4-Hydroxy-pyridinium hydrogen sulfate.

The crystal structure of the title salt, C(5)H(6)NO(+)·HSO(4) (-), consists of planar(r.m.s. deviation = 0.001 Å) 4-hydroxy-pyridinium 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 ▶,b ▶).

Experimental

Crystal data

C5H6NO+·HSO4 −

M = 193.18

Monoclinic,

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 ▶) 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 ▶); cell refinement: RAPID-AUTO; 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 ▶).

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

C5H6NO+·HSO4−	F(000) = 400
Mr = 193.18	Dx = 1.688 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6627 reflections
a = 10.4541 (7) Å	θ = 3.6–27.4°
b = 10.7017 (6) Å	µ = 0.41 mm−1
c = 6.8397 (4) Å	T = 293 K
β = 96.503 (2)°	Prism, colorless
V = 760.28 (8) Å3	0.27 × 0.21 × 0.15 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	1729 independent reflections
Radiation source: fine-focus sealed tube	1612 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scan	θmax = 27.4°, θmin = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.898, Tmax = 0.941	k = −13→13
7273 measured reflections	l = −8→8

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	All 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 parameters	Δρmax = 0.52 e Å−3
7 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.15352 (4)	0.36664 (3)	0.22053 (6)	0.02984 (15)
O1	0.28767 (13)	0.37320 (14)	0.2986 (3)	0.0580 (4)
O2	0.1438 (2)	0.41518 (14)	0.0056 (2)	0.0657 (5)
O3	0.07735 (11)	0.45271 (12)	0.3196 (2)	0.0423 (3)
O4	0.10415 (14)	0.23950 (12)	0.21136 (18)	0.0430 (3)
O5	0.46894 (12)	0.20467 (13)	0.2977 (2)	0.0486 (4)
N1	0.82340 (14)	0.36324 (15)	0.3509 (2)	0.0416 (4)
C1	0.72047 (18)	0.43863 (17)	0.3364 (3)	0.0388 (4)
C2	0.59869 (16)	0.39037 (16)	0.3180 (3)	0.0351 (4)
C3	0.58308 (15)	0.26042 (15)	0.3148 (2)	0.0320 (3)
C4	0.69235 (16)	0.18433 (16)	0.3312 (3)	0.0359 (4)
C5	0.81115 (16)	0.23848 (19)	0.3484 (3)	0.0410 (4)
H1	0.8975 (14)	0.395 (2)	0.366 (4)	0.063 (7)*
H2	0.134 (3)	0.357 (2)	−0.078 (4)	0.079 (9)*
H5	0.412 (2)	0.2615 (19)	0.293 (4)	0.063 (7)*
H1A	0.735 (2)	0.5257 (10)	0.338 (3)	0.044 (6)*
H2A	0.5283 (16)	0.4452 (18)	0.302 (3)	0.049 (6)*
H4	0.6824 (19)	0.0967 (9)	0.330 (3)	0.040 (5)*
H5A	0.8881 (16)	0.191 (2)	0.356 (4)	0.061 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0273 (2)	0.0272 (2)	0.0352 (2)	−0.00275 (13)	0.00428 (15)	−0.00138 (13)
O1	0.0264 (7)	0.0495 (9)	0.0963 (12)	0.0041 (5)	−0.0012 (7)	−0.0159 (8)
O2	0.1253 (16)	0.0347 (7)	0.0384 (7)	−0.0135 (9)	0.0154 (8)	0.0017 (6)
O3	0.0312 (6)	0.0428 (7)	0.0538 (8)	0.0005 (5)	0.0090 (5)	−0.0101 (6)
O4	0.0581 (8)	0.0317 (6)	0.0391 (6)	−0.0130 (5)	0.0045 (5)	0.0004 (5)
O5	0.0254 (6)	0.0346 (7)	0.0852 (11)	−0.0021 (5)	0.0041 (6)	−0.0049 (6)
N1	0.0289 (7)	0.0507 (9)	0.0457 (8)	−0.0105 (6)	0.0064 (6)	−0.0084 (7)
C1	0.0439 (9)	0.0337 (8)	0.0397 (9)	−0.0068 (7)	0.0086 (7)	−0.0045 (7)
C2	0.0329 (8)	0.0303 (8)	0.0424 (9)	0.0037 (6)	0.0052 (7)	−0.0022 (6)
C3	0.0268 (7)	0.0316 (8)	0.0376 (8)	−0.0003 (6)	0.0037 (6)	−0.0026 (6)
C4	0.0315 (8)	0.0308 (8)	0.0454 (9)	0.0034 (6)	0.0037 (7)	−0.0031 (7)
C5	0.0279 (8)	0.0485 (10)	0.0466 (9)	0.0043 (7)	0.0040 (7)	−0.0058 (8)

S1—O1	1.445 (1)	N1—H1	0.841 (10)
S1—O2	1.551 (2)	C1—C2	1.366 (2)
S1—O3	1.437 (1)	C1—H1A	0.945 (10)
S1—O4	1.454 (1)	C2—C3	1.400 (2)
S1—O2	1.5514 (15)	C2—H2A	0.938 (10)
O2—H2	0.848 (10)	C3—C4	1.397 (2)
O5—C3	1.3273 (19)	C4—C5	1.363 (2)
O5—H5	0.849 (10)	C4—H4	0.943 (9)
N1—C1	1.340 (2)	C5—H5A	0.947 (10)
N1—C5	1.341 (3)
O3—S1—O1	111.16 (8)	C2—C1—H1A	121.6 (13)
O3—S1—O4	114.04 (8)	C1—C2—C3	118.86 (16)
O1—S1—O4	112.73 (9)	C1—C2—H2A	119.0 (14)
O3—S1—O2	104.60 (9)	C3—C2—H2A	122.1 (14)
O1—S1—O2	106.91 (11)	O5—C3—C4	117.63 (15)
O4—S1—O2	106.71 (8)	O5—C3—C2	123.36 (15)
S1—O2—H2	113 (2)	C4—C3—C2	119.01 (15)
C3—O5—H5	107.5 (19)	C5—C4—C3	119.20 (16)
C1—N1—C5	121.59 (15)	C5—C4—H4	121.5 (12)
C1—N1—H1	119.2 (19)	C3—C4—H4	119.3 (12)
C5—N1—H1	119 (2)	N1—C5—C4	120.59 (16)
N1—C1—C2	120.75 (16)	N1—C5—H5A	116.9 (16)
N1—C1—H1A	117.6 (13)	C4—C5—H5A	122.5 (16)
C5—N1—C1—C2	−0.1 (3)	O5—C3—C4—C5	179.79 (17)
N1—C1—C2—C3	0.1 (3)	C2—C3—C4—C5	−0.4 (3)
C1—C2—C3—O5	179.94 (17)	C1—N1—C5—C4	−0.1 (3)
C1—C2—C3—C4	0.2 (2)	C3—C4—C5—N1	0.4 (3)

D—H···A	D—H	H···A	D···A	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)

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	D⋯A	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) ; (ii) .