2-Chloro-N-(2,6-dimethyl­phen­yl)acetamide

Gowda, B.T.; Foro, S.; Svoboda, I.; Paulus, H.; Fuess, H.

doi:10.1107/S160053680706624X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o286

https://doi.org/10.1107/S160053680706624X

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2-Chloro-N-(2,6-dimethylphenyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b Ingrid Svoboda,^b Helmut Paulus ^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 November 2007; accepted 8 December 2007; online 18 December 2007)

The crystal structure of the title compound (26DMPCA), C₁₀H₁₂ClNO, is closely related to those of side-chain-unsubstituted N-(2,6-dimethylphenyl)acetamide and side-chain-substituted 2,2,2-trichloro-N-(2,6-dimethylphenyl)acetamide and N-(2,6-dimethylphenyl)-2,2,2-trimethylacetamide, with slightly different bond parameters. The molecules in 26DMPCA are linked into chains through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2004 , 2007a ,b ,c ,d ,e ,f ); Gowda, Kozisek et al. (2007 ); Gowda, Svoboda & Fuess (2007 ).

Experimental

Crystal data

C₁₀H₁₂ClNO
M_r = 197.66
Monoclinic, P 2₁ /c
a = 13.766 (3) Å
b = 8.911 (2) Å
c = 8.538 (2) Å
β = 99.00 (1)°
V = 1034.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 300 (2) K
0.50 × 0.15 × 0.12 mm

Data collection

Stoe Stadi-4 diffractometer
Absorption correction: numerical (North et al., 1968 ) T_min = 0.952, T_max = 0.968
1318 measured reflections
1188 independent reflections
1053 reflections with I > 2σ(I)
R_int = 0.015
θ_max = 22.5°
3 standard reflections frequency: 200 min intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.10
1188 reflections
123 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯O4ⁱ	0.86 (3)	2.04 (3)	2.866 (3)	161 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: STADI4 (Stoe & Cie, 1987 ); cell refinement: STADI4; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680706624X/lw2052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706624X/lw2052Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(2,6-dimethylphenyl)- acetamide (26DMPCA) has been determined as part of a study of the effect of ring and side chain substitutions on the solid state geometry of chemically and biologically significant compounds such as acetanilides (Gowda et al., 2007a, 2007b, 2007c, 2007d, 2007e). The structure of 26DMPCA is closely related to the side chain unsubstituted N-(2,6-dimethylphenyl)-acetamide (26DMPA) (Gowda et al., 2007c) and side chain substituted, 2,2,2-trichloro-N-(2,6-dimethylphenyl)-acetamide (26DMPTCA) (Gowda et al., 2007b) and 2,2,2-trimethyl-N- (2,6-dimethylphenyl)-acetamide (26DMPTMA) (Gowda et al., 2007d). The bond parameters in 26DMPCA are similar to those in 26DMPA, 26DMPTCA, 26DMPTMA and other acetanilides (Gowda et al., 2007a, 2007b, 2007c, 2007d, 2007e). The molecules in 26DMPcA 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, 2007a,b,c,d,e,f); Gowda, Kozisek et al. (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.

Structure description top

For related literature, see: Gowda et al. (2004, 2007a,b,c,d,e,f); Gowda, Kozisek et al. (2007); Gowda, Svoboda & Fuess (2007).

Computing details top

Data collection: STADI4 (Stoe & Cie, 1987); cell refinement: STADI4 (Stoe & Cie, 1987); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); 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. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

2-Chloro-N-(2,6-dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₂ClNO	F(000) = 416
M_r = 197.66	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 40 reflections
a = 13.766 (3) Å	θ = 18.0–20.9°
b = 8.911 (2) Å	µ = 0.33 mm⁻¹
c = 8.538 (2) Å	T = 300 K
β = 99.00 (1)°	Needle, colourless
V = 1034.4 (4) Å³	0.50 × 0.15 × 0.12 mm
Z = 4

Data collection top

Stoe Stadi-4 diffractometer	1053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 22.5°, θ_min = 2.7°
Profile fitted scans 2θ/ω=1/1	h = −14→14
Absorption correction: numerical (North et al., 1968)	k = 0→9
T_min = 0.952, T_max = 0.968	l = 0→9
1318 measured reflections	3 standard reflections every 200 min
1188 independent reflections	intensity decay: 2%

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0457P)² + 0.4775P] where P = (F_o² + 2F_c²)/3
1188 reflections	(Δ/σ)_max < 0.001
123 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₁₂ClNO	V = 1034.4 (4) Å³
M_r = 197.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.766 (3) Å	µ = 0.33 mm⁻¹
b = 8.911 (2) Å	T = 300 K
c = 8.538 (2) Å	0.50 × 0.15 × 0.12 mm
β = 99.00 (1)°

Data collection top

Stoe Stadi-4 diffractometer	1053 reflections with I > 2σ(I)
Absorption correction: numerical (North et al., 1968)	R_int = 0.015
T_min = 0.952, T_max = 0.968	θ_max = 22.5°
1318 measured reflections	3 standard reflections every 200 min
1188 independent reflections	intensity decay: 2%

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.18 e Å⁻³
1188 reflections	Δρ_min = −0.20 e Å⁻³
123 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
Cl1	0.57659 (6)	0.28510 (10)	0.14255 (11)	0.0828 (3)
C2	0.49079 (17)	0.1523 (3)	0.1922 (3)	0.0513 (6)
H2A	0.5164	0.0516	0.1845	0.062*
H2B	0.4798	0.1684	0.3005	0.062*
C3	0.39513 (17)	0.1690 (3)	0.0802 (3)	0.0429 (6)
O4	0.39022 (12)	0.1400 (2)	−0.06122 (19)	0.0558 (5)
N5	0.31738 (15)	0.2133 (2)	0.1451 (3)	0.0453 (5)
H5N	0.327 (2)	0.249 (3)	0.240 (4)	0.054*
C6	0.22271 (18)	0.2355 (3)	0.0519 (3)	0.0427 (6)
C7	0.19078 (19)	0.3809 (3)	0.0168 (3)	0.0523 (6)
C8	0.0989 (2)	0.3999 (3)	−0.0760 (3)	0.0649 (8)
H8	0.0753	0.4963	−0.1002	0.078*
C9	0.0431 (2)	0.2789 (4)	−0.1320 (4)	0.0708 (9)
H9	−0.0176	0.2935	−0.1952	0.085*
C10	0.0758 (2)	0.1364 (4)	−0.0957 (3)	0.0646 (8)
H10	0.0369	0.0552	−0.1342	0.077*
C11	0.16630 (19)	0.1110 (3)	−0.0023 (3)	0.0520 (6)
C12	0.2526 (2)	0.5139 (3)	0.0770 (4)	0.0811 (9)
H12A	0.2218	0.6041	0.0322	0.097*
H12B	0.3166	0.5044	0.0468	0.097*
H12C	0.2588	0.5181	0.1905	0.097*
C13	0.2003 (2)	−0.0464 (3)	0.0398 (4)	0.0719 (8)
H13A	0.2543	−0.0711	−0.0143	0.086*
H13B	0.1471	−0.1152	0.0083	0.086*
H13C	0.2211	−0.0536	0.1522	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0568 (5)	0.1009 (7)	0.0869 (6)	−0.0204 (4)	−0.0005 (4)	0.0113 (4)
C2	0.0438 (13)	0.0629 (16)	0.0463 (13)	0.0064 (12)	0.0042 (11)	0.0048 (11)
C3	0.0452 (14)	0.0458 (14)	0.0374 (14)	0.0021 (11)	0.0058 (10)	0.0056 (10)
O4	0.0506 (10)	0.0790 (13)	0.0375 (10)	0.0091 (9)	0.0060 (7)	−0.0012 (8)
N5	0.0404 (12)	0.0594 (13)	0.0347 (10)	0.0028 (9)	0.0016 (9)	−0.0026 (9)
C6	0.0374 (14)	0.0539 (15)	0.0372 (11)	0.0012 (11)	0.0073 (11)	0.0023 (10)
C7	0.0493 (15)	0.0548 (15)	0.0522 (14)	0.0009 (12)	0.0062 (12)	0.0040 (12)
C8	0.0547 (17)	0.0666 (18)	0.0711 (17)	0.0146 (14)	0.0022 (14)	0.0140 (15)
C9	0.0447 (17)	0.094 (2)	0.0687 (18)	0.0043 (16)	−0.0070 (15)	0.0096 (16)
C10	0.0479 (16)	0.076 (2)	0.0657 (17)	−0.0097 (14)	−0.0029 (14)	−0.0065 (14)
C11	0.0483 (15)	0.0563 (15)	0.0505 (13)	−0.0007 (12)	0.0053 (12)	−0.0026 (12)
C12	0.085 (2)	0.0578 (18)	0.096 (2)	−0.0039 (16)	−0.0008 (18)	0.0036 (16)
C13	0.0662 (19)	0.0567 (17)	0.091 (2)	−0.0056 (14)	0.0051 (16)	−0.0014 (15)

Geometric parameters (Å, º) top

Cl1—C2	1.770 (3)	C8—H8	0.9300
C2—C3	1.509 (3)	C9—C10	1.366 (4)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—C11	1.389 (4)
C3—O4	1.227 (3)	C10—H10	0.9300
C3—N5	1.339 (3)	C11—C13	1.505 (4)
N5—C6	1.431 (3)	C12—H12A	0.9600
N5—H5N	0.86 (3)	C12—H12B	0.9600
C6—C7	1.386 (3)	C12—H12C	0.9600
C6—C11	1.391 (3)	C13—H13A	0.9600
C7—C8	1.394 (4)	C13—H13B	0.9600
C7—C12	1.501 (4)	C13—H13C	0.9600
C8—C9	1.367 (4)

C3—C2—Cl1	109.33 (17)	C10—C9—C8	120.4 (3)
C3—C2—H2A	109.8	C10—C9—H9	119.8
Cl1—C2—H2A	109.8	C8—C9—H9	119.8
C3—C2—H2B	109.8	C9—C10—C11	121.1 (3)
Cl1—C2—H2B	109.8	C9—C10—H10	119.5
H2A—C2—H2B	108.3	C11—C10—H10	119.5
O4—C3—N5	123.0 (2)	C10—C11—C6	117.7 (2)
O4—C3—C2	120.8 (2)	C10—C11—C13	120.4 (2)
N5—C3—C2	116.2 (2)	C6—C11—C13	121.9 (2)
C3—N5—C6	121.9 (2)	C7—C12—H12A	109.5
C3—N5—H5N	119 (2)	C7—C12—H12B	109.5
C6—N5—H5N	117.6 (19)	H12A—C12—H12B	109.5
C7—C6—C11	122.1 (2)	C7—C12—H12C	109.5
C7—C6—N5	118.7 (2)	H12A—C12—H12C	109.5
C11—C6—N5	119.2 (2)	H12B—C12—H12C	109.5
C6—C7—C8	117.7 (2)	C11—C13—H13A	109.5
C6—C7—C12	121.3 (2)	C11—C13—H13B	109.5
C8—C7—C12	120.9 (3)	H13A—C13—H13B	109.5
C9—C8—C7	120.9 (3)	C11—C13—H13C	109.5
C9—C8—H8	119.5	H13A—C13—H13C	109.5
C7—C8—H8	119.5	H13B—C13—H13C	109.5

Cl1—C2—C3—O4	66.1 (3)	C6—C7—C8—C9	−0.9 (4)
Cl1—C2—C3—N5	−115.4 (2)	C12—C7—C8—C9	179.4 (3)
O4—C3—N5—C6	−2.4 (4)	C7—C8—C9—C10	1.0 (5)
C2—C3—N5—C6	179.1 (2)	C8—C9—C10—C11	−0.3 (5)
C3—N5—C6—C7	−103.9 (3)	C9—C10—C11—C6	−0.5 (4)
C3—N5—C6—C11	75.3 (3)	C9—C10—C11—C13	178.5 (3)
C11—C6—C7—C8	0.0 (4)	C7—C6—C11—C10	0.7 (4)
N5—C6—C7—C8	179.2 (2)	N5—C6—C11—C10	−178.5 (2)
C11—C6—C7—C12	179.7 (3)	C7—C6—C11—C13	−178.4 (3)
N5—C6—C7—C12	−1.1 (4)	N5—C6—C11—C13	2.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O4ⁱ	0.86 (3)	2.04 (3)	2.866 (3)	161 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂ClNO
M_r	197.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	13.766 (3), 8.911 (2), 8.538 (2)
β (°)	99.00 (1)
V (Å³)	1034.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.50 × 0.15 × 0.12

Data collection
Diffractometer	Stoe Stadi-4 diffractometer
Absorption correction	Numerical (North et al., 1968)
T_min, T_max	0.952, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	1318, 1188, 1053
R_int	0.015
θ_max (°)	22.5
(sin θ/λ)_max (Å⁻¹)	0.538

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.10
No. of reflections	1188
No. of parameters	123
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: STADI4 (Stoe & Cie, 1987), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O4ⁱ	0.86 (3)	2.04 (3)	2.866 (3)	161 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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

References

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