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

Abstract

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,

• a = 4.7915 (7) Å

• b = 11.593 (2) Å

• c = 17.966 (3) Å

• β = 96.11 (2)°

• V = 992.3 (3) ų

• 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 ▶)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[F ² > 2σ(F ²)] = 0.033

• wR(F ²) = 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

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

The H atoms were located in difference map, and their positional parameters were refined freely with N—H = 0.89 (1) %A and C—H = 0.96 (1)–1.02 (2) Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U_eq of the parent atom).

Figures

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.

Crystal data

C11H15NO	F000 = 384
Mr = 177.24	Dx = 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 = 2.1–24.9º
b = 11.593 (2) Å	µ = 0.08 mm−1
c = 17.966 (3) Å	T = 100 (2) K
β = 96.11 (2)º	Needle, colourless
V = 992.3 (3) Å3	0.50 × 0.14 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2005 independent reflections
Radiation source: fine-focus sealed tube	1262 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
T = 100(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.9º
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
Tmin = 0.951, Tmax = 0.989	k = −13→14
7811 measured reflections	l = −22→21

Refinement

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	Only H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.043P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080	(Δ/σ)max = 0.001
S = 0.95	Δρmax = 0.17 e Å−3
2005 reflections	Δρmin = −0.16 e Å−3
164 parameters	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)
Secondary atom site location: difference Fourier map

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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 codes: (i) x−1, y, z.