N-(3-Chloro-phen-yl)acetamide.

The conformation of the N-H bond in the structure of the title compound (3CPA), C(8)H(8)ClNO, is anti to the meta-chloro substituent, in contrast to the syn conformation observed for the ortho-chloro substituent in N-(2-chloro-phen-yl)acetamide, syn to both the ortho and meta chloro substituents in N-(2,3-dichloro-phen-yl)acetamide, and syn to the ortho chloro substituent in N-(2,4-dichloro-phen-yl)acetamide. There are two mol-ecules, linked by an N-H⋯O hydrogen bond, in the asymmetric unit of 3CPA. The bond parameters in 3CPA are similar to those of other acetanilides and the mol-ecules are packed into chains through inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2006 ▶); Gowda, Foro & Fuess (2007 ▶); Gowda, Svoboda & Fuess (2007 ▶); Pies et al. (1971 ▶).

Experimental

Crystal data

C8H8ClNO

M = 169.60

Orthorhombic,

a = 4.8468 (8) Å

b = 18.562 (2) Å

c = 18.852 (3) Å

V = 1696.0 (4) Å3

Z = 8

Cu Kα radiation

μ = 3.51 mm−1

T = 299 (2) K

0.60 × 0.15 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.225, T max = 0.756

3119 measured reflections

2780 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.019

3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.224

S = 1.07

2780 reflections

207 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.59 e Å−3

Absolute structure: Flack (1983 ▶), 987 Friedel pairs

Flack parameter: 0.00 (4)

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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068808/dn2306sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068808/dn2306Isup2.hkl

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

C8H8ClNO	F000 = 704
Mr = 169.60	Dx = 1.328 Mg m−3
Orthorhombic, P212121	Cu Kα radiation λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 4.8468 (8) Å	θ = 4.8–19.8º
b = 18.562 (2) Å	µ = 3.51 mm−1
c = 18.852 (3) Å	T = 299 (2) K
V = 1696.0 (4) Å3	Needle, colourless
Z = 8	0.60 × 0.15 × 0.08 mm

Enraf–Nonius CAD4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 67.0º
Monochromator: graphite	θmin = 3.3º
T = 299(2) K	h = −5→0
ω/2θ scans	k = −22→0
Absorption correction: ψ scan(North et al., 1968)	l = −22→14
Tmin = 0.225, Tmax = 0.757	3 standard reflections
3119 measured reflections	every 120 min
2780 independent reflections	intensity decay: 2.0%
2098 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.082	w = 1/[σ2(Fo2) + (0.1656P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.224	(Δ/σ)max = 0.002
S = 1.07	Δρmax = 0.43 e Å−3
2780 reflections	Δρmin = −0.59 e Å−3
207 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 987 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (4)
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	0.3831 (6)	0.37160 (11)	0.39860 (11)	0.1367 (10)
O1	−0.0630 (10)	0.23187 (18)	0.2036 (2)	0.0880 (12)
N1	0.0399 (8)	0.14104 (19)	0.2789 (2)	0.0641 (10)
H1N	0.028 (12)	0.0957 (12)	0.288 (3)	0.077*
C1	0.2186 (9)	0.1757 (2)	0.3267 (3)	0.0609 (11)
C2	0.2211 (11)	0.2491 (3)	0.3358 (3)	0.0687 (13)
H2	0.1068	0.2782	0.3084	0.082*
C3	0.3931 (14)	0.2792 (4)	0.3853 (3)	0.0854 (17)
C4	0.5720 (14)	0.2367 (6)	0.4257 (4)	0.108 (3)
H4	0.6915	0.2575	0.4584	0.130*
C5	0.5665 (16)	0.1649 (6)	0.4158 (4)	0.116 (3)
H5	0.6851	0.1359	0.4421	0.139*
C6	0.3871 (13)	0.1324 (4)	0.3669 (3)	0.0868 (16)
H6	0.3823	0.0825	0.3619	0.104*
C7	−0.0907 (10)	0.1695 (2)	0.2219 (3)	0.0608 (11)
C8	−0.2696 (12)	0.1186 (3)	0.1825 (3)	0.0804 (15)
H8A	−0.2326	0.0703	0.1980	0.121*
H8B	−0.2325	0.1225	0.1326	0.121*
H8C	−0.4597	0.1301	0.1913	0.121*
Cl2	0.6744 (5)	0.49383 (10)	−0.03716 (11)	0.1181 (8)
O2	0.0909 (9)	0.49682 (17)	0.1824 (2)	0.0865 (12)
N2	0.1055 (8)	0.37741 (16)	0.1625 (2)	0.0552 (9)
H2N	0.085 (12)	0.3348 (13)	0.175 (3)	0.066*
C9	0.3111 (8)	0.3741 (2)	0.1092 (2)	0.0493 (9)
C10	0.3766 (11)	0.4316 (2)	0.0668 (3)	0.0635 (12)
H10	0.2864	0.4756	0.0715	0.076*
C11	0.5868 (12)	0.4215 (3)	0.0158 (3)	0.0679 (13)
C12	0.7118 (10)	0.3568 (3)	0.0071 (3)	0.0675 (12)
H12	0.8437	0.3510	−0.0283	0.081*
C13	0.6462 (10)	0.3011 (3)	0.0493 (3)	0.0673 (13)
H13	0.7374	0.2573	0.0441	0.081*
C14	0.4402 (9)	0.3086 (2)	0.1013 (3)	0.0587 (11)
H14	0.3920	0.2698	0.1300	0.070*
C15	0.0080 (9)	0.4367 (2)	0.1948 (3)	0.0593 (11)
C16	−0.2118 (12)	0.4235 (3)	0.2501 (3)	0.0800 (15)
H16A	−0.2754	0.3746	0.2467	0.120*
H16B	−0.3636	0.4558	0.2423	0.120*
H16C	−0.1362	0.4317	0.2964	0.120*

	U11	U22	U33	U12	U13	U23
Cl1	0.172 (2)	0.1231 (14)	0.1148 (14)	−0.0737 (15)	0.0260 (16)	−0.0395 (11)
O1	0.094 (3)	0.0659 (19)	0.104 (3)	−0.0177 (19)	−0.023 (2)	0.0274 (19)
N1	0.057 (2)	0.0524 (18)	0.082 (3)	−0.0095 (16)	−0.003 (2)	0.0140 (19)
C1	0.041 (2)	0.075 (3)	0.067 (3)	−0.0049 (19)	0.003 (2)	0.008 (2)
C2	0.058 (3)	0.078 (3)	0.070 (3)	−0.014 (2)	0.005 (3)	0.003 (2)
C3	0.068 (4)	0.115 (4)	0.073 (3)	−0.034 (3)	0.023 (3)	−0.011 (3)
C4	0.053 (3)	0.188 (8)	0.083 (4)	−0.032 (4)	−0.001 (3)	−0.026 (5)
C5	0.075 (4)	0.176 (8)	0.097 (5)	0.034 (5)	−0.025 (4)	−0.007 (5)
C6	0.070 (3)	0.104 (4)	0.086 (4)	0.020 (3)	−0.010 (3)	0.007 (3)
C7	0.054 (2)	0.055 (2)	0.073 (3)	−0.0023 (19)	−0.003 (2)	0.009 (2)
C8	0.062 (3)	0.085 (3)	0.093 (4)	−0.013 (3)	−0.010 (3)	0.001 (3)
Cl2	0.1326 (17)	0.1002 (11)	0.1217 (13)	−0.0127 (11)	0.0357 (13)	0.0404 (10)
O2	0.086 (3)	0.0506 (16)	0.123 (3)	0.0048 (19)	0.018 (2)	−0.0152 (18)
N2	0.0491 (18)	0.0411 (15)	0.075 (2)	−0.0052 (15)	0.0041 (19)	−0.0026 (16)
C9	0.0391 (18)	0.0504 (19)	0.058 (2)	−0.0029 (15)	−0.0012 (19)	−0.0094 (18)
C10	0.058 (3)	0.051 (2)	0.081 (3)	0.005 (2)	0.004 (2)	0.006 (2)
C11	0.067 (3)	0.071 (3)	0.066 (3)	−0.016 (2)	0.001 (3)	0.007 (2)
C12	0.047 (2)	0.081 (3)	0.075 (3)	−0.002 (2)	0.007 (2)	−0.007 (3)
C13	0.040 (2)	0.072 (3)	0.090 (3)	0.009 (2)	0.008 (2)	−0.009 (2)
C14	0.051 (2)	0.050 (2)	0.075 (3)	−0.0008 (18)	−0.003 (2)	0.001 (2)
C15	0.052 (2)	0.053 (2)	0.073 (3)	0.0010 (18)	0.000 (2)	−0.007 (2)
C16	0.054 (3)	0.089 (3)	0.097 (4)	0.004 (2)	0.012 (3)	−0.015 (3)

Cl1—C3	1.735 (7)	Cl2—C11	1.726 (5)
O1—C7	1.215 (5)	O2—C15	1.209 (6)
N1—C7	1.355 (6)	N2—C15	1.343 (5)
N1—C1	1.406 (6)	N2—C9	1.416 (5)
N1—H1N	0.86 (2)	N2—H2N	0.830 (19)
C1—C2	1.373 (7)	C9—C10	1.371 (6)
C1—C6	1.375 (7)	C9—C14	1.376 (6)
C2—C3	1.371 (8)	C10—C11	1.414 (8)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.397 (11)	C11—C12	1.354 (7)
C4—C5	1.347 (12)	C12—C13	1.343 (7)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.403 (10)	C13—C14	1.407 (7)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.482 (7)	C15—C16	1.511 (7)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C7—N1—C1	128.1 (4)	C15—N2—C9	127.2 (4)
C7—N1—H1N	121 (4)	C15—N2—H2N	128 (4)
C1—N1—H1N	111 (4)	C9—N2—H2N	104 (4)
C2—C1—C6	120.5 (5)	C10—C9—C14	121.3 (4)
C2—C1—N1	122.6 (4)	C10—C9—N2	122.9 (4)
C6—C1—N1	116.8 (5)	C14—C9—N2	115.8 (4)
C3—C2—C1	119.6 (6)	C9—C10—C11	117.4 (4)
C3—C2—H2	120.2	C9—C10—H10	121.3
C1—C2—H2	120.2	C11—C10—H10	121.3
C2—C3—C4	121.3 (7)	C12—C11—C10	121.5 (4)
C2—C3—Cl1	118.9 (6)	C12—C11—Cl2	120.6 (4)
C4—C3—Cl1	119.8 (6)	C10—C11—Cl2	117.8 (4)
C5—C4—C3	118.1 (6)	C13—C12—C11	120.3 (5)
C5—C4—H4	121.0	C13—C12—H12	119.8
C3—C4—H4	121.0	C11—C12—H12	119.8
C4—C5—C6	121.9 (7)	C12—C13—C14	120.4 (4)
C4—C5—H5	119.0	C12—C13—H13	119.8
C6—C5—H5	119.0	C14—C13—H13	119.8
C1—C6—C5	118.6 (6)	C9—C14—C13	119.0 (4)
C1—C6—H6	120.7	C9—C14—H14	120.5
C5—C6—H6	120.7	C13—C14—H14	120.5
O1—C7—N1	123.0 (5)	O2—C15—N2	123.5 (5)
O1—C7—C8	122.0 (5)	O2—C15—C16	121.1 (4)
N1—C7—C8	114.9 (4)	N2—C15—C16	115.4 (4)
C7—C8—H8A	109.5	C15—C16—H16A	109.5
C7—C8—H8B	109.5	C15—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C7—C8—H8C	109.5	C15—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
C7—N1—C1—C2	21.1 (8)	C15—N2—C9—C10	−22.1 (7)
C7—N1—C1—C6	−161.3 (5)	C15—N2—C9—C14	159.1 (5)
C6—C1—C2—C3	0.0 (8)	C14—C9—C10—C11	−1.5 (7)
N1—C1—C2—C3	177.5 (5)	N2—C9—C10—C11	179.8 (4)
C1—C2—C3—C4	1.8 (8)	C9—C10—C11—C12	2.4 (8)
C1—C2—C3—Cl1	−177.4 (4)	C9—C10—C11—Cl2	−179.1 (4)
C2—C3—C4—C5	−1.6 (10)	C10—C11—C12—C13	−2.8 (8)
Cl1—C3—C4—C5	177.5 (6)	Cl2—C11—C12—C13	178.8 (4)
C3—C4—C5—C6	−0.3 (12)	C11—C12—C13—C14	2.2 (8)
C2—C1—C6—C5	−1.8 (9)	C10—C9—C14—C13	0.9 (7)
N1—C1—C6—C5	−179.4 (6)	N2—C9—C14—C13	179.8 (4)
C4—C5—C6—C1	2.0 (11)	C12—C13—C14—C9	−1.3 (7)
C1—N1—C7—O1	1.5 (8)	C9—N2—C15—O2	−1.2 (8)
C1—N1—C7—C8	−179.1 (5)	C9—N2—C15—C16	−179.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (2)	2.00 (2)	2.846 (5)	166 (6)
N2—H2N···O1	0.830 (19)	2.11 (2)	2.927 (5)	167 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (2)	2.00 (2)	2.846 (5)	166 (6)
N2—H2N⋯O1	0.830 (19)	2.11 (2)	2.927 (5)	167 (6)

Symmetry code: (i) .