8-Hy­droxy­quinolin-1-ium hydrogen sulfate monohydrate

Maamar Damous; George Dénès; Sofiane Bouacida; Meriem Hamlaoui; Hocine Merazig; Jean-Claude Daran

doi:10.1107/S1600536813022319

. 2013 Aug 21;69(Pt 9):o1458–o1459. doi: 10.1107/S1600536813022319

8-Hydroxyquinolin-1-ium hydrogen sulfate monohydrate

Maamar Damous ^a, George Dénès ^b, Sofiane Bouacida ^a,^c,^*, Meriem Hamlaoui ^a, Hocine Merazig ^a, Jean-Claude Daran ^d

PMCID: PMC3884397 PMID: 24427083

Abstract

In the crystal structure of the title salt hydrate, C₉H₈NO⁺·HSO₄ ⁻·H₂O, the quinoline N—H atoms are hydrogen bonded to the bisulfate anions. The bisulfate anions and water molecules are linked together by O—H⋯O hydrogen-bonding interactions. 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 _r = 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
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-69-o1458-sup1.cif^{(22KB, cif)}

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

e-69-o1458-Isup2.hkl^{(104.5KB, hkl)}

Click here for additional data file.^{(4.4KB, cml)}

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

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

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

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

Acknowledgments

This work was supported by the Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, Algeria and Laboratoire de Chimie de Coordination Toulouse, France. Thanks are due to the Ministére de l’Enseignement Supérieur et de la Recherche Scientifique - Algérie (via the PNR project) for financial support.

supplementary crystallographic information

1. Comment

Recently, hydrogen-bonding patterns involving quinoline and its derivatives with organic acid have been investigated (Loh et al., 2010a,b). Syntheses of the quinoline derivatives were discussed earlier (Sasaki et al., 1998; Reux et al., 2009). Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991) and biologically active compounds (Markees et al., 1970). Herein we report the synthesis and crystal structure of 8-hydroxy-quinolin-1-ium hydrogen sulfate monohydrate (I). The molecular structure of (I), and the atomic numbering used, is illustrated in Fig. 1. The asymmetric unit of (I) consists of consists of one 8-hydroxy-quinolin-1-ium cation, one hydrogen sulfate anion and one water molecule. One proton is transferred from the hydroxyl group of sulfuric acid to the atom N1 of 8-hydroxy-quinoline during the crystallization, resulting in the formation of salt. All bond distances and angles are within the ranges of accepted values (CSD, Allen, 2002).

In the crystal structure, cationic and anionic layers alternate along the c axis and are linked by intermolecular N—H···O and O—H···O hydrogen bonds resulting in a two-dimensional network parallel to (100) (Table 1; Fig.2). Further O—H···O contacts connect these layers, forming a three-dimensional network in which R⁴₄(12) rings and C²₂(13) infinite chains are generated.

Perhaps the most interesting aspect of the structure results from the hydrogen bonding between the bisulfate anions and the solvent water molecule. This results in the formation of a ladder motif that runs parallel to the a axis (Fig. 3). Each bisulfate ion serves as a hydrogen bond donor to one water molecule and a hydrogen bond acceptor from a second water molecule forming the rails of the ladder, of form C²₂(6). The rungs are formed via a second water-donor/bisulfate acceptor pair, which generates rings within the ladder structure (two rungs and two rail sections in each ring), R⁴₄(12). There are two chemically different rings formed in this case since one involves rail sections with water molecules serving as the hydrogen bond donor and the other involves the bisulfate ion serving as the hydrogen bond donor.

2. Experimental

Single crystals of the compound C₉H₇NO⁺. HSO^-4. H₂O were grown as follows: 1 mmol of the copper sulfate pentahydrate CuSO₄. 5H₂O; 1 mmol of 8-hydroxy-quinoline and 1 mmol of sulfuric acid H₂SO₄ were mixed together in a minimum amount of distilled water. The clear solutions were stirred for 15 min and allowed to stand at room temperature. After a few days, Yellow crystals were formed. The product was filtered off, washed with a small amount of distilled water and was carefully isolated under polarizing microscope for analysis by X-ray diffraction.