Side-chain conformations in the isomorphous polyfluorinated {4,4′-bis[(2,2-di­fluoro­eth­oxy)meth­yl]-2,2′-bi­pyridine-κ²N,N′}di­chlorido­palladium and -platinum complexes

The polyfluorinated title compounds, [MCl₂(C₁₆H₁₆F₄N₂O₂)] or [4,4′-(HCF₂CH₂OCH₂)₂-2,2′-bpy]MCl₂ [M = Pd, (1), and M = Pt, (2)], have –C(H_α)₂OC(H_β)₂CF₂H side chains with H-atom donors at the α and β sites. The structures of (1) and (2) are isomorphous, with the nearly planar (bpy)MCl₂ molecules stacked in columns. Within one column, π-dimer pairs alternate between a π-dimer pair reinforced with C—H...Cl hydrogen bonds (α,α) and a π-dimer pair reinforced with C—H_β...F(—C) inter­actions (abbreviated as C—H_β...F—C,C—H_β...F—C). The compounds [4,4′-(CF₃CH₂OCH₂)₂-2,2′-bpy]MCl₂ [M = Pd, (3), and M = Pt, (4)] have been reported to be isomorphous [Lu et al. (2012). J. Fluorine Chem. 137, 54–56], yet with disorder in the fluorous regions. The mol­ecules of (3) [or (4)] also form similar stacks, but with alternating π-dimer pairs between the (α,β; α,β) and (β,β) forms. Through (C—)H...Cl hydrogen-bond inter­actions, one mol­ecule of (1) [or (2)] is expanded into an aggregate of two inversion-related π-dimer pairs, one pair in the (α,α) form and the other pair in the (C—H_β...F—C,C—H_β...F—C) form, with the plane normals making an interplanar angle of 58.24 (3)°. Due to the demands of maintaining a high coordination number around the metal-bound Cl atoms in mol­ecule (1) [or (2)], the ponytails of mol­ecule (1) [or (2)] bend outward; in contrast, the ponytails of mol­ecule (3) [or (4)] bend inward.

Computing details

For both structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle et al., 2011); software used to prepare material for publication: WinGX (Farrugia, 2012).

{4,4'-Bis[(2,2-difluoroethoxy)methyl]-2,2'-bipyridine-κ²N,N'}dichloridopalladium and -platinum (i12726)

Crystal data

[PdCl2(C16H16F4N2O2)]	Dx = 1.916 Mg m^−3
Mr = 521.61	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9893 reflections
a = 7.7401 (2) Å	θ = 2.6–32.1°
b = 16.5086 (4) Å	µ = 1.38 mm^−1
c = 28.3013 (7) Å	T = 295 K
V = 3616.29 (16) Å^3	Prism, orange
Z = 8	0.24 × 0.22 × 0.18 mm
F(000) = 2064

Data collection

Bruker APEXII CCD diffractometer	3173 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.054
Absorption correction: multi-scan (SADABS; Bruker, 1996)	θmax = 26.4°, θmin = 2.5°
Tmin = 0.809, Tmax = 0.971	h = −9→9
59415 measured reflections	k = −20→18
3702 independent reflections	l = −35→35

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.051	w = 1/[σ^2(Fo^2) + (0.0151P)^2 + 5.2894P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.003
3702 reflections	Δρmax = 0.43 e Å^−3
252 parameters	Δρmin = −0.65 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.

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

	x	y	z	Uiso*/Ueq
Pd	0.42460 (2)	0.85543 (2)	0.54593 (2)	0.01366 (6)
Cl1	0.46751 (7)	0.74610 (3)	0.49780 (2)	0.01877 (12)
Cl2	0.56776 (8)	0.79099 (3)	0.60642 (2)	0.01849 (12)
F1	0.3347 (2)	1.14754 (9)	0.76921 (6)	0.0320 (4)
F2	0.3056 (2)	1.27837 (9)	0.76749 (6)	0.0345 (4)
F3	−0.1033 (2)	0.98226 (10)	0.26759 (6)	0.0411 (4)
O1	0.3825 (2)	1.21584 (10)	0.68130 (6)	0.0191 (4)
O2	0.0185 (3)	1.03653 (10)	0.35459 (6)	0.0279 (4)
N1	0.3954 (2)	0.96204 (11)	0.58108 (7)	0.0150 (4)
N2	0.2923 (2)	0.91795 (11)	0.49658 (7)	0.0148 (4)
C1	0.3267 (3)	1.02234 (13)	0.55416 (8)	0.0151 (5)
C2	0.3170 (3)	1.10138 (13)	0.57079 (8)	0.0153 (5)
H2	0.2695	1.1419	0.5520	0.018*
C3	0.3786 (3)	1.11956 (14)	0.61556 (8)	0.0167 (5)
C4	0.4421 (3)	1.05677 (14)	0.64325 (9)	0.0194 (5)
H4	0.4796	1.0668	0.6739	0.023*
F4	0.0223 (3)	1.08427 (10)	0.23322 (6)	0.0496 (5)
C5	0.4493 (3)	0.97926 (14)	0.62490 (8)	0.0185 (5)
H5	0.4931	0.9377	0.6436	0.022*
C6	0.2658 (3)	0.99752 (13)	0.50719 (8)	0.0137 (4)
C7	0.1869 (3)	1.04930 (13)	0.47545 (8)	0.0150 (5)
H7	0.1718	1.1036	0.4831	0.018*
C8	0.1301 (3)	1.01992 (13)	0.43203 (8)	0.0146 (5)
C9	0.1518 (3)	0.93813 (14)	0.42258 (8)	0.0173 (5)
H9	0.1114	0.9163	0.3944	0.021*
C10	0.2337 (3)	0.88910 (14)	0.45522 (8)	0.0166 (5)
H10	0.2488	0.8345	0.4483	0.020*
C11	0.3848 (3)	1.20713 (14)	0.63135 (8)	0.0196 (5)
H11A	0.4888	1.2321	0.6190	0.023*
H11B	0.2865	1.2357	0.6181	0.023*
C12	0.2140 (3)	1.20527 (16)	0.70064 (9)	0.0219 (5)
H12A	0.1665	1.1536	0.6907	0.026*
H12B	0.1379	1.2480	0.6896	0.026*
C13	0.2277 (3)	1.20801 (16)	0.75317 (10)	0.0242 (5)
C14	0.0510 (3)	1.07784 (14)	0.39745 (8)	0.0187 (5)
H14A	−0.0561	1.0992	0.4101	0.022*
H14B	0.1290	1.1228	0.3919	0.022*
C15	−0.0052 (4)	1.08781 (15)	0.31527 (9)	0.0292 (6)
H15A	0.0758	1.1326	0.3164	0.035*
H15B	−0.1217	1.1095	0.3150	0.035*
C16	0.0252 (4)	1.03779 (16)	0.27273 (10)	0.0304 (6)
H13	0.113 (3)	1.2038 (15)	0.7697 (9)	0.019 (7)*
H16	0.147 (4)	1.0054 (17)	0.2750 (10)	0.030 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd	0.01440 (9)	0.01048 (9)	0.01611 (9)	−0.00037 (7)	0.00104 (7)	0.00137 (7)
Cl1	0.0206 (3)	0.0115 (2)	0.0242 (3)	0.0008 (2)	−0.0018 (2)	−0.0021 (2)
Cl2	0.0211 (3)	0.0155 (3)	0.0189 (3)	0.0016 (2)	−0.0016 (2)	0.0038 (2)
F1	0.0312 (9)	0.0347 (9)	0.0301 (8)	0.0025 (7)	−0.0041 (7)	0.0072 (7)
F2	0.0437 (10)	0.0314 (8)	0.0285 (9)	0.0005 (7)	0.0006 (7)	−0.0122 (7)
F3	0.0461 (11)	0.0347 (9)	0.0424 (10)	−0.0044 (8)	−0.0147 (8)	−0.0086 (8)
O1	0.0188 (9)	0.0227 (9)	0.0158 (8)	−0.0007 (7)	−0.0003 (7)	−0.0041 (7)
O2	0.0494 (12)	0.0169 (8)	0.0174 (9)	−0.0048 (8)	−0.0101 (8)	0.0028 (7)
N1	0.0161 (10)	0.0136 (9)	0.0152 (10)	−0.0009 (8)	0.0021 (8)	0.0018 (8)
N2	0.0150 (9)	0.0119 (9)	0.0176 (10)	−0.0018 (7)	0.0026 (8)	−0.0003 (8)
C1	0.0125 (11)	0.0148 (11)	0.0181 (12)	−0.0008 (9)	0.0018 (9)	0.0025 (9)
C2	0.0151 (11)	0.0146 (11)	0.0162 (12)	0.0002 (9)	0.0023 (9)	0.0024 (9)
C3	0.0167 (12)	0.0165 (11)	0.0170 (12)	−0.0016 (9)	0.0035 (9)	−0.0020 (9)
C4	0.0211 (12)	0.0208 (12)	0.0162 (12)	−0.0002 (10)	0.0001 (10)	−0.0016 (10)
F4	0.0931 (16)	0.0382 (10)	0.0176 (8)	0.0061 (10)	0.0008 (9)	0.0021 (7)
C5	0.0200 (12)	0.0195 (12)	0.0161 (12)	0.0023 (10)	−0.0006 (10)	0.0010 (9)
C6	0.0107 (10)	0.0133 (10)	0.0172 (12)	−0.0018 (9)	0.0040 (9)	0.0001 (9)
C7	0.0140 (11)	0.0117 (10)	0.0191 (12)	−0.0016 (8)	0.0026 (9)	−0.0002 (9)
C8	0.0114 (11)	0.0157 (11)	0.0167 (12)	−0.0013 (9)	0.0021 (9)	0.0027 (9)
C9	0.0179 (12)	0.0180 (11)	0.0161 (12)	−0.0028 (9)	0.0008 (10)	−0.0028 (9)
C10	0.0157 (11)	0.0143 (10)	0.0198 (12)	−0.0026 (9)	0.0015 (10)	−0.0014 (10)
C11	0.0253 (13)	0.0177 (11)	0.0156 (12)	−0.0015 (10)	0.0002 (10)	−0.0024 (9)
C12	0.0179 (12)	0.0256 (13)	0.0222 (13)	0.0013 (10)	0.0006 (10)	−0.0017 (10)
C13	0.0200 (13)	0.0276 (13)	0.0252 (13)	0.0024 (11)	0.0009 (11)	−0.0012 (11)
C14	0.0212 (13)	0.0163 (11)	0.0185 (12)	−0.0019 (10)	−0.0015 (10)	0.0006 (9)
C15	0.0462 (17)	0.0213 (13)	0.0202 (13)	−0.0011 (12)	−0.0030 (12)	0.0042 (11)
C16	0.0414 (17)	0.0261 (14)	0.0237 (14)	−0.0019 (13)	−0.0047 (12)	0.0027 (11)

Geometric parameters (Å, º)

Pd—N2	2.0164 (19)	F4—C16	1.356 (3)
Pd—N1	2.0342 (19)	C5—H5	0.9300
Pd—Cl1	2.2855 (6)	C6—C7	1.382 (3)
Pd—Cl2	2.2999 (6)	C7—C8	1.392 (3)
F1—C13	1.374 (3)	C7—H7	0.9300
F2—C13	1.370 (3)	C8—C9	1.387 (3)
F3—C16	1.360 (3)	C8—C14	1.499 (3)
O1—C11	1.421 (3)	C9—C10	1.382 (3)
O1—C12	1.425 (3)	C9—H9	0.9300
O2—C15	1.410 (3)	C10—H10	0.9300
O2—C14	1.414 (3)	C11—H11A	0.9700
N1—C5	1.339 (3)	C11—H11B	0.9700
N1—C1	1.362 (3)	C12—C13	1.491 (4)
N2—C10	1.342 (3)	C12—H12A	0.9700
N2—C6	1.363 (3)	C12—H12B	0.9700
C1—C2	1.389 (3)	C13—H13	1.00 (3)
C1—C6	1.469 (3)	C14—H14A	0.9700
C2—C3	1.387 (3)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.479 (4)
C3—C4	1.389 (3)	C15—H15A	0.9700
C3—C11	1.514 (3)	C15—H15B	0.9700
C4—C5	1.382 (3)	C16—H16	1.08 (3)
C4—H4	0.9300
N2—Pd—N1	80.76 (7)	C8—C9—H9	120.1
N2—Pd—Cl1	93.73 (5)	N2—C10—C9	122.0 (2)
N1—Pd—Cl1	172.24 (6)	N2—C10—H10	119.0
N2—Pd—Cl2	175.64 (6)	C9—C10—H10	119.0
N1—Pd—Cl2	95.15 (6)	O1—C11—C3	112.94 (19)
Cl1—Pd—Cl2	90.48 (2)	O1—C11—H11A	109.0
C11—O1—C12	112.38 (18)	C3—C11—H11A	109.0
C15—O2—C14	114.23 (18)	O1—C11—H11B	109.0
C5—N1—C1	119.0 (2)	C3—C11—H11B	109.0
C5—N1—Pd	127.00 (16)	H11A—C11—H11B	107.8
C1—N1—Pd	113.72 (15)	O1—C12—C13	108.3 (2)
C10—N2—C6	118.9 (2)	O1—C12—H12A	110.0
C10—N2—Pd	126.43 (15)	C13—C12—H12A	110.0
C6—N2—Pd	114.65 (15)	O1—C12—H12B	110.0
N1—C1—C2	121.2 (2)	C13—C12—H12B	110.0
N1—C1—C6	115.3 (2)	H12A—C12—H12B	108.4
C2—C1—C6	123.5 (2)	F2—C13—F1	104.6 (2)
C3—C2—C1	119.6 (2)	F2—C13—C12	110.6 (2)
C3—C2—H2	120.2	F1—C13—C12	110.5 (2)
C1—C2—H2	120.2	F2—C13—H13	108.0 (14)
C2—C3—C4	118.4 (2)	F1—C13—H13	109.1 (15)
C2—C3—C11	119.2 (2)	C12—C13—H13	113.6 (15)
C4—C3—C11	122.3 (2)	O2—C14—C8	108.98 (19)
C5—C4—C3	119.5 (2)	O2—C14—H14A	109.9
C5—C4—H4	120.2	C8—C14—H14A	109.9
C3—C4—H4	120.2	O2—C14—H14B	109.9
N1—C5—C4	122.1 (2)	C8—C14—H14B	109.9
N1—C5—H5	118.9	H14A—C14—H14B	108.3
C4—C5—H5	118.9	O2—C15—C16	106.6 (2)
N2—C6—C7	121.3 (2)	O2—C15—H15A	110.4
N2—C6—C1	114.8 (2)	C16—C15—H15A	110.4
C7—C6—C1	123.9 (2)	O2—C15—H15B	110.4
C6—C7—C8	119.8 (2)	C16—C15—H15B	110.4
C6—C7—H7	120.1	H15A—C15—H15B	108.6
C8—C7—H7	120.1	F4—C16—F3	106.3 (2)
C9—C8—C7	118.1 (2)	F4—C16—C15	110.7 (2)
C9—C8—C14	123.0 (2)	F3—C16—C15	110.3 (2)
C7—C8—C14	118.9 (2)	F4—C16—H16	110.1 (15)
C10—C9—C8	119.8 (2)	F3—C16—H16	107.9 (15)
C10—C9—H9	120.1	C15—C16—H16	111.4 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1^i	0.93	2.95	3.590 (2)	165
C5—H5···Cl2	0.93	2.70	3.283 (3)	121
C5—H5···F4^ii	0.93	2.56	3.248 (3)	131
C7—H7···Cl1^i	0.93	2.62	3.519 (3)	163
C9—H9···O2	0.93	2.39	2.721 (3)	101
C10—H10···Cl2^iii	0.93	2.94	3.679 (3)	137
C11—H11B···Cl2^i	0.97	2.91	3.832 (3)	159
C12—H12A···F3^iv	0.97	2.58	3.336 (3)	135
C12—H12B···Cl2^i	0.97	2.93	3.724 (3)	140
C13—H13···F1^v	1.01 (3)	2.59 (2)	3.263 (4)	124.1 (18)
C13—H13···O1^v	1.01 (2)	2.27 (2)	3.255 (3)	166.5 (19)
C13—F2···F4^vi	1.37 (1)	2.82 (1)	4.136 (3)	160 (1)
C14—H14B···Cl2^vii	0.97	2.75	3.662 (2)	158
C16—H16···F1^viii	1.09 (3)	2.53 (3)	3.248 (3)	123 (2)
C16—H16···F3^ix	1.09 (3)	2.31 (3)	3.227 (3)	141 (2)
C16—F4···F2^x	1.36 (1)	2.82 (1)	3.660 (3)	118 (1)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, −y+2, z+1/2; (iii) x−1/2, −y+3/2, −z+1; (iv) −x, −y+2, −z+1; (v) x−1/2, y, −z+3/2; (vi) x+1/2, −y+5/2, −z+1; (vii) −x+1, −y+2, −z+1; (viii) −x+1/2, −y+2, z−1/2; (ix) x+1/2, y, −z+1/2; (x) x−1/2, −y+5/2, −z+1.

(i16258)

Crystal data

C16H16Cl2F4N2O2Pt	Dx = 2.247 Mg m^−3
Mr = 610.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9856 reflections
a = 7.7215 (2) Å	θ = 2.6–32.5°
b = 16.5892 (4) Å	µ = 8.13 mm^−1
c = 28.1692 (7) Å	T = 100 K
V = 3608.29 (16) Å^3	Prism, yellow
Z = 8	0.25 × 0.21 × 0.09 mm
F(000) = 2320

Data collection

Bruker APEXII CCD diffractometer	3592 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.062
Absorption correction: numerical (SADABS; Bruker, 2015)	θmax = 27.1°, θmin = 2.5°
Tmin = 0.528, Tmax = 0.747	h = −9→8
84386 measured reflections	k = −21→21
3979 independent reflections	l = −35→36

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.043	w = 1/[σ^2(Fo^2) + 11.5571P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
3979 reflections	Δρmax = 0.82 e Å^−3
252 parameters	Δρmin = −1.23 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.

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

	x	y	z	Uiso*/Ueq
Pt1	0.42137 (2)	0.85730 (2)	0.54665 (2)	0.01157 (4)
Cl1	0.45804 (10)	0.74613 (5)	0.49958 (3)	0.01687 (16)
Cl2	0.56761 (10)	0.79290 (5)	0.60687 (3)	0.01711 (16)
F1	0.3387 (3)	1.15000 (14)	0.76924 (8)	0.0312 (5)
F2	0.3084 (3)	1.27987 (14)	0.76693 (8)	0.0341 (5)
F3	−0.1091 (3)	0.98013 (15)	0.26753 (9)	0.0426 (6)
F4	0.0152 (4)	1.08122 (16)	0.23232 (8)	0.0512 (7)
O1	0.3887 (3)	1.21668 (14)	0.68078 (8)	0.0161 (5)
O2	0.0153 (4)	1.03499 (14)	0.35420 (9)	0.0257 (6)
N1	0.3976 (3)	0.96340 (16)	0.58094 (9)	0.0126 (5)
N2	0.2895 (3)	0.91887 (15)	0.49699 (9)	0.0121 (5)
C1	0.3282 (4)	1.02399 (19)	0.55400 (11)	0.0112 (6)
C2	0.3204 (4)	1.10254 (19)	0.57030 (11)	0.0134 (6)
H2	0.2715	1.1437	0.5510	0.016*
C3	0.3847 (4)	1.12075 (19)	0.61510 (11)	0.0144 (6)
C4	0.4483 (4)	1.0582 (2)	0.64290 (12)	0.0169 (7)
H4	0.4885	1.0687	0.6742	0.020*
C5	0.4531 (4)	0.9807 (2)	0.62491 (12)	0.0162 (7)
H5	0.4970	0.9385	0.6442	0.019*
C6	0.2641 (4)	0.99847 (19)	0.50711 (11)	0.0119 (6)
C7	0.1857 (4)	1.04981 (18)	0.47518 (11)	0.0124 (6)
H7	0.1721	1.1053	0.4825	0.015*
C8	0.1269 (4)	1.01942 (19)	0.43221 (11)	0.0128 (6)
C9	0.1476 (4)	0.93767 (19)	0.42307 (11)	0.0137 (6)
H9	0.1060	0.9152	0.3942	0.016*
C10	0.2290 (4)	0.88928 (19)	0.45614 (11)	0.0148 (6)
H10	0.2423	0.8334	0.4496	0.018*
C11	0.3921 (4)	1.20787 (19)	0.63081 (11)	0.0169 (7)
H11A	0.4994	1.2327	0.6183	0.020*
H11B	0.2926	1.2372	0.6170	0.020*
C12	0.2194 (4)	1.2069 (2)	0.69995 (12)	0.0200 (7)
H12A	0.1702	1.1545	0.6898	0.024*
H12B	0.1425	1.2505	0.6884	0.024*
C13	0.2324 (5)	1.2098 (2)	0.75282 (13)	0.0235 (7)
C14	0.0484 (4)	1.07680 (19)	0.39690 (11)	0.0151 (6)
H14A	−0.0608	1.0992	0.4097	0.018*
H14B	0.1291	1.1221	0.3909	0.018*
C15	−0.0103 (6)	1.0862 (2)	0.31493 (13)	0.0277 (8)
H15A	0.0725	1.1318	0.3157	0.033*
H15B	−0.1296	1.1080	0.3149	0.033*
C16	0.0197 (6)	1.0353 (2)	0.27231 (14)	0.0301 (9)
H13	0.121 (5)	1.207 (2)	0.7684 (14)	0.022 (10)*
H16	0.141 (6)	1.006 (3)	0.2742 (17)	0.042 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01169 (6)	0.00935 (6)	0.01365 (6)	−0.00064 (4)	0.00126 (5)	0.00153 (4)
Cl1	0.0183 (4)	0.0103 (3)	0.0220 (4)	0.0010 (3)	−0.0018 (3)	−0.0019 (3)
Cl2	0.0185 (4)	0.0148 (4)	0.0180 (4)	0.0014 (3)	−0.0014 (3)	0.0039 (3)
F1	0.0307 (12)	0.0364 (13)	0.0263 (12)	0.0029 (10)	−0.0038 (9)	0.0077 (10)
F2	0.0422 (14)	0.0347 (13)	0.0255 (12)	−0.0002 (11)	0.0019 (10)	−0.0119 (10)
F3	0.0479 (15)	0.0378 (14)	0.0422 (15)	−0.0048 (12)	−0.0166 (12)	−0.0100 (11)
F4	0.097 (2)	0.0396 (15)	0.0168 (12)	0.0091 (15)	0.0028 (13)	0.0027 (10)
O1	0.0166 (11)	0.0204 (12)	0.0112 (11)	−0.0008 (9)	−0.0008 (9)	−0.0038 (9)
O2	0.0477 (16)	0.0147 (12)	0.0148 (12)	−0.0024 (11)	−0.0101 (11)	0.0017 (10)
N1	0.0126 (13)	0.0124 (12)	0.0129 (13)	−0.0010 (10)	0.0040 (10)	0.0015 (10)
N2	0.0110 (12)	0.0111 (12)	0.0142 (13)	−0.0029 (10)	0.0019 (10)	0.0012 (10)
C1	0.0097 (14)	0.0136 (15)	0.0103 (15)	−0.0011 (11)	0.0022 (11)	0.0029 (11)
C2	0.0138 (15)	0.0128 (15)	0.0135 (15)	0.0006 (12)	0.0033 (12)	0.0021 (12)
C3	0.0113 (15)	0.0164 (16)	0.0155 (16)	−0.0015 (12)	0.0030 (12)	−0.0010 (12)
C4	0.0187 (16)	0.0205 (17)	0.0114 (15)	−0.0013 (13)	0.0001 (13)	0.0000 (13)
C5	0.0166 (16)	0.0177 (16)	0.0143 (16)	0.0021 (13)	0.0018 (12)	0.0016 (12)
C6	0.0085 (14)	0.0123 (14)	0.0147 (15)	−0.0030 (11)	0.0034 (12)	0.0008 (12)
C7	0.0118 (14)	0.0107 (15)	0.0148 (16)	−0.0008 (11)	0.0028 (12)	0.0005 (12)
C8	0.0097 (14)	0.0143 (15)	0.0145 (15)	−0.0028 (12)	0.0014 (12)	0.0014 (12)
C9	0.0126 (15)	0.0145 (15)	0.0141 (15)	−0.0024 (12)	0.0003 (12)	−0.0011 (12)
C10	0.0132 (15)	0.0135 (14)	0.0177 (15)	−0.0025 (12)	0.0012 (13)	−0.0015 (13)
C11	0.0217 (17)	0.0155 (16)	0.0134 (16)	−0.0008 (13)	−0.0008 (13)	−0.0033 (12)
C12	0.0139 (16)	0.0266 (18)	0.0196 (17)	0.0019 (14)	−0.0012 (13)	−0.0019 (14)
C13	0.0190 (18)	0.0301 (19)	0.0213 (18)	0.0042 (15)	0.0007 (15)	−0.0027 (15)
C14	0.0168 (16)	0.0151 (15)	0.0134 (15)	0.0000 (13)	−0.0009 (12)	0.0000 (12)
C15	0.046 (2)	0.0213 (18)	0.0162 (18)	0.0031 (17)	−0.0047 (16)	0.0043 (14)
C16	0.045 (2)	0.026 (2)	0.0201 (19)	0.0000 (18)	−0.0025 (17)	0.0007 (16)

Geometric parameters (Å, º)

Pt1—N2	2.009 (3)	C7—C8	1.387 (4)
Pt1—N1	2.016 (3)	C8—C9	1.390 (4)
Pt1—Cl1	2.2891 (8)	C8—C14	1.504 (4)
Pt1—Cl2	2.3008 (8)	C9—C10	1.381 (5)
F1—C13	1.369 (4)	C12—C13	1.494 (5)
F2—C13	1.361 (4)	C15—C16	1.486 (5)
F3—C16	1.358 (5)	C2—H2	0.95
F4—C16	1.360 (5)	C4—H4	0.95
O1—C11	1.415 (4)	C5—H5	0.95
O1—C12	1.424 (4)	C7—H7	0.95
O2—C15	1.409 (4)	C9—H9	0.95
O2—C14	1.412 (4)	C10—H10	0.95
N1—C5	1.342 (4)	C11—H11A	0.99
N1—C1	1.369 (4)	C11—H11B	0.99
N2—C10	1.336 (4)	C12—H12A	0.99
N2—C6	1.365 (4)	C12—H12B	0.99
C1—C2	1.383 (4)	C13—H13	0.97 (4)
C1—C6	1.473 (4)	C14—H14A	0.99
C2—C3	1.389 (5)	C14—H14B	0.99
C3—C4	1.390 (5)	C15—H15A	0.99
C3—C11	1.513 (4)	C15—H15B	0.99
C4—C5	1.383 (5)	C16—H16	1.06 (5)
C6—C7	1.379 (4)
N2—Pt1—N1	81.00 (11)	F3—C16—C15	110.4 (4)
N2—Pt1—Cl1	93.95 (8)	F4—C16—C15	110.3 (3)
N1—Pt1—Cl1	172.83 (8)	C1—C2—H2	120
N2—Pt1—Cl2	176.43 (8)	C3—C2—H2	120
N1—Pt1—Cl2	95.57 (8)	C3—C4—H4	120
Cl1—Pt1—Cl2	89.55 (3)	C5—C4—H4	120
C11—O1—C12	112.5 (2)	N1—C5—H5	119
C15—O2—C14	113.5 (3)	C4—C5—H5	119
C5—N1—C1	118.7 (3)	C6—C7—H7	120
C5—N1—Pt1	126.9 (2)	C8—C7—H7	120
C1—N1—Pt1	114.3 (2)	C8—C9—H9	120
C10—N2—C6	119.0 (3)	C10—C9—H9	120
C10—N2—Pt1	126.2 (2)	N2—C10—H10	119
C6—N2—Pt1	114.8 (2)	C9—C10—H10	119
N1—C1—C2	121.7 (3)	O1—C11—H11A	109
N1—C1—C6	114.7 (3)	O1—C11—H11B	109
C2—C1—C6	123.6 (3)	C3—C11—H11A	109
C1—C2—C3	119.4 (3)	C3—C11—H11B	109
C2—C3—C4	118.4 (3)	H11A—C11—H11B	108
C2—C3—C11	119.2 (3)	O1—C12—H12A	110
C4—C3—C11	122.3 (3)	O1—C12—H12B	110
C5—C4—C3	119.8 (3)	C13—C12—H12A	110
N1—C5—C4	121.9 (3)	C13—C12—H12B	110
N2—C6—C7	121.6 (3)	H12A—C12—H12B	108
N2—C6—C1	114.7 (3)	F1—C13—H13	110 (2)
C7—C6—C1	123.7 (3)	F2—C13—H13	107 (2)
C6—C7—C8	119.2 (3)	C12—C13—H13	113 (2)
C7—C8—C9	118.6 (3)	O2—C14—H14A	110
C7—C8—C14	118.6 (3)	O2—C14—H14B	110
C9—C8—C14	122.8 (3)	C8—C14—H14A	110
C10—C9—C8	119.7 (3)	C8—C14—H14B	110
N2—C10—C9	121.8 (3)	H14A—C14—H14B	108
O1—C11—C3	112.9 (3)	O2—C15—H15A	111
O1—C12—C13	108.2 (3)	O2—C15—H15B	111
F2—C13—F1	105.2 (3)	C16—C15—H15A	111
F2—C13—C12	110.4 (3)	C16—C15—H15B	111
F1—C13—C12	110.7 (3)	H15A—C15—H15B	109
O2—C14—C8	109.0 (3)	F3—C16—H16	110 (3)
O2—C15—C16	105.6 (3)	F4—C16—H16	109 (3)
F3—C16—F4	106.1 (3)	C15—C16—H16	111 (3)