metal-organic compounds
Di-μ-iodo-1κI:2κI-tris(tri-m-tolylphosphine)-1κ2P,P′:2κP′′-dicopper(I): a new polymorph
aSchool of Chemistry, Cardiff University, Main Building, Cardiff CF10 3AT, Wales, and bDepartment of Chemistry, King Fahd University of Petroleum and Minerals, PO Box 5048, Dhahran 31261, Saudi Arabia
*Correspondence e-mail: acsbd@yahoo.com
The structure of the title compound, [Cu2I2(C21H21P)3], was redetermined at low temperature (150 K) and shown to be a new triclinic polymorph.
Comment
The title compound, (I), is a binuclear copper(I) complex, in which the Cu atoms are bridged by two I atoms. A total of three molecules of tri-m-tolylphosphine are coordinated to the two copper centres. The structure of the same compound was reported by Akrivos et al. (1993) and shown also to be triclinic, P. This polymorph, (II), has a significantly longer c axis [24.635 Å compared to 19.0630 (3) Å for the present structure, (I)] and slightly smaller cell angles, considering the reduced cells of both polymorphs.
The molecular structure of (I) is illustrated in Fig. 1 and selected bond distances and angles are given in Table 1. In (I), atom Cu1 is coordinated by one P atom (P1), and atom Cu2 is coordinated by two P atoms (P2 and P3). The copper centres are bridged by two I atoms. The intramolecular Cu⋯Cu distance of 2.9551 (4) Å is decreased by ca 0.05 Å compared with that in (II). An interesting difference between the two polymorphs is that the Cu—I distances are inverted. That is, in (I), the Cu1—I distances average 2.5544 (1) Å and the Cu2—I distances average 2.750 (1) Å. This is exactly the opposite situation in polymorph (II) where the corresponding average distances are 2.767 and 2.549 Å, respectively. The Cu—I—Cu angles are very similar. The dihedral angle between the Cu1/I1/I2 and Cu2/I1/I2 planes of 3.75 (12)° is smaller than the value of 8.56° in polymorph (II).
Experimental
A suspension of tri-m-tolylphosphine (0.310 g, 1 mmol) and copper(I) iodide (0.382 g, 2 mmol) in 2-propanol (50 ml) was refluxed for 16 h. The resulting solution was filtered while hot. Slow evaporation of the solvent at room temperature gave colourless crystals of (I).
Crystal data
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Refinement
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The H atoms were placed in calculated positions (aromatic C—H = 0.95 Å and methyl C—H = 0.98 Å), and refined using a riding model, with Uiso(H) = 1.2Ueq(aromatic C) and 1.5Ueq(methyl C). The deepest electron-density hole lies 0.86 Å from atom I2.
Data collection: COLLECT (Nonius, 2000); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536805036925/su6222sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805036925/su6222Isup2.hkl
Data collection: COLLECT (Nonius, 2000); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).[Cu2I2(C21H21P)3] | Z = 2 |
Mr = 1293.92 | F(000) = 1300 |
Triclinic, P1 | Dx = 1.499 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6770 (1) Å | Cell parameters from 12975 reflections |
b = 13.5461 (1) Å | θ = 2.9–27.5° |
c = 19.0630 (3) Å | µ = 1.94 mm−1 |
α = 86.0220 (5)° | T = 150 K |
β = 86.1216 (5)° | Prism, colourless |
γ = 72.6081 (5)° | 0.20 × 0.15 × 0.15 mm |
V = 2867.07 (6) Å3 |
Nonius KappaCCD diffractometer | 12975 independent reflections |
Radiation source: fine-focus sealed tube | 11475 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω scans | θmax = 27.6°, θmin = 3.0° |
Absorption correction: multi-scan (Blessing, 1995) | h = −15→15 |
Tmin = 0.690, Tmax = 0.749 | k = −17→17 |
40258 measured reflections | l = −24→24 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0251P)2 + 3.1211P] where P = (Fo2 + 2Fc2)/3 |
12975 reflections | (Δ/σ)max = 0.002 |
640 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −1.18 e Å−3 |
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 | ||
Cu1 | 0.02400 (3) | 0.68868 (2) | 0.222661 (17) | 0.02206 (7) | |
Cu2 | 0.18389 (3) | 0.47977 (2) | 0.259583 (15) | 0.01785 (7) | |
I1 | 0.227543 (14) | 0.621073 (12) | 0.158303 (8) | 0.02103 (5) | |
I2 | −0.043049 (14) | 0.570632 (12) | 0.315865 (8) | 0.02136 (5) | |
P1 | −0.11002 (6) | 0.84307 (5) | 0.20347 (3) | 0.01869 (13) | |
P2 | 0.18148 (5) | 0.34616 (4) | 0.19479 (3) | 0.01582 (12) | |
P3 | 0.29469 (5) | 0.48396 (5) | 0.35232 (3) | 0.01645 (12) | |
C1 | −0.2436 (2) | 0.83248 (18) | 0.16363 (13) | 0.0198 (5) | |
C2 | −0.3266 (2) | 0.7964 (2) | 0.20524 (15) | 0.0283 (6) | |
H2 | −0.3144 | 0.7807 | 0.2540 | 0.034* | |
C3 | −0.4274 (3) | 0.7826 (2) | 0.17687 (16) | 0.0320 (6) | |
C4 | −0.4430 (2) | 0.8056 (2) | 0.10510 (16) | 0.0298 (6) | |
H4 | −0.5118 | 0.7977 | 0.0850 | 0.036* | |
C5 | −0.3608 (2) | 0.8396 (2) | 0.06292 (15) | 0.0277 (6) | |
H5 | −0.3725 | 0.8538 | 0.0140 | 0.033* | |
C6 | −0.2601 (2) | 0.8534 (2) | 0.09170 (14) | 0.0239 (5) | |
H6 | −0.2032 | 0.8768 | 0.0625 | 0.029* | |
C7 | −0.0631 (2) | 0.94051 (19) | 0.14778 (13) | 0.0212 (5) | |
C8 | 0.0591 (2) | 0.9217 (2) | 0.13164 (14) | 0.0231 (5) | |
H8 | 0.1136 | 0.8579 | 0.1473 | 0.028* | |
C9 | 0.1032 (2) | 0.9950 (2) | 0.09279 (14) | 0.0260 (5) | |
C10 | 0.0222 (3) | 1.0862 (2) | 0.06877 (14) | 0.0271 (6) | |
H10 | 0.0507 | 1.1358 | 0.0410 | 0.033* | |
C11 | −0.1000 (3) | 1.1064 (2) | 0.08466 (15) | 0.0301 (6) | |
H11 | −0.1545 | 1.1696 | 0.0681 | 0.036* | |
C12 | −0.1426 (2) | 1.0346 (2) | 0.12452 (15) | 0.0264 (6) | |
H12 | −0.2262 | 1.0493 | 0.1362 | 0.032* | |
C13 | −0.1705 (2) | 0.91254 (19) | 0.28297 (13) | 0.0209 (5) | |
C14 | −0.2815 (3) | 0.9893 (2) | 0.28606 (14) | 0.0281 (6) | |
H14 | −0.3308 | 1.0025 | 0.2468 | 0.034* | |
C15 | −0.3212 (3) | 1.0467 (2) | 0.34530 (15) | 0.0300 (6) | |
C16 | −0.2471 (3) | 1.0253 (2) | 0.40261 (15) | 0.0329 (6) | |
H16 | −0.2724 | 1.0637 | 0.4436 | 0.039* | |
C17 | −0.1380 (3) | 0.9494 (2) | 0.40034 (15) | 0.0341 (7) | |
H17 | −0.0889 | 0.9361 | 0.4397 | 0.041* | |
C18 | −0.0991 (2) | 0.8920 (2) | 0.34097 (14) | 0.0269 (6) | |
H18 | −0.0242 | 0.8391 | 0.3400 | 0.032* | |
C19 | 0.1394 (2) | 0.24248 (18) | 0.24624 (13) | 0.0180 (5) | |
C20 | 0.2018 (2) | 0.20238 (19) | 0.30726 (13) | 0.0213 (5) | |
H20 | 0.2592 | 0.2329 | 0.3218 | 0.026* | |
C21 | 0.1811 (2) | 0.11864 (19) | 0.34683 (14) | 0.0243 (5) | |
C22 | 0.0925 (3) | 0.0782 (2) | 0.32641 (15) | 0.0269 (6) | |
H22 | 0.0764 | 0.0217 | 0.3533 | 0.032* | |
C23 | 0.0276 (3) | 0.1189 (2) | 0.26755 (16) | 0.0287 (6) | |
H23 | −0.0332 | 0.0911 | 0.2548 | 0.034* | |
C24 | 0.0515 (2) | 0.20046 (19) | 0.22717 (14) | 0.0243 (5) | |
H24 | 0.0077 | 0.2277 | 0.1864 | 0.029* | |
C25 | 0.3255 (2) | 0.27565 (18) | 0.15097 (13) | 0.0185 (5) | |
C26 | 0.3856 (2) | 0.33232 (19) | 0.10718 (13) | 0.0226 (5) | |
H26 | 0.3516 | 0.4053 | 0.1016 | 0.027* | |
C27 | 0.4941 (2) | 0.2855 (2) | 0.07115 (14) | 0.0250 (5) | |
C28 | 0.5417 (2) | 0.1781 (2) | 0.08010 (14) | 0.0268 (6) | |
H28 | 0.6153 | 0.1441 | 0.0558 | 0.032* | |
C29 | 0.4840 (2) | 0.1204 (2) | 0.12348 (14) | 0.0265 (6) | |
H29 | 0.5185 | 0.0475 | 0.1292 | 0.032* | |
C30 | 0.3752 (2) | 0.16838 (19) | 0.15912 (14) | 0.0234 (5) | |
H30 | 0.3352 | 0.1283 | 0.1887 | 0.028* | |
C31 | 0.0775 (2) | 0.37619 (17) | 0.12307 (13) | 0.0182 (5) | |
C32 | −0.0362 (2) | 0.44460 (19) | 0.13600 (13) | 0.0222 (5) | |
H32 | −0.0546 | 0.4772 | 0.1796 | 0.027* | |
C33 | −0.1240 (2) | 0.4663 (2) | 0.08607 (14) | 0.0255 (6) | |
C34 | −0.0950 (3) | 0.4191 (2) | 0.02232 (15) | 0.0277 (6) | |
H34 | −0.1538 | 0.4327 | −0.0121 | 0.033* | |
C35 | 0.0187 (3) | 0.3524 (2) | 0.00824 (14) | 0.0275 (6) | |
H35 | 0.0375 | 0.3214 | −0.0359 | 0.033* | |
C36 | 0.1053 (2) | 0.33065 (19) | 0.05824 (13) | 0.0229 (5) | |
H36 | 0.1831 | 0.2849 | 0.0483 | 0.027* | |
C37 | 0.2461 (2) | 0.60925 (19) | 0.39297 (13) | 0.0197 (5) | |
C38 | 0.2003 (2) | 0.6222 (2) | 0.46267 (14) | 0.0253 (5) | |
H38 | 0.1951 | 0.5635 | 0.4916 | 0.030* | |
C39 | 0.1622 (2) | 0.7206 (2) | 0.49025 (15) | 0.0294 (6) | |
C40 | 0.1715 (2) | 0.8049 (2) | 0.44737 (16) | 0.0305 (6) | |
H40 | 0.1461 | 0.8719 | 0.4656 | 0.037* | |
C41 | 0.2171 (2) | 0.7934 (2) | 0.37836 (16) | 0.0288 (6) | |
H41 | 0.2236 | 0.8521 | 0.3499 | 0.035* | |
C42 | 0.2533 (2) | 0.69572 (19) | 0.35087 (14) | 0.0236 (5) | |
H42 | 0.2830 | 0.6880 | 0.3033 | 0.028* | |
C43 | 0.2905 (2) | 0.39208 (18) | 0.42685 (13) | 0.0194 (5) | |
C44 | 0.3925 (2) | 0.33842 (19) | 0.46361 (13) | 0.0222 (5) | |
H44 | 0.4681 | 0.3478 | 0.4490 | 0.027* | |
C45 | 0.3844 (3) | 0.2713 (2) | 0.52159 (14) | 0.0269 (6) | |
C46 | 0.2734 (3) | 0.2609 (2) | 0.54365 (14) | 0.0297 (6) | |
H46 | 0.2666 | 0.2173 | 0.5840 | 0.036* | |
C47 | 0.1710 (3) | 0.3134 (2) | 0.50753 (15) | 0.0315 (6) | |
H47 | 0.0952 | 0.3054 | 0.5232 | 0.038* | |
C48 | 0.1800 (2) | 0.3773 (2) | 0.44865 (14) | 0.0254 (5) | |
H48 | 0.1108 | 0.4111 | 0.4231 | 0.031* | |
C49 | 0.4546 (2) | 0.46600 (18) | 0.33277 (13) | 0.0197 (5) | |
C50 | 0.5121 (2) | 0.4002 (2) | 0.27961 (14) | 0.0225 (5) | |
H50 | 0.4666 | 0.3686 | 0.2540 | 0.027* | |
C51 | 0.6352 (2) | 0.3798 (2) | 0.26323 (15) | 0.0271 (6) | |
C52 | 0.6989 (2) | 0.4300 (2) | 0.29944 (16) | 0.0312 (6) | |
H52 | 0.7821 | 0.4187 | 0.2880 | 0.037* | |
C53 | 0.6430 (2) | 0.4965 (2) | 0.35200 (17) | 0.0323 (6) | |
H53 | 0.6880 | 0.5303 | 0.3761 | 0.039* | |
C54 | 0.5215 (2) | 0.5139 (2) | 0.36954 (15) | 0.0271 (6) | |
H54 | 0.4839 | 0.5580 | 0.4063 | 0.033* | |
C55 | −0.5157 (3) | 0.7432 (4) | 0.2231 (2) | 0.0585 (11) | |
H55A | −0.4722 | 0.6821 | 0.2516 | 0.088* | |
H55B | −0.5708 | 0.7244 | 0.1937 | 0.088* | |
H55C | −0.5616 | 0.7974 | 0.2542 | 0.088* | |
C56 | 0.2361 (3) | 0.9739 (3) | 0.07822 (19) | 0.0426 (8) | |
H56A | 0.2563 | 1.0393 | 0.0759 | 0.064* | |
H56B | 0.2596 | 0.9407 | 0.0332 | 0.064* | |
H56C | 0.2792 | 0.9279 | 0.1160 | 0.064* | |
C57 | −0.4407 (3) | 1.1296 (3) | 0.34772 (19) | 0.0551 (10) | |
H57A | −0.4822 | 1.1301 | 0.3046 | 0.083* | |
H57B | −0.4278 | 1.1972 | 0.3514 | 0.083* | |
H57C | −0.4899 | 1.1153 | 0.3887 | 0.083* | |
C58 | 0.2519 (3) | 0.0731 (2) | 0.41054 (17) | 0.0416 (8) | |
H58A | 0.3213 | 0.0152 | 0.3969 | 0.062* | |
H58B | 0.2007 | 0.0481 | 0.4459 | 0.062* | |
H58C | 0.2796 | 0.1263 | 0.4303 | 0.062* | |
C59 | 0.5570 (3) | 0.3484 (3) | 0.02395 (18) | 0.0385 (7) | |
H59A | 0.5100 | 0.3758 | −0.0175 | 0.058* | |
H59B | 0.6368 | 0.3044 | 0.0090 | 0.058* | |
H59C | 0.5654 | 0.4059 | 0.0496 | 0.058* | |
C60 | −0.2461 (3) | 0.5430 (2) | 0.10116 (18) | 0.0379 (7) | |
H60A | −0.2386 | 0.5924 | 0.1344 | 0.057* | |
H60B | −0.3016 | 0.5058 | 0.1216 | 0.057* | |
H60C | −0.2770 | 0.5803 | 0.0572 | 0.057* | |
C61 | 0.1116 (3) | 0.7333 (3) | 0.56531 (17) | 0.0474 (9) | |
H61A | 0.1730 | 0.7411 | 0.5953 | 0.071* | |
H61B | 0.0874 | 0.6721 | 0.5821 | 0.071* | |
H61C | 0.0415 | 0.7950 | 0.5673 | 0.071* | |
C62 | 0.4954 (3) | 0.2123 (3) | 0.55996 (18) | 0.0446 (8) | |
H62A | 0.4802 | 0.2219 | 0.6106 | 0.067* | |
H62B | 0.5626 | 0.2384 | 0.5429 | 0.067* | |
H62C | 0.5155 | 0.1385 | 0.5513 | 0.067* | |
C63 | 0.6979 (3) | 0.3029 (3) | 0.20892 (18) | 0.0413 (8) | |
H63A | 0.7559 | 0.3297 | 0.1801 | 0.062* | |
H63B | 0.6384 | 0.2923 | 0.1787 | 0.062* | |
H63C | 0.7402 | 0.2369 | 0.2327 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.01968 (15) | 0.01962 (15) | 0.02568 (17) | −0.00387 (12) | −0.00322 (12) | 0.00026 (12) |
Cu2 | 0.01795 (14) | 0.01681 (14) | 0.01847 (15) | −0.00368 (11) | −0.00283 (11) | −0.00348 (11) |
I1 | 0.02303 (9) | 0.01757 (8) | 0.02112 (8) | −0.00433 (6) | 0.00092 (6) | −0.00102 (6) |
I2 | 0.01693 (8) | 0.02201 (8) | 0.02323 (9) | −0.00336 (6) | 0.00141 (6) | −0.00133 (6) |
P1 | 0.0156 (3) | 0.0181 (3) | 0.0212 (3) | −0.0033 (2) | −0.0020 (2) | 0.0004 (2) |
P2 | 0.0165 (3) | 0.0140 (3) | 0.0158 (3) | −0.0024 (2) | −0.0021 (2) | −0.0013 (2) |
P3 | 0.0150 (3) | 0.0169 (3) | 0.0170 (3) | −0.0035 (2) | −0.0018 (2) | −0.0030 (2) |
C1 | 0.0179 (11) | 0.0183 (11) | 0.0217 (12) | −0.0026 (9) | −0.0019 (9) | −0.0031 (9) |
C2 | 0.0273 (14) | 0.0367 (15) | 0.0240 (14) | −0.0139 (12) | −0.0036 (11) | 0.0000 (11) |
C3 | 0.0280 (14) | 0.0401 (16) | 0.0310 (15) | −0.0146 (13) | −0.0012 (12) | −0.0036 (12) |
C4 | 0.0227 (13) | 0.0302 (14) | 0.0357 (16) | −0.0038 (11) | −0.0075 (11) | −0.0092 (12) |
C5 | 0.0280 (14) | 0.0292 (14) | 0.0245 (13) | −0.0046 (11) | −0.0069 (11) | −0.0040 (11) |
C6 | 0.0236 (13) | 0.0235 (12) | 0.0229 (13) | −0.0042 (10) | −0.0002 (10) | −0.0033 (10) |
C7 | 0.0247 (12) | 0.0196 (11) | 0.0186 (12) | −0.0053 (10) | −0.0012 (10) | −0.0016 (9) |
C8 | 0.0221 (12) | 0.0207 (12) | 0.0261 (13) | −0.0051 (10) | −0.0005 (10) | −0.0035 (10) |
C9 | 0.0287 (14) | 0.0273 (13) | 0.0234 (13) | −0.0101 (11) | 0.0011 (11) | −0.0046 (10) |
C10 | 0.0400 (16) | 0.0219 (12) | 0.0215 (13) | −0.0133 (12) | 0.0008 (11) | 0.0012 (10) |
C11 | 0.0353 (15) | 0.0201 (12) | 0.0323 (15) | −0.0036 (11) | −0.0056 (12) | 0.0007 (11) |
C12 | 0.0242 (13) | 0.0219 (12) | 0.0297 (14) | −0.0017 (11) | −0.0033 (11) | 0.0011 (10) |
C13 | 0.0203 (12) | 0.0206 (12) | 0.0229 (13) | −0.0078 (10) | −0.0025 (10) | 0.0009 (10) |
C14 | 0.0285 (14) | 0.0285 (14) | 0.0231 (13) | −0.0015 (11) | −0.0049 (11) | −0.0006 (11) |
C15 | 0.0320 (15) | 0.0255 (13) | 0.0272 (14) | −0.0010 (12) | 0.0017 (11) | −0.0018 (11) |
C16 | 0.0426 (17) | 0.0374 (15) | 0.0214 (14) | −0.0157 (14) | 0.0031 (12) | −0.0080 (11) |
C17 | 0.0341 (15) | 0.0475 (17) | 0.0236 (14) | −0.0151 (14) | −0.0070 (12) | −0.0036 (12) |
C18 | 0.0221 (13) | 0.0346 (14) | 0.0247 (13) | −0.0093 (11) | −0.0032 (10) | 0.0007 (11) |
C19 | 0.0188 (11) | 0.0151 (11) | 0.0189 (12) | −0.0030 (9) | 0.0008 (9) | −0.0028 (9) |
C20 | 0.0250 (12) | 0.0214 (12) | 0.0182 (12) | −0.0075 (10) | −0.0030 (10) | −0.0016 (9) |
C21 | 0.0296 (14) | 0.0202 (12) | 0.0203 (12) | −0.0034 (11) | 0.0010 (10) | −0.0011 (10) |
C22 | 0.0324 (14) | 0.0193 (12) | 0.0283 (14) | −0.0085 (11) | 0.0068 (11) | −0.0008 (10) |
C23 | 0.0274 (14) | 0.0253 (13) | 0.0368 (16) | −0.0121 (11) | −0.0038 (11) | −0.0030 (11) |
C24 | 0.0259 (13) | 0.0212 (12) | 0.0266 (13) | −0.0071 (11) | −0.0068 (10) | −0.0004 (10) |
C25 | 0.0180 (11) | 0.0191 (11) | 0.0171 (11) | −0.0024 (9) | −0.0034 (9) | −0.0041 (9) |
C26 | 0.0215 (12) | 0.0204 (12) | 0.0236 (13) | −0.0025 (10) | −0.0004 (10) | −0.0039 (10) |
C27 | 0.0192 (12) | 0.0332 (14) | 0.0230 (13) | −0.0075 (11) | −0.0010 (10) | −0.0048 (11) |
C28 | 0.0172 (12) | 0.0347 (14) | 0.0219 (13) | 0.0039 (11) | −0.0012 (10) | −0.0087 (11) |
C29 | 0.0257 (13) | 0.0213 (12) | 0.0253 (13) | 0.0051 (11) | −0.0039 (11) | −0.0032 (10) |
C30 | 0.0245 (13) | 0.0198 (12) | 0.0228 (13) | −0.0013 (10) | −0.0031 (10) | −0.0013 (10) |
C31 | 0.0233 (12) | 0.0133 (10) | 0.0178 (11) | −0.0048 (9) | −0.0040 (9) | 0.0005 (9) |
C32 | 0.0244 (13) | 0.0221 (12) | 0.0193 (12) | −0.0043 (10) | −0.0052 (10) | −0.0022 (9) |
C33 | 0.0237 (13) | 0.0220 (12) | 0.0297 (14) | −0.0044 (11) | −0.0087 (11) | 0.0022 (10) |
C34 | 0.0335 (15) | 0.0241 (13) | 0.0260 (14) | −0.0074 (11) | −0.0144 (11) | 0.0028 (10) |
C35 | 0.0401 (16) | 0.0248 (13) | 0.0173 (12) | −0.0078 (12) | −0.0059 (11) | −0.0035 (10) |
C36 | 0.0283 (13) | 0.0181 (11) | 0.0203 (12) | −0.0030 (10) | −0.0037 (10) | −0.0028 (9) |
C37 | 0.0138 (11) | 0.0225 (12) | 0.0229 (12) | −0.0035 (9) | −0.0049 (9) | −0.0052 (10) |
C38 | 0.0227 (13) | 0.0267 (13) | 0.0241 (13) | −0.0021 (11) | −0.0025 (10) | −0.0067 (10) |
C39 | 0.0234 (13) | 0.0326 (14) | 0.0288 (14) | 0.0006 (11) | −0.0058 (11) | −0.0136 (11) |
C40 | 0.0223 (13) | 0.0234 (13) | 0.0435 (17) | 0.0013 (11) | −0.0092 (12) | −0.0155 (12) |
C41 | 0.0287 (14) | 0.0204 (12) | 0.0376 (16) | −0.0058 (11) | −0.0095 (12) | −0.0035 (11) |
C42 | 0.0221 (12) | 0.0231 (12) | 0.0264 (13) | −0.0063 (10) | −0.0050 (10) | −0.0041 (10) |
C43 | 0.0211 (12) | 0.0173 (11) | 0.0184 (12) | −0.0025 (10) | −0.0026 (9) | −0.0040 (9) |
C44 | 0.0214 (12) | 0.0225 (12) | 0.0217 (12) | −0.0037 (10) | −0.0029 (10) | −0.0032 (10) |
C45 | 0.0314 (14) | 0.0244 (13) | 0.0221 (13) | −0.0026 (11) | −0.0063 (11) | −0.0015 (10) |
C46 | 0.0398 (16) | 0.0301 (14) | 0.0198 (13) | −0.0118 (12) | −0.0029 (11) | 0.0026 (11) |
C47 | 0.0294 (14) | 0.0389 (16) | 0.0279 (15) | −0.0134 (13) | −0.0007 (11) | 0.0005 (12) |
C48 | 0.0225 (12) | 0.0295 (13) | 0.0242 (13) | −0.0076 (11) | −0.0035 (10) | 0.0018 (10) |
C49 | 0.0175 (11) | 0.0187 (11) | 0.0220 (12) | −0.0040 (9) | −0.0018 (9) | 0.0003 (9) |
C50 | 0.0180 (12) | 0.0247 (12) | 0.0246 (13) | −0.0057 (10) | −0.0019 (10) | −0.0026 (10) |
C51 | 0.0170 (12) | 0.0336 (14) | 0.0286 (14) | −0.0046 (11) | 0.0002 (10) | −0.0023 (11) |
C52 | 0.0167 (12) | 0.0423 (16) | 0.0342 (16) | −0.0080 (12) | −0.0018 (11) | −0.0026 (12) |
C53 | 0.0216 (13) | 0.0373 (15) | 0.0413 (17) | −0.0115 (12) | −0.0054 (12) | −0.0081 (13) |
C54 | 0.0214 (13) | 0.0298 (14) | 0.0298 (14) | −0.0054 (11) | −0.0015 (11) | −0.0088 (11) |
C55 | 0.046 (2) | 0.104 (3) | 0.044 (2) | −0.051 (2) | −0.0043 (16) | 0.003 (2) |
C56 | 0.0286 (15) | 0.0477 (19) | 0.052 (2) | −0.0152 (14) | 0.0056 (14) | 0.0049 (15) |
C57 | 0.054 (2) | 0.050 (2) | 0.0401 (19) | 0.0180 (18) | 0.0011 (16) | −0.0104 (16) |
C58 | 0.060 (2) | 0.0352 (16) | 0.0309 (16) | −0.0160 (16) | −0.0163 (15) | 0.0131 (13) |
C59 | 0.0325 (16) | 0.0418 (17) | 0.0397 (18) | −0.0117 (14) | 0.0107 (13) | −0.0016 (14) |
C60 | 0.0269 (15) | 0.0383 (16) | 0.0429 (18) | 0.0019 (13) | −0.0136 (13) | −0.0050 (14) |
C61 | 0.055 (2) | 0.0480 (19) | 0.0313 (17) | −0.0004 (17) | 0.0033 (15) | −0.0199 (15) |
C62 | 0.0409 (18) | 0.0473 (19) | 0.0396 (18) | −0.0045 (15) | −0.0161 (15) | 0.0151 (15) |
C63 | 0.0239 (14) | 0.053 (2) | 0.0442 (19) | −0.0048 (14) | 0.0050 (13) | −0.0191 (15) |
Cu1—Cu2 | 2.9551 (4) | C30—H30 | 0.9500 |
Cu1—P1 | 2.2298 (7) | C31—C32 | 1.391 (3) |
Cu2—P2 | 2.2687 (7) | C31—C36 | 1.395 (3) |
Cu1—I1 | 2.5403 (3) | C32—C33 | 1.399 (3) |
Cu1—I2 | 2.5481 (4) | C32—H32 | 0.9500 |
Cu1—Cu2 | 2.9551 (4) | C33—C34 | 1.387 (4) |
Cu2—P3 | 2.2737 (7) | C33—C60 | 1.514 (4) |
Cu2—I2 | 2.7454 (3) | C34—C35 | 1.385 (4) |
Cu2—I1 | 2.7548 (3) | C34—H34 | 0.9500 |
P1—C7 | 1.824 (3) | C35—C36 | 1.390 (4) |
P1—C13 | 1.827 (3) | C35—H35 | 0.9500 |
P1—C1 | 1.827 (3) | C36—H36 | 0.9500 |
P2—C19 | 1.825 (3) | C37—C42 | 1.394 (4) |
P2—C31 | 1.833 (2) | C37—C38 | 1.401 (4) |
P2—C25 | 1.844 (2) | C38—C39 | 1.401 (4) |
P3—C49 | 1.826 (3) | C38—H38 | 0.9500 |
P3—C37 | 1.830 (2) | C39—C40 | 1.384 (4) |
P3—C43 | 1.831 (3) | C39—C61 | 1.512 (4) |
C1—C2 | 1.391 (4) | C40—C41 | 1.387 (4) |
C1—C6 | 1.395 (4) | C40—H40 | 0.9500 |
C2—C3 | 1.394 (4) | C41—C42 | 1.391 (4) |
C2—H2 | 0.9500 | C41—H41 | 0.9500 |
C3—C4 | 1.394 (4) | C42—H42 | 0.9500 |
C3—C55 | 1.505 (5) | C43—C48 | 1.396 (4) |
C4—C5 | 1.375 (4) | C43—C44 | 1.401 (3) |
C4—H4 | 0.9500 | C44—C45 | 1.399 (4) |
C5—C6 | 1.397 (4) | C44—H44 | 0.9500 |
C5—H5 | 0.9500 | C45—C46 | 1.380 (4) |
C6—H6 | 0.9500 | C45—C62 | 1.511 (4) |
C7—C8 | 1.389 (4) | C46—C47 | 1.394 (4) |
C7—C12 | 1.398 (3) | C46—H46 | 0.9500 |
C8—C9 | 1.396 (4) | C47—C48 | 1.387 (4) |
C8—H8 | 0.9500 | C47—H47 | 0.9500 |
C9—C10 | 1.383 (4) | C48—H48 | 0.9500 |
C9—C56 | 1.502 (4) | C49—C50 | 1.395 (3) |
C10—C11 | 1.387 (4) | C49—C54 | 1.401 (4) |
C10—H10 | 0.9500 | C50—C51 | 1.399 (4) |
C11—C12 | 1.380 (4) | C50—H50 | 0.9500 |
C11—H11 | 0.9500 | C51—C52 | 1.388 (4) |
C12—H12 | 0.9500 | C51—C63 | 1.511 (4) |
C13—C18 | 1.393 (4) | C52—C53 | 1.388 (4) |
C13—C14 | 1.399 (4) | C52—H52 | 0.9500 |
C14—C15 | 1.389 (4) | C53—C54 | 1.388 (4) |
C14—H14 | 0.9500 | C53—H53 | 0.9500 |
C15—C16 | 1.400 (4) | C54—H54 | 0.9500 |
C15—C57 | 1.507 (4) | C55—H55A | 0.9800 |
C16—C17 | 1.378 (4) | C55—H55B | 0.9800 |
C16—H16 | 0.9500 | C55—H55C | 0.9800 |
C17—C18 | 1.390 (4) | C56—H56A | 0.9800 |
C17—H17 | 0.9500 | C56—H56B | 0.9800 |
C18—H18 | 0.9500 | C56—H56C | 0.9800 |
C19—C24 | 1.392 (4) | C57—H57A | 0.9800 |
C19—C20 | 1.404 (3) | C57—H57B | 0.9800 |
C20—C21 | 1.391 (4) | C57—H57C | 0.9800 |
C20—H20 | 0.9500 | C58—H58A | 0.9800 |
C21—C22 | 1.394 (4) | C58—H58B | 0.9800 |
C21—C58 | 1.505 (4) | C58—H58C | 0.9800 |
C22—C23 | 1.385 (4) | C59—H59A | 0.9800 |
C22—H22 | 0.9500 | C59—H59B | 0.9800 |
C23—C24 | 1.388 (4) | C59—H59C | 0.9800 |
C23—H23 | 0.9500 | C60—H60A | 0.9800 |
C24—H24 | 0.9500 | C60—H60B | 0.9800 |
C25—C26 | 1.390 (4) | C60—H60C | 0.9800 |
C25—C30 | 1.396 (3) | C61—H61A | 0.9800 |
C26—C27 | 1.394 (4) | C61—H61B | 0.9800 |
C26—H26 | 0.9500 | C61—H61C | 0.9800 |
C27—C28 | 1.396 (4) | C62—H62A | 0.9800 |
C27—C59 | 1.501 (4) | C62—H62B | 0.9800 |
C28—C29 | 1.378 (4) | C62—H62C | 0.9800 |
C28—H28 | 0.9500 | C63—H63A | 0.9800 |
C29—C30 | 1.397 (4) | C63—H63B | 0.9800 |
C29—H29 | 0.9500 | C63—H63C | 0.9800 |
P1—Cu1—I1 | 126.33 (2) | C32—C31—C36 | 119.2 (2) |
P1—Cu1—I2 | 114.78 (2) | C32—C31—P2 | 117.46 (18) |
I1—Cu1—I2 | 118.859 (12) | C36—C31—P2 | 123.32 (19) |
P1—Cu1—Cu2 | 174.07 (2) | C31—C32—C33 | 121.3 (2) |
I1—Cu1—Cu2 | 59.603 (9) | C31—C32—H32 | 119.3 |
I2—Cu1—Cu2 | 59.302 (9) | C33—C32—H32 | 119.3 |
P2—Cu2—P3 | 130.66 (2) | C34—C33—C32 | 118.5 (2) |
P2—Cu2—I2 | 109.470 (19) | C34—C33—C60 | 121.4 (2) |
P3—Cu2—I2 | 100.138 (19) | C32—C33—C60 | 120.0 (2) |
P2—Cu2—I1 | 102.441 (19) | C35—C34—C33 | 120.7 (2) |
P3—Cu2—I1 | 106.48 (2) | C35—C34—H34 | 119.6 |
I2—Cu2—I1 | 105.603 (10) | C33—C34—H34 | 119.6 |
P2—Cu2—Cu1 | 118.613 (19) | C34—C35—C36 | 120.5 (2) |
P3—Cu2—Cu1 | 110.716 (19) | C34—C35—H35 | 119.8 |
I2—Cu2—Cu1 | 52.948 (9) | C36—C35—H35 | 119.8 |
I1—Cu2—Cu1 | 52.691 (9) | C35—C36—C31 | 119.8 (2) |
Cu1—I1—Cu2 | 67.706 (10) | C35—C36—H36 | 120.1 |
Cu1—I2—Cu2 | 67.750 (10) | C31—C36—H36 | 120.1 |
C7—P1—C13 | 102.16 (11) | C42—C37—C38 | 119.3 (2) |
C7—P1—C1 | 104.81 (12) | C42—C37—P3 | 117.19 (19) |
C13—P1—C1 | 103.52 (11) | C38—C37—P3 | 123.5 (2) |
C7—P1—Cu1 | 118.29 (8) | C37—C38—C39 | 120.8 (3) |
C13—P1—Cu1 | 114.52 (8) | C37—C38—H38 | 119.6 |
C1—P1—Cu1 | 111.95 (8) | C39—C38—H38 | 119.6 |
C19—P2—C31 | 102.78 (11) | C40—C39—C38 | 118.7 (3) |
C19—P2—C25 | 102.26 (11) | C40—C39—C61 | 121.3 (3) |
C31—P2—C25 | 102.94 (11) | C38—C39—C61 | 120.1 (3) |
C19—P2—Cu2 | 113.61 (8) | C39—C40—C41 | 121.3 (2) |
C31—P2—Cu2 | 116.89 (8) | C39—C40—H40 | 119.3 |
C25—P2—Cu2 | 116.38 (8) | C41—C40—H40 | 119.3 |
C49—P3—C37 | 102.41 (11) | C40—C41—C42 | 119.8 (3) |
C49—P3—C43 | 104.20 (11) | C40—C41—H41 | 120.1 |
C37—P3—C43 | 103.00 (11) | C42—C41—H41 | 120.1 |
C49—P3—Cu2 | 116.33 (8) | C41—C42—C37 | 120.1 (3) |
C37—P3—Cu2 | 112.46 (8) | C41—C42—H42 | 119.9 |
C43—P3—Cu2 | 116.65 (8) | C37—C42—H42 | 119.9 |
C2—C1—C6 | 119.4 (2) | C48—C43—C44 | 119.0 (2) |
C2—C1—P1 | 119.05 (19) | C48—C43—P3 | 118.13 (18) |
C6—C1—P1 | 121.4 (2) | C44—C43—P3 | 122.8 (2) |
C1—C2—C3 | 121.4 (3) | C45—C44—C43 | 120.9 (3) |
C1—C2—H2 | 119.3 | C45—C44—H44 | 119.6 |
C3—C2—H2 | 119.3 | C43—C44—H44 | 119.6 |
C2—C3—C4 | 118.2 (3) | C46—C45—C44 | 119.0 (2) |
C2—C3—C55 | 120.3 (3) | C46—C45—C62 | 120.7 (3) |
C4—C3—C55 | 121.5 (3) | C44—C45—C62 | 120.4 (3) |
C5—C4—C3 | 121.2 (3) | C45—C46—C47 | 120.9 (3) |
C5—C4—H4 | 119.4 | C45—C46—H46 | 119.5 |
C3—C4—H4 | 119.4 | C47—C46—H46 | 119.5 |
C4—C5—C6 | 120.3 (3) | C48—C47—C46 | 119.9 (3) |
C4—C5—H5 | 119.9 | C48—C47—H47 | 120.0 |
C6—C5—H5 | 119.9 | C46—C47—H47 | 120.0 |
C1—C6—C5 | 119.5 (3) | C47—C48—C43 | 120.2 (2) |
C1—C6—H6 | 120.2 | C47—C48—H48 | 119.9 |
C5—C6—H6 | 120.2 | C43—C48—H48 | 119.9 |
C8—C7—C12 | 119.0 (2) | C50—C49—C54 | 119.2 (2) |
C8—C7—P1 | 117.51 (19) | C50—C49—P3 | 117.99 (19) |
C12—C7—P1 | 123.4 (2) | C54—C49—P3 | 122.79 (19) |
C7—C8—C9 | 121.2 (2) | C49—C50—C51 | 121.3 (2) |
C7—C8—H8 | 119.4 | C49—C50—H50 | 119.3 |
C9—C8—H8 | 119.4 | C51—C50—H50 | 119.3 |
C10—C9—C8 | 118.6 (3) | C52—C51—C50 | 118.3 (3) |
C10—C9—C56 | 121.5 (3) | C52—C51—C63 | 120.9 (2) |
C8—C9—C56 | 119.9 (3) | C50—C51—C63 | 120.8 (3) |
C9—C10—C11 | 121.0 (3) | C53—C52—C51 | 121.1 (3) |
C9—C10—H10 | 119.5 | C53—C52—H52 | 119.4 |
C11—C10—H10 | 119.5 | C51—C52—H52 | 119.4 |
C12—C11—C10 | 120.1 (2) | C54—C53—C52 | 120.3 (3) |
C12—C11—H11 | 120.0 | C54—C53—H53 | 119.8 |
C10—C11—H11 | 120.0 | C52—C53—H53 | 119.8 |
C11—C12—C7 | 120.2 (3) | C53—C54—C49 | 119.7 (3) |
C11—C12—H12 | 119.9 | C53—C54—H54 | 120.1 |
C7—C12—H12 | 119.9 | C49—C54—H54 | 120.1 |
C18—C13—C14 | 119.3 (2) | C3—C55—H55A | 109.5 |
C18—C13—P1 | 117.98 (19) | C3—C55—H55B | 109.5 |
C14—C13—P1 | 122.60 (19) | H55A—C55—H55B | 109.5 |
C15—C14—C13 | 121.5 (2) | C3—C55—H55C | 109.5 |
C15—C14—H14 | 119.3 | H55A—C55—H55C | 109.5 |
C13—C14—H14 | 119.3 | H55B—C55—H55C | 109.5 |
C14—C15—C16 | 118.1 (3) | C9—C56—H56A | 109.5 |
C14—C15—C57 | 120.9 (3) | C9—C56—H56B | 109.5 |
C16—C15—C57 | 121.0 (3) | H56A—C56—H56B | 109.5 |
C17—C16—C15 | 120.9 (3) | C9—C56—H56C | 109.5 |
C17—C16—H16 | 119.5 | H56A—C56—H56C | 109.5 |
C15—C16—H16 | 119.5 | H56B—C56—H56C | 109.5 |
C16—C17—C18 | 120.6 (3) | C15—C57—H57A | 109.5 |
C16—C17—H17 | 119.7 | C15—C57—H57B | 109.5 |
C18—C17—H17 | 119.7 | H57A—C57—H57B | 109.5 |
C17—C18—C13 | 119.6 (3) | C15—C57—H57C | 109.5 |
C17—C18—H18 | 120.2 | H57A—C57—H57C | 109.5 |
C13—C18—H18 | 120.2 | H57B—C57—H57C | 109.5 |
C24—C19—C20 | 119.1 (2) | C21—C58—H58A | 109.5 |
C24—C19—P2 | 123.49 (19) | C21—C58—H58B | 109.5 |
C20—C19—P2 | 117.40 (19) | H58A—C58—H58B | 109.5 |
C21—C20—C19 | 121.1 (2) | C21—C58—H58C | 109.5 |
C21—C20—H20 | 119.5 | H58A—C58—H58C | 109.5 |
C19—C20—H20 | 119.5 | H58B—C58—H58C | 109.5 |
C20—C21—C22 | 118.5 (2) | C27—C59—H59A | 109.5 |
C20—C21—C58 | 120.9 (3) | C27—C59—H59B | 109.5 |
C22—C21—C58 | 120.7 (3) | H59A—C59—H59B | 109.5 |
C23—C22—C21 | 121.1 (2) | C27—C59—H59C | 109.5 |
C23—C22—H22 | 119.4 | H59A—C59—H59C | 109.5 |
C21—C22—H22 | 119.4 | H59B—C59—H59C | 109.5 |
C22—C23—C24 | 120.0 (3) | C33—C60—H60A | 109.5 |
C22—C23—H23 | 120.0 | C33—C60—H60B | 109.5 |
C24—C23—H23 | 120.0 | H60A—C60—H60B | 109.5 |
C23—C24—C19 | 120.2 (2) | C33—C60—H60C | 109.5 |
C23—C24—H24 | 119.9 | H60A—C60—H60C | 109.5 |
C19—C24—H24 | 119.9 | H60B—C60—H60C | 109.5 |
C26—C25—C30 | 119.1 (2) | C39—C61—H61A | 109.5 |
C26—C25—P2 | 118.06 (18) | C39—C61—H61B | 109.5 |
C30—C25—P2 | 122.8 (2) | H61A—C61—H61B | 109.5 |
C25—C26—C27 | 122.1 (2) | C39—C61—H61C | 109.5 |
C25—C26—H26 | 119.0 | H61A—C61—H61C | 109.5 |
C27—C26—H26 | 119.0 | H61B—C61—H61C | 109.5 |
C26—C27—C28 | 117.7 (3) | C45—C62—H62A | 109.5 |
C26—C27—C59 | 121.1 (3) | C45—C62—H62B | 109.5 |
C28—C27—C59 | 121.2 (2) | H62A—C62—H62B | 109.5 |
C29—C28—C27 | 121.2 (2) | C45—C62—H62C | 109.5 |
C29—C28—H28 | 119.4 | H62A—C62—H62C | 109.5 |
C27—C28—H28 | 119.4 | H62B—C62—H62C | 109.5 |
C28—C29—C30 | 120.5 (2) | C51—C63—H63A | 109.5 |
C28—C29—H29 | 119.8 | C51—C63—H63B | 109.5 |
C30—C29—H29 | 119.8 | H63A—C63—H63B | 109.5 |
C25—C30—C29 | 119.5 (3) | C51—C63—H63C | 109.5 |
C25—C30—H30 | 120.3 | H63A—C63—H63C | 109.5 |
C29—C30—H30 | 120.3 | H63B—C63—H63C | 109.5 |
Acknowledgements
ZSS acknowledges King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia, for financial support.
References
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