trans-Dichloridobis{[4-(dimethyl-amino)-phen-yl]diphenyl-phosphane}palladium(II).

The title compound, trans-[PdCl(2){PPh(2)(4-Me(2)NC(6)H(4))}(2)], crystallizes with the Pd atom on a center of symmetry, resulting in a distorted trans-PdCl(2)P(2) square-planar geometry. The Pd-P and Pd-Cl bond lengths are 2.3550 (7) and 2.2906 (7) Å, respectively. Some weak inter-actions are observed between the aromatic rings of adjacent mol-ecules, with an inter-planar distance between two π-stacked rings of 3.505 (3) Å. Intra- and intermolecular C-H⋯Cl hydrogen bonds also occur.

Related literature

For a review on related compounds, see: Spessard & Miessler (1996 ▶). For related compounds, see: Burrow et al. (1994 ▶); DiMeglio et al. (1990 ▶); Edwards et al. (1998 ▶); Ferguson et al. (1982 ▶); Grushin et al. (1994 ▶); Kitano et al. (1983 ▶); Leznoff et al. (1999 ▶); Meij et al. (2003 ▶); Meijboom et al. (2006a ▶,b ▶); Meijboom & Omondi (2010 ▶). For the synthesis of the starting materials, see: Drew & Doyle (1990 ▶).

Experimental

Crystal data

[PdCl2(C20H20NP)2]

M = 787.98

Triclinic,

a = 9.9006 (16) Å

b = 9.9815 (15) Å

c = 10.4021 (14) Å

α = 86.291 (4)°

β = 69.135 (4)°

γ = 65.383 (4)°

V = 869.0 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.81 mm−1

T = 100 K

0.18 × 0.10 × 0.04 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker; 2004 ▶) T min = 0.870, T max = 0.966

10917 measured reflections

4268 independent reflections

3545 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.096

S = 1.05

4268 reflections

216 parameters

H-atom parameters constrained

Δρmax = 2.04 e Å−3

Δρmin = −0.72 e Å−3

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, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042595/pk2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042595/pk2275Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[PdCl2(C20H20NP)2]	Z = 1
Mr = 787.98	F(000) = 404
Triclinic, P1	Dx = 1.506 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9006 (16) Å	Cell parameters from 3426 reflections
b = 9.9815 (15) Å	θ = 2.3–28.1°
c = 10.4021 (14) Å	µ = 0.81 mm−1
α = 86.291 (4)°	T = 100 K
β = 69.135 (4)°	Plate, yellow
γ = 65.383 (4)°	0.18 × 0.1 × 0.04 mm
V = 869.0 (2) Å3

Bruker X8 APEXII 4K Kappa CCD diffractometer	4268 independent reflections
Radiation source: fine-focus sealed tube	3545 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 8.4 pixels mm-1	θmax = 28.3°, θmin = 2.3°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker; 2004)	k = −13→12
Tmin = 0.870, Tmax = 0.966	l = −13→13
10917 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.5716P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 2.04 e Å−3
4268 reflections	Δρmin = −0.72 e Å−3
216 parameters

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 50 s/frame. A total of 604 frames were collected with a frame width of 0.5° covering up to θ = 28.28° with 99.0% completeness accomplished.

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
Pd	0.5	0.5	0.5	0.01593 (10)
Cl	0.62710 (9)	0.24815 (7)	0.44885 (7)	0.02265 (16)
P	0.29234 (9)	0.49076 (7)	0.69623 (6)	0.01476 (15)
C11	0.2478 (3)	0.6133 (3)	0.8410 (2)	0.0151 (5)
C12	0.0928 (3)	0.7106 (3)	0.9190 (3)	0.0172 (5)
H12	0.0075	0.7163	0.8936	0.021*
C13	0.0600 (3)	0.7997 (3)	1.0331 (3)	0.0172 (5)
H13	−0.047	0.8665	1.0836	0.021*
C14	0.1827 (3)	0.7926 (3)	1.0749 (3)	0.0178 (6)
C15	0.3404 (3)	0.6938 (3)	0.9942 (3)	0.0180 (6)
H15	0.4266	0.6857	1.0195	0.022*
C16	0.3700 (3)	0.6091 (3)	0.8791 (3)	0.0186 (6)
H16	0.4771	0.5463	0.8245	0.022*
N	0.1501 (3)	0.8796 (3)	1.1885 (3)	0.0266 (6)
C1	−0.0146 (4)	0.9674 (3)	1.2752 (3)	0.0255 (6)
H1A	−0.0691	1.0378	1.2204	0.038*
H1B	−0.0181	1.0218	1.3523	0.038*
H1C	−0.0679	0.902	1.3113	0.038*
C2	0.2712 (4)	0.8525 (4)	1.2451 (3)	0.0322 (7)
H2A	0.3102	0.75	1.2684	0.048*
H2B	0.226	0.9202	1.3287	0.048*
H2C	0.3597	0.8689	1.1768	0.048*
C21	0.3219 (3)	0.3123 (3)	0.7667 (3)	0.0170 (5)
C22	0.3088 (3)	0.2961 (3)	0.9042 (3)	0.0198 (6)
H22	0.2843	0.3788	0.9627	0.024*
C23	0.3316 (4)	0.1597 (3)	0.9563 (3)	0.0250 (6)
H23	0.3219	0.1496	1.0502	0.03*
C24	0.3682 (4)	0.0391 (3)	0.8717 (4)	0.0287 (7)
H24	0.3867	−0.0547	0.9067	0.034*
C25	0.3781 (4)	0.0548 (3)	0.7352 (3)	0.0264 (7)
H25	0.4008	−0.0278	0.6776	0.032*
C26	0.3549 (3)	0.1904 (3)	0.6835 (3)	0.0208 (6)
H26	0.3616	0.2005	0.5902	0.025*
C31	0.1021 (3)	0.5480 (3)	0.6741 (3)	0.0171 (5)
C32	−0.0064 (4)	0.4905 (3)	0.7501 (3)	0.0206 (6)
H32	0.0225	0.4163	0.8095	0.025*
C33	−0.1543 (4)	0.5394 (3)	0.7404 (3)	0.0249 (6)
H33	−0.2256	0.4979	0.792	0.03*
C34	−0.1998 (4)	0.6491 (4)	0.6554 (3)	0.0275 (7)
H34	−0.3023	0.6842	0.6495	0.033*
C35	−0.0932 (4)	0.7064 (4)	0.5797 (3)	0.0290 (7)
H35	−0.1235	0.7817	0.5217	0.035*
C36	0.0567 (4)	0.6564 (3)	0.5868 (3)	0.0238 (6)
H36	0.1289	0.6957	0.5323	0.029*

	U11	U22	U33	U12	U13	U23
Pd	0.02125 (18)	0.01026 (15)	0.01176 (14)	−0.00809 (12)	0.00111 (11)	−0.00095 (10)
Cl	0.0274 (4)	0.0115 (3)	0.0198 (3)	−0.0082 (3)	0.0023 (3)	−0.0020 (2)
P	0.0190 (4)	0.0113 (3)	0.0110 (3)	−0.0080 (3)	−0.0001 (3)	−0.0002 (2)
C11	0.0219 (15)	0.0096 (12)	0.0116 (11)	−0.0085 (11)	−0.0013 (10)	0.0007 (9)
C12	0.0181 (14)	0.0165 (13)	0.0155 (12)	−0.0089 (12)	−0.0025 (11)	0.0003 (10)
C13	0.0159 (14)	0.0130 (13)	0.0156 (12)	−0.0049 (11)	0.0011 (10)	−0.0024 (10)
C14	0.0227 (15)	0.0111 (13)	0.0165 (12)	−0.0079 (11)	−0.0025 (11)	−0.0005 (10)
C15	0.0171 (14)	0.0173 (14)	0.0186 (12)	−0.0079 (12)	−0.0041 (11)	−0.0005 (10)
C16	0.0186 (15)	0.0143 (13)	0.0177 (12)	−0.0071 (11)	−0.0003 (11)	0.0001 (10)
N	0.0215 (14)	0.0294 (14)	0.0234 (12)	−0.0073 (12)	−0.0032 (11)	−0.0139 (10)
C1	0.0247 (17)	0.0260 (16)	0.0175 (13)	−0.0061 (13)	−0.0026 (12)	−0.0067 (11)
C2	0.0291 (18)	0.039 (2)	0.0296 (16)	−0.0137 (16)	−0.0112 (14)	−0.0086 (14)
C21	0.0169 (14)	0.0135 (13)	0.0169 (12)	−0.0085 (11)	0.0001 (11)	0.0018 (10)
C22	0.0186 (15)	0.0200 (14)	0.0195 (13)	−0.0090 (12)	−0.0047 (11)	0.0037 (11)
C23	0.0216 (16)	0.0255 (16)	0.0295 (15)	−0.0125 (13)	−0.0096 (13)	0.0123 (13)
C24	0.0210 (16)	0.0168 (15)	0.0468 (19)	−0.0091 (13)	−0.0113 (14)	0.0144 (14)
C25	0.0216 (16)	0.0154 (14)	0.0377 (17)	−0.0096 (13)	−0.0032 (13)	−0.0012 (12)
C26	0.0206 (15)	0.0155 (14)	0.0225 (13)	−0.0090 (12)	−0.0016 (12)	0.0000 (11)
C31	0.0227 (15)	0.0137 (13)	0.0129 (11)	−0.0073 (11)	−0.0042 (11)	−0.0019 (10)
C32	0.0259 (16)	0.0189 (14)	0.0155 (12)	−0.0099 (13)	−0.0052 (11)	0.0024 (10)
C33	0.0282 (17)	0.0269 (16)	0.0216 (14)	−0.0152 (14)	−0.0069 (13)	0.0010 (12)
C34	0.0292 (18)	0.0280 (17)	0.0269 (15)	−0.0102 (14)	−0.0139 (13)	−0.0001 (13)
C35	0.0373 (19)	0.0247 (16)	0.0285 (15)	−0.0116 (15)	−0.0184 (15)	0.0074 (13)
C36	0.0331 (18)	0.0219 (15)	0.0183 (13)	−0.0150 (14)	−0.0077 (12)	0.0040 (11)

Pd—Cli	2.2906 (7)	C2—H2B	0.98
Pd—Cl	2.2906 (7)	C2—H2C	0.98
Pd—Pi	2.3550 (7)	C21—C26	1.393 (4)
Pd—P	2.3550 (7)	C21—C22	1.395 (4)
P—C11	1.809 (3)	C22—C23	1.391 (4)
P—C31	1.823 (3)	C22—H22	0.95
P—C21	1.829 (3)	C23—C24	1.379 (5)
C11—C16	1.385 (4)	C23—H23	0.95
C11—C12	1.389 (4)	C24—C25	1.391 (5)
C12—C13	1.388 (4)	C24—H24	0.95
C12—H12	0.95	C25—C26	1.382 (4)
C13—C14	1.404 (4)	C25—H25	0.95
C13—H13	0.95	C26—H26	0.95
C14—N	1.372 (3)	C31—C36	1.398 (4)
C14—C15	1.416 (4)	C31—C32	1.400 (4)
C15—C16	1.382 (4)	C32—C33	1.377 (4)
C15—H15	0.95	C32—H32	0.95
C16—H16	0.95	C33—C34	1.390 (4)
N—C2	1.438 (4)	C33—H33	0.95
N—C1	1.451 (4)	C34—C35	1.384 (5)
C1—H1A	0.98	C34—H34	0.95
C1—H1B	0.98	C35—C36	1.383 (4)
C1—H1C	0.98	C35—H35	0.95
C2—H2A	0.98	C36—H36	0.95
Cli—Pd—Cl	180.0000 (10)	H2A—C2—H2B	109.5
Cli—Pd—Pi	93.84 (2)	N—C2—H2C	109.5
Cl—Pd—Pi	86.16 (2)	H2A—C2—H2C	109.5
Cli—Pd—P	86.16 (2)	H2B—C2—H2C	109.5
Cl—Pd—P	93.84 (2)	C26—C21—C22	118.8 (2)
Pi—Pd—P	180.0000 (10)	C26—C21—P	120.1 (2)
C11—P—C31	104.37 (12)	C22—C21—P	121.1 (2)
C11—P—C21	104.02 (12)	C23—C22—C21	120.4 (3)
C31—P—C21	102.69 (13)	C23—C22—H22	119.8
C11—P—Pd	111.57 (9)	C21—C22—H22	119.8
C31—P—Pd	114.91 (8)	C24—C23—C22	120.1 (3)
C21—P—Pd	117.81 (9)	C24—C23—H23	120
C16—C11—C12	118.0 (2)	C22—C23—H23	120
C16—C11—P	119.9 (2)	C23—C24—C25	120.0 (3)
C12—C11—P	122.1 (2)	C23—C24—H24	120
C13—C12—C11	121.4 (3)	C25—C24—H24	120
C13—C12—H12	119.3	C26—C25—C24	120.0 (3)
C11—C12—H12	119.3	C26—C25—H25	120
C12—C13—C14	120.9 (3)	C24—C25—H25	120
C12—C13—H13	119.6	C25—C26—C21	120.7 (3)
C14—C13—H13	119.6	C25—C26—H26	119.7
N—C14—C13	120.9 (3)	C21—C26—H26	119.7
N—C14—C15	121.8 (3)	C36—C31—C32	118.2 (3)
C13—C14—C15	117.3 (2)	C36—C31—P	121.0 (2)
C16—C15—C14	120.5 (3)	C32—C31—P	120.7 (2)
C16—C15—H15	119.7	C33—C32—C31	121.2 (3)
C14—C15—H15	119.7	C33—C32—H32	119.4
C15—C16—C11	121.8 (3)	C31—C32—H32	119.4
C15—C16—H16	119.1	C32—C33—C34	120.3 (3)
C11—C16—H16	119.1	C32—C33—H33	119.8
C14—N—C2	120.2 (3)	C34—C33—H33	119.8
C14—N—C1	119.3 (3)	C35—C34—C33	118.8 (3)
C2—N—C1	118.0 (2)	C35—C34—H34	120.6
N—C1—H1A	109.5	C33—C34—H34	120.6
N—C1—H1B	109.5	C36—C35—C34	121.4 (3)
H1A—C1—H1B	109.5	C36—C35—H35	119.3
N—C1—H1C	109.5	C34—C35—H35	119.3
H1A—C1—H1C	109.5	C35—C36—C31	120.0 (3)
H1B—C1—H1C	109.5	C35—C36—H36	120
N—C2—H2A	109.5	C31—C36—H36	120
N—C2—H2B	109.5
Cli—Pd—P—C11	−44.26 (10)	C31—P—C21—C26	69.8 (3)
Cl—Pd—P—C11	135.74 (10)	Pd—P—C21—C26	−57.5 (3)
Cli—Pd—P—C31	74.28 (10)	C11—P—C21—C22	−0.3 (3)
Cl—Pd—P—C31	−105.72 (10)	C31—P—C21—C22	−108.9 (2)
Cli—Pd—P—C21	−164.46 (11)	Pd—P—C21—C22	123.7 (2)
Cl—Pd—P—C21	15.54 (11)	C26—C21—C22—C23	1.2 (4)
C31—P—C11—C16	−174.3 (2)	P—C21—C22—C23	180.0 (2)
C21—P—C11—C16	78.4 (2)	C21—C22—C23—C24	0.4 (4)
Pd—P—C11—C16	−49.7 (2)	C22—C23—C24—C25	−1.8 (5)
C31—P—C11—C12	7.3 (2)	C23—C24—C25—C26	1.5 (5)
C21—P—C11—C12	−100.1 (2)	C24—C25—C26—C21	0.1 (5)
Pd—P—C11—C12	131.93 (19)	C22—C21—C26—C25	−1.5 (4)
C16—C11—C12—C13	−1.0 (4)	P—C21—C26—C25	179.7 (2)
P—C11—C12—C13	177.4 (2)	C11—P—C31—C36	90.4 (2)
C11—C12—C13—C14	−1.0 (4)	C21—P—C31—C36	−161.3 (2)
C12—C13—C14—N	−179.3 (3)	Pd—P—C31—C36	−32.1 (3)
C12—C13—C14—C15	1.4 (4)	C11—P—C31—C32	−86.0 (2)
N—C14—C15—C16	−179.0 (3)	C21—P—C31—C32	22.3 (2)
C13—C14—C15—C16	0.2 (4)	Pd—P—C31—C32	151.50 (19)
C14—C15—C16—C11	−2.3 (4)	C36—C31—C32—C33	−0.4 (4)
C12—C11—C16—C15	2.7 (4)	P—C31—C32—C33	176.1 (2)
P—C11—C16—C15	−175.8 (2)	C31—C32—C33—C34	−0.8 (4)
C13—C14—N—C2	168.6 (3)	C32—C33—C34—C35	0.9 (5)
C15—C14—N—C2	−12.2 (4)	C33—C34—C35—C36	0.2 (5)
C13—C14—N—C1	7.0 (4)	C34—C35—C36—C31	−1.4 (5)
C15—C14—N—C1	−173.8 (3)	C32—C31—C36—C35	1.5 (4)
C11—P—C21—C26	178.4 (2)	P—C31—C36—C35	−175.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···Clii	0.95	2.79	3.710 (3)	163
C26—H26···Cl	0.95	2.74	3.159 (3)	108
C36—H36···Cli	0.95	2.77	3.529 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯Cli	0.95	2.79	3.710 (3)	163
C26—H26⋯Cl	0.95	2.74	3.159 (3)	108
C36—H36⋯Clii	0.95	2.77	3.529 (3)	138

Symmetry codes: (i) ; (ii) .