organic compounds
2-tert-Butoxy-1-phenyl-1-(2,2,6,6-tetramethylpiperidin-1-yloxy)ethane
aDepartment of Chemistry, University of Durham, South Road, Durham DH1 3LE, England
*Correspondence e-mail: a.s.batsanov@durham.ac.uk
The title compound, C21H35NO2, contains a piperidine ring in a chair conformation, with a pyramidal N atom and a single (exocyclic) N—O bond in an equatorial orientation.
Comment
Nitroxide-mediated polymerization (NMP) has emerged in recent years as a successful controlled or `living' etc.) (Matyjaszewski, 2003). Successful NMP requires the use of a monomolecular initiator, identified as an alkoxyamine, which is derived from a nitroxide. This alkoxyamine should be prepared separately and then added in a known concentration to the monomer to be polymerized. Synthetic routes to alkoxyamines include the trapping of by free nitroxides at moderate temperatures (Braslau et al., 1997; Miura et al., 1998) and a catalytic route involving Mn–salen complexes [H2salen is bis(salicylidene)ethylenediamine; Dao et al., 1998]. The title compound, (I), has been synthesized in the course of these studies (Cameron et al., 2000).
technique which can be used to prepare polymers of target molecular weight, narrow polydispersity and complex architecture (block and graft copolymers, star polymers,The molecular structure of (I) (Fig. 1) is similar in its main features to the other N-oxy-2,2,6,6-tetramethylpiperidinyl derivatives reported by Ermert & Vasella (1993), Jahn et al. (2001, 2002) and Leitich et al. (2002). The piperidine ring adopts a chair conformation with the N—O1 bond in an equatorial orientation. The N—O1 distance is typical for a single bond (Allen et al., 1987), while the N atom has pyramidal geometry, corresponding to sp3 hybridization.
Experimental
A solution of 2,2,6,6-tetramethylpiperidinyloxy (TEMPO; 0.187 g, 1.20 mmol) and di-tert-butylperoxalate (0.148 g, 0.63 mmol) in styrene (5 ml) was prepared. The mixture was degassed by three freeze/pump/thaw cycles and backflushed with argon after the final cycle. The resulting solution was sealed, then heated overnight at 313 K. After cooling, the solution was dried in vacuo to constant mass. The crude solid product obtained was then purified by flash on silica gel, eluting with a mixture of 40–60 petroleum ether/ethyl acetate (90:10 v/v). After removal of the solvent, a white crystalline solid was obtained in 79% yield. The characterization data of the isolated product were in agreement with those given in the literature (Bon et al., 1999). 1H NMR (300 MHz): δ 1.04 (s, 9H, CH3 × 3), 0.58, 1.02, 1.19, 1.37 (br s, 3H, CH3), 0.9–1.7 (br m, 6H, CH2 × 3), 3.41 (m, 1H, H1), 3.89 (m, 1H, H171), 4.74 (m, 1H, H172), 7.18–7.35 (m, 5H, Ph) p.p.m. (for the H-atom numbering, see Fig. 1).
Crystal data
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Refinement
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Methyl groups were treated as threefold symmetrical bodies rotating around C—C bonds, with a refined common Uiso for the three H atoms. Other H atoms were treated as riding on the corresponding C atoms, with refined Uiso values. C—H distances are 0.95–1.00 Å.
Data collection: SMART (Bruker, 2001); cell SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536805004976/cf6403sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805004976/cf6403Isup2.hkl
Data collection: SMART (Bruker, 2001); cell
SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.C21H35NO2 | F(000) = 1472 |
Mr = 333.50 | Dx = 1.104 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 902 reflections |
a = 15.532 (4) Å | θ = 12.1–24.3° |
b = 11.119 (3) Å | µ = 0.07 mm−1 |
c = 23.247 (5) Å | T = 100 K |
V = 4014.8 (17) Å3 | Block, colourless |
Z = 8 | 1.00 × 0.66 × 0.14 mm |
Bruker SMART 6000 CCD area-detector diffractometer | 7229 independent reflections |
Radiation source: fine-focus sealed tube | 6298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 5.6 pixels mm-1 | θmax = 32.5°, θmin = 1.8° |
ω scans | h = −23→23 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | k = −16→16 |
Tmin = 0.579, Tmax = 1.000 | l = −34→35 |
60196 measured reflections |
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)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0633P)2 + 0.7171P] where P = (Fo2 + 2Fc2)/3 |
7229 reflections | (Δ/σ)max = 0.001 |
251 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Experimental. The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of ω scans; each set at different φ and/or 2θ angles and each scan (20 sec exposure) covering 0.3° in ω. Crystal to detector distance 4.85 cm. Crystals are shattering when cut, therefore a crystal larger than the beam diameter was used and the intensities were corrected by SADABS program (actual absorption is negligible). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.50726 (3) | 0.34047 (4) | 0.41290 (2) | 0.01533 (9) | |
O2 | 0.33509 (3) | 0.38797 (5) | 0.37666 (2) | 0.01928 (10) | |
N | 0.56521 (4) | 0.25032 (5) | 0.38875 (2) | 0.01604 (10) | |
C1 | 0.43261 (4) | 0.28730 (6) | 0.43963 (3) | 0.01552 (11) | |
H1 | 0.4152 | 0.2145 | 0.4172 | 0.016 (2)* | |
C2 | 0.55469 (5) | 0.25419 (7) | 0.32449 (3) | 0.02115 (13) | |
C3 | 0.62458 (6) | 0.17267 (8) | 0.29828 (4) | 0.03198 (17) | |
H31 | 0.6109 | 0.0880 | 0.3078 | 0.040 (3)* | |
H32 | 0.6228 | 0.1808 | 0.2559 | 0.044 (3)* | |
C4 | 0.71538 (6) | 0.20006 (9) | 0.31880 (4) | 0.03276 (18) | |
H41 | 0.7564 | 0.1415 | 0.3021 | 0.044 (3)* | |
H42 | 0.7326 | 0.2818 | 0.3064 | 0.038 (3)* | |
C5 | 0.71683 (5) | 0.19182 (7) | 0.38386 (4) | 0.02631 (15) | |
H51 | 0.7755 | 0.2106 | 0.3977 | 0.032 (3)* | |
H52 | 0.7032 | 0.1083 | 0.3955 | 0.035 (3)* | |
C6 | 0.65274 (4) | 0.27758 (6) | 0.41254 (3) | 0.01839 (12) | |
C7 | 0.55652 (6) | 0.38093 (8) | 0.29805 (3) | 0.02855 (16) | |
H71 | 0.5145 (5) | 0.4323 (4) | 0.3179 (3) | 0.0386 (13)* | |
H72 | 0.5418 (5) | 0.37606 (12) | 0.2570 (3) | 0.0386 (13)* | |
H73 | 0.6144 (4) | 0.4154 (4) | 0.3024 (3) | 0.0386 (13)* | |
C8 | 0.46745 (5) | 0.19737 (8) | 0.30943 (3) | 0.02742 (15) | |
H81 | 0.4625 (2) | 0.1184 (7) | 0.3284 (3) | 0.0375 (18)* | |
H82 | 0.4632 (2) | 0.1870 (6) | 0.2674 (3) | 0.0375 (18)* | |
H83 | 0.4207 (3) | 0.2502 (5) | 0.3228 (3) | 0.0375 (18)* | |
C9 | 0.68364 (5) | 0.40811 (7) | 0.40643 (4) | 0.02434 (14) | |
H91 | 0.7018 (5) | 0.4226 (2) | 0.3668 (3) | 0.0405 (19)* | |
H92 | 0.7321 (5) | 0.4220 (2) | 0.4324 (3) | 0.0405 (19)* | |
H93 | 0.6367 (4) | 0.4628 (4) | 0.4162 (3) | 0.0405 (19)* | |
C10 | 0.65061 (5) | 0.24755 (8) | 0.47666 (3) | 0.02721 (15) | |
H101 | 0.6137 (5) | 0.3078 (6) | 0.49731 (15) | 0.0381 (18)* | |
H102 | 0.7106 (4) | 0.2503 (7) | 0.49259 (14) | 0.0381 (18)* | |
H103 | 0.6261 (5) | 0.1649 (6) | 0.48219 (6) | 0.0381 (18)* | |
C11 | 0.44530 (4) | 0.25205 (6) | 0.50208 (3) | 0.01565 (11) | |
C12 | 0.43806 (4) | 0.13184 (6) | 0.51850 (3) | 0.01924 (12) | |
H12 | 0.4270 | 0.0723 | 0.4901 | 0.025 (3)* | |
C13 | 0.44677 (5) | 0.09773 (7) | 0.57597 (3) | 0.02422 (14) | |
H13 | 0.4423 | 0.0154 | 0.5865 | 0.033 (3)* | |
C14 | 0.46198 (5) | 0.18453 (8) | 0.61768 (3) | 0.02565 (15) | |
H14 | 0.4674 | 0.1618 | 0.6569 | 0.038 (3)* | |
C15 | 0.46920 (5) | 0.30477 (7) | 0.60196 (3) | 0.02317 (14) | |
H15 | 0.4796 | 0.3642 | 0.6305 | 0.036 (3)* | |
C16 | 0.46121 (4) | 0.33830 (6) | 0.54450 (3) | 0.01906 (12) | |
H16 | 0.4666 | 0.4205 | 0.5340 | 0.025 (3)* | |
C17 | 0.36194 (4) | 0.38169 (6) | 0.43478 (3) | 0.01849 (12) | |
H171 | 0.3127 | 0.3595 | 0.4596 | 0.024 (2)* | |
H172 | 0.3840 | 0.4609 | 0.4475 | 0.024 (2)* | |
C18 | 0.26850 (4) | 0.47410 (6) | 0.36304 (3) | 0.01854 (12) | |
C19 | 0.18898 (5) | 0.45399 (8) | 0.40020 (4) | 0.02978 (17) | |
H191 | 0.1726 (3) | 0.3670 (7) | 0.3991 (3) | 0.0434 (19)* | |
H192 | 0.1403 (4) | 0.5037 (6) | 0.3852 (2) | 0.0434 (19)* | |
H193 | 0.20186 (18) | 0.4780 (7) | 0.4408 (3) | 0.0434 (19)* | |
C20 | 0.24793 (6) | 0.44747 (8) | 0.30046 (3) | 0.02784 (15) | |
H201 | 0.3015 (4) | 0.4557 (6) | 0.27679 (17) | 0.0386 (13)* | |
H202 | 0.2035 (4) | 0.5057 (6) | 0.28632 (14) | 0.0386 (13)* | |
H203 | 0.2252 (5) | 0.3634 (6) | 0.29697 (6) | 0.0386 (13)* | |
C21 | 0.30130 (6) | 0.60218 (7) | 0.36949 (4) | 0.03203 (18) | |
H211 | 0.3145 (5) | 0.6183 (3) | 0.4105 (3) | 0.045 (2)* | |
H212 | 0.2565 (4) | 0.6593 (4) | 0.3560 (3) | 0.045 (2)* | |
H213 | 0.3542 (5) | 0.6126 (2) | 0.3461 (3) | 0.045 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.01407 (19) | 0.01375 (19) | 0.0182 (2) | 0.00091 (15) | 0.00335 (15) | 0.00001 (15) |
O2 | 0.0180 (2) | 0.0243 (2) | 0.0155 (2) | 0.00446 (17) | −0.00207 (16) | 0.00068 (17) |
N | 0.0160 (2) | 0.0153 (2) | 0.0169 (2) | 0.00227 (17) | 0.00319 (17) | −0.00101 (17) |
C1 | 0.0140 (2) | 0.0174 (3) | 0.0151 (2) | −0.00090 (19) | 0.00074 (18) | 0.0011 (2) |
C2 | 0.0229 (3) | 0.0245 (3) | 0.0160 (3) | −0.0010 (2) | 0.0043 (2) | −0.0023 (2) |
C3 | 0.0312 (4) | 0.0365 (4) | 0.0283 (4) | 0.0017 (3) | 0.0104 (3) | −0.0114 (3) |
C4 | 0.0266 (4) | 0.0364 (4) | 0.0352 (4) | 0.0043 (3) | 0.0136 (3) | −0.0058 (3) |
C5 | 0.0201 (3) | 0.0224 (3) | 0.0365 (4) | 0.0065 (2) | 0.0073 (3) | 0.0021 (3) |
C6 | 0.0149 (2) | 0.0178 (3) | 0.0225 (3) | 0.0018 (2) | 0.0017 (2) | 0.0026 (2) |
C7 | 0.0322 (4) | 0.0336 (4) | 0.0199 (3) | −0.0027 (3) | 0.0016 (3) | 0.0078 (3) |
C8 | 0.0280 (3) | 0.0342 (4) | 0.0200 (3) | −0.0048 (3) | 0.0009 (3) | −0.0077 (3) |
C9 | 0.0187 (3) | 0.0198 (3) | 0.0345 (4) | −0.0017 (2) | 0.0003 (3) | −0.0003 (3) |
C10 | 0.0185 (3) | 0.0396 (4) | 0.0235 (3) | 0.0032 (3) | −0.0020 (2) | 0.0076 (3) |
C11 | 0.0140 (2) | 0.0175 (3) | 0.0155 (2) | 0.0000 (2) | 0.00058 (19) | 0.00121 (19) |
C12 | 0.0195 (3) | 0.0183 (3) | 0.0199 (3) | −0.0009 (2) | −0.0012 (2) | 0.0025 (2) |
C13 | 0.0243 (3) | 0.0248 (3) | 0.0235 (3) | 0.0001 (3) | −0.0014 (2) | 0.0078 (2) |
C14 | 0.0249 (3) | 0.0343 (4) | 0.0177 (3) | 0.0030 (3) | −0.0017 (2) | 0.0053 (3) |
C15 | 0.0228 (3) | 0.0299 (3) | 0.0169 (3) | 0.0027 (3) | −0.0019 (2) | −0.0024 (2) |
C16 | 0.0191 (3) | 0.0200 (3) | 0.0181 (3) | 0.0001 (2) | 0.0001 (2) | −0.0011 (2) |
C17 | 0.0157 (3) | 0.0247 (3) | 0.0151 (3) | 0.0034 (2) | −0.0002 (2) | 0.0011 (2) |
C18 | 0.0189 (3) | 0.0184 (3) | 0.0184 (3) | 0.0004 (2) | −0.0027 (2) | 0.0026 (2) |
C19 | 0.0210 (3) | 0.0351 (4) | 0.0333 (4) | 0.0090 (3) | 0.0043 (3) | 0.0111 (3) |
C20 | 0.0322 (4) | 0.0299 (4) | 0.0214 (3) | 0.0024 (3) | −0.0091 (3) | 0.0007 (3) |
C21 | 0.0422 (5) | 0.0208 (3) | 0.0332 (4) | −0.0059 (3) | −0.0137 (3) | 0.0053 (3) |
O1—C1 | 1.4422 (8) | C9—H92 | 0.980 |
O1—N | 1.4595 (7) | C9—H93 | 0.980 |
O2—C17 | 1.4158 (8) | C10—H101 | 1.000 |
O2—C18 | 1.4446 (8) | C10—H102 | 1.000 |
N—C6 | 1.4987 (9) | C10—H103 | 1.000 |
N—C2 | 1.5033 (9) | C11—C12 | 1.3945 (10) |
C1—C11 | 1.5168 (9) | C11—C16 | 1.3975 (9) |
C1—C17 | 1.5228 (9) | C12—C13 | 1.3955 (10) |
C1—H1 | 1.000 | C12—H12 | 0.950 |
C2—C8 | 1.5354 (11) | C13—C14 | 1.3883 (12) |
C2—C7 | 1.5377 (12) | C13—H13 | 0.950 |
C2—C3 | 1.5399 (11) | C14—C15 | 1.3906 (12) |
C3—C4 | 1.5198 (14) | C14—H14 | 0.950 |
C3—H31 | 0.990 | C15—C16 | 1.3924 (10) |
C3—H32 | 0.990 | C15—H15 | 0.950 |
C4—C5 | 1.5153 (13) | C16—H16 | 0.950 |
C4—H41 | 0.990 | C17—H171 | 0.990 |
C4—H42 | 0.990 | C17—H172 | 0.990 |
C5—C6 | 1.5312 (10) | C18—C20 | 1.5187 (10) |
C5—H51 | 0.990 | C18—C21 | 1.5200 (11) |
C5—H52 | 0.990 | C18—C19 | 1.5238 (11) |
C6—C10 | 1.5280 (10) | C19—H191 | 1.000 |
C6—C9 | 1.5353 (11) | C19—H192 | 1.000 |
C7—H71 | 0.980 | C19—H193 | 1.000 |
C7—H72 | 0.980 | C20—H201 | 1.000 |
C7—H73 | 0.980 | C20—H202 | 1.000 |
C8—H81 | 0.990 | C20—H203 | 1.000 |
C8—H82 | 0.990 | C21—H211 | 0.990 |
C8—H83 | 0.990 | C21—H212 | 0.990 |
C9—H91 | 0.980 | C21—H213 | 0.990 |
C1—O1—N | 112.33 (5) | H91—C9—H93 | 109.5 |
C17—O2—C18 | 116.92 (5) | H92—C9—H93 | 109.5 |
O1—N—C6 | 106.17 (5) | C6—C10—H101 | 109.5 |
O1—N—C2 | 107.19 (5) | C6—C10—H102 | 109.5 |
C6—N—C2 | 117.35 (5) | H101—C10—H102 | 109.5 |
O1—C1—C11 | 114.45 (5) | C6—C10—H103 | 109.5 |
O1—C1—C17 | 105.37 (5) | H101—C10—H103 | 109.5 |
C11—C1—C17 | 110.04 (5) | H102—C10—H103 | 109.5 |
O1—C1—H1 | 108.9 | C12—C11—C16 | 118.62 (6) |
C11—C1—H1 | 108.9 | C12—C11—C1 | 119.94 (6) |
C17—C1—H1 | 108.9 | C16—C11—C1 | 121.40 (6) |
N—C2—C8 | 108.10 (5) | C11—C12—C13 | 120.97 (7) |
N—C2—C7 | 114.93 (6) | C11—C12—H12 | 119.5 |
C8—C2—C7 | 107.59 (7) | C13—C12—H12 | 119.5 |
N—C2—C3 | 107.44 (6) | C14—C13—C12 | 119.75 (7) |
C8—C2—C3 | 106.83 (6) | C14—C13—H13 | 120.1 |
C7—C2—C3 | 111.61 (6) | C12—C13—H13 | 120.1 |
C4—C3—C2 | 114.33 (7) | C13—C14—C15 | 119.90 (7) |
C4—C3—H31 | 108.7 | C13—C14—H14 | 120.0 |
C2—C3—H31 | 108.7 | C15—C14—H14 | 120.1 |
C4—C3—H32 | 108.7 | C14—C15—C16 | 120.16 (7) |
C2—C3—H32 | 108.7 | C14—C15—H15 | 119.9 |
H31—C3—H32 | 107.6 | C16—C15—H15 | 119.9 |
C5—C4—C3 | 108.36 (7) | C15—C16—C11 | 120.59 (7) |
C5—C4—H41 | 110.0 | C15—C16—H16 | 119.7 |
C3—C4—H41 | 110.0 | C11—C16—H16 | 119.7 |
C5—C4—H42 | 110.0 | O2—C17—C1 | 108.48 (5) |
C3—C4—H42 | 110.0 | O2—C17—H171 | 110.0 |
H41—C4—H42 | 108.4 | C1—C17—H171 | 110.0 |
C4—C5—C6 | 112.78 (6) | O2—C17—H172 | 110.0 |
C4—C5—H51 | 109.0 | C1—C17—H172 | 110.0 |
C6—C5—H51 | 109.0 | H171—C17—H172 | 108.4 |
C4—C5—H52 | 109.1 | O2—C18—C20 | 103.38 (6) |
C6—C5—H52 | 109.0 | O2—C18—C21 | 111.07 (6) |
H51—C5—H52 | 107.8 | C20—C18—C21 | 110.35 (6) |
N—C6—C10 | 107.23 (5) | O2—C18—C19 | 111.02 (6) |
N—C6—C5 | 107.65 (6) | C20—C18—C19 | 110.12 (7) |
C10—C6—C5 | 107.62 (6) | C21—C18—C19 | 110.68 (7) |
N—C6—C9 | 116.15 (5) | C18—C19—H191 | 109.5 |
C10—C6—C9 | 107.67 (6) | C18—C19—H192 | 109.5 |
C5—C6—C9 | 110.19 (6) | H191—C19—H192 | 109.5 |
C2—C7—H71 | 109.5 | C18—C19—H193 | 109.5 |
C2—C7—H72 | 109.5 | H191—C19—H193 | 109.5 |
H71—C7—H72 | 109.5 | H192—C19—H193 | 109.5 |
C2—C7—H73 | 109.5 | C18—C20—H201 | 109.5 |
H71—C7—H73 | 109.5 | C18—C20—H202 | 109.5 |
H72—C7—H73 | 109.5 | H201—C20—H202 | 109.5 |
C2—C8—H81 | 109.5 | C18—C20—H203 | 109.5 |
C2—C8—H82 | 109.5 | H201—C20—H203 | 109.5 |
H81—C8—H82 | 109.5 | H202—C20—H203 | 109.5 |
C2—C8—H83 | 109.5 | C18—C21—H211 | 109.5 |
H81—C8—H83 | 109.5 | C18—C21—H212 | 109.5 |
H82—C8—H83 | 109.5 | H211—C21—H212 | 109.5 |
C6—C9—H91 | 109.5 | C18—C21—H213 | 109.5 |
C6—C9—H92 | 109.5 | H211—C21—H213 | 109.5 |
H91—C9—H92 | 109.5 | H212—C21—H213 | 109.5 |
C6—C9—H93 | 109.5 | ||
C1—O1—N—C6 | −128.03 (5) | O1—N—C6—C5 | −174.94 (5) |
C1—O1—N—C2 | 105.78 (6) | C2—N—C6—C5 | −55.17 (7) |
N—O1—C1—C11 | 86.82 (6) | O1—N—C6—C9 | −50.91 (7) |
N—O1—C1—C17 | −152.16 (5) | C2—N—C6—C9 | 68.86 (8) |
O1—N—C2—C8 | −72.99 (7) | C4—C5—C6—N | 56.34 (8) |
C6—N—C2—C8 | 167.78 (6) | C4—C5—C6—C10 | 171.63 (7) |
O1—N—C2—C7 | 47.18 (7) | C4—C5—C6—C9 | −71.23 (8) |
C6—N—C2—C7 | −72.05 (8) | O1—C1—C11—C12 | −117.89 (6) |
O1—N—C2—C3 | 172.05 (5) | C17—C1—C11—C12 | 123.70 (7) |
C6—N—C2—C3 | 52.82 (8) | O1—C1—C11—C16 | 64.45 (8) |
N—C2—C3—C4 | −52.39 (9) | C17—C1—C11—C16 | −53.96 (8) |
C8—C2—C3—C4 | −168.19 (7) | C18—O2—C17—C1 | −179.32 (5) |
C7—C2—C3—C4 | 74.46 (9) | O1—C1—C17—O2 | 72.26 (6) |
C2—C3—C4—C5 | 56.39 (10) | C11—C1—C17—O2 | −163.88 (5) |
C3—C4—C5—C6 | −57.99 (9) | C17—O2—C18—C20 | −173.50 (6) |
O1—N—C6—C10 | 69.52 (6) | C17—O2—C18—C21 | 68.17 (8) |
C2—N—C6—C10 | −170.72 (6) | C17—O2—C18—C19 | −55.45 (8) |
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