2,2,2-Trichloro-N-(3-nitro­phen­yl)acetamide

Abstract

In the title compound, C₈H₅Cl₃N₂O₃, the dihedral angle between the nitro­phenyl ring and the acetamide group is 5.47 (6)°. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules 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 _r = 283.49

• Orthorhombic,

• a = 11.5164 (8) Å

• b = 10.1427 (5) Å

• c = 19.9054 (11) Å

• V = 2325.1 (2) ų

• 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

• Δρ_max = 0.46 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

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

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) .

supplementary crystallographic information

Comment

In view of earlier studies and interest owing to the biological activity of acetamide (Khan et al., 2010; Tahir & Shad, 2011), we report herein the crystal structure of the title compound. In the title compound, the nitro phenyl ring makes a dihedral angle of 5.47 (6)° with acetamide group. Bond lengths and angles are within the normal ranges and are comparable with a related structure (Rosli et al., 2007). In the crystal, an S(6) ring motif (Bernstein et al., 1995) is formed via intramolecular C8—H8A···O1 hydrogen bond (Table 1). The C—H···O and C—H···N hydrogen bonding intractions (Table 1 and Figure 2) result in bifurcated bonds and link the molecules into chains along the b-axis.

Experimental

3-Nitroaniline (1.0 g, 0.0072 mmol) was dissolved in 2M hydrochloric acid (5.0 ml), and added a little crushed ice. A solution of hydrated sodium acetate (5.0 g) in 25 ml of water was introduced, followed by trichloroacetic anhydride (4.5 g, 0.01457 mol). The mixture was shaken in the cold until the smell of trichloroacetic anhydride disappeared. The title compound was collected by filtration and recrystallized from an aqueous ethanol (75%) solution; yield: 1.52 g (75%), m.p. 376.15–378.15 K.

Refinement

The H atoms were placed at calculated positions in the riding model approximation with N—H = 0.86 and C—H = 0.93 Å, and U_iso(H) = 1.2U_eq(N/C).

Figures

Fig. 1.

ORTEP (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.

Fig. 2.

A unit cell packing of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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

Symmetry code: (i) −x+3/2, y−1/2, z.