Poly[μ-aqua-μ5-[2-(2,3,6-tri-chloro-phenyl)acetato]-caesium].

In the structure of the title complex, [Cs(C8H4Cl3O2)(H2O)] n , the caesium salt of the commercial herbicide fenac [(2,3,6-tri-chloro-phen-yl)acetic acid], the irregular eight-coordination about Cs(+) comprises a bidentate O:Cl-chelate inter-action involving a carboxyl-ate-O atom and an ortho-related ring-substituted Cl atom, which is also bridging, a triple-bridging carboxyl-ate-O atom and a bridging water mol-ecule. A two-dimensional polymer is generated, lying parallel to (100), within which there are water-carboxyl-ate O-H⋯O hy-dro-gen-bonding inter-actions.

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 = 389.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.111

S = 1.09

2284 reflections

136 parameters

H-atom parameters constrained

Δρmax = 2.18 e Å−3

Δρmin = −1.86 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029395/wm2781sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029395/wm2781Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cs(C8H4Cl3O2)(H2O)]	F(000) = 736
Mr = 389.39	Dx = 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

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	Rint = 0.034
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −20→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
Tmin = 0.582, Tmax = 0.980	l = −17→12
7585 measured reflections

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(Fo2) + (0.0285P)2 + 9.056P] where P = (Fo2 + 2Fc2)/3
2284 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 2.18 e Å−3
0 restraints	Δρmin = −1.86 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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—O12iv	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—Cs1vi	89.15 (14)
Cl6—Cs1—O13	62.95 (11)	Cs1ii—O12—Cs1vii	86.76 (13)
Cl6—Cs1—Cl6i	85.27 (4)	Cs1vi—O12—Cs1vii	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—O12iv	129.83 (10)	Cs1—O1W—H11W	95.00
O1W—Cs1—O13	80.93 (15)	Cs1v—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—O12iv	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)
O12iv—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—O12iv	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—O12iv	67.16 (14)	O13—C12—C11	118.5 (6)
O12ii—Cs1—O12iii	93.30 (14)	O12—C12—O13	124.3 (7)
O12ii—Cs1—O12iv	90.73 (14)	C3—C4—H4	120.00
O12iii—Cs1—O12iv	103.50 (15)	C5—C4—H4	120.00
Cs1—Cl6—C6	94.4 (2)	C4—C5—H5	120.00
Cs1—Cl6—Cs1v	85.27 (4)	C6—C5—H5	120.00
Cs1v—Cl6—C6	173.7 (2)	C1—C11—H11A	109.00
Cs1—O1W—Cs1v	105.07 (15)	C1—C11—H11B	109.00
Cs1ii—O12—C12	119.0 (4)	C12—C11—H11A	109.00
Cs1vi—O12—C12	132.9 (4)	C12—C11—H11B	109.00
Cs1vii—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—Cs1v	31.08 (11)	O13—Cs1—O12iii—Cs1v	32.8 (2)
O13—Cs1—Cl6—C6	−54.6 (3)	O13—Cs1—O12iii—C12iii	−110.4 (6)
O13—Cs1—Cl6—Cs1v	119.12 (12)	Cl6—Cs1—O12iv—Cs1i	−112.05 (13)
Cl6i—Cs1—Cl6—C6	6.3 (2)	Cl6—Cs1—O12iv—Cs1viii	159.60 (5)
Cl6i—Cs1—Cl6—Cs1v	180.00 (5)	Cl6—Cs1—O12iv—C12iv	39.1 (5)
O1Wi—Cs1—Cl6—C6	−49.3 (3)	O1W—Cs1—O12iv—Cs1i	109.0 (3)
O1Wi—Cs1—Cl6—Cs1v	124.40 (17)	O1W—Cs1—O12iv—Cs1viii	20.7 (3)
O12ii—Cs1—Cl6—C6	−150.5 (3)	O1W—Cs1—O12iv—C12iv	−99.8 (5)
O12ii—Cs1—Cl6—Cs1v	23.13 (16)	O13—Cs1—O12iv—Cs1i	−31.8 (2)
O12iii—Cs1—Cl6—C6	143.2 (3)	O13—Cs1—O12iv—Cs1viii	−120.17 (14)
O12iii—Cs1—Cl6—Cs1v	−43.15 (11)	O13—Cs1—O12iv—C12iv	119.3 (4)
O12iv—Cs1—Cl6—C6	56.6 (3)	Cs1—Cl6—C6—C1	89.9 (5)
O12iv—Cs1—Cl6—Cs1v	−129.68 (13)	Cs1—Cl6—C6—C5	−90.0 (5)
Cl6—Cs1—O1W—Cs1v	−38.11 (11)	Cs1vi—O12—C12—O13	153.4 (5)
O13—Cs1—O1W—Cs1v	−102.44 (17)	Cs1vii—O12—C12—O13	−66.4 (8)
Cl6i—Cs1—O1W—Cs1v	−96.19 (19)	Cs1ii—O12—C12—C11	−142.5 (5)
O1Wi—Cs1—O1W—Cs1v	180.00 (15)	Cs1vi—O12—C12—C11	−23.0 (9)
O12ii—Cs1—O1W—Cs1v	135.7 (2)	Cs1vii—O12—C12—C11	117.2 (5)
O12iii—Cs1—O1W—Cs1v	30.36 (15)	Cs1ii—O12—C12—O13	33.9 (9)
O12iv—Cs1—O1W—Cs1v	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)
O12iv—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—Cs1viii	−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—Cs1viii	−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—Cs1viii	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—Cs1v	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—Cs1v	−29.16 (14)	C1—C11—C12—O13	23.4 (9)

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···O12ix	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

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—O1W i	3.148 (6)
Cs1—O12ii	3.213 (5)
Cs1—O12iii	3.103 (6)
Cs1—O12iv	3.242 (6)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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⋯O12v	0.84	2.40	3.191 (8)	158

Symmetry codes: (ii) ; (v) .