N-(4,4′-Dibromo-[1,1′-biphen­yl]-2-yl)benzamide

J Josephine Novina; G Vasuki; Abhishek Baheti; K R Justin Thomas

doi:10.1107/S1600536813000597

. 2013 Jan 12;69(Pt 2):o222. doi: 10.1107/S1600536813000597

N-(4,4′-Dibromo-[1,1′-biphenyl]-2-yl)benzamide

J Josephine Novina ^a, G Vasuki ^b,^*, Abhishek Baheti ^c, K R Justin Thomas ^c

PMCID: PMC3569757 PMID: 23424503

Abstract

In the title compound, C₁₉H₁₃Br₂NO, the dihedral angle between the rings of the biphenyl group is 53.59 (14)°. The ring of the benzamide group is inclined to the phenyl rings of the biphenyl group by 23.87 (15) and 75.89 (15)°. There are no significant intermolecular interactions in the crystal structure.

Related literature

For applications of the title compound, see: Libman & Slack (1951 ▶); Mandadapu et al. (2009 ▶); Youn & Bihn (2009 ▶); Yulan et al. (2010 ▶). For pharmacological properties of biphenyl aniline, see: Zhu et al. (2008 ▶). For related structures, see: Li & Cui (2011 ▶); Kuś et al. (2009 ▶); Hammond et al. (2009 ▶); Gowda et al. (2010 ▶); Novina et al. (2012 ▶).

Experimental

Crystal data

C₁₉H₁₃Br₂NO
M _r = 431.12
Monoclinic,
a = 9.0188 (5) Å
b = 11.6415 (9) Å
c = 16.0068 (12) Å
β = 100.737 (2)°
V = 1651.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 4.91 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.238, T _max = 0.374
16420 measured reflections
3453 independent reflections
2302 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.075
S = 1.01
3453 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(24.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000597/su2551sup1.cif

e-69-0o222-sup1.cif^{(24.7KB, cif)}

Click here for additional data file.^{(169.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000597/su2551Isup2.hkl

e-69-0o222-Isup2.hkl^{(169.4KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000597/su2551Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Sophisticated Analytical Instrument Facility, IIT Madras, Chennai, for the data collection.

supplementary crystallographic information

Comment

Biphenyl aniline, a subclass of biaryl compounds, has been recognized as a privileged structure in drug discovery. Its derivatives have been pursued as anti–phlogistic, analgesic, anti–obesity, and anti–tumor agents (Zhu et al., 2008). Amide substituted biphenyl derivatives are commonly used to develop antiparasitic agents for the treatment of African sleeping sickness disease (Libman & Slack, 1951; Mandadapu et al., 2009; Youn & Bihn, 2009; Yulan et al., 2010). Benzamides are recognized as one of the important bioactive skeletons and exhibit various potent pharmaceutical activities. As part of our studies on the substituent effects on the structures and other aspects of dibromo biphenyl derivatives, 4,4'-Dibromo-2-nitrobiphenyl (Novina et al., 2012), in the present work we report herein on the synthesis and crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the two benzene rings of the biphenyl group are twisted with respect to each other by 53.59 (14)°, which is similar to to the arrangement [53.52 (14)°] found in 2,5-Bis(bromomethyl)biphenyl (Kuś et al., 2009), but is somewhat larger than the angle of 45.5 (2)° found in 3,3',5,5'-Tetranitrobiphenyl (Hammond et al., 2009). The amide unit C1—N1—C13(O1)—C14 is planar [r.m.s deviation = 0.013 Å], and subtends dihedral angles of 12.38 (12)° and 32.34 (11)° respectively to the C1-C6 and C14-C19 phenyl rings. These two aromatic rings are inclined to one another by 23.87 (15)°, while rings C7-C12 and C14-C19 are inclined to one another by 75.89 (15)°. The C13═O1 and C13—N1 bond distances are 1.221 (3) and 1.360 (3) Å, respectively, showing the electron delocalization in the amide fragment. The N—H and C═O bonds in the amide group are anti to each other, similar to that observed in 2-Chloro-N-(2,3-dimethylphenyl)-benzamide (Gowda et al., 2010), and N-(3,5-Dimethoxyphenyl)benzamide (Li & Cui, 2011). The length of the bond connecting the phenyl rings, 1.489 (4) Å, is close to the standard value of 1.48 Å for a Csp²—Csp² single bond.

In the crystal, there are no significant interactions and the structure is stabilized by Van der Waals interactions (Fig. 2).

Experimental

To a dry THF solution of 4,4'-dibromo-[1,1'-biphenyl]-2-amine (3.27 g, 10 mmol) and triethylamine (3 ml) was added drop wise a dry THF solution (40 ml) of benzoyl chloride at 273 K. After stirring at room temperature for 20 h, the solution was poured into water (80 ml) and extracted with dichloromethane (2 × 50 ml). The combined organic extracts were dried over anhydrous Na₂SO₄ and evaporated to dryness. This gave white solid which was further recrystallized with dichloromethane-hexanes [Yield 3.0 g (70%); M.p. 443–445 K]. HRMS calcd. for C₁₉H₁₃Br₂NO [M]⁺ m/z 428.9364 found 428.9363. Spectroscopic data for the title compound is available in the archived CIF.