trans-Dichloridobis[dicyclo-hex-yl(phen-yl)phosphane-κP]palladium(II).

The title compound, [PdCl(2){P(C(6)H(11))(2)(C(6)H(5))}(2)], forms a monomeric complex with a trans-square-planar geometry. The Pd-P bond lengths are 2.3343 (5) Å, as the Pd atom lies on an inversion centre, while the Pd-Cl bond lengths are 2.3017 (4) Å. The observed structure was found to be closely related to [PdCl(2){P(C(6)H(11))(3)}(2)] [Grushin et al. (1994 ▶). Inorg. Chem.33, 4804-4806], [PdBr(2){P(C(6)H(11))(3)}(2)] [Clarke et al. (2003 ▶). Dalton Trans. pp. 4393-4394] and [PdCl(2)P(C(6)H(11))(2)(C(7)H(7))}(2)] [Vuoti et al. (2008 ▶). Eur. J. Inorg. Chem. pp. 397-407] (C(6)H(11) is cyclo-hexyl and C(7)H(7) is o-tol-yl). One of the cyclo-hexyl rings is disordered with the phenyl ring in a 0.587 (9):413 (9) ratio. Five long-range C-H⋯Cl inter-actions were observed within the structure.

Related literature

For a review on related compounds, see: Spessard & Miessler (1996 ▶). For the synthesis of the starting materials, see: Drew & Doyle (1990 ▶). For similar R-P2PdCl2 compounds, see: Ogutu & Meijboom (2011 ▶); Muller & Meijboom (2010a ▶,b ▶). For their applications, see: Bedford et al. (2004 ▶).

Experimental

Crystal data

[PdCl2(C18H27P)2]

M = 726.03

Triclinic,

a = 9.439 (4) Å

b = 10.095 (4) Å

c = 10.623 (5) Å

α = 113.115 (2)°

β = 107.321 (2)°

γ = 91.625 (2)°

V = 876.5 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.80 mm−1

T = 100 K

0.27 × 0.13 × 0.11 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.885, T max = 0.918

12144 measured reflections

2931 independent reflections

2891 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.051

S = 1.19

2931 reflections

266 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812010100/zl2455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010100/zl2455Isup2.hkl

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

[PdCl2(C18H27P)2]	Z = 1
Mr = 726.03	F(000) = 380
Triclinic, P1	Dx = 1.375 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.439 (4) Å	Cell parameters from 9929 reflections
b = 10.095 (4) Å	θ = 2.2–24.9°
c = 10.623 (5) Å	µ = 0.80 mm−1
α = 113.115 (2)°	T = 100 K
β = 107.321 (2)°	Conical, yellow
γ = 91.625 (2)°	0.27 × 0.13 × 0.11 mm
V = 876.5 (7) Å3

Bruker X8 APEXII 4K KappaCCD diffractometer	2931 independent reflections
Radiation source: fine-focus sealed tube	2891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 24.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
Tmin = 0.885, Tmax = 0.918	k = −11→11
12144 measured reflections	l = −11→12

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0125P)2 + 0.5911P] where P = (Fo2 + 2Fc2)/3
2931 reflections	(Δ/σ)max = 0.001
266 parameters	Δρmax = 0.37 e Å−3
12 restraints	Δρmin = −0.38 e Å−3

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A collection frame width of 0.5° covering up to θ = 24.9° resulted in 97% completeness accomplished.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.8288 (11)	−0.1156 (10)	0.6237 (7)	0.0215 (7)	0.587 (9)
C2	0.9177 (12)	−0.2245 (12)	0.6081 (9)	0.025 (3)	0.587 (9)
H2	0.9665	−0.2441	0.6874	0.030*	0.587 (9)
C3	0.9336 (9)	−0.3042 (9)	0.4741 (10)	0.030 (3)	0.587 (9)
H3	0.9931	−0.3770	0.4637	0.036*	0.587 (9)
C4	0.8606 (8)	−0.2749 (8)	0.3556 (8)	0.038 (2)	0.587 (9)
H4	0.8713	−0.3282	0.2660	0.045*	0.587 (9)
C5	0.7718 (9)	−0.1660 (9)	0.3712 (7)	0.040 (4)	0.587 (9)
H5	0.7229	−0.1465	0.2920	0.048*	0.587 (9)
C6	0.7558 (7)	−0.0864 (7)	0.5053 (8)	0.0294 (15)	0.587 (9)
H6	0.6964	−0.0135	0.5157	0.035*	0.587 (9)
C1B	0.8337 (16)	−0.1023 (17)	0.6235 (11)	0.0215 (7)	0.413 (9)
H1B	0.9155	−0.0324	0.6342	0.026*	0.413 (9)
C2B	0.892 (2)	−0.2484 (19)	0.5907 (14)	0.021 (3)	0.413 (9)
H2BA	0.8132	−0.3233	0.5748	0.025*	0.413 (9)
H2BB	0.9771	−0.2397	0.6732	0.025*	0.413 (9)
C3B	0.9388 (17)	−0.2926 (17)	0.4549 (15)	0.027 (3)	0.413 (9)
H3BA	1.0238	−0.2223	0.4747	0.033*	0.413 (9)
H3BB	0.9705	−0.3873	0.4327	0.033*	0.413 (9)
C4B	0.8129 (12)	−0.2994 (11)	0.3271 (10)	0.023 (2)	0.413 (9)
H4BA	0.7318	−0.3765	0.3012	0.027*	0.413 (9)
H4BB	0.8477	−0.3228	0.2448	0.027*	0.413 (9)
C5B	0.7549 (14)	−0.1569 (12)	0.3589 (11)	0.023 (3)	0.413 (9)
H5BA	0.6712	−0.1655	0.2751	0.028*	0.413 (9)
H5BB	0.8337	−0.0811	0.3773	0.028*	0.413 (9)
C6B	0.7032 (10)	−0.1141 (10)	0.4917 (11)	0.0224 (18)	0.413 (9)
H6BA	0.6677	−0.0212	0.5118	0.027*	0.413 (9)
H6BB	0.6207	−0.1871	0.4718	0.027*	0.413 (9)
C7	0.7420 (2)	0.1499 (2)	0.8114 (2)	0.0247 (4)
H7	0.6498	0.1300	0.7292	0.030*
C8	0.8584 (3)	0.2478 (2)	0.8001 (2)	0.0335 (5)
H8A	0.8772	0.1976	0.7093	0.040*
H8B	0.9522	0.2690	0.8792	0.040*
C9	0.8040 (3)	0.3903 (2)	0.8064 (2)	0.0355 (5)
H9A	0.8816	0.4529	0.8034	0.043*
H9B	0.7152	0.3697	0.7224	0.043*
C10	0.7666 (3)	0.4687 (2)	0.9438 (2)	0.0353 (5)
H10A	0.8579	0.4988	1.0275	0.042*
H10B	0.7267	0.5558	0.9424	0.042*
C11	0.6531 (3)	0.3725 (2)	0.9585 (3)	0.0365 (5)
H11A	0.5577	0.3531	0.8818	0.044*
H11B	0.6378	0.4236	1.0508	0.044*
C12	0.7038 (2)	0.2278 (2)	0.9498 (2)	0.0288 (4)
H12A	0.6242	0.1658	0.9509	0.035*
H12B	0.7916	0.2459	1.0339	0.035*
C13	0.6240 (7)	−0.1337 (11)	0.7724 (14)	0.017 (2)	0.587 (9)
H13	0.6085	−0.0958	0.8667	0.020*	0.587 (9)
C14	0.4830 (6)	−0.1221 (6)	0.6629 (6)	0.0260 (12)	0.587 (9)
H14A	0.4726	−0.0202	0.6898	0.031*	0.587 (9)
H14B	0.4928	−0.1611	0.5672	0.031*	0.587 (9)
C15	0.3432 (8)	−0.2058 (7)	0.6579 (13)	0.038 (2)	0.587 (9)
H15A	0.3289	−0.1617	0.7515	0.046*	0.587 (9)
H15B	0.2557	−0.1994	0.5855	0.046*	0.587 (9)
C16	0.3565 (8)	−0.3654 (7)	0.6210 (8)	0.0311 (14)	0.587 (9)
H16A	0.2694	−0.4143	0.6255	0.037*	0.587 (9)
H16B	0.3591	−0.4128	0.5228	0.037*	0.587 (9)
C17	0.4985 (10)	−0.3777 (10)	0.7268 (16)	0.029 (2)	0.587 (9)
H17A	0.5083	−0.4798	0.6985	0.035*	0.587 (9)
H17B	0.4903	−0.3397	0.8232	0.035*	0.587 (9)
C18	0.6381 (8)	−0.2948 (9)	0.7318 (17)	0.023 (3)	0.587 (9)
H18A	0.6513	−0.3373	0.6377	0.028*	0.587 (9)
H18B	0.7258	−0.3027	0.8029	0.028*	0.587 (9)
C13B	0.6193 (7)	−0.1534 (11)	0.7533 (16)	0.027 (5)	0.413 (9)
C14B	0.4787 (8)	−0.1111 (7)	0.7229 (11)	0.0331 (19)	0.413 (9)
H14C	0.4707	−0.0176	0.7283	0.040*	0.413 (9)
C15B	0.3501 (7)	−0.2087 (9)	0.6846 (13)	0.045 (5)	0.413 (9)
H15C	0.2560	−0.1804	0.6642	0.054*	0.413 (9)
C16B	0.3620 (11)	−0.3485 (8)	0.6766 (10)	0.033 (2)	0.413 (9)
H16C	0.2760	−0.4137	0.6509	0.040*	0.413 (9)
C17B	0.5026 (14)	−0.3907 (9)	0.7070 (17)	0.035 (5)	0.413 (9)
H17C	0.5106	−0.4843	0.7016	0.042*	0.413 (9)
C18B	0.6312 (10)	−0.2932 (14)	0.745 (2)	0.032 (6)	0.413 (9)
H18C	0.7253	−0.3215	0.7657	0.038*	0.413 (9)
P1	0.79648 (5)	−0.02795 (5)	0.79688 (5)	0.01688 (11)
Cl1	1.15978 (5)	0.06458 (5)	0.89925 (5)	0.02496 (11)
Pd1	1.0000	0.0000	1.0000	0.01502 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0227 (11)	0.0238 (17)	0.0172 (9)	0.0024 (11)	0.0065 (8)	0.0079 (9)
C2	0.022 (4)	0.026 (4)	0.022 (3)	−0.002 (3)	0.004 (3)	0.006 (3)
C3	0.024 (3)	0.030 (3)	0.027 (4)	0.001 (2)	0.006 (3)	0.005 (3)
C4	0.032 (5)	0.046 (4)	0.025 (4)	−0.004 (3)	0.017 (3)	0.001 (3)
C5	0.040 (5)	0.059 (7)	0.024 (4)	0.000 (4)	0.009 (3)	0.022 (4)
C6	0.030 (4)	0.033 (3)	0.029 (3)	0.005 (3)	0.012 (3)	0.015 (2)
C1B	0.0227 (11)	0.0238 (17)	0.0172 (9)	0.0024 (11)	0.0065 (8)	0.0079 (9)
C2B	0.022 (5)	0.020 (5)	0.016 (4)	0.005 (5)	0.004 (3)	0.006 (3)
C3B	0.036 (6)	0.034 (5)	0.018 (5)	0.015 (4)	0.016 (4)	0.012 (4)
C4B	0.027 (5)	0.026 (4)	0.015 (3)	0.001 (4)	0.007 (4)	0.009 (3)
C5B	0.033 (5)	0.023 (5)	0.012 (4)	0.008 (4)	0.007 (3)	0.006 (4)
C6B	0.023 (5)	0.026 (4)	0.016 (3)	0.003 (3)	0.002 (4)	0.010 (3)
C7	0.0291 (10)	0.0221 (9)	0.0232 (9)	0.0069 (8)	0.0079 (8)	0.0102 (8)
C8	0.0487 (13)	0.0264 (10)	0.0347 (11)	0.0097 (9)	0.0222 (10)	0.0158 (9)
C9	0.0496 (14)	0.0271 (10)	0.0358 (12)	0.0089 (9)	0.0148 (10)	0.0187 (9)
C10	0.0481 (14)	0.0232 (10)	0.0356 (11)	0.0112 (9)	0.0138 (10)	0.0130 (9)
C11	0.0446 (13)	0.0268 (10)	0.0399 (12)	0.0117 (9)	0.0209 (11)	0.0106 (9)
C12	0.0359 (11)	0.0230 (9)	0.0298 (10)	0.0055 (8)	0.0158 (9)	0.0098 (8)
C13	0.023 (4)	0.013 (2)	0.013 (3)	0.0053 (19)	0.002 (2)	0.007 (2)
C14	0.024 (2)	0.029 (2)	0.028 (3)	0.0036 (15)	0.007 (2)	0.017 (2)
C15	0.033 (4)	0.026 (4)	0.054 (3)	0.008 (3)	0.009 (3)	0.019 (3)
C16	0.027 (2)	0.031 (2)	0.034 (4)	−0.0029 (17)	0.008 (3)	0.016 (2)
C17	0.025 (5)	0.025 (4)	0.043 (4)	0.003 (3)	0.013 (3)	0.019 (3)
C18	0.019 (4)	0.020 (5)	0.031 (4)	−0.004 (3)	0.008 (3)	0.011 (3)
C13B	0.020 (5)	0.033 (8)	0.021 (6)	−0.005 (4)	0.010 (4)	0.004 (4)
C14B	0.034 (3)	0.026 (3)	0.044 (5)	0.007 (2)	0.018 (4)	0.015 (4)
C15B	0.011 (5)	0.063 (9)	0.065 (8)	0.003 (4)	0.011 (4)	0.034 (5)
C16B	0.036 (4)	0.036 (4)	0.029 (5)	−0.003 (3)	0.014 (4)	0.012 (4)
C17B	0.043 (9)	0.023 (6)	0.039 (7)	0.001 (5)	0.015 (5)	0.011 (4)
C18B	0.041 (9)	0.031 (8)	0.034 (7)	0.020 (6)	0.017 (6)	0.020 (6)
P1	0.0191 (2)	0.0180 (2)	0.0148 (2)	0.00359 (17)	0.00545 (18)	0.00827 (17)
Cl1	0.0231 (2)	0.0357 (2)	0.0193 (2)	0.00003 (18)	0.00788 (18)	0.01451 (19)
Pd1	0.01700 (11)	0.01711 (11)	0.01244 (10)	0.00288 (7)	0.00508 (7)	0.00760 (7)

C1—C2	1.3900	C10—H10A	0.9700
C1—C6	1.3900	C10—H10B	0.9700
C1—P1	1.825 (7)	C11—C12	1.527 (3)
C2—C3	1.3900	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.3900	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.3900	C13—C14	1.528 (8)
C4—H4	0.9300	C13—C18	1.531 (9)
C5—C6	1.3900	C13—P1	1.813 (7)
C5—H5	0.9300	C13—H13	0.9800
C6—H6	0.9300	C14—C15	1.523 (8)
C1B—C6B	1.524 (10)	C14—H14A	0.9700
C1B—C2B	1.534 (9)	C14—H14B	0.9700
C1B—P1	1.843 (10)	C15—C16	1.519 (7)
C1B—H1B	0.9800	C15—H15A	0.9700
C2B—C3B	1.538 (11)	C15—H15B	0.9700
C2B—H2BA	0.9700	C16—C17	1.516 (10)
C2B—H2BB	0.9700	C16—H16A	0.9700
C3B—C4B	1.491 (12)	C16—H16B	0.9700
C3B—H3BA	0.9700	C17—C18	1.517 (8)
C3B—H3BB	0.9700	C17—H17A	0.9700
C4B—C5B	1.503 (10)	C17—H17B	0.9700
C4B—H4BA	0.9700	C18—H18A	0.9700
C4B—H4BB	0.9700	C18—H18B	0.9700
C5B—C6B	1.536 (9)	C13B—C14B	1.3900
C5B—H5BA	0.9700	C13B—C18B	1.3900
C5B—H5BB	0.9700	C13B—P1	1.891 (7)
C6B—H6BA	0.9700	C14B—C15B	1.3900
C6B—H6BB	0.9700	C14B—H14C	0.9300
C7—C8	1.520 (3)	C15B—C16B	1.3900
C7—C12	1.528 (3)	C15B—H15C	0.9300
C7—P1	1.8421 (19)	C16B—C17B	1.3900
C7—H7	0.9800	C16B—H16C	0.9300
C8—C9	1.524 (3)	C17B—C18B	1.3900
C8—H8A	0.9700	C17B—H17C	0.9300
C8—H8B	0.9700	C18B—H18C	0.9300
C9—C10	1.516 (3)	P1—Pd1	2.3343 (5)
C9—H9A	0.9700	Cl1—Pd1	2.3017 (4)
C9—H9B	0.9700	Pd1—Cl1i	2.3017 (4)
C10—C11	1.507 (3)	Pd1—P1i	2.3343 (5)
C2—C1—C6	120.0	C12—C11—H11B	109.2
C2—C1—P1	117.9 (5)	H11A—C11—H11B	107.9
C6—C1—P1	121.8 (5)	C11—C12—C7	110.85 (17)
C1—C2—C3	120.0	C11—C12—H12A	109.5
C1—C2—H2	120.0	C7—C12—H12A	109.5
C3—C2—H2	120.0	C11—C12—H12B	109.5
C4—C3—C2	120.0	C7—C12—H12B	109.5
C4—C3—H3	120.0	H12A—C12—H12B	108.1
C2—C3—H3	120.0	C14—C13—C18	109.4 (6)
C3—C4—C5	120.0	C14—C13—P1	114.9 (5)
C3—C4—H4	120.0	C18—C13—P1	111.5 (5)
C5—C4—H4	120.0	C14—C13—H13	106.9
C6—C5—C4	120.0	C18—C13—H13	106.9
C6—C5—H5	120.0	P1—C13—H13	106.9
C4—C5—H5	120.0	C15—C14—C13	110.9 (6)
C5—C6—C1	120.0	C15—C14—H14A	109.5
C5—C6—H6	120.0	C13—C14—H14A	109.5
C1—C6—H6	120.0	C15—C14—H14B	109.5
C6B—C1B—C2B	109.7 (7)	C13—C14—H14B	109.5
C6B—C1B—P1	114.9 (8)	H14A—C14—H14B	108.0
C2B—C1B—P1	113.6 (8)	C16—C15—C14	111.4 (5)
C6B—C1B—H1B	106.0	C16—C15—H15A	109.4
C2B—C1B—H1B	106.0	C14—C15—H15A	109.4
P1—C1B—H1B	106.0	C16—C15—H15B	109.4
C1B—C2B—C3B	110.2 (6)	C14—C15—H15B	109.4
C1B—C2B—H2BA	109.6	H15A—C15—H15B	108.0
C3B—C2B—H2BA	109.6	C17—C16—C15	110.2 (6)
C1B—C2B—H2BB	109.6	C17—C16—H16A	109.6
C3B—C2B—H2BB	109.6	C15—C16—H16A	109.6
H2BA—C2B—H2BB	108.1	C17—C16—H16B	109.6
C4B—C3B—C2B	111.5 (7)	C15—C16—H16B	109.6
C4B—C3B—H3BA	109.3	H16A—C16—H16B	108.1
C2B—C3B—H3BA	109.3	C16—C17—C18	112.1 (6)
C4B—C3B—H3BB	109.3	C16—C17—H17A	109.2
C2B—C3B—H3BB	109.3	C18—C17—H17A	109.2
H3BA—C3B—H3BB	108.0	C16—C17—H17B	109.2
C3B—C4B—C5B	111.3 (8)	C18—C17—H17B	109.2
C3B—C4B—H4BA	109.4	H17A—C17—H17B	107.9
C5B—C4B—H4BA	109.4	C17—C18—C13	110.4 (6)
C3B—C4B—H4BB	109.4	C17—C18—H18A	109.6
C5B—C4B—H4BB	109.4	C13—C18—H18A	109.6
H4BA—C4B—H4BB	108.0	C17—C18—H18B	109.6
C4B—C5B—C6B	110.8 (7)	C13—C18—H18B	109.6
C4B—C5B—H5BA	109.5	H18A—C18—H18B	108.1
C6B—C5B—H5BA	109.5	C14B—C13B—C18B	120.0
C4B—C5B—H5BB	109.5	C14B—C13B—P1	121.5 (5)
C6B—C5B—H5BB	109.5	C18B—C13B—P1	118.4 (5)
H5BA—C5B—H5BB	108.1	C15B—C14B—C13B	120.0
C1B—C6B—C5B	109.8 (8)	C15B—C14B—H14C	120.0
C1B—C6B—H6BA	109.7	C13B—C14B—H14C	120.0
C5B—C6B—H6BA	109.7	C16B—C15B—C14B	120.0
C1B—C6B—H6BB	109.7	C16B—C15B—H15C	120.0
C5B—C6B—H6BB	109.7	C14B—C15B—H15C	120.0
H6BA—C6B—H6BB	108.2	C15B—C16B—C17B	120.0
C8—C7—C12	111.13 (16)	C15B—C16B—H16C	120.0
C8—C7—P1	113.28 (14)	C17B—C16B—H16C	120.0
C12—C7—P1	111.08 (13)	C18B—C17B—C16B	120.0
C8—C7—H7	107.0	C18B—C17B—H17C	120.0
C12—C7—H7	107.0	C16B—C17B—H17C	120.0
P1—C7—H7	107.0	C17B—C18B—C13B	120.0
C7—C8—C9	110.74 (18)	C17B—C18B—H18C	120.0
C7—C8—H8A	109.5	C13B—C18B—H18C	120.0
C9—C8—H8A	109.5	C13—P1—C1	104.6 (6)
C7—C8—H8B	109.5	C13—P1—C7	103.3 (3)
C9—C8—H8B	109.5	C1—P1—C7	107.4 (3)
H8A—C8—H8B	108.1	C13—P1—C1B	108.0 (6)
C10—C9—C8	111.03 (17)	C7—P1—C1B	103.5 (5)
C10—C9—H9A	109.4	C1—P1—C13B	98.7 (5)
C8—C9—H9A	109.4	C7—P1—C13B	106.9 (3)
C10—C9—H9B	109.4	C1B—P1—C13B	102.1 (7)
C8—C9—H9B	109.4	C13—P1—Pd1	115.0 (3)
H9A—C9—H9B	108.0	C1—P1—Pd1	114.7 (3)
C11—C10—C9	111.58 (18)	C7—P1—Pd1	110.95 (6)
C11—C10—H10A	109.3	C1B—P1—Pd1	114.8 (4)
C9—C10—H10A	109.3	C13B—P1—Pd1	117.3 (4)
C11—C10—H10B	109.3	Cl1—Pd1—Cl1i	180.0
C9—C10—H10B	109.3	Cl1—Pd1—P1	89.296 (16)
H10A—C10—H10B	108.0	Cl1i—Pd1—P1	90.704 (16)
C10—C11—C12	112.03 (18)	Cl1—Pd1—P1i	90.704 (16)
C10—C11—H11A	109.2	Cl1i—Pd1—P1i	89.296 (16)
C12—C11—H11A	109.2	P1—Pd1—P1i	180.0
C10—C11—H11B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cl1	0.97	2.91	3.559 (2)	125
C5—H5···Cl1ii	0.93	2.94	3.619 (7)	131
C13—H13···Cl1i	0.98	2.68	3.254 (11)	118
C18—H18B···Cl1i	0.97	2.97	3.542 (13)	119
C15—H15A···Cl1iii	0.97	3.02	3.800 (8)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cl1	0.97	2.91	3.559 (2)	125
C5—H5⋯Cl1i	0.93	2.94	3.619 (7)	131
C13—H13⋯Cl1ii	0.98	2.68	3.254 (11)	118
C18—H18B⋯Cl1ii	0.97	2.97	3.542 (13)	119
C15—H15A⋯Cl1iii	0.97	3.02	3.800 (8)	139

Symmetry codes: (i) ; (ii) ; (iii) .