N-(2,3-Dimethyl­phen­yl)acetamide

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

doi:10.1107/S1600536809011891

organic compounds

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Volume 65| Part 5| May 2009| Page o964

doi:10.1107/S1600536809011891

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N-(2,3-Dimethylphenyl)acetamide

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 30 March 2009; accepted 31 March 2009; online 8 April 2009)

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.

Related literature

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

Experimental

Crystal data

C₁₀H₁₃NO
M_r = 163.21
Monoclinic, P 2₁ /n
a = 4.7961 (5) Å
b = 12.385 (1) Å
c = 15.475 (2) Å
β = 96.23 (1)°
V = 913.78 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 299 K
0.45 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.967, T_max = 0.993
5890 measured reflections
1660 independent reflections
1121 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.156
S = 1.26
1660 reflections
115 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.85 (3)	2.06 (3)	2.901 (3)	169 (3)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); 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, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011891/tk2409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011891/tk2409Isup2.hkl

checkCIF report

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.

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

	Fig. 1. Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N-(2,3-Dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₃NO	F(000) = 352
M_r = 163.21	D_x = 1.186 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2448 reflections
a = 4.7961 (5) Å	θ = 2.6–27.6°
b = 12.385 (1) Å	µ = 0.08 mm⁻¹
c = 15.475 (2) Å	T = 299 K
β = 96.23 (1)°	Needle, colourless
V = 913.78 (17) Å³	0.45 × 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 tube	1121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Rotation method data acquisition using ω and phi scans.	θ_max = 25.3°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −3→5
T_min = 0.967, T_max = 0.993	k = −14→13
5890 measured reflections	l = −18→18

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ²(F_o²) + (0.0286P)² + 0.8009P] where P = (F_o² + 2F_c²)/3
1660 reflections	(Δ/σ)_max = 0.001
115 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₁₃NO	V = 913.78 (17) Å³
M_r = 163.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.7961 (5) Å	µ = 0.08 mm⁻¹
b = 12.385 (1) Å	T = 299 K
c = 15.475 (2) Å	0.45 × 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)
T_min = 0.967, T_max = 0.993	R_int = 0.035
5890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	Δρ_max = 0.23 e Å⁻³
1660 reflections	Δρ_min = −0.18 e Å⁻³
115 parameters

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

	x	y	z	U_iso*/U_eq
C1	−0.0442 (6)	0.9157 (3)	0.87038 (19)	0.0414 (8)
C2	0.0495 (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	−0.2811	1.1473	0.7335	0.074*
C5	−0.3162 (7)	1.0761 (3)	0.8479 (3)	0.0639 (11)
H5	−0.4413	1.1260	0.8668	0.077*
C6	−0.2269 (6)	0.9905 (3)	0.9001 (2)	0.0521 (9)
H6	−0.2881	0.9828	0.9548	0.063*
C7	−0.1038 (6)	0.7664 (3)	0.9715 (2)	0.0468 (8)
C8	0.0486 (7)	0.6820 (3)	1.0266 (2)	0.0606 (10)
H8A	0.0383	0.6984	1.0868	0.073*
H8B	0.2414	0.6803	1.0153	0.073*
H8C	−0.0357	0.6128	1.0132	0.073*
C9	0.2419 (7)	0.8429 (3)	0.7556 (2)	0.0523 (9)
H9A	0.2524	0.7811	0.7932	0.063*
H9B	0.4256	0.8734	0.7548	0.063*
H9C	0.1703	0.8214	0.6978	0.063*
C10	0.0608 (8)	1.0314 (3)	0.6489 (2)	0.0690 (11)
H10A	−0.0029	0.9726	0.6114	0.083*
H10B	0.2620	1.0341	0.6547	0.083*
H10C	−0.0134	1.0980	0.6244	0.083*
N1	0.0539 (5)	0.8282 (2)	0.92501 (16)	0.0432 (7)
H1N	0.230 (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

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0283 (15)	0.045 (2)	0.0503 (19)	0.0009 (14)	−0.0004 (13)	−0.0039 (15)
C2	0.0317 (16)	0.045 (2)	0.0497 (19)	−0.0051 (14)	0.0012 (13)	−0.0040 (15)
C3	0.0429 (18)	0.047 (2)	0.058 (2)	−0.0068 (16)	−0.0060 (15)	0.0043 (17)
C4	0.054 (2)	0.046 (2)	0.082 (3)	0.0039 (18)	−0.010 (2)	0.008 (2)
C5	0.050 (2)	0.057 (3)	0.083 (3)	0.0135 (18)	−0.0006 (19)	−0.012 (2)
C6	0.0428 (18)	0.057 (2)	0.056 (2)	0.0048 (17)	0.0034 (15)	−0.0088 (18)
C7	0.0351 (18)	0.056 (2)	0.0500 (19)	−0.0013 (16)	0.0092 (14)	−0.0032 (17)
C8	0.048 (2)	0.071 (3)	0.065 (2)	−0.0048 (18)	0.0144 (17)	0.015 (2)
C9	0.0497 (19)	0.059 (2)	0.0499 (19)	0.0009 (17)	0.0121 (15)	0.0004 (17)
C10	0.074 (3)	0.071 (3)	0.060 (2)	−0.009 (2)	−0.0039 (19)	0.014 (2)
N1	0.0272 (13)	0.0530 (17)	0.0504 (15)	0.0043 (13)	0.0084 (12)	0.0046 (14)
O1	0.0289 (12)	0.085 (2)	0.104 (2)	0.0005 (12)	0.0148 (12)	0.0147 (16)

Geometric parameters (Å, º) top

C1—C6	1.388 (4)	C7—N1	1.339 (4)
C1—C2	1.396 (4)	C7—C8	1.490 (5)
C1—N1	1.423 (4)	C8—H8A	0.9600
C2—C3	1.399 (4)	C8—H8B	0.9600
C2—C9	1.504 (4)	C8—H8C	0.9600
C3—C4	1.382 (5)	C9—H9A	0.9600
C3—C10	1.506 (5)	C9—H9B	0.9600
C4—C5	1.374 (5)	C9—H9C	0.9600
C4—H4	0.9300	C10—H10A	0.9600
C5—C6	1.373 (5)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—H6	0.9300	N1—H1N	0.85 (3)
C7—O1	1.223 (3)

C6—C1—C2	121.2 (3)	C7—C8—H8A	109.5
C6—C1—N1	119.5 (3)	C7—C8—H8B	109.5
C2—C1—N1	119.3 (3)	H8A—C8—H8B	109.5
C1—C2—C3	118.7 (3)	C7—C8—H8C	109.5
C1—C2—C9	121.0 (3)	H8A—C8—H8C	109.5
C3—C2—C9	120.3 (3)	H8B—C8—H8C	109.5
C4—C3—C2	119.1 (3)	C2—C9—H9A	109.5
C4—C3—C10	119.8 (3)	C2—C9—H9B	109.5
C2—C3—C10	121.1 (3)	H9A—C9—H9B	109.5
C5—C4—C3	121.6 (3)	C2—C9—H9C	109.5
C5—C4—H4	119.2	H9A—C9—H9C	109.5
C3—C4—H4	119.2	H9B—C9—H9C	109.5
C6—C5—C4	120.2 (3)	C3—C10—H10A	109.5
C6—C5—H5	119.9	C3—C10—H10B	109.5
C4—C5—H5	119.9	H10A—C10—H10B	109.5
C5—C6—C1	119.3 (3)	C3—C10—H10C	109.5
C5—C6—H6	120.4	H10A—C10—H10C	109.5
C1—C6—H6	120.4	H10B—C10—H10C	109.5
O1—C7—N1	123.2 (3)	C7—N1—C1	125.8 (3)
O1—C7—C8	120.9 (3)	C7—N1—H1N	117 (2)
N1—C7—C8	116.0 (3)	C1—N1—H1N	117 (2)

C6—C1—C2—C3	1.7 (4)	C10—C3—C4—C5	−179.9 (3)
N1—C1—C2—C3	−177.1 (3)	C3—C4—C5—C6	1.0 (5)
C6—C1—C2—C9	−178.5 (3)	C4—C5—C6—C1	−1.2 (5)
N1—C1—C2—C9	2.8 (4)	C2—C1—C6—C5	−0.2 (5)
C1—C2—C3—C4	−1.8 (4)	N1—C1—C6—C5	178.6 (3)
C9—C2—C3—C4	178.3 (3)	O1—C7—N1—C1	3.0 (5)
C1—C2—C3—C10	178.6 (3)	C8—C7—N1—C1	−177.8 (3)
C9—C2—C3—C10	−1.2 (5)	C6—C1—N1—C7	45.2 (4)
C2—C3—C4—C5	0.5 (5)	C2—C1—N1—C7	−136.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (3)	2.06 (3)	2.901 (3)	169 (3)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO
M_r	163.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	4.7961 (5), 12.385 (1), 15.475 (2)
β (°)	96.23 (1)
V (Å³)	913.78 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.08 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.967, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5890, 1660, 1121
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.156, 1.26
No. of reflections	1660
No. of parameters	115
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (3)	2.06 (3)	2.901 (3)	169 (3)

Symmetry code: (i) x+1, y, z.

References

Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2631–o2632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2008). Acta Cryst. E64, o11. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Kožíšek, J., Tokarčík, M. & Fuess, H. (2007b). Acta Cryst. E63, o1977–o1978. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Shilpa & Lakshmipathy, J. K. (2006). Z. Naturforsch. Teil A, 61, 595–599. CAS Google Scholar
Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany. Google Scholar
Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o964

doi:10.1107/S1600536809011891

Open

access