3-(1-Hydr­oxy-2-phenyl­prop-2-en-1-yl)phenol

Ignez Caracelli; Julio Zukerman-Schpector; Fateh V Singh; Hélio A Stefani; Edward R T Tiekink

doi:10.1107/S1600536810012018

. 2010 Apr 10;66(Pt 5):o1033. doi: 10.1107/S1600536810012018

3-(1-Hydroxy-2-phenylprop-2-en-1-yl)phenol

Ignez Caracelli ^a,^*, Julio Zukerman-Schpector ^b, Fateh V Singh ^c, Hélio A Stefani ^c, Edward R T Tiekink ^d

PMCID: PMC2979021 PMID: 21579096

Abstract

Two independent pseudo-enantiomeric molecules comprise the asymmetric unit in the title compound, C₁₅H₁₄O₂. While the central O—C—C—C residue approaches planarity [torsion angles = −15.8 (3) (molecule a) and 15.4 (3)° (molecule b)], the benzene rings are approximately orthogonal [the dihedral angles formed between the benzene rings are 62.89 (12) (molecule a) and 80.15 (12)° (molecule b)]. Two-dimensional arrays in the ab plane sustained by O—H⋯O hydrogen bonding are found in the crystal structure.

Related literature

For the synthesis of the title compound and the motivation for its study, see: Singh et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₄O₂
M _r = 226.28
Orthorhombic,
a = 9.1301 (2) Å
b = 10.2026 (2) Å
c = 24.8379 (6) Å
V = 2313.67 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.27 × 0.13 × 0.13 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.883, T _max = 1
31791 measured reflections
2368 independent reflections
2150 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.084
S = 1.15
2368 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and MarvinSketch (Chemaxon, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012018/hg2665sup1.cif

e-66-o1033-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012018/hg2665Isup2.hkl

e-66-o1033-Isup2.hkl^{(114KB, 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—H1O⋯O4	0.84	1.89	2.727 (2)	175
O2—H2O⋯O1ⁱ	0.84	2.00	2.823 (2)	168
O3—H3O⋯O2ⁱⁱ	0.84	1.89	2.728 (2)	174
O4—H4O⋯O3ⁱⁱⁱ	0.84	2.02	2.825 (2)	161

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

Acknowledgments

We thank FAPESP (07/59404–2 to HAS), CNPq (472237/2008–0 to IC, 300613/2007 to HAS, and 306532/2009–3 to JZ-S) and CAPES (808/2009 to JZ-S and IC) for financial support.

supplementary crystallographic information

Comment

The title compound, (I), was prepared in connection with a study of the synthesis of α,β-epoxy ketones using a palladium-catalyzed epoxidation-oxidation sequence (Singh et al., 2010). Two independent molecules, molecule a (Fig. 1) and molecule b (Fig. 2), comprise the crystallographic asymmetric unit. Molecules a and b are related by a non-crystallographic centre of inversion. Close intramolecular O2···H9b and O4···H24b contacts which close S(6) motifs are noted, Table 1. These interactions are probably responsible for the near planarity of the O2–C7–C8–C9 and O4–C22–C23–C24 residues as seen in the respective torsion angles of -15.8 (3) and 15.4 (3)°. The benzene rings are approximately orthogonal [the dihedral angles formed between the benzene rings is 62.89 (12) ° (molecule a) and 80.15 (12) ° (molecule b)].

In the crystal packing, O–H···O interactions predominate, Table 1, and lead to the formation of two-dimensional arrays in the ab plane, Fig. 3, that stack along the c axis, Fig. 4.

Experimental

The synthesis was described in Singh et al. (2010) and crystals were grown by slow evaporation from a solution of 15% of acetyl acetate in hexane.