trans-Dichloro­bis(triphenyl­phosphine)palladium(II) dichloro­ethane solvate

Steyl, G.

doi:10.1107/S1600536806017521

trans-Dichlorobis(triphenylphosphine)palladium(II) dichloroethane solvate

In the title compound, [PdCl₂(C₁₈H₁₅P)₂]·C₂H₄Cl₂, the Pd-complex and dichloroethane solvent molecule both possess a crystallographicaly imposed centre of symmetry. A square planar geometry about the palladium(II) metal centre is observed, while the trans triphenylphosphine ligands are in an eclipsed conformation. The most important bond distances include Pd-P 2.3394 (13) Å and Pd-Cl 2.3255 (12) Å. No hydrogen bonding is observed in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017521/cv2048sup1.cif Contains datablocks I, pdtr
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017521/cv2048Isup2.hkl Contains datablock I

CCDC reference: 610745

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R factor = 0.039
wR factor = 0.098
Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.13
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C41    -   C41_b  ...       1.38 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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: 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.

trans-Dichlorobis(triphenylphosphine)palladium(II) dichloroethane solvate top

Crystal data top

C₃₆H₃₀Cl₂P₂Pd·C₂H₄Cl₂	Z = 1
M_r = 800.81	F(000) = 406
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3774 independent reflections
Radiation source: fine-focus sealed tube	3487 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 512 pixels mm^-1	θ_max = 27.0°, θ_min = 2.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −12→12
T_min = 0.847, T_max = 0.905	l = −14→14
23018 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0356P)² + 3.9311P] where P = (F_o² + 2F_c²)/3
3774 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 2.99 e Å⁻³
0 restraints	Δρ_min = −1.41 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

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trans-Dichloro­bis(triphenyl­phosphine)palladium(II) dichloro­ethane solvate

Supporting information

Key indicators

checkCIF/PLATON results

trans-Dichlorobis(triphenylphosphine)palladium(II) dichloroethane solvate