3-exo-Chloro-8-oxabicyclo-[3.2.1]oct-6-ene-2,4-diol chloro-form 0.33-solvate.

The title compound, 3C(7)H(9)ClO(3)·CHCl(3), crystallizes with mol-ecules of 3-exo-chloro-8-oxabicyclo-[3.2.1]oct-6-ene-2,4-diol (A) and chloro-form in a 3:1 ratio, in the space group R3m. Mol-ecules of A straddle a crystallographic mirror plane, whereas the chloro-form mol-ecules (C and H atoms) lie additionally on the threefold axis. The mol-ecules of A are linked into right- and left-helical chains by means of O-H⋯O hydrogen bonds, thus forming columns running along the c axis. Six inter-penetrated columns form a channel in which the solvent mol-ecules (chloro-form) are located.

Related literature

Inositetriphosphates analogues are potential prospective anti­tumoral compounds, see: Piettre et al. (1997 ▶); Miller & Allemann (2007 ▶).

Experimental

Crystal data

3C7H9ClO3·CHCl3

M = 649.16

Hexagonal,

a = 18.687 (5) Å

c = 6.8723 (16) Å

V = 2078.3 (9) Å3

Z = 3

Cu Kα radiation

μ = 6.09 mm−1

T = 295 K

0.1 × 0.07 × 0.06 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.530, T max = 0.694

1832 measured reflections

987 independent reflections

966 reflections with I > 2σ(I)

R int = 0.036

2 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.168

S = 1.18

987 reflections

69 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.51 e Å−3

Absolute structure: Flack (1983 ▶), 481 Friedel pairs

Flack parameter: −0.01 (2)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2000 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021898/si2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021898/si2178Isup2.hkl

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

3C7H9ClO3·CHCl3	Dx = 1.556 Mg m−3
Mr = 649.16	Melting point: decomposition K
Hexagonal, R3m	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: R 3 -2"	Cell parameters from 25 reflections
a = 18.687 (5) Å	θ = 32–45°
c = 6.8723 (16) Å	µ = 6.09 mm−1
V = 2078.3 (9) Å3	T = 295 K
Z = 3	Prism, colourless
F(000) = 1002	0.1 × 0.07 × 0.06 mm

Enraf–Nonius CAD-4 diffractometer	966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 71.9°, θmin = 4.7°
Nonprofiled ω scans	h = −22→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→22
Tmin = 0.530, Tmax = 0.694	l = −8→8
1832 measured reflections	2 standard reflections every 120 min
987 independent reflections	intensity decay: none

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.054	w = 1/[σ2(Fo2) + (0.021P)2 + 2.2041P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168	(Δ/σ)max = 0.001
S = 1.18	Δρmax = 0.28 e Å−3
987 reflections	Δρmin = −0.51 e Å−3
69 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0016 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 481 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (2)

Experimental. As the solvent molecules release from the crystal at ambient air, so the experiment was carried out from the crystal placed in a glass capillary.

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

	x	y	z	Uiso*/Ueq
Cl1	0.29956 (13)	0.14978 (7)	0.6438 (3)	0.0671 (7)
Cl2	0.61527 (5)	0.38473 (5)	0.7368 (3)	0.0619 (6)
O1	0.3605 (3)	0.0525 (2)	0.3740 (6)	0.0560 (10)
O2	0.5272 (3)	0.26359 (14)	0.3179 (9)	0.0583 (13)
C1	0.3610 (3)	0.18052 (16)	0.4256 (8)	0.0341 (12)
H1	0.3232	0.1616	0.3143	0.041*
C2	0.4122 (3)	0.1378 (2)	0.4156 (6)	0.0397 (10)
H2	0.4393	0.1436	0.5414	0.048*
C3	0.4782 (3)	0.1795 (3)	0.2586 (8)	0.0510 (12)
H3	0.5115	0.1527	0.2434	0.061*
C4	0.4419 (4)	0.1856 (3)	0.0684 (8)	0.0543 (12)
H4	0.4228	0.1467	−0.0311	0.065*
C5	0.6667	0.3333	0.654 (2)	0.048 (3)
H5	0.6667	0.3333	0.5111	0.058*
H11	0.361 (4)	0.024 (4)	0.453 (10)	0.063 (19)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0535 (11)	0.0777 (11)	0.0619 (10)	0.0268 (5)	0.0216 (8)	0.0108 (4)
Cl2	0.0497 (8)	0.0497 (8)	0.0932 (14)	0.0300 (8)	0.0052 (4)	−0.0052 (4)
O1	0.077 (3)	0.0298 (16)	0.058 (2)	0.0241 (18)	−0.0182 (19)	−0.0027 (15)
O2	0.026 (2)	0.054 (2)	0.085 (3)	0.0128 (11)	0.001 (2)	0.0003 (11)
C1	0.026 (3)	0.033 (2)	0.040 (3)	0.0132 (13)	−0.002 (2)	−0.0012 (11)
C2	0.039 (2)	0.0310 (19)	0.052 (2)	0.0196 (17)	−0.0126 (18)	−0.0054 (17)
C3	0.039 (2)	0.052 (3)	0.071 (3)	0.029 (2)	0.004 (2)	−0.003 (2)
C4	0.054 (3)	0.061 (3)	0.051 (2)	0.031 (2)	0.013 (2)	0.000 (2)
C5	0.033 (3)	0.033 (3)	0.078 (8)	0.0166 (16)	0.000	0.000

Cl1—C1	1.799 (6)	C2—C3	1.526 (7)
Cl2—C5	1.759 (5)	C2—H2	0.9800
O1—C2	1.420 (5)	C3—C4	1.503 (8)
O1—H11	0.77 (7)	C3—H3	0.9800
O2—C3i	1.426 (6)	C4—C4i	1.320 (11)
O2—C3	1.426 (6)	C4—H4	0.9300
C1—C2	1.524 (5)	C5—Cl2ii	1.759 (5)
C1—C2i	1.524 (5)	C5—Cl2iii	1.759 (5)
C1—H1	0.9800	C5—H5	0.9800
C2—O1—H11	114 (5)	O2—C3—C2	105.7 (4)
C3i—O2—C3	102.6 (5)	C4—C3—C2	111.9 (4)
C2—C1—C2i	113.8 (5)	O2—C3—H3	111.8
C2—C1—Cl1	109.8 (3)	C4—C3—H3	111.8
C2i—C1—Cl1	109.8 (3)	C2—C3—H3	111.8
C2—C1—H1	107.7	C4i—C4—C3	107.6 (3)
C2i—C1—H1	107.7	C4i—C4—H4	126.2
Cl1—C1—H1	107.7	C3—C4—H4	126.2
O1—C2—C1	110.1 (4)	Cl2ii—C5—Cl2iii	110.0 (4)
O1—C2—C3	110.7 (4)	Cl2ii—C5—Cl2	110.0 (4)
C1—C2—C3	108.8 (4)	Cl2iii—C5—Cl2	110.0 (4)
O1—C2—H2	109.1	Cl2ii—C5—H5	108.9
C1—C2—H2	109.1	Cl2iii—C5—H5	108.9
C3—C2—H2	109.1	Cl2—C5—H5	108.9
O2—C3—C4	103.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O1iv	0.77 (7)	1.98 (7)	2.723 (3)	162 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯O1i	0.77 (7)	1.98 (7)	2.723 (3)	162 (7)

Symmetry code: (i) .