8-Hy-droxy-5,7-dimethyl-quinolin-1-ium chloride dihydrate.

In the title hydrated salt, C11H12NO(+)·Cl(-)·2H2O, the quinoline ring system is essentially planar, with a maximum deviation of 0.005 (1) Å for all non-H atoms. In the crystal, the three components are linked by O-H⋯O, N-H⋯O, O-H⋯Cl and weak C-H⋯O hydrogen bonds, forming a layer structure parallel to the ac plane. The crystal structure is further stabilized by π-π stacking inter-actions, with centroid-centroid distances of 3.5213 (6) and 3.7176 (6) Å.

Related literature

For background to and the biological activity of quinoline derivatives, see: Balasubramanian & Muthiah (1996a ▶,b ▶); Morimoto et al. (1991 ▶); Markees et al. (1970 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H12NO+·Cl−·2H2O

M = 245.70

Triclinic,

a = 6.7990 (5) Å

b = 9.2215 (6) Å

c = 10.2123 (7) Å

α = 103.820 (1)°

β = 95.629 (1)°

γ = 105.517 (1)°

V = 590.04 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.38 × 0.20 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.958

9368 measured reflections

3410 independent reflections

3153 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.092

S = 1.08

3410 reflections

171 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049495/is5226sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049495/is5226Isup2.hkl

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

C11H12NO+·Cl−·2H2O	Z = 2
Mr = 245.70	F(000) = 260
Triclinic, P1	Dx = 1.383 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7990 (5) Å	Cell parameters from 6250 reflections
b = 9.2215 (6) Å	θ = 2.7–30.1°
c = 10.2123 (7) Å	µ = 0.32 mm−1
α = 103.820 (1)°	T = 100 K
β = 95.629 (1)°	Block, yellow
γ = 105.517 (1)°	0.38 × 0.20 × 0.14 mm
V = 590.04 (7) Å3

Bruker APEXII DUO CCD area-detector diffractometer	3410 independent reflections
Radiation source: fine-focus sealed tube	3153 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.889, Tmax = 0.958	k = −12→12
9368 measured reflections	l = −14→14

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.058P)2 + 0.1137P] where P = (Fo2 + 2Fc2)/3
3410 reflections	(Δ/σ)max = 0.001
171 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.22874 (4)	0.70417 (3)	0.91682 (2)	0.01867 (8)
O1W	0.49841 (12)	0.45266 (8)	0.25460 (7)	0.01707 (15)
O1	0.34288 (12)	0.31466 (8)	0.43983 (7)	0.01753 (15)
O2W	0.22470 (13)	0.42047 (10)	1.03561 (8)	0.02223 (16)
N1	0.35726 (12)	0.22535 (9)	0.66748 (8)	0.01260 (15)
C1	0.36928 (14)	0.19382 (11)	0.78767 (9)	0.01493 (17)
H1A	0.4133	0.2770	0.8699	0.018*
C2	0.31746 (15)	0.03900 (11)	0.79353 (9)	0.01541 (17)
H2A	0.3259	0.0159	0.8793	0.018*
C3	0.25385 (14)	−0.08005 (11)	0.67341 (9)	0.01452 (17)
H3A	0.2176	−0.1858	0.6769	0.017*
C4	0.24166 (13)	−0.04734 (10)	0.54510 (9)	0.01229 (16)
C5	0.17880 (14)	−0.16484 (10)	0.41697 (9)	0.01365 (17)
C6	0.17410 (14)	−0.11634 (10)	0.29989 (9)	0.01398 (17)
H6A	0.1328	−0.1942	0.2143	0.017*
C7	0.22731 (13)	0.04326 (10)	0.29896 (9)	0.01296 (17)
C8	0.29038 (13)	0.15788 (10)	0.42249 (9)	0.01246 (16)
C9	0.29632 (13)	0.11195 (10)	0.54492 (9)	0.01168 (16)
C10	0.11810 (16)	−0.33626 (11)	0.41114 (10)	0.01908 (19)
H10A	0.0812	−0.3994	0.3153	0.029*
H10B	−0.0012	−0.3613	0.4573	0.029*
H10C	0.2348	−0.3595	0.4569	0.029*
C11	0.21195 (15)	0.08368 (11)	0.16520 (9)	0.01676 (18)
H11A	0.1307	0.1572	0.1680	0.025*
H11B	0.1439	−0.0118	0.0908	0.025*
H11C	0.3513	0.1320	0.1494	0.025*
H1N1	0.389 (3)	0.318 (2)	0.6664 (18)	0.037 (4)*
H2W1	0.584 (3)	0.411 (2)	0.2240 (19)	0.040 (5)*
H2W2	0.228 (3)	0.497 (2)	1.001 (2)	0.050 (5)*
H1O1	0.385 (3)	0.347 (2)	0.3707 (19)	0.038 (4)*
H1W2	0.115 (3)	0.390 (2)	1.0495 (18)	0.036 (4)*
H1W1	0.416 (3)	0.446 (2)	0.1895 (19)	0.038 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02078 (13)	0.01844 (12)	0.01979 (13)	0.00704 (9)	0.00619 (9)	0.00844 (9)
O1W	0.0219 (3)	0.0155 (3)	0.0134 (3)	0.0053 (3)	0.0038 (3)	0.0035 (2)
O1	0.0275 (4)	0.0127 (3)	0.0126 (3)	0.0050 (3)	0.0048 (3)	0.0046 (2)
O2W	0.0205 (4)	0.0251 (4)	0.0262 (4)	0.0094 (3)	0.0057 (3)	0.0130 (3)
N1	0.0138 (3)	0.0131 (3)	0.0105 (3)	0.0039 (3)	0.0020 (3)	0.0027 (3)
C1	0.0157 (4)	0.0183 (4)	0.0103 (4)	0.0050 (3)	0.0021 (3)	0.0032 (3)
C2	0.0165 (4)	0.0192 (4)	0.0119 (4)	0.0058 (3)	0.0029 (3)	0.0061 (3)
C3	0.0146 (4)	0.0160 (4)	0.0143 (4)	0.0048 (3)	0.0033 (3)	0.0061 (3)
C4	0.0112 (4)	0.0142 (4)	0.0120 (4)	0.0044 (3)	0.0021 (3)	0.0040 (3)
C5	0.0134 (4)	0.0131 (4)	0.0140 (4)	0.0040 (3)	0.0025 (3)	0.0029 (3)
C6	0.0140 (4)	0.0147 (4)	0.0118 (4)	0.0040 (3)	0.0019 (3)	0.0015 (3)
C7	0.0123 (4)	0.0158 (4)	0.0110 (4)	0.0046 (3)	0.0022 (3)	0.0038 (3)
C8	0.0133 (4)	0.0134 (4)	0.0114 (4)	0.0044 (3)	0.0028 (3)	0.0041 (3)
C9	0.0108 (3)	0.0142 (4)	0.0100 (4)	0.0041 (3)	0.0022 (3)	0.0028 (3)
C10	0.0241 (5)	0.0128 (4)	0.0187 (4)	0.0039 (3)	0.0031 (4)	0.0033 (3)
C11	0.0208 (4)	0.0188 (4)	0.0100 (4)	0.0052 (3)	0.0015 (3)	0.0040 (3)

O1W—H2W1	0.828 (19)	C4—C9	1.4160 (12)
O1W—H1W1	0.806 (19)	C4—C5	1.4262 (12)
O1—C8	1.3558 (11)	C5—C6	1.3735 (12)
O1—H1O1	0.873 (19)	C5—C10	1.5079 (13)
O2W—H2W2	0.86 (2)	C6—C7	1.4211 (12)
O2W—H1W2	0.76 (2)	C6—H6A	0.9500
N1—C1	1.3271 (11)	C7—C8	1.3809 (12)
N1—C9	1.3686 (11)	C7—C11	1.5006 (12)
N1—H1N1	0.828 (19)	C8—C9	1.4129 (12)
C1—C2	1.3935 (13)	C10—H10A	0.9800
C1—H1A	0.9500	C10—H10B	0.9800
C2—C3	1.3768 (13)	C10—H10C	0.9800
C2—H2A	0.9500	C11—H11A	0.9800
C3—C4	1.4127 (12)	C11—H11B	0.9800
C3—H3A	0.9500	C11—H11C	0.9800
H2W1—O1W—H1W1	106.5 (17)	C7—C6—H6A	118.0
C8—O1—H1O1	116.0 (11)	C8—C7—C6	118.69 (8)
H2W2—O2W—H1W2	107.8 (19)	C8—C7—C11	121.56 (8)
C1—N1—C9	123.25 (8)	C6—C7—C11	119.75 (8)
C1—N1—H1N1	118.5 (12)	O1—C8—C7	126.20 (8)
C9—N1—H1N1	118.2 (12)	O1—C8—C9	115.02 (8)
N1—C1—C2	120.13 (8)	C7—C8—C9	118.75 (8)
N1—C1—H1A	119.9	N1—C9—C8	118.85 (8)
C2—C1—H1A	119.9	N1—C9—C4	118.90 (8)
C3—C2—C1	119.17 (8)	C8—C9—C4	122.25 (8)
C3—C2—H2A	120.4	C5—C10—H10A	109.5
C1—C2—H2A	120.4	C5—C10—H10B	109.5
C2—C3—C4	121.00 (8)	H10A—C10—H10B	109.5
C2—C3—H3A	119.5	C5—C10—H10C	109.5
C4—C3—H3A	119.5	H10A—C10—H10C	109.5
C3—C4—C9	117.54 (8)	H10B—C10—H10C	109.5
C3—C4—C5	123.88 (8)	C7—C11—H11A	109.5
C9—C4—C5	118.58 (8)	C7—C11—H11B	109.5
C6—C5—C4	117.73 (8)	H11A—C11—H11B	109.5
C6—C5—C10	121.45 (8)	C7—C11—H11C	109.5
C4—C5—C10	120.82 (8)	H11A—C11—H11C	109.5
C5—C6—C7	123.99 (8)	H11B—C11—H11C	109.5
C5—C6—H6A	118.0
C9—N1—C1—C2	−0.37 (14)	C11—C7—C8—O1	0.57 (14)
N1—C1—C2—C3	−0.04 (14)	C6—C7—C8—C9	−1.01 (13)
C1—C2—C3—C4	0.35 (14)	C11—C7—C8—C9	178.35 (8)
C2—C3—C4—C9	−0.27 (13)	C1—N1—C9—C8	−179.47 (8)
C2—C3—C4—C5	179.45 (8)	C1—N1—C9—C4	0.44 (13)
C3—C4—C5—C6	−179.96 (8)	O1—C8—C9—N1	−1.49 (12)
C9—C4—C5—C6	−0.25 (12)	C7—C8—C9—N1	−179.51 (8)
C3—C4—C5—C10	0.53 (13)	O1—C8—C9—C4	178.60 (8)
C9—C4—C5—C10	−179.75 (8)	C7—C8—C9—C4	0.59 (13)
C4—C5—C6—C7	−0.21 (13)	C3—C4—C9—N1	−0.12 (12)
C10—C5—C6—C7	179.30 (8)	C5—C4—C9—N1	−179.85 (8)
C5—C6—C7—C8	0.86 (14)	C3—C4—C9—C8	179.79 (8)
C5—C6—C7—C11	−178.51 (9)	C5—C4—C9—C8	0.06 (13)
C6—C7—C8—O1	−178.78 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2W	0.95	2.55	3.2871 (13)	134
O2W—H2W2···Cl1	0.858 (19)	2.274 (19)	3.1306 (10)	177.4 (18)
O1—H1O1···O1W	0.874 (19)	1.811 (19)	2.6718 (10)	167.9 (18)
N1—H1N1···O1Wi	0.826 (18)	1.977 (18)	2.7516 (11)	155.9 (17)
O1W—H2W1···Cl1i	0.83 (2)	2.27 (2)	3.0758 (9)	164.0 (18)
O2W—H1W2···Cl1ii	0.76 (2)	2.36 (2)	3.1187 (10)	177.7 (18)
O1W—H1W1···O2Wiii	0.805 (19)	1.86 (2)	2.6690 (11)	177.2 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2W	0.95	2.55	3.2871 (13)	134
O2W—H2W2⋯Cl1	0.858 (19)	2.274 (19)	3.1306 (10)	177.4 (18)
O1—H1O1⋯O1W	0.874 (19)	1.811 (19)	2.6718 (10)	167.9 (18)
N1—H1N1⋯O1W i	0.826 (18)	1.977 (18)	2.7516 (11)	155.9 (17)
O1W—H2W1⋯Cl1i	0.83 (2)	2.27 (2)	3.0758 (9)	164.0 (18)
O2W—H1W2⋯Cl1ii	0.76 (2)	2.36 (2)	3.1187 (10)	177.7 (18)
O1W—H1W1⋯O2W iii	0.805 (19)	1.86 (2)	2.6690 (11)	177.2 (19)

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