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access2,3-Bis(furan-2-yl)pyrazino[2,3-f][1,10]phenanthroline
aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
*Correspondence e-mail: cgzheng@jiangnan.edu.cn
The molecule of the title compound, C22H12N4O2, is located on a twofold rotation axis. The dihedral angle between the furan and pyrazine rings is 34.8 (7)°, and that between the furan rings is 46.92 (7)°. A π–π stacking interaction occurs between adjacent pyrazino[2,3-f][1,10]phenanthroline units, with an interplanar distance of 3.5862 (12) Å.
CCDC reference: 962963
Related literature
For the properties of 2,3-dithienylpyrazino[2,3-f][1,10]phenanthroline, see: Bencini et al. (1999![[Bencini, A., Bernardo, M. A., Bianchi, A., Fusi, V., Giorgi, C., Pina, F. & Valtancoli, B. (1999). Eur. J. Inorg. Chem. pp. 1911-1918.]](../../../../../../logos/arrows/e_arr.gif "Bencini, A., Bernardo, M. A., Bianchi, A., Fusi, V., Giorgi, C., Pina, F. & Valtancoli, B. (1999). Eur. J. Inorg. Chem. pp. 1911-1918.")
); Li et al. (2010). For the structure of 2,3-bis(thiophen-2-yl)pyrazino[2,3-f][1,10]phenanthroline, see: Zheng et al. (2012) and for the structure of 3-carboxypyrazino[2,3-f][1,10]-phenanthrolin-9-ium-2-carboxylate see: Zhang et al. (2010).
![[Scheme 1]](bt6933scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 962963
contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681302641X/bt6933sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S160053681302641X/bt6933Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681302641X/bt6933Isup3.cml
The title compound was synthesized by using 1,10-phenanthroline and 2-furaldehyde as the starting material according to the published route (Li et al., 2010). The single crystals were obtained by recrystallization from the mixture of methanol and dichloromethane at room temperature.
All H atoms were located in a difference map but placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distance of 0.93 Å, and with Uiso(H)=1.2Uiso(C).
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).
![[Figure 1]](./bt6933fig1thm.gif) | Fig. 1. The asymmetric unit of the title complex showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| C22H12N4O2 | F(000) = 752 |
| Mr = 364.36 | Dx = 1.449 Mg m−3 |
| Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2n 2ab | Cell parameters from 6163 reflections |
| a = 7.0994 (14) Å | θ = 3.3–27.5° |
| b = 25.014 (5) Å | µ = 0.10 mm−1 |
| c = 9.4083 (19) Å | T = 293 K |
| V = 1670.8 (6) Å3 | Block, yellow |
| Z = 4 | 0.26 × 0.21 × 0.18 mm |
| Bruker APEXII CCD diffractometer | 1565 independent reflections |
| Radiation source: fine-focus sealed tube | 1382 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.035 |
| ϕ and ω scans | θmax = 25.5°, θmin = 3.3° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) | h = −8→8 |
| Tmin = 0.975, Tmax = 0.983 | k = −21→30 |
| 7791 measured reflections | l = −11→11 |
| 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.114 | H-atom parameters constrained |
| S = 1.18 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.3579P] where P = (Fo2 + 2Fc2)/3 |
| 1565 reflections | (Δ/σ)max < 0.001 |
| 127 parameters | Δρmax = 0.16 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C22H12N4O2 | V = 1670.8 (6) Å3 |
| Mr = 364.36 | Z = 4 |
| Orthorhombic, Pbcn | Mo Kα radiation |
| a = 7.0994 (14) Å | µ = 0.10 mm−1 |
| b = 25.014 (5) Å | T = 293 K |
| c = 9.4083 (19) Å | 0.26 × 0.21 × 0.18 mm |
| Bruker APEXII CCD diffractometer | 1565 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) | 1382 reflections with I > 2σ(I) |
| Tmin = 0.975, Tmax = 0.983 | Rint = 0.035 |
| 7791 measured reflections |
| R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
| wR(F2) = 0.114 | H-atom parameters constrained |
| S = 1.18 | Δρmax = 0.16 e Å−3 |
| 1565 reflections | Δρmin = −0.19 e Å−3 |
| 127 parameters |
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 | ||
| N1 | 0.14263 (19) | 0.43286 (5) | 0.35255 (15) | 0.0303 (4) | |
| C6 | 0.0687 (2) | 0.47894 (6) | 0.30306 (18) | 0.0284 (4) | |
| C2 | 0.1413 (2) | 0.52917 (6) | 0.35808 (18) | 0.0297 (4) | |
| O1 | 0.19388 (17) | 0.29767 (4) | 0.25670 (14) | 0.0391 (4) | |
| C3 | 0.2798 (2) | 0.53071 (7) | 0.46419 (19) | 0.0337 (4) | |
| H3 | 0.3250 | 0.4992 | 0.5038 | 0.040* | |
| C7 | 0.0756 (2) | 0.38724 (6) | 0.30014 (17) | 0.0295 (4) | |
| C1 | 0.0746 (2) | 0.57801 (6) | 0.30375 (18) | 0.0302 (4) | |
| N2 | 0.1436 (2) | 0.62587 (6) | 0.34706 (16) | 0.0373 (4) | |
| C8 | 0.1713 (2) | 0.33906 (6) | 0.35072 (18) | 0.0307 (4) | |
| C9 | 0.2526 (3) | 0.32685 (7) | 0.4760 (2) | 0.0377 (5) | |
| H9 | 0.2574 | 0.3483 | 0.5566 | 0.045* | |
| C4 | 0.3478 (3) | 0.57901 (7) | 0.5089 (2) | 0.0394 (5) | |
| H4 | 0.4396 | 0.5810 | 0.5792 | 0.047* | |
| C5 | 0.2760 (3) | 0.62534 (7) | 0.4462 (2) | 0.0408 (5) | |
| H5 | 0.3244 | 0.6580 | 0.4762 | 0.049* | |
| C11 | 0.2910 (3) | 0.25895 (7) | 0.3286 (2) | 0.0401 (5) | |
| H11 | 0.3254 | 0.2261 | 0.2904 | 0.048* | |
| C10 | 0.3295 (3) | 0.27471 (7) | 0.4608 (2) | 0.0401 (5) | |
| H10 | 0.3942 | 0.2553 | 0.5296 | 0.048* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0335 (8) | 0.0231 (7) | 0.0344 (8) | 0.0012 (6) | −0.0021 (6) | −0.0002 (6) |
| C6 | 0.0291 (8) | 0.0233 (8) | 0.0329 (9) | 0.0000 (7) | 0.0015 (7) | −0.0003 (7) |
| C2 | 0.0295 (8) | 0.0248 (9) | 0.0348 (9) | 0.0002 (6) | 0.0006 (7) | −0.0028 (7) |
| O1 | 0.0482 (7) | 0.0258 (6) | 0.0433 (7) | 0.0083 (5) | −0.0033 (6) | −0.0036 (5) |
| C3 | 0.0337 (9) | 0.0267 (9) | 0.0409 (10) | 0.0023 (7) | −0.0052 (8) | −0.0012 (7) |
| C7 | 0.0329 (8) | 0.0243 (8) | 0.0313 (9) | 0.0006 (7) | 0.0007 (7) | −0.0006 (7) |
| C1 | 0.0317 (8) | 0.0240 (8) | 0.0348 (9) | −0.0012 (7) | 0.0022 (7) | −0.0021 (7) |
| N2 | 0.0404 (8) | 0.0249 (8) | 0.0465 (9) | −0.0024 (6) | −0.0053 (7) | −0.0025 (6) |
| C8 | 0.0335 (9) | 0.0205 (8) | 0.0380 (10) | −0.0008 (6) | 0.0003 (8) | −0.0012 (7) |
| C9 | 0.0423 (10) | 0.0297 (10) | 0.0412 (10) | 0.0029 (8) | −0.0065 (9) | 0.0010 (8) |
| C4 | 0.0378 (10) | 0.0339 (10) | 0.0465 (11) | −0.0014 (8) | −0.0097 (8) | −0.0058 (8) |
| C5 | 0.0434 (10) | 0.0268 (10) | 0.0523 (12) | −0.0044 (8) | −0.0067 (9) | −0.0072 (8) |
| C11 | 0.0407 (10) | 0.0232 (9) | 0.0564 (12) | 0.0065 (8) | 0.0031 (9) | 0.0041 (8) |
| C10 | 0.0380 (10) | 0.0334 (11) | 0.0490 (12) | 0.0056 (8) | −0.0017 (9) | 0.0111 (9) |
| N1—C7 | 1.331 (2) | C1—N2 | 1.356 (2) |
| N1—C6 | 1.349 (2) | C1—C1i | 1.465 (3) |
| C6—C6i | 1.396 (3) | N2—C5 | 1.325 (2) |
| C6—C2 | 1.453 (2) | C8—C9 | 1.347 (2) |
| C2—C3 | 1.402 (2) | C9—C10 | 1.421 (2) |
| C2—C1 | 1.406 (2) | C9—H9 | 0.9300 |
| O1—C11 | 1.368 (2) | C4—C5 | 1.396 (3) |
| O1—C8 | 1.371 (2) | C4—H4 | 0.9300 |
| C3—C4 | 1.367 (2) | C5—H5 | 0.9300 |
| C3—H3 | 0.9300 | C11—C10 | 1.333 (3) |
| C7—C7i | 1.429 (3) | C11—H11 | 0.9300 |
| C7—C8 | 1.463 (2) | C10—H10 | 0.9300 |
| C7—N1—C6 | 117.74 (15) | C9—C8—O1 | 110.07 (15) |
| N1—C6—C6i | 121.24 (9) | C9—C8—C7 | 132.06 (16) |
| N1—C6—C2 | 118.53 (16) | O1—C8—C7 | 117.81 (14) |
| C6i—C6—C2 | 120.17 (10) | C8—C9—C10 | 106.51 (16) |
| C3—C2—C1 | 118.10 (15) | C8—C9—H9 | 126.7 |
| C3—C2—C6 | 121.75 (15) | C10—C9—H9 | 126.7 |
| C1—C2—C6 | 120.14 (16) | C3—C4—C5 | 118.34 (17) |
| C11—O1—C8 | 105.93 (14) | C3—C4—H4 | 120.8 |
| C4—C3—C2 | 119.40 (16) | C5—C4—H4 | 120.8 |
| C4—C3—H3 | 120.3 | N2—C5—C4 | 124.37 (16) |
| C2—C3—H3 | 120.3 | N2—C5—H5 | 117.8 |
| N1—C7—C7i | 120.87 (9) | C4—C5—H5 | 117.8 |
| N1—C7—C8 | 114.83 (15) | C10—C11—O1 | 110.82 (16) |
| C7i—C7—C8 | 124.29 (9) | C10—C11—H11 | 124.6 |
| N2—C1—C2 | 122.43 (16) | O1—C11—H11 | 124.6 |
| N2—C1—C1i | 117.94 (10) | C11—C10—C9 | 106.66 (16) |
| C2—C1—C1i | 119.63 (10) | C11—C10—H10 | 126.7 |
| C5—N2—C1 | 117.32 (15) | C9—C10—H10 | 126.7 |
| C7—N1—C6—C6i | −2.2 (3) | C1i—C1—N2—C5 | 178.75 (19) |
| C7—N1—C6—C2 | −179.43 (14) | C11—O1—C8—C9 | 0.52 (19) |
| N1—C6—C2—C3 | −2.5 (3) | C11—O1—C8—C7 | 178.19 (15) |
| C6i—C6—C2—C3 | −179.73 (19) | N1—C7—C8—C9 | 33.1 (3) |
| N1—C6—C2—C1 | 176.70 (15) | C7i—C7—C8—C9 | −148.3 (2) |
| C6i—C6—C2—C1 | −0.5 (3) | N1—C7—C8—O1 | −143.91 (15) |
| C1—C2—C3—C4 | −1.4 (3) | C7i—C7—C8—O1 | 34.7 (3) |
| C6—C2—C3—C4 | 177.83 (17) | O1—C8—C9—C10 | −0.5 (2) |
| C6—N1—C7—C7i | −2.9 (3) | C7—C8—C9—C10 | −177.69 (18) |
| C6—N1—C7—C8 | 175.76 (14) | C2—C3—C4—C5 | −0.1 (3) |
| C3—C2—C1—N2 | 2.1 (3) | C1—N2—C5—C4 | −0.3 (3) |
| C6—C2—C1—N2 | −177.09 (15) | C3—C4—C5—N2 | 1.0 (3) |
| C3—C2—C1—C1i | −177.92 (18) | C8—O1—C11—C10 | −0.4 (2) |
| C6—C2—C1—C1i | 2.9 (3) | O1—C11—C10—C9 | 0.1 (2) |
| C2—C1—N2—C5 | −1.3 (3) | C8—C9—C10—C11 | 0.2 (2) |
| Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
| Crystal data | |
| Chemical formula | C22H12N4O2 |
| Mr | 364.36 |
| Crystal system, space group | Orthorhombic, Pbcn |
| Temperature (K) | 293 |
| a, b, c (Å) | 7.0994 (14), 25.014 (5), 9.4083 (19) |
| V (Å3) | 1670.8 (6) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.10 |
| Crystal size (mm) | 0.26 × 0.21 × 0.18 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 2008a) |
| Tmin, Tmax | 0.975, 0.983 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7791, 1565, 1382 |
| Rint | 0.035 |
| (sin θ/λ)max (Å−1) | 0.606 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.114, 1.18 |
| No. of reflections | 1565 |
| No. of parameters | 127 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.16, −0.19 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).
Acknowledgements
The authors are grateful for financial support from the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
References
Bencini, A., Bernardo, M. A., Bianchi, A., Fusi, V., Giorgi, C., Pina, F. & Valtancoli, B. (1999). Eur. J. Inorg. Chem. pp. 1911–1918. CrossRef Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA. Google Scholar
Li, X. X., Guo, Y., Chi, H. J., Dong, Y. Z. & Hong, B. (2010). Mater. Chem. Phys. 123, 289–292. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X.-N., Fu, F., Li, D.-S. & Meng, C.-X. (2010). Acta Cryst. E66, o740. Web of Science CrossRef IUCr Journals Google Scholar
Zheng, C.-G., Kong, J., Zhang, P. & Dong, W.-X. (2012). Acta Cryst. E68, o1443. CSD CrossRef IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
2,3-Di(furan-2-yl)pyrazino[2,3-f][1,10]phenanthroline as a ligand has been extensively used as ligand in both analytical and preparative coordination chemistry (Bencini et al., 1999; Li et al. 2010), due to its rigid structure and fluorescence property.
The structure of 2,3-di(furan-2-yl)pyrazino[2,3-f][1,10]phenanthroline, C22H12N4O2, has orthorhombic (Pbcn) symmetry. The dihedral angles between the furan ring and the pyrazine ring is 34.77 (67)°.