1-Methyl-4-[(1E)-2-nitro­prop-1-en-1-yl]benzene

Zhao-Bo Li; Li-Li Shen; Jian-An Zheng

doi:10.1107/S1600536812025913

. 2012 Jun 13;68(Pt 7):o2065. doi: 10.1107/S1600536812025913

1-Methyl-4-[(1E)-2-nitroprop-1-en-1-yl]benzene

Zhao-Bo Li ^a,^b,^*, Li-Li Shen ^b, Jian-An Zheng ^c

PMCID: PMC3393329 PMID: 22807886

Abstract

The title compound, C₁₀H₁₁NO₂, adopts an E conformation about the C=C bond. The C=C—C=C torsion angle is 32.5 (3)°. The crystal structure features weak intermolecular C—H⋯O interactions.

Related literature

For background to the chemistry of nitroalkenes, see: Ballini & Petrini (2004 ▶); Berner et al. (2002 ▶); Ono (2001 ▶). For a related structure, see: Yang et al. (2010 ▶).

Experimental

Crystal data

C₁₀H₁₁NO₂
M _r = 177.20
Orthorhombic,
a = 11.0610 (5) Å
b = 7.5840 (4) Å
c = 22.6420 (11) Å
V = 1899.36 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.58 × 0.43 × 0.36 mm

Data collection

Rigaku R-AXIS-RAPID/ZJUG diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.941, T _max = 0.969
16972 measured reflections
2162 independent reflections
1325 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.134
S = 1.00
2162 reflections
121 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812025913/zq2167sup1.cif

e-68-o2065-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025913/zq2167Isup2.hkl

e-68-o2065-Isup2.hkl^{(104.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025913/zq2167Isup3.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
C8—H8⋯O1ⁱ	0.93	2.55	3.369 (2)	147
C2—H2⋯O2ⁱⁱ	0.93	2.66	3.551 (3)	162

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Mr Jianming Gu for the single-crystal X-ray analysis. They are also grateful for financial support from the State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology of Zhejiang University of Technology (GCTKF2012010).

supplementary crystallographic information

Comment

Nitroalkenes are important organic intermediates, since they can be converted to synthetically useful N- and O-containing organic molecules, such as amines, aldehydes, carboxylic acids, or denitrated compounds (Ono, 2001; Berner et al., 2002; Ballini & Petrini, 2004). As a contribution in this field, we have synthesized a series of nitroalkenes by employing benzaldehydes and nitroethane (Yang et al., 2010). We report here the crystal structure of the title compound (Fig. 1).

The molecule adopts an E configuration with respect to the C8=C9 double bond. The torsion angle C9—C8—C1—C6 is 32.5 (3)°. In the crystal structure, the molecules interact through weak intermolecular C8—H8···O1ⁱ and C2—H2···O2ⁱⁱ hydrogen bonds (symmetry codes: i = -x+1, -y, -z+1; ii = x+1/2, -y+1/2, -z+1; Fig. 2 and Table 1).

Experimental

To a solution of p-tolualdehyde (50 mmol) in AcOH (25 mL), nitroethane (75 mmol) was added, followed by butylamine (100 mmol, 7.4 mL). The mixture was sonicated at 60 °C, until GC showed full conversion of the aldehyde. The mixture was poured into ice water, the precipitate was filtered off, washed with water and recrystallized from EtOH/EtOAc to give the final product. Single crystals were obtained by slow evaporation of a n-hexane/EtOAc (10:1, v/v) solution.