Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006499/na6147sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006499/na6147Isup2.hkl |
CCDC reference: 185791
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.009 Å
- R factor = 0.060
- wR factor = 0.150
- Data-to-parameter ratio = 12.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 10534 Count of symmetry unique reflns 5818 Completeness (_total/calc) 181.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4716 Fraction of Friedel pairs measured 0.811 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
The title compound was obtained as a white crystalline solid in 90% yield and 97% enantiomeric excess by treatment of (1R,2R,5R,6S)-5,6-bis-(4-methoxybenzyloxymethyl)-2-(methylphenylamino)- cyclohex-3-enol with 4-bromobenzoic acid chloride, pyridine and catalytic 4-(N,N-dimethylamino)pyridine in dichloromethane. Enantiomerically pure crystals were grown from pentane.
All H atoms were included in calculated positions, with C—H distances ranging from 0.95 to 1.00 Å, and then included in the refinement in riding-motion approximation, with Uiso = 1.2Ueq (1.5Ueq for methyl groups) of the carrier atom. 4722 Friedel pairs were used to determine the absolute stereochemistry.
Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C38H40BrNO6 | Z = 2 |
Mr = 686.62 | F(000) = 716 |
Triclinic, P1 | Dx = 1.384 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 7.8180 (2) Å | Cell parameters from 5733 reflections |
b = 11.2850 (3) Å | θ = 2.5–25.0° |
c = 18.6830 (5) Å | µ = 1.30 mm−1 |
α = 90.906 (1)° | T = 150 K |
β = 91.9660 (11)° | Plate, colourless |
γ = 90.0940 (14)° | 0.26 × 0.12 × 0.06 mm |
V = 1647.15 (8) Å3 |
Nonius KappaCCD diffractometer | 10534 independent reflections |
Radiation source: fine-focus sealed tube | 8339 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
ϕ scans, and ω scans with κ offsets | h = −9→9 |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | k = −13→13 |
Tmin = 0.729, Tmax = 0.926 | l = −22→22 |
19157 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.060 | w = 1/[σ2(Fo2) + (0.0675P)2 + 0.8421P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 1.85 e Å−3 |
10534 reflections | Δρmin = −0.41 e Å−3 |
836 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0064 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.010 (9) |
C38H40BrNO6 | γ = 90.0940 (14)° |
Mr = 686.62 | V = 1647.15 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8180 (2) Å | Mo Kα radiation |
b = 11.2850 (3) Å | µ = 1.30 mm−1 |
c = 18.6830 (5) Å | T = 150 K |
α = 90.906 (1)° | 0.26 × 0.12 × 0.06 mm |
β = 91.9660 (11)° |
Nonius KappaCCD diffractometer | 10534 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 8339 reflections with I > 2σ(I) |
Tmin = 0.729, Tmax = 0.926 | Rint = 0.081 |
19157 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.150 | Δρmax = 1.85 e Å−3 |
S = 1.03 | Δρmin = −0.41 e Å−3 |
10534 reflections | Absolute structure: Flack (1983) |
836 parameters | Absolute structure parameter: 0.010 (9) |
3 restraints |
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 | ||
Br1A | 0.42758 (8) | 0.12021 (5) | 0.99509 (4) | 0.0492 (2) | |
C1A | 0.0218 (7) | 0.5099 (5) | 0.6636 (3) | 0.0248 (12) | |
H1AA | −0.0409 | 0.4468 | 0.6351 | 0.030* | |
C2A | 0.1431 (7) | 0.5734 (5) | 0.6145 (3) | 0.0266 (12) | |
H2AA | 0.2125 | 0.5099 | 0.5915 | 0.032* | |
C3A | 0.0339 (7) | 0.6298 (5) | 0.5528 (3) | 0.0278 (13) | |
H3AA | −0.0030 | 0.5631 | 0.5199 | 0.033* | |
C4A | −0.1281 (7) | 0.6866 (6) | 0.5788 (3) | 0.0288 (15) | |
H4AA | −0.1873 | 0.7391 | 0.5474 | 0.035* | |
C5A | −0.1932 (7) | 0.6683 (5) | 0.6422 (3) | 0.0265 (12) | |
H5AA | −0.2981 | 0.7059 | 0.6529 | 0.032* | |
C6A | −0.1091 (7) | 0.5909 (5) | 0.6983 (3) | 0.0233 (13) | |
H6AA | −0.0459 | 0.6439 | 0.7335 | 0.028* | |
N7A | −0.2374 (6) | 0.5255 (4) | 0.7371 (2) | 0.0251 (10) | |
C8A | −0.3391 (7) | 0.4408 (6) | 0.6934 (3) | 0.0334 (14) | |
H8AA | −0.4541 | 0.4349 | 0.7123 | 0.050* | |
H8AB | −0.2840 | 0.3629 | 0.6947 | 0.050* | |
H8AC | −0.3473 | 0.4681 | 0.6438 | 0.050* | |
C9A | −0.2076 (7) | 0.4994 (5) | 0.8100 (3) | 0.0283 (13) | |
C10A | −0.2763 (8) | 0.3981 (5) | 0.8399 (3) | 0.0319 (14) | |
H10A | −0.3381 | 0.3431 | 0.8099 | 0.038* | |
C11A | −0.2562 (9) | 0.3762 (6) | 0.9127 (4) | 0.0434 (17) | |
H11A | −0.3061 | 0.3074 | 0.9320 | 0.052* | |
C12A | −0.1632 (8) | 0.4545 (6) | 0.9572 (3) | 0.0380 (15) | |
H12A | −0.1474 | 0.4389 | 1.0068 | 0.046* | |
C13A | −0.0949 (8) | 0.5541 (6) | 0.9289 (4) | 0.0338 (15) | |
H13A | −0.0310 | 0.6073 | 0.9593 | 0.041* | |
C14A | −0.1165 (7) | 0.5794 (5) | 0.8565 (3) | 0.0271 (14) | |
H14A | −0.0701 | 0.6502 | 0.8383 | 0.033* | |
C15A | 0.2706 (7) | 0.6548 (5) | 0.6536 (3) | 0.0290 (13) | |
H15A | 0.3272 | 0.6110 | 0.6933 | 0.035* | |
H15B | 0.3598 | 0.6780 | 0.6202 | 0.035* | |
O16A | 0.1930 (5) | 0.7595 (3) | 0.6820 (2) | 0.0317 (9) | |
C17A | 0.3116 (8) | 0.8250 (5) | 0.7280 (3) | 0.0341 (14) | |
H17A | 0.2781 | 0.9096 | 0.7284 | 0.041* | |
H17B | 0.4272 | 0.8194 | 0.7082 | 0.041* | |
C18A | 0.3183 (7) | 0.7812 (5) | 0.8033 (3) | 0.0288 (13) | |
C19A | 0.4231 (8) | 0.6881 (6) | 0.8256 (4) | 0.0310 (15) | |
H19A | 0.4969 | 0.6529 | 0.7920 | 0.037* | |
C20A | 0.4245 (8) | 0.6449 (6) | 0.8941 (4) | 0.0345 (16) | |
H20A | 0.4967 | 0.5807 | 0.9073 | 0.041* | |
C21A | 0.3185 (9) | 0.6970 (7) | 0.9435 (3) | 0.0435 (17) | |
C22A | 0.2162 (9) | 0.7923 (7) | 0.9234 (4) | 0.0464 (18) | |
H22A | 0.1462 | 0.8298 | 0.9576 | 0.056* | |
C23A | 0.2157 (8) | 0.8322 (6) | 0.8549 (4) | 0.0428 (17) | |
H23A | 0.1434 | 0.8966 | 0.8419 | 0.051* | |
O24A | 0.3046 (7) | 0.6618 (6) | 1.0125 (3) | 0.0673 (16) | |
C25A | 0.4154 (14) | 0.5709 (10) | 1.0377 (5) | 0.074 (3) | |
H25A | 0.4047 | 0.5629 | 1.0895 | 0.111* | |
H25B | 0.5339 | 0.5912 | 1.0273 | 0.111* | |
H25C | 0.3842 | 0.4958 | 1.0135 | 0.111* | |
C26A | 0.1343 (7) | 0.7138 (5) | 0.5086 (3) | 0.0307 (13) | |
H26A | 0.0631 | 0.7408 | 0.4672 | 0.037* | |
H26B | 0.1697 | 0.7841 | 0.5379 | 0.037* | |
O27A | 0.2811 (5) | 0.6528 (4) | 0.4843 (2) | 0.0382 (11) | |
C28A | 0.3958 (8) | 0.7281 (7) | 0.4467 (4) | 0.0405 (18) | |
H28A | 0.5107 | 0.6912 | 0.4475 | 0.049* | |
H28B | 0.4059 | 0.8051 | 0.4726 | 0.049* | |
C29A | 0.3412 (7) | 0.7501 (5) | 0.3709 (3) | 0.0311 (14) | |
C30A | 0.3790 (8) | 0.6677 (6) | 0.3176 (4) | 0.0386 (18) | |
H30A | 0.4317 | 0.5947 | 0.3302 | 0.046* | |
C31A | 0.3406 (9) | 0.6912 (6) | 0.2467 (4) | 0.0417 (17) | |
H31A | 0.3683 | 0.6341 | 0.2110 | 0.050* | |
C32A | 0.2624 (8) | 0.7966 (6) | 0.2261 (3) | 0.0337 (14) | |
C33A | 0.2156 (7) | 0.8764 (5) | 0.2782 (3) | 0.0310 (13) | |
H33A | 0.1549 | 0.9464 | 0.2657 | 0.037* | |
C34A | 0.2587 (7) | 0.8533 (5) | 0.3504 (3) | 0.0317 (14) | |
H34A | 0.2305 | 0.9102 | 0.3861 | 0.038* | |
O35A | 0.2404 (6) | 0.8124 (4) | 0.1544 (2) | 0.0473 (12) | |
C36A | 0.1474 (12) | 0.9126 (7) | 0.1323 (4) | 0.058 (2) | |
H36A | 0.1344 | 0.9118 | 0.0800 | 0.086* | |
H36B | 0.2088 | 0.9845 | 0.1484 | 0.086* | |
H36C | 0.0342 | 0.9113 | 0.1532 | 0.086* | |
O37A | 0.1136 (5) | 0.4548 (3) | 0.7229 (2) | 0.0262 (9) | |
C38A | 0.1886 (7) | 0.3490 (5) | 0.7131 (3) | 0.0260 (13) | |
O39A | 0.2001 (6) | 0.3012 (4) | 0.6540 (2) | 0.0394 (11) | |
C40A | 0.2543 (7) | 0.2985 (5) | 0.7814 (3) | 0.0280 (13) | |
C41A | 0.2114 (7) | 0.3490 (5) | 0.8472 (3) | 0.0297 (13) | |
H41A | 0.1463 | 0.4199 | 0.8485 | 0.036* | |
C42A | 0.2636 (7) | 0.2957 (5) | 0.9105 (3) | 0.0321 (14) | |
H42A | 0.2353 | 0.3299 | 0.9554 | 0.039* | |
C43A | 0.3575 (8) | 0.1919 (5) | 0.9077 (3) | 0.0345 (14) | |
C44A | 0.4039 (8) | 0.1412 (6) | 0.8427 (4) | 0.0332 (16) | |
H44A | 0.4713 | 0.0713 | 0.8415 | 0.040* | |
C45A | 0.3505 (7) | 0.1942 (5) | 0.7806 (3) | 0.0317 (14) | |
H45A | 0.3794 | 0.1594 | 0.7360 | 0.038* | |
Br1B | 0.87576 (8) | 0.64358 (5) | 0.15048 (4) | 0.0500 (2) | |
C1B | 0.5075 (7) | 0.2554 (5) | 0.4790 (3) | 0.0247 (12) | |
H1BA | 0.4498 | 0.3185 | 0.5075 | 0.030* | |
C2B | 0.6358 (7) | 0.1910 (5) | 0.5283 (3) | 0.0242 (12) | |
H2BA | 0.7093 | 0.2542 | 0.5516 | 0.029* | |
C3B | 0.5363 (7) | 0.1346 (5) | 0.5892 (3) | 0.0265 (12) | |
H3BA | 0.5058 | 0.2012 | 0.6223 | 0.032* | |
C4B | 0.3690 (7) | 0.0783 (5) | 0.5638 (3) | 0.0271 (14) | |
H4BA | 0.3143 | 0.0265 | 0.5955 | 0.032* | |
C5B | 0.2935 (7) | 0.0962 (5) | 0.5005 (3) | 0.0290 (13) | |
H5BA | 0.1865 | 0.0587 | 0.4899 | 0.035* | |
C6B | 0.3688 (7) | 0.1729 (5) | 0.4442 (3) | 0.0234 (13) | |
H6BA | 0.4268 | 0.1193 | 0.4096 | 0.028* | |
N7B | 0.2367 (6) | 0.2389 (4) | 0.4036 (3) | 0.0272 (10) | |
C8B | 0.1419 (8) | 0.3239 (6) | 0.4470 (4) | 0.0377 (16) | |
H8BA | 0.0266 | 0.3341 | 0.4258 | 0.057* | |
H8BB | 0.2019 | 0.4002 | 0.4486 | 0.057* | |
H8BC | 0.1338 | 0.2941 | 0.4958 | 0.057* | |
C9B | 0.2558 (7) | 0.2631 (5) | 0.3319 (3) | 0.0256 (12) | |
C10B | 0.1820 (8) | 0.3649 (5) | 0.3005 (4) | 0.0349 (14) | |
H10B | 0.1229 | 0.4199 | 0.3296 | 0.042* | |
C11B | 0.1942 (9) | 0.3860 (6) | 0.2282 (4) | 0.0426 (16) | |
H11B | 0.1432 | 0.4555 | 0.2090 | 0.051* | |
C12B | 0.2781 (8) | 0.3095 (6) | 0.1830 (3) | 0.0355 (14) | |
H12B | 0.2845 | 0.3246 | 0.1332 | 0.043* | |
C13B | 0.3529 (8) | 0.2094 (6) | 0.2131 (4) | 0.0337 (15) | |
H13B | 0.4118 | 0.1554 | 0.1833 | 0.040* | |
C14B | 0.3436 (8) | 0.1868 (6) | 0.2850 (3) | 0.0317 (14) | |
H14B | 0.3977 | 0.1180 | 0.3036 | 0.038* | |
C15B | 0.7563 (7) | 0.1098 (5) | 0.4890 (3) | 0.0265 (12) | |
H15C | 0.8066 | 0.1538 | 0.4493 | 0.032* | |
H15D | 0.8510 | 0.0863 | 0.5223 | 0.032* | |
O16B | 0.6729 (5) | 0.0051 (3) | 0.4604 (2) | 0.0267 (9) | |
C17B | 0.7833 (7) | −0.0616 (5) | 0.4150 (3) | 0.0302 (13) | |
H17C | 0.7479 | −0.1459 | 0.4146 | 0.036* | |
H17D | 0.9020 | −0.0568 | 0.4350 | 0.036* | |
C18B | 0.7800 (7) | −0.0180 (5) | 0.3391 (3) | 0.0238 (12) | |
C19B | 0.8826 (8) | 0.0765 (6) | 0.3180 (3) | 0.0276 (14) | |
H19B | 0.9606 | 0.1128 | 0.3518 | 0.033* | |
C20B | 0.8715 (9) | 0.1174 (6) | 0.2488 (4) | 0.0333 (15) | |
H20B | 0.9416 | 0.1814 | 0.2352 | 0.040* | |
C21B | 0.7573 (8) | 0.0647 (6) | 0.1989 (3) | 0.0330 (14) | |
C22B | 0.6588 (8) | −0.0300 (6) | 0.2185 (3) | 0.0361 (15) | |
H22B | 0.5833 | −0.0674 | 0.1841 | 0.043* | |
C23B | 0.6694 (8) | −0.0707 (6) | 0.2878 (3) | 0.0340 (14) | |
H23B | 0.6002 | −0.1357 | 0.3007 | 0.041* | |
O24B | 0.7365 (6) | 0.0991 (4) | 0.1282 (2) | 0.0421 (11) | |
C25B | 0.8477 (11) | 0.1877 (7) | 0.1034 (4) | 0.049 (2) | |
H25D | 0.8172 | 0.2052 | 0.0534 | 0.073* | |
H25E | 0.9661 | 0.1594 | 0.1069 | 0.073* | |
H25F | 0.8367 | 0.2599 | 0.1328 | 0.073* | |
C26B | 0.6440 (7) | 0.0491 (5) | 0.6336 (3) | 0.0309 (13) | |
H26C | 0.5792 | 0.0216 | 0.6748 | 0.037* | |
H26D | 0.6747 | −0.0208 | 0.6041 | 0.037* | |
O27B | 0.7950 (5) | 0.1108 (4) | 0.6582 (2) | 0.0342 (10) | |
C28B | 0.9146 (8) | 0.0359 (6) | 0.6945 (4) | 0.0348 (16) | |
H28C | 1.0296 | 0.0727 | 0.6936 | 0.042* | |
H28D | 0.9196 | −0.0408 | 0.6683 | 0.042* | |
C29B | 0.8720 (7) | 0.0129 (5) | 0.7718 (3) | 0.0274 (13) | |
C30B | 0.9225 (8) | 0.0961 (6) | 0.8256 (4) | 0.0331 (16) | |
H30B | 0.9755 | 0.1680 | 0.8125 | 0.040* | |
C31B | 0.8967 (8) | 0.0751 (6) | 0.8969 (4) | 0.0333 (15) | |
H31B | 0.9329 | 0.1316 | 0.9325 | 0.040* | |
C32B | 0.8176 (7) | −0.0290 (5) | 0.9164 (3) | 0.0296 (13) | |
C33B | 0.7622 (7) | −0.1109 (5) | 0.8649 (3) | 0.0310 (13) | |
H33B | 0.7053 | −0.1812 | 0.8783 | 0.037* | |
C34B | 0.7912 (8) | −0.0889 (5) | 0.7928 (3) | 0.0331 (14) | |
H34B | 0.7542 | −0.1456 | 0.7574 | 0.040* | |
O35B | 0.8076 (6) | −0.0440 (4) | 0.9888 (2) | 0.0375 (10) | |
C36B | 0.7122 (10) | −0.1436 (6) | 1.0116 (4) | 0.0474 (18) | |
H36D | 0.7162 | −0.1460 | 1.0641 | 0.071* | |
H36E | 0.7619 | −0.2166 | 0.9923 | 0.071* | |
H36F | 0.5930 | −0.1368 | 0.9942 | 0.071* | |
O37B | 0.5885 (5) | 0.3099 (3) | 0.4195 (2) | 0.0278 (9) | |
C38B | 0.6652 (7) | 0.4168 (5) | 0.4309 (3) | 0.0291 (13) | |
O39B | 0.6840 (6) | 0.4646 (4) | 0.4888 (2) | 0.0381 (10) | |
C40B | 0.7215 (7) | 0.4668 (5) | 0.3620 (3) | 0.0271 (12) | |
C41B | 0.6731 (7) | 0.4152 (5) | 0.2960 (3) | 0.0310 (14) | |
H41B | 0.6101 | 0.3431 | 0.2940 | 0.037* | |
C42B | 0.7179 (8) | 0.4702 (5) | 0.2332 (3) | 0.0331 (14) | |
H42B | 0.6822 | 0.4374 | 0.1880 | 0.040* | |
C43B | 0.8149 (8) | 0.5729 (5) | 0.2371 (4) | 0.0347 (15) | |
C44B | 0.8648 (8) | 0.6242 (6) | 0.3014 (4) | 0.0330 (16) | |
H44B | 0.9309 | 0.6950 | 0.3028 | 0.040* | |
C45B | 0.8179 (7) | 0.5717 (5) | 0.3649 (4) | 0.0333 (14) | |
H45B | 0.8509 | 0.6069 | 0.4098 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1A | 0.0582 (5) | 0.0503 (5) | 0.0395 (4) | 0.0114 (4) | −0.0021 (3) | 0.0167 (3) |
C1A | 0.026 (3) | 0.024 (3) | 0.024 (3) | 0.002 (2) | 0.002 (2) | 0.004 (2) |
C2A | 0.024 (3) | 0.028 (3) | 0.029 (3) | 0.003 (2) | 0.003 (2) | 0.003 (2) |
C3A | 0.026 (3) | 0.028 (3) | 0.030 (3) | 0.001 (2) | 0.002 (2) | 0.007 (2) |
C4A | 0.020 (3) | 0.039 (4) | 0.028 (3) | 0.004 (3) | −0.003 (2) | 0.008 (3) |
C5A | 0.024 (3) | 0.022 (3) | 0.034 (3) | 0.000 (2) | 0.003 (2) | 0.002 (2) |
C6A | 0.018 (3) | 0.027 (3) | 0.025 (3) | 0.001 (2) | 0.002 (2) | 0.000 (3) |
N7A | 0.023 (2) | 0.028 (3) | 0.024 (3) | −0.007 (2) | 0.0039 (19) | −0.003 (2) |
C8A | 0.027 (3) | 0.035 (3) | 0.039 (4) | −0.004 (3) | 0.003 (3) | 0.000 (3) |
C9A | 0.028 (3) | 0.022 (3) | 0.035 (3) | 0.004 (2) | 0.007 (2) | 0.002 (2) |
C10A | 0.032 (3) | 0.024 (3) | 0.040 (4) | −0.004 (3) | 0.000 (3) | 0.007 (3) |
C11A | 0.046 (4) | 0.037 (4) | 0.048 (4) | 0.002 (3) | 0.006 (3) | 0.018 (3) |
C12A | 0.046 (4) | 0.040 (4) | 0.029 (3) | 0.005 (3) | 0.003 (3) | 0.005 (3) |
C13A | 0.034 (4) | 0.031 (4) | 0.036 (4) | 0.007 (3) | 0.003 (3) | −0.001 (3) |
C14A | 0.021 (3) | 0.030 (3) | 0.030 (3) | 0.004 (3) | 0.005 (2) | −0.001 (3) |
C15A | 0.017 (3) | 0.033 (3) | 0.037 (3) | 0.005 (2) | 0.000 (2) | 0.002 (3) |
O16A | 0.025 (2) | 0.028 (2) | 0.041 (3) | −0.0009 (17) | −0.0073 (18) | −0.0007 (19) |
C17A | 0.028 (3) | 0.026 (3) | 0.047 (4) | −0.007 (3) | −0.012 (3) | −0.001 (3) |
C18A | 0.022 (3) | 0.027 (3) | 0.037 (3) | −0.005 (2) | −0.006 (2) | −0.004 (3) |
C19A | 0.029 (3) | 0.028 (4) | 0.036 (4) | 0.000 (3) | 0.003 (3) | −0.003 (3) |
C20A | 0.030 (4) | 0.033 (4) | 0.040 (4) | −0.004 (3) | −0.005 (3) | −0.002 (3) |
C21A | 0.048 (4) | 0.053 (4) | 0.029 (4) | −0.006 (3) | 0.000 (3) | −0.010 (3) |
C22A | 0.037 (4) | 0.064 (5) | 0.039 (4) | 0.010 (3) | 0.004 (3) | −0.018 (4) |
C23A | 0.032 (4) | 0.039 (4) | 0.056 (5) | 0.007 (3) | −0.002 (3) | −0.017 (3) |
O24A | 0.065 (4) | 0.104 (5) | 0.032 (3) | −0.002 (3) | 0.001 (2) | −0.002 (3) |
C25A | 0.100 (8) | 0.086 (8) | 0.036 (5) | −0.020 (6) | −0.006 (5) | 0.008 (5) |
C26A | 0.024 (3) | 0.033 (3) | 0.036 (3) | 0.007 (2) | 0.006 (2) | 0.008 (3) |
O27A | 0.029 (2) | 0.041 (3) | 0.046 (3) | 0.0063 (19) | 0.0103 (19) | 0.018 (2) |
C28A | 0.029 (4) | 0.041 (4) | 0.053 (5) | 0.000 (3) | 0.012 (3) | 0.017 (4) |
C29A | 0.020 (3) | 0.032 (3) | 0.042 (4) | −0.007 (3) | 0.008 (3) | 0.010 (3) |
C30A | 0.029 (3) | 0.028 (4) | 0.060 (5) | 0.000 (3) | 0.006 (3) | −0.001 (4) |
C31A | 0.038 (4) | 0.039 (4) | 0.048 (4) | 0.000 (3) | 0.000 (3) | −0.008 (3) |
C32A | 0.030 (3) | 0.038 (4) | 0.033 (3) | −0.008 (3) | 0.002 (3) | 0.002 (3) |
C33A | 0.031 (3) | 0.029 (3) | 0.033 (3) | −0.004 (2) | 0.007 (3) | 0.000 (3) |
C34A | 0.032 (3) | 0.028 (3) | 0.035 (3) | −0.001 (3) | 0.010 (3) | 0.001 (3) |
O35A | 0.052 (3) | 0.052 (3) | 0.037 (3) | −0.003 (2) | 0.004 (2) | −0.006 (2) |
C36A | 0.089 (6) | 0.052 (5) | 0.031 (4) | −0.015 (4) | 0.001 (4) | 0.007 (3) |
O37A | 0.030 (2) | 0.022 (2) | 0.027 (2) | 0.0060 (17) | −0.0024 (17) | 0.0032 (17) |
C38A | 0.017 (3) | 0.022 (3) | 0.039 (4) | 0.002 (2) | 0.007 (2) | 0.003 (3) |
O39A | 0.050 (3) | 0.035 (2) | 0.033 (3) | 0.015 (2) | 0.002 (2) | −0.001 (2) |
C40A | 0.024 (3) | 0.024 (3) | 0.037 (3) | 0.000 (2) | 0.004 (2) | 0.006 (3) |
C41A | 0.028 (3) | 0.025 (3) | 0.036 (3) | 0.004 (2) | −0.001 (3) | 0.002 (3) |
C42A | 0.032 (3) | 0.035 (3) | 0.029 (3) | 0.001 (3) | −0.004 (3) | −0.003 (3) |
C43A | 0.032 (3) | 0.032 (3) | 0.040 (4) | −0.005 (3) | −0.001 (3) | 0.007 (3) |
C44A | 0.020 (3) | 0.036 (4) | 0.044 (4) | 0.002 (3) | 0.004 (3) | 0.000 (3) |
C45A | 0.027 (3) | 0.030 (3) | 0.039 (4) | −0.001 (3) | 0.008 (3) | 0.006 (3) |
Br1B | 0.0638 (5) | 0.0461 (4) | 0.0403 (4) | −0.0138 (3) | −0.0036 (3) | 0.0176 (3) |
C1B | 0.023 (3) | 0.024 (3) | 0.027 (3) | −0.006 (2) | 0.004 (2) | 0.001 (2) |
C2B | 0.022 (3) | 0.024 (3) | 0.027 (3) | −0.002 (2) | 0.001 (2) | 0.004 (2) |
C3B | 0.024 (3) | 0.035 (3) | 0.021 (3) | 0.000 (2) | 0.004 (2) | 0.001 (2) |
C4B | 0.022 (3) | 0.024 (3) | 0.035 (4) | −0.006 (2) | 0.007 (3) | 0.003 (3) |
C5B | 0.025 (3) | 0.029 (3) | 0.034 (3) | 0.001 (2) | 0.009 (2) | 0.000 (3) |
C6B | 0.024 (3) | 0.018 (3) | 0.028 (3) | 0.001 (2) | 0.000 (2) | 0.003 (3) |
N7B | 0.022 (2) | 0.028 (3) | 0.032 (3) | 0.004 (2) | 0.001 (2) | −0.002 (2) |
C8B | 0.035 (4) | 0.039 (4) | 0.040 (4) | 0.012 (3) | 0.002 (3) | −0.009 (3) |
C9B | 0.024 (3) | 0.020 (3) | 0.031 (3) | −0.004 (2) | −0.005 (2) | −0.006 (2) |
C10B | 0.034 (3) | 0.028 (3) | 0.043 (4) | 0.003 (3) | −0.001 (3) | 0.004 (3) |
C11B | 0.051 (4) | 0.033 (4) | 0.044 (4) | 0.003 (3) | 0.000 (3) | 0.014 (3) |
C12B | 0.037 (3) | 0.042 (4) | 0.028 (3) | −0.006 (3) | −0.007 (3) | 0.006 (3) |
C13B | 0.035 (4) | 0.033 (4) | 0.032 (4) | 0.000 (3) | −0.002 (3) | −0.005 (3) |
C14B | 0.036 (4) | 0.029 (3) | 0.030 (4) | 0.000 (3) | −0.006 (3) | 0.002 (3) |
C15B | 0.028 (3) | 0.025 (3) | 0.027 (3) | −0.002 (2) | 0.003 (2) | 0.000 (2) |
O16B | 0.026 (2) | 0.025 (2) | 0.029 (2) | 0.0008 (16) | 0.0060 (16) | 0.0016 (17) |
C17B | 0.030 (3) | 0.029 (3) | 0.032 (3) | 0.002 (3) | 0.005 (3) | 0.005 (3) |
C18B | 0.020 (3) | 0.029 (3) | 0.023 (3) | 0.003 (2) | 0.006 (2) | 0.002 (2) |
C19B | 0.024 (3) | 0.032 (4) | 0.026 (4) | −0.005 (3) | 0.002 (3) | 0.002 (3) |
C20B | 0.040 (4) | 0.030 (4) | 0.030 (4) | −0.004 (3) | 0.005 (3) | 0.002 (3) |
C21B | 0.042 (4) | 0.038 (4) | 0.019 (3) | 0.000 (3) | 0.005 (3) | 0.001 (3) |
C22B | 0.030 (3) | 0.044 (4) | 0.033 (4) | −0.009 (3) | −0.003 (3) | −0.004 (3) |
C23B | 0.032 (3) | 0.032 (3) | 0.038 (4) | −0.003 (3) | 0.010 (3) | −0.002 (3) |
O24B | 0.041 (3) | 0.056 (3) | 0.029 (2) | −0.011 (2) | 0.0006 (19) | 0.003 (2) |
C25B | 0.079 (6) | 0.040 (4) | 0.028 (4) | −0.004 (4) | 0.006 (4) | 0.012 (3) |
C26B | 0.027 (3) | 0.035 (3) | 0.031 (3) | −0.007 (3) | 0.007 (2) | 0.005 (3) |
O27B | 0.033 (2) | 0.034 (2) | 0.035 (2) | 0.0015 (18) | −0.0035 (18) | 0.0080 (19) |
C28B | 0.031 (4) | 0.046 (4) | 0.027 (4) | −0.003 (3) | −0.004 (3) | 0.006 (3) |
C29B | 0.018 (3) | 0.029 (3) | 0.035 (3) | 0.002 (2) | −0.001 (2) | 0.001 (3) |
C30B | 0.037 (4) | 0.024 (3) | 0.039 (4) | −0.005 (3) | 0.004 (3) | 0.003 (3) |
C31B | 0.030 (3) | 0.029 (3) | 0.040 (4) | −0.008 (3) | 0.002 (3) | −0.010 (3) |
C32B | 0.028 (3) | 0.034 (3) | 0.027 (3) | 0.003 (3) | −0.001 (2) | 0.000 (3) |
C33B | 0.031 (3) | 0.027 (3) | 0.035 (3) | 0.000 (3) | −0.001 (3) | 0.001 (3) |
C34B | 0.038 (3) | 0.026 (3) | 0.034 (3) | −0.002 (3) | −0.011 (3) | −0.003 (3) |
O35B | 0.043 (3) | 0.038 (2) | 0.032 (2) | −0.001 (2) | 0.0026 (19) | 0.0007 (19) |
C36B | 0.064 (5) | 0.040 (4) | 0.040 (4) | 0.004 (3) | 0.012 (3) | 0.013 (3) |
O37B | 0.031 (2) | 0.026 (2) | 0.026 (2) | −0.0084 (17) | 0.0000 (17) | 0.0025 (17) |
C38B | 0.026 (3) | 0.023 (3) | 0.038 (4) | 0.002 (2) | 0.000 (3) | 0.005 (3) |
O39B | 0.048 (3) | 0.034 (2) | 0.032 (3) | −0.012 (2) | 0.005 (2) | −0.005 (2) |
C40B | 0.028 (3) | 0.021 (3) | 0.032 (3) | 0.004 (2) | −0.002 (2) | 0.001 (2) |
C41B | 0.032 (3) | 0.024 (3) | 0.037 (4) | −0.010 (3) | 0.003 (3) | 0.002 (3) |
C42B | 0.038 (4) | 0.030 (3) | 0.031 (3) | 0.001 (3) | 0.000 (3) | −0.001 (3) |
C43B | 0.029 (3) | 0.031 (3) | 0.045 (4) | −0.003 (3) | 0.002 (3) | 0.011 (3) |
C44B | 0.041 (4) | 0.021 (3) | 0.037 (4) | −0.006 (3) | −0.007 (3) | 0.005 (3) |
C45B | 0.026 (3) | 0.030 (3) | 0.044 (4) | −0.007 (3) | −0.004 (3) | 0.004 (3) |
Br1A—C43A | 1.898 (6) | Br1B—C43B | 1.890 (6) |
C1A—O37A | 1.448 (6) | C1B—O37B | 1.444 (6) |
C1A—C6A | 1.527 (8) | C1B—C2B | 1.530 (7) |
C1A—C2A | 1.528 (7) | C1B—C6B | 1.547 (8) |
C1A—H1AA | 1.0000 | C1B—H1BA | 1.0000 |
C2A—C15A | 1.515 (8) | C2B—C15B | 1.515 (8) |
C2A—C3A | 1.555 (8) | C2B—C3B | 1.544 (7) |
C2A—H2AA | 1.0000 | C2B—H2BA | 1.0000 |
C3A—C26A | 1.504 (8) | C3B—C4B | 1.512 (8) |
C3A—C4A | 1.512 (8) | C3B—C26B | 1.520 (8) |
C3A—H3AA | 1.0000 | C3B—H3BA | 1.0000 |
C4A—C5A | 1.324 (9) | C4B—C5B | 1.323 (9) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.509 (8) | C5B—C6B | 1.507 (8) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—N7A | 1.464 (7) | C6B—N7B | 1.471 (7) |
C6A—H6AA | 1.0000 | C6B—H6BA | 1.0000 |
N7A—C9A | 1.409 (7) | N7B—C9B | 1.385 (7) |
N7A—C8A | 1.463 (8) | N7B—C8B | 1.465 (8) |
C8A—H8AA | 0.9800 | C8B—H8BA | 0.9800 |
C8A—H8AB | 0.9800 | C8B—H8BB | 0.9800 |
C8A—H8AC | 0.9800 | C8B—H8BC | 0.9800 |
C9A—C10A | 1.395 (8) | C9B—C10B | 1.414 (8) |
C9A—C14A | 1.417 (9) | C9B—C14B | 1.414 (8) |
C10A—C11A | 1.390 (9) | C10B—C11B | 1.382 (9) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.392 (10) | C11B—C12B | 1.381 (9) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.366 (9) | C12B—C13B | 1.390 (9) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.391 (9) | C13B—C14B | 1.375 (9) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C15A—O16A | 1.432 (7) | C15B—O16B | 1.436 (7) |
C15A—H15A | 0.9900 | C15B—H15C | 0.9900 |
C15A—H15B | 0.9900 | C15B—H15D | 0.9900 |
O16A—C17A | 1.437 (7) | O16B—C17B | 1.437 (7) |
C17A—C18A | 1.499 (9) | C17B—C18B | 1.507 (8) |
C17A—H17A | 0.9900 | C17B—H17C | 0.9900 |
C17A—H17B | 0.9900 | C17B—H17D | 0.9900 |
C18A—C23A | 1.392 (9) | C18B—C23B | 1.394 (8) |
C18A—C19A | 1.394 (9) | C18B—C19B | 1.403 (8) |
C19A—C20A | 1.376 (10) | C19B—C20B | 1.380 (9) |
C19A—H19A | 0.9500 | C19B—H19B | 0.9500 |
C20A—C21A | 1.386 (10) | C20B—C21B | 1.394 (9) |
C20A—H20A | 0.9500 | C20B—H20B | 0.9500 |
C21A—O24A | 1.363 (8) | C21B—C22B | 1.378 (9) |
C21A—C22A | 1.390 (10) | C21B—O24B | 1.387 (7) |
C22A—C23A | 1.364 (10) | C22B—C23B | 1.381 (9) |
C22A—H22A | 0.9500 | C22B—H22B | 0.9500 |
C23A—H23A | 0.9500 | C23B—H23B | 0.9500 |
O24A—C25A | 1.419 (12) | O24B—C25B | 1.418 (9) |
C25A—H25A | 0.9800 | C25B—H25D | 0.9800 |
C25A—H25B | 0.9800 | C25B—H25E | 0.9800 |
C25A—H25C | 0.9800 | C25B—H25F | 0.9800 |
C26A—O27A | 1.423 (7) | C26B—O27B | 1.428 (7) |
C26A—H26A | 0.9900 | C26B—H26C | 0.9900 |
C26A—H26B | 0.9900 | C26B—H26D | 0.9900 |
O27A—C28A | 1.442 (8) | O27B—C28B | 1.424 (7) |
C28A—C29A | 1.491 (10) | C28B—C29B | 1.519 (9) |
C28A—H28A | 0.9900 | C28B—H28C | 0.9900 |
C28A—H28B | 0.9900 | C28B—H28D | 0.9900 |
C29A—C34A | 1.385 (8) | C29B—C34B | 1.379 (8) |
C29A—C30A | 1.391 (10) | C29B—C30B | 1.411 (9) |
C30A—C31A | 1.378 (11) | C30B—C31B | 1.378 (10) |
C30A—H30A | 0.9500 | C30B—H30B | 0.9500 |
C31A—C32A | 1.392 (9) | C31B—C32B | 1.385 (9) |
C31A—H31A | 0.9500 | C31B—H31B | 0.9500 |
C32A—O35A | 1.360 (8) | C32B—O35B | 1.372 (7) |
C32A—C33A | 1.375 (9) | C32B—C33B | 1.382 (8) |
C33A—C34A | 1.407 (9) | C33B—C34B | 1.400 (9) |
C33A—H33A | 0.9500 | C33B—H33B | 0.9500 |
C34A—H34A | 0.9500 | C34B—H34B | 0.9500 |
O35A—C36A | 1.404 (9) | O35B—C36B | 1.428 (8) |
C36A—H36A | 0.9800 | C36B—H36D | 0.9800 |
C36A—H36B | 0.9800 | C36B—H36E | 0.9800 |
C36A—H36C | 0.9800 | C36B—H36F | 0.9800 |
O37A—C38A | 1.345 (7) | O37B—C38B | 1.357 (7) |
C38A—O39A | 1.226 (7) | C38B—O39B | 1.204 (7) |
C38A—C40A | 1.482 (8) | C38B—C40B | 1.493 (8) |
C40A—C45A | 1.399 (8) | C40B—C41B | 1.396 (8) |
C40A—C41A | 1.399 (8) | C40B—C45B | 1.402 (8) |
C41A—C42A | 1.385 (8) | C41B—C42B | 1.391 (8) |
C41A—H41A | 0.9500 | C41B—H41B | 0.9500 |
C42A—C43A | 1.384 (9) | C42B—C43B | 1.383 (9) |
C42A—H42A | 0.9500 | C42B—H42B | 0.9500 |
C43A—C44A | 1.394 (9) | C43B—C44B | 1.371 (9) |
C44A—C45A | 1.365 (9) | C44B—C45B | 1.394 (9) |
C44A—H44A | 0.9500 | C44B—H44B | 0.9500 |
C45A—H45A | 0.9500 | C45B—H45B | 0.9500 |
O37A—C1A—C6A | 105.0 (4) | O37B—C1B—C2B | 112.4 (4) |
O37A—C1A—C2A | 111.7 (4) | O37B—C1B—C6B | 104.8 (4) |
C6A—C1A—C2A | 114.2 (5) | C2B—C1B—C6B | 113.6 (4) |
O37A—C1A—H1AA | 108.6 | O37B—C1B—H1BA | 108.6 |
C6A—C1A—H1AA | 108.6 | C2B—C1B—H1BA | 108.6 |
C2A—C1A—H1AA | 108.6 | C6B—C1B—H1BA | 108.6 |
C15A—C2A—C1A | 114.0 (5) | C15B—C2B—C1B | 113.8 (5) |
C15A—C2A—C3A | 116.2 (5) | C15B—C2B—C3B | 116.2 (5) |
C1A—C2A—C3A | 108.1 (4) | C1B—C2B—C3B | 108.2 (4) |
C15A—C2A—H2AA | 105.9 | C15B—C2B—H2BA | 105.9 |
C1A—C2A—H2AA | 105.9 | C1B—C2B—H2BA | 105.9 |
C3A—C2A—H2AA | 105.9 | C3B—C2B—H2BA | 105.9 |
C26A—C3A—C4A | 111.5 (5) | C4B—C3B—C26B | 111.2 (5) |
C26A—C3A—C2A | 113.1 (5) | C4B—C3B—C2B | 113.3 (5) |
C4A—C3A—C2A | 112.6 (5) | C26B—C3B—C2B | 113.0 (4) |
C26A—C3A—H3AA | 106.4 | C4B—C3B—H3BA | 106.2 |
C4A—C3A—H3AA | 106.4 | C26B—C3B—H3BA | 106.2 |
C2A—C3A—H3AA | 106.4 | C2B—C3B—H3BA | 106.2 |
C5A—C4A—C3A | 124.6 (6) | C5B—C4B—C3B | 124.5 (5) |
C5A—C4A—H4AA | 117.7 | C5B—C4B—H4BA | 117.8 |
C3A—C4A—H4AA | 117.7 | C3B—C4B—H4BA | 117.8 |
C4A—C5A—C6A | 123.3 (6) | C4B—C5B—C6B | 123.3 (5) |
C4A—C5A—H5AA | 118.3 | C4B—C5B—H5BA | 118.4 |
C6A—C5A—H5AA | 118.3 | C6B—C5B—H5BA | 118.4 |
N7A—C6A—C5A | 110.9 (5) | N7B—C6B—C5B | 112.2 (5) |
N7A—C6A—C1A | 112.8 (5) | N7B—C6B—C1B | 112.4 (5) |
C5A—C6A—C1A | 109.8 (5) | C5B—C6B—C1B | 109.9 (5) |
N7A—C6A—H6AA | 107.7 | N7B—C6B—H6BA | 107.4 |
C5A—C6A—H6AA | 107.7 | C5B—C6B—H6BA | 107.4 |
C1A—C6A—H6AA | 107.7 | C1B—C6B—H6BA | 107.4 |
C9A—N7A—C8A | 117.7 (5) | C9B—N7B—C8B | 118.2 (5) |
C9A—N7A—C6A | 120.0 (5) | C9B—N7B—C6B | 120.8 (5) |
C8A—N7A—C6A | 114.8 (5) | C8B—N7B—C6B | 114.0 (5) |
N7A—C8A—H8AA | 109.5 | N7B—C8B—H8BA | 109.5 |
N7A—C8A—H8AB | 109.5 | N7B—C8B—H8BB | 109.5 |
H8AA—C8A—H8AB | 109.5 | H8BA—C8B—H8BB | 109.5 |
N7A—C8A—H8AC | 109.5 | N7B—C8B—H8BC | 109.5 |
H8AA—C8A—H8AC | 109.5 | H8BA—C8B—H8BC | 109.5 |
H8AB—C8A—H8AC | 109.5 | H8BB—C8B—H8BC | 109.5 |
C10A—C9A—N7A | 121.2 (5) | N7B—C9B—C10B | 121.3 (5) |
C10A—C9A—C14A | 117.6 (6) | N7B—C9B—C14B | 122.9 (5) |
N7A—C9A—C14A | 121.0 (5) | C10B—C9B—C14B | 115.8 (6) |
C11A—C10A—C9A | 121.3 (6) | C11B—C10B—C9B | 121.2 (6) |
C11A—C10A—H10A | 119.3 | C11B—C10B—H10B | 119.4 |
C9A—C10A—H10A | 119.3 | C9B—C10B—H10B | 119.4 |
C10A—C11A—C12A | 120.2 (6) | C12B—C11B—C10B | 122.2 (6) |
C10A—C11A—H11A | 119.9 | C12B—C11B—H11B | 118.9 |
C12A—C11A—H11A | 119.9 | C10B—C11B—H11B | 118.9 |
C13A—C12A—C11A | 119.3 (6) | C11B—C12B—C13B | 117.3 (6) |
C13A—C12A—H12A | 120.4 | C11B—C12B—H12B | 121.3 |
C11A—C12A—H12A | 120.4 | C13B—C12B—H12B | 121.3 |
C12A—C13A—C14A | 121.6 (6) | C14B—C13B—C12B | 121.6 (6) |
C12A—C13A—H13A | 119.2 | C14B—C13B—H13B | 119.2 |
C14A—C13A—H13A | 119.2 | C12B—C13B—H13B | 119.2 |
C13A—C14A—C9A | 119.9 (6) | C13B—C14B—C9B | 121.8 (6) |
C13A—C14A—H14A | 120.0 | C13B—C14B—H14B | 119.1 |
C9A—C14A—H14A | 120.0 | C9B—C14B—H14B | 119.1 |
O16A—C15A—C2A | 112.9 (4) | O16B—C15B—C2B | 112.7 (4) |
O16A—C15A—H15A | 109.0 | O16B—C15B—H15C | 109.0 |
C2A—C15A—H15A | 109.0 | C2B—C15B—H15C | 109.0 |
O16A—C15A—H15B | 109.0 | O16B—C15B—H15D | 109.0 |
C2A—C15A—H15B | 109.0 | C2B—C15B—H15D | 109.0 |
H15A—C15A—H15B | 107.8 | H15C—C15B—H15D | 107.8 |
C15A—O16A—C17A | 111.3 (4) | C15B—O16B—C17B | 111.5 (4) |
O16A—C17A—C18A | 112.8 (5) | O16B—C17B—C18B | 112.8 (4) |
O16A—C17A—H17A | 109.0 | O16B—C17B—H17C | 109.0 |
C18A—C17A—H17A | 109.0 | C18B—C17B—H17C | 109.0 |
O16A—C17A—H17B | 109.0 | O16B—C17B—H17D | 109.0 |
C18A—C17A—H17B | 109.0 | C18B—C17B—H17D | 109.0 |
H17A—C17A—H17B | 107.8 | H17C—C17B—H17D | 107.8 |
C23A—C18A—C19A | 116.6 (6) | C23B—C18B—C19B | 118.1 (5) |
C23A—C18A—C17A | 120.5 (6) | C23B—C18B—C17B | 119.7 (5) |
C19A—C18A—C17A | 122.9 (6) | C19B—C18B—C17B | 122.3 (5) |
C20A—C19A—C18A | 122.9 (6) | C20B—C19B—C18B | 120.8 (6) |
C20A—C19A—H19A | 118.6 | C20B—C19B—H19B | 119.6 |
C18A—C19A—H19A | 118.6 | C18B—C19B—H19B | 119.6 |
C19A—C20A—C21A | 118.7 (6) | C19B—C20B—C21B | 120.0 (6) |
C19A—C20A—H20A | 120.6 | C19B—C20B—H20B | 120.0 |
C21A—C20A—H20A | 120.6 | C21B—C20B—H20B | 120.0 |
O24A—C21A—C20A | 124.9 (7) | C22B—C21B—O24B | 115.7 (5) |
O24A—C21A—C22A | 115.5 (6) | C22B—C21B—C20B | 119.8 (6) |
C20A—C21A—C22A | 119.6 (6) | O24B—C21B—C20B | 124.5 (6) |
C23A—C22A—C21A | 120.4 (6) | C21B—C22B—C23B | 120.2 (6) |
C23A—C22A—H22A | 119.8 | C21B—C22B—H22B | 119.9 |
C21A—C22A—H22A | 119.8 | C23B—C22B—H22B | 119.9 |
C22A—C23A—C18A | 121.8 (6) | C22B—C23B—C18B | 121.1 (6) |
C22A—C23A—H23A | 119.1 | C22B—C23B—H23B | 119.4 |
C18A—C23A—H23A | 119.1 | C18B—C23B—H23B | 119.4 |
C21A—O24A—C25A | 117.9 (7) | C21B—O24B—C25B | 117.9 (5) |
O24A—C25A—H25A | 109.5 | O24B—C25B—H25D | 109.5 |
O24A—C25A—H25B | 109.5 | O24B—C25B—H25E | 109.5 |
H25A—C25A—H25B | 109.5 | H25D—C25B—H25E | 109.5 |
O24A—C25A—H25C | 109.5 | O24B—C25B—H25F | 109.5 |
H25A—C25A—H25C | 109.5 | H25D—C25B—H25F | 109.5 |
H25B—C25A—H25C | 109.5 | H25E—C25B—H25F | 109.5 |
O27A—C26A—C3A | 108.1 (5) | O27B—C26B—C3B | 107.6 (5) |
O27A—C26A—H26A | 110.1 | O27B—C26B—H26C | 110.2 |
C3A—C26A—H26A | 110.1 | C3B—C26B—H26C | 110.2 |
O27A—C26A—H26B | 110.1 | O27B—C26B—H26D | 110.2 |
C3A—C26A—H26B | 110.1 | C3B—C26B—H26D | 110.2 |
H26A—C26A—H26B | 108.4 | H26C—C26B—H26D | 108.5 |
C26A—O27A—C28A | 113.1 (5) | C28B—O27B—C26B | 112.7 (5) |
O27A—C28A—C29A | 114.1 (6) | O27B—C28B—C29B | 113.7 (5) |
O27A—C28A—H28A | 108.7 | O27B—C28B—H28C | 108.8 |
C29A—C28A—H28A | 108.7 | C29B—C28B—H28C | 108.8 |
O27A—C28A—H28B | 108.7 | O27B—C28B—H28D | 108.8 |
C29A—C28A—H28B | 108.7 | C29B—C28B—H28D | 108.8 |
H28A—C28A—H28B | 107.6 | H28C—C28B—H28D | 107.7 |
C34A—C29A—C30A | 117.9 (6) | C34B—C29B—C30B | 117.6 (6) |
C34A—C29A—C28A | 122.2 (6) | C34B—C29B—C28B | 123.0 (6) |
C30A—C29A—C28A | 119.9 (6) | C30B—C29B—C28B | 119.4 (6) |
C31A—C30A—C29A | 120.4 (7) | C31B—C30B—C29B | 121.3 (6) |
C31A—C30A—H30A | 119.8 | C31B—C30B—H30B | 119.3 |
C29A—C30A—H30A | 119.8 | C29B—C30B—H30B | 119.3 |
C30A—C31A—C32A | 121.6 (7) | C30B—C31B—C32B | 119.6 (6) |
C30A—C31A—H31A | 119.2 | C30B—C31B—H31B | 120.2 |
C32A—C31A—H31A | 119.2 | C32B—C31B—H31B | 120.2 |
O35A—C32A—C33A | 125.1 (6) | O35B—C32B—C33B | 124.6 (5) |
O35A—C32A—C31A | 116.0 (6) | O35B—C32B—C31B | 114.7 (5) |
C33A—C32A—C31A | 118.9 (6) | C33B—C32B—C31B | 120.6 (6) |
C32A—C33A—C34A | 119.2 (6) | C32B—C33B—C34B | 119.1 (5) |
C32A—C33A—H33A | 120.4 | C32B—C33B—H33B | 120.5 |
C34A—C33A—H33A | 120.4 | C34B—C33B—H33B | 120.5 |
C29A—C34A—C33A | 121.9 (6) | C29B—C34B—C33B | 121.7 (6) |
C29A—C34A—H34A | 119.0 | C29B—C34B—H34B | 119.1 |
C33A—C34A—H34A | 119.0 | C33B—C34B—H34B | 119.1 |
C32A—O35A—C36A | 117.0 (5) | C32B—O35B—C36B | 116.9 (5) |
O35A—C36A—H36A | 109.5 | O35B—C36B—H36D | 109.5 |
O35A—C36A—H36B | 109.5 | O35B—C36B—H36E | 109.5 |
H36A—C36A—H36B | 109.5 | H36D—C36B—H36E | 109.5 |
O35A—C36A—H36C | 109.5 | O35B—C36B—H36F | 109.5 |
H36A—C36A—H36C | 109.5 | H36D—C36B—H36F | 109.5 |
H36B—C36A—H36C | 109.5 | H36E—C36B—H36F | 109.5 |
C38A—O37A—C1A | 119.6 (4) | C38B—O37B—C1B | 118.0 (4) |
O39A—C38A—O37A | 123.1 (5) | O39B—C38B—O37B | 124.4 (5) |
O39A—C38A—C40A | 124.8 (5) | O39B—C38B—C40B | 125.0 (5) |
O37A—C38A—C40A | 112.1 (5) | O37B—C38B—C40B | 110.6 (5) |
C45A—C40A—C41A | 119.0 (5) | C41B—C40B—C45B | 120.2 (5) |
C45A—C40A—C38A | 119.9 (5) | C41B—C40B—C38B | 121.7 (5) |
C41A—C40A—C38A | 120.9 (5) | C45B—C40B—C38B | 118.1 (5) |
C42A—C41A—C40A | 120.1 (5) | C42B—C41B—C40B | 119.5 (5) |
C42A—C41A—H41A | 119.9 | C42B—C41B—H41B | 120.3 |
C40A—C41A—H41A | 119.9 | C40B—C41B—H41B | 120.3 |
C43A—C42A—C41A | 119.2 (6) | C43B—C42B—C41B | 119.5 (6) |
C43A—C42A—H42A | 120.4 | C43B—C42B—H42B | 120.2 |
C41A—C42A—H42A | 120.4 | C41B—C42B—H42B | 120.2 |
C42A—C43A—C44A | 121.6 (6) | C44B—C43B—C42B | 121.7 (6) |
C42A—C43A—Br1A | 118.5 (5) | C44B—C43B—Br1B | 120.0 (5) |
C44A—C43A—Br1A | 119.9 (5) | C42B—C43B—Br1B | 118.2 (5) |
C45A—C44A—C43A | 118.6 (6) | C43B—C44B—C45B | 119.5 (6) |
C45A—C44A—H44A | 120.7 | C43B—C44B—H44B | 120.3 |
C43A—C44A—H44A | 120.7 | C45B—C44B—H44B | 120.3 |
C44A—C45A—C40A | 121.4 (6) | C44B—C45B—C40B | 119.6 (6) |
C44A—C45A—H45A | 119.3 | C44B—C45B—H45B | 120.2 |
C40A—C45A—H45A | 119.3 | C40B—C45B—H45B | 120.2 |
O37A—C1A—C2A—C15A | −49.1 (6) | O37B—C1B—C2B—C15B | −48.4 (6) |
C6A—C1A—C2A—C15A | 69.9 (6) | C6B—C1B—C2B—C15B | 70.4 (6) |
O37A—C1A—C2A—C3A | −179.9 (4) | O37B—C1B—C2B—C3B | −179.2 (4) |
C6A—C1A—C2A—C3A | −60.9 (6) | C6B—C1B—C2B—C3B | −60.4 (6) |
C15A—C2A—C3A—C26A | 39.6 (7) | C15B—C2B—C3B—C4B | −88.0 (6) |
C1A—C2A—C3A—C26A | 169.2 (5) | C1B—C2B—C3B—C4B | 41.5 (6) |
C15A—C2A—C3A—C4A | −87.9 (6) | C15B—C2B—C3B—C26B | 39.7 (7) |
C1A—C2A—C3A—C4A | 41.7 (7) | C1B—C2B—C3B—C26B | 169.2 (5) |
C26A—C3A—C4A—C5A | −143.3 (6) | C26B—C3B—C4B—C5B | −143.0 (6) |
C2A—C3A—C4A—C5A | −15.0 (9) | C2B—C3B—C4B—C5B | −14.4 (8) |
C3A—C4A—C5A—C6A | 2.4 (10) | C3B—C4B—C5B—C6B | 2.0 (9) |
C4A—C5A—C6A—N7A | −143.2 (6) | C4B—C5B—C6B—N7B | −143.8 (6) |
C4A—C5A—C6A—C1A | −17.9 (8) | C4B—C5B—C6B—C1B | −18.1 (8) |
O37A—C1A—C6A—N7A | −65.0 (6) | O37B—C1B—C6B—N7B | −63.3 (6) |
C2A—C1A—C6A—N7A | 172.3 (5) | C2B—C1B—C6B—N7B | 173.7 (4) |
O37A—C1A—C6A—C5A | 170.8 (4) | O37B—C1B—C6B—C5B | 171.1 (4) |
C2A—C1A—C6A—C5A | 48.1 (6) | C2B—C1B—C6B—C5B | 48.1 (6) |
C5A—C6A—N7A—C9A | −147.0 (5) | C5B—C6B—N7B—C9B | −146.5 (5) |
C1A—C6A—N7A—C9A | 89.4 (6) | C1B—C6B—N7B—C9B | 89.1 (6) |
C5A—C6A—N7A—C8A | 63.9 (6) | C5B—C6B—N7B—C8B | 63.5 (6) |
C1A—C6A—N7A—C8A | −59.7 (6) | C1B—C6B—N7B—C8B | −60.9 (6) |
C8A—N7A—C9A—C10A | −1.6 (8) | C8B—N7B—C9B—C10B | −1.9 (8) |
C6A—N7A—C9A—C10A | −149.9 (5) | C6B—N7B—C9B—C10B | −150.7 (5) |
C8A—N7A—C9A—C14A | −177.3 (5) | C8B—N7B—C9B—C14B | −179.5 (5) |
C6A—N7A—C9A—C14A | 34.4 (7) | C6B—N7B—C9B—C14B | 31.7 (8) |
N7A—C9A—C10A—C11A | −175.9 (5) | N7B—C9B—C10B—C11B | −176.9 (6) |
C14A—C9A—C10A—C11A | 0.0 (8) | C14B—C9B—C10B—C11B | 0.9 (9) |
C9A—C10A—C11A—C12A | −1.3 (9) | C9B—C10B—C11B—C12B | 0.1 (10) |
C10A—C11A—C12A—C13A | 1.2 (10) | C10B—C11B—C12B—C13B | −0.7 (10) |
C11A—C12A—C13A—C14A | 0.2 (10) | C11B—C12B—C13B—C14B | 0.2 (10) |
C12A—C13A—C14A—C9A | −1.6 (9) | C12B—C13B—C14B—C9B | 0.8 (10) |
C10A—C9A—C14A—C13A | 1.5 (8) | N7B—C9B—C14B—C13B | 176.4 (6) |
N7A—C9A—C14A—C13A | 177.3 (5) | C10B—C9B—C14B—C13B | −1.4 (9) |
C1A—C2A—C15A—O16A | −71.4 (6) | C1B—C2B—C15B—O16B | −71.8 (6) |
C3A—C2A—C15A—O16A | 55.3 (7) | C3B—C2B—C15B—O16B | 54.9 (6) |
C2A—C15A—O16A—C17A | 171.0 (5) | C2B—C15B—O16B—C17B | 171.8 (4) |
C15A—O16A—C17A—C18A | −84.9 (6) | C15B—O16B—C17B—C18B | −84.8 (6) |
O16A—C17A—C18A—C23A | −93.2 (7) | O16B—C17B—C18B—C23B | −94.1 (6) |
O16A—C17A—C18A—C19A | 85.9 (7) | O16B—C17B—C18B—C19B | 84.5 (7) |
C23A—C18A—C19A—C20A | 1.6 (9) | C23B—C18B—C19B—C20B | 1.3 (9) |
C17A—C18A—C19A—C20A | −177.4 (6) | C17B—C18B—C19B—C20B | −177.4 (5) |
C18A—C19A—C20A—C21A | −0.7 (10) | C18B—C19B—C20B—C21B | 0.0 (9) |
C19A—C20A—C21A—O24A | 178.7 (6) | C19B—C20B—C21B—C22B | −1.5 (10) |
C19A—C20A—C21A—C22A | −1.1 (10) | C19B—C20B—C21B—O24B | 180.0 (6) |
O24A—C21A—C22A—C23A | −177.8 (6) | O24B—C21B—C22B—C23B | −179.6 (5) |
C20A—C21A—C22A—C23A | 2.1 (11) | C20B—C21B—C22B—C23B | 1.8 (10) |
C21A—C22A—C23A—C18A | −1.1 (11) | C21B—C22B—C23B—C18B | −0.4 (9) |
C19A—C18A—C23A—C22A | −0.7 (9) | C19B—C18B—C23B—C22B | −1.1 (9) |
C17A—C18A—C23A—C22A | 178.4 (6) | C17B—C18B—C23B—C22B | 177.6 (5) |
C20A—C21A—O24A—C25A | 4.9 (11) | C22B—C21B—O24B—C25B | −173.5 (6) |
C22A—C21A—O24A—C25A | −175.3 (7) | C20B—C21B—O24B—C25B | 5.1 (9) |
C4A—C3A—C26A—O27A | −178.1 (5) | C4B—C3B—C26B—O27B | −177.2 (4) |
C2A—C3A—C26A—O27A | 53.9 (7) | C2B—C3B—C26B—O27B | 54.0 (6) |
C3A—C26A—O27A—C28A | −174.6 (5) | C3B—C26B—O27B—C28B | −174.0 (5) |
C26A—O27A—C28A—C29A | −79.5 (7) | C26B—O27B—C28B—C29B | −80.1 (7) |
O27A—C28A—C29A—C34A | 99.7 (7) | O27B—C28B—C29B—C34B | 99.0 (7) |
O27A—C28A—C29A—C30A | −83.0 (7) | O27B—C28B—C29B—C30B | −83.7 (7) |
C34A—C29A—C30A—C31A | 2.4 (9) | C34B—C29B—C30B—C31B | 1.8 (9) |
C28A—C29A—C30A—C31A | −175.1 (6) | C28B—C29B—C30B—C31B | −175.6 (6) |
C29A—C30A—C31A—C32A | −0.5 (10) | C29B—C30B—C31B—C32B | −0.8 (10) |
C30A—C31A—C32A—O35A | 176.2 (6) | C30B—C31B—C32B—O35B | 176.3 (5) |
C30A—C31A—C32A—C33A | −3.0 (10) | C30B—C31B—C32B—C33B | −1.0 (10) |
O35A—C32A—C33A—C34A | −174.7 (5) | O35B—C32B—C33B—C34B | −175.3 (5) |
C31A—C32A—C33A—C34A | 4.4 (9) | C31B—C32B—C33B—C34B | 1.7 (9) |
C30A—C29A—C34A—C33A | −0.8 (9) | C30B—C29B—C34B—C33B | −1.1 (9) |
C28A—C29A—C34A—C33A | 176.5 (5) | C28B—C29B—C34B—C33B | 176.3 (6) |
C32A—C33A—C34A—C29A | −2.6 (9) | C32B—C33B—C34B—C29B | −0.6 (9) |
C33A—C32A—O35A—C36A | −6.7 (9) | C33B—C32B—O35B—C36B | −9.0 (8) |
C31A—C32A—O35A—C36A | 174.1 (6) | C31B—C32B—O35B—C36B | 173.8 (6) |
C6A—C1A—O37A—C38A | 154.5 (5) | C2B—C1B—O37B—C38B | −81.5 (6) |
C2A—C1A—O37A—C38A | −81.2 (6) | C6B—C1B—O37B—C38B | 154.7 (5) |
C1A—O37A—C38A—O39A | 8.3 (8) | C1B—O37B—C38B—O39B | 7.0 (8) |
C1A—O37A—C38A—C40A | −171.7 (4) | C1B—O37B—C38B—C40B | −172.6 (4) |
O39A—C38A—C40A—C45A | 6.1 (9) | O39B—C38B—C40B—C41B | −170.2 (6) |
O37A—C38A—C40A—C45A | −173.9 (5) | O37B—C38B—C40B—C41B | 9.4 (7) |
O39A—C38A—C40A—C41A | −169.4 (6) | O39B—C38B—C40B—C45B | 6.4 (9) |
O37A—C38A—C40A—C41A | 10.7 (7) | O37B—C38B—C40B—C45B | −174.0 (5) |
C45A—C40A—C41A—C42A | −0.2 (8) | C45B—C40B—C41B—C42B | −1.5 (9) |
C38A—C40A—C41A—C42A | 175.3 (5) | C38B—C40B—C41B—C42B | 175.1 (5) |
C40A—C41A—C42A—C43A | −0.4 (9) | C40B—C41B—C42B—C43B | 2.3 (9) |
C41A—C42A—C43A—C44A | 1.4 (9) | C41B—C42B—C43B—C44B | −1.7 (9) |
C41A—C42A—C43A—Br1A | −179.9 (4) | C41B—C42B—C43B—Br1B | 179.1 (5) |
C42A—C43A—C44A—C45A | −1.9 (9) | C42B—C43B—C44B—C45B | 0.3 (10) |
Br1A—C43A—C44A—C45A | 179.5 (5) | Br1B—C43B—C44B—C45B | 179.4 (5) |
C43A—C44A—C45A—C40A | 1.4 (9) | C43B—C44B—C45B—C40B | 0.5 (9) |
C41A—C40A—C45A—C44A | −0.3 (8) | C41B—C40B—C45B—C44B | 0.1 (9) |
C38A—C40A—C45A—C44A | −175.9 (5) | C38B—C40B—C45B—C44B | −176.6 (5) |
Experimental details
Crystal data | |
Chemical formula | C38H40BrNO6 |
Mr | 686.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 7.8180 (2), 11.2850 (3), 18.6830 (5) |
α, β, γ (°) | 90.906 (1), 91.9660 (11), 90.0940 (14) |
V (Å3) | 1647.15 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.30 |
Crystal size (mm) | 0.26 × 0.12 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.729, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19157, 10534, 8339 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.150, 1.03 |
No. of reflections | 10534 |
No. of parameters | 836 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.85, −0.41 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.010 (9) |
Computer programs: COLLECT (Nonius, 1997-2001), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1999), SHELXTL.
C1A—C2A | 1.528 (7) | C1B—C2B | 1.530 (7) |
C2A—C3A | 1.555 (8) | C2B—C3B | 1.544 (7) |
C3A—C4A | 1.512 (8) | C3B—C4B | 1.512 (8) |
C4A—C5A | 1.324 (9) | C4B—C5B | 1.323 (9) |
C5A—C6A | 1.509 (8) | C5B—C6B | 1.507 (8) |
C6A—N7A | 1.464 (7) | C6B—N7B | 1.471 (7) |
N7A—C9A | 1.409 (7) | N7B—C9B | 1.385 (7) |
C6A—C1A—C2A | 114.2 (5) | C2B—C1B—C6B | 113.6 (4) |
C1A—C2A—C3A | 108.1 (4) | C1B—C2B—C3B | 108.2 (4) |
C4A—C3A—C2A | 112.6 (5) | C4B—C3B—C2B | 113.3 (5) |
C5A—C4A—C3A | 124.6 (6) | C5B—C4B—C3B | 124.5 (5) |
C4A—C5A—C6A | 123.3 (6) | C4B—C5B—C6B | 123.3 (5) |
C5A—C6A—C1A | 109.8 (5) | C5B—C6B—C1B | 109.9 (5) |
C9A—N7A—C8A | 117.7 (5) | C9B—N7B—C8B | 118.2 (5) |
C9A—N7A—C6A | 120.0 (5) | C9B—N7B—C6B | 120.8 (5) |
C8A—N7A—C6A | 114.8 (5) | C8B—N7B—C6B | 114.0 (5) |
C6A—N7A—C9A—C10A | −149.9 (5) | C6B—N7B—C9B—C10B | −150.7 (5) |
C1A—C2A—C15A—O16A | −71.4 (6) | C1B—C2B—C15B—O16B | −71.8 (6) |
O16A—C17A—C18A—C19A | 85.9 (7) | O16B—C17B—C18B—C19B | 84.5 (7) |
C2A—C3A—C26A—O27A | 53.9 (7) | C2B—C3B—C26B—O27B | 54.0 (6) |
O27A—C28A—C29A—C30A | −83.0 (7) | O27B—C28B—C29B—C30B | −83.7 (7) |
C1A—O37A—C38A—C40A | −171.7 (4) | C1B—O37B—C38B—C40B | −172.6 (4) |
O37A—C38A—C40A—C41A | 10.7 (7) | O37B—C38B—C40B—C41B | 9.4 (7) |
Recently, we reported a new rhodium-catalyzed ring opening reaction of a variety of oxabicyclic alkenes with a wide range of nucleophiles (Lautens & Fagnou, 2001). In particular, we found that N-methylaniline could be used to induce the enantioselective ring opening of 5,6-bis(4-methoxybenzyloxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene. The 1,2-regio-, trans and relative stereochemistry, as well as the absolute stereochemistry, for this reaction were established by the X-ray diffraction analysis of the title compound, (I), when (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine [(R)-(S)-PPF-PtBu2] is used as the chiral ligand.
There are two independent molecules (A and B) in the asymmetric unit of the structure (see Figs. 1 and 2). An analysis (Cremer & Pople, 1975) of the puckering of the central cyclohexene ring (C1–C6) gives the total puckering amplitudes QT = 0.478 (6) Å for molecule A and QT = 0.480 (6) Å for molecule B. The conformation analysis of that ring (Duax et al., 1976) shows that the conformation is a half-chair, with a local pseudo-twofold axis running along the midpoints of the C1—C2 and C4—C5 bonds in both molecules.