2-Methyl­anilinium 3,4,5,6-tetra­bromo-2-(meth­oxy­carbon­yl)benzoate methanol monosolvate

Li, J.

doi:10.1107/S1600536811008543

Volume 67
Part 4
Page o900
April 2011

Received 13 February 2011
Accepted 6 March 2011
Online 15 March 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R = 0.037
wR = 0.072
Data-to-parameter ratio = 15.4
Details

2-Methylanilinium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol monosolvate

Jian Li ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
Correspondence e-mail: ljwfu@163.com

In the anion of the title compound, C₇H₁₀N⁺·C₉H₃Br₄O₄^-·CH₃O, the dihedral angles formed by the benzene ring and the mean planes of the carboxylate and methoxycarbonyl groups are 74.8 (5) and 75.0 (5)°, respectively. In the crystal, intermolecular N-HO and O-HO hydrogen bonds link the components into chains along [100]. Additional stabilization is provided by weak intermolecular C-HO hydrogen bonds.

Related literature

For related structures, see: Li (2011); Liang (2008).

Experimental

Crystal data

C₇H₁₀N⁺·C₉H₃Br₄O₄^-·CH₄O
M_r = 634.96
Monoclinic, P 2₁ /c
a = 8.1909 (8) Å
b = 13.5551 (12) Å
c = 19.5082 (16) Å
= 90.371 (1)°
V = 2165.9 (3) Å³
Z = 4
Mo K radiation
= 7.46 mm^-1
T = 298 K
0.40 × 0.32 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997) T_min = 0.154, T_max = 0.229
10672 measured reflections
3811 independent reflections
2507 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.072
S = 1.07
3811 reflections
248 parameters
H-atom parameters constrained
_max = 0.71 e Å^-3
_min = -0.59 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO5ⁱ	0.89	1.87	2.756 (6)	178
N1-H1BO4ⁱ	0.89	1.87	2.746 (5)	170
O5-H5O3ⁱⁱ	0.82	1.83	2.645 (5)	173
C15-H15O5ⁱ	0.93	2.55	3.281 (7)	135
C17-H17BO2	0.96	2.47	3.296 (9)	144
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5212 ).

Acknowledgements

The author thanks Shandong Provincial Natural Science Foundation, China (ZR2009BL027) for support.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, J. (2011). Acta Cryst. E67, o200.
Liang, Z.-P. (2008). Acta Cryst. E64, o2416.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds