(2,7-Dimeth­oxy­naphthalen-1-yl)(2,4,6-trimethyl­phen­yl)methanone

Toyokazu Muto; Kosuke Sasagawa; Akiko Okamoto; Hideaki Oike; Noriyuki Yonezawa

doi:10.1107/S1600536811039225

. 2011 Sep 30;67(Pt 10):o2813. doi: 10.1107/S1600536811039225

(2,7-Dimethoxynaphthalen-1-yl)(2,4,6-trimethylphenyl)methanone

Toyokazu Muto ^a, Kosuke Sasagawa ^a, Akiko Okamoto ^a,^*, Hideaki Oike ^a, Noriyuki Yonezawa ^a

PMCID: PMC3201449 PMID: 22064621

Abstract

In the title compound, C₂₂H₂₂O₃, the dihedral angle between the naphthalene ring system and the benzene ring is 82.93 (5)°. The bridging carbonyl C—C(=O)—C plane makes dihedral angles of 50.11 (6) and 46.87 (7)°, respectively, with the naphthalene ring system and the benzene ring. In the crystal, three types of weak intermolecular C—H⋯O interactions are observed.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Muto et al. (2010 ▶); Watanabe et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₂₂H₂₂O₃
M _r = 334.40
Monoclinic,
a = 10.5238 (4) Å
b = 12.2289 (4) Å
c = 15.0504 (5) Å
β = 111.340 (2)°
V = 1804.11 (11) Å³
Z = 4
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 193 K
0.50 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.739, T _max = 0.882
32585 measured reflections
3295 independent reflections
2945 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.112
S = 1.08
3295 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 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 datablock(s) I, global. DOI: 10.1107/S1600536811039225/zk2031sup1.cif

e-67-o2813-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039225/zk2031Isup2.hkl

e-67-o2813-Isup2.hkl^{(158.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039225/zk2031Isup3.cml

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
C4—H4⋯O1ⁱ	0.95	2.54	3.3756 (18)	147
C7—H7⋯O2ⁱⁱ	0.95	2.60	3.466 (2)	152
C18—H18B⋯O3ⁱⁱⁱ	0.98	2.59	3.471 (2)	149

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

Acknowledgments

The authors express their gratitude to Master Daichi Hijikata, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture and Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice.

supplementary crystallographic information

Comment

In the course of our study on electrophilic aromatic acylation of 2,7-dimethoxynaphthalene, peri-arylcarbonylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009; Okamoto, Mitsui et al., 2011). Recently, we have reported the crystal structures of several 1,8-diarylcarbonylated naphthalene analogues exemplified by 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., 2010). The arylcarbonyl groups at the 1,8-positions of the naphthalene rings in these compounds are connected in an almost perpendicular fashion. Besides, the crystal structures of arylcarbonylated naphthalene homologues, 1-monoarylcarbonylated naphthalene compounds and the β-isomers of 3-monoarylcarbonylated naphthalene compounds, have been also clarified such as (2,7-dimethoxynaphthalen-1-yl)(4-fluorophenyl)methanone (Watanabe et al., 2011) and (3,6-dimethoxy-2-naphthyl)(4-fluorobenzoyl)methanone (Watanabe, Muto, Nagasawa et al., 2010).

As a part of our continuing study on the molecular structures of these homologous molecules, the crystal structure of title compound, 1-monoarylcarbonylnaphthalene bearing three methyl groups on the arylcarbonyl group, is discussed in this report.

The molecular structure of the title compound is displayed in Fig. 1. The 2,4,6-trimethylphenyl group is out of the plane of the naphthalene ring. The dihedral angle between the best planes of the 2,4,6-trimethylphenyl ring (C12—C17) and the naphthalene ring (C1—C10) is 82.93 (5)°. The carbonyl group makes torsion angles of -130.97 (14) and -131.79 (13)°, respectively, with the naphthalene ring and the benzene ring [C2—C1—C11—O1 torsion angle = -130.97 (14)°; O1—C11—C12—C13 torsion angle = -131.79 (13)°]. In addition, two types of intramolecular C—H···O interactions are observed (C9—H9···O1 = 2.39 Å and C22—H22a···O1 = 2.51 Å; Fig. 1 and Table 1).

In the crystal structure, the molecular packing of the title compound is stabilized mainly by van der Waals interactions. The crystal packing is additionally stabilized by three types of C—H···O hydrogen bondings: Intermolecular C—H···O hydrogen bonding between the oxygen atom (O1) of the carbonyl group and one hydrogen atom (H4) of the naphthalene ring of the adjacent molecule is formed along the c axis (C4—H4···O1ⁱ; Fig. 2 and Table 1). There is also intermolecular C—H···O hydrogen bonding between the oxygen atom (O2) of 2-methoxy group and one hydrogen atom (H7) of the naphthalene ring of the adjacent molecule along the b axis (C7—H7···O2ⁱⁱ; Fig. 3 and Table 1). Furthermore, an intermolecular C—H···O hydrogen bonding between the oxygen atom (O3) of the 7-methoxy group and one hydrogen atom (H18b) of the 2-methoxy group of the adjacent molecule along the ac diagonal (C18—H18b···O3 ⁱⁱⁱ; Fig. 4 and Table 1) is observed.

Experimental

To a 10 ml flask, 2,4,6-trimethylbenzoyl chloride (0.55 mmol, 100 mg), aluminium chloride (0.60 mmol, 80.0 mg) and methylene chloride (1.25 ml) were placed and stirred at 273 K. To the reaction mixture thus obtained, 2,7-dimethoxynaphthalene (0.50 mmol, 94.0 mg) was added. After the reaction mixture was stirred at 273 K for 6 h, it was poured into ice-cold water (10 ml). The aqueous layer was extracted with CHCl₃ (10 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake. The crude product was purified by recrystallization from methanol (yield 56%). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from hexane and CHCl₃.