Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017521/cv2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017521/cv2048Isup2.hkl |
CCDC reference: 610745
Data collection: Apex2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXL97.
C36H30Cl2P2Pd·C2H4Cl2 | Z = 1 |
Mr = 800.81 | F(000) = 406 |
Triclinic, P1 | Dx = 1.535 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.208 (5) Å | Cell parameters from 5514 reflections |
b = 9.481 (5) Å | θ = 2.4–28.4° |
c = 11.599 (5) Å | µ = 0.96 mm−1 |
α = 110.177 (5)° | T = 100 K |
β = 107.723 (5)° | Block, yellow |
γ = 98.921 (5)° | 0.17 × 0.15 × 0.10 mm |
V = 866.2 (8) Å3 |
Bruker SMART CCD area-detector diffractometer | 3774 independent reflections |
Radiation source: fine-focus sealed tube | 3487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 512 pixels mm-1 | θmax = 27.0°, θmin = 2.4° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −12→12 |
Tmin = 0.847, Tmax = 0.905 | l = −14→14 |
23018 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0356P)2 + 3.9311P] where P = (Fo2 + 2Fc2)/3 |
3774 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 2.99 e Å−3 |
0 restraints | Δρmin = −1.41 e Å−3 |
Experimental. 1H NMR (CDCl3, 300 MHz): δ 7.68 (m, 12), 7.45 (t, 6), 7.35 (m, 12); 31P (CDCl3, 121.497 MHz): δ 24.52 (s). |
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 | ||
Pd | 0.5000 | 0.5000 | 0.5000 | 0.01059 (10) | |
P | 0.50557 (9) | 0.51019 (9) | 0.70576 (8) | 0.01194 (17) | |
Cl | 0.28594 (8) | 0.27371 (8) | 0.39862 (7) | 0.01059 (10) | |
Cl41 | 0.94849 (12) | 0.21404 (12) | 0.59622 (9) | 0.0304 (2) | |
C32 | 0.7823 (4) | 0.5724 (4) | 0.9282 (3) | 0.0180 (7) | |
H32 | 0.7607 | 0.4641 | 0.8996 | 0.022* | |
C36 | 0.7166 (4) | 0.7976 (4) | 0.9004 (3) | 0.0194 (7) | |
H36 | 0.6505 | 0.8408 | 0.8534 | 0.023* | |
C25 | 0.5670 (5) | 0.0835 (4) | 0.6662 (4) | 0.0251 (8) | |
H25 | 0.6296 | 0.0248 | 0.6346 | 0.030* | |
C14 | 0.0974 (4) | 0.6867 (4) | 0.7977 (3) | 0.0188 (7) | |
H14 | 0.0119 | 0.7170 | 0.8144 | 0.023* | |
C26 | 0.5739 (4) | 0.2284 (4) | 0.6612 (3) | 0.0209 (7) | |
H26 | 0.6400 | 0.2658 | 0.6249 | 0.025* | |
C31 | 0.6822 (4) | 0.6344 (4) | 0.8555 (3) | 0.0143 (6) | |
C21 | 0.4820 (4) | 0.3184 (4) | 0.7106 (3) | 0.0142 (6) | |
C34 | 0.9488 (4) | 0.8328 (4) | 1.0866 (3) | 0.0221 (7) | |
H34 | 1.0377 | 0.8988 | 1.1630 | 0.026* | |
C11 | 0.3476 (4) | 0.5844 (4) | 0.7444 (3) | 0.0139 (6) | |
C35 | 0.8491 (4) | 0.8953 (4) | 1.0149 (4) | 0.0226 (7) | |
H35 | 0.8714 | 1.0036 | 1.0439 | 0.027* | |
C23 | 0.3755 (4) | 0.1148 (4) | 0.7676 (4) | 0.0240 (7) | |
H23 | 0.3090 | 0.0764 | 0.8031 | 0.029* | |
C24 | 0.4672 (5) | 0.0261 (4) | 0.7182 (4) | 0.0261 (8) | |
H24 | 0.4614 | −0.0718 | 0.7200 | 0.031* | |
C13 | 0.1007 (4) | 0.6467 (4) | 0.6720 (3) | 0.0190 (7) | |
H13 | 0.0193 | 0.6541 | 0.6055 | 0.023* | |
C15 | 0.2225 (4) | 0.6815 (4) | 0.8989 (3) | 0.0207 (7) | |
H15 | 0.2226 | 0.7123 | 0.9842 | 0.025* | |
C12 | 0.2250 (4) | 0.5954 (4) | 0.6447 (3) | 0.0160 (6) | |
H12 | 0.2263 | 0.5684 | 0.5601 | 0.019* | |
C16 | 0.3470 (4) | 0.6303 (4) | 0.8722 (3) | 0.0186 (7) | |
H16 | 0.4302 | 0.6266 | 0.9398 | 0.022* | |
C33 | 0.9148 (4) | 0.6718 (4) | 1.0436 (3) | 0.0211 (7) | |
H33 | 0.9806 | 0.6295 | 1.0918 | 0.025* | |
C22 | 0.3828 (4) | 0.2616 (4) | 0.7641 (3) | 0.0187 (7) | |
H22 | 0.3216 | 0.3210 | 0.7974 | 0.022* | |
C41 | 0.9615 (7) | 0.0049 (9) | 0.5432 (5) | 0.073 (2) | |
H41A | 1.0226 | −0.0124 | 0.6188 | 0.087* | |
H41B | 0.8564 | −0.0705 | 0.4987 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd | 0.01057 (16) | 0.01219 (16) | 0.01081 (15) | 0.00430 (11) | 0.00509 (11) | 0.00557 (12) |
P | 0.0125 (4) | 0.0134 (4) | 0.0117 (4) | 0.0055 (3) | 0.0055 (3) | 0.0058 (3) |
Cl | 0.01057 (16) | 0.01219 (16) | 0.01081 (15) | 0.00430 (11) | 0.00509 (11) | 0.00557 (12) |
Cl41 | 0.0341 (5) | 0.0332 (5) | 0.0262 (5) | 0.0114 (4) | 0.0130 (4) | 0.0132 (4) |
C32 | 0.0187 (16) | 0.0203 (16) | 0.0169 (16) | 0.0072 (13) | 0.0079 (13) | 0.0082 (13) |
C36 | 0.0214 (17) | 0.0188 (16) | 0.0196 (16) | 0.0073 (13) | 0.0077 (14) | 0.0093 (13) |
C25 | 0.032 (2) | 0.0214 (18) | 0.0219 (17) | 0.0157 (15) | 0.0074 (15) | 0.0078 (14) |
C14 | 0.0166 (16) | 0.0172 (16) | 0.0235 (17) | 0.0072 (13) | 0.0103 (14) | 0.0063 (13) |
C26 | 0.0231 (17) | 0.0213 (17) | 0.0202 (17) | 0.0093 (14) | 0.0088 (14) | 0.0091 (14) |
C31 | 0.0136 (14) | 0.0172 (15) | 0.0126 (14) | 0.0046 (12) | 0.0063 (12) | 0.0055 (12) |
C21 | 0.0165 (15) | 0.0141 (15) | 0.0106 (14) | 0.0061 (12) | 0.0028 (12) | 0.0050 (12) |
C34 | 0.0160 (16) | 0.0284 (19) | 0.0151 (16) | 0.0005 (14) | 0.0054 (13) | 0.0045 (14) |
C11 | 0.0140 (15) | 0.0133 (14) | 0.0162 (15) | 0.0058 (12) | 0.0079 (12) | 0.0056 (12) |
C35 | 0.0253 (18) | 0.0170 (16) | 0.0207 (17) | 0.0025 (14) | 0.0084 (14) | 0.0045 (14) |
C23 | 0.0228 (18) | 0.0253 (18) | 0.0233 (18) | 0.0018 (14) | 0.0044 (14) | 0.0158 (15) |
C24 | 0.030 (2) | 0.0167 (17) | 0.0235 (18) | 0.0058 (14) | −0.0014 (15) | 0.0102 (14) |
C13 | 0.0168 (16) | 0.0199 (16) | 0.0191 (16) | 0.0081 (13) | 0.0049 (13) | 0.0073 (13) |
C15 | 0.0250 (18) | 0.0255 (18) | 0.0172 (16) | 0.0113 (14) | 0.0129 (14) | 0.0094 (14) |
C12 | 0.0164 (15) | 0.0175 (15) | 0.0140 (15) | 0.0061 (12) | 0.0055 (12) | 0.0061 (12) |
C16 | 0.0202 (16) | 0.0224 (17) | 0.0159 (15) | 0.0103 (13) | 0.0076 (13) | 0.0089 (13) |
C33 | 0.0175 (16) | 0.0290 (19) | 0.0180 (16) | 0.0082 (14) | 0.0054 (13) | 0.0120 (14) |
C22 | 0.0172 (16) | 0.0208 (17) | 0.0171 (16) | 0.0050 (13) | 0.0043 (13) | 0.0087 (13) |
C41 | 0.039 (3) | 0.120 (6) | 0.043 (3) | −0.026 (3) | −0.003 (2) | 0.053 (4) |
Pd—Cli | 2.3255 (12) | C21—C22 | 1.390 (5) |
Pd—Cl | 2.3255 (12) | C34—C33 | 1.381 (5) |
Pd—Pi | 2.3394 (13) | C34—C35 | 1.389 (5) |
Pd—P | 2.3394 (13) | C34—H34 | 0.9300 |
P—C11 | 1.819 (3) | C11—C16 | 1.395 (5) |
P—C21 | 1.819 (3) | C11—C12 | 1.396 (4) |
P—C31 | 1.824 (3) | C35—H35 | 0.9300 |
Cl41—C41 | 1.898 (8) | C23—C24 | 1.389 (6) |
C32—C31 | 1.394 (5) | C23—C22 | 1.398 (5) |
C32—C33 | 1.396 (5) | C23—H23 | 0.9300 |
C32—H32 | 0.9300 | C24—H24 | 0.9300 |
C36—C35 | 1.387 (5) | C13—C12 | 1.390 (5) |
C36—C31 | 1.399 (5) | C13—H13 | 0.9300 |
C36—H36 | 0.9300 | C15—C16 | 1.390 (5) |
C25—C24 | 1.382 (6) | C15—H15 | 0.9300 |
C25—C26 | 1.388 (5) | C12—H12 | 0.9300 |
C25—H25 | 0.9300 | C16—H16 | 0.9300 |
C14—C13 | 1.385 (5) | C33—H33 | 0.9300 |
C14—C15 | 1.394 (5) | C22—H22 | 0.9300 |
C14—H14 | 0.9300 | C41—C41ii | 1.380 (12) |
C26—C21 | 1.399 (5) | C41—H41A | 0.9700 |
C26—H26 | 0.9300 | C41—H41B | 0.9700 |
Cli—Pd—Cl | 180.00 (4) | C16—C11—C12 | 119.5 (3) |
Cli—Pd—Pi | 88.03 (3) | C16—C11—P | 121.0 (2) |
Cl—Pd—Pi | 91.97 (3) | C12—C11—P | 119.5 (2) |
Cli—Pd—P | 91.97 (3) | C36—C35—C34 | 120.6 (3) |
Cl—Pd—P | 88.03 (3) | C36—C35—H35 | 119.7 |
Pi—Pd—P | 180.0 | C34—C35—H35 | 119.7 |
C11—P—C21 | 107.64 (15) | C24—C23—C22 | 120.2 (3) |
C11—P—C31 | 102.66 (15) | C24—C23—H23 | 119.9 |
C21—P—C31 | 102.99 (15) | C22—C23—H23 | 119.9 |
C11—P—Pd | 111.14 (11) | C25—C24—C23 | 120.0 (3) |
C21—P—Pd | 112.31 (10) | C25—C24—H24 | 120.0 |
C31—P—Pd | 119.08 (11) | C23—C24—H24 | 120.0 |
C31—C32—C33 | 120.4 (3) | C14—C13—C12 | 120.5 (3) |
C31—C32—H32 | 119.8 | C14—C13—H13 | 119.8 |
C33—C32—H32 | 119.8 | C12—C13—H13 | 119.8 |
C35—C36—C31 | 120.2 (3) | C16—C15—C14 | 119.9 (3) |
C35—C36—H36 | 119.9 | C16—C15—H15 | 120.0 |
C31—C36—H36 | 119.9 | C14—C15—H15 | 120.0 |
C24—C25—C26 | 120.2 (3) | C13—C12—C11 | 120.0 (3) |
C24—C25—H25 | 119.9 | C13—C12—H12 | 120.0 |
C26—C25—H25 | 119.9 | C11—C12—H12 | 120.0 |
C13—C14—C15 | 119.8 (3) | C15—C16—C11 | 120.3 (3) |
C13—C14—H14 | 120.1 | C15—C16—H16 | 119.9 |
C15—C14—H14 | 120.1 | C11—C16—H16 | 119.9 |
C25—C26—C21 | 120.2 (3) | C34—C33—C32 | 120.4 (3) |
C25—C26—H26 | 119.9 | C34—C33—H33 | 119.8 |
C21—C26—H26 | 119.9 | C32—C33—H33 | 119.8 |
C32—C31—C36 | 118.9 (3) | C21—C22—C23 | 119.7 (3) |
C32—C31—P | 122.2 (3) | C21—C22—H22 | 120.1 |
C36—C31—P | 118.8 (2) | C23—C22—H22 | 120.1 |
C22—C21—C26 | 119.6 (3) | C41ii—C41—Cl41 | 102.5 (6) |
C22—C21—P | 123.4 (3) | C41ii—C41—H41A | 111.3 |
C26—C21—P | 116.9 (3) | Cl41—C41—H41A | 111.3 |
C33—C34—C35 | 119.5 (3) | C41ii—C41—H41B | 111.3 |
C33—C34—H34 | 120.2 | Cl41—C41—H41B | 111.3 |
C35—C34—H34 | 120.2 | H41A—C41—H41B | 109.2 |
Cli—Pd—P—C11 | 102.80 (12) | Pd—P—C21—C26 | 46.5 (3) |
Cl—Pd—P—C11 | −77.20 (12) | C21—P—C11—C16 | 69.6 (3) |
Cli—Pd—P—C21 | −136.55 (12) | C31—P—C11—C16 | −38.6 (3) |
Cl—Pd—P—C21 | 43.45 (12) | Pd—P—C11—C16 | −167.0 (2) |
Cli—Pd—P—C31 | −16.14 (12) | C21—P—C11—C12 | −110.2 (3) |
Cl—Pd—P—C31 | 163.86 (12) | C31—P—C11—C12 | 141.5 (3) |
C24—C25—C26—C21 | 1.0 (5) | Pd—P—C11—C12 | 13.1 (3) |
C33—C32—C31—C36 | −0.2 (5) | C31—C36—C35—C34 | −0.3 (5) |
C33—C32—C31—P | −178.9 (3) | C33—C34—C35—C36 | −0.3 (5) |
C35—C36—C31—C32 | 0.5 (5) | C26—C25—C24—C23 | −1.1 (5) |
C35—C36—C31—P | 179.3 (3) | C22—C23—C24—C25 | 0.5 (5) |
C11—P—C31—C32 | 124.3 (3) | C15—C14—C13—C12 | 2.5 (5) |
C21—P—C31—C32 | 12.6 (3) | C13—C14—C15—C16 | −2.5 (5) |
Pd—P—C31—C32 | −112.5 (3) | C14—C13—C12—C11 | −0.2 (5) |
C11—P—C31—C36 | −54.4 (3) | C16—C11—C12—C13 | −2.2 (5) |
C21—P—C31—C36 | −166.1 (3) | P—C11—C12—C13 | 177.7 (3) |
Pd—P—C31—C36 | 68.8 (3) | C14—C15—C16—C11 | 0.2 (5) |
C25—C26—C21—C22 | −0.3 (5) | C12—C11—C16—C15 | 2.1 (5) |
C25—C26—C21—P | 177.5 (3) | P—C11—C16—C15 | −177.7 (3) |
C11—P—C21—C22 | −13.0 (3) | C35—C34—C33—C32 | 0.7 (5) |
C31—P—C21—C22 | 95.0 (3) | C31—C32—C33—C34 | −0.4 (5) |
Pd—P—C21—C22 | −135.7 (2) | C26—C21—C22—C23 | −0.3 (5) |
C11—P—C21—C26 | 169.2 (3) | P—C21—C22—C23 | −178.0 (3) |
C31—P—C21—C26 | −82.8 (3) | C24—C23—C22—C21 | 0.2 (5) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1. |