Poly[aqua­[μ-1,2-bis­(pyridin-4-yl)ethene-κ2N:N′][μ-5-(diphenyl­phosphino­yl)iso­phthalato-κ3O1,O1′:O3]nickel(II)]

Zhang, P.; Liu, Y.-J.; Li, K.-H.; Yang, G.-R.; Mei, C.-Z.

doi:10.1107/S1600536812031108

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages m1058-m1059

https://doi.org/10.1107/S1600536812031108

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Poly[aqua[μ-1,2-bis(pyridin-4-yl)ethene-κ²N:N′][μ-5-(diphenylphosphinoyl)isophthalato-κ³O¹,O^1′:O³]nickel(II)]

Peng Zhang,^a Yu-Jie Liu,^b Kai-Hui Li,^a Guang-Rui Yang ^a and Chong-Zhen Mei ^a ^*

^aInstitute of Environmental and Municipal Engineering, North China University of Water Conservancy and Electric Power, Zhengzhou 450011, People's Republic of China, and ^bSchool of Biochemical and Chemical Engineering, Nanyang Institute of Technology, Nanyang 473004, People's Republic of China
^*Correspondence e-mail: meichongzhen@163.com

(Received 19 June 2012; accepted 8 July 2012; online 14 July 2012)

In the title compound, [Ni(C₂₀H₁₃O₅P)(C₁₂H₁₀N₂)(H₂O)]_n, the Ni^II cation is coordinated by three O atoms from two 5-(diphenylphosphinoyl)isophthalate anions, two N atoms from two 1,2-bis(pyridin-4-yl)ethene ligands and one water molecule in a distorted octahedral geometry. Both 1,2-bis(pyridin-4-yl)ethene and 5-(diphenylphosphinoyl)isophthalate bridge the Ni^II cations to form polymeric layers parallel to (001). In the crystal, O—H⋯O hydrogen bonding links layers into a three-dimensional supramolecular structure.

Related literature

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ); Ockwig et al. (2005 ); Zang et al. (2011 ). For a related structure, see: Desiraju (2004 ).

Experimental

Crystal data

[Ni(C₂₀H₁₃O₅P)(C₁₂H₁₀N₂)(H₂O)]
M_r = 623.22
Monoclinic, P 2₁ /c
a = 10.1866 (3) Å
b = 13.6980 (3) Å
c = 21.7030 (6) Å
β = 111.174 (2)°
V = 2823.90 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.851, T_max = 0.864
11156 measured reflections
4971 independent reflections
3513 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.112
S = 0.99
4971 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.145 (3)
Ni1—N2ⁱ	2.134 (3)
Ni1—O1	2.140 (2)
Ni1—O2	2.120 (2)
Ni1—O3ⁱⁱ	2.039 (2)
Ni1—O1W	2.046 (2)
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5ⁱⁱⁱ	0.85	1.84	2.684 (3)	173
O1W—H1WB⋯O4ⁱⁱ	0.85	1.81	2.622 (3)	158
Symmetry codes: (ii) x+1, y, z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812031108/xu5570sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031108/xu5570Isup2.hkl

checkCIF report

Comment top

Supramolecular coordination assemblies have received much attention due to their discovery of interesting topologies and crystal packing motifs, and the potential applications as functional materials (Maspoch et al., 2007; Ockwig et al., 2005). A great number of carboxylate-based ligands have been successfully employed in the generation of many novel structures (Zang et al., 2011). To further explore various factors that influence the properties and construction of coordination compounds, we undertake synthetic and structural studies on one novel Ni(II) complex based on 5-(oxidediphenylphosphanyl)isophthalic acid (H2L) and 1,2-bis(pyridin-4-yl)ethene (bpe): [Ni(C₂₀H₁₃O₅P)(C₁₂H₁₀N₂)(H₂O)]_n (1).

X-ray crystallographic analysis revealed that the title compound crystallizes in monoclinic space group P2₁/c. As shown in Fig. 1, the asymmetric unit consists of one Ni^II atom, one L^2- anion, one bpe ligand and one coordinated water molecule. Each metal center is six-coordinated by three O atoms from two L^2- anions, one O atom from the coordinated water molecule and two N atoms from different 1,2-bis(pyridin-4-yl)ethene ligands. Four atoms O1W, O1, O2 and O3#1 comprise the equatorial plane; while N1, N2#2 occupies the axial position.

Each L^2- ligand acts as a µ₂-bridge linking two Ni^II atoms with one carboxylate group in monodentate fashion and the other one in chelating mode to form an infinite Ni- L^2- chain running along the a-axis. As depicted in Fig. 2, bpe ligand links adjacent chains running along the b-axis to form a (4,4)-layer with Ni1···Ni1 distance of 10.1866 (7) Å and 13.6980 (7) Å, respectively. Adjacent layers are associated together by O—H···O hydrogen bonds to achieve a three-dimensional supramolecular structure (Fig. 3). A further investigation reveals a more striking feature of title compound, i.e. two sets of symmetric related supamolecular structures are interlocked with each other to display a twofold interpenetrating architecture.

Related literature top

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2011). For a related structure, see: Desiraju (2004).

Experimental top

The title compound was synthesized hydrothermally in a Teflon-lined stainless teel container by heating a mixture of 5-(oxidediphenylphosphanyl)isophthalic acid (H2L) (0.0183 g, 0.05 mmol), 1,2-bis(4-pyridyl)ethane (bpe) (0.0091 g, 0.05 mmol), Ni(NO₃)₂.6H₂O (0.0146 g, 0.05 mmol) and NaOH (0.0040 g, 0.1 mmol) in 7 ml of distilled water at 130°C for 3 days, and then cooled to room temperature. Green block crystals of 1 were obtained in 78% yield based on nickel.

Structure description top

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2011). For a related structure, see: Desiraju (2004).

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: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Metal coordination and atom labeling in title compound (thermal ellipsoids at 50% probability level). Irrespective hydrogen atoms are omitted for clarity. Symmetry codes: #1: x + 1, y, z; #2: x, y - 1, z.
	Fig. 2. A view of the layer in compound 1
	Fig. 3. The three-dimensional supramolecular structure connected by hydrogen bonds. Dotted lines represent hydrogen bonds.

Poly[aqua(µ-1,2-bis(pyridin-4-yl)ethene-κ²N:N')[µ-5- (diphenylphosphinoyl)isophthalato- κ³O¹,O^1':O³]nickel(II)] top

Crystal data top

[Ni(C₂₀H₁₃O₅P)(C₁₂H₁₀N₂)(H₂O)]	F(000) = 1288
M_r = 623.22	D_x = 1.466 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4354 reflections
a = 10.1866 (3) Å	θ = 3.0–29.2°
b = 13.6980 (3) Å	µ = 0.79 mm⁻¹
c = 21.7030 (6) Å	T = 296 K
β = 111.174 (2)°	Block, green
V = 2823.90 (13) Å³	0.21 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4971 independent reflections
Radiation source: fine-focus sealed tube	3513 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→11
T_min = 0.851, T_max = 0.864	k = −16→10
11156 measured reflections	l = −25→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0554P)²] where P = (F_o² + 2F_c²)/3
4971 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Ni(C₂₀H₁₃O₅P)(C₁₂H₁₀N₂)(H₂O)]	V = 2823.90 (13) Å³
M_r = 623.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1866 (3) Å	µ = 0.79 mm⁻¹
b = 13.6980 (3) Å	T = 296 K
c = 21.7030 (6) Å	0.21 × 0.20 × 0.19 mm
β = 111.174 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4971 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3513 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.864	R_int = 0.043
11156 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.99	Δρ_max = 0.66 e Å⁻³
4971 reflections	Δρ_min = −0.33 e Å⁻³
379 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	0.42678 (4)	0.81298 (3)	0.86654 (2)	0.01907 (14)
O1	0.2074 (2)	0.81261 (16)	0.85164 (11)	0.0224 (5)
O2	0.3689 (2)	0.79683 (16)	0.95050 (11)	0.0248 (5)
O3	−0.3597 (2)	0.81335 (18)	0.91252 (11)	0.0258 (6)
O4	−0.2948 (2)	0.8308 (2)	0.82543 (12)	0.0509 (9)
O5	0.2692 (2)	0.75667 (19)	1.15849 (12)	0.0362 (7)
O1W	0.4295 (2)	0.82607 (17)	0.77310 (11)	0.0298 (6)
H1WA	0.3729	0.8019	0.7373	0.045*
H1WB	0.5171	0.8219	0.7804	0.045*
N1	0.4236 (3)	0.9691 (2)	0.87333 (16)	0.0285 (7)
N2	0.4261 (3)	1.65746 (19)	0.86079 (14)	0.0246 (7)
C1	0.1303 (3)	0.8117 (2)	0.94387 (16)	0.0196 (7)
C2	0.1668 (3)	0.7974 (2)	1.01139 (17)	0.0229 (8)
H2	0.2610	0.7912	1.0383	0.027*
C3	0.0630 (3)	0.7924 (2)	1.03897 (16)	0.0234 (8)
C4	−0.0783 (3)	0.8035 (2)	0.99786 (16)	0.0232 (8)
H4	−0.1478	0.8007	1.0162	0.028*
C5	−0.1164 (3)	0.8184 (2)	0.93095 (16)	0.0202 (7)
C6	−0.0103 (3)	0.8222 (2)	0.90399 (16)	0.0203 (7)
H6	−0.0345	0.8318	0.8588	0.024*
C7	0.2423 (3)	0.8062 (2)	0.91300 (17)	0.0202 (7)
C8	−0.2691 (3)	0.8216 (2)	0.88494 (16)	0.0211 (7)
C9	0.0171 (3)	0.8171 (3)	1.16355 (17)	0.0257 (8)
C10	−0.0222 (4)	0.7750 (3)	1.2120 (2)	0.0422 (11)
H10	−0.0102	0.7083	1.2199	0.051*
C11	−0.0793 (5)	0.8311 (3)	1.2489 (2)	0.0564 (13)
H11	−0.1076	0.8018	1.2808	0.068*
C12	−0.0943 (5)	0.9305 (3)	1.2386 (2)	0.0484 (11)
H12	−0.1304	0.9686	1.2643	0.058*
C13	−0.0560 (4)	0.9727 (3)	1.1908 (2)	0.0439 (11)
H13	−0.0673	1.0396	1.1835	0.053*
C14	−0.0007 (4)	0.9168 (3)	1.15294 (19)	0.0363 (10)
H14	0.0247	0.9463	1.1203	0.044*
C15	0.0537 (4)	0.6256 (3)	1.11215 (18)	0.0323 (9)
C16	−0.0846 (5)	0.5991 (3)	1.0956 (2)	0.0477 (11)
H16	−0.1515	0.6454	1.0956	0.057*
C17	−0.1247 (6)	0.5019 (4)	1.0788 (3)	0.0721 (16)
H17	−0.2179	0.4829	1.0679	0.087*
C18	−0.0238 (8)	0.4353 (4)	1.0787 (3)	0.0777 (18)
H18	−0.0503	0.3712	1.0662	0.093*
C19	0.1130 (7)	0.4611 (4)	1.0965 (3)	0.0748 (16)
H19	0.1799	0.4144	1.0973	0.090*
C20	0.1536 (5)	0.5558 (3)	1.1132 (2)	0.0511 (12)
H20	0.2477	0.5734	1.1253	0.061*
C21	0.3952 (4)	1.0150 (3)	0.92197 (19)	0.0360 (10)
H21	0.3723	0.9770	0.9522	0.043*
C22	0.3981 (4)	1.1145 (3)	0.9296 (2)	0.0395 (10)
H22	0.3784	1.1421	0.9645	0.047*
C23	0.4301 (4)	1.1727 (3)	0.8860 (2)	0.0350 (10)
C24	0.4573 (4)	1.1272 (3)	0.8351 (2)	0.0494 (12)
H24	0.4776	1.1641	0.8037	0.059*
C25	0.4542 (4)	1.0257 (3)	0.8312 (2)	0.0450 (11)
H25	0.4748	0.9963	0.7971	0.054*
C26	0.4401 (4)	1.2818 (3)	0.8951 (2)	0.0409 (10)
H26	0.4719	1.3061	0.9380	0.049*
C27	0.4072 (4)	1.3439 (3)	0.8468 (2)	0.0384 (10)
H27	0.3746	1.3186	0.8042	0.046*
C28	0.4170 (4)	1.4519 (3)	0.8536 (2)	0.0328 (9)
C29	0.5025 (4)	1.5007 (3)	0.9098 (2)	0.0410 (10)
H29	0.5582	1.4656	0.9467	0.049*
C30	0.5046 (4)	1.6028 (3)	0.91086 (19)	0.0368 (10)
H30	0.5643	1.6339	0.9487	0.044*
C31	0.3449 (4)	1.6099 (3)	0.8069 (2)	0.0397 (10)
H31	0.2893	1.6466	0.7709	0.048*
C32	0.3386 (4)	1.5088 (3)	0.8013 (2)	0.0437 (11)
H32	0.2810	1.4798	0.7622	0.052*
P1	0.11389 (9)	0.75019 (7)	1.12316 (4)	0.0244 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0152 (2)	0.0192 (2)	0.0231 (3)	0.00013 (18)	0.00720 (18)	−0.0006 (2)
O1	0.0184 (12)	0.0279 (13)	0.0209 (13)	−0.0002 (10)	0.0070 (10)	−0.0014 (11)
O2	0.0141 (12)	0.0354 (14)	0.0253 (13)	0.0012 (10)	0.0076 (10)	−0.0010 (11)
O3	0.0135 (11)	0.0425 (15)	0.0223 (13)	−0.0006 (11)	0.0076 (10)	0.0043 (12)
O4	0.0190 (13)	0.112 (3)	0.0192 (15)	0.0003 (15)	0.0046 (11)	0.0110 (16)
O5	0.0215 (13)	0.0544 (18)	0.0269 (14)	0.0031 (12)	0.0018 (11)	0.0106 (13)
O1W	0.0211 (12)	0.0436 (16)	0.0222 (13)	−0.0066 (11)	0.0047 (10)	−0.0044 (12)
N1	0.0241 (16)	0.0178 (15)	0.0431 (19)	−0.0017 (13)	0.0116 (15)	−0.0006 (15)
N2	0.0257 (16)	0.0193 (15)	0.0289 (17)	0.0034 (13)	0.0099 (14)	−0.0002 (14)
C1	0.0152 (16)	0.0185 (17)	0.0263 (18)	0.0002 (14)	0.0089 (14)	0.0014 (16)
C2	0.0137 (16)	0.026 (2)	0.0261 (19)	−0.0001 (14)	0.0038 (14)	0.0024 (16)
C3	0.0181 (17)	0.028 (2)	0.0219 (18)	0.0004 (15)	0.0050 (15)	0.0003 (16)
C4	0.0175 (17)	0.031 (2)	0.0234 (19)	0.0032 (15)	0.0097 (15)	0.0038 (17)
C5	0.0149 (16)	0.0217 (18)	0.0243 (18)	0.0000 (14)	0.0072 (14)	0.0025 (16)
C6	0.0200 (17)	0.0232 (18)	0.0177 (17)	0.0009 (15)	0.0070 (14)	0.0030 (15)
C7	0.0160 (17)	0.0172 (17)	0.026 (2)	−0.0020 (14)	0.0060 (15)	−0.0016 (16)
C8	0.0192 (17)	0.0251 (19)	0.0194 (18)	0.0020 (15)	0.0074 (14)	0.0018 (16)
C9	0.0241 (18)	0.032 (2)	0.0191 (18)	0.0006 (17)	0.0051 (15)	0.0009 (17)
C10	0.065 (3)	0.032 (2)	0.036 (2)	0.007 (2)	0.026 (2)	0.004 (2)
C11	0.084 (4)	0.061 (3)	0.043 (3)	0.014 (3)	0.045 (3)	0.009 (2)
C12	0.059 (3)	0.052 (3)	0.038 (2)	0.016 (2)	0.021 (2)	−0.005 (2)
C13	0.049 (3)	0.033 (2)	0.045 (3)	0.008 (2)	0.013 (2)	0.000 (2)
C14	0.044 (2)	0.034 (2)	0.032 (2)	0.0027 (19)	0.0146 (19)	0.0090 (19)
C15	0.044 (2)	0.030 (2)	0.027 (2)	0.0013 (19)	0.0182 (19)	0.0034 (18)
C16	0.053 (3)	0.037 (3)	0.051 (3)	−0.007 (2)	0.017 (2)	−0.004 (2)
C17	0.084 (4)	0.066 (4)	0.064 (4)	−0.031 (3)	0.023 (3)	−0.004 (3)
C18	0.131 (6)	0.032 (3)	0.070 (4)	−0.015 (4)	0.037 (4)	−0.005 (3)
C19	0.113 (5)	0.039 (3)	0.080 (4)	0.018 (3)	0.044 (4)	0.004 (3)
C20	0.067 (3)	0.038 (3)	0.058 (3)	0.009 (2)	0.035 (3)	0.008 (2)
C21	0.041 (2)	0.029 (2)	0.030 (2)	−0.0027 (18)	0.0025 (19)	−0.0016 (18)
C22	0.038 (2)	0.029 (2)	0.043 (3)	0.0035 (19)	0.005 (2)	−0.009 (2)
C23	0.029 (2)	0.026 (2)	0.052 (3)	−0.0003 (17)	0.0153 (19)	−0.005 (2)
C24	0.060 (3)	0.025 (2)	0.079 (4)	−0.009 (2)	0.044 (3)	0.009 (2)
C25	0.055 (3)	0.025 (2)	0.070 (3)	0.001 (2)	0.040 (3)	−0.004 (2)
C26	0.041 (2)	0.034 (2)	0.048 (3)	−0.0032 (19)	0.017 (2)	−0.005 (2)
C27	0.046 (2)	0.034 (2)	0.043 (3)	0.0019 (19)	0.025 (2)	0.007 (2)
C28	0.032 (2)	0.0233 (19)	0.050 (3)	−0.0040 (17)	0.022 (2)	−0.005 (2)
C29	0.049 (3)	0.025 (2)	0.045 (3)	0.0120 (19)	0.013 (2)	0.017 (2)
C30	0.040 (2)	0.031 (2)	0.032 (2)	−0.0011 (19)	0.0034 (19)	0.0004 (19)
C31	0.040 (2)	0.027 (2)	0.042 (3)	0.0008 (19)	0.003 (2)	0.001 (2)
C32	0.049 (3)	0.027 (2)	0.045 (3)	−0.004 (2)	0.005 (2)	−0.005 (2)
P1	0.0209 (5)	0.0307 (5)	0.0206 (5)	0.0027 (4)	0.0062 (4)	0.0039 (4)

Geometric parameters (Å, º) top

Ni1—N1	2.145 (3)	C12—C13	1.363 (6)
Ni1—N2ⁱ	2.134 (3)	C12—H12	0.9300
Ni1—O1	2.140 (2)	C13—C14	1.383 (5)
Ni1—O2	2.120 (2)	C13—H13	0.9300
Ni1—O3ⁱⁱ	2.039 (2)	C14—H14	0.9300
Ni1—O1W	2.046 (2)	C15—C16	1.372 (5)
O1—C7	1.251 (4)	C15—C20	1.390 (5)
O2—C7	1.259 (4)	C15—P1	1.799 (4)
O3—C8	1.273 (4)	C16—C17	1.401 (6)
O3—Ni1ⁱⁱⁱ	2.039 (2)	C16—H16	0.9300
O4—C8	1.228 (4)	C17—C18	1.375 (7)
O5—P1	1.491 (2)	C17—H17	0.9300
O1W—H1WA	0.8500	C18—C19	1.352 (7)
O1W—H1WB	0.8500	C18—H18	0.9300
N1—C25	1.320 (5)	C19—C20	1.371 (6)
N1—C21	1.347 (5)	C19—H19	0.9300
N2—C30	1.324 (4)	C20—H20	0.9300
N2—C31	1.333 (5)	C21—C22	1.371 (5)
N2—Ni1^iv	2.134 (3)	C21—H21	0.9300
C1—C6	1.387 (4)	C22—C23	1.366 (5)
C1—C2	1.389 (5)	C22—H22	0.9300
C1—C7	1.520 (4)	C23—C24	1.381 (6)
C2—C3	1.392 (4)	C23—C26	1.505 (5)
C2—H2	0.9300	C24—C25	1.393 (5)
C3—C4	1.401 (4)	C24—H24	0.9300
C3—P1	1.805 (3)	C25—H25	0.9300
C4—C5	1.376 (5)	C26—C27	1.296 (5)
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.403 (4)	C27—C28	1.487 (5)
C5—C8	1.516 (4)	C27—H27	0.9300
C6—H6	0.9300	C28—C32	1.370 (5)
C9—C10	1.380 (5)	C28—C29	1.388 (5)
C9—C14	1.387 (5)	C29—C30	1.399 (5)
C9—P1	1.790 (3)	C29—H29	0.9300
C10—C11	1.380 (5)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.389 (5)
C11—C12	1.380 (6)	C31—H31	0.9300
C11—H11	0.9300	C32—H32	0.9300

O3ⁱⁱ—Ni1—O1W	95.22 (9)	C14—C13—H13	119.8
O3ⁱⁱ—Ni1—O2	99.11 (9)	C13—C14—C9	120.2 (4)
O1W—Ni1—O2	165.63 (9)	C13—C14—H14	119.9
O3ⁱⁱ—Ni1—N2ⁱ	90.65 (10)	C9—C14—H14	119.9
O1W—Ni1—N2ⁱ	91.73 (10)	C16—C15—C20	119.9 (4)
O2—Ni1—N2ⁱ	87.14 (10)	C16—C15—P1	123.7 (3)
O3ⁱⁱ—Ni1—O1	160.95 (9)	C20—C15—P1	116.0 (3)
O1W—Ni1—O1	103.75 (9)	C15—C16—C17	119.7 (5)
O2—Ni1—O1	61.96 (8)	C15—C16—H16	120.2
N2ⁱ—Ni1—O1	90.45 (10)	C17—C16—H16	120.2
O3ⁱⁱ—Ni1—N1	90.23 (10)	C18—C17—C16	118.9 (5)
O1W—Ni1—N1	89.24 (11)	C18—C17—H17	120.5
O2—Ni1—N1	91.67 (10)	C16—C17—H17	120.5
N2ⁱ—Ni1—N1	178.62 (11)	C19—C18—C17	121.3 (5)
O1—Ni1—N1	88.38 (10)	C19—C18—H18	119.3
C7—O1—Ni1	87.68 (18)	C17—C18—H18	119.3
C7—O2—Ni1	88.37 (19)	C18—C19—C20	120.3 (5)
C8—O3—Ni1ⁱⁱⁱ	126.6 (2)	C18—C19—H19	119.9
Ni1—O1W—H1WA	128.7	C20—C19—H19	119.9
Ni1—O1W—H1WB	101.5	C19—C20—C15	119.9 (5)
H1WA—O1W—H1WB	117.6	C19—C20—H20	120.1
C25—N1—C21	116.1 (3)	C15—C20—H20	120.1
C25—N1—Ni1	121.6 (3)	N1—C21—C22	123.9 (4)
C21—N1—Ni1	122.2 (2)	N1—C21—H21	118.0
C30—N2—C31	116.3 (3)	C22—C21—H21	118.0
C30—N2—Ni1^iv	121.9 (2)	C23—C22—C21	119.8 (4)
C31—N2—Ni1^iv	121.8 (2)	C23—C22—H22	120.1
C6—C1—C2	119.7 (3)	C21—C22—H22	120.1
C6—C1—C7	120.0 (3)	C22—C23—C24	117.3 (3)
C2—C1—C7	120.0 (3)	C22—C23—C26	120.7 (4)
C1—C2—C3	120.3 (3)	C24—C23—C26	122.0 (4)
C1—C2—H2	119.8	C23—C24—C25	119.5 (4)
C3—C2—H2	119.8	C23—C24—H24	120.2
C2—C3—C4	119.1 (3)	C25—C24—H24	120.2
C2—C3—P1	117.8 (2)	N1—C25—C24	123.3 (4)
C4—C3—P1	122.2 (3)	N1—C25—H25	118.3
C5—C4—C3	121.4 (3)	C24—C25—H25	118.3
C5—C4—H4	119.3	C27—C26—C23	124.0 (4)
C3—C4—H4	119.3	C27—C26—H26	118.0
C4—C5—C6	118.6 (3)	C23—C26—H26	118.0
C4—C5—C8	122.1 (3)	C26—C27—C28	125.8 (4)
C6—C5—C8	119.1 (3)	C26—C27—H27	117.1
C1—C6—C5	120.9 (3)	C28—C27—H27	117.1
C1—C6—H6	119.6	C32—C28—C29	116.5 (3)
C5—C6—H6	119.6	C32—C28—C27	119.1 (4)
O1—C7—O2	121.8 (3)	C29—C28—C27	124.3 (4)
O1—C7—C1	119.7 (3)	C28—C29—C30	119.7 (4)
O2—C7—C1	118.5 (3)	C28—C29—H29	120.1
O4—C8—O3	126.0 (3)	C30—C29—H29	120.1
O4—C8—C5	118.3 (3)	N2—C30—C29	123.5 (4)
O3—C8—C5	115.7 (3)	N2—C30—H30	118.3
C10—C9—C14	118.8 (3)	C29—C30—H30	118.3
C10—C9—P1	121.5 (3)	N2—C31—C32	123.9 (4)
C14—C9—P1	119.0 (3)	N2—C31—H31	118.0
C11—C10—C9	120.7 (4)	C32—C31—H31	118.0
C11—C10—H10	119.7	C28—C32—C31	120.0 (4)
C9—C10—H10	119.7	C28—C32—H32	120.0
C12—C11—C10	120.0 (4)	C31—C32—H32	120.0
C12—C11—H11	120.0	O5—P1—C9	112.80 (16)
C10—C11—H11	120.0	O5—P1—C15	111.85 (16)
C13—C12—C11	119.8 (4)	C9—P1—C15	109.22 (16)
C13—C12—H12	120.1	O5—P1—C3	111.41 (15)
C11—C12—H12	120.1	C9—P1—C3	108.90 (16)
C12—C13—C14	120.5 (4)	C15—P1—C3	102.11 (16)
C12—C13—H13	119.8

O3ⁱⁱ—Ni1—O1—C7	−4.1 (4)	C20—C15—C16—C17	−1.1 (6)
O1W—Ni1—O1—C7	−178.89 (19)	P1—C15—C16—C17	170.9 (4)
O2—Ni1—O1—C7	2.69 (18)	C15—C16—C17—C18	−0.6 (7)
N2ⁱ—Ni1—O1—C7	89.2 (2)	C16—C17—C18—C19	2.1 (8)
N1—Ni1—O1—C7	−90.1 (2)	C17—C18—C19—C20	−1.9 (9)
O3ⁱⁱ—Ni1—O2—C7	175.10 (19)	C18—C19—C20—C15	0.2 (8)
O1W—Ni1—O2—C7	−8.9 (5)	C16—C15—C20—C19	1.3 (7)
N2ⁱ—Ni1—O2—C7	−94.70 (19)	P1—C15—C20—C19	−171.3 (4)
O1—Ni1—O2—C7	−2.67 (18)	C25—N1—C21—C22	−0.6 (5)
N1—Ni1—O2—C7	84.60 (19)	Ni1—N1—C21—C22	177.1 (3)
O3ⁱⁱ—Ni1—N1—C25	80.4 (3)	N1—C21—C22—C23	0.6 (6)
O1W—Ni1—N1—C25	−14.8 (3)	C21—C22—C23—C24	0.5 (6)
O2—Ni1—N1—C25	179.5 (3)	C21—C22—C23—C26	−177.3 (3)
O1—Ni1—N1—C25	−118.6 (3)	C22—C23—C24—C25	−1.4 (6)
O3ⁱⁱ—Ni1—N1—C21	−97.2 (3)	C26—C23—C24—C25	176.4 (4)
O1W—Ni1—N1—C21	167.6 (3)	C21—N1—C25—C24	−0.3 (6)
O2—Ni1—N1—C21	1.9 (3)	Ni1—N1—C25—C24	−178.1 (3)
O1—Ni1—N1—C21	63.8 (3)	C23—C24—C25—N1	1.3 (7)
C6—C1—C2—C3	0.7 (5)	C22—C23—C26—C27	−147.7 (4)
C7—C1—C2—C3	−173.4 (3)	C24—C23—C26—C27	34.7 (6)
C1—C2—C3—C4	−0.9 (5)	C23—C26—C27—C28	−179.3 (3)
C1—C2—C3—P1	168.1 (3)	C26—C27—C28—C32	−158.9 (4)
C2—C3—C4—C5	0.5 (5)	C26—C27—C28—C29	21.8 (6)
P1—C3—C4—C5	−168.0 (3)	C32—C28—C29—C30	0.2 (6)
C3—C4—C5—C6	0.2 (5)	C27—C28—C29—C30	179.6 (3)
C3—C4—C5—C8	174.6 (3)	C31—N2—C30—C29	−1.7 (6)
C2—C1—C6—C5	0.0 (5)	Ni1^iv—N2—C30—C29	177.3 (3)
C7—C1—C6—C5	174.1 (3)	C28—C29—C30—N2	1.4 (6)
C4—C5—C6—C1	−0.4 (5)	C30—N2—C31—C32	0.5 (6)
C8—C5—C6—C1	−175.0 (3)	Ni1^iv—N2—C31—C32	−178.5 (3)
Ni1—O1—C7—O2	−4.7 (3)	C29—C28—C32—C31	−1.3 (6)
Ni1—O1—C7—C1	174.1 (3)	C27—C28—C32—C31	179.3 (3)
Ni1—O2—C7—O1	4.7 (3)	N2—C31—C32—C28	1.1 (7)
Ni1—O2—C7—C1	−174.1 (3)	C10—C9—P1—O5	−88.3 (3)
C6—C1—C7—O1	1.1 (5)	C14—C9—P1—O5	82.1 (3)
C2—C1—C7—O1	175.2 (3)	C10—C9—P1—C15	36.7 (4)
C6—C1—C7—O2	179.9 (3)	C14—C9—P1—C15	−152.9 (3)
C2—C1—C7—O2	−6.0 (5)	C10—C9—P1—C3	147.5 (3)
Ni1ⁱⁱⁱ—O3—C8—O4	−0.1 (5)	C14—C9—P1—C3	−42.1 (3)
Ni1ⁱⁱⁱ—O3—C8—C5	−179.3 (2)	C16—C15—P1—O5	164.2 (3)
C4—C5—C8—O4	−176.7 (3)	C20—C15—P1—O5	−23.6 (4)
C6—C5—C8—O4	−2.4 (5)	C16—C15—P1—C9	38.6 (4)
C4—C5—C8—O3	2.5 (5)	C20—C15—P1—C9	−149.2 (3)
C6—C5—C8—O3	176.9 (3)	C16—C15—P1—C3	−76.6 (4)
C14—C9—C10—C11	0.5 (6)	C20—C15—P1—C3	95.6 (3)
P1—C9—C10—C11	171.0 (3)	C2—C3—P1—O5	18.4 (3)
C9—C10—C11—C12	−1.6 (7)	C4—C3—P1—O5	−172.9 (3)
C10—C11—C12—C13	1.7 (7)	C2—C3—P1—C9	143.5 (3)
C11—C12—C13—C14	−0.8 (7)	C4—C3—P1—C9	−47.9 (3)
C12—C13—C14—C9	−0.3 (6)	C2—C3—P1—C15	−101.1 (3)
C10—C9—C14—C13	0.4 (6)	C4—C3—P1—C15	67.5 (3)
P1—C9—C14—C13	−170.3 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5^v	0.85	1.84	2.684 (3)	173
O1W—H1WB···O4ⁱⁱ	0.85	1.81	2.622 (3)	158

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₁₃O₅P)(C₁₂H₁₀N₂)(H₂O)]
M_r	623.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.1866 (3), 13.6980 (3), 21.7030 (6)
β (°)	111.174 (2)
V (Å³)	2823.90 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.21 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.851, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	11156, 4971, 3513
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.112, 0.99
No. of reflections	4971
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2010).

Selected bond lengths (Å) top

Ni1—N1	2.145 (3)	Ni1—O2	2.120 (2)
Ni1—N2ⁱ	2.134 (3)	Ni1—O3ⁱⁱ	2.039 (2)
Ni1—O1	2.140 (2)	Ni1—O1W	2.046 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5ⁱⁱⁱ	0.85	1.84	2.684 (3)	173
O1W—H1WB···O4ⁱⁱ	0.85	1.81	2.622 (3)	158

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

Acknowledgements

This work was supported by the International Technology Cooperation Project of the Science and Technology Department of Henan Province of China (grant No. 124300510050).

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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