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In the title compound, C5H5Br2N2+·Br-·0.5H2O, 3-amino-2,6-di­bromo­pyridine is protonated on the amine N atom and this cation is planar, excluding the H atoms attached to N. The organic cation, bromide anion and interstitial water mol­ecule are held together by hydrogen bonding, bromine-bromine interactions and by a special type of electrostatic interaction between aryl bromine and the centroids of two pyridine rings, forming a bridge-like non-covalent bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018793/dn6151sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018793/dn6151Isup2.hkl
Contains datablock I

CCDC reference: 251644

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.032
  • wR factor = 0.079
  • Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br4 .. Br5 .. 3.36 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT417_ALERT_2_C Short Inter D-H..H-D H1' .. H2B .. 2.13 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br4 .. 3.44 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2C .. BR4 .. 3.01 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N1 .. 2.87 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C2 .. N1 .. 3.80 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.86 From the CIF: _reflns_number_total 2189 Count of symmetry unique reflns 1193 Completeness (_total/calc) 183.49% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 996 Fraction of Friedel pairs measured 0.835 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Pflugrath, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; 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 XP in SHELXTL (Bruker, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

'3-ammonium-2,6-dibromopyridine bromide hemihydrate' top
Crystal data top
C5H5Br2N2+·Br·0.5H2OF(000) = 2544
Mr = 341.82Dx = 2.451 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71070 Å
Hall symbol: F 2 -2dCell parameters from 2190 reflections
a = 12.123 (5) Åθ = 0.8–27.9°
b = 48.809 (17) ŵ = 13.01 mm1
c = 6.262 (2) ÅT = 293 K
V = 3705 (2) Å3Chunk, colorless
Z = 160.20 × 0.20 × 0.20 mm
Data collection top
Rigaku AFC8 CCD Mercury
diffractometer
2189 independent reflections
Radiation source: fine-focus sealed tube1569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
Detector resolution: 14.6306 pixels mm-1θmax = 27.9°, θmin = 1.7°
dtintegrate.ref scansh = 1515
Absorption correction: numerical
(WinGx; Farrugia, 1999)
k = 6464
Tmin = 0.074, Tmax = 0.093l = 78
11841 measured reflections
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0104P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max = 0.045
2161 reflectionsΔρmax = 0.52 e Å3
100 parametersΔρmin = 0.91 e Å3
2 restraintsAbsolute structure: Flack (1983), 996 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (3)
Special details top

Experimental. ????

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
Br40.61856 (6)0.225247 (15)0.60301 (11)0.0379 (2)
Br50.48442 (7)0.195369 (14)0.01119 (14)0.0402 (2)
Br10.37299 (6)0.095111 (15)0.32640 (12)0.0383 (2)
O10.75000.25000.1992 (11)0.039 (2)
H1'0.727 (6)0.2369 (11)0.280 (11)0.059*
N20.3683 (4)0.21807 (11)0.4109 (10)0.0358 (16)
H2A0.43750.22280.44020.054*
H2B0.32410.22390.51500.054*
H2C0.34780.22560.28790.054*
N10.4134 (5)0.14773 (11)0.2026 (9)0.0280 (14)
C30.3076 (5)0.17264 (14)0.5491 (11)0.0313 (17)
H30.27190.18090.66350.038*
C20.3088 (5)0.14462 (13)0.5293 (13)0.0337 (17)
H20.27430.13340.62910.040*
C40.3609 (5)0.18846 (13)0.3943 (11)0.0251 (16)
C50.4096 (5)0.17485 (14)0.2250 (11)0.0284 (16)
C10.3634 (6)0.13375 (13)0.3554 (12)0.0289 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br40.0463 (4)0.0285 (4)0.0388 (4)0.0099 (3)0.0019 (4)0.0025 (3)
Br50.0570 (5)0.0313 (4)0.0323 (4)0.0042 (4)0.0121 (4)0.0031 (4)
Br10.0406 (4)0.0239 (4)0.0504 (5)0.0044 (3)0.0104 (4)0.0037 (4)
O10.046 (5)0.047 (5)0.025 (4)0.002 (4)0.0000.000
N20.047 (4)0.029 (4)0.032 (4)0.003 (3)0.010 (3)0.000 (3)
N10.030 (3)0.022 (3)0.031 (3)0.001 (3)0.002 (3)0.001 (3)
C30.029 (4)0.040 (4)0.025 (4)0.007 (3)0.001 (3)0.004 (3)
C20.033 (4)0.030 (4)0.038 (4)0.014 (3)0.005 (4)0.010 (4)
C40.028 (4)0.017 (3)0.030 (4)0.001 (3)0.000 (3)0.001 (3)
C50.023 (3)0.035 (4)0.026 (4)0.008 (3)0.004 (3)0.004 (3)
C10.036 (4)0.021 (3)0.030 (4)0.000 (3)0.004 (3)0.000 (3)
Geometric parameters (Å, º) top
Br5—C51.902 (6)C3—C21.373 (8)
Br1—C11.898 (6)C3—C41.398 (9)
N2—C41.452 (8)C2—C11.380 (10)
N1—C11.323 (9)C4—C51.383 (9)
N1—C51.332 (7)
C1—N1—C5114.9 (6)N1—C5—C4125.0 (6)
C2—C3—C4118.8 (7)N1—C5—Br5115.6 (5)
C3—C2—C1117.4 (7)C4—C5—Br5119.3 (5)
C5—C4—C3117.6 (6)N1—C1—C2126.3 (6)
C5—C4—N2120.5 (6)N1—C1—Br1114.5 (5)
C3—C4—N2121.9 (6)C2—C1—Br1119.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Br40.86 (6)2.48 (5)3.224 (5)144 (7)
N2—H2A···Br40.892.423.282 (6)163
N2—H2B···O1i0.891.942.783 (7)158
N2—H2C···Br4ii0.892.693.376 (6)134
N2—H2C···Br4iii0.893.013.606 (6)126
C2—H2···N1iv0.932.873.795 (9)176
Symmetry codes: (i) x1/2, y, z+1/2; (ii) x+1, y+1/2, z1/2; (iii) x1/2, y, z1/2; (iv) x1/4, y+1/4, z+3/4.
 

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