2-Bromo-N-(4-chloro­phen­yl)-2-methyl­propanamide

Rodolfo Moreno-Fuquen; David E Quintero; Fabio Zuluaga; Alan R Kennedy; Regina H De Almeida Santos

doi:10.1107/S1600536811035562

. 2011 Sep 14;67(Pt 10):o2580. doi: 10.1107/S1600536811035562

2-Bromo-N-(4-chlorophenyl)-2-methylpropanamide

Rodolfo Moreno-Fuquen ^a,^*, David E Quintero ^a, Fabio Zuluaga ^a, Alan R Kennedy ^b, Regina H De Almeida Santos ^c

PMCID: PMC3201238 PMID: 22064690

Abstract

In the title molecule, C₁₀H₁₁BrClNO, there is a twist between the mean plane of the amide group and the benzene ring [C(=O)—N—C—C torsion angle = −27.1 (3)°]. In the crystal, intermolecular N—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into chains along [010].

Related literature

For initiators in ATRP processes (polymerization by atom transfer radical), see: Matyjaszewski & Xia (2001 ▶); Pietrasik & Tsarevsky (2010 ▶). For end-functionalized linear polymers, see: Matyjaszewski & Mueller (2008 ▶); Stenzel-Rosenbaum et al. 2001 ▶). For hydrogen-bond graph-set motifs, see: Etter (1990 ▶). For hydrogen bonding, see: Nardelli (1995 ▶).

Experimental

Crystal data

C₁₀H₁₁BrClNO
M _r = 276.56
Orthorhombic,
a = 9.7449 (3) Å
b = 10.1063 (3) Å
c = 22.8803 (7) Å
V = 2253.36 (12) Å³
Z = 8
Mo Kα radiation
μ = 3.85 mm⁻¹
T = 123 K
0.45 × 0.22 × 0.08 mm

Data collection

Oxford Diffraction Gemini S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.387, T _max = 1.000
9676 measured reflections
2684 independent reflections
2225 reflections with I > 2σ(I)
R _int = 0.028
Standard reflections: 0

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.069
S = 1.05
2684 reflections
133 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035562/hg5088sup1.cif

e-67-o2580-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035562/hg5088Isup2.hkl

e-67-o2580-Isup2.hkl^{(129.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035562/hg5088Isup3.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
N1—H1N⋯O1ⁱ	0.81 (3)	2.17 (3)	2.972 (2)	169 (3)
C10—H10⋯O1ⁱ	0.95	2.71	3.433 (3)	133
C4—H4B⋯O1ⁱ	0.98	2.53	3.453 (3)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database (Allen, 2002 ▶). RMF and FZ also thank the Universidad del Valle, Colombia, and Instituto de Química de São Carlos, USP, Brazil for partial financial support.

supplementary crystallographic information

Comment

The title compound (I), is a monofunctional alkyl halyde derivative, which can be used as an initiator in Atom Transfer Radical Polymerization processes (ATRP) (Matyjaszewski & Xia, 2001; Pietrasik & Tsarevsky, 2010). This derivative can form end-functionalized linear polymers when used as an initiator (Matyjaszewski et al. 2008; Stenzel-Rosenbaum et al. 2001). The molecular structure of (I) is shown in Fig. 1. There is a twist between the mean plane of the amide group and benzene ring giving a C3—N1—C5—C6 torsion angle of -27.1 (3)°. The crystal structure is stabilized by intermolecular N—H···O and weak C—H···O hydrogen bonds (see Table 1, Nardelli, 1995). Indeed, molecules of (I) are linked by N1—H1N···O1ⁱ, C10—H10···O1ⁱ and C4—H4B···O1ⁱ hydrogen bonds (i: -x + 3/2,+y + 1/2,+z) which lead to the formation of C(4) (Etter, 1990) one dimensional chain along [010] (Fig. 2).

Experimental

The initial reagents were purchased from Aldrich Chemical Co. and were used as received. In a 100 mL round bottom flask 4-chloroaniline (2.315 mmoles, 0.295 g), triethylamine (0.463 mmol, 0.027 g) were mixed, then a solution of 2-bromo isobutyryl bromide (0.450 g) in anhydrous THF (5 ml) was added drop wise, under an argon stream. The reaction was carried out in a dry bag overnight under magnetic stirring. The solid was filtered off and dichloromethane (20 ml) added to the organic phase which was washed with brine (50 ml) followed by water (10 ml). The solution was concentrated at low pressure affording colourless crystals and recrystalized from a solution of hexane and ethyl acetate (80:20). M.p. 386 (1) K.