8-Hy-droxy-5-(hy-droxy-meth-yl)quinolin-1-ium chloride.

The title compound, C(10)H(10)NO(2) (+)·Cl(-), contains a quinoline ring system which is essentially planar, with the largest deviation from the mean plane being 0.017 (1) Å. In the crystal, the ion pairs and their inversion-symmetry-related partners are linked by N-H⋯Cl and O-H⋯Cl hydrogen bonds to form tetramers which are further connected through O-H⋯O hydrogen bonds, building infinite one-dimensional chains parallel to the [010] direction.

Related literature

For anti­oxidant properties, see: Kayyali et al. (1998 ▶). For the synthesis of some substituted 8-quinolinol derivatives, see: Mishra et al. (2004 ▶). For the application of the corresponding aluminium complexes, see: Tang et al. (1989 ▶); Chen & Shi (1998 ▶); Shougen et al. (2000 ▶). For application as a promising display, see: Cao et al. (1996 ▶); Wu et al. (2003 ▶). For the synthesis, see: Zheng et al. (2005 ▶).

Experimental

Crystal data

C10H10NO2 +·Cl−

M = 211.64

Monoclinic,

a = 6.9081 (5) Å

b = 8.0577 (5) Å

c = 17.1890 (11) Å

β = 101.183 (3)°

V = 938.63 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.54 × 0.43 × 0.12 mm

Data collection

Bruker X8 APEX diffractometer

22727 measured reflections

4615 independent reflections

3679 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.124

S = 1.07

4615 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024233/fj2562sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024233/fj2562Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024233/fj2562Isup3.cml

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

C10H10NO2+·Cl−	F(000) = 440
Mr = 211.64	Dx = 1.498 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p_2ybc	Cell parameters from 4615 reflections
a = 6.9081 (5) Å	θ = 2.8–36.5°
b = 8.0577 (5) Å	µ = 0.38 mm−1
c = 17.1890 (11) Å	T = 296 K
β = 101.183 (3)°	Needle, colourless
V = 938.63 (11) Å3	0.54 × 0.43 × 0.12 mm
Z = 4

Bruker X8 APEX diffractometer	3679 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 36.5°, θmin = 2.8°
φ and ω scans	h = −11→11
22727 measured reflections	k = −12→13
4615 independent reflections	l = −28→28

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.124	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0694P)2 + 0.1142P] where P = (Fo2 + 2Fc2)/3
4615 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.16928 (4)	0.17354 (3)	0.310398 (15)	0.03843 (8)
O1	0.30276 (12)	0.22164 (9)	0.51946 (4)	0.03652 (16)
H1O	0.3342	0.1525	0.5547	0.055*
O2	0.44071 (12)	0.98428 (9)	0.61542 (5)	0.03859 (17)
H2O	0.5509	0.9455	0.6316	0.058*
N1	0.19725 (11)	0.47152 (9)	0.41916 (4)	0.02749 (14)
H1N	0.1996	0.3699	0.4041	0.033*
C1	0.14320 (16)	0.58746 (13)	0.36492 (5)	0.03366 (18)
H1	0.1075	0.5578	0.3118	0.040*
C2	0.13937 (16)	0.75383 (12)	0.38682 (6)	0.0362 (2)
H2	0.1026	0.8355	0.3486	0.043*
C3	0.19059 (14)	0.79558 (11)	0.46549 (6)	0.03077 (17)
H3	0.1887	0.9064	0.4804	0.037*
C4	0.24629 (12)	0.67260 (10)	0.52439 (5)	0.02444 (14)
C5	0.24952 (12)	0.50630 (10)	0.49814 (5)	0.02361 (14)
C6	0.30430 (13)	0.37354 (10)	0.55186 (5)	0.02688 (15)
C7	0.35081 (16)	0.40924 (12)	0.63135 (5)	0.03253 (18)
H7	0.3846	0.3239	0.6679	0.039*
C8	0.34767 (16)	0.57403 (12)	0.65797 (5)	0.03347 (18)
H8	0.3807	0.5948	0.7121	0.040*
C9	0.29775 (14)	0.70577 (11)	0.60713 (5)	0.02761 (15)
C10	0.29652 (17)	0.87978 (12)	0.63908 (6)	0.03501 (19)
H10A	0.1669	0.9279	0.6209	0.042*
H10B	0.3200	0.8753	0.6965	0.042*

	U11	U22	U33	U12	U13	U23
Cl1	0.04035 (14)	0.03721 (14)	0.03423 (12)	0.00236 (9)	−0.00147 (9)	−0.00972 (8)
O1	0.0523 (4)	0.0204 (3)	0.0344 (3)	0.0019 (3)	0.0024 (3)	0.0011 (2)
O2	0.0372 (4)	0.0224 (3)	0.0521 (4)	−0.0014 (2)	−0.0014 (3)	0.0061 (3)
N1	0.0306 (3)	0.0242 (3)	0.0260 (3)	−0.0013 (2)	0.0016 (2)	−0.0007 (2)
C1	0.0395 (5)	0.0317 (4)	0.0265 (4)	−0.0006 (3)	−0.0018 (3)	0.0027 (3)
C2	0.0431 (5)	0.0286 (4)	0.0326 (4)	0.0007 (4)	−0.0034 (4)	0.0066 (3)
C3	0.0334 (4)	0.0218 (3)	0.0342 (4)	0.0001 (3)	−0.0006 (3)	0.0035 (3)
C4	0.0243 (3)	0.0209 (3)	0.0274 (3)	−0.0018 (2)	0.0033 (3)	0.0011 (2)
C5	0.0242 (3)	0.0209 (3)	0.0251 (3)	−0.0015 (2)	0.0034 (2)	0.0013 (2)
C6	0.0304 (4)	0.0207 (3)	0.0289 (3)	−0.0018 (3)	0.0043 (3)	0.0028 (3)
C7	0.0432 (5)	0.0253 (4)	0.0277 (4)	−0.0024 (3)	0.0037 (3)	0.0053 (3)
C8	0.0450 (5)	0.0295 (4)	0.0254 (3)	−0.0046 (4)	0.0057 (3)	0.0009 (3)
C9	0.0317 (4)	0.0232 (3)	0.0280 (3)	−0.0040 (3)	0.0060 (3)	−0.0014 (3)
C10	0.0425 (5)	0.0263 (4)	0.0369 (4)	−0.0026 (3)	0.0094 (4)	−0.0061 (3)

O1—C6	1.3439 (11)	C3—H3	0.9300
O1—H1O	0.8200	C4—C5	1.4155 (11)
O2—C10	1.4225 (13)	C4—C9	1.4229 (12)
O2—H2O	0.8200	C5—C6	1.4158 (11)
N1—C1	1.3215 (12)	C6—C7	1.3721 (13)
N1—C5	1.3644 (11)	C7—C8	1.4059 (14)
N1—H1N	0.8600	C7—H7	0.9300
C1—C2	1.3941 (14)	C8—C9	1.3757 (13)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.3718 (14)	C9—C10	1.5065 (12)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.4155 (12)	C10—H10B	0.9700
C6—O1—H1O	109.5	C4—C5—C6	121.75 (7)
C10—O2—H2O	109.5	O1—C6—C7	125.81 (8)
C1—N1—C5	122.74 (8)	O1—C6—C5	115.99 (8)
C1—N1—H1N	118.6	C7—C6—C5	118.19 (8)
C5—N1—H1N	118.6	C6—C7—C8	120.44 (8)
N1—C1—C2	120.45 (9)	C6—C7—H7	119.8
N1—C1—H1	119.8	C8—C7—H7	119.8
C2—C1—H1	119.8	C9—C8—C7	122.67 (8)
C3—C2—C1	119.16 (8)	C9—C8—H8	118.7
C3—C2—H2	120.4	C7—C8—H8	118.7
C1—C2—H2	120.4	C8—C9—C4	118.25 (8)
C2—C3—C4	121.05 (8)	C8—C9—C10	120.34 (8)
C2—C3—H3	119.5	C4—C9—C10	121.41 (8)
C4—C3—H3	119.5	O2—C10—C9	113.14 (8)
C3—C4—C5	116.98 (8)	O2—C10—H10A	109.0
C3—C4—C9	124.33 (8)	C9—C10—H10A	109.0
C5—C4—C9	118.69 (7)	O2—C10—H10B	109.0
N1—C5—C4	119.60 (7)	C9—C10—H10B	109.0
N1—C5—C6	118.65 (7)	H10A—C10—H10B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1	0.86	2.24	3.0261 (8)	152
O1—H1O···O2i	0.82	1.78	2.5841 (10)	166
O2—H2O···Cl1ii	0.82	2.21	3.0281 (8)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1	0.86	2.24	3.0261 (8)	152
O1—H1O⋯O2i	0.82	1.78	2.5841 (10)	166
O2—H2O⋯Cl1ii	0.82	2.21	3.0281 (8)	172

Symmetry codes: (i) ; (ii) .