(E)-N-(2,4-Dimeth­oxy­benzyl­idene)-4-ethoxyaniline

Karla Fejfarová; Aliakbar Dehno Khalaji; Michal Dušek

doi:10.1107/S1600536810041759

. 2010 Oct 20;66(Pt 11):o2874. doi: 10.1107/S1600536810041759

(E)-N-(2,4-Dimethoxybenzylidene)-4-ethoxyaniline

Karla Fejfarová ^a,^*, Aliakbar Dehno Khalaji ^b, Michal Dušek ^c

PMCID: PMC3008983 PMID: 21589056

Abstract

In the title compound, C₁₇H₁₉NO₃, the molecule has an E configuration with respect to the C=N bond and the dihedral angle between the aromatic rings is 56.07 (5)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur. The dimers are linked by weak C—H⋯π interactions, forming a three-dimensional network.

Related literature

For related structures and background references, see: Khalaji et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₉NO₃
M _r = 285.3
Monoclinic,
a = 8.4536 (1) Å
b = 9.6531 (2) Å
c = 18.0561 (3) Å
β = 90.9091 (10)°
V = 1473.25 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 120 K
0.50 × 0.12 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶), T _min = 0.714, T _max = 1.000
18522 measured reflections
2543 independent reflections
2259 reflections with I > 3σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.098
S = 1.98
2543 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041759/hb5685sup1.cif

e-66-o2874-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041759/hb5685Isup2.hkl

e-66-o2874-Isup2.hkl^{(122.6KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8c⋯O2ⁱ	0.96	2.52	3.3745 (13)	148
C5—H5⋯Cg2ⁱⁱ	0.96	2.88	3.7529 (11)	152
C14—H14⋯Cg1ⁱⁱⁱ	0.96	2.76	3.6019 (11)	147

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

Acknowledgments

We acknowledge Golestan University (GU), the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

supplementary crystallographic information

Comment

As part of our ongoing studies of Schiff bases (Khalaji et al., 2010a and 2010b) we now report the synthesis and crystal structure of the title compound, (I).

The title molecule with the atomic numbering scheme is depicted in Fig. 1. The C7—N1 and C10—N1 bond lengths of 1.2795 (13), 1.4171 (13) Å, respectively, conform to the value for a double and single bonds, respectively, and they are similar to the corresponding bond lengths in another Schiff-base compounds (Khalaji et al., 2010a and 2010b).

The torsion angle of the title compound, C10—N1—C7—C1 - 175.18 (9)°, indicates virtually planar E-configuration with respect to the imine C–N bond. Both methoxy groups are nearly coplanar with the C1—C6 ring, as indicated by torsion angles C3—C4—O2—C9 and C1—C2—O1—C8 of 178.16 (9)°, -175.74 (9)°, respectively. The ethoxy group is nearly coplanar with the C10—C15 ring, with the dihedral angle between the ring plane and plane defined by atoms O3, C16 and C17 of 6.28 (9)°.

In the crystal, molecules are connected by weak C—H···O interactions into dimers, which are further linked by C—H···π interactions into a three-dimensional network.