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ISSN: 2056-9890

4-Hy­droxy­pyridinium hydrogen sulfate

aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 November 2009; accepted 15 November 2009; online 21 November 2009)

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[Xu, Y.-M., Gao, S. & Ng, S. W. (2009a). Acta Cryst. E65, o3146.],b[Xu, Y.-M., Gao, S. & Ng, S. W. (2009b). Acta Cryst. E65, o3147.]).

[Scheme 1]

Experimental

Crystal data
  • C5H6NO+·HSO4

  • Mr = 193.18

  • Monoclinic, P 21 /c

  • 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.898, Tmax = 0.941

  • 7273 measured reflections

  • 1729 independent reflections

  • 1612 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

S1—O1 1.445 (1)
S1—O2 1.551 (2)
S1—O3 1.437 (1)
S1—O4 1.454 (1)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O4i 0.85 (1) 1.77 (1) 2.603 (2) 168 (3)
O5—H5⋯O1 0.85 (1) 1.77 (1) 2.6166 (19) 175 (3)
N1—H1⋯O3ii 0.84 (1) 2.04 (1) 2.8529 (19) 163 (2)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [C5H6NO]+ [HSO4]- at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
4-Hydroxypyridinium hydrogen sulfate top
Crystal data top
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 top
Rigaku R-AXIS RAPID IP
diffractometer
1729 independent reflections
Radiation source: fine-focus sealed tube1612 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scanθmax = 27.4°, θmin = 3.6°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1313
Tmin = 0.898, Tmax = 0.941k = 1313
7273 measured reflectionsl = 88
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098All H-atom parameters refined
S = 1.03 w = 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
Crystal data top
C5H6NO+·HSO4V = 760.28 (8) Å3
Mr = 193.18Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.4541 (7) ŵ = 0.41 mm1
b = 10.7017 (6) ÅT = 293 K
c = 6.8397 (4) Å0.27 × 0.21 × 0.15 mm
β = 96.503 (2)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
1729 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
1612 reflections with I > 2σ(I)
Tmin = 0.898, Tmax = 0.941Rint = 0.017
7273 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0367 restraints
wR(F2) = 0.098All H-atom parameters refined
S = 1.03Δρmax = 0.52 e Å3
1729 reflectionsΔρmin = 0.39 e Å3
137 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C20.1 (3)O5—C3—C4—C5179.79 (17)
N1—C1—C2—C30.1 (3)C2—C3—C4—C50.4 (3)
C1—C2—C3—O5179.94 (17)C1—N1—C5—C40.1 (3)
C1—C2—C3—C40.2 (2)C3—C4—C5—N10.4 (3)
Hydrogen-bond geometry (Å, º) top
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, z1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC5H6NO+·HSO4
Mr193.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.4541 (7), 10.7017 (6), 6.8397 (4)
β (°) 96.503 (2)
V3)760.28 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.27 × 0.21 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.898, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections
7273, 1729, 1612
Rint0.017
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.098, 1.03
No. of reflections1729
No. of parameters137
No. of restraints7
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.52, 0.39

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
S1—O11.445 (1)S1—O31.437 (1)
S1—O21.551 (2)S1—O41.454 (1)
Hydrogen-bond geometry (Å, º) top
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, z1/2; (ii) x+1, y, z.
 

Acknowledgements

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.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationXu, Y.-M., Gao, S. & Ng, S. W. (2009a). Acta Cryst. E65, o3146.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationXu, Y.-M., Gao, S. & Ng, S. W. (2009b). Acta Cryst. E65, o3147.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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