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

Jian, F.-F.; Zhao, S.-S.; Guo, H.-M.; Li, Y.-F.; Zhao, P.-S.

doi:10.1107/S1600536809044961

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2961

https://doi.org/10.1107/S1600536809044961

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

Fang-Fang Jian,^a ^* Shan-Shan Zhao,^b Huan-Mei Guo,^a Yu-Feng Li ^a and Pu-Su Zhao ^b

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bNew Materials and Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 22 October 2009; accepted 28 October 2009; online 31 October 2009)

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 ). For a related structure, see: Wang et al. (2001 ).

Experimental

Crystal data

C₁₆H₁₀O₆
M_r = 298.24
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.170
S = 1.02
1263 reflections
121 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O1ⁱ	0.91 (7)	1.82 (7)	2.691 (5)	159 (5)
C5—H5A⋯O1ⁱⁱ	0.96 (3)	2.58 (4)	3.475 (5)	155 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044961/hb5170Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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

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

(1R,1'S)-1,1'-dihydroxy-1,1'-biisobenzofuran- 3,3'(1H,1'H)-dione top

Crystal data top

C₁₆H₁₀O₆	F(000) = 308
M_r = 298.24	D_x = 1.523 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1978 reflections
a = 8.2260 (16) Å	θ = 3.5–27.5°
b = 7.9690 (16) Å	µ = 0.12 mm⁻¹
c = 10.859 (4) Å	T = 293 K
β = 114.03 (2)°	Block, yellow
V = 650.1 (3) Å³	0.16 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	622 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.070
Graphite monochromator	θ_max = 25.9°, θ_min = 2.7°
ω scans	h = 0→9
1352 measured reflections	k = −9→0
1263 independent reflections	l = −13→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.0846P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1263 reflections	Δρ_max = 0.29 e Å⁻³
121 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (10)

Crystal data top

C₁₆H₁₀O₆	V = 650.1 (3) Å³
M_r = 298.24	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2260 (16) Å	µ = 0.12 mm⁻¹
b = 7.9690 (16) Å	T = 293 K
c = 10.859 (4) Å	0.16 × 0.12 × 0.10 mm
β = 114.03 (2)°

Data collection top

Bruker SMART CCD diffractometer	622 reflections with I > 2σ(I)
1352 measured reflections	R_int = 0.070
1263 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.29 e Å⁻³
1263 reflections	Δρ_min = −0.30 e Å⁻³
121 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 > 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

	x	y	z	U_iso*/U_eq
O1	0.2464 (4)	0.3665 (4)	0.1300 (3)	0.0549 (9)
O2	0.6822 (3)	0.5869 (4)	0.4778 (3)	0.0410 (8)
O3	0.4600 (3)	0.4127 (3)	0.3342 (2)	0.0376 (8)
C1	0.3733 (5)	0.6782 (5)	0.3741 (3)	0.0314 (9)
C2	0.3529 (6)	0.8340 (5)	0.4222 (4)	0.0398 (11)
C3	0.2204 (6)	0.9369 (6)	0.3366 (4)	0.0467 (11)
C4	0.1095 (6)	0.8864 (6)	0.2078 (4)	0.0484 (12)
C5	0.1271 (5)	0.7290 (6)	0.1605 (4)	0.0408 (11)
C6	0.2612 (5)	0.6276 (5)	0.2465 (3)	0.0316 (9)
C7	0.3138 (5)	0.4584 (5)	0.2258 (3)	0.0359 (10)
C8	0.5080 (5)	0.5441 (5)	0.4390 (3)	0.0330 (10)
H2A	0.435 (5)	0.868 (4)	0.511 (4)	0.036 (10)*
H4A	0.014 (5)	0.956 (6)	0.148 (4)	0.052 (12)*
H5A	0.052 (5)	0.686 (5)	0.073 (3)	0.036 (10)*
H3A	0.206 (6)	1.043 (7)	0.368 (4)	0.069 (15)*
H2B	0.689 (9)	0.669 (8)	0.422 (6)	0.12 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.067 (2)	0.049 (2)	0.0364 (15)	0.0066 (16)	0.0091 (15)	−0.0153 (15)
O2	0.0378 (16)	0.0411 (18)	0.0391 (15)	−0.0008 (14)	0.0105 (13)	0.0080 (13)
O3	0.0498 (17)	0.0327 (16)	0.0273 (13)	0.0054 (13)	0.0125 (13)	−0.0038 (12)
C1	0.036 (2)	0.028 (2)	0.0265 (18)	−0.0023 (16)	0.0096 (17)	0.0042 (16)
C2	0.052 (3)	0.032 (2)	0.0280 (19)	−0.003 (2)	0.008 (2)	−0.0055 (18)
C3	0.057 (3)	0.035 (3)	0.046 (2)	0.010 (2)	0.018 (2)	0.000 (2)
C4	0.045 (3)	0.049 (3)	0.043 (2)	0.011 (2)	0.009 (2)	0.008 (2)
C5	0.039 (2)	0.048 (3)	0.028 (2)	0.000 (2)	0.0058 (18)	−0.003 (2)
C6	0.035 (2)	0.032 (2)	0.0263 (18)	0.0009 (17)	0.0107 (17)	0.0015 (16)
C7	0.044 (2)	0.037 (3)	0.0251 (19)	−0.0039 (19)	0.0119 (18)	−0.0032 (17)
C8	0.037 (2)	0.030 (2)	0.0262 (18)	0.0016 (18)	0.0074 (17)	−0.0005 (16)

Geometric parameters (Å, º) top

O1—C7	1.207 (4)	C2—H2A	0.96 (4)
O2—C8	1.362 (4)	C3—C4	1.382 (6)
O2—H2B	0.91 (7)	C3—H3A	0.94 (5)
O3—C7	1.346 (4)	C4—C5	1.385 (6)
O3—C8	1.477 (4)	C4—H4A	0.96 (4)
C1—C6	1.376 (5)	C5—C6	1.380 (5)
C1—C2	1.383 (5)	C5—H5A	0.96 (4)
C1—C8	1.494 (5)	C6—C7	1.461 (5)
C2—C3	1.378 (6)	C8—C8ⁱ	1.551 (7)

C8—O2—H2B	108 (4)	C6—C5—H5A	118 (2)
C7—O3—C8	110.2 (3)	C4—C5—H5A	125 (2)
C6—C1—C2	120.6 (4)	C1—C6—C5	122.2 (4)
C6—C1—C8	109.2 (3)	C1—C6—C7	107.9 (3)
C2—C1—C8	130.2 (3)	C5—C6—C7	129.9 (3)
C3—C2—C1	117.6 (4)	O1—C7—O3	121.5 (4)
C3—C2—H2A	123 (2)	O1—C7—C6	129.2 (4)
C1—C2—H2A	119 (2)	O3—C7—C6	109.3 (3)
C2—C3—C4	121.6 (5)	O2—C8—O3	109.5 (3)
C2—C3—H3A	118 (3)	O2—C8—C1	116.8 (3)
C4—C3—H3A	120 (3)	O3—C8—C1	103.2 (3)
C3—C4—C5	120.9 (4)	O2—C8—C8ⁱ	107.1 (4)
C3—C4—H4A	122 (2)	O3—C8—C8ⁱ	104.4 (4)
C5—C4—H4A	117 (2)	C1—C8—C8ⁱ	115.0 (4)
C6—C5—C4	117.1 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O1ⁱⁱ	0.91 (7)	1.82 (7)	2.691 (5)	159 (5)
C5—H5A···O1ⁱⁱⁱ	0.96 (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.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀O₆
M_r	298.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.2260 (16), 7.9690 (16), 10.859 (4)
β (°)	114.03 (2)
V (Å³)	650.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1352, 1263, 622
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.170, 1.02
No. of reflections	1263
No. of parameters	121
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O1ⁱ	0.91 (7)	1.82 (7)	2.691 (5)	159 (5)
C5—H5A···O1ⁱⁱ	0.96 (3)	2.58 (4)	3.475 (5)	155 (3)

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

Acknowledgements

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

References

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