1,3-Bis(4-tert-butyl­phen­yl)-4-nitro­butan-1-one

Dong-Yin Ren; Lu Shi; Qin Zhang; Yi Xu; Hong-Jun Zhu

doi:10.1107/S1600536811018277

. 2011 May 20;67(Pt 6):o1465. doi: 10.1107/S1600536811018277

1,3-Bis(4-tert-butylphenyl)-4-nitrobutan-1-one

Dong-Yin Ren ^a, Lu Shi ^a, Qin Zhang ^a, Yi Xu ^a, Hong-Jun Zhu ^a,^*

PMCID: PMC3120520 PMID: 21754836

Abstract

In the crystal structure of the title compound, C₂₄H₃₁NO₃, molecules are connected via C—H⋯O intermolecular hydrogen bonds, forming dimers. The benzene rings are oriented at a dihedral angle of 29.8 (1)°.

Related literature

For applications of the title compound, see: Gorman et al. (2004 ▶). For a related structure, see: Hall et al. (2005 ▶). For the synthesis of the title compound, see: Liang et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₃₁NO₃
M _r = 381.50
Orthorhombic,
a = 20.440 (4) Å
b = 17.500 (4) Å
c = 6.1630 (12) Å
V = 2204.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.985, T _max = 0.993
8662 measured reflections
2247 independent reflections
1527 reflections with I > 2σ(I)
R _int = 0.096
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.181
S = 1.00
2247 reflections
247 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CAD-4 Software (Enraf-Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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/S1600536811018277/bq2291sup1.cif

e-67-o1465-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018277/bq2291Isup2.hkl

e-67-o1465-Isup2.hkl^{(110.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018277/bq2291Isup3.cml

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
C12—H12A⋯O1ⁱ	0.97	2.52	3.072 (5)	116

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The tittle compound, 1,3-bis(4-tert-butylphenyl)-4-nitrobutan-1-one is an important intermediate (Gorman et al., 2004) for the synthesis of 2,4-bis(4-tert-butylphenyl)-4-oxobutanal, which can be used to synthesis 2,4-bis(4-tert-butylphenyl)-1H-pyrrole(Hall et al., 2005). We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the rings (C5—C10) and (C15—C20) is 29.8 (1)°. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The molecules of (I) were connected together via C—H···O intermolecular hydrogen bonds to form molecular dimers (Table 1. and Fig. 2.).

Experimental

The title compound, (I) was prepared by the method of Michael reaction reported in literature (Liang et al., 2006). The crystals were obtained by dissolving (I) (0.2 g, 0.52 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d.