N-(4-Cyano­phen­yl)-2,6-difluoro­benzamide

Hoong-Kun Fun; Jia Hao Goh; Janardhana Gowda; A M Khader; B Kalluraya

doi:10.1107/S1600536810046507

. 2010 Nov 17;66(Pt 12):o3192. doi: 10.1107/S1600536810046507

N-(4-Cyanophenyl)-2,6-difluorobenzamide

Hoong-Kun Fun ^a,^*,^‡, Jia Hao Goh ^a,^§, Janardhana Gowda ^b, A M Khader ^b, B Kalluraya ^b

PMCID: PMC3011460 PMID: 21589486

Abstract

In the title compound, C₁₄H₈F₂N₂O, the amide plane is inclined at dihedral angles of 28.12 (12) and 32.89 (12)° with respect to the two benzene rings; the dihedral angle between the two rings is 5.58 (5)°. In the crystal, intermolecular N—H⋯O and C—H⋯F hydrogen bonds link adjacent molecules into a double-chain structure along the b axis.

Related literature

For general background to and applications of the title compound, see: Ashwood et al. (1990 ▶); Kees et al. (1989 ▶); Ragavan et al. (2010 ▶); Carmellino et al. (1994 ▶); Rauko et al. (2001 ▶). For a closely related benzamide structure, see: Cronin et al. (2000 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₄H₈F₂N₂O
M _r = 258.22
Monoclinic,
a = 9.3377 (11) Å
b = 5.0793 (6) Å
c = 24.500 (3) Å
β = 100.202 (3)°
V = 1143.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.27 × 0.14 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.968, T _max = 0.984
27219 measured reflections
4135 independent reflections
3176 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.03
4135 reflections
204 parameters
All H-atom parameters refined
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.23 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 datablocks global, I. DOI: 10.1107/S1600536810046507/is2630sup1.cif

e-66-o3192-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046507/is2630Isup2.hkl

e-66-o3192-Isup2.hkl^{(202.7KB, 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
N1—H1N1⋯O1ⁱ	0.863 (15)	2.107 (15)	2.9029 (12)	153.3 (14)
C12—H12⋯F1ⁱⁱ	0.940 (16)	2.473 (16)	3.4066 (14)	172.4 (13)

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

A number of benzamide derivatives were reported as anti-hypertensive (Ashwood et al., 1990), anti-diabetic (Kees et al., 1989), anti-bacterial (Ragavan et al., 2010), anti-fungal (Carmellino et al., 1994) and anti-cancer (Rauko et al., 2001) activities. On the basis of these considerations, our particular attention was paid for the synthesis of some benzamide derivatives.

In the title benzamide derivative, the amino moiety (C7/N1/O1) is essentially planar, as indicated by the C7–O1–N1–H1N1 torsion angle of -1.4 (18)°. The mean plane through the amido moiety is inclined at dihedral angles of 32.89 (12) and 28.12 (12)°, respectively, with the C1–C6 and C8–C13 benzene rings. The dihedral angle between the two benzene rings being 5.58 (5)°. All bond lengths and angles are comparable to values observed in a closely related benzamide structure (Cronin et al., 2000). In the crystal packing, adjacent molecules are interconnected into two-molecule-wide infinite chains propagating along the [010] direction (Fig. 2) via intermolecular N1—H1N1···O1 and C12—H12···F1 hydrogen bonds (Table 1).

Experimental

A mixture of 4-amino benzonitrile (4.2 mmol), 2,6-difluorobenzoic acid (4.6 mmol) and triethyl amine (21 mmol) was dissolved in methylene dichloride (5 ml). The resulting solution was cooled to 273 K followed by the drop wise addition of 50 % phosphoric acid cyclic anhydride solution in ethyl acetate (4 ml, 6.3 mmol) and stirred for 12 h. The completion of reaction was checked by TLC. Evaporation of solvent gave 2,6-difluoro-N-(p-cyanophenyl)benzamide as solid mass, which was then stirred with saturated NaHCO₃ solution to remove excess of acid. Single crystals suitable for X-ray analysis were obtained by crystallization from acetone under slow evaporation. M.p. 418 K.