2-Meth­oxy-N-[(S)-3-methyl­butan-2-yl]-6-{[(S)-3-methyl­butan-2-yl]amino}-3,5-dinitro­benzamide

Xuefen Wu; Xi Chen; Yimin Hou

doi:10.1107/S1600536811049749

. 2011 Nov 30;67(Pt 12):o3482. doi: 10.1107/S1600536811049749

2-Methoxy-N-[(S)-3-methylbutan-2-yl]-6-{[(S)-3-methylbutan-2-yl]amino}-3,5-dinitrobenzamide

Xuefen Wu ^a,^*, Xi Chen ^b, Yimin Hou ^a

PMCID: PMC3239106 PMID: 22199954

Abstract

The title compound, C₁₈H₂₈N₄O₆, crystallizes with two molecules in the asymmetric unit which differ slightly in conformation. The dihedral angle between the amide plane and the benzene ring are 72.6 (2) and 66.8 (2)° in the two molecules. A strong intramolecular N—H⋯O hydrogen bond between the amino and nitro groups occurs in each molecule. The crystal structure features two symmetry-independent polymeric chains along [010] generated by N—H⋯O hydrogen bonds between the amide groups.

Related literature

For aromatic molecules with amide, nitro and alkoxy groups and their use in medicinal chemistry, see: Neft & Farley (1971 ▶); Sykes et al. (1999 ▶).

Experimental

Crystal data

C₁₈H₂₈N₄O₆
M _r = 396.44
Monoclinic,
a = 21.1662 (16) Å
b = 9.8317 (7) Å
c = 22.565 (2) Å
β = 117.163 (1)°
V = 4177.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.68 × 0.22 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.938, T _max = 0.990
12447 measured reflections
5062 independent reflections
2956 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.188
S = 0.99
5062 reflections
505 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049749/gk2433sup1.cif

e-67-o3482-sup1.cif^{(29KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049749/gk2433Isup2.hkl

e-67-o3482-Isup2.hkl^{(247.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811049749/gk2433Isup3.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
N3—H3A⋯O7ⁱ	0.86	2.12	2.967 (4)	168
N6—H6A⋯O14ⁱⁱ	0.86	2.05	2.906 (4)	177
N7—H7B⋯O3	0.86	1.99	2.619 (6)	129
N8—H8D⋯O11	0.86	2.08	2.654 (5)	123

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

Acknowledgments

The authors thank Henan University of Traditional Chinese Medicine for supporting this study.

supplementary crystallographic information

Comment

Amide, nitro and alkoxy groups exist in many active compounds, and have been shown to affect biological activity of compounds in varying degrees (Neft & Farley, 1971; Sykes et al., 1999). We synthesised the title compound and plan to examine its function as potential drug or as a prodrug.

The dihedral angle between the amide plane and the benzene ring in the two molecules are 72.6 (2)° and 66.8 (2)°, respectively. The molecules are linked by intermolecular N—H···O hydrogen bonding, forming one-dimensional infinite zigzag chain in the [010] directions, in which the amide H atom acts as a donor and the carbonyl group act as acceptor (Fig.2).

Experimental

To a solution of (S)-3-methylbutan-2-amine (0.45 g, 5 mmol)) in dry dichloromethane (30 ml) and triethylamine (1 mL) was added 2,6-dimethoxy-3,5-dinitrobenzoyl chloride (0.58 g, 2 mmol) at 0°C. The mixture was stirred at room temperature for another 2 h. The residue was subjected to chromatography (petroleum ether/acetone, 5:1) to provide the product as a yellow solid (80.8 mg, 10.2%). The crystal of the title compound was grown from ethyl acetate.