Influence of fluoro-substitution on the planarity of 4-chlorobiphenyl (PCB 3)

Accurate structure determinations by X-ray crystal analysis and computation using semi-empirical self-consistent field molecular orbital calculations are described and compared for five monofluorinated analogues of 4-chlorobiphenyl, i.e. 2-fluoro-4-chlorobiphenyl, 2′-fluoro-4-chlorobiphenyl, 3-fluoro-4-chlorobiphenyl, 3′-fluoro-4-chlorobiphenyl and 4′-fluoro-4-chlorobiphenyl. Intermolecular interactions for all monofluorinated isomers are dominated by phenyl–phenyl stacking and C—H–phenyl interactions. C—F bond lengths varied between 1.341 and 1.374 Å, C—Cl between 1.733 and 1.765 Å, and both correlate with electron-density differences as determined by ¹³C NMR shifts. The interior ring angles at ipso-fluoro substitution increase up to 122.2–124.2° due to hyperconjugation by 2p-π-orbital overlapping, a phenomenon that was also reflected in the computer calculation. The angles of C—F and C—Cl relative to the aromatic ring for vicinal fluoro- and chloro substituents show an attraction, not a repulsion, between the adjacent F and Cl substituents. This finding is explained on the basis of electron donor and acceptor properties. The dihedral angles of ortho-substituted biphenyls show that monofluoro substitution results in slightly smaller increases compared with chlorine, while additional ortho-fluorination results in little further change in the dihedral angle. In contrast, ortho-chlorination strongly decreases the co-planarity. This is likely to be due to interior ring-angle distortion and the size of the halogen substituent. Fluoro substitution does indeed affect the planarity of the PCB3 analogues, but these effects are minor compared with chloro substitution. Fluorine tagging offers promise for use in in vitro and in vivo studies. Differences in computational versus measured data emphasize the need to use a variety of methods to ascertain the true nature of the physical properties of a compound.

Computing details

Data collection: Collect (Nonius BV, 1997-2000) for 3F-PCB3, 3'F-PCB3, 4'F-PCB3; Collect (Nonius BV, 1997 - 2000) for 2F-PCB3, 2'F-PCB3. For all compounds, cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997). Data reduction: HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997) for 3F-PCB3, 2F-PCB3, 3'F-PCB3, 4'F-PCB3; HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997 for 2'F-PCB3. Program(s) used to solve structure: SHELXTL v6.1 (Sheldrick, 2001) for 3F-PCB3, 2F-PCB3, 2'F-PCB3, 4'F-PCB3; SHELXTL v6.1 (Sheldrick, 1997) for 3'F-PCB3. Program(s) used to refine structure: SHELXTL v6.1 (Sheldrick, 2001) for 3F-PCB3, 2F-PCB3, 2'F-PCB3, 4'F-PCB3; SHELXTL v6.1 (Sheldrick, 1997) for 3'F-PCB3. Molecular graphics: SHELXTL v6.1 (Sheldrick, 2001) for 3F-PCB3, 2F-PCB3, 2'F-PCB3, 4'F-PCB3; SHELXTL v6.1 (Sheldrick, 1997) for 3'F-PCB3. Software used to prepare material for publication: SHELXTL v6.1 (Sheldrick, 2001) for 3F-PCB3, 2F-PCB3, 2'F-PCB3, 4'F-PCB3; SHELXTL v6.1 (Sheldrick, 1997) for 3'F-PCB3.

Figures

(3F-PCB3)

Crystal data

C12H8ClF	F(000) = 848
Mr = 206.63	Dx = 1.432 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8130 reflections
a = 11.9836 (7) Å	θ = 1.0–27.5°
b = 7.3820 (12) Å	µ = 0.36 mm^−1
c = 21.670 (2) Å	T = 190 K
V = 1917.0 (4) Å^3	Needle, colorless
Z = 8	0.35 × 0.08 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer	1691 independent reflections
Radiation source: fine-focus sealed tube	1367 reflections with I > 2u(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 9 pixels mm^-1	θmax = 25.0°, θmin = 3.4°
CCD ϕ and ω scans	h = −14→14
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −8→8
Tmin = 0.883, Tmax = 0.975	l = −25→25
34729 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0686P)^2 + 2.4606P] where P = (Fo^2 + 2Fc^2)/3
1691 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.30 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1	0.17083 (7)	0.54259 (12)	0.56951 (3)	0.0495 (3)
F1	0.40076 (16)	0.5729 (3)	0.53112 (8)	0.0579 (6)
C1	0.2982 (2)	0.7029 (3)	0.38027 (12)	0.0268 (6)
C2	0.3717 (2)	0.6615 (4)	0.42809 (12)	0.0320 (6)
H2	0.4499	0.6655	0.4213	0.038*
C3	0.3306 (2)	0.6151 (4)	0.48510 (12)	0.0342 (7)
C4	0.2180 (3)	0.6069 (4)	0.49715 (12)	0.0339 (7)
C5	0.1442 (3)	0.6499 (4)	0.45078 (14)	0.0366 (7)
H5	0.0662	0.6469	0.4584	0.044*
C6	0.1836 (2)	0.6975 (4)	0.39297 (12)	0.0302 (6)
H6	0.1320	0.7271	0.3613	0.036*
C1'	0.3390 (2)	0.7495 (3)	0.31739 (12)	0.0260 (6)
C2'	0.4402 (2)	0.8379 (4)	0.30811 (13)	0.0319 (6)
H2'	0.4855	0.8676	0.3426	0.038*
C3'	0.4761 (3)	0.8832 (4)	0.24931 (15)	0.0381 (7)
H3'	0.5455	0.9431	0.2438	0.046*
C4'	0.4106 (3)	0.8412 (4)	0.19855 (14)	0.0395 (7)
H4'	0.4346	0.8738	0.1583	0.047*
C5'	0.3103 (2)	0.7518 (4)	0.20684 (13)	0.0362 (7)
H5'	0.2657	0.7219	0.1721	0.043*
C6'	0.2746 (2)	0.7056 (4)	0.26532 (12)	0.0306 (6)
H6'	0.2058	0.6435	0.2704	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0624 (6)	0.0567 (6)	0.0293 (4)	−0.0053 (4)	0.0090 (3)	0.0020 (3)
F1	0.0512 (12)	0.0833 (15)	0.0393 (10)	0.0104 (10)	−0.0075 (9)	0.0098 (10)
C1	0.0313 (14)	0.0202 (13)	0.0288 (14)	0.0002 (11)	−0.0024 (11)	−0.0027 (11)
C2	0.0309 (14)	0.0316 (15)	0.0334 (15)	0.0010 (12)	−0.0014 (12)	−0.0008 (12)
C3	0.0431 (17)	0.0336 (16)	0.0261 (14)	0.0041 (12)	−0.0086 (12)	0.0000 (12)
C4	0.0459 (18)	0.0289 (15)	0.0268 (14)	−0.0034 (13)	0.0052 (13)	−0.0026 (11)
C5	0.0385 (16)	0.0357 (16)	0.0355 (15)	−0.0013 (13)	0.0026 (13)	−0.0037 (13)
C6	0.0299 (14)	0.0306 (15)	0.0301 (14)	0.0007 (11)	−0.0027 (11)	−0.0007 (12)
C1'	0.0260 (13)	0.0230 (14)	0.0289 (14)	0.0033 (10)	0.0004 (11)	−0.0005 (11)
C2'	0.0304 (14)	0.0289 (15)	0.0363 (15)	0.0006 (12)	−0.0031 (12)	−0.0004 (12)
C3'	0.0353 (16)	0.0329 (16)	0.0460 (16)	−0.0005 (13)	0.0101 (14)	0.0030 (13)
C4'	0.0499 (18)	0.0367 (17)	0.0319 (15)	0.0074 (14)	0.0098 (13)	0.0055 (13)
C5'	0.0453 (17)	0.0374 (17)	0.0259 (14)	0.0062 (13)	−0.0039 (13)	−0.0029 (12)
C6'	0.0331 (15)	0.0277 (14)	0.0310 (14)	0.0002 (12)	−0.0021 (11)	−0.0004 (11)

Geometric parameters (Å, º)

Cl1—C4	1.733 (3)	C1'—C2'	1.392 (4)
F1—C3	1.341 (3)	C1'—C6'	1.404 (4)
C1—C2	1.394 (4)	C2'—C3'	1.386 (4)
C1—C6	1.400 (4)	C2'—H2'	0.9500
C1—C1'	1.488 (4)	C3'—C4'	1.386 (4)
C2—C3	1.373 (4)	C3'—H3'	0.9500
C2—H2	0.9500	C4'—C5'	1.383 (4)
C3—C4	1.377 (4)	C4'—H4'	0.9500
C4—C5	1.375 (4)	C5'—C6'	1.380 (4)
C5—C6	1.384 (4)	C5'—H5'	0.9500
C5—H5	0.9500	C6'—H6'	0.9500
C6—H6	0.9500
C2—C1—C6	117.8 (2)	C2'—C1'—C6'	118.1 (2)
C2—C1—C1'	121.6 (2)	C2'—C1'—C1	121.8 (2)
C6—C1—C1'	120.6 (2)	C6'—C1'—C1	120.1 (2)
C3—C2—C1	119.8 (3)	C3'—C2'—C1'	121.1 (3)
C3—C2—H2	120.1	C3'—C2'—H2'	119.5
C1—C2—H2	120.1	C1'—C2'—H2'	119.5
F1—C3—C2	120.2 (3)	C2'—C3'—C4'	120.0 (3)
F1—C3—C4	117.6 (2)	C2'—C3'—H3'	120.0
C2—C3—C4	122.2 (3)	C4'—C3'—H3'	120.0
C5—C4—C3	118.8 (3)	C5'—C4'—C3'	119.7 (3)
C5—C4—Cl1	121.0 (2)	C5'—C4'—H4'	120.2
C3—C4—Cl1	120.2 (2)	C3'—C4'—H4'	120.2
C4—C5—C6	120.1 (3)	C6'—C5'—C4'	120.4 (3)
C4—C5—H5	120.0	C6'—C5'—H5'	119.8
C6—C5—H5	120.0	C4'—C5'—H5'	119.8
C5—C6—C1	121.3 (3)	C5'—C6'—C1'	120.7 (3)
C5—C6—H6	119.4	C5'—C6'—H6'	119.6
C1—C6—H6	119.4	C1'—C6'—H6'	119.6
C6—C1—C2—C3	0.9 (4)	C2—C1—C1'—C2'	−31.5 (4)
C1'—C1—C2—C3	−178.5 (2)	C6—C1—C1'—C2'	149.1 (3)
C1—C2—C3—F1	179.1 (2)	C2—C1—C1'—C6'	148.9 (3)
C1—C2—C3—C4	0.2 (4)	C6—C1—C1'—C6'	−30.5 (4)
F1—C3—C4—C5	179.8 (3)	C6'—C1'—C2'—C3'	0.7 (4)
C2—C3—C4—C5	−1.2 (4)	C1—C1'—C2'—C3'	−178.9 (2)
F1—C3—C4—Cl1	−0.4 (4)	C1'—C2'—C3'—C4'	0.2 (4)
C2—C3—C4—Cl1	178.6 (2)	C2'—C3'—C4'—C5'	−0.9 (4)
C3—C4—C5—C6	1.1 (4)	C3'—C4'—C5'—C6'	0.6 (4)
Cl1—C4—C5—C6	−178.8 (2)	C4'—C5'—C6'—C1'	0.4 (4)
C4—C5—C6—C1	0.1 (4)	C2'—C1'—C6'—C5'	−1.1 (4)
C2—C1—C6—C5	−1.1 (4)	C1—C1'—C6'—C5'	178.5 (2)
C1'—C1—C6—C5	178.4 (2)

(2F-PCB3)

Crystal data

C12H8ClF	F(000) = 848
Mr = 206.63	Dx = 1.431 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 4148 reflections
a = 17.4184 (17) Å	θ = 1.0–27.5°
b = 5.8649 (6) Å	µ = 0.36 mm^−1
c = 19.4400 (19) Å	T = 190 K
β = 104.981 (5)°	Prism, colorless
V = 1918.4 (3) Å^3	0.38 × 0.36 × 0.30 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2u(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.7°
CCD ϕ and ω scans	h = −22→22
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −7→7
Tmin = 0.874, Tmax = 0.899	l = −25→25
18886 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 1.2786P] where P = (Fo^2 + 2Fc^2)/3
2192 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.25 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1	0.534569 (19)	0.53910 (7)	0.664773 (16)	0.04228 (13)
F1	0.38354 (5)	0.86166 (13)	0.42927 (4)	0.0375 (2)
C1	0.33888 (6)	0.50333 (19)	0.45940 (6)	0.0233 (2)
C2	0.39030 (7)	0.6877 (2)	0.47656 (6)	0.0259 (2)
C3	0.45045 (7)	0.7040 (2)	0.53856 (6)	0.0287 (3)
H3	0.4842	0.8337	0.5483	0.034*
C4	0.45969 (7)	0.5239 (2)	0.58602 (6)	0.0281 (3)
C5	0.41148 (7)	0.3337 (2)	0.57200 (6)	0.0295 (3)
H5	0.4189	0.2112	0.6050	0.035*
C6	0.35197 (7)	0.3248 (2)	0.50875 (6)	0.0263 (2)
H6	0.3191	0.1932	0.4987	0.032*
C1'	0.27271 (7)	0.49392 (19)	0.39327 (6)	0.0234 (2)
C2'	0.21743 (7)	0.6710 (2)	0.37611 (6)	0.0281 (3)
H2'	0.2232	0.8018	0.4058	0.034*
C3'	0.15408 (7)	0.6569 (2)	0.31581 (6)	0.0318 (3)
H3'	0.1165	0.7776	0.3047	0.038*
C4'	0.14543 (7)	0.4679 (2)	0.27168 (6)	0.0318 (3)
H4'	0.1021	0.4591	0.2304	0.038*
C5'	0.20028 (7)	0.2911 (2)	0.28788 (6)	0.0311 (3)
H5'	0.1947	0.1618	0.2576	0.037*
C6'	0.26342 (7)	0.3040 (2)	0.34856 (6)	0.0270 (2)
H6'	0.3006	0.1824	0.3597	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.03151 (18)	0.0647 (3)	0.02510 (17)	0.00510 (15)	−0.00272 (12)	−0.00644 (14)
F1	0.0434 (4)	0.0267 (4)	0.0386 (4)	−0.0016 (3)	0.0039 (3)	0.0083 (3)
C1	0.0226 (5)	0.0261 (6)	0.0214 (5)	0.0041 (4)	0.0060 (4)	−0.0009 (4)
C2	0.0302 (6)	0.0232 (5)	0.0252 (5)	0.0036 (4)	0.0088 (5)	0.0010 (4)
C3	0.0261 (6)	0.0301 (6)	0.0295 (6)	−0.0003 (5)	0.0067 (5)	−0.0064 (5)
C4	0.0231 (5)	0.0399 (7)	0.0205 (5)	0.0059 (5)	0.0044 (4)	−0.0040 (5)
C5	0.0289 (6)	0.0364 (7)	0.0239 (5)	0.0053 (5)	0.0080 (5)	0.0064 (5)
C6	0.0252 (5)	0.0277 (6)	0.0266 (5)	0.0008 (4)	0.0078 (4)	0.0021 (4)
C1'	0.0229 (5)	0.0264 (6)	0.0209 (5)	0.0009 (4)	0.0059 (4)	0.0021 (4)
C2'	0.0304 (6)	0.0288 (6)	0.0249 (5)	0.0057 (5)	0.0067 (5)	−0.0005 (4)
C3'	0.0279 (6)	0.0375 (7)	0.0288 (6)	0.0094 (5)	0.0053 (5)	0.0060 (5)
C4'	0.0278 (6)	0.0406 (7)	0.0240 (6)	−0.0010 (5)	0.0013 (5)	0.0031 (5)
C5'	0.0329 (6)	0.0322 (6)	0.0262 (6)	−0.0029 (5)	0.0041 (5)	−0.0036 (5)
C6'	0.0276 (6)	0.0250 (6)	0.0277 (6)	0.0023 (4)	0.0058 (4)	0.0005 (4)

Geometric parameters (Å, º)

Cl1—C4	1.7381 (12)	C1'—C6'	1.3961 (16)
F1—C2	1.3581 (13)	C1'—C2'	1.3967 (16)
C1—C2	1.3884 (17)	C2'—C3'	1.3891 (16)
C1—C6	1.3986 (16)	C2'—H2'	0.9500
C1—C1'	1.4894 (15)	C3'—C4'	1.3860 (18)
C2—C3	1.3809 (16)	C3'—H3'	0.9500
C3—C4	1.3841 (17)	C4'—C5'	1.3896 (18)
C3—H3	0.9500	C4'—H4'	0.9500
C4—C5	1.3800 (18)	C5'—C6'	1.3914 (16)
C5—C6	1.3892 (16)	C5'—H5'	0.9500
C5—H5	0.9500	C6'—H6'	0.9500
C6—H6	0.9500
C2—C1—C6	115.95 (10)	C6'—C1'—C2'	118.85 (10)
C2—C1—C1'	122.92 (10)	C6'—C1'—C1	120.41 (10)
C6—C1—C1'	121.13 (10)	C2'—C1'—C1	120.70 (10)
F1—C2—C3	116.89 (10)	C3'—C2'—C1'	120.38 (11)
F1—C2—C1	119.00 (10)	C3'—C2'—H2'	119.8
C3—C2—C1	124.08 (11)	C1'—C2'—H2'	119.8
C2—C3—C4	117.40 (11)	C4'—C3'—C2'	120.35 (11)
C2—C3—H3	121.3	C4'—C3'—H3'	119.8
C4—C3—H3	121.3	C2'—C3'—H3'	119.8
C5—C4—C3	121.67 (10)	C3'—C4'—C5'	119.88 (11)
C5—C4—Cl1	119.69 (9)	C3'—C4'—H4'	120.1
C3—C4—Cl1	118.64 (9)	C5'—C4'—H4'	120.1
C4—C5—C6	118.83 (11)	C4'—C5'—C6'	119.87 (11)
C4—C5—H5	120.6	C4'—C5'—H5'	120.1
C6—C5—H5	120.6	C6'—C5'—H5'	120.1
C5—C6—C1	122.05 (11)	C5'—C6'—C1'	120.67 (11)
C5—C6—H6	119.0	C5'—C6'—H6'	119.7
C1—C6—H6	119.0	C1'—C6'—H6'	119.7
C6—C1—C2—F1	176.62 (10)	C2—C1—C1'—C6'	129.38 (12)
C1'—C1—C2—F1	−4.19 (16)	C6—C1—C1'—C6'	−51.48 (15)
C6—C1—C2—C3	−1.39 (17)	C2—C1—C1'—C2'	−52.75 (16)
C1'—C1—C2—C3	177.80 (10)	C6—C1—C1'—C2'	126.40 (12)
F1—C2—C3—C4	−177.77 (10)	C6'—C1'—C2'—C3'	0.45 (17)
C1—C2—C3—C4	0.28 (17)	C1—C1'—C2'—C3'	−177.46 (10)
C2—C3—C4—C5	0.66 (17)	C1'—C2'—C3'—C4'	−0.55 (18)
C2—C3—C4—Cl1	−179.76 (8)	C2'—C3'—C4'—C5'	0.13 (19)
C3—C4—C5—C6	−0.42 (17)	C3'—C4'—C5'—C6'	0.38 (18)
Cl1—C4—C5—C6	−179.99 (9)	C4'—C5'—C6'—C1'	−0.48 (18)
C4—C5—C6—C1	−0.79 (17)	C2'—C1'—C6'—C5'	0.06 (17)
C2—C1—C6—C5	1.63 (16)	C1—C1'—C6'—C5'	177.98 (10)
C1'—C1—C6—C5	−177.57 (10)

(2'F-PCB3)

Crystal data

C12H8ClF	F(000) = 848
Mr = 206.63	Dx = 1.412 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 8447 reflections
a = 17.9426 (18) Å	θ = 1.0–27.5°
b = 6.0863 (6) Å	µ = 0.36 mm^−1
c = 18.3206 (18) Å	T = 190 K
β = 103.701 (5)°	Prism, colorless
V = 1943.8 (3) Å^3	0.44 × 0.38 × 0.30 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	2217 independent reflections
Radiation source: fine-focus sealed tube	1708 reflections with I > 2u(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.6°
CCD ϕ and ω scans	h = −22→23
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −7→7
Tmin = 0.858, Tmax = 0.900	l = −23→23
32179 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.6778P] where P = (Fo^2 + 2Fc^2)/3
2217 reflections	(Δ/σ)max = 0.012
131 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.26 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Late refinement difference maps suggested a minor disorder of 180ο rotation about the >C1 - C1'< bond of the C1' - C6' phenyl ring. The relative occupancy refined to 0.9774 (16):0.0226 (16) with the sum constrained to 1.0. Also U(iso)(F2) = 1.2*U(iso,eq)(C2') and the C2" - F2 was constrained to be the same as C2' - F1.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.10919 (2)	0.43861 (8)	0.22489 (2)	0.05558 (17)
C1	0.30638 (7)	0.5057 (2)	0.42933 (7)	0.0281 (3)
C2	0.25507 (8)	0.6791 (2)	0.40648 (8)	0.0317 (3)
H2	0.2621	0.8127	0.4341	0.038*
C3	0.19403 (8)	0.6592 (2)	0.34411 (8)	0.0359 (3)
H3	0.1590	0.7771	0.3294	0.043*
C4	0.18498 (8)	0.4652 (2)	0.30378 (8)	0.0351 (3)
C5	0.23510 (8)	0.2920 (2)	0.32435 (8)	0.0368 (3)
H5	0.2284	0.1600	0.2959	0.044*
C6	0.29539 (8)	0.3130 (2)	0.38717 (8)	0.0331 (3)
H6	0.3299	0.1937	0.4017	0.040*
C1'	0.36992 (7)	0.5213 (2)	0.49781 (7)	0.0276 (3)
C2'	0.41864 (7)	0.7012 (2)	0.51331 (8)	0.0313 (3)	0.9774 (16)
F1	0.40804 (5)	0.86925 (14)	0.46286 (5)	0.0437 (3)	0.9774 (16)
C3'	0.47819 (8)	0.7193 (2)	0.57597 (8)	0.0398 (4)
H3'	0.5097	0.8466	0.5840	0.048*
C4'	0.49120 (8)	0.5478 (3)	0.62725 (9)	0.0403 (4)
H4'	0.5320	0.5562	0.6709	0.048*
C5'	0.44443 (8)	0.3644 (3)	0.61447 (8)	0.0381 (4)
H5'	0.4532	0.2467	0.6496	0.046*
C6'	0.38487 (8)	0.3512 (2)	0.55077 (8)	0.0333 (3)	0.9774 (16)
H6'	0.3534	0.2237	0.5428	0.040*	0.9774 (16)
C2"	0.38487 (8)	0.3512 (2)	0.55077 (8)	0.0333 (3)	0.0226 (16)
F2	0.3398 (17)	0.169 (3)	0.536 (2)	0.040*	0.0226 (16)
C6"	0.41864 (7)	0.7012 (2)	0.51331 (8)	0.0313 (3)	0.0226 (16)
H6"	0.4103	0.8193	0.4784	0.038*	0.0226 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0481 (3)	0.0746 (3)	0.0349 (2)	−0.0194 (2)	−0.00848 (17)	0.00921 (19)
C1	0.0267 (6)	0.0307 (7)	0.0278 (7)	0.0006 (5)	0.0084 (5)	0.0021 (5)
C2	0.0325 (7)	0.0314 (7)	0.0309 (7)	0.0036 (5)	0.0066 (6)	−0.0001 (6)
C3	0.0307 (7)	0.0407 (8)	0.0356 (8)	0.0047 (6)	0.0067 (6)	0.0084 (6)
C4	0.0315 (7)	0.0461 (9)	0.0261 (6)	−0.0086 (6)	0.0037 (5)	0.0039 (6)
C5	0.0400 (8)	0.0378 (8)	0.0332 (7)	−0.0074 (6)	0.0098 (6)	−0.0067 (6)
C6	0.0333 (7)	0.0297 (7)	0.0372 (7)	0.0010 (6)	0.0100 (6)	−0.0009 (6)
C1'	0.0253 (6)	0.0291 (7)	0.0293 (6)	0.0037 (5)	0.0080 (5)	−0.0005 (5)
C2'	0.0316 (7)	0.0291 (7)	0.0330 (7)	0.0032 (5)	0.0074 (6)	0.0040 (6)
F1	0.0452 (5)	0.0319 (5)	0.0484 (5)	−0.0044 (4)	0.0003 (4)	0.0115 (4)
C3'	0.0321 (7)	0.0415 (8)	0.0441 (8)	−0.0039 (6)	0.0053 (6)	−0.0032 (6)
C4'	0.0295 (7)	0.0536 (10)	0.0344 (7)	0.0025 (6)	0.0009 (6)	0.0034 (7)
C5'	0.0331 (7)	0.0449 (9)	0.0355 (8)	0.0042 (6)	0.0068 (6)	0.0122 (7)
C6'	0.0303 (7)	0.0336 (7)	0.0357 (7)	0.0008 (6)	0.0075 (6)	0.0053 (6)
C2"	0.0303 (7)	0.0336 (7)	0.0357 (7)	0.0008 (6)	0.0075 (6)	0.0053 (6)
C1"	0.0253 (6)	0.0291 (7)	0.0293 (6)	0.0037 (5)	0.0080 (5)	−0.0005 (5)
C6"	0.0316 (7)	0.0291 (7)	0.0330 (7)	0.0032 (5)	0.0074 (6)	0.0040 (6)
C5"	0.0321 (7)	0.0415 (8)	0.0441 (8)	−0.0039 (6)	0.0053 (6)	−0.0032 (6)

Geometric parameters (Å, º)

Cl1—C4	1.7417 (14)	C1'—C2'	1.3879 (19)
C1—C6	1.3922 (19)	C1'—C6'	1.4008 (19)
C1—C2	1.3981 (19)	C2'—F1	1.3613 (15)
C1—C1'	1.4850 (18)	C2'—C3'	1.3750 (19)
C2—C3	1.3881 (18)	C3'—C4'	1.387 (2)
C2—H2	0.9500	C3'—H3'	0.9500
C3—C4	1.382 (2)	C4'—C5'	1.383 (2)
C3—H3	0.9500	C4'—H4'	0.9500
C4—C5	1.379 (2)	C5'—C6'	1.3855 (19)
C5—C6	1.3861 (19)	C5'—H5'	0.9500
C5—H5	0.9500	C6'—H6'	0.9500
C6—H6	0.9500	C2"—F2	1.360
C6—C1—C2	118.23 (12)	C2'—C1'—C6'	115.68 (12)
C6—C1—C1'	120.16 (11)	C2'—C1'—C1	122.94 (12)
C2—C1—C1'	121.59 (12)	C6'—C1'—C1	121.37 (12)
C3—C2—C1	121.05 (13)	F1—C2'—C3'	117.55 (12)
C3—C2—H2	119.5	F1—C2'—C1'	118.29 (11)
C1—C2—H2	119.5	C3'—C2'—C1'	124.15 (13)
C4—C3—C2	118.99 (13)	C2'—C3'—C4'	118.55 (13)
C4—C3—H3	120.5	C2'—C3'—H3'	120.7
C2—C3—H3	120.5	C4'—C3'—H3'	120.7
C5—C4—C3	121.38 (12)	C5'—C4'—C3'	119.68 (13)
C5—C4—Cl1	119.09 (11)	C5'—C4'—H4'	120.2
C3—C4—Cl1	119.53 (11)	C3'—C4'—H4'	120.2
C4—C5—C6	119.11 (13)	C4'—C5'—C6'	120.35 (13)
C4—C5—H5	120.4	C4'—C5'—H5'	119.8
C6—C5—H5	120.4	C6'—C5'—H5'	119.8
C5—C6—C1	121.24 (13)	C5'—C6'—C1'	121.58 (13)
C5—C6—H6	119.4	C5'—C6'—H6'	119.2
C1—C6—H6	119.4	C1'—C6'—H6'	119.2
C6—C1—C2—C3	1.0 (2)	C2—C1—C1'—C6'	133.14 (14)
C1'—C1—C2—C3	−177.33 (12)	C6'—C1'—C2'—F1	178.39 (12)
C1—C2—C3—C4	−0.9 (2)	C1—C1'—C2'—F1	−0.80 (19)
C2—C3—C4—C5	0.1 (2)	C6'—C1'—C2'—C3'	−0.3 (2)
C2—C3—C4—Cl1	−179.41 (10)	C1—C1'—C2'—C3'	−179.54 (13)
C3—C4—C5—C6	0.5 (2)	F1—C2'—C3'—C4'	−178.49 (13)
Cl1—C4—C5—C6	−179.95 (11)	C1'—C2'—C3'—C4'	0.3 (2)
C4—C5—C6—C1	−0.4 (2)	C2'—C3'—C4'—C5'	−0.1 (2)
C2—C1—C6—C5	−0.3 (2)	C3'—C4'—C5'—C6'	0.1 (2)
C1'—C1—C6—C5	178.00 (13)	C4'—C5'—C6'—C1'	−0.2 (2)
C6—C1—C1'—C2'	134.03 (14)	C2'—C1'—C6'—C5'	0.3 (2)
C2—C1—C1'—C2'	−47.71 (19)	C1—C1'—C6'—C5'	179.52 (13)
C6—C1—C1'—C6'	−45.12 (19)

(3'F-PCB3)

Crystal data

C12H8ClF	F(000) = 424
Mr = 206.63	Dx = 1.432 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3738 reflections
a = 11.3527 (11) Å	θ = 1.0–27.5°
b = 3.9099 (4) Å	µ = 0.36 mm^−1
c = 21.920 (2) Å	T = 190 K
β = 99.966 (5)°	Prism, colorless
V = 958.30 (16) Å^3	0.40 × 0.12 × 0.12 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1679 independent reflections
Radiation source: fine-focus sealed tube	1430 reflections with I > 2u(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 9 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
CCD ϕ and ω scans	h = −13→13
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −3→4
Tmin = 0.868, Tmax = 0.958	l = −25→26
14766 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 0.4269P] where P = (Fo^2 + 2Fc^2)/3
1679 reflections	(Δ/σ)max = 0.002
167 parameters	Δρmax = 0.21 e Å^−3
45 restraints	Δρmin = −0.25 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

The molecule was positionally disordered (180 degree rotation about the C1—C1' bond of the C1' - C6' ring. Two entire molecules (occ. refined to 0.874 (3):0.126 (3)) were used to model the disorder and were restrained to have the same conformation. The Cl atoms were contrained to have the same coordinates and thermal parameters the minor orientation is indicated by * and " suffixes on the atom labels. Partial atoms in close proximity (<0.5 A) were constrained to have the same thermal parameters.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.66327 (5)	−0.32613 (16)	0.85208 (2)	0.0535 (2)	0.874 (3)
C1	0.41986 (18)	−0.0321 (8)	0.67357 (9)	0.0339 (5)	0.874 (3)
C2	0.5279 (3)	−0.1966 (17)	0.67294 (9)	0.0379 (5)	0.874 (3)
H2	0.5510	−0.2480	0.6343	0.045*	0.874 (3)
C3	0.6031 (4)	−0.2878 (17)	0.72722 (9)	0.0391 (5)	0.874 (3)
H3	0.6765	−0.4021	0.7258	0.047*	0.874 (3)
C4	0.5699 (2)	−0.2102 (8)	0.78339 (9)	0.0382 (5)	0.874 (3)
C5	0.4640 (3)	−0.0421 (14)	0.78585 (10)	0.0395 (7)	0.874 (3)
H5	0.4425	0.0134	0.8247	0.047*	0.874 (3)
C6	0.3895 (3)	0.0445 (12)	0.73142 (10)	0.0368 (9)	0.874 (3)
H6	0.3162	0.1584	0.7332	0.044*	0.874 (3)
C1'	0.3393 (2)	0.0674 (9)	0.61549 (11)	0.0349 (5)	0.874 (3)
C2'	0.3863 (2)	0.1691 (13)	0.56345 (13)	0.0417 (5)	0.874 (3)
H2'	0.4702	0.1711	0.5643	0.050*	0.874 (3)
C3'	0.3082 (2)	0.2663 (14)	0.51095 (12)	0.0466 (6)	0.874 (3)
F1	0.35685 (14)	0.3706 (5)	0.46085 (6)	0.0697 (6)	0.874 (3)
C4'	0.1871 (2)	0.2697 (12)	0.50618 (12)	0.0483 (6)	0.874 (3)
H4'	0.1366	0.3406	0.4692	0.058*	0.874 (3)
C5'	0.1403 (2)	0.1653 (8)	0.55760 (12)	0.0485 (6)	0.874 (3)
H5'	0.0562	0.1621	0.5559	0.058*	0.874 (3)
C6'	0.2150 (2)	0.0664 (7)	0.61103 (11)	0.0416 (5)	0.874 (3)
H6'	0.1812	−0.0042	0.6457	0.050*	0.874 (3)
Cl1*	0.66327 (5)	−0.32613 (16)	0.85208 (2)	0.0535 (2)	0.126 (3)
C1*	0.4343 (9)	−0.008 (5)	0.6709 (3)	0.0339 (5)	0.126 (3)
C2*	0.538 (2)	−0.196 (12)	0.67183 (18)	0.0379 (5)	0.126 (3)
H2*	0.5612	−0.2594	0.6337	0.045*	0.126 (3)
C3*	0.609 (2)	−0.295 (11)	0.72697 (13)	0.0391 (5)	0.126 (3)
H3*	0.6798	−0.4237	0.7267	0.047*	0.126 (3)
C4*	0.5752 (8)	−0.202 (4)	0.78233 (17)	0.0382 (5)	0.126 (3)
C5*	0.473 (2)	−0.015 (10)	0.7832 (3)	0.0395 (7)	0.126 (3)
H5*	0.4501	0.0472	0.8215	0.047*	0.126 (3)
C6*	0.403 (2)	0.081 (10)	0.7279 (4)	0.0368 (9)	0.126 (3)
H6*	0.3322	0.2105	0.7286	0.044*	0.126 (3)
C1"	0.3568 (8)	0.093 (6)	0.6119 (4)	0.0349 (5)	0.126 (3)
C2"	0.2326 (8)	0.107 (4)	0.6078 (3)	0.0416 (5)	0.126 (3)
H2"	0.1964	0.0514	0.6425	0.050*	0.126 (3)
C3"	0.1638 (7)	0.203 (4)	0.5524 (4)	0.0485 (6)	0.126 (3)
F1"	0.0421 (7)	0.215 (3)	0.5497 (4)	0.058*	0.126 (3)
C4"	0.2089 (8)	0.286 (8)	0.5007 (5)	0.0483 (6)	0.126 (3)
H4"	0.1580	0.3506	0.4634	0.058*	0.126 (3)
C5"	0.3321 (9)	0.273 (10)	0.5048 (6)	0.0466 (6)	0.126 (3)
H5"	0.3670	0.3296	0.4697	0.056*	0.126 (3)
C6"	0.4043 (8)	0.178 (9)	0.5593 (6)	0.0417 (5)	0.126 (3)
H6"	0.4885	0.1707	0.5611	0.050*	0.126 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0599 (3)	0.0554 (4)	0.0424 (3)	0.0035 (3)	0.0006 (2)	0.0025 (2)
C1	0.0376 (10)	0.0277 (11)	0.0381 (10)	−0.0083 (9)	0.0116 (8)	−0.0013 (8)
C2	0.0409 (12)	0.0374 (11)	0.0380 (10)	−0.0048 (11)	0.0145 (8)	−0.0055 (9)
C3	0.0368 (10)	0.0357 (12)	0.0460 (11)	−0.0002 (9)	0.0099 (8)	−0.0054 (9)
C4	0.0426 (10)	0.0345 (11)	0.0372 (10)	−0.0071 (8)	0.0061 (8)	0.0005 (8)
C5	0.0477 (12)	0.0371 (15)	0.0374 (10)	−0.0061 (12)	0.0174 (8)	−0.0021 (9)
C6	0.0366 (12)	0.0350 (17)	0.0423 (10)	−0.0028 (13)	0.0160 (8)	0.0021 (10)
C1'	0.0407 (11)	0.0273 (11)	0.0380 (10)	−0.0045 (10)	0.0103 (8)	−0.0039 (8)
C2'	0.0440 (11)	0.0429 (13)	0.0398 (11)	−0.0044 (13)	0.0120 (9)	−0.0030 (10)
C3'	0.0619 (15)	0.0463 (13)	0.0339 (12)	−0.0012 (15)	0.0145 (10)	−0.0007 (11)
F1	0.0726 (10)	0.0997 (14)	0.0398 (8)	0.0041 (9)	0.0176 (7)	0.0142 (8)
C4'	0.0532 (13)	0.0480 (14)	0.0416 (12)	0.0044 (13)	0.0023 (10)	−0.0041 (11)
C5'	0.0391 (13)	0.0519 (16)	0.0540 (13)	−0.0003 (11)	0.0066 (10)	−0.0059 (11)
C6'	0.0420 (11)	0.0384 (13)	0.0462 (11)	−0.0066 (10)	0.0128 (9)	−0.0012 (10)
Cl1*	0.0599 (3)	0.0554 (4)	0.0424 (3)	0.0035 (3)	0.0006 (2)	0.0025 (2)
C1*	0.0376 (10)	0.0277 (11)	0.0381 (10)	−0.0083 (9)	0.0116 (8)	−0.0013 (8)
C2*	0.0409 (12)	0.0374 (11)	0.0380 (10)	−0.0048 (11)	0.0145 (8)	−0.0055 (9)
C3*	0.0368 (10)	0.0357 (12)	0.0460 (11)	−0.0002 (9)	0.0099 (8)	−0.0054 (9)
C4*	0.0426 (10)	0.0345 (11)	0.0372 (10)	−0.0071 (8)	0.0061 (8)	0.0005 (8)
C5*	0.0477 (12)	0.0371 (15)	0.0374 (10)	−0.0061 (12)	0.0174 (8)	−0.0021 (9)
C6*	0.0366 (12)	0.0350 (17)	0.0423 (10)	−0.0028 (13)	0.0160 (8)	0.0021 (10)
C1"	0.0407 (11)	0.0273 (11)	0.0380 (10)	−0.0045 (10)	0.0103 (8)	−0.0039 (8)
C2"	0.0420 (11)	0.0384 (13)	0.0462 (11)	−0.0066 (10)	0.0128 (9)	−0.0012 (10)
C3"	0.0391 (13)	0.0519 (16)	0.0540 (13)	−0.0003 (11)	0.0066 (10)	−0.0059 (11)
C4"	0.0532 (13)	0.0480 (14)	0.0416 (12)	0.0044 (13)	0.0023 (10)	−0.0041 (11)
C5"	0.0619 (15)	0.0463 (13)	0.0339 (12)	−0.0012 (15)	0.0145 (10)	−0.0007 (11)
C6"	0.0440 (11)	0.0429 (13)	0.0398 (11)	−0.0044 (13)	0.0120 (9)	−0.0030 (10)

Geometric parameters (Å, º)

Cl1—C4	1.7447 (19)	C1*—C2*	1.387 (3)
C1—C2	1.388 (3)	C1*—C6*	1.403 (3)
C1—C6	1.403 (3)	C1*—C1"	1.485 (3)
C1—C1'	1.485 (3)	C2*—C3*	1.386 (3)
C2—C3	1.385 (3)	C2*—H2*	0.9500
C2—H2	0.9500	C3*—C4*	1.382 (3)
C3—C4	1.382 (3)	C3*—H3*	0.9500
C3—H3	0.9500	C4*—C5*	1.380 (3)
C4—C5	1.380 (3)	C5*—C6*	1.379 (3)
C5—C6	1.380 (3)	C5*—H5*	0.9500
C5—H5	0.9500	C6*—H6*	0.9500
C6—H6	0.9500	C1"—C6"	1.396 (3)
C1'—C6'	1.397 (3)	C1"—C2"	1.398 (3)
C1'—C2'	1.398 (3)	C2"—C3"	1.379 (4)
C2'—C3'	1.379 (3)	C2"—H2"	0.9500
C2'—H2'	0.9500	C3"—C4"	1.361 (4)
C3'—C4'	1.361 (4)	C3"—F1"	1.373 (3)
C3'—F1	1.374 (3)	C4"—C5"	1.388 (4)
C4'—C5'	1.388 (4)	C4"—H4"	0.9500
C4'—H4'	0.9500	C5"—C6"	1.377 (4)
C5'—C6'	1.377 (3)	C5"—H5"	0.9500
C5'—H5'	0.9500	C6"—H6"	0.9500
C6'—H6'	0.9500
C2—C1—C6	117.64 (17)	C1'—C6'—H6'	119.2
C2—C1—C1'	121.83 (16)	C2*—C1*—C6*	117.7 (2)
C6—C1—C1'	120.52 (16)	C2*—C1*—C1"	121.9 (2)
C3—C2—C1	121.67 (17)	C6*—C1*—C1"	120.4 (2)
C3—C2—H2	119.2	C3*—C2*—C1*	121.7 (2)
C1—C2—H2	119.2	C3*—C2*—H2*	119.2
C4—C3—C2	119.08 (18)	C1*—C2*—H2*	119.2
C4—C3—H3	120.5	C4*—C3*—C2*	119.1 (2)
C2—C3—H3	120.5	C4*—C3*—H3*	120.5
C5—C4—C3	120.88 (18)	C2*—C3*—H3*	120.5
C5—C4—Cl1	119.57 (15)	C5*—C4*—C3*	120.9 (2)
C3—C4—Cl1	119.55 (15)	C6*—C5*—C4*	119.4 (2)
C6—C5—C4	119.40 (17)	C6*—C5*—H5*	120.3
C6—C5—H5	120.3	C4*—C5*—H5*	120.3
C4—C5—H5	120.3	C5*—C6*—C1*	121.3 (2)
C5—C6—C1	121.32 (17)	C5*—C6*—H6*	119.4
C5—C6—H6	119.3	C1*—C6*—H6*	119.4
C1—C6—H6	119.3	C6"—C1"—C2"	117.9 (2)
C6'—C1'—C2'	117.85 (18)	C6"—C1"—C1*	121.8 (2)
C6'—C1'—C1	121.60 (19)	C2"—C1"—C1*	120.3 (2)
C2'—C1'—C1	120.55 (18)	C3"—C2"—C1"	118.5 (3)
C3'—C2'—C1'	118.6 (2)	C3"—C2"—H2"	120.7
C3'—C2'—H2'	120.7	C1"—C2"—H2"	120.7
C1'—C2'—H2'	120.7	C4"—C3"—F1"	118.5 (3)
C4'—C3'—F1	118.4 (2)	C4"—C3"—C2"	124.2 (3)
C4'—C3'—C2'	124.2 (2)	F1"—C3"—C2"	117.3 (3)
F1—C3'—C2'	117.4 (2)	C3"—C4"—C5"	117.3 (2)
C3'—C4'—C5'	117.3 (2)	C3"—C4"—H4"	121.4
C3'—C4'—H4'	121.4	C5"—C4"—H4"	121.4
C5'—C4'—H4'	121.4	C6"—C5"—C4"	120.5 (3)
C6'—C5'—C4'	120.5 (2)	C6"—C5"—H5"	119.8
C6'—C5'—H5'	119.8	C4"—C5"—H5"	119.8
C4'—C5'—H5'	119.8	C5"—C6"—C1"	121.6 (3)
C5'—C6'—C1'	121.6 (2)	C5"—C6"—H6"	119.2
C5'—C6'—H6'	119.2	C1"—C6"—H6"	119.2
C6—C1—C2—C3	1.0 (3)	C1—C1'—C6'—C5'	178.7 (2)
C1'—C1—C2—C3	179.7 (2)	C6*—C1*—C2*—C3*	0.0 (6)
C1—C2—C3—C4	−0.5 (4)	C1"—C1*—C2*—C3*	−178.9 (5)
C2—C3—C4—C5	−0.5 (4)	C1*—C2*—C3*—C4*	0.0 (6)
C2—C3—C4—Cl1	179.6 (2)	C2*—C3*—C4*—C5*	0.0 (14)
C3—C4—C5—C6	1.0 (4)	C3*—C4*—C5*—C6*	0.0 (18)
Cl1—C4—C5—C6	−179.0 (2)	C4*—C5*—C6*—C1*	0.0 (18)
C4—C5—C6—C1	−0.6 (4)	C2*—C1*—C6*—C5*	0.0 (14)
C2—C1—C6—C5	−0.4 (4)	C1"—C1*—C6*—C5*	178.9 (10)
C1'—C1—C6—C5	−179.2 (2)	C2*—C1*—C1"—C6"	−35 (2)
C2—C1—C1'—C6'	146.8 (4)	C6*—C1*—C1"—C6"	146 (3)
C6—C1—C1'—C6'	−34.4 (4)	C2*—C1*—C1"—C2"	145 (2)
C2—C1—C1'—C2'	−33.9 (5)	C6*—C1*—C1"—C2"	−34 (2)
C6—C1—C1'—C2'	144.9 (3)	C6"—C1"—C2"—C3"	0.0 (6)
C6'—C1'—C2'—C3'	0.7 (4)	C1*—C1"—C2"—C3"	179.8 (5)
C1—C1'—C2'—C3'	−178.6 (2)	C1"—C2"—C3"—C4"	0.0 (6)
C1'—C2'—C3'—C4'	−0.1 (4)	C1"—C2"—C3"—F1"	−179.9 (6)
C1'—C2'—C3'—F1	178.9 (4)	F1"—C3"—C4"—C5"	179.8 (10)
F1—C3'—C4'—C5'	−179.6 (4)	C2"—C3"—C4"—C5"	−0.1 (13)
C2'—C3'—C4'—C5'	−0.6 (5)	C3"—C4"—C5"—C6"	0.1 (17)
C3'—C4'—C5'—C6'	0.6 (4)	C4"—C5"—C6"—C1"	−0.1 (18)
C4'—C5'—C6'—C1'	0.0 (4)	C2"—C1"—C6"—C5"	0.0 (13)
C2'—C1'—C6'—C5'	−0.7 (3)	C1*—C1"—C6"—C5"	−179.8 (10)

(4'F-PCB3)

Crystal data

C12H8ClF	F(000) = 848
Mr = 206.63	Dx = 1.403 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 8447 reflections
a = 9.550 (1) Å	θ = 1.0–27.5°
b = 13.1441 (13) Å	µ = 0.36 mm^−1
c = 15.6777 (16) Å	T = 190 K
β = 96.323 (5)°	Prism, colorless
V = 1956.0 (3) Å^3	0.39 × 0.24 × 0.14 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	3447 independent reflections
Radiation source: fine-focus sealed tube	2412 reflections with I > 2u(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 9 pixels mm^-1	θmax = 25.0°, θmin = 2.9°
CCD ϕ and ω scans	h = −11→11
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −15→15
Tmin = 0.873, Tmax = 0.952	l = −18→18
32179 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 0.3255P] where P = (Fo^2 + 2Fc^2)/3
3447 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.17 e Å^−3
86 restraints	Δρmin = −0.32 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

The both molecules in the structure are disordered in the same amount. The second orientation (labels with * and ") can be approximated by inversion through the molecular center. The conformation of the second orientation was restrained to be the same as the first orientation. The relative occupancies refined to 0.841 (3):0.159 (3) and were constrained to sum to 1.0. thermal parameters for atoms in close proximity were (e.g. C1 and C1*) were constrained to be the same and Cl1 and F1* were constrained th have the same coordinates as were Cl2 and F2*, F1 and Cl1* and F2 and Cl2*.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.63996 (6)	0.59936 (4)	0.64831 (4)	0.0567 (2)	0.841 (3)
F1	0.59225 (14)	−0.16982 (9)	0.59803 (8)	0.0843 (5)	0.841 (3)
C1	0.6210 (3)	0.25429 (17)	0.62815 (16)	0.0302 (5)	0.841 (3)
C2	0.6207 (4)	0.30324 (18)	0.70725 (16)	0.0353 (5)	0.841 (3)
H2	0.6165	0.2637	0.7576	0.042*	0.841 (3)
C3	0.6265 (4)	0.40839 (18)	0.71372 (17)	0.0396 (6)	0.841 (3)
H3	0.6259	0.4406	0.7679	0.047*	0.841 (3)
C4	0.6331 (5)	0.46547 (18)	0.64080 (17)	0.0369 (5)	0.841 (3)
C5	0.6347 (5)	0.42005 (19)	0.56213 (17)	0.0394 (6)	0.841 (3)
H5	0.6406	0.4604	0.5124	0.047*	0.841 (3)
C6	0.6277 (5)	0.31502 (18)	0.55552 (17)	0.0362 (5)	0.841 (3)
H6	0.6276	0.2838	0.5008	0.043*	0.841 (3)
C1'	0.6137 (3)	0.14217 (18)	0.62077 (18)	0.0318 (5)	0.841 (3)
C2'	0.5282 (3)	0.08524 (18)	0.6694 (2)	0.0382 (6)	0.841 (3)
H2'	0.4754	0.1189	0.7089	0.046*	0.841 (3)
C3'	0.5190 (4)	−0.0194 (2)	0.6610 (2)	0.0475 (6)	0.841 (3)
H3'	0.4595	−0.0575	0.6937	0.057*	0.841 (3)
C4'	0.5972 (5)	−0.0667 (2)	0.6048 (3)	0.0501 (6)	0.841 (3)
C5'	0.6848 (5)	−0.0140 (2)	0.5563 (3)	0.0517 (7)	0.841 (3)
H5'	0.7398	−0.0489	0.5186	0.062*	0.841 (3)
C6'	0.6907 (4)	0.09043 (19)	0.5637 (2)	0.0407 (6)	0.841 (3)
H6'	0.7483	0.1279	0.5293	0.049*	0.841 (3)
Cl1*	0.59225 (14)	−0.16982 (9)	0.59803 (8)	0.0843 (5)	0.159 (3)
F1*	0.63996 (6)	0.59936 (4)	0.64831 (4)	0.0567 (2)	0.159 (3)
C1*	0.6176 (17)	0.1741 (4)	0.6245 (10)	0.0318 (5)	0.159 (3)
C2*	0.5358 (19)	0.1160 (5)	0.6749 (10)	0.0382 (6)	0.159 (3)
H2*	0.4844	0.1492	0.7154	0.046*	0.159 (3)
C3*	0.528 (2)	0.0114 (5)	0.6670 (11)	0.0475 (6)	0.159 (3)
H3*	0.4712	−0.0269	0.7015	0.057*	0.159 (3)
C4*	0.603 (3)	−0.0367 (4)	0.6088 (15)	0.0501 (6)	0.159 (3)
C5*	0.682 (3)	0.0179 (5)	0.5569 (17)	0.0517 (7)	0.159 (3)
H5*	0.7312	−0.0161	0.5157	0.062*	0.159 (3)
C6*	0.690 (3)	0.1226 (5)	0.5648 (14)	0.0407 (6)	0.159 (3)
H6*	0.7457	0.1601	0.5292	0.049*	0.159 (3)
C1'*	0.6235 (19)	0.2861 (4)	0.6312 (7)	0.0302 (5)	0.159 (3)
C2'*	0.626 (2)	0.3350 (5)	0.7104 (6)	0.0353 (5)	0.159 (3)
H2'*	0.6242	0.2956	0.7610	0.042*	0.159 (3)
C3'*	0.632 (2)	0.4398 (4)	0.7165 (5)	0.0396 (6)	0.159 (3)
H3'*	0.6331	0.4724	0.7706	0.047*	0.159 (3)
C4'*	0.637 (3)	0.4958 (4)	0.6435 (5)	0.0369 (5)	0.159 (3)
C5'*	0.630 (3)	0.4512 (5)	0.5636 (5)	0.0394 (6)	0.159 (3)
H5'*	0.6271	0.4917	0.5132	0.047*	0.159 (3)
C6'*	0.628 (3)	0.3466 (5)	0.5584 (6)	0.0362 (5)	0.159 (3)
H6'*	0.6300	0.3149	0.5041	0.043*	0.159 (3)
Cl2	0.13834 (8)	0.85674 (5)	0.63520 (4)	0.0680 (3)	0.841 (3)
F2	0.10814 (12)	0.08459 (8)	0.61270 (8)	0.0698 (5)	0.841 (3)
C1A	0.1283 (3)	0.51280 (19)	0.6285 (2)	0.0328 (5)	0.841 (3)
C2A	0.2492 (3)	0.5654 (2)	0.6627 (3)	0.0395 (6)	0.841 (3)
H2A	0.3303	0.5281	0.6849	0.047*	0.841 (3)
C3A	0.2527 (3)	0.6701 (2)	0.6649 (3)	0.0442 (6)	0.841 (3)
H3A	0.3353	0.7048	0.6884	0.053*	0.841 (3)
C4A	0.1340 (3)	0.7241 (2)	0.6323 (3)	0.0430 (6)	0.841 (3)
C5A	0.0135 (3)	0.6750 (2)	0.5984 (3)	0.0415 (7)	0.841 (3)
H5A	−0.0673	0.7128	0.5765	0.050*	0.841 (3)
C6A	0.0113 (3)	0.5698 (2)	0.5966 (3)	0.0374 (6)	0.841 (3)
H6A	−0.0719	0.5358	0.5732	0.045*	0.841 (3)
C1'A	0.1247 (3)	0.40065 (19)	0.6249 (2)	0.0330 (5)	0.841 (3)
C2'A	0.2402 (3)	0.3450 (2)	0.6031 (3)	0.0378 (6)	0.841 (3)
H2'A	0.3232	0.3800	0.5918	0.045*	0.841 (3)
C3'A	0.2362 (3)	0.2401 (2)	0.5977 (3)	0.0427 (6)	0.841 (3)
H3'A	0.3146	0.2031	0.5816	0.051*	0.841 (3)
C4'A	0.1169 (3)	0.19045 (19)	0.6161 (4)	0.0429 (6)	0.841 (3)
C5'A	0.0018 (3)	0.2413 (2)	0.6401 (3)	0.0438 (7)	0.841 (3)
H5'A	−0.0785	0.2051	0.6543	0.053*	0.841 (3)
C6'A	0.0054 (3)	0.34586 (19)	0.6430 (3)	0.0372 (6)	0.841 (3)
H6'A	−0.0749	0.3819	0.6576	0.045*	0.841 (3)
Cl2*	0.10814 (12)	0.08459 (8)	0.61270 (8)	0.0698 (5)	0.159 (3)
F2*	0.13834 (8)	0.85674 (5)	0.63520 (4)	0.0680 (3)	0.159 (3)
C1A*	0.1290 (16)	0.4281 (4)	0.6273 (14)	0.0330 (5)	0.159 (3)
C2A*	0.2449 (16)	0.3702 (6)	0.6082 (18)	0.0378 (6)	0.159 (3)
H2A*	0.3298	0.4038	0.5985	0.045*	0.159 (3)
C3A*	0.2382 (14)	0.2659 (5)	0.6032 (19)	0.0427 (6)	0.159 (3)
H3A*	0.3172	0.2278	0.5894	0.051*	0.159 (3)
C4A*	0.1146 (15)	0.2169 (4)	0.618 (2)	0.0429 (6)	0.159 (3)
C5A*	−0.0032 (14)	0.2714 (5)	0.633 (2)	0.0438 (7)	0.159 (3)
H5A*	−0.0897	0.2375	0.6383	0.053*	0.159 (3)
C6A*	0.0056 (16)	0.3763 (5)	0.639 (2)	0.0372 (6)	0.159 (3)
H6A*	−0.0744	0.4138	0.6523	0.045*	0.159 (3)
C1A"	0.1342 (16)	0.5402 (4)	0.6285 (13)	0.0328 (5)	0.159 (3)
C2A"	0.2542 (15)	0.5924 (5)	0.6637 (15)	0.0395 (6)	0.159 (3)
H2A"	0.3343	0.5548	0.6872	0.047*	0.159 (3)
C3A"	0.2592 (13)	0.6974 (5)	0.6652 (16)	0.0442 (6)	0.159 (3)
H3A"	0.3410	0.7320	0.6902	0.053*	0.159 (3)
C4A"	0.1439 (14)	0.7510 (4)	0.6299 (18)	0.0430 (6)	0.159 (3)
C5A"	0.0246 (16)	0.7032 (5)	0.5923 (17)	0.0415 (7)	0.159 (3)
H5A"	−0.0526	0.7417	0.5660	0.050*	0.159 (3)
C6A"	0.0192 (18)	0.5989 (6)	0.594 (2)	0.0374 (6)	0.159 (3)
H6A"	−0.0647	0.5656	0.5702	0.045*	0.159 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0460 (4)	0.0385 (4)	0.0862 (5)	−0.0013 (3)	0.0096 (3)	−0.0024 (3)
F1	0.1177 (11)	0.0473 (8)	0.0849 (10)	−0.0040 (7)	−0.0028 (8)	−0.0082 (6)
C1	0.0285 (10)	0.0270 (14)	0.0357 (11)	0.0001 (13)	0.0059 (8)	0.0017 (10)
C2	0.0381 (11)	0.0370 (15)	0.0316 (11)	−0.0004 (15)	0.0076 (9)	0.0009 (11)
C3	0.0387 (12)	0.0340 (16)	0.0464 (13)	0.0001 (15)	0.0067 (9)	−0.0093 (11)
C4	0.0261 (11)	0.0277 (14)	0.0573 (14)	−0.0016 (18)	0.0060 (9)	−0.0001 (11)
C5	0.0348 (12)	0.0358 (16)	0.0478 (13)	0.000 (2)	0.0057 (9)	0.0101 (11)
C6	0.0361 (11)	0.0377 (15)	0.0357 (11)	0.000 (2)	0.0078 (9)	−0.0009 (12)
C1'	0.0327 (11)	0.0339 (14)	0.0281 (10)	−0.0006 (13)	0.0006 (8)	−0.0021 (12)
C2'	0.0454 (12)	0.0328 (16)	0.0367 (12)	−0.0006 (13)	0.0064 (10)	0.0034 (12)
C3'	0.0591 (15)	0.0412 (17)	0.0411 (13)	−0.0074 (15)	0.0013 (11)	0.0065 (14)
C4'	0.0698 (16)	0.0254 (15)	0.0510 (14)	−0.0024 (18)	−0.0117 (13)	−0.0033 (16)
C5'	0.0583 (14)	0.0473 (17)	0.0489 (13)	0.009 (2)	0.0035 (11)	−0.0147 (19)
C6'	0.0464 (12)	0.0358 (17)	0.0405 (12)	−0.0026 (18)	0.0077 (10)	−0.0071 (17)
Cl1*	0.1177 (11)	0.0473 (8)	0.0849 (10)	−0.0040 (7)	−0.0028 (8)	−0.0082 (6)
F1*	0.0460 (4)	0.0385 (4)	0.0862 (5)	−0.0013 (3)	0.0096 (3)	−0.0024 (3)
C1*	0.0327 (11)	0.0339 (14)	0.0281 (10)	−0.0006 (13)	0.0006 (8)	−0.0021 (12)
C2*	0.0454 (12)	0.0328 (16)	0.0367 (12)	−0.0006 (13)	0.0064 (10)	0.0034 (12)
C3*	0.0591 (15)	0.0412 (17)	0.0411 (13)	−0.0074 (15)	0.0013 (11)	0.0065 (14)
C4*	0.0698 (16)	0.0254 (15)	0.0510 (14)	−0.0024 (18)	−0.0117 (13)	−0.0033 (16)
C5*	0.0583 (14)	0.0473 (17)	0.0489 (13)	0.009 (2)	0.0035 (11)	−0.0147 (19)
C6*	0.0464 (12)	0.0358 (17)	0.0405 (12)	−0.0026 (18)	0.0077 (10)	−0.0071 (17)
C1'*	0.0285 (10)	0.0270 (14)	0.0357 (11)	0.0001 (13)	0.0059 (8)	0.0017 (10)
C2'*	0.0381 (11)	0.0370 (15)	0.0316 (11)	−0.0004 (15)	0.0076 (9)	0.0009 (11)
C3'*	0.0387 (12)	0.0340 (16)	0.0464 (13)	0.0001 (15)	0.0067 (9)	−0.0093 (11)
C4'*	0.0261 (11)	0.0277 (14)	0.0573 (14)	−0.0016 (18)	0.0060 (9)	−0.0001 (11)
C5'*	0.0348 (12)	0.0358 (16)	0.0478 (13)	0.000 (2)	0.0057 (9)	0.0101 (11)
C6'*	0.0361 (11)	0.0377 (15)	0.0357 (11)	0.000 (2)	0.0078 (9)	−0.0009 (12)
Cl2	0.0943 (6)	0.0461 (4)	0.0695 (5)	−0.0107 (3)	0.0354 (4)	−0.0014 (3)
F2	0.0776 (8)	0.0488 (8)	0.0835 (9)	0.0083 (6)	0.0111 (6)	−0.0036 (6)
C1A	0.0337 (11)	0.0373 (14)	0.0284 (10)	0.0005 (11)	0.0076 (8)	−0.0046 (13)
C2A	0.0347 (11)	0.0451 (15)	0.0395 (11)	−0.0017 (12)	0.0076 (9)	−0.0044 (16)
C3A	0.0482 (13)	0.0437 (17)	0.0424 (12)	−0.0100 (12)	0.0129 (10)	−0.0055 (16)
C4A	0.0636 (15)	0.0330 (14)	0.0361 (12)	−0.0050 (13)	0.0224 (12)	−0.0005 (17)
C5A	0.0520 (14)	0.0404 (17)	0.0328 (13)	0.0044 (13)	0.0080 (11)	0.0029 (16)
C6A	0.0390 (12)	0.0393 (15)	0.0336 (12)	0.0016 (13)	0.0025 (10)	−0.0042 (19)
C1'A	0.0321 (11)	0.0380 (14)	0.0282 (10)	0.0007 (12)	0.0003 (8)	−0.0054 (14)
C2'A	0.0301 (11)	0.0429 (16)	0.0409 (13)	0.0014 (11)	0.0059 (9)	−0.0043 (15)
C3'A	0.0379 (12)	0.0430 (16)	0.0469 (14)	0.0070 (12)	0.0030 (10)	−0.0037 (18)
C4'A	0.0497 (13)	0.0314 (15)	0.0465 (13)	0.0025 (13)	0.0007 (10)	−0.004 (2)
C5'A	0.0395 (12)	0.0436 (16)	0.0482 (17)	−0.0081 (13)	0.0041 (11)	0.003 (2)
C6'A	0.0290 (11)	0.0405 (17)	0.0422 (13)	0.0011 (12)	0.0046 (9)	−0.004 (2)
Cl2*	0.0776 (8)	0.0488 (8)	0.0835 (9)	0.0083 (6)	0.0111 (6)	−0.0036 (6)
F2*	0.0943 (6)	0.0461 (4)	0.0695 (5)	−0.0107 (3)	0.0354 (4)	−0.0014 (3)
C1A*	0.0321 (11)	0.0380 (14)	0.0282 (10)	0.0007 (12)	0.0003 (8)	−0.0054 (14)
C2A*	0.0301 (11)	0.0429 (16)	0.0409 (13)	0.0014 (11)	0.0059 (9)	−0.0043 (15)
C3A*	0.0379 (12)	0.0430 (16)	0.0469 (14)	0.0070 (12)	0.0030 (10)	−0.0037 (18)
C4A*	0.0497 (13)	0.0314 (15)	0.0465 (13)	0.0025 (13)	0.0007 (10)	−0.004 (2)
C5A*	0.0395 (12)	0.0436 (16)	0.0482 (17)	−0.0081 (13)	0.0041 (11)	0.003 (2)
C6A*	0.0290 (11)	0.0405 (17)	0.0422 (13)	0.0011 (12)	0.0046 (9)	−0.004 (2)
C1A"	0.0337 (11)	0.0373 (14)	0.0284 (10)	0.0005 (11)	0.0076 (8)	−0.0046 (13)
C2A"	0.0347 (11)	0.0451 (15)	0.0395 (11)	−0.0017 (12)	0.0076 (9)	−0.0044 (16)
C3A"	0.0482 (13)	0.0437 (17)	0.0424 (12)	−0.0100 (12)	0.0129 (10)	−0.0055 (16)
C4A"	0.0636 (15)	0.0330 (14)	0.0361 (12)	−0.0050 (13)	0.0224 (12)	−0.0005 (17)
C5A"	0.0520 (14)	0.0404 (17)	0.0328 (13)	0.0044 (13)	0.0080 (11)	0.0029 (16)
C6A"	0.0390 (12)	0.0393 (15)	0.0336 (12)	0.0016 (13)	0.0025 (10)	−0.0042 (19)

Geometric parameters (Å, º)

Cl1—C4	1.765 (2)	Cl2—C4A	1.744 (3)
F1—C4'	1.360 (3)	F2—C4'A	1.395 (3)
C1—C2	1.397 (3)	C1A—C6A	1.392 (3)
C1—C6	1.398 (3)	C1A—C2A	1.401 (3)
C1—C1'	1.479 (3)	C1A—C1'A	1.475 (3)
C2—C3	1.387 (3)	C2A—C3A	1.377 (3)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C4	1.375 (3)	C3A—C4A	1.386 (4)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.372 (3)	C4A—C5A	1.374 (3)
C5—C6	1.385 (3)	C5A—C6A	1.383 (3)
C5—H5	0.9500	C5A—H5A	0.9500
C6—H6	0.9500	C6A—H6A	0.9500
C1'—C2'	1.394 (3)	C1'A—C2'A	1.397 (3)
C1'—C6'	1.395 (3)	C1'A—C6'A	1.403 (3)
C2'—C3'	1.383 (3)	C2'A—C3'A	1.381 (3)
C2'—H2'	0.9500	C2'A—H2'A	0.9500
C3'—C4'	1.366 (4)	C3'A—C4'A	1.371 (3)
C3'—H3'	0.9500	C3'A—H3'A	0.9500
C4'—C5'	1.378 (4)	C4'A—C5'A	1.374 (3)
C5'—C6'	1.379 (3)	C5'A—C6'A	1.375 (3)
C5'—H5'	0.9500	C5'A—H5'A	0.9500
C6'—H6'	0.9500	C6'A—H6'A	0.9500
C1*—C6*	1.398 (5)	C1A*—C6A*	1.392 (5)
C1*—C2*	1.398 (5)	C1A*—C2A*	1.402 (5)
C1*—C1'*	1.476 (4)	C1A*—C1A"	1.474 (4)
C2*—C3*	1.382 (5)	C2A*—C3A*	1.374 (5)
C2*—H2*	0.9500	C2A*—H2A*	0.9500
C3*—C4*	1.376 (5)	C3A*—C4A*	1.388 (6)
C3*—H3*	0.9500	C3A*—H3A*	0.9500
C4*—C5*	1.372 (5)	C4A*—C5A*	1.374 (5)
C5*—C6*	1.383 (5)	C5A*—C6A*	1.384 (5)
C5*—H5*	0.9500	C5A*—H5A*	0.9500
C6*—H6*	0.9500	C6A*—H6A*	0.9500
C1'*—C2'*	1.395 (5)	C1A"—C2A"	1.397 (5)
C1'*—C6'*	1.396 (5)	C1A"—C6A"	1.403 (5)
C2'*—C3'*	1.382 (5)	C2A"—C3A"	1.381 (5)
C2'*—H2'*	0.9500	C2A"—H2A"	0.9500
C3'*—C4'*	1.365 (6)	C3A"—C4A"	1.371 (5)
C3'*—H3'*	0.9500	C3A"—H3A"	0.9500
C4'*—C5'*	1.378 (6)	C4A"—C5A"	1.375 (5)
C5'*—C6'*	1.377 (5)	C5A"—C6A"	1.372 (5)
C5'*—H5'*	0.9500	C5A"—H5A"	0.9500
C6'*—H6'*	0.9500	C6A"—H6A"	0.9500
C2—C1—C6	117.7 (2)	C6A—C1A—C2A	117.8 (2)
C2—C1—C1'	121.6 (2)	C6A—C1A—C1'A	120.7 (2)
C6—C1—C1'	120.7 (2)	C2A—C1A—C1'A	121.5 (2)
C3—C2—C1	121.3 (2)	C3A—C2A—C1A	121.3 (2)
C3—C2—H2	119.3	C3A—C2A—H2A	119.4
C1—C2—H2	119.3	C1A—C2A—H2A	119.4
C4—C3—C2	119.2 (2)	C2A—C3A—C4A	119.1 (2)
C4—C3—H3	120.4	C2A—C3A—H3A	120.4
C2—C3—H3	120.4	C4A—C3A—H3A	120.4
C5—C4—C3	121.1 (2)	C5A—C4A—C3A	121.2 (2)
C5—C4—Cl1	119.34 (19)	C5A—C4A—Cl2	119.7 (2)
C3—C4—Cl1	119.57 (18)	C3A—C4A—Cl2	119.1 (2)
C4—C5—C6	119.7 (2)	C4A—C5A—C6A	119.2 (2)
C4—C5—H5	120.1	C4A—C5A—H5A	120.4
C6—C5—H5	120.1	C6A—C5A—H5A	120.4
C5—C6—C1	120.9 (2)	C5A—C6A—C1A	121.4 (2)
C5—C6—H6	119.5	C5A—C6A—H6A	119.3
C1—C6—H6	119.5	C1A—C6A—H6A	119.3
C2'—C1'—C6'	118.0 (2)	C2'A—C1'A—C6'A	117.5 (2)
C2'—C1'—C1	121.1 (2)	C2'A—C1'A—C1A	121.2 (2)
C6'—C1'—C1	120.8 (2)	C6'A—C1'A—C1A	121.4 (2)
C3'—C2'—C1'	121.1 (2)	C3'A—C2'A—C1'A	121.4 (2)
C3'—C2'—H2'	119.4	C3'A—C2'A—H2'A	119.3
C1'—C2'—H2'	119.4	C1'A—C2'A—H2'A	119.3
C4'—C3'—C2'	118.7 (2)	C4'A—C3'A—C2'A	118.7 (2)
C4'—C3'—H3'	120.7	C4'A—C3'A—H3'A	120.7
C2'—C3'—H3'	120.7	C2'A—C3'A—H3'A	120.7
F1—C4'—C3'	119.2 (2)	C3'A—C4'A—C5'A	122.3 (2)
F1—C4'—C5'	118.4 (2)	C3'A—C4'A—F2	121.0 (2)
C3'—C4'—C5'	122.4 (2)	C5'A—C4'A—F2	116.7 (2)
C4'—C5'—C6'	118.4 (2)	C4'A—C5'A—C6'A	118.5 (2)
C4'—C5'—H5'	120.8	C4'A—C5'A—H5'A	120.7
C6'—C5'—H5'	120.8	C6'A—C5'A—H5'A	120.7
C5'—C6'—C1'	121.4 (2)	C5'A—C6'A—C1'A	121.6 (2)
C5'—C6'—H6'	119.3	C5'A—C6'A—H6'A	119.2
C1'—C6'—H6'	119.3	C1'A—C6'A—H6'A	119.2
C6*—C1*—C2*	117.5 (3)	C6A*—C1A*—C2A*	117.6 (4)
C6*—C1*—C1'*	120.9 (5)	C6A*—C1A*—C1A"	121.0 (5)
C2*—C1*—C1'*	121.6 (5)	C2A*—C1A*—C1A"	121.3 (5)
C3*—C2*—C1*	121.4 (4)	C3A*—C2A*—C1A*	121.4 (4)
C3*—C2*—H2*	119.3	C3A*—C2A*—H2A*	119.3
C1*—C2*—H2*	119.3	C1A*—C2A*—H2A*	119.3
C4*—C3*—C2*	119.3 (4)	C2A*—C3A*—C4A*	119.2 (4)
C4*—C3*—H3*	120.3	C2A*—C3A*—H3A*	120.4
C2*—C3*—H3*	120.3	C4A*—C3A*—H3A*	120.4
C5*—C4*—C3*	121.0 (4)	C5A*—C4A*—C3A*	121.0 (4)
C4*—C5*—C6*	119.7 (4)	C4A*—C5A*—C6A*	119.1 (5)
C4*—C5*—H5*	120.2	C4A*—C5A*—H5A*	120.4
C6*—C5*—H5*	120.2	C6A*—C5A*—H5A*	120.4
C5*—C6*—C1*	121.1 (4)	C5A*—C6A*—C1A*	121.5 (4)
C5*—C6*—H6*	119.5	C5A*—C6A*—H6A*	119.2
C1*—C6*—H6*	119.5	C1A*—C6A*—H6A*	119.2
C2'*—C1'*—C6'*	117.7 (4)	C2A"—C1A"—C6A"	117.2 (4)
C2'*—C1'*—C1*	121.3 (5)	C2A"—C1A"—C1A*	121.4 (5)
C6'*—C1'*—C1*	120.9 (5)	C6A"—C1A"—C1A*	121.4 (5)
C3'*—C2'*—C1'*	121.2 (4)	C3A"—C2A"—C1A"	121.5 (4)
C3'*—C2'*—H2'*	119.4	C3A"—C2A"—H2A"	119.2
C1'*—C2'*—H2'*	119.4	C1A"—C2A"—H2A"	119.2
C4'*—C3'*—C2'*	118.9 (4)	C4A"—C3A"—C2A"	118.8 (4)
C4'*—C3'*—H3'*	120.5	C4A"—C3A"—H3A"	120.6
C2'*—C3'*—H3'*	120.5	C2A"—C3A"—H3A"	120.6
C3'*—C4'*—C5'*	122.1 (4)	C3A"—C4A"—C5A"	122.0 (4)
C6'*—C5'*—C4'*	118.5 (4)	C6A"—C5A"—C4A"	118.7 (4)
C6'*—C5'*—H5'*	120.8	C6A"—C5A"—H5A"	120.6
C4'*—C5'*—H5'*	120.8	C4A"—C5A"—H5A"	120.6
C5'*—C6'*—C1'*	121.5 (4)	C5A"—C6A"—C1A"	121.7 (4)
C5'*—C6'*—H6'*	119.3	C5A"—C6A"—H6A"	119.1
C1'*—C6'*—H6'*	119.3	C1A"—C6A"—H6A"	119.1
C6—C1—C2—C3	0.2 (4)	C6A—C1A—C2A—C3A	−0.1 (4)
C1'—C1—C2—C3	−179.5 (3)	C1'A—C1A—C2A—C3A	179.1 (3)
C1—C2—C3—C4	−0.3 (4)	C1A—C2A—C3A—C4A	−0.1 (4)
C2—C3—C4—C5	−0.3 (6)	C2A—C3A—C4A—C5A	0.3 (6)
C2—C3—C4—Cl1	179.8 (3)	C2A—C3A—C4A—Cl2	179.9 (3)
C3—C4—C5—C6	0.8 (7)	C3A—C4A—C5A—C6A	−0.3 (7)
Cl1—C4—C5—C6	−179.3 (4)	Cl2—C4A—C5A—C6A	−179.9 (4)
C4—C5—C6—C1	−0.8 (7)	C4A—C5A—C6A—C1A	0.1 (7)
C2—C1—C6—C5	0.3 (6)	C2A—C1A—C6A—C5A	0.1 (6)
C1'—C1—C6—C5	−179.9 (4)	C1'A—C1A—C6A—C5A	−179.1 (4)
C2—C1—C1'—C2'	39.0 (4)	C6A—C1A—C1'A—C2'A	139.0 (4)
C6—C1—C1'—C2'	−140.7 (4)	C2A—C1A—C1'A—C2'A	−40.2 (4)
C2—C1—C1'—C6'	−142.1 (4)	C6A—C1A—C1'A—C6'A	−40.9 (5)
C6—C1—C1'—C6'	38.1 (5)	C2A—C1A—C1'A—C6'A	139.9 (4)
C6'—C1'—C2'—C3'	−0.4 (4)	C6'A—C1'A—C2'A—C3'A	1.4 (4)
C1—C1'—C2'—C3'	178.5 (3)	C1A—C1'A—C2'A—C3'A	−178.5 (3)
C1'—C2'—C3'—C4'	0.9 (4)	C1'A—C2'A—C3'A—C4'A	−1.5 (5)
C2'—C3'—C4'—F1	178.0 (3)	C2'A—C3'A—C4'A—C5'A	−0.3 (7)
C2'—C3'—C4'—C5'	0.0 (6)	C2'A—C3'A—C4'A—F2	−179.2 (4)
F1—C4'—C5'—C6'	−179.5 (5)	C3'A—C4'A—C5'A—C6'A	2.1 (8)
C3'—C4'—C5'—C6'	−1.5 (8)	F2—C4'A—C5'A—C6'A	−179.0 (5)
C4'—C5'—C6'—C1'	2.0 (8)	C4'A—C5'A—C6'A—C1'A	−2.1 (8)
C2'—C1'—C6'—C5'	−1.1 (6)	C2'A—C1'A—C6'A—C5'A	0.4 (6)
C1—C1'—C6'—C5'	180.0 (4)	C1A—C1'A—C6'A—C5'A	−179.7 (4)
C6*—C1*—C2*—C3*	0.8 (19)	C6A*—C1A*—C2A*—C3A*	−1 (2)
C1'*—C1*—C2*—C3*	178.4 (13)	C1A"—C1A*—C2A*—C3A*	−177.0 (14)
C1*—C2*—C3*—C4*	0.5 (18)	C1A*—C2A*—C3A*—C4A*	−0.8 (19)
C2*—C3*—C4*—C5*	−2 (4)	C2A*—C3A*—C4A*—C5A*	4 (4)
C3*—C4*—C5*—C6*	2 (5)	C3A*—C4A*—C5A*—C6A*	−5 (5)
C4*—C5*—C6*—C1*	−1 (5)	C4A*—C5A*—C6A*—C1A*	3 (5)
C2*—C1*—C6*—C5*	−1 (4)	C2A*—C1A*—C6A*—C5A*	0 (4)
C1'*—C1*—C6*—C5*	−178 (3)	C1A"—C1A*—C6A*—C5A*	176 (3)
C6*—C1*—C1'*—C2'*	−143 (2)	C6A*—C1A*—C1A"—C2A"	144 (2)
C2*—C1*—C1'*—C2'*	39.0 (19)	C2A*—C1A*—C1A"—C2A"	−41 (2)
C6*—C1*—C1'*—C6'*	36 (3)	C6A*—C1A*—C1A"—C6A"	−37 (3)
C2*—C1*—C1'*—C6'*	−142 (2)	C2A*—C1A*—C1A"—C6A"	139 (2)
C6'*—C1'*—C2'*—C3'*	0.6 (19)	C6A"—C1A"—C2A"—C3A"	1 (2)
C1*—C1'*—C2'*—C3'*	179.8 (13)	C1A*—C1A"—C2A"—C3A"	−179.8 (14)
C1'*—C2'*—C3'*—C4'*	−0.7 (17)	C1A"—C2A"—C3A"—C4A"	−1.0 (18)
C2'*—C3'*—C4'*—C5'*	3 (3)	C2A"—C3A"—C4A"—C5A"	−1 (4)
C3'*—C4'*—C5'*—C6'*	−4 (5)	C3A"—C4A"—C5A"—C6A"	3 (5)
C4'*—C5'*—C6'*—C1'*	4 (5)	C4A"—C5A"—C6A"—C1A"	−3 (5)
C2'*—C1'*—C6'*—C5'*	−2 (4)	C2A"—C1A"—C6A"—C5A"	1 (4)
C1*—C1'*—C6'*—C5'*	178 (3)	C1A*—C1A"—C6A"—C5A"	−178 (3)