2,2′-[(Propane-1,3-diyldinitrilo)bis­(phenyl­methyl­idyne)]diphenol

Robert S Black; David G Billing; Agata Bartyzel; Ewa Cukrowska

doi:10.1107/S1600536810011189

. 2010 Mar 31;66(Pt 4):o1002–o1003. doi: 10.1107/S1600536810011189

2,2′-[(Propane-1,3-diyldinitrilo)bis(phenylmethylidyne)]diphenol

Robert S Black ^a, David G Billing ^a,^*, Agata Bartyzel ^a,^‡, Ewa Cukrowska ^a

PMCID: PMC2983949 PMID: 21580567

Abstract

In the title molecule, C₂₉H₂₆N₂O₂, there are two strong intramolecular O—H⋯N hydrogen bonds involving the hydroxy and imine groups, forming S(6) ring motifs. The dihedral angles between adjacent phenyl rings and phenol-containing planes are 85.27 (19) and 91.38 (18)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds connect molecules into a two-dimensional network.

Related literature

The title compound forms part of the group of Schiff bases with a similar method of synthesis as described in Schilf et al. (2007 ▶). The intermolecular hydrogen bonds O—H⋯N between the hydroxy and imine are common to this type of compound as shown with the series of compounds reported by Fernández et al. (2001 ▶); Kabak (2003 ▶); Wojciechowski et al. (2001 ▶); Dey et al. (2001 ▶); Koşar, et al. (2004 ▶); Lu, et al. (2008 ▶); Qiu & Zhao (2008 ▶); Montazerozohori et al. (2009 ▶); Corden et al. (1996 ▶). For a decription of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₉H₂₆N₂O₂
M _r = 434.52
Monoclinic,
a = 18.226 (2) Å
b = 8.2303 (9) Å
c = 18.642 (2) Å
β = 119.086 (5)°
V = 2443.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.7 × 0.5 × 0.28 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
21350 measured reflections
5896 independent reflections
3749 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.173
S = 1.03
5896 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: SMART-NT (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011189/lh5012sup1.cif

e-66-o1002-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011189/lh5012Isup2.hkl

e-66-o1002-Isup2.hkl^{(282.8KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.80	2.5344 (17)	148
O2—H2A⋯N2	0.82	1.81	2.5431 (18)	148
C17—H17⋯O2ⁱ	0.93	2.56	3.481 (2)	168
C18—H18⋯O1ⁱⁱ	0.93	2.47	3.395 (3)	174
C21—H21⋯O2ⁱⁱⁱ	0.93	2.56	3.492 (2)	175

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

Acknowledgments

The University of the Witwatersrand and the National Research Foundation (GUN 2069064) are thanked for providing the infrastructure and for the award of a research grant required to carry out this work.

supplementary crystallographic information

Comment

The molecular structure of the title compound is shown in Fig. 1. There are two strong intramolecular O—H..O hydrogen bonds involving the hydroxyl and imine groups forming S(6) ring motifs (Bernstein et al., 1995). These types of hydrogen bonds are common to some reported molecular structures (Schilf et al., 2007; Fernández et al., 2001; Kabak, 2003; Wojciechowski et al., 2001; Dey et al., 2001; Koşar, et al., 2004; Lu, et al., 2008; Qiu & Zhao, 2008; Montazerozohori et al., 2009; Corden et al., 1996). In the crystal structure, weak intermolecular C—H···O hydrogen bond connect molecules to form a two-dimensional network.

Experimental

A mixture of 1.0 mmol (2.00 g) of 2-hydroxybenzophenone, 0.5 mmole (0.42 cm³) of 1,3-propanediamine and 2 drops of glacial acetic acid in 40 ml of methanol was refluxed for 8 h. The excess of solvent (ca. 30 ml) was then evaporated. After cooling to 277 K a yellow solid was produced. The polycrystalline product was collected by filtration, washed with methanol and dried. A yield of 52% was obtained. Recrystalization from an ethanol solution yielded single crystals suitable for x-ray diffraction. Elemental analysis C% 79.67 H% 6.26 N% 6.11%.