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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o420.
Published online 2008 January 11. doi:  10.1107/S1600536808000366
PMCID: PMC2960189

2-Chloro-N-(3,5-dichloro­phen­yl)acetamide

Abstract

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—H(...)Cl inter­molecular hydrogen bonds running along the a axis

Related literature

For related literature, see: Gowda et al. (2007 [triangle], 2007a [triangle],b [triangle]); Shilpa & Gowda (2007 [triangle]).

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Object name is e-64-0o420-scheme1.jpg

Experimental

Crystal data

  • C8H6Cl3NO
  • M r = 238.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o420-efi1.jpg
  • a = 4.567 (1) Å
  • b = 24.350 (4) Å
  • c = 8.903 (2) Å
  • β = 102.20 (2)°
  • V = 967.7 (3) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 8.23 mm−1
  • T = 299 (2) K
  • 0.60 × 0.35 × 0.13 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.063, T max = 0.354
  • 3732 measured reflections
  • 1730 independent reflections
  • 1606 reflections with I > 2σ(I)
  • R int = 0.073
  • 3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.098
  • wR(F 2) = 0.288
  • S = 1.39
  • 1730 reflections
  • 118 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −1.12 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000366/om2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000366/om2202Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Crystal data

C8H6Cl3NOF000 = 480
Mr = 238.49Dx = 1.637 Mg m3
Monoclinic, P21/nCu Kα radiation λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 4.567 (1) Åθ = 6.2–23.2º
b = 24.350 (4) ŵ = 8.23 mm1
c = 8.903 (2) ÅT = 299 (2) K
β = 102.20 (2)ºLong plate, colourless
V = 967.7 (3) Å30.60 × 0.35 × 0.13 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.074
Radiation source: fine-focus sealed tubeθmax = 66.9º
Monochromator: graphiteθmin = 3.6º
T = 299(2) Kh = 0→5
ω/2θ scansk = −29→23
Absorption correction: ψ scan(North et al., 1968)l = −10→10
Tmin = 0.063, Tmax = 0.3543 standard reflections
3732 measured reflections every 120 min
1730 independent reflections intensity decay: 1.0%
1606 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.098H-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 reflectionsΔρmax = 0.57 e Å3
118 parametersΔρmin = −1.12 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
C10.7994 (8)0.15227 (14)0.4676 (4)0.0509 (8)
C20.9691 (7)0.12475 (16)0.5925 (4)0.0528 (9)
H20.96170.13530.69210.063*
C31.1486 (9)0.08169 (15)0.5677 (5)0.0585 (10)
C41.1657 (10)0.06515 (16)0.4216 (5)0.0639 (10)
H41.28840.03620.40590.077*
C50.9960 (10)0.09289 (17)0.3011 (5)0.0615 (10)
C60.8060 (8)0.13604 (15)0.3183 (4)0.0553 (9)
H60.68810.15330.23360.066*
C70.4446 (7)0.23062 (14)0.4049 (4)0.0466 (8)
C80.3181 (8)0.27475 (16)0.4947 (4)0.0539 (9)
H8A0.47870.29920.54250.065*
H8B0.23880.25750.57580.065*
N10.6266 (7)0.19666 (13)0.5008 (3)0.0513 (8)
H1N0.63940.20300.59700.062*
O10.3874 (5)0.22828 (12)0.2651 (3)0.0560 (8)
Cl11.3597 (3)0.04771 (4)0.72484 (15)0.0797 (6)
Cl21.0161 (4)0.07364 (6)0.11529 (14)0.0948 (6)
Cl30.0336 (2)0.31342 (4)0.37802 (10)0.0626 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0514 (16)0.0467 (17)0.0520 (18)−0.0028 (13)0.0048 (14)0.0006 (14)
C20.0540 (19)0.0512 (18)0.0503 (18)−0.0072 (14)0.0042 (14)−0.0012 (14)
C30.057 (2)0.0451 (17)0.068 (2)−0.0029 (14)−0.0001 (17)0.0021 (16)
C40.073 (2)0.0481 (17)0.071 (2)0.0086 (17)0.0157 (19)−0.0015 (18)
C50.073 (2)0.055 (2)0.059 (2)−0.0001 (16)0.0189 (17)−0.0056 (16)
C60.064 (2)0.0501 (19)0.051 (2)−0.0011 (15)0.0115 (16)−0.0001 (15)
C70.0435 (15)0.0520 (17)0.0421 (16)−0.0029 (13)0.0038 (12)0.0003 (13)
C80.0540 (18)0.062 (2)0.0406 (17)0.0106 (15)−0.0004 (13)−0.0021 (14)
N10.0544 (15)0.0573 (16)0.0382 (14)0.0062 (12)0.0010 (12)−0.0012 (12)
O10.0566 (14)0.0654 (16)0.0413 (13)0.0070 (11)−0.0002 (10)−0.0017 (11)
Cl10.0871 (9)0.0616 (8)0.0782 (9)0.0179 (5)−0.0100 (7)0.0057 (5)
Cl20.1422 (14)0.0816 (10)0.0661 (9)0.0296 (7)0.0342 (8)−0.0070 (6)
Cl30.0580 (7)0.0717 (8)0.0538 (8)0.0174 (4)0.0023 (5)0.0058 (4)

Geometric parameters (Å, °)

C1—C21.387 (5)C5—Cl21.740 (4)
C1—C61.393 (5)C6—H60.9300
C1—N11.406 (5)C7—O11.218 (4)
C2—C31.377 (5)C7—N11.343 (5)
C2—H20.9300C7—C81.524 (5)
C3—C41.380 (6)C8—Cl31.756 (3)
C3—Cl11.732 (4)C8—H8A0.9700
C4—C51.363 (6)C8—H8B0.9700
C4—H40.9300N1—H1N0.8600
C5—C61.392 (5)
C2—C1—C6120.5 (3)C5—C6—C1117.3 (3)
C2—C1—N1116.5 (3)C5—C6—H6121.3
C6—C1—N1123.0 (3)C1—C6—H6121.3
C3—C2—C1119.3 (3)O1—C7—N1126.2 (3)
C3—C2—H2120.3O1—C7—C8123.1 (3)
C1—C2—H2120.3N1—C7—C8110.7 (3)
C2—C3—C4121.9 (3)C7—C8—Cl3112.5 (2)
C2—C3—Cl1118.9 (3)C7—C8—H8A109.1
C4—C3—Cl1119.3 (3)Cl3—C8—H8A109.1
C5—C4—C3117.5 (4)C7—C8—H8B109.1
C5—C4—H4121.3Cl3—C8—H8B109.1
C3—C4—H4121.3H8A—C8—H8B107.8
C4—C5—C6123.5 (3)C7—N1—C1129.7 (3)
C4—C5—Cl2118.6 (3)C7—N1—H1N115.1
C6—C5—Cl2117.9 (3)C1—N1—H1N115.1
C6—C1—C2—C31.1 (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—C40.3 (6)N1—C1—C6—C5177.4 (3)
C1—C2—C3—Cl1179.9 (3)O1—C7—C8—Cl310.7 (5)
C2—C3—C4—C5−0.4 (6)N1—C7—C8—Cl3−170.4 (3)
Cl1—C3—C4—C5179.9 (3)O1—C7—N1—C12.0 (6)
C3—C4—C5—C6−0.9 (6)C8—C7—N1—C1−176.8 (3)
C3—C4—C5—Cl2179.2 (3)C2—C1—N1—C7179.5 (3)
C4—C5—C6—C12.1 (6)C6—C1—N1—C70.0 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.373.019 (4)133
N1—H1N···Cl3i0.862.683.482 (3)156

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2202).

References

  • 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.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography