1,2-Dimeth-oxy-3-[(E)-2-nitro-ethen-yl]benzene.

The title compound, C(10)H(11)NO(4), was synthesized via condensation of 2,3-dimeth-oxy-benzaldehyde with nitro-methane using microwave irradiation without solvent. The H atoms of the -CH=CH- group are in a trans configuration. The dihedral angle between the mean planes of the benzene ring and the nitro-alkenyl group is 23.90 (6)°.

Related literature

For the use of nitro­alkenes in organic synthesis, see: Ranu & Banerjee (2005 ▶); Ballini et al. (2005 ▶). For a related structure, see: Pedireddi et al. (1992 ▶). For the synthetic procedure, see: Wang & Wang (2002 ▶).

Experimental

Crystal data

C10H11NO4

M = 209.20

Monoclinic,

a = 5.3558 (7) Å

b = 13.5897 (11) Å

c = 14.2646 (12) Å

β = 97.038 (1)°

V = 1030.41 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.38 × 0.35 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.965

4852 measured reflections

1798 independent reflections

1351 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.226

S = 1.14

1798 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030539/lh5097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030539/lh5097Isup2.hkl

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

C10H11NO4	F(000) = 440
Mr = 209.20	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1678 reflections
a = 5.3558 (7) Å	θ = 3.0–25.5°
b = 13.5897 (11) Å	µ = 0.11 mm−1
c = 14.2646 (12) Å	T = 296 K
β = 97.038 (1)°	Flake, colorless
V = 1030.41 (18) Å3	0.38 × 0.35 × 0.34 mm
Z = 4

Bruker APEXII CCD diffractometer	1798 independent reflections
Radiation source: fine-focus sealed tube	1351 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.961, Tmax = 0.965	k = −16→15
4852 measured reflections	l = −15→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.226	w = 1/[σ2(Fo2) + (0.1507P)2] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
1798 reflections	Δρmax = 0.41 e Å−3
139 parameters	Δρmin = −0.41 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.17 (3)

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 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
N1	0.8816 (4)	0.34090 (16)	0.43863 (15)	0.0521 (7)
O1	1.0954 (4)	0.35541 (16)	0.47743 (16)	0.0740 (7)
O2	0.7912 (4)	0.25907 (15)	0.42869 (17)	0.0818 (8)
O3	0.1183 (3)	0.38811 (12)	0.21248 (12)	0.0532 (6)
O4	−0.2003 (3)	0.53204 (13)	0.14689 (13)	0.0581 (6)
C1	0.7376 (5)	0.4265 (2)	0.40583 (19)	0.0544 (7)
H1A	0.7990	0.4887	0.4234	0.065*
C2	0.5216 (5)	0.4187 (2)	0.35173 (16)	0.0503 (7)
H2	0.4684	0.3556	0.3335	0.060*
C3	0.3580 (4)	0.50020 (18)	0.31776 (16)	0.0454 (7)
C4	0.1580 (4)	0.48261 (15)	0.24744 (16)	0.0439 (7)
C5	−0.0092 (4)	0.55801 (18)	0.21569 (17)	0.0470 (7)
C6	0.0260 (5)	0.65146 (18)	0.2532 (2)	0.0532 (7)
H6	−0.0844	0.7019	0.2324	0.064*
C7	0.2273 (5)	0.6697 (2)	0.3224 (2)	0.0583 (8)
H7	0.2515	0.7328	0.3470	0.070*
C8	0.3908 (5)	0.5959 (2)	0.35469 (18)	0.0546 (7)
H8	0.5237	0.6092	0.4012	0.066*
C9	0.2010 (7)	0.3753 (2)	0.1216 (2)	0.0716 (9)
H9A	0.1121	0.4202	0.0774	0.107*
H9B	0.1682	0.3090	0.1005	0.107*
H9C	0.3783	0.3882	0.1259	0.107*
C10	−0.3741 (5)	0.6077 (2)	0.11368 (19)	0.0605 (8)
H10A	−0.4538	0.6327	0.1655	0.091*
H10B	−0.4994	0.5811	0.0666	0.091*
H10C	−0.2858	0.6600	0.0867	0.091*

	U11	U22	U33	U12	U13	U23
N1	0.0511 (13)	0.0521 (13)	0.0517 (13)	0.0009 (9)	0.0004 (10)	0.0000 (9)
O1	0.0514 (13)	0.0756 (14)	0.0899 (16)	−0.0045 (9)	−0.0114 (11)	0.0064 (11)
O2	0.0785 (14)	0.0510 (13)	0.1072 (18)	−0.0008 (11)	−0.0232 (12)	−0.0064 (11)
O3	0.0637 (12)	0.0361 (10)	0.0589 (11)	−0.0052 (7)	0.0039 (8)	−0.0025 (7)
O4	0.0527 (11)	0.0494 (12)	0.0677 (12)	0.0033 (8)	−0.0113 (9)	−0.0026 (8)
C1	0.0542 (16)	0.0471 (15)	0.0607 (15)	−0.0005 (11)	0.0027 (12)	0.0022 (12)
C2	0.0519 (15)	0.0492 (15)	0.0498 (14)	−0.0010 (11)	0.0064 (11)	−0.0013 (11)
C3	0.0460 (13)	0.0461 (14)	0.0443 (12)	0.0015 (10)	0.0064 (10)	0.0018 (10)
C4	0.0498 (13)	0.0343 (13)	0.0484 (13)	−0.0022 (9)	0.0097 (11)	0.0010 (9)
C5	0.0473 (14)	0.0442 (14)	0.0497 (13)	0.0013 (10)	0.0064 (11)	0.0017 (10)
C6	0.0563 (16)	0.0438 (15)	0.0592 (15)	0.0077 (10)	0.0061 (12)	−0.0032 (11)
C7	0.0644 (18)	0.0476 (15)	0.0614 (16)	0.0029 (12)	0.0023 (13)	−0.0131 (11)
C8	0.0543 (15)	0.0543 (16)	0.0542 (15)	−0.0005 (12)	0.0029 (11)	−0.0100 (12)
C9	0.093 (2)	0.0542 (17)	0.0689 (19)	−0.0040 (15)	0.0134 (16)	−0.0164 (14)
C10	0.0549 (16)	0.0626 (18)	0.0621 (17)	0.0057 (13)	−0.0009 (13)	0.0123 (13)

N1—O2	1.214 (3)	C4—C5	1.399 (3)
N1—O1	1.225 (3)	C5—C6	1.382 (3)
N1—C1	1.442 (3)	C6—C7	1.391 (4)
O3—C4	1.385 (3)	C6—H6	0.9300
O3—C9	1.431 (3)	C7—C8	1.374 (4)
O4—C5	1.375 (3)	C7—H7	0.9300
O4—C10	1.428 (3)	C8—H8	0.9300
C1—C2	1.314 (3)	C9—H9A	0.9600
C1—H1A	0.9300	C9—H9B	0.9600
C2—C3	1.458 (4)	C9—H9C	0.9600
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.395 (3)	C10—H10B	0.9600
C3—C8	1.406 (4)	C10—H10C	0.9600
O2—N1—O1	122.5 (2)	C5—C6—H6	120.1
O2—N1—C1	120.7 (2)	C7—C6—H6	120.1
O1—N1—C1	116.7 (2)	C8—C7—C6	120.9 (2)
C4—O3—C9	112.83 (19)	C8—C7—H7	119.5
C5—O4—C10	116.8 (2)	C6—C7—H7	119.5
C2—C1—N1	121.5 (2)	C7—C8—C3	120.3 (2)
C2—C1—H1A	119.2	C7—C8—H8	119.8
N1—C1—H1A	119.2	C3—C8—H8	119.8
C1—C2—C3	125.7 (2)	O3—C9—H9A	109.5
C1—C2—H2	117.1	O3—C9—H9B	109.5
C3—C2—H2	117.1	H9A—C9—H9B	109.5
C4—C3—C8	118.5 (2)	O3—C9—H9C	109.5
C4—C3—C2	119.1 (2)	H9A—C9—H9C	109.5
C8—C3—C2	122.4 (2)	H9B—C9—H9C	109.5
O3—C4—C3	119.2 (2)	O4—C10—H10A	109.5
O3—C4—C5	119.9 (2)	O4—C10—H10B	109.5
C3—C4—C5	120.8 (2)	H10A—C10—H10B	109.5
O4—C5—C6	124.5 (2)	O4—C10—H10C	109.5
O4—C5—C4	115.7 (2)	H10A—C10—H10C	109.5
C6—C5—C4	119.7 (2)	H10B—C10—H10C	109.5
C5—C6—C7	119.7 (2)
O2—N1—C1—C2	−10.7 (4)	C10—O4—C5—C4	179.7 (2)
O1—N1—C1—C2	170.1 (2)	O3—C4—C5—O4	−2.8 (3)
N1—C1—C2—C3	177.7 (2)	C3—C4—C5—O4	−179.41 (19)
C1—C2—C3—C4	168.5 (2)	O3—C4—C5—C6	177.7 (2)
C1—C2—C3—C8	−12.9 (4)	C3—C4—C5—C6	1.0 (4)
C9—O3—C4—C3	−103.4 (3)	O4—C5—C6—C7	−179.6 (2)
C9—O3—C4—C5	79.9 (3)	C4—C5—C6—C7	−0.1 (4)
C8—C3—C4—O3	−177.9 (2)	C5—C6—C7—C8	−0.6 (4)
C2—C3—C4—O3	0.7 (3)	C6—C7—C8—C3	0.4 (4)
C8—C3—C4—C5	−1.3 (3)	C4—C3—C8—C7	0.5 (4)
C2—C3—C4—C5	177.4 (2)	C2—C3—C8—C7	−178.1 (2)
C10—O4—C5—C6	−0.7 (4)