Poly[μ-aqua-μ5-[2-(2,3,6-tri­chloro­phenyl)acetato]-caesium]

Smith, G.

doi:10.1107/S1600536813029395

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page m628

doi:10.1107/S1600536813029395

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Poly[μ-aqua-μ₅-[2-(2,3,6-trichlorophenyl)acetato]-caesium]

Graham Smith ^a ^*

^aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 22 October 2013; accepted 25 October 2013; online 6 November 2013)

In the structure of the title complex, [Cs(C₈H₄Cl₃O₂)(H₂O)]_n, the caesium salt of the commercial herbicide fenac [(2,3,6-trichlorophenyl)acetic acid], the irregular eight-coordination about Cs⁺ comprises a bidentate O:Cl-chelate interaction involving a carboxylate-O atom and an ortho-related ring-substituted Cl atom, which is also bridging, a triple-bridging carboxylate-O atom and a bridging water molecule. A two-dimensional polymer is generated, lying parallel to (100), within which there are water–carboxylate O—H⋯O hydrogen-bonding interactions.

CCDC reference: 968583

Related literature

For background information on the herbicide fenac, see: O'Neil (2001 ). For the structure of fenac, see: White et al. (1979 ). For examples of caesium complexes involving coordinating carbon-bound Cl, see: Levitskaia et al. (2000 ); Smith (2013 ).

Experimental

Crystal data

[Cs(C₈H₄Cl₃O₂)(H₂O)]
M_r = 389.39
Monoclinic, P 2₁ /c
a = 17.0606 (12) Å
b = 4.9834 (3) Å
c = 13.9283 (10) Å
β = 98.127 (6)°
V = 1172.29 (14) Å³
Z = 4
Mo Kα radiation
μ = 3.82 mm⁻¹
T = 200 K
0.20 × 0.15 × 0.07 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.582, T_max = 0.980
7585 measured reflections
2284 independent reflections
1873 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.111
S = 1.09
2284 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 2.18 e Å⁻³
Δρ_min = −1.86 e Å⁻³

Table 1
Selected bond lengths (Å)

Cs1—Cl6	3.711 (2)
Cs1—O1W	3.131 (6)
Cs1—O13	3.246 (7)
Cs1—Cl6ⁱ	3.646 (2)
Cs1—O1Wⁱ	3.148 (6)
Cs1—O12ⁱⁱ	3.213 (5)
Cs1—O12ⁱⁱⁱ	3.103 (6)
Cs1—O12^iv	3.242 (6)
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+2, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O13ⁱⁱ	0.97	1.70	2.638 (8)	161
O1W—H12W⋯O12^v	0.84	2.40	3.191 (8)	158
Symmetry codes: (ii) -x+2, -y+2, -z+1; (v) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ) within WinGX (Farrugia, 2012 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

CCDC reference: 968583

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813029395/wm2781sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029395/wm2781Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029395/wm2781Isup3.cml

checkCIF report

Comment top

(2,3,6-Trichlorophenyl)acetic acid (fenac) is a commercial herbicide (O'Neil, 2001) and its crystal structure (White et al., 1979) represents the only entry for this compound in the crystallographic literature. My interest in aromatic carboxylic acid herbicides and in polymeric coordination structures of the alkali metal complexes led to the preparation of the title compound, [Cs(C₈H₄Cl₃O₂)(H₂O)]_n, from the reaction of fenac with caesium hydroxide in aqueous ethanol, and the structure is reported herein.

In this structure (Fig. 1), the irregular eight-coordinate CsClO₇ polyhedron comprises a bidentate O:Cl-chelate interaction involving a carboxylate O-atom (O13) and an ortho-related ring substituted Cl-atom (Cl6) which is also bridging, a triple-bridging carboxylate O-atom (O12) and a bridging water molecule O1W (Table 1). A partial expansion of the asymmetric unit in the polymer structure is shown in Fig. 2, forming 4-, 7- and 8-membered cyclic associations linking Cs⁺ ions (a triple bridge involving Cl6, O1W and O12ⁱⁱⁱ, extending down b). The minimum Cs···Cs^vi bridging distance in the structure is 4.4336 (9) Å [for symmetry code (i), see Table 1. For code (vi): -x + 2, y + 1/2, -z + 3/2]. In the Cl bridge, the Cs—Cl bond lengths [3.646 (2) and 3.711 (2) Å] are long compared to those commonly present in the few known examples of caesium complexes having coordinating carbon-bound Cl atoms, e.g. 3.46–3.56 Å for a complex in which 1,2-dichloroethane acts as a bidentate chelate ligand (Levitskaia et al., 2000). However, I have previously reported values similar to those in the title complex in the analogous polymeric structure of caesium 4-amino-3,5,6-trichloropyridine-2-carboxylate monohydrate [3.6052 (11)– 3.7151 (11) Å], in which all three ring-substituted Cl-atoms are coordinated (Smith, 2013).

In the crystal structure of the title complex, a polymer with a sheet structure is generated which lies parallel to (100) (Fig. 3), and within which there are _waterO—H···O_carboxylate hydrogen-bonding interactions (Table 2).

Related literature top

For background information on the herbicide fenac, see: O'Neil (2001). For the structure of fenac, see: White et al. (1979). For examples of caesium complexes involving coordinating carbon-bound Cl, see: Levitskaia et al. (2000); Smith (2013).

Experimental top

The title compound was synthesized by heating together under reflux for 10 minutes, 0.5 mmol of (2,3,6-trichlorophenyl)acetic acid and 0.5 mmol of CsOH in 15 ml of 10% ethanol–water. Partial room temperature evaporation of the solution gave thin colourless crystal plates of the title complex from which a specimen was cleaved for the X-ray analysis.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids. [For symmetry codes, see Table 1.]
	Fig. 2. A partial expansion of the Cs⁺ coordination in the polymer generated by cyclic links through carboxylate, chlorine and water bridges. Ligand H-atoms are omitted. [For symmetry code (vi): -x + 2, y + 1/2, -z + 3/2. For other codes, see Fig. 1 and Table 1.]
	Fig. 3. The packing of the sheet structure in the unit cell viewed down b.

Poly[µ-aqua-µ₅-[2-(2,3,6-trichlorophenyl)acetato]-caesium] top

Crystal data top

[Cs(C₈H₄Cl₃O₂)(H₂O)]	F(000) = 736
M_r = 389.39	D_x = 2.206 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2248 reflections
a = 17.0606 (12) Å	θ = 3.3–28.0°
b = 4.9834 (3) Å	µ = 3.82 mm⁻¹
c = 13.9283 (10) Å	T = 200 K
β = 98.127 (6)°	Plate, colourless
V = 1172.29 (14) Å³	0.20 × 0.15 × 0.07 mm
Z = 4

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	2284 independent reflections
Radiation source: Enhance (Mo) X-ray source	1873 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.077 pixels mm^-1	θ_max = 26.0°, θ_min = 3.4°
ω scans	h = −20→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
T_min = 0.582, T_max = 0.980	l = −17→12
7585 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0285P)² + 9.056P] where P = (F_o² + 2F_c²)/3
2284 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 2.18 e Å⁻³
0 restraints	Δρ_min = −1.86 e Å⁻³

Crystal data top

[Cs(C₈H₄Cl₃O₂)(H₂O)]	V = 1172.29 (14) Å³
M_r = 389.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.0606 (12) Å	µ = 3.82 mm⁻¹
b = 4.9834 (3) Å	T = 200 K
c = 13.9283 (10) Å	0.20 × 0.15 × 0.07 mm
β = 98.127 (6)°

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	2284 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	1873 reflections with I > 2σ(I)
T_min = 0.582, T_max = 0.980	R_int = 0.034
7585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.09	Δρ_max = 2.18 e Å⁻³
2284 reflections	Δρ_min = −1.86 e Å⁻³
136 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cs1	0.91683 (3)	1.08611 (9)	0.65098 (4)	0.0524 (2)
Cl2	0.66412 (12)	1.1809 (4)	0.23490 (12)	0.0501 (6)
Cl3	0.53476 (12)	1.4225 (4)	0.34892 (17)	0.0616 (8)
Cl6	0.76993 (11)	0.5765 (4)	0.54801 (14)	0.0508 (6)
O1W	1.0140 (3)	0.5882 (12)	0.5977 (4)	0.065 (2)
O12	0.8947 (3)	0.8961 (12)	0.2855 (4)	0.0529 (19)
O13	0.8658 (3)	1.0892 (13)	0.4175 (5)	0.072 (2)
C1	0.7124 (3)	0.8850 (12)	0.3931 (4)	0.0274 (17)
C2	0.6586 (4)	1.0773 (13)	0.3521 (4)	0.0326 (19)
C3	0.6013 (4)	1.1852 (14)	0.4022 (5)	0.0367 (19)
C4	0.5961 (4)	1.1051 (15)	0.4948 (5)	0.040 (2)
C5	0.6479 (4)	0.9137 (15)	0.5385 (5)	0.039 (2)
C6	0.7052 (4)	0.8101 (13)	0.4877 (5)	0.0322 (19)
C11	0.7748 (4)	0.7685 (14)	0.3401 (5)	0.036 (2)
C12	0.8505 (4)	0.9352 (12)	0.3479 (4)	0.0307 (19)
H4	0.55790	1.17900	0.52840	0.0480*
H5	0.64430	0.85520	0.60120	0.0470*
H11A	0.75320	0.75000	0.27210	0.0430*
H11B	0.78800	0.59030	0.36530	0.0430*
H11W	1.06400	0.68180	0.60200	0.0970*
H12W	1.02500	0.45100	0.63200	0.0970*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cs1	0.0581 (3)	0.0302 (3)	0.0667 (4)	−0.0028 (2)	0.0012 (2)	0.0010 (2)
Cl2	0.0655 (12)	0.0500 (11)	0.0322 (9)	−0.0108 (9)	−0.0020 (8)	0.0071 (8)
Cl3	0.0487 (12)	0.0503 (12)	0.0787 (15)	0.0179 (9)	−0.0157 (10)	−0.0073 (11)
Cl6	0.0477 (11)	0.0492 (11)	0.0530 (11)	0.0041 (9)	−0.0016 (8)	0.0152 (9)
O1W	0.067 (4)	0.073 (4)	0.061 (3)	−0.041 (3)	0.031 (3)	−0.027 (3)
O12	0.039 (3)	0.075 (4)	0.049 (3)	−0.016 (3)	0.021 (2)	−0.026 (3)
O13	0.061 (4)	0.081 (4)	0.083 (4)	−0.042 (3)	0.041 (3)	−0.050 (4)
C1	0.025 (3)	0.026 (3)	0.031 (3)	−0.006 (3)	0.003 (2)	−0.004 (3)
C2	0.035 (4)	0.032 (3)	0.029 (3)	−0.011 (3)	−0.002 (3)	−0.004 (3)
C3	0.022 (3)	0.034 (3)	0.051 (4)	0.003 (3)	−0.006 (3)	−0.011 (3)
C4	0.032 (4)	0.051 (4)	0.039 (4)	−0.001 (3)	0.011 (3)	−0.017 (3)
C5	0.042 (4)	0.047 (4)	0.030 (3)	−0.009 (3)	0.013 (3)	−0.005 (3)
C6	0.025 (3)	0.030 (3)	0.039 (4)	−0.002 (3)	−0.004 (3)	−0.003 (3)
C11	0.035 (4)	0.035 (4)	0.038 (4)	−0.003 (3)	0.010 (3)	−0.010 (3)
C12	0.038 (4)	0.026 (3)	0.029 (3)	0.001 (3)	0.008 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Cs1—Cl6	3.711 (2)	O1W—H12W	0.8400
Cs1—O1W	3.131 (6)	C1—C2	1.392 (9)
Cs1—O13	3.246 (7)	C1—C11	1.496 (9)
Cs1—Cl6ⁱ	3.646 (2)	C1—C6	1.392 (9)
Cs1—O1Wⁱ	3.148 (6)	C2—C3	1.387 (9)
Cs1—O12ⁱⁱ	3.213 (5)	C3—C4	1.365 (10)
Cs1—O12ⁱⁱⁱ	3.103 (6)	C4—C5	1.382 (10)
Cs1—O12^iv	3.242 (6)	C5—C6	1.385 (10)
Cl2—C2	1.727 (6)	C11—C12	1.527 (10)
Cl3—C3	1.732 (7)	C4—H4	0.9300
Cl6—C6	1.737 (7)	C5—H5	0.9300
O12—C12	1.244 (8)	C11—H11A	0.9700
O13—C12	1.235 (9)	C11—H11B	0.9700
O1W—H11W	0.9700

Cl6—Cs1—O1W	73.58 (10)	Cs1ⁱⁱ—O12—Cs1^vi	89.15 (14)
Cl6—Cs1—O13	62.95 (11)	Cs1ⁱⁱ—O12—Cs1^vii	86.76 (13)
Cl6—Cs1—Cl6ⁱ	85.27 (4)	Cs1^vi—O12—Cs1^vii	103.50 (16)
Cl6—Cs1—O1Wⁱ	143.35 (11)	Cs1—O13—C12	141.3 (5)
Cl6—Cs1—O12ⁱⁱ	136.07 (11)	Cs1—O1W—H12W	126.00
Cl6—Cs1—O12ⁱⁱⁱ	64.54 (11)	H11W—O1W—H12W	103.00
Cl6—Cs1—O12^iv	129.83 (10)	Cs1—O1W—H11W	95.00
O1W—Cs1—O13	80.93 (15)	Cs1^v—O1W—H11W	149.00
Cl6ⁱ—Cs1—O1W	142.70 (11)	C2—C1—C11	122.6 (5)
O1W—Cs1—O1Wⁱ	105.07 (14)	C6—C1—C11	121.8 (5)
O1W—Cs1—O12ⁱⁱ	62.90 (14)	C2—C1—C6	115.6 (5)
O1W—Cs1—O12ⁱⁱⁱ	69.09 (14)	Cl2—C2—C1	118.2 (5)
O1W—Cs1—O12^iv	151.22 (14)	Cl2—C2—C3	119.7 (5)
Cl6ⁱ—Cs1—O13	62.00 (11)	C1—C2—C3	122.1 (5)
O1Wⁱ—Cs1—O13	80.54 (15)	C2—C3—C4	120.4 (6)
O12ⁱⁱ—Cs1—O13	113.08 (14)	Cl3—C3—C4	118.6 (5)
O12ⁱⁱⁱ—Cs1—O13	124.78 (15)	Cl3—C3—C2	121.0 (5)
O12^iv—Cs1—O13	122.59 (15)	C3—C4—C5	119.7 (6)
Cl6ⁱ—Cs1—O1Wⁱ	74.34 (10)	C4—C5—C6	119.1 (6)
Cl6ⁱ—Cs1—O12ⁱⁱ	134.05 (11)	Cl6—C6—C5	116.7 (5)
Cl6ⁱ—Cs1—O12ⁱⁱⁱ	128.39 (10)	C1—C6—C5	123.2 (6)
Cl6ⁱ—Cs1—O12^iv	64.16 (10)	Cl6—C6—C1	120.2 (5)
O1Wⁱ—Cs1—O12ⁱⁱ	60.21 (14)	C1—C11—C12	114.1 (5)
O1Wⁱ—Cs1—O12ⁱⁱⁱ	150.59 (14)	O12—C12—C11	117.1 (6)
O1Wⁱ—Cs1—O12^iv	67.16 (14)	O13—C12—C11	118.5 (6)
O12ⁱⁱ—Cs1—O12ⁱⁱⁱ	93.30 (14)	O12—C12—O13	124.3 (7)
O12ⁱⁱ—Cs1—O12^iv	90.73 (14)	C3—C4—H4	120.00
O12ⁱⁱⁱ—Cs1—O12^iv	103.50 (15)	C5—C4—H4	120.00
Cs1—Cl6—C6	94.4 (2)	C4—C5—H5	120.00
Cs1—Cl6—Cs1^v	85.27 (4)	C6—C5—H5	120.00
Cs1^v—Cl6—C6	173.7 (2)	C1—C11—H11A	109.00
Cs1—O1W—Cs1^v	105.07 (15)	C1—C11—H11B	109.00
Cs1ⁱⁱ—O12—C12	119.0 (4)	C12—C11—H11A	109.00
Cs1^vi—O12—C12	132.9 (4)	C12—C11—H11B	109.00
Cs1^vii—O12—C12	114.3 (4)	H11A—C11—H11B	108.00

O1W—Cs1—Cl6—C6	−142.6 (3)	O1W—Cs1—O12ⁱⁱⁱ—C12ⁱⁱⁱ	−172.3 (6)
O1W—Cs1—Cl6—Cs1^v	31.08 (11)	O13—Cs1—O12ⁱⁱⁱ—Cs1^v	32.8 (2)
O13—Cs1—Cl6—C6	−54.6 (3)	O13—Cs1—O12ⁱⁱⁱ—C12ⁱⁱⁱ	−110.4 (6)
O13—Cs1—Cl6—Cs1^v	119.12 (12)	Cl6—Cs1—O12^iv—Cs1ⁱ	−112.05 (13)
Cl6ⁱ—Cs1—Cl6—C6	6.3 (2)	Cl6—Cs1—O12^iv—Cs1^viii	159.60 (5)
Cl6ⁱ—Cs1—Cl6—Cs1^v	180.00 (5)	Cl6—Cs1—O12^iv—C12^iv	39.1 (5)
O1Wⁱ—Cs1—Cl6—C6	−49.3 (3)	O1W—Cs1—O12^iv—Cs1ⁱ	109.0 (3)
O1Wⁱ—Cs1—Cl6—Cs1^v	124.40 (17)	O1W—Cs1—O12^iv—Cs1^viii	20.7 (3)
O12ⁱⁱ—Cs1—Cl6—C6	−150.5 (3)	O1W—Cs1—O12^iv—C12^iv	−99.8 (5)
O12ⁱⁱ—Cs1—Cl6—Cs1^v	23.13 (16)	O13—Cs1—O12^iv—Cs1ⁱ	−31.8 (2)
O12ⁱⁱⁱ—Cs1—Cl6—C6	143.2 (3)	O13—Cs1—O12^iv—Cs1^viii	−120.17 (14)
O12ⁱⁱⁱ—Cs1—Cl6—Cs1^v	−43.15 (11)	O13—Cs1—O12^iv—C12^iv	119.3 (4)
O12^iv—Cs1—Cl6—C6	56.6 (3)	Cs1—Cl6—C6—C1	89.9 (5)
O12^iv—Cs1—Cl6—Cs1^v	−129.68 (13)	Cs1—Cl6—C6—C5	−90.0 (5)
Cl6—Cs1—O1W—Cs1^v	−38.11 (11)	Cs1^vi—O12—C12—O13	153.4 (5)
O13—Cs1—O1W—Cs1^v	−102.44 (17)	Cs1^vii—O12—C12—O13	−66.4 (8)
Cl6ⁱ—Cs1—O1W—Cs1^v	−96.19 (19)	Cs1ⁱⁱ—O12—C12—C11	−142.5 (5)
O1Wⁱ—Cs1—O1W—Cs1^v	180.00 (15)	Cs1^vi—O12—C12—C11	−23.0 (9)
O12ⁱⁱ—Cs1—O1W—Cs1^v	135.7 (2)	Cs1^vii—O12—C12—C11	117.2 (5)
O12ⁱⁱⁱ—Cs1—O1W—Cs1^v	30.36 (15)	Cs1ⁱⁱ—O12—C12—O13	33.9 (9)
O12^iv—Cs1—O1W—Cs1^v	110.2 (3)	Cs1—O13—C12—O12	−107.6 (8)
Cl6—Cs1—O13—C12	−39.5 (7)	Cs1—O13—C12—C11	68.8 (9)
O1W—Cs1—O13—C12	36.7 (7)	C6—C1—C2—C3	−0.5 (9)
Cl6ⁱ—Cs1—O13—C12	−139.1 (7)	C11—C1—C2—Cl2	0.7 (8)
O1Wⁱ—Cs1—O13—C12	143.7 (7)	C6—C1—C2—Cl2	179.8 (5)
O12ⁱⁱ—Cs1—O13—C12	92.0 (7)	C2—C1—C6—Cl6	−178.8 (5)
O12ⁱⁱⁱ—Cs1—O13—C12	−19.9 (8)	C2—C1—C6—C5	1.1 (9)
O12^iv—Cs1—O13—C12	−161.3 (7)	C11—C1—C2—C3	−179.6 (6)
Cl6—Cs1—Cl6ⁱ—Cs1ⁱ	180.00 (4)	C11—C1—C6—Cl6	0.3 (9)
O1W—Cs1—Cl6ⁱ—Cs1ⁱ	−125.21 (17)	C11—C1—C6—C5	−179.8 (6)
O13—Cs1—Cl6ⁱ—Cs1ⁱ	−118.22 (12)	C2—C1—C11—C12	85.3 (7)
Cl6—Cs1—O1Wⁱ—Cs1ⁱ	97.39 (19)	C6—C1—C11—C12	−93.7 (7)
O1W—Cs1—O1Wⁱ—Cs1ⁱ	179.98 (16)	Cl2—C2—C3—Cl3	0.2 (8)
O13—Cs1—O1Wⁱ—Cs1ⁱ	102.15 (17)	Cl2—C2—C3—C4	179.9 (6)
Cl6—Cs1—O12ⁱⁱ—Cs1^viii	−157.48 (7)	C1—C2—C3—Cl3	−179.6 (5)
Cl6—Cs1—O12ⁱⁱ—C12ⁱⁱ	62.1 (5)	C1—C2—C3—C4	0.2 (10)
O1W—Cs1—O12ⁱⁱ—Cs1^viii	−166.04 (19)	C2—C3—C4—C5	−0.5 (11)
O1W—Cs1—O12ⁱⁱ—C12ⁱⁱ	53.6 (5)	Cl3—C3—C4—C5	179.2 (6)
O13—Cs1—O12ⁱⁱ—Cs1^viii	128.20 (15)	C3—C4—C5—C6	1.1 (11)
O13—Cs1—O12ⁱⁱ—C12ⁱⁱ	−12.2 (5)	C4—C5—C6—Cl6	178.4 (6)
Cl6—Cs1—O12ⁱⁱⁱ—Cs1^v	52.02 (11)	C4—C5—C6—C1	−1.5 (11)
Cl6—Cs1—O12ⁱⁱⁱ—C12ⁱⁱⁱ	−91.1 (6)	C1—C11—C12—O12	−160.0 (6)
O1W—Cs1—O12ⁱⁱⁱ—Cs1^v	−29.16 (14)	C1—C11—C12—O13	23.4 (9)

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+2, −z+1; (iii) x, −y+3/2, z+1/2; (iv) x, −y+5/2, z+1/2; (v) x, y−1, z; (vi) x, −y+3/2, z−1/2; (vii) x, −y+5/2, z−1/2; (viii) −x+2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O13ⁱⁱ	0.97	1.70	2.638 (8)	161
O1W—H12W···O12^ix	0.84	2.40	3.191 (8)	158
C11—H11A···Cl2	0.97	2.64	3.026 (7)	104
C11—H11B···Cl6	0.97	2.61	3.062 (7)	109

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

Selected bond lengths (Å) top

Cs1—Cl6	3.711 (2)	Cs1—O1Wⁱ	3.148 (6)
Cs1—O1W	3.131 (6)	Cs1—O12ⁱⁱ	3.213 (5)
Cs1—O13	3.246 (7)	Cs1—O12ⁱⁱⁱ	3.103 (6)
Cs1—Cl6ⁱ	3.646 (2)	Cs1—O12^iv	3.242 (6)

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+2, −z+1; (iii) x, −y+3/2, z+1/2; (iv) x, −y+5/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O13ⁱⁱ	0.97	1.70	2.638 (8)	161
O1W—H12W···O12^v	0.84	2.40	3.191 (8)	158

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

Acknowledgements

The author acknowledges financial support from the Science and Engineering Faculty and the University Library, Queensland University of Technology.

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