N-(4-Chloro-2-nitro­phen­yl)-N-(methyl­sulfon­yl)acetamide

Muhammad Zia-ur-Rehman; Nosheen Akbar; Muhammad Nadeem Arshad; Islam Ullah Khan

doi:10.1107/S1600536808032157

. 2008 Oct 11;64(Pt 11):o2092. doi: 10.1107/S1600536808032157

N-(4-Chloro-2-nitrophenyl)-N-(methylsulfonyl)acetamide

Muhammad Zia-ur-Rehman ^a, Nosheen Akbar ^b,^*, Muhammad Nadeem Arshad ^c, Islam Ullah Khan ^c

PMCID: PMC2959785 PMID: 21580956

Abstract

The title compound, C₉H₉ClN₂O₅S, is of interest as a precursor to biologically active substituted quinolines and related compounds. The structure displays intermolecular C—H⋯O interactions. Each molecule is linked to two adjacent neighbours via weak centrosymmetric dimer-forming interactions, forming chains in the [101] direction.

Related literature

For synthesis and biological evaluation of sulfur-containing heterocyclic compounds, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶); Wen et al. (2005 ▶); Zhang, Xu, Wen et al. (2006 ▶). For related molecules, see: (Wen et al., 2006 ▶; Zhang, Xu, Zou et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₉H₉ClN₂O₅S
M _r = 292.70
Monoclinic,
a = 9.8071 (4) Å
b = 9.4310 (4) Å
c = 13.5679 (7) Å
β = 105.883 (2)°
V = 1207.00 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 296 (2) K
0.25 × 0.15 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.913, T _max = 0.956
13383 measured reflections
2988 independent reflections
2077 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.104
S = 1.02
2981 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032157/ez2142sup1.cif

e-64-o2092-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032157/ez2142Isup2.hkl

e-64-o2092-Isup2.hkl^{(146.3KB, hkl)}

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
C2—H2⋯O5ⁱ	0.93	2.55	3.404 (3)	153
C9—H9B⋯O3ⁱⁱ	0.96	2.58	3.521 (3)	169

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors are grateful to the PCSIR Laboratories Complex, Lahore, Pakistan, for provision of the necessary chemicals, and the Higher Education Commission of Pakistan for the purchase of the diffractometer.

supplementary crystallographic information

Comment

N-(Substituted phenyl)acetamides are well known for their importance as intermediates in organic synthesis. They are used as precursors for the synthesis of many heterocyclic compounds, e.g. 2,5-piperazinedione (Wen et al., 2006), (quinolin-8-yloxy)acetamide (Zhang, Xu, Wen et al., 2006) and 2,2-(1,3,4-thiadiazolyl-2,5-dithio)diacetamide (Wen et al., 2005). In the present paper, the structure of N-(4-chloro-2-nitrophenyl)-N-(methylsulfonyl)acetamide (I) has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2005, 2006, 2007, 2008).

In the molecule of I (Fig. 1), the bond lengths and bond angles are similar to those in related molecules (Wen et al., 2006; Zhang, Xu, Zou et al., 2006) and are within normal ranges (Allen et al., 1987). The nitro group is slightly twisted out of the plane of the benzene ring, as indicated by O1—N1—C3—C2 and O2—N1—C3—C2 torsion angles of -16.7 (3) and 160.9 (2)°, respectively. Each molecule is linked to its neighbour via a centrosymmetric head-to-tail interaction between the methyl hydrogen H9B and the carbonyl oxygen [C9—H9B···O3]. Adjacent pairs of these molecules are then linked into chains via intermolecular [C2—H5···O5] interactions along the [101] direction (Table 1 and Fig. 2).

Experimental

A mixture of N-(4-chloro-2-nitrophenyl)methane sulfonamide (2.507 g; 10.0 mmoles) and acetic anhydride (10.0 ml) was heated to reflux for half an hour and then poured over crushed ice. Resultant solids were then washed with cold water and dried under reduced pressure. Yellow crystals were obtained by slow evaporation of an ethanolic solution over a period of two days.