2-Methyl-N-(3-methylphenyl)benzamide

Abstract

In the structure of the title compound (N3MP2MBA), C15H15NO, the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N3MP2MBA are similar to those in 2-methyl-N-phenyl­benzamide, N-(3,4-dimethyl­phen­yl)benzamide and other benzanilides. The amide group, –NHCO–, makes a dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. N—H⋯O hydrogen bonds give rise to infinite chains running along the b axis of the crystal structure.

2-Methyl-N-(4-methylphenyl)benzamide

“…The N-H and C=O bonds in the amide group of (I) are trans to each other ( Fig. 1), similar to what is observed in N-(4-methylphenyl)benzamide (N4MPBA) (Gowda et al, 2008c), 2-methyl-N-(phenyl)-benzamide (NP2MBA) (Gowda et al, 2008a), and 2methyl-N-(3-methylphenyl)-benzamide (N3MP2MBA) (Gowda et al, 2008b). Further, the conformation of the amide oxygen in (I) is syn to the ortho-methyl group in the benzoyl ring, similar to what is observed in NP2MBA and N3MP2MBA (Gowda et al, 2008a, b).…”

N-(3-Chlorophenyl)-2-methylbenzamide

“…1) is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring and the conformations of the N-H and C=O bonds are anti to each other, identical to that observed in 2-methyl-N-(3-methylphenyl)-benzamide (N3MP2MBA). The bond parameters in N3CP2MBA are similar to those in 2-methyl-N-(phenyl)-benzamide (Gowda et al, 2008a), N3MP2MBA (Gowda et al, 2008b) and other benzanilides (Gowda et al, 2003). The amide group, -NHCOmakes a dihedral angle of 55.8 (7)° with the benzoyl ring, while that between benzoyl and aniline rings is 37.5 1 (Table 1) is given in Fig.…”

“…Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97. In the present work, the structure of 2-methyl-N-(3-chlorophenyl)-benzamide (N3CP2MBA) has been determined as part of substituent effect studies on the solid state structures of benzanilides (Gowda et al, 2003;Gowda et al (2008aGowda et al ( , 2008b. The conformation of the N-H bond in N3CP2MBA (Fig.…”

2-Methyl-N-o-tolylbenzamide

“…These are inclined at 4.94 (7)° to one another giving the overall molecule a stepped structure. The ortho-methyl groups of the two tolyl rings are anti to one another in contrast to the situation for the isomeric 2-methyl-N-(3-methylphenyl)benzamide structure where the methyl substituents are mutually syn (Gowda et al, 2008b). Bond distances within the molecule are normal and similar to those observed in comparable structures (Gowda et al, 2008a(Gowda et al, ,b,c 2009.…”

“…For background to our work on benzamide derivatives, see: Saeed et al (2008). For the 2-methyl-N-(3-methylphenyl)benzamide isomer, see: Gowda et al (2008b). For other related structures see: Gowda et al (2008aGowda et al ( ,c, 2009.…”