
==== Front
IUCrdata
IUCrdata
IUCrData
IUCrData
2414-3146
International Union of Crystallography

wm4218
10.1107/S2414314624008265
IUCRBK
S2414314624008265
Data Reports
Bis(2-carb­oxy­quinolinium) hexa­chlorido­stan­nate(IV) dihydrate
(C10H8NO2)[SnCl6]·2H2O
Benhamada Mohamed Siradj Eddine a*
Benlatreche Tarek a
Ghallab Rochdi b
Dénès George c
Merazig Hocine a
a https://ror.org/017wv6808 Environmental Molecular and Structural Chemistry Research Unit University of Constantine-1 25000 Constantine Algeria
b https://ror.org/05t0zwy08 Ecole Nationale Polytechnique de Constantine (ENPC) Laboratoire de Technologie des Matériaux Avancés Algeria
c Laboratory of Solid State Chemistry and Mössbauer Spectroscopy, Department of Chemistry and Biochemistry, Concordia University, 7141 Sherbrooke St. West, Monreal, H4B 1R6 QC, Canada
Weil M. Editor
Vienna University of Technology, Austria
Correspondence e-mail: mbenhamada@hotmail.fr
8 2024
30 8 2024
30 8 2024
9 Pt 8 x240800 x24082608 7 2024
21 8 2024
© Benhamada et al. 2024
2024
https://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A full version of this article is available from Crystallography Journals Online.
In the title compound, the 2-carb­oxy­quinolinium cation, the [SnCl6]2– anion (site symmetry ) and the water mol­ecule of crystallization are held together by hydrogen bonds, π–π stacking and C—Cl⋯π inter­actions.

In the hydrated title salt, (C10H8NO2)2[SnCl6]·2H2O, the tin(IV) atom is located about a center of inversion. In the crystal structure, the organic cation, the octa­hedral inorganic anion and the water mol­ecule of crystallization inter­act through O—H⋯O, N—H⋯O and O—H⋯Cl hydrogen bonds, supplemented by weak π–π stacking between neighboring cations, and C—Cl⋯π inter­actions.

crystal structure
[SnCl6]2– anion
hydrogen-bonding
π–π stacking
==== Body
pmcStructure description

The crystal structure determination of the title compound, (I), was undertaken as part of studies of organic–inorganic hybrid materials, which may exhibit various inter­esting physical properties such as dielectric characteristics (Hajlaoui et al., 2013 ▸).

The asymmetric unit of (I) comprises half of an octa­hedral [SnCl6]2– anion (the whole anion being completed by inversion symmetry), one 2-carb­oxy­quinolinium cation, and a water mol­ecule of crystallization (Fig. 1 ▸).

The SnIV atom is coordinated by six chlorine atoms, forming a slightly distorted octa­hedron. The lengths of the Sn—Cl bonds in the hexa­chlorido­stannate(IV) anion range from 2.4180 (3) to 2.4406 (3) Å and the Cl—Sn—Cl bond angles deviate only by approximately 1° from ideal values, similar to those reported in the literature (Ghallab et al., 2020 ▸; Rademeyer, 2004 ▸; Billing et al., 2007 ▸).

In the 2-carb­oxy­quinolinium cation, the C—C bond lengths range from 1.364 (2) to 1.5029 (15) Å and the C—N bond lengths are 1.3282 (14) and 1.3649 (17) Å; the angles vary between 115.14 (10) (N1—C2—C1) and 126.71 (11)° (O1—C—O2). These values are similar compared with related cations with protonated aromatic N atoms (Gelmboldt et al., 2007 ▸; Smith et al., 2004 ▸, 2008 ▸). The cation in (I) is not planar, as indicated by a dihedral angle between the quinoline ring and the carb­oxy group of 11.61 (9)°.

Apart from Coulombic forces, the cohesion in the crystal structure is ensured by classical hydrogen bonds between the carboxyl group as donor and the water mol­ecule as acceptor groups, and by inter­actions between the protonated quinoline N atom and the non-protonated O atom of the carboxyl group of a neighboring mol­ecule. Further inter­actions involve the water mol­ecule and the hexa­chlorido­stannate anion (Table 1 ▸, Fig. 2 ▸). There are also π–π stacking inter­actions between neighboring cations [3.7898 (8) Å, slippage 1.678 Å; Fig. 3 ▸a] and Cl⋯π inter­actions [3.5633 (6) Å; Fig. 3 ▸b].

Synthesis and crystallization

Tin(II) chloride dihydrate (SnCl2·2H2O) was mixed with quinaldic acid (C10H7NO2) in a 1:2 molar ratio, along with a few drops of hydro­chloric acid in distilled water. The mixture was refluxed for one h at 343 K. After two weeks of slow solvent evaporation at room temperature, colorless single crystals suitable for X-ray analysis were obtained.

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 2 ▸. The H atom bound to the N atom was refined freely. 14 reflections were omitted from the refinement because they were obstructed from the beam stop.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624008265/wm4218sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624008265/wm4218Isup4.hkl

CCDC reference: 2378953

Additional supporting information: crystallographic information; 3D view; checkCIF report

Thanks are due to DRSDT-Algeria.

full crystallographic data

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Crystal data

(C10H8NO2)[SnCl6]·2H2O	Z = 1	
Mr = 715.77	F(000) = 354	
Triclinic, P1	Dx = 1.794 Mg m−3	
a = 8.3220 (4) Å	Mo Kα radiation, λ = 0.71073 Å	
b = 9.2704 (4) Å	Cell parameters from 9611 reflections	
c = 9.4248 (4) Å	θ = 3.7–48.2°	
α = 108.101 (2)°	µ = 1.61 mm−1	
β = 99.515 (2)°	T = 296 K	
γ = 99.749 (2)°	Plate, yellow	
V = 662.46 (5) Å3	0.10 × 0.09 × 0.08 mm	

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Data collection

Bruker APEXII CCD diffractometer	3199 reflections with I > 2σ(I)	
φ and ω scans	Rint = 0.015	
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 28.3°, θmin = 4.8°	
Tmin = 0.851, Tmax = 0.879	h = −11→11	
19467 measured reflections	k = −12→12	
3262 independent reflections	l = −12→12	

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Refinement

Refinement on F2	0 restraints	
Least-squares matrix: full	Hydrogen site location: mixed	
R[F2 > 2σ(F2)] = 0.013	H atoms treated by a mixture of independent and constrained refinement	
wR(F2) = 0.033	w = 1/[σ2(Fo2) + (0.013P)2 + 0.3169P] where P = (Fo2 + 2Fc2)/3	
S = 1.08	(Δ/σ)max < 0.001	
3262 reflections	Δρmax = 0.41 e Å−3	
168 parameters	Δρmin = −0.25 e Å−3	

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.	

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

	x	y	z	Uiso*/Ueq		
Sn1	0.000000	0.000000	0.000000	0.01307 (3)		
Cl1	0.12549 (3)	0.26567 (3)	0.17700 (3)	0.01985 (6)		
Cl2	−0.27553 (3)	0.05974 (3)	−0.01450 (3)	0.02261 (6)		
Cl3	−0.03577 (4)	−0.08014 (3)	0.21592 (3)	0.02122 (6)		
O2	0.82893 (11)	0.48826 (10)	0.04894 (9)	0.02362 (17)		
O1	0.70770 (11)	0.47285 (12)	0.24138 (10)	0.02734 (19)		
H1	0.625567	0.421382	0.171718	0.041*		
O3	0.44565 (12)	0.30407 (12)	0.03220 (12)	0.0316 (2)		
H3A	0.358189	0.328438	0.058776	0.047*		
H3B	0.438485	0.207555	0.016123	0.047*		
N1	1.12611 (12)	0.62982 (11)	0.25392 (11)	0.01629 (17)		
C2	0.98812 (14)	0.60663 (12)	0.30529 (12)	0.0171 (2)		
C1	0.83151 (14)	0.51554 (13)	0.18355 (13)	0.0183 (2)		
C3	0.99422 (16)	0.66408 (14)	0.46178 (13)	0.0213 (2)		
H3	0.897184	0.649793	0.497561	0.026*		
C6	1.28072 (14)	0.70531 (13)	0.34788 (13)	0.0181 (2)		
C9	1.59120 (17)	0.85434 (15)	0.54706 (16)	0.0299 (3)		
H9	1.696466	0.902964	0.612341	0.036*		
C8	1.57523 (16)	0.79829 (15)	0.38631 (16)	0.0277 (3)		
H8	1.670263	0.812255	0.347661	0.033*		
C7	1.42258 (15)	0.72382 (14)	0.28635 (14)	0.0230 (2)		
H7	1.413118	0.686630	0.180899	0.028*		
C5	1.29308 (15)	0.76284 (13)	0.50879 (13)	0.0208 (2)		
C10	1.45388 (17)	0.83779 (15)	0.60721 (14)	0.0274 (3)		
H10	1.465775	0.875747	0.712974	0.033*		
C4	1.14626 (16)	0.74234 (14)	0.56255 (13)	0.0230 (2)		
H4	1.151849	0.782030	0.667260	0.028*		
H1A	1.119 (2)	0.5947 (19)	0.160 (2)	0.026 (4)*		

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Atomic displacement parameters (Å2)

	U11	U22	U33	U12	U13	U23	
Sn1	0.01189 (5)	0.01279 (5)	0.01377 (5)	0.00232 (3)	0.00262 (3)	0.00407 (4)	
Cl1	0.02182 (13)	0.01429 (11)	0.01922 (12)	0.00029 (9)	0.00555 (10)	0.00173 (9)	
Cl2	0.01509 (12)	0.02717 (14)	0.02324 (13)	0.00878 (10)	0.00250 (10)	0.00457 (11)	
Cl3	0.02591 (13)	0.02106 (13)	0.01886 (12)	0.00433 (10)	0.00618 (10)	0.01006 (10)	
O2	0.0205 (4)	0.0291 (4)	0.0164 (4)	0.0005 (3)	0.0033 (3)	0.0045 (3)	
O1	0.0201 (4)	0.0358 (5)	0.0226 (4)	−0.0002 (4)	0.0071 (3)	0.0077 (4)	
O3	0.0207 (4)	0.0325 (5)	0.0368 (5)	−0.0007 (4)	0.0106 (4)	0.0069 (4)	
N1	0.0185 (4)	0.0158 (4)	0.0123 (4)	0.0036 (3)	0.0020 (3)	0.0028 (3)	
C2	0.0197 (5)	0.0152 (5)	0.0164 (5)	0.0049 (4)	0.0035 (4)	0.0053 (4)	
C1	0.0182 (5)	0.0175 (5)	0.0187 (5)	0.0047 (4)	0.0046 (4)	0.0051 (4)	
C3	0.0257 (6)	0.0217 (5)	0.0175 (5)	0.0074 (4)	0.0075 (4)	0.0063 (4)	
C6	0.0196 (5)	0.0150 (5)	0.0167 (5)	0.0038 (4)	0.0005 (4)	0.0037 (4)	
C9	0.0239 (6)	0.0260 (6)	0.0301 (6)	0.0012 (5)	−0.0089 (5)	0.0069 (5)	
C8	0.0201 (6)	0.0267 (6)	0.0330 (7)	0.0044 (5)	0.0023 (5)	0.0084 (5)	
C7	0.0210 (6)	0.0235 (6)	0.0213 (5)	0.0036 (4)	0.0029 (4)	0.0051 (5)	
C5	0.0258 (6)	0.0164 (5)	0.0164 (5)	0.0044 (4)	−0.0003 (4)	0.0037 (4)	
C10	0.0310 (7)	0.0246 (6)	0.0188 (5)	0.0035 (5)	−0.0053 (5)	0.0042 (5)	
C4	0.0326 (6)	0.0216 (5)	0.0132 (5)	0.0078 (5)	0.0035 (4)	0.0039 (4)	

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Geometric parameters (Å, º)

Sn1—Cl3	2.4180 (3)	C2—C1	1.5029 (15)	
Sn1—Cl3i	2.4180 (3)	C3—C4	1.3758 (17)	
Sn1—Cl1	2.4370 (3)	C3—H3	0.9300	
Sn1—Cl1i	2.4370 (3)	C6—C7	1.4067 (17)	
Sn1—Cl2i	2.4406 (3)	C6—C5	1.4220 (15)	
Sn1—Cl2	2.4406 (3)	C9—C10	1.364 (2)	
O2—C1	1.2099 (14)	C9—C8	1.4155 (19)	
O1—C1	1.3026 (14)	C9—H9	0.9300	
O1—H1	0.8200	C8—C7	1.3715 (17)	
O3—H3A	0.8511	C8—H8	0.9300	
O3—H3B	0.8496	C7—H7	0.9300	
N1—C2	1.3282 (14)	C5—C4	1.4041 (18)	
N1—C6	1.3649 (14)	C5—C10	1.4171 (17)	
N1—H1A	0.832 (17)	C10—H10	0.9300	
C2—C3	1.3927 (15)	C4—H4	0.9300	
				
Cl3—Sn1—Cl3i	179.999 (12)	O1—C1—C2	112.24 (10)	
Cl3—Sn1—Cl1	89.336 (10)	C4—C3—C2	118.86 (11)	
Cl3i—Sn1—Cl1	90.665 (10)	C4—C3—H3	120.6	
Cl3—Sn1—Cl1i	90.663 (10)	C2—C3—H3	120.6	
Cl3i—Sn1—Cl1i	89.336 (10)	N1—C6—C7	120.61 (10)	
Cl1—Sn1—Cl1i	180.0	N1—C6—C5	117.83 (10)	
Cl3—Sn1—Cl2i	91.121 (10)	C7—C6—C5	121.56 (11)	
Cl3i—Sn1—Cl2i	88.879 (10)	C10—C9—C8	120.70 (12)	
Cl1—Sn1—Cl2i	90.704 (10)	C10—C9—H9	119.6	
Cl1i—Sn1—Cl2i	89.295 (10)	C8—C9—H9	119.6	
Cl3—Sn1—Cl2	88.879 (10)	C7—C8—C9	121.41 (12)	
Cl3i—Sn1—Cl2	91.121 (10)	C7—C8—H8	119.3	
Cl1—Sn1—Cl2	89.295 (10)	C9—C8—H8	119.3	
Cl1i—Sn1—Cl2	90.706 (10)	C8—C7—C6	118.11 (11)	
Cl2i—Sn1—Cl2	180.0	C8—C7—H7	120.9	
C1—O1—H1	109.5	C6—C7—H7	120.9	
H3A—O3—H3B	109.4	C4—C5—C10	123.20 (11)	
C2—N1—C6	123.38 (10)	C4—C5—C6	118.68 (11)	
C2—N1—H1A	118.5 (11)	C10—C5—C6	118.11 (11)	
C6—N1—H1A	118.2 (11)	C9—C10—C5	120.10 (12)	
N1—C2—C3	120.58 (10)	C9—C10—H10	120.0	
N1—C2—C1	115.14 (10)	C5—C10—H10	120.0	
C3—C2—C1	124.29 (10)	C3—C4—C5	120.63 (11)	
O2—C1—O1	126.71 (11)	C3—C4—H4	119.7	
O2—C1—C2	121.05 (10)	C5—C4—H4	119.7	
				
C6—N1—C2—C3	1.99 (16)	N1—C6—C7—C8	−178.90 (11)	
C6—N1—C2—C1	−177.71 (10)	C5—C6—C7—C8	0.58 (18)	
N1—C2—C1—O2	−11.11 (16)	N1—C6—C5—C4	−1.35 (16)	
C3—C2—C1—O2	169.20 (11)	C7—C6—C5—C4	179.15 (11)	
N1—C2—C1—O1	168.63 (10)	N1—C6—C5—C10	178.41 (10)	
C3—C2—C1—O1	−11.06 (16)	C7—C6—C5—C10	−1.09 (17)	
N1—C2—C3—C4	−1.40 (17)	C8—C9—C10—C5	0.5 (2)	
C1—C2—C3—C4	178.27 (11)	C4—C5—C10—C9	−179.70 (12)	
C2—N1—C6—C7	178.92 (11)	C6—C5—C10—C9	0.55 (18)	
C2—N1—C6—C5	−0.58 (16)	C2—C3—C4—C5	−0.54 (18)	
C10—C9—C8—C7	−1.0 (2)	C10—C5—C4—C3	−177.86 (12)	
C9—C8—C7—C6	0.47 (19)	C6—C5—C4—C3	1.89 (17)	

Symmetry code: (i) −x, −y, −z.

Bis(2-carboxyquinolinium) hexachloridostannate(IV) dihydrate Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A	
O1—H1···O3	0.82	1.75	2.5684 (14)	176	
N1—H1A···O2ii	0.832 (17)	2.028 (17)	2.8348 (13)	163.4 (15)	
O3—H3A···Cl1	0.85	2.46	3.2048 (11)	146	
O3—H3B···Cl2i	0.85	2.61	3.3708 (11)	150	
C3—H3···Cl1iii	0.93	2.97	3.6014 (12)	127	
C7—H7···O2ii	0.93	2.58	3.2850 (15)	133	
C7—H7···O3ii	0.93	2.51	3.3144 (16)	146	

Symmetry codes: (i) −x, −y, −z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z+1.

Figure 1 View of the mol­ecular entities in (I) with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. [Symmetry code: (i) −x, −y, −z].

Figure 2 O—H⋯O, N—H⋯O and O—H⋯Cl hydrogen-bonding inter­actions in the crystal structure of (I) indicated by dashed lines. Symmetry codes refer to Table 1 ▸.

Figure 3 (a) π–π stacking inter­actions and (b) Cl⋯π inter­actions in the crystal structure of (I).

Table 1 Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A	
O1—H1⋯O3	0.82	1.75	2.5684 (14)	176	
N1—H1A⋯O2i	0.832 (17)	2.028 (17)	2.8348 (13)	163.4 (15)	
O3—H3A⋯Cl1	0.85	2.46	3.2048 (11)	146	
O3—H3B⋯Cl2ii	0.85	2.61	3.3708 (11)	150	
Symmetry codes: (i) ; (ii) .

Table 2 Experimental details

Crystal data	
Chemical formula	(C10H8NO2)[SnCl6]·2H2O	
M r	715.77	
Crystal system, space group	Triclinic, P	
Temperature (K)	296	
a, b, c (Å)	8.3220 (4), 9.2704 (4), 9.4248 (4)	
α, β, γ (°)	108.101 (2), 99.515 (2), 99.749 (2)	
V (Å3)	662.46 (5)	
Z	1	
Radiation type	Mo Kα	
μ (mm−1)	1.61	
Crystal size (mm)	0.10 × 0.09 × 0.08	
 	
Data collection	
Diffractometer	Bruker APEXII CCD	
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 ▸)	
Tmin, Tmax	0.851, 0.879	
No. of measured, independent and observed [I > 2σ(I)] reflections	19467, 3262, 3199	
R int	0.015	
(sin θ/λ)max (Å−1)	0.667	
 	
Refinement	
R[F2 > 2σ(F2)], wR(F2), S	0.013, 0.033, 1.08	
No. of reflections	3262	
No. of parameters	168	
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	
Δρmax, Δρmin (e Å−3)	0.41, −0.25	
Computer programs: APEX2 and SAINT (Bruker, 2013 ▸), OLEX2.solve (Bourhis et al., 2015 ▸), SHELXL (Sheldrick, 2015 ▸), OLEX2 (Dolomanov et al., 2009 ▸) and publCIF (Westrip, 2010 ▸).
==== Refs
References

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Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75.
Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
Gelmboldt, V. O., Ganin, E. V. & Domasevitch, K. V. (2007). Acta Cryst. C63, o530–o534.
Ghallab, R., Boutebdja, M., Dénès, G. & Merazig, H. (2020). Acta Cryst. E76, 1279–1283.
Hajlaoui, S., Chaabane, I., Oueslati, A. & Guidara, K. (2013). Solid State Sci. 25, 134–142.
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Rademeyer, M. (2004). Acta Cryst. C60, m55–m56.
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Smith, G., Wermuth, U. D. & White, J. M. (2004). Acta Cryst. C60, o575–o581.
Smith, G., Wermuth, U. D. & White, J. M. (2008). Acta Cryst. C64, o180–o183.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
