N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]-2-meth­oxy­benzamide

S Nanjunda Swamy; H R Manjunath; B S Priya; Basappa; M A Sridhar; K S Rangappa

doi:10.1107/S1600536810050269

. 2010 Dec 18;67(Pt 1):o198. doi: 10.1107/S1600536810050269

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methoxybenzamide

S Nanjunda Swamy ^a, H R Manjunath ^b, B S Priya ^c, Basappa ^c, M A Sridhar ^b, K S Rangappa ^c,^*

PMCID: PMC3050277 PMID: 21522699

Abstract

In the title compound, C₁₆H₁₁F₃N₂O₂, the carboxamide group connecting the two aromatic rings is in a syn-periplanar configuration; the molecule is non-planar; the dihedral angle between the two aromatic rings is 13.95 (18)°. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds.

Related literature

For nucleosome, a repeat unit of chromatin, see: Luger & Richmond (1998 ▶). For the biological activity of substituted amide derivatives, see: Bylov et al. (1999 ▶); Gududuru et al. (2004 ▶). For the preparation of the title compound, see: Mantelingu et al. (2007 ▶). For a related structure, see: Saeed et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₁F₃N₂O₂
M _r = 320.27
Monoclinic,
a = 15.117 (2) Å
b = 13.907 (2) Å
c = 14.5410 (11) Å
β = 107.360 (8)°
V = 2917.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.30 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer
3420 measured reflections
1985 independent reflections
1623 reflections with I > 2σ(I)
R _int = 0.016
θ_max = 23.3°

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.206
S = 1.03
1985 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976) ▶; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050269/jh2220sup1.cif

e-67-0o198-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050269/jh2220Isup2.hkl

e-67-0o198-Isup2.hkl^{(97.8KB, hkl)}

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
N7—H6⋯O15	0.96	1.90	2.648 (3)	133
C4—H12⋯O17ⁱ	0.96	2.41	3.346 (4)	165
C1—H15⋯O17	0.96	2.19	2.819 (4)	122

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the DST and the Government of India (project SP/I2/FOO/93) and the University of Mysore for financial assistance. HRM would like to thank the UGC–BRS and the University of Mysore for the award of a fellowship. SNS is grateful to the University Grants Commission (UGC), Government of India, for financial support under the major research project [grant No. 38–220/2009 (SR)]. SNS also expresses his sincere gratitude to J. S. S. Mahavidyapeetha for encouragement of this research work.

supplementary crystallographic information

Comment

Nucleosome, a repeat unit of chromatin is made up of an octameric histone core, bearing two copies of H2A, H2B, H3 and H4 with 145–147 bp DNA wrapped around the central domain (Luger & Richmond, 1998). Several chromatin modifiers are reponsible for adding different post-translational marks like acetylation, methylation, phosphorylation and others on N-terminal histone tails and for dictating the degree of genomic compaction. Histone acetyltransferases add the acetyl group on the specific lysine of histone H3 and H4 N-terminal, and these signatures increase the accessibility of the underlying chromatin at specific genes or over vast regions of the genome. Compounds comprising an amide bond as backbone have a wide range of biological activities. Among the natural and synthetic substituted amide derivatives, there are compounds possessing anti-proliferative (Gududuru et al. 2004), anti-viral, antimalarial, general anesthetics, anti-inflammatory (Bylov et al. 1999) and anti-microbial properties. In continuation of our research on benzamides, we have synthesized the title compound by the condenstation reaction and herein we report the single X-ray crystal structure of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methoxybemzamide.

A perspective view of the title compound is shown in Fig. 1. The carboxamide group connecting the two aromatic rings is in syn-periplanar-configuration. This is indicated by the torsion angle value of -7.6 (5)° about the atoms C6—N7—C8—O17. The two aromatic rings are out of plane with the dihedral angle value of 13.95 (18)° between the least squares planes of the rings. This value is very low when compare to the value of 57.69 (3)° (Saeed et al. 2010) reported earlier. This can be understood in terms of the different substituents on the phenyl ring. The CN triple bond is affected by the π-delocalization which is evident from the value 0.854 (6)Å for C22—N23. The methoxy group attached to one of the aromatic ring lies within the plane of the ring and can be oriented in trans conformation. This is confirmed by the torsion angle value of 179.1 (3)° about the atoms C9—C10—O15—C16. The geometry around the C8 atom of the keto group is distorted trigonal as indicated by the bond angles of 120.6 (3)°, 122.4 (3)° and 117.0 (2)° for the atoms C9—C8—O17, N7—C8—O17 and C9—C8—N7, respectively. The crystal structure is stabilized by intermolecular C—H···O and intramolecular N—H···O, C—H···F and C—H···O hydrogen bonds. The intermolecular hydrogen bond C4—H12···O17 has the bond length of 3.346 (4)Å and the bond angle of 165° with the symmetry code x,-y,-1/2 + z. The molecules exhibit layered stackings when viewd down the b axis as shown in Fig. 2.

Experimental

N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-methoxybenzamide was synthesized as per the procedure reported in the literature (Mantelingu et al. 2007) earlier. The final product was obtained by recrystallization using methonol as a solvent. Slow evaporation of the solvent yielded colorless crystals after five days.