trans-Dichloro­bis[diphen­yl(p-tol­yl)­phos­phine]­palladium(II)

The centrosymmetric title compound, [PdCl₂(C₁₉H₁₇P)₂], crystallizes with a square-planar geometry about the Pd^II metal centre. The most important bond distances include Pd—P (trans P) of 2.3404 (9) Å and Pd—Cl (trans Cl) of 2.2977 (12) Å. Weak intra- and inter­molecular hydrogen bonding is observed in the solid-state structure between the chloro and phenyl H atoms. This weak inter­molecular hydrogen-bonding pattern forms a one-dimensional chain along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.022
• wR factor = 0.054
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pd     -   Cl      ..       5.69 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

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Computing details

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[diphenyl(p-tolyl)phosphine]palladium(II)

Crystal data

[PdCl2(C19H17P)2]	Z = 1
Mr = 729.89	F(000) = 372
Triclinic, P1	Dx = 1.489 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.960 (5) Å	Cell parameters from 9926 reflections
b = 9.985 (5) Å	θ = 2.4–28.3°
c = 10.255 (5) Å	µ = 0.86 mm^−1
α = 88.312 (5)°	T = 100 K
β = 68.129 (5)°	Cuboid, yellow
γ = 61.045 (5)°	0.26 × 0.16 × 0.11 mm
V = 813.7 (7) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3918 independent reflections
Radiation source: fine-focus sealed tube	3644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 512 pixels mm^-1	θmax = 28.0°, θmin = 2.4°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −13→13
Tmin = 0.847, Tmax = 0.905	l = −13→13
17732 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0193P)^2 + 0.5842P] where P = (Fo^2 + 2Fc^2)/3
3918 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. 1H NMR (CDCl3, 300 MHz): δ 7.72 (m, 4), 7.58 (m, 2), 7.37 (m, 6), 7.16 (d, 2); 13 C (CDCl3 75.476 MHz): 141.2 (s), 135.4 (m), 130.8 (s), 130.3 (t), 129.3 (t), 125.4 (t), 126.4 (t), 21.9 (s); 31P (CDCl3, 121.497 MHz): δ 23.97 (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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	0.4166 (2)	0.42900 (19)	0.31474 (16)	0.0159 (3)
C12	0.4737 (2)	0.3127 (2)	0.39196 (18)	0.0227 (4)
H12	0.4105	0.2669	0.4363	0.027*
C13	0.6250 (2)	0.2647 (2)	0.4030 (2)	0.0272 (4)
H13	0.6637	0.1852	0.4527	0.033*
C14	0.7184 (2)	0.3346 (2)	0.34036 (18)	0.0231 (4)
H14	0.8184	0.3035	0.3495	0.028*
C15	0.6621 (2)	0.4507 (2)	0.26429 (18)	0.0228 (4)
H15	0.7243	0.4980	0.2225	0.027*
C16	0.5129 (2)	0.4974 (2)	0.24985 (17)	0.0203 (3)
H16	0.4770	0.5742	0.1969	0.024*
C21	0.17295 (19)	0.67956 (18)	0.24008 (16)	0.0149 (3)
C22	0.1419 (2)	0.8024 (2)	0.33116 (17)	0.0186 (3)
H22	0.1409	0.7896	0.4216	0.022*
C23	0.1126 (2)	0.9429 (2)	0.28736 (18)	0.0215 (3)
H23	0.0929	1.0238	0.3481	0.026*
C24	0.1126 (2)	0.9631 (2)	0.15265 (19)	0.0226 (4)
H24	0.0919	1.0578	0.1238	0.027*
C25	0.1433 (2)	0.8426 (2)	0.06156 (18)	0.0201 (3)
H25	0.1434	0.8562	−0.0286	0.024*
C26	0.1739 (2)	0.70072 (19)	0.10493 (17)	0.0166 (3)
H26	0.1952	0.6197	0.0432	0.020*
C31	0.2611 (2)	0.36918 (18)	0.14740 (16)	0.0147 (3)
C32	0.4227 (2)	0.2625 (2)	0.05055 (17)	0.0185 (3)
H32	0.5150	0.2498	0.0645	0.022*
C33	0.4471 (2)	0.1741 (2)	−0.06768 (18)	0.0221 (3)
H33	0.5560	0.1018	−0.1312	0.026*
C34	0.3116 (2)	0.1920 (2)	−0.09249 (17)	0.0203 (3)
C35	0.1500 (2)	0.2987 (2)	0.00613 (18)	0.0211 (3)
H35	0.0576	0.3121	−0.0080	0.025*
C36	0.1249 (2)	0.38523 (19)	0.12513 (18)	0.0197 (3)
H36	0.0159	0.4546	0.1907	0.024*
C341	0.3374 (3)	0.0983 (3)	−0.2207 (2)	0.0343 (5)
H34A	0.2301	0.1264	−0.2197	0.051*	0.50
H34B	0.3972	−0.0106	−0.2180	0.051*	0.50
H34C	0.4013	0.1192	−0.3063	0.051*	0.50
H34D	0.4556	0.0302	−0.2763	0.051*	0.50
H34E	0.2886	0.1673	−0.2780	0.051*	0.50
H34F	0.2845	0.0375	−0.1896	0.051*	0.50
P	0.21720 (5)	0.49482 (5)	0.30016 (4)	0.01363 (9)
Cl	0.15888 (5)	0.23264 (5)	0.44985 (4)	0.02223 (9)
Pd	0.0000	0.5000	0.5000	0.01434 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0157 (7)	0.0175 (8)	0.0122 (7)	−0.0077 (6)	−0.0044 (6)	−0.0016 (6)
C12	0.0269 (9)	0.0233 (9)	0.0234 (8)	−0.0153 (8)	−0.0124 (7)	0.0063 (7)
C13	0.0303 (10)	0.0259 (9)	0.0296 (9)	−0.0128 (8)	−0.0186 (8)	0.0086 (7)
C14	0.0193 (8)	0.0272 (9)	0.0203 (8)	−0.0084 (7)	−0.0099 (7)	−0.0025 (7)
C15	0.0192 (8)	0.0289 (9)	0.0210 (8)	−0.0143 (7)	−0.0056 (7)	0.0005 (7)
C16	0.0191 (8)	0.0233 (9)	0.0178 (7)	−0.0109 (7)	−0.0068 (6)	0.0044 (6)
C21	0.0129 (7)	0.0162 (7)	0.0158 (7)	−0.0090 (6)	−0.0041 (6)	0.0028 (6)
C22	0.0183 (8)	0.0218 (8)	0.0150 (7)	−0.0120 (7)	−0.0035 (6)	0.0004 (6)
C23	0.0196 (8)	0.0179 (8)	0.0245 (8)	−0.0111 (7)	−0.0042 (7)	−0.0011 (6)
C24	0.0195 (8)	0.0181 (8)	0.0297 (9)	−0.0107 (7)	−0.0083 (7)	0.0074 (7)
C25	0.0185 (8)	0.0225 (9)	0.0217 (8)	−0.0112 (7)	−0.0098 (6)	0.0091 (6)
C26	0.0146 (7)	0.0190 (8)	0.0172 (7)	−0.0095 (6)	−0.0061 (6)	0.0020 (6)
C31	0.0167 (7)	0.0152 (7)	0.0135 (7)	−0.0097 (6)	−0.0051 (6)	0.0020 (6)
C32	0.0154 (8)	0.0222 (8)	0.0183 (7)	−0.0110 (7)	−0.0052 (6)	0.0006 (6)
C33	0.0188 (8)	0.0235 (9)	0.0183 (8)	−0.0103 (7)	−0.0024 (6)	−0.0032 (6)
C34	0.0269 (9)	0.0191 (8)	0.0187 (7)	−0.0140 (7)	−0.0099 (7)	0.0029 (6)
C35	0.0217 (8)	0.0224 (9)	0.0257 (8)	−0.0128 (7)	−0.0140 (7)	0.0045 (7)
C36	0.0151 (8)	0.0179 (8)	0.0230 (8)	−0.0071 (7)	−0.0063 (6)	−0.0001 (6)
C341	0.0391 (11)	0.0377 (11)	0.0268 (9)	−0.0199 (10)	−0.0128 (9)	−0.0050 (8)
P	0.01400 (19)	0.01434 (19)	0.01187 (17)	−0.00810 (16)	−0.00333 (15)	0.00109 (14)
Cl	0.0201 (2)	0.01468 (19)	0.02427 (19)	−0.00908 (16)	−0.00103 (15)	0.00074 (15)
Pd	0.01477 (9)	0.01359 (9)	0.01238 (8)	−0.00817 (7)	−0.00191 (6)	0.00071 (6)

Geometric parameters (Å, º)

C11—C12	1.393 (2)	C26—H26	0.9300
C11—C16	1.400 (2)	C31—C32	1.387 (2)
C11—P	1.8300 (19)	C31—C36	1.392 (2)
C12—C13	1.392 (3)	C31—P	1.8146 (17)
C12—H12	0.9300	C32—C33	1.394 (2)
C13—C14	1.386 (3)	C32—H32	0.9300
C13—H13	0.9300	C33—C34	1.392 (3)
C14—C15	1.382 (3)	C33—H33	0.9300
C14—H14	0.9300	C34—C35	1.392 (2)
C15—C16	1.392 (3)	C34—C341	1.503 (2)
C15—H15	0.9300	C35—C36	1.387 (2)
C16—H16	0.9300	C35—H35	0.9300
C21—C26	1.393 (2)	C36—H36	0.9300
C21—C22	1.399 (2)	C341—H34A	0.9600
C21—P	1.8233 (18)	C341—H34B	0.9600
C22—C23	1.385 (2)	C341—H34C	0.9600
C22—H22	0.9300	C341—H34D	0.9600
C23—C24	1.390 (3)	C341—H34E	0.9600
C23—H23	0.9300	C341—H34F	0.9600
C24—C25	1.382 (3)	P—Pd	2.3404 (9)
C24—H24	0.9300	Cl—Pd	2.2977 (12)
C25—C26	1.394 (2)	Pd—Cl^i	2.2977 (12)
C25—H25	0.9300	Pd—P^i	2.3404 (9)
C12—C11—C16	118.95 (16)	C32—C33—H33	119.4
C12—C11—P	120.96 (13)	C33—C34—C35	118.05 (15)
C16—C11—P	120.08 (13)	C33—C34—C341	121.44 (16)
C13—C12—C11	120.28 (17)	C35—C34—C341	120.51 (17)
C13—C12—H12	119.9	C36—C35—C34	120.96 (16)
C11—C12—H12	119.9	C36—C35—H35	119.5
C14—C13—C12	120.45 (17)	C34—C35—H35	119.5
C14—C13—H13	119.8	C35—C36—C31	120.61 (15)
C12—C13—H13	119.8	C35—C36—H36	119.7
C15—C14—C13	119.62 (17)	C31—C36—H36	119.7
C15—C14—H14	120.2	C34—C341—H34A	109.5
C13—C14—H14	120.2	C34—C341—H34B	109.5
C14—C15—C16	120.47 (17)	H34A—C341—H34B	109.5
C14—C15—H15	119.8	C34—C341—H34C	109.5
C16—C15—H15	119.8	H34A—C341—H34C	109.5
C15—C16—C11	120.21 (16)	H34B—C341—H34C	109.5
C15—C16—H16	119.9	C34—C341—H34D	109.5
C11—C16—H16	119.9	H34A—C341—H34D	141.1
C26—C21—C22	119.02 (15)	H34B—C341—H34D	56.3
C26—C21—P	122.08 (12)	H34C—C341—H34D	56.3
C22—C21—P	118.87 (13)	C34—C341—H34E	109.5
C23—C22—C21	120.39 (16)	H34A—C341—H34E	56.3
C23—C22—H22	119.8	H34B—C341—H34E	141.1
C21—C22—H22	119.8	H34C—C341—H34E	56.3
C22—C23—C24	120.08 (16)	H34D—C341—H34E	109.5
C22—C23—H23	120.0	C34—C341—H34F	109.5
C24—C23—H23	120.0	H34A—C341—H34F	56.3
C25—C24—C23	120.11 (16)	H34B—C341—H34F	56.3
C25—C24—H24	119.9	H34C—C341—H34F	141.1
C23—C24—H24	119.9	H34D—C341—H34F	109.5
C24—C25—C26	119.95 (16)	H34E—C341—H34F	109.5
C24—C25—H25	120.0	C31—P—C21	103.80 (8)
C26—C25—H25	120.0	C31—P—C11	107.44 (7)
C21—C26—C25	120.44 (15)	C21—P—C11	102.58 (7)
C21—C26—H26	119.8	C31—P—Pd	108.95 (6)
C25—C26—H26	119.8	C21—P—Pd	116.23 (5)
C32—C31—C36	118.98 (15)	C11—P—Pd	116.77 (6)
C32—C31—P	123.23 (13)	Cl—Pd—Cl^i	180.00 (2)
C36—C31—P	117.76 (12)	Cl—Pd—P^i	93.40 (2)
C31—C32—C33	120.11 (16)	Cl^i—Pd—P^i	86.60 (2)
C31—C32—H32	119.9	Cl—Pd—P	86.60 (2)
C33—C32—H32	119.9	Cl^i—Pd—P	93.40 (2)
C34—C33—C32	121.27 (15)	P^i—Pd—P	180.0
C34—C33—H33	119.4
C16—C11—C12—C13	−0.6 (2)	P—C31—C36—C35	176.51 (13)
P—C11—C12—C13	−179.50 (13)	C32—C31—P—C21	98.65 (15)
C11—C12—C13—C14	1.6 (3)	C36—C31—P—C21	−79.33 (14)
C12—C13—C14—C15	−1.2 (3)	C32—C31—P—C11	−9.54 (16)
C13—C14—C15—C16	−0.2 (3)	C36—C31—P—C11	172.48 (13)
C14—C15—C16—C11	1.2 (3)	C32—C31—P—Pd	−136.92 (13)
C12—C11—C16—C15	−0.8 (2)	C36—C31—P—Pd	45.11 (14)
P—C11—C16—C15	178.11 (12)	C26—C21—P—C31	1.38 (15)
C26—C21—C22—C23	0.0 (2)	C22—C21—P—C31	−176.72 (13)
P—C21—C22—C23	178.15 (13)	C26—C21—P—C11	113.16 (13)
C21—C22—C23—C24	0.5 (2)	C22—C21—P—C11	−64.94 (14)
C22—C23—C24—C25	−0.6 (3)	C26—C21—P—Pd	−118.20 (12)
C23—C24—C25—C26	0.1 (3)	C22—C21—P—Pd	63.70 (14)
C22—C21—C26—C25	−0.4 (2)	C12—C11—P—C31	−87.65 (15)
P—C21—C26—C25	−178.52 (12)	C16—C11—P—C31	93.43 (14)
C24—C25—C26—C21	0.4 (2)	C12—C11—P—C21	163.31 (13)
C36—C31—C32—C33	0.5 (2)	C16—C11—P—C21	−15.61 (14)
P—C31—C32—C33	−177.40 (13)	C12—C11—P—Pd	35.01 (15)
C31—C32—C33—C34	0.9 (3)	C16—C11—P—Pd	−143.91 (11)
C32—C33—C34—C35	−1.4 (3)	C31—P—Pd—Cl	52.89 (6)
C32—C33—C34—C341	179.28 (18)	C21—P—Pd—Cl	169.65 (6)
C33—C34—C35—C36	0.4 (3)	C11—P—Pd—Cl	−68.99 (6)
C341—C34—C35—C36	179.71 (17)	C31—P—Pd—Cl^i	−127.11 (6)
C34—C35—C36—C31	1.1 (3)	C21—P—Pd—Cl^i	−10.35 (6)
C32—C31—C36—C35	−1.6 (3)	C11—P—Pd—Cl^i	111.01 (6)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl	0.93	2.64	3.440 (2)	144
C23—H23···Cl^ii	0.93	2.80	3.675 (2)	157

Symmetry code: (ii) x, y+1, z.