Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015303/hk2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015303/hk2032Isup2.hkl |
CCDC reference: 603120
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C31H27NO2 | F(000) = 944 |
Mr = 445.54 | Dx = 1.307 Mg m−3 |
Monoclinic, P21/n | Melting point = 480–482 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71070 Å |
a = 14.783 (2) Å | Cell parameters from 7710 reflections |
b = 9.4408 (12) Å | θ = 3.0–25.3° |
c = 16.345 (2) Å | µ = 0.08 mm−1 |
β = 96.878 (3)° | T = 173 K |
V = 2264.6 (5) Å3 | Block, red |
Z = 4 | 0.79 × 0.32 × 0.14 mm |
Rigaku Mercury diffractometer | 4144 independent reflections |
Radiation source: fine-focus sealed tube | 3611 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.4°, θmin = 3.3° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.939, Tmax = 0.989 | l = −19→19 |
21579 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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0325P)2 + 0.9725P] where P = (Fo2 + 2Fc2)/3 |
4144 reflections | (Δ/σ)max < 0.001 |
310 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Experimental. 1H NMR (DMSO-d6, δ, p.p.m.): 7.52–7.61 (m, 4H, ArH), 7.34 (d, 1H, ArH, J = 6.8 Hz), 7.18–7.26 (m, 4H, ArH), 6.94 (t, 1H, ArH, J = 7.6 Hz), 6.89 (d, 2H, ArH, J = 6.8 Hz), 6.21 (s, 1H, ArH), 4.91 (d, 1H, ArH, J = 7.6 Hz), 4.20 (t, 1H, CH, J = 3.8 Hz), 2.78–2.87 (m, 2H, CH2), 2.28 (s, 2H, CH2), 2.16 (d, 1H, CH2, J = 17.6 Hz), 1.63 (d, 1H, CH2, J = 17.6 Hz), 0.93 (s, 3H, CH3), 0.91(s, 3H, CH3). |
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 | 1.07434 (10) | 0.80923 (16) | 0.54032 (9) | 0.0447 (4) | |
O2 | 0.79919 (10) | 0.74458 (14) | 0.73821 (8) | 0.0396 (4) | |
N1 | 0.79564 (10) | 0.56606 (16) | 0.46614 (9) | 0.0268 (4) | |
C1 | 0.88118 (12) | 0.62213 (19) | 0.46130 (11) | 0.0265 (4) | |
C2 | 0.92401 (12) | 0.7058 (2) | 0.52096 (12) | 0.0287 (4) | |
C3 | 0.88337 (13) | 0.75617 (19) | 0.59465 (12) | 0.0287 (4) | |
H3 | 0.9280 | 0.7352 | 0.6441 | 0.034* | |
C4 | 0.79891 (12) | 0.66795 (19) | 0.60181 (11) | 0.0261 (4) | |
C5 | 0.75762 (12) | 0.58513 (19) | 0.54035 (11) | 0.0249 (4) | |
C6 | 1.01483 (13) | 0.7402 (2) | 0.49968 (13) | 0.0332 (5) | |
C7 | 1.02140 (13) | 0.6719 (2) | 0.41787 (12) | 0.0322 (5) | |
C8 | 1.09108 (14) | 0.6730 (2) | 0.36971 (14) | 0.0391 (5) | |
H8 | 1.1451 | 0.7256 | 0.3857 | 0.047* | |
C9 | 1.08106 (14) | 0.5954 (2) | 0.29670 (14) | 0.0410 (5) | |
H9 | 1.1280 | 0.5967 | 0.2618 | 0.049* | |
C10 | 1.00340 (14) | 0.5168 (2) | 0.27496 (13) | 0.0390 (5) | |
H10 | 0.9984 | 0.4622 | 0.2258 | 0.047* | |
C11 | 0.93145 (14) | 0.5157 (2) | 0.32393 (12) | 0.0339 (5) | |
H11 | 0.8781 | 0.4613 | 0.3084 | 0.041* | |
C12 | 0.94043 (13) | 0.5955 (2) | 0.39501 (12) | 0.0294 (4) | |
C13 | 0.76267 (13) | 0.67117 (19) | 0.68133 (11) | 0.0288 (4) | |
C14 | 0.68374 (13) | 0.5779 (2) | 0.69386 (11) | 0.0285 (4) | |
H14A | 0.6502 | 0.6207 | 0.7366 | 0.034* | |
H14B | 0.7073 | 0.4850 | 0.7148 | 0.034* | |
C15 | 0.61742 (12) | 0.55395 (19) | 0.61619 (11) | 0.0275 (4) | |
C16 | 0.67250 (12) | 0.5017 (2) | 0.54825 (11) | 0.0272 (4) | |
H16A | 0.6895 | 0.4015 | 0.5594 | 0.033* | |
H16B | 0.6330 | 0.5049 | 0.4949 | 0.033* | |
C17 | 0.56774 (14) | 0.6921 (2) | 0.59078 (13) | 0.0380 (5) | |
H17A | 0.5365 | 0.7268 | 0.6364 | 0.057* | |
H17B | 0.5230 | 0.6750 | 0.5425 | 0.057* | |
H17C | 0.6119 | 0.7631 | 0.5771 | 0.057* | |
C18 | 0.54838 (13) | 0.4415 (2) | 0.63422 (12) | 0.0354 (5) | |
H18A | 0.5805 | 0.3543 | 0.6527 | 0.053* | |
H18B | 0.5069 | 0.4222 | 0.5841 | 0.053* | |
H18C | 0.5133 | 0.4758 | 0.6775 | 0.053* | |
C19 | 0.74301 (12) | 0.5104 (2) | 0.39283 (11) | 0.0271 (4) | |
C20 | 0.72866 (13) | 0.3666 (2) | 0.38307 (12) | 0.0330 (5) | |
H20 | 0.7523 | 0.3019 | 0.4248 | 0.040* | |
C21 | 0.67891 (14) | 0.3184 (2) | 0.31098 (13) | 0.0387 (5) | |
H21 | 0.6675 | 0.2198 | 0.3040 | 0.046* | |
C22 | 0.64589 (14) | 0.4108 (2) | 0.24959 (12) | 0.0381 (5) | |
H22 | 0.6122 | 0.3759 | 0.2006 | 0.046* | |
C23 | 0.66172 (13) | 0.5544 (2) | 0.25904 (12) | 0.0370 (5) | |
H23 | 0.6398 | 0.6185 | 0.2164 | 0.044* | |
C24 | 0.70992 (13) | 0.6043 (2) | 0.33137 (11) | 0.0314 (4) | |
H24 | 0.7202 | 0.7031 | 0.3387 | 0.038* | |
C25 | 0.86565 (13) | 0.9194 (2) | 0.59340 (12) | 0.0324 (5) | |
H25A | 0.8650 | 0.9523 | 0.6508 | 0.039* | |
H25B | 0.9171 | 0.9670 | 0.5712 | 0.039* | |
C26 | 0.77827 (13) | 0.96529 (19) | 0.54351 (12) | 0.0297 (4) | |
C27 | 0.76343 (15) | 0.9440 (2) | 0.45905 (12) | 0.0375 (5) | |
H27 | 0.8102 | 0.9030 | 0.4316 | 0.045* | |
C28 | 0.68174 (16) | 0.9813 (2) | 0.41408 (14) | 0.0450 (6) | |
H28 | 0.6722 | 0.9635 | 0.3565 | 0.054* | |
C29 | 0.61387 (15) | 1.0444 (2) | 0.45278 (14) | 0.0435 (5) | |
H29 | 0.5575 | 1.0693 | 0.4221 | 0.052* | |
C30 | 0.62869 (15) | 1.0707 (2) | 0.53576 (14) | 0.0410 (5) | |
H30 | 0.5831 | 1.1166 | 0.5624 | 0.049* | |
C31 | 0.70966 (15) | 1.0306 (2) | 0.58081 (13) | 0.0370 (5) | |
H31 | 0.7186 | 1.0480 | 0.6385 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0331 (8) | 0.0468 (9) | 0.0527 (10) | −0.0118 (7) | −0.0008 (7) | 0.0021 (7) |
O2 | 0.0499 (9) | 0.0392 (8) | 0.0289 (8) | −0.0091 (7) | 0.0015 (7) | −0.0048 (6) |
N1 | 0.0246 (8) | 0.0318 (9) | 0.0238 (8) | −0.0034 (7) | 0.0017 (6) | −0.0015 (6) |
C1 | 0.0227 (9) | 0.0249 (9) | 0.0314 (10) | 0.0017 (8) | 0.0013 (8) | 0.0071 (8) |
C2 | 0.0258 (10) | 0.0275 (10) | 0.0321 (11) | −0.0010 (8) | 0.0007 (8) | 0.0051 (8) |
C3 | 0.0286 (10) | 0.0294 (10) | 0.0269 (10) | −0.0036 (8) | −0.0019 (8) | 0.0027 (8) |
C4 | 0.0252 (9) | 0.0247 (9) | 0.0276 (10) | 0.0007 (8) | −0.0001 (8) | 0.0044 (8) |
C5 | 0.0247 (9) | 0.0257 (9) | 0.0237 (9) | 0.0025 (8) | 0.0004 (7) | 0.0038 (7) |
C6 | 0.0298 (11) | 0.0281 (10) | 0.0406 (12) | −0.0008 (9) | −0.0005 (9) | 0.0098 (9) |
C7 | 0.0278 (10) | 0.0306 (10) | 0.0381 (11) | 0.0026 (9) | 0.0035 (8) | 0.0112 (9) |
C8 | 0.0288 (11) | 0.0395 (12) | 0.0499 (14) | 0.0028 (9) | 0.0085 (10) | 0.0146 (10) |
C9 | 0.0326 (11) | 0.0479 (13) | 0.0456 (13) | 0.0143 (10) | 0.0175 (10) | 0.0185 (10) |
C10 | 0.0381 (12) | 0.0464 (12) | 0.0338 (12) | 0.0131 (10) | 0.0094 (9) | 0.0073 (9) |
C11 | 0.0296 (10) | 0.0395 (11) | 0.0327 (11) | 0.0052 (9) | 0.0039 (9) | 0.0071 (9) |
C12 | 0.0278 (10) | 0.0297 (10) | 0.0310 (11) | 0.0049 (8) | 0.0045 (8) | 0.0096 (8) |
C13 | 0.0338 (10) | 0.0260 (10) | 0.0253 (10) | 0.0018 (8) | −0.0017 (8) | 0.0011 (8) |
C14 | 0.0315 (10) | 0.0315 (10) | 0.0228 (10) | 0.0009 (8) | 0.0037 (8) | 0.0018 (8) |
C15 | 0.0262 (10) | 0.0301 (10) | 0.0265 (10) | 0.0015 (8) | 0.0044 (8) | 0.0018 (8) |
C16 | 0.0244 (10) | 0.0303 (10) | 0.0266 (10) | −0.0008 (8) | 0.0017 (8) | −0.0009 (8) |
C17 | 0.0350 (11) | 0.0403 (12) | 0.0379 (12) | 0.0079 (10) | 0.0012 (9) | −0.0010 (9) |
C18 | 0.0288 (10) | 0.0433 (12) | 0.0347 (11) | −0.0034 (9) | 0.0058 (9) | 0.0009 (9) |
C19 | 0.0230 (9) | 0.0339 (10) | 0.0248 (10) | −0.0020 (8) | 0.0047 (8) | −0.0032 (8) |
C20 | 0.0354 (11) | 0.0330 (11) | 0.0319 (11) | −0.0021 (9) | 0.0088 (9) | −0.0016 (8) |
C21 | 0.0427 (12) | 0.0369 (12) | 0.0383 (12) | −0.0095 (10) | 0.0125 (10) | −0.0120 (9) |
C22 | 0.0339 (11) | 0.0531 (14) | 0.0276 (11) | −0.0082 (10) | 0.0044 (9) | −0.0119 (10) |
C23 | 0.0332 (11) | 0.0499 (13) | 0.0274 (11) | 0.0006 (10) | 0.0021 (9) | 0.0024 (9) |
C24 | 0.0316 (11) | 0.0333 (11) | 0.0294 (10) | −0.0005 (9) | 0.0036 (8) | 0.0001 (8) |
C25 | 0.0352 (11) | 0.0296 (10) | 0.0322 (11) | −0.0056 (9) | 0.0032 (9) | −0.0027 (8) |
C26 | 0.0377 (11) | 0.0210 (9) | 0.0309 (11) | −0.0043 (8) | 0.0063 (9) | 0.0014 (8) |
C27 | 0.0483 (13) | 0.0327 (11) | 0.0317 (11) | 0.0094 (10) | 0.0060 (10) | 0.0018 (9) |
C28 | 0.0624 (15) | 0.0361 (12) | 0.0338 (12) | 0.0125 (11) | −0.0048 (11) | −0.0012 (9) |
C29 | 0.0432 (13) | 0.0326 (12) | 0.0521 (14) | 0.0069 (10) | −0.0047 (11) | 0.0021 (10) |
C30 | 0.0426 (13) | 0.0316 (11) | 0.0505 (14) | 0.0049 (10) | 0.0127 (11) | 0.0009 (10) |
C31 | 0.0465 (13) | 0.0316 (11) | 0.0333 (11) | −0.0020 (10) | 0.0066 (10) | 0.0002 (9) |
O1—C6 | 1.224 (2) | C16—H16A | 0.9900 |
O2—C13 | 1.231 (2) | C16—H16B | 0.9900 |
N1—C1 | 1.382 (2) | C17—H17A | 0.9800 |
N1—C5 | 1.408 (2) | C17—H17B | 0.9800 |
N1—C19 | 1.447 (2) | C17—H17C | 0.9800 |
C1—C2 | 1.352 (3) | C18—H18A | 0.9800 |
C1—C12 | 1.494 (3) | C18—H18B | 0.9800 |
C2—C6 | 1.463 (3) | C18—H18C | 0.9800 |
C2—C3 | 1.487 (3) | C19—C20 | 1.381 (3) |
C3—C4 | 1.517 (3) | C19—C24 | 1.385 (3) |
C3—C25 | 1.562 (3) | C20—C21 | 1.389 (3) |
C3—H3 | 1.0000 | C20—H20 | 0.9500 |
C4—C5 | 1.359 (3) | C21—C22 | 1.374 (3) |
C4—C13 | 1.464 (3) | C21—H21 | 0.9500 |
C5—C16 | 1.503 (3) | C22—C23 | 1.382 (3) |
C6—C7 | 1.498 (3) | C22—H22 | 0.9500 |
C7—C8 | 1.369 (3) | C23—C24 | 1.388 (3) |
C7—C12 | 1.409 (3) | C23—H23 | 0.9500 |
C8—C9 | 1.393 (3) | C24—H24 | 0.9500 |
C8—H8 | 0.9500 | C25—C26 | 1.506 (3) |
C9—C10 | 1.377 (3) | C25—H25A | 0.9900 |
C9—H9 | 0.9500 | C25—H25B | 0.9900 |
C10—C11 | 1.406 (3) | C26—C27 | 1.386 (3) |
C10—H10 | 0.9500 | C26—C31 | 1.389 (3) |
C11—C12 | 1.378 (3) | C27—C28 | 1.382 (3) |
C11—H11 | 0.9500 | C27—H27 | 0.9500 |
C13—C14 | 1.495 (3) | C28—C29 | 1.383 (3) |
C14—C15 | 1.525 (2) | C28—H28 | 0.9500 |
C14—H14A | 0.9900 | C29—C30 | 1.370 (3) |
C14—H14B | 0.9900 | C29—H29 | 0.9500 |
C15—C18 | 1.525 (3) | C30—C31 | 1.381 (3) |
C15—C17 | 1.530 (3) | C30—H30 | 0.9500 |
C15—C16 | 1.535 (3) | C31—H31 | 0.9500 |
C1—N1—C5 | 117.56 (15) | C15—C16—H16A | 108.6 |
C1—N1—C19 | 119.78 (15) | C5—C16—H16B | 108.6 |
C5—N1—C19 | 121.95 (14) | C15—C16—H16B | 108.6 |
C2—C1—N1 | 122.36 (17) | H16A—C16—H16B | 107.6 |
C2—C1—C12 | 110.91 (16) | C15—C17—H17A | 109.5 |
N1—C1—C12 | 126.65 (16) | C15—C17—H17B | 109.5 |
C1—C2—C6 | 108.80 (17) | H17A—C17—H17B | 109.5 |
C1—C2—C3 | 124.85 (17) | C15—C17—H17C | 109.5 |
C6—C2—C3 | 126.33 (17) | H17A—C17—H17C | 109.5 |
C2—C3—C4 | 107.63 (15) | H17B—C17—H17C | 109.5 |
C2—C3—C25 | 112.85 (16) | C15—C18—H18A | 109.5 |
C4—C3—C25 | 113.84 (16) | C15—C18—H18B | 109.5 |
C2—C3—H3 | 107.4 | H18A—C18—H18B | 109.5 |
C4—C3—H3 | 107.4 | C15—C18—H18C | 109.5 |
C25—C3—H3 | 107.4 | H18A—C18—H18C | 109.5 |
C5—C4—C13 | 119.24 (17) | H18B—C18—H18C | 109.5 |
C5—C4—C3 | 124.05 (17) | C20—C19—C24 | 120.66 (18) |
C13—C4—C3 | 116.69 (16) | C20—C19—N1 | 120.85 (17) |
C4—C5—N1 | 121.34 (16) | C24—C19—N1 | 118.45 (17) |
C4—C5—C16 | 123.00 (17) | C19—C20—C21 | 118.61 (19) |
N1—C5—C16 | 115.57 (15) | C19—C20—H20 | 120.7 |
O1—C6—C2 | 127.5 (2) | C21—C20—H20 | 120.7 |
O1—C6—C7 | 126.45 (19) | C22—C21—C20 | 121.13 (19) |
C2—C6—C7 | 106.00 (16) | C22—C21—H21 | 119.4 |
C8—C7—C12 | 121.7 (2) | C20—C21—H21 | 119.4 |
C8—C7—C6 | 130.04 (19) | C21—C22—C23 | 120.07 (19) |
C12—C7—C6 | 108.27 (17) | C21—C22—H22 | 120.0 |
C7—C8—C9 | 118.6 (2) | C23—C22—H22 | 120.0 |
C7—C8—H8 | 120.7 | C22—C23—C24 | 119.42 (19) |
C9—C8—H8 | 120.7 | C22—C23—H23 | 120.3 |
C10—C9—C8 | 120.28 (19) | C24—C23—H23 | 120.3 |
C10—C9—H9 | 119.9 | C19—C24—C23 | 120.09 (19) |
C8—C9—H9 | 119.9 | C19—C24—H24 | 120.0 |
C9—C10—C11 | 121.4 (2) | C23—C24—H24 | 120.0 |
C9—C10—H10 | 119.3 | C26—C25—C3 | 114.99 (15) |
C11—C10—H10 | 119.3 | C26—C25—H25A | 108.5 |
C12—C11—C10 | 118.2 (2) | C3—C25—H25A | 108.5 |
C12—C11—H11 | 120.9 | C26—C25—H25B | 108.5 |
C10—C11—H11 | 120.9 | C3—C25—H25B | 108.5 |
C11—C12—C7 | 119.78 (18) | H25A—C25—H25B | 107.5 |
C11—C12—C1 | 134.27 (18) | C27—C26—C31 | 117.69 (19) |
C7—C12—C1 | 105.93 (16) | C27—C26—C25 | 121.36 (18) |
O2—C13—C4 | 120.53 (17) | C31—C26—C25 | 120.94 (18) |
O2—C13—C14 | 120.46 (17) | C28—C27—C26 | 121.1 (2) |
C4—C13—C14 | 118.94 (16) | C28—C27—H27 | 119.4 |
C13—C14—C15 | 114.06 (15) | C26—C27—H27 | 119.4 |
C13—C14—H14A | 108.7 | C27—C28—C29 | 120.1 (2) |
C15—C14—H14A | 108.7 | C27—C28—H28 | 119.9 |
C13—C14—H14B | 108.7 | C29—C28—H28 | 119.9 |
C15—C14—H14B | 108.7 | C30—C29—C28 | 119.5 (2) |
H14A—C14—H14B | 107.6 | C30—C29—H29 | 120.3 |
C14—C15—C18 | 108.71 (15) | C28—C29—H29 | 120.3 |
C14—C15—C17 | 109.84 (16) | C29—C30—C31 | 120.3 (2) |
C18—C15—C17 | 109.59 (16) | C29—C30—H30 | 119.9 |
C14—C15—C16 | 107.82 (15) | C31—C30—H30 | 119.9 |
C18—C15—C16 | 109.95 (15) | C30—C31—C26 | 121.3 (2) |
C17—C15—C16 | 110.90 (16) | C30—C31—H31 | 119.3 |
C5—C16—C15 | 114.56 (15) | C26—C31—H31 | 119.3 |
C5—C16—H16A | 108.6 | ||
C5—N1—C1—C2 | −7.2 (2) | C2—C1—C12—C11 | 177.2 (2) |
C19—N1—C1—C2 | 163.38 (17) | N1—C1—C12—C11 | 0.2 (3) |
C5—N1—C1—C12 | 169.48 (16) | C2—C1—C12—C7 | −1.4 (2) |
C19—N1—C1—C12 | −20.0 (3) | N1—C1—C12—C7 | −178.38 (16) |
N1—C1—C2—C6 | 176.65 (16) | C5—C4—C13—O2 | 179.50 (17) |
C12—C1—C2—C6 | −0.5 (2) | C3—C4—C13—O2 | 1.2 (3) |
N1—C1—C2—C3 | −4.7 (3) | C5—C4—C13—C14 | 2.8 (3) |
C12—C1—C2—C3 | 178.16 (16) | C3—C4—C13—C14 | −175.49 (16) |
C1—C2—C3—C4 | 14.6 (2) | O2—C13—C14—C15 | 150.56 (17) |
C6—C2—C3—C4 | −166.99 (17) | C4—C13—C14—C15 | −32.7 (2) |
C1—C2—C3—C25 | −111.8 (2) | C13—C14—C15—C18 | 172.02 (16) |
C6—C2—C3—C25 | 66.6 (2) | C13—C14—C15—C17 | −68.1 (2) |
C2—C3—C4—C5 | −14.9 (2) | C13—C14—C15—C16 | 52.9 (2) |
C25—C3—C4—C5 | 111.0 (2) | C4—C5—C16—C15 | 20.2 (2) |
C2—C3—C4—C13 | 163.35 (15) | N1—C5—C16—C15 | −163.31 (15) |
C25—C3—C4—C13 | −70.8 (2) | C14—C15—C16—C5 | −46.6 (2) |
C13—C4—C5—N1 | −172.81 (16) | C18—C15—C16—C5 | −164.98 (15) |
C3—C4—C5—N1 | 5.4 (3) | C17—C15—C16—C5 | 73.7 (2) |
C13—C4—C5—C16 | 3.5 (3) | C1—N1—C19—C20 | 109.2 (2) |
C3—C4—C5—C16 | −178.33 (16) | C5—N1—C19—C20 | −80.7 (2) |
C1—N1—C5—C4 | 6.7 (2) | C1—N1—C19—C24 | −68.7 (2) |
C19—N1—C5—C4 | −163.63 (17) | C5—N1—C19—C24 | 101.5 (2) |
C1—N1—C5—C16 | −169.84 (15) | C24—C19—C20—C21 | −1.2 (3) |
C19—N1—C5—C16 | 19.8 (2) | N1—C19—C20—C21 | −178.97 (17) |
C1—C2—C6—O1 | −177.12 (19) | C19—C20—C21—C22 | 1.3 (3) |
C3—C2—C6—O1 | 4.3 (3) | C20—C21—C22—C23 | −0.2 (3) |
C1—C2—C6—C7 | 2.1 (2) | C21—C22—C23—C24 | −1.0 (3) |
C3—C2—C6—C7 | −176.55 (17) | C20—C19—C24—C23 | 0.0 (3) |
O1—C6—C7—C8 | −2.0 (3) | N1—C19—C24—C23 | 177.89 (17) |
C2—C6—C7—C8 | 178.8 (2) | C22—C23—C24—C19 | 1.0 (3) |
O1—C6—C7—C12 | 176.25 (18) | C2—C3—C25—C26 | 82.6 (2) |
C2—C6—C7—C12 | −2.9 (2) | C4—C3—C25—C26 | −40.4 (2) |
C12—C7—C8—C9 | −0.5 (3) | C3—C25—C26—C27 | −63.6 (2) |
C6—C7—C8—C9 | 177.59 (19) | C3—C25—C26—C31 | 116.3 (2) |
C7—C8—C9—C10 | −1.5 (3) | C31—C26—C27—C28 | −2.5 (3) |
C8—C9—C10—C11 | 1.9 (3) | C25—C26—C27—C28 | 177.43 (19) |
C9—C10—C11—C12 | −0.1 (3) | C26—C27—C28—C29 | 1.7 (3) |
C10—C11—C12—C7 | −1.9 (3) | C27—C28—C29—C30 | 0.6 (3) |
C10—C11—C12—C1 | 179.68 (19) | C28—C29—C30—C31 | −1.9 (3) |
C8—C7—C12—C11 | 2.2 (3) | C29—C30—C31—C26 | 1.1 (3) |
C6—C7—C12—C11 | −176.24 (17) | C27—C26—C31—C30 | 1.2 (3) |
C8—C7—C12—C1 | −178.95 (17) | C25—C26—C31—C30 | −178.80 (18) |
C6—C7—C12—C1 | 2.62 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14B···O2i | 0.99 | 2.40 | 3.337 (2) | 157 |
C18—H18A···O2i | 0.98 | 2.58 | 3.429 (2) | 145 |
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2. |