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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2961.
Published online 2009 October 31. doi:  10.1107/S1600536809044961
PMCID: PMC2971025

(1R,1′S)-1,1′-Dihydr­oxy-1,1′-biisobenzofuran-3,3′(1H,1′H)-dione

Abstract

In the title compound, C16H10O6, the complete mol­ecule is generated by a crystallographic centre of symmetry. In the crystal, O—H(...)O hydrogen bonds link the mol­ecules into (100) sheets and C—H(...)O links also occur.

Related literature

For background to phthalides as natural products, see: Pedrosa et al. (2006 [triangle]). For a related structure, see: Wang et al. (2001 [triangle]).

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Object name is e-65-o2961-scheme1.jpg

Experimental

Crystal data

  • C16H10O6
  • M r = 298.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2961-efi1.jpg
  • a = 8.2260 (16) Å
  • b = 7.9690 (16) Å
  • c = 10.859 (4) Å
  • β = 114.03 (2)°
  • V = 650.1 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 293 K
  • 0.16 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 1352 measured reflections
  • 1263 independent reflections
  • 622 reflections with I > 2σ(I)
  • R int = 0.070

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.170
  • S = 1.02
  • 1263 reflections
  • 121 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044961/hb5170sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044961/hb5170Isup2.hkl

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

Acknowledgments

The authors would like to thank the National Natural Science Foundation of Shandong (Y2007B14, Y2008B29) and Weifang University for a research grant.

supplementary crystallographic information

Comment

Substituted phthalides (isobenzofuran-1(3H)-ones) represent an important class of natural products that posses significant biological properties (e.g. Pedrosa et al., 2006). As part of our search for new biologically active compounds, we unexpected obtained the title compound, (I), which is a typical derivative of phthalides.

In the crystal structure of compound (I) (Fig. 1),there is an inversion center, which is located at the mid-point of C(8)—C(8 A) bond. All of the bond lengths and bond angles are in the normal ranges (Wang et al., 2001). In the crystal lattice, there are a C—H···O intramolecular hydrogen bond and an O—H···O intermolecular hydrogen bond, which stabilize the molecule structure.

Experimental

Phthalic anhydride (0.05 mol) was dissolved in dichloromethane (100 ml). Then, AlCl3 (0.05 mol) was added. The mixture was stirred at room temperature and the whole reaction was under the protection of nitrogen. After 5 h, the reaction was stopped and the mixture poured into ice-water. The organic layer was collected and then was dried with MgSO4. Finally, the organic layer was concentrated by rotary vacuum evaporation to obtain yellow solids. Yellow blocks of (I) were obtailed by recrystallization from acetonitrile at room temperature.

Refinement

The H atoms were located in difference maps and freely refined.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C16H10O6F(000) = 308
Mr = 298.24Dx = 1.523 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1978 reflections
a = 8.2260 (16) Åθ = 3.5–27.5°
b = 7.9690 (16) ŵ = 0.12 mm1
c = 10.859 (4) ÅT = 293 K
β = 114.03 (2)°Block, yellow
V = 650.1 (3) Å30.16 × 0.12 × 0.10 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer622 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.070
graphiteθmax = 25.9°, θmin = 2.7°
ω scansh = 0→9
1352 measured reflectionsk = −9→0
1263 independent reflectionsl = −13→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170w = 1/[σ2(Fo2) + (0.0846P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1263 reflectionsΔρmax = 0.29 e Å3
121 parametersΔρmin = −0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (10)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.2464 (4)0.3665 (4)0.1300 (3)0.0549 (9)
O20.6822 (3)0.5869 (4)0.4778 (3)0.0410 (8)
O30.4600 (3)0.4127 (3)0.3342 (2)0.0376 (8)
C10.3733 (5)0.6782 (5)0.3741 (3)0.0314 (9)
C20.3529 (6)0.8340 (5)0.4222 (4)0.0398 (11)
C30.2204 (6)0.9369 (6)0.3366 (4)0.0467 (11)
C40.1095 (6)0.8864 (6)0.2078 (4)0.0484 (12)
C50.1271 (5)0.7290 (6)0.1605 (4)0.0408 (11)
C60.2612 (5)0.6276 (5)0.2465 (3)0.0316 (9)
C70.3138 (5)0.4584 (5)0.2258 (3)0.0359 (10)
C80.5080 (5)0.5441 (5)0.4390 (3)0.0330 (10)
H2A0.435 (5)0.868 (4)0.511 (4)0.036 (10)*
H4A0.014 (5)0.956 (6)0.148 (4)0.052 (12)*
H5A0.052 (5)0.686 (5)0.073 (3)0.036 (10)*
H3A0.206 (6)1.043 (7)0.368 (4)0.069 (15)*
H2B0.689 (9)0.669 (8)0.422 (6)0.12 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.067 (2)0.049 (2)0.0364 (15)0.0066 (16)0.0091 (15)−0.0153 (15)
O20.0378 (16)0.0411 (18)0.0391 (15)−0.0008 (14)0.0105 (13)0.0080 (13)
O30.0498 (17)0.0327 (16)0.0273 (13)0.0054 (13)0.0125 (13)−0.0038 (12)
C10.036 (2)0.028 (2)0.0265 (18)−0.0023 (16)0.0096 (17)0.0042 (16)
C20.052 (3)0.032 (2)0.0280 (19)−0.003 (2)0.008 (2)−0.0055 (18)
C30.057 (3)0.035 (3)0.046 (2)0.010 (2)0.018 (2)0.000 (2)
C40.045 (3)0.049 (3)0.043 (2)0.011 (2)0.009 (2)0.008 (2)
C50.039 (2)0.048 (3)0.028 (2)0.000 (2)0.0058 (18)−0.003 (2)
C60.035 (2)0.032 (2)0.0263 (18)0.0009 (17)0.0107 (17)0.0015 (16)
C70.044 (2)0.037 (3)0.0251 (19)−0.0039 (19)0.0119 (18)−0.0032 (17)
C80.037 (2)0.030 (2)0.0262 (18)0.0016 (18)0.0074 (17)−0.0005 (16)

Geometric parameters (Å, °)

O1—C71.207 (4)C2—H2A0.96 (4)
O2—C81.362 (4)C3—C41.382 (6)
O2—H2B0.91 (7)C3—H3A0.94 (5)
O3—C71.346 (4)C4—C51.385 (6)
O3—C81.477 (4)C4—H4A0.96 (4)
C1—C61.376 (5)C5—C61.380 (5)
C1—C21.383 (5)C5—H5A0.96 (4)
C1—C81.494 (5)C6—C71.461 (5)
C2—C31.378 (6)C8—C8i1.551 (7)
C8—O2—H2B108 (4)C6—C5—H5A118 (2)
C7—O3—C8110.2 (3)C4—C5—H5A125 (2)
C6—C1—C2120.6 (4)C1—C6—C5122.2 (4)
C6—C1—C8109.2 (3)C1—C6—C7107.9 (3)
C2—C1—C8130.2 (3)C5—C6—C7129.9 (3)
C3—C2—C1117.6 (4)O1—C7—O3121.5 (4)
C3—C2—H2A123 (2)O1—C7—C6129.2 (4)
C1—C2—H2A119 (2)O3—C7—C6109.3 (3)
C2—C3—C4121.6 (5)O2—C8—O3109.5 (3)
C2—C3—H3A118 (3)O2—C8—C1116.8 (3)
C4—C3—H3A120 (3)O3—C8—C1103.2 (3)
C3—C4—C5120.9 (4)O2—C8—C8i107.1 (4)
C3—C4—H4A122 (2)O3—C8—C8i104.4 (4)
C5—C4—H4A117 (2)C1—C8—C8i115.0 (4)
C6—C5—C4117.1 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2B···O1ii0.91 (7)1.82 (7)2.691 (5)159 (5)
C5—H5A···O1iii0.96 (3)2.58 (4)3.475 (5)155 (3)

Symmetry codes: (ii) −x+1, y+1/2, −z+1/2; (iii) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5170).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Pedrosa, R., Sayalero, S. & Vicente, M. (2006). Tetrahedron, 62, 10400–10404.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, X. Q., Song, M. Y. & Long, Y. C. (2001). J. Solid State Chem.156, 325–330.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography