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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Page o788
https://doi.org/10.1107/S1600536813010635

9,10-Dioxo-9,10-di­hydro­anthracene-1,4-diyl di­acetate

Jing-Jing Zhang,a Cai-Xia Yina* and Fang-Jun Huob

aInstitute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of Education Ministry, University of Shanxi, Taiyuan, Shanxi 030006, People's Republic of China, and bResearch Institute of Applied Chemistry, University of Shanxi, Taiyuan, Shanxi 030006, People's Republic of China
*Correspondence e-mail: yincx@sxu.edu.cn

(Received 12 March 2013; accepted 18 April 2013; online 27 April 2013)

In the title compound, C18H12O6, the anthra­quinone 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 supra­molecular architecture arises in the crystal owing to π–π stacking between parallel benzene rings of adjacent mol­ecules [centroid–centroid distance = 3.883 (4) Å] and weak inter­molecular C—H⋯O hydrogen bonding.

Related literature

For applications of the title compound, see: Mal et al. (2007[Mal, D., Ray, S. & Sharma, I. J. (2007). J. Org. Chem. 72, 4981-4984.]). For related compounds, see: Gianneschi et al. (2005[Gianneschi, N. C., Masar, M. S. & Mirkin, C. A. (2005). Acc. Chem. Res. 38, 825-837.]); Thomas (2007[Thomas, J. A. (2007). Chem. Soc. Rev. 36, 856-868.]); Lee & Lin (2008[Lee, S. J. & Lin, W. (2008). Acc. Chem. Res. 41, 521-537.]); Han et al. (2009[Han, Y.-F., Jia, W.-G., Yu, W.-B. & Jin, G.-X. (2009). Chem. Soc. Rev. 38, 3419-3434.], 2010[Han, Y.-F., Li, H. & Jin, G.-X. (2010). Chem. Commun. 46, 6879-6890.]); Lusby (2012[Lusby, P. J. (2012). Inorg. Chem. 108, 292-314.]).

[Scheme 1]

Experimental

Crystal data

  • C18H12O6

  • Mr = 324.28

  • Triclinic, [P \overline 1]

  • 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.987

  • 4006 measured reflections

  • 2610 independent reflections

  • 1616 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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

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) -x+3, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813010635/xu5688sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010635/xu5688Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010635/xu5688Isup3.cml

checkCIF report


Comment top

The title compound has symmetry space structure and obvious color. It can be used to synthesize various dyes and are common structural subunits of many biologically active quinonoids (Mal et al., 2007). It also can be modified into synthetic dyes intermediates, 1,4-diamino anthraquinone. Its readily deprotection of acetate groups forms 1,4-dihydroxyanthraquinone (1,4-DHA), which can be induced to self-assembly to form a metallo-supramolecular coordination polymers under certain condition (Gianneschi et al., 2005; Thomas, 2007; Lee & Lin, 2008) and demonstrate good selectivity and binding for planar aromatic guests, small organic molecules and transitional metal ions, such as dichloromethane and iridium (Han et al., 2009; Lusby, 2012; Han et al., 2010)

The molecular conformation is illustrated in Fig. 1. In the title compound, C18H12O6, the anthraquinone ring system is nearly planar [the maximum deviation being 0.161 (3) Å], both acetate groups are located on the same side of the ring plane. A three-dimensional supramolecular architecture arises in the crystal owing to π-π stacking between centro-symmetrically related benzene rings [centroid-centroid distance 3.883 (4) Å] and weak intermolecular C—H···O hydrogen bondig.

Related literature top

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 top

To a stirred solution of 1,4-dihydrory-9,10-anthraquinone (4.6 g, 19.1 mmoL) in CH2Cl2 (50 ml), Ac2O (2 ml) and pyridine (one drop) were added. After the solution was stirred overnight at room temperature, it was evaporated under vacuum. The crude products were dissolved in water and then extracted with EtOAc. The combinded organic layer was washed with brine, and then dried with Na2SO4. The solvent was removed under the reduced pressure and the residue was purified by column chromatography using petroleum ether/ethyl acetate (v/v 2:1, Rf = 0.50) as an eluent to afford 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate as a white solid. Colorless single crystals were obtained from the ethyl acetate solution.

Refinement top

All H atoms were initially lacated in a difference Fourier map. H atoms on Csp3 were treated as riding with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) of the parent atom. The H atoms on Csp2 were treated as riding with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

The title compound has symmetry space structure and obvious color. It can be used to synthesize various dyes and are common structural subunits of many biologically active quinonoids (Mal et al., 2007). It also can be modified into synthetic dyes intermediates, 1,4-diamino anthraquinone. Its readily deprotection of acetate groups forms 1,4-dihydroxyanthraquinone (1,4-DHA), which can be induced to self-assembly to form a metallo-supramolecular coordination polymers under certain condition (Gianneschi et al., 2005; Thomas, 2007; Lee & Lin, 2008) and demonstrate good selectivity and binding for planar aromatic guests, small organic molecules and transitional metal ions, such as dichloromethane and iridium (Han et al., 2009; Lusby, 2012; Han et al., 2010)

The molecular conformation is illustrated in Fig. 1. In the title compound, C18H12O6, the anthraquinone ring system is nearly planar [the maximum deviation being 0.161 (3) Å], both acetate groups are located on the same side of the ring plane. A three-dimensional supramolecular architecture arises in the crystal owing to π-π stacking between centro-symmetrically related benzene rings [centroid-centroid distance 3.883 (4) Å] and weak intermolecular C—H···O hydrogen bondig.

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).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I) with the atom-numbering scheme.
9,10-Dioxo-9,10-dihydroanthracene-1,4-diyl diacetate top
Crystal data top
C18H12O6Z = 2
Mr = 324.28F(000) = 336
Triclinic, P1Dx = 1.454 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.208 (7) ÅCell parameters from 1029 reflections
b = 9.730 (8) Åθ = 2.5–25.9°
c = 9.902 (8) ŵ = 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
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2610 independent reflections
Radiation source: fine-focus sealed tube1616 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −9→9
Tmin = 0.978, Tmax = 0.987k = −11→9
4006 measured reflectionsl = −8→11
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-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 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C18H12O6γ = 80.770 (14)°
Mr = 324.28V = 740.7 (10) Å3
Triclinic, P1Z = 2
a = 8.208 (7) ÅMo Kα radiation
b = 9.730 (8) ŵ = 0.11 mm−1
c = 9.902 (8) ÅT = 296 K
α = 73.257 (16)°0.20 × 0.15 × 0.12 mm
β = 79.986 (14)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2610 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1616 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.987Rint = 0.023
4006 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.01Δρmax = 0.25 e Å−3
2610 reflectionsΔρmin = −0.20 e Å−3
219 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6269 (2)0.7129 (2)0.92996 (18)0.0591 (6)
O21.1612 (2)0.4505 (2)0.66625 (19)0.0548 (5)
O30.5808 (2)0.92058 (19)0.69178 (18)0.0484 (5)
O40.7230 (2)1.0267 (2)0.80172 (19)0.0571 (5)
O51.1375 (2)0.6552 (2)0.42121 (16)0.0470 (5)
O61.3324 (2)0.7313 (2)0.50884 (19)0.0557 (5)
C10.7353 (3)0.6484 (3)0.8615 (2)0.0402 (6)
C20.8032 (3)0.4978 (3)0.9257 (2)0.0396 (6)
C30.7287 (3)0.4235 (3)1.0597 (3)0.0495 (7)
H30.63710.46861.10670.059*
C40.7911 (4)0.2837 (3)1.1216 (3)0.0611 (8)
H40.74020.23401.20970.073*
C50.9294 (4)0.2166 (3)1.0533 (3)0.0622 (8)
H50.97170.12251.09650.075*
C61.0048 (3)0.2884 (3)0.9218 (3)0.0513 (7)
H61.09750.24280.87650.062*
C70.9425 (3)0.4288 (3)0.8570 (2)0.0391 (6)
C81.0286 (3)0.5067 (3)0.7161 (2)0.0397 (6)
C90.9476 (3)0.6507 (3)0.6424 (2)0.0368 (6)
C100.8044 (3)0.7199 (3)0.7110 (2)0.0368 (6)
C110.7303 (3)0.8527 (3)0.6356 (3)0.0404 (6)
C120.7934 (3)0.9195 (3)0.4973 (3)0.0499 (7)
H120.74221.00840.44940.060*
C130.9328 (3)0.8533 (3)0.4309 (3)0.0499 (7)
H130.97620.89790.33810.060*
C141.0076 (3)0.7220 (3)0.5014 (2)0.0401 (6)
C150.5922 (3)1.0057 (3)0.7771 (3)0.0452 (6)
C160.4227 (3)1.0665 (3)0.8308 (3)0.0611 (8)
H16A0.43271.13300.88340.092*
H16B0.36290.98950.89180.092*
H16C0.36341.11620.75180.092*
C171.2978 (3)0.6659 (3)0.4340 (3)0.0429 (6)
C181.4156 (3)0.5881 (3)0.3400 (3)0.0576 (8)
H18A1.52780.60280.34270.086*
H18B1.39030.62490.24410.086*
H18C1.40440.48670.37260.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0493 (11)0.0585 (13)0.0589 (12)0.0042 (9)0.0220 (9)−0.0221 (10)
O20.0333 (10)0.0549 (12)0.0680 (12)0.0058 (9)0.0123 (8)−0.0209 (9)
O30.0339 (10)0.0549 (12)0.0566 (11)0.0094 (8)0.0009 (8)−0.0273 (9)
O40.0466 (11)0.0685 (14)0.0596 (12)−0.0058 (10)0.0038 (9)−0.0296 (10)
O50.0340 (10)0.0652 (12)0.0453 (10)−0.0015 (8)0.0077 (7)−0.0302 (9)
O60.0452 (11)0.0624 (13)0.0653 (12)−0.0046 (9)−0.0026 (9)−0.0298 (10)
C10.0283 (12)0.0511 (16)0.0434 (14)−0.0036 (11)0.0039 (10)−0.0219 (12)
C20.0325 (13)0.0483 (16)0.0408 (14)−0.0068 (11)−0.0009 (10)−0.0178 (11)
C30.0435 (15)0.0585 (19)0.0464 (15)−0.0107 (13)0.0052 (11)−0.0182 (13)
C40.066 (2)0.064 (2)0.0482 (16)−0.0156 (16)0.0012 (14)−0.0086 (14)
C50.065 (2)0.0511 (19)0.0637 (19)−0.0023 (15)−0.0097 (15)−0.0069 (14)
C60.0441 (15)0.0508 (18)0.0564 (17)0.0030 (13)−0.0045 (12)−0.0162 (14)
C70.0315 (13)0.0452 (15)0.0429 (14)−0.0041 (11)−0.0026 (10)−0.0171 (11)
C80.0275 (12)0.0465 (15)0.0486 (14)0.0001 (11)−0.0018 (10)−0.0226 (12)
C90.0274 (12)0.0437 (15)0.0425 (14)−0.0022 (10)0.0013 (10)−0.0213 (11)
C100.0284 (12)0.0454 (15)0.0397 (13)−0.0009 (11)0.0013 (10)−0.0215 (11)
C110.0289 (13)0.0473 (16)0.0471 (14)0.0024 (11)0.0023 (10)−0.0240 (12)
C120.0510 (16)0.0488 (16)0.0455 (15)0.0042 (13)−0.0015 (12)−0.0140 (12)
C130.0499 (16)0.0553 (18)0.0388 (14)−0.0027 (13)0.0054 (11)−0.0125 (12)
C140.0287 (13)0.0532 (17)0.0416 (14)−0.0038 (11)0.0050 (10)−0.0238 (12)
C150.0437 (16)0.0456 (16)0.0422 (14)0.0037 (13)0.0030 (11)−0.0152 (12)
C160.0473 (17)0.067 (2)0.0661 (19)0.0093 (15)0.0079 (13)−0.0304 (15)
C170.0333 (14)0.0476 (16)0.0444 (14)0.0007 (12)0.0014 (11)−0.0137 (12)
C180.0386 (15)0.071 (2)0.0622 (18)0.0051 (14)0.0064 (12)−0.0307 (15)
Geometric parameters (Å, º) top
O1—C11.226 (3)C6—H60.9300
O2—C81.227 (3)C7—C81.497 (3)
O3—C151.365 (3)C8—C91.489 (3)
O3—C111.402 (3)C9—C141.409 (3)
O4—C151.202 (3)C9—C101.424 (3)
O5—C171.366 (3)C10—C111.395 (3)
O5—C141.404 (3)C11—C121.384 (4)
O6—C171.199 (3)C12—C131.379 (3)
C1—C21.478 (4)C12—H120.9300
C1—C101.504 (3)C13—C141.371 (4)
C2—C31.401 (3)C13—H130.9300
C2—C71.403 (3)C15—C161.494 (3)
C3—C41.376 (4)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.386 (4)C16—H16C0.9600
C4—H40.9300C17—C181.494 (3)
C5—C61.379 (4)C18—H18A0.9600
C5—H50.9300C18—H18B0.9600
C6—C71.387 (3)C18—H18C0.9600
C15—O3—C11117.07 (19)C9—C10—C1119.7 (2)
C17—O5—C14118.35 (18)C12—C11—C10121.9 (2)
O1—C1—C2120.6 (2)C12—C11—O3116.2 (2)
O1—C1—C10121.2 (2)C10—C11—O3121.8 (2)
C2—C1—C10118.13 (19)C13—C12—C11119.5 (3)
C3—C2—C7119.3 (2)C13—C12—H12120.3
C3—C2—C1119.2 (2)C11—C12—H12120.3
C7—C2—C1121.5 (2)C14—C13—C12120.1 (2)
C4—C3—C2120.0 (2)C14—C13—H13119.9
C4—C3—H3120.0C12—C13—H13119.9
C2—C3—H3120.0C13—C14—O5116.3 (2)
C3—C4—C5120.4 (3)C13—C14—C9122.1 (2)
C3—C4—H4119.8O5—C14—C9121.3 (2)
C5—C4—H4119.8O4—C15—O3122.9 (2)
C6—C5—C4120.4 (3)O4—C15—C16126.7 (2)
C6—C5—H5119.8O3—C15—C16110.3 (2)
C4—C5—H5119.8C15—C16—H16A109.5
C5—C6—C7120.0 (2)C15—C16—H16B109.5
C5—C6—H6120.0H16A—C16—H16B109.5
C7—C6—H6120.0C15—C16—H16C109.5
C6—C7—C2119.9 (2)H16A—C16—H16C109.5
C6—C7—C8119.3 (2)H16B—C16—H16C109.5
C2—C7—C8120.7 (2)O6—C17—O5123.0 (2)
O2—C8—C9122.9 (2)O6—C17—C18127.4 (2)
O2—C8—C7119.4 (2)O5—C17—C18109.6 (2)
C9—C8—C7117.76 (19)C17—C18—H18A109.5
C14—C9—C10117.6 (2)C17—C18—H18B109.5
C14—C9—C8121.31 (19)H18A—C18—H18B109.5
C10—C9—C8121.1 (2)C17—C18—H18C109.5
C11—C10—C9118.8 (2)H18A—C18—H18C109.5
C11—C10—C1121.5 (2)H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O2i0.962.513.425 (4)159
Symmetry code: (i) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC18H12O6
Mr324.28
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.208 (7), 9.730 (8), 9.902 (8)
α, β, γ (°)73.257 (16), 79.986 (14), 80.770 (14)
V (Å3)740.7 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.20 × 0.15 × 0.12
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.978, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		4006, 2610, 1616
Rint0.023
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.152, 1.01
No. of reflections2610
No. of parameters219
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.25, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O2i0.962.513.425 (4)159
Symmetry code: (i) −x+3, −y+1, −z+1.
 

Acknowledgements

The authors gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (grant Nos. 21072119, 21102086), Shanxi Provincial Natural Science Foundation (grant No. 2012021009–4), Shanxi Province Foundation for Returnee (grant No. 2012–007), the Taiyuan Technology star special (grant No. 12024703) and CAS Key Laboratory of Analytical Chemistry for Living Biosystems Open Foundation (grant No. ACL201304).

References

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 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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ISSN: 2056-9890
Volume 69| Part 5| May 2013| Page o788
https://doi.org/10.1107/S1600536813010635
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