{2,7-Dieth­oxy-8-[(naphthalen-1-yl)carbon­yl]naph­thalen-1-yl}(naphthalen-1-yl)methanone

Takehiro Tsumuki; Ryo Takeuchi; Hiroyuki Kawano; Noriyuki Yonezawa; Akiko Okamoto

doi:10.1107/S1600536813005710

. 2013 Mar 6;69(Pt 4):o495–o496. doi: 10.1107/S1600536813005710

{2,7-Diethoxy-8-[(naphthalen-1-yl)carbonyl]naphthalen-1-yl}(naphthalen-1-yl)methanone

Takehiro Tsumuki ^a, Ryo Takeuchi ^a, Hiroyuki Kawano ^b, Noriyuki Yonezawa ^a, Akiko Okamoto ^a,^*

PMCID: PMC3629527 PMID: 23634045

Abstract

In the title compound, C₃₆H₂₈O₄, the 1-naphthoyl groups at the 1- and 8-positions of the central 2,7-diethoxynaphthalene ring system are aligned almost antiparallel and make a dihedral angle of 76.59 (4)°. The dihedral angles between the central 2,7-diethoxynaphthalene ring system and the terminal naphthalene ring systems are 86.48 (4) and 83.97 (4)°. In the crystal, C—H⋯π interactions between the central naphthalene ring systems and the naphthoyl groups are observed along the a axis, with the molecules forming a columnar structure. The columns are linked into chains parallel to the b axis by C—H⋯O interactions.

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Nakaema et al. (2008 ▶); Tsumuki et al. (2011 ▶); Sakamoto et al. (2012 ▶); Isogai et al. (2013 ▶); Tsumuki et al. (2013 ▶); Yoshiwaka et al. (2013 ▶).

Experimental

Crystal data

C₃₆H₂₈O₄
M _r = 524.58
Triclinic,
a = 8.76532 (16) Å
b = 11.4266 (2) Å
c = 14.1972 (3) Å
α = 99.080 (1)°
β = 99.036 (1)°
γ = 104.277 (1)°
V = 1331.94 (4) Å³
Z = 2
Cu Kα radiation
μ = 0.67 mm⁻¹
T = 193 K
0.60 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.689, T _max = 0.877
24143 measured reflections
4800 independent reflections
4142 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.106
S = 1.07
4800 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); 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

Click here for additional data file.^{(26.8KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005710/pk2467sup1.cif

e-69-0o495-sup1.cif^{(26.8KB, cif)}

Click here for additional data file.^{(230.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005710/pk2467Isup2.hkl

e-69-0o495-Isup2.hkl^{(230.3KB, hkl)}

Click here for additional data file.^{(10.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813005710/pk2467Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg4 and Cg6 are the centroids of the C16–C21 and C27–C32 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg4ⁱ	0.95	2.77	3.5662 (15)	142
C7—H7⋯Cg6ⁱ	0.95	2.76	3.5662 (16)	143
C30—H30⋯O2ⁱⁱ	0.95	2.53	3.3289 (19)	142
C34—H34A⋯O1ⁱⁱⁱ	0.98	2.47	3.423 (2)	163
C35—H35B⋯O2^iv	0.99	2.59	3.5476 (17)	163

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

Acknowledgments

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by an Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant.

supplementary crystallographic information

Comment

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene ring core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009, Okamoto et al., 2011). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene analogues exemplified by 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008) and [2,7-dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone (Tsumuki et al., 2011). Furthermore, crystal structures of 1,8-diaroylnaphthalene analogues bearing various alkoxy and aryloxy groups at the 2,7-positions such as 1,8-dibenzoylnaphthalene-2,7-diyl dibenzoate (Sakamoto et al., 2012) and [8-(4-phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl)methanone (Yoshiwaka et al., 2013) have been also revealed. Some 1,8-diaroylnaphthalene compounds bearing the ethoxy group, {2,7-diethoxy-8-[(naphthalen-2-yl)-carbonyl]naphthalen-1-yl}(naphthalen-2-yl)methanone (Tsumuki et al., 2013) and (8-benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone (Isogai et al., 2013), are stabilized by the molecular packing of C—H···O interactions between the aroyl groups. As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound, the 2,7-diethoxynaphthalene bearing α-naphthoyl groups at the 1,8-positions, is reported on herein.

The molecular structure of the title molecule is illustrated in Fig.1. The two terminal naphthoyl groups are oriented in opposite directions and are twisted away from the central 2,7-diethoxynaphthalene unit. The carbonyl moieties deviate slightly from the attached naphthalene rings. The dihedral angle between the two naphthalene rings of the terminal naphthoyl groups (C12–C21 and C23–C32) is 76.59 (4)°. The dihedral angles between the terminal naphthalene rings and the central naphthalene ring (C1–C10) are 86.48 (4) and 83.97 (4)°. The torsion angles between the carbonyl moieties and the central naphthalene ring are -60.91 (16)° (C10—C1—C11—O1) and -65.50 (17)° (C10—C9—C22—O2), and those between the carbonyl moieties and the terminal naphthalene rings are -47.50 (17)° (O1—C11—C12—C21) and -46.38 (17)° (O2—C22—C23—C32).

In the molecular packing, C—H···π interactions between the central naphthalene rings and the naphthoyl groups are observed along the a axis, and form columnar structures (Fig. 2, 3 and Table 1). Each column is linked into chains along the b axis by C—H···O interactions (Fig. 4 and Table 1).

Experimental

To a solution of 1-naphthoyl chloride (630 mg, 3.3 mmol) and TiCl₄ (1.88 g, 9.9 mmol) in CH₂Cl₂ (2.5 ml), 2,7-diethoxynaphthalene (220 mg, 1.0 mmol) was added. The reaction mixture was stirred at r.t. for 3 h, then poured into ice-cold water (20 ml). The aqueous layer was extracted with CHCl₃ (20 ml × 3). The combined organic extracts were washed with 2 M aqueous NaOH (25 ml × 3) followed by washing with brine (25 ml × 3). The organic layer was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (yield 95%). The crude product was purified by recrystallization from chloroform (isolated yield 60%). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from chloroform.

¹H NMR δ (500 MHz, CDCl₃): 0.57 (6H, broad), 3.78 (4H, broad), 7.13 (2H, d, J = 9.0 Hz), 7.27–7.33 (6H, m), 7.71–7.83 (6H, m), 7.91 (2H, d, J = 9.0 Hz), 8.15 (2H, broad) p.p.m.; ¹³C NMR δ (125 MHz, CDCl₃): 14.12, 64.99, 112.73, 124.29, 124.70,125.53, 125.65, 126.45, 127.26, 127.88, 130.31, 130.52, 130.85, 132.33, 132.39,133.61, 137.15, 156.87, 199.49 p.p.m.; IR (KBr): 1658, 1607, 1512, 1471, 1275 cm^-1; HRMS (m/z): [M+H]⁺ calcd. for C₃₆H₂₉O₄, 525.2066, found, 525.2032.