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

The conformation of the N-H bond in the title compound, C(10)H(10)Cl(3)NO, is anti to the C=O bond. The amide H atom exhibits both intra-molecular N-H⋯Cl and inter-molecular N-H⋯O hydrogen bonding. The latter inter-actions link the mol-ecules into infinite chains.

Related literature

For the preparation of the title compound, see: Shilpa & Gowda (2007 ▶). For related structures, see: Gowda et al. (2007 ▶, 2008 ▶, 2009 ▶)

Experimental

Crystal data

C10H10Cl3NO

M = 266.54

Monoclinic,

a = 5.9003 (8) Å

b = 20.843 (2) Å

c = 9.996 (1) Å

β = 105.53 (1)°

V = 1184.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 299 K

0.46 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.726, T max = 0.807

9395 measured reflections

2407 independent reflections

1952 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.151

S = 1.08

2407 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.88 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/S1600536809013075/bt2926sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013075/bt2926Isup2.hkl

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

C10H10Cl3NO	F(000) = 544
Mr = 266.54	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3672 reflections
a = 5.9003 (8) Å	θ = 2.3–27.6°
b = 20.843 (2) Å	µ = 0.75 mm−1
c = 9.996 (1) Å	T = 299 K
β = 105.53 (1)°	Prism, colourless
V = 1184.4 (2) Å3	0.46 × 0.40 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2407 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
graphite	Rint = 0.015
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −7→7
Tmin = 0.726, Tmax = 0.807	k = −25→26
9395 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0592P)2 + 1.4852P] where P = (Fo2 + 2Fc2)/3
2407 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.96 e Å−3
0 restraints	Δρmin = −0.88 e Å−3

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2007) 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
Cl1	1.2122 (2)	0.19521 (5)	0.59191 (11)	0.0833 (4)
Cl2	1.1512 (2)	0.15721 (6)	0.31037 (12)	0.0939 (5)
Cl3	0.8043 (2)	0.12567 (5)	0.45005 (16)	0.0919 (4)
O1	0.8060 (5)	0.25550 (12)	0.2520 (2)	0.0643 (7)
N1	0.8025 (4)	0.28196 (11)	0.4703 (2)	0.0403 (5)
H1N	0.8600	0.2723	0.5563	0.048*
C1	0.6475 (5)	0.33590 (13)	0.4375 (3)	0.0377 (6)
C2	0.6550 (5)	0.37830 (13)	0.3319 (3)	0.0399 (6)
H2	0.7657	0.3724	0.2819	0.048*
C3	0.4996 (5)	0.42941 (13)	0.2998 (3)	0.0413 (6)
C4	0.3341 (5)	0.43886 (14)	0.3749 (3)	0.0459 (7)
C5	0.3325 (6)	0.39622 (17)	0.4814 (4)	0.0552 (8)
H5	0.2243	0.4024	0.5329	0.066*
C6	0.4852 (6)	0.34532 (15)	0.5131 (3)	0.0500 (7)
H6	0.4796	0.3174	0.5848	0.060*
C7	0.8629 (5)	0.24601 (13)	0.3758 (3)	0.0391 (6)
C8	1.0067 (5)	0.18464 (14)	0.4322 (3)	0.0440 (7)
C9	0.5074 (7)	0.47305 (17)	0.1813 (4)	0.0618 (9)
H9A	0.6361	0.4609	0.1449	0.074*
H9B	0.5285	0.5166	0.2138	0.074*
H9C	0.3625	0.4695	0.1096	0.074*
C10	0.1610 (7)	0.49358 (19)	0.3417 (4)	0.0662 (10)
H10A	0.2428	0.5334	0.3672	0.079*
H10B	0.0457	0.4884	0.3929	0.079*
H10C	0.0843	0.4937	0.2441	0.079*

	U11	U22	U33	U12	U13	U23
Cl1	0.0948 (8)	0.0602 (6)	0.0657 (6)	0.0180 (5)	−0.0288 (5)	−0.0006 (4)
Cl2	0.1151 (9)	0.1008 (9)	0.0806 (7)	0.0593 (7)	0.0517 (7)	0.0208 (6)
Cl3	0.0866 (8)	0.0481 (5)	0.1423 (11)	−0.0182 (5)	0.0329 (7)	0.0060 (6)
O1	0.0981 (18)	0.0639 (14)	0.0272 (10)	0.0322 (13)	0.0104 (11)	−0.0009 (10)
N1	0.0564 (14)	0.0378 (12)	0.0244 (10)	0.0055 (10)	0.0067 (10)	0.0019 (9)
C1	0.0476 (15)	0.0331 (13)	0.0305 (13)	−0.0007 (11)	0.0074 (11)	−0.0030 (10)
C2	0.0472 (15)	0.0398 (14)	0.0344 (14)	0.0002 (12)	0.0141 (12)	0.0006 (11)
C3	0.0482 (16)	0.0346 (14)	0.0389 (14)	−0.0022 (12)	0.0078 (12)	0.0003 (11)
C4	0.0460 (16)	0.0386 (15)	0.0520 (17)	−0.0001 (12)	0.0113 (13)	−0.0036 (13)
C5	0.0551 (19)	0.0589 (19)	0.060 (2)	0.0054 (15)	0.0295 (16)	−0.0003 (16)
C6	0.0630 (19)	0.0491 (17)	0.0430 (16)	0.0002 (15)	0.0230 (14)	0.0058 (13)
C7	0.0475 (15)	0.0370 (14)	0.0305 (13)	0.0016 (12)	0.0064 (11)	−0.0009 (11)
C8	0.0501 (17)	0.0389 (15)	0.0418 (15)	0.0020 (12)	0.0100 (13)	0.0007 (12)
C9	0.073 (2)	0.0528 (19)	0.063 (2)	0.0143 (17)	0.0238 (18)	0.0199 (16)
C10	0.059 (2)	0.057 (2)	0.084 (3)	0.0139 (17)	0.0217 (19)	0.0043 (19)

Cl1—C8	1.741 (3)	C4—C5	1.389 (5)
Cl2—C8	1.759 (3)	C4—C10	1.507 (4)
Cl3—C8	1.755 (3)	C5—C6	1.373 (5)
O1—C7	1.209 (3)	C5—H5	0.9300
N1—C7	1.327 (3)	C6—H6	0.9300
N1—C1	1.431 (3)	C7—C8	1.555 (4)
N1—H1N	0.8600	C9—H9A	0.9600
C1—C6	1.383 (4)	C9—H9B	0.9600
C1—C2	1.387 (4)	C9—H9C	0.9600
C2—C3	1.386 (4)	C10—H10A	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C4	1.395 (4)	C10—H10C	0.9600
C3—C9	1.504 (4)
C7—N1—C1	123.9 (2)	O1—C7—N1	125.6 (3)
C7—N1—H1N	118.0	O1—C7—C8	118.7 (2)
C1—N1—H1N	118.0	N1—C7—C8	115.5 (2)
C6—C1—C2	119.6 (3)	C7—C8—Cl1	114.0 (2)
C6—C1—N1	118.7 (2)	C7—C8—Cl3	107.0 (2)
C2—C1—N1	121.7 (2)	Cl1—C8—Cl3	108.74 (17)
C3—C2—C1	120.8 (3)	C7—C8—Cl2	109.6 (2)
C3—C2—H2	119.6	Cl1—C8—Cl2	109.15 (17)
C1—C2—H2	119.6	Cl3—C8—Cl2	108.17 (17)
C2—C3—C4	120.0 (3)	C3—C9—H9A	109.5
C2—C3—C9	119.3 (3)	C3—C9—H9B	109.5
C4—C3—C9	120.8 (3)	H9A—C9—H9B	109.5
C5—C4—C3	118.1 (3)	C3—C9—H9C	109.5
C5—C4—C10	120.6 (3)	H9A—C9—H9C	109.5
C3—C4—C10	121.3 (3)	H9B—C9—H9C	109.5
C6—C5—C4	122.2 (3)	C4—C10—H10A	109.5
C6—C5—H5	118.9	C4—C10—H10B	109.5
C4—C5—H5	118.9	H10A—C10—H10B	109.5
C5—C6—C1	119.4 (3)	C4—C10—H10C	109.5
C5—C6—H6	120.3	H10A—C10—H10C	109.5
C1—C6—H6	120.3	H10B—C10—H10C	109.5
C7—N1—C1—C6	140.0 (3)	C4—C5—C6—C1	0.3 (5)
C7—N1—C1—C2	−39.4 (4)	C2—C1—C6—C5	0.6 (5)
C6—C1—C2—C3	−1.0 (4)	N1—C1—C6—C5	−178.9 (3)
N1—C1—C2—C3	178.5 (3)	C1—N1—C7—O1	3.8 (5)
C1—C2—C3—C4	0.4 (4)	C1—N1—C7—C8	−172.3 (2)
C1—C2—C3—C9	−177.9 (3)	O1—C7—C8—Cl1	145.1 (3)
C2—C3—C4—C5	0.5 (4)	N1—C7—C8—Cl1	−38.5 (3)
C9—C3—C4—C5	178.7 (3)	O1—C7—C8—Cl3	−94.6 (3)
C2—C3—C4—C10	−179.4 (3)	N1—C7—C8—Cl3	81.8 (3)
C9—C3—C4—C10	−1.1 (5)	O1—C7—C8—Cl2	22.4 (4)
C3—C4—C5—C6	−0.8 (5)	N1—C7—C8—Cl2	−161.1 (2)
C10—C4—C5—C6	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.14	2.917 (3)	149
N1—H1N···Cl1	0.86	2.57	3.003 (3)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.14	2.917 (3)	149
N1—H1N⋯Cl1	0.86	2.57	3.003 (3)	112

Symmetry code: (i) .