Crystal structure of 1,2-di­benzoyl­ace­naphthyl­ene

Fred H Greenberg; Alexander Y Nazarenko

doi:10.1107/S2056989015011160

. 2015 Jun 13;71(Pt 7):o487–o488. doi: 10.1107/S2056989015011160

Crystal structure of 1,2-dibenzoylacenaphthylene

Fred H Greenberg ^a, Alexander Y Nazarenko ^a,^*

PMCID: PMC4518958 PMID: 26279922

Abstract

The title molecule, C₂₆H₁₆O₂, crystallizes as a molecular crystal with no strong intermolecular interactions (the shortest C—H⋯O contact is longer than 3.4 Å). Two flat acenaphthylene groups of neigboring 1,2-dibenzoylacenaphthylene molecules are related by a crystallographic center of symmetry and are stacked with the distance between their mean planes of 3.37 (1) Å, apparently making an optimal close packing for these bulky aromatic moieties. Both carbonyl groups are oriented towards the same side of the planar acenaphthylene. The angles between the flat acenaphthylene group and the benzoyl groups are 62.6 (1) and 57.8 (1)°. Because rotation of the benzoyl groups is sterically hindered, we expect that the molecules will remain locked in this ‘pseudo-cis’ orientation in solution. As a result, reduction of 1,2-dibenzoylacenaphthylene at low temperature with sodium dithionite yields the cis-isomer of 1,2-dibenzoyl-1,2-dihydroacenaphthylene, which is sterically favorable. This isomer is thermodynamically less favorable than the trans isomer, but it converts to the more stable isomer only on long-term heating (Greenberg & Schenendorf (1980 ▸).

Keywords: crystal structure; 1,2-dibenzoylacenaphthylene; crystal packing

Related literature

For synthesis and reactions of the title compound, see: Greenberg & Schenendorf (1980 ▸); Dilthey et al. (1938 ▸). For packing in molecular crystals of polyaromatic compounds, see: Kitaigorodsky (1973 ▸). graphic file with name e-71-0o487-scheme1.jpg

Experimental

Crystal data

C₂₆H₁₆O₂
M _r = 360.39
Triclinic,
a = 9.4578 (4) Å
b = 10.2665 (5) Å
c = 10.9183 (4) Å
α = 71.448 (2)°
β = 66.494 (2)°
γ = 84.269 (2)°
V = 921.21 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.69 × 0.65 × 0.41 mm

Data collection

Bruker PHOTON-100 CMOS diffractometer
Absorption correction: numerical (SADABS2014/5; Bruker, 2014 ▸) T _min = 0.867, T _max = 0.951
32789 measured reflections
4661 independent reflections
3721 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.119
S = 1.05
4661 reflections
317 parameters
All H-atom parameters refined
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015b ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015011160/zl2628sup1.cif

e-71-0o487-sup1.cif^{(1.1MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011160/zl2628Isup2.hkl

e-71-0o487-Isup2.hkl^{(371.1KB, hkl)}

Click here for additional data file.^{(3.4KB, cdx)}

Supporting information file. DOI: 10.1107/S2056989015011160/zl2628Isup3.cdx

Supporting information file. DOI: 10.1107/S2056989015011160/zl2628Isup4.txt

e-71-0o487-Isup4.txt^{(1.5KB, txt)}

Click here for additional data file.^{(1.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015011160/zl2628Isup5.cml

Click here for additional data file.^{(2.1MB, tif)}

. DOI: 10.1107/S2056989015011160/zl2628fig1.tif

The molecular structure of the title compound. Dispalcement elipsoids are drawn at 50% probability level.

Click here for additional data file.^{(1.8MB, tif)}

x y z . DOI: 10.1107/S2056989015011160/zl2628fig2.tif

Two "stacked" molecules of the title compound (symmetry operator −x, 1 − y, 2 − z). View along the perpendicular to the mean plane of acenaphthylene ring. The center of symmetry is shown in blue.

CCDC reference: 1405661

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from State University of New York (IITG grant No.880030) is gratefully acknowledged.

supplementary crystallographic information

S1. Synthesis and crystallization

Synthesis of the title compound is described in Greenberg & Schenendorf (1980).

S2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

All hydrogen atoms were located in electron difference density Fourier maps and were refined in an isotropic approximation.