2-(4-Chloro-phen-yl)acetamide.

In the title compound, C(8)H(8)ClNO, the acetamide group is twisted out the benzene plane with a dihedral angle of 83.08 (1)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming layers parallel to the ab plane.

Related literature

For details of the nitrile hydrolysis of the same substrate (4-chlorobenzonitrile) by another method, see: Moorthy & Singhal (2005 ▶).

Experimental

Crystal data

C8H8ClNO

M = 169.60

Orthorhombic,

a = 4.917 (2) Å

b = 6.033 (4) Å

c = 26.680 (12) Å

V = 791.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.29 × 0.22 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.887, T max = 0.970

7733 measured reflections

1807 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.083

S = 1.05

1807 reflections

108 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 704 Friedel pairs

Flack parameter: −0.12 (8)

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046836/cv5191sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046836/cv5191Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046836/cv5191Isup3.cml

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

C8H8ClNO	F(000) = 352
Mr = 169.60	Dx = 1.423 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5994 reflections
a = 4.917 (2) Å	θ = 3.1–27.4°
b = 6.033 (4) Å	µ = 0.42 mm−1
c = 26.680 (12) Å	T = 293 K
V = 791.5 (7) Å3	Block, colorless
Z = 4	0.29 × 0.22 × 0.07 mm

Rigaku R-AXIS RAPID diffractometer	1807 independent reflections
Radiation source: fine-focus sealed tube	1451 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scan	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.887, Tmax = 0.970	k = −7→7
7733 measured reflections	l = −34→33

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.036P)2 + 0.1017P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1807 reflections	Δρmax = 0.17 e Å−3
108 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack (1983), 704 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.12 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.3632 (4)	0.5073 (3)	0.79843 (7)	0.0335 (4)
C2	0.2527 (4)	0.3677 (5)	0.84087 (10)	0.0603 (7)
H2A	0.1560	0.4638	0.8639	0.072*
H2B	0.1222	0.2633	0.8272	0.072*
C3	0.4640 (4)	0.2408 (4)	0.86973 (8)	0.0429 (5)
C4	0.5575 (5)	0.0374 (4)	0.85279 (8)	0.0487 (6)
H4	0.4907	−0.0195	0.8228	0.058*
C5	0.7475 (5)	−0.0822 (3)	0.87944 (8)	0.0451 (5)
H5	0.8079	−0.2185	0.8676	0.054*
C6	0.8470 (4)	0.0017 (4)	0.92375 (8)	0.0410 (5)
C7	0.7620 (5)	0.2049 (4)	0.94146 (8)	0.0472 (6)
H7	0.8324	0.2622	0.9711	0.057*
C8	0.5697 (5)	0.3221 (4)	0.91430 (8)	0.0487 (5)
H8	0.5100	0.4586	0.9262	0.058*
Cl1	1.08553 (13)	−0.14906 (11)	0.95804 (2)	0.0605 (2)
N1	0.1788 (3)	0.6234 (4)	0.77353 (7)	0.0441 (4)
H11	0.004 (2)	0.613 (4)	0.7811 (8)	0.046 (6)*
H12	0.225 (5)	0.714 (4)	0.7485 (7)	0.064 (8)*
O1	0.6073 (3)	0.5149 (3)	0.78808 (5)	0.0435 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0263 (9)	0.0376 (11)	0.0367 (10)	−0.0005 (9)	0.0007 (8)	−0.0027 (8)
C2	0.0291 (11)	0.0819 (19)	0.0699 (15)	0.0050 (12)	0.0050 (11)	0.0347 (15)
C3	0.0310 (11)	0.0528 (13)	0.0449 (11)	0.0000 (9)	0.0035 (9)	0.0145 (9)
C4	0.0493 (13)	0.0554 (14)	0.0416 (11)	−0.0093 (12)	−0.0077 (11)	−0.0001 (10)
C5	0.0511 (13)	0.0368 (12)	0.0475 (12)	0.0016 (9)	0.0072 (11)	−0.0041 (9)
C6	0.0381 (11)	0.0444 (12)	0.0406 (10)	0.0018 (10)	0.0046 (9)	0.0071 (9)
C7	0.0514 (13)	0.0514 (14)	0.0387 (11)	0.0009 (10)	−0.0027 (10)	−0.0056 (10)
C8	0.0503 (13)	0.0433 (13)	0.0525 (12)	0.0118 (12)	0.0069 (12)	−0.0003 (10)
Cl1	0.0520 (3)	0.0695 (4)	0.0598 (3)	0.0147 (3)	−0.0015 (3)	0.0194 (3)
N1	0.0243 (8)	0.0587 (12)	0.0494 (10)	−0.0006 (8)	0.0013 (8)	0.0149 (10)
O1	0.0237 (6)	0.0529 (9)	0.0538 (8)	−0.0038 (7)	0.0051 (7)	0.0046 (7)

C1—O1	1.232 (2)	C5—C6	1.376 (3)
C1—N1	1.324 (3)	C5—H5	0.9300
C1—C2	1.512 (3)	C6—C7	1.379 (3)
C2—C3	1.503 (3)	C6—Cl1	1.744 (2)
C2—H2A	0.9700	C7—C8	1.386 (3)
C2—H2B	0.9700	C7—H7	0.9300
C3—C4	1.386 (3)	C8—H8	0.9300
C3—C8	1.387 (3)	N1—H11	0.883 (10)
C4—C5	1.378 (3)	N1—H12	0.892 (10)
C4—H4	0.9300
O1—C1—N1	122.34 (19)	C6—C5—C4	119.5 (2)
O1—C1—C2	122.57 (18)	C6—C5—H5	120.3
N1—C1—C2	115.08 (17)	C4—C5—H5	120.3
C3—C2—C1	114.78 (17)	C5—C6—C7	120.9 (2)
C3—C2—H2A	108.6	C5—C6—Cl1	119.88 (18)
C1—C2—H2A	108.6	C7—C6—Cl1	119.21 (17)
C3—C2—H2B	108.6	C6—C7—C8	118.8 (2)
C1—C2—H2B	108.6	C6—C7—H7	120.6
H2A—C2—H2B	107.5	C8—C7—H7	120.6
C4—C3—C8	117.9 (2)	C7—C8—C3	121.6 (2)
C4—C3—C2	120.9 (2)	C7—C8—H8	119.2
C8—C3—C2	121.2 (2)	C3—C8—H8	119.2
C5—C4—C3	121.3 (2)	C1—N1—H11	120.9 (16)
C5—C4—H4	119.3	C1—N1—H12	121.7 (18)
C3—C4—H4	119.3	H11—N1—H12	117 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1i	0.88 (1)	2.05 (1)	2.911 (2)	165 (2)
N1—H12···O1ii	0.89 (1)	2.22 (1)	3.064 (3)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O1i	0.88 (1)	2.05 (1)	2.911 (2)	165 (2)
N1—H12⋯O1ii	0.89 (1)	2.22 (1)	3.064 (3)	157 (2)

Symmetry codes: (i) ; (ii) .