N-(2-Chloro-2-nitro-1-phenyl­prop­yl)-4-methyl­benzene­sulfonamide

Sanjun Zhi; Tengfei Li; Guanghui An; Yi Pan

doi:10.1107/S1600536807067712

. 2008 Jan 4;64(Pt 2):o357. doi: 10.1107/S1600536807067712

N-(2-Chloro-2-nitro-1-phenylpropyl)-4-methylbenzenesulfonamide

Sanjun Zhi ^a, Tengfei Li ^a, Guanghui An ^a, Yi Pan ^a,^*

PMCID: PMC2960443 PMID: 21201389

Abstract

In the title compound, C₁₆H₁₇ClN₂O₄S, the dihedral angle between the phenyl and benzene rings is 19.4 (2)°. The crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds, as well as by intra- and intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background, see Kemp (1991 ▶); Qui & Silverman (2000 ▶); Orlek & Stemp (1991 ▶), Han et al. (2007 ▶); Li et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₇ClN₂O₄S
M _r = 368.83
Orthorhombic,
a = 7.8254 (8) Å
b = 19.610 (2) Å
c = 22.533 (3) Å
V = 3457.8 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.901, T _max = 0.921
17527 measured reflections
3396 independent reflections
2467 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.125
S = 1.01
3396 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067712/at2518sup1.cif

e-64-0o357-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067712/at2518Isup2.hkl

e-64-0o357-Isup2.hkl^{(166.7KB, 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
C3—H3⋯O1	0.98	2.46	2.933 (4)	109
C3—H3⋯O3	0.98	2.42	2.779 (4)	101
C1—H1A⋯O2ⁱ	0.96	2.52	3.369 (4)	147
C1—H1B⋯O1ⁱⁱ	0.96	2.58	3.310 (4)	133
N2—H2A⋯O2ⁱ	0.89 (2)	2.32 (3)	3.141 (3)	153

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

Acknowledgments

This work was supported by the 863 High Technology Program (to YP). The research funds for YP from the Qing-Lan Program of Jiangsu Province and the Kua-Shi-Ji Program of the Education Ministry of China are also acknowledged.

supplementary crystallographic information

Comment

Since the vicinal haloamines are important building blocks in organic and medicinal chemistry, many attentions are attracted to the aminohalogenation reactions of functionalized alkenes (Kemp, 1991; Qui & Silverman, 2000). In recent years, many new aminohalogenation processes of several kinds of functionalized alkenes have been developed (Han et al., 2007), with the different nitrogen/halogen sources in the presence of metallic catalysts (Li et al., 2007). However, the aminohalogenation reactions of 2-nitro-propenyl benzene was not been well documented. Recently, we synthesized the title compound (I) from 2-nitro-propenyl benzene. As part of this study, we have undertaken the X-ray crystallographic analysis of (I) in order to elucidate the conformation and configuration of this product.

The bond lengths and angles in (I) are in good agree with expected values (Allen et al., 1987). The dihedral angle between the phenyl and benzene rings is 19.4 (2)°. The packing is stabilized by intermolecular N—H···O as well as intra and intermolecular C—H···O interactions in the crystal structure (Table 1).

Experimental

N-cChlorosuccinimide (400 mg, 3.0 mmol) was added into a solution of MnSO₄ (30.2 mg, 0.20 mmol), 1-benzyl-2-nitro-propene (163 mg, 1 mmol), tolunesulfonamide (513 mg, 3 mmol) and 4 Å molecular sieves (500 mg) in CH₂Cl₂ (5.0 ml) with nitrogen atmosphere. The resulting mixture was stirred at room temperature for 48 h. Reaction was quenched with saturated aqueous Na₂S₂O₃ solution. The solid precipitates were filtered off and washed with ethyl acetate (3 × 10 ml). The organic solution was concentrated and then purified via flash chromatography (ethyl acetate/ hexane, 1:4, v/v) provide the title compound (I) as white solid (276 mg) in yield of 75%. A colourless crystal of (I) for X-ray analysis was obtained by slow evaporation from ethyl acetate solution system.