N-Benzyl-2-(2-chloro-5-methyl­phen­oxy)acetamide

Zhu-Bo Li; Xiao-Yan He; Yong-Sheng Xie; Guang-Cheng Qin

doi:10.1107/S1600536808038555

. 2008 Nov 22;64(Pt 12):o2426. doi: 10.1107/S1600536808038555

N-Benzyl-2-(2-chloro-5-methylphenoxy)acetamide

Zhu-Bo Li ^a,^*, Xiao-Yan He ^a, Yong-Sheng Xie ^b, Guang-Cheng Qin ^a

PMCID: PMC2959909 PMID: 21581394

Abstract

The asymmetric unit of the title compound, C₁₆H₁₆ClNO₂, contains two crystallographically independent molecules, which differ mainly in the orientation of the benzyl group with respect to the rest of the molecule. In the crystal packing, centrosymmetrically related molecules are linked into dimers via intermolecular C—H⋯O hydrogen-bond interactions.

Related literature

For a related structure, see: Li et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₆ClNO₂
M _r = 289.75
Triclinic,
a = 9.5549 (18) Å
b = 11.086 (2) Å
c = 14.725 (3) Å
α = 71.747 (4)°
β = 89.062 (4)°
γ = 85.655 (4)°
V = 1477.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.970, T _max = 0.985
7851 measured reflections
5194 independent reflections
2351 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.153
S = 0.98
5194 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038555/rz2267sup1.cif

e-64-o2426-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038555/rz2267Isup2.hkl

e-64-o2426-Isup2.hkl^{(254.3KB, 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
C3—H3⋯O4ⁱ	0.93	2.51	3.423 (4)	169
C19—H19⋯O2ⁱ	0.93	2.37	3.287 (4)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

This study was supported by the Key Program Projects of the Municipal Natural Science Foundation of Chongqing, China (grant No. CSTC, 2008 A A1001).

supplementary crystallographic information

Comment

As part of our continuing project on the study of the interactions occurring between small molecules and proteins (Li et al.; 2008), we report here the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules which differ mainly in the orientation of the benzyl groups (C10—C15 and C26—C32) bound to the amidic N atoms with respect of the mean plane through the rest of the molecule (dihedral angles of 87.03 (8) and 68.74 (6)° respectively). The O1—C8—C9—O2 and O3—C24—C25—O4 torsion angles are -176.5 (3) and -179.0 (3)°, respectively. These values can be compared with that of 10.5 (3)° found in the similar dichloro compound (Li et al.; 2008). In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C—H···O hydrogen bonds (Table 1), forming fourteen-membered rings of graph set motif R²₂(14) (Bernstein et al., 1995).

Experimental

A solution of 2-chloro-5-methylphenol (1.0 mmol), N-benzyl-2-chloroacetamide (1.1 mmol), K₂CO₃ (1.1 mmol) and CH₃CN (20 ml) was refluxed for 3 h. After completion of the reaction (by TLC monitoring), the solution was cooled and the solvent was evaporated under reduced pressure. The residue was poured into water and adjusted to pH 6–7 with dilute hydrochloric acid (10%) and extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO₄. The mixture was then filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl acetate as eluent (yield 86%). Crystals suitable for X-ray diffraction were obtained by slow evaparation of an ethyl acetate/hexane (1:1 v/v) solution at room temperature for 10 days.