Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022264/er2006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022264/er2006Isup2.hkl |
CCDC reference: 613671
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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
[PdCl2(C21H21P)2] | Z = 1 |
Mr = 786 | F(000) = 404 |
Triclinic, P1 | Dx = 1.391 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1864 (3) Å | Cell parameters from 7240 reflections |
b = 10.4434 (3) Å | θ = 2.3–28.3° |
c = 11.1137 (5) Å | µ = 0.75 mm−1 |
α = 108.102 (2)° | T = 100 K |
β = 114.206 (2)° | Cuboid, yellow |
γ = 102.811 (2)° | 0.21 × 0.15 × 0.13 mm |
V = 938.17 (7) Å3 |
Bruker X8 APEX-II 4K KappaCCD area-detector diffractometer | 4673 independent reflections |
Graphite monochromator | 4360 reflections with I > 2σ(I) |
Detector resolution: 8.2 pixels mm-1 | Rint = 0.032 |
ω and φ scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −13→13 |
Tmin = 0.858, Tmax = 0.909 | k = −13→13 |
44847 measured reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0319P)2 + 1.0272P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.069 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 1.33 e Å−3 |
4673 reflections | Δρmin = −0.50 e Å−3 |
217 parameters |
Experimental. The intensity data were collected on a Bruker X8 APEXII 4 K KappaCCD diffractometer using an exposure time of 10 s/frame. A total of 4504 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 99.6% completeness accomplished. Spectroscopic analysis: 1H NMR (CDCl3, 600 MHz, δ, p.p.m.): 7.57 (s, 6H, Ar), 7.44 (s, 6H, Ar), 7.21 (m, 6H, Ar), 7.12–7.03 (m, 6H, Ar), 2.33 (s, 18H, CH3); 13C{H} NMR (CDCl3, 75.45 MHz, δ, p.p.m.): 137.9, 136.2, 132.6, 131.7, 130.1, 128.2, 22.0; 31P{H} NMR (CDCl3, 121.46 MHz, δ, p.p.m.): 24.64. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8517 (2) | 0.49478 (19) | 0.71106 (19) | 0.0177 (3) | |
C2 | 0.9068 (2) | 0.59641 (19) | 0.66733 (19) | 0.0187 (3) | |
H2 | 0.8443 | 0.646 | 0.6311 | 0.022* | |
C3 | 1.0516 (2) | 0.6264 (2) | 0.6758 (2) | 0.0201 (3) | |
C4 | 1.1112 (2) | 0.7389 (2) | 0.6323 (2) | 0.0258 (4) | |
H4A | 1.0238 | 0.7591 | 0.5729 | 0.039* | |
H4B | 1.1568 | 0.7009 | 0.5741 | 0.039* | |
H4C | 1.1917 | 0.8299 | 0.7214 | 0.039* | |
C5 | 1.1400 (2) | 0.5501 (2) | 0.7274 (2) | 0.0240 (4) | |
H5 | 1.2385 | 0.5681 | 0.7332 | 0.029* | |
C6 | 1.0862 (2) | 0.4488 (2) | 0.7702 (2) | 0.0266 (4) | |
H6 | 1.1479 | 0.3979 | 0.8048 | 0.032* | |
C7 | 0.9419 (2) | 0.4208 (2) | 0.7628 (2) | 0.0235 (4) | |
H7 | 0.9057 | 0.3517 | 0.793 | 0.028* | |
C8 | 0.7177 (2) | 0.6107 (2) | 0.8804 (2) | 0.0195 (3) | |
C9 | 0.8601 (2) | 0.7336 (2) | 0.9697 (2) | 0.0221 (4) | |
H9 | 0.9372 | 0.7409 | 0.942 | 0.027* | |
C10 | 0.8923 (3) | 0.8465 (2) | 1.0992 (2) | 0.0270 (4) | |
C11 | 1.0461 (3) | 0.9804 (3) | 1.1916 (3) | 0.0387 (5) | |
H11A | 1.0427 | 1.0453 | 1.1439 | 0.058* | |
H11B | 1.1324 | 0.9495 | 1.2008 | 0.058* | |
H11C | 1.063 | 1.0333 | 1.2901 | 0.058* | |
C12 | 0.7780 (3) | 0.8328 (2) | 1.1379 (2) | 0.0297 (4) | |
H12 | 0.7976 | 0.9081 | 1.2256 | 0.036* | |
C13 | 0.6356 (3) | 0.7108 (2) | 1.0502 (2) | 0.0288 (4) | |
H13 | 0.559 | 0.7033 | 1.0785 | 0.035* | |
C14 | 0.6046 (2) | 0.6001 (2) | 0.9220 (2) | 0.0248 (4) | |
H14 | 0.5068 | 0.517 | 0.8622 | 0.03* | |
C15 | 0.5833 (2) | 0.2980 (2) | 0.6984 (2) | 0.0228 (4) | |
C16 | 0.6561 (2) | 0.2717 (2) | 0.8199 (2) | 0.0262 (4) | |
H16 | 0.7495 | 0.347 | 0.9073 | 0.031* | |
C17 | 0.5911 (3) | 0.1336 (2) | 0.8133 (3) | 0.0302 (4) | |
C18 | 0.6666 (3) | 0.1041 (3) | 0.9433 (3) | 0.0356 (5) | |
H18A | 0.6123 | 0.1171 | 0.9985 | 0.053* | |
H18B | 0.7773 | 0.1729 | 1.0079 | 0.053* | |
H18C | 0.6595 | 0.0029 | 0.9086 | 0.053* | |
C19 | 0.4539 (3) | 0.0271 (2) | 0.6861 (3) | 0.0324 (5) | |
H19 | 0.41 | −0.0661 | 0.6811 | 0.039* | |
C20 | 0.3795 (3) | 0.0519 (2) | 0.5673 (3) | 0.0343 (5) | |
H20 | 0.2842 | −0.0229 | 0.4815 | 0.041* | |
C21 | 0.4441 (2) | 0.1878 (2) | 0.5722 (3) | 0.0287 (4) | |
H21 | 0.3931 | 0.2051 | 0.4894 | 0.034* | |
P | 0.66511 (5) | 0.47356 (5) | 0.70156 (5) | 0.01677 (9) | |
Cl | 0.53757 (5) | 0.31954 (5) | 0.35465 (5) | 0.02334 (10) | |
Pd | 0.5 | 0.5 | 0.5 | 0.01543 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0170 (8) | 0.0211 (8) | 0.0210 (8) | 0.0101 (6) | 0.0128 (7) | 0.0106 (7) |
C2 | 0.0182 (8) | 0.0193 (8) | 0.0228 (8) | 0.0095 (6) | 0.0128 (7) | 0.0100 (7) |
C3 | 0.0196 (8) | 0.0191 (8) | 0.0217 (8) | 0.0066 (7) | 0.0131 (7) | 0.0069 (7) |
C4 | 0.0258 (9) | 0.0230 (9) | 0.0367 (10) | 0.0091 (7) | 0.0225 (8) | 0.0145 (8) |
C5 | 0.0180 (8) | 0.0303 (10) | 0.0275 (9) | 0.0116 (7) | 0.0144 (7) | 0.0123 (8) |
C6 | 0.0241 (9) | 0.0368 (11) | 0.0331 (10) | 0.0209 (8) | 0.0177 (8) | 0.0220 (9) |
C7 | 0.0242 (9) | 0.0308 (10) | 0.0302 (9) | 0.0171 (8) | 0.0182 (8) | 0.0206 (8) |
C8 | 0.0233 (8) | 0.0231 (8) | 0.0242 (8) | 0.0152 (7) | 0.0162 (7) | 0.0152 (7) |
C9 | 0.0255 (9) | 0.0255 (9) | 0.0253 (9) | 0.0142 (7) | 0.0173 (8) | 0.0144 (7) |
C10 | 0.0348 (10) | 0.0269 (10) | 0.0264 (9) | 0.0161 (8) | 0.0178 (8) | 0.0150 (8) |
C11 | 0.0443 (13) | 0.0316 (11) | 0.0307 (11) | 0.0089 (10) | 0.0199 (10) | 0.0070 (9) |
C12 | 0.0473 (12) | 0.0302 (10) | 0.0316 (10) | 0.0263 (9) | 0.0284 (10) | 0.0185 (9) |
C13 | 0.0397 (11) | 0.0364 (11) | 0.0399 (11) | 0.0278 (9) | 0.0323 (10) | 0.0259 (9) |
C14 | 0.0268 (9) | 0.0298 (10) | 0.0348 (10) | 0.0179 (8) | 0.0224 (8) | 0.0207 (8) |
C15 | 0.0278 (9) | 0.0222 (9) | 0.0387 (10) | 0.0165 (7) | 0.0260 (8) | 0.0204 (8) |
C16 | 0.0311 (10) | 0.0309 (10) | 0.0384 (11) | 0.0200 (8) | 0.0270 (9) | 0.0229 (9) |
C17 | 0.0425 (12) | 0.0387 (11) | 0.0485 (12) | 0.0308 (10) | 0.0391 (11) | 0.0326 (10) |
C18 | 0.0416 (12) | 0.0347 (11) | 0.0404 (12) | 0.0166 (10) | 0.0242 (10) | 0.0234 (10) |
C19 | 0.0386 (11) | 0.0239 (10) | 0.0547 (14) | 0.0167 (9) | 0.0358 (11) | 0.0215 (10) |
C20 | 0.0356 (11) | 0.0226 (10) | 0.0486 (13) | 0.0088 (8) | 0.0266 (10) | 0.0158 (9) |
C21 | 0.0306 (10) | 0.0224 (9) | 0.0430 (12) | 0.0116 (8) | 0.0247 (9) | 0.0175 (9) |
P | 0.0170 (2) | 0.0181 (2) | 0.0246 (2) | 0.01032 (17) | 0.01422 (18) | 0.01325 (18) |
Cl | 0.0271 (2) | 0.0222 (2) | 0.0279 (2) | 0.01682 (17) | 0.01626 (18) | 0.01186 (17) |
Pd | 0.01466 (9) | 0.01439 (9) | 0.02344 (10) | 0.00853 (7) | 0.01209 (7) | 0.01063 (7) |
C1—C7 | 1.389 (2) | C12—C13 | 1.388 (3) |
C1—C2 | 1.399 (2) | C12—H12 | 0.95 |
C1—P | 1.8189 (17) | C13—C14 | 1.383 (3) |
C2—C3 | 1.394 (2) | C13—H13 | 0.95 |
C2—H2 | 0.95 | C14—H14 | 0.95 |
C3—C5 | 1.398 (3) | C15—C21 | 1.394 (3) |
C3—C4 | 1.503 (3) | C15—C16 | 1.395 (3) |
C4—H4A | 0.98 | C15—P | 1.8215 (18) |
C4—H4B | 0.98 | C16—C17 | 1.412 (3) |
C4—H4C | 0.98 | C16—H16 | 0.95 |
C5—C6 | 1.383 (3) | C17—C19 | 1.379 (3) |
C5—H5 | 0.95 | C17—C18 | 1.498 (3) |
C6—C7 | 1.396 (3) | C18—H18A | 0.98 |
C6—H6 | 0.95 | C18—H18B | 0.98 |
C7—H7 | 0.95 | C18—H18C | 0.98 |
C8—C9 | 1.392 (3) | C19—C20 | 1.366 (3) |
C8—C14 | 1.401 (2) | C19—H19 | 0.95 |
C8—P | 1.8188 (19) | C20—C21 | 1.400 (3) |
C9—C10 | 1.399 (3) | C20—H20 | 0.95 |
C9—H9 | 0.95 | C21—H21 | 0.95 |
C10—C12 | 1.392 (3) | P—Pd | 2.3289 (4) |
C10—C11 | 1.510 (3) | Cl—Pd | 2.2897 (4) |
C11—H11A | 0.98 | Pd—Cli | 2.2897 (4) |
C11—H11B | 0.98 | Pd—Pi | 2.3289 (4) |
C11—H11C | 0.98 | ||
C7—C1—C2 | 119.62 (16) | C14—C13—C12 | 120.40 (18) |
C7—C1—P | 124.01 (13) | C14—C13—H13 | 119.8 |
C2—C1—P | 116.33 (13) | C12—C13—H13 | 119.8 |
C3—C2—C1 | 121.42 (16) | C13—C14—C8 | 119.90 (19) |
C3—C2—H2 | 119.3 | C13—C14—H14 | 120 |
C1—C2—H2 | 119.3 | C8—C14—H14 | 120 |
C2—C3—C5 | 118.01 (17) | C21—C15—C16 | 119.33 (18) |
C2—C3—C4 | 120.80 (17) | C21—C15—P | 119.20 (15) |
C5—C3—C4 | 121.18 (16) | C16—C15—P | 121.47 (16) |
C3—C4—H4A | 109.5 | C15—C16—C17 | 120.2 (2) |
C3—C4—H4B | 109.5 | C15—C16—H16 | 119.9 |
H4A—C4—H4B | 109.5 | C17—C16—H16 | 119.9 |
C3—C4—H4C | 109.5 | C19—C17—C16 | 118.8 (2) |
H4A—C4—H4C | 109.5 | C19—C17—C18 | 120.28 (19) |
H4B—C4—H4C | 109.5 | C16—C17—C18 | 120.9 (2) |
C6—C5—C3 | 121.02 (17) | C17—C18—H18A | 109.5 |
C6—C5—H5 | 119.5 | C17—C18—H18B | 109.5 |
C3—C5—H5 | 119.5 | H18A—C18—H18B | 109.5 |
C5—C6—C7 | 120.51 (17) | C17—C18—H18C | 109.5 |
C5—C6—H6 | 119.7 | H18A—C18—H18C | 109.5 |
C7—C6—H6 | 119.7 | H18B—C18—H18C | 109.5 |
C1—C7—C6 | 119.41 (17) | C20—C19—C17 | 121.80 (19) |
C1—C7—H7 | 120.3 | C20—C19—H19 | 119.1 |
C6—C7—H7 | 120.3 | C17—C19—H19 | 119.1 |
C9—C8—C14 | 119.07 (17) | C19—C20—C21 | 119.7 (2) |
C9—C8—P | 121.93 (13) | C19—C20—H20 | 120.1 |
C14—C8—P | 118.65 (15) | C21—C20—H20 | 120.1 |
C8—C9—C10 | 121.49 (17) | C15—C21—C20 | 120.1 (2) |
C8—C9—H9 | 119.3 | C15—C21—H21 | 119.9 |
C10—C9—H9 | 119.3 | C20—C21—H21 | 119.9 |
C12—C10—C9 | 118.17 (19) | C8—P—C1 | 104.74 (8) |
C12—C10—C11 | 121.51 (19) | C8—P—C15 | 104.42 (9) |
C9—C10—C11 | 120.30 (19) | C1—P—C15 | 108.57 (8) |
C10—C11—H11A | 109.5 | C8—P—Pd | 114.66 (6) |
C10—C11—H11B | 109.5 | C1—P—Pd | 109.91 (6) |
H11A—C11—H11B | 109.5 | C15—P—Pd | 113.96 (7) |
C10—C11—H11C | 109.5 | Cli—Pd—Cl | 180 |
H11A—C11—H11C | 109.5 | Cli—Pd—Pi | 87.772 (16) |
H11B—C11—H11C | 109.5 | Cl—Pd—Pi | 92.228 (16) |
C13—C12—C10 | 120.97 (19) | Cli—Pd—P | 92.228 (16) |
C13—C12—H12 | 119.5 | Cl—Pd—P | 87.772 (16) |
C10—C12—H12 | 119.5 | Pi—Pd—P | 180 |
C7—C1—C2—C3 | −0.6 (3) | C16—C15—C21—C20 | −0.7 (3) |
P—C1—C2—C3 | 177.28 (14) | P—C15—C21—C20 | 179.78 (16) |
C1—C2—C3—C5 | 1.0 (3) | C19—C20—C21—C15 | −0.5 (3) |
C1—C2—C3—C4 | −178.33 (17) | C9—C8—P—C1 | 21.84 (17) |
C2—C3—C5—C6 | −0.6 (3) | C14—C8—P—C1 | −165.00 (14) |
C4—C3—C5—C6 | 178.70 (19) | C9—C8—P—C15 | 135.89 (15) |
C3—C5—C6—C7 | −0.1 (3) | C14—C8—P—C15 | −50.95 (16) |
C2—C1—C7—C6 | −0.1 (3) | C9—C8—P—Pd | −98.70 (15) |
P—C1—C7—C6 | −177.85 (15) | C14—C8—P—Pd | 74.46 (15) |
C5—C6—C7—C1 | 0.5 (3) | C7—C1—P—C8 | 89.03 (17) |
C14—C8—C9—C10 | −0.3 (3) | C2—C1—P—C8 | −88.75 (15) |
P—C8—C9—C10 | 172.86 (14) | C7—C1—P—C15 | −22.07 (19) |
C8—C9—C10—C12 | 0.4 (3) | C2—C1—P—C15 | 160.15 (14) |
C8—C9—C10—C11 | −178.33 (19) | C7—C1—P—Pd | −147.33 (15) |
C9—C10—C12—C13 | −0.2 (3) | C2—C1—P—Pd | 34.89 (15) |
C11—C10—C12—C13 | 178.5 (2) | C21—C15—P—C8 | 134.50 (15) |
C10—C12—C13—C14 | −0.1 (3) | C16—C15—P—C8 | −44.97 (17) |
C12—C13—C14—C8 | 0.3 (3) | C21—C15—P—C1 | −114.19 (16) |
C9—C8—C14—C13 | −0.1 (3) | C16—C15—P—C1 | 66.34 (17) |
P—C8—C14—C13 | −173.43 (15) | C21—C15—P—Pd | 8.65 (17) |
C21—C15—C16—C17 | 1.5 (3) | C16—C15—P—Pd | −170.82 (13) |
P—C15—C16—C17 | −178.99 (14) | C8—P—Pd—Cli | −7.92 (7) |
C15—C16—C17—C19 | −1.1 (3) | C1—P—Pd—Cli | −125.56 (6) |
C15—C16—C17—C18 | −179.27 (18) | C15—P—Pd—Cli | 112.34 (6) |
C16—C17—C19—C20 | −0.2 (3) | C8—P—Pd—Cl | 172.08 (7) |
C18—C17—C19—C20 | 178.0 (2) | C1—P—Pd—Cl | 54.44 (6) |
C17—C19—C20—C21 | 1.0 (3) | C15—P—Pd—Cl | −67.66 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···Clii | 0.95 | 2.76 | 3.531 (2) | 139 |
C21—H21···Cl | 0.95 | 2.82 | 3.467 (2) | 126 |
Symmetry code: (ii) −x+1, −y, −z+1. |
L | Pd—P (Å) | Pd—Cl (Å) | Reference |
PPh3 | 2.337 (1) | 2.290 (1) | (a) |
PPh3 | 2.345 (1) | 2.296 (1) | (b) |
2.353 (1) | 2.281 (1) | ||
P(m-tol)3 | 2.3289 (4) | 2.2897 (4) | (c) |
PCy3 | 2.3628 (9) | 2.3012 (9) | (d) |
PPh(tBu)2 | 2.398 (2) | 2.301 (2) | (e) |
PPh2Cy | 2.3257 (9) | 2.2995 (9) | (f) |
PPh2[p-(tBuNO)Ph] | 2.3298 (6) | 2.2865 (7) | (g) |
PPh2CHCO2H | 2.326 (1) | 2.305 (1) | (h) |
PPh2(NC5H10) | 2.324 (2) | 2.289 (2) | (i) |
Notes: Cy is cyclohexyl; (a) Ferguson et al. (1982); (b) Kitano et al. (1983); (c) this work; (d) Grushin et al. (1994); (e) DiMeglio et al. (1990); (f) Meij et al. (2003); (g) Leznoff et al. (1999); (h) Edwards et al. (1998); (i) Burrow et al. (1994). |