Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031728/im2020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031728/im2020Isup2.hkl |
CCDC reference: 657659
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.
The H atoms were located from the difference Fourier map and their positions refined with Uiso(H) = 1.2 Ueq (parent atom).
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).
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).
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.
C10H10Cl3NO | F(000) = 544 |
Mr = 266.54 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 2291 reflections |
a = 4.7310 (6) Å | θ = 2.6–24.4° |
b = 24.042 (2) Å | µ = 0.73 mm−1 |
c = 10.799 (1) Å | T = 297 K |
β = 98.01 (1)° | Needle, colourless |
V = 1216.3 (2) Å3 | 0.50 × 0.12 × 0.06 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2460 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1574 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.4°, θmin = 4.2° |
Rotation method data acquisition using ω and φ scans | h = −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 = 0.958 | l = −13→13 |
8334 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H 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 reflections | Δρmax = 0.36 e Å−3 |
145 parameters | Δρmin = −0.34 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0137 (15) |
C10H10Cl3NO | V = 1216.3 (2) Å3 |
Mr = 266.54 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.7310 (6) Å | µ = 0.73 mm−1 |
b = 24.042 (2) Å | T = 297 K |
c = 10.799 (1) Å | 0.50 × 0.12 × 0.06 mm |
β = 98.01 (1)° |
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 = 0.958 | Rint = 0.039 |
8334 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.36 e Å−3 |
2460 reflections | Δρmin = −0.34 e Å−3 |
145 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8638 (6) | 0.09310 (12) | 0.2959 (3) | 0.0344 (7) | |
C2 | 0.7415 (7) | 0.06534 (13) | 0.1894 (3) | 0.0387 (8) | |
C3 | 0.8267 (7) | 0.01277 (13) | 0.1585 (3) | 0.0467 (9) | |
H3 | 0.7398 | −0.0051 | 0.0868 | 0.056* | |
C4 | 1.0425 (8) | −0.01217 (13) | 0.2364 (4) | 0.0504 (9) | |
C5 | 1.1702 (8) | 0.01276 (14) | 0.3435 (3) | 0.0516 (9) | |
H5 | 1.3160 | −0.0050 | 0.3954 | 0.062* | |
C6 | 1.0776 (7) | 0.06514 (14) | 0.3730 (3) | 0.0427 (8) | |
C7 | 0.9518 (7) | 0.19206 (13) | 0.3283 (3) | 0.0380 (8) | |
C8 | 0.8228 (7) | 0.24621 (14) | 0.3627 (4) | 0.0503 (9) | |
H8 | 0.624 (8) | 0.2474 (14) | 0.326 (3) | 0.060* | |
C9 | 0.9660 (9) | 0.29551 (15) | 0.3124 (5) | 0.0736 (13) | |
H9A | 0.9525 | 0.2925 | 0.2231 | 0.088* | |
H9B | 1.1633 | 0.2964 | 0.3484 | 0.088* | |
H9C | 0.8736 | 0.3291 | 0.3335 | 0.088* | |
C10 | 0.8362 (14) | 0.2489 (2) | 0.5023 (5) | 0.114 (2) | |
H10A | 1.0320 | 0.2500 | 0.5403 | 0.137* | |
H10B | 0.7454 | 0.2166 | 0.5311 | 0.137* | |
H10C | 0.7396 | 0.2817 | 0.5247 | 0.137* | |
N1 | 0.7771 (5) | 0.14716 (11) | 0.3235 (3) | 0.0378 (7) | |
H1 | 0.612 (7) | 0.1525 (14) | 0.323 (3) | 0.045* | |
O1 | 1.1986 (5) | 0.18779 (9) | 0.3089 (3) | 0.0553 (7) | |
Cl1 | 0.4698 (2) | 0.09734 (4) | 0.09091 (9) | 0.0612 (3) | |
Cl2 | 1.1579 (3) | −0.07790 (4) | 0.19711 (12) | 0.0811 (4) | |
Cl3 | 1.2321 (2) | 0.09475 (4) | 0.51250 (9) | 0.0664 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0292 (16) | 0.0317 (16) | 0.0439 (17) | −0.0019 (14) | 0.0108 (14) | −0.0012 (15) |
C2 | 0.0346 (17) | 0.0366 (18) | 0.0439 (18) | −0.0016 (14) | 0.0025 (15) | 0.0015 (15) |
C3 | 0.051 (2) | 0.0364 (18) | 0.053 (2) | −0.0018 (17) | 0.0069 (17) | −0.0129 (16) |
C4 | 0.055 (2) | 0.0306 (17) | 0.067 (2) | 0.0045 (17) | 0.0132 (19) | −0.0036 (17) |
C5 | 0.054 (2) | 0.0374 (19) | 0.060 (2) | 0.0092 (17) | −0.0016 (18) | 0.0010 (17) |
C6 | 0.0432 (19) | 0.0400 (19) | 0.0445 (19) | −0.0037 (16) | 0.0045 (16) | −0.0009 (15) |
C7 | 0.0301 (17) | 0.0353 (17) | 0.0480 (19) | −0.0023 (15) | 0.0033 (15) | −0.0055 (15) |
C8 | 0.0336 (18) | 0.0375 (19) | 0.081 (3) | −0.0016 (16) | 0.0139 (19) | −0.0164 (18) |
C9 | 0.078 (3) | 0.037 (2) | 0.109 (4) | 0.002 (2) | 0.022 (3) | −0.002 (2) |
C10 | 0.198 (6) | 0.067 (3) | 0.092 (4) | −0.006 (4) | 0.069 (4) | −0.029 (3) |
N1 | 0.0254 (13) | 0.0336 (14) | 0.0556 (17) | −0.0005 (12) | 0.0095 (13) | −0.0090 (12) |
O1 | 0.0287 (13) | 0.0439 (14) | 0.096 (2) | −0.0027 (11) | 0.0178 (12) | −0.0062 (13) |
Cl1 | 0.0599 (6) | 0.0559 (6) | 0.0614 (6) | 0.0128 (5) | −0.0142 (5) | −0.0093 (5) |
Cl2 | 0.0946 (9) | 0.0417 (5) | 0.1062 (9) | 0.0224 (5) | 0.0108 (7) | −0.0166 (6) |
Cl3 | 0.0807 (8) | 0.0583 (6) | 0.0527 (6) | 0.0012 (5) | −0.0165 (5) | −0.0049 (5) |
C1—C2 | 1.385 (4) | C7—N1 | 1.356 (4) |
C1—C6 | 1.391 (4) | C7—C8 | 1.506 (4) |
C1—N1 | 1.407 (4) | C8—C10 | 1.501 (6) |
C2—C3 | 1.382 (4) | C8—C9 | 1.504 (5) |
C2—Cl1 | 1.731 (3) | C8—H8 | 0.97 (4) |
C3—C4 | 1.368 (5) | C9—H9A | 0.9600 |
C3—H3 | 0.9300 | C9—H9B | 0.9600 |
C4—C5 | 1.367 (5) | C9—H9C | 0.9600 |
C4—Cl2 | 1.743 (3) | C10—H10A | 0.9600 |
C5—C6 | 1.385 (5) | C10—H10B | 0.9600 |
C5—H5 | 0.9300 | C10—H10C | 0.9600 |
C6—Cl3 | 1.733 (3) | N1—H1 | 0.79 (3) |
C7—O1 | 1.219 (3) | ||
C2—C1—C6 | 116.7 (3) | C10—C8—C9 | 111.8 (4) |
C2—C1—N1 | 121.4 (3) | C10—C8—C7 | 108.8 (4) |
C6—C1—N1 | 121.9 (3) | C9—C8—C7 | 111.9 (3) |
C3—C2—C1 | 122.6 (3) | C10—C8—H8 | 108 (2) |
C3—C2—Cl1 | 118.4 (3) | C9—C8—H8 | 107 (2) |
C1—C2—Cl1 | 119.0 (2) | C7—C8—H8 | 109 (2) |
C4—C3—C2 | 118.1 (3) | C8—C9—H9A | 109.5 |
C4—C3—H3 | 121.0 | C8—C9—H9B | 109.5 |
C2—C3—H3 | 121.0 | H9A—C9—H9B | 109.5 |
C5—C4—C3 | 122.2 (3) | C8—C9—H9C | 109.5 |
C5—C4—Cl2 | 119.1 (3) | H9A—C9—H9C | 109.5 |
C3—C4—Cl2 | 118.7 (3) | H9B—C9—H9C | 109.5 |
C4—C5—C6 | 118.5 (3) | C8—C10—H10A | 109.5 |
C4—C5—H5 | 120.8 | C8—C10—H10B | 109.5 |
C6—C5—H5 | 120.8 | H10A—C10—H10B | 109.5 |
C5—C6—C1 | 121.9 (3) | C8—C10—H10C | 109.5 |
C5—C6—Cl3 | 117.7 (3) | H10A—C10—H10C | 109.5 |
C1—C6—Cl3 | 120.4 (3) | H10B—C10—H10C | 109.5 |
O1—C7—N1 | 121.3 (3) | C7—N1—C1 | 123.3 (3) |
O1—C7—C8 | 123.1 (3) | C7—N1—H1 | 118 (3) |
N1—C7—C8 | 115.6 (3) | C1—N1—H1 | 118 (3) |
C6—C1—C2—C3 | −0.8 (5) | C2—C1—C6—C5 | 1.8 (5) |
N1—C1—C2—C3 | 178.5 (3) | N1—C1—C6—C5 | −177.6 (3) |
C6—C1—C2—Cl1 | 178.8 (2) | C2—C1—C6—Cl3 | −176.8 (2) |
N1—C1—C2—Cl1 | −1.8 (4) | N1—C1—C6—Cl3 | 3.9 (4) |
C1—C2—C3—C4 | −0.6 (5) | O1—C7—C8—C10 | −96.7 (4) |
Cl1—C2—C3—C4 | 179.7 (3) | N1—C7—C8—C10 | 81.4 (4) |
C2—C3—C4—C5 | 1.3 (5) | O1—C7—C8—C9 | 27.4 (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—C6 | 179.6 (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—Cl3 | 177.4 (3) | C6—C1—N1—C7 | 63.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.79 (3) | 2.12 (3) | 2.889 (3) | 165 (3) |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C10H10Cl3NO |
Mr | 266.54 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 4.7310 (6), 24.042 (2), 10.799 (1) |
β (°) | 98.01 (1) |
V (Å3) | 1216.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.73 |
Crystal size (mm) | 0.50 × 0.12 × 0.06 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
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)] |
Tmin, Tmax | 0.713, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8334, 2460, 1574 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.126, 1.08 |
No. of reflections | 2460 |
No. of parameters | 145 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.34 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.79 (3) | 2.12 (3) | 2.889 (3) | 165 (3) |
Symmetry code: (i) x−1, y, z. |
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).