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

Lin-Hai Jing

doi:10.1107/S1600536809051447

. 2009 Dec 4;66(Pt 1):o27. doi: 10.1107/S1600536809051447

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

Lin-Hai Jing ^a,^*

PMCID: PMC2980233 PMID: 21580134

Abstract

The title compound, C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO, crystallizes in an anti C=O orientation. The two amide groups are twisted away from the naphthalene ring system by 62.67 (8) and 75.93 (7)°. The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds. Each of the dimethylacetamide solvent molecules is disordered over two positions, with occupancy ratios of 0.556 (7):0.444 (7) and 0.654 (7):0.346 (7).

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 the crystal structure of the 4-methylphenyl analog, see: Jing (2008 ▶).

Experimental

Crystal data

C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO
M _r = 698.45
Triclinic,
a = 10.4589 (9) Å
b = 12.4485 (5) Å
c = 12.8439 (11) Å
α = 90.775 (2)°
β = 111.370 (4)°
γ = 92.944 (2)°
V = 1554.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.65 mm⁻¹
T = 93 K
0.47 × 0.33 × 0.17 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.364, T _max = 0.637
12655 measured reflections
6836 independent reflections
5420 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.065
S = 0.95
6836 reflections
509 parameters
64 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.73 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051447/ci2967sup1.cif

e-66-00o27-sup1.cif^{(30.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051447/ci2967Isup2.hkl

e-66-00o27-Isup2.hkl^{(334.5KB, 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
N1—H1N⋯O4	0.84 (2)	2.03 (3)	2.865 (13)	170 (2)
N2—H2N⋯O3′ⁱ	0.81 (2)	2.00 (3)	2.797 (13)	171 (2)
C2—H2⋯O1ⁱ	0.95	2.50	3.423 (2)	163
C6—H6⋯O2ⁱⁱ	0.95	2.49	3.426 (2)	169
C14—H14⋯O4ⁱⁱⁱ	0.95	2.55	3.48 (2)	167

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

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, the author has reported the crystal structure of N,N'-bis(4-methylphenyl)-1,4-naphthalenedicarboxamide N,N-dimethylacetamide disolvate (Jing, 2008). The crystal structure of the title compound is now reported.

The naphthalene ring system is planar, with a maximum deviation of 0.030 (3) Å for atom C3. The 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 62.67 (8) and 75.93 (7)°, respectively, with the C1–C4/C9/C10 plane. The O1/N1/C1/C11 and C12–C17 planes are inclined at an angle of 16.21 (4)° while the O2/N2/C4/C18 and C19–C24 planes make a dihedral angle of 7.42 (3)°. 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 by reduced pressure and a yellow solid was obtained. p-Bromoaniline (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.