Acta Cryst. (2008). E64, o420 [ doi:10.1107/S1600536808000366 ]
The structure of the title compound, C8H6Cl3NO, is closely related to that of N-(3,5-dichlorophenyl)acetamide and other amides. The molecular skeleton is essentially planar. The molecules in the crystal structure are stabilized by N-H
O and N-HCl intermolecular hydrogen bonds running along the a axis
The title compound was prepared according to the literature method (Shilpa & 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 & Gowda, 2007). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.
The CH atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.97 Å. The NH atom was located in difference map with N—H = 0.86 Å. Uiso(H) values were set equal to 1.2 Ueq of the parent atom.
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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./om2202fig1thm.gif)
| Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./om2202fig2thm.gif)
| Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines. |
| C8H6Cl3NO | F000 = 480 |
| Mr = 238.49 | Dx = 1.637 Mg m−3 |
| Monoclinic, P21/n | Cu Kα radiation λ = 1.54180 Å |
| Hall symbol: -P 2yn | Cell parameters from 25 reflections |
| a = 4.567 (1) Å | θ = 6.2–23.2º |
| b = 24.350 (4) Å | µ = 8.23 mm−1 |
| c = 8.903 (2) Å | T = 299 (2) K |
| β = 102.20 (2)º | Long plate, colourless |
| V = 967.7 (3) Å3 | 0.60 × 0.35 × 0.13 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.074 |
| Radiation source: fine-focus sealed tube | θmax = 66.9º |
| Monochromator: graphite | θmin = 3.6º |
| T = 299(2) K | h = 0→5 |
| ω/2θ scans | k = −29→23 |
| Absorption correction: ψ scan (North et al., 1968) | l = −10→10 |
| Tmin = 0.063, Tmax = 0.354 | 3 standard reflections |
| 3732 measured reflections | every 120 min |
| 1730 independent reflections | intensity decay: 1.0% |
| 1606 reflections with I > 2σ(I) |
| 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)] = 0.098 | H-atom parameters constrained |
| wR(F2) = 0.288 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.39 | (Δ/σ)max = 0.005 |
| 1730 reflections | Δρmax = 0.57 e Å−3 |
| 118 parameters | Δρmin = −1.12 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C8H6Cl3NO | V = 967.7 (3) Å3 |
| Mr = 238.49 | Z = 4 |
| Monoclinic, P21/n | Cu Kα |
| a = 4.567 (1) Å | µ = 8.23 mm−1 |
| b = 24.350 (4) Å | T = 299 (2) K |
| c = 8.903 (2) Å | 0.60 × 0.35 × 0.13 mm |
| β = 102.20 (2)º |
| Enraf–Nonius CAD-4 diffractometer | 1606 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.074 |
| Tmin = 0.063, Tmax = 0.354 | 3 standard reflections |
| 3732 measured reflections | every 120 min |
| 1730 independent reflections | intensity decay: 1.0% |
| R[F2 > 2σ(F2)] = 0.098 | 118 parameters |
| wR(F2) = 0.288 | H-atom parameters constrained |
| S = 1.39 | Δρmax = 0.57 e Å−3 |
| 1730 reflections | Δρmin = −1.12 e Å−3 |
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 | 0.7994 (8) | 0.15227 (14) | 0.4676 (4) | 0.0509 (8) | |
| C2 | 0.9691 (7) | 0.12475 (16) | 0.5925 (4) | 0.0528 (9) | |
| H2 | 0.9617 | 0.1353 | 0.6921 | 0.063* | |
| C3 | 1.1486 (9) | 0.08169 (15) | 0.5677 (5) | 0.0585 (10) | |
| C4 | 1.1657 (10) | 0.06515 (16) | 0.4216 (5) | 0.0639 (10) | |
| H4 | 1.2884 | 0.0362 | 0.4059 | 0.077* | |
| C5 | 0.9960 (10) | 0.09289 (17) | 0.3011 (5) | 0.0615 (10) | |
| C6 | 0.8060 (8) | 0.13604 (15) | 0.3183 (4) | 0.0553 (9) | |
| H6 | 0.6881 | 0.1533 | 0.2336 | 0.066* | |
| C7 | 0.4446 (7) | 0.23062 (14) | 0.4049 (4) | 0.0466 (8) | |
| C8 | 0.3181 (8) | 0.27475 (16) | 0.4947 (4) | 0.0539 (9) | |
| H8A | 0.4787 | 0.2992 | 0.5425 | 0.065* | |
| H8B | 0.2388 | 0.2575 | 0.5758 | 0.065* | |
| N1 | 0.6266 (7) | 0.19666 (13) | 0.5008 (3) | 0.0513 (8) | |
| H1N | 0.6394 | 0.2030 | 0.5970 | 0.062* | |
| O1 | 0.3874 (5) | 0.22828 (12) | 0.2651 (3) | 0.0560 (8) | |
| Cl1 | 1.3597 (3) | 0.04771 (4) | 0.72484 (15) | 0.0797 (6) | |
| Cl2 | 1.0161 (4) | 0.07364 (6) | 0.11529 (14) | 0.0948 (6) | |
| Cl3 | 0.0336 (2) | 0.31342 (4) | 0.37802 (10) | 0.0626 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0514 (16) | 0.0467 (17) | 0.0520 (18) | −0.0028 (13) | 0.0048 (14) | 0.0006 (14) |
| C2 | 0.0540 (19) | 0.0512 (18) | 0.0503 (18) | −0.0072 (14) | 0.0042 (14) | −0.0012 (14) |
| C3 | 0.057 (2) | 0.0451 (17) | 0.068 (2) | −0.0029 (14) | −0.0001 (17) | 0.0021 (16) |
| C4 | 0.073 (2) | 0.0481 (17) | 0.071 (2) | 0.0086 (17) | 0.0157 (19) | −0.0015 (18) |
| C5 | 0.073 (2) | 0.055 (2) | 0.059 (2) | −0.0001 (16) | 0.0189 (17) | −0.0056 (16) |
| C6 | 0.064 (2) | 0.0501 (19) | 0.051 (2) | −0.0011 (15) | 0.0115 (16) | −0.0001 (15) |
| C7 | 0.0435 (15) | 0.0520 (17) | 0.0421 (16) | −0.0029 (13) | 0.0038 (12) | 0.0003 (13) |
| C8 | 0.0540 (18) | 0.062 (2) | 0.0406 (17) | 0.0106 (15) | −0.0004 (13) | −0.0021 (14) |
| N1 | 0.0544 (15) | 0.0573 (16) | 0.0382 (14) | 0.0062 (12) | 0.0010 (12) | −0.0012 (12) |
| O1 | 0.0566 (14) | 0.0654 (16) | 0.0413 (13) | 0.0070 (11) | −0.0002 (10) | −0.0017 (11) |
| Cl1 | 0.0871 (9) | 0.0616 (8) | 0.0782 (9) | 0.0179 (5) | −0.0100 (7) | 0.0057 (5) |
| Cl2 | 0.1422 (14) | 0.0816 (10) | 0.0661 (9) | 0.0296 (7) | 0.0342 (8) | −0.0070 (6) |
| Cl3 | 0.0580 (7) | 0.0717 (8) | 0.0538 (8) | 0.0174 (4) | 0.0023 (5) | 0.0058 (4) |
| C1—C2 | 1.387 (5) | C5—Cl2 | 1.740 (4) |
| C1—C6 | 1.393 (5) | C6—H6 | 0.9300 |
| C1—N1 | 1.406 (5) | C7—O1 | 1.218 (4) |
| C2—C3 | 1.377 (5) | C7—N1 | 1.343 (5) |
| C2—H2 | 0.9300 | C7—C8 | 1.524 (5) |
| C3—C4 | 1.380 (6) | C8—Cl3 | 1.756 (3) |
| C3—Cl1 | 1.732 (4) | C8—H8A | 0.9700 |
| C4—C5 | 1.363 (6) | C8—H8B | 0.9700 |
| C4—H4 | 0.9300 | N1—H1N | 0.8600 |
| C5—C6 | 1.392 (5) | ||
| C2—C1—C6 | 120.5 (3) | C5—C6—C1 | 117.3 (3) |
| C2—C1—N1 | 116.5 (3) | C5—C6—H6 | 121.3 |
| C6—C1—N1 | 123.0 (3) | C1—C6—H6 | 121.3 |
| C3—C2—C1 | 119.3 (3) | O1—C7—N1 | 126.2 (3) |
| C3—C2—H2 | 120.3 | O1—C7—C8 | 123.1 (3) |
| C1—C2—H2 | 120.3 | N1—C7—C8 | 110.7 (3) |
| C2—C3—C4 | 121.9 (3) | C7—C8—Cl3 | 112.5 (2) |
| C2—C3—Cl1 | 118.9 (3) | C7—C8—H8A | 109.1 |
| C4—C3—Cl1 | 119.3 (3) | Cl3—C8—H8A | 109.1 |
| C5—C4—C3 | 117.5 (4) | C7—C8—H8B | 109.1 |
| C5—C4—H4 | 121.3 | Cl3—C8—H8B | 109.1 |
| C3—C4—H4 | 121.3 | H8A—C8—H8B | 107.8 |
| C4—C5—C6 | 123.5 (3) | C7—N1—C1 | 129.7 (3) |
| C4—C5—Cl2 | 118.6 (3) | C7—N1—H1N | 115.1 |
| C6—C5—Cl2 | 117.9 (3) | C1—N1—H1N | 115.1 |
| C6—C1—C2—C3 | 1.1 (5) | Cl2—C5—C6—C1 | −177.9 (3) |
| N1—C1—C2—C3 | −178.5 (3) | C2—C1—C6—C5 | −2.2 (5) |
| C1—C2—C3—C4 | 0.3 (6) | N1—C1—C6—C5 | 177.4 (3) |
| C1—C2—C3—Cl1 | 179.9 (3) | O1—C7—C8—Cl3 | 10.7 (5) |
| C2—C3—C4—C5 | −0.4 (6) | N1—C7—C8—Cl3 | −170.4 (3) |
| Cl1—C3—C4—C5 | 179.9 (3) | O1—C7—N1—C1 | 2.0 (6) |
| C3—C4—C5—C6 | −0.9 (6) | C8—C7—N1—C1 | −176.8 (3) |
| C3—C4—C5—Cl2 | 179.2 (3) | C2—C1—N1—C7 | 179.5 (3) |
| C4—C5—C6—C1 | 2.1 (6) | C6—C1—N1—C7 | 0.0 (6) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.37 | 3.019 (4) | 133 |
| N1—H1N···Cl3i | 0.86 | 2.68 | 3.482 (3) | 156 |
| Symmetry codes: (i) x+1/2, −y+1/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.37 | 3.019 (4) | 133 |
| N1—H1N···Cl3i | 0.86 | 2.68 | 3.482 (3) | 156 |
| Symmetry codes: (i) x+1/2, −y+1/2, z+1/2. |
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
Enraf–Nonius (1996). CAD-4-PC. Version 1.2. Enraf–Nonius, Delft, The Netherlands.
Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2341–o2342.
Gowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o4488–?.
Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
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Shilpa & Gowda, B. T. (2007). Z. Naturforsch. Teil A, 62, 84–90.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
Stoe & Cie (1987). REDU4. Version 6.2c. Stoe & Cie GmbH, Darmstadt, Germany.
In the present work, the structure of 2-chloro-N-(3,5-dichlorophenyl)- acetamide (35DCPCA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda et al., 2007a, b; Gowda et al., 2007). The structure of 35DCPCA (Fig. 1) is closely related to 2-chloro-N-(2-chlorophenyl)acetamide (2CPCA), 2-chloro-N-(4-chlorophenyl)acetamide (4CPCA)(Gowda et al., 2007b), N-(3,5-dichlorophenyl)-acetamide (35DCPA) (Gowda et al., 2007a) and other amides (Gowda et al., 2007). The molecular skeleton is essentially planar. The bond parameters in 35DCPCA are similar to those in 2CPCA, 4CPCA, 35DCPA and other acetanilides (Gowda et al., 2007a, b; Gowda et al., 2007). The simultaneous intermolecular N—H···O and N—H···Cl hydrogen bonds (Table 1) link the molecules into chains running along the a axis (Fig. 2).