2-(4-Bromo­phen­yl)-N-(5-methyl­pyridin-2-yl)acetamide

Hoong-Kun Fun; Chin Wei Ooi; Prakash S Nayak; B Narayana; B K Sarojini

doi:10.1107/S1600536812032631

. 2012 Jul 25;68(Pt 8):o2526. doi: 10.1107/S1600536812032631

2-(4-Bromophenyl)-N-(5-methylpyridin-2-yl)acetamide

Hoong-Kun Fun ^a,^*,^‡, Chin Wei Ooi ^a, Prakash S Nayak ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3414974 PMID: 22904961

Abstract

The asymmetric unit of the title compound, C₁₄H₁₃BrN₂O, consists of two molecules; the dihedral angles between the pyridine and benzene rings are 87.99 (9) and 84.28 (9)°. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring in each molecule. In the crystal, molecules are linked via N—H⋯N and C—H⋯O hydrogen bonds into a three-dimensional network. The crystal structure also features weak π–π stacking interactrions between the benzene rings [centroid-to-centroid distance = 3.6829 (12) Å].

Related literature

For related structures, see: Fun et al. (2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₄H₁₃BrN₂O
M _r = 305.17
Monoclinic,
a = 14.0086 (16) Å
b = 9.4215 (11) Å
c = 20.610 (2) Å
β = 109.040 (2)°
V = 2571.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 3.19 mm⁻¹
T = 100 K
0.35 × 0.31 × 0.16 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.404, T _max = 0.626
28356 measured reflections
7539 independent reflections
5774 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.068
S = 1.03
7539 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.84 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/S1600536812032631/hb6903sup1.cif

e-68-o2526-sup1.cif^{(33KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032631/hb6903Isup2.hkl

e-68-o2526-Isup2.hkl^{(368.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032631/hb6903Isup3.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
N2A—H1N2⋯N1B ⁱ	0.84	2.28	3.114 (2)	175
N2B—H2N2⋯N1A ⁱⁱ	0.82	2.21	3.035 (2)	176
C3A—H3AA⋯O1B ⁱⁱⁱ	0.95	2.58	3.208 (2)	124
C4A—H4AA⋯O1A	0.95	2.22	2.832 (3)	121
C10A—H10A⋯O1A ^iv	0.95	2.49	3.422 (3)	169
C4B—H4BA⋯O1B	0.95	2.25	2.846 (3)	120

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

Acknowledgments

HKF and CWO thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. BN thanks 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., 2012a), we report herein the crystal structure of the title compound (I).

The asymmetric unit of the title compound (I) consists of two crystallographically independent molecules (A and B) as shown in Fig. 1. In both molecules, the pyridine (N1A/C1A–C5A and N1B/C1B–C5B) rings are essentially planar with maximum deviations of 0.013 (2) Å at N1A atom and 0.004 (2) Å at C2B and C5B atoms. The dihedral angle between the pyridine ring and bromo-substituted benzene ring (C8–C13) is 87.99 (9) in molecule A and 84.28 (9)° in molecule B. An intramolecular C—H···O interaction (Table 1), generates an S(6) ring motif (Bernstein et al., 1995) in each molecule. The bond lengths and angles are comparable to those in a related structure (Fun et al., 2012b).

In the crystal (Fig. 2), the molecules are linked via N2A—H1N2···N1B, N2B—H2N2···N1A, C3A—H3AA···O1B and C10A—H10A···O1A hydrogen bonds (Table 1) into a three-dimensional network. The crystal structure also features weak π—π interactions between bromo-substituted benzene rings (C8A–C13A and C8B–C13B) [centroid–centroid distance = 3.6829 (12) Å; x, 3/2 - y, -1/2 + z].

Experimental

4-Bromophenylacetic acid (0.213 g, 1 mmol), 2-amino-5-methylpyridine (0.108 g, 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 which was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Colourless blocks were grown from dichloromethane solution by the slow evaporation method (m.p. 459–461 K).