2-(4-Bromo­phen­yl)-N-(2,6-dimethyl­phen­yl)acetamide

Hoong-Kun Fun; Ching Kheng Quah; Prakash S Nayak; B Narayana; B K Sarojini

doi:10.1107/S1600536812034617

. 2012 Aug 11;68(Pt 9):o2678. doi: 10.1107/S1600536812034617

2-(4-Bromophenyl)-N-(2,6-dimethylphenyl)acetamide

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Prakash S Nayak ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3435700 PMID: 22969571

Abstract

In the title compound, C₁₆H₁₆BrNO, the dihedral angle between the benzene rings is 69.8 (2)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [100]. Adjacent molecules in the chains are also linked by C—H⋯O interactions which, along with the N—H⋯O hydrogen bonds, generate R ₂ ¹(6) loops.

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₆BrNO
M _r = 318.21
Monoclinic,
a = 4.7146 (6) Å
b = 22.999 (3) Å
c = 13.5350 (15) Å
β = 91.138 (3)°
V = 1467.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.79 mm⁻¹
T = 296 K
0.18 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.635, T _max = 0.822
14048 measured reflections
3352 independent reflections
1593 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.143
S = 1.01
3352 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034617/hb6926sup1.cif

e-68-o2678-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034617/hb6926Isup2.hkl

e-68-o2678-Isup2.hkl^{(164.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034617/hb6926Isup3.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—H1N1⋯O1ⁱ	0.91 (4)	1.95 (4)	2.847 (4)	166 (3)
C7—H7B⋯O1ⁱ	0.97	2.38	3.240 (5)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the two benzene rings (C1-C6 and C9-C14) make a dihedral angle of 69.8 (2)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a, 2011b, 2012a, 2012b).

In the crystal structure, Fig. 2, molecules are linked via N1–H1N1···O1 and C7–H7B···O1 hydrogen bonds (Table 1) into one-dimensional [100] chains which contain R₂¹ (6) ring motifs (Bernstein et al., 1995).

Experimental

4-Bromophenylacetic acid (0.213 g, 1 mmol), 2,6-Dimethylaniline (0.1 ml, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring. The resulting solution was extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Colourless plates were grown from a methanol and N,N-dimethylformamide (1:1) solvent mixture by the slow evaporation method (m.p.:479-481 K).