Triaqua­chlorido(18-crown-6)barium chloride

Zhao, M.-M.

doi:10.1107/S1600536812004990

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m286

doi:10.1107/S1600536812004990

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Triaquachlorido(18-crown-6)barium chloride

Min-Min Zhao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chemcrystal66@yahoo.com.cn

(Received 24 January 2012; accepted 5 February 2012; online 10 February 2012)

In the title compound, [BaCl(C₁₂H₂₄O₆)(H₂O)₃]Cl, the Ba^II atom, the coordinating and free Cl⁻ anions, one coordinating water molecule and two O atoms of an 18-crown-6 molecule lie on a mirror plane. The environment of the ten-coordinate Ba²⁺ ion is defined by one Cl atom, three water molecules and six O atoms from the macrocyclic ether. The macrocycle adopts a conformation with an approximate D_3d symmetry. In the crystal, O—H⋯Cl hydrogen bonds link the complex cations and Cl⁻ anions into a two-dimensional network parallel to (010). An intramolecular O—H⋯Cl hydrogen bond is also present.

Related literature

For the properties and structures of related compounds, see: Fu et al. (2007 , 2008 , 2009 ); Fu & Xiong (2008 ). For the ferroelectric properties of related derivatives, see: Fu et al. (2011a ,b ); Fu, Zhang, Cai, Ge et al. (2011 ).

Experimental

Crystal data

[BaCl(C₁₂H₂₄O₆)(H₂O)₃]Cl
M_r = 526.59
Orthorhombic, P n m a
a = 14.962 (3) Å
b = 13.416 (3) Å
c = 10.347 (2) Å
V = 2077.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.21 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.90, T_max = 1.00
20436 measured reflections
2478 independent reflections
2284 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.047
S = 1.20
2478 reflections
118 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯Cl1ⁱ	0.82	2.66	3.450 (3)	161
O1W—H1WB⋯Cl2ⁱⁱ	0.82	2.41	3.216 (3)	168
O2W—H2WA⋯Cl1	0.82	2.38	3.180 (2)	165
O2W—H2WB⋯Cl2	0.82	2.44	3.144 (2)	145
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004990/hy2512sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004990/hy2512Isup2.hkl

checkCIF report

Comment top

Coordination compounds have attracted more attention as phase transition dielectric materials for their applications in memory storage (Fu et al., 2007, 2008, 2009; Fu & Xiong 2008). With the purpose of obtaining phase transition crystals, various complexes have been studied and a series of new materials with organic and inorganic molecules have been elaborated (Fu et al., 2011a,b; Fu, Zhang, Cai, Ge et al., 2011). In this study, we describe the crystal structure of the title compound.

The title compound was composed of one macrocyclic 18-crown-6 ether, one Ba^II cation, three water molecules, one coordinated Cl^- anion and one uncoordinated Cl^- anion (Fig. 1). Six non-H atoms (Ba1, O1W, O1, O4, Cl1 and Cl2) and two H atoms (H1WA, H1WB) are located on a mirror plane. The ten-coordinated Ba^II environment is defined by one terminal Cl atom, three water molecules and six O atoms from the macrocyclic ether. The macrocycle adopts a conformation with an approximate D_3d symmetry, with all O—C—C—O torsion angles being gauche and alternating in sign and all C—O—C—C torsion angles being trans. The structure is stabilized by intermolecular O—H···Cl hydrogen bonds (Table 1). These hydrogen bonds link the ionic units into a two-dimensional network parallel to (0 1 0) (Fig. 2). O2W is involved in an intramolecular O2W—H2WB···Cl2 hydrogen bond.

Related literature top

For the properties and structures of related compounds, see: Fu et al. (2007, 2008, 2009); Fu & Xiong (2008). For the ferroelectric properties of related derivatives, see: Fu et al. (2011a,b); Fu, Zhang, Cai, Ge et al. (2011).

Experimental top

Commercial 18-crown-6 (6 mmol), HCl (10 mmol) and BaCl₂ (6 mmol) were dissolved in a water/EtOH (v/v 1:1) solution. The solvent was slowly evaporated in air, affording colourless block-shaped crystals of the title compound suitable for X-ray analysis.

The dielectric constant of the title compound as a function of temperature indicates that the permittivity is basically temperature-independent, suggesting that this compound should not be a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, the dielectric constant as a function of temperature also goes smoothly below 400 K, and there is no dielectric anomaly observed (dielectric constant ranging from 5.5 to 7.1).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms attached to C atoms have been omitted for clarity. [Symmetry code: (A) x, 1/2-y, z.]
	Fig. 2. The crystal packing of the title compound, showing hydrogen-bonding interactions (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.

Triaquachlorido(18-crown-6)barium chloride top

Crystal data top

[BaCl(C₁₂H₂₄O₆)(H₂O)₃]Cl	F(000) = 1056
M_r = 526.59	D_x = 1.684 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2478 reflections
a = 14.962 (3) Å	θ = 3.0–27.5°
b = 13.416 (3) Å	µ = 2.21 mm⁻¹
c = 10.347 (2) Å	T = 293 K
V = 2077.0 (7) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.15 mm

Data collection top

Rigaku Mercury2 CCD diffractometer	2478 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −19→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
T_min = 0.90, T_max = 1.00	l = −13→13
20436 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0112P)² + 1.2653P] where P = (F_o² + 2F_c²)/3
2478 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.49 e Å⁻³
4 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

[BaCl(C₁₂H₂₄O₆)(H₂O)₃]Cl	V = 2077.0 (7) Å³
M_r = 526.59	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 14.962 (3) Å	µ = 2.21 mm⁻¹
b = 13.416 (3) Å	T = 293 K
c = 10.347 (2) Å	0.30 × 0.25 × 0.15 mm

Data collection top

Rigaku Mercury2 CCD diffractometer	2478 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2284 reflections with I > 2σ(I)
T_min = 0.90, T_max = 1.00	R_int = 0.038
20436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	4 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 1.20	Δρ_max = 0.49 e Å⁻³
2478 reflections	Δρ_min = −0.80 e Å⁻³
118 parameters

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. 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 > 2sigma(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
Ba1	0.330565 (12)	0.2500	0.419354 (17)	0.02669 (6)
Cl2	0.17702 (6)	0.2500	0.19266 (9)	0.0506 (2)
Cl1	0.07097 (6)	0.2500	0.68085 (10)	0.0498 (2)
O2	0.35766 (12)	0.07191 (13)	0.56515 (16)	0.0417 (4)
O3	0.38055 (12)	0.06918 (14)	0.29713 (17)	0.0443 (4)
C1	0.33416 (19)	0.1618 (2)	0.7592 (2)	0.0520 (7)
H1A	0.3012	0.1635	0.8398	0.062*
H1B	0.3974	0.1581	0.7792	0.062*
C5	0.4373 (2)	0.0747 (3)	0.1869 (3)	0.0627 (9)
H5A	0.4323	0.0140	0.1365	0.075*
H5B	0.4990	0.0819	0.2142	0.075*
C3	0.3403 (2)	−0.01562 (19)	0.4902 (3)	0.0542 (7)
H3A	0.2785	−0.0162	0.4621	0.065*
H3B	0.3510	−0.0747	0.5419	0.065*
C2	0.30708 (19)	0.0729 (2)	0.6825 (3)	0.0516 (7)
H2A	0.3185	0.0126	0.7315	0.062*
H2B	0.2437	0.0760	0.6631	0.062*
C4	0.4007 (2)	−0.0152 (2)	0.3759 (3)	0.0574 (8)
H4A	0.4625	−0.0120	0.4042	0.069*
H4B	0.3926	−0.0760	0.3266	0.069*
C6	0.4108 (2)	0.1612 (3)	0.1076 (3)	0.0597 (9)
H6A	0.4462	0.1633	0.0291	0.072*
H6B	0.3483	0.1556	0.0836	0.072*
O1W	0.50755 (16)	0.2500	0.4986 (3)	0.0530 (7)
H1WA	0.5090	0.2500	0.5778	0.079*
H1WB	0.5557	0.2500	0.4606	0.079*
O4	0.42471 (17)	0.2500	0.1809 (2)	0.0472 (7)
O1	0.31620 (16)	0.2500	0.6863 (2)	0.0402 (6)
O2W	0.16525 (13)	0.13030 (15)	0.45333 (19)	0.0556 (5)
H2WA	0.1351	0.1514	0.5136	0.083*
H2WB	0.1453	0.1510	0.3846	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba1	0.02774 (10)	0.02935 (10)	0.02298 (9)	0.000	−0.00053 (8)	0.000
Cl2	0.0459 (5)	0.0653 (6)	0.0405 (5)	0.000	−0.0125 (4)	0.000
Cl1	0.0445 (5)	0.0589 (6)	0.0461 (5)	0.000	0.0038 (4)	0.000
O2	0.0435 (9)	0.0375 (10)	0.0443 (10)	−0.0053 (8)	−0.0036 (8)	0.0071 (8)
O3	0.0418 (10)	0.0440 (10)	0.0473 (11)	0.0074 (9)	−0.0011 (8)	−0.0128 (9)
C1	0.0523 (16)	0.075 (2)	0.0287 (12)	−0.0107 (16)	−0.0043 (13)	0.0145 (14)
C5	0.0509 (17)	0.074 (2)	0.063 (2)	0.0052 (16)	0.0121 (15)	−0.0312 (18)
C3	0.0643 (19)	0.0293 (13)	0.0690 (19)	−0.0036 (14)	−0.0141 (17)	0.0033 (13)
C2	0.0533 (16)	0.0567 (18)	0.0450 (16)	−0.0140 (14)	−0.0026 (13)	0.0209 (14)
C4	0.0602 (19)	0.0411 (16)	0.071 (2)	0.0181 (14)	−0.0164 (16)	−0.0152 (15)
C6	0.0512 (17)	0.094 (3)	0.0336 (15)	−0.0055 (17)	0.0081 (13)	−0.0204 (16)
O1W	0.0313 (13)	0.079 (2)	0.0484 (15)	0.000	0.0028 (12)	0.000
O4	0.0467 (15)	0.0683 (18)	0.0267 (13)	0.000	0.0027 (11)	0.000
O1	0.0423 (14)	0.0581 (16)	0.0203 (11)	0.000	−0.0024 (10)	0.000
O2W	0.0542 (12)	0.0543 (12)	0.0582 (12)	0.0080 (10)	0.0028 (10)	0.0049 (10)

Geometric parameters (Å, º) top

Ba1—O1	2.770 (2)	C5—H5A	0.9700
Ba1—O1W	2.772 (3)	C5—H5B	0.9700
Ba1—O3	2.8360 (18)	C3—C4	1.488 (4)
Ba1—O3ⁱ	2.8360 (18)	C3—H3A	0.9700
Ba1—O4	2.841 (2)	C3—H3B	0.9700
Ba1—O2ⁱ	2.8545 (17)	C2—H2A	0.9700
Ba1—O2	2.8545 (17)	C2—H2B	0.9700
Ba1—O2W	2.970 (2)	C4—H4A	0.9700
Ba1—O2Wⁱ	2.970 (2)	C4—H4B	0.9700
Ba1—Cl2	3.2831 (10)	C6—O4	1.427 (3)
O2—C2	1.431 (3)	C6—H6A	0.9700
O2—C3	1.431 (3)	C6—H6B	0.9700
O3—C5	1.424 (3)	O1W—H1WA	0.8201
O3—C4	1.427 (3)	O1W—H1WB	0.8201
C1—O1	1.429 (3)	O4—C6ⁱ	1.427 (3)
C1—C2	1.488 (4)	O1—C1ⁱ	1.429 (3)
C1—H1A	0.9700	O2W—H2WA	0.8200
C1—H1B	0.9700	O2W—H2WB	0.8200
C5—C6	1.476 (4)

O1—Ba1—O1W	77.25 (7)	C4—O3—Ba1	118.64 (15)
O1—Ba1—O3	117.71 (4)	O1—C1—C2	109.3 (2)
O1W—Ba1—O3	83.10 (5)	O1—C1—H1A	109.8
O1—Ba1—O3ⁱ	117.71 (4)	C2—C1—H1A	109.8
O1W—Ba1—O3ⁱ	83.10 (5)	O1—C1—H1B	109.8
O3—Ba1—O3ⁱ	117.60 (8)	C2—C1—H1B	109.8
O1—Ba1—O4	154.72 (7)	H1A—C1—H1B	108.3
O1W—Ba1—O4	77.47 (8)	O3—C5—C6	109.0 (2)
O3—Ba1—O4	58.80 (4)	O3—C5—H5A	109.9
O3ⁱ—Ba1—O4	58.80 (4)	C6—C5—H5A	109.9
O1—Ba1—O2ⁱ	58.95 (4)	O3—C5—H5B	109.9
O1W—Ba1—O2ⁱ	73.03 (4)	C6—C5—H5B	109.9
O3—Ba1—O2ⁱ	156.08 (5)	H5A—C5—H5B	108.3
O3ⁱ—Ba1—O2ⁱ	58.82 (5)	O2—C3—C4	108.5 (2)
O4—Ba1—O2ⁱ	112.86 (4)	O2—C3—H3A	110.0
O1—Ba1—O2	58.95 (4)	C4—C3—H3A	110.0
O1W—Ba1—O2	73.03 (4)	O2—C3—H3B	110.0
O3—Ba1—O2	58.82 (5)	C4—C3—H3B	110.0
O3ⁱ—Ba1—O2	156.08 (5)	H3A—C3—H3B	108.4
O4—Ba1—O2	112.86 (4)	O2—C2—C1	108.4 (2)
O2ⁱ—Ba1—O2	113.65 (7)	O2—C2—H2A	110.0
O1—Ba1—O2W	79.48 (6)	C1—C2—H2A	110.0
O1W—Ba1—O2W	139.52 (5)	O2—C2—H2B	110.0
O3—Ba1—O2W	79.04 (5)	C1—C2—H2B	110.0
O3ⁱ—Ba1—O2W	137.30 (5)	H2A—C2—H2B	108.4
O4—Ba1—O2W	121.05 (6)	O3—C4—C3	109.2 (2)
O2ⁱ—Ba1—O2W	120.55 (5)	O3—C4—H4A	109.8
O2—Ba1—O2W	66.62 (5)	C3—C4—H4A	109.8
O1—Ba1—O2Wⁱ	79.48 (5)	O3—C4—H4B	109.8
O1W—Ba1—O2Wⁱ	139.52 (5)	C3—C4—H4B	109.8
O3—Ba1—O2Wⁱ	137.30 (5)	H4A—C4—H4B	108.3
O3ⁱ—Ba1—O2Wⁱ	79.04 (5)	O4—C6—C5	108.7 (2)
O4—Ba1—O2Wⁱ	121.05 (6)	O4—C6—H6A	109.9
O2ⁱ—Ba1—O2Wⁱ	66.62 (5)	C5—C6—H6A	109.9
O2—Ba1—O2Wⁱ	120.55 (5)	O4—C6—H6B	109.9
O2W—Ba1—O2Wⁱ	65.46 (8)	C5—C6—H6B	109.9
O1—Ba1—Cl2	131.15 (5)	H6A—C6—H6B	108.3
O1W—Ba1—Cl2	151.60 (6)	Ba1—O1W—H1WA	108.7
O3—Ba1—Cl2	82.30 (4)	Ba1—O1W—H1WB	134.1
O3ⁱ—Ba1—Cl2	82.30 (4)	H1WA—O1W—H1WB	117.1
O4—Ba1—Cl2	74.13 (6)	C6—O4—C6ⁱ	113.1 (3)
O2ⁱ—Ba1—Cl2	118.48 (4)	C6—O4—Ba1	112.90 (16)
O2—Ba1—Cl2	118.48 (4)	C6ⁱ—O4—Ba1	112.90 (16)
O2W—Ba1—Cl2	60.12 (4)	C1ⁱ—O1—C1	111.9 (3)
O2Wⁱ—Ba1—Cl2	60.12 (4)	C1ⁱ—O1—Ba1	120.76 (14)
C2—O2—C3	111.8 (2)	C1—O1—Ba1	120.76 (14)
C2—O2—Ba1	111.42 (15)	Ba1—O2W—H2WA	111.2
C3—O2—Ba1	112.00 (14)	Ba1—O2W—H2WB	91.0
C5—O3—C4	111.9 (2)	H2WA—O2W—H2WB	110.1
C5—O3—Ba1	118.02 (17)

O1—Ba1—O2—C2	28.83 (15)	Ba1—O3—C4—C3	36.3 (3)
O1W—Ba1—O2—C2	113.93 (16)	O2—C3—C4—O3	−63.0 (3)
O3—Ba1—O2—C2	−153.90 (17)	O3—C5—C6—O4	63.5 (3)
O3ⁱ—Ba1—O2—C2	117.76 (18)	C5—C6—O4—C6ⁱ	173.19 (18)
O4—Ba1—O2—C2	−178.09 (15)	C5—C6—O4—Ba1	−57.1 (3)
O2ⁱ—Ba1—O2—C2	51.76 (17)	O1—Ba1—O4—C6	115.07 (19)
O2W—Ba1—O2—C2	−62.78 (15)	O1W—Ba1—O4—C6	115.07 (19)
O2Wⁱ—Ba1—O2—C2	−24.09 (16)	O3—Ba1—O4—C6	25.60 (18)
Cl2—Ba1—O2—C2	−94.34 (15)	O3ⁱ—Ba1—O4—C6	−155.5 (2)
O1—Ba1—O2—C3	154.96 (19)	O2ⁱ—Ba1—O4—C6	−179.65 (18)
O1W—Ba1—O2—C3	−119.95 (18)	O2—Ba1—O4—C6	49.8 (2)
O3—Ba1—O2—C3	−27.77 (16)	O2W—Ba1—O4—C6	−25.8 (2)
O3ⁱ—Ba1—O2—C3	−116.12 (19)	O2Wⁱ—Ba1—O4—C6	−104.06 (19)
O4—Ba1—O2—C3	−51.96 (18)	Cl2—Ba1—O4—C6	−64.93 (19)
O2ⁱ—Ba1—O2—C3	177.88 (14)	O1—Ba1—O4—C6ⁱ	−115.07 (19)
O2W—Ba1—O2—C3	63.35 (17)	O1W—Ba1—O4—C6ⁱ	−115.07 (19)
O2Wⁱ—Ba1—O2—C3	102.04 (17)	O3—Ba1—O4—C6ⁱ	155.5 (2)
Cl2—Ba1—O2—C3	31.79 (18)	O3ⁱ—Ba1—O4—C6ⁱ	−25.60 (18)
O1—Ba1—O3—C5	−143.25 (18)	O2ⁱ—Ba1—O4—C6ⁱ	−49.8 (2)
O1W—Ba1—O3—C5	−71.58 (18)	O2—Ba1—O4—C6ⁱ	179.65 (18)
O3ⁱ—Ba1—O3—C5	6.9 (2)	O2W—Ba1—O4—C6ⁱ	104.06 (19)
O4—Ba1—O3—C5	7.92 (18)	O2Wⁱ—Ba1—O4—C6ⁱ	25.8 (2)
O2ⁱ—Ba1—O3—C5	−67.9 (2)	Cl2—Ba1—O4—C6ⁱ	64.93 (19)
O2—Ba1—O3—C5	−145.89 (19)	C2—C1—O1—C1ⁱ	175.28 (16)
O2W—Ba1—O3—C5	144.92 (18)	C2—C1—O1—Ba1	−33.0 (3)
O2Wⁱ—Ba1—O3—C5	111.38 (18)	O1W—Ba1—O1—C1ⁱ	74.58 (19)
Cl2—Ba1—O3—C5	83.99 (18)	O3—Ba1—O1—C1ⁱ	149.64 (18)
O1—Ba1—O3—C4	−2.7 (2)	O3ⁱ—Ba1—O1—C1ⁱ	−0.5 (2)
O1W—Ba1—O3—C4	68.92 (19)	O4—Ba1—O1—C1ⁱ	74.58 (19)
O3ⁱ—Ba1—O3—C4	147.40 (16)	O2ⁱ—Ba1—O1—C1ⁱ	−3.11 (18)
O4—Ba1—O3—C4	148.4 (2)	O2—Ba1—O1—C1ⁱ	152.3 (2)
O2ⁱ—Ba1—O3—C4	72.6 (2)	O2W—Ba1—O1—C1ⁱ	−138.8 (2)
O2—Ba1—O3—C4	−5.39 (17)	O2Wⁱ—Ba1—O1—C1ⁱ	−72.05 (19)
O2W—Ba1—O3—C4	−74.58 (18)	Cl2—Ba1—O1—C1ⁱ	−105.42 (19)
O2Wⁱ—Ba1—O3—C4	−108.12 (18)	O1W—Ba1—O1—C1	−74.58 (19)
Cl2—Ba1—O3—C4	−135.51 (18)	O3—Ba1—O1—C1	0.5 (2)
C4—O3—C5—C6	178.0 (2)	O3ⁱ—Ba1—O1—C1	−149.64 (18)
Ba1—O3—C5—C6	−39.0 (3)	O4—Ba1—O1—C1	−74.58 (19)
C2—O2—C3—C4	−175.3 (2)	O2ⁱ—Ba1—O1—C1	−152.3 (2)
Ba1—O2—C3—C4	58.8 (2)	O2—Ba1—O1—C1	3.11 (18)
C3—O2—C2—C1	175.6 (2)	O2W—Ba1—O1—C1	72.05 (19)
Ba1—O2—C2—C1	−58.2 (2)	O2Wⁱ—Ba1—O1—C1	138.8 (2)
O1—C1—C2—O2	60.2 (3)	Cl2—Ba1—O1—C1	105.42 (19)
C5—O3—C4—C3	179.0 (2)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···Cl1ⁱⁱ	0.82	2.66	3.450 (3)	161
O1W—H1WB···Cl2ⁱⁱⁱ	0.82	2.41	3.216 (3)	168
O2W—H2WA···Cl1	0.82	2.38	3.180 (2)	165
O2W—H2WB···Cl2	0.82	2.44	3.144 (2)	145

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

Experimental details

Crystal data
Chemical formula	[BaCl(C₁₂H₂₄O₆)(H₂O)₃]Cl
M_r	526.59
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	293
a, b, c (Å)	14.962 (3), 13.416 (3), 10.347 (2)
V (Å³)	2077.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.21
Crystal size (mm)	0.30 × 0.25 × 0.15

Data collection
Diffractometer	Rigaku Mercury2 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.90, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	20436, 2478, 2284
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.047, 1.20
No. of reflections	2478
No. of parameters	118
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.80

Computer programs: CrystalClear (Rigaku, 2005), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···Cl1ⁱ	0.82	2.66	3.450 (3)	161
O1W—H1WB···Cl2ⁱⁱ	0.82	2.41	3.216 (3)	168
O2W—H2WA···Cl1	0.82	2.38	3.180 (2)	165
O2W—H2WB···Cl2	0.82	2.44	3.144 (2)	145

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

Acknowledgements

This work was supported by the Start-Up Grant of Southeast University, China.

References

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