Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003703/lh6345sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003703/lh63453sup2.hkl |
CCDC reference: 269807
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.041
- wR factor = 0.089
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O1 .. C27B .. 2.91 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C23 - C24 ... 1.38 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C24 - C25 ... 1.36 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C28 PLAT432_ALERT_2_C Short Inter X...Y Contact C2 .. C2 .. 3.11 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) or SHELXS86 (Sheldrick, 1990)?; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C28H25N3O5 | Z = 2 |
Mr = 483.51 | F(000) = 508 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.901 (1) Å | Cell parameters from 14135 reflections |
b = 10.5060 (12) Å | θ = 2.0–28.8° |
c = 14.5942 (15) Å | µ = 0.09 mm−1 |
α = 92.522 (9)° | T = 296 K |
β = 104.923 (8)° | Prism, colorless |
γ = 106.330 (8)° | 0.29 × 0.20 × 0.07 mm |
V = 1255.5 (3) Å3 |
STOE IPDS-II diffractometer | 4430 independent reflections |
Radiation source: sealed X-ray tube | 2541 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.040 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −9→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.976, Tmax = 0.995 | l = −17→17 |
11921 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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4430 reflections | Δρmax = 0.17 e Å−3 |
345 parameters | Δρmin = −0.12 e Å−3 |
57 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0085 (10) |
Experimental. Solvents were dried by refluxing with the appropriate drying agent and distilled before use. Melting points were determined on the Electrothermal 9200 apparatus and are uncorrected. Microanalyses were performed on a Carlo Erba elemental analyser, Model 1108; the results agree favourably with the calculated values. The IR spectra were recorded on a Shimadzu Model 435 V-04 spectrometer, using potassium bromide discs. The 1H and 13C NMR spectra were recorded on a Gemini-Varian 200 instrument. The chemical shifts are reported in p.p.m. from tetramethylsilane and given in δ units. |
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 | Occ. (<1) | |
O1 | 0.30554 (18) | 0.93530 (14) | −0.07870 (9) | 0.0644 (4) | |
O2 | 0.4336 (2) | 0.91452 (14) | 0.35615 (9) | 0.0736 (5) | |
O3 | 1.1015 (2) | 1.38070 (19) | 0.48392 (11) | 0.0860 (5) | |
O4 | 0.42354 (19) | 1.59372 (14) | 0.31504 (10) | 0.0658 (4) | |
O5A | 0.0230 (15) | 0.1551 (10) | −0.2473 (7) | 0.102 (4) | 0.50 (3) |
O5B | 0.0082 (12) | 0.1517 (10) | −0.2452 (8) | 0.089 (4) | 0.50 (3) |
N1 | 0.3363 (2) | 1.06937 (16) | 0.05661 (10) | 0.0530 (4) | |
N2 | 0.3194 (2) | 0.84127 (15) | 0.05963 (10) | 0.0508 (4) | |
N3 | 0.2897 (2) | 0.71072 (16) | 0.01429 (11) | 0.0557 (4) | |
C1 | 0.3839 (2) | 1.08621 (19) | 0.15060 (12) | 0.0471 (5) | |
C2 | 0.3218 (2) | 0.9511 (2) | 0.00671 (13) | 0.0515 (5) | |
C3 | 0.3791 (2) | 0.8613 (2) | 0.15514 (13) | 0.0508 (5) | |
H3 | 0.3929 | 0.7896 | 0.1879 | 0.061* | |
C4 | 0.4195 (2) | 0.98360 (19) | 0.20487 (12) | 0.0469 (5) | |
C5 | 0.4972 (3) | 0.99744 (19) | 0.31053 (13) | 0.0516 (5) | |
C6 | 0.6533 (2) | 1.10181 (19) | 0.35537 (12) | 0.0473 (5) | |
C7 | 0.7161 (3) | 1.1195 (2) | 0.45427 (13) | 0.0586 (6) | |
H7 | 0.6560 | 1.0681 | 0.4905 | 0.070* | |
C8 | 0.8642 (3) | 1.2103 (2) | 0.49989 (14) | 0.0631 (6) | |
H8 | 0.9039 | 1.2205 | 0.5661 | 0.076* | |
C9 | 0.9536 (3) | 1.2865 (2) | 0.44647 (14) | 0.0615 (6) | |
C10 | 0.8940 (3) | 1.2702 (2) | 0.34786 (14) | 0.0629 (6) | |
H10 | 0.9551 | 1.3213 | 0.3120 | 0.075* | |
C11 | 0.7463 (3) | 1.1795 (2) | 0.30289 (13) | 0.0536 (5) | |
H11 | 0.7073 | 1.1696 | 0.2366 | 0.064* | |
C12 | 1.1663 (3) | 1.4071 (3) | 0.58554 (16) | 0.0982 (9) | |
H12A | 1.2700 | 1.4752 | 0.6018 | 0.147* | |
H12B | 1.1800 | 1.3268 | 0.6107 | 0.147* | |
H12C | 1.0924 | 1.4368 | 0.6124 | 0.147* | |
C13 | 0.3921 (2) | 1.21733 (19) | 0.19665 (13) | 0.0479 (5) | |
C14 | 0.3425 (3) | 1.2299 (2) | 0.27832 (13) | 0.0546 (5) | |
H14 | 0.3035 | 1.1537 | 0.3057 | 0.066* | |
C15 | 0.3498 (3) | 1.3531 (2) | 0.31995 (14) | 0.0558 (5) | |
H15 | 0.3152 | 1.3595 | 0.3744 | 0.067* | |
C16 | 0.4090 (2) | 1.4666 (2) | 0.27987 (13) | 0.0520 (5) | |
C17 | 0.4573 (3) | 1.4549 (2) | 0.19780 (14) | 0.0604 (6) | |
H17 | 0.4963 | 1.5310 | 0.1703 | 0.072* | |
C18 | 0.4480 (3) | 1.3324 (2) | 0.15677 (14) | 0.0563 (5) | |
H18 | 0.4798 | 1.3262 | 0.1012 | 0.068* | |
C19 | 0.3949 (4) | 1.6134 (2) | 0.40520 (16) | 0.0840 (8) | |
H19A | 0.4096 | 1.7065 | 0.4214 | 0.126* | |
H19B | 0.4704 | 1.5847 | 0.4531 | 0.126* | |
H19C | 0.2854 | 1.5623 | 0.4021 | 0.126* | |
C20 | 0.1477 (3) | 0.66005 (19) | −0.04623 (13) | 0.0495 (5) | |
C21 | 0.1167 (3) | 0.52614 (19) | −0.09597 (13) | 0.0500 (5) | |
C22 | 0.2273 (3) | 0.4545 (2) | −0.07239 (14) | 0.0599 (6) | |
H22 | 0.3237 | 0.4917 | −0.0238 | 0.072* | |
C23 | 0.1975 (3) | 0.3283 (2) | −0.11965 (15) | 0.0680 (6) | |
H23 | 0.2718 | 0.2807 | −0.1020 | 0.082* | |
C24 | 0.0560 (3) | 0.2746 (2) | −0.19317 (15) | 0.0622 (6) | |
C25 | −0.0553 (3) | 0.3427 (2) | −0.21729 (15) | 0.0632 (6) | |
H25 | −0.1513 | 0.3054 | −0.2661 | 0.076* | |
C26 | −0.0253 (3) | 0.4664 (2) | −0.16936 (14) | 0.0584 (5) | |
H26 | −0.1022 | 0.5118 | −0.1864 | 0.070* | |
C27A | 0.1439 (19) | 0.0948 (15) | −0.2491 (12) | 0.115 (4) | 0.50 (3) |
H27A | 0.0937 | 0.0044 | −0.2796 | 0.173* | 0.50 (3) |
H27B | 0.2070 | 0.0949 | −0.1849 | 0.173* | 0.50 (3) |
H27C | 0.2140 | 0.1438 | −0.2842 | 0.173* | 0.50 (3) |
C27B | 0.1012 (18) | 0.0633 (11) | −0.2071 (15) | 0.106 (5) | 0.50 (3) |
H27D | 0.0681 | −0.0162 | −0.2516 | 0.160* | 0.50 (3) |
H27E | 0.0817 | 0.0399 | −0.1475 | 0.160* | 0.50 (3) |
H27F | 0.2153 | 0.1077 | −0.1971 | 0.160* | 0.50 (3) |
C28 | 0.0152 (3) | 0.7245 (2) | −0.06781 (16) | 0.0661 (6) | |
H28A | 0.0523 | 0.8107 | −0.0305 | 0.099* | |
H28B | −0.0788 | 0.6694 | −0.0523 | 0.099* | |
H28C | −0.0133 | 0.7348 | −0.1345 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0810 (11) | 0.0726 (10) | 0.0346 (8) | 0.0162 (8) | 0.0158 (7) | 0.0026 (7) |
O2 | 0.0996 (13) | 0.0594 (9) | 0.0448 (8) | −0.0002 (9) | 0.0173 (8) | 0.0114 (7) |
O3 | 0.0622 (11) | 0.1141 (14) | 0.0576 (9) | −0.0020 (10) | 0.0103 (8) | −0.0068 (9) |
O4 | 0.0885 (12) | 0.0542 (9) | 0.0600 (9) | 0.0301 (8) | 0.0212 (8) | 0.0039 (7) |
O5A | 0.156 (8) | 0.063 (6) | 0.084 (6) | 0.034 (5) | 0.036 (5) | −0.024 (4) |
O5B | 0.069 (5) | 0.078 (6) | 0.098 (7) | 0.039 (4) | −0.028 (4) | −0.008 (4) |
N1 | 0.0625 (11) | 0.0555 (11) | 0.0379 (9) | 0.0167 (9) | 0.0105 (8) | 0.0055 (8) |
N2 | 0.0608 (11) | 0.0482 (10) | 0.0362 (8) | 0.0116 (8) | 0.0083 (8) | −0.0027 (8) |
N3 | 0.0646 (12) | 0.0518 (10) | 0.0431 (9) | 0.0124 (9) | 0.0095 (9) | −0.0038 (8) |
C1 | 0.0465 (12) | 0.0510 (12) | 0.0421 (11) | 0.0117 (10) | 0.0130 (9) | 0.0050 (9) |
C2 | 0.0502 (13) | 0.0583 (13) | 0.0401 (11) | 0.0110 (10) | 0.0087 (9) | 0.0043 (10) |
C3 | 0.0598 (13) | 0.0507 (12) | 0.0385 (10) | 0.0138 (10) | 0.0114 (9) | 0.0033 (9) |
C4 | 0.0545 (13) | 0.0457 (12) | 0.0372 (10) | 0.0115 (10) | 0.0117 (9) | 0.0041 (9) |
C5 | 0.0696 (15) | 0.0463 (12) | 0.0397 (10) | 0.0182 (11) | 0.0164 (10) | 0.0027 (9) |
C6 | 0.0601 (13) | 0.0483 (11) | 0.0333 (9) | 0.0181 (10) | 0.0116 (9) | 0.0010 (8) |
C7 | 0.0689 (15) | 0.0640 (14) | 0.0386 (11) | 0.0142 (12) | 0.0148 (10) | 0.0046 (10) |
C8 | 0.0669 (15) | 0.0780 (16) | 0.0356 (10) | 0.0159 (13) | 0.0077 (10) | −0.0008 (10) |
C9 | 0.0548 (14) | 0.0723 (15) | 0.0498 (12) | 0.0127 (12) | 0.0111 (11) | −0.0045 (11) |
C10 | 0.0629 (15) | 0.0782 (16) | 0.0428 (12) | 0.0114 (13) | 0.0188 (11) | 0.0032 (11) |
C11 | 0.0582 (14) | 0.0633 (13) | 0.0369 (10) | 0.0159 (12) | 0.0126 (10) | 0.0020 (10) |
C12 | 0.0755 (18) | 0.128 (2) | 0.0580 (15) | 0.0036 (17) | −0.0036 (13) | −0.0128 (15) |
C13 | 0.0515 (12) | 0.0499 (12) | 0.0422 (10) | 0.0168 (10) | 0.0112 (9) | 0.0056 (9) |
C14 | 0.0649 (14) | 0.0540 (13) | 0.0494 (11) | 0.0202 (11) | 0.0206 (10) | 0.0097 (10) |
C15 | 0.0635 (14) | 0.0623 (14) | 0.0474 (11) | 0.0258 (11) | 0.0179 (10) | 0.0080 (10) |
C16 | 0.0545 (13) | 0.0508 (13) | 0.0505 (11) | 0.0215 (10) | 0.0088 (10) | 0.0039 (10) |
C17 | 0.0737 (16) | 0.0528 (13) | 0.0565 (13) | 0.0174 (11) | 0.0229 (11) | 0.0104 (11) |
C18 | 0.0687 (15) | 0.0554 (13) | 0.0460 (11) | 0.0179 (11) | 0.0195 (10) | 0.0063 (10) |
C19 | 0.136 (2) | 0.0710 (16) | 0.0586 (14) | 0.0503 (16) | 0.0304 (15) | 0.0050 (12) |
C20 | 0.0519 (13) | 0.0536 (12) | 0.0407 (10) | 0.0099 (11) | 0.0160 (10) | 0.0042 (9) |
C21 | 0.0552 (13) | 0.0511 (12) | 0.0402 (10) | 0.0096 (11) | 0.0152 (9) | 0.0034 (9) |
C22 | 0.0594 (14) | 0.0611 (14) | 0.0510 (12) | 0.0144 (12) | 0.0066 (10) | 0.0024 (11) |
C23 | 0.0750 (17) | 0.0641 (15) | 0.0651 (14) | 0.0301 (13) | 0.0108 (12) | 0.0067 (12) |
C24 | 0.0766 (17) | 0.0535 (13) | 0.0504 (12) | 0.0161 (13) | 0.0126 (12) | −0.0022 (11) |
C25 | 0.0625 (15) | 0.0628 (14) | 0.0524 (12) | 0.0129 (12) | 0.0048 (11) | −0.0065 (11) |
C26 | 0.0590 (14) | 0.0602 (14) | 0.0500 (12) | 0.0167 (11) | 0.0079 (10) | −0.0008 (10) |
C27A | 0.179 (9) | 0.107 (7) | 0.088 (7) | 0.099 (7) | 0.024 (5) | 0.017 (4) |
C27B | 0.126 (8) | 0.077 (5) | 0.116 (9) | 0.058 (5) | 0.006 (6) | −0.002 (5) |
C28 | 0.0560 (14) | 0.0675 (15) | 0.0711 (14) | 0.0150 (12) | 0.0178 (11) | −0.0041 (12) |
O1—C2 | 1.216 (2) | C13—C18 | 1.386 (3) |
O2—C5 | 1.221 (2) | C13—C14 | 1.386 (2) |
O3—C9 | 1.364 (3) | C14—C15 | 1.383 (3) |
O3—C12 | 1.429 (3) | C14—H14 | 0.9300 |
O4—C16 | 1.368 (2) | C15—C16 | 1.381 (3) |
O4—C19 | 1.421 (2) | C15—H15 | 0.9300 |
O5A—C24 | 1.368 (8) | C16—C17 | 1.384 (3) |
O5A—C27A | 1.399 (10) | C17—C18 | 1.367 (3) |
O5B—C24 | 1.365 (8) | C17—H17 | 0.9300 |
O5B—C27B | 1.448 (10) | C18—H18 | 0.9300 |
N1—C1 | 1.315 (2) | C19—H19A | 0.9600 |
N1—C2 | 1.369 (2) | C19—H19B | 0.9600 |
N2—C3 | 1.341 (2) | C19—H19C | 0.9600 |
N2—C2 | 1.415 (2) | C20—C21 | 1.473 (3) |
N2—N3 | 1.419 (2) | C20—C28 | 1.492 (3) |
N3—C20 | 1.291 (2) | C21—C22 | 1.385 (3) |
C1—C4 | 1.424 (2) | C21—C26 | 1.391 (3) |
C1—C13 | 1.480 (3) | C22—C23 | 1.390 (3) |
C3—C4 | 1.353 (3) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.381 (3) |
C4—C5 | 1.501 (2) | C23—H23 | 0.9300 |
C5—C6 | 1.474 (3) | C24—C25 | 1.363 (3) |
C6—C7 | 1.390 (2) | C25—C26 | 1.370 (3) |
C6—C11 | 1.393 (2) | C25—H25 | 0.9300 |
C7—C8 | 1.370 (3) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27A—H27A | 0.9600 |
C8—C9 | 1.378 (3) | C27A—H27B | 0.9600 |
C8—H8 | 0.9300 | C27A—H27C | 0.9600 |
C9—C10 | 1.384 (3) | C27B—H27D | 0.9600 |
C10—C11 | 1.365 (3) | C27B—H27E | 0.9600 |
C10—H10 | 0.9300 | C27B—H27F | 0.9600 |
C11—H11 | 0.9300 | C28—H28A | 0.9600 |
C12—H12A | 0.9600 | C28—H28B | 0.9600 |
C12—H12B | 0.9600 | C28—H28C | 0.9600 |
C12—H12C | 0.9600 | ||
C9—O3—C12 | 118.36 (18) | O4—C16—C15 | 124.72 (17) |
C16—O4—C19 | 118.09 (16) | O4—C16—C17 | 115.83 (18) |
C24—O5A—C27A | 122.3 (9) | C15—C16—C17 | 119.45 (18) |
C24—O5B—C27B | 115.1 (7) | C18—C17—C16 | 120.62 (19) |
C1—N1—C2 | 120.47 (17) | C18—C17—H17 | 119.7 |
C3—N2—C2 | 120.43 (16) | C16—C17—H17 | 119.7 |
C3—N2—N3 | 116.72 (16) | C17—C18—C13 | 121.02 (18) |
C2—N2—N3 | 121.36 (14) | C17—C18—H18 | 119.5 |
C20—N3—N2 | 115.12 (17) | C13—C18—H18 | 119.5 |
N1—C1—C4 | 122.40 (17) | O4—C19—H19A | 109.5 |
N1—C1—C13 | 115.59 (17) | O4—C19—H19B | 109.5 |
C4—C1—C13 | 121.97 (16) | H19A—C19—H19B | 109.5 |
O1—C2—N1 | 124.14 (19) | O4—C19—H19C | 109.5 |
O1—C2—N2 | 119.71 (18) | H19A—C19—H19C | 109.5 |
N1—C2—N2 | 116.10 (16) | H19B—C19—H19C | 109.5 |
N2—C3—C4 | 121.45 (19) | N3—C20—C21 | 115.77 (19) |
N2—C3—H3 | 119.3 | N3—C20—C28 | 125.59 (18) |
C4—C3—H3 | 119.3 | C21—C20—C28 | 118.63 (18) |
C3—C4—C1 | 116.00 (17) | C22—C21—C26 | 117.03 (19) |
C3—C4—C5 | 117.15 (17) | C22—C21—C20 | 121.74 (19) |
C1—C4—C5 | 126.85 (17) | C26—C21—C20 | 121.2 (2) |
O2—C5—C6 | 121.51 (17) | C21—C22—C23 | 121.5 (2) |
O2—C5—C4 | 118.09 (18) | C21—C22—H22 | 119.3 |
C6—C5—C4 | 120.19 (16) | C23—C22—H22 | 119.3 |
C7—C6—C11 | 117.89 (19) | C24—C23—C22 | 119.1 (2) |
C7—C6—C5 | 119.02 (17) | C24—C23—H23 | 120.4 |
C11—C6—C5 | 122.99 (17) | C22—C23—H23 | 120.4 |
C8—C7—C6 | 121.84 (19) | C25—C24—O5B | 113.4 (3) |
C8—C7—H7 | 119.1 | C25—C24—O5A | 116.9 (5) |
C6—C7—H7 | 119.1 | C25—C24—C23 | 120.5 (2) |
C7—C8—C9 | 119.21 (19) | O5B—C24—C23 | 126.1 (3) |
C7—C8—H8 | 120.4 | O5A—C24—C23 | 122.6 (5) |
C9—C8—H8 | 120.4 | C24—C25—C26 | 119.7 (2) |
O3—C9—C8 | 124.44 (19) | C24—C25—H25 | 120.1 |
O3—C9—C10 | 115.54 (19) | C26—C25—H25 | 120.1 |
C8—C9—C10 | 120.0 (2) | C25—C26—C21 | 122.1 (2) |
C11—C10—C9 | 120.4 (2) | C25—C26—H26 | 119.0 |
C11—C10—H10 | 119.8 | C21—C26—H26 | 119.0 |
C9—C10—H10 | 119.8 | O5A—C27A—H27A | 109.5 |
C10—C11—C6 | 120.60 (18) | O5A—C27A—H27B | 109.5 |
C10—C11—H11 | 119.7 | H27A—C27A—H27B | 109.5 |
C6—C11—H11 | 119.7 | O5A—C27A—H27C | 109.5 |
O3—C12—H12A | 109.5 | H27A—C27A—H27C | 109.5 |
O3—C12—H12B | 109.5 | H27B—C27A—H27C | 109.5 |
H12A—C12—H12B | 109.5 | O5B—C27B—H27D | 109.5 |
O3—C12—H12C | 109.5 | O5B—C27B—H27E | 109.5 |
H12A—C12—H12C | 109.5 | H27D—C27B—H27E | 109.5 |
H12B—C12—H12C | 109.5 | O5B—C27B—H27F | 109.5 |
C18—C13—C14 | 117.96 (18) | H27D—C27B—H27F | 109.5 |
C18—C13—C1 | 119.71 (16) | H27E—C27B—H27F | 109.5 |
C14—C13—C1 | 122.31 (17) | C20—C28—H28A | 109.5 |
C15—C14—C13 | 121.53 (18) | C20—C28—H28B | 109.5 |
C15—C14—H14 | 119.2 | H28A—C28—H28B | 109.5 |
C13—C14—H14 | 119.2 | C20—C28—H28C | 109.5 |
C16—C15—C14 | 119.40 (18) | H28A—C28—H28C | 109.5 |
C16—C15—H15 | 120.3 | H28B—C28—H28C | 109.5 |
C14—C15—H15 | 120.3 | ||
C3—N2—N3—C20 | 130.76 (18) | C4—C1—C13—C18 | 143.52 (19) |
C2—N2—N3—C20 | −63.1 (2) | N1—C1—C13—C14 | 140.02 (19) |
C2—N1—C1—C4 | −1.2 (3) | C4—C1—C13—C14 | −37.7 (3) |
C2—N1—C1—C13 | −178.93 (18) | C18—C13—C14—C15 | −0.7 (3) |
C1—N1—C2—O1 | −167.12 (19) | C1—C13—C14—C15 | −179.5 (2) |
C1—N1—C2—N2 | 15.6 (3) | C13—C14—C15—C16 | −0.5 (3) |
C3—N2—C2—O1 | 162.20 (19) | C19—O4—C16—C15 | 8.0 (3) |
N3—N2—C2—O1 | −3.4 (3) | C19—O4—C16—C17 | −172.4 (2) |
C3—N2—C2—N1 | −20.4 (3) | C14—C15—C16—O4 | −179.3 (2) |
N3—N2—C2—N1 | 174.02 (17) | C14—C15—C16—C17 | 1.1 (3) |
C2—N2—C3—C4 | 10.4 (3) | O4—C16—C17—C18 | 179.9 (2) |
N3—N2—C3—C4 | 176.60 (18) | C15—C16—C17—C18 | −0.5 (3) |
N2—C3—C4—C1 | 4.4 (3) | C16—C17—C18—C13 | −0.7 (3) |
N2—C3—C4—C5 | −175.38 (17) | C14—C13—C18—C17 | 1.3 (3) |
N1—C1—C4—C3 | −9.2 (3) | C1—C13—C18—C17 | −179.9 (2) |
C13—C1—C4—C3 | 168.30 (19) | N2—N3—C20—C21 | 178.29 (14) |
N1—C1—C4—C5 | 170.45 (19) | N2—N3—C20—C28 | −2.7 (3) |
C13—C1—C4—C5 | −12.0 (3) | N3—C20—C21—C22 | 5.9 (3) |
C3—C4—C5—O2 | −48.0 (3) | C28—C20—C21—C22 | −173.17 (18) |
C1—C4—C5—O2 | 132.3 (2) | N3—C20—C21—C26 | −173.72 (17) |
C3—C4—C5—C6 | 126.9 (2) | C28—C20—C21—C26 | 7.2 (3) |
C1—C4—C5—C6 | −52.8 (3) | C26—C21—C22—C23 | −0.3 (3) |
O2—C5—C6—C7 | −10.4 (3) | C20—C21—C22—C23 | −179.92 (18) |
C4—C5—C6—C7 | 174.92 (18) | C21—C22—C23—C24 | 1.5 (3) |
O2—C5—C6—C11 | 166.02 (19) | C27B—O5B—C24—C25 | −165.4 (12) |
C4—C5—C6—C11 | −8.7 (3) | C27B—O5B—C24—O5A | 66 (8) |
C11—C6—C7—C8 | 0.3 (3) | C27B—O5B—C24—C23 | 11.8 (16) |
C5—C6—C7—C8 | 176.88 (19) | C27A—O5A—C24—C25 | 161.1 (13) |
C6—C7—C8—C9 | 0.0 (3) | C27A—O5A—C24—O5B | −145 (10) |
C12—O3—C9—C8 | −2.8 (4) | C27A—O5A—C24—C23 | −16.5 (17) |
C12—O3—C9—C10 | 177.1 (2) | C22—C23—C24—C25 | −1.9 (3) |
C7—C8—C9—O3 | 179.4 (2) | C22—C23—C24—O5B | −178.9 (8) |
C7—C8—C9—C10 | −0.5 (3) | C22—C23—C24—O5A | 175.5 (7) |
O3—C9—C10—C11 | −179.3 (2) | O5B—C24—C25—C26 | 178.5 (7) |
C8—C9—C10—C11 | 0.6 (3) | O5A—C24—C25—C26 | −176.4 (7) |
C9—C10—C11—C6 | −0.2 (3) | C23—C24—C25—C26 | 1.2 (3) |
C7—C6—C11—C10 | −0.2 (3) | C24—C25—C26—C21 | 0.1 (3) |
C5—C6—C11—C10 | −176.6 (2) | C22—C21—C26—C25 | −0.5 (3) |
N1—C1—C13—C18 | −38.8 (3) | C20—C21—C26—C25 | 179.14 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28A···O1 | 0.96 | 2.56 | 2.939 (3) | 104 |
C28—H28A···N2 | 0.96 | 2.33 | 2.763 (3) | 107 |
C27A—H27B···O1i | 0.96 | 2.52 | 3.308 (16) | 140 |
C7—H7···O2ii | 0.93 | 2.58 | 3.358 (2) | 142 |
C11—H11···O1iii | 0.93 | 2.47 | 3.307 (2) | 150 |
C19—H19A···O2iv | 0.96 | 2.40 | 3.217 (3) | 143 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+2, −z; (iv) x, y+1, z. |
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