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

In the title compound, C(8)H(5)Cl(3)N(2)O(3), the dihedral angle between the nitro-phenyl ring and the acetamide group is 5.47 (6)°. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains running parallel to the b axis.

Related literature

For background to acetamides, see: Khan et al. (2010 ▶); Tahir & Shad (2011 ▶). For a related structure, see: Rosli et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H5Cl3N2O3

M = 283.49

Orthorhombic,

a = 11.5164 (8) Å

b = 10.1427 (5) Å

c = 19.9054 (11) Å

V = 2325.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.78 mm−1

T = 296 K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SAINT-Plus; Bruker, 1998 ▶) T min = 0.860, T max = 0.872

8739 measured reflections

2532 independent reflections

1713 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.144

S = 1.07

2532 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶) (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036732/pv2576sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036732/pv2576Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036732/pv2576Isup3.cml

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

C8H5Cl3N2O3	F(000) = 1136
Mr = 283.49	Dx = 1.620 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2532 reflections
a = 11.5164 (8) Å	θ = 2.1–27.0°
b = 10.1427 (5) Å	µ = 0.78 mm−1
c = 19.9054 (11) Å	T = 296 K
V = 2325.1 (2) Å3	Block, yellow
Z = 8	0.20 × 0.18 × 0.18 mm

Bruker SMART APEX CCD detector diffractometer	2532 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SAINT-Plus; Bruker, 1998)	h = −5→14
Tmin = 0.860, Tmax = 0.872	k = −10→12
8739 measured reflections	l = −14→25

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.9222P] where P = (Fo2 + 2Fc2)/3
2532 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.8599 (3)	0.8973 (3)	0.29007 (15)	0.0522 (8)
C2	0.7513 (2)	0.9294 (2)	0.33324 (13)	0.0390 (6)
C3	0.5939 (2)	0.8197 (2)	0.39617 (13)	0.0367 (6)
C4	0.5685 (3)	0.7018 (3)	0.42914 (16)	0.0520 (7)
H4	0.6196	0.6310	0.4260	0.062*
C5	0.4687 (3)	0.6897 (3)	0.4662 (2)	0.0705 (10)
H5	0.4522	0.6103	0.4876	0.085*
C6	0.3927 (3)	0.7935 (3)	0.47228 (18)	0.0621 (9)
H6	0.3243	0.7852	0.4968	0.074*
C7	0.4209 (2)	0.9099 (3)	0.44096 (14)	0.0429 (6)
C8	0.5197 (2)	0.9263 (2)	0.40254 (13)	0.0387 (6)
H8A	0.5358	1.0063	0.3817	0.046*
Cl1	0.82157 (11)	0.79451 (9)	0.22201 (5)	0.0843 (4)
Cl3	0.92258 (9)	1.04369 (8)	0.25994 (5)	0.0801 (4)
Cl2	0.96357 (8)	0.81360 (10)	0.34058 (6)	0.0828 (3)
N1	0.3404 (2)	1.0223 (3)	0.44728 (15)	0.0580 (7)
N2	0.6956 (2)	0.82155 (19)	0.35614 (12)	0.0433 (6)
H2N	0.7247	0.7464	0.3454	0.052*
O1	0.72365 (18)	1.04229 (16)	0.34446 (11)	0.0524 (5)
O2	0.3623 (2)	1.1225 (2)	0.41711 (16)	0.0858 (8)
O3	0.2570 (2)	1.0101 (3)	0.48485 (16)	0.0900 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0626 (19)	0.0350 (14)	0.0589 (18)	−0.0020 (13)	0.0223 (15)	0.0010 (12)
C2	0.0444 (14)	0.0307 (12)	0.0418 (14)	−0.0010 (11)	0.0055 (13)	0.0007 (10)
C3	0.0383 (14)	0.0318 (12)	0.0400 (13)	−0.0053 (10)	−0.0002 (12)	−0.0019 (10)
C4	0.0499 (17)	0.0353 (14)	0.071 (2)	0.0007 (12)	0.0134 (16)	0.0083 (13)
C5	0.064 (2)	0.0461 (18)	0.101 (3)	−0.0008 (15)	0.027 (2)	0.0226 (17)
C6	0.0453 (17)	0.0588 (19)	0.082 (2)	−0.0057 (14)	0.0193 (17)	0.0078 (16)
C7	0.0368 (14)	0.0433 (14)	0.0485 (15)	0.0011 (11)	−0.0027 (13)	−0.0063 (12)
C8	0.0412 (14)	0.0332 (13)	0.0416 (14)	−0.0015 (10)	−0.0005 (12)	−0.0017 (10)
Cl1	0.1194 (9)	0.0689 (6)	0.0645 (6)	−0.0233 (5)	0.0383 (6)	−0.0211 (4)
Cl3	0.0991 (8)	0.0439 (4)	0.0973 (7)	−0.0162 (4)	0.0522 (6)	0.0022 (4)
Cl2	0.0527 (5)	0.0816 (6)	0.1141 (8)	0.0127 (4)	0.0146 (5)	0.0168 (6)
N1	0.0462 (15)	0.0550 (16)	0.0728 (18)	0.0068 (12)	0.0062 (14)	−0.0033 (13)
N2	0.0482 (13)	0.0234 (10)	0.0584 (14)	0.0020 (9)	0.0148 (11)	0.0000 (9)
O1	0.0560 (12)	0.0243 (9)	0.0767 (14)	−0.0014 (8)	0.0169 (11)	−0.0020 (8)
O2	0.0786 (18)	0.0568 (15)	0.122 (2)	0.0245 (13)	0.0300 (16)	0.0152 (15)
O3	0.0544 (15)	0.0901 (18)	0.125 (2)	0.0202 (13)	0.0345 (16)	0.0105 (17)

C1—C2	1.552 (4)	C5—C6	1.374 (4)
C1—Cl3	1.756 (3)	C5—H5	0.9300
C1—Cl1	1.766 (3)	C6—C7	1.374 (4)
C1—Cl2	1.777 (3)	C6—H6	0.9300
C2—O1	1.209 (3)	C7—C8	1.380 (4)
C2—N2	1.348 (3)	C7—N1	1.476 (4)
C3—C8	1.385 (3)	C8—H8A	0.9300
C3—C4	1.395 (3)	N1—O2	1.207 (3)
C3—N2	1.417 (3)	N1—O3	1.223 (4)
C4—C5	1.372 (4)	N2—H2N	0.8600
C4—H4	0.9300
C2—C1—Cl3	110.05 (18)	C6—C5—H5	119.6
C2—C1—Cl1	110.3 (2)	C7—C6—C5	117.9 (3)
Cl3—C1—Cl1	109.88 (16)	C7—C6—H6	121.1
C2—C1—Cl2	109.17 (19)	C5—C6—H6	121.1
Cl3—C1—Cl2	108.75 (18)	C6—C7—C8	123.4 (3)
Cl1—C1—Cl2	108.65 (15)	C6—C7—N1	118.5 (3)
O1—C2—N2	125.5 (2)	C8—C7—N1	118.1 (2)
O1—C2—C1	120.9 (2)	C7—C8—C3	117.7 (2)
N2—C2—C1	113.6 (2)	C7—C8—H8A	121.1
C8—C3—C4	119.8 (2)	C3—C8—H8A	121.1
C8—C3—N2	123.5 (2)	O2—N1—O3	123.6 (3)
C4—C3—N2	116.7 (2)	O2—N1—C7	118.5 (3)
C5—C4—C3	120.4 (3)	O3—N1—C7	117.8 (3)
C5—C4—H4	119.8	C2—N2—C3	126.5 (2)
C3—C4—H4	119.8	C2—N2—H2N	116.8
C4—C5—C6	120.8 (3)	C3—N2—H2N	116.8
C4—C5—H5	119.6
Cl3—C1—C2—O1	−3.2 (4)	C6—C7—C8—C3	−0.6 (4)
Cl1—C1—C2—O1	−124.6 (3)	N1—C7—C8—C3	−179.1 (2)
Cl2—C1—C2—O1	116.1 (3)	C4—C3—C8—C7	−1.2 (4)
Cl3—C1—C2—N2	177.6 (2)	N2—C3—C8—C7	177.4 (2)
Cl1—C1—C2—N2	56.2 (3)	C6—C7—N1—O2	−176.5 (3)
Cl2—C1—C2—N2	−63.1 (3)	C8—C7—N1—O2	2.1 (4)
C8—C3—C4—C5	1.9 (5)	C6—C7—N1—O3	6.1 (4)
N2—C3—C4—C5	−176.8 (3)	C8—C7—N1—O3	−175.3 (3)
C3—C4—C5—C6	−0.8 (6)	O1—C2—N2—C3	1.3 (5)
C4—C5—C6—C7	−1.0 (6)	C1—C2—N2—C3	−179.5 (3)
C5—C6—C7—C8	1.8 (5)	C8—C3—N2—C2	18.2 (4)
C5—C6—C7—N1	−179.7 (3)	C4—C3—N2—C2	−163.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.93	2.32	2.870 (3)	117
C4—H4···O1i	0.93	2.59	3.345 (4)	138
N2—H2N···O1i	0.86	2.15	2.990 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.59	3.345 (4)	138
N2—H2N⋯O1i	0.86	2.15	2.990 (3)	164

Symmetry code: (i) .