3,3′-Oxybi[isobenzofuran-1(3H)-one]

Li, W.; Yin, H.; Wen, L.; Li, K.; Fan, W.

doi:10.1107/S1600536809038914

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2577

doi:10.1107/S1600536809038914

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3,3′-Oxybi[isobenzofuran-1(3H)-one]

Wenkuan Li,^a Handong Yin,^a ^* Liyuan Wen,^a Kang Li ^a and Weidong Fan ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 18 September 2009; accepted 25 September 2009; online 30 September 2009)

The title compound, C₁₆H₁₀O₅, consists of two isobenzofuran-1(3H)-one moieties which are linked by a bridging O atom. The two halves of the molecule display approximate non-crystallographic mirror symmetry. The dihedral angle between the two isobenzofuran-1(3H)-one ring systems is 53.18 (6) Å. Two chiral carbon centres are observed in the compound, but their absolute configurations could not be determined. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link molecules into zigzag chains along c. Additional C—H⋯O interactions connect adjacent chains.

Related literature

For general background to isobenzofuran-1(3H)-ones, see: Landge et al. (2008 ); Mukhopadhyay & Kundu (2001 ); Paradkar et al. (1998 ).

Experimental

Crystal data

C₁₆H₁₀O₅
M_r = 282.24
Monoclinic, P n
a = 4.4449 (6) Å
b = 6.4937 (8) Å
c = 22.222 (2) Å
β = 91.334 (1)°
V = 641.25 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.44 × 0.29 × 0.11 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.988
3081 measured reflections
1139 independent reflections
972 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.078
S = 1.01
1139 reflections
190 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O5ⁱ	0.93	2.68	3.407 (4)	136
C1—H1⋯O3ⁱⁱ	0.98	2.61	3.337 (4)	131
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: 10.1107/S1600536809038914/sj2658sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038914/sj2658Isup2.hkl

checkCIF report

Comment top

Isobenzofuran-1(3H)-ones represent an important class of natural products that possess significant biological properties (Landge et al., 2008). A number of isobenzofuran derivatives have been reported in the literature (Paradkar et al., 1998; Mukhopadhyay & Kundu, 2001). Herein, the crystal structure of the title compound is presented.

The title compound (Fig. 1) is composed of two isobenzofuran-1(3H) -one moieties which are linked together by a bridging O1 atom. The two moieties display approximate mirror symmetry. The two isobenzofuran-1(3H)-one ring systems are not coplanar and are twisted from each other by a dihedral angle of 53.18 (6)Å. The title compound is a chiral compound with two chiral centers at C₁ and C₉ but the absolute configuration could not be determined. In the crystal structure, C6—H6···O5 hydrogen bonds link molecules into zig-zag chains along c. Additional C1—H1···O3 interactions connect adjacent chains (Fig. 2).

Related literature top

For general background to isobenzofuran-1(3H)-ones, see: Landge et al. (2008); Mukhopadhyay & Kundu (2001); Paradkar et al. (1998).

Experimental top

The product was obtained by a simple synthetic method: A mixture of triphenylantimony (3.00 mmol) and phthalic acid (3.00 mmol) in a stoppered flask was heated to 383 K. The mixture was shaken for 2.5 h. The product was crytallized from a solution of dichloromethane/petroleum ether (1:1), and to afford the title compound unexpectedly.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed approximately along the b axis. H atoms are omitted for clarity.

3,3'-Oxybi[isobenzofuran-1(3H)-one] top

Crystal data top

C₁₆H₁₀O₅	F(000) = 292
M_r = 282.24	D_x = 1.462 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 1280 reflections
a = 4.4449 (6) Å	θ = 2.8–23.0°
b = 6.4937 (8) Å	µ = 0.11 mm⁻¹
c = 22.222 (2) Å	T = 298 K
β = 91.334 (1)°	Block, colorless
V = 641.25 (13) Å³	0.44 × 0.29 × 0.11 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	1139 independent reflections
Radiation source: fine-focus sealed tube	972 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −3→5
T_min = 0.953, T_max = 0.988	k = −7→7
3081 measured reflections	l = −26→26

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0502P)² + 0.0032P] where P = (F_o² + 2F_c²)/3
1139 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₆H₁₀O₅	V = 641.25 (13) Å³
M_r = 282.24	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 4.4449 (6) Å	µ = 0.11 mm⁻¹
b = 6.4937 (8) Å	T = 298 K
c = 22.222 (2) Å	0.44 × 0.29 × 0.11 mm
β = 91.334 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1139 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	972 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.988	R_int = 0.025
3081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.01	Δρ_max = 0.13 e Å⁻³
1139 reflections	Δρ_min = −0.13 e Å⁻³
190 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.4119 (4)	0.1516 (3)	0.04946 (8)	0.0445 (5)
O2	0.7298 (5)	0.4086 (3)	0.01338 (9)	0.0511 (6)
O3	0.7306 (7)	0.7164 (3)	−0.03192 (13)	0.0742 (8)
O4	0.6010 (5)	0.2116 (3)	0.14674 (10)	0.0581 (6)
O5	0.4721 (8)	0.2569 (4)	0.24282 (12)	0.0859 (9)
C1	0.6000 (7)	0.2076 (5)	0.00288 (13)	0.0401 (7)
H1	0.7583	0.1044	−0.0022	0.048*
C2	0.6456 (7)	0.5423 (5)	−0.03175 (14)	0.0494 (8)
C3	0.4189 (7)	0.2325 (4)	−0.05400 (13)	0.0414 (7)
C4	0.4482 (7)	0.4308 (5)	−0.07433 (13)	0.0445 (7)
C5	0.3011 (8)	0.4956 (6)	−0.12687 (14)	0.0555 (9)
H5	0.3231	0.6295	−0.1409	0.067*
C6	0.1225 (9)	0.3563 (6)	−0.15739 (15)	0.0620 (10)
H6	0.0207	0.3965	−0.1925	0.074*
C7	0.0922 (9)	0.1584 (6)	−0.13675 (16)	0.0598 (9)
H7	−0.0305	0.0669	−0.1582	0.072*
C8	0.2407 (7)	0.0915 (5)	−0.08456 (14)	0.0499 (8)
H8	0.2207	−0.0430	−0.0708	0.060*
C9	0.5534 (7)	0.0616 (5)	0.10002 (14)	0.0443 (7)
H9	0.7448	−0.0014	0.0890	0.053*
C10	0.4522 (8)	0.1563 (5)	0.19777 (15)	0.0561 (9)
C11	0.3520 (6)	−0.0951 (4)	0.12751 (13)	0.0383 (7)
C12	0.2908 (6)	−0.0361 (5)	0.18517 (12)	0.0398 (7)
C13	0.1088 (8)	−0.1539 (6)	0.22104 (14)	0.0527 (8)
H13	0.0671	−0.1132	0.2601	0.063*
C14	−0.0088 (8)	−0.3326 (5)	0.19756 (16)	0.0567 (9)
H14	−0.1309	−0.4152	0.2209	0.068*
C15	0.0531 (8)	−0.3905 (5)	0.13930 (15)	0.0565 (9)
H15	−0.0294	−0.5119	0.1240	0.068*
C16	0.2336 (7)	−0.2733 (5)	0.10336 (14)	0.0475 (8)
H16	0.2740	−0.3131	0.0642	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0407 (11)	0.0523 (13)	0.0405 (11)	0.0026 (9)	0.0024 (9)	0.0118 (10)
O2	0.0571 (13)	0.0440 (13)	0.0520 (12)	−0.0096 (11)	−0.0019 (10)	0.0043 (11)
O3	0.097 (2)	0.0396 (14)	0.0862 (17)	−0.0174 (15)	0.0044 (15)	0.0040 (13)
O4	0.0705 (15)	0.0480 (13)	0.0551 (14)	−0.0231 (12)	−0.0137 (11)	0.0084 (11)
O5	0.132 (3)	0.0649 (18)	0.0596 (15)	−0.0248 (17)	−0.0195 (16)	−0.0118 (14)
C1	0.0425 (17)	0.0349 (15)	0.0430 (16)	−0.0007 (13)	0.0061 (13)	0.0023 (13)
C2	0.055 (2)	0.0401 (19)	0.0534 (18)	−0.0032 (15)	0.0119 (16)	0.0017 (16)
C3	0.0455 (17)	0.0412 (17)	0.0382 (15)	0.0043 (15)	0.0114 (13)	−0.0021 (14)
C4	0.0517 (18)	0.0407 (17)	0.0416 (16)	0.0028 (15)	0.0144 (14)	0.0031 (14)
C5	0.070 (2)	0.0505 (19)	0.0468 (18)	0.0112 (18)	0.0135 (17)	0.0141 (17)
C6	0.068 (2)	0.076 (3)	0.0421 (19)	0.012 (2)	0.0024 (17)	0.0031 (18)
C7	0.060 (2)	0.073 (3)	0.0467 (18)	−0.0015 (18)	0.0011 (16)	−0.0067 (19)
C8	0.056 (2)	0.0453 (19)	0.0483 (18)	−0.0011 (16)	0.0072 (15)	−0.0006 (15)
C9	0.0421 (16)	0.0425 (18)	0.0479 (17)	−0.0022 (14)	−0.0052 (13)	0.0075 (14)
C10	0.072 (2)	0.0447 (19)	0.051 (2)	−0.0063 (17)	−0.0157 (18)	0.0046 (17)
C11	0.0325 (14)	0.0384 (17)	0.0437 (16)	0.0012 (13)	−0.0046 (12)	0.0066 (13)
C12	0.0415 (15)	0.0410 (17)	0.0367 (15)	−0.0018 (14)	−0.0058 (12)	0.0053 (13)
C13	0.0552 (19)	0.064 (2)	0.0389 (16)	−0.0008 (18)	−0.0001 (14)	0.0066 (16)
C14	0.054 (2)	0.056 (2)	0.060 (2)	−0.0156 (17)	0.0015 (17)	0.0150 (17)
C15	0.062 (2)	0.0431 (18)	0.064 (2)	−0.0142 (17)	−0.0052 (17)	0.0016 (17)
C16	0.0485 (19)	0.0449 (18)	0.0490 (18)	−0.0032 (15)	−0.0011 (15)	−0.0036 (15)

Geometric parameters (Å, º) top

O1—C1	1.394 (3)	C6—H6	0.9300
O1—C9	1.403 (4)	C7—C8	1.391 (5)
O2—C2	1.372 (4)	C7—H7	0.9300
O2—C1	1.444 (4)	C8—H8	0.9300
O3—C2	1.192 (4)	C9—C11	1.495 (4)
O4—C10	1.374 (4)	C9—H9	0.9800
O4—C9	1.436 (4)	C10—C12	1.465 (5)
O5—C10	1.197 (4)	C11—C12	1.371 (4)
C1—C3	1.491 (4)	C11—C16	1.375 (4)
C1—H1	0.9800	C12—C13	1.380 (4)
C2—C4	1.467 (4)	C13—C14	1.371 (5)
C3—C4	1.372 (4)	C13—H13	0.9300
C3—C8	1.379 (4)	C14—C15	1.382 (5)
C4—C5	1.390 (4)	C14—H14	0.9300
C5—C6	1.373 (5)	C15—C16	1.375 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.372 (5)	C16—H16	0.9300

C1—O1—C9	116.0 (2)	C7—C8—H8	121.3
C2—O2—C1	110.6 (2)	O1—C9—O4	110.6 (2)
C10—O4—C9	110.7 (2)	O1—C9—C11	110.4 (2)
O1—C1—O2	111.1 (2)	O4—C9—C11	104.2 (2)
O1—C1—C3	109.6 (2)	O1—C9—H9	110.5
O2—C1—C3	104.2 (2)	O4—C9—H9	110.5
O1—C1—H1	110.6	C11—C9—H9	110.5
O2—C1—H1	110.6	O5—C10—O4	121.4 (3)
C3—C1—H1	110.6	O5—C10—C12	130.7 (3)
O3—C2—O2	121.4 (3)	O4—C10—C12	107.9 (3)
O3—C2—C4	130.6 (3)	C12—C11—C16	121.1 (3)
O2—C2—C4	108.0 (2)	C12—C11—C9	109.0 (3)
C4—C3—C8	121.3 (3)	C16—C11—C9	129.8 (3)
C4—C3—C1	109.1 (3)	C11—C12—C13	121.1 (3)
C8—C3—C1	129.6 (3)	C11—C12—C10	108.1 (3)
C3—C4—C5	120.9 (3)	C13—C12—C10	130.8 (3)
C3—C4—C2	108.1 (3)	C14—C13—C12	118.2 (3)
C5—C4—C2	130.9 (3)	C14—C13—H13	120.9
C6—C5—C4	118.1 (3)	C12—C13—H13	120.9
C6—C5—H5	121.0	C13—C14—C15	120.3 (3)
C4—C5—H5	121.0	C13—C14—H14	119.9
C7—C6—C5	120.8 (3)	C15—C14—H14	119.9
C7—C6—H6	119.6	C16—C15—C14	121.7 (3)
C5—C6—H6	119.6	C16—C15—H15	119.2
C6—C7—C8	121.5 (4)	C14—C15—H15	119.2
C6—C7—H7	119.2	C11—C16—C15	117.5 (3)
C8—C7—H7	119.2	C11—C16—H16	121.2
C3—C8—C7	117.3 (3)	C15—C16—H16	121.2
C3—C8—H8	121.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O5ⁱ	0.93	2.68	3.407 (4)	136
C1—H1···O3ⁱⁱ	0.98	2.61	3.337 (4)	131

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀O₅
M_r	282.24
Crystal system, space group	Monoclinic, Pn
Temperature (K)	298
a, b, c (Å)	4.4449 (6), 6.4937 (8), 22.222 (2)
β (°)	91.334 (1)
V (Å³)	641.25 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.44 × 0.29 × 0.11

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	3081, 1139, 972
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.01
No. of reflections	1139
No. of parameters	190
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
C6—H6···O5ⁱ	0.93	2.68	3.407 (4)	135.9
C1—H1···O3ⁱⁱ	0.98	2.61	3.337 (4)	131.3

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

Acknowledgements

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the `Students Technology Cultural Innovation Fund' of Liaocheng University.

References

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