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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Page o1592
doi:10.1107/S1600536813026202

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

Rodolfo Moreno-Fuquen,a* Alexis Azcárate,a Alan R. Kennedy,b Denise Gilmourb and Regina H. De Almeida Santosc

aDepartamento de Química – Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, bWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, and cInstituto de Química de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
*Correspondence e-mail: rodimo26@yahoo.es

(Received 17 September 2013; accepted 23 September 2013; online 28 September 2013)

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].

CCDC reference: 962601

Related literature

For similar furan­carboxamide compounds, see: Pavlović et al. (2004)[Pavlović, G., Tralić-Kulenović, V. & Popović, Z. (2004). Acta Cryst. E60, o631-o633.] and for similar 2-nitro­phenyl­amino compounds, see: Glidewell et al. (2004[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o120-o124.]). For hydrogen-bonding information, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C11H8N2O4

  • Mr = 232.19

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.099

  • S = 1.04

  • 2649 reflections

  • 158 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.26 e Å−3

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
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 962601

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813026202/gg2129sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813026202/gg2129Isup3.cml

checkCIF report


Comment top

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).

Related literature top

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 top

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).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H-atoms were positioned at geometrically idealized positions with C—H distance of 0.95 Å and Uiso(H) = 1.2 times Ueq of the C-atoms to which they were bonded. The coordinates of the H1N atom were refined.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top
[Figure 1] Fig. 1. Molecular conformation and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of helical chains which running along [010]. Symmetry code: (i) -x+1,+y+1/2,-z+3/2.
N-(2-Nitrophenyl)furan-2-carboxamide top
Crystal data top
C11H8N2O4F(000) = 480
Mr = 232.19Dx = 1.519 Mg m−3
Monoclinic, P21/cMelting point: 388(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.0380 (5) ÅCell parameters from 4090 reflections
b = 12.8072 (9) Åθ = 3.2–28.8°
c = 11.3701 (9) ŵ = 0.12 mm−1
β = 97.819 (6)°T = 123 K
V = 1015.34 (13) Å3Block, colourless
Z = 40.35 × 0.33 × 0.25 mm
Data collection top
Oxford Diffraction Xcalibur E
diffractometer		1859 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 28.8°, θmin = 3.2°
ω scansh = −9→8
4090 measured reflectionsk = −16→17
2649 independent reflectionsl = −7→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0395P)2 + 0.3116P]
where P = (Fo2 + 2Fc2)/3
2649 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C11H8N2O4V = 1015.34 (13) Å3
Mr = 232.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.0380 (5) ŵ = 0.12 mm−1
b = 12.8072 (9) ÅT = 123 K
c = 11.3701 (9) Å0.35 × 0.33 × 0.25 mm
β = 97.819 (6)°
Data collection top
Oxford Diffraction Xcalibur E
diffractometer		1859 reflections with I > 2σ(I)
4090 measured reflectionsRint = 0.016
2649 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.21 e Å−3
2649 reflectionsΔρmin = −0.26 e Å−3
158 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.33408 (13)0.25426 (7)0.47056 (8)0.0224 (2)
O20.39374 (15)0.05694 (8)0.69240 (9)0.0285 (3)
O30.10004 (16)0.07661 (8)0.27664 (9)0.0296 (3)
O40.02689 (18)−0.05720 (9)0.16525 (9)0.0374 (3)
N10.27083 (16)0.05097 (9)0.49375 (10)0.0188 (3)
N20.08218 (17)−0.01884 (10)0.26244 (10)0.0228 (3)
C10.3632 (2)0.35951 (11)0.48419 (14)0.0263 (3)
H10.34580.40890.42130.032*
C20.4197 (2)0.38338 (12)0.59859 (14)0.0270 (3)
H20.44820.45100.63060.032*
C30.4287 (2)0.28777 (12)0.66254 (13)0.0244 (3)
H30.46470.27880.74550.029*
C40.37595 (18)0.21213 (11)0.58195 (12)0.0190 (3)
C50.34973 (18)0.09956 (11)0.59629 (11)0.0190 (3)
C60.21685 (18)−0.05325 (11)0.47586 (12)0.0177 (3)
C70.12627 (18)−0.08875 (11)0.36456 (12)0.0191 (3)
C80.07181 (19)−0.19269 (12)0.34607 (13)0.0231 (3)
H80.0103−0.21450.27050.028*
C90.1070 (2)−0.26394 (11)0.43720 (13)0.0252 (3)
H90.0696−0.33480.42520.030*
C100.1977 (2)−0.23083 (11)0.54624 (13)0.0239 (3)
H100.2235−0.28000.60890.029*
C110.25161 (19)−0.12788 (11)0.56631 (12)0.0209 (3)
H110.3131−0.10750.64240.025*
H1N0.239 (2)0.0920 (14)0.4345 (16)0.036 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0275 (5)0.0196 (5)0.0194 (5)−0.0012 (4)0.0004 (4)0.0016 (4)
O20.0413 (6)0.0249 (6)0.0174 (5)−0.0017 (5)−0.0024 (4)0.0014 (4)
O30.0428 (7)0.0219 (6)0.0223 (6)0.0006 (5)−0.0018 (4)0.0005 (4)
O40.0554 (8)0.0350 (7)0.0188 (6)−0.0021 (6)−0.0061 (5)−0.0061 (5)
N10.0222 (6)0.0177 (6)0.0161 (6)0.0003 (5)0.0007 (4)0.0012 (5)
N20.0235 (6)0.0260 (7)0.0185 (6)0.0012 (5)0.0017 (5)−0.0020 (5)
C10.0279 (8)0.0188 (7)0.0318 (8)−0.0014 (6)0.0021 (6)0.0032 (6)
C20.0291 (8)0.0211 (7)0.0312 (8)−0.0040 (6)0.0048 (6)−0.0044 (6)
C30.0249 (7)0.0257 (8)0.0225 (7)−0.0044 (6)0.0033 (5)−0.0042 (6)
C40.0174 (6)0.0225 (7)0.0171 (7)0.0002 (5)0.0022 (5)0.0008 (5)
C50.0178 (6)0.0217 (7)0.0176 (7)0.0000 (6)0.0027 (5)−0.0007 (6)
C60.0144 (6)0.0193 (7)0.0200 (7)0.0006 (5)0.0047 (5)−0.0007 (5)
C70.0170 (6)0.0216 (7)0.0191 (7)0.0011 (5)0.0039 (5)−0.0011 (6)
C80.0196 (7)0.0268 (8)0.0237 (7)−0.0025 (6)0.0060 (5)−0.0070 (6)
C90.0249 (7)0.0199 (7)0.0322 (8)−0.0046 (6)0.0096 (6)−0.0034 (6)
C100.0245 (7)0.0211 (7)0.0274 (8)0.0000 (6)0.0079 (6)0.0042 (6)
C110.0203 (7)0.0227 (7)0.0196 (7)−0.0001 (6)0.0022 (5)−0.0004 (6)
Geometric parameters (Å, º) top
O1—C11.3690 (17)C3—C41.3503 (19)
O1—C41.3713 (16)C3—H30.9500
O2—C51.2231 (16)C4—C51.4653 (19)
O3—N21.2371 (16)C6—C111.4009 (19)
O4—N21.2235 (15)C6—C71.4125 (18)
N1—C51.3706 (17)C7—C81.393 (2)
N1—C61.3952 (17)C8—C91.378 (2)
N1—H1N0.860 (18)C8—H80.9500
N2—C71.4656 (18)C9—C101.381 (2)
C1—C21.343 (2)C9—H90.9500
C1—H10.9500C10—C111.3824 (19)
C2—C31.421 (2)C10—H100.9500
C2—H20.9500C11—H110.9500
C1—O1—C4105.83 (11)O2—C5—C4121.20 (13)
C5—N1—C6128.99 (12)N1—C5—C4113.25 (12)
C5—N1—H1N115.0 (12)N1—C6—C11121.93 (13)
C6—N1—H1N115.6 (12)N1—C6—C7121.29 (12)
O4—N2—O3121.93 (12)C11—C6—C7116.78 (13)
O4—N2—C7118.51 (12)C8—C7—C6121.60 (13)
O3—N2—C7119.56 (11)C8—C7—N2116.10 (12)
C2—C1—O1110.73 (13)C6—C7—N2122.29 (12)
C2—C1—H1124.6C9—C8—C7120.11 (13)
O1—C1—H1124.6C9—C8—H8119.9
C1—C2—C3106.62 (13)C7—C8—H8119.9
C1—C2—H2126.7C8—C9—C10119.05 (13)
C3—C2—H2126.7C8—C9—H9120.5
C4—C3—C2106.38 (13)C10—C9—H9120.5
C4—C3—H3126.8C9—C10—C11121.58 (14)
C2—C3—H3126.8C9—C10—H10119.2
C3—C4—O1110.43 (12)C11—C10—H10119.2
C3—C4—C5131.11 (13)C10—C11—C6120.86 (13)
O1—C4—C5118.38 (12)C10—C11—H11119.6
O2—C5—N1125.55 (13)C6—C11—H11119.6
C4—O1—C1—C2−0.32 (15)N1—C6—C7—C8−179.94 (12)
O1—C1—C2—C30.33 (17)C11—C6—C7—C80.84 (19)
C1—C2—C3—C4−0.21 (16)N1—C6—C7—N2−0.61 (19)
C2—C3—C4—O10.01 (15)C11—C6—C7—N2−179.83 (11)
C2—C3—C4—C5−176.78 (14)O4—N2—C7—C8−10.06 (18)
C1—O1—C4—C30.19 (15)O3—N2—C7—C8169.34 (12)
C1—O1—C4—C5177.44 (11)O4—N2—C7—C6170.57 (12)
C6—N1—C5—O22.7 (2)O3—N2—C7—C6−10.03 (19)
C6—N1—C5—C4−176.32 (12)C6—C7—C8—C9−0.4 (2)
C3—C4—C5—O2−7.1 (2)N2—C7—C8—C9−179.82 (12)
O1—C4—C5—O2176.34 (12)C7—C8—C9—C10−0.4 (2)
C3—C4—C5—N1172.03 (14)C8—C9—C10—C110.8 (2)
O1—C4—C5—N1−4.55 (17)C9—C10—C11—C6−0.3 (2)
C5—N1—C6—C11−4.7 (2)N1—C6—C11—C10−179.66 (12)
C5—N1—C6—C7176.12 (12)C7—C6—C11—C10−0.44 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.553.3857 (18)146
Symmetry code: (i) −x+1, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.553.3857 (18)146.4
Symmetry code: (i) −x+1, y+1/2, −z+3/2.
 

Acknowledgements

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

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationEtter, M. (1990). Acc. Chem. Res. 23, 120–126.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o120–o124.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationPavlović, G., Tralić-Kulenović, V. & Popović, Z. (2004). Acta Cryst. E60, o631–o633.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Page o1592
doi:10.1107/S1600536813026202
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