2-Chloro-N-(2,4-dimethyl-phen-yl)acetamide.

The conformation of the N-H bond in the structure of the title compound, C(10)H(12)ClNO, is syn to the ortho methyl group, similar to that observed with respect to the meta methyl group in 2-chloro-N-(3-methyl-phen-yl)acetamide and the ortho-chloro group in 2-chloro-N-(2-chloro-phen-yl)acetamide. The geometric parameters are similar to those of other acetanilides. The mol-ecules are linked into chains through inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2007a ▶,b ▶,c ▶,d ▶,e ▶,f ▶, 2008 ▶); Shilpa & Gowda (2007 ▶).

Experimental

Crystal data

C10H12ClNO

M = 197.66

Triclinic,

a = 4.7235 (7) Å

b = 10.407 (2) Å

c = 11.451 (2) Å

α = 67.07 (2)°

β = 86.84 (1)°

γ = 78.95 (2)°

V = 508.69 (15) Å3

Z = 2

Cu Kα radiation

μ = 3.00 mm−1

T = 299 (2) K

0.60 × 0.06 × 0.04 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.803, T max = 0.895

2059 measured reflections

1817 independent reflections

1394 reflections with I > 2σ(I)

R int = 0.015

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.190

S = 1.09

1817 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.47 e Å−3

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, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062563/bt2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062563/bt2650Isup2.hkl

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

C10H12ClNO	Z = 2
Mr = 197.66	F000 = 208
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Cu Kα radiation λ = 1.54180 Å
a = 4.7235 (7) Å	Cell parameters from 25 reflections
b = 10.407 (2) Å	θ = 4.2–26.4º
c = 11.451 (2) Å	µ = 3.00 mm−1
α = 67.07 (2)º	T = 299 (2) K
β = 86.84 (1)º	Needle, colourless
γ = 78.95 (2)º	0.60 × 0.06 × 0.04 mm
V = 508.69 (15) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.015
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 4.2º
T = 299(2) K	h = 0→5
ω/2θ scans	k = −12→12
Absorption correction: ψ scanNorth et al. (1968)	l = −13→13
Tmin = 0.803, Tmax = 0.895	3 standard reflections
2059 measured reflections	every 120 min
1817 independent reflections	intensity decay: 1.0%
1394 reflections with I > 2σ(I)

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)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.190	w = 1/[σ2(Fo2) + (0.1035P)2 + 0.2646P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.044
1817 reflections	Δρmax = 0.45 e Å−3
123 parameters	Δρmin = −0.47 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.5208 (2)	−0.02640 (14)	0.75189 (11)	0.1062 (6)
O1	0.2611 (4)	0.1946 (3)	0.5165 (2)	0.0695 (8)
N1	0.6642 (5)	0.2847 (3)	0.4451 (2)	0.0411 (6)
H1N	0.842 (8)	0.271 (3)	0.453 (3)	0.049*
C1	0.5306 (5)	0.4140 (3)	0.3481 (3)	0.0380 (6)
C2	0.6351 (5)	0.4545 (3)	0.2256 (3)	0.0426 (7)
C3	0.5019 (7)	0.5837 (3)	0.1357 (3)	0.0520 (8)
H3	0.5711	0.6130	0.0536	0.062*
C4	0.2697 (7)	0.6709 (3)	0.1634 (3)	0.0539 (8)
C5	0.1706 (7)	0.6261 (3)	0.2857 (3)	0.0536 (8)
H5	0.0142	0.6822	0.3062	0.064*
C6	0.2985 (6)	0.5003 (3)	0.3774 (3)	0.0461 (7)
H6	0.2300	0.4724	0.4597	0.055*
C7	0.5218 (5)	0.1865 (3)	0.5227 (3)	0.0449 (7)
C8	0.7104 (6)	0.0592 (4)	0.6200 (3)	0.0590 (9)
H8A	0.8681	0.0901	0.6462	0.071*
H8B	0.7927	−0.0072	0.5812	0.071*
C9	0.8830 (7)	0.3623 (4)	0.1907 (3)	0.0569 (8)
H9A	1.0565	0.3590	0.2325	0.085*
H9B	0.9069	0.4011	0.1006	0.085*
H9C	0.8435	0.2681	0.2168	0.085*
C10	0.1310 (10)	0.8109 (4)	0.0632 (4)	0.0815 (12)
H10A	0.2775	0.8560	0.0104	0.122*
H10B	0.0287	0.8712	0.1032	0.122*
H10C	−0.0013	0.7944	0.0121	0.122*

	U11	U22	U33	U12	U13	U23
Cl1	0.0551 (6)	0.1112 (9)	0.0893 (8)	−0.0082 (5)	0.0147 (5)	0.0236 (6)
O1	0.0134 (9)	0.0749 (15)	0.0926 (17)	−0.0115 (9)	−0.0051 (10)	−0.0006 (13)
N1	0.0138 (9)	0.0512 (13)	0.0519 (13)	−0.0051 (9)	−0.0010 (9)	−0.0132 (11)
C1	0.0211 (12)	0.0446 (15)	0.0476 (15)	−0.0062 (10)	−0.0031 (10)	−0.0166 (12)
C2	0.0263 (13)	0.0534 (17)	0.0504 (15)	−0.0104 (11)	0.0017 (11)	−0.0213 (13)
C3	0.0456 (17)	0.0573 (18)	0.0484 (16)	−0.0122 (14)	−0.0006 (13)	−0.0141 (14)
C4	0.0493 (18)	0.0474 (17)	0.0599 (18)	−0.0044 (13)	−0.0087 (14)	−0.0160 (14)
C5	0.0394 (16)	0.0548 (18)	0.0628 (19)	0.0047 (13)	−0.0037 (13)	−0.0242 (15)
C6	0.0278 (13)	0.0567 (17)	0.0503 (16)	−0.0021 (12)	0.0016 (11)	−0.0195 (13)
C7	0.0174 (12)	0.0522 (16)	0.0586 (17)	−0.0060 (11)	−0.0004 (11)	−0.0147 (13)
C8	0.0233 (13)	0.0593 (19)	0.073 (2)	−0.0076 (12)	−0.0009 (13)	−0.0021 (16)
C9	0.0369 (16)	0.072 (2)	0.0603 (18)	−0.0050 (14)	0.0090 (14)	−0.0270 (16)
C10	0.087 (3)	0.059 (2)	0.075 (2)	0.006 (2)	−0.009 (2)	−0.0087 (19)

Cl1—C8	1.728 (3)	C5—C6	1.371 (4)
O1—C7	1.223 (3)	C5—H5	0.9300
N1—C7	1.333 (4)	C6—H6	0.9300
N1—C1	1.425 (3)	C7—C8	1.516 (4)
N1—H1N	0.83 (4)	C8—H8A	0.9700
C1—C2	1.389 (4)	C8—H8B	0.9700
C1—C6	1.392 (4)	C9—H9A	0.9600
C2—C3	1.390 (4)	C9—H9B	0.9600
C2—C9	1.506 (4)	C9—H9C	0.9600
C3—C4	1.390 (5)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.378 (5)	C10—H10C	0.9600
C4—C10	1.511 (5)
C7—N1—C1	124.3 (2)	O1—C7—N1	123.9 (3)
C7—N1—H1N	119 (2)	O1—C7—C8	121.4 (3)
C1—N1—H1N	117 (2)	N1—C7—C8	114.6 (2)
C2—C1—C6	120.4 (3)	C7—C8—Cl1	112.3 (2)
C2—C1—N1	120.0 (2)	C7—C8—H8A	109.1
C6—C1—N1	119.6 (2)	Cl1—C8—H8A	109.1
C1—C2—C3	117.6 (3)	C7—C8—H8B	109.1
C1—C2—C9	121.6 (3)	Cl1—C8—H8B	109.1
C3—C2—C9	120.9 (3)	H8A—C8—H8B	107.9
C4—C3—C2	122.8 (3)	C2—C9—H9A	109.5
C4—C3—H3	118.6	C2—C9—H9B	109.5
C2—C3—H3	118.6	H9A—C9—H9B	109.5
C5—C4—C3	117.8 (3)	C2—C9—H9C	109.5
C5—C4—C10	120.9 (3)	H9A—C9—H9C	109.5
C3—C4—C10	121.2 (3)	H9B—C9—H9C	109.5
C6—C5—C4	121.2 (3)	C4—C10—H10A	109.5
C6—C5—H5	119.4	C4—C10—H10B	109.5
C4—C5—H5	119.4	H10A—C10—H10B	109.5
C5—C6—C1	120.3 (3)	C4—C10—H10C	109.5
C5—C6—H6	119.9	H10A—C10—H10C	109.5
C1—C6—H6	119.9	H10B—C10—H10C	109.5
C7—N1—C1—C2	−130.4 (3)	C3—C4—C5—C6	0.7 (5)
C7—N1—C1—C6	50.8 (4)	C10—C4—C5—C6	−179.0 (3)
C6—C1—C2—C3	0.7 (4)	C4—C5—C6—C1	−0.8 (5)
N1—C1—C2—C3	−178.1 (2)	C2—C1—C6—C5	0.1 (4)
C6—C1—C2—C9	−179.1 (3)	N1—C1—C6—C5	178.9 (3)
N1—C1—C2—C9	2.1 (4)	C1—N1—C7—O1	2.5 (5)
C1—C2—C3—C4	−0.9 (4)	C1—N1—C7—C8	−178.9 (3)
C9—C2—C3—C4	178.9 (3)	O1—C7—C8—Cl1	−25.2 (4)
C2—C3—C4—C5	0.2 (5)	N1—C7—C8—Cl1	156.2 (3)
C2—C3—C4—C10	179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (4)	2.04 (4)	2.853 (3)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (4)	2.04 (4)	2.853 (3)	165 (3)

Symmetry code: (i) .