N-Benzyl-2-hydroxy­benzamide

Qiu-Xia Zhang; Bi-Song Zhang

doi:10.1107/S1600536808010453

. 2008 Apr 23;64(Pt 5):o884. doi: 10.1107/S1600536808010453

N-Benzyl-2-hydroxybenzamide

Qiu-Xia Zhang ^a,^*, Bi-Song Zhang ^a

PMCID: PMC2961206 PMID: 21202368

Abstract

In the title compound, C₁₄H₁₃NO₂, the mean planes through the benzyl and 2-hydoxybenzamide units make a dihedral angle of 68.81 (7)°. There is an intramolecular O—H⋯O hydrogen bond involving the carbonyl O atom and the 2-hydroxy substituent. In the crystal structure, N—H⋯O hydrogen bonds link symmetry-related molecules into one-dimensional chains extending along the a-axis direction. These chains are further connected via C—H⋯O hydrogen bonds, forming a sheet-like structure

Related literature

For related literature, see: Agwade (1982 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₂
M _r = 227.25
Monoclinic,
a = 12.478 (3) Å
b = 8.3503 (17) Å
c = 12.664 (3) Å
β = 118.02 (3)°
V = 1164.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 (2) K
0.33 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.977, T _max = 0.983
11112 measured reflections
2665 independent reflections
1648 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.116
S = 1.03
2665 reflections
207 parameters
All H-atom parameters refined
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010453/su2048sup1.cif

e-64-0o884-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010453/su2048Isup2.hkl

e-64-0o884-Isup2.hkl^{(130KB, 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	0.882 (18)	2.083 (18)	2.9191 (18)	158.1 (18)
O1—HO1⋯O2	0.98 (3)	1.56 (3)	2.4886 (19)	157 (2)
C2—H2⋯O1ⁱ	0.956 (19)	2.58 (2)	3.507 (2)	162.5 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the financial support of the Education Office of Zhejiang Province (grant No. 20051316).

supplementary crystallographic information

Comment

Over a quater of a century ago (Agwade, 1982) published a thesis on Potential Central Nervous System Active Agents, which included the synthesis of aromatic N-benzyl amides. One of the compounds synthesized was N-benzyl-2-hydroxy-benzamide, (I), whose crystal structure has not been descibed until now.

The molecular structure of compound I is illustrated in Fig. 1. The bond lengths and angles are close to normal values (Allen et al., 1987). There is an intramolecular O-H···O hydrogen bond in the molecule involving the carbonyl O-atom and the 2-hydroxyl substituent (Table 1). The best planes through the benzyl (atoms C8,C9-C14) and the 2-hydoxybenzamide (atoms C1-C6,C7,N1,O1,O2) moieties are inclined to one another by 68.81 (7)°.

In the crystal structure of I symmetry related molecules are connected via an N-H···O hydrogen bond to form chains running along the a direction. These chains are further connected connected via C-H···O hydrogen bonds (Table 1) to form a sheet-like structure (Fig 2).

Experimental

Freshly prepared CuCO₃ (0.310 g 2.50 mmol), [C₆H₄(COOC₆H₄CONHCH₂ph)₂](0.350 g 0.601 mmol), 2-chloro-benzoic acid (0.160 g 1.022 mmol), and 15 ml CH₃OH/H₂O (1:2,v/v) were mixed and stirred for ca. 1.5 h. The resulting suspension was heated in a 23 ml Teflon-lined stainless steel autoclave at 373 K for 7 days. After the autoclave was cooled to room temperature, and colorless block-like crystals, suitable for X-ray analysis, were obtained.