1,3-Benzothia­zolium tetra­chlorido­aurate(III) tetra­hydro­furan solvate

Hagos, T.K.; Nogai, S.D.; Dobrzańska, L.; Cronje, S.; Raubenheimer, H.G.

doi:10.1107/S1600536809003572

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages m255-m256

doi:10.1107/S1600536809003572

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1,3-Benzothiazolium tetrachloridoaurate(III) tetrahydrofuran solvate

Tesfamariam K. Hagos,^a Stefan D. Nogai,^a Liliana Dobrzańska,^a ^* Stephanie Cronje ^a and Helgard G. Raubenheimer ^a

^aDepartment of Chemistry, University of Stellenbosch, Private Bag X1, Matieland, South Africa
^*Correspondence e-mail: lianger@sun.ac.za

(Received 26 January 2009; accepted 29 January 2009; online 6 February 2009)

In the crystal structure of the title ionic compound (C₇H₆NS)[AuCl₄]·C₄H₈O, the [AuCl₄]⁻ anion shows a typical square-planar geometry. Numerous weak C—H⋯Cl hydrogen bonds between [AuCl₄]⁻ and the 1,3-benzothiazolium units form layers comprised of 24-membered rings in which hydrogen-bonded tetrahydrofuran (THF) solvent molecules are accommodated. C—H⋯Cl interactions between THF and [AuCl₄]⁻ from adjacent layers result in bilayers. These are further stabilized by π–π interactions between the thiazole and benzene rings [centroid–centroid distance = 3.971 (3) Å], resulting in the formation of a three-dimensional supramolecular assembly.

Related literature

For background, see: Hagos et al. (2008 ). For related compounds, see: Huynh et al. (2006 ); Yen et al. (2006 , 2008 ). For bond-length data, see Adé et al. (2004 ); Asaji et al. (2004 ); Makotchenko et al. (2006 ). For related literature, see: Brammer et al. (2001 ).

Experimental

Crystal data

(C₇H₆NS)[AuCl₄]·C₄H₈O
M_r = 547.06
Triclinic, $[P \overline 1]$
a = 7.3213 (7) Å
b = 10.3498 (10) Å
c = 11.8783 (12) Å
α = 99.331 (1)°
β = 107.579 (1)°
γ = 104.483 (2)°
V = 802.75 (14) Å³
Z = 2
Mo Kα radiation
μ = 9.95 mm⁻¹
T = 100 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.101, T_max = 0.371
4957 measured reflections
3504 independent reflections
3325 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.064
S = 1.05
3504 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.27 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O14	0.86 (5)	1.87 (5)	2.728 (5)	177 (6)
C5—H5⋯Cl2ⁱ	0.95	2.65	3.588 (5)	170
C8—H8⋯Cl4	0.95	2.93	3.447 (5)	116
C9—H9⋯Cl4	0.95	3.00	3.498 (5)	114
C10—H10⋯Cl2ⁱⁱ	0.95	2.96	3.541 (6)	121
C11—H11⋯Cl2ⁱⁱ	0.95	2.90	3.498 (5)	122
C11—H11⋯Cl3ⁱⁱ	0.95	2.77	3.639 (5)	154
C15—H15B⋯Cl1ⁱⁱⁱ	0.99	3.02	3.922 (6)	153
C18—H18A⋯Cl4ⁱⁱⁱ	0.99	2.91	3.547 (6)	123
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003572/ng2541sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003572/ng2541Isup2.hkl

checkCIF report

Comment top

During the course of ongoing studies on the reactions of gold(III) compounds with heterocycles, we have isolated the title ionic compound (I) with a structure resembling that of a 1,3-dimesitylimidazolinium tetrachloro-gold(III) dichloromethane solvate reported earlier (Hagos et al. 2008). The asymmetric unit (Fig. 1) consists of a 1,3-benzothiazolium cation, a tetrachloro-gold(III) anion and a tetrahydrofuran molecule. The structural parameters associated with the 1,3-benzothiazolium moiety agree well with reported values, see for example 3-(2-propenyl)-1,3-benzothiazolium bromide (Huynh et al. 2006), N-benzyl-1,3-benzothiazolium bromide (Yen et al. 2006) and 3-n-propyl-1,3-benzothiazolium bromide monohydrate (Yen et al. 2008). The anionic part displays a typical square-planar geometry around Au and the Au—Cl distances compare well with previously reported values (Adé et al., 2004; Asaji et al., 2004; Makotchenko et al., 2006). All Cl atoms of [AuCl₄]^- complex participate in the formation of weak C—H···Cl hydrogen bonds (Table 1). Atoms Cl2, Cl3 and Cl4 interact with the 1,3-benzothiazolium cation forming layers consisting of R⁵₆(24) rings in which tetrahydrofuran molecules are incorporated by forming hydrogen bonds O6—H6···N14 with a distance of 2.728 (5) Å (Fig. 2). Further C—H···Cl interactions between THF and [AuCl₄]^- from neighbouring layers (C15—H15B···Cl1 and C18—H18A···Cl4) form pillar-like connections between them, leading to the formation of bilayers. The latter are propagated along [100] by π-π interactions between thiazole and benzene rings [symmetry operation: 1 - x, 1 - y, 2 - z, centroid-centroid distance = 3.971 (3) Å], resulting in a three-dimensional assembly (Fig. 3).

Related literature top

For background, see: Hagos et al. (2008). For related compounds, see: Huynh et al. (2006); Yen et al. (2006, 2008). For bond-length data, see Adé et al. (2004); Asaji et al. (2004); Makotchenko et al. (2006). For related literature, see: Brammer et al. (2001).

Experimental top

1,3-Benzothiazole (0.10 g, 0.76 mmol) in acetonitrile (5 ml) was treated with HAuCl₄^.4H₂O (0.31 g, 0.76 mmol) in water (5 ml) at room temperature (2.5 h). The reaction mixture was stripped of solvent and extracted with a mixture of dichloromethane and THF (1:1, 150 ml). Then the solvent was removed under reduced pressure to yield a yellow residue. Orange crystals suitable for single-crystal X-ray analysis were obtained from a THF solution layered with n-pentane at 253 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Capped-stick representation showing the formation of layers consisting of R⁵₆(24) rings (shown in black). Dashed orange lines represent C—H···Cl hydrogen bonds.
	Fig. 3. Representation of the bilayers (red-green) with pillar-like connections (yellow dashed lines) extended in the third dimension by π-π interactions (blue dashed lines) viewed down [010].

1,3-Benzothiazolium tetrachloridoaurate(III) tetrahydrofuran solvate top

Crystal data top

(C₇H₆NS)[AuCl₄]·C₄H₈O	Z = 2
M_r = 547.06	F(000) = 516
Triclinic, P1	D_x = 2.263 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3213 (7) Å	Cell parameters from 3347 reflections
b = 10.3498 (10) Å	θ = 2.4–28.1°
c = 11.8783 (12) Å	µ = 9.95 mm⁻¹
α = 99.331 (1)°	T = 100 K
β = 107.579 (1)°	Block, orange
γ = 104.483 (2)°	0.30 × 0.20 × 0.10 mm
V = 802.75 (14) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	3504 independent reflections
Radiation source: fine-focus sealed tube	3325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
T_min = 0.101, T_max = 0.371	k = −13→13
4957 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0432P)² + 0.5801P] where P = (F_o² + 2F_c²)/3
3504 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 2.27 e Å⁻³
1 restraint	Δρ_min = −1.00 e Å⁻³

Crystal data top

(C₇H₆NS)[AuCl₄]·C₄H₈O	γ = 104.483 (2)°
M_r = 547.06	V = 802.75 (14) Å³
Triclinic, P1	Z = 2
a = 7.3213 (7) Å	Mo Kα radiation
b = 10.3498 (10) Å	µ = 9.95 mm⁻¹
c = 11.8783 (12) Å	T = 100 K
α = 99.331 (1)°	0.30 × 0.20 × 0.10 mm
β = 107.579 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3504 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3325 reflections with I > 2σ(I)
T_min = 0.101, T_max = 0.371	R_int = 0.013
4957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 2.27 e Å⁻³
3504 reflections	Δρ_min = −1.00 e Å⁻³
175 parameters

Special details top

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
Au1	0.00874 (2)	0.215338 (16)	0.234396 (14)	0.01707 (7)
Cl1	0.03040 (19)	−0.00191 (12)	0.22763 (11)	0.0318 (3)
Cl2	−0.26390 (17)	0.12764 (11)	0.05577 (10)	0.0235 (2)
Cl3	−0.00788 (18)	0.43396 (11)	0.24088 (10)	0.0249 (2)
Cl4	0.27948 (17)	0.29983 (13)	0.41246 (10)	0.0287 (2)
C5	0.6777 (7)	0.7714 (5)	0.9404 (4)	0.0215 (9)
H5	0.6992	0.8678	0.9629	0.026*
N6	0.5448 (6)	0.6896 (4)	0.8362 (3)	0.0207 (8)
H6	0.477 (7)	0.718 (5)	0.778 (4)	0.025*
C7	0.5351 (7)	0.5514 (4)	0.8204 (4)	0.0178 (8)
C8	0.4115 (7)	0.4415 (5)	0.7204 (4)	0.0233 (9)
H8	0.3166	0.4541	0.6517	0.028*
C9	0.4313 (8)	0.3142 (5)	0.7244 (4)	0.0276 (10)
H9	0.3487	0.2370	0.6571	0.033*
C10	0.5711 (8)	0.2954 (5)	0.8257 (5)	0.0276 (10)
H10	0.5811	0.2056	0.8254	0.033*
C11	0.6940 (7)	0.4035 (5)	0.9253 (4)	0.0231 (9)
H11	0.7888	0.3903	0.9936	0.028*
C12	0.6738 (6)	0.5330 (4)	0.9220 (4)	0.0182 (8)
S13	0.80728 (17)	0.68998 (12)	1.03100 (10)	0.0219 (2)
O14	0.3180 (5)	0.7755 (3)	0.6536 (3)	0.0219 (7)
C15	0.3808 (7)	0.9178 (5)	0.6497 (4)	0.0227 (9)
H15B	0.5216	0.9468	0.6520	0.027*
H15A	0.3715	0.9791	0.7195	0.027*
C16	0.2358 (8)	0.9226 (5)	0.5300 (5)	0.0286 (10)
H16B	0.2955	1.0014	0.5009	0.034*
H16A	0.1068	0.9286	0.5372	0.034*
C17	0.2060 (9)	0.7850 (5)	0.4458 (5)	0.0335 (12)
H17A	0.0746	0.7534	0.3772	0.040*
H17B	0.3159	0.7918	0.4127	0.040*
C18	0.2116 (7)	0.6889 (5)	0.5298 (4)	0.0241 (9)
H18B	0.0726	0.6352	0.5198	0.029*
H18A	0.2830	0.6236	0.5108	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.01437 (9)	0.01940 (10)	0.01510 (9)	0.00527 (6)	0.00270 (6)	0.00332 (6)
Cl1	0.0340 (7)	0.0253 (6)	0.0289 (6)	0.0156 (5)	−0.0022 (5)	0.0042 (5)
Cl2	0.0220 (5)	0.0200 (5)	0.0205 (5)	0.0076 (4)	−0.0028 (4)	0.0022 (4)
Cl3	0.0284 (6)	0.0196 (5)	0.0221 (5)	0.0062 (4)	0.0045 (4)	0.0038 (4)
Cl4	0.0211 (5)	0.0370 (6)	0.0194 (5)	0.0097 (5)	−0.0013 (4)	0.0004 (5)
C5	0.025 (2)	0.019 (2)	0.023 (2)	0.0104 (18)	0.0086 (19)	0.0063 (18)
N6	0.0214 (19)	0.0210 (19)	0.0190 (18)	0.0094 (16)	0.0037 (15)	0.0059 (15)
C7	0.017 (2)	0.020 (2)	0.016 (2)	0.0064 (17)	0.0048 (17)	0.0062 (17)
C8	0.024 (2)	0.025 (2)	0.015 (2)	0.0063 (19)	0.0024 (18)	0.0030 (18)
C9	0.034 (3)	0.020 (2)	0.020 (2)	0.007 (2)	0.002 (2)	−0.0006 (18)
C10	0.034 (3)	0.021 (2)	0.026 (2)	0.013 (2)	0.005 (2)	0.0068 (19)
C11	0.025 (2)	0.021 (2)	0.022 (2)	0.0102 (19)	0.0023 (18)	0.0085 (18)
C12	0.014 (2)	0.020 (2)	0.017 (2)	0.0045 (17)	0.0016 (16)	0.0039 (17)
S13	0.0206 (5)	0.0221 (5)	0.0177 (5)	0.0071 (4)	0.0009 (4)	0.0025 (4)
O14	0.0250 (17)	0.0173 (15)	0.0198 (16)	0.0060 (13)	0.0031 (13)	0.0058 (12)
C15	0.025 (2)	0.020 (2)	0.024 (2)	0.0075 (19)	0.0089 (19)	0.0080 (18)
C16	0.035 (3)	0.025 (2)	0.028 (3)	0.013 (2)	0.009 (2)	0.010 (2)
C17	0.041 (3)	0.027 (3)	0.025 (3)	0.007 (2)	0.005 (2)	0.007 (2)
C18	0.023 (2)	0.025 (2)	0.020 (2)	0.0081 (19)	0.0012 (18)	0.0032 (18)

Geometric parameters (Å, º) top

Au1—Cl4	2.2733 (11)	C11—C12	1.390 (6)
Au1—Cl1	2.2835 (12)	C11—H11	0.9500
Au1—Cl2	2.2850 (11)	C12—S13	1.741 (4)
Au1—Cl3	2.2864 (11)	O14—C15	1.443 (5)
C5—N6	1.310 (6)	O14—C18	1.450 (5)
C5—S13	1.686 (4)	C15—C16	1.513 (6)
C5—H5	0.9500	C15—H15B	0.9900
N6—C7	1.392 (6)	C15—H15A	0.9900
N6—H6	0.86 (5)	C16—C17	1.525 (7)
C7—C8	1.387 (6)	C16—H16B	0.9900
C7—C12	1.398 (6)	C16—H16A	0.9900
C8—C9	1.368 (7)	C17—C18	1.518 (7)
C8—H8	0.9500	C17—H17A	0.9900
C9—C10	1.402 (7)	C17—H17B	0.9900
C9—H9	0.9500	C18—H18B	0.9900
C10—C11	1.373 (7)	C18—H18A	0.9900
C10—H10	0.9500

Cl4—Au1—Cl1	90.14 (4)	C11—C12—S13	128.7 (3)
Cl4—Au1—Cl2	179.27 (4)	C7—C12—S13	110.4 (3)
Cl1—Au1—Cl2	89.16 (4)	C5—S13—C12	90.5 (2)
Cl4—Au1—Cl3	89.45 (4)	C15—O14—C18	109.0 (3)
Cl1—Au1—Cl3	179.07 (4)	O14—C15—C16	104.8 (4)
Cl2—Au1—Cl3	91.25 (4)	O14—C15—H15B	110.8
N6—C5—S13	114.0 (3)	C16—C15—H15B	110.8
N6—C5—H5	123.0	O14—C15—H15A	110.8
S13—C5—H5	123.0	C16—C15—H15A	110.8
C5—N6—C7	114.4 (4)	H15B—C15—H15A	108.9
C5—N6—H6	124 (4)	C15—C16—C17	101.8 (4)
C7—N6—H6	121 (4)	C15—C16—H16B	111.4
C8—C7—N6	127.8 (4)	C17—C16—H16B	111.4
C8—C7—C12	121.4 (4)	C15—C16—H16A	111.4
N6—C7—C12	110.8 (4)	C17—C16—H16A	111.4
C9—C8—C7	117.5 (4)	H16B—C16—H16A	109.3
C9—C8—H8	121.3	C18—C17—C16	102.9 (4)
C7—C8—H8	121.3	C18—C17—H17A	111.2
C8—C9—C10	121.4 (5)	C16—C17—H17A	111.2
C8—C9—H9	119.3	C18—C17—H17B	111.2
C10—C9—H9	119.3	C16—C17—H17B	111.2
C11—C10—C9	121.7 (4)	H17A—C17—H17B	109.1
C11—C10—H10	119.2	O14—C18—C17	106.7 (4)
C9—C10—H10	119.2	O14—C18—H18B	110.4
C10—C11—C12	117.2 (4)	C17—C18—H18B	110.4
C10—C11—H11	121.4	O14—C18—H18A	110.4
C12—C11—H11	121.4	C17—C18—H18A	110.4
C11—C12—C7	120.9 (4)	H18B—C18—H18A	108.6

S13—C5—N6—C7	0.3 (5)	N6—C7—C12—C11	−178.5 (4)
C5—N6—C7—C8	−179.6 (5)	C8—C7—C12—S13	179.4 (4)
C5—N6—C7—C12	−0.3 (5)	N6—C7—C12—S13	0.1 (5)
N6—C7—C8—C9	178.7 (5)	N6—C5—S13—C12	−0.2 (4)
C12—C7—C8—C9	−0.5 (7)	C11—C12—S13—C5	178.6 (4)
C7—C8—C9—C10	0.0 (8)	C7—C12—S13—C5	0.0 (4)
C8—C9—C10—C11	0.1 (9)	C18—O14—C15—C16	24.2 (5)
C9—C10—C11—C12	0.2 (8)	O14—C15—C16—C17	−37.1 (5)
C10—C11—C12—C7	−0.6 (7)	C15—C16—C17—C18	35.6 (5)
C10—C11—C12—S13	−179.0 (4)	C15—O14—C18—C17	−1.1 (5)
C8—C7—C12—C11	0.8 (7)	C16—C17—C18—O14	−22.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O14	0.86 (5)	1.87 (5)	2.728 (5)	177 (6)
C5—H5···Cl2ⁱ	0.95	2.65	3.588 (5)	170
C8—H8···Cl4	0.95	2.93	3.447 (5)	116
C9—H9···Cl4	0.95	3.00	3.498 (5)	114
C10—H10···Cl2ⁱⁱ	0.95	2.96	3.541 (6)	121
C11—H11···Cl2ⁱⁱ	0.95	2.90	3.498 (5)	122
C11—H11···Cl3ⁱⁱ	0.95	2.77	3.639 (5)	154
C15—H15B···Cl1ⁱⁱⁱ	0.99	3.02	3.922 (6)	153
C18—H18A···Cl4ⁱⁱⁱ	0.99	2.91	3.547 (6)	123

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

Experimental details

Crystal data
Chemical formula	(C₇H₆NS)[AuCl₄]·C₄H₈O
M_r	547.06
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3213 (7), 10.3498 (10), 11.8783 (12)
α, β, γ (°)	99.331 (1), 107.579 (1), 104.483 (2)
V (Å³)	802.75 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	9.95
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.101, 0.371
No. of measured, independent and observed [I > 2σ(I)] reflections	4957, 3504, 3325
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.064, 1.05
No. of reflections	3504
No. of parameters	175
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.27, −1.00

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O14	0.86 (5)	1.87 (5)	2.728 (5)	177 (6)
C5—H5···Cl2ⁱ	0.95	2.65	3.588 (5)	170
C8—H8···Cl4	0.95	2.93	3.447 (5)	116
C9—H9···Cl4	0.95	3.00	3.498 (5)	114
C10—H10···Cl2ⁱⁱ	0.95	2.96	3.541 (6)	121
C11—H11···Cl2ⁱⁱ	0.95	2.90	3.498 (5)	122
C11—H11···Cl3ⁱⁱ	0.95	2.77	3.639 (5)	154
C15—H15B···Cl1ⁱⁱⁱ	0.99	3.02	3.922 (6)	153
C18—H18A···Cl4ⁱⁱⁱ	0.99	2.91	3.547 (6)	123

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

Acknowledgements

The authors thank the National Research Foundation of South Africa and the University of Stellenbosch for financial support.

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