Crystal structure of [N,N′-bis­(4-methyl­phen­yl)-1,2-di­phenyl­ethane-1,2-di­imine-κ2N,N′]di­chlorido­palladium(II) methanol monosolvate

Peñaloza, A.; Fronczek, F.R.; Isovitsch, R.

doi:10.1107/S2056989015014851

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 9| September 2015| Pages m164-m165

https://doi.org/10.1107/S2056989015014851

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Crystal structure of [N,N′-bis(4-methylphenyl)-1,2-diphenylethane-1,2-diimine-κ²N,N′]dichloridopalladium(II) methanol monosolvate

Alfredo Peñaloza,^a Frank R. Fronczek ^b and Ralph Isovitsch ^a ^*

^a13406 Philadelphia Street, Whittier College, Department of Chemistry, Whittier College, Whittier, CA 90601, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
^*Correspondence e-mail: risovitsch@whittier.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 July 2015; accepted 7 August 2015; online 15 August 2015)

The title compound, [PdCl₂(C₂₈H₂₄N₂)]·CH₃OH, was prepared from the reaction of PdCl₂(DMSO)₂ (DMSO is dimethyl sulfoxide) and N,N′-bis(4-methylphenyl)-1,2-diphenylethane-1,2-diimine in methanol. The chelating diimine core of the title compound deviates slightly from planarity, with an N—C—C—N torsion angle of 5.3 (3)°. Delocalization in the diimine core is indicated by N—C and C—C bonds that are, respectively, longer and shorter than those found in related nonchelating diimines. The distorted square-planar coordination environment around the Pd^II atom is manifested as bond angles that are smaller and larger than 90°, and palladacycle torsion angles of −173.22 (16) and 167.06 (16)°. These deviations are attributed to the small bite angle of 79.13 (8)° of the diimine chelate. The crystal packing exhibits weak intermolecular hydrogen-bonding interactions involving aromatic H atoms, Cl atoms and intercalated methanol solvent molecules, defining layers parallel to (010).

Keywords: crystal structure; palladium(II) dichlorido diimine complex; polymerization catalyst.

CCDC reference: 1417572

1. Related literature

Palladium(II) diimiine complexes have been widely used as polymerization catalysts for α-olefins (Johnson et al., 1995 ; Popeney & Guan, 2005 ) and are prepared easily by the reaction of PdCl₂(DMSO)₂ with the diimine of choice (Kubota et al., 2013 ; Ettedgui & Neumann, 2009 ; Price et al., 1972 ). For structural information about related palladium(II) diimine complexes, see: Kubota et al. (2013); Comerlato et al. (2001 ); Dyakonenko et al. (2015 ). For structures of other diimines, see: Wang et al. (2012 ); Zhao et al. (2015 ).

2. Experimental

2.1. Crystal data

[PdCl₂(C₂₈H₂₄N₂)]·CH₄O
M_r = 597.83
Triclinic, $[P \overline 1]$
a = 8.8213 (3) Å
b = 12.3364 (3) Å
c = 12.7697 (4) Å
α = 108.992 (2)°
β = 93.900 (3)°
γ = 92.457 (3)°
V = 1307.83 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 90 K
0.18 × 0.10 × 0.06 mm

2.2. Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.831, T_max = 0.946
12258 measured reflections
5965 independent reflections
5026 reflections with I > 2σ(I)
R_int = 0.032

2.3. Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.066
S = 1.02
5965 reflections
322 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H10H⋯Cl2	0.83 (2)	2.36 (2)	3.161 (2)	163 (3)
C17—H17⋯Cl2ⁱ	0.95	2.80	3.708 (3)	161
C21—H21⋯O1ⁱⁱ	0.95	2.48	3.275 (3)	141
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1417572

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015014851/wm5193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014851/wm5193Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015014851/wm5193sup3.pdf

checkCIF report

Synthesis and crystallization top

0.086 g (0.257 mmol, 1 eq.) of PdCl₂(DMSO)₂ and 0.100 g (0.257 mmol, 1 eq.) of N,N'-di(4-methylphenyl)-1,2-diphenylethane-1,2-diimine were combined with 10 ml of methanol and stirred for 1.5 hours at room temperature. The orange precipitate that formed was collected via vacuum filtration, washed well with water and then air-dried giving 0.0363 g (25%) of the title compound. Slow evaporation of the reaction mixture gave X-ray quality crystals of the title compound. MP: > 532 K. IR (KCl): 3135, 2922, 1514 cm^-1. UV-Vis (λ nm (ε)): 242 (41,200), 264 (34,800), 317 (17,800). TLC (alumina, ethanol): R_f = 0.59.

Refinement top

H atoms were placed in idealized positions, guided by difference maps, with C—H bond lengths in the range 0.95-0.98 Å, with U_iso(H) = 1.2U_eq(C) of the attached atom (1.5 for methyl), and thereafter treated as riding. A torsional parameter was refined for each methyl group. The H atom of the methanol solvent molecule was refined with O—H = 0.85 Å and U_iso(H) = 1.5U_eq(O).

Related literature top

Palladium(II) diimiine complexes have been widely used as polymerization catalysts for α-olefins (Johnson et al., 1995; Popeney & Guan, 2005) and are easily prepared by the reaction of PdCl₂(DMSO)₂ with the diimine of choice (Kubota et al., 2013; Ettedgui & Neumann, 2009; Price et al., 1972). For structural information about related palladium(II) diimine complexes, see: Kubota et al. (2013); Comerlato et al. (2001); Dyakonenko et al. (2015). For structures of other diimines, see: Wang et al. (2012); Zhao et al. (2015).

Structure description top

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular components of the title compound. Displacement ellipsoids are represented at the 50% probability level.
	Fig. 2. Crystal packing in the title compound, with intermolecular hydrogen bonding emphasized as dashed lines.
	Fig. 3. Crystal packing in the title compound as viewed along [100].

[N,N'-Bis(4-methylphenyl)-1,2-diphenylethane-1,2-diimine-κ²N,N']dichloridopalladium(II) methanol monosolvate top

Crystal data top

[PdCl₂(C₂₈H₂₄N₂)]·CH₄O	Z = 2
M_r = 597.83	F(000) = 608
Triclinic, P1	D_x = 1.518 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8213 (3) Å	Cell parameters from 4900 reflections
b = 12.3364 (3) Å	θ = 2.8–27.5°
c = 12.7697 (4) Å	µ = 0.94 mm⁻¹
α = 108.992 (2)°	T = 90 K
β = 93.900 (3)°	Plate, orange
γ = 92.457 (3)°	0.18 × 0.10 × 0.06 mm
V = 1307.83 (7) Å³

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	5965 independent reflections
Radiation source: fine-focus sealed tube	5026 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −11→11
T_min = 0.831, T_max = 0.946	k = −16→16
12258 measured reflections	l = −16→16

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0243P)² + 0.2447P] where P = (F_o² + 2F_c²)/3
5965 reflections	(Δ/σ)_max = 0.002
322 parameters	Δρ_max = 0.57 e Å⁻³
1 restraint	Δρ_min = −0.64 e Å⁻³

Crystal data top

[PdCl₂(C₂₈H₂₄N₂)]·CH₄O	γ = 92.457 (3)°
M_r = 597.83	V = 1307.83 (7) Å³
Triclinic, P1	Z = 2
a = 8.8213 (3) Å	Mo Kα radiation
b = 12.3364 (3) Å	µ = 0.94 mm⁻¹
c = 12.7697 (4) Å	T = 90 K
α = 108.992 (2)°	0.18 × 0.10 × 0.06 mm
β = 93.900 (3)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	5965 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	5026 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.946	R_int = 0.032
12258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	1 restraint
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.57 e Å⁻³
5965 reflections	Δρ_min = −0.64 e Å⁻³
322 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	0.72678 (2)	0.502582 (15)	0.508729 (15)	0.00896 (6)
Cl1	0.66581 (7)	0.51705 (5)	0.33726 (5)	0.01389 (13)
Cl2	0.78558 (7)	0.31784 (5)	0.42450 (5)	0.01609 (14)
N1	0.7550 (2)	0.49790 (16)	0.66557 (16)	0.0092 (4)
N2	0.6911 (2)	0.66555 (16)	0.59660 (16)	0.0102 (4)
C1	0.7157 (3)	0.5882 (2)	0.7421 (2)	0.0109 (5)
C2	0.6855 (3)	0.6871 (2)	0.7029 (2)	0.0114 (5)
C3	0.8034 (3)	0.39982 (19)	0.69323 (19)	0.0110 (5)
C4	0.9500 (3)	0.3682 (2)	0.67176 (19)	0.0125 (5)
H4	1.0122	0.4074	0.6357	0.015*
C5	1.0047 (3)	0.2789 (2)	0.7035 (2)	0.0151 (5)
H5	1.1058	0.2580	0.6900	0.018*
C6	0.9146 (3)	0.2192 (2)	0.7545 (2)	0.0150 (5)
C7	0.7650 (3)	0.2482 (2)	0.7692 (2)	0.0163 (6)
H7	0.7002	0.2054	0.8002	0.020*
C8	0.7082 (3)	0.3385 (2)	0.7394 (2)	0.0130 (5)
H8	0.6060	0.3578	0.7505	0.016*
C9	0.9798 (3)	0.1291 (2)	0.7979 (2)	0.0226 (6)
H9A	1.0674	0.0985	0.7573	0.034*
H9B	0.9018	0.0667	0.7874	0.034*
H9C	1.0126	0.1639	0.8773	0.034*
C10	0.7048 (3)	0.59987 (19)	0.8604 (2)	0.0112 (5)
C11	0.8257 (3)	0.5791 (2)	0.9252 (2)	0.0142 (5)
H11	0.9185	0.5560	0.8937	0.017*
C12	0.8109 (3)	0.5920 (2)	1.0360 (2)	0.0186 (6)
H12	0.8943	0.5789	1.0805	0.022*
C13	0.6756 (3)	0.6238 (2)	1.0820 (2)	0.0212 (6)
H13	0.6658	0.6318	1.1577	0.025*
C14	0.5547 (3)	0.6441 (2)	1.0180 (2)	0.0184 (6)
H14	0.4616	0.6654	1.0496	0.022*
C15	0.5689 (3)	0.6334 (2)	0.9075 (2)	0.0155 (5)
H15	0.4862	0.6488	0.8641	0.019*
C16	0.6638 (3)	0.8028 (2)	0.78122 (19)	0.0117 (5)
C17	0.5369 (3)	0.8595 (2)	0.7631 (2)	0.0158 (5)
H17	0.4630	0.8228	0.7029	0.019*
C18	0.5185 (3)	0.9697 (2)	0.8332 (2)	0.0192 (6)
H18	0.4316	1.0084	0.8210	0.023*
C19	0.6264 (3)	1.0236 (2)	0.9210 (2)	0.0211 (6)
H19	0.6145	1.0997	0.9681	0.025*
C20	0.7514 (3)	0.9665 (2)	0.9400 (2)	0.0192 (6)
H20	0.8244	1.0031	1.0010	0.023*
C21	0.7709 (3)	0.8564 (2)	0.8709 (2)	0.0155 (5)
H21	0.8568	0.8175	0.8844	0.019*
C22	0.6995 (3)	0.75880 (19)	0.55233 (19)	0.0107 (5)
C23	0.5828 (3)	0.7719 (2)	0.4801 (2)	0.0130 (5)
H23	0.4960	0.7188	0.4581	0.016*
C24	0.5944 (3)	0.8638 (2)	0.4402 (2)	0.0141 (5)
H24	0.5146	0.8734	0.3908	0.017*
C25	0.7211 (3)	0.9422 (2)	0.4715 (2)	0.0136 (5)
C26	0.8371 (3)	0.9256 (2)	0.5424 (2)	0.0149 (5)
H26	0.9243	0.9783	0.5640	0.018*
C27	0.8288 (3)	0.8339 (2)	0.5825 (2)	0.0135 (5)
H27	0.9101	0.8227	0.6298	0.016*
C28	0.7325 (3)	1.0438 (2)	0.4304 (2)	0.0200 (6)
H28A	0.8004	1.0280	0.3704	0.030*
H28B	0.7734	1.1122	0.4917	0.030*
H28C	0.6311	1.0572	0.4026	0.030*
O1	0.9588 (2)	0.31675 (18)	0.21549 (16)	0.0275 (5)
H10H	0.916 (4)	0.333 (3)	0.274 (2)	0.041*
C29	0.8406 (3)	0.2883 (3)	0.1302 (2)	0.0322 (8)
H29A	0.7635	0.2362	0.1441	0.048*
H29B	0.8815	0.2505	0.0589	0.048*
H29C	0.7942	0.3584	0.1281	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01082 (10)	0.00890 (9)	0.00697 (10)	−0.00045 (7)	0.00080 (7)	0.00251 (7)
Cl1	0.0166 (3)	0.0163 (3)	0.0086 (3)	0.0014 (2)	−0.0004 (2)	0.0042 (2)
Cl2	0.0252 (4)	0.0101 (3)	0.0123 (3)	0.0019 (2)	0.0020 (3)	0.0027 (2)
N1	0.0083 (10)	0.0103 (10)	0.0096 (10)	−0.0003 (8)	0.0001 (8)	0.0045 (8)
N2	0.0105 (10)	0.0094 (10)	0.0110 (10)	0.0014 (8)	0.0002 (8)	0.0037 (8)
C1	0.0070 (12)	0.0140 (12)	0.0120 (12)	−0.0020 (9)	−0.0010 (9)	0.0055 (10)
C2	0.0091 (12)	0.0126 (12)	0.0123 (12)	0.0010 (9)	0.0012 (9)	0.0037 (10)
C3	0.0153 (13)	0.0085 (11)	0.0076 (12)	0.0006 (9)	−0.0016 (9)	0.0010 (10)
C4	0.0135 (13)	0.0141 (12)	0.0084 (12)	0.0003 (10)	0.0008 (10)	0.0018 (10)
C5	0.0147 (13)	0.0171 (13)	0.0103 (13)	0.0046 (10)	0.0010 (10)	−0.0001 (10)
C6	0.0247 (15)	0.0090 (12)	0.0095 (12)	0.0046 (10)	−0.0028 (10)	0.0012 (10)
C7	0.0227 (15)	0.0134 (13)	0.0132 (13)	−0.0013 (11)	0.0033 (11)	0.0049 (11)
C8	0.0138 (13)	0.0131 (12)	0.0106 (12)	−0.0003 (10)	0.0001 (10)	0.0021 (10)
C9	0.0314 (16)	0.0203 (14)	0.0182 (15)	0.0105 (12)	0.0013 (12)	0.0083 (12)
C10	0.0138 (13)	0.0089 (12)	0.0107 (12)	−0.0005 (9)	0.0001 (10)	0.0034 (10)
C11	0.0149 (13)	0.0133 (12)	0.0146 (13)	0.0036 (10)	0.0001 (10)	0.0051 (10)
C12	0.0244 (15)	0.0172 (14)	0.0121 (13)	−0.0012 (11)	−0.0066 (11)	0.0038 (11)
C13	0.0306 (16)	0.0221 (14)	0.0113 (13)	−0.0031 (12)	0.0034 (12)	0.0066 (11)
C14	0.0190 (14)	0.0204 (14)	0.0150 (14)	−0.0001 (11)	0.0052 (11)	0.0041 (11)
C15	0.0183 (14)	0.0142 (13)	0.0142 (13)	0.0002 (10)	−0.0001 (10)	0.0053 (11)
C16	0.0159 (13)	0.0110 (12)	0.0087 (12)	0.0009 (10)	0.0025 (10)	0.0036 (10)
C17	0.0188 (14)	0.0179 (13)	0.0114 (13)	0.0026 (10)	0.0016 (10)	0.0057 (11)
C18	0.0222 (15)	0.0187 (14)	0.0194 (14)	0.0086 (11)	0.0055 (11)	0.0084 (12)
C19	0.0324 (17)	0.0136 (13)	0.0165 (14)	0.0031 (12)	0.0103 (12)	0.0023 (11)
C20	0.0252 (15)	0.0165 (13)	0.0124 (13)	−0.0042 (11)	0.0004 (11)	0.0010 (11)
C21	0.0182 (14)	0.0166 (13)	0.0127 (13)	0.0018 (10)	0.0011 (10)	0.0062 (11)
C22	0.0162 (13)	0.0079 (11)	0.0085 (12)	0.0031 (9)	0.0045 (10)	0.0023 (9)
C23	0.0132 (13)	0.0139 (12)	0.0105 (12)	0.0011 (10)	0.0014 (10)	0.0021 (10)
C24	0.0138 (13)	0.0173 (13)	0.0119 (13)	0.0056 (10)	0.0008 (10)	0.0052 (11)
C25	0.0179 (13)	0.0119 (12)	0.0125 (13)	0.0044 (10)	0.0063 (10)	0.0046 (10)
C26	0.0148 (13)	0.0138 (13)	0.0170 (14)	−0.0003 (10)	0.0031 (10)	0.0063 (11)
C27	0.0138 (13)	0.0178 (13)	0.0093 (12)	0.0002 (10)	−0.0004 (10)	0.0053 (10)
C28	0.0232 (15)	0.0182 (14)	0.0243 (15)	0.0064 (11)	0.0077 (12)	0.0129 (12)
O1	0.0199 (11)	0.0366 (12)	0.0214 (11)	0.0001 (9)	0.0066 (9)	0.0027 (10)
C29	0.0231 (17)	0.0367 (18)	0.0260 (17)	−0.0004 (13)	0.0067 (13)	−0.0050 (14)

Geometric parameters (Å, º) top

Pd1—N2	2.0086 (19)	C14—C15	1.388 (3)
Pd1—N1	2.0211 (19)	C14—H14	0.9500
Pd1—Cl2	2.2807 (6)	C15—H15	0.9500
Pd1—Cl1	2.2842 (6)	C16—C17	1.390 (4)
N1—C1	1.299 (3)	C16—C21	1.396 (3)
N1—C3	1.440 (3)	C17—C18	1.386 (4)
N2—C2	1.300 (3)	C17—H17	0.9500
N2—C22	1.439 (3)	C18—C19	1.386 (4)
C1—C10	1.480 (3)	C18—H18	0.9500
C1—C2	1.489 (3)	C19—C20	1.383 (4)
C2—C16	1.481 (3)	C19—H19	0.9500
C3—C4	1.386 (3)	C20—C21	1.383 (4)
C3—C8	1.390 (3)	C20—H20	0.9500
C4—C5	1.386 (3)	C21—H21	0.9500
C4—H4	0.9500	C22—C23	1.386 (3)
C5—C6	1.389 (3)	C22—C27	1.387 (3)
C5—H5	0.9500	C23—C24	1.388 (3)
C6—C7	1.392 (4)	C23—H23	0.9500
C6—C9	1.512 (3)	C24—C25	1.392 (3)
C7—C8	1.390 (3)	C24—H24	0.9500
C7—H7	0.9500	C25—C26	1.386 (4)
C8—H8	0.9500	C25—C28	1.511 (3)
C9—H9A	0.9800	C26—C27	1.387 (3)
C9—H9B	0.9800	C26—H26	0.9500
C9—H9C	0.9800	C27—H27	0.9500
C10—C11	1.389 (3)	C28—H28A	0.9800
C10—C15	1.396 (3)	C28—H28B	0.9800
C11—C12	1.387 (3)	C28—H28C	0.9800
C11—H11	0.9500	O1—C29	1.400 (4)
C12—C13	1.382 (4)	O1—H10H	0.831 (17)
C12—H12	0.9500	C29—H29A	0.9800
C13—C14	1.380 (4)	C29—H29B	0.9800
C13—H13	0.9500	C29—H29C	0.9800

N2—Pd1—N1	79.13 (8)	C13—C14—H14	119.9
N2—Pd1—Cl2	173.82 (6)	C15—C14—H14	119.9
N1—Pd1—Cl2	95.67 (6)	C14—C15—C10	119.9 (2)
N2—Pd1—Cl1	96.49 (6)	C14—C15—H15	120.0
N1—Pd1—Cl1	172.74 (6)	C10—C15—H15	120.0
Cl2—Pd1—Cl1	89.02 (2)	C17—C16—C21	119.8 (2)
C1—N1—C3	120.6 (2)	C17—C16—C2	119.3 (2)
C1—N1—Pd1	115.20 (17)	C21—C16—C2	120.8 (2)
C3—N1—Pd1	124.03 (15)	C18—C17—C16	119.9 (2)
C2—N2—C22	119.9 (2)	C18—C17—H17	120.1
C2—N2—Pd1	115.61 (16)	C16—C17—H17	120.1
C22—N2—Pd1	123.53 (15)	C19—C18—C17	120.2 (3)
N1—C1—C10	125.8 (2)	C19—C18—H18	119.9
N1—C1—C2	114.2 (2)	C17—C18—H18	119.9
C10—C1—C2	120.0 (2)	C20—C19—C18	119.9 (2)
N2—C2—C16	123.2 (2)	C20—C19—H19	120.1
N2—C2—C1	114.7 (2)	C18—C19—H19	120.1
C16—C2—C1	121.9 (2)	C19—C20—C21	120.5 (3)
C4—C3—C8	120.8 (2)	C19—C20—H20	119.8
C4—C3—N1	117.3 (2)	C21—C20—H20	119.8
C8—C3—N1	121.9 (2)	C20—C21—C16	119.7 (3)
C3—C4—C5	119.2 (2)	C20—C21—H21	120.1
C3—C4—H4	120.4	C16—C21—H21	120.1
C5—C4—H4	120.4	C23—C22—C27	121.0 (2)
C4—C5—C6	121.3 (2)	C23—C22—N2	120.8 (2)
C4—C5—H5	119.4	C27—C22—N2	118.1 (2)
C6—C5—H5	119.4	C22—C23—C24	119.1 (2)
C5—C6—C7	118.3 (2)	C22—C23—H23	120.5
C5—C6—C9	120.8 (2)	C24—C23—H23	120.5
C7—C6—C9	120.8 (2)	C23—C24—C25	121.1 (2)
C8—C7—C6	121.4 (2)	C23—C24—H24	119.5
C8—C7—H7	119.3	C25—C24—H24	119.5
C6—C7—H7	119.3	C26—C25—C24	118.5 (2)
C3—C8—C7	118.8 (2)	C26—C25—C28	120.3 (2)
C3—C8—H8	120.6	C24—C25—C28	121.2 (2)
C7—C8—H8	120.6	C25—C26—C27	121.5 (2)
C6—C9—H9A	109.5	C25—C26—H26	119.2
C6—C9—H9B	109.5	C27—C26—H26	119.2
H9A—C9—H9B	109.5	C26—C27—C22	118.8 (2)
C6—C9—H9C	109.5	C26—C27—H27	120.6
H9A—C9—H9C	109.5	C22—C27—H27	120.6
H9B—C9—H9C	109.5	C25—C28—H28A	109.5
C11—C10—C15	119.5 (2)	C25—C28—H28B	109.5
C11—C10—C1	121.9 (2)	H28A—C28—H28B	109.5
C15—C10—C1	118.6 (2)	C25—C28—H28C	109.5
C12—C11—C10	119.9 (2)	H28A—C28—H28C	109.5
C12—C11—H11	120.0	H28B—C28—H28C	109.5
C10—C11—H11	120.0	C29—O1—H10H	105 (2)
C13—C12—C11	120.4 (3)	O1—C29—H29A	109.5
C13—C12—H12	119.8	O1—C29—H29B	109.5
C11—C12—H12	119.8	H29A—C29—H29B	109.5
C14—C13—C12	120.0 (2)	O1—C29—H29C	109.5
C14—C13—H13	120.0	H29A—C29—H29C	109.5
C12—C13—H13	120.0	H29B—C29—H29C	109.5
C13—C14—C15	120.2 (3)

N2—Pd1—N1—C1	10.15 (16)	N1—C1—C10—C15	−126.3 (3)
Cl2—Pd1—N1—C1	−173.22 (16)	C2—C1—C10—C15	56.1 (3)
N2—Pd1—N1—C3	−174.59 (18)	C15—C10—C11—C12	−0.2 (3)
Cl2—Pd1—N1—C3	2.04 (17)	C1—C10—C11—C12	179.5 (2)
N1—Pd1—N2—C2	−7.07 (17)	C10—C11—C12—C13	1.0 (4)
Cl1—Pd1—N2—C2	167.06 (16)	C11—C12—C13—C14	−0.7 (4)
N1—Pd1—N2—C22	161.36 (19)	C12—C13—C14—C15	−0.4 (4)
Cl1—Pd1—N2—C22	−24.50 (18)	C13—C14—C15—C10	1.2 (4)
C3—N1—C1—C10	−4.4 (3)	C11—C10—C15—C14	−0.9 (3)
Pd1—N1—C1—C10	171.05 (18)	C1—C10—C15—C14	179.4 (2)
C3—N1—C1—C2	173.36 (19)	N2—C2—C16—C17	56.3 (3)
Pd1—N1—C1—C2	−11.2 (2)	C1—C2—C16—C17	−128.8 (2)
C22—N2—C2—C16	9.6 (3)	N2—C2—C16—C21	−122.0 (3)
Pd1—N2—C2—C16	178.51 (18)	C1—C2—C16—C21	52.8 (3)
C22—N2—C2—C1	−165.5 (2)	C21—C16—C17—C18	1.0 (3)
Pd1—N2—C2—C1	3.3 (3)	C2—C16—C17—C18	−177.4 (2)
N1—C1—C2—N2	5.3 (3)	C16—C17—C18—C19	0.2 (4)
C10—C1—C2—N2	−176.8 (2)	C17—C18—C19—C20	−1.2 (4)
N1—C1—C2—C16	−170.0 (2)	C18—C19—C20—C21	1.0 (4)
C10—C1—C2—C16	7.9 (3)	C19—C20—C21—C16	0.2 (4)
C1—N1—C3—C4	−119.0 (2)	C17—C16—C21—C20	−1.2 (4)
Pd1—N1—C3—C4	66.0 (3)	C2—C16—C21—C20	177.2 (2)
C1—N1—C3—C8	61.1 (3)	C2—N2—C22—C23	−115.9 (3)
Pd1—N1—C3—C8	−113.9 (2)	Pd1—N2—C22—C23	76.1 (3)
C8—C3—C4—C5	−4.1 (4)	C2—N2—C22—C27	65.1 (3)
N1—C3—C4—C5	176.0 (2)	Pd1—N2—C22—C27	−102.8 (2)
C3—C4—C5—C6	1.1 (4)	C27—C22—C23—C24	−1.9 (4)
C4—C5—C6—C7	2.6 (4)	N2—C22—C23—C24	179.2 (2)
C4—C5—C6—C9	−174.5 (2)	C22—C23—C24—C25	0.2 (4)
C5—C6—C7—C8	−3.5 (4)	C23—C24—C25—C26	0.9 (4)
C9—C6—C7—C8	173.6 (2)	C23—C24—C25—C28	−178.6 (2)
C4—C3—C8—C7	3.3 (4)	C24—C25—C26—C27	−0.3 (4)
N1—C3—C8—C7	−176.8 (2)	C28—C25—C26—C27	179.2 (2)
C6—C7—C8—C3	0.6 (4)	C25—C26—C27—C22	−1.3 (4)
N1—C1—C10—C11	54.0 (3)	C23—C22—C27—C26	2.4 (4)
C2—C1—C10—C11	−123.6 (3)	N2—C22—C27—C26	−178.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10H···Cl2	0.83 (2)	2.36 (2)	3.161 (2)	163 (3)
C17—H17···Cl2ⁱ	0.95	2.80	3.708 (3)	161
C21—H21···O1ⁱⁱ	0.95	2.48	3.275 (3)	141

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10H···Cl2	0.831 (17)	2.357 (19)	3.161 (2)	163 (3)
C17—H17···Cl2ⁱ	0.95	2.80	3.708 (3)	161.3
C21—H21···O1ⁱⁱ	0.95	2.48	3.275 (3)	141.1

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Acknowledgements

Whittier College is acknowledged for the funds that supported this research. Tammy Le is acknowledged for obtaining the UV–Vis spectrum of the title compound. The upgrade of the diffractometer was made possible by grant No. LEQSF(2011–2012)-ENH-TR-01, administered by the Louisiana Board of Regents.

References

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Volume 71| Part 9| September 2015| Pages m164-m165

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