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metal-organic compounds
The title compound, [Pd2Cl2(μ-C6H5Se)2(C18H15P)2], crystallizes as a centrosymmetric phenylselenolato-bridged dinuclear palladium complex. The Pd atom shows a slightly distorted square-planar coordination geometry, with the Pd—Se distance trans to the terminal Cl− ligand at 2.4174 (6) Å and that trans to the triphenyl phospine at 2.4748 (7) Å. These values are consistent with the relative trans influence of Cl− and PPh3. The terminal Cl− ligands are in trans positions with respect to each other.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000960/fl6080sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000960/fl6080Isup2.hkl |
CCDC reference: 234821
Key indicators
- Single-crystal X-ray study
- T = 150 K
- R factor = 0.038
- wR factor = 0.094
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pd1 - Se1 = 8.37 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).
Di-µ-phenylselenolato-bis[chloro(triphenylphosphine)palladium(II)] top
Crystal data top
[Pd2Cl2(C6H5Se)2(C18H15P)2] | F(000) = 1104 |
Mr = 1120.36 | Dx = 1.724 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4136 reflections |
a = 8.878 (2) Å | θ = 3.8–27.5° |
b = 17.533 (4) Å | µ = 2.75 mm−1 |
c = 14.398 (3) Å | T = 150 K |
β = 105.60 (3)° | Needle, orange |
V = 2158.7 (9) Å3 | 0.25 × 0.15 × 0.08 mm |
Z = 2 |
Data collection top
Bruker-Nonius KappaCCD area-detector diffractometer | 4914 independent reflections |
Radiation source: fine-focus sealed tube | 4136 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.8° |
Absorption correction: psi scan (SHELXTL; Bruker, 2001) | h = −11→11 |
Tmin = 0.546, Tmax = 0.810 | k = −22→22 |
23990 measured reflections | l = −18→18 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.034P)2 + 3.9989P] where P = (Fo2 + 2Fc2)/3 |
4914 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.91 e Å−3 |
0 restraints | Δρmin = −0.94 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Pd1 | 0.48993 (3) | 0.451527 (15) | 0.110794 (19) | 0.02584 (9) | |
Se1 | 0.53919 (4) | 0.57869 (2) | 0.06105 (3) | 0.02807 (11) | |
Cl1 | 0.39683 (13) | 0.32927 (5) | 0.12931 (7) | 0.0404 (2) | |
P1 | 0.51096 (11) | 0.48003 (5) | 0.27025 (7) | 0.0260 (2) | |
C1 | 0.3337 (5) | 0.6171 (2) | 0.0582 (3) | 0.0304 (8) | |
C2 | 0.3213 (5) | 0.6758 (2) | 0.1203 (3) | 0.0376 (9) | |
H2 | 0.4127 | 0.6996 | 0.1592 | 0.045* | |
C3 | 0.1743 (6) | 0.6995 (3) | 0.1252 (3) | 0.0465 (11) | |
H3 | 0.1656 | 0.7389 | 0.1688 | 0.056* | |
C4 | 0.0408 (6) | 0.6663 (3) | 0.0673 (4) | 0.0482 (11) | |
H4 | −0.0590 | 0.6827 | 0.0716 | 0.058* | |
C5 | 0.0517 (5) | 0.6097 (3) | 0.0037 (3) | 0.0433 (10) | |
H5 | −0.0405 | 0.5879 | −0.0371 | 0.052* | |
C6 | 0.1972 (5) | 0.5845 (2) | −0.0010 (3) | 0.0361 (9) | |
H6 | 0.2047 | 0.5449 | −0.0445 | 0.043* | |
C111 | 0.3241 (4) | 0.4603 (2) | 0.2925 (3) | 0.0308 (8) | |
C112 | 0.3073 (5) | 0.4089 (2) | 0.3635 (3) | 0.0420 (10) | |
H112 | 0.3974 | 0.3864 | 0.4055 | 0.050* | |
C113 | 0.1617 (6) | 0.3909 (3) | 0.3726 (5) | 0.0589 (14) | |
H113 | 0.1506 | 0.3562 | 0.4210 | 0.071* | |
C114 | 0.0312 (6) | 0.4238 (3) | 0.3109 (5) | 0.0628 (15) | |
H114 | −0.0697 | 0.4100 | 0.3159 | 0.075* | |
C115 | 0.0448 (5) | 0.4767 (3) | 0.2416 (4) | 0.0533 (12) | |
H115 | −0.0456 | 0.5005 | 0.2015 | 0.064* | |
C116 | 0.1913 (5) | 0.4942 (3) | 0.2318 (3) | 0.0408 (9) | |
H116 | 0.2019 | 0.5293 | 0.1837 | 0.049* | |
C121 | 0.5578 (4) | 0.5782 (2) | 0.3091 (3) | 0.0291 (8) | |
C122 | 0.4626 (5) | 0.6217 (2) | 0.3509 (3) | 0.0371 (9) | |
H122 | 0.3703 | 0.6002 | 0.3615 | 0.045* | |
C123 | 0.5034 (6) | 0.6970 (3) | 0.3773 (3) | 0.0490 (12) | |
H123 | 0.4373 | 0.7271 | 0.4045 | 0.059* | |
C124 | 0.6379 (6) | 0.7278 (3) | 0.3643 (3) | 0.0515 (12) | |
H124 | 0.6645 | 0.7791 | 0.3828 | 0.062* | |
C125 | 0.7350 (5) | 0.6850 (3) | 0.3246 (3) | 0.0445 (11) | |
H125 | 0.8286 | 0.7066 | 0.3164 | 0.053* | |
C126 | 0.6954 (5) | 0.6100 (2) | 0.2967 (3) | 0.0351 (8) | |
H126 | 0.7621 | 0.5804 | 0.2691 | 0.042* | |
C131 | 0.6529 (4) | 0.4239 (2) | 0.3593 (3) | 0.0311 (8) | |
C132 | 0.7394 (5) | 0.4577 (3) | 0.4454 (3) | 0.0421 (10) | |
H132 | 0.7254 | 0.5101 | 0.4575 | 0.051* | |
C133 | 0.8464 (6) | 0.4138 (3) | 0.5132 (3) | 0.0491 (11) | |
H133 | 0.9056 | 0.4367 | 0.5715 | 0.059* | |
C134 | 0.8667 (5) | 0.3384 (3) | 0.4967 (4) | 0.0508 (12) | |
H134 | 0.9396 | 0.3090 | 0.5434 | 0.061* | |
C135 | 0.7829 (5) | 0.3050 (2) | 0.4135 (4) | 0.0489 (12) | |
H135 | 0.7969 | 0.2523 | 0.4028 | 0.059* | |
C136 | 0.6759 (5) | 0.3478 (2) | 0.3435 (3) | 0.0405 (10) | |
H136 | 0.6193 | 0.3243 | 0.2850 | 0.049* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.03095 (16) | 0.02140 (15) | 0.02557 (15) | 0.00068 (10) | 0.00831 (11) | −0.00079 (10) |
Se1 | 0.0346 (2) | 0.02377 (19) | 0.02576 (19) | −0.00179 (14) | 0.00805 (15) | −0.00162 (13) |
Cl1 | 0.0582 (6) | 0.0261 (5) | 0.0378 (5) | −0.0077 (4) | 0.0145 (5) | −0.0022 (4) |
P1 | 0.0287 (5) | 0.0231 (4) | 0.0268 (5) | −0.0002 (4) | 0.0085 (4) | −0.0001 (4) |
C1 | 0.039 (2) | 0.0252 (18) | 0.0281 (19) | 0.0037 (15) | 0.0112 (16) | 0.0022 (14) |
C2 | 0.051 (2) | 0.029 (2) | 0.033 (2) | 0.0064 (17) | 0.0112 (18) | −0.0002 (16) |
C3 | 0.061 (3) | 0.033 (2) | 0.048 (3) | 0.012 (2) | 0.020 (2) | 0.0011 (19) |
C4 | 0.048 (3) | 0.048 (3) | 0.052 (3) | 0.017 (2) | 0.019 (2) | 0.008 (2) |
C5 | 0.040 (2) | 0.042 (2) | 0.045 (2) | 0.0056 (19) | 0.0063 (19) | 0.008 (2) |
C6 | 0.045 (2) | 0.030 (2) | 0.030 (2) | 0.0053 (17) | 0.0071 (17) | 0.0017 (15) |
C111 | 0.0314 (19) | 0.0295 (19) | 0.034 (2) | −0.0043 (15) | 0.0134 (16) | −0.0087 (15) |
C112 | 0.044 (2) | 0.034 (2) | 0.054 (3) | 0.0032 (18) | 0.025 (2) | 0.0045 (19) |
C113 | 0.059 (3) | 0.043 (3) | 0.090 (4) | −0.001 (2) | 0.048 (3) | 0.007 (3) |
C114 | 0.045 (3) | 0.067 (3) | 0.086 (4) | −0.016 (3) | 0.036 (3) | −0.015 (3) |
C115 | 0.033 (2) | 0.075 (4) | 0.051 (3) | −0.002 (2) | 0.010 (2) | −0.018 (3) |
C116 | 0.035 (2) | 0.054 (3) | 0.033 (2) | −0.0017 (19) | 0.0088 (17) | −0.0048 (18) |
C121 | 0.0326 (19) | 0.0279 (18) | 0.0253 (18) | −0.0006 (15) | 0.0052 (15) | 0.0017 (14) |
C122 | 0.043 (2) | 0.036 (2) | 0.032 (2) | 0.0002 (17) | 0.0081 (17) | −0.0083 (16) |
C123 | 0.066 (3) | 0.036 (2) | 0.043 (3) | 0.005 (2) | 0.011 (2) | −0.0151 (19) |
C124 | 0.071 (3) | 0.029 (2) | 0.048 (3) | −0.011 (2) | 0.005 (2) | −0.0108 (19) |
C125 | 0.047 (2) | 0.041 (2) | 0.039 (2) | −0.0156 (19) | −0.0002 (19) | −0.0006 (19) |
C126 | 0.037 (2) | 0.032 (2) | 0.032 (2) | −0.0011 (16) | 0.0028 (16) | 0.0001 (16) |
C131 | 0.0311 (19) | 0.0308 (19) | 0.031 (2) | 0.0015 (15) | 0.0078 (15) | 0.0086 (15) |
C132 | 0.051 (3) | 0.043 (2) | 0.031 (2) | 0.0042 (19) | 0.0085 (18) | 0.0047 (17) |
C133 | 0.047 (3) | 0.062 (3) | 0.033 (2) | 0.002 (2) | 0.0012 (19) | 0.009 (2) |
C134 | 0.042 (2) | 0.051 (3) | 0.053 (3) | −0.002 (2) | 0.003 (2) | 0.028 (2) |
C135 | 0.036 (2) | 0.029 (2) | 0.077 (3) | 0.0002 (17) | 0.009 (2) | 0.022 (2) |
C136 | 0.032 (2) | 0.032 (2) | 0.054 (3) | −0.0033 (16) | 0.0063 (19) | 0.0066 (18) |
Geometric parameters (Å, º) top
Pd1—P1 | 2.3075 (10) | C114—H114 | 0.9500 |
Pd1—Cl1 | 2.3383 (11) | C115—C116 | 1.380 (6) |
Pd1—Se1 | 2.4174 (6) | C115—H115 | 0.9500 |
Pd1—Se1i | 2.4748 (7) | C116—H116 | 0.9500 |
Se1—C1 | 1.935 (4) | C121—C122 | 1.390 (6) |
Se1—Pd1i | 2.4748 (7) | C121—C126 | 1.398 (5) |
P1—C111 | 1.806 (4) | C122—C123 | 1.394 (6) |
P1—C121 | 1.823 (4) | C122—H122 | 0.9500 |
P1—C131 | 1.825 (4) | C123—C124 | 1.368 (7) |
C1—C2 | 1.386 (5) | C123—H123 | 0.9500 |
C1—C6 | 1.402 (6) | C124—C125 | 1.377 (7) |
C2—C3 | 1.389 (6) | C124—H124 | 0.9500 |
C2—H2 | 0.9500 | C125—C126 | 1.393 (6) |
C3—C4 | 1.381 (7) | C125—H125 | 0.9500 |
C3—H3 | 0.9500 | C126—H126 | 0.9500 |
C4—C5 | 1.371 (7) | C131—C136 | 1.379 (6) |
C4—H4 | 0.9500 | C131—C132 | 1.401 (6) |
C5—C6 | 1.384 (6) | C132—C133 | 1.396 (6) |
C5—H5 | 0.9500 | C132—H132 | 0.9500 |
C6—H6 | 0.9500 | C133—C134 | 1.365 (7) |
C111—C116 | 1.398 (6) | C133—H133 | 0.9500 |
C111—C112 | 1.399 (6) | C134—C135 | 1.361 (7) |
C112—C113 | 1.371 (6) | C134—H134 | 0.9500 |
C112—H112 | 0.9500 | C135—C136 | 1.402 (6) |
C113—C114 | 1.382 (8) | C135—H135 | 0.9500 |
C113—H113 | 0.9500 | C136—H136 | 0.9500 |
C114—C115 | 1.391 (8) | ||
P1—Pd1—Cl1 | 91.24 (4) | C115—C114—H114 | 119.3 |
P1—Pd1—Se1 | 97.03 (3) | C116—C115—C114 | 119.2 (5) |
Cl1—Pd1—Se1 | 167.67 (3) | C116—C115—H115 | 120.4 |
P1—Pd1—Se1i | 178.69 (3) | C114—C115—H115 | 120.4 |
Cl1—Pd1—Se1i | 88.43 (3) | C115—C116—C111 | 120.1 (4) |
Se1—Pd1—Se1i | 83.098 (18) | C115—C116—H116 | 120.0 |
C1—Se1—Pd1 | 94.73 (11) | C111—C116—H116 | 120.0 |
C1—Se1—Pd1i | 102.07 (12) | C122—C121—C126 | 119.4 (4) |
Pd1—Se1—Pd1i | 96.902 (18) | C122—C121—P1 | 122.4 (3) |
C111—P1—C121 | 105.71 (17) | C126—C121—P1 | 118.2 (3) |
C111—P1—C131 | 105.43 (18) | C121—C122—C123 | 119.6 (4) |
C121—P1—C131 | 103.65 (18) | C121—C122—H122 | 120.2 |
C111—P1—Pd1 | 107.63 (13) | C123—C122—H122 | 120.2 |
C121—P1—Pd1 | 117.41 (12) | C124—C123—C122 | 120.6 (4) |
C131—P1—Pd1 | 115.97 (13) | C124—C123—H123 | 119.7 |
C2—C1—C6 | 119.2 (4) | C122—C123—H123 | 119.7 |
C2—C1—Se1 | 118.9 (3) | C123—C124—C125 | 120.5 (4) |
C6—C1—Se1 | 121.8 (3) | C123—C124—H124 | 119.8 |
C1—C2—C3 | 119.6 (4) | C125—C124—H124 | 119.8 |
C1—C2—H2 | 120.2 | C124—C125—C126 | 119.8 (4) |
C3—C2—H2 | 120.2 | C124—C125—H125 | 120.1 |
C4—C3—C2 | 120.5 (4) | C126—C125—H125 | 120.1 |
C4—C3—H3 | 119.7 | C125—C126—C121 | 120.0 (4) |
C2—C3—H3 | 119.7 | C125—C126—H126 | 120.0 |
C5—C4—C3 | 120.3 (4) | C121—C126—H126 | 120.0 |
C5—C4—H4 | 119.8 | C136—C131—C132 | 119.0 (4) |
C3—C4—H4 | 119.8 | C136—C131—P1 | 120.7 (3) |
C4—C5—C6 | 119.8 (4) | C132—C131—P1 | 120.3 (3) |
C4—C5—H5 | 120.1 | C133—C132—C131 | 119.7 (4) |
C6—C5—H5 | 120.1 | C133—C132—H132 | 120.2 |
C5—C6—C1 | 120.4 (4) | C131—C132—H132 | 120.2 |
C5—C6—H6 | 119.8 | C134—C133—C132 | 120.5 (5) |
C1—C6—H6 | 119.8 | C134—C133—H133 | 119.7 |
C116—C111—C112 | 119.5 (4) | C132—C133—H133 | 119.7 |
C116—C111—P1 | 117.9 (3) | C135—C134—C133 | 120.3 (4) |
C112—C111—P1 | 122.4 (3) | C135—C134—H134 | 119.8 |
C113—C112—C111 | 120.5 (5) | C133—C134—H134 | 119.8 |
C113—C112—H112 | 119.8 | C134—C135—C136 | 120.4 (4) |
C111—C112—H112 | 119.8 | C134—C135—H135 | 119.8 |
C112—C113—C114 | 119.4 (5) | C136—C135—H135 | 119.8 |
C112—C113—H113 | 120.3 | C131—C136—C135 | 120.1 (4) |
C114—C113—H113 | 120.3 | C131—C136—H136 | 119.9 |
C113—C114—C115 | 121.3 (5) | C135—C136—H136 | 119.9 |
C113—C114—H114 | 119.3 | ||
P1—Pd1—Se1—C1 | −75.90 (12) | C112—C113—C114—C115 | −2.1 (9) |
Cl1—Pd1—Se1—C1 | 55.86 (18) | C113—C114—C115—C116 | 2.8 (8) |
Se1i—Pd1—Se1—C1 | 102.79 (12) | C114—C115—C116—C111 | −1.5 (7) |
P1—Pd1—Se1—Pd1i | −178.69 (3) | C112—C111—C116—C115 | −0.3 (6) |
Cl1—Pd1—Se1—Pd1i | −46.93 (14) | P1—C111—C116—C115 | 175.5 (3) |
Se1i—Pd1—Se1—Pd1i | 0.0 | C111—P1—C121—C122 | 2.9 (4) |
Cl1—Pd1—P1—C111 | −53.10 (14) | C131—P1—C121—C122 | −107.8 (3) |
Se1—Pd1—P1—C111 | 117.74 (13) | Pd1—P1—C121—C122 | 122.9 (3) |
Cl1—Pd1—P1—C121 | −172.11 (14) | C111—P1—C121—C126 | −177.7 (3) |
Se1—Pd1—P1—C121 | −1.27 (14) | C131—P1—C121—C126 | 71.7 (3) |
Cl1—Pd1—P1—C131 | 64.64 (14) | Pd1—P1—C121—C126 | −57.6 (3) |
Se1—Pd1—P1—C131 | −124.53 (14) | C126—C121—C122—C123 | 1.8 (6) |
Pd1—Se1—C1—C2 | 117.4 (3) | P1—C121—C122—C123 | −178.7 (3) |
Pd1i—Se1—C1—C2 | −144.5 (3) | C121—C122—C123—C124 | −1.5 (7) |
Pd1—Se1—C1—C6 | −59.1 (3) | C122—C123—C124—C125 | 0.2 (7) |
Pd1i—Se1—C1—C6 | 39.0 (3) | C123—C124—C125—C126 | 0.6 (7) |
C6—C1—C2—C3 | 2.2 (6) | C124—C125—C126—C121 | −0.1 (6) |
Se1—C1—C2—C3 | −174.4 (3) | C122—C121—C126—C125 | −1.1 (6) |
C1—C2—C3—C4 | −1.4 (6) | P1—C121—C126—C125 | 179.5 (3) |
C2—C3—C4—C5 | −0.4 (7) | C111—P1—C131—C136 | 82.5 (4) |
C3—C4—C5—C6 | 1.5 (7) | C121—P1—C131—C136 | −166.6 (3) |
C4—C5—C6—C1 | −0.8 (6) | Pd1—P1—C131—C136 | −36.4 (4) |
C2—C1—C6—C5 | −1.1 (6) | C111—P1—C131—C132 | −96.9 (4) |
Se1—C1—C6—C5 | 175.4 (3) | C121—P1—C131—C132 | 13.9 (4) |
C121—P1—C111—C116 | 72.8 (3) | Pd1—P1—C131—C132 | 144.1 (3) |
C131—P1—C111—C116 | −177.8 (3) | C136—C131—C132—C133 | −0.2 (6) |
Pd1—P1—C111—C116 | −53.5 (3) | P1—C131—C132—C133 | 179.3 (4) |
C121—P1—C111—C112 | −111.6 (4) | C131—C132—C133—C134 | −0.4 (7) |
C131—P1—C111—C112 | −2.2 (4) | C132—C133—C134—C135 | 0.1 (7) |
Pd1—P1—C111—C112 | 122.2 (3) | C133—C134—C135—C136 | 0.6 (7) |
C116—C111—C112—C113 | 1.0 (6) | C132—C131—C136—C135 | 0.9 (6) |
P1—C111—C112—C113 | −174.6 (4) | P1—C131—C136—C135 | −178.6 (3) |
C111—C112—C113—C114 | 0.2 (8) | C134—C135—C136—C131 | −1.2 (7) |
Symmetry code: (i) −x+1, −y+1, −z. |
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