Phase behaviour and crystal structures of 2′,3′-di­fluorinated p-terphenyl derivatives

The crystal structures of difluorine derivatives of p-terphenyls (nTm) have been determined by single-crystal X-ray diffraction. For the unsymmetrical substituted com­pounds 2′,3′-di­fluoro-4-methyl-p-terphenyl (1T0, C₁₉H₁₄F₂) and 4-ethyl-2′,3′-di­fluoro-4′′-methyl-p-terphenyl (1T2, C₂₁H₁₈F₂), the crystal structure is disordered, with mol­ecules statistically entering the crystal in up and down orientations, with full superposition of all the atoms, except for those of the terminal groups (H/methyl for 1T0 and meth­yl/ethyl for 1T2). For triclinic 2′,3′-di­fluoro-4,4′′-dimethyl-p-terphenyl (1T1, C₂₀H₁₆F₂), with the space group P, the two crystallographically independent mol­ecules have the same conformation, which is different from monoclinic 1T0 (space group C2) and 1T2 (space group C2/c). A common feature of the conformation of the three com­pounds is the noncoplanar twisted arrangement of the three rings of the p-ter­phenyl moiety. Two-dimensional (2D) Hirshfeld fingerprint plots are con­sistent with H...H and C...H contacts in the crystal packing. For the three com­pounds, the phase behaviour has been investigated by POM (Petra/Osiris/Molinspiration) and differential scanning calorimetry (DSC) analysis. 1T2 is mesogenic, with enanti­otropic nematic behaviour.

Computing details

For all structures, data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020) and VESTA (Momma & Izumi, 2011); software used to prepare material for publication: WinGX (Farrugia, 2012) and PARST97 (Nardelli, 1983, 1995).

2',3'-Difluoro-4-methyl-p-terphenyl (1T0)

Crystal data

C19H14F2	F(000) = 584
Mr = 280.30	Dx = 1.369 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 17.246 (5) Å	Cell parameters from 221 reflections
b = 6.039 (3) Å	θ = 2.6–28.9°
c = 13.062 (4) Å	µ = 0.10 mm^−1
β = 90.88 (2)°	T = 173 K
V = 1360.2 (9) Å^3	Prism, colourless
Z = 4	0.40 × 0.25 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	2603 independent reflections
Radiation source: normal-focus sealed tube	2209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
CCD rotation images, thick slices scans	h = −22→21
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −6→7
Tmin = 0.935, Tmax = 0.953	l = −15→16
4359 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 2.7631P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2603 reflections	Δρmax = 0.46 e Å^−3
202 parameters	Δρmin = −0.22 e Å^−3
1 restraint	Absolute structure: Flack x determined using 717 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.0 (7)

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. The crystal structure is disordered, with molecules statistically entering the crystal in up and down orientations, with full superposition of all the atoms but those of the terminal groups (H/Methyl).

All data for crystal structure determinations were measured on a Bruker-Nonius Kappa CCD diffractometer equipped with an Oxford Cryostream 700 apparatus, using graphite monochromated Mo Kα radiation (0.71073 Å). Reduction of data and semi-empirical absorption correction were done using SADABS program (Bruker–Nonius, 2002). The structures were solved by direct methods SIR97 program (Altomare et al., 1999) and refined by the full-matrix least-squares method on F² using the SHELXL2015 program (Sheldrick, 2015) with the aid of the program WinGX (Farrugia, 2012). The analysis of the crystal packing was performed using the program Mercury (Macrae et al., 2020) and some calculations were performed using PARST97 (Nardelli, 1983, 1995).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4232 (3)	0.2311 (9)	0.6632 (4)	0.0369 (11)
H1	0.395710	0.362508	0.645893	0.044*
C2	0.4660 (3)	0.2213 (9)	0.7526 (4)	0.0394 (11)
H2	0.466852	0.345413	0.797280	0.047*
C3	0.5080 (3)	0.0327 (10)	0.7787 (4)	0.0412 (12)
H3B	0.537807	0.027362	0.840485	0.049*	0.489 (14)
C19A	0.5518 (6)	0.022 (2)	0.8752 (9)	0.053 (4)	0.511 (14)
H19A	0.526351	−0.080676	0.921911	0.079*	0.511 (14)
H19B	0.553856	0.169985	0.906282	0.079*	0.511 (14)
H19C	0.604638	−0.029166	0.862160	0.079*	0.511 (14)
C4	0.5057 (3)	−0.1478 (9)	0.7129 (4)	0.0393 (12)
H4	0.534817	−0.276867	0.729298	0.047*
C5	0.4618 (2)	−0.1420 (8)	0.6248 (3)	0.0345 (11)
H5	0.459752	−0.268737	0.581734	0.041*
C6	0.4199 (2)	0.0479 (8)	0.5972 (3)	0.0324 (10)
C7	0.3730 (2)	0.0514 (8)	0.5017 (3)	0.0317 (10)
C8	0.3731 (2)	0.2265 (8)	0.4330 (4)	0.0323 (10)
C9	0.3309 (3)	0.2263 (8)	0.3431 (3)	0.0319 (10)
C10	0.2840 (2)	0.0487 (8)	0.3141 (3)	0.0330 (11)
C11	0.2839 (2)	−0.1297 (9)	0.3829 (3)	0.0340 (11)
H11	0.253475	−0.256380	0.366483	0.041*
C12	0.3259 (2)	−0.1285 (9)	0.4727 (3)	0.0342 (10)
H12	0.323050	−0.253189	0.516829	0.041*
C13	0.2384 (2)	0.0465 (9)	0.2176 (4)	0.0345 (11)
C14	0.1911 (3)	0.2246 (9)	0.1883 (4)	0.0388 (11)
H14	0.190023	0.354205	0.229485	0.047*
C15	0.1462 (3)	0.2139 (10)	0.1004 (4)	0.0441 (12)
H15	0.114451	0.336454	0.081643	0.053*
C16	0.1465 (3)	0.0267 (11)	0.0386 (4)	0.0458 (13)
H16A	0.115194	0.019601	−0.021775	0.055*	0.511 (14)
C19B	0.0906 (8)	0.014 (3)	−0.0466 (9)	0.063 (4)	0.489 (14)
H19D	0.038800	−0.016314	−0.020016	0.094*	0.489 (14)
H19E	0.105562	−0.105640	−0.093075	0.094*	0.489 (14)
H19F	0.089926	0.154745	−0.083792	0.094*	0.489 (14)
C17	0.1939 (3)	−0.1512 (10)	0.0675 (4)	0.0445 (13)
H17	0.194961	−0.280488	0.026089	0.053*
C18	0.2387 (3)	−0.1410 (8)	0.1546 (4)	0.0382 (11)
H18	0.270721	−0.263356	0.172709	0.046*
F1	0.33812 (15)	0.4027 (6)	0.28040 (19)	0.0422 (7)
F2	0.41870 (14)	0.4067 (6)	0.45245 (19)	0.0402 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.030 (2)	0.037 (3)	0.043 (2)	0.000 (2)	0.0095 (18)	−0.003 (2)
C2	0.041 (2)	0.040 (3)	0.038 (2)	−0.006 (2)	0.0102 (19)	−0.007 (2)
C3	0.038 (2)	0.050 (3)	0.036 (2)	−0.008 (2)	0.0034 (19)	0.005 (2)
C19A	0.040 (6)	0.063 (8)	0.056 (7)	0.004 (5)	−0.002 (5)	0.000 (6)
C4	0.037 (2)	0.037 (3)	0.044 (3)	0.001 (2)	0.0116 (19)	0.003 (2)
C5	0.034 (2)	0.032 (3)	0.038 (2)	−0.0009 (19)	0.0118 (17)	0.0020 (19)
C6	0.025 (2)	0.031 (3)	0.041 (2)	−0.0020 (18)	0.0140 (17)	−0.001 (2)
C7	0.025 (2)	0.032 (3)	0.039 (2)	0.0038 (19)	0.0125 (17)	0.000 (2)
C8	0.031 (2)	0.023 (3)	0.043 (3)	−0.0009 (19)	0.0099 (18)	−0.0040 (19)
C9	0.032 (2)	0.026 (3)	0.037 (2)	0.0023 (19)	0.0096 (17)	0.0036 (19)
C10	0.030 (2)	0.032 (3)	0.038 (2)	0.001 (2)	0.0105 (17)	−0.002 (2)
C11	0.0277 (19)	0.032 (3)	0.042 (2)	−0.001 (2)	0.0091 (16)	0.001 (2)
C12	0.030 (2)	0.026 (3)	0.046 (2)	0.000 (2)	0.0134 (17)	0.002 (2)
C13	0.028 (2)	0.037 (3)	0.040 (2)	−0.002 (2)	0.0097 (18)	0.003 (2)
C14	0.037 (2)	0.034 (3)	0.046 (3)	0.002 (2)	0.0130 (19)	0.000 (2)
C15	0.037 (2)	0.045 (3)	0.050 (3)	0.004 (2)	0.002 (2)	0.008 (3)
C16	0.038 (3)	0.054 (4)	0.045 (3)	−0.005 (2)	−0.001 (2)	0.005 (3)
C19B	0.075 (9)	0.072 (10)	0.041 (6)	−0.007 (7)	0.002 (6)	−0.009 (6)
C17	0.042 (3)	0.045 (4)	0.046 (3)	−0.001 (2)	0.003 (2)	−0.005 (2)
C18	0.033 (2)	0.030 (3)	0.052 (3)	0.002 (2)	0.0075 (19)	−0.002 (2)
F1	0.0469 (14)	0.0309 (15)	0.0488 (15)	−0.0031 (14)	0.0021 (11)	0.0061 (14)
F2	0.0417 (13)	0.0309 (14)	0.0481 (14)	−0.0072 (13)	0.0026 (11)	−0.0017 (14)

Geometric parameters (Å, º)

C1—C2	1.373 (7)	C9—C10	1.392 (7)
C1—C6	1.403 (7)	C10—C11	1.403 (7)
C1—H1	0.9500	C10—C13	1.476 (7)
C2—C3	1.390 (8)	C11—C12	1.369 (6)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.388 (8)	C12—H12	0.9500
C3—C19A	1.460 (11)	C13—C18	1.399 (7)
C3—H3B	0.9500	C13—C14	1.399 (7)
C19A—H19A	0.9800	C14—C15	1.377 (7)
C19A—H19B	0.9800	C14—H14	0.9500
C19A—H19C	0.9800	C15—C16	1.389 (9)
C4—C5	1.368 (7)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.398 (8)
C5—C6	1.400 (7)	C16—C19B	1.464 (12)
C5—H5	0.9500	C16—H16A	0.9500
C6—C7	1.477 (6)	C19B—H19D	0.9800
C7—C8	1.387 (7)	C19B—H19E	0.9800
C7—C12	1.405 (7)	C19B—H19F	0.9800
C8—F2	1.365 (5)	C17—C18	1.368 (7)
C8—C9	1.372 (6)	C17—H17	0.9500
C9—F1	1.350 (5)	C18—H18	0.9500
C2—C1—C6	120.3 (5)	C9—C10—C11	115.1 (4)
C2—C1—H1	119.8	C9—C10—C13	122.6 (4)
C6—C1—H1	119.8	C11—C10—C13	122.3 (5)
C1—C2—C3	121.0 (5)	C12—C11—C10	122.6 (5)
C1—C2—H2	119.5	C12—C11—H11	118.7
C3—C2—H2	119.5	C10—C11—H11	118.7
C4—C3—C2	118.7 (4)	C11—C12—C7	122.1 (5)
C4—C3—C19A	120.7 (7)	C11—C12—H12	119.0
C2—C3—C19A	120.5 (7)	C7—C12—H12	119.0
C4—C3—H3B	120.6	C18—C13—C14	118.0 (4)
C2—C3—H3B	120.6	C18—C13—C10	120.2 (5)
C3—C19A—H19A	109.5	C14—C13—C10	121.8 (5)
C3—C19A—H19B	109.5	C15—C14—C13	120.6 (5)
H19A—C19A—H19B	109.5	C15—C14—H14	119.7
C3—C19A—H19C	109.5	C13—C14—H14	119.7
H19A—C19A—H19C	109.5	C14—C15—C16	121.0 (5)
H19B—C19A—H19C	109.5	C14—C15—H15	119.5
C5—C4—C3	120.8 (5)	C16—C15—H15	119.5
C5—C4—H4	119.6	C15—C16—C17	118.5 (5)
C3—C4—H4	119.6	C15—C16—C19B	118.5 (8)
C4—C5—C6	120.9 (5)	C17—C16—C19B	122.7 (8)
C4—C5—H5	119.5	C15—C16—H16A	120.8
C6—C5—H5	119.5	C17—C16—H16A	120.8
C5—C6—C1	118.2 (4)	C16—C19B—H19D	109.5
C5—C6—C7	120.2 (4)	C16—C19B—H19E	109.5
C1—C6—C7	121.6 (5)	H19D—C19B—H19E	109.5
C8—C7—C12	115.0 (4)	C16—C19B—H19F	109.5
C8—C7—C6	123.5 (5)	H19D—C19B—H19F	109.5
C12—C7—C6	121.6 (4)	H19E—C19B—H19F	109.5
F2—C8—C9	117.2 (4)	C18—C17—C16	120.7 (5)
F2—C8—C7	119.6 (4)	C18—C17—H17	119.7
C9—C8—C7	123.2 (4)	C16—C17—H17	119.7
F1—C9—C8	117.7 (4)	C17—C18—C13	121.2 (5)
F1—C9—C10	120.1 (4)	C17—C18—H18	119.4
C8—C9—C10	122.1 (4)	C13—C18—H18	119.4
C6—C1—C2—C3	1.3 (7)	C8—C9—C10—C11	−0.6 (6)
C1—C2—C3—C4	−0.5 (7)	F1—C9—C10—C13	−2.4 (6)
C1—C2—C3—C19A	−178.6 (7)	C8—C9—C10—C13	−180.0 (4)
C2—C3—C4—C5	−1.1 (7)	C9—C10—C11—C12	0.9 (6)
C19A—C3—C4—C5	177.0 (7)	C13—C10—C11—C12	−179.8 (4)
C3—C4—C5—C6	1.8 (7)	C10—C11—C12—C7	−0.8 (7)
C4—C5—C6—C1	−1.0 (6)	C8—C7—C12—C11	0.4 (6)
C4—C5—C6—C7	179.9 (4)	C6—C7—C12—C11	−178.0 (4)
C2—C1—C6—C5	−0.6 (6)	C9—C10—C13—C18	133.9 (5)
C2—C1—C6—C7	178.5 (4)	C11—C10—C13—C18	−45.5 (6)
C5—C6—C7—C8	−134.8 (5)	C9—C10—C13—C14	−49.0 (6)
C1—C6—C7—C8	46.1 (6)	C11—C10—C13—C14	131.6 (5)
C5—C6—C7—C12	43.5 (5)	C18—C13—C14—C15	0.4 (7)
C1—C6—C7—C12	−135.6 (5)	C10—C13—C14—C15	−176.8 (4)
C12—C7—C8—F2	−178.1 (3)	C13—C14—C15—C16	0.0 (8)
C6—C7—C8—F2	0.3 (6)	C14—C15—C16—C17	−0.3 (8)
C12—C7—C8—C9	−0.2 (6)	C14—C15—C16—C19B	172.5 (8)
C6—C7—C8—C9	178.2 (4)	C15—C16—C17—C18	0.2 (8)
F2—C8—C9—F1	0.6 (6)	C19B—C16—C17—C18	−172.4 (7)
C7—C8—C9—F1	−177.4 (4)	C16—C17—C18—C13	0.3 (7)
F2—C8—C9—C10	178.3 (4)	C14—C13—C18—C17	−0.5 (7)
C7—C8—C9—C10	0.3 (7)	C10—C13—C18—C17	176.7 (4)
F1—C9—C10—C11	177.0 (4)

4-Ethyl-2',3'-difluoro-4''-methyl-p-terphenyl (1T2)

Crystal data

C21H18F2	F(000) = 1296
Mr = 308.35	Dx = 1.315 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.817 (4) Å	Cell parameters from 280 reflections
b = 6.014 (3) Å	θ = 26.2–3.0°
c = 29.175 (6) Å	µ = 0.09 mm^−1
β = 94.97 (2)°	T = 173 K
V = 3114.4 (18) Å^3	Prism, colourless
Z = 8	0.50 × 0.20 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	2683 independent reflections
Radiation source: normal-focus sealed tube	1565 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 9 pixels mm^-1	θmax = 25.0°, θmin = 3.5°
CCD rotation images, thick slices scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −3→7
Tmin = 0.963, Tmax = 0.975	l = −34→26
5745 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.224	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0793P)^2 + 7.9775P] where P = (Fo^2 + 2Fc^2)/3
2683 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.25 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.

Refinement. The crystal structure is disordered, with molecules statistically entering the crystal in up and down orientations, with full superposition of all the atoms but those of the terminal groups (Me/Et).

All data for crystal structure determinations were measured on a Bruker-Nonius Kappa CCD diffractometer equipped with an Oxford Cryostream 700 apparatus, using graphite monochromated Mo Kα radiation (0.71073 Å). Reduction of data and semi-empirical absorption correction were done using SADABS program (Bruker–Nonius, 2002). The structures were solved by direct methods SIR97 program (Altomare et al., 1999) and refined by the full-matrix least-squares method on F² using the SHELXL2015 program (Sheldrick, 2015) with the aid of the program WinGX (Farrugia, 2012). The analysis of the crystal packing was performed using the program Mercury (Macrae et al., 2020) and some calculations were performed using PARST97 (Nardelli, 1983, 1995).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2	0.9892 (2)	0.0936 (7)	0.62848 (15)	0.0419 (11)
C3	0.9878 (2)	−0.0850 (7)	0.65862 (15)	0.0402 (11)
H3	1.012883	−0.215523	0.652229	0.048*
C4	0.9499 (2)	−0.0726 (7)	0.69783 (14)	0.0359 (10)
H4	0.950122	−0.194520	0.717441	0.043*
C5	0.9112 (2)	0.1206 (6)	0.70862 (14)	0.0312 (9)
C6	0.9124 (2)	0.2989 (7)	0.67832 (14)	0.0364 (10)
H6	0.887227	0.429452	0.684640	0.044*
C7	0.9502 (2)	0.2857 (7)	0.63896 (15)	0.0411 (11)
H7	0.949666	0.406865	0.619138	0.049*
C8	0.8713 (2)	0.1283 (6)	0.75079 (14)	0.0319 (10)
C9	0.8250 (2)	−0.0483 (7)	0.76286 (14)	0.0356 (10)
H9	0.818639	−0.170855	0.743485	0.043*
C10	0.7888 (2)	−0.0436 (6)	0.80265 (14)	0.0338 (10)
H10	0.759644	−0.165137	0.809696	0.041*
C11	0.7943 (2)	0.1362 (6)	0.83271 (14)	0.0334 (10)
C12	0.8405 (2)	0.3097 (6)	0.82049 (14)	0.0333 (10)
C13	0.8764 (2)	0.3067 (6)	0.78115 (14)	0.0334 (10)
C14	0.7550 (2)	0.1385 (6)	0.87513 (14)	0.0322 (10)
C15	0.7565 (2)	−0.0477 (7)	0.90371 (14)	0.0394 (11)
H15	0.783727	−0.172387	0.896188	0.047*
C16	0.7182 (2)	−0.0510 (7)	0.94310 (15)	0.0431 (11)
H16	0.720113	−0.177846	0.961394	0.052*
C17	0.6768 (3)	0.1321 (8)	0.95576 (15)	0.0458 (12)
C18	0.6763 (2)	0.3174 (8)	0.92740 (15)	0.0439 (12)
H18	0.649690	0.442762	0.935307	0.053*
C19	0.7135 (2)	0.3231 (7)	0.88810 (15)	0.0402 (11)
H19	0.711143	0.450288	0.869914	0.048*
F1	0.92218 (13)	0.4820 (3)	0.77330 (8)	0.0421 (7)
F2	0.85307 (13)	0.4863 (4)	0.84920 (8)	0.0441 (7)
C1A	1.031 (3)	0.079 (6)	0.5846 (16)	0.055 (3)	0.673 (10)
H1A1	0.995851	0.058056	0.558300	0.082*	0.673 (10)
H1A2	1.065865	−0.044042	0.587101	0.082*	0.673 (10)
H1A3	1.059002	0.214327	0.580965	0.082*	0.673 (10)
C20A	0.638 (3)	0.138 (7)	1.0004 (15)	0.065 (4)	0.673 (10)
H20A	0.674336	0.187048	1.025030	0.078*	0.673 (10)
H20B	0.598007	0.247439	0.997216	0.078*	0.673 (10)
C21A	0.6074 (7)	−0.0664 (16)	1.0132 (4)	0.098 (4)	0.673 (10)
H21A	0.572072	−0.118627	0.988856	0.147*	0.673 (10)
H21B	0.582044	−0.046358	1.040653	0.147*	0.673 (10)
H21C	0.647054	−0.173477	1.018869	0.147*	0.673 (10)
C1B	0.632 (5)	0.123 (16)	0.995 (3)	0.065 (4)	0.327 (10)
H20C	0.632157	0.266309	1.010008	0.097*	0.327 (10)
H20D	0.652606	0.014324	1.016956	0.097*	0.327 (10)
H20E	0.580817	0.083117	0.985254	0.097*	0.327 (10)
C20B	1.029 (6)	0.086 (13)	0.587 (3)	0.055 (3)	0.327 (10)
H1B1	1.003158	0.182340	0.564613	0.066*	0.327 (10)
H1B2	1.078972	0.148732	0.594907	0.066*	0.327 (10)
C21B	1.0382 (14)	−0.128 (4)	0.5667 (7)	0.102 (9)	0.327 (10)
H21D	1.075130	−0.212657	0.585218	0.153*	0.327 (10)
H21E	1.054560	−0.108960	0.536446	0.153*	0.327 (10)
H21F	0.990946	−0.205653	0.564578	0.153*	0.327 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.033 (2)	0.054 (3)	0.037 (3)	−0.009 (2)	−0.003 (2)	−0.004 (2)
C3	0.041 (3)	0.037 (2)	0.041 (3)	−0.001 (2)	−0.004 (2)	−0.004 (2)
C4	0.037 (2)	0.033 (2)	0.037 (2)	0.0009 (18)	−0.003 (2)	−0.0029 (19)
C5	0.026 (2)	0.031 (2)	0.034 (2)	−0.0063 (17)	−0.0090 (18)	0.0025 (18)
C6	0.034 (2)	0.034 (2)	0.040 (3)	−0.0011 (18)	−0.002 (2)	0.005 (2)
C7	0.040 (3)	0.042 (3)	0.040 (3)	−0.006 (2)	−0.003 (2)	0.008 (2)
C8	0.030 (2)	0.030 (2)	0.033 (2)	0.0032 (17)	−0.0065 (19)	0.0045 (18)
C9	0.035 (2)	0.030 (2)	0.041 (3)	−0.0011 (17)	−0.005 (2)	−0.0026 (19)
C10	0.027 (2)	0.032 (2)	0.042 (2)	−0.0026 (17)	0.0002 (19)	0.0007 (19)
C11	0.031 (2)	0.029 (2)	0.037 (2)	0.0013 (18)	−0.0090 (19)	0.0045 (18)
C12	0.034 (2)	0.026 (2)	0.039 (3)	0.0009 (18)	−0.004 (2)	−0.0035 (18)
C13	0.034 (2)	0.028 (2)	0.037 (2)	−0.0038 (18)	−0.004 (2)	0.0047 (19)
C14	0.024 (2)	0.037 (2)	0.034 (2)	−0.0032 (18)	−0.0037 (18)	−0.0002 (19)
C15	0.038 (2)	0.039 (2)	0.041 (3)	0.0020 (19)	−0.001 (2)	0.000 (2)
C16	0.046 (3)	0.046 (3)	0.036 (3)	−0.007 (2)	−0.001 (2)	0.003 (2)
C17	0.040 (3)	0.058 (3)	0.040 (3)	−0.009 (2)	0.005 (2)	−0.009 (2)
C18	0.037 (3)	0.046 (3)	0.049 (3)	0.004 (2)	0.007 (2)	−0.009 (2)
C19	0.036 (2)	0.038 (2)	0.044 (3)	0.004 (2)	−0.006 (2)	−0.002 (2)
F1	0.0430 (14)	0.0319 (13)	0.0512 (15)	−0.0094 (11)	0.0022 (11)	0.0011 (11)
F2	0.0508 (16)	0.0341 (13)	0.0469 (15)	−0.0061 (12)	0.0014 (12)	−0.0081 (12)
C1A	0.046 (5)	0.075 (5)	0.044 (6)	−0.003 (3)	0.006 (4)	−0.004 (4)
C20A	0.059 (8)	0.081 (8)	0.056 (9)	−0.020 (6)	0.017 (6)	−0.021 (7)
C21A	0.125 (10)	0.081 (7)	0.097 (8)	−0.001 (6)	0.063 (8)	0.016 (6)
C1B	0.059 (8)	0.081 (8)	0.056 (9)	−0.020 (6)	0.017 (6)	−0.021 (7)
C20B	0.046 (5)	0.075 (5)	0.044 (6)	−0.003 (3)	0.006 (4)	−0.004 (4)
C21B	0.13 (2)	0.111 (18)	0.075 (15)	−0.037 (15)	0.054 (14)	−0.016 (13)

Geometric parameters (Å, º)

C2—C3	1.390 (6)	C15—H15	0.9300
C2—C7	1.395 (6)	C16—C17	1.392 (6)
C2—C20B	1.45 (10)	C16—H16	0.9300
C2—C1A	1.54 (5)	C17—C18	1.388 (6)
C3—C4	1.380 (6)	C17—C1B	1.47 (10)
C3—H3	0.9300	C17—C20A	1.53 (5)
C4—C5	1.401 (5)	C18—C19	1.374 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.391 (5)	C19—H19	0.9300
C5—C8	1.474 (5)	C1A—H1A1	0.9600
C6—C7	1.384 (6)	C1A—H1A2	0.9600
C6—H6	0.9300	C1A—H1A3	0.9600
C7—H7	0.9300	C20A—C21A	1.41 (5)
C8—C13	1.389 (5)	C20A—H20A	0.9700
C8—C9	1.408 (5)	C20A—H20B	0.9700
C9—C10	1.376 (5)	C21A—H21A	0.9600
C9—H9	0.9300	C21A—H21B	0.9600
C10—C11	1.390 (5)	C21A—H21C	0.9600
C10—H10	0.9300	C1B—H20C	0.9600
C11—C12	1.395 (5)	C1B—H20D	0.9600
C11—C14	1.474 (5)	C1B—H20E	0.9600
C12—F2	1.359 (4)	C20B—C21B	1.44 (8)
C12—C13	1.361 (5)	C20B—H1B1	0.9700
C13—F1	1.365 (4)	C20B—H1B2	0.9700
C14—C15	1.395 (6)	C21B—H21D	0.9600
C14—C19	1.404 (5)	C21B—H21E	0.9600
C15—C16	1.387 (6)	C21B—H21F	0.9600
C3—C2—C7	117.7 (4)	C18—C17—C16	117.0 (4)
C3—C2—C20B	122 (3)	C18—C17—C1B	122 (4)
C7—C2—C20B	120 (3)	C16—C17—C1B	121 (4)
C3—C2—C1A	121.2 (15)	C18—C17—C20A	120.7 (17)
C7—C2—C1A	121.1 (15)	C16—C17—C20A	122.2 (17)
C4—C3—C2	121.3 (4)	C19—C18—C17	122.6 (4)
C4—C3—H3	119.3	C19—C18—H18	118.7
C2—C3—H3	119.3	C17—C18—H18	118.7
C3—C4—C5	121.1 (4)	C18—C19—C14	120.6 (4)
C3—C4—H4	119.4	C18—C19—H19	119.7
C5—C4—H4	119.4	C14—C19—H19	119.7
C6—C5—C4	117.5 (4)	C2—C1A—H1A1	109.5
C6—C5—C8	122.7 (4)	C2—C1A—H1A2	109.5
C4—C5—C8	119.7 (3)	H1A1—C1A—H1A2	109.5
C7—C6—C5	121.2 (4)	C2—C1A—H1A3	109.5
C7—C6—H6	119.4	H1A1—C1A—H1A3	109.5
C5—C6—H6	119.4	H1A2—C1A—H1A3	109.5
C6—C7—C2	121.2 (4)	C21A—C20A—C17	115 (3)
C6—C7—H7	119.4	C21A—C20A—H20A	108.5
C2—C7—H7	119.4	C17—C20A—H20A	108.5
C13—C8—C9	115.5 (4)	C21A—C20A—H20B	108.5
C13—C8—C5	123.1 (4)	C17—C20A—H20B	108.5
C9—C8—C5	121.4 (4)	H20A—C20A—H20B	107.5
C10—C9—C8	121.6 (4)	C20A—C21A—H21A	109.5
C10—C9—H9	119.2	C20A—C21A—H21B	109.5
C8—C9—H9	119.2	H21A—C21A—H21B	109.5
C9—C10—C11	122.4 (4)	C20A—C21A—H21C	109.5
C9—C10—H10	118.8	H21A—C21A—H21C	109.5
C11—C10—H10	118.8	H21B—C21A—H21C	109.5
C10—C11—C12	115.6 (4)	C17—C1B—H20C	109.5
C10—C11—C14	121.6 (4)	C17—C1B—H20D	109.5
C12—C11—C14	122.8 (4)	H20C—C1B—H20D	109.5
F2—C12—C13	117.8 (3)	C17—C1B—H20E	109.5
F2—C12—C11	119.8 (4)	H20C—C1B—H20E	109.5
C13—C12—C11	122.4 (4)	H20D—C1B—H20E	109.5
C12—C13—F1	117.5 (3)	C21B—C20B—C2	117 (6)
C12—C13—C8	122.6 (4)	C21B—C20B—H1B1	108.0
F1—C13—C8	119.8 (4)	C2—C20B—H1B1	108.0
C15—C14—C19	117.1 (4)	C21B—C20B—H1B2	108.0
C15—C14—C11	120.6 (4)	C2—C20B—H1B2	108.0
C19—C14—C11	122.2 (4)	H1B1—C20B—H1B2	107.2
C16—C15—C14	121.5 (4)	C20B—C21B—H21D	109.5
C16—C15—H15	119.3	C20B—C21B—H21E	109.5
C14—C15—H15	119.3	H21D—C21B—H21E	109.5
C15—C16—C17	121.2 (4)	C20B—C21B—H21F	109.5
C15—C16—H16	119.4	H21D—C21B—H21F	109.5
C17—C16—H16	119.4	H21E—C21B—H21F	109.5
C7—C2—C3—C4	−0.7 (6)	F2—C12—C13—C8	176.0 (4)
C20B—C2—C3—C4	179 (5)	C11—C12—C13—C8	−1.8 (6)
C1A—C2—C3—C4	−180 (2)	C9—C8—C13—C12	1.4 (6)
C2—C3—C4—C5	0.2 (6)	C5—C8—C13—C12	−178.5 (4)
C3—C4—C5—C6	0.1 (6)	C9—C8—C13—F1	177.5 (3)
C3—C4—C5—C8	179.9 (4)	C5—C8—C13—F1	−2.4 (6)
C4—C5—C6—C7	0.1 (6)	C10—C11—C14—C15	45.1 (6)
C8—C5—C6—C7	−179.7 (4)	C12—C11—C14—C15	−133.4 (4)
C5—C6—C7—C2	−0.6 (6)	C10—C11—C14—C19	−133.4 (4)
C3—C2—C7—C6	0.9 (6)	C12—C11—C14—C19	48.1 (6)
C20B—C2—C7—C6	−179 (4)	C19—C14—C15—C16	0.4 (6)
C1A—C2—C7—C6	−180 (2)	C11—C14—C15—C16	−178.2 (4)
C6—C5—C8—C13	−46.0 (6)	C14—C15—C16—C17	−0.2 (7)
C4—C5—C8—C13	134.2 (4)	C15—C16—C17—C18	−0.4 (7)
C6—C5—C8—C9	134.1 (4)	C15—C16—C17—C1B	175 (4)
C4—C5—C8—C9	−45.8 (5)	C15—C16—C17—C20A	−176.2 (19)
C13—C8—C9—C10	−1.3 (6)	C16—C17—C18—C19	0.9 (7)
C5—C8—C9—C10	178.7 (4)	C1B—C17—C18—C19	−175 (4)
C8—C9—C10—C11	1.4 (6)	C20A—C17—C18—C19	176.8 (18)
C9—C10—C11—C12	−1.6 (6)	C17—C18—C19—C14	−0.7 (7)
C9—C10—C11—C14	179.8 (4)	C15—C14—C19—C18	0.1 (6)
C10—C11—C12—F2	−176.0 (3)	C11—C14—C19—C18	178.6 (4)
C14—C11—C12—F2	2.6 (6)	C18—C17—C20A—C21A	148 (2)
C10—C11—C12—C13	1.7 (6)	C16—C17—C20A—C21A	−36 (4)
C14—C11—C12—C13	−179.7 (4)	C3—C2—C20B—C21B	28 (9)
F2—C12—C13—F1	−0.2 (5)	C7—C2—C20B—C21B	−152 (5)
C11—C12—C13—F1	−177.9 (3)

2',3'-Difluoro-4,4''-dimethyl-p-terphenyl (1T1)

Crystal data

C20H16F2	Z = 4
Mr = 294.33	F(000) = 616
Triclinic, P1	Dx = 1.362 Mg m^−3
a = 9.221 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.519 (5) Å	Cell parameters from 379 reflections
c = 17.254 (10) Å	θ = 2.8–29.4°
α = 89.34 (4)°	µ = 0.10 mm^−1
β = 86.86 (4)°	T = 173 K
γ = 71.71 (3)°	Prism, colourless
V = 1435.8 (13) Å^3	0.40 × 0.30 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	6478 independent reflections
Radiation source: normal-focus sealed tube	3967 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 9 pixels mm^-1	θmax = 27.6°, θmin = 2.7°
CCD rotation images, thick slices scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −12→12
Tmin = 0.940, Tmax = 0.958	l = −22→22
17577 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.169	w = 1/[σ^2(Fo^2) + (0.0738P)^2 + 0.5221P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6478 reflections	Δρmax = 0.32 e Å^−3
401 parameters	Δρmin = −0.28 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.

Refinement. All data for crystal structure determinations were measured on a Bruker-Nonius Kappa CCD diffractometer equipped with an Oxford Cryostream 700 apparatus, using graphite monochromated Mo Kα radiation (0.71073 Å). Reduction of data and semi-empirical absorption correction were done using SADABS program (Bruker–Nonius, 2002). The structures were solved by direct methods SIR97 program (Altomare et al., 1999) and refined by the full-matrix least-squares method on F² using the SHELXL2015 program (Sheldrick, 2015) with the aid of the program WinGX (Farrugia, 2012). The analysis of the crystal packing was performed using the program Mercury (Macrae et al., 2020) and some calculations were performed using PARST97 (Nardelli, 1983, 1995).

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

	x	y	z	Uiso*/Ueq
C1	1.7500 (3)	0.1687 (3)	0.13979 (17)	0.0355 (7)
H1A	1.765298	0.065749	0.130145	0.053*
H1B	1.781678	0.180607	0.190713	0.053*
H1C	1.809351	0.204827	0.101801	0.053*
C2	1.5832 (3)	0.2546 (3)	0.13463 (14)	0.0259 (6)
C3	1.5373 (3)	0.3988 (3)	0.10925 (15)	0.0270 (6)
H3	1.611194	0.442997	0.094362	0.032*
C4	1.3839 (3)	0.4801 (3)	0.10527 (15)	0.0268 (6)
H4	1.356826	0.577667	0.088532	0.032*
C5	1.2709 (3)	0.4174 (3)	0.12592 (13)	0.0222 (5)
C6	1.3170 (3)	0.2714 (3)	0.15116 (15)	0.0266 (6)
H6	1.243575	0.226246	0.165408	0.032*
C7	1.4707 (3)	0.1923 (3)	0.15534 (15)	0.0279 (6)
H7	1.498507	0.094952	0.172516	0.033*
C8	1.1054 (3)	0.5007 (3)	0.12435 (14)	0.0231 (5)
C9	1.0466 (3)	0.6120 (3)	0.07171 (14)	0.0241 (5)
C10	0.8924 (3)	0.6915 (3)	0.07198 (14)	0.0247 (5)
C11	0.7852 (3)	0.6638 (3)	0.12379 (14)	0.0226 (5)
C12	0.8436 (3)	0.5505 (3)	0.17604 (14)	0.0251 (5)
H12	0.776392	0.526047	0.211849	0.030*
C13	0.9978 (3)	0.4728 (3)	0.17676 (14)	0.0247 (5)
H13	1.030722	0.399156	0.213608	0.030*
C14	0.6195 (3)	0.7494 (3)	0.12550 (14)	0.0225 (5)
C15	0.5444 (3)	0.8026 (3)	0.05850 (14)	0.0258 (6)
H15	0.599436	0.788700	0.010887	0.031*
C16	0.3889 (3)	0.8758 (3)	0.06156 (15)	0.0272 (6)
H16	0.341293	0.911203	0.015927	0.033*
C17	0.3021 (3)	0.8977 (3)	0.13141 (15)	0.0255 (6)
C18	0.3774 (3)	0.8468 (3)	0.19841 (15)	0.0267 (6)
H18	0.322220	0.862207	0.246005	0.032*
C19	0.5335 (3)	0.7733 (3)	0.19596 (14)	0.0247 (5)
H19	0.581286	0.739653	0.241756	0.030*
C20	0.1317 (3)	0.9734 (3)	0.13327 (17)	0.0337 (6)
H20A	0.081330	0.903179	0.120309	0.051*
H20B	0.108900	1.052502	0.096351	0.051*
H20C	0.096341	1.012567	0.184337	0.051*
C21	1.2803 (3)	0.1580 (3)	0.36439 (16)	0.0337 (6)
H21A	1.293298	0.054200	0.369149	0.051*
H21B	1.328573	0.188959	0.405944	0.051*
H21C	1.326140	0.176075	0.315558	0.051*
C22	1.1121 (3)	0.2438 (3)	0.36833 (14)	0.0251 (6)
C23	1.0040 (3)	0.1793 (3)	0.34818 (14)	0.0260 (6)
H23	1.035606	0.081184	0.331614	0.031*
C24	0.8494 (3)	0.2587 (3)	0.35231 (14)	0.0246 (5)
H24	0.778921	0.212542	0.339107	0.030*
C25	0.7977 (3)	0.4068 (3)	0.37596 (13)	0.0212 (5)
C26	0.9068 (3)	0.4717 (3)	0.39619 (14)	0.0242 (5)
H26	0.875764	0.570081	0.412183	0.029*
C27	1.0600 (3)	0.3915 (3)	0.39272 (14)	0.0261 (6)
H27	1.130520	0.436765	0.406965	0.031*
C28	0.6318 (3)	0.4894 (3)	0.37710 (14)	0.0225 (5)
C29	0.5352 (3)	0.4555 (3)	0.32559 (14)	0.0261 (6)
H29	0.576554	0.378216	0.290376	0.031*
C30	0.3812 (3)	0.5321 (3)	0.32501 (14)	0.0250 (5)
H30	0.322181	0.503732	0.290072	0.030*
C31	0.3104 (3)	0.6518 (3)	0.37546 (13)	0.0220 (5)
C32	0.4065 (3)	0.6855 (3)	0.42645 (14)	0.0241 (5)
C33	0.5601 (3)	0.6076 (3)	0.42782 (14)	0.0232 (5)
C34	0.1451 (3)	0.7352 (3)	0.37276 (14)	0.0226 (5)
C35	0.0732 (3)	0.7493 (3)	0.30292 (14)	0.0250 (5)
H35	0.129956	0.708660	0.257810	0.030*
C36	−0.0829 (3)	0.8236 (3)	0.29973 (15)	0.0274 (6)
H36	−0.128603	0.831898	0.252434	0.033*
C37	−0.1711 (3)	0.8852 (3)	0.36577 (15)	0.0260 (6)
C38	−0.0989 (3)	0.8719 (3)	0.43528 (15)	0.0267 (6)
H38	−0.156049	0.912968	0.480224	0.032*
C39	0.0558 (3)	0.7990 (3)	0.43925 (14)	0.0249 (5)
H39	0.101175	0.792291	0.486565	0.030*
C40	−0.3408 (3)	0.9619 (3)	0.36335 (18)	0.0352 (7)
H40A	−0.394729	0.892165	0.375180	0.053*
H40B	−0.364193	1.001481	0.312462	0.053*
H40C	−0.371653	1.040806	0.400877	0.053*
F1	1.13707 (17)	0.64703 (17)	0.01622 (9)	0.0359 (4)
F2	0.85046 (17)	0.80071 (17)	0.01980 (9)	0.0359 (4)
F3	0.63900 (17)	0.64922 (17)	0.48250 (9)	0.0344 (4)
F4	0.35327 (17)	0.80082 (17)	0.47739 (9)	0.0347 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0299 (15)	0.0354 (16)	0.0374 (16)	−0.0042 (12)	−0.0048 (12)	−0.0004 (12)
C2	0.0278 (14)	0.0258 (14)	0.0220 (13)	−0.0052 (11)	−0.0022 (10)	−0.0045 (10)
C3	0.0251 (14)	0.0266 (14)	0.0304 (14)	−0.0097 (11)	−0.0007 (10)	−0.0022 (10)
C4	0.0318 (15)	0.0178 (12)	0.0306 (14)	−0.0076 (10)	−0.0014 (11)	−0.0017 (10)
C5	0.0248 (13)	0.0204 (12)	0.0198 (12)	−0.0046 (10)	−0.0019 (9)	−0.0028 (9)
C6	0.0298 (14)	0.0215 (13)	0.0291 (14)	−0.0091 (10)	−0.0009 (10)	0.0003 (10)
C7	0.0328 (15)	0.0198 (13)	0.0287 (14)	−0.0044 (11)	−0.0041 (11)	0.0009 (10)
C8	0.0276 (14)	0.0180 (12)	0.0235 (12)	−0.0066 (10)	−0.0031 (10)	−0.0034 (9)
C9	0.0274 (14)	0.0240 (13)	0.0216 (12)	−0.0101 (10)	0.0037 (10)	−0.0012 (10)
C10	0.0311 (14)	0.0187 (12)	0.0231 (13)	−0.0056 (10)	−0.0048 (10)	0.0045 (10)
C11	0.0267 (13)	0.0191 (12)	0.0220 (12)	−0.0067 (10)	−0.0028 (10)	−0.0031 (9)
C12	0.0279 (14)	0.0241 (13)	0.0246 (13)	−0.0105 (11)	0.0000 (10)	0.0006 (10)
C13	0.0318 (14)	0.0204 (13)	0.0221 (12)	−0.0083 (10)	−0.0030 (10)	0.0037 (10)
C14	0.0254 (13)	0.0159 (12)	0.0253 (13)	−0.0052 (10)	−0.0005 (10)	−0.0011 (9)
C15	0.0281 (14)	0.0230 (13)	0.0238 (13)	−0.0050 (10)	0.0017 (10)	−0.0019 (10)
C16	0.0310 (14)	0.0232 (13)	0.0254 (13)	−0.0055 (11)	−0.0040 (10)	0.0003 (10)
C17	0.0286 (14)	0.0143 (12)	0.0339 (14)	−0.0073 (10)	0.0010 (11)	−0.0018 (10)
C18	0.0323 (15)	0.0225 (13)	0.0251 (13)	−0.0090 (11)	0.0034 (10)	−0.0006 (10)
C19	0.0313 (14)	0.0203 (12)	0.0228 (12)	−0.0080 (10)	−0.0030 (10)	0.0003 (10)
C20	0.0272 (15)	0.0294 (15)	0.0426 (16)	−0.0068 (11)	0.0016 (12)	0.0028 (12)
C21	0.0275 (15)	0.0318 (15)	0.0363 (15)	−0.0015 (11)	0.0005 (11)	−0.0011 (12)
C22	0.0268 (14)	0.0230 (13)	0.0223 (13)	−0.0036 (10)	0.0005 (10)	0.0023 (10)
C23	0.0325 (15)	0.0172 (12)	0.0257 (13)	−0.0044 (10)	0.0002 (10)	−0.0024 (10)
C24	0.0278 (14)	0.0208 (13)	0.0258 (13)	−0.0081 (10)	−0.0026 (10)	−0.0005 (10)
C25	0.0217 (13)	0.0193 (12)	0.0211 (12)	−0.0041 (10)	−0.0018 (9)	0.0020 (9)
C26	0.0298 (14)	0.0145 (12)	0.0271 (13)	−0.0053 (10)	−0.0023 (10)	0.0001 (9)
C27	0.0258 (14)	0.0253 (13)	0.0291 (13)	−0.0104 (10)	−0.0028 (10)	0.0019 (10)
C28	0.0263 (13)	0.0187 (12)	0.0220 (12)	−0.0066 (10)	−0.0005 (10)	0.0024 (9)
C29	0.0324 (15)	0.0205 (13)	0.0235 (13)	−0.0058 (11)	0.0011 (10)	−0.0045 (10)
C30	0.0292 (14)	0.0232 (13)	0.0233 (12)	−0.0086 (10)	−0.0036 (10)	−0.0016 (10)
C31	0.0272 (13)	0.0188 (12)	0.0208 (12)	−0.0084 (10)	−0.0016 (10)	0.0016 (9)
C32	0.0307 (14)	0.0153 (12)	0.0238 (13)	−0.0040 (10)	0.0012 (10)	−0.0046 (9)
C33	0.0260 (13)	0.0209 (13)	0.0243 (13)	−0.0089 (10)	−0.0043 (10)	−0.0027 (10)
C34	0.0271 (13)	0.0165 (12)	0.0246 (13)	−0.0070 (10)	−0.0029 (10)	0.0017 (9)
C35	0.0305 (14)	0.0228 (13)	0.0240 (13)	−0.0118 (11)	0.0005 (10)	−0.0033 (10)
C36	0.0311 (15)	0.0255 (14)	0.0291 (14)	−0.0127 (11)	−0.0095 (11)	0.0023 (10)
C37	0.0254 (13)	0.0176 (12)	0.0358 (14)	−0.0076 (10)	−0.0041 (11)	0.0021 (10)
C38	0.0280 (14)	0.0222 (13)	0.0285 (13)	−0.0067 (10)	0.0025 (10)	0.0008 (10)
C39	0.0304 (14)	0.0201 (13)	0.0226 (13)	−0.0055 (10)	−0.0026 (10)	0.0004 (10)
C40	0.0263 (15)	0.0303 (15)	0.0482 (17)	−0.0069 (11)	−0.0072 (12)	−0.0018 (12)
F1	0.0310 (9)	0.0379 (9)	0.0354 (9)	−0.0075 (7)	0.0053 (6)	0.0132 (7)
F2	0.0324 (9)	0.0320 (9)	0.0392 (9)	−0.0051 (7)	0.0002 (7)	0.0189 (7)
F3	0.0303 (9)	0.0326 (9)	0.0376 (9)	−0.0043 (7)	−0.0093 (7)	−0.0147 (7)
F4	0.0322 (9)	0.0279 (8)	0.0399 (9)	−0.0025 (7)	−0.0041 (7)	−0.0176 (7)

Geometric parameters (Å, º)

C1—C2	1.505 (4)	C21—C22	1.507 (4)
C1—H1A	0.9600	C21—H21A	0.9600
C1—H1B	0.9600	C21—H21B	0.9600
C1—H1C	0.9600	C21—H21C	0.9600
C2—C7	1.377 (4)	C22—C23	1.385 (4)
C2—C3	1.378 (4)	C22—C27	1.397 (4)
C3—C4	1.388 (4)	C23—C24	1.387 (4)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.383 (4)	C24—C25	1.397 (3)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.392 (3)	C25—C26	1.396 (4)
C5—C8	1.484 (3)	C25—C28	1.484 (3)
C6—C7	1.386 (4)	C26—C27	1.377 (3)
C6—H6	0.9300	C26—H26	0.9300
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.383 (3)	C28—C29	1.400 (4)
C8—C13	1.391 (3)	C28—C33	1.400 (4)
C9—F1	1.343 (3)	C29—C30	1.378 (4)
C9—C10	1.385 (4)	C29—H29	0.9300
C10—F2	1.343 (3)	C30—C31	1.406 (3)
C10—C11	1.382 (4)	C30—H30	0.9300
C11—C12	1.390 (3)	C31—C32	1.390 (4)
C11—C14	1.487 (3)	C31—C34	1.485 (3)
C12—C13	1.382 (4)	C32—F4	1.362 (3)
C12—H12	0.9300	C32—C33	1.379 (3)
C13—H13	0.9300	C33—F3	1.357 (3)
C14—C15	1.388 (4)	C34—C35	1.392 (3)
C14—C19	1.395 (3)	C34—C39	1.400 (4)
C15—C16	1.382 (4)	C35—C36	1.394 (4)
C15—H15	0.9300	C35—H35	0.9300
C16—C17	1.390 (4)	C36—C37	1.385 (4)
C16—H16	0.9300	C36—H36	0.9300
C17—C18	1.384 (4)	C37—C38	1.389 (4)
C17—C20	1.508 (4)	C37—C40	1.508 (4)
C18—C19	1.388 (4)	C38—C39	1.382 (4)
C18—H18	0.9300	C38—H38	0.9300
C19—H19	0.9300	C39—H39	0.9300
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600
C2—C1—H1A	109.5	C22—C21—H21A	109.5
C2—C1—H1B	109.5	C22—C21—H21B	109.5
H1A—C1—H1B	109.5	H21A—C21—H21B	109.5
C2—C1—H1C	109.5	C22—C21—H21C	109.5
H1A—C1—H1C	109.5	H21A—C21—H21C	109.5
H1B—C1—H1C	109.5	H21B—C21—H21C	109.5
C7—C2—C3	117.5 (2)	C23—C22—C27	117.7 (2)
C7—C2—C1	121.3 (2)	C23—C22—C21	121.4 (2)
C3—C2—C1	121.2 (2)	C27—C22—C21	120.9 (2)
C2—C3—C4	121.8 (2)	C22—C23—C24	121.0 (2)
C2—C3—H3	119.1	C22—C23—H23	119.5
C4—C3—H3	119.1	C24—C23—H23	119.5
C5—C4—C3	120.7 (2)	C23—C24—C25	121.1 (2)
C5—C4—H4	119.7	C23—C24—H24	119.4
C3—C4—H4	119.7	C25—C24—H24	119.4
C4—C5—C6	117.6 (2)	C26—C25—C24	117.7 (2)
C4—C5—C8	122.7 (2)	C26—C25—C28	122.7 (2)
C6—C5—C8	119.7 (2)	C24—C25—C28	119.5 (2)
C7—C6—C5	120.9 (2)	C27—C26—C25	120.7 (2)
C7—C6—H6	119.5	C27—C26—H26	119.6
C5—C6—H6	119.5	C25—C26—H26	119.6
C2—C7—C6	121.5 (2)	C26—C27—C22	121.6 (2)
C2—C7—H7	119.3	C26—C27—H27	119.2
C6—C7—H7	119.3	C22—C27—H27	119.2
C9—C8—C13	115.0 (2)	C29—C28—C33	114.9 (2)
C9—C8—C5	123.0 (2)	C29—C28—C25	121.7 (2)
C13—C8—C5	122.0 (2)	C33—C28—C25	123.4 (2)
F1—C9—C8	121.2 (2)	C30—C29—C28	122.6 (2)
F1—C9—C10	116.2 (2)	C30—C29—H29	118.7
C8—C9—C10	122.5 (2)	C28—C29—H29	118.7
F2—C10—C11	120.5 (2)	C29—C30—C31	122.2 (2)
F2—C10—C9	116.8 (2)	C29—C30—H30	118.9
C11—C10—C9	122.6 (2)	C31—C30—H30	118.9
C10—C11—C12	115.0 (2)	C32—C31—C30	115.1 (2)
C10—C11—C14	123.3 (2)	C32—C31—C34	123.5 (2)
C12—C11—C14	121.7 (2)	C30—C31—C34	121.4 (2)
C13—C12—C11	122.5 (2)	F4—C32—C33	116.1 (2)
C13—C12—H12	118.8	F4—C32—C31	121.1 (2)
C11—C12—H12	118.8	C33—C32—C31	122.8 (2)
C12—C13—C8	122.4 (2)	F3—C33—C32	116.4 (2)
C12—C13—H13	118.8	F3—C33—C28	121.1 (2)
C8—C13—H13	118.8	C32—C33—C28	122.4 (2)
C15—C14—C19	118.0 (2)	C35—C34—C39	117.8 (2)
C15—C14—C11	122.2 (2)	C35—C34—C31	120.1 (2)
C19—C14—C11	119.8 (2)	C39—C34—C31	122.1 (2)
C16—C15—C14	120.9 (2)	C34—C35—C36	120.8 (2)
C16—C15—H15	119.5	C34—C35—H35	119.6
C14—C15—H15	119.5	C36—C35—H35	119.6
C15—C16—C17	121.4 (2)	C37—C36—C35	121.1 (2)
C15—C16—H16	119.3	C37—C36—H36	119.4
C17—C16—H16	119.3	C35—C36—H36	119.4
C18—C17—C16	117.7 (2)	C36—C37—C38	117.9 (2)
C18—C17—C20	121.7 (2)	C36—C37—C40	121.5 (2)
C16—C17—C20	120.6 (2)	C38—C37—C40	120.5 (2)
C17—C18—C19	121.3 (2)	C39—C38—C37	121.6 (2)
C17—C18—H18	119.3	C39—C38—H38	119.2
C19—C18—H18	119.3	C37—C38—H38	119.2
C18—C19—C14	120.7 (2)	C38—C39—C34	120.7 (2)
C18—C19—H19	119.7	C38—C39—H39	119.7
C14—C19—H19	119.7	C34—C39—H39	119.7
C17—C20—H20A	109.5	C37—C40—H40A	109.5
C17—C20—H20B	109.5	C37—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
C17—C20—H20C	109.5	C37—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5
C7—C2—C3—C4	0.7 (4)	C27—C22—C23—C24	−0.2 (4)
C1—C2—C3—C4	−179.0 (3)	C21—C22—C23—C24	179.7 (2)
C2—C3—C4—C5	−0.9 (4)	C22—C23—C24—C25	0.8 (4)
C3—C4—C5—C6	0.5 (4)	C23—C24—C25—C26	−0.8 (3)
C3—C4—C5—C8	178.6 (2)	C23—C24—C25—C28	178.0 (2)
C4—C5—C6—C7	0.0 (4)	C24—C25—C26—C27	0.0 (3)
C8—C5—C6—C7	−178.1 (2)	C28—C25—C26—C27	−178.6 (2)
C3—C2—C7—C6	−0.2 (4)	C25—C26—C27—C22	0.6 (4)
C1—C2—C7—C6	179.6 (2)	C23—C22—C27—C26	−0.6 (4)
C5—C6—C7—C2	−0.2 (4)	C21—C22—C27—C26	179.6 (2)
C4—C5—C8—C9	31.8 (4)	C26—C25—C28—C29	148.9 (2)
C6—C5—C8—C9	−150.1 (3)	C24—C25—C28—C29	−29.7 (3)
C4—C5—C8—C13	−147.5 (3)	C26—C25—C28—C33	−29.8 (4)
C6—C5—C8—C13	30.6 (4)	C24—C25—C28—C33	151.5 (2)
C13—C8—C9—F1	−177.7 (2)	C33—C28—C29—C30	−0.3 (4)
C5—C8—C9—F1	2.8 (4)	C25—C28—C29—C30	−179.1 (2)
C13—C8—C9—C10	1.1 (4)	C28—C29—C30—C31	1.1 (4)
C5—C8—C9—C10	−178.3 (2)	C29—C30—C31—C32	−0.9 (3)
F1—C9—C10—F2	−3.6 (3)	C29—C30—C31—C34	178.6 (2)
C8—C9—C10—F2	177.5 (2)	C30—C31—C32—F4	178.7 (2)
F1—C9—C10—C11	177.5 (2)	C34—C31—C32—F4	−0.8 (4)
C8—C9—C10—C11	−1.3 (4)	C30—C31—C32—C33	0.0 (4)
F2—C10—C11—C12	−178.5 (2)	C34—C31—C32—C33	−179.5 (2)
C9—C10—C11—C12	0.3 (4)	F4—C32—C33—F3	3.5 (3)
F2—C10—C11—C14	0.4 (4)	C31—C32—C33—F3	−177.7 (2)
C9—C10—C11—C14	179.2 (2)	F4—C32—C33—C28	−177.9 (2)
C10—C11—C12—C13	0.9 (4)	C31—C32—C33—C28	0.8 (4)
C14—C11—C12—C13	−178.0 (2)	C29—C28—C33—F3	177.8 (2)
C11—C12—C13—C8	−1.1 (4)	C25—C28—C33—F3	−3.4 (4)
C9—C8—C13—C12	0.1 (4)	C29—C28—C33—C32	−0.7 (4)
C5—C8—C13—C12	179.5 (2)	C25—C28—C33—C32	178.2 (2)
C10—C11—C14—C15	35.3 (4)	C32—C31—C34—C35	148.7 (2)
C12—C11—C14—C15	−145.8 (3)	C30—C31—C34—C35	−30.8 (3)
C10—C11—C14—C19	−147.2 (3)	C32—C31—C34—C39	−32.7 (4)
C12—C11—C14—C19	31.7 (4)	C30—C31—C34—C39	147.9 (2)
C19—C14—C15—C16	−0.5 (4)	C39—C34—C35—C36	−0.5 (4)
C11—C14—C15—C16	177.0 (2)	C31—C34—C35—C36	178.2 (2)
C14—C15—C16—C17	−0.6 (4)	C34—C35—C36—C37	−0.1 (4)
C15—C16—C17—C18	1.6 (4)	C35—C36—C37—C38	0.6 (4)
C15—C16—C17—C20	−177.9 (2)	C35—C36—C37—C40	−178.2 (2)
C16—C17—C18—C19	−1.5 (4)	C36—C37—C38—C39	−0.3 (4)
C20—C17—C18—C19	178.0 (2)	C40—C37—C38—C39	178.5 (2)
C17—C18—C19—C14	0.4 (4)	C37—C38—C39—C34	−0.3 (4)
C15—C14—C19—C18	0.6 (4)	C35—C34—C39—C38	0.8 (4)
C11—C14—C19—C18	−177.0 (2)	C31—C34—C39—C38	−177.9 (2)