(2-Amino­phen­yl)(p-tol­yl)methanone

Dun-Lin Zhang; Shan Liu; Xiao-Li Zhang

doi:10.1107/S1600536810049147

. 2010 Nov 30;66(Pt 12):o3359. doi: 10.1107/S1600536810049147

(2-Aminophenyl)(p-tolyl)methanone

Dun-Lin Zhang ^a,^*, Shan Liu ^b, Xiao-Li Zhang ^b

PMCID: PMC3011377 PMID: 21589628

Abstract

In the title compound, C₁₄H₁₃NO, the two six-membered rings make a dihedral angle of 52.8 (3)°. An intramolecular N—H⋯O hydrogen bond involving an amine H atom and the adjacent carbonyl O atom occurs. In the crystal, N—H⋯O and C—H⋯N intermolecular hydrogen bonds are observed, which may be effective in stabilizing the structure.

Related literature

For the uses of 5-nitrothiophene-2-carboxylic acid, see: Shetty et al. (1999 ▶). For the synthesis of the title compound, see: Zhu et al. (2005 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₃NO
M _r = 211.25
Orthorhombic,
a = 7.7720 (16) Å
b = 10.490 (2) Å
c = 14.114 (3) Å
V = 1150.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.977, T _max = 0.992
2387 measured reflections
1241 independent reflections
984 reflections with I > 2σ(I)
R _int = 0.023
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.114
S = 1.01
1241 reflections
154 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049147/su2231sup1.cif

e-66-o3359-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049147/su2231Isup2.hkl

e-66-o3359-Isup2.hkl^{(61.4KB, 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—H0A⋯O1	0.87 (3)	2.08 (3)	2.723 (4)	131 (3)
N1—H0B⋯O1ⁱ	0.82 (3)	2.45 (3)	3.220 (4)	158 (3)
C11—H11A⋯O1ⁱ	0.93	2.53	3.319 (4)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

(2-Aminophenyl)(p-tolyl)methanone and its derivitives are important monomers, being utilized to synthesize oligomers containing a quinoline unit (Shetty et al., 1999). We report herein on the crystal structure of the title compound, (2-Aminophenyl)(p-tolyl)methanone.

In the title molecule (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. An amine H-atom and the adjacent carbonyl O-atom forms an intramolecular N-H···O hydrogen bond (Fig. 1, Table 1). The two aromatic rings are planar, with a dihedral angle of 52.8 (3)°.

In the crystal, N-H···O and C—H···N intermolecular hydrogen bonds are observed, which stabilize the crystal structure (Fig. 2, Table 1).

Experimental

(2-Aminophenyl)(p-tolyl)methanone was prepared by the method reported in the literature (Zhu et al., 2005). Single crystals were obtained by dissolving (2-aminophenyl)(p-tolyl)methanone (0.5 g, 2.37 mmol) in ethyl acetate (50 ml) and evaporating the solvent slowly at room temperature for about 10 d.