N,N′-Bis(4-methyl­phen­yl)naphthalene-1,4-dicarboxamide N,N-dimethyl­acetamide disolvate

Lin-Hai Jing

doi:10.1107/S1600536808037422

. 2008 Nov 20;64(Pt 12):o2379. doi: 10.1107/S1600536808037422

N,N′-Bis(4-methylphenyl)naphthalene-1,4-dicarboxamide N,N-dimethylacetamide disolvate

Lin-Hai Jing ^a,^*

PMCID: PMC2960113 PMID: 21581351

Abstract

The title compound, C₂₆H₂₂N₂O₂·2C₄H₉NO, crystallizes in an anti C=O orientation. The two amide groups are approximately perpendicular to the naphthalene ring system [dihedral angles = 88.89 (1) and 89.08 (1)°]. Each of the dimethylacetamide solvent molecules are disordered over two positions, with occupancies of 0.655 (12):0.345 (12) and 0.531 (13):0.469 (13). The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background to the application of 1,4-naphthalenedicarboxylic acid derivatives as monomers in the preparation of polymers, see: Fukuzumi et al. (1994 ▶); Tsukada et al. (1994 ▶). For related structures, see: Jing et al. (2006a ▶,b ▶).

Experimental

Crystal data

C₂₆H₂₂N₂O₂·2C₄H₉NO
M _r = 568.70
Monoclinic,
a = 13.270 (3) Å
b = 20.285 (4) Å
c = 12.125 (3) Å
β = 101.021 (4)°
V = 3203.7 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.24 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.988
16193 measured reflections
5652 independent reflections
2347 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.186
S = 1.00
5652 reflections
491 parameters
166 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037422/ci2697sup1.cif

e-64-o2379-sup1.cif^{(31.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037422/ci2697Isup2.hkl

e-64-o2379-Isup2.hkl^{(276.7KB, 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
N1—H1N⋯O4	0.86	2.02	2.880 (15)	175
N2—H2N⋯O3ⁱ	0.86	1.99	2.821 (13)	162
C24—H24⋯O1ⁱⁱ	0.93	2.57	3.466 (5)	163
C17—H17⋯O1	0.93	2.33	2.911 (4)	120
C25—H25⋯O2	0.93	2.33	2.907 (4)	120

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

Acknowledgments

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

supplementary crystallographic information

Comment

1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing et al., 2006a) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing et al., 2006b). We now report the crystal structure of the title compound.

Bond lengths and angles in the title compound are normal. The naphthalene ring system is planar, with a maximum deviation of 0.025 (1) Å for atom C3. The two C?O gruops exhibit anti orientations. As a result of steric effects, the substituent groups at atoms C1 and C4 are twisted away from the plane of the naphthalene ring system (Fig. 1). The O1/N1/C1/C11 and O2/N2/C4/C19 planes form dihedral angles of 88.89 (1) and 89.08 (1)°, respectively, with the C1—C4/C9/C10 plane. The O1/N1/C1/C11 and C12—C17 planes are inclined at an angle of 7.48 (2)° while the O2/N2/C4/C19 and C20—C25 planes make a dihedral angle of 11.10 (2)°. The crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds (Table 1).

Experimental

Naphthalene-1,4-dicarboxylic acid (2 mmol) and an excess of thionyl chloride (6 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was obtained. P-toluidine (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 1 d. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in dimethylacetamide and allowed to stand for one month at ambient temperature, after which time colourless single crystals of the title compound suitable for X-ray diffraction were obtained.