trans-Bis[3-(2-fluorophenyl)-1-(4-nitrophenyl)triazenido-κN³]bis(pyridine-κN)palladium(II)

In the title complex, [Pd(C₁₂H₈FN₄O₂)₂(C₅H₅N)₂] or trans-[Pd(FC₆H₄N=N—NC₆H₄NO₂)(C₅H₅N)₂], the Pd atom lies on a centre of inversion in space group P. The coordination geometry about the Pd²⁺ ion is square planar, with two deprotonated 3-(2-fluoro­phenyl)-1-(4-nitro­phenyl)­triazenide ions, FC₆H₄N=N—NC₆H₄NO₂⁻, acting as monodentate ligands (two-electron donors), while two neutral pyridine mol­ecules complete the metal coordination sphere. The whole triazenide ligand is not planar, with the largest interplanar angle being 16.8 (5)° between the phenyl ring of the 2-­fluorophenyl group and the plane defined by the N=N—N moiety. The Pd—N(triazenide) and Pd—N(pyridine) distances are 2.021 (3) and 2.039 (3) Å, respectively.

S1. Comment

Although palladium(II) complexes with nitrogen coordination spheres involving catenated 1,3-diaryl-substituted triazenido ligands, ArNNNAr^-, have been investigated over the last few decades, the structures of such compounds continues to attract interest (Moore & Robinson, 1986; Peregudov et al., 1998; Cao et al., 2000). In this work, we report the synthesis and structural characterization of the title complex, (I), a centrosymmetric mononuclear Pd^II complex with an asymmetric disubstituted 1,3-diaryltriazenido ion and pyridine as ligands. \sch

In the molecule of the monomeric complex, (I), with site symmetry 1, the square-planar coordinated Pd²⁺ ion is situated on an inversion centre, with two 3-(2-fluorophenyl)-1-(4-nitrophenyl)triazenido ions, FC₆H₄N═ N—NC₆H₄NO₂^-, and two pyridine molecules coordinated trans to each other (Fig. 1).

The deviation observed in (I) from the normal N—N and C_ar—N bonds makes evident the delocalization of the π electrons on the N11—N12═N13 group towards the terminal aryl substituents. The N12═N13 bond [1.283 (5) Å] is longer than the characteristic value for such a double bond (1.24 Å), whereas N11—N12 [1.325 (5) Å] is shorter than the characteristic value for a single bond (1.44 Å) (International Tables for X-Ray Crystallography, 1985), and both N11—C11 [1.403 (5) Å] and N13—C21 [1.413 (5) Å] are shorter than expected for a C_ar—N single bond. The Pd—N11 bond distance of 2.021 (3) Å is close to the sum of the covalent radii of 2.08 Å (Sheldrick, 1997) and corresponds to a covalent single bond. These values are in good agreement with the distances found in the related compound trans-[Pd(RN1—N2═N3R)Cl(PPh₃)₂] (R is p-toluene?; N2═N3 1.286, N1—N2 1.336 and Pd—N1 2.033 Å; Moore & Robinson, 1986; Bombieri et al., 1975, 1976; Brown & Ibers, 1976).

Due to the delocalization of the π electrons over the nitro group and the C11—C16 phenyl ring, towards the N11—N12═N13 chain, this part of the triazenido ligand is nearly planar [interplanar angles O1/N1/O2/C11—C16 3.0 (6)° and C11—C16/N11—N12═N13 4.2 (4)°]. On the other hand, the C21—C26 ring makes an angle of 16.8 (5)° with the plane defined by the N11—N12═N13 group, which accounts for the significant deviation from planarity of the whole 1,3-diaryltriazenido ligand. The C11—C16 phenyl ring and the 2-fluorophenyl substituent are almost planar (r.m.s. deviations 0.0064 and 0.0042 Å, respectively).

The pyridine ring (N31—C36) is planar to within experimental accuracy (r.m.s. deviation 0.0062 Å), making a dihedral angle of 69.5 (2)° with the N11—Pd—N31ⁱ moiety [symmetry code: (i) -x, -y, -z]. The Pd—N31 bond distance of 2.039 (3) Å is shorter than the sum of the covalent radii (2.08 Å; Sheldrick, 1997) and may be compared with the value found in the compound [Pd(py)₄](I₃)₂ (Pd—N_py 2.014 Å; Tebbe et al., 1996).

S2. Experimental

To a solution of PdCl₂ (17 mg, 0.1 mmol) in concentrated aqueous ammonium hydroxide (5 ml), a mixture of 3-(2-fluorophenyl)-1-(4-nitrophenyl)triazene (50 g, 0.2 mmol) in tetrahydrofuran (30 ml) and concentrated aqueous ammonium hydroxide (1 ml) was slowly added under continuous stirring. After stirring for 1 h at room temperature, pyridine (1 ml) was added to the deep-red reaction mixture, which was then stirred for a further 24 h. Red prism-shaped crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of the solvent mixture at room temperature (yield: 45 mg, 60%; m.p. 525–529 K).

S3. Refinement

H atoms were treated as riding atoms, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

Fig. 1. A perspective view of the molecule of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.

trans-Bis[3-(2-fluorophenyl)-1-(4-nitrophenyl)triazenido-κN³]bis(pyridine- κN)palladium(II)

Crystal data

[Pd(C5H5N)2(C12H8FN4O2)2]	Z = 1
Mr = 783.07	F(000) = 396
Triclinic, P1	Dx = 1.567 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.941 (2) Å	Cell parameters from 25 reflections
b = 9.732 (2) Å	θ = 2.6–25.1°
c = 10.9449 (10) Å	µ = 0.63 mm^−1
α = 110.058 (14)°	T = 293 K
β = 93.437 (13)°	Prism, red
γ = 109.012 (19)°	0.20 × 0.13 × 0.07 mm
V = 829.9 (3) Å^3

Data collection

Enraf Nonius TurboCAD-4 diffractometer	Rint = 0.032
non–profiled ω/2θ scans	θmax = 25.1°, θmin = 2.7°
Absorption correction: ψ-scan (North et al., 1968)	h = 0→10
Tmin = 0.885, Tmax = 0.958	k = −11→10
3149 measured reflections	l = −13→13
2947 independent reflections	3 standard reflections every 120 min
2446 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0476P)^2 where P = (Fo^2 + 2Fc^2)/3
2947 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.98 e Å^−3

Special details

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.

Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.5788 (0.0158) x + 3.8984 (0.0231) y - 3.3162 (0.0235) z = 0.1283 (0.0069)

* -0.0063 (0.0032) N31 * 0.0021 (0.0036) C32 * 0.0063 (0.0041) C33 * -0.0103 (0.0047) C34 * 0.0060 (0.0050) C35 * 0.0022 (0.0042) C36

Rms deviation of fitted atoms = 0.0062

- 2.5738 (0.0306) x + 6.1420 (0.0622) y - 9.9713 (0.0186) z = 0.0511 (0.0630)

Angle to previous plane (with approximate e.s.d.) = 80.07 (0.34)

* 0.0000 (0.0000) O1 * 0.0000 (0.0000) N1 * 0.0000 (0.0000) O2

Rms deviation of fitted atoms = 0.0000

- 2.8753 (0.0153) x + 6.4731 (0.0127) y - 9.7250 (0.0096) z = 0.1027 (0.0074)

Angle to previous plane (with approximate e.s.d.) = 3.02 (0.63)

* 0.0094 (0.0029) C11 * -0.0050 (0.0030) C12 * -0.0041 (0.0031) C13 * 0.0088 (0.0030) C14 * -0.0042 (0.0030) C15 * -0.0049 (0.0030) C16

Rms deviation of fitted atoms = 0.0064

3.4817 (0.0480) x - 6.5938 (0.0167) y + 9.3862 (0.0255) z = 0.0001 (0.0138)

Angle to previous plane (with approximate e.s.d.) = 4.18 (0.42)

* 0.0000 (0.0000) N11 * 0.0000 (0.0000) N12 * 0.0000 (0.0000) N13

Rms deviation of fitted atoms = 0.0000

5.5096 (0.0100) x - 5.6656 (0.0161) y + 8.1117 (0.0112) z = 0.4652 (0.0096)

Angle to previous plane (with approximate e.s.d.) = 16.75 (0.48)

* 0.0023 (0.0035) C21 * -0.0068 (0.0041) C22 * -0.0010 (0.0039) C23 * -0.0008 (0.0038) C24 * 0.0057 (0.0042) C25 * -0.0041 (0.0037) C26 * 0.0047 (0.0028) F

Rms deviation of fitted atoms = 0.0042

- 1.8669 (0.0145) x + 7.5101 (0.0113) y + 3.4136 (0.0185) z = 0.0000 (0.0000)

Angle to previous plane (with approximate e.s.d.) = 89.99 (0.13)

* 0.0000 (0.0000) N11 * 0.0000 (0.0000) N31 * 0.0000 (0.0000) N11_$1 * 0.0000 (0.0000) N31_$1 0.0000 (0.0000) Pd

Rms deviation of fitted atoms = 0.0000

- 1.8669 (0.0145) x + 7.5101 (0.0113) y + 3.4136 (0.0185) z = 0.0000 (0.0000)

Angle to previous plane (with approximate e.s.d.) = 0.00 (0.30)

* 0.0000 (0.0000) N11 * 0.0000 (0.0000) N31 * 0.0000 (0.0000) N11_$1 * 0.0000 (0.0000) N31_$1

Rms deviation of fitted atoms = 0.0000

6.5788 (0.0158) x + 3.8984 (0.0231) y - 3.3162 (0.0235) z = 0.1283 (0.0069)

Angle to previous plane (with approximate e.s.d.) = 69.46 (0.17)

* -0.0063 (0.0032) N31 * 0.0021 (0.0036) C32 * 0.0063 (0.0041) C33 * -0.0103 (0.0047) C34 * 0.0060 (0.0050) C35 * 0.0022 (0.0042) C36

Rms deviation of fitted atoms = 0.0062

1.8669 (0.0145) x - 7.5101 (0.0114) y - 3.4136 (0.0186) z = 0.0000 (0.0000)

Angle to previous plane (with approximate e.s.d.) = 69.46 (0.17)

* 0.0000 (0.0000) N11 * 0.0000 (0.0000) Pd * 0.0000 (0.0000) N31_$1

Rms deviation of fitted atoms = 0.0000

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd	0.000	0.000	0.000	0.03118 (18)
F	−0.0045 (4)	−0.4695 (3)	−0.2670 (3)	0.0730 (9)
O1	0.7974 (5)	0.7313 (5)	0.2395 (4)	0.0874 (14)
O2	0.6004 (6)	0.7853 (5)	0.3236 (4)	0.0850 (14)
N11	0.2269 (4)	0.0717 (4)	−0.0337 (3)	0.0349 (8)
N12	0.2805 (4)	−0.0246 (4)	−0.1213 (3)	0.0366 (8)
N13	0.1707 (4)	−0.1625 (4)	−0.1775 (4)	0.0389 (9)
N31	−0.0860 (4)	0.0475 (4)	−0.1515 (4)	0.0376 (9)
N1	0.6557 (6)	0.6932 (5)	0.2526 (5)	0.0602 (13)
C11	0.3410 (5)	0.2240 (5)	0.0368 (4)	0.0324 (9)
C12	0.5022 (5)	0.2731 (5)	0.0232 (4)	0.0417 (11)
H12	0.5403	0.2024	−0.034	0.05*
C13	0.6041 (5)	0.4257 (6)	0.0946 (5)	0.0468 (12)
H13	0.7113	0.4585	0.0856	0.056*
C14	0.5481 (5)	0.5299 (5)	0.1792 (4)	0.0424 (12)
C15	0.3905 (5)	0.4829 (5)	0.1959 (4)	0.0411 (11)
H15	0.3541	0.5539	0.2547	0.049*
C16	0.2877 (5)	0.3310 (5)	0.1252 (4)	0.0394 (11)
H16	0.1813	0.299	0.1364	0.047*
C21	0.2191 (5)	−0.2668 (5)	−0.2775 (4)	0.0392 (10)
C22	0.1233 (6)	−0.4242 (5)	−0.3235 (5)	0.0460 (11)
C23	0.1531 (7)	−0.5372 (6)	−0.4220 (5)	0.0558 (13)
H23	0.0864	−0.6425	−0.4497	0.067*
C24	0.2826 (7)	−0.4936 (7)	−0.4795 (5)	0.0639 (15)
H24	0.304	−0.5693	−0.5474	0.077*
C25	0.3818 (7)	−0.3368 (7)	−0.4366 (5)	0.0659 (16)
H25	0.4707	−0.3074	−0.475	0.079*
C26	0.3495 (6)	−0.2239 (6)	−0.3369 (5)	0.0552 (13)
H26	0.4156	−0.1184	−0.3095	0.066*
C32	−0.0961 (6)	−0.0402 (6)	−0.2772 (5)	0.0537 (13)
H32	−0.0571	−0.1213	−0.2962	0.064*
C33	−0.1621 (7)	−0.0153 (7)	−0.3802 (6)	0.0714 (17)
H33	−0.1666	−0.0782	−0.4673	0.086*
C34	−0.2202 (8)	0.1002 (10)	−0.3545 (8)	0.092 (2)
H34	−0.268	0.1169	−0.4232	0.11*
C35	−0.2076 (9)	0.1931 (10)	−0.2253 (8)	0.097 (2)
H35	−0.2444	0.2759	−0.205	0.117*
C36	−0.1400 (7)	0.1632 (7)	−0.1252 (6)	0.0684 (17)
H36	−0.1325	0.2261	−0.0374	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd	0.0271 (3)	0.0297 (3)	0.0361 (3)	0.0078 (2)	0.0078 (2)	0.0142 (2)
F	0.073 (2)	0.0492 (17)	0.083 (2)	0.0122 (15)	0.0313 (18)	0.0169 (16)
O1	0.053 (3)	0.075 (3)	0.102 (3)	−0.023 (2)	−0.015 (2)	0.045 (3)
O2	0.102 (4)	0.048 (2)	0.063 (3)	−0.005 (2)	−0.003 (2)	0.006 (2)
N11	0.0295 (19)	0.0360 (19)	0.041 (2)	0.0126 (16)	0.0117 (16)	0.0159 (17)
N12	0.036 (2)	0.043 (2)	0.035 (2)	0.0169 (18)	0.0096 (17)	0.0177 (17)
N13	0.040 (2)	0.039 (2)	0.038 (2)	0.0164 (18)	0.0103 (17)	0.0133 (17)
N31	0.0263 (19)	0.045 (2)	0.049 (2)	0.0129 (17)	0.0095 (17)	0.0266 (19)
N1	0.062 (3)	0.050 (3)	0.049 (3)	−0.009 (2)	−0.019 (2)	0.028 (2)
C11	0.032 (2)	0.036 (2)	0.032 (2)	0.0091 (19)	0.0055 (18)	0.0193 (19)
C12	0.035 (3)	0.050 (3)	0.042 (3)	0.014 (2)	0.008 (2)	0.022 (2)
C13	0.027 (2)	0.064 (3)	0.050 (3)	0.005 (2)	0.002 (2)	0.034 (3)
C14	0.039 (3)	0.038 (2)	0.040 (3)	−0.005 (2)	−0.005 (2)	0.023 (2)
C15	0.046 (3)	0.036 (2)	0.039 (3)	0.012 (2)	0.004 (2)	0.016 (2)
C16	0.032 (2)	0.037 (2)	0.046 (3)	0.005 (2)	0.007 (2)	0.019 (2)
C21	0.042 (3)	0.048 (3)	0.032 (2)	0.021 (2)	0.006 (2)	0.016 (2)
C22	0.049 (3)	0.049 (3)	0.044 (3)	0.022 (2)	0.011 (2)	0.020 (2)
C23	0.069 (4)	0.052 (3)	0.047 (3)	0.033 (3)	0.006 (3)	0.012 (2)
C24	0.081 (4)	0.070 (4)	0.047 (3)	0.049 (3)	0.013 (3)	0.010 (3)
C25	0.065 (4)	0.088 (4)	0.050 (3)	0.037 (3)	0.027 (3)	0.022 (3)
C26	0.056 (3)	0.058 (3)	0.049 (3)	0.020 (3)	0.019 (3)	0.017 (3)
C32	0.056 (3)	0.048 (3)	0.049 (3)	0.014 (2)	−0.006 (3)	0.016 (2)
C33	0.063 (4)	0.079 (4)	0.062 (4)	0.009 (3)	−0.015 (3)	0.036 (3)
C34	0.071 (4)	0.154 (7)	0.096 (6)	0.046 (5)	0.016 (4)	0.098 (6)
C35	0.116 (6)	0.143 (7)	0.123 (6)	0.098 (6)	0.058 (5)	0.103 (6)
C36	0.090 (4)	0.095 (4)	0.074 (4)	0.070 (4)	0.043 (3)	0.059 (4)

Geometric parameters (Å, º)

Pd—N11	2.021 (3)	C15—C16	1.369 (6)
Pd—N11^i	2.021 (3)	C15—H15	0.93
Pd—N31	2.039 (3)	C16—H16	0.93
Pd—N31^i	2.039 (3)	C21—C22	1.378 (6)
Pd—N13	2.903 (4)	C21—C26	1.384 (6)
F—C22	1.353 (5)	C22—C23	1.362 (7)
O1—N1	1.231 (6)	C23—C24	1.366 (7)
O2—N1	1.229 (6)	C23—H23	0.93
N11—N12	1.325 (5)	C24—C25	1.383 (8)
N11—C11	1.403 (5)	C24—H24	0.93
N12—N13	1.283 (5)	C25—C26	1.380 (7)
N13—C21	1.413 (5)	C25—H25	0.93
N31—C36	1.317 (6)	C26—H26	0.93
N31—C32	1.326 (6)	C32—C33	1.370 (7)
N1—C14	1.460 (6)	C32—H32	0.93
C11—C16	1.391 (6)	C33—C34	1.339 (9)
C11—C12	1.397 (6)	C33—H33	0.93
C12—C13	1.373 (6)	C34—C35	1.366 (10)
C12—H12	0.93	C34—H34	0.93
C13—C14	1.371 (7)	C35—C36	1.380 (8)
C13—H13	0.93	C35—H35	0.93
C14—C15	1.377 (6)	C36—H36	0.93
N11—Pd—N11^i	180.0 (2)	C14—C15—H15	120.2
N11—Pd—N31	91.59 (14)	C15—C16—C11	120.6 (4)
N11^i—Pd—N31	88.41 (14)	C15—C16—H16	119.7
N11—Pd—N31^i	88.41 (14)	C11—C16—H16	119.7
N11^i—Pd—N31^i	91.59 (14)	C22—C21—C26	117.5 (4)
N31—Pd—N31^i	180.00 (16)	C22—C21—N13	116.7 (4)
N11—Pd—N13	47.77 (12)	C26—C21—N13	125.8 (4)
N11^i—Pd—N13	132.23 (12)	F—C22—C23	118.2 (4)
N31—Pd—N13	88.44 (12)	F—C22—C21	118.7 (4)
N31^i—Pd—N13	91.56 (12)	C23—C22—C21	123.0 (5)
N12—N11—C11	115.1 (3)	C22—C23—C24	119.0 (5)
N12—N11—Pd	122.0 (3)	C22—C23—H23	120.5
C11—N11—Pd	122.9 (3)	C24—C23—H23	120.5
N13—N12—N11	111.0 (3)	C23—C24—C25	119.9 (5)
N12—N13—C21	113.0 (4)	C23—C24—H24	120
N12—N13—Pd	79.2 (2)	C25—C24—H24	120
C21—N13—Pd	167.3 (3)	C26—C25—C24	120.3 (5)
C36—N31—C32	118.6 (4)	C26—C25—H25	119.9
C36—N31—Pd	119.7 (4)	C24—C25—H25	119.9
C32—N31—Pd	121.6 (3)	C25—C26—C21	120.3 (5)
O2—N1—O1	123.4 (5)	C25—C26—H26	119.8
O2—N1—C14	118.5 (5)	C21—C26—H26	119.8
O1—N1—C14	118.1 (5)	N31—C32—C33	122.3 (5)
C16—C11—C12	119.0 (4)	N31—C32—H32	118.9
C16—C11—N11	116.9 (4)	C33—C32—H32	118.9
C12—C11—N11	124.1 (4)	C34—C33—C32	119.6 (6)
C13—C12—C11	119.9 (4)	C34—C33—H33	120.2
C13—C12—H12	120.1	C32—C33—H33	120.2
C11—C12—H12	120.1	C33—C34—C35	118.6 (6)
C14—C13—C12	120.2 (4)	C33—C34—H34	120.7
C14—C13—H13	119.9	C35—C34—H34	120.7
C12—C13—H13	119.9	C34—C35—C36	119.6 (6)
C13—C14—C15	120.8 (4)	C34—C35—H35	120.2
C13—C14—N1	120.0 (5)	C36—C35—H35	120.2
C15—C14—N1	119.2 (5)	N31—C36—C35	121.3 (6)
C16—C15—C14	119.6 (4)	N31—C36—H36	119.3
C16—C15—H15	120.2	C35—C36—H36	119.3
N31—Pd—N11—N12	−86.4 (3)	O2—N1—C14—C13	177.1 (4)
N31^i—Pd—N11—N12	93.6 (3)	O1—N1—C14—C13	−2.6 (6)
N13—Pd—N11—N12	0.0 (3)	O2—N1—C14—C15	−2.6 (7)
N31—Pd—N11—C11	96.2 (3)	O1—N1—C14—C15	177.7 (4)
N31^i—Pd—N11—C11	−83.8 (3)	C13—C14—C15—C16	−1.2 (7)
N13—Pd—N11—C11	−177.3 (4)	N1—C14—C15—C16	178.5 (4)
C11—N11—N12—N13	177.5 (3)	C14—C15—C16—C11	−0.1 (7)
Pd—N11—N12—N13	0.0 (5)	C12—C11—C16—C15	1.4 (6)
N11—N12—N13—C21	176.3 (3)	N11—C11—C16—C15	−178.6 (4)
N11—N12—N13—Pd	0.0 (3)	N12—N13—C21—C22	166.9 (4)
N11—Pd—N13—N12	0.0 (2)	Pd—N13—C21—C22	−29.7 (15)
N11^i—Pd—N13—N12	180.0 (2)	N12—N13—C21—C26	−16.1 (6)
N31—Pd—N13—N12	93.6 (2)	Pd—N13—C21—C26	147.3 (11)
N31^i—Pd—N13—N12	−86.4 (2)	C26—C21—C22—F	179.7 (4)
N11—Pd—N13—C21	−164.5 (13)	N13—C21—C22—F	−3.0 (6)
N11^i—Pd—N13—C21	15.5 (13)	C26—C21—C22—C23	1.0 (7)
N31—Pd—N13—C21	−70.9 (13)	N13—C21—C22—C23	178.3 (4)
N31^i—Pd—N13—C21	109.1 (13)	F—C22—C23—C24	−179.4 (5)
N11—Pd—N31—C36	−112.1 (4)	C21—C22—C23—C24	−0.7 (8)
N11^i—Pd—N31—C36	67.9 (4)	C22—C23—C24—C25	0.6 (8)
N13—Pd—N31—C36	−159.8 (4)	C23—C24—C25—C26	−0.8 (8)
N11—Pd—N31—C32	71.1 (4)	C24—C25—C26—C21	1.1 (8)
N11^i—Pd—N31—C32	−108.9 (4)	C22—C21—C26—C25	−1.2 (7)
N13—Pd—N31—C32	23.4 (3)	N13—C21—C26—C25	−178.1 (5)
N12—N11—C11—C16	177.1 (3)	C36—N31—C32—C33	−0.6 (7)
Pd—N11—C11—C16	−5.4 (5)	Pd—N31—C32—C33	176.2 (4)
N12—N11—C11—C12	−2.9 (6)	N31—C32—C33—C34	−0.6 (9)
Pd—N11—C11—C12	174.6 (3)	C32—C33—C34—C35	1.8 (10)
C16—C11—C12—C13	−1.4 (6)	C33—C34—C35—C36	−1.8 (11)
N11—C11—C12—C13	178.6 (4)	C32—N31—C36—C35	0.7 (8)
C11—C12—C13—C14	0.1 (7)	Pd—N31—C36—C35	−176.2 (5)
C12—C13—C14—C15	1.2 (7)	C34—C35—C36—N31	0.5 (10)
C12—C13—C14—N1	−178.5 (4)

Symmetry code: (i) −x, −y, −z.