cis-2-(4-Meth­oxy­phen­yl)-4-methyl-1,2-di­hydro­naphthalen-1-ol

Alan J Lough; Mohammed-Abdul Raheem; William Tam

doi:10.1107/S1600536814007739

. 2014 Apr 12;70(Pt 5):o546. doi: 10.1107/S1600536814007739

cis-2-(4-Methoxyphenyl)-4-methyl-1,2-dihydronaphthalen-1-ol

Alan J Lough ^a,^*, Mohammed-Abdul Raheem ^b, William Tam ^b

PMCID: PMC4011258 PMID: 24860354

Abstract

The stereochemistry and regiochemistry of the title compound, C₁₈H₁₈O₂, were determined by the X-ray analysis. There are two independent molecules in the asymmetric unit in which the dihedral angles between the benzene rings are 88.31 (4) and 86.27 (4)°. The cyclohexene rings are in half-chair conformations. In the crystal, O—H⋯O hydrogen bonds link alternating types of molecules into chains along [010] with graph-set C ₂ ²(4).

Related literature

For metal-catalysed ring-opening reactions of oxanorbornadiene compounds, see: Jack et al. (2013 ▶). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₈O₂
M _r = 266.32
Orthorhombic,
a = 11.4550 (3) Å
b = 11.2239 (3) Å
c = 44.3776 (10) Å
V = 5705.6 (2) Å³
Z = 16
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 150 K
0.20 × 0.20 × 0.19 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T _min = 0.707, T _max = 0.753
34754 measured reflections
4946 independent reflections
4644 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.099
S = 1.05
4946 reflections
373 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007739/rn2124sup1.cif

e-70-0o546-sup1.cif^{(37.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007739/rn2124Isup2.hkl

e-70-0o546-Isup2.hkl^{(271.3KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814007739/rn2124Isup3.cml

CCDC reference: 995951

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1O⋯O1B	0.89 (2)	2.23 (2)	3.0346 (15)	150.6 (19)
O1B—H2O⋯O1A ⁱ	0.88 (2)	2.04 (2)	2.8973 (15)	163 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC).

supplementary crystallographic information

1. Comment

We have recently investigated the metal-catalyzed ring-opening reactions of oxanorbornadiene compounds (Jack et al., 2013). When expanding this reaction using a palladium catalyst, C1-methyl substituted oxanorbornadiene (I) (see Fig. 1) reacts with 4-methoxy-1-iodobenzene (II) in the presence of PdCl₂(PPh₃)₂, Zn, ZnCl₂, Et₃N in DMF, to give the ring-opening product (III) as a single regio- and stereoisomer. The stereochemistry and regiochemistry of the product was determined by this single-crystal X-ray analysis. Although different regio- and stereoisomers could be formed, the only ring-opening product obtained was found to have a cis stereochemistry.

There are two independent molecules [A and B] in the asymmetric unit which are shown in Fig. 2. The dihedral angles between the two benzene rings [C2–C7/C11–C16] are 88.31 (4) and 86.27 (4)°, for moleclues A and B respetively. The cyclohexene rings [C1/C2/C7—C10] are in half-chair conformations. In the crystal, O—H···O hydrogen bonds link alternating types of molecules into chains along [010] with graph-set C²₂(4) (Bernstein et al., 1995) (see Fig. 3).

2. Experimental

C1 methyl substituted oxanorbornadiene (I) (0.50 mmol) and 4-methoxy-1-iodobenzene (II) (0.55 mmol) were added into an oven-dried vial containing PdCl₂(PPh₃)₂ (0.05 mmol), Zn powder (5 mmol), ZnCl₂ (0.025 mmol), Et₃N (4 mmol) in DMF (3 ml). The vial was sealed with a screw cap and was heated at 338 K with stirring for 16 h. The crude product was purified by column chromatography (EtOAc: hexanes = 1:4) followed by recrystallization in EtOAc:hexanes = 1:1 to give the cis ring-opening (III) in 85% yield. X-ray quality crystals were grown from a solution of the title compound in EtOAc:hexanes = 1:1.