Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031083/is6018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031083/is6018Isup2.hkl |
CCDC reference: 262299
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C21H29BrO3 | F(000) = 1712 |
Mr = 409.35 | Dx = 1.352 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 22.565 (7) Å | Cell parameters from 2865 reflections |
b = 9.393 (3) Å | θ = 2.4–21.6° |
c = 21.052 (7) Å | µ = 2.06 mm−1 |
β = 115.682 (8)° | T = 293 K |
V = 4021 (2) Å3 | Needle, colorless |
Z = 8 | 0.24 × 0.18 × 0.14 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 6647 independent reflections |
Radiation source: fine-focus sealed tube | 4103 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −23→26 |
Tmin = 0.605, Tmax = 0.749 | k = −10→11 |
10528 measured reflections | l = −23→25 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
6647 reflections | Δρmax = 0.57 e Å−3 |
459 parameters | Δρmin = −0.50 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2214 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.012 (9) |
Experimental. The melting point measured by DSC is 469.25 K. |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.43123 (3) | 0.25640 (7) | 0.02031 (3) | 0.0734 (2) | |
Br2 | 0.07052 (4) | −0.31301 (7) | 0.42330 (3) | 0.0931 (3) | |
O1 | 0.25906 (19) | −0.3337 (5) | 0.39598 (18) | 0.0711 (12) | |
O2 | 0.41558 (19) | 0.5390 (4) | 0.14409 (19) | 0.0670 (12) | |
O3 | 0.27481 (15) | 0.3550 (4) | 0.05811 (15) | 0.0441 (9) | |
H3 | 0.2649 | 0.4089 | 0.0826 | 0.066* | |
O4 | 0.20637 (18) | 0.5286 (4) | 0.11173 (17) | 0.0609 (11) | |
O5 | 0.0828 (2) | 0.0739 (6) | 0.5140 (2) | 0.0868 (14) | |
O6 | 0.20916 (17) | −0.0036 (4) | 0.48219 (16) | 0.0577 (10) | |
H6 | 0.2179 | 0.0595 | 0.5118 | 0.086* | |
C1 | 0.3261 (3) | −0.0075 (5) | 0.3614 (2) | 0.0485 (14) | |
H1A | 0.3522 | 0.0715 | 0.3891 | 0.058* | |
H1B | 0.2820 | 0.0277 | 0.3328 | 0.058* | |
C2 | 0.3228 (3) | −0.1232 (6) | 0.4116 (3) | 0.0616 (17) | |
H2A | 0.3671 | −0.1478 | 0.4452 | 0.074* | |
H2B | 0.3000 | −0.0856 | 0.4378 | 0.074* | |
C3 | 0.2887 (3) | −0.2532 (7) | 0.3735 (3) | 0.0562 (15) | |
C4 | 0.2947 (2) | −0.2857 (6) | 0.3086 (2) | 0.0554 (16) | |
H4 | 0.2743 | −0.3675 | 0.2840 | 0.067* | |
C5 | 0.3276 (2) | −0.2053 (5) | 0.2825 (2) | 0.0430 (13) | |
C6 | 0.3399 (3) | −0.2607 (6) | 0.2214 (2) | 0.0567 (15) | |
H6A | 0.3857 | −0.2877 | 0.2385 | 0.068* | |
H6B | 0.3133 | −0.3448 | 0.2018 | 0.068* | |
C7 | 0.3235 (3) | −0.1497 (5) | 0.1644 (3) | 0.0549 (15) | |
H7A | 0.2763 | −0.1352 | 0.1420 | 0.066* | |
H7B | 0.3363 | −0.1851 | 0.1289 | 0.066* | |
C8 | 0.3572 (2) | −0.0071 (5) | 0.1916 (2) | 0.0387 (12) | |
H8 | 0.4049 | −0.0220 | 0.2127 | 0.046* | |
C9 | 0.3378 (2) | 0.0476 (5) | 0.2500 (2) | 0.0358 (12) | |
H9 | 0.2897 | 0.0543 | 0.2278 | 0.043* | |
C10 | 0.3560 (2) | −0.0614 (5) | 0.3122 (2) | 0.0363 (12) | |
C11 | 0.3631 (3) | 0.1984 (5) | 0.2749 (2) | 0.0474 (13) | |
H11A | 0.4104 | 0.1945 | 0.3023 | 0.057* | |
H11B | 0.3444 | 0.2314 | 0.3060 | 0.057* | |
C12 | 0.3470 (3) | 0.3077 (5) | 0.2153 (2) | 0.0405 (13) | |
H12A | 0.3683 | 0.3975 | 0.2348 | 0.049* | |
H12B | 0.2999 | 0.3239 | 0.1920 | 0.049* | |
C13 | 0.3708 (2) | 0.2533 (6) | 0.16113 (19) | 0.0338 (11) | |
C14 | 0.3462 (2) | 0.3358 (5) | 0.0901 (2) | 0.0368 (12) | |
C15 | 0.3535 (2) | 0.2239 (5) | 0.0393 (2) | 0.0395 (14) | |
H15 | 0.3141 | 0.2283 | −0.0056 | 0.047* | |
C16 | 0.3560 (3) | 0.0755 (5) | 0.0722 (2) | 0.0431 (14) | |
H16A | 0.3238 | 0.0119 | 0.0386 | 0.052* | |
H16B | 0.3993 | 0.0333 | 0.0881 | 0.052* | |
C17 | 0.3398 (2) | 0.1060 (5) | 0.1350 (2) | 0.0356 (12) | |
H17 | 0.2921 | 0.1191 | 0.1152 | 0.043* | |
C18 | 0.4316 (3) | −0.0779 (6) | 0.3549 (3) | 0.0581 (16) | |
H18A | 0.4408 | −0.1507 | 0.3899 | 0.087* | |
H18B | 0.4502 | 0.0107 | 0.3775 | 0.087* | |
H18C | 0.4506 | −0.1040 | 0.3236 | 0.087* | |
C19 | 0.4474 (2) | 0.2438 (6) | 0.1963 (2) | 0.0502 (13) | |
H19A | 0.4657 | 0.3368 | 0.2117 | 0.075* | |
H19B | 0.4620 | 0.2080 | 0.1628 | 0.075* | |
H19C | 0.4617 | 0.1808 | 0.2361 | 0.075* | |
C20 | 0.3753 (3) | 0.4851 (6) | 0.0911 (3) | 0.0444 (14) | |
C21 | 0.3464 (3) | 0.5675 (6) | 0.0220 (3) | 0.0680 (17) | |
H21A | 0.3115 | 0.6276 | 0.0206 | 0.102* | |
H21B | 0.3295 | 0.5018 | −0.0168 | 0.102* | |
H21C | 0.3801 | 0.6250 | 0.0186 | 0.102* | |
C22 | 0.1278 (3) | 0.4831 (6) | 0.2246 (3) | 0.0532 (15) | |
H22A | 0.1032 | 0.5407 | 0.2432 | 0.064* | |
H22B | 0.1719 | 0.4717 | 0.2618 | 0.064* | |
C23 | 0.1321 (3) | 0.5635 (6) | 0.1638 (2) | 0.0561 (15) | |
H23A | 0.0881 | 0.5850 | 0.1282 | 0.067* | |
H23B | 0.1552 | 0.6527 | 0.1809 | 0.067* | |
C24 | 0.1677 (3) | 0.4756 (6) | 0.1320 (2) | 0.0452 (13) | |
C25 | 0.1539 (3) | 0.3231 (6) | 0.1271 (2) | 0.0520 (15) | |
H25 | 0.1703 | 0.2670 | 0.1020 | 0.062* | |
C26 | 0.1188 (2) | 0.2590 (7) | 0.1567 (2) | 0.0441 (12) | |
C27 | 0.1013 (3) | 0.1036 (6) | 0.1440 (3) | 0.0594 (16) | |
H27A | 0.1221 | 0.0637 | 0.1161 | 0.071* | |
H27B | 0.0541 | 0.0945 | 0.1169 | 0.071* | |
C28 | 0.1230 (3) | 0.0169 (6) | 0.2130 (3) | 0.0525 (16) | |
H28A | 0.1057 | −0.0792 | 0.2020 | 0.063* | |
H28B | 0.1706 | 0.0109 | 0.2362 | 0.063* | |
C29 | 0.0985 (2) | 0.0858 (5) | 0.2621 (2) | 0.0413 (13) | |
H29 | 0.0505 | 0.0786 | 0.2410 | 0.050* | |
C30 | 0.1179 (2) | 0.2443 (6) | 0.2744 (2) | 0.0408 (12) | |
H30 | 0.1661 | 0.2464 | 0.2965 | 0.049* | |
C31 | 0.0955 (3) | 0.3363 (6) | 0.2056 (2) | 0.0437 (14) | |
C32 | 0.0968 (3) | 0.3122 (6) | 0.3280 (2) | 0.0558 (16) | |
H32A | 0.0492 | 0.3159 | 0.3076 | 0.067* | |
H32B | 0.1131 | 0.4092 | 0.3373 | 0.067* | |
C33 | 0.1225 (3) | 0.2296 (5) | 0.3985 (2) | 0.0551 (15) | |
H33A | 0.1701 | 0.2368 | 0.4224 | 0.066* | |
H33B | 0.1048 | 0.2720 | 0.4286 | 0.066* | |
C34 | 0.1027 (2) | 0.0732 (5) | 0.3863 (2) | 0.0448 (13) | |
C35 | 0.1386 (2) | −0.0297 (6) | 0.4496 (2) | 0.0454 (13) | |
C36 | 0.1337 (3) | −0.1766 (6) | 0.4155 (3) | 0.0559 (15) | |
H36 | 0.1774 | −0.2205 | 0.4373 | 0.067* | |
C37 | 0.1162 (3) | −0.1515 (6) | 0.3363 (2) | 0.0518 (14) | |
H37A | 0.1450 | −0.2052 | 0.3220 | 0.062* | |
H37B | 0.0709 | −0.1774 | 0.3065 | 0.062* | |
C38 | 0.1269 (2) | 0.0090 (5) | 0.3337 (2) | 0.0418 (13) | |
H38 | 0.1746 | 0.0237 | 0.3545 | 0.050* | |
C39 | 0.0200 (3) | 0.3511 (6) | 0.1674 (3) | 0.0614 (16) | |
H39A | 0.0080 | 0.4050 | 0.1249 | 0.092* | |
H39B | 0.0045 | 0.3994 | 0.1976 | 0.092* | |
H39C | 0.0004 | 0.2583 | 0.1561 | 0.092* | |
C40 | 0.0263 (2) | 0.0573 (7) | 0.3583 (3) | 0.0608 (16) | |
H40A | 0.0116 | 0.1137 | 0.3867 | 0.091* | |
H40B | 0.0156 | −0.0408 | 0.3607 | 0.091* | |
H40C | 0.0050 | 0.0894 | 0.3103 | 0.091* | |
C41 | 0.1186 (3) | −0.0197 (7) | 0.5123 (3) | 0.0639 (17) | |
C42 | 0.1534 (4) | −0.1208 (7) | 0.5732 (3) | 0.109 (3) | |
H42A | 0.1837 | −0.0684 | 0.6133 | 0.163* | |
H42B | 0.1769 | −0.1910 | 0.5600 | 0.163* | |
H42C | 0.1215 | −0.1672 | 0.5850 | 0.163* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0707 (4) | 0.0954 (5) | 0.0834 (4) | −0.0043 (4) | 0.0609 (4) | −0.0067 (4) |
Br2 | 0.1102 (6) | 0.0655 (5) | 0.0911 (5) | −0.0367 (4) | 0.0319 (4) | 0.0002 (4) |
O1 | 0.054 (3) | 0.084 (3) | 0.084 (3) | 0.005 (2) | 0.038 (2) | 0.035 (3) |
O2 | 0.080 (3) | 0.051 (3) | 0.052 (2) | −0.019 (2) | 0.012 (2) | 0.000 (2) |
O3 | 0.035 (2) | 0.060 (3) | 0.0365 (18) | 0.0079 (18) | 0.0140 (16) | 0.0032 (17) |
O4 | 0.063 (3) | 0.072 (3) | 0.063 (2) | 0.005 (2) | 0.042 (2) | 0.009 (2) |
O5 | 0.091 (4) | 0.111 (4) | 0.081 (3) | −0.004 (3) | 0.058 (3) | −0.004 (3) |
O6 | 0.057 (3) | 0.060 (3) | 0.048 (2) | −0.0077 (19) | 0.015 (2) | −0.0104 (19) |
C1 | 0.060 (4) | 0.048 (4) | 0.044 (3) | 0.005 (3) | 0.028 (3) | 0.009 (3) |
C2 | 0.069 (4) | 0.076 (5) | 0.056 (4) | 0.017 (4) | 0.042 (3) | 0.019 (3) |
C3 | 0.048 (3) | 0.060 (4) | 0.061 (3) | 0.006 (3) | 0.023 (3) | 0.021 (4) |
C4 | 0.058 (4) | 0.056 (4) | 0.048 (3) | −0.011 (3) | 0.019 (3) | 0.008 (3) |
C5 | 0.047 (3) | 0.032 (3) | 0.043 (3) | −0.001 (3) | 0.014 (3) | 0.001 (2) |
C6 | 0.086 (4) | 0.031 (3) | 0.065 (3) | −0.001 (3) | 0.044 (3) | −0.006 (3) |
C7 | 0.086 (4) | 0.031 (3) | 0.061 (3) | −0.006 (3) | 0.044 (3) | −0.016 (3) |
C8 | 0.045 (3) | 0.035 (3) | 0.038 (3) | 0.006 (3) | 0.020 (3) | 0.002 (3) |
C9 | 0.040 (3) | 0.038 (3) | 0.030 (3) | −0.001 (2) | 0.017 (2) | −0.006 (2) |
C10 | 0.036 (3) | 0.041 (3) | 0.033 (3) | 0.001 (2) | 0.017 (3) | 0.004 (2) |
C11 | 0.069 (4) | 0.046 (3) | 0.032 (2) | 0.007 (3) | 0.027 (3) | 0.003 (3) |
C12 | 0.067 (4) | 0.026 (3) | 0.032 (3) | −0.001 (2) | 0.025 (3) | −0.005 (2) |
C13 | 0.036 (3) | 0.037 (3) | 0.026 (2) | 0.004 (3) | 0.010 (2) | 0.003 (3) |
C14 | 0.026 (3) | 0.048 (3) | 0.036 (3) | −0.001 (2) | 0.012 (2) | −0.004 (2) |
C15 | 0.036 (3) | 0.052 (4) | 0.032 (2) | −0.005 (3) | 0.016 (2) | −0.003 (2) |
C16 | 0.051 (4) | 0.041 (4) | 0.039 (3) | 0.001 (3) | 0.021 (3) | −0.009 (3) |
C17 | 0.036 (3) | 0.045 (3) | 0.030 (3) | 0.005 (3) | 0.018 (2) | −0.005 (2) |
C18 | 0.050 (4) | 0.057 (4) | 0.057 (3) | 0.004 (3) | 0.013 (3) | 0.010 (3) |
C19 | 0.040 (3) | 0.053 (4) | 0.046 (3) | −0.002 (3) | 0.008 (2) | −0.003 (3) |
C20 | 0.044 (4) | 0.053 (4) | 0.040 (3) | 0.013 (3) | 0.022 (3) | 0.007 (3) |
C21 | 0.083 (5) | 0.063 (4) | 0.055 (3) | −0.006 (3) | 0.027 (3) | 0.008 (3) |
C22 | 0.063 (4) | 0.048 (4) | 0.059 (3) | 0.002 (3) | 0.036 (3) | −0.008 (3) |
C23 | 0.063 (4) | 0.057 (4) | 0.058 (3) | 0.008 (3) | 0.035 (3) | 0.002 (3) |
C24 | 0.046 (4) | 0.053 (4) | 0.040 (3) | 0.007 (3) | 0.022 (3) | −0.001 (3) |
C25 | 0.062 (4) | 0.061 (4) | 0.044 (3) | 0.007 (3) | 0.033 (3) | −0.006 (3) |
C26 | 0.046 (3) | 0.048 (3) | 0.039 (3) | 0.006 (3) | 0.018 (2) | −0.011 (3) |
C27 | 0.064 (4) | 0.067 (5) | 0.050 (3) | 0.001 (3) | 0.027 (3) | −0.013 (3) |
C28 | 0.067 (4) | 0.043 (4) | 0.046 (3) | −0.003 (3) | 0.023 (3) | −0.016 (3) |
C29 | 0.042 (3) | 0.041 (3) | 0.042 (3) | 0.003 (3) | 0.018 (3) | −0.008 (3) |
C30 | 0.045 (3) | 0.042 (3) | 0.041 (3) | 0.008 (3) | 0.024 (2) | −0.002 (3) |
C31 | 0.048 (4) | 0.043 (4) | 0.044 (3) | 0.005 (3) | 0.024 (3) | −0.005 (3) |
C32 | 0.083 (4) | 0.044 (4) | 0.057 (3) | 0.004 (3) | 0.045 (3) | −0.006 (3) |
C33 | 0.080 (4) | 0.045 (4) | 0.056 (3) | 0.002 (3) | 0.044 (3) | −0.005 (3) |
C34 | 0.049 (4) | 0.043 (4) | 0.044 (3) | 0.003 (3) | 0.022 (3) | −0.002 (3) |
C35 | 0.037 (3) | 0.046 (4) | 0.050 (3) | −0.010 (3) | 0.015 (3) | −0.008 (3) |
C36 | 0.046 (4) | 0.049 (4) | 0.060 (3) | −0.003 (3) | 0.010 (3) | 0.004 (3) |
C37 | 0.054 (4) | 0.038 (3) | 0.053 (3) | −0.002 (3) | 0.013 (3) | −0.006 (3) |
C38 | 0.031 (3) | 0.048 (4) | 0.043 (3) | 0.002 (2) | 0.013 (3) | −0.006 (3) |
C39 | 0.051 (4) | 0.069 (4) | 0.069 (4) | 0.019 (3) | 0.030 (3) | 0.021 (3) |
C40 | 0.042 (4) | 0.080 (5) | 0.064 (3) | 0.007 (3) | 0.026 (3) | 0.010 (3) |
C41 | 0.078 (5) | 0.058 (4) | 0.066 (4) | −0.019 (4) | 0.042 (4) | −0.007 (4) |
C42 | 0.191 (8) | 0.070 (6) | 0.058 (4) | −0.016 (5) | 0.047 (5) | 0.015 (4) |
Br1—C15 | 1.984 (4) | C19—H19C | 0.9600 |
Br2—C36 | 1.976 (5) | C20—C21 | 1.523 (7) |
O1—C3 | 1.231 (6) | C21—H21A | 0.9600 |
O2—C20 | 1.204 (5) | C21—H21B | 0.9600 |
O3—C14 | 1.463 (5) | C21—H21C | 0.9600 |
O3—H3 | 0.8200 | C22—C23 | 1.524 (7) |
O4—C24 | 1.231 (6) | C22—C31 | 1.530 (7) |
O5—C41 | 1.206 (7) | C22—H22A | 0.9700 |
O6—C35 | 1.456 (5) | C22—H22B | 0.9700 |
O6—H6 | 0.8200 | C23—C24 | 1.498 (7) |
C1—C2 | 1.540 (7) | C23—H23A | 0.9700 |
C1—C10 | 1.547 (6) | C23—H23B | 0.9700 |
C1—H1A | 0.9700 | C24—C25 | 1.460 (7) |
C1—H1B | 0.9700 | C25—C26 | 1.344 (6) |
C2—C3 | 1.480 (8) | C25—H25 | 0.9300 |
C2—H2A | 0.9700 | C26—C27 | 1.505 (7) |
C2—H2B | 0.9700 | C26—C31 | 1.528 (6) |
C3—C4 | 1.464 (6) | C27—C28 | 1.549 (7) |
C4—C5 | 1.333 (6) | C27—H27A | 0.9700 |
C4—H4 | 0.9300 | C27—H27B | 0.9700 |
C5—C10 | 1.510 (6) | C28—C29 | 1.513 (6) |
C5—C6 | 1.522 (6) | C28—H28A | 0.9700 |
C6—C7 | 1.509 (7) | C28—H28B | 0.9700 |
C6—H6A | 0.9700 | C29—C38 | 1.538 (6) |
C6—H6B | 0.9700 | C29—C30 | 1.542 (7) |
C7—C8 | 1.524 (7) | C29—H29 | 0.9800 |
C7—H7A | 0.9700 | C30—C32 | 1.540 (6) |
C7—H7B | 0.9700 | C30—C31 | 1.570 (6) |
C8—C17 | 1.516 (6) | C30—H30 | 0.9800 |
C8—C9 | 1.561 (6) | C31—C39 | 1.543 (7) |
C8—H8 | 0.9800 | C32—C33 | 1.548 (6) |
C9—C11 | 1.532 (7) | C32—H32A | 0.9700 |
C9—C10 | 1.569 (6) | C32—H32B | 0.9700 |
C9—H9 | 0.9800 | C33—C34 | 1.525 (7) |
C10—C18 | 1.554 (7) | C33—H33A | 0.9700 |
C11—C12 | 1.539 (6) | C33—H33B | 0.9700 |
C11—H11A | 0.9700 | C34—C38 | 1.554 (6) |
C11—H11B | 0.9700 | C34—C35 | 1.560 (7) |
C12—C13 | 1.542 (5) | C34—C40 | 1.568 (7) |
C12—H12A | 0.9700 | C35—C36 | 1.537 (7) |
C12—H12B | 0.9700 | C35—C41 | 1.571 (7) |
C13—C17 | 1.540 (7) | C36—C37 | 1.554 (6) |
C13—C14 | 1.557 (6) | C36—H36 | 0.9800 |
C13—C19 | 1.561 (6) | C37—C38 | 1.531 (7) |
C14—C20 | 1.544 (7) | C37—H37A | 0.9700 |
C14—C15 | 1.559 (6) | C37—H37B | 0.9700 |
C15—C16 | 1.546 (7) | C38—H38 | 0.9800 |
C15—H15 | 0.9800 | C39—H39A | 0.9600 |
C16—C17 | 1.543 (6) | C39—H39B | 0.9600 |
C16—H16A | 0.9700 | C39—H39C | 0.9600 |
C16—H16B | 0.9700 | C40—H40A | 0.9600 |
C17—H17 | 0.9800 | C40—H40B | 0.9600 |
C18—H18A | 0.9600 | C40—H40C | 0.9600 |
C18—H18B | 0.9600 | C41—C42 | 1.514 (9) |
C18—H18C | 0.9600 | C42—H42A | 0.9600 |
C19—H19A | 0.9600 | C42—H42B | 0.9600 |
C19—H19B | 0.9600 | C42—H42C | 0.9600 |
C14—O3—H3 | 109.5 | H21B—C21—H21C | 109.5 |
C35—O6—H6 | 109.5 | C23—C22—C31 | 115.1 (4) |
C2—C1—C10 | 113.2 (4) | C23—C22—H22A | 108.5 |
C2—C1—H1A | 108.9 | C31—C22—H22A | 108.5 |
C10—C1—H1A | 108.9 | C23—C22—H22B | 108.5 |
C2—C1—H1B | 108.9 | C31—C22—H22B | 108.5 |
C10—C1—H1B | 108.9 | H22A—C22—H22B | 107.5 |
H1A—C1—H1B | 107.8 | C24—C23—C22 | 110.1 (4) |
C3—C2—C1 | 112.2 (4) | C24—C23—H23A | 109.6 |
C3—C2—H2A | 109.2 | C22—C23—H23A | 109.6 |
C1—C2—H2A | 109.2 | C24—C23—H23B | 109.6 |
C3—C2—H2B | 109.2 | C22—C23—H23B | 109.6 |
C1—C2—H2B | 109.2 | H23A—C23—H23B | 108.2 |
H2A—C2—H2B | 107.9 | O4—C24—C25 | 122.3 (5) |
O1—C3—C4 | 121.0 (6) | O4—C24—C23 | 122.1 (5) |
O1—C3—C2 | 122.7 (5) | C25—C24—C23 | 115.7 (5) |
C4—C3—C2 | 116.2 (5) | C26—C25—C24 | 123.9 (5) |
C5—C4—C3 | 124.0 (5) | C26—C25—H25 | 118.1 |
C5—C4—H4 | 118.0 | C24—C25—H25 | 118.1 |
C3—C4—H4 | 118.0 | C25—C26—C27 | 120.8 (4) |
C4—C5—C10 | 123.4 (4) | C25—C26—C31 | 123.0 (5) |
C4—C5—C6 | 119.5 (5) | C27—C26—C31 | 116.2 (4) |
C10—C5—C6 | 117.1 (4) | C26—C27—C28 | 113.0 (4) |
C7—C6—C5 | 111.4 (4) | C26—C27—H27A | 109.0 |
C7—C6—H6A | 109.4 | C28—C27—H27A | 109.0 |
C5—C6—H6A | 109.4 | C26—C27—H27B | 109.0 |
C7—C6—H6B | 109.4 | C28—C27—H27B | 109.0 |
C5—C6—H6B | 109.4 | H27A—C27—H27B | 107.8 |
H6A—C6—H6B | 108.0 | C29—C28—C27 | 110.8 (5) |
C6—C7—C8 | 113.4 (4) | C29—C28—H28A | 109.5 |
C6—C7—H7A | 108.9 | C27—C28—H28A | 109.5 |
C8—C7—H7A | 108.9 | C29—C28—H28B | 109.5 |
C6—C7—H7B | 108.9 | C27—C28—H28B | 109.5 |
C8—C7—H7B | 108.9 | H28A—C28—H28B | 108.1 |
H7A—C7—H7B | 107.7 | C28—C29—C38 | 110.4 (4) |
C17—C8—C7 | 113.8 (4) | C28—C29—C30 | 111.5 (4) |
C17—C8—C9 | 108.9 (4) | C38—C29—C30 | 108.7 (4) |
C7—C8—C9 | 108.7 (4) | C28—C29—H29 | 108.7 |
C17—C8—H8 | 108.4 | C38—C29—H29 | 108.7 |
C7—C8—H8 | 108.4 | C30—C29—H29 | 108.7 |
C9—C8—H8 | 108.4 | C32—C30—C29 | 111.5 (4) |
C11—C9—C8 | 112.6 (4) | C32—C30—C31 | 111.7 (4) |
C11—C9—C10 | 113.2 (3) | C29—C30—C31 | 114.9 (4) |
C8—C9—C10 | 112.4 (4) | C32—C30—H30 | 106.0 |
C11—C9—H9 | 106.0 | C29—C30—H30 | 106.0 |
C8—C9—H9 | 106.0 | C31—C30—H30 | 106.0 |
C10—C9—H9 | 106.0 | C26—C31—C22 | 109.9 (4) |
C5—C10—C1 | 109.8 (4) | C26—C31—C39 | 108.5 (4) |
C5—C10—C18 | 108.2 (4) | C22—C31—C39 | 110.4 (4) |
C1—C10—C18 | 109.5 (4) | C26—C31—C30 | 107.0 (4) |
C5—C10—C9 | 109.2 (4) | C22—C31—C30 | 109.2 (4) |
C1—C10—C9 | 108.2 (4) | C39—C31—C30 | 111.9 (4) |
C18—C10—C9 | 111.9 (4) | C30—C32—C33 | 112.9 (4) |
C9—C11—C12 | 114.6 (3) | C30—C32—H32A | 109.0 |
C9—C11—H11A | 108.6 | C33—C32—H32A | 109.0 |
C12—C11—H11A | 108.6 | C30—C32—H32B | 109.0 |
C9—C11—H11B | 108.6 | C33—C32—H32B | 109.0 |
C12—C11—H11B | 108.6 | H32A—C32—H32B | 107.8 |
H11A—C11—H11B | 107.6 | C34—C33—C32 | 111.1 (4) |
C11—C12—C13 | 110.4 (4) | C34—C33—H33A | 109.4 |
C11—C12—H12A | 109.6 | C32—C33—H33A | 109.4 |
C13—C12—H12A | 109.6 | C34—C33—H33B | 109.4 |
C11—C12—H12B | 109.6 | C32—C33—H33B | 109.4 |
C13—C12—H12B | 109.6 | H33A—C33—H33B | 108.0 |
H12A—C12—H12B | 108.1 | C33—C34—C38 | 109.0 (4) |
C17—C13—C12 | 108.2 (3) | C33—C34—C35 | 116.6 (4) |
C17—C13—C14 | 100.7 (3) | C38—C34—C35 | 99.0 (4) |
C12—C13—C14 | 116.8 (4) | C33—C34—C40 | 110.4 (4) |
C17—C13—C19 | 110.8 (4) | C38—C34—C40 | 111.4 (4) |
C12—C13—C19 | 109.7 (3) | C35—C34—C40 | 110.0 (4) |
C14—C13—C19 | 110.2 (3) | O6—C35—C36 | 102.4 (4) |
O3—C14—C20 | 105.7 (4) | O6—C35—C34 | 110.8 (4) |
O3—C14—C13 | 111.5 (3) | C36—C35—C34 | 104.5 (4) |
C20—C14—C13 | 117.8 (4) | O6—C35—C41 | 104.3 (4) |
O3—C14—C15 | 101.0 (3) | C36—C35—C41 | 117.2 (4) |
C20—C14—C15 | 116.8 (4) | C34—C35—C41 | 116.7 (4) |
C13—C14—C15 | 102.9 (4) | C35—C36—C37 | 107.3 (4) |
C16—C15—C14 | 107.1 (3) | C35—C36—Br2 | 116.8 (4) |
C16—C15—Br1 | 111.4 (3) | C37—C36—Br2 | 109.3 (3) |
C14—C15—Br1 | 113.6 (3) | C35—C36—H36 | 107.7 |
C16—C15—H15 | 108.2 | C37—C36—H36 | 107.7 |
C14—C15—H15 | 108.2 | Br2—C36—H36 | 107.7 |
Br1—C15—H15 | 108.2 | C38—C37—C36 | 102.6 (4) |
C17—C16—C15 | 103.9 (4) | C38—C37—H37A | 111.2 |
C17—C16—H16A | 111.0 | C36—C37—H37A | 111.2 |
C15—C16—H16A | 111.0 | C38—C37—H37B | 111.2 |
C17—C16—H16B | 111.0 | C36—C37—H37B | 111.2 |
C15—C16—H16B | 111.0 | H37A—C37—H37B | 109.2 |
H16A—C16—H16B | 109.0 | C37—C38—C29 | 119.5 (4) |
C8—C17—C13 | 115.2 (3) | C37—C38—C34 | 104.2 (4) |
C8—C17—C16 | 117.8 (4) | C29—C38—C34 | 113.0 (4) |
C13—C17—C16 | 103.5 (4) | C37—C38—H38 | 106.4 |
C8—C17—H17 | 106.5 | C29—C38—H38 | 106.4 |
C13—C17—H17 | 106.5 | C34—C38—H38 | 106.4 |
C16—C17—H17 | 106.5 | C31—C39—H39A | 109.5 |
C10—C18—H18A | 109.5 | C31—C39—H39B | 109.5 |
C10—C18—H18B | 109.5 | H39A—C39—H39B | 109.5 |
H18A—C18—H18B | 109.5 | C31—C39—H39C | 109.5 |
C10—C18—H18C | 109.5 | H39A—C39—H39C | 109.5 |
H18A—C18—H18C | 109.5 | H39B—C39—H39C | 109.5 |
H18B—C18—H18C | 109.5 | C34—C40—H40A | 109.5 |
C13—C19—H19A | 109.5 | C34—C40—H40B | 109.5 |
C13—C19—H19B | 109.5 | H40A—C40—H40B | 109.5 |
H19A—C19—H19B | 109.5 | C34—C40—H40C | 109.5 |
C13—C19—H19C | 109.5 | H40A—C40—H40C | 109.5 |
H19A—C19—H19C | 109.5 | H40B—C40—H40C | 109.5 |
H19B—C19—H19C | 109.5 | O5—C41—C42 | 122.6 (6) |
O2—C20—C21 | 120.6 (5) | O5—C41—C35 | 120.6 (6) |
O2—C20—C14 | 122.8 (4) | C42—C41—C35 | 116.3 (6) |
C21—C20—C14 | 116.4 (5) | C41—C42—H42A | 109.5 |
C20—C21—H21A | 109.5 | C41—C42—H42B | 109.5 |
C20—C21—H21B | 109.5 | H42A—C42—H42B | 109.5 |
H21A—C21—H21B | 109.5 | C41—C42—H42C | 109.5 |
C20—C21—H21C | 109.5 | H42A—C42—H42C | 109.5 |
H21A—C21—H21C | 109.5 | H42B—C42—H42C | 109.5 |
C10—C1—C2—C3 | −53.5 (6) | C31—C22—C23—C24 | −56.3 (6) |
C1—C2—C3—O1 | −152.0 (5) | C22—C23—C24—O4 | −141.4 (5) |
C1—C2—C3—C4 | 30.9 (7) | C22—C23—C24—C25 | 38.3 (6) |
O1—C3—C4—C5 | −178.1 (5) | O4—C24—C25—C26 | 171.1 (5) |
C2—C3—C4—C5 | −0.9 (8) | C23—C24—C25—C26 | −8.6 (7) |
C3—C4—C5—C10 | −7.5 (8) | C24—C25—C26—C27 | 174.4 (5) |
C3—C4—C5—C6 | 170.3 (5) | C24—C25—C26—C31 | −6.7 (8) |
C4—C5—C6—C7 | 132.8 (5) | C25—C26—C27—C28 | 125.7 (5) |
C10—C5—C6—C7 | −49.3 (6) | C31—C26—C27—C28 | −53.3 (6) |
C5—C6—C7—C8 | 52.6 (6) | C26—C27—C28—C29 | 51.9 (6) |
C6—C7—C8—C17 | −178.8 (4) | C27—C28—C29—C38 | −173.5 (5) |
C6—C7—C8—C9 | −57.2 (5) | C27—C28—C29—C30 | −52.5 (6) |
C17—C8—C9—C11 | −49.1 (5) | C28—C29—C30—C32 | −176.4 (4) |
C7—C8—C9—C11 | −173.6 (4) | C38—C29—C30—C32 | −54.5 (5) |
C17—C8—C9—C10 | −178.3 (4) | C28—C29—C30—C31 | 55.2 (5) |
C7—C8—C9—C10 | 57.2 (5) | C38—C29—C30—C31 | 177.1 (4) |
C4—C5—C10—C1 | −14.8 (6) | C25—C26—C31—C22 | −9.8 (7) |
C6—C5—C10—C1 | 167.3 (4) | C27—C26—C31—C22 | 169.1 (4) |
C4—C5—C10—C18 | 104.7 (5) | C25—C26—C31—C39 | 111.0 (5) |
C6—C5—C10—C18 | −73.2 (5) | C27—C26—C31—C39 | −70.1 (6) |
C4—C5—C10—C9 | −133.3 (5) | C25—C26—C31—C30 | −128.2 (5) |
C6—C5—C10—C9 | 48.8 (5) | C27—C26—C31—C30 | 50.8 (6) |
C2—C1—C10—C5 | 44.3 (6) | C23—C22—C31—C26 | 41.3 (6) |
C2—C1—C10—C18 | −74.5 (6) | C23—C22—C31—C39 | −78.3 (5) |
C2—C1—C10—C9 | 163.4 (4) | C23—C22—C31—C30 | 158.3 (4) |
C11—C9—C10—C5 | 178.6 (4) | C32—C30—C31—C26 | −179.8 (4) |
C8—C9—C10—C5 | −52.5 (5) | C29—C30—C31—C26 | −51.5 (5) |
C11—C9—C10—C1 | 59.1 (5) | C32—C30—C31—C22 | 61.3 (5) |
C8—C9—C10—C1 | −172.0 (4) | C29—C30—C31—C22 | −170.4 (4) |
C11—C9—C10—C18 | −61.6 (5) | C32—C30—C31—C39 | −61.2 (6) |
C8—C9—C10—C18 | 67.3 (5) | C29—C30—C31—C39 | 67.2 (5) |
C8—C9—C11—C12 | 50.3 (6) | C29—C30—C32—C33 | 53.9 (6) |
C10—C9—C11—C12 | 179.1 (4) | C31—C30—C32—C33 | −175.9 (4) |
C9—C11—C12—C13 | −53.5 (5) | C30—C32—C33—C34 | −54.3 (6) |
C11—C12—C13—C17 | 55.4 (5) | C32—C33—C34—C38 | 55.0 (5) |
C11—C12—C13—C14 | 168.1 (4) | C32—C33—C34—C35 | 165.9 (4) |
C11—C12—C13—C19 | −65.7 (5) | C32—C33—C34—C40 | −67.6 (5) |
C17—C13—C14—O3 | 66.8 (4) | C33—C34—C35—O6 | −45.9 (5) |
C12—C13—C14—O3 | −50.1 (5) | C38—C34—C35—O6 | 70.7 (5) |
C19—C13—C14—O3 | −176.1 (4) | C40—C34—C35—O6 | −172.6 (4) |
C17—C13—C14—C20 | −170.8 (4) | C33—C34—C35—C36 | −155.5 (4) |
C12—C13—C14—C20 | 72.3 (5) | C38—C34—C35—C36 | −38.9 (5) |
C19—C13—C14—C20 | −53.7 (5) | C40—C34—C35—C36 | 77.8 (5) |
C17—C13—C14—C15 | −40.7 (4) | C33—C34—C35—C41 | 73.3 (6) |
C12—C13—C14—C15 | −157.6 (4) | C38—C34—C35—C41 | −170.1 (4) |
C19—C13—C14—C15 | 76.4 (5) | C40—C34—C35—C41 | −53.4 (6) |
O3—C14—C15—C16 | −94.9 (4) | O6—C35—C36—C37 | −98.2 (4) |
C20—C14—C15—C16 | 151.1 (4) | C34—C35—C36—C37 | 17.4 (5) |
C13—C14—C15—C16 | 20.4 (4) | C41—C35—C36—C37 | 148.3 (5) |
O3—C14—C15—Br1 | 141.6 (3) | O6—C35—C36—Br2 | 138.7 (3) |
C20—C14—C15—Br1 | 27.6 (5) | C34—C35—C36—Br2 | −105.7 (4) |
C13—C14—C15—Br1 | −103.1 (3) | C41—C35—C36—Br2 | 25.2 (6) |
C14—C15—C16—C17 | 8.0 (5) | C35—C36—C37—C38 | 11.9 (5) |
Br1—C15—C16—C17 | 132.8 (3) | Br2—C36—C37—C38 | 139.5 (4) |
C7—C8—C17—C13 | 177.6 (4) | C36—C37—C38—C29 | −164.4 (4) |
C9—C8—C17—C13 | 56.1 (5) | C36—C37—C38—C34 | −37.2 (5) |
C7—C8—C17—C16 | −59.6 (6) | C28—C29—C38—C37 | −55.9 (6) |
C9—C8—C17—C16 | 178.9 (4) | C30—C29—C38—C37 | −178.6 (4) |
C12—C13—C17—C8 | −60.1 (5) | C28—C29—C38—C34 | −179.0 (4) |
C14—C13—C17—C8 | 176.8 (4) | C30—C29—C38—C34 | 58.3 (5) |
C19—C13—C17—C8 | 60.2 (5) | C33—C34—C38—C37 | 169.7 (4) |
C12—C13—C17—C16 | 169.8 (4) | C35—C34—C38—C37 | 47.4 (5) |
C14—C13—C17—C16 | 46.7 (4) | C40—C34—C38—C37 | −68.2 (5) |
C19—C13—C17—C16 | −69.9 (4) | C33—C34—C38—C29 | −59.1 (6) |
C15—C16—C17—C8 | −162.5 (4) | C35—C34—C38—C29 | 178.7 (4) |
C15—C16—C17—C13 | −33.9 (5) | C40—C34—C38—C29 | 63.0 (5) |
O3—C14—C20—O2 | 125.3 (5) | O6—C35—C41—O5 | 114.6 (6) |
C13—C14—C20—O2 | −0.1 (7) | C36—C35—C41—O5 | −133.1 (6) |
C15—C14—C20—O2 | −123.4 (5) | C34—C35—C41—O5 | −8.0 (8) |
O3—C14—C20—C21 | −50.1 (5) | O6—C35—C41—C42 | −57.9 (6) |
C13—C14—C20—C21 | −175.5 (4) | C36—C35—C41—C42 | 54.5 (7) |
C15—C14—C20—C21 | 61.2 (6) | C34—C35—C41—C42 | 179.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O1i | 0.82 | 2.04 | 2.836 (5) | 163 |
O3—H3···O4 | 0.82 | 2.02 | 2.798 (5) | 158 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1. |