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

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

doi:10.1107/S1600536808000366

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o420

doi:10.1107/S1600536808000366

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2-Chloro-N-(3,5-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 19 December 2007; accepted 5 January 2008; online 11 January 2008)

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 , 2007a ,b ); Shilpa & Gowda (2007 ).

Experimental

Crystal data

C₈H₆Cl₃NO
M_r = 238.49
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.098
wR(F²) = 0.288
S = 1.39
1730 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −1.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.37	3.019 (4)	133
N1—H1N⋯Cl3ⁱ	0.86	2.68	3.482 (3)	156
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808000366/om2202sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

For related literature, see: Gowda et al. (2007, 2007a,b); 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-(3,5-dichlorophenyl)acetamide top

Crystal data top

C₈H₆Cl₃NO	F(000) = 480
M_r = 238.49	D_x = 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 = 6.2–23.2°
b = 24.350 (4) Å	µ = 8.23 mm⁻¹
c = 8.903 (2) Å	T = 299 K
β = 102.20 (2)°	Long plate, colourless
V = 967.7 (3) Å³	0.60 × 0.35 × 0.13 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.074
Graphite monochromator	θ_max = 66.9°, θ_min = 3.6°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = −29→23
T_min = 0.063, T_max = 0.354	l = −10→10
3732 measured reflections	3 standard reflections every 120 min
1730 independent reflections	intensity decay: 1.0%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.288	H-atom parameters constrained
S = 1.39	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
1730 reflections	(Δ/σ)_max = 0.005
118 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −1.12 e Å⁻³

Crystal data top

C₈H₆Cl₃NO	V = 967.7 (3) Å³
M_r = 238.49	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 4.567 (1) Å	µ = 8.23 mm⁻¹
b = 24.350 (4) Å	T = 299 K
c = 8.903 (2) Å	0.60 × 0.35 × 0.13 mm
β = 102.20 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1606 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.074
T_min = 0.063, T_max = 0.354	3 standard reflections every 120 min
3732 measured reflections	intensity decay: 1.0%
1730 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.098	0 restraints
wR(F²) = 0.288	H-atom parameters constrained
S = 1.39	Δρ_max = 0.57 e Å⁻³
1730 reflections	Δρ_min = −1.12 e Å⁻³
118 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	0.7994 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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 code: (i) x+1/2, −y+1/2, z+1/2.

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)	4.567 (1), 24.350 (4), 8.903 (2)
β (°)	102.20 (2)
V (Å³)	967.7 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	8.23
Crystal size (mm)	0.60 × 0.35 × 0.13

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.063, 0.354
No. of measured, independent and observed [I > 2σ(I)] reflections	3732, 1730, 1606
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.098, 0.288, 1.39
No. of reflections	1730
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −1.12

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	0.86	2.37	3.019 (4)	132.8
N1—H1N···Cl3ⁱ	0.86	2.68	3.482 (3)	156.4

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

Acknowledgements

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

References

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