1-(4-Chloro­benzo­yl)-2,7-dimethoxy­naphthalene

Ryosuke Mitsui; Kosuke Nakaema; Keiichi Noguchi; Akiko Okamoto; Noriyuki Yonezawa

doi:10.1107/S1600536808017297

. 2008 Jun 19;64(Pt 7):o1278. doi: 10.1107/S1600536808017297

1-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalene

Ryosuke Mitsui ^a, Kosuke Nakaema ^a, Keiichi Noguchi ^b, Akiko Okamoto ^a, Noriyuki Yonezawa ^a,^*

PMCID: PMC2961834 PMID: 21202910

Abstract

In the title compound, C₁₉H₁₅ClO₃, the dihedral angle between the naphthalene ring system and the benzene ring is 72.06 (7)°. The 4-chlorophenyl group and the carbonyl group are almost coplanar. An intermolecular C—H⋯O hydrogen bond is formed between an H atom of the 4-chlorophenyl group and the O atom of one methoxy group, forming a zigzag chain along the a axis.

Related literature

For the structures of closely related compounds, see: Nakaema et al. (2007 ▶); Nakaema, Okamoto et al. (2008 ▶); Nakaema, Watanabe et al. (2008 ▶).

Experimental

Crystal data

C₁₉H₁₅ClO₃
M _r = 326.76
Orthorhombic,
a = 6.6033 (3) Å
b = 16.0751 (7) Å
c = 30.2216 (12) Å
V = 3208.0 (2) Å³
Z = 8
Cu Kα radiation
μ = 2.21 mm⁻¹
T = 296 K
0.40 × 0.15 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.617, T _max = 0.801
54984 measured reflections
2919 independent reflections
2453 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.118
S = 1.11
2919 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.33 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 I, global. DOI: 10.1107/S1600536808017297/is2299sup1.cif

e-64-o1278-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017297/is2299Isup2.hkl

e-64-o1278-Isup2.hkl^{(140.5KB, 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
C13—H13⋯O3ⁱ	0.93	2.58	3.401 (2)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Recently we have reported the structure of 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 2-(4-chlorobenzoyl)-3,6-dimethoxynaphthalene (Nakaema, Okamoto et al., 2008) and 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema, Watanabe et al., 2008). As part of our ongoing studies on the formation reaction and structure of the aroylated naphthalene derivatives synthesis and crystal structure analysis of the title compound, (I), were performed. The title compound was prepared by electrophilic aromatic aroylation reaction of 2,7-dimethoxynaphthalene with 4-chlorobenzoyl chloride.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is displayed in Fig. 1. In the molecule of (I), the interplanar angle between the benzene ring (C12—C17) and the naphthalene ring (C1—C10) is 72.06 (7)°. The carbonyl group and the 4-chlorophenyl group are almost coplanar [O1—C11—C12—C17 torsion angle = -4.4 (2)°].

In the crystal structure, the molecular packing of (I) is mainly stabilized by van der Waals interaction. The molecules of (I) are aligned consecutively in stacks along the a axis (Fig. 2). Adjacent 4-chlorophenyl groups are exactly parallel, and the perpendicular distance between these planes is 3.660 (1) Å (Fig. 3). Figure 4 shows the herring-bone packing of the naphthalene ring in the crystal. The crystal packing is additionally stabilized by intermolecular C—H···O hydrogen bonding between the methoxy oxygen and a hydrogen atom of the nearby 4-chlorophenyl group of the adjacent molecule (C13—H13···O3ⁱ; Fig. 2 and Table 1).

Experimental

To a solution of 4-chlorobenzoyl chloride (77 mg, 0.44 mmol) and AlCl₃ (64 mg, 0.48 mmol) in nitrobenzene (1.0 ml) was added a solution of 2,7-dimethoxynaphthalene (0.40 M in nitrobenzene, 1.0 ml, 0.40 mmol) drop-wise at 0 °C. The reaction mixture was stirred for 6 h at 0 °C and immediately poured into H₂O (10 ml) and CHCl₃ (5 ml). The aqueous layer was extracted with CHCl₃ (3 × 5 ml). The combined organic layers were washed with aqueous 2 M NaOH (3 × 20 ml), brine (3 × 20 ml), and dried over MgSO₄ for overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from hexanes to give the title compound as a colorless platelets (m.p. 394.5–394.8 K, yield 102 mg, 78%).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 7.87 (d, 1H), 7.78 (d, 2H), 7.72 (d, 1H), 7.39 (d, 2H), 7.15 (d, 1H), 7.02 (dd, 1H), 6.78 (d, 1H), 3.79 (s, 3H), 3.73 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 196.7, 159.0, 155.0, 139.7, 136.5, 133.0, 131.3, 130.8, 129.7, 128.8, 124.4, 121.1, 117.1, 110.1, 102.0, 56.2, 55.2; IR (KBr): 1667, 1628, 1587, 1575, 1513, 1278, 1241, 1047.

Anal. Calcd for C₁₉H₁₅ClO₃: C 69.84, H 4.63. Found: C 69.61, H 4.74.