6,11-Dihydroxy-naphthacene-5,12-dione.

The mol-ecule of the title compound, C(18)H(10)O(4), is centrosymmetric and planar. A long phenolic O-H bond is observed [1.19 (9) Å], which is involved in an intra-molecular hydrogen bond between the phenolic and quinonoid O atoms. The mol-ecules pack in a herringbone pattern and are linked to each other via inter-molecular C-H⋯O hydrogen bonds (2.73-2.77 Å).

Related literature

The crystal structure of the rhenium complex including the title compound has been reported (Sathiyendiran et al., 2007 ▶). For studies of naphthaza­rin (5,8-dihydr­oxy-1,4-naphtho­quinone), see: Fehlmann & Nigli (1965 ▶); Cradwick & Hall (1971 ▶); Herbstein et al. (1985 ▶); Rubio et al. (1985 ▶); Sarkhel et al. (2001 ▶); Savko et al. (2007 ▶). For background on intra­molecular hydrogen bonds, see: Gilli et al. (1989 ▶); Bertolasi et al. (1991 ▶); Gilli et al. (1993 ▶); Steiner & Saenger (1994 ▶). For background on inter­molecular hydrogen bonds, see: Taylor & Kennard (1982 ▶); Jagarlapudi & Desiraju (1987 ▶); Biradha et al. (1993 ▶); Batchelor et al. (2000 ▶). For background on resonance structures, see: Cradwick & Hall (1971 ▶); Shiau et al. (1980 ▶).

Experimental

Crystal data

C18H10O4

M = 290.26

Monoclinic,

a = 8.85 (2) Å

b = 3.750 (8) Å

c = 18.74 (4) Å

β = 94.55 (3)°

V = 620 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 173 (2) K

0.29 × 0.07 × 0.03 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: none

5026 measured reflections

1347 independent reflections

668 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.114

wR(F 2) = 0.354

S = 0.99

1347 reflections

104 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063726/gw2022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063726/gw2022Isup2.hkl

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

C18H10O4	F(000) = 300
Mr = 290.26	Dx = 1.555 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 928 reflections
a = 8.85 (2) Å	θ = 3.1–27.5°
b = 3.750 (8) Å	µ = 0.11 mm−1
c = 18.74 (4) Å	T = 173 K
β = 94.55 (3)°	Prism, red
V = 620 (2) Å3	0.29 × 0.07 × 0.03 mm
Z = 2

Rigaku Mercury CCD diffractometer	668 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.087
Graphite Monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 14.6199 pixels mm-1	h = −9→11
φ and ω scans	k = −4→3
5026 measured reflections	l = −19→24
1347 independent reflections

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)] = 0.114	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.354	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.1532P)2 + 1.2875P] where P = (Fo2 + 2Fc2)/3
1347 reflections	(Δ/σ)max = 0.053
104 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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	0.3137 (5)	0.1246 (12)	0.4518 (2)	0.0438 (12)
O2	0.1298 (5)	−0.1563 (12)	0.3591 (2)	0.0426 (12)
H2	0.248 (10)	−0.03 (3)	0.378 (5)	0.09 (3)*
C1	0.2384 (6)	0.2682 (14)	0.5696 (3)	0.0317 (13)
C2	0.1249 (6)	0.2760 (13)	0.6171 (3)	0.0290 (12)
C3	0.1583 (7)	0.4134 (15)	0.6871 (3)	0.0363 (14)
H3	0.0823	0.4198	0.7201	0.044*
C4	0.3022 (7)	0.5375 (15)	0.7068 (3)	0.0381 (15)
H4	0.3247	0.6318	0.7535	0.046*
C5	0.4162 (7)	0.5264 (15)	0.6586 (3)	0.0403 (15)
H5	0.5151	0.6117	0.6728	0.048*
C6	0.3839 (7)	0.3917 (14)	0.5910 (3)	0.0371 (14)
H6	0.4611	0.3823	0.5586	0.045*
C7	0.2079 (6)	0.1277 (14)	0.4965 (3)	0.0294 (12)
C8	0.0599 (6)	−0.0051 (14)	0.4744 (3)	0.0312 (13)
C9	0.0278 (7)	−0.1452 (13)	0.4050 (3)	0.0308 (13)

	U11	U22	U33	U12	U13	U23
O1	0.034 (2)	0.052 (3)	0.046 (3)	−0.011 (2)	0.0070 (18)	−0.004 (2)
O2	0.042 (3)	0.048 (3)	0.041 (2)	0.000 (2)	0.0186 (19)	−0.0051 (19)
C1	0.027 (3)	0.025 (3)	0.043 (3)	0.003 (2)	0.002 (2)	−0.001 (2)
C2	0.028 (3)	0.024 (3)	0.034 (3)	0.000 (2)	−0.005 (2)	0.001 (2)
C3	0.049 (4)	0.028 (3)	0.031 (3)	−0.005 (3)	−0.003 (2)	0.004 (2)
C4	0.063 (4)	0.027 (3)	0.023 (3)	−0.001 (3)	−0.008 (3)	0.000 (2)
C5	0.042 (3)	0.031 (3)	0.045 (3)	−0.001 (3)	−0.011 (3)	0.002 (3)
C6	0.038 (3)	0.022 (3)	0.052 (4)	−0.004 (2)	0.004 (3)	0.005 (2)
C7	0.021 (3)	0.030 (3)	0.037 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C8	0.036 (3)	0.031 (3)	0.025 (3)	0.001 (2)	−0.006 (2)	0.012 (2)
C9	0.044 (3)	0.021 (2)	0.028 (3)	−0.002 (2)	0.002 (2)	−0.002 (2)

O1—C7	1.304 (6)	C4—C5	1.407 (9)
O2—C9	1.296 (7)	C4—H4	0.9500
O2—H2	1.19 (9)	C5—C6	1.373 (8)
C1—C2	1.395 (8)	C5—H5	0.9500
C1—C6	1.398 (8)	C6—H6	0.9500
C1—C7	1.472 (8)	C7—C8	1.432 (8)
C2—C3	1.418 (8)	C8—C9	1.410 (7)
C2—C9i	1.467 (8)	C8—C8i	1.486 (11)
C3—C4	1.378 (9)	C9—C2i	1.467 (8)
C3—H3	0.9500
C7—O1—H2	110 (3)	C6—C5—H5	120.1
C9—O2—H2	115 (4)	C4—C5—H5	120.1
C2—C1—C6	120.2 (5)	C5—C6—C1	120.4 (6)
C2—C1—C7	120.9 (5)	C5—C6—H6	119.8
C6—C1—C7	118.9 (5)	C1—C6—H6	119.8
C1—C2—C3	119.4 (5)	O1—C7—C8	119.9 (5)
C1—C2—C9i	120.4 (5)	O1—C7—C1	120.8 (5)
C3—C2—C9i	120.2 (5)	C8—C7—C1	119.3 (5)
C2—C3—C4	119.4 (5)	C9—C8—C7	120.6 (5)
C2—C3—H3	120.3	C9—C8—C8i	120.2 (6)
C4—C3—H3	120.3	C7—C8—C8i	119.2 (6)
C3—C4—C5	120.8 (5)	O2—C9—C8	121.6 (5)
C3—C4—H4	119.6	O2—C9—C2i	118.4 (5)
C5—C4—H4	119.6	C8—C9—C2i	119.9 (5)
C6—C5—C4	119.7 (6)
C6—C1—C2—C3	0.6 (8)	C6—C1—C7—O1	−1.4 (8)
C7—C1—C2—C3	−180.0 (5)	C2—C1—C7—C8	−0.5 (8)
C6—C1—C2—C9i	−179.7 (5)	C6—C1—C7—C8	178.9 (5)
C7—C1—C2—C9i	−0.3 (8)	O1—C7—C8—C9	1.1 (7)
C1—C2—C3—C4	0.2 (7)	C1—C7—C8—C9	−179.3 (5)
C9i—C2—C3—C4	−179.5 (5)	O1—C7—C8—C8i	−179.1 (6)
C2—C3—C4—C5	−0.6 (8)	C1—C7—C8—C8i	0.6 (8)
C3—C4—C5—C6	0.3 (8)	C7—C8—C9—O2	−0.5 (8)
C4—C5—C6—C1	0.5 (8)	C8i—C8—C9—O2	179.7 (6)
C2—C1—C6—C5	−0.9 (8)	C7—C8—C9—C2i	−179.2 (5)
C7—C1—C6—C5	179.6 (5)	C8i—C8—C9—C2i	1.0 (8)
C2—C1—C7—O1	179.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	1.19 (9)	1.56 (9)	2.516 (7)	132 (6)
C6—H6···O1ii	0.95	2.77	3.449 (9)	129
C6—H6···O1iii	0.95	2.74	3.382 (9)	126
C3—H3···O2iv	0.95	2.75	3.378 (10)	124
C4—H4···O2iv	0.95	2.73	3.371 (9)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	1.19 (9)	1.56 (9)	2.516 (7)	132 (6)
C6—H6⋯O1i	0.95	2.77	3.449 (9)	129
C6—H6⋯O1ii	0.95	2.74	3.382 (9)	126
C3—H3⋯O2iii	0.95	2.75	3.378 (10)	124
C4—H4⋯O2iii	0.95	2.73	3.371 (9)	126

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