metal-organic compounds
[1,4-Bis(diphenylphosphanyl)butane-κ2P,P′]dibromidopalladium(II)
aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
*Correspondence e-mail: yssong@chonnam.ac.kr
In the title complex, [PdBr2(C28H28P2)], the PdII ion has a distorted cis-Br2P2 square-planar coordination geometry defined by two P atoms from the chelating 1,4-bis(diphenylphosphanyl)butane ligand and two Br− anions. The four phenyl rings are inclined to the least-squares plane of the PdBr2P2 unit [maximum deviation = 0.1294 (7) Å], making dihedral angles of 66.3 (2), 87.2 (2), 68.8 (2) and 86.8 (2)°. The butylene chain is in a gauche conformation, with a C—C—C—C torsion angle of 57.0 (8)°. Intermolecular C—H⋯Br hydrogen bonds link the complex molecules into supramolecular layers in the ab plane. Weak π–π interactions, both intra- and intermolecular [shortest inter-centroid distance = 4.598 (5) Å], are also noted in the three-dimensional architecture.
CCDC reference: 981207
Related literature
For the crystal structures of related [MCl2(dppb)] complexes where M = Pd or Pt, and dppb = 1,4-bis(diphenylphosphanyl)butane), see: Makhaev et al. (1996); Deacon et al. (2005).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 981207
10.1107/S1600536814000774/tk5286sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000774/tk5286Isup2.hkl
To a solution of K2PdBr4 (0.2526 g, 0.501 mmol) in MeOH (20 ml) was added 1,4-bis(diphenylphosphanyl)butane (0.2142 g, 0.502 mmol) followed by stirring for 3 h at room temperature. The formed precipitate was separated by filtration, washed with H2O and acetone, and dried at 323 K, to give a yellow powder (0.1412 g). Crystals were obtained by slow evaporation from its CH3NO2 solution held at room temperature.
The H atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.95 Å (CH) or 0.99 Å (CH2) and Uiso(H) = 1.2Ueq(C). The highest peak (1.13 e Å-3) and the deepest hole (-0.96 e Å-3) in the difference Fourier map are located 1.14 and 0.58 Å, respectively, from the Br1 atom. A large number of reflections were omitted from the final cycles of
owing to poor agreement.Crystal structures of the related chlorido PdII and PtII complexes, [PdCl2(dppb)] (dppb = 1,4-bis(diphenylphosphanyl)butane, C28H28P2) (Makhaev et al., 1996) and [PtCl2(dppb)] (Deacon et al., 2005) have been investigated previously.
The PdII ion in the title complex, [PdBr2(dppb)], has a distorted cis-Br2P2 square-planar coordination geometry defined by two P atoms from the chelating dppb ligand and two Br- anions (Fig. 1). The Pd—P and Pd—Br bond lengths are nearly equivalent, respectively (Table 1). In the crystal, the four phenyl rings are inclined to the least-squares plane of the PdBr2P2 unit [maximum deviation = 0.1294 (7) Å], making dihedral angles of 66.3 (2) (C1–C6), 87.2 (2) (C7–C12), 68.8 (2) (C17–C22) and 86.8 (2)° (C23–C28). The torsion angle for the four atoms within the butylene chain indicates that the chain is approximately in the π—π interactions between the benzene rings are present, the shortest ring centroid-centroid distance being 4.598 (5) Å (Fig. 2). Intermolecular C—H···Br hydrogen bonds further stabilize the (Table 2).
conformation [C13—C14—C15—C16 = 57.0 (8)°]. The complex molecules are stacked in columns along the a axis. In the columns, numerous intra- and intermolecularCrystal structures of the related chlorido PdII and PtII complexes, [PdCl2(dppb)] (dppb = 1,4-bis(diphenylphosphanyl)butane, C28H28P2) (Makhaev et al., 1996) and [PtCl2(dppb)] (Deacon et al., 2005) have been investigated previously.
The PdII ion in the title complex, [PdBr2(dppb)], has a distorted cis-Br2P2 square-planar coordination geometry defined by two P atoms from the chelating dppb ligand and two Br- anions (Fig. 1). The Pd—P and Pd—Br bond lengths are nearly equivalent, respectively (Table 1). In the crystal, the four phenyl rings are inclined to the least-squares plane of the PdBr2P2 unit [maximum deviation = 0.1294 (7) Å], making dihedral angles of 66.3 (2) (C1–C6), 87.2 (2) (C7–C12), 68.8 (2) (C17–C22) and 86.8 (2)° (C23–C28). The torsion angle for the four atoms within the butylene chain indicates that the chain is approximately in the π—π interactions between the benzene rings are present, the shortest ring centroid-centroid distance being 4.598 (5) Å (Fig. 2). Intermolecular C—H···Br hydrogen bonds further stabilize the (Table 2).
conformation [C13—C14—C15—C16 = 57.0 (8)°]. The complex molecules are stacked in columns along the a axis. In the columns, numerous intra- and intermolecularFor the crystal structures of related [MCl2(dppb)] complexes where M = Pd or Pt, and dppb = 1,4-bis(diphenylphosphanyl)butane), see: Makhaev et al. (1996); Deacon et al. (2005).
To a solution of K2PdBr4 (0.2526 g, 0.501 mmol) in MeOH (20 ml) was added 1,4-bis(diphenylphosphanyl)butane (0.2142 g, 0.502 mmol) followed by stirring for 3 h at room temperature. The formed precipitate was separated by filtration, washed with H2O and acetone, and dried at 323 K, to give a yellow powder (0.1412 g). Crystals were obtained by slow evaporation from its CH3NO2 solution held at room temperature.
detailsThe H atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.95 Å (CH) or 0.99 Å (CH2) and Uiso(H) = 1.2Ueq(C). The highest peak (1.13 e Å-3) and the deepest hole (-0.96 e Å-3) in the difference Fourier map are located 1.14 and 0.58 Å, respectively, from the Br1 atom. A large number of reflections were omitted from the final cycles of
owing to poor agreement.Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[PdBr2(C28H28P2)] | Z = 2 |
Mr = 692.66 | F(000) = 684 |
Triclinic, P1 | Dx = 1.786 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7481 (5) Å | Cell parameters from 3866 reflections |
b = 10.7677 (6) Å | θ = 2.4–26.0° |
c = 14.4789 (8) Å | µ = 3.96 mm−1 |
α = 87.203 (1)° | T = 200 K |
β = 79.389 (1)° | Block, yellow |
γ = 73.929 (1)° | 0.06 × 0.04 × 0.01 mm |
V = 1288.15 (13) Å3 |
Bruker SMART 1000 CCD diffractometer | 4961 independent reflections |
Radiation source: fine-focus sealed tube | 3847 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 26.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −8→10 |
Tmin = 0.859, Tmax = 1.000 | k = −12→13 |
8009 measured reflections | l = −17→17 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0398P)2 + 6.4613P] where P = (Fo2 + 2Fc2)/3 |
4961 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 1.13 e Å−3 |
0 restraints | Δρmin = −0.96 e Å−3 |
[PdBr2(C28H28P2)] | γ = 73.929 (1)° |
Mr = 692.66 | V = 1288.15 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.7481 (5) Å | Mo Kα radiation |
b = 10.7677 (6) Å | µ = 3.96 mm−1 |
c = 14.4789 (8) Å | T = 200 K |
α = 87.203 (1)° | 0.06 × 0.04 × 0.01 mm |
β = 79.389 (1)° |
Bruker SMART 1000 CCD diffractometer | 4961 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3847 reflections with I > 2σ(I) |
Tmin = 0.859, Tmax = 1.000 | Rint = 0.024 |
8009 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.13 e Å−3 |
4961 reflections | Δρmin = −0.96 e Å−3 |
298 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 | ||
Pd1 | 0.11465 (5) | 0.83898 (4) | 0.24341 (3) | 0.01959 (13) | |
Br1 | −0.02105 (8) | 0.66561 (7) | 0.27646 (5) | 0.03468 (19) | |
Br2 | −0.14937 (9) | 0.99359 (7) | 0.23280 (6) | 0.0411 (2) | |
P1 | 0.33484 (19) | 0.69181 (14) | 0.28150 (11) | 0.0216 (3) | |
P2 | 0.24181 (19) | 0.99889 (14) | 0.21058 (11) | 0.0204 (3) | |
C1 | 0.4032 (7) | 0.5406 (6) | 0.2161 (4) | 0.0241 (13) | |
C2 | 0.3474 (8) | 0.5242 (6) | 0.1356 (4) | 0.0272 (14) | |
H2 | 0.2631 | 0.5902 | 0.1155 | 0.033* | |
C3 | 0.4149 (9) | 0.4111 (7) | 0.0844 (5) | 0.0374 (17) | |
H3 | 0.3777 | 0.3997 | 0.0286 | 0.045* | |
C4 | 0.5372 (10) | 0.3136 (7) | 0.1143 (5) | 0.0409 (18) | |
H4 | 0.5824 | 0.2358 | 0.0791 | 0.049* | |
C5 | 0.5920 (9) | 0.3292 (7) | 0.1931 (6) | 0.0411 (18) | |
H5 | 0.6771 | 0.2631 | 0.2124 | 0.049* | |
C6 | 0.5244 (9) | 0.4414 (6) | 0.2458 (5) | 0.0371 (17) | |
H6 | 0.5607 | 0.4508 | 0.3023 | 0.044* | |
C7 | 0.2871 (7) | 0.6503 (6) | 0.4044 (4) | 0.0238 (13) | |
C8 | 0.2367 (9) | 0.5413 (7) | 0.4322 (5) | 0.0345 (16) | |
H8 | 0.2323 | 0.4829 | 0.3862 | 0.041* | |
C9 | 0.1921 (9) | 0.5164 (7) | 0.5277 (5) | 0.0372 (17) | |
H9 | 0.1606 | 0.4401 | 0.5467 | 0.045* | |
C10 | 0.1941 (9) | 0.6014 (8) | 0.5925 (5) | 0.0406 (18) | |
H10 | 0.1619 | 0.5844 | 0.6571 | 0.049* | |
C11 | 0.2413 (9) | 0.7116 (8) | 0.5679 (5) | 0.044 (2) | |
H11 | 0.2400 | 0.7705 | 0.6150 | 0.053* | |
C12 | 0.2918 (9) | 0.7370 (7) | 0.4721 (5) | 0.0378 (17) | |
H12 | 0.3282 | 0.8114 | 0.4540 | 0.045* | |
C13 | 0.5229 (7) | 0.7372 (6) | 0.2743 (4) | 0.0260 (14) | |
H13A | 0.4977 | 0.8243 | 0.3022 | 0.031* | |
H13B | 0.5929 | 0.6759 | 0.3124 | 0.031* | |
C14 | 0.6160 (7) | 0.7384 (7) | 0.1750 (5) | 0.0299 (15) | |
H14A | 0.7091 | 0.7731 | 0.1770 | 0.036* | |
H14B | 0.6599 | 0.6482 | 0.1521 | 0.036* | |
C15 | 0.5194 (8) | 0.8167 (6) | 0.1050 (4) | 0.0276 (14) | |
H15A | 0.5917 | 0.8128 | 0.0433 | 0.033* | |
H15B | 0.4337 | 0.7762 | 0.0974 | 0.033* | |
C16 | 0.4422 (8) | 0.9557 (6) | 0.1317 (5) | 0.0299 (14) | |
H16A | 0.4311 | 1.0058 | 0.0729 | 0.036* | |
H16B | 0.5183 | 0.9856 | 0.1620 | 0.036* | |
C17 | 0.1346 (8) | 1.1362 (6) | 0.1468 (4) | 0.0252 (14) | |
C18 | 0.1042 (9) | 1.1129 (7) | 0.0585 (5) | 0.0328 (15) | |
H18 | 0.1355 | 1.0271 | 0.0348 | 0.039* | |
C19 | 0.0289 (9) | 1.2140 (8) | 0.0056 (5) | 0.0402 (18) | |
H19 | 0.0089 | 1.1982 | −0.0545 | 0.048* | |
C20 | −0.0162 (9) | 1.3367 (7) | 0.0406 (5) | 0.0385 (18) | |
H20 | −0.0684 | 1.4060 | 0.0043 | 0.046* | |
C21 | 0.0120 (9) | 1.3630 (7) | 0.1278 (5) | 0.0381 (17) | |
H21 | −0.0202 | 1.4491 | 0.1510 | 0.046* | |
C22 | 0.0887 (8) | 1.2603 (6) | 0.1812 (5) | 0.0303 (15) | |
H22 | 0.1090 | 1.2765 | 0.2411 | 0.036* | |
C23 | 0.2624 (8) | 1.0629 (5) | 0.3199 (4) | 0.0237 (13) | |
C24 | 0.3971 (11) | 1.0970 (11) | 0.3321 (6) | 0.066 (3) | |
H24 | 0.4852 | 1.0889 | 0.2813 | 0.079* | |
C25 | 0.4052 (12) | 1.1432 (12) | 0.4179 (7) | 0.082 (4) | |
H25 | 0.4983 | 1.1682 | 0.4252 | 0.099* | |
C26 | 0.2834 (10) | 1.1533 (8) | 0.4913 (6) | 0.047 (2) | |
H26 | 0.2932 | 1.1811 | 0.5507 | 0.057* | |
C27 | 0.1464 (10) | 1.1238 (8) | 0.4807 (5) | 0.050 (2) | |
H27 | 0.0574 | 1.1353 | 0.5312 | 0.060* | |
C28 | 0.1389 (9) | 1.0763 (8) | 0.3940 (5) | 0.046 (2) | |
H28 | 0.0449 | 1.0527 | 0.3868 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.0200 (2) | 0.0182 (2) | 0.0209 (2) | −0.00528 (18) | −0.00436 (18) | 0.00072 (17) |
Br1 | 0.0327 (4) | 0.0324 (4) | 0.0422 (4) | −0.0135 (3) | −0.0096 (3) | 0.0062 (3) |
Br2 | 0.0281 (4) | 0.0293 (4) | 0.0630 (5) | −0.0029 (3) | −0.0091 (3) | 0.0027 (3) |
P1 | 0.0231 (8) | 0.0191 (7) | 0.0231 (8) | −0.0048 (6) | −0.0079 (6) | 0.0026 (6) |
P2 | 0.0231 (8) | 0.0182 (7) | 0.0192 (8) | −0.0064 (6) | −0.0013 (6) | 0.0006 (6) |
C1 | 0.022 (3) | 0.024 (3) | 0.024 (3) | −0.001 (3) | −0.005 (3) | 0.001 (2) |
C2 | 0.027 (3) | 0.023 (3) | 0.028 (3) | −0.003 (3) | −0.001 (3) | 0.002 (3) |
C3 | 0.044 (4) | 0.033 (4) | 0.034 (4) | −0.009 (3) | −0.006 (3) | −0.005 (3) |
C4 | 0.056 (5) | 0.025 (3) | 0.037 (4) | −0.014 (3) | 0.010 (4) | −0.013 (3) |
C5 | 0.030 (4) | 0.031 (4) | 0.051 (5) | 0.007 (3) | −0.002 (3) | 0.005 (3) |
C6 | 0.039 (4) | 0.024 (3) | 0.047 (4) | −0.001 (3) | −0.018 (3) | 0.000 (3) |
C7 | 0.021 (3) | 0.028 (3) | 0.019 (3) | −0.001 (3) | −0.006 (2) | −0.004 (2) |
C8 | 0.043 (4) | 0.032 (4) | 0.029 (4) | −0.010 (3) | −0.009 (3) | 0.005 (3) |
C9 | 0.039 (4) | 0.038 (4) | 0.034 (4) | −0.011 (3) | −0.005 (3) | 0.013 (3) |
C10 | 0.033 (4) | 0.059 (5) | 0.024 (4) | −0.009 (4) | −0.001 (3) | 0.016 (3) |
C11 | 0.043 (4) | 0.069 (5) | 0.018 (3) | −0.008 (4) | −0.007 (3) | −0.011 (3) |
C12 | 0.037 (4) | 0.043 (4) | 0.036 (4) | −0.013 (3) | −0.012 (3) | 0.002 (3) |
C13 | 0.026 (3) | 0.030 (3) | 0.026 (3) | −0.010 (3) | −0.012 (3) | 0.008 (3) |
C14 | 0.012 (3) | 0.037 (4) | 0.037 (4) | −0.001 (3) | −0.004 (3) | 0.001 (3) |
C15 | 0.022 (3) | 0.036 (4) | 0.023 (3) | −0.009 (3) | 0.004 (3) | 0.001 (3) |
C16 | 0.030 (4) | 0.032 (3) | 0.028 (3) | −0.012 (3) | −0.001 (3) | 0.007 (3) |
C17 | 0.033 (4) | 0.021 (3) | 0.022 (3) | −0.010 (3) | −0.007 (3) | 0.012 (2) |
C18 | 0.042 (4) | 0.031 (4) | 0.028 (4) | −0.012 (3) | −0.010 (3) | 0.002 (3) |
C19 | 0.043 (4) | 0.056 (5) | 0.029 (4) | −0.020 (4) | −0.013 (3) | 0.003 (3) |
C20 | 0.042 (4) | 0.035 (4) | 0.047 (4) | −0.020 (3) | −0.019 (4) | 0.025 (3) |
C21 | 0.041 (4) | 0.023 (3) | 0.051 (5) | −0.007 (3) | −0.012 (4) | 0.004 (3) |
C22 | 0.036 (4) | 0.028 (3) | 0.029 (4) | −0.013 (3) | −0.005 (3) | 0.000 (3) |
C23 | 0.030 (3) | 0.017 (3) | 0.024 (3) | −0.002 (3) | −0.007 (3) | −0.002 (2) |
C24 | 0.048 (5) | 0.123 (9) | 0.043 (5) | −0.054 (6) | 0.001 (4) | −0.022 (5) |
C25 | 0.062 (6) | 0.152 (11) | 0.058 (6) | −0.071 (7) | 0.001 (5) | −0.037 (7) |
C26 | 0.059 (5) | 0.049 (5) | 0.036 (4) | −0.007 (4) | −0.021 (4) | −0.014 (4) |
C27 | 0.048 (5) | 0.068 (6) | 0.033 (4) | −0.019 (4) | 0.004 (4) | −0.023 (4) |
C28 | 0.036 (4) | 0.073 (6) | 0.036 (4) | −0.029 (4) | 0.001 (3) | −0.018 (4) |
Pd1—P1 | 2.2676 (16) | C13—H13A | 0.9900 |
Pd1—P2 | 2.2834 (16) | C13—H13B | 0.9900 |
Pd1—Br1 | 2.4604 (8) | C14—C15 | 1.514 (9) |
Pd1—Br2 | 2.4712 (8) | C14—H14A | 0.9900 |
P1—C7 | 1.814 (6) | C14—H14B | 0.9900 |
P1—C1 | 1.819 (6) | C15—C16 | 1.499 (9) |
P1—C13 | 1.826 (6) | C15—H15A | 0.9900 |
P2—C23 | 1.816 (6) | C15—H15B | 0.9900 |
P2—C17 | 1.827 (6) | C16—H16A | 0.9900 |
P2—C16 | 1.860 (7) | C16—H16B | 0.9900 |
C1—C2 | 1.381 (9) | C17—C22 | 1.374 (9) |
C1—C6 | 1.395 (9) | C17—C18 | 1.401 (9) |
C2—C3 | 1.383 (9) | C18—C19 | 1.383 (10) |
C2—H2 | 0.9500 | C18—H18 | 0.9500 |
C3—C4 | 1.392 (10) | C19—C20 | 1.364 (10) |
C3—H3 | 0.9500 | C19—H19 | 0.9500 |
C4—C5 | 1.350 (11) | C20—C21 | 1.387 (10) |
C4—H4 | 0.9500 | C20—H20 | 0.9500 |
C5—C6 | 1.386 (10) | C21—C22 | 1.403 (9) |
C5—H5 | 0.9500 | C21—H21 | 0.9500 |
C6—H6 | 0.9500 | C22—H22 | 0.9500 |
C7—C8 | 1.382 (9) | C23—C28 | 1.357 (9) |
C7—C12 | 1.400 (9) | C23—C24 | 1.369 (10) |
C8—C9 | 1.399 (9) | C24—C25 | 1.382 (12) |
C8—H8 | 0.9500 | C24—H24 | 0.9500 |
C9—C10 | 1.349 (11) | C25—C26 | 1.344 (12) |
C9—H9 | 0.9500 | C25—H25 | 0.9500 |
C10—C11 | 1.371 (11) | C26—C27 | 1.358 (11) |
C10—H10 | 0.9500 | C26—H26 | 0.9500 |
C11—C12 | 1.414 (10) | C27—C28 | 1.397 (10) |
C11—H11 | 0.9500 | C27—H27 | 0.9500 |
C12—H12 | 0.9500 | C28—H28 | 0.9500 |
C13—C14 | 1.518 (9) | ||
P1—Pd1—P2 | 94.32 (6) | C14—C13—H13B | 108.8 |
P1—Pd1—Br1 | 85.65 (4) | P1—C13—H13B | 108.8 |
P2—Pd1—Br1 | 179.19 (5) | H13A—C13—H13B | 107.7 |
P1—Pd1—Br2 | 169.15 (5) | C15—C14—C13 | 115.2 (5) |
P2—Pd1—Br2 | 91.00 (4) | C15—C14—H14A | 108.5 |
Br1—Pd1—Br2 | 89.15 (3) | C13—C14—H14A | 108.5 |
C7—P1—C1 | 106.6 (3) | C15—C14—H14B | 108.5 |
C7—P1—C13 | 103.2 (3) | C13—C14—H14B | 108.5 |
C1—P1—C13 | 101.9 (3) | H14A—C14—H14B | 107.5 |
C7—P1—Pd1 | 108.0 (2) | C16—C15—C14 | 114.5 (6) |
C1—P1—Pd1 | 116.4 (2) | C16—C15—H15A | 108.6 |
C13—P1—Pd1 | 119.3 (2) | C14—C15—H15A | 108.6 |
C23—P2—C17 | 106.4 (3) | C16—C15—H15B | 108.6 |
C23—P2—C16 | 109.1 (3) | C14—C15—H15B | 108.6 |
C17—P2—C16 | 100.2 (3) | H15A—C15—H15B | 107.6 |
C23—P2—Pd1 | 109.2 (2) | C15—C16—P2 | 118.6 (4) |
C17—P2—Pd1 | 114.5 (2) | C15—C16—H16A | 107.7 |
C16—P2—Pd1 | 116.8 (2) | P2—C16—H16A | 107.7 |
C2—C1—C6 | 119.5 (6) | C15—C16—H16B | 107.7 |
C2—C1—P1 | 122.4 (5) | P2—C16—H16B | 107.7 |
C6—C1—P1 | 118.0 (5) | H16A—C16—H16B | 107.1 |
C1—C2—C3 | 119.6 (6) | C22—C17—C18 | 119.8 (6) |
C1—C2—H2 | 120.2 | C22—C17—P2 | 122.2 (5) |
C3—C2—H2 | 120.2 | C18—C17—P2 | 118.0 (5) |
C2—C3—C4 | 120.2 (7) | C19—C18—C17 | 120.4 (6) |
C2—C3—H3 | 119.9 | C19—C18—H18 | 119.8 |
C4—C3—H3 | 119.9 | C17—C18—H18 | 119.8 |
C5—C4—C3 | 120.4 (6) | C20—C19—C18 | 119.2 (7) |
C5—C4—H4 | 119.8 | C20—C19—H19 | 120.4 |
C3—C4—H4 | 119.8 | C18—C19—H19 | 120.4 |
C4—C5—C6 | 120.1 (7) | C19—C20—C21 | 121.8 (6) |
C4—C5—H5 | 119.9 | C19—C20—H20 | 119.1 |
C6—C5—H5 | 119.9 | C21—C20—H20 | 119.1 |
C5—C6—C1 | 120.2 (7) | C20—C21—C22 | 118.9 (6) |
C5—C6—H6 | 119.9 | C20—C21—H21 | 120.6 |
C1—C6—H6 | 119.9 | C22—C21—H21 | 120.6 |
C8—C7—C12 | 119.8 (6) | C17—C22—C21 | 119.9 (6) |
C8—C7—P1 | 122.0 (5) | C17—C22—H22 | 120.0 |
C12—C7—P1 | 118.1 (5) | C21—C22—H22 | 120.0 |
C7—C8—C9 | 120.3 (6) | C28—C23—C24 | 118.1 (6) |
C7—C8—H8 | 119.8 | C28—C23—P2 | 118.4 (5) |
C9—C8—H8 | 119.8 | C24—C23—P2 | 123.5 (6) |
C10—C9—C8 | 119.6 (7) | C23—C24—C25 | 120.2 (8) |
C10—C9—H9 | 120.2 | C23—C24—H24 | 119.9 |
C8—C9—H9 | 120.2 | C25—C24—H24 | 119.9 |
C9—C10—C11 | 121.9 (6) | C26—C25—C24 | 121.0 (8) |
C9—C10—H10 | 119.1 | C26—C25—H25 | 119.5 |
C11—C10—H10 | 119.1 | C24—C25—H25 | 119.5 |
C10—C11—C12 | 119.6 (7) | C25—C26—C27 | 120.1 (7) |
C10—C11—H11 | 120.2 | C25—C26—H26 | 119.9 |
C12—C11—H11 | 120.2 | C27—C26—H26 | 119.9 |
C7—C12—C11 | 118.7 (7) | C26—C27—C28 | 118.7 (7) |
C7—C12—H12 | 120.6 | C26—C27—H27 | 120.7 |
C11—C12—H12 | 120.6 | C28—C27—H27 | 120.7 |
C14—C13—P1 | 114.0 (4) | C23—C28—C27 | 121.7 (7) |
C14—C13—H13A | 108.8 | C23—C28—H28 | 119.1 |
P1—C13—H13A | 108.8 | C27—C28—H28 | 119.1 |
P2—Pd1—P1—C7 | 116.6 (2) | C9—C10—C11—C12 | −1.0 (11) |
Br1—Pd1—P1—C7 | −64.2 (2) | C8—C7—C12—C11 | −1.2 (10) |
Br2—Pd1—P1—C7 | −2.6 (4) | P1—C7—C12—C11 | 174.5 (5) |
P2—Pd1—P1—C1 | −123.6 (2) | C10—C11—C12—C7 | 2.1 (11) |
Br1—Pd1—P1—C1 | 55.6 (2) | C7—P1—C13—C14 | 162.9 (5) |
Br2—Pd1—P1—C1 | 117.2 (3) | C1—P1—C13—C14 | 52.4 (5) |
P2—Pd1—P1—C13 | −0.7 (2) | Pd1—P1—C13—C14 | −77.4 (5) |
Br1—Pd1—P1—C13 | 178.5 (2) | P1—C13—C14—C15 | 52.1 (7) |
Br2—Pd1—P1—C13 | −119.9 (3) | C13—C14—C15—C16 | 57.0 (8) |
P1—Pd1—P2—C23 | −75.1 (2) | C14—C15—C16—P2 | −85.3 (6) |
Br1—Pd1—P2—C23 | −163 (3) | C23—P2—C16—C15 | 115.9 (5) |
Br2—Pd1—P2—C23 | 95.4 (2) | C17—P2—C16—C15 | −132.6 (5) |
P1—Pd1—P2—C17 | 165.7 (2) | Pd1—P2—C16—C15 | −8.3 (6) |
Br1—Pd1—P2—C17 | 77 (3) | C23—P2—C17—C22 | 1.6 (6) |
Br2—Pd1—P2—C17 | −23.8 (2) | C16—P2—C17—C22 | −111.9 (6) |
P1—Pd1—P2—C16 | 49.1 (2) | Pd1—P2—C17—C22 | 122.3 (5) |
Br1—Pd1—P2—C16 | −39 (3) | C23—P2—C17—C18 | 179.4 (5) |
Br2—Pd1—P2—C16 | −140.4 (2) | C16—P2—C17—C18 | 65.9 (6) |
C7—P1—C1—C2 | 133.2 (5) | Pd1—P2—C17—C18 | −59.9 (6) |
C13—P1—C1—C2 | −118.9 (6) | C22—C17—C18—C19 | 0.3 (10) |
Pd1—P1—C1—C2 | 12.7 (6) | P2—C17—C18—C19 | −177.6 (6) |
C7—P1—C1—C6 | −51.2 (6) | C17—C18—C19—C20 | −0.4 (11) |
C13—P1—C1—C6 | 56.7 (6) | C18—C19—C20—C21 | 0.3 (12) |
Pd1—P1—C1—C6 | −171.7 (5) | C19—C20—C21—C22 | −0.1 (11) |
C6—C1—C2—C3 | −1.5 (10) | C18—C17—C22—C21 | −0.1 (10) |
P1—C1—C2—C3 | 174.1 (5) | P2—C17—C22—C21 | 177.6 (5) |
C1—C2—C3—C4 | 0.7 (10) | C20—C21—C22—C17 | 0.1 (11) |
C2—C3—C4—C5 | −0.6 (11) | C17—P2—C23—C28 | 85.7 (6) |
C3—C4—C5—C6 | 1.3 (12) | C16—P2—C23—C28 | −167.1 (6) |
C4—C5—C6—C1 | −2.2 (12) | Pd1—P2—C23—C28 | −38.4 (6) |
C2—C1—C6—C5 | 2.2 (11) | C17—P2—C23—C24 | −95.2 (7) |
P1—C1—C6—C5 | −173.5 (6) | C16—P2—C23—C24 | 12.1 (8) |
C1—P1—C7—C8 | −28.5 (6) | Pd1—P2—C23—C24 | 140.7 (7) |
C13—P1—C7—C8 | −135.4 (6) | C28—C23—C24—C25 | 0.2 (15) |
Pd1—P1—C7—C8 | 97.3 (5) | P2—C23—C24—C25 | −178.9 (8) |
C1—P1—C7—C12 | 155.9 (5) | C23—C24—C25—C26 | 1.2 (18) |
C13—P1—C7—C12 | 48.9 (6) | C24—C25—C26—C27 | −3.2 (17) |
Pd1—P1—C7—C12 | −78.3 (5) | C25—C26—C27—C28 | 3.5 (14) |
C12—C7—C8—C9 | −0.7 (10) | C24—C23—C28—C27 | 0.3 (13) |
P1—C7—C8—C9 | −176.3 (5) | P2—C23—C28—C27 | 179.4 (7) |
C7—C8—C9—C10 | 1.9 (11) | C26—C27—C28—C23 | −2.1 (13) |
C8—C9—C10—C11 | −1.0 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Br2i | 0.95 | 2.91 | 3.776 (7) | 153 |
C14—H14A···Br1ii | 0.99 | 2.93 | 3.617 (6) | 128 |
Symmetry codes: (i) x+1, y−1, z; (ii) x+1, y, z. |
Pd1—P1 | 2.2676 (16) | Pd1—Br1 | 2.4604 (8) |
Pd1—P2 | 2.2834 (16) | Pd1—Br2 | 2.4712 (8) |
P1—Pd1—P2 | 94.32 (6) | Br1—Pd1—Br2 | 89.15 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Br2i | 0.95 | 2.91 | 3.776 (7) | 153 |
C14—H14A···Br1ii | 0.99 | 2.93 | 3.617 (6) | 128 |
Symmetry codes: (i) x+1, y−1, z; (ii) x+1, y, z. |
Acknowledgements
This study was financially supported by Chonnam National University, 2009.
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