PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1021.
Published online 2008 May 10. doi:  10.1107/S1600536808012452
PMCID: PMC2961621

Bicyclo­[2.2.2]oct-7-ene-2,3,5,6-tetra­carboxylic dianhydride

Abstract

In the title compound, C12H8O6, mol­ecules are linked by weak C—H(...)O inter­actions involving all the potential donors, generating a three-dimensional network.

An external file that holds a picture, illustration, etc.
Object name is e-64-o1021-scheme1.jpg

Experimental

Crystal data

  • C12H8O6
  • M r = 248.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1021-efi1.jpg
  • a = 7.627 (2) Å
  • b = 13.877 (3) Å
  • c = 9.823 (2) Å
  • β = 100.68 (2)°
  • V = 1021.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 296 (2) K
  • 0.28 × 0.16 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.921, T max = 0.987
  • 11412 measured reflections
  • 2119 independent reflections
  • 1460 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.099
  • S = 1.01
  • 2118 reflections
  • 164 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536808012452/sg2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012452/sg2233Isup2.hkl

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

Acknowledgments

The author acknowledges funding support from the Natural Science Foundation of Shanxi Province (2007011033), the Program of Technological Industrialization in Universities of Shanxi Province (20070308) and the Start-up Fund of the North University of China.

supplementary crystallographic information

Comment

The molecule of the title complex, (I) (Fig. 1), is neutral. Molecules are linked by C—H···O weak interactions involving all the potential donors, generating a three-dimensional network, as shown in Fig. 2. No conventional hydrogen bonding was found in the structure.

Experimental

The title compound was obtained unintentionally as the product of an attempted synthesis of a polymeric network complex of znic with the bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid. The title compound (0.4 mmol) and Zn(NO3)2. 6H2O (0.2 mmol) were dissolved in 15 ml distilled water, to which 2 drops of H3PO4 (w.t. 18%) was added. The solution was put into the oven at 50 centigrade degree for 1 day. Colourless prism crystals were collected by filtration.

Refinement

H atoms were positioned geometrically and refined using a riding model with C—H = 0.980 Å and 0.930 Å, respectively, with Uiso(H) = 1.2 times Ueq(C). Reflection -111 was omitted because it was eclipsed by the beam stop.

Figures

Fig. 1.
Molecular structure showing 50% probability displacement ellipsoids.
Fig. 2.
Packing diagram viewed down the a axis.

Crystal data

C12H8O6F000 = 512
Mr = 248.18Dx = 1.613 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2677 reflections
a = 7.627 (2) Åθ = 2.9–24.1º
b = 13.877 (3) ŵ = 0.13 mm1
c = 9.823 (2) ÅT = 296 (2) K
β = 100.68 (2)ºPrism, colourless
V = 1021.7 (4) Å30.28 × 0.16 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2119 independent reflections
Radiation source: fine-focus sealed tube1460 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
T = 296(2) Kθmax = 26.5º
[var phi] and ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.921, Tmax = 0.987k = −17→15
11412 measured reflectionsl = −11→12

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042  w = 1/[σ2(Fo2) + (0.0334P)2 + 0.3914P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.21 e Å3
2118 reflectionsΔρmin = −0.16 e Å3
164 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.005 (1)
Secondary atom site location: difference Fourier map

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
C10.7820 (3)0.83700 (16)0.6304 (2)0.0449 (5)
C20.5829 (2)0.84372 (13)0.61717 (19)0.0355 (4)
H20.52390.83810.52000.043*
C30.5305 (2)0.93909 (13)0.68048 (19)0.0350 (4)
H30.56460.99520.63070.042*
C40.3256 (2)0.93415 (13)0.67248 (18)0.0344 (4)
H40.26330.93010.57600.041*
C50.2627 (3)1.01999 (15)0.7435 (2)0.0416 (5)
C60.1858 (3)0.89126 (15)0.8635 (2)0.0434 (5)
C70.2788 (2)0.84782 (13)0.75613 (18)0.0352 (4)
H70.19840.80390.69620.042*
C80.4506 (2)0.79445 (13)0.82409 (18)0.0354 (4)
H80.42510.74130.88310.042*
C90.5347 (2)0.75817 (13)0.70190 (19)0.0358 (4)
H90.45260.71450.64290.043*
C100.7097 (3)0.70890 (16)0.7535 (2)0.0462 (5)
C110.5767 (2)0.86683 (14)0.90425 (19)0.0392 (5)
H110.62210.86020.99840.047*
C120.6180 (2)0.94061 (14)0.83043 (19)0.0394 (5)
H120.69510.98950.86860.047*
O10.88296 (19)0.89053 (13)0.58906 (17)0.0638 (5)
O20.7409 (2)0.64134 (12)0.82843 (18)0.0681 (5)
O30.2829 (2)1.10382 (11)0.72476 (16)0.0596 (4)
O40.1289 (2)0.85316 (12)0.95463 (16)0.0629 (5)
O50.84589 (17)0.75576 (11)0.70513 (15)0.0537 (4)
O60.17498 (18)0.99043 (10)0.84767 (14)0.0485 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0359 (11)0.0528 (13)0.0462 (12)0.0033 (10)0.0079 (9)−0.0067 (10)
C20.0311 (9)0.0378 (11)0.0373 (10)0.0016 (8)0.0054 (7)−0.0023 (8)
C30.0334 (9)0.0298 (10)0.0422 (10)−0.0030 (8)0.0076 (8)0.0016 (8)
C40.0337 (9)0.0331 (10)0.0351 (9)0.0039 (8)0.0031 (7)−0.0014 (8)
C50.0405 (11)0.0389 (12)0.0429 (11)0.0098 (9)0.0018 (9)−0.0003 (9)
C60.0355 (10)0.0470 (13)0.0482 (12)0.0008 (9)0.0089 (9)−0.0024 (10)
C70.0313 (9)0.0327 (11)0.0411 (10)−0.0025 (8)0.0052 (8)−0.0035 (8)
C80.0375 (10)0.0297 (10)0.0390 (10)0.0002 (8)0.0070 (8)0.0033 (8)
C90.0328 (9)0.0309 (10)0.0423 (10)0.0017 (8)0.0033 (8)−0.0024 (8)
C100.0455 (12)0.0419 (13)0.0490 (12)0.0112 (10)0.0031 (9)−0.0021 (10)
C110.0386 (10)0.0415 (11)0.0353 (10)0.0047 (9)0.0013 (8)−0.0021 (9)
C120.0349 (10)0.0369 (11)0.0448 (11)−0.0035 (8)0.0034 (8)−0.0078 (9)
O10.0392 (8)0.0791 (12)0.0768 (11)−0.0069 (8)0.0205 (8)0.0052 (9)
O20.0689 (11)0.0550 (10)0.0784 (11)0.0261 (8)0.0083 (9)0.0170 (9)
O30.0726 (11)0.0345 (9)0.0716 (11)0.0137 (7)0.0131 (8)0.0022 (8)
O40.0655 (10)0.0696 (11)0.0616 (10)−0.0019 (8)0.0328 (8)0.0038 (8)
O50.0326 (7)0.0582 (10)0.0685 (10)0.0107 (7)0.0044 (7)0.0018 (8)
O60.0500 (8)0.0464 (9)0.0516 (8)0.0096 (6)0.0161 (7)−0.0056 (7)

Geometric parameters (Å, °)

C1—O11.194 (2)C6—O61.386 (2)
C1—O51.384 (2)C6—C71.502 (3)
C1—C21.503 (3)C7—C81.545 (2)
C2—C91.533 (3)C7—H70.9800
C2—C31.546 (3)C8—C111.508 (3)
C2—H20.9800C8—C91.546 (3)
C3—C121.500 (3)C8—H80.9800
C3—C41.551 (2)C9—C101.502 (3)
C3—H30.9800C9—H90.9800
C4—C51.504 (3)C10—O21.188 (2)
C4—C71.532 (3)C10—O51.382 (3)
C4—H40.9800C11—C121.326 (3)
C5—O31.192 (2)C11—H110.9300
C5—O61.384 (2)C12—H120.9300
C6—O41.189 (2)
O1—C1—O5120.12 (18)C6—C7—C8111.21 (15)
O1—C1—C2129.6 (2)C4—C7—C8110.07 (15)
O5—C1—C2110.29 (18)C6—C7—H7110.3
C1—C2—C9104.20 (15)C4—C7—H7110.3
C1—C2—C3110.54 (15)C8—C7—H7110.3
C9—C2—C3109.79 (15)C11—C8—C7108.31 (15)
C1—C2—H2110.7C11—C8—C9107.83 (15)
C9—C2—H2110.7C7—C8—C9105.15 (14)
C3—C2—H2110.7C11—C8—H8111.7
C12—C3—C2107.81 (15)C7—C8—H8111.7
C12—C3—C4108.10 (15)C9—C8—H8111.7
C2—C3—C4105.96 (14)C10—C9—C2104.37 (15)
C12—C3—H3111.6C10—C9—C8110.90 (15)
C2—C3—H3111.6C2—C9—C8110.18 (14)
C4—C3—H3111.6C10—C9—H9110.4
C5—C4—C7104.15 (16)C2—C9—H9110.4
C5—C4—C3110.29 (15)C8—C9—H9110.4
C7—C4—C3109.89 (14)O2—C10—O5120.48 (18)
C5—C4—H4110.8O2—C10—C9129.2 (2)
C7—C4—H4110.8O5—C10—C9110.31 (17)
C3—C4—H4110.8C12—C11—C8114.96 (16)
O3—C5—O6119.82 (19)C12—C11—H11122.5
O3—C5—C4129.8 (2)C8—C11—H11122.5
O6—C5—C4110.36 (17)C11—C12—C3114.75 (17)
O4—C6—O6120.26 (19)C11—C12—H12122.6
O4—C6—C7129.5 (2)C3—C12—H12122.6
O6—C6—C7110.22 (17)C10—O5—C1110.67 (15)
C6—C7—C4104.49 (15)C5—O6—C6110.52 (16)
O1—C1—C2—C9−175.3 (2)C4—C7—C8—C9−62.20 (17)
O5—C1—C2—C93.2 (2)C1—C2—C9—C10−1.16 (19)
O1—C1—C2—C3−57.4 (3)C3—C2—C9—C10−119.57 (16)
O5—C1—C2—C3121.13 (17)C1—C2—C9—C8117.95 (15)
C1—C2—C3—C12−59.7 (2)C3—C2—C9—C8−0.46 (19)
C9—C2—C3—C1254.68 (18)C11—C8—C9—C1061.6 (2)
C1—C2—C3—C4−175.28 (15)C7—C8—C9—C10176.98 (15)
C9—C2—C3—C4−60.87 (18)C11—C8—C9—C2−53.47 (18)
C12—C3—C4—C559.5 (2)C7—C8—C9—C261.93 (17)
C2—C3—C4—C5174.86 (15)C2—C9—C10—O2176.5 (2)
C12—C3—C4—C7−54.75 (19)C8—C9—C10—O257.9 (3)
C2—C3—C4—C760.60 (18)C2—C9—C10—O5−1.2 (2)
C7—C4—C5—O3172.72 (19)C8—C9—C10—O5−119.86 (17)
C3—C4—C5—O354.9 (3)C7—C8—C11—C12−56.8 (2)
C7—C4—C5—O6−4.85 (19)C9—C8—C11—C1256.5 (2)
C3—C4—C5—O6−122.71 (16)C8—C11—C12—C30.4 (2)
O4—C6—C7—C4−177.8 (2)C2—C3—C12—C11−57.5 (2)
O6—C6—C7—C40.55 (19)C4—C3—C12—C1156.6 (2)
O4—C6—C7—C8−59.1 (3)O2—C10—O5—C1−174.58 (19)
O6—C6—C7—C8119.27 (16)C9—C10—O5—C13.4 (2)
C5—C4—C7—C62.49 (18)O1—C1—O5—C10174.51 (19)
C3—C4—C7—C6120.62 (15)C2—C1—O5—C10−4.2 (2)
C5—C4—C7—C8−117.01 (16)O3—C5—O6—C6−172.38 (18)
C3—C4—C7—C81.1 (2)C4—C5—O6—C65.5 (2)
C6—C7—C8—C11−62.4 (2)O4—C6—O6—C5174.79 (18)
C4—C7—C8—C1152.87 (19)C7—C6—O6—C5−3.7 (2)
C6—C7—C8—C9−177.52 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.982.503.313 (3)140
C8—H8···O3ii0.982.583.175 (2)119

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2233).

References

  • Bruker (2007). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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