research communications
A new organic–inorganic compound, ethylenediammonium hexachloridostannate(IV) p-anisaldehyde disolvate
aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, bDépartement de Physique Chimie, Faculté des Sciences et Technologies de l'Education et de la Formation, Université Cheikh Anta Diop, Boulevard Habib, Bourguiba, BP 5036 Fann-Dakar, Senegal, and cInstitute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany
*Correspondence e-mail: andiolene@gmail.com
The 2H10N2)[SnCl6]·2C8H8O2, contains one half of an ethylenediammonium cation, one half of an [SnCl6]2− anion and one p-anisaldehyde molecule. Both the organic cation and the quasi-regular octahedral inorganic anion are located about inversion centres. The organic cations and [SnCl6]2− anions lie in layers parallel to the ac plane with p-anisaldehyde molecules occupying the space between the layers. A network of classical N—H⋯Cl and N—H⋯O hydrogen bonds exists between the ethylenediammonium cations and the [SnCl6]2− anions and p-anisaldehyde molecules. These interactions, together with non-classical C—H⋯O interactions between the ethylenediammonium cations and the p-anisaldehyde molecules, serve to hold the structure together. The crystal studied was refined as a two-component twin.
of the title organic–inorganic hybrid complex [systematic name: ethane-1,2-diaminium hexachloridostannate(IV)–4-methoxybenzaldehyde (1/2)], (CKeywords: crystal structure; hexachloridostannate(IV) complex; ethylenediammonium; p-anisaldehyde; organic–inorganic hybrid complex.
CCDC reference: 2063269
1. Chemical context
The combination of organic and inorganic components to form organic–inorganic hybrid materials has attracted considerable attention owing to the generation of new properties that are absent in type either of building block (Boopathi et al., 2017; Newman et al., 1989; Chun & Jung, 2009; Bouchene et al., 2018). Hybrid functional materials, containing both inorganic and organic components, are considered to be potential platforms for applications in extremely diverse fields, such as optics, micro-electronics, magnetism, vibrational spectroscopy, transportation, health, energy, energy storage, diagnosis, housing and the environment (Masteri-Farahani et al., 2012; Kim et al., 2020; Manser et al., 2016; Rademeyer et al., 2007). Moreover, halogenostannate hybrid compounds containing protonated amine cations have recently received considerable attention because of their interesting physical and chemical properties, such as magnetism, and conductivity, which may lead to technological innovations (Aruta et al., 2005; Chouaib & Kamoun, 2015; Papavassiliou et al., 1999; Yin & Yo, 1998). The structures of these hybrid materials have been shown to contain contain isolated or connected chains or clusters of SnX6 octahedra separated by amine cations (Zhou & Liu, 2012; Shahzadi et al., 2008; Liu, 2012; Diop et al., 2020). In this category of materials, the organic moieties, which balance the negative charge on the inorganic units, may also act as structure-directing agents and greatly affect the structure and dimensionality of the supramolecular framework formed (Díaz et al., 2006; Hannon et al., 2002). In the present study, we report the synthesis and structural analysis of a new organic–inorganic hybrid complex, (C2H10N2)[SnCl6]·2C8H8O2.
2. Structural commentary
The 6]2−, both of which lie on centres of inversion, and one molecule of p-anisaldehyde (Fig. 1). The environment around the tin atom in the [SnCl6]2− dianion is an almost undistorted octahedron in which the Sn—Cl bond lengths lie in the range 2.4100 (12) to 2.4322 (11) Å and the cis Cl—Sn—Cl bond angles lie in the range 89.36 (4) to 90.20 (4) °. The Sn—Cl2 bond involved in hydrogen bonding is slightly longer, at 2.4322 (11) Å, than the other Sn—Cl bonds [Sn—Cl1 = 2.4100 (12)Å and Sn—Cl3 = 2.4220 (11) Å]. These results are comparable to those reported by other research groups (van Megen et al., 2013; Ali et al., 2008; Xue & Kong 2014).
comprises of one half of an ethylenediammonium cation, one half of a hexachlorostannate(IV) dianion, [SnCl3. Supramolecular features
The packed ac plane in which each [SnCl6]2− dianion is surrounded by four ethylenediammonium cations (Fig. 2). The p-anisaldehyde molecules are located in the otherwise empty space between the sheets (Fig. 3). The crystal packing of the complex is supported by N—H⋯Cl and N—H⋯O hydrogen-bonding interactions (Table 1). The NH3+ groups of the ethylenediammonium cation act as the hydrogen-bonding donors. The D⋯A distances involving the NH3+ group and either the p-anisaldehyde molecule or the [SnCl6]2− units range from 2.763 (6) Å for N1⋯O2iii to 3.404 (4) Å for N1⋯Cl3v. Non-classical interactions between the p-anisaldehyde molecules and the ethylenediammonium cations, C9—H9⋯O2vi at 2.62 Å, further serve to hold the structure together.
contains sheets lying parallel to the4. Database survey
Organic–inorganic hybrid compounds with structures most similar to that of the title compound include: (C6H22N4)[SnCl6]Cl2·2H2O and (C8H24N4)[SnCl6]Cl2·2H2O (Bouchene et al. 2018), (C5H5BrN2)[SnCl6] (Ali et al., 2008), (C5H7N2)2[SnCl6], and (C7H10N)2[SnCl6] (Rademeyer et al., 2007) and (C8H12N)3SnBr6·Br (Chouaib & Kamoun, 2015). These structures contain isolated or connected chains or clusters of SnX6 octahedra separated by the organic cations. A variety of intermolecular hydrogen bonds, N—H⋯O, N—H⋯Cl and O—H⋯O, together with C—H⋯π interactions, serve to consolidate the molecular structures.
5. Synthesis and crystallization
Chemicals [p-anisaldehyde, ethylenediamine and tin(II)] were purchased from Sigma-Aldrich and were used without any further purification. The solvent use for the synthesis was ethanol (96%).
Synthesis of N,N′-bis(4-methoxybenzylidene)ethylenediamine
The Schiff base N,N′-bis(4-methoxybenzylidene)ethylenediamine was prepared by condensing p-anisaldehyde (10 g; 0.0734 mol) with ethylenediamine (2.205 g; 0.0367 mol) in ethanol (30 ml) (Fig. 4). The resulting mixture was heated under reflux for 6 h, filtered and left to evaporate at ambient temperature. (The reaction between p-anisaldehyde and ethylenediamine gave the same product whatever the proportions of reactants used). After a few days of slow evaporation, 4.511 g of crystals were obtained, corresponding to a yield of 82%. The compound was characterized by FT–IR (cm−1: 1639.05 (C=N); 1603, 1505, 1461 and 1448 (C=C, aromatic); 1019 (C—O, ether).
Synthesis of the title compound
0.3 g (0.00168 mol) of N,N′-bis (4-methoxybenzylidene)ethylenediamine were dissolved in 30 ml of ethanol in a round-bottomed flask, followed by the addition of SnCl2 (0.638 g; 0.00168 mol) to form a yellow solution (Fig. 5). The mixture was refluxed for 7 h at 353 K, filtered to remove Sn(OEt)6 and Sn(OH)2 and the resulting solution was allowed to evaporate slowly. After a few days of evaporation, light-yellow block-shaped crystals suitable for single-crystal X-ray analysis were obtained in a yield of 31%. The presence of water molecules in the solvent (EtOH, 96%) causes hydrolysis of the Schiff base and oxidation of tin(II) to tin(IV). The hydrolysis reaction leads to the formation of two molecules of p-anisaldehyde and one ethylenediammonium cation.
The crystalline product was characterized by FT–IR (cm−1: 1659 (C=O); 3290 (N—H); 2801 (C—H, aldehyde); 1596, 1570 and 1556 (C=C, phenyl); 1259 (C—O, ether).
6. Refinement
Crystal data, data collection and structure . (C2H10N2)[SnCl6]·2C8H8O2 crystallizes in the P21/n with the monoclinic angle, β, close to 90°. The crystals formed as non-merohedral twins with about one quarter of reflections overlapping. The corresponds to rotation about c*. For the crystal investigated, the relative domain sizes amounted to 0.790 (4): 0.210 (4). The structure was solved by intrinsic phasing (Sheldrick, 2015a). The was identified from reflections with Iobs >> Icalc, and PLATON (Spek, 2020) was used to generate a suitable two-domain reflection file for twin (Sheldrick, 2015b). All non-hydrogen atoms were assigned anisotropic displacement parameters. H atoms attached to C were calculated in standard geometry and treated as riding [C—H = 0.95–0.99 Å; Uiso(H) = 1.2Uiso(C) or 1.5Uiso(C-methyl)]. H atoms attached to N were located as local maxima in a difference-Fourier map and refined with a distance restraint N—H = 0.9 Å and an isotropic displacement parameter Uiso(H) = 1.2Uiso(N).
details are summarized in Table 2
|
Supporting information
CCDC reference: 2063269
https://doi.org/10.1107/S205698902100579X/cq2042sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902100579X/cq2042Isup2.hkl
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).(C2H10N2)[SnCl6]·2C8H8O2 | F(000) = 664 |
Mr = 665.80 | Dx = 1.729 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9762 (12) Å | Cell parameters from 4273 reflections |
b = 22.806 (4) Å | θ = 2.7–27.3° |
c = 8.0394 (13) Å | µ = 1.65 mm−1 |
β = 90.948 (4)° | T = 100 K |
V = 1278.9 (4) Å3 | Block, light yellow |
Z = 2 | 0.17 × 0.17 × 0.13 mm |
Bruker D8 gonimeter with APEX CCD detector diffractometer | 3929 independent reflections |
Radiation source: Incoatec microsource | 3182 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.112 |
ω scans | θmax = 30.9°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −9→9 |
k = −32→32 | |
3929 measured reflections | l = −11→11 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.062 | w = 1/[σ2(Fo2) + (0.090P)2 + 3.P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.164 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 2.91 e Å−3 |
3929 reflections | Δρmin = −2.69 e Å−3 |
154 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0073 (13) |
Primary atom site location: dual |
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. |
Refinement. Refined as a two-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0054 (6) | 0.20471 (16) | 0.5640 (5) | 0.0297 (8) | |
O2 | 0.0223 (7) | 0.35799 (17) | −0.0922 (5) | 0.0346 (9) | |
C1 | 0.0073 (7) | 0.2253 (2) | 0.4064 (6) | 0.0216 (9) | |
C2 | 0.0110 (8) | 0.1905 (2) | 0.2647 (6) | 0.0271 (11) | |
H2 | 0.011776 | 0.148942 | 0.273751 | 0.032* | |
C3 | 0.0134 (8) | 0.2171 (2) | 0.1100 (6) | 0.0261 (10) | |
H3 | 0.014641 | 0.193476 | 0.012738 | 0.031* | |
C4 | 0.0141 (8) | 0.2776 (2) | 0.0945 (6) | 0.0224 (9) | |
C5 | 0.0197 (8) | 0.3047 (2) | −0.0684 (7) | 0.0289 (11) | |
H5 | 0.021414 | 0.279678 | −0.162937 | 0.035* | |
C6 | 0.0097 (8) | 0.3121 (2) | 0.2377 (6) | 0.0262 (10) | |
H6 | 0.008962 | 0.353603 | 0.227991 | 0.031* | |
C7 | 0.0063 (9) | 0.2865 (2) | 0.3939 (7) | 0.0281 (11) | |
H7 | 0.003288 | 0.310129 | 0.491121 | 0.034* | |
C8 | 0.0077 (9) | 0.1422 (2) | 0.5874 (7) | 0.0299 (11) | |
H8A | −0.104360 | 0.124858 | 0.531118 | 0.045* | |
H8B | 0.003967 | 0.133301 | 0.706506 | 0.045* | |
H8C | 0.124940 | 0.125913 | 0.540404 | 0.045* | |
Sn1 | 0.000000 | 0.000000 | 0.000000 | 0.01522 (16) | |
Cl1 | −0.23806 (17) | 0.07591 (5) | −0.03230 (15) | 0.0231 (3) | |
Cl2 | 0.02718 (18) | 0.02031 (5) | 0.29645 (13) | 0.0225 (3) | |
Cl3 | 0.25385 (17) | 0.06982 (5) | −0.05138 (14) | 0.0207 (3) | |
N1 | 0.5008 (6) | 0.02942 (18) | 0.2818 (5) | 0.0209 (8) | |
H1A | 0.533 (8) | 0.0662 (13) | 0.313 (8) | 0.025* | |
H1B | 0.544 (9) | 0.015 (3) | 0.183 (5) | 0.025* | |
H1C | 0.372 (4) | 0.029 (3) | 0.255 (8) | 0.025* | |
C9 | 0.5429 (9) | −0.0111 (2) | 0.4218 (6) | 0.0259 (11) | |
H9A | 0.683408 | −0.014942 | 0.437370 | 0.031* | |
H9B | 0.490162 | −0.050389 | 0.395586 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.049 (2) | 0.0189 (17) | 0.0210 (17) | 0.0022 (16) | −0.0011 (16) | 0.0025 (13) |
O2 | 0.052 (3) | 0.0207 (18) | 0.031 (2) | −0.0010 (17) | 0.0017 (18) | 0.0066 (15) |
C1 | 0.030 (2) | 0.016 (2) | 0.019 (2) | 0.0003 (18) | −0.0028 (18) | 0.0013 (16) |
C2 | 0.043 (3) | 0.014 (2) | 0.025 (2) | 0.001 (2) | −0.001 (2) | −0.0011 (17) |
C3 | 0.041 (3) | 0.015 (2) | 0.022 (2) | −0.001 (2) | 0.001 (2) | −0.0024 (16) |
C4 | 0.030 (2) | 0.017 (2) | 0.020 (2) | −0.0004 (18) | −0.0019 (18) | 0.0007 (16) |
C5 | 0.040 (3) | 0.022 (2) | 0.024 (2) | 0.000 (2) | −0.001 (2) | 0.0026 (19) |
C6 | 0.042 (3) | 0.014 (2) | 0.023 (2) | 0.000 (2) | −0.001 (2) | −0.0024 (17) |
C7 | 0.044 (3) | 0.016 (2) | 0.024 (2) | 0.000 (2) | 0.000 (2) | −0.0026 (17) |
C8 | 0.043 (3) | 0.018 (2) | 0.029 (3) | 0.003 (2) | −0.002 (2) | 0.0067 (18) |
Sn1 | 0.0197 (3) | 0.0131 (2) | 0.0128 (2) | −0.00059 (15) | −0.00159 (15) | 0.00193 (13) |
Cl1 | 0.0246 (6) | 0.0173 (5) | 0.0275 (6) | 0.0032 (4) | 0.0004 (4) | 0.0059 (4) |
Cl2 | 0.0294 (6) | 0.0242 (6) | 0.0138 (5) | −0.0038 (5) | −0.0010 (4) | −0.0003 (4) |
Cl3 | 0.0240 (6) | 0.0181 (5) | 0.0199 (5) | −0.0040 (4) | −0.0016 (4) | 0.0032 (4) |
N1 | 0.028 (2) | 0.0205 (19) | 0.0145 (17) | −0.0016 (16) | −0.0025 (15) | 0.0007 (14) |
C9 | 0.035 (3) | 0.026 (2) | 0.017 (2) | 0.007 (2) | 0.003 (2) | 0.0041 (18) |
O1—C1 | 1.351 (6) | C8—H8B | 0.9800 |
O1—C8 | 1.438 (6) | C8—H8C | 0.9800 |
O2—C5 | 1.231 (6) | Sn1—Cl1i | 2.4100 (12) |
C1—C2 | 1.390 (7) | Sn1—Cl1 | 2.4100 (12) |
C1—C7 | 1.399 (7) | Sn1—Cl3i | 2.4220 (11) |
C2—C3 | 1.384 (7) | Sn1—Cl3 | 2.4220 (11) |
C2—H2 | 0.9500 | Sn1—Cl2i | 2.4322 (11) |
C3—C4 | 1.385 (6) | Sn1—Cl2 | 2.4322 (11) |
C3—H3 | 0.9500 | N1—C9 | 1.482 (6) |
C4—C6 | 1.395 (7) | N1—H1A | 0.902 (19) |
C4—C5 | 1.449 (7) | N1—H1B | 0.92 (2) |
C5—H5 | 0.9500 | N1—H1C | 0.925 (19) |
C6—C7 | 1.386 (7) | C9—C9ii | 1.490 (10) |
C6—H6 | 0.9500 | C9—H9A | 0.9900 |
C7—H7 | 0.9500 | C9—H9B | 0.9900 |
C8—H8A | 0.9800 | ||
C1—O1—C8 | 117.8 (4) | Cl1i—Sn1—Cl1 | 180.0 |
O1—C1—C2 | 124.8 (4) | Cl1i—Sn1—Cl3i | 90.80 (4) |
O1—C1—C7 | 114.4 (4) | Cl1—Sn1—Cl3i | 89.21 (4) |
C2—C1—C7 | 120.7 (5) | Cl1i—Sn1—Cl3 | 89.20 (4) |
C3—C2—C1 | 119.1 (4) | Cl1—Sn1—Cl3 | 90.79 (4) |
C3—C2—H2 | 120.4 | Cl3i—Sn1—Cl3 | 180.0 |
C1—C2—H2 | 120.4 | Cl1i—Sn1—Cl2i | 90.64 (4) |
C2—C3—C4 | 121.2 (5) | Cl1—Sn1—Cl2i | 89.36 (4) |
C2—C3—H3 | 119.4 | Cl3i—Sn1—Cl2i | 89.80 (4) |
C4—C3—H3 | 119.4 | Cl3—Sn1—Cl2i | 90.20 (4) |
C3—C4—C6 | 119.1 (5) | Cl1i—Sn1—Cl2 | 89.36 (4) |
C3—C4—C5 | 120.4 (5) | Cl1—Sn1—Cl2 | 90.64 (4) |
C6—C4—C5 | 120.5 (5) | Cl3i—Sn1—Cl2 | 90.20 (4) |
O2—C5—C4 | 124.2 (5) | Cl3—Sn1—Cl2 | 89.80 (4) |
O2—C5—H5 | 117.9 | Cl2i—Sn1—Cl2 | 180.0 |
C4—C5—H5 | 117.9 | C9—N1—H1A | 109 (4) |
C7—C6—C4 | 120.8 (4) | C9—N1—H1B | 111 (4) |
C7—C6—H6 | 119.6 | H1A—N1—H1B | 120 (6) |
C4—C6—H6 | 119.6 | C9—N1—H1C | 110 (4) |
C6—C7—C1 | 119.0 (5) | H1A—N1—H1C | 109 (6) |
C6—C7—H7 | 120.5 | H1B—N1—H1C | 97 (6) |
C1—C7—H7 | 120.5 | N1—C9—C9ii | 110.6 (5) |
O1—C8—H8A | 109.5 | N1—C9—H9A | 109.5 |
O1—C8—H8B | 109.5 | C9ii—C9—H9A | 109.5 |
H8A—C8—H8B | 109.5 | N1—C9—H9B | 109.5 |
O1—C8—H8C | 109.5 | C9ii—C9—H9B | 109.5 |
H8A—C8—H8C | 109.5 | H9A—C9—H9B | 108.1 |
H8B—C8—H8C | 109.5 | ||
C8—O1—C1—C2 | 0.1 (8) | C3—C4—C5—O2 | −179.3 (6) |
C8—O1—C1—C7 | −179.6 (5) | C6—C4—C5—O2 | 0.6 (9) |
O1—C1—C2—C3 | −179.7 (5) | C3—C4—C6—C7 | 0.6 (9) |
C7—C1—C2—C3 | −0.1 (9) | C5—C4—C6—C7 | −179.4 (5) |
C1—C2—C3—C4 | 0.6 (9) | C4—C6—C7—C1 | 0.0 (9) |
C2—C3—C4—C6 | −0.9 (9) | O1—C1—C7—C6 | 179.5 (5) |
C2—C3—C4—C5 | 179.1 (5) | C2—C1—C7—C6 | −0.2 (9) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cl1iii | 0.95 | 3.05 | 3.596 (5) | 118 |
N1—H1A···O2iii | 0.90 (2) | 1.89 (3) | 2.763 (6) | 162 (6) |
N1—H1B···Cl1iv | 0.92 (2) | 2.71 (5) | 3.312 (4) | 124 (5) |
N1—H1B···Cl3v | 0.92 (2) | 2.62 (4) | 3.404 (4) | 144 (5) |
N1—H1C···Cl2 | 0.92 (2) | 2.44 (3) | 3.315 (5) | 158 (6) |
N1—H1C···Cl3 | 0.92 (2) | 2.75 (6) | 3.292 (4) | 119 (5) |
C9—H9B···O2vi | 0.99 | 2.62 | 3.319 (7) | 128 |
Symmetry codes: (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1, y, z; (v) −x+1, −y, −z; (vi) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
The authors acknowledge the Cheikh Anta Diop University of Dakar (Sénégal) for support. The diffraction data were collected at RWTH Aachen University.
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