3-Hy-droxy-4-(3-hy-droxy-phen-yl)-2-quinolone monohydrate.

In the title compound, also known as viridicatol monohydrate, C(15)H(11)NO(3)·H(2)O, the dihedral angle between the benzene ring and quinoline ring system is 64.76 (5)°. An intra-molecular O-H⋯O hydrogen bond occurs. The crystal structure is stabilized by classical inter-molecular N-H⋯O and O-H⋯O hydrogen bonds and weak π-π inter-actions 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 = 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

Δρmax = 0.22 e Å−3

Δρmin = −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 ▶).

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

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

C15H11NO3·H2O	Z = 2
Mr = 271.26	F(000) = 284
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0774P)2 + 0.123P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2225 reflections	Δρmax = 0.22 e Å−3
184 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O2iv	0.86	2.04	2.8476 (18)	157.

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⋯O2iv	0.86	2.04	2.8476 (18)	157

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