1-Eth­oxy-2-meth­oxy-4-[2-(4-nitro­phen­yl)ethen­yl]benzene

Paul M Dinakaran; S Kalainathan; T Srinivasan; D Velmurugan

doi:10.1107/S1600536812034320

. 2012 Aug 25;68(Pt 9):o2774. doi: 10.1107/S1600536812034320

1-Ethoxy-2-methoxy-4-[2-(4-nitrophenyl)ethenyl]benzene

Paul M Dinakaran ^a, S Kalainathan ^a,^*, T Srinivasan ^b, D Velmurugan ^b

PMCID: PMC3435807 PMID: 22969653

Abstract

In the title molecule, C₁₇H₁₇NO₄, the dihedral angle between the two aromatic rings is 42.47 (7)°. The nitro group is twisted by 7.44 (11)° out of the plane of the ring to which it is attached. The methoxy and ethoxy group O atoms deviate significantly from the phenyl ring [by 0.0108 (11) and 0.0449 (11) Å, respectively]. The crystal structure is stabilized by C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Tam et al. (1989 ▶). For hybridization, see: Beddoes et al. (1986 ▶)

Experimental

Crystal data

C₁₇H₁₇NO₄
M _r = 299.32
Monoclinic,
a = 8.5209 (4) Å
b = 7.5959 (4) Å
c = 23.7877 (13) Å
β = 99.611 (3)°
V = 1518.02 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
14265 measured reflections
3789 independent reflections
2831 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.138
S = 1.04
3789 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034320/bt5986sup1.cif

e-68-o2774-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034320/bt5986Isup2.hkl

e-68-o2774-Isup2.hkl^{(182KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034320/bt5986Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cg2	0.97	2.96	3.281 (2)	145

Open in a new tab

Acknowledgments

TS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for data collection and TS thanks DST for the Inspire fellowship. PMD and SK thank SERC–DST for providing financial support and VIT University management for their constant encouragement.

supplementary crystallographic information

Comment

The dihedral angle between nitro substituted phenyl ring (C1-C6) & oxygen substituted benzene ring (C9-C14) is 42.47 (7)°. The sum of bond angles around N1 (359.59°) is in accordance with sp₂ hybridization (Beddoes et al., 1986). The methoxy and ethoxy group O3 and O4 atoms are significantly deviated from the phenyl ring (C9–C13) with the values of -0.0108 (11) Å and -0.0449 (11) Å, respectively.

A weak intermolecular C—H···π interaction involving the C17–H17A group and the C9–C14 benzene ring (centroid Cg2) of the molecule at (2-x,-y,-z) is observed [H17A···Cg2 = 2.96 Å, C17···Cg2 = 3.781 (2) Å and C17-H17A···Cg2 = 145°].

Experimental

4-Ethoxy 3-Methoxy 4-Nitrostilbene (4E3MONS) is a derivative material of stilebene.The material (4E3MONS) was synthesized by Witting reaction method. The material was prepared from the 4-ethoxy 3-methoxy benzaldehyde and diethyl p-nitrobenzyl phosphonate in the presence of sodium ethoxide catalyst. The steps involved during the chemical reactions are as follows: the calculated amount of diethyl p-nitrobenzyl phosphonate (0.01 mol %, 2.2304ml) and 4-ethoxy 3-methoxy benzaldehyde (0.01 mol, 1.802 ml %) were added in the ethanol solution (35 ml). After the reaction process, the sodium ethoxide,which plays a role of catalyst, was added immediately the colour of the solution became red. Then the mixture was stirred for 12 hrs at ice cold temperature in ultracryostat which has stirrer rotation facility. After the stirring process completed, the orange colour 4E3MONS material was collected from the mixture by removing the ethanol (Tam et al., 1989). Then the 4E3MONS was purified by a successive recrystallization process.