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In the title compounds, [Pd(C10H6O2)(C10H8N2)], (I), and [Pd(C10H6O2)(C18H12N2)], (II), each PdII atom has a similar distorted cis-planar four-coordination geometry involving two O atoms of the 2,3-­naphthalenediolate dianion and two N atoms of the 2,2′-bi­pyridine or 2,2′-bi­quinoline ligand. The overall structure of (I) is essentially planar, but that of (II) is not, as a result of intramolecular overcrowding leading to bowing of the bi­quinoline ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104002690/fg1730sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104002690/fg1730Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104002690/fg1730IIsup3.hkl
Contains datablock II

CCDC references: 237906; 237907

Comment top

Recently, the palladium complex [Pd(bpy)(cbdca)] (where bpy is 2,2'-bipyridine and cbdca is the 1,1-cyclobutanedicarboxylate ligand), with a cis-square-planar coordination geometry, has been shown to have better cytotoxic activity than cisplatin, cis-diamminedichloroplatinum(II), against P388 lymphocytic leukemia cells (Mansuri-Torshizi et al., 2001).

The planar aromatic ligands interact with DNA, which is the principal target in the chemotherapy of tumors (Neidle et al., 1987; Cusumano & Giannetto, 1997; Shehata, 2001). In the present study, we have prepared two cis-coordinated ternary complexes of PdII, with the aromatic ligands bpy, 2,2'-biquinoline (biq) and 2,3-naphthalenediol (nad), namely the title complexes [Pd(bpy)(nad)], (I), and [Pd(biq)(nad)], (II), and determined their structures. The same complexes have previously been synthesized by a different method for electrochemical studies into their use as photosensitizers in inorganic photochemistry (Kamath et al., 1989). Structures have been determined for complexes of nad with Si (Holmes et al., 1985; Strohmann et al., 1991; Tacke et al., 1991; Sperlich et al., 1993; Tacke et al., 1993), Fe (Jü stel et al., 1999), Ge (Tacke et al., 1994), Rb (Yang et al., 1997), Mo (El-Hendawy et al., 1989; Mondal et al., 1988; Kang et al., 1989) and Sb (Holmes et al., 1987). The present study is the first determination of the crystal structures of Pd complexes with nad.

The central Pd atom of each complex has the same distorted cis-square-planer coordination geometry, involving the two N atoms of the heterocycle and the two O atoms of the dianion of the nad ligand (Figs. 1 and 2). The overall structure of (I) is essentially planar. Atom C14 of the bpy ligand ?shows the maximum deviation from the mean molecular plane [0.085 (3) Å].

In contrast, the overall structure of (II) is not planar; the dihedral angle between the biq and Pd(nad) planes is 148.73 (7)°. In the square-planar coordination, atoms Pd1, N1, N2, O1 and O2 deviate by 0.0055 (1), −0.135 (3), −0.073 (3), −0.093 (3) and −0.167 (3) Å, respectively, from the plane through these five atoms, while the Pd(nad) moiety, including the square-planar coordination plane, is mostly planar, the maximum deviation from the plane being that of atom C26 [0.139 (7) Å]. The biq molecule is bowed to relieve intramolecular overcrowding between the biq moieties (C9/H9 and C19/H19) and nad atoms (O1 and O2). The H9···O1 and H19···O2 separations are 2.23 and 2.28 Å, respectively. As a result, the angle between the two quinoline ring planes is 19.9 (1) °.

Selected bond lengths and bond angles in (I), (II) are listed in Tables 2 and 3. The Pd—O bond lengths in (I) and (II) are similar, but the Pd—N distances in (I) are slightly shorter than those in (II). These values may be compared with those reported for [Pd(NH3)2(cbdca)] (III; Barnham et al., 1994), [Pd(en)(cbdca)] (IV; en is ethylenediamine; Tercero et al., 2003) and [Pd(cat)(phen)] (V; cat is cathecholate and phen is 1,10-phenanthloline; Okabe et al., 2003), since the central Pd atoms of all of these compounds have the same distorted cis-square-planar coordination geometry, with the formula [Pd(NN)(OO)]. The Pd—N bonds of (I) are slightly shorter than those in (III)–(IV) [2.020 (7)–2.030 (2) Å] and are nearly the same as those in (V) [2.003 (2)–2.019 (2) Å]. The Pd—N distances in (II) are slightly longer than those in (III)–(V). The Pd—O bond lengths in (I) and (II) are also slightly shorter than those in (III)–(IV) [2.005 (2)–2.017 (6) Å] and nearly the same as those in (V) [1.981 (2)–1.989 (2) Å]. It thus appears that the coordination bonds in (I) are stronger than those in (III)–(IV) or nearly identical to those in (V). The Pd—N bonds in (II) are the weakest of all, possibly as a result of intramolecular steric hindrance between the O atoms of the dianion of the nad molecule and the H atoms attached to atoms C9 and C19 of the biq molecule, as noted above.

The O—Pd—O angles in the five-membered rings in (I) and (II) are small compared with those observed in the six-membered rings in (III) and (IV) [90.9–92.69 (7)°], and slightly smaller than that reported for the five-membered ring in (V) [85.09 (7) °]. The N—Pd—N angles in (I) and (II) are also smaller than those in (IV) [84.15 (8) ° for en] and in (III) [95.0° for NH3—Pd—NH3], and slightly smaller than that in (V) [81.69 (8) ° for cat].

The crystal structure of (I) is stabilized by centrosymmetric stacking interactions between molecules at (1 − x,-y,1 − z), (x,y,z), (1 − x,1 − y,1 − z), (x,1 + y,z) etc., as shown in Fig. 3, the shortest separations being between atoms Pd1 and C26 [at (1 − x,1 − y,1 − z); 3.391 (2) Å], and between atoms Pd1 and C12 [at (1 − x,-y,1 − z); 3.414 (2) Å]. The crystal structure of (II) exhibits interactions between inversion-related molecules, as shown in Fig. 4, the shortest separations being between atoms Pd1 and C3 [at (1 − x,-y,1 − z); 3.219 (6) Å], and between atoms Pd1 and C30 [at (2 − x,-y,1 − z); 3.449 (5) Å]. These stacks are then connected by C—H···π arene interactions [H6.·Cg1 = 2.50 Å, C6···Cg1 = 3.431 Å and C6—H6···Cg1 = 176°; Cg1 is the centroid of the C23–C28 ring at (3/2 − x,-1/2 + y,5/2 − z)].

Experimental top

For the preparation of (I), bpy was reacted with palladium acetate (Pd(CH3COOH)2) for 30 min at room temperature (molar ratio 2:3) in dimethylformamide (DMF), and then nad (equivalent to bpy) dissolved to DMF was added. This mixture was left to stand at room temperature, and red prismatic crystals appeared after a few days. Complex (II) was synthesized by a similar method, except that biq was used instead of bpy. Colorless prismatic crystals appeared after a few days.

Refinement top

For (I) and (II), all H atoms were located from difference Fourier maps and then placed at idealized positions and treated as riding, with C—H distances of 0.93 Å and Uiso(H) values equal to 1.2Ueq(C).

Computing details top

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); data reduction: TEXSAN (Molecular Structure Corporation, 2000). Program(s) used to solve structure: SIR97 (Altomare et al., 1999) for (I); SHELXS97 (Scheldrick, 1997) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Scheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN (Molecular Structure Corporation, 2000).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are shown at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of (II), with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are shown at the 50% probability level.
[Figure 3] Fig. 3. A stereoview of the packing in (I), showing the ring interactions.
[Figure 4] Fig. 4. A stereoview of the packing of (II), showing the ring and C—H···π interactions
(I) top
Crystal data top
[Pd(C10H6O2)(C10H8N2)]F(000) = 840.0
Mr = 420.75Dx = 1.754 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.117 (2) Åθ = 14.8–15.0°
b = 8.239 (2) ŵ = 1.18 mm1
c = 16.857 (1) ÅT = 296 K
β = 108.804 (8)°Plate, red
V = 1593.1 (5) Å30.50 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.014
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)
h = 015
Tmin = 0.936, Tmax = 1.000k = 010
4095 measured reflectionsl = 2120
3658 independent reflections3 standard reflections every 150 reflections
3090 reflections with I > 2σ(I) intensity decay: 1.1%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027 w = 1/[σ2(Fo2) + (0.0381P)2 + 0.8904P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max = 0.001
S = 1.14Δρmax = 0.38 e Å3
3658 reflectionsΔρmin = 0.88 e Å3
226 parameters
Crystal data top
[Pd(C10H6O2)(C10H8N2)]V = 1593.1 (5) Å3
Mr = 420.75Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.117 (2) ŵ = 1.18 mm1
b = 8.239 (2) ÅT = 296 K
c = 16.857 (1) Å0.50 × 0.20 × 0.20 mm
β = 108.804 (8)°
Data collection top
Rigaku AFC-5R
diffractometer
3090 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)
Rint = 0.014
Tmin = 0.936, Tmax = 1.0003 standard reflections every 150 reflections
4095 measured reflections intensity decay: 1.1%
3658 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027226 parameters
wR(F2) = 0.078H-atom parameters constrained
S = 1.14Δρmax = 0.38 e Å3
3658 reflectionsΔρmin = 0.88 e Å3
Special details top

Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.49700 (2)0.23263 (2)0.47388 (1)0.03169 (8)
O10.6355 (2)0.3261 (3)0.4527 (1)0.0409 (4)
O20.5596 (2)0.3391 (3)0.5850 (1)0.0391 (4)
N10.4318 (2)0.1172 (3)0.3641 (1)0.0351 (5)
N20.3573 (2)0.1303 (3)0.4920 (1)0.0344 (5)
C20.3331 (2)0.0323 (3)0.3547 (2)0.0353 (5)
C30.2787 (3)0.0528 (4)0.2817 (2)0.0467 (7)
C40.3268 (3)0.0503 (4)0.2181 (2)0.0507 (8)
C50.4275 (3)0.0360 (4)0.2277 (2)0.0479 (7)
C60.4779 (3)0.1182 (4)0.3014 (2)0.0429 (6)
C120.2903 (2)0.0389 (3)0.4273 (2)0.0340 (5)
C130.1932 (3)0.0426 (4)0.4322 (2)0.0433 (6)
C140.1648 (3)0.0308 (4)0.5051 (2)0.0523 (8)
C150.2331 (3)0.0630 (5)0.5700 (2)0.0551 (8)
C160.3275 (3)0.1433 (4)0.5613 (2)0.0450 (7)
C170.6984 (2)0.4126 (3)0.5193 (2)0.0349 (5)
C180.7994 (3)0.4910 (4)0.5224 (2)0.0402 (6)
C190.8626 (2)0.5844 (3)0.5929 (2)0.0371 (6)
C200.9663 (3)0.6695 (4)0.5973 (2)0.0474 (7)
C211.0233 (3)0.7637 (4)0.6644 (2)0.0539 (8)
C220.9800 (3)0.7778 (4)0.7318 (2)0.0543 (8)
C230.8817 (3)0.6956 (4)0.7306 (2)0.0471 (7)
C240.8200 (2)0.5964 (3)0.6621 (2)0.0356 (6)
C250.7176 (3)0.5108 (3)0.6589 (2)0.0381 (6)
C260.6565 (2)0.4206 (3)0.5903 (2)0.0339 (5)
H30.21060.11080.27570.0560*
H40.29140.10690.16870.0608*
H50.46080.03880.18510.0575*
H60.54610.17640.30830.0515*
H130.14790.10440.38750.0520*
H140.10040.08550.51020.0627*
H150.21520.07180.61950.0661*
H160.37210.20850.60500.0539*
H180.82710.48280.47720.0483*
H200.99620.66050.55310.0568*
H211.09080.81860.66540.0647*
H221.01830.84320.77740.0651*
H230.85440.70510.77600.0566*
H250.69070.51590.70470.0457*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0341 (1)0.0339 (1)0.0272 (1)0.00362 (8)0.01012 (8)0.00112 (7)
O10.043 (1)0.047 (1)0.036 (1)0.0028 (9)0.0176 (9)0.0045 (9)
O20.036 (1)0.047 (1)0.037 (1)0.0050 (9)0.0143 (8)0.0032 (9)
N10.040 (1)0.036 (1)0.031 (1)0.005 (1)0.0129 (9)0.0030 (9)
N20.038 (1)0.034 (1)0.032 (1)0.0074 (9)0.0126 (9)0.0026 (9)
C20.038 (1)0.037 (1)0.031 (1)0.007 (1)0.012 (1)0.003 (1)
C30.046 (2)0.054 (2)0.038 (2)0.003 (1)0.011 (1)0.008 (1)
C40.058 (2)0.061 (2)0.031 (1)0.008 (2)0.011 (1)0.008 (1)
C50.059 (2)0.055 (2)0.034 (1)0.012 (2)0.022 (1)0.003 (1)
C60.048 (2)0.045 (2)0.042 (2)0.003 (1)0.023 (1)0.004 (1)
C120.036 (1)0.035 (1)0.032 (1)0.007 (1)0.011 (1)0.004 (1)
C130.040 (2)0.044 (2)0.047 (2)0.000 (1)0.016 (1)0.001 (1)
C140.047 (2)0.057 (2)0.060 (2)0.002 (1)0.029 (2)0.006 (2)
C150.064 (2)0.069 (2)0.043 (2)0.005 (2)0.033 (2)0.003 (2)
C160.053 (2)0.052 (2)0.033 (1)0.005 (1)0.017 (1)0.003 (1)
C170.037 (1)0.034 (1)0.034 (1)0.007 (1)0.012 (1)0.003 (1)
C180.041 (2)0.042 (2)0.042 (1)0.005 (1)0.020 (1)0.003 (1)
C190.033 (1)0.035 (1)0.042 (1)0.006 (1)0.011 (1)0.007 (1)
C200.036 (1)0.049 (2)0.056 (2)0.002 (1)0.013 (1)0.009 (1)
C210.039 (2)0.052 (2)0.062 (2)0.005 (1)0.005 (2)0.011 (2)
C220.050 (2)0.050 (2)0.049 (2)0.007 (1)0.002 (2)0.001 (1)
C230.051 (2)0.048 (2)0.036 (1)0.000 (1)0.006 (1)0.001 (1)
C240.036 (1)0.032 (1)0.035 (1)0.004 (1)0.005 (1)0.005 (1)
C250.043 (1)0.042 (1)0.031 (1)0.002 (1)0.013 (1)0.001 (1)
C260.034 (1)0.033 (1)0.035 (1)0.006 (1)0.012 (1)0.004 (1)
Geometric parameters (Å, º) top
Pd1—O11.981 (3)C14—C151.377 (4)
Pd1—O21.984 (2)C14—H140.93
Pd1—N12.003 (2)C15—C161.370 (6)
Pd1—N22.001 (3)C15—H150.93
O1—C171.341 (3)C16—H160.93
O2—C261.330 (4)C17—C181.370 (4)
N1—C21.350 (4)C17—C261.444 (5)
N1—C61.345 (4)C18—C191.416 (4)
N2—C121.358 (3)C18—H180.93
N2—C161.334 (4)C19—C201.420 (4)
C2—C31.385 (4)C19—C241.423 (5)
C2—C121.476 (5)C20—C211.362 (4)
C3—C41.376 (6)C20—H200.93
C3—H30.93C21—C221.401 (6)
C4—C51.376 (5)C21—H210.93
C4—H40.93C22—C231.365 (5)
C5—C61.373 (4)C22—H220.93
C5—H50.93C23—C241.416 (4)
C6—H60.93C23—H230.93
C12—C131.380 (5)C24—C251.413 (4)
C13—C141.382 (5)C25—C261.373 (4)
C13—H130.93C25—H250.93
Pd1···C26i3.391 (2)N2···C19i3.495 (3)
Pd1···C12ii3.414 (2)N2···C24i3.583 (3)
Pd1···N2ii3.425 (2)C2···C23i3.385 (4)
Pd1···C25i3.534 (3)C2···C24i3.541 (4)
O1···C4iii3.222 (4)C3···C23i3.496 (5)
O1···C13ii3.306 (4)C3···C21v3.544 (4)
O1···C14ii3.342 (4)C6···C16ii3.470 (4)
O1···C5iii3.365 (4)C12···C24i3.433 (4)
O1···O2i3.554 (3)C12···C23i3.555 (4)
O1···C12ii3.574 (4)C12···C19i3.574 (4)
O2···C2ii3.352 (3)C13···C17ii3.316 (4)
O2···C3ii3.408 (4)C13···C21i3.473 (4)
O2···C5iv3.448 (5)C13···C20i3.579 (5)
N1···C16ii3.511 (4)C14···C20i3.549 (4)
N1···C25i3.517 (4)C16···C18i3.469 (4)
N1···N2ii3.546 (3)
O1—Pd1—O284.84 (9)C15—C14—H14120.4
O1—Pd1—N197.06 (9)C14—C15—C16119.7 (3)
O1—Pd1—N2177.54 (9)C14—C15—H15120.2
O2—Pd1—N1177.58 (10)C16—C15—H15120.2
O2—Pd1—N297.29 (9)N2—C16—C15121.8 (3)
N1—Pd1—N280.78 (9)N2—C16—H16119.2
Pd1—O1—C17110.0 (2)C15—C16—H16119.1
Pd1—O2—C26110.3 (2)O1—C17—C18122.8 (3)
Pd1—N1—C2115.2 (2)O1—C17—C26117.5 (2)
Pd1—N1—C6125.7 (2)C18—C17—C26119.7 (3)
C2—N1—C6119.2 (2)C17—C18—C19121.5 (3)
Pd1—N2—C12115.3 (2)C17—C18—H18119.3
Pd1—N2—C16125.5 (2)C19—C18—H18119.2
C12—N2—C16119.2 (3)C18—C19—C20122.8 (3)
N1—C2—C3121.1 (3)C18—C19—C24119.0 (3)
N1—C2—C12114.7 (2)C20—C19—C24118.1 (3)
C3—C2—C12124.2 (3)C19—C20—C21121.9 (4)
C2—C3—C4119.0 (3)C19—C20—H20119.0
C2—C3—H3120.5C21—C20—H20119.1
C4—C3—H3120.4C20—C21—C22119.9 (3)
C3—C4—C5119.9 (3)C20—C21—H21120.0
C3—C4—H4120.1C22—C21—H21120.1
C5—C4—H4120.0C21—C22—C23120.0 (3)
C4—C5—C6118.7 (4)C21—C22—H22120.0
C4—C5—H5120.7C23—C22—H22120.0
C6—C5—H5120.6C22—C23—C24121.8 (3)
N1—C6—C5122.1 (3)C22—C23—H23119.1
N1—C6—H6118.8C24—C23—H23119.0
C5—C6—H6119.1C19—C24—C23118.2 (3)
N2—C12—C2114.0 (2)C19—C24—C25118.7 (3)
N2—C12—C13121.5 (3)C23—C24—C25123.1 (3)
C2—C12—C13124.5 (3)C24—C25—C26122.1 (3)
C12—C13—C14118.7 (3)C24—C25—H25118.9
C12—C13—H13120.7C26—C25—H25119.0
C14—C13—H13120.6O2—C26—C17117.4 (2)
C13—C14—C15119.2 (3)O2—C26—C25123.7 (3)
C13—C14—H14120.4C17—C26—C25119.0 (3)
Pd1—O1—C17—C18179.8 (2)N2—C16—C15—C141.6 (5)
Pd1—O1—C17—C260.3 (3)C2—N1—C6—C50.3 (4)
Pd1—O2—C26—C172.0 (3)C2—C3—C4—C50.0 (5)
Pd1—O2—C26—C25177.9 (2)C2—C12—N2—C16179.3 (2)
Pd1—N1—C2—C3179.8 (2)C2—C12—C13—C14177.7 (3)
Pd1—N1—C2—C120.1 (3)C3—C2—N1—C60.2 (4)
Pd1—N1—C6—C5179.8 (2)C3—C2—C12—C132.0 (4)
Pd1—N2—C12—C20.2 (3)C3—C4—C5—C60.0 (5)
Pd1—N2—C12—C13178.1 (2)C4—C3—C2—C12179.9 (3)
Pd1—N2—C16—C15176.9 (3)C6—N1—C2—C12179.8 (2)
O1—Pd1—O2—C261.7 (2)C12—N2—C16—C152.0 (4)
O1—Pd1—N1—C2178.8 (2)C12—C13—C14—C150.8 (5)
O1—Pd1—N1—C61.1 (3)C13—C12—N2—C161.0 (4)
O1—C17—C18—C19178.6 (3)C13—C14—C15—C160.2 (5)
O1—C17—C26—O21.2 (3)C17—C18—C19—C20178.8 (3)
O1—C17—C26—C25178.7 (2)C17—C18—C19—C240.2 (4)
O2—Pd1—O1—C171.1 (2)C17—C26—C25—C240.2 (4)
O2—Pd1—N2—C12178.4 (2)C18—C17—C26—C251.7 (4)
O2—Pd1—N2—C160.6 (3)C18—C19—C20—C21177.4 (3)
O2—C26—C17—C18178.4 (3)C18—C19—C24—C23177.5 (3)
O2—C26—C25—C24179.7 (2)C18—C19—C24—C251.7 (4)
N1—Pd1—O1—C17179.6 (2)C19—C18—C17—C261.9 (4)
N1—Pd1—N2—C120.1 (2)C19—C20—C21—C220.3 (5)
N1—Pd1—N2—C16179.1 (3)C19—C24—C23—C220.4 (4)
N1—C2—C3—C40.1 (4)C19—C24—C25—C261.9 (4)
N1—C2—C12—N20.2 (3)C20—C19—C24—C231.5 (4)
N1—C2—C12—C13178.0 (3)C20—C19—C24—C25179.3 (2)
N1—C6—C5—C40.2 (5)C20—C21—C22—C230.8 (5)
N2—Pd1—O2—C26179.6 (2)C21—C20—C19—C241.5 (4)
N2—Pd1—N1—C20.0 (2)C21—C22—C23—C240.8 (5)
N2—Pd1—N1—C6179.9 (3)C22—C23—C24—C25179.6 (3)
N2—C12—C2—C3179.7 (3)C23—C24—C25—C26177.3 (3)
N2—C12—C13—C140.4 (4)C23—C24—C25—C26177.3 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x1, y+1/2, z1/2.
(II) top
Crystal data top
[Pd(C10H6O2)(C18H12N2)]F(000) = 1048.0
Mr = 520.86Dx = 1.638 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ynCell parameters from 18 reflections
a = 9.859 (5) Åθ = 10.6–13.2°
b = 19.67 (1) ŵ = 0.91 mm1
c = 10.922 (5) ÅT = 296 K
β = 94.33 (4)°Prism, colorless
V = 2112.0 (18) Å30.20 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.044
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 012
Tmin = 0.917, Tmax = 0.998k = 025
5278 measured reflectionsl = 1414
4849 independent reflections3 standard reflections every 150 reflections
2647 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0556P)2 + ]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135(Δ/σ)max = 0.001
S = 0.98Δρmax = 1.14 e Å3
4849 reflectionsΔρmin = 0.67 e Å3
298 parameters
Crystal data top
[Pd(C10H6O2)(C18H12N2)]V = 2112.0 (18) Å3
Mr = 520.86Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.859 (5) ŵ = 0.91 mm1
b = 19.67 (1) ÅT = 296 K
c = 10.922 (5) Å0.20 × 0.20 × 0.20 mm
β = 94.33 (4)°
Data collection top
Rigaku AFC-5R
diffractometer
2647 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.044
Tmin = 0.917, Tmax = 0.9983 standard reflections every 150 reflections
5278 measured reflections intensity decay: 0.2%
4849 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044298 parameters
wR(F2) = 0.135H-atom parameters constrained
S = 0.98Δρmax = 1.14 e Å3
4849 reflectionsΔρmin = 0.67 e Å3
Special details top

Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.78287 (4)0.01197 (2)0.97950 (4)0.0382 (1)
O10.8559 (4)0.0125 (2)1.1546 (3)0.0477 (9)
O20.8948 (4)0.0951 (2)0.9690 (3)0.0470 (9)
N10.6515 (4)0.0677 (2)0.9880 (4)0.041 (1)
N20.6829 (4)0.0194 (2)0.8098 (4)0.0392 (10)
C20.5462 (5)0.0632 (3)0.9026 (5)0.043 (1)
C30.4356 (6)0.1075 (3)0.8990 (6)0.050 (1)
C40.4335 (7)0.1577 (3)0.9848 (6)0.060 (2)
C50.5433 (6)0.1664 (3)1.0712 (6)0.050 (1)
C60.5491 (7)0.2198 (3)1.1587 (6)0.061 (2)
C70.6585 (8)0.2287 (3)1.2369 (6)0.062 (2)
C80.7701 (7)0.1841 (3)1.2367 (6)0.061 (2)
C90.7683 (6)0.1302 (3)1.1557 (5)0.049 (1)
C100.6547 (6)0.1204 (3)1.0717 (5)0.045 (1)
C120.5607 (5)0.0102 (3)0.8078 (5)0.042 (1)
C130.4546 (6)0.0050 (3)0.7189 (6)0.052 (1)
C140.4794 (6)0.0484 (3)0.6264 (6)0.056 (2)
C150.6118 (6)0.0745 (3)0.6175 (5)0.048 (1)
C160.6471 (7)0.1131 (3)0.5143 (5)0.056 (2)
C170.7770 (8)0.1333 (3)0.5052 (6)0.062 (2)
C180.8772 (6)0.1182 (3)0.6002 (6)0.056 (2)
C190.8466 (6)0.0829 (3)0.7031 (5)0.045 (1)
C200.7135 (5)0.0597 (3)0.7119 (5)0.042 (1)
C210.9487 (5)0.0619 (3)1.1745 (5)0.038 (1)
C221.0208 (6)0.0713 (3)1.2843 (5)0.043 (1)
C231.1226 (5)0.1221 (3)1.3005 (5)0.040 (1)
C241.2024 (6)0.1333 (3)1.4123 (6)0.052 (1)
C251.2995 (7)0.1836 (4)1.4239 (6)0.061 (2)
C261.3220 (6)0.2250 (4)1.3249 (6)0.063 (2)
C271.2484 (7)0.2162 (3)1.2165 (6)0.056 (2)
C281.1450 (5)0.1658 (3)1.1986 (5)0.042 (1)
C291.0638 (6)0.1576 (3)1.0871 (5)0.043 (1)
C300.9708 (5)0.1066 (3)1.0743 (5)0.039 (1)
H30.36410.10280.83890.0596*
H40.35820.18610.98550.0716*
H60.47530.24911.16190.0738*
H70.66110.26481.29200.0747*
H80.84560.19101.29160.0731*
H90.84200.10061.15630.0593*
H130.36890.01410.72340.0624*
H140.40940.06080.56910.0666*
H160.58060.12440.45280.0671*
H170.80040.15710.43650.0739*
H180.96620.13240.59300.0677*
H190.91340.07440.76600.0538*
H221.00300.04381.35030.0515*
H241.18850.10601.47960.0621*
H251.35010.18971.49830.0733*
H261.38770.25891.33300.0756*
H271.26630.24411.15090.0675*
H291.07420.18731.02230.0514*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0375 (2)0.0372 (2)0.0399 (2)0.0015 (2)0.0021 (2)0.0010 (2)
O10.053 (2)0.045 (2)0.044 (2)0.009 (2)0.003 (2)0.001 (2)
O20.052 (2)0.049 (2)0.039 (2)0.012 (2)0.005 (2)0.002 (2)
N10.043 (2)0.039 (3)0.042 (3)0.001 (2)0.004 (2)0.006 (2)
N20.041 (2)0.038 (2)0.039 (2)0.007 (2)0.003 (2)0.003 (2)
C20.037 (3)0.044 (3)0.048 (3)0.006 (2)0.001 (2)0.015 (2)
C30.036 (3)0.052 (4)0.060 (4)0.002 (3)0.002 (3)0.012 (3)
C40.051 (4)0.049 (4)0.081 (5)0.020 (3)0.017 (3)0.008 (3)
C50.053 (4)0.041 (3)0.056 (4)0.007 (3)0.011 (3)0.005 (3)
C60.077 (5)0.038 (3)0.072 (4)0.015 (3)0.021 (4)0.001 (3)
C70.088 (5)0.051 (4)0.050 (4)0.011 (4)0.015 (4)0.012 (3)
C80.073 (4)0.052 (4)0.056 (4)0.001 (3)0.005 (3)0.003 (3)
C90.052 (3)0.045 (3)0.051 (3)0.008 (3)0.002 (3)0.004 (3)
C100.052 (3)0.037 (3)0.049 (3)0.000 (3)0.017 (3)0.005 (3)
C120.042 (3)0.042 (3)0.044 (3)0.002 (2)0.004 (2)0.012 (3)
C130.045 (3)0.059 (4)0.052 (3)0.002 (3)0.000 (3)0.010 (3)
C140.046 (3)0.072 (4)0.046 (4)0.009 (3)0.009 (3)0.002 (3)
C150.051 (3)0.046 (3)0.047 (3)0.005 (3)0.001 (3)0.002 (3)
C160.070 (4)0.062 (4)0.036 (3)0.009 (3)0.001 (3)0.002 (3)
C170.086 (5)0.054 (4)0.046 (4)0.000 (4)0.013 (4)0.014 (3)
C180.058 (4)0.062 (4)0.051 (4)0.007 (3)0.016 (3)0.004 (3)
C190.047 (3)0.048 (3)0.041 (3)0.002 (3)0.007 (2)0.006 (3)
C200.048 (3)0.040 (3)0.038 (3)0.006 (2)0.006 (2)0.005 (2)
C210.035 (3)0.034 (3)0.045 (3)0.005 (2)0.003 (2)0.002 (2)
C220.053 (3)0.041 (3)0.036 (3)0.004 (3)0.008 (2)0.004 (2)
C230.045 (3)0.033 (3)0.040 (3)0.007 (2)0.001 (2)0.005 (2)
C240.047 (3)0.056 (4)0.051 (4)0.004 (3)0.008 (3)0.002 (3)
C250.058 (4)0.071 (5)0.052 (4)0.005 (3)0.010 (3)0.009 (3)
C260.047 (4)0.074 (5)0.066 (4)0.017 (3)0.005 (3)0.012 (4)
C270.059 (4)0.053 (4)0.057 (4)0.010 (3)0.005 (3)0.003 (3)
C280.039 (3)0.042 (3)0.045 (3)0.003 (2)0.004 (2)0.011 (2)
C290.048 (3)0.039 (3)0.042 (3)0.001 (2)0.004 (3)0.005 (2)
C300.039 (3)0.039 (3)0.039 (3)0.003 (2)0.004 (2)0.003 (2)
Geometric parameters (Å, º) top
Pd1—O11.992 (4)C14—C151.412 (8)
Pd1—O21.982 (4)C14—H140.93
Pd1—N12.039 (4)C15—C161.424 (9)
Pd1—N22.037 (4)C15—C201.413 (8)
O1—C211.341 (6)C16—C171.35 (1)
O2—C301.344 (6)C16—H160.93
N1—C21.345 (7)C17—C181.409 (9)
N1—C101.381 (7)C17—H170.93
N2—C121.337 (7)C18—C191.375 (9)
N2—C201.383 (7)C18—H180.93
C2—C31.395 (8)C19—C201.399 (8)
C2—C121.484 (8)C19—H190.93
C3—C41.362 (9)C21—C221.360 (7)
C3—H30.93C21—C301.432 (8)
C4—C51.392 (9)C22—C231.416 (8)
C4—H40.93C22—H220.93
C5—C61.418 (9)C23—C241.420 (8)
C5—C101.424 (8)C23—C281.437 (8)
C6—C71.335 (10)C24—C251.375 (9)
C6—H60.93C24—H240.93
C7—C81.407 (10)C25—C261.385 (10)
C7—H70.93C25—H250.93
C8—C91.380 (9)C26—C271.352 (9)
C8—H80.93C26—H260.93
C9—C101.406 (8)C27—C281.426 (8)
C9—H90.93C27—H270.93
C12—C131.405 (8)C28—C291.414 (7)
C13—C141.359 (9)C29—C301.360 (7)
C13—H130.93C29—H290.93
Pd1···C3i3.219 (6)C2···C2i3.44 (1)
Pd1···C30ii3.449 (5)C6···C28iii3.407 (9)
Pd1···C21ii3.552 (5)C6···C27iii3.557 (10)
O1···C3i3.442 (7)C6···C23iii3.586 (8)
O1···C13i3.470 (7)C9···C29ii3.275 (8)
O1···O2ii3.584 (6)C10···C13i3.451 (8)
O2···C4i3.534 (8)C10···C29ii3.461 (8)
N1···C29ii3.467 (7)C13···C16iv3.536 (9)
N1···C2i3.493 (7)C14···C14iv3.40 (1)
N1···C12i3.523 (7)C19···C22ii3.302 (8)
N1···C28ii3.538 (7)
O1—Pd1—O283.6 (2)C15—C14—H14120.0
O1—Pd1—N198.4 (2)C14—C15—C16122.1 (5)
O1—Pd1—N2171.1 (2)C14—C15—C20118.8 (5)
O2—Pd1—N1174.4 (2)C16—C15—C20119.0 (5)
O2—Pd1—N297.0 (2)C15—C16—C17120.2 (6)
N1—Pd1—N280.3 (2)C15—C16—H16119.9
Pd1—O1—C21110.6 (3)C17—C16—H16119.9
Pd1—O2—C30111.4 (3)C16—C17—C18120.0 (6)
Pd1—N1—C2112.2 (3)C16—C17—H17120.0
Pd1—N1—C10128.6 (3)C18—C17—H17120.0
C2—N1—C10119.0 (5)C17—C18—C19121.6 (6)
Pd1—N2—C12110.9 (3)C17—C18—H18119.2
Pd1—N2—C20128.8 (3)C19—C18—H18119.2
C12—N2—C20119.0 (4)C18—C19—C20119.0 (5)
N1—C2—C3122.7 (5)C18—C19—H19120.5
N1—C2—C12114.8 (5)C20—C19—H19120.5
C3—C2—C12122.4 (5)N2—C20—C15119.9 (5)
C2—C3—C4119.1 (5)N2—C20—C19120.0 (5)
C2—C3—H3120.5C15—C20—C19120.1 (5)
C4—C3—H3120.5O1—C21—C22123.1 (5)
C3—C4—C5120.3 (6)O1—C21—C30117.5 (4)
C3—C4—H4119.8C22—C21—C30119.4 (5)
C5—C4—H4119.8C21—C22—C23121.6 (5)
C4—C5—C6122.6 (6)C21—C22—H22119.2
C4—C5—C10118.9 (5)C23—C22—H22119.2
C6—C5—C10118.5 (5)C22—C23—C24124.0 (5)
C5—C6—C7121.1 (6)C22—C23—C28118.3 (5)
C5—C6—H6119.4C24—C23—C28117.7 (5)
C7—C6—H6119.4C23—C24—C25121.9 (6)
C6—C7—C8120.8 (6)C23—C24—H24119.1
C6—C7—H7119.6C25—C24—H24119.0
C8—C7—H7119.6C24—C25—C26120.2 (6)
C7—C8—C9120.5 (6)C24—C25—H25119.9
C7—C8—H8119.7C26—C25—H25119.9
C9—C8—H8119.7C25—C26—C27120.1 (6)
C8—C9—C10119.6 (6)C25—C26—H26120.0
C8—C9—H9120.2C27—C26—H26120.0
C10—C9—H9120.2C26—C27—C28122.7 (6)
N1—C10—C5119.8 (5)C26—C27—H27118.6
N1—C10—C9120.8 (5)C28—C27—H27118.6
C5—C10—C9119.4 (5)C23—C28—C27117.4 (5)
N2—C12—C2115.4 (4)C23—C28—C29119.2 (5)
N2—C12—C13122.8 (5)C27—C28—C29123.4 (5)
C2—C12—C13121.8 (5)C28—C29—C30120.4 (5)
C12—C13—C14118.8 (5)C28—C29—H29119.8
C12—C13—H13120.6C30—C29—H29119.8
C14—C13—H13120.6O2—C30—C21116.4 (4)
C13—C14—C15120.0 (5)O2—C30—C29122.7 (5)
C13—C14—H14120.0C21—C30—C29120.9 (5)
Pd1—O1—C21—C22176.0 (4)C3—C2—C12—C139.6 (9)
Pd1—O1—C21—C304.3 (5)C3—C4—C5—C6176.9 (6)
Pd1—O2—C30—C215.3 (6)C3—C4—C5—C102.8 (9)
Pd1—O2—C30—C29174.9 (4)C4—C3—C2—C12175.8 (6)
Pd1—N1—C2—C3172.7 (4)C4—C5—C6—C7177.0 (7)
Pd1—N1—C2—C1211.0 (6)C4—C5—C10—C9177.7 (6)
Pd1—N1—C10—C5171.9 (4)C5—C6—C7—C81 (1)
Pd1—N1—C10—C99.8 (8)C5—C10—C9—C80.3 (9)
Pd1—N2—C12—C223.6 (6)C6—C5—C10—C92.0 (9)
Pd1—N2—C12—C13159.2 (5)C6—C7—C8—C90 (1)
Pd1—N2—C20—C15159.8 (4)C7—C6—C5—C102.7 (10)
Pd1—N2—C20—C1923.5 (7)C7—C8—C9—C100.8 (10)
O1—Pd1—O2—C306.0 (3)C10—N1—C2—C12172.7 (5)
O1—Pd1—N1—C2152.7 (4)C12—N2—C20—C156.3 (7)
O1—Pd1—N1—C1023.1 (5)C12—N2—C20—C19170.4 (5)
O1—C21—C22—C23177.0 (5)C12—C13—C14—C153.3 (9)
O1—C21—C30—O20.7 (7)C13—C12—N2—C209.1 (8)
O1—C21—C30—C29179.6 (5)C13—C14—C15—C16171.9 (6)
O2—Pd1—O1—C215.5 (3)C13—C14—C15—C205.8 (9)
O2—Pd1—N2—C12152.3 (4)C14—C15—C16—C17175.5 (6)
O2—Pd1—N2—C2014.7 (5)C14—C15—C20—C19177.7 (5)
O2—C30—C21—C22179.0 (5)C15—C16—C17—C182.2 (10)
O2—C30—C29—C28177.6 (5)C15—C20—C19—C181.9 (8)
N1—Pd1—O1—C21179.7 (3)C16—C15—C20—C190.1 (8)
N1—Pd1—N2—C1222.8 (4)C16—C17—C18—C190.2 (10)
N1—Pd1—N2—C20170.2 (5)C17—C16—C15—C202.2 (9)
N1—C2—C3—C40.2 (9)C17—C18—C19—C201.9 (9)
N1—C2—C12—N28.6 (7)C21—C22—C23—C24178.9 (5)
N1—C2—C12—C13174.2 (5)C21—C22—C23—C282.4 (8)
N1—C10—C5—C40.6 (9)C21—C30—C29—C282.7 (8)
N1—C10—C5—C6179.6 (5)C22—C21—C30—C290.8 (8)
N1—C10—C9—C8178.6 (6)C22—C23—C24—C25179.5 (6)
N2—Pd1—O2—C30177.0 (3)C22—C23—C28—C27179.6 (5)
N2—Pd1—N1—C218.3 (4)C22—C23—C28—C291.0 (8)
N2—Pd1—N1—C10165.8 (5)C23—C22—C21—C303.3 (8)
N2—C12—C2—C3167.6 (5)C23—C24—C25—C260.0 (10)
N2—C12—C13—C144.4 (9)C23—C28—C27—C261.7 (9)
N2—C20—C15—C141.0 (8)C23—C28—C29—C303.6 (8)
N2—C20—C15—C16176.7 (5)C24—C23—C28—C271.6 (8)
N2—C20—C19—C18174.8 (5)C24—C23—C28—C29177.7 (5)
C2—N1—C10—C53.7 (8)C24—C25—C26—C270 (1)
C2—N1—C10—C9174.6 (5)C25—C24—C23—C280.9 (9)
C2—C3—C4—C53.0 (9)C25—C26—C27—C280 (1)
C2—C12—N2—C20168.0 (5)C26—C27—C28—C29177.7 (6)
C2—C12—C13—C14172.6 (6)C27—C28—C29—C30177.1 (5)
C3—C2—N1—C103.6 (8)C27—C28—C29—C30177.1 (5)
Symmetry codes: (i) x+1, y, z+2; (ii) x+2, y, z+2; (iii) x+3/2, y1/2, z+5/2; (iv) x+1, y, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formula[Pd(C10H6O2)(C10H8N2)][Pd(C10H6O2)(C18H12N2)]
Mr420.75520.86
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)296296
a, b, c (Å)12.117 (2), 8.239 (2), 16.857 (1)9.859 (5), 19.67 (1), 10.922 (5)
β (°) 108.804 (8) 94.33 (4)
V3)1593.1 (5)2112.0 (18)
Z44
Radiation typeMo KαMo Kα
µ (mm1)1.180.91
Crystal size (mm)0.50 × 0.20 × 0.200.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Rigaku AFC-5R
diffractometer
Absorption correctionψ scan
(North, Phillips & Mathews, 1968)
ψ scan
(North et al., 1968)
Tmin, Tmax0.936, 1.0000.917, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
4095, 3658, 3090 5278, 4849, 2647
Rint0.0140.044
(sin θ/λ)max1)0.6500.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.078, 1.14 0.044, 0.135, 0.98
No. of reflections36584849
No. of parameters226298
No. of restraints??
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.881.14, 0.67

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992), TEXSAN (Molecular Structure Corporation, 2000), SIR97 (Altomare et al., 1999), SHELXS97 (Scheldrick, 1997), SHELXL97 (Scheldrick, 1997), ORTEPII (Johnson, 1976).

Selected geometric parameters (Å, º) for (I) top
Pd1—O11.981 (3)Pd1—N12.003 (2)
Pd1—O21.984 (2)Pd1—N22.001 (3)
O1—Pd1—O284.84 (9)O2—Pd1—N1177.58 (10)
O1—Pd1—N197.06 (9)O2—Pd1—N297.29 (9)
O1—Pd1—N2177.54 (9)N1—Pd1—N280.78 (9)
Selected geometric parameters (Å, º) for (II) top
Pd1—O11.992 (4)Pd1—N12.039 (4)
Pd1—O21.982 (4)Pd1—N22.037 (4)
O1—Pd1—O283.6 (2)O2—Pd1—N1174.4 (2)
O1—Pd1—N198.4 (2)O2—Pd1—N297.0 (2)
O1—Pd1—N2171.1 (2)N1—Pd1—N280.3 (2)
 

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