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

Jing, L.-H.

doi:10.1107/S1600536808037422

Volume 64
Part 12
Page o2379
December 2008

Received 27 October 2008
Accepted 11 November 2008
Online 20 November 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
Disorder in solvent or counterion
R = 0.055
wR = 0.186
Data-to-parameter ratio = 11.5
Details

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

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: jlhjhr@yahoo.com.cn

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-HO and C-HO 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, P 2₁ /c
a = 13.270 (3) Å
b = 20.285 (4) Å
c = 12.125 (3) Å
= 101.021 (4)°
V = 3203.7 (12) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.186
S = 1.00
5652 reflections
491 parameters
166 restraints
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO4	0.86	2.02	2.880 (15)	175
N2-H2NO3ⁱ	0.86	1.99	2.821 (13)	162
C24-H24O1ⁱⁱ	0.93	2.57	3.466 (5)	163
C17-H17O1	0.93	2.33	2.911 (4)	120
C25-H25O2	0.93	2.33	2.907 (4)	120
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: CI2697 ).

Acknowledgements

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

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919.
Jing, L.-H., Qin, D.-B., Gu, S.-J., Zhang, H.-X. & Lei, G. (2006a). Acta Cryst. C62, o561-o562.
Jing, L. H., Qin, D. B., Gu, S. J., Zhang, H. X. & Mao, Z. H. (2006b). Z. Kristallogr. New Cryst. Struct. 221, 200-202.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298 918.

organic compounds