Tris(1,10-phenanthroline-κ2N,N′)nickel(II) bis­(2,4,5-tricarb­oxy­benzo­ate) monohydrate

Zhong, K.-L.; Ni, C.; Qian, M.-Y.

doi:10.1107/S1600536811048914

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1814-m1815

https://doi.org/10.1107/S1600536811048914

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Tris(1,10-phenanthroline-κ²N,N′)nickel(II) bis(2,4,5-tricarboxybenzoate) monohydrate

Kai-Long Zhong,^a ^* Chao Ni ^a and Ming-Yi Qian ^a

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: zklong76@163.com

(Received 11 November 2011; accepted 16 November 2011; online 23 November 2011)

In the title compound, [Ni(C₁₂H₈N₂)₃](C₁₀H₅O₈)₂·H₂O, the Ni^II cation is coordinated by six N atoms of the three bidentate chelating 1,10-phenanthroline ligands in a slightly distorted octahedral coordination geometry. The Ni—N bond lengths range from 2.074 (2) to 2.094 (2) Å. The dihedral angles between the three chelating NCCN groups to each other are 85.71 (3), 73.75 (2) and 85.71 (3)°, respectively. The Ni cation, the phenyl ring of the 1,10-phenanthroline ligand and the lattice water molecule are located on special positions (site symmetry 2). In the crystal, the uncoordinated 2,4,5-tricarboxybenzenoate anions join with each other through O—H⋯O hydrogen bonds, forming a two-dimensional hydrogen-bonded layer structure along the bc plane. The layers are further linked via additional O—H⋯O interactions between water and carboxyl groups, resulting in a three-dimensional supramolecular network.

Related literature

For structures of complexes with six-coordinate nickel atoms and background references, see: Li et al. (2003 ); Fu et al. (2004 ); Fabelo et al. (2008 ); Zhong et al. (2009 ); Ni et al. (2010 ). For background to phenanthroline complexes, see: Wang & Zhong (2011 ); Zhu et al. (2006 ); Cui et al. (2010 ); Zhong (2011a ,b ,c ).

Experimental

Crystal data

[Ni(C₁₂H₈N₂)₃](C₁₀H₅O₈)₂·H₂O
M_r = 1123.62
Monoclinic, C 2/c
a = 24.2009 (11) Å
b = 14.1546 (5) Å
c = 15.8347 (7) Å
β = 116.271 (5)°
V = 4864.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 295 K
0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). ABSPACK and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.829, T_max = 0.868
12270 measured reflections
4977 independent reflections
3050 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.054
S = 1.02
4977 reflections
369 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5ⁱ	0.82	1.87	2.690 (2)	177
O1—H5⋯O6ⁱⁱ	0.82	1.81	2.624 (2)	173
O7—H7⋯O6	0.82	1.63	2.4450 (19)	178
O1W—H1WA⋯O2ⁱⁱⁱ	0.80 (2)	2.10 (3)	2.866 (3)	158 (4)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). ABSPACK and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048914/bq2318sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048914/bq2318Isup2.hkl

checkCIF report

Comment top

1,10-Phenanthroline (Phen) and 1,2,4,5-Benzenetetracarboxylate have also been widely employed as polydentate ligands in coordination reactions and in the construction of supermolecular networks (Li et al., 2003; Fu et al., 2004; Fabelo et al., 2008). Recently we have synthesized and reported many metal-Phen complexes such as cadmium complexe (Zhong, 2011a), cobalt complexes (Wang & Zhong, 2011), copper complexes (Zhong 2011b,c), nickel complexes (Zhong et al., 2009; Ni et al., 2010), manganese complex (Zhu et al., 2006), and zinc complex (Cui et al., 2010). The title compound [Ni(C₁₂H₈N₂)₃](C₁₀H₅O₈)₂.H₂O, (I) was obtained unintentionally during an attempt to synthesize a mixed-ligand complex of Ni^II with Phen and 1,2,4,5-benzenetetracarboxylate ligand via a hydrothermal (solvothermal) reaction. The crystal structure of (I), has not hitherto been reported.

X-ray diffraction indicated that the title compound, (I), has the Ni²⁺ metal ion in a slightly distorted octahedral coordination geometry. The Ni^II atom is bonded by six N atoms of the three bidentate chelating 1,10-phenanthroline ligands. In the cation of [Ni(phen)₃]²⁺, the Ni—N bond distances range from 2.074 (2) Å to 2.094 (2) Å and the N—Ni—N bite angles [80.02 (7)–79.49 (9)°] (see Table 1), which are similar to the reported literature values (Zhong et al., 2009; Ni et al., 2010). The dihedral angles between the neighbor two chelating NCCN groups is 85.71 (3)°, 73.75 (2)° and 85.71 (3)°, respectively. A twofold rotation axis (symmetry code: -x + 2, y, -z + 3/2) passes through the Ni atom and the phenyl ring of 1,10-phenanthroline. In the crystal structure, the uncoordinated trihydrogen-1,2,4,5-benzenetetracarboxylate anions (C₁₀H₅O₈^-) connected to each other by intermolecular O—H···O H-bonds through carboxylic acid to form a two-dimensional hydrogen-bonded layer structure along bc plane. The adjacent layers are further linked via additional water O–H···O carboxyl hydrogen interactions, forming a three-dimensional supramolecular network structure.

Related literature top

For structures complexes with six-coordinate nickel atoms and background references, see: Li et al. (2003); Fu et al. (2004); Fabelo et al. (2008); Zhong et al. (2009); Ni et al. (2010). For background to phenanthroline complexes, see: Wang & Zhong (2011); Zhu et al. (2006); Cui et al. (2010); Zhong (2011a,b,c).

Experimental top

0.1 mmol NiSO₄^.7H₂O, 0.1 mmol phen, 0.1 mmol 1,2,4,5-Benzenetetracarboxylic acid and 3.0 ml water were mixed and placed in a thick Pyrex tube, which was sealed and heated to 423 K for 96 h, whereupon orange block-shaped crystals of (I) were obtained.

Structure description top

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The unit of (I), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 35% probability level. Unlabeled atoms of [Ni(C₁₂H₈N₂)₃]²⁺ and C₁₀H₅O₈^- anion are related to the labeled atoms by the symmetry operator -x + 2, y, -z + 3/2 and -x + 3/2, -y + 3/2, -z + 1, respectively.
	Fig. 2. Hydrogen-bonding interaction of (I), viewed along the a axis. Dashed lines indicate hydrogen bonds. All cations [Ni(C₁₂H₈N₂)₃]²⁺ and water molecules have been omitted for clarity.
	Fig. 3. The packing, viewed down the b axis. Dashed lines indicate hydrogen bonds. All cations [Ni(C₁₂H₈N₂)₃]²⁺ have been omitted for clarity.

Tris(1,10-phenanthroline-κ²N,N')nickel(II) bis(2,4,5-tricarboxybenzoate) monohydrate top

Crystal data top

[Ni(C₁₂H₈N₂)₃](C₁₀H₅O₈)₂·H₂O	F(000) = 2312
M_r = 1123.62	D_x = 1.534 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4069 reflections
a = 24.2009 (11) Å	θ = 2.8–29.2°
b = 14.1546 (5) Å	µ = 0.49 mm⁻¹
c = 15.8347 (7) Å	T = 295 K
β = 116.271 (5)°	Block, orange
V = 4864.0 (4) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	4977 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 15.9149 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −30→29
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009)	k = −14→17
T_min = 0.829, T_max = 0.868	l = −14→19
12270 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0092P)²] where P = (F_o² + 2F_c²)/3
4977 reflections	(Δ/σ)_max < 0.001
369 parameters	Δρ_max = 0.52 e Å⁻³
3 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ni(C₁₂H₈N₂)₃](C₁₀H₅O₈)₂·H₂O	V = 4864.0 (4) Å³
M_r = 1123.62	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.2009 (11) Å	µ = 0.49 mm⁻¹
b = 14.1546 (5) Å	T = 295 K
c = 15.8347 (7) Å	0.40 × 0.40 × 0.30 mm
β = 116.271 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	4977 independent reflections
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2009)	3050 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.868	R_int = 0.037
12270 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.52 e Å⁻³
4977 reflections	Δρ_min = −0.42 e Å⁻³
369 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
Ni1	1.0000	0.31042 (3)	0.7500	0.03040 (12)
N1	1.02407 (7)	0.21222 (12)	0.67422 (11)	0.0312 (5)
N2	0.91737 (7)	0.30145 (13)	0.62879 (11)	0.0326 (4)
N3	0.97131 (7)	0.42419 (13)	0.80545 (10)	0.0318 (5)
O1	0.68321 (7)	0.46426 (12)	0.52192 (11)	0.0511 (4)
H5	0.7152	0.4948	0.5473	0.077*
O1W	0.5000	0.5789 (3)	0.2500	0.1201 (14)
H1WA	0.4734 (13)	0.541 (2)	0.223 (3)	0.169 (19)*
O2	0.59675 (7)	0.46988 (12)	0.39080 (11)	0.0560 (5)
O3	0.70784 (6)	0.44147 (11)	0.35063 (10)	0.0452 (4)
O4	0.74751 (8)	0.53534 (11)	0.27810 (12)	0.0556 (5)
H4	0.7555	0.4850	0.2603	0.083*
O5	0.73100 (7)	0.86793 (11)	0.28224 (11)	0.0593 (5)
O6	0.71141 (6)	0.94807 (11)	0.38534 (10)	0.0459 (4)
O7	0.64163 (8)	0.93250 (12)	0.45856 (13)	0.0661 (5)
H7	0.6652	0.9388	0.4344	0.099*
O8	0.60196 (8)	0.81822 (13)	0.50512 (13)	0.0807 (6)
C1	1.07715 (9)	0.16650 (16)	0.69809 (14)	0.0398 (6)
H1	1.1077	0.1718	0.7597	0.048*
C2	1.08895 (10)	0.11114 (17)	0.63505 (17)	0.0456 (6)
H2	1.1267	0.0809	0.6543	0.055*
C3	1.04430 (10)	0.10193 (16)	0.54458 (17)	0.0424 (6)
H3	1.0517	0.0658	0.5016	0.051*
C4	0.98738 (9)	0.14703 (15)	0.51668 (15)	0.0344 (6)
C5	0.93748 (11)	0.13995 (16)	0.42380 (15)	0.0437 (6)
H9	0.9429	0.1063	0.3775	0.052*
C6	0.88307 (10)	0.18152 (17)	0.40309 (14)	0.0456 (6)
H8	0.8508	0.1735	0.3433	0.055*
C7	0.87341 (10)	0.23763 (16)	0.47020 (14)	0.0347 (6)
C8	0.81794 (10)	0.28303 (17)	0.45171 (15)	0.0481 (7)
H10	0.7846	0.2781	0.3925	0.058*
C9	0.81285 (10)	0.33462 (17)	0.52063 (17)	0.0483 (7)
H11	0.7759	0.3641	0.5093	0.058*
C10	0.86370 (10)	0.34262 (16)	0.60827 (15)	0.0416 (6)
H12	0.8598	0.3785	0.6545	0.050*
C11	0.92208 (9)	0.24801 (15)	0.56050 (14)	0.0284 (5)
C12	0.97938 (8)	0.20154 (15)	0.58436 (13)	0.0287 (5)
C13	0.94314 (9)	0.42376 (17)	0.86098 (14)	0.0423 (6)
H13	0.9339	0.3659	0.8795	0.051*
C14	0.92679 (10)	0.50594 (19)	0.89267 (17)	0.0535 (7)
H14	0.9068	0.5024	0.9311	0.064*
C15	0.94016 (10)	0.59170 (18)	0.86711 (16)	0.0543 (7)
H15	0.9296	0.6470	0.8882	0.065*
C16	0.97025 (9)	0.59569 (17)	0.80814 (15)	0.0383 (6)
C17	0.98481 (8)	0.50971 (16)	0.77988 (13)	0.0288 (5)
C18	0.98564 (9)	0.68215 (17)	0.77834 (14)	0.0504 (7)
H18	0.9760	0.7392	0.7978	0.061*
C19	0.66694 (8)	0.59686 (16)	0.41710 (14)	0.0303 (5)
C20	0.64826 (8)	0.67726 (16)	0.44598 (14)	0.0365 (6)
H20	0.6259	0.6701	0.4805	0.044*
C21	0.66067 (9)	0.76847 (16)	0.42678 (14)	0.0302 (5)
C22	0.69433 (8)	0.77913 (15)	0.37392 (13)	0.0273 (5)
C23	0.71376 (8)	0.69725 (17)	0.34589 (12)	0.0280 (5)
H23	0.7367	0.7037	0.3122	0.034*
C24	0.70075 (8)	0.60660 (16)	0.36553 (13)	0.0270 (5)
C25	0.71945 (9)	0.51885 (18)	0.33192 (14)	0.0325 (6)
C26	0.64675 (11)	0.50354 (17)	0.44011 (17)	0.0394 (6)
C27	0.63255 (10)	0.84283 (18)	0.46660 (17)	0.0454 (6)
C28	0.71315 (9)	0.87133 (16)	0.34430 (16)	0.0351 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0374 (2)	0.0251 (3)	0.0303 (2)	0.000	0.01641 (19)	0.000
N1	0.0359 (10)	0.0267 (13)	0.0322 (10)	0.0028 (9)	0.0161 (9)	0.0017 (9)
N2	0.0349 (10)	0.0291 (12)	0.0354 (10)	0.0031 (9)	0.0171 (9)	0.0028 (10)
N3	0.0416 (10)	0.0303 (13)	0.0327 (10)	−0.0019 (9)	0.0248 (9)	0.0017 (10)
O1	0.0665 (11)	0.0350 (12)	0.0542 (10)	−0.0138 (9)	0.0289 (10)	0.0063 (10)
O1W	0.112 (3)	0.062 (3)	0.127 (3)	0.000	−0.001 (3)	0.000
O2	0.0499 (10)	0.0400 (12)	0.0752 (12)	−0.0150 (9)	0.0251 (10)	0.0019 (11)
O3	0.0644 (10)	0.0244 (10)	0.0554 (10)	0.0035 (9)	0.0343 (9)	0.0033 (9)
O4	0.0908 (12)	0.0336 (11)	0.0732 (12)	0.0046 (10)	0.0643 (10)	−0.0030 (10)
O5	0.1064 (13)	0.0326 (11)	0.0727 (11)	−0.0077 (10)	0.0704 (11)	0.0013 (10)
O6	0.0653 (10)	0.0225 (9)	0.0604 (10)	−0.0061 (8)	0.0373 (9)	−0.0044 (9)
O7	0.0981 (14)	0.0290 (12)	0.1078 (15)	0.0010 (11)	0.0788 (12)	−0.0063 (12)
O8	0.1316 (15)	0.0434 (13)	0.1301 (16)	−0.0002 (12)	0.1151 (14)	−0.0050 (13)
C1	0.0394 (13)	0.0362 (17)	0.0406 (13)	0.0039 (12)	0.0147 (12)	−0.0007 (13)
C2	0.0487 (15)	0.0356 (17)	0.0616 (16)	0.0055 (13)	0.0327 (14)	−0.0006 (15)
C3	0.0641 (16)	0.0268 (15)	0.0555 (16)	−0.0045 (13)	0.0438 (15)	−0.0063 (14)
C4	0.0463 (14)	0.0269 (15)	0.0367 (13)	−0.0076 (11)	0.0246 (13)	−0.0005 (12)
C5	0.0723 (17)	0.0308 (16)	0.0377 (14)	−0.0149 (14)	0.0331 (15)	−0.0078 (13)
C6	0.0570 (15)	0.0426 (18)	0.0281 (12)	−0.0147 (14)	0.0106 (12)	−0.0014 (14)
C7	0.0457 (14)	0.0275 (15)	0.0303 (13)	−0.0064 (12)	0.0163 (12)	0.0056 (12)
C8	0.0427 (15)	0.046 (2)	0.0409 (14)	−0.0040 (13)	0.0051 (12)	0.0069 (14)
C9	0.0388 (14)	0.0433 (19)	0.0552 (15)	0.0050 (12)	0.0141 (14)	0.0066 (15)
C10	0.0451 (14)	0.0346 (17)	0.0469 (15)	0.0052 (12)	0.0220 (13)	0.0028 (13)
C11	0.0390 (13)	0.0206 (14)	0.0283 (12)	−0.0020 (10)	0.0175 (11)	0.0025 (11)
C12	0.0374 (12)	0.0224 (14)	0.0297 (12)	−0.0040 (11)	0.0180 (11)	0.0014 (11)
C13	0.0556 (14)	0.0351 (17)	0.0463 (14)	−0.0044 (13)	0.0318 (13)	0.0006 (14)
C14	0.0743 (17)	0.046 (2)	0.0668 (17)	0.0042 (15)	0.0549 (15)	−0.0026 (17)
C15	0.0809 (17)	0.0329 (17)	0.0708 (17)	0.0069 (15)	0.0533 (16)	−0.0060 (16)
C16	0.0501 (14)	0.0302 (16)	0.0444 (14)	0.0013 (12)	0.0298 (13)	−0.0029 (13)
C17	0.0332 (13)	0.0258 (14)	0.0302 (13)	−0.0002 (10)	0.0165 (11)	−0.0007 (12)
C18	0.0761 (17)	0.0225 (14)	0.0686 (18)	0.0042 (13)	0.0465 (14)	−0.0031 (15)
C19	0.0350 (12)	0.0241 (14)	0.0345 (13)	−0.0021 (11)	0.0177 (11)	−0.0004 (12)
C20	0.0473 (13)	0.0304 (16)	0.0461 (13)	−0.0033 (12)	0.0338 (12)	−0.0007 (14)
C21	0.0369 (12)	0.0248 (15)	0.0339 (12)	0.0003 (11)	0.0201 (11)	−0.0010 (12)
C22	0.0313 (12)	0.0238 (15)	0.0258 (12)	−0.0019 (10)	0.0117 (10)	0.0007 (11)
C23	0.0308 (11)	0.0329 (15)	0.0235 (11)	−0.0006 (11)	0.0149 (9)	−0.0003 (12)
C24	0.0332 (12)	0.0230 (14)	0.0256 (11)	0.0025 (10)	0.0136 (10)	−0.0012 (11)
C25	0.0355 (13)	0.0333 (16)	0.0285 (13)	0.0013 (12)	0.0140 (11)	−0.0007 (13)
C26	0.0517 (16)	0.0263 (16)	0.0506 (16)	0.0014 (13)	0.0320 (15)	−0.0006 (15)
C27	0.0636 (16)	0.0265 (16)	0.0581 (16)	0.0019 (13)	0.0380 (14)	−0.0019 (15)
C28	0.0419 (13)	0.0239 (14)	0.0392 (14)	0.0008 (11)	0.0176 (12)	0.0037 (11)

Geometric parameters (Å, º) top

Ni1—N2ⁱ	2.0740 (15)	C6—C7	1.426 (3)
Ni1—N2	2.0740 (15)	C6—H8	0.9300
Ni1—N1	2.0809 (16)	C7—C8	1.398 (3)
Ni1—N1ⁱ	2.0809 (16)	C7—C11	1.401 (2)
Ni1—N3ⁱ	2.0943 (17)	C8—C9	1.363 (3)
Ni1—N3	2.0943 (17)	C8—H10	0.9300
N1—C1	1.335 (2)	C9—C10	1.393 (3)
N1—C12	1.362 (2)	C9—H11	0.9300
N2—C10	1.326 (2)	C10—H12	0.9300
N2—C11	1.365 (2)	C11—C12	1.426 (2)
N3—C13	1.330 (2)	C13—C14	1.392 (3)
N3—C17	1.361 (2)	C13—H13	0.9300
O1—C26	1.324 (2)	C14—C15	1.363 (3)
O1—H5	0.8200	C14—H14	0.9300
O1W—H1WA	0.80 (2)	C15—C16	1.417 (3)
O2—C26	1.210 (2)	C15—H15	0.9300
O3—C25	1.200 (2)	C16—C17	1.395 (3)
O4—C25	1.324 (2)	C16—C18	1.419 (3)
O4—H4	0.8200	C17—C17ⁱ	1.433 (3)
O5—C28	1.237 (2)	C18—C18ⁱ	1.357 (3)
O6—C28	1.276 (2)	C18—H18	0.9300
O7—C27	1.304 (3)	C19—C20	1.375 (3)
O7—H7	0.8200	C19—C24	1.395 (2)
O8—C27	1.200 (2)	C19—C26	1.508 (3)
C1—C2	1.394 (3)	C20—C21	1.389 (3)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.366 (3)	C21—C22	1.411 (2)
C2—H2	0.9300	C21—C27	1.532 (3)
C3—C4	1.400 (3)	C22—C23	1.395 (3)
C3—H3	0.9300	C22—C28	1.523 (3)
C4—C12	1.402 (2)	C23—C24	1.389 (3)
C4—C5	1.435 (3)	C23—H23	0.9300
C5—C6	1.344 (3)	C24—C25	1.498 (3)
C5—H9	0.9300

N2ⁱ—Ni1—N2	172.98 (11)	C9—C10—H12	118.5
N2ⁱ—Ni1—N1	95.24 (6)	N2—C11—C7	122.64 (18)
N2—Ni1—N1	80.02 (7)	N2—C11—C12	117.26 (18)
N2ⁱ—Ni1—N1ⁱ	80.02 (7)	C7—C11—C12	120.10 (19)
N2—Ni1—N1ⁱ	95.24 (6)	N1—C12—C4	123.05 (18)
N1—Ni1—N1ⁱ	96.17 (9)	N1—C12—C11	117.05 (18)
N2ⁱ—Ni1—N3ⁱ	94.15 (6)	C4—C12—C11	119.90 (18)
N2—Ni1—N3ⁱ	91.25 (6)	N3—C13—C14	123.0 (2)
N1—Ni1—N3ⁱ	92.43 (6)	N3—C13—H13	118.5
N1ⁱ—Ni1—N3ⁱ	170.00 (7)	C14—C13—H13	118.5
N2ⁱ—Ni1—N3	91.25 (6)	C15—C14—C13	119.6 (2)
N2—Ni1—N3	94.15 (6)	C15—C14—H14	120.2
N1—Ni1—N3	170.00 (7)	C13—C14—H14	120.2
N1ⁱ—Ni1—N3	92.44 (6)	C14—C15—C16	119.3 (2)
N3ⁱ—Ni1—N3	79.49 (9)	C14—C15—H15	120.3
C1—N1—C12	117.49 (17)	C16—C15—H15	120.3
C1—N1—Ni1	129.83 (14)	C17—C16—C15	117.0 (2)
C12—N1—Ni1	112.40 (13)	C17—C16—C18	120.33 (19)
C10—N2—C11	117.75 (17)	C15—C16—C18	122.7 (2)
C10—N2—Ni1	129.68 (15)	N3—C17—C16	123.54 (18)
C11—N2—Ni1	112.50 (12)	N3—C17—C17ⁱ	117.22 (11)
C13—N3—C17	117.48 (19)	C16—C17—C17ⁱ	119.24 (13)
C13—N3—Ni1	129.48 (16)	C18ⁱ—C18—C16	120.44 (12)
C17—N3—Ni1	113.03 (12)	C18ⁱ—C18—H18	119.8
C26—O1—H5	109.5	C16—C18—H18	119.8
C25—O4—H4	109.5	C20—C19—C24	118.5 (2)
C27—O7—H7	109.5	C20—C19—C26	117.07 (18)
N1—C1—C2	123.10 (19)	C24—C19—C26	124.4 (2)
N1—C1—H1	118.5	C19—C20—C21	124.15 (19)
C2—C1—H1	118.5	C19—C20—H20	117.9
C3—C2—C1	119.1 (2)	C21—C20—H20	117.9
C3—C2—H2	120.4	C20—C21—C22	117.8 (2)
C1—C2—H2	120.4	C20—C21—C27	111.71 (17)
C2—C3—C4	119.9 (2)	C22—C21—C27	130.5 (2)
C2—C3—H3	120.1	C23—C22—C21	117.7 (2)
C4—C3—H3	120.1	C23—C22—C28	115.15 (18)
C3—C4—C12	117.33 (19)	C21—C22—C28	127.2 (2)
C3—C4—C5	123.7 (2)	C24—C23—C22	123.67 (17)
C12—C4—C5	118.92 (19)	C24—C23—H23	118.2
C6—C5—C4	120.6 (2)	C22—C23—H23	118.2
C6—C5—H9	119.7	C23—C24—C19	118.2 (2)
C4—C5—H9	119.7	C23—C24—C25	123.52 (19)
C5—C6—C7	121.9 (2)	C19—C24—C25	118.3 (2)
C5—C6—H8	119.1	O3—C25—O4	124.2 (2)
C7—C6—H8	119.1	O3—C25—C24	121.9 (2)
C8—C7—C11	117.5 (2)	O4—C25—C24	113.8 (2)
C8—C7—C6	124.0 (2)	O2—C26—O1	120.6 (2)
C11—C7—C6	118.55 (19)	O2—C26—C19	121.8 (2)
C9—C8—C7	119.8 (2)	O1—C26—C19	117.2 (2)
C9—C8—H10	120.1	O8—C27—O7	120.0 (2)
C7—C8—H10	120.1	O8—C27—C21	119.7 (2)
C8—C9—C10	119.2 (2)	O7—C27—C21	120.2 (2)
C8—C9—H11	120.4	O5—C28—O6	122.7 (2)
C10—C9—H11	120.4	O5—C28—C22	117.9 (2)
N2—C10—C9	123.1 (2)	O6—C28—C22	119.40 (19)
N2—C10—H12	118.5

N2ⁱ—Ni1—N1—C1	−3.79 (18)	Ni1—N1—C12—C11	−7.6 (2)
N2—Ni1—N1—C1	−178.55 (18)	C3—C4—C12—N1	0.2 (3)
N1ⁱ—Ni1—N1—C1	−84.29 (18)	C5—C4—C12—N1	179.90 (19)
N3ⁱ—Ni1—N1—C1	90.60 (18)	C3—C4—C12—C11	−179.05 (18)
N3—Ni1—N1—C1	126.5 (4)	C5—C4—C12—C11	0.6 (3)
N2ⁱ—Ni1—N1—C12	−177.45 (13)	N2—C11—C12—N1	1.8 (3)
N2—Ni1—N1—C12	7.79 (13)	C7—C11—C12—N1	−177.96 (19)
N1ⁱ—Ni1—N1—C12	102.05 (14)	N2—C11—C12—C4	−178.87 (17)
N3ⁱ—Ni1—N1—C12	−83.05 (13)	C7—C11—C12—C4	1.3 (3)
N3—Ni1—N1—C12	−47.1 (4)	C17—N3—C13—C14	0.6 (3)
N2ⁱ—Ni1—N2—C10	128.53 (18)	Ni1—N3—C13—C14	179.91 (17)
N1—Ni1—N2—C10	176.55 (19)	N3—C13—C14—C15	−0.5 (4)
N1ⁱ—Ni1—N2—C10	81.19 (18)	C13—C14—C15—C16	0.4 (4)
N3ⁱ—Ni1—N2—C10	−91.19 (18)	C14—C15—C16—C17	−0.3 (3)
N3—Ni1—N2—C10	−11.64 (19)	C14—C15—C16—C18	179.9 (2)
N2ⁱ—Ni1—N2—C11	−54.87 (13)	C13—N3—C17—C16	−0.5 (3)
N1—Ni1—N2—C11	−6.84 (13)	Ni1—N3—C17—C16	180.00 (16)
N1ⁱ—Ni1—N2—C11	−102.20 (13)	C13—N3—C17—C17ⁱ	179.96 (18)
N3ⁱ—Ni1—N2—C11	85.41 (14)	Ni1—N3—C17—C17ⁱ	0.5 (3)
N3—Ni1—N2—C11	164.96 (13)	C15—C16—C17—N3	0.4 (3)
N2ⁱ—Ni1—N3—C13	−85.57 (16)	C18—C16—C17—N3	−179.79 (19)
N2—Ni1—N3—C13	89.94 (16)	C15—C16—C17—C17ⁱ	179.9 (2)
N1—Ni1—N3—C13	143.9 (3)	C18—C16—C17—C17ⁱ	−0.3 (4)
N1ⁱ—Ni1—N3—C13	−5.50 (16)	C17—C16—C18—C18ⁱ	0.4 (4)
N3ⁱ—Ni1—N3—C13	−179.55 (19)	C15—C16—C18—C18ⁱ	−179.9 (2)
N2ⁱ—Ni1—N3—C17	93.81 (14)	C24—C19—C20—C21	0.3 (3)
N2—Ni1—N3—C17	−90.68 (14)	C26—C19—C20—C21	−177.1 (2)
N1—Ni1—N3—C17	−36.8 (4)	C19—C20—C21—C22	0.3 (3)
N1ⁱ—Ni1—N3—C17	173.87 (14)	C19—C20—C21—C27	178.78 (19)
N3ⁱ—Ni1—N3—C17	−0.18 (10)	C20—C21—C22—C23	−1.1 (3)
C12—N1—C1—C2	1.6 (3)	C27—C21—C22—C23	−179.2 (2)
Ni1—N1—C1—C2	−171.78 (16)	C20—C21—C22—C28	179.9 (2)
N1—C1—C2—C3	−0.6 (3)	C27—C21—C22—C28	1.7 (3)
C1—C2—C3—C4	−0.7 (3)	C21—C22—C23—C24	1.3 (3)
C2—C3—C4—C12	0.8 (3)	C28—C22—C23—C24	−179.49 (18)
C2—C3—C4—C5	−178.8 (2)	C22—C23—C24—C19	−0.8 (3)
C3—C4—C5—C6	176.8 (2)	C22—C23—C24—C25	177.38 (18)
C12—C4—C5—C6	−2.8 (3)	C20—C19—C24—C23	−0.1 (3)
C4—C5—C6—C7	3.0 (3)	C26—C19—C24—C23	177.1 (2)
C5—C6—C7—C8	179.3 (2)	C20—C19—C24—C25	−178.30 (19)
C5—C6—C7—C11	−1.0 (3)	C26—C19—C24—C25	−1.2 (3)
C11—C7—C8—C9	−0.2 (3)	C23—C24—C25—O3	179.5 (2)
C6—C7—C8—C9	179.5 (2)	C19—C24—C25—O3	−2.4 (3)
C7—C8—C9—C10	1.2 (3)	C23—C24—C25—O4	−2.7 (3)
C11—N2—C10—C9	−0.8 (3)	C19—C24—C25—O4	175.48 (17)
Ni1—N2—C10—C9	175.62 (17)	C20—C19—C26—O2	83.8 (3)
C8—C9—C10—N2	−0.6 (3)	C24—C19—C26—O2	−93.4 (3)
C10—N2—C11—C7	1.8 (3)	C20—C19—C26—O1	−89.2 (2)
Ni1—N2—C11—C7	−175.25 (16)	C24—C19—C26—O1	93.6 (2)
C10—N2—C11—C12	−177.99 (18)	C20—C21—C27—O8	−2.9 (3)
Ni1—N2—C11—C12	5.0 (2)	C22—C21—C27—O8	175.3 (2)
C8—C7—C11—N2	−1.3 (3)	C20—C21—C27—O7	177.2 (2)
C6—C7—C11—N2	179.00 (18)	C22—C21—C27—O7	−4.5 (4)
C8—C7—C11—C12	178.51 (18)	C23—C22—C28—O5	15.8 (3)
C6—C7—C11—C12	−1.2 (3)	C21—C22—C28—O5	−165.12 (18)
C1—N1—C12—C4	−1.4 (3)	C23—C22—C28—O6	−162.56 (18)
Ni1—N1—C12—C4	173.10 (15)	C21—C22—C28—O6	16.5 (3)
C1—N1—C12—C11	177.87 (17)

Symmetry code: (i) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱⁱ	0.82	1.87	2.690 (2)	177
O1—H5···O6ⁱⁱⁱ	0.82	1.81	2.624 (2)	173
O7—H7···O6	0.82	1.63	2.4450 (19)	178
O1W—H1WA···O2^iv	0.80 (2)	2.10 (3)	2.866 (3)	158 (4)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₈N₂)₃](C₁₀H₅O₈)₂·H₂O
M_r	1123.62
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	24.2009 (11), 14.1546 (5), 15.8347 (7)
β (°)	116.271 (5)
V (Å³)	4864.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini ultra
Absorption correction	Multi-scan (ABSPACK; Oxford Diffraction, 2009)
T_min, T_max	0.829, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	12270, 4977, 3050
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.054, 1.02
No. of reflections	4977
No. of parameters	369
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.42

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱ	0.82	1.87	2.690 (2)	176.7
O1—H5···O6ⁱⁱ	0.82	1.81	2.624 (2)	173.1
O7—H7···O6	0.82	1.63	2.4450 (19)	178.3
O1W—H1WA···O2ⁱⁱⁱ	0.80 (2)	2.10 (3)	2.866 (3)	158 (4)

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

Acknowledgements

This work was supported by the Scientific Research Foundation of Nanjing College of Chemical Technology (grant No. NHKY-2010–17).

References

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