4-(9,10-Dioxo-9,10-dihydro-anthracen-1-yl)-4-oxobutanoic acid.

In the title compound, C(18)H(12)O(5), the anthracene moiety is almost planar (r.m.s. deviation = 0.0399 Å). In the crystal, mol-ecules are linked to each other by inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For applications of natural and synthetic anthraquinones, see: Brown (1980 ▶). For their activity, see: Johnson et al. (1997 ▶). For the synthesis, see: Inbasekaran et al. (1980 ▶).

Experimental

Crystal data

C18H12O5

M = 308.28

Monoclinic,

a = 5.168 (1) Å

b = 19.523 (4) Å

c = 14.367 (3) Å

β = 99.58 (3)°

V = 1429.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.979, T max = 0.990

2892 measured reflections

2593 independent reflections

1048 reflections with I > 2σ(I)

R int = 0.077

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.161

S = 1.00

2593 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004732X/bq2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004732X/bq2254Isup2.hkl

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

C18H12O5	F(000) = 640
Mr = 308.28	Dx = 1.433 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 5.168 (1) Å	θ = 8–12°
b = 19.523 (4) Å	µ = 0.11 mm−1
c = 14.367 (3) Å	T = 293 K
β = 99.58 (3)°	Needle, colourless
V = 1429.3 (5) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1048 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.077
graphite	θmax = 25.3°, θmin = 1.8°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
Tmin = 0.979, Tmax = 0.990	l = −17→17
2892 measured reflections	3 standard reflections every 200 reflections
2593 independent reflections	intensity decay: 1%

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
2593 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 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	0.6562 (8)	0.45510 (18)	0.4314 (3)	0.0687 (12)
O2	0.2523 (6)	0.26823 (17)	0.6393 (2)	0.0534 (10)
O3	−0.2936 (7)	0.21707 (19)	0.5131 (3)	0.0722 (13)
O4	−0.2825 (7)	0.04974 (17)	0.4635 (3)	0.0580 (11)
O5	−0.3291 (8)	0.0347 (2)	0.6115 (3)	0.0796 (13)
H5A	−0.4460	0.0090	0.5866	0.119*
C1	−0.0859 (11)	0.2918 (3)	0.3566 (4)	0.0590 (16)
H1A	−0.2305	0.2662	0.3293	0.071*
C2	0.0084 (12)	0.3422 (3)	0.3052 (4)	0.0656 (17)
H2A	−0.0687	0.3499	0.2429	0.079*
C3	0.2165 (11)	0.3814 (3)	0.3457 (4)	0.0556 (15)
H3A	0.2776	0.4161	0.3107	0.067*
C4	0.3375 (10)	0.3703 (2)	0.4378 (4)	0.0412 (13)
C5	0.5697 (10)	0.4127 (3)	0.4790 (4)	0.0467 (14)
C6	0.6852 (10)	0.4001 (2)	0.5783 (3)	0.0408 (13)
C7	0.9026 (11)	0.4383 (3)	0.6188 (4)	0.0555 (15)
H7A	0.9726	0.4712	0.5832	0.067*
C8	1.0149 (11)	0.4274 (3)	0.7122 (4)	0.0611 (17)
H8A	1.1575	0.4537	0.7397	0.073*
C9	0.9160 (11)	0.3780 (3)	0.7640 (4)	0.0640 (17)
H9A	0.9928	0.3702	0.8264	0.077*
C10	0.7023 (10)	0.3397 (3)	0.7236 (4)	0.0548 (15)
H10A	0.6372	0.3060	0.7593	0.066*
C11	0.5839 (9)	0.3501 (2)	0.6323 (4)	0.0425 (13)
C12	0.3528 (10)	0.3090 (2)	0.5912 (4)	0.0425 (13)
C13	0.2415 (9)	0.3191 (2)	0.4900 (3)	0.0365 (12)
C14	0.0322 (9)	0.2783 (2)	0.4497 (3)	0.0392 (12)
C15	−0.0699 (10)	0.2173 (3)	0.4968 (4)	0.0484 (14)
C16	0.0972 (9)	0.1546 (2)	0.5123 (4)	0.0502 (14)
H16A	0.2779	0.1679	0.5340	0.060*
H16B	0.0898	0.1305	0.4529	0.060*
C17	0.0093 (10)	0.1069 (2)	0.5841 (4)	0.0526 (15)
H17A	0.1567	0.0784	0.6109	0.063*
H17B	−0.0394	0.1343	0.6348	0.063*
C18	−0.2128 (10)	0.0622 (2)	0.5464 (4)	0.0493 (14)

	U11	U22	U33	U12	U13	U23
O1	0.081 (3)	0.059 (3)	0.071 (3)	−0.018 (2)	0.029 (2)	0.018 (2)
O2	0.061 (3)	0.053 (2)	0.048 (2)	−0.0200 (19)	0.012 (2)	0.0045 (18)
O3	0.035 (2)	0.068 (3)	0.119 (4)	−0.007 (2)	0.027 (2)	−0.005 (2)
O4	0.060 (3)	0.061 (2)	0.049 (2)	−0.026 (2)	−0.003 (2)	0.0015 (19)
O5	0.088 (3)	0.086 (3)	0.067 (3)	−0.036 (3)	0.021 (2)	−0.005 (2)
C1	0.049 (4)	0.060 (4)	0.065 (4)	0.000 (3)	0.001 (3)	−0.015 (3)
C2	0.077 (5)	0.069 (4)	0.044 (4)	0.003 (4)	−0.006 (3)	−0.002 (3)
C3	0.072 (4)	0.051 (4)	0.046 (4)	0.000 (3)	0.018 (3)	0.007 (3)
C4	0.043 (3)	0.041 (3)	0.041 (3)	−0.004 (3)	0.011 (3)	0.003 (2)
C5	0.054 (4)	0.038 (3)	0.052 (4)	0.000 (3)	0.019 (3)	0.002 (3)
C6	0.045 (3)	0.030 (3)	0.050 (3)	−0.004 (3)	0.014 (3)	−0.005 (3)
C7	0.053 (4)	0.046 (3)	0.073 (4)	−0.006 (3)	0.025 (3)	−0.014 (3)
C8	0.051 (4)	0.062 (4)	0.069 (4)	−0.005 (3)	0.006 (3)	−0.019 (3)
C9	0.070 (4)	0.068 (4)	0.051 (4)	−0.012 (4)	0.002 (3)	−0.011 (3)
C10	0.054 (4)	0.062 (4)	0.046 (4)	−0.010 (3)	0.000 (3)	−0.005 (3)
C11	0.038 (3)	0.039 (3)	0.050 (3)	0.002 (3)	0.006 (3)	−0.009 (3)
C12	0.041 (3)	0.037 (3)	0.052 (4)	−0.002 (3)	0.013 (3)	−0.003 (3)
C13	0.031 (3)	0.041 (3)	0.038 (3)	0.003 (2)	0.008 (2)	−0.009 (3)
C14	0.031 (3)	0.039 (3)	0.047 (3)	0.005 (3)	0.001 (3)	−0.006 (3)
C15	0.039 (3)	0.039 (3)	0.067 (4)	−0.003 (3)	0.008 (3)	−0.009 (3)
C16	0.038 (3)	0.044 (3)	0.071 (4)	−0.009 (3)	0.016 (3)	−0.013 (3)
C17	0.051 (3)	0.038 (3)	0.068 (4)	−0.007 (3)	0.008 (3)	−0.006 (3)
C18	0.048 (4)	0.038 (3)	0.061 (4)	−0.010 (3)	0.007 (3)	0.004 (3)

O1—C5	1.206 (5)	C7—H7A	0.9300
O2—C12	1.225 (5)	C8—C9	1.368 (7)
O3—C15	1.218 (5)	C8—H8A	0.9300
O4—C18	1.210 (6)	C9—C10	1.379 (6)
O5—C18	1.308 (6)	C9—H9A	0.9300
O5—H5A	0.8200	C10—C11	1.367 (6)
C1—C2	1.367 (7)	C10—H10A	0.9300
C1—C14	1.400 (6)	C11—C12	1.478 (6)
C1—H1A	0.9300	C12—C13	1.484 (6)
C2—C3	1.368 (7)	C13—C14	1.389 (6)
C2—H2A	0.9300	C14—C15	1.508 (6)
C3—C4	1.383 (6)	C15—C16	1.494 (6)
C3—H3A	0.9300	C16—C17	1.513 (6)
C4—C13	1.391 (6)	C16—H16A	0.9700
C4—C5	1.496 (6)	C16—H16B	0.9700
C5—C6	1.472 (6)	C17—C18	1.472 (6)
C6—C7	1.393 (6)	C17—H17A	0.9700
C6—C11	1.402 (6)	C17—H17B	0.9700
C7—C8	1.388 (7)
C18—O5—H5A	109.5	C10—C11—C6	119.1 (5)
C2—C1—C14	120.8 (5)	C10—C11—C12	120.4 (5)
C2—C1—H1A	119.6	C6—C11—C12	120.5 (5)
C14—C1—H1A	119.6	O2—C12—C11	121.1 (5)
C1—C2—C3	119.9 (5)	O2—C12—C13	120.5 (5)
C1—C2—H2A	120.0	C11—C12—C13	118.4 (4)
C3—C2—H2A	120.0	C14—C13—C4	120.7 (5)
C2—C3—C4	121.2 (5)	C14—C13—C12	118.7 (5)
C2—C3—H3A	119.4	C4—C13—C12	120.6 (5)
C4—C3—H3A	119.4	C13—C14—C1	118.4 (5)
C3—C4—C13	118.9 (5)	C13—C14—C15	124.9 (5)
C3—C4—C5	119.8 (5)	C1—C14—C15	116.6 (5)
C13—C4—C5	121.3 (5)	O3—C15—C16	120.8 (5)
O1—C5—C6	122.4 (5)	O3—C15—C14	120.3 (5)
O1—C5—C4	120.2 (5)	C16—C15—C14	118.6 (4)
C6—C5—C4	117.4 (5)	C15—C16—C17	112.0 (4)
C7—C6—C11	119.4 (5)	C15—C16—H16A	109.2
C7—C6—C5	118.9 (5)	C17—C16—H16A	109.2
C11—C6—C5	121.6 (5)	C15—C16—H16B	109.2
C8—C7—C6	120.0 (5)	C17—C16—H16B	109.2
C8—C7—H7A	120.0	H16A—C16—H16B	107.9
C6—C7—H7A	120.0	C18—C17—C16	114.8 (5)
C9—C8—C7	120.1 (6)	C18—C17—H17A	108.6
C9—C8—H8A	120.0	C16—C17—H17A	108.6
C7—C8—H8A	120.0	C18—C17—H17B	108.6
C8—C9—C10	119.9 (6)	C16—C17—H17B	108.6
C8—C9—H9A	120.1	H17A—C17—H17B	107.6
C10—C9—H9A	120.1	O4—C18—O5	121.6 (5)
C11—C10—C9	121.5 (6)	O4—C18—C17	124.5 (5)
C11—C10—H10A	119.2	O5—C18—C17	113.8 (5)
C9—C10—H10A	119.2
C14—C1—C2—C3	−1.8 (8)	C10—C11—C12—C13	−176.1 (4)
C1—C2—C3—C4	1.1 (8)	C6—C11—C12—C13	3.6 (6)
C2—C3—C4—C13	−1.2 (8)	C3—C4—C13—C14	1.8 (7)
C2—C3—C4—C5	178.2 (5)	C5—C4—C13—C14	−177.5 (4)
C3—C4—C5—O1	−2.2 (7)	C3—C4—C13—C12	−175.4 (4)
C13—C4—C5—O1	177.1 (5)	C5—C4—C13—C12	5.3 (7)
C3—C4—C5—C6	178.1 (4)	O2—C12—C13—C14	−4.1 (7)
C13—C4—C5—C6	−2.6 (7)	C11—C12—C13—C14	177.0 (4)
O1—C5—C6—C7	−0.1 (7)	O2—C12—C13—C4	173.2 (4)
C4—C5—C6—C7	179.6 (4)	C11—C12—C13—C4	−5.8 (6)
O1—C5—C6—C11	−179.3 (5)	C4—C13—C14—C1	−2.5 (7)
C4—C5—C6—C11	0.4 (7)	C12—C13—C14—C1	174.8 (4)
C11—C6—C7—C8	−0.8 (7)	C4—C13—C14—C15	173.8 (4)
C5—C6—C7—C8	180.0 (5)	C12—C13—C14—C15	−8.9 (7)
C6—C7—C8—C9	1.5 (8)	C2—C1—C14—C13	2.4 (7)
C7—C8—C9—C10	−0.9 (8)	C2—C1—C14—C15	−174.2 (5)
C8—C9—C10—C11	−0.4 (8)	C13—C14—C15—O3	118.0 (6)
C9—C10—C11—C6	1.1 (8)	C1—C14—C15—O3	−65.7 (7)
C9—C10—C11—C12	−179.2 (5)	C13—C14—C15—C16	−69.1 (6)
C7—C6—C11—C10	−0.4 (7)	C1—C14—C15—C16	107.2 (5)
C5—C6—C11—C10	178.7 (5)	O3—C15—C16—C17	−24.0 (7)
C7—C6—C11—C12	179.8 (4)	C14—C15—C16—C17	163.1 (4)
C5—C6—C11—C12	−1.1 (7)	C15—C16—C17—C18	81.7 (5)
C10—C11—C12—O2	4.9 (7)	C16—C17—C18—O4	18.2 (7)
C6—C11—C12—O2	−175.3 (4)	C16—C17—C18—O5	−163.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4i	0.82	1.86	2.681 (6)	177
C7—H7A···O1ii	0.93	2.43	3.255 (7)	147
C16—H16A···O3iii	0.97	2.48	3.375 (6)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4i	0.82	1.86	2.681 (6)	177
C7—H7A⋯O1ii	0.93	2.43	3.255 (7)	147
C16—H16A⋯O3iii	0.97	2.48	3.375 (6)	154

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