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

Yan, Z.-W.; Li, Y.-H.; Xiao, Q.; Zhao, L.; Zhu, H.-J.

doi:10.1107/S1600536810022361

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1679

doi:10.1107/S1600536810022361

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

Zhang-Wei Yan,^a Yu-Hao Li,^a Qi Xiao,^a Liang Zhao ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 1 June 2010; accepted 10 June 2010; online 16 June 2010)

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 ). For the use of related compounds in N-substituted glycine peptoid oligomers, see Shah et al. (2008 ). For a related structure, see: Li et al. (2008 ). For bond-length data, see: Allen et al. (1987 )

Experimental

Crystal data

C₁₀H₁₃NO
M_r = 163.21
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.180
S = 1.00
1726 reflections
112 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯Oⁱ	0.96	2.51	3.442 (4)	165
C1—H1A⋯Oⁱⁱ	0.93	2.60	3.414 (4)	145
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022361/im2208sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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). For the use of related compounds in N-substituted glycine peptoid oligomers, see Shah et al. (2008). For a related structure, see: Li et al. (2008). For bond-length data, see: Allen et al. (1987)

Experimental top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo,1995); 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

	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.

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

Crystal data top

C₁₀H₁₃NO	F(000) = 352
M_r = 163.21	D_x = 1.142 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 328 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.288 (2) Å	Cell parameters from 25 reflections
b = 6.900 (1) Å	θ = 9–13°
c = 12.234 (2) Å	µ = 0.07 mm⁻¹
β = 94.88 (3)°	T = 293 K
V = 949.5 (3) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1044 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Graphite monochromator	θ_max = 25.3°, θ_min = 2.4°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
T_min = 0.978, T_max = 0.993	l = −14→14
3465 measured reflections	3 standard reflections every 200 reflections
1726 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.060P)² + 0.550P] where P = (F_o² + 2F_c²)/3
1726 reflections	(Δ/σ)_max < 0.001
112 parameters	Δρ_max = 0.32 e Å⁻³
4 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₀H₁₃NO	V = 949.5 (3) Å³
M_r = 163.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.288 (2) Å	µ = 0.07 mm⁻¹
b = 6.900 (1) Å	T = 293 K
c = 12.234 (2) Å	0.30 × 0.20 × 0.10 mm
β = 94.88 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1044 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.055
T_min = 0.978, T_max = 0.993	3 standard reflections every 200 reflections
3465 measured reflections	intensity decay: 1%
1726 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	4 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
1726 reflections	Δρ_min = −0.16 e Å⁻³
112 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
N	0.8267 (3)	0.3421 (5)	−0.0762 (2)	0.0917 (9)
O	0.9121 (2)	0.5682 (4)	−0.1656 (2)	0.1110 (10)
C1	0.8287 (3)	0.1854 (5)	0.1029 (3)	0.0744 (9)
H1A	0.9111	0.1976	0.1095	0.089*
C2	0.7737 (3)	0.0925 (4)	0.1832 (2)	0.0696 (8)
H2A	0.8181	0.0387	0.2432	0.083*
C3	0.6508 (3)	0.0794 (4)	0.1741 (2)	0.0660 (8)
H3A	0.6121	0.0177	0.2285	0.079*
C4	0.5867 (3)	0.1571 (4)	0.0853 (2)	0.0629 (8)
H4A	0.5043	0.1465	0.0801	0.075*
C5	0.6408 (2)	0.2526 (4)	0.0015 (2)	0.0554 (7)
C6	0.7649 (3)	0.2603 (5)	0.0137 (2)	0.0682 (8)
C7	0.5689 (3)	0.3319 (5)	−0.0977 (2)	0.0733 (9)
H7A	0.5852	0.4676	−0.1048	0.110*
H7B	0.4858	0.3138	−0.0895	0.110*
H7C	0.5897	0.2648	−0.1621	0.110*
C8	0.8631 (3)	0.1932 (7)	−0.1620 (3)	0.1025 (12)
H8A	0.9102	0.2565	−0.2132	0.154*
H8B	0.7930	0.1397	−0.2006	0.154*
H8C	0.9087	0.0911	−0.1255	0.154*
C9	0.8569 (3)	0.5129 (7)	−0.0876 (3)	0.0931 (10)
C10	0.8173 (3)	0.6500 (5)	0.0004 (3)	0.0896 (10)
H10A	0.8712	0.6398	0.0652	0.134*
H10B	0.7386	0.6155	0.0177	0.134*
H10C	0.8171	0.7808	−0.0264	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0813 (19)	0.107 (2)	0.089 (2)	−0.0143 (17)	0.0181 (15)	0.0186 (16)
O	0.0849 (16)	0.150 (2)	0.1002 (17)	−0.0239 (16)	0.0217 (13)	0.0430 (16)
C1	0.0646 (18)	0.081 (2)	0.077 (2)	−0.0093 (16)	0.0022 (16)	0.0066 (18)
C2	0.090 (2)	0.0613 (17)	0.0576 (17)	−0.0028 (17)	0.0063 (15)	0.0046 (14)
C3	0.086 (2)	0.0624 (17)	0.0519 (15)	−0.0241 (16)	0.0178 (15)	0.0047 (14)
C4	0.0630 (17)	0.0684 (17)	0.0600 (17)	−0.0176 (14)	0.0214 (14)	−0.0081 (15)
C5	0.0601 (16)	0.0554 (15)	0.0517 (14)	−0.0082 (13)	0.0109 (12)	−0.0029 (12)
C6	0.0639 (18)	0.077 (2)	0.0650 (18)	−0.0171 (16)	0.0108 (14)	0.0132 (16)
C7	0.0699 (18)	0.083 (2)	0.0683 (18)	−0.0097 (17)	0.0101 (15)	0.0085 (17)
C8	0.083 (2)	0.159 (4)	0.070 (2)	−0.011 (2)	0.0350 (17)	0.007 (2)
C9	0.073 (2)	0.122 (3)	0.085 (2)	−0.017 (2)	0.0104 (16)	0.0221 (18)
C10	0.097 (2)	0.0670 (19)	0.106 (2)	−0.0223 (18)	0.0166 (19)	0.0247 (16)

Geometric parameters (Å, º) top

N—C9	1.238 (5)	C5—C6	1.396 (4)
N—C6	1.465 (4)	C5—C7	1.505 (4)
N—C8	1.549 (5)	C7—H7A	0.9600
O—C9	1.243 (4)	C7—H7B	0.9600
C1—C6	1.358 (4)	C7—H7C	0.9600
C1—C2	1.366 (4)	C8—H8A	0.9600
C1—H1A	0.9300	C8—H8B	0.9600
C2—C3	1.384 (4)	C8—H8C	0.9600
C2—H2A	0.9300	C9—C10	1.528 (5)
C3—C4	1.363 (4)	C10—H10A	0.9600
C3—H3A	0.9300	C10—H10B	0.9600
C4—C5	1.401 (3)	C10—H10C	0.9600
C4—H4A	0.9300

C9—N—C6	127.2 (3)	C5—C7—H7A	109.5
C9—N—C8	117.6 (3)	C5—C7—H7B	109.5
C6—N—C8	115.1 (3)	H7A—C7—H7B	109.5
C6—C1—C2	120.9 (3)	C5—C7—H7C	109.5
C6—C1—H1A	119.5	H7A—C7—H7C	109.5
C2—C1—H1A	119.5	H7B—C7—H7C	109.5
C1—C2—C3	119.1 (3)	N—C8—H8A	109.5
C1—C2—H2A	120.4	N—C8—H8B	109.5
C3—C2—H2A	120.4	H8A—C8—H8B	109.5
C4—C3—C2	119.9 (3)	N—C8—H8C	109.5
C4—C3—H3A	120.0	H8A—C8—H8C	109.5
C2—C3—H3A	120.0	H8B—C8—H8C	109.5
C3—C4—C5	122.2 (3)	N—C9—O	122.6 (4)
C3—C4—H4A	118.9	N—C9—C10	114.2 (3)
C5—C4—H4A	118.9	O—C9—C10	123.1 (4)
C6—C5—C4	115.8 (3)	C9—C10—H10A	109.5
C6—C5—C7	122.6 (2)	C9—C10—H10B	109.5
C4—C5—C7	121.5 (2)	H10A—C10—H10B	109.5
C1—C6—C5	122.0 (3)	C9—C10—H10C	109.5
C1—C6—N	119.8 (3)	H10A—C10—H10C	109.5
C5—C6—N	118.1 (3)	H10B—C10—H10C	109.5

C6—C1—C2—C3	−1.7 (5)	C7—C5—C6—N	−2.5 (4)
C1—C2—C3—C4	0.6 (5)	C9—N—C6—C1	−91.7 (5)
C2—C3—C4—C5	−0.4 (4)	C8—N—C6—C1	84.8 (4)
C3—C4—C5—C6	1.1 (4)	C9—N—C6—C5	91.8 (4)
C3—C4—C5—C7	178.0 (3)	C8—N—C6—C5	−91.7 (4)
C2—C1—C6—C5	2.4 (5)	C6—N—C9—O	178.1 (3)
C2—C1—C6—N	−174.0 (3)	C8—N—C9—O	1.6 (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—C10	179.9 (3)
C4—C5—C6—N	174.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···Oⁱ	0.96	2.51	3.442 (4)	165
C1—H1A···Oⁱⁱ	0.93	2.60	3.414 (4)	145

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO
M_r	163.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.288 (2), 6.900 (1), 12.234 (2)
β (°)	94.88 (3)
V (Å³)	949.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.978, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	3465, 1726, 1044
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.180, 1.00
No. of reflections	1726
No. of parameters	112
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···Oⁱ	0.96	2.51	3.442 (4)	165
C1—H1A···Oⁱⁱ	0.93	2.60	3.414 (4)	145

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

Acknowledgements

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

References

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