2-Hy-droxy-pyridinium p-toluene-sulfonate.

In the title molecular salt, C(5)H(6)NO(+)·C(7)H(7)O(3)S(-), the cations and anions are connected by N-H⋯O and O-H⋯O hydrogen bonds, forming [100] chains.

Related literature

For general background on ferroelectric frameworks, see: Zhang et al. (2008 ▶, 2009 ▶, 2010 ▶). For related salts containing p-toluene­sulfonate anions, see: Helvenston et al. (2006 ▶); Collier et al. (2006 ▶); Koshima et al. (2001 ▶).

Experimental

Crystal data

C5H6NO+·C7H7O3S−

M = 267.29

Orthorhombic,

a = 10.293 (2) Å

b = 14.484 (3) Å

c = 15.708 (3) Å

V = 2341.8 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.3 × 0.3 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.489, T max = 1.000

23178 measured reflections

2688 independent reflections

2239 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.111

S = 1.09

2688 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019873/bh2431sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019873/bh2431Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019873/bh2431Isup3.cml

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

C5H6NO+·C7H7O3S−	F(000) = 1120
Mr = 267.29	Dx = 1.516 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3450 reflections
a = 10.293 (2) Å	θ = 6.2–55.3°
b = 14.484 (3) Å	µ = 0.28 mm−1
c = 15.708 (3) Å	T = 293 K
V = 2341.8 (8) Å3	Block, colourless
Z = 8	0.3 × 0.3 × 0.2 mm

Rigaku Mercury CCD diffractometer	2688 independent reflections
Radiation source: fine-focus sealed tube	2239 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −13→13
Tmin = 0.489, Tmax = 1.000	k = −18→18
23178 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0362P)2 + 1.2062P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2688 reflections	Δρmax = 0.26 e Å−3
169 parameters	Δρmin = −0.41 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0347 (16)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.5889 (2)	0.09901 (16)	0.81599 (13)	0.0461 (6)
H1A	0.6382	0.0453	0.8315	0.069*
H1B	0.4989	0.0890	0.8291	0.069*
H1C	0.6203	0.1514	0.8473	0.069*
C2	0.6034 (2)	0.11654 (13)	0.72297 (12)	0.0322 (4)
C3	0.5108 (2)	0.08731 (14)	0.66618 (13)	0.0356 (5)
H3	0.4365	0.0580	0.6862	0.043*
C4	0.52611 (19)	0.10060 (14)	0.58087 (12)	0.0335 (5)
H4	0.4625	0.0804	0.5431	0.040*
C5	0.63523 (18)	0.14370 (13)	0.55080 (12)	0.0277 (4)
C6	0.72725 (19)	0.17508 (14)	0.60638 (12)	0.0318 (4)
H6	0.8007	0.2055	0.5863	0.038*
C7	0.7102 (2)	0.16122 (13)	0.69220 (13)	0.0342 (5)
H7	0.7728	0.1827	0.7301	0.041*
C8	0.53344 (18)	0.14460 (13)	0.19333 (12)	0.0309 (4)
C9	0.65239 (19)	0.10354 (14)	0.20266 (13)	0.0352 (5)
H9	0.6890	0.0961	0.2564	0.042*
C10	0.7158 (2)	0.07393 (14)	0.13220 (14)	0.0401 (5)
H10	0.7970	0.0464	0.1378	0.048*
C11	0.6624 (2)	0.08387 (17)	0.05305 (14)	0.0446 (5)
H11	0.7052	0.0622	0.0049	0.054*
C12	0.5470 (2)	0.12556 (16)	0.04656 (14)	0.0424 (5)
H12	0.5097	0.1342	−0.0068	0.051*
N1	0.48537 (16)	0.15481 (12)	0.11587 (10)	0.0344 (4)
H1D	0.4112	0.1814	0.1101	0.041*
O1	0.45846 (14)	0.17554 (12)	0.25338 (10)	0.0446 (4)
H1	0.498 (3)	0.167 (2)	0.303 (2)	0.095 (12)*
O2	0.53381 (14)	0.17679 (12)	0.40618 (9)	0.0477 (4)
O3	0.70545 (15)	0.06576 (10)	0.41196 (9)	0.0426 (4)
O4	0.75191 (14)	0.22574 (10)	0.42828 (8)	0.0397 (4)
S1	0.65917 (5)	0.15323 (3)	0.44102 (3)	0.03132 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0660 (16)	0.0449 (13)	0.0273 (11)	−0.0031 (11)	0.0006 (10)	−0.0002 (9)
C2	0.0433 (11)	0.0285 (10)	0.0247 (9)	0.0050 (8)	−0.0003 (8)	−0.0014 (7)
C3	0.0343 (11)	0.0397 (11)	0.0326 (10)	−0.0038 (9)	0.0056 (9)	−0.0006 (9)
C4	0.0306 (10)	0.0415 (11)	0.0286 (10)	−0.0020 (8)	−0.0021 (8)	−0.0025 (9)
C5	0.0277 (9)	0.0317 (10)	0.0238 (9)	0.0053 (7)	0.0003 (7)	−0.0008 (7)
C6	0.0293 (10)	0.0340 (10)	0.0322 (10)	−0.0016 (8)	0.0004 (8)	0.0006 (8)
C7	0.0358 (11)	0.0358 (10)	0.0310 (10)	−0.0011 (8)	−0.0075 (8)	−0.0037 (8)
C8	0.0290 (10)	0.0348 (10)	0.0290 (10)	−0.0036 (8)	0.0013 (8)	0.0003 (8)
C9	0.0335 (11)	0.0398 (11)	0.0321 (10)	0.0004 (8)	−0.0045 (8)	0.0026 (9)
C10	0.0370 (11)	0.0381 (11)	0.0451 (12)	0.0086 (9)	0.0020 (9)	0.0002 (10)
C11	0.0507 (13)	0.0492 (13)	0.0338 (11)	0.0092 (11)	0.0069 (10)	−0.0043 (10)
C12	0.0469 (13)	0.0534 (13)	0.0269 (10)	0.0036 (10)	−0.0019 (9)	−0.0005 (10)
N1	0.0289 (8)	0.0432 (10)	0.0309 (9)	0.0013 (7)	−0.0033 (7)	0.0022 (7)
O1	0.0335 (8)	0.0702 (11)	0.0302 (8)	0.0100 (7)	0.0000 (6)	−0.0018 (8)
O2	0.0349 (8)	0.0804 (12)	0.0276 (7)	0.0126 (8)	−0.0024 (6)	0.0046 (8)
O3	0.0529 (9)	0.0417 (9)	0.0331 (8)	0.0064 (7)	0.0033 (7)	−0.0075 (6)
O4	0.0386 (8)	0.0428 (8)	0.0377 (8)	0.0030 (6)	0.0099 (6)	0.0051 (7)
S1	0.0296 (3)	0.0402 (3)	0.0241 (3)	0.0057 (2)	0.00163 (18)	0.0007 (2)

C1—C2	1.491 (3)	C8—N1	1.322 (2)
C1—H1A	0.9600	C8—C9	1.369 (3)
C1—H1B	0.9600	C9—C10	1.355 (3)
C1—H1C	0.9600	C9—H9	0.9300
C2—C7	1.364 (3)	C10—C11	1.367 (3)
C2—C3	1.373 (3)	C10—H10	0.9300
C3—C4	1.363 (3)	C11—C12	1.336 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.369 (3)	C12—N1	1.330 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.366 (3)	N1—H1D	0.8600
C5—S1	1.7474 (19)	O1—H1	0.89 (4)
C6—C7	1.374 (3)	O2—S1	1.4425 (15)
C6—H6	0.9300	O3—S1	1.4284 (15)
C7—H7	0.9300	O4—S1	1.4333 (16)
C8—O1	1.299 (2)
C2—C1—H1A	109.5	O1—C8—C9	127.14 (19)
C2—C1—H1B	109.5	N1—C8—C9	118.81 (18)
H1A—C1—H1B	109.5	C10—C9—C8	118.75 (19)
C2—C1—H1C	109.5	C10—C9—H9	120.6
H1A—C1—H1C	109.5	C8—C9—H9	120.6
H1B—C1—H1C	109.5	C9—C10—C11	121.1 (2)
C7—C2—C3	118.42 (18)	C9—C10—H10	119.5
C7—C2—C1	120.61 (19)	C11—C10—H10	119.5
C3—C2—C1	120.97 (19)	C12—C11—C10	118.3 (2)
C4—C3—C2	120.99 (19)	C12—C11—H11	120.8
C4—C3—H3	119.5	C10—C11—H11	120.8
C2—C3—H3	119.5	N1—C12—C11	120.4 (2)
C3—C4—C5	119.90 (18)	N1—C12—H12	119.8
C3—C4—H4	120.0	C11—C12—H12	119.8
C5—C4—H4	120.0	C8—N1—C12	122.64 (18)
C6—C5—C4	120.00 (18)	C8—N1—H1D	118.7
C6—C5—S1	120.44 (15)	C12—N1—H1D	118.7
C4—C5—S1	119.49 (15)	C8—O1—H1	109 (2)
C5—C6—C7	119.34 (19)	O3—S1—O4	112.53 (9)
C5—C6—H6	120.3	O3—S1—O2	112.76 (10)
C7—C6—H6	120.3	O4—S1—O2	111.68 (10)
C2—C7—C6	121.31 (18)	O3—S1—C5	107.00 (9)
C2—C7—H7	119.3	O4—S1—C5	106.83 (9)
C6—C7—H7	119.3	O2—S1—C5	105.48 (9)
O1—C8—N1	114.05 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.89 (4)	1.66 (4)	2.523 (2)	160 (3)
N1—H1D···O4i	0.86	1.86	2.704 (2)	166
O1—H1···S1	0.89 (4)	2.73 (4)	3.6139 (18)	169 (3)
N1—H1D···S1i	0.86	2.75	3.4747 (18)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.89 (4)	1.66 (4)	2.523 (2)	160 (3)
N1—H1D⋯O4i	0.86	1.86	2.704 (2)	166

Symmetry code: (i) .