2-Chloro-N-phenyl-acetamide.

In the title compound, C(8)H(8)ClNO, 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 mol-ecules 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 = 169.6

Monoclinic,

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 ▶), 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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.086

S = 0.96

1067 reflections

106 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.1 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack (1983 ▶), 254 Friedel pairs

Flack parameter: 0.04 (11)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H8ClNO	F000 = 352
Mr = 169.6	Dx = 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 = 4.9–25.1º
b = 18.361 (6) Å	µ = 0.40 mm−1
c = 9.115 (2) Å	T = 297 (2) K
β = 102.13 (3)º	Prism, colorless
V = 828.3 (4) Å3	0.41 × 0.24 × 0.17 mm
Z = 4

Oxford Diffraction Xcalibur System diffractometer	1067 independent reflections
Radiation source: Enhance (Mo) X-ray Source	385 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
Detector resolution: 10.4340 pixels mm-1	θmax = 26º
T = 297(2) K	θmin = 4.3º
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
Tmin = 0.905, Tmax = 0.938	l = −9→11
2388 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	[exp(3.70(sinθ/λ)2)]/[σ2(Fo2) + (0.035P)2] where P = 0.33333Fo2 + 0.66667Fc2
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.1 e Å−3
1067 reflections	Δρmin = −0.11 e Å−3
106 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 254 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (11)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .