1,2-Dimeth­oxy-3-[(E)-2-nitro­ethen­yl]benzene

Ren, Y.; Zhu, R.

doi:10.1107/S1600536810030539

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2249

https://doi.org/10.1107/S1600536810030539

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1,2-Dimethoxy-3-[(E)-2-nitroethenyl]benzene

Yuehong Ren ^a and Ruitao Zhu ^a ^*

^aDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: ruitaozhu@126.com

(Received 23 July 2010; accepted 30 July 2010; online 11 August 2010)

The title compound, C₁₀H₁₁NO₄, was synthesized via condensation of 2,3-dimethoxybenzaldehyde with nitromethane 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 nitroalkenyl 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_r = 209.20
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.058
wR(F²) = 0.226
S = 1.14
1798 reflections
139 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030539/lh5097Isup2.hkl

checkCIF report

Comment top

Nitroalkenes are good substrates for Michael addition reactions because of the stronger electron withdrawing property of the nitro group (Ranu et al., 2005). In addition, the nitro group can provide a good nitrogen source for the synthesis of many useful organic molecules (Ballini et al., 2005). Our group has focused on new organic transformations obtained by nitroalkenes as substrates. In this paper, we report the structure of the title compound. The crystal structure of the title compound is shown in Fig. 1. 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 nitroalkenyl group is 23.90 (6)°. The bond lengths and angles in the tilte compound can be compared to those in (E)-β-nitrostyrene (Pedireddi et al., 1992).

Related literature top

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 top

The title compound was prepared according to a method reported in the literature (Wang et al. (2002): A mixture of 0.83 g (5 mmol) 2,3-dimethoxy-benzaldehyde, 1.53 g (25 mmol) nitromethane and 0.35 g potassium carbonate was finely ground by agate mortar and pestle and was mixed with 5 g aluminium oxide (150mesh). The mixture was then put in a 25 ml beaker and introduced into a microwave oven. Microwave irradiation was carried out for 5 min. The mixture was cooled to ambient temperature, then water and nitromethane were removed by reduced pressure. The residue was purified by silica gel chromatography (pertroleum ether/ethyl acetate/dichloromethane. 1:1:0.3) to give the product (yield 75%). Crystals suitable for X-ray analysis were obtained after one week by slow evaporation from an ethyl alcohol solution of the title compound.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of the title compound, displacement ellipsoids are drawn at the 30% probability level.

1,2-Dimethoxy-3-[(E)-2-nitroethenyl]benzene top

Crystal data top

C₁₀H₁₁NO₄	F(000) = 440
M_r = 209.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1507P)²] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
1798 reflections	Δρ_max = 0.41 e Å⁻³
139 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₁₁NO₄	V = 1030.41 (18) Å³
M_r = 209.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3558 (7) Å	µ = 0.11 mm⁻¹
b = 13.5897 (11) Å	T = 296 K
c = 14.2646 (12) Å	0.38 × 0.35 × 0.34 mm
β = 97.038 (1)°

Data collection top

Bruker APEXII CCD diffractometer	1798 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1351 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.965	R_int = 0.035
4852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.226	H-atom parameters constrained
S = 1.14	Δρ_max = 0.41 e Å⁻³
1798 reflections	Δρ_min = −0.41 e Å⁻³
139 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁NO₄
M_r	209.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.3558 (7), 13.5897 (11), 14.2646 (12)
β (°)	97.038 (1)
V (Å³)	1030.41 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.35 × 0.34

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	4852, 1798, 1351
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.226, 1.14
No. of reflections	1798
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.41

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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