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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1108.
Published online 2009 April 25. doi:  10.1107/S1600536809013014
PMCID: PMC2977786

N-(2-Amino­phen­yl)-2-anilinobenzamide

Abstract

In the title compound, C19H17N3O, the planes of the aromatic substituents attached to the benzamide moiety are almost perpendicular to one another, making a dihedral angle of 88.16 (7)°. The observed conformation of the mol­ecule is produced by an intra­molecular N—H(...)O hydrogen bond.

Related literature

For the synthesis, see: Martín et al. (2006 [triangle]); Charton et al. (2006 [triangle]). For related structures, see: Yusof et al. (2003 [triangle]); Du et al. (2009 [triangle]).

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Object name is e-65-o1108-scheme1.jpg

Experimental

Crystal data

  • C19H17N3O
  • M r = 303.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1108-efi1.jpg
  • a = 6.707 (3) Å
  • b = 25.95 (1) Å
  • c = 9.480 (5) Å
  • β = 103.398 (7)°
  • V = 1605.0 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 93 K
  • 0.40 × 0.27 × 0.10 mm

Data collection

  • Rigaku Spider diffractometer
  • Absorption correction: none
  • 6515 measured reflections
  • 1844 independent reflections
  • 1695 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.072
  • S = 1.00
  • 1844 reflections
  • 224 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013014/im2107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013014/im2107Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

supplementary crystallographic information

Comment

Nowadays many researchers are intrested in the synthesis of new insecticides. Benzamide or its derivatives or analogs are used in the pharmaceutical industry for this purpose. We herein report the crystal structure of the title compound.

Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges. The planes of the aromatic substituents attached to the benzamide moiety (C7—C12 and C14—C19) are almost perpendicular to one another, with a dihedral angle of 88.16 (7)° whereas the dihedral angle between C7—C12 and C1—C6 measures to 47.28 (9)°. The planes between C7—C12 and the amide moiety C12/C13/N2/O1 enclose an angle of 63.06 (8)°.

Experimental

The title compound was prepared according to the reported procedure of Martín et al. (2006). and Charton et al. (2006). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane.

Refinement

H atoms were placed in calculated positions with N—H = 0.88–0.93 Å and C—H = 0.95 Å and refined using a riding model with Uiso(H) = 1.2Ueq(C,N). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C19H17N3OF(000) = 640
Mr = 303.36Dx = 1.255 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2858 reflections
a = 6.707 (3) Åθ = 3.1–27.5°
b = 25.95 (1) ŵ = 0.08 mm1
c = 9.480 (5) ÅT = 93 K
β = 103.398 (7)°Platelet, colorless
V = 1605.0 (14) Å30.40 × 0.27 × 0.10 mm
Z = 4

Data collection

Rigaku Spider diffractometer1695 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.029
graphiteθmax = 27.5°, θmin = 3.1°
ω scansh = −8→8
6515 measured reflectionsk = −33→31
1844 independent reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3
1844 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 0.14 e Å3
2 restraintsΔρmin = −0.15 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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)

xyzUiso*/Ueq
O10.4009 (2)0.47225 (5)0.56166 (13)0.0295 (3)
N20.3896 (2)0.51617 (6)0.35407 (16)0.0257 (3)
N10.4426 (3)0.36962 (7)0.52152 (19)0.0368 (4)
N30.0087 (3)0.53595 (9)0.16236 (19)0.0418 (5)
H3A0.106 (4)0.5228 (9)0.121 (3)0.053 (7)*
H3B−0.103 (4)0.5495 (10)0.097 (3)0.063 (8)*
C10.3021 (4)0.28921 (8)0.3998 (2)0.0435 (6)
H10.36470.29550.32120.052*
C20.1803 (4)0.24613 (9)0.3980 (3)0.0600 (7)
H20.16050.22300.31830.072*
C30.0878 (5)0.23638 (10)0.5100 (4)0.0725 (9)
H30.00280.20700.50800.087*
C40.1209 (5)0.27031 (10)0.6262 (4)0.0674 (8)
H40.05880.26380.70490.081*
C50.2422 (4)0.31325 (9)0.6295 (3)0.0470 (6)
H50.26330.33600.71000.056*
C60.3335 (3)0.32336 (8)0.5156 (2)0.0366 (5)
C70.5729 (3)0.38514 (8)0.4348 (2)0.0326 (5)
C80.7016 (3)0.34982 (9)0.3887 (2)0.0425 (5)
H80.69540.31440.41270.051*
C90.8377 (4)0.36594 (10)0.3087 (2)0.0475 (6)
H90.92310.34130.27730.057*
C100.8519 (3)0.41732 (10)0.2733 (2)0.0429 (6)
H100.94670.42810.21870.052*
C110.7264 (3)0.45261 (9)0.3184 (2)0.0331 (5)
H110.73660.48800.29520.040*
C120.5841 (3)0.43752 (8)0.39754 (18)0.0271 (4)
C130.4524 (3)0.47661 (7)0.44460 (18)0.0245 (4)
C140.2603 (3)0.55640 (7)0.38352 (19)0.0272 (4)
C150.3209 (3)0.58570 (8)0.5089 (2)0.0324 (4)
H150.45050.57970.57280.039*
C160.1931 (4)0.62359 (9)0.5410 (2)0.0420 (5)
H160.23410.64350.62690.050*
C170.0059 (4)0.63226 (10)0.4473 (2)0.0492 (6)
H17−0.08310.65790.46970.059*
C18−0.0532 (4)0.60405 (10)0.3216 (2)0.0468 (6)
H18−0.18210.61080.25770.056*
C190.0727 (3)0.56574 (8)0.2863 (2)0.0339 (5)
H1N0.400 (4)0.3966 (10)0.563 (3)0.053 (7)*
H2N0.414 (3)0.5148 (7)0.269 (2)0.030 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0355 (7)0.0417 (8)0.0137 (6)−0.0010 (6)0.0106 (5)−0.0004 (5)
N20.0232 (8)0.0413 (9)0.0144 (7)0.0023 (7)0.0076 (6)0.0006 (7)
N10.0459 (11)0.0375 (10)0.0305 (9)−0.0001 (8)0.0162 (8)−0.0020 (8)
N30.0251 (9)0.0777 (15)0.0209 (9)0.0039 (9)0.0022 (8)−0.0025 (9)
C10.0528 (14)0.0313 (11)0.0418 (13)0.0092 (10)0.0019 (11)0.0049 (10)
C20.0694 (18)0.0288 (12)0.0729 (18)0.0060 (11)−0.0017 (16)0.0033 (12)
C30.078 (2)0.0320 (14)0.107 (3)−0.0012 (13)0.0214 (19)0.0199 (16)
C40.084 (2)0.0450 (15)0.081 (2)0.0042 (14)0.0353 (17)0.0261 (15)
C50.0580 (15)0.0393 (12)0.0475 (14)0.0108 (11)0.0199 (12)0.0167 (11)
C60.0423 (13)0.0324 (11)0.0330 (11)0.0081 (9)0.0043 (9)0.0101 (9)
C70.0315 (11)0.0456 (13)0.0207 (10)0.0045 (9)0.0058 (8)−0.0018 (9)
C80.0457 (13)0.0486 (13)0.0325 (12)0.0126 (10)0.0076 (10)−0.0025 (10)
C90.0411 (13)0.0673 (17)0.0364 (13)0.0193 (12)0.0137 (11)−0.0061 (11)
C100.0275 (11)0.0734 (17)0.0294 (12)0.0091 (10)0.0098 (9)−0.0053 (11)
C110.0226 (9)0.0560 (13)0.0207 (10)0.0036 (9)0.0050 (8)−0.0017 (9)
C120.0239 (9)0.0413 (11)0.0151 (9)0.0032 (8)0.0025 (7)−0.0017 (8)
C130.0198 (9)0.0383 (11)0.0153 (9)−0.0034 (8)0.0037 (7)−0.0020 (8)
C140.0263 (10)0.0371 (10)0.0193 (9)0.0006 (8)0.0079 (8)0.0041 (8)
C150.0366 (11)0.0403 (11)0.0211 (10)−0.0017 (9)0.0082 (8)0.0019 (9)
C160.0592 (15)0.0385 (12)0.0340 (11)0.0015 (10)0.0225 (11)0.0003 (10)
C170.0615 (16)0.0546 (15)0.0392 (14)0.0227 (12)0.0274 (13)0.0120 (11)
C180.0390 (13)0.0721 (16)0.0319 (12)0.0204 (12)0.0132 (10)0.0145 (11)
C190.0287 (11)0.0548 (13)0.0196 (9)0.0035 (9)0.0085 (8)0.0064 (9)

Geometric parameters (Å, °)

O1—C131.241 (2)C7—C81.397 (3)
N2—C131.342 (2)C7—C121.411 (3)
N2—C141.425 (2)C8—C91.380 (3)
N2—H2N0.86 (2)C8—H80.9500
N1—C71.391 (3)C9—C101.384 (4)
N1—C61.400 (3)C9—H90.9500
N1—H1N0.88 (3)C10—C111.377 (3)
N3—C191.389 (3)C10—H100.9500
N3—H3A0.90 (3)C11—C121.400 (3)
N3—H3B0.93 (3)C11—H110.9500
C1—C21.382 (4)C12—C131.480 (2)
C1—C61.389 (3)C14—C151.390 (3)
C1—H10.9500C14—C191.398 (3)
C2—C31.372 (4)C15—C161.384 (3)
C2—H20.9500C15—H150.9500
C3—C41.387 (4)C16—C171.378 (3)
C3—H30.9500C16—H160.9500
C4—C51.376 (4)C17—C181.376 (4)
C4—H40.9500C17—H170.9500
C5—C61.383 (3)C18—C191.394 (3)
C5—H50.9500C18—H180.9500
C13—N2—C14123.37 (15)C8—C9—C10121.1 (2)
C13—N2—H2N118.0 (13)C8—C9—H9119.4
C14—N2—H2N118.0 (13)C10—C9—H9119.4
C7—N1—C6128.24 (19)C11—C10—C9119.0 (2)
C7—N1—H1N110.2 (17)C11—C10—H10120.5
C6—N1—H1N118.5 (17)C9—C10—H10120.5
C19—N3—H3A117.9 (16)C10—C11—C12121.5 (2)
C19—N3—H3B113.5 (16)C10—C11—H11119.3
H3A—N3—H3B114 (2)C12—C11—H11119.3
C2—C1—C6120.4 (2)C11—C12—C7119.10 (18)
C2—C1—H1119.8C11—C12—C13119.91 (18)
C6—C1—H1119.8C7—C12—C13120.96 (17)
C3—C2—C1120.8 (3)O1—C13—N2122.03 (17)
C3—C2—H2119.6O1—C13—C12121.07 (17)
C1—C2—H2119.6N2—C13—C12116.89 (15)
C2—C3—C4118.7 (3)C15—C14—C19120.58 (18)
C2—C3—H3120.7C15—C14—N2119.84 (17)
C4—C3—H3120.7C19—C14—N2119.57 (17)
C5—C4—C3121.1 (3)C16—C15—C14120.2 (2)
C5—C4—H4119.4C16—C15—H15119.9
C3—C4—H4119.4C14—C15—H15119.9
C4—C5—C6120.1 (3)C17—C16—C15119.5 (2)
C4—C5—H5119.9C17—C16—H16120.2
C6—C5—H5119.9C15—C16—H16120.2
C5—C6—C1118.9 (2)C18—C17—C16120.5 (2)
C5—C6—N1116.9 (2)C18—C17—H17119.8
C1—C6—N1124.09 (19)C16—C17—H17119.8
N1—C7—C8120.88 (19)C17—C18—C19121.2 (2)
N1—C7—C12120.29 (18)C17—C18—H18119.4
C8—C7—C12118.77 (19)C19—C18—H18119.4
C9—C8—C7120.6 (2)N3—C19—C18120.96 (19)
C9—C8—H8119.7N3—C19—C14121.04 (19)
C7—C8—H8119.7C18—C19—C14117.92 (19)
C6—C1—C2—C30.2 (4)N1—C7—C12—C13−2.4 (3)
C1—C2—C3—C4−0.8 (4)C8—C7—C12—C13−179.51 (17)
C2—C3—C4—C50.6 (4)C14—N2—C13—O10.2 (3)
C3—C4—C5—C60.1 (4)C14—N2—C13—C12179.19 (17)
C4—C5—C6—C1−0.7 (4)C11—C12—C13—O1−145.63 (18)
C4—C5—C6—N1175.5 (2)C7—C12—C13—O132.5 (3)
C2—C1—C6—C50.5 (3)C11—C12—C13—N235.3 (2)
C2—C1—C6—N1−175.4 (2)C7—C12—C13—N2−146.50 (18)
C7—N1—C6—C5169.1 (2)C13—N2—C14—C1557.6 (2)
C7—N1—C6—C1−14.9 (3)C13—N2—C14—C19−121.91 (19)
C6—N1—C7—C8−37.1 (3)C19—C14—C15—C161.8 (3)
C6—N1—C7—C12145.9 (2)N2—C14—C15—C16−177.67 (18)
N1—C7—C8—C9−176.8 (2)C14—C15—C16—C17−0.4 (3)
C12—C7—C8—C90.2 (3)C15—C16—C17—C18−0.9 (3)
C7—C8—C9—C100.7 (3)C16—C17—C18—C190.7 (3)
C8—C9—C10—C11−0.5 (3)C17—C18—C19—N3177.3 (2)
C9—C10—C11—C12−0.7 (3)C17—C18—C19—C140.7 (3)
C10—C11—C12—C71.6 (3)C15—C14—C19—N3−178.58 (18)
C10—C11—C12—C13179.76 (18)N2—C14—C19—N30.9 (3)
N1—C7—C12—C11175.75 (17)C15—C14—C19—C18−2.0 (3)
C8—C7—C12—C11−1.3 (3)N2—C14—C19—C18177.54 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.88 (3)1.96 (3)2.714 (3)142 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2107).

References

  • Charton, J., Mizzi, S. G., Fontaine, M. A. D., Foufelle, F., Hainault, I., Espiard, J. G. B., Caignard, D. H. & Sergheraert, C. (2006). Bioorg. Med. Chem.14, 4490–4518. [PubMed]
  • Du, P., Jiang, X. K. & Li, Z. T. (2009). Tetrahedron Lett.50, 316–319.
  • Martín, A., Mesa, M., Docampo, M. L., Gómez, V. & Pellón, R. F. (2006). Synth. Commun.36, 271–277.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yusof, M. S. M., Yamin, B. M. & Shamsuddin, M. (2003). Acta Cryst. E59, o810–o811.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography