4-Hy­droxy-1,2,6-tri­methyl­pyridinium chloride monohydrate

Seethalakshmi, T.; Manivannan, S.; Dhanuskodi, S.; Lynch, D.E.; Thamotharan, S.

doi:10.1107/S1600536813011616

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o835-o836

doi:10.1107/S1600536813011616

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4-Hydroxy-1,2,6-trimethylpyridinium chloride monohydrate

T. Seethalakshmi,^a ^* S. Manivannan,^b S. Dhanuskodi,^c Daniel E. Lynch ^d and S. Thamotharan ^e

^aDepartment of Physics, Government Arts College (Autonomous), Karur 639 005, India, ^bCarbon Nanomaterials Laboratory, Department of Physics, National Institute of Technology, Tiruchirappalli 620 015, India, ^cSchool of Physics, Bharathidasan University, Tiruchirappalli 620 024, India, ^dFaculty of Health and Life Sciences, Coventry University, Coventry CV1 5FB, England, and ^eDepartment of Bioinformatics, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613 401, India
^*Correspondence e-mail: seetha_b2002@yahoo.com

(Received 23 April 2013; accepted 28 April 2013; online 4 May 2013)

In the crystal of the title hydrated molecular salt, C₈H₁₂NO⁺·Cl⁻·H₂O, the water molecule makes two O—H⋯Cl hydrogen bonds, generating [010] zigzag chains of alternating water molecules and chloride ions. The cation is bonded to the chain by an O—H⋯O hydrogen bond and two weak C—H⋯Cl interactions. 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_r = 191.65
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.174
S = 1.02
2159 reflections
124 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813011616/hb7075sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813011616/hb7075Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies on 4-hydroxypyridinum salts (Seethalakshmi et al., 2007, Dhanuskodi et al., 2006, 2008), we report here the crystal structure of N-methyl-2,6-dimethyl-4-hydroxypyridinium chloride monohydrate (I), (Fig. 1).

The corresponding bond lengths and angles of the cation in (I) are comparable with those of related structures reported earlier (Seethalakshmi et al., 2006a,b,c, 2007).

In (I), water molecule acts as a donor for two different symmetry-related chloride anions and acts as an acceptor for the hydroxy group of the cation. As shown in Fig.2, the water molecule and chloride anion are interlinked by O—H···Cl intermolecular hydrogen bond. This interaction links the water molecule and the chloride anion alternately into a one-dimensional chain which runs paralell to the b axis. The cation molecules in the crystal structure are interlinked via two types of cooperative hydrogen bonding modes (Fig. 3). For example, the glide related cation molecules are interconnected by O—H···O—H···Cl···H—O···H—O cooperative hydrogen bonding pattern, whereas cations are related by translation interlinked via another type of O—H···O—H···Cl···H—O—H···Cl···H—O···H—O cooperative hydrogen bonding pattern.

The title salt (I), also features a network of weak intermolecular C—H···Cl interactions. Atoms C3 (via H3) and C9 (via H9A) of cation are involved in weak C—H···Cl intermolecular interactions with two different chloride anions. These weak intermolecular interactions link the cations through chloride anions and generates a helical chain which runs paralell to b axis. The chloride anions are located approximately at the middle of the helical axis (Fig. 4).

As shown in Fig. 5, an R²₃(8) loop is formed by the combination of O—H···O1W and O1W—H1W···Cl and C3—H3···Cl intermolecular interactions. As mentioned earlier, one of the methyl atoms C9 (via H9A) is participated in a weak intermolecular C—H···Cl interaction with chloride anion. Again, this interaction combines with C3—H3···Cl and two O1w—H···Cl interactions forming a ring which has a graph-set motif of R²₄(10). The R²₃(8) and R²₄(10) ring motifs are arranged alternately as a helical ribbon which run parallel to the b axis (Fig. 5). In the solid state, each chloride anion is tetra coordinated by two cations (via H3 and H9A) and two water molecules (via H1W and H2W). The tetra coordination angles in the range of 58.40–88.17°. There is a π···π stacking interaction also observed between two pyridinium rings related by center of inversion with centroid-to-centroid distance of 3.5175 (15) Å.

Related literature top

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

Experimental top

The title salt was prepared by dissolving 1-methyl-2,6-dimethyl-4-hydroxypyridine (1.37 g) with HCl (0.92 ml) in distilled water (5 ml). The mixture was stirred at room temperature for 7 h and the clear solution was kept for evaporation at 60 °C after filtration. Finally crystalline powder was obtained and dissolved in distilled water. Colourless prisms were obtained following the slow evoporation technique.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. One dimensional chain generated from alternate water and chloride anion interconnected by O—H···Cl hydrogen bond which runs parallel to the b axis.
	Fig. 3. Part of the crystal structure showing O—H···O—H···Cl···H—O···H—O and O—H···O—H···Cl···H—O—H···Cl···H—O···H—O cooperative hydrogen bonding modes interconnects two cations related by translation and glide, respectively. For clarity, H atoms not involved in the hydrogen bonds have been omitted.
	Fig. 4. Part of the crystal structure showing a helical chain formed by C—H···Cl intermolecular interactions.
	Fig. 5. Arrangement of alternate R²₃(8) and R²₄(10) ring motifs.

4-Hydroxy-1,2,6-trimethylpyridinium chloride monohydrate top

Crystal data top

C₈H₁₂NO⁺·Cl⁻·H₂O	F(000) = 408
M_r = 191.65	D_x = 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

Data collection top

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	R_int = 0.069
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→11
T_min = 0.827, T_max = 0.944	l = −17→17
9882 measured reflections

Refinement top

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(F_o²) + (0.1015P)² + 0.5878P] where P = (F_o² + 2F_c²)/3
2159 reflections	(Δ/σ)_max < 0.001
124 parameters	Δρ_max = 0.73 e Å⁻³
2 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₈H₁₂NO⁺·Cl⁻·H₂O	V = 944.8 (2) Å³
M_r = 191.65	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2548 (11) Å	µ = 0.37 mm⁻¹
b = 8.4781 (9) Å	T = 120 K
c = 13.6714 (18) Å	0.54 × 0.42 × 0.16 mm
β = 99.064 (6)°

Data collection top

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	2159 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1546 reflections with I > 2σ(I)
T_min = 0.827, T_max = 0.944	R_int = 0.069
9882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	2 restraints
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.73 e Å⁻³
2159 reflections	Δρ_min = −0.48 e Å⁻³
124 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₁₂NO⁺·Cl⁻·H₂O
M_r	191.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	8.2548 (11), 8.4781 (9), 13.6714 (18)
β (°)	99.064 (6)
V (Å³)	944.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.54 × 0.42 × 0.16

Data collection
Diffractometer	Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.827, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	9882, 2159, 1546
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.174, 1.02
No. of reflections	2159
No. of parameters	124
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.48

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.812 (19)	2.31 (2)	3.095 (2)	162 (4)
O1W—H2W···Cl1ⁱⁱ	0.824 (19)	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) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors thank the EPSRC National Crystallography Service (University of Southampton, UK) for the X-ray data collection. ST thanks the management of SASTRA University for their encouragement.

References

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