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

Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S160053680706881X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o382

doi:10.1107/S160053680706881X

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

B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 27 December 2007; accepted 31 December 2007; online 9 January 2008)

The conformation of the N—H bond in the structure of the title compound (3NPDCA), C₈H₆Cl₂N₂O₃, is anti to the meta-nitro group, similar to that in the structures of 2-chloro-N-(3-nitrophenyl)acetamide (3NPCA) and 2,2,2-trichloro-N-(3-nitrophenyl)acetamide (3NPTCA), and the meta-chloro group in 2,2-dichloro-N-(3-chlorophenyl)acetamide (3CPDCA). The geometric parameters of 3NPDCA are similar to those of 2,2-dichloro-N-phenylacetamide, 3CPDCA, 3NPCA, 3NPTCA and other acetanilides. Intermolecular N—H⋯O hydrogen bonds link the molecules into chains running along the b axis.

Related literature

For related literature, see: Gowda & Weiss (1994 ); Gowda et al. (2000 , 2006 , 2007 ).

Experimental

Crystal data

C₈H₆Cl₂N₂O₃
M_r = 249.05
Orthorhombic, P b c a
a = 9.6092 (6) Å
b = 10.6487 (7) Å
c = 19.868 (1) Å
V = 2033.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 299 (2) K
0.60 × 0.52 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Version 1.171.32.5. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.706, T_max = 0.865
11267 measured reflections
2072 independent reflections
1614 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.098
S = 1.10
2072 reflections
155 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.833 (16)	2.081 (17)	2.907 (2)	171 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Version 1.171.26. Oxford Diffraction Ltd. Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Version 1.171.32.5. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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: SHELXS97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706881X/dn2307sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680706881X/dn2307Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of ring and side chain substitutions on the solid state structures of acetanilides (Gowda et al., 2000, 2006, 2007), in the present work, the crystal structure of 2,2-dichloro-N- (3-nitrophenyl)-acetamide (3NPDCA) has been determined to explore the effects of polar substituent groups on the structures of N-aromatic amides. The conformation of the N—H bond in the structure of 3NPDCA (Fig.1) is anti to the meta nitro group, similar to that in the structure of 2-chloro-N-(3-nitrophenyl)-acetamide (3NPCA) (Gowda et al., 2007) and 2,2,2-trichloro-N-(3-nitrophenyl)-acetamide (3NPTCA)(Gowda et al., 2000) and meta chloro group in 2,2-dichloro-N-(3-chlorophenyl)-acetamide (3CPDCA)(Gowda et al., 2006). The geometric parameters in 3NPDCA are similar to those of 2,2-dichloro-N-(phenyl)-acetamide, 3CPDCA, 3NPCA, 3NPTCA and other acetanilides. The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains running along the b axis (Fig. 2).

Related literature top

For related literature, see: Gowda & Weiss (1994); Gowda et al. (2000, 2006, 2007).

Experimental top

The title compound was prepared similar to the literature method (Gowda and Weiss, 1994). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NQR spectra (Gowda and Weiss, 1994). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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: SHELXS97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the hydrogen bonding as dashed lines.H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) x - 1/2, 1/2 - y,1 - z]

2,2-Dichloro-N-(3-nitrophenyl)acetamide top

Crystal data top

C₈H₆Cl₂N₂O₃	F(000) = 1008
M_r = 249.05	D_x = 1.627 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4893 reflections
a = 9.6092 (6) Å	θ = 2.8–27.8°
b = 10.6487 (7) Å	µ = 0.63 mm⁻¹
c = 19.868 (1) Å	T = 299 K
V = 2033.0 (2) Å³	Prism, yellow
Z = 8	0.60 × 0.52 × 0.24 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2072 independent reflections
Radiation source: fine-focus sealed tube	1614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Rotation method data acquisition using ω and ϕ scans.	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007)	h = −12→11
T_min = 0.706, T_max = 0.865	k = −11→13
11267 measured reflections	l = −24→20

Refinement top

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0385P)² + 1.4567P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.044
2072 reflections	Δρ_max = 0.35 e Å⁻³
155 parameters	Δρ_min = −0.36 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0230 (13)

Crystal data top

C₈H₆Cl₂N₂O₃	V = 2033.0 (2) Å³
M_r = 249.05	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.6092 (6) Å	µ = 0.63 mm⁻¹
b = 10.6487 (7) Å	T = 299 K
c = 19.868 (1) Å	0.60 × 0.52 × 0.24 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2072 independent reflections
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007)	1614 reflections with I > 2σ(I)
T_min = 0.706, T_max = 0.865	R_int = 0.022
11267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.35 e Å⁻³
2072 reflections	Δρ_min = −0.36 e Å⁻³
155 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.03253 (19)	0.14098 (18)	0.60262 (10)	0.0344 (4)
C2	0.1408 (2)	0.05696 (19)	0.61012 (11)	0.0365 (4)
H2	0.204 (2)	0.043 (2)	0.5757 (12)	0.044*
C3	0.1543 (2)	−0.00244 (19)	0.67144 (11)	0.0380 (5)
C4	0.0653 (2)	0.0166 (2)	0.72466 (11)	0.0453 (5)
H4	0.075 (3)	−0.025 (2)	0.7632 (14)	0.054*
C5	−0.0418 (2)	0.1009 (2)	0.71576 (12)	0.0490 (6)
H5	−0.103 (3)	0.122 (2)	0.7521 (14)	0.059*
C6	−0.0584 (2)	0.1632 (2)	0.65542 (11)	0.0426 (5)
H6	−0.131 (3)	0.220 (2)	0.6503 (13)	0.051*
C7	0.1102 (2)	0.24984 (19)	0.50064 (11)	0.0357 (4)
C8	0.0552 (2)	0.3297 (2)	0.44287 (11)	0.0398 (5)
H8	−0.034 (3)	0.352 (2)	0.4488 (11)	0.048*
N1	0.01034 (17)	0.20745 (17)	0.54149 (9)	0.0381 (4)
H1N	−0.0711 (18)	0.227 (2)	0.5320 (12)	0.046*
N2	0.2700 (2)	−0.09083 (18)	0.67926 (10)	0.0491 (5)
O1	0.23372 (15)	0.22854 (16)	0.50684 (9)	0.0532 (5)
O2	0.3669 (2)	−0.08426 (19)	0.63930 (10)	0.0664 (5)
O3	0.2672 (2)	−0.16436 (19)	0.72637 (10)	0.0759 (6)
Cl1	0.15452 (6)	0.46874 (5)	0.43763 (3)	0.0529 (2)
Cl2	0.06927 (8)	0.24208 (7)	0.36778 (3)	0.0661 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0270 (9)	0.0403 (10)	0.0360 (10)	−0.0056 (8)	−0.0003 (8)	0.0025 (8)
C2	0.0334 (10)	0.0388 (10)	0.0374 (10)	−0.0034 (8)	−0.0001 (8)	0.0008 (8)
C3	0.0363 (10)	0.0346 (10)	0.0430 (11)	−0.0033 (8)	−0.0046 (9)	0.0017 (8)
C4	0.0494 (13)	0.0483 (12)	0.0382 (11)	−0.0071 (10)	−0.0014 (10)	0.0065 (10)
C5	0.0460 (13)	0.0583 (14)	0.0428 (12)	−0.0043 (11)	0.0103 (10)	−0.0006 (10)
C6	0.0311 (10)	0.0487 (12)	0.0479 (12)	−0.0012 (9)	0.0036 (9)	0.0014 (10)
C7	0.0272 (9)	0.0389 (10)	0.0409 (10)	0.0013 (8)	−0.0009 (8)	0.0020 (8)
C8	0.0307 (10)	0.0479 (12)	0.0409 (11)	0.0006 (9)	−0.0001 (9)	0.0045 (9)
N1	0.0239 (8)	0.0503 (10)	0.0401 (9)	0.0018 (7)	−0.0002 (7)	0.0076 (8)
N2	0.0507 (11)	0.0446 (10)	0.0521 (11)	0.0028 (9)	−0.0091 (10)	0.0056 (9)
O1	0.0258 (7)	0.0698 (11)	0.0641 (10)	0.0050 (7)	0.0044 (7)	0.0272 (8)
O2	0.0606 (11)	0.0718 (12)	0.0668 (12)	0.0250 (10)	0.0086 (10)	0.0109 (10)
O3	0.0786 (13)	0.0713 (12)	0.0778 (13)	0.0122 (11)	−0.0056 (11)	0.0361 (11)
Cl1	0.0558 (4)	0.0395 (3)	0.0635 (4)	−0.0031 (2)	−0.0001 (3)	0.0064 (2)
Cl2	0.0740 (5)	0.0778 (5)	0.0467 (4)	−0.0200 (4)	−0.0084 (3)	−0.0116 (3)

Geometric parameters (Å, º) top

C1—C2	1.380 (3)	C6—H6	0.93 (3)
C1—C6	1.386 (3)	C7—O1	1.215 (2)
C1—N1	1.422 (2)	C7—N1	1.335 (3)
C2—C3	1.379 (3)	C7—C8	1.523 (3)
C2—H2	0.93 (2)	C8—Cl1	1.764 (2)
C3—C4	1.376 (3)	C8—Cl2	1.765 (2)
C3—N2	1.464 (3)	C8—H8	0.90 (3)
C4—C5	1.377 (3)	N1—H1N	0.833 (16)
C4—H4	0.89 (3)	N2—O3	1.220 (3)
C5—C6	1.380 (3)	N2—O2	1.226 (3)
C5—H5	0.96 (3)

C2—C1—C6	120.30 (19)	C1—C6—H6	120.0 (16)
C2—C1—N1	121.86 (17)	O1—C7—N1	125.26 (19)
C6—C1—N1	117.83 (18)	O1—C7—C8	121.32 (19)
C3—C2—C1	117.65 (19)	N1—C7—C8	113.42 (17)
C3—C2—H2	120.9 (15)	C7—C8—Cl1	108.99 (14)
C1—C2—H2	121.5 (15)	C7—C8—Cl2	108.35 (15)
C4—C3—C2	123.5 (2)	Cl1—C8—Cl2	110.62 (12)
C4—C3—N2	119.03 (19)	C7—C8—H8	112.2 (15)
C2—C3—N2	117.42 (19)	Cl1—C8—H8	107.9 (16)
C3—C4—C5	117.6 (2)	Cl2—C8—H8	108.8 (15)
C3—C4—H4	121.6 (17)	C7—N1—C1	125.44 (17)
C5—C4—H4	120.8 (17)	C7—N1—H1N	116.8 (17)
C4—C5—C6	120.8 (2)	C1—N1—H1N	117.5 (17)
C4—C5—H5	120.9 (16)	O3—N2—O2	123.4 (2)
C6—C5—H5	118.2 (16)	O3—N2—C3	118.5 (2)
C5—C6—C1	120.2 (2)	O2—N2—C3	118.10 (18)
C5—C6—H6	119.8 (16)

C6—C1—C2—C3	−0.2 (3)	N1—C7—C8—Cl1	131.85 (17)
N1—C1—C2—C3	179.62 (18)	O1—C7—C8—Cl2	71.9 (2)
C1—C2—C3—C4	0.8 (3)	N1—C7—C8—Cl2	−107.71 (18)
C1—C2—C3—N2	−179.58 (18)	O1—C7—N1—C1	6.6 (4)
C2—C3—C4—C5	−0.8 (3)	C8—C7—N1—C1	−173.76 (18)
N2—C3—C4—C5	179.6 (2)	C2—C1—N1—C7	−35.6 (3)
C3—C4—C5—C6	0.1 (3)	C6—C1—N1—C7	144.2 (2)
C4—C5—C6—C1	0.5 (3)	C4—C3—N2—O3	15.6 (3)
C2—C1—C6—C5	−0.4 (3)	C2—C3—N2—O3	−164.0 (2)
N1—C1—C6—C5	179.8 (2)	C4—C3—N2—O2	−162.0 (2)
O1—C7—C8—Cl1	−48.5 (3)	C2—C3—N2—O2	18.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (2)	2.08 (2)	2.907 (2)	171 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₆Cl₂N₂O₃
M_r	249.05
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	299
a, b, c (Å)	9.6092 (6), 10.6487 (7), 19.868 (1)
V (Å³)	2033.0 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.60 × 0.52 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector
Absorption correction	Multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007)
T_min, T_max	0.706, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	11267, 2072, 1614
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.098, 1.10
No. of reflections	2072
No. of parameters	155
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.833 (16)	2.081 (17)	2.907 (2)	171 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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