N-Benzoyl-N',N'-dibutyl­seleno­urea and its palladium(II) complex

The crystal and mol­ecular structures of N-benzoyl-N',N'-dibutyl­seleno­urea (HL), C₁₆H₂₄N₂OSe, and the corresponding complex bis­(N-benzoyl-N',N'-dibutyl­seleno­ureato-[kappa]²Se,O)palladium(II), [Pd(C₁₆H₂₃N₂OSe)₂], are reported. The seleno­urea mol­ecule is characterized by inter­molecular hydrogen bonds between the seleno­amidic H atom and the Se atom of a neighbouring mol­ecule forming a dimer, presumably as a consequence of resonance-assisted hydrogen bonding or [pi]-bonding co-operativity. A second dimeric hydrogen bond is also described. In the palladium complex, the typical square-planar coordination characteristic of such ligands results in a cis-[Pd(L-Se,O)₂] complex.

S1. Comment

The use of metal complexes in which the ligands contain either S or Se as single-source precursors for the synthesis of semiconducting quantum dots has recently attracted interest (Nair et al., 2005; Malik et al., 2005). In this context, we have recently reported the use of [N,N-diethyl-N'-benzoylthio(seleno)urea]cadmium(II) complexes as single-source precursors for the successful synthesis of CdS and CdSe nanoparticles (Bruce et al., 2007). As part of our interest in extending this study to include other metal ions, we have prepared several N,N-dialkyl-N'-benzoylselenoureas and corresponding metal complexes with a view to using these as single-source precursors for nanoparticle synthesis. The related N,N-dialkyl-N'-benzoylthiourea ligands have been studied extensively and are well known to coordinate to a wide variety of first-row transition metal ions (Schuster & Koenig, 1987; Dietze et al., 1991; Beyer et al., 1981). The corresponding N,N-dialkyl-N'-benzoylselenoureas are relatively rare, although some metal complexes of Ni^II and Pd^II derived from N,N-dialkyl-N'-benzoylselenourea have been structurally characterized (Kampf et al., 2004; Bensch & Schuster, 1994). Generally, both N,N-dialkyl-N'-benzoylthioureas and N,N-dialkyl-N'-benzoylselenoureas readily coordinate to metal ions with loss of a thioamidic or selenoamidic H atom, resulting in bidentate coordination through the S(Se) and O donor atoms. Surprisingly, relatively few crystal structures of the unbound ligand N,N-dialkyl-N'-benzoylthiourea and analogous N,N-dialkyl-N'-benzoylselenoureas are available in the literature. We report here the crystal and molecular structures of N,N-dibutyl-N'-benzoylselenourea, HL, (I) (Figs. 1 and 2), and its Pd^II complex, cis-[Pd(L-Se,O)₂], (II) (Fig. 3).

As shown in Fig. 1, compound (I) crystallizes in the space group P2₁/c. The O and Se donor atoms adopt an anti orientation relative to each other as a result of twisting about the N1—C8 bond, to give torsion angles O1—C7—N1—C8 = 0.5 (4)° and C7—N1—C8—Se1 = 121.1 (2)°. The C—N bonds are all shorter than the average C—N bond length of 1.472 (5) Å (Reference for standard value?) (Table 1); the alkyl-substituted selenourea C—N bond [C8—N2 = 1.316 (3) Å] is significantly shorter than the amide [C7—N1 = 1.397 (3) Å] and acyl-substituted selenourea C—N bond [C8—N1 = 1.399 (3) Å]. This reflects the trend observed in the sulfur analogues, where N,N-dibutyl-N'-naphthoylthiourea (Koch et al., 1995) and, more recently, N-acetyl-N',N'-(butane-1,4-diyl)thiourea (Dillen et al., 2006a) and N,N-di-n-butyl-N'-pivaloylthiourea (Dillen et al., 2006b), show that the R,RN—C(S) bond length is, on average, the shortest, followed by the amidic R'C(O)—N bond, while the HN—C(S) thiourea bond is the longest. Moreover, these molecules usually adopt a conformation in the solid state such that the donor atoms S and O assume opposing orientations, the molecule being usually significantly twisted around the longest HN—C(S) thiourea bond.

As shown in Fig. 2, the molecules of (I) are linked through a hydrogen bond between the selenoamidic H atom of one molecule and the Se atom of its neighbour at (-x, 1 - y, 1 - z), with N—H····Se = 2.756 Å, N···Se = 3.538 (2) Å and Se···H—N = 159°, so giving rise to a dimer linked through such hydrogen bonds in the crystal structure. The formation of this dimer represents an example of resonance-assisted hydrogen bonding (RAHB) or π-bond cooperativity (Steiner, 2002) since, in terms of hydrogen bonding, the selenourea moiety consists of donor–acceptor pairs which are connected by a resonant π system, manifested by the shortening of the amide and acyl-substituted C—N bonds. Such an arrangement is also observed in the closely related diethyl analogue, N,N-diethyl-N'-benzoylselenourea (Bruce et al., 2007). This dimer forms an eight-membered ring structure where the atoms H1/N1/C8/Se1/H1ⁱ/N1ⁱ/C8ⁱ/Se1ⁱ [symmetry code: (i) -x, 1 - y, 1 - z] lie in a plane with a maximum deviation of 0.119 (2) Å for atom H1. A second dimeric hydrogen bond is present in (I) between the carbonyl O atom and an H atom on the benzene residue at (-x, 1 - y, -z), with C6—H6.·O1 = 2.481 Å, C6.·O1 = 3.407 (3) Å and O1···H6—C6 = 173.7°. Similarly to the first dimer, this forms a ten-membered ring structure where the atoms O1/C7/C1/C6/H6/O1ⁱⁱ/C7ⁱⁱ/C1ⁱⁱ/C6ⁱⁱ/H6ⁱⁱ [symmetry code: (ii) -x, 1 - y, -z] again lie in a plane, with a maximum deviation of 0.241 (2) Å for atom O1, the angle between these two planes being 82.36 (2)°. It is interesting to note that the second hydrogen bond is not evident in the solid-state structures of other N,N-dialkyl-N'-benzoylselenoureas that have previously been analysed (N,N-dihexyl-N'-benzoylselenourea, N,N-dioctyl-N'-benzoylselenourea and N-benzyl-N-methyl-N'-benzoylselenourea; Bruce & Koch, 2007). These two dimers give rise to the hydrogen-bonded chains shown in Fig. 2 that form in the direction of the c axis. There is little interaction apparent between these chains.

The molecular structure of cis-[Pd(L-Se,O)₂], (II), which crystallizes in the space group P1, is shown in Fig. 3. The generally expected mode of coordination of HL with loss of an H atom, yielding a cis-square-planar complex, is observed. The four donor atoms and Pd metal centre lie in a single coordination plane involving atoms Se1A/O1A/Pd1/Se1B/O1B, with a deviation from planarity of only 0.024 Å [Is this the mean or the maximum deviation? If the latter, please state the atom involved]; the two chelate rings are twisted at an angle of 4.6 (1)° relative to each other, and deviate slightly from perfect planarity by 0.096 and 0.085 Å for atoms Se1A/C8A/N1A/C7A/O1A and Se1B/C8B/N1B/C7B/O1B, respectively. The reduced planarity in the chelate rings is reflected in a puckering of the C7A/N1A/C8A and the C7B/N1B/C8B planes, with atoms N1A and N1B, respectively, lying 0.486 (2) Å below and 0.336 (2) Å above the Se1A/O1A/Pd1/Se1B/O1B plane.

The average Pd—Se and Pd—O bond lengths of 2.345 (3) and 2.041 (1) Å, respectively (Table 3), in (II) compare well with those reported previously for bis[N,N-diisobutyl-N'-(2-fluoro)benzoylselenoureato]palladium(II) (Kampf et al., 2004) and its difluoro analogue, bis[N,N-diisobutyl-N'-(2,6-difluoro)benzoylselenoureato]palladium(II) (Kampf et al., 2005). The C═O and C═Se bonds in (II) are somewhat longer than the corresponding bonds in the ligand HL, as a result of a slight loss of double-bond character in these bonds, presumably due to electron delocalization in the six-membered chelate ring of the metal complex. The relative reduction in the C═Se bond order of (I) on coordination to Pd^II in the complex is also reflected by a significant reduction of the ¹J(⁷⁷Se-¹³C) coupling constant, from 222 Hz in the ligand to 177 Hz in (II), in the ¹³C NMR spectra of these substances in CDCl₃. The electron delocalization in the chelate ring of (II) is, in turn, shown by the slight shortening of the C—N bond lengths compared with the corresponding bonds in the unbound ligand.

Related literature

For related literature, see: Bensch & Schuster (1994); Beyer et al. (1981); Bruce & Koch (2007); Bruce, Koch & Revaprasadu (2007); Dietze et al. (1991); Dillen et al. (2006a, 2006b); Kampf et al. (2004, 2005); Koch et al. (1995); Malik et al. (2005); Nair et al. (2005); Schuster & Koenig (1987); Steiner (2002).

S2. Experimental

The ligand synthesis was carried out under an inert N₂ atmosphere. All reagents and solvents used were commercially available and used without further purification, except for the acetone in the ligand synthesis which was distilled prior to use.

For the synthesis of (I), benzoyl chloride (34.7 mmol) in acetone (20 ml) was added dropwise to an acetone solution (70 ml) of KSeCN (34.7 mmol). The mixture was stirred for 20 min and the development of an orange colour was noted, as well as the formation of a white precipitate. An acetone solution (15 ml) of dibutylamine (34.7 mmol) was added dropwise to this mixture, which was then stirred for 30 min. The mixture was added to cold water (300 ml) and the resulting oil was recrystallized from ethanol to yield crystals suitable for analysis.

For the synthesis of (II), a dichloromethane solution (25 ml) of (I) (1.278 mmol) was added to an aqueous solution (25 ml) of K₂PdCl₄ (0.639 mmol). The solutions were shaken together in a separating funnel and the progression of an orange colour from the aqueous to the organic layer as complexation occurred was noted. An aqueous solution (10 ml) of sodium acetate (2.558 mmol) was added, followed by gentle shaking. Extraction and drying of the organic layer was followed by the addition of ethanol. Slow evaporation from this mixture yielded crystals suitable for analysis. ¹H NMR chemical shifts are quoted relative to the residual CHCl₃ solvent resonance at 7.26 p.p.m., and ¹³C NMR chemical shifts are quoted relative to the CDCl₃ triplet at 77.0 p.p.m. (centre peak). Elemental analyses were performed on a Heraeus Universal Combustion Analyser, Model CHN-Micro.

For N,N-dibutyl-N'-benzoylselenourea, yield 57.5%, m.p. 392.5–394 K. Analysis, found: C 56.6, H 7.1, N 8.2%; C₁₆H₂₄N₂OSe requires: C 56.6, H 7.1, N 8.3%. Spectroscopic analysis: ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 0.90 (t, 3H, ³J_HH = 7.4 Hz, H12/H16), 0.99 (t, 3H, ³J_HH = 7.4 Hz, H12/H16), 1.28 (m, 2H, ³J_HH = 7.5 Hz, H11/H15), 1.45 (m, 2H, ³J_HH = 7.5 Hz, H11/H15), 1.67 (q, 2H, ³J_HH = 7.4 Hz, H10/H14), 1.83 (q, 2H, ³J_HH = 7.4 Hz, H10/H14), 3.55 (t, 2H, ³J_HH = 7.4 Hz, H9/H13), 4.08 (t, 2H, ³J_HH = 7.6 Hz, H9/H13), 7.46 (t, 2H, H3, H5), 7.57 (t, 1H, H4), 7.83 (d, 2H, H2, H6), 8.54 (br s, 1H, N—H); ¹³C NMR (100 MHz, CDCl₃, δ, p.p.m.): 13.6 (C12/C16), 13.8 (C12/C16), 19.9 (C15/C11), 20.0 (C15/C11), 28.7 (C14/C10), 29.7 (C14/C10), 53.7 (C13/C9), 56.4 (C13/C9), 127.8 (C3, C5), 128.8 (C2, C6), 132.5 (C4), 133.0 (C1), 162.1 (C7), 180.9 (C8); ¹J(⁷⁷Se-¹³C) = 222.1 Hz.

For cis-bis(N,N-dibutyl-N'-benzoylselenoureato)palladium(II), yield 94.2%, m.p. 423.5–424.4 K. Analysis, found: C 49.1, H 5.8, N 7.1%; C₃₂H₄₆N₄O₂Se₂Pd requires: C 49.1, H 5.9, N 7.2%. Spectroscopic analysis: ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 0.93 (t, 6H, ³J_HH = 7.4 Hz, H12A/B or H16A/B), 0.98 (t, 6H, ³J_HH = 7.4 Hz, H12A/B or H16A/B), 1.38 (m, 8H, ³J_HH = 7.6 Hz, H11A/B, H15A/B), 1.67 (q, 4H, ³J_HH = 7.7 Hz, H10A/B or H14A/B), 1.76 (q, 4H, ³J_HH = 7.8 Hz, H10A/B or H14A/B), 3.78 (m, 8H, ³J_HH = 7.8 Hz, H9A/B, H13A/B), 7.40 (t, 4H, H3A/B, H5A/B), 7.49 (t, 2H, H4A/B), 8.23 (d, 4H, H2A/B, H6A/B); ¹³C NMR (101 MHz, CDCl₃, δ, p.p.m.): 13.8, 13.9 (C12A/B, C16A/B), 20.2, 20.3 (C11A/B, C15A/B), 29.9, 30.0 (C10A/B, C14A/B), 51.8, 54.7 (C9A/B, C13A/B), 127.9 (C3A/B, C5A/B), 129.7 (C2A/B, C6A/B), 131.4 (C4A/B), 137.2 (C1A/B), 166.7 (C8A/B), 170.8 (C7A/B). ¹J(⁷⁷Se-¹³C) = 176.5 Hz.

S3. Refinement

H atoms involved in hydrogen bonding were located in difference electron-density maps and restrained to N—H = 0.85 Å with U_iso(H) = 1.2U_eq(N). All other H atoms were placed in geometrically calculated positions, with C—H = 0.99 (for –CH₂), 0.98 (for –CH₃) or 0.95 Å (for phenyl H), and refined using a riding model, with U_iso(H) = 1.2U_eq(C) for –CH₂ and phenyl, or 1.5 U_eq(C) for –CH₃.

Computing details

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).

Figures

	Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Neighbouring molecules of (I), showing the weak N—H···Se and C—H···O intermolecular hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) -x, 1 - y, 1 - z; (ii) -x, 1 - y, -z.]
	Fig. 3. The molecular structure of (II), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(I) N-Benzoyl-N',N'-dibutylselenourea

Crystal data

C16H24N2OSe	F(000) = 704
Mr = 339.33	Dx = 1.375 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2631 reflections
a = 10.3880 (17) Å	θ = 2.4–27.2°
b = 15.715 (3) Å	µ = 2.29 mm^−1
c = 10.1518 (16) Å	T = 273 K
β = 98.423 (3)°	Block, yellow
V = 1639.4 (5) Å^3	0.20 × 0.16 × 0.14 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	3775 independent reflections
Radiation source: fine-focus sealed tube	3031 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→13
Tmin = 0.651, Tmax = 0.732	k = −20→20
10228 measured reflections	l = −9→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0423P)^2] where P = (Fo^2 + 2Fc^2)/3
3775 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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
Se1	−0.19333 (2)	0.431363 (15)	0.46477 (2)	0.01660 (9)
O1	−0.00770 (17)	0.41704 (11)	0.12025 (17)	0.0192 (4)
C7	0.0657 (2)	0.42323 (14)	0.2242 (2)	0.0147 (5)
N1	0.0293 (2)	0.40125 (13)	0.3469 (2)	0.0157 (4)
N2	−0.13174 (19)	0.29950 (13)	0.29734 (19)	0.0160 (4)
C2	0.3013 (2)	0.42633 (16)	0.3311 (2)	0.0187 (5)
H2	0.2814	0.3911	0.3989	0.022*
C8	−0.0953 (2)	0.37107 (15)	0.3587 (2)	0.0150 (5)
C11	0.1152 (3)	0.12124 (16)	0.2761 (3)	0.0231 (6)
H11A	0.1624	0.0864	0.3459	0.028*
H11B	0.0573	0.0841	0.2185	0.028*
C12	0.2117 (3)	0.16076 (17)	0.1957 (3)	0.0244 (6)
H12B	0.2630	0.2025	0.2489	0.037*
H12A	0.1654	0.1876	0.1178	0.037*
H12C	0.2676	0.1173	0.1693	0.037*
C14	−0.3490 (2)	0.29865 (16)	0.1623 (2)	0.0192 (5)
H14B	−0.3059	0.2848	0.0865	0.023*
H14A	−0.3571	0.3601	0.1660	0.023*
C15	−0.4839 (2)	0.25914 (18)	0.1427 (3)	0.0253 (6)
H15B	−0.4759	0.1980	0.1332	0.030*
H15A	−0.5246	0.2698	0.2212	0.030*
C5	0.3607 (3)	0.53127 (17)	0.1294 (3)	0.0256 (6)
H5	0.3813	0.5670	0.0625	0.031*
C13	−0.2659 (2)	0.26777 (16)	0.2885 (2)	0.0198 (5)
H13A	−0.3033	0.2872	0.3653	0.024*
H13B	−0.2651	0.2061	0.2896	0.024*
C1	0.2029 (2)	0.45289 (15)	0.2307 (2)	0.0157 (5)
C4	0.4579 (3)	0.50483 (17)	0.2288 (3)	0.0271 (6)
H4	0.5433	0.5223	0.2279	0.032*
C9	−0.0438 (2)	0.24274 (15)	0.2357 (2)	0.0182 (5)
H9A	0.0153	0.2768	0.1920	0.022*
H9B	−0.0947	0.2077	0.1686	0.022*
C3	0.4282 (3)	0.45243 (17)	0.3297 (3)	0.0235 (6)
H3	0.4936	0.4348	0.3966	0.028*
C6	0.2331 (3)	0.50514 (15)	0.1282 (2)	0.0196 (5)
H6	0.1685	0.5222	0.0600	0.024*
C10	0.0342 (3)	0.18581 (16)	0.3390 (2)	0.0213 (6)
H10A	0.0912	0.2207	0.4011	0.026*
H10B	−0.0249	0.1561	0.3887	0.026*
C16	−0.5707 (3)	0.29393 (19)	0.0215 (3)	0.0268 (6)
H16C	−0.5294	0.2856	−0.0562	0.040*
H16A	−0.5849	0.3536	0.0335	0.040*
H16B	−0.6526	0.2646	0.0104	0.040*
H1	0.062 (3)	0.4321 (16)	0.409 (3)	0.015 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.01405 (14)	0.01869 (14)	0.01733 (14)	−0.00070 (10)	0.00318 (9)	−0.00252 (10)
O1	0.0197 (9)	0.0215 (9)	0.0154 (9)	−0.0010 (7)	−0.0007 (7)	0.0010 (7)
C7	0.0161 (12)	0.0119 (11)	0.0160 (12)	0.0031 (9)	0.0022 (10)	−0.0006 (9)
N1	0.0156 (11)	0.0186 (10)	0.0125 (11)	−0.0028 (9)	0.0010 (8)	−0.0030 (9)
N2	0.0161 (10)	0.0172 (10)	0.0140 (10)	−0.0014 (8)	−0.0001 (8)	−0.0008 (8)
C2	0.0193 (13)	0.0222 (13)	0.0149 (12)	0.0014 (11)	0.0032 (10)	−0.0023 (10)
C8	0.0144 (12)	0.0182 (12)	0.0117 (12)	−0.0011 (10)	0.0000 (9)	0.0024 (9)
C11	0.0246 (14)	0.0181 (13)	0.0254 (15)	0.0033 (11)	−0.0002 (11)	0.0051 (11)
C12	0.0216 (14)	0.0260 (14)	0.0255 (14)	0.0029 (12)	0.0029 (11)	−0.0011 (11)
C14	0.0179 (13)	0.0234 (13)	0.0162 (13)	−0.0009 (11)	0.0020 (10)	−0.0013 (10)
C15	0.0227 (14)	0.0294 (15)	0.0221 (14)	−0.0069 (12)	−0.0020 (11)	0.0022 (11)
C5	0.0288 (15)	0.0225 (14)	0.0279 (16)	−0.0047 (12)	0.0117 (12)	0.0018 (11)
C13	0.0204 (13)	0.0189 (13)	0.0196 (13)	−0.0046 (10)	0.0014 (10)	−0.0010 (10)
C1	0.0160 (12)	0.0140 (11)	0.0173 (13)	0.0023 (10)	0.0034 (10)	−0.0039 (9)
C4	0.0180 (14)	0.0286 (15)	0.0363 (17)	−0.0047 (12)	0.0095 (12)	−0.0079 (12)
C9	0.0206 (13)	0.0165 (12)	0.0166 (13)	0.0007 (10)	−0.0002 (10)	−0.0038 (10)
C3	0.0166 (13)	0.0292 (14)	0.0240 (14)	0.0025 (11)	0.0008 (11)	−0.0071 (11)
C6	0.0238 (14)	0.0187 (12)	0.0168 (13)	0.0030 (11)	0.0046 (10)	0.0002 (10)
C10	0.0237 (14)	0.0226 (13)	0.0176 (13)	−0.0012 (11)	0.0036 (11)	0.0023 (10)
C16	0.0209 (14)	0.0376 (16)	0.0210 (14)	−0.0050 (12)	0.0003 (11)	0.0030 (12)

Geometric parameters (Å, º)

Se1—C8	1.848 (2)	C14—H14A	0.9700
O1—C7	1.212 (3)	C15—C16	1.517 (4)
C7—N1	1.397 (3)	C15—H15B	0.9700
C7—C1	1.492 (3)	C15—H15A	0.9700
N1—C8	1.399 (3)	C5—C4	1.383 (4)
N1—H1	0.83 (3)	C5—C6	1.386 (4)
N2—C8	1.314 (3)	C5—H5	0.9300
N2—C13	1.470 (3)	C13—H13A	0.9700
N2—C9	1.480 (3)	C13—H13B	0.9700
C2—C3	1.383 (4)	C1—C6	1.397 (3)
C2—C1	1.397 (3)	C4—C3	1.384 (4)
C2—H2	0.9300	C4—H4	0.9300
C11—C12	1.515 (3)	C9—C10	1.519 (3)
C11—C10	1.517 (3)	C9—H9A	0.9700
C11—H11A	0.9700	C9—H9B	0.9700
C11—H11B	0.9700	C3—H3	0.9300
C12—H12B	0.9600	C6—H6	0.9300
C12—H12A	0.9600	C10—H10A	0.9700
C12—H12C	0.9600	C10—H10B	0.9700
C14—C13	1.516 (3)	C16—H16C	0.9600
C14—C15	1.520 (3)	C16—H16A	0.9600
C14—H14B	0.9700	C16—H16B	0.9600
O1—C7—N1	122.6 (2)	C4—C5—C6	120.8 (3)
O1—C7—C1	122.6 (2)	C4—C5—H5	119.6
N1—C7—C1	114.8 (2)	C6—C5—H5	119.6
C7—N1—C8	122.3 (2)	N2—C13—C14	111.09 (19)
C7—N1—H1	113.3 (18)	N2—C13—H13A	109.4
C8—N1—H1	114.8 (18)	C14—C13—H13A	109.4
C8—N2—C13	121.6 (2)	N2—C13—H13B	109.4
C8—N2—C9	124.3 (2)	C14—C13—H13B	109.4
C13—N2—C9	114.10 (19)	H13A—C13—H13B	108.0
C3—C2—C1	120.0 (2)	C6—C1—C2	119.9 (2)
C3—C2—H2	120.0	C6—C1—C7	117.9 (2)
C1—C2—H2	120.0	C2—C1—C7	122.0 (2)
N2—C8—N1	117.1 (2)	C5—C4—C3	120.1 (3)
N2—C8—Se1	124.72 (18)	C5—C4—H4	120.0
N1—C8—Se1	118.14 (17)	C3—C4—H4	120.0
C12—C11—C10	113.8 (2)	N2—C9—C10	111.30 (19)
C12—C11—H11A	108.8	N2—C9—H9A	109.4
C10—C11—H11A	108.8	C10—C9—H9A	109.4
C12—C11—H11B	108.8	N2—C9—H9B	109.4
C10—C11—H11B	108.8	C10—C9—H9B	109.4
H11A—C11—H11B	107.7	H9A—C9—H9B	108.0
C11—C12—H12B	109.5	C2—C3—C4	120.0 (3)
C11—C12—H12A	109.5	C2—C3—H3	120.0
H12B—C12—H12A	109.5	C4—C3—H3	120.0
C11—C12—H12C	109.5	C5—C6—C1	119.1 (2)
H12B—C12—H12C	109.5	C5—C6—H6	120.5
H12A—C12—H12C	109.5	C1—C6—H6	120.5
C13—C14—C15	112.3 (2)	C11—C10—C9	112.1 (2)
C13—C14—H14B	109.1	C11—C10—H10A	109.2
C15—C14—H14B	109.1	C9—C10—H10A	109.2
C13—C14—H14A	109.1	C11—C10—H10B	109.2
C15—C14—H14A	109.1	C9—C10—H10B	109.2
H14B—C14—H14A	107.9	H10A—C10—H10B	107.9
C16—C15—C14	112.7 (2)	C15—C16—H16C	109.5
C16—C15—H15B	109.0	C15—C16—H16A	109.5
C14—C15—H15B	109.0	H16C—C16—H16A	109.5
C16—C15—H15A	109.0	C15—C16—H16B	109.5
C14—C15—H15A	109.0	H16C—C16—H16B	109.5
H15B—C15—H15A	107.8	H16A—C16—H16B	109.5
O1—C7—N1—C8	−0.5 (4)	O1—C7—C1—C6	25.4 (3)
C1—C7—N1—C8	−179.1 (2)	N1—C7—C1—C6	−156.0 (2)
C13—N2—C8—N1	−172.0 (2)	O1—C7—C1—C2	−151.1 (2)
C9—N2—C8—N1	10.1 (3)	N1—C7—C1—C2	27.5 (3)
C13—N2—C8—Se1	10.9 (3)	C6—C5—C4—C3	−0.8 (4)
C9—N2—C8—Se1	−166.99 (17)	C8—N2—C9—C10	81.4 (3)
C7—N1—C8—N2	61.6 (3)	C13—N2—C9—C10	−96.7 (2)
C7—N1—C8—Se1	−121.1 (2)	C1—C2—C3—C4	−0.1 (4)
C13—C14—C15—C16	176.3 (2)	C5—C4—C3—C2	0.1 (4)
C8—N2—C13—C14	92.0 (3)	C4—C5—C6—C1	1.4 (4)
C9—N2—C13—C14	−89.9 (2)	C2—C1—C6—C5	−1.3 (4)
C15—C14—C13—N2	173.7 (2)	C7—C1—C6—C5	−177.9 (2)
C3—C2—C1—C6	0.6 (4)	C12—C11—C10—C9	58.9 (3)
C3—C2—C1—C7	177.1 (2)	N2—C9—C10—C11	174.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Se1^i	0.83 (3)	2.76 (3)	3.539 (2)	159 (2)
C6—H6···O1^ii	0.93	2.48	3.407 (3)	174

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

(II) bis(N-benzoyl-N',N'-dibutylselenoureato-κ²Se,O)palladium(II)

Crystal data

[Pd(C16H23N2OSe)2]	Z = 2
Mr = 783.05	F(000) = 792
Triclinic, P1	Dx = 1.593 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9302 (8) Å	Cell parameters from 6089 reflections
b = 10.9315 (9) Å	θ = 2.5–28.1°
c = 15.4119 (13) Å	µ = 2.83 mm^−1
α = 80.216 (1)°	T = 173 K
β = 88.291 (1)°	Prism, brown
γ = 81.867 (1)°	0.09 × 0.08 × 0.08 mm
V = 1632.0 (2) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	7329 independent reflections
Radiation source: fine-focus sealed tube	6802 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −13→13
Tmin = 0.785, Tmax = 0.797	k = −14→13
18809 measured reflections	l = −19→20

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) = 0.056	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0306P)^2 + 0.7045P] where P = (Fo^2 + 2Fc^2)/3
7329 reflections	(Δ/σ)max = 0.001
374 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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
Pd1	0.770245 (12)	0.454364 (12)	0.247821 (8)	0.01375 (4)
Se1A	0.547248 (17)	0.556941 (16)	0.222043 (11)	0.01692 (5)
Se1B	0.817164 (18)	0.632990 (16)	0.299743 (12)	0.01941 (5)
O1B	0.96158 (13)	0.36044 (12)	0.27371 (9)	0.0201 (3)
O1A	0.73153 (13)	0.29951 (12)	0.20070 (8)	0.0194 (3)
N2A	0.37899 (14)	0.53175 (13)	0.08718 (9)	0.0146 (3)
C9B	1.14223 (18)	0.61760 (17)	0.46837 (11)	0.0163 (3)
H13A	1.1755	0.5268	0.4744	0.020*
H13B	1.1302	0.6388	0.5283	0.020*
N1B	1.07650 (14)	0.48060 (14)	0.35262 (9)	0.0147 (3)
N2B	1.00896 (14)	0.64422 (13)	0.42335 (9)	0.0147 (3)
C9A	0.30972 (17)	0.46624 (17)	0.02896 (11)	0.0157 (3)
H9AA	0.3769	0.4026	0.0070	0.019*
H9AB	0.2725	0.5274	−0.0225	0.019*
C8A	0.48186 (17)	0.46962 (16)	0.13838 (11)	0.0143 (3)
C10A	0.19479 (17)	0.40237 (17)	0.07591 (11)	0.0169 (3)
H10A	0.2310	0.3447	0.1293	0.020*
H11B	0.1249	0.4666	0.0949	0.020*
C10B	1.24854 (17)	0.69094 (17)	0.41918 (11)	0.0176 (4)
H12A	1.2202	0.7817	0.4185	0.021*
H12B	1.2546	0.6763	0.3575	0.021*
C8B	0.98127 (17)	0.57589 (16)	0.36358 (11)	0.0145 (3)
C2B	1.31349 (18)	0.31619 (18)	0.33731 (11)	0.0184 (4)
H2B	1.3220	0.3970	0.3497	0.022*
C14A	0.21303 (18)	0.68508 (17)	0.15592 (11)	0.0180 (4)
H15A	0.1257	0.6705	0.1329	0.022*
H15B	0.2341	0.6239	0.2106	0.022*
C3A	0.5343 (2)	−0.02689 (18)	0.10928 (12)	0.0224 (4)
H3A	0.4569	−0.0574	0.0907	0.027*
C15A	0.1986 (2)	0.81801 (18)	0.17714 (12)	0.0223 (4)
H17A	0.1290	0.8255	0.2240	0.027*
H17B	0.2861	0.8311	0.2008	0.027*
C6B	1.17617 (18)	0.17012 (17)	0.29705 (11)	0.0183 (4)
H6B	1.0908	0.1515	0.2806	0.022*
C4B	1.41481 (19)	0.10644 (19)	0.32571 (12)	0.0230 (4)
H4B	1.4924	0.0440	0.3298	0.028*
C6A	0.76049 (18)	0.06160 (17)	0.16393 (11)	0.0176 (3)
H6A	0.8382	0.0916	0.1825	0.021*
C2A	0.52651 (18)	0.09833 (17)	0.11778 (12)	0.0187 (4)
H2A	0.4444	0.1536	0.1039	0.022*
C5B	1.28965 (19)	0.07855 (18)	0.30357 (12)	0.0217 (4)
H5B	1.2814	−0.0031	0.2928	0.026*
C5A	0.76796 (19)	−0.06295 (17)	0.15395 (12)	0.0208 (4)
H5A	0.8510	−0.1178	0.1651	0.025*
C7A	0.63071 (17)	0.27561 (16)	0.16131 (10)	0.0143 (3)
C16B	0.8200 (2)	1.10473 (18)	0.40251 (13)	0.0255 (4)
H25A	0.9098	1.1236	0.4162	0.038*
H25B	0.7493	1.1591	0.4290	0.038*
H25C	0.8081	1.1194	0.3385	0.038*
C13B	0.91040 (18)	0.74404 (16)	0.45145 (11)	0.0172 (3)
H26A	0.9239	0.7430	0.5150	0.021*
H26B	0.8177	0.7238	0.4445	0.021*
C12A	0.00536 (19)	0.27661 (19)	0.06108 (13)	0.0244 (4)
H27A	0.0324	0.2216	0.1167	0.037*
H27B	−0.0330	0.2287	0.0220	0.037*
H27C	−0.0631	0.3458	0.0728	0.037*
C1B	1.18762 (17)	0.28944 (17)	0.31464 (10)	0.0152 (3)
C1A	0.63908 (17)	0.14309 (16)	0.14675 (10)	0.0146 (3)
C4A	0.6543 (2)	−0.10739 (17)	0.12768 (12)	0.0219 (4)
H4A	0.6588	−0.1932	0.1223	0.026*
C11A	0.12917 (19)	0.32892 (19)	0.01731 (12)	0.0225 (4)
H31A	0.1015	0.3844	−0.0388	0.027*
H31B	0.1966	0.2590	0.0035	0.027*
C11B	1.38801 (18)	0.65209 (19)	0.46216 (13)	0.0231 (4)
H32A	1.3774	0.6459	0.5268	0.028*
H32B	1.4262	0.5681	0.4497	0.028*
C13A	0.32587 (17)	0.66404 (16)	0.08770 (11)	0.0166 (3)
H33A	0.2901	0.7019	0.0285	0.020*
H33B	0.4019	0.7085	0.0994	0.020*
C15B	0.80887 (19)	0.96858 (18)	0.43930 (13)	0.0227 (4)
H34A	0.7178	0.9505	0.4254	0.027*
H34B	0.8169	0.9556	0.5042	0.027*
C16A	0.1590 (2)	0.92151 (19)	0.09893 (13)	0.0271 (4)
H35A	0.2259	0.9138	0.0514	0.041*
H35B	0.1569	1.0034	0.1171	0.041*
H35C	0.0689	0.9138	0.0780	0.041*
C7B	1.06315 (17)	0.38560 (16)	0.31088 (11)	0.0149 (3)
C14B	0.91719 (18)	0.87620 (16)	0.40298 (11)	0.0175 (3)
H38A	0.9021	0.8799	0.3393	0.021*
H38B	1.0085	0.8994	0.4103	0.021*
C3B	1.42681 (19)	0.22501 (19)	0.34190 (12)	0.0226 (4)
H3B	1.5130	0.2442	0.3562	0.027*
C12B	1.4869 (2)	0.7439 (2)	0.42947 (15)	0.0349 (5)
H40A	1.4956	0.7524	0.3653	0.052*
H40B	1.5760	0.7128	0.4564	0.052*
H40C	1.4529	0.8257	0.4456	0.052*
N1A	0.52080 (14)	0.35107 (14)	0.12834 (9)	0.0151 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.01128 (7)	0.01286 (7)	0.01776 (7)	−0.00194 (5)	−0.00408 (5)	−0.00350 (5)
Se1A	0.01248 (9)	0.01599 (9)	0.02368 (9)	−0.00062 (6)	−0.00464 (7)	−0.00762 (7)
Se1B	0.01574 (9)	0.01337 (9)	0.02999 (10)	0.00011 (6)	−0.00997 (7)	−0.00614 (7)
O1B	0.0150 (6)	0.0183 (6)	0.0285 (7)	−0.0003 (5)	−0.0069 (5)	−0.0090 (5)
O1A	0.0146 (6)	0.0170 (6)	0.0282 (7)	−0.0010 (5)	−0.0069 (5)	−0.0081 (5)
N2A	0.0122 (7)	0.0149 (7)	0.0168 (7)	−0.0030 (5)	−0.0010 (5)	−0.0023 (6)
C9B	0.0168 (8)	0.0167 (8)	0.0160 (8)	−0.0036 (6)	−0.0051 (6)	−0.0026 (6)
N1B	0.0125 (7)	0.0168 (7)	0.0155 (6)	−0.0035 (5)	−0.0011 (5)	−0.0032 (6)
N2B	0.0136 (7)	0.0132 (7)	0.0177 (7)	−0.0023 (5)	−0.0016 (5)	−0.0029 (5)
C9A	0.0134 (8)	0.0197 (9)	0.0144 (7)	−0.0025 (6)	−0.0037 (6)	−0.0034 (7)
C8A	0.0111 (8)	0.0174 (8)	0.0150 (7)	−0.0051 (6)	0.0012 (6)	−0.0024 (6)
C10A	0.0132 (8)	0.0204 (9)	0.0183 (8)	−0.0046 (7)	0.0000 (6)	−0.0050 (7)
C10B	0.0125 (8)	0.0206 (9)	0.0193 (8)	−0.0013 (7)	−0.0026 (6)	−0.0024 (7)
C8B	0.0136 (8)	0.0150 (8)	0.0149 (7)	−0.0052 (6)	−0.0024 (6)	0.0009 (6)
C2B	0.0171 (9)	0.0207 (9)	0.0183 (8)	−0.0027 (7)	0.0007 (7)	−0.0056 (7)
C14A	0.0166 (8)	0.0181 (9)	0.0188 (8)	−0.0017 (7)	0.0002 (7)	−0.0028 (7)
C3A	0.0237 (10)	0.0217 (10)	0.0251 (9)	−0.0097 (7)	−0.0017 (7)	−0.0077 (7)
C15A	0.0243 (10)	0.0224 (10)	0.0209 (8)	−0.0006 (8)	−0.0006 (7)	−0.0076 (7)
C6B	0.0182 (9)	0.0194 (9)	0.0177 (8)	−0.0020 (7)	−0.0015 (7)	−0.0049 (7)
C4B	0.0196 (9)	0.0265 (10)	0.0199 (8)	0.0059 (7)	0.0004 (7)	−0.0035 (7)
C6A	0.0169 (8)	0.0180 (9)	0.0183 (8)	−0.0032 (7)	−0.0009 (7)	−0.0032 (7)
C2A	0.0184 (9)	0.0169 (9)	0.0214 (8)	−0.0031 (7)	−0.0019 (7)	−0.0044 (7)
C5B	0.0246 (10)	0.0200 (9)	0.0197 (8)	0.0018 (7)	0.0000 (7)	−0.0054 (7)
C5A	0.0222 (9)	0.0166 (9)	0.0221 (9)	0.0003 (7)	0.0010 (7)	−0.0019 (7)
C7A	0.0146 (8)	0.0160 (8)	0.0131 (7)	−0.0044 (6)	0.0013 (6)	−0.0029 (6)
C16B	0.0289 (10)	0.0205 (10)	0.0264 (9)	0.0049 (8)	−0.0038 (8)	−0.0086 (8)
C13B	0.0172 (8)	0.0168 (9)	0.0187 (8)	−0.0029 (7)	0.0017 (7)	−0.0064 (7)
C12A	0.0198 (9)	0.0264 (10)	0.0283 (10)	−0.0082 (8)	−0.0057 (8)	−0.0038 (8)
C1B	0.0140 (8)	0.0189 (9)	0.0120 (7)	−0.0008 (6)	0.0002 (6)	−0.0017 (6)
C1A	0.0169 (8)	0.0142 (8)	0.0130 (7)	−0.0036 (6)	0.0005 (6)	−0.0019 (6)
C4A	0.0303 (10)	0.0141 (9)	0.0225 (9)	−0.0066 (7)	0.0043 (8)	−0.0041 (7)
C11A	0.0213 (9)	0.0273 (10)	0.0213 (9)	−0.0081 (8)	−0.0022 (7)	−0.0069 (8)
C11B	0.0159 (9)	0.0258 (10)	0.0278 (9)	0.0039 (7)	−0.0066 (7)	−0.0091 (8)
C13A	0.0153 (8)	0.0142 (8)	0.0189 (8)	−0.0007 (6)	−0.0022 (6)	0.0002 (7)
C15B	0.0186 (9)	0.0221 (10)	0.0273 (9)	0.0014 (7)	0.0015 (7)	−0.0074 (8)
C16A	0.0286 (10)	0.0209 (10)	0.0311 (10)	0.0019 (8)	−0.0040 (8)	−0.0058 (8)
C7B	0.0149 (8)	0.0153 (8)	0.0138 (7)	−0.0020 (6)	−0.0002 (6)	−0.0002 (6)
C14B	0.0163 (8)	0.0161 (9)	0.0199 (8)	−0.0003 (7)	−0.0003 (7)	−0.0041 (7)
C3B	0.0143 (9)	0.0319 (11)	0.0210 (9)	0.0002 (7)	−0.0013 (7)	−0.0054 (8)
C12B	0.0165 (10)	0.0572 (15)	0.0344 (11)	−0.0103 (9)	0.0010 (8)	−0.0130 (10)
N1A	0.0130 (7)	0.0155 (7)	0.0169 (7)	−0.0032 (5)	−0.0027 (5)	−0.0019 (6)

Geometric parameters (Å, º)

Pd1—O1A	2.0395 (12)	C4B—C3B	1.383 (3)
Pd1—O1B	2.0439 (12)	C4B—C5B	1.386 (3)
Pd1—Se1B	2.3411 (3)	C4B—H4B	0.9500
Pd1—Se1A	2.3489 (3)	C6A—C5A	1.387 (3)
Se1A—C8A	1.9076 (17)	C6A—C1A	1.397 (2)
Se1B—C8B	1.9006 (16)	C6A—H6A	0.9500
O1B—C7B	1.260 (2)	C2A—C1A	1.395 (2)
O1A—C7A	1.266 (2)	C2A—H2A	0.9500
N2A—C8A	1.341 (2)	C5B—H5B	0.9500
N2A—C13A	1.469 (2)	C5A—C4A	1.387 (3)
N2A—C9A	1.478 (2)	C5A—H5A	0.9500
C9B—N2B	1.481 (2)	C7A—N1A	1.329 (2)
C9B—C10B	1.522 (3)	C7A—C1A	1.494 (2)
C9B—H13A	0.9900	C16B—C15B	1.518 (3)
C9B—H13B	0.9900	C16B—H25A	0.9800
N1B—C8B	1.334 (2)	C16B—H25B	0.9800
N1B—C7B	1.335 (2)	C16B—H25C	0.9800
N2B—C8B	1.338 (2)	C13B—C14B	1.519 (2)
N2B—C13B	1.473 (2)	C13B—H26A	0.9900
C9A—C10A	1.523 (2)	C13B—H26B	0.9900
C9A—H9AA	0.9900	C12A—C11A	1.521 (3)
C9A—H9AB	0.9900	C12A—H27A	0.9800
C8A—N1A	1.333 (2)	C12A—H27B	0.9800
C10A—C11A	1.521 (2)	C12A—H27C	0.9800
C10A—H10A	0.9900	C1B—C7B	1.501 (2)
C10A—H11B	0.9900	C4A—H4A	0.9500
C10B—C11B	1.526 (2)	C11A—H31A	0.9900
C10B—H12A	0.9900	C11A—H31B	0.9900
C10B—H12B	0.9900	C11B—C12B	1.517 (3)
C2B—C3B	1.389 (2)	C11B—H32A	0.9900
C2B—C1B	1.391 (2)	C11B—H32B	0.9900
C2B—H2B	0.9500	C13A—H33A	0.9900
C14A—C15A	1.529 (3)	C13A—H33B	0.9900
C14A—C13A	1.534 (2)	C15B—C14B	1.529 (2)
C14A—H15A	0.9900	C15B—H34A	0.9900
C14A—H15B	0.9900	C15B—H34B	0.9900
C3A—C4A	1.383 (3)	C16A—H35A	0.9800
C3A—C2A	1.388 (3)	C16A—H35B	0.9800
C3A—H3A	0.9500	C16A—H35C	0.9800
C15A—C16A	1.525 (3)	C14B—H38A	0.9900
C15A—H17A	0.9900	C14B—H38B	0.9900
C15A—H17B	0.9900	C3B—H3B	0.9500
C6B—C5B	1.391 (2)	C12B—H40A	0.9800
C6B—C1B	1.397 (3)	C12B—H40B	0.9800
C6B—H6B	0.9500	C12B—H40C	0.9800
O1A—Pd1—O1B	86.08 (5)	C4A—C5A—H5A	120.0
O1A—Pd1—Se1B	178.98 (4)	C6A—C5A—H5A	120.0
O1B—Pd1—Se1B	93.59 (4)	O1A—C7A—N1A	130.00 (16)
O1A—Pd1—Se1A	93.12 (3)	O1A—C7A—C1A	114.96 (14)
O1B—Pd1—Se1A	177.91 (4)	N1A—C7A—C1A	115.00 (15)
Se1B—Pd1—Se1A	87.244 (8)	C15B—C16B—H25A	109.5
C8A—Se1A—Pd1	102.73 (5)	C15B—C16B—H25B	109.5
C8B—Se1B—Pd1	103.40 (5)	H25A—C16B—H25B	109.5
C7B—O1B—Pd1	132.90 (12)	C15B—C16B—H25C	109.5
C7A—O1A—Pd1	132.89 (11)	H25A—C16B—H25C	109.5
C8A—N2A—C13A	123.06 (14)	H25B—C16B—H25C	109.5
C8A—N2A—C9A	120.23 (14)	N2B—C13B—C14B	116.20 (15)
C13A—N2A—C9A	116.67 (13)	N2B—C13B—H26A	108.2
N2B—C9B—C10B	112.65 (14)	C14B—C13B—H26A	108.2
N2B—C9B—H13A	109.1	N2B—C13B—H26B	108.2
C10B—C9B—H13A	109.1	C14B—C13B—H26B	108.2
N2B—C9B—H13B	109.1	H26A—C13B—H26B	107.4
C10B—C9B—H13B	109.1	C11A—C12A—H27A	109.5
H13A—C9B—H13B	107.8	C11A—C12A—H27B	109.5
C8B—N1B—C7B	127.02 (15)	H27A—C12A—H27B	109.5
C8B—N2B—C13B	123.47 (14)	C11A—C12A—H27C	109.5
C8B—N2B—C9B	120.27 (14)	H27A—C12A—H27C	109.5
C13B—N2B—C9B	116.21 (14)	H27B—C12A—H27C	109.5
N2A—C9A—C10A	112.28 (14)	C2B—C1B—C6B	119.47 (16)
N2A—C9A—H9AA	109.1	C2B—C1B—C7B	121.12 (16)
C10A—C9A—H9AA	109.1	C6B—C1B—C7B	119.40 (16)
N2A—C9A—H9AB	109.1	C2A—C1A—C6A	119.23 (16)
C10A—C9A—H9AB	109.1	C2A—C1A—C7A	121.03 (15)
H9AA—C9A—H9AB	107.9	C6A—C1A—C7A	119.73 (15)
N1A—C8A—N2A	115.79 (15)	C3A—C4A—C5A	120.04 (17)
N1A—C8A—Se1A	127.55 (12)	C3A—C4A—H4A	120.0
N2A—C8A—Se1A	116.52 (12)	C5A—C4A—H4A	120.0
C11A—C10A—C9A	112.05 (15)	C12A—C11A—C10A	111.80 (15)
C11A—C10A—H10A	109.2	C12A—C11A—H31A	109.3
C9A—C10A—H10A	109.2	C10A—C11A—H31A	109.3
C11A—C10A—H11B	109.2	C12A—C11A—H31B	109.3
C9A—C10A—H11B	109.2	C10A—C11A—H31B	109.3
H10A—C10A—H11B	107.9	H31A—C11A—H31B	107.9
C9B—C10B—C11B	111.40 (15)	C12B—C11B—C10B	112.47 (16)
C9B—C10B—H12A	109.3	C12B—C11B—H32A	109.1
C11B—C10B—H12A	109.3	C10B—C11B—H32A	109.1
C9B—C10B—H12B	109.3	C12B—C11B—H32B	109.1
C11B—C10B—H12B	109.3	C10B—C11B—H32B	109.1
H12A—C10B—H12B	108.0	H32A—C11B—H32B	107.8
N1B—C8B—N2B	115.72 (14)	N2A—C13A—C14A	114.31 (14)
N1B—C8B—Se1B	128.10 (13)	N2A—C13A—H33A	108.7
N2B—C8B—Se1B	116.04 (12)	C14A—C13A—H33A	108.7
C3B—C2B—C1B	120.11 (17)	N2A—C13A—H33B	108.7
C3B—C2B—H2B	119.9	C14A—C13A—H33B	108.7
C1B—C2B—H2B	119.9	H33A—C13A—H33B	107.6
C15A—C14A—C13A	111.52 (15)	C16B—C15B—C14B	113.35 (16)
C15A—C14A—H15A	109.3	C16B—C15B—H34A	108.9
C13A—C14A—H15A	109.3	C14B—C15B—H34A	108.9
C15A—C14A—H15B	109.3	C16B—C15B—H34B	108.9
C13A—C14A—H15B	109.3	C14B—C15B—H34B	108.9
H15A—C14A—H15B	108.0	H34A—C15B—H34B	107.7
C4A—C3A—C2A	120.31 (17)	C15A—C16A—H35A	109.5
C4A—C3A—H3A	119.8	C15A—C16A—H35B	109.5
C2A—C3A—H3A	119.8	H35A—C16A—H35B	109.5
C16A—C15A—C14A	114.54 (15)	C15A—C16A—H35C	109.5
C16A—C15A—H17A	108.6	H35A—C16A—H35C	109.5
C14A—C15A—H17A	108.6	H35B—C16A—H35C	109.5
C16A—C15A—H17B	108.6	O1B—C7B—N1B	130.59 (16)
C14A—C15A—H17B	108.6	O1B—C7B—C1B	115.43 (15)
H17A—C15A—H17B	107.6	N1B—C7B—C1B	113.84 (15)
C5B—C6B—C1B	120.04 (17)	C13B—C14B—C15B	109.94 (15)
C5B—C6B—H6B	120.0	C13B—C14B—H38A	109.7
C1B—C6B—H6B	120.0	C15B—C14B—H38A	109.7
C3B—C4B—C5B	120.05 (17)	C13B—C14B—H38B	109.7
C3B—C4B—H4B	120.0	C15B—C14B—H38B	109.7
C5B—C4B—H4B	120.0	H38A—C14B—H38B	108.2
C5A—C6A—C1A	120.27 (17)	C4B—C3B—C2B	120.30 (18)
C5A—C6A—H6A	119.9	C4B—C3B—H3B	119.8
C1A—C6A—H6A	119.9	C2B—C3B—H3B	119.8
C3A—C2A—C1A	120.08 (16)	C11B—C12B—H40A	109.5
C3A—C2A—H2A	120.0	C11B—C12B—H40B	109.5
C1A—C2A—H2A	120.0	H40A—C12B—H40B	109.5
C4B—C5B—C6B	120.01 (18)	C11B—C12B—H40C	109.5
C4B—C5B—H5B	120.0	H40A—C12B—H40C	109.5
C6B—C5B—H5B	120.0	H40B—C12B—H40C	109.5
C4A—C5A—C6A	120.03 (17)	C7A—N1A—C8A	127.50 (15)
O1A—Pd1—Se1A—C8A	−19.43 (6)	C9B—N2B—C13B—C14B	88.86 (18)
Se1B—Pd1—Se1A—C8A	159.62 (5)	C3B—C2B—C1B—C6B	0.3 (3)
O1B—Pd1—Se1B—C8B	−15.02 (7)	C3B—C2B—C1B—C7B	178.85 (16)
Se1A—Pd1—Se1B—C8B	163.06 (5)	C5B—C6B—C1B—C2B	1.0 (3)
O1A—Pd1—O1B—C7B	−175.66 (17)	C5B—C6B—C1B—C7B	−177.55 (16)
Se1B—Pd1—O1B—C7B	5.30 (16)	C3A—C2A—C1A—C6A	2.3 (3)
O1B—Pd1—O1A—C7A	−173.48 (16)	C3A—C2A—C1A—C7A	−176.48 (16)
Se1A—Pd1—O1A—C7A	8.45 (16)	C5A—C6A—C1A—C2A	−1.3 (3)
C10B—C9B—N2B—C8B	89.66 (19)	C5A—C6A—C1A—C7A	177.48 (16)
C10B—C9B—N2B—C13B	−93.06 (18)	O1A—C7A—C1A—C2A	169.17 (16)
C8A—N2A—C9A—C10A	86.64 (19)	N1A—C7A—C1A—C2A	−13.0 (2)
C13A—N2A—C9A—C10A	−91.15 (17)	O1A—C7A—C1A—C6A	−9.6 (2)
C13A—N2A—C8A—N1A	−178.13 (15)	N1A—C7A—C1A—C6A	168.28 (16)
C9A—N2A—C8A—N1A	4.2 (2)	C2A—C3A—C4A—C5A	−0.6 (3)
C13A—N2A—C8A—Se1A	5.8 (2)	C6A—C5A—C4A—C3A	1.6 (3)
C9A—N2A—C8A—Se1A	−171.82 (12)	C9A—C10A—C11A—C12A	−174.11 (15)
Pd1—Se1A—C8A—N1A	27.98 (16)	C9B—C10B—C11B—C12B	−165.76 (16)
Pd1—Se1A—C8A—N2A	−156.51 (12)	C8A—N2A—C13A—C14A	−88.3 (2)
N2A—C9A—C10A—C11A	−176.73 (14)	C9A—N2A—C13A—C14A	89.43 (18)
N2B—C9B—C10B—C11B	−174.40 (14)	C15A—C14A—C13A—N2A	159.16 (14)
C7B—N1B—C8B—N2B	166.00 (16)	Pd1—O1B—C7B—N1B	5.8 (3)
C7B—N1B—C8B—Se1B	−18.5 (3)	Pd1—O1B—C7B—C1B	−178.88 (11)
C13B—N2B—C8B—N1B	−173.07 (15)	C8B—N1B—C7B—O1B	−1.3 (3)
C9B—N2B—C8B—N1B	4.0 (2)	C8B—N1B—C7B—C1B	−176.65 (16)
C13B—N2B—C8B—Se1B	10.8 (2)	C2B—C1B—C7B—O1B	166.87 (16)
C9B—N2B—C8B—Se1B	−172.10 (12)	C6B—C1B—C7B—O1B	−14.6 (2)
Pd1—Se1B—C8B—N1B	25.37 (17)	C2B—C1B—C7B—N1B	−17.0 (2)
Pd1—Se1B—C8B—N2B	−159.11 (12)	C6B—C1B—C7B—N1B	161.51 (16)
C13A—C14A—C15A—C16A	61.9 (2)	N2B—C13B—C14B—C15B	179.84 (15)
C4A—C3A—C2A—C1A	−1.3 (3)	C16B—C15B—C14B—C13B	172.77 (15)
C3B—C4B—C5B—C6B	0.4 (3)	C5B—C4B—C3B—C2B	0.9 (3)
C1B—C6B—C5B—C4B	−1.4 (3)	C1B—C2B—C3B—C4B	−1.3 (3)
C1A—C6A—C5A—C4A	−0.7 (3)	O1A—C7A—N1A—C8A	−9.0 (3)
Pd1—O1A—C7A—N1A	8.8 (3)	C1A—C7A—N1A—C8A	173.58 (16)
Pd1—O1A—C7A—C1A	−173.71 (11)	N2A—C8A—N1A—C7A	169.74 (16)
C8B—N2B—C13B—C14B	−94.0 (2)	Se1A—C8A—N1A—C7A	−14.7 (3)