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Acta Cryst. (2007). E63, o3366    [ doi:10.1107/S1600536807031728 ]

2,2-Dimethyl-N-(2,4,6-trichlorophenyl)acetamide

B. T. Gowda, I. Svoboda and H. Fuess

Abstract top

The structure of the title compound, C10H10Cl3NO, is similar to that of N-(2,4,6-trichlorophenyl)-chloro/methyl-acetamides and other acetanilides, with somewhat different geometric parameters. Comparison of the geometric parameters of the title compound with those of the ring and side-chain-substituted acetanilides reveals that substitution either in the benzene ring or in the side chain of the amides changes some of the space groups but also some of the bond lengths, and bond and torsion angles. The molecules in the title compound are packed into chains through N-H...O hydrogen bonding.

Comment top

As part of a study on the effect of side chain and ring substitutions on the solid state structures of a chemically and biologically significant class of compounds (Gowda et al., 2000; 2004b; 2006; 2007a, b), in the present work, the crystal structure of N-(2,4,6-trichlorophenyl)-2,2-dimethylacetamide (246TCPDMA) has been determined. The structure of 246TCPDMA (Fig. 1) is similar to those of N-(2,4,6-trichlorophenyl)-chloro/methyl-acetamides and other acetanilides, with somewhat different geometric parameters (Gowda et al., 2000; 2004b; 2006; 2007a, b; Mahalakshmi et al., 2002; Nyburg et al., 1987). The comparison of the geometric parameters of the title compound with those of the ring and side chain substituted acetanilides revealed that substitution either in the benzene ring or in the side chain of the amides not only changes the space groups but also some of the bond lengths as well as bond and torsional angles (Gowda et al., 2000; 2004a; 2006; 2007a, b). But to draw general conclusions further substantive data are to be collected with varying substitution patterns. The molecules in the title compound are packed into chains through N—H···O hydrogen bonding (Table 1 & Fig.2).

Related literature top

For related literature, see: Gowda et al. (2000, 2006); Gowda, Svoboda & Fuess (2004); Gowda, Usha & Jyothi (2004); Gowda, Foro et al. (2007); Gowda, Kozisek et al. (2007); Mahalakshmi et al. (2002); Nyburg et al. (1987).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2004b). 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., 2004b). Single crystals of the title compound were obtained from a slow evaporation of an ethanolic solution (2 g in about 30 ml e thanol) and used for X-ray diffraction studies at room temperature.

Refinement top

The H atoms were located from the difference Fourier map and their positions refined with Uiso(H) = 1.2 Ueq (parent atom).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Hydrogen bonding in the title compound. Hydrogen bonds are shown as dashed lines.
2,2-Dimethyl-N-(2,4,6-trichlorophenyl)acetamide top
Crystal data top
C10H10Cl3NOF(000) = 544
Mr = 266.54Dx = 1.456 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 2291 reflections
a = 4.7310 (6) Åθ = 2.6–24.4°
b = 24.042 (2) ŵ = 0.73 mm−1
c = 10.799 (1) ÅT = 297 K
β = 98.01 (1)°Needle, colourless
V = 1216.3 (2) Å30.50 × 0.12 × 0.06 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2460 independent reflections
Radiation source: Enhance (Mo) X-ray Source1574 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 8.4012 pixels mm-1θmax = 26.4°, θmin = 4.2°
Rotation method data acquisition using ω and φ scansh = −5→5
Absorption correction: multi-scan
[CrysAlis RED (Oxford Diffraction, 2006); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]		k = −29→27
Tmin = 0.713, Tmax = 0.958l = −13→13
8334 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0366P)2 + 1.2703P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
2460 reflectionsΔρmax = 0.36 e Å−3
145 parametersΔρmin = −0.34 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0137 (15)
Crystal data top
C10H10Cl3NOV = 1216.3 (2) Å3
Mr = 266.54Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.7310 (6) ŵ = 0.73 mm−1
b = 24.042 (2) ÅT = 297 K
c = 10.799 (1) Å0.50 × 0.12 × 0.06 mm
β = 98.01 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2460 independent reflections
Absorption correction: multi-scan
[CrysAlis RED (Oxford Diffraction, 2006); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]		1574 reflections with I > 2σ(I)
Tmin = 0.713, Tmax = 0.958Rint = 0.039
8334 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.060H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126Δρmax = 0.36 e Å−3
S = 1.08Δρmin = −0.34 e Å−3
2460 reflectionsAbsolute structure: ?
145 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.8638 (6)0.09310 (12)0.2959 (3)0.0344 (7)
C20.7415 (7)0.06534 (13)0.1894 (3)0.0387 (8)
C30.8267 (7)0.01277 (13)0.1585 (3)0.0467 (9)
H30.7398−0.00510.08680.056*
C41.0425 (8)−0.01217 (13)0.2364 (4)0.0504 (9)
C51.1702 (8)0.01276 (14)0.3435 (3)0.0516 (9)
H51.3160−0.00500.39540.062*
C61.0776 (7)0.06514 (14)0.3730 (3)0.0427 (8)
C70.9518 (7)0.19206 (13)0.3283 (3)0.0380 (8)
C80.8228 (7)0.24621 (14)0.3627 (4)0.0503 (9)
H80.624 (8)0.2474 (14)0.326 (3)0.060*
C90.9660 (9)0.29551 (15)0.3124 (5)0.0736 (13)
H9A0.95250.29250.22310.088*
H9B1.16330.29640.34840.088*
H9C0.87360.32910.33350.088*
C100.8362 (14)0.2489 (2)0.5023 (5)0.114 (2)
H10A1.03200.25000.54030.137*
H10B0.74540.21660.53110.137*
H10C0.73960.28170.52470.137*
N10.7771 (5)0.14716 (11)0.3235 (3)0.0378 (7)
H10.612 (7)0.1525 (14)0.323 (3)0.045*
O11.1986 (5)0.18779 (9)0.3089 (3)0.0553 (7)
Cl10.4698 (2)0.09734 (4)0.09091 (9)0.0612 (3)
Cl21.1579 (3)−0.07790 (4)0.19711 (12)0.0811 (4)
Cl31.2321 (2)0.09475 (4)0.51250 (9)0.0664 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0292 (16)0.0317 (16)0.0439 (17)−0.0019 (14)0.0108 (14)−0.0012 (15)
C20.0346 (17)0.0366 (18)0.0439 (18)−0.0016 (14)0.0025 (15)0.0015 (15)
C30.051 (2)0.0364 (18)0.053 (2)−0.0018 (17)0.0069 (17)−0.0129 (16)
C40.055 (2)0.0306 (17)0.067 (2)0.0045 (17)0.0132 (19)−0.0036 (17)
C50.054 (2)0.0374 (19)0.060 (2)0.0092 (17)−0.0016 (18)0.0010 (17)
C60.0432 (19)0.0400 (19)0.0445 (19)−0.0037 (16)0.0045 (16)−0.0009 (15)
C70.0301 (17)0.0353 (17)0.0480 (19)−0.0023 (15)0.0033 (15)−0.0055 (15)
C80.0336 (18)0.0375 (19)0.081 (3)−0.0016 (16)0.0139 (19)−0.0164 (18)
C90.078 (3)0.037 (2)0.109 (4)0.002 (2)0.022 (3)−0.002 (2)
C100.198 (6)0.067 (3)0.092 (4)−0.006 (4)0.069 (4)−0.029 (3)
N10.0254 (13)0.0336 (14)0.0556 (17)−0.0005 (12)0.0095 (13)−0.0090 (12)
O10.0287 (13)0.0439 (14)0.096 (2)−0.0027 (11)0.0178 (12)−0.0062 (13)
Cl10.0599 (6)0.0559 (6)0.0614 (6)0.0128 (5)−0.0142 (5)−0.0093 (5)
Cl20.0946 (9)0.0417 (5)0.1062 (9)0.0224 (5)0.0108 (7)−0.0166 (6)
Cl30.0807 (8)0.0583 (6)0.0527 (6)0.0012 (5)−0.0165 (5)−0.0049 (5)
Geometric parameters (Å, °) top
C1—C21.385 (4)C7—N11.356 (4)
C1—C61.391 (4)C7—C81.506 (4)
C1—N11.407 (4)C8—C101.501 (6)
C2—C31.382 (4)C8—C91.504 (5)
C2—Cl11.731 (3)C8—H80.97 (4)
C3—C41.368 (5)C9—H9A0.9600
C3—H30.9300C9—H9B0.9600
C4—C51.367 (5)C9—H9C0.9600
C4—Cl21.743 (3)C10—H10A0.9600
C5—C61.385 (5)C10—H10B0.9600
C5—H50.9300C10—H10C0.9600
C6—Cl31.733 (3)N1—H10.79 (3)
C7—O11.219 (3)
C2—C1—C6116.7 (3)C10—C8—C9111.8 (4)
C2—C1—N1121.4 (3)C10—C8—C7108.8 (4)
C6—C1—N1121.9 (3)C9—C8—C7111.9 (3)
C3—C2—C1122.6 (3)C10—C8—H8108 (2)
C3—C2—Cl1118.4 (3)C9—C8—H8107 (2)
C1—C2—Cl1119.0 (2)C7—C8—H8109 (2)
C4—C3—C2118.1 (3)C8—C9—H9A109.5
C4—C3—H3121.0C8—C9—H9B109.5
C2—C3—H3121.0H9A—C9—H9B109.5
C5—C4—C3122.2 (3)C8—C9—H9C109.5
C5—C4—Cl2119.1 (3)H9A—C9—H9C109.5
C3—C4—Cl2118.7 (3)H9B—C9—H9C109.5
C4—C5—C6118.5 (3)C8—C10—H10A109.5
C4—C5—H5120.8C8—C10—H10B109.5
C6—C5—H5120.8H10A—C10—H10B109.5
C5—C6—C1121.9 (3)C8—C10—H10C109.5
C5—C6—Cl3117.7 (3)H10A—C10—H10C109.5
C1—C6—Cl3120.4 (3)H10B—C10—H10C109.5
O1—C7—N1121.3 (3)C7—N1—C1123.3 (3)
O1—C7—C8123.1 (3)C7—N1—H1118 (3)
N1—C7—C8115.6 (3)C1—N1—H1118 (3)
C6—C1—C2—C3−0.8 (5)C2—C1—C6—C51.8 (5)
N1—C1—C2—C3178.5 (3)N1—C1—C6—C5−177.6 (3)
C6—C1—C2—Cl1178.8 (2)C2—C1—C6—Cl3−176.8 (2)
N1—C1—C2—Cl1−1.8 (4)N1—C1—C6—Cl33.9 (4)
C1—C2—C3—C4−0.6 (5)O1—C7—C8—C10−96.7 (4)
Cl1—C2—C3—C4179.7 (3)N1—C7—C8—C1081.4 (4)
C2—C3—C4—C51.3 (5)O1—C7—C8—C927.4 (5)
C2—C3—C4—Cl2−178.7 (3)N1—C7—C8—C9−154.5 (3)
C3—C4—C5—C6−0.4 (6)O1—C7—N1—C1−0.3 (5)
Cl2—C4—C5—C6179.6 (3)C8—C7—N1—C1−178.4 (3)
C4—C5—C6—C1−1.2 (5)C2—C1—N1—C7−115.8 (3)
C4—C5—C6—Cl3177.4 (3)C6—C1—N1—C763.5 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.79 (3)2.12 (3)2.889 (3)165 (3)
Symmetry codes: (i) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.79 (3)2.12 (3)2.889 (3)165 (3)
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

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

references
References top

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