metal-organic compounds
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catena-Poly[[copper(I)-bis[μ-bis(diphenylphosphino)methane-κ2P:P′]-copper(I)-μ-2,2′-bipyridine-κ2N:N′] bis(tetrafluoridoborate) dichloromethane 2.5-solvate]
aCollege of Animal Husbandry and Veterinary Studies, Henan Agricultural University, Zhengzhou, Henan Province 450002, People's Republic of China
*Correspondence e-mail: mojuan52@126.com
The title complex, {[Cu2(C10H8N2)(C25H22P2)2](BF4)2·2.5CH2Cl2}n, contains chains of CuI centres bridged alternately by two (diphenylphosphino)methane (dppm) and 4,4′-bipyridine (bpy) ligands. Each CuI atom is coordinated by one N atom of 4,4′-bipyridine (bpy) and two P atoms of two (diphenylphosphino)methane (dppm) ligand, and has a trigonal-planar coordination geometry. There is an inversion centre midway between each pair of adjacent Cu atoms. The distance of two CuI atoms separated by two (diphenylphosphino)methane bridging ligands is 3.732 (3) Å, and 4,4′-bipyridine 11.138 (5) Å.
Related literature
For related literature, see: Ahuja et al. (2007); Liu et al. (2006); Park et al. (2001); Sekabunga et al. (2002); Yam et al. (2001).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808001530/hg2367sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001530/hg2367Isup2.hkl
A 10 ml dichloromethane solution of 4,4'-bipyridine (0.078 g, 0.5 mmol) was added to a 20 mL dichloromethane solution of [Cu(CH3CN)4][BF4] (0.372 g, 1.0 mmol) and (diphenylphosphino)methane (0.384 g, 1.0 mmol) under N2 atmosphere. The mixture was stirred for 10 h. Yellow crystals suitable for X-ray diffraction were formed by vapour diffusion of diethyl ethyl ether into dichloromethane solution.
All hydrogen atoms were generated geometrically (C—H bond lengths fixed at 0.93 Å), assigned appropriated isotropic thermal parameters, Uiso(H) = 1.2Ueq(C). During the structure
a region of electron density was identified as a disordered dichloromethane solvent molecule. The site occupancies were determined using an isotropic model using DFIX 1.75 (1) (C61—Cl1, C61—Cl2, C61—Cl1', C61—Cl2') Å restraints in subsequent cycles. 'ISOR' and 'simu' restraint was applied for atoms from F1 to Cl6 for preventing these atoms from becoming 'non-positive-definite'.Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Cu2(C10H8N2)(C25H22P2)2](BF4)2·2.5CH2Cl2 | Z = 2 |
Mr = 1437.93 | F(000) = 1462 |
Triclinic, P1 | Dx = 1.386 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9860 (12) Å | Cell parameters from 4736 reflections |
b = 16.1541 (18) Å | θ = 2.4–23.6° |
c = 20.336 (2) Å | µ = 0.96 mm−1 |
α = 82.821 (2)° | T = 294 K |
β = 89.030 (2)° | Block, yellow |
γ = 74.237 (2)° | 0.22 × 0.12 × 0.06 mm |
V = 3445.5 (7) Å3 |
Bruker SMART CCD area-detector diffractometer | 12068 independent reflections |
Radiation source: fine-focus sealed tube | 7620 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
phi and ω scans | θmax = 25.0°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.871, Tmax = 0.947 | k = −19→17 |
17673 measured reflections | l = −24→22 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.231 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.1056P)2 + 4.6434P] where P = (Fo2 + 2Fc2)/3 |
12068 reflections | (Δ/σ)max = 0.005 |
802 parameters | Δρmax = 1.14 e Å−3 |
142 restraints | Δρmin = −0.54 e Å−3 |
[Cu2(C10H8N2)(C25H22P2)2](BF4)2·2.5CH2Cl2 | γ = 74.237 (2)° |
Mr = 1437.93 | V = 3445.5 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.9860 (12) Å | Mo Kα radiation |
b = 16.1541 (18) Å | µ = 0.96 mm−1 |
c = 20.336 (2) Å | T = 294 K |
α = 82.821 (2)° | 0.22 × 0.12 × 0.06 mm |
β = 89.030 (2)° |
Bruker SMART CCD area-detector diffractometer | 12068 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7620 reflections with I > 2σ(I) |
Tmin = 0.871, Tmax = 0.947 | Rint = 0.029 |
17673 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 142 restraints |
wR(F2) = 0.231 | H-atom parameters constrained |
S = 1.16 | Δρmax = 1.14 e Å−3 |
12068 reflections | Δρmin = −0.54 e Å−3 |
802 parameters |
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) | |
Cu1 | 0.78585 (7) | 0.65849 (5) | 0.13999 (4) | 0.0383 (2) | |
Cu2 | 0.78806 (7) | 0.65568 (5) | 0.32279 (4) | 0.0428 (2) | |
P1 | 0.98370 (15) | 0.57875 (11) | 0.16926 (8) | 0.0355 (4) | |
P2 | 0.99714 (16) | 0.59589 (11) | 0.32001 (8) | 0.0389 (4) | |
P3 | 0.72735 (15) | 0.80272 (10) | 0.13569 (8) | 0.0366 (4) | |
P4 | 0.67290 (16) | 0.78988 (11) | 0.28283 (8) | 0.0395 (4) | |
N1 | 0.6855 (5) | 0.6018 (4) | 0.0866 (3) | 0.0495 (14) | |
N2 | 0.6907 (5) | 0.5954 (4) | 0.3888 (3) | 0.0525 (15) | |
C1 | 1.0679 (6) | 0.6038 (4) | 0.2380 (3) | 0.0375 (14) | |
H1A | 1.1528 | 0.5650 | 0.2409 | 0.045* | |
H1B | 1.0757 | 0.6623 | 0.2271 | 0.045* | |
C2 | 0.7395 (6) | 0.8469 (4) | 0.2137 (3) | 0.0425 (15) | |
H2A | 0.8277 | 0.8415 | 0.2235 | 0.051* | |
H2B | 0.6947 | 0.9081 | 0.2087 | 0.051* | |
C3 | 0.6815 (7) | 0.6091 (5) | 0.0209 (4) | 0.0549 (19) | |
H3 | 0.7289 | 0.6421 | −0.0028 | 0.066* | |
C4 | 0.6106 (7) | 0.5704 (5) | −0.0141 (4) | 0.0532 (18) | |
H4 | 0.6118 | 0.5775 | −0.0602 | 0.064* | |
C5 | 0.5390 (6) | 0.5220 (4) | 0.0178 (3) | 0.0426 (15) | |
C6 | 0.5439 (9) | 0.5137 (7) | 0.0860 (4) | 0.084 (3) | |
H6 | 0.4981 | 0.4804 | 0.1106 | 0.101* | |
C7 | 0.6158 (9) | 0.5541 (6) | 0.1177 (4) | 0.075 (3) | |
H7 | 0.6158 | 0.5479 | 0.1638 | 0.090* | |
C8 | 0.6417 (9) | 0.5347 (6) | 0.3733 (4) | 0.070 (2) | |
H8 | 0.6570 | 0.5173 | 0.3313 | 0.084* | |
C9 | 0.5684 (9) | 0.4951 (6) | 0.4156 (4) | 0.072 (2) | |
H9 | 0.5372 | 0.4519 | 0.4019 | 0.087* | |
C10 | 0.5414 (6) | 0.5194 (5) | 0.4778 (3) | 0.0473 (17) | |
C11 | 0.5956 (8) | 0.5812 (6) | 0.4941 (4) | 0.064 (2) | |
H11 | 0.5836 | 0.5987 | 0.5361 | 0.077* | |
C12 | 0.6671 (7) | 0.6179 (6) | 0.4498 (4) | 0.062 (2) | |
H12 | 0.7008 | 0.6604 | 0.4627 | 0.074* | |
C13 | 1.0142 (7) | 0.4618 (4) | 0.1806 (3) | 0.0445 (16) | |
C14 | 0.9186 (8) | 0.4251 (5) | 0.2047 (4) | 0.061 (2) | |
H14 | 0.8407 | 0.4606 | 0.2153 | 0.073* | |
C15 | 0.9390 (12) | 0.3367 (7) | 0.2129 (5) | 0.086 (3) | |
H15 | 0.8738 | 0.3131 | 0.2282 | 0.103* | |
C16 | 1.0505 (14) | 0.2838 (6) | 0.1992 (5) | 0.093 (3) | |
H16 | 1.0623 | 0.2241 | 0.2056 | 0.112* | |
C17 | 1.1473 (11) | 0.3168 (6) | 0.1760 (5) | 0.092 (3) | |
H17 | 1.2249 | 0.2797 | 0.1669 | 0.110* | |
C18 | 1.1293 (8) | 0.4070 (5) | 0.1658 (4) | 0.063 (2) | |
H18 | 1.1943 | 0.4299 | 0.1491 | 0.076* | |
C19 | 1.0747 (6) | 0.6024 (4) | 0.0971 (3) | 0.0398 (15) | |
C20 | 1.1738 (7) | 0.6396 (5) | 0.0979 (4) | 0.0550 (19) | |
H20 | 1.2033 | 0.6488 | 0.1382 | 0.066* | |
C21 | 1.2309 (9) | 0.6638 (5) | 0.0393 (4) | 0.071 (2) | |
H21 | 1.2968 | 0.6896 | 0.0407 | 0.085* | |
C22 | 1.1886 (9) | 0.6493 (5) | −0.0210 (4) | 0.067 (2) | |
H22 | 1.2259 | 0.6651 | −0.0602 | 0.081* | |
C23 | 1.0928 (9) | 0.6119 (6) | −0.0220 (4) | 0.068 (2) | |
H23 | 1.0648 | 0.6016 | −0.0624 | 0.081* | |
C24 | 1.0350 (7) | 0.5885 (5) | 0.0361 (3) | 0.0534 (18) | |
H24 | 0.9688 | 0.5632 | 0.0340 | 0.064* | |
C25 | 1.0569 (7) | 0.4842 (4) | 0.3587 (3) | 0.0458 (16) | |
C26 | 0.9971 (8) | 0.4582 (6) | 0.4146 (4) | 0.068 (2) | |
H26 | 0.9282 | 0.4977 | 0.4305 | 0.081* | |
C27 | 1.0364 (10) | 0.3756 (6) | 0.4474 (4) | 0.082 (3) | |
H27 | 0.9945 | 0.3594 | 0.4849 | 0.099* | |
C28 | 1.1388 (11) | 0.3170 (6) | 0.4240 (5) | 0.084 (3) | |
H28 | 1.1665 | 0.2610 | 0.4460 | 0.100* | |
C29 | 1.1986 (10) | 0.3405 (6) | 0.3695 (5) | 0.089 (3) | |
H29 | 1.2669 | 0.3005 | 0.3538 | 0.107* | |
C30 | 1.1588 (8) | 0.4248 (5) | 0.3364 (4) | 0.067 (2) | |
H30 | 1.2015 | 0.4406 | 0.2991 | 0.081* | |
C31 | 1.0784 (7) | 0.6594 (4) | 0.3634 (3) | 0.0447 (16) | |
C32 | 1.0151 (10) | 0.7392 (6) | 0.3748 (6) | 0.098 (4) | |
H32 | 0.9295 | 0.7595 | 0.3636 | 0.117* | |
C33 | 1.0740 (12) | 0.7925 (7) | 0.4027 (7) | 0.121 (5) | |
H33 | 1.0285 | 0.8486 | 0.4087 | 0.145* | |
C34 | 1.1969 (11) | 0.7635 (7) | 0.4213 (5) | 0.094 (3) | |
H34 | 1.2365 | 0.7982 | 0.4413 | 0.113* | |
C35 | 1.2608 (11) | 0.6829 (8) | 0.4102 (7) | 0.131 (5) | |
H35 | 1.3458 | 0.6619 | 0.4225 | 0.157* | |
C36 | 1.2027 (9) | 0.6315 (6) | 0.3812 (6) | 0.097 (4) | |
H36 | 1.2493 | 0.5763 | 0.3736 | 0.117* | |
C37 | 0.5734 (6) | 0.8662 (4) | 0.1014 (3) | 0.0441 (16) | |
C38 | 0.4900 (7) | 0.8261 (5) | 0.0793 (4) | 0.0571 (19) | |
H38 | 0.5128 | 0.7659 | 0.0819 | 0.069* | |
C39 | 0.3730 (8) | 0.8729 (6) | 0.0533 (5) | 0.073 (2) | |
H39 | 0.3181 | 0.8444 | 0.0382 | 0.088* | |
C40 | 0.3380 (8) | 0.9606 (6) | 0.0498 (5) | 0.073 (2) | |
H40 | 0.2591 | 0.9922 | 0.0323 | 0.087* | |
C41 | 0.4191 (8) | 1.0023 (5) | 0.0721 (4) | 0.071 (2) | |
H41 | 0.3946 | 1.0624 | 0.0702 | 0.086* | |
C42 | 0.5378 (7) | 0.9556 (5) | 0.0976 (4) | 0.059 (2) | |
H42 | 0.5931 | 0.9844 | 0.1121 | 0.071* | |
C43 | 0.8411 (6) | 0.8383 (4) | 0.0809 (3) | 0.0398 (15) | |
C44 | 0.9262 (7) | 0.8800 (5) | 0.1004 (4) | 0.0577 (19) | |
H44 | 0.9246 | 0.8949 | 0.1431 | 0.069* | |
C45 | 1.0150 (8) | 0.8998 (6) | 0.0553 (5) | 0.079 (3) | |
H45 | 1.0732 | 0.9269 | 0.0688 | 0.094* | |
C46 | 1.0176 (8) | 0.8800 (6) | −0.0076 (5) | 0.072 (3) | |
H46 | 1.0762 | 0.8945 | −0.0372 | 0.086* | |
C47 | 0.9345 (9) | 0.8392 (5) | −0.0273 (4) | 0.070 (2) | |
H47 | 0.9370 | 0.8250 | −0.0703 | 0.084* | |
C48 | 0.8463 (7) | 0.8185 (5) | 0.0161 (4) | 0.0553 (19) | |
H48 | 0.7894 | 0.7909 | 0.0017 | 0.066* | |
C49 | 0.5100 (6) | 0.8011 (5) | 0.2594 (3) | 0.0461 (16) | |
C50 | 0.4726 (8) | 0.7277 (5) | 0.2510 (4) | 0.065 (2) | |
H50 | 0.5312 | 0.6736 | 0.2573 | 0.078* | |
C51 | 0.3485 (9) | 0.7345 (7) | 0.2334 (5) | 0.091 (3) | |
H51 | 0.3243 | 0.6846 | 0.2288 | 0.109* | |
C52 | 0.2625 (9) | 0.8124 (8) | 0.2227 (5) | 0.093 (3) | |
H52 | 0.1804 | 0.8161 | 0.2096 | 0.112* | |
C53 | 0.2958 (8) | 0.8862 (7) | 0.2313 (5) | 0.085 (3) | |
H53 | 0.2357 | 0.9397 | 0.2249 | 0.102* | |
C54 | 0.4209 (7) | 0.8813 (5) | 0.2496 (4) | 0.063 (2) | |
H54 | 0.4436 | 0.9314 | 0.2552 | 0.076* | |
C55 | 0.6621 (7) | 0.8577 (5) | 0.3482 (3) | 0.0506 (17) | |
C56 | 0.5872 (9) | 0.8459 (6) | 0.4022 (4) | 0.082 (3) | |
H56 | 0.5355 | 0.8089 | 0.4023 | 0.098* | |
C57 | 0.5906 (13) | 0.8909 (9) | 0.4570 (5) | 0.118 (4) | |
H57 | 0.5426 | 0.8820 | 0.4940 | 0.142* | |
C58 | 0.6634 (15) | 0.9473 (9) | 0.4567 (6) | 0.117 (4) | |
H58 | 0.6628 | 0.9774 | 0.4929 | 0.141* | |
C59 | 0.7358 (11) | 0.9597 (8) | 0.4046 (6) | 0.100 (3) | |
H59 | 0.7848 | 0.9985 | 0.4045 | 0.120* | |
C60 | 0.7373 (8) | 0.9144 (6) | 0.3511 (4) | 0.070 (2) | |
H60 | 0.7900 | 0.9220 | 0.3159 | 0.084* | |
B1 | 0.9148 (14) | 0.0567 (12) | 0.2166 (8) | 0.103 (5) | |
B2 | 0.4736 (11) | 0.4350 (9) | 0.2520 (6) | 0.081 (3) | |
F1 | 0.9614 (9) | −0.0327 (6) | 0.2453 (5) | 0.168 (3) | |
F2 | 1.0190 (10) | 0.0665 (7) | 0.1914 (5) | 0.187 (4) | |
F3 | 0.8700 (9) | 0.1076 (7) | 0.2601 (5) | 0.186 (4) | |
F4 | 0.8255 (10) | 0.0519 (7) | 0.1752 (5) | 0.196 (4) | |
F5 | 0.5923 (7) | 0.4249 (6) | 0.2422 (4) | 0.146 (3) | |
F6 | 0.4082 (9) | 0.5169 (6) | 0.2445 (5) | 0.177 (3) | |
F7 | 0.4209 (9) | 0.4062 (6) | 0.2021 (4) | 0.167 (3) | |
F8 | 0.4520 (7) | 0.3947 (5) | 0.3116 (3) | 0.133 (2) | |
C61 | 0.8862 (11) | 0.9237 (16) | 0.6448 (6) | 0.123 (8) | 0.25 |
H61A | 0.9490 | 0.8679 | 0.6511 | 0.148* | 0.25 |
H61B | 0.8997 | 0.9561 | 0.6798 | 0.148* | 0.25 |
Cl1 | 0.9139 (14) | 0.9790 (8) | 0.5688 (5) | 0.088 (4) | 0.25 |
Cl2 | 0.7380 (10) | 0.9060 (8) | 0.6547 (9) | 0.085 (4) | 0.25 |
C61' | 0.8862 (11) | 0.9237 (16) | 0.6448 (6) | 0.123 (8) | 0.25 |
H61C | 0.9049 | 0.9650 | 0.6711 | 0.148* | 0.25 |
H61D | 0.9262 | 0.8660 | 0.6667 | 0.148* | 0.25 |
Cl1' | 0.9515 (13) | 0.9359 (9) | 0.5672 (5) | 0.088 (4) | 0.25 |
Cl2' | 0.7237 (10) | 0.9386 (11) | 0.6427 (8) | 0.093 (5) | 0.25 |
C62 | 0.2991 (13) | 0.7668 (9) | 0.6418 (7) | 0.129 (4) | |
H62A | 0.2551 | 0.8206 | 0.6583 | 0.155* | |
H62B | 0.3513 | 0.7293 | 0.6776 | 0.155* | |
Cl3 | 0.3935 (6) | 0.7879 (4) | 0.5765 (3) | 0.198 (2) | |
Cl4 | 0.1885 (5) | 0.7164 (4) | 0.6152 (2) | 0.1833 (19) | |
C63 | 0.4294 (14) | 0.8051 (9) | 0.8138 (7) | 0.135 (5) | |
H63A | 0.4437 | 0.7503 | 0.7961 | 0.162* | |
H63B | 0.3401 | 0.8352 | 0.8086 | 0.162* | |
Cl5 | 0.5165 (7) | 0.8663 (4) | 0.7710 (3) | 0.227 (3) | |
Cl6 | 0.4723 (6) | 0.7864 (3) | 0.8974 (2) | 0.192 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0361 (4) | 0.0390 (4) | 0.0439 (5) | −0.0160 (3) | −0.0046 (3) | −0.0070 (3) |
Cu2 | 0.0386 (5) | 0.0483 (5) | 0.0426 (5) | −0.0170 (4) | 0.0059 (3) | 0.0012 (4) |
P1 | 0.0330 (8) | 0.0404 (9) | 0.0350 (9) | −0.0125 (7) | −0.0017 (6) | −0.0068 (7) |
P2 | 0.0376 (9) | 0.0466 (10) | 0.0329 (9) | −0.0138 (8) | 0.0007 (7) | −0.0011 (7) |
P3 | 0.0380 (9) | 0.0384 (9) | 0.0364 (9) | −0.0165 (7) | −0.0018 (7) | −0.0025 (7) |
P4 | 0.0374 (9) | 0.0428 (9) | 0.0404 (9) | −0.0148 (7) | 0.0052 (7) | −0.0047 (7) |
N1 | 0.048 (3) | 0.045 (3) | 0.060 (4) | −0.016 (3) | −0.012 (3) | −0.011 (3) |
N2 | 0.048 (3) | 0.059 (4) | 0.054 (4) | −0.025 (3) | 0.007 (3) | 0.006 (3) |
C1 | 0.035 (3) | 0.048 (4) | 0.031 (3) | −0.015 (3) | −0.001 (3) | −0.006 (3) |
C2 | 0.049 (4) | 0.045 (4) | 0.040 (4) | −0.024 (3) | 0.005 (3) | −0.008 (3) |
C3 | 0.054 (4) | 0.053 (4) | 0.063 (5) | −0.024 (4) | −0.011 (4) | −0.004 (4) |
C4 | 0.057 (5) | 0.057 (4) | 0.052 (4) | −0.025 (4) | −0.011 (3) | −0.008 (3) |
C5 | 0.032 (3) | 0.046 (4) | 0.052 (4) | −0.013 (3) | −0.006 (3) | −0.009 (3) |
C6 | 0.101 (7) | 0.136 (9) | 0.054 (5) | −0.096 (7) | 0.003 (5) | −0.018 (5) |
C7 | 0.100 (7) | 0.108 (7) | 0.046 (5) | −0.074 (6) | −0.005 (4) | −0.017 (4) |
C8 | 0.093 (7) | 0.074 (6) | 0.054 (5) | −0.041 (5) | 0.028 (4) | −0.009 (4) |
C9 | 0.097 (7) | 0.069 (5) | 0.066 (5) | −0.048 (5) | 0.032 (5) | −0.013 (4) |
C10 | 0.047 (4) | 0.054 (4) | 0.039 (4) | −0.017 (3) | 0.006 (3) | 0.006 (3) |
C11 | 0.068 (5) | 0.092 (6) | 0.043 (4) | −0.045 (5) | 0.005 (4) | 0.001 (4) |
C12 | 0.062 (5) | 0.084 (6) | 0.053 (5) | −0.043 (4) | 0.003 (4) | −0.001 (4) |
C13 | 0.052 (4) | 0.042 (4) | 0.040 (4) | −0.016 (3) | −0.006 (3) | −0.001 (3) |
C14 | 0.074 (5) | 0.059 (5) | 0.056 (5) | −0.031 (4) | 0.007 (4) | 0.000 (4) |
C15 | 0.129 (10) | 0.069 (6) | 0.075 (6) | −0.058 (7) | 0.003 (6) | 0.002 (5) |
C16 | 0.157 (12) | 0.048 (6) | 0.077 (7) | −0.036 (7) | −0.003 (7) | 0.001 (5) |
C17 | 0.113 (9) | 0.057 (6) | 0.091 (7) | 0.008 (6) | −0.009 (6) | −0.022 (5) |
C18 | 0.061 (5) | 0.051 (5) | 0.073 (5) | −0.007 (4) | −0.005 (4) | −0.004 (4) |
C19 | 0.044 (4) | 0.036 (3) | 0.036 (4) | −0.006 (3) | 0.005 (3) | −0.004 (3) |
C20 | 0.070 (5) | 0.065 (5) | 0.044 (4) | −0.039 (4) | 0.011 (4) | −0.017 (3) |
C21 | 0.083 (6) | 0.070 (6) | 0.073 (6) | −0.042 (5) | 0.027 (5) | −0.014 (4) |
C22 | 0.084 (6) | 0.054 (5) | 0.054 (5) | −0.007 (4) | 0.021 (4) | 0.002 (4) |
C23 | 0.080 (6) | 0.083 (6) | 0.036 (4) | −0.011 (5) | 0.003 (4) | −0.014 (4) |
C24 | 0.050 (4) | 0.071 (5) | 0.039 (4) | −0.015 (4) | −0.001 (3) | −0.011 (3) |
C25 | 0.049 (4) | 0.052 (4) | 0.038 (4) | −0.018 (3) | −0.005 (3) | −0.001 (3) |
C26 | 0.073 (6) | 0.068 (5) | 0.055 (5) | −0.017 (4) | 0.006 (4) | 0.010 (4) |
C27 | 0.102 (8) | 0.081 (7) | 0.065 (6) | −0.039 (6) | 0.002 (5) | 0.023 (5) |
C28 | 0.116 (9) | 0.051 (5) | 0.079 (7) | −0.022 (6) | −0.020 (6) | 0.010 (5) |
C29 | 0.103 (8) | 0.055 (5) | 0.086 (7) | 0.014 (5) | 0.002 (6) | −0.003 (5) |
C30 | 0.068 (5) | 0.061 (5) | 0.061 (5) | −0.002 (4) | 0.004 (4) | 0.004 (4) |
C31 | 0.052 (4) | 0.051 (4) | 0.032 (3) | −0.017 (3) | −0.005 (3) | −0.003 (3) |
C32 | 0.073 (6) | 0.080 (7) | 0.147 (10) | −0.014 (5) | −0.036 (6) | −0.051 (7) |
C33 | 0.106 (9) | 0.086 (8) | 0.176 (13) | −0.013 (7) | −0.042 (9) | −0.064 (8) |
C34 | 0.104 (8) | 0.081 (7) | 0.104 (8) | −0.029 (6) | −0.043 (6) | −0.020 (6) |
C35 | 0.091 (8) | 0.089 (8) | 0.212 (15) | −0.014 (7) | −0.085 (9) | −0.030 (9) |
C36 | 0.075 (7) | 0.071 (6) | 0.149 (10) | −0.015 (5) | −0.050 (6) | −0.027 (6) |
C37 | 0.043 (4) | 0.047 (4) | 0.042 (4) | −0.014 (3) | 0.001 (3) | −0.002 (3) |
C38 | 0.045 (4) | 0.053 (4) | 0.073 (5) | −0.011 (4) | −0.011 (4) | −0.010 (4) |
C39 | 0.049 (5) | 0.069 (6) | 0.101 (7) | −0.017 (4) | −0.019 (5) | −0.007 (5) |
C40 | 0.044 (5) | 0.067 (6) | 0.097 (7) | −0.008 (4) | −0.008 (4) | 0.013 (5) |
C41 | 0.063 (5) | 0.050 (5) | 0.092 (6) | −0.007 (4) | −0.004 (5) | 0.009 (4) |
C42 | 0.060 (5) | 0.044 (4) | 0.072 (5) | −0.017 (4) | −0.015 (4) | 0.009 (4) |
C43 | 0.042 (4) | 0.029 (3) | 0.046 (4) | −0.008 (3) | 0.003 (3) | −0.001 (3) |
C44 | 0.053 (5) | 0.062 (5) | 0.063 (5) | −0.024 (4) | 0.008 (4) | −0.007 (4) |
C45 | 0.055 (5) | 0.086 (6) | 0.097 (7) | −0.035 (5) | 0.017 (5) | 0.009 (5) |
C46 | 0.061 (5) | 0.068 (6) | 0.078 (6) | −0.013 (4) | 0.031 (5) | 0.007 (5) |
C47 | 0.096 (7) | 0.059 (5) | 0.046 (5) | −0.008 (5) | 0.024 (4) | −0.003 (4) |
C48 | 0.064 (5) | 0.049 (4) | 0.052 (4) | −0.015 (4) | 0.005 (4) | −0.007 (3) |
C49 | 0.040 (4) | 0.053 (4) | 0.048 (4) | −0.020 (3) | 0.008 (3) | −0.003 (3) |
C50 | 0.059 (5) | 0.065 (5) | 0.074 (5) | −0.029 (4) | −0.005 (4) | 0.004 (4) |
C51 | 0.075 (7) | 0.097 (8) | 0.114 (8) | −0.056 (6) | −0.033 (6) | 0.017 (6) |
C52 | 0.056 (6) | 0.114 (9) | 0.117 (9) | −0.044 (6) | −0.017 (5) | 0.009 (7) |
C53 | 0.042 (5) | 0.101 (8) | 0.092 (7) | 0.007 (5) | 0.002 (4) | 0.005 (6) |
C54 | 0.048 (5) | 0.062 (5) | 0.079 (6) | −0.012 (4) | 0.011 (4) | −0.010 (4) |
C55 | 0.047 (4) | 0.054 (4) | 0.047 (4) | −0.004 (3) | 0.002 (3) | −0.012 (3) |
C56 | 0.091 (7) | 0.091 (7) | 0.062 (6) | −0.021 (6) | 0.023 (5) | −0.017 (5) |
C57 | 0.144 (12) | 0.155 (12) | 0.060 (7) | −0.037 (10) | 0.045 (7) | −0.043 (7) |
C58 | 0.151 (12) | 0.121 (10) | 0.081 (8) | −0.018 (9) | −0.011 (8) | −0.057 (8) |
C59 | 0.118 (9) | 0.114 (9) | 0.083 (8) | −0.039 (7) | 0.003 (7) | −0.051 (7) |
C60 | 0.077 (6) | 0.073 (6) | 0.070 (6) | −0.027 (5) | 0.003 (4) | −0.028 (5) |
B1 | 0.081 (9) | 0.138 (13) | 0.104 (10) | −0.031 (9) | 0.001 (8) | −0.061 (10) |
B2 | 0.068 (7) | 0.094 (9) | 0.083 (8) | −0.035 (7) | −0.008 (6) | 0.007 (7) |
F1 | 0.171 (7) | 0.155 (6) | 0.176 (7) | −0.053 (6) | −0.006 (5) | 0.007 (5) |
F2 | 0.179 (7) | 0.185 (7) | 0.199 (7) | −0.067 (6) | 0.055 (6) | −0.001 (6) |
F3 | 0.178 (7) | 0.203 (7) | 0.173 (6) | −0.010 (6) | 0.010 (5) | −0.111 (6) |
F4 | 0.171 (7) | 0.195 (7) | 0.207 (7) | 0.007 (6) | −0.057 (6) | −0.089 (6) |
F5 | 0.083 (4) | 0.202 (7) | 0.138 (5) | −0.036 (4) | 0.002 (4) | 0.028 (5) |
F6 | 0.183 (7) | 0.121 (5) | 0.192 (7) | 0.006 (5) | 0.040 (6) | 0.006 (5) |
F7 | 0.183 (7) | 0.202 (7) | 0.149 (6) | −0.106 (6) | −0.012 (5) | −0.025 (5) |
F8 | 0.116 (5) | 0.163 (6) | 0.115 (5) | −0.055 (4) | −0.003 (4) | 0.035 (4) |
C61 | 0.125 (10) | 0.131 (10) | 0.115 (10) | −0.033 (7) | −0.010 (7) | −0.020 (7) |
Cl1 | 0.110 (8) | 0.085 (7) | 0.088 (6) | −0.052 (6) | −0.004 (5) | −0.022 (5) |
Cl2 | 0.102 (7) | 0.055 (6) | 0.092 (8) | −0.015 (5) | 0.017 (6) | 0.001 (5) |
C61' | 0.125 (10) | 0.131 (10) | 0.115 (10) | −0.033 (7) | −0.010 (7) | −0.020 (7) |
Cl1' | 0.086 (7) | 0.102 (8) | 0.071 (6) | −0.016 (6) | 0.006 (5) | −0.017 (6) |
Cl2' | 0.098 (7) | 0.107 (9) | 0.065 (7) | −0.012 (6) | 0.011 (5) | −0.019 (7) |
C62 | 0.137 (8) | 0.130 (8) | 0.115 (8) | −0.018 (7) | 0.011 (7) | −0.031 (7) |
Cl3 | 0.212 (5) | 0.187 (4) | 0.187 (4) | −0.058 (4) | 0.041 (4) | 0.009 (3) |
Cl4 | 0.197 (5) | 0.200 (4) | 0.160 (4) | −0.059 (4) | 0.002 (3) | −0.035 (3) |
C63 | 0.138 (8) | 0.120 (8) | 0.145 (9) | −0.028 (7) | −0.013 (7) | −0.020 (7) |
Cl5 | 0.242 (6) | 0.204 (5) | 0.221 (5) | −0.055 (4) | 0.047 (4) | 0.005 (4) |
Cl6 | 0.242 (5) | 0.182 (4) | 0.141 (3) | −0.044 (4) | −0.033 (3) | −0.007 (3) |
Cu1—N1 | 2.018 (5) | C30—H30 | 0.9300 |
Cu1—P3 | 2.2329 (18) | C31—C32 | 1.334 (11) |
Cu1—P1 | 2.2515 (18) | C31—C36 | 1.356 (11) |
Cu2—N2 | 2.022 (5) | C32—C33 | 1.387 (12) |
Cu2—P2 | 2.2397 (19) | C32—H32 | 0.9300 |
Cu2—P4 | 2.2505 (19) | C33—C34 | 1.347 (14) |
P1—C13 | 1.812 (7) | C33—H33 | 0.9300 |
P1—C19 | 1.821 (6) | C34—C35 | 1.345 (15) |
P1—C1 | 1.834 (6) | C34—H34 | 0.9300 |
P2—C25 | 1.823 (7) | C35—C36 | 1.367 (13) |
P2—C1 | 1.833 (6) | C35—H35 | 0.9300 |
P2—C31 | 1.838 (7) | C36—H36 | 0.9300 |
P3—C43 | 1.820 (6) | C37—C38 | 1.368 (10) |
P3—C37 | 1.821 (7) | C37—C42 | 1.382 (10) |
P3—C2 | 1.841 (6) | C38—C39 | 1.378 (10) |
P4—C55 | 1.808 (7) | C38—H38 | 0.9300 |
P4—C49 | 1.815 (7) | C39—C40 | 1.355 (11) |
P4—C2 | 1.835 (6) | C39—H39 | 0.9300 |
N1—C3 | 1.327 (9) | C40—C41 | 1.368 (12) |
N1—C7 | 1.328 (9) | C40—H40 | 0.9300 |
N2—C8 | 1.312 (10) | C41—C42 | 1.388 (11) |
N2—C12 | 1.336 (9) | C41—H41 | 0.9300 |
C1—H1A | 0.9700 | C42—H42 | 0.9300 |
C1—H1B | 0.9700 | C43—C44 | 1.381 (9) |
C2—H2A | 0.9700 | C43—C48 | 1.392 (9) |
C2—H2B | 0.9700 | C44—C45 | 1.399 (10) |
C3—C4 | 1.377 (9) | C44—H44 | 0.9300 |
C3—H3 | 0.9300 | C45—C46 | 1.356 (12) |
C4—C5 | 1.357 (9) | C45—H45 | 0.9300 |
C4—H4 | 0.9300 | C46—C47 | 1.353 (12) |
C5—C6 | 1.376 (10) | C46—H46 | 0.9300 |
C5—C5i | 1.499 (12) | C47—C48 | 1.379 (11) |
C6—C7 | 1.366 (10) | C47—H47 | 0.9300 |
C6—H6 | 0.9300 | C48—H48 | 0.9300 |
C7—H7 | 0.9300 | C49—C50 | 1.385 (10) |
C8—C9 | 1.385 (10) | C49—C54 | 1.389 (10) |
C8—H8 | 0.9300 | C50—C51 | 1.388 (11) |
C9—C10 | 1.373 (10) | C50—H50 | 0.9300 |
C9—H9 | 0.9300 | C51—C52 | 1.347 (14) |
C10—C11 | 1.368 (10) | C51—H51 | 0.9300 |
C10—C10ii | 1.477 (12) | C52—C53 | 1.369 (14) |
C11—C12 | 1.370 (10) | C52—H52 | 0.9300 |
C11—H11 | 0.9300 | C53—C54 | 1.408 (11) |
C12—H12 | 0.9300 | C53—H53 | 0.9300 |
C13—C18 | 1.385 (10) | C54—H54 | 0.9300 |
C13—C14 | 1.394 (9) | C55—C56 | 1.386 (11) |
C14—C15 | 1.374 (12) | C55—C60 | 1.398 (11) |
C14—H14 | 0.9300 | C56—C57 | 1.411 (14) |
C15—C16 | 1.337 (15) | C56—H56 | 0.9300 |
C15—H15 | 0.9300 | C57—C58 | 1.365 (17) |
C16—C17 | 1.366 (15) | C57—H57 | 0.9300 |
C16—H16 | 0.9300 | C58—C59 | 1.342 (16) |
C17—C18 | 1.406 (12) | C58—H58 | 0.9300 |
C17—H17 | 0.9300 | C59—C60 | 1.383 (12) |
C18—H18 | 0.9300 | C59—H59 | 0.9300 |
C19—C20 | 1.380 (9) | C60—H60 | 0.9300 |
C19—C24 | 1.387 (9) | B1—F3 | 1.283 (15) |
C20—C21 | 1.399 (10) | B1—F2 | 1.288 (15) |
C20—H20 | 0.9300 | B1—F4 | 1.329 (15) |
C21—C22 | 1.386 (12) | B1—F1 | 1.444 (18) |
C21—H21 | 0.9300 | B2—F5 | 1.285 (12) |
C22—C23 | 1.351 (12) | B2—F6 | 1.314 (14) |
C22—H22 | 0.9300 | B2—F8 | 1.352 (12) |
C23—C24 | 1.392 (10) | B2—F7 | 1.366 (13) |
C23—H23 | 0.9300 | C61—Cl2 | 1.732 (10) |
C24—H24 | 0.9300 | C61—Cl1 | 1.751 (10) |
C25—C30 | 1.375 (10) | C61—H61A | 0.9700 |
C25—C26 | 1.382 (10) | C61—H61B | 0.9700 |
C26—C27 | 1.373 (12) | C62—Cl3 | 1.728 (14) |
C26—H26 | 0.9300 | C62—Cl4 | 1.762 (14) |
C27—C28 | 1.380 (14) | C62—H62A | 0.9700 |
C27—H27 | 0.9300 | C62—H62B | 0.9700 |
C28—C29 | 1.346 (13) | C63—Cl5 | 1.708 (15) |
C28—H28 | 0.9300 | C63—Cl6 | 1.738 (14) |
C29—C30 | 1.398 (11) | C63—H63A | 0.9700 |
C29—H29 | 0.9300 | C63—H63B | 0.9700 |
N1—Cu1—P3 | 118.66 (17) | C28—C29—C30 | 120.5 (9) |
N1—Cu1—P1 | 115.59 (17) | C28—C29—H29 | 119.7 |
P3—Cu1—P1 | 122.10 (7) | C30—C29—H29 | 119.7 |
N2—Cu2—P2 | 116.50 (18) | C25—C30—C29 | 120.2 (8) |
N2—Cu2—P4 | 111.90 (18) | C25—C30—H30 | 119.9 |
P2—Cu2—P4 | 129.66 (7) | C29—C30—H30 | 119.9 |
C13—P1—C19 | 105.0 (3) | C32—C31—C36 | 117.6 (8) |
C13—P1—C1 | 105.3 (3) | C32—C31—P2 | 119.0 (6) |
C19—P1—C1 | 103.3 (3) | C36—C31—P2 | 123.4 (6) |
C13—P1—Cu1 | 117.8 (2) | C31—C32—C33 | 121.5 (9) |
C19—P1—Cu1 | 102.7 (2) | C31—C32—H32 | 119.2 |
C1—P1—Cu1 | 120.6 (2) | C33—C32—H32 | 119.2 |
C25—P2—C1 | 107.6 (3) | C34—C33—C32 | 120.4 (10) |
C25—P2—C31 | 105.6 (3) | C34—C33—H33 | 119.8 |
C1—P2—C31 | 100.5 (3) | C32—C33—H33 | 119.8 |
C25—P2—Cu2 | 117.0 (2) | C35—C34—C33 | 118.2 (9) |
C1—P2—Cu2 | 115.5 (2) | C35—C34—H34 | 120.9 |
C31—P2—Cu2 | 108.9 (2) | C33—C34—H34 | 120.9 |
C43—P3—C37 | 104.6 (3) | C34—C35—C36 | 121.0 (10) |
C43—P3—C2 | 105.2 (3) | C34—C35—H35 | 119.5 |
C37—P3—C2 | 103.8 (3) | C36—C35—H35 | 119.5 |
C43—P3—Cu1 | 104.3 (2) | C31—C36—C35 | 121.3 (9) |
C37—P3—Cu1 | 120.8 (2) | C31—C36—H36 | 119.4 |
C2—P3—Cu1 | 116.5 (2) | C35—C36—H36 | 119.4 |
C55—P4—C49 | 104.8 (3) | C38—C37—C42 | 118.6 (7) |
C55—P4—C2 | 103.5 (3) | C38—C37—P3 | 120.4 (5) |
C49—P4—C2 | 106.3 (3) | C42—C37—P3 | 121.0 (5) |
C55—P4—Cu2 | 107.5 (2) | C37—C38—C39 | 121.3 (7) |
C49—P4—Cu2 | 116.4 (2) | C37—C38—H38 | 119.4 |
C2—P4—Cu2 | 117.0 (2) | C39—C38—H38 | 119.4 |
C3—N1—C7 | 115.7 (6) | C40—C39—C38 | 120.1 (8) |
C3—N1—Cu1 | 124.9 (5) | C40—C39—H39 | 120.0 |
C7—N1—Cu1 | 119.5 (5) | C38—C39—H39 | 120.0 |
C8—N2—C12 | 116.0 (6) | C39—C40—C41 | 119.8 (8) |
C8—N2—Cu2 | 121.9 (5) | C39—C40—H40 | 120.1 |
C12—N2—Cu2 | 122.0 (5) | C41—C40—H40 | 120.1 |
P2—C1—P1 | 116.7 (3) | C40—C41—C42 | 120.5 (8) |
P2—C1—H1A | 108.1 | C40—C41—H41 | 119.8 |
P1—C1—H1A | 108.1 | C42—C41—H41 | 119.8 |
P2—C1—H1B | 108.1 | C37—C42—C41 | 119.7 (7) |
P1—C1—H1B | 108.1 | C37—C42—H42 | 120.1 |
H1A—C1—H1B | 107.3 | C41—C42—H42 | 120.1 |
P4—C2—P3 | 111.3 (3) | C44—C43—C48 | 117.9 (6) |
P4—C2—H2A | 109.4 | C44—C43—P3 | 124.3 (5) |
P3—C2—H2A | 109.4 | C48—C43—P3 | 117.7 (5) |
P4—C2—H2B | 109.4 | C43—C44—C45 | 119.6 (8) |
P3—C2—H2B | 109.4 | C43—C44—H44 | 120.2 |
H2A—C2—H2B | 108.0 | C45—C44—H44 | 120.2 |
N1—C3—C4 | 123.4 (7) | C46—C45—C44 | 121.1 (8) |
N1—C3—H3 | 118.3 | C46—C45—H45 | 119.4 |
C4—C3—H3 | 118.3 | C44—C45—H45 | 119.4 |
C5—C4—C3 | 120.9 (7) | C47—C46—C45 | 119.8 (8) |
C5—C4—H4 | 119.6 | C47—C46—H46 | 120.1 |
C3—C4—H4 | 119.6 | C45—C46—H46 | 120.1 |
C4—C5—C6 | 115.9 (6) | C46—C47—C48 | 120.5 (8) |
C4—C5—C5i | 123.0 (8) | C46—C47—H47 | 119.8 |
C6—C5—C5i | 121.1 (8) | C48—C47—H47 | 119.8 |
C7—C6—C5 | 120.4 (7) | C47—C48—C43 | 121.1 (8) |
C7—C6—H6 | 119.8 | C47—C48—H48 | 119.5 |
C5—C6—H6 | 119.8 | C43—C48—H48 | 119.5 |
N1—C7—C6 | 123.8 (7) | C50—C49—C54 | 118.6 (7) |
N1—C7—H7 | 118.1 | C50—C49—P4 | 119.4 (6) |
C6—C7—H7 | 118.1 | C54—C49—P4 | 122.0 (6) |
N2—C8—C9 | 123.9 (8) | C49—C50—C51 | 120.5 (9) |
N2—C8—H8 | 118.1 | C49—C50—H50 | 119.8 |
C9—C8—H8 | 118.1 | C51—C50—H50 | 119.8 |
C10—C9—C8 | 120.3 (8) | C52—C51—C50 | 120.9 (9) |
C10—C9—H9 | 119.8 | C52—C51—H51 | 119.5 |
C8—C9—H9 | 119.8 | C50—C51—H51 | 119.5 |
C11—C10—C9 | 115.3 (6) | C51—C52—C53 | 120.1 (9) |
C11—C10—C10ii | 123.8 (8) | C51—C52—H52 | 119.9 |
C9—C10—C10ii | 120.9 (8) | C53—C52—H52 | 119.9 |
C10—C11—C12 | 121.4 (7) | C52—C53—C54 | 120.2 (9) |
C10—C11—H11 | 119.3 | C52—C53—H53 | 119.9 |
C12—C11—H11 | 119.3 | C54—C53—H53 | 119.9 |
N2—C12—C11 | 123.0 (7) | C49—C54—C53 | 119.6 (8) |
N2—C12—H12 | 118.5 | C49—C54—H54 | 120.2 |
C11—C12—H12 | 118.5 | C53—C54—H54 | 120.2 |
C18—C13—C14 | 118.4 (7) | C56—C55—C60 | 117.6 (8) |
C18—C13—P1 | 122.4 (6) | C56—C55—P4 | 118.8 (6) |
C14—C13—P1 | 119.2 (6) | C60—C55—P4 | 123.1 (6) |
C15—C14—C13 | 120.2 (9) | C55—C56—C57 | 119.0 (10) |
C15—C14—H14 | 119.9 | C55—C56—H56 | 120.5 |
C13—C14—H14 | 119.9 | C57—C56—H56 | 120.5 |
C16—C15—C14 | 121.3 (9) | C58—C57—C56 | 121.0 (10) |
C16—C15—H15 | 119.3 | C58—C57—H57 | 119.5 |
C14—C15—H15 | 119.3 | C56—C57—H57 | 119.5 |
C15—C16—C17 | 120.5 (9) | C59—C58—C57 | 120.5 (11) |
C15—C16—H16 | 119.7 | C59—C58—H58 | 119.7 |
C17—C16—H16 | 119.7 | C57—C58—H58 | 119.7 |
C16—C17—C18 | 119.8 (10) | C58—C59—C60 | 119.7 (11) |
C16—C17—H17 | 120.1 | C58—C59—H59 | 120.2 |
C18—C17—H17 | 120.1 | C60—C59—H59 | 120.2 |
C13—C18—C17 | 119.7 (9) | C59—C60—C55 | 122.1 (9) |
C13—C18—H18 | 120.1 | C59—C60—H60 | 119.0 |
C17—C18—H18 | 120.1 | C55—C60—H60 | 119.0 |
C20—C19—C24 | 117.5 (6) | F3—B1—F2 | 113.8 (13) |
C20—C19—P1 | 124.9 (5) | F3—B1—F4 | 112.0 (13) |
C24—C19—P1 | 117.4 (5) | F2—B1—F4 | 117.5 (14) |
C19—C20—C21 | 121.5 (7) | F3—B1—F1 | 112.6 (14) |
C19—C20—H20 | 119.3 | F2—B1—F1 | 98.0 (12) |
C21—C20—H20 | 119.3 | F4—B1—F1 | 101.4 (12) |
C22—C21—C20 | 119.6 (8) | F5—B2—F6 | 112.8 (11) |
C22—C21—H21 | 120.2 | F5—B2—F8 | 111.8 (10) |
C20—C21—H21 | 120.2 | F6—B2—F8 | 111.0 (11) |
C23—C22—C21 | 119.3 (7) | F5—B2—F7 | 110.1 (11) |
C23—C22—H22 | 120.3 | F6—B2—F7 | 99.9 (10) |
C21—C22—H22 | 120.3 | F8—B2—F7 | 110.7 (10) |
C22—C23—C24 | 121.2 (8) | Cl2—C61—Cl1 | 116.6 (10) |
C22—C23—H23 | 119.4 | Cl2—C61—H61A | 108.1 |
C24—C23—H23 | 119.4 | Cl1—C61—H61A | 108.1 |
C19—C24—C23 | 120.9 (7) | Cl2—C61—H61B | 108.1 |
C19—C24—H24 | 119.5 | Cl1—C61—H61B | 108.1 |
C23—C24—H24 | 119.5 | H61A—C61—H61B | 107.3 |
C30—C25—C26 | 118.0 (7) | Cl3—C62—Cl4 | 109.8 (7) |
C30—C25—P2 | 124.2 (5) | Cl3—C62—H62A | 109.7 |
C26—C25—P2 | 117.8 (6) | Cl4—C62—H62A | 109.7 |
C27—C26—C25 | 121.9 (9) | Cl3—C62—H62B | 109.7 |
C27—C26—H26 | 119.1 | Cl4—C62—H62B | 109.7 |
C25—C26—H26 | 119.1 | H62A—C62—H62B | 108.2 |
C26—C27—C28 | 119.1 (8) | Cl5—C63—Cl6 | 110.0 (8) |
C26—C27—H27 | 120.5 | Cl5—C63—H63A | 109.7 |
C28—C27—H27 | 120.5 | Cl6—C63—H63A | 109.7 |
C29—C28—C27 | 120.3 (8) | Cl5—C63—H63B | 109.7 |
C29—C28—H28 | 119.9 | Cl6—C63—H63B | 109.7 |
C27—C28—H28 | 119.9 | H63A—C63—H63B | 108.2 |
N1—Cu1—P1—C13 | −29.2 (3) | C21—C22—C23—C24 | 0.6 (13) |
P3—Cu1—P1—C13 | 172.7 (2) | C20—C19—C24—C23 | −0.4 (11) |
N1—Cu1—P1—C19 | 85.5 (3) | P1—C19—C24—C23 | 174.5 (6) |
P3—Cu1—P1—C19 | −72.6 (2) | C22—C23—C24—C19 | −0.4 (12) |
N1—Cu1—P1—C1 | −160.3 (3) | C1—P2—C25—C30 | 14.4 (7) |
P3—Cu1—P1—C1 | 41.5 (2) | C31—P2—C25—C30 | −92.2 (7) |
N2—Cu2—P2—C25 | 16.8 (3) | Cu2—P2—C25—C30 | 146.4 (6) |
P4—Cu2—P2—C25 | 179.5 (2) | C1—P2—C25—C26 | −166.7 (6) |
N2—Cu2—P2—C1 | 145.1 (3) | C31—P2—C25—C26 | 86.7 (6) |
P4—Cu2—P2—C1 | −52.2 (3) | Cu2—P2—C25—C26 | −34.7 (7) |
N2—Cu2—P2—C31 | −102.8 (3) | C30—C25—C26—C27 | −0.3 (12) |
P4—Cu2—P2—C31 | 59.9 (2) | P2—C25—C26—C27 | −179.3 (7) |
N1—Cu1—P3—C43 | −102.8 (3) | C25—C26—C27—C28 | 0.2 (14) |
P1—Cu1—P3—C43 | 54.7 (2) | C26—C27—C28—C29 | −0.4 (16) |
N1—Cu1—P3—C37 | 14.2 (3) | C27—C28—C29—C30 | 0.7 (16) |
P1—Cu1—P3—C37 | 171.8 (2) | C26—C25—C30—C29 | 0.6 (13) |
N1—Cu1—P3—C2 | 141.7 (3) | P2—C25—C30—C29 | 179.5 (7) |
P1—Cu1—P3—C2 | −60.8 (2) | C28—C29—C30—C25 | −0.9 (15) |
N2—Cu2—P4—C55 | 72.7 (3) | C25—P2—C31—C32 | −143.4 (8) |
P2—Cu2—P4—C55 | −90.6 (3) | C1—P2—C31—C32 | 104.9 (8) |
N2—Cu2—P4—C49 | −44.3 (3) | Cu2—P2—C31—C32 | −16.9 (8) |
P2—Cu2—P4—C49 | 152.4 (3) | C25—P2—C31—C36 | 40.8 (8) |
N2—Cu2—P4—C2 | −171.5 (3) | C1—P2—C31—C36 | −71.0 (8) |
P2—Cu2—P4—C2 | 25.2 (3) | Cu2—P2—C31—C36 | 167.3 (7) |
P3—Cu1—N1—C3 | 67.7 (6) | C36—C31—C32—C33 | 1.0 (17) |
P1—Cu1—N1—C3 | −91.2 (6) | P2—C31—C32—C33 | −175.1 (10) |
P3—Cu1—N1—C7 | −111.2 (6) | C31—C32—C33—C34 | −2 (2) |
P1—Cu1—N1—C7 | 89.8 (7) | C32—C33—C34—C35 | 2 (2) |
P2—Cu2—N2—C8 | −90.5 (6) | C33—C34—C35—C36 | 0 (2) |
P4—Cu2—N2—C8 | 103.8 (6) | C32—C31—C36—C35 | 0.5 (17) |
P2—Cu2—N2—C12 | 93.0 (6) | P2—C31—C36—C35 | 176.4 (10) |
P4—Cu2—N2—C12 | −72.7 (6) | C34—C35—C36—C31 | −1 (2) |
C25—P2—C1—P1 | 87.8 (4) | C43—P3—C37—C38 | 118.7 (6) |
C31—P2—C1—P1 | −162.0 (4) | C2—P3—C37—C38 | −131.2 (6) |
Cu2—P2—C1—P1 | −45.0 (4) | Cu1—P3—C37—C38 | 1.8 (7) |
C13—P1—C1—P2 | −74.7 (4) | C43—P3—C37—C42 | −62.0 (6) |
C19—P1—C1—P2 | 175.5 (3) | C2—P3—C37—C42 | 48.1 (6) |
Cu1—P1—C1—P2 | 61.7 (4) | Cu1—P3—C37—C42 | −178.9 (5) |
C55—P4—C2—P3 | −167.7 (4) | C42—C37—C38—C39 | 0.5 (12) |
C49—P4—C2—P3 | −57.6 (4) | P3—C37—C38—C39 | 179.8 (6) |
Cu2—P4—C2—P3 | 74.4 (4) | C37—C38—C39—C40 | −0.7 (14) |
C43—P3—C2—P4 | −161.3 (3) | C38—C39—C40—C41 | 0.0 (14) |
C37—P3—C2—P4 | 89.1 (4) | C39—C40—C41—C42 | 0.8 (14) |
Cu1—P3—C2—P4 | −46.3 (4) | C38—C37—C42—C41 | 0.3 (11) |
C7—N1—C3—C4 | −0.1 (11) | P3—C37—C42—C41 | −179.0 (6) |
Cu1—N1—C3—C4 | −179.1 (6) | C40—C41—C42—C37 | −1.0 (13) |
N1—C3—C4—C5 | 0.4 (12) | C37—P3—C43—C44 | 116.2 (6) |
C3—C4—C5—C6 | −0.9 (11) | C2—P3—C43—C44 | 7.2 (7) |
C3—C4—C5—C5i | −179.5 (8) | Cu1—P3—C43—C44 | −116.0 (6) |
C4—C5—C6—C7 | 1.2 (14) | C37—P3—C43—C48 | −66.9 (6) |
C5i—C5—C6—C7 | 179.8 (9) | C2—P3—C43—C48 | −175.9 (5) |
C3—N1—C7—C6 | 0.4 (14) | Cu1—P3—C43—C48 | 60.9 (5) |
Cu1—N1—C7—C6 | 179.5 (8) | C48—C43—C44—C45 | −0.9 (11) |
C5—C6—C7—N1 | −1.0 (17) | P3—C43—C44—C45 | 176.0 (6) |
C12—N2—C8—C9 | 0.5 (13) | C43—C44—C45—C46 | 1.2 (13) |
Cu2—N2—C8—C9 | −176.2 (7) | C44—C45—C46—C47 | −1.1 (14) |
N2—C8—C9—C10 | 0.9 (15) | C45—C46—C47—C48 | 0.8 (13) |
C8—C9—C10—C11 | −2.4 (13) | C46—C47—C48—C43 | −0.6 (12) |
C8—C9—C10—C10ii | 177.1 (9) | C44—C43—C48—C47 | 0.6 (10) |
C9—C10—C11—C12 | 2.5 (12) | P3—C43—C48—C47 | −176.5 (6) |
C10ii—C10—C11—C12 | −177.0 (9) | C55—P4—C49—C50 | −134.3 (6) |
C8—N2—C12—C11 | −0.4 (12) | C2—P4—C49—C50 | 116.4 (6) |
Cu2—N2—C12—C11 | 176.3 (6) | Cu2—P4—C49—C50 | −15.8 (7) |
C10—C11—C12—N2 | −1.2 (13) | C55—P4—C49—C54 | 45.5 (7) |
C19—P1—C13—C18 | 33.3 (7) | C2—P4—C49—C54 | −63.7 (7) |
C1—P1—C13—C18 | −75.4 (6) | Cu2—P4—C49—C54 | 164.0 (5) |
Cu1—P1—C13—C18 | 146.8 (5) | C54—C49—C50—C51 | −0.1 (12) |
C19—P1—C13—C14 | −146.3 (6) | P4—C49—C50—C51 | 179.7 (7) |
C1—P1—C13—C14 | 105.0 (6) | C49—C50—C51—C52 | 1.3 (15) |
Cu1—P1—C13—C14 | −32.8 (6) | C50—C51—C52—C53 | −2.0 (17) |
C18—C13—C14—C15 | −0.4 (11) | C51—C52—C53—C54 | 1.6 (16) |
P1—C13—C14—C15 | 179.1 (6) | C50—C49—C54—C53 | −0.3 (12) |
C13—C14—C15—C16 | 1.2 (14) | P4—C49—C54—C53 | 179.8 (6) |
C14—C15—C16—C17 | −0.7 (16) | C52—C53—C54—C49 | −0.4 (14) |
C15—C16—C17—C18 | −0.5 (16) | C49—P4—C55—C56 | 52.9 (7) |
C14—C13—C18—C17 | −0.7 (11) | C2—P4—C55—C56 | 164.2 (7) |
P1—C13—C18—C17 | 179.7 (7) | Cu2—P4—C55—C56 | −71.4 (7) |
C16—C17—C18—C13 | 1.2 (14) | C49—P4—C55—C60 | −135.1 (7) |
C13—P1—C19—C20 | −116.5 (6) | C2—P4—C55—C60 | −23.9 (7) |
C1—P1—C19—C20 | −6.4 (7) | Cu2—P4—C55—C60 | 100.6 (7) |
Cu1—P1—C19—C20 | 119.8 (6) | C60—C55—C56—C57 | −0.2 (13) |
C13—P1—C19—C24 | 69.0 (6) | P4—C55—C56—C57 | 172.2 (8) |
C1—P1—C19—C24 | 179.1 (5) | C55—C56—C57—C58 | 1.9 (18) |
Cu1—P1—C19—C24 | −54.7 (5) | C56—C57—C58—C59 | −2 (2) |
C24—C19—C20—C21 | 1.1 (11) | C57—C58—C59—C60 | 0 (2) |
P1—C19—C20—C21 | −173.4 (6) | C58—C59—C60—C55 | 2.2 (16) |
C19—C20—C21—C22 | −0.9 (13) | C56—C55—C60—C59 | −1.8 (13) |
C20—C21—C22—C23 | 0.0 (13) | P4—C55—C60—C59 | −173.9 (8) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C10H8N2)(C25H22P2)2](BF4)2·2.5CH2Cl2 |
Mr | 1437.93 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 10.9860 (12), 16.1541 (18), 20.336 (2) |
α, β, γ (°) | 82.821 (2), 89.030 (2), 74.237 (2) |
V (Å3) | 3445.5 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.22 × 0.12 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.871, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17673, 12068, 7620 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.231, 1.16 |
No. of reflections | 12068 |
No. of parameters | 802 |
No. of restraints | 142 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.14, −0.54 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).
Cu1—N1 | 2.018 (5) | Cu2—N2 | 2.022 (5) |
Cu1—P3 | 2.2329 (18) | Cu2—P2 | 2.2397 (19) |
Cu1—P1 | 2.2515 (18) | Cu2—P4 | 2.2505 (19) |
N1—Cu1—P3 | 118.66 (17) | N2—Cu2—P2 | 116.50 (18) |
N1—Cu1—P1 | 115.59 (17) | N2—Cu2—P4 | 111.90 (18) |
P3—Cu1—P1 | 122.10 (7) | P2—Cu2—P4 | 129.66 (7) |
Acknowledgements
The authors thank Henan Agricultural University and Heilongjiang August First Land Reclamation University for the generous support of this study.
References
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4,4'-bipyridine is widely used in the construction of transition metal coordination complexes, because of its rod-like shape, which allows the ligand to connect metal ions into an extended array (Park et al., 2001). The hydrocarbon backbone bisphosphine ligand Ph2PCH2PPh2 (dppm) has been widely studied and has shown great versatility as a ligand for its ability to bridge metal centers in the µ-bonding mode, forming bi- and polynuclear complexes (Ahuja et al., 2007; Sekabunga et al., 2002; Yam et al., 2001). Here, we report crystal structure of the title compound, (I), one-dimensional chain coordination polymer bridged by (diphenylphosphino)methane and 4,4'-bipyridine.
The Cu atom in (I) (Fig. 1) has a trigonal–planar coordination geometry involving the N atom of the 4,4'-bipyridine ligand and two P atoms of two (diphenylphosphino)methane ligands. A four-coordinate tetrahedral coordination sphere is more usual for CuI atoms and the trigonal–planar arrangement in the presen complex may reflect the large size of the rigid organic ligands which would spacially hinder any additional donor atoms from entering the metal coordination sphere. The Cu—N bonds lengths are 2.018 (5) and 2.022 (5) Å, while the Cu—P bonds are between 2.233 (2) and 2.252 (2) Å (Table 1). The two CuI ions in (I) are doubly bridged by two (diphenylphosphino)methane ligands and single bridged by 4,4'-bipyridine ligands. The Cu···Cu distance bridged by two (diphenylphosphino)methane is 3.732 (3) Å, much shorter than reported data, 4.720 (5)Å (Liu et al., 2006).