(E)-2-(2-Nitro-prop-1-en-yl)furan.

Crystals of the title compound, C(7)H(7)NO(3), under Mo Kα radiation sublime in less than 1h at room temperature. However, it was possible to collect data at 100K. It crystallized as the E isomer only. A double-bond conjugation in the furan ring is extended to the nitro-alkenyl group. Mol-ecular associations were realized in the crystal through N⋯π [3.545 (2) Å] inter-actions involving the furan ring and C-H⋯O hydrogen bonds.

Related literature

For general background to (nitro-alken­yl)-furan compounds, see: Yan et al. (2008 ▶); Ono N. (2006 ▶); Vallejos et al. (2005 ▶); Negrín et al. (2003 ▶); Negrín et al. (2002 ▶), Estrada et al. (1999 ▶); Agafonov et al. (1991 ▶); Gruntfest et al. (1972 ▶). For related structures, see: Valerga et al. (2009 ▶); Martínez-Bescos et al. (2008 ▶); Novoa-de-Armas et al. (1997 ▶); Pomés et al. (1995 ▶).

Experimental

Crystal data

C7H7NO3

M = 153.14

Monoclinic,

a = 7.1061 (14) Å

b = 9.4394 (19) Å

c = 10.743 (2) Å

β = 101.86 (3)°

V = 705.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.45 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.898, T max = 1.000 (expected range = 0.880–0.980)

5648 measured reflections

1620 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.07

1620 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 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/S1600536809030141/kp2230sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030141/kp2230Isup2.hkl

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

C7H7NO3	F(000) = 320
Mr = 153.14	Dx = 1.442 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2619 reflections
a = 7.1061 (14) Å	θ = 2.9–27.6°
b = 9.4394 (19) Å	µ = 0.12 mm−1
c = 10.743 (2) Å	T = 100 K
β = 101.86 (3)°	Irregular, yellow
V = 705.2 (3) Å3	0.45 × 0.30 × 0.18 mm
Z = 4

Bruker SMART APEX diffractometer	1620 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
graphite	Rint = 0.032
1700 ω scan frames, 0.3°, 10s	θmax = 27.6°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→8
Tmin = 0.898, Tmax = 1.000	k = −12→12
5648 measured reflections	l = −13→13

Refinement on F2	0 constraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.069P)2 + 0.2975P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.29 e Å−3
1620 reflections	Δρmin = −0.34 e Å−3
102 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.012 (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	0.08533 (15)	0.64923 (11)	0.35499 (10)	0.0257 (3)
O2	0.22698 (17)	0.12565 (12)	0.41245 (11)	0.0328 (3)
O3	−0.00888 (16)	0.10699 (11)	0.25033 (11)	0.0311 (3)
N1	0.09873 (17)	0.17838 (13)	0.33088 (11)	0.0227 (3)
C1	0.19682 (19)	0.55649 (15)	0.43728 (13)	0.0200 (3)
C2	0.31539 (19)	0.62992 (15)	0.53073 (13)	0.0211 (3)
H2	0.4068	0.5911	0.5993	0.025*
C3	0.2760 (2)	0.77609 (16)	0.50590 (15)	0.0272 (4)
H3	0.3360	0.8539	0.5545	0.033*
C4	0.1374 (2)	0.78256 (15)	0.40026 (16)	0.0278 (4)
H4	0.0828	0.8679	0.3620	0.033*
C5	0.18569 (19)	0.40627 (15)	0.41909 (12)	0.0194 (3)
H5	0.2709	0.3514	0.4802	0.023*
C6	0.07004 (19)	0.33308 (14)	0.32658 (12)	0.0197 (3)
C7	−0.0833 (2)	0.38425 (16)	0.22071 (14)	0.0266 (3)
H7A	−0.1245	0.4791	0.2409	0.040*
H7B	−0.1932	0.3193	0.2092	0.040*
H7C	−0.0336	0.3881	0.1422	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0287 (6)	0.0186 (5)	0.0277 (5)	0.0010 (4)	0.0008 (4)	0.0023 (4)
O2	0.0399 (7)	0.0183 (5)	0.0339 (6)	0.0058 (5)	−0.0073 (5)	0.0003 (4)
O3	0.0372 (7)	0.0217 (6)	0.0304 (6)	−0.0050 (4)	−0.0023 (5)	−0.0073 (4)
N1	0.0263 (6)	0.0186 (6)	0.0223 (6)	−0.0007 (5)	0.0028 (5)	−0.0024 (5)
C1	0.0210 (7)	0.0172 (7)	0.0222 (7)	0.0015 (5)	0.0051 (5)	0.0019 (5)
C2	0.0197 (7)	0.0216 (7)	0.0217 (7)	−0.0002 (5)	0.0038 (5)	−0.0009 (5)
C3	0.0296 (8)	0.0210 (7)	0.0324 (8)	−0.0057 (6)	0.0100 (6)	−0.0069 (6)
C4	0.0321 (8)	0.0145 (7)	0.0383 (8)	0.0012 (6)	0.0105 (6)	0.0031 (6)
C5	0.0199 (7)	0.0173 (7)	0.0206 (6)	0.0013 (5)	0.0034 (5)	0.0010 (5)
C6	0.0217 (7)	0.0164 (6)	0.0211 (7)	0.0014 (5)	0.0047 (5)	0.0005 (5)
C7	0.0292 (8)	0.0254 (7)	0.0224 (7)	0.0037 (6)	−0.0014 (6)	−0.0020 (6)

O1—C4	1.3724 (18)	C3—C4	1.342 (2)
O1—C1	1.3739 (17)	C3—H3	0.9500
O2—N1	1.2320 (16)	C4—H4	0.9500
O3—N1	1.2311 (16)	C5—C6	1.3434 (19)
N1—C6	1.4739 (18)	C5—H5	0.9500
C1—C2	1.3602 (19)	C6—C7	1.4850 (19)
C1—C5	1.431 (2)	C7—H7A	0.9800
C2—C3	1.422 (2)	C7—H7B	0.9800
C2—H2	0.9500	C7—H7C	0.9800
C4—O1—C1	106.17 (12)	C3—C4—H4	124.6
O3—N1—O2	122.73 (12)	O1—C4—H4	124.6
O3—N1—C6	117.28 (11)	C6—C5—C1	128.22 (13)
O2—N1—C6	119.99 (11)	C6—C5—H5	115.9
C2—C1—O1	109.76 (13)	C1—C5—H5	115.9
C2—C1—C5	127.88 (13)	C5—C6—N1	115.26 (12)
O1—C1—C5	122.34 (12)	C5—C6—C7	129.82 (13)
C1—C2—C3	106.73 (13)	N1—C6—C7	114.92 (12)
C1—C2—H2	126.6	C6—C7—H7A	109.5
C3—C2—H2	126.6	C6—C7—H7B	109.5
C4—C3—C2	106.53 (13)	H7A—C7—H7B	109.5
C4—C3—H3	126.7	C6—C7—H7C	109.5
C2—C3—H3	126.7	H7A—C7—H7C	109.5
C3—C4—O1	110.81 (13)	H7B—C7—H7C	109.5
C4—O1—C1—C2	−0.25 (15)	O1—C1—C5—C6	−1.4 (2)
C4—O1—C1—C5	−178.62 (12)	C1—C5—C6—N1	177.53 (12)
O1—C1—C2—C3	0.10 (15)	C1—C5—C6—C7	−2.8 (2)
C5—C1—C2—C3	178.36 (13)	O3—N1—C6—C5	177.57 (12)
C1—C2—C3—C4	0.08 (16)	O2—N1—C6—C5	−2.79 (19)
C2—C3—C4—O1	−0.24 (17)	O3—N1—C6—C7	−2.15 (18)
C1—O1—C4—C3	0.31 (16)	O2—N1—C6—C7	177.49 (12)
C2—C1—C5—C6	−179.46 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.95	2.47	3.3037 (19)	147
C5—H5···O3i	0.95	3.03	3.770 (2)	136
C4—H4···O2ii	0.95	2.65	3.2980 (19)	126
C4—H4···O3ii	0.95	2.58	3.516 (2)	170
C7—H7C···O2iii	0.98	2.70	3.310 (2)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.95	2.47	3.3037 (19)	147
C5—H5⋯O3i	0.95	3.03	3.770 (2)	136
C4—H4⋯O2ii	0.95	2.65	3.2980 (19)	126
C4—H4⋯O3ii	0.95	2.58	3.516 (2)	170
C7—H7C⋯O2iii	0.98	2.70	3.310 (2)	121

Symmetry codes: (i) ; (ii) ; (iii) .