PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1107.
Published online 2009 April 25. doi:  10.1107/S1600536809013026
PMCID: PMC2977785

2-Anilino-N-methyl-N-phenyl­benzamide

Abstract

The title compound, C20H18N2O, is composed of three aromatic rings, the dihedral angles between the phenyl and benzamide rings, and between the benzamide and aniline rings being 59.86 (9) and 46.57 (10)°, respectively. The mol­ecular structure is stabilized by an intra­molecular N—H(...)O hydrogen bond involving the amino H atom and the benzamide carbonyl O atom. In the crystal structure, C—H(...)O and C—H(...)π inter­actions are present.

Related literature

For the synthesis of the title compound, see: Martín et al. (2006 [triangle]); Charton et al. (2006 [triangle]). For related structures, see: Du et al. (2009 [triangle]); Qi et al. (2002 [triangle]). For further information on mol­ecular recognition and self-assembly, see: Brunsveld et al. (2001 [triangle]); Prins et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1107-scheme1.jpg

Experimental

Crystal data

  • C20H18N2O
  • M r = 302.36
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1107-efi1.jpg
  • a = 11.086 (2) Å
  • b = 18.150 (4) Å
  • c = 7.5962 (17) Å
  • V = 1528.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 93 K
  • 0.40 × 0.30 × 0.20 mm

Data collection

  • Rigaku Spider diffractometer
  • Absorption correction: none
  • 12048 measured reflections
  • 1887 independent reflections
  • 1803 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.080
  • S = 1.18
  • 1887 reflections
  • 213 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.18 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/S1600536809013026/su2103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013026/su2103Isup2.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

Aromatic amides have found extensive applications in preorganized rationally designed monomers for efficient molecular recognition and self-assembly (Brunsveld et al., 2001; Prins et al., 2001). Herein we report on the crystal structure of the title compound.

The bond lengths and angles in the title compound, illustrated in Fig. 1, are within normal ranges. The dihedral angles between plane (N1/C7/O1) and rings A (C1—C6), and B (C8—C13) are 56.30 (19) and 34.59 (19)°, respectively. Rings A and C (C14—C19) are inclined to one another by 14.0 (1)°, while the central ring, B, is inclined to rings A and C by 59.86 (9) and 46.57 (10)%, respectively.

The molecular structure is stabilized by an intramolecular N—H···O hydrogen bond, involving the amino (N2) H-atom and the benzamide carbonyl O-atom (O1) (Table 1). In the crystal structure symmetry related molecules are linked by a C-H···O interaction and there are also a number of C—H···π interactions present (Table 1).

Experimental

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

Refinement

In the final cycles of refinement, in the absence of significant anomalous scattering effects, 1609 Friedel pairs were merged and Δf'' set to zero. The amino H-atom was located in a difference Fourier map and freely refined [N-H = 0.85 (2) Å]. The C-bound H atoms were placed in calculated positions [C-H = 0.95 - 0.98 Å] and treated as riding atoms [Uiso(H) = 1.2 or 1.5Ueq(parent C-atom)]. Friedal pairs were merged [1609 refections (85%)].

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. The intramolecular N—H···O hydrogen bond is shown as a dashed line.

Crystal data

C20H18N2OF(000) = 640
Mr = 302.36Dx = 1.314 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5383 reflections
a = 11.086 (2) Åθ = 3.3–27.5°
b = 18.150 (4) ŵ = 0.08 mm1
c = 7.5962 (17) ÅT = 93 K
V = 1528.4 (6) Å3Block, colorless
Z = 40.40 × 0.30 × 0.20 mm

Data collection

Rigaku Spider diffractometer1803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 27.5°, θmin = 3.4°
ω scansh = −14→14
12048 measured reflectionsk = −23→20
1887 independent reflectionsl = −9→9

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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.18w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3
1887 reflections(Δ/σ)max = 0.029
213 parametersΔρmax = 0.37 e Å3
1 restraintΔρmin = −0.18 e Å3

Special details

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 > 2sigma(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
O10.31344 (11)0.23042 (7)0.31485 (19)0.0223 (4)
N10.17863 (14)0.22432 (8)0.5355 (2)0.0181 (4)
N20.39961 (14)0.36734 (8)0.2705 (2)0.0209 (5)
C10.15046 (16)0.31901 (10)0.7624 (3)0.0185 (5)
C20.08545 (17)0.34772 (10)0.9013 (3)0.0214 (5)
C3−0.02095 (17)0.31422 (11)0.9550 (3)0.0227 (5)
C4−0.06272 (17)0.25292 (10)0.8662 (3)0.0236 (5)
C50.00131 (18)0.22422 (10)0.7240 (3)0.0221 (5)
C60.10850 (17)0.25700 (10)0.6736 (2)0.0168 (5)
C70.23363 (16)0.26105 (9)0.4024 (2)0.0170 (5)
C80.19527 (16)0.33817 (9)0.3594 (2)0.0167 (5)
C90.07452 (17)0.35920 (9)0.3734 (3)0.0186 (5)
C100.03721 (17)0.42992 (10)0.3310 (3)0.0211 (5)
C110.12207 (17)0.48030 (10)0.2705 (2)0.0210 (5)
C120.24121 (17)0.46011 (9)0.2502 (3)0.0199 (5)
C130.28079 (16)0.38908 (10)0.2941 (2)0.0174 (5)
C140.50151 (16)0.41172 (10)0.2448 (3)0.0184 (5)
C150.51552 (17)0.47993 (9)0.3279 (3)0.0198 (5)
C160.61982 (17)0.52057 (10)0.3017 (3)0.0207 (5)
C170.71193 (17)0.49442 (10)0.1958 (3)0.0209 (5)
C180.69897 (16)0.42597 (10)0.1170 (3)0.0200 (5)
C190.59525 (16)0.38490 (10)0.1413 (3)0.0193 (5)
C200.21883 (19)0.14779 (10)0.5689 (3)0.0233 (6)
H10.223900.341600.727300.0220*
H20.113600.390500.960400.0260*
H2N0.4137 (18)0.3218 (13)0.255 (3)0.030 (6)*
H3−0.064800.333301.052300.0270*
H4−0.135800.230100.902300.0280*
H5−0.028400.182500.662200.0260*
H90.016700.324300.413000.0220*
H10−0.045000.443700.343000.0250*
H110.097800.529100.242900.0250*
H120.297400.494900.205600.0240*
H150.453600.498400.402300.0240*
H160.628200.567200.357400.0250*
H170.782800.522800.177500.0250*
H180.762100.407100.045500.0240*
H190.587900.338000.086900.0230*
H20A0.235700.123300.456600.0280*
H20B0.155200.120900.631400.0280*
H20C0.292200.148500.640900.0280*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0217 (6)0.0176 (6)0.0277 (8)0.0002 (5)0.0058 (6)−0.0024 (6)
N10.0235 (8)0.0128 (7)0.0179 (8)0.0006 (6)0.0020 (7)−0.0003 (6)
N20.0190 (8)0.0137 (7)0.0300 (10)−0.0008 (6)0.0053 (7)−0.0012 (7)
C10.0189 (8)0.0175 (8)0.0190 (9)−0.0007 (7)−0.0012 (8)0.0013 (8)
C20.0259 (10)0.0198 (9)0.0185 (9)0.0029 (7)−0.0031 (8)−0.0020 (8)
C30.0209 (9)0.0295 (10)0.0177 (9)0.0076 (8)0.0012 (8)0.0014 (8)
C40.0190 (8)0.0326 (10)0.0193 (10)−0.0017 (8)0.0004 (8)0.0039 (9)
C50.0258 (9)0.0203 (9)0.0202 (10)−0.0043 (7)−0.0014 (8)0.0007 (8)
C60.0203 (9)0.0162 (8)0.0139 (9)0.0023 (7)−0.0004 (8)0.0023 (7)
C70.0174 (8)0.0160 (8)0.0175 (9)−0.0032 (7)−0.0013 (8)−0.0033 (7)
C80.0194 (9)0.0165 (8)0.0142 (9)0.0001 (7)0.0008 (7)−0.0007 (7)
C90.0183 (9)0.0220 (9)0.0154 (9)−0.0023 (7)−0.0003 (7)−0.0001 (8)
C100.0190 (9)0.0241 (9)0.0201 (10)0.0027 (7)−0.0012 (8)0.0001 (8)
C110.0269 (10)0.0169 (8)0.0193 (10)0.0025 (7)−0.0037 (8)0.0014 (8)
C120.0243 (9)0.0173 (9)0.0180 (10)−0.0043 (7)0.0004 (8)0.0008 (8)
C130.0203 (8)0.0178 (8)0.0140 (9)−0.0003 (7)0.0003 (8)−0.0033 (7)
C140.0199 (8)0.0184 (8)0.0169 (9)−0.0013 (7)0.0009 (8)0.0033 (8)
C150.0208 (9)0.0197 (9)0.0189 (9)0.0008 (7)0.0021 (8)0.0005 (8)
C160.0248 (9)0.0162 (8)0.0210 (10)−0.0016 (7)−0.0036 (8)−0.0004 (7)
C170.0184 (9)0.0207 (9)0.0235 (10)−0.0023 (7)−0.0024 (8)0.0060 (8)
C180.0178 (9)0.0216 (9)0.0207 (10)0.0036 (7)0.0017 (8)0.0041 (8)
C190.0220 (9)0.0176 (8)0.0184 (9)0.0036 (7)−0.0002 (8)0.0004 (8)
C200.0339 (11)0.0132 (9)0.0227 (10)0.0012 (8)0.0017 (9)0.0018 (8)

Geometric parameters (Å, °)

O1—C71.239 (2)C15—C161.386 (3)
N1—C61.434 (2)C16—C171.384 (3)
N1—C71.356 (2)C17—C181.387 (3)
N1—C201.481 (2)C18—C191.383 (3)
N2—C131.387 (2)C1—H10.9500
N2—C141.401 (2)C2—H20.9500
N2—H2N0.85 (2)C3—H30.9500
C1—C21.380 (3)C4—H40.9500
C1—C61.392 (3)C5—H50.9500
C2—C31.388 (3)C9—H90.9500
C3—C41.381 (3)C10—H100.9500
C4—C51.394 (3)C11—H110.9500
C5—C61.383 (3)C12—H120.9500
C7—C81.499 (2)C15—H150.9500
C8—C91.396 (3)C16—H160.9500
C8—C131.414 (2)C17—H170.9500
C9—C101.387 (3)C18—H180.9500
C10—C111.390 (3)C19—H190.9500
C11—C121.379 (3)C20—H20A0.9800
C12—C131.402 (2)C20—H20B0.9800
C14—C191.391 (3)C20—H20C0.9800
C14—C151.398 (3)
C6—N1—C7125.87 (15)C2—C1—H1120.00
C6—N1—C20115.20 (15)C6—C1—H1120.00
C7—N1—C20116.98 (15)C1—C2—H2120.00
C13—N2—C14128.34 (15)C3—C2—H2120.00
C14—N2—H2N113.1 (14)C2—C3—H3120.00
C13—N2—H2N118.0 (14)C4—C3—H3120.00
C2—C1—C6120.08 (17)C3—C4—H4120.00
C1—C2—C3120.20 (18)C5—C4—H4120.00
C2—C3—C4119.6 (2)C4—C5—H5120.00
C3—C4—C5120.59 (18)C6—C5—H5120.00
C4—C5—C6119.44 (17)C8—C9—H9119.00
N1—C6—C5119.37 (16)C10—C9—H9119.00
N1—C6—C1120.51 (16)C9—C10—H10121.00
C1—C6—C5120.05 (17)C11—C10—H10121.00
O1—C7—C8120.32 (15)C10—C11—H11120.00
N1—C7—C8119.61 (15)C12—C11—H11120.00
O1—C7—N1120.06 (15)C11—C12—H12119.00
C9—C8—C13119.41 (15)C13—C12—H12119.00
C7—C8—C9120.71 (15)C14—C15—H15120.00
C7—C8—C13119.77 (16)C16—C15—H15120.00
C8—C9—C10121.43 (17)C15—C16—H16119.00
C9—C10—C11118.94 (17)C17—C16—H16119.00
C10—C11—C12120.68 (17)C16—C17—H17121.00
C11—C12—C13121.16 (17)C18—C17—H17121.00
N2—C13—C8119.76 (16)C17—C18—H18120.00
N2—C13—C12121.88 (16)C19—C18—H18120.00
C8—C13—C12118.33 (16)C14—C19—H19120.00
N2—C14—C15122.39 (17)C18—C19—H19120.00
C15—C14—C19118.82 (17)N1—C20—H20A109.00
N2—C14—C19118.68 (17)N1—C20—H20B109.00
C14—C15—C16119.94 (18)N1—C20—H20C109.00
C15—C16—C17121.10 (18)H20A—C20—H20B109.00
C16—C17—C18118.80 (17)H20A—C20—H20C109.00
C17—C18—C19120.77 (18)H20B—C20—H20C109.00
C14—C19—C18120.53 (18)
C7—N1—C6—C1−46.1 (3)N1—C7—C8—C9−35.8 (2)
C7—N1—C6—C5137.06 (19)N1—C7—C8—C13147.89 (16)
C20—N1—C6—C1117.39 (19)C7—C8—C9—C10−178.79 (18)
C20—N1—C6—C5−59.4 (2)C13—C8—C9—C10−2.5 (3)
C6—N1—C7—O1163.40 (16)C7—C8—C13—N2−0.1 (2)
C6—N1—C7—C8−18.0 (3)C7—C8—C13—C12178.12 (16)
C20—N1—C7—O10.1 (2)C9—C8—C13—N2−176.40 (16)
C20—N1—C7—C8178.73 (15)C9—C8—C13—C121.8 (2)
C14—N2—C13—C8−164.91 (18)C8—C9—C10—C111.1 (3)
C14—N2—C13—C1217.0 (3)C9—C10—C11—C121.0 (3)
C13—N2—C14—C1535.8 (3)C10—C11—C12—C13−1.7 (3)
C13—N2—C14—C19−148.16 (19)C11—C12—C13—N2178.41 (17)
C6—C1—C2—C31.1 (3)C11—C12—C13—C80.3 (3)
C2—C1—C6—N1−176.53 (17)N2—C14—C15—C16178.11 (19)
C2—C1—C6—C50.3 (3)C19—C14—C15—C162.1 (3)
C1—C2—C3—C4−1.4 (3)N2—C14—C19—C18−178.01 (19)
C2—C3—C4—C50.4 (3)C15—C14—C19—C18−1.9 (3)
C3—C4—C5—C61.0 (3)C14—C15—C16—C17−0.8 (3)
C4—C5—C6—N1175.56 (17)C15—C16—C17—C18−0.7 (3)
C4—C5—C6—C1−1.3 (3)C16—C17—C18—C191.0 (3)
O1—C7—C8—C9142.75 (18)C17—C18—C19—C140.3 (3)
O1—C7—C8—C13−33.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.85 (2)2.05 (2)2.684 (2)131.1 (18)
C9—H9···O1i0.952.573.350 (2)139
C2—H2···Cg2ii0.952.753.420 (2)129
C15—H15···Cg3iii0.952.673.503 (2)147
C20—H20A···Cg3i0.982.673.441 (2)136

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x, y, z+1; (iii) −x+1, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2103).

References

  • Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. (2001). Chem. Rev.101, 4071–4097. [PubMed]
  • 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.
  • Prins, L. J., Peinhoudt, D. N. & Timmerman, P. (2001). Angew. Chem. Int. Ed 40, 2383–2426. [PubMed]
  • Qi, J. Y., Chen, J., Yang, Q. Y., Zhou, Z. Y. & Chan, A. S. C. (2002). Acta Cryst. E58, o1232–o1233.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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