9,10-Dioxo-9,10-di-hydro-anthracene-1,4-diyl di-acetate.

In the title compound, C18H12O6, the anthra-quinone ring system is nearly planar [maximum deviation = 0.161 (3) Å] and both acetate groups are located on the same side of the ring plane. A supra-molecular architecture arises in the crystal owing to π-π stacking between parallel benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.883 (4) Å] and weak inter-molecular C-H⋯O hydrogen bonding.

Related literature

For applications of the title compound, see: Mal et al. (2007 ▶). For related compounds, see: Gianneschi et al. (2005 ▶); Thomas (2007 ▶); Lee & Lin (2008 ▶); Han et al. (2009 ▶, 2010 ▶); Lusby (2012 ▶).

Experimental

Crystal data

C18H12O6

M = 324.28

Triclinic,

a = 8.208 (7) Å

b = 9.730 (8) Å

c = 9.902 (8) Å

α = 73.257 (16)°

β = 79.986 (14)°

γ = 80.770 (14)°

V = 740.7 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.978, T max = 0.987

4006 measured reflections

2610 independent reflections

1616 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.01

2610 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010635/xu5688sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010635/xu5688Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010635/xu5688Isup3.cml

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

C18H12O6	Z = 2
Mr = 324.28	F(000) = 336
Triclinic, P1	Dx = 1.454 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.208 (7) Å	Cell parameters from 1029 reflections
b = 9.730 (8) Å	θ = 2.5–25.9°
c = 9.902 (8) Å	µ = 0.11 mm−1
α = 73.257 (16)°	T = 296 K
β = 79.986 (14)°	Block, colorless
γ = 80.770 (14)°	0.20 × 0.15 × 0.12 mm
V = 740.7 (10) Å3

Bruker SMART 1000 CCD area-detector diffractometer	2610 independent reflections
Radiation source: fine-focus sealed tube	1616 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.978, Tmax = 0.987	k = −11→9
4006 measured reflections	l = −8→11

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3
2610 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 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 > 2 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	0.6269 (2)	0.7129 (2)	0.92996 (18)	0.0591 (6)
O2	1.1612 (2)	0.4505 (2)	0.66625 (19)	0.0548 (5)
O3	0.5808 (2)	0.92058 (19)	0.69178 (18)	0.0484 (5)
O4	0.7230 (2)	1.0267 (2)	0.80172 (19)	0.0571 (5)
O5	1.1375 (2)	0.6552 (2)	0.42121 (16)	0.0470 (5)
O6	1.3324 (2)	0.7313 (2)	0.50884 (19)	0.0557 (5)
C1	0.7353 (3)	0.6484 (3)	0.8615 (2)	0.0402 (6)
C2	0.8032 (3)	0.4978 (3)	0.9257 (2)	0.0396 (6)
C3	0.7287 (3)	0.4235 (3)	1.0597 (3)	0.0495 (7)
H3	0.6371	0.4686	1.1067	0.059*
C4	0.7911 (4)	0.2837 (3)	1.1216 (3)	0.0611 (8)
H4	0.7402	0.2340	1.2097	0.073*
C5	0.9294 (4)	0.2166 (3)	1.0533 (3)	0.0622 (8)
H5	0.9717	0.1225	1.0965	0.075*
C6	1.0048 (3)	0.2884 (3)	0.9218 (3)	0.0513 (7)
H6	1.0975	0.2428	0.8765	0.062*
C7	0.9425 (3)	0.4288 (3)	0.8570 (2)	0.0391 (6)
C8	1.0286 (3)	0.5067 (3)	0.7161 (2)	0.0397 (6)
C9	0.9476 (3)	0.6507 (3)	0.6424 (2)	0.0368 (6)
C10	0.8044 (3)	0.7199 (3)	0.7110 (2)	0.0368 (6)
C11	0.7303 (3)	0.8527 (3)	0.6356 (3)	0.0404 (6)
C12	0.7934 (3)	0.9195 (3)	0.4973 (3)	0.0499 (7)
H12	0.7422	1.0084	0.4494	0.060*
C13	0.9328 (3)	0.8533 (3)	0.4309 (3)	0.0499 (7)
H13	0.9762	0.8979	0.3381	0.060*
C14	1.0076 (3)	0.7220 (3)	0.5014 (2)	0.0401 (6)
C15	0.5922 (3)	1.0057 (3)	0.7771 (3)	0.0452 (6)
C16	0.4227 (3)	1.0665 (3)	0.8308 (3)	0.0611 (8)
H16A	0.4327	1.1330	0.8834	0.092*
H16B	0.3629	0.9895	0.8918	0.092*
H16C	0.3634	1.1162	0.7518	0.092*
C17	1.2978 (3)	0.6659 (3)	0.4340 (3)	0.0429 (6)
C18	1.4156 (3)	0.5881 (3)	0.3400 (3)	0.0576 (8)
H18A	1.5278	0.6028	0.3427	0.086*
H18B	1.3903	0.6249	0.2441	0.086*
H18C	1.4044	0.4867	0.3726	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0493 (11)	0.0585 (13)	0.0589 (12)	0.0042 (9)	0.0220 (9)	−0.0221 (10)
O2	0.0333 (10)	0.0549 (12)	0.0680 (12)	0.0058 (9)	0.0123 (8)	−0.0209 (9)
O3	0.0339 (10)	0.0549 (12)	0.0566 (11)	0.0094 (8)	0.0009 (8)	−0.0273 (9)
O4	0.0466 (11)	0.0685 (14)	0.0596 (12)	−0.0058 (10)	0.0038 (9)	−0.0296 (10)
O5	0.0340 (10)	0.0652 (12)	0.0453 (10)	−0.0015 (8)	0.0077 (7)	−0.0302 (9)
O6	0.0452 (11)	0.0624 (13)	0.0653 (12)	−0.0046 (9)	−0.0026 (9)	−0.0298 (10)
C1	0.0283 (12)	0.0511 (16)	0.0434 (14)	−0.0036 (11)	0.0039 (10)	−0.0219 (12)
C2	0.0325 (13)	0.0483 (16)	0.0408 (14)	−0.0068 (11)	−0.0009 (10)	−0.0178 (11)
C3	0.0435 (15)	0.0585 (19)	0.0464 (15)	−0.0107 (13)	0.0052 (11)	−0.0182 (13)
C4	0.066 (2)	0.064 (2)	0.0482 (16)	−0.0156 (16)	0.0012 (14)	−0.0086 (14)
C5	0.065 (2)	0.0511 (19)	0.0637 (19)	−0.0023 (15)	−0.0097 (15)	−0.0069 (14)
C6	0.0441 (15)	0.0508 (18)	0.0564 (17)	0.0030 (13)	−0.0045 (12)	−0.0162 (14)
C7	0.0315 (13)	0.0452 (15)	0.0429 (14)	−0.0041 (11)	−0.0026 (10)	−0.0171 (11)
C8	0.0275 (12)	0.0465 (15)	0.0486 (14)	0.0001 (11)	−0.0018 (10)	−0.0226 (12)
C9	0.0274 (12)	0.0437 (15)	0.0425 (14)	−0.0022 (10)	0.0013 (10)	−0.0213 (11)
C10	0.0284 (12)	0.0454 (15)	0.0397 (13)	−0.0009 (11)	0.0013 (10)	−0.0215 (11)
C11	0.0289 (13)	0.0473 (16)	0.0471 (14)	0.0024 (11)	0.0023 (10)	−0.0240 (12)
C12	0.0510 (16)	0.0488 (16)	0.0455 (15)	0.0042 (13)	−0.0015 (12)	−0.0140 (12)
C13	0.0499 (16)	0.0553 (18)	0.0388 (14)	−0.0027 (13)	0.0054 (11)	−0.0125 (12)
C14	0.0287 (13)	0.0532 (17)	0.0416 (14)	−0.0038 (11)	0.0050 (10)	−0.0238 (12)
C15	0.0437 (16)	0.0456 (16)	0.0422 (14)	0.0037 (13)	0.0030 (11)	−0.0152 (12)
C16	0.0473 (17)	0.067 (2)	0.0661 (19)	0.0093 (15)	0.0079 (13)	−0.0304 (15)
C17	0.0333 (14)	0.0476 (16)	0.0444 (14)	0.0007 (12)	0.0014 (11)	−0.0137 (12)
C18	0.0386 (15)	0.071 (2)	0.0622 (18)	0.0051 (14)	0.0064 (12)	−0.0307 (15)

O1—C1	1.226 (3)	C6—H6	0.9300
O2—C8	1.227 (3)	C7—C8	1.497 (3)
O3—C15	1.365 (3)	C8—C9	1.489 (3)
O3—C11	1.402 (3)	C9—C14	1.409 (3)
O4—C15	1.202 (3)	C9—C10	1.424 (3)
O5—C17	1.366 (3)	C10—C11	1.395 (3)
O5—C14	1.404 (3)	C11—C12	1.384 (4)
O6—C17	1.199 (3)	C12—C13	1.379 (3)
C1—C2	1.478 (4)	C12—H12	0.9300
C1—C10	1.504 (3)	C13—C14	1.371 (4)
C2—C3	1.401 (3)	C13—H13	0.9300
C2—C7	1.403 (3)	C15—C16	1.494 (3)
C3—C4	1.376 (4)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.386 (4)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18	1.494 (3)
C5—C6	1.379 (4)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.387 (3)	C18—H18C	0.9600
C15—O3—C11	117.07 (19)	C9—C10—C1	119.7 (2)
C17—O5—C14	118.35 (18)	C12—C11—C10	121.9 (2)
O1—C1—C2	120.6 (2)	C12—C11—O3	116.2 (2)
O1—C1—C10	121.2 (2)	C10—C11—O3	121.8 (2)
C2—C1—C10	118.13 (19)	C13—C12—C11	119.5 (3)
C3—C2—C7	119.3 (2)	C13—C12—H12	120.3
C3—C2—C1	119.2 (2)	C11—C12—H12	120.3
C7—C2—C1	121.5 (2)	C14—C13—C12	120.1 (2)
C4—C3—C2	120.0 (2)	C14—C13—H13	119.9
C4—C3—H3	120.0	C12—C13—H13	119.9
C2—C3—H3	120.0	C13—C14—O5	116.3 (2)
C3—C4—C5	120.4 (3)	C13—C14—C9	122.1 (2)
C3—C4—H4	119.8	O5—C14—C9	121.3 (2)
C5—C4—H4	119.8	O4—C15—O3	122.9 (2)
C6—C5—C4	120.4 (3)	O4—C15—C16	126.7 (2)
C6—C5—H5	119.8	O3—C15—C16	110.3 (2)
C4—C5—H5	119.8	C15—C16—H16A	109.5
C5—C6—C7	120.0 (2)	C15—C16—H16B	109.5
C5—C6—H6	120.0	H16A—C16—H16B	109.5
C7—C6—H6	120.0	C15—C16—H16C	109.5
C6—C7—C2	119.9 (2)	H16A—C16—H16C	109.5
C6—C7—C8	119.3 (2)	H16B—C16—H16C	109.5
C2—C7—C8	120.7 (2)	O6—C17—O5	123.0 (2)
O2—C8—C9	122.9 (2)	O6—C17—C18	127.4 (2)
O2—C8—C7	119.4 (2)	O5—C17—C18	109.6 (2)
C9—C8—C7	117.76 (19)	C17—C18—H18A	109.5
C14—C9—C10	117.6 (2)	C17—C18—H18B	109.5
C14—C9—C8	121.31 (19)	H18A—C18—H18B	109.5
C10—C9—C8	121.1 (2)	C17—C18—H18C	109.5
C11—C10—C9	118.8 (2)	H18A—C18—H18C	109.5
C11—C10—C1	121.5 (2)	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O2i	0.96	2.51	3.425 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O2i	0.96	2.51	3.425 (4)	159

Symmetry code: (i) .