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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 68| Part 10| October 2012| Page o2843
https://doi.org/10.1107/S1600536812037361

2,6-Dimeth­­oxy-9,10-anthra­quinone

Akira Ohta,a Kazuki Hattori,a Takashi Kobayashi,b Hiroyoshi Naito,b Takeshi Kawasec and Chitoshi Kitamurac*

aDepartment of Chemistry, Faculty of Science, Shinshu University, 3-1-1 Asahi, Matsumoto, Nagano 390-8621, Japan, bDepartment of Physics and Electronics, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuencho, Naka-ku, Sakai, Osaka 599-8531, Japan, and cDepartment of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan
*Correspondence e-mail: kitamura@eng.u-hyogo.ac.jp

(Received 10 August 2012; accepted 30 August 2012; online 5 September 2012)

The title compound, C16H12O4, crystallizes with two half-mol­ecules in the asymmetric unit, each of which is completed by a crystallographic inversion center. The two crystallographically independent mol­ecules have almost the same geometry and are almost planar [maximum deviations = 0.018 (3) and 0.049 (3) Å]. They adopt a conformation in which the Cmeth­yl—O bonds are directed along the mol­ecular short axis [C—C—O—C torsion angles of 179.6 (2) and 178.0 (2)°]. In the crystal, the mol­ecular packing is characterized by a combination of a columnar stacking and a herringbone-like arrangement. The mol­ecules form slipped π-stacks along the b axis, in which there are two kinds of columns differing from each other in their slippage. The inter­planar distances between neighboring mol­ecules are 3.493 (3) for one column and 3.451 (2) Å for the other.

Related literature

For a study of the effects of alk­oxy substituents on the structures and solid-state photophysics of anthraquinones, see: Ohta, Hattori, Kusumoto, et al. (2012[Ohta, A., Hattori, K., Kusumoto, Y., Kawase, T., Kobayashi, T., Naito, H. & Kitamura, C. (2012). Chem. Lett. 41, 674-676.]). For the synthesis, see: Keller & Rüchardt (1998[Keller, F. & Rüchardt, C. (1998). J. Prakt. Chem. 340, 642-648.]). For a related structure, see: Ohta, Hattori, Kawase, et al. (2012[Ohta, A., Hattori, K., Kawase, T., Kobayashi, T., Naito, H. & Kitamura, C. (2012). Acta Cryst. E68, o2587.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12O4

  • Mr = 268.26

  • Monoclinic, P 21 /a

  • a = 16.2689 (19) Å

  • b = 3.9357 (4) Å

  • c = 19.9510 (19) Å

  • β = 109.499 (3)°

  • V = 1204.2 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 223 K

  • 0.58 × 0.08 × 0.06 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • 10392 measured reflections

  • 2743 independent reflections

  • 1501 reflections with I > 2σ(I)

  • Rint = 0.066
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.178

  • S = 1.00

  • 2743 reflections

  • 183 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.28 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1999[Rigaku (1999). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812037361/kj2210sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037361/kj2210Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037361/kj2210Isup3.cml

checkCIF report


Comment top

9,10-Anthraquinone is an important building block of many dyes and pigments. Recently, we have investigated the effects of alkoxy substituents on the optical properties of anthraquinones both in solution and in the solid state (Ohta, Hattori, Kusumoto, et al., 2012). We have revealed the cystal structure of 2,3,6,7-tetramethoxy-9,10- anthraquinone (Ohta, Hattori, Kawase, et al., 2012). In order to elucidate the substitution effects of the methoxy groups on the crystal packing, the X-ray analysis of the title compound was performed.

The molecular structure of the title compound is shown in Fig. 1. The title compound crystallizes with two halves of the molecule in the asymmetric unit of the unit cell. The complete molecules are located on crystallographic inversion centers. The molecules are almost planar with the maximum deviation of 0.018 (3) Å for C8 in one molecule and 0.049 (3) Å for C16 in another molecule. The molecules prefer the conformations in which the Cmethyl—O bonds are directed along the short molecular axis. Thus, the torsion angles of C3—C2—O2—C8 and C11—C10—O4—C16 are 179.6 (2) and 178.0 (2)°, respectively. Theses conformations are similar to the coressponding moiety in 2,3,6,7-tetramethoxy-9,10-anthraquinone (Ohta, Hattori, Kawase, et al., 2012). However, there is a large difference in crystal packing between the title compound and 2,3,6,7-tetramethoxy-9,10-anthraquinone. As shown in Fig. 2, the crystal structure is characterized by a columnar stacking and a herrinbone-like arrangement, although 2,3,6,7-tetramethoxy- 9,10-anthraquinone molecules took a slipped-parallel arrangement. Along the b axis, there are two columns in which molecules form slipped π-stacks. The interplanar distances between neighboring molecules are 3.493 (3) Å for one column and 3.451 (2) Å for another column. Furthermore, the translational shifts of neighboring molecules in the stacks are as follows: For molecule 1 (C1–C8, O1, and O2), the slip distance between neighboring molecules is 3.94 Å, and the anthraquinone rings in the column slipped relative to each other along the long molecular axis by 0.59 Å and along the short molecular axis by 1.72 Å. In contrast, for molecules 2 (C9–C16, O3, and O4), the slip distance between neighboring molecules is 3.94 Å, and the anthraquinone rings in the column slipped relative to each other along the long molecular axis by 1.89 Å and along the short molecular axis by 0.05 Å.

To examine the influence of crystal packing on the solid-state fluorescence, the fluorescence spectrum and the absolute quantum yield of the title compound were measured with a Hamamatsu Photonics PMA11 calibrated optical multichannel analyzer with a solid-state blue laser (λex = 377 nm) and a Labsphere IS IS-040-SF integrating sphere, respectively. The crystals showed negligible fluorescence (Φ < 0.001). The fluorescence quenching may result from the π-stacked structure.

Related literature top

For a study of the effects of alkoxy substituents on the structures and solid-state photophysics of anthraquinones, see: Ohta, Hattori, Kusumoto, et al. (2012). For the synthesis, see: Keller & Rüchardt (1998). For a related structure, see: Ohta, Hattori, Kawase, et al. (2012).

Experimental top

The title compound was prepared according to the literature procedure (Keller & Rüchardt, 1998). Single crystals suitable for X-ray analysis were obtained by recrystallization from toluene.

Refinement top

All the H atoms were positioned geometrically and refined using a riding model with C—H = 0.94 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, and C—H = 0.97 Å and Uiso(H) = 1.5Ueq(C) for CH3. The positions of methyl H atoms were optimized rotationally.

Structure description top

9,10-Anthraquinone is an important building block of many dyes and pigments. Recently, we have investigated the effects of alkoxy substituents on the optical properties of anthraquinones both in solution and in the solid state (Ohta, Hattori, Kusumoto, et al., 2012). We have revealed the cystal structure of 2,3,6,7-tetramethoxy-9,10- anthraquinone (Ohta, Hattori, Kawase, et al., 2012). In order to elucidate the substitution effects of the methoxy groups on the crystal packing, the X-ray analysis of the title compound was performed.

The molecular structure of the title compound is shown in Fig. 1. The title compound crystallizes with two halves of the molecule in the asymmetric unit of the unit cell. The complete molecules are located on crystallographic inversion centers. The molecules are almost planar with the maximum deviation of 0.018 (3) Å for C8 in one molecule and 0.049 (3) Å for C16 in another molecule. The molecules prefer the conformations in which the Cmethyl—O bonds are directed along the short molecular axis. Thus, the torsion angles of C3—C2—O2—C8 and C11—C10—O4—C16 are 179.6 (2) and 178.0 (2)°, respectively. Theses conformations are similar to the coressponding moiety in 2,3,6,7-tetramethoxy-9,10-anthraquinone (Ohta, Hattori, Kawase, et al., 2012). However, there is a large difference in crystal packing between the title compound and 2,3,6,7-tetramethoxy-9,10-anthraquinone. As shown in Fig. 2, the crystal structure is characterized by a columnar stacking and a herrinbone-like arrangement, although 2,3,6,7-tetramethoxy- 9,10-anthraquinone molecules took a slipped-parallel arrangement. Along the b axis, there are two columns in which molecules form slipped π-stacks. The interplanar distances between neighboring molecules are 3.493 (3) Å for one column and 3.451 (2) Å for another column. Furthermore, the translational shifts of neighboring molecules in the stacks are as follows: For molecule 1 (C1–C8, O1, and O2), the slip distance between neighboring molecules is 3.94 Å, and the anthraquinone rings in the column slipped relative to each other along the long molecular axis by 0.59 Å and along the short molecular axis by 1.72 Å. In contrast, for molecules 2 (C9–C16, O3, and O4), the slip distance between neighboring molecules is 3.94 Å, and the anthraquinone rings in the column slipped relative to each other along the long molecular axis by 1.89 Å and along the short molecular axis by 0.05 Å.

To examine the influence of crystal packing on the solid-state fluorescence, the fluorescence spectrum and the absolute quantum yield of the title compound were measured with a Hamamatsu Photonics PMA11 calibrated optical multichannel analyzer with a solid-state blue laser (λex = 377 nm) and a Labsphere IS IS-040-SF integrating sphere, respectively. The crystals showed negligible fluorescence (Φ < 0.001). The fluorescence quenching may result from the π-stacked structure.

For a study of the effects of alkoxy substituents on the structures and solid-state photophysics of anthraquinones, see: Ohta, Hattori, Kusumoto, et al. (2012). For the synthesis, see: Keller & Rüchardt (1998). For a related structure, see: Ohta, Hattori, Kawase, et al. (2012).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 50% probability displacement ellipsoids. Symmetry code: (i) -x, -y + 1, -z. (ii) -x + 1, -y + 1, -z + 1.
[Figure 2] Fig. 2. The packing diagram of the title compound, viewed down the b axis. Hydrogen atoms are omitted for clarity.
2,6-dimethoxyanthracene-9,10-dione top
Crystal data top
C16H12O4F(000) = 560
Mr = 268.26Dx = 1.48 Mg m−3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 5015 reflections
a = 16.2689 (19) Åθ = 3.2–27.5°
b = 3.9357 (4) ŵ = 0.11 mm−1
c = 19.9510 (19) ÅT = 223 K
β = 109.499 (3)°Prism, yellow
V = 1204.2 (2) Å30.58 × 0.08 × 0.06 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		1501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed x-ray tubeRint = 0.066
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
Detector resolution: 10 pixels mm-1h = −21→21
ω scansk = −4→5
10392 measured reflectionsl = −22→25
2743 independent reflections
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0915P)2]
where P = (Fo2 + 2Fc2)/3
2743 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C16H12O4V = 1204.2 (2) Å3
Mr = 268.26Z = 4
Monoclinic, P21/aMo Kα radiation
a = 16.2689 (19) ŵ = 0.11 mm−1
b = 3.9357 (4) ÅT = 223 K
c = 19.9510 (19) Å0.58 × 0.08 × 0.06 mm
β = 109.499 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		1501 reflections with I > 2σ(I)
10392 measured reflectionsRint = 0.066
2743 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.00Δρmax = 0.26 e Å−3
2743 reflectionsΔρmin = −0.28 e Å−3
183 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C10.10535 (16)0.2528 (6)0.13534 (12)0.0412 (6)
H10.07850.14970.16520.049*
C20.19519 (17)0.2826 (6)0.15742 (12)0.0424 (6)
C30.23494 (17)0.4388 (6)0.11278 (12)0.0452 (6)
H30.2960.45820.12750.054*
C40.18464 (17)0.5631 (6)0.04772 (12)0.0444 (6)
H40.21170.66960.01840.053*
C50.09401 (16)0.5337 (6)0.02449 (11)0.0387 (6)
C60.05487 (16)0.3753 (6)0.06904 (11)0.0389 (6)
C7−0.04125 (16)0.3291 (6)0.04555 (11)0.0416 (6)
C80.21230 (19)0.0119 (7)0.26849 (13)0.0522 (7)
H8A0.179−0.18540.24550.078*
H8B0.17410.17180.28050.078*
H8C0.2581−0.05830.31150.078*
O1−0.07545 (12)0.1767 (5)0.08334 (8)0.0541 (5)
O20.25054 (12)0.1718 (5)0.22088 (8)0.0506 (5)
C90.47309 (16)0.1926 (6)0.36503 (12)0.0401 (6)
H90.41680.18980.3310.048*
C100.54271 (17)0.0488 (6)0.34963 (12)0.0424 (6)
C110.62617 (17)0.0536 (6)0.39982 (12)0.0444 (6)
H110.6731−0.04220.38880.053*
C120.64007 (17)0.1983 (6)0.46545 (12)0.0430 (6)
H120.69650.19820.49930.052*
C130.57121 (15)0.3458 (6)0.48250 (11)0.0380 (6)
C140.48757 (15)0.3411 (6)0.43153 (11)0.0377 (5)
C150.41234 (15)0.4966 (6)0.44723 (12)0.0409 (6)
C160.45117 (19)−0.1244 (8)0.23357 (13)0.0556 (7)
H16A0.4122−0.24540.25290.083*
H16B0.4552−0.24530.19240.083*
H16C0.42870.10260.21960.083*
O30.33925 (12)0.4938 (5)0.40245 (8)0.0542 (5)
O40.53622 (12)−0.1021 (5)0.28663 (8)0.0520 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0444 (15)0.0426 (13)0.0369 (11)−0.0015 (11)0.0141 (10)−0.0030 (10)
C20.0446 (15)0.0446 (13)0.0363 (11)0.0018 (11)0.0110 (10)−0.0005 (10)
C30.0375 (14)0.0536 (15)0.0446 (13)0.0014 (11)0.0137 (11)0.0008 (12)
C40.0445 (15)0.0486 (14)0.0421 (13)−0.0036 (11)0.0172 (11)−0.0037 (11)
C50.0400 (14)0.0402 (12)0.0369 (11)−0.0008 (10)0.0144 (10)−0.0015 (10)
C60.0425 (14)0.0399 (12)0.0361 (11)−0.0016 (10)0.0154 (10)−0.0019 (10)
C70.0439 (15)0.0441 (14)0.0374 (12)−0.0019 (11)0.0145 (11)−0.0030 (11)
C80.0523 (17)0.0594 (16)0.0422 (13)0.0005 (13)0.0122 (12)0.0069 (12)
O10.0466 (11)0.0721 (12)0.0454 (9)−0.0061 (9)0.0177 (8)0.0096 (9)
O20.0437 (11)0.0645 (12)0.0410 (9)0.0022 (8)0.0106 (8)0.0088 (8)
C90.0391 (14)0.0429 (13)0.0351 (11)0.0013 (10)0.0081 (9)0.0056 (10)
C100.0459 (15)0.0433 (13)0.0386 (12)0.0012 (11)0.0149 (11)0.0013 (11)
C110.0416 (15)0.0480 (14)0.0446 (13)0.0034 (11)0.0158 (11)0.0052 (11)
C120.0367 (14)0.0455 (13)0.0448 (13)0.0014 (10)0.0109 (10)0.0042 (11)
C130.0346 (13)0.0396 (12)0.0388 (12)0.0009 (10)0.0110 (10)0.0053 (10)
C140.0354 (13)0.0376 (12)0.0389 (11)0.0014 (10)0.0108 (10)0.0075 (10)
C150.0354 (14)0.0425 (13)0.0405 (12)0.0011 (10)0.0068 (10)0.0066 (11)
C160.0592 (19)0.0597 (17)0.0421 (13)0.0018 (13)0.0094 (12)−0.0066 (13)
O30.0367 (11)0.0701 (12)0.0484 (10)0.0058 (9)0.0042 (8)−0.0043 (9)
O40.0524 (12)0.0620 (11)0.0413 (9)0.0031 (9)0.0153 (8)−0.0049 (8)
Geometric parameters (Å, º) top
C1—C21.384 (4)C9—C101.389 (3)
C1—C61.390 (3)C9—C141.396 (3)
C1—H10.94C9—H90.94
C2—O21.357 (3)C10—O41.362 (3)
C2—C31.405 (3)C10—C111.392 (3)
C3—C41.373 (3)C11—C121.376 (3)
C3—H30.94C11—H110.94
C4—C51.395 (4)C12—C131.401 (3)
C4—H40.94C12—H120.94
C5—C61.401 (3)C13—C141.401 (3)
C5—C7i1.477 (3)C13—C15ii1.474 (3)
C6—C71.486 (3)C14—C151.492 (3)
C7—O11.232 (3)C15—O31.226 (3)
C7—C5i1.477 (3)C15—C13ii1.474 (3)
C8—O21.442 (3)C16—O41.437 (3)
C8—H8A0.97C16—H16A0.97
C8—H8B0.97C16—H16B0.97
C8—H8C0.97C16—H16C0.97
C2—C1—C6120.0 (2)C10—C9—C14119.3 (2)
C2—C1—H1120C10—C9—H9120.3
C6—C1—H1120C14—C9—H9120.3
O2—C2—C1124.8 (2)O4—C10—C9124.3 (2)
O2—C2—C3115.4 (2)O4—C10—C11115.2 (2)
C1—C2—C3119.7 (2)C9—C10—C11120.4 (2)
C4—C3—C2120.0 (2)C12—C11—C10120.1 (2)
C4—C3—H3120C12—C11—H11120
C2—C3—H3120C10—C11—H11120
C3—C4—C5121.0 (2)C11—C12—C13120.8 (2)
C3—C4—H4119.5C11—C12—H12119.6
C5—C4—H4119.5C13—C12—H12119.6
C4—C5—C6118.7 (2)C12—C13—C14118.7 (2)
C4—C5—C7i120.0 (2)C12—C13—C15ii120.0 (2)
C6—C5—C7i121.3 (2)C14—C13—C15ii121.3 (2)
C1—C6—C5120.6 (2)C9—C14—C13120.7 (2)
C1—C6—C7118.9 (2)C9—C14—C15118.8 (2)
C5—C6—C7120.5 (2)C13—C14—C15120.6 (2)
O1—C7—C5i121.2 (2)O3—C15—C13ii121.4 (2)
O1—C7—C6120.6 (2)O3—C15—C14120.5 (2)
C5i—C7—C6118.2 (2)C13ii—C15—C14118.1 (2)
O2—C8—H8A109.5O4—C16—H16A109.5
O2—C8—H8B109.5O4—C16—H16B109.5
H8A—C8—H8B109.5H16A—C16—H16B109.5
O2—C8—H8C109.5O4—C16—H16C109.5
H8A—C8—H8C109.5H16A—C16—H16C109.5
H8B—C8—H8C109.5H16B—C16—H16C109.5
C2—O2—C8117.2 (2)C10—O4—C16117.7 (2)
C6—C1—C2—O2−179.9 (2)C14—C9—C10—O4−179.9 (2)
C6—C1—C2—C30.4 (4)C14—C9—C10—C11−0.2 (4)
O2—C2—C3—C4−179.3 (2)O4—C10—C11—C12−179.7 (2)
C1—C2—C3—C40.4 (4)C9—C10—C11—C120.6 (4)
C2—C3—C4—C5−0.7 (4)C10—C11—C12—C13−0.7 (4)
C3—C4—C5—C60.2 (3)C11—C12—C13—C140.4 (4)
C3—C4—C5—C7i179.7 (2)C11—C12—C13—C15ii−179.2 (2)
C2—C1—C6—C5−0.9 (4)C10—C9—C14—C13−0.1 (3)
C2—C1—C6—C7177.9 (2)C10—C9—C14—C15179.6 (2)
C4—C5—C6—C10.6 (3)C12—C13—C14—C90.0 (3)
C7i—C5—C6—C1−178.9 (2)C15ii—C13—C14—C9179.6 (2)
C4—C5—C6—C7−178.1 (2)C12—C13—C14—C15−179.7 (2)
C7i—C5—C6—C72.4 (4)C15ii—C13—C14—C15−0.1 (4)
C1—C6—C7—O1−1.9 (3)C9—C14—C15—O3−0.1 (3)
C5—C6—C7—O1176.8 (2)C13—C14—C15—O3179.6 (2)
C1—C6—C7—C5i178.9 (2)C9—C14—C15—C13ii−179.6 (2)
C5—C6—C7—C5i−2.3 (4)C13—C14—C15—C13ii0.1 (4)
C1—C2—O2—C8−0.1 (3)C9—C10—O4—C16−2.3 (3)
C3—C2—O2—C8179.6 (2)C11—C10—O4—C16178.0 (2)
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC16H12O4
Mr268.26
Crystal system, space groupMonoclinic, P21/a
Temperature (K)223
a, b, c (Å)16.2689 (19), 3.9357 (4), 19.9510 (19)
β (°) 109.499 (3)
V (Å3)1204.2 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.58 × 0.08 × 0.06
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		10392, 2743, 1501
Rint0.066
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.178, 1.00
No. of reflections2743
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.26, −0.28

Computer programs: RAPID-AUTO (Rigaku, 1999), PROCESS-AUTO (Rigaku, 1998), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

This work was partly supported by Grant-in-Aid for Scientific Research (C) (No. 23550161) from JSPS and Grant-in-Aid for Scientific Research on Innovative Areas (No. 23108720, "pi-Space") from MEXT.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationKeller, F. & Rüchardt, C. (1998). J. Prakt. Chem. 340, 642–648.  Web of Science CrossRef CAS Google Scholar
 First citationOhta, A., Hattori, K., Kawase, T., Kobayashi, T., Naito, H. & Kitamura, C. (2012). Acta Cryst. E68, o2587.  CSD CrossRef IUCr Journals Google Scholar
 First citationOhta, A., Hattori, K., Kusumoto, Y., Kawase, T., Kobayashi, T., Naito, H. & Kitamura, C. (2012). Chem. Lett. 41, 674–676.  Web of Science CSD CrossRef CAS Google Scholar
 First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (1999). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2843
https://doi.org/10.1107/S1600536812037361
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