catena-Poly[[tetra­aqua­nickel(II)]-μ-(9,10-dioxo-9,10-dihydro­anthracene-1,4,5,8-tetra­carboxyl­ato)-κ2O1:O8-[tetra­aqua­nickel(II)]-μ-4,4′-bipyridine-κ2N:N′]

Liu, Y.-M.; Cao, K.; Wang, F.-L.

doi:10.1107/S1600536812027493

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m960-m961

https://doi.org/10.1107/S1600536812027493

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catena-Poly[[tetraaquanickel(II)]-μ-(9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylato)-κ²O¹:O⁸-[tetraaquanickel(II)]-μ-4,4′-bipyridine-κ²N:N′]

Yang-Mei Liu,^a,^b Kai Cao ^a ^* and Feng-Lin Wang ^a

^aNational Food Packaging Products Quality Supervision and Inspection Center, Jiangsu Provincial Supervising and Testing Research Institute for Products Quality, Nanjing 210007, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hare1014@163.com

(Received 8 June 2012; accepted 18 June 2012; online 23 June 2012)

In the crystal of the title polymeric complex, [Ni₂(C₁₈H₄O₁₀)(C₁₀H₈N₂)(H₂O)₈]_n, each Ni^II cation is coordinated by four water molecules in the equatorial plane, and is further bridged by an 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylate anion and a 4,4′-bipyridine ligand in the axial directions, forming a distorted octahedral geometry. The 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylate anion is centrosymmetric with the centroid of the quinone ring located about an inversion center; the 4,4′-bipyridine ligand is also centrosymmetric with the mid-point of the C—C bond linking two pyridine rings located about another invertion center. The 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylate anion and bypiridine ligand bridge the Ni^II cations, forming a polymeric chain along the b axis. π–π stacking is observed between pyridine and benzene rings [centroid–centroid distance = 3.705 (2) Å]. All of the coordinating water molecules are involved in O—H⋯O hydrogen bonding.

Related literature

For the synthesis, see: Liu et al. (2010 ).

Experimental

Crystal data

[Ni₂(C₁₈H₄O₁₀)(C₁₀H₈N₂)(H₂O)₈]
M_r = 797.94
Monoclinic, P 2₁ /n
a = 8.6359 (16) Å
b = 21.2426 (12) Å
c = 8.6416 (13) Å
β = 92.789 (3)°
V = 1583.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 291 K
0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.716, T_max = 0.767
8595 measured reflections
3111 independent reflections
2297 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.102
S = 1.00
3111 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6X⋯O4	0.85	2.14	2.642 (4)	118
O6—H6Y⋯O1ⁱ	0.85	2.16	2.630 (3)	115
O7—H7Y⋯O2ⁱ	0.85	1.82	2.618 (3)	155
O7—H7X⋯O4ⁱⁱ	0.85	1.88	2.717 (4)	168
O8—H8X⋯O6ⁱⁱ	0.85	2.42	3.243 (4)	164
O8—H8Y⋯O7ⁱⁱⁱ	0.85	2.50	3.330 (4)	167
O9—H9X⋯O7ⁱⁱⁱ	0.85	2.17	2.973 (3)	158
O9—H9Y⋯O3	0.85	2.26	3.099 (3)	170
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 I, global. DOI: https://doi.org/10.1107/S1600536812027493/xu5560sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027493/xu5560Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title complex (I) is showing in Fig. 1. The asymmetric unit of I contains one independent nickel(II) ion, a half 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylic acid ligand, a half 4,4-bipyridine ligand, four coordinating water molecules.

The nickel atom is in a normal octahedral geometry with O atoms which from the coordinating water molecules on the equatorial plane and O atom from the carboxylate group, N atom from the 4,4-bipyridine in the axial position. Every nickel atom is coordinated with one 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylate ligand and one 4,4-bipyridine ligand. And every 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylic acid ligand coordinates with two nickel atoms and they form a one-dimensional nickel chain along b axis. There are two nickel chains which cross each other in the crystal structure.

Related literature top

For the synthesis, see: Liu et al. (2010).

Experimental top

The title compound was obtained unintentionally as the product of an attempted synthesis of a polymeric network Ni complex with 9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylic acid and 4,4-bipyridine (Liu et al., 2010), the pH value of the mixture was adjusted to 8.0 with NaOH solution, and then solution was heated at 393 K for 3 d. After the mixture was slowly cooled to room temperature, green crystals of the title compound were obtained.

Structure description top

For the synthesis, see: Liu et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of (I), viewed down the a axis.

catena-Poly[[tetraaquanickel(II)]- µ-(9,10-dioxo-9,10-dihydroanthracene-1,4,5,8-tetracarboxylato)- κ²O¹:O⁸-[tetraaquanickel(II)]- µ-4,4'-bipyridine-κ²N:N'] top

Crystal data top

[Ni₂(C₁₈H₄O₁₀)(C₁₀H₈N₂)(H₂O)₈]	F(000) = 820
M_r = 797.94	D_x = 1.674 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1207 reflections
a = 8.6359 (16) Å	θ = 2.5–21.8°
b = 21.2426 (12) Å	µ = 1.28 mm⁻¹
c = 8.6416 (13) Å	T = 291 K
β = 92.789 (3)°	Block, green
V = 1583.4 (4) Å³	0.28 × 0.24 × 0.22 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD diffractometer	3111 independent reflections
Radiation source: sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
T_min = 0.716, T_max = 0.767	k = −26→25
8595 measured reflections	l = −7→10

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.04P)² + 1.66P] where P = (F_o² + 2F_c²)/3
3111 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Ni₂(C₁₈H₄O₁₀)(C₁₀H₈N₂)(H₂O)₈]	V = 1583.4 (4) Å³
M_r = 797.94	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6359 (16) Å	µ = 1.28 mm⁻¹
b = 21.2426 (12) Å	T = 291 K
c = 8.6416 (13) Å	0.28 × 0.24 × 0.22 mm
β = 92.789 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3111 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2297 reflections with I > 2σ(I)
T_min = 0.716, T_max = 0.767	R_int = 0.056
8595 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.86 e Å⁻³
3111 reflections	Δρ_min = −0.49 e Å⁻³
226 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	0.1039 (5)	0.38729 (17)	0.6495 (5)	0.0279 (9)
C2	0.2016 (4)	0.39108 (17)	0.7843 (4)	0.0231 (8)
H2	0.2351	0.3543	0.8334	0.028*
C3	0.2482 (4)	0.44891 (17)	0.8487 (4)	0.0219 (8)
H3	0.3128	0.4499	0.9380	0.026*
C4	0.1983 (5)	0.50468 (18)	0.7798 (4)	0.0253 (8)
C5	0.1014 (4)	0.50163 (17)	0.6407 (4)	0.0197 (7)
C6	0.0513 (4)	0.44257 (18)	0.5757 (4)	0.0243 (8)
C7	−0.0636 (4)	0.43979 (16)	0.4486 (4)	0.0177 (7)
C8	0.2460 (5)	0.56481 (18)	0.8562 (4)	0.0254 (8)
C9	0.0736 (4)	0.32135 (17)	0.5866 (4)	0.0225 (8)
C10	0.0110 (4)	0.14286 (18)	0.0564 (4)	0.0228 (8)
H10	−0.0205	0.1805	0.0100	0.027*
C11	−0.0207 (4)	0.08759 (16)	−0.0196 (4)	0.0222 (8)
H11	−0.0731	0.0895	−0.1161	0.027*
C12	0.0200 (4)	0.02965 (17)	0.0378 (4)	0.0223 (8)
C13	0.1022 (4)	0.03075 (17)	0.1803 (4)	0.0226 (8)
H13	0.1327	−0.0067	0.2285	0.027*
C14	0.1388 (5)	0.08895 (17)	0.2511 (4)	0.0265 (8)
H14	0.2024	0.0894	0.3411	0.032*
N1	0.0841 (3)	0.14441 (14)	0.1922 (4)	0.0229 (7)
Ni1	0.10940 (5)	0.22477 (2)	0.33004 (5)	0.02030 (14)
O1	0.3792 (3)	0.57569 (12)	0.8713 (3)	0.0307 (7)
O2	0.1359 (3)	0.59770 (12)	0.9128 (3)	0.0290 (6)
O3	−0.1319 (3)	0.39084 (11)	0.4195 (3)	0.0222 (6)
O4	0.0032 (3)	0.28515 (12)	0.6693 (3)	0.0293 (6)
O5	0.1290 (3)	0.30879 (11)	0.4574 (3)	0.0242 (6)
O6	0.0040 (3)	0.17982 (11)	0.5068 (3)	0.0214 (5)
H6X	0.0512	0.1923	0.5898	0.026*
H6Y	−0.0052	0.1415	0.4795	0.026*
O7	0.3310 (3)	0.20054 (11)	0.4219 (3)	0.0204 (5)
H7X	0.3965	0.2055	0.3525	0.024*
H7Y	0.3314	0.1623	0.4510	0.024*
O8	0.1681 (3)	0.27455 (12)	0.1160 (3)	0.0289 (6)
H8X	0.2466	0.2873	0.0692	0.035*
H8Y	0.0907	0.2797	0.0526	0.035*
O9	−0.1130 (3)	0.26235 (12)	0.2516 (3)	0.0269 (6)
H9X	−0.1200	0.2630	0.1531	0.032*
H9Y	−0.1223	0.2996	0.2861	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (2)	0.0167 (19)	0.029 (2)	−0.0067 (17)	0.0048 (17)	0.0011 (16)
C2	0.030 (2)	0.0183 (18)	0.0221 (19)	0.0004 (15)	0.0091 (15)	0.0003 (14)
C3	0.0259 (19)	0.0222 (19)	0.0173 (18)	−0.0010 (15)	−0.0017 (14)	−0.0068 (14)
C4	0.032 (2)	0.0183 (18)	0.026 (2)	−0.0035 (16)	0.0039 (16)	−0.0004 (15)
C5	0.0205 (18)	0.0158 (17)	0.0234 (19)	0.0034 (14)	0.0068 (14)	−0.0014 (14)
C6	0.0250 (19)	0.028 (2)	0.0190 (19)	0.0009 (16)	−0.0060 (15)	−0.0030 (15)
C7	0.0182 (16)	0.0215 (19)	0.0129 (17)	−0.0045 (14)	−0.0039 (13)	−0.0033 (13)
C8	0.032 (2)	0.027 (2)	0.0173 (18)	−0.0026 (17)	−0.0018 (15)	−0.0035 (15)
C9	0.0210 (18)	0.0227 (19)	0.025 (2)	0.0110 (15)	0.0092 (15)	0.0008 (15)
C10	0.034 (2)	0.0190 (18)	0.0156 (18)	0.0016 (16)	0.0027 (15)	−0.0020 (14)
C11	0.034 (2)	0.0181 (18)	0.0145 (18)	−0.0110 (16)	−0.0041 (14)	−0.0021 (14)
C12	0.0266 (19)	0.0186 (19)	0.0213 (19)	−0.0064 (15)	−0.0029 (14)	−0.0054 (15)
C13	0.0229 (19)	0.0194 (18)	0.026 (2)	0.0073 (15)	0.0082 (15)	0.0004 (15)
C14	0.034 (2)	0.0195 (19)	0.025 (2)	−0.0061 (16)	−0.0079 (16)	0.0010 (15)
N1	0.0224 (15)	0.0182 (15)	0.0271 (17)	0.0018 (13)	−0.0096 (13)	−0.0073 (13)
Ni1	0.0171 (2)	0.0217 (2)	0.0218 (2)	0.0006 (2)	−0.00221 (16)	−0.0025 (2)
O1	0.0302 (16)	0.0160 (13)	0.0459 (18)	−0.0110 (12)	0.0011 (13)	−0.0077 (12)
O2	0.0299 (15)	0.0217 (14)	0.0342 (16)	0.0048 (11)	−0.0101 (12)	−0.0123 (11)
O3	0.0311 (14)	0.0136 (13)	0.0200 (13)	0.0032 (10)	−0.0177 (11)	−0.0030 (10)
O4	0.0465 (17)	0.0224 (14)	0.0193 (13)	−0.0118 (12)	0.0035 (12)	−0.0132 (11)
O5	0.0356 (15)	0.0155 (13)	0.0219 (13)	0.0004 (11)	0.0049 (11)	0.0015 (10)
O6	0.0235 (13)	0.0210 (13)	0.0193 (13)	0.0063 (11)	−0.0032 (10)	0.0017 (10)
O7	0.0194 (12)	0.0205 (13)	0.0206 (13)	−0.0057 (10)	−0.0064 (10)	0.0019 (10)
O8	0.0405 (16)	0.0186 (13)	0.0279 (15)	−0.0069 (12)	0.0047 (12)	0.0000 (11)
O9	0.0299 (14)	0.0215 (14)	0.0286 (14)	0.0075 (11)	−0.0054 (11)	0.0006 (11)

Geometric parameters (Å, º) top

C1—C6	1.401 (5)	C11—H11	0.9300
C1—C2	1.407 (6)	C12—C13	1.391 (5)
C1—C9	1.521 (5)	C12—C12ⁱⁱ	1.453 (7)
C2—C3	1.400 (5)	C13—C14	1.409 (5)
C2—H2	0.9298	C13—H13	0.9300
C3—C4	1.385 (5)	C14—N1	1.359 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.432 (5)	N1—Ni1	2.087 (3)
C4—C8	1.487 (5)	Ni1—O6	2.051 (2)
C5—C6	1.433 (5)	Ni1—O5	2.099 (3)
C5—C7ⁱ	1.492 (5)	Ni1—O7	2.100 (2)
C6—C7	1.445 (5)	Ni1—O9	2.159 (3)
C7—O3	1.215 (4)	Ni1—O8	2.211 (3)
C7—C5ⁱ	1.492 (5)	O6—H6X	0.8500
C8—O1	1.174 (5)	O6—H6Y	0.8500
C8—O2	1.295 (5)	O7—H7X	0.8500
C9—O4	1.230 (4)	O7—H7Y	0.8500
C9—O5	1.265 (4)	O8—H8X	0.8505
C10—N1	1.305 (5)	O8—H8Y	0.8498
C10—C11	1.366 (5)	O9—H9X	0.8500
C10—H10	0.9300	O9—H9Y	0.8499
C11—C12	1.367 (5)

C6—C1—C2	119.8 (3)	C12—C13—H13	120.2
C6—C1—C9	124.3 (4)	C14—C13—H13	120.2
C2—C1—C9	115.7 (3)	N1—C14—C13	122.1 (3)
C3—C2—C1	121.9 (3)	N1—C14—H14	119.0
C3—C2—H2	118.6	C13—C14—H14	119.0
C1—C2—H2	119.4	C10—N1—C14	117.3 (3)
C4—C3—C2	120.1 (3)	C10—N1—Ni1	124.5 (3)
C4—C3—H3	119.9	C14—N1—Ni1	118.0 (2)
C2—C3—H3	119.9	O6—Ni1—N1	90.37 (12)
C3—C4—C5	118.6 (3)	O6—Ni1—O5	91.88 (10)
C3—C4—C8	118.0 (3)	N1—Ni1—O5	176.51 (11)
C5—C4—C8	123.3 (3)	O6—Ni1—O7	91.93 (10)
C4—C5—C6	121.4 (3)	N1—Ni1—O7	94.80 (10)
C4—C5—C7ⁱ	120.0 (3)	O5—Ni1—O7	87.80 (10)
C6—C5—C7ⁱ	118.3 (3)	O6—Ni1—O9	89.18 (10)
C1—C6—C5	118.1 (3)	N1—Ni1—O9	93.22 (11)
C1—C6—C7	120.5 (3)	O5—Ni1—O9	84.14 (10)
C5—C6—C7	121.1 (3)	O7—Ni1—O9	171.90 (10)
O3—C7—C6	120.0 (3)	O6—Ni1—O8	166.82 (10)
O3—C7—C5ⁱ	121.0 (3)	N1—Ni1—O8	86.30 (11)
C6—C7—C5ⁱ	118.9 (3)	O5—Ni1—O8	90.92 (9)
O1—C8—O2	125.8 (4)	O7—Ni1—O8	101.05 (10)
O1—C8—C4	117.9 (4)	O9—Ni1—O8	78.29 (11)
O2—C8—C4	116.0 (3)	C9—O5—Ni1	128.2 (2)
O4—C9—O5	126.9 (4)	Ni1—O6—H6X	105.7
O4—C9—C1	116.7 (3)	Ni1—O6—H6Y	106.1
O5—C9—C1	116.3 (3)	H6X—O6—H6Y	124.6
N1—C10—C11	122.0 (4)	Ni1—O7—H7X	109.2
N1—C10—H10	119.0	Ni1—O7—H7Y	109.6
C11—C10—H10	119.0	H7X—O7—H7Y	109.5
C10—C11—C12	123.9 (3)	Ni1—O8—H8X	140.4
C10—C11—H11	118.1	Ni1—O8—H8Y	113.3
C12—C11—H11	118.1	H8X—O8—H8Y	105.8
C11—C12—C13	114.7 (3)	Ni1—O9—H9X	109.8
C11—C12—C12ⁱⁱ	124.5 (4)	Ni1—O9—H9Y	109.3
C13—C12—C12ⁱⁱ	120.8 (4)	H9X—O9—H9Y	109.5
C12—C13—C14	119.6 (3)

C6—C1—C2—C3	0.3 (6)	C2—C1—C9—O4	64.4 (5)
C9—C1—C2—C3	175.5 (3)	C6—C1—C9—O5	62.1 (5)
C1—C2—C3—C4	0.0 (6)	C2—C1—C9—O5	−112.8 (4)
C2—C3—C4—C5	−1.2 (6)	N1—C10—C11—C12	0.1 (6)
C2—C3—C4—C8	177.6 (4)	C10—C11—C12—C13	−1.9 (6)
C3—C4—C5—C6	2.3 (5)	C10—C11—C12—C12ⁱⁱ	176.5 (5)
C8—C4—C5—C6	−176.5 (4)	C11—C12—C13—C14	−1.2 (5)
C3—C4—C5—C7ⁱ	−171.5 (3)	C12ⁱⁱ—C12—C13—C14	−179.7 (4)
C8—C4—C5—C7ⁱ	9.7 (6)	C12—C13—C14—N1	6.3 (6)
C2—C1—C6—C5	0.7 (6)	C11—C10—N1—C14	4.9 (6)
C9—C1—C6—C5	−174.0 (3)	C11—C10—N1—Ni1	−170.8 (3)
C2—C1—C6—C7	−172.5 (3)	C13—C14—N1—C10	−8.1 (6)
C9—C1—C6—C7	12.8 (6)	C13—C14—N1—Ni1	167.9 (3)
C4—C5—C6—C1	−2.0 (6)	C10—N1—Ni1—O6	122.4 (3)
C7ⁱ—C5—C6—C1	171.9 (3)	C14—N1—Ni1—O6	−53.4 (3)
C4—C5—C6—C7	171.1 (3)	C10—N1—Ni1—O7	−145.7 (3)
C7ⁱ—C5—C6—C7	−15.0 (6)	C14—N1—Ni1—O7	38.6 (3)
C1—C6—C7—O3	10.8 (6)	C10—N1—Ni1—O9	33.2 (3)
C5—C6—C7—O3	−162.2 (3)	C14—N1—Ni1—O9	−142.6 (3)
C1—C6—C7—C5ⁱ	−171.9 (3)	C10—N1—Ni1—O8	−44.9 (3)
C5—C6—C7—C5ⁱ	15.1 (6)	C14—N1—Ni1—O8	139.4 (3)
C3—C4—C8—O1	60.7 (5)	O4—C9—O5—Ni1	4.4 (6)
C5—C4—C8—O1	−120.5 (4)	C1—C9—O5—Ni1	−178.6 (2)
C3—C4—C8—O2	−113.1 (4)	O6—Ni1—O5—C9	−6.8 (3)
C5—C4—C8—O2	65.7 (5)	O9—Ni1—O5—C9	82.2 (3)
C6—C1—C9—O4	−120.6 (4)	O8—Ni1—O5—C9	160.3 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6X···O4	0.85	2.14	2.642 (4)	118
O6—H6Y···O1ⁱⁱⁱ	0.85	2.16	2.630 (3)	115
O7—H7Y···O2ⁱⁱⁱ	0.85	1.82	2.618 (3)	155
O7—H7X···O4^iv	0.85	1.88	2.717 (4)	168
O8—H8X···O6^iv	0.85	2.42	3.243 (4)	164
O8—H8Y···O7^v	0.85	2.50	3.330 (4)	167
O9—H9X···O7^v	0.85	2.17	2.973 (3)	158
O9—H9Y···O3	0.85	2.26	3.099 (3)	170

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

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₈H₄O₁₀)(C₁₀H₈N₂)(H₂O)₈]
M_r	797.94
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	8.6359 (16), 21.2426 (12), 8.6416 (13)
β (°)	92.789 (3)
V (Å³)	1583.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.716, 0.767
No. of measured, independent and observed [I > 2σ(I)] reflections	8595, 3111, 2297
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.102, 1.00
No. of reflections	3111
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.49

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6X···O4	0.85	2.14	2.642 (4)	118
O6—H6Y···O1ⁱ	0.85	2.16	2.630 (3)	115
O7—H7Y···O2ⁱ	0.85	1.82	2.618 (3)	155
O7—H7X···O4ⁱⁱ	0.85	1.88	2.717 (4)	168
O8—H8X···O6ⁱⁱ	0.85	2.42	3.243 (4)	164
O8—H8Y···O7ⁱⁱⁱ	0.85	2.50	3.330 (4)	167
O9—H9X···O7ⁱⁱⁱ	0.85	2.17	2.973 (3)	158
O9—H9Y···O3	0.85	2.26	3.099 (3)	170

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

Acknowledgements

This work was supported financially by the Science and Technology Project of the State General Administration of Quality Supervision, Inspection and Quarantine, China (2011QK121, 2011QK122).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, Y.-M., He, R., Wang, F.-M., Lu, C.-S. & Meng, Q.-J. (2010). Inorg. Chem. Commun. 13, 1375–1379. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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