(2-Chloro-3,5-dinitro­phen­yl)(piperidin-1-yl)methanone

Xun Luo; Yun-Chuang Huang; Chao Gao; Luo-Ting Yu

doi:10.1107/S1600536811011469

. 2011 Apr 7;67(Pt 5):o1066. doi: 10.1107/S1600536811011469

(2-Chloro-3,5-dinitrophenyl)(piperidin-1-yl)methanone

Xun Luo ^a,^*, Yun-Chuang Huang ^a, Chao Gao ^a, Luo-Ting Yu ^a

PMCID: PMC3089352 PMID: 21754392

Abstract

In the title compound, C₁₂H₁₂ClN₃O₅, the piperidine ring adopts a chair conformation. One of the nitro groups is almost coplanar with the aromatic ring [O—N—C—C = −1.4 (2)°], whereas the other one is significantly twisted out of the ring plane [O—N—C—C = 34.7 (2)°]. The crystal packing is stabilized by intermolecular π–π stacking interactions with centroid–centroid distances of 3.579 (3) Å.

Related literature

For the biological activity of benzamide derivatives, see: Christophe et al. (2009 ▶).

Experimental

Crystal data

C₁₂H₁₂ClN₃O₅
M _r = 313.70
Orthorhombic,
a = 10.7864 (3) Å
b = 11.1264 (3) Å
c = 21.9775 (5) Å
V = 2637.60 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 150 K
0.40 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T _min = 0.979, T _max = 1.0
6722 measured reflections
2696 independent reflections
2240 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.077
S = 1.05
2696 reflections
238 parameters
All H-atom parameters refined
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011469/bt5492sup1.cif

e-67-o1066-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011469/bt5492Isup2.hkl

e-67-o1066-Isup2.hkl^{(132.5KB, hkl)}

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

Acknowledgments

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

supplementary crystallographic information

Comment

Benzamide derivatives are of great importance owing to their antibacterial properties (Christophe et al., 2009). The title compound is one of the key intermediates in our synthetic investigations of antibacterial drugs.

The piperidine ring adopts a chair conformation. As shown in Fig.1, the amide group forms a dihedral angles of 75.96 (5)° and 51.61 (9)° with the benzene ring and the piperidine ring, respectively. The crystal packing is strengthened by intermolecular π–π stacking interaction with centroid–centroid distances of 3.579 (3) Å.

Experimental

A solution of 3.42 g (12.9 mmol) of 2-chloro-3,5-dinitrobenzoyl chloride in 20 ml of dichloromethane was added to a solution of 1.097 g (12.9 mmol) piperidine with a catalyst of 1.82 g (17.9 mmol) triethylamine. The mixture was stirred for 2 h at room temperature and extracted with water and dichloromethane, then the organic solvent was evaporated and the title compound was recrystallized from ethanol (yield 3.24 g, 80%). Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of ethyl acetate.