1,3,5-Tri-p-tolyl­pentane-1,5-dione

You-Liang Shen

doi:10.1107/S1600536808036854

. 2008 Nov 13;64(Pt 12):o2330. doi: 10.1107/S1600536808036854

1,3,5-Tri-p-tolylpentane-1,5-dione

You-Liang Shen ^a,^*

PMCID: PMC2959968 PMID: 21581305

Abstract

In the crystal structure of the title compound, C₂₆H₂₆O₂, the dihedral angle between the tolyl rings at each end of the 1,5-dione chain is 70.3 (1)°; the tolyl group at the middle of the chain makes dihedral angles of 67.8 (2) and 85.1 (2)° with the terminal rings. One benzene C atom and one methylene C atom interact with a carbonyl O atom of an adjacent molecule through C—H⋯O hydrogen bonds, forming chains in the crystal.

Related literature

For the details of related structures, see: Burroughes et al. (1990 ▶); Smith et al. (2005 ▶); Li et al. (2004 ▶); Sariciftci et al. (1992 ▶). For the synthesis of the title compound, see: Yang et al. (2005 ▶).

Experimental

Crystal data

C₂₆H₂₆O₂
M _r = 370.47
Orthorhombic,
a = 10.6611 (19) Å
b = 10.3876 (18) Å
c = 19.541 (3) Å
V = 2164.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 (2) K
0.34 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.991
8705 measured reflections
2138 independent reflections
1733 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.135
S = 1.06
2138 reflections
256 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036854/wn2290sup1.cif

e-64-o2330-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036854/wn2290Isup2.hkl

e-64-o2330-Isup2.hkl^{(105.2KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2ⁱ	0.93	2.46	3.381 (5)	171 (1)
C18—H18A⋯O2ⁱ	0.97	2.52	3.460 (5)	164 (1)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks Jiangxi Science and Technology Normal University for supporting this study.

supplementary crystallographic information

Comment

Over the past several decades, linear π-conjugated organic molecules and polymers have attracted considerable interest because of their many promising applications, such as for organic light-emitting diodes, non-linear optical properties, conductivity, photocells, field-effect transistors, and so on, due to their delocalized π systems (Burroughes et al., 1990; Smith et al., 2005; Li et al., 2004; Sariciftci et al., 1992). In the course of our synthesis of the π-conjugated organic molecule, 2,4,6-tri-p-tolyl-pyridine, we synthesized the 1,5-dione intermediate 1,3,5-tri-p-tolyl-pentane-1,5-dione; the 1,5-dione intermediate was then cyclized by adding concentrated aqueous ammonia. We report here the crystal structure of the 1,5-dione intermediate, 1,3,5-tri-p-tolyl-pentane-1,5-dione.

As shown in Fig. 1, the title molecule is non-planar, and the dihedral angles between each pair of the three tolyl rings are 67.8 (2)° [C2–C7, C11–C16], 70.3 (1 ° [C11–C16, C20–C25] and 85.1 (2)° [C2–C7, C20–C25]. The C—C, C_ar—C_ar and C═O bond lengths are within their normal ranges. One benzene C atom (C7) and one methylene C atom (C18) interact with a carbonyl group O atom (O2) of an adjacent molecule through C—H···O hydrogen bonds [3.381 (5) Å, 3.460 (5) Å] to form a one-dimensional supramolecular array (Fig. 2).

Experimental

The title compound was synthesized according to a modified procedure (Yang et al., 2005). 4-Methylacetophenone (0.5 g, 4 mmol), 1,3-di-p-tolyl-propenone (0.9 g, 4 mmol) and powdered NaOH (0.6 g, 15 mmol) were crushed together for 2 h, using a pestle and mortar. Recrystallization from ethanol gave colorless prismatic crystals. Yield: 1.2 g (88%).