Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023574/wk2049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023574/wk2049Isup2.hkl |
CCDC reference: 651499
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.154
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H4O .. H5O .. 2.00 Ang.
Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3554 Count of symmetry unique reflns 3561 Completeness (_total/calc) 99.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP.
C28H41NO6 | F(000) = 1056 |
Mr = 487.62 | Dx = 1.200 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3554 reflections |
a = 5.9940 (12) Å | θ = 1.4–27.5° |
b = 15.342 (3) Å | µ = 0.08 mm−1 |
c = 29.361 (6) Å | T = 183 K |
V = 2700.0 (9) Å3 | Prism, colourless |
Z = 4 | 0.7 × 0.7 × 0.4 mm |
Nonius KappaCCD diffractometer | 2415 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.072 |
Graphite monochromator | θmax = 27.5°, θmin = 1.4° |
φ and ω scans | h = −7→7 |
18295 measured reflections | k = −19→17 |
3554 independent reflections | l = −34→38 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom & difmap |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + (0.0906P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.006 |
3554 reflections | Δρmax = 0.32 e Å−3 |
331 parameters | Δρmin = −0.47 e Å−3 |
0 restraints | Absolute structure: determined by NMR |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
Experimental. Melting points are given uncorrected and were determined via a VEB Analytik Dresden HMK 72/41555. Infrared spectra were collected on a Bruker IFS55/Equinox spectrometer. 1H NMR, 13C NMR, 1H,1H COSY and 1H,13C HSQC experiments were carried out on Bruker Avance 200 and 400 MHz s pectrometers. Mass spectra were measured on a MAT95XL Finnigan instrument. Elemental analyses were determined on LECO CHN/932 and VARIO EL III elemental analyzers. Benzyl 2-deoxy-2-(3,5-di-tert-butyl]-salicylideneamino-α-D- glucopyranoside: IR (KBr): 3494, 3401, 3276 (ν O–H); 3066, 3027 (ν C–H arom.); 2962 (νas CH3); 2870 (νs CH2); 1628 (ν CH=N); 1597, 1498 (ν C=C); 1469, 1455, 1441 (δas CH3, δ CH2); 1392, 1362 (δs CH3); 1335; 1307; 1271, 1251, 1207, 1158, 1135, 1083, 1043, 1024, 1007, 983 (ν C–O); 880; 850; 827; 806; 772; 739; 731; 712; 696; 645; 530; 514 cm-1. 1H NMR (400 MHz, DMSO-d6, 298 K): 1.27 and 1.43 (2 s, each 9 H, H methyl); 3.22–3.28 (m, 1 H, H4); 3.26 (dd, 3 J21 = 3.6 Hz, 3 J23 = 9.5 Hz, 1 H, H2); 3.54–3.64 (m, 2 H, H5 and H6a); 3.69–3.71 (m, 2 H, H3 and H6b); 4.51 and 4.74 (2 d, 2 J7a7b = 12.4 Hz, each 1 H, H7a and H7b); 4.60 (dd, 3Jav = 5.9 Hz, 1 H, OH6); 4.86 (d, 3 J12 = 3.7 Hz, 1 H, H1); 5.05 (d, 3 J4OH4 = 5.9 Hz, 1 H, OH4); 5.11 (d, 3 J3OH3 = 5.9 Hz, 1 H, OH3); 7.25–7.32 (m, 3 H, H ph); 7.41–7.43 (m, 2 H, H ph); 8.49 (s, 1 H, H14); 14.70 (s, 1 H, OH20) p.p.m.. 13 C NMR (60 MHz, DMSO-d6, 298 K): 29.2 and 31.3 (C22—C24 and C26—C28); 33.8 and 34.6 (C21 and C25); 60.9 (C6); 67.9 (C7); 70.2 and 71.4 (C2, C3 and C4); 73.4 (C5); 97.5 (C1); 117.6, 126.1, 126.2, 127.4, 128.0, 135.8, 137.9 and 139.0 (C ph); 158.6 (C20) 168.1 (C14) p.p.m.. ESI-MS: m/z (%) = 486 [M+H]+ (3), 508 [M+Na]+ (100). Benzyl 2-deoxy-2-[3,5-di-tert-butyl]-salicylamino-α-D-glucopyranoside: IR (KBr): 3513 (ν O–H); 3324 (ν N–H); 3031, 3000 (ν C–H arom.); 2954 (νas CH3); 2909 (νas CH2); 2870 (νs CH2); 2835 (νs CH3); 1481; 1456 (δas CH3, δ CH2); 1360 (δs CH3); 1238; 1127, 1096, 1063, 987 (ν C–O); 763; 702 cm-1. 1H NMR (400 MHz, DMSO-d6, 298 K): 1.22 and 1.35 (2 s, 18 H, H methyl); 2.49–2.53 (m, 1 H, H2); 2.73 (d, 3 J = 5.4 Hz, 1 H, N—H); 3.13 (dd, 3 J43 = 3 J45 = 9.3 Hz, 1 H, H4); 3.41–3.50 (m, 3 H, H3, H5 and H6); 3.66 (dd, 3 J65 = 2 J6a6e = 11.3 Hz, 1 H, H6); 3.81–3.86 (m, 2 H, H14); 4.46 and 4.67 (2 d, 2 J7a7b = 11.7 Hz, each 1 H, H7a and H7b); 4.53 (s, 1 H, OH6); 4.95 (s, 1 H, OH4); 4.98 (d, 3 J12 = 3.7 Hz, 1 H, H1); 5.02 (s, 1 H, OH3); 6.80 (d, J = 2.2 Hz, 1 H, H ph); 7.07 (d, J = 2.2 Hz, 1 H, H ph); 7.28–7.36 (m, 3 H, H ph); 7.45–7.47 (m, 2 H, H ph) p.p.m.. 13 C NMR (100 MHz, DMSO-d6, 298 K): 29.5 and 31.5 (C22—C24 and C26—C28); 33.7 and 34.4 (C21 and C25); 50.8 (C14); 60.9 (C6); 61.1 (C2); 68.2 (C7); 70.5 (C4); 72.2 and 73.1 (C3 and C5); 95.4 (C1); 121.6, 122.9, 123.0, 127.5, 128.1, 128.2, 134.6, 137.7 and 139.3 (C ph); 154.4 (C20) p.p.m.. ESI-MS: m/z (%) = [M+H]+ (4), [M+Na]+ (40). C28H41NO6 (487.63 g/mol): calcd. C 68.97%, H 8.47%, N 2.87%; found C 69.09%, H 8.40%, N 2.72%. |
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 | ||
N | −0.1454 (5) | 0.48491 (18) | 0.15860 (9) | 0.0273 (6) | |
H1N | −0.270 (9) | 0.510 (3) | 0.1689 (14) | 0.061 (14)* | |
O1 | 0.2534 (4) | 0.54219 (13) | 0.06620 (7) | 0.0235 (5) | |
O2 | 0.0791 (4) | 0.41054 (13) | 0.08674 (7) | 0.0281 (5) | |
O3 | −0.3626 (4) | 0.62236 (15) | 0.11413 (8) | 0.0324 (6) | |
H3O | −0.4855 | 0.6195 | 0.1005 | 0.049* | |
O4 | −0.2409 (4) | 0.65053 (15) | 0.01987 (8) | 0.0300 (5) | |
H4O | −0.2120 | 0.7016 | 0.0114 | 0.045* | |
O5 | 0.3306 (4) | 0.68642 (15) | 0.00840 (9) | 0.0350 (6) | |
H5O | 0.4628 | 0.6750 | 0.0158 | 0.053* | |
O6 | −0.2685 (5) | 0.31511 (16) | 0.16507 (7) | 0.0381 (6) | |
H6O | −0.2339 | 0.3615 | 0.1516 | 0.066 (15)* | |
C1 | 0.1599 (6) | 0.49044 (19) | 0.10197 (10) | 0.0242 (7) | |
H1 | 0.2787 | 0.4793 | 0.1252 | 0.029* | |
C2 | −0.0323 (5) | 0.53937 (19) | 0.12518 (10) | 0.0223 (7) | |
H2 | 0.0312 | 0.5911 | 0.1413 | 0.027* | |
C3 | −0.2005 (5) | 0.5718 (2) | 0.09020 (10) | 0.0230 (7) | |
H3 | −0.2760 | 0.5206 | 0.0758 | 0.028* | |
C4 | −0.0827 (5) | 0.6240 (2) | 0.05355 (10) | 0.0221 (7) | |
H4 | −0.0103 | 0.6764 | 0.0674 | 0.027* | |
C5 | 0.0936 (5) | 0.5663 (2) | 0.03155 (10) | 0.0223 (7) | |
H5 | 0.0203 | 0.5123 | 0.0197 | 0.027* | |
C6 | 0.2226 (6) | 0.6088 (2) | −0.00653 (11) | 0.0293 (8) | |
H6A | 0.3357 | 0.5674 | −0.0182 | 0.035* | |
H6B | 0.1195 | 0.6229 | −0.0318 | 0.035* | |
C7 | 0.2506 (7) | 0.3496 (2) | 0.07329 (12) | 0.0367 (9) | |
H7A | 0.1986 | 0.2896 | 0.0796 | 0.044* | |
H7B | 0.3858 | 0.3601 | 0.0919 | 0.044* | |
C8 | 0.3108 (6) | 0.3570 (2) | 0.02352 (12) | 0.0294 (8) | |
C9 | 0.1556 (7) | 0.3356 (2) | −0.00956 (12) | 0.0382 (9) | |
H9 | 0.0112 | 0.3164 | −0.0007 | 0.046* | |
C10 | 0.2082 (7) | 0.3418 (3) | −0.05529 (14) | 0.0467 (10) | |
H10 | 0.1003 | 0.3268 | −0.0777 | 0.056* | |
C11 | 0.4168 (7) | 0.3697 (3) | −0.06849 (13) | 0.0452 (10) | |
H11 | 0.4523 | 0.3745 | −0.0999 | 0.054* | |
C12 | 0.5731 (7) | 0.3904 (2) | −0.03612 (13) | 0.0395 (9) | |
H12 | 0.7171 | 0.4095 | −0.0452 | 0.047* | |
C13 | 0.5223 (6) | 0.3837 (2) | 0.00983 (12) | 0.0345 (9) | |
H13 | 0.6321 | 0.3974 | 0.0320 | 0.041* | |
C14 | −0.0054 (6) | 0.4564 (2) | 0.19685 (11) | 0.0325 (8) | |
H14A | 0.0479 | 0.5081 | 0.2139 | 0.039* | |
H14B | 0.1265 | 0.4250 | 0.1850 | 0.039* | |
C15 | −0.1334 (6) | 0.3977 (2) | 0.22845 (11) | 0.0289 (8) | |
C16 | −0.1180 (6) | 0.4094 (2) | 0.27534 (11) | 0.0301 (8) | |
H16 | −0.0368 | 0.4578 | 0.2869 | 0.036* | |
C17 | −0.2178 (6) | 0.3524 (2) | 0.30569 (11) | 0.0276 (8) | |
C18 | −0.3424 (6) | 0.2842 (2) | 0.28748 (11) | 0.0277 (8) | |
H18 | −0.4160 | 0.2458 | 0.3079 | 0.033* | |
C19 | −0.3648 (6) | 0.2693 (2) | 0.24081 (11) | 0.0272 (7) | |
C20 | −0.2585 (6) | 0.3280 (2) | 0.21135 (10) | 0.0282 (8) | |
C21 | −0.1843 (6) | 0.3652 (2) | 0.35717 (11) | 0.0318 (8) | |
C22 | −0.2772 (10) | 0.4544 (2) | 0.37159 (13) | 0.0560 (13) | |
H22A | −0.4363 | 0.4575 | 0.3641 | 0.084* | |
H22B | −0.1970 | 0.5006 | 0.3554 | 0.084* | |
H22C | −0.2576 | 0.4619 | 0.4045 | 0.084* | |
C23 | 0.0631 (7) | 0.3579 (4) | 0.36774 (14) | 0.0581 (13) | |
H23A | 0.0858 | 0.3616 | 0.4007 | 0.087* | |
H23B | 0.1436 | 0.4055 | 0.3527 | 0.087* | |
H23C | 0.1195 | 0.3019 | 0.3566 | 0.087* | |
C24 | −0.3073 (6) | 0.2964 (2) | 0.38537 (11) | 0.0348 (9) | |
H24A | −0.4676 | 0.3000 | 0.3792 | 0.052* | |
H24B | −0.2803 | 0.3069 | 0.4178 | 0.052* | |
H24C | −0.2525 | 0.2383 | 0.3772 | 0.052* | |
C25 | −0.4946 (7) | 0.1907 (2) | 0.22253 (11) | 0.0347 (9) | |
C26 | −0.5971 (8) | 0.1356 (3) | 0.26096 (13) | 0.0527 (12) | |
H26A | −0.6731 | 0.0850 | 0.2479 | 0.079* | |
H26B | −0.7048 | 0.1710 | 0.2780 | 0.079* | |
H26C | −0.4788 | 0.1159 | 0.2816 | 0.079* | |
C27 | −0.6857 (7) | 0.2190 (3) | 0.19140 (14) | 0.0469 (10) | |
H27A | −0.6262 | 0.2541 | 0.1663 | 0.070* | |
H27B | −0.7929 | 0.2537 | 0.2089 | 0.070* | |
H27C | −0.7604 | 0.1673 | 0.1791 | 0.070* | |
C28 | −0.3310 (8) | 0.1310 (2) | 0.19638 (14) | 0.0482 (11) | |
H28A | −0.2723 | 0.1622 | 0.1698 | 0.072* | |
H28B | −0.4096 | 0.0785 | 0.1862 | 0.072* | |
H28C | −0.2075 | 0.1145 | 0.2165 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N | 0.0255 (16) | 0.0318 (15) | 0.0245 (15) | 0.0009 (14) | 0.0045 (13) | 0.0062 (12) |
O1 | 0.0195 (11) | 0.0264 (11) | 0.0245 (11) | −0.0009 (10) | 0.0000 (9) | 0.0068 (9) |
O2 | 0.0304 (13) | 0.0203 (11) | 0.0336 (13) | 0.0000 (10) | 0.0072 (10) | 0.0016 (9) |
O3 | 0.0251 (13) | 0.0354 (13) | 0.0367 (14) | 0.0074 (12) | 0.0076 (11) | −0.0014 (11) |
O4 | 0.0235 (12) | 0.0286 (12) | 0.0380 (14) | −0.0003 (11) | −0.0054 (11) | 0.0102 (10) |
O5 | 0.0195 (12) | 0.0318 (13) | 0.0537 (16) | 0.0007 (11) | 0.0033 (11) | 0.0193 (12) |
O6 | 0.0583 (17) | 0.0347 (13) | 0.0213 (12) | −0.0119 (14) | −0.0021 (12) | 0.0029 (11) |
C1 | 0.0250 (17) | 0.0233 (16) | 0.0241 (16) | −0.0035 (15) | 0.0025 (14) | 0.0072 (13) |
C2 | 0.0241 (17) | 0.0213 (16) | 0.0215 (16) | −0.0029 (14) | 0.0020 (13) | 0.0036 (13) |
C3 | 0.0216 (17) | 0.0225 (15) | 0.0251 (17) | 0.0005 (14) | 0.0035 (13) | −0.0019 (13) |
C4 | 0.0175 (16) | 0.0241 (16) | 0.0248 (16) | −0.0012 (14) | −0.0023 (13) | 0.0008 (13) |
C5 | 0.0225 (17) | 0.0233 (15) | 0.0210 (16) | −0.0020 (14) | −0.0026 (13) | 0.0037 (13) |
C6 | 0.0256 (18) | 0.0335 (18) | 0.0289 (18) | 0.0023 (16) | 0.0057 (15) | 0.0076 (15) |
C7 | 0.045 (2) | 0.0248 (17) | 0.040 (2) | 0.0103 (18) | 0.0043 (18) | 0.0030 (15) |
C8 | 0.0328 (19) | 0.0192 (16) | 0.0363 (19) | 0.0052 (15) | 0.0034 (16) | −0.0008 (14) |
C9 | 0.032 (2) | 0.038 (2) | 0.044 (2) | 0.0010 (18) | 0.0034 (18) | −0.0029 (17) |
C10 | 0.040 (2) | 0.057 (3) | 0.043 (2) | 0.001 (2) | −0.0074 (19) | −0.006 (2) |
C11 | 0.050 (2) | 0.052 (2) | 0.033 (2) | 0.006 (2) | 0.0041 (18) | −0.0015 (19) |
C12 | 0.031 (2) | 0.037 (2) | 0.051 (2) | 0.0009 (18) | 0.0110 (18) | 0.0033 (18) |
C13 | 0.034 (2) | 0.0301 (18) | 0.040 (2) | 0.0019 (17) | −0.0027 (17) | −0.0036 (16) |
C14 | 0.035 (2) | 0.0358 (19) | 0.0269 (18) | −0.0088 (17) | −0.0009 (15) | 0.0054 (15) |
C15 | 0.0323 (19) | 0.0288 (17) | 0.0255 (18) | −0.0032 (16) | −0.0008 (15) | 0.0033 (14) |
C16 | 0.035 (2) | 0.0301 (18) | 0.0255 (18) | −0.0075 (17) | −0.0033 (16) | 0.0031 (14) |
C17 | 0.0286 (18) | 0.0304 (17) | 0.0239 (17) | −0.0012 (16) | −0.0012 (15) | 0.0061 (14) |
C18 | 0.0322 (19) | 0.0258 (16) | 0.0251 (17) | −0.0028 (16) | 0.0011 (15) | 0.0035 (14) |
C19 | 0.0304 (18) | 0.0256 (16) | 0.0258 (17) | −0.0010 (15) | −0.0022 (15) | 0.0004 (14) |
C20 | 0.0345 (18) | 0.0336 (18) | 0.0165 (16) | 0.0003 (18) | −0.0002 (14) | 0.0012 (13) |
C21 | 0.040 (2) | 0.0334 (18) | 0.0216 (17) | −0.0047 (17) | −0.0017 (15) | 0.0039 (15) |
C22 | 0.101 (4) | 0.038 (2) | 0.030 (2) | −0.002 (3) | −0.002 (2) | −0.0032 (17) |
C23 | 0.042 (2) | 0.099 (4) | 0.033 (2) | −0.019 (3) | −0.0114 (19) | 0.012 (2) |
C24 | 0.040 (2) | 0.042 (2) | 0.0232 (17) | 0.0000 (18) | −0.0019 (16) | 0.0048 (15) |
C25 | 0.045 (2) | 0.0310 (18) | 0.0283 (19) | −0.0086 (18) | −0.0026 (16) | 0.0015 (15) |
C26 | 0.071 (3) | 0.046 (2) | 0.041 (2) | −0.028 (2) | 0.000 (2) | 0.0049 (18) |
C27 | 0.042 (2) | 0.050 (2) | 0.049 (2) | −0.010 (2) | −0.012 (2) | 0.002 (2) |
C28 | 0.061 (3) | 0.032 (2) | 0.051 (2) | −0.007 (2) | −0.001 (2) | −0.0084 (18) |
N—C2 | 1.456 (4) | C12—H12 | 0.9500 |
N—C14 | 1.468 (4) | C13—H13 | 0.9500 |
N—H1N | 0.89 (5) | C14—C15 | 1.503 (4) |
O1—C1 | 1.431 (4) | C14—H14A | 0.9900 |
O1—C5 | 1.446 (4) | C14—H14B | 0.9900 |
O2—C1 | 1.392 (4) | C15—C16 | 1.391 (4) |
O2—C7 | 1.445 (4) | C15—C20 | 1.400 (5) |
O3—C3 | 1.428 (4) | C16—C17 | 1.385 (4) |
O3—H3O | 0.8400 | C16—H16 | 0.9500 |
O4—C4 | 1.430 (4) | C17—C18 | 1.392 (5) |
O4—H4O | 0.8400 | C17—C21 | 1.537 (5) |
O5—C6 | 1.425 (4) | C18—C19 | 1.396 (5) |
O5—H5O | 0.8400 | C18—H18 | 0.9500 |
O6—C20 | 1.374 (4) | C19—C20 | 1.402 (4) |
O6—H6O | 0.8400 | C19—C25 | 1.532 (5) |
C1—C2 | 1.535 (4) | C21—C23 | 1.519 (6) |
C1—H1 | 1.0000 | C21—C24 | 1.531 (5) |
C2—C3 | 1.523 (4) | C21—C22 | 1.536 (5) |
C2—H2 | 1.0000 | C22—H22A | 0.9800 |
C3—C4 | 1.515 (4) | C22—H22B | 0.9800 |
C3—H3 | 1.0000 | C22—H22C | 0.9800 |
C4—C5 | 1.522 (4) | C23—H23A | 0.9800 |
C4—H4 | 1.0000 | C23—H23B | 0.9800 |
C5—C6 | 1.508 (4) | C23—H23C | 0.9800 |
C5—H5 | 1.0000 | C24—H24A | 0.9800 |
C6—H6A | 0.9900 | C24—H24B | 0.9800 |
C6—H6B | 0.9900 | C24—H24C | 0.9800 |
C7—C8 | 1.509 (5) | C25—C27 | 1.528 (5) |
C7—H7A | 0.9900 | C25—C26 | 1.538 (5) |
C7—H7B | 0.9900 | C25—C28 | 1.546 (5) |
C8—C9 | 1.384 (5) | C26—H26A | 0.9800 |
C8—C13 | 1.392 (5) | C26—H26B | 0.9800 |
C9—C10 | 1.383 (5) | C26—H26C | 0.9800 |
C9—H9 | 0.9500 | C27—H27A | 0.9800 |
C10—C11 | 1.377 (6) | C27—H27B | 0.9800 |
C10—H10 | 0.9500 | C27—H27C | 0.9800 |
C11—C12 | 1.372 (6) | C28—H28A | 0.9800 |
C11—H11 | 0.9500 | C28—H28B | 0.9800 |
C12—C13 | 1.387 (5) | C28—H28C | 0.9800 |
C2—N—C14 | 114.9 (3) | C15—C14—H14A | 109.4 |
C2—N—H1N | 112 (3) | N—C14—H14B | 109.4 |
C14—N—H1N | 110 (3) | C15—C14—H14B | 109.4 |
C1—O1—C5 | 113.5 (2) | H14A—C14—H14B | 108.0 |
C1—O2—C7 | 114.2 (3) | C16—C15—C20 | 119.3 (3) |
C3—O3—H3O | 109.5 | C16—C15—C14 | 120.0 (3) |
C4—O4—H4O | 109.5 | C20—C15—C14 | 120.6 (3) |
C6—O5—H5O | 109.5 | C17—C16—C15 | 121.8 (3) |
C20—O6—H6O | 109.5 | C17—C16—H16 | 119.1 |
O2—C1—O1 | 112.9 (2) | C15—C16—H16 | 119.1 |
O2—C1—C2 | 108.2 (3) | C16—C17—C18 | 117.3 (3) |
O1—C1—C2 | 110.4 (2) | C16—C17—C21 | 119.7 (3) |
O2—C1—H1 | 108.4 | C18—C17—C21 | 123.0 (3) |
O1—C1—H1 | 108.4 | C17—C18—C19 | 123.5 (3) |
C2—C1—H1 | 108.4 | C17—C18—H18 | 118.2 |
N—C2—C3 | 109.5 (3) | C19—C18—H18 | 118.2 |
N—C2—C1 | 111.6 (2) | C18—C19—C20 | 117.2 (3) |
C3—C2—C1 | 111.0 (2) | C18—C19—C25 | 121.5 (3) |
N—C2—H2 | 108.2 | C20—C19—C25 | 121.3 (3) |
C3—C2—H2 | 108.2 | O6—C20—C15 | 119.2 (3) |
C1—C2—H2 | 108.2 | O6—C20—C19 | 119.9 (3) |
O3—C3—C4 | 112.3 (2) | C15—C20—C19 | 120.9 (3) |
O3—C3—C2 | 107.2 (2) | C23—C21—C24 | 108.0 (3) |
C4—C3—C2 | 110.0 (3) | C23—C21—C22 | 111.3 (4) |
O3—C3—H3 | 109.1 | C24—C21—C22 | 106.9 (3) |
C4—C3—H3 | 109.1 | C23—C21—C17 | 108.6 (3) |
C2—C3—H3 | 109.1 | C24—C21—C17 | 112.4 (3) |
O4—C4—C3 | 109.4 (2) | C22—C21—C17 | 109.7 (3) |
O4—C4—C5 | 109.4 (2) | C21—C22—H22A | 109.5 |
C3—C4—C5 | 108.5 (2) | C21—C22—H22B | 109.5 |
O4—C4—H4 | 109.8 | H22A—C22—H22B | 109.5 |
C3—C4—H4 | 109.8 | C21—C22—H22C | 109.5 |
C5—C4—H4 | 109.8 | H22A—C22—H22C | 109.5 |
O1—C5—C6 | 107.0 (3) | H22B—C22—H22C | 109.5 |
O1—C5—C4 | 108.1 (2) | C21—C23—H23A | 109.5 |
C6—C5—C4 | 114.8 (3) | C21—C23—H23B | 109.5 |
O1—C5—H5 | 108.9 | H23A—C23—H23B | 109.5 |
C6—C5—H5 | 108.9 | C21—C23—H23C | 109.5 |
C4—C5—H5 | 108.9 | H23A—C23—H23C | 109.5 |
O5—C6—C5 | 111.5 (3) | H23B—C23—H23C | 109.5 |
O5—C6—H6A | 109.3 | C21—C24—H24A | 109.5 |
C5—C6—H6A | 109.3 | C21—C24—H24B | 109.5 |
O5—C6—H6B | 109.3 | H24A—C24—H24B | 109.5 |
C5—C6—H6B | 109.3 | C21—C24—H24C | 109.5 |
H6A—C6—H6B | 108.0 | H24A—C24—H24C | 109.5 |
O2—C7—C8 | 112.7 (3) | H24B—C24—H24C | 109.5 |
O2—C7—H7A | 109.0 | C27—C25—C19 | 111.5 (3) |
C8—C7—H7A | 109.0 | C27—C25—C26 | 107.2 (3) |
O2—C7—H7B | 109.0 | C19—C25—C26 | 112.2 (3) |
C8—C7—H7B | 109.0 | C27—C25—C28 | 110.3 (3) |
H7A—C7—H7B | 107.8 | C19—C25—C28 | 108.5 (3) |
C9—C8—C13 | 118.7 (3) | C26—C25—C28 | 107.0 (3) |
C9—C8—C7 | 120.0 (3) | C25—C26—H26A | 109.5 |
C13—C8—C7 | 121.3 (3) | C25—C26—H26B | 109.5 |
C10—C9—C8 | 120.8 (4) | H26A—C26—H26B | 109.5 |
C10—C9—H9 | 119.6 | C25—C26—H26C | 109.5 |
C8—C9—H9 | 119.6 | H26A—C26—H26C | 109.5 |
C11—C10—C9 | 120.1 (4) | H26B—C26—H26C | 109.5 |
C11—C10—H10 | 119.9 | C25—C27—H27A | 109.5 |
C9—C10—H10 | 119.9 | C25—C27—H27B | 109.5 |
C12—C11—C10 | 119.8 (4) | H27A—C27—H27B | 109.5 |
C12—C11—H11 | 120.1 | C25—C27—H27C | 109.5 |
C10—C11—H11 | 120.1 | H27A—C27—H27C | 109.5 |
C11—C12—C13 | 120.4 (4) | H27B—C27—H27C | 109.5 |
C11—C12—H12 | 119.8 | C25—C28—H28A | 109.5 |
C13—C12—H12 | 119.8 | C25—C28—H28B | 109.5 |
C12—C13—C8 | 120.2 (3) | H28A—C28—H28B | 109.5 |
C12—C13—H13 | 119.9 | C25—C28—H28C | 109.5 |
C8—C13—H13 | 119.9 | H28A—C28—H28C | 109.5 |
N—C14—C15 | 111.0 (3) | H28B—C28—H28C | 109.5 |
N—C14—H14A | 109.4 |
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