N-(2-Nitro­phen­yl)furan-2-carboxamide

Rodolfo Moreno-Fuquen; Alexis Azcárate; Alan R Kennedy; Denise Gilmour; Regina H De Almeida Santos

doi:10.1107/S1600536813026202

. 2013 Sep 28;69(Pt 10):o1592. doi: 10.1107/S1600536813026202

N-(2-Nitrophenyl)furan-2-carboxamide

Rodolfo Moreno-Fuquen ^a,^*, Alexis Azcárate ^a, Alan R Kennedy ^b, Denise Gilmour ^b, Regina H De Almeida Santos ^c

PMCID: PMC3790447 PMID: 24098266

Abstract

In the title furancarboxamide derivative, C₁₁H₈N₂O₄, the benzene and furan rings are rotated from the mean plane of the central fragment by 2.68 (5) and 7.03 (4)°, respectively. The nitro group forms a dihedral angle of 10.15 (5)° with the adjacent benzene ring. In the crystal, molecules are linked by weak C—H⋯O interactions, forming helical chains running along [010].

Related literature

For similar furancarboxamide compounds, see: Pavlović et al. (2004) ▶ and for similar 2-nitrophenylamino compounds, see: Glidewell et al. (2004 ▶). For hydrogen-bonding information, see: Nardelli (1995 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C₁₁H₈N₂O₄
M _r = 232.19
Monoclinic,
a = 7.0380 (5) Å
b = 12.8072 (9) Å
c = 11.3701 (9) Å
β = 97.819 (6)°
V = 1015.34 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 123 K
0.35 × 0.33 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer
4090 measured reflections
2649 independent reflections
1859 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.099
S = 1.04
2649 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 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/S1600536813026202/gg2129sup1.cif

e-69-o1592-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026202/gg2129Isup2.hkl

e-69-o1592-Isup2.hkl^{(111.6KB, hkl)}

Click here for additional data file.^{(4.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813026202/gg2129Isup3.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
C2—H2⋯O2ⁱ	0.95	2.55	3.3857 (18)	146

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

1. Comment

In the present work, the structure of N-(2-nitrophenyl)-2-furancarboxamide (I) has been determined as a part of a study undertaken in our research group on 2-nitrophenyl substituted carboxamides. Similar structures are known from the literature: 2-furancarboxanilide (2FCCA) [Pavlović et al., 2004] and ortho nitrophenylaminocarbonyl benzoic acid (2NPCB) [Glidewell et al., 2004] and they serve as a comparison to the values of the title system (I). The molecular structure of (I) is shown in Fig. 1. The central C4-C5(O2)-N1-C6 fragment of the molecule is essentially planar with a trans amide conformation. This behavior agrees with the behavior presented by 2NPCB system. The phenyl and furan rings are rotated from the mean plane of the central fragment by 2.68 (5)° and 7.03 (4)° respectively. The dihedral angle between the phenyl and furan rings is 9.71 (5)°. The nitro group forms a dihedral angle with the adjacent benzene ring of 10.15 (5)°. The formation of relatively strong intramolecular bonds between the central fragment and the furan ring, in some similar systems, can preserve the planarity of the 2-furancarboxamide moiety [Pavlović et al., 2004]. However, the planarity of the 2-furancarboxamide moiety is not preserved in the title compound. Relatively strong intramolecular interactions between the central fragment and nitrophenyl ring are observed. Indeed, the intramolecular interaction with the nitro group [N1···O3, 2.615 (1) Å and 135 (1)°] forces the central fragment to rotate, relative to the furan ring. The C1-C2 and C3-C4 within the furan ring, are within the expected range [1.341 Å; Allen et al., 2002]. Other bond distances in both furan and the phenyl rings are consistent with expected values (Allen et al., 2002). In the crystal, the molecules of (I) are linked by weak C2-H2···O2 interactions, forming one-dimensional helical chains running along [010], as shown in Fig. 2. The atom C2 of the furan ring at (x,y,z) acts as a hydrogen-bond donor to carbonyl atom O2 at (-x+1,+y+1/2,-z+3/2) (see Nardelli, 1995), forming a pattern specified as C(6) (Etter, 1990).

2. Experimental

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 furan-2-carbonyl chloride (0.202 g, 1.548 mmol) and 2-nitroaniline (0.144 g). The reagents were dissolved in 10 mL of acetonitrile and the solution was taken to reflux in constant stirring for 3 hours. Yellow crystals of good quality were obtained after leaving the solvent to evaporate. IR spectra were recorded on a FT—IR SHIMADZU IR-Affinity-1 spectrophotometer. m.p 388 (1) K. IR (KBr) 3310.91 cm^-1 (amide N-H), 3127.48 cm^-1 (aromatic C—H); 1679.05 cm^-1 (amide C=O); 1594.47 cm^-1, 1504.96 cm^-1 (-NO₂).