2,7-Bis(4-acetyl­phen­oxy)naphthalene

Kosuke Nakaema; Masahiro Imaizumi; Keiichi Noguchi; Noriyuki Yonezawa

doi:10.1107/S1600536808007496

. 2008 Mar 29;64(Pt 4):o747. doi: 10.1107/S1600536808007496

2,7-Bis(4-acetylphenoxy)naphthalene

Kosuke Nakaema ^a, Masahiro Imaizumi ^b, Keiichi Noguchi ^c, Noriyuki Yonezawa ^a,^*

PMCID: PMC2960926 PMID: 21202137

Abstract

The title compound, C₂₆H₂₀O₄, has an asymmetrical conformation at 193 K. The 4-acetylphenyl groups are twisted away from the the naphthalene ring system, with one benzene ring turned towards the 1-position of the naphthalene ring and the other benzene ring turned towards the 6-position. The interplanar angles between the mean planes of the benzene rings and the naphthalene ring system are 68.71 (6) and 74.01 (6)°. The structure displays C—H⋯O hydrogen bonding and π–π stacking interactions [centroid–centroid and interplanar distances are 3.5938 (9) and 3.517 Å, respectively].

Related literature

For related literature, see: Ocak et al. (2004 ▶).

Experimental

Crystal data

C₂₆H₂₀O₄
M _r = 396.42
Triclinic,
a = 5.8691 (2) Å
b = 7.9105 (2) Å
c = 21.4040 (5) Å
α = 90.322 (2)°
β = 95.534 (2)°
γ = 102.283 (2)°
V = 966.11 (5) Å³
Z = 2
Cu Kα radiation
μ = 0.74 mm⁻¹
T = 193 K
0.60 × 0.20 × 0.02 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.792, T _max = 0.985
17040 measured reflections
3467 independent reflections
2617 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.125
S = 1.09
3467 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla, et al, 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007496/fl2193sup1.cif

e-64-0o747-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007496/fl2193Isup2.hkl

e-64-0o747-Isup2.hkl^{(166.5KB, 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
C2—H2⋯O2ⁱ	0.95	2.54	3.448 (2)	160

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

supplementary crystallographic information

Comment

An ORTEPIII (Burnett & Johnson, 1996) plot of the molecule (I) is shown in Fig. 1.Considering its two dimensional representation, the molecule could have had C₂ symmetry. This is certainly not the case in practice, as the naphthalene moiety forms dihedral angles of 68.71 (6)° and 74.01 (6)° with the best mean planes of the aromatic rings C11—C16 and C19—C24, respectively. The torsion angles between the naphthalene ring and the two benzene rings are -34.0 (2)° [C11—O1—C1—C2], and -132.00 (15)° [C19—O3—C5—C4]. The difference in the two torsion angles between the naphthalene and benzene rings is rather large. This means that one benzene ring (C11—C16) turns to the 1-position, and the other benzene ring (C19—C24) turns to the 6-position rather than the 8-position. This compound has an asymmetrical conformation similar to that of 2,7-bis(3,4-dicyanophenoxy)naphthalene (Ocak et al., 2004).

The crystal packing is stabilized mainly by van der Waals interactions, however there is some π—π stacking and C—H···O intermolecular interactions (Table 1, Fig. 2). The hydrogen bonds between an acetyl hydrogen and the carbonyl oxygen of a neighboring molecule link the molecules into pairs around a center of symmetry that are aligned complementarily in a row forming a polymer-like infinitive ribbon (Fig. 2).

Experimental

2,7-naphthalenediol (160 mg, 1.0 mmol) and 4-fluoroacetophenone (303 mg, 2.2 mmol) were dissolved in DMF (1.0 ml) with stirring under N₂. Potassium carbonate (304 mg, 2.2 mmol) was added. The reaction mixture was stirred for 24 h at 150 C° and poured into water. The products extracted with CHCl₃, and washed with brine. The organic layer was dried with MgSO₄ and concentrated under pressure. Slightly purplish single crystals suitable for X-ray diffraction were obtained by crystallization from ethanol.