2-Chloro-N-(3-chloro­phen­yl)acetamide

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

doi:10.1107/S1600536809011660

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o949

doi:10.1107/S1600536809011660

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2-Chloro-N-(3-chlorophenyl)acetamide

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 27 March 2009; accepted 30 March 2009; online 2 April 2009)

The N—H bond in the title compound, C₈H₇Cl₂NO, is anti to the meta-chloro substituent in the aromatic ring in both independent molecules comprising the asymmetric unit. The C=O bond is anti to the N—H bond and is also anti to the methylene H atoms. Intermolecular N—H⋯O hydrogen bonds link the molecules into supramolecular chains.

Related literature

For preparation and characterisation of the compound, see: Pies et al. (1971 ), Gowda et al. (2006 ). For related structures, see: Gowda et al. (2008a ,b ,c ).

Experimental

Crystal data

C₈H₇Cl₂NO
M_r = 204.05
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.897 (1) Å
b = 17.379 (3) Å
c = 21.484 (4) Å
V = 1828.4 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 299 K
0.45 × 0.08 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.756, T_max = 0.987
10213 measured reflections
3179 independent reflections
1745 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.094
wR(F²) = 0.103
S = 1.23
3179 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1206 Friedel pairs
Flack parameter: 0.04 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86	2.15	2.962 (6)	157
N2—H2N⋯O1ⁱⁱ	0.86	2.04	2.892 (6)	174
Symmetry codes: (i) x+1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011660/tk2407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011660/tk2407Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of ring and side-chain substitutions on the solid-state geometry of aromatic amides (Gowda et al., 2008a, b, c), in the present work the structure of 2-chloro-N-(3-chlorophenyl)acetamide (I) has been determined. The N—H bond is anti to the meta-chloro substituent in the aromatic ring (Fig. 1), similar to that observed in N-(3-chlorophenyl)acetamide (Gowda et al., 2008a), but in contrast to the syn conformations observed with respect to the meta-methyl group in 2-chloro-N-(3-methylphenyl)acetamide (Gowda et al., 2008c) and with respect to both chloro substituents in 2-chloro-N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2008b). Further, the C=O bond is not only anti to the N—H bond but also to the methylene-H-atoms. The asymmetric unit of the structure contains two molecules that are orthogonal to each other. The molecules in (I) are linked into infinite chains through intermolecular N1—H1···O2 and N2—H2—O1 hydrogen bonding (Table 1) as viewed down the a-axis (Fig. 2).

Related literature top

For preparation and characterisation of the compound, see: Pies et al. (1971), Gowda et al. (2006). For related structures, see: Gowda et al. (2008a,b,c).

Experimental top

Compound (I) was prepared according to the literature method (Gowda et al., 2006). The purity of (I) was checked by determining its melting point and characterised by recording its infrared, NMR and NQR spectra (Gowda et al., 2006 & Pies et al., 1971). Single crystals of (I) were obtained from an ethanolic solution held at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) viewed in projection down the a-axis, with N-H···O hydrogen bonding shown as dashed lines.

2-Chloro-N-(3-chlorophenyl)acetamide top

Crystal data top

C₈H₇Cl₂NO	F(000) = 832
M_r = 204.05	D_x = 1.483 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2170 reflections
a = 4.897 (1) Å	θ = 2.2–27.3°
b = 17.379 (3) Å	µ = 0.66 mm⁻¹
c = 21.484 (4) Å	T = 299 K
V = 1828.4 (6) Å³	Needle, colourless
Z = 8	0.45 × 0.08 × 0.02 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3179 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.3°, θ_min = 2.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −5→5
T_min = 0.756, T_max = 0.987	k = −20→20
10213 measured reflections	l = −25→23

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)] = 0.094	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0084P)² + 1.6742P] where P = (F_o² + 2F_c²)/3
S = 1.23	(Δ/σ)_max = 0.005
3179 reflections	Δρ_max = 0.36 e Å⁻³
217 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1206 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (13)

Crystal data top

C₈H₇Cl₂NO	V = 1828.4 (6) Å³
M_r = 204.05	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.897 (1) Å	µ = 0.66 mm⁻¹
b = 17.379 (3) Å	T = 299 K
c = 21.484 (4) Å	0.45 × 0.08 × 0.02 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3179 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1745 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.987	R_int = 0.074
10213 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.094	H-atom parameters constrained
wR(F²) = 0.103	Δρ_max = 0.36 e Å⁻³
S = 1.23	Δρ_min = −0.23 e Å⁻³
3179 reflections	Absolute structure: Flack (1983), 1206 Friedel pairs
217 parameters	Absolute structure parameter: 0.04 (13)
0 restraints

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
Cl1	0.6906 (6)	0.02452 (11)	−0.05228 (9)	0.1205 (10)
Cl2	−0.0094 (4)	0.03432 (10)	0.27874 (9)	0.0775 (6)
O1	0.3155 (10)	0.0159 (2)	0.16486 (19)	0.0612 (14)
N1	0.5179 (11)	0.1333 (3)	0.1663 (2)	0.0466 (14)
H1N	0.5335	0.1741	0.1887	0.056*
C1	0.6654 (15)	0.1331 (3)	0.1102 (3)	0.0429 (17)
C2	0.6148 (14)	0.0817 (3)	0.0628 (3)	0.052 (2)
H2	0.4813	0.0441	0.0673	0.063*
C3	0.7641 (19)	0.0868 (4)	0.0088 (3)	0.065 (2)
C4	0.9656 (17)	0.1404 (5)	0.0005 (4)	0.071 (2)
H4	1.0676	0.1422	−0.0360	0.086*
C5	1.0113 (16)	0.1917 (5)	0.0482 (4)	0.076 (2)
H5	1.1442	0.2295	0.0436	0.091*
C6	0.8643 (15)	0.1880 (4)	0.1025 (3)	0.059 (2)
H6	0.8996	0.2229	0.1343	0.071*
C7	0.3544 (15)	0.0775 (4)	0.1898 (3)	0.0451 (18)
C8	0.2235 (15)	0.1014 (3)	0.2507 (3)	0.062 (2)
H8A	0.1310	0.1502	0.2449	0.074*
H8B	0.3655	0.1089	0.2816	0.074*
Cl3	0.3476 (5)	0.13531 (10)	0.41715 (9)	0.0882 (7)
Cl4	−0.7058 (4)	0.32439 (10)	0.17867 (9)	0.0819 (7)
O2	−0.2983 (9)	0.2490 (2)	0.25851 (18)	0.0523 (12)
N2	−0.1818 (11)	0.3561 (2)	0.3135 (2)	0.0484 (14)
H2N	−0.2216	0.4041	0.3169	0.058*
C9	0.0161 (13)	0.3283 (4)	0.3558 (3)	0.0400 (16)
C10	0.0721 (13)	0.2514 (4)	0.3645 (3)	0.0468 (18)
H10	−0.0243	0.2138	0.3430	0.056*
C11	0.2759 (15)	0.2317 (4)	0.4062 (3)	0.0484 (19)
C12	0.4158 (14)	0.2849 (4)	0.4398 (3)	0.058 (2)
H12	0.5517	0.2702	0.4676	0.069*
C13	0.3504 (17)	0.3615 (4)	0.4315 (3)	0.069 (2)
H13	0.4408	0.3989	0.4547	0.083*
C14	0.1548 (16)	0.3833 (4)	0.3897 (3)	0.057 (2)
H14	0.1150	0.4351	0.3841	0.068*
C15	−0.3165 (14)	0.3176 (4)	0.2684 (3)	0.0442 (16)
C16	−0.4892 (14)	0.3714 (3)	0.2297 (3)	0.0599 (19)
H16A	−0.3697	0.4050	0.2061	0.072*
H16B	−0.5973	0.4033	0.2573	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.221 (3)	0.0728 (13)	0.0674 (14)	−0.0099 (18)	0.0240 (19)	−0.0174 (12)
Cl2	0.0703 (15)	0.0686 (12)	0.0935 (15)	−0.0124 (13)	0.0192 (14)	0.0007 (12)
O1	0.089 (4)	0.030 (2)	0.064 (3)	−0.017 (3)	0.007 (3)	−0.011 (2)
N1	0.060 (4)	0.031 (3)	0.049 (4)	−0.009 (3)	0.001 (3)	−0.008 (3)
C1	0.051 (5)	0.031 (4)	0.046 (4)	0.005 (4)	−0.001 (4)	0.000 (4)
C2	0.058 (6)	0.041 (4)	0.058 (5)	0.005 (4)	0.005 (4)	0.006 (4)
C3	0.090 (7)	0.044 (4)	0.061 (5)	0.005 (5)	0.003 (5)	0.008 (4)
C4	0.071 (6)	0.083 (6)	0.061 (6)	0.019 (6)	0.012 (5)	0.013 (5)
C5	0.055 (6)	0.094 (7)	0.080 (6)	−0.016 (5)	0.007 (6)	0.022 (6)
C6	0.047 (5)	0.063 (5)	0.069 (6)	−0.011 (5)	−0.015 (5)	0.004 (4)
C7	0.050 (5)	0.034 (4)	0.051 (4)	−0.001 (4)	−0.012 (4)	0.000 (4)
C8	0.079 (6)	0.047 (4)	0.059 (5)	−0.008 (4)	0.013 (5)	−0.007 (3)
Cl3	0.125 (2)	0.0597 (12)	0.0799 (14)	0.0279 (14)	−0.0236 (14)	0.0066 (11)
Cl4	0.0896 (16)	0.0693 (12)	0.0869 (14)	0.0000 (13)	−0.0394 (13)	−0.0053 (11)
O2	0.061 (3)	0.032 (2)	0.064 (3)	0.006 (3)	−0.012 (3)	−0.009 (2)
N2	0.056 (4)	0.031 (3)	0.058 (4)	0.007 (3)	−0.009 (3)	−0.013 (3)
C9	0.037 (4)	0.043 (4)	0.040 (4)	0.000 (4)	−0.004 (4)	−0.006 (4)
C10	0.053 (5)	0.035 (4)	0.052 (4)	−0.003 (4)	0.002 (4)	−0.001 (3)
C11	0.055 (5)	0.050 (4)	0.040 (4)	0.012 (4)	0.004 (4)	0.005 (3)
C12	0.049 (6)	0.073 (5)	0.051 (5)	0.000 (4)	−0.007 (4)	−0.003 (4)
C13	0.079 (6)	0.061 (5)	0.066 (6)	−0.007 (5)	−0.011 (5)	−0.016 (4)
C14	0.067 (6)	0.049 (4)	0.055 (5)	0.007 (5)	−0.009 (4)	−0.006 (4)
C15	0.046 (4)	0.040 (4)	0.047 (4)	0.010 (4)	−0.004 (4)	−0.001 (4)
C16	0.059 (5)	0.050 (4)	0.071 (5)	−0.001 (4)	−0.029 (5)	−0.011 (4)

Geometric parameters (Å, º) top

Cl1—C3	1.739 (7)	Cl3—C11	1.728 (6)
Cl2—C8	1.738 (6)	Cl4—C16	1.730 (6)
O1—C7	1.212 (6)	O2—C15	1.215 (6)
N1—C7	1.354 (7)	N2—C15	1.349 (7)
N1—C1	1.406 (7)	N2—C9	1.415 (7)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.373 (8)	C9—C10	1.376 (7)
C1—C2	1.376 (7)	C9—C14	1.380 (8)
C2—C3	1.375 (8)	C10—C11	1.384 (8)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.369 (9)	C11—C12	1.359 (8)
C4—C5	1.376 (9)	C12—C13	1.381 (8)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.373 (9)	C13—C14	1.366 (8)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.516 (8)	C15—C16	1.510 (8)
C8—H8A	0.9700	C16—H16A	0.9700
C8—H8B	0.9700	C16—H16B	0.9700

C7—N1—C1	128.4 (5)	C15—N2—C9	128.9 (5)
C7—N1—H1N	115.8	C15—N2—H2N	115.6
C1—N1—H1N	115.8	C9—N2—H2N	115.6
C6—C1—C2	119.3 (6)	C10—C9—C14	120.2 (6)
C6—C1—N1	117.8 (6)	C10—C9—N2	123.7 (6)
C2—C1—N1	122.9 (7)	C14—C9—N2	116.1 (6)
C1—C2—C3	119.1 (7)	C9—C10—C11	118.1 (6)
C1—C2—H2	120.5	C9—C10—H10	120.9
C3—C2—H2	120.5	C11—C10—H10	120.9
C4—C3—C2	122.5 (7)	C12—C11—C10	122.6 (6)
C4—C3—Cl1	118.3 (7)	C12—C11—Cl3	119.0 (6)
C2—C3—Cl1	119.1 (7)	C10—C11—Cl3	118.3 (6)
C3—C4—C5	117.4 (8)	C11—C12—C13	118.1 (7)
C3—C4—H4	121.3	C11—C12—H12	121.0
C5—C4—H4	121.3	C13—C12—H12	121.0
C6—C5—C4	121.2 (8)	C14—C13—C12	120.9 (7)
C6—C5—H5	119.4	C14—C13—H13	119.5
C4—C5—H5	119.4	C12—C13—H13	119.5
C5—C6—C1	120.4 (7)	C13—C14—C9	120.0 (7)
C5—C6—H6	119.8	C13—C14—H14	120.0
C1—C6—H6	119.8	C9—C14—H14	120.0
O1—C7—N1	124.1 (6)	O2—C15—N2	125.2 (6)
O1—C7—C8	123.8 (6)	O2—C15—C16	123.5 (6)
N1—C7—C8	112.1 (5)	N2—C15—C16	111.3 (5)
C7—C8—Cl2	113.2 (4)	C15—C16—Cl4	113.6 (4)
C7—C8—H8A	108.9	C15—C16—H16A	108.8
Cl2—C8—H8A	108.9	Cl4—C16—H16A	108.8
C7—C8—H8B	108.9	C15—C16—H16B	108.8
Cl2—C8—H8B	108.9	Cl4—C16—H16B	108.8
H8A—C8—H8B	107.8	H16A—C16—H16B	107.7

C7—N1—C1—C6	−165.6 (6)	C15—N2—C9—C10	−11.4 (10)
C7—N1—C1—C2	15.7 (10)	C15—N2—C9—C14	169.1 (6)
C6—C1—C2—C3	−0.3 (9)	C14—C9—C10—C11	−2.2 (9)
N1—C1—C2—C3	178.4 (6)	N2—C9—C10—C11	178.3 (5)
C1—C2—C3—C4	1.1 (10)	C9—C10—C11—C12	1.9 (9)
C1—C2—C3—Cl1	−177.3 (5)	C9—C10—C11—Cl3	−179.8 (5)
C2—C3—C4—C5	−1.6 (11)	C10—C11—C12—C13	−0.1 (10)
Cl1—C3—C4—C5	176.8 (6)	Cl3—C11—C12—C13	−178.4 (5)
C3—C4—C5—C6	1.3 (11)	C11—C12—C13—C14	−1.4 (11)
C4—C5—C6—C1	−0.6 (11)	C12—C13—C14—C9	1.1 (11)
C2—C1—C6—C5	0.0 (10)	C10—C9—C14—C13	0.7 (10)
N1—C1—C6—C5	−178.7 (6)	N2—C9—C14—C13	−179.7 (6)
C1—N1—C7—O1	1.8 (10)	C9—N2—C15—O2	3.9 (11)
C1—N1—C7—C8	−177.8 (6)	C9—N2—C15—C16	−174.2 (5)
O1—C7—C8—Cl2	−4.6 (9)	O2—C15—C16—Cl4	10.9 (9)
N1—C7—C8—Cl2	175.0 (4)	N2—C15—C16—Cl4	−170.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.15	2.962 (6)	157
N2—H2N···O1ⁱⁱ	0.86	2.04	2.892 (6)	174

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

Experimental details

Crystal data
Chemical formula	C₈H₇Cl₂NO
M_r	204.05
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	299
a, b, c (Å)	4.897 (1), 17.379 (3), 21.484 (4)
V (Å³)	1828.4 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.45 × 0.08 × 0.02

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.756, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	10213, 3179, 1745
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.094, 0.103, 1.23
No. of reflections	3179
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23
Absolute structure	Flack (1983), 1206 Friedel pairs
Absolute structure parameter	0.04 (13)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.15	2.962 (6)	157
N2—H2N···O1ⁱⁱ	0.86	2.04	2.892 (6)	174

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

References

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Volume 65| Part 5| May 2009| Page o949

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