8-Hy-droxy-quinolin-1-ium hydrogen sulfate monohydrate.

In the crystal structure of the title salt hydrate, C9H8NO(+)·HSO4 (-)·H2O, the quinoline N-H atoms are hydrogen bonded to the bis-ulfate anions. The bis-ulfate anions and water mol-ecules are linked together by O-H⋯O hydrogen-bonding inter-actions. The cations and anions form separate layers alternating along the c axis, which are linked by N-H⋯O and O-H⋯O hydrogen bonds into a two-dimensional network parallel to (100). Further O-H⋯O contacts connect these layers, forming a three-dimensional network, in which two R 4 (4)(12) rings and C 2 (2)(13) infinite chains can be identified.

Related literature

For background to and the biological activity of quinoline derivatives, see: Sasaki et al. (1998 ▶); Reux et al. (2009 ▶); Morimoto et al. (1991 ▶); Markees et al. (1970 ▶). For related structures, see: Loh et al. (2010a ▶,b ▶). For a description of the Cambridge Structural Database, see: Allen, (2002 ▶).

Experimental

Crystal data

C9H8NO+·HSO4 −·H2O

M = 261.25

Triclinic,

a = 6.5536 (4) Å

b = 8.0600 (5) Å

c = 11.3369 (6) Å

α = 100.068 (5)°

β = 106.344 (4)°

γ = 105.712 (5)°

V = 532.35 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 180 K

0.43 × 0.16 × 0.08 mm

Data collection

Agilent Xcalibur (Sapphire1) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.874, T max = 0.975

10891 measured reflections

2171 independent reflections

2000 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.05

2171 reflections

163 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813022319/hg5339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022319/hg5339Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022319/hg5339Isup3.cml

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

C9H8NO+·HSO4−·H2O	Z = 2
Mr = 261.25	F(000) = 272
Triclinic, P1	Dx = 1.63 Mg m−3
a = 6.5536 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0600 (5) Å	Cell parameters from 8303 reflections
c = 11.3369 (6) Å	θ = 3.3–28.4°
α = 100.068 (5)°	µ = 0.32 mm−1
β = 106.344 (4)°	T = 180 K
γ = 105.712 (5)°	Box, yellow
V = 532.35 (5) Å3	0.43 × 0.16 × 0.08 mm

Agilent Xcalibur (Sapphire1) diffractometer	2171 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.2632 pixels mm-1	θmax = 26.4°, θmin = 3.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
Tmin = 0.874, Tmax = 0.975	l = −14→14
10891 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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0355P)2 + 0.3301P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2171 reflections	Δρmax = 0.41 e Å−3
163 parameters	Δρmin = −0.39 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: 0.064 (4)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies, 2011)

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
C2	0.0574 (3)	−0.1138 (2)	0.22102 (15)	0.0278 (3)
H2	0.0132	−0.0941	0.1388	0.033*
C3	0.0242 (3)	−0.2869 (2)	0.23249 (16)	0.0322 (4)
H3	−0.0426	−0.3858	0.1584	0.039*
C4	0.0881 (3)	−0.3137 (2)	0.35064 (17)	0.0295 (4)
H4	0.0666	−0.432	0.3587	0.035*
C5	0.1857 (2)	−0.1681 (2)	0.46135 (15)	0.0227 (3)
C6	0.2554 (3)	−0.1860 (2)	0.58640 (16)	0.0284 (3)
H6	0.2366	−0.3013	0.6001	0.034*
C7	0.3500 (3)	−0.0372 (2)	0.68755 (15)	0.0286 (4)
H7	0.3962	−0.0503	0.7717	0.034*
C8	0.3810 (2)	0.1351 (2)	0.67071 (14)	0.0248 (3)
H8	0.4469	0.2363	0.7432	0.03*
C9	0.3169 (2)	0.15841 (19)	0.55040 (14)	0.0204 (3)
C10	0.2174 (2)	0.00521 (19)	0.44474 (13)	0.0193 (3)
N1	0.1504 (2)	0.02392 (17)	0.32431 (11)	0.0213 (3)
H1	0.1697	0.1324	0.3146	0.026*
O1W	0.6635 (2)	0.23721 (17)	0.01309 (13)	0.0362 (3)
H1W	0.686 (4)	0.329 (2)	−0.015 (2)	0.054*
H2W	0.788 (2)	0.246 (3)	0.0684 (18)	0.054*
O9	0.34231 (19)	0.31692 (14)	0.52328 (10)	0.0270 (3)
H9	0.402	0.3998	0.5915	0.04*
O11	0.2516 (2)	0.46432 (17)	0.07413 (12)	0.0396 (3)
O12	0.30658 (19)	0.17896 (15)	0.07153 (11)	0.0303 (3)
H12	0.4287	0.2071	0.0572	0.045*
O13	0.4983 (2)	0.42607 (17)	0.26039 (11)	0.0384 (3)
O14	0.0966 (2)	0.27484 (17)	0.19066 (13)	0.0371 (3)
S1	0.28858 (6)	0.34687 (5)	0.15279 (3)	0.02286 (14)

	U11	U22	U33	U12	U13	U23
C2	0.0232 (7)	0.0338 (8)	0.0216 (7)	0.0084 (6)	0.0056 (6)	0.0013 (6)
C3	0.0266 (8)	0.0275 (8)	0.0324 (9)	0.0050 (6)	0.0078 (7)	−0.0056 (7)
C4	0.0244 (8)	0.0212 (7)	0.0424 (10)	0.0075 (6)	0.0133 (7)	0.0051 (7)
C5	0.0172 (7)	0.0231 (7)	0.0309 (8)	0.0085 (6)	0.0107 (6)	0.0089 (6)
C6	0.0255 (8)	0.0303 (8)	0.0385 (9)	0.0140 (6)	0.0141 (7)	0.0193 (7)
C7	0.0239 (8)	0.0431 (9)	0.0263 (8)	0.0161 (7)	0.0101 (6)	0.0177 (7)
C8	0.0197 (7)	0.0319 (8)	0.0204 (7)	0.0078 (6)	0.0060 (6)	0.0044 (6)
C9	0.0157 (7)	0.0225 (7)	0.0231 (7)	0.0065 (5)	0.0070 (5)	0.0055 (6)
C10	0.0146 (6)	0.0227 (7)	0.0212 (7)	0.0067 (5)	0.0066 (5)	0.0059 (6)
N1	0.0197 (6)	0.0226 (6)	0.0208 (6)	0.0073 (5)	0.0061 (5)	0.0055 (5)
O1W	0.0411 (7)	0.0315 (7)	0.0434 (8)	0.0157 (6)	0.0188 (6)	0.0159 (6)
O9	0.0332 (6)	0.0193 (5)	0.0230 (5)	0.0053 (4)	0.0067 (5)	0.0033 (4)
O11	0.0560 (8)	0.0384 (7)	0.0367 (7)	0.0252 (6)	0.0170 (6)	0.0241 (6)
O12	0.0311 (6)	0.0242 (6)	0.0311 (6)	0.0096 (5)	0.0086 (5)	−0.0001 (5)
O13	0.0405 (7)	0.0353 (7)	0.0282 (6)	0.0176 (6)	−0.0021 (5)	−0.0028 (5)
O14	0.0411 (7)	0.0367 (7)	0.0459 (7)	0.0182 (6)	0.0242 (6)	0.0187 (6)
S1	0.0289 (2)	0.0205 (2)	0.0203 (2)	0.01131 (15)	0.00646 (15)	0.00689 (14)

C2—N1	1.324 (2)	C8—H8	0.95
C2—C3	1.387 (2)	C9—O9	1.3437 (18)
C2—H2	0.95	C9—C10	1.411 (2)
C3—C4	1.360 (3)	C10—N1	1.3602 (19)
C3—H3	0.95	N1—H1	0.88
C4—C5	1.410 (2)	O1W—H1W	0.849 (9)
C4—H4	0.95	O1W—H2W	0.853 (9)
C5—C6	1.408 (2)	O9—H9	0.84
C5—C10	1.410 (2)	O11—S1	1.4310 (12)
C6—C7	1.362 (2)	O12—S1	1.5511 (11)
C6—H6	0.95	O12—H12	0.84
C7—C8	1.402 (2)	O13—S1	1.4467 (12)
C7—H7	0.95	O14—S1	1.4491 (12)
C8—C9	1.372 (2)
N1—C2—C3	120.19 (15)	C7—C8—H8	119.7
N1—C2—H2	119.9	O9—C9—C8	125.44 (14)
C3—C2—H2	119.9	O9—C9—C10	116.15 (13)
C4—C3—C2	119.46 (15)	C8—C9—C10	118.41 (14)
C4—C3—H3	120.3	N1—C10—C5	118.99 (13)
C2—C3—H3	120.3	N1—C10—C9	119.78 (13)
C3—C4—C5	120.84 (15)	C5—C10—C9	121.23 (14)
C3—C4—H4	119.6	C2—N1—C10	122.93 (14)
C5—C4—H4	119.6	C2—N1—H1	118.5
C6—C5—C10	118.55 (14)	C10—N1—H1	118.5
C6—C5—C4	123.86 (15)	H1W—O1W—H2W	108.3 (17)
C10—C5—C4	117.58 (14)	C9—O9—H9	109.5
C7—C6—C5	119.63 (15)	S1—O12—H12	109.5
C7—C6—H6	120.2	O11—S1—O13	112.76 (8)
C5—C6—H6	120.2	O11—S1—O14	112.44 (8)
C6—C7—C8	121.68 (14)	O13—S1—O14	112.45 (8)
C6—C7—H7	119.2	O11—S1—O12	108.35 (7)
C8—C7—H7	119.2	O13—S1—O12	106.44 (7)
C9—C8—C7	120.50 (14)	O14—S1—O12	103.72 (7)
C9—C8—H8	119.7
N1—C2—C3—C4	0.0 (2)	C4—C5—C10—N1	0.9 (2)
C2—C3—C4—C5	0.5 (2)	C6—C5—C10—C9	0.1 (2)
C3—C4—C5—C6	179.92 (14)	C4—C5—C10—C9	−179.10 (13)
C3—C4—C5—C10	−0.9 (2)	O9—C9—C10—N1	−1.08 (19)
C10—C5—C6—C7	0.3 (2)	C8—C9—C10—N1	179.47 (12)
C4—C5—C6—C7	179.42 (14)	O9—C9—C10—C5	178.89 (12)
C5—C6—C7—C8	−0.2 (2)	C8—C9—C10—C5	−0.6 (2)
C6—C7—C8—C9	−0.3 (2)	C3—C2—N1—C10	0.0 (2)
C7—C8—C9—O9	−178.76 (14)	C5—C10—N1—C2	−0.4 (2)
C7—C8—C9—C10	0.6 (2)	C9—C10—N1—C2	179.54 (13)
C6—C5—C10—N1	−179.92 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O14	0.88	2.00	2.7690 (18)	145
O1W—H1W···O11i	0.85 (1)	1.89 (1)	2.7369 (17)	178 (1)
O1W—H2W···O14ii	0.85 (1)	2.03 (1)	2.8818 (19)	175 (1)
O9—H9···O13iii	0.84	1.81	2.6470 (16)	174
O12—H12···O1W	0.84	1.72	2.5529 (17)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O14	0.88	2.00	2.7690 (18)	145
O1W—H1W⋯O11i	0.85 (1)	1.89 (1)	2.7369 (17)	178 (1)
O1W—H2W⋯O14ii	0.85 (1)	2.03 (1)	2.8818 (19)	175 (1)
O9—H9⋯O13iii	0.84	1.81	2.6470 (16)	174
O12—H12⋯O1W	0.84	1.72	2.5529 (17)	172

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