organic compounds
The synthesis of (1SR,2SR,5RS,6RS)-5-ethyl-4-(4-methoxyphenyl)-2,6-dimethyl-3-cyclohexenecarboxylic acid was accompanied by the formation of a by-product shown to differ only by the absence of the 5-ethyl group. That mixture was subjected to an enantiomer resolution process utilizing (-)-menthol and dicyclohexylcarbodiimide (DCC), and the expected diastereomers of both compounds were formed along with their anhydrides and an unexpected, but related, compound in both cases. The unexpected compound formed from the substrate lacking the 5-ethyl group was unequivocally identified by X-ray analysis as the title compound, C29H42N2O3, (I), a result that, together with the NMR spectra, similarly identified the corresponding product from the compound possessing the 5-ethyl substituent. The two enantiomers of (I) appear to be disordered and superimposed in the asymmetric unit, differing only in the position of the double bond, a rare phenomenon made possible by the unusual stereochemistry of (I).
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016800/hg6067sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016800/hg6067Isup2.hkl |
CCDC reference: 248809
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2003).
N,N'-Dicyclohexyl-N-[(1RS,2RS,6SR)-4-(4-methoxyphenyl)-2,6-dimethyl-3- cyclohexene-1-carbonyl]urea top
Crystal data top
C29H42N2O3 | F(000) = 1016 |
Mr = 466.65 | Dx = 1.168 Mg m−3 |
Monoclinic, P21/n | Melting point = 534–535 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.0059 (3) Å | Cell parameters from 9091 reflections |
b = 10.4719 (2) Å | θ = 2.3–29.2° |
c = 16.9266 (3) Å | µ = 0.08 mm−1 |
β = 93.547 (1)° | T = 155 K |
V = 2654.76 (9) Å3 | Prism, colorless |
Z = 4 | 0.50 × 0.35 × 0.19 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3507 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
φ and ω scans | h = −17→17 |
17643 measured reflections | k = −12→12 |
4675 independent reflections | l = −20→20 |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.232 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1585P)2 + 0.2847P] where P = (Fo2 + 2Fc2)/3 |
4675 reflections | (Δ/σ)max < 0.001 |
310 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.04040 (11) | 0.23823 (19) | 0.33237 (9) | 0.0574 (5) | |
O2 | 0.22702 (10) | 0.51170 (15) | 0.26003 (8) | 0.0444 (4) | |
O3 | 0.28531 (11) | 0.40887 (17) | 0.91034 (9) | 0.0520 (5) | |
N1 | 0.15485 (11) | 0.31537 (17) | 0.26599 (9) | 0.0371 (4) | |
N2 | 0.30937 (11) | 0.32926 (18) | 0.26929 (10) | 0.0408 (5) | |
C1 | 0.16144 (13) | 0.3261 (2) | 0.41322 (12) | 0.0398 (5) | |
C2 | 0.17717 (15) | 0.2055 (2) | 0.46376 (12) | 0.0410 (5) | |
C3 | 0.2101 (2) | 0.2385 (3) | 0.54641 (15) | 0.0704 (9) | |
C4 | 0.19029 (13) | 0.3526 (2) | 0.58292 (12) | 0.0383 (5) | |
C5 | 0.14551 (18) | 0.4498 (3) | 0.53801 (14) | 0.0604 (7) | |
C6 | 0.10474 (14) | 0.4239 (2) | 0.45619 (13) | 0.0424 (5) | |
C7 | 0.09130 (16) | 0.5470 (2) | 0.40950 (14) | 0.0529 (6) | |
C8 | 0.24044 (19) | 0.1125 (3) | 0.42687 (14) | 0.0601 (7) | |
C9 | 0.11367 (14) | 0.2911 (2) | 0.33430 (13) | 0.0420 (5) | |
C10 | 0.21756 (13) | 0.3708 (2) | 0.66812 (12) | 0.0370 (5) | |
C11 | 0.16804 (14) | 0.4461 (2) | 0.71823 (12) | 0.0405 (5) | |
C12 | 0.19277 (14) | 0.4559 (2) | 0.79784 (13) | 0.0415 (5) | |
C13 | 0.26664 (15) | 0.3924 (2) | 0.83071 (12) | 0.0416 (5) | |
C14 | 0.31787 (15) | 0.3189 (2) | 0.78234 (13) | 0.0431 (5) | |
C15 | 0.29212 (14) | 0.3097 (2) | 0.70259 (12) | 0.0404 (5) | |
C16 | 0.36064 (19) | 0.3430 (3) | 0.94548 (16) | 0.0682 (8) | |
C17 | 0.23299 (13) | 0.3955 (2) | 0.26552 (11) | 0.0368 (5) | |
C18 | 0.10785 (14) | 0.2857 (2) | 0.18839 (12) | 0.0409 (5) | |
C19 | 0.17369 (15) | 0.2556 (2) | 0.12637 (13) | 0.0476 (6) | |
C20 | 0.12490 (18) | 0.2238 (3) | 0.04667 (14) | 0.0587 (7) | |
C21 | 0.06166 (18) | 0.3295 (3) | 0.02035 (14) | 0.0608 (7) | |
C22 | −0.00484 (17) | 0.3554 (3) | 0.08266 (15) | 0.0606 (7) | |
C23 | 0.04337 (16) | 0.3909 (3) | 0.16145 (14) | 0.0529 (6) | |
C24 | 0.39730 (13) | 0.3889 (2) | 0.26933 (12) | 0.0395 (5) | |
C25 | 0.45302 (18) | 0.3252 (3) | 0.20933 (18) | 0.0731 (9) | |
C26 | 0.54506 (19) | 0.3869 (4) | 0.2099 (2) | 0.0880 (12) | |
C27 | 0.59217 (18) | 0.3798 (3) | 0.2910 (3) | 0.0853 (11) | |
C28 | 0.53638 (17) | 0.4450 (3) | 0.35186 (17) | 0.0678 (8) | |
C29 | 0.44327 (17) | 0.3871 (3) | 0.35103 (15) | 0.0615 (7) | |
H1 | 0.2204 | 0.3655 | 0.4033 | 0.048* | |
H2 | 0.1183 | 0.1615 | 0.4667 | 0.049* | |
H2A | 0.3065 | 0.2455 | 0.2719 | 0.049* | |
H3 | 0.2463 | 0.1781 | 0.5754 | 0.084* | |
H5A | 0.1884 | 0.5208 | 0.5334 | 0.072* | |
H5B | 0.0971 | 0.4821 | 0.5699 | 0.072* | |
H6 | 0.0446 | 0.3851 | 0.4619 | 0.051* | |
H7A | 0.0539 | 0.6055 | 0.4383 | 0.079* | |
H7B | 0.0619 | 0.5281 | 0.3575 | 0.079* | |
H7C | 0.1494 | 0.5870 | 0.4026 | 0.079* | |
H8A | 0.2980 | 0.1544 | 0.4209 | 0.090* | |
H8B | 0.2149 | 0.0857 | 0.3748 | 0.090* | |
H8C | 0.2492 | 0.0376 | 0.4612 | 0.090* | |
H11 | 0.1169 | 0.4909 | 0.6970 | 0.049* | |
H12 | 0.1583 | 0.5073 | 0.8307 | 0.050* | |
H14 | 0.3696 | 0.2758 | 0.8036 | 0.052* | |
H15 | 0.3273 | 0.2591 | 0.6699 | 0.048* | |
H16A | 0.3532 | 0.2510 | 0.9367 | 0.102* | |
H16B | 0.3658 | 0.3605 | 1.0025 | 0.102* | |
H16C | 0.4148 | 0.3722 | 0.9215 | 0.102* | |
H18 | 0.0717 | 0.2069 | 0.1957 | 0.049* | |
H19A | 0.2113 | 0.1822 | 0.1443 | 0.057* | |
H19B | 0.2133 | 0.3301 | 0.1200 | 0.057* | |
H20A | 0.1691 | 0.2110 | 0.0063 | 0.070* | |
H20B | 0.0911 | 0.1433 | 0.0515 | 0.070* | |
H21A | 0.0291 | 0.3052 | −0.0301 | 0.073* | |
H21B | 0.0960 | 0.4082 | 0.0110 | 0.073* | |
H22A | −0.0418 | 0.2784 | 0.0896 | 0.073* | |
H22B | −0.0450 | 0.4260 | 0.0647 | 0.073* | |
H23A | 0.0765 | 0.4718 | 0.1556 | 0.064* | |
H23B | −0.0008 | 0.4041 | 0.2018 | 0.064* | |
H24 | 0.3886 | 0.4802 | 0.2532 | 0.047* | |
H25A | 0.4227 | 0.3331 | 0.1559 | 0.088* | |
H25B | 0.4594 | 0.2333 | 0.2219 | 0.088* | |
H26A | 0.5813 | 0.3428 | 0.1712 | 0.106* | |
H26B | 0.5387 | 0.4774 | 0.1936 | 0.106* | |
H27A | 0.6511 | 0.4221 | 0.2902 | 0.102* | |
H27B | 0.6021 | 0.2893 | 0.3059 | 0.102* | |
H28A | 0.5664 | 0.4354 | 0.4053 | 0.081* | |
H28B | 0.5317 | 0.5373 | 0.3398 | 0.081* | |
H29A | 0.4477 | 0.2978 | 0.3701 | 0.074* | |
H29B | 0.4070 | 0.4356 | 0.3877 | 0.074* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0483 (10) | 0.0770 (13) | 0.0468 (10) | −0.0215 (9) | 0.0016 (7) | 0.0073 (8) |
O2 | 0.0466 (9) | 0.0388 (10) | 0.0483 (9) | −0.0029 (7) | 0.0064 (7) | 0.0032 (7) |
O3 | 0.0629 (10) | 0.0551 (10) | 0.0372 (9) | 0.0108 (8) | −0.0030 (7) | −0.0052 (7) |
N1 | 0.0359 (9) | 0.0398 (10) | 0.0355 (9) | −0.0042 (7) | 0.0011 (7) | 0.0029 (8) |
N2 | 0.0359 (9) | 0.0402 (11) | 0.0462 (10) | −0.0035 (8) | 0.0014 (7) | 0.0031 (8) |
C1 | 0.0377 (11) | 0.0447 (13) | 0.0375 (11) | −0.0032 (9) | 0.0060 (9) | 0.0035 (9) |
C2 | 0.0466 (12) | 0.0407 (12) | 0.0361 (11) | −0.0010 (10) | 0.0050 (9) | 0.0015 (9) |
C3 | 0.125 (3) | 0.0434 (15) | 0.0404 (14) | 0.0207 (16) | −0.0129 (14) | 0.0000 (11) |
C4 | 0.0368 (11) | 0.0414 (12) | 0.0373 (11) | −0.0019 (9) | 0.0068 (9) | 0.0031 (9) |
C5 | 0.0672 (16) | 0.0635 (18) | 0.0490 (14) | 0.0248 (13) | −0.0085 (12) | −0.0095 (12) |
C6 | 0.0385 (11) | 0.0472 (14) | 0.0420 (12) | 0.0030 (10) | 0.0062 (9) | 0.0049 (10) |
C7 | 0.0511 (14) | 0.0562 (16) | 0.0528 (14) | 0.0111 (11) | 0.0133 (11) | 0.0089 (12) |
C8 | 0.0843 (19) | 0.0508 (16) | 0.0467 (14) | 0.0190 (13) | 0.0163 (12) | 0.0075 (11) |
C9 | 0.0388 (12) | 0.0452 (13) | 0.0420 (12) | −0.0050 (10) | 0.0028 (9) | 0.0045 (10) |
C10 | 0.0358 (11) | 0.0355 (12) | 0.0402 (12) | −0.0023 (9) | 0.0056 (9) | 0.0000 (9) |
C11 | 0.0396 (11) | 0.0386 (13) | 0.0433 (12) | 0.0031 (9) | 0.0022 (9) | −0.0023 (9) |
C12 | 0.0431 (12) | 0.0386 (12) | 0.0432 (12) | 0.0042 (9) | 0.0065 (9) | −0.0063 (10) |
C13 | 0.0477 (12) | 0.0405 (13) | 0.0365 (11) | −0.0015 (10) | 0.0018 (9) | −0.0030 (9) |
C14 | 0.0442 (12) | 0.0393 (13) | 0.0455 (12) | 0.0046 (10) | 0.0012 (9) | −0.0003 (10) |
C15 | 0.0424 (12) | 0.0390 (13) | 0.0403 (12) | 0.0050 (9) | 0.0072 (9) | −0.0019 (10) |
C16 | 0.0789 (19) | 0.075 (2) | 0.0494 (15) | 0.0267 (16) | −0.0103 (13) | −0.0035 (13) |
C17 | 0.0392 (11) | 0.0409 (13) | 0.0305 (10) | −0.0026 (9) | 0.0041 (8) | 0.0006 (9) |
C18 | 0.0432 (12) | 0.0407 (13) | 0.0381 (12) | −0.0067 (9) | −0.0032 (9) | 0.0009 (9) |
C19 | 0.0496 (13) | 0.0489 (14) | 0.0439 (13) | 0.0007 (11) | 0.0009 (10) | −0.0020 (10) |
C20 | 0.0668 (16) | 0.0678 (18) | 0.0412 (13) | −0.0049 (14) | 0.0010 (11) | −0.0090 (12) |
C21 | 0.0678 (17) | 0.0743 (19) | 0.0388 (13) | −0.0081 (14) | −0.0093 (11) | 0.0026 (12) |
C22 | 0.0534 (15) | 0.0731 (19) | 0.0532 (15) | 0.0050 (13) | −0.0139 (12) | 0.0065 (13) |
C23 | 0.0484 (14) | 0.0639 (17) | 0.0457 (13) | 0.0105 (12) | −0.0032 (10) | −0.0020 (12) |
C24 | 0.0348 (11) | 0.0404 (13) | 0.0432 (12) | −0.0040 (9) | 0.0021 (9) | −0.0005 (9) |
C25 | 0.0599 (16) | 0.085 (2) | 0.0776 (19) | −0.0213 (15) | 0.0268 (14) | −0.0343 (16) |
C26 | 0.0579 (18) | 0.102 (3) | 0.109 (3) | −0.0275 (17) | 0.0443 (18) | −0.047 (2) |
C27 | 0.0412 (15) | 0.0445 (17) | 0.169 (4) | 0.0019 (12) | 0.0005 (18) | −0.0034 (19) |
C28 | 0.0520 (15) | 0.077 (2) | 0.0722 (18) | −0.0138 (14) | −0.0187 (13) | 0.0128 (15) |
C29 | 0.0525 (15) | 0.079 (2) | 0.0515 (15) | −0.0134 (13) | −0.0082 (11) | 0.0090 (13) |
Geometric parameters (Å, º) top
C1—C2 | 1.535 (3) | C5—H5A | 0.9900 |
C2—C3 | 1.495 (3) | C5—H5B | 0.9900 |
C3—C4 | 1.386 (3) | C3—H3 | 0.9500 |
C4—C5 | 1.415 (3) | C2—H2 | 1.0000 |
C5—C6 | 1.504 (3) | C7—H7A | 0.9800 |
C1—C6 | 1.542 (3) | C7—H7B | 0.9800 |
C2—C8 | 1.521 (3) | C7—H7C | 0.9800 |
C6—C7 | 1.520 (3) | C8—H8A | 0.9800 |
O1—C9 | 1.230 (3) | C8—H8B | 0.9800 |
O2—C17 | 1.223 (3) | C8—H8C | 0.9800 |
O3—C13 | 1.370 (2) | C11—H11 | 0.9500 |
O3—C16 | 1.423 (3) | C12—H12 | 0.9500 |
N1—C9 | 1.368 (3) | C14—H14 | 0.9500 |
N1—C17 | 1.442 (3) | C15—H15 | 0.9500 |
N1—C18 | 1.485 (3) | C16—H16A | 0.9800 |
N2—C17 | 1.338 (3) | C16—H16B | 0.9800 |
N2—C24 | 1.460 (3) | C16—H16C | 0.9800 |
C1—C9 | 1.521 (3) | C18—H18 | 1.0000 |
C4—C10 | 1.487 (3) | C19—H19A | 0.9900 |
C10—C15 | 1.386 (3) | C19—H19B | 0.9900 |
C10—C11 | 1.404 (3) | C20—H20A | 0.9900 |
C11—C12 | 1.379 (3) | C20—H20B | 0.9900 |
C12—C13 | 1.380 (3) | C21—H21A | 0.9900 |
C13—C14 | 1.390 (3) | C21—H21B | 0.9900 |
C14—C15 | 1.384 (3) | C22—H22A | 0.9900 |
C18—C23 | 1.517 (3) | C22—H22B | 0.9900 |
C18—C19 | 1.518 (3) | C23—H23A | 0.9900 |
C19—C20 | 1.531 (3) | C23—H23B | 0.9900 |
C20—C21 | 1.507 (4) | C24—H24 | 1.0000 |
C21—C22 | 1.520 (4) | C25—H25A | 0.9900 |
C22—C23 | 1.523 (3) | C25—H25B | 0.9900 |
C24—C29 | 1.507 (3) | C26—H26A | 0.9900 |
C24—C25 | 1.510 (3) | C26—H26B | 0.9900 |
C25—C26 | 1.524 (4) | C27—H27A | 0.9900 |
C26—C27 | 1.507 (5) | C27—H27B | 0.9900 |
C27—C28 | 1.529 (5) | C28—H28A | 0.9900 |
C28—C29 | 1.522 (3) | C28—H28B | 0.9900 |
N2—H2A | 0.8800 | C29—H29A | 0.9900 |
C1—H1 | 1.0000 | C29—H29B | 0.9900 |
C6—H6 | 1.0000 | ||
C1—C2—C3 | 111.22 (19) | C2—C8—H8C | 109.5 |
C2—C3—C4 | 123.3 (2) | H8A—C8—H8C | 109.5 |
C3—C4—C5 | 119.2 (2) | H8B—C8—H8C | 109.5 |
C4—C5—C6 | 121.2 (2) | C4—C3—H3 | 118.3 |
C5—C6—C1 | 110.46 (18) | C2—C3—H3 | 118.3 |
C6—C1—C2 | 110.71 (17) | C12—C11—H11 | 119.6 |
C5—C6—C7 | 111.0 (2) | C10—C11—H11 | 119.6 |
C1—C6—C7 | 112.18 (18) | C11—C12—H12 | 119.4 |
C3—C2—C8 | 110.7 (2) | C13—C12—H12 | 119.4 |
C1—C2—C8 | 112.11 (18) | C15—C14—H14 | 120.6 |
C13—O3—C16 | 117.33 (18) | C13—C14—H14 | 120.6 |
C9—N1—C17 | 121.50 (16) | C14—C15—H15 | 118.4 |
C9—N1—C18 | 119.62 (17) | C10—C15—H15 | 118.4 |
C17—N1—C18 | 117.29 (15) | O3—C16—H16A | 109.5 |
C17—N2—C24 | 123.33 (19) | O3—C16—H16B | 109.5 |
C9—C1—C2 | 109.81 (19) | H16A—C16—H16B | 109.5 |
C9—C1—C6 | 109.29 (17) | O3—C16—H16C | 109.5 |
C3—C4—C10 | 119.3 (2) | H16A—C16—H16C | 109.5 |
C5—C4—C10 | 121.5 (2) | H16B—C16—H16C | 109.5 |
O1—C9—N1 | 120.7 (2) | N1—C18—H18 | 107.2 |
O1—C9—C1 | 120.25 (19) | C23—C18—H18 | 107.2 |
N1—C9—C1 | 118.98 (18) | C19—C18—H18 | 107.2 |
C15—C10—C11 | 116.65 (19) | C18—C19—H19A | 109.4 |
C15—C10—C4 | 121.06 (19) | C20—C19—H19A | 109.4 |
C11—C10—C4 | 122.25 (19) | C18—C19—H19B | 109.4 |
C12—C11—C10 | 120.7 (2) | C20—C19—H19B | 109.4 |
C11—C12—C13 | 121.3 (2) | H19A—C19—H19B | 108.0 |
O3—C13—C12 | 116.51 (19) | C21—C20—H20A | 109.4 |
O3—C13—C14 | 124.2 (2) | C19—C20—H20A | 109.4 |
C12—C13—C14 | 119.3 (2) | C21—C20—H20B | 109.4 |
C15—C14—C13 | 118.8 (2) | C19—C20—H20B | 109.4 |
C14—C15—C10 | 123.22 (19) | H20A—C20—H20B | 108.0 |
O2—C17—N2 | 125.32 (19) | C20—C21—H21A | 109.5 |
O2—C17—N1 | 121.57 (19) | C22—C21—H21A | 109.5 |
N2—C17—N1 | 113.09 (19) | C20—C21—H21B | 109.5 |
N1—C18—C23 | 111.92 (18) | C22—C21—H21B | 109.5 |
N1—C18—C19 | 111.18 (17) | H21A—C21—H21B | 108.1 |
C23—C18—C19 | 111.89 (18) | C21—C22—H22A | 109.5 |
C18—C19—C20 | 110.99 (19) | C23—C22—H22A | 109.5 |
C21—C20—C19 | 111.0 (2) | C21—C22—H22B | 109.5 |
C20—C21—C22 | 110.7 (2) | C23—C22—H22B | 109.5 |
C21—C22—C23 | 110.7 (2) | H22A—C22—H22B | 108.1 |
C18—C23—C22 | 110.2 (2) | C18—C23—H23A | 109.6 |
N2—C24—C29 | 110.93 (17) | C22—C23—H23A | 109.6 |
N2—C24—C25 | 110.40 (19) | C18—C23—H23B | 109.6 |
C29—C24—C25 | 111.7 (2) | C22—C23—H23B | 109.6 |
C24—C25—C26 | 110.4 (2) | H23A—C23—H23B | 108.1 |
C27—C26—C25 | 111.0 (3) | N2—C24—H24 | 107.9 |
C26—C27—C28 | 110.3 (2) | C29—C24—H24 | 107.9 |
C29—C28—C27 | 110.9 (2) | C25—C24—H24 | 107.9 |
C24—C29—C28 | 111.8 (2) | C24—C25—H25A | 109.6 |
C17—N2—H2A | 118.3 | C26—C25—H25A | 109.6 |
C24—N2—H2A | 118.3 | C24—C25—H25B | 109.6 |
C9—C1—H1 | 109.0 | C26—C25—H25B | 109.6 |
C2—C1—H1 | 109.0 | H25A—C25—H25B | 108.1 |
C6—C1—H1 | 109.0 | C27—C26—H26A | 109.4 |
C5—C6—H6 | 107.7 | C25—C26—H26A | 109.4 |
C7—C6—H6 | 107.7 | C27—C26—H26B | 109.4 |
C1—C6—H6 | 107.7 | C25—C26—H26B | 109.4 |
C4—C5—H5A | 107.0 | H26A—C26—H26B | 108.0 |
C6—C5—H5A | 107.0 | C26—C27—H27A | 109.6 |
C4—C5—H5B | 107.0 | C28—C27—H27A | 109.6 |
C6—C5—H5B | 107.0 | C26—C27—H27B | 109.6 |
H5A—C5—H5B | 106.8 | C28—C27—H27B | 109.6 |
C3—C2—H2 | 107.5 | H27A—C27—H27B | 108.1 |
C8—C2—H2 | 107.5 | C29—C28—H28A | 109.5 |
C1—C2—H2 | 107.5 | C27—C28—H28A | 109.5 |
C6—C7—H7A | 109.5 | C29—C28—H28B | 109.5 |
C6—C7—H7B | 109.5 | C27—C28—H28B | 109.5 |
H7A—C7—H7B | 109.5 | H28A—C28—H28B | 108.1 |
C6—C7—H7C | 109.5 | C24—C29—H29A | 109.3 |
H7A—C7—H7C | 109.5 | C28—C29—H29A | 109.3 |
H7B—C7—H7C | 109.5 | C24—C29—H29B | 109.3 |
C2—C8—H8A | 109.5 | C28—C29—H29B | 109.3 |
C2—C8—H8B | 109.5 | H29A—C29—H29B | 107.9 |
H8A—C8—H8B | 109.5 | ||
C9—C1—C6—C5 | 174.05 (19) | C11—C12—C13—C14 | 1.0 (3) |
C2—C1—C6—C5 | 53.0 (3) | O3—C13—C14—C15 | −180.0 (2) |
C9—C1—C6—C7 | −61.5 (2) | C12—C13—C14—C15 | −1.2 (3) |
C2—C1—C6—C7 | 177.42 (18) | C13—C14—C15—C10 | 0.2 (3) |
C7—C6—C5—C4 | −159.4 (2) | C11—C10—C15—C14 | 0.9 (3) |
C1—C6—C5—C4 | −34.3 (3) | C4—C10—C15—C14 | −177.0 (2) |
C6—C5—C4—C3 | 11.0 (4) | C24—N2—C17—O2 | 1.6 (3) |
C6—C5—C4—C10 | −169.8 (2) | C24—N2—C17—N1 | 179.74 (16) |
C5—C4—C3—C2 | −7.5 (4) | C9—N1—C17—O2 | −85.3 (3) |
C10—C4—C3—C2 | 173.2 (2) | C18—N1—C17—O2 | 80.3 (2) |
C4—C3—C2—C8 | 153.1 (3) | C9—N1—C17—N2 | 96.5 (2) |
C4—C3—C2—C1 | 27.8 (4) | C18—N1—C17—N2 | −97.9 (2) |
C9—C1—C2—C3 | −170.6 (2) | C9—N1—C18—C23 | 82.3 (2) |
C6—C1—C2—C3 | −49.8 (3) | C17—N1—C18—C23 | −83.6 (2) |
C9—C1—C2—C8 | 64.9 (2) | C9—N1—C18—C19 | −151.8 (2) |
C6—C1—C2—C8 | −174.35 (19) | C17—N1—C18—C19 | 42.3 (3) |
C17—N1—C9—O1 | 169.5 (2) | N1—C18—C19—C20 | 179.4 (2) |
C18—N1—C9—O1 | 4.3 (3) | C23—C18—C19—C20 | −54.6 (3) |
C17—N1—C9—C1 | −12.7 (3) | C18—C19—C20—C21 | 54.9 (3) |
C18—N1—C9—C1 | −177.98 (19) | C19—C20—C21—C22 | −56.8 (3) |
C2—C1—C9—O1 | 58.9 (3) | C20—C21—C22—C23 | 58.2 (3) |
C6—C1—C9—O1 | −62.7 (3) | N1—C18—C23—C22 | −178.74 (19) |
C2—C1—C9—N1 | −118.9 (2) | C19—C18—C23—C22 | 55.7 (3) |
C6—C1—C9—N1 | 119.5 (2) | C21—C22—C23—C18 | −57.1 (3) |
C3—C4—C10—C15 | 29.2 (3) | C17—N2—C24—C29 | 104.6 (2) |
C5—C4—C10—C15 | −150.0 (2) | C17—N2—C24—C25 | −131.0 (2) |
C3—C4—C10—C11 | −148.5 (3) | N2—C24—C25—C26 | −179.6 (3) |
C5—C4—C10—C11 | 32.3 (3) | C29—C24—C25—C26 | −55.6 (3) |
C15—C10—C11—C12 | −1.0 (3) | C24—C25—C26—C27 | 57.7 (4) |
C4—C10—C11—C12 | 176.76 (19) | C25—C26—C27—C28 | −57.9 (4) |
C10—C11—C12—C13 | 0.1 (3) | C26—C27—C28—C29 | 55.9 (3) |
C16—O3—C13—C12 | 179.3 (2) | N2—C24—C29—C28 | 178.1 (2) |
C16—O3—C13—C14 | −1.9 (3) | C25—C24—C29—C28 | 54.5 (3) |
C11—C12—C13—O3 | 179.89 (19) | C27—C28—C29—C24 | −54.3 (3) |