2-Chloro-N-phenyl­acetamide

Gowda, B.T.; Kožíšek, J.; Tokarčík, M.; Fuess, H.

doi:10.1107/S160053680801266X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o987

doi:10.1107/S160053680801266X

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2-Chloro-N-phenylacetamide

B. Thimme Gowda,^a ^* Jozef Kožíšek,^b Miroslav Tokarčík ^b and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 29 April 2008; accepted 30 April 2008; online 3 May 2008)

In the title compound, C₈H₈ClNO, the conformations of the N—H and C=O bonds are anti to each other, but the C—Cl and C=O bonds in the side chain are syn. The molecules are linked by N—H⋯O hydrogen bonds into infinite chains running in the [101] direction.

Related literature

For the synthesis, see: Gowda et al. (2003 ). For related structures, see: Gowda et al. (2007 , 2008 ).

Experimental

Crystal data

C₈H₈ClNO
M_r = 169.6
Monoclinic, C c
a = 5.0623 (15) Å
b = 18.361 (6) Å
c = 9.115 (2) Å
β = 102.13 (3)°
V = 828.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 297 (2) K
0.41 × 0.24 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 )] T_min = 0.905, T_max = 0.938
2388 measured reflections
1067 independent reflections
385 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.086
S = 0.96
1067 reflections
106 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.1 e Å⁻³
Δρ_min = −0.11 e Å⁻³
Absolute structure: Flack (1983 ), 254 Friedel pairs
Flack parameter: 0.04 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.05	2.848 (5)	155
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801266X/hb2728sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801266X/hb2728Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of the title compoud, (I), 2-chloro-N-(phenyl)-acetamide (NPCA) has been determined, 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., 2007; 2008). The conformations of the N—H and C=O bonds are anti to each other, but the C—Cl and C=O bonds in the side chain are syn to each other (Fig. 1), similar to that observed in 2-chloro-N-(2-chlorophenyl)-acetamide (Gowda et al., 2007)and 2-chloro-N-(3-methylphenyl)-acetamide (Gowda et al., 2008) with similar bond parameters. Further, the amide group –NHCO– in (I) makes a dihedral angle of 16.0 (8)° with the phenyl ring.

Part of the packing for (I) viewed down the b axis is shown in Fig. 2. Infinite chains running along the base vector [101] are formed by N-H···O hydrogen bonds (Table 1).

Related literature top

For the synthesis, see: Gowda et al. (2003). For related structures, see: Gowda et al. (2007, 2008).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003) and colourless prisms of (I) were recrystallised from an ethanol solution.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	Fig. 2. Part of the packing for (I) viewed down the b axis showing the chains arising from N-H···O hydrogen bonds Symmetry code (i): x - 1/2,-y + 1/2,z - 1/2.

2-Chloro-N-phenylacetamide top

Crystal data top

C₈H₈ClNO	F(000) = 352
M_r = 169.6	D_x = 1.36 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 159 reflections
a = 5.0623 (15) Å	θ = 4.9–25.1°
b = 18.361 (6) Å	µ = 0.40 mm⁻¹
c = 9.115 (2) Å	T = 297 K
β = 102.13 (3)°	Prism, colorless
V = 828.3 (4) Å³	0.41 × 0.24 × 0.17 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur System diffractometer	1067 independent reflections
Radiation source: Enhance (Mo) X-ray Source	385 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 10.4340 pixels mm^-1	θ_max = 26°, θ_min = 4.3°
ω scans	h = −6→6
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −22→22
T_min = 0.905, T_max = 0.938	l = −9→11
2388 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.086	[exp(3.70(sinθ/λ)²)]/[σ²(F_o²) + (0.035P)²] where P = 0.33333F_o² + 0.66667F_c²
S = 0.96	(Δ/σ)_max < 0.001
1067 reflections	Δρ_max = 0.1 e Å⁻³
106 parameters	Δρ_min = −0.11 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 254 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (11)

Crystal data top

C₈H₈ClNO	V = 828.3 (4) Å³
M_r = 169.6	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.0623 (15) Å	µ = 0.40 mm⁻¹
b = 18.361 (6) Å	T = 297 K
c = 9.115 (2) Å	0.41 × 0.24 × 0.17 mm
β = 102.13 (3)°

Data collection top

Oxford Diffraction Xcalibur System diffractometer	1067 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	385 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.938	R_int = 0.046
2388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.1 e Å⁻³
S = 0.96	Δρ_min = −0.11 e Å⁻³
1067 reflections	Absolute structure: Flack (1983), 254 Friedel pairs
106 parameters	Absolute structure parameter: 0.04 (11)
2 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	1.3492 (4)	0.15000 (9)	0.9151 (2)	0.1082 (7)
C1	1.0871 (11)	0.1998 (3)	0.8076 (6)	0.0824 (18)
H1A	1.1488	0.2215	0.7237	0.099*
H1B	0.939	0.1671	0.7672	0.099*
C2	0.9849 (11)	0.2595 (3)	0.8961 (6)	0.0629 (17)
N1	0.7939 (8)	0.3008 (2)	0.8086 (4)	0.0642 (13)
H1N	0.7565	0.2897	0.7149	0.077*
O1	1.0653 (7)	0.26846 (19)	1.0314 (3)	0.0833 (13)
C3	0.6481 (10)	0.3597 (3)	0.8507 (6)	0.0517 (13)
C4	0.7302 (11)	0.3975 (3)	0.9862 (6)	0.0670 (17)
H4	0.888	0.3845	1.0536	0.08*
C5	0.5727 (15)	0.4542 (3)	1.0177 (7)	0.082 (2)
H5	0.6222	0.478	1.1094	0.099*
C6	0.3490 (16)	0.4762 (3)	0.9197 (10)	0.0824 (18)
H6	0.2513	0.516	0.9428	0.099*
C7	0.2640 (13)	0.4399 (4)	0.7850 (7)	0.082 (2)
H7	0.1068	0.4538	0.7183	0.099*
C8	0.4153 (10)	0.3835 (4)	0.7525 (6)	0.0676 (16)
H8	0.3614	0.3598	0.6609	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1120 (13)	0.1207 (13)	0.0829 (10)	0.0402 (13)	−0.0004 (9)	0.0083 (13)
C1	0.079 (4)	0.091 (4)	0.067 (4)	0.022 (4)	−0.006 (3)	0.006 (4)
C2	0.070 (4)	0.071 (4)	0.045 (3)	−0.003 (3)	0.005 (3)	0.004 (4)
N1	0.066 (3)	0.084 (3)	0.035 (3)	0.012 (3)	−0.006 (2)	0.003 (3)
O1	0.102 (3)	0.097 (3)	0.039 (2)	0.010 (2)	−0.013 (2)	−0.005 (2)
C3	0.051 (4)	0.062 (4)	0.041 (3)	−0.001 (3)	0.008 (3)	0.002 (3)
C4	0.055 (4)	0.084 (4)	0.059 (4)	0.005 (4)	0.007 (3)	−0.004 (3)
C5	0.083 (5)	0.097 (5)	0.073 (5)	−0.005 (5)	0.029 (4)	−0.014 (4)
C6	0.078 (5)	0.071 (4)	0.101 (5)	0.002 (5)	0.027 (4)	0.005 (5)
C7	0.066 (5)	0.094 (5)	0.081 (5)	0.019 (5)	0.005 (4)	0.020 (5)
C8	0.053 (4)	0.090 (5)	0.058 (4)	0.003 (3)	0.006 (3)	0.014 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.735 (5)	C4—C5	1.378 (7)
C1—C2	1.515 (6)	C4—H4	0.93
C1—H1A	0.97	C5—C6	1.349 (8)
C1—H1B	0.97	C5—H5	0.93
C2—O1	1.226 (6)	C6—C7	1.384 (9)
C2—N1	1.350 (6)	C6—H6	0.93
N1—C3	1.407 (6)	C7—C8	1.357 (7)
N1—H1N	0.86	C7—H7	0.93
C3—C8	1.392 (6)	C8—H8	0.93
C3—C4	1.401 (7)

C2—C1—Cl1	112.8 (4)	C5—C4—C3	118.7 (6)
C2—C1—H1A	109	C5—C4—H4	120.7
Cl1—C1—H1A	109	C3—C4—H4	120.7
C2—C1—H1B	109	C6—C5—C4	122.0 (6)
Cl1—C1—H1B	109	C6—C5—H5	119
H1A—C1—H1B	107.8	C4—C5—H5	119
O1—C2—N1	124.3 (6)	C5—C6—C7	120.3 (6)
O1—C2—C1	123.7 (6)	C5—C6—H6	119.8
N1—C2—C1	112.0 (5)	C7—C6—H6	119.8
C2—N1—C3	128.5 (5)	C8—C7—C6	118.5 (6)
C2—N1—H1N	115.7	C8—C7—H7	120.8
C3—N1—H1N	115.7	C6—C7—H7	120.8
C8—C3—C4	117.8 (5)	C7—C8—C3	122.6 (6)
C8—C3—N1	119.2 (5)	C7—C8—H8	118.7
C4—C3—N1	123.0 (5)	C3—C8—H8	118.7

Cl1—C1—C2—O1	−4.8 (7)	N1—C3—C4—C5	−179.6 (5)
Cl1—C1—C2—N1	175.8 (4)	C3—C4—C5—C6	−2.8 (9)
O1—C2—N1—C3	−1.1 (9)	C4—C5—C6—C7	2.7 (9)
C1—C2—N1—C3	178.3 (5)	C5—C6—C7—C8	−2.0 (9)
C2—N1—C3—C8	−164.2 (5)	C6—C7—C8—C3	1.7 (8)
C2—N1—C3—C4	17.8 (8)	C4—C3—C8—C7	−1.8 (8)
C8—C3—C4—C5	2.3 (8)	N1—C3—C8—C7	−180.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.05	2.848 (5)	155

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

Experimental details

Crystal data
Chemical formula	C₈H₈ClNO
M_r	169.6
Crystal system, space group	Monoclinic, Cc
Temperature (K)	297
a, b, c (Å)	5.0623 (15), 18.361 (6), 9.115 (2)
β (°)	102.13 (3)
V (Å³)	828.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.41 × 0.24 × 0.17

Data collection
Diffractometer	Oxford Diffraction Xcalibur System diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2006), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.905, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	2388, 1067, 385
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.086, 0.96
No. of reflections	1067
No. of parameters	106
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.1, −0.11
Absolute structure	Flack (1983), 254 Friedel pairs
Absolute structure parameter	0.04 (11)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.05	2.848 (5)	155

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

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for the resumption of his research fellowship. JK and MT thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support for the purchase of the diffractometer.

References

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