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

Yi-Wen Tao; Yun Wang

doi:10.1107/S160053681102945X

. 2011 Jul 30;67(Pt 8):o2195–o2196. doi: 10.1107/S160053681102945X

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

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

PMCID: PMC3213626 PMID: 22091203

Abstract

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,
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[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 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

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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102945X/bg2408sup1.cif

e-67-o2195-sup1.cif^{(17.4KB, cif)}

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

e-67-o2195-Isup2.hkl^{(107.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102945X/bg2408Isup3.mol

Supplementary material file. DOI: 10.1107/S160053681102945X/bg2408Isup4.cml

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

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

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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.