rac-(2R*,3S*,5S*,6R*,7S*,8S*)-7,8-Dichloro-bicyclo-[2.2.2]octane-2,3,5,6-tetrayl tetra-acetate.

The title compound, C(16)H(20)Cl(2)O(8), contains a central bicyclo-[2.2.2]octane skeleton with slightly twisted conformation. In this structure, the C-C bond lengths are in the range 1.525 (2)-1.552 (2) Å. Two sides of this skeleton have cis,cis acet-oxy substituents and the Cl atoms have a trans arrangement. An extensive network of weak C-H⋯O interactions stabilizes the crystal structure.

Related literature

For background information on inositol and its derivatives, see: Michell (2008 ▶); Reitz (1991 ▶); Dwek (1996 ▶); Billington et al. (1994 ▶); Varki (1993 ▶); Heightman & Vasella (1991 ▶). For background on the carba-analogues of oligosaccharides, see: Ogawa et al. (2000 ▶, 1988 ▶); Saumi (1990 ▶); Saumi & Ogawa (1990 ▶). For related structures, see: Baran et al. (2008 ▶); Mehta et al. (2007 ▶); Shih et al. (2007 ▶); Gültekin et al. (2004 ▶); Mehta & Ramesh (2001 ▶); Balcı (1997 ▶); Balcı et al. (1990 ▶);Ülkü et al. (1995 ▶); Buser & Vasella (2006 ▶).

Experimental

Crystal data

C16H20Cl2O8

M = 411.22

Monoclinic,

a = 10.1061 (3) Å

b = 13.3383 (4) Å

c = 14.2229 (3) Å

β = 90.189 (2)°

V = 1917.21 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 294 K

0.5 × 0.3 × 0.2 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.873, T max = 0.927

54750 measured reflections

5628 independent reflections

5575 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.157

S = 1.32

5628 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900484X/kp2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900484X/kp2205Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H20Cl2O8	F(000) = 856
Mr = 411.22	Dx = 1.425 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 16740 reflections
a = 10.1061 (3) Å	θ = 2.9–30.0°
b = 13.3383 (4) Å	µ = 0.38 mm−1
c = 14.2229 (3) Å	T = 294 K
β = 90.189 (2)°	Block, colourless
V = 1917.21 (9) Å3	0.5 × 0.3 × 0.2 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	5628 independent reflections
graphite	5575 reflections with I > 2σ(I)
Detector resolution: 10 pixels mm-1	Rint = 0.024
dtprofit.ref scans	θmax = 30.2°, θmin = 2.9°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→14
Tmin = 0.873, Tmax = 0.927	k = −18→18
54750 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.32	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.7822P] where P = (Fo2 + 2Fc2)/3
5628 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	0.43075 (15)	0.68316 (10)	0.83281 (11)	0.0493 (3)
O2	0.40605 (14)	0.67994 (10)	0.65495 (10)	0.0456 (3)
O3	0.65280 (15)	0.43371 (11)	0.67091 (11)	0.0515 (4)
O4	0.61501 (15)	0.40594 (12)	0.84846 (12)	0.0562 (4)
O6	0.7006 (2)	0.27009 (13)	0.68650 (16)	0.0760 (6)
C1	0.4340 (2)	0.49728 (14)	0.64831 (14)	0.0432 (4)
H1	0.4388	0.4942	0.5796	0.052*
O7	0.5083 (2)	0.68542 (15)	0.51586 (12)	0.0707 (5)
C3	0.49349 (19)	0.59673 (14)	0.79258 (14)	0.0431 (4)
H3	0.5857	0.5931	0.8139	0.052*
O5	0.5382 (3)	0.2886 (2)	0.94322 (18)	0.1158 (11)
C9	0.7365 (2)	0.35432 (17)	0.67186 (17)	0.0565 (5)
C5	0.49031 (19)	0.41067 (14)	0.79928 (14)	0.0445 (4)
H5	0.4368	0.3518	0.8151	0.053*
C8	0.27942 (19)	0.50853 (14)	0.78399 (14)	0.0436 (4)
H8	0.2452	0.5772	0.7868	0.052*
C2	0.48878 (19)	0.59749 (13)	0.68357 (14)	0.0411 (4)
H2	0.5783	0.6073	0.6589	0.049*
C7	0.2918 (2)	0.47717 (15)	0.68102 (14)	0.0451 (4)
H7	0.2761	0.4048	0.6773	0.054*
C6	0.5167 (2)	0.41264 (14)	0.69188 (15)	0.0454 (4)
H6	0.4911	0.3483	0.6640	0.055*
C13	0.4288 (2)	0.71914 (16)	0.56923 (15)	0.0492 (4)
C4	0.41742 (19)	0.50589 (14)	0.82877 (14)	0.0420 (4)
H4	0.4103	0.5088	0.8974	0.050*
C14	0.4989 (2)	0.76967 (16)	0.82909 (17)	0.0551 (5)
C12	0.7623 (3)	0.3419 (3)	0.9605 (2)	0.0785 (8)
H12C	0.7600	0.3159	1.0234	0.118*
H12A	0.7942	0.4097	0.9617	0.118*
H12B	0.8202	0.3015	0.9229	0.118*
C15	0.4182 (3)	0.85465 (19)	0.8642 (2)	0.0736 (7)
H15A	0.4056	0.8478	0.9307	0.110*
H15B	0.3337	0.8546	0.8331	0.110*
H15C	0.4630	0.9166	0.8514	0.110*
C10	0.6262 (3)	0.3398 (2)	0.91940 (16)	0.0590 (5)
C11	0.8745 (3)	0.3867 (2)	0.6533 (2)	0.0790 (8)
H11C	0.9172	0.4033	0.7116	0.119*
H11A	0.8737	0.4444	0.6130	0.119*
H11B	0.9218	0.3332	0.6232	0.119*
C16	0.3424 (3)	0.8084 (2)	0.5524 (2)	0.0740 (8)
H16C	0.3678	0.8405	0.4948	0.111*
H16B	0.3521	0.8548	0.6036	0.111*
H16A	0.2518	0.7873	0.5481	0.111*
O8	0.60945 (19)	0.77413 (14)	0.79959 (18)	0.0809 (6)
Cl2	0.16803 (6)	0.42687 (5)	0.84582 (5)	0.06100 (17)
Cl1	0.16992 (6)	0.53836 (5)	0.60893 (5)	0.06395 (18)

	U11	U22	U33	U12	U13	U23
O1	0.0548 (8)	0.0384 (7)	0.0547 (8)	−0.0079 (6)	0.0039 (6)	−0.0063 (6)
O2	0.0461 (7)	0.0389 (7)	0.0519 (7)	0.0066 (5)	0.0045 (6)	0.0054 (5)
O3	0.0473 (8)	0.0395 (7)	0.0676 (9)	0.0078 (6)	0.0118 (7)	0.0062 (6)
O4	0.0438 (8)	0.0582 (9)	0.0665 (9)	0.0014 (6)	−0.0081 (7)	0.0147 (7)
O6	0.0746 (12)	0.0437 (9)	0.1097 (16)	0.0146 (8)	0.0097 (11)	0.0094 (9)
C1	0.0472 (10)	0.0381 (9)	0.0445 (9)	0.0027 (7)	0.0024 (7)	0.0014 (7)
O7	0.0774 (12)	0.0783 (12)	0.0564 (10)	0.0201 (10)	0.0151 (9)	0.0154 (9)
C3	0.0414 (9)	0.0386 (9)	0.0493 (10)	−0.0036 (7)	−0.0006 (7)	0.0007 (7)
O5	0.0850 (15)	0.163 (3)	0.0992 (17)	−0.0404 (16)	−0.0287 (12)	0.0788 (18)
C9	0.0581 (12)	0.0464 (11)	0.0650 (13)	0.0160 (9)	0.0092 (10)	0.0055 (10)
C5	0.0413 (9)	0.0396 (9)	0.0527 (10)	0.0002 (7)	−0.0017 (8)	0.0076 (8)
C8	0.0406 (9)	0.0368 (9)	0.0534 (10)	−0.0030 (7)	0.0038 (8)	0.0028 (7)
C2	0.0382 (8)	0.0356 (8)	0.0496 (10)	0.0026 (7)	0.0038 (7)	0.0056 (7)
C7	0.0446 (10)	0.0382 (9)	0.0525 (10)	−0.0019 (7)	−0.0041 (8)	−0.0013 (8)
C6	0.0449 (10)	0.0358 (9)	0.0556 (11)	0.0020 (7)	0.0042 (8)	0.0014 (8)
C13	0.0514 (11)	0.0437 (10)	0.0525 (11)	0.0014 (8)	−0.0026 (9)	0.0080 (8)
C4	0.0425 (9)	0.0396 (9)	0.0439 (9)	−0.0033 (7)	0.0010 (7)	0.0031 (7)
C14	0.0606 (13)	0.0411 (10)	0.0636 (13)	−0.0115 (9)	−0.0101 (10)	0.0013 (9)
C12	0.0621 (15)	0.104 (2)	0.0691 (16)	0.0164 (15)	−0.0158 (13)	0.0076 (15)
C15	0.092 (2)	0.0414 (12)	0.0874 (19)	−0.0048 (12)	−0.0021 (15)	−0.0067 (12)
C10	0.0579 (13)	0.0691 (14)	0.0500 (11)	0.0075 (11)	−0.0047 (10)	0.0066 (10)
C11	0.0552 (14)	0.0768 (18)	0.105 (2)	0.0165 (13)	0.0163 (14)	0.0124 (16)
C16	0.0815 (18)	0.0573 (14)	0.0833 (18)	0.0202 (13)	−0.0038 (14)	0.0190 (13)
O8	0.0582 (11)	0.0543 (10)	0.1301 (18)	−0.0180 (8)	0.0015 (11)	0.0029 (11)
Cl2	0.0510 (3)	0.0560 (3)	0.0761 (4)	−0.0096 (2)	0.0142 (3)	0.0077 (3)
Cl1	0.0534 (3)	0.0690 (4)	0.0694 (4)	0.0004 (3)	−0.0176 (3)	0.0018 (3)

O1—C14	1.345 (2)	C8—Cl2	1.7982 (19)
O1—C3	1.436 (2)	C8—H8	0.9800
O2—C13	1.347 (2)	C2—H2	0.9800
O2—C2	1.439 (2)	C7—Cl1	1.796 (2)
O3—C9	1.355 (2)	C7—H7	0.9800
O3—C6	1.436 (2)	C6—H6	0.9800
O4—C10	1.345 (3)	C13—C16	1.495 (3)
O4—C5	1.441 (2)	C4—H4	0.9800
O6—C9	1.199 (3)	C14—O8	1.197 (3)
C1—C2	1.531 (3)	C14—C15	1.484 (4)
C1—C6	1.534 (3)	C12—C10	1.493 (4)
C1—C7	1.536 (3)	C12—H12C	0.9600
C1—H1	0.9800	C12—H12A	0.9600
O7—C13	1.195 (3)	C12—H12B	0.9600
C3—C4	1.525 (3)	C15—H15A	0.9600
C3—C2	1.551 (3)	C15—H15B	0.9600
C3—H3	0.9800	C15—H15C	0.9600
O5—C10	1.173 (3)	C11—H11C	0.9600
C9—C11	1.484 (4)	C11—H11A	0.9600
C5—C4	1.528 (3)	C11—H11B	0.9600
C5—C6	1.552 (3)	C16—H16C	0.9600
C5—H5	0.9800	C16—H16B	0.9600
C8—C7	1.529 (3)	C16—H16A	0.9600
C8—C4	1.532 (3)
C14—O1—C3	116.52 (17)	O3—C6—C5	112.04 (17)
C13—O2—C2	116.86 (15)	C1—C6—C5	108.37 (16)
C9—O3—C6	116.31 (17)	O3—C6—H6	109.8
C10—O4—C5	117.68 (18)	C1—C6—H6	109.8
C2—C1—C6	108.32 (16)	C5—C6—H6	109.8
C2—C1—C7	113.02 (16)	O7—C13—O2	123.09 (19)
C6—C1—C7	104.95 (16)	O7—C13—C16	126.3 (2)
C2—C1—H1	110.1	O2—C13—C16	110.6 (2)
C6—C1—H1	110.1	C3—C4—C5	108.89 (16)
C7—C1—H1	110.1	C3—C4—C8	107.50 (15)
O1—C3—C4	106.24 (15)	C5—C4—C8	110.13 (16)
O1—C3—C2	112.40 (15)	C3—C4—H4	110.1
C4—C3—C2	109.19 (15)	C5—C4—H4	110.1
O1—C3—H3	109.6	C8—C4—H4	110.1
C4—C3—H3	109.6	O8—C14—O1	122.4 (2)
C2—C3—H3	109.6	O8—C14—C15	126.5 (2)
O6—C9—O3	123.0 (2)	O1—C14—C15	111.1 (2)
O6—C9—C11	126.0 (2)	C10—C12—H12C	109.5
O3—C9—C11	111.0 (2)	C10—C12—H12A	109.5
O4—C5—C4	108.96 (17)	H12C—C12—H12A	109.5
O4—C5—C6	109.03 (16)	C10—C12—H12B	109.5
C4—C5—C6	109.92 (15)	H12C—C12—H12B	109.5
O4—C5—H5	109.6	H12A—C12—H12B	109.5
C4—C5—H5	109.6	C14—C15—H15A	109.5
C6—C5—H5	109.6	C14—C15—H15B	109.5
C7—C8—C4	108.35 (16)	H15A—C15—H15B	109.5
C7—C8—Cl2	110.86 (13)	C14—C15—H15C	109.5
C4—C8—Cl2	110.69 (13)	H15A—C15—H15C	109.5
C7—C8—H8	109.0	H15B—C15—H15C	109.5
C4—C8—H8	109.0	O5—C10—O4	122.5 (2)
Cl2—C8—H8	109.0	O5—C10—C12	126.6 (3)
O2—C2—C1	111.44 (16)	O4—C10—C12	110.9 (2)
O2—C2—C3	107.67 (15)	C9—C11—H11C	109.5
C1—C2—C3	109.37 (15)	C9—C11—H11A	109.5
O2—C2—H2	109.4	H11C—C11—H11A	109.5
C1—C2—H2	109.4	C9—C11—H11B	109.5
C3—C2—H2	109.4	H11C—C11—H11B	109.5
C8—C7—C1	108.79 (16)	H11A—C11—H11B	109.5
C8—C7—Cl1	111.38 (14)	C13—C16—H16C	109.5
C1—C7—Cl1	112.85 (14)	C13—C16—H16B	109.5
C8—C7—H7	107.9	H16C—C16—H16B	109.5
C1—C7—H7	107.9	C13—C16—H16A	109.5
Cl1—C7—H7	107.9	H16C—C16—H16A	109.5
O3—C6—C1	107.03 (15)	H16B—C16—H16A	109.5
C14—O1—C3—C4	164.71 (17)	C2—C1—C6—O3	−53.5 (2)
C14—O1—C3—C2	−75.9 (2)	C7—C1—C6—O3	−174.44 (16)
C6—O3—C9—O6	2.1 (4)	C2—C1—C6—C5	67.6 (2)
C6—O3—C9—C11	−177.5 (2)	C7—C1—C6—C5	−53.4 (2)
C10—O4—C5—C4	105.8 (2)	O4—C5—C6—O3	−14.1 (2)
C10—O4—C5—C6	−134.2 (2)	C4—C5—C6—O3	105.27 (18)
C13—O2—C2—C1	−85.8 (2)	O4—C5—C6—C1	−131.97 (17)
C13—O2—C2—C3	154.22 (17)	C4—C5—C6—C1	−12.6 (2)
C6—C1—C2—O2	−172.81 (15)	C2—O2—C13—O7	3.9 (3)
C7—C1—C2—O2	−57.0 (2)	C2—O2—C13—C16	−175.8 (2)
C6—C1—C2—C3	−53.9 (2)	O1—C3—C4—C5	−172.47 (15)
C7—C1—C2—C3	62.0 (2)	C2—C3—C4—C5	66.09 (19)
O1—C3—C2—O2	−7.5 (2)	O1—C3—C4—C8	68.23 (19)
C4—C3—C2—O2	110.12 (17)	C2—C3—C4—C8	−53.2 (2)
O1—C3—C2—C1	−128.73 (16)	O4—C5—C4—C3	67.1 (2)
C4—C3—C2—C1	−11.1 (2)	C6—C5—C4—C3	−52.3 (2)
C4—C8—C7—C1	−23.6 (2)	O4—C5—C4—C8	−175.22 (15)
Cl2—C8—C7—C1	−145.30 (14)	C6—C5—C4—C8	65.4 (2)
C4—C8—C7—Cl1	−148.64 (13)	C7—C8—C4—C3	74.40 (19)
Cl2—C8—C7—Cl1	89.70 (15)	Cl2—C8—C4—C3	−163.84 (13)
C2—C1—C7—C8	−41.9 (2)	C7—C8—C4—C5	−44.1 (2)
C6—C1—C7—C8	75.91 (19)	Cl2—C8—C4—C5	77.66 (18)
C2—C1—C7—Cl1	82.20 (18)	C3—O1—C14—O8	−4.8 (3)
C6—C1—C7—Cl1	−159.95 (14)	C3—O1—C14—C15	174.3 (2)
C9—O3—C6—C1	−156.87 (19)	C5—O4—C10—O5	−1.7 (4)
C9—O3—C6—C5	84.5 (2)	C5—O4—C10—C12	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O6i	0.98	2.46	3.425 (3)	169
C8—H8···O8ii	0.98	2.42	3.377 (3)	166
C16—H16A···O7ii	0.96	2.53	3.416 (4)	154
C12—H12B···O5iii	0.96	2.52	3.297 (4)	137
C6—H6···O7iv	0.98	2.60	3.240 (3)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O6i	0.98	2.46	3.425 (3)	169
C8—H8⋯O8ii	0.98	2.42	3.377 (3)	166
C16—H16A⋯O7ii	0.96	2.53	3.416 (4)	154
C12—H12B⋯O5iii	0.96	2.52	3.297 (4)	137
C6—H6⋯O7iv	0.98	2.60	3.240 (3)	123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .