(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one

Moumou, M.; Benharref, A.; Daran, J.-C.; Elhakmaoui, A.; Akssira, M.; Berraho, M.

doi:10.1107/S1600536811039717

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2826-o2827

doi:10.1107/S1600536811039717

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(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihydroxy-3,7-dimethyl-11-methylidene-13-oxabicyclo[8.3.0]tridec-6-en-12-one

Mohamed Moumou,^a Ahmed Benharref,^a Jean-Claude Daran,^b Ahmed Elhakmaoui,^c ^* Mohamed Akssira ^c and Moha Berraho ^a

^aLaboratoire de Chimie Biomoleculaire, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, ^bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France, and ^cLaboratoire de Chimie Bioorganique et Analytique, URAC 22. BP 146, FSTM, Université Hassan II, Mohammedia–Casablanca 20810 Mohammedia, Morocco
^*Correspondence e-mail: mberraho@yahoo.fr

(Received 12 September 2011; accepted 27 September 2011; online 5 October 2011)

The title compound, C₁₅H₂₁ClO₄, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the two rings is 66.4 (2)°. In the crystal, molecules are linked into chains propagating along the a axis by O—H⋯O hydrogen bonds.

Related literature

For the isolation and biological activity of 9α-hydroxyparthenolide, see: El Hassany et al. (2004 ). For the reactivity of this sesquiterpene, see: Castaneda-Acosta et al. (1993 ); Neukirch et al. (2003 ); Hwang et al. (2006 ); Neelakantan et al. (2009 ). For conformational analysis, see: Cremer & Pople (1975 )

Experimental

Crystal data

C₁₅H₂₁ClO₄
M_r = 300.77
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0224 (2) Å
b = 12.1532 (2) Å
c = 15.4147 (4) Å
V = 1502.90 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 180 K
0.35 × 0.27 × 0.17 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.889, T_max = 1.000
8982 measured reflections
3053 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.070
S = 1.04
3053 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 614 Friedel pairs
Flack parameter: −0.06 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.82	1.96	2.763 (1)	167
O4—H4⋯O3ⁱⁱ	0.82	2.17	2.980 (1)	171
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811039717/im2319sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039717/im2319Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039717/im2319Isup3.cml

checkCIF report

Comment top

Our work lies within the framework of the evaluation of medicinal plants and in particular, Anvillea radiata. The main constituent of the chloroform extract of the aerial parts of Anvillea radiata is 9α-hydroxyparthenolide (El Hassany et al., 2004). The reactivity of this sesquiterpene lactone and its derivatives has been the subject of several studies (Castaneda-Acosta et al., 1993; Neukirch et al., 2003; Hwang et al., 2006; Neelakantan et al., 2009), in order to prepare products with a high added value that can be used in the pharmacological industry. In the same context, we have treated 9α-hydroxyparthenolide with 5% of titanium tetrachloride (TiCl₄)and obtained (1S, 2R, 3R, 8R, 10S)-3-chloro-2,8- dihydroxy-3,7-dimethyl-11-methylene-13-oxabicyclo[8.3.0]tridec-6-en-12-one with a yield of 52%. The structure of this new product was determined by its single-crystal X-ray structure. The molecule contains two fused rings which exhibit different conformations. The molecular structure of the title compound, Fig.1, shows the lactone ring to adopt an envelope conformation, as indicated by Cremer & Pople (1975) puckering parameters QT = 0.147 (2) Å and ϕ2 = 58.1 (5)°. The ten-membered ring displays an approximate chair-chair conformation.In the crystal structure, molecules are linked into chains (Fig. 2) running along the a axis by intermolecular O—H···O hydrogen bonds (Table 1). Owing to the presence of Cl atom, the absolute configuration could be fully confirmed, by refining the Flack parameter (Flack, 1983) as C1(S), C2(R), C3(R), C8(R)and C10(S).

Related literature top

For the isolation and biological activity of 9α-hydroxyparthenolide, see: El Hassany et al. (2004); For the reactivity of this sesquiterpene, see: Castaneda-Acosta et al. (1993); Neukirch et al. (2003); Hwang et al. (2006); Neelakantan et al. (2009). For conformational analysis, see: Cremer & Pople (1975)

Experimental top

To a solution of 9α-hydroxyparthenolide (500 mg, 1.89 mmol) in 20 ml dichloromethane are added in small portions and carefully a catalytic amount (5%) of titanium tetrachloride (TiCl₄). The reaction mixture was kept at room temperature and stirred for 3 h. Afterwards it was hydrolysed with 20 ml of water and extracted three times with dichloromethane (20 mL). The organic phases are combined, dried over anhydrous Na₂SO₄ and then evaporated under reduced pressure. The resulting residue is purified by chromatography on silica gel with hexane /ethyl acetate (30/70) as eluent. This allowed us to isolate in pure 291 mg (0,98 mmol, 52%) of (1S, 2R, 3R, 8R, 10S)-3-chloro-2,8-dihydroxy-3,7-dimethyl-11-methylene- 13-oxabicyclo[8.3.0]tridec-6-en-12-one. The title compound was recrystallized from ethyl acetate to produce crystals suitable for X-ray diffraction.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. : Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. : Packing view showing the C–H···O hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

(1S,2R,3R,8R,10S)-3-Chloro-2,8- dihydroxy-3,7-dimethyl-11-methylidene-13-oxabicyclo[8.3.0]tridec-6-en-12-one top

Crystal data top

C₁₅H₂₁ClO₄	F(000) = 640
M_r = 300.77	D_x = 1.329 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8982 reflections
a = 8.0224 (2) Å	θ = 3.6–26.4°
b = 12.1532 (2) Å	µ = 0.26 mm⁻¹
c = 15.4147 (4) Å	T = 180 K
V = 1502.90 (6) Å³	Prism, colourless
Z = 4	0.35 × 0.27 × 0.17 mm

Data collection top

Agilent Xcalibur Eos Gemini ultra diffractometer	3053 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 16.1978 pixels mm^-1	θ_max = 26.4°, θ_min = 3.6°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −15→15
T_min = 0.889, T_max = 1.000	l = −18→19
8982 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0362P)² + 0.3492P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3053 reflections	Δρ_max = 0.21 e Å⁻³
185 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 614 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (5)

Crystal data top

C₁₅H₂₁ClO₄	V = 1502.90 (6) Å³
M_r = 300.77	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.0224 (2) Å	µ = 0.26 mm⁻¹
b = 12.1532 (2) Å	T = 180 K
c = 15.4147 (4) Å	0.35 × 0.27 × 0.17 mm

Data collection top

Agilent Xcalibur Eos Gemini ultra diffractometer	3053 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2944 reflections with I > 2σ(I)
T_min = 0.889, T_max = 1.000	R_int = 0.019
8982 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.070	Δρ_max = 0.21 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
3053 reflections	Absolute structure: Flack (1983), 614 Friedel pairs
185 parameters	Absolute structure parameter: −0.06 (5)
0 restraints

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent, 2010)

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 > 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

	x	y	z	U_iso*/U_eq
Cl	0.47204 (6)	0.42068 (3)	0.58743 (3)	0.03475 (11)
C1	0.60869 (16)	0.59828 (11)	0.36912 (9)	0.0169 (3)
H1	0.6725	0.5379	0.3432	0.020*
C2	0.55399 (17)	0.56590 (10)	0.46192 (9)	0.0169 (3)
H2	0.6465	0.5833	0.5011	0.020*
C3	0.51598 (18)	0.44248 (11)	0.47165 (9)	0.0193 (3)
C4	0.66321 (18)	0.36766 (11)	0.44947 (11)	0.0226 (3)
H4A	0.6774	0.3691	0.3870	0.027*
H4B	0.6322	0.2931	0.4651	0.027*
C5	0.83398 (18)	0.39143 (12)	0.49062 (11)	0.0271 (3)
H5A	0.8208	0.3935	0.5532	0.033*
H5B	0.9085	0.3310	0.4770	0.033*
C6	0.91472 (16)	0.49718 (12)	0.46184 (10)	0.0211 (3)
H6	0.9289	0.5519	0.5034	0.025*
C7	0.96724 (17)	0.51863 (11)	0.38212 (10)	0.0201 (3)
C8	1.01946 (18)	0.63373 (12)	0.35599 (10)	0.0213 (3)
H8	1.1106	0.6281	0.3139	0.026*
C9	0.87577 (18)	0.69698 (12)	0.31401 (10)	0.0231 (3)
H9A	0.8484	0.6619	0.2593	0.028*
H9B	0.9135	0.7711	0.3012	0.028*
C10	0.71583 (16)	0.70436 (11)	0.36933 (10)	0.0181 (3)
H10	0.7458	0.7230	0.4292	0.022*
C11	0.59596 (18)	0.78895 (13)	0.33507 (10)	0.0228 (3)
C12	0.44945 (19)	0.73049 (13)	0.29884 (11)	0.0264 (3)
C13	0.6075 (2)	0.89766 (13)	0.33538 (12)	0.0329 (4)
H13A	0.5217	0.9401	0.3123	0.039*
H13B	0.7013	0.9316	0.3587	0.039*
C14	0.9722 (2)	0.43627 (13)	0.30957 (11)	0.0296 (3)
H14A	0.9579	0.3636	0.3327	0.044*
H14B	1.0777	0.4409	0.2804	0.044*
H14C	0.8842	0.4517	0.2692	0.044*
C15	0.36070 (18)	0.40750 (12)	0.42250 (11)	0.0267 (3)
H15A	0.3759	0.4215	0.3617	0.040*
H15B	0.2666	0.4485	0.4433	0.040*
H15C	0.3415	0.3304	0.4314	0.040*
O1	0.33335 (15)	0.76689 (11)	0.25906 (9)	0.0408 (3)
O2	0.46321 (13)	0.62157 (8)	0.31574 (7)	0.0235 (2)
O3	0.41528 (12)	0.63183 (8)	0.48730 (7)	0.0219 (2)
H3	0.4483	0.6844	0.5159	0.033*
O4	1.07598 (12)	0.69787 (8)	0.42835 (8)	0.0261 (2)
H4	1.1646	0.6730	0.4461	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0427 (2)	0.03388 (19)	0.0276 (2)	0.00420 (18)	0.00966 (18)	0.00940 (16)
C1	0.0124 (6)	0.0175 (6)	0.0206 (7)	0.0001 (5)	−0.0032 (5)	0.0002 (5)
C2	0.0130 (6)	0.0169 (6)	0.0208 (7)	0.0019 (5)	0.0001 (5)	−0.0004 (5)
C3	0.0188 (7)	0.0195 (6)	0.0195 (7)	0.0008 (5)	0.0027 (6)	0.0042 (5)
C4	0.0204 (7)	0.0152 (6)	0.0322 (8)	0.0012 (5)	0.0019 (6)	0.0009 (6)
C5	0.0201 (7)	0.0237 (8)	0.0374 (9)	0.0051 (6)	−0.0026 (7)	0.0084 (6)
C6	0.0134 (6)	0.0208 (6)	0.0290 (8)	0.0032 (5)	−0.0038 (6)	−0.0013 (6)
C7	0.0109 (6)	0.0205 (6)	0.0289 (8)	0.0014 (5)	−0.0007 (6)	−0.0065 (6)
C8	0.0150 (7)	0.0231 (7)	0.0257 (7)	−0.0018 (5)	0.0029 (6)	−0.0057 (6)
C9	0.0200 (7)	0.0253 (7)	0.0240 (8)	−0.0045 (6)	0.0034 (6)	0.0022 (6)
C10	0.0155 (6)	0.0179 (6)	0.0208 (7)	−0.0011 (5)	−0.0002 (6)	0.0018 (6)
C11	0.0201 (7)	0.0255 (7)	0.0228 (8)	0.0007 (6)	0.0026 (6)	0.0061 (6)
C12	0.0217 (7)	0.0308 (8)	0.0267 (8)	−0.0005 (6)	0.0007 (7)	0.0100 (6)
C13	0.0331 (9)	0.0247 (8)	0.0408 (10)	0.0031 (7)	0.0023 (8)	0.0073 (7)
C14	0.0240 (8)	0.0288 (8)	0.0361 (9)	−0.0018 (6)	0.0042 (7)	−0.0135 (7)
C15	0.0191 (7)	0.0201 (7)	0.0410 (9)	−0.0039 (6)	−0.0041 (7)	0.0039 (7)
O1	0.0255 (6)	0.0461 (7)	0.0507 (8)	0.0016 (5)	−0.0121 (6)	0.0243 (6)
O2	0.0193 (5)	0.0256 (5)	0.0255 (5)	−0.0039 (4)	−0.0078 (5)	0.0052 (4)
O3	0.0156 (5)	0.0193 (5)	0.0308 (6)	0.0022 (4)	0.0021 (4)	−0.0050 (4)
O4	0.0169 (5)	0.0233 (5)	0.0380 (7)	0.0005 (4)	−0.0052 (4)	−0.0100 (5)

Geometric parameters (Å, º) top

Cl—C3	1.8384 (15)	C8—C9	1.529 (2)
C1—O2	1.4557 (16)	C8—H8	0.9800
C1—C2	1.5471 (19)	C9—C10	1.5433 (19)
C1—C10	1.5495 (18)	C9—H9A	0.9700
C1—H1	0.9800	C9—H9B	0.9700
C2—O3	1.4260 (16)	C10—C11	1.504 (2)
C2—C3	1.5380 (18)	C10—H10	0.9800
C2—H2	0.9800	C11—C13	1.324 (2)
C3—C15	1.519 (2)	C11—C12	1.483 (2)
C3—C4	1.5292 (19)	C12—O1	1.1997 (19)
C4—C5	1.537 (2)	C12—O2	1.3536 (18)
C4—H4A	0.9700	C13—H13A	0.9300
C4—H4B	0.9700	C13—H13B	0.9300
C5—C6	1.506 (2)	C14—H14A	0.9600
C5—H5A	0.9700	C14—H14B	0.9600
C5—H5B	0.9700	C14—H14C	0.9600
C6—C7	1.325 (2)	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C14	1.5014 (19)	C15—H15C	0.9600
C7—C8	1.5148 (19)	O3—H3	0.8200
C8—O4	1.4343 (17)	O4—H4	0.8200

O2—C1—C2	110.16 (11)	O4—C8—H8	108.5
O2—C1—C10	106.51 (10)	C7—C8—H8	108.5
C2—C1—C10	111.53 (11)	C9—C8—H8	108.5
O2—C1—H1	109.5	C8—C9—C10	114.96 (12)
C2—C1—H1	109.5	C8—C9—H9A	108.5
C10—C1—H1	109.5	C10—C9—H9A	108.5
O3—C2—C3	111.50 (11)	C8—C9—H9B	108.5
O3—C2—C1	109.40 (11)	C10—C9—H9B	108.5
C3—C2—C1	113.23 (11)	H9A—C9—H9B	107.5
O3—C2—H2	107.5	C11—C10—C9	112.17 (12)
C3—C2—H2	107.5	C11—C10—C1	102.32 (11)
C1—C2—H2	107.5	C9—C10—C1	114.31 (12)
C15—C3—C4	110.83 (12)	C11—C10—H10	109.3
C15—C3—C2	112.77 (11)	C9—C10—H10	109.3
C4—C3—C2	113.89 (11)	C1—C10—H10	109.3
C15—C3—Cl	106.66 (10)	C13—C11—C12	122.32 (15)
C4—C3—Cl	106.23 (10)	C13—C11—C10	129.51 (15)
C2—C3—Cl	105.86 (9)	C12—C11—C10	108.16 (13)
C3—C4—C5	118.97 (12)	O1—C12—O2	121.48 (15)
C3—C4—H4A	107.6	O1—C12—C11	129.15 (15)
C5—C4—H4A	107.6	O2—C12—C11	109.36 (13)
C3—C4—H4B	107.6	C11—C13—H13A	120.0
C5—C4—H4B	107.6	C11—C13—H13B	120.0
H4A—C4—H4B	107.0	H13A—C13—H13B	120.0
C6—C5—C4	114.97 (12)	C7—C14—H14A	109.5
C6—C5—H5A	108.5	C7—C14—H14B	109.5
C4—C5—H5A	108.5	H14A—C14—H14B	109.5
C6—C5—H5B	108.5	C7—C14—H14C	109.5
C4—C5—H5B	108.5	H14A—C14—H14C	109.5
H5A—C5—H5B	107.5	H14B—C14—H14C	109.5
C7—C6—C5	125.30 (14)	C3—C15—H15A	109.5
C7—C6—H6	117.3	C3—C15—H15B	109.5
C5—C6—H6	117.3	H15A—C15—H15B	109.5
C6—C7—C14	124.62 (13)	C3—C15—H15C	109.5
C6—C7—C8	121.08 (13)	H15A—C15—H15C	109.5
C14—C7—C8	114.22 (12)	H15B—C15—H15C	109.5
O4—C8—C7	112.49 (12)	C12—O2—C1	111.36 (11)
O4—C8—C9	107.12 (11)	C2—O3—H3	109.5
C7—C8—C9	111.61 (12)	C8—O4—H4	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.96	2.763 (1)	167
O4—H4···O3ⁱⁱ	0.82	2.17	2.980 (1)	171

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁ClO₄
M_r	300.77
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	8.0224 (2), 12.1532 (2), 15.4147 (4)
V (Å³)	1502.90 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.35 × 0.27 × 0.17

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.889, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8982, 3053, 2944
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.070, 1.04
No. of reflections	3053
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21
Absolute structure	Flack (1983), 614 Friedel pairs
Absolute structure parameter	−0.06 (5)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.96	2.763 (1)	167
O4—H4···O3ⁱⁱ	0.82	2.17	2.980 (1)	171

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1, y, z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for financial support.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2826-o2827

doi:10.1107/S1600536811039717

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­dr­oxy-3,7-di­methyl-11-methyl­­idene-13-oxabi­cyclo­[8.3.0]tridec-6-en-12-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihydroxy-3,7-dimethyl-11-methylidene-13-oxabicyclo[8.3.0]tridec-6-en-12-one