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In the title compound, [C5H6N3]Br·H2O, the 2,6-di­amino­pyridine is protonated on the ring N atom. The cation is planar. The moieties are held together by extensive hydrogen bonding and by π–π interactions. The bromide ion is hydrogen bonded, as acceptor, to two H2O mol­ecules, with an average Br...H—O(H2O) distance of 3.322 (11) Å, to the ring N atom Br...N—H(NH) 3.353 (3) Å, and to four amino N atoms, with an average Br...H—N(NH2) 3.63 (14) Å. The water mol­ecule bonds, as acceptor, to the pyridine N atom O...H—N(NH2) 2.583 (5) Å. The closest π–π interaction is between pyridine ring planes, with an interplanar spacing 3.358 Å apart.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019111/br6115sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019111/br6115Isup2.hkl
Contains datablock I

CCDC reference: 225701

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.038
  • wR factor = 0.100
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low .............. 24.97 Deg.
Alert level B PLAT415_ALERT_2_B Short Inter D-H..H-X H2A .. H5A = 1.98 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C2 = 5.41 su PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ? PLAT731_ALERT_1_C Bond Calc 0.88(4), Rep 0.882(19) ...... 2.11 su-Rat O -H1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.88(5), Rep 0.881(19) ...... 2.63 su-Rat O -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(4), Rep 0.882(19) ...... 2.11 su-Rat O -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(5), Rep 0.881(19) ...... 2.63 su-Rat O -H2 1.555 1.555
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, 1996b); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: XS in SHELXTL (Bruker, 1996); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.

'2,6-Diaminopyridinium Bromide Hydrate' top
Crystal data top
C5H8N3+·Br·H2OZ = 2
Mr = 208.07F(000) = 208
Triclinic, P1Dx = 1.722 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1225 (12) ÅCell parameters from 28 reflections
b = 7.2333 (8) Åθ = 5.9–18.1°
c = 8.7082 (13) ŵ = 5.06 mm1
α = 91.557 (11)°T = 295 K
β = 102.518 (17)°Parallelpiped, pink
γ = 112.627 (11)°0.40 × 0.35 × 0.28 mm
V = 401.21 (10) Å3
Data collection top
Siemens P21 upgraded to P4
diffractometer
1292 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω scansh = 81
Absorption correction: psi-scan
(XPREP in SHELXTL; Bruker, 1996)
k = 88
Tmin = 0.146, Tmax = 0.242l = 1010
1781 measured reflections3 standard reflections every 97 reflections
1412 independent reflections intensity decay: <0.01%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0593P)2 + 0.2936P]
where P = (Fo2 + 2Fc2)/3
1412 reflections(Δ/σ)max < 0.001
99 parametersΔρmax = 0.44 e Å3
3 restraintsΔρmin = 0.63 e Å3
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
C50.6409 (6)0.7561 (6)0.0186 (5)0.0486 (9)
H5A0.75670.75810.05260.058*
Br0.88031 (6)0.66391 (6)0.63033 (4)0.0519 (2)
N20.1227 (4)0.7448 (5)0.1128 (4)0.0430 (7)
H2A0.01170.71020.03660.052*
H2B0.11840.77420.20790.052*
N10.2839 (5)0.7032 (5)0.0697 (4)0.0431 (7)
H1A0.16420.67090.13580.052*
C20.2996 (6)0.7528 (6)0.0837 (5)0.0455 (9)
N60.4118 (6)0.6507 (6)0.2809 (4)0.0597 (9)
H6A0.28920.62040.34230.072*
H6B0.51230.64840.31960.072*
C30.4874 (6)0.8053 (6)0.1924 (5)0.0501 (9)
H3A0.50090.83890.29930.060*
C60.4459 (6)0.7013 (6)0.1262 (5)0.0443 (8)
C40.6576 (6)0.8066 (6)0.1377 (5)0.0531 (10)
H4A0.78680.84300.20970.064*
O0.1830 (6)0.9045 (6)0.3976 (4)0.0673 (8)
H10.177 (8)1.024 (4)0.404 (6)0.075 (17)*
H20.130 (9)0.834 (7)0.470 (6)0.088 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C50.039 (2)0.049 (2)0.061 (3)0.0188 (17)0.0152 (17)0.0046 (18)
Br0.0481 (3)0.0676 (3)0.0451 (3)0.0279 (2)0.01310 (18)0.00455 (18)
N20.0290 (15)0.0647 (19)0.0409 (17)0.0226 (14)0.0123 (12)0.0068 (14)
N10.0327 (15)0.0492 (17)0.0483 (18)0.0184 (13)0.0080 (13)0.0059 (14)
C20.043 (2)0.0476 (19)0.051 (2)0.0209 (17)0.0173 (17)0.0097 (17)
N60.055 (2)0.084 (3)0.047 (2)0.036 (2)0.0118 (16)0.0010 (18)
C30.048 (2)0.058 (2)0.045 (2)0.0234 (19)0.0086 (17)0.0026 (17)
C60.044 (2)0.0431 (18)0.051 (2)0.0212 (16)0.0156 (17)0.0088 (16)
C40.039 (2)0.056 (2)0.059 (3)0.0187 (18)0.0032 (18)0.0000 (19)
O0.078 (2)0.077 (2)0.064 (2)0.0399 (19)0.0344 (17)0.0142 (17)
Geometric parameters (Å, º) top
C5—C41.367 (6)C2—C31.368 (6)
C5—C61.399 (6)N6—C61.331 (5)
C5—H5A0.9300N6—H6A0.8600
N2—C21.319 (5)N6—H6B0.8600
N2—H2A0.8600C3—C41.392 (6)
N2—H2B0.8600C3—H3A0.9300
N1—C21.343 (5)C4—H4A0.9300
N1—C61.353 (5)O—H10.882 (19)
N1—H1A0.8600O—H20.881 (19)
C4—C5—C6118.6 (4)C6—N6—H6B120.0
C4—C5—H5A120.7H6A—N6—H6B120.0
C6—C5—H5A120.7C2—C3—C4117.7 (4)
C2—N2—H2A120.0C2—C3—H3A121.2
C2—N2—H2B120.0C4—C3—H3A121.2
H2A—N2—H2B120.0N6—C6—N1118.3 (4)
C2—N1—C6123.7 (3)N6—C6—C5123.7 (4)
C2—N1—H1A118.2N1—C6—C5117.9 (4)
C6—N1—H1A118.2C5—C4—C3122.2 (4)
N2—C2—N1113.7 (3)C5—C4—H4A118.9
N2—C2—C3126.4 (4)C3—C4—H4A118.9
N1—C2—C3120.0 (4)H1—O—H2110 (3)
C6—N6—H6A120.0
C6—N1—C2—N2180.0 (3)C2—N1—C6—C50.7 (6)
C6—N1—C2—C30.1 (6)C4—C5—C6—N6179.5 (4)
N2—C2—C3—C4179.3 (4)C4—C5—C6—N10.7 (6)
N1—C2—C3—C40.6 (6)C6—C5—C4—C30.1 (6)
C2—N1—C6—N6179.6 (4)C2—C3—C4—C50.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O0.861.762.583 (5)161
N1—H1A···Bri0.862.523.353 (3)162
N6—H6A···Brii0.862.913.464 (4)124
N6—H6A···Bri0.863.013.735 (4)144
N6—H6B···Briii0.862.713.553 (4)167
O—H1···Briv0.88 (2)2.46 (2)3.329 (4)169 (5)
O—H2···Brv0.88 (2)2.47 (3)3.314 (4)161 (5)
N2—H2B···Brvi0.863.513.752 (3)100
Symmetry codes: (i) x1, y, z1; (ii) x+1, y+1, z; (iii) x, y, z1; (iv) x+1, y+2, z+1; (v) x1, y, z; (vi) x+1, y+1, z+1.
 

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