A new organic–inorganic compound, ethyl­enedi­ammonium hexa­chlorido­stannate(IV) p-anisaldehyde disolvate

Ndiolene, A.; Diop, T.; Boye, M.S.; Diasse-Sarr, A.; Englert, U.

doi:10.1107/S205698902100579X

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ISSN: 2056-9890

Volume 77| Part 7| July 2021| Pages 696-699

https://doi.org/10.1107/S205698902100579X

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A new organic–inorganic compound, ethylenediammonium hexachloridostannate(IV) p-anisaldehyde disolvate

Adrienne Ndiolene,^a ^* Tidiane Diop,^a Mouhamadou Sembène Boye,^b Aminata Diasse-Sarr ^a and Ulli Englert ^c

^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

Edited by A. M. Chippindale, University of Reading, England (Received 31 March 2021; accepted 3 June 2021; online 8 June 2021)

The asymmetric unit of the title organic–inorganic hybrid complex [systematic name: ethane-1,2-diaminium hexachloridostannate(IV)–4-methoxybenzaldehyde (1/2)], (C₂H₁₀N₂)[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.

Keywords: 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, electroluminescence, photoluminescence 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 asymmetric unit comprises of one half of an ethylenediammonium cation, one half of a hexachlorostannate(IV) dianion, [SnCl₆]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 ).

Figure 1
The atom-numbering for the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) −x, −y, −z; (ii) −x + 1, −y, −z + 1.]

3. Supramolecular features

The packed crystal structure contains sheets lying parallel to the 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⋯Cl3^v. Non-classical interactions between the p-anisaldehyde molecules and the ethylenediammonium cations, C9—H9⋯O2^vi at 2.62 Å, further serve to hold the structure together.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cl1ⁱ	0.95	3.05	3.596 (5)	118
N1—H1A⋯O2ⁱ	0.90 (2)	1.89 (3)	2.763 (6)	162 (6)
N1—H1B⋯Cl1ⁱⁱ	0.92 (2)	2.71 (5)	3.312 (4)	124 (5)
N1—H1B⋯Cl3ⁱⁱⁱ	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⋯O2^iv	0.99	2.62	3.319 (7)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
The arrangement of the (C₂H₁₀N₂)²⁻ and [SnCl₆]²⁻ units of the title compound in the ac plane showing the N1—H1C⋯Cl2 and N1—H1A⋯O2 hydrogen bonds as dashed lines.

Figure 3
View of the title compound along the c axis showing the organic cation–inorganic anion layers separated by p-anisaldehyde molecules. Hydrogen bonds are indicated by dashed lines.

4. 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).

Figure 4
Synthesis of the intermediate N,N′-bis(4-methoxybenzylidene)ethylenediamine.

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.

Figure 5
Synthesis of the title compound.

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 refinement details are summarized in Table 2. (C₂H₁₀N₂)[SnCl₆]·2C₈H₈O₂ crystallizes in the space group 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 twin law 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 twin law was identified from reflections with I_obs >> I_calc, and PLATON (Spek, 2020 ) was used to generate a suitable two-domain reflection file for twin refinement (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; U_iso(H) = 1.2U_iso(C) or 1.5U_iso(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 U_iso(H) = 1.2U_iso(N).

Table 2
Experimental details

Crystal data
Chemical formula	(C₂H₁₀N₂)[SnCl₆]·2C₈H₈O₂
M_r	665.80
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.9762 (12), 22.806 (4), 8.0394 (13)
β (°)	90.948 (4)
V (Å³)	1278.9 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.65
Crystal size (mm)	0.17 × 0.17 × 0.13

Data collection
Diffractometer	Bruker D8 gonimeter with APEX CCD detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
No. of measured, independent and observed [I > 2σ(I)] reflections	3929, 3929, 3182
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.723

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.164, 1.07
No. of reflections	3929
No. of parameters	154
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.91, −2.69
Computer programs: SMART (Bruker, 2002 ), SAINT (Bruker, 2009 ), SHELXT (Sheldrick 2015a), SHELXL2018/3 (Sheldrick, 2015b) and PLATON (Spek, 2020).

Supporting information

CCDC reference: 2063269

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902100579X/cq2042sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902100579X/cq2042Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

Ethane-1,2-diaminium hexachloridostannate(IV)–4-methoxybenzaldehyde (1/2) top

Crystal data top

(C₂H₁₀N₂)[SnCl₆]·2C₈H₈O₂	F(000) = 664
M_r = 665.80	D_x = 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

Data collection top

Bruker D8 gonimeter with APEX CCD detector diffractometer	3929 independent reflections
Radiation source: Incoatec microsource	3182 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.112
ω scans	θ_max = 30.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
	k = −32→32
3929 measured reflections	l = −11→11

Refinement top

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(F_o²) + (0.090P)² + 3.P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.164	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 2.91 e Å⁻³
3929 reflections	Δρ_min = −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

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.92 (2)	2.71 (5)	3.312 (4)	124 (5)
N1—H1B···Cl3^v	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···O2^vi	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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