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Acta Cryst. (2008). E64, o884    [ doi:10.1107/S1600536808010453 ]

N-Benzyl-2-hydroxybenzamide

Q.-X. Zhang and B.-S. Zhang

Abstract top

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

Comment top

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).

Related literature top

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

Experimental top

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.

Refinement top

All of the H atoms were located in difference Fourier syntheses and were freely refined: O-H = 0.98 (3), N-H = 0.882 (18), and C-H = 0.94 (2) - 1.010 (16) Å.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the moleculecular structure of I, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. The crystal packing diagram for compound I, viewed down the b axis. Dashed lines indicate N-H···O hydrogen bonds.
N-Benzyl-2-hydroxybenzamide top
Crystal data top
C14H13NO2F000 = 480
Mr = 227.25Dx = 1.296 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6913 reflections
a = 12.478 (3) Åθ = 3.0–27.5º
b = 8.3503 (17) ŵ = 0.09 mm−1
c = 12.664 (3) ÅT = 290 (2) K
β = 118.02 (3)ºBlock, colorless
V = 1164.9 (6) Å30.33 × 0.22 × 0.20 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2665 independent reflections
Radiation source: fine-focus sealed tube1648 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
Detector resolution: 10 pixels mm-1θmax = 27.5º
T = 290(2) Kθmin = 3.0º
ω scansh = −15→16
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −10→10
Tmin = 0.977, Tmax = 0.983l = −16→16
11112 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.043  w = 1/[σ2(Fo2) + (0.0564P)2 + 0.0491P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.17 e Å−3
2665 reflectionsΔρmin = −0.14 e Å−3
207 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (2)
Secondary atom site location: difference Fourier map
Crystal data top
C14H13NO2V = 1164.9 (6) Å3
Mr = 227.25Z = 4
Monoclinic, P21/nMo Kα
a = 12.478 (3) ŵ = 0.09 mm−1
b = 8.3503 (17) ÅT = 290 (2) K
c = 12.664 (3) Å0.33 × 0.22 × 0.20 mm
β = 118.02 (3)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2665 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1648 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.983Rint = 0.037
11112 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043207 parameters
wR(F2) = 0.116All H-atom parameters refined
S = 1.03Δρmax = 0.17 e Å−3
2665 reflectionsΔρmin = −0.14 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.29704 (10)0.74227 (17)−0.23736 (9)0.0731 (4)
O20.49480 (9)0.60089 (14)−0.16419 (9)0.0600 (4)
N10.64585 (9)0.63326 (15)0.02206 (11)0.0449 (4)
C10.45255 (11)0.76116 (16)−0.03318 (11)0.0396 (4)
C20.48553 (14)0.82179 (19)0.07995 (14)0.0493 (5)
C30.40715 (15)0.9140 (2)0.10230 (16)0.0592 (6)
C40.29300 (15)0.9477 (2)0.01061 (17)0.0604 (6)
C50.25762 (14)0.8909 (2)−0.10172 (16)0.0576 (6)
C60.33637 (12)0.79771 (18)−0.12499 (13)0.0478 (5)
C70.53270 (11)0.66022 (17)−0.06264 (12)0.0412 (4)
C80.73259 (14)0.5375 (2)0.00128 (16)0.0508 (5)
C90.80422 (12)0.63678 (17)−0.04347 (14)0.0460 (5)
C100.92320 (15)0.6768 (3)0.03099 (19)0.0722 (7)
C110.98716 (18)0.7699 (3)−0.0108 (2)0.0875 (9)
C120.9333 (2)0.8228 (3)−0.1254 (2)0.0785 (9)
C130.81540 (19)0.7850 (3)−0.20000 (19)0.0721 (8)
C140.75139 (16)0.6917 (2)−0.15893 (16)0.0596 (6)
HN10.6728 (14)0.6819 (19)0.0917 (16)0.059 (5)*
H20.5651 (15)0.7995 (18)0.1431 (15)0.060 (5)*
HO10.367 (2)0.681 (3)−0.230 (2)0.106 (7)*
H30.4331 (15)0.952 (2)0.1817 (17)0.078 (5)*
H40.2386 (15)1.009 (2)0.0252 (15)0.071 (5)*
H50.1770 (17)0.913 (2)−0.1697 (16)0.081 (5)*
H8A0.6833 (14)0.455 (2)−0.0610 (14)0.062 (5)*
H8B0.7896 (14)0.4913 (19)0.0805 (15)0.062 (5)*
H100.9607 (17)0.633 (2)0.1088 (19)0.087 (6)*
H111.070 (2)0.793 (3)0.042 (2)0.107 (7)*
H120.9743 (19)0.887 (3)−0.1597 (18)0.099 (7)*
H130.7716 (18)0.825 (3)−0.283 (2)0.098 (7)*
H140.6696 (16)0.668 (2)−0.2122 (15)0.070 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0512 (6)0.1059 (10)0.0395 (6)0.0150 (7)0.0024 (5)−0.0056 (6)
O20.0503 (6)0.0798 (8)0.0421 (6)0.0005 (5)0.0152 (5)−0.0147 (5)
N10.0376 (6)0.0549 (8)0.0399 (7)0.0001 (5)0.0162 (5)0.0025 (6)
C10.0369 (6)0.0420 (8)0.0378 (7)−0.0052 (6)0.0159 (5)0.0030 (6)
C20.0465 (8)0.0557 (10)0.0433 (8)−0.0040 (7)0.0190 (7)−0.0014 (7)
C30.0664 (10)0.0594 (10)0.0604 (11)−0.0070 (8)0.0370 (9)−0.0106 (8)
C40.0586 (10)0.0493 (10)0.0853 (13)0.0013 (8)0.0438 (9)0.0000 (9)
C50.0440 (8)0.0553 (10)0.0696 (11)0.0052 (7)0.0235 (8)0.0109 (8)
C60.0408 (7)0.0533 (9)0.0436 (8)−0.0018 (7)0.0150 (6)0.0048 (7)
C70.0379 (7)0.0458 (8)0.0374 (8)−0.0052 (6)0.0156 (5)0.0021 (6)
C80.0454 (8)0.0501 (9)0.0583 (10)0.0065 (7)0.0256 (7)0.0099 (8)
C90.0447 (7)0.0410 (8)0.0558 (9)0.0018 (6)0.0266 (6)−0.0020 (7)
C100.0477 (9)0.0840 (14)0.0753 (13)−0.0025 (9)0.0209 (8)0.0173 (11)
C110.0510 (11)0.0993 (17)0.1074 (18)−0.0151 (11)0.0333 (11)0.0117 (13)
C120.0808 (13)0.0764 (14)0.1031 (17)−0.0141 (11)0.0639 (13)−0.0013 (12)
C130.0835 (13)0.0814 (14)0.0652 (12)−0.0113 (10)0.0464 (10)0.0005 (10)
C140.0579 (10)0.0695 (11)0.0538 (10)−0.0107 (8)0.0283 (8)−0.0039 (8)
Geometric parameters (Å, °) top
O1—C61.3506 (18)C10—C111.385 (3)
O2—C71.2456 (17)C11—C121.355 (3)
O1—HO10.98 (3)C12—C131.360 (4)
N1—C71.3311 (19)C13—C141.381 (3)
N1—C81.466 (2)C2—H20.956 (19)
N1—HN10.882 (18)C3—H30.954 (19)
C1—C71.483 (2)C4—H40.94 (2)
C1—C61.401 (2)C5—H50.99 (2)
C1—C21.387 (2)C8—H8A1.010 (16)
C2—C31.375 (3)C8—H8B0.995 (17)
C3—C41.379 (3)C10—H100.94 (2)
C4—C51.361 (3)C11—H110.95 (3)
C5—C61.389 (3)C12—H120.97 (3)
C8—C91.511 (3)C13—H130.99 (2)
C9—C141.370 (2)C14—H140.94 (2)
C9—C101.375 (3)
O1···O22.4886 (19)C9···H4iv3.034 (17)
O1···N1i2.9191 (18)C14···H4iv2.989 (17)
O2···C143.260 (3)HN1···C22.554 (19)
O2···O12.4886 (19)HN1···H22.00 (3)
O1···H2i2.58 (2)HN1···O1iii2.083 (18)
O1···HN1i2.083 (18)H2···N12.597 (18)
O2···HO11.56 (3)H2···HN12.00 (3)
O2···H8A2.416 (18)H2···O1iii2.58 (2)
O2···H142.59 (2)HO1···O21.56 (3)
O2···H5ii2.692 (19)HO1···C72.16 (2)
N1···O1iii2.9191 (18)HO1···H5ii2.50 (3)
N1···H22.597 (18)H4···C9iv3.034 (17)
C1···C3iv3.554 (2)H4···C14iv2.989 (17)
C1···C8v3.549 (2)H5···O2vi2.692 (19)
C3···C1iv3.554 (2)H5···HO1vi2.50 (3)
C6···C8v3.507 (2)H8A···O22.416 (18)
C7···C7v3.400 (2)H8A···H142.56 (2)
C7···C143.483 (3)H8A···H13vii2.54 (3)
C8···C1v3.549 (2)H8A···C1v3.075 (18)
C8···C6v3.507 (2)H8A···C2v3.060 (18)
C14···C73.483 (3)H8B···H102.32 (3)
C14···O23.260 (3)H8B···C6v3.073 (17)
C1···H8Av3.075 (18)H10···H8B2.32 (3)
C2···H8Av3.060 (18)H13···H8Aviii2.54 (3)
C2···HN12.554 (19)H14···O22.59 (2)
C6···H8Bv3.073 (17)H14···C73.09 (2)
C7···H143.09 (2)H14···H8A2.56 (2)
C7···HO12.16 (2)
C6—O1—HO1102.3 (13)C9—C14—C13121.17 (19)
C7—N1—C8122.74 (13)C1—C2—H2118.7 (11)
C7—N1—HN1119.3 (12)C3—C2—H2119.8 (11)
C8—N1—HN1117.7 (13)C2—C3—H3118.8 (12)
C6—C1—C7118.17 (12)C4—C3—H3121.6 (12)
C2—C1—C6117.83 (15)C3—C4—H4120.2 (11)
C2—C1—C7124.00 (14)C5—C4—H4119.2 (11)
C1—C2—C3121.50 (16)C4—C5—H5122.9 (12)
C2—C3—C4119.62 (17)C6—C5—H5116.9 (12)
C3—C4—C5120.55 (19)N1—C8—H8A106.4 (11)
C4—C5—C6120.15 (17)N1—C8—H8B105.6 (11)
C1—C6—C5120.35 (14)C9—C8—H8A109.4 (10)
O1—C6—C1121.46 (15)C9—C8—H8B108.8 (11)
O1—C6—C5118.19 (15)H8A—C8—H8B114.1 (13)
O2—C7—C1120.79 (13)C9—C10—H10117.9 (14)
O2—C7—N1120.61 (14)C11—C10—H10121.6 (14)
N1—C7—C1118.60 (12)C10—C11—H11118.5 (15)
N1—C8—C9112.64 (13)C12—C11—H11121.0 (15)
C8—C9—C10120.97 (16)C11—C12—H12123.9 (13)
C8—C9—C14120.74 (16)C13—C12—H12116.2 (13)
C10—C9—C14118.28 (18)C12—C13—H13122.5 (15)
C9—C10—C11120.3 (2)C14—C13—H13117.6 (15)
C10—C11—C12120.5 (2)C9—C14—H14120.7 (11)
C11—C12—C13119.9 (2)C13—C14—H14118.2 (11)
C12—C13—C14119.8 (2)
C8—N1—C7—O21.6 (2)C2—C3—C4—C5−0.2 (3)
C8—N1—C7—C1−178.95 (14)C3—C4—C5—C60.2 (3)
C7—N1—C8—C989.06 (18)C4—C5—C6—O1179.22 (16)
C6—C1—C2—C30.4 (2)C4—C5—C6—C10.1 (2)
C7—C1—C2—C3−179.59 (16)N1—C8—C9—C10104.4 (2)
C2—C1—C6—O1−179.48 (15)N1—C8—C9—C14−74.4 (2)
C2—C1—C6—C5−0.4 (2)C8—C9—C10—C11−179.0 (2)
C7—C1—C6—O10.5 (2)C14—C9—C10—C11−0.2 (3)
C7—C1—C6—C5179.56 (15)C8—C9—C14—C13178.77 (18)
C2—C1—C7—O2175.27 (15)C10—C9—C14—C13−0.1 (3)
C2—C1—C7—N1−4.2 (2)C9—C10—C11—C120.1 (4)
C6—C1—C7—O2−4.7 (2)C10—C11—C12—C130.3 (4)
C6—C1—C7—N1175.80 (14)C11—C12—C13—C14−0.6 (4)
C1—C2—C3—C4−0.1 (3)C12—C13—C14—C90.5 (3)
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z−1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x+1, −y+2, −z; (v) −x+1, −y+1, −z; (vi) −x+1/2, y+1/2, −z−1/2; (vii) −x+3/2, y−1/2, −z−1/2; (viii) −x+3/2, y+1/2, −z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1iii0.882 (18)2.083 (18)2.9191 (18)158.1 (18)
O1—HO1···O20.98 (3)1.56 (3)2.4886 (19)157 (2)
C2—H2···O1iii0.956 (19)2.58 (2)3.507 (2)162.5 (15)
C14—H14···O20.94 (2)2.59 (2)3.260 (3)128.8 (14)
Symmetry codes: (iii) x+1/2, −y+3/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1i0.882 (18)2.083 (18)2.9191 (18)158.1 (18)
O1—HO1···O20.98 (3)1.56 (3)2.4886 (19)157 (2)
C2—H2···O1i0.956 (19)2.58 (2)3.507 (2)162.5 (15)
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2.
Acknowledgements top

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

references
References top

Agwade, V. C. (1982). Chem. Eng. Data, 27, 479–481.

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.