(Pyridine-2,6-diyldimethyl­ene)bis­(diphenyl­methanol)

Wei-Jin Gu; Bing-Xiang Wang

doi:10.1107/S1600536808043572

. 2009 Jan 8;65(Pt 2):o233. doi: 10.1107/S1600536808043572

(Pyridine-2,6-diyldimethylene)bis(diphenylmethanol)

Wei-Jin Gu ^a,^*, Bing-Xiang Wang ^a

PMCID: PMC2968384 PMID: 21581850

Abstract

In the title compound, C₃₃H₂₉NO₂, the central pyridyl ring makes dihedral angles of 42.71 (16), 44.78 (16), 85.47 (12) and 76.74 (12)° with the four phenyl rings. There are two intramolecular O—H⋯N hydrogen bonds. In the crystal structure, molecules are linked into a chain running along the b axis by a weak C—H⋯π interaction.

Related literature

For organometallic pincer complexes, see: Dupont et al. (2005 ▶); Gauvin et al. (2001 ▶); Haenel et al. (2001 ▶); van der Boom & Milstein (2003 ▶); van der Boom et al. (1997 ▶); Vigalok & Milstein (2001 ▶); Bergbreiter et al. (1999 ▶). The title compound was prepared according to the procedure described by Berg & Holm (1985 ▶).

Experimental

Crystal data

C₃₃H₂₉NO₂
M _r = 471.57
Monoclinic,
a = 18.492 (3) Å
b = 10.1039 (17) Å
c = 16.097 (3) Å
β = 121.234 (2)°
V = 2571.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.980, T _max = 0.982
10905 measured reflections
2960 independent reflections
2695 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.127
S = 1.04
2960 reflections
331 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536808043572/is2375sup1.cif

e-65-0o233-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043572/is2375Isup2.hkl

e-65-0o233-Isup2.hkl^{(145.3KB, 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—H1⋯N1	0.82 (5)	2.34 (5)	3.013 (4)	139 (4)
O2—H2A⋯N1	0.82 (5)	2.20 (5)	2.854 (4)	136 (4)
C31—H31⋯Cg1ⁱ	0.93	3.08	3.973 (3)	162

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Symmetry code: (i) Inline graphic . Cg1 is the centroid of the C8–C13 ring.

Acknowledgments

We thank the Natural Science Foundation of Jiangsu Higher Education Institutions of China (grant No. 07KJD150101) for financial support.

supplementary crystallographic information

Comment

Currently, organometallic pincer complexes attract much attention because of their widespread applications in catalysis and material sciences (Dupont et al., 2005; van der Boom & Milstein, 2003). Major recent findings have been the generation of efficient dehydrogenation (Haenel et al., 2001) and Heck type catalysts (Bergbreiter et al., 1999), activation of strong C—O (van der Boom et al., 1997) and C—C bonds (Gauvin et al., 2001), and trapping of various intermediates and unusual molecules (Vigalok & Milstein, 2001). 2,6-Bis(2-hydroxy-2,2-diphenylethyl)pyridine, (I), could coordinate with transition metals to form pincer complexes. In our studies, we have got its single crystals and herein reported its crystal structure.

The crystal structure of title compound, C₃₃H₂₉NO₂, reveals that all the bond lengths and angles have normal values. Each asymmetric unit in (I) contains four phenyl rings A (C8—C13), B (C14—C19), C (C22—C27) D (C28—C33) and a pyridyl ring E (N1/C1—C5). The rings A, B, C, D and E are all not coplanar, their dihedral angles between rings A and B, B and E, E and C, C and D being 68.13 (15), 44.79 (16), 85.48 (11) and 86.85 (14)°, respectively. The dihedral angles between rings A and E, B and E, C and E, D and E are 42.71 (16), 44.78 (16), 85.47 (12) and 76.74 (12)°, respectively. In the molecule there are two intramolecular O—H···N hydrogen bonds (Table 1 and Fig. 1). In the crystal, there is a weak C—H···π interaction (C31—H31···Cg1ⁱ, i: x, -1 + y, z; Cg1 is the centroid of ring A) between the neighbouring molecules (Table 1). Through the weak C—H···π interactions, the one-dimensional chains are formed along the b axis (Fig. 2).

Experimental

2,6-Bis(2-hydroxy-2,2-diphenylethyl)pyridine was prepared by 2,6-lutidine and benzophenone (yield 30%) according to a procedure described in the literature (Berg & Holm, 1985). Colorless crystals were obtained by recrystallized from light petroleum-ethyl acetate (v/v 5/1) at room temperature.

¹H-NMR (CDCl₃, 400 MHz) δ: 7.17–7.37 (21 H, m, 4Ph + 4-H), 6.69 (2 H, d, J = 7.5 Hz, 3-H + 5-H), 5.25 (2 H, s, 2OH), 3.68 (4 H, s, 2CH₂).