N-Benzyl-N-(4-chloro­phen­yl)acrylamide

Yi-Min Hu; Li-Dong Zhang; Jing Wang; Dong Cheng; Dong Ren

doi:10.1107/S160053680706432X

. 2007 Dec 6;64(Pt 1):o206. doi: 10.1107/S160053680706432X

N-Benzyl-N-(4-chlorophenyl)acrylamide

Yi-Min Hu ^a,^*, Li-Dong Zhang ^a, Jing Wang ^a, Dong Cheng ^a, Dong Ren ^a

PMCID: PMC2915267 PMID: 21200771

Abstract

In the molecular structure of the title compound, C₁₆H₁₄ClNO, the acrylamide unit is essentially planar and makes dihedral angles of 80.06 (12) and 68.91 (13)°, respectively, with the benzene and phenyl rings. The dihedral angle between the two rings is 49.79 (11)°. In the crystal structure, molecules are connected via weak C—H⋯O and C—H⋯π interactions, forming a molecular tape running along the b axis.

Related literature

For related literature, see: Fairlamb (2004 ▶); Hu et al. (2003 ▶); Park & Hoffmann (1990 ▶); Otero & Cantero (1995 ▶); Riggi et al. (1992 ▶).

Experimental

Crystal data

C₁₆H₁₄ClNO
M _r = 271.73
Monoclinic,
a = 9.215 (4) Å
b = 9.210 (4) Å
c = 17.090 (8) Å
β = 102.842 (6)°
V = 1414.2 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.93, T _max = 0.94
11395 measured reflections
3172 independent reflections
1666 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.158
S = 1.06
3172 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706432X/is2254sup1.cif

e-64-0o206-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706432X/is2254Isup2.hkl

e-64-0o206-Isup2.hkl^{(155.7KB, hkl)}

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

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

Cg1 is the mid-point of atoms C15 and C16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.53	3.405 (4)	157
C6—H6⋯Cg1ⁱⁱ	0.93	3.02	3.75 (2)	136

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the mid-point of atoms C15 and C16.

Acknowledgments

The authors thank the National Science Foundation of Anhui Province (project No. 2004kj164zd), the Education Department of Anhui Province Program (grant Nos. 2006K J006TD and TD200707) and the National Science Foundation of China (project No. 20572001) for financial support of this work.

supplementary crystallographic information

Comment

Many active molecules in nature contain highly functionalized heterocyclic rings (Fairlamb, 2004). In recent research, we report a novel palladium catalyzed Heck intermolecular reactions of aryl halides with the nitron-containing olefins (Hu et al., 2003). We found that polyene amide was prepared by two steps (Riggi et al., 1992). The substrate of N-benzyl-N-(4-chlorophenyl)acrylamide is used to obtain this pyrrole skeleton (Park & Hoffmann, 1990; Otero & Cantero, 1995).

In this paper, we report the crystal structure of the title compound, C₁₆H₁₄ClNO (Fig. 1). The crystal data show that all bond lengths and angles in the title compound have normal values. The bond length of C15=C16 is 1.288 (4) Å, belonging to typical C_sp2—C_sp2 double bonds. The molecule contains two six-membered rings, A (C1—C6) and B (C8—C13). Rings A and B are not coplanar, the dihedral angle between ring A and ring B being 49.79 (11)°. In the structure there are a weak intermolecular C—H···O interaction [C2—H2···O1ⁱ, symmetry code: (i) -x, -y, 1 - z] and a C—H···π interaction [C6—H6···Cg1ⁱⁱ, Cg1 is the centroid of atoms C15 and C16; symmetry code: (ii) -x,1 - y,1 - z]. These weak intermolecular interactions extended the title compound molecules into a one-dimensional chain structure (Fig. 2) along the b axis.

Experimental

The solution of 4-chlorobenzenamine (12.75 g, 0.1 mol) and triethylamine (14 ml, 0.1 mol) in CCl₄ (20 ml) was placed in a three-necked flask equipped with reflux condenser, dropping funnel and mechanical stirrer. The 1-chloromethylbenzene (13.91 g, 0.11 mol) in CCl₄ (20 ml) was added at a rate such as to produce gentle reflux at room temperature. The crude product was recrystallized from C₂H₅OH; yield (21.54 g, 90%). N-benzyl-4-chlorobenzenamine (10.89 g, 0.05 mol) was stirred at ice-water in the presence of 2-propenoyl chloride (4.9 ml, 0.06 mol) and triethylamine (8.4 ml, 0.06 mol) in CCl4 (20 ml). The mixture was washed with water and the organic layer was dried by MgSO₄. The crude product was purified by flash column chromatography on silica gel (light petroleum/EtOAc, 8:1) to obtain the product (8.23 g, 61%). Colorless crystals of the N-benzyl-3-(4-chlorophenyl)-3-phenyl-propanamide suitable for X-ray diffraction were obtained from an ethyl acetate solution over one week.