A new polymorph of 1-({[1,3-dihy­droxy-2-(hy­droxy­meth­yl)propan-2-yl]iminio}meth­yl)naphthalen-2-olate

Ailing Guo; Shurong Zhang; Kun Wang; Ruitao Zhu

doi:10.1107/S205698901501539X

. 2015 Aug 26;71(Pt 9):o686–o687. doi: 10.1107/S205698901501539X

A new polymorph of 1-({[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminio}methyl)naphthalen-2-olate

Ailing Guo ^a, Shurong Zhang ^a, Kun Wang ^a, Ruitao Zhu ^b,^*

PMCID: PMC4555412 PMID: 26396905

Abstract

The title compound, C₁₅H₁₇NO₄, containing two molecules in the asymmetric unit is a polymorph of the crystal structure published by Martínez et al. [(2011). Eur. J. Org. Chem. pp. 3137-3145] which at 120 K is monoclinic with one molecule in the asymmetric unit. Both molecules in the title compound are in the trans form. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds connect molecules, forming a two-dimensional network parallel to (001).

Keywords: Schiff base, 2-hydroxy-1-naphthaldehyde, O—H⋯O hydrogen bonding, N—H⋯O hydrogen bonding, crystal structure

Related literature

For applications of Schiff bases, see: Weber et al. (2007 ▸); Chen et al. (2008 ▸); May et al.(2004 ▸). For background to the potential use of the title compound, see: Dong et al. (2014 ▸); Liu et al. (2014 ▸). For the structures of related Schiff bases derived from 2-hydroxynapthaldehyde, see: Wang et al. (2011 ▸); Kennedy et al. (2013 ▸); Abu-Dief et al. (2015 ▸). For the first polymorph, see: Martínez et al. (2011 ▸). graphic file with name e-71-0o686-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₇NO₄
M _r = 275.30
Monoclinic,
a = 9.3540 (8) Å
b = 10.0280 (9) Å
c = 29.036 (3) Å
β = 91.559 (1)°
V = 2722.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.49 × 0.45 × 0.44 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▸) T _min = 0.954, T _max = 0.958
13224 measured reflections
4775 independent reflections
2778 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.137
S = 1.05
4775 reflections
368 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); 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 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901501539X/lh5776sup1.cif

e-71-0o686-sup1.cif^{(26.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501539X/lh5776Isup2.hkl

e-71-0o686-Isup2.hkl^{(233.9KB, hkl)}

Click here for additional data file.^{(53KB, tif)}

. DOI: 10.1107/S205698901501539X/lh5776fig1.tif

The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S205698901501539X/lh5776fig2.tif

Part of the crystal structure with the hydrogen bonds drawn as dashed lines.

CCDC reference: 1419383

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1O4	0.86	1.91	2.587(3)	135
N2H2O8	0.86	1.89	2.575(2)	135
O1H1CO5ⁱ	0.82	1.90	2.715(3)	172
O2H2CO8ⁱⁱ	0.82	1.77	2.589(3)	173
O3H3O6ⁱⁱⁱ	0.82	1.91	2.706(3)	163
O5H5O4^iv	0.82	1.84	2.650(2)	171
O6H6O2^v	0.82	1.81	2.609(2)	163
O7H7O3^vi	0.82	2.19	2.972(2)	159

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

Acknowledgments

We gratefully acknowledge the Natural Science Foundation of Shanxi province (grant No. 2015011107), the Research Fund for the Doctoral Program of Shanxi University of Traditional Chinese Medicine (2014) and the College Student’s Innovation Traning Project of Shanxi Province (grant No. 2013319).

supplementary crystallographic information

S1. Structural commentary

Schiff bases have been receiving considerable attention for many years, mainly due to their importance as ligands in metal complexes with special magnetic (Weber et al., 2007) and selective fluorescence sensor (Dong et al., 2014; Liu et al. , 2014), catalytic (Chen et al., 2008) and biological properties (May et al., 2004).

As a part of our studies on the synthesis and structural properties of Schiff bases with naphthaldehyde and methylamine, we have determined the structure of the title compound (Fig. 1). Some examples of related structures already appear in the literature (Wang et al., 2011; Kennedy et al., 2013; Abu-Dief et al., 2015). The structure of the title compound contains two molecules in the asymmetric unit (Fig. 1) in contrast to the polymorph in which there is a single molecule (Martínez et al., 2011). Both molecules in the title compound are in the trans form. In the crystal, N—H···O and O—H···O hydrogen bonds connect molecules forming a two-dimensional network parallel to (001) (Fig. 2).

S2. Synthesis and crystallization

An ethanol solution (10 mL) of tris(hydroxymethyl)aminomethane (tris, 0.1 mol, 0.1211g) was added to another ethanol (10mL) containing 2-hydroxy-1-naphthaldehyde (0.1 mol, 0.1728 g), Then the solution was refluxed for 2 h and cooled to room temperature. The mixture was filtered and dried under vacuum. The title compound was crystallized as block crystals from a solution of ethanol by slow evaporation.

S3. Refinement details

All H atoms were visible in differnce Fourier maps and the presence of those bonded bonded to N1 and N2 confirm the enolate form. Utimately, all H atoms were placed in calculated positions with C—H = 0.93–0.97Å, N—H = 0.86Å and O—H = 0.82Å and were included in the refinment in a riding-motion approximation with U_iso(H)=1.2U_eq(C,N) and U_iso(H)=1.5U_eq(O).