Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031911/wm2128sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031911/wm2128Isup2.hkl |
CCDC reference: 657538
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.012 Å
- Disorder in main residue
- R factor = 0.043
- wR factor = 0.107
- Data-to-parameter ratio = 22.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.34 From the CIF: _reflns_number_total 16990 Count of symmetry unique reflns 9442 Completeness (_total/calc) 179.94% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 7548 Fraction of Friedel pairs measured 0.799 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 327
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Background information on similar tetrameric AgI monodentate adducts is given by Bowen et al. (1994), Teo & Calabrese (1975, 1976) and Meijboom et al. (2006). Background reference on helicity is given by Eliel et al. (1994).
Synthesis of [Ag(PCyPh2)I]4: 1 equivalent of AgI and 1.1 equivalents of diphenylcyclohexylphosphine were added in vial containing anhydrous tetrahydrofuran (THF). The mixture was allowed to stir for 3 h at room temperature in darkness. Removal of THF yielded a white powder residue which was washed with several portions of pentane. Colorless crystals were grown by layering pentane over a saturated CH2Cl2 solution at room temperature in the dark (yield 50%).
Three symmetry unique phenyl groups in [Ag(PCyPh2)I]4 were located disordered each in two positions and were treated as rigid flat hexagons having C—C distances constrained to 1.39 Å with refined site occupancies of 67/33, 70/30 and 78/22, respectively, and were subjected to rigid bond restraints. Equal atomic displacement parameters were applied to chemically equivalent atoms in the disordered contributions and bond distances were restrained to be the same. An anti-bumping restraint was applied between C64, a carbon atom of a minor disordered contributor, and C39 in a cyclohexyl ring. H atoms were assigned calculated positions with Uiso restrained to be 1.2Ueq of the bonded C atom and a C—H distance of 0.95–0.99 Å. The highest peak and deepest hole in the final difference map are located 0.97 and 0.72 Å, respectively, from Ag1.
The 1:1 AgI:PCyPh2 (PCyPh2 is diphenylcyclohexylphosphine) tetrameric complex is similar to reported analogues with other monodentate phosphine ligands (Bowen et al., 1994; Teo & Calabrese, 1975 and 1976; Meijboom et al., 2006). The silver and iodine atoms alternate in a distorted cubane-like AgI core with phosphine capping the silver corners (Fig. 1). Two symmetry unique but structurally similar tetramers are each located on a twofold axis. Each face is distorted such that the average Ag···Ag atomic separation is shorter than the average I···I atomic separation by about 1 Å. A closer inspection shows that the two faces completed by the twofold axis differ from each other and from the four adjacent faces in that they display the shortest and longest I···I separations for each cubane. If the face with the shortest I···I separation is assigned to be proximal, an inspection of the cyclohexyl fragments clearly show (P) helicity (Eliel et al., 1994) for both symmetry unique molecules (Fig. 2). The starting materials do not display chirality suggesting spontaneous resolution during crystallization. We also note that the proximal and distal planes could easily be inverted by slight distortion of the cubane-like core. Alternatively, concerted rotation along the Ag—P bonds would reverse the helicity. The Flack parameter refined to a value of -0.029 (18) indicating the true hand of the data has been correctly determined.
Background information on similar tetrameric AgI monodentate adducts is given by Bowen et al. (1994), Teo & Calabrese (1975, 1976) and Meijboom et al. (2006). Background reference on helicity is given by Eliel et al. (1994).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.
[Ag4I4(C18H21P)4] | F(000) = 3904 |
Mr = 2012.35 | Dx = 1.849 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 998 reflections |
a = 24.698 (9) Å | θ = 2.4–26.6° |
b = 12.404 (5) Å | µ = 2.91 mm−1 |
c = 24.328 (9) Å | T = 120 K |
β = 104.145 (7)° | Block, colourless |
V = 7227 (5) Å3 | 0.15 × 0.14 × 0.09 mm |
Z = 4 |
Bruker APEX diffractometer | 16990 independent reflections |
Radiation source: fine-focus sealed tube | 15397 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 836.6 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ω scans | h = −32→32 |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | k = −16→16 |
Tmin = 0.652, Tmax = 0.767 | l = −31→32 |
42119 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0456P)2 + 26.0708P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
16990 reflections | Δρmax = 2.48 e Å−3 |
742 parameters | Δρmin = −1.27 e Å−3 |
327 restraints | Absolute structure: Flack (1983), 7870 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.029 (18) |
[Ag4I4(C18H21P)4] | V = 7227 (5) Å3 |
Mr = 2012.35 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 24.698 (9) Å | µ = 2.91 mm−1 |
b = 12.404 (5) Å | T = 120 K |
c = 24.328 (9) Å | 0.15 × 0.14 × 0.09 mm |
β = 104.145 (7)° |
Bruker APEX diffractometer | 16990 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 15397 reflections with I > 2σ(I) |
Tmin = 0.652, Tmax = 0.767 | Rint = 0.041 |
42119 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0456P)2 + 26.0708P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | Δρmax = 2.48 e Å−3 |
16990 reflections | Δρmin = −1.27 e Å−3 |
742 parameters | Absolute structure: Flack (1983), 7870 Friedel pairs |
327 restraints | Absolute structure parameter: −0.029 (18) |
Experimental. Data collection is performed with four batch runs at φ = 0.00 ° (600 frames), at φ = 90.00 ° (600 frames), at φ = 180 ° (600 frames) and at φ = 270 ° (600 frames). Frame width = 0.30 ° in ω. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. |
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 > 2σ(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 | 0.57326 (3) | 0.94301 (5) | 0.52831 (3) | 0.06118 (18) | |
Ag2 | 0.49338 (3) | 0.74512 (5) | 0.57164 (2) | 0.04812 (14) | |
Ag3 | 1.01975 (3) | 0.55462 (5) | 0.07637 (3) | 0.05755 (17) | |
Ag4 | 0.93112 (2) | 0.35289 (4) | 0.00325 (3) | 0.04431 (13) | |
I1 | 0.591930 (19) | 0.70934 (4) | 0.53562 (2) | 0.04137 (11) | |
I2 | 0.48125 (2) | 0.97682 (4) | 0.58617 (2) | 0.05396 (13) | |
I3 | 0.90958 (2) | 0.58414 (3) | 0.00354 (2) | 0.04997 (13) | |
I4 | 1.027377 (18) | 0.32713 (3) | 0.098437 (18) | 0.03722 (9) | |
P1 | 0.65521 (8) | 1.04838 (16) | 0.57606 (8) | 0.0425 (4) | |
P2 | 0.46790 (7) | 0.64854 (14) | 0.64952 (7) | 0.0333 (3) | |
P3 | 1.04524 (11) | 0.66022 (16) | 0.16369 (9) | 0.0521 (5) | |
P4 | 0.84888 (7) | 0.24331 (15) | 0.00446 (7) | 0.0372 (4) | |
C1 | 0.6946 (3) | 1.1312 (6) | 0.4848 (3) | 0.0504 (18) | |
H1A | 0.6815 | 1.2028 | 0.4941 | 0.060* | |
H1B | 0.6633 | 1.0954 | 0.4577 | 0.060* | |
C2 | 0.7433 (3) | 1.1453 (6) | 0.4577 (4) | 0.056 (2) | |
H2A | 0.7732 | 1.1868 | 0.4837 | 0.067* | |
H2B | 0.7309 | 1.1870 | 0.4222 | 0.067* | |
C3 | 0.7666 (4) | 1.0373 (7) | 0.4447 (4) | 0.055 (2) | |
H3A | 0.7382 | 0.9995 | 0.4152 | 0.066* | |
H3B | 0.7999 | 1.0496 | 0.4296 | 0.066* | |
C4 | 0.7824 (4) | 0.9681 (8) | 0.4965 (4) | 0.063 (2) | |
H4A | 0.8144 | 1.0010 | 0.5239 | 0.076* | |
H4B | 0.7941 | 0.8962 | 0.4860 | 0.076* | |
C5 | 0.7329 (4) | 0.9549 (6) | 0.5246 (4) | 0.055 (2) | |
H5A | 0.7024 | 0.9144 | 0.4989 | 0.066* | |
H5B | 0.7452 | 0.9131 | 0.5602 | 0.066* | |
C6 | 0.7114 (3) | 1.0649 (6) | 0.5376 (3) | 0.0465 (17) | |
H6A | 0.7431 | 1.1030 | 0.5638 | 0.056* | |
C7 | 0.7451 (7) | 1.0293 (11) | 0.6723 (6) | 0.049 (3) | 0.67 (4) |
H7A | 0.7581 | 1.0949 | 0.6599 | 0.059* | 0.67 (4) |
C8 | 0.7783 (4) | 0.9733 (16) | 0.7177 (6) | 0.065 (3) | 0.67 (4) |
H8A | 0.8140 | 1.0007 | 0.7364 | 0.078* | 0.67 (4) |
C9 | 0.7593 (8) | 0.8773 (13) | 0.7358 (6) | 0.084 (5) | 0.67 (4) |
H9A | 0.7820 | 0.8391 | 0.7668 | 0.101* | 0.67 (4) |
C10 | 0.7071 (10) | 0.8373 (14) | 0.7084 (7) | 0.091 (6) | 0.67 (4) |
H10A | 0.6942 | 0.7717 | 0.7208 | 0.109* | 0.67 (4) |
C11 | 0.6739 (7) | 0.8933 (16) | 0.6630 (7) | 0.073 (5) | 0.67 (4) |
H11A | 0.6383 | 0.8659 | 0.6443 | 0.088* | 0.67 (4) |
C12 | 0.6929 (6) | 0.9892 (11) | 0.6449 (5) | 0.048 (2) | 0.67 (4) |
C73 | 0.7553 (11) | 1.002 (3) | 0.6688 (12) | 0.049 (3) | 0.33 (4) |
H73A | 0.7789 | 1.0477 | 0.6534 | 0.059* | 0.33 (4) |
C74 | 0.7773 (10) | 0.944 (3) | 0.7179 (13) | 0.065 (3) | 0.33 (4) |
H74A | 0.8159 | 0.9494 | 0.7361 | 0.078* | 0.33 (4) |
C75 | 0.7428 (18) | 0.877 (3) | 0.7405 (12) | 0.084 (5) | 0.33 (4) |
H75A | 0.7579 | 0.8376 | 0.7741 | 0.101* | 0.33 (4) |
C76 | 0.6864 (17) | 0.869 (3) | 0.7139 (16) | 0.091 (6) | 0.33 (4) |
H76A | 0.6628 | 0.8241 | 0.7293 | 0.109* | 0.33 (4) |
C77 | 0.6644 (11) | 0.928 (3) | 0.6647 (15) | 0.073 (5) | 0.33 (4) |
H77A | 0.6258 | 0.9224 | 0.6465 | 0.088* | 0.33 (4) |
C78 | 0.6989 (12) | 0.994 (2) | 0.6422 (10) | 0.048 (2) | 0.33 (4) |
C13 | 0.6649 (4) | 1.2421 (7) | 0.6414 (4) | 0.056 (2) | |
H13A | 0.6908 | 1.2052 | 0.6707 | 0.067* | |
C14 | 0.6532 (4) | 1.3491 (7) | 0.6486 (4) | 0.056 (2) | |
H14A | 0.6694 | 1.3842 | 0.6834 | 0.068* | |
C15 | 0.6181 (4) | 1.4050 (7) | 0.6054 (4) | 0.054 (2) | |
H15A | 0.6113 | 1.4795 | 0.6097 | 0.065* | |
C16 | 0.5931 (4) | 1.3525 (7) | 0.5562 (4) | 0.058 (2) | |
H16A | 0.5688 | 1.3911 | 0.5265 | 0.069* | |
C17 | 0.6029 (4) | 1.2434 (8) | 0.5491 (4) | 0.058 (2) | |
H17A | 0.5845 | 1.2074 | 0.5152 | 0.069* | |
C18 | 0.6396 (3) | 1.1876 (6) | 0.5920 (3) | 0.0392 (15) | |
C19 | 0.5484 (3) | 0.7426 (6) | 0.7368 (4) | 0.0514 (18) | |
H19A | 0.5196 | 0.7974 | 0.7382 | 0.062* | |
H19B | 0.5691 | 0.7669 | 0.7090 | 0.062* | |
C20 | 0.5890 (4) | 0.7326 (7) | 0.7957 (4) | 0.056 (2) | |
H20A | 0.6095 | 0.8013 | 0.8054 | 0.068* | |
H20B | 0.5674 | 0.7194 | 0.8245 | 0.068* | |
C21 | 0.6300 (3) | 0.6427 (8) | 0.7976 (4) | 0.057 (2) | |
H21A | 0.6561 | 0.6628 | 0.7743 | 0.068* | |
H21B | 0.6521 | 0.6333 | 0.8372 | 0.068* | |
C22 | 0.6030 (4) | 0.5390 (7) | 0.7768 (4) | 0.059 (2) | |
H22A | 0.5817 | 0.5125 | 0.8037 | 0.071* | |
H22B | 0.6321 | 0.4850 | 0.7754 | 0.071* | |
C23 | 0.5634 (4) | 0.5501 (7) | 0.7177 (4) | 0.058 (2) | |
H23A | 0.5851 | 0.5697 | 0.6899 | 0.069* | |
H23B | 0.5448 | 0.4801 | 0.7061 | 0.069* | |
C24 | 0.5200 (3) | 0.6348 (5) | 0.7175 (3) | 0.0374 (14) | |
H24A | 0.4994 | 0.6130 | 0.7464 | 0.045* | |
C25 | 0.4719 (4) | 0.4442 (7) | 0.6074 (4) | 0.057 (2) | |
H25A | 0.5020 | 0.4733 | 0.5942 | 0.068* | |
C26 | 0.4587 (4) | 0.3355 (8) | 0.5979 (4) | 0.065 (2) | |
H26A | 0.4807 | 0.2907 | 0.5803 | 0.078* | |
C27 | 0.4141 (4) | 0.2941 (7) | 0.6140 (4) | 0.061 (2) | |
H27A | 0.4053 | 0.2197 | 0.6086 | 0.074* | |
C28 | 0.3817 (4) | 0.3604 (8) | 0.6382 (4) | 0.066 (2) | |
H28A | 0.3492 | 0.3325 | 0.6475 | 0.079* | |
C29 | 0.3963 (4) | 0.4690 (7) | 0.6492 (4) | 0.0551 (19) | |
H29A | 0.3741 | 0.5140 | 0.6665 | 0.066* | |
C30 | 0.4429 (3) | 0.5105 (6) | 0.6349 (3) | 0.0372 (14) | |
C31 | 0.3631 (3) | 0.7377 (6) | 0.6252 (3) | 0.0455 (16) | |
H31A | 0.3640 | 0.7213 | 0.5873 | 0.055* | |
C32 | 0.3156 (4) | 0.7850 (7) | 0.6361 (4) | 0.059 (2) | |
H32A | 0.2838 | 0.7973 | 0.6058 | 0.071* | |
C33 | 0.3145 (4) | 0.8136 (8) | 0.6895 (4) | 0.064 (2) | |
H33A | 0.2820 | 0.8458 | 0.6966 | 0.077* | |
C34 | 0.3611 (4) | 0.7957 (9) | 0.7339 (4) | 0.069 (3) | |
H34A | 0.3611 | 0.8182 | 0.7712 | 0.083* | |
C35 | 0.4076 (4) | 0.7448 (7) | 0.7234 (3) | 0.0533 (19) | |
H35A | 0.4389 | 0.7305 | 0.7540 | 0.064* | |
C36 | 0.4087 (3) | 0.7146 (6) | 0.6692 (3) | 0.0395 (14) | |
C37 | 0.9802 (4) | 0.5462 (6) | 0.2222 (4) | 0.070 (2) | |
H37A | 0.9652 | 0.5065 | 0.1864 | 0.084* | |
H37B | 1.0142 | 0.5083 | 0.2432 | 0.084* | |
C38 | 0.9372 (4) | 0.5445 (8) | 0.2572 (5) | 0.078 (2) | |
H38A | 0.9243 | 0.4694 | 0.2595 | 0.093* | |
H38B | 0.9551 | 0.5685 | 0.2962 | 0.093* | |
C39 | 0.8893 (4) | 0.6122 (7) | 0.2347 (5) | 0.086 (2) | |
H39A | 0.8675 | 0.6186 | 0.2637 | 0.103* | |
H39B | 0.8652 | 0.5754 | 0.2014 | 0.103* | |
C40 | 0.9015 (4) | 0.7225 (7) | 0.2172 (5) | 0.075 (2) | |
H40A | 0.9157 | 0.7670 | 0.2514 | 0.090* | |
H40B | 0.8664 | 0.7559 | 0.1952 | 0.090* | |
C41 | 0.9441 (4) | 0.7227 (7) | 0.1814 (4) | 0.070 (2) | |
H41A | 0.9268 | 0.6912 | 0.1438 | 0.083* | |
H41B | 0.9545 | 0.7981 | 0.1755 | 0.083* | |
C42 | 0.9957 (4) | 0.6603 (6) | 0.2083 (4) | 0.0654 (19) | |
H42A | 1.0140 | 0.6967 | 0.2448 | 0.078* | |
C43 | 1.0662 (4) | 0.8782 (7) | 0.1958 (4) | 0.063 (2) | |
H43A | 1.0648 | 0.8553 | 0.2327 | 0.075* | |
C44 | 1.0755 (4) | 0.9838 (8) | 0.1865 (5) | 0.074 (3) | |
H44A | 1.0797 | 1.0349 | 0.2164 | 0.089* | |
C45 | 1.0787 (4) | 1.0152 (6) | 0.1339 (6) | 0.073 (3) | |
H45A | 1.0860 | 1.0888 | 0.1276 | 0.088* | |
C46 | 1.0716 (4) | 0.9445 (7) | 0.0901 (5) | 0.075 (3) | |
H46A | 1.0735 | 0.9689 | 0.0536 | 0.090* | |
C47 | 1.0614 (4) | 0.8354 (7) | 0.0989 (4) | 0.060 (2) | |
H47A | 1.0565 | 0.7850 | 0.0687 | 0.072* | |
C48 | 1.0588 (3) | 0.8027 (5) | 0.1521 (3) | 0.0489 (18) | |
C49 | 1.1575 (14) | 0.603 (5) | 0.1732 (14) | 0.063 (3) | 0.22 (3) |
H49A | 1.1472 | 0.5995 | 0.1330 | 0.076* | 0.22 (3) |
C50 | 1.2121 (12) | 0.581 (4) | 0.203 (2) | 0.074 (4) | 0.22 (3) |
H50A | 1.2391 | 0.5624 | 0.1824 | 0.089* | 0.22 (3) |
C51 | 1.2271 (11) | 0.587 (4) | 0.261 (2) | 0.078 (4) | 0.22 (3) |
H51A | 1.2644 | 0.5716 | 0.2814 | 0.094* | 0.22 (3) |
C52 | 1.1875 (18) | 0.614 (4) | 0.2909 (15) | 0.090 (5) | 0.22 (3) |
H52A | 1.1978 | 0.6179 | 0.3311 | 0.107* | 0.22 (3) |
C53 | 1.1329 (16) | 0.636 (4) | 0.2616 (16) | 0.072 (4) | 0.22 (3) |
H53A | 1.1059 | 0.6550 | 0.2818 | 0.086* | 0.22 (3) |
C54 | 1.1179 (10) | 0.631 (5) | 0.2028 (16) | 0.058 (3) | 0.22 (3) |
C85 | 1.1550 (4) | 0.6036 (11) | 0.1920 (5) | 0.063 (3) | 0.78 (3) |
H85A | 1.1503 | 0.6061 | 0.1521 | 0.076* | 0.78 (3) |
C86 | 1.2076 (3) | 0.5856 (10) | 0.2274 (6) | 0.074 (4) | 0.78 (3) |
H86A | 1.2389 | 0.5757 | 0.2117 | 0.089* | 0.78 (3) |
C87 | 1.2144 (4) | 0.5819 (10) | 0.2858 (6) | 0.078 (4) | 0.78 (3) |
H87A | 1.2503 | 0.5696 | 0.3100 | 0.094* | 0.78 (3) |
C88 | 1.1686 (6) | 0.5964 (10) | 0.3088 (4) | 0.090 (5) | 0.78 (3) |
H88A | 1.1733 | 0.5939 | 0.3487 | 0.107* | 0.78 (3) |
C89 | 1.1160 (5) | 0.6144 (11) | 0.2734 (4) | 0.072 (4) | 0.78 (3) |
H89A | 1.0848 | 0.6243 | 0.2891 | 0.086* | 0.78 (3) |
C90 | 1.1092 (4) | 0.6181 (11) | 0.2150 (4) | 0.058 (3) | 0.78 (3) |
C55 | 0.8124 (3) | 0.1958 (6) | −0.1115 (3) | 0.0410 (15) | |
H55A | 0.8203 | 0.1186 | −0.1028 | 0.049* | |
H55B | 0.8470 | 0.2300 | −0.1165 | 0.049* | |
C56 | 0.7666 (3) | 0.2062 (6) | −0.1663 (3) | 0.055 (2) | |
H56A | 0.7800 | 0.1749 | −0.1980 | 0.066* | |
H56B | 0.7334 | 0.1646 | −0.1626 | 0.066* | |
C57 | 0.7499 (3) | 0.3227 (6) | −0.1800 (3) | 0.0526 (19) | |
H57A | 0.7815 | 0.3621 | −0.1888 | 0.063* | |
H57B | 0.7181 | 0.3253 | −0.2139 | 0.063* | |
C58 | 0.7333 (3) | 0.3771 (8) | −0.1309 (3) | 0.060 (2) | |
H58A | 0.7255 | 0.4543 | −0.1399 | 0.072* | |
H58B | 0.6988 | 0.3436 | −0.1251 | 0.072* | |
C59 | 0.7791 (3) | 0.3674 (6) | −0.0770 (3) | 0.052 (2) | |
H59A | 0.7666 | 0.4012 | −0.0454 | 0.062* | |
H59B | 0.8126 | 0.4067 | −0.0816 | 0.062* | |
C60 | 0.7944 (3) | 0.2495 (6) | −0.0624 (3) | 0.0432 (16) | |
H60A | 0.7604 | 0.2115 | −0.0568 | 0.052* | |
C61 | 0.7774 (9) | 0.2483 (14) | 0.0737 (10) | 0.057 (3) | 0.297 (12) |
H61A | 0.7689 | 0.1772 | 0.0597 | 0.069* | 0.297 (12) |
C62 | 0.7485 (9) | 0.294 (2) | 0.1103 (11) | 0.070 (4) | 0.297 (12) |
H62A | 0.7201 | 0.2534 | 0.1214 | 0.084* | 0.297 (12) |
C63 | 0.7610 (9) | 0.398 (2) | 0.1307 (9) | 0.081 (6) | 0.297 (12) |
H63A | 0.7412 | 0.4285 | 0.1557 | 0.097* | 0.297 (12) |
C64 | 0.8024 (9) | 0.4563 (17) | 0.1145 (9) | 0.070 (4) | 0.297 (12) |
H64A | 0.8110 | 0.5274 | 0.1285 | 0.084* | 0.297 (12) |
C65 | 0.8314 (8) | 0.4111 (17) | 0.0779 (9) | 0.055 (3) | 0.297 (12) |
H65A | 0.8597 | 0.4512 | 0.0668 | 0.066* | 0.297 (12) |
C66 | 0.8189 (9) | 0.3071 (17) | 0.0575 (9) | 0.036 (2) | 0.297 (12) |
C79 | 0.7599 (3) | 0.2106 (7) | 0.0582 (4) | 0.057 (3) | 0.703 (12) |
H79A | 0.7536 | 0.1440 | 0.0383 | 0.069* | 0.703 (12) |
C80 | 0.7248 (3) | 0.2428 (8) | 0.0918 (4) | 0.070 (4) | 0.703 (12) |
H80A | 0.6944 | 0.1983 | 0.0950 | 0.084* | 0.703 (12) |
C81 | 0.7341 (4) | 0.3402 (9) | 0.1209 (4) | 0.081 (6) | 0.703 (12) |
H81A | 0.7100 | 0.3622 | 0.1439 | 0.097* | 0.703 (12) |
C82 | 0.7785 (4) | 0.4053 (8) | 0.1163 (4) | 0.070 (4) | 0.703 (12) |
H82A | 0.7849 | 0.4719 | 0.1361 | 0.084* | 0.703 (12) |
C83 | 0.8137 (3) | 0.3731 (7) | 0.0826 (4) | 0.055 (3) | 0.703 (12) |
H83A | 0.8441 | 0.4176 | 0.0795 | 0.066* | 0.703 (12) |
C84 | 0.8044 (3) | 0.2757 (7) | 0.0536 (3) | 0.036 (2) | 0.703 (12) |
C67 | 0.9137 (3) | 0.0797 (5) | 0.0602 (3) | 0.0364 (13) | |
H67A | 0.9389 | 0.1365 | 0.0750 | 0.044* | |
C68 | 0.9272 (3) | −0.0280 (6) | 0.0768 (3) | 0.0462 (16) | |
H68A | 0.9617 | −0.0438 | 0.1029 | 0.055* | |
C69 | 0.8908 (4) | −0.1097 (6) | 0.0555 (3) | 0.0516 (19) | |
H69A | 0.9000 | −0.1817 | 0.0676 | 0.062* | |
C70 | 0.8409 (4) | −0.0888 (7) | 0.0167 (4) | 0.061 (2) | |
H70A | 0.8164 | −0.1459 | 0.0009 | 0.073* | |
C71 | 0.8271 (4) | 0.0183 (7) | 0.0011 (4) | 0.058 (2) | |
H71A | 0.7921 | 0.0337 | −0.0243 | 0.070* | |
C72 | 0.8630 (3) | 0.1016 (5) | 0.0216 (3) | 0.0390 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0498 (3) | 0.0511 (4) | 0.0721 (4) | −0.0034 (3) | −0.0053 (3) | 0.0026 (3) |
Ag2 | 0.0504 (3) | 0.0512 (3) | 0.0477 (3) | −0.0002 (3) | 0.0214 (3) | 0.0046 (3) |
Ag3 | 0.0764 (4) | 0.0337 (3) | 0.0575 (4) | −0.0062 (3) | 0.0067 (3) | −0.0041 (3) |
Ag4 | 0.0405 (3) | 0.0304 (3) | 0.0569 (3) | 0.0017 (2) | 0.0022 (2) | 0.0028 (2) |
I1 | 0.0359 (2) | 0.0399 (2) | 0.0495 (3) | 0.00681 (18) | 0.01294 (19) | 0.00699 (19) |
I2 | 0.0532 (3) | 0.0412 (3) | 0.0620 (3) | 0.0034 (2) | 0.0033 (2) | −0.0064 (2) |
I3 | 0.0619 (3) | 0.0273 (2) | 0.0531 (3) | 0.0066 (2) | −0.0005 (2) | −0.00548 (19) |
I4 | 0.0363 (2) | 0.02788 (19) | 0.0439 (2) | 0.00317 (16) | 0.00288 (17) | 0.00464 (17) |
P1 | 0.0396 (9) | 0.0375 (9) | 0.0478 (10) | −0.0014 (8) | 0.0057 (8) | 0.0066 (8) |
P2 | 0.0306 (8) | 0.0367 (9) | 0.0320 (8) | 0.0008 (7) | 0.0063 (6) | 0.0012 (7) |
P3 | 0.0752 (15) | 0.0266 (9) | 0.0516 (11) | −0.0001 (9) | 0.0101 (10) | −0.0013 (8) |
P4 | 0.0325 (8) | 0.0401 (9) | 0.0380 (8) | 0.0070 (7) | 0.0069 (7) | 0.0079 (7) |
C1 | 0.057 (5) | 0.041 (4) | 0.054 (4) | 0.008 (3) | 0.015 (4) | 0.011 (3) |
C2 | 0.050 (5) | 0.038 (4) | 0.082 (6) | −0.007 (3) | 0.023 (4) | 0.005 (4) |
C3 | 0.055 (5) | 0.048 (4) | 0.067 (5) | −0.003 (4) | 0.022 (4) | −0.005 (4) |
C4 | 0.067 (6) | 0.053 (5) | 0.075 (6) | 0.014 (4) | 0.027 (5) | −0.003 (5) |
C5 | 0.077 (6) | 0.034 (4) | 0.057 (5) | 0.005 (4) | 0.021 (4) | 0.006 (3) |
C6 | 0.053 (4) | 0.041 (4) | 0.048 (4) | 0.007 (3) | 0.017 (3) | 0.004 (3) |
C7 | 0.036 (6) | 0.059 (8) | 0.052 (5) | 0.021 (5) | 0.009 (4) | 0.002 (5) |
C8 | 0.064 (5) | 0.084 (10) | 0.045 (4) | 0.015 (5) | 0.008 (4) | 0.002 (6) |
C9 | 0.104 (11) | 0.102 (8) | 0.044 (6) | 0.004 (8) | 0.011 (6) | 0.022 (5) |
C10 | 0.108 (11) | 0.097 (12) | 0.060 (7) | −0.020 (9) | 0.005 (8) | 0.039 (8) |
C11 | 0.077 (7) | 0.069 (11) | 0.070 (6) | −0.008 (7) | 0.013 (5) | 0.030 (8) |
C12 | 0.039 (4) | 0.049 (4) | 0.057 (4) | 0.008 (3) | 0.015 (3) | 0.014 (3) |
C73 | 0.036 (6) | 0.059 (8) | 0.052 (5) | 0.021 (5) | 0.009 (4) | 0.002 (5) |
C74 | 0.064 (5) | 0.084 (10) | 0.045 (4) | 0.015 (5) | 0.008 (4) | 0.002 (6) |
C75 | 0.104 (11) | 0.102 (8) | 0.044 (6) | 0.004 (8) | 0.011 (6) | 0.022 (5) |
C76 | 0.108 (11) | 0.097 (12) | 0.060 (7) | −0.020 (9) | 0.005 (8) | 0.039 (8) |
C77 | 0.077 (7) | 0.069 (11) | 0.070 (6) | −0.008 (7) | 0.013 (5) | 0.030 (8) |
C78 | 0.039 (4) | 0.049 (4) | 0.057 (4) | 0.008 (3) | 0.015 (3) | 0.014 (3) |
C13 | 0.052 (5) | 0.050 (5) | 0.059 (5) | 0.011 (4) | 0.001 (4) | 0.011 (4) |
C14 | 0.058 (5) | 0.058 (5) | 0.049 (4) | 0.002 (4) | 0.005 (4) | 0.001 (4) |
C15 | 0.057 (5) | 0.047 (4) | 0.067 (5) | 0.008 (4) | 0.029 (4) | 0.001 (4) |
C16 | 0.064 (5) | 0.060 (5) | 0.053 (5) | 0.025 (4) | 0.021 (4) | 0.013 (4) |
C17 | 0.057 (5) | 0.068 (6) | 0.051 (4) | 0.018 (4) | 0.017 (4) | −0.003 (4) |
C18 | 0.039 (3) | 0.039 (4) | 0.039 (3) | 0.000 (3) | 0.008 (3) | 0.007 (3) |
C19 | 0.040 (4) | 0.038 (4) | 0.068 (5) | −0.004 (3) | −0.001 (3) | −0.003 (4) |
C20 | 0.056 (5) | 0.049 (5) | 0.055 (5) | −0.006 (4) | −0.006 (4) | −0.016 (4) |
C21 | 0.046 (4) | 0.069 (6) | 0.050 (5) | 0.006 (4) | 0.001 (3) | −0.006 (4) |
C22 | 0.061 (5) | 0.054 (5) | 0.051 (5) | 0.018 (4) | −0.007 (4) | −0.002 (4) |
C23 | 0.052 (5) | 0.053 (5) | 0.062 (5) | 0.015 (4) | 0.002 (4) | −0.007 (4) |
C24 | 0.033 (3) | 0.035 (3) | 0.040 (3) | 0.001 (3) | 0.000 (3) | −0.007 (3) |
C25 | 0.054 (5) | 0.060 (5) | 0.055 (5) | −0.020 (4) | 0.013 (4) | −0.020 (4) |
C26 | 0.071 (6) | 0.061 (5) | 0.065 (5) | −0.007 (5) | 0.021 (4) | −0.023 (5) |
C27 | 0.085 (7) | 0.046 (5) | 0.050 (4) | −0.022 (4) | 0.008 (4) | −0.013 (4) |
C28 | 0.059 (5) | 0.057 (5) | 0.079 (6) | −0.021 (4) | 0.013 (5) | −0.002 (5) |
C29 | 0.054 (5) | 0.051 (4) | 0.061 (5) | −0.006 (4) | 0.015 (4) | 0.001 (4) |
C30 | 0.035 (3) | 0.039 (3) | 0.035 (3) | −0.006 (3) | 0.003 (3) | −0.001 (3) |
C31 | 0.042 (4) | 0.048 (4) | 0.048 (4) | 0.004 (3) | 0.014 (3) | −0.002 (3) |
C32 | 0.046 (5) | 0.060 (5) | 0.068 (5) | 0.010 (4) | 0.005 (4) | 0.003 (4) |
C33 | 0.046 (5) | 0.064 (6) | 0.086 (6) | 0.011 (4) | 0.023 (4) | −0.014 (5) |
C34 | 0.071 (6) | 0.079 (7) | 0.065 (6) | 0.007 (5) | 0.030 (5) | −0.020 (5) |
C35 | 0.053 (4) | 0.055 (5) | 0.050 (4) | 0.003 (4) | 0.008 (3) | −0.007 (4) |
C36 | 0.035 (3) | 0.039 (3) | 0.047 (4) | 0.004 (3) | 0.015 (3) | 0.001 (3) |
C37 | 0.099 (5) | 0.040 (3) | 0.079 (5) | 0.006 (4) | 0.035 (4) | 0.010 (4) |
C38 | 0.103 (6) | 0.054 (4) | 0.086 (5) | 0.006 (4) | 0.042 (4) | 0.012 (4) |
C39 | 0.097 (5) | 0.068 (5) | 0.100 (6) | 0.006 (4) | 0.039 (5) | 0.017 (4) |
C40 | 0.080 (5) | 0.058 (4) | 0.085 (5) | 0.012 (4) | 0.017 (4) | 0.010 (4) |
C41 | 0.077 (5) | 0.050 (4) | 0.076 (5) | −0.001 (3) | 0.007 (4) | 0.022 (4) |
C42 | 0.087 (5) | 0.037 (3) | 0.074 (5) | 0.007 (3) | 0.024 (4) | 0.008 (3) |
C43 | 0.073 (6) | 0.039 (4) | 0.071 (6) | 0.001 (4) | 0.007 (5) | −0.012 (4) |
C44 | 0.057 (6) | 0.044 (5) | 0.108 (8) | −0.004 (4) | −0.007 (5) | −0.021 (5) |
C45 | 0.042 (5) | 0.028 (4) | 0.161 (11) | −0.002 (3) | 0.046 (6) | −0.009 (5) |
C46 | 0.089 (7) | 0.031 (4) | 0.121 (9) | 0.003 (4) | 0.057 (7) | 0.015 (5) |
C47 | 0.076 (6) | 0.034 (4) | 0.076 (6) | 0.003 (4) | 0.033 (5) | 0.003 (4) |
C48 | 0.060 (5) | 0.023 (3) | 0.060 (5) | −0.003 (3) | 0.008 (4) | −0.003 (3) |
C49 | 0.083 (6) | 0.056 (6) | 0.047 (6) | −0.008 (5) | 0.008 (5) | 0.004 (6) |
C50 | 0.083 (6) | 0.066 (6) | 0.067 (8) | 0.009 (6) | 0.007 (6) | −0.004 (7) |
C51 | 0.089 (7) | 0.065 (6) | 0.067 (8) | 0.024 (7) | −0.007 (6) | 0.004 (8) |
C52 | 0.111 (9) | 0.098 (9) | 0.045 (6) | 0.050 (9) | −0.007 (5) | 0.006 (7) |
C53 | 0.085 (7) | 0.075 (9) | 0.052 (6) | 0.010 (7) | 0.009 (5) | 0.001 (6) |
C54 | 0.083 (6) | 0.034 (5) | 0.048 (6) | 0.018 (5) | 0.000 (4) | 0.003 (5) |
C85 | 0.083 (6) | 0.056 (6) | 0.047 (6) | −0.008 (5) | 0.008 (5) | 0.004 (6) |
C86 | 0.083 (6) | 0.066 (6) | 0.067 (8) | 0.009 (6) | 0.007 (6) | −0.004 (7) |
C87 | 0.089 (7) | 0.065 (6) | 0.067 (8) | 0.024 (7) | −0.007 (6) | 0.004 (8) |
C88 | 0.111 (9) | 0.098 (9) | 0.045 (6) | 0.050 (9) | −0.007 (5) | 0.006 (7) |
C89 | 0.085 (7) | 0.075 (9) | 0.052 (6) | 0.010 (7) | 0.009 (5) | 0.001 (6) |
C90 | 0.083 (6) | 0.034 (5) | 0.048 (6) | 0.018 (5) | 0.000 (4) | 0.003 (5) |
C55 | 0.033 (3) | 0.042 (4) | 0.045 (4) | 0.000 (3) | 0.005 (3) | 0.002 (3) |
C56 | 0.053 (4) | 0.067 (5) | 0.042 (4) | −0.017 (4) | 0.006 (3) | 0.002 (4) |
C57 | 0.049 (4) | 0.067 (5) | 0.041 (4) | 0.000 (4) | 0.010 (3) | 0.019 (4) |
C58 | 0.048 (4) | 0.081 (6) | 0.052 (5) | 0.021 (4) | 0.013 (4) | 0.020 (4) |
C59 | 0.046 (4) | 0.065 (5) | 0.046 (4) | 0.018 (4) | 0.014 (3) | 0.020 (4) |
C60 | 0.028 (3) | 0.053 (4) | 0.043 (4) | 0.006 (3) | −0.001 (3) | 0.013 (3) |
C61 | 0.030 (6) | 0.084 (10) | 0.058 (7) | −0.003 (6) | 0.011 (5) | 0.016 (7) |
C62 | 0.035 (7) | 0.108 (13) | 0.070 (8) | 0.002 (6) | 0.019 (6) | 0.029 (8) |
C63 | 0.059 (9) | 0.142 (18) | 0.046 (6) | 0.025 (9) | 0.017 (7) | 0.016 (9) |
C64 | 0.049 (8) | 0.104 (13) | 0.061 (7) | 0.012 (7) | 0.021 (6) | −0.001 (8) |
C65 | 0.050 (7) | 0.063 (9) | 0.052 (6) | 0.005 (6) | 0.015 (5) | 0.010 (6) |
C66 | 0.023 (5) | 0.049 (7) | 0.034 (4) | −0.001 (4) | 0.003 (4) | 0.016 (4) |
C79 | 0.030 (6) | 0.084 (10) | 0.058 (7) | −0.003 (6) | 0.011 (5) | 0.016 (7) |
C80 | 0.035 (7) | 0.108 (13) | 0.070 (8) | 0.002 (6) | 0.019 (6) | 0.029 (8) |
C81 | 0.059 (9) | 0.142 (18) | 0.046 (6) | 0.025 (9) | 0.017 (7) | 0.016 (9) |
C82 | 0.049 (8) | 0.104 (13) | 0.061 (7) | 0.012 (7) | 0.021 (6) | −0.001 (8) |
C83 | 0.050 (7) | 0.063 (9) | 0.052 (6) | 0.005 (6) | 0.015 (5) | 0.010 (6) |
C84 | 0.023 (5) | 0.049 (7) | 0.034 (4) | −0.001 (4) | 0.003 (4) | 0.016 (4) |
C67 | 0.036 (3) | 0.032 (3) | 0.039 (3) | 0.001 (3) | 0.006 (3) | 0.003 (3) |
C68 | 0.046 (4) | 0.035 (3) | 0.053 (4) | 0.000 (3) | 0.004 (3) | 0.006 (3) |
C69 | 0.067 (5) | 0.035 (4) | 0.049 (4) | −0.008 (4) | 0.007 (4) | 0.009 (3) |
C70 | 0.077 (6) | 0.046 (5) | 0.056 (5) | −0.029 (4) | 0.010 (4) | 0.010 (4) |
C71 | 0.048 (4) | 0.062 (5) | 0.058 (5) | −0.017 (4) | −0.003 (4) | 0.017 (4) |
C72 | 0.035 (3) | 0.033 (3) | 0.047 (4) | 0.002 (3) | 0.006 (3) | 0.002 (3) |
Ag1—P1 | 2.450 (2) | C29—H29A | 0.9500 |
Ag1—I2i | 2.8129 (13) | C31—C36 | 1.382 (10) |
Ag1—I1 | 2.9334 (14) | C31—C32 | 1.392 (11) |
Ag1—I2 | 2.9808 (13) | C31—H31A | 0.9500 |
Ag2—P2 | 2.4503 (19) | C32—C33 | 1.353 (12) |
Ag2—I1 | 2.8163 (11) | C32—H32A | 0.9500 |
Ag2—I2 | 2.9199 (14) | C33—C34 | 1.391 (13) |
Ag2—I1i | 2.9595 (11) | C33—H33A | 0.9500 |
Ag3—P3 | 2.444 (2) | C34—C35 | 1.387 (12) |
Ag3—I4 | 2.8700 (13) | C34—H34A | 0.9500 |
Ag3—I3 | 2.8846 (12) | C35—C36 | 1.379 (10) |
Ag3—I3ii | 2.9355 (12) | C35—H35A | 0.9500 |
Ag4—P4 | 2.450 (2) | C37—C38 | 1.515 (10) |
Ag4—I4 | 2.9029 (10) | C37—C42 | 1.526 (9) |
Ag4—I4ii | 2.9175 (12) | C37—H37A | 0.9900 |
Ag4—I3 | 2.9176 (13) | C37—H37B | 0.9900 |
I1—Ag2i | 2.9593 (11) | C38—C39 | 1.445 (10) |
I2—Ag1i | 2.8129 (13) | C38—H38A | 0.9900 |
I3—Ag3ii | 2.9355 (12) | C38—H38B | 0.9900 |
I4—Ag4ii | 2.9176 (12) | C39—C40 | 1.486 (10) |
P1—C18 | 1.831 (7) | C39—H39A | 0.9900 |
P1—C78 | 1.831 (14) | C39—H39B | 0.9900 |
P1—C12 | 1.858 (8) | C40—C41 | 1.520 (10) |
P1—C6 | 1.865 (8) | C40—H40A | 0.9900 |
P2—C30 | 1.825 (7) | C40—H40B | 0.9900 |
P2—C36 | 1.838 (7) | C41—C42 | 1.499 (10) |
P2—C24 | 1.839 (7) | C41—H41A | 0.9900 |
P3—C42 | 1.822 (9) | C41—H41B | 0.9900 |
P3—C90 | 1.834 (6) | C42—H42A | 1.0000 |
P3—C48 | 1.834 (7) | C43—C44 | 1.358 (13) |
P3—C54 | 1.850 (16) | C43—C48 | 1.396 (11) |
P4—C66 | 1.818 (12) | C43—H43A | 0.9500 |
P4—C72 | 1.821 (7) | C44—C45 | 1.359 (16) |
P4—C60 | 1.843 (7) | C44—H44A | 0.9500 |
P4—C84 | 1.854 (5) | C45—C46 | 1.358 (15) |
C1—C6 | 1.495 (11) | C45—H45A | 0.9500 |
C1—C2 | 1.517 (11) | C46—C47 | 1.403 (11) |
C1—H1A | 0.9900 | C46—H46A | 0.9500 |
C1—H1B | 0.9900 | C47—C48 | 1.371 (12) |
C2—C3 | 1.521 (11) | C47—H47A | 0.9500 |
C2—H2A | 0.9900 | C49—C50 | 1.3900 |
C2—H2B | 0.9900 | C49—C54 | 1.3900 |
C3—C4 | 1.496 (13) | C49—H49A | 0.9500 |
C3—H3A | 0.9900 | C50—C51 | 1.3705 |
C3—H3B | 0.9900 | C50—H50A | 0.9500 |
C4—C5 | 1.549 (12) | C51—C52 | 1.3900 |
C4—H4A | 0.9900 | C51—H51A | 0.9500 |
C4—H4B | 0.9900 | C52—C53 | 1.3900 |
C5—C6 | 1.525 (10) | C52—H52A | 0.9500 |
C5—H5A | 0.9900 | C53—C54 | 1.3900 |
C5—H5B | 0.9900 | C53—H53A | 0.9500 |
C6—H6A | 1.0000 | C85—C86 | 1.3900 |
C7—C8 | 1.3900 | C85—C90 | 1.3900 |
C7—C12 | 1.3900 | C85—H85A | 0.9500 |
C7—H7A | 0.9500 | C86—C87 | 1.3900 |
C8—C9 | 1.3900 | C86—H86A | 0.9500 |
C8—H8A | 0.9500 | C87—C88 | 1.3900 |
C9—C10 | 1.3900 | C87—H87A | 0.9500 |
C9—H9A | 0.9500 | C88—C89 | 1.3900 |
C10—C11 | 1.3900 | C88—H88A | 0.9500 |
C10—H10A | 0.9500 | C89—C90 | 1.3900 |
C11—C12 | 1.3900 | C89—H89A | 0.9500 |
C11—H11A | 0.9500 | C55—C60 | 1.526 (8) |
C73—C74 | 1.3900 | C55—C56 | 1.529 (8) |
C73—C78 | 1.3900 | C55—H55A | 0.9900 |
C73—H73A | 0.9500 | C55—H55B | 0.9900 |
C74—C75 | 1.3900 | C56—C57 | 1.516 (9) |
C74—H74A | 0.9500 | C56—H56A | 0.9900 |
C75—C76 | 1.3900 | C56—H56B | 0.9900 |
C75—H75A | 0.9500 | C57—C58 | 1.513 (9) |
C76—C77 | 1.3900 | C57—H57A | 0.9900 |
C76—H76A | 0.9500 | C57—H57B | 0.9900 |
C77—C78 | 1.3900 | C58—C59 | 1.512 (9) |
C77—H77A | 0.9500 | C58—H58A | 0.9900 |
C13—C14 | 1.378 (12) | C58—H58B | 0.9900 |
C13—C18 | 1.387 (11) | C59—C60 | 1.530 (9) |
C13—H13A | 0.9500 | C59—H59A | 0.9900 |
C14—C15 | 1.374 (12) | C59—H59B | 0.9900 |
C14—H14A | 0.9500 | C60—H60A | 1.0000 |
C15—C16 | 1.370 (12) | C61—C62 | 1.3900 |
C15—H15A | 0.9500 | C61—C66 | 1.3900 |
C16—C17 | 1.392 (12) | C61—H61A | 0.9500 |
C16—H16A | 0.9500 | C62—C63 | 1.3900 |
C17—C18 | 1.389 (11) | C62—H62A | 0.9500 |
C17—H17A | 0.9500 | C63—C64 | 1.3900 |
C19—C24 | 1.530 (10) | C63—H63A | 0.9500 |
C19—C20 | 1.540 (11) | C64—C65 | 1.3900 |
C19—H19A | 0.9900 | C64—H64A | 0.9500 |
C19—H19B | 0.9900 | C65—C66 | 1.3900 |
C20—C21 | 1.500 (12) | C65—H65A | 0.9500 |
C20—H20A | 0.9900 | C79—C80 | 1.3900 |
C20—H20B | 0.9900 | C79—C84 | 1.3900 |
C21—C22 | 1.480 (13) | C79—H79A | 0.9500 |
C21—H21A | 0.9900 | C80—C81 | 1.3900 |
C21—H21B | 0.9900 | C80—H80A | 0.9500 |
C22—C23 | 1.536 (11) | C81—C82 | 1.3900 |
C22—H22A | 0.9900 | C81—H81A | 0.9500 |
C22—H22B | 0.9900 | C82—C83 | 1.3900 |
C23—C24 | 1.500 (10) | C82—H82A | 0.9500 |
C23—H23A | 0.9900 | C83—C84 | 1.3900 |
C23—H23B | 0.9900 | C83—H83A | 0.9500 |
C24—H24A | 1.0000 | C67—C72 | 1.395 (9) |
C25—C30 | 1.367 (11) | C67—C68 | 1.412 (10) |
C25—C26 | 1.393 (13) | C67—H67A | 0.9500 |
C25—H25A | 0.9500 | C68—C69 | 1.370 (10) |
C26—C27 | 1.355 (13) | C68—H68A | 0.9500 |
C26—H26A | 0.9500 | C69—C70 | 1.382 (12) |
C27—C28 | 1.378 (13) | C69—H69A | 0.9500 |
C27—H27A | 0.9500 | C70—C71 | 1.400 (12) |
C28—C29 | 1.403 (12) | C70—H70A | 0.9500 |
C28—H28A | 0.9500 | C71—C72 | 1.375 (10) |
C29—C30 | 1.381 (10) | C71—H71A | 0.9500 |
P1—Ag1—I2i | 122.00 (5) | C29—C28—H28A | 119.8 |
P1—Ag1—I1 | 113.51 (5) | C30—C29—C28 | 120.2 (8) |
I2i—Ag1—I1 | 103.73 (3) | C30—C29—H29A | 119.9 |
P1—Ag1—I2 | 109.75 (6) | C28—C29—H29A | 119.9 |
I2i—Ag1—I2 | 102.17 (4) | C25—C30—C29 | 117.8 (7) |
I1—Ag1—I2 | 103.71 (3) | C25—C30—P2 | 117.9 (5) |
P2—Ag2—I1 | 124.64 (5) | C29—C30—P2 | 124.3 (6) |
P2—Ag2—I2 | 109.52 (5) | C36—C31—C32 | 120.4 (7) |
I1—Ag2—I2 | 108.35 (2) | C36—C31—H31A | 119.8 |
P2—Ag2—I1i | 110.27 (5) | C32—C31—H31A | 119.8 |
I1—Ag2—I1i | 100.68 (3) | C33—C32—C31 | 120.6 (8) |
I2—Ag2—I1i | 100.50 (2) | C33—C32—H32A | 119.7 |
P3—Ag3—I4 | 111.91 (6) | C31—C32—H32A | 119.7 |
P3—Ag3—I3 | 118.03 (7) | C32—C33—C34 | 119.8 (8) |
I4—Ag3—I3 | 104.40 (2) | C32—C33—H33A | 120.1 |
P3—Ag3—I3ii | 116.12 (7) | C34—C33—H33A | 120.1 |
I4—Ag3—I3ii | 102.95 (3) | C35—C34—C33 | 119.7 (8) |
I3—Ag3—I3ii | 101.63 (4) | C35—C34—H34A | 120.2 |
P4—Ag4—I4 | 116.69 (5) | C33—C34—H34A | 120.2 |
P4—Ag4—I4ii | 114.43 (5) | C36—C35—C34 | 120.7 (8) |
I4—Ag4—I4ii | 105.99 (3) | C36—C35—H35A | 119.6 |
P4—Ag4—I3 | 113.15 (5) | C34—C35—H35A | 119.6 |
I4—Ag4—I3 | 102.74 (2) | C35—C36—C31 | 118.7 (7) |
I4ii—Ag4—I3 | 102.23 (2) | C35—C36—P2 | 125.0 (6) |
Ag2—I1—Ag1 | 74.23 (2) | C31—C36—P2 | 116.2 (5) |
Ag2—I1—Ag2i | 76.55 (3) | C38—C37—C42 | 112.7 (7) |
Ag1—I1—Ag2i | 74.39 (2) | C38—C37—H37A | 109.0 |
Ag1i—I2—Ag2 | 76.81 (2) | C42—C37—H37A | 109.0 |
Ag1i—I2—Ag1 | 75.36 (4) | C38—C37—H37B | 109.0 |
Ag2—I2—Ag1 | 72.05 (2) | C42—C37—H37B | 109.0 |
Ag3—I3—Ag4 | 74.43 (2) | H37A—C37—H37B | 107.8 |
Ag3—I3—Ag3ii | 76.51 (4) | C39—C38—C37 | 113.6 (7) |
Ag4—I3—Ag3ii | 74.78 (2) | C39—C38—H38A | 108.8 |
Ag3—I4—Ag4 | 74.87 (2) | C37—C38—H38A | 108.9 |
Ag3—I4—Ag4ii | 75.78 (2) | C39—C38—H38B | 108.9 |
Ag4—I4—Ag4ii | 72.57 (3) | C37—C38—H38B | 108.9 |
C18—P1—C78 | 105.6 (11) | H38A—C38—H38B | 107.7 |
C18—P1—C12 | 105.4 (5) | C38—C39—C40 | 116.1 (7) |
C18—P1—C6 | 102.9 (3) | C38—C39—H39A | 108.3 |
C78—P1—C6 | 97.5 (11) | C40—C39—H39A | 108.3 |
C12—P1—C6 | 103.0 (6) | C38—C39—H39B | 108.3 |
C18—P1—Ag1 | 114.3 (2) | C40—C39—H39B | 108.3 |
C78—P1—Ag1 | 117.5 (11) | H39A—C39—H39B | 107.4 |
C12—P1—Ag1 | 113.0 (5) | C39—C40—C41 | 112.5 (7) |
C6—P1—Ag1 | 116.7 (3) | C39—C40—H40A | 109.1 |
C30—P2—C36 | 102.5 (3) | C41—C40—H40A | 109.1 |
C30—P2—C24 | 102.5 (3) | C39—C40—H40B | 109.1 |
C36—P2—C24 | 103.5 (3) | C41—C40—H40B | 109.1 |
C30—P2—Ag2 | 116.5 (2) | H40A—C40—H40B | 107.8 |
C36—P2—Ag2 | 110.7 (2) | C42—C41—C40 | 112.7 (7) |
C24—P2—Ag2 | 119.1 (2) | C42—C41—H41A | 109.1 |
C42—P3—C90 | 100.8 (5) | C40—C41—H41A | 109.1 |
C42—P3—C48 | 105.4 (4) | C42—C41—H41B | 109.1 |
C90—P3—C48 | 102.7 (5) | C40—C41—H41B | 109.1 |
C42—P3—C54 | 113.7 (13) | H41A—C41—H41B | 107.8 |
C48—P3—C54 | 94.5 (18) | C41—C42—C37 | 110.0 (7) |
C42—P3—Ag3 | 116.7 (3) | C41—C42—P3 | 111.4 (6) |
C90—P3—Ag3 | 115.8 (4) | C37—C42—P3 | 111.9 (6) |
C48—P3—Ag3 | 113.6 (3) | C41—C42—H42A | 107.8 |
C54—P3—Ag3 | 110.6 (16) | C37—C42—H42A | 107.8 |
C66—P4—C72 | 110.2 (8) | P3—C42—H42A | 107.8 |
C66—P4—C60 | 105.8 (8) | C44—C43—C48 | 121.0 (10) |
C72—P4—C60 | 107.5 (3) | C44—C43—H43A | 119.5 |
C72—P4—C84 | 99.9 (4) | C48—C43—H43A | 119.5 |
C60—P4—C84 | 98.1 (4) | C43—C44—C45 | 119.0 (10) |
C66—P4—Ag4 | 104.5 (6) | C43—C44—H44A | 120.5 |
C72—P4—Ag4 | 115.2 (2) | C45—C44—H44A | 120.5 |
C60—P4—Ag4 | 113.3 (2) | C46—C45—C44 | 121.9 (8) |
C84—P4—Ag4 | 120.7 (3) | C46—C45—H45A | 119.1 |
C6—C1—C2 | 110.7 (7) | C44—C45—H45A | 119.1 |
C6—C1—H1A | 109.5 | C45—C46—C47 | 119.8 (10) |
C2—C1—H1A | 109.5 | C45—C46—H46A | 120.1 |
C6—C1—H1B | 109.5 | C47—C46—H46A | 120.1 |
C2—C1—H1B | 109.5 | C48—C47—C46 | 118.7 (9) |
H1A—C1—H1B | 108.1 | C48—C47—H47A | 120.6 |
C1—C2—C3 | 111.7 (7) | C46—C47—H47A | 120.6 |
C1—C2—H2A | 109.3 | C47—C48—C43 | 119.6 (7) |
C3—C2—H2A | 109.3 | C47—C48—P3 | 118.8 (6) |
C1—C2—H2B | 109.3 | C43—C48—P3 | 121.6 (7) |
C3—C2—H2B | 109.3 | C50—C49—C54 | 120.0 |
H2A—C2—H2B | 107.9 | C50—C49—H49A | 120.0 |
C4—C3—C2 | 111.3 (7) | C54—C49—H49A | 120.0 |
C4—C3—H3A | 109.4 | C51—C50—C49 | 120.0 |
C2—C3—H3A | 109.4 | C51—C50—H50A | 120.0 |
C4—C3—H3B | 109.4 | C49—C50—H50A | 120.0 |
C2—C3—H3B | 109.4 | C52—C51—C50 | 120.0 |
H3A—C3—H3B | 108.0 | C52—C51—H51A | 120.0 |
C3—C4—C5 | 111.2 (7) | C50—C51—H51A | 120.0 |
C3—C4—H4A | 109.4 | C51—C52—C53 | 120.0 |
C5—C4—H4A | 109.4 | C51—C52—H52A | 120.0 |
C3—C4—H4B | 109.4 | C53—C52—H52A | 120.0 |
C5—C4—H4B | 109.4 | C54—C53—C52 | 120.0 |
H4A—C4—H4B | 108.0 | C54—C53—H53A | 120.0 |
C6—C5—C4 | 110.4 (7) | C52—C53—H53A | 120.0 |
C6—C5—H5A | 109.6 | C53—C54—C49 | 120.0 |
C4—C5—H5A | 109.6 | C53—C54—P3 | 120 (2) |
C6—C5—H5B | 109.6 | C49—C54—P3 | 120 (2) |
C4—C5—H5B | 109.6 | C86—C85—C90 | 120.0 |
H5A—C5—H5B | 108.1 | C86—C85—H85A | 120.0 |
C1—C6—C5 | 110.6 (7) | C90—C85—H85A | 120.0 |
C1—C6—P1 | 114.0 (6) | C85—C86—C87 | 120.0 |
C5—C6—P1 | 110.2 (5) | C85—C86—H86A | 120.0 |
C1—C6—H6A | 107.2 | C87—C86—H86A | 120.0 |
C5—C6—H6A | 107.2 | C88—C87—C86 | 120.0 |
P1—C6—H6A | 107.2 | C88—C87—H87A | 120.0 |
C8—C7—C12 | 120.0 | C86—C87—H87A | 120.0 |
C8—C7—H7A | 120.0 | C87—C88—C89 | 120.0 |
C12—C7—H7A | 120.0 | C87—C88—H88A | 120.0 |
C9—C8—C7 | 120.0 | C89—C88—H88A | 120.0 |
C9—C8—H8A | 120.0 | C90—C89—C88 | 120.0 |
C7—C8—H8A | 120.0 | C90—C89—H89A | 120.0 |
C8—C9—C10 | 120.0 | C88—C89—H89A | 120.0 |
C8—C9—H9A | 120.0 | C89—C90—C85 | 120.0 |
C10—C9—H9A | 120.0 | C89—C90—P3 | 125.0 (6) |
C11—C10—C9 | 120.0 | C85—C90—P3 | 114.4 (5) |
C11—C10—H10A | 120.0 | C60—C55—C56 | 110.5 (5) |
C9—C10—H10A | 120.0 | C60—C55—H55A | 109.5 |
C12—C11—C10 | 120.0 | C56—C55—H55A | 109.5 |
C12—C11—H11A | 120.0 | C60—C55—H55B | 109.5 |
C10—C11—H11A | 120.0 | C56—C55—H55B | 109.5 |
C11—C12—C7 | 120.0 | H55A—C55—H55B | 108.1 |
C11—C12—P1 | 119.3 (9) | C57—C56—C55 | 112.0 (6) |
C7—C12—P1 | 119.5 (10) | C57—C56—H56A | 109.2 |
C74—C73—C78 | 120.0 | C55—C56—H56A | 109.2 |
C74—C73—H73A | 120.0 | C57—C56—H56B | 109.2 |
C78—C73—H73A | 120.0 | C55—C56—H56B | 109.2 |
C73—C74—C75 | 120.0 | H56A—C56—H56B | 107.9 |
C73—C74—H74A | 120.0 | C58—C57—C56 | 111.4 (6) |
C75—C74—H74A | 120.0 | C58—C57—H57A | 109.4 |
C74—C75—C76 | 120.0 | C56—C57—H57A | 109.4 |
C74—C75—H75A | 120.0 | C58—C57—H57B | 109.4 |
C76—C75—H75A | 120.0 | C56—C57—H57B | 109.4 |
C77—C76—C75 | 120.0 | H57A—C57—H57B | 108.0 |
C77—C76—H76A | 120.0 | C59—C58—C57 | 111.1 (6) |
C75—C76—H76A | 120.0 | C59—C58—H58A | 109.4 |
C76—C77—C78 | 120.0 | C57—C58—H58A | 109.4 |
C76—C77—H77A | 120.0 | C59—C58—H58B | 109.4 |
C78—C77—H77A | 120.0 | C57—C58—H58B | 109.4 |
C77—C78—C73 | 120.0 | H58A—C58—H58B | 108.0 |
C77—C78—P1 | 106 (2) | C58—C59—C60 | 111.5 (7) |
C73—C78—P1 | 134 (2) | C58—C59—H59A | 109.3 |
C14—C13—C18 | 121.0 (8) | C60—C59—H59A | 109.3 |
C14—C13—H13A | 119.5 | C58—C59—H59B | 109.3 |
C18—C13—H13A | 119.5 | C60—C59—H59B | 109.3 |
C15—C14—C13 | 120.1 (8) | H59A—C59—H59B | 108.0 |
C15—C14—H14A | 119.9 | C55—C60—C59 | 109.8 (6) |
C13—C14—H14A | 119.9 | C55—C60—P4 | 112.5 (4) |
C16—C15—C14 | 119.5 (8) | C59—C60—P4 | 109.3 (5) |
C16—C15—H15A | 120.3 | C55—C60—H60A | 108.4 |
C14—C15—H15A | 120.3 | C59—C60—H60A | 108.4 |
C15—C16—C17 | 121.1 (8) | P4—C60—H60A | 108.4 |
C15—C16—H16A | 119.5 | C62—C61—C66 | 120.0 |
C17—C16—H16A | 119.5 | C62—C61—H61A | 120.0 |
C18—C17—C16 | 119.5 (8) | C66—C61—H61A | 120.0 |
C18—C17—H17A | 120.3 | C61—C62—C63 | 120.0 |
C16—C17—H17A | 120.3 | C61—C62—H62A | 120.0 |
C13—C18—C17 | 118.7 (7) | C63—C62—H62A | 120.0 |
C13—C18—P1 | 124.7 (6) | C62—C63—C64 | 120.0 |
C17—C18—P1 | 116.3 (6) | C62—C63—H63A | 120.0 |
C24—C19—C20 | 111.2 (6) | C64—C63—H63A | 120.0 |
C24—C19—H19A | 109.4 | C65—C64—C63 | 120.0 |
C20—C19—H19A | 109.4 | C65—C64—H64A | 120.0 |
C24—C19—H19B | 109.4 | C63—C64—H64A | 120.0 |
C20—C19—H19B | 109.4 | C66—C65—C64 | 120.0 |
H19A—C19—H19B | 108.0 | C66—C65—H65A | 120.0 |
C21—C20—C19 | 111.7 (7) | C64—C65—H65A | 120.0 |
C21—C20—H20A | 109.3 | C65—C66—C61 | 120.0 |
C19—C20—H20A | 109.3 | C65—C66—P4 | 124.3 (11) |
C21—C20—H20B | 109.3 | C61—C66—P4 | 115.4 (11) |
C19—C20—H20B | 109.3 | C80—C79—C84 | 120.0 |
H20A—C20—H20B | 107.9 | C80—C79—H79A | 120.0 |
C22—C21—C20 | 113.1 (7) | C84—C79—H79A | 120.0 |
C22—C21—H21A | 109.0 | C81—C80—C79 | 120.0 |
C20—C21—H21A | 109.0 | C81—C80—H80A | 120.0 |
C22—C21—H21B | 109.0 | C79—C80—H80A | 120.0 |
C20—C21—H21B | 109.0 | C80—C81—C82 | 120.0 |
H21A—C21—H21B | 107.8 | C80—C81—H81A | 120.0 |
C21—C22—C23 | 111.9 (7) | C82—C81—H81A | 120.0 |
C21—C22—H22A | 109.2 | C83—C82—C81 | 120.0 |
C23—C22—H22A | 109.2 | C83—C82—H82A | 120.0 |
C21—C22—H22B | 109.2 | C81—C82—H82A | 120.0 |
C23—C22—H22B | 109.2 | C84—C83—C82 | 120.0 |
H22A—C22—H22B | 107.9 | C84—C83—H83A | 120.0 |
C24—C23—C22 | 110.9 (7) | C82—C83—H83A | 120.0 |
C24—C23—H23A | 109.5 | C83—C84—C79 | 120.0 |
C22—C23—H23A | 109.5 | C83—C84—P4 | 117.8 (4) |
C24—C23—H23B | 109.5 | C79—C84—P4 | 122.0 (4) |
C22—C23—H23B | 109.5 | C72—C67—C68 | 119.1 (6) |
H23A—C23—H23B | 108.0 | C72—C67—H67A | 120.4 |
C23—C24—C19 | 109.7 (6) | C68—C67—H67A | 120.4 |
C23—C24—P2 | 114.2 (5) | C69—C68—C67 | 120.3 (7) |
C19—C24—P2 | 111.3 (5) | C69—C68—H68A | 119.8 |
C23—C24—H24A | 107.1 | C67—C68—H68A | 119.8 |
C19—C24—H24A | 107.1 | C68—C69—C70 | 120.8 (7) |
P2—C24—H24A | 107.1 | C68—C69—H69A | 119.6 |
C30—C25—C26 | 122.3 (8) | C70—C69—H69A | 119.6 |
C30—C25—H25A | 118.8 | C69—C70—C71 | 118.8 (8) |
C26—C25—H25A | 118.8 | C69—C70—H70A | 120.6 |
C27—C26—C25 | 119.5 (8) | C71—C70—H70A | 120.6 |
C27—C26—H26A | 120.3 | C72—C71—C70 | 121.4 (8) |
C25—C26—H26A | 120.3 | C72—C71—H71A | 119.3 |
C26—C27—C28 | 119.7 (8) | C70—C71—H71A | 119.3 |
C26—C27—H27A | 120.2 | C71—C72—C67 | 119.5 (7) |
C28—C27—H27A | 120.2 | C71—C72—P4 | 124.9 (6) |
C27—C28—C29 | 120.3 (8) | C67—C72—P4 | 115.6 (5) |
C27—C28—H28A | 119.8 |
Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+2, y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ag4I4(C18H21P)4] |
Mr | 2012.35 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 120 |
a, b, c (Å) | 24.698 (9), 12.404 (5), 24.328 (9) |
β (°) | 104.145 (7) |
V (Å3) | 7227 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.91 |
Crystal size (mm) | 0.15 × 0.14 × 0.09 |
Data collection | |
Diffractometer | Bruker APEX |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.652, 0.767 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42119, 16990, 15397 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.107, 1.05 |
No. of reflections | 16990 |
No. of parameters | 742 |
No. of restraints | 327 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0456P)2 + 26.0708P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 2.48, −1.27 |
Absolute structure | Flack (1983), 7870 Friedel pairs |
Absolute structure parameter | −0.029 (18) |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXTL.
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The 1:1 AgI:PCyPh2 (PCyPh2 is diphenylcyclohexylphosphine) tetrameric complex is similar to reported analogues with other monodentate phosphine ligands (Bowen et al., 1994; Teo & Calabrese, 1975 and 1976; Meijboom et al., 2006). The silver and iodine atoms alternate in a distorted cubane-like AgI core with phosphine capping the silver corners (Fig. 1). Two symmetry unique but structurally similar tetramers are each located on a twofold axis. Each face is distorted such that the average Ag···Ag atomic separation is shorter than the average I···I atomic separation by about 1 Å. A closer inspection shows that the two faces completed by the twofold axis differ from each other and from the four adjacent faces in that they display the shortest and longest I···I separations for each cubane. If the face with the shortest I···I separation is assigned to be proximal, an inspection of the cyclohexyl fragments clearly show (P) helicity (Eliel et al., 1994) for both symmetry unique molecules (Fig. 2). The starting materials do not display chirality suggesting spontaneous resolution during crystallization. We also note that the proximal and distal planes could easily be inverted by slight distortion of the cubane-like core. Alternatively, concerted rotation along the Ag—P bonds would reverse the helicity. The Flack parameter refined to a value of -0.029 (18) indicating the true hand of the data has been correctly determined.