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Volume 66 
Part 1 
Page o27  
January 2010  

Received 17 November 2009
Accepted 29 November 2009
Online 4 December 2009

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.029
wR = 0.065
Data-to-parameter ratio = 13.4
Details
Open access

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

aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: jhrkk20060220@yahoo.com.cn

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[Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06298919.]); Tsukada et al. (1994[Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06298918.]). For the crystal structure of the 4-methylphenyl analog, see: Jing (2008[Jing, L.-H. (2008). Acta Cryst. E64, o2379.]).

[Scheme 1]

Experimental

Crystal data
  • C24H16Br2N2O2·2C4H9NO

  • Mr = 698.45

  • Triclinic, [P \overline 1]

  • a = 10.4589 (9) Å

  • b = 12.4485 (5) Å

  • c = 12.8439 (11) Å

  • [alpha] = 90.775 (2)°

  • [beta] = 111.370 (4)°

  • [gamma] = 92.944 (2)°

  • V = 1554.3 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.364, Tmax = 0.637

  • 12655 measured reflections

  • 6836 independent reflections

  • 5420 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.065

  • S = 0.95

  • 6836 reflections

  • 509 parameters

  • 64 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.73 e Å-3

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
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+1, -z+2.

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2967 ).


Acknowledgements

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

References

Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06298919.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Jing, L.-H. (2008). Acta Cryst. E64, o2379.  [CSD] [CrossRef] [details]
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06298918.


Acta Cryst (2010). E66, o27  [ doi:10.1107/S1600536809051447 ]

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