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

The title salt, C8H12NO(+)·Br(-)·H2O, is isomorphous with the chloride analogue [Seethalakshmi et al. (2013). Acta Cryst. E69, o835-o836]. In the solid state, the cations, anions and water mol-ecules are inter-linked by a network of O-H⋯O, O-H⋯Br and C-H⋯Br inter-actions. The water mol-ecule makes two O-H⋯Br hydrogen bonds, generating [010] zigzag chains of alternating water mol-ecules and bromide anions. The cation is involved in two inter-molecular C-H⋯Cl inter-actions in the chloride salt, whereas three inter-molecular C-H⋯Br inter-actions are observed in the title bromide salt. This additional inter-molecular C-H⋯Br inter-action links the adjacent water and bromide zigzag chains via cationic mol-ecules. In addition, weak π-π stacking inter-actions are observed between pyridinium rings [centroid-centroid distance = 3.5664 (13) Å].

Related literature

For related structures, see: Seethalakshmi et al. (2006a ▶,b ▶,c ▶, 2007 ▶, 2013a ▶,b ▶). For related compounds, see: Dhanuskodi et al. (2006 ▶, 2008 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H12NO+·Br−·H2O

M = 236.11

Monoclinic,

a = 8.4796 (4) Å

b = 8.5874 (6) Å

c = 13.8479 (9) Å

β = 99.504 (4)°

V = 994.53 (11) Å3

Z = 4

Mo Kα radiation

μ = 4.10 mm−1

T = 120 K

0.30 × 0.30 × 0.25 mm

Data collection

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

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.373, T max = 0.427

11830 measured reflections

2277 independent reflections

1888 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.056

S = 1.06

2277 reflections

125 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; method used to solve structure: isomorphous; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: 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/S1600536813013330/tk5224sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013330/tk5224Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013330/tk5224Isup3.cml

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

C8H12NO+·Br−·H2O	F(000) = 480
Mr = 236.11	Dx = 1.577 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2311 reflections
a = 8.4796 (4) Å	θ = 1–27.5°
b = 8.5874 (6) Å	µ = 4.10 mm−1
c = 13.8479 (9) Å	T = 120 K
β = 99.504 (4)°	Block, colourless
V = 994.53 (11) Å3	0.30 × 0.30 × 0.25 mm
Z = 4

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	2277 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→11
Tmin = 0.373, Tmax = 0.427	l = −17→17
11830 measured reflections

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056	w = 1/[σ2(Fo2) + (0.0179P)2 + 0.9223P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2277 reflections	Δρmax = 0.59 e Å−3
125 parameters	Δρmin = −0.34 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (5)

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 0.696421.

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
Br1	0.46272 (3)	0.08691 (3)	0.252474 (16)	0.02160 (9)
O1	0.8002 (2)	−0.29194 (18)	0.48421 (13)	0.0265 (4)
O1W	0.3258 (2)	0.3759 (2)	0.36438 (13)	0.0270 (4)
N1	0.7983 (2)	0.1745 (2)	0.42283 (14)	0.0185 (4)
C2	0.7227 (2)	0.1241 (2)	0.49673 (16)	0.0175 (4)
C3	0.7211 (3)	−0.0319 (3)	0.51871 (16)	0.0185 (5)
H3	0.6689	−0.0670	0.5703	0.022*
C4	0.7960 (3)	−0.1390 (3)	0.46562 (17)	0.0196 (5)
C5	0.8699 (3)	−0.0850 (3)	0.38918 (16)	0.0199 (5)
H5	0.9208	−0.1565	0.3519	0.024*
C6	0.8691 (2)	0.0712 (3)	0.36768 (16)	0.0190 (5)
C7	0.9436 (3)	0.1302 (3)	0.28400 (18)	0.0278 (5)
H7A	0.8608	0.1764	0.2346	0.042*
H7B	0.9945	0.0436	0.2548	0.042*
H7C	1.0241	0.2091	0.3078	0.042*
C8	0.7984 (3)	0.3436 (3)	0.4015 (2)	0.0284 (6)
H8A	0.6880	0.3802	0.3832	0.043*
H8B	0.8572	0.3627	0.3474	0.043*
H8C	0.8501	0.3999	0.4598	0.043*
C9	0.6442 (3)	0.2398 (3)	0.55408 (17)	0.0236 (5)
H9A	0.7252	0.3102	0.5889	0.035*
H9B	0.5904	0.1849	0.6015	0.035*
H9C	0.5654	0.3002	0.5094	0.035*
H1	0.756 (3)	−0.313 (3)	0.5317 (17)	0.038 (9)*
H1W	0.355 (3)	0.309 (3)	0.330 (2)	0.044 (9)*
H2W	0.261 (4)	0.432 (3)	0.328 (2)	0.062 (11)*

	U11	U22	U33	U12	U13	U23
Br1	0.02104 (13)	0.01973 (12)	0.02404 (14)	−0.00007 (9)	0.00380 (8)	0.00019 (10)
O1	0.0352 (10)	0.0132 (8)	0.0329 (10)	0.0028 (7)	0.0108 (8)	0.0001 (7)
O1W	0.0316 (10)	0.0181 (9)	0.0307 (10)	0.0045 (7)	0.0037 (8)	0.0019 (8)
N1	0.0166 (9)	0.0138 (9)	0.0242 (11)	−0.0018 (7)	0.0010 (7)	−0.0019 (7)
C2	0.0132 (10)	0.0179 (11)	0.0201 (12)	−0.0013 (8)	−0.0015 (8)	−0.0028 (9)
C3	0.0174 (11)	0.0195 (11)	0.0181 (12)	−0.0001 (8)	0.0014 (9)	−0.0010 (9)
C4	0.0177 (11)	0.0157 (10)	0.0240 (12)	0.0007 (8)	−0.0007 (9)	−0.0013 (9)
C5	0.0177 (11)	0.0185 (10)	0.0229 (12)	0.0004 (9)	0.0013 (9)	−0.0044 (9)
C6	0.0143 (10)	0.0216 (11)	0.0203 (11)	−0.0026 (9)	0.0002 (8)	−0.0021 (9)
C7	0.0273 (13)	0.0305 (13)	0.0268 (13)	−0.0025 (10)	0.0079 (10)	0.0022 (10)
C8	0.0300 (13)	0.0153 (11)	0.0407 (16)	0.0003 (10)	0.0081 (11)	0.0041 (10)
C9	0.0254 (12)	0.0179 (11)	0.0268 (13)	0.0035 (9)	0.0024 (9)	−0.0033 (10)

O1—C4	1.338 (3)	C5—C6	1.374 (3)
O1—H1	0.828 (17)	C5—H5	0.9500
O1W—H1W	0.813 (17)	C6—C7	1.496 (3)
O1W—H2W	0.833 (18)	C7—H7A	0.9800
N1—C2	1.365 (3)	C7—H7B	0.9800
N1—C6	1.372 (3)	C7—H7C	0.9800
N1—C8	1.482 (3)	C8—H8A	0.9800
C2—C3	1.374 (3)	C8—H8B	0.9800
C2—C9	1.496 (3)	C8—H8C	0.9800
C3—C4	1.394 (3)	C9—H9A	0.9800
C3—H3	0.9500	C9—H9B	0.9800
C4—C5	1.395 (3)	C9—H9C	0.9800
C4—O1—H1	111 (2)	C5—C6—C7	120.7 (2)
H1W—O1W—H2W	107 (3)	C6—C7—H7A	109.5
C2—N1—C6	121.01 (18)	C6—C7—H7B	109.5
C2—N1—C8	118.45 (19)	H7A—C7—H7B	109.5
C6—N1—C8	120.52 (19)	C6—C7—H7C	109.5
N1—C2—C3	119.9 (2)	H7A—C7—H7C	109.5
N1—C2—C9	119.51 (19)	H7B—C7—H7C	109.5
C3—C2—C9	120.6 (2)	N1—C8—H8A	109.5
C2—C3—C4	120.3 (2)	N1—C8—H8B	109.5
C2—C3—H3	119.9	H8A—C8—H8B	109.5
C4—C3—H3	119.9	N1—C8—H8C	109.5
O1—C4—C3	123.1 (2)	H8A—C8—H8C	109.5
O1—C4—C5	118.1 (2)	H8B—C8—H8C	109.5
C3—C4—C5	118.8 (2)	C2—C9—H9A	109.5
C6—C5—C4	120.1 (2)	C2—C9—H9B	109.5
C6—C5—H5	119.9	H9A—C9—H9B	109.5
C4—C5—H5	119.9	C2—C9—H9C	109.5
N1—C6—C5	119.8 (2)	H9A—C9—H9C	109.5
N1—C6—C7	119.5 (2)	H9B—C9—H9C	109.5
C6—N1—C2—C3	2.1 (3)	O1—C4—C5—C6	−179.7 (2)
C8—N1—C2—C3	−179.6 (2)	C3—C4—C5—C6	0.4 (3)
C6—N1—C2—C9	−178.86 (19)	C2—N1—C6—C5	−2.6 (3)
C8—N1—C2—C9	−0.6 (3)	C8—N1—C6—C5	179.2 (2)
N1—C2—C3—C4	−0.3 (3)	C2—N1—C6—C7	176.9 (2)
C9—C2—C3—C4	−179.33 (19)	C8—N1—C6—C7	−1.4 (3)
C2—C3—C4—O1	179.2 (2)	C4—C5—C6—N1	1.3 (3)
C2—C3—C4—C5	−1.0 (3)	C4—C5—C6—C7	−178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Wi	0.83 (2)	1.78 (2)	2.607 (2)	174 (3)
O1W—H1W···Br1	0.81 (2)	2.44 (2)	3.2407 (18)	170 (3)
O1W—H2W···Br1ii	0.83 (2)	2.43 (2)	3.2527 (18)	168 (3)
C3—H3···Br1i	0.95	2.86	3.785 (2)	164
C5—H5···Br1iii	0.95	2.90	3.837 (2)	170
C9—H9A···Br1iv	0.98	2.91	3.822 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1W i	0.83 (2)	1.78 (2)	2.607 (2)	174 (3)
O1W—H1W⋯Br1	0.81 (2)	2.44 (2)	3.2407 (18)	170 (3)
O1W—H2W⋯Br1ii	0.83 (2)	2.43 (2)	3.2527 (18)	168 (3)
C3—H3⋯Br1i	0.95	2.86	3.785 (2)	164
C5—H5⋯Br1iii	0.95	2.90	3.837 (2)	170
C9—H9A⋯Br1iv	0.98	2.91	3.822 (2)	155

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