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The crystal structure of the title compound, C24H28O8, has been determined. The conformation of the furan­ose ring can be described as 58% ideal envelope OE conformer and 42% ideal twisted OT1 conformer. The 1,3-dioxane ring adopts a chair conformation with the anhydro-O atom pointing upwards. Both phenyl rings are quasi-perpendicular to the mean plane of the furan­ose ring. The hydrogen bonding is intermolecular and consists of infinite chains parallel to the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008702/gs1095sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008702/gs1095Isup2.hkl
Contains datablock I

CCDC reference: 150869

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: maXus (Mackay et al., 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: maXus.

1,6-Anhydro-2,3-di-O-benzyl-5 C-[(R)-ethoxycarbonyl(hydroxy)methyl]-L– altrofuranose top
Crystal data top
C24H28O8Dx = 1.326 Mg m3
Mr = 444.46Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 5.6740 (14) Åθ = 9.5–32.9°
b = 11.699 (6) ŵ = 0.83 mm1
c = 33.5340 (15) ÅT = 293 K
V = 2226.0 (13) Å3Prismatic, colourless
Z = 40.40 × 0.25 × 0.25 mm
F(000) = 944
Data collection top
Enraf-Nonius MACH3
diffractometer
Rint = 0.000
Radiation source: Nonius FR591 rotating Cu anodeθmax = 70.0°, θmin = 2.6°
Graphite monochromatorh = 06
ω/2θ scansk = 014
2447 measured reflectionsl = 040
2447 independent reflections3 standard reflections every 60 min
1942 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0816P)2 + 0.5716P]
where P = (Fo2 + 2Fc2)/3
2447 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

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
O10.7901 (6)0.6073 (3)0.14208 (8)0.0920 (9)
C10.8302 (7)0.7212 (5)0.15612 (12)0.0890 (14)
H110.94080.71990.17850.116*
C20.6094 (6)0.7855 (3)0.16776 (10)0.0680 (9)
H210.65280.84900.18540.088*
C30.5215 (6)0.8341 (3)0.12800 (10)0.0622 (8)
H310.37620.79520.11980.081*
C40.7208 (6)0.8046 (4)0.09952 (11)0.0729 (10)
H410.74750.86660.08040.095*
O40.9225 (5)0.7889 (3)0.12487 (9)0.1065 (12)
C50.6807 (6)0.6893 (4)0.07783 (10)0.0683 (10)
C60.6254 (8)0.6006 (3)0.10985 (10)0.0758 (10)
H610.46720.61320.11990.099*
H620.63100.52480.09820.099*
O50.8922 (5)0.6571 (4)0.05771 (8)0.1104 (13)
H50.88510.67750.03430.144*
C70.4882 (6)0.7014 (3)0.04625 (11)0.0644 (8)
H710.33520.71420.05900.084*
O70.5486 (5)0.7962 (2)0.02231 (8)0.0848 (9)
H70.42820.82950.01530.110*
C80.4785 (6)0.5947 (3)0.02018 (11)0.0686 (9)
O80.5528 (6)0.5882 (3)0.01323 (9)0.0946 (9)
O90.3750 (5)0.5093 (2)0.03964 (8)0.0810 (8)
C90.3541 (12)0.4011 (4)0.01875 (15)0.1029 (16)
H910.48430.39220.00030.134*
H920.35960.33850.03770.134*
C100.1332 (16)0.3987 (5)0.0027 (2)0.137 (2)
H100.11820.32710.01650.178*
H10B0.12970.46010.02170.178*
H10C0.00510.40720.01570.178*
O30.4794 (6)0.9548 (2)0.13268 (8)0.0820 (8)
C110.3235 (8)0.9966 (3)0.10342 (11)0.0782 (11)
H11B0.17730.95380.10430.102*
H11C0.39270.98700.07720.102*
C120.2748 (7)1.1203 (3)0.11076 (10)0.0654 (9)
C130.4263 (9)1.1911 (3)0.13033 (12)0.0808 (11)
H130.56911.16220.13950.105*
C140.3731 (11)1.3047 (4)0.13690 (15)0.0984 (15)
H140.48141.35100.15000.128*
C150.1682 (11)1.3490 (4)0.12474 (15)0.0977 (15)
H150.13091.42490.13020.127*
C160.0142 (10)1.2812 (4)0.10417 (16)0.1049 (15)
H160.12631.31180.09470.136*
C170.0661 (9)1.1671 (4)0.09742 (15)0.0925 (13)
H170.04101.12160.08370.120*
O20.4317 (4)0.7205 (2)0.18621 (6)0.0656 (6)
C180.4966 (9)0.6844 (4)0.22553 (11)0.0931 (13)
H180.51880.75040.24260.121*
H18B0.64330.64190.22460.121*
C190.3039 (7)0.6103 (3)0.24169 (9)0.0672 (9)
C200.2348 (13)0.5154 (4)0.22282 (15)0.1144 (18)
H200.30850.49560.19900.149*
C210.0636 (19)0.4479 (6)0.2369 (2)0.159 (3)
H21B0.02020.38310.22260.207*
C220.0458 (13)0.4717 (7)0.2710 (2)0.136 (3)
H220.16140.42280.28080.177*
C230.0108 (14)0.5649 (8)0.29078 (16)0.140 (3)
H230.06730.58290.31430.181*
C240.1905 (12)0.6378 (5)0.27625 (12)0.1084 (17)
H240.23090.70370.29010.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0818 (19)0.118 (2)0.0761 (15)0.0400 (19)0.0012 (15)0.0385 (16)
C10.055 (2)0.137 (4)0.075 (2)0.011 (3)0.0155 (18)0.045 (3)
C20.0616 (19)0.077 (2)0.0649 (17)0.0138 (19)0.0178 (16)0.0123 (17)
C30.0604 (19)0.0586 (17)0.0676 (18)0.0135 (17)0.0193 (16)0.0143 (15)
C40.0461 (17)0.099 (3)0.0737 (19)0.0198 (19)0.0174 (16)0.035 (2)
O40.0492 (13)0.182 (3)0.0878 (17)0.0314 (19)0.0206 (13)0.063 (2)
C50.0404 (15)0.099 (3)0.0660 (18)0.0145 (18)0.0056 (14)0.0297 (19)
C60.083 (3)0.075 (2)0.0689 (19)0.025 (2)0.008 (2)0.0194 (17)
O50.0619 (15)0.200 (4)0.0690 (15)0.047 (2)0.0153 (13)0.042 (2)
C70.0513 (17)0.0682 (18)0.074 (2)0.0036 (17)0.0021 (16)0.0171 (16)
O70.0921 (19)0.0736 (14)0.0887 (16)0.0150 (15)0.0386 (16)0.0318 (13)
C80.0559 (19)0.0687 (19)0.081 (2)0.0126 (17)0.0129 (18)0.0184 (17)
O80.106 (2)0.0917 (18)0.0866 (17)0.0068 (19)0.0311 (18)0.0105 (15)
O90.0897 (19)0.0704 (14)0.0827 (15)0.0150 (15)0.0141 (15)0.0085 (13)
C90.138 (5)0.064 (2)0.106 (3)0.000 (3)0.014 (4)0.004 (2)
C100.171 (6)0.092 (3)0.147 (5)0.020 (4)0.030 (5)0.015 (3)
O30.102 (2)0.0600 (12)0.0844 (15)0.0180 (15)0.0386 (16)0.0104 (11)
C110.098 (3)0.0642 (19)0.073 (2)0.010 (2)0.027 (2)0.0056 (16)
C120.075 (2)0.0596 (18)0.0618 (17)0.0117 (19)0.0039 (18)0.0049 (15)
C130.086 (3)0.069 (2)0.088 (2)0.001 (2)0.005 (2)0.0082 (19)
C140.117 (4)0.070 (2)0.108 (3)0.001 (3)0.007 (3)0.025 (2)
C150.113 (4)0.072 (2)0.108 (3)0.008 (3)0.019 (3)0.005 (2)
C160.100 (4)0.082 (3)0.133 (4)0.009 (3)0.004 (3)0.023 (3)
C170.091 (3)0.078 (2)0.109 (3)0.014 (3)0.017 (3)0.015 (2)
O20.0633 (13)0.0786 (14)0.0550 (11)0.0068 (13)0.0066 (10)0.0148 (10)
C180.101 (3)0.115 (3)0.0631 (19)0.026 (3)0.019 (2)0.026 (2)
C190.076 (2)0.076 (2)0.0487 (15)0.010 (2)0.0028 (16)0.0111 (15)
C200.153 (5)0.094 (3)0.095 (3)0.027 (4)0.026 (4)0.021 (3)
C210.208 (9)0.128 (5)0.143 (5)0.068 (6)0.001 (6)0.023 (4)
C220.101 (4)0.178 (7)0.130 (5)0.024 (5)0.013 (4)0.097 (5)
C230.135 (6)0.208 (7)0.076 (3)0.046 (6)0.044 (4)0.037 (4)
C240.156 (5)0.108 (3)0.061 (2)0.018 (4)0.013 (3)0.000 (2)
Geometric parameters (Å, º) top
O1—C11.431 (6)C9—C101.446 (10)
O1—C61.431 (5)O3—C111.409 (4)
C1—O41.414 (5)C11—C121.493 (5)
C1—C21.512 (6)C12—C131.363 (5)
C2—O21.406 (4)C12—C171.379 (6)
C2—C31.533 (4)C13—C141.380 (6)
C3—O31.441 (4)C14—C151.337 (8)
C3—C41.520 (6)C15—C161.367 (7)
C4—O41.438 (4)C16—C171.385 (7)
C4—C51.549 (6)O2—C181.433 (4)
C5—O51.427 (4)C18—C191.497 (6)
C5—C61.526 (5)C19—C201.337 (6)
C5—C71.528 (5)C19—C241.364 (6)
C7—O71.411 (4)C20—C211.338 (10)
C7—C81.525 (5)C21—C221.332 (10)
C8—O81.199 (4)C22—C231.315 (9)
C8—O91.330 (4)C23—C241.416 (10)
O9—C91.452 (5)
C1—O1—C6113.8 (3)O8—C8—C7125.1 (3)
O4—C1—O1109.7 (4)O9—C8—C7110.5 (3)
O4—C1—C2102.7 (4)C8—O9—C9117.0 (3)
O1—C1—C2114.6 (3)C10—C9—O9109.2 (5)
O2—C2—C1116.0 (3)C11—O3—C3111.7 (3)
O2—C2—C3110.5 (3)O3—C11—C12109.8 (3)
C1—C2—C3103.3 (3)C13—C12—C17117.1 (4)
O3—C3—C4114.4 (3)C13—C12—C11123.5 (4)
O3—C3—C2108.8 (3)C17—C12—C11119.4 (4)
C4—C3—C2102.7 (3)C12—C13—C14121.6 (5)
O4—C4—C3104.5 (3)C15—C14—C13121.0 (5)
O4—C4—C5106.4 (3)C14—C15—C16119.0 (5)
C3—C4—C5112.5 (3)C15—C16—C17120.4 (5)
C1—O4—C4102.4 (3)C12—C17—C16120.8 (5)
O5—C5—C6109.0 (3)C2—O2—C18112.4 (3)
O5—C5—C7107.3 (3)O2—C18—C19108.4 (3)
C6—C5—C7113.8 (3)C20—C19—C24117.4 (5)
O5—C5—C4109.2 (3)C20—C19—C18121.6 (4)
C6—C5—C4107.0 (3)C24—C19—C18121.0 (4)
C7—C5—C4110.5 (3)C19—C20—C21122.4 (6)
O1—C6—C5111.1 (3)C22—C21—C20121.2 (7)
O7—C7—C8109.0 (3)C23—C22—C21119.5 (6)
O7—C7—C5107.1 (3)C22—C23—C24120.1 (5)
C8—C7—C5110.3 (3)C19—C24—C23119.3 (5)
O8—C8—O9124.5 (4)
C6—O1—C1—O460.6 (4)O7—C7—C8—O812.9 (5)
C6—O1—C1—C254.2 (4)C5—C7—C8—O8104.4 (4)
O4—C1—C2—O2155.5 (3)O7—C7—C8—O9166.9 (3)
O1—C1—C2—O236.7 (4)C5—C7—C8—O975.8 (4)
O4—C1—C2—C334.6 (4)O8—C8—O9—C90.6 (6)
O1—C1—C2—C384.3 (3)C7—C8—O9—C9179.5 (4)
O2—C2—C3—O3106.4 (3)C8—O9—C9—C1090.2 (6)
C1—C2—C3—O3128.9 (3)C4—C3—O3—C1187.0 (4)
O2—C2—C3—C4131.9 (3)C2—C3—O3—C11158.8 (3)
C1—C2—C3—C47.3 (4)C3—O3—C11—C12176.9 (3)
O3—C3—C4—O495.8 (3)O3—C11—C12—C1325.8 (5)
C2—C3—C4—O421.9 (4)O3—C11—C12—C17154.0 (4)
O3—C3—C4—C5149.1 (3)C17—C12—C13—C140.6 (6)
C2—C3—C4—C593.1 (3)C11—C12—C13—C14179.2 (4)
O1—C1—O4—C472.7 (4)C12—C13—C14—C151.0 (8)
C2—C1—O4—C449.6 (4)C13—C14—C15—C162.5 (8)
C3—C4—O4—C145.0 (4)C14—C15—C16—C172.5 (8)
C5—C4—O4—C174.2 (4)C13—C12—C17—C160.6 (7)
O4—C4—C5—O555.2 (3)C11—C12—C17—C16179.2 (4)
C3—C4—C5—O5169.1 (3)C15—C16—C17—C120.9 (8)
O4—C4—C5—C662.6 (3)C1—C2—O2—C1869.7 (4)
C3—C4—C5—C651.2 (3)C3—C2—O2—C18173.3 (3)
O4—C4—C5—C7173.0 (2)C2—O2—C18—C19176.6 (3)
C3—C4—C5—C773.1 (3)O2—C18—C19—C2057.7 (6)
C1—O1—C6—C547.3 (4)O2—C18—C19—C24121.8 (4)
O5—C5—C6—O170.5 (4)C24—C19—C20—C210.8 (9)
C7—C5—C6—O1169.8 (3)C18—C19—C20—C21179.7 (6)
C4—C5—C6—O147.5 (4)C19—C20—C21—C220.7 (12)
O5—C5—C7—O767.3 (4)C20—C21—C22—C231.8 (12)
C6—C5—C7—O7172.0 (3)C21—C22—C23—C241.4 (11)
C4—C5—C7—O751.7 (4)C20—C19—C24—C231.1 (8)
O5—C5—C7—C851.2 (4)C18—C19—C24—C23179.3 (5)
C6—C5—C7—C869.5 (4)C22—C23—C24—C190.1 (9)
C4—C5—C7—C8170.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O7i0.822.142.879 (3)150.5
O7—H7···O8ii0.822.343.136 (5)164.2
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x1/2, y+3/2, z.
 

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