3-[(R)-3,3-Dichloro-2-hydroxy-prop-yl]-8-hydr-oxy-6-meth-oxy-1H-isochromen-1-one.

The title compound, C(13)H(12)Cl(2)O(5), is an isocoumarin compound which has been isolated from the ethyl acetate extract of the fermentation broth of actinomycete Streptomyces sp. (V(4)) from the South China Sea. There are intra- and inter-molecular hydrogen bonds and halogen bonds [Cl⋯Cl = 3.434 (2) Å; C-Cl⋯Cl = 121.6°]. The intermolecular O-H⋯O hydrogen bonds link mol-ecules into chains along the b axis.

Related literature

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

Experimental

Crystal data

C13H12Cl2O5

M = 319.13

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.07

2524 reflections

184 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 931 Friedel pairs

Flack parameter: 0.06 (8)

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.

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

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

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

C13H12Cl2O5	F000 = 328
Mr = 319.13	Dx = 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 = 2.7–27.0º
c = 10.548 (3) Å	µ = 0.50 mm−1
β = 99.217 (5)º	T = 293 (2) K
V = 667.1 (4) Å3	Block, colorless
Z = 2	0.50 × 0.34 × 0.21 mm

Bruker SMART 1K area-detector diffractometer	2524 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 293(2) K	θmax = 27.1º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.787, Tmax = 0.902	k = −8→7
4190 measured reflections	l = −13→11

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.1606P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.26 e Å−3
2524 reflections	Δρmin = −0.39 e Å−3
184 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 931 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (8)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .