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

Okabe, N.; Aziyama, T.; Odoko, M.

doi:10.1107/S160053680503062X

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

In the title complex, [Pd(C₆H₄O₂)(C₁₈H₁₂N₂)], the central Pd atom has a distorted cis-planar four-coordination geometry defined by two O atoms of a 1,2-benzenediolate dianion and two N atoms of a 2,2′-biquinoline ligand. The overall structure of the complex is not planar, with a dihedral angle of 136.23 (8)° between the quinoline and benzenediolate mean planes.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503062X/hb6273sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680503062X/hb6273Isup2.hkl Contains datablock I

CCDC reference: 287586

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.032
wR factor = 0.089
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio

   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

A large number of investigations have focused on the design of palladium(II) or platinum(II) complexes because of their biological significance in areas such as antitumor, antimicrovial and antiviral activity (Corbi et al., 2005; Giovagnini et al., 2005).

Palladium complexes with aromatic ligands and cis-square planar coordination geometry has been intensively studied because of their cytotoxic activity (Mansuri-Torshizi et al., 2001; Afrasiabi et al., 2004; Rebolledo et al., 2005; Padhye et al., 2005) or DNA binding properties (Cusumano & Giannetto, 1997; Tercero et al., 2003), which is the principal target in the chemotherapy of tumors (Shehata, 2001; Cusumano & Giannetto, 1997; Neidle et al., 1987).

As an extension of these studies, we have synthesized and determined the crystal structures of a number of cis-coordinated palladium complexes with aromatic ligands including Pd(bpy)(cbdca) and Pb(phen)(cbdca) (Muranishi & Okabe, 2004), Pd(phen)(ca) (Okabe et al., 2003), Pd(bpy)(nad) and Pd(biq)(nad) (Okabe et al., 2004) and Pd(bpy)(ca) (Okabe et al., 2005), where bpy is 2,2'-bipyridine, cbdca is 1,1-cyclobutanedicarboxylate, phen is 1,10-phenanthroline, nad is 2,3-naphthalenediol, biq is biquinoline and ca is catechol or 1,2-benzenediol.

In this study, the title compound, Pd(biq)(ca), (I), has been synthesized and its structure determined. In complex (I), the central Pd atom has a distorted cis-square planar coordination geometry arising from the two N atoms of biq and the two O atoms of ca (Fig. 1).

The overall structure is not planar and resembles that of Pd(biq)(nad), (II) (Okabe et al., 2004), which has the same biq moiety as (I) and two analogous anionic O atoms of the 2,3-naphthalenediol moiety. The dihedral angle between the biq and ca best planes in (I) is 136.23 (8)°, with an equivalent value for (II) of 148.73 (7)° (where a dihedral angle of 180° indicates a flat structure). This shows that the distortion of (I) from the planar conformation is larger than in (II).

The Pd—X (X = N, O) bond lengths and angles in (I) are similar to those of (II) (Table 1). This resemblance suggests similar coordination bond strength in both complexes.

Experimental top

First, biq (5.0 mg dissolved in 2 ml dimethylformamide, DMF) was reacted with palladium acetate, Pd(CH₃COOH)₂ (4.4 mg in 2 ml DMF) for 15 min at room temperature (molar ratio of 1:1). An equimolar amount of ca dissolved to DMF was then added with stirring. This mixture was left to stand at room temperature and yielded red plate-shaped crystals of (I) over a period of 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. The molecular structure of (I), showing 50% displacement ellipsoids for the non-H atoms.

(1,2-Benzenediolato-κ²O,O')((2,2'-biquinoline-κ²N,N')palladium(II) top

Crystal data top

[Pd(C₆H₄O₂)(C₁₈H₁₂N₂)]	F(000) = 944.0
M_r = 470.81	D_x = 1.686 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.042 (2) Å	θ = 14.4–15.0°
b = 9.487 (2) Å	µ = 1.02 mm⁻¹
c = 17.796 (2) Å	T = 296 K
β = 95.635 (10)°	Plate, blue
V = 1855.2 (6) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Rigaku AFC-5R diffractometer	R_int = 0.043
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→14
T_min = 0.832, T_max = 0.903	k = 0→12
4749 measured reflections	l = −23→23
4267 independent reflections	3 standard reflections every 150 reflections
2996 reflections with I > 2σ(I)	intensity decay: 0.4%

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0349P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max = 0.002
S = 1.07	Δρ_max = 0.47 e Å⁻³
4267 reflections	Δρ_min = −0.35 e Å⁻³
262 parameters

Crystal data top

[Pd(C₆H₄O₂)(C₁₈H₁₂N₂)]	V = 1855.2 (6) Å³
M_r = 470.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.042 (2) Å	µ = 1.02 mm⁻¹
b = 9.487 (2) Å	T = 296 K
c = 17.796 (2) Å	0.20 × 0.15 × 0.10 mm
β = 95.635 (10)°

Data collection top

Rigaku AFC-5R diffractometer	2996 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.043
T_min = 0.832, T_max = 0.903	3 standard reflections every 150 reflections
4749 measured reflections	intensity decay: 0.4%
4267 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	262 parameters
wR(F²) = 0.089	H-atom parameters constrained
S = 1.07	Δρ_max = 0.47 e Å⁻³
4267 reflections	Δρ_min = −0.35 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Pd1	0.05885 (2)	0.11461 (2)	0.63043 (1)	0.03864 (9)
O1	0.0582 (2)	−0.0464 (3)	0.7018 (1)	0.0486 (6)
O2	0.2308 (2)	0.1338 (2)	0.6746 (1)	0.0477 (6)
N1	−0.1090 (2)	0.0813 (3)	0.5725 (1)	0.0363 (6)
N2	0.0631 (2)	0.2649 (3)	0.5482 (2)	0.0409 (6)
C2	−0.1195 (3)	0.1450 (4)	0.5050 (2)	0.0387 (7)
C3	−0.2194 (3)	0.1224 (4)	0.4512 (2)	0.0474 (8)
C4	−0.3056 (3)	0.0267 (4)	0.4649 (2)	0.0486 (9)
C5	−0.2987 (3)	−0.0417 (4)	0.5348 (2)	0.0425 (8)
C6	−0.3882 (3)	−0.1396 (4)	0.5528 (2)	0.057 (1)
C7	−0.3828 (4)	−0.1980 (5)	0.6223 (2)	0.062 (1)
C8	−0.2884 (3)	−0.1644 (4)	0.6768 (2)	0.0534 (9)
C9	−0.1985 (3)	−0.0728 (4)	0.6616 (2)	0.0458 (8)
C10	−0.2007 (3)	−0.0094 (3)	0.5898 (2)	0.0391 (7)
C12	−0.0208 (3)	0.2425 (3)	0.4903 (2)	0.0404 (7)
C13	−0.0154 (4)	0.3061 (4)	0.4196 (2)	0.0487 (8)
C14	0.0775 (4)	0.3945 (4)	0.4086 (2)	0.0553 (9)
C15	0.1649 (4)	0.4264 (4)	0.4684 (2)	0.0531 (9)
C16	0.2619 (4)	0.5215 (4)	0.4608 (3)	0.072 (1)
C17	0.3390 (4)	0.5557 (5)	0.5219 (4)	0.092 (2)
C18	0.3237 (5)	0.4990 (5)	0.5931 (4)	0.098 (2)
C19	0.2333 (4)	0.4036 (4)	0.6023 (3)	0.075 (1)
C20	0.1538 (3)	0.3630 (3)	0.5397 (2)	0.0496 (9)
C21	0.1731 (3)	−0.0774 (4)	0.7297 (2)	0.0401 (7)
C22	0.2017 (3)	−0.2026 (4)	0.7679 (2)	0.0485 (9)
C23	0.3229 (3)	−0.2311 (4)	0.7931 (2)	0.0530 (9)
C24	0.4124 (3)	−0.1369 (4)	0.7801 (2)	0.0519 (9)
C25	0.3840 (3)	−0.0112 (4)	0.7418 (2)	0.0503 (9)
C26	0.2644 (3)	0.0181 (4)	0.7160 (2)	0.0411 (7)
H3	−0.2263	0.1731	0.4062	0.0569*
H4	−0.3689	0.0065	0.4281	0.0583*
H6	−0.4512	−0.1639	0.5166	0.0690*
H7	−0.4427	−0.2612	0.6337	0.0748*
H8	−0.2864	−0.2049	0.7245	0.0641*
H9	−0.1357	−0.0523	0.6987	0.0549*
H13	−0.0754	0.2878	0.3804	0.0585*
H14	0.0831	0.4340	0.3613	0.0663*
H16	0.2725	0.5603	0.4139	0.0858*
H17	0.4029	0.6176	0.5166	0.1110*
H18	0.3758	0.5266	0.6348	0.1179*
H19	0.2245	0.3660	0.6498	0.0894*
H22	0.1408	−0.2666	0.7765	0.0582*
H23	0.3429	−0.3146	0.8188	0.0636*
H24	0.4929	−0.1569	0.7970	0.0623*
H25	0.4452	0.0526	0.7335	0.0604*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0411 (1)	0.0347 (1)	0.0389 (1)	−0.0002 (1)	−0.0022 (1)	−0.0016 (1)
O1	0.041 (1)	0.052 (1)	0.051 (1)	−0.003 (1)	−0.002 (1)	0.011 (1)
O2	0.047 (1)	0.038 (1)	0.055 (1)	−0.007 (1)	−0.009 (1)	0.006 (1)
N1	0.038 (1)	0.036 (1)	0.035 (1)	0.004 (1)	0.004 (1)	−0.003 (1)
N2	0.042 (2)	0.034 (1)	0.046 (2)	0.003 (1)	0.001 (1)	−0.001 (1)
C2	0.041 (2)	0.041 (2)	0.035 (2)	0.007 (1)	0.006 (1)	−0.005 (1)
C3	0.047 (2)	0.059 (2)	0.035 (2)	0.002 (2)	0.002 (1)	−0.002 (2)
C4	0.042 (2)	0.063 (2)	0.040 (2)	0.001 (2)	−0.002 (2)	−0.008 (2)
C5	0.038 (2)	0.044 (2)	0.046 (2)	0.003 (2)	0.006 (1)	−0.006 (2)
C6	0.043 (2)	0.068 (3)	0.060 (2)	−0.011 (2)	0.001 (2)	−0.003 (2)
C7	0.053 (2)	0.062 (3)	0.073 (3)	−0.015 (2)	0.012 (2)	0.007 (2)
C8	0.051 (2)	0.055 (2)	0.055 (2)	−0.001 (2)	0.009 (2)	0.008 (2)
C9	0.043 (2)	0.048 (2)	0.046 (2)	0.004 (2)	0.001 (2)	0.002 (2)
C10	0.036 (2)	0.037 (2)	0.045 (2)	0.007 (1)	0.008 (1)	−0.005 (1)
C12	0.046 (2)	0.035 (2)	0.041 (2)	0.007 (1)	0.005 (1)	−0.005 (1)
C13	0.060 (2)	0.048 (2)	0.039 (2)	−0.005 (2)	0.005 (2)	−0.001 (2)
C14	0.070 (3)	0.048 (2)	0.051 (2)	−0.002 (2)	0.017 (2)	0.001 (2)
C15	0.052 (2)	0.034 (2)	0.074 (3)	0.003 (2)	0.014 (2)	0.000 (2)
C16	0.060 (3)	0.048 (2)	0.109 (4)	−0.006 (2)	0.021 (3)	0.012 (2)
C17	0.058 (3)	0.048 (3)	0.168 (6)	−0.013 (2)	−0.005 (3)	0.029 (3)
C18	0.085 (4)	0.054 (3)	0.143 (5)	−0.027 (3)	−0.052 (3)	0.031 (3)
C19	0.080 (3)	0.044 (2)	0.092 (3)	−0.015 (2)	−0.032 (3)	0.021 (2)
C20	0.044 (2)	0.030 (2)	0.073 (3)	0.003 (1)	−0.003 (2)	0.003 (2)
C21	0.040 (2)	0.045 (2)	0.034 (2)	−0.001 (1)	−0.001 (1)	−0.002 (1)
C22	0.049 (2)	0.050 (2)	0.046 (2)	−0.005 (2)	0.002 (2)	0.008 (2)
C23	0.056 (2)	0.050 (2)	0.051 (2)	0.003 (2)	−0.001 (2)	0.009 (2)
C24	0.049 (2)	0.053 (2)	0.052 (2)	0.004 (2)	−0.007 (2)	0.005 (2)
C25	0.045 (2)	0.050 (2)	0.055 (2)	−0.009 (2)	−0.001 (2)	0.001 (2)
C26	0.049 (2)	0.037 (2)	0.037 (2)	−0.005 (1)	0.000 (1)	−0.002 (1)

Geometric parameters (Å, º) top

Pd1—O1	1.987 (2)	C12—C13	1.402 (5)
Pd1—O2	1.990 (2)	C13—C14	1.353 (6)
Pd1—N1	2.055 (3)	C13—H13	0.930
Pd1—N2	2.047 (3)	C14—C15	1.398 (5)
O1—C21	1.349 (4)	C14—H14	0.930
O2—C26	1.355 (4)	C15—C16	1.417 (6)
N1—C2	1.340 (4)	C15—C20	1.420 (6)
N1—C10	1.386 (4)	C16—C17	1.354 (7)
N2—C12	1.334 (4)	C16—H16	0.930
N2—C20	1.386 (4)	C17—C18	1.402 (9)
C2—C3	1.405 (4)	C17—H17	0.930
C2—C12	1.472 (5)	C18—C19	1.369 (7)
C3—C4	1.355 (5)	C18—H18	0.930
C3—H3	0.930	C19—C20	1.403 (6)
C4—C5	1.398 (5)	C19—H19	0.930
C4—H4	0.930	C21—C22	1.389 (5)
C5—C6	1.416 (5)	C21—C26	1.395 (5)
C5—C10	1.419 (4)	C22—C23	1.396 (5)
C6—C7	1.350 (6)	C22—H22	0.930
C6—H6	0.930	C23—C24	1.369 (5)
C7—C8	1.389 (5)	C23—H23	0.930
C7—H7	0.930	C24—C25	1.394 (5)
C8—C9	1.366 (5)	C24—H24	0.930
C8—H8	0.930	C25—C26	1.383 (5)
C9—C10	1.410 (5)	C25—H25	0.930
C9—H9	0.930

Pd1···C3ⁱ	3.288 (4)	C3···C26ⁱ	3.254 (5)
Pd1···C2ⁱ	3.555 (3)	C3···C21ⁱ	3.336 (5)
O1···C13ⁱ	3.281 (4)	C3···C17ⁱⁱⁱ	3.380 (6)
O1···C3ⁱ	3.471 (4)	C4···C26ⁱ	3.323 (5)
O2···C4ⁱ	3.093 (4)	C4···C6^iv	3.532 (5)
O2···C8ⁱⁱ	3.276 (4)	C8···C26^v	3.561 (5)
O2···C3ⁱ	3.298 (4)	C13···C20ⁱⁱⁱ	3.596 (5)

O1—Pd1—O2	83.19 (9)	C2—C12—C13	121.8 (3)
O1—Pd1—N1	98.19 (10)	C12—C13—C14	119.7 (3)
O1—Pd1—N2	173.8 (1)	C12—C13—H13	120.1
O2—Pd1—N1	172.1 (1)	C14—C13—H13	120.1
O2—Pd1—N2	97.49 (10)	C13—C14—C15	120.0 (4)
N1—Pd1—N2	80.3 (1)	C13—C14—H14	120.0
Pd1—O1—C21	109.9 (2)	C15—C14—H14	120.0
Pd1—O2—C26	109.9 (2)	C14—C15—C16	122.5 (4)
Pd1—N1—C2	112.0 (2)	C14—C15—C20	118.4 (3)
Pd1—N1—C10	128.9 (2)	C16—C15—C20	119.1 (4)
C2—N1—C10	118.6 (3)	C15—C16—C17	119.8 (5)
Pd1—N2—C12	112.2 (2)	C15—C16—H16	120.1
Pd1—N2—C20	127.8 (2)	C17—C16—H16	120.1
C12—N2—C20	118.5 (3)	C16—C17—C18	120.8 (5)
N1—C2—C3	122.4 (3)	C16—C17—H17	119.6
N1—C2—C12	116.3 (3)	C18—C17—H17	119.6
C3—C2—C12	121.3 (3)	C17—C18—C19	121.0 (5)
C2—C3—C4	119.8 (3)	C17—C18—H18	119.5
C2—C3—H3	120.1	C19—C18—H18	119.5
C4—C3—H3	120.1	C18—C19—C20	119.5 (5)
C3—C4—C5	119.6 (3)	C18—C19—H19	120.2
C3—C4—H4	120.2	C20—C19—H19	120.2
C5—C4—H4	120.2	N2—C20—C15	120.5 (3)
C4—C5—C6	121.8 (3)	N2—C20—C19	120.0 (4)
C4—C5—C10	119.0 (3)	C15—C20—C19	119.5 (3)
C6—C5—C10	119.2 (3)	O1—C21—C22	121.8 (3)
C5—C6—C7	120.5 (3)	O1—C21—C26	117.6 (3)
C5—C6—H6	119.8	C22—C21—C26	120.5 (3)
C7—C6—H6	119.8	C21—C22—C23	119.2 (3)
C6—C7—C8	120.5 (4)	C21—C22—H22	120.4
C6—C7—H7	119.7	C23—C22—H22	120.4
C8—C7—H7	119.7	C22—C23—C24	120.3 (3)
C7—C8—C9	121.1 (4)	C22—C23—H23	119.8
C7—C8—H8	119.4	C24—C23—H23	119.9
C9—C8—H8	119.4	C23—C24—C25	120.7 (3)
C8—C9—C10	120.2 (3)	C23—C24—H24	119.7
C8—C9—H9	119.9	C25—C24—H24	119.7
C10—C9—H9	119.9	C24—C25—C26	119.7 (3)
N1—C10—C5	120.4 (3)	C24—C25—H25	120.2
N1—C10—C9	121.2 (3)	C26—C25—H25	120.2
C5—C10—C9	118.5 (3)	O2—C26—C21	117.2 (3)
N2—C12—C2	115.6 (3)	O2—C26—C25	123.0 (3)
N2—C12—C13	122.5 (3)	C21—C26—C25	119.7 (3)

Pd1—O1—C21—C22	−166.0 (3)	C2—N1—C10—C5	4.6 (5)
Pd1—O1—C21—C26	11.1 (3)	C2—N1—C10—C9	−176.1 (3)
Pd1—O2—C26—C21	−9.5 (4)	C2—C3—C4—C5	4.5 (5)
Pd1—O2—C26—C25	167.5 (3)	C2—C12—N2—C20	−175.6 (3)
Pd1—N1—C2—C3	171.4 (3)	C2—C12—C13—C14	−179.6 (3)
Pd1—N1—C2—C12	−9.4 (4)	C3—C2—N1—C10	−0.4 (5)
Pd1—N1—C10—C5	−165.7 (2)	C3—C2—C12—C13	−6.5 (5)
Pd1—N1—C10—C9	13.7 (5)	C3—C4—C5—C6	178.2 (4)
Pd1—N2—C12—C2	17.1 (4)	C3—C4—C5—C10	−0.4 (5)
Pd1—N2—C12—C13	−162.4 (3)	C4—C3—C2—C12	176.6 (3)
Pd1—N2—C20—C15	158.3 (3)	C4—C5—C6—C7	−176.3 (4)
Pd1—N2—C20—C19	−23.8 (5)	C4—C5—C10—C9	176.4 (3)
O1—Pd1—O2—C26	12.0 (2)	C5—C6—C7—C8	−0.9 (6)
O1—Pd1—N1—C2	−159.8 (2)	C5—C10—C9—C8	0.8 (5)
O1—Pd1—N1—C10	11.0 (3)	C6—C5—C10—C9	−2.2 (5)
O1—C21—C22—C23	177.7 (3)	C6—C7—C8—C9	−0.6 (6)
O1—C21—C26—O2	−1.1 (4)	C7—C6—C5—C10	2.3 (6)
O1—C21—C26—C25	−178.2 (3)	C7—C8—C9—C10	0.6 (6)
O2—Pd1—O1—C21	−12.6 (2)	C10—N1—C2—C12	178.8 (3)
O2—Pd1—N2—C12	155.2 (2)	C12—N2—C20—C15	−6.8 (5)
O2—Pd1—N2—C20	−10.6 (3)	C12—N2—C20—C19	171.2 (3)
O2—C26—C21—C22	176.1 (3)	C12—C13—C14—C15	−2.6 (6)
O2—C26—C25—C24	−176.0 (3)	C13—C12—N2—C20	4.9 (5)
N1—Pd1—O1—C21	159.6 (2)	C13—C14—C15—C16	−178.0 (4)
N1—Pd1—N2—C12	−17.1 (2)	C13—C14—C15—C20	0.6 (6)
N1—Pd1—N2—C20	177.1 (3)	C14—C15—C16—C17	175.5 (4)
N1—C2—C3—C4	−4.2 (5)	C14—C15—C20—C19	−173.8 (4)
N1—C2—C12—N2	−5.2 (4)	C15—C16—C17—C18	−0.5 (7)
N1—C2—C12—C13	174.3 (3)	C15—C20—C19—C18	−3.0 (6)
N1—C10—C5—C4	−4.2 (5)	C16—C15—C20—C19	4.8 (6)
N1—C10—C5—C6	177.1 (3)	C16—C17—C18—C19	2.4 (7)
N1—C10—C9—C8	−178.5 (3)	C17—C16—C15—C20	−3.1 (6)
N2—Pd1—O2—C26	−161.8 (2)	C17—C18—C19—C20	−0.7 (7)
N2—Pd1—N1—C2	14.2 (2)	C21—C22—C23—C24	−0.1 (5)
N2—Pd1—N1—C10	−175.1 (3)	C21—C26—C25—C24	1.0 (5)
N2—C12—C2—C3	174.0 (3)	C22—C21—C26—C25	−1.0 (5)
N2—C12—C13—C14	−0.2 (5)	C22—C23—C24—C25	0.1 (6)
N2—C20—C15—C14	4.1 (5)	C23—C22—C21—C26	0.6 (5)
N2—C20—C15—C16	−177.2 (3)	C23—C24—C25—C26	−0.5 (5)
N2—C20—C19—C18	179.1 (4)	C23—C24—C25—C26	−0.5 (5)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) −x, −y+1, −z+1; (iv) −x−1, −y, −z+1; (v) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Pd(C₆H₄O₂)(C₁₈H₁₂N₂)]
M_r	470.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.042 (2), 9.487 (2), 17.796 (2)
β (°)	95.635 (10)
V (Å³)	1855.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Rigaku AFC-5R diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.832, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	4749, 4267, 2996
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.089, 1.07
No. of reflections	4267
No. of parameters	262
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.35

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).

Comparative selected geometric parameters (Å, °) top

	(I)	(II)ⁱ
Pd1—O1	1.987 (2)	1.992 (4)
Pd1—O2	1.990 (2)	1.982 (4)
Pd1—N1	2.055 (3)	2.039 (4)
Pd1—N2	2.047 (2)	2.037 (4)

O1—Pd1—O2	83.19 (9)	83.6 (2)
O1—Pd1—N1	98.19 (10)	98.4 (2)
O1—Pd1—N2	173.8 (1)	171.1 (2)
O2—Pd1—N1	172.1 (1)	174.4 (2)
O2—Pd1—N2	97.49 (10)	97.0 (2)
N1—Pd1—N2	80.3 (1)	80.3 (2)

Note: (i) Okabe et al. (2004).

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

Supporting information

Key indicators

checkCIF/PLATON results

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