trans-Bis{1-[2-(2,6-diisopropyl­anilino)phenyl]-3-isopropyl­imidazolin-2-ylidenyl-κC2}diiodidopalladium(II) benzene disolvate

Daly, C.G.; Singh, K.; Cross, W.B.

doi:10.1107/S1600536811015431

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m668

doi:10.1107/S1600536811015431

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trans-Bis{1-[2-(2,6-diisopropylanilino)phenyl]-3-isopropylimidazolin-2-ylidenyl-κC²}diiodidopalladium(II) benzene disolvate

Christopher G. Daly,^a Kuldip Singh ^a and Warren B. Cross ^a ^*

^aDepartment of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, England
^*Correspondence e-mail: wbc2@le.ac.uk

(Received 17 April 2011; accepted 24 April 2011; online 7 May 2011)

In the title complex, [PdI₂(C₂₄H₃₁N₃)₂]·2C₆H₆, the Pd²⁺ ion is located on an inversion centre in a slightly distorted square-planar geometry. The angle between the I₂C₂ square plane and the mean plane of the N-heterocyclic carbene ring is 79.8 (2)°, with I—Pd—C—N torsion angles of −81.1 (6) and −78.2 (5)°. The Pd—carbene and Pd—I distances are 2.016 (6) and 2.5971 (10) Å, respectively.

Related literature

For a review of N-heterocyclic carbenes in late transition metal catalysis, see: Díez-González et al. (2009 ). For the synthesis of the pro-ligand and crystal structures of related complexes, see: Cross et al. (2011 ).

Experimental

Crystal data

[PdI₂(C₂₄H₃₁N₃)₂]·2C₆H₆
M_r = 1239.45
Triclinic, $[P \overline 1]$
a = 8.998 (4) Å
b = 12.000 (5) Å
c = 13.839 (6) Å
α = 81.572 (8)°
β = 78.819 (9)°
γ = 76.411 (8)°
V = 1417.0 (10) Å³
Z = 1
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 150 K
0.16 × 0.11 × 0.06 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.338, T_max = 0.831
11207 measured reflections
5500 independent reflections
3317 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.128
S = 0.88
5500 reflections
319 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −1.27 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2000 ); data reduction: SAINT and SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015431/pv2410sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015431/pv2410Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015431/pv2410Isup3.cdx

checkCIF report

Comment top

Bifunctional catalysis, in which an electrophilic metal and a nucleophilic ligand act together to activate a substrate, can enable reactions that are not possible using classical catalytic transformations that occur only at the metal centre. We are interested in catalysts in which an N-heterocyclic carbene ligand tethers a nucleophilic amido donor to the metal. Previously, we have reported tridentate amido-bis(NHC) (CNC) complexes of palladium and platinum, a bidentate amido-NHC (C,N-dipp) complex of palladium and a complex [trans-(C₂₄H₃₁N₃)PdI₂(py)], in which the amine-NHC ligand binds to Pd only through the carbene (Cross et al., 2011). In the synthesis of [trans-(C₂₄H₃₁N₃)PdI₂(py)], we isolated a single-crystal of the title complex.

The solid state structure of the title complex is shown in Fig. 1. Two NHC and two iodide ligands are coordinated to the square planar Pd, which is located at an inversion centre. The Pd-carbene distance of 2.016 (6) Å is ca 0.05 Å longer than in the corresponding complex [trans-(C₂₄H₃₁N₃)PdI₂(py)] (Cross et al., 2011), as a consequence of the strong trans- influence of the NHC ligand.

Related literature top

For a review of N-heterocyclic carbenes in late transition metal catalysis, see: Díez-González et al. (2009). For the synthesis of the pro-ligand and crystal structures of related complexes, see: Cross et al. (2011).

Experimental top

The title complex was an unexpected by-product in the synthesis of [trans-(C₂₄H₃₁N₃)PdI₂(py)] (Cross et al., 2011). Crystals of the title complex were grown by slow evaporation from benzene.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000) and SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex, with 50% probablity ellipsoids. Two molecules of benzene and H atoms except N—H have been omitted for clarity. Symmetry operation ⁱ = -x + 2, -y, -z.

trans-Bis{1-[2-(2,6-diisopropylanilino)phenyl]-3- isopropylimidazolin-2-ylidenyl-κC²}diiodidopalladium(II) benzene disolvate top

Crystal data top

[PdI₂(C₂₄H₃₁N₃)₂]·2C₆H₆	Z = 1
M_r = 1239.45	F(000) = 628
Triclinic, P1	D_x = 1.452 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.998 (4) Å	Cell parameters from 580 reflections
b = 12.000 (5) Å	θ = 2.4–23.4°
c = 13.839 (6) Å	µ = 1.46 mm⁻¹
α = 81.572 (8)°	T = 150 K
β = 78.819 (9)°	Block, yellow
γ = 76.411 (8)°	0.16 × 0.11 × 0.06 mm
V = 1417.0 (10) Å³

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	5500 independent reflections
Radiation source: fine-focus sealed tube	3317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
T_min = 0.338, T_max = 0.831	k = −14→14
11207 measured reflections	l = −17→17

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.035P)²] where P = (F_o² + 2F_c²)/3
5500 reflections	(Δ/σ)_max = 0.001
319 parameters	Δρ_max = 0.92 e Å⁻³
0 restraints	Δρ_min = −1.27 e Å⁻³

Crystal data top

[PdI₂(C₂₄H₃₁N₃)₂]·2C₆H₆	γ = 76.411 (8)°
M_r = 1239.45	V = 1417.0 (10) Å³
Triclinic, P1	Z = 1
a = 8.998 (4) Å	Mo Kα radiation
b = 12.000 (5) Å	µ = 1.46 mm⁻¹
c = 13.839 (6) Å	T = 150 K
α = 81.572 (8)°	0.16 × 0.11 × 0.06 mm
β = 78.819 (9)°

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	5500 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3317 reflections with I > 2σ(I)
T_min = 0.338, T_max = 0.831	R_int = 0.106
11207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 0.88	Δρ_max = 0.92 e Å⁻³
5500 reflections	Δρ_min = −1.27 e Å⁻³
319 parameters

Special details top

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
Pd1	1.0000	0.0000	0.0000	0.0245 (2)
I1	1.08790 (6)	0.17737 (4)	0.03915 (4)	0.03773 (18)
N1	0.7871 (6)	0.1906 (5)	0.3084 (4)	0.0291 (14)
H1	0.7552	0.2298	0.2546	0.035*
N2	0.7258 (6)	0.0747 (5)	0.1601 (4)	0.0245 (13)
N3	0.6700 (6)	0.1348 (5)	0.0142 (4)	0.0292 (14)
C1	0.7838 (7)	0.0734 (5)	0.0618 (5)	0.0262 (16)
C2	0.5403 (8)	0.1765 (6)	0.0799 (5)	0.0382 (19)
H2	0.4453	0.2227	0.0639	0.046*
C3	0.5740 (7)	0.1388 (6)	0.1722 (5)	0.0296 (17)
H3	0.5071	0.1533	0.2332	0.036*
C4	0.8000 (7)	0.0118 (6)	0.2392 (5)	0.0275 (16)
C5	0.8455 (8)	−0.1079 (6)	0.2430 (5)	0.0305 (17)
H5	0.8274	−0.1468	0.1927	0.037*
C6	0.9170 (8)	−0.1699 (6)	0.3198 (5)	0.0338 (18)
H6	0.9530	−0.2510	0.3204	0.041*
C7	0.9359 (8)	−0.1155 (6)	0.3943 (5)	0.0370 (19)
H7	0.9790	−0.1591	0.4491	0.044*
C8	0.8928 (8)	0.0033 (6)	0.3907 (5)	0.0319 (17)
H8	0.9082	0.0398	0.4433	0.038*
C9	0.8277 (7)	0.0710 (6)	0.3129 (5)	0.0265 (16)
C10	0.6882 (8)	0.1564 (6)	−0.0949 (5)	0.0354 (19)
H10	0.7875	0.1056	−0.1231	0.043*
C11	0.6985 (10)	0.2798 (7)	−0.1303 (6)	0.059 (3)
H11A	0.5979	0.3307	−0.1104	0.088*
H11B	0.7263	0.2885	−0.2026	0.088*
H11C	0.7778	0.3002	−0.1008	0.088*
C12	0.5553 (11)	0.1221 (9)	−0.1295 (6)	0.071 (3)
H12A	0.5662	0.0382	−0.1172	0.107*
H12B	0.5585	0.1460	−0.2006	0.107*
H12C	0.4561	0.1599	−0.0930	0.107*
C13	0.7948 (8)	0.2525 (6)	0.3867 (5)	0.0264 (16)
C14	0.6834 (8)	0.2513 (6)	0.4726 (5)	0.0293 (17)
C15	0.6914 (8)	0.3156 (6)	0.5452 (5)	0.0370 (19)
H15	0.6181	0.3148	0.6047	0.044*
C16	0.8014 (9)	0.3811 (6)	0.5353 (6)	0.043 (2)
H16	0.8035	0.4250	0.5866	0.052*
C17	0.9087 (9)	0.3814 (6)	0.4490 (6)	0.041 (2)
H17	0.9838	0.4273	0.4415	0.049*
C18	0.9109 (8)	0.3185 (6)	0.3745 (5)	0.0308 (17)
C19	0.5504 (9)	0.1905 (6)	0.4850 (5)	0.039 (2)
H19	0.5708	0.1432	0.4282	0.047*
C20	0.5396 (10)	0.1076 (7)	0.5800 (6)	0.060 (3)
H20A	0.6394	0.0533	0.5819	0.090*
H20B	0.4587	0.0649	0.5814	0.090*
H20C	0.5139	0.1514	0.6376	0.090*
C21	0.3993 (9)	0.2773 (7)	0.4780 (6)	0.057 (2)
H21A	0.3738	0.3240	0.5338	0.086*
H21B	0.3162	0.2366	0.4799	0.086*
H21C	0.4103	0.3276	0.4156	0.086*
C22	1.0365 (8)	0.3122 (7)	0.2834 (6)	0.042 (2)
H22	0.9868	0.3124	0.2247	0.051*
C23	1.1199 (9)	0.4138 (7)	0.2635 (6)	0.057 (2)
H23A	1.0434	0.4866	0.2581	0.086*
H23B	1.1940	0.4070	0.2015	0.086*
H23C	1.1752	0.4124	0.3182	0.086*
C24	1.1573 (9)	0.1988 (7)	0.2928 (6)	0.053 (2)
H24A	1.2033	0.1944	0.3523	0.079*
H24B	1.2388	0.1961	0.2342	0.079*
H24C	1.1071	0.1336	0.2978	0.079*
C25	0.5767 (11)	0.4395 (7)	0.2054 (8)	0.060 (3)
H25	0.5044	0.3906	0.2232	0.072*
C26	0.6599 (13)	0.4465 (9)	0.1094 (8)	0.078 (3)
H26	0.6473	0.4008	0.0623	0.093*
C27	0.7615 (12)	0.5211 (9)	0.0835 (8)	0.079 (3)
H27	0.8176	0.5285	0.0181	0.095*
C28	0.7792 (12)	0.5832 (8)	0.1533 (9)	0.071 (3)
H28	0.8497	0.6335	0.1365	0.085*
C29	0.6973 (12)	0.5746 (8)	0.2475 (8)	0.071 (3)
H29	0.7099	0.6198	0.2950	0.085*
C30	0.5984 (10)	0.5019 (7)	0.2729 (7)	0.056 (3)
H30	0.5439	0.4948	0.3388	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0217 (4)	0.0279 (4)	0.0209 (4)	−0.0004 (3)	−0.0016 (3)	−0.0040 (3)
I1	0.0378 (3)	0.0405 (3)	0.0365 (3)	−0.0119 (2)	0.0001 (2)	−0.0124 (2)
N1	0.036 (4)	0.024 (3)	0.025 (3)	0.003 (3)	−0.016 (3)	0.003 (3)
N2	0.019 (3)	0.035 (3)	0.018 (3)	−0.002 (3)	−0.002 (2)	−0.008 (3)
N3	0.021 (3)	0.033 (3)	0.030 (4)	0.005 (3)	−0.009 (3)	−0.003 (3)
C1	0.026 (4)	0.025 (4)	0.028 (4)	−0.006 (3)	−0.003 (3)	−0.004 (3)
C2	0.024 (4)	0.049 (5)	0.037 (5)	0.003 (4)	−0.004 (4)	−0.008 (4)
C3	0.019 (4)	0.041 (4)	0.026 (4)	0.000 (3)	−0.002 (3)	−0.003 (3)
C4	0.020 (4)	0.040 (4)	0.020 (4)	−0.007 (3)	−0.002 (3)	0.003 (3)
C5	0.034 (4)	0.035 (4)	0.027 (4)	−0.013 (3)	−0.005 (3)	−0.006 (3)
C6	0.035 (4)	0.029 (4)	0.032 (5)	−0.003 (3)	0.002 (4)	−0.005 (4)
C7	0.044 (5)	0.036 (5)	0.029 (4)	−0.006 (4)	−0.010 (4)	0.003 (4)
C8	0.031 (4)	0.035 (4)	0.029 (4)	0.000 (3)	−0.009 (3)	−0.011 (4)
C9	0.026 (4)	0.029 (4)	0.020 (4)	−0.002 (3)	0.002 (3)	−0.001 (3)
C10	0.040 (5)	0.045 (5)	0.013 (4)	0.006 (4)	−0.005 (3)	0.000 (3)
C11	0.074 (7)	0.061 (6)	0.033 (5)	0.004 (5)	−0.013 (5)	0.001 (4)
C12	0.086 (8)	0.103 (8)	0.033 (5)	−0.019 (6)	−0.024 (5)	−0.015 (5)
C13	0.029 (4)	0.023 (4)	0.029 (4)	−0.002 (3)	−0.015 (3)	−0.005 (3)
C14	0.028 (4)	0.029 (4)	0.032 (4)	−0.003 (3)	−0.002 (3)	−0.011 (3)
C15	0.039 (5)	0.037 (5)	0.032 (5)	−0.003 (4)	0.000 (4)	−0.009 (4)
C16	0.055 (5)	0.027 (4)	0.045 (5)	0.002 (4)	−0.008 (4)	−0.015 (4)
C17	0.035 (5)	0.034 (4)	0.052 (6)	−0.003 (4)	−0.009 (4)	−0.005 (4)
C18	0.032 (4)	0.032 (4)	0.026 (4)	0.002 (3)	−0.011 (3)	−0.002 (3)
C19	0.052 (5)	0.047 (5)	0.020 (4)	−0.015 (4)	−0.002 (4)	−0.012 (4)
C20	0.063 (6)	0.070 (7)	0.047 (6)	−0.026 (5)	−0.003 (5)	0.004 (5)
C21	0.042 (5)	0.075 (7)	0.057 (6)	−0.013 (5)	−0.016 (5)	−0.003 (5)
C22	0.036 (5)	0.062 (6)	0.034 (5)	−0.017 (4)	−0.011 (4)	−0.003 (4)
C23	0.047 (5)	0.065 (6)	0.062 (6)	−0.024 (5)	−0.005 (5)	0.001 (5)
C24	0.031 (5)	0.070 (6)	0.051 (6)	0.004 (4)	−0.001 (4)	−0.020 (5)
C25	0.063 (6)	0.041 (6)	0.069 (7)	0.004 (5)	−0.014 (6)	−0.002 (5)
C26	0.094 (9)	0.064 (7)	0.075 (8)	−0.001 (6)	−0.019 (7)	−0.025 (6)
C27	0.075 (8)	0.077 (8)	0.065 (8)	−0.003 (6)	0.016 (6)	0.000 (6)
C28	0.078 (8)	0.053 (7)	0.082 (8)	−0.023 (6)	−0.019 (7)	0.018 (6)
C29	0.084 (8)	0.050 (6)	0.073 (8)	0.000 (6)	−0.023 (6)	0.002 (6)
C30	0.058 (6)	0.032 (5)	0.062 (7)	0.005 (4)	0.002 (5)	0.002 (5)

Geometric parameters (Å, º) top

Pd1—C1	2.016 (6)	C14—C19	1.513 (9)
Pd1—C1ⁱ	2.016 (6)	C15—C16	1.377 (9)
Pd1—I1ⁱ	2.5971 (10)	C15—H15	0.9500
Pd1—I1	2.5971 (10)	C16—C17	1.382 (10)
N1—C9	1.390 (8)	C16—H16	0.9500
N1—C13	1.421 (8)	C17—C18	1.359 (9)
N1—H1	0.8800	C17—H17	0.9500
N2—C1	1.359 (8)	C18—C22	1.518 (9)
N2—C3	1.393 (8)	C19—C21	1.517 (10)
N2—C4	1.421 (8)	C19—C20	1.530 (10)
N3—C1	1.338 (8)	C19—H19	1.0000
N3—C2	1.373 (8)	C20—H20A	0.9800
N3—C10	1.478 (8)	C20—H20B	0.9800
C2—C3	1.359 (9)	C20—H20C	0.9800
C2—H2	0.9500	C21—H21A	0.9800
C3—H3	0.9500	C21—H21B	0.9800
C4—C5	1.395 (9)	C21—H21C	0.9800
C4—C9	1.414 (9)	C22—C24	1.536 (10)
C5—C6	1.380 (9)	C22—C23	1.542 (10)
C5—H5	0.9500	C22—H22	1.0000
C6—C7	1.355 (9)	C23—H23A	0.9800
C6—H6	0.9500	C23—H23B	0.9800
C7—C8	1.382 (9)	C23—H23C	0.9800
C7—H7	0.9500	C24—H24A	0.9800
C8—C9	1.389 (9)	C24—H24B	0.9800
C8—H8	0.9500	C24—H24C	0.9800
C10—C11	1.508 (10)	C25—C30	1.348 (11)
C10—C12	1.531 (10)	C25—C26	1.394 (12)
C10—H10	1.0000	C25—H25	0.9500
C11—H11A	0.9800	C26—C27	1.389 (13)
C11—H11B	0.9800	C26—H26	0.9500
C11—H11C	0.9800	C27—C28	1.355 (13)
C12—H12A	0.9800	C27—H27	0.9500
C12—H12B	0.9800	C28—C29	1.371 (12)
C12—H12C	0.9800	C28—H28	0.9500
C13—C14	1.399 (9)	C29—C30	1.353 (12)
C13—C18	1.425 (9)	C29—H29	0.9500
C14—C15	1.375 (9)	C30—H30	0.9500

C1—Pd1—C1ⁱ	180.0 (5)	C14—C15—C16	122.7 (7)
C1—Pd1—I1ⁱ	92.78 (18)	C14—C15—H15	118.7
C1ⁱ—Pd1—I1ⁱ	87.22 (18)	C16—C15—H15	118.7
C1—Pd1—I1	87.22 (18)	C15—C16—C17	118.5 (7)
C1ⁱ—Pd1—I1	92.78 (18)	C15—C16—H16	120.7
I1ⁱ—Pd1—I1	180.00 (2)	C17—C16—H16	120.7
C9—N1—C13	123.0 (6)	C18—C17—C16	122.6 (7)
C9—N1—H1	118.5	C18—C17—H17	118.7
C13—N1—H1	118.5	C16—C17—H17	118.7
C1—N2—C3	109.4 (5)	C17—C18—C13	117.5 (7)
C1—N2—C4	126.2 (5)	C17—C18—C22	122.2 (7)
C3—N2—C4	124.0 (5)	C13—C18—C22	120.2 (6)
C1—N3—C2	111.1 (6)	C14—C19—C21	110.5 (6)
C1—N3—C10	122.9 (6)	C14—C19—C20	112.6 (6)
C2—N3—C10	125.9 (6)	C21—C19—C20	112.0 (7)
N3—C1—N2	106.0 (6)	C14—C19—H19	107.1
N3—C1—Pd1	126.8 (5)	C21—C19—H19	107.1
N2—C1—Pd1	127.1 (5)	C20—C19—H19	107.1
C3—C2—N3	106.8 (6)	C19—C20—H20A	109.5
C3—C2—H2	126.6	C19—C20—H20B	109.5
N3—C2—H2	126.6	H20A—C20—H20B	109.5
C2—C3—N2	106.7 (6)	C19—C20—H20C	109.5
C2—C3—H3	126.7	H20A—C20—H20C	109.5
N2—C3—H3	126.7	H20B—C20—H20C	109.5
C5—C4—C9	120.7 (6)	C19—C21—H21A	109.5
C5—C4—N2	119.4 (6)	C19—C21—H21B	109.5
C9—C4—N2	119.9 (6)	H21A—C21—H21B	109.5
C6—C5—C4	119.9 (7)	C19—C21—H21C	109.5
C6—C5—H5	120.0	H21A—C21—H21C	109.5
C4—C5—H5	120.0	H21B—C21—H21C	109.5
C7—C6—C5	120.2 (7)	C18—C22—C24	110.1 (6)
C7—C6—H6	119.9	C18—C22—C23	113.9 (7)
C5—C6—H6	119.9	C24—C22—C23	108.9 (6)
C6—C7—C8	120.2 (7)	C18—C22—H22	107.9
C6—C7—H7	119.9	C24—C22—H22	107.9
C8—C7—H7	119.9	C23—C22—H22	107.9
C7—C8—C9	122.3 (7)	C22—C23—H23A	109.5
C7—C8—H8	118.9	C22—C23—H23B	109.5
C9—C8—H8	118.9	H23A—C23—H23B	109.5
C8—C9—N1	122.3 (6)	C22—C23—H23C	109.5
C8—C9—C4	116.5 (6)	H23A—C23—H23C	109.5
N1—C9—C4	121.3 (6)	H23B—C23—H23C	109.5
N3—C10—C11	111.4 (6)	C22—C24—H24A	109.5
N3—C10—C12	109.1 (6)	C22—C24—H24B	109.5
C11—C10—C12	112.4 (7)	H24A—C24—H24B	109.5
N3—C10—H10	107.9	C22—C24—H24C	109.5
C11—C10—H10	107.9	H24A—C24—H24C	109.5
C12—C10—H10	107.9	H24B—C24—H24C	109.5
C10—C11—H11A	109.5	C30—C25—C26	120.2 (10)
C10—C11—H11B	109.5	C30—C25—H25	119.9
H11A—C11—H11B	109.5	C26—C25—H25	119.9
C10—C11—H11C	109.5	C27—C26—C25	119.2 (10)
H11A—C11—H11C	109.5	C27—C26—H26	120.4
H11B—C11—H11C	109.5	C25—C26—H26	120.4
C10—C12—H12A	109.5	C28—C27—C26	118.8 (10)
C10—C12—H12B	109.5	C28—C27—H27	120.6
H12A—C12—H12B	109.5	C26—C27—H27	120.6
C10—C12—H12C	109.5	C27—C28—C29	121.2 (10)
H12A—C12—H12C	109.5	C27—C28—H28	119.4
H12B—C12—H12C	109.5	C29—C28—H28	119.4
C14—C13—N1	119.1 (6)	C30—C29—C28	120.1 (10)
C14—C13—C18	121.4 (6)	C30—C29—H29	120.0
N1—C13—C18	119.5 (6)	C28—C29—H29	120.0
C15—C14—C13	117.3 (6)	C25—C30—C29	120.4 (9)
C15—C14—C19	119.5 (6)	C25—C30—H30	119.8
C13—C14—C19	123.0 (6)	C29—C30—H30	119.8

C2—N3—C1—N2	0.5 (8)	C1—N3—C10—C11	−107.3 (8)
C10—N3—C1—N2	178.5 (6)	C2—N3—C10—C11	70.3 (9)
C2—N3—C1—Pd1	−177.1 (5)	C1—N3—C10—C12	128.0 (7)
C10—N3—C1—Pd1	0.9 (9)	C2—N3—C10—C12	−54.3 (9)
C3—N2—C1—N3	−0.4 (7)	C9—N1—C13—C14	−73.6 (8)
C4—N2—C1—N3	173.8 (6)	C9—N1—C13—C18	109.2 (7)
C3—N2—C1—Pd1	177.2 (5)	N1—C13—C14—C15	−177.7 (6)
C4—N2—C1—Pd1	−8.6 (9)	C18—C13—C14—C15	−0.6 (10)
I1ⁱ—Pd1—C1—N3	−81.1 (6)	N1—C13—C14—C19	−2.4 (10)
I1—Pd1—C1—N3	98.9 (6)	C18—C13—C14—C19	174.7 (7)
I1ⁱ—Pd1—C1—N2	101.8 (5)	C13—C14—C15—C16	1.1 (11)
I1—Pd1—C1—N2	−78.2 (5)	C19—C14—C15—C16	−174.3 (7)
C1—N3—C2—C3	−0.5 (8)	C14—C15—C16—C17	−0.5 (12)
C10—N3—C2—C3	−178.4 (6)	C15—C16—C17—C18	−0.9 (12)
N3—C2—C3—N2	0.3 (8)	C16—C17—C18—C13	1.4 (11)
C1—N2—C3—C2	0.0 (8)	C16—C17—C18—C22	−175.2 (7)
C4—N2—C3—C2	−174.2 (6)	C14—C13—C18—C17	−0.6 (10)
C1—N2—C4—C5	−57.2 (9)	N1—C13—C18—C17	176.4 (6)
C3—N2—C4—C5	116.1 (7)	C14—C13—C18—C22	176.0 (7)
C1—N2—C4—C9	122.4 (7)	N1—C13—C18—C22	−6.9 (10)
C3—N2—C4—C9	−64.3 (8)	C15—C14—C19—C21	68.8 (9)
C9—C4—C5—C6	0.7 (10)	C13—C14—C19—C21	−106.4 (8)
N2—C4—C5—C6	−179.7 (6)	C15—C14—C19—C20	−57.4 (9)
C4—C5—C6—C7	3.4 (10)	C13—C14—C19—C20	127.4 (7)
C5—C6—C7—C8	−4.1 (10)	C17—C18—C22—C24	100.7 (8)
C6—C7—C8—C9	0.7 (11)	C13—C18—C22—C24	−75.9 (8)
C7—C8—C9—N1	−178.7 (6)	C17—C18—C22—C23	−22.0 (10)
C7—C8—C9—C4	3.2 (10)	C13—C18—C22—C23	161.5 (7)
C13—N1—C9—C8	−6.2 (10)	C30—C25—C26—C27	−2.0 (14)
C13—N1—C9—C4	171.8 (6)	C25—C26—C27—C28	1.4 (16)
C5—C4—C9—C8	−3.9 (9)	C26—C27—C28—C29	−1.0 (16)
N2—C4—C9—C8	176.5 (6)	C27—C28—C29—C30	1.1 (15)
C5—C4—C9—N1	178.0 (6)	C26—C25—C30—C29	2.1 (14)
N2—C4—C9—N1	−1.6 (9)	C28—C29—C30—C25	−1.6 (14)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[PdI₂(C₂₄H₃₁N₃)₂]·2C₆H₆
M_r	1239.45
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.998 (4), 12.000 (5), 13.839 (6)
α, β, γ (°)	81.572 (8), 78.819 (9), 76.411 (8)
V (Å³)	1417.0 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.16 × 0.11 × 0.06

Data collection
Diffractometer	Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.338, 0.831
No. of measured, independent and observed [I > 2σ(I)] reflections	11207, 5500, 3317
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.128, 0.88
No. of reflections	5500
No. of parameters	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −1.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2000) and SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The University of Leicester is thanked for a graduate studentship to CGD.

References

Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cross, W. B., Daly, C. G., Ackerman, R. L., George, I. R. & Singh, K. (2011). Dalton Trans. 40, 495–505. Web of Science CrossRef CAS PubMed Google Scholar
Díez-González, S., Marion, N. & Nolan, S. P. N. (2009). Chem. Rev. pp 3612–3677. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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