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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106054255/bk5043sup1.cif
Contains datablocks 3F-PCB3, 2F-PCB3, 2'F-PCB3, 3'F-PCB3, 4'F-PCB3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106054255/bk50432F-PCB3sup2.hkl
Contains datablock 2F-PCB3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106054255/bk50433F-PCB3sup3.hkl
Contains datablock 3F-PCB3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106054255/bk50432primeF-PCB3sup4.hkl
Contains datablock 2'F-PCB3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106054255/bk50433primeF-PCB3sup5.hkl
Contains datablock 3'F-PCB3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106054255/bk50434primeF-PCB3sup6.hkl
Contains datablock 4'F-PCB3

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768106054255/bk5043sup7.pdf
CSD search results

CCDC references: 644714; 644715; 644716; 644717; 644718

Computing details top

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 top
[Figure 1]
[Figure 2]
(3F-PCB3) top
Crystal data top
C12H8ClFF(000) = 848
Mr = 206.63Dx = 1.432 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8130 reflections
a = 11.9836 (7) Åθ = 1.0–27.5°
b = 7.3820 (12) ŵ = 0.36 mm1
c = 21.670 (2) ÅT = 190 K
V = 1917.0 (4) Å3Needle, colorless
Z = 80.35 × 0.08 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
1691 independent reflections
Radiation source: fine-focus sealed tube1367 reflections with I > 2u(I)
Graphite monochromatorRint = 0.050
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 3.4°
CCD ϕ and ω scansh = 1414
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
k = 88
Tmin = 0.883, Tmax = 0.975l = 2525
34729 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0686P)2 + 2.4606P]
where P = (Fo2 + 2Fc2)/3
1691 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C12H8ClFV = 1917.0 (4) Å3
Mr = 206.63Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.9836 (7) ŵ = 0.36 mm1
b = 7.3820 (12) ÅT = 190 K
c = 21.670 (2) Å0.35 × 0.08 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
1691 independent reflections
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
1367 reflections with I > 2u(I)
Tmin = 0.883, Tmax = 0.975Rint = 0.050
34729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.06Δρmax = 0.31 e Å3
1691 reflectionsΔρmin = 0.30 e Å3
127 parameters
Special details top

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

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 (Å2) top
xyzUiso*/Ueq
Cl10.17083 (7)0.54259 (12)0.56951 (3)0.0495 (3)
F10.40076 (16)0.5729 (3)0.53112 (8)0.0579 (6)
C10.2982 (2)0.7029 (3)0.38027 (12)0.0268 (6)
C20.3717 (2)0.6615 (4)0.42809 (12)0.0320 (6)
H20.44990.66550.42130.038*
C30.3306 (2)0.6151 (4)0.48510 (12)0.0342 (7)
C40.2180 (3)0.6069 (4)0.49715 (12)0.0339 (7)
C50.1442 (3)0.6499 (4)0.45078 (14)0.0366 (7)
H50.06620.64690.45840.044*
C60.1836 (2)0.6975 (4)0.39297 (12)0.0302 (6)
H60.13200.72710.36130.036*
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)
H2'0.48550.86760.34260.038*
C3'0.4761 (3)0.8832 (4)0.24931 (15)0.0381 (7)
H3'0.54550.94310.24380.046*
C4'0.4106 (3)0.8412 (4)0.19855 (14)0.0395 (7)
H4'0.43460.87380.15830.047*
C5'0.3103 (2)0.7518 (4)0.20684 (13)0.0362 (7)
H5'0.26570.72190.17210.043*
C6'0.2746 (2)0.7056 (4)0.26532 (12)0.0306 (6)
H6'0.20580.64350.27040.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0624 (6)0.0567 (6)0.0293 (4)0.0053 (4)0.0090 (3)0.0020 (3)
F10.0512 (12)0.0833 (15)0.0393 (10)0.0104 (10)0.0075 (9)0.0098 (10)
C10.0313 (14)0.0202 (13)0.0288 (14)0.0002 (11)0.0024 (11)0.0027 (11)
C20.0309 (14)0.0316 (15)0.0334 (15)0.0010 (12)0.0014 (12)0.0008 (12)
C30.0431 (17)0.0336 (16)0.0261 (14)0.0041 (12)0.0086 (12)0.0000 (12)
C40.0459 (18)0.0289 (15)0.0268 (14)0.0034 (13)0.0052 (13)0.0026 (11)
C50.0385 (16)0.0357 (16)0.0355 (15)0.0013 (13)0.0026 (13)0.0037 (13)
C60.0299 (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) top
Cl1—C41.733 (3)C1'—C2'1.392 (4)
F1—C31.341 (3)C1'—C6'1.404 (4)
C1—C21.394 (4)C2'—C3'1.386 (4)
C1—C61.400 (4)C2'—H2'0.9500
C1—C1'1.488 (4)C3'—C4'1.386 (4)
C2—C31.373 (4)C3'—H3'0.9500
C2—H20.9500C4'—C5'1.383 (4)
C3—C41.377 (4)C4'—H4'0.9500
C4—C51.375 (4)C5'—C6'1.380 (4)
C5—C61.384 (4)C5'—H5'0.9500
C5—H50.9500C6'—H6'0.9500
C6—H60.9500
C2—C1—C6117.8 (2)C2'—C1'—C6'118.1 (2)
C2—C1—C1'121.6 (2)C2'—C1'—C1121.8 (2)
C6—C1—C1'120.6 (2)C6'—C1'—C1120.1 (2)
C3—C2—C1119.8 (3)C3'—C2'—C1'121.1 (3)
C3—C2—H2120.1C3'—C2'—H2'119.5
C1—C2—H2120.1C1'—C2'—H2'119.5
F1—C3—C2120.2 (3)C2'—C3'—C4'120.0 (3)
F1—C3—C4117.6 (2)C2'—C3'—H3'120.0
C2—C3—C4122.2 (3)C4'—C3'—H3'120.0
C5—C4—C3118.8 (3)C5'—C4'—C3'119.7 (3)
C5—C4—Cl1121.0 (2)C5'—C4'—H4'120.2
C3—C4—Cl1120.2 (2)C3'—C4'—H4'120.2
C4—C5—C6120.1 (3)C6'—C5'—C4'120.4 (3)
C4—C5—H5120.0C6'—C5'—H5'119.8
C6—C5—H5120.0C4'—C5'—H5'119.8
C5—C6—C1121.3 (3)C5'—C6'—C1'120.7 (3)
C5—C6—H6119.4C5'—C6'—H6'119.6
C1—C6—H6119.4C1'—C6'—H6'119.6
C6—C1—C2—C30.9 (4)C2—C1—C1'—C2'31.5 (4)
C1'—C1—C2—C3178.5 (2)C6—C1—C1'—C2'149.1 (3)
C1—C2—C3—F1179.1 (2)C2—C1—C1'—C6'148.9 (3)
C1—C2—C3—C40.2 (4)C6—C1—C1'—C6'30.5 (4)
F1—C3—C4—C5179.8 (3)C6'—C1'—C2'—C3'0.7 (4)
C2—C3—C4—C51.2 (4)C1—C1'—C2'—C3'178.9 (2)
F1—C3—C4—Cl10.4 (4)C1'—C2'—C3'—C4'0.2 (4)
C2—C3—C4—Cl1178.6 (2)C2'—C3'—C4'—C5'0.9 (4)
C3—C4—C5—C61.1 (4)C3'—C4'—C5'—C6'0.6 (4)
Cl1—C4—C5—C6178.8 (2)C4'—C5'—C6'—C1'0.4 (4)
C4—C5—C6—C10.1 (4)C2'—C1'—C6'—C5'1.1 (4)
C2—C1—C6—C51.1 (4)C1—C1'—C6'—C5'178.5 (2)
C1'—C1—C6—C5178.4 (2)
(2F-PCB3) top
Crystal data top
C12H8ClFF(000) = 848
Mr = 206.63Dx = 1.431 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 4148 reflections
a = 17.4184 (17) Åθ = 1.0–27.5°
b = 5.8649 (6) ŵ = 0.36 mm1
c = 19.4400 (19) ÅT = 190 K
β = 104.981 (5)°Prism, colorless
V = 1918.4 (3) Å30.38 × 0.36 × 0.30 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
2192 independent reflections
Radiation source: fine-focus sealed tube1952 reflections with I > 2u(I)
Graphite monochromatorRint = 0.020
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.7°
CCD ϕ and ω scansh = 2222
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
k = 77
Tmin = 0.874, Tmax = 0.899l = 2525
18886 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0376P)2 + 1.2786P]
where P = (Fo2 + 2Fc2)/3
2192 reflections(Δ/σ)max = 0.001
127 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C12H8ClFV = 1918.4 (3) Å3
Mr = 206.63Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.4184 (17) ŵ = 0.36 mm1
b = 5.8649 (6) ÅT = 190 K
c = 19.4400 (19) Å0.38 × 0.36 × 0.30 mm
β = 104.981 (5)°
Data collection top
Nonius KappaCCD
diffractometer
2192 independent reflections
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
1952 reflections with I > 2u(I)
Tmin = 0.874, Tmax = 0.899Rint = 0.020
18886 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.07Δρmax = 0.26 e Å3
2192 reflectionsΔρmin = 0.25 e Å3
127 parameters
Special details top

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

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 (Å2) top
xyzUiso*/Ueq
Cl10.534569 (19)0.53910 (7)0.664773 (16)0.04228 (13)
F10.38354 (5)0.86166 (13)0.42927 (4)0.0375 (2)
C10.33888 (6)0.50333 (19)0.45940 (6)0.0233 (2)
C20.39030 (7)0.6877 (2)0.47656 (6)0.0259 (2)
C30.45045 (7)0.7040 (2)0.53856 (6)0.0287 (3)
H30.48420.83370.54830.034*
C40.45969 (7)0.5239 (2)0.58602 (6)0.0281 (3)
C50.41148 (7)0.3337 (2)0.57200 (6)0.0295 (3)
H50.41890.21120.60500.035*
C60.35197 (7)0.3248 (2)0.50875 (6)0.0263 (2)
H60.31910.19320.49870.032*
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)
H2'0.22320.80180.40580.034*
C3'0.15408 (7)0.6569 (2)0.31581 (6)0.0318 (3)
H3'0.11650.77760.30470.038*
C4'0.14543 (7)0.4679 (2)0.27168 (6)0.0318 (3)
H4'0.10210.45910.23040.038*
C5'0.20028 (7)0.2911 (2)0.28788 (6)0.0311 (3)
H5'0.19470.16180.25760.037*
C6'0.26342 (7)0.3040 (2)0.34856 (6)0.0270 (2)
H6'0.30060.18240.35970.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03151 (18)0.0647 (3)0.02510 (17)0.00510 (15)0.00272 (12)0.00644 (14)
F10.0434 (4)0.0267 (4)0.0386 (4)0.0016 (3)0.0039 (3)0.0083 (3)
C10.0226 (5)0.0261 (6)0.0214 (5)0.0041 (4)0.0060 (4)0.0009 (4)
C20.0302 (6)0.0232 (5)0.0252 (5)0.0036 (4)0.0088 (5)0.0010 (4)
C30.0261 (6)0.0301 (6)0.0295 (6)0.0003 (5)0.0067 (5)0.0064 (5)
C40.0231 (5)0.0399 (7)0.0205 (5)0.0059 (5)0.0044 (4)0.0040 (5)
C50.0289 (6)0.0364 (7)0.0239 (5)0.0053 (5)0.0080 (5)0.0064 (5)
C60.0252 (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) top
Cl1—C41.7381 (12)C1'—C6'1.3961 (16)
F1—C21.3581 (13)C1'—C2'1.3967 (16)
C1—C21.3884 (17)C2'—C3'1.3891 (16)
C1—C61.3986 (16)C2'—H2'0.9500
C1—C1'1.4894 (15)C3'—C4'1.3860 (18)
C2—C31.3809 (16)C3'—H3'0.9500
C3—C41.3841 (17)C4'—C5'1.3896 (18)
C3—H30.9500C4'—H4'0.9500
C4—C51.3800 (18)C5'—C6'1.3914 (16)
C5—C61.3892 (16)C5'—H5'0.9500
C5—H50.9500C6'—H6'0.9500
C6—H60.9500
C2—C1—C6115.95 (10)C6'—C1'—C2'118.85 (10)
C2—C1—C1'122.92 (10)C6'—C1'—C1120.41 (10)
C6—C1—C1'121.13 (10)C2'—C1'—C1120.70 (10)
F1—C2—C3116.89 (10)C3'—C2'—C1'120.38 (11)
F1—C2—C1119.00 (10)C3'—C2'—H2'119.8
C3—C2—C1124.08 (11)C1'—C2'—H2'119.8
C2—C3—C4117.40 (11)C4'—C3'—C2'120.35 (11)
C2—C3—H3121.3C4'—C3'—H3'119.8
C4—C3—H3121.3C2'—C3'—H3'119.8
C5—C4—C3121.67 (10)C3'—C4'—C5'119.88 (11)
C5—C4—Cl1119.69 (9)C3'—C4'—H4'120.1
C3—C4—Cl1118.64 (9)C5'—C4'—H4'120.1
C4—C5—C6118.83 (11)C4'—C5'—C6'119.87 (11)
C4—C5—H5120.6C4'—C5'—H5'120.1
C6—C5—H5120.6C6'—C5'—H5'120.1
C5—C6—C1122.05 (11)C5'—C6'—C1'120.67 (11)
C5—C6—H6119.0C5'—C6'—H6'119.7
C1—C6—H6119.0C1'—C6'—H6'119.7
C6—C1—C2—F1176.62 (10)C2—C1—C1'—C6'129.38 (12)
C1'—C1—C2—F14.19 (16)C6—C1—C1'—C6'51.48 (15)
C6—C1—C2—C31.39 (17)C2—C1—C1'—C2'52.75 (16)
C1'—C1—C2—C3177.80 (10)C6—C1—C1'—C2'126.40 (12)
F1—C2—C3—C4177.77 (10)C6'—C1'—C2'—C3'0.45 (17)
C1—C2—C3—C40.28 (17)C1—C1'—C2'—C3'177.46 (10)
C2—C3—C4—C50.66 (17)C1'—C2'—C3'—C4'0.55 (18)
C2—C3—C4—Cl1179.76 (8)C2'—C3'—C4'—C5'0.13 (19)
C3—C4—C5—C60.42 (17)C3'—C4'—C5'—C6'0.38 (18)
Cl1—C4—C5—C6179.99 (9)C4'—C5'—C6'—C1'0.48 (18)
C4—C5—C6—C10.79 (17)C2'—C1'—C6'—C5'0.06 (17)
C2—C1—C6—C51.63 (16)C1—C1'—C6'—C5'177.98 (10)
C1'—C1—C6—C5177.57 (10)
(2'F-PCB3) top
Crystal data top
C12H8ClFF(000) = 848
Mr = 206.63Dx = 1.412 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 8447 reflections
a = 17.9426 (18) Åθ = 1.0–27.5°
b = 6.0863 (6) ŵ = 0.36 mm1
c = 18.3206 (18) ÅT = 190 K
β = 103.701 (5)°Prism, colorless
V = 1943.8 (3) Å30.44 × 0.38 × 0.30 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
2217 independent reflections
Radiation source: fine-focus sealed tube1708 reflections with I > 2u(I)
Graphite monochromatorRint = 0.030
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.6°
CCD ϕ and ω scansh = 2223
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
k = 77
Tmin = 0.858, Tmax = 0.900l = 2323
32179 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6778P]
where P = (Fo2 + 2Fc2)/3
2217 reflections(Δ/σ)max = 0.012
131 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.26 e Å3
Crystal data top
C12H8ClFV = 1943.8 (3) Å3
Mr = 206.63Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.9426 (18) ŵ = 0.36 mm1
b = 6.0863 (6) ÅT = 190 K
c = 18.3206 (18) Å0.44 × 0.38 × 0.30 mm
β = 103.701 (5)°
Data collection top
Nonius KappaCCD
diffractometer
2217 independent reflections
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
1708 reflections with I > 2u(I)
Tmin = 0.858, Tmax = 0.900Rint = 0.030
32179 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.097H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å3
2217 reflectionsΔρmin = 0.26 e Å3
131 parameters
Special details top

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

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.10919 (2)0.43861 (8)0.22489 (2)0.05558 (17)
C10.30638 (7)0.5057 (2)0.42933 (7)0.0281 (3)
C20.25507 (8)0.6791 (2)0.40648 (8)0.0317 (3)
H20.26210.81270.43410.038*
C30.19403 (8)0.6592 (2)0.34411 (8)0.0359 (3)
H30.15900.77710.32940.043*
C40.18498 (8)0.4652 (2)0.30378 (8)0.0351 (3)
C50.23510 (8)0.2920 (2)0.32435 (8)0.0368 (3)
H50.22840.16000.29590.044*
C60.29539 (8)0.3130 (2)0.38717 (8)0.0331 (3)
H60.32990.19370.40170.040*
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)
F10.40804 (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)
H3'0.50970.84660.58400.048*
C4'0.49120 (8)0.5478 (3)0.62725 (9)0.0403 (4)
H4'0.53200.55620.67090.048*
C5'0.44443 (8)0.3644 (3)0.61447 (8)0.0381 (4)
H5'0.45320.24670.64960.046*
C6'0.38487 (8)0.3512 (2)0.55077 (8)0.0333 (3)0.9774 (16)
H6'0.35340.22370.54280.040*0.9774 (16)
C2"0.38487 (8)0.3512 (2)0.55077 (8)0.0333 (3)0.0226 (16)
F20.3398 (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"0.41030.81930.47840.038*0.0226 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0481 (3)0.0746 (3)0.0349 (2)0.0194 (2)0.00848 (17)0.00921 (19)
C10.0267 (6)0.0307 (7)0.0278 (7)0.0006 (5)0.0084 (5)0.0021 (5)
C20.0325 (7)0.0314 (7)0.0309 (7)0.0036 (5)0.0066 (6)0.0001 (6)
C30.0307 (7)0.0407 (8)0.0356 (8)0.0047 (6)0.0067 (6)0.0084 (6)
C40.0315 (7)0.0461 (9)0.0261 (6)0.0086 (6)0.0037 (5)0.0039 (6)
C50.0400 (8)0.0378 (8)0.0332 (7)0.0074 (6)0.0098 (6)0.0067 (6)
C60.0333 (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)
F10.0452 (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) top
Cl1—C41.7417 (14)C1'—C2'1.3879 (19)
C1—C61.3922 (19)C1'—C6'1.4008 (19)
C1—C21.3981 (19)C2'—F11.3613 (15)
C1—C1'1.4850 (18)C2'—C3'1.3750 (19)
C2—C31.3881 (18)C3'—C4'1.387 (2)
C2—H20.9500C3'—H3'0.9500
C3—C41.382 (2)C4'—C5'1.383 (2)
C3—H30.9500C4'—H4'0.9500
C4—C51.379 (2)C5'—C6'1.3855 (19)
C5—C61.3861 (19)C5'—H5'0.9500
C5—H50.9500C6'—H6'0.9500
C6—H60.9500C2"—F21.360
C6—C1—C2118.23 (12)C2'—C1'—C6'115.68 (12)
C6—C1—C1'120.16 (11)C2'—C1'—C1122.94 (12)
C2—C1—C1'121.59 (12)C6'—C1'—C1121.37 (12)
C3—C2—C1121.05 (13)F1—C2'—C3'117.55 (12)
C3—C2—H2119.5F1—C2'—C1'118.29 (11)
C1—C2—H2119.5C3'—C2'—C1'124.15 (13)
C4—C3—C2118.99 (13)C2'—C3'—C4'118.55 (13)
C4—C3—H3120.5C2'—C3'—H3'120.7
C2—C3—H3120.5C4'—C3'—H3'120.7
C5—C4—C3121.38 (12)C5'—C4'—C3'119.68 (13)
C5—C4—Cl1119.09 (11)C5'—C4'—H4'120.2
C3—C4—Cl1119.53 (11)C3'—C4'—H4'120.2
C4—C5—C6119.11 (13)C4'—C5'—C6'120.35 (13)
C4—C5—H5120.4C4'—C5'—H5'119.8
C6—C5—H5120.4C6'—C5'—H5'119.8
C5—C6—C1121.24 (13)C5'—C6'—C1'121.58 (13)
C5—C6—H6119.4C5'—C6'—H6'119.2
C1—C6—H6119.4C1'—C6'—H6'119.2
C6—C1—C2—C31.0 (2)C2—C1—C1'—C6'133.14 (14)
C1'—C1—C2—C3177.33 (12)C6'—C1'—C2'—F1178.39 (12)
C1—C2—C3—C40.9 (2)C1—C1'—C2'—F10.80 (19)
C2—C3—C4—C50.1 (2)C6'—C1'—C2'—C3'0.3 (2)
C2—C3—C4—Cl1179.41 (10)C1—C1'—C2'—C3'179.54 (13)
C3—C4—C5—C60.5 (2)F1—C2'—C3'—C4'178.49 (13)
Cl1—C4—C5—C6179.95 (11)C1'—C2'—C3'—C4'0.3 (2)
C4—C5—C6—C10.4 (2)C2'—C3'—C4'—C5'0.1 (2)
C2—C1—C6—C50.3 (2)C3'—C4'—C5'—C6'0.1 (2)
C1'—C1—C6—C5178.00 (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) top
Crystal data top
C12H8ClFF(000) = 424
Mr = 206.63Dx = 1.432 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 3738 reflections
a = 11.3527 (11) Åθ = 1.0–27.5°
b = 3.9099 (4) ŵ = 0.36 mm1
c = 21.920 (2) ÅT = 190 K
β = 99.966 (5)°Prism, colorless
V = 958.30 (16) Å30.40 × 0.12 × 0.12 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1679 independent reflections
Radiation source: fine-focus sealed tube1430 reflections with I > 2u(I)
Graphite monochromatorRint = 0.032
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 3.1°
CCD ϕ and ω scansh = 1313
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
k = 34
Tmin = 0.868, Tmax = 0.958l = 2526
14766 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0414P)2 + 0.4269P]
where P = (Fo2 + 2Fc2)/3
1679 reflections(Δ/σ)max = 0.002
167 parametersΔρmax = 0.21 e Å3
45 restraintsΔρmin = 0.25 e Å3
Crystal data top
C12H8ClFV = 958.30 (16) Å3
Mr = 206.63Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.3527 (11) ŵ = 0.36 mm1
b = 3.9099 (4) ÅT = 190 K
c = 21.920 (2) Å0.40 × 0.12 × 0.12 mm
β = 99.966 (5)°
Data collection top
Nonius KappaCCD
diffractometer
1679 independent reflections
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
1430 reflections with I > 2u(I)
Tmin = 0.868, Tmax = 0.958Rint = 0.032
14766 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03845 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.09Δρmax = 0.21 e Å3
1679 reflectionsΔρmin = 0.25 e Å3
167 parameters
Special details top

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

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.66327 (5)0.32613 (16)0.85208 (2)0.0535 (2)0.874 (3)
C10.41986 (18)0.0321 (8)0.67357 (9)0.0339 (5)0.874 (3)
C20.5279 (3)0.1966 (17)0.67294 (9)0.0379 (5)0.874 (3)
H20.55100.24800.63430.045*0.874 (3)
C30.6031 (4)0.2878 (17)0.72722 (9)0.0391 (5)0.874 (3)
H30.67650.40210.72580.047*0.874 (3)
C40.5699 (2)0.2102 (8)0.78339 (9)0.0382 (5)0.874 (3)
C50.4640 (3)0.0421 (14)0.78585 (10)0.0395 (7)0.874 (3)
H50.44250.01340.82470.047*0.874 (3)
C60.3895 (3)0.0445 (12)0.73142 (10)0.0368 (9)0.874 (3)
H60.31620.15840.73320.044*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)
H2'0.47020.17110.56430.050*0.874 (3)
C3'0.3082 (2)0.2663 (14)0.51095 (12)0.0466 (6)0.874 (3)
F10.35685 (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)
H4'0.13660.34060.46920.058*0.874 (3)
C5'0.1403 (2)0.1653 (8)0.55760 (12)0.0485 (6)0.874 (3)
H5'0.05620.16210.55590.058*0.874 (3)
C6'0.2150 (2)0.0664 (7)0.61103 (11)0.0416 (5)0.874 (3)
H6'0.18120.00420.64570.050*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*0.56120.25940.63370.045*0.126 (3)
C3*0.609 (2)0.295 (11)0.72697 (13)0.0391 (5)0.126 (3)
H3*0.67980.42370.72670.047*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*0.45010.04720.82150.047*0.126 (3)
C6*0.403 (2)0.081 (10)0.7279 (4)0.0368 (9)0.126 (3)
H6*0.33220.21050.72860.044*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"0.19640.05140.64250.050*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"0.15800.35060.46340.058*0.126 (3)
C5"0.3321 (9)0.273 (10)0.5048 (6)0.0466 (6)0.126 (3)
H5"0.36700.32960.46970.056*0.126 (3)
C6"0.4043 (8)0.178 (9)0.5593 (6)0.0417 (5)0.126 (3)
H6"0.48850.17070.56110.050*0.126 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0599 (3)0.0554 (4)0.0424 (3)0.0035 (3)0.0006 (2)0.0025 (2)
C10.0376 (10)0.0277 (11)0.0381 (10)0.0083 (9)0.0116 (8)0.0013 (8)
C20.0409 (12)0.0374 (11)0.0380 (10)0.0048 (11)0.0145 (8)0.0055 (9)
C30.0368 (10)0.0357 (12)0.0460 (11)0.0002 (9)0.0099 (8)0.0054 (9)
C40.0426 (10)0.0345 (11)0.0372 (10)0.0071 (8)0.0061 (8)0.0005 (8)
C50.0477 (12)0.0371 (15)0.0374 (10)0.0061 (12)0.0174 (8)0.0021 (9)
C60.0366 (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)
F10.0726 (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) top
Cl1—C41.7447 (19)C1*—C2*1.387 (3)
C1—C21.388 (3)C1*—C6*1.403 (3)
C1—C61.403 (3)C1*—C1"1.485 (3)
C1—C1'1.485 (3)C2*—C3*1.386 (3)
C2—C31.385 (3)C2*—H2*0.9500
C2—H20.9500C3*—C4*1.382 (3)
C3—C41.382 (3)C3*—H3*0.9500
C3—H30.9500C4*—C5*1.380 (3)
C4—C51.380 (3)C5*—C6*1.379 (3)
C5—C61.380 (3)C5*—H5*0.9500
C5—H50.9500C6*—H6*0.9500
C6—H60.9500C1"—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'—H2'0.9500C3"—C4"1.361 (4)
C3'—C4'1.361 (4)C3"—F1"1.373 (3)
C3'—F11.374 (3)C4"—C5"1.388 (4)
C4'—C5'1.388 (4)C4"—H4"0.9500
C4'—H4'0.9500C5"—C6"1.377 (4)
C5'—C6'1.377 (3)C5"—H5"0.9500
C5'—H5'0.9500C6"—H6"0.9500
C6'—H6'0.9500
C2—C1—C6117.64 (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—C1121.67 (17)C6*—C1*—C1"120.4 (2)
C3—C2—H2119.2C3*—C2*—C1*121.7 (2)
C1—C2—H2119.2C3*—C2*—H2*119.2
C4—C3—C2119.08 (18)C1*—C2*—H2*119.2
C4—C3—H3120.5C4*—C3*—C2*119.1 (2)
C2—C3—H3120.5C4*—C3*—H3*120.5
C5—C4—C3120.88 (18)C2*—C3*—H3*120.5
C5—C4—Cl1119.57 (15)C5*—C4*—C3*120.9 (2)
C3—C4—Cl1119.55 (15)C6*—C5*—C4*119.4 (2)
C6—C5—C4119.40 (17)C6*—C5*—H5*120.3
C6—C5—H5120.3C4*—C5*—H5*120.3
C4—C5—H5120.3C5*—C6*—C1*121.3 (2)
C5—C6—C1121.32 (17)C5*—C6*—H6*119.4
C5—C6—H6119.3C1*—C6*—H6*119.4
C1—C6—H6119.3C6"—C1"—C2"117.9 (2)
C6'—C1'—C2'117.85 (18)C6"—C1"—C1*121.8 (2)
C6'—C1'—C1121.60 (19)C2"—C1"—C1*120.3 (2)
C2'—C1'—C1120.55 (18)C3"—C2"—C1"118.5 (3)
C3'—C2'—C1'118.6 (2)C3"—C2"—H2"120.7
C3'—C2'—H2'120.7C1"—C2"—H2"120.7
C1'—C2'—H2'120.7C4"—C3"—F1"118.5 (3)
C4'—C3'—F1118.4 (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'—H4'121.4C5"—C4"—H4"121.4
C5'—C4'—H4'121.4C6"—C5"—C4"120.5 (3)
C6'—C5'—C4'120.5 (2)C6"—C5"—H5"119.8
C6'—C5'—H5'119.8C4"—C5"—H5"119.8
C4'—C5'—H5'119.8C5"—C6"—C1"121.6 (3)
C5'—C6'—C1'121.6 (2)C5"—C6"—H6"119.2
C5'—C6'—H6'119.2C1"—C6"—H6"119.2
C6—C1—C2—C31.0 (3)C1—C1'—C6'—C5'178.7 (2)
C1'—C1—C2—C3179.7 (2)C6*—C1*—C2*—C3*0.0 (6)
C1—C2—C3—C40.5 (4)C1"—C1*—C2*—C3*178.9 (5)
C2—C3—C4—C50.5 (4)C1*—C2*—C3*—C4*0.0 (6)
C2—C3—C4—Cl1179.6 (2)C2*—C3*—C4*—C5*0.0 (14)
C3—C4—C5—C61.0 (4)C3*—C4*—C5*—C6*0.0 (18)
Cl1—C4—C5—C6179.0 (2)C4*—C5*—C6*—C1*0.0 (18)
C4—C5—C6—C10.6 (4)C2*—C1*—C6*—C5*0.0 (14)
C2—C1—C6—C50.4 (4)C1"—C1*—C6*—C5*178.9 (10)
C1'—C1—C6—C5179.2 (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'—F1178.9 (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) top
Crystal data top
C12H8ClFF(000) = 848
Mr = 206.63Dx = 1.403 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 8447 reflections
a = 9.550 (1) Åθ = 1.0–27.5°
b = 13.1441 (13) ŵ = 0.36 mm1
c = 15.6777 (16) ÅT = 190 K
β = 96.323 (5)°Prism, colorless
V = 1956.0 (3) Å30.39 × 0.24 × 0.14 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
3447 independent reflections
Radiation source: fine-focus sealed tube2412 reflections with I > 2u(I)
Graphite monochromatorRint = 0.038
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.9°
CCD ϕ and ω scansh = 1111
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
k = 1515
Tmin = 0.873, Tmax = 0.952l = 1818
32179 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.3255P]
where P = (Fo2 + 2Fc2)/3
3447 reflections(Δ/σ)max < 0.001
326 parametersΔρmax = 0.17 e Å3
86 restraintsΔρmin = 0.32 e Å3
Crystal data top
C12H8ClFV = 1956.0 (3) Å3
Mr = 206.63Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.550 (1) ŵ = 0.36 mm1
b = 13.1441 (13) ÅT = 190 K
c = 15.6777 (16) Å0.39 × 0.24 × 0.14 mm
β = 96.323 (5)°
Data collection top
Nonius KappaCCD
diffractometer
3447 independent reflections
Absorption correction: multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
2412 reflections with I > 2u(I)
Tmin = 0.873, Tmax = 0.952Rint = 0.038
32179 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04186 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.06Δρmax = 0.17 e Å3
3447 reflectionsΔρmin = 0.32 e Å3
326 parameters
Special details top

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

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.63996 (6)0.59936 (4)0.64831 (4)0.0567 (2)0.841 (3)
F10.59225 (14)0.16982 (9)0.59803 (8)0.0843 (5)0.841 (3)
C10.6210 (3)0.25429 (17)0.62815 (16)0.0302 (5)0.841 (3)
C20.6207 (4)0.30324 (18)0.70725 (16)0.0353 (5)0.841 (3)
H20.61650.26370.75760.042*0.841 (3)
C30.6265 (4)0.40839 (18)0.71372 (17)0.0396 (6)0.841 (3)
H30.62590.44060.76790.047*0.841 (3)
C40.6331 (5)0.46547 (18)0.64080 (17)0.0369 (5)0.841 (3)
C50.6347 (5)0.42005 (19)0.56213 (17)0.0394 (6)0.841 (3)
H50.64060.46040.51240.047*0.841 (3)
C60.6277 (5)0.31502 (18)0.55552 (17)0.0362 (5)0.841 (3)
H60.62760.28380.50080.043*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)
H2'0.47540.11890.70890.046*0.841 (3)
C3'0.5190 (4)0.0194 (2)0.6610 (2)0.0475 (6)0.841 (3)
H3'0.45950.05750.69370.057*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)
H5'0.73980.04890.51860.062*0.841 (3)
C6'0.6907 (4)0.09043 (19)0.5637 (2)0.0407 (6)0.841 (3)
H6'0.74830.12790.52930.049*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*0.48440.14920.71540.046*0.159 (3)
C3*0.528 (2)0.0114 (5)0.6670 (11)0.0475 (6)0.159 (3)
H3*0.47120.02690.70150.057*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*0.73120.01610.51570.062*0.159 (3)
C6*0.690 (3)0.1226 (5)0.5648 (14)0.0407 (6)0.159 (3)
H6*0.74570.16010.52920.049*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'*0.62420.29560.76100.042*0.159 (3)
C3'*0.632 (2)0.4398 (4)0.7165 (5)0.0396 (6)0.159 (3)
H3'*0.63310.47240.77060.047*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'*0.62710.49170.51320.047*0.159 (3)
C6'*0.628 (3)0.3466 (5)0.5584 (6)0.0362 (5)0.159 (3)
H6'*0.63000.31490.50410.043*0.159 (3)
Cl20.13834 (8)0.85674 (5)0.63520 (4)0.0680 (3)0.841 (3)
F20.10814 (12)0.08459 (8)0.61270 (8)0.0698 (5)0.841 (3)
C1A0.1283 (3)0.51280 (19)0.6285 (2)0.0328 (5)0.841 (3)
C2A0.2492 (3)0.5654 (2)0.6627 (3)0.0395 (6)0.841 (3)
H2A0.33030.52810.68490.047*0.841 (3)
C3A0.2527 (3)0.6701 (2)0.6649 (3)0.0442 (6)0.841 (3)
H3A0.33530.70480.68840.053*0.841 (3)
C4A0.1340 (3)0.7241 (2)0.6323 (3)0.0430 (6)0.841 (3)
C5A0.0135 (3)0.6750 (2)0.5984 (3)0.0415 (7)0.841 (3)
H5A0.06730.71280.57650.050*0.841 (3)
C6A0.0113 (3)0.5698 (2)0.5966 (3)0.0374 (6)0.841 (3)
H6A0.07190.53580.57320.045*0.841 (3)
C1'A0.1247 (3)0.40065 (19)0.6249 (2)0.0330 (5)0.841 (3)
C2'A0.2402 (3)0.3450 (2)0.6031 (3)0.0378 (6)0.841 (3)
H2'A0.32320.38000.59180.045*0.841 (3)
C3'A0.2362 (3)0.2401 (2)0.5977 (3)0.0427 (6)0.841 (3)
H3'A0.31460.20310.58160.051*0.841 (3)
C4'A0.1169 (3)0.19045 (19)0.6161 (4)0.0429 (6)0.841 (3)
C5'A0.0018 (3)0.2413 (2)0.6401 (3)0.0438 (7)0.841 (3)
H5'A0.07850.20510.65430.053*0.841 (3)
C6'A0.0054 (3)0.34586 (19)0.6430 (3)0.0372 (6)0.841 (3)
H6'A0.07490.38190.65760.045*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*0.32980.40380.59850.045*0.159 (3)
C3A*0.2382 (14)0.2659 (5)0.6032 (19)0.0427 (6)0.159 (3)
H3A*0.31720.22780.58940.051*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*0.08970.23750.63830.053*0.159 (3)
C6A*0.0056 (16)0.3763 (5)0.639 (2)0.0372 (6)0.159 (3)
H6A*0.07440.41380.65230.045*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"0.33430.55480.68720.047*0.159 (3)
C3A"0.2592 (13)0.6974 (5)0.6652 (16)0.0442 (6)0.159 (3)
H3A"0.34100.73200.69020.053*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"0.05260.74170.56600.050*0.159 (3)
C6A"0.0192 (18)0.5989 (6)0.594 (2)0.0374 (6)0.159 (3)
H6A"0.06470.56560.57020.045*0.159 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0460 (4)0.0385 (4)0.0862 (5)0.0013 (3)0.0096 (3)0.0024 (3)
F10.1177 (11)0.0473 (8)0.0849 (10)0.0040 (7)0.0028 (8)0.0082 (6)
C10.0285 (10)0.0270 (14)0.0357 (11)0.0001 (13)0.0059 (8)0.0017 (10)
C20.0381 (11)0.0370 (15)0.0316 (11)0.0004 (15)0.0076 (9)0.0009 (11)
C30.0387 (12)0.0340 (16)0.0464 (13)0.0001 (15)0.0067 (9)0.0093 (11)
C40.0261 (11)0.0277 (14)0.0573 (14)0.0016 (18)0.0060 (9)0.0001 (11)
C50.0348 (12)0.0358 (16)0.0478 (13)0.000 (2)0.0057 (9)0.0101 (11)
C60.0361 (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)
Cl20.0943 (6)0.0461 (4)0.0695 (5)0.0107 (3)0.0354 (4)0.0014 (3)
F20.0776 (8)0.0488 (8)0.0835 (9)0.0083 (6)0.0111 (6)0.0036 (6)
C1A0.0337 (11)0.0373 (14)0.0284 (10)0.0005 (11)0.0076 (8)0.0046 (13)
C2A0.0347 (11)0.0451 (15)0.0395 (11)0.0017 (12)0.0076 (9)0.0044 (16)
C3A0.0482 (13)0.0437 (17)0.0424 (12)0.0100 (12)0.0129 (10)0.0055 (16)
C4A0.0636 (15)0.0330 (14)0.0361 (12)0.0050 (13)0.0224 (12)0.0005 (17)
C5A0.0520 (14)0.0404 (17)0.0328 (13)0.0044 (13)0.0080 (11)0.0029 (16)
C6A0.0390 (12)0.0393 (15)0.0336 (12)0.0016 (13)0.0025 (10)0.0042 (19)
C1'A0.0321 (11)0.0380 (14)0.0282 (10)0.0007 (12)0.0003 (8)0.0054 (14)
C2'A0.0301 (11)0.0429 (16)0.0409 (13)0.0014 (11)0.0059 (9)0.0043 (15)
C3'A0.0379 (12)0.0430 (16)0.0469 (14)0.0070 (12)0.0030 (10)0.0037 (18)
C4'A0.0497 (13)0.0314 (15)0.0465 (13)0.0025 (13)0.0007 (10)0.004 (2)
C5'A0.0395 (12)0.0436 (16)0.0482 (17)0.0081 (13)0.0041 (11)0.003 (2)
C6'A0.0290 (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) top
Cl1—C41.765 (2)Cl2—C4A1.744 (3)
F1—C4'1.360 (3)F2—C4'A1.395 (3)
C1—C21.397 (3)C1A—C6A1.392 (3)
C1—C61.398 (3)C1A—C2A1.401 (3)
C1—C1'1.479 (3)C1A—C1'A1.475 (3)
C2—C31.387 (3)C2A—C3A1.377 (3)
C2—H20.9500C2A—H2A0.9500
C3—C41.375 (3)C3A—C4A1.386 (4)
C3—H30.9500C3A—H3A0.9500
C4—C51.372 (3)C4A—C5A1.374 (3)
C5—C61.385 (3)C5A—C6A1.383 (3)
C5—H50.9500C5A—H5A0.9500
C6—H60.9500C6A—H6A0.9500
C1'—C2'1.394 (3)C1'A—C2'A1.397 (3)
C1'—C6'1.395 (3)C1'A—C6'A1.403 (3)
C2'—C3'1.383 (3)C2'A—C3'A1.381 (3)
C2'—H2'0.9500C2'A—H2'A0.9500
C3'—C4'1.366 (4)C3'A—C4'A1.371 (3)
C3'—H3'0.9500C3'A—H3'A0.9500
C4'—C5'1.378 (4)C4'A—C5'A1.374 (3)
C5'—C6'1.379 (3)C5'A—C6'A1.375 (3)
C5'—H5'0.9500C5'A—H5'A0.9500
C6'—H6'0.9500C6'A—H6'A0.9500
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*0.9500C2A*—H2A*0.9500
C3*—C4*1.376 (5)C3A*—C4A*1.388 (6)
C3*—H3*0.9500C3A*—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*0.9500C5A*—H5A*0.9500
C6*—H6*0.9500C6A*—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'*0.9500C2A"—H2A"0.9500
C3'*—C4'*1.365 (6)C3A"—C4A"1.371 (5)
C3'*—H3'*0.9500C3A"—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'*0.9500C5A"—H5A"0.9500
C6'*—H6'*0.9500C6A"—H6A"0.9500
C2—C1—C6117.7 (2)C6A—C1A—C2A117.8 (2)
C2—C1—C1'121.6 (2)C6A—C1A—C1'A120.7 (2)
C6—C1—C1'120.7 (2)C2A—C1A—C1'A121.5 (2)
C3—C2—C1121.3 (2)C3A—C2A—C1A121.3 (2)
C3—C2—H2119.3C3A—C2A—H2A119.4
C1—C2—H2119.3C1A—C2A—H2A119.4
C4—C3—C2119.2 (2)C2A—C3A—C4A119.1 (2)
C4—C3—H3120.4C2A—C3A—H3A120.4
C2—C3—H3120.4C4A—C3A—H3A120.4
C5—C4—C3121.1 (2)C5A—C4A—C3A121.2 (2)
C5—C4—Cl1119.34 (19)C5A—C4A—Cl2119.7 (2)
C3—C4—Cl1119.57 (18)C3A—C4A—Cl2119.1 (2)
C4—C5—C6119.7 (2)C4A—C5A—C6A119.2 (2)
C4—C5—H5120.1C4A—C5A—H5A120.4
C6—C5—H5120.1C6A—C5A—H5A120.4
C5—C6—C1120.9 (2)C5A—C6A—C1A121.4 (2)
C5—C6—H6119.5C5A—C6A—H6A119.3
C1—C6—H6119.5C1A—C6A—H6A119.3
C2'—C1'—C6'118.0 (2)C2'A—C1'A—C6'A117.5 (2)
C2'—C1'—C1121.1 (2)C2'A—C1'A—C1A121.2 (2)
C6'—C1'—C1120.8 (2)C6'A—C1'A—C1A121.4 (2)
C3'—C2'—C1'121.1 (2)C3'A—C2'A—C1'A121.4 (2)
C3'—C2'—H2'119.4C3'A—C2'A—H2'A119.3
C1'—C2'—H2'119.4C1'A—C2'A—H2'A119.3
C4'—C3'—C2'118.7 (2)C4'A—C3'A—C2'A118.7 (2)
C4'—C3'—H3'120.7C4'A—C3'A—H3'A120.7
C2'—C3'—H3'120.7C2'A—C3'A—H3'A120.7
F1—C4'—C3'119.2 (2)C3'A—C4'A—C5'A122.3 (2)
F1—C4'—C5'118.4 (2)C3'A—C4'A—F2121.0 (2)
C3'—C4'—C5'122.4 (2)C5'A—C4'A—F2116.7 (2)
C4'—C5'—C6'118.4 (2)C4'A—C5'A—C6'A118.5 (2)
C4'—C5'—H5'120.8C4'A—C5'A—H5'A120.7
C6'—C5'—H5'120.8C6'A—C5'A—H5'A120.7
C5'—C6'—C1'121.4 (2)C5'A—C6'A—C1'A121.6 (2)
C5'—C6'—H6'119.3C5'A—C6'A—H6'A119.2
C1'—C6'—H6'119.3C1'A—C6'A—H6'A119.2
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*119.3C3A*—C2A*—H2A*119.3
C1*—C2*—H2*119.3C1A*—C2A*—H2A*119.3
C4*—C3*—C2*119.3 (4)C2A*—C3A*—C4A*119.2 (4)
C4*—C3*—H3*120.3C2A*—C3A*—H3A*120.4
C2*—C3*—H3*120.3C4A*—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*120.2C4A*—C5A*—H5A*120.4
C6*—C5*—H5*120.2C6A*—C5A*—H5A*120.4
C5*—C6*—C1*121.1 (4)C5A*—C6A*—C1A*121.5 (4)
C5*—C6*—H6*119.5C5A*—C6A*—H6A*119.2
C1*—C6*—H6*119.5C1A*—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'*119.4C3A"—C2A"—H2A"119.2
C1'*—C2'*—H2'*119.4C1A"—C2A"—H2A"119.2
C4'*—C3'*—C2'*118.9 (4)C4A"—C3A"—C2A"118.8 (4)
C4'*—C3'*—H3'*120.5C4A"—C3A"—H3A"120.6
C2'*—C3'*—H3'*120.5C2A"—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'*120.8C6A"—C5A"—H5A"120.6
C4'*—C5'*—H5'*120.8C4A"—C5A"—H5A"120.6
C5'*—C6'*—C1'*121.5 (4)C5A"—C6A"—C1A"121.7 (4)
C5'*—C6'*—H6'*119.3C5A"—C6A"—H6A"119.1
C1'*—C6'*—H6'*119.3C1A"—C6A"—H6A"119.1
C6—C1—C2—C30.2 (4)C6A—C1A—C2A—C3A0.1 (4)
C1'—C1—C2—C3179.5 (3)C1'A—C1A—C2A—C3A179.1 (3)
C1—C2—C3—C40.3 (4)C1A—C2A—C3A—C4A0.1 (4)
C2—C3—C4—C50.3 (6)C2A—C3A—C4A—C5A0.3 (6)
C2—C3—C4—Cl1179.8 (3)C2A—C3A—C4A—Cl2179.9 (3)
C3—C4—C5—C60.8 (7)C3A—C4A—C5A—C6A0.3 (7)
Cl1—C4—C5—C6179.3 (4)Cl2—C4A—C5A—C6A179.9 (4)
C4—C5—C6—C10.8 (7)C4A—C5A—C6A—C1A0.1 (7)
C2—C1—C6—C50.3 (6)C2A—C1A—C6A—C5A0.1 (6)
C1'—C1—C6—C5179.9 (4)C1'A—C1A—C6A—C5A179.1 (4)
C2—C1—C1'—C2'39.0 (4)C6A—C1A—C1'A—C2'A139.0 (4)
C6—C1—C1'—C2'140.7 (4)C2A—C1A—C1'A—C2'A40.2 (4)
C2—C1—C1'—C6'142.1 (4)C6A—C1A—C1'A—C6'A40.9 (5)
C6—C1—C1'—C6'38.1 (5)C2A—C1A—C1'A—C6'A139.9 (4)
C6'—C1'—C2'—C3'0.4 (4)C6'A—C1'A—C2'A—C3'A1.4 (4)
C1—C1'—C2'—C3'178.5 (3)C1A—C1'A—C2'A—C3'A178.5 (3)
C1'—C2'—C3'—C4'0.9 (4)C1'A—C2'A—C3'A—C4'A1.5 (5)
C2'—C3'—C4'—F1178.0 (3)C2'A—C3'A—C4'A—C5'A0.3 (7)
C2'—C3'—C4'—C5'0.0 (6)C2'A—C3'A—C4'A—F2179.2 (4)
F1—C4'—C5'—C6'179.5 (5)C3'A—C4'A—C5'A—C6'A2.1 (8)
C3'—C4'—C5'—C6'1.5 (8)F2—C4'A—C5'A—C6'A179.0 (5)
C4'—C5'—C6'—C1'2.0 (8)C4'A—C5'A—C6'A—C1'A2.1 (8)
C2'—C1'—C6'—C5'1.1 (6)C2'A—C1'A—C6'A—C5'A0.4 (6)
C1—C1'—C6'—C5'180.0 (4)C1A—C1'A—C6'A—C5'A179.7 (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)

Experimental details

(3F-PCB3)(2F-PCB3)(2'F-PCB3)(3'F-PCB3)
Crystal data
Chemical formulaC12H8ClFC12H8ClFC12H8ClFC12H8ClF
Mr206.63206.63206.63206.63
Crystal system, space groupOrthorhombic, PbcaMonoclinic, C2/cMonoclinic, C2/cMonoclinic, P21/n
Temperature (K)190190190190
a, b, c (Å)11.9836 (7), 7.3820 (12), 21.670 (2)17.4184 (17), 5.8649 (6), 19.4400 (19)17.9426 (18), 6.0863 (6), 18.3206 (18)11.3527 (11), 3.9099 (4), 21.920 (2)
α, β, γ (°)90, 90, 9090, 104.981 (5), 9090, 103.701 (5), 9090, 99.966 (5), 90
V3)1917.0 (4)1918.4 (3)1943.8 (3)958.30 (16)
Z8884
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.360.360.360.36
Crystal size (mm)0.35 × 0.08 × 0.070.38 × 0.36 × 0.300.44 × 0.38 × 0.300.40 × 0.12 × 0.12
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
Multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
Multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
Multi-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
Tmin, Tmax0.883, 0.9750.874, 0.8990.858, 0.9000.868, 0.958
No. of measured, independent and
observed [I > 2u(I)] reflections
34729, 1691, 1367 18886, 2192, 1952 32179, 2217, 1708 14766, 1679, 1430
Rint0.0500.0200.0300.032
(sin θ/λ)max1)0.5950.6500.6500.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.144, 1.06 0.030, 0.083, 1.07 0.034, 0.097, 1.05 0.038, 0.098, 1.09
No. of reflections1691219222171679
No. of parameters127127131167
No. of restraints00145
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.300.26, 0.250.20, 0.260.21, 0.25


(4'F-PCB3)
Crystal data
Chemical formulaC12H8ClF
Mr206.63
Crystal system, space groupMonoclinic, P21/n
Temperature (K)190
a, b, c (Å)9.550 (1), 13.1441 (13), 15.6777 (16)
α, β, γ (°)90, 96.323 (5), 90
V3)1956.0 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.39 × 0.24 × 0.14
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
HKL SCALEPACK (Otwinowski & Minor, 1997)
Tmin, Tmax0.873, 0.952
No. of measured, independent and
observed [I > 2u(I)] reflections
32179, 3447, 2412
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.111, 1.06
No. of reflections3447
No. of parameters326
No. of restraints86
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.32

Computer programs: Collect (Nonius BV, 1997-2000), Collect (Nonius BV, 1997 - 2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997, SHELXTL v6.1 (Sheldrick, 2001), SHELXTL v6.1 (Sheldrick, 1997).

Selected geometric parameters (Å, º) for (3F-PCB3) top
Cl1—C41.733 (3)C5—C61.384 (4)
F1—C31.341 (3)C1'—C2'1.392 (4)
C1—C21.394 (4)C1'—C6'1.404 (4)
C1—C61.400 (4)C2'—C3'1.386 (4)
C1—C1'1.488 (4)C3'—C4'1.386 (4)
C2—C31.373 (4)C4'—C5'1.383 (4)
C3—C41.377 (4)C5'—C6'1.380 (4)
C4—C51.375 (4)
C2—C1—C6117.8 (2)C4—C5—C6120.1 (3)
C2—C1—C1'121.6 (2)C5—C6—C1121.3 (3)
C6—C1—C1'120.6 (2)C2'—C1'—C6'118.1 (2)
C3—C2—C1119.8 (3)C2'—C1'—C1121.8 (2)
F1—C3—C2120.2 (3)C6'—C1'—C1120.1 (2)
F1—C3—C4117.6 (2)C3'—C2'—C1'121.1 (3)
C2—C3—C4122.2 (3)C2'—C3'—C4'120.0 (3)
C5—C4—C3118.8 (3)C5'—C4'—C3'119.7 (3)
C5—C4—Cl1121.0 (2)C6'—C5'—C4'120.4 (3)
C3—C4—Cl1120.2 (2)C5'—C6'—C1'120.7 (3)
Selected geometric parameters (Å, º) for (2F-PCB3) top
Cl1—C41.7381 (12)C5—C61.3892 (16)
F1—C21.3581 (13)C1'—C6'1.3961 (16)
C1—C21.3884 (17)C1'—C2'1.3967 (16)
C1—C61.3986 (16)C2'—C3'1.3891 (16)
C1—C1'1.4894 (15)C3'—C4'1.3860 (18)
C2—C31.3809 (16)C4'—C5'1.3896 (18)
C3—C41.3841 (17)C5'—C6'1.3914 (16)
C4—C51.3800 (18)
C2—C1—C6115.95 (10)C4—C5—C6118.83 (11)
C2—C1—C1'122.92 (10)C5—C6—C1122.05 (11)
C6—C1—C1'121.13 (10)C6'—C1'—C2'118.85 (10)
F1—C2—C3116.89 (10)C6'—C1'—C1120.41 (10)
F1—C2—C1119.00 (10)C2'—C1'—C1120.70 (10)
C3—C2—C1124.08 (11)C3'—C2'—C1'120.38 (11)
C2—C3—C4117.40 (11)C4'—C3'—C2'120.35 (11)
C5—C4—C3121.67 (10)C3'—C4'—C5'119.88 (11)
C5—C4—Cl1119.69 (9)C4'—C5'—C6'119.87 (11)
C3—C4—Cl1118.64 (9)C5'—C6'—C1'120.67 (11)
Selected geometric parameters (Å, º) for (2'F-PCB3) top
Cl1—C41.7417 (14)C1'—C2'1.3879 (19)
C1—C61.3922 (19)C1'—C6'1.4008 (19)
C1—C21.3981 (19)C2'—F11.3613 (15)
C1—C1'1.4850 (18)C2'—C3'1.3750 (19)
C2—C31.3881 (18)C3'—C4'1.387 (2)
C3—C41.382 (2)C4'—C5'1.383 (2)
C4—C51.379 (2)C5'—C6'1.3855 (19)
C5—C61.3861 (19)
C6—C1—C2118.23 (12)C2'—C1'—C6'115.68 (12)
C6—C1—C1'120.16 (11)C2'—C1'—C1122.94 (12)
C2—C1—C1'121.59 (12)C6'—C1'—C1121.37 (12)
C3—C2—C1121.05 (13)F1—C2'—C3'117.55 (12)
C4—C3—C2118.99 (13)F1—C2'—C1'118.29 (11)
C5—C4—C3121.38 (12)C3'—C2'—C1'124.15 (13)
C5—C4—Cl1119.09 (11)C2'—C3'—C4'118.55 (13)
C3—C4—Cl1119.53 (11)C5'—C4'—C3'119.68 (13)
C4—C5—C6119.11 (13)C4'—C5'—C6'120.35 (13)
C5—C6—C1121.24 (13)C5'—C6'—C1'121.58 (13)
Selected geometric parameters (Å, º) for (3'F-PCB3) top
Cl1—C41.7447 (19)C1'—C6'1.397 (3)
C1—C21.388 (3)C1'—C2'1.398 (3)
C1—C61.403 (3)C2'—C3'1.379 (3)
C1—C1'1.485 (3)C3'—C4'1.361 (4)
C2—C31.385 (3)C3'—F11.374 (3)
C3—C41.382 (3)C4'—C5'1.388 (4)
C4—C51.380 (3)C5'—C6'1.377 (3)
C5—C61.380 (3)
C2—C1—C6117.64 (17)C6'—C1'—C2'117.85 (18)
C2—C1—C1'121.83 (16)C6'—C1'—C1121.60 (19)
C6—C1—C1'120.52 (16)C2'—C1'—C1120.55 (18)
C3—C2—C1121.67 (17)C3'—C2'—C1'118.6 (2)
C4—C3—C2119.08 (18)C4'—C3'—F1118.4 (2)
C5—C4—C3120.88 (18)C4'—C3'—C2'124.2 (2)
C5—C4—Cl1119.57 (15)F1—C3'—C2'117.4 (2)
C3—C4—Cl1119.55 (15)C3'—C4'—C5'117.3 (2)
C6—C5—C4119.40 (17)C6'—C5'—C4'120.5 (2)
C5—C6—C1121.32 (17)C5'—C6'—C1'121.6 (2)
Selected geometric parameters (Å, º) for (4'F-PCB3) top
Cl1—C41.765 (2)Cl2—C4A1.744 (3)
F1—C4'1.360 (3)F2—C4'A1.395 (3)
C1—C21.397 (3)C1A—C6A1.392 (3)
C1—C61.398 (3)C1A—C2A1.401 (3)
C1—C1'1.479 (3)C1A—C1'A1.475 (3)
C2—C31.387 (3)C2A—C3A1.377 (3)
C3—C41.375 (3)C3A—C4A1.386 (4)
C4—C51.372 (3)C4A—C5A1.374 (3)
C5—C61.385 (3)C5A—C6A1.383 (3)
C1'—C2'1.394 (3)C1'A—C2'A1.397 (3)
C1'—C6'1.395 (3)C1'A—C6'A1.403 (3)
C2'—C3'1.383 (3)C2'A—C3'A1.381 (3)
C3'—C4'1.366 (4)C3'A—C4'A1.371 (3)
C4'—C5'1.378 (4)C4'A—C5'A1.374 (3)
C5'—C6'1.379 (3)C5'A—C6'A1.375 (3)
C2—C1—C6117.7 (2)C6A—C1A—C2A117.8 (2)
C2—C1—C1'121.6 (2)C6A—C1A—C1'A120.7 (2)
C6—C1—C1'120.7 (2)C2A—C1A—C1'A121.5 (2)
C3—C2—C1121.3 (2)C3A—C2A—C1A121.3 (2)
C4—C3—C2119.2 (2)C2A—C3A—C4A119.1 (2)
C5—C4—C3121.1 (2)C5A—C4A—C3A121.2 (2)
C5—C4—Cl1119.34 (19)C5A—C4A—Cl2119.7 (2)
C3—C4—Cl1119.57 (18)C3A—C4A—Cl2119.1 (2)
C4—C5—C6119.7 (2)C4A—C5A—C6A119.2 (2)
C5—C6—C1120.9 (2)C5A—C6A—C1A121.4 (2)
C2'—C1'—C6'118.0 (2)C2'A—C1'A—C6'A117.5 (2)
C2'—C1'—C1121.1 (2)C2'A—C1'A—C1A121.2 (2)
C6'—C1'—C1120.8 (2)C6'A—C1'A—C1A121.4 (2)
C3'—C2'—C1'121.1 (2)C3'A—C2'A—C1'A121.4 (2)
C4'—C3'—C2'118.7 (2)C4'A—C3'A—C2'A118.7 (2)
F1—C4'—C3'119.2 (2)C3'A—C4'A—C5'A122.3 (2)
F1—C4'—C5'118.4 (2)C3'A—C4'A—F2121.0 (2)
C3'—C4'—C5'122.4 (2)C5'A—C4'A—F2116.7 (2)
C4'—C5'—C6'118.4 (2)C4'A—C5'A—C6'A118.5 (2)
C5'—C6'—C1'121.4 (2)C5'A—C6'A—C1'A121.6 (2)
 

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