(1,1-Cyclo­butane­dicarboxyl­ato-κ2O,O′)(2,2′-biquinoline-κ2N,N′)palladium(II) monohydrate

Okabe, N.; Muranishi, Y.; Odoko, M.

doi:10.1107/S160053680502965X

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(1,1-Cyclobutanedicarboxylato-κ²O,O′)(2,2′-biquinoline-κ²N,N′)palladium(II) monohydrate

N. Okabe, Y. Muranishi and M. Odoko

In the title compound, [Pd(C₆H₆O₄)(C₁₈H₁₂N₂)]·H₂O, the Pd^II atom has a distorted cis-planar four-coordination geometry defined by two O atoms of a bidentate 1,1-cyclobutanedicarboxylate anion and two N atoms of the 2,2′-biquinoline ligand. In the crystal structure, centrosymmetric clusters of the complex molecules and water molecules are formed through O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502965X/lh6500sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680502965X/lh6500Isup2.hkl Contains datablock I

CCDC reference: 287635

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.027
wR factor = 0.075
Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The cis-square planar coordinated Pt^II complexes such as cisplatin, cis-diamminedichloroplatinum(II), carboplatin, cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II), and oxaliplatin, trans-l-1,2-diaminocyclohexane platinum(II) oxalate, are well known anticancer drugs. Carboplatin with a bidentate 1,1-cyclobutanedicarboxylato (cbdca) ligand has fewer side effects than cisplatin (Jakupec et al., 2003). Pd^II analogues of Pt^II complexes have been used as good models for studies of the chemistry of square planar complexes (Rau & van Eldik, 1996). For example, cis-diammine(1,1-cyclobutanedicarboxylate)palladium(II) (Barnham et al., 1994) is isostructural with carboplatin (Beagley et al., 1985; Neidle et al., 1980). Recently, the palladium complex with the aromatic heterocyclic ligand [Pd(bpy)(cbdca)] (bpy = 2,2'-bipyridine) has been shown to have better cytotoxic activity than cisplatin against P₃₈₈ lymphocytic leukemia cells (Mansuri-Torshizi et al., 2001). Aromatic heterocycles can stack with nucleobases and enhance complex formation with DNA, which is the principal target in the chemotherapy of tumors (Shehata, 2001).

In a previous study (Muranishi & Okabe, 2004), we determined the structures of the carboplatin analogues of Pd^II complexes with N,N'-bidentate aromatic heterocycle ligands bipyridine(bpy), [Pd(bpy)(cbdca)], and 1,10-phenanthroline (phen), [Pd(phen)(cbdca)]·H₂O and [Pd(phen)(cbdca)]·2H₂O. Because biq (biq = 2,2'-biquinoline) is an aromatic heterocyclic compound with interesting characteristics, such as inhibition activity against the formation of an abnormal prion protein (Murakami-Kubo et al., 2004) and mutagenic activity as the rhodamin(III) complex (Sadiq & Zaghal, 1996), we present in this study the structure of [Pd(biq)(cbdca)]·H₂O, (I).

The central Pd atom of (I) has a distorted cis-square planar coordination geometry, from two N atoms of biq and two O atoms of the cbdca ligand (Fig. 1). The overall structure of (I) resembles those of [Pd(bpy)(cbdca)], (II), [Pd(phen)(cbdca)]·H₂O, (IIIa), and [Pd(phen)(cbdca)]·2H₂O, (IIIb) (Muranishi & Okabe, 2004). The bond lengths and bond angles in (I) are similar to those in (II), (IIIa) and (IIIb) and selected values are compared in Table 2. The Pd atom makes a six-membered chelate ring with cbdca in a boat conformation, and a five-membered chelate ring with biq in an envelope conformation, in which the deviation of atom Pd1 from the N1/C2/C12/N12 plane is 0.671 (4) Å. The biq group is non-planar, with a dihedral angle of 20.5 (1)° between the two quinoline rings. The cyclobutane best least-squares plane is almost perpendicular to the N1—C2—C12—N12 plane in biq, with a dihedral angle of 86.8 (2)°.

The N—Pd—N chelate angle in (I), as well as in (II), (IIIa) and (IIIb), is smaller than those in the ethylenediamine (en) ligand in [Pd(en)(cbdca)] [84.15 (8)°; Tercero et al., 2003] or the NH₃ ligand in [Pd(NH₃)₂(cbdca)] [95.0°; Barnham et al., 1994]. In the crystal structure, centrosymmetric clusters of the title complex and water molecules are formed through O—H···O hydrogen bonds (Table 1).

Experimental top

Biq (5.0 mg) dissolved in dimethylformamide (DMF, 2 ml) was reacted with palladium acetate, [Pd(CH₃COOH)₂] (4.4 mg), dissolved in DMF (2 ml) for 15 min at room temperature (molar ratio of 1:1), and then an equimolar amount of 1,1-cyclobutanedicarboxylic acid dissolved in DMF (1 ml) was added with stirring. This mixture was left to stand at room temperature, and yellow plate-like crystals appeared in a few days.

Computing details top

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

Figures top

Fig. 1. Molecular structure of (I), with the atom numbering scheme. Ellipsoids for non-H atoms correspond to 50% probability.

(I) top

Crystal data top

[Pd(C₆H₆O₄)(C₁₈H₁₂N₂)]·H₂O	Z = 2
M_r = 522.84	F(000) = 528.0
Triclinic, P1	D_x = 1.661 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 10.363 (2) Å	Cell parameters from 25 reflections
b = 10.438 (2) Å	θ = 14.9–15.0°
c = 11.450 (2) Å	µ = 0.93 mm⁻¹
α = 64.66 (1)°	T = 296 K
β = 80.87 (2)°	Plate, yellow
γ = 69.07 (1)°	0.35 × 0.15 × 0.10 mm
V = 1045.5 (4) Å³

Data collection top

Rigaku AFC-5R diffractometer	R_int = 0.025
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −13→12
T_min = 0.846, T_max = 0.911	k = −13→0
5074 measured reflections	l = −14→13
4809 independent reflections	3 standard reflections every 150 reflections
4179 reflections with I > 2σ(I)	intensity decay: 0.9%

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.027	(Δ/σ)_max = −0.001
wR(F²) = 0.075	Δρ_max = 0.32 e Å⁻³
S = 1.22	Δρ_min = −0.44 e Å⁻³
4809 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
289 parameters	Extinction coefficient: 0.0000
H-atom parameters constrained

Crystal data top

[Pd(C₆H₆O₄)(C₁₈H₁₂N₂)]·H₂O	γ = 69.07 (1)°
M_r = 522.84	V = 1045.5 (4) Å³
Triclinic, P1	Z = 2
a = 10.363 (2) Å	Mo Kα radiation
b = 10.438 (2) Å	µ = 0.93 mm⁻¹
c = 11.450 (2) Å	T = 296 K
α = 64.66 (1)°	0.35 × 0.15 × 0.10 mm
β = 80.87 (2)°

Data collection top

Rigaku AFC-5R diffractometer	4179 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.025
T_min = 0.846, T_max = 0.911	3 standard reflections every 150 reflections
5074 measured reflections	intensity decay: 0.9%
4809 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	289 parameters
wR(F²) = 0.075	H-atom parameters constrained
S = 1.22	Δρ_max = 0.32 e Å⁻³
4809 reflections	Δρ_min = −0.44 e Å⁻³

Special details top

Refinement. Refinement using reflections with F² > 0.0 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

	x	y	z	U_iso*/U_eq
Pd1	0.59719 (2)	0.04981 (2)	0.73035 (2)	0.03718 (7)
O1	0.4545 (2)	0.2526 (2)	0.6685 (2)	0.0485 (4)
O2	0.3562 (3)	0.4752 (2)	0.6705 (3)	0.0841 (8)
O3	0.7284 (2)	0.1440 (2)	0.7417 (2)	0.0521 (4)
O4	0.7750 (2)	0.3157 (3)	0.7729 (3)	0.0756 (7)
O5	0.8360 (4)	0.4829 (5)	0.4991 (3)	0.129 (1)
N1	0.4894 (2)	−0.0551 (2)	0.6893 (2)	0.0383 (4)
N2	0.7446 (2)	−0.1512 (2)	0.7653 (2)	0.0405 (4)
C2	0.5767 (3)	−0.1670 (3)	0.6585 (2)	0.0411 (5)
C3	0.5302 (3)	−0.2415 (3)	0.6060 (2)	0.0482 (6)
C4	0.3929 (3)	−0.2031 (3)	0.5880 (2)	0.0521 (6)
C5	0.2977 (3)	−0.0904 (3)	0.6237 (2)	0.0484 (6)
C6	0.1524 (3)	−0.0479 (4)	0.6108 (3)	0.0637 (8)
C7	0.0653 (3)	0.0593 (4)	0.6477 (3)	0.0714 (9)
C8	0.1159 (3)	0.1309 (4)	0.7001 (3)	0.0684 (8)
C9	0.2551 (3)	0.0943 (3)	0.7153 (3)	0.0557 (6)
C10	0.3488 (3)	−0.0157 (3)	0.6752 (2)	0.0420 (5)
C12	0.7220 (3)	−0.2171 (3)	0.6962 (2)	0.0423 (5)
C13	0.8259 (3)	−0.3304 (3)	0.6705 (3)	0.0581 (7)
C14	0.9527 (3)	−0.3809 (4)	0.7219 (3)	0.0687 (9)
C15	0.9770 (3)	−0.3265 (3)	0.8060 (3)	0.0590 (7)
C16	1.1029 (3)	−0.3846 (4)	0.8727 (4)	0.080 (1)
C17	1.1179 (4)	−0.3328 (4)	0.9567 (4)	0.084 (1)
C18	1.0111 (3)	−0.2198 (4)	0.9799 (4)	0.0726 (9)
C19	0.8877 (3)	−0.1565 (3)	0.9160 (3)	0.0569 (7)
C20	0.8685 (3)	−0.2089 (3)	0.8279 (3)	0.0467 (5)
C21	0.4441 (3)	0.3523 (3)	0.7112 (3)	0.0481 (6)
C22	0.6928 (3)	0.2561 (3)	0.7747 (3)	0.0466 (6)
C23	0.5433 (3)	0.3116 (3)	0.8159 (2)	0.0390 (5)
C24	0.5143 (3)	0.4283 (3)	0.8740 (2)	0.0475 (6)
C25	0.4961 (5)	0.3126 (3)	1.0072 (3)	0.079 (1)
C26	0.5095 (3)	0.1995 (3)	0.9513 (3)	0.0506 (6)
H3	0.5931	−0.3169	0.5834	0.0578*
H4	0.3616	−0.2514	0.5520	0.0625*
H5A	0.8154	0.4234	0.5790	0.0659*
H5B	0.7621	0.4902	0.4527	0.0659*
H6	0.1173	−0.0948	0.5765	0.0765*
H7	−0.0294	0.0861	0.6383	0.0856*
H8	0.0541	0.2047	0.7252	0.0821*
H9	0.2872	0.1417	0.7517	0.0668*
H13	0.8086	−0.3710	0.6188	0.0697*
H14	1.0243	−0.4524	0.7010	0.0825*
H16	1.1761	−0.4595	0.8579	0.0963*
H17	1.2011	−0.3731	1.0001	0.1013*
H18	1.0233	−0.1866	1.0396	0.0871*
H19	0.8175	−0.0795	0.9310	0.0683*
H24A	0.5922	0.4617	0.8677	0.0569*
H24B	0.4310	0.5130	0.8412	0.0569*
H25A	0.4064	0.3431	1.0459	0.0943*
H25B	0.5695	0.2806	1.0666	0.0943*
H26A	0.4241	0.1801	0.9534	0.0607*
H26B	0.5850	0.1066	0.9873	0.0607*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0376 (1)	0.0374 (1)	0.0422 (1)	−0.01009 (7)	0.00060 (7)	−0.02307 (8)
O1	0.052 (1)	0.0418 (9)	0.057 (1)	−0.0043 (8)	−0.0148 (8)	−0.0283 (8)
O2	0.097 (2)	0.049 (1)	0.107 (2)	0.013 (1)	−0.053 (2)	−0.044 (1)
O3	0.0403 (9)	0.057 (1)	0.075 (1)	−0.0171 (8)	0.0048 (8)	−0.042 (1)
O4	0.061 (1)	0.091 (2)	0.116 (2)	−0.042 (1)	0.017 (1)	−0.069 (2)
O5	0.140 (3)	0.168 (3)	0.093 (2)	−0.055 (3)	−0.019 (2)	−0.056 (2)
N1	0.045 (1)	0.0376 (10)	0.0355 (9)	−0.0135 (8)	−0.0004 (8)	−0.0170 (8)
N2	0.041 (1)	0.039 (1)	0.042 (1)	−0.0111 (8)	0.0042 (8)	−0.0190 (8)
C2	0.054 (1)	0.035 (1)	0.034 (1)	−0.017 (1)	0.0032 (10)	−0.0130 (9)
C3	0.070 (2)	0.039 (1)	0.042 (1)	−0.022 (1)	0.000 (1)	−0.019 (1)
C4	0.077 (2)	0.050 (1)	0.041 (1)	−0.034 (1)	−0.005 (1)	−0.016 (1)
C5	0.058 (2)	0.053 (1)	0.039 (1)	−0.030 (1)	−0.002 (1)	−0.011 (1)
C6	0.063 (2)	0.083 (2)	0.059 (2)	−0.043 (2)	−0.003 (1)	−0.024 (2)
C7	0.045 (2)	0.100 (3)	0.071 (2)	−0.031 (2)	−0.001 (1)	−0.030 (2)
C8	0.045 (2)	0.085 (2)	0.073 (2)	−0.015 (2)	0.004 (1)	−0.036 (2)
C9	0.047 (1)	0.065 (2)	0.060 (2)	−0.016 (1)	0.000 (1)	−0.033 (1)
C10	0.045 (1)	0.046 (1)	0.036 (1)	−0.019 (1)	−0.0004 (9)	−0.0139 (10)
C12	0.050 (1)	0.037 (1)	0.040 (1)	−0.015 (1)	0.0039 (10)	−0.0163 (10)
C13	0.067 (2)	0.047 (1)	0.062 (2)	−0.010 (1)	0.004 (1)	−0.033 (1)
C14	0.056 (2)	0.056 (2)	0.088 (2)	−0.001 (1)	0.010 (2)	−0.041 (2)
C15	0.042 (1)	0.053 (2)	0.074 (2)	−0.006 (1)	0.002 (1)	−0.027 (1)
C16	0.042 (2)	0.073 (2)	0.115 (3)	0.002 (1)	−0.010 (2)	−0.041 (2)
C17	0.047 (2)	0.088 (3)	0.105 (3)	−0.005 (2)	−0.021 (2)	−0.034 (2)
C18	0.057 (2)	0.084 (2)	0.078 (2)	−0.018 (2)	−0.014 (2)	−0.032 (2)
C19	0.047 (1)	0.063 (2)	0.062 (2)	−0.012 (1)	−0.006 (1)	−0.030 (1)
C20	0.038 (1)	0.046 (1)	0.053 (1)	−0.010 (1)	0.002 (1)	−0.020 (1)
C21	0.054 (1)	0.040 (1)	0.054 (1)	−0.010 (1)	−0.007 (1)	−0.024 (1)
C22	0.050 (1)	0.049 (1)	0.050 (1)	−0.021 (1)	0.000 (1)	−0.026 (1)
C23	0.049 (1)	0.034 (1)	0.040 (1)	−0.0148 (10)	−0.0009 (9)	−0.0185 (9)
C24	0.066 (2)	0.038 (1)	0.046 (1)	−0.019 (1)	0.000 (1)	−0.023 (1)
C25	0.144 (3)	0.051 (2)	0.047 (2)	−0.039 (2)	0.012 (2)	−0.024 (1)
C26	0.070 (2)	0.038 (1)	0.046 (1)	−0.023 (1)	0.005 (1)	−0.017 (1)

Geometric parameters (Å, º) top

PD1—O1	1.995 (2)	C9—H9	0.930
PD1—O3	1.988 (3)	C12—C13	1.390 (4)
PD1—N1	2.037 (3)	C13—C14	1.355 (5)
PD1—N2	2.020 (2)	C13—H13	0.930
O1—C21	1.293 (4)	C14—C15	1.400 (6)
O2—C21	1.216 (3)	C14—H14	0.930
O3—C22	1.294 (4)	C15—C16	1.418 (5)
O4—C22	1.215 (5)	C15—C20	1.422 (4)
O5—H5A	0.903	C16—C17	1.339 (8)
O5—H5B	0.963	C16—H16	0.930
N1—C2	1.343 (3)	C17—C18	1.389 (5)
N1—C10	1.381 (3)	C17—H17	0.930
N2—C12	1.339 (4)	C18—C19	1.373 (5)
N2—C20	1.376 (3)	C18—H18	0.930
C2—C3	1.399 (5)	C19—C20	1.404 (6)
C2—C12	1.476 (4)	C19—H19	0.930
C3—C4	1.358 (5)	C21—C23	1.522 (4)
C3—H3	0.930	C22—C23	1.523 (3)
C4—C5	1.406 (4)	C23—C24	1.543 (4)
C4—H4	0.930	C23—C26	1.569 (3)
C5—C6	1.423 (4)	C24—C25	1.522 (4)
C5—C10	1.423 (5)	C24—H24A	0.970
C6—C7	1.344 (6)	C24—H24B	0.970
C6—H6	0.930	C25—C26	1.525 (6)
C7—C8	1.399 (7)	C25—H25A	0.970
C7—H7	0.930	C25—H25B	0.970
C8—C9	1.374 (4)	C26—H26A	0.970
C8—H8	0.930	C26—H26B	0.970
C9—C10	1.409 (4)

PD1···C4ⁱ	3.296 (3)	O5···C13ⁱⁱⁱ	3.276 (7)
O1···C3ⁱ	3.172 (4)	O5···C14^vii	3.348 (5)
O1···C4ⁱ	3.262 (4)	O5···C21ⁱⁱ	3.505 (5)
O1···O5ⁱⁱ	3.425 (4)	O5···O5^viii	3.548 (9)
O2···O5ⁱⁱ	2.794 (6)	N1···C25^ix	3.347 (3)
O2···C4ⁱⁱⁱ	3.225 (4)	N1···C3ⁱ	3.444 (3)
O2···C16^iv	3.552 (5)	N1···C4ⁱ	3.554 (3)
O3···C7^v	3.398 (4)	C2···C25^ix	3.529 (4)
O4···C18^vi	3.451 (5)	C2···C10ⁱ	3.566 (3)
O4···C8^v	3.532 (4)	C3···C24^x	3.538 (3)
O4···C17^vi	3.544 (6)	C3···C10ⁱ	3.587 (3)
O4···C13ⁱⁱⁱ	3.576 (5)	C24···C25^xi	3.476 (6)

O1—PD1—O3	88.20 (8)	C15—C14—H14	119.7
O1—PD1—N1	96.49 (9)	C14—C15—C16	123.5 (3)
O1—PD1—N2	171.53 (9)	C14—C15—C20	118.3 (3)
O3—PD1—N1	168.17 (8)	C16—C15—C20	118.2 (4)
O3—PD1—N2	93.51 (9)	C15—C16—C17	120.8 (3)
N1—PD1—N2	80.31 (9)	C15—C16—H16	119.6
PD1—O1—C21	123.2 (2)	C17—C16—H16	119.6
PD1—O3—C22	123.9 (2)	C16—C17—C18	121.0 (4)
H5A—O5—H5B	98.5	C16—C17—H17	119.5
PD1—N1—C2	110.1 (2)	C18—C17—H17	119.5
PD1—N1—C10	129.4 (2)	C17—C18—C19	120.9 (4)
C2—N1—C10	119.9 (3)	C17—C18—H18	119.5
PD1—N2—C12	110.7 (1)	C19—C18—H18	119.5
PD1—N2—C20	128.5 (2)	C18—C19—C20	119.4 (3)
C12—N2—C20	119.7 (2)	C18—C19—H19	120.3
N1—C2—C3	121.9 (2)	C20—C19—H19	120.3
N1—C2—C12	115.9 (3)	N2—C20—C15	119.5 (3)
C3—C2—C12	122.0 (2)	N2—C20—C19	120.9 (2)
C2—C3—C4	119.7 (3)	C15—C20—C19	119.6 (3)
C2—C3—H3	120.2	O1—C21—O2	121.2 (3)
C4—C3—H3	120.2	O1—C21—C23	118.4 (2)
C3—C4—C5	120.1 (3)	O2—C21—C23	120.4 (3)
C3—C4—H4	119.9	O3—C22—O4	121.5 (3)
C5—C4—H4	119.9	O3—C22—C23	117.6 (3)
C4—C5—C6	122.9 (4)	O4—C22—C23	120.8 (3)
C4—C5—C10	118.7 (3)	C21—C23—C22	111.0 (2)
C6—C5—C10	118.5 (3)	C21—C23—C24	115.7 (2)
C5—C6—C7	120.8 (4)	C21—C23—C26	112.7 (2)
C5—C6—H6	119.6	C22—C23—C24	114.5 (3)
C7—C6—H6	119.6	C22—C23—C26	112.4 (2)
C6—C7—C8	120.6 (3)	C24—C23—C26	88.9 (2)
C6—C7—H7	119.7	C23—C24—C25	90.2 (2)
C8—C7—H7	119.7	C23—C24—H24A	113.6
C7—C8—C9	121.3 (3)	C23—C24—H24B	113.6
C7—C8—H8	119.3	C25—C24—H24A	113.6
C9—C8—H8	119.3	C25—C24—H24B	113.6
C8—C9—C10	119.3 (4)	H24A—C24—H24B	110.9
C8—C9—H9	120.4	C24—C25—C26	91.3 (2)
C10—C9—H9	120.4	C24—C25—H25A	113.4
N1—C10—C5	119.7 (2)	C24—C25—H25B	113.4
N1—C10—C9	120.7 (3)	C26—C25—H25A	113.4
C5—C10—C9	119.6 (3)	C26—C25—H25B	113.4
N2—C12—C2	114.4 (2)	H25A—C25—H25B	110.7
N2—C12—C13	122.2 (3)	C23—C26—C25	89.1 (2)
C2—C12—C13	123.3 (3)	C23—C26—H26A	113.8
C12—C13—C14	119.1 (4)	C23—C26—H26B	113.8
C12—C13—H13	120.5	C25—C26—H26A	113.8
C14—C13—H13	120.5	C25—C26—H26B	113.8
C13—C14—C15	120.6 (3)	H26A—C26—H26B	111.0
C13—C14—H14	119.7

PD1—O1—C21—O2	179.5 (2)	N2—C12—C13—C14	3.1 (4)
PD1—O1—C21—C23	−1.5 (3)	N2—C20—C15—C14	−0.8 (4)
PD1—O3—C22—O4	−175.5 (2)	N2—C20—C15—C16	−179.5 (3)
PD1—O3—C22—C23	4.3 (3)	N2—C20—C19—C18	178.0 (3)
PD1—N1—C2—C3	−169.4 (2)	C2—N1—C10—C5	−2.3 (3)
PD1—N1—C2—C12	16.9 (2)	C2—N1—C10—C9	175.6 (2)
PD1—N1—C10—C5	168.7 (2)	C2—C3—C4—C5	−0.9 (3)
PD1—N1—C10—C9	−13.4 (3)	C2—C12—N2—C20	166.9 (2)
PD1—N2—C12—C2	−24.4 (2)	C2—C12—C13—C14	−172.3 (2)
PD1—N2—C12—C13	159.8 (2)	C3—C2—N1—C10	3.2 (3)
PD1—N2—C20—C15	−158.9 (2)	C3—C2—C12—C13	7.0 (3)
PD1—N2—C20—C19	23.0 (3)	C3—C4—C5—C6	−178.2 (2)
O1—PD1—O3—C22	35.1 (2)	C3—C4—C5—C10	1.7 (3)
O1—PD1—N1—C2	148.9 (1)	C4—C3—C2—C12	171.7 (2)
O1—PD1—N1—C10	−22.8 (2)	C4—C5—C6—C7	179.2 (3)
O1—C21—C23—C22	54.4 (3)	C4—C5—C10—C9	−178.0 (2)
O1—C21—C23—C24	−173.0 (2)	C5—C6—C7—C8	−0.3 (4)
O1—C21—C23—C26	−72.7 (3)	C5—C10—C9—C8	−2.0 (4)
O2—C21—C23—C22	−126.6 (3)	C6—C5—C10—C9	1.8 (3)
O2—C21—C23—C24	6.0 (4)	C6—C7—C8—C9	0.1 (5)
O2—C21—C23—C26	106.2 (3)	C7—C6—C5—C10	−0.6 (4)
O3—PD1—O1—C21	−36.5 (2)	C7—C8—C9—C10	1.1 (4)
O3—PD1—N1—C2	36.0 (4)	C10—N1—C2—C12	−170.5 (2)
O3—PD1—N1—C10	−135.7 (3)	C12—N2—C20—C15	7.6 (3)
O3—PD1—N2—C12	−143.7 (2)	C12—N2—C20—C19	−170.5 (2)
O3—PD1—N2—C20	23.8 (2)	C12—C13—C14—C15	3.9 (4)
O3—C22—C23—C21	−55.9 (3)	C13—C12—N2—C20	−8.9 (3)
O3—C22—C23—C24	170.9 (2)	C13—C14—C15—C16	173.7 (3)
O3—C22—C23—C26	71.4 (3)	C13—C14—C15—C20	−4.9 (4)
O4—C22—C23—C21	123.9 (3)	C14—C15—C16—C17	−176.8 (3)
O4—C22—C23—C24	−9.3 (3)	C14—C15—C20—C19	177.3 (3)
O4—C22—C23—C26	−108.8 (3)	C15—C16—C17—C18	−0.7 (6)
N1—PD1—O1—C21	154.4 (2)	C15—C20—C19—C18	−0.1 (4)
N1—PD1—O3—C22	148.7 (3)	C16—C15—C20—C19	−1.4 (4)
N1—PD1—N2—C12	26.2 (2)	C16—C17—C18—C19	−0.9 (6)
N1—PD1—N2—C20	−166.4 (2)	C17—C16—C15—C20	1.8 (5)
N1—C2—C3—C4	−1.6 (3)	C17—C18—C19—C20	1.3 (5)
N1—C2—C12—N2	4.9 (3)	C21—C23—C24—C25	120.1 (3)
N1—C2—C12—C13	−179.3 (2)	C21—C23—C26—C25	−122.8 (3)
N1—C10—C5—C4	−0.1 (3)	C22—C23—C24—C25	−108.9 (3)
N1—C10—C5—C6	179.7 (2)	C22—C23—C26—C25	110.8 (3)
N1—C10—C9—C8	−179.9 (2)	C23—C24—C25—C26	−5.5 (3)
N2—PD1—O3—C22	−153.2 (2)	C23—C26—C25—C24	5.4 (3)
N2—PD1—N1—C2	−23.2 (1)	C24—C23—C26—C25	−5.3 (2)
N2—PD1—N1—C10	165.1 (2)	C25—C24—C23—C26	5.3 (3)
N2—C12—C2—C3	−168.8 (2)	C25—C24—C23—C26	5.3 (3)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x−1, y+1, z; (v) x+1, y, z; (vi) −x+2, −y, −z+2; (vii) −x+2, −y, −z+1; (viii) −x+2, −y+1, −z+1; (ix) −x+1, −y, −z+2; (x) x, y−1, z; (xi) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4	0.90	2.07	2.958 (4)	169.00
O5—H5B···O2ⁱⁱ	0.96	1.85	2.794 (6)	166.3

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Pd(C₆H₆O₄)(C₁₈H₁₂N₂)]·H₂O
M_r	522.84
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.363 (2), 10.438 (2), 11.450 (2)
α, β, γ (°)	64.66 (1), 80.87 (2), 69.07 (1)
V (Å³)	1045.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.35 × 0.15 × 0.10

Data collection
Diffractometer	Rigaku AFC-5R diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.846, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	5074, 4809, 4179
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.075, 1.22
No. of reflections	4809
No. of parameters	289
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.44

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4	0.90	2.07	2.958 (4)	169.00
O5—H5B···O2ⁱ	0.96	1.85	2.794 (6)	166.3

Symmetry code: (i) −x+1, −y+1, −z+1.

Comparative selected geometric parameters (Å, °). top

	(I)	(II)ⁱ	(IIIa)ⁱ	(IIIb)ⁱ
Pd1—O1	1.995 (2)	2.002 (2)	2.003 (4)	2.001 (3)
Pd1—O3	1.988 (3)	2.004 (2)	2.005 (4)	1.982 (3)
Pd1—N1	2.037 (3)	1.999 (2)	1.991 (5)	2.002 (4)
Pd1—N2	2.020 (2)	1.998 (2)	1.994 (5)	2.010 (4)

O1—Pd1—O3	88.20 (8)	91.68 (7)	91.3 (2)	92.8 (1)
O1—Pd1—N1	96.49 (9)	93.94 (8)	93.0 (2)	93.3 (1)
O1—Pd1—N2	171.53 (9)	174.40 (6)	173.2 (2)	174.7 (1)
O3—Pd1—N1	168.17 (8)	174.37 (9)	174.7 (2)	172.7 (2)
O3—Pd1—N2	93.51 (9)	93.57 (8)	93.2 (2)	91.6 (1)
N1—Pd1—N2	80.31 (9)	80.80 (8)	82.2 (2)	82.1 (1)

Note: (i) From Muranishi & Okabe (2004).

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