3-[(R)-3,3-Dichloro-2-hydroxy­prop­yl]-8-hydr­oxy-6-meth­oxy-1H-isochromen-1-one

Huang, H.-R.; Fang, Y.-X.; Du, Z.-Y.; Zhang, K.; Lin, Y.-C.

doi:10.1107/S1600536808026391

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1801

doi:10.1107/S1600536808026391

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3-[(R)-3,3-Dichloro-2-hydroxypropyl]-8-hydroxy-6-methoxy-1H-isochromen-1-one

Hua-Rong Huang,^a ^* Yan-Xiong Fang,^a Zhi-Yun Du,^a Kun Zhang ^a and Yong-Cheng Lin ^b

^aFaculty of Light Industrial and Chemical Engineering, Guangdong University of Technology, Guangzhou 510090, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China
^*Correspondence e-mail: corihr@yahoo.com.cn

(Received 4 August 2008; accepted 15 August 2008; online 20 August 2008)

The title compound, C₁₃H₁₂Cl₂O₅, is an isocoumarin compound which has been isolated from the ethyl acetate extract of the fermentation broth of actinomycete Streptomyces sp. (V₄) from the South China Sea. There are intra- and intermolecular hydrogen bonds and halogen bonds [Cl⋯Cl = 3.434 (2) Å; C—Cl⋯Cl = 121.6°]. The intermolecular O—H⋯O hydrogen bonds link molecules into chains along the b axis.

Related literature

For related literature, see: Larsen & Breinholt (1999 ).

Experimental

Crystal data

C₁₃H₁₂Cl₂O₅
M_r = 319.13
Monoclinic, P 2₁
a = 9.483 (3) Å
b = 6.757 (2) Å
c = 10.548 (3) Å
β = 99.217 (5)°
V = 667.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 (2) K
0.50 × 0.34 × 0.21 mm

Data collection

Bruker SMART 1K area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.787, T_max = 0.902
4190 measured reflections
2524 independent reflections
2320 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.07
2524 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 931 Friedel pairs
Flack parameter: 0.06 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O3ⁱ	0.82	2.18	2.913 (3)	149
O3—H3⋯O2	0.82	1.91	2.624 (2)	145
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026391/ww2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026391/ww2128Isup2.hkl

checkCIF report

Comment top

As a kind of natural products from marine microorganisms, 3-((R)-3,3-dichloro-2-hydroxypropyl)-8-hydroxy-6-methoxy-1H- isochromen-1-one, is a isocoumarin-related dihydrodiaportin compound, from the fermentation broth of actinomycetes Streptomyces sp. (V4). In the primary biotest, the title compound showed weak activity inhibiting AchE in vitro (IC₅₀ = 3.9 uM/ml).

Larsen et al. also reported dichlorodiaportin (Larsen & Breinholt, 1999), but it was isolated from quite different microorganism, the typical cheese-associated isolates of Penicillium nalgiovense, and its structure was only elucidated based on spectral analysis, and the absolute configuration was depicted S by comparison with the optical rotation of those reported for several analogues of known absolute configuration. However, according to the optical rotation and our crystal structure, it is clear that Larsen's compound is the same compound as our dichlorodiaportin.

We report here the crystal structure of (I). Compound (I) crystallizes in space group P 2₁, and the 8-hydroxy-isochromen-1-one core rings in (I) is a planar conjugated ring system (Fig.1). In the crystal structure, there is an intra- molecular hydrogen bond [O···O = 2.624 (2) Å, and O—H···O = 144.6°] of O—H···O type between O3 and O5 hyroxyl groups in (I), and adjacent molecules form an infinite one-dimensional chain along b axis via O—H···O intermolecular hydrogen bonds [O···O = 2.913 (3)Å, and O—H···O = 149.0°] between the O3 and O5 hydroxyl groups (Fig.1 and Table 2).

Related literature top

For related literature, see: Larsen & Breinholt (1999).

Experimental top

A strain of streptomyces sp. (V₄) was isolated from the South China Sea, has been deposited in the School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, P. R. China.

Culture conditions: soluble starch 10 g l^-1, Ca carbonate 2 g l^-1, ammorium sulfate 2 g l^-1, dipotassium hydrogen phosphate 1 g l^-1, magnesium sulfate hydrated 1 g l^-1, sodium chloride 1 g l^-1, yeast extract 10 g l^-1, pH 7.2 and incubation at 298 K for 6 d. For the extraction and separation of the metabolite, the cultures (100 L) of (I) were filtered through cheesecloth. The filtrate was concentrated to 5L below 323 K, then extracted three times by shaking with an equal volume of ethyl acetate. The extract was evaporated under reduced pressure. The combined organic extracts were subjected to silica-gel column chromatography, eluting with petroleum ether/ethyl (1:1 v/v) acetate, to yield (I).

Colorless block crystals of (I) were obtained by evaporation of a methanol solution.

The compound identity was confirmed by NMR spectroscopy, Elemental Analysis, IR, FAB-MS, melting point and optical rotation.

¹H-NMR in CDCl₃ (500 MHz): 6.59 (s, 1H), 6,57 (d, J = 2.0 1H), 3.01 (m, 1H), 2.95 (m, 1H), 4.42 (m, 1H), 6.20 (d, J = 3.0 1H), 3.92 (s, 3H), 11.10 (s, OH) and 5.20 (d, J = 6.0, OH).

¹³C-NMR in CDCl₃ (125 MHz): 166.8 (C), 154 (C), 107.4 (CH), 140.4 (C), 102.1 (CH), 168.0 (C), 101.2 (CH), 164.3 (C), 111.4 (C), 37.3 (CH₂), 73.1 (CH), 77.2 (CH) and 56.3 (CH₃).

Elemental Analysis: C 48.91, H 3.97, calc. (for C₁₃H₁₂O₅C_l2): C 48.93, H 3.79%.

IR (KBr): 3474, 3032, 2986, 1693, 1643, 1568, 1465, 1356, 1237, 1197, 1096, 853, 790, 690.

FAB-MS: 319 [M]⁺, 321 [M+2]⁺, 235 [M-CHCl₂]⁺, 107, 77.

M.p. 419–420 K.

[α]²⁰_D = +7.8 (c = 0.05, MeOH).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecules in the asymmetric unit of (I), with anisotropic displacement parameters drawn at the 50% probability level.
	Fig. 2. A view of the hydrogen-bonded molecular chains (Dashed lines). The chains are aligned parallel to the crystallographic b axis. H atoms not involved in H-bonding have been omitted for clarity. Symmetry codes: (I) 1 - x,y - 1/2,-z; (II) 1 - x,1/2 + y,-z.
	Fig. 3. Supplementary figure.

3-[(R)-3,3-Dichloro-2-hydroxypropyl]-8-hydroxy-6-methoxy-1H-isochromen-1-one top

Crystal data top

C₁₃H₁₂Cl₂O₅	F(000) = 328
M_r = 319.13	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁	Melting point: 420 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.483 (3) Å	Cell parameters from 1002 reflections
b = 6.757 (2) Å	θ = 2.7–27.0°
c = 10.548 (3) Å	µ = 0.50 mm⁻¹
β = 99.217 (5)°	T = 293 K
V = 667.1 (4) Å³	Block, colorless
Z = 2	0.50 × 0.34 × 0.21 mm

Data collection top

Bruker SMART 1K area-detector diffractometer	2524 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 27.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.787, T_max = 0.902	k = −8→7
4190 measured reflections	l = −13→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0525P)² + 0.1606P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2524 reflections	Δρ_max = 0.26 e Å⁻³
184 parameters	Δρ_min = −0.39 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 931 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (8)

Crystal data top

C₁₃H₁₂Cl₂O₅	V = 667.1 (4) Å³
M_r = 319.13	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.483 (3) Å	µ = 0.50 mm⁻¹
b = 6.757 (2) Å	T = 293 K
c = 10.548 (3) Å	0.50 × 0.34 × 0.21 mm
β = 99.217 (5)°

Data collection top

Bruker SMART 1K area-detector diffractometer	2524 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2320 reflections with I > 2σ(I)
T_min = 0.787, T_max = 0.902	R_int = 0.019
4190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.26 e Å⁻³
S = 1.07	Δρ_min = −0.39 e Å⁻³
2524 reflections	Absolute structure: Flack (1983), 931 Friedel pairs
184 parameters	Absolute structure parameter: 0.06 (8)
1 restraint

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 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
C1	0.54937 (19)	0.4698 (4)	−0.06308 (18)	0.0334 (4)
C2	0.55042 (19)	0.4661 (4)	0.07326 (17)	0.0317 (4)
C3	0.6821 (2)	0.4688 (4)	0.15853 (18)	0.0356 (4)
C4	0.6830 (2)	0.4614 (4)	0.28857 (19)	0.0387 (4)
H4	0.7694	0.4607	0.3446	0.046*
C5	0.5540 (2)	0.4548 (4)	0.33695 (18)	0.0361 (4)
C6	0.4234 (2)	0.4543 (4)	0.25529 (18)	0.0369 (4)
H6	0.3383	0.4501	0.2884	0.044*
C7	0.42213 (19)	0.4602 (4)	0.12326 (17)	0.0332 (4)
C8	0.29092 (19)	0.4610 (4)	0.03216 (18)	0.0358 (4)
H8	0.2038	0.4583	0.0619	0.043*
C9	0.29283 (18)	0.4657 (4)	−0.09298 (17)	0.0332 (4)
C10	0.17165 (19)	0.4676 (5)	−0.20293 (17)	0.0356 (4)
H10A	0.1783	0.3505	−0.2548	0.043*
H10B	0.1821	0.5820	−0.2562	0.043*
C11	0.02418 (19)	0.4735 (5)	−0.16418 (17)	0.0393 (5)
H11	0.0161	0.3586	−0.1091	0.047*
C12	−0.0964 (2)	0.4600 (5)	−0.2789 (2)	0.0471 (5)
H12	−0.1876	0.4740	−0.2473	0.057*
C13	0.4413 (3)	0.4492 (5)	0.5247 (2)	0.0502 (5)
H13A	0.3875	0.5677	0.5015	0.075*
H13B	0.4673	0.4429	0.6163	0.075*
H13C	0.3843	0.3359	0.4950	0.075*
Cl1	−0.08373 (8)	0.65243 (17)	−0.39091 (7)	0.0803 (3)
Cl2	−0.09425 (9)	0.22660 (16)	−0.35406 (9)	0.0829 (3)
O1	0.42041 (13)	0.4685 (3)	−0.14183 (12)	0.0349 (3)
O2	0.65509 (15)	0.4724 (3)	−0.11589 (14)	0.0452 (4)
O3	0.80850 (14)	0.4768 (3)	0.11445 (14)	0.0459 (4)
H3	0.7939	0.4940	0.0365	0.069*
O4	0.56832 (17)	0.4506 (3)	0.46640 (14)	0.0463 (4)
O5	0.00051 (18)	0.6449 (3)	−0.09336 (15)	0.0524 (5)
H5	0.0323	0.7420	−0.1259	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0317 (8)	0.0335 (10)	0.0355 (9)	0.0005 (10)	0.0067 (7)	−0.0017 (10)
C2	0.0315 (8)	0.0309 (9)	0.0325 (9)	0.0027 (10)	0.0044 (7)	0.0009 (9)
C3	0.0321 (9)	0.0324 (10)	0.0414 (10)	0.0010 (11)	0.0034 (7)	−0.0001 (10)
C4	0.0363 (9)	0.0401 (10)	0.0367 (10)	0.0003 (11)	−0.0033 (7)	−0.0017 (11)
C5	0.0442 (10)	0.0323 (10)	0.0305 (9)	−0.0006 (11)	0.0016 (7)	−0.0008 (10)
C6	0.0364 (9)	0.0434 (11)	0.0316 (9)	0.0011 (11)	0.0072 (7)	0.0010 (10)
C7	0.0323 (9)	0.0363 (10)	0.0309 (9)	−0.0008 (11)	0.0046 (7)	−0.0008 (10)
C8	0.0287 (8)	0.0461 (11)	0.0330 (9)	0.0007 (11)	0.0067 (7)	0.0016 (11)
C9	0.0297 (8)	0.0352 (10)	0.0354 (9)	−0.0024 (10)	0.0070 (7)	−0.0031 (10)
C10	0.0330 (8)	0.0470 (11)	0.0271 (8)	0.0013 (11)	0.0058 (6)	−0.0018 (10)
C11	0.0333 (9)	0.0568 (13)	0.0281 (9)	−0.0076 (11)	0.0060 (7)	−0.0016 (11)
C12	0.0311 (9)	0.0760 (16)	0.0349 (10)	−0.0087 (14)	0.0074 (7)	−0.0079 (13)
C13	0.0613 (13)	0.0601 (15)	0.0300 (10)	0.0009 (15)	0.0095 (9)	0.0023 (11)
Cl1	0.0525 (4)	0.1251 (9)	0.0574 (4)	−0.0046 (4)	−0.0090 (3)	0.0333 (5)
Cl2	0.0561 (4)	0.1063 (7)	0.0842 (5)	−0.0205 (4)	0.0046 (4)	−0.0486 (5)
O1	0.0296 (6)	0.0467 (8)	0.0291 (6)	0.0006 (8)	0.0062 (5)	−0.0002 (7)
O2	0.0332 (7)	0.0632 (10)	0.0413 (7)	0.0014 (9)	0.0126 (6)	0.0000 (9)
O3	0.0313 (6)	0.0623 (10)	0.0434 (8)	0.0011 (9)	0.0038 (5)	0.0036 (9)
O4	0.0511 (8)	0.0562 (9)	0.0298 (7)	0.0021 (10)	0.0011 (6)	0.0012 (8)
O5	0.0412 (8)	0.0737 (13)	0.0441 (8)	0.0008 (9)	0.0120 (6)	−0.0175 (9)

Geometric parameters (Å, º) top

C1—O2	1.223 (2)	C9—C10	1.496 (2)
C1—O1	1.364 (2)	C10—C11	1.519 (2)
C1—C2	1.437 (3)	C10—H10A	0.9700
C2—C7	1.402 (2)	C10—H10B	0.9700
C2—C3	1.417 (2)	C11—O5	1.415 (3)
C3—O3	1.354 (2)	C11—C12	1.529 (3)
C3—C4	1.371 (3)	C11—H11	0.9800
C4—C5	1.400 (3)	C12—Cl2	1.766 (3)
C4—H4	0.9300	C12—Cl1	1.774 (3)
C5—O4	1.351 (2)	C12—H12	0.9800
C5—C6	1.390 (3)	C13—O4	1.437 (3)
C6—C7	1.391 (3)	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—C8	1.445 (2)	C13—H13C	0.9600
C8—C9	1.323 (3)	O3—H3	0.8200
C8—H8	0.9300	O5—H5	0.8200
C9—O1	1.389 (2)

O2—C1—O1	116.32 (17)	C9—C10—H10A	108.6
O2—C1—C2	125.56 (17)	C11—C10—H10A	108.6
O1—C1—C2	118.12 (16)	C9—C10—H10B	108.6
C7—C2—C3	119.41 (16)	C11—C10—H10B	108.6
C7—C2—C1	120.64 (16)	H10A—C10—H10B	107.6
C3—C2—C1	119.94 (16)	O5—C11—C10	113.2 (2)
O3—C3—C4	118.72 (17)	O5—C11—C12	107.8 (2)
O3—C3—C2	121.39 (17)	C10—C11—C12	112.93 (15)
C4—C3—C2	119.89 (17)	O5—C11—H11	107.6
C3—C4—C5	119.98 (17)	C10—C11—H11	107.6
C3—C4—H4	120.0	C12—C11—H11	107.6
C5—C4—H4	120.0	C11—C12—Cl2	110.3 (2)
O4—C5—C6	124.15 (19)	C11—C12—Cl1	111.17 (19)
O4—C5—C4	114.65 (17)	Cl2—C12—Cl1	110.42 (12)
C6—C5—C4	121.19 (17)	C11—C12—H12	108.3
C5—C6—C7	118.97 (18)	Cl2—C12—H12	108.3
C5—C6—H6	120.5	Cl1—C12—H12	108.3
C7—C6—H6	120.5	O4—C13—H13A	109.5
C6—C7—C2	120.54 (17)	O4—C13—H13B	109.5
C6—C7—C8	122.30 (17)	H13A—C13—H13B	109.5
C2—C7—C8	117.15 (16)	O4—C13—H13C	109.5
C9—C8—C7	121.02 (17)	H13A—C13—H13C	109.5
C9—C8—H8	119.5	H13B—C13—H13C	109.5
C7—C8—H8	119.5	C1—O1—C9	121.57 (14)
C8—C9—O1	121.48 (16)	C3—O3—H3	109.5
C8—C9—C10	129.93 (17)	C5—O4—C13	118.50 (15)
O1—C9—C10	108.59 (15)	C11—O5—H5	109.5
C9—C10—C11	114.68 (15)

O2—C1—C2—C7	−179.0 (3)	C1—C2—C7—C8	−0.9 (4)
O1—C1—C2—C7	0.4 (4)	C6—C7—C8—C9	−179.7 (3)
O2—C1—C2—C3	1.1 (4)	C2—C7—C8—C9	0.5 (4)
O1—C1—C2—C3	−179.5 (2)	C7—C8—C9—O1	0.4 (4)
C7—C2—C3—O3	−179.2 (2)	C7—C8—C9—C10	−179.9 (3)
C1—C2—C3—O3	0.7 (4)	C8—C9—C10—C11	2.8 (5)
C7—C2—C3—C4	1.4 (4)	O1—C9—C10—C11	−177.6 (2)
C1—C2—C3—C4	−178.7 (2)	C9—C10—C11—O5	61.4 (3)
O3—C3—C4—C5	179.4 (2)	C9—C10—C11—C12	−175.8 (3)
C2—C3—C4—C5	−1.2 (4)	O5—C11—C12—Cl2	−168.62 (15)
C3—C4—C5—O4	−179.1 (3)	C10—C11—C12—Cl2	65.6 (3)
C3—C4—C5—C6	0.4 (4)	O5—C11—C12—Cl1	68.5 (2)
O4—C5—C6—C7	179.6 (2)	C10—C11—C12—Cl1	−57.3 (3)
C4—C5—C6—C7	0.1 (4)	O2—C1—O1—C9	−180.0 (2)
C5—C6—C7—C2	0.1 (4)	C2—C1—O1—C9	0.6 (4)
C5—C6—C7—C8	−179.7 (3)	C8—C9—O1—C1	−1.0 (4)
C3—C2—C7—C6	−0.8 (4)	C10—C9—O1—C1	179.3 (2)
C1—C2—C7—C6	179.3 (3)	C6—C5—O4—C13	−1.2 (4)
C3—C2—C7—C8	179.0 (2)	C4—C5—O4—C13	178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3ⁱ	0.82	2.18	2.913 (3)	149
O3—H3···O2	0.82	1.91	2.624 (2)	145

Symmetry code: (i) −x+1, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂Cl₂O₅
M_r	319.13
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.483 (3), 6.757 (2), 10.548 (3)
β (°)	99.217 (5)
V (Å³)	667.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.50 × 0.34 × 0.21

Data collection
Diffractometer	Bruker SMART 1K area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.787, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	4190, 2524, 2320
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.07
No. of reflections	2524
No. of parameters	184
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.39
Absolute structure	Flack (1983), 931 Friedel pairs
Absolute structure parameter	0.06 (8)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3ⁱ	0.82	2.18	2.913 (3)	149.0
O3—H3···O2	0.82	1.91	2.624 (2)	144.6

Symmetry code: (i) −x+1, y+1/2, −z.

Acknowledgements

This work is supported by Guangdong Provincial Science Foundation.

References

Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Larsen, T. O. & Breinholt, J. (1999). J. Nat. Prod. 62, 1182–1184. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page o1801

doi:10.1107/S1600536808026391

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

3-[(R)-3,3-Di­chloro-2-hy­droxy­prop­yl]-8-hydr­­oxy-6-meth­­oxy-1H-isochromen-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-[(R)-3,3-Dichloro-2-hydroxypropyl]-8-hydroxy-6-methoxy-1H-isochromen-1-one