3-Bromo-N-(3,5-di-tert-butyl­phen­yl)propanamide

Anwar Abo-Amer; Mahmoud Al-Refai; Richard J Puddephatt; Basem F Ali

doi:10.1107/S1600536814012094

. 2014 Jun 14;70(Pt 7):o770. doi: 10.1107/S1600536814012094

3-Bromo-N-(3,5-di-tert-butylphenyl)propanamide

Anwar Abo-Amer ^a, Mahmoud Al-Refai ^a, Richard J Puddephatt ^b, Basem F Ali ^a,^*

PMCID: PMC4120558 PMID: 25161559

Abstract

The title compound, C₁₇H₂₆BrNO, exhibits a small twist between the amide residue and the benzene ring [C—N—C—C torsion angle = 29.4 (5)°]. In the crystal, the amido NH group is involved in N—H⋯O hydrogen bonding, which connects molecules into chains parallel to the c axis.

Related literature

For the related structure of a derivative with an alkyl-N-aryl substituent, see: Palakshamurthy et al. (2014 ▶), with an alkyl-N-phenylsulfonyl substituent, see: Shakuntala et al. (2011 ▶) and with a chloro-N-phenyl substituent, see: Betz et al. (2011 ▶). For details of the synthesis, see: Bentiss & Lagrenée (1999 ▶); Hill et al. (2007 ▶). graphic file with name e-70-0o770-scheme1.jpg

Experimental

Crystal data

C₁₇H₂₆BrNO
M _r = 340.30
Monoclinic,
a = 15.666 (2) Å
b = 11.4885 (16) Å
c = 9.7829 (14) Å
β = 97.436 (4)°
V = 1745.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.35 mm⁻¹
T = 150 K
0.40 × 0.20 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.455, T _max = 0.789
21557 measured reflections
4005 independent reflections
2738 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.145
S = 1.04
4005 reflections
187 parameters
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker, 2014 ▶); software used to prepare material for publication: local programs.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814012094/nk2223sup1.cif

e-70-0o770-sup1.cif^{(652.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012094/nk2223Isup2.hkl

e-70-0o770-Isup2.hkl^{(219.8KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814012094/nk2223Isup3.cml

CCDC reference: 1005148

Additional supporting information: 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—H1C⋯O1ⁱ	0.88	2.01	2.889 (3)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank Dr Aneta Borecki and Dr Paul Boyle (University of Western Ontario) for their help in data collection and refinement.

supplementary crystallographic information

S1. Comment

The title compound C₁₇H₂₅BrNO, is a brominated derivative of a secondary amide bearing a di-tert-butylbenzene ring. It exhibits a small twist between the amide residue and benzene ring [the C3—N1—C4—C5 torsion angle = 29.5 (4)°]. The N—H and C=O bonds are anti to each other (Fig. 1), as observed in many other derivatives (Shakuntala et al., 2011). In the structure, bond distances and angles are within normal range (Table 1) and comparable to reported values in amide derivatives (Palakshamurthy et al., 2014, Betz et al., 2011). The torsion angle of C3—N1—C4—C9 and C3—N1—C4—C5 are -153.2 (3)° and 29.5 (4)°, respectively. The amido NH group is involved in N—H···O [2.01 Å] hydrogen bonding, which connects molecules into chains parallel to c axis (Fig. 2).

S2. Experimental

Synthesis of (2,5-Bis(2-pyridyl)-1,3,4-oxadiazole)dimethylplatinum(II), [PtMe₂(ox)]

A mixture of [Pt₂Me₄(µ-SMe₂)₂] (50 mg, 0.087 mmol)) (Hill et al., 2007) and ox (ox = 2,5-bis(2-pyridyl)-1,3,4-oxadiazole) (38 mg, 0.170Dr mmol) (Bentiss and Lagrenée, 1999) in dry ether (10 ml) was stirred for 1 h. A red precipitate resulted. The precipitate was isolated and washed with acetone (3 × 5 ml). The product was recrystallized from CH₂Cl₂. A yellow solid was produced and dried in vacuo.

The title compound was crystallized unintentionally from the reaction mixture of the complex (2,5-Bis(2-pyridyl)-1,3,4-oxadiazole)dimethylplatinum(II), [PtMe₂(ox)] (0.05 g, 0.112 mmol) and, the commercially available N-(3,5-di-tert-butylphenyl)-3-bromopropanamide (0.052 g, 0.129 mmol) in acetone (15 ml) was stirred for 5 h at room temperature. The reaction color changed to yellow suspension. The solvent was evaporated under vacuum and the resulting solid was washed with water (2 × 10 ml) and pentane (3 × 10 ml). The isolated yellow solid is highly soluble in CH₂Cl₂ solvent, which was dried under high vacuum. Yield 87%. A suitable crystal for X-ray diffraction analysis was selected for data collection.