Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041384/cv2286sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041384/cv2286Isup2.hkl |
CCDC reference: 663591
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.034
- wR factor = 0.076
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was obtained by refluxing two equivalents of P(4-TolPh2) with one equivalent of CuI in acetonitrile for six hours. On cooling crystals suitable for X-ray crystallography were obtained. (Yield: 50%)
H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2 times Ueq(C aromatic) and Uiso(H) = 1.5 times Ueq(C methyl).
Atom I1 has been treated as disordered between two positions with the refined occupancies of 0.79 (4) and 0.21 (4), respectively.
The title complex, (I), is an extension of the previously investigated PPh3 (Eller et al., 1977; Liang et al., 1999) and P(4-Tol)3 (Meijboom, 2006) derivatives. The complex forms part of a range of copper(I) complexes with an iodido molecule coordinated to the metal centre. The range of coordination modes in which the iodido moiety can coordinate to the metal range from single to three centered interactions (i.e. cubane structures).
The title complex presents the most commonly observed coordination pattern for iodido copper(I) complexes, with two distinct copper(I) centres linked via an iodido bridge, see Fig. 1. Compared to previously published structures of the PPh3 (Eller et al., 1977; Liang et al., 1999) and P(4-Tol)3 (Meijboom, 2006) complexes no significant structural effect could be observed when one of the aryl substituents is functionalized. There are no significant intercalation or stacking interactions in the title compound.
Structurally related µ-iodido copper(I) complexes have been reported for PPh3 (Eller et al., 1977; Liang et al., 1999) and P(4-Tol)3 (Meijboom, 2006).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Cu2I2(C19H17P)3] | Z = 2 |
Mr = 1209.77 | F(000) = 1204 |
Triclinic, P1 | Dx = 1.587 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.984 (2) Å | Cell parameters from 9818 reflections |
b = 14.092 (5) Å | θ = 2.6–27.6° |
c = 16.084 (3) Å | µ = 2.19 mm−1 |
α = 103.948 (2)° | T = 100 K |
β = 101.743 (3)° | Block, colourless |
γ = 117.769 (4)° | 0.16 × 0.15 × 0.07 mm |
V = 2531.1 (11) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 11001 independent reflections |
Radiation source: fine-focus sealed tube | 8657 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 512 pixels mm-1 | θmax = 27.0°, θmin = 2.2° |
φ and ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −18→18 |
Tmin = 0.721, Tmax = 0.862 | l = −20→20 |
44264 measured reflections |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0282P)2 + 2.0291P] where P = (Fo2 + 2Fc2)/3 |
11001 reflections | (Δ/σ)max = 0.010 |
581 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.98 e Å−3 |
[Cu2I2(C19H17P)3] | γ = 117.769 (4)° |
Mr = 1209.77 | V = 2531.1 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.984 (2) Å | Mo Kα radiation |
b = 14.092 (5) Å | µ = 2.19 mm−1 |
c = 16.084 (3) Å | T = 100 K |
α = 103.948 (2)° | 0.16 × 0.15 × 0.07 mm |
β = 101.743 (3)° |
Bruker SMART 1K CCD area-detector diffractometer | 11001 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 8657 reflections with I > 2σ(I) |
Tmin = 0.721, Tmax = 0.862 | Rint = 0.047 |
44264 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.89 e Å−3 |
11001 reflections | Δρmin = −0.98 e Å−3 |
581 parameters |
Experimental. A disorder is observed on the methyl moieties of the tolyl group as well as one of the iodido groups. |
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) | |
I1 | 0.7341 (3) | 0.5527 (3) | 0.3950 (3) | 0.0229 (3) | 0.79 (4) |
I2 | 0.71959 (2) | 0.307168 (19) | 0.154947 (17) | 0.03187 (7) | |
Cu2 | 0.79801 (3) | 0.51480 (3) | 0.25878 (3) | 0.02518 (10) | |
Cu1 | 0.59671 (3) | 0.33342 (3) | 0.25824 (3) | 0.02458 (10) | |
P2 | 0.43984 (7) | 0.31991 (8) | 0.16951 (6) | 0.0260 (2) | |
P1 | 0.57986 (8) | 0.20772 (8) | 0.32759 (7) | 0.0274 (2) | |
P3 | 0.94695 (7) | 0.65489 (8) | 0.24280 (6) | 0.0264 (2) | |
C11 | 0.7117 (3) | 0.2117 (3) | 0.3774 (2) | 0.0267 (7) | |
C41 | 0.3348 (3) | 0.3020 (3) | 0.2255 (2) | 0.0289 (8) | |
C31 | 0.5205 (3) | 0.2125 (3) | 0.4187 (3) | 0.0326 (8) | |
C72 | 1.0760 (3) | 0.5883 (3) | 0.3379 (3) | 0.0343 (9) | |
H72 | 1.0138 | 0.5555 | 0.3569 | 0.041* | |
C21 | 0.4767 (3) | 0.0587 (3) | 0.2438 (3) | 0.0332 (8) | |
C46 | 0.3639 (3) | 0.3952 (3) | 0.3024 (2) | 0.0337 (8) | |
H46 | 0.4328 | 0.4666 | 0.3209 | 0.040* | |
C51 | 0.4678 (3) | 0.4474 (3) | 0.1426 (2) | 0.0287 (8) | |
C34 | 0.4276 (3) | 0.2242 (3) | 0.5571 (3) | 0.0391 (9) | |
C15 | 0.8127 (4) | 0.1300 (4) | 0.4397 (3) | 0.0391 (9) | |
H15 | 0.8105 | 0.0689 | 0.4537 | 0.047* | |
C56 | 0.5720 (3) | 0.5111 (3) | 0.1320 (2) | 0.0310 (8) | |
H56 | 0.6243 | 0.4877 | 0.1380 | 0.037* | |
C61 | 0.3544 (3) | 0.1981 (3) | 0.0583 (2) | 0.0287 (8) | |
C26 | 0.3589 (3) | 0.0108 (3) | 0.2253 (3) | 0.0416 (10) | |
H26 | 0.3344 | 0.0501 | 0.2614 | 0.050* | |
C91 | 0.9365 (3) | 0.6554 (3) | 0.1282 (2) | 0.0313 (8) | |
C43 | 0.1619 (4) | 0.1836 (4) | 0.2508 (3) | 0.0500 (11) | |
H43 | 0.0940 | 0.1118 | 0.2336 | 0.060* | |
C16 | 0.7105 (3) | 0.1195 (3) | 0.3960 (3) | 0.0336 (8) | |
H16 | 0.6399 | 0.0501 | 0.3787 | 0.040* | |
C81 | 0.9948 (3) | 0.8033 (3) | 0.3089 (2) | 0.0334 (8) | |
C32 | 0.4914 (3) | 0.2935 (3) | 0.4438 (2) | 0.0266 (7) | |
H32 | 0.5032 | 0.3451 | 0.4144 | 0.032* | |
C22 | 0.5116 (3) | −0.0002 (3) | 0.1875 (3) | 0.0421 (10) | |
H22 | 0.5902 | 0.0323 | 0.1979 | 0.051* | |
C12 | 0.8182 (3) | 0.3118 (3) | 0.4001 (2) | 0.0320 (8) | |
H12 | 0.8212 | 0.3738 | 0.3874 | 0.038* | |
C64 | 0.2260 (3) | 0.0081 (3) | −0.1122 (3) | 0.0381 (9) | |
C94 | 0.9349 (4) | 0.6509 (6) | −0.0475 (3) | 0.0674 (11) | |
C84 | 1.0531 (7) | 1.0281 (4) | 0.3995 (4) | 0.085 (2) | |
H84 | 1.0729 | 1.1031 | 0.4314 | 0.102* | |
C14 | 0.9178 (4) | 0.2301 (4) | 0.4626 (3) | 0.0394 (9) | |
H14 | 0.9867 | 0.2371 | 0.4919 | 0.047* | |
C45 | 0.2910 (3) | 0.3828 (4) | 0.3517 (3) | 0.0411 (10) | |
H45 | 0.3103 | 0.4462 | 0.4020 | 0.049* | |
C44 | 0.1903 (4) | 0.2768 (4) | 0.3260 (3) | 0.0509 (11) | |
H44 | 0.1417 | 0.2681 | 0.3593 | 0.061* | |
C62 | 0.3765 (3) | 0.1103 (3) | 0.0388 (2) | 0.0320 (8) | |
H62 | 0.4350 | 0.1148 | 0.0826 | 0.038* | |
C33 | 0.4449 (3) | 0.2995 (3) | 0.5119 (2) | 0.0303 (8) | |
H33 | 0.4253 | 0.3543 | 0.5273 | 0.036* | |
C54 | 0.5225 (4) | 0.6445 (4) | 0.1023 (3) | 0.0469 (11) | |
H54 | 0.5408 | 0.7104 | 0.0892 | 0.056* | |
C13 | 0.9202 (3) | 0.3201 (3) | 0.4416 (3) | 0.0370 (9) | |
H13 | 0.9912 | 0.3873 | 0.4556 | 0.044* | |
C66 | 0.2666 (3) | 0.1889 (3) | −0.0092 (3) | 0.0339 (8) | |
H66 | 0.2502 | 0.2465 | 0.0023 | 0.041* | |
C96 | 0.9597 (3) | 0.7513 (4) | 0.1066 (3) | 0.0400 (9) | |
H96 | 0.9762 | 0.8186 | 0.1511 | 0.048* | |
C63 | 0.3125 (3) | 0.0162 (3) | −0.0451 (3) | 0.0366 (9) | |
H63 | 0.3277 | −0.0423 | −0.0565 | 0.044* | |
C341 | 0.3806 (4) | 0.2300 (4) | 0.6334 (3) | 0.0543 (12) | |
H34A | 0.3660 | 0.2912 | 0.6432 | 0.081* | 0.50 |
H34B | 0.4364 | 0.2453 | 0.6890 | 0.081* | 0.50 |
H34C | 0.3094 | 0.1572 | 0.6166 | 0.081* | 0.50 |
H34D | 0.3752 | 0.1713 | 0.6560 | 0.081* | 0.50 |
H34E | 0.3049 | 0.2172 | 0.6101 | 0.081* | 0.50 |
H34F | 0.4318 | 0.3053 | 0.6826 | 0.081* | 0.50 |
C36 | 0.4995 (5) | 0.1357 (4) | 0.4628 (4) | 0.0637 (15) | |
H36 | 0.5164 | 0.0789 | 0.4464 | 0.076* | |
C52 | 0.3906 (3) | 0.4840 (4) | 0.1322 (3) | 0.0393 (9) | |
H52 | 0.3200 | 0.4428 | 0.1391 | 0.047* | |
C71 | 1.0733 (3) | 0.6445 (3) | 0.2791 (3) | 0.0338 (8) | |
C65 | 0.2040 (3) | 0.0956 (3) | −0.0927 (3) | 0.0373 (9) | |
H65 | 0.1458 | 0.0912 | −0.1367 | 0.045* | |
C83 | 1.1370 (5) | 1.0091 (4) | 0.3875 (3) | 0.0772 (18) | |
H83 | 1.2136 | 1.0716 | 0.4093 | 0.093* | |
C76 | 1.1659 (3) | 0.6917 (4) | 0.2500 (3) | 0.0545 (13) | |
H76 | 1.1643 | 0.7290 | 0.2097 | 0.065* | |
C73 | 1.1714 (4) | 0.5807 (4) | 0.3689 (3) | 0.0485 (11) | |
H73 | 1.1739 | 0.5440 | 0.4095 | 0.058* | |
C23 | 0.4298 (4) | −0.1069 (3) | 0.1161 (3) | 0.0500 (11) | |
H23 | 0.4539 | −0.1470 | 0.0803 | 0.060* | |
C24 | 0.3130 (4) | −0.1541 (4) | 0.0979 (3) | 0.0545 (12) | |
H24 | 0.2583 | −0.2247 | 0.0488 | 0.065* | |
C42 | 0.2340 (3) | 0.1957 (4) | 0.2002 (3) | 0.0399 (9) | |
H42 | 0.2141 | 0.1322 | 0.1495 | 0.048* | |
C93 | 0.9070 (5) | 0.5532 (5) | −0.0271 (3) | 0.0646 (14) | |
H93 | 0.8876 | 0.4852 | −0.0725 | 0.077* | |
C92 | 0.9076 (4) | 0.5550 (4) | 0.0590 (3) | 0.0538 (12) | |
H92 | 0.8885 | 0.4884 | 0.0709 | 0.065* | |
C74 | 1.2623 (4) | 0.6276 (5) | 0.3394 (4) | 0.0650 (15) | |
H74 | 1.3256 | 0.6214 | 0.3594 | 0.078* | |
C95 | 0.9587 (4) | 0.7487 (4) | 0.0200 (3) | 0.0503 (11) | |
H95 | 0.9744 | 0.8142 | 0.0071 | 0.060* | |
C25 | 0.2777 (3) | −0.0957 (4) | 0.1531 (3) | 0.0505 (11) | |
H25 | 0.1989 | −0.1280 | 0.1417 | 0.061* | |
C53 | 0.4185 (4) | 0.5809 (4) | 0.1118 (3) | 0.0495 (11) | |
H53 | 0.3658 | 0.6038 | 0.1044 | 0.059* | |
C82 | 1.1094 (4) | 0.8966 (4) | 0.3427 (3) | 0.0513 (12) | |
H82 | 1.1674 | 0.8841 | 0.3356 | 0.062* | |
C75 | 1.2603 (4) | 0.6834 (5) | 0.2808 (4) | 0.0665 (15) | |
H75 | 1.3225 | 0.7157 | 0.2618 | 0.080* | |
C55 | 0.5994 (4) | 0.6088 (3) | 0.1126 (3) | 0.0399 (9) | |
H55 | 0.6703 | 0.6510 | 0.1065 | 0.048* | |
C35 | 0.4539 (5) | 0.1422 (4) | 0.5305 (4) | 0.0652 (15) | |
H35 | 0.4406 | 0.0895 | 0.5590 | 0.078* | |
C85 | 0.9388 (6) | 0.9366 (4) | 0.3647 (4) | 0.0785 (18) | |
H85 | 0.8813 | 0.9504 | 0.3712 | 0.094* | |
C941 | 0.9443 (4) | 0.6557 (5) | −0.1376 (3) | 0.0674 (11) | |
H94A | 0.9252 | 0.5815 | −0.1774 | 0.101* | 0.50 |
H94B | 1.0222 | 0.7144 | −0.1274 | 0.101* | 0.50 |
H94C | 0.8913 | 0.6741 | −0.1659 | 0.101* | 0.50 |
H94D | 0.9673 | 0.7318 | −0.1364 | 0.101* | 0.50 |
H94E | 0.8703 | 0.5989 | −0.1864 | 0.101* | 0.50 |
H94F | 1.0012 | 0.6392 | −0.1479 | 0.101* | 0.50 |
C86 | 0.9093 (4) | 0.8241 (4) | 0.3200 (3) | 0.0518 (12) | |
H86 | 0.8322 | 0.7624 | 0.2973 | 0.062* | |
C641 | 0.1583 (4) | −0.0910 (4) | −0.2036 (3) | 0.0666 (14) | |
H64A | 0.1027 | −0.0816 | −0.2405 | 0.100* | 0.50 |
H64B | 0.1185 | −0.1626 | −0.1951 | 0.100* | 0.50 |
H64C | 0.2102 | −0.0926 | −0.2340 | 0.100* | 0.50 |
H64D | 0.1849 | −0.1429 | −0.2059 | 0.100* | 0.50 |
H64E | 0.1691 | −0.0619 | −0.2513 | 0.100* | 0.50 |
H64F | 0.0774 | −0.1320 | −0.2124 | 0.100* | 0.50 |
I3 | 0.722 (2) | 0.5469 (15) | 0.381 (2) | 0.032 (2) | 0.21 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0197 (5) | 0.0244 (4) | 0.0226 (8) | 0.0103 (4) | 0.0102 (5) | 0.0076 (5) |
I2 | 0.02803 (13) | 0.02857 (12) | 0.03736 (15) | 0.01492 (10) | 0.01749 (11) | 0.00656 (10) |
Cu2 | 0.0211 (2) | 0.0268 (2) | 0.0296 (2) | 0.01260 (18) | 0.01282 (18) | 0.01188 (18) |
Cu1 | 0.0204 (2) | 0.0253 (2) | 0.0295 (2) | 0.01191 (18) | 0.01177 (18) | 0.01153 (17) |
P2 | 0.0199 (4) | 0.0307 (5) | 0.0274 (5) | 0.0134 (4) | 0.0108 (4) | 0.0103 (4) |
P1 | 0.0255 (5) | 0.0243 (4) | 0.0364 (5) | 0.0127 (4) | 0.0175 (4) | 0.0142 (4) |
P3 | 0.0201 (4) | 0.0342 (5) | 0.0292 (5) | 0.0140 (4) | 0.0132 (4) | 0.0167 (4) |
C11 | 0.0314 (19) | 0.0310 (18) | 0.0241 (18) | 0.0186 (16) | 0.0150 (15) | 0.0128 (15) |
C41 | 0.0267 (18) | 0.039 (2) | 0.0270 (19) | 0.0203 (17) | 0.0122 (15) | 0.0156 (16) |
C31 | 0.031 (2) | 0.0285 (19) | 0.045 (2) | 0.0149 (17) | 0.0230 (18) | 0.0194 (17) |
C72 | 0.0271 (19) | 0.048 (2) | 0.036 (2) | 0.0200 (18) | 0.0178 (17) | 0.0240 (18) |
C21 | 0.030 (2) | 0.0240 (18) | 0.042 (2) | 0.0104 (16) | 0.0158 (17) | 0.0147 (16) |
C46 | 0.032 (2) | 0.045 (2) | 0.030 (2) | 0.0241 (18) | 0.0125 (16) | 0.0164 (17) |
C51 | 0.0289 (19) | 0.0340 (19) | 0.0253 (19) | 0.0191 (17) | 0.0092 (15) | 0.0109 (15) |
C34 | 0.035 (2) | 0.042 (2) | 0.045 (2) | 0.0176 (19) | 0.0267 (19) | 0.0211 (19) |
C15 | 0.056 (3) | 0.048 (2) | 0.037 (2) | 0.039 (2) | 0.023 (2) | 0.0245 (19) |
C56 | 0.030 (2) | 0.036 (2) | 0.0268 (19) | 0.0179 (17) | 0.0081 (16) | 0.0133 (16) |
C61 | 0.0206 (17) | 0.0327 (19) | 0.031 (2) | 0.0111 (15) | 0.0133 (15) | 0.0127 (15) |
C26 | 0.033 (2) | 0.035 (2) | 0.060 (3) | 0.0150 (18) | 0.024 (2) | 0.025 (2) |
C91 | 0.0231 (18) | 0.052 (2) | 0.031 (2) | 0.0232 (18) | 0.0162 (16) | 0.0229 (18) |
C43 | 0.033 (2) | 0.049 (3) | 0.063 (3) | 0.015 (2) | 0.029 (2) | 0.022 (2) |
C16 | 0.040 (2) | 0.0307 (19) | 0.037 (2) | 0.0187 (18) | 0.0224 (18) | 0.0175 (16) |
C81 | 0.037 (2) | 0.032 (2) | 0.028 (2) | 0.0117 (17) | 0.0124 (17) | 0.0189 (16) |
C32 | 0.0214 (17) | 0.0294 (18) | 0.0263 (19) | 0.0112 (15) | 0.0092 (14) | 0.0122 (15) |
C22 | 0.034 (2) | 0.034 (2) | 0.046 (3) | 0.0110 (18) | 0.0178 (19) | 0.0087 (18) |
C12 | 0.034 (2) | 0.0312 (19) | 0.037 (2) | 0.0185 (17) | 0.0172 (17) | 0.0169 (16) |
C64 | 0.026 (2) | 0.040 (2) | 0.029 (2) | 0.0082 (17) | 0.0095 (16) | 0.0056 (17) |
C94 | 0.069 (2) | 0.130 (3) | 0.050 (2) | 0.073 (3) | 0.0374 (19) | 0.054 (2) |
C84 | 0.146 (6) | 0.032 (3) | 0.055 (3) | 0.024 (4) | 0.058 (4) | 0.018 (2) |
C14 | 0.041 (2) | 0.052 (3) | 0.039 (2) | 0.033 (2) | 0.0169 (19) | 0.0219 (19) |
C45 | 0.042 (2) | 0.061 (3) | 0.036 (2) | 0.035 (2) | 0.0214 (19) | 0.021 (2) |
C44 | 0.042 (3) | 0.067 (3) | 0.059 (3) | 0.032 (2) | 0.036 (2) | 0.030 (2) |
C62 | 0.0234 (18) | 0.040 (2) | 0.030 (2) | 0.0169 (17) | 0.0099 (16) | 0.0108 (16) |
C33 | 0.0219 (18) | 0.035 (2) | 0.030 (2) | 0.0142 (16) | 0.0089 (15) | 0.0089 (16) |
C54 | 0.061 (3) | 0.042 (2) | 0.049 (3) | 0.033 (2) | 0.021 (2) | 0.024 (2) |
C13 | 0.032 (2) | 0.040 (2) | 0.041 (2) | 0.0200 (18) | 0.0159 (18) | 0.0168 (18) |
C66 | 0.0263 (19) | 0.035 (2) | 0.037 (2) | 0.0137 (17) | 0.0114 (17) | 0.0148 (17) |
C96 | 0.031 (2) | 0.059 (3) | 0.044 (2) | 0.026 (2) | 0.0173 (18) | 0.033 (2) |
C63 | 0.029 (2) | 0.037 (2) | 0.036 (2) | 0.0175 (18) | 0.0109 (17) | 0.0058 (17) |
C341 | 0.063 (3) | 0.052 (3) | 0.069 (3) | 0.036 (2) | 0.045 (3) | 0.031 (2) |
C36 | 0.101 (4) | 0.063 (3) | 0.104 (4) | 0.064 (3) | 0.086 (4) | 0.067 (3) |
C52 | 0.040 (2) | 0.058 (3) | 0.041 (2) | 0.035 (2) | 0.0236 (19) | 0.025 (2) |
C71 | 0.0265 (19) | 0.051 (2) | 0.033 (2) | 0.0224 (18) | 0.0168 (16) | 0.0226 (18) |
C65 | 0.0251 (19) | 0.041 (2) | 0.033 (2) | 0.0138 (18) | 0.0045 (16) | 0.0105 (17) |
C83 | 0.084 (4) | 0.043 (3) | 0.040 (3) | −0.005 (3) | 0.002 (3) | 0.017 (2) |
C76 | 0.034 (2) | 0.098 (4) | 0.059 (3) | 0.038 (3) | 0.028 (2) | 0.058 (3) |
C73 | 0.043 (2) | 0.080 (3) | 0.050 (3) | 0.042 (2) | 0.022 (2) | 0.043 (2) |
C23 | 0.046 (3) | 0.036 (2) | 0.044 (3) | 0.010 (2) | 0.018 (2) | 0.0043 (19) |
C24 | 0.046 (3) | 0.034 (2) | 0.048 (3) | 0.002 (2) | 0.009 (2) | 0.009 (2) |
C42 | 0.032 (2) | 0.047 (2) | 0.047 (2) | 0.0217 (19) | 0.0223 (19) | 0.0200 (19) |
C93 | 0.094 (4) | 0.099 (4) | 0.042 (3) | 0.076 (4) | 0.037 (3) | 0.031 (3) |
C92 | 0.072 (3) | 0.076 (3) | 0.045 (3) | 0.052 (3) | 0.033 (2) | 0.036 (2) |
C74 | 0.039 (3) | 0.117 (4) | 0.077 (4) | 0.054 (3) | 0.030 (3) | 0.062 (3) |
C95 | 0.040 (2) | 0.086 (3) | 0.051 (3) | 0.039 (2) | 0.027 (2) | 0.048 (3) |
C25 | 0.024 (2) | 0.039 (2) | 0.066 (3) | 0.0012 (18) | 0.014 (2) | 0.023 (2) |
C53 | 0.067 (3) | 0.063 (3) | 0.048 (3) | 0.054 (3) | 0.026 (2) | 0.025 (2) |
C82 | 0.043 (3) | 0.044 (3) | 0.041 (3) | 0.008 (2) | 0.001 (2) | 0.023 (2) |
C75 | 0.041 (3) | 0.123 (5) | 0.078 (4) | 0.053 (3) | 0.039 (3) | 0.069 (3) |
C55 | 0.044 (2) | 0.040 (2) | 0.036 (2) | 0.021 (2) | 0.0130 (19) | 0.0207 (18) |
C35 | 0.104 (4) | 0.064 (3) | 0.102 (4) | 0.064 (3) | 0.085 (4) | 0.067 (3) |
C85 | 0.126 (5) | 0.048 (3) | 0.100 (4) | 0.050 (3) | 0.088 (4) | 0.043 (3) |
C941 | 0.069 (2) | 0.130 (3) | 0.050 (2) | 0.073 (3) | 0.0374 (19) | 0.054 (2) |
C86 | 0.068 (3) | 0.038 (2) | 0.069 (3) | 0.030 (2) | 0.050 (3) | 0.029 (2) |
C641 | 0.046 (3) | 0.069 (3) | 0.064 (3) | 0.027 (3) | 0.013 (2) | 0.008 (3) |
I3 | 0.034 (4) | 0.0266 (16) | 0.030 (5) | 0.012 (2) | 0.015 (4) | 0.008 (2) |
I1—Cu2 | 2.561 (4) | C84—H84 | 0.9300 |
I1—Cu1 | 2.747 (4) | C14—C13 | 1.376 (5) |
I2—Cu2 | 2.5421 (10) | C14—H14 | 0.9300 |
I2—Cu1 | 2.7033 (8) | C45—C44 | 1.375 (6) |
Cu2—P3 | 2.2209 (11) | C45—H45 | 0.9300 |
Cu2—I3 | 2.469 (17) | C44—H44 | 0.9300 |
Cu2—Cu1 | 2.7807 (9) | C62—C63 | 1.385 (5) |
Cu1—P2 | 2.2562 (12) | C62—H62 | 0.9300 |
Cu1—P1 | 2.2601 (12) | C33—H33 | 0.9300 |
Cu1—I3 | 2.62 (2) | C54—C53 | 1.373 (6) |
P2—C61 | 1.820 (4) | C54—C55 | 1.382 (5) |
P2—C41 | 1.826 (3) | C54—H54 | 0.9300 |
P2—C51 | 1.832 (4) | C13—H13 | 0.9300 |
P1—C11 | 1.824 (4) | C66—C65 | 1.377 (5) |
P1—C21 | 1.825 (4) | C66—H66 | 0.9300 |
P1—C31 | 1.828 (4) | C96—C95 | 1.382 (5) |
P3—C81 | 1.813 (4) | C96—H96 | 0.9300 |
P3—C91 | 1.822 (4) | C63—H63 | 0.9300 |
P3—C71 | 1.829 (4) | C341—H34A | 0.9600 |
C11—C12 | 1.383 (5) | C341—H34B | 0.9600 |
C11—C16 | 1.395 (5) | C341—H34C | 0.9600 |
C41—C42 | 1.379 (5) | C341—H34D | 0.9600 |
C41—C46 | 1.391 (5) | C341—H34E | 0.9600 |
C31—C32 | 1.382 (5) | C341—H34F | 0.9600 |
C31—C36 | 1.386 (5) | C36—C35 | 1.373 (6) |
C72—C71 | 1.378 (5) | C36—H36 | 0.9300 |
C72—C73 | 1.389 (5) | C52—C53 | 1.377 (6) |
C72—H72 | 0.9300 | C52—H52 | 0.9300 |
C21—C26 | 1.388 (5) | C71—C76 | 1.390 (5) |
C21—C22 | 1.394 (5) | C65—H65 | 0.9300 |
C46—C45 | 1.388 (5) | C83—C82 | 1.395 (7) |
C46—H46 | 0.9300 | C83—H83 | 0.9300 |
C51—C56 | 1.384 (5) | C76—C75 | 1.381 (6) |
C51—C52 | 1.396 (5) | C76—H76 | 0.9300 |
C34—C35 | 1.371 (5) | C73—C74 | 1.376 (6) |
C34—C33 | 1.384 (5) | C73—H73 | 0.9300 |
C34—C341 | 1.508 (5) | C23—C24 | 1.377 (6) |
C15—C14 | 1.372 (5) | C23—H23 | 0.9300 |
C15—C16 | 1.380 (5) | C24—C25 | 1.384 (6) |
C15—H15 | 0.9300 | C24—H24 | 0.9300 |
C56—C55 | 1.379 (5) | C42—H42 | 0.9300 |
C56—H56 | 0.9300 | C93—C92 | 1.377 (6) |
C61—C62 | 1.390 (5) | C93—H93 | 0.9300 |
C61—C66 | 1.395 (5) | C92—H92 | 0.9300 |
C26—C25 | 1.387 (6) | C74—C75 | 1.369 (6) |
C26—H26 | 0.9300 | C74—H74 | 0.9300 |
C91—C96 | 1.384 (5) | C95—H95 | 0.9300 |
C91—C92 | 1.389 (6) | C25—H25 | 0.9300 |
C43—C44 | 1.378 (6) | C53—H53 | 0.9300 |
C43—C42 | 1.397 (5) | C82—H82 | 0.9300 |
C43—H43 | 0.9300 | C75—H75 | 0.9300 |
C16—H16 | 0.9300 | C55—H55 | 0.9300 |
C81—C82 | 1.389 (5) | C35—H35 | 0.9300 |
C81—C86 | 1.392 (5) | C85—C86 | 1.386 (6) |
C32—C33 | 1.389 (5) | C85—H85 | 0.9300 |
C32—H32 | 0.9300 | C941—H94A | 0.9600 |
C22—C23 | 1.385 (5) | C941—H94B | 0.9600 |
C22—H22 | 0.9300 | C941—H94C | 0.9600 |
C12—C13 | 1.383 (5) | C941—H94D | 0.9600 |
C12—H12 | 0.9300 | C941—H94E | 0.9600 |
C64—C65 | 1.385 (5) | C941—H94F | 0.9600 |
C64—C63 | 1.387 (5) | C86—H86 | 0.9300 |
C64—C641 | 1.490 (6) | C641—H64A | 0.9600 |
C94—C95 | 1.376 (7) | C641—H64B | 0.9600 |
C94—C93 | 1.387 (7) | C641—H64C | 0.9600 |
C94—C941 | 1.496 (6) | C641—H64D | 0.9600 |
C84—C83 | 1.359 (8) | C641—H64E | 0.9600 |
C84—C85 | 1.378 (8) | C641—H64F | 0.9600 |
Cu2—I1—Cu1 | 63.07 (9) | C95—C96—H96 | 119.5 |
Cu2—I2—Cu1 | 63.941 (18) | C91—C96—H96 | 119.5 |
P3—Cu2—I3 | 124.3 (4) | C62—C63—C64 | 120.8 (4) |
P3—Cu2—I2 | 116.50 (3) | C62—C63—H63 | 119.6 |
I3—Cu2—I2 | 118.7 (4) | C64—C63—H63 | 119.6 |
P3—Cu2—I1 | 122.44 (9) | C34—C341—H34A | 109.5 |
I3—Cu2—I1 | 4.6 (7) | C34—C341—H34B | 109.5 |
I2—Cu2—I1 | 119.85 (9) | H34A—C341—H34B | 109.5 |
P3—Cu2—Cu1 | 173.43 (3) | C34—C341—H34C | 109.5 |
I3—Cu2—Cu1 | 59.4 (5) | H34A—C341—H34C | 109.5 |
I2—Cu2—Cu1 | 60.85 (2) | H34B—C341—H34C | 109.5 |
I1—Cu2—Cu1 | 61.74 (9) | C34—C341—H34D | 109.5 |
P2—Cu1—P1 | 121.94 (4) | H34A—C341—H34D | 141.1 |
P2—Cu1—I3 | 104.5 (6) | H34B—C341—H34D | 56.3 |
P1—Cu1—I3 | 110.1 (6) | H34C—C341—H34D | 56.3 |
P2—Cu1—I2 | 109.14 (4) | C34—C341—H34E | 109.5 |
P1—Cu1—I2 | 102.33 (3) | H34A—C341—H34E | 56.3 |
I3—Cu1—I2 | 108.3 (3) | H34B—C341—H34E | 141.1 |
P2—Cu1—I1 | 107.95 (9) | H34C—C341—H34E | 56.3 |
P1—Cu1—I1 | 106.56 (11) | H34D—C341—H34E | 109.5 |
I3—Cu1—I1 | 3.8 (7) | C34—C341—H34F | 109.5 |
I2—Cu1—I1 | 108.23 (7) | H34A—C341—H34F | 56.3 |
P2—Cu1—Cu2 | 109.66 (4) | H34B—C341—H34F | 56.3 |
P1—Cu1—Cu2 | 128.35 (3) | H34C—C341—H34F | 141.1 |
I3—Cu1—Cu2 | 54.4 (3) | H34D—C341—H34F | 109.5 |
I2—Cu1—Cu2 | 55.21 (2) | H34E—C341—H34F | 109.5 |
I1—Cu1—Cu2 | 55.19 (8) | C35—C36—C31 | 120.9 (4) |
C61—P2—C41 | 103.73 (16) | C35—C36—H36 | 119.6 |
C61—P2—C51 | 104.49 (16) | C31—C36—H36 | 119.6 |
C41—P2—C51 | 103.13 (16) | C53—C52—C51 | 120.3 (4) |
C61—P2—Cu1 | 116.33 (12) | C53—C52—H52 | 119.9 |
C41—P2—Cu1 | 111.73 (12) | C51—C52—H52 | 119.9 |
C51—P2—Cu1 | 115.91 (11) | C72—C71—C76 | 119.4 (3) |
C11—P1—C21 | 104.78 (16) | C72—C71—P3 | 118.2 (3) |
C11—P1—C31 | 104.50 (17) | C76—C71—P3 | 122.4 (3) |
C21—P1—C31 | 102.44 (17) | C66—C65—C64 | 121.2 (4) |
C11—P1—Cu1 | 116.45 (12) | C66—C65—H65 | 119.4 |
C21—P1—Cu1 | 109.69 (13) | C64—C65—H65 | 119.4 |
C31—P1—Cu1 | 117.40 (12) | C84—C83—C82 | 120.6 (5) |
C81—P3—C91 | 102.06 (17) | C84—C83—H83 | 119.7 |
C81—P3—C71 | 105.71 (18) | C82—C83—H83 | 119.7 |
C91—P3—C71 | 102.79 (16) | C75—C76—C71 | 120.1 (4) |
C81—P3—Cu2 | 116.76 (12) | C75—C76—H76 | 119.9 |
C91—P3—Cu2 | 119.02 (12) | C71—C76—H76 | 119.9 |
C71—P3—Cu2 | 108.92 (13) | C74—C73—C72 | 119.7 (4) |
C12—C11—C16 | 118.2 (3) | C74—C73—H73 | 120.1 |
C12—C11—P1 | 118.7 (3) | C72—C73—H73 | 120.1 |
C16—C11—P1 | 123.1 (3) | C24—C23—C22 | 120.5 (4) |
C42—C41—C46 | 119.2 (3) | C24—C23—H23 | 119.8 |
C42—C41—P2 | 121.8 (3) | C22—C23—H23 | 119.8 |
C46—C41—P2 | 118.6 (3) | C23—C24—C25 | 119.5 (4) |
C32—C31—C36 | 117.5 (3) | C23—C24—H24 | 120.2 |
C32—C31—P1 | 119.4 (3) | C25—C24—H24 | 120.2 |
C36—C31—P1 | 123.0 (3) | C41—C42—C43 | 119.8 (4) |
C71—C72—C73 | 120.1 (3) | C41—C42—H42 | 120.1 |
C71—C72—H72 | 119.9 | C43—C42—H42 | 120.1 |
C73—C72—H72 | 119.9 | C92—C93—C94 | 121.3 (5) |
C26—C21—C22 | 119.1 (3) | C92—C93—H93 | 119.4 |
C26—C21—P1 | 118.8 (3) | C94—C93—H93 | 119.4 |
C22—C21—P1 | 121.3 (3) | C93—C92—C91 | 120.7 (4) |
C45—C46—C41 | 120.7 (4) | C93—C92—H92 | 119.7 |
C45—C46—H46 | 119.7 | C91—C92—H92 | 119.7 |
C41—C46—H46 | 119.7 | C75—C74—C73 | 120.5 (4) |
C56—C51—C52 | 118.1 (3) | C75—C74—H74 | 119.7 |
C56—C51—P2 | 117.9 (3) | C73—C74—H74 | 119.7 |
C52—C51—P2 | 124.0 (3) | C94—C95—C96 | 121.2 (5) |
C35—C34—C33 | 118.1 (4) | C94—C95—H95 | 119.4 |
C35—C34—C341 | 119.9 (4) | C96—C95—H95 | 119.4 |
C33—C34—C341 | 122.0 (4) | C24—C25—C26 | 120.5 (4) |
C14—C15—C16 | 120.4 (4) | C24—C25—H25 | 119.8 |
C14—C15—H15 | 119.8 | C26—C25—H25 | 119.8 |
C16—C15—H15 | 119.8 | C54—C53—C52 | 121.4 (4) |
C55—C56—C51 | 121.0 (3) | C54—C53—H53 | 119.3 |
C55—C56—H56 | 119.5 | C52—C53—H53 | 119.3 |
C51—C56—H56 | 119.5 | C81—C82—C83 | 119.8 (5) |
C62—C61—C66 | 118.0 (3) | C81—C82—H82 | 120.1 |
C62—C61—P2 | 119.5 (3) | C83—C82—H82 | 120.1 |
C66—C61—P2 | 122.4 (3) | C74—C75—C76 | 120.0 (4) |
C25—C26—C21 | 120.1 (4) | C74—C75—H75 | 120.0 |
C25—C26—H26 | 119.9 | C76—C75—H75 | 120.0 |
C21—C26—H26 | 119.9 | C56—C55—C54 | 120.6 (4) |
C96—C91—C92 | 117.9 (4) | C56—C55—H55 | 119.7 |
C96—C91—P3 | 123.9 (3) | C54—C55—H55 | 119.7 |
C92—C91—P3 | 118.1 (3) | C34—C35—C36 | 121.7 (4) |
C44—C43—C42 | 120.8 (4) | C34—C35—H35 | 119.1 |
C44—C43—H43 | 119.6 | C36—C35—H35 | 119.1 |
C42—C43—H43 | 119.6 | C84—C85—C86 | 120.1 (5) |
C15—C16—C11 | 120.8 (4) | C84—C85—H85 | 119.9 |
C15—C16—H16 | 119.6 | C86—C85—H85 | 119.9 |
C11—C16—H16 | 119.6 | C94—C941—H94A | 109.5 |
C82—C81—C86 | 119.1 (4) | C94—C941—H94B | 109.5 |
C82—C81—P3 | 123.7 (3) | H94A—C941—H94B | 109.5 |
C86—C81—P3 | 117.0 (3) | C94—C941—H94C | 109.5 |
C31—C32—C33 | 121.4 (3) | H94A—C941—H94C | 109.5 |
C31—C32—H32 | 119.3 | H94B—C941—H94C | 109.5 |
C33—C32—H32 | 119.3 | C94—C941—H94D | 109.5 |
C23—C22—C21 | 120.3 (4) | H94A—C941—H94D | 141.1 |
C23—C22—H22 | 119.9 | H94B—C941—H94D | 56.3 |
C21—C22—H22 | 119.9 | H94C—C941—H94D | 56.3 |
C13—C12—C11 | 120.5 (3) | C94—C941—H94E | 109.5 |
C13—C12—H12 | 119.8 | H94A—C941—H94E | 56.3 |
C11—C12—H12 | 119.8 | H94B—C941—H94E | 141.1 |
C65—C64—C63 | 118.3 (3) | H94C—C941—H94E | 56.3 |
C65—C64—C641 | 120.2 (4) | H94D—C941—H94E | 109.5 |
C63—C64—C641 | 121.5 (4) | C94—C941—H94F | 109.5 |
C95—C94—C93 | 117.9 (4) | H94A—C941—H94F | 56.3 |
C95—C94—C941 | 119.1 (5) | H94B—C941—H94F | 56.3 |
C93—C94—C941 | 123.0 (5) | H94C—C941—H94F | 141.1 |
C83—C84—C85 | 120.3 (5) | H94D—C941—H94F | 109.5 |
C83—C84—H84 | 119.9 | H94E—C941—H94F | 109.5 |
C85—C84—H84 | 119.9 | C85—C86—C81 | 120.1 (5) |
C15—C14—C13 | 119.3 (4) | C85—C86—H86 | 119.9 |
C15—C14—H14 | 120.3 | C81—C86—H86 | 119.9 |
C13—C14—H14 | 120.3 | C64—C641—H64A | 109.5 |
C44—C45—C46 | 120.0 (4) | C64—C641—H64B | 109.5 |
C44—C45—H45 | 120.0 | H64A—C641—H64B | 109.5 |
C46—C45—H45 | 120.0 | C64—C641—H64C | 109.5 |
C45—C44—C43 | 119.6 (4) | H64A—C641—H64C | 109.5 |
C45—C44—H44 | 120.2 | H64B—C641—H64C | 109.5 |
C43—C44—H44 | 120.2 | C64—C641—H64D | 109.5 |
C63—C62—C61 | 120.8 (3) | H64A—C641—H64D | 141.1 |
C63—C62—H62 | 119.6 | H64B—C641—H64D | 56.3 |
C61—C62—H62 | 119.6 | H64C—C641—H64D | 56.3 |
C34—C33—C32 | 120.3 (3) | C64—C641—H64E | 109.5 |
C34—C33—H33 | 119.9 | H64A—C641—H64E | 56.3 |
C32—C33—H33 | 119.9 | H64B—C641—H64E | 141.1 |
C53—C54—C55 | 118.7 (4) | H64C—C641—H64E | 56.3 |
C53—C54—H54 | 120.7 | H64D—C641—H64E | 109.5 |
C55—C54—H54 | 120.7 | C64—C641—H64F | 109.5 |
C14—C13—C12 | 120.8 (4) | H64A—C641—H64F | 56.3 |
C14—C13—H13 | 119.6 | H64B—C641—H64F | 56.3 |
C12—C13—H13 | 119.6 | H64C—C641—H64F | 141.1 |
C65—C66—C61 | 120.8 (3) | H64D—C641—H64F | 109.5 |
C65—C66—H66 | 119.6 | H64E—C641—H64F | 109.5 |
C61—C66—H66 | 119.6 | Cu2—I3—Cu1 | 66.2 (5) |
C95—C96—C91 | 121.0 (4) | ||
Cu1—I2—Cu2—P3 | −173.20 (4) | C41—P2—C61—C66 | 67.2 (3) |
Cu1—I2—Cu2—I3 | 14.0 (8) | C51—P2—C61—C66 | −40.5 (3) |
Cu1—I2—Cu2—I1 | 19.07 (12) | Cu1—P2—C61—C66 | −169.7 (3) |
Cu1—I1—Cu2—P3 | 174.12 (4) | C22—C21—C26—C25 | 1.6 (6) |
Cu1—I1—Cu2—I3 | 58 (6) | P1—C21—C26—C25 | 170.9 (3) |
Cu1—I1—Cu2—I2 | −18.90 (11) | C81—P3—C91—C96 | −1.2 (3) |
Cu2—I2—Cu1—P2 | 101.10 (4) | C71—P3—C91—C96 | −110.6 (3) |
Cu2—I2—Cu1—P1 | −128.43 (4) | Cu2—P3—C91—C96 | 129.0 (3) |
Cu2—I2—Cu1—I3 | −12.1 (7) | C81—P3—C91—C92 | 176.4 (3) |
Cu2—I2—Cu1—I1 | −16.15 (11) | C71—P3—C91—C92 | 67.0 (3) |
Cu2—I1—Cu1—P2 | −101.86 (7) | Cu2—P3—C91—C92 | −53.4 (3) |
Cu2—I1—Cu1—P1 | 125.57 (7) | C14—C15—C16—C11 | −2.5 (6) |
Cu2—I1—Cu1—I3 | −76 (5) | C12—C11—C16—C15 | 3.0 (5) |
Cu2—I1—Cu1—I2 | 16.15 (10) | P1—C11—C16—C15 | −175.4 (3) |
I3—Cu2—Cu1—P2 | 94.1 (8) | C91—P3—C81—C82 | −80.2 (3) |
I2—Cu2—Cu1—P2 | −100.12 (4) | C71—P3—C81—C82 | 26.9 (4) |
I1—Cu2—Cu1—P2 | 98.64 (12) | Cu2—P3—C81—C82 | 148.2 (3) |
I3—Cu2—Cu1—P1 | −88.4 (8) | C91—P3—C81—C86 | 95.2 (3) |
I2—Cu2—Cu1—P1 | 77.40 (4) | C71—P3—C81—C86 | −157.6 (3) |
I1—Cu2—Cu1—P1 | −83.83 (12) | Cu2—P3—C81—C86 | −36.4 (4) |
I2—Cu2—Cu1—I3 | 165.8 (8) | C36—C31—C32—C33 | 1.2 (6) |
I1—Cu2—Cu1—I3 | 4.5 (8) | P1—C31—C32—C33 | 179.3 (3) |
I3—Cu2—Cu1—I2 | −165.8 (8) | C26—C21—C22—C23 | −2.2 (6) |
I1—Cu2—Cu1—I2 | −161.24 (12) | P1—C21—C22—C23 | −171.2 (3) |
I3—Cu2—Cu1—I1 | −4.5 (8) | C16—C11—C12—C13 | −1.2 (5) |
I2—Cu2—Cu1—I1 | 161.24 (12) | P1—C11—C12—C13 | 177.2 (3) |
P1—Cu1—P2—C61 | −71.29 (14) | C16—C15—C14—C13 | 0.1 (6) |
I3—Cu1—P2—C61 | 163.3 (4) | C41—C46—C45—C44 | 1.6 (6) |
I2—Cu1—P2—C61 | 47.57 (13) | C46—C45—C44—C43 | −0.6 (7) |
I1—Cu1—P2—C61 | 164.99 (15) | C42—C43—C44—C45 | −0.2 (7) |
Cu2—Cu1—P2—C61 | 106.42 (13) | C66—C61—C62—C63 | −0.5 (5) |
P1—Cu1—P2—C41 | 47.54 (13) | P2—C61—C62—C63 | 179.7 (3) |
I3—Cu1—P2—C41 | −77.9 (4) | C35—C34—C33—C32 | −2.1 (6) |
I2—Cu1—P2—C41 | 166.41 (13) | C341—C34—C33—C32 | 178.2 (4) |
I1—Cu1—P2—C41 | −76.17 (16) | C31—C32—C33—C34 | 0.6 (5) |
Cu2—Cu1—P2—C41 | −134.74 (13) | C15—C14—C13—C12 | 1.6 (6) |
P1—Cu1—P2—C51 | 165.29 (12) | C11—C12—C13—C14 | −1.1 (6) |
I3—Cu1—P2—C51 | 39.9 (4) | C62—C61—C66—C65 | 0.0 (5) |
I2—Cu1—P2—C51 | −75.85 (12) | P2—C61—C66—C65 | 179.8 (3) |
I1—Cu1—P2—C51 | 41.57 (15) | C92—C91—C96—C95 | −2.5 (5) |
Cu2—Cu1—P2—C51 | −17.00 (13) | P3—C91—C96—C95 | 175.0 (3) |
P2—Cu1—P1—C11 | 168.14 (12) | C61—C62—C63—C64 | 1.1 (6) |
I3—Cu1—P1—C11 | −69.0 (4) | C65—C64—C63—C62 | −1.0 (6) |
I2—Cu1—P1—C11 | 46.01 (12) | C641—C64—C63—C62 | 178.5 (4) |
I1—Cu1—P1—C11 | −67.51 (14) | C32—C31—C36—C35 | −1.5 (7) |
Cu2—Cu1—P1—C11 | −9.12 (13) | P1—C31—C36—C35 | −179.5 (4) |
P2—Cu1—P1—C21 | 49.40 (13) | C56—C51—C52—C53 | 0.0 (6) |
I3—Cu1—P1—C21 | 172.3 (4) | P2—C51—C52—C53 | −179.9 (3) |
I2—Cu1—P1—C21 | −72.73 (13) | C73—C72—C71—C76 | 1.0 (6) |
I1—Cu1—P1—C21 | 173.76 (14) | C73—C72—C71—P3 | −178.5 (3) |
Cu2—Cu1—P1—C21 | −127.85 (12) | C81—P3—C71—C72 | 103.8 (3) |
P2—Cu1—P1—C31 | −66.91 (15) | C91—P3—C71—C72 | −149.5 (3) |
I3—Cu1—P1—C31 | 56.0 (4) | Cu2—P3—C71—C72 | −22.4 (3) |
I2—Cu1—P1—C31 | 170.96 (14) | C81—P3—C71—C76 | −75.7 (4) |
I1—Cu1—P1—C31 | 57.44 (16) | C91—P3—C71—C76 | 31.0 (4) |
Cu2—Cu1—P1—C31 | 115.84 (14) | Cu2—P3—C71—C76 | 158.1 (3) |
I3—Cu2—P3—C81 | −13.1 (8) | C61—C66—C65—C64 | 0.0 (6) |
I2—Cu2—P3—C81 | 174.51 (13) | C63—C64—C65—C66 | 0.5 (6) |
I1—Cu2—P3—C81 | −18.10 (19) | C641—C64—C65—C66 | −179.0 (4) |
I3—Cu2—P3—C91 | −136.3 (8) | C85—C84—C83—C82 | −2.3 (8) |
I2—Cu2—P3—C91 | 51.32 (14) | C72—C71—C76—C75 | −0.7 (7) |
I1—Cu2—P3—C91 | −141.29 (18) | P3—C71—C76—C75 | 178.8 (4) |
I3—Cu2—P3—C71 | 106.5 (8) | C71—C72—C73—C74 | −1.1 (7) |
I2—Cu2—P3—C71 | −65.93 (13) | C21—C22—C23—C24 | 2.3 (7) |
I1—Cu2—P3—C71 | 101.46 (18) | C22—C23—C24—C25 | −1.8 (7) |
C21—P1—C11—C12 | 143.9 (3) | C46—C41—C42—C43 | 1.0 (6) |
C31—P1—C11—C12 | −108.8 (3) | P2—C41—C42—C43 | 173.7 (3) |
Cu1—P1—C11—C12 | 22.5 (3) | C44—C43—C42—C41 | 0.0 (7) |
C21—P1—C11—C16 | −37.8 (3) | C95—C94—C93—C92 | −2.6 (7) |
C31—P1—C11—C16 | 69.6 (3) | C941—C94—C93—C92 | 175.2 (5) |
Cu1—P1—C11—C16 | −159.2 (2) | C94—C93—C92—C91 | −0.1 (7) |
C61—P2—C41—C42 | 22.6 (4) | C96—C91—C92—C93 | 2.6 (6) |
C51—P2—C41—C42 | 131.4 (3) | P3—C91—C92—C93 | −175.0 (4) |
Cu1—P2—C41—C42 | −103.4 (3) | C72—C73—C74—C75 | 1.0 (8) |
C61—P2—C41—C46 | −164.6 (3) | C93—C94—C95—C96 | 2.7 (7) |
C51—P2—C41—C46 | −55.9 (3) | C941—C94—C95—C96 | −175.2 (4) |
Cu1—P2—C41—C46 | 69.3 (3) | C91—C96—C95—C94 | −0.1 (6) |
C11—P1—C31—C32 | 128.9 (3) | C23—C24—C25—C26 | 1.2 (7) |
C21—P1—C31—C32 | −122.0 (3) | C21—C26—C25—C24 | −1.1 (7) |
Cu1—P1—C31—C32 | −1.8 (3) | C55—C54—C53—C52 | 0.7 (7) |
C11—P1—C31—C36 | −53.1 (4) | C51—C52—C53—C54 | −0.8 (6) |
C21—P1—C31—C36 | 55.9 (4) | C86—C81—C82—C83 | 0.3 (6) |
Cu1—P1—C31—C36 | 176.1 (4) | P3—C81—C82—C83 | 175.6 (3) |
C11—P1—C21—C26 | 150.4 (3) | C84—C83—C82—C81 | 1.0 (7) |
C31—P1—C21—C26 | 41.6 (4) | C73—C74—C75—C76 | −0.8 (9) |
Cu1—P1—C21—C26 | −83.9 (3) | C71—C76—C75—C74 | 0.6 (8) |
C11—P1—C21—C22 | −40.5 (4) | C51—C56—C55—C54 | −0.8 (6) |
C31—P1—C21—C22 | −149.4 (3) | C53—C54—C55—C56 | 0.1 (6) |
Cu1—P1—C21—C22 | 85.2 (3) | C33—C34—C35—C36 | 1.8 (8) |
C42—C41—C46—C45 | −1.8 (6) | C341—C34—C35—C36 | −178.4 (5) |
P2—C41—C46—C45 | −174.7 (3) | C31—C36—C35—C34 | 0.0 (9) |
C61—P2—C51—C56 | −95.7 (3) | C83—C84—C85—C86 | 2.3 (9) |
C41—P2—C51—C56 | 156.2 (3) | C84—C85—C86—C81 | −1.0 (8) |
Cu1—P2—C51—C56 | 33.8 (3) | C82—C81—C86—C85 | −0.3 (7) |
C61—P2—C51—C52 | 84.3 (3) | P3—C81—C86—C85 | −176.0 (4) |
C41—P2—C51—C52 | −23.9 (4) | P3—Cu2—I3—Cu1 | 173.59 (9) |
Cu1—P2—C51—C52 | −146.3 (3) | I2—Cu2—I3—Cu1 | −14.2 (8) |
C52—C51—C56—C55 | 0.7 (5) | I1—Cu2—I3—Cu1 | −119 (6) |
P2—C51—C56—C55 | −179.3 (3) | P2—Cu1—I3—Cu2 | −104.0 (4) |
C41—P2—C61—C62 | −113.0 (3) | P1—Cu1—I3—Cu2 | 123.4 (4) |
C51—P2—C61—C62 | 139.2 (3) | I2—Cu1—I3—Cu2 | 12.3 (7) |
Cu1—P2—C61—C62 | 10.1 (3) | I1—Cu1—I3—Cu2 | 101 (5) |
Experimental details
Crystal data | |
Chemical formula | [Cu2I2(C19H17P)3] |
Mr | 1209.77 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 13.984 (2), 14.092 (5), 16.084 (3) |
α, β, γ (°) | 103.948 (2), 101.743 (3), 117.769 (4) |
V (Å3) | 2531.1 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.19 |
Crystal size (mm) | 0.16 × 0.15 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.721, 0.862 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 44264, 11001, 8657 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.077, 1.03 |
No. of reflections | 11001 |
No. of parameters | 581 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.89, −0.98 |
Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Putz, 2006).
I1—Cu2 | 2.561 (4) | Cu2—P3 | 2.2209 (11) |
I1—Cu1 | 2.747 (4) | Cu2—Cu1 | 2.7807 (9) |
I2—Cu2 | 2.5421 (10) | Cu1—P2 | 2.2562 (12) |
I2—Cu1 | 2.7033 (8) | Cu1—P1 | 2.2601 (12) |
Cu2—I1—Cu1 | 63.07 (9) | Cu2—I2—Cu1 | 63.941 (18) |
The title complex, (I), is an extension of the previously investigated PPh3 (Eller et al., 1977; Liang et al., 1999) and P(4-Tol)3 (Meijboom, 2006) derivatives. The complex forms part of a range of copper(I) complexes with an iodido molecule coordinated to the metal centre. The range of coordination modes in which the iodido moiety can coordinate to the metal range from single to three centered interactions (i.e. cubane structures).
The title complex presents the most commonly observed coordination pattern for iodido copper(I) complexes, with two distinct copper(I) centres linked via an iodido bridge, see Fig. 1. Compared to previously published structures of the PPh3 (Eller et al., 1977; Liang et al., 1999) and P(4-Tol)3 (Meijboom, 2006) complexes no significant structural effect could be observed when one of the aryl substituents is functionalized. There are no significant intercalation or stacking interactions in the title compound.