Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o87
https://doi.org/10.1107/S1600536807062095

2,2-Di­chloro-N-(2,5-di­chloro­phen­yl)acetamide

B. Thimme Gowda,a* Sabine Forob and Hartmut Fuessb

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

The conformation of the N—H bond in the title compound, C8H5Cl4NO, is syn to the 2-chloro substituent and anti to the 5-chloro substituent in the aromatic ring. The bond parameters are similar to those in 2,2-dichloro-N-phenyl­acetamide and other acetanilides. In the crystal structure, the mol­ecules are linked into chains through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2001[Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.], 2006[Gowda, B. T., Paulus, H., Kozisek, J., Tokarcik, M. T. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 675-682.], 2007a[Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2631-o2632.],b[Gowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o3875.],c[Gowda, B. T., Foro, S. & Fuess, H. (2007c). Acta Cryst. E63, o4708.]); Shilpa & Gowda (2007[Shilpa & Gowda, B. T. (2007). Z. Naturforsch. Teil A, 62, 84-90.]).

[Scheme 1]

Experimental

Crystal data

  • C8H5Cl4NO

  • Mr = 272.93

  • Monoclinic, P 21 /c

  • a = 4.6977 (4) Å

  • b = 11.509 (2) Å

  • c = 19.888 (3) Å

  • β = 95.23 (1)°

  • V = 1070.8 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 9.77 mm−1

  • T = 299 (2) K

  • 0.60 × 0.08 × 0.05 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.] Tmin = 0.367, Tmax = 0.591

  • 4168 measured reflections

  • 1917 independent reflections

  • 1420 reflections with I > 2σ(I)

  • Rint = 0.116

  • 3 standard reflections frequency: 120 min intensity decay: 2.0%
Refinement

  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.217

  • S = 1.03

  • 1917 reflections

  • 131 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.72 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.98 (6) 1.90 (6) 2.851 (4) 162 (4)
Symmetry code: (i) x-1, y, z.

Data collection: CAD-4-PC Version (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC Software. Version 1.2. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC Version; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Version 6.2c. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062095/bt2637sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062095/bt2637Isup2.hkl

checkCIF report


Comment top

In the present work, the structure of N-(2,5-dichlorophenyl)-2,2- dichloroacetamide (25DCPDCA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda et al., 2001, 2006; 2007a, b</i, c</i). The conformation of the N—H bond in 25DCPDCA is syn to the 2-chloro substituent and anti to the 5-chloro substituent in the aromatic ring (Fig. 1), in contrast to syn conformation observed with respect to both the 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)-2,2-dichloroacetamide (23DCPDCA) (Gowda et al., 2007c), 2-chloro substituent in N-(2-chlorophenyl)-2,2-dichloroacetamide (2CPDCA)(Gowda et al., 2001), 3-chloro substituent in N-(3,4-dichlorophenyl)-2,2-dichloroacetamide (34DCPDCA)(Gowda et al., 2007b),and 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)-acetamide (23DCPA)(Gowda et al., 2007a), and anti conformation observed with respect to the 3-chloro substituent in the N-(3-chlorophenyl)-2,2-dichloroacetamide (3CPDCA)(Gowda et al., 2006). The bond parameters in 25DCPDCA are similar to those in N-(phenyl)-2,2-dichloroacetamide, 2CPDCA, 3CPDCA, 23DCPDCA, 34DCPDCA, 23DCPA and other acetanilides (Gowda et al., 2001, 2006; 2007a, b</i, b</i). The molecules in 25DCPDCA are linked into chains through N—H···O hydrogen bonding (Table 1 and Fig.2).

Related literature top

For related literature, see: Gowda et al. (2001, 2006, 2007a,b,c); 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.

Refinement top

The H atoms bonded to C were positioned with idealized geometry using a riding model with C—H = 0.93–0.98 Å. The NH atom was located in difference map and its coordinates were refined. Uiso(H) values were set equal to 1.2 Ueq of the parent atom.

Structure description top

In the present work, the structure of N-(2,5-dichlorophenyl)-2,2- dichloroacetamide (25DCPDCA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda et al., 2001, 2006; 2007a, b</i, c</i). The conformation of the N—H bond in 25DCPDCA is syn to the 2-chloro substituent and anti to the 5-chloro substituent in the aromatic ring (Fig. 1), in contrast to syn conformation observed with respect to both the 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)-2,2-dichloroacetamide (23DCPDCA) (Gowda et al., 2007c), 2-chloro substituent in N-(2-chlorophenyl)-2,2-dichloroacetamide (2CPDCA)(Gowda et al., 2001), 3-chloro substituent in N-(3,4-dichlorophenyl)-2,2-dichloroacetamide (34DCPDCA)(Gowda et al., 2007b),and 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)-acetamide (23DCPA)(Gowda et al., 2007a), and anti conformation observed with respect to the 3-chloro substituent in the N-(3-chlorophenyl)-2,2-dichloroacetamide (3CPDCA)(Gowda et al., 2006). The bond parameters in 25DCPDCA are similar to those in N-(phenyl)-2,2-dichloroacetamide, 2CPDCA, 3CPDCA, 23DCPDCA, 34DCPDCA, 23DCPA and other acetanilides (Gowda et al., 2001, 2006; 2007a, b</i, b</i). The molecules in 25DCPDCA are linked into chains through N—H···O hydrogen bonding (Table 1 and Fig.2).

For related literature, see: Gowda et al. (2001, 2006, 2007a,b,c); Shilpa & Gowda (2007).

Computing details top

Data collection: CAD-4-PC Version (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Version (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
[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. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
2,2-Dichloro-N-(2,5-dichlorophenyl)acetamide top
Crystal data top
C8H5Cl4NOF(000) = 544
Mr = 272.93Dx = 1.693 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 4.6977 (4) Åθ = 7.7–20.2°
b = 11.509 (2) ŵ = 9.77 mm−1
c = 19.888 (3) ÅT = 299 K
β = 95.23 (1)°Needle, colourless
V = 1070.8 (3) Å30.60 × 0.08 × 0.05 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		1420 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.116
Graphite monochromatorθmax = 67.0°, θmin = 4.4°
ω/2θ scansh = 0→5
Absorption correction: ψ scan
(North et al., 1968		k = −13→12
Tmin = 0.367, Tmax = 0.591l = −23→23
4168 measured reflections3 standard reflections every 120 min
1917 independent reflections intensity decay: 2.0%
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)] = 0.073H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.217 w = 1/[σ2(Fo2) + (0.144P)2 + 0.518P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.033
1917 reflectionsΔρmax = 0.80 e Å−3
131 parametersΔρmin = −0.72 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (10)
Crystal data top
C8H5Cl4NOV = 1070.8 (3) Å3
Mr = 272.93Z = 4
Monoclinic, P21/cCu Kα radiation
a = 4.6977 (4) ŵ = 9.77 mm−1
b = 11.509 (2) ÅT = 299 K
c = 19.888 (3) Å0.60 × 0.08 × 0.05 mm
β = 95.23 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1420 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968		Rint = 0.116
Tmin = 0.367, Tmax = 0.5913 standard reflections every 120 min
4168 measured reflections intensity decay: 2.0%
1917 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0730 restraints
wR(F2) = 0.217H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.80 e Å−3
1917 reflectionsΔρmin = −0.72 e Å−3
131 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
xyzUiso*/Ueq
C10.3994 (8)0.7062 (3)0.43590 (17)0.0324 (8)
C20.2953 (8)0.8112 (3)0.45736 (19)0.0367 (8)
C30.3981 (10)0.8573 (3)0.5194 (2)0.0439 (10)
H30.32560.92730.53370.053*
C40.6063 (10)0.8001 (4)0.55998 (19)0.0440 (9)
H40.67640.83130.60140.053*
C50.7093 (9)0.6956 (4)0.53810 (19)0.0389 (9)
C60.6085 (8)0.6475 (3)0.47678 (18)0.0345 (8)
H60.67970.57680.46300.041*
C70.4478 (8)0.6066 (3)0.33005 (18)0.0344 (8)
C80.2734 (8)0.5542 (4)0.26817 (19)0.0411 (9)
H80.09320.52380.28220.049*
N10.2888 (7)0.6573 (3)0.37354 (16)0.0379 (7)
H1N0.080 (12)0.653 (4)0.365 (2)0.045*
O10.7058 (6)0.5995 (4)0.33605 (15)0.0578 (10)
Cl10.0411 (3)0.88522 (9)0.40600 (6)0.0526 (4)
Cl20.9670 (3)0.62104 (10)0.58918 (5)0.0529 (4)
Cl30.4607 (4)0.4414 (2)0.23486 (12)0.1290 (11)
Cl40.1977 (5)0.66320 (18)0.20858 (7)0.0964 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0219 (16)0.0374 (17)0.0371 (17)−0.0020 (15)−0.0014 (13)−0.0001 (14)
C20.0262 (18)0.0368 (18)0.047 (2)0.0029 (15)0.0014 (15)0.0014 (15)
C30.043 (2)0.0387 (19)0.050 (2)0.0025 (19)0.0064 (19)−0.0080 (17)
C40.044 (2)0.049 (2)0.0380 (19)−0.002 (2)−0.0037 (17)−0.0059 (16)
C50.0312 (19)0.046 (2)0.0383 (18)−0.0034 (17)−0.0028 (15)0.0030 (15)
C60.0234 (18)0.0380 (17)0.0415 (19)0.0014 (16)0.0002 (15)−0.0038 (15)
C70.0174 (17)0.0484 (19)0.0366 (18)−0.0005 (15)−0.0015 (14)−0.0015 (15)
C80.0202 (17)0.059 (2)0.0424 (19)−0.0010 (18)−0.0059 (15)−0.0060 (18)
N10.0157 (14)0.0525 (17)0.0442 (17)0.0034 (15)−0.0044 (12)−0.0095 (14)
O10.0155 (14)0.104 (3)0.0529 (18)0.0009 (16)−0.0025 (12)−0.0211 (16)
Cl10.0420 (7)0.0528 (6)0.0619 (7)0.0160 (5)−0.0019 (5)0.0066 (4)
Cl20.0484 (7)0.0613 (7)0.0456 (6)0.0052 (5)−0.0138 (5)0.0056 (4)
Cl30.0671 (10)0.1554 (19)0.1553 (17)0.0449 (12)−0.0398 (11)−0.1137 (16)
Cl40.1098 (15)0.1129 (13)0.0588 (9)−0.0326 (12)−0.0344 (9)0.0310 (8)
Geometric parameters (Å, º) top
C1—C21.386 (5)C5—Cl21.735 (4)
C1—C61.392 (5)C6—H60.9300
C1—N11.417 (5)C7—O11.209 (5)
C2—C31.389 (6)C7—N11.328 (5)
C2—Cl11.724 (4)C7—C81.538 (5)
C3—C41.377 (6)C8—Cl31.734 (4)
C3—H30.9300C8—Cl41.740 (4)
C4—C51.381 (6)C8—H80.9800
C4—H40.9300N1—H1N0.98 (6)
C5—C61.383 (5)
C2—C1—C6119.6 (3)C5—C6—C1119.2 (3)
C2—C1—N1120.3 (3)C5—C6—H6120.4
C6—C1—N1120.1 (3)C1—C6—H6120.4
C1—C2—C3120.2 (4)O1—C7—N1125.7 (4)
C1—C2—Cl1119.6 (3)O1—C7—C8120.5 (4)
C3—C2—Cl1120.2 (3)N1—C7—C8113.8 (3)
C4—C3—C2120.6 (4)C7—C8—Cl3110.3 (3)
C4—C3—H3119.7C7—C8—Cl4108.9 (3)
C2—C3—H3119.7Cl3—C8—Cl4111.0 (2)
C3—C4—C5118.8 (4)C7—C8—H8108.9
C3—C4—H4120.6Cl3—C8—H8108.9
C5—C4—H4120.6Cl4—C8—H8108.9
C4—C5—C6121.7 (4)C7—N1—C1124.1 (3)
C4—C5—Cl2119.5 (3)C7—N1—H1N119 (3)
C6—C5—Cl2118.9 (3)C1—N1—H1N117 (3)
C6—C1—C2—C3−0.3 (6)C2—C1—C6—C5−0.2 (6)
N1—C1—C2—C3178.1 (4)N1—C1—C6—C5−178.7 (3)
C6—C1—C2—Cl1178.8 (3)O1—C7—C8—Cl325.6 (5)
N1—C1—C2—Cl1−2.8 (5)N1—C7—C8—Cl3−154.3 (3)
C1—C2—C3—C40.7 (6)O1—C7—C8—Cl4−96.5 (4)
Cl1—C2—C3—C4−178.3 (3)N1—C7—C8—Cl483.6 (4)
C2—C3—C4—C5−0.6 (7)O1—C7—N1—C1−3.3 (7)
C3—C4—C5—C60.0 (7)C8—C7—N1—C1176.5 (3)
C3—C4—C5—Cl2−178.8 (3)C2—C1—N1—C7138.6 (4)
C4—C5—C6—C10.4 (6)C6—C1—N1—C7−43.0 (6)
Cl2—C5—C6—C1179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.98 (6)1.90 (6)2.851 (4)162 (4)
Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC8H5Cl4NO
Mr272.93
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)4.6977 (4), 11.509 (2), 19.888 (3)
β (°) 95.23 (1)
V (Å3)1070.8 (3)
Z4
Radiation typeCu Kα
µ (mm−1)9.77
Crystal size (mm)0.60 × 0.08 × 0.05
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968
Tmin, Tmax0.367, 0.591
No. of measured, independent and
observed [I > 2σ(I)] reflections		4168, 1917, 1420
Rint0.116
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.217, 1.03
No. of reflections1917
No. of parameters131
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.80, −0.72

Computer programs: CAD-4-PC Version (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.98 (6)1.90 (6)2.851 (4)162 (4)
Symmetry code: (i) x−1, y, z.
 

Acknowledgements

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

References

First citationEnraf–Nonius (1996). CAD-4-PC Software. Version 1.2. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2631–o2632.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o3875.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007c). Acta Cryst. E63, o4708.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386–394.  CAS Google Scholar
 First citationGowda, B. T., Paulus, H., Kozisek, J., Tokarcik, M. T. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 675–682.  CAS Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationShilpa & Gowda, B. T. (2007). Z. Naturforsch. Teil A, 62, 84–90.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (1987). REDU4. Version 6.2c. Stoe & Cie GmbH, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o87
https://doi.org/10.1107/S1600536807062095
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS