organic compounds
Table 1
Natural atomic charges (a.u.) for one molecule (column A) and for sets of
interacting molecules (column B).
energy is comparable with weak CÐHÁ Á ÁO hydrogen bonds
(Desiraju & Steiner, 1999).
Standard deviations originate from differences in the values obtained from
different numbers of molecules used in the calculations.
Experimental
Compound (I) was synthesized according to the method of Markish
& Arrad (1995). To an aqueous solution (200 ml) containing NaOH
(5.00 g) and 5,5-dimethylhydantoin (8.40 g), Br2 (22.050 g) was added
dropwise over a period of 1 h. The reaction temperature was kept at
284.4 (3) K and the reagents were stirred for 2 h. The resulting
precipitate was ®ltered off using a Buchner funnel and washed with
cold water [275 (1) K] until bromine was not detected in the ®ltrate.
The resulting ®ne crystalline dibromantin was dried in a vacuum
desiccator for 24 h (yield 97.3%; purity 99.8%, determined by the
iodometric method). Colourless crystals of (I) suitable for X-ray
diffraction were obtained by recrystallization from a saturated solu-
tion in water (0.22 g in 100 g H2O) at 297 (1) K (7 weeks). This may
seem to be a poor solvent as dibromantin has a low solubility in water,
but usage of organic solvents (especially alcohols) causes di-
bromantin to decompose to 5,5-dimethylhydantoin before crystals
can be obtained. Attempts to recrystallize (even from water)
commercially available dibromantin always led to growth of 5,5-di-
methylhydantoin. This was probably caused by decomposition cata-
lyzed by small amounts of decomposition products always present in
commercial dibromantin (3% w/w Fluka and 2% w/w Aldrich).
Atom
A
B
N1
Br1
N2
Br2
C1
O1
C2
O2
C3
C4
H4A
H4B
H4C
0.67729
0.28887
0.69288
0.32643
0.99779
0.68595
0.84446
0.67184
0.15930
0.45606
0.16808
0.17763
0.16591
0.69853 (6)
0.32537 (7)
0.70957 (5)
0.36190 (7)
1.01303 (3)
0.71403 (5)
0.86462 (4)
0.70829 (6)
0.15918 (11)
0.45629 (11)
0.16846 (14)
0.17725 (14)
0.16583 (14)
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GG3081). Services for accessing these data are
described at the back of the journal.
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Crystal data
3
Ê
C5H6Br2N2O2
Mr = 285.94
V = 841.06 (4) A
Z = 4
Orthorhombic, Pnma
Ê
Mo Kꢂ radiation
1
a = 7.9749 (2) A
ꢃ = 9.59 mm
T = 291.0 (3) K
Ê
b = 7.9205 (2) A
Ê
c = 13.3152 (3) A
0.12 Â 0.08 Â 0.06 mm
Data collection
Kuma KM-4 CCD area-detector
diffractometer
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
Tmin = 0.399, Tmax = 0.558
8337 measured re¯ections
815 independent re¯ections
750 re¯ections with I > 2ꢁ(I)
Rint = 0.017
Re®nement
R[F2 > 2ꢁ(F2)] = 0.016
wR(F2) = 0.040
S = 1.12
65 parameters
H-atom parameters constrained
3
Ê
Áꢄmax = 0.27 e A
3
Ê
0.56 e A
815 re¯ections
Áꢄmin
=
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È
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The author thanks Polfa Pabianice for a gift of chemicals.
This work was ®nanced by funds allocated by the Ministry of
Science and Higher Education to the Institute of General and
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 Â
Ecological Chemistry, Technical University of èodz, Poland.
ꢁ
Acta Cryst. (2007). C63, o389±o391
Rafal Kruszynski C5H6Br2N2O2 o391