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

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3,3′-Oxybi[isobenzo­furan-1(3H)-one]

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[Landge, S. M., Berryman, M. & Török, B. (2008). Tetrahedron Lett. 49, 4505-4508.]); Mukhopadhyay & Kundu (2001[Mukhopadhyay, R. & Kundu, N. G. (2001). Tetrahedron, 57, 9475-9480.]); Paradkar et al. (1998[Paradkar, M. V., Ranade, A. A., Kulkarni, M. S., Godbole, H. M. & Joseph, A. R. (1998). J. Chem. Res. (S), pp. 332-333.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10O5

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.953, Tmax = 0.988

  • 3081 measured reflections

  • 1139 independent reflections

  • 972 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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


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.

Refinement top

In the absence of significant anomalous scattering effects, 1139 Friedel pairs were merged. H atoms were positioned geometrically, and constrained to ride on their parent atoms, with C—H = 0.93 and 0.98 Å for aromatic and methine H atoms, respectively. and with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] 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
C16H10O5F(000) = 292
Mr = 282.24Dx = 1.462 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 1280 reflections
a = 4.4449 (6) Åθ = 2.8–23.0°
b = 6.4937 (8) ŵ = 0.11 mm1
c = 22.222 (2) ÅT = 298 K
β = 91.334 (1)°Block, colorless
V = 641.25 (13) Å30.44 × 0.29 × 0.11 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
1139 independent reflections
Radiation source: fine-focus sealed tube972 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 35
Tmin = 0.953, Tmax = 0.988k = 77
3081 measured reflectionsl = 2626
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.0032P]
where P = (Fo2 + 2Fc2)/3
1139 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.13 e Å3
2 restraintsΔρmin = 0.13 e Å3
Crystal data top
C16H10O5V = 641.25 (13) Å3
Mr = 282.24Z = 2
Monoclinic, PnMo Kα radiation
a = 4.4449 (6) ŵ = 0.11 mm1
b = 6.4937 (8) ÅT = 298 K
c = 22.222 (2) Å0.44 × 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)
Tmin = 0.953, Tmax = 0.988Rint = 0.025
3081 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0312 restraints
wR(F2) = 0.078H-atom parameters constrained
S = 1.01Δρmax = 0.13 e Å3
1139 reflectionsΔρmin = 0.13 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4119 (4)0.1516 (3)0.04946 (8)0.0445 (5)
O20.7298 (5)0.4086 (3)0.01338 (9)0.0511 (6)
O30.7306 (7)0.7164 (3)0.03192 (13)0.0742 (8)
O40.6010 (5)0.2116 (3)0.14674 (10)0.0581 (6)
O50.4721 (8)0.2569 (4)0.24282 (12)0.0859 (9)
C10.6000 (7)0.2076 (5)0.00288 (13)0.0401 (7)
H10.75830.10440.00220.048*
C20.6456 (7)0.5423 (5)0.03175 (14)0.0494 (8)
C30.4189 (7)0.2325 (4)0.05400 (13)0.0414 (7)
C40.4482 (7)0.4308 (5)0.07433 (13)0.0445 (7)
C50.3011 (8)0.4956 (6)0.12687 (14)0.0555 (9)
H50.32310.62950.14090.067*
C60.1225 (9)0.3563 (6)0.15739 (15)0.0620 (10)
H60.02070.39650.19250.074*
C70.0922 (9)0.1584 (6)0.13675 (16)0.0598 (9)
H70.03050.06690.15820.072*
C80.2407 (7)0.0915 (5)0.08456 (14)0.0499 (8)
H80.22070.04300.07080.060*
C90.5534 (7)0.0616 (5)0.10002 (14)0.0443 (7)
H90.74480.00140.08900.053*
C100.4522 (8)0.1563 (5)0.19777 (15)0.0561 (9)
C110.3520 (6)0.0951 (4)0.12751 (13)0.0383 (7)
C120.2908 (6)0.0361 (5)0.18517 (12)0.0398 (7)
C130.1088 (8)0.1539 (6)0.22104 (14)0.0527 (8)
H130.06710.11320.26010.063*
C140.0088 (8)0.3326 (5)0.19756 (16)0.0567 (9)
H140.13090.41520.22090.068*
C150.0531 (8)0.3905 (5)0.13930 (15)0.0565 (9)
H150.02940.51190.12400.068*
C160.2336 (7)0.2733 (5)0.10336 (14)0.0475 (8)
H160.27400.31310.06420.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0407 (11)0.0523 (13)0.0405 (11)0.0026 (9)0.0024 (9)0.0118 (10)
O20.0571 (13)0.0440 (13)0.0520 (12)0.0096 (11)0.0019 (10)0.0043 (11)
O30.097 (2)0.0396 (14)0.0862 (17)0.0174 (15)0.0044 (15)0.0040 (13)
O40.0705 (15)0.0480 (13)0.0551 (14)0.0231 (12)0.0137 (11)0.0084 (11)
O50.132 (3)0.0649 (18)0.0596 (15)0.0248 (17)0.0195 (16)0.0118 (14)
C10.0425 (17)0.0349 (15)0.0430 (16)0.0007 (13)0.0061 (13)0.0023 (13)
C20.055 (2)0.0401 (19)0.0534 (18)0.0032 (15)0.0119 (16)0.0017 (16)
C30.0455 (17)0.0412 (17)0.0382 (15)0.0043 (15)0.0114 (13)0.0021 (14)
C40.0517 (18)0.0407 (17)0.0416 (16)0.0028 (15)0.0144 (14)0.0031 (14)
C50.070 (2)0.0505 (19)0.0468 (18)0.0112 (18)0.0135 (17)0.0141 (17)
C60.068 (2)0.076 (3)0.0421 (19)0.012 (2)0.0024 (17)0.0031 (18)
C70.060 (2)0.073 (3)0.0467 (18)0.0015 (18)0.0011 (16)0.0067 (19)
C80.056 (2)0.0453 (19)0.0483 (18)0.0011 (16)0.0072 (15)0.0006 (15)
C90.0421 (16)0.0425 (18)0.0479 (17)0.0022 (14)0.0052 (13)0.0075 (14)
C100.072 (2)0.0447 (19)0.051 (2)0.0063 (17)0.0157 (18)0.0046 (17)
C110.0325 (14)0.0384 (17)0.0437 (16)0.0012 (13)0.0046 (12)0.0066 (13)
C120.0415 (15)0.0410 (17)0.0367 (15)0.0018 (14)0.0058 (12)0.0053 (13)
C130.0552 (19)0.064 (2)0.0389 (16)0.0008 (18)0.0001 (14)0.0066 (16)
C140.054 (2)0.056 (2)0.060 (2)0.0156 (17)0.0015 (17)0.0150 (17)
C150.062 (2)0.0431 (18)0.064 (2)0.0142 (17)0.0052 (17)0.0016 (17)
C160.0485 (19)0.0449 (18)0.0490 (18)0.0032 (15)0.0011 (15)0.0036 (15)
Geometric parameters (Å, º) top
O1—C11.394 (3)C6—H60.9300
O1—C91.403 (4)C7—C81.391 (5)
O2—C21.372 (4)C7—H70.9300
O2—C11.444 (4)C8—H80.9300
O3—C21.192 (4)C9—C111.495 (4)
O4—C101.374 (4)C9—H90.9800
O4—C91.436 (4)C10—C121.465 (5)
O5—C101.197 (4)C11—C121.371 (4)
C1—C31.491 (4)C11—C161.375 (4)
C1—H10.9800C12—C131.380 (4)
C2—C41.467 (4)C13—C141.371 (5)
C3—C41.372 (4)C13—H130.9300
C3—C81.379 (4)C14—C151.382 (5)
C4—C51.390 (4)C14—H140.9300
C5—C61.373 (5)C15—C161.375 (4)
C5—H50.9300C15—H150.9300
C6—C71.372 (5)C16—H160.9300
C1—O1—C9116.0 (2)C7—C8—H8121.3
C2—O2—C1110.6 (2)O1—C9—O4110.6 (2)
C10—O4—C9110.7 (2)O1—C9—C11110.4 (2)
O1—C1—O2111.1 (2)O4—C9—C11104.2 (2)
O1—C1—C3109.6 (2)O1—C9—H9110.5
O2—C1—C3104.2 (2)O4—C9—H9110.5
O1—C1—H1110.6C11—C9—H9110.5
O2—C1—H1110.6O5—C10—O4121.4 (3)
C3—C1—H1110.6O5—C10—C12130.7 (3)
O3—C2—O2121.4 (3)O4—C10—C12107.9 (3)
O3—C2—C4130.6 (3)C12—C11—C16121.1 (3)
O2—C2—C4108.0 (2)C12—C11—C9109.0 (3)
C4—C3—C8121.3 (3)C16—C11—C9129.8 (3)
C4—C3—C1109.1 (3)C11—C12—C13121.1 (3)
C8—C3—C1129.6 (3)C11—C12—C10108.1 (3)
C3—C4—C5120.9 (3)C13—C12—C10130.8 (3)
C3—C4—C2108.1 (3)C14—C13—C12118.2 (3)
C5—C4—C2130.9 (3)C14—C13—H13120.9
C6—C5—C4118.1 (3)C12—C13—H13120.9
C6—C5—H5121.0C13—C14—C15120.3 (3)
C4—C5—H5121.0C13—C14—H14119.9
C7—C6—C5120.8 (3)C15—C14—H14119.9
C7—C6—H6119.6C16—C15—C14121.7 (3)
C5—C6—H6119.6C16—C15—H15119.2
C6—C7—C8121.5 (4)C14—C15—H15119.2
C6—C7—H7119.2C11—C16—C15117.5 (3)
C8—C7—H7119.2C11—C16—H16121.2
C3—C8—C7117.3 (3)C15—C16—H16121.2
C3—C8—H8121.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O5i0.932.683.407 (4)136
C1—H1···O3ii0.982.613.337 (4)131
Symmetry codes: (i) x1/2, y+1, z1/2; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC16H10O5
Mr282.24
Crystal system, space groupMonoclinic, Pn
Temperature (K)298
a, b, c (Å)4.4449 (6), 6.4937 (8), 22.222 (2)
β (°) 91.334 (1)
V3)641.25 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.44 × 0.29 × 0.11
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.953, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
3081, 1139, 972
Rint0.025
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.078, 1.01
No. of reflections1139
No. of parameters190
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C6—H6···O5i0.932.683.407 (4)135.9
C1—H1···O3ii0.982.613.337 (4)131.3
Symmetry codes: (i) x1/2, y+1, z1/2; (ii) x, y1, 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

First citationLandge, S. M., Berryman, M. & Török, B. (2008). Tetrahedron Lett. 49, 4505–4508.  Web of Science CrossRef CAS Google Scholar
First citationMukhopadhyay, R. & Kundu, N. G. (2001). Tetrahedron, 57, 9475–9480.  Web of Science CrossRef CAS Google Scholar
First citationParadkar, M. V., Ranade, A. A., Kulkarni, M. S., Godbole, H. M. & Joseph, A. R. (1998). J. Chem. Res. (S), pp. 332–333.  Web of Science CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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