Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101001767/na1501sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001767/na1501IIsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001767/na1501IIIsup3.hkl |
CCDC references: 163949; 163950
For both compounds, data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS. Program(s) used to solve structure: SIR92 (Altomare et al. 1994) for (II); SIR92 (Altomare et al., 1994) for (III). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARSTCIF (Nardelli, 1991) for (II); SHELXL97 for (III).
C18H26O3 | Dx = 1.260 Mg m−3 |
Mr = 290.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 52 reflections |
a = 6.5843 (5) Å | θ = 5.2–14.8° |
b = 10.4040 (7) Å | µ = 0.08 mm−1 |
c = 22.3443 (12) Å | T = 293 K |
V = 1530.65 (18) Å3 | Cubic, colourless |
Z = 4 | 0.32 × 0.30 × 0.30 mm |
F(000) = 632 |
Bruker P4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 1.8° |
Graphite monochromator | h = 0→9 |
2θ/ω scans | k = 0→14 |
5088 measured reflections | l = 0→31 |
2577 independent reflections | 3 standard reflections every 197 reflections |
2216 reflections with I > 2σ(I) | intensity decay: 0.0% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.086 | (Δ/σ)max = 0.014 |
S = 0.98 | Δρmax = 0.24 e Å−3 |
2577 reflections | Δρmin = −0.13 e Å−3 |
295 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0151 (19) |
Primary atom site location: structure-invariant direct methods | Absolute structure: based on the reagents configuration |
Secondary atom site location: difference Fourier map |
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. Ring puckering coordinates following Cremer D. & Pople J·A., JACS (1975).97,1354 Ring 1 Atom Internal Cartesian coordinates X Y Z C1 0.0000(0.0000) 1.4755(0.0018) 0.1552(0.0014) C2 1.2456(0.0020) 0.7323(0.0025) -0.3070(0.0013) C3 1.2962(0.0017) -0.7103(0.0023) 0.1144(0.0014) C4 - 0.0176(0.0022) -1.4395(0.0016) 0.2301(0.0013) C5 - 1.2376(0.0014) -0.7332(0.0019) -0.3819(0.0012) C10 - 1.2867(0.0019) 0.6752(0.0023) 0.1892(0.0013) q2 = 0.5980(0.0018) q3 = -0.0916(0.0018) phi2 = 56.08 (1/5) Total puckering amplitude: QT = 0.6050(0.0017) Spherical polar angles: Theta2 = 98.71 (0.17) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C1 C2 C3 C4 C5 C10 DS(C1) =0.3354(0.0009) DS(C1 –C10) =0.0562(0.0008) D2(C1) =0.1362(0.0006) D2(C1 –C10) =0.3294(0.0007) DS(C2) =0.0281(0.0009) DS(C2 –C1) =0.3012(0.0008) D2(C2) =0.2369(0.0006) D2(C2 –C1) =0.1449(0.0008) DS(C3) =0.3635(0.0009) DS(C3 –C2) =0.2786(0.0007) D2(C3) =0.1098(0.0006) D2(C3 –C2) =0.1846(0.0008) Ring 2 Atom Internal Cartesian coordinates X Y Z C5 0.0000(0.0001) 1.3031(0.0013) -0.1867(0.0009) C6 1.2393(0.0018) 0.3662(0.0019) 0.0276(0.0011) C7 0.6974(0.0017) -1.0765(0.0018) 0.1421(0.0011) C8 - 0.7771(0.0013) -0.9894(0.0014) -0.2575(0.0010) C9 - 1.1597(0.0013) 0.3965(0.0014) 0.2745(0.0010) q2 = 0.4444(0.0016) phi2 = 131.64 (0.21) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C5 C6 C7 C8 C9 DS(C5) =0.2601(0.0009) D2(C5) =0.1692(0.0006) DS(C6) =0.3457(0.0008) D2(C6) =0.0244(0.0006) DS(C7) =0.2993(0.0008) D2(C7) =0.1292(0.0006) DS(C8) =0.1386(0.0008) D2(C8) =0.2329(0.0007) DS(C9) =0.0752(0.0008) D2(C9) =0.2465(0.0006) Ring 3 Atom Internal Cartesian coordinates X Y Z C8 0.0000(0.0000) 1.4786(0.0012) 0.2328(0.0011) C9 1.2441(0.0014) 0.7030(0.0017) -0.2155(0.0011) C11 1.2757(0.0017) -0.7580(0.0020) 0.2189(0.0012) C12 - 0.0230(0.0017) -1.4554(0.0015) -0.2395(0.0012) C13 - 1.2648(0.0014) -0.7105(0.0016) 0.2568(0.0011) C14 - 1.2320(0.0017) 0.7423(0.0016) -0.2534(0.0011) q2 = 0.0384(0.0015) q3 = 0.5784(0.0016) phi2 = -98.80 (2.42) Total puckering amplitude: QT = 0.5797(0.0016) Spherical polar angles: Theta2 = 3.79 (0.15) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C8 C9 C11 C12 C13 C14 DS(C8) =0.0265(0.0008) DS(C8 –C14) =0.3204(0.0006) D2(C8) =0.2536(0.0005) D2(C8 –C14) =0.0202(0.0006) DS(C9) =0.0104(0.0008) DS(C9 –C8) =0.3205(0.0006) D2(C9) =0.2531(0.0005) D2(C9 –C8) =0.0177(0.0006) DS(C11) =0.0163(0.0008) DS(C11 –C9) =0.3210(0.0006) D2(C11) =0.2536(0.0005) D2(C11 –C9) =0.0044(0.0006) Ring 4 Atom Internal Cartesian coordinates X Y Z C13 0.0000(0.0000) 1.2555(0.0014) -0.2972(0.0010) C14 1.1529(0.0016) 0.4024(0.0018) 0.2640(0.0010) C15 0.7903(0.0013) -1.0317(0.0019) -0.1300(0.0012) C16 - 0.7586(0.0017) -1.0422(0.0020) -0.0537(0.0013) C17 - 1.1847(0.0014) 0.4160(0.0020) 0.2168(0.0011) q2 = 0.4741(0.0015) phi2 = -172.32 (0.24) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C13 C14 C15 C16 C17 DS(C13) =0.0502(0.0009) D2(C13) =0.2699(0.0007) DS(C14) =0.1760(0.0009) D2(C14) =0.2380(0.0007) DS(C15) =0.3349(0.0009) D2(C15) =0.1187(0.0007) DS(C16) =0.3659(0.0009) D2(C16) =0.0486(0.0007) DS(C17) =0.2571(0.0009) D2(C17) =0.1961(0.0007) Possible hydrogen bonds Donor-H Donor···Acceptor H···Acceptor Donor-H······Acceptor C8 –H8 C8 ···O19 (0) H8 ···O19 (0) C8 –H8 ···O19 (0) 0.967(.019) 3.139(.002) 2.531(.018) 120.87(1.30) C11 –H11B C11 ···O19 (0) H11B ···O19 (0) C11 –H11B ···O19 (0) 1.014(.018) 3.115(.002) 2.492(.018) 119.20(1.30) C18 –H20C C18 ···O21 (0) H20C ···O21 (0) C18 –H20C ···O21 (0) 0.981(.025) 2.816(.002) 2.562(.023) 94.65(1.41) C4 –H4B C4 ···O19 (1) H4B ···O19 (1) C4 –H4B ···O19 (1) 0.948(.024) 3.388(.002) 2.767(.023) 123.79(1.76) C1 –H1A C1 ···O19 (1) H1A ···O19 (1) C1 –H1A ···O19 (1) 0.990(.022) 3.130(.002) 2.430(.022) 127.24(1.63) C6 –H6B C6 ···O20 (2) H6B ···O20 (2) C6 –H6B ···O20 (2) 1.015(.022) 3.632(.002) 2.714(.023) 150.66(1.69) C1 –H1B C1 ···O20 (2) H1B ···O20 (2) C1 –H1B ···O20 (2) 0.969(.023) 3.660(.002) 2.868(.023) 139.47(1.77) C7 –H7A C7 ···O20 (3) H7A ···O20 (3) C7 –H7A ···O20 (3) 0.995(.019) 3.542(.002) 2.822(.019) 129.79(1.40) C7 –H7A C7 ···O21 (4) H7A ···O21 (4) C7 –H7A ···O21 (4) 0.995(.019) 3.812(.002) 2.867(.019) 158.73(1.47) O21 –H21 O21 ···O20 (5) H21 ···O20 (5) O21 –H21 ···O20 (5) 0.819(.024) 2.863(.002) 2.047(.024) 173.94(2.34) Number of possible hydrogen bonds 10 Equivalent positions: (0) x,y,z (1) x - 1/2,-y + 1/2,-z + 1 (2) x + 1,+y,+z (3) x + 1/2,-y - 1/2,-z + 1 (4) -x,+y - 1/2,-z + 1/2 (5) -x - 1/2,-y,+z - 1/2 |
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 | ||
O19 | 0.1030 (3) | 0.19403 (14) | 0.47279 (6) | 0.0569 (4) | |
O20 | −0.5437 (2) | −0.03301 (17) | 0.56061 (6) | 0.0551 (4) | |
O21 | 0.1927 (3) | 0.12774 (15) | 0.17262 (5) | 0.0534 (4) | |
C1 | −0.0470 (3) | 0.11623 (19) | 0.56149 (7) | 0.0383 (4) | |
C2 | −0.2020 (3) | 0.0201 (2) | 0.58502 (7) | 0.0424 (4) | |
C3 | −0.3757 (3) | −0.00555 (16) | 0.54299 (7) | 0.0362 (3) | |
C4 | −0.3315 (2) | 0.00163 (19) | 0.47690 (7) | 0.0353 (3) | |
C5 | −0.1060 (2) | 0.00540 (14) | 0.45926 (6) | 0.0270 (3) | |
C6 | 0.0112 (3) | −0.12198 (17) | 0.47397 (7) | 0.0373 (4) | |
C7 | 0.1479 (3) | −0.15174 (16) | 0.41949 (7) | 0.0344 (3) | |
C8 | 0.1384 (2) | −0.03157 (14) | 0.38011 (6) | 0.0257 (3) | |
C9 | −0.0801 (2) | 0.01390 (15) | 0.39076 (6) | 0.0264 (3) | |
C10 | −0.0064 (3) | 0.11301 (16) | 0.49474 (7) | 0.0332 (3) | |
C11 | −0.1399 (3) | 0.13468 (17) | 0.35637 (7) | 0.0348 (3) | |
C12 | −0.0963 (3) | 0.11458 (18) | 0.28913 (7) | 0.0350 (3) | |
C13 | 0.1244 (2) | 0.07441 (14) | 0.27837 (6) | 0.0280 (3) | |
C14 | 0.1701 (2) | −0.04966 (15) | 0.31347 (6) | 0.0271 (3) | |
C15 | 0.3764 (3) | −0.09394 (19) | 0.28954 (7) | 0.0378 (4) | |
C16 | 0.3706 (3) | −0.0527 (2) | 0.22287 (7) | 0.0424 (4) | |
C17 | 0.1735 (3) | 0.02574 (17) | 0.21490 (7) | 0.0359 (3) | |
C18 | 0.2685 (3) | 0.18544 (18) | 0.29372 (8) | 0.0377 (4) | |
H1A | −0.099 (3) | 0.204 (2) | 0.5700 (9) | 0.049 (6)* | |
H1B | 0.085 (4) | 0.105 (2) | 0.5799 (10) | 0.057 (6)* | |
H2A | −0.249 (4) | 0.043 (2) | 0.6212 (10) | 0.053 (6)* | |
H2B | −0.141 (4) | −0.067 (2) | 0.5914 (10) | 0.058 (7)* | |
H4A | −0.410 (4) | −0.073 (2) | 0.4592 (10) | 0.054 (6)* | |
H4B | −0.391 (4) | 0.079 (2) | 0.4628 (10) | 0.059 (7)* | |
H6A | −0.084 (3) | −0.191 (2) | 0.4782 (10) | 0.054 (6)* | |
H6B | 0.102 (3) | −0.111 (2) | 0.5103 (10) | 0.053 (6)* | |
H7A | 0.091 (3) | −0.2261 (19) | 0.3971 (8) | 0.039 (5)* | |
H7B | 0.289 (4) | −0.173 (2) | 0.4326 (9) | 0.053 (6)* | |
H8 | 0.228 (3) | 0.0330 (18) | 0.3964 (7) | 0.031 (5)* | |
H9 | −0.167 (3) | −0.0544 (18) | 0.3737 (8) | 0.034 (5)* | |
H11A | −0.285 (3) | 0.155 (2) | 0.3603 (9) | 0.049 (6)* | |
H11B | −0.061 (3) | 0.2109 (17) | 0.3726 (8) | 0.036 (5)* | |
H12A | −0.186 (4) | 0.046 (2) | 0.2742 (9) | 0.052 (6)* | |
H12B | −0.129 (3) | 0.192 (2) | 0.2681 (8) | 0.039 (5)* | |
H14 | 0.068 (3) | −0.1142 (17) | 0.3010 (8) | 0.029 (4)* | |
H15A | 0.408 (3) | −0.1849 (19) | 0.2948 (9) | 0.041 (5)* | |
H15B | 0.491 (3) | −0.0506 (18) | 0.3115 (8) | 0.033 (5)* | |
H16A | 0.375 (4) | −0.126 (2) | 0.1970 (10) | 0.064 (7)* | |
H16B | 0.485 (4) | 0.002 (2) | 0.2131 (10) | 0.059 (7)* | |
H17 | 0.056 (3) | −0.0275 (17) | 0.2028 (8) | 0.030 (4)* | |
H20A | 0.409 (4) | 0.164 (3) | 0.2851 (12) | 0.068 (8)* | |
H20B | 0.252 (4) | 0.209 (2) | 0.3355 (10) | 0.059 (6)* | |
H20C | 0.246 (4) | 0.260 (3) | 0.2679 (10) | 0.064 (7)* | |
H21 | 0.154 (4) | 0.095 (2) | 0.1411 (11) | 0.059 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O19 | 0.0715 (10) | 0.0547 (8) | 0.0444 (7) | −0.0322 (8) | 0.0118 (7) | −0.0098 (6) |
O20 | 0.0423 (7) | 0.0836 (10) | 0.0395 (6) | −0.0083 (8) | 0.0123 (6) | 0.0056 (7) |
O21 | 0.0760 (10) | 0.0593 (8) | 0.0249 (5) | −0.0094 (9) | −0.0026 (6) | 0.0077 (6) |
C1 | 0.0395 (8) | 0.0482 (10) | 0.0274 (7) | −0.0020 (8) | −0.0029 (6) | −0.0064 (7) |
C2 | 0.0489 (10) | 0.0548 (11) | 0.0234 (7) | −0.0028 (9) | 0.0026 (7) | −0.0009 (7) |
C3 | 0.0384 (8) | 0.0395 (8) | 0.0306 (7) | −0.0005 (8) | 0.0065 (6) | 0.0019 (6) |
C4 | 0.0319 (7) | 0.0483 (9) | 0.0257 (6) | −0.0070 (8) | 0.0027 (6) | −0.0010 (7) |
C5 | 0.0284 (6) | 0.0308 (7) | 0.0217 (5) | −0.0020 (6) | 0.0014 (5) | −0.0011 (5) |
C6 | 0.0492 (9) | 0.0350 (8) | 0.0277 (6) | 0.0031 (8) | 0.0043 (7) | 0.0067 (6) |
C7 | 0.0399 (8) | 0.0322 (7) | 0.0311 (7) | 0.0057 (7) | 0.0023 (7) | 0.0048 (6) |
C8 | 0.0263 (6) | 0.0282 (7) | 0.0227 (6) | 0.0006 (6) | −0.0004 (5) | 0.0000 (5) |
C9 | 0.0262 (6) | 0.0312 (7) | 0.0218 (6) | −0.0001 (6) | 0.0005 (5) | 0.0007 (5) |
C10 | 0.0344 (7) | 0.0355 (7) | 0.0296 (6) | −0.0022 (7) | −0.0006 (6) | −0.0032 (6) |
C11 | 0.0355 (8) | 0.0393 (8) | 0.0296 (7) | 0.0099 (7) | 0.0038 (6) | 0.0067 (6) |
C12 | 0.0338 (8) | 0.0438 (8) | 0.0272 (7) | 0.0052 (7) | −0.0017 (6) | 0.0083 (7) |
C13 | 0.0294 (7) | 0.0330 (7) | 0.0216 (5) | −0.0031 (6) | −0.0019 (5) | 0.0010 (5) |
C14 | 0.0263 (6) | 0.0313 (7) | 0.0237 (6) | −0.0010 (6) | 0.0007 (5) | −0.0016 (5) |
C15 | 0.0350 (8) | 0.0470 (9) | 0.0313 (7) | 0.0060 (8) | 0.0052 (7) | −0.0016 (7) |
C16 | 0.0446 (10) | 0.0531 (10) | 0.0294 (7) | 0.0017 (9) | 0.0098 (7) | −0.0045 (7) |
C17 | 0.0412 (8) | 0.0439 (9) | 0.0226 (6) | −0.0076 (8) | −0.0012 (6) | −0.0024 (6) |
C18 | 0.0443 (10) | 0.0380 (8) | 0.0308 (7) | −0.0115 (7) | −0.0004 (7) | −0.0006 (7) |
O19—C10 | 1.212 (2) | C8—C9 | 1.533 (2) |
O20—C3 | 1.208 (2) | C8—H8 | 0.967 (19) |
O21—C17 | 1.426 (2) | C9—C11 | 1.525 (2) |
O21—H21 | 0.82 (2) | C9—H9 | 0.990 (19) |
C1—C10 | 1.516 (2) | C11—C12 | 1.544 (2) |
C1—C2 | 1.522 (3) | C11—H11A | 0.98 (2) |
C1—H1A | 0.99 (2) | C11—H11B | 1.014 (19) |
C1—H1B | 0.97 (2) | C12—C13 | 1.531 (2) |
C2—C3 | 1.504 (3) | C12—H12A | 0.99 (2) |
C2—H2A | 0.90 (2) | C12—H12B | 0.95 (2) |
C2—H2B | 1.00 (2) | C13—C18 | 1.534 (2) |
C3—C4 | 1.507 (2) | C13—C14 | 1.540 (2) |
C4—C5 | 1.537 (2) | C13—C17 | 1.540 (2) |
C4—H4A | 1.01 (2) | C14—C15 | 1.531 (2) |
C4—H4B | 0.95 (2) | C14—H14 | 0.991 (18) |
C5—C10 | 1.521 (2) | C15—C16 | 1.551 (2) |
C5—C9 | 1.5424 (19) | C15—H15A | 0.98 (2) |
C5—C6 | 1.568 (2) | C15—H15B | 1.006 (19) |
C6—C7 | 1.545 (2) | C16—C17 | 1.543 (3) |
C6—H6A | 0.96 (2) | C16—H16A | 0.96 (2) |
C6—H6B | 1.01 (2) | C16—H16B | 0.97 (2) |
C7—C8 | 1.530 (2) | C17—H17 | 0.991 (19) |
C7—H7A | 0.995 (19) | C18—H20A | 0.97 (3) |
C7—H7B | 1.00 (2) | C18—H20B | 0.97 (2) |
C8—C14 | 1.5154 (18) | C18—H20C | 0.98 (3) |
C17—O21—H21 | 103.7 (17) | O19—C10—C1 | 119.18 (15) |
C10—C1—C2 | 116.33 (14) | O19—C10—C5 | 123.86 (14) |
C10—C1—H1A | 105.6 (12) | C1—C10—C5 | 116.96 (14) |
C2—C1—H1A | 107.9 (13) | C9—C11—C12 | 109.32 (13) |
C10—C1—H1B | 104.8 (13) | C9—C11—H11A | 112.3 (13) |
C2—C1—H1B | 112.3 (14) | C12—C11—H11A | 107.2 (12) |
H1A—C1—H1B | 110 (2) | C9—C11—H11B | 109.4 (10) |
C3—C2—C1 | 114.27 (14) | C12—C11—H11B | 111.0 (10) |
C3—C2—H2A | 110.2 (15) | H11A—C11—H11B | 107.6 (17) |
C1—C2—H2A | 111.6 (15) | C13—C12—C11 | 111.48 (13) |
C3—C2—H2B | 103.5 (14) | C13—C12—H12A | 108.5 (13) |
C1—C2—H2B | 112.0 (14) | C11—C12—H12A | 108.4 (12) |
H2A—C2—H2B | 104.5 (19) | C13—C12—H12B | 111.5 (12) |
O20—C3—C2 | 122.34 (14) | C11—C12—H12B | 108.8 (12) |
O20—C3—C4 | 120.51 (15) | H12A—C12—H12B | 108.0 (17) |
C2—C3—C4 | 117.15 (14) | C12—C13—C18 | 110.28 (14) |
C3—C4—C5 | 116.05 (13) | C12—C13—C14 | 109.54 (13) |
C3—C4—H4A | 104.3 (13) | C18—C13—C14 | 113.36 (13) |
C5—C4—H4A | 114.5 (14) | C12—C13—C17 | 115.70 (13) |
C3—C4—H4B | 106.8 (14) | C18—C13—C17 | 108.88 (13) |
C5—C4—H4B | 107.0 (16) | C14—C13—C17 | 98.75 (12) |
H4A—C4—H4B | 107.8 (18) | C8—C14—C15 | 120.19 (13) |
C10—C5—C4 | 107.56 (13) | C8—C14—C13 | 111.67 (12) |
C10—C5—C9 | 115.31 (12) | C15—C14—C13 | 104.35 (12) |
C4—C5—C9 | 111.26 (12) | C8—C14—H14 | 105.5 (10) |
C10—C5—C6 | 107.50 (12) | C15—C14—H14 | 107.5 (10) |
C4—C5—C6 | 113.58 (13) | C13—C14—H14 | 107.0 (10) |
C9—C5—C6 | 101.66 (11) | C14—C15—C16 | 103.31 (14) |
C7—C6—C5 | 106.90 (12) | C14—C15—H15A | 116.1 (12) |
C7—C6—H6A | 108.0 (13) | C16—C15—H15A | 112.9 (12) |
C5—C6—H6A | 109.5 (13) | C14—C15—H15B | 111.1 (10) |
C7—C6—H6B | 107.9 (12) | C16—C15—H15B | 111.3 (10) |
C5—C6—H6B | 111.4 (12) | H15A—C15—H15B | 102.4 (16) |
H6A—C6—H6B | 112.9 (17) | C17—C16—C15 | 106.14 (13) |
C8—C7—C6 | 105.39 (13) | C17—C16—H16A | 112.1 (15) |
C8—C7—H7A | 109.2 (11) | C15—C16—H16A | 111.1 (14) |
C6—C7—H7A | 109.4 (11) | C17—C16—H16B | 108.4 (13) |
C8—C7—H7B | 112.9 (13) | C15—C16—H16B | 111.2 (14) |
C6—C7—H7B | 110.8 (12) | H16A—C16—H16B | 107.9 (19) |
H7A—C7—H7B | 109.0 (17) | O21—C17—C16 | 113.29 (15) |
C14—C8—C7 | 117.26 (12) | O21—C17—C13 | 112.57 (14) |
C14—C8—C9 | 108.68 (11) | C16—C17—C13 | 104.13 (12) |
C7—C8—C9 | 101.61 (12) | O21—C17—H17 | 107.7 (10) |
C14—C8—H8 | 111.8 (10) | C16—C17—H17 | 113.3 (11) |
C7—C8—H8 | 109.0 (10) | C13—C17—H17 | 105.7 (10) |
C9—C8—H8 | 107.6 (11) | C13—C18—H20A | 111.7 (16) |
C11—C9—C8 | 114.72 (12) | C13—C18—H20B | 109.4 (14) |
C11—C9—C5 | 121.26 (13) | H20A—C18—H20B | 111 (2) |
C8—C9—C5 | 103.89 (11) | C13—C18—H20C | 111.9 (14) |
C11—C9—H9 | 104.3 (11) | H20A—C18—H20C | 102 (2) |
C8—C9—H9 | 105.3 (11) | H20B—C18—H20C | 110.5 (19) |
C5—C9—H9 | 106.1 (10) | ||
C10—C1—C2—C3 | −35.3 (2) | C9—C5—C10—C1 | 173.64 (14) |
C1—C2—C3—O20 | −149.19 (19) | C6—C5—C10—C1 | −73.80 (17) |
C1—C2—C3—C4 | 32.0 (2) | C8—C9—C11—C12 | 53.84 (18) |
O20—C3—C4—C5 | −166.03 (17) | C5—C9—C11—C12 | 179.89 (13) |
C2—C3—C4—C5 | 12.8 (2) | C9—C11—C12—C13 | −54.33 (19) |
C3—C4—C5—C10 | −52.31 (19) | C11—C12—C13—C18 | −67.68 (18) |
C3—C4—C5—C9 | −179.49 (14) | C11—C12—C13—C14 | 57.74 (17) |
C3—C4—C5—C6 | 66.53 (19) | C11—C12—C13—C17 | 168.22 (14) |
C10—C5—C6—C7 | −103.93 (15) | C7—C8—C14—C15 | −66.1 (2) |
C4—C5—C6—C7 | 137.20 (14) | C9—C8—C14—C15 | 179.53 (14) |
C9—C5—C6—C7 | 17.59 (16) | C7—C8—C14—C13 | 171.27 (13) |
C5—C6—C7—C8 | 10.05 (18) | C9—C8—C14—C13 | 56.86 (15) |
C6—C7—C8—C14 | −152.13 (14) | C12—C13—C14—C8 | −59.65 (15) |
C6—C7—C8—C9 | −33.86 (16) | C18—C13—C14—C8 | 63.97 (17) |
C14—C8—C9—C11 | −55.18 (16) | C17—C13—C14—C8 | 179.00 (13) |
C7—C8—C9—C11 | −179.44 (13) | C12—C13—C14—C15 | 169.03 (13) |
C14—C8—C9—C5 | 170.21 (12) | C18—C13—C14—C15 | −67.35 (16) |
C7—C8—C9—C5 | 45.94 (14) | C17—C13—C14—C15 | 47.68 (14) |
C10—C5—C9—C11 | −53.97 (19) | C8—C14—C15—C16 | −159.99 (14) |
C4—C5—C9—C11 | 68.87 (19) | C13—C14—C15—C16 | −33.84 (17) |
C6—C5—C9—C11 | −169.90 (14) | C14—C15—C16—C17 | 6.3 (2) |
C10—C5—C9—C8 | 76.88 (16) | C15—C16—C17—O21 | 145.84 (15) |
C4—C5—C9—C8 | −160.28 (13) | C15—C16—C17—C13 | 23.21 (19) |
C6—C5—C9—C8 | −39.05 (14) | C12—C13—C17—O21 | 77.40 (19) |
C2—C1—C10—O19 | 174.09 (18) | C18—C13—C17—O21 | −47.42 (19) |
C2—C1—C10—C5 | −6.5 (2) | C14—C13—C17—O21 | −165.89 (14) |
C4—C5—C10—O19 | −131.77 (18) | C12—C13—C17—C16 | −159.50 (14) |
C9—C5—C10—O19 | −7.0 (2) | C18—C13—C17—C16 | 75.68 (17) |
C6—C5—C10—O19 | 105.57 (19) | C14—C13—C17—C16 | −42.78 (15) |
C4—C5—C10—C1 | 48.86 (19) |
C18H26O3 | Dx = 1.234 Mg m−3 |
Mr = 290.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 60 reflections |
a = 6.6278 (5) Å | θ = 3.7–12.5° |
b = 11.1491 (9) Å | µ = 0.08 mm−1 |
c = 21.1609 (19) Å | T = 293 K |
V = 1563.7 (2) Å3 | Squared prism, colourless |
Z = 4 | 0.34 × 0.24 × 0.22 mm |
F(000) = 632 |
Bruker P4 diffractometer | Rint = 0.026 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.9° |
Graphite monochromator | h = 0→8 |
2θ/ω scans | k = 0→14 |
4127 measured reflections | l = 0→27 |
2094 independent reflections | 3 standard reflections every 197 reflections |
1400 reflections with I > 2σ(I) | intensity decay: 0.0% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max = 0.002 |
S = 0.96 | Δρmax = 0.12 e Å−3 |
2094 reflections | Δρmin = −0.13 e Å−3 |
295 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.011 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: based on the reagents configuration |
Secondary atom site location: difference Fourier map |
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. Ring puckering coordinates following Cremer D. & Pople J·A., JACS (1975).97,1354 Ring 1 Atom Internal Cartesian coordinates X Y Z C1 0.0000(0.0000) 1.3958(0.0025) 0.3440(0.0022) C2 1.2386(0.0035) 0.7610(0.0032) -0.2791(0.0022) C3 1.2864(0.0025) -0.7216(0.0035) -0.0767(0.0020) C4 - 0.0002(0.0036) -1.3718(0.0021) 0.3677(0.0018) C5 - 1.2426(0.0026) -0.7832(0.0031) -0.3029(0.0019) C10 - 1.2821(0.0034) 0.7199(0.0035) -0.0530(0.0020) q2 = 0.6565(0.0029) q3 = -0.0291(0.0029) phi2 = 20.15 (0.24) Total puckering amplitude: QT = 0.6571(0.0029) Spherical polar angles: Theta2 = 92.54 (0.26) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C1 C2 C3 C4 C5 C10 DS(C1) =0.1513(0.0014) DS(C1 –C10) =0.2398(0.0012) D2(C1) =0.2445(0.0009) D2(C1 –C10) =0.2809(0.0012) DS(C2) =0.2931(0.0014) DS(C2 –C1) =0.3632(0.0012) D2(C2) =0.2007(0.0009) D2(C2 –C1) =0.0672(0.0011) DS(C3) =0.4443(0.0015) DS(C3 –C2) =0.1246(0.0011) D2(C3) =0.0508(0.0009) D2(C3 –C2) =0.3477(0.0012) Ring 2 Atom Internal Cartesian coordinates X Y Z C5 0.0000(0.0000) 1.2787(0.0020) 0.2566(0.0016) C6 1.1788(0.0032) 0.4102(0.0031) -0.2392(0.0019) C7 0.7876(0.0027) -1.0203(0.0033) 0.1304(0.0019) C8 - 0.7603(0.0027) -1.0741(0.0028) 0.0283(0.0018) C9 - 1.2061(0.0025) 0.4055(0.0031) -0.1761(0.0016) q2 = 0.4146(0.0027) phi2 = 11.81 (0.39) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C5 C6 C7 C8 C9 DS(C5) =0.0666(0.0014) D2(C5) =0.2305(0.0011) DS(C6) =0.1311(0.0013) D2(C6) =0.2139(0.0011) DS(C7) =0.2788(0.0013) D2(C7) =0.1176(0.0011) DS(C8) =0.3199(0.0014) D2(C8) =0.0249(0.0011) DS(C9) =0.2389(0.0015) D2(C9) =0.1572(0.0010) Ring 3 Atom Internal Cartesian coordinates X Y Z C8 0.0000(0.0000) 1.5249(0.0023) 0.1002(0.0018) C9 1.3231(0.0028) 0.7132(0.0033) -0.0420(0.0019) C11 1.2467(0.0026) -0.8063(0.0032) 0.1236(0.0021) C12 - 0.0779(0.0028) -1.4573(0.0026) -0.2634(0.0020) C13 - 1.2559(0.0020) -0.6988(0.0030) 0.3215(0.0016) C14 - 1.2360(0.0028) 0.7242(0.0031) -0.2399(0.0017) q2 = 0.2432(0.0025) q3 = 0.4452(0.0026) phi2 = -125.53 (2/3) Total puckering amplitude: QT = 0.5073(0.0024) Spherical polar angles: Theta2 = 28.64 (0.30) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C8 C9 C11 C12 C13 C14 DS(C8) =0.1363(0.0013) DS(C8 –C14) =0.2461(0.0011) D2(C8) =0.2024(0.0009) D2(C8 –C14) =0.1355(0.0010) DS(C9) =0.0151(0.0013) DS(C9 –C8) =0.2751(0.0011) D2(C9) =0.2168(0.0009) D2(C9 –C8) =0.0572(0.0011) DS(C11) =0.1512(0.0013) DS(C11 –C9) =0.2699(0.0010) D2(C11) =0.1981(0.0008) D2(C11 –C9) =0.0783(0.0011) Ring 4 Atom Internal Cartesian coordinates X Y Z C13 0.0000(0.0000) 1.2491(0.0022) -0.2913(0.0016) C14 1.1603(0.0025) 0.4119(0.0030) 0.2501(0.0016) C15 0.7789(0.0028) -1.0272(0.0032) -0.1134(0.0018) C16 - 0.7591(0.0027) -1.0420(0.0030) -0.0667(0.0019) C17 - 1.1801(0.0026) 0.4082(0.0031) 0.2212(0.0018) q2 = 0.4622(0.0026) phi2 = -175.18 (0.37) Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141 C13 C14 C15 C16 C17 DS(C13) =0.0308(0.0015) D2(C13) =0.2649(0.0011) DS(C14) =0.1879(0.0015) D2(C14) =0.2264(0.0011) DS(C15) =0.3347(0.0014) D2(C15) =0.1036(0.0011) DS(C16) =0.3538(0.0014) D2(C16) =0.0605(0.0011) DS(C17) =0.2377(0.0014) D2(C17) =0.2005(0.0011) Possible hydrogen bonds Donor-H Donor···Acceptor H···Acceptor Donor-H······Acceptor C6 –H6B C6 ···O19 (0) H6B ···O19 (0) C6 –H6B ···O19 (0) 0.947(.036) 3.149(.004) 2.793(.035) 103.33(2.33) C9 –H9 C9 ···O19 (0) H9 ···O19 (0) C9 –H9 ···O19 (0) 0.910(.029) 2.874(.003) 2.423(.027) 110.66(1.98) C18 –H18B C18 ···O21 (0) H18B ···O21 (0) C18 –H18B ···O21 (0) 0.951(.039) 2.925(.004) 2.661(.038) 96.45(2.53) C11 –H11B C11 ···O19 (1) H11B ···O19 (1) C11 –H11B ···O19 (1) 0.932(.028) 3.469(.004) 2.552(.028) 168.23(2.29) C1 –H1B C1 ···O19 (1) H1B ···O19 (1) C1 –H1B ···O19 (1) 1.027(.029) 3.567(.004) 2.695(.028) 142.82(2.11) C2 –H2A C2 ···O21 (2) H2A ···O21 (2) C2 –H2A ···O21 (2) 0.931(.039) 3.459(.004) 2.605(.037) 152.73(3.06) C2 –H2B C2 ···O20 (3) H2B ···O20 (3) C2 –H2B ···O20 (3) 0.944(.034) 3.685(.004) 2.796(.034) 157.36(2.69) C6 –H6A C6 ···O20 (3) H6A ···O20 (3) C6 –H6A ···O20 (3) 0.983(.034) 3.585(.004) 2.645(.033) 160.09(2.65) C7 –H7A C7 ···O21 (4) H7A ···O21 (4) C7 –H7A ···O21 (4) 1.077(.027) 3.719(.004) 2.731(.027) 152.34(1.95) C4 –H4B C4 ···O21 (4) H4B ···O21 (4) C4 –H4B ···O21 (4) 0.978(.028) 3.633(.004) 2.968(.027) 126.26(1.98) C7 –H7B C7 ···O20 (5) H7B ···O20 (5) C7 –H7B ···O20 (5) 0.970(.032) 3.672(.004) 2.914(.030) 135.79(2.31) C16 –H16B C16 ···O20 (6) H16B ···O20 (6) C16 –H16B ···O20 (6) 1.014(.027) 3.743(.004) 2.959(.027) 134.85(1.91) O21 –H21 O21 ···O20 (6) H21 ···O20 (6) O21 –H21 ···O20 (6) 0.915(.042) 2.862(.003) 2.033(.038) 150.04(3.40) Number of possible hydrogen bonds 13 Equivalent positions: (0) x,y,z (1) x - 1/2,-y + 1/2,-z (2) -x - 1/2,-y + 1,+z - 1/2 (3) x + 1/2,-y + 1/2 + 1,-z (4) -x,+y + 1/2,-z + 1/2 (5) x + 1,+y,+z (6) -x,+y - 1/2,-z + 1/2 |
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 | ||
O19 | 0.1626 (4) | 0.3088 (2) | −0.02593 (9) | 0.0874 (8) | |
O20 | −0.1972 (3) | 0.71231 (16) | 0.05072 (8) | 0.0640 (6) | |
O21 | −0.0468 (4) | 0.3123 (2) | 0.35090 (9) | 0.0753 (7) | |
C1 | −0.1000 (5) | 0.4460 (2) | −0.04383 (13) | 0.0573 (7) | |
C2 | −0.1275 (6) | 0.5806 (3) | −0.03453 (13) | 0.0554 (7) | |
C3 | −0.1371 (4) | 0.6152 (2) | 0.03377 (11) | 0.0453 (6) | |
C4 | −0.0671 (4) | 0.5215 (2) | 0.08033 (11) | 0.0450 (7) | |
C5 | 0.1175 (4) | 0.4512 (2) | 0.05785 (10) | 0.0448 (6) | |
C6 | 0.3049 (5) | 0.5331 (3) | 0.05274 (14) | 0.0579 (7) | |
C7 | 0.3777 (5) | 0.5483 (3) | 0.12081 (15) | 0.0589 (7) | |
C8 | 0.3248 (4) | 0.4291 (2) | 0.15490 (12) | 0.0486 (6) | |
C9 | 0.1918 (4) | 0.3580 (2) | 0.10705 (11) | 0.0479 (6) | |
C10 | 0.0715 (5) | 0.3945 (2) | −0.00610 (12) | 0.0539 (7) | |
C11 | 0.0315 (5) | 0.2734 (2) | 0.13390 (13) | 0.0556 (8) | |
C12 | −0.0559 (4) | 0.3078 (3) | 0.19812 (12) | 0.0507 (7) | |
C13 | 0.1097 (4) | 0.3416 (2) | 0.24440 (10) | 0.0423 (6) | |
C14 | 0.2227 (4) | 0.4501 (2) | 0.21781 (11) | 0.0417 (5) | |
C15 | 0.3491 (5) | 0.4948 (3) | 0.27369 (14) | 0.0601 (7) | |
C16 | 0.2222 (5) | 0.4638 (3) | 0.33235 (13) | 0.0652 (8) | |
C17 | 0.0375 (5) | 0.3951 (3) | 0.30742 (12) | 0.0545 (7) | |
C18 | 0.2494 (6) | 0.2336 (3) | 0.25718 (15) | 0.0602 (8) | |
H1A | −0.087 (4) | 0.421 (2) | −0.0866 (13) | 0.057 (7)* | |
H1B | −0.221 (5) | 0.402 (3) | −0.0244 (13) | 0.064 (8)* | |
H2A | −0.241 (6) | 0.615 (3) | −0.0527 (16) | 0.100 (13)* | |
H2B | −0.012 (5) | 0.621 (3) | −0.0499 (14) | 0.072 (10)* | |
H4A | −0.175 (4) | 0.465 (2) | 0.0845 (11) | 0.049 (7)* | |
H4B | −0.036 (4) | 0.556 (2) | 0.1217 (13) | 0.057 (7)* | |
H6A | 0.275 (5) | 0.609 (3) | 0.0310 (15) | 0.088 (11)* | |
H6B | 0.399 (6) | 0.489 (3) | 0.0283 (17) | 0.104 (13)* | |
H7A | 0.298 (4) | 0.618 (2) | 0.1455 (12) | 0.064 (8)* | |
H7B | 0.521 (5) | 0.565 (3) | 0.1224 (13) | 0.063 (8)* | |
H8 | 0.452 (4) | 0.380 (2) | 0.1631 (10) | 0.047 (7)* | |
H9 | 0.270 (5) | 0.308 (3) | 0.0836 (12) | 0.069 (9)* | |
H11A | 0.100 (5) | 0.189 (3) | 0.1376 (12) | 0.075 (9)* | |
H11B | −0.075 (5) | 0.263 (2) | 0.1058 (12) | 0.054 (8)* | |
H12A | −0.131 (5) | 0.240 (3) | 0.2148 (12) | 0.060 (8)* | |
H12B | −0.149 (4) | 0.378 (2) | 0.1954 (11) | 0.048 (7)* | |
H14 | 0.119 (3) | 0.5106 (18) | 0.2115 (9) | 0.031 (5)* | |
H15A | 0.403 (5) | 0.580 (3) | 0.2712 (14) | 0.082 (9)* | |
H15B | 0.475 (4) | 0.446 (2) | 0.2730 (11) | 0.057 (7)* | |
H16A | 0.178 (5) | 0.536 (3) | 0.3564 (14) | 0.085 (10)* | |
H16B | 0.302 (4) | 0.407 (2) | 0.3599 (12) | 0.068 (8)* | |
H17 | −0.069 (4) | 0.451 (2) | 0.2980 (10) | 0.039 (6)* | |
H18A | 0.355 (5) | 0.252 (2) | 0.2880 (13) | 0.066 (9)* | |
H18B | 0.167 (6) | 0.172 (3) | 0.2744 (17) | 0.109 (13)* | |
H18C | 0.311 (5) | 0.207 (3) | 0.2181 (13) | 0.071 (9)* | |
H21 | 0.057 (7) | 0.272 (3) | 0.3698 (16) | 0.113 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O19 | 0.121 (2) | 0.0855 (15) | 0.0552 (11) | 0.0414 (16) | 0.0129 (13) | −0.0148 (11) |
O20 | 0.0903 (15) | 0.0489 (10) | 0.0529 (10) | 0.0220 (11) | −0.0075 (11) | −0.0006 (9) |
O21 | 0.0834 (16) | 0.0901 (16) | 0.0523 (12) | 0.0005 (14) | 0.0113 (12) | 0.0199 (11) |
C1 | 0.079 (2) | 0.0490 (15) | 0.0435 (15) | −0.0022 (17) | 0.0000 (15) | −0.0056 (12) |
C2 | 0.073 (2) | 0.0505 (15) | 0.0427 (14) | 0.0045 (17) | −0.0024 (15) | −0.0003 (12) |
C3 | 0.0518 (15) | 0.0415 (13) | 0.0426 (12) | 0.0013 (13) | 0.0007 (12) | 0.0028 (11) |
C4 | 0.0525 (17) | 0.0474 (15) | 0.0350 (13) | 0.0098 (14) | 0.0049 (12) | 0.0032 (11) |
C5 | 0.0523 (14) | 0.0445 (13) | 0.0376 (11) | 0.0100 (14) | 0.0092 (11) | 0.0031 (11) |
C6 | 0.0549 (17) | 0.0599 (18) | 0.0589 (17) | 0.0040 (16) | 0.0145 (15) | 0.0138 (15) |
C7 | 0.0437 (15) | 0.0634 (18) | 0.0696 (18) | −0.0097 (16) | 0.0063 (14) | 0.0114 (16) |
C8 | 0.0370 (13) | 0.0518 (15) | 0.0569 (14) | 0.0077 (12) | 0.0036 (12) | 0.0113 (12) |
C9 | 0.0566 (16) | 0.0402 (13) | 0.0468 (13) | 0.0115 (13) | 0.0109 (13) | 0.0000 (11) |
C10 | 0.0702 (18) | 0.0484 (14) | 0.0431 (14) | 0.0047 (16) | 0.0134 (14) | 0.0019 (12) |
C11 | 0.076 (2) | 0.0397 (15) | 0.0513 (15) | −0.0057 (15) | −0.0082 (16) | 0.0014 (12) |
C12 | 0.0503 (17) | 0.0505 (15) | 0.0512 (15) | −0.0128 (15) | −0.0015 (13) | 0.0103 (13) |
C13 | 0.0451 (14) | 0.0399 (12) | 0.0419 (12) | 0.0035 (12) | 0.0003 (11) | 0.0045 (10) |
C14 | 0.0366 (12) | 0.0362 (11) | 0.0524 (13) | 0.0036 (11) | −0.0044 (11) | 0.0081 (11) |
C15 | 0.0562 (18) | 0.0548 (17) | 0.0693 (18) | −0.0057 (15) | −0.0172 (16) | 0.0013 (14) |
C16 | 0.085 (2) | 0.0580 (18) | 0.0521 (15) | 0.0044 (18) | −0.0140 (16) | −0.0022 (15) |
C17 | 0.0605 (17) | 0.0577 (16) | 0.0454 (14) | 0.0103 (16) | 0.0046 (13) | 0.0076 (13) |
C18 | 0.074 (2) | 0.0475 (16) | 0.0595 (17) | 0.0137 (16) | −0.0058 (18) | 0.0069 (14) |
O19—C10 | 1.206 (3) | C8—C9 | 1.559 (4) |
O20—C3 | 1.208 (3) | C8—H8 | 1.02 (2) |
O21—C17 | 1.418 (3) | C9—C11 | 1.530 (4) |
O21—H21 | 0.91 (4) | C9—H9 | 0.91 (3) |
C1—C10 | 1.503 (4) | C11—C12 | 1.526 (4) |
C1—C2 | 1.525 (4) | C11—H11A | 1.05 (3) |
C1—H1A | 0.95 (3) | C11—H11B | 0.93 (3) |
C1—H1B | 1.03 (3) | C12—C13 | 1.518 (3) |
C2—C3 | 1.497 (4) | C12—H12A | 0.97 (3) |
C2—H2A | 0.93 (4) | C12—H12B | 1.00 (3) |
C2—H2B | 0.94 (3) | C13—C14 | 1.530 (3) |
C3—C4 | 1.509 (3) | C13—C17 | 1.537 (3) |
C4—C5 | 1.530 (3) | C13—C18 | 1.543 (4) |
C4—H4A | 0.95 (3) | C14—C15 | 1.533 (4) |
C4—H4B | 0.98 (3) | C14—H14 | 0.97 (2) |
C5—C10 | 1.524 (3) | C15—C16 | 1.539 (5) |
C5—C6 | 1.546 (4) | C15—H15A | 1.01 (3) |
C5—C9 | 1.551 (3) | C15—H15B | 1.00 (3) |
C6—C7 | 1.528 (4) | C16—C17 | 1.537 (4) |
C6—H6A | 0.98 (3) | C16—H16A | 0.99 (3) |
C6—H6B | 0.95 (4) | C16—H16B | 1.01 (3) |
C7—C8 | 1.552 (4) | C17—H17 | 0.97 (2) |
C7—H7A | 1.08 (3) | C18—H18A | 0.98 (3) |
C7—H7B | 0.97 (3) | C18—H18B | 0.95 (4) |
C8—C14 | 1.511 (3) | C18—H18C | 0.97 (3) |
C17—O21—H21 | 108 (2) | O19—C10—C1 | 119.8 (2) |
C10—C1—C2 | 113.4 (3) | O19—C10—C5 | 122.5 (3) |
C10—C1—H1A | 108.9 (16) | C1—C10—C5 | 117.7 (2) |
C2—C1—H1A | 114.9 (15) | C12—C11—C9 | 116.1 (2) |
C10—C1—H1B | 101.4 (15) | C12—C11—H11A | 108.9 (15) |
C2—C1—H1B | 108.8 (16) | C9—C11—H11A | 106.3 (17) |
H1A—C1—H1B | 108 (2) | C12—C11—H11B | 108.2 (16) |
C3—C2—C1 | 112.5 (2) | C9—C11—H11B | 111.6 (16) |
C3—C2—H2A | 105 (2) | H11A—C11—H11B | 105 (2) |
C1—C2—H2A | 117 (2) | C13—C12—C11 | 111.3 (2) |
C3—C2—H2B | 104.2 (19) | C13—C12—H12A | 109.2 (16) |
C1—C2—H2B | 109 (2) | C11—C12—H12A | 108.9 (16) |
H2A—C2—H2B | 108 (3) | C13—C12—H12B | 107.0 (14) |
O20—C3—C2 | 122.1 (2) | C11—C12—H12B | 112.4 (14) |
O20—C3—C4 | 121.8 (2) | H12A—C12—H12B | 108 (2) |
C2—C3—C4 | 116.1 (2) | C12—C13—C14 | 108.25 (19) |
C3—C4—C5 | 113.4 (2) | C12—C13—C17 | 115.5 (2) |
C3—C4—H4A | 106.6 (14) | C14—C13—C17 | 99.49 (19) |
C5—C4—H4A | 106.8 (15) | C12—C13—C18 | 110.7 (2) |
C3—C4—H4B | 112.3 (16) | C14—C13—C18 | 112.8 (2) |
C5—C4—H4B | 108.0 (16) | C17—C13—C18 | 109.7 (2) |
H4A—C4—H4B | 110 (2) | C8—C14—C13 | 114.9 (2) |
C10—C5—C4 | 109.2 (2) | C8—C14—C15 | 119.0 (2) |
C10—C5—C6 | 110.1 (2) | C13—C14—C15 | 104.0 (2) |
C4—C5—C6 | 111.2 (2) | C8—C14—H14 | 107.6 (12) |
C10—C5—C9 | 112.5 (2) | C13—C14—H14 | 104.8 (12) |
C4—C5—C9 | 112.88 (19) | C15—C14—H14 | 105.4 (12) |
C6—C5—C9 | 100.8 (2) | C14—C15—C16 | 104.5 (2) |
C7—C6—C5 | 104.7 (2) | C14—C15—H15A | 117.1 (17) |
C7—C6—H6A | 114.1 (19) | C16—C15—H15A | 116.3 (18) |
C5—C6—H6A | 112 (2) | C14—C15—H15B | 105.5 (15) |
C7—C6—H6B | 111 (2) | C16—C15—H15B | 110.2 (15) |
C5—C6—H6B | 105 (2) | H15A—C15—H15B | 103 (2) |
H6A—C6—H6B | 109 (3) | C17—C16—C15 | 105.7 (2) |
C6—C7—C8 | 105.8 (2) | C17—C16—H16A | 110 (2) |
C6—C7—H7A | 112.6 (14) | C15—C16—H16A | 113.1 (17) |
C8—C7—H7A | 106.6 (13) | C17—C16—H16B | 107.5 (15) |
C6—C7—H7B | 111.3 (17) | C15—C16—H16B | 108.7 (15) |
C8—C7—H7B | 111.5 (17) | H16A—C16—H16B | 111 (2) |
H7A—C7—H7B | 109 (2) | O21—C17—C16 | 114.6 (2) |
C14—C8—C7 | 112.2 (2) | O21—C17—C13 | 115.7 (2) |
C14—C8—C9 | 113.4 (2) | C16—C17—C13 | 104.1 (2) |
C7—C8—C9 | 105.1 (2) | O21—C17—H17 | 105.6 (14) |
C14—C8—H8 | 107.7 (13) | C16—C17—H17 | 109.2 (13) |
C7—C8—H8 | 110.8 (13) | C13—C17—H17 | 107.4 (13) |
C9—C8—H8 | 107.6 (13) | C13—C18—H18A | 112.7 (17) |
C11—C9—C5 | 116.2 (2) | C13—C18—H18B | 107 (2) |
C11—C9—C8 | 117.7 (2) | H18A—C18—H18B | 108 (3) |
C5—C9—C8 | 105.99 (19) | C13—C18—H18C | 110.3 (17) |
C11—C9—H9 | 102.6 (19) | H18A—C18—H18C | 109 (2) |
C5—C9—H9 | 103.0 (17) | H18B—C18—H18C | 110 (3) |
C8—C9—H9 | 110.2 (19) | ||
C10—C1—C2—C3 | −50.9 (4) | C6—C5—C10—C1 | −102.9 (3) |
C1—C2—C3—O20 | −165.2 (3) | C9—C5—C10—C1 | 145.6 (2) |
C1—C2—C3—C4 | 14.9 (4) | C5—C9—C11—C12 | −98.2 (3) |
O20—C3—C4—C5 | −141.0 (3) | C8—C9—C11—C12 | 29.0 (4) |
C2—C3—C4—C5 | 38.9 (4) | C9—C11—C12—C13 | −46.6 (3) |
C3—C4—C5—C10 | −55.9 (3) | C11—C12—C13—C14 | 61.0 (3) |
C3—C4—C5—C6 | 65.7 (3) | C11—C12—C13—C17 | 171.5 (2) |
C3—C4—C5—C9 | 178.2 (2) | C11—C12—C13—C18 | −63.0 (3) |
C10—C5—C6—C7 | −161.0 (2) | C7—C8—C14—C13 | 162.1 (2) |
C4—C5—C6—C7 | 77.9 (3) | C9—C8—C14—C13 | 43.2 (3) |
C9—C5—C6—C7 | −42.0 (3) | C7—C8—C14—C15 | −73.7 (3) |
C5—C6—C7—C8 | 32.1 (3) | C9—C8—C14—C15 | 167.3 (2) |
C6—C7—C8—C14 | −132.6 (2) | C12—C13—C14—C8 | −61.2 (3) |
C6—C7—C8—C9 | −8.9 (3) | C17—C13—C14—C8 | 177.8 (2) |
C10—C5—C9—C11 | −73.7 (3) | C18—C13—C14—C8 | 61.6 (3) |
C4—C5—C9—C11 | 50.4 (3) | C12—C13—C14—C15 | 167.0 (2) |
C6—C5—C9—C11 | 169.1 (2) | C17—C13—C14—C15 | 45.9 (3) |
C10—C5—C9—C8 | 153.5 (2) | C18—C13—C14—C15 | −70.2 (3) |
C4—C5—C9—C8 | −82.4 (3) | C8—C14—C15—C16 | −160.7 (2) |
C6—C5—C9—C8 | 36.3 (2) | C13—C14—C15—C16 | −31.3 (3) |
C14—C8—C9—C11 | −26.5 (3) | C14—C15—C16—C17 | 3.9 (3) |
C7—C8—C9—C11 | −149.4 (2) | C15—C16—C17—O21 | 151.9 (3) |
C14—C8—C9—C5 | 105.5 (2) | C15—C16—C17—C13 | 24.7 (3) |
C7—C8—C9—C5 | −17.4 (3) | C12—C13—C17—O21 | 74.7 (3) |
C2—C1—C10—O19 | −149.7 (3) | C14—C13—C17—O21 | −169.7 (2) |
C2—C1—C10—C5 | 32.7 (4) | C18—C13—C17—O21 | −51.2 (3) |
C4—C5—C10—O19 | −158.1 (3) | C12—C13—C17—C16 | −158.7 (2) |
C6—C5—C10—O19 | 79.6 (3) | C14—C13—C17—C16 | −43.2 (2) |
C9—C5—C10—O19 | −31.9 (4) | C18—C13—C17—C16 | 75.3 (3) |
C4—C5—C10—C1 | 19.5 (3) |