organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages o835-o836

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

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 ππ stacking [centroid–centroid separation = 3.5175 (15) Å] occurs between the chains.

Related literature

For related structures, see: Seethalakshmi et al. (2006a[Seethalakshmi, T., Kaliannan, P., Venkatesan, P., Fronczek, F. R. & Thamotharan, S. (2006a). Acta Cryst. E62, o2353-o2355.],b[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006b). Acta Cryst. E62, o2560-o2562.],c[Seethalakshmi, T., Venkatesan, P., Fronczek, F. R., Kaliannan, P. & Thamotharan, S. (2006c). Acta Cryst. E62, o3389-o3390.], 2007[Seethalakshmi, T., Manivannan, S., Lynch, D. E., Dhanuskodi, S. & Kaliannan, P. (2007). Acta Cryst. E63, o599-o601.]). For related compounds, see: Dhanuskodi et al. (2006[Dhanuskodi, S., Manivannan, S. & Kirschbaum, K. (2006). Spectrochim. Acta Part A, 64, 504-511.], 2008[Dhanuskodi, S., Manivannan, S. & Philip, J. (2008). Spectrochim. Acta Part A, 69, 1207-1212.]).

[Scheme 1]

Experimental

Crystal data
  • C8H12NO+·Cl·H2O

  • Mr = 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[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.827, Tmax = 0.944

  • 9882 measured reflections

  • 2159 independent reflections

  • 1546 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.73 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

The positions of hydroxy H atom and H atoms of water molecule were determined from a difference Fourier map and refined freely along with their isotropic displacement parameters. In the final round of refinement, the O—H bond lengths of water molecule are restrained to 0.84 (2) Å. The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å), with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C and N—C bonds. The remaining H atoms were placed in geometrically idealized positions (C—H = 0.95 Å), with Uiso(H) = 1.2Ueq(C) and were constrained to ride on their parent atoms.

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
[Figure 1] Fig. 1. Molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] 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.
[Figure 3] 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.
[Figure 4] Fig. 4. Part of the crystal structure showing a helical chain formed by C—H···Cl intermolecular interactions.
[Figure 5] 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·H2OF(000) = 408
Mr = 191.65Dx = 1.347 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1861 reflections
a = 8.2548 (11) Åθ = 1.0–27.5°
b = 8.4781 (9) ŵ = 0.37 mm1
c = 13.6714 (18) ÅT = 120 K
β = 99.064 (6)°Prism, colourless
V = 944.8 (2) Å30.54 × 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 anode1546 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1011
Tmin = 0.827, Tmax = 0.944l = 1717
9882 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H 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 parametersΔρmax = 0.73 e Å3
2 restraintsΔρmin = 0.48 e Å3
Crystal data top
C8H12NO+·Cl·H2OV = 944.8 (2) Å3
Mr = 191.65Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.2548 (11) ŵ = 0.37 mm1
b = 8.4781 (9) ÅT = 120 K
c = 13.6714 (18) Å0.54 × 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)
Tmin = 0.827, Tmax = 0.944Rint = 0.069
9882 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0612 restraints
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.73 e Å3
2159 reflectionsΔρmin = 0.48 e Å3
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
xyzUiso*/Ueq
Cl10.45702 (8)0.08706 (8)0.25244 (5)0.0322 (3)
O10.8028 (3)0.2941 (2)0.48865 (16)0.0335 (5)
O1W0.3198 (3)0.3719 (2)0.35499 (17)0.0347 (5)
N10.7943 (3)0.1762 (3)0.42120 (16)0.0267 (5)
C20.7200 (3)0.1258 (3)0.49853 (19)0.0261 (6)
C30.7204 (3)0.0310 (3)0.5220 (2)0.0275 (6)
H30.66860.06570.57550.033*
C40.7963 (3)0.1405 (3)0.4678 (2)0.0269 (6)
C50.8682 (3)0.0865 (3)0.3885 (2)0.0277 (6)
H50.91950.15920.35020.033*
C60.8655 (3)0.0716 (3)0.3651 (2)0.0272 (6)
C70.9402 (4)0.1291 (4)0.2790 (2)0.0350 (7)
H7A0.85490.17680.22990.053*
H7B0.98990.04010.24880.053*
H7C1.02460.20790.30170.053*
C80.7926 (4)0.3475 (3)0.3986 (2)0.0359 (7)
H8A0.84910.36610.34170.054*
H8B0.84860.40520.45620.054*
H8C0.67890.38410.38280.054*
C90.6423 (4)0.2444 (3)0.5574 (2)0.0333 (7)
H9A0.72670.31530.59130.050*
H9B0.58780.19000.60640.050*
H9C0.56120.30590.51290.050*
H10.758 (4)0.306 (4)0.538 (3)0.040 (10)*
H1W0.344 (5)0.306 (4)0.316 (2)0.059 (12)*
H2W0.250 (4)0.423 (4)0.319 (3)0.076 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0365 (4)0.0264 (4)0.0339 (4)0.0008 (3)0.0058 (3)0.0006 (3)
O10.0452 (12)0.0180 (9)0.0385 (12)0.0037 (8)0.0100 (10)0.0015 (8)
O1W0.0431 (12)0.0233 (10)0.0373 (12)0.0021 (9)0.0053 (10)0.0010 (9)
N10.0299 (12)0.0175 (11)0.0321 (13)0.0008 (9)0.0028 (9)0.0003 (9)
C20.0268 (13)0.0220 (12)0.0278 (14)0.0005 (10)0.0008 (11)0.0022 (10)
C30.0294 (13)0.0247 (13)0.0278 (14)0.0006 (11)0.0023 (11)0.0003 (11)
C40.0301 (14)0.0192 (12)0.0299 (14)0.0001 (11)0.0002 (11)0.0025 (11)
C50.0302 (14)0.0235 (14)0.0288 (14)0.0011 (11)0.0031 (11)0.0017 (10)
C60.0266 (13)0.0255 (14)0.0287 (14)0.0020 (10)0.0015 (11)0.0024 (11)
C70.0392 (16)0.0300 (14)0.0364 (16)0.0040 (12)0.0076 (12)0.0002 (13)
C80.0434 (17)0.0168 (13)0.0483 (18)0.0002 (12)0.0098 (14)0.0034 (12)
C90.0399 (16)0.0242 (14)0.0351 (16)0.0015 (12)0.0041 (12)0.0051 (12)
Geometric parameters (Å, º) top
O1—C41.333 (3)C5—C61.378 (4)
O1—H10.82 (4)C5—H50.9500
O1W—H1W0.812 (19)C6—C71.494 (4)
O1W—H2W0.824 (19)C7—H7A0.9800
N1—C61.364 (3)C7—H7B0.9800
N1—C21.372 (3)C7—H7C0.9800
N1—C81.484 (3)C8—H8A0.9800
C2—C31.367 (4)C8—H8B0.9800
C2—C91.495 (4)C8—H8C0.9800
C3—C41.396 (4)C9—H9A0.9800
C3—H30.9500C9—H9B0.9800
C4—C51.394 (4)C9—H9C0.9800
C4—O1—H1107 (2)C5—C6—C7120.4 (3)
H1W—O1W—H2W101 (4)C6—C7—H7A109.5
C6—N1—C2121.0 (2)C6—C7—H7B109.5
C6—N1—C8120.6 (2)H7A—C7—H7B109.5
C2—N1—C8118.4 (2)C6—C7—H7C109.5
C3—C2—N1120.0 (2)H7A—C7—H7C109.5
C3—C2—C9120.9 (2)H7B—C7—H7C109.5
N1—C2—C9119.1 (2)N1—C8—H8A109.5
C2—C3—C4120.4 (3)N1—C8—H8B109.5
C2—C3—H3119.8H8A—C8—H8B109.5
C4—C3—H3119.8N1—C8—H8C109.5
O1—C4—C5118.6 (2)H8A—C8—H8C109.5
O1—C4—C3122.9 (3)H8B—C8—H8C109.5
C5—C4—C3118.5 (2)C2—C9—H9A109.5
C6—C5—C4120.5 (3)C2—C9—H9B109.5
C6—C5—H5119.8H9A—C9—H9B109.5
C4—C5—H5119.8C2—C9—H9C109.5
N1—C6—C5119.7 (3)H9A—C9—H9C109.5
N1—C6—C7119.9 (2)H9B—C9—H9C109.5
C6—N1—C2—C31.8 (4)O1—C4—C5—C6179.4 (3)
C8—N1—C2—C3179.5 (3)C3—C4—C5—C60.7 (4)
C6—N1—C2—C9179.4 (2)C2—N1—C6—C52.4 (4)
C8—N1—C2—C90.7 (3)C8—N1—C6—C5178.9 (3)
N1—C2—C3—C40.1 (4)C2—N1—C6—C7177.7 (2)
C9—C2—C3—C4178.7 (2)C8—N1—C6—C71.0 (4)
C2—C3—C4—O1178.7 (3)C4—C5—C6—N11.2 (4)
C2—C3—C4—C51.3 (4)C4—C5—C6—C7179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.82 (4)1.78 (4)2.591 (3)168 (4)
O1W—H1W···Cl10.81 (2)2.31 (2)3.095 (2)162 (4)
O1W—H2W···Cl1ii0.82 (2)2.30 (2)3.106 (2)168 (4)
C3—H3···Cl1i0.952.723.647 (3)165
C9—H9A···Cl1iii0.982.803.704 (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 formulaC8H12NO+·Cl·H2O
Mr191.65
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)8.2548 (11), 8.4781 (9), 13.6714 (18)
β (°) 99.064 (6)
V3)944.8 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.54 × 0.42 × 0.16
Data collection
DiffractometerBruker–Nonius 95mm CCD camera on κ-goniostat
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.827, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections
9882, 2159, 1546
Rint0.069
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.174, 1.02
No. of reflections2159
No. of parameters124
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.82 (4)1.78 (4)2.591 (3)168 (4)
O1W—H1W···Cl10.812 (19)2.31 (2)3.095 (2)162 (4)
O1W—H2W···Cl1ii0.824 (19)2.30 (2)3.106 (2)168 (4)
C3—H3···Cl1i0.952.723.647 (3)165
C9—H9A···Cl1iii0.982.803.704 (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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Volume 69| Part 6| June 2013| Pages o835-o836
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