(3R,4S)-3,4,8-Trihy-droxy-1,2,3,4-tetra-hydro-naphthalen-1-one monohydrate from Embellisia eureka.

In the title hydrate, C(10)H(10)O(4)·H(2)O, the six-membered aliphatic ring that is fused to the benzene ring has a sofa shape, with the hy-droxy group in the 3-position (that represents the sofa back) of the aliphatic ring occupying a quasi-axial position. The hy-droxy group of the aromatic ring is hydrogen-bond donor to the carbonyl O atom; other O-H⋯O hydrogen bonds link the organic mol-ecules and the water mol-ecules into a three-dimensional network.

Related literature

For the isolation of the title compound from other fungi, see: Borgschulte et al. (1991 ▶); Iwasaki et al. (1972 ▶); Trisuwan et al. (2008 ▶). The absolute configuration was assumed from published assignments, see: Trisuwan et al. (2008 ▶).

Experimental

Crystal data

C10H10O4·H2O

M = 212.20

Orthorhombic,

a = 4.6430 (4) Å

b = 14.3904 (11) Å

c = 14.4976 (10) Å

V = 968.65 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.31 × 0.28 × 0.24 mm

Data collection

Bruker APEX DUO diffractometer

6331 measured reflections

1320 independent reflections

916 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.096

S = 0.99

1320 reflections

156 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022623/xu5544sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022623/xu5544Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022623/xu5544Isup3.cml

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

C10H10O4·H2O	F(000) = 448
Mr = 212.20	Dx = 1.455 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1057 reflections
a = 4.6430 (4) Å	θ = 2.8–21.8°
b = 14.3904 (11) Å	µ = 0.12 mm−1
c = 14.4976 (10) Å	T = 293 K
V = 968.65 (13) Å3	Prism, brown
Z = 4	0.31 × 0.28 × 0.24 mm

Bruker APEX DUO diffractometer	916 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
ω scans	h = −6→5
6331 measured reflections	k = −18→17
1320 independent reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0507P)2] where P = (Fo2 + 2Fc2)/3
1320 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.21 e Å−3
5 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.5051 (5)	0.75199 (14)	0.74392 (14)	0.0280 (6)
O2	0.1740 (5)	0.83227 (14)	0.62424 (12)	0.0281 (5)
O3	0.1933 (5)	1.08380 (14)	0.69719 (15)	0.0262 (5)
O4	−0.0651 (5)	1.10191 (16)	0.87414 (16)	0.0318 (5)
O1w	0.0565 (5)	0.82560 (15)	0.43458 (14)	0.0268 (5)
C1	0.1862 (7)	0.8812 (2)	0.77911 (18)	0.0198 (6)
C2	0.3877 (7)	0.81217 (18)	0.80514 (18)	0.0226 (7)
C3	0.4788 (7)	0.8053 (2)	0.89602 (18)	0.0270 (7)
H3A	0.6084	0.7592	0.9134	0.032*
C4	0.3753 (7)	0.8673 (2)	0.96024 (19)	0.0278 (8)
H4A	0.4351	0.8622	1.0213	0.033*
C5	0.1843 (7)	0.9371 (2)	0.9362 (2)	0.0247 (7)
H5A	0.1202	0.9787	0.9809	0.030*
C6	0.0881 (7)	0.94556 (19)	0.8461 (2)	0.0211 (6)
C7	−0.1173 (7)	1.02214 (19)	0.8181 (2)	0.0244 (7)
H7	−0.3147	1.0008	0.8293	0.029*
C8	−0.0888 (7)	1.0480 (2)	0.7169 (2)	0.0235 (7)
H8	−0.2352	1.0942	0.7004	0.028*
C9	−0.1250 (6)	0.96220 (19)	0.6583 (2)	0.0236 (7)
H9A	−0.3192	0.9385	0.6658	0.028*
H9B	−0.0993	0.9786	0.5940	0.028*
C10	0.0858 (6)	0.88749 (19)	0.68341 (18)	0.0193 (6)
H1	0.439 (8)	0.761 (2)	0.6908 (13)	0.049 (12)*
H2	0.228 (12)	1.1339 (18)	0.725 (3)	0.103 (19)*
H3	−0.228 (4)	1.118 (3)	0.895 (2)	0.061 (13)*
H4	0.071 (10)	0.821 (2)	0.4923 (8)	0.060 (13)*
H5	0.212 (4)	0.848 (2)	0.414 (2)	0.039 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0361 (14)	0.0245 (12)	0.0236 (11)	0.0091 (10)	−0.0056 (11)	−0.0015 (10)
O2	0.0319 (12)	0.0308 (11)	0.0215 (10)	0.0076 (11)	−0.0046 (10)	−0.0056 (9)
O3	0.0207 (11)	0.0228 (12)	0.0351 (12)	−0.0052 (10)	0.0051 (10)	−0.0006 (10)
O4	0.0180 (11)	0.0354 (13)	0.0420 (13)	0.0034 (11)	0.0007 (11)	−0.0182 (11)
O1w	0.0195 (12)	0.0378 (13)	0.0231 (11)	−0.0054 (11)	−0.0032 (10)	0.0044 (10)
C1	0.0176 (15)	0.0199 (14)	0.0220 (14)	−0.0065 (12)	0.0019 (12)	0.0013 (12)
C2	0.0261 (17)	0.0187 (15)	0.0229 (14)	−0.0045 (13)	−0.0005 (13)	−0.0019 (12)
C3	0.034 (2)	0.0230 (16)	0.0243 (15)	−0.0021 (14)	−0.0067 (14)	0.0071 (14)
C4	0.034 (2)	0.0321 (17)	0.0175 (14)	−0.0094 (15)	−0.0003 (14)	0.0024 (13)
C5	0.0224 (16)	0.0282 (17)	0.0235 (15)	−0.0068 (14)	0.0066 (14)	−0.0030 (13)
C6	0.0153 (14)	0.0246 (15)	0.0234 (15)	−0.0070 (13)	0.0052 (13)	−0.0015 (12)
C7	0.0173 (16)	0.0263 (16)	0.0298 (16)	−0.0011 (13)	0.0007 (14)	−0.0069 (14)
C8	0.0157 (14)	0.0209 (15)	0.0340 (16)	0.0029 (13)	0.0003 (13)	0.0015 (13)
C9	0.0158 (16)	0.0299 (16)	0.0252 (16)	0.0005 (13)	−0.0031 (13)	−0.0006 (13)
C10	0.0155 (14)	0.0215 (14)	0.0211 (13)	−0.0048 (13)	−0.0004 (13)	0.0016 (12)

O1—C2	1.355 (3)	C3—H3A	0.9300
O1—H1	0.840 (10)	C4—C5	1.384 (4)
O2—C10	1.239 (3)	C4—H4A	0.9300
O3—C8	1.436 (4)	C5—C6	1.386 (4)
O3—H2	0.841 (10)	C5—H5A	0.9300
O4—C7	1.427 (3)	C6—C7	1.513 (4)
O4—H3	0.846 (10)	C7—C8	1.520 (4)
O1w—H4	0.842 (10)	C7—H7	0.9800
O1w—H5	0.846 (10)	C8—C9	1.508 (4)
C1—C6	1.417 (4)	C8—H8	0.9800
C1—C2	1.416 (4)	C9—C10	1.498 (4)
C1—C10	1.466 (4)	C9—H9A	0.9700
C2—C3	1.387 (4)	C9—H9B	0.9700
C3—C4	1.377 (4)
C2—O1—H1	111 (3)	O4—C7—C6	109.1 (2)
C8—O3—H2	113 (4)	O4—C7—C8	109.7 (2)
C7—O4—H3	106 (3)	C6—C7—C8	112.5 (3)
H4—O1w—H5	109 (4)	O4—C7—H7	108.5
C6—C1—C2	119.2 (2)	C6—C7—H7	108.5
C6—C1—C10	120.4 (3)	C8—C7—H7	108.5
C2—C1—C10	120.3 (2)	O3—C8—C9	106.4 (2)
O1—C2—C3	117.0 (3)	O3—C8—C7	111.0 (2)
O1—C2—C1	122.7 (2)	C9—C8—C7	109.5 (2)
C3—C2—C1	120.3 (3)	O3—C8—H8	109.9
C4—C3—C2	119.3 (3)	C9—C8—H8	109.9
C4—C3—H3A	120.3	C7—C8—H8	109.9
C2—C3—H3A	120.3	C10—C9—C8	112.2 (2)
C3—C4—C5	121.6 (3)	C10—C9—H9A	109.2
C3—C4—H4A	119.2	C8—C9—H9A	109.2
C5—C4—H4A	119.2	C10—C9—H9B	109.2
C4—C5—C6	120.5 (3)	C8—C9—H9B	109.2
C4—C5—H5A	119.8	H9A—C9—H9B	107.9
C6—C5—H5A	119.8	O2—C10—C1	120.7 (3)
C5—C6—C1	119.0 (3)	O2—C10—C9	120.5 (2)
C5—C6—C7	121.3 (3)	C1—C10—C9	118.8 (3)
C1—C6—C7	119.6 (3)
C6—C1—C2—O1	−175.8 (3)	C1—C6—C7—O4	−148.4 (3)
C10—C1—C2—O1	2.8 (4)	C5—C6—C7—C8	153.2 (3)
C6—C1—C2—C3	2.6 (4)	C1—C6—C7—C8	−26.4 (4)
C10—C1—C2—C3	−178.9 (3)	O4—C7—C8—O3	59.1 (3)
O1—C2—C3—C4	177.3 (3)	C6—C7—C8—O3	−62.5 (3)
C1—C2—C3—C4	−1.2 (4)	O4—C7—C8—C9	176.3 (2)
C2—C3—C4—C5	−0.6 (5)	C6—C7—C8—C9	54.7 (3)
C3—C4—C5—C6	1.0 (5)	O3—C8—C9—C10	63.4 (3)
C4—C5—C6—C1	0.5 (4)	C7—C8—C9—C10	−56.7 (3)
C4—C5—C6—C7	−179.1 (3)	C6—C1—C10—O2	178.9 (3)
C2—C1—C6—C5	−2.2 (4)	C2—C1—C10—O2	0.4 (4)
C10—C1—C6—C5	179.2 (3)	C6—C1—C10—C9	−0.8 (4)
C2—C1—C6—C7	177.4 (3)	C2—C1—C10—C9	−179.3 (3)
C10—C1—C6—C7	−1.1 (4)	C8—C9—C10—O2	−149.4 (3)
C5—C6—C7—O4	31.2 (4)	C8—C9—C10—C1	30.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.87 (3)	2.590 (3)	143 (3)
O1—H1···O1wi	0.84 (1)	2.27 (3)	2.829 (3)	124 (3)
O3—H2···O1ii	0.84 (1)	2.15 (3)	2.924 (3)	153 (5)
O4—H3···O1wiii	0.85 (1)	1.82 (1)	2.657 (3)	170 (4)
O1w—H4···O2	0.84 (1)	1.98 (1)	2.805 (3)	167 (4)
O1w—H5···O4iv	0.85 (1)	1.88 (1)	2.726 (3)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (1)	1.87 (3)	2.590 (3)	143 (3)
O1—H1⋯O1wi	0.84 (1)	2.27 (3)	2.829 (3)	124 (3)
O3—H2⋯O1ii	0.84 (1)	2.15 (3)	2.924 (3)	153 (5)
O4—H3⋯O1wiii	0.85 (1)	1.82 (1)	2.657 (3)	170 (4)
O1w—H4⋯O2	0.84 (1)	1.98 (1)	2.805 (3)	167 (4)
O1w—H5⋯O4iv	0.85 (1)	1.88 (1)	2.726 (3)	177 (3)

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