The title compound, C31H24, with three molecules in the asymmetric unit. The crystal packing is mainly stabilized by weak C—H⋯π inter­actions in addition to van der Waals forces

Arslan, Mustafa

Asker, Erol

Baker, Ronald J.

Masnovi, John

English

Cleveland-Marshall College of Law

Cleveland State UniversityEngagedScholarship@CSUChemistry Faculty Publications Chemistry Department4-15-20071,3-Bi-9-anthrylpropaneMustafa ArslanSakarya University, Adapazari, TurkeyErol AskerBalıkesir University, Balıkesir, TurkeyJohn MasnoviCleveland State University, j.masnovi@csuohio.eduRonald J. BakerFollow this and additional works at: https://engagedscholarship.csuohio.edu/scichem_facpubPart of the Organic Chemistry CommonsHow does access to this work benefit you? Let us know!This Article is brought to you for free and open access by the Chemistry Department at EngagedScholarship@CSU. It has been accepted for inclusionin Chemistry Faculty Publications by an authorized administrator of EngagedScholarship@CSU. For more information, please contactlibrary.es@csuohio.edu.Recommended CitationArslan, M., Asker, E., Masnovi, J., & Baker, R. J. (2007). 1,3-bi-9-anthrylpropane. Acta Crystallographica Section E, 63(4),o1800-o1801. doi:10.1107/S1600536807010781organic paperso1800 Arslan et al.  C31H24 doi:10.1107/S1600536807010781 Acta Cryst. (2007). E63, o1800–o1801Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-53681,3-Bi-9-anthrylpropaneMustafa Arslan,a* Erol Asker,bJohn Masnovic and Ronald J.BakercaDepartment of Chemistry, Faculty of Arts andSciences, Sakarya University, 54140 Esentepe/Adapazari, Turkey, bNecatibey Faculty ofEducation, Balikesir University, 10100 Balikesir,Turkey, and cDepartment of Chemistry,Cleveland State University, Cleveland,OH 44115, USACorrespondence e-mail: marslan@sakarya.edu.trKey indicatorsSingle-crystal X-ray studyT = 295 KMean (C–C) = 0.006 A˚R factor = 0.044wR factor = 0.103Data-to-parameter ratio = 7.4For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e.Received 8 January 2007Accepted 7 March 2007# 2007 International Union of CrystallographyAll rights reservedThe title compound, C31H24, with three molecules in theasymmetric unit. The crystal packing is mainly stabilized byweak C—H   interactions in addition to van der Waalsforces.CommentBichromophoric model compounds of polyvinylanthracenesare extensively used in studies concerning the electrophoto-graphic properties of polymers (Hayashi et al., 1976; Becker &Andersson, 1987; Becker et al., 1992). In pendant-type poly-meric systems, photoconductivity depends largely on thespacing and orientation of the pendant units in the polymerbackbone. The molecular geometries of 9,90-bianthryl, bis-9-anthrylmethane (Becker et al., 1992) and 1,2-bis(9-anthryl)-ethane (Becker et al., 1984) were determined in order tounderstand their photochemical and photophysical properties.We report here the crystal structure of the title compound, (I)(Fig. 1), as the third member of this family of bichromophoricmodel compounds of polyvinylanthracenes.The crystal structure of compound (I) (Fig. 1) was solved inthe non-centrosymmetric space group P212121, with threeindependent molecules (A, B, and C) in the asymmetric unit.All six anthracene skeletons are essentially planar, the largestdeviation from planarity of the fitted atoms being 0.088 (4) A˚for atom C29b. The bond distances and angles of the anthra-cene rings in all three molecules are comparable with eachother and with those of related molecules (Becker et al., 1984,1992). The anthryl groups exhibit an anti–anti conformationalong the connecting aliphatic chains. The dihedral anglesformed by the anthracene planes are 61.00 (6) in molecule A,59.79 (6) in molecule B and 69.85 (5) in molecule C.The crystal packing diagram (Fig. 2) reveals that the crystalstructure of (I) is stabilized only by van der Waals forces andweak C—H   interactions (Table 1). Although moleculeswith aromatic groups often pack in the solid state with parallelplanar  systems, there are neither intra- nor intermolecular– interactions observed among the anthracene ring systemsof (I).ExperimentalThe title compound was prepared via LiAlH4/AlCl3 reduction of amixture of 1,3-bis(9-anthryl)propan-1-one and 1,3-bis(9-anthryl)-propan-1-ol, which were prepared according to the literature proce-dure (Becker & Andersson, 1983). First, AlCl3 (3.3 g, 25 mmol) indiethyl ether (40 ml) was added to a stirred solution of LiAlH4(0.95 g, 25 mmol) in diethyl ether (40 ml) in an ice bath, which wasremoved after the addition was complete. A mixture (2.15 g,5.25 mmol) of 1,3-bis(9-anthryl)propan-1-ol and 1,3-bis(9-anthryl)-propan-1-one (2:1 molar ratio) was dissolved in diethyl ether (50 ml)and a minimum amount of tetrahydrofuran (to increase solubility),and the solution was then added dropwise to the above LiAlH4/AlCl3mixture and the reaction mixture refluxed for 2 h. After cooling, ethylacetate (60 ml) and 20% H2SO4 (70 ml) were added to the reactionmixture to deactivate unreacted LiAlH4. The mixture was extractedwith dichloromethane and dried over sodium sulfate. The residueobtained after vacuum evaporation of the solvents was purified bycolumn chromatography on silica gel using hexane–dichloromethane(9:1 v/v) and crystallized from hexane–dichloromethane (1:1 v/v) togive 1.77 g (4.47 mmol, 82% yield) of (I) as yellow crystals (m.p. 468–469 K).Crystal dataC31H24Mr = 396.5Orthorhombic, P212121a = 13.478 (2) A˚b = 19.1167 (14) A˚c = 25.2951 (17) A˚V = 6517.5 (12) A˚3Z = 12Mo K radiation = 0.07 mm1T = 295 (2) K0.50  0.50  0.50 mmData collectionEnraf–Nonius CAD-4diffractometerAbsorption correction: none6228 measured reflections6228 independent reflections4061 reflections with I > 2(I)3 standard reflectionsfrequency: 120 minintensity decay: 0.7%RefinementR[F 2 > 2(F 2)] = 0.044wR(F 2) = 0.103S = 1.036228 reflections838 parametersH-atom parameters constrainedmax = 0.12 e A˚3min = 0.10 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AC2a—H2a  Cg1 0.93 2.86 3.5722 (5) 135C6c—H6c  Cg2i 0.93 2.95 3.8708 (4) 170C8b—H8b  Cg3ii 0.93 2.82 3.7438 (6) 173C8c—H8c  Cg4i 0.93 2.80 3.6815 (5) 159C17b—H17d  Cg5iii 0.97 2.90 3.8021 (4) 156C17c—H17e  Cg6ii 0.97 2.90 3.8054 (4) 155C23a—H23a  Cg7iv 0.93 2.59 3.5045 (5) 167Symmetry codes: (i) xþ 1; y; z; (ii) x 12;y þ 12;z; (iii) xþ 1; y 12;zþ 12; (iv)x; y þ 12;zþ 12.All H atoms were positioned geometrically and allowed to ride ontheir corresponding parent atoms, with C—H = 0.93 and 0.97 A˚ foraromatic and methylene H atoms, respectively, and with Uiso (H) =1.2Ueq(C).Data collection and cell refinement: CAD-4-PC Software (Enraf–Nonius, 1993); data reduction: DATRD2 in NRCVAX (Gabe et al.,1989); program(s) used to solve structure: SHELXS97 (Sheldrick,1997); program(s) used to refine structure: SHELXL97 (Sheldrick,1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software usedto prepare material for publication: WinGX (Farrugia, 1999).The authors acknowledge support recieved from theTurkish Ministry of Education and the CSU College ofGraduate Studies.ReferencesBecker, H. D. & Andersson, K. (1983). J. Org. Chem. 48, 4542–4549.Becker, H. D. & Andersson, K. (1987). J. Org. Chem. 52, 5205–5213.Becker, H. D., Langer, V., Sieler, J. & Becker, H. C. (1992). J. Org. Chem. 57,1883–1887.Becker, H., Engelhardt, L. M., Hansen, L., Patrick, V. A. & White, A. H.(1984). Aust. J. Chem. 37, 1329–1335.Enraf–Nonius (1993). CAD-4-PC Software. Version 1.2. Enraf–Nonius, Delft,The Netherlands.Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl.Cryst. 22, 384–387.Hayashi, T., Mataga, N., Sakata, Y., Misumi, S., Morita, M. & Tanaka, J. (1976).J. Am. Chem. Soc. 98, 5910–5913.Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University ofGo¨ttingen, Germany.organic papersActa Cryst. (2007). E63, o1800–o1801 Arslan et al.  C31H24 o1801Figure 1The three independent molecules of (I), with the atom-numberingscheme. Displacement ellipsoids are drawn at the 30% probability level.Figure 2The crystal packing of (I), viewed down the b axis. H atoms have beenomitted for clarity.

1,3-Bi-9-anthrylpropane

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1,3-Bi-9-anthrylpropane

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