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The polyfluorinated title compounds, [MCl2(C16H16F4N2O2)] or [4,4′-(HCF2CH2OCH2)2-2,2′-bpy]MCl2 [M = Pd, (1), and M = Pt, (2)], have –C(Hα)2OC(Hβ)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—Hβ...F(—C) inter­actions (abbreviated as C—Hβ...F—C,C—Hβ...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—Hβ...F—C,C—Hβ...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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013857/ku3207sup1.cif
Contains datablocks i12726, i16258, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013857/ku3207i12726sup2.hkl
Contains datablock i12726

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013857/ku3207i16258sup3.hkl
Contains datablock i16258

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617013857/ku3207sup4.pdf
Additional figures and interaction information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013857/ku3207sup5.cif
CIF data for Pd complex at 200 K

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013857/ku3207sup6.cif
CIF data for Pt complex at 200 K

CCDC references: 1576472; 1576471

Computing details top

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) top
Crystal data top
[PdCl2(C16H16F4N2O2)]Dx = 1.916 Mg m3
Mr = 521.61Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9893 reflections
a = 7.7401 (2) Åθ = 2.6–32.1°
b = 16.5086 (4) ŵ = 1.38 mm1
c = 28.3013 (7) ÅT = 295 K
V = 3616.29 (16) Å3Prism, orange
Z = 80.24 × 0.22 × 0.18 mm
F(000) = 2064
Data collection top
Bruker APEXII CCD
diffractometer
3173 reflections with I > 2σ(I)
φ and ω scansRint = 0.054
Absorption correction: multi-scan
(SADABS; Bruker, 1996)
θmax = 26.4°, θmin = 2.5°
Tmin = 0.809, Tmax = 0.971h = 99
59415 measured reflectionsk = 2018
3702 independent reflectionsl = 3535
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.051 w = 1/[σ2(Fo2) + (0.0151P)2 + 5.2894P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
3702 reflectionsΔρmax = 0.43 e Å3
252 parametersΔρmin = 0.65 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Pd0.42460 (2)0.85543 (2)0.54593 (2)0.01366 (6)
Cl10.46751 (7)0.74610 (3)0.49780 (2)0.01877 (12)
Cl20.56776 (8)0.79099 (3)0.60642 (2)0.01849 (12)
F10.3347 (2)1.14754 (9)0.76921 (6)0.0320 (4)
F20.3056 (2)1.27837 (9)0.76749 (6)0.0345 (4)
F30.1033 (2)0.98226 (10)0.26759 (6)0.0411 (4)
O10.3825 (2)1.21584 (10)0.68130 (6)0.0191 (4)
O20.0185 (3)1.03653 (10)0.35459 (6)0.0279 (4)
N10.3954 (2)0.96204 (11)0.58108 (7)0.0150 (4)
N20.2923 (2)0.91795 (11)0.49658 (7)0.0148 (4)
C10.3267 (3)1.02234 (13)0.55416 (8)0.0151 (5)
C20.3170 (3)1.10138 (13)0.57079 (8)0.0153 (5)
H20.26951.14190.55200.018*
C30.3786 (3)1.11956 (14)0.61556 (8)0.0167 (5)
C40.4421 (3)1.05677 (14)0.64325 (9)0.0194 (5)
H40.47961.06680.67390.023*
F40.0223 (3)1.08427 (10)0.23322 (6)0.0496 (5)
C50.4493 (3)0.97926 (14)0.62490 (8)0.0185 (5)
H50.49310.93770.64360.022*
C60.2658 (3)0.99752 (13)0.50719 (8)0.0137 (4)
C70.1869 (3)1.04930 (13)0.47545 (8)0.0150 (5)
H70.17181.10360.48310.018*
C80.1301 (3)1.01992 (13)0.43203 (8)0.0146 (5)
C90.1518 (3)0.93813 (14)0.42258 (8)0.0173 (5)
H90.11140.91630.39440.021*
C100.2337 (3)0.88910 (14)0.45522 (8)0.0166 (5)
H100.24880.83450.44830.020*
C110.3848 (3)1.20713 (14)0.63135 (8)0.0196 (5)
H11A0.48881.23210.61900.023*
H11B0.28651.23570.61810.023*
C120.2140 (3)1.20527 (16)0.70064 (9)0.0219 (5)
H12A0.16651.15360.69070.026*
H12B0.13791.24800.68960.026*
C130.2277 (3)1.20801 (16)0.75317 (10)0.0242 (5)
C140.0510 (3)1.07784 (14)0.39745 (8)0.0187 (5)
H14A0.05611.09920.41010.022*
H14B0.12901.12280.39190.022*
C150.0052 (4)1.08781 (15)0.31527 (9)0.0292 (6)
H15A0.07581.13260.31640.035*
H15B0.12171.10950.31500.035*
C160.0252 (4)1.03779 (16)0.27273 (10)0.0304 (6)
H130.113 (3)1.2038 (15)0.7697 (9)0.019 (7)*
H160.147 (4)1.0054 (17)0.2750 (10)0.030 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd0.01440 (9)0.01048 (9)0.01611 (9)0.00037 (7)0.00104 (7)0.00137 (7)
Cl10.0206 (3)0.0115 (2)0.0242 (3)0.0008 (2)0.0018 (2)0.0021 (2)
Cl20.0211 (3)0.0155 (3)0.0189 (3)0.0016 (2)0.0016 (2)0.0038 (2)
F10.0312 (9)0.0347 (9)0.0301 (8)0.0025 (7)0.0041 (7)0.0072 (7)
F20.0437 (10)0.0314 (8)0.0285 (9)0.0005 (7)0.0006 (7)0.0122 (7)
F30.0461 (11)0.0347 (9)0.0424 (10)0.0044 (8)0.0147 (8)0.0086 (8)
O10.0188 (9)0.0227 (9)0.0158 (8)0.0007 (7)0.0003 (7)0.0041 (7)
O20.0494 (12)0.0169 (8)0.0174 (9)0.0048 (8)0.0101 (8)0.0028 (7)
N10.0161 (10)0.0136 (9)0.0152 (10)0.0009 (8)0.0021 (8)0.0018 (8)
N20.0150 (9)0.0119 (9)0.0176 (10)0.0018 (7)0.0026 (8)0.0003 (8)
C10.0125 (11)0.0148 (11)0.0181 (12)0.0008 (9)0.0018 (9)0.0025 (9)
C20.0151 (11)0.0146 (11)0.0162 (12)0.0002 (9)0.0023 (9)0.0024 (9)
C30.0167 (12)0.0165 (11)0.0170 (12)0.0016 (9)0.0035 (9)0.0020 (9)
C40.0211 (12)0.0208 (12)0.0162 (12)0.0002 (10)0.0001 (10)0.0016 (10)
F40.0931 (16)0.0382 (10)0.0176 (8)0.0061 (10)0.0008 (9)0.0021 (7)
C50.0200 (12)0.0195 (12)0.0161 (12)0.0023 (10)0.0006 (10)0.0010 (9)
C60.0107 (10)0.0133 (10)0.0172 (12)0.0018 (9)0.0040 (9)0.0001 (9)
C70.0140 (11)0.0117 (10)0.0191 (12)0.0016 (8)0.0026 (9)0.0002 (9)
C80.0114 (11)0.0157 (11)0.0167 (12)0.0013 (9)0.0021 (9)0.0027 (9)
C90.0179 (12)0.0180 (11)0.0161 (12)0.0028 (9)0.0008 (10)0.0028 (9)
C100.0157 (11)0.0143 (10)0.0198 (12)0.0026 (9)0.0015 (10)0.0014 (10)
C110.0253 (13)0.0177 (11)0.0156 (12)0.0015 (10)0.0002 (10)0.0024 (9)
C120.0179 (12)0.0256 (13)0.0222 (13)0.0013 (10)0.0006 (10)0.0017 (10)
C130.0200 (13)0.0276 (13)0.0252 (13)0.0024 (11)0.0009 (11)0.0012 (11)
C140.0212 (13)0.0163 (11)0.0185 (12)0.0019 (10)0.0015 (10)0.0006 (9)
C150.0462 (17)0.0213 (13)0.0202 (13)0.0011 (12)0.0030 (12)0.0042 (11)
C160.0414 (17)0.0261 (14)0.0237 (14)0.0019 (13)0.0047 (12)0.0027 (11)
Geometric parameters (Å, º) top
Pd—N22.0164 (19)F4—C161.356 (3)
Pd—N12.0342 (19)C5—H50.9300
Pd—Cl12.2855 (6)C6—C71.382 (3)
Pd—Cl22.2999 (6)C7—C81.392 (3)
F1—C131.374 (3)C7—H70.9300
F2—C131.370 (3)C8—C91.387 (3)
F3—C161.360 (3)C8—C141.499 (3)
O1—C111.421 (3)C9—C101.382 (3)
O1—C121.425 (3)C9—H90.9300
O2—C151.410 (3)C10—H100.9300
O2—C141.414 (3)C11—H11A0.9700
N1—C51.339 (3)C11—H11B0.9700
N1—C11.362 (3)C12—C131.491 (4)
N2—C101.342 (3)C12—H12A0.9700
N2—C61.363 (3)C12—H12B0.9700
C1—C21.389 (3)C13—H131.00 (3)
C1—C61.469 (3)C14—H14A0.9700
C2—C31.387 (3)C14—H14B0.9700
C2—H20.9300C15—C161.479 (4)
C3—C41.389 (3)C15—H15A0.9700
C3—C111.514 (3)C15—H15B0.9700
C4—C51.382 (3)C16—H161.08 (3)
C4—H40.9300
N2—Pd—N180.76 (7)C8—C9—H9120.1
N2—Pd—Cl193.73 (5)N2—C10—C9122.0 (2)
N1—Pd—Cl1172.24 (6)N2—C10—H10119.0
N2—Pd—Cl2175.64 (6)C9—C10—H10119.0
N1—Pd—Cl295.15 (6)O1—C11—C3112.94 (19)
Cl1—Pd—Cl290.48 (2)O1—C11—H11A109.0
C11—O1—C12112.38 (18)C3—C11—H11A109.0
C15—O2—C14114.23 (18)O1—C11—H11B109.0
C5—N1—C1119.0 (2)C3—C11—H11B109.0
C5—N1—Pd127.00 (16)H11A—C11—H11B107.8
C1—N1—Pd113.72 (15)O1—C12—C13108.3 (2)
C10—N2—C6118.9 (2)O1—C12—H12A110.0
C10—N2—Pd126.43 (15)C13—C12—H12A110.0
C6—N2—Pd114.65 (15)O1—C12—H12B110.0
N1—C1—C2121.2 (2)C13—C12—H12B110.0
N1—C1—C6115.3 (2)H12A—C12—H12B108.4
C2—C1—C6123.5 (2)F2—C13—F1104.6 (2)
C3—C2—C1119.6 (2)F2—C13—C12110.6 (2)
C3—C2—H2120.2F1—C13—C12110.5 (2)
C1—C2—H2120.2F2—C13—H13108.0 (14)
C2—C3—C4118.4 (2)F1—C13—H13109.1 (15)
C2—C3—C11119.2 (2)C12—C13—H13113.6 (15)
C4—C3—C11122.3 (2)O2—C14—C8108.98 (19)
C5—C4—C3119.5 (2)O2—C14—H14A109.9
C5—C4—H4120.2C8—C14—H14A109.9
C3—C4—H4120.2O2—C14—H14B109.9
N1—C5—C4122.1 (2)C8—C14—H14B109.9
N1—C5—H5118.9H14A—C14—H14B108.3
C4—C5—H5118.9O2—C15—C16106.6 (2)
N2—C6—C7121.3 (2)O2—C15—H15A110.4
N2—C6—C1114.8 (2)C16—C15—H15A110.4
C7—C6—C1123.9 (2)O2—C15—H15B110.4
C6—C7—C8119.8 (2)C16—C15—H15B110.4
C6—C7—H7120.1H15A—C15—H15B108.6
C8—C7—H7120.1F4—C16—F3106.3 (2)
C9—C8—C7118.1 (2)F4—C16—C15110.7 (2)
C9—C8—C14123.0 (2)F3—C16—C15110.3 (2)
C7—C8—C14118.9 (2)F4—C16—H16110.1 (15)
C10—C9—C8119.8 (2)F3—C16—H16107.9 (15)
C10—C9—H9120.1C15—C16—H16111.4 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.932.953.590 (2)165
C5—H5···Cl20.932.703.283 (3)121
C5—H5···F4ii0.932.563.248 (3)131
C7—H7···Cl1i0.932.623.519 (3)163
C9—H9···O20.932.392.721 (3)101
C10—H10···Cl2iii0.932.943.679 (3)137
C11—H11B···Cl2i0.972.913.832 (3)159
C12—H12A···F3iv0.972.583.336 (3)135
C12—H12B···Cl2i0.972.933.724 (3)140
C13—H13···F1v1.01 (3)2.59 (2)3.263 (4)124.1 (18)
C13—H13···O1v1.01 (2)2.27 (2)3.255 (3)166.5 (19)
C13—F2···F4vi1.37 (1)2.82 (1)4.136 (3)160 (1)
C14—H14B···Cl2vii0.972.753.662 (2)158
C16—H16···F1viii1.09 (3)2.53 (3)3.248 (3)123 (2)
C16—H16···F3ix1.09 (3)2.31 (3)3.227 (3)141 (2)
C16—F4···F2x1.36 (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) x1/2, y+3/2, z+1; (iv) x, y+2, z+1; (v) x1/2, 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, z1/2; (ix) x+1/2, y, z+1/2; (x) x1/2, y+5/2, z+1.
(i16258) top
Crystal data top
C16H16Cl2F4N2O2PtDx = 2.247 Mg m3
Mr = 610.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9856 reflections
a = 7.7215 (2) Åθ = 2.6–32.5°
b = 16.5892 (4) ŵ = 8.13 mm1
c = 28.1692 (7) ÅT = 100 K
V = 3608.29 (16) Å3Prism, yellow
Z = 80.25 × 0.21 × 0.09 mm
F(000) = 2320
Data collection top
Bruker APEXII CCD
diffractometer
3592 reflections with I > 2σ(I)
φ and ω scansRint = 0.062
Absorption correction: numerical
(SADABS; Bruker, 2015)
θmax = 27.1°, θmin = 2.5°
Tmin = 0.528, Tmax = 0.747h = 98
84386 measured reflectionsk = 2121
3979 independent reflectionsl = 3536
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.020H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.043 w = 1/[σ2(Fo2) + 11.5571P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
3979 reflectionsΔρmax = 0.82 e Å3
252 parametersΔρmin = 1.23 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Pt10.42137 (2)0.85730 (2)0.54665 (2)0.01157 (4)
Cl10.45804 (10)0.74613 (5)0.49958 (3)0.01687 (16)
Cl20.56761 (10)0.79290 (5)0.60687 (3)0.01711 (16)
F10.3387 (3)1.15000 (14)0.76924 (8)0.0312 (5)
F20.3084 (3)1.27987 (14)0.76693 (8)0.0341 (5)
F30.1091 (3)0.98013 (15)0.26753 (9)0.0426 (6)
F40.0152 (4)1.08122 (16)0.23232 (8)0.0512 (7)
O10.3887 (3)1.21668 (14)0.68078 (8)0.0161 (5)
O20.0153 (4)1.03499 (14)0.35420 (9)0.0257 (6)
N10.3976 (3)0.96340 (16)0.58094 (9)0.0126 (5)
N20.2895 (3)0.91887 (15)0.49699 (9)0.0121 (5)
C10.3282 (4)1.02399 (19)0.55400 (11)0.0112 (6)
C20.3204 (4)1.10254 (19)0.57030 (11)0.0134 (6)
H20.27151.14370.55100.016*
C30.3847 (4)1.12075 (19)0.61510 (11)0.0144 (6)
C40.4483 (4)1.0582 (2)0.64290 (12)0.0169 (7)
H40.48851.06870.67420.020*
C50.4531 (4)0.9807 (2)0.62491 (12)0.0162 (7)
H50.49700.93850.64420.019*
C60.2641 (4)0.99847 (19)0.50711 (11)0.0119 (6)
C70.1857 (4)1.04981 (18)0.47518 (11)0.0124 (6)
H70.17211.10530.48250.015*
C80.1269 (4)1.01942 (19)0.43221 (11)0.0128 (6)
C90.1476 (4)0.93767 (19)0.42307 (11)0.0137 (6)
H90.10600.91520.39420.016*
C100.2290 (4)0.88928 (19)0.45614 (11)0.0148 (6)
H100.24230.83340.44960.018*
C110.3921 (4)1.20787 (19)0.63081 (11)0.0169 (7)
H11A0.49941.23270.61830.020*
H11B0.29261.23720.61700.020*
C120.2194 (4)1.2069 (2)0.69995 (12)0.0200 (7)
H12A0.17021.15450.68980.024*
H12B0.14251.25050.68840.024*
C130.2324 (5)1.2098 (2)0.75282 (13)0.0235 (7)
C140.0484 (4)1.07680 (19)0.39690 (11)0.0151 (6)
H14A0.06081.09920.40970.018*
H14B0.12911.12210.39090.018*
C150.0103 (6)1.0862 (2)0.31493 (13)0.0277 (8)
H15A0.07251.13180.31570.033*
H15B0.12961.10800.31490.033*
C160.0197 (6)1.0353 (2)0.27231 (14)0.0301 (9)
H130.121 (5)1.207 (2)0.7684 (14)0.022 (10)*
H160.141 (6)1.006 (3)0.2742 (17)0.042 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.01169 (6)0.00935 (6)0.01365 (6)0.00064 (4)0.00126 (5)0.00153 (4)
Cl10.0183 (4)0.0103 (3)0.0220 (4)0.0010 (3)0.0018 (3)0.0019 (3)
Cl20.0185 (4)0.0148 (4)0.0180 (4)0.0014 (3)0.0014 (3)0.0039 (3)
F10.0307 (12)0.0364 (13)0.0263 (12)0.0029 (10)0.0038 (9)0.0077 (10)
F20.0422 (14)0.0347 (13)0.0255 (12)0.0002 (11)0.0019 (10)0.0119 (10)
F30.0479 (15)0.0378 (14)0.0422 (15)0.0048 (12)0.0166 (12)0.0100 (11)
F40.097 (2)0.0396 (15)0.0168 (12)0.0091 (15)0.0028 (13)0.0027 (10)
O10.0166 (11)0.0204 (12)0.0112 (11)0.0008 (9)0.0008 (9)0.0038 (9)
O20.0477 (16)0.0147 (12)0.0148 (12)0.0024 (11)0.0101 (11)0.0017 (10)
N10.0126 (13)0.0124 (12)0.0129 (13)0.0010 (10)0.0040 (10)0.0015 (10)
N20.0110 (12)0.0111 (12)0.0142 (13)0.0029 (10)0.0019 (10)0.0012 (10)
C10.0097 (14)0.0136 (15)0.0103 (15)0.0011 (11)0.0022 (11)0.0029 (11)
C20.0138 (15)0.0128 (15)0.0135 (15)0.0006 (12)0.0033 (12)0.0021 (12)
C30.0113 (15)0.0164 (16)0.0155 (16)0.0015 (12)0.0030 (12)0.0010 (12)
C40.0187 (16)0.0205 (17)0.0114 (15)0.0013 (13)0.0001 (13)0.0000 (13)
C50.0166 (16)0.0177 (16)0.0143 (16)0.0021 (13)0.0018 (12)0.0016 (12)
C60.0085 (14)0.0123 (14)0.0147 (15)0.0030 (11)0.0034 (12)0.0008 (12)
C70.0118 (14)0.0107 (15)0.0148 (16)0.0008 (11)0.0028 (12)0.0005 (12)
C80.0097 (14)0.0143 (15)0.0145 (15)0.0028 (12)0.0014 (12)0.0014 (12)
C90.0126 (15)0.0145 (15)0.0141 (15)0.0024 (12)0.0003 (12)0.0011 (12)
C100.0132 (15)0.0135 (14)0.0177 (15)0.0025 (12)0.0012 (13)0.0015 (13)
C110.0217 (17)0.0155 (16)0.0134 (16)0.0008 (13)0.0008 (13)0.0033 (12)
C120.0139 (16)0.0266 (18)0.0196 (17)0.0019 (14)0.0012 (13)0.0019 (14)
C130.0190 (18)0.0301 (19)0.0213 (18)0.0042 (15)0.0007 (15)0.0027 (15)
C140.0168 (16)0.0151 (15)0.0134 (15)0.0000 (13)0.0009 (12)0.0000 (12)
C150.046 (2)0.0213 (18)0.0162 (18)0.0031 (17)0.0047 (16)0.0043 (14)
C160.045 (2)0.026 (2)0.0201 (19)0.0000 (18)0.0025 (17)0.0007 (16)
Geometric parameters (Å, º) top
Pt1—N22.009 (3)C7—C81.387 (4)
Pt1—N12.016 (3)C8—C91.390 (4)
Pt1—Cl12.2891 (8)C8—C141.504 (4)
Pt1—Cl22.3008 (8)C9—C101.381 (5)
F1—C131.369 (4)C12—C131.494 (5)
F2—C131.361 (4)C15—C161.486 (5)
F3—C161.358 (5)C2—H20.95
F4—C161.360 (5)C4—H40.95
O1—C111.415 (4)C5—H50.95
O1—C121.424 (4)C7—H70.95
O2—C151.409 (4)C9—H90.95
O2—C141.412 (4)C10—H100.95
N1—C51.342 (4)C11—H11A0.99
N1—C11.369 (4)C11—H11B0.99
N2—C101.336 (4)C12—H12A0.99
N2—C61.365 (4)C12—H12B0.99
C1—C21.383 (4)C13—H130.97 (4)
C1—C61.473 (4)C14—H14A0.99
C2—C31.389 (5)C14—H14B0.99
C3—C41.390 (5)C15—H15A0.99
C3—C111.513 (4)C15—H15B0.99
C4—C51.383 (5)C16—H161.06 (5)
C6—C71.379 (4)
N2—Pt1—N181.00 (11)F3—C16—C15110.4 (4)
N2—Pt1—Cl193.95 (8)F4—C16—C15110.3 (3)
N1—Pt1—Cl1172.83 (8)C1—C2—H2120
N2—Pt1—Cl2176.43 (8)C3—C2—H2120
N1—Pt1—Cl295.57 (8)C3—C4—H4120
Cl1—Pt1—Cl289.55 (3)C5—C4—H4120
C11—O1—C12112.5 (2)N1—C5—H5119
C15—O2—C14113.5 (3)C4—C5—H5119
C5—N1—C1118.7 (3)C6—C7—H7120
C5—N1—Pt1126.9 (2)C8—C7—H7120
C1—N1—Pt1114.3 (2)C8—C9—H9120
C10—N2—C6119.0 (3)C10—C9—H9120
C10—N2—Pt1126.2 (2)N2—C10—H10119
C6—N2—Pt1114.8 (2)C9—C10—H10119
N1—C1—C2121.7 (3)O1—C11—H11A109
N1—C1—C6114.7 (3)O1—C11—H11B109
C2—C1—C6123.6 (3)C3—C11—H11A109
C1—C2—C3119.4 (3)C3—C11—H11B109
C2—C3—C4118.4 (3)H11A—C11—H11B108
C2—C3—C11119.2 (3)O1—C12—H12A110
C4—C3—C11122.3 (3)O1—C12—H12B110
C5—C4—C3119.8 (3)C13—C12—H12A110
N1—C5—C4121.9 (3)C13—C12—H12B110
N2—C6—C7121.6 (3)H12A—C12—H12B108
N2—C6—C1114.7 (3)F1—C13—H13110 (2)
C7—C6—C1123.7 (3)F2—C13—H13107 (2)
C6—C7—C8119.2 (3)C12—C13—H13113 (2)
C7—C8—C9118.6 (3)O2—C14—H14A110
C7—C8—C14118.6 (3)O2—C14—H14B110
C9—C8—C14122.8 (3)C8—C14—H14A110
C10—C9—C8119.7 (3)C8—C14—H14B110
N2—C10—C9121.8 (3)H14A—C14—H14B108
O1—C11—C3112.9 (3)O2—C15—H15A111
O1—C12—C13108.2 (3)O2—C15—H15B111
F2—C13—F1105.2 (3)C16—C15—H15A111
F2—C13—C12110.4 (3)C16—C15—H15B111
F1—C13—C12110.7 (3)H15A—C15—H15B109
O2—C14—C8109.0 (3)F3—C16—H16110 (3)
O2—C15—C16105.6 (3)F4—C16—H16109 (3)
F3—C16—F4106.1 (3)C15—C16—H16111 (3)
 

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