N-[2-(1,3-Benzodioxol-5-yl)eth­yl]-2-chloro­acetamide

Hui-Chao Dong

doi:10.1107/S1600536808014232

. 2008 May 21;64(Pt 6):o1118. doi: 10.1107/S1600536808014232

N-[2-(1,3-Benzodioxol-5-yl)ethyl]-2-chloroacetamide

Hui-Chao Dong ^a,^*

PMCID: PMC2961617 PMID: 21202629

Abstract

The title compound, C₁₁H₁₂ClNO₃, crystallizes with two independent molecules in the asymmetric unit. Intermolecular N—H⋯O hydrogen bonds link the molecules related by translation along the b axis into two independent hydrogen-bonded chains. The crystal studied exhibited inversion twinning.

Related literature

For the crystal structures of related compounds, see: Kuehne et al. (1988 ▶). For details of the aplication of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-chloro-acetamide, see: Bernhard & Snieckus (1971 ▶); Ma et al. (2006 ▶). For bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₁H₁₂ClNO₃
M _r = 241.67
Orthorhombic,
a = 14.429 (3) Å
b = 5.1258 (10) Å
c = 30.679 (6) Å
V = 2269.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 (2) K
0.20 × 0.12 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.937, T _max = 0.971
15836 measured reflections
3949 independent reflections
2946 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.110
S = 1.13
3949 reflections
290 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ▶), 1304 Friedel pairs
Flack parameter: 0.47 (8)

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014232/cv2412sup1.cif

e-64-o1118-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014232/cv2412Isup2.hkl

e-64-o1118-Isup2.hkl^{(193.6KB, 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
N1—H1A⋯O3ⁱ	0.86	2.18	2.894 (4)	140
N2—H2B⋯O6ⁱⁱ	0.86	2.18	2.894 (4)	140

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

supplementary crystallographic information

Comment

The title compound (I) is an important intermediate for the synthesis of3, 4-dihydroisoquinoline and some other heterocyclic compounds (Bernhard & Snieckus, 1971; Ma et al., 2006). In this paper, we report its crystal structure.

Compound (I) crystallizes with two independent molecules in the non-centrosymmetric unit cell (Fig. 1). All bond lengths and angles in (I) are normal (Allen et al., 1987) and in a good agreement with those reported previously (Kuehne et al., 1988). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along b axis into two independent hydrogen-bonded chains.

Experimental

2-Benzo[1,3]dioxol-5-yl-ethylamine (20 mmol) was dissolved in CH₂Cl₂, and K₂CO₃ (30 mmol) was added, then chloroacetyl chloride (20 mmol) was added during 30 min at 273 K. After 2 h standing at room temperature, the solution was washed with water, the organic layer was separated, dried with Na₂SO₄ and evaporated to obtain the primary product. The pure product was isolated by recrystallization from ethyl acetate (1.50 g, 68%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.