catena-Poly[[triaqua­nickel(II)]-μ-5-carb­oxy­benzene-1,3-dicarboxyl­ato-κ2O1:O3]

Yao, X.-J.; Yuan, Q.

doi:10.1107/S1600536811035227

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages m1331-m1332

https://doi.org/10.1107/S1600536811035227

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catena-Poly[[triaquanickel(II)]-μ-5-carboxybenzene-1,3-dicarboxylato-κ²O¹:O³]

Xing-Jun Yao ^a ^* and Qian Yuan ^b

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, 252059 Liaocheng, Shandong, People's Republic of China, and ^bGuodian Liaocheng Power Co. Ltd, 252033 Liaocheng, Shandong, People's Republic of China
^*Correspondence e-mail: y_xingjun01@163.com

(Received 15 August 2011; accepted 29 August 2011; online 14 September 2011)

In the title compound, [Ni(C₉H₄O₆)(H₂O)₃]_n, the Ni^II ion has a distorted NiO₅ square-pyramidal geometry, the maximum deviation from the least-squares plane formed by the basal atoms being 0.9351 (13) Å. The basal plane is formed by two O atoms from carboxylate residues of the 5-carboxybenzene-1,3-dicarboxylate ligand and by two O atoms from water molecules. The O atom of the third water molecule is axially positioned, 1.7890 (19) Å perpendicular to the basal plane. The 5-carboxybenzene-1,3-dicarboxylate ligand bridges the metal atoms, forming a polymeric chain along the b axis. O—H⋯O hydrogen bonds between the water molecules and carboxylate groups stabilize the crystal structure.

Related literature

For the applications and stuctures of related metal complexes of 1,3,5-benzenetricarboxylic acid, see: Xia et al. (2004 ); Modec & Brencic (2005 ); Wei & Han (2005 ); Han & Wei (2005 ); Wang et al. (2005 ); Che et al. (2008 ); He et al. (2008 ); Li et al. (2008 ); Gao et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ni(C₉H₄O₆)(H₂O)₃]
M_r = 320.88
Monoclinic, P 2₁ /c
a = 6.838 (2) Å
b = 18.809 (5) Å
c = 10.705 (3) Å
β = 126.901 (14)°
V = 1101.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.81 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.613, T_max = 0.714
7973 measured reflections
1938 independent reflections
1864 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.102
S = 1.01
1938 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	1.9292 (14)
Ni1—O2W	1.9781 (17)
Ni1—O1W	1.9884 (18)
Ni1—O3W	2.2536 (16)
O6—Ni1ⁱ	1.9129 (15)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱⁱ	0.82	1.81	2.568 (2)	152
O1W—H1W⋯O3ⁱⁱⁱ	0.85	2.21	2.869 (3)	134
O1W—H2W⋯O5^iv	0.85	1.94	2.680 (2)	145
O2W—H4W⋯O5^v	0.85	1.89	2.715 (2)	165
O3W—H5W⋯O4^vi	0.85	2.03	2.778 (2)	147
O3W—H6W⋯O2^vii	0.85	2.49	3.068 (3)	126
O2W—H3W⋯O1^viii	0.85	2.34	3.123 (2)	154
Symmetry codes: (ii) x+1, y, z+1; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1; (v) -x+1, -y+1, -z+1; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (viii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035227/go2022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035227/go2022Isup2.hkl

checkCIF report

Comment top

In recent years, the construction of metal complexes based on 1,3,5-benzenetricarboxylic acid ligand has been investigated owing to their potential applications in many fields (Xia et al., 2004; Modec & Brencic, 2005; Wei & Han, 2005; Han & Wei, 2005; Wang et al., 2005; Che et al., 2008; He et al., 2008; Li et al., 2008; Gao et al., 2009). In order to search for new metal complex based on 1,3,5-benzenetricarboxylic acid ligand, the title complex, (I) was synthesized and its crystal determined (Fig. 1). The bond lengths and angles are normal (Allen et al., 1987). In the crystal structure, the HBTC ligands bridge the Ni atoms, forming a chain along the b axis (Fig. 2). O—H···O hydrogen bonds between the water molecules and carboxylate groups stabilize the structure.

Related literature top

For the applications and stuctures of related metal complexes of 1,3,5-benzenetricarboxylic acid, see: Xia et al. (2004); Modec & Brencic (2005); Wei & Han (2005); Han & Wei (2005); Wang et al. (2005); Che et al. (2008); He et al. (2008); Li et al. (2008); Gao et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of NiNO₃^.6H₂O (0.10 mmol), 1,3,5-benzenetricarboxylic acid (H3BTC, 0.10 mmol), Et₃N (0.1 ml), EtOH (2 ml) and H₂O (2 ml) was sealed in a 10 ml Tefon-lined stainless-steel reactor and then heated to 393 K for 48 h under autogenous pressure. The mixture was slowly cooled to room temperature. Green block crystals suitable for X-ray diffraction analysis were collected by filtration..

Structure description top

For the applications and stuctures of related metal complexes of 1,3,5-benzenetricarboxylic acid, see: Xia et al. (2004); Modec & Brencic (2005); Wei & Han (2005); Han & Wei (2005); Wang et al. (2005); Che et al. (2008); He et al. (2008); Li et al. (2008); Gao et al. (2009). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level [symmetry codes: (A) -x, 1/2 + y, 1/2 - z]
	Fig. 2. View of the chain structure in the title compound.

catena-Poly[[triaquanickel(II)]-µ-5-carboxybenzene-1,3-dicarboxylato- κ²O¹:O³] top

Crystal data top

[Ni(C₉H₄O₆)(H₂O)₃]	F(000) = 656
M_r = 320.88	D_x = 1.936 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6807 reflections
a = 6.838 (2) Å	θ = 2.6–27.8°
b = 18.809 (5) Å	µ = 1.81 mm⁻¹
c = 10.705 (3) Å	T = 296 K
β = 126.901 (14)°	Block, green
V = 1101.0 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1938 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.613, T_max = 0.714	k = −22→21
7973 measured reflections	l = −10→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0942P)² + 0.090P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
1938 reflections	Δρ_max = 0.32 e Å⁻³
173 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (3)

Crystal data top

[Ni(C₉H₄O₆)(H₂O)₃]	V = 1101.0 (5) Å³
M_r = 320.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.838 (2) Å	µ = 1.81 mm⁻¹
b = 18.809 (5) Å	T = 296 K
c = 10.705 (3) Å	0.30 × 0.25 × 0.20 mm
β = 126.901 (14)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1938 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1864 reflections with I > 2σ(I)
T_min = 0.613, T_max = 0.714	R_int = 0.021
7973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.01	Δρ_max = 0.32 e Å⁻³
1938 reflections	Δρ_min = −0.38 e Å⁻³
173 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	0.1199 (3)	0.63000 (10)	0.3748 (2)	0.0228 (4)
C2	0.2227 (3)	0.56454 (10)	0.4747 (2)	0.0203 (4)
C3	0.3935 (3)	0.57173 (10)	0.6364 (2)	0.0213 (4)
H3	0.4431	0.6168	0.6806	0.026*
C4	0.4892 (3)	0.51227 (11)	0.7312 (2)	0.0220 (4)
C5	0.4154 (3)	0.44487 (11)	0.6640 (2)	0.0231 (4)
H5	0.4805	0.4047	0.7273	0.028*
C6	0.2465 (3)	0.43711 (10)	0.5040 (2)	0.0196 (4)
C7	0.1480 (3)	0.49745 (10)	0.4085 (2)	0.0209 (4)
H7	0.0327	0.4925	0.3010	0.025*
C8	0.6645 (4)	0.51904 (11)	0.9031 (2)	0.0281 (5)
C9	0.1625 (3)	0.36441 (10)	0.4346 (2)	0.0214 (4)
Ni1	0.11091 (4)	0.773616 (12)	0.32089 (3)	0.01894 (19)
O1	0.2116 (3)	0.68864 (7)	0.44634 (16)	0.0274 (4)
O2	−0.0451 (3)	0.62603 (8)	0.23299 (18)	0.0408 (4)
O3	0.7481 (3)	0.58432 (8)	0.95119 (18)	0.0371 (4)
H3A	0.8391	0.5853	1.0470	0.056*
O4	0.7292 (4)	0.47053 (9)	0.99436 (19)	0.0532 (6)
O5	0.2577 (3)	0.31100 (8)	0.51934 (18)	0.0314 (4)
O6	−0.0066 (3)	0.36214 (7)	0.28913 (17)	0.0304 (4)
O1W	−0.1375 (4)	0.78863 (9)	0.3587 (2)	0.0448 (5)
H1W	−0.0823	0.8266	0.4123	0.067*
H2W	−0.1097	0.7563	0.4230	0.067*
O2W	0.3070 (3)	0.74742 (11)	0.2478 (2)	0.0430 (4)
H4W	0.4388	0.7241	0.3076	0.065*
H3W	0.3268	0.7712	0.1886	0.065*
O3W	0.4158 (3)	0.82950 (8)	0.53994 (18)	0.0394 (4)
H5W	0.4312	0.8744	0.5432	0.059*
H6W	0.5507	0.8132	0.5647	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0263 (9)	0.0193 (10)	0.0166 (9)	0.0008 (7)	0.0096 (7)	−0.0008 (8)
C2	0.0241 (9)	0.0153 (10)	0.0193 (9)	−0.0015 (7)	0.0119 (8)	0.0002 (7)
C3	0.0246 (9)	0.0140 (10)	0.0209 (9)	−0.0032 (7)	0.0113 (8)	−0.0021 (8)
C4	0.0240 (10)	0.0193 (9)	0.0181 (10)	−0.0005 (8)	0.0103 (8)	−0.0008 (8)
C5	0.0285 (9)	0.0155 (10)	0.0227 (10)	0.0014 (7)	0.0141 (8)	0.0032 (7)
C6	0.0238 (9)	0.0163 (10)	0.0192 (9)	−0.0016 (7)	0.0132 (8)	−0.0018 (7)
C7	0.0239 (9)	0.0194 (10)	0.0181 (9)	−0.0020 (8)	0.0119 (8)	−0.0025 (8)
C8	0.0316 (10)	0.0233 (11)	0.0215 (10)	−0.0010 (8)	0.0117 (9)	−0.0021 (8)
C9	0.0246 (9)	0.0170 (10)	0.0243 (10)	−0.0003 (7)	0.0157 (8)	−0.0014 (8)
Ni1	0.0249 (2)	0.0112 (3)	0.0160 (3)	0.00245 (7)	0.00978 (19)	0.00329 (7)
O1	0.0346 (8)	0.0141 (7)	0.0212 (7)	−0.0010 (5)	0.0102 (6)	0.0009 (6)
O2	0.0520 (10)	0.0239 (9)	0.0193 (8)	0.0012 (7)	0.0070 (7)	0.0010 (7)
O3	0.0508 (10)	0.0231 (8)	0.0189 (8)	−0.0080 (7)	0.0111 (7)	−0.0034 (6)
O4	0.0761 (13)	0.0245 (9)	0.0189 (8)	−0.0031 (8)	0.0072 (8)	0.0062 (7)
O5	0.0348 (8)	0.0179 (8)	0.0331 (8)	−0.0015 (6)	0.0159 (7)	0.0024 (6)
O6	0.0358 (8)	0.0196 (7)	0.0222 (7)	−0.0037 (6)	0.0102 (6)	−0.0057 (6)
O1W	0.0583 (11)	0.0283 (8)	0.0682 (13)	0.0123 (9)	0.0489 (11)	0.0156 (9)
O2W	0.0453 (10)	0.0524 (11)	0.0384 (9)	0.0201 (9)	0.0289 (9)	0.0161 (9)
O3W	0.0399 (8)	0.0279 (9)	0.0331 (8)	−0.0027 (7)	0.0126 (7)	−0.0066 (7)

Geometric parameters (Å, º) top

C1—O2	1.236 (3)	C9—O5	1.244 (2)
C1—O1	1.273 (2)	C9—O6	1.266 (3)
C1—C2	1.500 (3)	Ni1—O6ⁱ	1.9129 (15)
C2—C7	1.386 (3)	Ni1—O1	1.9292 (14)
C2—C3	1.397 (3)	Ni1—O2W	1.9781 (17)
C3—C4	1.383 (3)	Ni1—O1W	1.9884 (18)
C3—H3	0.9300	Ni1—O3W	2.2536 (16)
C4—C5	1.394 (3)	O3—H3A	0.8200
C4—C8	1.480 (3)	O6—Ni1ⁱⁱ	1.9129 (15)
C5—C6	1.383 (3)	O1W—H1W	0.8501
C5—H5	0.9300	O1W—H2W	0.8500
C6—C7	1.400 (3)	O2W—H4W	0.8501
C6—C9	1.496 (3)	O2W—H3W	0.8500
C7—H7	0.9300	O3W—H5W	0.8501
C8—O4	1.210 (3)	O3W—H6W	0.8500
C8—O3	1.321 (3)

O2—C1—O1	123.25 (18)	O5—C9—C6	119.96 (17)
O2—C1—C2	121.17 (17)	O6—C9—C6	115.87 (16)
O1—C1—C2	115.58 (16)	O6ⁱ—Ni1—O1	174.25 (7)
C7—C2—C3	119.92 (18)	O6ⁱ—Ni1—O2W	93.67 (7)
C7—C2—C1	120.79 (17)	O1—Ni1—O2W	91.48 (7)
C3—C2—C1	119.28 (17)	O6ⁱ—Ni1—O1W	87.32 (7)
C4—C3—C2	120.44 (18)	O1—Ni1—O1W	88.13 (7)
C4—C3—H3	119.8	O2W—Ni1—O1W	168.69 (8)
C2—C3—H3	119.8	O6ⁱ—Ni1—O3W	90.27 (6)
C3—C4—C5	119.43 (18)	O1—Ni1—O3W	86.65 (6)
C3—C4—C8	121.08 (18)	O2W—Ni1—O3W	96.01 (8)
C5—C4—C8	119.48 (17)	O1W—Ni1—O3W	95.25 (8)
C6—C5—C4	120.64 (18)	C1—O1—Ni1	117.27 (12)
C6—C5—H5	119.7	C8—O3—H3A	109.5
C4—C5—H5	119.7	C9—O6—Ni1ⁱⁱ	120.96 (13)
C5—C6—C7	119.76 (18)	Ni1—O1W—H1W	99.8
C5—C6—C9	119.82 (18)	Ni1—O1W—H2W	105.1
C7—C6—C9	120.37 (16)	H1W—O1W—H2W	105.1
C2—C7—C6	119.80 (17)	Ni1—O2W—H4W	119.7
C2—C7—H7	120.1	Ni1—O2W—H3W	127.8
C6—C7—H7	120.1	H4W—O2W—H3W	105.1
O4—C8—O3	121.55 (19)	Ni1—O3W—H5W	121.4
O4—C8—C4	124.72 (19)	Ni1—O3W—H6W	108.0
O3—C8—C4	113.73 (18)	H5W—O3W—H6W	105.1
O5—C9—O6	124.16 (18)

O2—C1—C2—C7	4.9 (3)	C3—C4—C8—O4	169.1 (2)
O1—C1—C2—C7	−176.04 (17)	C5—C4—C8—O4	−9.6 (3)
O2—C1—C2—C3	−174.3 (2)	C3—C4—C8—O3	−10.9 (3)
O1—C1—C2—C3	4.8 (3)	C5—C4—C8—O3	170.43 (19)
C7—C2—C3—C4	0.2 (3)	C5—C6—C9—O5	−5.2 (3)
C1—C2—C3—C4	179.35 (17)	C7—C6—C9—O5	177.22 (18)
C2—C3—C4—C5	0.6 (3)	C5—C6—C9—O6	174.46 (18)
C2—C3—C4—C8	−178.15 (18)	C7—C6—C9—O6	−3.1 (3)
C3—C4—C5—C6	−0.6 (3)	O2—C1—O1—Ni1	−7.3 (3)
C8—C4—C5—C6	178.15 (19)	C2—C1—O1—Ni1	173.69 (13)
C4—C5—C6—C7	−0.1 (3)	O2W—Ni1—O1—C1	−72.99 (16)
C4—C5—C6—C9	−177.68 (17)	O1W—Ni1—O1—C1	95.70 (16)
C3—C2—C7—C6	−0.8 (3)	O3W—Ni1—O1—C1	−168.93 (15)
C1—C2—C7—C6	179.97 (17)	O5—C9—O6—Ni1ⁱⁱ	−6.8 (3)
C5—C6—C7—C2	0.8 (3)	C6—C9—O6—Ni1ⁱⁱ	173.52 (12)
C9—C6—C7—C2	178.38 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱⁱ	0.82	1.81	2.568 (2)	152
O1W—H1W···O3^iv	0.85	2.21	2.869 (3)	134
O1W—H2W···O5^v	0.85	1.94	2.680 (2)	145
O2W—H4W···O5^vi	0.85	1.89	2.715 (2)	165
O3W—H5W···O4^vii	0.85	2.03	2.778 (2)	147
O3W—H6W···O2^viii	0.85	2.49	3.068 (3)	126
O2W—H3W···O1^ix	0.85	2.34	3.123 (2)	154

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₄O₆)(H₂O)₃]
M_r	320.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.838 (2), 18.809 (5), 10.705 (3)
β (°)	126.901 (14)
V (Å³)	1101.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.81
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.613, 0.714
No. of measured, independent and observed [I > 2σ(I)] reflections	7973, 1938, 1864
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.102, 1.01
No. of reflections	1938
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.38

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O1	1.9292 (14)	Ni1—O3W	2.2536 (16)
Ni1—O2W	1.9781 (17)	O6—Ni1ⁱ	1.9129 (15)
Ni1—O1W	1.9884 (18)

Symmetry code: (i) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱ	0.82	1.81	2.568 (2)	152.3
O1W—H1W···O3ⁱⁱⁱ	0.85	2.21	2.869 (3)	133.9
O1W—H2W···O5^iv	0.85	1.94	2.680 (2)	145.0
O2W—H4W···O5^v	0.85	1.89	2.715 (2)	164.7
O3W—H5W···O4^vi	0.85	2.03	2.778 (2)	147.2
O3W—H6W···O2^vii	0.85	2.49	3.068 (3)	125.8
O2W—H3W···O1^viii	0.85	2.34	3.123 (2)	154.0

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

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