(E)-2-(2-Nitro-ethen-yl)furan.

The title compound, C(6)H(5)NO(3), was synthesized via condensation of furfural with nitro-methane in the presence of isobutyl-amine. The compound crystallizes exclusively as the E isomer. The angle between the mean planes of the furan ring and the nitro-alkenyl group is 1.3 (2)°.

Related literature

For general background, see: Wang et al. (2009 ▶); An et al. (2007 ▶); Rastogi et al. (2006 ▶); Rao et al. (2005 ▶); Negrín et al. (2002 ▶, 2003 ▶); Vallejosa et al. (2005 ▶). For related structures, see: Martínez-Bescos et al. (2008 ▶); Novoa-de-Armas et al. (1997 ▶); Pomes et al. (1995 ▶).

Experimental

Crystal data

C6H5NO3

M = 139.11

Monoclinic,

a = 9.0374 (18) Å

b = 5.2012 (10) Å

c = 13.027 (3) Å

β = 97.58 (3)°

V = 607.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.47 × 0.17 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.916, T max = 0.980

4852 measured reflections

1387 independent reflections

1317 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.06

1387 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902861X/fj2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902861X/fj2237Isup2.hkl

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

C6H5NO3	F(000) = 288
Mr = 139.11	Dx = 1.522 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2396 reflections
a = 9.0374 (18) Å	θ = 2.6–27.5°
b = 5.2012 (10) Å	µ = 0.13 mm−1
c = 13.027 (3) Å	T = 100 K
β = 97.58 (3)°	Prism, yellow
V = 607.0 (2) Å3	0.47 × 0.17 × 0.14 mm
Z = 4

Bruker SMART APEX diffractometer	1387 independent reflections
Radiation source: fine-focus sealed tube	1317 reflections with I > 2σ(I)
graphite	Rint = 0.023
1700 ω scan frames (0.3°, 10)	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.916, Tmax = 0.980	k = −6→6
4852 measured reflections	l = −16→12

Refinement on F2	0 restraints
Least-squares matrix: full	0 constraints
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.266P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1387 reflections	Δρmax = 0.25 e Å−3
91 parameters	Δρmin = −0.28 e Å−3

Experimental. Refinement of F2 against unique set of 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 > 2sigma(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.

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

Refinement. Refinement of F2 against unique set of 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	0.67495 (10)	0.19614 (17)	0.08110 (7)	0.0206 (2)
O2	0.15283 (11)	0.49888 (19)	0.10417 (8)	0.0290 (3)
O3	0.16242 (10)	0.13012 (19)	0.18291 (7)	0.0254 (3)
N1	0.21943 (12)	0.3007 (2)	0.13567 (8)	0.0205 (3)
C1	0.59854 (14)	0.0119 (2)	0.12894 (9)	0.0182 (3)
C2	0.68866 (14)	−0.1941 (2)	0.15531 (9)	0.0202 (3)
H2	0.6627	−0.3465	0.1890	0.024*
C3	0.82904 (14)	−0.1370 (3)	0.12270 (10)	0.0221 (3)
H3	0.9152	−0.2435	0.1300	0.027*
C4	0.81535 (14)	0.0996 (3)	0.07909 (10)	0.0227 (3)
H4	0.8930	0.1870	0.0508	0.027*
C5	0.44755 (13)	0.0618 (2)	0.14455 (9)	0.0185 (3)
H5	0.3974	−0.0667	0.1787	0.022*
C6	0.37162 (14)	0.2755 (3)	0.11477 (10)	0.0197 (3)
H6	0.4172	0.4090	0.0803	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0179 (4)	0.0200 (5)	0.0243 (5)	0.0009 (3)	0.0046 (3)	0.0019 (3)
O2	0.0269 (5)	0.0301 (5)	0.0303 (5)	0.0112 (4)	0.0053 (4)	0.0047 (4)
O3	0.0206 (5)	0.0269 (5)	0.0299 (5)	−0.0014 (4)	0.0074 (4)	0.0019 (4)
N1	0.0189 (5)	0.0244 (6)	0.0182 (5)	0.0026 (4)	0.0023 (4)	−0.0017 (4)
C1	0.0199 (6)	0.0185 (6)	0.0163 (6)	−0.0013 (4)	0.0027 (4)	−0.0017 (4)
C2	0.0221 (6)	0.0199 (6)	0.0186 (6)	0.0006 (5)	0.0019 (5)	−0.0010 (5)
C3	0.0201 (6)	0.0256 (6)	0.0204 (6)	0.0042 (5)	0.0016 (5)	−0.0025 (5)
C4	0.0164 (6)	0.0279 (7)	0.0242 (6)	0.0007 (5)	0.0040 (5)	−0.0011 (5)
C5	0.0185 (6)	0.0212 (6)	0.0159 (6)	−0.0021 (5)	0.0028 (4)	−0.0023 (4)
C6	0.0170 (6)	0.0236 (6)	0.0194 (6)	0.0002 (5)	0.0052 (4)	−0.0013 (5)

O1—C4	1.3680 (15)	C2—H2	0.9500
O1—C1	1.3772 (15)	C3—C4	1.3544 (19)
O2—N1	1.2361 (14)	C3—H3	0.9500
O3—N1	1.2309 (15)	C4—H4	0.9500
N1—C6	1.4428 (16)	C5—C6	1.3366 (18)
C1—C2	1.3623 (17)	C5—H5	0.9500
C1—C5	1.4296 (17)	C6—H6	0.9500
C2—C3	1.4214 (18)
C4—O1—C1	105.97 (10)	C4—C3—H3	126.9
O3—N1—O2	123.33 (11)	C2—C3—H3	126.9
O3—N1—C6	120.08 (11)	C3—C4—O1	111.04 (12)
O2—N1—C6	116.59 (11)	C3—C4—H4	124.5
C2—C1—O1	110.03 (11)	O1—C4—H4	124.5
C2—C1—C5	131.07 (12)	C6—C5—C1	124.94 (12)
O1—C1—C5	118.89 (11)	C6—C5—H5	117.5
C1—C2—C3	106.73 (11)	C1—C5—H5	117.5
C1—C2—H2	126.6	C5—C6—N1	119.11 (12)
C3—C2—H2	126.6	C5—C6—H6	120.4
C4—C3—C2	106.23 (11)	N1—C6—H6	120.4
C4—O1—C1—C2	−0.39 (13)	C1—O1—C4—C3	0.54 (14)
C4—O1—C1—C5	178.58 (10)	C2—C1—C5—C6	179.68 (13)
O1—C1—C2—C3	0.12 (14)	O1—C1—C5—C6	0.96 (18)
C5—C1—C2—C3	−178.69 (12)	C1—C5—C6—N1	−179.91 (11)
C1—C2—C3—C4	0.21 (14)	O3—N1—C6—C5	2.03 (17)
C2—C3—C4—O1	−0.47 (14)	O2—N1—C6—C5	−178.15 (11)