Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023268/wn6283sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023268/wn6283Isup2.hkl |
CCDC reference: 253027
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C34H30Br2O2·C3H6O | Z = 2 |
Mr = 688.48 | F(000) = 704 |
Triclinic, P1 | Dx = 1.419 Mg m−3 |
Hall symbol: -P 1 | Melting point = 428–429 K |
a = 11.427 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.042 (1) Å | Cell parameters from 27 reflections |
c = 12.992 (2) Å | θ = 3.0–15.1° |
α = 77.87 (1)° | µ = 2.55 mm−1 |
β = 67.73 (1)° | T = 296 K |
γ = 81.02 (1)° | Block, colorless |
V = 1611.8 (4) Å3 | 0.36 × 0.36 × 0.14 mm |
Siemens P4 diffractometer | 2436 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.3°, θmin = 1.7° |
ω scans | h = 0→13 |
Absorption correction: ψ scan (XSCANS; Siemens, 1994) | k = −14→14 |
Tmin = 0.446, Tmax = 0.700 | l = −14→15 |
6445 measured reflections | 3 standard reflections every 97 reflections |
5836 independent reflections | intensity decay: 7.0% |
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)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.045 | w = 1/[σ2(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max = 0.001 |
5836 reflections | Δρmax = 0.36 e Å−3 |
390 parameters | Δρmin = −0.30 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0067 (2) |
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 | 0.46259 (3) | 0.71697 (3) | 0.38617 (4) | 0.07577 (17) | |
Br2 | 0.61361 (4) | −0.02315 (4) | 0.33515 (4) | 0.0967 (2) | |
O1 | 1.2488 (2) | 0.3894 (2) | 0.0665 (2) | 0.0493 (7) | |
O2 | 1.1133 (2) | 0.5865 (2) | 0.0305 (2) | 0.0496 (7) | |
C1 | 0.9807 (3) | 0.4336 (2) | 0.2298 (2) | 0.0324 (8) | |
H1 | 0.9927 | 0.4222 | 0.1539 | 0.039* | |
C2 | 0.9894 (2) | 0.3141 (2) | 0.2992 (2) | 0.0335 (8) | |
H2 | 0.9795 | 0.3227 | 0.3755 | 0.040* | |
C3 | 1.1276 (3) | 0.2693 (3) | 0.2390 (2) | 0.0391 (9) | |
H3 | 1.1284 | 0.2372 | 0.1753 | 0.047* | |
C4 | 1.2046 (3) | 0.3764 (3) | 0.1878 (3) | 0.0374 (9) | |
C5 | 1.1038 (3) | 0.4809 (2) | 0.2206 (2) | 0.0292 (8) | |
C6 | 1.1798 (3) | 0.1737 (3) | 0.3119 (3) | 0.0573 (11) | |
H6A | 1.2497 | 0.1297 | 0.2635 | 0.069* | |
H6B | 1.1140 | 0.1231 | 0.3572 | 0.069* | |
C7 | 1.2260 (3) | 0.2200 (3) | 0.3896 (3) | 0.0596 (11) | |
H7A | 1.1557 | 0.2604 | 0.4413 | 0.072* | |
H7B | 1.2601 | 0.1574 | 0.4335 | 0.072* | |
C8 | 1.3269 (3) | 0.2992 (3) | 0.3194 (3) | 0.0471 (10) | |
C9 | 1.4324 (3) | 0.2983 (3) | 0.3491 (3) | 0.0599 (11) | |
H9 | 1.4381 | 0.2501 | 0.4134 | 0.072* | |
C10 | 1.5283 (3) | 0.3678 (3) | 0.2846 (3) | 0.0652 (13) | |
H10 | 1.5975 | 0.3673 | 0.3059 | 0.078* | |
C11 | 1.5210 (3) | 0.4376 (3) | 0.1886 (3) | 0.0642 (12) | |
H11 | 1.5856 | 0.4844 | 0.1445 | 0.077* | |
C12 | 1.4177 (3) | 0.4383 (3) | 0.1576 (3) | 0.0539 (10) | |
H12 | 1.4143 | 0.4851 | 0.0918 | 0.065* | |
C13 | 1.3187 (3) | 0.3706 (3) | 0.2228 (3) | 0.0384 (9) | |
C14 | 1.0911 (2) | 0.5099 (2) | 0.3357 (2) | 0.0390 (9) | |
H14A | 1.0016 | 0.5219 | 0.3801 | 0.047* | |
H14B | 1.1264 | 0.4446 | 0.3759 | 0.047* | |
C15 | 1.1562 (3) | 0.6145 (3) | 0.3275 (2) | 0.0476 (9) | |
H15A | 1.1426 | 0.6276 | 0.4025 | 0.057* | |
H15B | 1.2468 | 0.6022 | 0.2876 | 0.057* | |
C16 | 1.1022 (3) | 0.7165 (3) | 0.2657 (3) | 0.0433 (9) | |
C17 | 1.0635 (3) | 0.8197 (3) | 0.3030 (3) | 0.0590 (11) | |
H17 | 1.0725 | 0.8292 | 0.3687 | 0.071* | |
C18 | 1.0117 (3) | 0.9087 (3) | 0.2443 (3) | 0.0674 (12) | |
H18 | 0.9873 | 0.9788 | 0.2690 | 0.081* | |
C19 | 0.9963 (3) | 0.8934 (3) | 0.1489 (3) | 0.0633 (12) | |
H19 | 0.9602 | 0.9532 | 0.1094 | 0.076* | |
C20 | 1.0337 (3) | 0.7900 (3) | 0.1102 (3) | 0.0520 (10) | |
H20 | 1.0230 | 0.7809 | 0.0450 | 0.062* | |
C21 | 1.0869 (3) | 0.7005 (3) | 0.1684 (3) | 0.0360 (9) | |
C22 | 1.1408 (3) | 0.5887 (3) | 0.1282 (3) | 0.0403 (9) | |
H22 | 1.2333 | 0.5884 | 0.1031 | 0.048* | |
C23 | 0.8554 (3) | 0.5052 (3) | 0.2707 (3) | 0.0327 (8) | |
C24 | 0.8161 (3) | 0.5863 (3) | 0.1954 (3) | 0.0433 (10) | |
H24 | 0.8691 | 0.5979 | 0.1200 | 0.052* | |
C25 | 0.7010 (3) | 0.6507 (3) | 0.2280 (3) | 0.0496 (10) | |
H25 | 0.6768 | 0.7048 | 0.1755 | 0.059* | |
C26 | 0.6234 (3) | 0.6336 (3) | 0.3389 (3) | 0.0443 (10) | |
C27 | 0.6591 (3) | 0.5551 (3) | 0.4165 (3) | 0.0461 (10) | |
H27 | 0.6058 | 0.5449 | 0.4919 | 0.055* | |
C28 | 0.7741 (3) | 0.4909 (2) | 0.3836 (3) | 0.0445 (9) | |
H28 | 0.7977 | 0.4376 | 0.4369 | 0.053* | |
C29 | 0.8927 (3) | 0.2359 (3) | 0.3083 (3) | 0.0358 (9) | |
C30 | 0.8677 (3) | 0.2243 (3) | 0.2160 (3) | 0.0453 (10) | |
H30 | 0.9080 | 0.2681 | 0.1466 | 0.054* | |
C31 | 0.7833 (3) | 0.1483 (3) | 0.2237 (3) | 0.0518 (10) | |
H31 | 0.7683 | 0.1410 | 0.1600 | 0.062* | |
C32 | 0.7221 (3) | 0.0840 (3) | 0.3267 (4) | 0.0512 (11) | |
C33 | 0.7428 (3) | 0.0961 (3) | 0.4192 (3) | 0.0605 (11) | |
H33 | 0.6999 | 0.0540 | 0.4888 | 0.073* | |
C34 | 0.8275 (3) | 0.1707 (3) | 0.4109 (3) | 0.0498 (10) | |
H34 | 0.8414 | 0.1774 | 0.4754 | 0.060* | |
O3 | 1.4162 (3) | 0.2020 (2) | −0.0190 (2) | 0.1159 (12) | |
C35 | 1.5981 (4) | 0.0979 (3) | −0.1286 (3) | 0.1331 (18) | |
H35A | 1.6391 | 0.0309 | −0.0975 | 0.160* | |
H35B | 1.6609 | 0.1414 | −0.1888 | 0.160* | |
H35C | 1.5405 | 0.0759 | −0.1571 | 0.160* | |
C36 | 1.5252 (5) | 0.1697 (4) | −0.0374 (4) | 0.0829 (15) | |
C37 | 1.5946 (4) | 0.1815 (4) | 0.0315 (4) | 0.167 (2) | |
H37A | 1.5849 | 0.2596 | 0.0417 | 0.201* | |
H37B | 1.6829 | 0.1590 | −0.0050 | 0.201* | |
H37C | 1.5622 | 0.1339 | 0.1036 | 0.201* | |
H1O | 1.301 (2) | 0.3380 (19) | 0.043 (3) | 0.090 (16)* | |
H2O | 1.158 (2) | 0.5284 (16) | 0.014 (3) | 0.063 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0418 (3) | 0.0584 (3) | 0.1137 (4) | 0.0068 (2) | −0.0178 (2) | −0.0131 (3) |
Br2 | 0.0859 (3) | 0.0837 (4) | 0.1250 (4) | −0.0443 (3) | −0.0257 (3) | −0.0229 (3) |
O1 | 0.0498 (16) | 0.0529 (18) | 0.0386 (18) | 0.0080 (14) | −0.0099 (14) | −0.0143 (15) |
O2 | 0.0658 (17) | 0.0452 (18) | 0.0351 (17) | 0.0052 (15) | −0.0189 (14) | −0.0067 (14) |
C1 | 0.039 (2) | 0.033 (2) | 0.027 (2) | −0.0021 (17) | −0.0132 (18) | −0.0044 (18) |
C2 | 0.036 (2) | 0.035 (2) | 0.034 (2) | −0.0010 (17) | −0.0180 (18) | −0.0070 (18) |
C3 | 0.035 (2) | 0.036 (2) | 0.049 (2) | 0.0028 (17) | −0.0183 (19) | −0.0115 (19) |
C4 | 0.036 (2) | 0.042 (2) | 0.033 (2) | −0.0025 (18) | −0.0106 (19) | −0.0088 (19) |
C5 | 0.034 (2) | 0.030 (2) | 0.025 (2) | −0.0018 (16) | −0.0128 (17) | −0.0052 (18) |
C6 | 0.047 (2) | 0.040 (3) | 0.086 (3) | −0.0026 (19) | −0.025 (2) | −0.010 (2) |
C7 | 0.061 (3) | 0.044 (3) | 0.072 (3) | 0.001 (2) | −0.036 (2) | 0.013 (2) |
C8 | 0.043 (2) | 0.040 (3) | 0.061 (3) | 0.0042 (19) | −0.024 (2) | −0.009 (2) |
C9 | 0.056 (3) | 0.063 (3) | 0.071 (3) | 0.014 (2) | −0.037 (3) | −0.019 (2) |
C10 | 0.047 (3) | 0.083 (4) | 0.086 (4) | 0.007 (2) | −0.040 (3) | −0.036 (3) |
C11 | 0.038 (3) | 0.061 (3) | 0.095 (4) | −0.009 (2) | −0.018 (3) | −0.024 (3) |
C12 | 0.037 (2) | 0.056 (3) | 0.064 (3) | −0.002 (2) | −0.013 (2) | −0.012 (2) |
C13 | 0.034 (2) | 0.037 (2) | 0.046 (3) | 0.0007 (18) | −0.013 (2) | −0.015 (2) |
C14 | 0.038 (2) | 0.038 (2) | 0.041 (2) | −0.0012 (17) | −0.0169 (18) | −0.0022 (19) |
C15 | 0.054 (2) | 0.051 (3) | 0.048 (2) | −0.008 (2) | −0.023 (2) | −0.018 (2) |
C16 | 0.038 (2) | 0.039 (3) | 0.051 (3) | −0.0046 (19) | −0.013 (2) | −0.007 (2) |
C17 | 0.067 (3) | 0.048 (3) | 0.065 (3) | 0.005 (2) | −0.027 (2) | −0.017 (2) |
C18 | 0.084 (3) | 0.047 (3) | 0.075 (3) | 0.008 (2) | −0.030 (3) | −0.027 (3) |
C19 | 0.084 (3) | 0.037 (3) | 0.060 (3) | 0.015 (2) | −0.028 (3) | 0.001 (2) |
C20 | 0.062 (2) | 0.046 (3) | 0.042 (3) | −0.004 (2) | −0.014 (2) | −0.003 (2) |
C21 | 0.039 (2) | 0.032 (2) | 0.031 (2) | −0.0065 (18) | −0.0070 (19) | −0.001 (2) |
C22 | 0.042 (2) | 0.045 (3) | 0.036 (2) | −0.0012 (18) | −0.0165 (19) | −0.008 (2) |
C23 | 0.034 (2) | 0.025 (2) | 0.044 (2) | −0.0034 (17) | −0.018 (2) | −0.0087 (19) |
C24 | 0.041 (2) | 0.046 (3) | 0.039 (2) | −0.0092 (19) | −0.013 (2) | 0.001 (2) |
C25 | 0.043 (2) | 0.038 (2) | 0.070 (3) | 0.003 (2) | −0.031 (2) | 0.000 (2) |
C26 | 0.032 (2) | 0.041 (2) | 0.059 (3) | −0.0009 (18) | −0.013 (2) | −0.013 (2) |
C27 | 0.039 (2) | 0.052 (3) | 0.042 (3) | −0.0022 (19) | −0.010 (2) | −0.008 (2) |
C28 | 0.040 (2) | 0.050 (3) | 0.042 (3) | −0.001 (2) | −0.014 (2) | −0.007 (2) |
C29 | 0.035 (2) | 0.033 (2) | 0.036 (2) | 0.0036 (17) | −0.009 (2) | −0.012 (2) |
C30 | 0.047 (2) | 0.042 (2) | 0.046 (3) | −0.0083 (18) | −0.016 (2) | −0.005 (2) |
C31 | 0.056 (2) | 0.050 (3) | 0.064 (3) | −0.002 (2) | −0.036 (2) | −0.014 (2) |
C32 | 0.045 (2) | 0.043 (3) | 0.064 (3) | −0.0095 (19) | −0.013 (2) | −0.013 (2) |
C33 | 0.064 (3) | 0.052 (3) | 0.057 (3) | −0.018 (2) | −0.005 (2) | −0.012 (2) |
C34 | 0.060 (3) | 0.046 (3) | 0.041 (3) | −0.011 (2) | −0.013 (2) | −0.006 (2) |
O3 | 0.099 (2) | 0.123 (3) | 0.141 (3) | 0.056 (2) | −0.065 (2) | −0.061 (2) |
C35 | 0.110 (4) | 0.148 (5) | 0.120 (4) | 0.023 (3) | −0.030 (3) | −0.024 (4) |
C36 | 0.092 (4) | 0.065 (3) | 0.094 (4) | 0.022 (3) | −0.040 (4) | −0.028 (3) |
C37 | 0.103 (4) | 0.215 (6) | 0.235 (7) | 0.005 (4) | −0.076 (4) | −0.130 (5) |
Br1—C26 | 1.895 (3) | C16—C17 | 1.377 (4) |
Br2—C32 | 1.884 (3) | C16—C21 | 1.394 (4) |
O1—C4 | 1.442 (3) | C17—C18 | 1.371 (4) |
O1—H1O | 0.810 (10) | C17—H17 | 0.9300 |
O2—C22 | 1.425 (3) | C18—C19 | 1.369 (4) |
O2—H2O | 0.815 (10) | C18—H18 | 0.9300 |
C1—C23 | 1.518 (3) | C19—C20 | 1.386 (4) |
C1—C2 | 1.541 (3) | C19—H19 | 0.9300 |
C1—C5 | 1.553 (3) | C20—C21 | 1.380 (4) |
C1—H1 | 0.9800 | C20—H20 | 0.9300 |
C2—C29 | 1.516 (3) | C21—C22 | 1.503 (4) |
C2—C3 | 1.540 (3) | C22—H22 | 0.9800 |
C2—H2 | 0.9800 | C23—C24 | 1.381 (3) |
C3—C6 | 1.528 (3) | C23—C28 | 1.398 (3) |
C3—C4 | 1.558 (4) | C24—C25 | 1.382 (3) |
C3—H3 | 0.9800 | C24—H24 | 0.9300 |
C4—C13 | 1.524 (4) | C25—C26 | 1.368 (4) |
C4—C5 | 1.579 (3) | C25—H25 | 0.9300 |
C5—C14 | 1.555 (3) | C26—C27 | 1.367 (4) |
C5—C22 | 1.561 (3) | C27—C28 | 1.380 (3) |
C6—C7 | 1.530 (3) | C27—H27 | 0.9300 |
C6—H6A | 0.9700 | C28—H28 | 0.9300 |
C6—H6B | 0.9700 | C29—C30 | 1.373 (3) |
C7—C8 | 1.500 (4) | C29—C34 | 1.393 (3) |
C7—H7A | 0.9700 | C30—C31 | 1.393 (4) |
C7—H7B | 0.9700 | C30—H30 | 0.9300 |
C8—C13 | 1.390 (4) | C31—C32 | 1.380 (4) |
C8—C9 | 1.397 (4) | C31—H31 | 0.9300 |
C9—C10 | 1.377 (4) | C32—C33 | 1.349 (4) |
C9—H9 | 0.9300 | C33—C34 | 1.381 (4) |
C10—C11 | 1.372 (4) | C33—H33 | 0.9300 |
C10—H10 | 0.9300 | C34—H34 | 0.9300 |
C11—C12 | 1.383 (4) | O3—C36 | 1.193 (4) |
C11—H11 | 0.9300 | C35—C36 | 1.518 (5) |
C12—C13 | 1.390 (4) | C35—H35A | 0.9600 |
C12—H12 | 0.9300 | C35—H35B | 0.9600 |
C14—C15 | 1.526 (3) | C35—H35C | 0.9600 |
C14—H14A | 0.9700 | C36—C37 | 1.441 (5) |
C14—H14B | 0.9700 | C37—H37A | 0.9600 |
C15—C16 | 1.503 (4) | C37—H37B | 0.9600 |
C15—H15A | 0.9700 | C37—H37C | 0.9600 |
C15—H15B | 0.9700 | ||
C4—O1—H1O | 112 (2) | C17—C16—C15 | 123.5 (4) |
C22—O2—H2O | 96 (2) | C21—C16—C15 | 116.3 (3) |
C23—C1—C2 | 116.3 (2) | C18—C17—C16 | 120.7 (4) |
C23—C1—C5 | 118.8 (2) | C18—C17—H17 | 119.6 |
C2—C1—C5 | 101.4 (2) | C16—C17—H17 | 119.6 |
C23—C1—H1 | 106.5 | C19—C18—C17 | 119.3 (4) |
C2—C1—H1 | 106.5 | C19—C18—H18 | 120.4 |
C5—C1—H1 | 106.5 | C17—C18—H18 | 120.4 |
C29—C2—C3 | 113.4 (2) | C18—C19—C20 | 121.0 (4) |
C29—C2—C1 | 115.3 (2) | C18—C19—H19 | 119.5 |
C3—C2—C1 | 102.4 (2) | C20—C19—H19 | 119.5 |
C29—C2—H2 | 108.5 | C21—C20—C19 | 119.9 (3) |
C3—C2—H2 | 108.5 | C21—C20—H20 | 120.0 |
C1—C2—H2 | 108.5 | C19—C20—H20 | 120.0 |
C6—C3—C2 | 114.0 (2) | C20—C21—C16 | 118.9 (3) |
C6—C3—C4 | 116.0 (2) | C20—C21—C22 | 124.0 (4) |
C2—C3—C4 | 106.0 (2) | C16—C21—C22 | 116.9 (3) |
C6—C3—H3 | 106.7 | O2—C22—C21 | 109.0 (3) |
C2—C3—H3 | 106.7 | O2—C22—C5 | 113.6 (3) |
C4—C3—H3 | 106.7 | C21—C22—C5 | 115.0 (3) |
O1—C4—C13 | 108.5 (3) | O2—C22—H22 | 106.2 |
O1—C4—C3 | 108.6 (2) | C21—C22—H22 | 106.2 |
C13—C4—C3 | 113.9 (3) | C5—C22—H22 | 106.2 |
O1—C4—C5 | 105.8 (3) | C24—C23—C28 | 117.3 (3) |
C13—C4—C5 | 114.6 (3) | C24—C23—C1 | 120.3 (3) |
C3—C4—C5 | 105.1 (2) | C28—C23—C1 | 122.4 (3) |
C1—C5—C14 | 110.7 (2) | C23—C24—C25 | 122.4 (3) |
C1—C5—C22 | 113.5 (2) | C23—C24—H24 | 118.8 |
C14—C5—C22 | 108.9 (2) | C25—C24—H24 | 118.8 |
C1—C5—C4 | 101.3 (2) | C26—C25—C24 | 118.7 (3) |
C14—C5—C4 | 111.6 (2) | C26—C25—H25 | 120.6 |
C22—C5—C4 | 110.8 (2) | C24—C25—H25 | 120.6 |
C3—C6—C7 | 111.9 (3) | C27—C26—C25 | 120.8 (3) |
C3—C6—H6A | 109.2 | C27—C26—Br1 | 119.2 (3) |
C7—C6—H6A | 109.2 | C25—C26—Br1 | 120.0 (3) |
C3—C6—H6B | 109.2 | C26—C27—C28 | 120.2 (3) |
C7—C6—H6B | 109.2 | C26—C27—H27 | 119.9 |
H6A—C6—H6B | 107.9 | C28—C27—H27 | 119.9 |
C8—C7—C6 | 109.1 (3) | C27—C28—C23 | 120.6 (3) |
C8—C7—H7A | 109.9 | C27—C28—H28 | 119.7 |
C6—C7—H7A | 109.9 | C23—C28—H28 | 119.7 |
C8—C7—H7B | 109.9 | C30—C29—C34 | 117.1 (3) |
C6—C7—H7B | 109.9 | C30—C29—C2 | 121.8 (3) |
H7A—C7—H7B | 108.3 | C34—C29—C2 | 121.1 (3) |
C13—C8—C9 | 119.5 (3) | C29—C30—C31 | 121.6 (3) |
C13—C8—C7 | 120.8 (3) | C29—C30—H30 | 119.2 |
C9—C8—C7 | 119.7 (4) | C31—C30—H30 | 119.2 |
C10—C9—C8 | 121.0 (4) | C32—C31—C30 | 119.5 (3) |
C10—C9—H9 | 119.5 | C32—C31—H31 | 120.3 |
C8—C9—H9 | 119.5 | C30—C31—H31 | 120.3 |
C11—C10—C9 | 119.5 (4) | C33—C32—C31 | 120.0 (3) |
C11—C10—H10 | 120.2 | C33—C32—Br2 | 120.8 (3) |
C9—C10—H10 | 120.2 | C31—C32—Br2 | 119.1 (3) |
C10—C11—C12 | 120.0 (4) | C32—C33—C34 | 120.4 (3) |
C10—C11—H11 | 120.0 | C32—C33—H33 | 119.8 |
C12—C11—H11 | 120.0 | C34—C33—H33 | 119.8 |
C11—C12—C13 | 121.3 (3) | C33—C34—C29 | 121.5 (3) |
C11—C12—H12 | 119.3 | C33—C34—H34 | 119.3 |
C13—C12—H12 | 119.3 | C29—C34—H34 | 119.3 |
C12—C13—C8 | 118.5 (3) | C36—C35—H35A | 109.5 |
C12—C13—C4 | 119.8 (3) | C36—C35—H35B | 109.5 |
C8—C13—C4 | 121.7 (3) | H35A—C35—H35B | 109.5 |
C15—C14—C5 | 114.9 (2) | C36—C35—H35C | 109.5 |
C15—C14—H14A | 108.5 | H35A—C35—H35C | 109.5 |
C5—C14—H14A | 108.5 | H35B—C35—H35C | 109.5 |
C15—C14—H14B | 108.5 | O3—C36—C37 | 124.3 (5) |
C5—C14—H14B | 108.5 | O3—C36—C35 | 121.5 (5) |
H14A—C14—H14B | 107.5 | C37—C36—C35 | 113.8 (4) |
C16—C15—C14 | 109.2 (2) | C36—C37—H37A | 109.5 |
C16—C15—H15A | 109.8 | C36—C37—H37B | 109.5 |
C14—C15—H15A | 109.8 | H37A—C37—H37B | 109.5 |
C16—C15—H15B | 109.8 | C36—C37—H37C | 109.5 |
C14—C15—H15B | 109.8 | H37A—C37—H37C | 109.5 |
H15A—C15—H15B | 108.3 | H37B—C37—H37C | 109.5 |
C17—C16—C21 | 120.2 (3) | ||
C23—C1—C2—C29 | 59.0 (3) | C4—C5—C14—C15 | 103.7 (3) |
C5—C1—C2—C29 | −170.6 (2) | C5—C14—C15—C16 | 58.4 (3) |
C23—C1—C2—C3 | −177.3 (2) | C14—C15—C16—C17 | 132.5 (3) |
C5—C1—C2—C3 | −47.0 (3) | C14—C15—C16—C21 | −44.6 (4) |
C29—C2—C3—C6 | −77.0 (3) | C21—C16—C17—C18 | −1.3 (5) |
C1—C2—C3—C6 | 158.1 (2) | C15—C16—C17—C18 | −178.2 (3) |
C29—C2—C3—C4 | 154.1 (3) | C16—C17—C18—C19 | 1.3 (5) |
C1—C2—C3—C4 | 29.2 (3) | C17—C18—C19—C20 | −0.9 (6) |
C6—C3—C4—O1 | 118.7 (3) | C18—C19—C20—C21 | 0.3 (5) |
C2—C3—C4—O1 | −113.5 (3) | C19—C20—C21—C16 | −0.2 (5) |
C6—C3—C4—C13 | −2.3 (4) | C19—C20—C21—C22 | −174.4 (3) |
C2—C3—C4—C13 | 125.5 (3) | C17—C16—C21—C20 | 0.7 (5) |
C6—C3—C4—C5 | −128.5 (3) | C15—C16—C21—C20 | 177.8 (3) |
C2—C3—C4—C5 | −0.7 (3) | C17—C16—C21—C22 | 175.3 (3) |
C23—C1—C5—C14 | 56.2 (4) | C15—C16—C21—C22 | −7.5 (4) |
C2—C1—C5—C14 | −72.6 (3) | C20—C21—C22—O2 | −7.2 (4) |
C23—C1—C5—C22 | −66.5 (4) | C16—C21—C22—O2 | 178.4 (2) |
C2—C1—C5—C22 | 164.7 (2) | C20—C21—C22—C5 | −136.1 (3) |
C23—C1—C5—C4 | 174.7 (3) | C16—C21—C22—C5 | 49.6 (4) |
C2—C1—C5—C4 | 45.9 (3) | C1—C5—C22—O2 | −35.9 (3) |
O1—C4—C5—C1 | 87.1 (3) | C14—C5—C22—O2 | −159.6 (2) |
C13—C4—C5—C1 | −153.5 (3) | C4—C5—C22—O2 | 77.3 (3) |
C3—C4—C5—C1 | −27.7 (3) | C1—C5—C22—C21 | 90.6 (3) |
O1—C4—C5—C14 | −155.1 (2) | C14—C5—C22—C21 | −33.1 (4) |
C13—C4—C5—C14 | −35.7 (4) | C4—C5—C22—C21 | −156.2 (3) |
C3—C4—C5—C14 | 90.2 (3) | C2—C1—C23—C24 | −151.8 (3) |
O1—C4—C5—C22 | −33.6 (3) | C5—C1—C23—C24 | 86.7 (4) |
C13—C4—C5—C22 | 85.8 (3) | C2—C1—C23—C28 | 26.6 (4) |
C3—C4—C5—C22 | −148.4 (3) | C5—C1—C23—C28 | −94.9 (3) |
C2—C3—C6—C7 | −81.9 (3) | C28—C23—C24—C25 | −0.7 (5) |
C4—C3—C6—C7 | 41.7 (4) | C1—C23—C24—C25 | 177.8 (3) |
C3—C6—C7—C8 | −58.3 (3) | C23—C24—C25—C26 | 0.1 (5) |
C6—C7—C8—C13 | 36.9 (4) | C24—C25—C26—C27 | 0.7 (5) |
C6—C7—C8—C9 | −140.8 (3) | C24—C25—C26—Br1 | −178.1 (2) |
C13—C8—C9—C10 | 0.5 (5) | C25—C26—C27—C28 | −0.7 (5) |
C7—C8—C9—C10 | 178.2 (3) | Br1—C26—C27—C28 | 178.0 (2) |
C8—C9—C10—C11 | −1.1 (6) | C26—C27—C28—C23 | 0.0 (5) |
C9—C10—C11—C12 | 0.3 (6) | C24—C23—C28—C27 | 0.7 (4) |
C10—C11—C12—C13 | 1.0 (5) | C1—C23—C28—C27 | −177.8 (3) |
C11—C12—C13—C8 | −1.6 (5) | C3—C2—C29—C30 | −71.6 (4) |
C11—C12—C13—C4 | 178.2 (3) | C1—C2—C29—C30 | 46.0 (4) |
C9—C8—C13—C12 | 0.8 (5) | C3—C2—C29—C34 | 106.9 (3) |
C7—C8—C13—C12 | −176.9 (3) | C1—C2—C29—C34 | −135.5 (3) |
C9—C8—C13—C4 | −178.9 (3) | C34—C29—C30—C31 | −1.7 (4) |
C7—C8—C13—C4 | 3.4 (5) | C2—C29—C30—C31 | 176.9 (3) |
O1—C4—C13—C12 | 37.7 (4) | C29—C30—C31—C32 | 0.7 (5) |
C3—C4—C13—C12 | 158.7 (3) | C30—C31—C32—C33 | 1.0 (5) |
C5—C4—C13—C12 | −80.2 (4) | C30—C31—C32—Br2 | −177.4 (2) |
O1—C4—C13—C8 | −142.6 (3) | C31—C32—C33—C34 | −1.6 (5) |
C3—C4—C13—C8 | −21.6 (4) | Br2—C32—C33—C34 | 176.7 (2) |
C5—C4—C13—C8 | 99.5 (3) | C32—C33—C34—C29 | 0.6 (5) |
C1—C5—C14—C15 | −144.2 (2) | C30—C29—C34—C33 | 1.0 (5) |
C22—C5—C14—C15 | −18.9 (3) | C2—C29—C34—C33 | −177.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O1 | 0.82 (1) | 1.96 (2) | 2.681 (3) | 147 (3) |
O1—H1O···O3 | 0.81 (1) | 2.04 (1) | 2.842 (3) | 174 (3) |