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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107053711/sf3058sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107053711/sf3058Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107053711/sf3058IIsup3.hkl
Contains datablock II

CCDC references: 677072; 677073

Comment top

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 NiII and PdII 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 PdII 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 CO and CSe 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 CSe bond order of (I) on coordination to PdII 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 top

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).

Experimental top

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, 3JHH = 7.4 Hz, H12/H16), 0.99 (t, 3H, 3JHH = 7.4 Hz, H12/H16), 1.28 (m, 2H, 3JHH = 7.5 Hz, H11/H15), 1.45 (m, 2H, 3JHH = 7.5 Hz, H11/H15), 1.67 (q, 2H, 3JHH = 7.4 Hz, H10/H14), 1.83 (q, 2H, 3JHH = 7.4 Hz, H10/H14), 3.55 (t, 2H, 3JHH = 7.4 Hz, H9/H13), 4.08 (t, 2H, 3JHH = 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, 3JHH = 7.4 Hz, H12A/B or H16A/B), 0.98 (t, 6H, 3JHH = 7.4 Hz, H12A/B or H16A/B), 1.38 (m, 8H, 3JHH = 7.6 Hz, H11A/B, H15A/B), 1.67 (q, 4H, 3JHH = 7.7 Hz, H10A/B or H14A/B), 1.76 (q, 4H, 3JHH = 7.8 Hz, H10A/B or H14A/B), 3.78 (m, 8H, 3JHH = 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.

Refinement top

H atoms involved in hydrogen bonding were located in difference electron-density maps and restrained to N—H = 0.85 Å with Uiso(H) = 1.2Ueq(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 Uiso(H) = 1.2Ueq(C) for –CH2 and phenyl, or 1.5 Ueq(C) for –CH3.

Computing details top

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 top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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.]
[Figure 3] 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 top
Crystal data top
C16H24N2OSeF(000) = 704
Mr = 339.33Dx = 1.375 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2631 reflections
a = 10.3880 (17) Åθ = 2.4–27.2°
b = 15.715 (3) ŵ = 2.29 mm1
c = 10.1518 (16) ÅT = 273 K
β = 98.423 (3)°Block, yellow
V = 1639.4 (5) Å30.20 × 0.16 × 0.14 mm
Z = 4
Data collection top
Bruker APEX CCD area-detector
diffractometer
3775 independent reflections
Radiation source: fine-focus sealed tube3031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1113
Tmin = 0.651, Tmax = 0.732k = 2020
10228 measured reflectionsl = 913
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0423P)2]
where P = (Fo2 + 2Fc2)/3
3775 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C16H24N2OSeV = 1639.4 (5) Å3
Mr = 339.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3880 (17) ŵ = 2.29 mm1
b = 15.715 (3) ÅT = 273 K
c = 10.1518 (16) Å0.20 × 0.16 × 0.14 mm
β = 98.423 (3)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
3775 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
3031 reflections with I > 2σ(I)
Tmin = 0.651, Tmax = 0.732Rint = 0.038
10228 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.55 e Å3
3775 reflectionsΔρmin = 0.33 e Å3
187 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
xyzUiso*/Ueq
Se10.19333 (2)0.431363 (15)0.46477 (2)0.01660 (9)
O10.00770 (17)0.41704 (11)0.12025 (17)0.0192 (4)
C70.0657 (2)0.42323 (14)0.2242 (2)0.0147 (5)
N10.0293 (2)0.40125 (13)0.3469 (2)0.0157 (4)
N20.13174 (19)0.29950 (13)0.29734 (19)0.0160 (4)
C20.3013 (2)0.42633 (16)0.3311 (2)0.0187 (5)
H20.28140.39110.39890.022*
C80.0953 (2)0.37107 (15)0.3587 (2)0.0150 (5)
C110.1152 (3)0.12124 (16)0.2761 (3)0.0231 (6)
H11A0.16240.08640.34590.028*
H11B0.05730.08410.21850.028*
C120.2117 (3)0.16076 (17)0.1957 (3)0.0244 (6)
H12B0.26300.20250.24890.037*
H12A0.16540.18760.11780.037*
H12C0.26760.11730.16930.037*
C140.3490 (2)0.29865 (16)0.1623 (2)0.0192 (5)
H14B0.30590.28480.08650.023*
H14A0.35710.36010.16600.023*
C150.4839 (2)0.25914 (18)0.1427 (3)0.0253 (6)
H15B0.47590.19800.13320.030*
H15A0.52460.26980.22120.030*
C50.3607 (3)0.53127 (17)0.1294 (3)0.0256 (6)
H50.38130.56700.06250.031*
C130.2659 (2)0.26777 (16)0.2885 (2)0.0198 (5)
H13A0.30330.28720.36530.024*
H13B0.26510.20610.28960.024*
C10.2029 (2)0.45289 (15)0.2307 (2)0.0157 (5)
C40.4579 (3)0.50483 (17)0.2288 (3)0.0271 (6)
H40.54330.52230.22790.032*
C90.0438 (2)0.24274 (15)0.2357 (2)0.0182 (5)
H9A0.01530.27680.19200.022*
H9B0.09470.20770.16860.022*
C30.4282 (3)0.45243 (17)0.3297 (3)0.0235 (6)
H30.49360.43480.39660.028*
C60.2331 (3)0.50514 (15)0.1282 (2)0.0196 (5)
H60.16850.52220.06000.024*
C100.0342 (3)0.18581 (16)0.3390 (2)0.0213 (6)
H10A0.09120.22070.40110.026*
H10B0.02490.15610.38870.026*
C160.5707 (3)0.29393 (19)0.0215 (3)0.0268 (6)
H16C0.52940.28560.05620.040*
H16A0.58490.35360.03350.040*
H16B0.65260.26460.01040.040*
H10.062 (3)0.4321 (16)0.409 (3)0.015 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01405 (14)0.01869 (14)0.01733 (14)0.00070 (10)0.00318 (9)0.00252 (10)
O10.0197 (9)0.0215 (9)0.0154 (9)0.0010 (7)0.0007 (7)0.0010 (7)
C70.0161 (12)0.0119 (11)0.0160 (12)0.0031 (9)0.0022 (10)0.0006 (9)
N10.0156 (11)0.0186 (10)0.0125 (11)0.0028 (9)0.0010 (8)0.0030 (9)
N20.0161 (10)0.0172 (10)0.0140 (10)0.0014 (8)0.0001 (8)0.0008 (8)
C20.0193 (13)0.0222 (13)0.0149 (12)0.0014 (11)0.0032 (10)0.0023 (10)
C80.0144 (12)0.0182 (12)0.0117 (12)0.0011 (10)0.0000 (9)0.0024 (9)
C110.0246 (14)0.0181 (13)0.0254 (15)0.0033 (11)0.0002 (11)0.0051 (11)
C120.0216 (14)0.0260 (14)0.0255 (14)0.0029 (12)0.0029 (11)0.0011 (11)
C140.0179 (13)0.0234 (13)0.0162 (13)0.0009 (11)0.0020 (10)0.0013 (10)
C150.0227 (14)0.0294 (15)0.0221 (14)0.0069 (12)0.0020 (11)0.0022 (11)
C50.0288 (15)0.0225 (14)0.0279 (16)0.0047 (12)0.0117 (12)0.0018 (11)
C130.0204 (13)0.0189 (13)0.0196 (13)0.0046 (10)0.0014 (10)0.0010 (10)
C10.0160 (12)0.0140 (11)0.0173 (13)0.0023 (10)0.0034 (10)0.0039 (9)
C40.0180 (14)0.0286 (15)0.0363 (17)0.0047 (12)0.0095 (12)0.0079 (12)
C90.0206 (13)0.0165 (12)0.0166 (13)0.0007 (10)0.0002 (10)0.0038 (10)
C30.0166 (13)0.0292 (14)0.0240 (14)0.0025 (11)0.0008 (11)0.0071 (11)
C60.0238 (14)0.0187 (12)0.0168 (13)0.0030 (11)0.0046 (10)0.0002 (10)
C100.0237 (14)0.0226 (13)0.0176 (13)0.0012 (11)0.0036 (11)0.0023 (10)
C160.0209 (14)0.0376 (16)0.0210 (14)0.0050 (12)0.0003 (11)0.0030 (12)
Geometric parameters (Å, º) top
Se1—C81.848 (2)C14—H14A0.9700
O1—C71.212 (3)C15—C161.517 (4)
C7—N11.397 (3)C15—H15B0.9700
C7—C11.492 (3)C15—H15A0.9700
N1—C81.399 (3)C5—C41.383 (4)
N1—H10.83 (3)C5—C61.386 (4)
N2—C81.314 (3)C5—H50.9300
N2—C131.470 (3)C13—H13A0.9700
N2—C91.480 (3)C13—H13B0.9700
C2—C31.383 (4)C1—C61.397 (3)
C2—C11.397 (3)C4—C31.384 (4)
C2—H20.9300C4—H40.9300
C11—C121.515 (3)C9—C101.519 (3)
C11—C101.517 (3)C9—H9A0.9700
C11—H11A0.9700C9—H9B0.9700
C11—H11B0.9700C3—H30.9300
C12—H12B0.9600C6—H60.9300
C12—H12A0.9600C10—H10A0.9700
C12—H12C0.9600C10—H10B0.9700
C14—C131.516 (3)C16—H16C0.9600
C14—C151.520 (3)C16—H16A0.9600
C14—H14B0.9700C16—H16B0.9600
O1—C7—N1122.6 (2)C4—C5—C6120.8 (3)
O1—C7—C1122.6 (2)C4—C5—H5119.6
N1—C7—C1114.8 (2)C6—C5—H5119.6
C7—N1—C8122.3 (2)N2—C13—C14111.09 (19)
C7—N1—H1113.3 (18)N2—C13—H13A109.4
C8—N1—H1114.8 (18)C14—C13—H13A109.4
C8—N2—C13121.6 (2)N2—C13—H13B109.4
C8—N2—C9124.3 (2)C14—C13—H13B109.4
C13—N2—C9114.10 (19)H13A—C13—H13B108.0
C3—C2—C1120.0 (2)C6—C1—C2119.9 (2)
C3—C2—H2120.0C6—C1—C7117.9 (2)
C1—C2—H2120.0C2—C1—C7122.0 (2)
N2—C8—N1117.1 (2)C5—C4—C3120.1 (3)
N2—C8—Se1124.72 (18)C5—C4—H4120.0
N1—C8—Se1118.14 (17)C3—C4—H4120.0
C12—C11—C10113.8 (2)N2—C9—C10111.30 (19)
C12—C11—H11A108.8N2—C9—H9A109.4
C10—C11—H11A108.8C10—C9—H9A109.4
C12—C11—H11B108.8N2—C9—H9B109.4
C10—C11—H11B108.8C10—C9—H9B109.4
H11A—C11—H11B107.7H9A—C9—H9B108.0
C11—C12—H12B109.5C2—C3—C4120.0 (3)
C11—C12—H12A109.5C2—C3—H3120.0
H12B—C12—H12A109.5C4—C3—H3120.0
C11—C12—H12C109.5C5—C6—C1119.1 (2)
H12B—C12—H12C109.5C5—C6—H6120.5
H12A—C12—H12C109.5C1—C6—H6120.5
C13—C14—C15112.3 (2)C11—C10—C9112.1 (2)
C13—C14—H14B109.1C11—C10—H10A109.2
C15—C14—H14B109.1C9—C10—H10A109.2
C13—C14—H14A109.1C11—C10—H10B109.2
C15—C14—H14A109.1C9—C10—H10B109.2
H14B—C14—H14A107.9H10A—C10—H10B107.9
C16—C15—C14112.7 (2)C15—C16—H16C109.5
C16—C15—H15B109.0C15—C16—H16A109.5
C14—C15—H15B109.0H16C—C16—H16A109.5
C16—C15—H15A109.0C15—C16—H16B109.5
C14—C15—H15A109.0H16C—C16—H16B109.5
H15B—C15—H15A107.8H16A—C16—H16B109.5
O1—C7—N1—C80.5 (4)O1—C7—C1—C625.4 (3)
C1—C7—N1—C8179.1 (2)N1—C7—C1—C6156.0 (2)
C13—N2—C8—N1172.0 (2)O1—C7—C1—C2151.1 (2)
C9—N2—C8—N110.1 (3)N1—C7—C1—C227.5 (3)
C13—N2—C8—Se110.9 (3)C6—C5—C4—C30.8 (4)
C9—N2—C8—Se1166.99 (17)C8—N2—C9—C1081.4 (3)
C7—N1—C8—N261.6 (3)C13—N2—C9—C1096.7 (2)
C7—N1—C8—Se1121.1 (2)C1—C2—C3—C40.1 (4)
C13—C14—C15—C16176.3 (2)C5—C4—C3—C20.1 (4)
C8—N2—C13—C1492.0 (3)C4—C5—C6—C11.4 (4)
C9—N2—C13—C1489.9 (2)C2—C1—C6—C51.3 (4)
C15—C14—C13—N2173.7 (2)C7—C1—C6—C5177.9 (2)
C3—C2—C1—C60.6 (4)C12—C11—C10—C958.9 (3)
C3—C2—C1—C7177.1 (2)N2—C9—C10—C11174.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Se1i0.83 (3)2.76 (3)3.539 (2)159 (2)
C6—H6···O1ii0.932.483.407 (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) top
Crystal data top
[Pd(C16H23N2OSe)2]Z = 2
Mr = 783.05F(000) = 792
Triclinic, P1Dx = 1.593 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9302 (8) ÅCell parameters from 6089 reflections
b = 10.9315 (9) Åθ = 2.5–28.1°
c = 15.4119 (13) ŵ = 2.83 mm1
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) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer
7329 independent reflections
Radiation source: fine-focus sealed tube6802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1313
Tmin = 0.785, Tmax = 0.797k = 1413
18809 measured reflectionsl = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0306P)2 + 0.7045P]
where P = (Fo2 + 2Fc2)/3
7329 reflections(Δ/σ)max = 0.001
374 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
[Pd(C16H23N2OSe)2]γ = 81.867 (1)°
Mr = 783.05V = 1632.0 (2) Å3
Triclinic, P1Z = 2
a = 9.9302 (8) ÅMo Kα radiation
b = 10.9315 (9) ŵ = 2.83 mm1
c = 15.4119 (13) ÅT = 173 K
α = 80.216 (1)°0.09 × 0.08 × 0.08 mm
β = 88.291 (1)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
7329 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
6802 reflections with I > 2σ(I)
Tmin = 0.785, Tmax = 0.797Rint = 0.017
18809 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.05Δρmax = 0.55 e Å3
7329 reflectionsΔρmin = 0.38 e Å3
374 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
xyzUiso*/Ueq
Pd10.770245 (12)0.454364 (12)0.247821 (8)0.01375 (4)
Se1A0.547248 (17)0.556941 (16)0.222043 (11)0.01692 (5)
Se1B0.817164 (18)0.632990 (16)0.299743 (12)0.01941 (5)
O1B0.96158 (13)0.36044 (12)0.27371 (9)0.0201 (3)
O1A0.73153 (13)0.29951 (12)0.20070 (8)0.0194 (3)
N2A0.37899 (14)0.53175 (13)0.08718 (9)0.0146 (3)
C9B1.14223 (18)0.61760 (17)0.46837 (11)0.0163 (3)
H13A1.17550.52680.47440.020*
H13B1.13020.63880.52830.020*
N1B1.07650 (14)0.48060 (14)0.35262 (9)0.0147 (3)
N2B1.00896 (14)0.64422 (13)0.42335 (9)0.0147 (3)
C9A0.30972 (17)0.46624 (17)0.02896 (11)0.0157 (3)
H9AA0.37690.40260.00700.019*
H9AB0.27250.52740.02250.019*
C8A0.48186 (17)0.46962 (16)0.13838 (11)0.0143 (3)
C10A0.19479 (17)0.40237 (17)0.07591 (11)0.0169 (3)
H10A0.23100.34470.12930.020*
H11B0.12490.46660.09490.020*
C10B1.24854 (17)0.69094 (17)0.41918 (11)0.0176 (4)
H12A1.22020.78170.41850.021*
H12B1.25460.67630.35750.021*
C8B0.98127 (17)0.57589 (16)0.36358 (11)0.0145 (3)
C2B1.31349 (18)0.31619 (18)0.33731 (11)0.0184 (4)
H2B1.32200.39700.34970.022*
C14A0.21303 (18)0.68508 (17)0.15592 (11)0.0180 (4)
H15A0.12570.67050.13290.022*
H15B0.23410.62390.21060.022*
C3A0.5343 (2)0.02689 (18)0.10928 (12)0.0224 (4)
H3A0.45690.05740.09070.027*
C15A0.1986 (2)0.81801 (18)0.17714 (12)0.0223 (4)
H17A0.12900.82550.22400.027*
H17B0.28610.83110.20080.027*
C6B1.17617 (18)0.17012 (17)0.29705 (11)0.0183 (4)
H6B1.09080.15150.28060.022*
C4B1.41481 (19)0.10644 (19)0.32571 (12)0.0230 (4)
H4B1.49240.04400.32980.028*
C6A0.76049 (18)0.06160 (17)0.16393 (11)0.0176 (3)
H6A0.83820.09160.18250.021*
C2A0.52651 (18)0.09833 (17)0.11778 (12)0.0187 (4)
H2A0.44440.15360.10390.022*
C5B1.28965 (19)0.07855 (18)0.30357 (12)0.0217 (4)
H5B1.28140.00310.29280.026*
C5A0.76796 (19)0.06295 (17)0.15395 (12)0.0208 (4)
H5A0.85100.11780.16510.025*
C7A0.63071 (17)0.27561 (16)0.16131 (10)0.0143 (3)
C16B0.8200 (2)1.10473 (18)0.40251 (13)0.0255 (4)
H25A0.90981.12360.41620.038*
H25B0.74931.15910.42900.038*
H25C0.80811.11940.33850.038*
C13B0.91040 (18)0.74404 (16)0.45145 (11)0.0172 (3)
H26A0.92390.74300.51500.021*
H26B0.81770.72380.44450.021*
C12A0.00536 (19)0.27661 (19)0.06108 (13)0.0244 (4)
H27A0.03240.22160.11670.037*
H27B0.03300.22870.02200.037*
H27C0.06310.34580.07280.037*
C1B1.18762 (17)0.28944 (17)0.31464 (10)0.0152 (3)
C1A0.63908 (17)0.14309 (16)0.14675 (10)0.0146 (3)
C4A0.6543 (2)0.10739 (17)0.12768 (12)0.0219 (4)
H4A0.65880.19320.12230.026*
C11A0.12917 (19)0.32892 (19)0.01731 (12)0.0225 (4)
H31A0.10150.38440.03880.027*
H31B0.19660.25900.00350.027*
C11B1.38801 (18)0.65209 (19)0.46216 (13)0.0231 (4)
H32A1.37740.64590.52680.028*
H32B1.42620.56810.44970.028*
C13A0.32587 (17)0.66404 (16)0.08770 (11)0.0166 (3)
H33A0.29010.70190.02850.020*
H33B0.40190.70850.09940.020*
C15B0.80887 (19)0.96858 (18)0.43930 (13)0.0227 (4)
H34A0.71780.95050.42540.027*
H34B0.81690.95560.50420.027*
C16A0.1590 (2)0.92151 (19)0.09893 (13)0.0271 (4)
H35A0.22590.91380.05140.041*
H35B0.15691.00340.11710.041*
H35C0.06890.91380.07800.041*
C7B1.06315 (17)0.38560 (16)0.31088 (11)0.0149 (3)
C14B0.91719 (18)0.87620 (16)0.40298 (11)0.0175 (3)
H38A0.90210.87990.33930.021*
H38B1.00850.89940.41030.021*
C3B1.42681 (19)0.22501 (19)0.34190 (12)0.0226 (4)
H3B1.51300.24420.35620.027*
C12B1.4869 (2)0.7439 (2)0.42947 (15)0.0349 (5)
H40A1.49560.75240.36530.052*
H40B1.57600.71280.45640.052*
H40C1.45290.82570.44560.052*
N1A0.52080 (14)0.35107 (14)0.12834 (9)0.0151 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01128 (7)0.01286 (7)0.01776 (7)0.00194 (5)0.00408 (5)0.00350 (5)
Se1A0.01248 (9)0.01599 (9)0.02368 (9)0.00062 (6)0.00464 (7)0.00762 (7)
Se1B0.01574 (9)0.01337 (9)0.02999 (10)0.00011 (6)0.00997 (7)0.00614 (7)
O1B0.0150 (6)0.0183 (6)0.0285 (7)0.0003 (5)0.0069 (5)0.0090 (5)
O1A0.0146 (6)0.0170 (6)0.0282 (7)0.0010 (5)0.0069 (5)0.0081 (5)
N2A0.0122 (7)0.0149 (7)0.0168 (7)0.0030 (5)0.0010 (5)0.0023 (6)
C9B0.0168 (8)0.0167 (8)0.0160 (8)0.0036 (6)0.0051 (6)0.0026 (6)
N1B0.0125 (7)0.0168 (7)0.0155 (6)0.0035 (5)0.0011 (5)0.0032 (6)
N2B0.0136 (7)0.0132 (7)0.0177 (7)0.0023 (5)0.0016 (5)0.0029 (5)
C9A0.0134 (8)0.0197 (9)0.0144 (7)0.0025 (6)0.0037 (6)0.0034 (7)
C8A0.0111 (8)0.0174 (8)0.0150 (7)0.0051 (6)0.0012 (6)0.0024 (6)
C10A0.0132 (8)0.0204 (9)0.0183 (8)0.0046 (7)0.0000 (6)0.0050 (7)
C10B0.0125 (8)0.0206 (9)0.0193 (8)0.0013 (7)0.0026 (6)0.0024 (7)
C8B0.0136 (8)0.0150 (8)0.0149 (7)0.0052 (6)0.0024 (6)0.0009 (6)
C2B0.0171 (9)0.0207 (9)0.0183 (8)0.0027 (7)0.0007 (7)0.0056 (7)
C14A0.0166 (8)0.0181 (9)0.0188 (8)0.0017 (7)0.0002 (7)0.0028 (7)
C3A0.0237 (10)0.0217 (10)0.0251 (9)0.0097 (7)0.0017 (7)0.0077 (7)
C15A0.0243 (10)0.0224 (10)0.0209 (8)0.0006 (8)0.0006 (7)0.0076 (7)
C6B0.0182 (9)0.0194 (9)0.0177 (8)0.0020 (7)0.0015 (7)0.0049 (7)
C4B0.0196 (9)0.0265 (10)0.0199 (8)0.0059 (7)0.0004 (7)0.0035 (7)
C6A0.0169 (8)0.0180 (9)0.0183 (8)0.0032 (7)0.0009 (7)0.0032 (7)
C2A0.0184 (9)0.0169 (9)0.0214 (8)0.0031 (7)0.0019 (7)0.0044 (7)
C5B0.0246 (10)0.0200 (9)0.0197 (8)0.0018 (7)0.0000 (7)0.0054 (7)
C5A0.0222 (9)0.0166 (9)0.0221 (9)0.0003 (7)0.0010 (7)0.0019 (7)
C7A0.0146 (8)0.0160 (8)0.0131 (7)0.0044 (6)0.0013 (6)0.0029 (6)
C16B0.0289 (10)0.0205 (10)0.0264 (9)0.0049 (8)0.0038 (8)0.0086 (8)
C13B0.0172 (8)0.0168 (9)0.0187 (8)0.0029 (7)0.0017 (7)0.0064 (7)
C12A0.0198 (9)0.0264 (10)0.0283 (10)0.0082 (8)0.0057 (8)0.0038 (8)
C1B0.0140 (8)0.0189 (9)0.0120 (7)0.0008 (6)0.0002 (6)0.0017 (6)
C1A0.0169 (8)0.0142 (8)0.0130 (7)0.0036 (6)0.0005 (6)0.0019 (6)
C4A0.0303 (10)0.0141 (9)0.0225 (9)0.0066 (7)0.0043 (8)0.0041 (7)
C11A0.0213 (9)0.0273 (10)0.0213 (9)0.0081 (8)0.0022 (7)0.0069 (8)
C11B0.0159 (9)0.0258 (10)0.0278 (9)0.0039 (7)0.0066 (7)0.0091 (8)
C13A0.0153 (8)0.0142 (8)0.0189 (8)0.0007 (6)0.0022 (6)0.0002 (7)
C15B0.0186 (9)0.0221 (10)0.0273 (9)0.0014 (7)0.0015 (7)0.0074 (8)
C16A0.0286 (10)0.0209 (10)0.0311 (10)0.0019 (8)0.0040 (8)0.0058 (8)
C7B0.0149 (8)0.0153 (8)0.0138 (7)0.0020 (6)0.0002 (6)0.0002 (6)
C14B0.0163 (8)0.0161 (9)0.0199 (8)0.0003 (7)0.0003 (7)0.0041 (7)
C3B0.0143 (9)0.0319 (11)0.0210 (9)0.0002 (7)0.0013 (7)0.0054 (8)
C12B0.0165 (10)0.0572 (15)0.0344 (11)0.0103 (9)0.0010 (8)0.0130 (10)
N1A0.0130 (7)0.0155 (7)0.0169 (7)0.0032 (5)0.0027 (5)0.0019 (6)
Geometric parameters (Å, º) top
Pd1—O1A2.0395 (12)C4B—C3B1.383 (3)
Pd1—O1B2.0439 (12)C4B—C5B1.386 (3)
Pd1—Se1B2.3411 (3)C4B—H4B0.9500
Pd1—Se1A2.3489 (3)C6A—C5A1.387 (3)
Se1A—C8A1.9076 (17)C6A—C1A1.397 (2)
Se1B—C8B1.9006 (16)C6A—H6A0.9500
O1B—C7B1.260 (2)C2A—C1A1.395 (2)
O1A—C7A1.266 (2)C2A—H2A0.9500
N2A—C8A1.341 (2)C5B—H5B0.9500
N2A—C13A1.469 (2)C5A—C4A1.387 (3)
N2A—C9A1.478 (2)C5A—H5A0.9500
C9B—N2B1.481 (2)C7A—N1A1.329 (2)
C9B—C10B1.522 (3)C7A—C1A1.494 (2)
C9B—H13A0.9900C16B—C15B1.518 (3)
C9B—H13B0.9900C16B—H25A0.9800
N1B—C8B1.334 (2)C16B—H25B0.9800
N1B—C7B1.335 (2)C16B—H25C0.9800
N2B—C8B1.338 (2)C13B—C14B1.519 (2)
N2B—C13B1.473 (2)C13B—H26A0.9900
C9A—C10A1.523 (2)C13B—H26B0.9900
C9A—H9AA0.9900C12A—C11A1.521 (3)
C9A—H9AB0.9900C12A—H27A0.9800
C8A—N1A1.333 (2)C12A—H27B0.9800
C10A—C11A1.521 (2)C12A—H27C0.9800
C10A—H10A0.9900C1B—C7B1.501 (2)
C10A—H11B0.9900C4A—H4A0.9500
C10B—C11B1.526 (2)C11A—H31A0.9900
C10B—H12A0.9900C11A—H31B0.9900
C10B—H12B0.9900C11B—C12B1.517 (3)
C2B—C3B1.389 (2)C11B—H32A0.9900
C2B—C1B1.391 (2)C11B—H32B0.9900
C2B—H2B0.9500C13A—H33A0.9900
C14A—C15A1.529 (3)C13A—H33B0.9900
C14A—C13A1.534 (2)C15B—C14B1.529 (2)
C14A—H15A0.9900C15B—H34A0.9900
C14A—H15B0.9900C15B—H34B0.9900
C3A—C4A1.383 (3)C16A—H35A0.9800
C3A—C2A1.388 (3)C16A—H35B0.9800
C3A—H3A0.9500C16A—H35C0.9800
C15A—C16A1.525 (3)C14B—H38A0.9900
C15A—H17A0.9900C14B—H38B0.9900
C15A—H17B0.9900C3B—H3B0.9500
C6B—C5B1.391 (2)C12B—H40A0.9800
C6B—C1B1.397 (3)C12B—H40B0.9800
C6B—H6B0.9500C12B—H40C0.9800
O1A—Pd1—O1B86.08 (5)C4A—C5A—H5A120.0
O1A—Pd1—Se1B178.98 (4)C6A—C5A—H5A120.0
O1B—Pd1—Se1B93.59 (4)O1A—C7A—N1A130.00 (16)
O1A—Pd1—Se1A93.12 (3)O1A—C7A—C1A114.96 (14)
O1B—Pd1—Se1A177.91 (4)N1A—C7A—C1A115.00 (15)
Se1B—Pd1—Se1A87.244 (8)C15B—C16B—H25A109.5
C8A—Se1A—Pd1102.73 (5)C15B—C16B—H25B109.5
C8B—Se1B—Pd1103.40 (5)H25A—C16B—H25B109.5
C7B—O1B—Pd1132.90 (12)C15B—C16B—H25C109.5
C7A—O1A—Pd1132.89 (11)H25A—C16B—H25C109.5
C8A—N2A—C13A123.06 (14)H25B—C16B—H25C109.5
C8A—N2A—C9A120.23 (14)N2B—C13B—C14B116.20 (15)
C13A—N2A—C9A116.67 (13)N2B—C13B—H26A108.2
N2B—C9B—C10B112.65 (14)C14B—C13B—H26A108.2
N2B—C9B—H13A109.1N2B—C13B—H26B108.2
C10B—C9B—H13A109.1C14B—C13B—H26B108.2
N2B—C9B—H13B109.1H26A—C13B—H26B107.4
C10B—C9B—H13B109.1C11A—C12A—H27A109.5
H13A—C9B—H13B107.8C11A—C12A—H27B109.5
C8B—N1B—C7B127.02 (15)H27A—C12A—H27B109.5
C8B—N2B—C13B123.47 (14)C11A—C12A—H27C109.5
C8B—N2B—C9B120.27 (14)H27A—C12A—H27C109.5
C13B—N2B—C9B116.21 (14)H27B—C12A—H27C109.5
N2A—C9A—C10A112.28 (14)C2B—C1B—C6B119.47 (16)
N2A—C9A—H9AA109.1C2B—C1B—C7B121.12 (16)
C10A—C9A—H9AA109.1C6B—C1B—C7B119.40 (16)
N2A—C9A—H9AB109.1C2A—C1A—C6A119.23 (16)
C10A—C9A—H9AB109.1C2A—C1A—C7A121.03 (15)
H9AA—C9A—H9AB107.9C6A—C1A—C7A119.73 (15)
N1A—C8A—N2A115.79 (15)C3A—C4A—C5A120.04 (17)
N1A—C8A—Se1A127.55 (12)C3A—C4A—H4A120.0
N2A—C8A—Se1A116.52 (12)C5A—C4A—H4A120.0
C11A—C10A—C9A112.05 (15)C12A—C11A—C10A111.80 (15)
C11A—C10A—H10A109.2C12A—C11A—H31A109.3
C9A—C10A—H10A109.2C10A—C11A—H31A109.3
C11A—C10A—H11B109.2C12A—C11A—H31B109.3
C9A—C10A—H11B109.2C10A—C11A—H31B109.3
H10A—C10A—H11B107.9H31A—C11A—H31B107.9
C9B—C10B—C11B111.40 (15)C12B—C11B—C10B112.47 (16)
C9B—C10B—H12A109.3C12B—C11B—H32A109.1
C11B—C10B—H12A109.3C10B—C11B—H32A109.1
C9B—C10B—H12B109.3C12B—C11B—H32B109.1
C11B—C10B—H12B109.3C10B—C11B—H32B109.1
H12A—C10B—H12B108.0H32A—C11B—H32B107.8
N1B—C8B—N2B115.72 (14)N2A—C13A—C14A114.31 (14)
N1B—C8B—Se1B128.10 (13)N2A—C13A—H33A108.7
N2B—C8B—Se1B116.04 (12)C14A—C13A—H33A108.7
C3B—C2B—C1B120.11 (17)N2A—C13A—H33B108.7
C3B—C2B—H2B119.9C14A—C13A—H33B108.7
C1B—C2B—H2B119.9H33A—C13A—H33B107.6
C15A—C14A—C13A111.52 (15)C16B—C15B—C14B113.35 (16)
C15A—C14A—H15A109.3C16B—C15B—H34A108.9
C13A—C14A—H15A109.3C14B—C15B—H34A108.9
C15A—C14A—H15B109.3C16B—C15B—H34B108.9
C13A—C14A—H15B109.3C14B—C15B—H34B108.9
H15A—C14A—H15B108.0H34A—C15B—H34B107.7
C4A—C3A—C2A120.31 (17)C15A—C16A—H35A109.5
C4A—C3A—H3A119.8C15A—C16A—H35B109.5
C2A—C3A—H3A119.8H35A—C16A—H35B109.5
C16A—C15A—C14A114.54 (15)C15A—C16A—H35C109.5
C16A—C15A—H17A108.6H35A—C16A—H35C109.5
C14A—C15A—H17A108.6H35B—C16A—H35C109.5
C16A—C15A—H17B108.6O1B—C7B—N1B130.59 (16)
C14A—C15A—H17B108.6O1B—C7B—C1B115.43 (15)
H17A—C15A—H17B107.6N1B—C7B—C1B113.84 (15)
C5B—C6B—C1B120.04 (17)C13B—C14B—C15B109.94 (15)
C5B—C6B—H6B120.0C13B—C14B—H38A109.7
C1B—C6B—H6B120.0C15B—C14B—H38A109.7
C3B—C4B—C5B120.05 (17)C13B—C14B—H38B109.7
C3B—C4B—H4B120.0C15B—C14B—H38B109.7
C5B—C4B—H4B120.0H38A—C14B—H38B108.2
C5A—C6A—C1A120.27 (17)C4B—C3B—C2B120.30 (18)
C5A—C6A—H6A119.9C4B—C3B—H3B119.8
C1A—C6A—H6A119.9C2B—C3B—H3B119.8
C3A—C2A—C1A120.08 (16)C11B—C12B—H40A109.5
C3A—C2A—H2A120.0C11B—C12B—H40B109.5
C1A—C2A—H2A120.0H40A—C12B—H40B109.5
C4B—C5B—C6B120.01 (18)C11B—C12B—H40C109.5
C4B—C5B—H5B120.0H40A—C12B—H40C109.5
C6B—C5B—H5B120.0H40B—C12B—H40C109.5
C4A—C5A—C6A120.03 (17)C7A—N1A—C8A127.50 (15)
O1A—Pd1—Se1A—C8A19.43 (6)C9B—N2B—C13B—C14B88.86 (18)
Se1B—Pd1—Se1A—C8A159.62 (5)C3B—C2B—C1B—C6B0.3 (3)
O1B—Pd1—Se1B—C8B15.02 (7)C3B—C2B—C1B—C7B178.85 (16)
Se1A—Pd1—Se1B—C8B163.06 (5)C5B—C6B—C1B—C2B1.0 (3)
O1A—Pd1—O1B—C7B175.66 (17)C5B—C6B—C1B—C7B177.55 (16)
Se1B—Pd1—O1B—C7B5.30 (16)C3A—C2A—C1A—C6A2.3 (3)
O1B—Pd1—O1A—C7A173.48 (16)C3A—C2A—C1A—C7A176.48 (16)
Se1A—Pd1—O1A—C7A8.45 (16)C5A—C6A—C1A—C2A1.3 (3)
C10B—C9B—N2B—C8B89.66 (19)C5A—C6A—C1A—C7A177.48 (16)
C10B—C9B—N2B—C13B93.06 (18)O1A—C7A—C1A—C2A169.17 (16)
C8A—N2A—C9A—C10A86.64 (19)N1A—C7A—C1A—C2A13.0 (2)
C13A—N2A—C9A—C10A91.15 (17)O1A—C7A—C1A—C6A9.6 (2)
C13A—N2A—C8A—N1A178.13 (15)N1A—C7A—C1A—C6A168.28 (16)
C9A—N2A—C8A—N1A4.2 (2)C2A—C3A—C4A—C5A0.6 (3)
C13A—N2A—C8A—Se1A5.8 (2)C6A—C5A—C4A—C3A1.6 (3)
C9A—N2A—C8A—Se1A171.82 (12)C9A—C10A—C11A—C12A174.11 (15)
Pd1—Se1A—C8A—N1A27.98 (16)C9B—C10B—C11B—C12B165.76 (16)
Pd1—Se1A—C8A—N2A156.51 (12)C8A—N2A—C13A—C14A88.3 (2)
N2A—C9A—C10A—C11A176.73 (14)C9A—N2A—C13A—C14A89.43 (18)
N2B—C9B—C10B—C11B174.40 (14)C15A—C14A—C13A—N2A159.16 (14)
C7B—N1B—C8B—N2B166.00 (16)Pd1—O1B—C7B—N1B5.8 (3)
C7B—N1B—C8B—Se1B18.5 (3)Pd1—O1B—C7B—C1B178.88 (11)
C13B—N2B—C8B—N1B173.07 (15)C8B—N1B—C7B—O1B1.3 (3)
C9B—N2B—C8B—N1B4.0 (2)C8B—N1B—C7B—C1B176.65 (16)
C13B—N2B—C8B—Se1B10.8 (2)C2B—C1B—C7B—O1B166.87 (16)
C9B—N2B—C8B—Se1B172.10 (12)C6B—C1B—C7B—O1B14.6 (2)
Pd1—Se1B—C8B—N1B25.37 (17)C2B—C1B—C7B—N1B17.0 (2)
Pd1—Se1B—C8B—N2B159.11 (12)C6B—C1B—C7B—N1B161.51 (16)
C13A—C14A—C15A—C16A61.9 (2)N2B—C13B—C14B—C15B179.84 (15)
C4A—C3A—C2A—C1A1.3 (3)C16B—C15B—C14B—C13B172.77 (15)
C3B—C4B—C5B—C6B0.4 (3)C5B—C4B—C3B—C2B0.9 (3)
C1B—C6B—C5B—C4B1.4 (3)C1B—C2B—C3B—C4B1.3 (3)
C1A—C6A—C5A—C4A0.7 (3)O1A—C7A—N1A—C8A9.0 (3)
Pd1—O1A—C7A—N1A8.8 (3)C1A—C7A—N1A—C8A173.58 (16)
Pd1—O1A—C7A—C1A173.71 (11)N2A—C8A—N1A—C7A169.74 (16)
C8B—N2B—C13B—C14B94.0 (2)Se1A—C8A—N1A—C7A14.7 (3)

Experimental details

(I)(II)
Crystal data
Chemical formulaC16H24N2OSe[Pd(C16H23N2OSe)2]
Mr339.33783.05
Crystal system, space groupMonoclinic, P21/cTriclinic, P1
Temperature (K)273173
a, b, c (Å)10.3880 (17), 15.715 (3), 10.1518 (16)9.9302 (8), 10.9315 (9), 15.4119 (13)
α, β, γ (°)90, 98.423 (3), 9080.216 (1), 88.291 (1), 81.867 (1)
V3)1639.4 (5)1632.0 (2)
Z42
Radiation typeMo KαMo Kα
µ (mm1)2.292.83
Crystal size (mm)0.20 × 0.16 × 0.140.09 × 0.08 × 0.08
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Bruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Multi-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.651, 0.7320.785, 0.797
No. of measured, independent and
observed [I > 2σ(I)] reflections
10228, 3775, 3031 18809, 7329, 6802
Rint0.0380.017
(sin θ/λ)max1)0.6660.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.085, 1.03 0.022, 0.056, 1.05
No. of reflections37757329
No. of parameters187374
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.330.55, 0.38

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001).

Selected bond lengths (Å) for (I) top
Se1—C81.848 (2)N1—H10.83 (3)
O1—C71.212 (3)N2—C81.314 (3)
C7—N11.397 (3)N2—C131.470 (3)
C7—C11.492 (3)N2—C91.480 (3)
N1—C81.399 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Se1i0.83 (3)2.76 (3)3.539 (2)159 (2)
C6—H6···O1ii0.932.483.407 (3)173.8
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z.
Selected bond lengths (Å) for (II) top
Pd1—O1A2.0395 (12)N2A—C13A1.469 (2)
Pd1—O1B2.0439 (12)N2A—C9A1.478 (2)
Pd1—Se1B2.3411 (3)C9B—N2B1.481 (2)
Pd1—Se1A2.3489 (3)N1B—C8B1.334 (2)
Se1A—C8A1.9076 (17)N1B—C7B1.335 (2)
Se1B—C8B1.9006 (16)N2B—C8B1.338 (2)
O1B—C7B1.260 (2)N2B—C13B1.473 (2)
O1A—C7A1.266 (2)C8A—N1A1.333 (2)
N2A—C8A1.341 (2)C7A—N1A1.329 (2)
 

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