Poly[[[diaqua­cobalt(II)]-bis­[μ2-1,1′-(butane-1,4-di­yl)diimidazole-κ2N3:N3′]] dichloride tetra­hydrate]

Su, Y.; Hou, Y.-J.; Sun, Z.-Z.; Hou, G.-F.; Gao, J.-S.

doi:10.1107/S1600536809007478

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages m370-m371

doi:10.1107/S1600536809007478

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Poly[[[diaquacobalt(II)]-bis[μ₂-1,1′-(butane-1,4-diyl)diimidazole-κ²N³:N^3′]] dichloride tetrahydrate]

Yu Su,^a Yan-Jun Hou,^a Zhi-Zhong Sun,^a Guang-Feng Hou ^a and Jin-Sheng Gao ^a ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 26 February 2009; accepted 1 March 2009; online 6 March 2009)

In the title compound, {[Co(C₁₀H₁₄N₄)₂(H₂O)₂]Cl₂·4H₂O}_n, the Co^II atom and the mid-point of the 1,1′-butane-1,4-diyldiimidazole ligands lie on inversion centers. The Co^II atom is six-coordinated in a slightly distorted octahedral environment by four N atoms from four different ligands and by two O atoms from the water molecules. The Co^II atoms are bridged by the ligands into a (4,4) net. Adjacent nets are linked to the chloride anions and uncoordinated water molecules via O—H⋯Cl and O—H⋯O hydrogen bonds, generating a three-dimensional supramolecular structure.

Related literature

For the synthesis of 1,1′-butane-1,4-diyldiimidazole, see: Ma et al.(2003 ); Yu et al. (2008 ). For a related Co complex, see: Dong & Zhang (2006 ).

Experimental

Crystal data

[Co(C₁₀H₁₄N₄)₂(H₂O)₂]Cl₂·4H₂O
M_r = 618.43
Triclinic, $[P \overline 1]$
a = 7.969 (6) Å
b = 9.979 (6) Å
c = 10.259 (7) Å
α = 114.97 (2)°
β = 90.83 (3)°
γ = 93.70 (3)°
V = 737.3 (8) Å³
Z = 1
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 291 K
0.44 × 0.37 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.718, T_max = 0.842
7288 measured reflections
3348 independent reflections
3018 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.084
S = 1.14
3348 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—N1	2.1265 (18)
Co1—N3	2.1355 (18)
Co1—O1	2.1819 (17)
Symmetry code: (i) -x+1, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H15⋯O3ⁱⁱ	0.85	1.94	2.781 (2)	169
O1—H16⋯Cl1	0.85	2.35	3.1728 (19)	165
O2—H17⋯Cl1ⁱⁱ	0.85	2.32	3.172 (2)	176
O2—H18⋯Cl1ⁱⁱⁱ	0.85	2.44	3.292 (3)	175
O3—H19⋯O2	0.85	1.99	2.829 (3)	171
O3—H20⋯Cl1	0.85	2.41	3.261 (3)	174
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007478/ng2551sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007478/ng2551Isup2.hkl

checkCIF report

Comment top

The L molecules as a flexible ligand exhibit a variety of supramolecular aggregation patterns (Ma et al., 2003; Dong et al., 2006; Yu et al., 2008). In this paper, we report the new title compound, (I), synthssized by the reaction of L molecules and cobalt dichloride in aqua solution.

In (I), each Co^II atom is located on a inversion centre and is six-coordinated in an octahedral environment by four N atoms from four different L molecules and two O atoms form the two water molecules (Fig. 1). The Co—N and Co—O distances are normal (Table 1). The Co^II atoms are bridged by ligands, generating a two-dimensional (4,4)-network (Fig. 2).

The hydrogen bonding cluster, containing the O—H···Cl and O—H···O hydrogen bonding interaction between the chloride anions, uncoordinated water molecules and the coordinated water molecules (Fig. 3), which linke the adjacent fishnet planes to a three-dimensional supramolecular structure (Fig. 4, Table 2).

Related literature top

For the synthesis of 1,1'-butane-1,4-diyldiimidazole, see: Ma et al.(2003); Yu et al. (2008). For a related Co complex, see: Dong & Zhang (2006).

Experimental top

L was prepared from imidazole and 1,4-dibromobutane in DMSO (Ma et al., 2003). L (0.76 g, 4 mmol) and cobalt dichloride (0.51 g, 4 mmol) were dissolved in hot aqua solution (10 ml) to give a clear solution. The resulting solution was allowed to stand in a desiccator at room temperature for a week, red crystals of (I) were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku 1998); cell refinement: RAPID-AUTO (Rigaku 1998); data reduction: CrystalStructure (Rigaku/MSC 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms. Dashed lines indicate the hydrogen-bonding interactions [Symmetry code; (I) -x + 1, -y + 1, -z + 1; (II) -x + 2, -y, -z + 2: (III) -x, -y + 1, -z + 2]
	Fig. 2. A partial packing view, showing the two-dimensional (4,4)-network. C-bond H atoms have beeb omitted.
	Fig. 3. A showing of the hydrogen bonding cluster in I.
	Fig. 4. A Partial packing view, shoving the three-dimensional supramolecular structure. Dashed lines indicate the hydrogen-bonding interactions and no involving H atoms have beeb omitted.

Poly[[[diaquacobalt(II)]-bis[µ₂-1,1'-(butane-1,4-diyl)diimidazole- κ²N³:N^3']] dichloride tetrahydrate] top

Crystal data top

[Co(C₁₀H₁₄N₄)₂(H₂O)₂]Cl₂·4H₂O	Z = 1
M_r = 618.43	F(000) = 325
Triclinic, P1	D_x = 1.393 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.969 (6) Å	Cell parameters from 6505 reflections
b = 9.979 (6) Å	θ = 3.3–27.5°
c = 10.259 (7) Å	µ = 0.81 mm⁻¹
α = 114.97 (2)°	T = 291 K
β = 90.83 (3)°	Block, red
γ = 93.70 (3)°	0.44 × 0.37 × 0.22 mm
V = 737.3 (8) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3348 independent reflections
Radiation source: fine-focus sealed tube	3018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scan	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.718, T_max = 0.842	k = −12→12
7288 measured reflections	l = −13→13

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0444P)² + 0.1566P] where P = (F_o² + 2F_c²)/3
3348 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Co(C₁₀H₁₄N₄)₂(H₂O)₂]Cl₂·4H₂O	γ = 93.70 (3)°
M_r = 618.43	V = 737.3 (8) Å³
Triclinic, P1	Z = 1
a = 7.969 (6) Å	Mo Kα radiation
b = 9.979 (6) Å	µ = 0.81 mm⁻¹
c = 10.259 (7) Å	T = 291 K
α = 114.97 (2)°	0.44 × 0.37 × 0.22 mm
β = 90.83 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3348 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3018 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.842	R_int = 0.017
7288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.14	Δρ_max = 0.33 e Å⁻³
3348 reflections	Δρ_min = −0.23 e Å⁻³
169 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
C1	0.6521 (2)	0.1455 (2)	0.94674 (17)	0.0354 (4)
H1	0.6695	0.2157	1.0416	0.043*
C2	0.5873 (2)	0.16729 (19)	0.83506 (17)	0.0330 (3)
H2	0.5516	0.2565	0.8409	0.040*
C3	0.64306 (19)	−0.06103 (17)	0.75067 (16)	0.0283 (3)
H3	0.6543	−0.1596	0.6885	0.034*
C4	0.7646 (2)	−0.0765 (2)	0.9698 (2)	0.0382 (4)
H4	0.7167	−0.1783	0.9312	0.046*
H5	0.7386	−0.0288	1.0705	0.046*
C5	0.9543 (2)	−0.07561 (17)	0.95821 (18)	0.0335 (3)
H6	0.9958	−0.1443	0.9931	0.040*
H7	0.9803	−0.1107	0.8576	0.040*
C6	0.2259 (2)	0.22255 (18)	0.64249 (18)	0.0331 (3)
H8	0.2873	0.2993	0.6314	0.040*
C7	0.1451 (2)	0.00888 (18)	0.63070 (18)	0.0325 (3)
H9	0.1409	−0.0916	0.6093	0.039*
C8	0.0303 (2)	0.10224 (18)	0.70471 (18)	0.0344 (4)
H10	−0.0658	0.0784	0.7432	0.041*
C9	0.0058 (2)	0.3775 (2)	0.7958 (2)	0.0406 (4)
H11	−0.1151	0.3629	0.7760	0.049*
H12	0.0495	0.4529	0.7663	0.049*
C10	0.0423 (3)	0.43001 (19)	0.9552 (2)	0.0438 (4)
H13	0.1630	0.4487	0.9751	0.053*
H14	0.0038	0.3522	0.9832	0.053*
Cl1	0.74821 (7)	0.35621 (5)	0.32791 (5)	0.04818 (14)
Co1	0.5000	0.0000	0.5000	0.02144 (9)
N1	0.58238 (16)	0.03688 (14)	0.71136 (13)	0.0274 (3)
N2	0.68668 (16)	−0.00004 (15)	0.89242 (14)	0.0299 (3)
N3	0.26947 (15)	0.08534 (14)	0.59164 (13)	0.0265 (3)
N4	0.08195 (17)	0.23842 (15)	0.71246 (15)	0.0312 (3)
O1	0.59361 (16)	0.22377 (12)	0.53595 (13)	0.0381 (3)
H15	0.5827	0.3049	0.6089	0.057*
H16	0.6273	0.2429	0.4670	0.057*
O2	0.1615 (2)	0.38041 (17)	0.36469 (18)	0.0668 (5)
H17	0.1812	0.4490	0.4489	0.100*
H18	0.0554	0.3700	0.3490	0.100*
O3	0.4231 (2)	0.49280 (17)	0.24618 (19)	0.0670 (5)
H19	0.3378	0.4575	0.2734	0.100*
H20	0.5121	0.4639	0.2693	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0329 (8)	0.0426 (9)	0.0241 (7)	0.0052 (7)	0.0005 (6)	0.0074 (7)
C2	0.0328 (8)	0.0345 (8)	0.0280 (7)	0.0091 (6)	0.0016 (6)	0.0086 (7)
C3	0.0268 (7)	0.0319 (8)	0.0256 (7)	0.0010 (6)	−0.0018 (6)	0.0120 (6)
C4	0.0357 (9)	0.0503 (10)	0.0395 (9)	−0.0060 (7)	−0.0089 (7)	0.0314 (8)
C5	0.0354 (9)	0.0321 (8)	0.0369 (8)	0.0016 (6)	−0.0083 (7)	0.0188 (7)
C6	0.0291 (8)	0.0340 (8)	0.0418 (9)	0.0078 (6)	0.0106 (7)	0.0205 (7)
C7	0.0335 (8)	0.0283 (8)	0.0337 (8)	0.0033 (6)	0.0067 (6)	0.0110 (7)
C8	0.0306 (8)	0.0358 (8)	0.0378 (8)	0.0041 (6)	0.0110 (7)	0.0161 (7)
C9	0.0412 (10)	0.0369 (9)	0.0508 (10)	0.0190 (7)	0.0179 (8)	0.0228 (8)
C10	0.0513 (11)	0.0324 (9)	0.0497 (11)	0.0197 (8)	0.0149 (9)	0.0166 (8)
Cl1	0.0565 (3)	0.0506 (3)	0.0353 (2)	−0.0058 (2)	0.0008 (2)	0.0175 (2)
Co1	0.02117 (15)	0.02402 (15)	0.01902 (14)	0.00459 (10)	0.00162 (10)	0.00862 (11)
N1	0.0255 (6)	0.0329 (7)	0.0226 (6)	0.0051 (5)	0.0004 (5)	0.0104 (5)
N2	0.0247 (6)	0.0420 (7)	0.0260 (6)	0.0001 (5)	−0.0020 (5)	0.0179 (6)
N3	0.0235 (6)	0.0316 (6)	0.0256 (6)	0.0061 (5)	0.0038 (5)	0.0127 (5)
N4	0.0290 (7)	0.0328 (7)	0.0353 (7)	0.0105 (5)	0.0103 (5)	0.0166 (6)
O1	0.0505 (8)	0.0261 (6)	0.0355 (6)	0.0007 (5)	0.0115 (5)	0.0110 (5)
O2	0.0597 (10)	0.0521 (9)	0.0657 (10)	0.0088 (7)	−0.0033 (8)	0.0025 (8)
O3	0.0763 (12)	0.0472 (9)	0.0683 (10)	0.0111 (8)	0.0051 (9)	0.0147 (8)

Geometric parameters (Å, º) top

C1—C2	1.354 (3)	C8—N4	1.363 (2)
C1—N2	1.367 (2)	C8—H10	0.9300
C1—H1	0.9300	C9—N4	1.466 (2)
C2—N1	1.380 (2)	C9—C10	1.508 (3)
C2—H2	0.9300	C9—H11	0.9700
C3—N1	1.319 (2)	C9—H12	0.9700
C3—N2	1.348 (2)	C10—C10ⁱⁱ	1.518 (3)
C3—H3	0.9300	C10—H13	0.9700
C4—N2	1.468 (2)	C10—H14	0.9700
C4—C5	1.518 (3)	Co1—N1ⁱⁱⁱ	2.1265 (18)
C4—H4	0.9700	Co1—N1	2.1265 (18)
C4—H5	0.9700	Co1—N3	2.1355 (18)
C5—C5ⁱ	1.513 (3)	Co1—N3ⁱⁱⁱ	2.1355 (18)
C5—H6	0.9700	Co1—O1	2.1819 (17)
C5—H7	0.9700	Co1—O1ⁱⁱⁱ	2.1819 (17)
C6—N3	1.316 (2)	O1—H15	0.8500
C6—N4	1.345 (2)	O1—H16	0.8501
C6—H8	0.9300	O2—H17	0.8501
C7—C8	1.347 (2)	O2—H18	0.8499
C7—N3	1.378 (2)	O3—H19	0.8500
C7—H9	0.9300	O3—H20	0.8501

C2—C1—N2	106.40 (14)	C9—C10—H13	109.1
C2—C1—H1	126.8	C10ⁱⁱ—C10—H13	109.1
N2—C1—H1	126.8	C9—C10—H14	109.1
C1—C2—N1	109.55 (16)	C10ⁱⁱ—C10—H14	109.1
C1—C2—H2	125.2	H13—C10—H14	107.8
N1—C2—H2	125.2	N1ⁱⁱⁱ—Co1—N1	180.0
N1—C3—N2	111.34 (14)	N1ⁱⁱⁱ—Co1—N3	93.49 (6)
N1—C3—H3	124.3	N1—Co1—N3	86.51 (6)
N2—C3—H3	124.3	N1ⁱⁱⁱ—Co1—N3ⁱⁱⁱ	86.51 (6)
N2—C4—C5	112.55 (14)	N1—Co1—N3ⁱⁱⁱ	93.49 (6)
N2—C4—H4	109.1	N3—Co1—N3ⁱⁱⁱ	180.0
C5—C4—H4	109.1	N1ⁱⁱⁱ—Co1—O1	88.40 (6)
N2—C4—H5	109.1	N1—Co1—O1	91.60 (6)
C5—C4—H5	109.1	N3—Co1—O1	88.99 (6)
H4—C4—H5	107.8	N3ⁱⁱⁱ—Co1—O1	91.01 (6)
C5ⁱ—C5—C4	113.60 (19)	N1ⁱⁱⁱ—Co1—O1ⁱⁱⁱ	91.60 (6)
C5ⁱ—C5—H6	108.8	N1—Co1—O1ⁱⁱⁱ	88.40 (6)
C4—C5—H6	108.8	N3—Co1—O1ⁱⁱⁱ	91.01 (6)
C5ⁱ—C5—H7	108.8	N3ⁱⁱⁱ—Co1—O1ⁱⁱⁱ	88.99 (6)
C4—C5—H7	108.8	O1—Co1—O1ⁱⁱⁱ	180.0
H6—C5—H7	107.7	C3—N1—C2	105.50 (14)
N3—C6—N4	111.80 (15)	C3—N1—Co1	126.67 (11)
N3—C6—H8	124.1	C2—N1—Co1	127.81 (12)
N4—C6—H8	124.1	C3—N2—C1	107.20 (14)
C8—C7—N3	109.45 (15)	C3—N2—C4	125.39 (15)
C8—C7—H9	125.3	C1—N2—C4	127.34 (14)
N3—C7—H9	125.3	C6—N3—C7	105.19 (14)
C7—C8—N4	106.96 (15)	C6—N3—Co1	128.87 (11)
C7—C8—H10	126.5	C7—N3—Co1	125.19 (11)
N4—C8—H10	126.5	C6—N4—C8	106.59 (14)
N4—C9—C10	111.41 (14)	C6—N4—C9	126.86 (15)
N4—C9—H11	109.3	C8—N4—C9	126.17 (14)
C10—C9—H11	109.3	Co1—O1—H15	128.5
N4—C9—H12	109.3	Co1—O1—H16	121.2
C10—C9—H12	109.3	H15—O1—H16	108.9
H11—C9—H12	108.0	H17—O2—H18	106.8
C9—C10—C10ⁱⁱ	112.6 (2)	H19—O3—H20	109.6

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H15···O3^iv	0.85	1.94	2.781 (2)	169
O1—H16···Cl1	0.85	2.35	3.1728 (19)	165
O2—H17···Cl1^iv	0.85	2.32	3.172 (2)	176
O2—H18···Cl1^v	0.85	2.44	3.292 (3)	175
O3—H19···O2	0.85	1.99	2.829 (3)	171
O3—H20···Cl1	0.85	2.41	3.261 (3)	174

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₁₄N₄)₂(H₂O)₂]Cl₂·4H₂O
M_r	618.43
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.969 (6), 9.979 (6), 10.259 (7)
α, β, γ (°)	114.97 (2), 90.83 (3), 93.70 (3)
V (Å³)	737.3 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.44 × 0.37 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.718, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	7288, 3348, 3018
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.084, 1.14
No. of reflections	3348
No. of parameters	169
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

Computer programs: RAPID-AUTO (Rigaku 1998), CrystalStructure (Rigaku/MSC 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—N1	2.1265 (18)	Co1—O1	2.1819 (17)
Co1—N3	2.1355 (18)

N1ⁱ—Co1—N1	180.0	N1—Co1—O1	91.60 (6)
N1—Co1—N3	86.51 (6)	N3—Co1—O1	88.99 (6)
N3—Co1—N3ⁱ	180.0	N1—Co1—O1ⁱ	88.40 (6)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H15···O3ⁱⁱ	0.85	1.94	2.781 (2)	169.3
O1—H16···Cl1	0.85	2.35	3.1728 (19)	164.5
O2—H17···Cl1ⁱⁱ	0.85	2.32	3.172 (2)	175.6
O2—H18···Cl1ⁱⁱⁱ	0.85	2.44	3.292 (3)	174.6
O3—H19···O2	0.85	1.99	2.829 (3)	170.8
O3—H20···Cl1	0.85	2.41	3.261 (3)	173.8

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

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20872030), the Research Foundation of Heilongjiang Provincial Education Department (grant Nos. 11513073), the Project of the Special Fund of the Science and Technology Innovation People of Harbin (grant Nos. RC2006QN018001) and Heilongjiang University.

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