1,7,8-Tri-O-acetyl-6-O-benzoyl­castanospermine

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.

Computing details

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)

Crystal data

C21H25NO8	Dx = 1.327 Mg m^−3
Mr = 419.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 6.004 (2) Å	θ = 17–33°
b = 7.675 (4) Å	µ = 0.10 mm^−1
c = 45.564 (3) Å	T = 143 K
V = 2099.6 (13) Å^3	Needle, translucent colourless
Z = 4	0.75 × 0.25 × 0.20 mm
F(000) = 888

Data collection

Siemens R3m/scintillation counter diffractometer	θmax = 24.7°, θmin = 2.7°
Radiation source: fine-focus sealed tube	h = 0→7
Graphite monochromator	k = 0→8
ω scans	l = 0→53
2219 measured reflections	3 standard reflections every 97 reflections
2219 independent reflections	intensity decay: none
1373 reflections with I > 3σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.13	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.511P] where P = (Fo^2 + 2Fc^2)/3
1373 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O10	0.1167 (6)	0.5961 (5)	0.20477 (7)	0.0284 (10)
O11	0.2389 (6)	0.5870 (5)	0.07320 (7)	0.0288 (10)
O12	0.4438 (6)	0.3518 (5)	0.11144 (7)	0.0272 (9)
O13	0.1699 (6)	0.2579 (5)	0.16161 (7)	0.0262 (9)
O14	−0.0652 (8)	0.5406 (7)	0.24655 (9)	0.0591 (15)
O15	0.2830 (7)	0.1104 (6)	0.09314 (10)	0.0499 (13)
O16	0.5724 (6)	0.7226 (5)	0.07155 (8)	0.0329 (10)
O17	0.5180 (6)	0.2615 (6)	0.17990 (9)	0.0461 (12)
C1	−0.0866 (9)	0.5591 (8)	0.18847 (11)	0.0259 (13)
H1	−0.1663	0.4563	0.1969	0.031*
C2	−0.2380 (9)	0.7171 (7)	0.18719 (11)	0.0316 (15)
H2A	−0.1961	0.8031	0.2024	0.038*
H2B	−0.3953	0.6828	0.1902	0.038*
C3	−0.2042 (9)	0.7951 (8)	0.15577 (11)	0.0328 (15)
H3A	−0.3352	0.7717	0.1432	0.039*
H3B	−0.1789	0.9224	0.1567	0.039*
N4	−0.0084 (8)	0.7053 (6)	0.14485 (9)	0.0263 (12)
C5	0.0118 (9)	0.7044 (7)	0.11233 (11)	0.0296 (14)
H5A	0.0156	0.8251	0.1047	0.036*
H5B	−0.1167	0.6433	0.1034	0.036*
C6	0.2267 (9)	0.6105 (7)	0.10487 (10)	0.0260 (14)
H6	0.3579	0.6785	0.1121	0.031*
C7	0.2291 (9)	0.4278 (7)	0.11763 (11)	0.0272 (14)
H7	0.1097	0.3563	0.1082	0.033*
C8	0.1918 (9)	0.4328 (7)	0.15070 (11)	0.0237 (13)
H8	0.3185	0.4934	0.1606	0.028*
C9	−0.0230 (9)	0.5269 (7)	0.15667 (11)	0.0236 (13)
H9	−0.1475	0.4639	0.1466	0.028*
C10	0.1029 (10)	0.5830 (9)	0.23422 (11)	0.0341 (16)
C11	0.3172 (10)	0.6302 (9)	0.24865 (11)	0.0403 (17)
H11A	0.2981	0.6283	0.2700	0.061*
H11B	0.3623	0.7472	0.2424	0.061*
H11C	0.4323	0.5460	0.2430	0.061*
C12	0.4303 (9)	0.6345 (7)	0.05987 (11)	0.0266 (13)
C13	0.4479 (9)	0.5664 (7)	0.02936 (11)	0.0248 (13)
C14	0.6427 (9)	0.6026 (7)	0.01377 (12)	0.0312 (15)
H14	0.7567	0.6707	0.0226	0.037*
C15	0.6704 (10)	0.5396 (7)	−0.01440 (12)	0.0338 (15)
H15	0.8040	0.5631	−0.0249	0.041*
C16	0.5028 (10)	0.4421 (7)	−0.02740 (11)	0.0319 (15)
H16	0.5208	0.4003	−0.0469	0.038*
C17	0.3088 (10)	0.4055 (8)	−0.01202 (11)	0.0320 (14)
H17	0.1941	0.3387	−0.0209	0.038*
C18	0.2830 (9)	0.4666 (7)	0.01640 (11)	0.0300 (14)
H18	0.1514	0.4398	0.0271	0.036*
C19	0.4479 (10)	0.1905 (8)	0.09896 (12)	0.0319 (15)
C20	0.6814 (9)	0.1353 (8)	0.09378 (12)	0.0356 (16)
H20A	0.6832	0.0156	0.0863	0.053*
H20B	0.7648	0.1408	0.1122	0.053*
H20C	0.7506	0.2131	0.0794	0.053*
C21	0.3438 (11)	0.1881 (8)	0.17651 (11)	0.0306 (15)
C22	0.2891 (10)	0.0101 (7)	0.18698 (12)	0.0337 (15)
H22A	0.4204	−0.0413	0.1964	0.051*
H22B	0.2443	−0.0623	0.1703	0.051*
H22C	0.1667	0.0163	0.2012	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O10	0.028 (2)	0.042 (3)	0.0160 (18)	−0.004 (2)	0.0004 (17)	0.0020 (19)
O11	0.028 (2)	0.041 (2)	0.0177 (19)	−0.004 (2)	0.0009 (17)	−0.0006 (19)
O12	0.025 (2)	0.027 (2)	0.030 (2)	0.0035 (19)	−0.0022 (18)	−0.0063 (19)
O13	0.022 (2)	0.028 (2)	0.029 (2)	−0.002 (2)	−0.0058 (18)	0.0000 (18)
O14	0.052 (3)	0.098 (4)	0.027 (2)	−0.024 (3)	0.008 (2)	0.002 (3)
O15	0.033 (3)	0.044 (3)	0.072 (3)	−0.003 (3)	−0.001 (2)	−0.022 (3)
O16	0.030 (2)	0.039 (3)	0.029 (2)	−0.009 (2)	−0.0017 (19)	−0.004 (2)
O17	0.030 (2)	0.051 (3)	0.057 (3)	−0.004 (3)	−0.016 (2)	0.019 (3)
C1	0.022 (3)	0.033 (3)	0.022 (3)	−0.003 (3)	0.001 (3)	−0.001 (3)
C2	0.025 (3)	0.042 (4)	0.028 (3)	0.001 (3)	0.005 (3)	−0.005 (3)
C3	0.029 (3)	0.042 (4)	0.027 (3)	0.012 (3)	−0.002 (3)	−0.004 (3)
N4	0.029 (3)	0.029 (3)	0.021 (2)	0.003 (3)	0.000 (2)	−0.001 (2)
C5	0.033 (4)	0.035 (3)	0.021 (3)	0.001 (3)	−0.003 (3)	−0.001 (3)
C6	0.029 (3)	0.030 (4)	0.019 (3)	−0.010 (3)	−0.004 (3)	−0.003 (3)
C7	0.022 (3)	0.029 (3)	0.031 (3)	−0.003 (3)	0.000 (2)	−0.005 (3)
C8	0.026 (3)	0.020 (3)	0.026 (3)	0.001 (3)	−0.003 (3)	−0.001 (3)
C9	0.018 (3)	0.028 (3)	0.025 (3)	−0.001 (3)	0.000 (2)	−0.005 (3)
C10	0.034 (4)	0.043 (4)	0.025 (3)	−0.001 (4)	0.003 (3)	0.000 (3)
C11	0.039 (4)	0.056 (5)	0.025 (3)	−0.004 (4)	−0.005 (3)	−0.001 (3)
C12	0.025 (3)	0.029 (3)	0.025 (3)	0.005 (3)	0.002 (3)	0.003 (3)
C13	0.027 (3)	0.023 (3)	0.025 (3)	0.003 (3)	−0.005 (3)	0.002 (3)
C14	0.029 (3)	0.028 (4)	0.037 (3)	−0.002 (3)	−0.002 (3)	0.000 (3)
C15	0.032 (3)	0.035 (4)	0.035 (3)	0.004 (3)	0.004 (3)	0.006 (3)
C16	0.038 (3)	0.037 (4)	0.021 (3)	0.004 (4)	0.003 (3)	−0.003 (3)
C17	0.034 (3)	0.042 (4)	0.020 (3)	−0.002 (4)	−0.006 (3)	−0.002 (3)
C18	0.021 (3)	0.039 (4)	0.030 (3)	−0.005 (3)	−0.002 (3)	0.000 (3)
C19	0.026 (4)	0.040 (4)	0.030 (3)	−0.008 (3)	−0.005 (3)	−0.001 (3)
C20	0.028 (3)	0.038 (4)	0.040 (4)	0.000 (3)	0.007 (3)	−0.006 (3)
C21	0.032 (4)	0.037 (4)	0.022 (3)	0.000 (3)	−0.002 (3)	0.001 (3)
C22	0.042 (4)	0.029 (3)	0.030 (3)	0.005 (3)	−0.003 (3)	0.001 (3)

Geometric parameters (Å, º)

O10—C10	1.348 (6)	C7—H7	1.0000
O10—C1	1.457 (6)	C8—C9	1.503 (7)
O11—C12	1.350 (6)	C8—H8	1.0000
O11—C6	1.456 (6)	C9—H9	1.0000
O12—C19	1.363 (7)	C10—C11	1.490 (8)
O12—C7	1.442 (6)	C11—H11A	0.9800
O13—C21	1.356 (6)	C11—H11B	0.9800
O13—C8	1.437 (6)	C11—H11C	0.9800
O14—C10	1.200 (6)	C12—C13	1.489 (7)
O15—C19	1.195 (6)	C13—C18	1.384 (7)
O16—C12	1.212 (6)	C13—C14	1.396 (7)
O17—C21	1.198 (7)	C14—C15	1.382 (7)
C1—C2	1.517 (7)	C14—H14	0.9500
C1—C9	1.519 (7)	C15—C16	1.387 (7)
C1—H1	1.0000	C15—H15	0.9500
C2—C3	1.565 (7)	C16—C17	1.388 (8)
C2—H2A	0.9900	C16—H16	0.9500
C2—H2B	0.9900	C17—C18	1.386 (7)
C3—N4	1.451 (7)	C17—H17	0.9500
C3—H3A	0.9900	C18—H18	0.9500
C3—H3B	0.9900	C19—C20	1.483 (8)
N4—C9	1.475 (7)	C20—H20A	0.9800
N4—C5	1.486 (6)	C20—H20B	0.9800
C5—C6	1.516 (7)	C20—H20C	0.9800
C5—H5A	0.9900	C21—C22	1.484 (8)
C5—H5B	0.9900	C22—H22A	0.9800
C6—C7	1.518 (7)	C22—H22B	0.9800
C6—H6	1.0000	C22—H22C	0.9800
C7—C8	1.524 (7)
C10—O10—C1	116.2 (4)	N4—C9—H9	109.1
C12—O11—C6	117.1 (4)	C8—C9—H9	109.1
C19—O12—C7	117.7 (4)	C1—C9—H9	109.1
C21—O13—C8	118.1 (4)	O14—C10—O10	122.6 (5)
O10—C1—C2	111.5 (4)	O14—C10—C11	125.9 (5)
O10—C1—C9	107.9 (4)	O10—C10—C11	111.6 (5)
C2—C1—C9	104.1 (4)	C10—C11—H11A	109.5
O10—C1—H1	111.0	C10—C11—H11B	109.5
C2—C1—H1	111.0	H11A—C11—H11B	109.5
C9—C1—H1	111.0	C10—C11—H11C	109.5
C1—C2—C3	105.3 (4)	H11A—C11—H11C	109.5
C1—C2—H2A	110.7	H11B—C11—H11C	109.5
C3—C2—H2A	110.7	O16—C12—O11	123.5 (5)
C1—C2—H2B	110.7	O16—C12—C13	123.8 (5)
C3—C2—H2B	110.7	O11—C12—C13	112.7 (5)
H2A—C2—H2B	108.8	C18—C13—C14	119.5 (5)
N4—C3—C2	103.7 (4)	C18—C13—C12	122.8 (5)
N4—C3—H3A	111.0	C14—C13—C12	117.7 (5)
C2—C3—H3A	111.0	C15—C14—C13	120.3 (5)
N4—C3—H3B	111.0	C15—C14—H14	119.9
C2—C3—H3B	111.0	C13—C14—H14	119.9
H3A—C3—H3B	109.0	C14—C15—C16	119.9 (5)
C3—N4—C9	105.5 (4)	C14—C15—H15	120.1
C3—N4—C5	114.2 (4)	C16—C15—H15	120.1
C9—N4—C5	111.4 (4)	C15—C16—C17	120.2 (5)
N4—C5—C6	107.2 (4)	C15—C16—H16	119.9
N4—C5—H5A	110.3	C17—C16—H16	119.9
C6—C5—H5A	110.3	C18—C17—C16	119.8 (5)
N4—C5—H5B	110.3	C18—C17—H17	120.1
C6—C5—H5B	110.3	C16—C17—H17	120.1
H5A—C5—H5B	108.5	C13—C18—C17	120.4 (5)
O11—C6—C5	108.9 (4)	C13—C18—H18	119.8
O11—C6—C7	105.3 (4)	C17—C18—H18	119.8
C5—C6—C7	111.2 (5)	O15—C19—O12	123.0 (6)
O11—C6—H6	110.4	O15—C19—C20	126.9 (6)
C5—C6—H6	110.4	O12—C19—C20	110.1 (5)
C7—C6—H6	110.4	C19—C20—H20A	109.5
O12—C7—C6	107.9 (4)	C19—C20—H20B	109.5
O12—C7—C8	109.6 (4)	H20A—C20—H20B	109.5
C6—C7—C8	110.7 (4)	C19—C20—H20C	109.5
O12—C7—H7	109.6	H20A—C20—H20C	109.5
C6—C7—H7	109.6	H20B—C20—H20C	109.5
C8—C7—H7	109.6	O17—C21—O13	123.4 (5)
O13—C8—C9	107.9 (4)	O17—C21—C22	125.8 (6)
O13—C8—C7	109.4 (4)	O13—C21—C22	110.8 (5)
C9—C8—C7	108.5 (4)	C21—C22—H22A	109.5
O13—C8—H8	110.3	C21—C22—H22B	109.5
C9—C8—H8	110.3	H22A—C22—H22B	109.5
C7—C8—H8	110.3	C21—C22—H22C	109.5
N4—C9—C8	109.2 (5)	H22A—C22—H22C	109.5
N4—C9—C1	102.2 (4)	H22B—C22—H22C	109.5
C8—C9—C1	117.8 (4)
C10—O10—C1—C2	83.1 (6)	O13—C8—C9—N4	−178.2 (4)
C10—O10—C1—C9	−163.2 (5)	C7—C8—C9—N4	−59.8 (5)
O10—C1—C2—C3	102.0 (5)	O13—C8—C9—C1	65.9 (6)
C9—C1—C2—C3	−14.1 (5)	C7—C8—C9—C1	−175.7 (5)
C1—C2—C3—N4	−12.6 (5)	O10—C1—C9—N4	−83.2 (5)
C2—C3—N4—C9	35.7 (5)	C2—C1—C9—N4	35.4 (5)
C2—C3—N4—C5	158.3 (5)	O10—C1—C9—C8	36.5 (7)
C3—N4—C5—C6	178.5 (4)	C2—C1—C9—C8	155.0 (5)
C9—N4—C5—C6	−62.1 (6)	C1—O10—C10—O14	1.2 (10)
C12—O11—C6—C5	130.7 (5)	C1—O10—C10—C11	−177.8 (5)
C12—O11—C6—C7	−110.0 (5)	C6—O11—C12—O16	−13.9 (8)
N4—C5—C6—O11	172.8 (4)	C6—O11—C12—C13	165.9 (4)
N4—C5—C6—C7	57.2 (6)	O16—C12—C13—C18	−179.7 (5)
C19—O12—C7—C6	−129.6 (5)	O11—C12—C13—C18	0.5 (7)
C19—O12—C7—C8	109.8 (5)	O16—C12—C13—C14	1.9 (8)
O11—C6—C7—O12	66.2 (5)	O11—C12—C13—C14	−177.9 (5)
C5—C6—C7—O12	−176.0 (4)	C18—C13—C14—C15	0.2 (8)
O11—C6—C7—C8	−173.9 (4)	C12—C13—C14—C15	178.7 (5)
C5—C6—C7—C8	−56.1 (6)	C13—C14—C15—C16	0.9 (8)
C21—O13—C8—C9	−137.1 (5)	C14—C15—C16—C17	−1.0 (9)
C21—O13—C8—C7	105.0 (5)	C15—C16—C17—C18	0.0 (9)
O12—C7—C8—O13	−67.6 (5)	C14—C13—C18—C17	−1.2 (8)
C6—C7—C8—O13	173.6 (4)	C12—C13—C18—C17	−179.6 (5)
O12—C7—C8—C9	174.9 (4)	C16—C17—C18—C13	1.1 (8)
C6—C7—C8—C9	56.1 (6)	C7—O12—C19—O15	−0.3 (8)
C3—N4—C9—C8	−170.6 (4)	C7—O12—C19—C20	179.0 (5)
C5—N4—C9—C8	64.9 (6)	C8—O13—C21—O17	−3.5 (8)
C3—N4—C9—C1	−45.1 (5)	C8—O13—C21—C22	178.0 (4)
C5—N4—C9—C1	−169.5 (4)