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The title compound (alternatively 1,7,8-tri­acetoxy­per­hydro­indolizin-6-yl benzoate), C21H25NO8, was obtained during studies of castanospermine derivatives. The crystal structure consists of independent mol­ecules with only van der Waals contacts. The fused six- and five-membered rings adopt chair and twist conformations, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010477/qa0363sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010477/qa0363Isup2.hkl
Contains datablock I

CCDC reference: 150733

Computing details top

Data collection: R3m Software (Siemens, 1983); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SHELXS85 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C21H25NO8Dx = 1.327 Mg m3
Mr = 419.42Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 6.004 (2) Åθ = 17–33°
b = 7.675 (4) ŵ = 0.10 mm1
c = 45.564 (3) ÅT = 143 K
V = 2099.6 (13) Å3Needle, translucent colourless
Z = 40.75 × 0.25 × 0.20 mm
F(000) = 888
Data collection top
Siemens R3m/scintillation counter
diffractometer
θmax = 24.7°, θmin = 2.7°
Radiation source: fine-focus sealed tubeh = 07
Graphite monochromatork = 08
ω scansl = 053
2219 measured reflections3 standard reflections every 97 reflections
2219 independent reflections intensity decay: none
1373 reflections with I > 3σ(I)
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.13Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + (0.0405P)2 + 0.511P]
where P = (Fo2 + 2Fc2)/3
1373 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.17 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 for observed reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O100.1167 (6)0.5961 (5)0.20477 (7)0.0284 (10)
O110.2389 (6)0.5870 (5)0.07320 (7)0.0288 (10)
O120.4438 (6)0.3518 (5)0.11144 (7)0.0272 (9)
O130.1699 (6)0.2579 (5)0.16161 (7)0.0262 (9)
O140.0652 (8)0.5406 (7)0.24655 (9)0.0591 (15)
O150.2830 (7)0.1104 (6)0.09314 (10)0.0499 (13)
O160.5724 (6)0.7226 (5)0.07155 (8)0.0329 (10)
O170.5180 (6)0.2615 (6)0.17990 (9)0.0461 (12)
C10.0866 (9)0.5591 (8)0.18847 (11)0.0259 (13)
H10.16630.45630.19690.031*
C20.2380 (9)0.7171 (7)0.18719 (11)0.0316 (15)
H2A0.19610.80310.20240.038*
H2B0.39530.68280.19020.038*
C30.2042 (9)0.7951 (8)0.15577 (11)0.0328 (15)
H3A0.33520.77170.14320.039*
H3B0.17890.92240.15670.039*
N40.0084 (8)0.7053 (6)0.14485 (9)0.0263 (12)
C50.0118 (9)0.7044 (7)0.11233 (11)0.0296 (14)
H5A0.01560.82510.10470.036*
H5B0.11670.64330.10340.036*
C60.2267 (9)0.6105 (7)0.10487 (10)0.0260 (14)
H60.35790.67850.11210.031*
C70.2291 (9)0.4278 (7)0.11763 (11)0.0272 (14)
H70.10970.35630.10820.033*
C80.1918 (9)0.4328 (7)0.15070 (11)0.0237 (13)
H80.31850.49340.16060.028*
C90.0230 (9)0.5269 (7)0.15667 (11)0.0236 (13)
H90.14750.46390.14660.028*
C100.1029 (10)0.5830 (9)0.23422 (11)0.0341 (16)
C110.3172 (10)0.6302 (9)0.24865 (11)0.0403 (17)
H11A0.29810.62830.27000.061*
H11B0.36230.74720.24240.061*
H11C0.43230.54600.24300.061*
C120.4303 (9)0.6345 (7)0.05987 (11)0.0266 (13)
C130.4479 (9)0.5664 (7)0.02936 (11)0.0248 (13)
C140.6427 (9)0.6026 (7)0.01377 (12)0.0312 (15)
H140.75670.67070.02260.037*
C150.6704 (10)0.5396 (7)0.01440 (12)0.0338 (15)
H150.80400.56310.02490.041*
C160.5028 (10)0.4421 (7)0.02740 (11)0.0319 (15)
H160.52080.40030.04690.038*
C170.3088 (10)0.4055 (8)0.01202 (11)0.0320 (14)
H170.19410.33870.02090.038*
C180.2830 (9)0.4666 (7)0.01640 (11)0.0300 (14)
H180.15140.43980.02710.036*
C190.4479 (10)0.1905 (8)0.09896 (12)0.0319 (15)
C200.6814 (9)0.1353 (8)0.09378 (12)0.0356 (16)
H20A0.68320.01560.08630.053*
H20B0.76480.14080.11220.053*
H20C0.75060.21310.07940.053*
C210.3438 (11)0.1881 (8)0.17651 (11)0.0306 (15)
C220.2891 (10)0.0101 (7)0.18698 (12)0.0337 (15)
H22A0.42040.04130.19640.051*
H22B0.24430.06230.17030.051*
H22C0.16670.01630.20120.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O100.028 (2)0.042 (3)0.0160 (18)0.004 (2)0.0004 (17)0.0020 (19)
O110.028 (2)0.041 (2)0.0177 (19)0.004 (2)0.0009 (17)0.0006 (19)
O120.025 (2)0.027 (2)0.030 (2)0.0035 (19)0.0022 (18)0.0063 (19)
O130.022 (2)0.028 (2)0.029 (2)0.002 (2)0.0058 (18)0.0000 (18)
O140.052 (3)0.098 (4)0.027 (2)0.024 (3)0.008 (2)0.002 (3)
O150.033 (3)0.044 (3)0.072 (3)0.003 (3)0.001 (2)0.022 (3)
O160.030 (2)0.039 (3)0.029 (2)0.009 (2)0.0017 (19)0.004 (2)
O170.030 (2)0.051 (3)0.057 (3)0.004 (3)0.016 (2)0.019 (3)
C10.022 (3)0.033 (3)0.022 (3)0.003 (3)0.001 (3)0.001 (3)
C20.025 (3)0.042 (4)0.028 (3)0.001 (3)0.005 (3)0.005 (3)
C30.029 (3)0.042 (4)0.027 (3)0.012 (3)0.002 (3)0.004 (3)
N40.029 (3)0.029 (3)0.021 (2)0.003 (3)0.000 (2)0.001 (2)
C50.033 (4)0.035 (3)0.021 (3)0.001 (3)0.003 (3)0.001 (3)
C60.029 (3)0.030 (4)0.019 (3)0.010 (3)0.004 (3)0.003 (3)
C70.022 (3)0.029 (3)0.031 (3)0.003 (3)0.000 (2)0.005 (3)
C80.026 (3)0.020 (3)0.026 (3)0.001 (3)0.003 (3)0.001 (3)
C90.018 (3)0.028 (3)0.025 (3)0.001 (3)0.000 (2)0.005 (3)
C100.034 (4)0.043 (4)0.025 (3)0.001 (4)0.003 (3)0.000 (3)
C110.039 (4)0.056 (5)0.025 (3)0.004 (4)0.005 (3)0.001 (3)
C120.025 (3)0.029 (3)0.025 (3)0.005 (3)0.002 (3)0.003 (3)
C130.027 (3)0.023 (3)0.025 (3)0.003 (3)0.005 (3)0.002 (3)
C140.029 (3)0.028 (4)0.037 (3)0.002 (3)0.002 (3)0.000 (3)
C150.032 (3)0.035 (4)0.035 (3)0.004 (3)0.004 (3)0.006 (3)
C160.038 (3)0.037 (4)0.021 (3)0.004 (4)0.003 (3)0.003 (3)
C170.034 (3)0.042 (4)0.020 (3)0.002 (4)0.006 (3)0.002 (3)
C180.021 (3)0.039 (4)0.030 (3)0.005 (3)0.002 (3)0.000 (3)
C190.026 (4)0.040 (4)0.030 (3)0.008 (3)0.005 (3)0.001 (3)
C200.028 (3)0.038 (4)0.040 (4)0.000 (3)0.007 (3)0.006 (3)
C210.032 (4)0.037 (4)0.022 (3)0.000 (3)0.002 (3)0.001 (3)
C220.042 (4)0.029 (3)0.030 (3)0.005 (3)0.003 (3)0.001 (3)
Geometric parameters (Å, º) top
O10—C101.348 (6)C7—H71.0000
O10—C11.457 (6)C8—C91.503 (7)
O11—C121.350 (6)C8—H81.0000
O11—C61.456 (6)C9—H91.0000
O12—C191.363 (7)C10—C111.490 (8)
O12—C71.442 (6)C11—H11A0.9800
O13—C211.356 (6)C11—H11B0.9800
O13—C81.437 (6)C11—H11C0.9800
O14—C101.200 (6)C12—C131.489 (7)
O15—C191.195 (6)C13—C181.384 (7)
O16—C121.212 (6)C13—C141.396 (7)
O17—C211.198 (7)C14—C151.382 (7)
C1—C21.517 (7)C14—H140.9500
C1—C91.519 (7)C15—C161.387 (7)
C1—H11.0000C15—H150.9500
C2—C31.565 (7)C16—C171.388 (8)
C2—H2A0.9900C16—H160.9500
C2—H2B0.9900C17—C181.386 (7)
C3—N41.451 (7)C17—H170.9500
C3—H3A0.9900C18—H180.9500
C3—H3B0.9900C19—C201.483 (8)
N4—C91.475 (7)C20—H20A0.9800
N4—C51.486 (6)C20—H20B0.9800
C5—C61.516 (7)C20—H20C0.9800
C5—H5A0.9900C21—C221.484 (8)
C5—H5B0.9900C22—H22A0.9800
C6—C71.518 (7)C22—H22B0.9800
C6—H61.0000C22—H22C0.9800
C7—C81.524 (7)
C10—O10—C1116.2 (4)N4—C9—H9109.1
C12—O11—C6117.1 (4)C8—C9—H9109.1
C19—O12—C7117.7 (4)C1—C9—H9109.1
C21—O13—C8118.1 (4)O14—C10—O10122.6 (5)
O10—C1—C2111.5 (4)O14—C10—C11125.9 (5)
O10—C1—C9107.9 (4)O10—C10—C11111.6 (5)
C2—C1—C9104.1 (4)C10—C11—H11A109.5
O10—C1—H1111.0C10—C11—H11B109.5
C2—C1—H1111.0H11A—C11—H11B109.5
C9—C1—H1111.0C10—C11—H11C109.5
C1—C2—C3105.3 (4)H11A—C11—H11C109.5
C1—C2—H2A110.7H11B—C11—H11C109.5
C3—C2—H2A110.7O16—C12—O11123.5 (5)
C1—C2—H2B110.7O16—C12—C13123.8 (5)
C3—C2—H2B110.7O11—C12—C13112.7 (5)
H2A—C2—H2B108.8C18—C13—C14119.5 (5)
N4—C3—C2103.7 (4)C18—C13—C12122.8 (5)
N4—C3—H3A111.0C14—C13—C12117.7 (5)
C2—C3—H3A111.0C15—C14—C13120.3 (5)
N4—C3—H3B111.0C15—C14—H14119.9
C2—C3—H3B111.0C13—C14—H14119.9
H3A—C3—H3B109.0C14—C15—C16119.9 (5)
C3—N4—C9105.5 (4)C14—C15—H15120.1
C3—N4—C5114.2 (4)C16—C15—H15120.1
C9—N4—C5111.4 (4)C15—C16—C17120.2 (5)
N4—C5—C6107.2 (4)C15—C16—H16119.9
N4—C5—H5A110.3C17—C16—H16119.9
C6—C5—H5A110.3C18—C17—C16119.8 (5)
N4—C5—H5B110.3C18—C17—H17120.1
C6—C5—H5B110.3C16—C17—H17120.1
H5A—C5—H5B108.5C13—C18—C17120.4 (5)
O11—C6—C5108.9 (4)C13—C18—H18119.8
O11—C6—C7105.3 (4)C17—C18—H18119.8
C5—C6—C7111.2 (5)O15—C19—O12123.0 (6)
O11—C6—H6110.4O15—C19—C20126.9 (6)
C5—C6—H6110.4O12—C19—C20110.1 (5)
C7—C6—H6110.4C19—C20—H20A109.5
O12—C7—C6107.9 (4)C19—C20—H20B109.5
O12—C7—C8109.6 (4)H20A—C20—H20B109.5
C6—C7—C8110.7 (4)C19—C20—H20C109.5
O12—C7—H7109.6H20A—C20—H20C109.5
C6—C7—H7109.6H20B—C20—H20C109.5
C8—C7—H7109.6O17—C21—O13123.4 (5)
O13—C8—C9107.9 (4)O17—C21—C22125.8 (6)
O13—C8—C7109.4 (4)O13—C21—C22110.8 (5)
C9—C8—C7108.5 (4)C21—C22—H22A109.5
O13—C8—H8110.3C21—C22—H22B109.5
C9—C8—H8110.3H22A—C22—H22B109.5
C7—C8—H8110.3C21—C22—H22C109.5
N4—C9—C8109.2 (5)H22A—C22—H22C109.5
N4—C9—C1102.2 (4)H22B—C22—H22C109.5
C8—C9—C1117.8 (4)
C10—O10—C1—C283.1 (6)O13—C8—C9—N4178.2 (4)
C10—O10—C1—C9163.2 (5)C7—C8—C9—N459.8 (5)
O10—C1—C2—C3102.0 (5)O13—C8—C9—C165.9 (6)
C9—C1—C2—C314.1 (5)C7—C8—C9—C1175.7 (5)
C1—C2—C3—N412.6 (5)O10—C1—C9—N483.2 (5)
C2—C3—N4—C935.7 (5)C2—C1—C9—N435.4 (5)
C2—C3—N4—C5158.3 (5)O10—C1—C9—C836.5 (7)
C3—N4—C5—C6178.5 (4)C2—C1—C9—C8155.0 (5)
C9—N4—C5—C662.1 (6)C1—O10—C10—O141.2 (10)
C12—O11—C6—C5130.7 (5)C1—O10—C10—C11177.8 (5)
C12—O11—C6—C7110.0 (5)C6—O11—C12—O1613.9 (8)
N4—C5—C6—O11172.8 (4)C6—O11—C12—C13165.9 (4)
N4—C5—C6—C757.2 (6)O16—C12—C13—C18179.7 (5)
C19—O12—C7—C6129.6 (5)O11—C12—C13—C180.5 (7)
C19—O12—C7—C8109.8 (5)O16—C12—C13—C141.9 (8)
O11—C6—C7—O1266.2 (5)O11—C12—C13—C14177.9 (5)
C5—C6—C7—O12176.0 (4)C18—C13—C14—C150.2 (8)
O11—C6—C7—C8173.9 (4)C12—C13—C14—C15178.7 (5)
C5—C6—C7—C856.1 (6)C13—C14—C15—C160.9 (8)
C21—O13—C8—C9137.1 (5)C14—C15—C16—C171.0 (9)
C21—O13—C8—C7105.0 (5)C15—C16—C17—C180.0 (9)
O12—C7—C8—O1367.6 (5)C14—C13—C18—C171.2 (8)
C6—C7—C8—O13173.6 (4)C12—C13—C18—C17179.6 (5)
O12—C7—C8—C9174.9 (4)C16—C17—C18—C131.1 (8)
C6—C7—C8—C956.1 (6)C7—O12—C19—O150.3 (8)
C3—N4—C9—C8170.6 (4)C7—O12—C19—C20179.0 (5)
C5—N4—C9—C864.9 (6)C8—O13—C21—O173.5 (8)
C3—N4—C9—C145.1 (5)C8—O13—C21—C22178.0 (4)
C5—N4—C9—C1169.5 (4)
 

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