7-Methoxy-1-{[(Z)-3-nitrophenylimino](phenyl)methyl}-2-naphthol

Atsushi Nagasawa; Akiko Okamoto; Noriyuki Yonezawa

doi:10.1107/S1600536810039358

. 2010 Oct 9;66(Pt 11):o2738. doi: 10.1107/S1600536810039358

7-Methoxy-1-{[(Z)-3-nitrophenylimino](phenyl)methyl}-2-naphthol

Atsushi Nagasawa ^a, Akiko Okamoto ^a, Noriyuki Yonezawa ^a,^*

PMCID: PMC3009002 PMID: 21588945

Abstract

In the title compound, C₂₄H₁₈N₂O₄, the phenyl and benzene rings are both oriented almost perpendicular to the naphthalene ring system at dihedral angles of 70.97 (5) and 84.64 (5)°. The former rings make a dihedral angle of 87.15 (6)°. The molecule has a Z configuration about the C=N bond. In the crystal, molecules are connected by a pair of intermolecular O—H⋯O hydrogen bonds between the hydroxy and the nitro group, forming centrosymmetric dimers. Intermolecular C—H⋯O interactions also occur.

Related literature

For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Watanabe et al. (2010 ▶); Mitsui et al. (2008 ▶); Nagasawa et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₂₄H₁₈N₂O₄
M _r = 398.40
Triclinic,
a = 9.6709 (10) Å
b = 9.8345 (10) Å
c = 10.397 (1) Å
α = 88.640 (3)°
β = 89.194 (3)°
γ = 82.126 (3)°
V = 979.19 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.50 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.955, T _max = 0.982
15901 measured reflections
4475 independent reflections
3923 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.156
S = 1.13
4475 reflections
277 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.40 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/S1600536810039358/pk2274sup1.cif

e-66-o2738-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039358/pk2274Isup2.hkl

e-66-o2738-Isup2.hkl^{(214.8KB, 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
O1—H1⋯O3ⁱ	0.83 (2)	2.05 (2)	2.8559 (17)	163 (18)
C19—H19⋯O1	0.95	2.56	3.3241 (16)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice.

supplementary crystallographic information

Comment

Recently, we reported crystal structures of several 1-monoaroylnaphthalene derivatives exemplified by 2-(2,7-dimethoxy-1-naphthoyl)benzoic acid (Hijikata et al., 2010), 2,7-dimethoxy-1-(4-nitrobenzoyl)-naphthalene (Watanabe et al., 2010) and (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al., 2008). Furthermore, we also reported the crystal structure of 1-[(4-chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol-1,4-diazabicyclo[2.2.2]octane (2/1) (Nagasawa et al., 2010a) that formed 2:1 comolecular unit of triarylimine and 1,4-diazabicyclo[2.2.2]octane (DABCO). As a part of the continuous study on the molecular structures of this kind of homologous molecules, we have investigated imination reaction of aroylated naphthalene. The title compound was prepared from (2-hydroxy-7-methoxynaphthalen-1-yl)(phenyl)methanone (Nagasawa et al., 2010b) and 3-nitroaniline in the presence of TiCl₄ and DABCO.

An ORTEPIII (Burnett & Johnson, 1996) plot is shown in Fig. 1. In the molecule, interplanar angles of the least-squares plane of the benzene ring (C12–C17) attached to nitrogen atom (N1) and benzene ring (C18–C23) attached to carbon atom (C11) of imine moiety against the naphthalene ring (C1–C10) are 70.97 (5) and 84.64 (5)°, respectively. Furthermore, the interplanar angle between two benzene rings is 87.15 (6)°. The molecule has a Z configuration for the imine vector.

In the crystal structure, the molecular packing is mainly stabilized by intermolecular hydrogen bond and van der Waals interactions. The intermolecular O—H···O hydrogen bond between the hydorxy and nitro groups on the naphthalene ring and the N-aryl group along the c axis, is observed [H1···O3 = 2.05 (2) Å] (Fig. 2). The carbon atom in the naphthalene ring interacts with an oxygen atom in the nitro groups [C8···O4 = 3.079 (2) Å] along the c axis (Fig. 3). One hydrogen atom on a phenyl group has a close contact with the hydrogen atom on the phenyl group of the next molecule [H16···H17 = 2.27 Å], roughly along the a axis.

Experimental

To a solution of (2-hydroxy-7-methoxynaphthalen-1- yl)(phenyl)methanone (0.2 mmol, 56 mg) in chlorobenzene (1 ml), a mixture of 3-nitroaniline (0.22 mmol, 30 mg), TiCl₄ (0.33 mmol, 62.4 mg), DABCO (1.32 mmol, 148.0 mg) and chlorobenzene (1 ml) was added by portions at 363 K under nitrogen atmosphere. After the reaction mixture was stirred at 398 K for 1.5 h, the resulting solution was filtered to remove the precipitate. The solvent was removed under reduced pressure to give crude material. The crude material thus obtained was subjected to crystallization from CHCl₃/hexane to give compind (I) as yellow platelets (m.p. 508.5–509.0 K, yield 28 mg, 35%).

Spectroscopic Data: ¹H NMR (300 MHz, DMSO-d₆) δ; 10.23, (s, 1H), 7.69–7.60 (m, 6H), 7.49–7.38 (m, 3H), 7.30–7.26 (m, 2H), 6.97 (d, 1H), 6.84 (dd, 1H), 6.54 (d, 1H), 3.66 (s, 3H); ¹³C NMR (75 MHz, DMSO-d₆) 168.5, 158.7, 154.1, 152.8, 148.0, 138.3, 132.5, 131.9, 131.0, 130.5, 130.1, 129.2, 128.7, 126.6, 123.1, 118.7, 115.6, 115.2, 114.8, 114.2, 102.6, 55.6; IR (KBr): 3416, 3073, 1626, 1614, 1511, 1341, 1210; HRMS (m/z): [M + H]⁺ calcd for C₂₄H₁₉N₂O₄, 399.1345; found, 399.1349.