Hydrogen bonding and fluorous weak inter­actions in the non-isomorphous {4,4′-bis­[(2,2,3,3-tetra­fluoro­prop­oxy)meth­yl]-2,2′-bi­pyridine-κ²N,N′}di­bromido­palladium and -platinum complexes

The polyfluorinated title compounds, [MBr₂(C₁₈H₁₆F₈N₂O₂)] or [4,4′-(HCF₂CF₂CH₂OCH₂)₂-2,2′-bpy]MBr₂, (1) (M = Pd and bpy is bipyridine) and (2) (M = Pt), have –CH_(α)2OCH_(β)2CF₂CF₂H side chains with methyl­ene H-atom donors at the α and β sites, and methine H-atom donors at the terminal sites, in addition to aromatic H-atom donors. In contrast to the original expectation of iso­morphous structures, (1) crystallizes in the space group C2/c and (2) in P2₁/n, with similar unit-cell volumes and Z = 4. The asymmetric unit of (1) is one half of the mol­ecule, which resides on a crystallographic twofold axis. Both (1) and (2) display stacking of the mol­ecules, indicating a planar (bpy)MBr₂ skeleton in each case. The structure of (1) exhibits columns with C—H_(β)...Br hydrogen bonds between consecutive layers which conforms to a static (β,β) linkage between layers. In the mol­ecular plane, (1) shows double C—H_(α)...Br hydrogen bonds self-repeating along the b axis, the planar molecules being connected into infinite belts. Compound (2) has no crystallographic symmetry and forms π-dimer pairs as supermolecules, which then stack parallel to the a axis. The π-dimer-pair super­molecules exhibit (Pt—)Br...Br(—Pt) contacts [3.6937 (7) Å] to neighbouring π-dimer pairs crosslinking the columns. The structure of (2) reveals many C—H...F(—C) inter­actions between F atoms and aromatic C—H groups, in addition to those between F atoms and methyl­ene C—H groups.

Computing details

Data collection: APEX3 (Bruker, 2015) for i12782; APEX2 (Bruker, 2015) for i15498. Cell refinement: APEX3 (Bruker, 2015) for i12782; SAINT (Bruker, 2015) for i15498. For both structures, data reduction: SAINT (Bruker, 2015). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for i12782; SHELXS97 (Sheldrick, 2008) for i15498. For both structures, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b). Molecular graphics: shelXle (Hübschle et al., 2011) for i12782; SHELXTL (Sheldrick, 2008) for i15498. Software used to prepare material for publication: WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008) for i12782; SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008) for i15498.

{4,4'-Bis[(2,2,3,3-tetrafluoropropoxy)methyl]-2,2'-bipyridine-κ²N,N'}dibromidopalladium (i12782)

Crystal data

[PdBr2(C18H16F8N2O2)]	F(000) = 1368
Mr = 710.55	Dx = 2.114 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.0989 (7) Å	Cell parameters from 8599 reflections
b = 9.7107 (3) Å	θ = 2.3–26.4°
c = 9.5630 (3) Å	µ = 4.50 mm^−1
β = 93.819 (2)°	T = 295 K
V = 2232.94 (12) Å^3	Prism, orange
Z = 4	0.18 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer	2062 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.024
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θmax = 26.4°, θmin = 2.3°
Tmin = 0.618, Tmax = 0.745	h = −30→28
19843 measured reflections	k = −11→12
2275 independent reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0334P)^2 + 6.1015P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2275 reflections	Δρmax = 0.73 e Å^−3
153 parameters	Δρmin = −0.72 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
Pd1	0.500000	0.31069 (3)	0.750000	0.02942 (10)
Br1	0.45416 (2)	0.13376 (3)	0.60961 (4)	0.04608 (12)
F1	0.25678 (11)	0.9736 (4)	0.1191 (3)	0.0964 (11)
F2	0.28718 (14)	0.7675 (5)	0.1241 (4)	0.1429 (19)
F3	0.20657 (14)	0.9294 (7)	0.3492 (5)	0.178 (3)
F4	0.18172 (12)	0.7861 (4)	0.1882 (4)	0.1008 (11)
O1	0.33803 (9)	0.8051 (2)	0.3838 (2)	0.0433 (5)
N1	0.46099 (9)	0.4704 (2)	0.6461 (2)	0.0284 (5)
C2	0.47739 (10)	0.5974 (3)	0.6933 (3)	0.0251 (5)
C3	0.45311 (10)	0.7156 (3)	0.6391 (3)	0.0263 (5)
H3	0.464562	0.801078	0.674029	0.032*
C4	0.41104 (11)	0.7067 (3)	0.5312 (3)	0.0280 (6)
C5	0.39553 (11)	0.5775 (3)	0.4837 (3)	0.0331 (6)
H5	0.368065	0.567859	0.411320	0.040*
C6	0.42071 (11)	0.4629 (3)	0.5434 (3)	0.0333 (6)
H6	0.409253	0.376521	0.511016	0.040*
C7	0.38622 (12)	0.8361 (3)	0.4717 (3)	0.0329 (6)
H7A	0.376370	0.896402	0.547059	0.039*
H7B	0.413143	0.883560	0.418021	0.039*
C8	0.32082 (13)	0.9193 (4)	0.3009 (3)	0.0440 (7)
H8A	0.350769	0.950514	0.245859	0.053*
H8B	0.309876	0.994686	0.359704	0.053*
C9	0.27238 (15)	0.8717 (4)	0.2070 (4)	0.0532 (9)
C10	0.2238 (2)	0.8236 (6)	0.2794 (5)	0.0779 (15)
H10	0.224 (2)	0.770 (6)	0.359 (6)	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.02884 (16)	0.01931 (16)	0.04132 (18)	0.000	0.01131 (12)	0.000
Br1	0.0480 (2)	0.02557 (18)	0.0661 (2)	−0.00933 (12)	0.01380 (16)	−0.01196 (14)
F1	0.0716 (16)	0.136 (3)	0.0766 (17)	−0.0089 (17)	−0.0283 (13)	0.0629 (18)
F2	0.106 (2)	0.215 (4)	0.100 (2)	0.077 (3)	−0.054 (2)	−0.109 (3)
F3	0.074 (2)	0.326 (8)	0.139 (3)	−0.069 (3)	0.052 (2)	−0.135 (5)
F4	0.0662 (17)	0.108 (2)	0.121 (2)	−0.0232 (16)	−0.0456 (17)	0.0030 (19)
O1	0.0409 (12)	0.0381 (12)	0.0477 (12)	−0.0027 (9)	−0.0208 (10)	0.0040 (10)
N1	0.0254 (11)	0.0254 (12)	0.0352 (12)	−0.0029 (9)	0.0066 (9)	−0.0052 (10)
C2	0.0238 (12)	0.0249 (13)	0.0272 (12)	−0.0025 (10)	0.0058 (10)	−0.0014 (10)
C3	0.0255 (12)	0.0240 (13)	0.0293 (12)	−0.0020 (10)	0.0007 (10)	−0.0021 (10)
C4	0.0244 (12)	0.0320 (15)	0.0276 (12)	0.0000 (10)	0.0024 (10)	−0.0031 (11)
C5	0.0274 (13)	0.0387 (16)	0.0324 (14)	−0.0047 (12)	−0.0028 (11)	−0.0073 (12)
C6	0.0301 (14)	0.0301 (15)	0.0396 (15)	−0.0052 (11)	0.0020 (11)	−0.0097 (12)
C7	0.0311 (14)	0.0334 (15)	0.0329 (14)	0.0000 (12)	−0.0071 (11)	−0.0023 (12)
C8	0.0383 (16)	0.053 (2)	0.0401 (16)	−0.0023 (15)	−0.0049 (13)	0.0124 (15)
C9	0.049 (2)	0.071 (3)	0.0371 (17)	0.0148 (18)	−0.0084 (15)	0.0021 (16)
C10	0.063 (3)	0.098 (4)	0.069 (3)	−0.030 (3)	−0.019 (2)	0.013 (3)

Geometric parameters (Å, º)

Pd1—N1	2.038 (2)	C3—C4	1.401 (3)
Pd1—N1^i	2.038 (2)	C3—H3	0.9300
Pd1—Br1	2.4035 (4)	C4—C5	1.378 (4)
Pd1—Br1^i	2.4035 (4)	C4—C7	1.489 (4)
F1—C9	1.337 (4)	C5—C6	1.373 (4)
F2—C9	1.348 (5)	C5—H5	0.9300
F3—C10	1.308 (8)	C6—H6	0.9300
F4—C10	1.343 (5)	C7—H7A	0.9700
O1—C8	1.409 (4)	C7—H7B	0.9700
O1—C7	1.420 (3)	C8—C9	1.498 (5)
N1—C6	1.336 (4)	C8—H8A	0.9700
N1—C2	1.363 (3)	C8—H8B	0.9700
C2—C3	1.373 (4)	C9—C10	1.475 (6)
C2—C2^i	1.486 (5)	C10—H10	0.92 (6)
N1—Pd1—N1^i	80.86 (13)	O1—C7—C4	109.8 (2)
N1—Pd1—Br1	95.27 (6)	O1—C7—H7A	109.7
N1^i—Pd1—Br1	175.13 (6)	C4—C7—H7A	109.7
N1—Pd1—Br1^i	175.13 (6)	O1—C7—H7B	109.7
N1^i—Pd1—Br1^i	95.27 (6)	C4—C7—H7B	109.7
Br1—Pd1—Br1^i	88.75 (2)	H7A—C7—H7B	108.2
C8—O1—C7	111.4 (2)	O1—C8—C9	106.4 (3)
C6—N1—C2	118.2 (2)	O1—C8—H8A	110.4
C6—N1—Pd1	127.30 (19)	C9—C8—H8A	110.4
C2—N1—Pd1	114.42 (18)	O1—C8—H8B	110.4
N1—C2—C3	121.6 (2)	C9—C8—H8B	110.4
N1—C2—C2^i	115.09 (15)	H8A—C8—H8B	108.6
C3—C2—C2^i	123.27 (15)	F1—C9—F2	105.0 (3)
C2—C3—C4	119.7 (3)	F1—C9—C10	109.3 (3)
C2—C3—H3	120.1	F2—C9—C10	106.8 (4)
C4—C3—H3	120.1	F1—C9—C8	108.9 (3)
C5—C4—C3	117.8 (3)	F2—C9—C8	111.0 (3)
C5—C4—C7	123.3 (2)	C10—C9—C8	115.3 (3)
C3—C4—C7	118.9 (2)	F3—C10—F4	107.0 (5)
C6—C5—C4	119.9 (2)	F3—C10—C9	106.2 (5)
C6—C5—H5	120.1	F4—C10—C9	111.7 (4)
C4—C5—H5	120.1	F3—C10—H10	90 (4)
N1—C6—C5	122.7 (3)	F4—C10—H10	110 (3)
N1—C6—H6	118.6	C9—C10—H10	127 (3)
C5—C6—H6	118.6
C6—N1—C2—C3	0.9 (4)	C8—O1—C7—C4	−166.4 (3)
Pd1—N1—C2—C3	−176.7 (2)	C5—C4—C7—O1	12.2 (4)
C6—N1—C2—C2^i	−179.6 (3)	C3—C4—C7—O1	−169.1 (2)
Pd1—N1—C2—C2^i	2.9 (3)	C7—O1—C8—C9	176.5 (3)
N1—C2—C3—C4	−1.1 (4)	O1—C8—C9—F1	−175.7 (3)
C2^i—C2—C3—C4	179.4 (3)	O1—C8—C9—F2	−60.6 (4)
C2—C3—C4—C5	0.2 (4)	O1—C8—C9—C10	61.0 (5)
C2—C3—C4—C7	−178.6 (2)	F1—C9—C10—F3	−61.0 (5)
C3—C4—C5—C6	0.8 (4)	F2—C9—C10—F3	−174.2 (4)
C7—C4—C5—C6	179.5 (3)	C8—C9—C10—F3	62.0 (6)
C2—N1—C6—C5	0.2 (4)	F1—C9—C10—F4	55.3 (6)
Pd1—N1—C6—C5	177.4 (2)	F2—C9—C10—F4	−57.8 (5)
C4—C5—C6—N1	−1.1 (4)	C8—C9—C10—F4	178.4 (4)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.42	2.746 (3)	100
C6—H6···Br1	0.93	2.73	3.346 (3)	124
C7—H7A···Br1^ii	0.97	3.01	3.534 (3)	116
C8—H8A···Br1^iii	0.97	3.00	3.837 (3)	145

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

{4,4'-Bis[(2,2,3,3-tetrafluoropropoxy)methyl]-2,2'-bipyridine-κ²N,N'}dibromidoplatinum (i15498)

Crystal data

[PtBr2(C18H16F8N2O2)]	F(000) = 1496
Mr = 799.24	Dx = 2.472 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.9344 (3) Å	Cell parameters from 9815 reflections
b = 11.8500 (5) Å	θ = 2.3–27.2°
c = 26.3196 (12) Å	µ = 10.34 mm^−1
β = 96.766 (2)°	T = 100 K
V = 2147.69 (16) Å^3	Plate, yellow
Z = 4	0.12 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	4462 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θmax = 27.1°, θmin = 1.9°
Tmin = 0.592, Tmax = 0.971	h = −8→8
77853 measured reflections	k = −15→15
4733 independent reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Only H-atom coordinates refined
wR(F^2) = 0.059	w = 1/[σ^2(Fo^2) + (0.0146P)^2 + 15.9277P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max = 0.001
4733 reflections	Δρmax = 1.26 e Å^−3
346 parameters	Δρmin = −0.99 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	0.17097 (2)	0.66847 (2)	0.46257 (2)	0.00863 (5)
Br1	0.08580 (6)	0.86348 (4)	0.47733 (2)	0.01307 (9)
Br2	0.13801 (7)	0.70814 (4)	0.37189 (2)	0.01582 (10)
F1	0.4760 (5)	0.0003 (3)	0.32226 (12)	0.0360 (9)
F2	0.7463 (5)	0.0793 (3)	0.35482 (13)	0.0320 (8)
F3	0.6165 (5)	−0.2007 (2)	0.37112 (13)	0.0262 (7)
F4	0.7671 (5)	−0.1303 (3)	0.31023 (11)	0.0257 (7)
F5	0.3600 (4)	0.3124 (2)	0.76645 (11)	0.0187 (6)
F6	0.6122 (4)	0.3424 (3)	0.82330 (10)	0.0212 (6)
F7	0.6045 (5)	0.1398 (3)	0.77658 (12)	0.0302 (7)
F8	0.8486 (5)	0.2464 (3)	0.76164 (14)	0.0346 (8)
O1	0.4694 (5)	0.1250 (3)	0.41236 (13)	0.0177 (7)
O2	0.5064 (5)	0.4550 (3)	0.69661 (12)	0.0170 (7)
N1	0.2415 (5)	0.5037 (3)	0.45526 (14)	0.0094 (7)
N2	0.2043 (5)	0.6225 (3)	0.53767 (14)	0.0103 (7)
C1	0.2731 (6)	0.4464 (4)	0.50052 (17)	0.0096 (8)
C2	0.3204 (6)	0.3327 (4)	0.50151 (17)	0.0115 (8)
H2	0.338 (7)	0.289 (5)	0.534 (2)	0.014*
C3	0.3368 (6)	0.2753 (4)	0.45611 (17)	0.0106 (8)
C4	0.3070 (6)	0.3353 (4)	0.41027 (18)	0.0130 (9)
H4	0.312 (8)	0.304 (5)	0.380 (2)	0.016*
C5	0.2591 (6)	0.4488 (4)	0.41165 (18)	0.0127 (9)
H5	0.240 (8)	0.491 (5)	0.385 (2)	0.015*
C6	0.2558 (6)	0.5133 (4)	0.54633 (17)	0.0106 (8)
C7	0.2881 (6)	0.4714 (4)	0.59569 (18)	0.0124 (9)
H7	0.319 (8)	0.397 (5)	0.599 (2)	0.015*
C8	0.2712 (6)	0.5416 (4)	0.63697 (17)	0.0135 (9)
C9	0.2185 (7)	0.6530 (4)	0.62751 (18)	0.0141 (9)
H9	0.205 (8)	0.706 (5)	0.652 (2)	0.017*
C10	0.1857 (6)	0.6909 (4)	0.57768 (17)	0.0108 (8)
H10	0.161 (8)	0.771 (5)	0.573 (2)	0.013*
C11	0.3895 (7)	0.1525 (4)	0.45747 (18)	0.0134 (9)
H11A	0.477 (8)	0.129 (5)	0.487 (2)	0.016*
H11B	0.280 (8)	0.111 (5)	0.461 (2)	0.016*
C12	0.5364 (7)	0.0127 (4)	0.41185 (18)	0.0134 (9)
H12A	0.436 (8)	−0.039 (5)	0.415 (2)	0.016*
H12B	0.646 (8)	0.005 (5)	0.443 (2)	0.016*
C13	0.6195 (7)	−0.0038 (4)	0.36220 (17)	0.0147 (9)
C14	0.7309 (7)	−0.1145 (4)	0.35903 (18)	0.0159 (9)
H14	0.841 (9)	−0.111 (5)	0.378 (2)	0.019*
C15	0.3119 (7)	0.4980 (5)	0.69104 (18)	0.0176 (10)
H15A	0.303 (8)	0.556 (5)	0.716 (2)	0.021*
H15B	0.219 (8)	0.443 (5)	0.698 (2)	0.021*
C16	0.5938 (8)	0.4476 (4)	0.74773 (19)	0.0195 (10)
H16A	0.555 (9)	0.503 (5)	0.773 (2)	0.023*
H16B	0.734 (9)	0.458 (5)	0.747 (2)	0.023*
C17	0.5543 (7)	0.3354 (4)	0.77188 (17)	0.0162 (9)
C18	0.6537 (7)	0.2341 (5)	0.7512 (2)	0.0202 (10)
H18	0.629 (8)	0.214 (5)	0.715 (2)	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.00835 (8)	0.00805 (8)	0.00931 (8)	0.00030 (6)	0.00037 (5)	0.00083 (6)
Br1	0.0166 (2)	0.0082 (2)	0.0141 (2)	0.00190 (16)	0.00047 (16)	0.00065 (16)
Br2	0.0218 (2)	0.0156 (2)	0.0105 (2)	0.00604 (18)	0.00360 (17)	0.00360 (17)
F1	0.045 (2)	0.041 (2)	0.0180 (16)	0.0288 (17)	−0.0119 (14)	−0.0054 (14)
F2	0.052 (2)	0.0134 (15)	0.0366 (19)	−0.0031 (14)	0.0292 (16)	−0.0005 (13)
F3	0.0286 (16)	0.0109 (14)	0.0396 (19)	−0.0003 (12)	0.0062 (14)	0.0013 (13)
F4	0.0375 (18)	0.0262 (16)	0.0134 (14)	0.0138 (14)	0.0033 (12)	−0.0044 (12)
F5	0.0189 (14)	0.0191 (15)	0.0182 (14)	−0.0012 (11)	0.0021 (11)	0.0035 (11)
F6	0.0299 (16)	0.0219 (15)	0.0104 (13)	0.0034 (13)	−0.0033 (11)	0.0001 (11)
F7	0.045 (2)	0.0172 (16)	0.0280 (17)	0.0070 (14)	0.0038 (15)	0.0031 (13)
F8	0.0229 (16)	0.044 (2)	0.0362 (19)	0.0099 (15)	0.0020 (14)	−0.0019 (16)
O1	0.0244 (18)	0.0128 (16)	0.0163 (17)	0.0069 (14)	0.0045 (14)	0.0021 (13)
O2	0.0164 (16)	0.0225 (18)	0.0114 (16)	0.0028 (14)	−0.0008 (13)	0.0041 (14)
N1	0.0083 (16)	0.0104 (18)	0.0094 (17)	0.0002 (14)	−0.0002 (13)	−0.0030 (14)
N2	0.0054 (16)	0.0105 (18)	0.0142 (18)	−0.0015 (14)	−0.0016 (13)	−0.0003 (15)
C1	0.0064 (18)	0.010 (2)	0.012 (2)	−0.0013 (15)	−0.0007 (15)	−0.0010 (16)
C2	0.0076 (19)	0.014 (2)	0.012 (2)	−0.0020 (16)	0.0018 (15)	0.0009 (18)
C3	0.0074 (19)	0.009 (2)	0.015 (2)	−0.0015 (15)	0.0000 (16)	−0.0032 (17)
C4	0.011 (2)	0.014 (2)	0.014 (2)	−0.0030 (17)	0.0002 (16)	−0.0046 (18)
C5	0.013 (2)	0.014 (2)	0.011 (2)	0.0001 (17)	−0.0013 (16)	0.0019 (18)
C6	0.0070 (18)	0.012 (2)	0.012 (2)	−0.0019 (16)	−0.0009 (15)	0.0011 (17)
C7	0.011 (2)	0.011 (2)	0.015 (2)	0.0013 (17)	0.0003 (16)	0.0017 (17)
C8	0.011 (2)	0.017 (2)	0.013 (2)	−0.0002 (17)	0.0026 (17)	0.0023 (18)
C9	0.013 (2)	0.015 (2)	0.015 (2)	−0.0004 (17)	0.0024 (17)	−0.0027 (18)
C10	0.011 (2)	0.011 (2)	0.010 (2)	−0.0008 (16)	0.0018 (16)	−0.0003 (16)
C11	0.016 (2)	0.009 (2)	0.016 (2)	0.0014 (18)	0.0043 (18)	−0.0005 (17)
C12	0.016 (2)	0.008 (2)	0.016 (2)	0.0010 (17)	0.0025 (18)	0.0004 (17)
C13	0.022 (2)	0.012 (2)	0.010 (2)	0.0034 (18)	0.0018 (17)	0.0020 (17)
C14	0.020 (2)	0.016 (2)	0.011 (2)	0.0005 (19)	−0.0004 (18)	−0.0010 (18)
C15	0.018 (2)	0.022 (3)	0.012 (2)	0.005 (2)	0.0013 (18)	0.005 (2)
C16	0.021 (3)	0.020 (3)	0.015 (2)	−0.005 (2)	−0.0072 (19)	0.002 (2)
C17	0.018 (2)	0.019 (2)	0.010 (2)	−0.0002 (19)	−0.0040 (17)	0.0009 (18)
C18	0.023 (2)	0.023 (3)	0.015 (2)	0.006 (2)	0.0015 (19)	−0.001 (2)

Geometric parameters (Å, º)

Pt1—N1	2.027 (4)	C4—C5	1.388 (7)
Pt1—N2	2.037 (4)	C4—H4	0.88 (6)
Pt1—Br2	2.4168 (5)	C5—H5	0.86 (6)
Pt1—Br1	2.4277 (5)	C6—C7	1.384 (6)
F1—C13	1.360 (5)	C7—C8	1.384 (7)
F2—C13	1.350 (6)	C7—H7	0.91 (6)
F3—C14	1.354 (6)	C8—C9	1.384 (7)
F4—C14	1.350 (5)	C8—C15	1.509 (6)
F5—C17	1.366 (6)	C9—C10	1.380 (6)
F6—C17	1.368 (5)	C9—H9	0.91 (6)
F7—C18	1.366 (6)	C10—H10	0.97 (6)
F8—C18	1.355 (6)	C11—H11A	0.98 (6)
O1—C11	1.406 (6)	C11—H11B	0.92 (6)
O1—C12	1.410 (5)	C12—C13	1.502 (6)
O2—C16	1.412 (6)	C12—H12A	0.94 (6)
O2—C15	1.433 (6)	C12—H12B	1.05 (6)
N1—C5	1.337 (6)	C13—C14	1.529 (7)
N1—C1	1.366 (6)	C14—H14	0.87 (6)
N2—C10	1.346 (6)	C15—H15A	0.96 (6)
N2—C6	1.355 (6)	C15—H15B	0.95 (6)
C1—C2	1.387 (6)	C16—C17	1.512 (7)
C1—C6	1.460 (6)	C16—H16A	1.00 (6)
C2—C3	1.391 (6)	C16—H16B	0.98 (6)
C2—H2	1.00 (6)	C17—C18	1.517 (7)
C3—C4	1.394 (6)	C18—H18	0.98 (6)
C3—C11	1.500 (6)
N1—Pt1—N2	80.43 (15)	C3—C11—H11A	115 (3)
N1—Pt1—Br2	95.13 (10)	O1—C11—H11B	112 (4)
N2—Pt1—Br2	175.56 (11)	C3—C11—H11B	109 (4)
N1—Pt1—Br1	176.19 (10)	H11A—C11—H11B	102 (5)
N2—Pt1—Br1	95.79 (11)	O1—C12—C13	107.0 (4)
Br2—Pt1—Br1	88.651 (16)	O1—C12—H12A	112 (3)
C11—O1—C12	112.9 (4)	C13—C12—H12A	111 (3)
C16—O2—C15	114.4 (4)	O1—C12—H12B	107 (3)
C5—N1—C1	119.0 (4)	C13—C12—H12B	110 (3)
C5—N1—Pt1	126.7 (3)	H12A—C12—H12B	110 (5)
C1—N1—Pt1	114.3 (3)	F2—C13—F1	107.0 (4)
C10—N2—C6	119.4 (4)	F2—C13—C12	110.7 (4)
C10—N2—Pt1	126.0 (3)	F1—C13—C12	110.3 (4)
C6—N2—Pt1	114.6 (3)	F2—C13—C14	106.0 (4)
N1—C1—C2	120.9 (4)	F1—C13—C14	108.5 (4)
N1—C1—C6	115.4 (4)	C12—C13—C14	114.1 (4)
C2—C1—C6	123.7 (4)	F4—C14—F3	107.3 (4)
C1—C2—C3	120.1 (4)	F4—C14—C13	108.9 (4)
C1—C2—H2	121 (3)	F3—C14—C13	108.7 (4)
C3—C2—H2	119 (3)	F4—C14—H14	108 (4)
C2—C3—C4	118.4 (4)	F3—C14—H14	114 (4)
C2—C3—C11	119.8 (4)	C13—C14—H14	110 (4)
C4—C3—C11	121.7 (4)	O2—C15—C8	106.7 (4)
C5—C4—C3	118.9 (4)	O2—C15—H15A	109 (4)
C5—C4—H4	118 (4)	C8—C15—H15A	112 (4)
C3—C4—H4	123 (4)	O2—C15—H15B	113 (4)
N1—C5—C4	122.7 (4)	C8—C15—H15B	111 (4)
N1—C5—H5	114 (4)	H15A—C15—H15B	105 (5)
C4—C5—H5	124 (4)	O2—C16—C17	112.1 (4)
N2—C6—C7	120.7 (4)	O2—C16—H16A	119 (3)
N2—C6—C1	115.2 (4)	C17—C16—H16A	103 (3)
C7—C6—C1	124.1 (4)	O2—C16—H16B	107 (4)
C6—C7—C8	120.2 (4)	C17—C16—H16B	110 (4)
C6—C7—H7	117 (4)	H16A—C16—H16B	106 (5)
C8—C7—H7	123 (4)	F5—C17—F6	106.7 (4)
C7—C8—C9	118.5 (4)	F5—C17—C16	110.9 (4)
C7—C8—C15	120.7 (4)	F6—C17—C16	108.4 (4)
C9—C8—C15	120.8 (4)	F5—C17—C18	106.8 (4)
C10—C9—C8	119.5 (4)	F6—C17—C18	108.1 (4)
C10—C9—H9	116 (4)	C16—C17—C18	115.6 (4)
C8—C9—H9	125 (4)	F8—C18—F7	106.8 (4)
N2—C10—C9	121.8 (4)	F8—C18—C17	109.1 (4)
N2—C10—H10	121 (3)	F7—C18—C17	108.7 (4)
C9—C10—H10	116 (3)	F8—C18—H18	106 (4)
O1—C11—C3	108.9 (4)	F7—C18—H18	105 (4)
O1—C11—H11A	110 (3)	C17—C18—H18	120 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.88 (5)	2.49 (6)	2.733 (6)	96 (4)
C4—H4···F6^i	0.88 (5)	2.58 (6)	3.282 (6)	137 (5)
C5—H5···Br2	0.86 (5)	2.68 (5)	3.323 (5)	133 (4)
C7—H7···F3^ii	0.91 (6)	2.48 (6)	3.370 (5)	166 (5)
C9—H9···F5^iii	0.91 (6)	2.57 (5)	3.466 (5)	166 (5)
C9—H9···F2^iv	0.91 (6)	2.58 (6)	3.211 (6)	127 (4)
C10—H10···F2^iv	0.97 (6)	2.62 (6)	3.255 (6)	123 (4)
C14—H14···Br1^v	0.87 (6)	2.95 (5)	3.744 (4)	152 (4)
C14—H14···Br2^v	0.87 (6)	2.96 (5)	3.505 (5)	122 (4)
C16—H16B···F7^vi	0.98 (6)	2.54 (6)	3.208 (6)	125 (4)
C16—H16B···F1^vii	0.98 (6)	2.49 (6)	3.167 (6)	126 (4)
Pt1—Br1···Br1^viii	2.43 (1)	3.69 (1)	6.091 (1)	168 (1)
C13—F2···F6^ix	1.35 (1)	2.91 (1)	4.148 (6)	151 (1)
C17—F6···F2^x	1.37 (1)	2.91 (1)	3.382 (4)	98 (1)

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