Acta Cryst. (2008). E64, o1021 [ doi:10.1107/S1600536808012452 ]
In the title compound, C12H8O6, molecules are linked by weak C-H
O interactions involving all the potential donors, generating a three-dimensional network.
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.
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.
Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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).
![[Figure 1]](./sg2233fig1thm.gif)
| Fig. 1. Molecular structure showing 50% probability displacement ellipsoids. |
![[Figure 2]](./sg2233fig2thm.gif)
| Fig. 2. Packing diagram viewed down the a axis. |
| C12H8O6 | F000 = 512 |
| Mr = 248.18 | Dx = 1.613 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2677 reflections |
| a = 7.627 (2) Å | θ = 2.9–24.1º |
| b = 13.877 (3) Å | µ = 0.13 mm−1 |
| c = 9.823 (2) Å | T = 296 (2) K |
| β = 100.68 (2)º | Prism, colourless |
| V = 1021.7 (4) Å3 | 0.28 × 0.16 × 0.10 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 2119 independent reflections |
| Radiation source: fine-focus sealed tube | 1460 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.051 |
| T = 296(2) K | θmax = 26.5º |
| φ and ω scans | θmin = 2.6º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
| Tmin = 0.921, Tmax = 0.987 | k = −17→15 |
| 11412 measured reflections | l = −11→12 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-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 = 1.01 | Δρmax = 0.21 e Å−3 |
| 2118 reflections | Δρmin = −0.16 e Å−3 |
| 164 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.005 (1) |
| Secondary atom site location: difference Fourier map |
| C12H8O6 | V = 1021.7 (4) Å3 |
| Mr = 248.18 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 7.627 (2) Å | µ = 0.13 mm−1 |
| b = 13.877 (3) Å | T = 296 (2) K |
| c = 9.823 (2) Å | 0.28 × 0.16 × 0.10 mm |
| β = 100.68 (2)º |
| Bruker SMART CCD area-detector diffractometer | 2119 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1460 reflections with I > 2σ(I) |
| Tmin = 0.921, Tmax = 0.987 | Rint = 0.051 |
| 11412 measured reflections |
| R[F2 > 2σ(F2)] = 0.042 | 164 parameters |
| wR(F2) = 0.099 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 0.21 e Å−3 |
| 2118 reflections | Δρmin = −0.16 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.7820 (3) | 0.83700 (16) | 0.6304 (2) | 0.0449 (5) | |
| C2 | 0.5829 (2) | 0.84372 (13) | 0.61717 (19) | 0.0355 (4) | |
| H2 | 0.5239 | 0.8381 | 0.5200 | 0.043* | |
| C3 | 0.5305 (2) | 0.93909 (13) | 0.68048 (19) | 0.0350 (4) | |
| H3 | 0.5646 | 0.9952 | 0.6307 | 0.042* | |
| C4 | 0.3256 (2) | 0.93415 (13) | 0.67248 (18) | 0.0344 (4) | |
| H4 | 0.2633 | 0.9301 | 0.5760 | 0.041* | |
| C5 | 0.2627 (3) | 1.01999 (15) | 0.7435 (2) | 0.0416 (5) | |
| C6 | 0.1858 (3) | 0.89126 (15) | 0.8635 (2) | 0.0434 (5) | |
| C7 | 0.2788 (2) | 0.84782 (13) | 0.75613 (18) | 0.0352 (4) | |
| H7 | 0.1984 | 0.8039 | 0.6962 | 0.042* | |
| C8 | 0.4506 (2) | 0.79445 (13) | 0.82409 (18) | 0.0354 (4) | |
| H8 | 0.4251 | 0.7413 | 0.8831 | 0.042* | |
| C9 | 0.5347 (2) | 0.75817 (13) | 0.70190 (19) | 0.0358 (4) | |
| H9 | 0.4526 | 0.7145 | 0.6429 | 0.043* | |
| C10 | 0.7097 (3) | 0.70890 (16) | 0.7535 (2) | 0.0462 (5) | |
| C11 | 0.5767 (2) | 0.86683 (14) | 0.90425 (19) | 0.0392 (5) | |
| H11 | 0.6221 | 0.8602 | 0.9984 | 0.047* | |
| C12 | 0.6180 (2) | 0.94061 (14) | 0.83043 (19) | 0.0394 (5) | |
| H12 | 0.6951 | 0.9895 | 0.8686 | 0.047* | |
| O1 | 0.88296 (19) | 0.89053 (13) | 0.58906 (17) | 0.0638 (5) | |
| O2 | 0.7409 (2) | 0.64134 (12) | 0.82843 (18) | 0.0681 (5) | |
| O3 | 0.2829 (2) | 1.10382 (11) | 0.72476 (16) | 0.0596 (4) | |
| O4 | 0.1289 (2) | 0.85316 (12) | 0.95463 (16) | 0.0629 (5) | |
| O5 | 0.84589 (17) | 0.75576 (11) | 0.70513 (15) | 0.0537 (4) | |
| O6 | 0.17498 (18) | 0.99043 (10) | 0.84767 (14) | 0.0485 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0359 (11) | 0.0528 (13) | 0.0462 (12) | 0.0033 (10) | 0.0079 (9) | −0.0067 (10) |
| C2 | 0.0311 (9) | 0.0378 (11) | 0.0373 (10) | 0.0016 (8) | 0.0054 (7) | −0.0023 (8) |
| C3 | 0.0334 (9) | 0.0298 (10) | 0.0422 (10) | −0.0030 (8) | 0.0076 (8) | 0.0016 (8) |
| C4 | 0.0337 (9) | 0.0331 (10) | 0.0351 (9) | 0.0039 (8) | 0.0031 (7) | −0.0014 (8) |
| C5 | 0.0405 (11) | 0.0389 (12) | 0.0429 (11) | 0.0098 (9) | 0.0018 (9) | −0.0003 (9) |
| C6 | 0.0355 (10) | 0.0470 (13) | 0.0482 (12) | 0.0008 (9) | 0.0089 (9) | −0.0024 (10) |
| C7 | 0.0313 (9) | 0.0327 (11) | 0.0411 (10) | −0.0025 (8) | 0.0052 (8) | −0.0035 (8) |
| C8 | 0.0375 (10) | 0.0297 (10) | 0.0390 (10) | 0.0002 (8) | 0.0070 (8) | 0.0033 (8) |
| C9 | 0.0328 (9) | 0.0309 (10) | 0.0423 (10) | 0.0017 (8) | 0.0033 (8) | −0.0024 (8) |
| C10 | 0.0455 (12) | 0.0419 (13) | 0.0490 (12) | 0.0112 (10) | 0.0031 (9) | −0.0021 (10) |
| C11 | 0.0386 (10) | 0.0415 (11) | 0.0353 (10) | 0.0047 (9) | 0.0013 (8) | −0.0021 (9) |
| C12 | 0.0349 (10) | 0.0369 (11) | 0.0448 (11) | −0.0035 (8) | 0.0034 (8) | −0.0078 (9) |
| O1 | 0.0392 (8) | 0.0791 (12) | 0.0768 (11) | −0.0069 (8) | 0.0205 (8) | 0.0052 (9) |
| O2 | 0.0689 (11) | 0.0550 (10) | 0.0784 (11) | 0.0261 (8) | 0.0083 (9) | 0.0170 (9) |
| O3 | 0.0726 (11) | 0.0345 (9) | 0.0716 (11) | 0.0137 (7) | 0.0131 (8) | 0.0022 (8) |
| O4 | 0.0655 (10) | 0.0696 (11) | 0.0616 (10) | −0.0019 (8) | 0.0328 (8) | 0.0038 (8) |
| O5 | 0.0326 (7) | 0.0582 (10) | 0.0685 (10) | 0.0107 (7) | 0.0044 (7) | 0.0018 (8) |
| O6 | 0.0500 (8) | 0.0464 (9) | 0.0516 (8) | 0.0096 (6) | 0.0161 (7) | −0.0056 (7) |
| C1—O1 | 1.194 (2) | C6—O6 | 1.386 (2) |
| C1—O5 | 1.384 (2) | C6—C7 | 1.502 (3) |
| C1—C2 | 1.503 (3) | C7—C8 | 1.545 (2) |
| C2—C9 | 1.533 (3) | C7—H7 | 0.9800 |
| C2—C3 | 1.546 (3) | C8—C11 | 1.508 (3) |
| C2—H2 | 0.9800 | C8—C9 | 1.546 (3) |
| C3—C12 | 1.500 (3) | C8—H8 | 0.9800 |
| C3—C4 | 1.551 (2) | C9—C10 | 1.502 (3) |
| C3—H3 | 0.9800 | C9—H9 | 0.9800 |
| C4—C5 | 1.504 (3) | C10—O2 | 1.188 (2) |
| C4—C7 | 1.532 (3) | C10—O5 | 1.382 (3) |
| C4—H4 | 0.9800 | C11—C12 | 1.326 (3) |
| C5—O3 | 1.192 (2) | C11—H11 | 0.9300 |
| C5—O6 | 1.384 (2) | C12—H12 | 0.9300 |
| C6—O4 | 1.189 (2) | ||
| O1—C1—O5 | 120.12 (18) | C6—C7—C8 | 111.21 (15) |
| O1—C1—C2 | 129.6 (2) | C4—C7—C8 | 110.07 (15) |
| O5—C1—C2 | 110.29 (18) | C6—C7—H7 | 110.3 |
| C1—C2—C9 | 104.20 (15) | C4—C7—H7 | 110.3 |
| C1—C2—C3 | 110.54 (15) | C8—C7—H7 | 110.3 |
| C9—C2—C3 | 109.79 (15) | C11—C8—C7 | 108.31 (15) |
| C1—C2—H2 | 110.7 | C11—C8—C9 | 107.83 (15) |
| C9—C2—H2 | 110.7 | C7—C8—C9 | 105.15 (14) |
| C3—C2—H2 | 110.7 | C11—C8—H8 | 111.7 |
| C12—C3—C2 | 107.81 (15) | C7—C8—H8 | 111.7 |
| C12—C3—C4 | 108.10 (15) | C9—C8—H8 | 111.7 |
| C2—C3—C4 | 105.96 (14) | C10—C9—C2 | 104.37 (15) |
| C12—C3—H3 | 111.6 | C10—C9—C8 | 110.90 (15) |
| C2—C3—H3 | 111.6 | C2—C9—C8 | 110.18 (14) |
| C4—C3—H3 | 111.6 | C10—C9—H9 | 110.4 |
| C5—C4—C7 | 104.15 (16) | C2—C9—H9 | 110.4 |
| C5—C4—C3 | 110.29 (15) | C8—C9—H9 | 110.4 |
| C7—C4—C3 | 109.89 (14) | O2—C10—O5 | 120.48 (18) |
| C5—C4—H4 | 110.8 | O2—C10—C9 | 129.2 (2) |
| C7—C4—H4 | 110.8 | O5—C10—C9 | 110.31 (17) |
| C3—C4—H4 | 110.8 | C12—C11—C8 | 114.96 (16) |
| O3—C5—O6 | 119.82 (19) | C12—C11—H11 | 122.5 |
| O3—C5—C4 | 129.8 (2) | C8—C11—H11 | 122.5 |
| O6—C5—C4 | 110.36 (17) | C11—C12—C3 | 114.75 (17) |
| O4—C6—O6 | 120.26 (19) | C11—C12—H12 | 122.6 |
| O4—C6—C7 | 129.5 (2) | C3—C12—H12 | 122.6 |
| O6—C6—C7 | 110.22 (17) | C10—O5—C1 | 110.67 (15) |
| C6—C7—C4 | 104.49 (15) | C5—O6—C6 | 110.52 (16) |
| O1—C1—C2—C9 | −175.3 (2) | C4—C7—C8—C9 | −62.20 (17) |
| O5—C1—C2—C9 | 3.2 (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—C3 | 121.13 (17) | C1—C2—C9—C8 | 117.95 (15) |
| C1—C2—C3—C12 | −59.7 (2) | C3—C2—C9—C8 | −0.46 (19) |
| C9—C2—C3—C12 | 54.68 (18) | C11—C8—C9—C10 | 61.6 (2) |
| C1—C2—C3—C4 | −175.28 (15) | C7—C8—C9—C10 | 176.98 (15) |
| C9—C2—C3—C4 | −60.87 (18) | C11—C8—C9—C2 | −53.47 (18) |
| C12—C3—C4—C5 | 59.5 (2) | C7—C8—C9—C2 | 61.93 (17) |
| C2—C3—C4—C5 | 174.86 (15) | C2—C9—C10—O2 | 176.5 (2) |
| C12—C3—C4—C7 | −54.75 (19) | C8—C9—C10—O2 | 57.9 (3) |
| C2—C3—C4—C7 | 60.60 (18) | C2—C9—C10—O5 | −1.2 (2) |
| C7—C4—C5—O3 | 172.72 (19) | C8—C9—C10—O5 | −119.86 (17) |
| C3—C4—C5—O3 | 54.9 (3) | C7—C8—C11—C12 | −56.8 (2) |
| C7—C4—C5—O6 | −4.85 (19) | C9—C8—C11—C12 | 56.5 (2) |
| C3—C4—C5—O6 | −122.71 (16) | C8—C11—C12—C3 | 0.4 (2) |
| O4—C6—C7—C4 | −177.8 (2) | C2—C3—C12—C11 | −57.5 (2) |
| O6—C6—C7—C4 | 0.55 (19) | C4—C3—C12—C11 | 56.6 (2) |
| O4—C6—C7—C8 | −59.1 (3) | O2—C10—O5—C1 | −174.58 (19) |
| O6—C6—C7—C8 | 119.27 (16) | C9—C10—O5—C1 | 3.4 (2) |
| C5—C4—C7—C6 | 2.49 (18) | O1—C1—O5—C10 | 174.51 (19) |
| C3—C4—C7—C6 | 120.62 (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—C8 | 1.1 (2) | C4—C5—O6—C6 | 5.5 (2) |
| C6—C7—C8—C11 | −62.4 (2) | O4—C6—O6—C5 | 174.79 (18) |
| C4—C7—C8—C11 | 52.87 (19) | C7—C6—O6—C5 | −3.7 (2) |
| C6—C7—C8—C9 | −177.52 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O2i | 0.98 | 2.50 | 3.313 (3) | 140 |
| C8—H8···O3ii | 0.98 | 2.58 | 3.175 (2) | 119 |
| Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O2i | 0.98 | 2.50 | 3.313 (3) | 140 |
| C8—H8···O3ii | 0.98 | 2.58 | 3.175 (2) | 119 |
| Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2. |
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 Northern University of China.
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.
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.