3-Hy­droxy-4-(3-hy­droxy­phen­yl)-2-quinolone monohydrate

Tao, Y.-W.; Wang, Y.

doi:10.1107/S160053681102945X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o2195-o2196

doi:10.1107/S160053681102945X

Open

access

3-Hydroxy-4-(3-hydroxyphenyl)-2-quinolone monohydrate

Yi-Wen Tao ^a and Yun Wang ^b ^*

^aSchool of Basic Science, Guangzhou Medical College, Guangzhou 510182, People's Republic of China, and ^bGuangdong Institute for Drug Control, Guangzhou 510180, People's Republic of China
^*Correspondence e-mail: yywentao@yahoo.com.cn

(Received 7 June 2011; accepted 21 July 2011; online 30 July 2011)

In the title compound, also known as viridicatol monohydrate, C₁₅H₁₁NO₃·H₂O, the dihedral angle between the benzene ring and quinoline ring system is 64.76 (5)°. An intramolecular O—H⋯O hydrogen bond occurs. The crystal structure is stabilized by classical intermolecular N—H⋯O and O—H⋯O hydrogen bonds and weak π–π interactions with a centroid–centroid distance of 3.8158 (10) Å.

Related literature

For 3-hydroxy-2(1H)-pyridinone, see: Deflon et al. (2000 ) and for 3-hydroxy-2-oxo-1,2-dihydroquinoline, see: Strashnova et al. (2008 ). For the isolation of viridicatol, see: Yurchenko et al. (2010 ); Fremlin et al. (2009 ); Proksch et al. (2008 ); Lund & Frisvad (1994 ); Birkinshaw et al. (1963 ); Kozlovskii et al. (2002 ). For the synthesis of viridicatol, see: Kobayashi & Harayama (2009 ). For examples of viridicatol derivatives, see: Bracken et al. (1954 ). For the biological activity of viridicatol, see: Lin et al. (2008 ); Proksch et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₅H₁₁NO₃·H₂O
M_r = 271.26
Triclinic, $[P \overline 1]$
a = 6.9845 (5) Å
b = 10.0632 (7) Å
c = 10.3361 (6) Å
α = 109.204 (6)°
β = 103.251 (5)°
γ = 101.015 (6)°
V = 639.12 (9) Å³
Z = 2
Cu Kα radiation
μ = 0.86 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.783, T_max = 0.958
5057 measured reflections
2225 independent reflections
1958 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.132
S = 1.10
2225 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.11	2.9577 (16)	169
O1—H1⋯O1W	0.82	1.92	2.689 (2)	155
O2—H2A⋯O3ⁱⁱ	0.82	1.99	2.6500 (16)	138
O2—H2A⋯O3	0.82	2.28	2.7242 (14)	115
O1W—H1B⋯O1Wⁱⁱⁱ	0.86	2.37	2.816 (3)	113
O1W—H1C⋯O2^iv	0.86	2.04	2.8476 (18)	157
Symmetry codes: (i) x, y, z-1; (ii) -x+3, -y+1, -z+1; (iii) -x+1, -y+1, -z+2; (iv) x-1, y, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102945X/bg2408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102945X/bg2408Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102945X/bg2408Isup3.mol

Supporting information file. DOI: 10.1107/S160053681102945X/bg2408Isup4.cml

checkCIF report

Comment top

3-hydroxy-4-(3-hydroxyphenyl)-2-quinolone, also known as viridicatol, C₁₅H₁₃NO₄ (I), was first isolated from Penicillium viridicatum Westling (Birkinshaw et al., 1963). It has been proven that viridicatol can completely inhibit the spleen lymphocytes proliferation (Lin et al., 2008) and suppress larval growth of the polyphagous pest insect Spodoptera littoralis (Proksch et al., 2008). Viridicatol can be isolated from Penicillium aurantiogriseum sensu lato (Lund et al., 1994), Penicillium chrysogenum strains (Kozlovskii et al., 2002), Penicillium sp from specimens of suberites domuncula (Proksch et al., 2008), an Australian marine-derived isolate of Aspergillus versicolor (Fremlin et al., 2009), and the marine fungus Aspergillus versicolor (Yurchenko et al., 2010). A similar compound, viridicatin, could be isolated from Penicillium cyclopium Westling (Bracken et al., 1954). Viridicatol also can be synthesized by one-pot method from cyanoacetanilides through Knoevenagel condensation followed by decyanative epoxide-arene cyclization (Kobayashi et al., 2009), but so far the crystal structure of viridicatol has not been reported.

The title compound can be considered as containing embedded 3-hydroxy-2(1H)-pyridinone, or 3-hydroxy-2-oxo-1,2-dihydroquinoline, motifs (Fig. 1). The crystal structures of both groups have already been reported (Deflon et al., 2000 and Strashnova et al., 2008) and their structural parameters are similar to those in I.

The 3-hydroxylbenzyl ring subtends a torsion angle of 64.76 (5)° to the quinoline to reduce the steric effect. The structure contains a water molecule which is involved in three out of the six hydrogen bonds formed (Table 1). The whole structure is a 3-D hydrogen-bonding architecture, futther stabilized by the weak π-π interaction between two pyridinone rings with a Cg1···Cg1 (2 - x,1 - y,1 - z) separation of 3.8158 (10) Å and the dihedral angle is zero (where Cg1 is the centroid of the N1/C7—C10/C15). Both weak interactions of hydrogen bonds and π-π effect consolidate the stability of the structure.

Related literature top

For 3-hydroxy-2(1H)-pyridinone, see: Deflon et al. (2000) and for 3-hydroxy-2-oxo-1,2-dihydroquinoline, see: Strashnova et al. (2008). For the isolation of viridicatol, see: Yurchenko et al. (2010); Fremlin et al. (2009); Proksch et al. (2008); Lund & Frisvad (1994); Birkinshaw et al. (1963); Kozlovskii et al. (2002). For the synthesis of viridicatol, see: Kobayashi & Harayama (2009). For examples of viridicatol derivatives, see: Bracken et al. (1954). For the biological activity of viridicatol, see: Lin et al. (2008); Proksch et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The fungus phomposis sp was isolated from the mangrove tree, Zhanjiang, and was stored at the Department of Applied Chemistry, Zhongshan University, Guangzhou, China. Starter cultures (from Professor Shining Zhou) were maintained on cornmeal seawater agar. Plugs of agar supporting mycelium growth were cut from solid culture medium and transferred aseptically to a 250 ml Erlenmeyer flask containing 100 ml liquid medium. The fungus was incubated at 28 °C and placed thirty days. The culture was filtered through cheesecloth. The mycelium was air-dried and then extracted in methanol. The CH₃OH extract of the fungal mycelium was chromatographed on silica gel by using a gradient from petroleum to ethyl acetate, then from acetate to methanol, and obtained viridicatol eluted with 50% ethyl acetate-petroleum ether. Colorless block crystals were grown from a solution in methanol at room temperature over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. The hydrogen bonds are shown as dashed lines.

3-hydroxy-4-(3-hydroxyphenyl)-1H-quinolin-2-one monohydrate top

Crystal data top

C₁₅H₁₁NO₃·H₂O	Z = 2
M_r = 271.26	F(000) = 284
Triclinic, P1	D_x = 1.410 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 6.9845 (5) Å	Cell parameters from 5194 reflections
b = 10.0632 (7) Å	θ = 4.8–69.4°
c = 10.3361 (6) Å	µ = 0.86 mm⁻¹
α = 109.204 (6)°	T = 298 K
β = 103.251 (5)°	Block, colorless
γ = 101.015 (6)°	0.30 × 0.20 × 0.05 mm
V = 639.12 (9) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2225 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 66.0°, θ_min = 4.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
T_min = 0.783, T_max = 0.958	k = −11→11
5057 measured reflections	l = −12→11

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0774P)² + 0.123P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2225 reflections	Δρ_max = 0.22 e Å⁻³
184 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (3)

Crystal data top

C₁₅H₁₁NO₃·H₂O	γ = 101.015 (6)°
M_r = 271.26	V = 639.12 (9) Å³
Triclinic, P1	Z = 2
a = 6.9845 (5) Å	Cu Kα radiation
b = 10.0632 (7) Å	µ = 0.86 mm⁻¹
c = 10.3361 (6) Å	T = 298 K
α = 109.204 (6)°	0.30 × 0.20 × 0.05 mm
β = 103.251 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2225 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1958 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.958	R_int = 0.018
5057 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.132	H-atom parameters constrained
S = 1.10	Δρ_max = 0.22 e Å⁻³
2225 reflections	Δρ_min = −0.27 e Å⁻³
184 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.0143 (2)	0.24292 (15)	0.66031 (14)	0.0370 (4)
C2	0.9196 (2)	0.30457 (16)	0.75933 (15)	0.0385 (4)
H2	0.8371	0.3630	0.7413	0.046*
C3	0.9479 (2)	0.27913 (17)	0.88547 (15)	0.0428 (4)
C4	1.0709 (3)	0.19305 (19)	0.91275 (17)	0.0516 (4)
H4	1.0906	0.1766	0.9976	0.062*
C5	1.1646 (3)	0.1315 (2)	0.81423 (18)	0.0542 (4)
H5	1.2471	0.0732	0.8328	0.065*
C6	1.1371 (3)	0.15549 (18)	0.68768 (17)	0.0474 (4)
H6	1.2004	0.1133	0.6213	0.057*
C7	0.9865 (2)	0.27142 (15)	0.52515 (14)	0.0359 (4)
C8	1.1501 (2)	0.34609 (16)	0.50295 (15)	0.0402 (4)
C9	1.1342 (2)	0.37555 (17)	0.37236 (16)	0.0401 (4)
C10	0.7706 (2)	0.24388 (16)	0.28851 (15)	0.0386 (4)
C11	0.5843 (3)	0.18891 (19)	0.17754 (17)	0.0504 (4)
H11	0.5750	0.2066	0.0938	0.061*
C12	0.4149 (3)	0.1087 (2)	0.19222 (19)	0.0565 (5)
H12	0.2913	0.0699	0.1171	0.068*
C13	0.4255 (3)	0.0846 (2)	0.31846 (19)	0.0533 (4)
H13	0.3088	0.0321	0.3285	0.064*
C14	0.6089 (2)	0.13873 (17)	0.42801 (17)	0.0439 (4)
H14	0.6150	0.1220	0.5119	0.053*
C15	0.7871 (2)	0.21856 (15)	0.41627 (14)	0.0361 (4)
N1	0.94503 (19)	0.32206 (14)	0.27371 (13)	0.0416 (3)
H1A	0.9317	0.3377	0.1956	0.050*
O1	0.8573 (2)	0.33744 (15)	0.98597 (12)	0.0589 (4)
H1	0.8083	0.3993	0.9673	0.088*
O2	1.33807 (17)	0.39862 (15)	0.60257 (12)	0.0576 (4)
H2A	1.4195	0.4438	0.5749	0.086*
O3	1.28439 (17)	0.44529 (14)	0.35328 (12)	0.0537 (4)
O1W	0.5902 (2)	0.4697 (2)	0.88892 (15)	0.0819 (5)
H1B	0.4875	0.4143	0.8981	0.098*
H1C	0.5456	0.4629	0.8014	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0379 (7)	0.0408 (7)	0.0291 (7)	0.0062 (6)	0.0054 (6)	0.0162 (6)
C2	0.0447 (8)	0.0449 (8)	0.0297 (7)	0.0136 (6)	0.0100 (6)	0.0201 (6)
C3	0.0505 (8)	0.0485 (8)	0.0297 (7)	0.0105 (7)	0.0108 (6)	0.0189 (6)
C4	0.0659 (10)	0.0592 (10)	0.0345 (8)	0.0197 (8)	0.0084 (7)	0.0283 (7)
C5	0.0641 (10)	0.0588 (10)	0.0450 (9)	0.0281 (8)	0.0084 (8)	0.0273 (8)
C6	0.0526 (9)	0.0534 (9)	0.0385 (8)	0.0207 (7)	0.0122 (7)	0.0192 (7)
C7	0.0408 (8)	0.0397 (7)	0.0283 (7)	0.0117 (6)	0.0106 (6)	0.0149 (6)
C8	0.0399 (8)	0.0484 (8)	0.0318 (8)	0.0104 (6)	0.0089 (6)	0.0180 (6)
C9	0.0432 (8)	0.0470 (8)	0.0349 (8)	0.0134 (6)	0.0149 (6)	0.0202 (6)
C10	0.0431 (8)	0.0422 (8)	0.0326 (7)	0.0134 (6)	0.0102 (6)	0.0178 (6)
C11	0.0523 (9)	0.0611 (10)	0.0385 (8)	0.0127 (8)	0.0041 (7)	0.0293 (8)
C12	0.0443 (9)	0.0672 (11)	0.0508 (10)	0.0068 (8)	−0.0037 (7)	0.0322 (8)
C13	0.0419 (8)	0.0615 (10)	0.0557 (10)	0.0062 (7)	0.0067 (7)	0.0327 (8)
C14	0.0438 (8)	0.0511 (8)	0.0395 (8)	0.0101 (7)	0.0104 (6)	0.0249 (7)
C15	0.0422 (8)	0.0385 (7)	0.0297 (7)	0.0134 (6)	0.0106 (6)	0.0156 (6)
N1	0.0471 (7)	0.0536 (7)	0.0300 (6)	0.0130 (6)	0.0121 (5)	0.0244 (6)
O1	0.0812 (9)	0.0802 (9)	0.0369 (6)	0.0369 (7)	0.0290 (6)	0.0349 (6)
O2	0.0408 (6)	0.0858 (9)	0.0426 (6)	−0.0010 (6)	0.0040 (5)	0.0379 (6)
O3	0.0456 (6)	0.0742 (8)	0.0509 (7)	0.0099 (6)	0.0170 (5)	0.0392 (6)
O1W	0.0676 (9)	0.1210 (13)	0.0514 (8)	0.0389 (9)	0.0136 (7)	0.0234 (8)

Geometric parameters (Å, º) top

C1—C2	1.385 (2)	C9—N1	1.351 (2)
C1—C6	1.389 (2)	C10—N1	1.3873 (19)
C1—C7	1.4941 (19)	C10—C11	1.392 (2)
C2—C3	1.388 (2)	C10—C15	1.409 (2)
C2—H2	0.9300	C11—C12	1.368 (2)
C3—O1	1.3659 (19)	C11—H11	0.9300
C3—C4	1.379 (2)	C12—C13	1.392 (2)
C4—C5	1.377 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.372 (2)
C5—C6	1.385 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.400 (2)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.352 (2)	N1—H1A	0.8600
C7—C15	1.447 (2)	O1—H1	0.8200
C8—O2	1.3492 (18)	O2—H2A	0.8200
C8—C9	1.459 (2)	O1W—H1B	0.8646
C9—O3	1.2393 (19)	O1W—H1C	0.8616

C2—C1—C6	119.79 (13)	N1—C9—C8	115.61 (13)
C2—C1—C7	120.22 (13)	N1—C10—C11	120.39 (13)
C6—C1—C7	119.99 (13)	N1—C10—C15	118.72 (13)
C1—C2—C3	119.98 (14)	C11—C10—C15	120.87 (14)
C1—C2—H2	120.0	C12—C11—C10	119.70 (14)
C3—C2—H2	120.0	C12—C11—H11	120.1
O1—C3—C4	117.93 (13)	C10—C11—H11	120.2
O1—C3—C2	121.98 (14)	C11—C12—C13	120.70 (15)
C4—C3—C2	120.09 (15)	C11—C12—H12	119.6
C5—C4—C3	119.96 (14)	C13—C12—H12	119.6
C5—C4—H4	120.0	C14—C13—C12	119.69 (15)
C3—C4—H4	120.0	C14—C13—H13	120.2
C4—C5—C6	120.54 (15)	C12—C13—H13	120.2
C4—C5—H5	119.7	C13—C14—C15	121.50 (14)
C6—C5—H5	119.7	C13—C14—H14	119.3
C5—C6—C1	119.64 (15)	C15—C14—H14	119.3
C5—C6—H6	120.2	C14—C15—C10	117.51 (13)
C1—C6—H6	120.2	C14—C15—C7	123.74 (13)
C8—C7—C15	119.29 (13)	C10—C15—C7	118.71 (13)
C8—C7—C1	119.73 (13)	C9—N1—C10	125.12 (12)
C15—C7—C1	120.97 (13)	C9—N1—H1A	117.4
O2—C8—C7	121.09 (13)	C10—N1—H1A	117.4
O2—C8—C9	116.39 (13)	C3—O1—H1	109.5
C7—C8—C9	122.52 (14)	C8—O2—H2A	109.5
O3—C9—N1	122.18 (13)	H1B—O1W—H1C	103.4
O3—C9—C8	122.21 (14)

C6—C1—C2—C3	0.1 (2)	C7—C8—C9—N1	−0.6 (2)
C7—C1—C2—C3	−179.25 (13)	N1—C10—C11—C12	178.30 (15)
C1—C2—C3—O1	−179.90 (14)	C15—C10—C11—C12	−0.2 (3)
C1—C2—C3—C4	0.3 (2)	C10—C11—C12—C13	1.6 (3)
O1—C3—C4—C5	179.72 (15)	C11—C12—C13—C14	−1.6 (3)
C2—C3—C4—C5	−0.5 (3)	C12—C13—C14—C15	0.2 (3)
C3—C4—C5—C6	0.2 (3)	C13—C14—C15—C10	1.1 (2)
C4—C5—C6—C1	0.2 (3)	C13—C14—C15—C7	−176.67 (15)
C2—C1—C6—C5	−0.4 (2)	N1—C10—C15—C14	−179.69 (13)
C7—C1—C6—C5	179.01 (15)	C11—C10—C15—C14	−1.1 (2)
C2—C1—C7—C8	115.56 (16)	N1—C10—C15—C7	−1.8 (2)
C6—C1—C7—C8	−63.8 (2)	C11—C10—C15—C7	176.81 (14)
C2—C1—C7—C15	−65.28 (19)	C8—C7—C15—C14	179.18 (14)
C6—C1—C7—C15	115.34 (16)	C1—C7—C15—C14	0.0 (2)
C15—C7—C8—O2	179.24 (13)	C8—C7—C15—C10	1.4 (2)
C1—C7—C8—O2	−1.6 (2)	C1—C7—C15—C10	−177.78 (12)
C15—C7—C8—C9	−0.2 (2)	O3—C9—N1—C10	−179.68 (14)
C1—C7—C8—C9	178.97 (13)	C8—C9—N1—C10	0.2 (2)
O2—C8—C9—O3	−0.2 (2)	C11—C10—N1—C9	−177.58 (15)
C7—C8—C9—O3	179.28 (15)	C15—C10—N1—C9	1.0 (2)
O2—C8—C9—N1	179.94 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.11	2.9577 (16)	169
O1—H1···O1W	0.82	1.92	2.689 (2)	155
O2—H2A···O3ⁱⁱ	0.82	1.99	2.6500 (16)	138
O2—H2A···O3	0.82	2.28	2.7242 (14)	115
O1W—H1B···O1Wⁱⁱⁱ	0.86	2.37	2.816 (3)	113
O1W—H1C···O2^iv	0.86	2.04	2.8476 (18)	157

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₃·H₂O
M_r	271.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.9845 (5), 10.0632 (7), 10.3361 (6)
α, β, γ (°)	109.204 (6), 103.251 (5), 101.015 (6)
V (Å³)	639.12 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.783, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	5057, 2225, 1958
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.132, 1.10
No. of reflections	2225
No. of parameters	184
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.11	2.9577 (16)	169.3
O1—H1···O1W	0.82	1.92	2.689 (2)	154.7
O2—H2A···O3ⁱⁱ	0.82	1.99	2.6500 (16)	137.6
O2—H2A···O3	0.82	2.28	2.7242 (14)	114.9
O1W—H1B···O1Wⁱⁱⁱ	0.86	2.37	2.816 (3)	112.8
O1W—H1C···O2^iv	0.86	2.04	2.8476 (18)	156.8

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

Acknowledgements

The authors thank the Fund of Guangzhou Science and Technology Program (2010Y1-C371), the Doctors to Start Research Fund of Guangzhou Medical College (2008 C25) and the Science Fund of the Education Bureau of Guangzhou City (10 A168) for financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Birkinshaw, J. H., Luckner, M., Mohammed, Y. S., Mothes, K. & Stickings, C. E. (1963). Biochem. J. 89, 196–202. PubMed CAS Web of Science Google Scholar
Bracken, A., Pocker, A. & Raistrick, H. (1954). Biochem. J. 57, 587–595. PubMed CAS Google Scholar
Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deflon, V. M., Bessler, K., Kretschmar, M. & Abram, U. (2000). Z. Anorg. Allg. Chem. 626, 1545–1549. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fremlin, L. J., Piggott, A. M., Lacey, E. & Capon, R. (2009). J. Nat. Prod., 72, 666–670. Web of Science CrossRef PubMed CAS Google Scholar
Kobayashi, Y. & Harayama, T. (2009). Org. Lett. 11, 1603–1606. Web of Science CrossRef PubMed CAS Google Scholar
Kozlovskii, A. G., Zhelifonova, V. P., Antipova, V. M., Shnyreva, A. V. & Viktorov, A. N. (2002). Microbiology, 71, 6666–6669. Web of Science CrossRef Google Scholar
Lin, J., Ke, A. B., Zhang, X. L., Zheng, Z. H., Zhu, J. T., Lu, X. H., Li, Y. Y., Gui, X. L., Shi, Y., Zhang, H. & He, J. G. (2008). Zhongguo Kangshengsu Zazhi, 33, 463–466. CAS Google Scholar
Lund, F. & Frisvad, J. C. (1994). Mycol. Res. 98, 481–492. CrossRef Google Scholar
Proksch, P., Ebel, R., Edrada, R., Riebe, F., Liu, H. B., Diesel, A., Bayer, M., Li, X., Lin, W. H., Grebenyuk, V., Mueller, W. E. G., Draeger, S. & Zuccaro, A. (2008). Botanica Marina, 51, 209–218. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Strashnova, S. B., Koval'chukova, O. V., Zaitsev, B. E. & Stash, A. I. (2008). Koord. Khim. 34, 783–787. CrossRef Google Scholar
Yurchenko, A. N., Smetanina, O. F., Kalinovsky, A. I., Pivkin, M. V., Dmitrenok, P. S. & Kuznetsova, T. A. (2010). Russ. Chem. Bull. 59, 852–856. Web of Science CrossRef CAS Google Scholar