(E)-N-(2,3,4-Trimeth­oxy-6-methyl­benzyl­idene)aniline

Hui Zhang

doi:10.1107/S1600536808016620

. 2008 Jun 7;64(Pt 7):o1219. doi: 10.1107/S1600536808016620

(E)-N-(2,3,4-Trimethoxy-6-methylbenzylidene)aniline

Hui Zhang ^a,^*

PMCID: PMC2961677 PMID: 21202856

Abstract

In the title compound, C₁₇H₁₉NO₃, the C—C=N—C torsion angle between the benzene and phenyl rings is −177.3 (2)°, and the dihedral angle between the rings is 54.6 (2)°. The crystal structure is stabilized by intramolecular hydrogen bonds and weak π–π and C—H⋯π interactions.

Related literature

For related literature, see: Zhang et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₉NO₃
M _r = 285.33
Triclinic,
a = 8.3126 (13) Å
b = 9.9938 (17) Å
c = 10.8661 (19) Å
α = 110.102 (2)°
β = 111.995 (2)°
γ = 92.7000 (10)°
V = 769.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.50 × 0.48 × 0.47 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.959, T _max = 0.962
3966 measured reflections
2650 independent reflections
1571 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.170
S = 1.00
2650 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016620/bx2141sup1.cif

e-64-o1219-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016620/bx2141Isup2.hkl

e-64-o1219-Isup2.hkl^{(130.1KB, hkl)}

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

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

Cg2 is the centroid of the ring C12–C17.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.93	2.32	2.714 (3)	105
C8—H8C⋯O2	0.96	2.47	3.062 (5)	120
C9—H9C⋯O1	0.96	2.53	3.079 (4)	116
C10—H10C⋯Cg2ⁱ	0.96	2.98	3.894 (4)	160

Open in a new tab

Symmetry code: (i) Inline graphic .

Table 2. π–π interactions (Å, °).

Cg1 is the centroid of the ring C2–C7. The offset is defined as the distance between CgI and the perpendicular projection of CgJ on ring I.

CgI⋯CgJ	CgI⋯CgJ	Dihedral angle	Interplanar distance	Offset
Cg1⋯Cg1ⁱ	4.236 (1)		3.523 (1)	2.352

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The preparation, properties and applications of Schiff bases are important in the development of coordination chemistry. In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1. The bond lengths and angles of the title compound agree with those in the related compound 2,3,4-Trimethoxy-6-methylbenzaldehyde (Zhang et al., 2005), as representative example. The dihedral angle between the two phenyl rings is 125.4 (2)°. The crystal structure is stabilized by an intramolecular hydrogen bonding and weak π–π and C—H···π interactions ( Table 1 and Table 2).

Experimental

To a solution of p-toluidine (0.535 g, 5 mmol) and potassium acetate (0.980 g, 10 mmol) in distilled water (10 ml), 2,3,4-Trimethoxy-6-methylbenzaldehyde (1.04 g, 5 mmol) in ethylalcohol (20 ml) was added drop by drop, the solution was stirred for 1 h at reflux temperature. The precipitate was filtered and dried. 10 mg of (I) was dissolved in 15 ml ethanol and the solution was allowed to evaporate at room temperature. Straw yellow single crystals of the title compound were formed after one week.