4-Hy-droxy-1,2,6-tri-methyl-pyridinium chloride monohydrate.

In the crystal of the title hydrated mol-ecular salt, C8H12NO(+)·Cl(-)·H2O, the water mol-ecule makes two O-H⋯Cl hydrogen bonds, generating [010] zigzag chains of alternating water mol-ecules and chloride ions. The cation is bonded to the chain by an O-H⋯O hydrogen bond and two weak C-H⋯Cl inter-actions. Weak aromatic π-π stacking [centroid-centroid separation = 3.5175 (15) Å] occurs between the chains.

Related literature

For related structures, see: Seethalakshmi et al. (2006a ▶,b ▶,c ▶, 2007 ▶). For related compounds, see: Dhanuskodi et al. (2006 ▶, 2008 ▶).

Experimental

Crystal data

C8H12NO+·Cl−·H2O

M = 191.65

Monoclinic,

a = 8.2548 (11) Å

b = 8.4781 (9) Å

c = 13.6714 (18) Å

β = 99.064 (6)°

V = 944.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 120 K

0.54 × 0.42 × 0.16 mm

Data collection

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.827, T max = 0.944

9882 measured reflections

2159 independent reflections

1546 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.174

S = 1.02

2159 reflections

124 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.48 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011616/hb7075sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011616/hb7075Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011616/hb7075Isup3.cml

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

C8H12NO+·Cl−·H2O	F(000) = 408
Mr = 191.65	Dx = 1.347 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1861 reflections
a = 8.2548 (11) Å	θ = 1.0–27.5°
b = 8.4781 (9) Å	µ = 0.37 mm−1
c = 13.6714 (18) Å	T = 120 K
β = 99.064 (6)°	Prism, colourless
V = 944.8 (2) Å3	0.54 × 0.42 × 0.16 mm
Z = 4

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	2159 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1546 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→11
Tmin = 0.827, Tmax = 0.944	l = −17→17
9882 measured 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1015P)2 + 0.5878P] where P = (Fo2 + 2Fc2)/3
2159 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.73 e Å−3
2 restraints	Δρmin = −0.48 e Å−3

Experimental. The minimum and maximum absorption values stated above are those calculated in SHELXL97 from the given crystal dimensions. The ratio of minimum to maximum apparent transmission was determined experimentally as 0.597412.

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	0.45702 (8)	0.08706 (8)	0.25244 (5)	0.0322 (3)
O1	0.8028 (3)	−0.2941 (2)	0.48865 (16)	0.0335 (5)
O1W	0.3198 (3)	0.3719 (2)	0.35499 (17)	0.0347 (5)
N1	0.7943 (3)	0.1762 (3)	0.42120 (16)	0.0267 (5)
C2	0.7200 (3)	0.1258 (3)	0.49853 (19)	0.0261 (6)
C3	0.7204 (3)	−0.0310 (3)	0.5220 (2)	0.0275 (6)
H3	0.6686	−0.0657	0.5755	0.033*
C4	0.7963 (3)	−0.1405 (3)	0.4678 (2)	0.0269 (6)
C5	0.8682 (3)	−0.0865 (3)	0.3885 (2)	0.0277 (6)
H5	0.9195	−0.1592	0.3502	0.033*
C6	0.8655 (3)	0.0716 (3)	0.3651 (2)	0.0272 (6)
C7	0.9402 (4)	0.1291 (4)	0.2790 (2)	0.0350 (7)
H7A	0.8549	0.1768	0.2299	0.053*
H7B	0.9899	0.0401	0.2488	0.053*
H7C	1.0246	0.2079	0.3017	0.053*
C8	0.7926 (4)	0.3475 (3)	0.3986 (2)	0.0359 (7)
H8A	0.8491	0.3661	0.3417	0.054*
H8B	0.8486	0.4052	0.4562	0.054*
H8C	0.6789	0.3841	0.3828	0.054*
C9	0.6423 (4)	0.2444 (3)	0.5574 (2)	0.0333 (7)
H9A	0.7267	0.3153	0.5913	0.050*
H9B	0.5878	0.1900	0.6064	0.050*
H9C	0.5612	0.3059	0.5129	0.050*
H1	0.758 (4)	−0.306 (4)	0.538 (3)	0.040 (10)*
H1W	0.344 (5)	0.306 (4)	0.316 (2)	0.059 (12)*
H2W	0.250 (4)	0.423 (4)	0.319 (3)	0.076 (15)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0365 (4)	0.0264 (4)	0.0339 (4)	0.0008 (3)	0.0058 (3)	−0.0006 (3)
O1	0.0452 (12)	0.0180 (9)	0.0385 (12)	0.0037 (8)	0.0100 (10)	0.0015 (8)
O1W	0.0431 (12)	0.0233 (10)	0.0373 (12)	0.0021 (9)	0.0053 (10)	0.0010 (9)
N1	0.0299 (12)	0.0175 (11)	0.0321 (13)	−0.0008 (9)	0.0028 (9)	−0.0003 (9)
C2	0.0268 (13)	0.0220 (12)	0.0278 (14)	0.0005 (10)	−0.0008 (11)	−0.0022 (10)
C3	0.0294 (13)	0.0247 (13)	0.0278 (14)	−0.0006 (11)	0.0023 (11)	−0.0003 (11)
C4	0.0301 (14)	0.0192 (12)	0.0299 (14)	−0.0001 (11)	−0.0002 (11)	−0.0025 (11)
C5	0.0302 (14)	0.0235 (14)	0.0288 (14)	0.0011 (11)	0.0031 (11)	−0.0017 (10)
C6	0.0266 (13)	0.0255 (14)	0.0287 (14)	−0.0020 (10)	0.0015 (11)	−0.0024 (11)
C7	0.0392 (16)	0.0300 (14)	0.0364 (16)	−0.0040 (12)	0.0076 (12)	0.0002 (13)
C8	0.0434 (17)	0.0168 (13)	0.0483 (18)	0.0002 (12)	0.0098 (14)	0.0034 (12)
C9	0.0399 (16)	0.0242 (14)	0.0351 (16)	0.0015 (12)	0.0041 (12)	−0.0051 (12)

O1—C4	1.333 (3)	C5—C6	1.378 (4)
O1—H1	0.82 (4)	C5—H5	0.9500
O1W—H1W	0.812 (19)	C6—C7	1.494 (4)
O1W—H2W	0.824 (19)	C7—H7A	0.9800
N1—C6	1.364 (3)	C7—H7B	0.9800
N1—C2	1.372 (3)	C7—H7C	0.9800
N1—C8	1.484 (3)	C8—H8A	0.9800
C2—C3	1.367 (4)	C8—H8B	0.9800
C2—C9	1.495 (4)	C8—H8C	0.9800
C3—C4	1.396 (4)	C9—H9A	0.9800
C3—H3	0.9500	C9—H9B	0.9800
C4—C5	1.394 (4)	C9—H9C	0.9800
C4—O1—H1	107 (2)	C5—C6—C7	120.4 (3)
H1W—O1W—H2W	101 (4)	C6—C7—H7A	109.5
C6—N1—C2	121.0 (2)	C6—C7—H7B	109.5
C6—N1—C8	120.6 (2)	H7A—C7—H7B	109.5
C2—N1—C8	118.4 (2)	C6—C7—H7C	109.5
C3—C2—N1	120.0 (2)	H7A—C7—H7C	109.5
C3—C2—C9	120.9 (2)	H7B—C7—H7C	109.5
N1—C2—C9	119.1 (2)	N1—C8—H8A	109.5
C2—C3—C4	120.4 (3)	N1—C8—H8B	109.5
C2—C3—H3	119.8	H8A—C8—H8B	109.5
C4—C3—H3	119.8	N1—C8—H8C	109.5
O1—C4—C5	118.6 (2)	H8A—C8—H8C	109.5
O1—C4—C3	122.9 (3)	H8B—C8—H8C	109.5
C5—C4—C3	118.5 (2)	C2—C9—H9A	109.5
C6—C5—C4	120.5 (3)	C2—C9—H9B	109.5
C6—C5—H5	119.8	H9A—C9—H9B	109.5
C4—C5—H5	119.8	C2—C9—H9C	109.5
N1—C6—C5	119.7 (3)	H9A—C9—H9C	109.5
N1—C6—C7	119.9 (2)	H9B—C9—H9C	109.5
C6—N1—C2—C3	1.8 (4)	O1—C4—C5—C6	−179.4 (3)
C8—N1—C2—C3	−179.5 (3)	C3—C4—C5—C6	0.7 (4)
C6—N1—C2—C9	−179.4 (2)	C2—N1—C6—C5	−2.4 (4)
C8—N1—C2—C9	−0.7 (3)	C8—N1—C6—C5	178.9 (3)
N1—C2—C3—C4	0.1 (4)	C2—N1—C6—C7	177.7 (2)
C9—C2—C3—C4	−178.7 (2)	C8—N1—C6—C7	−1.0 (4)
C2—C3—C4—O1	178.7 (3)	C4—C5—C6—N1	1.2 (4)
C2—C3—C4—C5	−1.3 (4)	C4—C5—C6—C7	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Wi	0.82 (4)	1.78 (4)	2.591 (3)	168 (4)
O1W—H1W···Cl1	0.81 (2)	2.31 (2)	3.095 (2)	162 (4)
O1W—H2W···Cl1ii	0.82 (2)	2.30 (2)	3.106 (2)	168 (4)
C3—H3···Cl1i	0.95	2.72	3.647 (3)	165
C9—H9A···Cl1iii	0.98	2.80	3.704 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1W i	0.82 (4)	1.78 (4)	2.591 (3)	168 (4)
O1W—H1W⋯Cl1	0.81 (2)	2.31 (2)	3.095 (2)	162 (4)
O1W—H2W⋯Cl1ii	0.82 (2)	2.30 (2)	3.106 (2)	168 (4)
C3—H3⋯Cl1i	0.95	2.72	3.647 (3)	165
C9—H9A⋯Cl1iii	0.98	2.80	3.704 (3)	154

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