Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618000037/yf3132sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000037/yf3132Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000037/yf3132Isup3.cml |
CCDC reference: 1814275
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C28H28N2O2 | F(000) = 1808 |
Mr = 424.52 | Dx = 1.240 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.3641 (8) Å | Cell parameters from 10436 reflections |
b = 10.0825 (3) Å | θ = 2.2–27.6° |
c = 21.4524 (7) Å | µ = 0.08 mm−1 |
β = 115.885 (1)° | T = 100 K |
V = 4546.5 (3) Å3 | Block, colourless |
Z = 8 | 0.15 × 0.15 × 0.12 mm |
Bruker D8 Venture diffractometer | 10435 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 7625 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.050 |
φ and ω scans | θmax = 27.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −30→30 |
Tmin = 0.967, Tmax = 0.991 | k = −13→11 |
35190 measured reflections | l = −27→24 |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0485P)2 + 1.7906P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
10435 reflections | Δρmax = 0.30 e Å−3 |
588 parameters | Δρmin = −0.29 e Å−3 |
Experimental. Spectroscopic characterization for compounds (Ia–d), (IIa–d) and (IIIa–d). (Ia), IR (ATR, cm-1) 3421 (N—H), 1741 [C=O (ester)], 1635 [C=C (allyl)], 918 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 3.43 (d, J = 6.2 Hz, 2H, –CH2–), 3.73 (s, 3H, OCH3), 5.12 (s, 1H, N—CH), 5.16 (s, 1H, N—H), 5.23 (dq, J = 10.0, 1.6 Hz, 1H, =CH2 (H-cis)), 5.26 (dq, J = 17.2, 1.6 Hz, 1H, =CH2 (H-trans)), 6.01 (ddt, J = 17.2, 10.0, 6.2 Hz, 1H, =CH–), 6.35 (d, J = 7.6 Hz, 1H, 6'-H), 6.69 (td, J = 7.4, 0.8 Hz, 1H, 4'-H), 7.01 (td, J = 7.6, 1.2 Hz, 1H, 5'-H), 7.08 (dd, J = 7.2, 1.2 Hz, 1H, 3'-H), 7.28–7.32 (m, 1H, 4-H), 7.33–7.37 (m, 2H, 3-H, 5-H), 7.46–7.49 (m, 2H, 2-H, 6-H), δ(13C) 36.8 (–CH2–), 52.9 (OCH3), 60.5 (N—CH–), 111.3 (6'-C), 116.7 (=CH2), 117.8 (4'-C), 124.1 (2'-C), 127.2 (2-C, 6-C), 127.6 (5'-C), 128.3 (4-C), 128.9 (3-C, 5-C), 130.0 (3'-C), 135.7 (=CH–), 137.6 (1-C), 144.0 (1'-C), 172.4 (C=O); GC—MS (70 eV) m/z (%) 281 (M+, 20), 223 (24), 222 (100), 130 (21), 91 (27). (Ib), IR (ATR, cm-1) 3382 (N—H), 1739 [C=O (ester)], 1635 [C=C (allyl)], 925 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 2.20 (s, 3H, 4'-CH3), 3.40 (dt, J = 6.4, 1.6 Hz, 2H, –CH2–), 3.73 (s, 3H, OCH3), 5.01 (d, J = 6.0 Hz, 1H, N—H), 5.09 (d, J = 6.0 Hz, 1H, N—CH), 5.22 (dq, J = 10.0, 1.6 Hz, 1H, =CH2 (H-cis)), 5.25 (dq, J = 16.8, 1.6 Hz, 1H, =CH2 (H-trans)), 6.00 (ddt, J = 16.8, 10.0, 6.4 Hz, 1H, =CH–), 6.27 (d, J = 8.0 Hz, 1H, 6'-H), 6.81 (dd, J = 8.0, 1.8 Hz, 1H, 5'-H), 6.90 (d, J = 1.8 Hz, 1H, 3'-H), 7.28–7.30 (m, 1H, 4-H), 7.31–7.37 (m, 2H, 3-H, 5-H), 7.46–7.49 (m, 2H, 2-H, 6-H), δ(13C) 20.4 (4'-CH3), 36.8 (–CH2–), 52.8 (OCH3), 60.8 (N—CH–), 111.4 (6'-C), 116.6 (=CH2), 124.2 (2'-C), 127.0 (4'-C), 127.2 (2-C, 6-C), 127.9 (5'-C), 128.2 (4-C), 128.8 (3-C, 5-C), 130.9 (3'-C), 135.9 (=CH–), 137.8 (1-C), 141.7 (1'-C), 172.6 (C=O); GC—MS (70 eV) m/z (%) 295 (M+, 27), 237 (26), 236 (100), 144 (25), 91 (18). (Ic), IR (ATR, cm-1) 3406 (NH), 1733 [C=O (ester)], 1634 [C=C (allyl)], 929 [=CH (allyl)]; NMR (CDCl3) δ(1H) 3.38 (dt, J = 6.4, 1.6 Hz, 2H, –CH2–), 3.73 (s, 3H, OCH3) 5.06 (d, J = 6.0 Hz, 1H, N—CH), 5.15 (d, J = 5.8 Hz, 1H, N—H), 5.24–5.29 (m, 2H, =CH2), 5.92–6.02 (m, 1H, =CH–), 6.24 (d, J = 8.4 Hz, 1H, 6'-H), 6.94 (dd, J = 8.4, 2.4 Hz, 1H, 5'-H), 7.05 (d, J = 2.4 Hz, 1H, 3'-H), 7.29–7.38 (m, 3H, 3-H, 4-H, 5-H), 7.43–7.46 (m, 2H, 2-H, 6-H), δ(13C) 36.5 (–CH2–), 52.9 (OCH3), 60.5 (N—CH–), 112.3 (6'-C), 117.4 (=CH2), 122.4 (4'-C), 125.8 (2'-C), 127.2 (5'-C, 2-C, 6-C), 128.5 (4-C), 129.0 (3-C, 5-C), 129.7 (3'-C), 134.8 (=CH–), 137.2 (1-C), 142.4 (1'-C), 172.1 (C=O); GC– MS (70 eV) m/z (%) 315 (M+, 35Cl, 20), 258 (33), 257 (22), 256 (100), 164 (13), 91 (24). (Id), IR (ATR, cm-1) 3420 (N—H), 1735 [C=O (ester)], 1636 [C=C (allyl)], 927 [=C—H (allyl)]; NMR (CDCl3) δ1H) 2.14 (s, 3H, 5-CH3), 2.25 (s, 3H, 3'-CH3), 3.43 (br d, J = 5.8 Hz, 2H, –CH2–), 3.73 (s, 3H, OCH3), 5.10 (s, 1H, N—CH), 5.16 (dq, J = 10.0, 1.6 Hz, 1H, =CH2 (H-cis)), 5.17 (dq, J = 17.0, 1.6 Hz, 1H, =CH2 (H-trans)), 5.96 (ddt, J = 17.0, 10.0, 5.8 Hz, 1H, =CH–), 6.09 (s, 1H, 6'-H), 6.44 (s, 1H, 4'-H), 7.28–7.32 (m, 1H, 4-H), 7.33–7.37 (m, 2H, 3-H, 5-H), 7.46–7.49 (m, 2H, 2-H, 6-H), δ(13C) 20.1 (3'-CH3), 21.5 (5'-CH3), 31.6 (–CH2–), 52.8 (OCH3), 60.7 (N—CH–), 110.3 (6'-C), 115.7 (=CH2), 119.4 (2'-C), 121.1 (4'-C), 127.2 (2-C, 6-C), 128.2 (4-C), 128.8 (3-C, 5-C), 134.9 (=CH–), 136.4 (5'-C), 136.9 (3'-C), 137.9 (1-C), 144.1 (1'-C), 172.6 (C=O); GC—MS (70 eV): m/z (%) 309 (M+, 26), 251 (26), 250 (100), 158 (30). (IIa), IR (ATR, cm-1) 1744 [C=O (ester)], 1664 [C=O (amide)], 1600 [C=C (allyl)], 920 [=C—H (allyl)]; NMR (CDCl3) δ1H) 2.78 (ddt, J = 15.6, 5.7, 1.5 Hz, 1H, –CHAHB–), 3.07 (dd, J = 15.6, 7.8 Hz, 1H, –CHAHB–), 3.72 (d, J = 14.0 Hz, 1H, –CHAHB—Cl), 3.76 (s, 3H, OCH3), 3.81 (d, J = 14.0 Hz, 1H, –CHAHB—Cl), 4.98 (dq, J = 17.0, 1.6 Hz, 1H, =CH2 (H-trans)), 5.03 (dq, J = 10.1, 1.6 Hz, 1H, =CH2 (H-cis)), 5.44 (dddd, J = 17.0, 10.1, 7.8, 5.8 Hz, 1H, =CH–), 6.01 (s, 1H, N—CH), 7.01–7.04 (m, 3H, 3'-H, 2''-H, 6''-H), 7.10–7.15 (m, 2H, 3''-H, 5''-H), 7.18–7.24 (m, 3H, 4'-H, 5'-H, 4''-H), 7.64–7.74 (m, 1H, 6'-H), δ(13C) 35.1 (–CH2–), 42.6 (CH2Cl), 52.7 (OCH3), 65.0 (N—CH–), 117.3 (=CH2), 127.4 (5'-C), 128.2 (3''-C, 5''-C), 128.8 (4''-C), 129.6 (4'-C), 130.2 (3'-C), 130.6 (2''-C, 6''-C), 131.2 (6'-C), 131.8 (1''-C), 135.3 (=CH–), 136.2 (1'-C), 139.0 (2'-C), 167.1 (N—C=O), 170.6 (C=O); GC—MS (70 eV) m/z (%) 357 (M+, 35Cl, 4), 298 (61), 222 (100), 208 (64), 149 (35), 132 (20), 130 (44), 121 (69), 91 (62), 77 (40). (IIb), IR (ATR, cm-1) 1746 [C=O (ester)], 1673 [C=O (amide)], 1598 [C=C (allyl)], 919 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 2.26 (s, 3H, 4'-CH3), 2.70 (dd, J = 15.6, 5.6 Hz, 1H, –CHAHB–), 3.00 (dd, J = 15.6, 8.0 Hz, 1H, –CHAHB–), 3.71 (d, J = 14.1 Hz, 1H, –CHAHB—Br), 3.74 (s, 3H, OCH3), 3.82 (d, J = 14.1 Hz, 1H, –CHAHB—Br), 4.95–5.02 (m, 2H, =CH2), 5.35–5.45 (m, 1H, =CH–), 5.98 (s, 1H, N—CH), 6.81 (s, 1H, 3'-H), 7.01–7.03 (m, 3H, 5'-H, 2''-H, 6''-H), 7.11–7.15 (m, 2H, 3''-H, 5''-H), 7.19–7.23 (m, 1H, 4''-H), 7.53 (d, J = 8.0 Hz, 1H, 6'-H), δ(13C) 21.2 (4'-CH3), 35.1 (–CH2–), 42.8 (–CH2Br), 52.7 (OCH3), 65.0 (N—CH–), 117.2 (=CH2), 128.2 (5'-C, 3''-C, 5''-C), 128.8 (4''-C), 130.7 (2''-C, 6''-C), 130.8 (3'-C, 6'-C), 131.9 (1''-C), 133.5 (1'-C), 135.6 (=CH–), 138.4 (2'-C), 139.7 (4'-C), 167.4 (N—CO–), 170.7 (C=O); GC—MS (70 eV) m/z (%) 415 (M++, 79Br, 13), 356 (35), 266 (35), 236 (100), 149 (31), 146 (22), 144 (39), 121 (46), 91 (38), 77 (22). (IIc), IR (ATR, cm-1) 1739 [C=O (ester)], 1674 [C=O (amide)], 1643 [C=C (allyl)], 920 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 2.71 (dd, J = 15.7, 5.8 Hz, 1H, –CHAHB–), 3.02 (dd, J = 15.7, 7.7 Hz, 1H, –CHAHB–), 3.70 (d, J = 13.8 Hz, 1H, –CHAHB—Cl), 3.75 (s, 3H, OCH3), 3.78 (d, J = 13.8 Hz, 1H, –CHAHB—Cl), 5.00 (dq, J = 17.0, 1.6 Hz, 1H, =CH2 (H-trans)), 5.07 (dq, J = 10.0, 1.5 Hz, 1H, =CH2 (H-cis)), 5.37 (dddd, J = 17.0, 10.0, 7.7, 5.8 Hz, 1 H, =CH–), 6.04 (s, 1H, N—CH), 7.01 (s, 1H, 3'-H), 6.99–7.02 (m, 2H, 2''-H, 6''-H), 7.14–7.18 (m, 2H, 3''-H, 5''-H), 7.23 (dd, J = 8.5, 1.8 Hz, 1H, 5'-H), 7.23–7.26 (m, 1H, 4''-H), 7.71 (d, J = 8.5 Hz, 1H, 6'-H), δ(13C) 35.0 (–CH2–), 42.3 (–CH2Cl), 52.7 (OCH3), 64.8 (N—CH–), 118.2 (=CH2), 127.6 (5'-C), 128.4 (3''-C, 5''-C), 129.1 (4''- C), 130.1 (3'-C), 130.6 (2''-C, 6''-C), 131.5 (1''-C), 132.6 (6'-C), 134.4 (=CH–), 134.7 (1'-C), 135.5 (4'-C), 141.1 (2'-C), 167.1 (N—CO–), 170.6 (C=O); GC—MS (70 eV), m/z (%) 391 (M+, 35Cl, 12), 332 (62), 256 (100), 242 (50), 166 (22), 164 (28), 149 (55), 121 (78), 91 (52), 77 (45); HR—MS (EI—MS, 70 eV) m/z found 391.0737, C20H1935Cl2NO3 requires 391.0742. (IId), IR (ATR, cm-1) 1742 [C=O (ester)], 1672 [C=O (amide)], 1610 [C=C (allyl)], 922 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 2.09 (s, 3H, 3'-CH3), 2.25 (s, 3H, 5'-CH3), 2.89–2.95 (m, 1H, –CHAHB–), 3.13 (dd, J = 15.9, 7.0 Hz, 1H, –CHAHB–), 3.76 (s, 3H, OCH3), 3.77 (d, J = 14.1 Hz, 1H, –CHAHB—Cl), 3.80 (d, J = 14.1 Hz, 1H, –CHAHB—Cl), 4.85 (dq, J = 17.1, 1.6 Hz, 1H, =CH2 (H-trans)), 4.99 (dq, J = 10.1, 1.6 Hz, 1H, =CH2 (H-cis)), 5.59 (dddd, J = 17.1, 10.1, 7.0, 4.8 Hz, 1H, =CH–), 5.74 (s, 1H, N—CH), 6.93 (s, 1H, 4'-H), 7.05–7.08 (m, 2H, 2''-H, 6''-H), 7.15 (s, 1H, 6'-H), 7.12–7.16 (m, 2H, 3''-H, 5''-H), 7.18–7.21 (m, 1H, 4''-H), δ(13C) 19.6 (3'-CH3), 20.7 (5'-CH3), 32.5 (–CH2–), 43.0 (–CH2Cl), 52.6 (OCH3), 65.6 (N—CH–), 116.1 (=CH2), 128.0 (3''-C, 5''-C), 128.7 (4''-C), 129.1 (6'-C), 130.3 (1''-C), 130.6 (2''-C, 6''-C), 132.3 (5'-C), 132.4 (4'-C), 133.4 (2'-C), 134.6 (=CH–), 136.9 (1'-C), 138.6 (3'-C), 167.2 (N—CO–), 170.3 (C=O); GC—MS (70 eV) m/z (%) 385 (M+, 35Cl, 13), 326 (36), 250 (83), 236 (92), 160 (72), 158 (100), 149 (83), 121 (88), 91 (58), 77 (58); HR—MS (EI—MS, 70 eV) m/z found 385.1440, C22H2435ClNO3 requires 385.1445. (IIIa), IR (ATR, cm-1) 1686/1676 [C=O (lactam)], 1599 [C=C (allyl)], 930 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 3.36 (d, J = 6.5 Hz, 2H, –CH2–), 4.00 (d, J = 17.7 Hz, 1H, 6-HAHB), 4.21 (d, J = 17.7 Hz, 1H, 6-HAHB), 4.62 (s, 2H, N—CH2–), 5.04 (dd, J = 17.1, 1.4 Hz, 1H, =CH2 (H-trans)), 5.11 (dd, J = 10.0, 1.4 Hz, 1H, =CH2 (H-cis)), 5.15 (s, 1H, 3-H), 6.78 (d, J = 7.9 Hz, 1H, 6'-H), 5.92 (ddt, J = 17.1, 10.0, 6.5 Hz, 1H, =CH–), 7.07 (td, J = 7.9, 1.5 Hz, 1H, 5'-H), 7.15–7.18 (m, 2H, 2'''-H, 6'''-H), 7.24–7.28 (m, 1H, 4'-H), 7.29–7.32 (m, 4H, 3'-H, 3'''-H, 5'''-H, 4'''-H), 7.36–7.40 (m, 5H, 2''-H, 6''-H, 3''-H, 5''-H, 4''-H), δ(13C) 36.0 (–CH2–), 49.5 (N—CH2–), 49.6 (6-C), 68.1 (3-C), 116.8 (=CH2), 126.8 (2''-C, 6''-C), 127.3 (5'-C), 128.2 (2'''-C, 6'''-C, 4'''-C, 6'-C), 128.9 (4'-C, 4''-C, 3'''-C, 5'''-C), 129.2 (3''-C, 5''-C), 130.9 (3'-C), 135.1 (1'''-C), 135.8 (=CH–), 136.0 (1''-C), 136.6 (2'-C), 137.8 (1'-C), 164.6 (5-C=O), 165.2 (2-C=O); GC—MS (70 eV) m/z (%) 396 (M+, 23), 248 (12), 220 (37), 172 (6), 118 (46), 91 (100), 77 (11); HR—MS (EI—MS, 70 eV) m/z found 396.1838, C26H24N2O2 requires 396.1836. (IIIb), IR (ATR, cm-1) 1665 [C=O (lactam)], 1608 [C=C (ally)], 916 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 2.28 (s, 3H, 4'-CH3), 3.32 (br d, J = 6.8 Hz, 2H, –CH2–), 4.01 (d, J = 18.0 Hz, 1H, 6-HAHB), 4.22 (d, J = 18.0 Hz, 1H, 6-HAHB), 4.59 (d, J = 14.6 Hz, 1H, N—CHAHB–), 4.64 (d, J = 14.6 Hz, 1H, N—CHAHB–), 5.04 (dq, J = 17.2, 1.6 Hz, 1H, =CH2 (H-trans)), 5.10 (dq, J = 10.0, 1.6 Hz, 1H, =CH2 (H-cis)), 5.13 (s, 1H, 3-H), 5.91 (ddt, J = 17.2, 10.0, 6.8 Hz, 1H, =CH–), 6.64 (d, J = 8.0 Hz, 1H, 6'-H), 6.87 (dd, J = 8.0, 1.6 Hz, 1H, 5'-H), 7.11 (d, J = 1.6 Hz, 1H, 3'-H), 7.16–7.18 (m, 2H, 2'''-H, 6'''-H), 7.29- 7.32 (m, 3H, 3'''-H, 5'''-H, 4'''-H), 7.38–7.41 (m, 5H, 2''-H, 6''-H, 3''-H, 5''-H, 4''-H), δ(13) 21.1 (4'-CH3), 36.1 (–CH2–), 49.5 (N—CH2–), 49.6 (6-C), 68.1 (3-C), 116.7 (=CH2), 126.9 (2''-C, 6''-C), 128.0 (4'''-C), 128.1 (6'-C), 128.2 (4'''-C), 128.3 (2'''-C, 6'''-C), 128.5 (5'-C), 128.9 (4''-C), 129.0 (3'''-C, 5'''-C), 129.2 (3''-C, 5''-C), 131.7 (3'-C), 135.1 (1'-C), 135.2 (1'''-C), 136.0 (=CH–), 136.1 (1''-C), 136.3 (2'-C), 139.0 (4'-C), 164.7 (5-C=O), 165.3 (2-C=O); GC—MS (70 eV) m/z (%) 410 (M+, 91), 262 (16), 234 (50), 186 (6), 118 (44), 91 (100), 77 (7). (IIIc), IR (ATR, cm-1) 1661 [C=O (lactam)], 1597 [C=C (allyl)], 919 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 3.32 (br d, J = 6.5 Hz, 2H, –CH2–), 4.00 (d, J = 17.8 Hz, 1H, 6-HAHB), 4.21 (d, J = 17.8 Hz, 1H, 6-HAHB), 4.59 (d, J = 14.6 Hz, 1H, N—CHAHB–), 4.64 (d, J = 14.6 Hz, 1H, N—CHAHB–), 5.07 (dq, J = 17.1, 1.5 Hz, 1H, =CH2 (H-trans)), 5.10 (s, 1H, 3-H), 5.15 (dq, J = 10.1, 1.5 Hz, 1H, =CH2 (H-cis)), 5.88 (ddt, J = 17.1, 10.1, 6.5 Hz, 1H, =CH–), 6.68 (d, J = 8.5 Hz, 1H, 6'-H), 7.03 (dd, J = 8.5, 2.4 Hz, 1H, 5'-H), 7.15–7.18 (m, 2H, 2'''-H, 6'''-H), 7.30 (d, J = 2.4 Hz, 1H, 3'-H), 7.28–7.31 (m, 2H, 3'''-H, 5'''-H), 7.34–7.37 (m, 3H, 2''-H, 6''-H, 4''-H), 7.39–7.42 (m, 3H, 3''-H, 5''-H, 4'''-H), δ(13C) 35.8 (–CH2–), 49.5 (N—CH2–), 49.6 (6-C), 68.0 (3-C), 117.6 (=CH2), 126.8 (2''-C, 6''-C), 127.5 (5'-C), 128.2 (2'''-C, 6'''-C, 4'''-C), 129.0 (3'''-C, 5'''-C), 129.1 (4''-C), 129.3 (3''-C, 5''-C), 129.5 (6'-C), 130.9 (3'-C), 134.7 (4'-C), 134.8 (=CH–), 135.0 (1'''-C), 135.8 (1''-C), 136.2 (1'-C), 138.8 (2'-C), 164.5 (5-C=O), 164.9 (2-C=O); GC—MS (70 eV) m/z (%) 430 (M+, 35Cl, 20), 282 (8), 254 (25), 218 (5), 118 (42), 91 (100), 77 (4). (IIId), IR (ATR, cm-1) 1665 [C=O (lactam)], 1613 [C=C (allyl)], 900 [=C—H (allyl)]; NMR (CDCl3) δ(1H) 2.08 (s, 3H, 5'-CH3), 2.29 (s, 3H, 3'-CH3), 3.26–3.37 (m, 2H, –CH2–), 4.00 (d, J = 17.7 Hz, 1H, 6-HAHB), 4.22 (d, J = 17.7 Hz, 1H, 6-HAHB), 4.57 (d, J = 14.6 Hz, 1H, N—CHAHB–), 4.66 (d, J = 14.6 Hz, 1H, N—CHAHB–), 4.89 (dq, J = 17.1, 1.6 Hz, 1H, =CH2 (H-trans)), 5.15 (s, 1H, 3-H), 5.07 (dq, J = 10.2, 1.6 Hz, 1H, =CH2 (H-cis)), 5.83–5.93 (m, 1H, =CH–), 6.42 (s, 1H, 6'-H), 6.96 (s, 1H, 4'-H), 7.16–7.19 (m, 2H, 2'''-H, 6'''-H), 7.28–7.32 (m, 3H, 3'''-H, 5'''-H, 4'''-H), 7.35–7.40 m, 5H, 2''-H, 6''-H, 3''-H, 5''-H, 4''-H), δ(13C) 19.8 (3'-CH3), 20.7 (5'-CH3), 32.3 (–CH2–), 49.5 (N—CH2–), 49.6 (6-C), 68.2 (3-C), 115.9 (=CH2), 126.9 (6'-C), 127.0 (2''-C, 6''-C), 128.1 (4'''-C), 128.2 (2'''-C, 6'''-C), 128.8 (4''-C), 128.9 (5'''-C, 3'''-C), 129.1 (3''-C, 5''-C), 131.4 (2'-C), 131.9 (4'-C), 135.1 (=CH–), 135.2 (1'''-C), 136.1 (1''-C), 136.6 (5'-C), 137.9 (1'-C), 138.7 (3'-C), 164.7 (5-C=O), 165.3 (2-C=O); GC—MS (70 eV) m/z (%) 424 (M+, 24), 276 (12), 248 (35), 200 (6), 118 (43), 91 (100), 77 (9); HR—MS (EI—MS, 70 eV) m/z found 424.2145, C28H28N2O2 requires 424.2151. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N11 | 0.49184 (6) | 0.79569 (12) | 0.63445 (7) | 0.0160 (3) | |
C12 | 0.43177 (7) | 0.81150 (15) | 0.58557 (8) | 0.0158 (3) | |
O12 | 0.41013 (5) | 0.75649 (11) | 0.52881 (6) | 0.0217 (3) | |
C13 | 0.38860 (7) | 0.90236 (14) | 0.60278 (8) | 0.0151 (3) | |
H13 | 0.3619 | 0.9523 | 0.5595 | 0.018* | |
N14 | 0.42363 (6) | 1.00168 (12) | 0.65606 (6) | 0.0143 (3) | |
C15 | 0.48274 (7) | 0.98184 (14) | 0.70731 (8) | 0.0145 (3) | |
O15 | 0.50869 (5) | 1.05941 (10) | 0.75554 (6) | 0.0207 (3) | |
C16 | 0.51692 (7) | 0.85789 (15) | 0.70279 (8) | 0.0159 (3) | |
H16B | 0.5622 | 0.8801 | 0.7172 | 0.019* | |
H16A | 0.5152 | 0.7923 | 0.7363 | 0.019* | |
C117 | 0.53437 (7) | 0.70366 (15) | 0.62255 (9) | 0.0192 (3) | |
H11A | 0.5088 | 0.6461 | 0.5826 | 0.023* | |
H11B | 0.5552 | 0.6460 | 0.6638 | 0.023* | |
C111 | 0.58541 (7) | 0.77210 (16) | 0.60834 (8) | 0.0196 (3) | |
C112 | 0.63616 (8) | 0.6971 (2) | 0.61018 (10) | 0.0324 (4) | |
H112 | 0.6385 | 0.6053 | 0.6211 | 0.039* | |
C113 | 0.68315 (9) | 0.7544 (2) | 0.59640 (12) | 0.0437 (5) | |
H113 | 0.7175 | 0.7021 | 0.5978 | 0.052* | |
C114 | 0.68015 (9) | 0.8876 (2) | 0.58055 (11) | 0.0429 (5) | |
H114 | 0.7124 | 0.9269 | 0.5709 | 0.051* | |
C115 | 0.63028 (9) | 0.9640 (2) | 0.57873 (10) | 0.0344 (5) | |
H115 | 0.6285 | 1.0559 | 0.5683 | 0.041* | |
C116 | 0.58286 (8) | 0.90604 (17) | 0.59213 (9) | 0.0237 (4) | |
H116 | 0.5483 | 0.9585 | 0.5902 | 0.028* | |
C131 | 0.34310 (7) | 0.82154 (14) | 0.62156 (8) | 0.0161 (3) | |
C132 | 0.36518 (8) | 0.75635 (16) | 0.68476 (9) | 0.0212 (4) | |
H132 | 0.4090 | 0.7613 | 0.7163 | 0.025* | |
C133 | 0.32378 (8) | 0.68403 (16) | 0.70228 (9) | 0.0246 (4) | |
H133 | 0.3393 | 0.6398 | 0.7457 | 0.029* | |
C134 | 0.26005 (8) | 0.67634 (16) | 0.65668 (10) | 0.0264 (4) | |
H134 | 0.2316 | 0.6278 | 0.6689 | 0.032* | |
C135 | 0.23773 (8) | 0.73922 (16) | 0.59335 (10) | 0.0274 (4) | |
H135 | 0.1940 | 0.7331 | 0.5618 | 0.033* | |
C136 | 0.27918 (7) | 0.81169 (16) | 0.57552 (9) | 0.0224 (4) | |
H136 | 0.2637 | 0.8545 | 0.5317 | 0.027* | |
C141 | 0.38972 (7) | 1.12302 (14) | 0.65377 (8) | 0.0155 (3) | |
C142 | 0.39739 (7) | 1.23103 (15) | 0.61735 (8) | 0.0191 (3) | |
C143 | 0.36172 (8) | 1.34625 (15) | 0.61338 (9) | 0.0232 (4) | |
C144 | 0.32063 (8) | 1.34677 (16) | 0.64436 (9) | 0.0247 (4) | |
H144 | 0.2963 | 1.4245 | 0.6406 | 0.030* | |
C145 | 0.31321 (7) | 1.23918 (16) | 0.68074 (9) | 0.0217 (4) | |
C146 | 0.34888 (7) | 1.12590 (15) | 0.68533 (8) | 0.0178 (3) | |
H146 | 0.3453 | 1.0506 | 0.7100 | 0.021* | |
C147 | 0.36800 (10) | 1.46881 (17) | 0.57627 (10) | 0.0371 (5) | |
H17A | 0.3349 | 1.5328 | 0.5720 | 0.056* | |
H17B | 0.3632 | 1.4444 | 0.5300 | 0.056* | |
H17C | 0.4100 | 1.5087 | 0.6028 | 0.056* | |
C148 | 0.26633 (9) | 1.24471 (19) | 0.71168 (11) | 0.0348 (5) | |
H18A | 0.2682 | 1.1616 | 0.7362 | 0.052* | |
H18B | 0.2233 | 1.2570 | 0.6747 | 0.052* | |
H18C | 0.2771 | 1.3191 | 0.7443 | 0.052* | |
C151 | 0.44283 (8) | 1.22442 (18) | 0.58450 (10) | 0.0307 (4) | 0.534 (4) |
H15A | 0.4605 | 1.1337 | 0.5896 | 0.037* | 0.534 (4) |
H15B | 0.4196 | 1.2441 | 0.5344 | 0.037* | 0.534 (4) |
C152 | 0.49575 (17) | 1.3211 (4) | 0.6175 (2) | 0.0235 (7) | 0.534 (4) |
H152 | 0.4935 | 1.3842 | 0.6493 | 0.028* | 0.534 (4) |
C153 | 0.5461 (7) | 1.322 (3) | 0.6037 (7) | 0.057 (3) | 0.534 (4) |
H15C | 0.5490 | 1.2593 | 0.5721 | 0.068* | 0.534 (4) |
H15D | 0.5792 | 1.3847 | 0.6256 | 0.068* | 0.534 (4) |
C161 | 0.44283 (8) | 1.22442 (18) | 0.58450 (10) | 0.0307 (4) | 0.466 (4) |
H16C | 0.4426 | 1.1319 | 0.5690 | 0.037* | 0.466 (4) |
H16D | 0.4249 | 1.2803 | 0.5423 | 0.037* | 0.466 (4) |
C162 | 0.51010 (16) | 1.2639 (5) | 0.6247 (2) | 0.0235 (7) | 0.466 (4) |
H162 | 0.5327 | 1.2305 | 0.6704 | 0.028* | 0.466 (4) |
C163 | 0.5404 (8) | 1.344 (3) | 0.5997 (9) | 0.057 (3) | 0.466 (4) |
H16E | 0.5188 | 1.3790 | 0.5542 | 0.068* | 0.466 (4) |
H16F | 0.5837 | 1.3668 | 0.6275 | 0.068* | 0.466 (4) |
N21 | 0.04212 (6) | 0.63560 (12) | 0.16810 (6) | 0.0132 (3) | |
C22 | 0.09475 (7) | 0.59764 (14) | 0.16241 (8) | 0.0136 (3) | |
O22 | 0.11420 (5) | 0.64804 (10) | 0.12304 (6) | 0.0194 (2) | |
C23 | 0.13169 (7) | 0.48355 (14) | 0.21050 (8) | 0.0128 (3) | |
H23 | 0.1555 | 0.4372 | 0.1878 | 0.015* | |
N24 | 0.08851 (6) | 0.38576 (11) | 0.21790 (6) | 0.0125 (3) | |
C25 | 0.03629 (7) | 0.42531 (14) | 0.22520 (7) | 0.0129 (3) | |
O25 | 0.00104 (5) | 0.34973 (10) | 0.23653 (6) | 0.0181 (2) | |
C26 | 0.02417 (7) | 0.57354 (14) | 0.21879 (8) | 0.0152 (3) | |
H26A | −0.0216 | 0.5900 | 0.2049 | 0.018* | |
H26B | 0.0486 | 0.6154 | 0.2646 | 0.018* | |
C217 | 0.00332 (7) | 0.74618 (14) | 0.12708 (8) | 0.0143 (3) | |
H21B | 0.0243 | 0.7860 | 0.1002 | 0.017* | |
H21A | 0.0011 | 0.8150 | 0.1589 | 0.017* | |
C211 | −0.06361 (7) | 0.70544 (15) | 0.07761 (8) | 0.0148 (3) | |
C212 | −0.11271 (7) | 0.79748 (16) | 0.05874 (8) | 0.0195 (3) | |
H212 | −0.1043 | 0.8833 | 0.0790 | 0.023* | |
C213 | −0.17388 (8) | 0.76513 (18) | 0.01053 (9) | 0.0266 (4) | |
H213 | −0.2071 | 0.8287 | −0.0021 | 0.032* | |
C214 | −0.18647 (8) | 0.64005 (18) | −0.01923 (9) | 0.0283 (4) | |
H214 | −0.2283 | 0.6177 | −0.0522 | 0.034* | |
C215 | −0.13801 (8) | 0.54777 (17) | −0.00089 (9) | 0.0251 (4) | |
H215 | −0.1465 | 0.4623 | −0.0216 | 0.030* | |
C216 | −0.07709 (8) | 0.57976 (15) | 0.04761 (8) | 0.0191 (3) | |
H216 | −0.0442 | 0.5154 | 0.0606 | 0.023* | |
C231 | 0.18120 (7) | 0.53956 (14) | 0.27904 (8) | 0.0163 (3) | |
C232 | 0.17819 (8) | 0.52047 (16) | 0.34157 (8) | 0.0213 (4) | |
H232 | 0.1445 | 0.4698 | 0.3429 | 0.026* | |
C233 | 0.22437 (9) | 0.57528 (17) | 0.40248 (9) | 0.0293 (4) | |
H233 | 0.2218 | 0.5621 | 0.4450 | 0.035* | |
C234 | 0.27385 (8) | 0.64874 (17) | 0.40124 (10) | 0.0308 (4) | |
H234 | 0.3056 | 0.6851 | 0.4428 | 0.037* | |
C235 | 0.27673 (8) | 0.66881 (17) | 0.33891 (10) | 0.0283 (4) | |
H235 | 0.3103 | 0.7203 | 0.3377 | 0.034* | |
C236 | 0.23097 (7) | 0.61432 (16) | 0.27800 (9) | 0.0222 (4) | |
H236 | 0.2336 | 0.6281 | 0.2355 | 0.027* | |
C241 | 0.10316 (7) | 0.24620 (14) | 0.21712 (8) | 0.0126 (3) | |
C242 | 0.09176 (7) | 0.18795 (14) | 0.15371 (8) | 0.0133 (3) | |
C243 | 0.10867 (7) | 0.05387 (14) | 0.15368 (8) | 0.0138 (3) | |
C244 | 0.13213 (7) | −0.01712 (14) | 0.21546 (8) | 0.0143 (3) | |
H244 | 0.1428 | −0.1079 | 0.2149 | 0.017* | |
C245 | 0.14059 (7) | 0.03980 (14) | 0.27801 (8) | 0.0148 (3) | |
C246 | 0.12735 (7) | 0.17423 (14) | 0.27844 (8) | 0.0136 (3) | |
H246 | 0.1349 | 0.2169 | 0.3208 | 0.016* | |
C247 | 0.10033 (8) | −0.01281 (15) | 0.08729 (8) | 0.0193 (3) | |
H27A | 0.1123 | −0.1065 | 0.0964 | 0.029* | |
H27B | 0.1275 | 0.0309 | 0.0693 | 0.029* | |
H27C | 0.0558 | −0.0061 | 0.0531 | 0.029* | |
C248 | 0.16066 (8) | −0.04413 (16) | 0.34240 (8) | 0.0215 (4) | |
H28A | 0.1723 | 0.0136 | 0.3829 | 0.032* | |
H28B | 0.1974 | −0.0986 | 0.3481 | 0.032* | |
H28C | 0.1254 | −0.1019 | 0.3380 | 0.032* | |
C251 | 0.05832 (8) | 0.26180 (15) | 0.08601 (8) | 0.0177 (3) | |
H25A | 0.0688 | 0.3573 | 0.0943 | 0.021* | |
H25B | 0.0747 | 0.2296 | 0.0533 | 0.021* | |
C252 | −0.01264 (8) | 0.24622 (16) | 0.05317 (8) | 0.0228 (4) | |
H252 | −0.0357 | 0.2842 | 0.0086 | 0.027* | |
C253 | −0.04598 (8) | 0.18456 (19) | 0.08062 (9) | 0.0298 (4) | |
H25C | −0.0250 | 0.1451 | 0.1251 | 0.036* | |
H25D | −0.0910 | 0.1796 | 0.0559 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0155 (6) | 0.0158 (6) | 0.0174 (7) | 0.0011 (5) | 0.0077 (5) | −0.0020 (5) |
C12 | 0.0176 (8) | 0.0134 (7) | 0.0179 (8) | −0.0034 (6) | 0.0092 (6) | 0.0008 (6) |
O12 | 0.0240 (6) | 0.0223 (6) | 0.0179 (6) | −0.0037 (5) | 0.0083 (5) | −0.0058 (5) |
C13 | 0.0149 (7) | 0.0134 (7) | 0.0135 (7) | −0.0010 (6) | 0.0030 (6) | −0.0013 (6) |
N14 | 0.0127 (6) | 0.0103 (6) | 0.0162 (6) | −0.0002 (5) | 0.0029 (5) | −0.0006 (5) |
C15 | 0.0141 (7) | 0.0145 (7) | 0.0144 (7) | −0.0010 (6) | 0.0057 (6) | 0.0027 (6) |
O15 | 0.0200 (6) | 0.0168 (5) | 0.0187 (6) | −0.0002 (5) | 0.0024 (5) | −0.0039 (5) |
C16 | 0.0139 (7) | 0.0161 (7) | 0.0154 (8) | 0.0015 (6) | 0.0043 (6) | −0.0002 (6) |
C117 | 0.0212 (8) | 0.0137 (7) | 0.0247 (9) | 0.0032 (6) | 0.0119 (7) | 0.0005 (6) |
C111 | 0.0178 (8) | 0.0228 (8) | 0.0183 (8) | 0.0025 (7) | 0.0080 (6) | −0.0001 (7) |
C112 | 0.0278 (9) | 0.0375 (10) | 0.0354 (11) | 0.0086 (8) | 0.0170 (8) | 0.0039 (9) |
C113 | 0.0237 (10) | 0.0682 (15) | 0.0465 (13) | 0.0092 (10) | 0.0221 (9) | 0.0063 (11) |
C114 | 0.0262 (10) | 0.0703 (15) | 0.0367 (12) | −0.0155 (10) | 0.0180 (9) | −0.0022 (11) |
C115 | 0.0380 (11) | 0.0381 (11) | 0.0280 (10) | −0.0160 (9) | 0.0153 (8) | −0.0022 (8) |
C116 | 0.0261 (9) | 0.0235 (8) | 0.0224 (9) | −0.0014 (7) | 0.0114 (7) | −0.0003 (7) |
C131 | 0.0145 (7) | 0.0127 (7) | 0.0216 (8) | −0.0003 (6) | 0.0083 (6) | −0.0044 (6) |
C132 | 0.0169 (8) | 0.0208 (8) | 0.0239 (9) | −0.0027 (7) | 0.0070 (7) | −0.0020 (7) |
C133 | 0.0296 (9) | 0.0194 (8) | 0.0296 (10) | −0.0014 (7) | 0.0175 (8) | −0.0010 (7) |
C134 | 0.0256 (9) | 0.0174 (8) | 0.0464 (12) | −0.0024 (7) | 0.0252 (9) | −0.0048 (8) |
C135 | 0.0147 (8) | 0.0220 (8) | 0.0438 (11) | −0.0017 (7) | 0.0113 (8) | −0.0036 (8) |
C136 | 0.0176 (8) | 0.0183 (8) | 0.0272 (9) | 0.0014 (7) | 0.0060 (7) | −0.0014 (7) |
C141 | 0.0116 (7) | 0.0121 (7) | 0.0166 (8) | 0.0002 (6) | 0.0004 (6) | −0.0014 (6) |
C142 | 0.0162 (8) | 0.0155 (7) | 0.0193 (8) | −0.0028 (6) | 0.0021 (6) | 0.0017 (6) |
C143 | 0.0239 (9) | 0.0124 (7) | 0.0203 (9) | −0.0011 (6) | −0.0024 (7) | 0.0012 (6) |
C144 | 0.0219 (8) | 0.0137 (7) | 0.0266 (9) | 0.0054 (7) | −0.0004 (7) | −0.0050 (7) |
C145 | 0.0146 (7) | 0.0208 (8) | 0.0222 (9) | 0.0014 (6) | 0.0012 (6) | −0.0068 (7) |
C146 | 0.0158 (7) | 0.0143 (7) | 0.0206 (8) | −0.0017 (6) | 0.0053 (6) | −0.0008 (6) |
C147 | 0.0527 (12) | 0.0169 (8) | 0.0282 (10) | −0.0022 (8) | 0.0050 (9) | 0.0059 (7) |
C148 | 0.0270 (9) | 0.0347 (10) | 0.0453 (12) | 0.0043 (8) | 0.0182 (9) | −0.0076 (9) |
C151 | 0.0262 (9) | 0.0298 (9) | 0.0349 (11) | −0.0012 (8) | 0.0122 (8) | 0.0126 (8) |
C152 | 0.0241 (16) | 0.0234 (19) | 0.0252 (13) | 0.0036 (14) | 0.0129 (12) | 0.0007 (16) |
C153 | 0.036 (3) | 0.046 (7) | 0.097 (2) | −0.010 (4) | 0.037 (2) | −0.013 (3) |
C161 | 0.0262 (9) | 0.0298 (9) | 0.0349 (11) | −0.0012 (8) | 0.0122 (8) | 0.0126 (8) |
C162 | 0.0241 (16) | 0.0234 (19) | 0.0252 (13) | 0.0036 (14) | 0.0129 (12) | 0.0007 (16) |
C163 | 0.036 (3) | 0.046 (7) | 0.097 (2) | −0.010 (4) | 0.037 (2) | −0.013 (3) |
N21 | 0.0156 (6) | 0.0118 (6) | 0.0139 (6) | 0.0015 (5) | 0.0080 (5) | 0.0029 (5) |
C22 | 0.0155 (7) | 0.0108 (7) | 0.0140 (7) | −0.0030 (6) | 0.0059 (6) | −0.0018 (6) |
O22 | 0.0228 (6) | 0.0175 (5) | 0.0232 (6) | 0.0010 (5) | 0.0150 (5) | 0.0053 (5) |
C23 | 0.0125 (7) | 0.0106 (6) | 0.0163 (8) | −0.0004 (6) | 0.0072 (6) | 0.0006 (6) |
N24 | 0.0148 (6) | 0.0098 (6) | 0.0146 (6) | −0.0011 (5) | 0.0078 (5) | −0.0003 (5) |
C25 | 0.0158 (7) | 0.0139 (7) | 0.0091 (7) | 0.0003 (6) | 0.0054 (6) | −0.0002 (6) |
O25 | 0.0203 (5) | 0.0162 (5) | 0.0228 (6) | −0.0008 (4) | 0.0142 (5) | 0.0030 (4) |
C26 | 0.0196 (7) | 0.0134 (7) | 0.0166 (8) | 0.0029 (6) | 0.0116 (6) | 0.0026 (6) |
C217 | 0.0190 (7) | 0.0106 (7) | 0.0146 (7) | 0.0022 (6) | 0.0085 (6) | 0.0027 (6) |
C211 | 0.0190 (8) | 0.0161 (7) | 0.0121 (7) | −0.0003 (6) | 0.0095 (6) | 0.0034 (6) |
C212 | 0.0227 (8) | 0.0198 (8) | 0.0179 (8) | 0.0046 (7) | 0.0107 (7) | 0.0034 (6) |
C213 | 0.0202 (8) | 0.0333 (9) | 0.0239 (9) | 0.0077 (7) | 0.0073 (7) | 0.0088 (8) |
C214 | 0.0200 (8) | 0.0371 (10) | 0.0208 (9) | −0.0064 (8) | 0.0024 (7) | 0.0056 (8) |
C215 | 0.0292 (9) | 0.0235 (8) | 0.0212 (9) | −0.0079 (7) | 0.0096 (7) | −0.0007 (7) |
C216 | 0.0217 (8) | 0.0168 (7) | 0.0191 (8) | 0.0001 (6) | 0.0093 (7) | 0.0017 (6) |
C231 | 0.0146 (7) | 0.0107 (7) | 0.0192 (8) | 0.0025 (6) | 0.0033 (6) | 0.0016 (6) |
C232 | 0.0229 (8) | 0.0174 (8) | 0.0182 (8) | −0.0034 (7) | 0.0041 (7) | 0.0013 (6) |
C233 | 0.0356 (10) | 0.0241 (9) | 0.0183 (9) | −0.0020 (8) | 0.0026 (8) | 0.0005 (7) |
C234 | 0.0236 (9) | 0.0198 (8) | 0.0294 (10) | −0.0001 (7) | −0.0065 (7) | −0.0029 (7) |
C235 | 0.0155 (8) | 0.0207 (8) | 0.0398 (11) | −0.0027 (7) | 0.0039 (8) | −0.0006 (8) |
C236 | 0.0187 (8) | 0.0179 (8) | 0.0292 (9) | 0.0005 (7) | 0.0099 (7) | 0.0018 (7) |
C241 | 0.0111 (7) | 0.0098 (6) | 0.0174 (8) | −0.0011 (6) | 0.0067 (6) | −0.0013 (6) |
C242 | 0.0144 (7) | 0.0115 (7) | 0.0154 (8) | −0.0016 (6) | 0.0078 (6) | 0.0001 (6) |
C243 | 0.0121 (7) | 0.0123 (7) | 0.0179 (8) | −0.0030 (6) | 0.0074 (6) | −0.0023 (6) |
C244 | 0.0127 (7) | 0.0094 (6) | 0.0215 (8) | −0.0008 (6) | 0.0080 (6) | −0.0004 (6) |
C245 | 0.0115 (7) | 0.0148 (7) | 0.0175 (8) | 0.0000 (6) | 0.0057 (6) | 0.0023 (6) |
C246 | 0.0132 (7) | 0.0152 (7) | 0.0132 (7) | −0.0024 (6) | 0.0066 (6) | −0.0019 (6) |
C247 | 0.0273 (8) | 0.0141 (7) | 0.0204 (8) | −0.0004 (7) | 0.0139 (7) | −0.0024 (6) |
C248 | 0.0238 (8) | 0.0190 (8) | 0.0201 (9) | 0.0033 (7) | 0.0080 (7) | 0.0046 (6) |
C251 | 0.0287 (8) | 0.0124 (7) | 0.0138 (8) | −0.0001 (6) | 0.0109 (7) | −0.0017 (6) |
C252 | 0.0302 (9) | 0.0183 (8) | 0.0143 (8) | 0.0051 (7) | 0.0044 (7) | −0.0018 (6) |
C253 | 0.0205 (9) | 0.0392 (10) | 0.0224 (9) | 0.0004 (8) | 0.0025 (7) | −0.0022 (8) |
N11—C12 | 1.3452 (19) | C163—H16E | 0.9500 |
N11—C117 | 1.4612 (19) | C163—H16F | 0.9500 |
N11—C16 | 1.4615 (19) | N21—C22 | 1.3433 (19) |
C12—O12 | 1.2281 (18) | N21—C217 | 1.4639 (18) |
C12—C13 | 1.523 (2) | N21—C26 | 1.4657 (19) |
C13—N14 | 1.4706 (18) | C22—O22 | 1.2300 (18) |
C13—C131 | 1.527 (2) | C22—C23 | 1.535 (2) |
C13—H13 | 1.0000 | C23—N24 | 1.4678 (18) |
N14—C15 | 1.3529 (18) | C23—C231 | 1.528 (2) |
N14—C141 | 1.4468 (19) | C23—H23 | 1.0000 |
C15—O15 | 1.2256 (18) | N24—C25 | 1.3562 (19) |
C15—C16 | 1.509 (2) | N24—C241 | 1.4499 (18) |
C16—H16B | 0.9900 | C25—O25 | 1.2218 (18) |
C16—H16A | 0.9900 | C25—C26 | 1.516 (2) |
C117—C111 | 1.520 (2) | C26—H26A | 0.9900 |
C117—H11A | 0.9900 | C26—H26B | 0.9900 |
C117—H11B | 0.9900 | C217—C211 | 1.514 (2) |
C111—C116 | 1.389 (2) | C217—H21B | 0.9900 |
C111—C112 | 1.392 (2) | C217—H21A | 0.9900 |
C112—C113 | 1.382 (3) | C211—C212 | 1.391 (2) |
C112—H112 | 0.9500 | C211—C216 | 1.394 (2) |
C113—C114 | 1.379 (3) | C212—C213 | 1.389 (2) |
C113—H113 | 0.9500 | C212—H212 | 0.9500 |
C114—C115 | 1.383 (3) | C213—C214 | 1.386 (3) |
C114—H114 | 0.9500 | C213—H213 | 0.9500 |
C115—C116 | 1.389 (2) | C214—C215 | 1.383 (3) |
C115—H115 | 0.9500 | C214—H214 | 0.9500 |
C116—H116 | 0.9500 | C215—C216 | 1.385 (2) |
C131—C132 | 1.388 (2) | C215—H215 | 0.9500 |
C131—C136 | 1.388 (2) | C216—H216 | 0.9500 |
C132—C133 | 1.388 (2) | C231—C232 | 1.387 (2) |
C132—H132 | 0.9500 | C231—C236 | 1.394 (2) |
C133—C134 | 1.381 (2) | C232—C233 | 1.395 (2) |
C133—H133 | 0.9500 | C232—H232 | 0.9500 |
C134—C135 | 1.379 (3) | C233—C234 | 1.383 (3) |
C134—H134 | 0.9500 | C233—H233 | 0.9500 |
C135—C136 | 1.393 (2) | C234—C235 | 1.383 (3) |
C135—H135 | 0.9500 | C234—H234 | 0.9500 |
C136—H136 | 0.9500 | C235—C236 | 1.390 (2) |
C141—C146 | 1.391 (2) | C235—H235 | 0.9500 |
C141—C142 | 1.397 (2) | C236—H236 | 0.9500 |
C142—C143 | 1.411 (2) | C241—C246 | 1.388 (2) |
C142—C151 | 1.510 (3) | C241—C242 | 1.396 (2) |
C143—C144 | 1.386 (3) | C242—C243 | 1.408 (2) |
C143—C147 | 1.511 (2) | C242—C251 | 1.511 (2) |
C144—C145 | 1.391 (2) | C243—C244 | 1.391 (2) |
C144—H144 | 0.9500 | C243—C247 | 1.509 (2) |
C145—C146 | 1.392 (2) | C244—C245 | 1.392 (2) |
C145—C148 | 1.509 (3) | C244—H244 | 0.9500 |
C146—H146 | 0.9500 | C245—C246 | 1.391 (2) |
C147—H17A | 0.9800 | C245—C248 | 1.509 (2) |
C147—H17B | 0.9800 | C246—H246 | 0.9500 |
C147—H17C | 0.9800 | C247—H27A | 0.9800 |
C148—H18A | 0.9800 | C247—H27B | 0.9800 |
C148—H18B | 0.9800 | C247—H27C | 0.9800 |
C148—H18C | 0.9800 | C248—H28A | 0.9800 |
C151—C152 | 1.488 (3) | C248—H28B | 0.9800 |
C151—H15A | 0.9900 | C248—H28C | 0.9800 |
C151—H15B | 0.9900 | C251—C252 | 1.500 (2) |
C152—C153 | 1.333 (11) | C251—H25A | 0.9900 |
C152—H152 | 0.9500 | C251—H25B | 0.9900 |
C153—H15C | 0.9500 | C252—C253 | 1.319 (3) |
C153—H15D | 0.9500 | C252—H252 | 0.9500 |
C162—C163 | 1.333 (12) | C253—H25C | 0.9500 |
C162—H162 | 0.9500 | C253—H25D | 0.9500 |
C12—N11—C117 | 119.78 (13) | C162—C163—H16F | 120.0 |
C12—N11—C16 | 123.79 (13) | H16E—C163—H16F | 120.0 |
C117—N11—C16 | 116.25 (12) | C22—N21—C217 | 120.91 (12) |
O12—C12—N11 | 123.86 (14) | C22—N21—C26 | 121.04 (12) |
O12—C12—C13 | 118.85 (13) | C217—N21—C26 | 117.94 (12) |
N11—C12—C13 | 117.29 (13) | O22—C22—N21 | 124.88 (13) |
N14—C13—C12 | 113.29 (12) | O22—C22—C23 | 120.22 (13) |
N14—C13—C131 | 111.95 (13) | N21—C22—C23 | 114.89 (13) |
C12—C13—C131 | 110.75 (12) | N24—C23—C231 | 114.31 (12) |
N14—C13—H13 | 106.8 | N24—C23—C22 | 111.40 (11) |
C12—C13—H13 | 106.8 | C231—C23—C22 | 109.71 (11) |
C131—C13—H13 | 106.8 | N24—C23—H23 | 107.0 |
C15—N14—C141 | 120.15 (12) | C231—C23—H23 | 107.0 |
C15—N14—C13 | 123.73 (12) | C22—C23—H23 | 107.0 |
C141—N14—C13 | 116.02 (11) | C25—N24—C241 | 121.03 (12) |
O15—C15—N14 | 123.02 (14) | C25—N24—C23 | 120.69 (12) |
O15—C15—C16 | 120.14 (13) | C241—N24—C23 | 118.29 (11) |
N14—C15—C16 | 116.83 (13) | O25—C25—N24 | 123.93 (13) |
N11—C16—C15 | 115.35 (12) | O25—C25—C26 | 121.16 (13) |
N11—C16—H16B | 108.4 | N24—C25—C26 | 114.91 (12) |
C15—C16—H16B | 108.4 | N21—C26—C25 | 112.68 (12) |
N11—C16—H16A | 108.4 | N21—C26—H26A | 109.1 |
C15—C16—H16A | 108.4 | C25—C26—H26A | 109.1 |
H16B—C16—H16A | 107.5 | N21—C26—H26B | 109.1 |
N11—C117—C111 | 113.56 (13) | C25—C26—H26B | 109.1 |
N11—C117—H11A | 108.9 | H26A—C26—H26B | 107.8 |
C111—C117—H11A | 108.9 | N21—C217—C211 | 113.20 (12) |
N11—C117—H11B | 108.9 | N21—C217—H21B | 108.9 |
C111—C117—H11B | 108.9 | C211—C217—H21B | 108.9 |
H11A—C117—H11B | 107.7 | N21—C217—H21A | 108.9 |
C116—C111—C112 | 118.56 (16) | C211—C217—H21A | 108.9 |
C116—C111—C117 | 122.69 (14) | H21B—C217—H21A | 107.8 |
C112—C111—C117 | 118.74 (15) | C212—C211—C216 | 118.74 (14) |
C113—C112—C111 | 120.85 (19) | C212—C211—C217 | 119.42 (13) |
C113—C112—H112 | 119.6 | C216—C211—C217 | 121.77 (14) |
C111—C112—H112 | 119.6 | C213—C212—C211 | 120.65 (15) |
C114—C113—C112 | 120.02 (19) | C213—C212—H212 | 119.7 |
C114—C113—H113 | 120.0 | C211—C212—H212 | 119.7 |
C112—C113—H113 | 120.0 | C214—C213—C212 | 119.96 (16) |
C113—C114—C115 | 120.03 (18) | C214—C213—H213 | 120.0 |
C113—C114—H114 | 120.0 | C212—C213—H213 | 120.0 |
C115—C114—H114 | 120.0 | C215—C214—C213 | 119.88 (15) |
C114—C115—C116 | 119.88 (19) | C215—C214—H214 | 120.1 |
C114—C115—H115 | 120.1 | C213—C214—H214 | 120.1 |
C116—C115—H115 | 120.1 | C214—C215—C216 | 120.13 (16) |
C115—C116—C111 | 120.65 (17) | C214—C215—H215 | 119.9 |
C115—C116—H116 | 119.7 | C216—C215—H215 | 119.9 |
C111—C116—H116 | 119.7 | C215—C216—C211 | 120.63 (15) |
C132—C131—C136 | 119.12 (15) | C215—C216—H216 | 119.7 |
C132—C131—C13 | 120.41 (13) | C211—C216—H216 | 119.7 |
C136—C131—C13 | 120.47 (14) | C232—C231—C236 | 119.04 (14) |
C133—C132—C131 | 120.52 (15) | C232—C231—C23 | 122.87 (14) |
C133—C132—H132 | 119.7 | C236—C231—C23 | 118.09 (14) |
C131—C132—H132 | 119.7 | C231—C232—C233 | 120.39 (16) |
C134—C133—C132 | 120.07 (16) | C231—C232—H232 | 119.8 |
C134—C133—H133 | 120.0 | C233—C232—H232 | 119.8 |
C132—C133—H133 | 120.0 | C234—C233—C232 | 120.34 (18) |
C135—C134—C133 | 119.93 (16) | C234—C233—H233 | 119.8 |
C135—C134—H134 | 120.0 | C232—C233—H233 | 119.8 |
C133—C134—H134 | 120.0 | C235—C234—C233 | 119.41 (16) |
C134—C135—C136 | 120.16 (15) | C235—C234—H234 | 120.3 |
C134—C135—H135 | 119.9 | C233—C234—H234 | 120.3 |
C136—C135—H135 | 119.9 | C234—C235—C236 | 120.59 (16) |
C131—C136—C135 | 120.19 (16) | C234—C235—H235 | 119.7 |
C131—C136—H136 | 119.9 | C236—C235—H235 | 119.7 |
C135—C136—H136 | 119.9 | C235—C236—C231 | 120.21 (17) |
C146—C141—C142 | 122.62 (14) | C235—C236—H236 | 119.9 |
C146—C141—N14 | 118.89 (14) | C231—C236—H236 | 119.9 |
C142—C141—N14 | 118.43 (14) | C246—C241—C242 | 121.92 (13) |
C141—C142—C143 | 117.33 (16) | C246—C241—N24 | 119.79 (13) |
C141—C142—C151 | 120.97 (14) | C242—C241—N24 | 118.28 (13) |
C143—C142—C151 | 121.69 (15) | C241—C242—C243 | 118.03 (13) |
C144—C143—C142 | 119.27 (15) | C241—C242—C251 | 121.84 (13) |
C144—C143—C147 | 119.77 (16) | C243—C242—C251 | 120.00 (13) |
C142—C143—C147 | 120.96 (17) | C244—C243—C242 | 119.16 (14) |
C143—C144—C145 | 123.26 (15) | C244—C243—C247 | 120.33 (13) |
C143—C144—H144 | 118.4 | C242—C243—C247 | 120.50 (13) |
C145—C144—H144 | 118.4 | C243—C244—C245 | 122.51 (13) |
C144—C145—C146 | 117.53 (16) | C243—C244—H244 | 118.7 |
C144—C145—C148 | 120.68 (15) | C245—C244—H244 | 118.7 |
C146—C145—C148 | 121.75 (16) | C246—C245—C244 | 118.01 (14) |
C141—C146—C145 | 119.98 (15) | C246—C245—C248 | 121.42 (14) |
C141—C146—H146 | 120.0 | C244—C245—C248 | 120.51 (13) |
C145—C146—H146 | 120.0 | C241—C246—C245 | 120.18 (14) |
C143—C147—H17A | 109.5 | C241—C246—H246 | 119.9 |
C143—C147—H17B | 109.5 | C245—C246—H246 | 119.9 |
H17A—C147—H17B | 109.5 | C243—C247—H27A | 109.5 |
C143—C147—H17C | 109.5 | C243—C247—H27B | 109.5 |
H17A—C147—H17C | 109.5 | H27A—C247—H27B | 109.5 |
H17B—C147—H17C | 109.5 | C243—C247—H27C | 109.5 |
C145—C148—H18A | 109.5 | H27A—C247—H27C | 109.5 |
C145—C148—H18B | 109.5 | H27B—C247—H27C | 109.5 |
H18A—C148—H18B | 109.5 | C245—C248—H28A | 109.5 |
C145—C148—H18C | 109.5 | C245—C248—H28B | 109.5 |
H18A—C148—H18C | 109.5 | H28A—C248—H28B | 109.5 |
H18B—C148—H18C | 109.5 | C245—C248—H28C | 109.5 |
C152—C151—C142 | 110.9 (2) | H28A—C248—H28C | 109.5 |
C152—C151—H15A | 109.5 | H28B—C248—H28C | 109.5 |
C142—C151—H15A | 109.5 | C252—C251—C242 | 113.68 (13) |
C152—C151—H15B | 109.5 | C252—C251—H25A | 108.8 |
C142—C151—H15B | 109.5 | C242—C251—H25A | 108.8 |
H15A—C151—H15B | 108.0 | C252—C251—H25B | 108.8 |
C153—C152—C151 | 121.9 (8) | C242—C251—H25B | 108.8 |
C153—C152—H152 | 119.0 | H25A—C251—H25B | 107.7 |
C151—C152—H152 | 119.0 | C253—C252—C251 | 125.92 (15) |
C152—C153—H15C | 120.0 | C253—C252—H252 | 117.0 |
C152—C153—H15D | 120.0 | C251—C252—H252 | 117.0 |
H15C—C153—H15D | 120.0 | C252—C253—H25C | 120.0 |
C163—C162—H162 | 118.5 | C252—C253—H25D | 120.0 |
C162—C163—H16E | 120.0 | H25C—C253—H25D | 120.0 |
C117—N11—C12—O12 | −3.1 (2) | C217—N21—C22—O22 | −1.3 (2) |
C16—N11—C12—O12 | −177.96 (14) | C26—N21—C22—O22 | −177.22 (14) |
C117—N11—C12—C13 | 176.37 (13) | C217—N21—C22—C23 | 177.97 (12) |
C16—N11—C12—C13 | 1.5 (2) | C26—N21—C22—C23 | 2.07 (19) |
O12—C12—C13—N14 | −156.18 (13) | O22—C22—C23—N24 | −143.34 (14) |
N11—C12—C13—N14 | 24.34 (19) | N21—C22—C23—N24 | 37.34 (17) |
O12—C12—C13—C131 | 77.08 (17) | O22—C22—C23—C231 | 89.07 (17) |
N11—C12—C13—C131 | −102.39 (15) | N21—C22—C23—C231 | −90.25 (15) |
C12—C13—N14—C15 | −30.1 (2) | C231—C23—N24—C25 | 83.51 (16) |
C131—C13—N14—C15 | 95.98 (17) | C22—C23—N24—C25 | −41.55 (18) |
C12—C13—N14—C141 | 153.42 (13) | C231—C23—N24—C241 | −96.54 (15) |
C131—C13—N14—C141 | −80.48 (16) | C22—C23—N24—C241 | 138.40 (13) |
C141—N14—C15—O15 | 4.3 (2) | C241—N24—C25—O25 | 5.5 (2) |
C13—N14—C15—O15 | −171.99 (14) | C23—N24—C25—O25 | −174.54 (13) |
C141—N14—C15—C16 | −175.23 (13) | C241—N24—C25—C26 | −174.92 (13) |
C13—N14—C15—C16 | 8.4 (2) | C23—N24—C25—C26 | 5.03 (19) |
C12—N11—C16—C15 | −23.7 (2) | C22—N21—C26—C25 | −39.10 (19) |
C117—N11—C16—C15 | 161.20 (13) | C217—N21—C26—C25 | 144.88 (13) |
O15—C15—C16—N11 | −161.15 (14) | O25—C25—C26—N21 | −145.46 (14) |
N14—C15—C16—N11 | 18.4 (2) | N24—C25—C26—N21 | 34.96 (18) |
C12—N11—C117—C111 | 107.13 (16) | C22—N21—C217—C211 | 117.40 (15) |
C16—N11—C117—C111 | −77.60 (17) | C26—N21—C217—C211 | −66.57 (17) |
N11—C117—C111—C116 | −14.3 (2) | N21—C217—C211—C212 | 151.72 (14) |
N11—C117—C111—C112 | 167.11 (15) | N21—C217—C211—C216 | −31.5 (2) |
C116—C111—C112—C113 | 0.2 (3) | C216—C211—C212—C213 | −0.5 (2) |
C117—C111—C112—C113 | 178.85 (18) | C217—C211—C212—C213 | 176.41 (15) |
C111—C112—C113—C114 | 0.0 (3) | C211—C212—C213—C214 | 0.1 (3) |
C112—C113—C114—C115 | 0.3 (3) | C212—C213—C214—C215 | −0.1 (3) |
C113—C114—C115—C116 | −0.7 (3) | C213—C214—C215—C216 | 0.6 (3) |
C114—C115—C116—C111 | 0.9 (3) | C214—C215—C216—C211 | −1.1 (3) |
C112—C111—C116—C115 | −0.6 (3) | C212—C211—C216—C215 | 1.0 (2) |
C117—C111—C116—C115 | −179.24 (16) | C217—C211—C216—C215 | −175.84 (15) |
N14—C13—C131—C132 | −54.07 (18) | N24—C23—C231—C232 | −12.1 (2) |
C12—C13—C131—C132 | 73.40 (17) | C22—C23—C231—C232 | 113.88 (16) |
N14—C13—C131—C136 | 126.28 (15) | N24—C23—C231—C236 | 168.72 (13) |
C12—C13—C131—C136 | −106.25 (16) | C22—C23—C231—C236 | −65.33 (17) |
C136—C131—C132—C133 | −1.1 (2) | C236—C231—C232—C233 | −0.1 (2) |
C13—C131—C132—C133 | 179.29 (14) | C23—C231—C232—C233 | −179.26 (15) |
C131—C132—C133—C134 | 0.1 (2) | C231—C232—C233—C234 | −0.3 (3) |
C132—C133—C134—C135 | 0.8 (2) | C232—C233—C234—C235 | 0.8 (3) |
C133—C134—C135—C136 | −0.7 (2) | C233—C234—C235—C236 | −0.9 (3) |
C132—C131—C136—C135 | 1.2 (2) | C234—C235—C236—C231 | 0.6 (2) |
C13—C131—C136—C135 | −179.15 (15) | C232—C231—C236—C235 | −0.1 (2) |
C134—C135—C136—C131 | −0.3 (2) | C23—C231—C236—C235 | 179.17 (14) |
C15—N14—C141—C146 | −92.93 (17) | C25—N24—C241—C246 | −74.62 (18) |
C13—N14—C141—C146 | 83.67 (17) | C23—N24—C241—C246 | 105.43 (16) |
C15—N14—C141—C142 | 89.70 (18) | C25—N24—C241—C242 | 104.86 (16) |
C13—N14—C141—C142 | −93.70 (16) | C23—N24—C241—C242 | −75.09 (17) |
C146—C141—C142—C143 | 0.1 (2) | C246—C241—C242—C243 | −3.3 (2) |
N14—C141—C142—C143 | 177.34 (13) | N24—C241—C242—C243 | 177.27 (12) |
C146—C141—C142—C151 | 179.29 (15) | C246—C241—C242—C251 | 172.64 (14) |
N14—C141—C142—C151 | −3.4 (2) | N24—C241—C242—C251 | −6.8 (2) |
C141—C142—C143—C144 | −0.9 (2) | C241—C242—C243—C244 | 3.9 (2) |
C151—C142—C143—C144 | 179.89 (15) | C251—C242—C243—C244 | −172.04 (13) |
C141—C142—C143—C147 | 178.75 (15) | C241—C242—C243—C247 | −177.18 (13) |
C151—C142—C143—C147 | −0.5 (2) | C251—C242—C243—C247 | 6.8 (2) |
C142—C143—C144—C145 | 1.1 (2) | C242—C243—C244—C245 | −1.0 (2) |
C147—C143—C144—C145 | −178.53 (15) | C247—C243—C244—C245 | −179.90 (14) |
C143—C144—C145—C146 | −0.4 (2) | C243—C244—C245—C246 | −2.7 (2) |
C143—C144—C145—C148 | −178.35 (16) | C243—C244—C245—C248 | 174.56 (14) |
C142—C141—C146—C145 | 0.6 (2) | C242—C241—C246—C245 | −0.5 (2) |
N14—C141—C146—C145 | −176.65 (13) | N24—C241—C246—C245 | 178.98 (13) |
C144—C145—C146—C141 | −0.4 (2) | C244—C245—C246—C241 | 3.4 (2) |
C148—C145—C146—C141 | 177.46 (15) | C248—C245—C246—C241 | −173.81 (14) |
C141—C142—C151—C152 | −115.4 (2) | C241—C242—C251—C252 | −89.37 (17) |
C143—C142—C151—C152 | 63.7 (3) | C243—C242—C251—C252 | 86.46 (17) |
C142—C151—C152—C153 | 171.0 (12) | C242—C251—C252—C253 | 5.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C234—H234···O12 | 0.95 | 2.44 | 3.347 (2) | 160 |
C16—H16A···O15i | 0.99 | 2.44 | 3.2682 (19) | 141 |
C217—H21A···O25ii | 0.99 | 2.29 | 3.150 (2) | 144 |
C151—H15B···Cg1iii | 0.99 | 2.60 | 3.498 (2) | 151 |
C161—H16D···Cg1iii | 0.99 | 2.86 | 3.598 (2) | 122 |
C251—H25B···Cg2iv | 0.99 | 2.70 | 3.515 (2) | 139 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+1, −z. |
Parameter | Molecule 1 | Molecule 2 | Ideal boat | |
Q | 0.3302 (17) | 0.5268 (17) | ||
θ | 84.7 (3) | 88.44 (17) | 90.0 | |
φ | 126.5 (3) | 121.81 (17) | 60k | |
Cx3 | 0.322 (2) | 0.474 (2) | ||
Cx6 | 0.244 (2) | 0.438 (2) | ||
Ox2 | -0.166 (2) | -0.303 (2) | ||
Ox5 | -0.129 (2) | -0.2873 (2) | ||
Cx17 | -0.226 (3) | -0.388 (2) | ||
Cx41 | -0.333 (3) | -0.502 (2) | ||
Cx31 | 1.771 (3) | 1.988 (2) |
Ring-puckering parameters are calculated for the atom sequences Nx1—Cx2—Cx3—Nx4—Cx5—Cx6, where x = 1 or 2; for the idealised boat conformation, k represents an integer (Boeyens, 1978). |
Parameter | Molecule 1 | Molecule 2 | |
Cx2—Nx1—Cx17—Cx11 | 107.13 (16) | 117.40 (15) | |
Nx1—Cx17—Cx11—Cx12 | 167.11 (15) | 151.72 (14) | |
Nx4—Cx3—Cx31—Cx32 | -54.07 (18) | -12.1 (2) | |
Cx3—Nx4—Cx41—Cx42 | -93.70 (16) | -75.09 (17) | |
Cx41—Cx42—Cx51—Cx52 | -115.4 (2) | -89.37 (17) | |
Cx42—Cx51—Cx52—Cx53 | 171.0 (12) | 5.4 (2) | |
Cx41—Cx42—Cx51—Cx62 | -89.2 (3) | ||
Cx42—Cx51—Cx62—Cx63 | -132.9 (14) |
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