Tetra-kis(4-cyano-pyridine)-palladium(II) bis-(trifluoro-methane-sulfonate).

The title salt, [Pd(C(6)H(4)N(2))(4)](CF(3)SO(3))(2), comprises Pd(4-cyano-pyridine)(4) dications balanced by two trifluoro-methane-sulfonate anions. The Pd(II) atom lies in a square-planar geometry defined by four N atoms which form equivalent Pd-N inter-actions. The 4-cyano-pyridine ligands are twisted out of the N(4) plane, forming dihedral angles ranging from 66.5 (2) to 89.9 (2)°. In the crystal packing, columns of edge-to-edge dications define channels in which reside the anions. A range of C-H⋯N and C-H⋯O hydrogen-bonding interactions stabilizes the crystal packing.

Related literature

For related palladium(II) complexes with 4-cyano­pyridine, see: Kopylovich et al. (2009 ▶); Lang et al. (2006 ▶); Taher et al. (2006 ▶).

Experimental

Crystal data

[Pd(C6H4N2)4](CF3O3S)2

M = 820.99

Monoclinic,

a = 18.550 (4) Å

b = 9.2993 (19) Å

c = 20.688 (4) Å

β = 114.55 (3)°

V = 3246.1 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 153 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.829, T max = 1.000

12799 measured reflections

5478 independent reflections

5000 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.14

5478 reflections

442 parameters

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.74 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027704/ez2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027704/ez2223Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pd(C6H4N2)4](CF3O3S)2	F(000) = 1632
Mr = 820.99	Dx = 1.680 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4545 reflections
a = 18.550 (4) Å	θ = 2.4–26.7°
b = 9.2993 (19) Å	µ = 0.79 mm−1
c = 20.688 (4) Å	T = 153 K
β = 114.55 (3)°	Block, pale-yellow
V = 3246.1 (14) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku AFC12K/SATURN724 diffractometer	5478 independent reflections
Radiation source: fine-focus sealed tube	5000 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→20
Tmin = 0.829, Tmax = 1.000	k = −9→11
12799 measured reflections	l = −24→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0534P)2 + 6.3187P] where P = (Fo2 + 2Fc2)/3
5478 reflections	(Δ/σ)max = 0.001
442 parameters	Δρmax = 1.05 e Å−3
0 restraints	Δρmin = −0.74 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Pd	0.254695 (18)	0.02757 (4)	0.766848 (17)	0.02851 (14)
S1	0.39867 (7)	0.39076 (14)	0.77597 (7)	0.0421 (3)
S2	0.11861 (7)	0.66442 (14)	0.77812 (7)	0.0384 (3)
F1	0.3763 (3)	0.3677 (5)	0.6440 (2)	0.0951 (14)
F2	0.4595 (3)	0.5294 (4)	0.7007 (3)	0.0944 (14)
F3	0.4938 (3)	0.3095 (5)	0.7191 (2)	0.0874 (13)
F4	−0.03138 (19)	0.7372 (4)	0.7237 (2)	0.0733 (10)
F5	−0.0103 (2)	0.5195 (4)	0.7061 (3)	0.0954 (15)
F6	0.0144 (2)	0.6830 (5)	0.64715 (19)	0.0856 (12)
O1	0.3355 (2)	0.4938 (4)	0.7542 (2)	0.0559 (10)
O2	0.3714 (2)	0.2450 (4)	0.7711 (2)	0.0571 (10)
O3	0.4674 (2)	0.4248 (5)	0.8390 (2)	0.0701 (13)
O4	0.1119 (2)	0.6364 (5)	0.8435 (2)	0.0661 (12)
O5	0.1394 (2)	0.8100 (4)	0.7697 (2)	0.0499 (9)
O6	0.1616 (2)	0.5589 (4)	0.7574 (2)	0.0545 (10)
N1	0.3470 (2)	−0.0809 (4)	0.84066 (18)	0.0300 (8)
N2	0.5954 (3)	−0.3914 (7)	1.0098 (3)	0.0771 (17)
N3	0.2329 (2)	0.1341 (4)	0.84253 (19)	0.0306 (8)
N4	0.1540 (3)	0.4235 (6)	1.0271 (3)	0.0672 (14)
N5	0.1614 (2)	0.1304 (4)	0.69095 (19)	0.0316 (8)
N6	−0.0892 (3)	0.4022 (6)	0.4987 (3)	0.0653 (14)
N7	0.2771 (2)	−0.0774 (4)	0.69126 (19)	0.0318 (8)
N8	0.3503 (3)	−0.3732 (6)	0.5062 (2)	0.0570 (12)
C1	0.3401 (3)	−0.2230 (5)	0.8488 (2)	0.0354 (10)
H1	0.2905	−0.2682	0.8230	0.042*
C2	0.4029 (3)	−0.3051 (5)	0.8936 (2)	0.0392 (11)
H2	0.3966	−0.4052	0.8988	0.047*
C3	0.4752 (3)	−0.2391 (6)	0.9307 (2)	0.0380 (11)
C4	0.4820 (3)	−0.0920 (6)	0.9233 (2)	0.0405 (11)
H4	0.5310	−0.0444	0.9490	0.049*
C5	0.4169 (3)	−0.0165 (5)	0.8782 (2)	0.0349 (10)
H5	0.4215	0.0843	0.8735	0.042*
C6	0.5424 (3)	−0.3230 (6)	0.9757 (3)	0.0501 (13)
C7	0.2062 (3)	0.0623 (6)	0.8847 (2)	0.0399 (11)
H7	0.2007	−0.0392	0.8804	0.048*
C8	0.1865 (3)	0.1317 (6)	0.9340 (3)	0.0437 (12)
H8	0.1679	0.0793	0.9634	0.052*
C9	0.1945 (3)	0.2796 (5)	0.9396 (2)	0.0360 (11)
C10	0.2225 (3)	0.3537 (5)	0.8974 (2)	0.0374 (11)
H10	0.2288	0.4552	0.9011	0.045*
C11	0.2414 (3)	0.2758 (5)	0.8491 (2)	0.0364 (11)
H11	0.2610	0.3258	0.8197	0.044*
C12	0.1719 (3)	0.3602 (6)	0.9892 (3)	0.0493 (13)
C13	0.0912 (3)	0.0632 (6)	0.6598 (3)	0.0390 (11)
H13	0.0869	−0.0332	0.6731	0.047*
C14	0.0258 (3)	0.1282 (6)	0.6098 (3)	0.0419 (12)
H14	−0.0230	0.0779	0.5882	0.050*
C15	0.0324 (3)	0.2699 (6)	0.5912 (2)	0.0424 (12)
C16	0.1042 (3)	0.3394 (6)	0.6227 (3)	0.0460 (12)
H16	0.1096	0.4360	0.6105	0.055*
C17	0.1682 (3)	0.2669 (5)	0.6723 (2)	0.0406 (11)
H17	0.2179	0.3142	0.6938	0.049*
C18	−0.0355 (3)	0.3426 (6)	0.5394 (3)	0.0514 (14)
C19	0.2442 (3)	−0.2063 (5)	0.6675 (2)	0.0383 (11)
H19	0.2079	−0.2450	0.6845	0.046*
C20	0.2615 (3)	−0.2836 (6)	0.6192 (3)	0.0425 (12)
H20	0.2377	−0.3746	0.6028	0.051*
C21	0.3145 (3)	−0.2260 (5)	0.5948 (2)	0.0370 (11)
C22	0.3479 (3)	−0.0935 (6)	0.6189 (3)	0.0453 (12)
H22	0.3839	−0.0519	0.6024	0.054*
C23	0.3278 (3)	−0.0227 (6)	0.6675 (3)	0.0426 (12)
H23	0.3509	0.0684	0.6847	0.051*
C24	0.3344 (3)	−0.3078 (6)	0.5450 (3)	0.0462 (13)
C25	0.4345 (4)	0.4002 (7)	0.7071 (4)	0.0596 (16)
C26	0.0176 (3)	0.6496 (6)	0.7111 (3)	0.0548 (14)

	U11	U22	U33	U12	U13	U23
Pd	0.0277 (2)	0.0264 (2)	0.0324 (2)	0.00416 (13)	0.01340 (16)	0.00318 (13)
S1	0.0410 (7)	0.0374 (7)	0.0541 (7)	−0.0029 (6)	0.0259 (6)	−0.0035 (6)
S2	0.0339 (6)	0.0349 (7)	0.0495 (7)	0.0020 (5)	0.0202 (5)	0.0073 (5)
F1	0.120 (4)	0.117 (4)	0.054 (2)	−0.012 (3)	0.042 (2)	−0.002 (2)
F2	0.125 (4)	0.060 (3)	0.141 (4)	−0.020 (2)	0.098 (3)	0.008 (2)
F3	0.105 (3)	0.089 (3)	0.106 (3)	0.034 (3)	0.081 (3)	0.019 (2)
F4	0.0419 (18)	0.072 (3)	0.097 (3)	0.0145 (18)	0.0206 (18)	−0.004 (2)
F5	0.059 (2)	0.055 (2)	0.155 (4)	−0.0209 (19)	0.027 (3)	−0.007 (2)
F6	0.069 (2)	0.119 (4)	0.053 (2)	−0.011 (2)	0.0098 (18)	−0.002 (2)
O1	0.051 (2)	0.045 (2)	0.075 (3)	0.0109 (18)	0.029 (2)	−0.0001 (19)
O2	0.072 (3)	0.038 (2)	0.078 (3)	−0.0120 (19)	0.048 (2)	0.0012 (19)
O3	0.045 (2)	0.097 (4)	0.063 (3)	−0.002 (2)	0.017 (2)	−0.026 (3)
O4	0.060 (2)	0.092 (3)	0.060 (2)	0.019 (2)	0.038 (2)	0.026 (2)
O5	0.041 (2)	0.038 (2)	0.066 (2)	−0.0062 (16)	0.0177 (18)	0.0011 (17)
O6	0.048 (2)	0.048 (2)	0.074 (3)	0.0121 (18)	0.032 (2)	0.002 (2)
N1	0.0284 (19)	0.031 (2)	0.0310 (19)	0.0028 (16)	0.0124 (16)	−0.0009 (16)
N2	0.047 (3)	0.080 (4)	0.086 (4)	0.017 (3)	0.009 (3)	0.031 (3)
N3	0.0274 (18)	0.029 (2)	0.0354 (19)	0.0015 (16)	0.0130 (16)	0.0055 (16)
N4	0.080 (4)	0.079 (4)	0.057 (3)	0.001 (3)	0.042 (3)	−0.014 (3)
N5	0.032 (2)	0.029 (2)	0.0340 (19)	0.0043 (16)	0.0146 (16)	0.0028 (16)
N6	0.058 (3)	0.064 (3)	0.058 (3)	0.018 (3)	0.007 (3)	0.010 (3)
N7	0.0269 (19)	0.033 (2)	0.0353 (19)	0.0051 (16)	0.0123 (16)	0.0062 (17)
N8	0.063 (3)	0.065 (3)	0.049 (3)	0.010 (3)	0.030 (2)	−0.005 (2)
C1	0.032 (2)	0.031 (3)	0.041 (2)	−0.001 (2)	0.013 (2)	−0.002 (2)
C2	0.043 (3)	0.031 (3)	0.039 (3)	0.007 (2)	0.013 (2)	0.002 (2)
C3	0.035 (3)	0.045 (3)	0.032 (2)	0.011 (2)	0.012 (2)	0.005 (2)
C4	0.030 (2)	0.051 (3)	0.038 (3)	−0.003 (2)	0.011 (2)	0.000 (2)
C5	0.039 (3)	0.032 (3)	0.036 (2)	−0.001 (2)	0.018 (2)	0.002 (2)
C6	0.037 (3)	0.055 (4)	0.051 (3)	0.008 (3)	0.011 (2)	0.009 (3)
C7	0.043 (3)	0.038 (3)	0.040 (3)	−0.001 (2)	0.019 (2)	0.004 (2)
C8	0.049 (3)	0.048 (3)	0.040 (3)	−0.005 (2)	0.025 (2)	0.000 (2)
C9	0.032 (2)	0.046 (3)	0.029 (2)	0.004 (2)	0.0117 (19)	0.000 (2)
C10	0.040 (3)	0.033 (3)	0.038 (2)	0.006 (2)	0.016 (2)	−0.001 (2)
C11	0.041 (3)	0.032 (3)	0.041 (3)	0.001 (2)	0.021 (2)	0.006 (2)
C12	0.052 (3)	0.057 (4)	0.043 (3)	0.001 (3)	0.024 (3)	−0.003 (3)
C13	0.039 (3)	0.038 (3)	0.043 (3)	0.005 (2)	0.019 (2)	0.008 (2)
C14	0.035 (3)	0.048 (3)	0.043 (3)	0.003 (2)	0.016 (2)	0.005 (2)
C15	0.044 (3)	0.047 (3)	0.036 (2)	0.017 (2)	0.017 (2)	0.003 (2)
C16	0.053 (3)	0.031 (3)	0.044 (3)	0.005 (2)	0.009 (2)	0.006 (2)
C17	0.042 (3)	0.034 (3)	0.039 (3)	0.003 (2)	0.009 (2)	0.001 (2)
C18	0.051 (3)	0.049 (3)	0.046 (3)	0.015 (3)	0.011 (3)	0.002 (3)
C19	0.043 (3)	0.038 (3)	0.042 (3)	−0.007 (2)	0.026 (2)	−0.007 (2)
C20	0.048 (3)	0.036 (3)	0.046 (3)	−0.009 (2)	0.022 (2)	−0.007 (2)
C21	0.036 (2)	0.040 (3)	0.034 (2)	0.010 (2)	0.014 (2)	0.003 (2)
C22	0.048 (3)	0.044 (3)	0.055 (3)	−0.005 (2)	0.032 (3)	−0.002 (2)
C23	0.046 (3)	0.036 (3)	0.055 (3)	−0.007 (2)	0.030 (3)	−0.005 (2)
C24	0.049 (3)	0.052 (3)	0.041 (3)	0.008 (3)	0.022 (2)	0.001 (2)
C25	0.076 (4)	0.044 (4)	0.077 (4)	−0.003 (3)	0.050 (4)	0.002 (3)
C26	0.047 (3)	0.044 (3)	0.073 (4)	−0.007 (3)	0.024 (3)	−0.002 (3)

Pd—N1	2.027 (4)	C2—H2	0.9500
Pd—N3	2.031 (4)	C3—C4	1.388 (7)
Pd—N5	2.029 (4)	C3—C6	1.437 (7)
Pd—N7	2.027 (4)	C4—C5	1.373 (7)
S1—O3	1.430 (4)	C4—H4	0.9500
S1—O1	1.434 (4)	C5—H5	0.9500
S1—O2	1.435 (4)	C7—C8	1.377 (7)
S1—C25	1.808 (6)	C7—H7	0.9500
S2—O4	1.433 (4)	C8—C9	1.383 (7)
S2—O5	1.438 (4)	C8—H8	0.9500
S2—O6	1.439 (4)	C9—C10	1.372 (7)
S2—C26	1.815 (6)	C9—C12	1.465 (7)
F1—C25	1.338 (8)	C10—C11	1.392 (6)
F2—C25	1.313 (7)	C10—H10	0.9500
F3—C25	1.325 (7)	C11—H11	0.9500
F4—C26	1.325 (7)	C13—C14	1.366 (7)
F5—C26	1.304 (7)	C13—H13	0.9500
F6—C26	1.335 (7)	C14—C15	1.393 (7)
N1—C5	1.344 (6)	C14—H14	0.9500
N1—C1	1.345 (6)	C15—C16	1.377 (7)
N2—C6	1.137 (7)	C15—C18	1.439 (7)
N3—C11	1.327 (6)	C16—C17	1.379 (7)
N3—C7	1.346 (6)	C16—H16	0.9500
N4—C12	1.135 (7)	C17—H17	0.9500
N5—C13	1.343 (6)	C19—C20	1.373 (7)
N5—C17	1.347 (6)	C19—H19	0.9500
N6—C18	1.146 (7)	C20—C21	1.385 (7)
N7—C23	1.330 (6)	C20—H20	0.9500
N7—C19	1.342 (6)	C21—C22	1.376 (7)
N8—C24	1.140 (6)	C21—C24	1.447 (7)
C1—C2	1.379 (6)	C22—C23	1.377 (7)
C1—H1	0.9500	C22—H22	0.9500
C2—C3	1.380 (7)	C23—H23	0.9500
N1—Pd—N7	87.80 (14)	C10—C9—C12	118.8 (5)
N1—Pd—N5	178.15 (15)	C8—C9—C12	121.1 (4)
N7—Pd—N5	90.70 (14)	C9—C10—C11	118.0 (5)
N1—Pd—N3	92.21 (14)	C9—C10—H10	121.0
N7—Pd—N3	179.53 (15)	C11—C10—H10	121.0
N5—Pd—N3	89.29 (14)	N3—C11—C10	122.4 (4)
O3—S1—O1	116.1 (3)	N3—C11—H11	118.8
O3—S1—O2	115.4 (3)	C10—C11—H11	118.8
O1—S1—O2	113.0 (2)	N4—C12—C9	179.4 (7)
O3—S1—C25	103.2 (3)	N5—C13—C14	122.4 (5)
O1—S1—C25	103.9 (3)	N5—C13—H13	118.8
O2—S1—C25	102.9 (3)	C14—C13—H13	118.8
O4—S2—O5	114.7 (3)	C13—C14—C15	118.5 (5)
O4—S2—O6	115.7 (3)	C13—C14—H14	120.8
O5—S2—O6	113.4 (2)	C15—C14—H14	120.8
O4—S2—C26	103.9 (3)	C16—C15—C14	119.4 (5)
O5—S2—C26	102.8 (2)	C16—C15—C18	120.5 (5)
O6—S2—C26	104.2 (3)	C14—C15—C18	120.1 (5)
C5—N1—C1	119.0 (4)	C15—C16—C17	119.2 (5)
C5—N1—Pd	121.6 (3)	C15—C16—H16	120.4
C1—N1—Pd	119.3 (3)	C17—C16—H16	120.4
C11—N3—C7	119.1 (4)	N5—C17—C16	121.3 (5)
C11—N3—Pd	120.7 (3)	N5—C17—H17	119.4
C7—N3—Pd	120.2 (3)	C16—C17—H17	119.4
C13—N5—C17	119.2 (4)	N6—C18—C15	179.0 (6)
C13—N5—Pd	119.8 (3)	N7—C19—C20	121.7 (4)
C17—N5—Pd	121.0 (3)	N7—C19—H19	119.1
C23—N7—C19	119.3 (4)	C20—C19—H19	119.1
C23—N7—Pd	120.2 (3)	C19—C20—C21	118.6 (5)
C19—N7—Pd	120.4 (3)	C19—C20—H20	120.7
N1—C1—C2	122.0 (4)	C21—C20—H20	120.7
N1—C1—H1	119.0	C22—C21—C20	119.7 (4)
C2—C1—H1	119.0	C22—C21—C24	121.3 (5)
C1—C2—C3	118.8 (5)	C20—C21—C24	119.1 (5)
C1—C2—H2	120.6	C21—C22—C23	118.3 (5)
C3—C2—H2	120.6	C21—C22—H22	120.8
C2—C3—C4	119.2 (4)	C23—C22—H22	120.8
C2—C3—C6	120.0 (5)	N7—C23—C22	122.3 (5)
C4—C3—C6	120.8 (5)	N7—C23—H23	118.8
C5—C4—C3	119.0 (5)	C22—C23—H23	118.8
C5—C4—H4	120.5	N8—C24—C21	179.4 (6)
C3—C4—H4	120.5	F2—C25—F3	107.5 (5)
N1—C5—C4	122.0 (5)	F2—C25—F1	106.5 (6)
N1—C5—H5	119.0	F3—C25—F1	108.1 (5)
C4—C5—H5	119.0	F2—C25—S1	112.5 (4)
N2—C6—C3	178.1 (7)	F3—C25—S1	111.7 (4)
N3—C7—C8	121.9 (5)	F1—C25—S1	110.2 (4)
N3—C7—H7	119.0	F5—C26—F4	107.6 (5)
C8—C7—H7	119.0	F5—C26—F6	106.6 (5)
C7—C8—C9	118.5 (5)	F4—C26—F6	107.5 (5)
C7—C8—H8	120.8	F5—C26—S2	112.4 (4)
C9—C8—H8	120.8	F4—C26—S2	112.2 (4)
C10—C9—C8	120.1 (4)	F6—C26—S2	110.3 (4)
N7—Pd—N1—C5	105.2 (3)	Pd—N5—C13—C14	178.3 (4)
N3—Pd—N1—C5	−74.3 (3)	N5—C13—C14—C15	−0.7 (7)
N7—Pd—N1—C1	−70.1 (3)	C13—C14—C15—C16	0.9 (7)
N3—Pd—N1—C1	110.4 (3)	C13—C14—C15—C18	−179.2 (5)
N1—Pd—N3—C11	115.5 (4)	C14—C15—C16—C17	−0.2 (7)
N5—Pd—N3—C11	−65.6 (4)	C18—C15—C16—C17	179.9 (5)
N1—Pd—N3—C7	−67.5 (3)	C13—N5—C17—C16	0.9 (7)
N5—Pd—N3—C7	111.5 (3)	Pd—N5—C17—C16	−177.5 (4)
N7—Pd—N5—C13	81.3 (3)	C15—C16—C17—N5	−0.7 (8)
N3—Pd—N5—C13	−99.2 (3)	C23—N7—C19—C20	0.1 (7)
N7—Pd—N5—C17	−100.3 (4)	Pd—N7—C19—C20	−176.4 (4)
N3—Pd—N5—C17	79.2 (4)	N7—C19—C20—C21	0.0 (7)
N1—Pd—N7—C23	−88.8 (4)	C19—C20—C21—C22	−0.4 (7)
N5—Pd—N7—C23	92.3 (4)	C19—C20—C21—C24	178.8 (5)
N1—Pd—N7—C19	87.7 (4)	C20—C21—C22—C23	0.7 (7)
N5—Pd—N7—C19	−91.3 (4)	C24—C21—C22—C23	−178.5 (5)
C5—N1—C1—C2	−1.2 (7)	C19—N7—C23—C22	0.2 (7)
Pd—N1—C1—C2	174.3 (3)	Pd—N7—C23—C22	176.7 (4)
N1—C1—C2—C3	−0.5 (7)	C21—C22—C23—N7	−0.6 (8)
C1—C2—C3—C4	1.6 (7)	O3—S1—C25—F2	−62.4 (6)
C1—C2—C3—C6	−177.7 (5)	O1—S1—C25—F2	59.2 (6)
C2—C3—C4—C5	−1.1 (7)	O2—S1—C25—F2	177.3 (5)
C6—C3—C4—C5	178.2 (4)	O3—S1—C25—F3	58.7 (5)
C1—N1—C5—C4	1.7 (7)	O1—S1—C25—F3	−179.7 (4)
Pd—N1—C5—C4	−173.6 (3)	O2—S1—C25—F3	−61.6 (5)
C3—C4—C5—N1	−0.6 (7)	O3—S1—C25—F1	178.8 (4)
C11—N3—C7—C8	0.7 (7)	O1—S1—C25—F1	−59.5 (5)
Pd—N3—C7—C8	−176.3 (4)	O2—S1—C25—F1	58.5 (5)
N3—C7—C8—C9	0.2 (7)	O4—S2—C26—F5	−65.3 (5)
C7—C8—C9—C10	−0.9 (7)	O5—S2—C26—F5	174.8 (5)
C7—C8—C9—C12	177.8 (5)	O6—S2—C26—F5	56.3 (5)
C8—C9—C10—C11	0.6 (7)	O4—S2—C26—F4	56.1 (5)
C12—C9—C10—C11	−178.0 (4)	O5—S2—C26—F4	−63.8 (5)
C7—N3—C11—C10	−1.0 (7)	O6—S2—C26—F4	177.7 (4)
Pd—N3—C11—C10	176.1 (3)	O4—S2—C26—F6	175.9 (4)
C9—C10—C11—N3	0.3 (7)	O5—S2—C26—F6	56.0 (5)
C17—N5—C13—C14	−0.2 (7)	O6—S2—C26—F6	−62.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N8i	0.95	2.56	3.489 (8)	166
C5—H5···O2	0.95	2.44	3.159 (6)	132
C7—H7···O5ii	0.95	2.52	3.202 (6)	129
C8—H8···N6iii	0.95	2.53	3.441 (8)	160
C13—H13···O5ii	0.95	2.33	3.134 (7)	141
C16—H16···N6iv	0.95	2.61	3.403 (8)	142
C22—H22···O3v	0.95	2.52	3.170 (7)	126
C23—H23···O2	0.95	2.34	3.163 (7)	145

Table 1

Selected bond lengths (Å)

Pd—N1	2.027 (4)
Pd—N3	2.031 (4)
Pd—N5	2.029 (4)
Pd—N7	2.027 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N8i	0.95	2.56	3.489 (8)	166
C5—H5⋯O2	0.95	2.44	3.159 (6)	132
C7—H7⋯O5ii	0.95	2.52	3.202 (6)	129
C8—H8⋯N6iii	0.95	2.53	3.441 (8)	160
C13—H13⋯O5ii	0.95	2.33	3.134 (7)	141
C16—H16⋯N6iv	0.95	2.61	3.403 (8)	142
C22—H22⋯O3v	0.95	2.52	3.170 (7)	126
C23—H23⋯O2	0.95	2.34	3.163 (7)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .