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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1679.
Published online 2010 June 16. doi:  10.1107/S1600536810022361
PMCID: PMC3007068

N-Methyl-N-(2-methyl­phen­yl)acetamide

Abstract

In the title compound, C10H13NO, the N atom and the methyl group are almost coplanar with the benzene ring to which they are bonded [deviations of 0.131 (1) and 0.038 (1) Å, respectively, from the ring plane]. In the crystal structure, inter­molecular C—H(...)O hydrogen bonds form a three-dimensional network. Mol­ecules are stacked parallel to the b-axis direction.

Related literature

For the use of related compounds as inter­mediates in syntheses of ligands for human β-amyloid plaques and for the preparation of the title compound, see Cai et al. (2007 [triangle]). For the use of related compounds in N-substituted glycine peptoid oligomers, see Shah et al. (2008 [triangle]). For a related structure, see: Li et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle])

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Object name is e-66-o1679-scheme1.jpg

Experimental

Crystal data

  • C10H13NO
  • M r = 163.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1679-efi1.jpg
  • a = 11.288 (2) Å
  • b = 6.900 (1) Å
  • c = 12.234 (2) Å
  • β = 94.88 (3)°
  • V = 949.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.978, T max = 0.993
  • 3465 measured reflections
  • 1726 independent reflections
  • 1044 reflections with I > 2σ(I)
  • R int = 0.055
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.180
  • S = 1.00
  • 1726 reflections
  • 112 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 [triangle]); 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 I, global. DOI: 10.1107/S1600536810022361/im2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022361/im2208Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound, (I), contains acetyl group, which can react with different groups to prepare various function organic compounds. It is a kind of aromatic organic intermediate which can be used for many fields such as medicine. (Cai et al., 2007). Herein we report its crystal structure.

In the molecule of (I), (Fig.1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The N and C7 atoms are situated in the same plane as the benzene ring they are bonded to. The C—H···O intermolecular hydrogen bonds form a three dimensional network, which seems to be very effective in the stabilization of the crystal structure.

As can be seen from the packing diagram, (Fig. 2), the molecules are stacked along the b axis. There are also weak π-π interactions of benzene rings with a face-to-face stacking distance of 5.991 (4) Å.

Experimental

The title compound, (I) was prepared by the literature method (Cai et al., 2007). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in ethyl acetate (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Refinement

All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93 Å and 0.96 Å for aromatic H and methyl group H, respectively. The Uiso(H) = xUeq(C), where x = 1.2 for aromatic H, and x = 1.5 for other H.

Figures

Fig. 1.
Molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C10H13NOF(000) = 352
Mr = 163.21Dx = 1.142 Mg m3
Monoclinic, P21/nMelting point: 328 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 11.288 (2) ÅCell parameters from 25 reflections
b = 6.900 (1) Åθ = 9–13°
c = 12.234 (2) ŵ = 0.07 mm1
β = 94.88 (3)°T = 293 K
V = 949.5 (3) Å3Block, colourless
Z = 40.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer1044 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
graphiteθmax = 25.3°, θmin = 2.4°
ω/2θ scansh = 0→13
Absorption correction: ψ scan (North et al., 1968)k = −8→8
Tmin = 0.978, Tmax = 0.993l = −14→14
3465 measured reflections3 standard reflections every 200 reflections
1726 independent reflections intensity decay: 1%

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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.060P)2 + 0.550P] where P = (Fo2 + 2Fc2)/3
1726 reflections(Δ/σ)max < 0.001
112 parametersΔρmax = 0.32 e Å3
4 restraintsΔρmin = −0.16 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
N0.8267 (3)0.3421 (5)−0.0762 (2)0.0917 (9)
O0.9121 (2)0.5682 (4)−0.1656 (2)0.1110 (10)
C10.8287 (3)0.1854 (5)0.1029 (3)0.0744 (9)
H1A0.91110.19760.10950.089*
C20.7737 (3)0.0925 (4)0.1832 (2)0.0696 (8)
H2A0.81810.03870.24320.083*
C30.6508 (3)0.0794 (4)0.1741 (2)0.0660 (8)
H3A0.61210.01770.22850.079*
C40.5867 (3)0.1571 (4)0.0853 (2)0.0629 (8)
H4A0.50430.14650.08010.075*
C50.6408 (2)0.2526 (4)0.0015 (2)0.0554 (7)
C60.7649 (3)0.2603 (5)0.0137 (2)0.0682 (8)
C70.5689 (3)0.3319 (5)−0.0977 (2)0.0733 (9)
H7A0.58520.4676−0.10480.110*
H7B0.48580.3138−0.08950.110*
H7C0.58970.2648−0.16210.110*
C80.8631 (3)0.1932 (7)−0.1620 (3)0.1025 (12)
H8A0.91020.2565−0.21320.154*
H8B0.79300.1397−0.20060.154*
H8C0.90870.0911−0.12550.154*
C90.8569 (3)0.5129 (7)−0.0876 (3)0.0931 (10)
C100.8173 (3)0.6500 (5)0.0004 (3)0.0896 (10)
H10A0.87120.63980.06520.134*
H10B0.73860.61550.01770.134*
H10C0.81710.7808−0.02640.134*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N0.0813 (19)0.107 (2)0.089 (2)−0.0143 (17)0.0181 (15)0.0186 (16)
O0.0849 (16)0.150 (2)0.1002 (17)−0.0239 (16)0.0217 (13)0.0430 (16)
C10.0646 (18)0.081 (2)0.077 (2)−0.0093 (16)0.0022 (16)0.0066 (18)
C20.090 (2)0.0613 (17)0.0576 (17)−0.0028 (17)0.0063 (15)0.0046 (14)
C30.086 (2)0.0624 (17)0.0519 (15)−0.0241 (16)0.0178 (15)0.0047 (14)
C40.0630 (17)0.0684 (17)0.0600 (17)−0.0176 (14)0.0214 (14)−0.0081 (15)
C50.0601 (16)0.0554 (15)0.0517 (14)−0.0082 (13)0.0109 (12)−0.0029 (12)
C60.0639 (18)0.077 (2)0.0650 (18)−0.0171 (16)0.0108 (14)0.0132 (16)
C70.0699 (18)0.083 (2)0.0683 (18)−0.0097 (17)0.0101 (15)0.0085 (17)
C80.083 (2)0.159 (4)0.070 (2)−0.011 (2)0.0350 (17)0.007 (2)
C90.073 (2)0.122 (3)0.085 (2)−0.017 (2)0.0104 (16)0.0221 (18)
C100.097 (2)0.0670 (19)0.106 (2)−0.0223 (18)0.0166 (19)0.0247 (16)

Geometric parameters (Å, °)

N—C91.238 (5)C5—C61.396 (4)
N—C61.465 (4)C5—C71.505 (4)
N—C81.549 (5)C7—H7A0.9600
O—C91.243 (4)C7—H7B0.9600
C1—C61.358 (4)C7—H7C0.9600
C1—C21.366 (4)C8—H8A0.9600
C1—H1A0.9300C8—H8B0.9600
C2—C31.384 (4)C8—H8C0.9600
C2—H2A0.9300C9—C101.528 (5)
C3—C41.363 (4)C10—H10A0.9600
C3—H3A0.9300C10—H10B0.9600
C4—C51.401 (3)C10—H10C0.9600
C4—H4A0.9300
C9—N—C6127.2 (3)C5—C7—H7A109.5
C9—N—C8117.6 (3)C5—C7—H7B109.5
C6—N—C8115.1 (3)H7A—C7—H7B109.5
C6—C1—C2120.9 (3)C5—C7—H7C109.5
C6—C1—H1A119.5H7A—C7—H7C109.5
C2—C1—H1A119.5H7B—C7—H7C109.5
C1—C2—C3119.1 (3)N—C8—H8A109.5
C1—C2—H2A120.4N—C8—H8B109.5
C3—C2—H2A120.4H8A—C8—H8B109.5
C4—C3—C2119.9 (3)N—C8—H8C109.5
C4—C3—H3A120.0H8A—C8—H8C109.5
C2—C3—H3A120.0H8B—C8—H8C109.5
C3—C4—C5122.2 (3)N—C9—O122.6 (4)
C3—C4—H4A118.9N—C9—C10114.2 (3)
C5—C4—H4A118.9O—C9—C10123.1 (4)
C6—C5—C4115.8 (3)C9—C10—H10A109.5
C6—C5—C7122.6 (2)C9—C10—H10B109.5
C4—C5—C7121.5 (2)H10A—C10—H10B109.5
C1—C6—C5122.0 (3)C9—C10—H10C109.5
C1—C6—N119.8 (3)H10A—C10—H10C109.5
C5—C6—N118.1 (3)H10B—C10—H10C109.5
C6—C1—C2—C3−1.7 (5)C7—C5—C6—N−2.5 (4)
C1—C2—C3—C40.6 (5)C9—N—C6—C1−91.7 (5)
C2—C3—C4—C5−0.4 (4)C8—N—C6—C184.8 (4)
C3—C4—C5—C61.1 (4)C9—N—C6—C591.8 (4)
C3—C4—C5—C7178.0 (3)C8—N—C6—C5−91.7 (4)
C2—C1—C6—C52.4 (5)C6—N—C9—O178.1 (3)
C2—C1—C6—N−174.0 (3)C8—N—C9—O1.6 (6)
C4—C5—C6—C1−2.1 (4)C6—N—C9—C10−3.6 (5)
C7—C5—C6—C1−179.0 (3)C8—N—C9—C10179.9 (3)
C4—C5—C6—N174.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7C···Oi0.962.513.442 (4)165
C1—H1A···Oii0.932.603.414 (4)145

Symmetry codes: (i) −x+3/2, y−1/2, −z−1/2; (ii) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2208).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Cai, L. S., Cuevas, J., Temme, S., Herman, M. M., Dagostin, C., Widdowson, D. A., Innis, R. B. & Pike, V. W. (2007). J. Med. Chem.50, 4746–4758. [PubMed]
  • Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Li, Y.-H., Liu, R., Zhang, X.-N. & Zhu, H.-J. (2008). Acta Cryst. E64, o533. [PMC free article] [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Shah, N. H., Butterfoss, G. L., Nguyen, K., Yoo, B., Bonneau, R., Rabenstein, D. L. & Kirshenbaum, K. (2008). J. Am. Chem Soc.130, 16622–16632. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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