2,2,2-Trichloro-N-(2,5-dimethyl-phen-yl)acetamide.

The N-H bond in the title compound, C(10)H(10)Cl(3)NO, is syn to the 2-methyl and anti to the 5-methyl substituent of the aromatic ring. Adjacent mol-ecules are linked into chains through N-H⋯O hydrogen bonding. Two Cl atoms are each disordered equally over two sites.

Related literature

For related literature, see: Gowda, Foro & Fuess (2007 ▶); Gowda, Kožíšek et al. (2007 ▶); Shilpa & Gowda (2007 ▶).

Experimental

Crystal data

C10H10Cl3NO

M = 266.54

Orthorhombic,

a = 4.9173 (9) Å

b = 11.290 (1) Å

c = 21.070 (2) Å

V = 1169.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 299 (2) K

0.16 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.889, T max = 0.956

6121 measured reflections

2314 independent reflections

703 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.308

S = 0.86

2314 reflections

154 parameters

37 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.76 e Å−3

Absolute structure: Flack (1983 ▶), 887 Friedel pairs

Flack parameter: −0.4 (4)

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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009264/ng2441sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009264/ng2441Isup2.hkl

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

C10H10Cl3NO	F000 = 544
Mr = 266.54	Dx = 1.514 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1061 reflections
a = 4.9173 (9) Å	θ = 2.6–28.1º
b = 11.290 (1) Å	µ = 0.76 mm−1
c = 21.070 (2) Å	T = 299 (2) K
V = 1169.7 (3) Å3	Prism, colourless
Z = 4	0.16 × 0.12 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2314 independent reflections
Radiation source: Enhance (Mo) X-ray Source	703 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.071
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and phi scans.	θmin = 3.4º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −6→6
Tmin = 0.889, Tmax = 0.956	k = −14→13
6121 measured reflections	l = −26→23

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.088	w = 1/[σ2(Fo2) + (0.1675P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.309	(Δ/σ)max = 0.003
S = 0.86	Δρmax = 0.27 e Å−3
2314 reflections	Δρmin = −0.76 e Å−3
154 parameters	Extinction correction: none
37 restraints	Absolute structure: Flack (1983), 887 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.4 (4)
Secondary atom site location: difference Fourier map

Experimental. empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm

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	Occ. (<1)
Cl1A	0.4909 (19)	0.3895 (7)	0.5055 (3)	0.096 (2)	0.50
Cl1B	0.301 (3)	0.3888 (10)	0.5125 (4)	0.139 (4)	0.50
Cl2	0.0276 (14)	0.5253 (7)	0.5201 (3)	0.218 (3)
Cl3A	0.459 (2)	0.6280 (6)	0.4526 (3)	0.102 (2)	0.50
Cl3B	0.226 (2)	0.6324 (7)	0.4737 (5)	0.141 (3)	0.50
O6	−0.0518 (17)	0.4448 (7)	0.3920 (4)	0.092 (3)
N7	0.3670 (16)	0.4054 (7)	0.3571 (4)	0.069 (2)
H7N	0.5356	0.4163	0.3662	0.083*
C4	0.311 (2)	0.4931 (7)	0.4592 (4)	0.082 (3)
C5	0.180 (3)	0.4444 (9)	0.4003 (6)	0.075 (3)
C8	0.308 (2)	0.3488 (8)	0.2991 (4)	0.055 (3)
C9	0.4334 (19)	0.2416 (9)	0.2866 (5)	0.062 (3)
C10	0.358 (2)	0.1877 (10)	0.2267 (5)	0.079 (3)
H10	0.4336	0.1151	0.2154	0.095*
C11	0.178 (2)	0.2420 (10)	0.1863 (4)	0.067 (3)
H11	0.1371	0.2054	0.1480	0.080*
C12	0.055 (2)	0.3486 (10)	0.2002 (5)	0.069 (3)
C13	0.125 (2)	0.4011 (9)	0.2572 (4)	0.062 (3)
H13	0.0466	0.4735	0.2679	0.074*
C14	0.624 (2)	0.1827 (8)	0.3309 (5)	0.075 (3)
H14A	0.5312	0.1655	0.3700	0.090*
H14B	0.7750	0.2341	0.3392	0.090*
H14C	0.6878	0.1103	0.3123	0.090*
C15	−0.138 (2)	0.4037 (11)	0.1548 (5)	0.091 (3)
H15A	−0.2838	0.3497	0.1462	0.109*
H15B	−0.0441	0.4218	0.1160	0.109*
H15C	−0.2094	0.4753	0.1727	0.109*

	U11	U22	U33	U12	U13	U23
Cl1A	0.116 (6)	0.109 (5)	0.063 (3)	0.023 (5)	0.000 (4)	−0.003 (3)
Cl1B	0.172 (8)	0.151 (7)	0.093 (5)	−0.036 (7)	0.005 (6)	0.037 (5)
Cl2	0.213 (6)	0.278 (7)	0.163 (4)	0.011 (6)	0.007 (4)	−0.053 (4)
Cl3A	0.135 (6)	0.086 (4)	0.086 (4)	−0.038 (4)	0.016 (4)	−0.025 (3)
Cl3B	0.151 (7)	0.117 (6)	0.154 (6)	0.018 (6)	−0.027 (6)	−0.049 (5)
O6	0.052 (4)	0.127 (7)	0.099 (5)	0.011 (5)	−0.007 (4)	−0.040 (5)
N7	0.049 (5)	0.068 (5)	0.092 (6)	−0.004 (5)	−0.014 (5)	0.016 (5)
C4	0.091 (8)	0.070 (7)	0.084 (7)	0.002 (7)	−0.025 (7)	−0.019 (6)
C5	0.056 (7)	0.081 (8)	0.088 (7)	0.011 (7)	−0.018 (7)	−0.019 (6)
C8	0.055 (6)	0.061 (6)	0.048 (5)	−0.009 (6)	0.004 (6)	−0.005 (5)
C9	0.045 (5)	0.056 (6)	0.086 (7)	0.011 (6)	0.004 (6)	0.018 (6)
C10	0.079 (8)	0.064 (7)	0.095 (8)	−0.004 (7)	0.000 (7)	−0.012 (6)
C11	0.077 (8)	0.064 (7)	0.061 (6)	−0.004 (7)	0.005 (6)	0.005 (5)
C12	0.063 (7)	0.078 (8)	0.066 (6)	−0.016 (7)	−0.003 (6)	0.022 (6)
C13	0.062 (6)	0.062 (5)	0.062 (6)	0.006 (6)	−0.005 (6)	0.010 (5)
C14	0.073 (7)	0.050 (6)	0.102 (7)	0.001 (7)	−0.004 (7)	0.000 (6)
C15	0.080 (8)	0.119 (9)	0.074 (6)	−0.001 (9)	−0.017 (7)	0.019 (7)

Cl1A—C4	1.761 (11)	C10—C11	1.373 (14)
Cl1B—C4	1.628 (11)	C10—H10	0.9300
Cl2—C4	1.931 (10)	C11—C12	1.378 (13)
Cl3A—C4	1.693 (10)	C11—H11	0.9300
Cl3B—C4	1.656 (10)	C12—C13	1.382 (14)
O6—C5	1.151 (11)	C12—C15	1.484 (14)
N7—C5	1.367 (13)	C13—H13	0.9300
N7—C8	1.411 (11)	C14—H14A	0.9600
N7—H7N	0.8600	C14—H14B	0.9600
C4—C5	1.503 (13)	C14—H14C	0.9600
C8—C9	1.383 (12)	C15—H15A	0.9600
C8—C13	1.393 (13)	C15—H15B	0.9600
C9—C10	1.449 (14)	C15—H15C	0.9600
C9—C14	1.480 (12)
C5—N7—C8	125.7 (8)	C10—C9—C14	121.5 (9)
C5—N7—H7N	117.1	C11—C10—C9	121.1 (10)
C8—N7—H7N	117.1	C11—C10—H10	119.5
C5—C4—Cl1B	106.9 (8)	C9—C10—H10	119.5
C5—C4—Cl3B	113.0 (8)	C10—C11—C12	122.8 (10)
Cl1B—C4—Cl3B	123.5 (8)	C10—C11—H11	118.6
C5—C4—Cl3A	116.5 (7)	C12—C11—H11	118.6
Cl1B—C4—Cl3A	136.1 (7)	C11—C12—C13	116.8 (9)
Cl3B—C4—Cl3A	43.0 (5)	C11—C12—C15	120.6 (10)
C5—C4—Cl1A	115.4 (7)	C13—C12—C15	122.6 (11)
Cl1B—C4—Cl1A	32.1 (4)	C12—C13—C8	121.9 (9)
Cl3B—C4—Cl1A	131.0 (7)	C12—C13—H13	119.1
Cl3A—C4—Cl1A	115.4 (7)	C8—C13—H13	119.1
C5—C4—Cl2	107.8 (8)	C9—C14—H14A	109.5
Cl1B—C4—Cl2	69.8 (7)	C9—C14—H14B	109.5
Cl3B—C4—Cl2	61.1 (6)	H14A—C14—H14B	109.5
Cl3A—C4—Cl2	101.2 (5)	C9—C14—H14C	109.5
Cl1A—C4—Cl2	96.8 (6)	H14A—C14—H14C	109.5
O6—C5—N7	124.5 (10)	H14B—C14—H14C	109.5
O6—C5—C4	123.3 (12)	C12—C15—H15A	109.5
N7—C5—C4	112.1 (10)	C12—C15—H15B	109.5
C9—C8—C13	122.6 (9)	H15A—C15—H15B	109.5
C9—C8—N7	118.0 (9)	C12—C15—H15C	109.5
C13—C8—N7	119.4 (9)	H15A—C15—H15C	109.5
C8—C9—C10	114.8 (9)	H15B—C15—H15C	109.5
C8—C9—C14	123.7 (9)
C8—N7—C5—O6	−7.0 (17)	C13—C8—C9—C10	−0.2 (13)
C8—N7—C5—C4	176.0 (8)	N7—C8—C9—C10	178.7 (9)
Cl1B—C4—C5—O6	84.0 (14)	C13—C8—C9—C14	−178.4 (9)
Cl3B—C4—C5—O6	−55.0 (16)	N7—C8—C9—C14	0.6 (13)
Cl3A—C4—C5—O6	−102.5 (14)	C8—C9—C10—C11	0.6 (14)
Cl1A—C4—C5—O6	117.4 (13)	C14—C9—C10—C11	178.8 (9)
Cl2—C4—C5—O6	10.4 (14)	C9—C10—C11—C12	−1.1 (17)
Cl1B—C4—C5—N7	−99.0 (10)	C10—C11—C12—C13	1.0 (15)
Cl3B—C4—C5—N7	121.9 (10)	C10—C11—C12—C15	179.7 (10)
Cl3A—C4—C5—N7	74.5 (11)	C11—C12—C13—C8	−0.6 (14)
Cl1A—C4—C5—N7	−65.6 (11)	C15—C12—C13—C8	−179.3 (9)
Cl2—C4—C5—N7	−172.6 (7)	C9—C8—C13—C12	0.3 (14)
C5—N7—C8—C9	−127.3 (10)	N7—C8—C13—C12	−178.7 (9)
C5—N7—C8—C13	51.7 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7N···O6i	0.86	2.12	2.984 (11)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7N⋯O6i	0.86	2.12	2.984 (11)	178

Symmetry code: (i) .