8-Hy­droxy­quinolin-1-ium hydrogen sulfate monohydrate

Damous, M.; Dénès, G.; Bouacida, S.; Hamlaoui, M.; Merazig, H.; Daran, J.-C.

doi:10.1107/S1600536813022319

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages o1458-o1459

doi:10.1107/S1600536813022319

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8-Hydroxyquinolin-1-ium hydrogen sulfate monohydrate

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

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000, Algeria, ^bLaboratory of Solid State Chemistry and Mössbauer Spectroscopy, Laboratories for Inorganic Materials, Department of Chemistry and Biochemistry, Concordia University, Montreal, Quebec, H3G 1M8, Canada, ^cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria, and ^dLaboratoire de Chimie de Coordination, UPR CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 7 August 2013; accepted 8 August 2013; online 21 August 2013)

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 R₄⁴(12) rings and C₂²(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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.030
wR(F²) = 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

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) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

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).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536813022319/hg5339Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 standard bond lengths, see: Allen, (2002).

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. (Farrugia, 2012) The molecule structure of the title Compound with the atomic labelling scheme·Displacement are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. (Brandenburg & Berndt, 2001) A diagram of the layered crystal packing in (I), viewed down the a axis showing hydrogen bond as dashed line.
	Fig. 3. (Brandenburg & Berndt, 2001) Hydrogen bond connections as dashed line between hydrogenesulfate and water molecule building chain along the a axis.

8-Hydroxyquinolin-1-ium hydrogen sulfate monohydrate top

Crystal data top

C₉H₈NO⁺·HSO₄⁻·H₂O	Z = 2
M_r = 261.25	F(000) = 272
Triclinic, P1	D_x = 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

Data collection top

Agilent Xcalibur (Sapphire1) diffractometer	2171 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 8.2632 pixels mm^-1	θ_max = 26.4°, θ_min = 3.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
T_min = 0.874, T_max = 0.975	l = −14→14
10891 measured reflections

Refinement top

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(F_o²) + (0.0355P)² + 0.3301P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2171 reflections	Δρ_max = 0.41 e Å⁻³
163 parameters	Δρ_min = −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)

Crystal data top

C₉H₈NO⁺·HSO₄⁻·H₂O	γ = 105.712 (5)°
M_r = 261.25	V = 532.35 (5) Å³
Triclinic, P1	Z = 2
a = 6.5536 (4) Å	Mo Kα radiation
b = 8.0600 (5) Å	µ = 0.32 mm⁻¹
c = 11.3369 (6) Å	T = 180 K
α = 100.068 (5)°	0.43 × 0.16 × 0.08 mm
β = 106.344 (4)°

Data collection top

Agilent Xcalibur (Sapphire1) diffractometer	2171 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2000 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.975	R_int = 0.027
10891 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	3 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.41 e Å⁻³
2171 reflections	Δρ_min = −0.39 e Å⁻³
163 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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	0.849 (9)	1.888 (10)	2.7369 (17)	178.0 (2)
O1W—H2W···O14ⁱⁱ	0.853 (9)	2.031 (10)	2.8818 (19)	175.0 (2)
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) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1.

Acknowledgements

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.

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