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The title compound, C28H41NO6, was obtained by reduction of benzyl 2-de­oxy-2-(3,5-di-tert-but­ylsalicylideneamino)-α-D-gluco­pyran­oside. The benzyl substituent is in an axial position, whereas the 3,5-di-tert-butyl­salicylamino substituent and the hydroxyl groups are in equatorial positions. The enantio­merically pure title compound is a potential O,N,O-chelate ligand suitable as a precursor for chiral transition metal complexes. The absolute configuration was determined by NMR experiments.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023574/wk2049sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023574/wk2049Isup2.hkl
Contains datablock I

CCDC reference: 651499

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](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

Computing details top

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.

Benzyl 2-deoxy-2-(3,5-ditert-butylsalicylamino)-α-D-glucopyranoside top
Crystal data top
C28H41NO6F(000) = 1056
Mr = 487.62Dx = 1.200 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3554 reflections
a = 5.9940 (12) Åθ = 1.4–27.5°
b = 15.342 (3) ŵ = 0.08 mm1
c = 29.361 (6) ÅT = 183 K
V = 2700.0 (9) Å3Prism, colourless
Z = 40.7 × 0.7 × 0.4 mm
Data collection top
Nonius KappaCCD
diffractometer
2415 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
Graphite monochromatorθmax = 27.5°, θmin = 1.4°
φ and ω scansh = 77
18295 measured reflectionsk = 1917
3554 independent reflectionsl = 3438
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom & difmap
R[F2 > 2σ(F2)] = 0.046H 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 reflectionsΔρmax = 0.32 e Å3
331 parametersΔρmin = 0.47 e Å3
0 restraintsAbsolute structure: determined by NMR
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (10)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N0.1454 (5)0.48491 (18)0.15860 (9)0.0273 (6)
H1N0.270 (9)0.510 (3)0.1689 (14)0.061 (14)*
O10.2534 (4)0.54219 (13)0.06620 (7)0.0235 (5)
O20.0791 (4)0.41054 (13)0.08674 (7)0.0281 (5)
O30.3626 (4)0.62236 (15)0.11413 (8)0.0324 (6)
H3O0.48550.61950.10050.049*
O40.2409 (4)0.65053 (15)0.01987 (8)0.0300 (5)
H4O0.21200.70160.01140.045*
O50.3306 (4)0.68642 (15)0.00840 (9)0.0350 (6)
H5O0.46280.67500.01580.053*
O60.2685 (5)0.31511 (16)0.16507 (7)0.0381 (6)
H6O0.23390.36150.15160.066 (15)*
C10.1599 (6)0.49044 (19)0.10197 (10)0.0242 (7)
H10.27870.47930.12520.029*
C20.0323 (5)0.53937 (19)0.12518 (10)0.0223 (7)
H20.03120.59110.14130.027*
C30.2005 (5)0.5718 (2)0.09020 (10)0.0230 (7)
H30.27600.52060.07580.028*
C40.0827 (5)0.6240 (2)0.05355 (10)0.0221 (7)
H40.01030.67640.06740.027*
C50.0936 (5)0.5663 (2)0.03155 (10)0.0223 (7)
H50.02030.51230.01970.027*
C60.2226 (6)0.6088 (2)0.00653 (11)0.0293 (8)
H6A0.33570.56740.01820.035*
H6B0.11950.62290.03180.035*
C70.2506 (7)0.3496 (2)0.07329 (12)0.0367 (9)
H7A0.19860.28960.07960.044*
H7B0.38580.36010.09190.044*
C80.3108 (6)0.3570 (2)0.02352 (12)0.0294 (8)
C90.1556 (7)0.3356 (2)0.00956 (12)0.0382 (9)
H90.01120.31640.00070.046*
C100.2082 (7)0.3418 (3)0.05529 (14)0.0467 (10)
H100.10030.32680.07770.056*
C110.4168 (7)0.3697 (3)0.06849 (13)0.0452 (10)
H110.45230.37450.09990.054*
C120.5731 (7)0.3904 (2)0.03612 (13)0.0395 (9)
H120.71710.40950.04520.047*
C130.5223 (6)0.3837 (2)0.00983 (12)0.0345 (9)
H130.63210.39740.03200.041*
C140.0054 (6)0.4564 (2)0.19685 (11)0.0325 (8)
H14A0.04790.50810.21390.039*
H14B0.12650.42500.18500.039*
C150.1334 (6)0.3977 (2)0.22845 (11)0.0289 (8)
C160.1180 (6)0.4094 (2)0.27534 (11)0.0301 (8)
H160.03680.45780.28690.036*
C170.2178 (6)0.3524 (2)0.30569 (11)0.0276 (8)
C180.3424 (6)0.2842 (2)0.28748 (11)0.0277 (8)
H180.41600.24580.30790.033*
C190.3648 (6)0.2693 (2)0.24081 (11)0.0272 (7)
C200.2585 (6)0.3280 (2)0.21135 (10)0.0282 (8)
C210.1843 (6)0.3652 (2)0.35717 (11)0.0318 (8)
C220.2772 (10)0.4544 (2)0.37159 (13)0.0560 (13)
H22A0.43630.45750.36410.084*
H22B0.19700.50060.35540.084*
H22C0.25760.46190.40450.084*
C230.0631 (7)0.3579 (4)0.36774 (14)0.0581 (13)
H23A0.08580.36160.40070.087*
H23B0.14360.40550.35270.087*
H23C0.11950.30190.35660.087*
C240.3073 (6)0.2964 (2)0.38537 (11)0.0348 (9)
H24A0.46760.30000.37920.052*
H24B0.28030.30690.41780.052*
H24C0.25250.23830.37720.052*
C250.4946 (7)0.1907 (2)0.22253 (11)0.0347 (9)
C260.5971 (8)0.1356 (3)0.26096 (13)0.0527 (12)
H26A0.67310.08500.24790.079*
H26B0.70480.17100.27800.079*
H26C0.47880.11590.28160.079*
C270.6857 (7)0.2190 (3)0.19140 (14)0.0469 (10)
H27A0.62620.25410.16630.070*
H27B0.79290.25370.20890.070*
H27C0.76040.16730.17910.070*
C280.3310 (8)0.1310 (2)0.19638 (14)0.0482 (11)
H28A0.27230.16220.16980.072*
H28B0.40960.07850.18620.072*
H28C0.20750.11450.21650.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0255 (16)0.0318 (15)0.0245 (15)0.0009 (14)0.0045 (13)0.0062 (12)
O10.0195 (11)0.0264 (11)0.0245 (11)0.0009 (10)0.0000 (9)0.0068 (9)
O20.0304 (13)0.0203 (11)0.0336 (13)0.0000 (10)0.0072 (10)0.0016 (9)
O30.0251 (13)0.0354 (13)0.0367 (14)0.0074 (12)0.0076 (11)0.0014 (11)
O40.0235 (12)0.0286 (12)0.0380 (14)0.0003 (11)0.0054 (11)0.0102 (10)
O50.0195 (12)0.0318 (13)0.0537 (16)0.0007 (11)0.0033 (11)0.0193 (12)
O60.0583 (17)0.0347 (13)0.0213 (12)0.0119 (14)0.0021 (12)0.0029 (11)
C10.0250 (17)0.0233 (16)0.0241 (16)0.0035 (15)0.0025 (14)0.0072 (13)
C20.0241 (17)0.0213 (16)0.0215 (16)0.0029 (14)0.0020 (13)0.0036 (13)
C30.0216 (17)0.0225 (15)0.0251 (17)0.0005 (14)0.0035 (13)0.0019 (13)
C40.0175 (16)0.0241 (16)0.0248 (16)0.0012 (14)0.0023 (13)0.0008 (13)
C50.0225 (17)0.0233 (15)0.0210 (16)0.0020 (14)0.0026 (13)0.0037 (13)
C60.0256 (18)0.0335 (18)0.0289 (18)0.0023 (16)0.0057 (15)0.0076 (15)
C70.045 (2)0.0248 (17)0.040 (2)0.0103 (18)0.0043 (18)0.0030 (15)
C80.0328 (19)0.0192 (16)0.0363 (19)0.0052 (15)0.0034 (16)0.0008 (14)
C90.032 (2)0.038 (2)0.044 (2)0.0010 (18)0.0034 (18)0.0029 (17)
C100.040 (2)0.057 (3)0.043 (2)0.001 (2)0.0074 (19)0.006 (2)
C110.050 (2)0.052 (2)0.033 (2)0.006 (2)0.0041 (18)0.0015 (19)
C120.031 (2)0.037 (2)0.051 (2)0.0009 (18)0.0110 (18)0.0033 (18)
C130.034 (2)0.0301 (18)0.040 (2)0.0019 (17)0.0027 (17)0.0036 (16)
C140.035 (2)0.0358 (19)0.0269 (18)0.0088 (17)0.0009 (15)0.0054 (15)
C150.0323 (19)0.0288 (17)0.0255 (18)0.0032 (16)0.0008 (15)0.0033 (14)
C160.035 (2)0.0301 (18)0.0255 (18)0.0075 (17)0.0033 (16)0.0031 (14)
C170.0286 (18)0.0304 (17)0.0239 (17)0.0012 (16)0.0012 (15)0.0061 (14)
C180.0322 (19)0.0258 (16)0.0251 (17)0.0028 (16)0.0011 (15)0.0035 (14)
C190.0304 (18)0.0256 (16)0.0258 (17)0.0010 (15)0.0022 (15)0.0004 (14)
C200.0345 (18)0.0336 (18)0.0165 (16)0.0003 (18)0.0002 (14)0.0012 (13)
C210.040 (2)0.0334 (18)0.0216 (17)0.0047 (17)0.0017 (15)0.0039 (15)
C220.101 (4)0.038 (2)0.030 (2)0.002 (3)0.002 (2)0.0032 (17)
C230.042 (2)0.099 (4)0.033 (2)0.019 (3)0.0114 (19)0.012 (2)
C240.040 (2)0.042 (2)0.0232 (17)0.0000 (18)0.0019 (16)0.0048 (15)
C250.045 (2)0.0310 (18)0.0283 (19)0.0086 (18)0.0026 (16)0.0015 (15)
C260.071 (3)0.046 (2)0.041 (2)0.028 (2)0.000 (2)0.0049 (18)
C270.042 (2)0.050 (2)0.049 (2)0.010 (2)0.012 (2)0.002 (2)
C280.061 (3)0.032 (2)0.051 (2)0.007 (2)0.001 (2)0.0084 (18)
Geometric parameters (Å, º) top
N—C21.456 (4)C12—H120.9500
N—C141.468 (4)C13—H130.9500
N—H1N0.89 (5)C14—C151.503 (4)
O1—C11.431 (4)C14—H14A0.9900
O1—C51.446 (4)C14—H14B0.9900
O2—C11.392 (4)C15—C161.391 (4)
O2—C71.445 (4)C15—C201.400 (5)
O3—C31.428 (4)C16—C171.385 (4)
O3—H3O0.8400C16—H160.9500
O4—C41.430 (4)C17—C181.392 (5)
O4—H4O0.8400C17—C211.537 (5)
O5—C61.425 (4)C18—C191.396 (5)
O5—H5O0.8400C18—H180.9500
O6—C201.374 (4)C19—C201.402 (4)
O6—H6O0.8400C19—C251.532 (5)
C1—C21.535 (4)C21—C231.519 (6)
C1—H11.0000C21—C241.531 (5)
C2—C31.523 (4)C21—C221.536 (5)
C2—H21.0000C22—H22A0.9800
C3—C41.515 (4)C22—H22B0.9800
C3—H31.0000C22—H22C0.9800
C4—C51.522 (4)C23—H23A0.9800
C4—H41.0000C23—H23B0.9800
C5—C61.508 (4)C23—H23C0.9800
C5—H51.0000C24—H24A0.9800
C6—H6A0.9900C24—H24B0.9800
C6—H6B0.9900C24—H24C0.9800
C7—C81.509 (5)C25—C271.528 (5)
C7—H7A0.9900C25—C261.538 (5)
C7—H7B0.9900C25—C281.546 (5)
C8—C91.384 (5)C26—H26A0.9800
C8—C131.392 (5)C26—H26B0.9800
C9—C101.383 (5)C26—H26C0.9800
C9—H90.9500C27—H27A0.9800
C10—C111.377 (6)C27—H27B0.9800
C10—H100.9500C27—H27C0.9800
C11—C121.372 (6)C28—H28A0.9800
C11—H110.9500C28—H28B0.9800
C12—C131.387 (5)C28—H28C0.9800
C2—N—C14114.9 (3)C15—C14—H14A109.4
C2—N—H1N112 (3)N—C14—H14B109.4
C14—N—H1N110 (3)C15—C14—H14B109.4
C1—O1—C5113.5 (2)H14A—C14—H14B108.0
C1—O2—C7114.2 (3)C16—C15—C20119.3 (3)
C3—O3—H3O109.5C16—C15—C14120.0 (3)
C4—O4—H4O109.5C20—C15—C14120.6 (3)
C6—O5—H5O109.5C17—C16—C15121.8 (3)
C20—O6—H6O109.5C17—C16—H16119.1
O2—C1—O1112.9 (2)C15—C16—H16119.1
O2—C1—C2108.2 (3)C16—C17—C18117.3 (3)
O1—C1—C2110.4 (2)C16—C17—C21119.7 (3)
O2—C1—H1108.4C18—C17—C21123.0 (3)
O1—C1—H1108.4C17—C18—C19123.5 (3)
C2—C1—H1108.4C17—C18—H18118.2
N—C2—C3109.5 (3)C19—C18—H18118.2
N—C2—C1111.6 (2)C18—C19—C20117.2 (3)
C3—C2—C1111.0 (2)C18—C19—C25121.5 (3)
N—C2—H2108.2C20—C19—C25121.3 (3)
C3—C2—H2108.2O6—C20—C15119.2 (3)
C1—C2—H2108.2O6—C20—C19119.9 (3)
O3—C3—C4112.3 (2)C15—C20—C19120.9 (3)
O3—C3—C2107.2 (2)C23—C21—C24108.0 (3)
C4—C3—C2110.0 (3)C23—C21—C22111.3 (4)
O3—C3—H3109.1C24—C21—C22106.9 (3)
C4—C3—H3109.1C23—C21—C17108.6 (3)
C2—C3—H3109.1C24—C21—C17112.4 (3)
O4—C4—C3109.4 (2)C22—C21—C17109.7 (3)
O4—C4—C5109.4 (2)C21—C22—H22A109.5
C3—C4—C5108.5 (2)C21—C22—H22B109.5
O4—C4—H4109.8H22A—C22—H22B109.5
C3—C4—H4109.8C21—C22—H22C109.5
C5—C4—H4109.8H22A—C22—H22C109.5
O1—C5—C6107.0 (3)H22B—C22—H22C109.5
O1—C5—C4108.1 (2)C21—C23—H23A109.5
C6—C5—C4114.8 (3)C21—C23—H23B109.5
O1—C5—H5108.9H23A—C23—H23B109.5
C6—C5—H5108.9C21—C23—H23C109.5
C4—C5—H5108.9H23A—C23—H23C109.5
O5—C6—C5111.5 (3)H23B—C23—H23C109.5
O5—C6—H6A109.3C21—C24—H24A109.5
C5—C6—H6A109.3C21—C24—H24B109.5
O5—C6—H6B109.3H24A—C24—H24B109.5
C5—C6—H6B109.3C21—C24—H24C109.5
H6A—C6—H6B108.0H24A—C24—H24C109.5
O2—C7—C8112.7 (3)H24B—C24—H24C109.5
O2—C7—H7A109.0C27—C25—C19111.5 (3)
C8—C7—H7A109.0C27—C25—C26107.2 (3)
O2—C7—H7B109.0C19—C25—C26112.2 (3)
C8—C7—H7B109.0C27—C25—C28110.3 (3)
H7A—C7—H7B107.8C19—C25—C28108.5 (3)
C9—C8—C13118.7 (3)C26—C25—C28107.0 (3)
C9—C8—C7120.0 (3)C25—C26—H26A109.5
C13—C8—C7121.3 (3)C25—C26—H26B109.5
C10—C9—C8120.8 (4)H26A—C26—H26B109.5
C10—C9—H9119.6C25—C26—H26C109.5
C8—C9—H9119.6H26A—C26—H26C109.5
C11—C10—C9120.1 (4)H26B—C26—H26C109.5
C11—C10—H10119.9C25—C27—H27A109.5
C9—C10—H10119.9C25—C27—H27B109.5
C12—C11—C10119.8 (4)H27A—C27—H27B109.5
C12—C11—H11120.1C25—C27—H27C109.5
C10—C11—H11120.1H27A—C27—H27C109.5
C11—C12—C13120.4 (4)H27B—C27—H27C109.5
C11—C12—H12119.8C25—C28—H28A109.5
C13—C12—H12119.8C25—C28—H28B109.5
C12—C13—C8120.2 (3)H28A—C28—H28B109.5
C12—C13—H13119.9C25—C28—H28C109.5
C8—C13—H13119.9H28A—C28—H28C109.5
N—C14—C15111.0 (3)H28B—C28—H28C109.5
N—C14—H14A109.4
 

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