Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024494/wn2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024494/wn2041IIsup2.hkl |
CCDC reference: 613845
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
C29H27NO5 | Dx = 1.139 Mg m−3 |
Mr = 469.52 | Melting point: 387 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
a = 13.373 (5) Å | Cell parameters from 2871 reflections |
b = 5.7653 (18) Å | θ = 1.5–27.9° |
c = 17.964 (6) Å | µ = 0.08 mm−1 |
β = 98.653 (5)° | T = 113 K |
V = 1369.2 (8) Å3 | Block, colourless |
Z = 2 | 0.32 × 0.22 × 0.20 mm |
F(000) = 496 |
Rigaku Saturn diffractometer | 3555 independent reflections |
Radiation source: rotating anode | 2777 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.038 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 1.8° |
ω scans | h = −16→17 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −7→5 |
Tmin = 0.976, Tmax = 0.985 | l = −23→19 |
8139 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0496P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.002 |
3555 reflections | Δρmax = 0.23 e Å−3 |
318 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (2) |
Experimental. Spectroscopic analysis: IR (KBr)ν(cm-1): 3039, 2903, 2859, 1650, 1604, 1457, 1403, 1345, 1148, 1130, 985, 763, 699. 1H NMR (CDCl3) δ (p.p.m.): 4.05 (dd, J = 12.74, 1.92 Hz, 1 H), 4.20 (dd, J = 13.32, 2.25 Hz, 1 H), 4.22 (d, J = 2.72 Hz, 1 H),4.30 (brs, 1H), 4.52 (d, J = 2.43 Hz, 1 H), 4.55 (dd, J = 6.72, 2.42 Hz, 2 H), 4.78 (d, J = 13.12 Hz, 1 H), 5.40 (d. J = 13.06 Hz, 1 H), 5.54 (d, J = 12.24 Hz, 2 H), 6.58 (d, J = 15.60 Hz, 1 H), 7.25–7.54 (m, 15 H), 7.95 (d, J = 15.60 Hz, 1 H). 13 C NMR (CDCl3) δ (p.p.m.): 54.83, 56.22, 60.39, 64.63, 67.59, 77.63, 78.52, 99.72, 99.79, 120.86, 126.08, 126.19, 127.89, 128.31, 128.36, 128.86, 129.14, 129.38, 129.82, 135.01, 137.80, 141.74, 166.64. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.76013 (12) | 0.9782 (3) | 0.12816 (8) | 0.0278 (4) | |
O2 | 0.95453 (11) | 0.4884 (3) | 0.27652 (7) | 0.0235 (3) | |
O3 | 0.85037 (11) | 0.6014 (3) | 0.36194 (7) | 0.0224 (3) | |
O4 | 0.58638 (11) | 0.5278 (3) | 0.30359 (8) | 0.0240 (4) | |
O5 | 0.51449 (11) | 0.7814 (3) | 0.21073 (8) | 0.0265 (4) | |
N1 | 0.74182 (14) | 0.6789 (3) | 0.20666 (9) | 0.0213 (4) | |
C1 | 0.77085 (17) | 0.4496 (4) | 0.23885 (11) | 0.0218 (5) | |
H1 | 0.7194 | 0.3325 | 0.2172 | 0.026* | |
C2 | 0.76273 (16) | 0.4864 (4) | 0.32267 (11) | 0.0210 (4) | |
H2 | 0.7483 | 0.3380 | 0.3479 | 0.025* | |
C3 | 0.67774 (16) | 0.6585 (4) | 0.32187 (11) | 0.0229 (5) | |
H3 | 0.6808 | 0.7399 | 0.3713 | 0.027* | |
C4 | 0.69494 (17) | 0.8254 (4) | 0.25901 (11) | 0.0222 (5) | |
H4 | 0.7445 | 0.9471 | 0.2802 | 0.027* | |
C5 | 0.87622 (16) | 0.3603 (4) | 0.23142 (11) | 0.0239 (5) | |
H5A | 0.8813 | 0.1951 | 0.2466 | 0.029* | |
H5B | 0.8862 | 0.3697 | 0.1780 | 0.029* | |
C6 | 0.94076 (16) | 0.4819 (4) | 0.35296 (10) | 0.0225 (5) | |
H6 | 0.9363 | 0.3171 | 0.3695 | 0.027* | |
C7 | 1.02936 (15) | 0.5989 (4) | 0.39972 (11) | 0.0216 (5) | |
C8 | 1.06573 (18) | 0.8098 (4) | 0.37722 (12) | 0.0267 (5) | |
H8 | 1.0329 | 0.8843 | 0.3330 | 0.032* | |
C9 | 1.14938 (18) | 0.9107 (4) | 0.41903 (12) | 0.0301 (6) | |
H9 | 1.1742 | 1.0543 | 0.4034 | 0.036* | |
C10 | 1.19750 (19) | 0.8033 (4) | 0.48387 (12) | 0.0317 (6) | |
H10 | 1.2552 | 0.8729 | 0.5126 | 0.038* | |
C11 | 1.16080 (18) | 0.5939 (5) | 0.50647 (12) | 0.0295 (5) | |
H11 | 1.1935 | 0.5201 | 0.5508 | 0.035* | |
C12 | 1.07648 (17) | 0.4913 (4) | 0.46457 (11) | 0.0245 (5) | |
H12 | 1.0513 | 0.3482 | 0.4803 | 0.029* | |
C13 | 0.50107 (16) | 0.6732 (4) | 0.27843 (12) | 0.0239 (5) | |
H13 | 0.4944 | 0.7936 | 0.3175 | 0.029* | |
C14 | 0.40939 (16) | 0.5211 (4) | 0.26804 (12) | 0.0247 (5) | |
C15 | 0.33177 (17) | 0.5623 (5) | 0.30982 (13) | 0.0333 (6) | |
H15 | 0.3352 | 0.6922 | 0.3426 | 0.040* | |
C16 | 0.24910 (18) | 0.4136 (5) | 0.30369 (15) | 0.0389 (7) | |
H16 | 0.1957 | 0.4438 | 0.3318 | 0.047* | |
C17 | 0.24417 (19) | 0.2223 (5) | 0.25706 (13) | 0.0358 (6) | |
H17 | 0.1888 | 0.1180 | 0.2545 | 0.043* | |
C18 | 0.32060 (19) | 0.1827 (5) | 0.21388 (13) | 0.0341 (6) | |
H18 | 0.3167 | 0.0532 | 0.1809 | 0.041* | |
C19 | 0.40245 (18) | 0.3327 (4) | 0.21916 (12) | 0.0302 (6) | |
H19 | 0.4541 | 0.3066 | 0.1892 | 0.036* | |
C20 | 0.59625 (17) | 0.9436 (4) | 0.22397 (13) | 0.0265 (5) | |
H20A | 0.5791 | 1.0672 | 0.2581 | 0.032* | |
H20B | 0.6059 | 1.0169 | 0.1757 | 0.032* | |
C21 | 0.76252 (17) | 0.7671 (4) | 0.14022 (12) | 0.0239 (5) | |
C22 | 0.78395 (16) | 0.5967 (4) | 0.08319 (10) | 0.0241 (5) | |
H22 | 0.7625 | 0.4404 | 0.0865 | 0.029* | |
C23 | 0.83327 (17) | 0.6603 (4) | 0.02693 (10) | 0.0245 (5) | |
H23 | 0.8540 | 0.8178 | 0.0259 | 0.029* | |
C24 | 0.85820 (17) | 0.5086 (4) | −0.03327 (11) | 0.0221 (5) | |
C25 | 0.80792 (18) | 0.2991 (4) | −0.05153 (11) | 0.0261 (5) | |
H25 | 0.7561 | 0.2508 | −0.0241 | 0.031* | |
C26 | 0.83263 (18) | 0.1618 (4) | −0.10884 (12) | 0.0293 (5) | |
H26 | 0.7964 | 0.0223 | −0.1217 | 0.035* | |
C27 | 0.91032 (19) | 0.2264 (5) | −0.14793 (12) | 0.0309 (6) | |
H27 | 0.9279 | 0.1302 | −0.1869 | 0.037* | |
C28 | 0.96191 (18) | 0.4317 (4) | −0.12981 (12) | 0.0292 (6) | |
H28 | 1.0157 | 0.4756 | −0.1559 | 0.035* | |
C29 | 0.93512 (17) | 0.5739 (4) | −0.07337 (11) | 0.0258 (5) | |
H29 | 0.9696 | 0.7167 | −0.0621 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0394 (10) | 0.0172 (9) | 0.0286 (8) | −0.0023 (7) | 0.0110 (7) | 0.0011 (7) |
O2 | 0.0225 (8) | 0.0281 (9) | 0.0213 (7) | −0.0029 (7) | 0.0074 (6) | −0.0025 (7) |
O3 | 0.0203 (8) | 0.0238 (9) | 0.0241 (7) | 0.0003 (7) | 0.0067 (6) | −0.0027 (6) |
O4 | 0.0198 (8) | 0.0235 (9) | 0.0297 (8) | −0.0027 (6) | 0.0067 (6) | −0.0024 (7) |
O5 | 0.0237 (8) | 0.0220 (9) | 0.0339 (8) | 0.0005 (7) | 0.0041 (7) | 0.0023 (7) |
N1 | 0.0257 (10) | 0.0173 (10) | 0.0225 (9) | 0.0019 (8) | 0.0088 (8) | −0.0010 (7) |
C1 | 0.0258 (12) | 0.0167 (12) | 0.0240 (10) | 0.0002 (9) | 0.0066 (9) | −0.0011 (9) |
C2 | 0.0223 (11) | 0.0181 (11) | 0.0233 (10) | −0.0043 (9) | 0.0060 (9) | −0.0014 (9) |
C3 | 0.0207 (11) | 0.0235 (12) | 0.0259 (10) | −0.0024 (9) | 0.0080 (9) | −0.0043 (9) |
C4 | 0.0237 (11) | 0.0179 (12) | 0.0271 (11) | −0.0017 (9) | 0.0103 (10) | −0.0025 (9) |
C5 | 0.0282 (12) | 0.0204 (12) | 0.0237 (10) | 0.0006 (10) | 0.0059 (9) | −0.0050 (9) |
C6 | 0.0238 (11) | 0.0220 (12) | 0.0234 (10) | −0.0004 (9) | 0.0094 (9) | −0.0006 (9) |
C7 | 0.0194 (11) | 0.0211 (12) | 0.0259 (10) | 0.0014 (9) | 0.0084 (9) | −0.0035 (9) |
C8 | 0.0320 (13) | 0.0231 (13) | 0.0256 (11) | 0.0016 (10) | 0.0059 (10) | 0.0010 (9) |
C9 | 0.0347 (14) | 0.0231 (13) | 0.0339 (13) | −0.0081 (10) | 0.0098 (11) | −0.0018 (10) |
C10 | 0.0295 (13) | 0.0356 (16) | 0.0304 (12) | −0.0037 (11) | 0.0060 (10) | −0.0069 (11) |
C11 | 0.0294 (12) | 0.0318 (13) | 0.0270 (11) | 0.0008 (11) | 0.0034 (10) | −0.0022 (10) |
C12 | 0.0281 (12) | 0.0232 (12) | 0.0237 (10) | −0.0002 (10) | 0.0086 (9) | −0.0008 (9) |
C13 | 0.0209 (12) | 0.0209 (12) | 0.0310 (11) | 0.0021 (9) | 0.0081 (9) | −0.0030 (9) |
C14 | 0.0214 (11) | 0.0215 (12) | 0.0312 (11) | 0.0021 (10) | 0.0037 (9) | −0.0002 (9) |
C15 | 0.0322 (13) | 0.0263 (14) | 0.0443 (13) | −0.0020 (11) | 0.0154 (11) | −0.0045 (11) |
C16 | 0.0271 (14) | 0.0393 (17) | 0.0532 (15) | −0.0031 (12) | 0.0154 (12) | 0.0047 (13) |
C17 | 0.0269 (13) | 0.0328 (16) | 0.0450 (14) | −0.0065 (11) | −0.0037 (11) | 0.0125 (12) |
C18 | 0.0348 (14) | 0.0257 (14) | 0.0379 (13) | 0.0006 (11) | −0.0067 (11) | 0.0000 (11) |
C19 | 0.0245 (12) | 0.0300 (15) | 0.0354 (13) | 0.0032 (10) | 0.0025 (10) | −0.0022 (10) |
C20 | 0.0268 (12) | 0.0180 (12) | 0.0363 (12) | 0.0008 (9) | 0.0100 (10) | 0.0007 (10) |
C21 | 0.0228 (12) | 0.0232 (13) | 0.0260 (11) | −0.0019 (10) | 0.0048 (9) | −0.0019 (9) |
C22 | 0.0305 (12) | 0.0189 (11) | 0.0233 (10) | −0.0021 (10) | 0.0055 (9) | −0.0015 (9) |
C23 | 0.0290 (13) | 0.0216 (12) | 0.0223 (10) | 0.0007 (10) | 0.0017 (9) | 0.0000 (9) |
C24 | 0.0275 (11) | 0.0195 (11) | 0.0187 (9) | 0.0009 (9) | 0.0019 (9) | 0.0032 (9) |
C25 | 0.0303 (13) | 0.0241 (13) | 0.0253 (11) | −0.0001 (10) | 0.0082 (10) | 0.0009 (9) |
C26 | 0.0346 (13) | 0.0243 (13) | 0.0293 (11) | −0.0010 (11) | 0.0056 (10) | −0.0045 (10) |
C27 | 0.0345 (14) | 0.0332 (15) | 0.0255 (11) | 0.0078 (11) | 0.0065 (10) | −0.0015 (10) |
C28 | 0.0286 (13) | 0.0314 (15) | 0.0299 (12) | 0.0029 (11) | 0.0118 (10) | 0.0055 (10) |
C29 | 0.0280 (12) | 0.0227 (12) | 0.0269 (11) | −0.0031 (10) | 0.0044 (10) | 0.0025 (9) |
O1—C21 | 1.236 (3) | C11—H11 | 0.9500 |
O2—C6 | 1.413 (2) | C12—H12 | 0.9500 |
O2—C5 | 1.429 (3) | C13—C14 | 1.496 (3) |
O3—C6 | 1.422 (2) | C13—H13 | 1.0000 |
O3—C2 | 1.436 (2) | C14—C15 | 1.390 (3) |
O4—C3 | 1.431 (3) | C14—C19 | 1.391 (3) |
O4—C13 | 1.433 (3) | C15—C16 | 1.390 (3) |
O5—C13 | 1.402 (3) | C15—H15 | 0.9500 |
O5—C20 | 1.431 (3) | C16—C17 | 1.381 (4) |
N1—C21 | 1.364 (3) | C16—H16 | 0.9500 |
N1—C1 | 1.471 (3) | C17—C18 | 1.392 (4) |
N1—C4 | 1.472 (3) | C17—H17 | 0.9500 |
C1—C5 | 1.525 (3) | C18—C19 | 1.387 (3) |
C1—C2 | 1.540 (3) | C18—H18 | 0.9500 |
C1—H1 | 1.0000 | C19—H19 | 0.9500 |
C2—C3 | 1.507 (3) | C20—H20A | 0.9900 |
C2—H2 | 1.0000 | C20—H20B | 0.9900 |
C3—C4 | 1.527 (3) | C21—C22 | 1.478 (3) |
C3—H3 | 1.0000 | C22—C23 | 1.339 (3) |
C4—C20 | 1.534 (3) | C22—H22 | 0.9500 |
C4—H4 | 1.0000 | C23—C24 | 1.468 (3) |
C5—H5A | 0.9900 | C23—H23 | 0.9500 |
C5—H5B | 0.9900 | C24—C29 | 1.393 (3) |
C6—C7 | 1.505 (3) | C24—C25 | 1.397 (3) |
C6—H6 | 1.0000 | C25—C26 | 1.377 (3) |
C7—C12 | 1.385 (3) | C25—H25 | 0.9500 |
C7—C8 | 1.392 (3) | C26—C27 | 1.390 (3) |
C8—C9 | 1.379 (3) | C26—H26 | 0.9500 |
C8—H8 | 0.9500 | C27—C28 | 1.384 (4) |
C9—C10 | 1.389 (3) | C27—H27 | 0.9500 |
C9—H9 | 0.9500 | C28—C29 | 1.392 (3) |
C10—C11 | 1.387 (4) | C28—H28 | 0.9500 |
C10—H10 | 0.9500 | C29—H29 | 0.9500 |
C11—C12 | 1.390 (3) | ||
C6—O2—C5 | 110.21 (16) | C7—C12—H12 | 120.2 |
C6—O3—C2 | 111.43 (16) | C11—C12—H12 | 120.2 |
C3—O4—C13 | 112.09 (17) | O5—C13—O4 | 109.51 (16) |
C13—O5—C20 | 109.93 (16) | O5—C13—C14 | 111.22 (18) |
C21—N1—C1 | 127.07 (18) | O4—C13—C14 | 107.16 (18) |
C21—N1—C4 | 120.47 (18) | O5—C13—H13 | 109.6 |
C1—N1—C4 | 112.14 (15) | O4—C13—H13 | 109.6 |
N1—C1—C5 | 117.50 (18) | C14—C13—H13 | 109.6 |
N1—C1—C2 | 101.96 (16) | C15—C14—C19 | 119.3 (2) |
C5—C1—C2 | 109.51 (17) | C15—C14—C13 | 119.8 (2) |
N1—C1—H1 | 109.2 | C19—C14—C13 | 120.80 (19) |
C5—C1—H1 | 109.2 | C14—C15—C16 | 120.1 (2) |
C2—C1—H1 | 109.2 | C14—C15—H15 | 119.9 |
O3—C2—C3 | 105.03 (17) | C16—C15—H15 | 119.9 |
O3—C2—C1 | 111.81 (16) | C17—C16—C15 | 120.4 (2) |
C3—C2—C1 | 104.20 (17) | C17—C16—H16 | 119.8 |
O3—C2—H2 | 111.8 | C15—C16—H16 | 119.8 |
C3—C2—H2 | 111.8 | C16—C17—C18 | 119.8 (2) |
C1—C2—H2 | 111.8 | C16—C17—H17 | 120.1 |
O4—C3—C2 | 105.80 (18) | C18—C17—H17 | 120.1 |
O4—C3—C4 | 112.36 (17) | C19—C18—C17 | 119.9 (2) |
C2—C3—C4 | 102.97 (16) | C19—C18—H18 | 120.1 |
O4—C3—H3 | 111.7 | C17—C18—H18 | 120.1 |
C2—C3—H3 | 111.7 | C18—C19—C14 | 120.5 (2) |
C4—C3—H3 | 111.7 | C18—C19—H19 | 119.8 |
N1—C4—C20 | 114.55 (17) | C14—C19—H19 | 119.8 |
N1—C4—C3 | 103.69 (17) | O5—C20—C4 | 111.51 (18) |
C20—C4—C3 | 111.55 (18) | O5—C20—H20A | 109.3 |
N1—C4—H4 | 108.9 | C4—C20—H20A | 109.3 |
C20—C4—H4 | 108.9 | O5—C20—H20B | 109.3 |
C3—C4—H4 | 108.9 | C4—C20—H20B | 109.3 |
O2—C5—C1 | 112.56 (17) | H20A—C20—H20B | 108.0 |
O2—C5—H5A | 109.1 | O1—C21—N1 | 121.2 (2) |
C1—C5—H5A | 109.1 | O1—C21—C22 | 122.39 (19) |
O2—C5—H5B | 109.1 | N1—C21—C22 | 116.4 (2) |
C1—C5—H5B | 109.1 | C23—C22—C21 | 120.7 (2) |
H5A—C5—H5B | 107.8 | C23—C22—H22 | 119.7 |
O2—C6—O3 | 109.55 (16) | C21—C22—H22 | 119.7 |
O2—C6—C7 | 108.88 (17) | C22—C23—C24 | 125.8 (2) |
O3—C6—C7 | 109.31 (18) | C22—C23—H23 | 117.1 |
O2—C6—H6 | 109.7 | C24—C23—H23 | 117.1 |
O3—C6—H6 | 109.7 | C29—C24—C25 | 118.6 (2) |
C7—C6—H6 | 109.7 | C29—C24—C23 | 119.2 (2) |
C12—C7—C8 | 120.1 (2) | C25—C24—C23 | 122.25 (19) |
C12—C7—C6 | 119.3 (2) | C26—C25—C24 | 120.7 (2) |
C8—C7—C6 | 120.7 (2) | C26—C25—H25 | 119.6 |
C9—C8—C7 | 120.0 (2) | C24—C25—H25 | 119.6 |
C9—C8—H8 | 120.0 | C25—C26—C27 | 120.4 (2) |
C7—C8—H8 | 120.0 | C25—C26—H26 | 119.8 |
C8—C9—C10 | 120.3 (2) | C27—C26—H26 | 119.8 |
C8—C9—H9 | 119.8 | C28—C27—C26 | 119.6 (2) |
C10—C9—H9 | 119.8 | C28—C27—H27 | 120.2 |
C11—C10—C9 | 119.6 (2) | C26—C27—H27 | 120.2 |
C11—C10—H10 | 120.2 | C27—C28—C29 | 120.1 (2) |
C9—C10—H10 | 120.2 | C27—C28—H28 | 120.0 |
C10—C11—C12 | 120.4 (2) | C29—C28—H28 | 120.0 |
C10—C11—H11 | 119.8 | C28—C29—C24 | 120.5 (2) |
C12—C11—H11 | 119.8 | C28—C29—H29 | 119.7 |
C7—C12—C11 | 119.6 (2) | C24—C29—H29 | 119.7 |
C21—N1—C1—C5 | 40.2 (3) | C8—C7—C12—C11 | −0.7 (3) |
C4—N1—C1—C5 | −133.30 (19) | C6—C7—C12—C11 | 177.48 (19) |
C21—N1—C1—C2 | 159.8 (2) | C10—C11—C12—C7 | 0.3 (3) |
C4—N1—C1—C2 | −13.6 (2) | C20—O5—C13—O4 | −67.7 (2) |
C6—O3—C2—C3 | −167.09 (15) | C20—O5—C13—C14 | 174.04 (17) |
C6—O3—C2—C1 | −54.7 (2) | C3—O4—C13—O5 | 64.4 (2) |
N1—C1—C2—O3 | −80.4 (2) | C3—O4—C13—C14 | −174.82 (15) |
C5—C1—C2—O3 | 44.7 (2) | O5—C13—C14—C15 | −120.9 (2) |
N1—C1—C2—C3 | 32.5 (2) | O4—C13—C14—C15 | 119.4 (2) |
C5—C1—C2—C3 | 157.65 (18) | O5—C13—C14—C19 | 61.6 (3) |
C13—O4—C3—C2 | −162.27 (15) | O4—C13—C14—C19 | −58.0 (3) |
C13—O4—C3—C4 | −50.6 (2) | C19—C14—C15—C16 | 1.2 (4) |
O3—C2—C3—O4 | −163.46 (14) | C13—C14—C15—C16 | −176.2 (2) |
C1—C2—C3—O4 | 78.85 (19) | C14—C15—C16—C17 | 1.0 (4) |
O3—C2—C3—C4 | 78.45 (19) | C15—C16—C17—C18 | −2.3 (4) |
C1—C2—C3—C4 | −39.2 (2) | C16—C17—C18—C19 | 1.4 (4) |
C21—N1—C4—C20 | 54.1 (3) | C17—C18—C19—C14 | 0.8 (4) |
C1—N1—C4—C20 | −131.99 (19) | C15—C14—C19—C18 | −2.1 (3) |
C21—N1—C4—C3 | 175.86 (18) | C13—C14—C19—C18 | 175.3 (2) |
C1—N1—C4—C3 | −10.2 (2) | C13—O5—C20—C4 | 58.0 (2) |
O4—C3—C4—N1 | −83.1 (2) | N1—C4—C20—O5 | 73.2 (2) |
C2—C3—C4—N1 | 30.3 (2) | C3—C4—C20—O5 | −44.2 (2) |
O4—C3—C4—C20 | 40.7 (2) | C1—N1—C21—O1 | −159.6 (2) |
C2—C3—C4—C20 | 154.06 (17) | C4—N1—C21—O1 | 13.3 (3) |
C6—O2—C5—C1 | 57.5 (2) | C1—N1—C21—C22 | 22.5 (3) |
N1—C1—C5—O2 | 69.2 (2) | C4—N1—C21—C22 | −164.49 (19) |
C2—C1—C5—O2 | −46.4 (2) | O1—C21—C22—C23 | 22.1 (3) |
C5—O2—C6—O3 | −65.7 (2) | N1—C21—C22—C23 | −160.1 (2) |
C5—O2—C6—C7 | 174.79 (18) | C21—C22—C23—C24 | −179.4 (2) |
C2—O3—C6—O2 | 65.0 (2) | C22—C23—C24—C29 | −160.0 (2) |
C2—O3—C6—C7 | −175.82 (16) | C22—C23—C24—C25 | 19.5 (3) |
O2—C6—C7—C12 | −132.9 (2) | C29—C24—C25—C26 | −1.1 (3) |
O3—C6—C7—C12 | 107.5 (2) | C23—C24—C25—C26 | 179.4 (2) |
O2—C6—C7—C8 | 45.3 (3) | C24—C25—C26—C27 | 2.0 (4) |
O3—C6—C7—C8 | −74.4 (2) | C25—C26—C27—C28 | −1.0 (4) |
C12—C7—C8—C9 | 0.7 (3) | C26—C27—C28—C29 | −0.8 (3) |
C6—C7—C8—C9 | −177.5 (2) | C27—C28—C29—C24 | 1.7 (3) |
C7—C8—C9—C10 | −0.3 (3) | C25—C24—C29—C28 | −0.7 (3) |
C8—C9—C10—C11 | −0.1 (3) | C23—C24—C29—C28 | 178.7 (2) |
C9—C10—C11—C12 | 0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20B···O1 | 0.99 | 2.36 | 2.990 (3) | 121 |
C27—H27···O2i | 0.95 | 2.55 | 3.427 (3) | 154 |
Symmetry code: (i) −x+2, y−1/2, −z. |