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

Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536808000408

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o419

doi:10.1107/S1600536808000408

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

B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^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 18 December 2007; accepted 6 January 2008; online 11 January 2008)

The conformation of the N—H bond in the title compound (23DCPCA), C₈H₆Cl₃NO, is syn to both the 2- and 3-chloro substituents in the aromatic ring, similar to the 2-chloro substituent in 2-chloro-N-(2-chlorophenyl)acetamide (2CPCA), the 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)acetamide (23DCPA) and in 2,2-dichloro-N-(2,3-dichlorophenyl)acetamide (23DCPDCA). The bond parameters in 23DCPCA are similar to those in 2-chloro-N-(phenyl)acetamide, 2CPCA, 23DCPA, 23DCPDCA and other acetanilides. The molecules in 23DCPCA are linked into chains through N—H⋯O hydrogen bonding.

Related literature

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

Experimental

Crystal data

C₈H₆Cl₃NO
M_r = 238.49
Monoclinic, P 2₁ /n
a = 11.704 (3) Å
b = 4.712 (1) Å
c = 17.503 (4) Å
β = 99.76 (2)°
V = 951.3 (4) Å³
Z = 4
Cu Kα radiation
μ = 8.38 mm⁻¹
T = 299 (2) K
0.50 × 0.35 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.014, T_max = 0.096
1832 measured reflections
1692 independent reflections
1625 reflections with I > 2σ(I)
R_int = 0.036
3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.231
S = 1.07
1692 reflections
122 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.87 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.85 (5)	2.05 (5)	2.862 (4)	161 (4)
Symmetry code: (i) x, y-1, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000408/om2201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000408/om2201Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(2,3-dichlorophenyl)- acetamide (23DCPCA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda et al., 2007a, b, c). The conformation of the N—H bond in 23DCPCA is syn to both the 2-chloro and 3-chloro substituent (Fig. 1), similar to that of 2-chloro substituent in 2-chloro-N-(2-chlorophenyl)acetamide (2CPCA)(Gowda et al., 2007b), 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)-acetamide (23DCPA) (Gowda et al., 2007a) and in 2,2-dichloro-N-(2,3-dichlorophenyl)acetamide (23DCPDCA)(Gowda et al., 2007c). The bond parameters in 23DCPCA are similar to those in 2-chloro-N-(phenyl)acetamide, 2CPCA, 23DCPA, 23DCPDCA and other acetanilides (Gowda et al., 2007a, b, c). The molecules in the structure of 23DCPCA are stabilized through N—H···O hydrogen bonding (Table 1 and Fig.2).

Related literature top

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

Experimental top

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.

Computing details top

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).

Figures top

	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.

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

Crystal data top

C₈H₆Cl₃NO	F(000) = 480
M_r = 238.49	D_x = 1.665 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.704 (3) Å	θ = 4.3–23.9°
b = 4.712 (1) Å	µ = 8.38 mm⁻¹
c = 17.503 (4) Å	T = 299 K
β = 99.76 (2)°	Prism, colourless
V = 951.3 (4) Å³	0.50 × 0.35 × 0.28 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1625 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 66.9°, θ_min = 4.2°
ω/2θ scans	h = −13→1
Absorption correction: ψ scan (North et al., 1968)	k = −5→0
T_min = 0.014, T_max = 0.096	l = −20→20
1832 measured reflections	3 standard reflections every 120 min
1692 independent reflections	intensity decay: 2.0%

Refinement top

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)] = 0.080	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.231	w = 1/[σ²(F_o²) + (0.181P)² + 0.9328P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.025
1692 reflections	Δρ_max = 0.87 e Å⁻³
122 parameters	Δρ_min = −1.04 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Crystal data top

C₈H₆Cl₃NO	V = 951.3 (4) Å³
M_r = 238.49	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.704 (3) Å	µ = 8.38 mm⁻¹
b = 4.712 (1) Å	T = 299 K
c = 17.503 (4) Å	0.50 × 0.35 × 0.28 mm
β = 99.76 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1625 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.036
T_min = 0.014, T_max = 0.096	3 standard reflections every 120 min
1832 measured reflections	intensity decay: 2.0%
1692 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.87 e Å⁻³
1692 reflections	Δρ_min = −1.04 e Å⁻³
122 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

	x	y	z	U_iso*/U_eq
C1	0.4488 (3)	0.5307 (7)	0.36495 (19)	0.0315 (8)
C2	0.4556 (3)	0.4122 (7)	0.2935 (2)	0.0316 (8)
C3	0.5442 (3)	0.4955 (9)	0.2544 (2)	0.0395 (9)
C4	0.6240 (4)	0.6936 (10)	0.2854 (3)	0.0502 (11)
H4	0.6825	0.7486	0.2586	0.060*
C5	0.6172 (4)	0.8099 (9)	0.3558 (3)	0.0502 (11)
H5	0.6714	0.9453	0.3768	0.060*
C6	0.5313 (3)	0.7298 (9)	0.3964 (2)	0.0416 (9)
H6	0.5284	0.8089	0.4447	0.050*
C7	0.2947 (4)	0.6252 (8)	0.4390 (2)	0.0376 (9)
C8	0.1935 (4)	0.4823 (8)	0.4667 (2)	0.0430 (10)
H8A	0.2178	0.2983	0.4884	0.052*
H8B	0.1320	0.4519	0.4228	0.052*
N1	0.3582 (3)	0.4477 (7)	0.40382 (17)	0.0347 (8)
H1N	0.346 (4)	0.271 (11)	0.405 (3)	0.042*
O1	0.3132 (3)	0.8774 (6)	0.4466 (2)	0.0556 (9)
Cl1	0.35541 (7)	0.16288 (19)	0.25447 (5)	0.0389 (5)
Cl2	0.55325 (12)	0.3482 (3)	0.16544 (7)	0.0653 (6)
Cl3	0.14026 (11)	0.6855 (3)	0.53663 (7)	0.0602 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0320 (17)	0.0313 (17)	0.0342 (16)	−0.0005 (13)	0.0143 (13)	0.0009 (13)
C2	0.0245 (16)	0.0345 (17)	0.0383 (18)	−0.0019 (13)	0.0126 (13)	0.0041 (14)
C3	0.0316 (17)	0.050 (2)	0.0428 (19)	0.0012 (16)	0.0234 (14)	0.0043 (16)
C4	0.034 (2)	0.056 (2)	0.067 (3)	−0.0074 (17)	0.0248 (19)	0.006 (2)
C5	0.033 (2)	0.049 (2)	0.070 (3)	−0.0125 (17)	0.0109 (19)	−0.0012 (19)
C6	0.040 (2)	0.045 (2)	0.042 (2)	−0.0058 (16)	0.0097 (16)	−0.0031 (16)
C7	0.050 (2)	0.0314 (18)	0.0354 (18)	−0.0010 (15)	0.0188 (16)	0.0010 (14)
C8	0.048 (2)	0.040 (2)	0.049 (2)	−0.0055 (16)	0.0304 (17)	−0.0054 (16)
N1	0.0431 (16)	0.0293 (15)	0.0376 (16)	−0.0022 (12)	0.0236 (13)	−0.0005 (12)
O1	0.074 (2)	0.0305 (15)	0.076 (2)	−0.0035 (13)	0.0499 (18)	−0.0054 (13)
Cl1	0.0360 (7)	0.0433 (7)	0.0411 (7)	−0.0057 (3)	0.0170 (4)	−0.0078 (3)
Cl2	0.0670 (9)	0.0878 (10)	0.0529 (8)	−0.0123 (6)	0.0438 (6)	−0.0074 (5)
Cl3	0.0646 (9)	0.0640 (9)	0.0639 (8)	−0.0105 (5)	0.0454 (6)	−0.0179 (5)

Geometric parameters (Å, º) top

C1—C2	1.384 (5)	C5—H5	0.9300
C1—C6	1.391 (5)	C6—H6	0.9300
C1—N1	1.409 (4)	C7—O1	1.211 (5)
C2—C3	1.392 (5)	C7—N1	1.337 (5)
C2—Cl1	1.718 (3)	C7—C8	1.512 (5)
C3—C4	1.366 (6)	C8—Cl3	1.750 (4)
C3—Cl2	1.725 (4)	C8—H8A	0.9700
C4—C5	1.363 (7)	C8—H8B	0.9700
C4—H4	0.9300	N1—H1N	0.85 (5)
C5—C6	1.379 (6)

C2—C1—C6	119.2 (3)	C5—C6—C1	119.9 (4)
C2—C1—N1	119.2 (3)	C5—C6—H6	120.0
C6—C1—N1	121.7 (3)	C1—C6—H6	120.0
C1—C2—C3	119.5 (3)	O1—C7—N1	124.2 (4)
C1—C2—Cl1	119.7 (3)	O1—C7—C8	122.5 (4)
C3—C2—Cl1	120.8 (3)	N1—C7—C8	113.3 (3)
C4—C3—C2	120.9 (4)	C7—C8—Cl3	111.8 (3)
C4—C3—Cl2	119.4 (3)	C7—C8—H8A	109.3
C2—C3—Cl2	119.7 (3)	Cl3—C8—H8A	109.3
C5—C4—C3	119.5 (4)	C7—C8—H8B	109.3
C5—C4—H4	120.2	Cl3—C8—H8B	109.3
C3—C4—H4	120.2	H8A—C8—H8B	107.9
C4—C5—C6	121.0 (4)	C7—N1—C1	124.9 (3)
C4—C5—H5	119.5	C7—N1—H1N	119 (3)
C6—C5—H5	119.5	C1—N1—H1N	116 (3)

C6—C1—C2—C3	−0.3 (5)	C3—C4—C5—C6	0.2 (7)
N1—C1—C2—C3	179.3 (3)	C4—C5—C6—C1	−1.0 (7)
C6—C1—C2—Cl1	179.3 (3)	C2—C1—C6—C5	1.0 (6)
N1—C1—C2—Cl1	−1.1 (5)	N1—C1—C6—C5	−178.6 (4)
C1—C2—C3—C4	−0.4 (6)	O1—C7—C8—Cl3	−20.3 (5)
Cl1—C2—C3—C4	−180.0 (3)	N1—C7—C8—Cl3	161.7 (3)
C1—C2—C3—Cl2	179.9 (3)	O1—C7—N1—C1	−5.7 (6)
Cl1—C2—C3—Cl2	0.3 (5)	C8—C7—N1—C1	172.3 (3)
C2—C3—C4—C5	0.4 (6)	C2—C1—N1—C7	−135.6 (4)
Cl2—C3—C4—C5	−179.9 (3)	C6—C1—N1—C7	44.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (5)	2.05 (5)	2.862 (4)	161 (4)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₈H₆Cl₃NO
M_r	238.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	11.704 (3), 4.712 (1), 17.503 (4)
β (°)	99.76 (2)
V (Å³)	951.3 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	8.38
Crystal size (mm)	0.50 × 0.35 × 0.28

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.014, 0.096
No. of measured, independent and observed [I > 2σ(I)] reflections	1832, 1692, 1625
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.231, 1.07
No. of reflections	1692
No. of parameters	122
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.87, −1.04

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (5)	2.05 (5)	2.862 (4)	161 (4)

Symmetry code: (i) x, y−1, z.

Acknowledgements

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

References

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