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In the redetermined [for the previous study, see Søtofte (1976 ). Acta Chem. Scand. Ser. A, 30, 309–311] crystal structure of the title compound, C2H10N2 2+·2Br−, the H atoms have been located and the hydrogen-bonding scheme is described. The ethane-1,2-diammonium cation lies over a crystallographic inversion centre and straddles a crystallographic mirror plane with the C and N atoms in special positions. In the crystal, the cations and anions are linked by N—HBr and N—H(Br,Br) hydrogen bonds, which generate various ring and chain motifs including an R 10 5(32) loop.
Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: X-SEED (Barbour, 2001 ) and Mercury (Macrae et al., 2006 ).; software used to prepare material for publication: publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033313/hb5586sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033313/hb5586Isup2.hkl
The authors acknowledge the National Research Foundation Thuthuka programme (GUN 66314) and the University of Johannesburg for funding and facilities for this study.
Compound (I) was prepared by adding 1,2-diamino-ethane (0.50 g, 2.25 mmol) to 47% hydrobromic acid (HBr, 2 ml, 37.07 mmol, Merck) in a sample vial. The mixture was then refluxed at 363 K for 2 h. The solution was cooled at 2 K h-1 to room temperature. Colourless blocks of (I) were collected.
H atoms were clearly visible from the difference Fourier map. They were independently refined with the constraints Uiso(H) = 1.2Ueq(C) and 1.5Ueq(N). For (I), the highest peak in the final difference map is 0.80Å from Br1 and the deepest hole is 0.98Å from C1.
|C2H10N22+·2Br−||F(000) = 212|
|Mr = 221.94||Dx = 2.166 Mg m−3|
|Monoclinic, C2/m||Mo Kα radiation, λ = 0.71073 Å|
|Hall symbol: -C 2y||Cell parameters from 2937 reflections|
|a = 15.144 (2) Å||θ = 2.7–28.4°|
|b = 4.7598 (7) Å||µ = 11.80 mm−1|
|c = 4.8146 (7) Å||T = 100 K|
|β = 101.323 (2)°||Block, colourless|
|V = 340.30 (8) Å3||0.36 × 0.24 × 0.20 mm|
|Z = 2|
|Bruker APEXII CCD diffractometer||481 independent reflections|
|Radiation source: fine-focus sealed tube||475 reflections with I > 2σ(I)|
|graphite||Rint = 0.024|
|and ω scans||θmax = 28.4°, θmin = 2.7°|
|Absorption correction: multi-scan (AXScale; Bruker, 2010)||h = −20→20|
|Tmin = 0.101, Tmax = 0.201||k = −6→6|
|3261 measured reflections||l = −6→6|
|Refinement on F2||Secondary atom site location: difference Fourier map|
|Least-squares matrix: full||Hydrogen site location: difference Fourier map|
|R[F2 > 2σ(F2)] = 0.013||H atoms treated by a mixture of independent and constrained refinement|
|wR(F2) = 0.035||w = 1/[σ2(Fo2) + (0.0165P)2 + 0.5674P] where P = (Fo2 + 2Fc2)/3|
|S = 1.17||(Δ/σ)max < 0.001|
|481 reflections||Δρmax = 0.62 e Å−3|
|28 parameters||Δρmin = −0.39 e Å−3|
|0 restraints||Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4|
|Primary atom site location: structure-invariant direct methods||Extinction coefficient: 0.051 (3)|
|Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.|
|Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.|
|C1||0.47174 (14)||0.0000||0.3516 (4)||0.0119 (4)|
|N1||0.37420 (13)||0.0000||0.3658 (4)||0.0113 (4)|
|Br1||0.151104 (12)||0.0000||0.17162 (4)||0.01051 (13)|
|H1A||0.4815 (14)||0.166 (5)||0.246 (4)||0.013*|
|H2A||0.344 (2)||0.0000||0.203 (8)||0.016*|
|H2B||0.3589 (15)||0.147 (5)||0.457 (5)||0.016*|
|C1||0.0081 (9)||0.0184 (11)||0.0088 (9)||0.000||0.0007 (7)||0.000|
|N1||0.0097 (8)||0.0157 (9)||0.0079 (8)||0.000||0.0001 (7)||0.000|
|Br1||0.00972 (15)||0.01224 (16)||0.00940 (15)||0.000||0.00147 (8)||0.000|
|C1—N1||1.492 (3)||N1—H2A||0.83 (4)|
|C1—C1i||1.515 (4)||N1—H2B||0.88 (2)|
|N1—C1—C1i||109.8 (2)||C1—N1—H2A||109 (2)|
|N1—C1—H1A||106.2 (12)||C1—N1—H2B||112.5 (14)|
|C1i—C1—H1A||112.3 (12)||H2A—N1—H2B||108.7 (19)|
Symmetry codes: (i) −x+1, −y, −z+1.
|N1—H2A···Br1||0.83 (4)||2.89 (3)||3.324 (2)||115 (3)|
|N1—H2A···Br1ii||0.83 (4)||3.00 (2)||3.4808 (14)||120.(1)|
|N1—H2B···Br1iii||0.88 (2)||2.48 (2)||3.3326 (14)||163 (2)|
Symmetry codes: (ii) −x+1/2, −y−1/2, −z; (iii) −x+1/2, −y+1/2, −z+1.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5586).