The relative configuration of the title compound, C23H29NO11, prepared in a synthetic study on the natural product sphingofungin E, has been determined. The six-membered ring adopts a chair form and the five substituents are all axial.
Supporting information
CCDC reference: 145660
The title compound was synthesized from D-glucose. The crystals were grown from a toluene solution.
There are two possible conformations of the methoxymethyloxy group. The site-occupation factors of O7—C12—O8—C13 and O7—C14—O8—C15 were assumed to be 65 and 35%, respectively. The C14 and C15 atoms were refined isotropically. The positional parameters of all the H atoms were calculated geometrically and fixed with U(H) = 1.2Ueq(parent atom). The absolute structure was assigned based on the known absolute configurations around the C2, C3 and C4 atoms, which came from D-glucose.
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
C23H29NO11 | Dx = 1.297 Mg m−3 |
Mr = 495.48 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 25 reflections |
Hall symbol: P 43 | θ = 10–15° |
a = 14.381 (2) Å | µ = 0.10 mm−1 |
c = 12.265 (2) Å | T = 296 K |
V = 2536.4 (7) Å3 | Prism, colourless |
Z = 4 | 0.5 × 0.5 × 0.5 mm |
Data collection top
Rigaku AFC-5S diffractometer | θmax = 26° |
θ–2θ scans | h = 0→18 |
2844 measured reflections | k = 0→18 |
2621 independent reflections | l = 0→15 |
1656 reflections with I > 2σ(I) | 3 standard reflections every 100 reflections |
Rint = 0.010 | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + {0.05(Fo2 + 2Fc2)/3}2] |
wR(F2) = 0.116 | (Δ/σ)max = 0.026 |
S = 1.19 | Δρmax = 0.16 e Å−3 |
2621 reflections | Δρmin = −0.14 e Å−3 |
324 parameters | Absolute structure: see text, no Friedel pair |
Crystal data top
C23H29NO11 | Z = 4 |
Mr = 495.48 | Mo Kα radiation |
Tetragonal, P43 | µ = 0.10 mm−1 |
a = 14.381 (2) Å | T = 296 K |
c = 12.265 (2) Å | 0.5 × 0.5 × 0.5 mm |
V = 2536.4 (7) Å3 | |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.010 |
2844 measured reflections | 3 standard reflections every 100 reflections |
2621 independent reflections | intensity decay: none |
1656 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters not refined |
wR(F2) = 0.116 | Δρmax = 0.16 e Å−3 |
S = 1.19 | Δρmin = −0.14 e Å−3 |
2621 reflections | Absolute structure: see text, no Friedel pair |
324 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.8376 (2) | 0.0426 (2) | 0.1522 (9) | 0.0708 (8) | |
O2 | 0.6961 (2) | −0.0126 (2) | 0.1098 (9) | 0.095 (1) | |
O3 | 0.6033 (2) | 0.0822 (2) | 0.3845 (9) | 0.0616 (8) | |
O4 | 0.5143 (5) | −0.0318 (4) | 0.3257 (10) | 0.176 (2) | |
O5 | 0.5844 (2) | 0.2293 (2) | 0.1511 (9) | 0.0685 (8) | |
O6 | 0.4895 (3) | 0.3465 (3) | 0.1936 (9) | 0.139 (2) | |
O7 | 0.6760 (2) | 0.2902 (2) | 0.4182 (9) | 0.0676 (8) | |
O8 | 0.6565 (4) | 0.4513 (2) | 0.4194 (9) | 0.126 (2) | |
O9 | 0.7898 (2) | 0.2565 (2) | 0.1565 (9) | 0.0544 (6) | |
O10 | 0.8245 (3) | 0.4067 (2) | 0.1749 (9) | 0.095 (1) | |
O11 | 0.8208 (2) | 0.0282 (2) | 0.4279 (9) | 0.0715 (8) | |
N1 | 0.7183 (2) | 0.0905 (2) | 0.2499 (9) | 0.0481 (7) | |
C1 | 0.6233 (2) | 0.1108 (2) | 0.2744 (9) | 0.0521 (8) | |
C2 | 0.6025 (3) | 0.2138 (3) | 0.2661 (9) | 0.0565 (9) | |
C3 | 0.6802 (3) | 0.2800 (2) | 0.3030 (9) | 0.0519 (8) | |
C4 | 0.7780 (2) | 0.2474 (2) | 0.2730 (9) | 0.0485 (8) | |
C5 | 0.7948 (2) | 0.1443 (2) | 0.2961 (9) | 0.0467 (8) | |
C6 | 0.8773 (3) | 0.1035 (3) | 0.2323 (9) | 0.058 (1) | |
C7 | 0.7445 (3) | 0.0357 (3) | 0.1654 (9) | 0.0625 (10) | |
C8 | 0.5483 (3) | 0.0086 (3) | 0.3992 (10) | 0.087 (1) | |
C9 | 0.5325 (4) | −0.0080 (4) | 0.518 (1) | 0.108 (2) | |
C10 | 0.5245 (4) | 0.2988 (4) | 0.126 (1) | 0.099 (2) | |
C11 | 0.5122 (6) | 0.3063 (5) | 0.006 (1) | 0.148 (3) | |
C12 | 0.6184 (6) | 0.3661 (5) | 0.452 (1) | 0.094 (2) | 0.65 |
C13 | 0.746 (1) | 0.4666 (9) | 0.459 (2) | 0.179 (5) | 0.65 |
C14 | 0.716 (1) | 0.383 (1) | 0.456 (2) | 0.091 (4)* | 0.35 |
C15 | 0.569 (2) | 0.439 (2) | 0.472 (2) | 0.160 (8)* | 0.35 |
C16 | 0.8177 (3) | 0.3398 (3) | 0.1179 (9) | 0.066 (1) | |
C17 | 0.8383 (4) | 0.3356 (3) | −0.0004 (10) | 0.098 (2) | |
C18 | 0.8061 (3) | 0.1253 (2) | 0.4178 (9) | 0.0544 (9) | |
C19 | 0.8250 (3) | −0.0041 (3) | 0.5345 (9) | 0.069 (1) | |
C20 | 0.8342 (3) | −0.1084 (3) | 0.5332 (9) | 0.062 (1) | |
C21 | 0.7859 (3) | −0.1620 (3) | 0.4599 (9) | 0.072 (1) | |
C22 | 0.7954 (4) | −0.2575 (3) | 0.4611 (10) | 0.094 (2) | |
C23 | 0.8545 (4) | −0.2981 (3) | 0.537 (1) | 0.100 (2) | |
C24 | 0.9010 (4) | −0.2459 (4) | 0.6098 (10) | 0.104 (2) | |
C25 | 0.8917 (3) | −0.1516 (3) | 0.6072 (10) | 0.080 (1) | |
H1 | 0.5837 | 0.0773 | 0.2250 | 0.0626* | |
H2 | 0.5472 | 0.2273 | 0.3069 | 0.0678* | |
H3 | 0.6698 | 0.3397 | 0.2702 | 0.0623* | |
H4 | 0.8234 | 0.2844 | 0.3105 | 0.0582* | |
H5 | 0.9119 | 0.1523 | 0.1975 | 0.0691* | |
H6 | 0.9176 | 0.0695 | 0.2803 | 0.0691* | |
H7 | 0.5909 | −0.0195 | 0.5534 | 0.1290* | |
H8 | 0.4927 | −0.0611 | 0.5273 | 0.1290* | |
H9 | 0.5036 | 0.0456 | 0.5499 | 0.1290* | |
H10 | 0.5713 | 0.3188 | −0.0278 | 0.1792* | |
H11 | 0.4879 | 0.2487 | −0.0221 | 0.1792* | |
H12 | 0.4698 | 0.3558 | −0.0106 | 0.1792* | |
H13 | 0.6136 | 0.3653 | 0.5306 | 0.1132* | 0.65 |
H14 | 0.5578 | 0.3591 | 0.4210 | 0.1132* | 0.65 |
H15 | 0.7455 | 0.4651 | 0.5379 | 0.2150* | 0.65 |
H16 | 0.7687 | 0.5259 | 0.4353 | 0.2150* | 0.65 |
H17 | 0.7873 | 0.4185 | 0.4332 | 0.2150* | 0.65 |
H18 | 0.7768 | 0.3908 | 0.4254 | 0.1094* | 0.35 |
H19 | 0.7197 | 0.3834 | 0.5339 | 0.1094* | 0.35 |
H20 | 0.5773 | 0.4444 | 0.5488 | 0.1899* | 0.35 |
H21 | 0.5441 | 0.3802 | 0.4531 | 0.1899* | 0.35 |
H22 | 0.5276 | 0.4878 | 0.4471 | 0.1899* | 0.35 |
H23 | 0.8577 | 0.3958 | −0.0253 | 0.1175* | |
H24 | 0.8872 | 0.2914 | −0.0131 | 0.1175* | |
H25 | 0.7835 | 0.3167 | −0.0392 | 0.1175* | |
H26 | 0.7510 | 0.1434 | 0.4566 | 0.0652* | |
H27 | 0.8585 | 0.1589 | 0.4461 | 0.0652* | |
H28 | 0.7692 | 0.0130 | 0.5725 | 0.0830* | |
H29 | 0.8778 | 0.0227 | 0.5707 | 0.0830* | |
H30 | 0.7454 | −0.1330 | 0.4077 | 0.0864* | |
H31 | 0.7619 | −0.2954 | 0.4102 | 0.1132* | |
H32 | 0.8622 | −0.3644 | 0.5379 | 0.1207* | |
H33 | 0.9403 | −0.2748 | 0.6633 | 0.1243* | |
H34 | 0.9261 | −0.1145 | 0.6582 | 0.0955* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.072 (1) | 0.069 (2) | 0.071 (2) | 0.013 (1) | 0.009 (1) | −0.022 (1) |
O2 | 0.101 (2) | 0.080 (2) | 0.105 (3) | −0.004 (2) | −0.019 (2) | −0.054 (2) |
O3 | 0.053 (1) | 0.071 (2) | 0.061 (1) | −0.010 (1) | 0.006 (1) | 0.010 (1) |
O4 | 0.235 (6) | 0.170 (5) | 0.125 (4) | −0.156 (4) | 0.023 (4) | −0.023 (3) |
O5 | 0.068 (2) | 0.072 (2) | 0.066 (2) | −0.005 (1) | −0.012 (1) | 0.010 (1) |
O6 | 0.133 (4) | 0.113 (3) | 0.171 (5) | 0.066 (3) | −0.024 (3) | 0.016 (3) |
O7 | 0.094 (2) | 0.057 (2) | 0.051 (1) | 0.006 (1) | 0.006 (2) | −0.008 (1) |
O8 | 0.199 (5) | 0.063 (2) | 0.116 (3) | 0.018 (2) | 0.016 (3) | −0.016 (2) |
O9 | 0.070 (2) | 0.042 (1) | 0.051 (1) | −0.008 (1) | 0.009 (1) | 0.000 (1) |
O10 | 0.157 (3) | 0.047 (2) | 0.082 (2) | −0.029 (2) | 0.004 (2) | 0.006 (1) |
O11 | 0.105 (2) | 0.053 (1) | 0.057 (1) | 0.011 (1) | 0.001 (2) | 0.008 (1) |
N1 | 0.050 (1) | 0.042 (2) | 0.052 (2) | −0.003 (1) | 0.002 (1) | −0.003 (1) |
C1 | 0.045 (1) | 0.056 (2) | 0.055 (2) | −0.010 (1) | −0.003 (2) | 0.000 (2) |
C2 | 0.048 (2) | 0.059 (2) | 0.062 (2) | 0.005 (1) | 0.004 (2) | 0.003 (2) |
C3 | 0.065 (2) | 0.043 (2) | 0.048 (2) | 0.006 (1) | 0.004 (2) | 0.000 (2) |
C4 | 0.057 (2) | 0.040 (1) | 0.048 (1) | −0.006 (1) | 0.000 (2) | −0.004 (2) |
C5 | 0.048 (2) | 0.039 (1) | 0.053 (2) | −0.005 (1) | 0.001 (1) | 0.001 (2) |
C6 | 0.053 (2) | 0.052 (2) | 0.068 (2) | 0.003 (2) | 0.011 (2) | 0.004 (2) |
C7 | 0.074 (2) | 0.047 (2) | 0.066 (2) | 0.009 (2) | 0.006 (2) | −0.010 (2) |
C8 | 0.072 (3) | 0.077 (3) | 0.112 (3) | −0.018 (2) | 0.030 (3) | 0.030 (3) |
C9 | 0.096 (4) | 0.111 (4) | 0.115 (4) | −0.006 (3) | 0.032 (3) | 0.049 (4) |
C10 | 0.083 (3) | 0.076 (3) | 0.138 (4) | −0.008 (2) | −0.040 (3) | 0.047 (3) |
C11 | 0.167 (6) | 0.136 (5) | 0.142 (4) | −0.040 (5) | −0.085 (6) | 0.067 (5) |
C12 | 0.112 (6) | 0.080 (3) | 0.091 (6) | 0.035 (3) | 0.032 (5) | −0.021 (4) |
C13 | 0.222 (9) | 0.15 (1) | 0.16 (1) | −0.09 (1) | −0.013 (10) | −0.056 (9) |
C16 | 0.081 (3) | 0.045 (2) | 0.074 (2) | −0.003 (2) | 0.009 (2) | 0.010 (1) |
C17 | 0.147 (5) | 0.072 (3) | 0.075 (2) | 0.005 (3) | 0.027 (3) | 0.014 (3) |
C18 | 0.057 (2) | 0.052 (1) | 0.055 (2) | −0.003 (2) | −0.004 (2) | 0.002 (2) |
C19 | 0.084 (3) | 0.067 (2) | 0.056 (2) | 0.007 (2) | −0.008 (2) | 0.009 (2) |
C20 | 0.056 (2) | 0.067 (2) | 0.062 (2) | 0.003 (2) | 0.005 (2) | 0.014 (2) |
C21 | 0.082 (3) | 0.068 (2) | 0.066 (3) | 0.002 (2) | −0.005 (2) | 0.012 (2) |
C22 | 0.118 (4) | 0.068 (2) | 0.097 (4) | −0.009 (3) | 0.004 (3) | 0.004 (3) |
C23 | 0.120 (4) | 0.065 (3) | 0.116 (4) | 0.013 (3) | 0.015 (3) | 0.030 (3) |
C24 | 0.108 (4) | 0.092 (2) | 0.111 (5) | 0.025 (3) | −0.012 (3) | 0.034 (3) |
C25 | 0.068 (3) | 0.087 (2) | 0.084 (3) | 0.013 (2) | −0.018 (2) | 0.020 (3) |
Geometric parameters (Å, º) top
O1—C6 | 1.436 (5) | C9—H8 | 0.961 |
O1—C7 | 1.352 (5) | C9—H9 | 0.960 |
O2—C7 | 1.197 (6) | C10—C11 | 1.49 (1) |
O3—C1 | 1.441 (5) | C11—H10 | 0.961 |
O3—C8 | 1.333 (6) | C11—H11 | 0.961 |
O4—C8 | 1.178 (8) | C11—H12 | 0.957 |
O5—C2 | 1.452 (5) | C12—H13 | 0.962 |
O5—C10 | 1.355 (6) | C12—H14 | 0.957 |
O6—C10 | 1.187 (9) | C13—H15 | 0.962 |
O7—C3 | 1.422 (5) | C13—H16 | 0.959 |
O7—C12 | 1.432 (8) | C13—H17 | 0.967 |
O7—C14 | 1.52 (2) | C14—H18 | 0.959 |
O8—C12 | 1.40 (1) | C14—H19 | 0.961 |
O8—C13 | 1.40 (2) | C15—H20 | 0.953 |
O8—C14 | 1.38 (2) | C15—H21 | 0.952 |
O8—C15 | 1.42 (3) | C15—H22 | 0.967 |
O9—C4 | 1.445 (5) | C16—C17 | 1.482 (7) |
O9—C16 | 1.349 (5) | C17—H23 | 0.960 |
O10—C16 | 1.192 (5) | C17—H24 | 0.961 |
O11—C18 | 1.418 (5) | C17—H25 | 0.959 |
O11—C19 | 1.389 (5) | C18—H26 | 0.960 |
N1—C1 | 1.429 (5) | C18—H27 | 0.960 |
N1—C5 | 1.459 (5) | C19—C20 | 1.505 (6) |
N1—C7 | 1.354 (5) | C19—H28 | 0.960 |
C1—C2 | 1.515 (6) | C19—H29 | 0.960 |
C1—H1 | 0.960 | C20—C21 | 1.373 (7) |
C2—C3 | 1.535 (6) | C20—C25 | 1.375 (6) |
C2—H2 | 0.960 | C21—C22 | 1.381 (7) |
C3—C4 | 1.527 (5) | C21—H30 | 0.960 |
C3—H3 | 0.960 | C22—C23 | 1.391 (9) |
C4—C5 | 1.529 (5) | C22—H31 | 0.960 |
C4—H4 | 0.960 | C23—C24 | 1.343 (9) |
C5—C6 | 1.537 (6) | C23—H32 | 0.960 |
C5—C18 | 1.526 (6) | C24—C25 | 1.362 (7) |
C6—H5 | 0.960 | C24—H33 | 0.961 |
C6—H6 | 0.960 | C25—H34 | 0.960 |
C8—C9 | 1.496 (9) | H14—H21 | 0.534 |
C9—H7 | 0.959 | H17—H18 | 0.436 |
| | | |
O1···C6i | 3.271 (5) | O6···C15vi | 3.38 (3) |
O1···C18i | 3.447 (5) | O6···C11iv | 3.413 (9) |
O2···C4i | 3.296 (5) | O6···C17iv | 3.526 (9) |
O2···C9ii | 3.487 (7) | O8···C15vi | 3.26 (3) |
O2···C24iii | 3.561 (8) | O10···C8vi | 3.163 (6) |
O2···O10i | 3.580 (5) | O10···C9vi | 3.398 (7) |
O3···O10iv | 3.169 (4) | O10···C2vi | 3.469 (5) |
O4···C13i | 3.51 (2) | C15···C15vi | 3.59 (2) |
O4···C23v | 3.545 (7) | C15···C15iv | 3.59 (2) |
O4···O10iv | 3.572 (8) | | |
| | | |
C6—O1—C7 | 110.9 (3) | H10—C11—H11 | 109 |
C1—O3—C8 | 118.1 (4) | H10—C11—H12 | 109.6 |
C2—O5—C10 | 116.6 (4) | H11—C11—H12 | 109.6 |
C3—O7—C12 | 113.2 (5) | O7—C12—O8 | 110.8 (6) |
C3—O7—C14 | 112.1 (7) | O7—C12—H13 | 109.0 |
C12—O8—C13 | 113.4 (9) | O7—C12—H14 | 109.2 |
C14—O8—C15 | 108 (1) | O8—C12—H13 | 109.0 |
C4—O9—C16 | 117.6 (3) | O8—C12—H14 | 109.3 |
C18—O11—C19 | 114.7 (3) | H13—C12—H14 | 109 |
C1—N1—C5 | 122.0 (3) | O8—C13—H15 | 109 |
C1—N1—C7 | 123.1 (3) | O8—C13—H16 | 110 |
C5—N1—C7 | 113.3 (3) | O8—C13—H17 | 109 |
O3—C1—N1 | 109.2 (3) | H15—C13—H16 | 109 |
O3—C1—C2 | 107.6 (3) | H15—C13—H17 | 108 |
O3—C1—H1 | 109.3 | H16—C13—H17 | 108 |
N1—C1—C2 | 112.0 (3) | O7—C14—O8 | 107 (1) |
N1—C1—H1 | 109.3 | O7—C14—H18 | 109 |
C2—C1—H1 | 109.4 | O7—C14—H19 | 109 |
O5—C2—C1 | 104.5 (3) | O8—C14—H18 | 110 |
O5—C2—C3 | 108.8 (3) | O8—C14—H19 | 110 |
O5—C2—H2 | 109.0 | H18—C14—H19 | 109 |
C1—C2—C3 | 116.3 (3) | O8—C15—H20 | 109 |
C1—C2—H2 | 109.0 | O8—C15—H21 | 109 |
C3—C2—H2 | 109.0 | O8—C15—H22 | 108 |
O7—C3—C2 | 109.0 (3) | H20—C15—H21 | 110 |
O7—C3—C4 | 108.1 (3) | H20—C15—H22 | 109 |
O7—C3—H3 | 108.5 | H21—C15—H22 | 109 |
C2—C3—C4 | 114.1 (3) | O9—C16—O10 | 122.3 (4) |
C2—C3—H3 | 108.5 | O9—C16—C17 | 111.5 (4) |
C4—C3—H3 | 108.5 | O10—C16—C17 | 126.2 (4) |
O9—C4—C3 | 108.6 (3) | C16—C17—H23 | 109.5 |
O9—C4—C5 | 104.6 (3) | C16—C17—H24 | 109.4 |
O9—C4—H4 | 110.0 | C16—C17—H25 | 109.5 |
C3—C4—C5 | 113.5 (3) | H23—C17—H24 | 109.4 |
C3—C4—H4 | 110.0 | H23—C17—H25 | 109.6 |
C5—C4—H4 | 110.0 | H24—C17—H25 | 109.5 |
N1—C5—C4 | 108.9 (3) | O11—C18—C5 | 106.1 (3) |
N1—C5—C6 | 100.5 (3) | O11—C18—H26 | 110.3 |
N1—C5—C18 | 111.4 (3) | O11—C18—H27 | 110.3 |
C4—C5—C6 | 113.4 (3) | C5—C18—H26 | 110.3 |
C4—C5—C18 | 111.8 (3) | C5—C18—H27 | 110.3 |
C6—C5—C18 | 110.3 (3) | H26—C18—H27 | 109.4 |
O1—C6—C5 | 105.9 (3) | O11—C19—C20 | 109.1 (4) |
O1—C6—H5 | 110.4 | O11—C19—H28 | 109.6 |
O1—C6—H6 | 110.4 | O11—C19—H29 | 109.6 |
C5—C6—H5 | 110.4 | C20—C19—H28 | 109.6 |
C5—C6—H6 | 110.3 | C20—C19—H29 | 109.6 |
H5—C6—H6 | 109.5 | H28—C19—H29 | 109 |
O1—C7—O2 | 123.3 (4) | C19—C20—C21 | 121.4 (4) |
O1—C7—N1 | 109.0 (4) | C19—C20—C25 | 119.7 (4) |
O2—C7—N1 | 127.7 (4) | C21—C20—C25 | 118.8 (4) |
O3—C8—O4 | 122.3 (5) | C20—C21—C22 | 120.1 (5) |
O3—C8—C9 | 110.4 (6) | C20—C21—H30 | 120.0 |
O4—C8—C9 | 127.1 (5) | C22—C21—H30 | 119.9 |
C8—C9—H7 | 109.5 | C21—C22—C23 | 119.1 (6) |
C8—C9—H8 | 109 | C21—C22—H31 | 120.5 |
C8—C9—H9 | 109.5 | C23—C22—H31 | 120.4 |
H7—C9—H8 | 109.5 | C22—C23—C24 | 120.9 (5) |
H7—C9—H9 | 109 | C22—C23—H32 | 119.6 |
H8—C9—H9 | 109.4 | C24—C23—H32 | 119.6 |
O5—C10—O6 | 122.5 (6) | C23—C24—C25 | 119.5 (5) |
O5—C10—C11 | 110.7 (7) | C23—C24—H33 | 120.2 |
O6—C10—C11 | 126.8 (6) | C25—C24—H33 | 120.3 |
C10—C11—H10 | 109.4 | C20—C25—C24 | 121.6 (5) |
C10—C11—H11 | 109.4 | C20—C25—H34 | 119.2 |
C10—C11—H12 | 109 | C24—C25—H34 | 119.2 |
Symmetry codes: (i) −y+1, x−1, z−1/4; (ii) −x+1, −y, z−1/2; (iii) y+1, −x+1, z−3/4; (iv) y, −x+1, z+1/4; (v) −y, x−1, z−1/4; (vi) −y+1, x, z−1/4. |
Experimental details
Crystal data |
Chemical formula | C23H29NO11 |
Mr | 495.48 |
Crystal system, space group | Tetragonal, P43 |
Temperature (K) | 296 |
a, c (Å) | 14.381 (2), 12.265 (2) |
V (Å3) | 2536.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.5 × 0.5 × 0.5 |
|
Data collection |
Diffractometer | Rigaku AFC-5S diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2844, 2621, 1656 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.116, 1.19 |
No. of reflections | 2621 |
No. of parameters | 324 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Absolute structure | See text, no Friedel pair |
Selected bond lengths (Å) topO1—C6 | 1.436 (5) | O7—C3 | 1.422 (5) |
O1—C7 | 1.352 (5) | O9—C4 | 1.445 (5) |
O2—C7 | 1.197 (6) | N1—C1 | 1.429 (5) |
O3—C1 | 1.441 (5) | N1—C5 | 1.459 (5) |
O5—C2 | 1.452 (5) | N1—C7 | 1.354 (5) |
The title compound was synthesized in a synthetic study on sphingofungin E (Oishi et al., 2000). The stereochemistries at C-3, C-4 and C-5 (atom labels C2, C3 and C4, respectively) came from those at C-2, C-3 and C-4 of D-glucose, respectively.