Literature DB >> 25309212

Crystal structure of 2-amino-4-methyl-pyridin-1-ium (2R,3R)-3-carb-oxy-2,3-di-hydroxy-propano-ate monohydrate.

J V Jovita1, S Sathya1, G Usha1, R Vasanthi1, A Ramanand2.   

Abstract

The title mol-ecular salt, C6H9N2 (+)·C4H5O6 (-)·H2O, crystallized with two 2-amino-4-methyl-pyridin-1-ium cations, two l-(+)-tartaric acid monoanions [systematic name: (2R,3R)-3-carb-oxy-2,3-di-hydroxy-propano-ate] and two water mol-ecules in the asymmetric unit. In the crystal, the cations, anions and water mol-ecules are linked via a number of O-H⋯O and N-H⋯O hydrogen bonds, and a C-H⋯O hydrogen bond, forming a three-dimensional structure.

Entities:  

Keywords:  2-amino-4-methyl­pyridin-1-ium; crystal structure; l-(+)-tartaric acid; tartrate

Year:  2014        PMID： 25309212      PMCID： PMC4186070          DOI： 10.1107/S160053681401842X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological activity of pyridinium derivatives, see: Judge & Bever (2006 ▶); Schwid et al. (1997 ▶); Strupp et al. (2004 ▶). For the crystal structure of a related mol­ecular salt involving the 2-amino-4-methyl­pyridin-1-ium cation, see: Hemamalini & Fun (2010 ▶).

Experimental

Crystal data

C6H9N2 +·C4H5O6 −·H2O M = 276.25 Triclinic, a = 7.176 (3) Å b = 9.9359 (18) Å c = 10.716 (2) Å α = 117.528 (5)° β = 104.792 (7)° γ = 91.701 (7)° V = 645.3 (3) Å3 Z = 2 Mo Kα radiation μ = 0.12 mm−1 T = 293 K 0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.971, T max = 0.976 10211 measured reflections 4999 independent reflections 4769 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.088 S = 1.08 4999 reflections 410 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.27 e Å−3 Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681401842X/su2748sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401842X/su2748Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S160053681401842X/su2748Isup3.cml Click here for additional data file. . DOI: 10.1107/S160053681401842X/su2748fig1.tif The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Click here for additional data file. a . DOI: 10.1107/S160053681401842X/su2748fig2.tif A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details). CCDC reference: 1019274 Additional supporting information: crystallographic information; 3D view; checkCIF report
C6H9N2+·C4H5O6−·H2OZ = 2
Mr = 276.25F(000) = 292
Triclinic, P1Dx = 1.422 Mg m−3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.176 (3) ÅCell parameters from 8251 reflections
b = 9.9359 (18) Åθ = 2.3–32.6°
c = 10.716 (2) ŵ = 0.12 mm−1
α = 117.528 (5)°T = 293 K
β = 104.792 (7)°Block, colourless
γ = 91.701 (7)°0.24 × 0.22 × 0.20 mm
V = 645.3 (3) Å3
Bruker APEXII CCD diffractometer4999 independent reflections
Radiation source: fine-focus sealed tube4769 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −8→8
Tmin = 0.971, Tmax = 0.976k = −12→12
10211 measured reflectionsl = −13→13
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088w = 1/[σ2(Fo2) + (0.0479P)2 + 0.1123P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4999 reflectionsΔρmax = 0.27 e Å−3
410 parametersΔρmin = −0.17 e Å−3
3 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.055 (5)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
O10.74569 (19)0.24776 (17)0.32479 (15)0.0425 (4)
O20.8383 (2)0.48800 (17)0.51261 (16)0.0434 (4)
O30.4999 (2)0.52134 (16)0.54862 (17)0.0421 (5)
O40.5543 (2)0.25906 (18)0.58628 (16)0.0402 (4)
O50.09901 (19)0.22642 (16)0.33245 (15)0.0385 (4)
O60.1808 (2)0.2985 (2)0.57363 (17)0.0469 (5)
O70.73206 (18)0.84899 (15)0.69807 (16)0.0366 (4)
O80.8096 (2)1.08215 (17)0.89449 (17)0.0443 (4)
O91.1844 (2)1.09612 (17)0.92901 (15)0.0408 (4)
O101.0198 (2)1.08903 (18)0.65507 (18)0.0440 (5)
O111.3678 (3)1.0395 (2)0.6194 (3)0.0676 (8)
O121.38559 (17)0.86225 (14)0.69019 (15)0.0340 (4)
C130.7165 (2)0.3699 (2)0.42355 (19)0.0302 (5)
C140.5072 (3)0.3760 (2)0.4327 (2)0.0299 (5)
C150.4308 (2)0.2468 (2)0.4546 (2)0.0295 (5)
C160.2212 (2)0.25924 (19)0.4604 (2)0.0298 (5)
C170.8533 (2)0.9703 (2)0.80181 (19)0.0286 (5)
C181.0658 (2)0.9648 (2)0.80165 (19)0.0275 (5)
C191.0873 (2)0.95937 (19)0.66195 (19)0.0290 (5)
C201.2990 (2)0.9559 (2)0.65682 (19)0.0300 (5)
N10.0123 (3)0.3863 (2)−0.09469 (18)0.0368 (5)
N20.0764 (3)0.3843 (2)0.1268 (2)0.0444 (6)
C10.0410 (3)0.4600 (2)0.0521 (2)0.0316 (5)
C20.0344 (3)0.6200 (2)0.1196 (2)0.0355 (5)
C30.0001 (3)0.6933 (2)0.0375 (2)0.0391 (6)
C4−0.0325 (3)0.6082 (3)−0.1162 (2)0.0417 (7)
C5−0.0249 (3)0.4564 (2)−0.1787 (2)0.0397 (6)
C6−0.0012 (5)0.8623 (3)0.1096 (3)0.0639 (9)
N30.4969 (3)0.4655 (2)0.8719 (2)0.0450 (6)
N40.4515 (3)0.6816 (3)0.8476 (3)0.0535 (8)
O1W1.1106 (3)0.58916 (19)0.42444 (17)0.0448 (5)
C70.5351 (4)0.3913 (3)0.9520 (3)0.0528 (8)
C80.5627 (4)0.4668 (3)1.0974 (3)0.0529 (8)
C90.5523 (3)0.6239 (3)1.1678 (2)0.0499 (8)
C100.5161 (3)0.6983 (3)1.0861 (2)0.0426 (6)
C110.4877 (3)0.6164 (2)0.9329 (2)0.0367 (6)
C120.5813 (6)0.7111 (5)1.3315 (3)0.0825 (13)
O2W1.5440 (2)1.04131 (19)1.03282 (18)0.0444 (5)
H30.613 (5)0.565 (4)0.575 (4)0.067 (9)*
H4A0.513 (5)0.170 (4)0.582 (3)0.062 (8)*
H5A−0.057 (6)0.230 (4)0.344 (4)0.098 (12)*
H140.422600.364700.339600.0360*
H150.431500.147500.371200.0350*
H7A0.582 (5)0.862 (4)0.698 (4)0.082 (10)*
H91.300 (4)1.068 (3)0.959 (3)0.055 (7)*
H10A1.091 (4)1.116 (3)0.618 (3)0.053 (7)*
H181.103500.872100.804800.0330*
H191.003900.865900.576500.0350*
H20.053700.675400.220700.0430*
H2NA0.085 (3)0.429 (3)0.217 (3)0.029 (5)*
H4−0.058900.65630−0.173800.0500*
H2NB0.071 (5)0.290 (4)0.081 (3)0.058 (8)*
H5−0.045400.39950−0.279900.0480*
H6A0.093300.911800.088000.0960*
H6B0.031400.903200.214600.0960*
H6C−0.129000.880700.072900.0960*
H290.015 (4)0.299 (3)−0.138 (3)0.047 (7)*
H3N0.481 (4)0.412 (3)0.781 (3)0.048 (7)*
H70.542300.286900.905500.0630*
H4NA0.441 (4)0.624 (3)0.754 (3)0.045 (7)*
H80.588900.415201.151700.0630*
H4NB0.452 (5)0.776 (4)0.890 (4)0.068 (10)*
H100.510300.802901.131800.0510*
H12A0.704700.699401.383400.1240*
H12B0.477700.671101.353300.1240*
H12C0.579800.818301.362100.1240*
H1WA1.033 (4)0.554 (3)0.457 (3)0.052 (7)*
H1WB1.211 (5)0.620 (3)0.487 (3)0.055 (8)*
H2WA1.617 (5)1.059 (4)0.992 (3)0.062 (9)*
H2WB1.591 (4)1.099 (3)1.125 (4)0.051 (7)*
U11U22U33U12U13U23
O10.0253 (6)0.0529 (9)0.0359 (7)0.0069 (6)0.0113 (5)0.0098 (7)
O20.0303 (7)0.0451 (8)0.0468 (8)−0.0004 (6)0.0125 (6)0.0160 (7)
O30.0397 (8)0.0312 (7)0.0588 (9)0.0085 (6)0.0267 (7)0.0185 (7)
O40.0343 (7)0.0467 (8)0.0487 (8)0.0063 (6)0.0085 (6)0.0326 (7)
O50.0257 (6)0.0419 (7)0.0344 (7)0.0021 (5)0.0100 (5)0.0076 (6)
O60.0457 (8)0.0691 (10)0.0530 (9)0.0287 (8)0.0309 (7)0.0421 (8)
O70.0240 (6)0.0291 (6)0.0471 (8)0.0044 (5)0.0135 (5)0.0095 (6)
O80.0300 (7)0.0367 (7)0.0509 (8)0.0049 (6)0.0193 (6)0.0056 (6)
O90.0262 (6)0.0410 (7)0.0380 (7)0.0055 (6)0.0055 (5)0.0076 (6)
O100.0455 (8)0.0532 (9)0.0648 (9)0.0284 (7)0.0330 (8)0.0444 (8)
O110.0513 (9)0.0784 (12)0.1307 (18)0.0294 (9)0.0552 (11)0.0819 (13)
O120.0245 (6)0.0340 (7)0.0484 (7)0.0084 (5)0.0153 (5)0.0215 (6)
C130.0263 (8)0.0413 (10)0.0292 (8)0.0072 (8)0.0106 (7)0.0209 (8)
C140.0258 (8)0.0355 (9)0.0334 (9)0.0074 (7)0.0111 (7)0.0196 (7)
C150.0262 (8)0.0291 (8)0.0336 (9)0.0057 (7)0.0115 (7)0.0142 (7)
C160.0286 (9)0.0254 (8)0.0402 (9)0.0063 (7)0.0156 (7)0.0170 (7)
C170.0255 (8)0.0306 (9)0.0342 (9)0.0070 (7)0.0123 (7)0.0176 (7)
C180.0233 (8)0.0249 (8)0.0357 (9)0.0063 (6)0.0106 (7)0.0150 (7)
C190.0242 (8)0.0291 (9)0.0362 (9)0.0073 (7)0.0117 (7)0.0164 (8)
C200.0286 (8)0.0274 (8)0.0360 (9)0.0053 (7)0.0153 (7)0.0141 (7)
N10.0436 (9)0.0281 (8)0.0353 (8)0.0098 (7)0.0149 (7)0.0109 (7)
N20.0646 (12)0.0312 (9)0.0364 (10)0.0133 (8)0.0164 (8)0.0149 (8)
C10.0290 (8)0.0311 (9)0.0334 (9)0.0063 (7)0.0106 (7)0.0140 (8)
C20.0381 (10)0.0292 (9)0.0329 (9)0.0061 (7)0.0124 (8)0.0093 (8)
C30.0349 (10)0.0307 (10)0.0507 (11)0.0032 (8)0.0128 (9)0.0193 (9)
C40.0407 (11)0.0459 (12)0.0473 (11)0.0082 (9)0.0135 (9)0.0295 (10)
C50.0385 (10)0.0480 (12)0.0335 (9)0.0073 (8)0.0123 (8)0.0198 (9)
C60.0813 (19)0.0347 (12)0.0725 (17)0.0119 (12)0.0208 (15)0.0248 (12)
N30.0541 (11)0.0444 (10)0.0342 (9)0.0062 (8)0.0122 (8)0.0179 (8)
N40.0698 (14)0.0596 (13)0.0480 (12)0.0180 (11)0.0234 (10)0.0365 (11)
O1W0.0442 (8)0.0447 (8)0.0366 (8)−0.0045 (7)0.0102 (7)0.0143 (7)
C70.0550 (13)0.0454 (12)0.0626 (15)0.0048 (10)0.0142 (11)0.0320 (12)
C80.0500 (13)0.0651 (15)0.0577 (14)0.0048 (11)0.0122 (11)0.0435 (13)
C90.0369 (11)0.0773 (17)0.0395 (11)0.0048 (11)0.0085 (9)0.0334 (12)
C100.0403 (11)0.0472 (12)0.0404 (10)0.0109 (9)0.0156 (9)0.0194 (9)
C110.0319 (9)0.0461 (11)0.0376 (10)0.0063 (8)0.0126 (7)0.0238 (9)
C120.092 (2)0.108 (3)0.0447 (14)0.019 (2)0.0205 (15)0.0349 (16)
O2W0.0345 (7)0.0524 (9)0.0328 (8)0.0026 (6)0.0055 (6)0.0125 (7)
O1—C131.256 (2)C2—C31.363 (3)
O2—C131.237 (3)N2—H2NA0.84 (3)
O3—C141.418 (3)N2—H2NB0.83 (4)
O4—C151.410 (2)C3—C41.410 (3)
O5—C161.308 (2)C3—C61.491 (4)
O6—C161.207 (2)C4—C51.348 (4)
O3—H30.82 (4)C2—H20.9300
O4—H4A0.90 (4)N3—C111.342 (3)
O5—H5A1.16 (4)N3—C71.354 (4)
O7—C171.285 (2)N4—C111.326 (4)
O8—C171.216 (3)C4—H40.9300
O9—C181.409 (2)C5—H50.9300
O10—C191.417 (3)C6—H6A0.9600
O11—C201.216 (3)C6—H6B0.9600
O12—C201.268 (3)C6—H6C0.9600
C13—C141.531 (3)N3—H3N0.84 (3)
C14—C151.519 (3)N4—H4NB0.83 (4)
C15—C161.527 (2)N4—H4NA0.88 (3)
O7—H7A1.09 (4)C7—C81.335 (4)
O9—H90.91 (3)C8—C91.399 (4)
O10—H10A0.83 (3)C9—C101.369 (4)
C14—H140.9800C9—C121.506 (3)
C15—H150.9800C10—C111.408 (3)
C17—C181.528 (2)O1W—H1WB0.78 (3)
C18—C191.520 (3)O1W—H1WA0.87 (3)
C19—C201.535 (2)C7—H70.9300
N1—C51.355 (3)C8—H80.9300
N1—C11.347 (3)C10—H100.9300
N2—C11.317 (3)C12—H12C0.9600
C18—H180.9800C12—H12A0.9600
C19—H190.9800C12—H12B0.9600
C1—C21.418 (3)O2W—H2WA0.82 (4)
N1—H290.78 (3)O2W—H2WB0.84 (4)
C14—O3—H3100 (3)C1—N2—H2NB119 (2)
C15—O4—H4A103.0 (19)C1—C2—C3120.58 (17)
C16—O5—H5A108.0 (18)H2NA—N2—H2NB121 (3)
O1—C13—C14116.99 (16)C2—C3—C4119.4 (2)
O1—C13—O2126.88 (16)C4—C3—C6120.2 (2)
O2—C13—C14116.10 (17)C2—C3—C6120.37 (19)
O3—C14—C13109.65 (16)C3—C4—C5119.3 (2)
O3—C14—C15110.52 (16)N1—C5—C4120.27 (18)
C13—C14—C15111.91 (17)C1—C2—H2120.00
C14—C15—C16108.80 (17)C3—C2—H2120.00
O4—C15—C14108.89 (16)C7—N3—C11122.6 (2)
O4—C15—C16111.36 (15)C5—C4—H4120.00
O5—C16—O6126.04 (16)C3—C4—H4120.00
O5—C16—C15112.27 (15)N1—C5—H5120.00
O6—C16—C15121.67 (16)C4—C5—H5120.00
C17—O7—H7A111 (2)C3—C6—H6B109.00
C18—O9—H9107.2 (19)C3—C6—H6C109.00
C19—O10—H10A106 (2)C3—C6—H6A109.00
O3—C14—H14108.00H6A—C6—H6C110.00
C13—C14—H14108.00H6B—C6—H6C109.00
C15—C14—H14108.00H6A—C6—H6B109.00
C16—C15—H15109.00C11—N3—H3N121 (2)
O4—C15—H15109.00C7—N3—H3N116 (2)
C14—C15—H15109.00C11—N4—H4NA118 (2)
O7—C17—C18114.13 (16)H4NA—N4—H4NB126 (3)
O7—C17—O8125.05 (16)C11—N4—H4NB116 (3)
O8—C17—C18120.83 (17)N3—C7—C8120.5 (3)
O9—C18—C17108.17 (14)C7—C8—C9119.9 (3)
O9—C18—C19111.32 (16)C8—C9—C12120.8 (3)
C17—C18—C19109.84 (14)C10—C9—C12120.1 (3)
C18—C19—C20112.12 (14)C8—C9—C10119.2 (2)
O10—C19—C18108.04 (15)C9—C10—C11120.0 (2)
O10—C19—C20111.07 (16)N3—C11—C10117.8 (2)
O11—C20—O12125.81 (18)N4—C11—C10122.9 (2)
O11—C20—C19118.3 (2)N3—C11—N4119.2 (2)
O12—C20—C19115.93 (17)H1WA—O1W—H1WB105 (3)
C1—N1—C5123.5 (2)N3—C7—H7120.00
C17—C18—H18109.00C8—C7—H7120.00
C19—C18—H18109.00C9—C8—H8120.00
O9—C18—H18109.00C7—C8—H8120.00
C18—C19—H19109.00C9—C10—H10120.00
C20—C19—H19108.00C11—C10—H10120.00
O10—C19—H19109.00C9—C12—H12B109.00
N1—C1—N2120.2 (2)C9—C12—H12C109.00
N1—C1—C2116.89 (19)C9—C12—H12A109.00
N2—C1—C2122.93 (18)H12A—C12—H12C110.00
C5—N1—H29115 (2)H12B—C12—H12C109.00
C1—N1—H29122 (2)H12A—C12—H12B109.00
C1—N2—H2NA120 (2)H2WA—O2W—H2WB109 (3)
O1—C13—C14—O3−179.57 (18)C18—C19—C20—O11−135.1 (2)
O1—C13—C14—C1557.4 (2)C18—C19—C20—O1246.2 (2)
O2—C13—C14—O3−1.2 (3)C5—N1—C1—N2180.0 (2)
O2—C13—C14—C15−124.3 (2)C5—N1—C1—C2−1.1 (3)
O3—C14—C15—O4−63.3 (2)C1—N1—C5—C40.9 (4)
O3—C14—C15—C1658.3 (2)N2—C1—C2—C3179.0 (2)
C13—C14—C15—O459.26 (19)N1—C1—C2—C30.1 (3)
C13—C14—C15—C16−179.20 (14)C1—C2—C3—C41.2 (3)
O4—C15—C16—O5−170.89 (18)C1—C2—C3—C6−178.3 (2)
O4—C15—C16—O610.5 (3)C6—C3—C4—C5178.0 (2)
C14—C15—C16—O569.1 (2)C2—C3—C4—C5−1.4 (3)
C14—C15—C16—O6−109.5 (2)C3—C4—C5—N10.5 (3)
O7—C17—C18—O9−173.74 (17)C11—N3—C7—C81.0 (4)
O7—C17—C18—C1964.6 (2)C7—N3—C11—N4179.3 (2)
O8—C17—C18—O96.1 (3)C7—N3—C11—C10−1.1 (4)
O8—C17—C18—C19−115.6 (2)N3—C7—C8—C9−0.1 (4)
O9—C18—C19—O10−63.25 (18)C7—C8—C9—C12179.5 (3)
O9—C18—C19—C2059.5 (2)C7—C8—C9—C10−0.8 (4)
C17—C18—C19—O1056.5 (2)C8—C9—C10—C110.7 (3)
C17—C18—C19—C20179.23 (17)C12—C9—C10—C11−179.6 (3)
O10—C19—C20—O11−14.1 (3)C9—C10—C11—N4179.8 (2)
O10—C19—C20—O12167.13 (16)C9—C10—C11—N30.2 (3)
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O20.87 (3)1.86 (3)2.725 (3)172 (3)
O1W—H1WB···O3i0.78 (3)2.39 (4)3.012 (3)137 (3)
O1W—H1WB···O120.78 (3)2.39 (3)3.006 (3)137 (3)
O3—H3···O20.82 (4)1.95 (4)2.562 (2)131 (4)
O3—H3···O70.82 (4)2.51 (4)3.072 (3)127 (3)
N2—H2NA···O1Wii0.84 (3)2.00 (3)2.819 (3)164 (3)
N3—H3N···O40.84 (3)2.15 (3)2.939 (3)157 (3)
N3—H3N···O60.84 (3)2.44 (3)3.047 (3)130 (3)
N2—H2NB···O8iii0.83 (4)2.41 (3)3.032 (3)132 (3)
N2—H2NB···O9iii0.83 (4)2.21 (4)2.942 (3)147 (3)
O4—H4A···O11iv0.90 (4)1.88 (4)2.732 (3)156 (3)
O2W—H2WA···O8i0.82 (4)2.00 (4)2.819 (3)173 (4)
O5—H5A···O1ii1.16 (4)1.41 (4)2.534 (2)163 (4)
N4—H4NA···O30.88 (3)2.12 (3)2.968 (3)163 (3)
O7—H7A···O12ii1.09 (4)1.39 (4)2.476 (2)174 (4)
N4—H4NB···O2Wii0.83 (4)2.32 (4)3.128 (4)164 (3)
N4—H4NB···O12ii0.83 (4)2.60 (4)2.955 (4)108 (3)
O9—H9···O2W0.91 (3)1.81 (3)2.715 (3)172 (3)
O10—H10A···O6v0.83 (3)2.19 (3)2.912 (3)145 (3)
O10—H10A···O110.83 (3)2.15 (3)2.648 (3)119 (3)
N1—H29···O10iii0.78 (3)2.24 (3)2.946 (3)151 (3)
C5—H5···O6vi0.932.463.158 (3)132
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1W—H1WA⋯O20.87 (3)1.86 (3)2.725 (3)172 (3)
O1W—H1WB⋯O3i 0.78 (3)2.39 (4)3.012 (3)137 (3)
O1W—H1WB⋯O120.78 (3)2.39 (3)3.006 (3)137 (3)
O3—H3⋯O20.82 (4)1.95 (4)2.562 (2)131 (4)
O3—H3⋯O70.82 (4)2.51 (4)3.072 (3)127 (3)
N2—H2NA⋯O1W ii 0.84 (3)2.00 (3)2.819 (3)164 (3)
N3—H3N⋯O40.84 (3)2.15 (3)2.939 (3)157 (3)
N3—H3N⋯O60.84 (3)2.44 (3)3.047 (3)130 (3)
N2—H2NB⋯O8iii 0.83 (4)2.41 (3)3.032 (3)132 (3)
N2—H2NB⋯O9iii 0.83 (4)2.21 (4)2.942 (3)147 (3)
O4—H4A⋯O11iv 0.90 (4)1.88 (4)2.732 (3)156 (3)
O2W—H2WA⋯O8i 0.82 (4)2.00 (4)2.819 (3)173 (4)
O5—H5A⋯O1ii 1.16 (4)1.41 (4)2.534 (2)163 (4)
N4—H4NA⋯O30.88 (3)2.12 (3)2.968 (3)163 (3)
O7—H7A⋯O12ii 1.09 (4)1.39 (4)2.476 (2)174 (4)
N4—H4NB⋯O2W ii 0.83 (4)2.32 (4)3.128 (4)164 (3)
N4—H4NB⋯O12ii 0.83 (4)2.60 (4)2.955 (4)108 (3)
O9—H9⋯O2W 0.91 (3)1.81 (3)2.715 (3)172 (3)
O10—H10A⋯O6v 0.83 (3)2.19 (3)2.912 (3)145 (3)
O10—H10A⋯O110.83 (3)2.15 (3)2.648 (3)119 (3)
N1—H29⋯O10iii 0.78 (3)2.24 (3)2.946 (3)151 (3)
C5—H5⋯O6vi 0.932.463.158 (3)132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  5 in total

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Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  S R Schwid; M D Petrie; M P McDermott; D S Tierney; D H Mason; A D Goodman
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Journal:  Neurology       Date:  2004-05-11       Impact factor: 9.910

Review 4.  Potassium channel blockers in multiple sclerosis: neuronal Kv channels and effects of symptomatic treatment.

Authors:  Susan I V Judge; Christopher T Bever
Journal:  Pharmacol Ther       Date:  2006-02-09       Impact factor: 12.310

5.  2-Amino-4-methyl-pyridinium 2-hy-droxy-benzoate.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-31
  5 in total

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