Literature DB >> 21202368

N-Benzyl-2-hydroxy-benzamide.

Qiu-Xia Zhang1, Bi-Song Zhang.   

Abstract

In the title compound, C(14)H(13)NO(2), the mean planes through the benzyl and 2-hydoxybenzamide units make a dihedral angle of 68.81 (7)°. There is an intra-molecular O-H⋯O hydrogen bond involving the carbonyl O atom and the 2-hydr-oxy substituent. In the crystal structure, N-H⋯O hydrogen bonds link symmetry-related mol-ecules 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.

Entities:  

Year:  2008        PMID： 21202368      PMCID： PMC2961206          DOI： 10.1107/S1600536808010453

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C14H13NO2 M = 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 Δρmax = 0.17 e Å−3 Δρmin = −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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010453/su2048sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010453/su2048Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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
Rigaku R-AXIS RAPID diffractometer2665 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 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
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.
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)*
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)
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)
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)
Table 1

Hydrogen-bond geometry (Å, °)

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 code: (i) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
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1.  N-Benzyl-2,3,4,5,6-penta-fluoro-benz-amide.

Authors:  Arto Valkonen; Tanja Lahtinen; Kari Rissanen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-31
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