2-Fluoro-N-o-tolyl­benzamide

Aamer Saeed; Rasheed Ahmad Khera; Shahid Ameen; Jim Simpson; Roderick G Stanley

doi:10.1107/S1600536808043122

. 2008 Dec 24;65(Pt 1):o201. doi: 10.1107/S1600536808043122

2-Fluoro-N-o-tolylbenzamide

Aamer Saeed ^a,^*, Rasheed Ahmad Khera ^a, Shahid Ameen ^a, Jim Simpson ^b, Roderick G Stanley ^b

PMCID: PMC2968107 PMID: 21581656

Abstract

In the title compound, C₁₄H₁₂FNO, the ortho-F atom and corresponding H atom on the fluorobenzene ring are disordered over two positions with occupancies of 0.856 (4) and 0.144 (4). The amide unit is planar with a maximum deviation of 0.0057 (16) Å and the amide plane makes dihedral angles of 38.27 (11)° with the fluorobenzene ring plane and 37.53 (10)° with the tolyl ring. The two benzene rings are inclined at an angle of 4.17 (15)°. In the crystal structure, chains form along b through N—H⋯O hydrogen bonds augmented by C—H⋯π interactions. Additional intermolecular C—H⋯O and C—H⋯F hydrogen bonds further stabilize the structure, forming layers in the ac plane.

Related literature

For related structures, see: Chopra & Guru Row (2008 ▶); Donnelly et al. (2008 ▶); Hou et al. (2004 ▶); Saeed et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₂FNO
M _r = 229.25
Monoclinic,
a = 10.749 (4) Å
b = 4.8245 (17) Å
c = 21.580 (7) Å
β = 93.820 (19)°
V = 1116.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 93 (2) K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T _min = 0.779, T _max = 0.995
7896 measured reflections
1228 independent reflections
925 reflections with I > 2σ(I)
R _int = 0.067
θ_max = 21.3°

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.06
1228 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker 2006 ▶); cell refinement: APEX2 and SAINT (Bruker 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808043122/hb2882sup1.cif

e-65-0o201-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043122/hb2882Isup2.hkl

e-65-0o201-Isup2.hkl^{(60.7KB, 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—HN1⋯O1ⁱ	0.85 (3)	2.08 (3)	2.887 (3)	158 (2)
C6—H6⋯F1′ⁱⁱ	0.95	2.60	3.219 (11)	123
C12—H12⋯O1ⁱⁱⁱ	0.95	2.63	3.434 (3)	143
C12—H12⋯F1′ⁱⁱⁱ	0.95	2.40	3.287 (11)	154
C14—H14C⋯Cg1ⁱ	0.98	2.98	3.702 (3)	131

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C8–C13 benzene ring.

Acknowledgments

We thank the University of Otago for purchase of the diffractometer.

supplementary crystallographic information

Comment

As part of our ongoing work on the structure of benzanilides and related compounds (Saeed et al., 2008), we report here the structure of the title 2-fluorobenzamide derivative, (I), Fig 1. The C2—C1—O1—N1—C8 unit is almost planar with a maximum deviation of 0.0057 (16)Å for N1. This plane makes dihedral angles of 38.27 (11) ° with the fluorobenzene ring plane and 37.53 (10)° with the tolyl ring. The two benzene rings are inclined at an angle of 4.17 (15)° giving the molecule a stepped structure. Bond distances in the molecule are not unusual (Allen et al., 1987) and agree well with those reported previously (see for example Chopra & Guru Row, 2008; Donnelly et al., 2008; Hou et al., 2004, Saeed et al., 2008).

In the crystal structure, chains form along b through N—H···O hydrogen bonds augmented by C—H···π interactions involving the methyl group and the tolyl rings (Table 1, Fig. 2). Additional intermolecular C—H···O and C—H···F hydrogen bonds further stabilize the structure forming layers in the ac plane, that stack down the b axis (Fig. 3).

Experimental

2-Fluorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-methylaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with 1 M aqueous HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue from CHCl₃ afforded (I) as colourless needles in an81% yield: Anal. calcd. for C₁₄H₁₂FNO: C 73.35, H 5.28, N 6.11%; found: C 73.30, H 5.32, N 6.09%