The title compound, C13H11BBrFO3, exists as an almost centrosymmetric dimer of two crystallographically independent molecules linked by hydrogen bonds. The B(OH)2 groups are slightly twisted from the plane of the benzene ring. There are intra- and intermolecular hydrogen bonds.
Supporting information
CCDC reference: 605232
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.008 Å
- R factor = 0.049
- wR factor = 0.113
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.23
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2O' .. F1' .. 2.59 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.
3-Bromo-2-(2-fluorobenzyloxy)phenylboronic acid
top
Crystal data top
C13H11BBrFO3 | F(000) = 648 |
Mr = 324.94 | Dx = 1.678 Mg m−3 |
Triclinic, P1 | Melting point = 112.0–114.0 K |
a = 4.0226 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.278 (2) Å | Cell parameters from 10000 reflections |
c = 21.685 (3) Å | θ = 1.5–29.7° |
α = 105.084 (11)° | µ = 3.21 mm−1 |
β = 90.026 (10)° | T = 100 K |
γ = 92.089 (11)° | Needle, colourless |
V = 1285.9 (3) Å3 | 0.53 × 0.07 × 0.05 mm |
Z = 4 | |
Data collection top
Oxford Diffraction KM-4-CCD diffractometer | 4521 independent reflections |
Radiation source: fine-focus sealed tube | 2963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 1024 pixels mm-1 | θmax = 25.0°, θmin = 2.9° |
ω scans | h = −4→4 |
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2001) | k = −18→18 |
Tmin = 0.522, Tmax = 0.857 | l = −25→25 |
13268 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
4521 reflections | (Δ/σ)max = 0.014 |
347 parameters | Δρmax = 1.66 e Å−3 |
156 restraints | Δρmin = −0.74 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.66925 (13) | 0.45022 (3) | 0.17811 (3) | 0.01804 (17) | |
Br1' | 0.16302 (13) | 0.52661 (4) | 0.32487 (3) | 0.02040 (17) | |
F1 | 0.4200 (9) | 0.0743 (2) | 0.18014 (16) | 0.0343 (9) | |
F1' | −0.0198 (9) | 0.9072 (2) | 0.30262 (17) | 0.0383 (9) | |
O1 | −0.0635 (10) | 0.1027 (2) | −0.0356 (2) | 0.0309 (10) | |
H1O | −0.0935 | 0.0466 | −0.0405 | 0.046* | |
O2 | 0.2289 (10) | 0.0821 (2) | 0.05303 (18) | 0.0230 (9) | |
H2O | 0.3458 | 0.1124 | 0.0838 | 0.035* | |
O3 | 0.4967 (8) | 0.2460 (2) | 0.13364 (17) | 0.0156 (8) | |
O1' | −0.1992 (10) | 0.9085 (2) | 0.53907 (18) | 0.0266 (10) | |
H1O' | −0.1749 | 0.9644 | 0.5421 | 0.040* | |
O2' | 0.0710 (10) | 0.9050 (2) | 0.44218 (18) | 0.0257 (10) | |
H2O' | 0.1240 | 0.8671 | 0.4084 | 0.039* | |
O3' | 0.1281 (8) | 0.7336 (2) | 0.36124 (17) | 0.0160 (8) | |
C1 | 0.4484 (12) | 0.3843 (3) | 0.1014 (3) | 0.0169 (12) | |
C2 | 0.3447 (12) | 0.4307 (3) | 0.0581 (3) | 0.0157 (12) | |
H2 | 0.3857 | 0.4943 | 0.0663 | 0.019* | |
C3 | 0.1820 (12) | 0.3832 (3) | 0.0034 (3) | 0.0179 (13) | |
H3 | 0.1106 | 0.4144 | −0.0265 | 0.021* | |
C4 | 0.1202 (12) | 0.2908 (3) | −0.0090 (3) | 0.0147 (12) | |
H4 | 0.0081 | 0.2594 | −0.0474 | 0.018* | |
C5 | 0.2195 (13) | 0.2427 (3) | 0.0340 (3) | 0.0148 (12) | |
C6 | 0.3826 (13) | 0.2914 (3) | 0.0902 (3) | 0.0164 (12) | |
C7 | 0.2811 (12) | 0.2550 (4) | 0.1890 (2) | 0.0160 (12) | |
H7A | 0.0777 | 0.2157 | 0.1770 | 0.019* | |
H7B | 0.2142 | 0.3186 | 0.2049 | 0.019* | |
C8 | 0.4709 (12) | 0.2272 (3) | 0.2399 (3) | 0.0154 (12) | |
C9 | 0.5897 (13) | 0.2886 (4) | 0.2952 (3) | 0.0184 (13) | |
H9 | 0.5589 | 0.3515 | 0.3005 | 0.022* | |
C10 | 0.7514 (13) | 0.2610 (4) | 0.3430 (3) | 0.0230 (14) | |
H10 | 0.8270 | 0.3046 | 0.3805 | 0.028* | |
C11 | 0.8026 (13) | 0.1700 (4) | 0.3357 (3) | 0.0214 (13) | |
H11 | 0.9149 | 0.1509 | 0.3682 | 0.026* | |
C12 | 0.6902 (14) | 0.1070 (4) | 0.2812 (3) | 0.0262 (15) | |
H12 | 0.7218 | 0.0441 | 0.2759 | 0.031* | |
C13 | 0.5319 (14) | 0.1370 (4) | 0.2349 (3) | 0.0233 (14) | |
C1' | −0.0120 (12) | 0.6037 (3) | 0.4000 (3) | 0.0167 (12) | |
C2' | −0.1468 (12) | 0.5645 (4) | 0.4457 (3) | 0.0174 (13) | |
H2' | −0.1556 | 0.5005 | 0.4389 | 0.021* | |
C3' | −0.2695 (12) | 0.6206 (4) | 0.5018 (3) | 0.0191 (13) | |
H3' | −0.3648 | 0.5946 | 0.5333 | 0.023* | |
C4' | −0.2530 (13) | 0.7140 (4) | 0.5118 (3) | 0.0185 (13) | |
H4' | −0.3338 | 0.7514 | 0.5506 | 0.022* | |
C5' | −0.1190 (13) | 0.7543 (4) | 0.4656 (3) | 0.0176 (13) | |
C6' | −0.0042 (12) | 0.6967 (3) | 0.4093 (3) | 0.0146 (12) | |
C7' | −0.1098 (12) | 0.7277 (4) | 0.3086 (3) | 0.0185 (13) | |
H7A' | −0.2944 | 0.7689 | 0.3234 | 0.022* | |
H7B' | −0.2043 | 0.6649 | 0.2934 | 0.022* | |
C8' | 0.0713 (12) | 0.7541 (3) | 0.2561 (3) | 0.0146 (12) | |
C9' | 0.2103 (12) | 0.6894 (4) | 0.2059 (3) | 0.0181 (13) | |
H9' | 0.1968 | 0.6273 | 0.2061 | 0.022* | |
C10' | 0.3669 (13) | 0.7142 (4) | 0.1559 (3) | 0.0226 (14) | |
H10' | 0.4577 | 0.6692 | 0.1219 | 0.027* | |
C11' | 0.3911 (13) | 0.8045 (4) | 0.1555 (3) | 0.0251 (14) | |
H11' | 0.4994 | 0.8217 | 0.1213 | 0.030* | |
C12' | 0.2584 (14) | 0.8698 (4) | 0.2048 (3) | 0.0289 (15) | |
H12' | 0.2726 | 0.9319 | 0.2047 | 0.035* | |
C13' | 0.1056 (14) | 0.8432 (4) | 0.2537 (3) | 0.0221 (13) | |
B1 | 0.1266 (16) | 0.1378 (4) | 0.0167 (3) | 0.0189 (15) | |
B1' | −0.0826 (16) | 0.8609 (4) | 0.4818 (3) | 0.0176 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0163 (3) | 0.0166 (3) | 0.0190 (3) | −0.0009 (2) | 0.0001 (2) | 0.0007 (2) |
Br1' | 0.0201 (3) | 0.0183 (3) | 0.0203 (3) | 0.0036 (2) | 0.0013 (3) | 0.0002 (2) |
F1 | 0.059 (2) | 0.0155 (17) | 0.027 (2) | −0.0038 (16) | −0.0161 (18) | 0.0044 (16) |
F1' | 0.061 (3) | 0.0241 (19) | 0.031 (2) | 0.0093 (17) | 0.0081 (19) | 0.0076 (17) |
O1 | 0.043 (3) | 0.020 (2) | 0.029 (3) | −0.007 (2) | −0.016 (2) | 0.005 (2) |
O2 | 0.040 (3) | 0.015 (2) | 0.014 (2) | −0.0024 (17) | −0.0088 (19) | 0.0046 (17) |
O3 | 0.018 (2) | 0.0163 (19) | 0.015 (2) | 0.0055 (15) | 0.0066 (17) | 0.0076 (16) |
O1' | 0.044 (3) | 0.016 (2) | 0.019 (2) | 0.0006 (19) | 0.011 (2) | 0.0028 (18) |
O2' | 0.043 (3) | 0.017 (2) | 0.016 (2) | −0.0028 (19) | 0.006 (2) | 0.0013 (18) |
O3' | 0.019 (2) | 0.021 (2) | 0.010 (2) | −0.0001 (16) | 0.0018 (16) | 0.0067 (16) |
C1 | 0.010 (3) | 0.019 (3) | 0.020 (3) | 0.001 (2) | 0.004 (2) | 0.003 (2) |
C2 | 0.011 (3) | 0.010 (3) | 0.026 (3) | −0.003 (2) | 0.001 (2) | 0.004 (2) |
C3 | 0.011 (3) | 0.012 (3) | 0.030 (4) | 0.004 (2) | 0.002 (3) | 0.005 (3) |
C4 | 0.012 (3) | 0.023 (3) | 0.010 (3) | 0.002 (2) | 0.000 (2) | 0.007 (2) |
C5 | 0.018 (3) | 0.018 (3) | 0.009 (3) | 0.001 (2) | 0.006 (2) | 0.004 (2) |
C6 | 0.016 (3) | 0.020 (3) | 0.017 (3) | 0.004 (2) | 0.008 (2) | 0.011 (3) |
C7 | 0.011 (3) | 0.028 (3) | 0.012 (3) | 0.001 (2) | 0.002 (2) | 0.011 (3) |
C8 | 0.012 (3) | 0.022 (3) | 0.014 (3) | 0.000 (2) | 0.004 (2) | 0.009 (2) |
C9 | 0.019 (3) | 0.018 (3) | 0.019 (3) | 0.006 (2) | 0.006 (3) | 0.005 (3) |
C10 | 0.020 (3) | 0.033 (3) | 0.017 (3) | 0.001 (3) | 0.002 (3) | 0.009 (3) |
C11 | 0.018 (3) | 0.036 (4) | 0.015 (3) | −0.002 (3) | −0.004 (3) | 0.014 (3) |
C12 | 0.030 (4) | 0.019 (3) | 0.036 (4) | 0.004 (3) | 0.000 (3) | 0.018 (3) |
C13 | 0.026 (3) | 0.029 (3) | 0.016 (3) | −0.003 (3) | 0.000 (3) | 0.008 (3) |
C1' | 0.010 (3) | 0.019 (3) | 0.019 (3) | 0.003 (2) | −0.003 (2) | 0.001 (2) |
C2' | 0.018 (3) | 0.019 (3) | 0.014 (3) | −0.003 (2) | −0.003 (3) | 0.004 (2) |
C3' | 0.012 (3) | 0.022 (3) | 0.029 (4) | −0.003 (2) | 0.006 (3) | 0.017 (3) |
C4' | 0.014 (3) | 0.032 (3) | 0.009 (3) | −0.003 (2) | 0.000 (2) | 0.006 (3) |
C5' | 0.014 (3) | 0.021 (3) | 0.016 (3) | 0.002 (2) | 0.000 (2) | 0.003 (3) |
C6' | 0.009 (3) | 0.020 (3) | 0.015 (3) | 0.000 (2) | 0.002 (2) | 0.005 (2) |
C7' | 0.008 (3) | 0.031 (3) | 0.017 (3) | 0.006 (2) | −0.001 (2) | 0.006 (3) |
C8' | 0.009 (3) | 0.022 (3) | 0.014 (3) | 0.002 (2) | −0.003 (2) | 0.008 (2) |
C9' | 0.012 (3) | 0.027 (3) | 0.016 (3) | −0.002 (2) | −0.002 (2) | 0.009 (3) |
C10' | 0.023 (3) | 0.038 (4) | 0.007 (3) | 0.003 (3) | −0.004 (3) | 0.005 (3) |
C11' | 0.019 (3) | 0.045 (4) | 0.013 (3) | −0.002 (3) | 0.003 (3) | 0.012 (3) |
C12' | 0.032 (4) | 0.025 (3) | 0.035 (4) | −0.009 (3) | −0.005 (3) | 0.017 (3) |
C13' | 0.025 (3) | 0.022 (3) | 0.021 (3) | 0.001 (3) | −0.001 (3) | 0.008 (3) |
B1 | 0.022 (4) | 0.021 (3) | 0.015 (4) | 0.002 (3) | 0.001 (3) | 0.007 (3) |
B1' | 0.021 (4) | 0.022 (3) | 0.013 (4) | 0.005 (3) | 0.001 (3) | 0.010 (3) |
Geometric parameters (Å, º) top
Br1—C1 | 1.906 (6) | C9—C10 | 1.385 (7) |
Br1'—C1' | 1.897 (5) | C9—H9 | 0.9500 |
F1—C13 | 1.381 (6) | C10—C11 | 1.381 (7) |
F1'—C13' | 1.353 (6) | C10—H10 | 0.9500 |
O1—B1 | 1.346 (7) | C11—C12 | 1.380 (8) |
O1—H1O | 0.8400 | C11—H11 | 0.9500 |
O2—B1 | 1.375 (7) | C12—C13 | 1.373 (8) |
O2—H2O | 0.8400 | C12—H12 | 0.9500 |
O3—C6 | 1.394 (6) | C1'—C6' | 1.381 (7) |
O3—C7 | 1.461 (6) | C1'—C2' | 1.386 (7) |
O1'—B1' | 1.358 (7) | C2'—C3' | 1.395 (7) |
O1'—H1O' | 0.8400 | C2'—H2' | 0.9500 |
O2'—B1' | 1.359 (7) | C3'—C4' | 1.386 (7) |
O2'—H2O' | 0.8400 | C3'—H3' | 0.9500 |
O3'—C6' | 1.403 (6) | C4'—C5' | 1.404 (7) |
O3'—C7' | 1.471 (6) | C4'—H4' | 0.9500 |
C1—C2 | 1.386 (7) | C5'—C6' | 1.397 (7) |
C1—C6 | 1.391 (7) | C5'—B1' | 1.575 (8) |
C2—C3 | 1.371 (7) | C7'—C8' | 1.487 (7) |
C2—H2 | 0.9500 | C7'—H7A' | 0.9900 |
C3—C4 | 1.379 (7) | C7'—H7B' | 0.9900 |
C3—H3 | 0.9500 | C8'—C13' | 1.377 (7) |
C4—C5 | 1.394 (7) | C8'—C9' | 1.398 (7) |
C4—H4 | 0.9500 | C9'—C10' | 1.382 (7) |
C5—C6 | 1.401 (7) | C9'—H9' | 0.9500 |
C5—B1 | 1.579 (8) | C10'—C11' | 1.382 (8) |
C7—C8 | 1.499 (7) | C10'—H10' | 0.9500 |
C7—H7A | 0.9900 | C11'—C12' | 1.380 (8) |
C7—H7B | 0.9900 | C11'—H11' | 0.9500 |
C8—C13 | 1.386 (7) | C12'—C13' | 1.370 (8) |
C8—C9 | 1.389 (7) | C12'—H12' | 0.9500 |
| | | |
B1—O1—H1O | 109.5 | C6'—C1'—C2' | 120.6 (5) |
B1—O2—H2O | 109.5 | C6'—C1'—Br1' | 121.0 (4) |
C6—O3—C7 | 113.0 (4) | C2'—C1'—Br1' | 118.3 (4) |
B1'—O1'—H1O' | 109.5 | C1'—C2'—C3' | 118.9 (5) |
B1'—O2'—H2O' | 109.5 | C1'—C2'—H2' | 120.5 |
C6'—O3'—C7' | 112.5 (4) | C3'—C2'—H2' | 120.5 |
C2—C1—C6 | 120.7 (5) | C4'—C3'—C2' | 120.4 (5) |
C2—C1—Br1 | 119.1 (4) | C4'—C3'—H3' | 119.8 |
C6—C1—Br1 | 120.1 (4) | C2'—C3'—H3' | 119.8 |
C3—C2—C1 | 118.9 (5) | C3'—C4'—C5' | 121.1 (5) |
C3—C2—H2 | 120.6 | C3'—C4'—H4' | 119.5 |
C1—C2—H2 | 120.6 | C5'—C4'—H4' | 119.5 |
C2—C3—C4 | 121.1 (5) | C6'—C5'—C4' | 117.5 (5) |
C2—C3—H3 | 119.4 | C6'—C5'—B1' | 123.7 (5) |
C4—C3—H3 | 119.4 | C4'—C5'—B1' | 118.7 (5) |
C3—C4—C5 | 121.1 (5) | C1'—C6'—C5' | 121.5 (5) |
C3—C4—H4 | 119.5 | C1'—C6'—O3' | 118.9 (5) |
C5—C4—H4 | 119.5 | C5'—C6'—O3' | 119.7 (4) |
C4—C5—C6 | 117.8 (5) | O3'—C7'—C8' | 108.0 (4) |
C4—C5—B1 | 117.3 (5) | O3'—C7'—H7A' | 110.1 |
C6—C5—B1 | 124.9 (5) | C8'—C7'—H7A' | 110.1 |
C1—C6—O3 | 119.6 (5) | O3'—C7'—H7B' | 110.1 |
C1—C6—C5 | 120.4 (5) | C8'—C7'—H7B' | 110.1 |
O3—C6—C5 | 119.9 (4) | H7A'—C7'—H7B' | 108.4 |
O3—C7—C8 | 108.1 (4) | C13'—C8'—C9' | 116.7 (5) |
O3—C7—H7A | 110.1 | C13'—C8'—C7' | 121.8 (5) |
C8—C7—H7A | 110.1 | C9'—C8'—C7' | 121.5 (5) |
O3—C7—H7B | 110.1 | C10'—C9'—C8' | 121.2 (5) |
C8—C7—H7B | 110.1 | C10'—C9'—H9' | 119.4 |
H7A—C7—H7B | 108.4 | C8'—C9'—H9' | 119.4 |
C13—C8—C9 | 115.6 (5) | C11'—C10'—C9' | 119.8 (5) |
C13—C8—C7 | 121.3 (5) | C11'—C10'—H10' | 120.1 |
C9—C8—C7 | 123.1 (5) | C9'—C10'—H10' | 120.1 |
C10—C9—C8 | 122.1 (5) | C12'—C11'—C10' | 120.2 (5) |
C10—C9—H9 | 119.0 | C12'—C11'—H11' | 119.9 |
C8—C9—H9 | 119.0 | C10'—C11'—H11' | 119.9 |
C11—C10—C9 | 119.8 (6) | C13'—C12'—C11' | 118.7 (5) |
C11—C10—H10 | 120.1 | C13'—C12'—H12' | 120.6 |
C9—C10—H10 | 120.1 | C11'—C12'—H12' | 120.6 |
C12—C11—C10 | 119.9 (5) | F1'—C13'—C12' | 118.9 (5) |
C12—C11—H11 | 120.1 | F1'—C13'—C8' | 117.7 (5) |
C10—C11—H11 | 120.1 | C12'—C13'—C8' | 123.4 (5) |
C13—C12—C11 | 118.6 (5) | O1—B1—O2 | 119.4 (5) |
C13—C12—H12 | 120.7 | O1—B1—C5 | 117.9 (5) |
C11—C12—H12 | 120.7 | O2—B1—C5 | 122.7 (5) |
C12—C13—F1 | 118.9 (5) | O1'—B1'—O2' | 120.1 (5) |
C12—C13—C8 | 124.0 (6) | O1'—B1'—C5' | 117.4 (5) |
F1—C13—C8 | 117.1 (5) | O2'—B1'—C5' | 122.4 (5) |
| | | |
C6—C1—C2—C3 | −1.4 (8) | C3'—C4'—C5'—C6' | 0.2 (8) |
Br1—C1—C2—C3 | −179.1 (4) | C3'—C4'—C5'—B1' | −175.5 (5) |
C1—C2—C3—C4 | 0.2 (8) | C2'—C1'—C6'—C5' | 2.5 (8) |
C2—C3—C4—C5 | 0.4 (8) | Br1'—C1'—C6'—C5' | −177.1 (4) |
C3—C4—C5—C6 | 0.3 (7) | C2'—C1'—C6'—O3' | −178.7 (5) |
C3—C4—C5—B1 | 178.0 (5) | Br1'—C1'—C6'—O3' | 1.6 (7) |
C2—C1—C6—O3 | 178.4 (4) | C4'—C5'—C6'—C1' | −2.0 (8) |
Br1—C1—C6—O3 | −3.8 (6) | B1'—C5'—C6'—C1' | 173.4 (5) |
C2—C1—C6—C5 | 2.0 (8) | C4'—C5'—C6'—O3' | 179.2 (4) |
Br1—C1—C6—C5 | 179.8 (4) | B1'—C5'—C6'—O3' | −5.4 (8) |
C7—O3—C6—C1 | 81.5 (6) | C7'—O3'—C6'—C1' | 79.9 (6) |
C7—O3—C6—C5 | −102.1 (5) | C7'—O3'—C6'—C5' | −101.3 (5) |
C4—C5—C6—C1 | −1.5 (7) | C6'—O3'—C7'—C8' | −170.8 (4) |
B1—C5—C6—C1 | −179.0 (5) | O3'—C7'—C8'—C13' | −87.3 (6) |
C4—C5—C6—O3 | −177.8 (4) | O3'—C7'—C8'—C9' | 93.9 (6) |
B1—C5—C6—O3 | 4.7 (8) | C13'—C8'—C9'—C10' | −1.5 (8) |
C6—O3—C7—C8 | −164.3 (4) | C7'—C8'—C9'—C10' | 177.4 (5) |
O3—C7—C8—C13 | −73.5 (6) | C8'—C9'—C10'—C11' | 0.8 (8) |
O3—C7—C8—C9 | 108.1 (5) | C9'—C10'—C11'—C12' | −0.2 (8) |
C13—C8—C9—C10 | −1.5 (8) | C10'—C11'—C12'—C13' | 0.5 (9) |
C7—C8—C9—C10 | 177.0 (5) | C11'—C12'—C13'—F1' | 178.9 (5) |
C8—C9—C10—C11 | 0.9 (8) | C11'—C12'—C13'—C8' | −1.3 (9) |
C9—C10—C11—C12 | −0.5 (8) | C9'—C8'—C13'—F1' | −178.4 (5) |
C10—C11—C12—C13 | 0.7 (8) | C7'—C8'—C13'—F1' | 2.7 (8) |
C11—C12—C13—F1 | 179.8 (5) | C9'—C8'—C13'—C12' | 1.7 (8) |
C11—C12—C13—C8 | −1.4 (9) | C7'—C8'—C13'—C12' | −177.2 (5) |
C9—C8—C13—C12 | 1.7 (8) | C4—C5—B1—O1 | −4.9 (8) |
C7—C8—C13—C12 | −176.8 (5) | C6—C5—B1—O1 | 172.5 (5) |
C9—C8—C13—F1 | −179.4 (5) | C4—C5—B1—O2 | 175.7 (5) |
C7—C8—C13—F1 | 2.1 (8) | C6—C5—B1—O2 | −6.8 (9) |
C6'—C1'—C2'—C3' | −1.1 (8) | C6'—C5'—B1'—O1' | −178.6 (5) |
Br1'—C1'—C2'—C3' | 178.6 (4) | C4'—C5'—B1'—O1' | −3.2 (8) |
C1'—C2'—C3'—C4' | −0.7 (8) | C6'—C5'—B1'—O2' | −1.3 (9) |
C2'—C3'—C4'—C5' | 1.2 (8) | C4'—C5'—B1'—O2' | 174.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.84 | 1.97 | 2.803 (5) | 172 |
O2—H2O···O3 | 0.84 | 2.11 | 2.830 (5) | 143 |
O2—H2O···F1 | 0.84 | 2.33 | 2.895 (5) | 125 |
O1′—H1O′···O2′ii | 0.84 | 1.97 | 2.800 (5) | 172 |
O2′—H2O′···O3′ | 0.84 | 2.03 | 2.764 (5) | 146 |
O2′—H2O′···F1′ | 0.84 | 2.59 | 3.057 (5) | 116 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+2, −z+1. |