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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3148.
Published online 2009 November 21. doi:  10.1107/S1600536809048533
PMCID: PMC2971937

4-Hydroxy­pyridinium hydrogen sulfate

Abstract

The crystal structure of the title salt, C5H6NO+·HSO4 , consists of planar(r.m.s. deviation = 0.001 Å) 4-hydroxy­pyridinium cations and hydrogen sulfate anions which are hydrogen bonded into a layer motif. In the anion, the S—O bond [1.551 (2) Å] involving the O atom bearing the acid H atom is longer than the other three S—O bonds, which range from 1.437 (1) to 1.454 (1) Å.

Related literature

For the crystal structures of bis­(4-hydroxy­pyridinium) sulfate monohydrate and tris­(4-hydroxy­pyridinium) hydrogen disulfate monohydrate, see: Xu et al. (2009a [triangle],b [triangle]).

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Object name is e-65-o3148-scheme1.jpg

Experimental

Crystal data

  • C5H6NO+·HSO4
  • M r = 193.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3148-efi1.jpg
  • a = 10.4541 (7) Å
  • b = 10.7017 (6) Å
  • c = 6.8397 (4) Å
  • β = 96.503 (2)°
  • V = 760.28 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 293 K
  • 0.27 × 0.21 × 0.15 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.898, T max = 0.941
  • 7273 measured reflections
  • 1729 independent reflections
  • 1612 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.098
  • S = 1.03
  • 1729 reflections
  • 137 parameters
  • 7 restraints
  • All H-atom parameters refined
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048533/xu2677sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048533/xu2677Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The compound is a side product that was obtained when commercially available 4-hydroxypyridine-3-sulfonic acid was recrystallized from water. Its crystals were obtained from a water solution.

Refinement

Carbon-bound H-atoms refined with a C–H distance restraint of 0.95±0.01 Å; their temperature factors were refined. The nitrogen- and oxygen-bound H-atoms were refined with a distance restraint of N–H = O–H = 0.85±0.01 Å; their temperature factors were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [C5H6NO]+ [HSO4]- at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C5H6NO+·HSO4F(000) = 400
Mr = 193.18Dx = 1.688 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6627 reflections
a = 10.4541 (7) Åθ = 3.6–27.4°
b = 10.7017 (6) ŵ = 0.41 mm1
c = 6.8397 (4) ÅT = 293 K
β = 96.503 (2)°Prism, colorless
V = 760.28 (8) Å30.27 × 0.21 × 0.15 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP diffractometer1729 independent reflections
Radiation source: fine-focus sealed tube1612 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scanθmax = 27.4°, θmin = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −13→13
Tmin = 0.898, Tmax = 0.941k = −13→13
7273 measured reflectionsl = −8→8

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098All H-atom parameters refined
S = 1.03w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3712P] where P = (Fo2 + 2Fc2)/3
1729 reflections(Δ/σ)max = 0.001
137 parametersΔρmax = 0.52 e Å3
7 restraintsΔρmin = −0.39 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.15352 (4)0.36664 (3)0.22053 (6)0.02984 (15)
O10.28767 (13)0.37320 (14)0.2986 (3)0.0580 (4)
O20.1438 (2)0.41518 (14)0.0056 (2)0.0657 (5)
O30.07735 (11)0.45271 (12)0.3196 (2)0.0423 (3)
O40.10415 (14)0.23950 (12)0.21136 (18)0.0430 (3)
O50.46894 (12)0.20467 (13)0.2977 (2)0.0486 (4)
N10.82340 (14)0.36324 (15)0.3509 (2)0.0416 (4)
C10.72047 (18)0.43863 (17)0.3364 (3)0.0388 (4)
C20.59869 (16)0.39037 (16)0.3180 (3)0.0351 (4)
C30.58308 (15)0.26042 (15)0.3148 (2)0.0320 (3)
C40.69235 (16)0.18433 (16)0.3312 (3)0.0359 (4)
C50.81115 (16)0.23848 (19)0.3484 (3)0.0410 (4)
H10.8975 (14)0.395 (2)0.366 (4)0.063 (7)*
H20.134 (3)0.357 (2)−0.078 (4)0.079 (9)*
H50.412 (2)0.2615 (19)0.293 (4)0.063 (7)*
H1A0.735 (2)0.5257 (10)0.338 (3)0.044 (6)*
H2A0.5283 (16)0.4452 (18)0.302 (3)0.049 (6)*
H40.6824 (19)0.0967 (9)0.330 (3)0.040 (5)*
H5A0.8881 (16)0.191 (2)0.356 (4)0.061 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0273 (2)0.0272 (2)0.0352 (2)−0.00275 (13)0.00428 (15)−0.00138 (13)
O10.0264 (7)0.0495 (9)0.0963 (12)0.0041 (5)−0.0012 (7)−0.0159 (8)
O20.1253 (16)0.0347 (7)0.0384 (7)−0.0135 (9)0.0154 (8)0.0017 (6)
O30.0312 (6)0.0428 (7)0.0538 (8)0.0005 (5)0.0090 (5)−0.0101 (6)
O40.0581 (8)0.0317 (6)0.0391 (6)−0.0130 (5)0.0045 (5)0.0004 (5)
O50.0254 (6)0.0346 (7)0.0852 (11)−0.0021 (5)0.0041 (6)−0.0049 (6)
N10.0289 (7)0.0507 (9)0.0457 (8)−0.0105 (6)0.0064 (6)−0.0084 (7)
C10.0439 (9)0.0337 (8)0.0397 (9)−0.0068 (7)0.0086 (7)−0.0045 (7)
C20.0329 (8)0.0303 (8)0.0424 (9)0.0037 (6)0.0052 (7)−0.0022 (6)
C30.0268 (7)0.0316 (8)0.0376 (8)−0.0003 (6)0.0037 (6)−0.0026 (6)
C40.0315 (8)0.0308 (8)0.0454 (9)0.0034 (6)0.0037 (7)−0.0031 (7)
C50.0279 (8)0.0485 (10)0.0466 (9)0.0043 (7)0.0040 (7)−0.0058 (8)

Geometric parameters (Å, °)

S1—O11.445 (1)N1—H10.841 (10)
S1—O21.551 (2)C1—C21.366 (2)
S1—O31.437 (1)C1—H1A0.945 (10)
S1—O41.454 (1)C2—C31.400 (2)
S1—O21.5514 (15)C2—H2A0.938 (10)
O2—H20.848 (10)C3—C41.397 (2)
O5—C31.3273 (19)C4—C51.363 (2)
O5—H50.849 (10)C4—H40.943 (9)
N1—C11.340 (2)C5—H5A0.947 (10)
N1—C51.341 (3)
O3—S1—O1111.16 (8)C2—C1—H1A121.6 (13)
O3—S1—O4114.04 (8)C1—C2—C3118.86 (16)
O1—S1—O4112.73 (9)C1—C2—H2A119.0 (14)
O3—S1—O2104.60 (9)C3—C2—H2A122.1 (14)
O1—S1—O2106.91 (11)O5—C3—C4117.63 (15)
O4—S1—O2106.71 (8)O5—C3—C2123.36 (15)
S1—O2—H2113 (2)C4—C3—C2119.01 (15)
C3—O5—H5107.5 (19)C5—C4—C3119.20 (16)
C1—N1—C5121.59 (15)C5—C4—H4121.5 (12)
C1—N1—H1119.2 (19)C3—C4—H4119.3 (12)
C5—N1—H1119 (2)N1—C5—C4120.59 (16)
N1—C1—C2120.75 (16)N1—C5—H5A116.9 (16)
N1—C1—H1A117.6 (13)C4—C5—H5A122.5 (16)
C5—N1—C1—C2−0.1 (3)O5—C3—C4—C5179.79 (17)
N1—C1—C2—C30.1 (3)C2—C3—C4—C5−0.4 (3)
C1—C2—C3—O5179.94 (17)C1—N1—C5—C4−0.1 (3)
C1—C2—C3—C40.2 (2)C3—C4—C5—N10.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.85 (1)1.77 (1)2.603 (2)168 (3)
O5—H5···O10.85 (1)1.77 (1)2.6166 (19)175 (3)
N1—H1···O3ii0.84 (1)2.04 (1)2.8529 (19)163 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2677).

References

  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.
  • Xu, Y.-M., Gao, S. & Ng, S. W. (2009a). Acta Cryst. E65, o3146. [PMC free article] [PubMed]
  • Xu, Y.-M., Gao, S. & Ng, S. W. (2009b). Acta Cryst. E65, o3147. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography