3-Hydroxy-pyridinium hydrogen chloranilate monohydrate.

In the title salt hydrate, C(5)H(6)NO(+)·C(6)HCl(2)O(4) (-)·H(2)O, the three components are held together by O-H⋯O and N-H⋯O hydrogen bonds, as well as by C-H⋯O contacts, forming a double-tape structure along the c axis. Within each tape, the pyridinium ring and the chloranilate ring are almost coplanar, forming a dihedral angle of 2.35 (7)°.

Related literature

For related structures, see, for example: Gotoh et al. (2009a ▶,b ▶); Gotoh & Ishida (2009 ▶).

Experimental

Crystal data

C5H6NO+·C6HCl2O4 −·H2O

M = 322.10

Triclinic,

a = 7.4893 (13) Å

b = 9.6650 (17) Å

c = 9.9305 (17) Å

α = 88.129 (5)°

β = 68.404 (6)°

γ = 67.980 (4)°

V = 614.95 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.55 mm−1

T = 180 K

0.20 × 0.15 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID-II diffractometer

Absorption correction: numerical (; Higashi, 1999 ▶) T min = 0.907, T max = 0.973

12237 measured reflections

3572 independent reflections

2952 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.088

S = 1.07

3572 reflections

201 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.29 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046844/tk2567sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046844/tk2567Isup2.hkl

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

C5H6NO+·C6HCl2O4−·H2O	Z = 2
Mr = 322.10	F(000) = 328.00
Triclinic, P1	Dx = 1.739 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.4893 (13) Å	Cell parameters from 10001 reflections
b = 9.6650 (17) Å	θ = 3.0–30.1°
c = 9.9305 (17) Å	µ = 0.55 mm−1
α = 88.129 (5)°	T = 180 K
β = 68.404 (6)°	Block, brown
γ = 67.980 (4)°	0.20 × 0.15 × 0.05 mm
V = 614.95 (18) Å3

Rigaku R-AXIS RAPID-II diffractometer	2952 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.025
ω scans	θmax = 30.0°
Absorption correction: numerical (ABSCOR; Higashi, 1999)	h = −10→10
Tmin = 0.907, Tmax = 0.973	k = −13→13
12237 measured reflections	l = −13→13
3572 independent reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2238P] where P = (Fo2 + 2Fc2)/3
3572 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.74975 (5)	0.30013 (3)	0.52240 (3)	0.01897 (9)
Cl2	0.76493 (5)	0.94942 (3)	0.44706 (4)	0.02295 (10)
O1	0.77201 (16)	0.47186 (11)	0.26178 (10)	0.0198 (2)
O2	0.72724 (17)	0.51208 (11)	0.74674 (10)	0.0226 (2)
O3	0.73261 (17)	0.78687 (12)	0.71214 (11)	0.0244 (2)
O4	0.76878 (18)	0.74463 (12)	0.23264 (11)	0.0238 (2)
O5	0.7211 (2)	0.21895 (12)	0.23481 (11)	0.0277 (2)
O6	0.8140 (2)	0.62351 (14)	−0.02703 (12)	0.0284 (2)
N1	0.7338 (2)	0.25226 (14)	−0.13073 (13)	0.0229 (2)
C1	0.76153 (19)	0.53710 (14)	0.37347 (13)	0.0153 (2)
C2	0.7509 (2)	0.47845 (13)	0.50577 (13)	0.0152 (2)
C3	0.7388 (2)	0.55870 (14)	0.62593 (13)	0.0162 (2)
C4	0.7419 (2)	0.71690 (14)	0.60863 (14)	0.0173 (2)
C5	0.7570 (2)	0.77458 (14)	0.46900 (14)	0.0168 (2)
C6	0.7618 (2)	0.69224 (14)	0.35935 (14)	0.0165 (2)
C7	0.7293 (2)	0.29123 (15)	−0.00035 (15)	0.0199 (3)
H7	0.7272	0.3870	0.0215	0.024*
C8	0.7279 (2)	0.18979 (15)	0.10182 (14)	0.0190 (3)
C9	0.7317 (2)	0.05028 (15)	0.06603 (15)	0.0222 (3)
H9	0.7297	−0.0203	0.1348	0.027*
C10	0.7383 (2)	0.01496 (16)	−0.06979 (16)	0.0239 (3)
H10	0.7428	−0.0805	−0.0954	0.029*
C11	0.7382 (2)	0.11952 (17)	−0.16830 (15)	0.0252 (3)
H11	0.7413	0.0970	−0.2617	0.030*
H1	0.731 (3)	0.328 (2)	−0.188 (2)	0.041 (6)*
H6A	0.759 (4)	0.633 (3)	−0.084 (3)	0.067 (8)*
H6B	0.941 (5)	0.594 (3)	−0.081 (3)	0.061 (8)*
H4	0.762 (4)	0.690 (3)	0.182 (3)	0.063 (8)*
H5	0.739 (4)	0.301 (3)	0.235 (3)	0.060 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02939 (17)	0.01539 (14)	0.01838 (15)	−0.01195 (12)	−0.01284 (12)	0.00521 (11)
Cl2	0.03172 (18)	0.01444 (15)	0.02679 (18)	−0.01173 (13)	−0.01295 (14)	0.00362 (11)
O1	0.0324 (5)	0.0193 (4)	0.0138 (4)	−0.0142 (4)	−0.0113 (4)	0.0028 (3)
O2	0.0366 (6)	0.0214 (5)	0.0159 (4)	−0.0141 (4)	−0.0140 (4)	0.0051 (4)
O3	0.0360 (6)	0.0239 (5)	0.0181 (5)	−0.0149 (4)	−0.0120 (4)	−0.0016 (4)
O4	0.0443 (6)	0.0186 (5)	0.0171 (5)	−0.0168 (4)	−0.0166 (4)	0.0069 (4)
O5	0.0531 (7)	0.0237 (5)	0.0208 (5)	−0.0232 (5)	−0.0218 (5)	0.0071 (4)
O6	0.0357 (6)	0.0369 (6)	0.0159 (5)	−0.0149 (5)	−0.0124 (5)	0.0023 (4)
N1	0.0314 (6)	0.0236 (6)	0.0174 (5)	−0.0136 (5)	−0.0106 (5)	0.0073 (4)
C1	0.0189 (6)	0.0146 (5)	0.0145 (5)	−0.0077 (4)	−0.0076 (4)	0.0027 (4)
C2	0.0212 (6)	0.0130 (5)	0.0145 (6)	−0.0081 (4)	−0.0088 (5)	0.0029 (4)
C3	0.0192 (6)	0.0162 (5)	0.0152 (6)	−0.0077 (5)	−0.0079 (5)	0.0023 (4)
C4	0.0204 (6)	0.0180 (6)	0.0157 (6)	−0.0086 (5)	−0.0080 (5)	0.0011 (4)
C5	0.0218 (6)	0.0128 (5)	0.0185 (6)	−0.0086 (5)	−0.0088 (5)	0.0030 (4)
C6	0.0221 (6)	0.0152 (5)	0.0150 (6)	−0.0091 (5)	−0.0086 (5)	0.0043 (4)
C7	0.0272 (7)	0.0171 (6)	0.0191 (6)	−0.0114 (5)	−0.0101 (5)	0.0034 (5)
C8	0.0261 (7)	0.0181 (6)	0.0170 (6)	−0.0111 (5)	−0.0103 (5)	0.0026 (5)
C9	0.0340 (7)	0.0181 (6)	0.0202 (6)	−0.0134 (5)	−0.0134 (6)	0.0049 (5)
C10	0.0335 (7)	0.0206 (6)	0.0219 (7)	−0.0137 (6)	−0.0118 (6)	0.0002 (5)
C11	0.0344 (8)	0.0295 (7)	0.0162 (6)	−0.0157 (6)	−0.0113 (5)	0.0023 (5)

Cl1—C2	1.7289 (13)	C1—C2	1.4007 (17)
Cl2—C5	1.7172 (13)	C1—C6	1.5020 (17)
O1—C1	1.2564 (15)	C2—C3	1.4006 (17)
O2—C3	1.2519 (15)	C3—C4	1.5412 (18)
O3—C4	1.2149 (16)	C4—C5	1.4587 (18)
O4—C6	1.3313 (15)	C5—C6	1.3514 (18)
O4—H4	0.76 (3)	C7—C8	1.3877 (18)
O5—C8	1.3381 (16)	C7—H7	0.9500
O5—H5	0.85 (3)	C8—C9	1.3930 (18)
O6—H6A	0.80 (3)	C9—C10	1.3808 (19)
O6—H6B	0.84 (3)	C9—H9	0.9500
N1—C11	1.3330 (19)	C10—C11	1.383 (2)
N1—C7	1.3452 (18)	C10—H10	0.9500
N1—H1	0.91 (2)	C11—H11	0.9500
C6—O4—H4	111 (2)	C4—C5—Cl2	119.01 (9)
C8—O5—H5	106.0 (18)	O4—C6—C5	121.39 (11)
H6A—O6—H6B	103 (3)	O4—C6—C1	116.69 (11)
C11—N1—C7	123.32 (12)	C5—C6—C1	121.91 (11)
C11—N1—H1	125.1 (14)	N1—C7—C8	119.14 (12)
C7—N1—H1	111.6 (14)	N1—C7—H7	120.4
O1—C1—C2	126.22 (11)	C8—C7—H7	120.4
O1—C1—C6	115.16 (11)	O5—C8—C7	123.49 (12)
C2—C1—C6	118.62 (11)	O5—C8—C9	117.59 (12)
C3—C2—C1	122.83 (11)	C7—C8—C9	118.92 (12)
C3—C2—Cl1	118.48 (9)	C10—C9—C8	119.78 (13)
C1—C2—Cl1	118.68 (9)	C10—C9—H9	120.1
O2—C3—C2	125.37 (12)	C8—C9—H9	120.1
O2—C3—C4	116.88 (11)	C9—C10—C11	119.55 (13)
C2—C3—C4	117.75 (11)	C9—C10—H10	120.2
O3—C4—C5	123.42 (12)	C11—C10—H10	120.2
O3—C4—C3	118.12 (11)	N1—C11—C10	119.29 (13)
C5—C4—C3	118.46 (10)	N1—C11—H11	120.4
C6—C5—C4	120.38 (11)	C10—C11—H11	120.4
C6—C5—Cl2	120.61 (10)
O1—C1—C2—C3	−179.78 (13)	C4—C5—C6—O4	177.85 (12)
C6—C1—C2—C3	0.53 (19)	Cl2—C5—C6—O4	−1.29 (19)
O1—C1—C2—Cl1	−0.50 (19)	C4—C5—C6—C1	−2.7 (2)
C6—C1—C2—Cl1	179.80 (9)	Cl2—C5—C6—C1	178.13 (10)
C1—C2—C3—O2	179.38 (13)	O1—C1—C6—O4	1.29 (17)
Cl1—C2—C3—O2	0.10 (19)	C2—C1—C6—O4	−178.98 (12)
C1—C2—C3—C4	−1.25 (19)	O1—C1—C6—C5	−178.16 (12)
Cl1—C2—C3—C4	179.47 (9)	C2—C1—C6—C5	1.57 (19)
O2—C3—C4—O3	−0.19 (19)	C11—N1—C7—C8	−0.4 (2)
C2—C3—C4—O3	−179.62 (12)	N1—C7—C8—O5	−179.23 (13)
O2—C3—C4—C5	179.52 (12)	N1—C7—C8—C9	0.2 (2)
C2—C3—C4—C5	0.09 (18)	O5—C8—C9—C10	179.88 (14)
O3—C4—C5—C6	−178.41 (13)	C7—C8—C9—C10	0.5 (2)
C3—C4—C5—C6	1.89 (19)	C8—C9—C10—C11	−0.9 (2)
O3—C4—C5—Cl2	0.74 (19)	C7—N1—C11—C10	0.0 (2)
C3—C4—C5—Cl2	−178.96 (9)	C9—C10—C11—N1	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.911 (18)	1.867 (18)	2.7461 (17)	161.4 (18)
O4—H4···O1	0.77 (3)	2.21 (3)	2.6348 (16)	115 (2)
O4—H4···O6	0.77 (3)	2.04 (3)	2.7187 (17)	147 (3)
O5—H5···O1	0.85 (3)	1.80 (3)	2.6474 (17)	172 (3)
O6—H6A···O2i	0.80 (3)	2.21 (3)	2.8959 (18)	144 (3)
O6—H6A···O3i	0.80 (3)	2.50 (3)	3.1220 (17)	136 (3)
O6—H6B···O1ii	0.84 (4)	2.11 (3)	2.9281 (18)	164 (3)
C7—H7···O6	0.95	2.59	3.484 (2)	157
C9—H9···O4iii	0.95	2.40	3.3084 (18)	160
C10—H10···O3iv	0.95	2.38	3.163 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.911 (18)	1.867 (18)	2.7461 (17)	161.4 (18)
O4—H4⋯O1	0.77 (3)	2.21 (3)	2.6348 (16)	115 (2)
O4—H4⋯O6	0.77 (3)	2.04 (3)	2.7187 (17)	147 (3)
O5—H5⋯O1	0.85 (3)	1.80 (3)	2.6474 (17)	172 (3)
O6—H6A⋯O2i	0.80 (3)	2.21 (3)	2.8959 (18)	144 (3)
O6—H6A⋯O3i	0.80 (3)	2.50 (3)	3.1220 (17)	136 (3)
O6—H6B⋯O1ii	0.84 (4)	2.11 (3)	2.9281 (18)	164 (3)
C7—H7⋯O6	0.95	2.59	3.484 (2)	157
C9—H9⋯O4iii	0.95	2.40	3.3084 (18)	160
C10—H10⋯O3iv	0.95	2.38	3.163 (2)	140

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