Effects of fluoro substitution on 4-bromodiphenyl ether (PBDE 3)

It is our hypothesis that fluoro substitution provides a powerful tool to modulate the desired characteristics and to increase the specificity of studies of structure–activity relationships. 4-Bromodiphenyl ether (PBDE 3) and its five corresponding monofluorinated analogues (F-PBDEs 3) have been synthesized and fully characterized (using ¹H, ¹³C and ¹⁹F NMR spectroscopy, and mass spectrometry). The accurate structure from X-ray crystal analysis was compared with iterative calculations using semi-empirical self-consistent field molecular-orbital (SCF-MO) models. The compounds studied were 4-bromodiphenyl ether (PBDE 3), the ¹³C₆-isotopically labeled PBDE 3 (¹³C₆-PBDE 3) and 2-fluoro-4-bromodiphenyl ether (3-2F), 2′-fluoro-4-bromodiphenyl ether (3-2′F), 3-fluoro-4-bromodiphenyl ether (3-3F), 3′-fluoro-4-bromodiphenyl ether (3-3′F), and 4′-fluoro-4-bromodiphenyl ether (3-4′F). Solid-state intermolecular interactions for PBDE 3 and the F-PBDEs 3 isomers are dominated by weak C—H(F,Br)...π and C—H...F interactions. The C—F bond lengths varied between 1.347 (2) and 1.362 (2) Å, and the C4—Br bond length between 1.880 (3) and 1.904 (2) Å. These bond lengths are correlated with electron-density differences, as determined by ¹³C shifts, but not with the strength of the C—F couplings. The interior ring angles of ipso-fluoro substitution increased (121.9–124.0°) as a result of hyperconjugation, a phenomenon also predicted by the calculation models. An attraction between the vicinal fluoro and halo substituents (observed in fluoro substituted chlorobiphenyls) was not observed for the bromo substituted F-PBDEs. The influence of a fluoro substituent on the conformation was only observable in PBDEs with di-ortho substitution. Calculated and observed torsion angles showed a positive correlation with increasing van der Waals radii and/or the degree of substitution for mono- to tetra-fluoro, chloro, bromo and methyl substitutions in the ortho positions of diphenyl ether. These findings utilizing F-tagged analogues presented here may prove fundamental to the interpretation of the biological effects and toxicities of these persistent environmental pollutants.

Computing details

For all compounds, data collection: Collect (Nonius BV, 1997-2000). Cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997) for BDE3, BDE3-3F, BDE3-2F, BDE3-2primeF, BDE3-4primeF; HKL SCALEPACK (Otwinowski & Minor,1997) for BDE3-3primeF. Data reduction: HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997) for BDE3, BDE3-3F, BDE3-2primeF, BDE3-4primeF; HKL DENZO, SCALEPACK (Otwinowski & Minor, 1997 for BDE3-2F; HKL DENZO, SCALEPACK (Otwinowski & Minor,1997) for BDE3-3primeF. For all compounds, program(s) used to solve structure: SHELXTL v6.1 (Sheldrick, 1997); program(s) used to refine structure: SHELXTL v6.1 (Sheldrick, 1997); molecular graphics: SHELXTL v6.1 (Sheldrick, 1997); software used to prepare material for publication: SHELXTL v6.1 (Sheldrick, 1997).

Figures

(BDE3)

Crystal data

C12H9BrO	F(000) = 496
Mr = 249.10	Dx = 1.614 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2244 reflections
a = 23.628 (3) Å	θ = 1.0–27.5°
b = 7.5461 (9) Å	µ = 3.97 mm^−1
c = 5.8066 (7) Å	T = 150 K
β = 97.919 (5)°	Plate, colorless
V = 1025.4 (2) Å^3	0.36 × 0.24 × 0.07 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2310 independent reflections
Radiation source: fine-focus sealed tube	2216 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 9 pixels mm^-1	θmax = 27.4°, θmin = 2.8°
CCD phi and ω scans	h = −30→30
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −9→9
Tmin = 0.329, Tmax = 0.769	l = −7→7
11708 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0391P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2310 reflections	Δρmax = 0.28 e Å^−3
127 parameters	Δρmin = −0.37 e Å^−3
2 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (8)

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
C1	0.32889 (10)	0.7587 (3)	0.4212 (4)	0.0263 (4)
C2	0.27897 (12)	0.8309 (4)	0.2987 (4)	0.0305 (5)
H2	0.2805	0.8909	0.1559	0.037*
C3	0.22772 (11)	0.8151 (3)	0.3845 (4)	0.0325 (5)
H3	0.1938	0.8629	0.3006	0.039*
C4	0.22599 (11)	0.7286 (3)	0.5946 (4)	0.0303 (5)
Br1	0.156020 (8)	0.70659 (3)	0.717490 (10)	0.04432 (9)
C5	0.27552 (11)	0.6593 (3)	0.7202 (4)	0.0299 (4)
H5	0.2740	0.6026	0.8653	0.036*
C6	0.32703 (11)	0.6732 (3)	0.6332 (4)	0.0292 (5)
H6	0.3609	0.6249	0.7172	0.035*
O1	0.37661 (8)	0.7681 (3)	0.3102 (3)	0.0331 (4)
C1'	0.43103 (10)	0.7572 (3)	0.4336 (4)	0.0276 (4)
C2'	0.47106 (11)	0.6654 (3)	0.3267 (4)	0.0328 (5)
H2'	0.4599	0.6053	0.1840	0.039*
C3'	0.52780 (11)	0.6620 (3)	0.4302 (5)	0.0372 (5)
H3'	0.5553	0.5990	0.3577	0.045*
C4'	0.54453 (13)	0.7504 (4)	0.6395 (5)	0.0367 (5)
H4'	0.5834	0.7493	0.7090	0.044*
C5'	0.50363 (11)	0.8399 (3)	0.7450 (4)	0.0353 (5)
H5'	0.5147	0.8986	0.8890	0.042*
C6'	0.44687 (11)	0.8453 (3)	0.6440 (4)	0.0312 (4)
H6'	0.4193	0.9079	0.7168	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0284 (11)	0.0277 (9)	0.0236 (10)	−0.0028 (8)	0.0065 (8)	−0.0024 (8)
C2	0.0377 (14)	0.0326 (10)	0.0205 (10)	0.0004 (10)	0.0015 (9)	0.0014 (9)
C3	0.0318 (12)	0.0372 (12)	0.0280 (11)	0.0026 (9)	0.0022 (9)	−0.0015 (8)
C4	0.0325 (13)	0.0344 (11)	0.0251 (10)	0.0007 (9)	0.0081 (9)	−0.0038 (8)
Br1	0.03262 (13)	0.06288 (16)	0.03977 (13)	−0.00028 (14)	0.01317 (8)	−0.00277 (15)
C5	0.0374 (13)	0.0301 (10)	0.0226 (10)	0.0008 (9)	0.0051 (9)	0.0007 (8)
C6	0.0322 (12)	0.0317 (10)	0.0234 (10)	0.0018 (8)	0.0032 (8)	0.0012 (8)
O1	0.0314 (10)	0.0464 (10)	0.0222 (8)	−0.0027 (7)	0.0064 (7)	0.0010 (7)
C1'	0.0301 (12)	0.0281 (10)	0.0257 (11)	−0.0033 (8)	0.0081 (9)	0.0021 (8)
C2'	0.0377 (13)	0.0342 (10)	0.0297 (11)	−0.0065 (10)	0.0156 (10)	−0.0035 (9)
C3'	0.0348 (13)	0.0354 (11)	0.0450 (14)	−0.0019 (10)	0.0188 (11)	−0.0012 (10)
C4'	0.0331 (14)	0.0370 (12)	0.0399 (14)	0.0004 (11)	0.0049 (11)	0.0052 (12)
C5'	0.0385 (13)	0.0373 (11)	0.0303 (11)	−0.0038 (10)	0.0052 (10)	−0.0033 (9)
C6'	0.0364 (13)	0.0295 (10)	0.0294 (11)	0.0007 (10)	0.0100 (9)	−0.0054 (9)

Geometric parameters (Å, º)

C1—O1	1.376 (3)	O1—C1'	1.386 (3)
C1—C6	1.396 (3)	C1'—C2'	1.386 (4)
C1—C2	1.401 (4)	C1'—C6'	1.396 (3)
C2—C3	1.377 (4)	C2'—C3'	1.392 (4)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.389 (3)	C3'—C4'	1.395 (4)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.393 (4)	C4'—C5'	1.389 (4)
C4—Br1	1.896 (3)	C4'—H4'	0.9500
C5—C6	1.385 (4)	C5'—C6'	1.388 (4)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
O1—C1—C6	124.4 (2)	O1—C1'—C2'	116.1 (2)
O1—C1—C2	115.4 (2)	O1—C1'—C6'	122.8 (2)
C6—C1—C2	120.1 (2)	C2'—C1'—C6'	120.8 (2)
C3—C2—C1	120.2 (2)	C1'—C2'—C3'	119.5 (2)
C3—C2—H2	119.9	C1'—C2'—H2'	120.3
C1—C2—H2	119.9	C3'—C2'—H2'	120.3
C2—C3—C4	119.5 (2)	C2'—C3'—C4'	120.5 (2)
C2—C3—H3	120.2	C2'—C3'—H3'	119.7
C4—C3—H3	120.2	C4'—C3'—H3'	119.7
C3—C4—C5	120.8 (2)	C5'—C4'—C3'	119.1 (3)
C3—C4—Br1	120.3 (2)	C5'—C4'—H4'	120.5
C5—C4—Br1	118.90 (18)	C3'—C4'—H4'	120.5
C6—C5—C4	119.9 (2)	C6'—C5'—C4'	121.2 (2)
C6—C5—H5	120.1	C6'—C5'—H5'	119.4
C4—C5—H5	120.1	C4'—C5'—H5'	119.4
C5—C6—C1	119.5 (2)	C5'—C6'—C1'	118.9 (2)
C5—C6—H6	120.2	C5'—C6'—H6'	120.6
C1—C6—H6	120.2	C1'—C6'—H6'	120.6
C1—O1—C1'	121.09 (18)
O1—C1—C2—C3	174.4 (2)	C2—C1—O1—C1'	158.7 (2)
C6—C1—C2—C3	−1.2 (4)	C1—O1—C1'—C2'	142.6 (2)
C1—C2—C3—C4	0.7 (4)	C1—O1—C1'—C6'	−42.9 (3)
C2—C3—C4—C5	0.5 (3)	O1—C1'—C2'—C3'	174.3 (2)
C2—C3—C4—Br1	179.56 (19)	C6'—C1'—C2'—C3'	−0.3 (3)
C3—C4—C5—C6	−1.3 (3)	C1'—C2'—C3'—C4'	−0.2 (4)
Br1—C4—C5—C6	179.70 (18)	C2'—C3'—C4'—C5'	0.9 (4)
C4—C5—C6—C1	0.8 (3)	C3'—C4'—C5'—C6'	−1.1 (4)
O1—C1—C6—C5	−174.7 (2)	C4'—C5'—C6'—C1'	0.6 (4)
C2—C1—C6—C5	0.4 (4)	O1—C1'—C6'—C5'	−174.2 (2)
C6—C1—O1—C1'	−25.9 (3)	C2'—C1'—C6'—C5'	0.1 (4)

(BDE3-3F)

Crystal data

C12H8BrFO	F(000) = 528
Mr = 267.09	Dx = 1.733 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4369 reflections
a = 14.9203 (16) Å	θ = 1.0–27.5°
b = 11.6841 (13) Å	µ = 4.00 mm^−1
c = 5.8727 (7) Å	T = 150 K
V = 1023.8 (2) Å^3	Plate, colorless
Z = 4	0.45 × 0.44 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2327 independent reflections
Radiation source: fine-focus sealed tube	2190 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 9 pixels mm^-1	θmax = 27.4°, θmin = 2.7°
CCD phi and ω scans	h = −18→19
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −15→15
Tmin = 0.267, Tmax = 0.741	l = −7→7
15796 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 0.1087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
2327 reflections	Δρmax = 0.44 e Å^−3
136 parameters	Δρmin = −0.32 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.021 (11)

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
C1	0.10725 (17)	0.5982 (2)	0.1522 (4)	0.0272 (6)
C2	0.07858 (15)	0.4900 (2)	0.0850 (5)	0.0254 (5)
H2	0.0478	0.4797	−0.0551	0.030*
C3	0.09566 (16)	0.3980 (2)	0.2252 (4)	0.0246 (5)
F1	0.06619 (12)	0.29363 (12)	0.1570 (3)	0.0335 (4)
C4	0.13905 (17)	0.4085 (2)	0.4306 (4)	0.0254 (5)
Br1	0.161542 (15)	0.27961 (2)	0.61370 (9)	0.03417 (10)
C5	0.16715 (15)	0.5175 (3)	0.4970 (5)	0.0273 (6)
H5	0.1979	0.5270	0.6373	0.033*
C6	0.15084 (16)	0.6114 (2)	0.3617 (5)	0.0269 (5)
H6	0.1692	0.6853	0.4106	0.032*
O1	0.09015 (15)	0.68258 (18)	−0.0024 (4)	0.0382 (5)
C1'	0.10519 (19)	0.7985 (2)	0.0522 (5)	0.0288 (6)
C2'	0.15432 (18)	0.8599 (3)	−0.1033 (5)	0.0348 (6)
H2'	0.1801	0.8233	−0.2321	0.042*
C3'	0.16563 (17)	0.9771 (3)	−0.0680 (6)	0.0385 (7)
H3'	0.1985	1.0214	−0.1749	0.046*
C4'	0.12920 (16)	1.0289 (2)	0.1218 (8)	0.0369 (5)
H4'	0.1381	1.1083	0.1470	0.044*
C5'	0.07970 (18)	0.9652 (3)	0.2752 (5)	0.0331 (6)
H5'	0.0545	1.0013	0.4052	0.040*
C6'	0.06663 (18)	0.8491 (2)	0.2405 (5)	0.0314 (6)
H6'	0.0318	0.8053	0.3443	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0328 (11)	0.0269 (11)	0.0219 (15)	0.0021 (9)	−0.0005 (10)	−0.0013 (10)
C2	0.0296 (11)	0.0303 (12)	0.0162 (14)	0.0035 (9)	−0.0012 (9)	−0.0050 (10)
C3	0.0278 (12)	0.0207 (12)	0.0253 (12)	0.0016 (9)	0.0013 (10)	−0.0056 (9)
F1	0.0457 (9)	0.0243 (7)	0.0305 (12)	−0.0003 (6)	−0.0060 (7)	−0.0056 (6)
C4	0.0261 (11)	0.0284 (13)	0.0217 (12)	0.0042 (10)	0.0015 (10)	0.0011 (10)
Br1	0.04194 (16)	0.03409 (15)	0.02648 (14)	0.00229 (9)	−0.00161 (17)	0.00695 (13)
C5	0.0285 (13)	0.0359 (14)	0.0175 (13)	−0.0023 (10)	0.0006 (9)	−0.0039 (11)
C6	0.0308 (13)	0.0270 (13)	0.0230 (13)	−0.0031 (10)	−0.0012 (10)	−0.0036 (10)
O1	0.0661 (14)	0.0249 (10)	0.0236 (10)	−0.0008 (10)	−0.0094 (10)	−0.0022 (8)
C1'	0.0361 (13)	0.0266 (12)	0.0236 (14)	0.0031 (10)	−0.0038 (10)	−0.0008 (9)
C2'	0.0402 (15)	0.0375 (15)	0.0268 (14)	0.0091 (12)	0.0052 (11)	0.0033 (12)
C3'	0.0352 (14)	0.0363 (16)	0.0439 (18)	0.0007 (11)	0.0014 (12)	0.0122 (14)
C4'	0.0313 (11)	0.0259 (11)	0.0534 (15)	0.0012 (10)	−0.0075 (17)	−0.0029 (17)
C5'	0.0311 (13)	0.0356 (14)	0.0327 (15)	0.0083 (11)	−0.0004 (11)	−0.0092 (12)
C6'	0.0295 (12)	0.0346 (15)	0.0300 (14)	−0.0012 (11)	0.0055 (11)	−0.0009 (11)

Geometric parameters (Å, º)

C1—O1	1.364 (3)	O1—C1'	1.410 (3)
C1—C2	1.392 (3)	C1'—C2'	1.373 (4)
C1—C6	1.400 (4)	C1'—C6'	1.380 (4)
C2—C3	1.377 (4)	C2'—C3'	1.396 (5)
C2—H2	0.9500	C2'—H2'	0.9500
C3—F1	1.357 (3)	C3'—C4'	1.379 (5)
C3—C4	1.374 (4)	C3'—H3'	0.9500
C4—C5	1.397 (4)	C4'—C5'	1.382 (5)
C4—Br1	1.880 (3)	C4'—H4'	0.9500
C5—C6	1.376 (4)	C5'—C6'	1.385 (4)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
O1—C1—C2	114.2 (2)	C2'—C1'—C6'	122.1 (3)
O1—C1—C6	126.3 (2)	C2'—C1'—O1	115.8 (3)
C2—C1—C6	119.5 (2)	C6'—C1'—O1	121.8 (3)
C3—C2—C1	118.8 (2)	C1'—C2'—C3'	118.6 (3)
C3—C2—H2	120.6	C1'—C2'—H2'	120.7
C1—C2—H2	120.6	C3'—C2'—H2'	120.7
F1—C3—C4	119.4 (2)	C4'—C3'—C2'	120.2 (3)
F1—C3—C2	117.7 (2)	C4'—C3'—H3'	119.9
C4—C3—C2	122.9 (2)	C2'—C3'—H3'	119.9
C3—C4—C5	117.9 (2)	C3'—C4'—C5'	120.1 (2)
C3—C4—Br1	121.0 (2)	C3'—C4'—H4'	120.0
C5—C4—Br1	121.1 (2)	C5'—C4'—H4'	120.0
C6—C5—C4	120.9 (2)	C4'—C5'—C6'	120.4 (3)
C6—C5—H5	119.6	C4'—C5'—H5'	119.8
C4—C5—H5	119.6	C6'—C5'—H5'	119.8
C5—C6—C1	120.1 (2)	C1'—C6'—C5'	118.6 (3)
C5—C6—H6	120.0	C1'—C6'—H6'	120.7
C1—C6—H6	120.0	C5'—C6'—H6'	120.7
C1—O1—C1'	120.9 (2)
O1—C1—C2—C3	177.6 (2)	C2—C1—O1—C1'	172.2 (2)
C6—C1—C2—C3	−1.3 (4)	C6—C1—O1—C1'	−8.9 (4)
C1—C2—C3—F1	179.3 (2)	C1—O1—C1'—C2'	130.0 (3)
C1—C2—C3—C4	0.7 (4)	C1—O1—C1'—C6'	−55.2 (4)
F1—C3—C4—C5	−179.0 (2)	C6'—C1'—C2'—C3'	0.3 (4)
C2—C3—C4—C5	−0.4 (4)	O1—C1'—C2'—C3'	175.1 (3)
F1—C3—C4—Br1	2.1 (3)	C1'—C2'—C3'—C4'	1.1 (4)
C2—C3—C4—Br1	−179.40 (19)	C2'—C3'—C4'—C5'	−1.4 (4)
C3—C4—C5—C6	0.7 (4)	C3'—C4'—C5'—C6'	0.3 (4)
Br1—C4—C5—C6	179.71 (19)	C2'—C1'—C6'—C5'	−1.3 (4)
C4—C5—C6—C1	−1.4 (4)	O1—C1'—C6'—C5'	−175.8 (3)
O1—C1—C6—C5	−177.1 (3)	C4'—C5'—C6'—C1'	1.0 (4)
C2—C1—C6—C5	1.7 (4)

(BDE3-2F)

Crystal data

C12H8BrFO	F(000) = 528
Mr = 267.09	Dx = 1.713 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4553 reflections
a = 5.8708 (7) Å	θ = 1.0–27.5°
b = 9.0974 (10) Å	µ = 3.95 mm^−1
c = 19.396 (2) Å	T = 150 K
V = 1035.9 (2) Å^3	Irregular prism, colorless
Z = 4	0.34 × 0.31 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	2293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.5°
CCD phi and ω scans	h = −7→7
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.315, Tmax = 0.473	l = −25→24
21969 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.016	H-atom parameters constrained
wR(F^2) = 0.038	w = 1/[σ^2(Fo^2) + (0.0168P)^2 + 0.2751P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
2373 reflections	Δρmax = 0.17 e Å^−3
170 parameters	Δρmin = −0.20 e Å^−3
46 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.003 (7)

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 stage difference fourier maps suggested disorder in the flouro- substituent. Disorder refinement confirmed this as disorder via twofold rotation about the C1—C4 direction. The disorder was modeled as whole molecule disorder with the conformations constrained to be the same and partial atoms in close proximity (<0.5 A) were constrained to have the same thermal parameters (e.g. Uaniso(C1)=Uaniso(C1"), Uaniso(c2)=Uaniso(C6"), etc.). F1" was assigned U_iso(F2")=1.2*U_iso,eq(C2"). The relative occupancies refined to 0.932 (2) for the major site and 0.068 (2) for the minor site (labels with " appended).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5609 (3)	0.63774 (17)	0.88987 (8)	0.0283 (4)	0.932 (2)
C2	0.7540 (3)	0.69569 (19)	0.91977 (7)	0.0295 (4)	0.932 (2)
F1	0.8040 (2)	0.65919 (14)	0.98544 (5)	0.0443 (3)	0.932 (2)
C3	0.8997 (3)	0.78760 (18)	0.88401 (8)	0.0284 (4)	0.932 (2)
H3	1.0321	0.8270	0.9052	0.034*	0.932 (2)
C4	0.8461 (3)	0.82021 (18)	0.81628 (9)	0.0247 (3)	0.932 (2)
Br1	1.04090 (7)	0.94633 (5)	0.76543 (3)	0.03277 (7)	0.932 (2)
C5	0.6538 (3)	0.76432 (19)	0.78458 (10)	0.0294 (4)	0.932 (2)
H5	0.6203	0.7881	0.7380	0.035*	0.932 (2)
C6	0.5102 (3)	0.6726 (2)	0.82206 (10)	0.0321 (4)	0.932 (2)
H6	0.3769	0.6338	0.8011	0.038*	0.932 (2)
O1	0.4158 (2)	0.54952 (15)	0.92844 (8)	0.0368 (3)	0.932 (2)
C1'	0.4321 (5)	0.39811 (18)	0.91652 (13)	0.0259 (4)	0.932 (2)
C2'	0.2461 (6)	0.3150 (3)	0.9368 (3)	0.0288 (4)	0.932 (2)
H2'	0.1156	0.3607	0.9563	0.035*	0.932 (2)
C3'	0.2540 (8)	0.1634 (3)	0.9282 (5)	0.0325 (4)	0.932 (2)
H3'	0.1284	0.1048	0.9423	0.039*	0.932 (2)
C4'	0.4444 (9)	0.0970 (3)	0.8992 (5)	0.0326 (4)	0.932 (2)
H4'	0.4485	−0.0065	0.8931	0.039*	0.932 (2)
C5'	0.6269 (9)	0.1820 (3)	0.8794 (5)	0.0298 (4)	0.932 (2)
H5'	0.7573	0.1364	0.8599	0.036*	0.932 (2)
C6'	0.6226 (7)	0.3343 (2)	0.8878 (3)	0.0271 (6)	0.932 (2)
H6'	0.7486	0.3928	0.8740	0.033*	0.932 (2)
C1"	0.5906 (7)	0.6327 (2)	0.8993 (3)	0.0283 (4)	0.068 (2)
C2"	0.5392 (7)	0.6631 (2)	0.8315 (3)	0.0321 (4)	0.068 (2)
F1"	0.3491 (7)	0.6043 (2)	0.8038 (3)	0.038*	0.068 (2)
C3"	0.6763 (7)	0.7518 (2)	0.7912 (3)	0.0294 (4)	0.068 (2)
H3"	0.6389	0.7719	0.7445	0.035*	0.068 (2)
C4"	0.8699 (9)	0.8103 (6)	0.8211 (4)	0.0247 (3)	0.068 (2)
Br1"	1.0632 (9)	0.9322 (6)	0.7676 (4)	0.03277 (7)	0.068 (2)
C5"	0.9271 (10)	0.7824 (6)	0.8890 (4)	0.0284 (4)	0.068 (2)
H5"	1.0608	0.8238	0.9086	0.034*	0.068 (2)
C6"	0.7854 (10)	0.6926 (6)	0.9282 (4)	0.0295 (4)	0.068 (2)
H6"	0.8225	0.6724	0.9749	0.035*	0.068 (2)
O1"	0.4476 (10)	0.5431 (6)	0.9379 (4)	0.0368 (3)	0.068 (2)
C1'"	0.448 (5)	0.3938 (9)	0.9202 (16)	0.0259 (4)	0.068 (2)
C2'"	0.254 (7)	0.316 (3)	0.938 (4)	0.0288 (4)	0.068 (2)
H2'"	0.1272	0.3641	0.9584	0.035*	0.068 (2)
C3'"	0.250 (10)	0.165 (3)	0.927 (6)	0.0325 (4)	0.068 (2)
H3'"	0.1188	0.1097	0.9392	0.039*	0.068 (2)
C4'"	0.437 (11)	0.094 (2)	0.898 (7)	0.0326 (4)	0.068 (2)
H4'"	0.4328	−0.0089	0.8902	0.039*	0.068 (2)
C5'"	0.627 (12)	0.174 (3)	0.880 (7)	0.0298 (4)	0.068 (2)
H5'"	0.7540	0.1259	0.8603	0.036*	0.068 (2)
C6'"	0.634 (9)	0.326 (2)	0.891 (5)	0.0271 (6)	0.068 (2)
H6'"	0.7658	0.3809	0.8791	0.033*	0.068 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0304 (8)	0.0199 (7)	0.0348 (9)	0.0015 (7)	0.0074 (8)	−0.0022 (6)
C2	0.0369 (9)	0.0268 (9)	0.0247 (9)	0.0044 (7)	0.0006 (8)	0.0014 (7)
F1	0.0565 (8)	0.0474 (7)	0.0291 (6)	−0.0074 (6)	−0.0023 (5)	0.0088 (5)
C3	0.0300 (9)	0.0283 (8)	0.0268 (8)	−0.0005 (7)	−0.0041 (7)	−0.0013 (6)
C4	0.0268 (8)	0.0200 (7)	0.0274 (8)	0.0027 (6)	0.0029 (7)	−0.0010 (6)
Br1	0.03409 (12)	0.03348 (12)	0.03075 (10)	−0.00160 (10)	0.00632 (10)	0.00341 (10)
C5	0.0333 (9)	0.0283 (8)	0.0266 (9)	0.0031 (7)	−0.0061 (7)	−0.0022 (6)
C6	0.0294 (10)	0.0285 (8)	0.0384 (9)	−0.0015 (7)	−0.0039 (7)	−0.0070 (7)
O1	0.0399 (7)	0.0243 (6)	0.0461 (8)	−0.0029 (6)	0.0194 (6)	−0.0052 (6)
C1'	0.0295 (9)	0.0250 (7)	0.0230 (8)	−0.0003 (7)	0.0019 (7)	0.0002 (6)
C2'	0.0252 (8)	0.0334 (9)	0.0279 (9)	0.0004 (7)	0.0028 (8)	−0.0010 (7)
C3'	0.0335 (9)	0.0335 (9)	0.0305 (10)	−0.0090 (8)	0.0000 (8)	0.0010 (7)
C4'	0.0402 (10)	0.0264 (8)	0.0313 (10)	−0.0012 (8)	−0.0067 (10)	−0.0012 (7)
C5'	0.0320 (8)	0.0285 (9)	0.0290 (9)	0.0051 (8)	0.0022 (7)	−0.0004 (10)
C6'	0.0250 (9)	0.0297 (8)	0.0266 (12)	−0.0022 (7)	0.0016 (9)	0.0009 (9)
C1"	0.0304 (8)	0.0199 (7)	0.0348 (9)	0.0015 (7)	0.0074 (8)	−0.0022 (6)
C2"	0.0294 (10)	0.0285 (8)	0.0384 (9)	−0.0015 (7)	−0.0039 (7)	−0.0070 (7)
C3"	0.0333 (9)	0.0283 (8)	0.0266 (9)	0.0031 (7)	−0.0061 (7)	−0.0022 (6)
C4"	0.0268 (8)	0.0200 (7)	0.0274 (8)	0.0027 (6)	0.0029 (7)	−0.0010 (6)
Br1"	0.03409 (12)	0.03348 (12)	0.03075 (10)	−0.00160 (10)	0.00632 (10)	0.00341 (10)
C5"	0.0300 (9)	0.0283 (8)	0.0268 (8)	−0.0005 (7)	−0.0041 (7)	−0.0013 (6)
C6"	0.0369 (9)	0.0268 (9)	0.0247 (9)	0.0044 (7)	0.0006 (8)	0.0014 (7)
O1"	0.0399 (7)	0.0243 (6)	0.0461 (8)	−0.0029 (6)	0.0194 (6)	−0.0052 (6)
C1'"	0.0295 (9)	0.0250 (7)	0.0230 (8)	−0.0003 (7)	0.0019 (7)	0.0002 (6)
C2'"	0.0252 (8)	0.0334 (9)	0.0279 (9)	0.0004 (7)	0.0028 (8)	−0.0010 (7)
C3'"	0.0335 (9)	0.0335 (9)	0.0305 (10)	−0.0090 (8)	0.0000 (8)	0.0010 (7)
C4'"	0.0402 (10)	0.0264 (8)	0.0313 (10)	−0.0012 (8)	−0.0067 (10)	−0.0012 (7)
C5'"	0.0320 (8)	0.0285 (9)	0.0290 (9)	0.0051 (8)	0.0022 (7)	−0.0004 (10)
C6'"	0.0250 (9)	0.0297 (8)	0.0266 (12)	−0.0022 (7)	0.0016 (9)	0.0009 (9)

Geometric parameters (Å, º)

C1—C2	1.3782 (14)	C1"—C2"	1.3780
C1—O1	1.3889 (18)	C1"—O1"	1.389 (2)
C1—C6	1.385 (2)	C1"—C6"	1.385 (3)
C2—F1	1.3488 (13)	C2"—F1"	1.3488
C2—C3	1.3827 (14)	C2"—C3"	1.3826
C3—C4	1.383 (2)	C3"—C4"	1.383 (3)
C3—H3	0.9500	C3"—H3"	0.9500
C4—C5	1.382 (3)	C4"—C5"	1.382 (3)
C4—Br1	1.8965 (17)	C4"—Br1"	1.897 (2)
C5—C6	1.391 (3)	C5"—C6"	1.391 (3)
C5—H5	0.9500	C5"—H5"	0.9500
C6—H6	0.9500	C6"—H6"	0.9500
O1—C1'	1.400 (2)	O1"—C1'"	1.400 (3)
C1'—C6'	1.378 (2)	C1'"—C6'"	1.378 (3)
C1'—C2'	1.385 (2)	C1'"—C2'"	1.385 (3)
C2'—C3'	1.389 (3)	C2'"—C3'"	1.389 (3)
C2'—H2'	0.9500	C2'"—H2'"	0.9500
C3'—C4'	1.389 (3)	C3'"—C4'"	1.389 (3)
C3'—H3'	0.9500	C3'"—H3'"	0.9500
C4'—C5'	1.376 (3)	C4'"—C5'"	1.376 (3)
C4'—H4'	0.9500	C4'"—H4'"	0.9500
C5'—C6'	1.395 (2)	C5'"—C6'"	1.395 (3)
C5'—H5'	0.9500	C5'"—H5'"	0.9500
C6'—H6'	0.9500	C6'"—H6'"	0.9500
C2—C1—O1	119.93 (13)	C2"—C1"—O1"	119.9 (2)
C2—C1—C6	119.24 (13)	C2"—C1"—C6"	119.22 (15)
O1—C1—C6	120.80 (14)	O1"—C1"—C6"	120.8 (2)
F1—C2—C1	118.85 (11)	F1"—C2"—C1"	118.9
F1—C2—C3	119.19 (12)	F1"—C2"—C3"	119.2
C1—C2—C3	121.95 (10)	C1"—C2"—C3"	122.0
C4—C3—C2	117.75 (13)	C4"—C3"—C2"	117.76 (14)
C4—C3—H3	121.1	C4"—C3"—H3"	121.1
C2—C3—H3	121.1	C2"—C3"—H3"	121.1
C3—C4—C5	121.95 (16)	C3"—C4"—C5"	121.94 (19)
C3—C4—Br1	119.12 (12)	C3"—C4"—Br1"	119.11 (19)
C5—C4—Br1	118.92 (13)	C5"—C4"—Br1"	118.9 (2)
C4—C5—C6	118.88 (17)	C4"—C5"—C6"	118.9 (2)
C4—C5—H5	120.6	C4"—C5"—H5"	120.6
C6—C5—H5	120.6	C6"—C5"—H5"	120.6
C5—C6—C1	120.23 (16)	C5"—C6"—C1"	120.2 (2)
C5—C6—H6	119.9	C5"—C6"—H6"	119.9
C1—C6—H6	119.9	C1"—C6"—H6"	119.9
C1—O1—C1'	115.96 (12)	C1"—O1"—C1'"	115.9 (2)
C6'—C1'—C2'	121.65 (15)	C6'"—C1'"—C2'"	121.6 (2)
C6'—C1'—O1	122.46 (16)	C6'"—C1'"—O1"	122.4 (3)
C2'—C1'—O1	115.88 (16)	C2'"—C1'"—O1"	115.8 (3)
C1'—C2'—C3'	118.77 (16)	C1'"—C2'"—C3'"	118.8 (2)
C1'—C2'—H2'	120.6	C1'"—C2'"—H2'"	120.6
C3'—C2'—H2'	120.6	C3'"—C2'"—H2'"	120.6
C2'—C3'—C4'	120.46 (16)	C2'"—C3'"—C4'"	120.5 (2)
C2'—C3'—H3'	119.8	C2'"—C3'"—H3'"	119.8
C4'—C3'—H3'	119.8	C4'"—C3'"—H3'"	119.8
C5'—C4'—C3'	119.67 (15)	C5'"—C4'"—C3'"	119.7 (2)
C5'—C4'—H4'	120.2	C5'"—C4'"—H4'"	120.2
C3'—C4'—H4'	120.2	C3'"—C4'"—H4'"	120.2
C4'—C5'—C6'	120.77 (16)	C4'"—C5'"—C6'"	120.8 (2)
C4'—C5'—H5'	119.6	C4'"—C5'"—H5'"	119.6
C6'—C5'—H5'	119.6	C6'"—C5'"—H5'"	119.6
C1'—C6'—C5'	118.67 (16)	C1'"—C6'"—C5'"	118.7 (2)
C1'—C6'—H6'	120.7	C1'"—C6'"—H6'"	120.7
C5'—C6'—H6'	120.7	C5'"—C6'"—H6'"	120.7
O1—C1—C2—F1	3.3 (3)	O1"—C1"—C2"—F1"	0.0 (3)
C6—C1—C2—F1	−178.91 (16)	C6"—C1"—C2"—F1"	−180.0 (3)
O1—C1—C2—C3	−178.02 (16)	O1"—C1"—C2"—C3"	179.9 (3)
C6—C1—C2—C3	−0.2 (3)	C6"—C1"—C2"—C3"	0.0 (3)
F1—C2—C3—C4	178.57 (16)	F1"—C2"—C3"—C4"	180.0 (3)
C1—C2—C3—C4	−0.1 (3)	C1"—C2"—C3"—C4"	0.0 (3)
C2—C3—C4—C5	0.2 (3)	C2"—C3"—C4"—C5"	0.0 (7)
C2—C3—C4—Br1	179.82 (13)	C2"—C3"—C4"—Br1"	179.8 (3)
C3—C4—C5—C6	0.0 (3)	C3"—C4"—C5"—C6"	0.0 (9)
Br1—C4—C5—C6	−179.57 (13)	Br1"—C4"—C5"—C6"	−179.8 (5)
C4—C5—C6—C1	−0.4 (3)	C4"—C5"—C6"—C1"	0.0 (9)
C2—C1—C6—C5	0.4 (3)	C2"—C1"—C6"—C5"	0.0 (7)
O1—C1—C6—C5	178.26 (16)	O1"—C1"—C6"—C5"	−179.9 (5)
C2—C1—O1—C1'	−102.7 (2)	C2"—C1"—O1"—C1'"	71 (2)
C6—C1—O1—C1'	79.5 (3)	C6"—C1"—O1"—C1'"	−109 (2)
C1—O1—C1'—C6'	21.3 (4)	C1"—O1"—C1'"—C6'"	28 (5)
C1—O1—C1'—C2'	−160.1 (3)	C1"—O1"—C1'"—C2'"	−157 (4)
C6'—C1'—C2'—C3'	0.4 (3)	C6'"—C1'"—C2'"—C3'"	0.0 (3)
O1—C1'—C2'—C3'	−178.2 (4)	O1"—C1'"—C2'"—C3'"	−175 (5)
C1'—C2'—C3'—C4'	−0.6 (3)	C1'"—C2'"—C3'"—C4'"	0.0 (3)
C2'—C3'—C4'—C5'	0.5 (3)	C2'"—C3'"—C4'"—C5'"	0.0 (7)
C3'—C4'—C5'—C6'	−0.4 (3)	C3'"—C4'"—C5'"—C6'"	0.0 (9)
C2'—C1'—C6'—C5'	−0.2 (3)	C2'"—C1'"—C6'"—C5'"	0.0 (6)
O1—C1'—C6'—C5'	178.3 (4)	O1"—C1'"—C6'"—C5'"	175 (5)
C4'—C5'—C6'—C1'	0.2 (3)	C4'"—C5'"—C6'"—C1'"	0.0 (9)

(BDE3-2primeF)

Crystal data

C12H8BrFO	F(000) = 1056
Mr = 267.09	Dx = 1.715 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4514 reflections
a = 23.752 (3) Å	θ = 1.0–27.5°
b = 4.3622 (5) Å	µ = 3.95 mm^−1
c = 21.357 (3) Å	T = 150 K
β = 110.762 (5)°	Plate, colorless
V = 2069.1 (5) Å^3	0.19 × 0.16 × 0.06 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	2367 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
CCD phi and ω scans	h = −30→29
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −5→5
Tmin = 0.520, Tmax = 0.797	l = −27→27
19505 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 1.6942P] where P = (Fo^2 + 2Fc^2)/3
2367 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.46 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
C1	0.44488 (8)	0.7133 (5)	0.09014 (9)	0.0276 (4)
C2	0.38924 (9)	0.6094 (5)	0.04813 (10)	0.0328 (5)
H2	0.3866	0.4702	0.0130	0.039*
C3	0.33756 (9)	0.7085 (5)	0.05748 (10)	0.0333 (4)
H3	0.2992	0.6373	0.0290	0.040*
C4	0.34209 (9)	0.9125 (5)	0.10864 (10)	0.0299 (4)
Br1	0.271130 (9)	1.05954 (6)	0.120530 (11)	0.03931 (10)
C5	0.39742 (10)	1.0157 (5)	0.15066 (11)	0.0341 (5)
H5	0.4000	1.1545	0.1858	0.041*
C6	0.44952 (9)	0.9157 (5)	0.14131 (10)	0.0312 (4)
H6	0.4879	0.9862	0.1699	0.037*
O1	0.49374 (6)	0.6021 (4)	0.07605 (7)	0.0344 (3)
C1'	0.55085 (8)	0.7126 (5)	0.11245 (9)	0.0301 (4)
C2'	0.58143 (10)	0.6171 (5)	0.17734 (10)	0.0333 (5)
F1	0.55300 (7)	0.4306 (3)	0.20677 (7)	0.0480 (4)
C3'	0.63949 (9)	0.7086 (5)	0.21246 (11)	0.0367 (5)
H3'	0.6596	0.6413	0.2571	0.044*
C4'	0.66800 (10)	0.9005 (5)	0.18154 (12)	0.0396 (5)
H4'	0.7081	0.9662	0.2051	0.048*
C5'	0.63832 (10)	0.9973 (6)	0.11634 (13)	0.0422 (6)
H5'	0.6582	1.1276	0.0952	0.051*
C6'	0.57946 (10)	0.9040 (5)	0.08178 (11)	0.0366 (5)
H6'	0.5590	0.9719	0.0372	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0287 (9)	0.0307 (10)	0.0242 (9)	0.0018 (8)	0.0104 (7)	0.0035 (8)
C2	0.0339 (11)	0.0380 (12)	0.0228 (9)	0.0000 (8)	0.0056 (8)	−0.0049 (8)
C3	0.0266 (9)	0.0399 (12)	0.0284 (10)	−0.0009 (9)	0.0037 (8)	−0.0019 (9)
C4	0.0252 (9)	0.0356 (11)	0.0305 (10)	0.0011 (8)	0.0118 (8)	0.0024 (8)
Br1	0.02741 (13)	0.05074 (16)	0.04058 (14)	0.00186 (9)	0.01304 (10)	−0.00527 (10)
C5	0.0314 (10)	0.0381 (12)	0.0337 (11)	−0.0038 (8)	0.0125 (9)	−0.0083 (9)
C6	0.0251 (9)	0.0362 (11)	0.0311 (10)	−0.0052 (8)	0.0086 (8)	−0.0050 (9)
O1	0.0272 (7)	0.0457 (9)	0.0301 (7)	0.0000 (6)	0.0097 (6)	−0.0088 (6)
C1'	0.0270 (9)	0.0336 (11)	0.0303 (10)	0.0042 (8)	0.0109 (8)	−0.0026 (8)
C2'	0.0362 (11)	0.0317 (12)	0.0332 (10)	−0.0007 (8)	0.0139 (9)	−0.0006 (8)
F1	0.0519 (8)	0.0491 (9)	0.0376 (7)	−0.0133 (6)	0.0093 (6)	0.0101 (6)
C3'	0.0334 (11)	0.0377 (12)	0.0343 (11)	0.0039 (9)	0.0063 (9)	−0.0044 (9)
C4'	0.0279 (10)	0.0434 (14)	0.0483 (13)	0.0001 (9)	0.0144 (10)	−0.0119 (10)
C5'	0.0359 (12)	0.0476 (14)	0.0511 (14)	−0.0015 (9)	0.0251 (11)	0.0009 (11)
C6'	0.0329 (11)	0.0457 (14)	0.0345 (11)	0.0058 (9)	0.0160 (9)	0.0033 (9)

Geometric parameters (Å, º)

C1—C6	1.379 (3)	O1—C1'	1.389 (2)
C1—C2	1.384 (3)	C1'—C6'	1.380 (3)
C1—O1	1.386 (2)	C1'—C2'	1.381 (3)
C2—C3	1.381 (3)	C2'—F1	1.347 (2)
C2—H2	0.9500	C2'—C3'	1.375 (3)
C3—C4	1.383 (3)	C3'—C4'	1.383 (3)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.378 (3)	C4'—C5'	1.385 (4)
C4—Br1	1.903 (2)	C4'—H4'	0.9500
C5—C6	1.392 (3)	C5'—C6'	1.390 (3)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
C6—C1—C2	120.87 (18)	C6'—C1'—C2'	119.11 (19)
C6—C1—O1	123.96 (17)	C6'—C1'—O1	119.48 (18)
C2—C1—O1	115.16 (17)	C2'—C1'—O1	121.24 (19)
C3—C2—C1	119.80 (19)	F1—C2'—C3'	119.52 (19)
C3—C2—H2	120.1	F1—C2'—C1'	118.56 (19)
C1—C2—H2	120.1	C3'—C2'—C1'	121.9 (2)
C2—C3—C4	119.43 (18)	C2'—C3'—C4'	118.8 (2)
C2—C3—H3	120.3	C2'—C3'—H3'	120.6
C4—C3—H3	120.3	C4'—C3'—H3'	120.6
C5—C4—C3	120.92 (19)	C3'—C4'—C5'	120.2 (2)
C5—C4—Br1	119.22 (16)	C3'—C4'—H4'	119.9
C3—C4—Br1	119.85 (15)	C5'—C4'—H4'	119.9
C4—C5—C6	119.7 (2)	C4'—C5'—C6'	120.2 (2)
C4—C5—H5	120.2	C4'—C5'—H5'	119.9
C6—C5—H5	120.2	C6'—C5'—H5'	119.9
C1—C6—C5	119.29 (18)	C1'—C6'—C5'	119.8 (2)
C1—C6—H6	120.4	C1'—C6'—H6'	120.1
C5—C6—H6	120.4	C5'—C6'—H6'	120.1
C1—O1—C1'	118.93 (15)
C6—C1—C2—C3	−0.1 (3)	C1—O1—C1'—C2'	76.1 (3)
O1—C1—C2—C3	−179.43 (18)	C6'—C1'—C2'—F1	179.92 (19)
C1—C2—C3—C4	0.4 (3)	O1—C1'—C2'—F1	−4.8 (3)
C2—C3—C4—C5	−0.6 (3)	C6'—C1'—C2'—C3'	0.3 (3)
C2—C3—C4—Br1	178.29 (16)	O1—C1'—C2'—C3'	175.6 (2)
C3—C4—C5—C6	0.5 (3)	F1—C2'—C3'—C4'	−179.91 (19)
Br1—C4—C5—C6	−178.35 (16)	C1'—C2'—C3'—C4'	−0.3 (3)
C2—C1—C6—C5	0.1 (3)	C2'—C3'—C4'—C5'	−0.1 (3)
O1—C1—C6—C5	179.31 (19)	C3'—C4'—C5'—C6'	0.5 (4)
C4—C5—C6—C1	−0.3 (3)	C2'—C1'—C6'—C5'	0.1 (3)
C6—C1—O1—C1'	−4.1 (3)	O1—C1'—C6'—C5'	−175.24 (19)
C2—C1—O1—C1'	175.13 (18)	C4'—C5'—C6'—C1'	−0.5 (3)
C1—O1—C1'—C6'	−108.7 (2)

(BDE3-3primeF)

Crystal data

C12H8BrFO	F(000) = 528
Mr = 267.09	Dx = 1.694 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4604 reflections
a = 5.9477 (7) Å	θ = 1.0–27.5°
b = 9.0635 (10) Å	µ = 3.91 mm^−1
c = 19.481 (2) Å	T = 150 K
β = 94.030 (5)°	Needle, colorless
V = 1047.6 (2) Å^3	0.38 × 0.08 × 0.07 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2390 independent reflections
Radiation source: fine-focus sealed tube	1891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
CCD phi and ω scans	h = −7→7
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor,1997)	k = −11→11
Tmin = 0.318, Tmax = 0.772	l = −25→24
21638 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.3505P] where P = (Fo^2 + 2Fc^2)/3
2390 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.51 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
C1	0.6770 (4)	0.6805 (2)	0.62281 (11)	0.0284 (4)
C2	0.4858 (4)	0.7313 (2)	0.58579 (11)	0.0339 (5)
H2	0.4546	0.7022	0.5392	0.041*
C3	0.3401 (4)	0.8250 (2)	0.61713 (11)	0.0336 (5)
H3	0.2075	0.8605	0.5925	0.040*
C4	0.3905 (3)	0.8660 (2)	0.68479 (10)	0.0264 (4)
Br1	0.19567 (4)	0.99890 (2)	0.727610 (11)	0.03544 (10)
C5	0.5799 (4)	0.8145 (2)	0.72189 (11)	0.0319 (5)
H5	0.6108	0.8432	0.7685	0.038*
C6	0.7248 (4)	0.7206 (2)	0.69057 (11)	0.0322 (5)
H6	0.8561	0.6840	0.7155	0.039*
O1	0.8308 (3)	0.59279 (16)	0.59072 (8)	0.0343 (4)
C1'	0.7969 (4)	0.4418 (2)	0.58983 (10)	0.0257 (4)
C2'	0.9690 (4)	0.3600 (2)	0.56347 (10)	0.0285 (4)
H2'	1.0993	0.4063	0.5478	0.034*
C3'	0.9427 (4)	0.2091 (2)	0.56099 (11)	0.0313 (5)
F1	1.1102 (2)	0.12924 (14)	0.53441 (8)	0.0469 (4)
C4'	0.7600 (4)	0.1359 (2)	0.58360 (11)	0.0358 (5)
H4'	0.7491	0.0314	0.5813	0.043*
C5'	0.5923 (4)	0.2205 (3)	0.60989 (11)	0.0332 (5)
H5'	0.4640	0.1730	0.6262	0.040*
C6'	0.6077 (4)	0.3742 (2)	0.61292 (10)	0.0276 (4)
H6'	0.4907	0.4312	0.6305	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0305 (11)	0.0223 (10)	0.0332 (10)	0.0003 (8)	0.0086 (9)	−0.0002 (8)
C2	0.0409 (12)	0.0358 (11)	0.0246 (10)	0.0046 (10)	−0.0008 (9)	−0.0041 (9)
C3	0.0311 (11)	0.0375 (12)	0.0314 (11)	0.0053 (9)	−0.0034 (9)	−0.0001 (9)
C4	0.0291 (10)	0.0228 (9)	0.0281 (10)	−0.0016 (8)	0.0071 (8)	−0.0007 (8)
Br1	0.03496 (16)	0.03472 (15)	0.03812 (16)	0.00202 (9)	0.01294 (10)	−0.00459 (8)
C5	0.0338 (12)	0.0341 (11)	0.0273 (10)	−0.0009 (9)	−0.0022 (8)	−0.0041 (9)
C6	0.0299 (11)	0.0315 (10)	0.0344 (11)	0.0030 (9)	−0.0030 (9)	0.0004 (9)
O1	0.0339 (8)	0.0257 (7)	0.0454 (9)	−0.0014 (6)	0.0170 (7)	−0.0020 (6)
C1'	0.0307 (11)	0.0255 (10)	0.0207 (9)	−0.0003 (9)	0.0008 (8)	0.0001 (8)
C2'	0.0250 (10)	0.0327 (11)	0.0279 (10)	0.0024 (8)	0.0019 (8)	0.0011 (8)
C3'	0.0286 (11)	0.0312 (11)	0.0333 (11)	0.0083 (9)	−0.0037 (9)	−0.0041 (8)
F1	0.0375 (8)	0.0367 (7)	0.0663 (9)	0.0114 (6)	0.0035 (7)	−0.0104 (7)
C4'	0.0381 (13)	0.0261 (10)	0.0421 (12)	−0.0010 (9)	−0.0052 (10)	0.0001 (9)
C5'	0.0322 (11)	0.0341 (11)	0.0324 (11)	−0.0071 (9)	−0.0025 (9)	0.0020 (9)
C6'	0.0285 (11)	0.0321 (11)	0.0223 (9)	0.0000 (8)	0.0026 (8)	0.0007 (8)

Geometric parameters (Å, º)

C1—C6	1.379 (3)	O1—C1'	1.384 (3)
C1—C2	1.382 (3)	C1'—C6'	1.384 (3)
C1—O1	1.393 (2)	C1'—C2'	1.391 (3)
C2—C3	1.386 (3)	C2'—C3'	1.377 (3)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.382 (3)	C3'—F1	1.362 (2)
C3—H3	0.9500	C3'—C4'	1.371 (3)
C4—C5	1.376 (3)	C4'—C5'	1.385 (3)
C4—Br1	1.9041 (19)	C4'—H4'	0.9500
C5—C6	1.384 (3)	C5'—C6'	1.397 (3)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
C6—C1—C2	121.24 (19)	O1—C1'—C6'	123.73 (18)
C6—C1—O1	118.8 (2)	O1—C1'—C2'	114.91 (17)
C2—C1—O1	119.88 (18)	C6'—C1'—C2'	121.35 (19)
C1—C2—C3	119.45 (19)	C3'—C2'—C1'	117.2 (2)
C1—C2—H2	120.3	C3'—C2'—H2'	121.4
C3—C2—H2	120.3	C1'—C2'—H2'	121.4
C4—C3—C2	119.0 (2)	F1—C3'—C4'	118.82 (19)
C4—C3—H3	120.5	F1—C3'—C2'	117.15 (19)
C2—C3—H3	120.5	C4'—C3'—C2'	124.0 (2)
C5—C4—C3	121.63 (19)	C3'—C4'—C5'	117.3 (2)
C5—C4—Br1	119.01 (15)	C3'—C4'—H4'	121.4
C3—C4—Br1	119.35 (16)	C5'—C4'—H4'	121.4
C4—C5—C6	119.29 (19)	C4'—C5'—C6'	121.4 (2)
C4—C5—H5	120.4	C4'—C5'—H5'	119.3
C6—C5—H5	120.4	C6'—C5'—H5'	119.3
C1—C6—C5	119.4 (2)	C1'—C6'—C5'	118.7 (2)
C1—C6—H6	120.3	C1'—C6'—H6'	120.6
C5—C6—H6	120.3	C5'—C6'—H6'	120.6
C1'—O1—C1	118.05 (15)
C6—C1—C2—C3	0.4 (3)	C1—O1—C1'—C6'	6.6 (3)
O1—C1—C2—C3	−176.51 (19)	C1—O1—C1'—C2'	−173.55 (18)
C1—C2—C3—C4	0.3 (3)	O1—C1'—C2'—C3'	−179.55 (18)
C2—C3—C4—C5	−0.9 (3)	C6'—C1'—C2'—C3'	0.3 (3)
C2—C3—C4—Br1	178.31 (16)	C1'—C2'—C3'—F1	179.24 (17)
C3—C4—C5—C6	0.6 (3)	C1'—C2'—C3'—C4'	−0.9 (3)
Br1—C4—C5—C6	−178.54 (16)	F1—C3'—C4'—C5'	−179.58 (19)
C2—C1—C6—C5	−0.6 (3)	C2'—C3'—C4'—C5'	0.6 (3)
O1—C1—C6—C5	176.31 (18)	C3'—C4'—C5'—C6'	0.3 (3)
C4—C5—C6—C1	0.1 (3)	O1—C1'—C6'—C5'	−179.64 (18)
C6—C1—O1—C1'	94.9 (2)	C2'—C1'—C6'—C5'	0.5 (3)
C2—C1—O1—C1'	−88.1 (2)	C4'—C5'—C6'—C1'	−0.8 (3)

(BDE3-4primeF)

Crystal data

C12H8BrFO	F(000) = 528
Mr = 267.09	Dx = 1.715 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2317 reflections
a = 6.0033 (7) Å	θ = 1.0–27.5°
b = 23.186 (3) Å	µ = 3.96 mm^−1
c = 7.4329 (8) Å	T = 150 K
β = 91.480 (5)°	Plate, colorless
V = 1034.3 (2) Å^3	0.33 × 0.16 × 0.03 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2289 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.3°
CCD phi and ω scans	h = −7→7
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor, 1997)	k = −30→30
Tmin = 0.355, Tmax = 0.891	l = −9→9
9753 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.0519P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2289 reflections	Δρmax = 0.38 e Å^−3
136 parameters	Δρmin = −0.73 e Å^−3
2 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (10)

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
C1	0.4554 (5)	0.10860 (13)	0.7388 (3)	0.0319 (6)
C2	0.2550 (5)	0.11709 (13)	0.8224 (4)	0.0320 (6)
H2	0.2119	0.1547	0.8589	0.038*
C3	0.1168 (4)	0.07003 (14)	0.8526 (3)	0.0302 (5)
H3	−0.0228	0.0751	0.9079	0.036*
C4	0.1870 (4)	0.01555 (13)	0.8004 (3)	0.0285 (6)
Br1	−0.00105 (6)	−0.048949 (10)	0.83625 (6)	0.03478 (9)
C5	0.3888 (5)	0.00713 (13)	0.7213 (4)	0.0294 (5)
H5	0.4346	−0.0306	0.6884	0.035*
C6	0.5246 (5)	0.05422 (11)	0.6899 (4)	0.0298 (6)
H6	0.6644	0.0491	0.6351	0.036*
O1	0.5914 (4)	0.15666 (9)	0.7153 (3)	0.0424 (5)
C1'	0.6675 (5)	0.16771 (12)	0.5446 (4)	0.0310 (6)
C2'	0.8637 (5)	0.19853 (12)	0.5355 (4)	0.0342 (6)
H2'	0.9415	0.2095	0.6431	0.041*
C3'	0.9472 (5)	0.21347 (12)	0.3700 (4)	0.0355 (6)
H3'	1.0820	0.2347	0.3626	0.043*
C4'	0.8312 (5)	0.19692 (13)	0.2165 (4)	0.0348 (6)
F1	0.9138 (4)	0.21033 (9)	0.0540 (3)	0.0496 (5)
C5'	0.6347 (5)	0.16654 (13)	0.2224 (4)	0.0370 (6)
H5'	0.5581	0.1556	0.1143	0.044*
C6'	0.5494 (5)	0.15205 (12)	0.3892 (4)	0.0337 (6)
H6'	0.4124	0.1318	0.3964	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0385 (15)	0.0325 (15)	0.0247 (13)	−0.0063 (11)	0.0010 (10)	−0.0023 (10)
C2	0.0386 (15)	0.0294 (15)	0.0280 (13)	0.0054 (11)	0.0002 (11)	−0.0052 (11)
C3	0.0273 (14)	0.0391 (15)	0.0243 (13)	0.0052 (11)	0.0007 (9)	−0.0021 (11)
C4	0.0251 (13)	0.0359 (15)	0.0245 (13)	−0.0010 (10)	−0.0023 (9)	0.0032 (10)
Br1	0.03307 (14)	0.03829 (15)	0.03322 (13)	−0.00806 (14)	0.00551 (8)	0.00331 (14)
C5	0.0282 (13)	0.0313 (14)	0.0287 (13)	0.0011 (10)	0.0002 (10)	−0.0026 (10)
C6	0.0262 (14)	0.0331 (16)	0.0303 (15)	−0.0006 (10)	0.0046 (11)	−0.0042 (10)
O1	0.0563 (14)	0.0341 (12)	0.0371 (11)	−0.0187 (10)	0.0085 (9)	−0.0103 (9)
C1'	0.0323 (14)	0.0217 (13)	0.0390 (15)	0.0000 (10)	0.0033 (11)	−0.0005 (10)
C2'	0.0329 (14)	0.0243 (14)	0.0450 (16)	−0.0025 (10)	−0.0055 (11)	−0.0002 (11)
C3'	0.0275 (16)	0.0267 (14)	0.0523 (19)	−0.0029 (10)	−0.0002 (11)	0.0068 (12)
C4'	0.0350 (15)	0.0297 (14)	0.0399 (15)	0.0017 (11)	0.0053 (11)	0.0065 (11)
F1	0.0591 (12)	0.0466 (11)	0.0436 (10)	−0.0088 (9)	0.0133 (8)	0.0082 (8)
C5'	0.0386 (16)	0.0312 (15)	0.0410 (16)	−0.0013 (11)	−0.0049 (12)	−0.0003 (12)
C6'	0.0328 (15)	0.0268 (14)	0.0415 (16)	−0.0023 (10)	0.0022 (10)	−0.0016 (11)

Geometric parameters (Å, º)

C1—C6	1.379 (4)	O1—C1'	1.384 (3)
C1—C2	1.383 (4)	C1'—C2'	1.381 (4)
C1—O1	1.395 (4)	C1'—C6'	1.388 (4)
C2—C3	1.392 (4)	C2'—C3'	1.385 (4)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.390 (4)	C3'—C4'	1.376 (4)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.374 (4)	C4'—F1	1.354 (3)
C4—Br1	1.897 (3)	C4'—C5'	1.376 (4)
C5—C6	1.386 (4)	C5'—C6'	1.395 (4)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
C6—C1—C2	121.3 (3)	C2'—C1'—O1	116.3 (3)
C6—C1—O1	121.1 (3)	C2'—C1'—C6'	120.9 (3)
C2—C1—O1	117.5 (3)	O1—C1'—C6'	122.7 (3)
C1—C2—C3	119.3 (3)	C1'—C2'—C3'	120.1 (3)
C1—C2—H2	120.3	C1'—C2'—H2'	119.9
C3—C2—H2	120.3	C3'—C2'—H2'	119.9
C4—C3—C2	118.8 (3)	C4'—C3'—C2'	118.7 (3)
C4—C3—H3	120.6	C4'—C3'—H3'	120.7
C2—C3—H3	120.6	C2'—C3'—H3'	120.7
C5—C4—C3	121.7 (3)	F1—C4'—C5'	118.7 (3)
C5—C4—Br1	118.8 (2)	F1—C4'—C3'	119.1 (3)
C3—C4—Br1	119.4 (2)	C5'—C4'—C3'	122.2 (3)
C4—C5—C6	119.3 (3)	C4'—C5'—C6'	119.1 (3)
C4—C5—H5	120.4	C4'—C5'—H5'	120.5
C6—C5—H5	120.4	C6'—C5'—H5'	120.5
C1—C6—C5	119.6 (3)	C1'—C6'—C5'	119.0 (3)
C1—C6—H6	120.2	C1'—C6'—H6'	120.5
C5—C6—H6	120.2	C5'—C6'—H6'	120.5
C1'—O1—C1	118.1 (2)
C6—C1—C2—C3	−2.1 (4)	C1—O1—C1'—C2'	−154.5 (3)
O1—C1—C2—C3	−178.4 (2)	C1—O1—C1'—C6'	29.2 (4)
C1—C2—C3—C4	1.2 (4)	O1—C1'—C2'—C3'	−177.5 (3)
C2—C3—C4—C5	0.4 (4)	C6'—C1'—C2'—C3'	−1.0 (4)
C2—C3—C4—Br1	−178.8 (2)	C1'—C2'—C3'—C4'	−0.1 (4)
C3—C4—C5—C6	−1.1 (4)	C2'—C3'—C4'—F1	−178.7 (3)
Br1—C4—C5—C6	178.2 (2)	C2'—C3'—C4'—C5'	0.5 (5)
C2—C1—C6—C5	1.5 (4)	F1—C4'—C5'—C6'	179.4 (3)
O1—C1—C6—C5	177.6 (2)	C3'—C4'—C5'—C6'	0.2 (5)
C4—C5—C6—C1	0.1 (4)	C2'—C1'—C6'—C5'	1.7 (4)
C6—C1—O1—C1'	55.9 (4)	O1—C1'—C6'—C5'	177.9 (3)
C2—C1—O1—C1'	−127.9 (3)	C4'—C5'—C6'—C1'	−1.3 (4)