N-(2-Methyl-3-oxo-1,3-diphenyl­prop­yl)acetamide

Deli Yang; Daxin Shi; Qi Zhang; Hongxin Chai; Jiarong Li

doi:10.1107/S1600536813007320

. 2013 Apr 5;69(Pt 5):o633. doi: 10.1107/S1600536813007320

N-(2-Methyl-3-oxo-1,3-diphenylpropyl)acetamide

Deli Yang ^a, Daxin Shi ^a, Qi Zhang ^a, Hongxin Chai ^a, Jiarong Li ^a,^*

PMCID: PMC3647834 PMID: 23723800

Abstract

In the title compound, C₁₈H₁₉NO₂, the dihedral angle between the benzene rings is 42.0 (1)°. In the crystal, molecules are linked by N—H⋯O and C—H⋯π interactions.

Related literature

For the biological properties of N-(2-methyl-3-oxo-1,3-diphenylpropyl)acetamide derivatives, see: Barluenga et al. (1993 ▶); Casimir et al. (1995 ▶) and for their synthesis, see: Dakin & West (1928 ▶); Selvam & Perumal (2009 ▶); Heravi et al. (2009 ▶). graphic file with name e-69-0o633-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₉NO₂
M _r = 281.34
Monoclinic,
a = 9.156 (5) Å
b = 17.668 (8) Å
c = 10.103 (5) Å
β = 107.914 (7)°
V = 1555.0 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 K
0.61 × 0.07 × 0.02 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T _min = 0.954, T _max = 0.998
12600 measured reflections
3028 independent reflections
2386 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.156
S = 1.00
3028 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku/MSC, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Click here for additional data file.^{(24.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007320/lx2279sup1.cif

e-69-0o633-sup1.cif^{(24.5KB, cif)}

Click here for additional data file.^{(148.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007320/lx2279Isup2.hkl

e-69-0o633-Isup2.hkl^{(148.6KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813007320/lx2279Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.94 (3)	1.98 (3)	2.874 (3)	158 (2)
C1—H1⋯Cg1ⁱ	0.95	2.85 (1)	3.649 (3)	142 (1)
C16—H16A⋯Cg2ⁱⁱ	0.98	2.98 (1)	3.472 (3)	112 (1)

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

Acknowledgments

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

supplementary crystallographic information

Comment

N–(2–methyl–3–oxo–1,3–diphenylpropyl)acetamide is a class of 2–acetamino carbonyl compounds which exhibit great importance of biological (Casimir et al., 1995) and pharmacological (Barluenga et al., 1993) properties. Here, we report the crystal structure of the title compound. In the title molecule (Fig. 1), the dihedral angle formed by the benzene rings is 42.0°, and the methyl and the acetamide groups have an anti–conformation. In the crystal structure (Fig. 2), molecules are connected by N—H···O and C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C10–C15 benzene ring and the C1–C6 benzene ring, respectively).

Experimental

A solution of benzaldehyde (2 mmol) and propiophenone (2 mmol) in the presence of acetyl chloride and TiCl₄ was stirred in acetonitrile (5 ml) at room teperature for 3 h. The reaction mixture was poured to room temperature and then filtered to give the title compound. The product was recrystallizated from petrolum ether and ethyl acetate to give white crystalline powder. m.p. 439–441 K.