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The crystal structure of butane-1,4-diammonium dibromide, C4H14N22+·2Br-, exhibits ionic-inorganic layers separated by organic hydro­carbon layers. The organic hydro­carbon layers pack in a stacked herring-bone manner with hydrogen bonds to the bromide ions. The cation sits on a centre of inversion. The structure is compared with that of butane-1,4-diammonium dichloride and butane-1,4-diammonium diiodide.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053736/cf2076sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053736/cf2076Isup2.hkl
Contains datablock I

CCDC reference: 633640

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.045
  • wR factor = 0.131
  • Data-to-parameter ratio = 28.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H1C .. BR1 .. 3.32 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H1E .. BR1 .. 3.33 Ang. PLAT482_ALERT_4_B Small D-H..A Angle Rep for N1 .. BR1 .. 87.10 Deg. PLAT482_ALERT_4_B Small D-H..A Angle Rep for N1 .. BR1 .. 86.30 Deg.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.44 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1D .. BR1 .. 2.99 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.435 Tmax scaled 0.083 Tmin scaled 0.024 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2003) and pubICIF (Westrip, 2006).

Butane-1,4-diammonium dibromide top
Crystal data top
C4H14N22+·2BrF(000) = 244
Mr = 249.99Dx = 1.839 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 669 reflections
a = 4.7107 (9) Åθ = 3.0–28.3°
b = 8.5491 (15) ŵ = 8.90 mm1
c = 11.229 (2) ÅT = 293 K
β = 93.037 (4)°Block, colourless
V = 451.57 (14) Å30.44 × 0.30 × 0.28 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1113 independent reflections
Radiation source: fine-focus sealed tube942 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 28.3°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 66
Tmin = 0.056, Tmax = 0.190k = 611
2321 measured reflectionsl = 1114
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0984P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1113 reflectionsΔρmax = 1.50 e Å3
39 parametersΔρmin = 1.64 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.45 (3)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5747 (8)0.3000 (4)0.5718 (4)0.0324 (8)
H1A0.67730.25560.50730.039*
H1B0.71290.33370.63370.039*
C20.4044 (9)0.4393 (5)0.5263 (4)0.0331 (9)
H2A0.30590.48550.59130.040*
H2B0.26300.40530.46590.040*
N10.3869 (8)0.1784 (4)0.6208 (4)0.0366 (8)
H1C0.49150.09700.64590.055*
H1D0.26000.14750.56410.055*
H1E0.29710.21810.68170.055*
Br10.11369 (9)0.09905 (4)0.33855 (4)0.0370 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0310 (18)0.0311 (18)0.035 (2)0.0005 (15)0.0007 (15)0.0005 (16)
C20.035 (2)0.0295 (17)0.035 (2)0.0013 (16)0.0034 (16)0.0034 (16)
N10.0414 (19)0.0280 (16)0.0407 (19)0.0001 (14)0.0041 (14)0.0020 (14)
Br10.0416 (4)0.0366 (4)0.0327 (4)0.00146 (15)0.0021 (2)0.00391 (14)
Geometric parameters (Å, º) top
C1—N11.489 (5)C2—H2A0.970
C1—C21.510 (5)C2—H2B0.970
C1—H1A0.970N1—H1C0.890
C1—H1B0.970N1—H1D0.890
C2—C2i1.514 (8)N1—H1E0.890
N1—C1—C2111.1 (3)C1—C2—H2B109.5
N1—C1—H1A109.4C2i—C2—H2B109.5
C2—C1—H1A109.4H2A—C2—H2B108.1
N1—C1—H1B109.4C1—N1—H1C109.5
C2—C1—H1B109.4C1—N1—H1D109.5
H1A—C1—H1B108.0H1C—N1—H1D109.5
C1—C2—C2i110.9 (4)C1—N1—H1E109.5
C1—C2—H2A109.5H1C—N1—H1E109.5
C2i—C2—H2A109.5H1D—N1—H1E109.5
N1—C1—C2—C2i178.5 (4)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···Br1ii0.892.503.355 (4)161
N1—H1D···Br10.892.623.425 (4)150
N1—H1E···Br1iii0.892.543.404 (4)164
N1—H1C···Br1iv0.893.323.393 (3)87
N1—H1D···Br1iv0.892.993.393 (3)110
N1—H1E···Br1iv0.893.333.393 (3)86
Symmetry codes: (ii) x+1, y, z+1; (iii) x, y+1/2, z+1/2; (iv) x, y, z+1.
 

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