Cocrystals with tunable luminescence colour self-assembled by a predictable method

Organic light-emitting materials play an essential role in the field of luminescent materials because they are easily prepared and they have controllable luminescent properties. Here it is shown that intermolecular interactions and luminescent properties of cocrystals can be predicted using the molecular surface electrostatic potential of selected π-hole/σ-hole...π bonding donor haloperfluoro­benzenes and acceptor acenaphthene (AC). Single-crystal X-ray diffraction data reveal that actual bonding patterns in five cocrystals assembled from haloperfluoro­benzenes and AC are in accordance with predictable patterns of intermolecular interactions; that is π-hole...π bond is the major interaction in AC–octa­fluoro­naphthalene, AC–1,4-di­bromo­tetra­fluoro­benzene and AC–1,3,5-tri­bromo-2,4,6-tri­fluoro­benzene cocrystals, whereas σ-hole...π bond is the major interaction in AC–1,4-di­iodo­tetra­fluoro­benzene and AC–1,3,5-tri­fluoro-2,4,6-tri­iodo­benzene cocrystals. The luminescent properties of the cocrystals are affected by the bonding patterns between AC and haloperfluoro­benzenes; the π-hole...π bond leads to weak phospho­rescence, whereas the σ-hole...π bond results in weak delayed fluorescence and relatively strong phospho­rescence.

Computing details

Data collection: CrysAlis PRO 1.171.39.6a (Rigaku OD, 2015) for 20161215a, 20161201a, 20161228c; CrysAlis PRO 1.171.39.32a (Rigaku OD, 2017) for 20171220b, 20171220c. Cell refinement: CrysAlis PRO 1.171.39.6a (Rigaku OD, 2015) for 20161215a, 20161201a, 20161228c; CrysAlis PRO 1.171.39.32a (Rigaku OD, 2017) for 20171220b, 20171220c. Data reduction: CrysAlis PRO 1.171.39.6a (Rigaku OD, 2015) for 20161215a, 20161201a, 20161228c; CrysAlis PRO 1.171.39.32a (Rigaku OD, 2017) for 20171220b, 20171220c. Program(s) used to solve structure: SIR2004 (Burla et al., 2007) for 20161201a; ShelXT (Sheldrick, 2015) for 20161228c, 20171220b, 20171220c. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(20161215a)

Crystal data

C10F8·C12H10	F(000) = 428
Mr = 426.30	Dx = 1.729 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.2267 (10) Å	Cell parameters from 1105 reflections
b = 8.4607 (11) Å	θ = 3.9–28.5°
c = 13.509 (2) Å	µ = 0.16 mm^−1
β = 97.550 (15)°	T = 100 K
V = 818.8 (2) Å^3	Cube, colourless
Z = 2	0.35 × 0.3 × 0.3 mm

Data collection

SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer	2234 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1852 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 5.3127 pixels mm^-1	θmax = 25.3°, θmin = 3.7°
ω scans	h = −8→8
Absorption correction: multi-scan CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −7→10
Tmin = 0.574, Tmax = 1.000	l = −16→16
3239 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.0806P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.158	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.30 e Å^−3
2234 reflections	Δρmin = −0.45 e Å^−3
271 parameters	Absolute structure: Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: −1.6 (10)

Special details

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

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

	x	y	z	Uiso*/Ueq
F7	0.4581 (4)	0.3149 (5)	0.8676 (2)	0.0241 (9)
F1	0.6540 (4)	0.8867 (5)	0.9196 (2)	0.0239 (9)
F8	0.5402 (4)	0.6026 (5)	0.9439 (2)	0.0242 (8)
F3	0.7871 (4)	1.0455 (5)	0.6051 (2)	0.0238 (9)
F4	0.7051 (4)	0.7576 (4)	0.5284 (2)	0.0231 (8)
F2	0.7719 (4)	1.1062 (4)	0.7996 (2)	0.0229 (8)
F5	0.5886 (4)	0.4743 (5)	0.5526 (2)	0.0252 (9)
F6	0.4769 (5)	0.2536 (4)	0.6733 (2)	0.0237 (8)
C1	0.6645 (7)	0.8500 (8)	0.8236 (4)	0.0162 (14)
C9	0.5563 (7)	0.5765 (8)	0.8473 (4)	0.0176 (14)
C7	0.5234 (7)	0.3978 (8)	0.7101 (5)	0.0189 (14)
C6	0.5800 (8)	0.5099 (8)	0.6481 (4)	0.0177 (14)
C14	0.9707 (7)	−0.1035 (8)	0.2914 (5)	0.0211 (14)
H14	1.0006	−0.2062	0.3122	0.025*
C8	0.5126 (8)	0.4283 (8)	0.8087 (4)	0.0191 (14)
C3	0.7317 (7)	0.9306 (8)	0.6638 (4)	0.0173 (13)
C18	0.7823 (7)	0.4312 (8)	0.3514 (4)	0.0202 (14)
H18	0.7497	0.5118	0.3927	0.024*
C12	0.9283 (7)	0.0879 (8)	0.1588 (4)	0.0175 (13)
C10	0.6151 (7)	0.6963 (8)	0.7872 (4)	0.0153 (13)
C20	0.8348 (7)	0.3473 (8)	0.1875 (4)	0.0165 (13)
C11	0.8803 (7)	0.1958 (8)	0.2296 (4)	0.0174 (14)
C4	0.6899 (7)	0.7855 (8)	0.6244 (4)	0.0175 (14)
C19	0.7850 (7)	0.4643 (9)	0.2492 (4)	0.0216 (15)
H19	0.7532	0.5643	0.2240	0.026*
C5	0.6289 (7)	0.6634 (8)	0.6849 (4)	0.0156 (14)
C16	0.8764 (7)	0.1621 (8)	0.3304 (4)	0.0168 (13)
C21	0.8505 (8)	0.3394 (8)	0.0771 (4)	0.0237 (15)
H21A	0.9397	0.4166	0.0592	0.028*
H21B	0.7305	0.3592	0.0378	0.028*
C2	0.7199 (8)	0.9621 (8)	0.7626 (5)	0.0198 (14)
C15	0.9255 (8)	0.0039 (8)	0.3606 (4)	0.0212 (14)
H15	0.9268	−0.0261	0.4269	0.025*
C13	0.9736 (8)	−0.0646 (8)	0.1903 (5)	0.0231 (15)
H13	1.0055	−0.1401	0.1454	0.028*
C17	0.8258 (7)	0.2851 (8)	0.3927 (4)	0.0205 (14)
H17	0.8222	0.2674	0.4604	0.025*
C22	0.9180 (8)	0.1695 (8)	0.0596 (4)	0.0221 (14)
H22A	0.8308	0.1158	0.0100	0.027*
H22B	1.0397	0.1713	0.0366	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F7	0.0304 (17)	0.007 (2)	0.0355 (19)	−0.0007 (17)	0.0079 (15)	0.0061 (18)
F1	0.0354 (18)	0.011 (2)	0.0263 (17)	−0.0032 (17)	0.0086 (14)	−0.0042 (16)
F8	0.0319 (17)	0.015 (2)	0.0265 (17)	−0.0003 (17)	0.0083 (14)	−0.0003 (17)
F3	0.0303 (18)	0.0072 (19)	0.0351 (19)	−0.0045 (15)	0.0083 (15)	0.0072 (17)
F4	0.0340 (18)	0.012 (2)	0.0246 (16)	0.0016 (17)	0.0075 (14)	−0.0006 (17)
F2	0.0283 (17)	0.0058 (19)	0.0349 (18)	−0.0067 (16)	0.0054 (14)	−0.0039 (17)
F5	0.0376 (19)	0.012 (2)	0.0266 (18)	−0.0039 (17)	0.0068 (15)	−0.0044 (17)
F6	0.0338 (19)	0.0030 (18)	0.0338 (19)	−0.0013 (15)	0.0028 (15)	−0.0043 (17)
C1	0.017 (3)	0.009 (4)	0.023 (3)	0.005 (3)	0.003 (2)	0.001 (3)
C9	0.014 (3)	0.015 (4)	0.024 (3)	0.002 (3)	0.003 (2)	0.001 (3)
C7	0.013 (3)	0.009 (3)	0.033 (3)	0.003 (2)	−0.001 (2)	−0.005 (3)
C6	0.020 (3)	0.004 (3)	0.028 (3)	0.001 (3)	0.002 (2)	−0.002 (3)
C14	0.012 (3)	0.009 (3)	0.042 (3)	−0.006 (2)	0.001 (2)	0.005 (3)
C8	0.021 (3)	0.010 (4)	0.026 (3)	0.001 (3)	0.002 (2)	0.003 (3)
C3	0.017 (3)	0.007 (3)	0.029 (3)	0.005 (3)	0.009 (2)	0.003 (3)
C18	0.016 (3)	0.012 (4)	0.034 (3)	−0.001 (3)	0.008 (2)	−0.002 (3)
C12	0.014 (3)	0.011 (3)	0.028 (3)	−0.002 (3)	0.003 (2)	−0.008 (3)
C10	0.017 (3)	0.007 (3)	0.022 (3)	0.003 (3)	0.002 (2)	−0.002 (3)
C20	0.009 (2)	0.012 (4)	0.029 (3)	0.002 (2)	0.002 (2)	−0.001 (3)
C11	0.012 (3)	0.008 (3)	0.032 (3)	0.000 (3)	0.003 (2)	0.002 (3)
C4	0.015 (3)	0.009 (4)	0.030 (3)	0.003 (2)	0.006 (2)	0.003 (3)
C19	0.019 (3)	0.009 (4)	0.036 (3)	0.000 (3)	0.002 (2)	0.000 (3)
C5	0.011 (3)	0.006 (3)	0.030 (3)	−0.001 (2)	0.005 (2)	−0.002 (3)
C16	0.004 (2)	0.012 (3)	0.035 (3)	−0.001 (2)	0.005 (2)	0.002 (3)
C21	0.024 (3)	0.014 (4)	0.033 (3)	−0.001 (3)	0.004 (3)	0.002 (3)
C2	0.015 (3)	0.010 (4)	0.034 (3)	−0.002 (2)	0.002 (2)	−0.005 (3)
C15	0.026 (3)	0.011 (4)	0.026 (3)	−0.004 (3)	0.002 (2)	0.005 (3)
C13	0.026 (3)	0.007 (3)	0.036 (3)	0.001 (3)	0.001 (3)	−0.008 (3)
C17	0.023 (3)	0.012 (4)	0.029 (3)	−0.002 (3)	0.011 (2)	−0.001 (3)
C22	0.025 (3)	0.012 (4)	0.029 (3)	0.001 (3)	0.004 (2)	−0.005 (3)

Geometric parameters (Å, º)

F7—C8	1.339 (7)	C18—C17	1.375 (9)
F1—C1	1.346 (6)	C12—C11	1.399 (8)
F8—C9	1.344 (6)	C12—C13	1.385 (9)
F3—C3	1.348 (7)	C12—C22	1.501 (8)
F4—C4	1.337 (6)	C10—C5	1.426 (7)
F2—C2	1.352 (7)	C20—C11	1.423 (9)
F5—C6	1.334 (6)	C20—C19	1.372 (9)
F6—C7	1.344 (7)	C20—C21	1.512 (8)
C1—C10	1.419 (9)	C11—C16	1.394 (8)
C1—C2	1.351 (9)	C4—C5	1.423 (9)
C9—C8	1.378 (9)	C19—H19	0.9300
C9—C10	1.398 (9)	C16—C15	1.430 (10)
C7—C6	1.363 (9)	C16—C17	1.417 (9)
C7—C8	1.369 (8)	C21—H21A	0.9700
C6—C5	1.419 (9)	C21—H21B	0.9700
C14—H14	0.9300	C21—C22	1.546 (9)
C14—C15	1.374 (9)	C15—H15	0.9300
C14—C13	1.408 (8)	C13—H13	0.9300
C3—C4	1.356 (9)	C17—H17	0.9300
C3—C2	1.376 (8)	C22—H22A	0.9700
C18—H18	0.9300	C22—H22B	0.9700
C18—C19	1.411 (8)
F1—C1—C10	120.1 (5)	F4—C4—C3	119.9 (5)
F1—C1—C2	119.0 (6)	F4—C4—C5	120.0 (6)
C2—C1—C10	120.9 (5)	C3—C4—C5	120.1 (5)
F8—C9—C8	118.1 (5)	C18—C19—H19	120.3
F8—C9—C10	121.1 (6)	C20—C19—C18	119.3 (6)
C8—C9—C10	120.8 (5)	C20—C19—H19	120.3
F6—C7—C6	119.0 (5)	C6—C5—C10	118.2 (5)
F6—C7—C8	119.2 (6)	C6—C5—C4	123.0 (5)
C6—C7—C8	121.8 (6)	C4—C5—C10	118.8 (5)
F5—C6—C7	119.6 (6)	C11—C16—C15	115.7 (5)
F5—C6—C5	120.3 (5)	C11—C16—C17	118.0 (6)
C7—C6—C5	120.1 (5)	C17—C16—C15	126.3 (6)
C15—C14—H14	118.6	C20—C21—H21A	110.7
C15—C14—C13	122.8 (6)	C20—C21—H21B	110.7
C13—C14—H14	118.6	C20—C21—C22	105.0 (5)
F7—C8—C9	119.9 (5)	H21A—C21—H21B	108.8
F7—C8—C7	120.1 (6)	C22—C21—H21A	110.7
C7—C8—C9	120.0 (6)	C22—C21—H21B	110.7
F3—C3—C4	119.4 (5)	F2—C2—C3	119.0 (6)
F3—C3—C2	119.5 (6)	C1—C2—F2	119.9 (5)
C4—C3—C2	121.2 (6)	C1—C2—C3	121.1 (6)
C19—C18—H18	118.6	C14—C15—C16	119.8 (6)
C17—C18—H18	118.6	C14—C15—H15	120.1
C17—C18—C19	122.9 (6)	C16—C15—H15	120.1
C11—C12—C22	108.8 (6)	C14—C13—H13	120.6
C13—C12—C11	117.9 (5)	C12—C13—C14	118.9 (6)
C13—C12—C22	133.2 (6)	C12—C13—H13	120.6
C1—C10—C5	117.9 (5)	C18—C17—C16	118.8 (6)
C9—C10—C1	123.0 (5)	C18—C17—H17	120.6
C9—C10—C5	119.1 (5)	C16—C17—H17	120.6
C11—C20—C21	108.1 (5)	C12—C22—C21	105.7 (5)
C19—C20—C11	118.1 (5)	C12—C22—H22A	110.6
C19—C20—C21	133.7 (6)	C12—C22—H22B	110.6
C12—C11—C20	112.3 (5)	C21—C22—H22A	110.6
C16—C11—C12	124.9 (6)	C21—C22—H22B	110.6
C16—C11—C20	122.8 (5)	H22A—C22—H22B	108.7
F1—C1—C10—C9	−0.8 (8)	C10—C1—C2—C3	−0.5 (9)
F1—C1—C10—C5	−179.9 (4)	C10—C9—C8—F7	179.5 (4)
F1—C1—C2—F2	3.0 (8)	C10—C9—C8—C7	−1.1 (9)
F1—C1—C2—C3	−179.6 (5)	C20—C11—C16—C15	179.8 (5)
F8—C9—C8—F7	−0.8 (8)	C20—C11—C16—C17	−0.4 (7)
F8—C9—C8—C7	178.6 (5)	C20—C21—C22—C12	2.6 (5)
F8—C9—C10—C1	1.3 (8)	C11—C12—C13—C14	−0.5 (8)
F8—C9—C10—C5	−179.6 (4)	C11—C12—C22—C21	−2.1 (6)
F3—C3—C4—F4	0.4 (8)	C11—C20—C19—C18	0.6 (8)
F3—C3—C4—C5	−179.2 (4)	C11—C20—C21—C22	−2.3 (6)
F3—C3—C2—F2	−2.8 (8)	C11—C16—C15—C14	−0.6 (7)
F3—C3—C2—C1	179.8 (5)	C11—C16—C17—C18	0.3 (8)
F4—C4—C5—C6	−0.7 (8)	C4—C3—C2—F2	176.7 (5)
F4—C4—C5—C10	179.6 (4)	C4—C3—C2—C1	−0.7 (9)
F5—C6—C5—C10	179.2 (4)	C19—C18—C17—C16	0.3 (9)
F5—C6—C5—C4	−0.5 (8)	C19—C20—C11—C12	180.0 (4)
F6—C7—C6—F5	−0.2 (8)	C19—C20—C11—C16	−0.1 (8)
F6—C7—C6—C5	179.7 (4)	C19—C20—C21—C22	179.1 (6)
F6—C7—C8—F7	0.7 (8)	C21—C20—C11—C12	1.1 (6)
F6—C7—C8—C9	−178.7 (5)	C21—C20—C11—C16	−178.9 (4)
C1—C10—C5—C6	179.9 (5)	C21—C20—C19—C18	179.1 (5)
C1—C10—C5—C4	−0.4 (7)	C2—C1—C10—C9	−179.8 (5)
C9—C10—C5—C6	0.7 (7)	C2—C1—C10—C5	1.1 (8)
C9—C10—C5—C4	−179.6 (5)	C2—C3—C4—F4	−179.1 (5)
C7—C6—C5—C10	−0.7 (8)	C2—C3—C4—C5	1.3 (8)
C7—C6—C5—C4	179.7 (5)	C15—C14—C13—C12	−0.3 (8)
C6—C7—C8—F7	−179.4 (5)	C15—C16—C17—C18	−180.0 (5)
C6—C7—C8—C9	1.2 (9)	C13—C14—C15—C16	0.9 (8)
C8—C9—C10—C1	−179.0 (5)	C13—C12—C11—C20	−179.3 (5)
C8—C9—C10—C5	0.2 (8)	C13—C12—C11—C16	0.7 (8)
C8—C7—C6—F5	179.9 (5)	C13—C12—C22—C21	177.9 (6)
C8—C7—C6—C5	−0.3 (9)	C17—C18—C19—C20	−0.7 (8)
C3—C4—C5—C6	178.9 (5)	C17—C16—C15—C14	179.7 (5)
C3—C4—C5—C10	−0.7 (8)	C22—C12—C11—C20	0.7 (6)
C12—C11—C16—C15	−0.2 (7)	C22—C12—C11—C16	−179.3 (5)
C12—C11—C16—C17	179.6 (5)	C22—C12—C13—C14	179.6 (5)
C10—C1—C2—F2	−177.9 (5)

(20161201a)

Crystal data

Br2C6F4·C12H10	F(000) = 896
Mr = 462.08	Dx = 1.938 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.1989 (14) Å	Cell parameters from 1070 reflections
b = 14.436 (3) Å	θ = 3.7–25.0°
c = 12.167 (3) Å	µ = 5.16 mm^−1
β = 101.465 (16)°	T = 100 K
V = 1583.6 (6) Å^3	Block, colourless
Z = 4	0.4 × 0.35 × 0.3 mm

Data collection

SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer	3758 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1875 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.088
Detector resolution: 5.3127 pixels mm^-1	θmax = 29.8°, θmin = 3.3°
ω scans	h = −8→12
Absorption correction: multi-scan CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −17→19
Tmin = 0.185, Tmax = 1.000	l = −15→15
8312 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.108	H-atom parameters constrained
wR(F^2) = 0.255	w = 1/[σ^2(Fo^2) + (0.0809P)^2 + 2.854P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3758 reflections	Δρmax = 2.24 e Å^−3
217 parameters	Δρmin = −1.54 e Å^−3
12 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
Br1	0.15630 (12)	0.02632 (8)	0.39850 (10)	0.0288 (4)
Br2	0.12371 (11)	0.47822 (8)	0.36039 (10)	0.0289 (4)
F1	−0.0537 (6)	0.1608 (4)	0.4819 (5)	0.0263 (15)
F2	−0.0630 (6)	0.3456 (4)	0.4707 (5)	0.0296 (16)
F3	0.3355 (6)	0.3434 (4)	0.2783 (5)	0.0240 (15)
F4	0.3444 (6)	0.1594 (4)	0.2897 (5)	0.0259 (15)
C1	0.1464 (10)	0.1535 (8)	0.3879 (8)	0.020 (2)
C2	0.0431 (10)	0.2055 (7)	0.4312 (8)	0.018 (2)
C3	0.0372 (10)	0.3020 (7)	0.4248 (9)	0.017 (2)
C4	0.1334 (9)	0.3510 (8)	0.3736 (8)	0.017 (2)
C5	0.2370 (10)	0.3000 (8)	0.3282 (9)	0.022 (3)
C6	0.2418 (10)	0.2037 (7)	0.3355 (9)	0.019 (3)
C7	0.4321 (12)	0.4348 (8)	0.6097 (10)	0.032 (3)
H7A	0.3952	0.4676	0.5402	0.038*
H7B	0.5142	0.4695	0.6530	0.038*
C8	0.3072 (12)	0.4226 (8)	0.6774 (11)	0.037 (3)
H8A	0.3368	0.4485	0.7521	0.044*
H8B	0.2168	0.4529	0.6398	0.044*
C9	0.2850 (11)	0.3196 (9)	0.6827 (9)	0.030 (3)
C10	0.1840 (11)	0.2673 (9)	0.7267 (10)	0.032 (3)
H10	0.1121	0.2960	0.7589	0.039*
C11	0.1919 (12)	0.1702 (9)	0.7221 (10)	0.033 (3)
H11	0.1247	0.1349	0.7521	0.039*
C12	0.2977 (11)	0.1255 (8)	0.6735 (9)	0.025 (3)
H12	0.3021	0.0612	0.6727	0.030*
C13	0.3988 (10)	0.1787 (8)	0.6254 (8)	0.020 (2)
C14	0.3884 (10)	0.2760 (8)	0.6303 (9)	0.018 (2)
C15	0.4811 (11)	0.3385 (8)	0.5859 (10)	0.026 (3)
C16	0.5883 (11)	0.3018 (9)	0.5365 (10)	0.030 (3)
H16	0.6521	0.3411	0.5082	0.036*
C17	0.6042 (11)	0.2048 (9)	0.5276 (9)	0.032 (3)
H17	0.6769	0.1811	0.4921	0.038*
C18	0.5127 (12)	0.1447 (9)	0.5710 (9)	0.030 (3)
H18	0.5254	0.0811	0.5648	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0262 (6)	0.0220 (7)	0.0363 (8)	0.0000 (5)	0.0016 (5)	0.0011 (6)
Br2	0.0239 (6)	0.0248 (7)	0.0343 (8)	−0.0007 (5)	−0.0030 (5)	0.0006 (6)
F1	0.011 (3)	0.037 (4)	0.031 (4)	−0.003 (3)	0.003 (3)	0.008 (3)
F2	0.012 (3)	0.044 (4)	0.031 (4)	0.007 (3)	0.001 (3)	−0.009 (3)
F3	0.017 (3)	0.035 (4)	0.020 (4)	−0.007 (3)	0.006 (3)	0.008 (3)
F4	0.017 (3)	0.036 (4)	0.027 (4)	0.002 (3)	0.009 (3)	−0.007 (3)
C1	0.016 (5)	0.036 (7)	0.009 (6)	0.002 (5)	0.002 (4)	0.010 (5)
C2	0.007 (5)	0.032 (7)	0.011 (6)	0.001 (4)	−0.005 (4)	0.002 (5)
C3	0.015 (4)	0.022 (4)	0.014 (4)	0.004 (3)	0.000 (3)	−0.001 (4)
C4	0.011 (5)	0.030 (6)	0.011 (6)	−0.001 (4)	0.002 (4)	0.000 (5)
C5	0.014 (4)	0.025 (4)	0.024 (4)	0.000 (3)	−0.003 (3)	0.002 (4)
C6	0.005 (5)	0.028 (7)	0.021 (6)	0.005 (4)	−0.003 (4)	−0.005 (5)
C7	0.032 (6)	0.028 (7)	0.033 (8)	−0.004 (5)	0.001 (5)	0.005 (6)
C8	0.033 (6)	0.035 (8)	0.038 (8)	0.014 (6)	−0.001 (6)	−0.001 (6)
C9	0.015 (6)	0.054 (9)	0.017 (7)	0.003 (5)	−0.005 (5)	0.000 (6)
C10	0.015 (5)	0.065 (10)	0.016 (7)	0.000 (6)	0.002 (5)	0.000 (7)
C11	0.024 (6)	0.054 (9)	0.022 (7)	−0.001 (6)	0.008 (5)	0.004 (6)
C12	0.022 (6)	0.029 (7)	0.020 (7)	−0.001 (5)	−0.008 (5)	−0.001 (5)
C13	0.015 (5)	0.034 (7)	0.009 (6)	−0.006 (5)	0.000 (4)	−0.004 (5)
C14	0.009 (4)	0.028 (6)	0.015 (6)	0.004 (4)	−0.004 (4)	−0.002 (5)
C15	0.021 (6)	0.036 (7)	0.021 (7)	0.002 (5)	0.000 (5)	0.000 (6)
C16	0.013 (5)	0.044 (8)	0.030 (7)	−0.009 (5)	−0.003 (5)	0.007 (6)
C17	0.013 (5)	0.058 (9)	0.025 (7)	0.016 (6)	0.006 (5)	−0.001 (6)
C18	0.031 (6)	0.037 (8)	0.022 (7)	0.014 (6)	0.001 (5)	−0.006 (6)

Geometric parameters (Å, º)

Br1—C1	1.842 (12)	C8—C9	1.505 (16)
Br2—C4	1.844 (11)	C9—C10	1.384 (16)
F1—C2	1.345 (11)	C9—C14	1.396 (14)
F2—C3	1.328 (11)	C10—H10	0.9300
F3—C5	1.343 (12)	C10—C11	1.406 (16)
F4—C6	1.349 (11)	C11—H11	0.9300
C1—C2	1.393 (14)	C11—C12	1.394 (15)
C1—C6	1.387 (14)	C12—H12	0.9300
C2—C3	1.396 (14)	C12—C13	1.419 (14)
C3—C4	1.375 (13)	C13—C14	1.411 (15)
C4—C5	1.401 (14)	C13—C18	1.432 (14)
C5—C6	1.393 (15)	C14—C15	1.420 (15)
C7—H7A	0.9700	C15—C16	1.359 (15)
C7—H7B	0.9700	C16—H16	0.9300
C7—C8	1.550 (16)	C16—C17	1.415 (17)
C7—C15	1.507 (16)	C17—H17	0.9300
C8—H8A	0.9700	C17—C18	1.385 (16)
C8—H8B	0.9700	C18—H18	0.9300
C2—C1—Br1	122.6 (8)	C10—C9—C8	131.5 (11)
C6—C1—Br1	121.7 (8)	C10—C9—C14	120.1 (12)
C6—C1—C2	115.7 (10)	C14—C9—C8	108.3 (10)
F1—C2—C1	118.6 (9)	C9—C10—H10	120.5
F1—C2—C3	118.8 (9)	C9—C10—C11	119.0 (11)
C1—C2—C3	122.6 (9)	C11—C10—H10	120.5
F2—C3—C2	118.2 (9)	C10—C11—H11	119.2
F2—C3—C4	120.7 (9)	C12—C11—C10	121.6 (11)
C4—C3—C2	121.1 (9)	C12—C11—H11	119.2
C3—C4—Br2	121.8 (8)	C11—C12—H12	120.1
C3—C4—C5	117.2 (10)	C11—C12—C13	119.7 (11)
C5—C4—Br2	121.0 (8)	C13—C12—H12	120.1
F3—C5—C4	120.4 (9)	C12—C13—C18	127.2 (11)
F3—C5—C6	118.6 (9)	C14—C13—C12	117.7 (9)
C6—C5—C4	121.0 (10)	C14—C13—C18	115.1 (10)
F4—C6—C1	120.1 (10)	C9—C14—C13	121.8 (10)
F4—C6—C5	117.6 (9)	C9—C14—C15	113.8 (11)
C1—C6—C5	122.3 (9)	C13—C14—C15	124.4 (9)
H7A—C7—H7B	108.7	C14—C15—C7	106.7 (9)
C8—C7—H7A	110.5	C16—C15—C7	135.7 (11)
C8—C7—H7B	110.5	C16—C15—C14	117.6 (11)
C15—C7—H7A	110.5	C15—C16—H16	119.5
C15—C7—H7B	110.5	C15—C16—C17	121.0 (10)
C15—C7—C8	106.3 (9)	C17—C16—H16	119.5
C7—C8—H8A	110.8	C16—C17—H17	119.6
C7—C8—H8B	110.8	C18—C17—C16	120.7 (10)
H8A—C8—H8B	108.9	C18—C17—H17	119.6
C9—C8—C7	104.8 (9)	C13—C18—H18	119.4
C9—C8—H8A	110.8	C17—C18—C13	121.1 (11)
C9—C8—H8B	110.8	C17—C18—H18	119.4
Br1—C1—C2—F1	−0.5 (13)	C8—C7—C15—C14	2.7 (12)
Br1—C1—C2—C3	178.9 (7)	C8—C7—C15—C16	−176.0 (13)
Br1—C1—C6—F4	0.7 (13)	C8—C9—C10—C11	−178.4 (11)
Br1—C1—C6—C5	−179.1 (7)	C8—C9—C14—C13	177.7 (9)
Br2—C4—C5—F3	2.8 (13)	C8—C9—C14—C15	−1.1 (13)
Br2—C4—C5—C6	−178.3 (7)	C9—C10—C11—C12	−0.6 (17)
F1—C2—C3—F2	1.0 (13)	C9—C14—C15—C7	−1.1 (12)
F1—C2—C3—C4	−179.8 (9)	C9—C14—C15—C16	178.0 (10)
F2—C3—C4—Br2	−2.7 (14)	C10—C9—C14—C13	−3.3 (16)
F2—C3—C4—C5	179.3 (8)	C10—C9—C14—C15	177.9 (10)
F3—C5—C6—F4	−1.3 (13)	C10—C11—C12—C13	−1.3 (17)
F3—C5—C6—C1	178.5 (9)	C11—C12—C13—C14	0.8 (15)
C1—C2—C3—F2	−178.5 (9)	C11—C12—C13—C18	−179.1 (10)
C1—C2—C3—C4	0.8 (15)	C12—C13—C14—C9	1.4 (15)
C2—C1—C6—F4	−179.1 (8)	C12—C13—C14—C15	−179.9 (9)
C2—C1—C6—C5	1.1 (14)	C12—C13—C18—C17	−179.9 (10)
C2—C3—C4—Br2	178.1 (7)	C13—C14—C15—C7	−179.9 (9)
C2—C3—C4—C5	0.1 (14)	C13—C14—C15—C16	−0.8 (16)
C3—C4—C5—F3	−179.1 (9)	C14—C9—C10—C11	2.8 (16)
C3—C4—C5—C6	−0.2 (14)	C14—C13—C18—C17	0.1 (15)
C4—C5—C6—F4	179.8 (8)	C14—C15—C16—C17	1.4 (16)
C4—C5—C6—C1	−0.4 (15)	C15—C7—C8—C9	−3.3 (12)
C6—C1—C2—F1	179.3 (8)	C15—C16—C17—C18	−1.3 (16)
C6—C1—C2—C3	−1.3 (14)	C16—C17—C18—C13	0.5 (16)
C7—C8—C9—C10	−176.1 (12)	C18—C13—C14—C9	−178.6 (9)
C7—C8—C9—C14	2.7 (12)	C18—C13—C14—C15	0.1 (15)
C7—C15—C16—C17	−179.9 (11)

(20161228c)

Crystal data

C6F4I2·C12H10	Z = 1
Mr = 556.06	F(000) = 260
Triclinic, P1	Dx = 2.233 Mg m^−3
a = 5.3366 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.4653 (4) Å	Cell parameters from 2155 reflections
c = 12.1051 (6) Å	θ = 4.3–29.5°
α = 96.549 (4)°	µ = 3.84 mm^−1
β = 92.853 (4)°	T = 100 K
γ = 93.382 (4)°	Block, colourless
V = 413.53 (4) Å^3	0.5 × 0.4 × 0.3 mm

Data collection

SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer	1902 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1782 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
Detector resolution: 5.3127 pixels mm^-1	θmax = 29.6°, θmin = 3.8°
ω scans	h = −6→6
Absorption correction: multi-scan CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −8→8
Tmin = 0.675, Tmax = 1.000	l = −15→11
2982 measured reflections

Refinement

Refinement on F^2	90 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0322P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1902 reflections	Δρmax = 1.10 e Å^−3
163 parameters	Δρmin = −1.76 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.8267 (8)	0.1019 (7)	0.0694 (3)	0.0113 (9)
C2	0.9292 (8)	−0.0816 (7)	0.0946 (4)	0.0118 (9)
C3	1.0986 (8)	−0.1804 (7)	0.0276 (4)	0.0122 (8)
C4	0.435 (2)	0.433 (2)	0.4995 (10)	0.013 (3)	0.5
C5	0.241 (3)	0.398 (3)	0.4179 (14)	0.019 (4)	0.5
C6	0.204 (4)	0.527 (3)	0.3367 (17)	0.016 (6)	0.5
H6	0.0694	0.5088	0.2841	0.019*	0.5
C7	0.418 (3)	0.710 (2)	0.3425 (12)	0.005 (3)	0.5
H7	0.4282	0.7996	0.2876	0.006*	0.5
C8	0.566 (3)	0.727 (3)	0.4220 (16)	0.015 (5)	0.5
H8	0.6724	0.8474	0.4281	0.018*	0.5
C9	0.610 (2)	0.599 (2)	0.5089 (10)	0.008 (3)	0.5
C10	0.796 (2)	0.607 (2)	0.5981 (11)	0.002 (3)	0.5
H10	0.9261	0.7105	0.6083	0.003*	0.5
C11	0.773 (4)	0.455 (3)	0.6688 (14)	0.007 (4)	0.5
H11	0.8854	0.4703	0.7310	0.009*	0.5
C12	0.621 (3)	0.300 (3)	0.6590 (16)	0.020 (5)	0.5
H12	0.6431	0.1987	0.7066	0.023*	0.5
C13	0.397 (3)	0.268 (3)	0.5717 (13)	0.007 (4)	0.5
C14	0.1997 (15)	0.1241 (14)	0.5384 (7)	0.0108 (17)	0.5
H14A	0.0795	0.1215	0.5958	0.013*	0.5
H14B	0.2595	−0.0144	0.5225	0.013*	0.5
C15	0.0780 (17)	0.1973 (15)	0.4314 (8)	0.0151 (18)	0.5
H15A	0.0864	0.0931	0.3676	0.018*	0.5
H15B	−0.0962	0.2270	0.4410	0.018*	0.5
F1	0.8661 (5)	−0.1640 (4)	0.1870 (2)	0.0205 (6)
F2	1.1945 (5)	−0.3539 (4)	0.0577 (2)	0.0200 (6)
I1	0.57944 (5)	0.25500 (4)	0.17238 (2)	0.01397 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0107 (11)	0.0118 (12)	0.0112 (12)	0.0012 (9)	0.0006 (9)	0.0005 (9)
C2	0.0122 (11)	0.0121 (12)	0.0109 (11)	0.0005 (9)	0.0009 (9)	0.0011 (9)
C3	0.0128 (11)	0.0109 (12)	0.0128 (12)	0.0019 (9)	−0.0007 (9)	0.0016 (9)
C4	0.013 (3)	0.013 (3)	0.013 (3)	0.0009 (10)	0.0007 (10)	0.0013 (11)
C5	0.019 (4)	0.019 (4)	0.019 (4)	0.0017 (11)	0.0013 (11)	0.0019 (11)
C6	0.016 (6)	0.016 (6)	0.016 (6)	0.0009 (11)	0.0011 (11)	0.0015 (12)
C7	0.005 (4)	0.005 (4)	0.005 (4)	0.0000 (10)	0.0007 (10)	0.0008 (11)
C8	0.015 (5)	0.015 (5)	0.015 (5)	0.0011 (11)	0.0009 (11)	0.0015 (12)
C9	0.008 (3)	0.008 (3)	0.008 (3)	0.0005 (10)	0.0009 (10)	0.0008 (10)
C10	0.002 (3)	0.002 (3)	0.002 (3)	0.0005 (10)	−0.0003 (10)	−0.0006 (10)
C11	0.007 (5)	0.007 (5)	0.007 (5)	0.0004 (11)	0.0009 (10)	0.0006 (11)
C12	0.020 (5)	0.020 (5)	0.019 (5)	0.0016 (11)	0.0010 (11)	0.0024 (12)
C13	0.007 (4)	0.006 (4)	0.007 (4)	0.0006 (11)	0.0001 (10)	0.0006 (11)
C14	0.0110 (18)	0.0107 (19)	0.0108 (18)	0.0001 (10)	0.0010 (10)	0.0019 (10)
C15	0.015 (2)	0.015 (2)	0.015 (2)	0.0007 (10)	0.0008 (10)	0.0015 (10)
F1	0.0313 (16)	0.0195 (15)	0.0130 (14)	0.0070 (12)	0.0049 (11)	0.0077 (12)
F2	0.0286 (15)	0.0131 (14)	0.0203 (15)	0.0107 (12)	0.0026 (11)	0.0050 (11)
I1	0.01473 (17)	0.01438 (18)	0.01160 (17)	0.00283 (12)	0.00023 (10)	−0.00434 (12)

Geometric parameters (Å, º)

C1—C2	1.394 (6)	C8—H8	0.9300
C1—C3^i	1.397 (6)	C8—C9	1.43 (2)
C1—I1	2.077 (4)	C9—C10	1.422 (16)
C2—C3	1.381 (6)	C10—H10	0.9300
C2—F1	1.342 (5)	C10—C11	1.38 (2)
C3—C1^i	1.397 (6)	C11—H11	0.9300
C3—F2	1.340 (5)	C11—C12	1.24 (3)
C4—C5	1.384 (19)	C12—H12	0.9300
C4—C9	1.372 (16)	C12—C13	1.54 (2)
C4—C13	1.47 (2)	C13—C14	1.379 (18)
C5—C6	1.37 (3)	C14—H14A	0.9700
C5—C15	1.549 (18)	C14—H14B	0.9700
C6—H6	0.9300	C14—C15	1.554 (12)
C6—C7	1.59 (3)	C15—H15A	0.9700
C7—H7	0.9300	C15—H15B	0.9700
C7—C8	1.21 (2)
C2—C1—C3^i	116.9 (4)	C10—C9—C8	133.8 (13)
C2—C1—I1	121.6 (3)	C9—C10—H10	121.4
C3^i—C1—I1	121.4 (3)	C11—C10—C9	117.1 (13)
C3—C2—C1	121.6 (4)	C11—C10—H10	121.4
F1—C2—C1	119.7 (4)	C10—C11—H11	116.2
F1—C2—C3	118.6 (4)	C12—C11—C10	127.5 (18)
C2—C3—C1^i	121.5 (4)	C12—C11—H11	116.2
F2—C3—C1^i	119.8 (4)	C11—C12—H12	118.5
F2—C3—C2	118.7 (4)	C11—C12—C13	123.1 (18)
C5—C4—C13	105.6 (13)	C13—C12—H12	118.4
C9—C4—C5	124.4 (10)	C4—C13—C12	105.7 (13)
C9—C4—C13	129.9 (10)	C14—C13—C4	115.2 (13)
C4—C5—C15	110.9 (13)	C14—C13—C12	138.7 (15)
C6—C5—C4	123.1 (16)	C13—C14—H14A	110.7
C6—C5—C15	125.9 (15)	C13—C14—H14B	110.7
C5—C6—H6	123.7	C13—C14—C15	105.3 (9)
C5—C6—C7	112.6 (17)	H14A—C14—H14B	108.8
C7—C6—H6	123.7	C15—C14—H14A	110.7
C6—C7—H7	121.9	C15—C14—H14B	110.7
C8—C7—C6	116.2 (17)	C5—C15—C14	102.9 (8)
C8—C7—H7	121.9	C5—C15—H15A	111.2
C7—C8—H8	113.6	C5—C15—H15B	111.2
C7—C8—C9	132.9 (18)	C14—C15—H15A	111.2
C9—C8—H8	113.6	C14—C15—H15B	111.2
C4—C9—C8	110.3 (11)	H15A—C15—H15B	109.1
C4—C9—C10	115.9 (8)
C1—C2—C3—C1^i	−0.6 (7)	C9—C4—C5—C15	179.9 (8)
C1—C2—C3—F2	178.6 (4)	C9—C4—C13—C12	−6.4 (17)
C3^i—C1—C2—C3	0.6 (7)	C9—C4—C13—C14	179.6 (9)
C3^i—C1—C2—F1	179.6 (4)	C9—C10—C11—C12	6 (3)
C4—C5—C6—C7	4 (2)	C10—C11—C12—C13	−10 (3)
C4—C5—C15—C14	2.6 (14)	C11—C12—C13—C4	8 (2)
C4—C9—C10—C11	−3.1 (15)	C11—C12—C13—C14	−179.7 (18)
C4—C13—C14—C15	−1.4 (15)	C12—C13—C14—C15	−172.6 (18)
C5—C4—C9—C8	−0.7 (14)	C13—C4—C5—C6	177.0 (16)
C5—C4—C9—C10	−179.6 (17)	C13—C4—C5—C15	−3.3 (16)
C5—C4—C13—C12	177.0 (13)	C13—C4—C9—C8	−176.7 (19)
C5—C4—C13—C14	3.0 (17)	C13—C4—C9—C10	4.4 (14)
C5—C6—C7—C8	−8 (2)	C13—C14—C15—C5	−0.7 (12)
C6—C5—C15—C14	−177.7 (16)	C15—C5—C6—C7	−175.9 (13)
C6—C7—C8—C9	9 (3)	F1—C2—C3—C1^i	−179.6 (4)
C7—C8—C9—C4	−5 (3)	F1—C2—C3—F2	−0.4 (6)
C7—C8—C9—C10	174.0 (18)	I1—C1—C2—C3	−178.3 (3)
C8—C9—C10—C11	178.4 (16)	I1—C1—C2—F1	0.7 (5)
C9—C4—C5—C6	0 (2)

Symmetry code: (i) −x+2, −y, −z.

(20171220b)

Crystal data

3(Br3C6F3)·3(C12H10)	Dx = 2.112 Mg m^−3
Mr = 1568.94	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P321	Cell parameters from 2663 reflections
a = 14.4575 (7) Å	θ = 4.1–26.3°
c = 6.8147 (3) Å	µ = 7.39 mm^−1
V = 1233.57 (13) Å^3	T = 100 K
Z = 1.0	Block, clear light white
F(000) = 750	0.25 × 0.25 × 0.2 mm

Data collection

SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer	2098 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	1933 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.063
Detector resolution: 5.3127 pixels mm^-1	θmax = 29.7°, θmin = 3.4°
ω scans	h = −19→18
Absorption correction: multi-scan CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −13→19
Tmin = 0.904, Tmax = 1.000	l = −9→8
7700 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0282P)^2 + 4.0988P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 1.38 e Å^−3
2098 reflections	Δρmin = −0.67 e Å^−3
226 parameters	Absolute structure: Refined as an inversion twin.
410 restraints	Absolute structure parameter: 0.35 (4)
Primary atom site location: dual

Special details

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

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.0000	0.77396 (8)	0.5000	0.0158 (3)
Br2	0.42684 (7)	0.12482 (8)	0.66868 (14)	0.0222 (3)
C1	0.0000	0.9024 (8)	0.5000	0.011 (2)
C2	0.0943 (7)	1.0000	0.5000	0.009 (2)
C3	0.5645 (7)	0.2446 (7)	0.6724 (11)	0.0133 (18)
C4	0.6532 (7)	0.2329 (7)	0.6720 (12)	0.0145 (18)
C5	0.480 (2)	0.295 (2)	0.167 (5)	0.020 (5)	0.3333
H5A	0.4362	0.2722	0.0503	0.024*	0.3333
H5B	0.4340	0.2692	0.2810	0.024*	0.3333
C6	0.548 (2)	0.416 (2)	0.173 (5)	0.016 (5)	0.3333
H6A	0.5335	0.4441	0.2898	0.019*	0.3333
H6B	0.5351	0.4472	0.0582	0.019*	0.3333
C7	0.6656 (16)	0.4382 (18)	0.174 (3)	0.008 (4)	0.3333
C8	0.7662 (18)	0.5291 (16)	0.179 (4)	0.015 (5)	0.3333
H8	0.7727	0.5964	0.1807	0.018*	0.3333
C9	0.8571 (16)	0.5194 (16)	0.183 (4)	0.019 (6)	0.3333
H9	0.9244	0.5802	0.1871	0.022*	0.3333
C10	0.8474 (13)	0.4187 (17)	0.181 (3)	0.015 (5)	0.3333
H10	0.9082	0.4122	0.1840	0.018*	0.3333
C11	0.7468 (14)	0.3279 (16)	0.1758 (18)	0.015 (5)	0.3333
C12	0.6559 (13)	0.3376 (17)	0.1720 (11)	0.008 (3)	0.3333
C13	0.5553 (13)	0.2467 (19)	0.166 (3)	0.015 (5)	0.3333
C14	0.5456 (16)	0.1461 (17)	0.164 (4)	0.023 (6)	0.3333
H14	0.4783	0.0853	0.1607	0.028*	0.3333
C15	0.6365 (19)	0.1363 (16)	0.168 (4)	0.028 (6)	0.3333
H15	0.6300	0.0690	0.1671	0.033*	0.3333
C16	0.7371 (17)	0.2272 (17)	0.174 (4)	0.024 (6)	0.3333
H16	0.7979	0.2207	0.1765	0.029*	0.3333
C17	−0.189 (7)	−0.136 (4)	0.995 (18)	0.007 (7)	0.1667
H17A	−0.2351	−0.1552	1.1092	0.009*	0.1667
H17B	−0.2332	−0.1574	0.8774	0.009*	0.1667
C18	−0.119 (4)	−0.188 (6)	1.002 (18)	0.007 (7)	0.1667
H18A	−0.1326	−0.2326	0.8878	0.008*	0.1667
H18B	−0.1362	−0.2323	1.1182	0.008*	0.1667
C19	0.001 (4)	−0.100 (3)	1.007 (13)	0.006 (5)	0.1667
C20	0.100 (5)	−0.093 (4)	1.018 (10)	0.005 (6)	0.1667
H20	0.1049	−0.1546	1.0211	0.006*	0.1667
C21	0.192 (4)	0.007 (4)	1.023 (7)	0.004 (7)	0.1667
H21	0.2587	0.0117	1.0303	0.004*	0.1667
C22	0.185 (3)	0.099 (3)	1.018 (8)	0.011 (7)	0.1667
H22	0.2465	0.1657	1.0221	0.013*	0.1667
C23	0.085 (3)	0.092 (3)	1.008 (6)	0.009 (6)	0.1667
C24	−0.007 (3)	−0.008 (3)	1.003 (8)	0.008 (4)	0.1667
C25	−0.106 (3)	−0.015 (4)	0.992 (12)	0.007 (6)	0.1667
C26	−0.114 (2)	0.077 (5)	0.987 (9)	0.007 (6)	0.1667
H26	−0.1802	0.0720	0.9803	0.008*	0.1667
C27	−0.021 (2)	0.177 (4)	0.993 (8)	0.005 (7)	0.1667
H27	−0.0263	0.2383	0.9894	0.007*	0.1667
C28	0.078 (2)	0.184 (3)	1.003 (9)	0.009 (7)	0.1667
H28	0.1397	0.2505	1.0068	0.010*	0.1667
F1	0.1883 (5)	1.0000	0.5000	0.0125 (14)
F2	0.6413 (5)	0.1354 (4)	0.6709 (8)	0.0219 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0207 (7)	0.0117 (4)	0.0180 (6)	0.0103 (3)	−0.0003 (5)	−0.0001 (3)
Br2	0.0140 (5)	0.0183 (5)	0.0254 (5)	0.0014 (4)	−0.0015 (4)	−0.0028 (4)
C1	0.013 (5)	0.012 (4)	0.010 (5)	0.007 (3)	0.000 (4)	0.000 (2)
C2	0.007 (4)	0.013 (5)	0.009 (5)	0.007 (3)	0.001 (2)	0.001 (4)
C3	0.012 (4)	0.013 (4)	0.008 (4)	0.001 (3)	−0.002 (3)	−0.001 (3)
C4	0.020 (4)	0.013 (5)	0.013 (4)	0.010 (4)	0.001 (3)	−0.002 (4)
C5	0.014 (8)	0.018 (8)	0.021 (8)	0.002 (6)	0.000 (7)	−0.001 (7)
C6	0.016 (8)	0.012 (8)	0.018 (8)	0.006 (6)	−0.001 (7)	0.004 (7)
C7	0.008 (4)	0.008 (4)	0.008 (4)	0.004 (2)	0.0000 (14)	0.0002 (14)
C8	0.022 (8)	0.006 (7)	0.008 (8)	0.001 (6)	0.000 (7)	−0.004 (7)
C9	0.027 (9)	0.014 (8)	0.011 (9)	0.007 (7)	−0.006 (8)	−0.004 (7)
C10	0.014 (8)	0.022 (9)	0.011 (8)	0.011 (6)	0.002 (7)	−0.002 (8)
C11	0.015 (7)	0.024 (7)	0.007 (7)	0.010 (6)	0.002 (6)	−0.003 (7)
C12	0.008 (4)	0.008 (4)	0.007 (3)	0.004 (2)	−0.0002 (14)	0.0001 (14)
C13	0.010 (7)	0.017 (7)	0.008 (7)	−0.002 (6)	−0.004 (6)	−0.001 (6)
C14	0.017 (8)	0.024 (8)	0.014 (8)	−0.001 (7)	−0.004 (8)	0.000 (8)
C15	0.019 (9)	0.040 (9)	0.018 (9)	0.010 (7)	0.000 (8)	0.003 (8)
C16	0.025 (9)	0.030 (9)	0.021 (9)	0.016 (7)	0.002 (8)	−0.002 (8)
C17	0.007 (9)	0.007 (9)	0.007 (9)	0.004 (7)	0.002 (8)	0.001 (9)
C18	0.006 (9)	0.006 (9)	0.008 (9)	0.003 (7)	−0.001 (9)	0.001 (9)
C19	0.007 (8)	0.006 (8)	0.006 (8)	0.003 (6)	0.001 (8)	0.001 (8)
C20	0.005 (7)	0.005 (7)	0.005 (7)	0.003 (3)	−0.0001 (14)	0.0000 (14)
C21	0.004 (7)	0.004 (7)	0.004 (7)	0.002 (3)	−0.0001 (14)	0.0001 (14)
C22	0.009 (9)	0.009 (9)	0.011 (10)	0.002 (7)	0.002 (8)	−0.004 (8)
C23	0.010 (8)	0.009 (8)	0.009 (8)	0.005 (6)	0.001 (8)	0.000 (8)
C24	0.009 (7)	0.009 (7)	0.005 (6)	0.002 (6)	0.000 (8)	0.000 (8)
C25	0.007 (8)	0.007 (8)	0.006 (8)	0.003 (6)	0.000 (8)	0.000 (8)
C26	0.007 (6)	0.007 (6)	0.007 (6)	0.003 (3)	−0.0001 (14)	0.0000 (14)
C27	0.006 (7)	0.005 (7)	0.005 (7)	0.003 (4)	−0.0001 (14)	0.0001 (14)
C28	0.009 (9)	0.007 (9)	0.009 (10)	0.003 (7)	0.003 (9)	−0.001 (8)
F1	0.011 (2)	0.012 (4)	0.015 (3)	0.0061 (18)	−0.0013 (14)	−0.003 (3)
F2	0.029 (3)	0.013 (3)	0.030 (3)	0.015 (2)	−0.001 (3)	−0.003 (2)

Geometric parameters (Å, º)

Br1—C1	1.857 (12)	C14—H14	0.9300
Br2—C3	1.875 (8)	C14—C15	1.3900
C1—C2	1.388 (8)	C15—H15	0.9300
C1—C2^i	1.388 (8)	C15—C16	1.3900
C2—C1^ii	1.388 (8)	C16—H16	0.9300
C2—F1	1.360 (13)	C17—H17A	0.9700
C3—C4^iii	1.380 (12)	C17—H17B	0.9700
C3—C4	1.375 (12)	C17—C18	1.533 (14)
C4—C3^iv	1.380 (12)	C17—C25	1.55 (3)
C4—F2	1.333 (10)	C18—H18A	0.9700
C5—H5A	0.9700	C18—H18B	0.9700
C5—H5B	0.9700	C18—C19	1.55 (3)
C5—C6	1.522 (14)	C19—C20	1.3900
C5—C13	1.55 (2)	C19—C24	1.3900
C6—H6A	0.9700	C20—H20	0.9300
C6—H6B	0.9700	C20—C21	1.3900
C6—C7	1.56 (2)	C21—H21	0.9300
C7—C8	1.3900	C21—C22	1.3900
C7—C12	1.3900	C22—H22	0.9300
C8—H8	0.9300	C22—C23	1.3900
C8—C9	1.3900	C23—C24	1.3900
C9—H9	0.9300	C23—C28	1.3900
C9—C10	1.3900	C24—C25	1.3900
C10—H10	0.9300	C25—C26	1.3900
C10—C11	1.3900	C26—H26	0.9300
C11—C12	1.3900	C26—C27	1.3900
C11—C16	1.3900	C27—H27	0.9300
C12—C13	1.3900	C27—C28	1.3900
C13—C14	1.3900	C28—H28	0.9300
C2—C1—Br1	121.7 (6)	C14—C15—H15	120.0
C2^i—C1—Br1	121.7 (6)	C14—C15—C16	120.0
C2—C1—C2^i	116.5 (12)	C16—C15—H15	120.0
C1^ii—C2—C1	123.5 (12)	C11—C16—H16	120.0
F1—C2—C1^ii	118.3 (6)	C15—C16—C11	120.0
F1—C2—C1	118.3 (6)	C15—C16—H16	120.0
C4^iii—C3—Br2	121.0 (7)	H17A—C17—H17B	109.1
C4—C3—Br2	120.8 (7)	C18—C17—H17A	111.2
C4—C3—C4^iii	118.2 (9)	C18—C17—H17B	111.2
C3—C4—C3^iv	121.8 (9)	C18—C17—C25	103 (8)
F2—C4—C3^iv	118.5 (8)	C25—C17—H17A	111.2
F2—C4—C3	119.6 (8)	C25—C17—H17B	111.2
H5A—C5—H5B	108.3	C17—C18—H18A	109.6
C6—C5—H5A	109.9	C17—C18—H18B	109.6
C6—C5—H5B	109.9	C17—C18—C19	110 (8)
C6—C5—C13	109 (2)	H18A—C18—H18B	108.1
C13—C5—H5A	109.9	C19—C18—H18A	109.6
C13—C5—H5B	109.9	C19—C18—H18B	109.6
C5—C6—H6A	110.9	C20—C19—C18	139 (5)
C5—C6—H6B	110.9	C20—C19—C24	120.0
C5—C6—C7	104 (2)	C24—C19—C18	101 (5)
H6A—C6—H6B	108.9	C19—C20—H20	120.0
C7—C6—H6A	110.9	C21—C20—C19	120.0
C7—C6—H6B	110.9	C21—C20—H20	120.0
C8—C7—C6	135.4 (12)	C20—C21—H21	120.0
C8—C7—C12	120.0	C20—C21—C22	120.0
C12—C7—C6	104.5 (12)	C22—C21—H21	120.0
C7—C8—H8	120.0	C21—C22—H22	120.0
C7—C8—C9	120.0	C23—C22—C21	120.0
C9—C8—H8	120.0	C23—C22—H22	120.0
C8—C9—H9	120.0	C22—C23—C24	120.0
C10—C9—C8	120.0	C22—C23—C28	120.0
C10—C9—H9	120.0	C24—C23—C28	120.0
C9—C10—H10	120.0	C23—C24—C19	120.0
C9—C10—C11	120.0	C25—C24—C19	120.00 (6)
C11—C10—H10	120.0	C25—C24—C23	120.0
C10—C11—C16	120.0	C24—C25—C17	106 (5)
C12—C11—C10	120.0	C24—C25—C26	120.0
C12—C11—C16	120.0	C26—C25—C17	134 (5)
C11—C12—C7	120.0	C25—C26—H26	120.0
C13—C12—C7	120.0	C25—C26—C27	120.0
C13—C12—C11	120.0	C27—C26—H26	120.0
C12—C13—C5	102.3 (12)	C26—C27—H27	120.0
C12—C13—C14	120.0	C28—C27—C26	120.0
C14—C13—C5	137.7 (12)	C28—C27—H27	120.0
C13—C14—H14	120.0	C23—C28—H28	120.0
C15—C14—C13	120.0	C27—C28—C23	120.0
C15—C14—H14	120.0	C27—C28—H28	120.0

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

(20171220c)

Crystal data

2(C6F3I3)·C12H10	F(000) = 4208
Mr = 1173.72	Dx = 2.713 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 14.2199 (4) Å	Cell parameters from 13221 reflections
b = 45.6676 (11) Å	θ = 3.6–29.4°
c = 8.9289 (3) Å	µ = 6.54 mm^−1
β = 97.688 (2)°	T = 100 K
V = 5746.2 (3) Å^3	Block, clear light white
Z = 8	0.25 × 0.2 × 0.1 mm

Data collection

SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer	10741 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	9570 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.6254 pixels mm^-1	θmax = 29.9°, θmin = 3.4°
ω scans	h = −19→15
Absorption correction: multi-scan CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −62→59
Tmin = 0.625, Tmax = 1.000	l = −9→11
25345 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0316P)^2 + 64.828P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 3.60 e Å^−3
10741 reflections	Δρmin = −2.56 e Å^−3
639 parameters	Absolute structure: Flack x determined using 2881 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
122 restraints	Absolute structure parameter: 0.44 (5)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq
C41	0.0891 (13)	0.4906 (4)	1.432 (2)	0.016 (4)
C42	0.1229 (11)	0.5154 (3)	1.389 (2)	0.015 (4)
C43	0.0855 (12)	0.5433 (3)	1.4180 (18)	0.014 (3)
C44	0.0072 (13)	0.5424 (4)	1.500 (2)	0.017 (4)
C45	−0.0317 (11)	0.5178 (4)	1.5371 (18)	0.014 (3)
C46	0.0101 (13)	0.4915 (4)	1.517 (2)	0.012 (4)
F10	0.1974 (8)	0.5152 (2)	1.3087 (15)	0.021 (3)
F11	−0.0293 (7)	0.4656 (2)	1.5576 (13)	0.024 (3)
F12	−0.0311 (7)	0.5692 (2)	1.5238 (13)	0.024 (2)
I10	0.15074 (9)	0.45018 (3)	1.38890 (16)	0.0212 (3)
I11	0.15087 (9)	0.58138 (3)	1.35756 (15)	0.0240 (3)
I12	−0.15115 (8)	0.51842 (3)	1.65340 (14)	0.0205 (3)
C35	0.5767 (10)	0.4523 (3)	0.9055 (17)	0.009 (3)
C36	0.6151 (12)	0.4791 (4)	0.876 (2)	0.016 (4)
C37	0.5849 (11)	0.5043 (3)	0.9265 (19)	0.008 (3)
C38	0.5089 (12)	0.5045 (4)	1.014 (2)	0.010 (3)
C39	0.4664 (11)	0.4784 (3)	1.0352 (19)	0.014 (3)
C40	0.4992 (13)	0.4535 (4)	0.987 (2)	0.017 (4)
F7	0.6897 (8)	0.4797 (3)	0.7936 (15)	0.024 (3)
F8	0.4578 (7)	0.4271 (2)	1.0126 (12)	0.018 (2)
F9	0.4747 (8)	0.5305 (2)	1.0583 (14)	0.029 (3)
I7	0.62709 (9)	0.41350 (3)	0.82628 (14)	0.0208 (3)
I8	0.64812 (8)	0.54514 (3)	0.87761 (15)	0.0207 (3)
I9	0.35036 (7)	0.47876 (3)	1.16052 (13)	0.0199 (3)
C29	0.9076 (12)	0.2408 (4)	0.083 (2)	0.012 (3)
C30	0.9831 (14)	0.2429 (4)	0.008 (2)	0.014 (4)
C31	1.0263 (11)	0.2694 (3)	−0.0375 (19)	0.011 (3)
C32	0.9816 (12)	0.2956 (3)	0.014 (2)	0.012 (3)
C33	0.9029 (11)	0.2943 (3)	0.0892 (18)	0.015 (3)
C34	0.8696 (11)	0.2682 (3)	0.1254 (19)	0.013 (3)
F4	1.0194 (6)	0.2187 (2)	−0.0428 (11)	0.011 (2)
F5	1.0181 (7)	0.32054 (19)	−0.0256 (11)	0.017 (2)
F6	0.7960 (9)	0.2670 (2)	0.2065 (15)	0.022 (3)
I4	0.85103 (8)	0.20160 (3)	0.13664 (14)	0.0182 (3)
I5	1.14404 (8)	0.27090 (3)	−0.14362 (13)	0.0175 (3)
I6	0.83856 (10)	0.33305 (2)	0.14888 (13)	0.0186 (2)
C23	0.9241 (12)	0.2052 (4)	−0.397 (2)	0.020 (4)
C24	1.0019 (12)	0.2048 (4)	−0.479 (2)	0.014 (4)
C25	1.0365 (11)	0.2315 (3)	−0.5385 (18)	0.012 (3)
C26	0.9892 (14)	0.2574 (4)	−0.503 (2)	0.018 (4)*
C27	0.9121 (12)	0.2587 (4)	−0.427 (2)	0.013 (4)
C28	0.8813 (11)	0.2308 (3)	−0.3729 (18)	0.013 (3)*
F1	1.0434 (7)	0.1805 (2)	−0.5102 (13)	0.023 (2)
F2	1.0173 (7)	0.2817 (2)	−0.5593 (11)	0.014 (2)
F3	0.8098 (8)	0.2308 (2)	−0.2893 (14)	0.019 (2)
I1	0.87238 (11)	0.16578 (3)	−0.32324 (15)	0.0227 (3)
I2	1.15142 (7)	0.23121 (3)	−0.65344 (13)	0.0181 (3)
I3	0.84483 (8)	0.29669 (3)	−0.38646 (15)	0.0195 (3)
C1	0.7279 (12)	0.1275 (3)	−0.0197 (19)	0.026 (4)
C2	0.7186 (11)	0.1189 (3)	−0.177 (2)	0.024 (4)
C3	0.7932 (16)	0.1024 (4)	−0.218 (3)	0.032 (5)
H3	0.7897	0.0954	−0.3183	0.039*
C4	0.8735 (13)	0.0959 (4)	−0.114 (3)	0.032 (5)
H4	0.9245	0.0854	−0.1475	0.039*
C5	0.8802 (11)	0.1044 (4)	0.037 (2)	0.026 (4)
H5	0.9342	0.0993	0.1062	0.031*
C6	0.8027 (11)	0.1212 (4)	0.0860 (19)	0.028 (4)
C7	0.7992 (14)	0.1317 (4)	0.236 (2)	0.034 (4)
H7	0.8501	0.1283	0.3145	0.040*
C8	0.7189 (14)	0.1469 (4)	0.263 (2)	0.024 (4)
H8	0.7145	0.1534	0.3627	0.029*
C9	0.6418 (13)	0.1534 (4)	0.146 (3)	0.022 (4)
H9	0.5892	0.1649	0.1668	0.026*
C10	0.6465 (11)	0.1429 (3)	0.009 (2)	0.021 (4)
C11	0.5804 (12)	0.1461 (3)	−0.1326 (18)	0.030 (4)
H11A	0.5712	0.1670	−0.1594	0.036*
H11B	0.5179	0.1374	−0.1212	0.036*
C12	0.6263 (11)	0.1296 (3)	−0.2572 (17)	0.027 (3)
H12A	0.5859	0.1131	−0.2986	0.032*
H12B	0.6364	0.1430	−0.3407	0.032*
C5AA	0.8699 (11)	0.3777 (3)	0.7611 (17)	0.025 (3)
H5AA	0.9112	0.3610	0.7968	0.030*
H5AB	0.8589	0.3897	0.8495	0.030*
C6AA	0.9178 (11)	0.3970 (3)	0.6415 (18)	0.031 (4)
H6AA	0.9253	0.4176	0.6750	0.037*
H6AB	0.9806	0.3891	0.6264	0.037*
C13	0.7675 (9)	0.3773 (3)	0.5279 (15)	0.013 (3)
C14	0.8488 (12)	0.3945 (4)	0.501 (2)	0.026 (4)
C15	0.8487 (13)	0.4051 (4)	0.355 (2)	0.022 (4)
H15	0.9015	0.4159	0.3297	0.026*
C16	0.7699 (13)	0.3997 (4)	0.2447 (19)	0.021 (4)
H16	0.7700	0.4075	0.1461	0.025*
C17	0.6922 (11)	0.3834 (3)	0.2748 (17)	0.021 (3)
H17	0.6408	0.3800	0.1973	0.025*
C18	0.6899 (9)	0.3720 (3)	0.4198 (18)	0.022 (3)
C19	0.6169 (13)	0.3551 (4)	0.465 (3)	0.032 (5)
H19	0.5620	0.3506	0.3957	0.039*
C20	0.6263 (12)	0.3449 (3)	0.612 (2)	0.021 (4)
H20	0.5767	0.3331	0.6409	0.025*
C21	0.7047 (12)	0.3509 (4)	0.7220 (19)	0.017 (4)
H21	0.7070	0.3441	0.8228	0.021*
C22	0.7769 (10)	0.3670 (3)	0.6778 (17)	0.017 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C41	0.016 (4)	0.016 (4)	0.016 (4)	0.0003 (12)	0.0023 (13)	0.0000 (12)
C42	0.014 (4)	0.016 (4)	0.015 (4)	0.0000 (12)	0.0027 (13)	−0.0003 (12)
C43	0.024 (7)	0.009 (6)	0.009 (6)	−0.004 (5)	0.002 (5)	0.000 (5)
C44	0.019 (7)	0.015 (7)	0.016 (8)	0.004 (6)	−0.002 (6)	−0.003 (6)
C45	0.014 (6)	0.018 (7)	0.011 (7)	−0.007 (5)	0.008 (5)	−0.011 (5)
C46	0.016 (7)	0.008 (6)	0.012 (7)	0.002 (5)	0.003 (5)	0.006 (5)
F10	0.013 (5)	0.029 (6)	0.022 (6)	0.003 (4)	0.010 (4)	0.005 (4)
F11	0.025 (3)	0.021 (3)	0.026 (3)	−0.005 (2)	0.005 (2)	0.003 (2)
F12	0.025 (5)	0.022 (5)	0.027 (5)	0.002 (4)	0.012 (4)	−0.009 (4)
I10	0.0258 (6)	0.0153 (5)	0.0234 (7)	0.0082 (5)	0.0064 (5)	0.0022 (5)
I11	0.0316 (7)	0.0166 (5)	0.0252 (7)	−0.0077 (5)	0.0094 (5)	−0.0006 (4)
I12	0.0143 (6)	0.0273 (6)	0.0210 (7)	0.0011 (5)	0.0058 (5)	−0.0008 (6)
C35	0.008 (3)	0.009 (3)	0.009 (3)	−0.0004 (12)	0.0009 (13)	−0.0003 (12)
C36	0.016 (4)	0.016 (4)	0.015 (4)	0.0004 (12)	0.0024 (13)	−0.0002 (12)
C37	0.012 (6)	0.007 (6)	0.006 (6)	−0.003 (5)	0.000 (4)	0.000 (5)
C38	0.013 (7)	0.011 (7)	0.007 (6)	0.001 (5)	0.002 (5)	−0.001 (5)
C39	0.014 (4)	0.015 (4)	0.014 (4)	0.0000 (12)	0.0020 (13)	0.0001 (12)
C40	0.017 (4)	0.017 (4)	0.017 (4)	−0.0001 (12)	0.0024 (13)	0.0003 (12)
F7	0.010 (5)	0.031 (6)	0.033 (7)	0.001 (4)	0.013 (4)	−0.001 (5)
F8	0.018 (3)	0.016 (3)	0.020 (3)	−0.003 (2)	0.003 (2)	−0.002 (2)
F9	0.031 (5)	0.021 (5)	0.037 (6)	−0.004 (4)	0.016 (4)	−0.011 (4)
I7	0.0267 (6)	0.0170 (5)	0.0184 (6)	0.0048 (4)	0.0022 (5)	−0.0037 (4)
I8	0.0230 (6)	0.0174 (5)	0.0232 (6)	−0.0077 (5)	0.0080 (5)	−0.0023 (5)
I9	0.0124 (6)	0.0281 (6)	0.0198 (7)	−0.0011 (5)	0.0044 (5)	0.0001 (5)
C29	0.012 (3)	0.011 (3)	0.012 (4)	−0.0003 (12)	0.0011 (13)	0.0009 (12)
C30	0.024 (8)	0.010 (7)	0.008 (8)	0.003 (6)	−0.001 (6)	0.002 (5)
C31	0.011 (3)	0.012 (3)	0.011 (3)	0.0006 (12)	0.0016 (13)	−0.0001 (12)
C32	0.017 (7)	0.012 (7)	0.007 (7)	0.003 (6)	0.004 (5)	0.003 (5)
C33	0.015 (3)	0.015 (3)	0.015 (3)	−0.0003 (12)	0.0021 (13)	−0.0003 (12)
C34	0.013 (4)	0.013 (4)	0.013 (4)	0.0006 (12)	0.0024 (13)	−0.0004 (12)
F4	0.011 (3)	0.010 (3)	0.012 (3)	0.003 (2)	0.0033 (19)	0.000 (2)
F5	0.022 (5)	0.009 (4)	0.021 (5)	−0.006 (3)	0.002 (4)	0.001 (3)
F6	0.031 (6)	0.017 (5)	0.019 (6)	0.002 (4)	0.017 (5)	0.000 (4)
I4	0.0220 (6)	0.0154 (5)	0.0174 (6)	−0.0069 (4)	0.0031 (5)	0.0024 (4)
I5	0.0142 (6)	0.0245 (6)	0.0149 (6)	−0.0006 (5)	0.0057 (5)	0.0014 (5)
I6	0.0225 (5)	0.0164 (5)	0.0170 (5)	0.0061 (4)	0.0024 (4)	−0.0015 (4)
C23	0.020 (4)	0.020 (4)	0.020 (4)	−0.0005 (13)	0.0025 (13)	−0.0001 (13)
C24	0.014 (4)	0.014 (4)	0.014 (4)	0.0003 (12)	0.0014 (13)	0.0003 (12)
C25	0.012 (3)	0.012 (3)	0.012 (3)	0.0004 (12)	0.0018 (13)	0.0000 (12)
C27	0.008 (6)	0.012 (6)	0.018 (7)	−0.002 (5)	−0.005 (5)	0.000 (5)
F1	0.036 (5)	0.009 (4)	0.027 (5)	0.004 (4)	0.021 (4)	0.003 (4)
F2	0.016 (3)	0.011 (3)	0.016 (3)	−0.002 (2)	0.003 (2)	0.001 (2)
F3	0.019 (5)	0.021 (5)	0.020 (6)	0.001 (4)	0.013 (4)	0.000 (4)
I1	0.0310 (6)	0.0162 (5)	0.0218 (6)	−0.0073 (4)	0.0066 (5)	0.0009 (4)
I2	0.0096 (5)	0.0290 (6)	0.0167 (7)	0.0002 (5)	0.0056 (5)	0.0005 (5)
I3	0.0227 (6)	0.0169 (5)	0.0198 (7)	0.0054 (5)	0.0060 (5)	−0.0014 (4)
C1	0.039 (9)	0.011 (6)	0.028 (9)	−0.011 (6)	0.006 (7)	0.001 (6)
C2	0.019 (7)	0.013 (7)	0.041 (10)	−0.003 (6)	0.007 (6)	0.010 (6)
C3	0.043 (11)	0.013 (8)	0.042 (12)	−0.008 (8)	0.013 (9)	0.004 (8)
C4	0.024 (9)	0.018 (9)	0.060 (14)	0.000 (7)	0.025 (9)	−0.009 (8)
C5	0.015 (8)	0.026 (9)	0.033 (10)	−0.004 (7)	−0.009 (7)	0.015 (7)
C6	0.028 (4)	0.028 (4)	0.029 (4)	−0.0008 (13)	0.0040 (13)	0.0001 (13)
C7	0.040 (11)	0.026 (9)	0.035 (11)	−0.019 (8)	0.004 (8)	0.005 (8)
C8	0.028 (9)	0.022 (9)	0.025 (9)	−0.014 (7)	0.010 (7)	−0.006 (7)
C9	0.015 (7)	0.016 (8)	0.035 (10)	−0.004 (6)	0.003 (7)	−0.007 (7)
C10	0.018 (8)	0.006 (6)	0.036 (10)	−0.002 (6)	−0.012 (7)	0.007 (6)
C11	0.033 (9)	0.024 (8)	0.036 (9)	0.004 (7)	0.014 (7)	−0.007 (7)
C12	0.032 (8)	0.020 (8)	0.027 (8)	0.007 (7)	0.000 (7)	0.006 (6)
C5AA	0.030 (8)	0.012 (7)	0.030 (8)	0.000 (6)	−0.003 (7)	0.000 (6)
C6AA	0.025 (8)	0.025 (8)	0.038 (10)	−0.002 (7)	−0.016 (7)	0.003 (7)
C13	0.013 (3)	0.012 (3)	0.013 (3)	0.0003 (12)	0.0013 (13)	−0.0004 (12)
C14	0.040 (10)	0.016 (7)	0.025 (9)	0.012 (7)	0.018 (7)	0.010 (6)
C15	0.026 (9)	0.020 (8)	0.022 (9)	0.009 (7)	0.007 (7)	0.007 (7)
C16	0.036 (10)	0.018 (7)	0.007 (8)	0.007 (7)	−0.005 (7)	0.002 (6)
C17	0.031 (8)	0.017 (7)	0.012 (7)	0.011 (7)	−0.011 (6)	−0.006 (6)
C18	0.009 (6)	0.008 (6)	0.047 (9)	0.004 (5)	−0.001 (6)	−0.009 (6)
C19	0.026 (9)	0.010 (7)	0.061 (14)	0.004 (7)	0.008 (9)	−0.006 (8)
C20	0.014 (7)	0.015 (7)	0.032 (11)	−0.004 (6)	−0.001 (7)	−0.014 (7)
C21	0.015 (7)	0.020 (8)	0.018 (9)	0.007 (6)	0.005 (6)	0.001 (6)
C22	0.017 (3)	0.017 (3)	0.017 (3)	0.0000 (13)	0.0021 (13)	−0.0006 (13)

Geometric parameters (Å, º)

C41—C42	1.31 (2)	C1—C2	1.45 (2)
C41—C46	1.44 (3)	C1—C6	1.35 (2)
C41—I10	2.102 (18)	C1—C10	1.41 (2)
C42—C43	1.42 (2)	C2—C3	1.39 (3)
C42—F10	1.36 (2)	C2—C12	1.49 (2)
C43—C44	1.41 (3)	C3—H3	0.9500
C43—I11	2.076 (16)	C3—C4	1.40 (3)
C44—C45	1.31 (2)	C4—H4	0.9500
C44—F12	1.37 (2)	C4—C5	1.39 (3)
C45—C46	1.36 (2)	C5—H5	0.9500
C45—I12	2.106 (16)	C5—C6	1.46 (2)
C46—F11	1.38 (2)	C6—C7	1.43 (2)
C35—C36	1.38 (2)	C7—H7	0.9500
C35—C40	1.40 (3)	C7—C8	1.39 (3)
C35—I7	2.073 (14)	C8—H8	0.9500
C36—C37	1.33 (2)	C8—C9	1.44 (3)
C36—F7	1.37 (2)	C9—H9	0.9500
C37—C38	1.42 (3)	C9—C10	1.32 (3)
C37—I8	2.139 (15)	C10—C11	1.48 (2)
C38—C39	1.36 (2)	C11—H11A	0.9900
C38—F9	1.36 (2)	C11—H11B	0.9900
C39—C40	1.32 (2)	C11—C12	1.56 (2)
C39—I9	2.114 (17)	C12—H12A	0.9900
C40—F8	1.37 (2)	C12—H12B	0.9900
C29—C30	1.34 (3)	C5AA—H5AA	0.9900
C29—C34	1.44 (2)	C5AA—H5AB	0.9900
C29—I4	2.045 (17)	C5AA—C6AA	1.61 (2)
C30—C31	1.44 (2)	C5AA—C22	1.509 (19)
C30—F4	1.32 (2)	C6AA—H6AA	0.9900
C31—C32	1.46 (2)	C6AA—H6AB	0.9900
C31—I5	2.033 (17)	C6AA—C14	1.49 (2)
C32—C33	1.38 (2)	C13—C14	1.45 (2)
C32—F5	1.317 (19)	C13—C18	1.386 (19)
C33—C34	1.34 (2)	C13—C22	1.41 (2)
C33—I6	2.094 (16)	C14—C15	1.39 (3)
C34—F6	1.35 (2)	C15—H15	0.9500
C23—C24	1.40 (3)	C15—C16	1.41 (2)
C23—C28	1.35 (2)	C16—H16	0.9500
C23—I1	2.086 (18)	C16—C17	1.39 (3)
C24—C25	1.45 (2)	C17—H17	0.9500
C24—F1	1.30 (2)	C17—C18	1.40 (2)
C25—C26	1.41 (3)	C18—C19	1.40 (2)
C25—I2	2.042 (17)	C19—H19	0.9500
C26—C27	1.37 (3)	C19—C20	1.38 (3)
C26—F2	1.30 (2)	C20—H20	0.9500
C27—C28	1.45 (2)	C20—C21	1.41 (2)
C27—I3	2.039 (18)	C21—H21	0.9500
C28—F3	1.34 (2)	C21—C22	1.36 (2)
C42—C41—C46	118.4 (17)	C2—C3—H3	119.2
C42—C41—I10	121.8 (14)	C2—C3—C4	122 (2)
C46—C41—I10	119.8 (13)	C4—C3—H3	119.2
C41—C42—C43	124.2 (16)	C3—C4—H4	119.2
C41—C42—F10	119.6 (15)	C5—C4—C3	121.5 (19)
F10—C42—C43	116.2 (15)	C5—C4—H4	119.2
C42—C43—I11	120.9 (12)	C4—C5—H5	120.6
C44—C43—C42	114.1 (15)	C4—C5—C6	118.8 (15)
C44—C43—I11	124.9 (12)	C6—C5—H5	120.6
C45—C44—C43	123.0 (17)	C1—C6—C5	117.1 (15)
C45—C44—F12	122.5 (17)	C1—C6—C7	117.3 (16)
F12—C44—C43	114.2 (15)	C7—C6—C5	125.5 (16)
C44—C45—C46	120.9 (17)	C6—C7—H7	121.2
C44—C45—I12	120.5 (13)	C8—C7—C6	117.5 (17)
C46—C45—I12	118.2 (13)	C8—C7—H7	121.2
C45—C46—C41	118.7 (17)	C7—C8—H8	118.5
C45—C46—F11	121.5 (17)	C7—C8—C9	123.0 (19)
F11—C46—C41	119.2 (16)	C9—C8—H8	118.5
C36—C35—C40	115.1 (15)	C8—C9—H9	121.1
C36—C35—I7	122.1 (12)	C10—C9—C8	117.9 (18)
C40—C35—I7	122.8 (12)	C10—C9—H9	121.1
C37—C36—C35	123.4 (16)	C1—C10—C11	109.6 (15)
C37—C36—F7	118.4 (16)	C9—C10—C1	119.6 (14)
F7—C36—C35	118.2 (15)	C9—C10—C11	130.7 (16)
C36—C37—C38	119.8 (16)	C10—C11—H11A	110.4
C36—C37—I8	121.4 (13)	C10—C11—H11B	110.4
C38—C37—I8	118.8 (12)	C10—C11—C12	106.7 (13)
C39—C38—C37	117.3 (16)	H11A—C11—H11B	108.6
C39—C38—F9	122.8 (16)	C12—C11—H11A	110.4
F9—C38—C37	119.4 (15)	C12—C11—H11B	110.4
C38—C39—I9	117.4 (13)	C2—C12—C11	103.9 (13)
C40—C39—C38	121.7 (17)	C2—C12—H12A	111.0
C40—C39—I9	120.8 (13)	C2—C12—H12B	111.0
C39—C40—C35	122.5 (17)	C11—C12—H12A	111.0
C39—C40—F8	121.7 (17)	C11—C12—H12B	111.0
F8—C40—C35	115.8 (15)	H12A—C12—H12B	109.0
C30—C29—C34	115.0 (16)	H5AA—C5AA—H5AB	108.7
C30—C29—I4	123.2 (14)	C6AA—C5AA—H5AA	110.6
C34—C29—I4	121.8 (13)	C6AA—C5AA—H5AB	110.6
C29—C30—C31	127.0 (18)	C22—C5AA—H5AA	110.6
F4—C30—C29	118.9 (17)	C22—C5AA—H5AB	110.6
F4—C30—C31	113.8 (17)	C22—C5AA—C6AA	105.7 (11)
C30—C31—C32	112.5 (16)	C5AA—C6AA—H6AA	111.1
C30—C31—I5	124.7 (13)	C5AA—C6AA—H6AB	111.1
C32—C31—I5	122.6 (12)	H6AA—C6AA—H6AB	109.1
C33—C32—C31	122.1 (15)	C14—C6AA—C5AA	103.3 (12)
F5—C32—C31	115.0 (15)	C14—C6AA—H6AA	111.1
F5—C32—C33	122.8 (15)	C14—C6AA—H6AB	111.1
C32—C33—I6	119.8 (12)	C18—C13—C14	123.9 (13)
C34—C33—C32	119.5 (15)	C18—C13—C22	124.7 (13)
C34—C33—I6	120.7 (12)	C22—C13—C14	111.4 (12)
C33—C34—C29	123.7 (16)	C13—C14—C6AA	110.5 (13)
C33—C34—F6	119.3 (15)	C15—C14—C6AA	133.0 (17)
F6—C34—C29	116.9 (14)	C15—C14—C13	116.5 (16)
C24—C23—I1	119.1 (13)	C14—C15—H15	120.2
C28—C23—C24	120.1 (16)	C14—C15—C16	119.7 (18)
C28—C23—I1	120.8 (13)	C16—C15—H15	120.2
C23—C24—C25	120.7 (16)	C15—C16—H16	118.8
F1—C24—C23	122.4 (16)	C17—C16—C15	122.4 (16)
F1—C24—C25	116.9 (16)	C17—C16—H16	118.8
C24—C25—I2	121.0 (12)	C16—C17—H17	120.1
C26—C25—C24	115.3 (16)	C16—C17—C18	119.7 (13)
C26—C25—I2	123.6 (13)	C18—C17—H17	120.1
C27—C26—C25	125.8 (19)	C13—C18—C17	117.7 (13)
F2—C26—C25	116.6 (18)	C13—C18—C19	116.7 (15)
F2—C26—C27	117.4 (18)	C19—C18—C17	125.6 (15)
C26—C27—C28	115.2 (17)	C18—C19—H19	120.7
C26—C27—I3	123.7 (14)	C20—C19—C18	118.6 (17)
C28—C27—I3	121.1 (13)	C20—C19—H19	120.7
C23—C28—C27	122.9 (16)	C19—C20—H20	117.9
F3—C28—C23	119.0 (16)	C19—C20—C21	124.2 (18)
F3—C28—C27	118.0 (15)	C21—C20—H20	117.9
C6—C1—C2	125.4 (15)	C20—C21—H21	121.3
C6—C1—C10	124.5 (16)	C22—C21—C20	117.4 (16)
C10—C1—C2	110.1 (14)	C22—C21—H21	121.3
C1—C2—C12	109.7 (14)	C13—C22—C5AA	109.0 (13)
C3—C2—C1	115.4 (16)	C21—C22—C5AA	132.5 (14)
C3—C2—C12	134.9 (17)	C21—C22—C13	118.4 (13)