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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o541.
Published online 2008 January 30. doi:  10.1107/S1600536808003103
PMCID: PMC2960197

2-Methyl-N-(3-methyl­phen­yl)benzamide

Abstract

In the structure of the title compound (N3MP2MBA), C15H15NO, the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N3MP2MBA are similar to those in 2-methyl-N-phenyl­benzamide, N-(3,4-dimethyl­phen­yl)benzamide and other benzanilides. The amide group, –NHCO–, makes a dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. N—H(...)O hydrogen bonds give rise to infinite chains running along the b axis of the crystal structure.

Related literature

For related literature, see: Gowda et al. (2003 [triangle]; 2008a [triangle],b [triangle]).

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Object name is e-64-0o541-scheme1.jpg

Experimental

Crystal data

  • C15H15NO
  • M r = 225.28
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-64-0o541-efi1.jpg
  • a = 8.931 (2) Å
  • c = 15.816 (4) Å
  • V = 1261.5 (3) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.58 mm−1
  • T = 299 (2) K
  • 0.55 × 0.30 × 0.30 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: none
  • 1606 measured reflections
  • 1168 independent reflections
  • 1096 reflections with I > 2σ(I)
  • R int = 0.016
  • 3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.100
  • S = 1.07
  • 1168 reflections
  • 158 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.10 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003103/om2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003103/om2212Isup2.hkl

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the structures of N-aromatic amides, in the present work, the structure of N-(3-methylphenyl)-2-methylbenzamide (N3MP2MBA) has been determined (Gowda et al., 2003; 2008a; 2008b). In the structure of N3MP2MBA (Fig. 1), the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N2MP2MBA are similar to those in N-(phenyl)-2-methylbenzamide (Gowda et al., 2008a), N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The amide group –NHCO– has the dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. The packing diagram of N3MP2MBA molecules showing the hydrogen bonds N1—H1N···O1 (Table 1) involved in the formation of molecular chain is given in Fig. 2.

Experimental

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement

The NH atom was located in difference map and was refined with restrained geometry, viz. N—H distance was restrained to 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å A l l H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf"term set to zero.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Crystal data

C15H15NOZ = 4
Mr = 225.28F000 = 480
Tetragonal, P43Dx = 1.186 Mg m3
Hall symbol: P 4cwCu Kα radiation λ = 1.54180 Å
a = 8.931 (2) ÅCell parameters from 25 reflections
b = 8.931 (2) Åθ = 4.9–19.0º
c = 15.816 (4) ŵ = 0.58 mm1
α = 90ºT = 299 (2) K
β = 90ºPrism, colourless
γ = 90º0.55 × 0.30 × 0.30 mm
V = 1261.5 (3) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.016
Radiation source: fine-focus sealed tubeθmax = 66.8º
Monochromator: graphiteθmin = 5.0º
T = 299(2) Kh = −10→0
ω/2θ scansk = −10→0
Absorption correction: nonel = −18→3
1606 measured reflections3 standard reflections
1168 independent reflections every 120 min
1096 reflections with I > 2σ(I) intensity decay: 1.0%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100  w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0805P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1168 reflectionsΔρmax = 0.12 e Å3
158 parametersΔρmin = −0.10 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0069 (14)

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
C10.3124 (3)0.2503 (2)0.05561 (14)0.0534 (5)
C20.2079 (3)0.2607 (3)0.12012 (15)0.0601 (6)
H20.16290.35230.13170.072*
C30.1696 (3)0.1353 (3)0.16775 (15)0.0681 (7)
C40.2385 (4)0.0013 (3)0.1499 (2)0.0827 (9)
H40.2142−0.08330.18130.099*
C50.3424 (4)−0.0095 (3)0.0865 (2)0.0874 (9)
H50.3877−0.10110.07520.105*
C60.3802 (3)0.1149 (3)0.03921 (17)0.0718 (7)
H60.45120.1072−0.00360.086*
C70.3347 (2)0.5195 (2)0.01949 (14)0.0521 (5)
C80.3969 (3)0.6215 (3)−0.04697 (15)0.0576 (6)
C90.3085 (4)0.7335 (3)−0.08194 (17)0.0729 (7)
C100.3766 (6)0.8318 (4)−0.1386 (2)0.1034 (12)
H100.32000.9078−0.16300.124*
C110.5257 (7)0.8189 (4)−0.1590 (3)0.1172 (16)
H11A0.56920.8874−0.19580.141*
C120.6101 (5)0.7064 (5)−0.1257 (3)0.1091 (13)
H12A0.71020.6964−0.14080.131*
C130.5459 (4)0.6074 (3)−0.0694 (2)0.0774 (8)
H130.60330.5307−0.04630.093*
C140.0560 (4)0.1486 (5)0.2363 (2)0.0956 (10)
H14A−0.03760.18070.21270.115*
H14B0.08940.22060.27730.115*
H14C0.04310.05310.26320.115*
C150.1464 (4)0.7517 (5)−0.0604 (3)0.1053 (12)
H15A0.13610.7678−0.00070.126*
H15B0.09280.6629−0.07630.126*
H15C0.10640.8361−0.09040.126*
N10.3505 (2)0.3731 (2)0.00353 (13)0.0561 (5)
H1N0.392 (3)0.350 (3)−0.0422 (14)0.067*
O10.2763 (2)0.56893 (19)0.08395 (11)0.0681 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0613 (12)0.0547 (12)0.0444 (11)−0.0074 (9)−0.0062 (10)−0.0018 (9)
C20.0662 (13)0.0625 (13)0.0515 (13)−0.0094 (10)−0.0007 (11)0.0011 (11)
C30.0790 (16)0.0749 (16)0.0504 (14)−0.0251 (13)−0.0092 (12)0.0083 (12)
C40.112 (2)0.0683 (16)0.0680 (17)−0.0192 (15)−0.0136 (17)0.0189 (14)
C50.123 (2)0.0562 (14)0.083 (2)0.0044 (15)−0.007 (2)0.0070 (15)
C60.0897 (18)0.0639 (14)0.0619 (16)0.0042 (12)0.0023 (14)−0.0021 (12)
C70.0558 (11)0.0558 (11)0.0447 (11)−0.0033 (9)−0.0023 (9)−0.0026 (9)
C80.0721 (14)0.0517 (12)0.0490 (12)−0.0063 (10)0.0031 (11)−0.0049 (10)
C90.102 (2)0.0610 (14)0.0560 (15)0.0059 (13)−0.0007 (14)0.0014 (12)
C100.173 (4)0.0676 (17)0.070 (2)0.008 (2)0.016 (2)0.0166 (15)
C110.180 (4)0.078 (2)0.093 (3)−0.043 (3)0.047 (3)0.003 (2)
C120.111 (3)0.093 (2)0.123 (3)−0.033 (2)0.047 (3)−0.007 (2)
C130.0777 (17)0.0716 (16)0.0828 (19)−0.0131 (13)0.0141 (15)−0.0023 (14)
C140.107 (2)0.112 (2)0.0678 (18)−0.0414 (19)0.0137 (18)0.0095 (18)
C150.105 (3)0.125 (3)0.086 (2)0.038 (2)−0.011 (2)0.012 (2)
N10.0679 (12)0.0564 (10)0.0440 (9)−0.0042 (8)0.0088 (9)−0.0027 (8)
O10.0946 (12)0.0628 (10)0.0468 (9)0.0015 (9)0.0096 (9)−0.0054 (8)

Geometric parameters (Å, °)

C1—C61.377 (4)C9—C101.394 (5)
C1—C21.386 (3)C9—C151.496 (5)
C1—N11.414 (3)C10—C111.375 (7)
C2—C31.392 (3)C10—H100.9300
C2—H20.9300C11—C121.361 (7)
C3—C41.375 (5)C11—H11A0.9300
C3—C141.490 (5)C12—C131.380 (5)
C4—C51.369 (5)C12—H12A0.9300
C4—H40.9300C13—H130.9300
C5—C61.381 (4)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—O11.227 (3)C15—H15A0.9600
C7—N11.339 (3)C15—H15B0.9600
C7—C81.498 (3)C15—H15C0.9600
C8—C131.382 (4)N1—H1N0.837 (18)
C8—C91.389 (4)
C6—C1—C2119.6 (2)C11—C10—C9121.4 (4)
C6—C1—N1117.8 (2)C11—C10—H10119.3
C2—C1—N1122.6 (2)C9—C10—H10119.3
C1—C2—C3120.6 (2)C12—C11—C10120.5 (3)
C1—C2—H2119.7C12—C11—H11A119.8
C3—C2—H2119.7C10—C11—H11A119.8
C4—C3—C2118.6 (3)C11—C12—C13119.5 (4)
C4—C3—C14121.6 (3)C11—C12—H12A120.2
C2—C3—C14119.8 (3)C13—C12—H12A120.2
C5—C4—C3121.0 (3)C12—C13—C8120.4 (3)
C5—C4—H4119.5C12—C13—H13119.8
C3—C4—H4119.5C8—C13—H13119.8
C4—C5—C6120.4 (3)C3—C14—H14A109.5
C4—C5—H5119.8C3—C14—H14B109.5
C6—C5—H5119.8H14A—C14—H14B109.5
C1—C6—C5119.8 (3)C3—C14—H14C109.5
C1—C6—H6120.1H14A—C14—H14C109.5
C5—C6—H6120.1H14B—C14—H14C109.5
O1—C7—N1123.5 (2)C9—C15—H15A109.5
O1—C7—C8121.5 (2)C9—C15—H15B109.5
N1—C7—C8114.97 (19)H15A—C15—H15B109.5
C13—C8—C9120.7 (3)C9—C15—H15C109.5
C13—C8—C7118.8 (2)H15A—C15—H15C109.5
C9—C8—C7120.4 (2)H15B—C15—H15C109.5
C8—C9—C10117.5 (3)C7—N1—C1128.5 (2)
C8—C9—C15122.5 (3)C7—N1—H1N117 (2)
C10—C9—C15120.0 (3)C1—N1—H1N115 (2)
C6—C1—C2—C3−0.7 (3)C7—C8—C9—C10175.1 (3)
N1—C1—C2—C3177.5 (2)C13—C8—C9—C15179.2 (3)
C1—C2—C3—C40.5 (4)C7—C8—C9—C15−4.4 (4)
C1—C2—C3—C14−179.5 (3)C8—C9—C10—C11−0.1 (5)
C2—C3—C4—C5−0.2 (4)C15—C9—C10—C11179.4 (4)
C14—C3—C4—C5179.8 (3)C9—C10—C11—C121.7 (6)
C3—C4—C5—C60.1 (5)C10—C11—C12—C13−1.7 (7)
C2—C1—C6—C50.7 (4)C11—C12—C13—C80.3 (6)
N1—C1—C6—C5−177.7 (3)C9—C8—C13—C121.3 (5)
C4—C5—C6—C1−0.4 (5)C7—C8—C13—C12−175.2 (3)
O1—C7—C8—C13122.6 (3)O1—C7—N1—C1−3.0 (4)
N1—C7—C8—C13−56.2 (3)C8—C7—N1—C1175.7 (2)
O1—C7—C8—C9−53.9 (3)C6—C1—N1—C7−159.7 (2)
N1—C7—C8—C9127.4 (2)C2—C1—N1—C722.0 (4)
C13—C8—C9—C10−1.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.837 (18)2.10 (2)2.908 (3)163 (3)

Symmetry codes: (i) −y+1, x, z−1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2212).

References

  • Enraf–Nonius (1996). CAD-4-PC Enraf–Nonius, Delft, The Netherlands.
  • Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o383. [PMC free article] [PubMed]
  • Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.
  • Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o340. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Stoe & Cie (1987). REDU4 Stoe & Cie GmbH, Darmstadt, Germany.

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