N-(2-Nitro-phen-yl)furan-2-carboxamide.

In the title furan-carboxamide 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, mol-ecules are linked by weak C-H⋯O inter-actions, 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 = 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

Δρmax = 0.21 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813026202/gg2129sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026202/gg2129Isup3.cml

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

C11H8N2O4	F(000) = 480
Mr = 232.19	Dx = 1.519 Mg m−3
Monoclinic, P21/c	Melting point: 388(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0380 (5) Å	Cell parameters from 4090 reflections
b = 12.8072 (9) Å	θ = 3.2–28.8°
c = 11.3701 (9) Å	µ = 0.12 mm−1
β = 97.819 (6)°	T = 123 K
V = 1015.34 (13) Å3	Block, colourless
Z = 4	0.35 × 0.33 × 0.25 mm

Oxford Diffraction Xcalibur E diffractometer	1859 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 28.8°, θmin = 3.2°
ω scans	h = −9→8
4090 measured reflections	k = −16→17
2649 independent reflections	l = −7→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H 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 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.33408 (13)	0.25426 (7)	0.47056 (8)	0.0224 (2)
O2	0.39374 (15)	0.05694 (8)	0.69240 (9)	0.0285 (3)
O3	0.10004 (16)	0.07661 (8)	0.27664 (9)	0.0296 (3)
O4	0.02689 (18)	−0.05720 (9)	0.16525 (9)	0.0374 (3)
N1	0.27083 (16)	0.05097 (9)	0.49375 (10)	0.0188 (3)
N2	0.08218 (17)	−0.01884 (10)	0.26244 (10)	0.0228 (3)
C1	0.3632 (2)	0.35951 (11)	0.48419 (14)	0.0263 (3)
H1	0.3458	0.4089	0.4213	0.032*
C2	0.4197 (2)	0.38338 (12)	0.59859 (14)	0.0270 (3)
H2	0.4482	0.4510	0.6306	0.032*
C3	0.4287 (2)	0.28777 (12)	0.66254 (13)	0.0244 (3)
H3	0.4647	0.2788	0.7455	0.029*
C4	0.37595 (18)	0.21213 (11)	0.58195 (12)	0.0190 (3)
C5	0.34973 (18)	0.09956 (11)	0.59629 (11)	0.0190 (3)
C6	0.21685 (18)	−0.05325 (11)	0.47586 (12)	0.0177 (3)
C7	0.12627 (18)	−0.08875 (11)	0.36456 (12)	0.0191 (3)
C8	0.07181 (19)	−0.19269 (12)	0.34607 (13)	0.0231 (3)
H8	0.0103	−0.2145	0.2705	0.028*
C9	0.1070 (2)	−0.26394 (11)	0.43720 (13)	0.0252 (3)
H9	0.0696	−0.3348	0.4252	0.030*
C10	0.1977 (2)	−0.23083 (11)	0.54624 (13)	0.0239 (3)
H10	0.2235	−0.2800	0.6089	0.029*
C11	0.25161 (19)	−0.12788 (11)	0.56631 (12)	0.0209 (3)
H11	0.3131	−0.1075	0.6424	0.025*
H1N	0.239 (2)	0.0920 (14)	0.4345 (16)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0275 (5)	0.0196 (5)	0.0194 (5)	−0.0012 (4)	0.0004 (4)	0.0016 (4)
O2	0.0413 (6)	0.0249 (6)	0.0174 (5)	−0.0017 (5)	−0.0024 (4)	0.0014 (4)
O3	0.0428 (7)	0.0219 (6)	0.0223 (6)	0.0006 (5)	−0.0018 (4)	0.0005 (4)
O4	0.0554 (8)	0.0350 (7)	0.0188 (6)	−0.0021 (6)	−0.0061 (5)	−0.0061 (5)
N1	0.0222 (6)	0.0177 (6)	0.0161 (6)	0.0003 (5)	0.0007 (4)	0.0012 (5)
N2	0.0235 (6)	0.0260 (7)	0.0185 (6)	0.0012 (5)	0.0017 (5)	−0.0020 (5)
C1	0.0279 (8)	0.0188 (7)	0.0318 (8)	−0.0014 (6)	0.0021 (6)	0.0032 (6)
C2	0.0291 (8)	0.0211 (7)	0.0312 (8)	−0.0040 (6)	0.0048 (6)	−0.0044 (6)
C3	0.0249 (7)	0.0257 (8)	0.0225 (7)	−0.0044 (6)	0.0033 (5)	−0.0042 (6)
C4	0.0174 (6)	0.0225 (7)	0.0171 (7)	0.0002 (5)	0.0022 (5)	0.0008 (5)
C5	0.0178 (6)	0.0217 (7)	0.0176 (7)	0.0000 (6)	0.0027 (5)	−0.0007 (6)
C6	0.0144 (6)	0.0193 (7)	0.0200 (7)	0.0006 (5)	0.0047 (5)	−0.0007 (5)
C7	0.0170 (6)	0.0216 (7)	0.0191 (7)	0.0011 (5)	0.0039 (5)	−0.0011 (6)
C8	0.0196 (7)	0.0268 (8)	0.0237 (7)	−0.0025 (6)	0.0060 (5)	−0.0070 (6)
C9	0.0249 (7)	0.0199 (7)	0.0322 (8)	−0.0046 (6)	0.0096 (6)	−0.0034 (6)
C10	0.0245 (7)	0.0211 (7)	0.0274 (8)	0.0000 (6)	0.0079 (6)	0.0042 (6)
C11	0.0203 (7)	0.0227 (7)	0.0196 (7)	−0.0001 (6)	0.0022 (5)	−0.0004 (6)

O1—C1	1.3690 (17)	C3—C4	1.3503 (19)
O1—C4	1.3713 (16)	C3—H3	0.9500
O2—C5	1.2231 (16)	C4—C5	1.4653 (19)
O3—N2	1.2371 (16)	C6—C11	1.4009 (19)
O4—N2	1.2235 (15)	C6—C7	1.4125 (18)
N1—C5	1.3706 (17)	C7—C8	1.393 (2)
N1—C6	1.3952 (17)	C8—C9	1.378 (2)
N1—H1N	0.860 (18)	C8—H8	0.9500
N2—C7	1.4656 (18)	C9—C10	1.381 (2)
C1—C2	1.343 (2)	C9—H9	0.9500
C1—H1	0.9500	C10—C11	1.3824 (19)
C2—C3	1.421 (2)	C10—H10	0.9500
C2—H2	0.9500	C11—H11	0.9500
C1—O1—C4	105.83 (11)	O2—C5—C4	121.20 (13)
C5—N1—C6	128.99 (12)	N1—C5—C4	113.25 (12)
C5—N1—H1N	115.0 (12)	N1—C6—C11	121.93 (13)
C6—N1—H1N	115.6 (12)	N1—C6—C7	121.29 (12)
O4—N2—O3	121.93 (12)	C11—C6—C7	116.78 (13)
O4—N2—C7	118.51 (12)	C8—C7—C6	121.60 (13)
O3—N2—C7	119.56 (11)	C8—C7—N2	116.10 (12)
C2—C1—O1	110.73 (13)	C6—C7—N2	122.29 (12)
C2—C1—H1	124.6	C9—C8—C7	120.11 (13)
O1—C1—H1	124.6	C9—C8—H8	119.9
C1—C2—C3	106.62 (13)	C7—C8—H8	119.9
C1—C2—H2	126.7	C8—C9—C10	119.05 (13)
C3—C2—H2	126.7	C8—C9—H9	120.5
C4—C3—C2	106.38 (13)	C10—C9—H9	120.5
C4—C3—H3	126.8	C9—C10—C11	121.58 (14)
C2—C3—H3	126.8	C9—C10—H10	119.2
C3—C4—O1	110.43 (12)	C11—C10—H10	119.2
C3—C4—C5	131.11 (13)	C10—C11—C6	120.86 (13)
O1—C4—C5	118.38 (12)	C10—C11—H11	119.6
O2—C5—N1	125.55 (13)	C6—C11—H11	119.6
C4—O1—C1—C2	−0.32 (15)	N1—C6—C7—C8	−179.94 (12)
O1—C1—C2—C3	0.33 (17)	C11—C6—C7—C8	0.84 (19)
C1—C2—C3—C4	−0.21 (16)	N1—C6—C7—N2	−0.61 (19)
C2—C3—C4—O1	0.01 (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—C3	0.19 (15)	O3—N2—C7—C8	169.34 (12)
C1—O1—C4—C5	177.44 (11)	O4—N2—C7—C6	170.57 (12)
C6—N1—C5—O2	2.7 (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—O2	176.34 (12)	C7—C8—C9—C10	−0.4 (2)
C3—C4—C5—N1	172.03 (14)	C8—C9—C10—C11	0.8 (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—C7	176.12 (12)	C7—C6—C11—C10	−0.44 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.55	3.3857 (18)	146

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) .