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Acta Cryst. (2009). E65, o964    [ doi:10.1107/S1600536809011891 ]

N-(2,3-Dimethylphenyl)acetamide

B. T. Gowda, S. Foro, H. Terao and H. Fuess

Abstract top

The conformation of the N-H bond in the structure of the title compound, C10H13NO, is syn to both the 2- and 3-methyl substituents on the aromatic ring, and is anti to the C=O bond. N-H...O hydrogen bonds link the molecules into supramolecular chains.

Comment top

As a part of studying the ring- and side-chain substitutions on the crystal structures of chemically and biologically important class of compounds such as acetanilides (Gowda et al., 2007a,b; 2008), we report herein the crystal structure of N-(2,3-dimethylphenyl)acetamide, (I). The conformation of the C=O bond is anti to the N—H bond, Fig. 1. The conformation of the N—H bond is syn to both the 2- and 3-methyl substituents in the aromatic ring, similar to that observed with respect to to the 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2007a), but in contrast to the anti conformation observed with respect to the 2-methyl group in N-(2-methylphenyl)acetamide (Gowda et al., 2007b). The molecules in (I) are linked into supramolecular chains along the a axis through intermolecular N1—H1···O1 hydrogen bonding (Table 1) as shown in Fig. 2.

Related literature top

For preparation of the compound, see: Gowda et al. (2006). For related structures, see: Gowda et al. (2007a,b; 2008)

Experimental top

Compound (I) was prepared according to the literature method (Gowda et al., 2006) and crystals were obtained from its ethanol solution held at room temperature.

Refinement top

The N-bound H atom was located in difference map, and refined with N—H = 0.85 (3) Å. The remaining H atoms were positioned with in their idealized geometry using a riding model with C—H = 0.93–0.96 Å, and with Uiso(H) set to 1.2 x Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); 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, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N-(2,3-Dimethylphenyl)acetamide top
Crystal data top
C10H13NOF(000) = 352
Mr = 163.21Dx = 1.186 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2448 reflections
a = 4.7961 (5) Åθ = 2.6–27.6°
b = 12.385 (1) ŵ = 0.08 mm−1
c = 15.475 (2) ÅT = 299 K
β = 96.23 (1)°Needle, colourless
V = 913.78 (17) Å30.45 × 0.08 × 0.04 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		1660 independent reflections
Radiation source: fine-focus sealed tube1121 reflections with I > 2σ(I)
graphiteRint = 0.035
Rotation method data acquisition using ω and phi scans.θmax = 25.3°, θmin = 2.7°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		h = −3→5
Tmin = 0.967, Tmax = 0.993k = −14→13
5890 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.26 w = 1/[σ2(Fo2) + (0.0286P)2 + 0.8009P]
where P = (Fo2 + 2Fc2)/3
1660 reflections(Δ/σ)max = 0.001
115 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C10H13NOV = 913.78 (17) Å3
Mr = 163.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.7961 (5) ŵ = 0.08 mm−1
b = 12.385 (1) ÅT = 299 K
c = 15.475 (2) Å0.45 × 0.08 × 0.04 mm
β = 96.23 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		1660 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		1121 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.993Rint = 0.035
5890 measured reflectionsθmax = 25.3°
Refinement top
R[F2 > 2σ(F2)] = 0.073H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156Δρmax = 0.23 e Å−3
S = 1.26Δρmin = −0.18 e Å−3
1660 reflectionsAbsolute structure: ?
115 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. Absorption correction details: CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/Ueq
C1−0.0442 (6)0.9157 (3)0.87038 (19)0.0414 (8)
C20.0495 (6)0.9258 (3)0.7884 (2)0.0424 (8)
C3−0.0385 (6)1.0149 (3)0.7370 (2)0.0502 (9)
C4−0.2211 (7)1.0883 (3)0.7678 (3)0.0620 (10)
H4−0.28111.14730.73350.074*
C5−0.3162 (7)1.0761 (3)0.8479 (3)0.0639 (11)
H5−0.44131.12600.86680.077*
C6−0.2269 (6)0.9905 (3)0.9001 (2)0.0521 (9)
H6−0.28810.98280.95480.063*
C7−0.1038 (6)0.7664 (3)0.9715 (2)0.0468 (8)
C80.0486 (7)0.6820 (3)1.0266 (2)0.0606 (10)
H8A0.03830.69841.08680.073*
H8B0.24140.68031.01530.073*
H8C−0.03570.61281.01320.073*
C90.2419 (7)0.8429 (3)0.7556 (2)0.0523 (9)
H9A0.25240.78110.79320.063*
H9B0.42560.87340.75480.063*
H9C0.17030.82140.69780.063*
C100.0608 (8)1.0314 (3)0.6489 (2)0.0690 (11)
H10A−0.00290.97260.61140.083*
H10B0.26201.03410.65470.083*
H10C−0.01341.09800.62440.083*
N10.0539 (5)0.8282 (2)0.92501 (16)0.0432 (7)
H1N0.230 (7)0.818 (3)0.931 (2)0.052*
O1−0.3582 (4)0.7763 (2)0.96925 (18)0.0722 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0283 (15)0.045 (2)0.0503 (19)0.0009 (14)−0.0004 (13)−0.0039 (15)
C20.0317 (16)0.045 (2)0.0497 (19)−0.0051 (14)0.0012 (13)−0.0040 (15)
C30.0429 (18)0.047 (2)0.058 (2)−0.0068 (16)−0.0060 (15)0.0043 (17)
C40.054 (2)0.046 (2)0.082 (3)0.0039 (18)−0.010 (2)0.008 (2)
C50.050 (2)0.057 (3)0.083 (3)0.0135 (18)−0.0006 (19)−0.012 (2)
C60.0428 (18)0.057 (2)0.056 (2)0.0048 (17)0.0034 (15)−0.0088 (18)
C70.0351 (18)0.056 (2)0.0500 (19)−0.0013 (16)0.0092 (14)−0.0032 (17)
C80.048 (2)0.071 (3)0.065 (2)−0.0048 (18)0.0144 (17)0.015 (2)
C90.0497 (19)0.059 (2)0.0499 (19)0.0009 (17)0.0121 (15)0.0004 (17)
C100.074 (3)0.071 (3)0.060 (2)−0.009 (2)−0.0039 (19)0.014 (2)
N10.0272 (13)0.0530 (17)0.0504 (15)0.0043 (13)0.0084 (12)0.0046 (14)
O10.0289 (12)0.085 (2)0.104 (2)0.0005 (12)0.0148 (12)0.0147 (16)
Geometric parameters (Å, °) top
C1—C61.388 (4)C7—N11.339 (4)
C1—C21.396 (4)C7—C81.490 (5)
C1—N11.423 (4)C8—H8A0.9600
C2—C31.399 (4)C8—H8B0.9600
C2—C91.504 (4)C8—H8C0.9600
C3—C41.382 (5)C9—H9A0.9600
C3—C101.506 (5)C9—H9B0.9600
C4—C51.374 (5)C9—H9C0.9600
C4—H40.9300C10—H10A0.9600
C5—C61.373 (5)C10—H10B0.9600
C5—H50.9300C10—H10C0.9600
C6—H60.9300N1—H1N0.85 (3)
C7—O11.223 (3)
C6—C1—C2121.2 (3)C7—C8—H8A109.5
C6—C1—N1119.5 (3)C7—C8—H8B109.5
C2—C1—N1119.3 (3)H8A—C8—H8B109.5
C1—C2—C3118.7 (3)C7—C8—H8C109.5
C1—C2—C9121.0 (3)H8A—C8—H8C109.5
C3—C2—C9120.3 (3)H8B—C8—H8C109.5
C4—C3—C2119.1 (3)C2—C9—H9A109.5
C4—C3—C10119.8 (3)C2—C9—H9B109.5
C2—C3—C10121.1 (3)H9A—C9—H9B109.5
C5—C4—C3121.6 (3)C2—C9—H9C109.5
C5—C4—H4119.2H9A—C9—H9C109.5
C3—C4—H4119.2H9B—C9—H9C109.5
C6—C5—C4120.2 (3)C3—C10—H10A109.5
C6—C5—H5119.9C3—C10—H10B109.5
C4—C5—H5119.9H10A—C10—H10B109.5
C5—C6—C1119.3 (3)C3—C10—H10C109.5
C5—C6—H6120.4H10A—C10—H10C109.5
C1—C6—H6120.4H10B—C10—H10C109.5
O1—C7—N1123.2 (3)C7—N1—C1125.8 (3)
O1—C7—C8120.9 (3)C7—N1—H1N117 (2)
N1—C7—C8116.0 (3)C1—N1—H1N117 (2)
C6—C1—C2—C31.7 (4)C10—C3—C4—C5−179.9 (3)
N1—C1—C2—C3−177.1 (3)C3—C4—C5—C61.0 (5)
C6—C1—C2—C9−178.5 (3)C4—C5—C6—C1−1.2 (5)
N1—C1—C2—C92.8 (4)C2—C1—C6—C5−0.2 (5)
C1—C2—C3—C4−1.8 (4)N1—C1—C6—C5178.6 (3)
C9—C2—C3—C4178.3 (3)O1—C7—N1—C13.0 (5)
C1—C2—C3—C10178.6 (3)C8—C7—N1—C1−177.8 (3)
C9—C2—C3—C10−1.2 (5)C6—C1—N1—C745.2 (4)
C2—C3—C4—C50.5 (5)C2—C1—N1—C7−136.0 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (3)2.06 (3)2.901 (3)169 (3)
Symmetry codes: (i) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (3)2.06 (3)2.901 (3)169 (3)
Symmetry codes: (i) x+1, y, z.
references
References top

Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2631–o2632.

Gowda, B. T., Foro, S. & Fuess, H. (2008). Acta Cryst. E64, o11.

Gowda, B. T., Kožíšek, J., Tokarčík, M. & Fuess, H. (2007b). Acta Cryst. E63, o1977–o1978.

Gowda, B. T., Shilpa & Lakshmipathy, J. K. (2006). Z. Naturforsch. Teil A, 61, 595–599.

Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.

Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.