Crystal structure of (E)-2-({[2-(1,3-dioxan-2-yl)phen­yl]imino}­meth­yl)phenol

Zhengyi Li; Song Shi; Kun Zhou; Liang Chen; Xiaoqiang Sun

doi:10.1107/S2056989015008051

. 2015 Apr 30;71(Pt 5):o357–o358. doi: 10.1107/S2056989015008051

Crystal structure of (E)-2-({[2-(1,3-dioxan-2-yl)phenyl]imino}methyl)phenol

Zhengyi Li ^a, Song Shi ^a, Kun Zhou ^a, Liang Chen ^a, Xiaoqiang Sun ^a,^*

PMCID: PMC4420126 PMID: 25995947

Abstract

The title compound, C₁₇H₁₇NO₃, prepared by the condensation reaction of 2-(1,3-dioxan-2-yl)aniline and salicylaldehyde, has an E conformation about the C=N bond. The six-membered O-heterocycle adopts a chair conformation, with the bond to the aromatic ring located at its equatorial position. The dihedral angle between the aromatic rings is 36.54 (9)°. There is an intramolecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains along the a-axis direction. Within the chains, there are C—H⋯π interactions involving adjacent molecules.

Keywords: crystal structure, acetal, Schiff base, intramolecular hydrogen bonding, N—H⋯O hydrogen bonds

Related literature

For general background to acetals, see: Cismaş et al. (2005 ▸); Sun et al. (2010 ▸). For Schiff bases of salicylaldehyde having important applications in biological and pharmacological chemistry, see: Gupta & Sutar (2008 ▸); Jiménez-Sánchez et al. (2013 ▸). For further background to related Schiff base ligands and their various properties, see: Arod et al. (2005 ▸); Chatziefthimiou et al. (2006 ▸). graphic file with name e-71-0o357-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₇NO₃
M _r = 283.32
Orthorhombic,
a = 8.4873 (18) Å
b = 10.821 (2) Å
c = 16.232 (3) Å
V = 1490.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.978, T _max = 0.981
9005 measured reflections
3123 independent reflections
2494 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.097
S = 1.00
3123 reflections
190 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); 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 datablock(s) I, Global. DOI: 10.1107/S2056989015008051/su5122sup1.cif

e-71-0o357-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008051/su5122Isup2.hkl

e-71-0o357-Isup2.hkl^{(153.3KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015008051/su5122Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989015008051/su5122fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular O—H⋯N hydrogen bond is shown as a dashed line (see Table 1 for details).

Click here for additional data file.^{(1.2MB, tif)}

c . DOI: 10.1107/S2056989015008051/su5122fig2.tif

A partial view of the crystal packing of the title compound, view along the c axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1061272

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg1 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
O1H1N1	0.85	1.90	2.632(2)	144
C7H7O2ⁱ	0.93	2.48	3.364(2)	160
C15H15A Cg1ⁱⁱ	0.97	2.77	3.694(3)	160

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

Acknowledgments

We gratefully acknowledge financial support from the NSFC (No. 21002009), the Scientific and Technological Project of Jiangsu Province (BY2014037–01), the Major Program for Natural Science Research of Jiangsu Colleges and Universities (12KJA150002 and 14KJA150002), and the Qing Lan Project of Jiangsu Province.

supplementary crystallographic information

S1. Comment

Schiff bases of salicylaldehyde have important applications in biological chemistry and pharmacological chemistry (Gupta et al., 2008; Sánchez et al., 2013). In addition, Schiff bases of salicylaldehyde has good optical properties with the ability of distinctive ultraviolet absorption (Chatziefthimiou et al., 2006). Herein (E)-2-{[2-(1,3-dioxan-2-yl) phenyl) imino]methyl} phenol was prepared by the condensation reaction of 2-(1,3-dioxan-2-yl) aniline and salicylaldehyde, and the structure was confirmed by X-ray diffraction analysis.

In the molecular structure of the title compound, Fig. 1, the two aromatic rings (C1—C6 and C8—C13) are linked by the double bond C7═N1, with the dihedral angle between the two rings being 36.54 (9) °. The C7═N1 bond is coplanar with the benzene ring (C1—C6), and atom N1 forms an intramolecular hydrogen bond, O1—H1···N1, with the hydroxyl group on ring (C1—C6) [Fig. 1 and Table 1]. The six-membered O-heterocycle adopts a chair conformation with the (C8—C13) ring located at its equatorial position.

In the crystal, molecules are linked by C—H···O hydrogen bonds forming chain along the a axis. Within the chains there are C—H···π interactions involving adjacent molecules (Table 1 and Fig. 2).

S2. Experimental

A mixture of 2-(1,3-dioxan-2-yl) aniline (1.8 g, 10 mmol) and salicylaldehyde (1.32 g, 11 mmol) in 20 ml methanol, stirred for 20 h at room temperature. After the reaction had finished, the solution was left overnight at at 273 K, and yellow block-like crystals were obtained on slow evaporation of the solvent (yield: 82%; m.p.: 321 K).

S3. Refinement

The OH and C-bound H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms: O—H = 0.85 Å, C—H = 0.93-0.98 Å, with U_iso(H) = 1.5U_eq(O) and 1.2U_eq(C) for other H atoms.