2-Chloro-N-(2,4-dimethyl­phen­yl)acetamide

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

doi:10.1107/S1600536807062563

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o85

https://doi.org/10.1107/S1600536807062563

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2-Chloro-N-(2,4-dimethylphenyl)acetamide

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 22 November 2007; accepted 23 November 2007; online 6 December 2007)

The conformation of the N—H bond in the structure of the title compound, C₁₀H₁₂ClNO, is syn to the ortho methyl group, similar to that observed with respect to the meta methyl group in 2-chloro-N-(3-methylphenyl)acetamide and the ortho-chloro group in 2-chloro-N-(2-chlorophenyl)acetamide. The geometric parameters are similar to those of other acetanilides. The molecules are linked into chains through intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2007a ,b ,c ,d ,e ,f , 2008 ); Shilpa & Gowda (2007 ).

Experimental

Crystal data

C₁₀H₁₂ClNO
M_r = 197.66
Triclinic, $[P \overline 1]$
a = 4.7235 (7) Å
b = 10.407 (2) Å
c = 11.451 (2) Å
α = 67.07 (2)°
β = 86.84 (1)°
γ = 78.95 (2)°
V = 508.69 (15) Å³
Z = 2
Cu Kα radiation
μ = 3.00 mm⁻¹
T = 299 (2) K
0.60 × 0.06 × 0.04 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.803, T_max = 0.895
2059 measured reflections
1817 independent reflections
1394 reflections with I > 2σ(I)
R_int = 0.015
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.190
S = 1.09
1817 reflections
123 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.83 (4)	2.04 (4)	2.853 (3)	165 (3)
Symmetry code: (i) x+1, y, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; 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/S1600536807062563/bt2650sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062563/bt2650Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(2,4-dimethylphenyl)- acetamide (24DMPCA) has been determined as part of a study of the effect of ring and side chain substitutions on the solid state geometry of aromatic amides (Gowda et al., 2007a, b, c, d, e). The conformation of the N—H bond in the structure of 24DMPCA is syn to the ortho methyl group (Fig. 1), similar to that observed with respect to the meta methyl group in the 2-chloro- N-(3-methylphenyl)acetamide (3MPCA)(Gowda et al., 2007e). and ortho chloro group in the 2-chloro-N-(2-chlorophenyl)- acetamide(2CPCA)(Gowda et al., 2007d). The geometric parameters in 24DMPCA are similar to those in 3MPCA (Gowda et al., 2007e), 2CPCA (Gowda et al., 2007d), 2-chloro-N-(4-methylphenyl)- acetamide (Gowda et al., 2007b), 2-chloro-N- (4-chlorophenyl)-acetamide (Gowda et al., 2007c) and other acetanilides (Gowda et al. , 2007a). The molecules in the structure are linked into chains through intermolecular N—H···O hydrogen bonding (Table 1 and Fig.2).

Related literature top

For related literature, see: Gowda et al. (2007a, 2007b, 2007c, 2007d, 2007e, 2007f), 2008); Shilpa & Gowda (2007).

Experimental top

The title compound was prepared according to the literature method (Shilpa and Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Shilpa and Gowda, 2007). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Structure description top

For related literature, see: Gowda et al. (2007a, 2007b, 2007c, 2007d, 2007e, 2007f), 2008); Shilpa & Gowda (2007).

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); 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-(2,4-dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₂ClNO	Z = 2
M_r = 197.66	F(000) = 208
Triclinic, P1	D_x = 1.290 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 4.7235 (7) Å	Cell parameters from 25 reflections
b = 10.407 (2) Å	θ = 4.2–26.4°
c = 11.451 (2) Å	µ = 3.00 mm⁻¹
α = 67.07 (2)°	T = 299 K
β = 86.84 (1)°	Needle, colourless
γ = 78.95 (2)°	0.60 × 0.06 × 0.04 mm
V = 508.69 (15) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1394 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 66.9°, θ_min = 4.2°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan North et al. (1968)	k = −12→12
T_min = 0.803, T_max = 0.895	l = −13→13
2059 measured reflections	3 standard reflections every 120 min
1817 independent reflections	intensity decay: 1.0%

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.1035P)² + 0.2646P] where P = (F_o² + 2F_c²)/3
1817 reflections	(Δ/σ)_max = 0.044
123 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₀H₁₂ClNO	γ = 78.95 (2)°
M_r = 197.66	V = 508.69 (15) Å³
Triclinic, P1	Z = 2
a = 4.7235 (7) Å	Cu Kα radiation
b = 10.407 (2) Å	µ = 3.00 mm⁻¹
c = 11.451 (2) Å	T = 299 K
α = 67.07 (2)°	0.60 × 0.06 × 0.04 mm
β = 86.84 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1394 reflections with I > 2σ(I)
Absorption correction: ψ scan North et al. (1968)	R_int = 0.015
T_min = 0.803, T_max = 0.895	3 standard reflections every 120 min
2059 measured reflections	intensity decay: 1.0%
1817 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.45 e Å⁻³
1817 reflections	Δρ_min = −0.47 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	0.5208 (2)	−0.02640 (14)	0.75189 (11)	0.1062 (6)
O1	0.2611 (4)	0.1946 (3)	0.5165 (2)	0.0695 (8)
N1	0.6642 (5)	0.2847 (3)	0.4451 (2)	0.0411 (6)
H1N	0.842 (8)	0.271 (3)	0.453 (3)	0.049*
C1	0.5306 (5)	0.4140 (3)	0.3481 (3)	0.0380 (6)
C2	0.6351 (5)	0.4545 (3)	0.2256 (3)	0.0426 (7)
C3	0.5019 (7)	0.5837 (3)	0.1357 (3)	0.0520 (8)
H3	0.5711	0.6130	0.0536	0.062*
C4	0.2697 (7)	0.6709 (3)	0.1634 (3)	0.0539 (8)
C5	0.1706 (7)	0.6261 (3)	0.2857 (3)	0.0536 (8)
H5	0.0142	0.6822	0.3062	0.064*
C6	0.2985 (6)	0.5003 (3)	0.3774 (3)	0.0461 (7)
H6	0.2300	0.4724	0.4597	0.055*
C7	0.5218 (5)	0.1865 (3)	0.5227 (3)	0.0449 (7)
C8	0.7104 (6)	0.0592 (4)	0.6200 (3)	0.0590 (9)
H8A	0.8681	0.0901	0.6462	0.071*
H8B	0.7927	−0.0072	0.5812	0.071*
C9	0.8830 (7)	0.3623 (4)	0.1907 (3)	0.0569 (8)
H9A	1.0565	0.3590	0.2325	0.085*
H9B	0.9069	0.4011	0.1006	0.085*
H9C	0.8435	0.2681	0.2168	0.085*
C10	0.1310 (10)	0.8109 (4)	0.0632 (4)	0.0815 (12)
H10A	0.2775	0.8560	0.0104	0.122*
H10B	0.0287	0.8712	0.1032	0.122*
H10C	−0.0013	0.7944	0.0121	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0551 (6)	0.1112 (9)	0.0893 (8)	−0.0082 (5)	0.0147 (5)	0.0236 (6)
O1	0.0134 (9)	0.0749 (15)	0.0926 (17)	−0.0115 (9)	−0.0051 (10)	−0.0006 (13)
N1	0.0138 (9)	0.0512 (13)	0.0519 (13)	−0.0051 (9)	−0.0010 (9)	−0.0132 (11)
C1	0.0211 (12)	0.0446 (15)	0.0476 (15)	−0.0062 (10)	−0.0031 (10)	−0.0166 (12)
C2	0.0263 (13)	0.0534 (17)	0.0504 (15)	−0.0104 (11)	0.0017 (11)	−0.0213 (13)
C3	0.0456 (17)	0.0573 (18)	0.0484 (16)	−0.0122 (14)	−0.0006 (13)	−0.0141 (14)
C4	0.0493 (18)	0.0474 (17)	0.0599 (18)	−0.0044 (13)	−0.0087 (14)	−0.0160 (14)
C5	0.0394 (16)	0.0548 (18)	0.0628 (19)	0.0047 (13)	−0.0037 (13)	−0.0242 (15)
C6	0.0278 (13)	0.0567 (17)	0.0503 (16)	−0.0021 (12)	0.0016 (11)	−0.0195 (13)
C7	0.0174 (12)	0.0522 (16)	0.0586 (17)	−0.0060 (11)	−0.0004 (11)	−0.0147 (13)
C8	0.0233 (13)	0.0593 (19)	0.073 (2)	−0.0076 (12)	−0.0009 (13)	−0.0021 (16)
C9	0.0369 (16)	0.072 (2)	0.0603 (18)	−0.0050 (14)	0.0090 (14)	−0.0270 (16)
C10	0.087 (3)	0.059 (2)	0.075 (2)	0.006 (2)	−0.009 (2)	−0.0087 (19)

Geometric parameters (Å, º) top

Cl1—C8	1.728 (3)	C5—C6	1.371 (4)
O1—C7	1.223 (3)	C5—H5	0.9300
N1—C7	1.333 (4)	C6—H6	0.9300
N1—C1	1.425 (3)	C7—C8	1.516 (4)
N1—H1N	0.83 (4)	C8—H8A	0.9700
C1—C2	1.389 (4)	C8—H8B	0.9700
C1—C6	1.392 (4)	C9—H9A	0.9600
C2—C3	1.390 (4)	C9—H9B	0.9600
C2—C9	1.506 (4)	C9—H9C	0.9600
C3—C4	1.390 (5)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.378 (5)	C10—H10C	0.9600
C4—C10	1.511 (5)

C7—N1—C1	124.3 (2)	O1—C7—N1	123.9 (3)
C7—N1—H1N	119 (2)	O1—C7—C8	121.4 (3)
C1—N1—H1N	117 (2)	N1—C7—C8	114.6 (2)
C2—C1—C6	120.4 (3)	C7—C8—Cl1	112.3 (2)
C2—C1—N1	120.0 (2)	C7—C8—H8A	109.1
C6—C1—N1	119.6 (2)	Cl1—C8—H8A	109.1
C1—C2—C3	117.6 (3)	C7—C8—H8B	109.1
C1—C2—C9	121.6 (3)	Cl1—C8—H8B	109.1
C3—C2—C9	120.9 (3)	H8A—C8—H8B	107.9
C4—C3—C2	122.8 (3)	C2—C9—H9A	109.5
C4—C3—H3	118.6	C2—C9—H9B	109.5
C2—C3—H3	118.6	H9A—C9—H9B	109.5
C5—C4—C3	117.8 (3)	C2—C9—H9C	109.5
C5—C4—C10	120.9 (3)	H9A—C9—H9C	109.5
C3—C4—C10	121.2 (3)	H9B—C9—H9C	109.5
C6—C5—C4	121.2 (3)	C4—C10—H10A	109.5
C6—C5—H5	119.4	C4—C10—H10B	109.5
C4—C5—H5	119.4	H10A—C10—H10B	109.5
C5—C6—C1	120.3 (3)	C4—C10—H10C	109.5
C5—C6—H6	119.9	H10A—C10—H10C	109.5
C1—C6—H6	119.9	H10B—C10—H10C	109.5

C7—N1—C1—C2	−130.4 (3)	C3—C4—C5—C6	0.7 (5)
C7—N1—C1—C6	50.8 (4)	C10—C4—C5—C6	−179.0 (3)
C6—C1—C2—C3	0.7 (4)	C4—C5—C6—C1	−0.8 (5)
N1—C1—C2—C3	−178.1 (2)	C2—C1—C6—C5	0.1 (4)
C6—C1—C2—C9	−179.1 (3)	N1—C1—C6—C5	178.9 (3)
N1—C1—C2—C9	2.1 (4)	C1—N1—C7—O1	2.5 (5)
C1—C2—C3—C4	−0.9 (4)	C1—N1—C7—C8	−178.9 (3)
C9—C2—C3—C4	178.9 (3)	O1—C7—C8—Cl1	−25.2 (4)
C2—C3—C4—C5	0.2 (5)	N1—C7—C8—Cl1	156.2 (3)
C2—C3—C4—C10	179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (4)	2.04 (4)	2.853 (3)	165 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂ClNO
M_r	197.66
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	4.7235 (7), 10.407 (2), 11.451 (2)
α, β, γ (°)	67.07 (2), 86.84 (1), 78.95 (2)
V (Å³)	508.69 (15)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.00
Crystal size (mm)	0.60 × 0.06 × 0.04

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan North et al. (1968)
T_min, T_max	0.803, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	2059, 1817, 1394
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.190, 1.09
No. of reflections	1817
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)	0.45, −0.47

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), 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
N1—H1N···O1ⁱ	0.83 (4)	2.04 (4)	2.853 (3)	165 (3)

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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