2-Chloro-N-(3,4-dimethyl-phen-yl)acetamide.

The conformation of the C=O bond in the structure of the title compound, C(10)H(12)ClNO, is anti to the N-H bond and to the methyl-ene H atoms in the side chain in both the independent mol-ecules comprising the asymmetric unit. However, the conformation of the N-H bond is syn to the meta-methyl substituent in the aromatic ring of one of the mol-ecules and anti in the other mol-ecule. The two independent mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonding into chains parallel to the b axis.

Related literature

For preparation of the compound, see: Shilpa & Gowda (2007 ▶). For related structures, see: Gowda et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C10H12ClNO

M = 197.66

Triclinic,

a = 8.3672 (9) Å

b = 9.8076 (9) Å

c = 12.409 (1) Å

α = 95.415 (8)°

β = 96.492 (9)°

γ = 97.767 (9)°

V = 996.26 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 299 K

0.44 × 0.36 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.868, T max = 0.936

10754 measured reflections

3634 independent reflections

2874 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.127

S = 0.97

3634 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013051/dn2441sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013051/dn2441Isup2.hkl

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

C10H12ClNO	Z = 4
Mr = 197.66	F(000) = 416
Triclinic, P1	Dx = 1.318 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3672 (9) Å	Cell parameters from 4345 reflections
b = 9.8076 (9) Å	θ = 2.8–27.6°
c = 12.409 (1) Å	µ = 0.34 mm−1
α = 95.415 (8)°	T = 299 K
β = 96.492 (9)°	Rod, colourless
γ = 97.767 (9)°	0.44 × 0.36 × 0.20 mm
V = 996.26 (16) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3634 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −10→10
Tmin = 0.868, Tmax = 0.936	k = −11→11
10754 measured reflections	l = −14→14

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
3634 reflections	Δρmax = 0.19 e Å−3
240 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

Experimental. Absorption correction: empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlis RED (Oxford Diffraction, 2007).

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	0.62739 (6)	0.60024 (5)	0.62240 (4)	0.0701 (2)
O1	0.83974 (16)	0.76355 (11)	0.45971 (10)	0.0569 (3)
N1	0.81699 (17)	0.54085 (13)	0.38380 (11)	0.0477 (3)
H1N	0.8113	0.4570	0.3998	0.057*
C1	0.81633 (19)	0.55916 (15)	0.27115 (14)	0.0447 (4)
C2	0.9174 (2)	0.66380 (16)	0.23435 (14)	0.0482 (4)
H2	0.9875	0.7272	0.2846	0.058*
C3	0.9155 (2)	0.67553 (17)	0.12342 (14)	0.0490 (4)
C4	0.8120 (2)	0.57967 (18)	0.04769 (14)	0.0542 (4)
C5	0.7129 (2)	0.47505 (18)	0.08636 (16)	0.0627 (5)
H5	0.6434	0.4105	0.0367	0.075*
C6	0.7148 (2)	0.46423 (17)	0.19551 (16)	0.0575 (5)
H6	0.6474	0.3926	0.2190	0.069*
C7	0.82545 (19)	0.63949 (16)	0.46785 (14)	0.0446 (4)
C8	0.8184 (2)	0.58415 (19)	0.57750 (14)	0.0546 (4)
H8A	0.9049	0.6356	0.6304	0.066*
H8B	0.8339	0.4876	0.5710	0.066*
C9	1.0278 (3)	0.7913 (2)	0.08682 (19)	0.0753 (6)
H9A	1.0907	0.8458	0.1495	0.090*
H9B	0.9646	0.8488	0.0466	0.090*
H9C	1.0995	0.7528	0.0411	0.090*
C10	0.8062 (3)	0.5877 (3)	−0.07390 (16)	0.0781 (6)
H10A	0.9126	0.5838	−0.0949	0.094*
H10B	0.7710	0.6731	−0.0913	0.094*
H10C	0.7314	0.5112	−0.1126	0.094*
Cl2	0.90424 (8)	0.14166 (5)	0.21372 (4)	0.0779 (2)
O2	0.78329 (17)	0.24929 (11)	0.41405 (11)	0.0628 (4)
N2	0.74319 (15)	0.04521 (12)	0.48565 (10)	0.0414 (3)
H2N	0.7539	−0.0406	0.4734	0.050*
C11	0.67313 (18)	0.08227 (14)	0.58097 (12)	0.0379 (3)
C12	0.66625 (19)	−0.01217 (15)	0.65716 (12)	0.0428 (4)
H12	0.7076	−0.0946	0.6435	0.051*
C13	0.5996 (2)	0.01258 (16)	0.75308 (13)	0.0458 (4)
C14	0.53726 (19)	0.13642 (16)	0.77369 (13)	0.0459 (4)
C15	0.5432 (2)	0.22884 (16)	0.69622 (14)	0.0503 (4)
H15	0.5011	0.3110	0.7092	0.060*
C16	0.60886 (19)	0.20418 (15)	0.60076 (14)	0.0466 (4)
H16	0.6102	0.2683	0.5501	0.056*
C17	0.79504 (19)	0.12730 (15)	0.41182 (13)	0.0425 (4)
C18	0.8760 (2)	0.05019 (18)	0.32656 (13)	0.0519 (4)
H18A	0.8097	−0.0386	0.3018	0.062*
H18B	0.9808	0.0326	0.3598	0.062*
C19	0.5979 (3)	−0.0922 (2)	0.83395 (16)	0.0698 (6)
H19A	0.6609	−0.0513	0.9016	0.084*
H19B	0.6439	−0.1707	0.8058	0.084*
H19C	0.4879	−0.1216	0.8462	0.084*
C20	0.4663 (2)	0.1688 (2)	0.87824 (15)	0.0639 (5)
H20A	0.5468	0.1673	0.9396	0.077*
H20B	0.3736	0.1008	0.8819	0.077*
H20C	0.4333	0.2589	0.8797	0.077*

	U11	U22	U33	U12	U13	U23
Cl1	0.0802 (4)	0.0660 (3)	0.0721 (3)	0.0167 (3)	0.0302 (3)	0.0161 (2)
O1	0.0811 (9)	0.0320 (6)	0.0606 (7)	0.0144 (5)	0.0136 (6)	0.0069 (5)
N1	0.0598 (9)	0.0290 (6)	0.0568 (8)	0.0085 (6)	0.0128 (7)	0.0085 (6)
C1	0.0469 (9)	0.0323 (7)	0.0568 (9)	0.0115 (7)	0.0090 (7)	0.0041 (7)
C2	0.0470 (9)	0.0380 (8)	0.0578 (10)	0.0046 (7)	0.0043 (8)	0.0017 (7)
C3	0.0500 (10)	0.0447 (9)	0.0559 (10)	0.0142 (7)	0.0101 (8)	0.0097 (7)
C4	0.0570 (10)	0.0513 (10)	0.0570 (10)	0.0243 (8)	0.0029 (8)	0.0020 (8)
C5	0.0653 (12)	0.0478 (10)	0.0682 (12)	0.0054 (9)	−0.0037 (10)	−0.0101 (8)
C6	0.0618 (11)	0.0374 (8)	0.0703 (12)	0.0011 (8)	0.0095 (9)	−0.0023 (8)
C7	0.0437 (9)	0.0356 (8)	0.0567 (9)	0.0099 (7)	0.0073 (7)	0.0093 (7)
C8	0.0596 (11)	0.0477 (9)	0.0584 (10)	0.0104 (8)	0.0066 (8)	0.0126 (8)
C9	0.0797 (14)	0.0735 (14)	0.0735 (13)	−0.0002 (11)	0.0189 (11)	0.0176 (11)
C10	0.0970 (17)	0.0832 (15)	0.0568 (12)	0.0346 (13)	−0.0021 (11)	0.0040 (10)
Cl2	0.1111 (5)	0.0687 (3)	0.0604 (3)	0.0094 (3)	0.0316 (3)	0.0223 (2)
O2	0.0880 (10)	0.0318 (6)	0.0763 (8)	0.0136 (6)	0.0275 (7)	0.0190 (6)
N2	0.0518 (8)	0.0259 (6)	0.0483 (7)	0.0061 (5)	0.0106 (6)	0.0073 (5)
C11	0.0379 (8)	0.0299 (7)	0.0447 (8)	0.0025 (6)	0.0036 (6)	0.0037 (6)
C12	0.0499 (9)	0.0299 (7)	0.0508 (9)	0.0097 (6)	0.0084 (7)	0.0073 (6)
C13	0.0516 (9)	0.0404 (8)	0.0446 (8)	0.0056 (7)	0.0048 (7)	0.0046 (7)
C14	0.0440 (9)	0.0428 (8)	0.0485 (9)	0.0040 (7)	0.0046 (7)	−0.0027 (7)
C15	0.0528 (10)	0.0358 (8)	0.0636 (10)	0.0134 (7)	0.0093 (8)	0.0003 (7)
C16	0.0519 (9)	0.0322 (7)	0.0581 (10)	0.0102 (7)	0.0080 (8)	0.0101 (7)
C17	0.0458 (9)	0.0334 (8)	0.0480 (9)	0.0021 (6)	0.0059 (7)	0.0091 (6)
C18	0.0618 (11)	0.0465 (9)	0.0510 (9)	0.0088 (8)	0.0151 (8)	0.0134 (7)
C19	0.0980 (16)	0.0619 (11)	0.0592 (11)	0.0223 (11)	0.0262 (11)	0.0215 (9)
C20	0.0684 (12)	0.0652 (12)	0.0567 (11)	0.0089 (10)	0.0157 (9)	−0.0078 (9)

Cl1—C8	1.7731 (19)	Cl2—C18	1.7539 (16)
O1—C7	1.2213 (18)	O2—C17	1.2117 (18)
N1—C7	1.343 (2)	N2—C17	1.3454 (19)
N1—C1	1.426 (2)	N2—C11	1.4171 (19)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.382 (2)	C11—C12	1.385 (2)
C1—C2	1.385 (2)	C11—C16	1.388 (2)
C2—C3	1.391 (2)	C12—C13	1.385 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.395 (2)	C13—C14	1.398 (2)
C3—C9	1.511 (3)	C13—C19	1.503 (2)
C4—C5	1.387 (3)	C14—C15	1.383 (2)
C4—C10	1.514 (3)	C14—C20	1.511 (2)
C5—C6	1.367 (3)	C15—C16	1.376 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.516 (2)	C17—C18	1.517 (2)
C8—H8A	0.9700	C18—H18A	0.9700
C8—H8B	0.9700	C18—H18B	0.9700
C9—H9A	0.9600	C19—H19A	0.9600
C9—H9B	0.9600	C19—H19B	0.9600
C9—H9C	0.9600	C19—H19C	0.9600
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600
C7—N1—C1	127.45 (13)	C17—N2—C11	128.24 (12)
C7—N1—H1N	116.3	C17—N2—H2N	115.9
C1—N1—H1N	116.3	C11—N2—H2N	115.9
C6—C1—C2	118.88 (16)	C12—C11—C16	118.87 (14)
C6—C1—N1	118.09 (15)	C12—C11—N2	116.84 (13)
C2—C1—N1	122.98 (14)	C16—C11—N2	124.27 (13)
C1—C2—C3	120.99 (15)	C11—C12—C13	121.92 (14)
C1—C2—H2	119.5	C11—C12—H12	119.0
C3—C2—H2	119.5	C13—C12—H12	119.0
C2—C3—C4	119.72 (16)	C12—C13—C14	119.13 (15)
C2—C3—C9	119.26 (16)	C12—C13—C19	119.77 (15)
C4—C3—C9	121.02 (17)	C14—C13—C19	121.09 (16)
C5—C4—C3	118.29 (16)	C15—C14—C13	118.25 (15)
C5—C4—C10	120.04 (17)	C15—C14—C20	120.87 (16)
C3—C4—C10	121.68 (18)	C13—C14—C20	120.88 (16)
C6—C5—C4	121.78 (16)	C16—C15—C14	122.68 (15)
C6—C5—H5	119.1	C16—C15—H15	118.7
C4—C5—H5	119.1	C14—C15—H15	118.7
C5—C6—C1	120.34 (17)	C15—C16—C11	119.14 (14)
C5—C6—H6	119.8	C15—C16—H16	120.4
C1—C6—H6	119.8	C11—C16—H16	120.4
O1—C7—N1	124.51 (15)	O2—C17—N2	124.59 (15)
O1—C7—C8	121.48 (15)	O2—C17—C18	123.45 (14)
N1—C7—C8	114.00 (14)	N2—C17—C18	111.93 (13)
C7—C8—Cl1	109.74 (12)	C17—C18—Cl2	112.79 (12)
C7—C8—H8A	109.7	C17—C18—H18A	109.0
Cl1—C8—H8A	109.7	Cl2—C18—H18A	109.0
C7—C8—H8B	109.7	C17—C18—H18B	109.0
Cl1—C8—H8B	109.7	Cl2—C18—H18B	109.0
H8A—C8—H8B	108.2	H18A—C18—H18B	107.8
C3—C9—H9A	109.5	C13—C19—H19A	109.5
C3—C9—H9B	109.5	C13—C19—H19B	109.5
H9A—C9—H9B	109.5	H19A—C19—H19B	109.5
C3—C9—H9C	109.5	C13—C19—H19C	109.5
H9A—C9—H9C	109.5	H19A—C19—H19C	109.5
H9B—C9—H9C	109.5	H19B—C19—H19C	109.5
C4—C10—H10A	109.5	C14—C20—H20A	109.5
C4—C10—H10B	109.5	C14—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C4—C10—H10C	109.5	C14—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5
C7—N1—C1—C6	−140.52 (16)	C17—N2—C11—C12	−164.70 (14)
C7—N1—C1—C2	42.3 (2)	C17—N2—C11—C16	16.8 (2)
C6—C1—C2—C3	1.1 (2)	C16—C11—C12—C13	−1.1 (2)
N1—C1—C2—C3	178.30 (14)	N2—C11—C12—C13	−179.64 (14)
C1—C2—C3—C4	−0.8 (2)	C11—C12—C13—C14	0.1 (2)
C1—C2—C3—C9	180.00 (16)	C11—C12—C13—C19	−178.89 (16)
C2—C3—C4—C5	0.2 (2)	C12—C13—C14—C15	0.7 (2)
C9—C3—C4—C5	179.41 (17)	C19—C13—C14—C15	179.67 (16)
C2—C3—C4—C10	−179.69 (17)	C12—C13—C14—C20	−178.87 (15)
C9—C3—C4—C10	−0.5 (3)	C19—C13—C14—C20	0.1 (3)
C3—C4—C5—C6	0.0 (3)	C13—C14—C15—C16	−0.5 (3)
C10—C4—C5—C6	179.91 (18)	C20—C14—C15—C16	179.05 (16)
C4—C5—C6—C1	0.4 (3)	C14—C15—C16—C11	−0.5 (3)
C2—C1—C6—C5	−0.9 (3)	C12—C11—C16—C15	1.2 (2)
N1—C1—C6—C5	−178.21 (16)	N2—C11—C16—C15	179.71 (14)
C1—N1—C7—O1	−2.7 (3)	C11—N2—C17—O2	−3.0 (3)
C1—N1—C7—C8	178.29 (15)	C11—N2—C17—C18	175.03 (14)
O1—C7—C8—Cl1	73.33 (19)	O2—C17—C18—Cl2	−15.1 (2)
N1—C7—C8—Cl1	−107.59 (15)	N2—C17—C18—Cl2	166.82 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.05	2.8992 (16)	172
N2—H2N···O1i	0.86	2.14	2.9802 (16)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86	2.05	2.8992 (16)	172
N2—H2N⋯O1i	0.86	2.14	2.9802 (16)	166

Symmetry code: (i) .