N-(2,6-Dimethyl­phen­yl)-2-methyl­acetamide

Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536807068419

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o380

doi:10.1107/S1600536807068419

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N-(2,6-Dimethylphenyl)-2-methylacetamide

B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 19 December 2007; accepted 25 December 2007; online 9 January 2008)

The structure of the title compound (26DMPMA), C₁₁H₁₅NO, is closely related to the side-chain unsubstituted N-(2,6-dimethylphenyl)acetamide and side-chain substituted N-(2,6-dimethylphenyl)-2,2,2-trimethylacetamide and 2-chloro-N-(2,6-dimethylphenyl)acetamide, with slightly different bond parameters. The molecules in 26DMPMA are linked into chains through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2004 , 2008 ); Gowda, Foro & Fuess (2007 ); Gowda, Svoboda & Fuess (2007 ).

Experimental

Crystal data

C₁₁H₁₅NO
M_r = 177.24
Monoclinic, P 2₁ /n
a = 4.7915 (7) Å
b = 11.593 (2) Å
c = 17.966 (3) Å
β = 96.11 (2)°
V = 992.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.50 × 0.14 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Ltd, Köln, Germany.]$ )T_min = 0.951, T_max = 0.989
7811 measured reflections
2005 independent reflections
1262 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 0.95
2005 reflections
164 parameters
Only H-atom coordinates refined
Δρ_max = 0.17 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
N1—H1N⋯O1ⁱ	0.889 (14)	2.065 (14)	2.9352 (15)	165.9 (12)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Ltd, Köln, Germany.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068419/dn2305sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068419/dn2305Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-methyl-N-(2,6-dimethylphenyl)- acetamide (26DMPMA) (Fig. 1) has been determined as part of a study of the effect of ring and side chain substitutions on the solid state geometry of biologically significant compounds such as acetanilides (Gowda, Foro & Fuess, 2007); Gowda, Svoboda & Fuess, 2007); Gowda et al., 2008). The structure of 26DMPMA is closely related to the side chain unsubstituted N-(2,6-dimethylphenyl)-acetamide (26DMPA) (Gowda, Foro & Fuess, 2007) and side chain substituted, 2,2,2-trimethyl-N-(2,6-dimethylphenyl)-acetamide (26DMPTMA) (Gowda, Svoboda & Fuess, 2007) and 2-chloro-N-(2,6-dimethylphenyl)- cetamide (26DMPCA) (Gowda et al., 2008). The bond parameters in 26DMPMA are similar to those in 26DMPA, 26DMPTMA, 26DMPCA and other acetanilides (Gowda, Foro & Fuess, 2007; Gowda, Svoboda & Fuess, 2007; Gowda et al., 2008). The molecules in 26DMPMA are linked into infinite chains through N—H···O hydrogen bonding (Table 1 and Fig.2).

Related literature top

For related literature, see: Gowda et al. (2004, 2008); Gowda, Foro & Fuess (2007); Gowda, Svoboda & Fuess (2007).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2004). The purity of the compound was checked by determining its melting point. The compound was further characterized by recording its infrared and NMR spectra (Gowda et al., 2004). Single crystals of the title compound were obtained from a slow evaporation of an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the formation of a chain. Hydrogen bonds are represented as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

N-(2,6-Dimethylphenyl)-2-methylacetamide top

Crystal data top

C₁₁H₁₅NO	F(000) = 384
M_r = 177.24	D_x = 1.186 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1603 reflections
a = 4.7915 (7) Å	θ = 2.1–24.9°
b = 11.593 (2) Å	µ = 0.08 mm⁻¹
c = 17.966 (3) Å	T = 100 K
β = 96.11 (2)°	Needle, colourless
V = 992.3 (3) Å³	0.50 × 0.14 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2005 independent reflections
Radiation source: fine-focus sealed tube	1262 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2007); empirical (using intensity measurements) absorption correction using spherical harmonics implemented in SCALE3 ABSPACK scaling algorithm]	h = −5→5
T_min = 0.951, T_max = 0.989	k = −13→14
7811 measured reflections	l = −22→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Only H-atom coordinates refined
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.043P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max = 0.001
2005 reflections	Δρ_max = 0.17 e Å⁻³
164 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

Crystal data top

C₁₁H₁₅NO	V = 992.3 (3) Å³
M_r = 177.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.7915 (7) Å	µ = 0.08 mm⁻¹
b = 11.593 (2) Å	T = 100 K
c = 17.966 (3) Å	0.50 × 0.14 × 0.08 mm
β = 96.11 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2005 independent reflections
Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2007); empirical (using intensity measurements) absorption correction using spherical harmonics implemented in SCALE3 ABSPACK scaling algorithm]	1262 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.989	R_int = 0.036
7811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.080	Only H-atom coordinates refined
S = 0.95	Δρ_max = 0.17 e Å⁻³
2005 reflections	Δρ_min = −0.16 e Å⁻³
164 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
O1	0.65780 (18)	0.08126 (8)	0.39277 (5)	0.0262 (3)
N1	0.2247 (2)	0.15987 (9)	0.36988 (6)	0.0189 (3)
H1N	0.044 (3)	0.1485 (11)	0.3751 (7)	0.023*
C1	0.3212 (2)	0.27503 (11)	0.36006 (6)	0.0176 (3)
C2	0.2508 (3)	0.36018 (11)	0.41017 (7)	0.0190 (3)
C3	0.3532 (3)	0.47138 (12)	0.40192 (7)	0.0227 (3)
H3	0.310 (3)	0.5309 (11)	0.4368 (7)	0.027*
C4	0.5195 (3)	0.49761 (13)	0.34589 (7)	0.0240 (3)
H4	0.592 (3)	0.5742 (12)	0.3436 (7)	0.029*
C5	0.5822 (3)	0.41284 (12)	0.29609 (7)	0.0230 (3)
H5	0.699 (3)	0.4338 (10)	0.2572 (7)	0.028*
C6	0.4831 (3)	0.30035 (11)	0.30172 (7)	0.0196 (3)
C7	0.4008 (3)	0.07132 (11)	0.38927 (7)	0.0191 (3)
C8	0.2643 (3)	−0.04089 (12)	0.40805 (8)	0.0226 (3)
H8A	0.233 (3)	−0.0348 (11)	0.4619 (8)	0.027*
H8B	0.078 (3)	−0.0457 (11)	0.3814 (7)	0.027*
C9	0.4399 (3)	−0.14537 (14)	0.39496 (10)	0.0340 (4)
H9A	0.633 (4)	−0.1371 (13)	0.4197 (8)	0.051*
H9B	0.362 (3)	−0.2172 (13)	0.4137 (8)	0.051*
H9C	0.457 (3)	−0.1568 (12)	0.3394 (9)	0.051*
C10	0.0701 (3)	0.33281 (14)	0.47103 (8)	0.0247 (4)
H10A	−0.132 (3)	0.3315 (11)	0.4530 (8)	0.037*
H10B	0.109 (3)	0.2566 (14)	0.4935 (7)	0.037*
H10C	0.096 (3)	0.3906 (12)	0.5110 (8)	0.037*
C11	0.5511 (3)	0.21070 (14)	0.24562 (8)	0.0257 (4)
H11A	0.408 (3)	0.1505 (12)	0.2393 (7)	0.039*
H11B	0.586 (3)	0.2484 (12)	0.1971 (8)	0.039*
H11C	0.726 (3)	0.1670 (11)	0.2640 (7)	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0137 (5)	0.0268 (6)	0.0384 (6)	0.0012 (4)	0.0041 (4)	0.0058 (4)
N1	0.0109 (6)	0.0207 (7)	0.0258 (6)	−0.0004 (5)	0.0047 (5)	0.0015 (5)
C1	0.0123 (7)	0.0189 (8)	0.0213 (7)	0.0010 (6)	−0.0006 (5)	0.0026 (6)
C2	0.0144 (7)	0.0225 (8)	0.0200 (7)	0.0055 (6)	0.0009 (5)	0.0025 (6)
C3	0.0219 (7)	0.0218 (9)	0.0243 (7)	0.0049 (7)	0.0022 (6)	−0.0031 (6)
C4	0.0232 (8)	0.0203 (8)	0.0285 (8)	−0.0022 (7)	0.0024 (7)	0.0029 (7)
C5	0.0211 (7)	0.0272 (9)	0.0214 (7)	−0.0004 (7)	0.0048 (6)	0.0040 (6)
C6	0.0154 (7)	0.0230 (8)	0.0199 (7)	0.0016 (6)	−0.0001 (6)	0.0006 (6)
C7	0.0163 (7)	0.0220 (8)	0.0193 (7)	0.0017 (6)	0.0030 (5)	−0.0013 (6)
C8	0.0174 (7)	0.0227 (8)	0.0281 (8)	−0.0003 (7)	0.0051 (6)	0.0015 (6)
C9	0.0236 (8)	0.0234 (9)	0.0556 (11)	0.0020 (7)	0.0068 (8)	0.0068 (8)
C10	0.0226 (8)	0.0282 (9)	0.0243 (8)	0.0021 (7)	0.0072 (6)	−0.0002 (6)
C11	0.0270 (8)	0.0284 (9)	0.0224 (7)	−0.0009 (7)	0.0065 (6)	−0.0030 (6)

Geometric parameters (Å, º) top

O1—C7	1.2317 (15)	C6—C11	1.5073 (18)
N1—C7	1.3509 (16)	C7—C8	1.5101 (18)
N1—C1	1.4299 (16)	C8—C9	1.508 (2)
N1—H1N	0.889 (14)	C8—H8A	0.998 (14)
C1—C6	1.4000 (17)	C8—H8B	0.968 (13)
C1—C2	1.4012 (17)	C9—H9A	0.988 (16)
C2—C3	1.3928 (18)	C9—H9B	0.987 (15)
C2—C10	1.4994 (19)	C9—H9C	1.020 (17)
C3—C4	1.3828 (18)	C10—H10A	0.986 (15)
C3—H3	0.969 (13)	C10—H10B	0.982 (15)
C4—C5	1.3834 (19)	C10—H10C	0.981 (14)
C4—H4	0.957 (13)	C11—H11A	0.978 (15)
C5—C6	1.3952 (18)	C11—H11B	1.005 (14)
C5—H5	0.973 (13)	C11—H11C	1.003 (15)

C7—N1—C1	122.69 (11)	C9—C8—C7	113.27 (12)
C7—N1—H1N	116.6 (8)	C9—C8—H8A	110.7 (7)
C1—N1—H1N	118.8 (8)	C7—C8—H8A	105.7 (7)
C6—C1—C2	121.59 (12)	C9—C8—H8B	112.1 (8)
C6—C1—N1	120.03 (11)	C7—C8—H8B	109.7 (8)
C2—C1—N1	118.38 (11)	H8A—C8—H8B	104.9 (11)
C3—C2—C1	118.17 (12)	C8—C9—H9A	111.4 (9)
C3—C2—C10	120.71 (12)	C8—C9—H9B	112.7 (9)
C1—C2—C10	121.11 (12)	H9A—C9—H9B	107.5 (12)
C4—C3—C2	121.19 (13)	C8—C9—H9C	111.2 (8)
C4—C3—H3	119.6 (8)	H9A—C9—H9C	106.5 (13)
C2—C3—H3	119.2 (8)	H9B—C9—H9C	107.3 (12)
C3—C4—C5	119.76 (13)	C2—C10—H10A	112.7 (8)
C3—C4—H4	118.4 (8)	C2—C10—H10B	113.0 (8)
C5—C4—H4	121.8 (8)	H10A—C10—H10B	105.1 (12)
C4—C5—C6	121.20 (13)	C2—C10—H10C	110.5 (8)
C4—C5—H5	118.0 (7)	H10A—C10—H10C	107.2 (12)
C6—C5—H5	120.8 (7)	H10B—C10—H10C	108.0 (11)
C5—C6—C1	118.05 (12)	C6—C11—H11A	111.7 (9)
C5—C6—C11	119.78 (12)	C6—C11—H11B	110.3 (8)
C1—C6—C11	122.17 (12)	H11A—C11—H11B	112.9 (11)
O1—C7—N1	122.39 (13)	C6—C11—H11C	111.1 (8)
O1—C7—C8	121.57 (12)	H11A—C11—H11C	103.2 (11)
N1—C7—C8	116.02 (11)	H11B—C11—H11C	107.3 (11)

C7—N1—C1—C6	65.81 (15)	C4—C5—C6—C1	−0.93 (19)
C7—N1—C1—C2	−113.86 (13)	C4—C5—C6—C11	178.87 (12)
C6—C1—C2—C3	−1.77 (18)	C2—C1—C6—C5	2.20 (17)
N1—C1—C2—C3	177.88 (11)	N1—C1—C6—C5	−177.45 (11)
C6—C1—C2—C10	178.15 (12)	C2—C1—C6—C11	−177.59 (12)
N1—C1—C2—C10	−2.20 (17)	N1—C1—C6—C11	2.75 (17)
C1—C2—C3—C4	0.06 (18)	C1—N1—C7—O1	−7.20 (19)
C10—C2—C3—C4	−179.86 (12)	C1—N1—C7—C8	171.64 (11)
C2—C3—C4—C5	1.17 (19)	O1—C7—C8—C9	−27.34 (19)
C3—C4—C5—C6	−0.7 (2)	N1—C7—C8—C9	153.81 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.889 (14)	2.065 (14)	2.9352 (15)	165.9 (12)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅NO
M_r	177.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	4.7915 (7), 11.593 (2), 17.966 (3)
β (°)	96.11 (2)
V (Å³)	992.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.14 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan [CrysAlis RED (Oxford Diffraction, 2007); empirical (using intensity measurements) absorption correction using spherical harmonics implemented in SCALE3 ABSPACK scaling algorithm]
T_min, T_max	0.951, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7811, 2005, 1262
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 0.95
No. of reflections	2005
No. of parameters	164
H-atom treatment	Only H-atom coordinates refined
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.889 (14)	2.065 (14)	2.9352 (15)	165.9 (12)

Symmetry code: (i) x−1, y, z.

Acknowledgements

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

References

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