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

Jing, L.-H.

doi:10.1107/S1600536809051447

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 (C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.029
wR = 0.065
Data-to-parameter ratio = 13.4
Details

N,N'-Bis(4-bromophenyl)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: 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-HO and C-HO 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, $[P \overline 1]$
a = 10.4589 (9) Å
b = 12.4485 (5) Å
c = 12.8439 (11) Å
= 90.775 (2)°
= 111.370 (4)°
= 92.944 (2)°
V = 1554.3 (2) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.024

Refinement

R[F² > 2(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
_max = 0.35 e Å^-3
_min = -0.73 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO4	0.84 (2)	2.03 (3)	2.865 (13)	170 (2)
N2-H2NO3'ⁱ	0.81 (2)	2.00 (3)	2.797 (13)	171 (2)
C2-H2O1ⁱ	0.95	2.50	3.423 (2)	163
C6-H6O2ⁱⁱ	0.95	2.49	3.426 (2)	169
C14-H14O4ⁱⁱⁱ	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); 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 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.
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06298918.

organic compounds