2-Nitro-N-propyl­benzamide

Li-Hua Guo; Hai-Jun Tan; Ji-Kui Wang; Jin-Tang Wang

doi:10.1107/S1600536809020728

. 2009 Jun 6;65(Pt 7):o1488. doi: 10.1107/S1600536809020728

2-Nitro-N-propylbenzamide

Li-Hua Guo ^a, Hai-Jun Tan ^a, Ji-Kui Wang ^a,^*, Jin-Tang Wang ^a

PMCID: PMC2969221 PMID: 21582789

Abstract

The title compound, C₁₀H₁₂N₂O₃, contains three molecules in the asymmetric unit. In the crystal structure, intermolecular N—H⋯O interactions link the molecules into chains along the b axis. The crystal structure is consolidated by weak C—H⋯π interactions.

Related literature

The title compound is an agent for treating and preventing pains, see: Goodman & Serafini (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₀H₁₂N₂O₃
M _r = 208.22
Monoclinic,
a = 15.835 (3) Å
b = 9.3910 (19) Å
c = 23.618 (5) Å
β = 108.35 (3)°
V = 3333.6 (12) Å³
Z = 12
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.973, T _max = 0.991
6289 measured reflections
6056 independent reflections
2855 reflections with I > 2σ(I)
R _int = 0.060
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.188
S = 1.00
6056 reflections
388 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, Il. DOI: 10.1107/S1600536809020728/at2796sup1.cif

e-65-o1488-sup1.cif^{(27KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020728/at2796Isup2.hkl

e-65-o1488-Isup2.hkl^{(296.5KB, 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
N1—H1A⋯O4ⁱ	0.86	2.02	2.854 (5)	163
N3—H3C⋯O1	0.86	1.98	2.840 (4)	177
N5—H5A⋯O7ⁱⁱ	0.86	2.04	2.843 (4)	154
C6—H6A⋯Cg2	0.93	2.86	3.751 (5)	162

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Symmetry codes: (i) Inline graphic ; (ii) . Cg2 is the centroid of the C15–C20 ring.

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound is a kind of medicament for treating and preventing pains, and traumatic injuries such as traumatic brain injury and acute spinal cord injury (Goodman & Serafini, 2004). We herein report the crystal structure of the title compound (I).

In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The title compound crystallized in the monolinic space group P2₁/c, with three independent molecules (A, B and C) in the asymmetric unit.

In the crystal structure, intermolecular N—H···O interactions (Table 1) link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure. The crystal structure is consolidated by C—H···π hydrogen-bonding interactions (Table 1).

Experimental

2-Nitro-N-propylbenzamide were dissolved in DMF (50 mL). The solution was then poured to ice water. The crystalline product was isolated by filtration, washed with water (600 ml), dried and give the product 1.8 g. The crystals of (I) were obtained by evaporating the acetone slowly at room temperature for about 14 d.