N,N′-Bis(4-chloro­phen­yl)naphthalene-1,4-dicarboxamide N,N-dimethyl­formamide disolvate

Lin-Hai Jing

doi:10.1107/S1600536809034394

. 2009 Sep 9;65(Pt 10):o2414. doi: 10.1107/S1600536809034394

N,N′-Bis(4-chlorophenyl)naphthalene-1,4-dicarboxamide N,N-dimethylformamide disolvate

Lin-Hai Jing ^a,^*

PMCID: PMC2970211 PMID: 21577873

Abstract

In the title compound, C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO, the two C=O groups adopt an anti orientation. The two amide groups are twisted away from the naphthalene ring system by 59.10 (4) and 68.22 (4)°. The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the use of 1,4-naphthalenedicarboxylic acid derivatives in the preparation of polymers, see: Fukuzumi et al. (1994 ▶); Tsukada et al. (1994 ▶). For related structures, see: Jing (2008 ▶); Jing et al. (2006a ▶,b ▶).

Experimental

Crystal data

C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO
M _r = 581.48
Triclinic,
a = 12.040 (3) Å
b = 12.121 (3) Å
c = 12.295 (3) Å
α = 101.75°
β = 111.843 (3)°
γ = 110.833 (2)°
V = 1435.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 93 K
0.40 × 0.33 × 0.30 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
11770 measured reflections
6317 independent reflections
5120 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.095
S = 1.00
6317 reflections
373 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536809034394/ci2896sup1.cif

e-65-o2414-sup1.cif^{(25KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034394/ci2896Isup2.hkl

e-65-o2414-Isup2.hkl^{(309.2KB, 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⋯O4ⁱ	0.85 (2)	2.01 (2)	2.8536 (17)	173 (2)
N2—H2N⋯O3	0.89 (2)	2.02 (2)	2.9040 (17)	168 (2)
C23—H23⋯O4	0.95	2.39	3.3258 (19)	167
C2—H2⋯O3ⁱⁱ	0.95	2.54	3.4458 (19)	160
C6—H6⋯O2ⁱⁱⁱ	0.95	2.38	3.3214 (19)	169
C16—H16⋯O3ⁱ	0.95	2.54	3.3949 (19)	151
C21—H21⋯O1^iv	0.95	2.37	3.1719 (19)	142

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

Acknowledgments

The author thanks 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 crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing et al., 2006a), N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing et al., 2006b) and N,N'-bis(4-methylphenyl)-1,4-naphthalenedicarboxamide N,N-dimethylacetamide disolvate (Jing, 2008). We now report the crystal structure of the title compound.

Bond lengths and angles in the molecules are normal. The naphthalene ring system is planar, with a maximum deviation of 0.056 (1) Å for atom C2. Two C═O groups exhibit an anti orientation. 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/C18 planes form dihedral angles of 59.10 (4) and 68.22 (4)°, respectively, with the C1-C10 plane. The O1/N1/C1/C11 and C12—C17 planes are inclined at an angle of 12.15 (8)° while the O2/N2/C4/C18 and C19—C24 planes make a dihedral angle of 11.22 (9)°. 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-Chloroaniline (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 6 h. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate obtained was dissolved in dimethylformamide and allowed to stand for one month at ambient temperature, after which time colourless single crystals suitable for X-ray diffraction were obtained.