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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1107

2-Anilino-N-methyl-N-phenyl­benzamide

aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 16 March 2009; accepted 6 April 2009; online 25 April 2009)

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[Martín, A., Mesa, M., Docampo, M. L., Gómez, V. & Pellón, R. F. (2006). Synth. Commun. 36, 271-277.]); Charton et al. (2006[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.]). For related structures, see: Du et al. (2009[Du, P., Jiang, X. K. & Li, Z. T. (2009). Tetrahedron Lett. 50, 316-319.]); Qi et al. (2002[Qi, J. Y., Chen, J., Yang, Q. Y., Zhou, Z. Y. & Chan, A. S. C. (2002). Acta Cryst. E58, o1232-o1233.]). For further information on mol­ecular recognition and self-assembly, see: Brunsveld et al. (2001[Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. (2001). Chem. Rev. 101, 4071-4097.]); Prins et al. (2001[Prins, L. J., Peinhoudt, D. N. & Timmerman, P. (2001). Angew. Chem. Int. Ed. 40, 2383-2426.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O

  • Mr = 302.36

  • Orthorhombic, P n a 21

  • 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)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯O1 0.85 (2) 2.05 (2) 2.684 (2) 131.1 (18)
C9—H9⋯O1i 0.95 2.57 3.350 (2) 139
C2—H2⋯Cg2ii 0.95 2.75 3.420 (2) 129
C15—H15⋯Cg3iii 0.95 2.67 3.503 (2) 147
C20—H20ACg3i 0.98 2.67 3.441 (2) 136
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (ii) x, y, z+1; (iii) [-x+1, -y+1, z+{\script{1\over 2}}]. Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004[Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

For the synthesis of the title compound, see: Martín et al. (2006); Charton et al. (2006). For related structures, see: Du et al. (2009); Qi et al. (2002). For further information on molecular recognition and self-assembly, see: Brunsveld et al. (2001); Prins et al. (2001). Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.

Experimental top

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 top

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%)].

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] 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.
2-Anilino-N-methyl-N-phenylbenzamide top
Crystal data top
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 top
Rigaku Spider
diffractometer
1803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.5°, θmin = 3.4°
ω scansh = 1414
12048 measured reflectionsk = 2320
1887 independent reflectionsl = 99
Refinement top
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 = 1.18 w = 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
Crystal data top
C20H18N2OV = 1528.4 (6) Å3
Mr = 302.36Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 11.086 (2) ŵ = 0.08 mm1
b = 18.150 (4) ÅT = 93 K
c = 7.5962 (17) Å0.40 × 0.30 × 0.20 mm
Data collection top
Rigaku Spider
diffractometer
1803 reflections with I > 2σ(I)
12048 measured reflectionsRint = 0.034
1887 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0331 restraint
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.18Δρmax = 0.37 e Å3
1887 reflectionsΔρmin = 0.18 e Å3
213 parameters
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 > 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) top
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)
C30.02095 (17)0.31422 (11)0.9550 (3)0.0227 (5)
C40.06272 (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)*
H30.064800.333301.052300.0270*
H40.135800.230100.902300.0280*
H50.028400.182500.662200.0260*
H90.016700.324300.413000.0220*
H100.045000.443700.343000.0250*
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) top
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, º) top
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—C146.1 (3)N1—C7—C8—C935.8 (2)
C7—N1—C6—C5137.06 (19)N1—C7—C8—C13147.89 (16)
C20—N1—C6—C1117.39 (19)C7—C8—C9—C10178.79 (18)
C20—N1—C6—C559.4 (2)C13—C8—C9—C102.5 (3)
C6—N1—C7—O1163.40 (16)C7—C8—C13—N20.1 (2)
C6—N1—C7—C818.0 (3)C7—C8—C13—C12178.12 (16)
C20—N1—C7—O10.1 (2)C9—C8—C13—N2176.40 (16)
C20—N1—C7—C8178.73 (15)C9—C8—C13—C121.8 (2)
C14—N2—C13—C8164.91 (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—C131.7 (3)
C13—N2—C14—C19148.16 (19)C11—C12—C13—N2178.41 (17)
C6—C1—C2—C31.1 (3)C11—C12—C13—C80.3 (3)
C2—C1—C6—N1176.53 (17)N2—C14—C15—C16178.11 (19)
C2—C1—C6—C50.3 (3)C19—C14—C15—C162.1 (3)
C1—C2—C3—C41.4 (3)N2—C14—C19—C18178.01 (19)
C2—C3—C4—C50.4 (3)C15—C14—C19—C181.9 (3)
C3—C4—C5—C61.0 (3)C14—C15—C16—C170.8 (3)
C4—C5—C6—N1175.56 (17)C15—C16—C17—C180.7 (3)
C4—C5—C6—C11.3 (3)C16—C17—C18—C191.0 (3)
O1—C7—C8—C9142.75 (18)C17—C18—C19—C140.3 (3)
O1—C7—C8—C1333.5 (2)
Hydrogen-bond geometry (Å, º) top
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) x1/2, y+1/2, z; (ii) x, y, z+1; (iii) x+1, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H18N2O
Mr302.36
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)93
a, b, c (Å)11.086 (2), 18.150 (4), 7.5962 (17)
V3)1528.4 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerRigaku Spider
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12048, 1887, 1803
Rint0.034
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.080, 1.18
No. of reflections1887
No. of parameters213
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.18

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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) x1/2, y+1/2, z; (ii) x, y, z+1; (iii) x+1, y+1, z+1/2.
 

Acknowledgements

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).

References

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Volume 65| Part 5| May 2009| Page o1107
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