S2—C15—H14 | 56 (1) |
C3—C2—C1—C6 | 5.6 (3) | C16—C12ii—C11ii—H10ii | −1 (1) |
C3—C2—C1—C7 | −173.8 (2) | C16—C12ii—C13ii—H11ii | 0 (1) |
C3—C4—C5—C6 | 4.9 (3) | C25—C31—O4—H23 | −169 (2) |
C4—C8i—S1i—C7i | −63.8 (2) | C28—C32—O6—H24 | 167 (2) |
C5—C6—C1—C7 | 172.8 (2) | H1—C2—C3—H2 | 1 (2) |
C6—C5—C4—C8i | −170.3 (2) | H9—C10—C11—H10 | −2 (3) |
C9—C10—C11—C12 | −0.1 (3) | H9—C10—C11—H10 | −2 (3) |
C9—C14—C13—C12 | 0.1 (3) | H9—C10—C11—H10 | −2 (3) |
C9—C15—S2—C16 | −66.3 (2) | | |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+2; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) −x+2, −y+1, −z+1; (viii) x, y−1, z; (ix) x−1, y−1, z; (x) −x+2, −y+2, −z+1; (xi) x+1, y, z; (xii) −x+2, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H23···O1 | 0.84 (2) | 1.71 (3) | 2.555 (2) | 177 (3) |
O6vi—H24vi···O2 | 0.77 (2) | 1.77 (3) | 2.533 (2) | 171 (4) |
Symmetry code: (vi) −x+1, −y+1, −z+1. |