1,6-Dihydr-oxy-3-hydroxy-methyl-8-methoxy-anthracene-9,10-dione monohydrate.

The title compound, C(16)H(12)O(6)·H(2)O, isolated from the halotolerant fungus Aspergillus variecolor B-17, is also known as questinol monohydrate. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network. π-π stacking inter-actions consolidate the supra-molecular structure [the shortest inter-planar distances are 3.456 (3), 3.366 (4) and 3.382 (4) Å].

Related literature

For general background, see: Stickings & Mahmoodian (1962 ▶); Slater et al. (1971 ▶); Kimura et al. (1983 ▶); Arai et al. (1989 ▶); Nielsen et al. (2004 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C16H12O6·H2O

M = 318.27

Monoclinic,

a = 11.3317 (11) Å

b = 16.7515 (19) Å

c = 7.2193 (9) Å

β = 95.453 (2)°

V = 1364.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 (2) K

0.18 × 0.14 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.978, T max = 0.994

7003 measured reflections

2404 independent reflections

1108 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.099

S = 1.01

2404 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: XP (Siemens, 1994 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066986/bq2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066986/bq2051Isup2.hkl

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

C16H12O6·H2O	F000 = 664
Mr = 318.27	Dx = 1.550 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 901 reflections
a = 11.3317 (11) Å	θ = 2.2–25.2º
b = 16.7515 (19) Å	µ = 0.12 mm−1
c = 7.2193 (9) Å	T = 298 (2) K
β = 95.453 (2)º	Flake, yellow
V = 1364.2 (3) Å3	0.18 × 0.14 × 0.05 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2404 independent reflections
Radiation source: fine-focus sealed tube	1108 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.090
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −13→10
Tmin = 0.978, Tmax = 0.994	k = −19→19
7003 measured reflections	l = −8→7

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0163P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2404 reflections	Δρmax = 0.23 e Å−3
208 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.47014 (19)	0.62825 (13)	0.9624 (3)	0.0409 (7)
H1	0.4927	0.5828	0.9423	0.061*
O2	0.4486 (2)	0.91888 (13)	0.8924 (3)	0.0452 (7)
H2	0.4215	0.9337	0.7887	0.068*
O3	0.9454 (2)	0.74461 (14)	0.7759 (4)	0.0548 (8)
O4	1.1510 (2)	0.48495 (14)	0.6863 (3)	0.0489 (7)
H4	1.1898	0.5246	0.6644	0.073*
O5	0.77278 (19)	0.40952 (13)	0.8557 (3)	0.0446 (7)
O6	0.6237 (2)	0.52178 (13)	0.9245 (3)	0.0419 (7)
O7	0.2909 (2)	0.61113 (14)	0.6547 (3)	0.0609 (8)
H7A	0.3423	0.6145	0.7481	0.073*
H7B	0.3279	0.6016	0.5601	0.073*
C1	0.5559 (3)	0.6817 (2)	0.9249 (4)	0.0302 (9)
C2	0.5248 (3)	0.76155 (18)	0.9251 (4)	0.0316 (9)
H2A	0.4486	0.7763	0.9485	0.038*
C3	0.6068 (3)	0.8194 (2)	0.8904 (4)	0.0303 (9)
C4	0.7203 (3)	0.79692 (18)	0.8534 (4)	0.0314 (9)
H4A	0.7757	0.8358	0.8308	0.038*
C5	0.7514 (3)	0.7171 (2)	0.8500 (4)	0.0290 (8)
C6	0.8705 (3)	0.6940 (2)	0.8020 (4)	0.0334 (9)
C7	0.9000 (3)	0.60779 (19)	0.7896 (4)	0.0294 (9)
C8	1.0101 (3)	0.5876 (2)	0.7384 (4)	0.0363 (9)
H8	1.0626	0.6274	0.7094	0.044*
C9	1.0428 (3)	0.5076 (2)	0.7301 (4)	0.0351 (9)
C10	0.9635 (3)	0.4471 (2)	0.7656 (4)	0.0366 (10)
H10	0.9851	0.3939	0.7549	0.044*
C11	0.8527 (3)	0.4668 (2)	0.8167 (4)	0.0334 (9)
C12	0.8161 (3)	0.54798 (19)	0.8292 (4)	0.0285 (8)
C13	0.7004 (3)	0.5714 (2)	0.8841 (4)	0.0304 (9)
C14	0.6699 (3)	0.65733 (19)	0.8854 (4)	0.0278 (8)
C15	0.5733 (3)	0.90622 (19)	0.8933 (4)	0.0393 (9)
H15A	0.6132	0.9309	1.0036	0.047*
H15B	0.6010	0.9324	0.7856	0.047*
C16	0.8055 (3)	0.3271 (2)	0.8389 (5)	0.0564 (12)
H16A	0.8225	0.3165	0.7135	0.085*
H16B	0.7413	0.2936	0.8694	0.085*
H16C	0.8746	0.3160	0.9226	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0374 (16)	0.0249 (15)	0.0619 (17)	−0.0027 (12)	0.0123 (13)	−0.0018 (12)
O2	0.0414 (16)	0.0392 (16)	0.0558 (17)	0.0107 (13)	0.0084 (13)	0.0035 (12)
O3	0.0387 (17)	0.0291 (16)	0.100 (2)	−0.0081 (13)	0.0226 (15)	0.0001 (14)
O4	0.0384 (16)	0.0398 (17)	0.0711 (19)	0.0066 (13)	0.0182 (14)	0.0000 (13)
O5	0.0337 (15)	0.0244 (15)	0.0771 (19)	0.0011 (13)	0.0122 (14)	−0.0005 (14)
O6	0.0333 (15)	0.0244 (15)	0.0702 (18)	−0.0049 (12)	0.0167 (13)	0.0007 (12)
O7	0.0491 (18)	0.073 (2)	0.0616 (18)	−0.0052 (15)	0.0096 (14)	−0.0054 (15)
C1	0.029 (2)	0.029 (2)	0.032 (2)	−0.0075 (18)	0.0036 (18)	−0.0010 (16)
C2	0.033 (2)	0.025 (2)	0.038 (2)	0.0050 (18)	0.0069 (18)	0.0032 (16)
C3	0.039 (2)	0.022 (2)	0.030 (2)	0.0024 (19)	0.0027 (18)	−0.0010 (15)
C4	0.033 (2)	0.023 (2)	0.039 (2)	−0.0027 (18)	0.0053 (17)	0.0039 (17)
C5	0.028 (2)	0.030 (2)	0.030 (2)	−0.0011 (18)	0.0053 (17)	0.0013 (16)
C6	0.033 (2)	0.027 (2)	0.041 (2)	−0.0038 (19)	0.0032 (18)	−0.0011 (17)
C7	0.029 (2)	0.028 (2)	0.032 (2)	−0.0014 (18)	0.0073 (17)	0.0002 (16)
C8	0.036 (2)	0.032 (2)	0.043 (2)	−0.001 (2)	0.0117 (18)	0.0018 (18)
C9	0.028 (2)	0.042 (3)	0.036 (2)	0.009 (2)	0.0072 (18)	−0.0001 (18)
C10	0.034 (2)	0.031 (2)	0.045 (2)	0.0034 (18)	0.0025 (19)	−0.0053 (17)
C11	0.028 (2)	0.031 (2)	0.040 (2)	−0.0017 (19)	0.0008 (18)	−0.0001 (17)
C12	0.024 (2)	0.027 (2)	0.035 (2)	0.0004 (18)	0.0047 (17)	−0.0012 (16)
C13	0.029 (2)	0.034 (2)	0.028 (2)	−0.0038 (19)	−0.0002 (17)	−0.0044 (17)
C14	0.030 (2)	0.026 (2)	0.027 (2)	0.0021 (17)	0.0045 (17)	−0.0017 (15)
C15	0.042 (2)	0.035 (2)	0.041 (2)	0.002 (2)	0.0071 (19)	−0.0018 (18)
C16	0.061 (3)	0.020 (2)	0.089 (3)	0.003 (2)	0.013 (2)	0.002 (2)

O1—C1	1.368 (3)	C4—H4A	0.9300
O1—H1	0.8200	C5—C14	1.403 (4)
O2—C15	1.428 (3)	C5—C6	1.476 (4)
O2—H2	0.8200	C6—C7	1.486 (4)
O3—C6	1.227 (3)	C7—C8	1.376 (4)
O4—C9	1.349 (3)	C7—C12	1.428 (4)
O4—H4	0.8200	C8—C9	1.394 (4)
O5—C11	1.367 (4)	C8—H8	0.9300
O5—C16	1.439 (4)	C9—C10	1.394 (4)
O6—C13	1.256 (3)	C10—C11	1.382 (4)
O7—H7A	0.8500	C10—H10	0.9300
O7—H7B	0.8500	C11—C12	1.428 (4)
C1—C2	1.382 (4)	C12—C13	1.460 (4)
C1—C14	1.409 (4)	C13—C14	1.481 (4)
C2—C3	1.381 (4)	C15—H15A	0.9700
C2—H2A	0.9300	C15—H15B	0.9700
C3—C4	1.390 (4)	C16—H16A	0.9600
C3—C15	1.504 (4)	C16—H16B	0.9600
C4—C5	1.383 (4)	C16—H16C	0.9600
C1—O1—H1	109.5	O4—C9—C10	117.0 (3)
C15—O2—H2	109.5	C8—C9—C10	120.9 (3)
C9—O4—H4	109.5	C11—C10—C9	119.6 (3)
C11—O5—C16	118.3 (3)	C11—C10—H10	120.2
H7A—O7—H7B	107.3	C9—C10—H10	120.2
O1—C1—C2	116.6 (3)	O5—C11—C10	121.7 (3)
O1—C1—C14	122.1 (3)	O5—C11—C12	116.9 (3)
C2—C1—C14	121.3 (3)	C10—C11—C12	121.4 (3)
C3—C2—C1	120.1 (3)	C11—C12—C7	116.9 (3)
C3—C2—H2A	119.9	C11—C12—C13	123.2 (3)
C1—C2—H2A	119.9	C7—C12—C13	119.9 (3)
C2—C3—C4	119.7 (3)	O6—C13—C12	123.0 (3)
C2—C3—C15	120.0 (3)	O6—C13—C14	118.3 (3)
C4—C3—C15	120.3 (3)	C12—C13—C14	118.6 (3)
C5—C4—C3	120.5 (3)	C5—C14—C1	117.5 (3)
C5—C4—H4A	119.8	C5—C14—C13	122.3 (3)
C3—C4—H4A	119.8	C1—C14—C13	120.2 (3)
C4—C5—C14	120.9 (3)	O2—C15—C3	113.2 (3)
C4—C5—C6	119.9 (3)	O2—C15—H15A	108.9
C14—C5—C6	119.2 (3)	C3—C15—H15A	108.9
O3—C6—C5	121.0 (3)	O2—C15—H15B	108.9
O3—C6—C7	120.0 (3)	C3—C15—H15B	108.9
C5—C6—C7	119.0 (3)	H15A—C15—H15B	107.7
C8—C7—C12	121.3 (3)	O5—C16—H16A	109.5
C8—C7—C6	118.0 (3)	O5—C16—H16B	109.5
C12—C7—C6	120.8 (3)	H16A—C16—H16B	109.5
C7—C8—C9	119.9 (3)	O5—C16—H16C	109.5
C7—C8—H8	120.0	H16A—C16—H16C	109.5
C9—C8—H8	120.0	H16B—C16—H16C	109.5
O4—C9—C8	122.1 (3)
O1—C1—C2—C3	179.3 (3)	O5—C11—C12—C7	179.6 (3)
C14—C1—C2—C3	−1.6 (5)	C10—C11—C12—C7	−1.0 (5)
C1—C2—C3—C4	0.7 (5)	O5—C11—C12—C13	1.2 (5)
C1—C2—C3—C15	−179.2 (3)	C10—C11—C12—C13	−179.5 (3)
C2—C3—C4—C5	0.4 (5)	C8—C7—C12—C11	1.2 (5)
C15—C3—C4—C5	−179.8 (3)	C6—C7—C12—C11	−179.0 (3)
C3—C4—C5—C14	−0.6 (5)	C8—C7—C12—C13	179.7 (3)
C3—C4—C5—C6	177.2 (3)	C6—C7—C12—C13	−0.5 (4)
C4—C5—C6—O3	4.5 (5)	C11—C12—C13—O6	−0.1 (5)
C14—C5—C6—O3	−177.7 (3)	C7—C12—C13—O6	−178.4 (3)
C4—C5—C6—C7	−176.9 (3)	C11—C12—C13—C14	−177.7 (3)
C14—C5—C6—C7	1.0 (4)	C7—C12—C13—C14	3.9 (4)
O3—C6—C7—C8	−3.5 (5)	C4—C5—C14—C1	−0.2 (5)
C5—C6—C7—C8	177.8 (3)	C6—C5—C14—C1	−178.0 (3)
O3—C6—C7—C12	176.7 (3)	C4—C5—C14—C13	−179.6 (3)
C5—C6—C7—C12	−2.0 (4)	C6—C5—C14—C13	2.6 (4)
C12—C7—C8—C9	−2.0 (5)	O1—C1—C14—C5	−179.6 (3)
C6—C7—C8—C9	178.2 (3)	C2—C1—C14—C5	1.3 (5)
C7—C8—C9—O4	−177.9 (3)	O1—C1—C14—C13	−0.2 (4)
C7—C8—C9—C10	2.7 (5)	C2—C1—C14—C13	−179.3 (3)
O4—C9—C10—C11	178.0 (3)	O6—C13—C14—C5	177.2 (3)
C8—C9—C10—C11	−2.5 (5)	C12—C13—C14—C5	−5.1 (4)
C16—O5—C11—C10	−1.2 (4)	O6—C13—C14—C1	−2.2 (4)
C16—O5—C11—C12	178.1 (3)	C12—C13—C14—C1	175.5 (3)
C9—C10—C11—O5	−178.9 (3)	C2—C3—C15—O2	−13.1 (4)
C9—C10—C11—C12	1.7 (5)	C4—C3—C15—O2	167.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.82	1.82	2.525 (3)	144
O2—H2···O5i	0.82	2.38	2.945 (3)	127
O2—H2···O6i	0.82	2.16	2.919 (3)	154
O4—H4···O7ii	0.82	1.85	2.665 (3)	170
O7—H7A···O1	0.85	2.03	2.878 (3)	176
O7—H7B···O2iii	0.85	1.94	2.771 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6	0.82	1.82	2.525 (3)	144
O2—H2⋯O5i	0.82	2.38	2.945 (3)	127
O2—H2⋯O6i	0.82	2.16	2.919 (3)	154
O4—H4⋯O7ii	0.82	1.85	2.665 (3)	170
O7—H7A⋯O1	0.85	2.03	2.878 (3)	176
O7—H7B⋯O2iii	0.85	1.94	2.771 (3)	165

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