trans-Dichloro­bis(tri-m-tolyl­phosphine)palladium(II)

Meijboom, R.; Muller, A.; Roodt, A.

doi:10.1107/S1600536806022264

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trans-Dichlorobis(tri-m-tolylphosphine)palladium(II)

R. Meijboom, A. Muller and A. Roodt

In the title compound, trans-[PdCl₂{P(C₇H₇)₃}₂], where P(C₇H₇)₃ is tri-m-tolylphosphine, the Pd atom is on an inversion centre, resulting in a trans-square-planar geometry. Selected geometric parameters are Pd—P and Pd—Cl distances of 2.3289 (4) and 2.2897 (4) Å, respectively, and a P—Pd—Cl angle of 87.77 (2)°. The effective cone angle for the tri-m-tolylphosphine is calculated to be 165°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022264/er2006sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022264/er2006Isup2.hkl Contains datablock I

CCDC reference: 613671

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.027
wR factor = 0.069
Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.66
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    -   C19     ..       6.09 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pd     -   Cl      ..       5.38 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   3 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: 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).

trans-Dichlorobis(tri-m-tolylphosphine)palladium(II) top

Crystal data top

[PdCl₂(C₂₁H₂₁P)₂]	Z = 1
M_r = 786	F(000) = 404
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.032
ω and φ scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→13
T_min = 0.858, T_max = 0.909	k = −13→13
44847 measured reflections	l = −14→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0319P)² + 1.0272P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.069	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 1.33 e Å⁻³
4673 reflections	Δρ_min = −0.50 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Comparative geometric parameters (Å) for selected trans-[PdCl₂(L)₂] complexes (L is a tertiary phosphine ligand) top

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).

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