N-(2-Nitro­phen­yl)thio­phene-2-carbox­amide

Rodolfo Moreno-Fuquen; Alexis Azcárate; Alan R Kennedy

doi:10.1107/S160053681400912X

. 2014 Apr 26;70(Pt 5):o613. doi: 10.1107/S160053681400912X

N-(2-Nitrophenyl)thiophene-2-carboxamide

Rodolfo Moreno-Fuquen ^a,^*, Alexis Azcárate ^a, Alan R Kennedy ^b

PMCID: PMC4011230 PMID: 24860404

Abstract

The title compound, C₁₁H₈N₂O₃S, shows two molecules per asymmetric unit, with the dihedral angles between the benzene and thiophene rings of 13.53 (6) and 8.50 (5)° being a notable difference between them. An intramolecular N—H⋯O hydrogen-bond in each molecule generates an S(6) ring motif. The crystal packing shows no classical hydrogen bonds with the molecules being packed to form weak C—H⋯O and C—H⋯S interactions leading to R ₂ ²(9) and R ₄ ⁴(25) rings which are edge-shared, giving layers parallel to (010).

Related literature

For the antibacterial and antifungal activity of amide compounds, see: Aytemir et al. (2003 ▶); Hrelia et al. (1995 ▶). For a similar compound, see: Moreno-Fuquen et al. (2013 ▶). For hydrogen-bonding information, see: Nardelli (1995 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C₁₁H₈N₂O₃S
M _r = 248.25
Monoclinic,
a = 11.6359 (3) Å
b = 13.2501 (3) Å
c = 17.7412 (4) Å
β = 129.898 (1)°
V = 2098.47 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 123 K
0.28 × 0.15 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.953, T _max = 1.000
10418 measured reflections
5093 independent reflections
4012 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.116
S = 1.04
5093 reflections
315 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681400912X/tk5309sup1.cif

e-70-0o613-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400912X/tk5309Isup2.hkl

e-70-0o613-Isup2.hkl^{(244.4KB, hkl)}

Click here for additional data file.^{(4.2KB, cml)}

Supporting information file. DOI: 10.1107/S160053681400912X/tk5309Isup3.cml

CCDC reference: 998902

Additional supporting information: 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—H1N⋯O2	0.81 (3)	1.96 (3)	2.634 (2)	140 (3)
N3—H3N⋯O5	0.84 (2)	1.93 (2)	2.616 (2)	138 (2)
C1—H1⋯O4ⁱ	0.95	2.50	3.209 (3)	131
C8—H8⋯O5ⁱⁱ	0.95	2.52	3.248 (3)	133
C19—H19⋯O2ⁱⁱⁱ	0.95	2.63	3.377 (3)	136
C11—H11⋯S2ⁱⁱⁱ	0.95	2.92	3.732 (2)	144
C22—H22⋯S1ⁱⁱ	0.95	2.84	3.689 (2)	149
C12—H12⋯O1^iv	0.95	2.47	3.198 (3)	133

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

Acknowledgments

RMF thanks the Universidad del Valle, Colombia, for partial financial support.

supplementary crystallographic information

1. Introduction

2. Experimental

2.1. Synthesis and crystallization

The reagents and solvents for the synthesis were obtained from the Aldrich Chemical Co., and were used without additional purification. The title molecule was synthesized using equimolar quantities of 2-thiophenecarbonyl chloride (0.376 g., 2.565 mmol) and 2-nitroaniline (0.354 g). The reagents were dissolved in 10 mL of acetonitrile and the solution was taken to reflux in constant stirring for 1 hour. Yellow crystals of good quality were obtained after leaving the solvent to evaporate. M.pt: 397 (1) K.

2.2. Refinement

All H-atoms were positioned at geometrically idealized positions with a C—H distance of 0.95 Å and U_iso(H) = 1.2U_eq of the atoms to which they were bonded. The H1N and H3N atoms were found from Fourier maps and were refined freely.

3. Results and discussion

The present compound forms part of a systematic work on N-aromatic amides in our research group. Antibacterial and antifungal activities of different carboxyamide derivatives have been reported (Aytemir et al., 2003). Derivatives of thiophene carboxanilide compounds present genotoxicity in bacterial mammalian and human cells (Hrelia et al., 1995). In the synthesis of the amides, the 2-nitroaniline is taken as a template, in order to study the structural changes and the supramolecular behavior by the reaction of different ligands with this precursor (Moreno-Fuquen et al., 2013). With this aim, the synthesis of N-(2-nitrophenyl)thiophene-2-carboxamide (I) was undertaken. The structure of N-(2-nitrophenyl)furan-2-carboxamide (2NPFC), (Moreno-Fuquen et al., 2013), a similar compound, was taken to compare with the structural parameters of (I).

The title compound shows two molecules (A and B) per asymmetric unit (see Fig. 1). Compound (I) exhibits dihedral angles between the benzene and thiophene rings of 13.53 (6)° and 8.50 (5)° for A and B, respectively. These dihedral angles are very similar to the value presented in the (2NPFC) system [9.71 (5)°]. The other bond lengths and bond angles agree closely with those values presented in its homologous amide (2NPFC), except for the C—S distances, which for obvious reasons are different on the furan rings. The nitro groups form dihedral angles with the adjacent benzene ring of 15.44 (4) and 16.07 (6)° for O2—N2—O3 and O5—N4—O6, respectively.

The crystal packing shows no classical hydrogen bonds and the molecules are packed forming weak C—H···O and C—H···S interactions and they are propagated parallel to (010) (see Fig. 2). According to the graph-set assignment, the intramolecular hydrogen-bond pattern generates a S(6) ring motif (Etter, 1990) (see Table 1). The C8 and C11 atoms of the phenyl ring and C1 atom of the thiophene ring at (x, y, z), act as hydrogen-bond donors to the nitro O5 atom at (x, -y+3/2, +z+1/2), to the S2 atom at (x-1, -y+3/2, +z-1/2) and to the carbonyl atom O4 at (x, -y+3/2, +z-1/2), respectively. Additionally, the C19 and C22 atoms of the benzene ring and C12 atom of the thiophene ring at (x, y, z) act as hydrogen-bond donors to the nitro O2 atom at (x-1, -y+3/2, +z-1/2), to the S1 atom at (x, -y+3/2, +z+1/2) and to the carbonyl O1 atom at (x+1, -y+3/2, +z+1/2), respectively, (see Table 1; Nardelli, 1995). All these interactions form an R²₂(9) and R⁴₄(25) edge-fused ring which are running parallel to (010) (see Fig. 2).