metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Pages m261-m262

(S)-α-Benzyl­prolinium cis-[(S)-α-benzyl­prolinato]di­chloridopalladium(II)

aDepartment of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA
*Correspondence e-mail: dhobart@vt.edu

(Received 2 April 2013; accepted 8 April 2013; online 13 April 2013)

The title complex salt, (C12H16NO2)[PdCl2(C12H14NO2)], is of inter­est with respect to organic and organometallic catalysis. The compound crystallizes as very small orange–red irregular prisms and the asymmetric unit contains three crystallographically distinct cation–anion pairs. The coordination geometry about the palladium atoms is square-planar with the chloride ligands cis to one another. The structure displays N—H⋯Cl and O—H⋯O hydrogen bonding such that the N—H⋯Cl hydrogen bonds align the cation–anion pairs in a linear fashion along [001], with the O—H⋯O hydrogen bonds connecting these linear strands along [100] and [010].

Related literature

For the use of benzyl­proline in organocatalysis, see: Sutar & Joshi (2013[Sutar, R. L. & Joshi, N. N. (2013). Tetrahedron Asymmetry, 24, 43-49.]); Cordova et al. (2004[Cordova, A., Sunden, H., Engqvist, M., Ibrahem, I. & Casas, J. (2004). J. Am. Chem. Soc. 126, 8914-8915.]); Rispens et al. (1995[Rispens, M. T., Zondervan, C. & Feringa, B. L. (1995). Tetrahedron Asymmetry, 6, 661-664.]). For other mono-amino acid halide complexes of palladium(II), see: Akat'eva et al. (2004[Akat'eva, M. E., Erofeeva, O. S., Dobrynina, N. A., Ivanova, N. A. & Efimenko, I. A. (2004). Russ. J. Coord. Chem. 30, 584-590.]); Asanin et al. (2004[Asanin, D. P., Rajkovic, S., Molnar-Gabor, D. & Djuran, M. I. (2004). Monatsh. Chem. 135, 1445-1453.]); Chernova et al. (1976[Chernova, N. N., Shakhova, L. P. & Kukushkin, Y. N. (1976). Zh. Neorg. Khim. 21, 3027-3030.], 1978[Chernova, N. N., Kurskii, I. G., Vashchenko, L. P. & Ivanchenko, O. N. (1978). Zh. Neorg. Khim. 23, 1314-1318.]); Djuran & Milinkovic (1999[Djuran, M. I. & Milinkovic, S. U. (1999). Polyhedron, 18, 3611-3616.], 2000[Djuran, M. I. & Milinkovic, S. U. (2000). Polyhedron, 19, 959-963.]); Faraglia et al. (1997[Faraglia, G., Fregona, D. & Sitran, S. (1997). Transition Met. Chem. 22, 492-496.]); Hao et al. (2007[Hao, Y.-Z., Li, Z.-X. & Tian, J.-L. (2007). J. Mol. Catal. A Chem. 265, 258-267.], 2009[Hao, Y.-Z., Zhang, Y.-L., Wang, L.-H. & Ju, X.-Y. (2009). Open Catal. J. 2, 66-70.]); Krylova et al. (1994[Krylova, L. F., Dikanskaya, L. D. & Fedotov, M. A. (1994). Koord. Khim. 20, 57-59.]); Spacu & Ungureanu-Vicol (1966[Spacu, P. & Ungureanu-Vicol, O. (1966). An. Univ. Bucuresti Ser. Stiint. Natur. 15, 109-118.]); Vicol & Harabor (1974[Vicol, O. & Harabor, P. (1974). An. Stiint. Univ. Al. I. Cuza Iasi Sect. 1c, 20, 117-123.]).

[Scheme 1]

Experimental

Crystal data
  • (C12H16NO2)[PdCl2(C12H14NO2)]

  • Mr = 587.80

  • Triclinic, P 1

  • a = 10.6095 (5) Å

  • b = 12.3870 (4) Å

  • c = 14.6878 (4) Å

  • α = 101.376 (3)°

  • β = 93.421 (3)°

  • γ = 101.996 (3)°

  • V = 1840.80 (11) Å3

  • Z = 3

  • Mo Kα radiation

  • μ = 1.01 mm−1

  • T = 100 K

  • 0.19 × 0.12 × 0.11 mm

Data collection
  • Oxford Diffraction Gemini Ultra diffractometer

  • Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]) Tmin = 0.884, Tmax = 0.929

  • 40995 measured reflections

  • 23898 independent reflections

  • 21552 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.082

  • S = 1.03

  • 23898 reflections

  • 895 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 1.99 e Å−3

  • Δρmin = −0.77 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 11561 Friedel pairs

  • Flack parameter: −0.039 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4⋯O2i 0.84 1.69 2.521 (3) 171
O8—H8A⋯O6ii 0.84 1.71 2.547 (3) 171
O12—H12A⋯O10iii 0.84 1.73 2.565 (3) 177
N1—H1⋯Cl3 0.93 2.46 3.334 (3) 156
N2—H2C⋯Cl6iv 0.92 2.45 3.249 (3) 145
N3—H3⋯Cl2 0.93 2.48 3.354 (3) 156
N4—H4A⋯Cl3 0.92 2.35 3.216 (3) 156
N5—H5⋯Cl4 0.93 2.44 3.319 (3) 159
N6—H6D⋯Cl1v 0.92 2.37 3.235 (3) 156
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z-1; (v) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

The title compound was isolated as a minor product from a reaction mixture of palladium(II) acetate and S-(α)-benzylproline hydrochloride. The expected product was the bis-amino acid palladium(II) chelate and was indeed formed in good yield. Attempts to crystallize the expected product were successful, however in every instance very small orange-red crystals of the title compound were observed to form along with the expected product.

Related literature top

For the use of benzylproline in organocatalysis, see: Sutar & Joshi (2013); Cordova et al. (2004); Rispens et al. (1995). For other mono-amino acid halide complexes of palladium(II), see: Akat'eva et al. (2004); Asanin et al. (2004); Chernova et al. (1976, 1978); Djuran & Milinkovic (1999, 2000); Faraglia et al. (1997); Hao et al. (2007, 2009); Krylova et al. (1994); Spacu & Ungureanu-Vicol (1966); Vicol & Harabor (1974).

Experimental top

The title compound was isolated as one of two products from a reaction mixture of 0.22 mmol palladium(II) acetate and 0.49 mmol S-(a)-benzylproline hydrochloride in 3 ml of 50/50 (v/v) acetone/water. Single crystals suitable for diffraction were grown via slow evaporation from a 50/50 (v/v) solution of acetone and water.

Refinement top

Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. A view of a single cation/anion pair of the title compound showing atom labels. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the unit cell contents of the title compound along [100] showing displacement ellipsoids at the 50% probability level.
[Figure 3] Fig. 3. A view of a section of the crystal packing diagram of the title compound along [010] showing N1–H1···Cl3i, N3–H3···Cl2ii, N4–H4A···Cl3iii, and N5–H5···Cl4iv hydrogen bonds [Symmetry codes: (i) -1+x, -1+y, +z; (ii) -1+x, -1+y, +z; (iii) -1+x, -1+y, +z; (iv)-1+x, -1+y, +z].
(S)-α-Benzylprolinium cis-[(S)-α-benzylprolinato]dichloridopalladium(II) top
Crystal data top
(C12H16NO2)[PdCl2(C12H14NO2)]Z = 3
Mr = 587.80F(000) = 900
Triclinic, P1Dx = 1.591 Mg m3
a = 10.6095 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3870 (4) ÅCell parameters from 16328 reflections
c = 14.6878 (4) Åθ = 3.4–32.6°
α = 101.376 (3)°µ = 1.01 mm1
β = 93.421 (3)°T = 100 K
γ = 101.996 (3)°Irregular, clear orange red
V = 1840.80 (11) Å30.19 × 0.12 × 0.11 mm
Data collection top
Oxford Diffraction Gemini Ultra
diffractometer
23898 independent reflections
Radiation source: fine-focus sealed tube, fine-focus sealed tube21552 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 16.0122 pixels mm-1θmax = 32.6°, θmin = 3.4°
ϕ and ω scansh = 1515
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2013)
k = 1818
Tmin = 0.884, Tmax = 0.929l = 2221
40995 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0338P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
23898 reflectionsΔρmax = 1.99 e Å3
895 parametersΔρmin = 0.77 e Å3
3 restraintsAbsolute structure: Flack (1983), 11561 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.039 (12)
Crystal data top
(C12H16NO2)[PdCl2(C12H14NO2)]γ = 101.996 (3)°
Mr = 587.80V = 1840.80 (11) Å3
Triclinic, P1Z = 3
a = 10.6095 (5) ÅMo Kα radiation
b = 12.3870 (4) ŵ = 1.01 mm1
c = 14.6878 (4) ÅT = 100 K
α = 101.376 (3)°0.19 × 0.12 × 0.11 mm
β = 93.421 (3)°
Data collection top
Oxford Diffraction Gemini Ultra
diffractometer
23898 independent reflections
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2013)
21552 reflections with I > 2σ(I)
Tmin = 0.884, Tmax = 0.929Rint = 0.033
40995 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.082Δρmax = 1.99 e Å3
S = 1.03Δρmin = 0.77 e Å3
23898 reflectionsAbsolute structure: Flack (1983), 11561 Friedel pairs
895 parametersAbsolute structure parameter: 0.039 (12)
3 restraints
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
Pd10.67261 (2)0.638283 (17)0.088258 (15)0.01431 (5)
Pd20.46952 (2)0.423409 (17)0.410899 (15)0.01132 (5)
Pd30.08081 (2)0.400908 (17)0.697611 (16)0.01251 (5)
Cl10.82733 (9)0.59507 (7)0.00703 (6)0.02285 (18)
Cl20.64122 (9)0.46476 (7)0.12617 (6)0.01968 (18)
Cl30.48504 (9)0.59104 (7)0.36423 (6)0.01971 (17)
Cl40.45906 (8)0.50373 (6)0.56625 (5)0.01566 (14)
Cl50.16046 (10)0.58439 (7)0.68811 (6)0.02175 (18)
Cl60.04104 (10)0.45607 (7)0.81541 (6)0.02395 (19)
O10.6849 (3)0.7922 (2)0.05762 (17)0.0192 (5)
O20.6409 (3)0.9599 (2)0.11048 (18)0.0211 (5)
O30.6453 (2)0.1864 (2)0.03745 (17)0.0228 (5)
O40.7477 (3)0.0493 (2)0.01369 (17)0.0200 (5)
H40.70520.01640.02340.030*
O50.4467 (2)0.26793 (19)0.43794 (16)0.0160 (5)
O60.4588 (3)0.09164 (19)0.37613 (17)0.0221 (5)
O70.3816 (3)0.84199 (19)0.40754 (16)0.0208 (5)
O80.3906 (3)1.00261 (19)0.51286 (16)0.0180 (5)
H8A0.40521.03330.46730.027*
O90.0186 (2)0.23703 (18)0.70130 (16)0.0159 (5)
O100.0735 (2)0.07173 (18)0.66413 (15)0.0145 (4)
O110.9879 (2)0.81848 (19)0.69815 (16)0.0200 (5)
O120.9414 (2)0.97655 (19)0.77902 (17)0.0190 (5)
H12A0.98671.00800.74250.028*
N10.5421 (3)0.6887 (2)0.17129 (18)0.0144 (5)
H10.55330.66580.22730.017*
C130.6473 (3)0.3179 (3)0.1260 (2)0.0199 (6)
H13A0.66460.37640.16370.024*
H13B0.57020.32630.09280.024*
N30.4768 (3)0.3397 (2)0.27965 (18)0.0123 (5)
H30.54120.38240.25290.015*
N40.3312 (3)0.7084 (2)0.52338 (18)0.0142 (5)
H4A0.38680.69740.47850.017*
H4B0.34640.66870.56810.017*
N50.1816 (3)0.3382 (2)0.59457 (18)0.0126 (5)
H50.26460.38410.60350.015*
N60.8830 (3)0.6868 (2)0.80445 (19)0.0176 (6)
H6C0.95160.67910.77020.021*
H6D0.89040.65420.85500.021*
C10.4041 (3)0.6449 (3)0.1320 (2)0.0176 (6)
H1A0.37090.56790.14240.021*
H1B0.39400.64280.06420.021*
C20.3338 (3)0.7281 (3)0.1850 (2)0.0190 (6)
H2A0.31730.71230.24720.023*
H2B0.25040.72570.14980.023*
C30.4282 (3)0.8428 (3)0.1939 (2)0.0168 (6)
H3A0.42170.89490.25310.020*
H3B0.40920.87780.14110.020*
C40.5650 (3)0.8169 (3)0.1925 (2)0.0141 (6)
C50.6351 (3)0.8593 (3)0.1147 (2)0.0156 (6)
C60.6505 (3)0.8689 (3)0.2858 (2)0.0157 (6)
H6A0.64850.94980.30390.019*
H6B0.61260.83130.33460.019*
C70.7903 (3)0.8593 (3)0.2838 (2)0.0213 (7)
C80.8837 (4)0.9489 (3)0.2675 (3)0.0319 (9)
H80.85961.01620.25890.038*
C91.0122 (4)0.9401 (4)0.2639 (4)0.0444 (12)
H91.07561.00140.25300.053*
C101.0474 (4)0.8421 (5)0.2761 (3)0.0472 (13)
H101.13520.83650.27440.057*
C110.9558 (4)0.7531 (4)0.2908 (3)0.0377 (10)
H110.98010.68540.29810.045*
C120.8278 (4)0.7614 (3)0.2949 (3)0.0270 (8)
H120.76520.69940.30550.032*
N20.7643 (3)0.3282 (2)0.05704 (19)0.0152 (5)
H2C0.83210.38310.06650.018*
H2D0.74410.34820.00310.018*
C140.8023 (3)0.2156 (3)0.0716 (2)0.0143 (6)
C150.7538 (3)0.1640 (3)0.1752 (2)0.0182 (6)
H15A0.81600.19440.21650.022*
H15B0.74010.08060.18850.022*
C160.6262 (4)0.1998 (3)0.1879 (2)0.0229 (7)
H16A0.55480.14690.16830.027*
H16B0.60480.20150.25410.027*
C170.7219 (3)0.1483 (3)0.0092 (2)0.0145 (6)
C180.9478 (3)0.2305 (3)0.0477 (2)0.0165 (6)
H18A0.96920.15530.05770.020*
H18B0.99500.27310.09040.020*
C190.9928 (3)0.2926 (3)0.0522 (2)0.0190 (6)
C200.9786 (4)0.2360 (3)0.1259 (3)0.0267 (8)
H200.94810.15620.11280.032*
C211.0084 (4)0.2950 (4)0.2175 (3)0.0353 (10)
H210.99740.25580.26690.042*
C221.0544 (4)0.4109 (4)0.2374 (3)0.0378 (10)
H221.07380.45130.30050.045*
C231.0720 (4)0.4681 (3)0.1661 (3)0.0334 (9)
H231.10580.54750.18000.040*
C241.0403 (4)0.4094 (3)0.0732 (3)0.0244 (7)
H241.05110.44930.02410.029*
C250.3532 (3)0.3140 (3)0.2181 (2)0.0194 (7)
H25A0.34280.37990.19210.023*
H25B0.27790.29140.25240.023*
C260.3674 (4)0.2162 (3)0.1413 (2)0.0256 (7)
H26A0.28180.17330.10900.031*
H26B0.42250.24370.09480.031*
C270.4316 (3)0.1438 (3)0.1933 (2)0.0165 (6)
H27A0.48960.10670.15390.020*
H27B0.36550.08480.21130.020*
C280.5096 (3)0.2261 (2)0.2806 (2)0.0133 (6)
C290.4682 (3)0.1925 (3)0.3713 (2)0.0146 (6)
C300.6562 (3)0.2364 (3)0.2815 (2)0.0159 (6)
H30A0.67500.16120.28060.019*
H30B0.68450.25990.22400.019*
C310.7341 (3)0.3200 (3)0.3654 (2)0.0170 (6)
C320.7869 (3)0.4312 (3)0.3596 (3)0.0218 (7)
H320.78000.45260.30120.026*
C330.8489 (3)0.5100 (3)0.4371 (3)0.0303 (9)
H330.88530.58500.43160.036*
C340.8586 (4)0.4813 (4)0.5227 (3)0.0336 (9)
H340.89890.53680.57640.040*
C350.8090 (4)0.3709 (4)0.5301 (3)0.0390 (11)
H350.81720.35030.58880.047*
C360.7469 (3)0.2896 (3)0.4511 (3)0.0263 (8)
H360.71370.21390.45610.032*
C370.1922 (3)0.6682 (3)0.4799 (2)0.0183 (6)
H37A0.15200.59510.49500.022*
H37B0.18760.65870.41120.022*
C380.1243 (3)0.7601 (3)0.5223 (2)0.0208 (7)
H38A0.04390.72700.54710.025*
H38B0.10170.80160.47480.025*
C390.2203 (3)0.8389 (3)0.6007 (2)0.0148 (6)
H39A0.21140.81290.66010.018*
H39B0.20720.91700.61010.018*
C400.3523 (3)0.8328 (3)0.5672 (2)0.0120 (6)
C410.3775 (3)0.8929 (3)0.4858 (2)0.0140 (6)
C420.4657 (3)0.8723 (3)0.6432 (2)0.0169 (6)
H42A0.45890.94540.68220.020*
H42B0.45960.81680.68380.020*
C430.5970 (3)0.8866 (3)0.6057 (2)0.0165 (6)
C440.6633 (3)0.9930 (3)0.5974 (2)0.0208 (7)
H440.62861.05720.61850.025*
C450.7794 (4)1.0057 (3)0.5586 (3)0.0258 (8)
H450.82471.07890.55410.031*
C460.8306 (3)0.9130 (3)0.5260 (2)0.0249 (7)
H460.90980.92190.49830.030*
C470.7649 (4)0.8073 (3)0.5345 (3)0.0232 (7)
H470.79960.74330.51280.028*
C480.6497 (3)0.7938 (3)0.5740 (2)0.0191 (6)
H480.60590.72070.57960.023*
C490.1263 (3)0.3306 (3)0.4962 (2)0.0160 (6)
H49A0.19400.36300.45950.019*
H49B0.05540.37140.49570.019*
C500.0754 (3)0.2050 (3)0.4566 (2)0.0188 (6)
H50A0.01350.17900.47280.023*
H50B0.07510.18690.38780.023*
C510.1708 (3)0.1518 (2)0.5033 (2)0.0142 (6)
H51A0.25250.15870.47350.017*
H51B0.13360.07100.50110.017*
C520.1932 (3)0.2208 (2)0.6037 (2)0.0117 (6)
C530.0868 (3)0.1721 (3)0.6605 (2)0.0114 (5)
C540.3267 (3)0.2258 (2)0.6549 (2)0.0125 (5)
H54A0.33890.14800.65080.015*
H54B0.39580.26620.62350.015*
C550.3391 (3)0.2852 (3)0.7567 (2)0.0133 (5)
C560.3866 (3)0.4017 (3)0.7852 (2)0.0160 (6)
H560.41860.44440.74110.019*
C570.3874 (3)0.4556 (3)0.8775 (2)0.0199 (7)
H570.42070.53480.89630.024*
C580.3399 (3)0.3946 (3)0.9425 (2)0.0214 (7)
H580.33900.43201.00540.026*
C590.2937 (4)0.2784 (3)0.9148 (2)0.0219 (7)
H590.26120.23610.95910.026*
C600.2946 (3)0.2240 (3)0.8233 (2)0.0173 (6)
H600.26480.14430.80550.021*
C610.7578 (4)0.6322 (3)0.7458 (3)0.0221 (7)
H61A0.73710.54940.74080.027*
H61B0.75990.64800.68240.027*
C620.6624 (3)0.6863 (3)0.7985 (2)0.0225 (7)
H62A0.63630.64900.85030.027*
H62B0.58400.68230.75670.027*
C630.7358 (3)0.8099 (3)0.8362 (2)0.0188 (6)
H63A0.71490.83770.90020.023*
H63B0.71140.85890.79560.023*
C640.8815 (3)0.8110 (2)0.8366 (2)0.0144 (6)
C650.9438 (3)0.8686 (3)0.7632 (2)0.0142 (6)
C660.9599 (3)0.8611 (3)0.9333 (2)0.0178 (6)
H66A0.94710.93850.95590.021*
H66B0.92500.81490.97780.021*
C671.1026 (3)0.8664 (3)0.9335 (2)0.0188 (6)
C681.1891 (4)0.9682 (3)0.9352 (3)0.0260 (8)
H681.15681.03460.93720.031*
C691.3211 (4)0.9754 (4)0.9340 (3)0.0337 (9)
H691.37841.04630.93700.040*
C701.3692 (4)0.8781 (4)0.9283 (3)0.0366 (10)
H701.45930.88180.92590.044*
C711.2853 (4)0.7771 (4)0.9264 (3)0.0388 (10)
H711.31760.71050.92230.047*
C721.1531 (4)0.7712 (3)0.9302 (3)0.0313 (9)
H721.09670.70080.93070.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.02410 (13)0.00915 (10)0.01240 (10)0.00584 (9)0.00917 (9)0.00436 (8)
Pd20.01530 (11)0.00823 (10)0.01248 (10)0.00385 (8)0.00656 (8)0.00431 (8)
Pd30.01676 (11)0.00978 (10)0.01312 (10)0.00479 (9)0.00536 (9)0.00444 (8)
Cl10.0365 (5)0.0141 (3)0.0248 (4)0.0114 (3)0.0196 (4)0.0096 (3)
Cl20.0323 (5)0.0113 (3)0.0202 (4)0.0082 (3)0.0137 (3)0.0080 (3)
Cl30.0349 (5)0.0120 (3)0.0172 (4)0.0100 (3)0.0126 (3)0.0069 (3)
Cl40.0228 (4)0.0113 (3)0.0139 (3)0.0033 (3)0.0073 (3)0.0040 (3)
Cl50.0346 (5)0.0123 (4)0.0204 (4)0.0062 (3)0.0077 (4)0.0061 (3)
Cl60.0367 (5)0.0166 (4)0.0263 (4)0.0144 (4)0.0198 (4)0.0091 (3)
O10.0339 (15)0.0129 (11)0.0158 (12)0.0102 (11)0.0138 (11)0.0067 (9)
O20.0343 (15)0.0108 (11)0.0236 (12)0.0072 (10)0.0168 (11)0.0097 (9)
O30.0295 (14)0.0172 (11)0.0276 (13)0.0092 (10)0.0159 (11)0.0106 (10)
O40.0299 (14)0.0134 (11)0.0224 (13)0.0074 (10)0.0151 (11)0.0109 (10)
O50.0235 (13)0.0108 (11)0.0161 (11)0.0042 (9)0.0080 (10)0.0067 (9)
O60.0391 (15)0.0099 (10)0.0225 (12)0.0090 (10)0.0149 (11)0.0084 (9)
O70.0358 (14)0.0141 (11)0.0138 (10)0.0052 (10)0.0088 (10)0.0045 (9)
O80.0266 (13)0.0126 (11)0.0162 (11)0.0055 (10)0.0063 (10)0.0040 (9)
O90.0199 (12)0.0109 (10)0.0194 (11)0.0048 (9)0.0107 (9)0.0052 (9)
O100.0179 (11)0.0102 (10)0.0172 (11)0.0035 (8)0.0060 (9)0.0057 (8)
O110.0254 (12)0.0184 (11)0.0201 (11)0.0089 (10)0.0099 (10)0.0066 (9)
O120.0274 (13)0.0122 (10)0.0211 (12)0.0061 (9)0.0122 (10)0.0082 (9)
N10.0242 (14)0.0088 (11)0.0116 (12)0.0039 (10)0.0064 (10)0.0041 (9)
C130.0188 (16)0.0210 (16)0.0224 (16)0.0092 (13)0.0007 (13)0.0056 (13)
N30.0141 (12)0.0083 (11)0.0157 (12)0.0030 (9)0.0060 (10)0.0039 (9)
N40.0186 (13)0.0115 (12)0.0137 (12)0.0042 (10)0.0055 (10)0.0035 (10)
N50.0157 (13)0.0086 (11)0.0135 (12)0.0011 (9)0.0022 (10)0.0040 (9)
N60.0271 (15)0.0085 (12)0.0177 (13)0.0031 (11)0.0027 (11)0.0048 (10)
C10.0216 (16)0.0145 (14)0.0148 (14)0.0023 (12)0.0043 (12)0.0004 (11)
C20.0225 (17)0.0152 (14)0.0190 (15)0.0036 (13)0.0043 (13)0.0033 (12)
C30.0242 (17)0.0107 (13)0.0178 (15)0.0056 (12)0.0085 (13)0.0047 (11)
C40.0245 (17)0.0083 (13)0.0118 (14)0.0071 (12)0.0084 (12)0.0018 (11)
C50.0236 (17)0.0104 (13)0.0142 (14)0.0040 (12)0.0063 (12)0.0047 (11)
C60.0230 (16)0.0104 (13)0.0134 (14)0.0047 (12)0.0052 (12)0.0001 (11)
C70.0242 (17)0.0207 (16)0.0172 (15)0.0074 (14)0.0047 (13)0.0032 (13)
C80.028 (2)0.0283 (19)0.036 (2)0.0050 (16)0.0089 (17)0.0009 (17)
C90.026 (2)0.045 (3)0.053 (3)0.0011 (19)0.011 (2)0.004 (2)
C100.027 (2)0.069 (3)0.042 (3)0.023 (2)0.0043 (19)0.010 (2)
C110.040 (2)0.046 (3)0.030 (2)0.026 (2)0.0016 (18)0.0003 (19)
C120.030 (2)0.031 (2)0.0209 (17)0.0148 (17)0.0001 (15)0.0001 (15)
N20.0172 (13)0.0109 (12)0.0183 (13)0.0040 (10)0.0028 (10)0.0036 (10)
C140.0170 (15)0.0097 (13)0.0186 (15)0.0047 (12)0.0052 (12)0.0060 (12)
C150.0215 (16)0.0188 (15)0.0168 (15)0.0076 (13)0.0051 (12)0.0056 (12)
C160.0272 (18)0.0222 (17)0.0202 (16)0.0100 (14)0.0006 (14)0.0027 (13)
C170.0153 (15)0.0113 (13)0.0175 (15)0.0019 (11)0.0029 (12)0.0052 (11)
C180.0149 (15)0.0183 (15)0.0200 (15)0.0071 (12)0.0063 (12)0.0080 (12)
C190.0135 (14)0.0192 (15)0.0261 (17)0.0062 (12)0.0034 (12)0.0064 (13)
C200.0235 (18)0.0311 (19)0.0286 (19)0.0063 (15)0.0007 (14)0.0141 (16)
C210.025 (2)0.059 (3)0.0248 (19)0.0110 (19)0.0013 (15)0.0135 (19)
C220.0225 (19)0.056 (3)0.027 (2)0.0095 (19)0.0019 (16)0.0070 (19)
C230.0233 (19)0.029 (2)0.041 (2)0.0032 (16)0.0020 (17)0.0073 (17)
C240.0211 (17)0.0225 (17)0.0286 (18)0.0035 (14)0.0057 (14)0.0036 (14)
C250.0194 (16)0.0199 (16)0.0201 (16)0.0083 (13)0.0003 (13)0.0034 (13)
C260.032 (2)0.0216 (17)0.0214 (17)0.0046 (15)0.0006 (15)0.0041 (14)
C270.0216 (16)0.0116 (13)0.0155 (14)0.0024 (12)0.0052 (12)0.0015 (11)
C280.0188 (15)0.0105 (13)0.0138 (14)0.0057 (11)0.0061 (11)0.0061 (11)
C290.0179 (15)0.0111 (13)0.0164 (14)0.0029 (11)0.0070 (12)0.0057 (11)
C300.0173 (15)0.0159 (14)0.0161 (14)0.0057 (12)0.0061 (12)0.0042 (12)
C310.0140 (14)0.0194 (15)0.0199 (15)0.0068 (12)0.0023 (12)0.0062 (12)
C320.0182 (16)0.0209 (16)0.0276 (18)0.0080 (13)0.0014 (14)0.0047 (14)
C330.0167 (17)0.0242 (18)0.046 (2)0.0075 (14)0.0025 (16)0.0038 (17)
C340.0182 (18)0.046 (2)0.029 (2)0.0097 (17)0.0021 (15)0.0099 (18)
C350.024 (2)0.073 (3)0.0230 (19)0.015 (2)0.0010 (16)0.013 (2)
C360.0198 (17)0.036 (2)0.0260 (18)0.0099 (15)0.0007 (14)0.0106 (16)
C370.0206 (16)0.0152 (15)0.0175 (15)0.0008 (12)0.0028 (13)0.0025 (12)
C380.0212 (16)0.0212 (16)0.0200 (15)0.0061 (13)0.0041 (13)0.0022 (13)
C390.0192 (15)0.0134 (14)0.0133 (14)0.0039 (12)0.0068 (12)0.0042 (11)
C400.0164 (14)0.0097 (13)0.0107 (13)0.0029 (11)0.0042 (11)0.0035 (11)
C410.0165 (15)0.0122 (14)0.0153 (14)0.0045 (11)0.0058 (12)0.0050 (11)
C420.0185 (15)0.0175 (15)0.0161 (14)0.0037 (12)0.0027 (12)0.0072 (12)
C430.0163 (15)0.0190 (15)0.0141 (14)0.0026 (12)0.0010 (11)0.0051 (12)
C440.0193 (16)0.0160 (15)0.0233 (16)0.0011 (12)0.0021 (13)0.0004 (13)
C450.0197 (18)0.0252 (18)0.0307 (19)0.0026 (15)0.0010 (15)0.0108 (15)
C460.0160 (16)0.0330 (19)0.0230 (17)0.0012 (14)0.0018 (13)0.0045 (15)
C470.0194 (17)0.0223 (17)0.0255 (17)0.0072 (14)0.0012 (14)0.0023 (14)
C480.0206 (16)0.0174 (15)0.0190 (15)0.0052 (13)0.0016 (12)0.0036 (12)
C490.0192 (15)0.0170 (14)0.0147 (14)0.0043 (12)0.0046 (12)0.0096 (12)
C500.0250 (17)0.0184 (15)0.0140 (14)0.0053 (13)0.0019 (12)0.0053 (12)
C510.0181 (15)0.0094 (13)0.0156 (14)0.0027 (11)0.0051 (11)0.0034 (11)
C520.0130 (14)0.0084 (13)0.0145 (14)0.0014 (11)0.0041 (11)0.0049 (11)
C530.0119 (13)0.0120 (13)0.0099 (12)0.0002 (10)0.0029 (10)0.0034 (10)
C540.0138 (14)0.0112 (13)0.0137 (13)0.0041 (11)0.0037 (11)0.0037 (11)
C550.0118 (13)0.0146 (14)0.0148 (13)0.0038 (11)0.0031 (11)0.0047 (11)
C560.0207 (16)0.0112 (13)0.0163 (14)0.0032 (12)0.0002 (12)0.0043 (11)
C570.0247 (17)0.0134 (14)0.0202 (16)0.0042 (13)0.0003 (13)0.0007 (12)
C580.0230 (17)0.0252 (17)0.0150 (15)0.0056 (14)0.0041 (13)0.0012 (13)
C590.0252 (18)0.0240 (17)0.0153 (15)0.0008 (14)0.0022 (13)0.0063 (13)
C600.0182 (15)0.0157 (14)0.0169 (14)0.0005 (12)0.0001 (12)0.0051 (12)
C610.0255 (18)0.0116 (14)0.0252 (17)0.0000 (13)0.0023 (14)0.0002 (13)
C620.0219 (17)0.0197 (16)0.0235 (17)0.0014 (13)0.0010 (13)0.0066 (13)
C630.0182 (16)0.0188 (15)0.0197 (15)0.0021 (12)0.0078 (13)0.0051 (12)
C640.0191 (15)0.0070 (12)0.0182 (14)0.0019 (11)0.0063 (12)0.0049 (11)
C650.0164 (14)0.0123 (13)0.0159 (14)0.0036 (11)0.0053 (11)0.0061 (11)
C660.0250 (17)0.0116 (14)0.0160 (15)0.0005 (12)0.0059 (13)0.0035 (12)
C670.0270 (17)0.0171 (15)0.0105 (13)0.0034 (13)0.0003 (12)0.0009 (12)
C680.0248 (18)0.0210 (17)0.0323 (19)0.0018 (14)0.0029 (15)0.0092 (15)
C690.027 (2)0.034 (2)0.039 (2)0.0004 (17)0.0017 (17)0.0132 (18)
C700.025 (2)0.051 (3)0.034 (2)0.0130 (19)0.0058 (17)0.007 (2)
C710.041 (2)0.034 (2)0.041 (2)0.0191 (19)0.0160 (19)0.0010 (19)
C720.036 (2)0.0191 (17)0.036 (2)0.0041 (16)0.0114 (17)0.0058 (16)
Geometric parameters (Å, º) top
Pd1—Cl12.2986 (8)C25—H25B0.9900
Pd1—Cl22.2886 (8)C25—C261.523 (5)
Pd1—O12.024 (2)C26—H26A0.9900
Pd1—N12.014 (3)C26—H26B0.9900
Pd2—Cl32.2894 (8)C26—C271.521 (5)
Pd2—Cl42.3215 (7)C27—H27A0.9900
Pd2—O52.011 (2)C27—H27B0.9900
Pd2—N32.015 (3)C27—C281.542 (4)
Pd3—Cl52.2891 (9)C28—C291.534 (4)
Pd3—Cl62.3021 (9)C28—C301.533 (4)
Pd3—O92.012 (2)C30—H30A0.9900
Pd3—N52.028 (3)C30—H30B0.9900
O1—C51.278 (4)C30—C311.514 (4)
O2—C51.249 (4)C31—C321.396 (5)
O3—C171.204 (4)C31—C361.391 (5)
O4—H40.8400C32—H320.9500
O4—C171.301 (4)C32—C331.374 (5)
O5—C291.279 (4)C33—H330.9500
O6—C291.249 (4)C33—C341.376 (6)
O7—C411.205 (4)C34—H340.9500
O8—H8A0.8400C34—C351.388 (7)
O8—C411.313 (4)C35—H350.9500
O9—C531.278 (4)C35—C361.402 (6)
O10—C531.234 (4)C36—H360.9500
O11—C651.207 (4)C37—H37A0.9900
O12—H12A0.8400C37—H37B0.9900
O12—C651.317 (4)C37—C381.523 (5)
N1—H10.9300C38—H38A0.9900
N1—C11.488 (4)C38—H38B0.9900
N1—C41.521 (4)C38—C391.524 (5)
C13—H13A0.9900C39—H39A0.9900
C13—H13B0.9900C39—H39B0.9900
C13—N21.522 (4)C39—C401.524 (4)
C13—C161.527 (5)C40—C411.537 (4)
N3—H30.9300C40—C421.521 (4)
N3—C251.487 (4)C42—H42A0.9900
N3—C281.521 (4)C42—H42B0.9900
N4—H4A0.9200C42—C431.517 (4)
N4—H4B0.9200C43—C441.391 (5)
N4—C371.512 (4)C43—C481.393 (5)
N4—C401.512 (4)C44—H440.9500
N5—H50.9300C44—C451.380 (5)
N5—C491.505 (4)C45—H450.9500
N5—C521.516 (4)C45—C461.384 (5)
N6—H6C0.9200C46—H460.9500
N6—H6D0.9200C46—C471.382 (5)
N6—C611.491 (5)C47—H470.9500
N6—C641.521 (4)C47—C481.377 (5)
C1—H1A0.9900C48—H480.9500
C1—H1B0.9900C49—H49A0.9900
C1—C21.515 (4)C49—H49B0.9900
C2—H2A0.9900C49—C501.519 (4)
C2—H2B0.9900C50—H50A0.9900
C2—C31.535 (4)C50—H50B0.9900
C3—H3A0.9900C50—C511.518 (4)
C3—H3B0.9900C51—H51A0.9900
C3—C41.551 (5)C51—H51B0.9900
C4—C51.520 (4)C51—C521.528 (4)
C4—C61.541 (5)C52—C531.537 (4)
C6—H6A0.9900C52—C541.547 (4)
C6—H6B0.9900C54—H54A0.9900
C6—C71.514 (5)C54—H54B0.9900
C7—C81.395 (5)C54—C551.515 (4)
C7—C121.389 (5)C55—C561.395 (4)
C8—H80.9500C55—C601.397 (4)
C8—C91.393 (6)C56—H560.9500
C9—H90.9500C56—C571.386 (4)
C9—C101.382 (7)C57—H570.9500
C10—H100.9500C57—C581.385 (5)
C10—C111.371 (7)C58—H580.9500
C11—H110.9500C58—C591.389 (5)
C11—C121.387 (6)C59—H590.9500
C12—H120.9500C59—C601.381 (4)
N2—H2C0.9200C60—H600.9500
N2—H2D0.9200C61—H61A0.9900
N2—C141.510 (4)C61—H61B0.9900
C14—C151.541 (5)C61—C621.498 (5)
C14—C171.537 (4)C62—H62A0.9900
C14—C181.527 (5)C62—H62B0.9900
C15—H15A0.9900C62—C631.541 (5)
C15—H15B0.9900C63—H63A0.9900
C15—C161.522 (5)C63—H63B0.9900
C16—H16A0.9900C63—C641.543 (5)
C16—H16B0.9900C64—C651.516 (4)
C18—H18A0.9900C64—C661.546 (5)
C18—H18B0.9900C66—H66A0.9900
C18—C191.513 (5)C66—H66B0.9900
C19—C201.401 (5)C66—C671.502 (5)
C19—C241.394 (5)C67—C681.392 (5)
C20—H200.9500C67—C721.387 (5)
C20—C211.382 (6)C68—H680.9500
C21—H210.9500C68—C691.386 (6)
C21—C221.383 (7)C69—H690.9500
C22—H220.9500C69—C701.393 (6)
C22—C231.377 (6)C70—H700.9500
C23—H230.9500C70—C711.370 (6)
C23—C241.399 (5)C71—H710.9500
C24—H240.9500C71—C721.395 (6)
C25—H25A0.9900C72—H720.9500
Cl2—Pd1—Cl191.05 (3)C29—C28—C27112.1 (2)
O1—Pd1—Cl193.45 (7)C30—C28—C27113.1 (2)
O1—Pd1—Cl2175.09 (8)C30—C28—C29108.1 (3)
N1—Pd1—Cl1175.58 (8)O5—C29—C28119.3 (3)
N1—Pd1—Cl293.22 (8)O6—C29—O5123.4 (3)
N1—Pd1—O182.33 (10)O6—C29—C28117.3 (3)
Cl3—Pd2—Cl493.56 (3)C28—C30—H30A108.9
O5—Pd2—Cl3173.81 (8)C28—C30—H30B108.9
O5—Pd2—Cl491.87 (7)H30A—C30—H30B107.7
O5—Pd2—N382.76 (10)C31—C30—C28113.6 (3)
N3—Pd2—Cl391.81 (7)C31—C30—H30A108.9
N3—Pd2—Cl4174.63 (7)C31—C30—H30B108.9
Cl5—Pd3—Cl691.58 (3)C32—C31—C30120.5 (3)
O9—Pd3—Cl5176.70 (7)C36—C31—C30120.6 (3)
O9—Pd3—Cl691.65 (7)C36—C31—C32118.8 (3)
O9—Pd3—N583.36 (9)C31—C32—H32119.5
N5—Pd3—Cl593.41 (7)C33—C32—C31121.0 (3)
N5—Pd3—Cl6175.01 (8)C33—C32—H32119.5
C5—O1—Pd1114.3 (2)C32—C33—H33119.7
C17—O4—H4109.5C32—C33—C34120.5 (4)
C29—O5—Pd2114.85 (19)C34—C33—H33119.7
C41—O8—H8A109.5C33—C34—H34120.2
C53—O9—Pd3114.33 (19)C33—C34—C35119.7 (4)
C65—O12—H12A109.5C35—C34—H34120.2
Pd1—N1—H1108.3C34—C35—H35119.9
C1—N1—Pd1115.27 (19)C34—C35—C36120.1 (4)
C1—N1—H1108.3C36—C35—H35119.9
C1—N1—C4106.4 (3)C31—C36—C35119.9 (4)
C4—N1—Pd1110.01 (19)C31—C36—H36120.1
C4—N1—H1108.3C35—C36—H36120.1
H13A—C13—H13B108.8N4—C37—H37A110.7
N2—C13—H13A110.7N4—C37—H37B110.7
N2—C13—H13B110.7N4—C37—C38105.2 (3)
N2—C13—C16105.1 (3)H37A—C37—H37B108.8
C16—C13—H13A110.7C38—C37—H37A110.7
C16—C13—H13B110.7C38—C37—H37B110.7
Pd2—N3—H3108.7C37—C38—H38A110.6
C25—N3—Pd2114.5 (2)C37—C38—H38B110.6
C25—N3—H3108.7C37—C38—C39105.8 (3)
C25—N3—C28105.7 (2)H38A—C38—H38B108.7
C28—N3—Pd2110.33 (18)C39—C38—H38A110.6
C28—N3—H3108.7C39—C38—H38B110.6
H4A—N4—H4B108.5C38—C39—H39A111.0
C37—N4—H4A110.2C38—C39—H39B111.0
C37—N4—H4B110.2C38—C39—C40104.0 (3)
C37—N4—C40107.6 (2)H39A—C39—H39B109.0
C40—N4—H4A110.2C40—C39—H39A111.0
C40—N4—H4B110.2C40—C39—H39B111.0
Pd3—N5—H5107.9N4—C40—C39101.3 (2)
C49—N5—Pd3116.2 (2)N4—C40—C41104.8 (2)
C49—N5—H5107.9N4—C40—C42112.3 (3)
C49—N5—C52107.9 (2)C39—C40—C41111.5 (3)
C52—N5—Pd3108.81 (18)C42—C40—C39115.0 (3)
C52—N5—H5107.9C42—C40—C41111.1 (2)
H6C—N6—H6D108.6O7—C41—O8126.3 (3)
C61—N6—H6C110.4O7—C41—C40122.1 (3)
C61—N6—H6D110.4O8—C41—C40111.6 (3)
C61—N6—C64106.5 (3)C40—C42—H42A108.9
C64—N6—H6C110.4C40—C42—H42B108.9
C64—N6—H6D110.4H42A—C42—H42B107.7
N1—C1—H1A110.9C43—C42—C40113.5 (3)
N1—C1—H1B110.9C43—C42—H42A108.9
N1—C1—C2104.3 (2)C43—C42—H42B108.9
H1A—C1—H1B108.9C44—C43—C42120.0 (3)
C2—C1—H1A110.9C44—C43—C48118.7 (3)
C2—C1—H1B110.9C48—C43—C42121.1 (3)
C1—C2—H2A111.1C43—C44—H44119.8
C1—C2—H2B111.1C45—C44—C43120.3 (3)
C1—C2—C3103.4 (3)C45—C44—H44119.8
H2A—C2—H2B109.0C44—C45—H45119.6
C3—C2—H2A111.1C44—C45—C46120.8 (3)
C3—C2—H2B111.1C46—C45—H45119.6
C2—C3—H3A110.6C45—C46—H46120.5
C2—C3—H3B110.6C47—C46—C45119.0 (3)
C2—C3—C4105.5 (3)C47—C46—H46120.5
H3A—C3—H3B108.8C46—C47—H47119.6
C4—C3—H3A110.6C48—C47—C46120.8 (3)
C4—C3—H3B110.6C48—C47—H47119.6
N1—C4—C3105.4 (3)C43—C48—H48119.8
N1—C4—C6110.8 (3)C47—C48—C43120.5 (3)
C5—C4—N1108.0 (2)C47—C48—H48119.8
C5—C4—C3111.3 (3)N5—C49—H49A110.8
C5—C4—C6108.6 (3)N5—C49—H49B110.8
C6—C4—C3112.6 (3)N5—C49—C50104.7 (2)
O1—C5—C4119.5 (3)H49A—C49—H49B108.9
O2—C5—O1123.3 (3)C50—C49—H49A110.8
O2—C5—C4117.2 (3)C50—C49—H49B110.8
C4—C6—H6A108.6C49—C50—H50A111.1
C4—C6—H6B108.6C49—C50—H50B111.1
H6A—C6—H6B107.6H50A—C50—H50B109.1
C7—C6—C4114.5 (3)C51—C50—C49103.2 (3)
C7—C6—H6A108.6C51—C50—H50A111.1
C7—C6—H6B108.6C51—C50—H50B111.1
C8—C7—C6119.9 (3)C50—C51—H51A111.2
C12—C7—C6121.4 (3)C50—C51—H51B111.2
C12—C7—C8118.7 (4)C50—C51—C52102.9 (2)
C7—C8—H8119.9H51A—C51—H51B109.1
C9—C8—C7120.3 (4)C52—C51—H51A111.2
C9—C8—H8119.9C52—C51—H51B111.2
C8—C9—H9120.0N5—C52—C51104.5 (2)
C10—C9—C8119.9 (4)N5—C52—C53109.6 (2)
C10—C9—H9120.0N5—C52—C54110.2 (2)
C9—C10—H10119.9C51—C52—C53109.9 (2)
C11—C10—C9120.1 (4)C51—C52—C54114.1 (3)
C11—C10—H10119.9C53—C52—C54108.5 (2)
C10—C11—H11119.9O9—C53—C52118.8 (3)
C10—C11—C12120.3 (4)O10—C53—O9124.0 (3)
C12—C11—H11119.9O10—C53—C52117.2 (3)
C7—C12—H12119.7C52—C54—H54A109.2
C11—C12—C7120.7 (4)C52—C54—H54B109.2
C11—C12—H12119.7H54A—C54—H54B107.9
C13—N2—H2C110.0C55—C54—C52112.1 (2)
C13—N2—H2D110.0C55—C54—H54A109.2
H2C—N2—H2D108.4C55—C54—H54B109.2
C14—N2—C13108.6 (2)C56—C55—C54121.4 (3)
C14—N2—H2C110.0C56—C55—C60118.6 (3)
C14—N2—H2D110.0C60—C55—C54119.8 (3)
N2—C14—C15102.4 (2)C55—C56—H56119.8
N2—C14—C17105.7 (3)C57—C56—C55120.4 (3)
N2—C14—C18111.3 (3)C57—C56—H56119.8
C17—C14—C15110.0 (3)C56—C57—H57119.8
C18—C14—C15114.4 (3)C58—C57—C56120.5 (3)
C18—C14—C17112.3 (3)C58—C57—H57119.8
C14—C15—H15A111.1C57—C58—H58120.3
C14—C15—H15B111.1C57—C58—C59119.4 (3)
H15A—C15—H15B109.0C59—C58—H58120.3
C16—C15—C14103.5 (3)C58—C59—H59119.8
C16—C15—H15A111.1C60—C59—C58120.4 (3)
C16—C15—H15B111.1C60—C59—H59119.8
C13—C16—H16A110.7C55—C60—H60119.7
C13—C16—H16B110.7C59—C60—C55120.6 (3)
C15—C16—C13105.5 (3)C59—C60—H60119.7
C15—C16—H16A110.7N6—C61—H61A111.2
C15—C16—H16B110.7N6—C61—H61B111.2
H16A—C16—H16B108.8N6—C61—C62102.8 (3)
O3—C17—O4126.1 (3)H61A—C61—H61B109.1
O3—C17—C14121.8 (3)C62—C61—H61A111.2
O4—C17—C14112.1 (3)C62—C61—H61B111.2
C14—C18—H18A109.1C61—C62—H62A110.9
C14—C18—H18B109.1C61—C62—H62B110.9
H18A—C18—H18B107.9C61—C62—C63104.3 (3)
C19—C18—C14112.4 (3)H62A—C62—H62B108.9
C19—C18—H18A109.1C63—C62—H62A110.9
C19—C18—H18B109.1C63—C62—H62B110.9
C20—C19—C18121.0 (3)C62—C63—H63A110.4
C24—C19—C18120.2 (3)C62—C63—H63B110.4
C24—C19—C20118.5 (3)C62—C63—C64106.6 (3)
C19—C20—H20119.7H63A—C63—H63B108.6
C21—C20—C19120.7 (4)C64—C63—H63A110.4
C21—C20—H20119.7C64—C63—H63B110.4
C20—C21—H21119.9N6—C64—C63103.3 (2)
C20—C21—C22120.2 (4)N6—C64—C66110.9 (3)
C22—C21—H21119.9C63—C64—C66113.8 (3)
C21—C22—H22119.9C65—C64—N6105.4 (2)
C23—C22—C21120.2 (4)C65—C64—C63112.5 (3)
C23—C22—H22119.9C65—C64—C66110.4 (3)
C22—C23—H23120.0O11—C65—O12125.6 (3)
C22—C23—C24120.0 (4)O11—C65—C64122.4 (3)
C24—C23—H23120.0O12—C65—C64112.0 (3)
C19—C24—C23120.3 (4)C64—C66—H66A108.7
C19—C24—H24119.8C64—C66—H66B108.7
C23—C24—H24119.8H66A—C66—H66B107.6
N3—C25—H25A111.1C67—C66—C64114.1 (3)
N3—C25—H25B111.1C67—C66—H66A108.7
N3—C25—C26103.3 (3)C67—C66—H66B108.7
H25A—C25—H25B109.1C68—C67—C66120.4 (3)
C26—C25—H25A111.1C72—C67—C66122.0 (3)
C26—C25—H25B111.1C72—C67—C68117.6 (4)
C25—C26—H26A111.0C67—C68—H68119.1
C25—C26—H26B111.0C69—C68—C67121.8 (4)
H26A—C26—H26B109.0C69—C68—H68119.1
C27—C26—C25103.7 (3)C68—C69—H69120.2
C27—C26—H26A111.0C68—C69—C70119.7 (4)
C27—C26—H26B111.0C70—C69—H69120.2
C26—C27—H27A110.7C69—C70—H70120.4
C26—C27—H27B110.7C71—C70—C69119.3 (4)
C26—C27—C28105.4 (3)C71—C70—H70120.4
H27A—C27—H27B108.8C70—C71—H71119.7
C28—C27—H27A110.7C70—C71—C72120.7 (4)
C28—C27—H27B110.7C72—C71—H71119.7
N3—C28—C27105.7 (2)C67—C72—C71121.0 (4)
N3—C28—C29107.4 (2)C67—C72—H72119.5
N3—C28—C30110.3 (2)C71—C72—H72119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.841.692.521 (3)171
O8—H8A···O6ii0.841.712.547 (3)171
O12—H12A···O10iii0.841.732.565 (3)177
N1—H1···Cl30.932.463.334 (3)156
N2—H2C···Cl6iv0.922.453.249 (3)145
N3—H3···Cl20.932.483.354 (3)156
N4—H4A···Cl30.922.353.216 (3)156
N5—H5···Cl40.932.443.319 (3)159
N6—H6D···Cl1v0.922.373.235 (3)156
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z1; (v) x, y, z+1.

Experimental details

Crystal data
Chemical formula(C12H16NO2)[PdCl2(C12H14NO2)]
Mr587.80
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.6095 (5), 12.3870 (4), 14.6878 (4)
α, β, γ (°)101.376 (3), 93.421 (3), 101.996 (3)
V3)1840.80 (11)
Z3
Radiation typeMo Kα
µ (mm1)1.01
Crystal size (mm)0.19 × 0.12 × 0.11
Data collection
DiffractometerOxford Diffraction Gemini Ultra
diffractometer
Absorption correctionGaussian
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.884, 0.929
No. of measured, independent and
observed [I > 2σ(I)] reflections
40995, 23898, 21552
Rint0.033
(sin θ/λ)max1)0.757
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.082, 1.03
No. of reflections23898
No. of parameters895
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.99, 0.77
Absolute structureFlack (1983), 11561 Friedel pairs
Absolute structure parameter0.039 (12)

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.841.692.521 (3)170.8
O8—H8A···O6ii0.841.712.547 (3)171.1
O12—H12A···O10iii0.841.732.565 (3)177.4
N1—H1···Cl30.932.463.334 (3)156.2
N2—H2C···Cl6iv0.922.453.249 (3)144.7
N3—H3···Cl20.932.483.354 (3)156.0
N4—H4A···Cl30.922.353.216 (3)155.8
N5—H5···Cl40.932.443.319 (3)158.5
N6—H6D···Cl1v0.922.373.235 (3)155.9
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z1; (v) x, y, z+1.
 

Acknowledgements

The authors would like to thank the Virginia Tech Department of Chemistry and the Virginia Tech Crystallography Laboratory for their support.

References

First citationAgilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
First citationAkat'eva, M. E., Erofeeva, O. S., Dobrynina, N. A., Ivanova, N. A. & Efimenko, I. A. (2004). Russ. J. Coord. Chem. 30, 584–590.  CAS
First citationAsanin, D. P., Rajkovic, S., Molnar-Gabor, D. & Djuran, M. I. (2004). Monatsh. Chem. 135, 1445–1453.  CAS
First citationChernova, N. N., Kurskii, I. G., Vashchenko, L. P. & Ivanchenko, O. N. (1978). Zh. Neorg. Khim. 23, 1314–1318.  CAS
First citationChernova, N. N., Shakhova, L. P. & Kukushkin, Y. N. (1976). Zh. Neorg. Khim. 21, 3027–3030.  CAS
First citationCordova, A., Sunden, H., Engqvist, M., Ibrahem, I. & Casas, J. (2004). J. Am. Chem. Soc. 126, 8914–8915.  Web of Science PubMed CAS
First citationDjuran, M. I. & Milinkovic, S. U. (1999). Polyhedron, 18, 3611–3616.  Web of Science CrossRef CAS
First citationDjuran, M. I. & Milinkovic, S. U. (2000). Polyhedron, 19, 959–963.  Web of Science CrossRef CAS
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals
First citationFaraglia, G., Fregona, D. & Sitran, S. (1997). Transition Met. Chem. 22, 492–496.  CrossRef CAS Web of Science
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationHao, Y.-Z., Li, Z.-X. & Tian, J.-L. (2007). J. Mol. Catal. A Chem. 265, 258–267.  Web of Science CSD CrossRef CAS
First citationHao, Y.-Z., Zhang, Y.-L., Wang, L.-H. & Ju, X.-Y. (2009). Open Catal. J. 2, 66–70.  CrossRef CAS
First citationKrylova, L. F., Dikanskaya, L. D. & Fedotov, M. A. (1994). Koord. Khim. 20, 57–59.  CAS
First citationRispens, M. T., Zondervan, C. & Feringa, B. L. (1995). Tetrahedron Asymmetry, 6, 661–664.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpacu, P. & Ungureanu-Vicol, O. (1966). An. Univ. Bucuresti Ser. Stiint. Natur. 15, 109–118.  CAS
First citationSutar, R. L. & Joshi, N. N. (2013). Tetrahedron Asymmetry, 24, 43–49.  Web of Science CrossRef CAS
First citationVicol, O. & Harabor, P. (1974). An. Stiint. Univ. Al. I. Cuza Iasi Sect. 1c, 20, 117–123.  CAS

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Volume 69| Part 5| May 2013| Pages m261-m262
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