Bis[1-hydroxy­ethyl­idenediphosphon­ato(1−)](1,10-phenanthroline)nickel(II) mono­hydrate

Zhang, X.; Ge, C.; Zhang, X.; Liu, Q.

doi:10.1107/S1600536807065129

metal-organic compounds

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Volume 64| Part 2| February 2008| Page m398

doi:10.1107/S1600536807065129

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Bis[1-hydroxyethylidenediphosphonato(1−)](1,10-phenanthroline)nickel(II) monohydrate

Xiangdong Zhang,^a ^* Chunhua Ge,^a Xiaoyan Zhang ^a and Qitao Liu ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
^*Correspondence e-mail: xdzhang@lnu.edu.cn

(Received 7 November 2007; accepted 2 December 2007; online 23 January 2008)

In the mononuclear title compound, [Ni(C₂H₆O₇P₂)₂(C₁₂H₈N₂)]·H₂O, the Ni^II atom (site symmetry 2) is bonded to two phosphate-based O,O′-bidentate chelate ligands and one N,N′-bidentate 1,10-phenanthroline ligand, resulting in a slightly distorted cis-NiN₂O₄ octahedral geometry. In the crystal structure, pairs of complexes are linked by double hydrogen bonds, forming a one-dimensional chain-like structure. Aromatic π–π stacking interactions [centroid–centroid separation = 3.768 (2) Å] and further hydrogen bonds generate a two-dimensional structure. The water O atom also lies on a crystallographic twofold axis.

Related literature

For related literature, see: Song et al. (1999 ); Xiang et al. (2007 ).

Experimental

Crystal data

[Ni(C₂H₆O₇P₂)₂(C₁₂H₈N₂)]·H₂O
M_r = 664.95
Monoclinic, C 2/c
a = 17.108 (2) Å
b = 18.572 (2) Å
c = 7.5142 (9) Å
β = 90.164 (2)°
V = 2387.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 293 (2) K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.770, T_max = 0.819
6424 measured reflections
2268 independent reflections
1857 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.101
S = 1.06
2268 reflections
187 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.059 (3)
Ni1—O3	2.065 (3)
Ni1—O4	2.109 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O7	0.85 (6)	1.93 (6)	2.758 (5)	166 (6)
O2—H2A⋯O1Wⁱ	0.84 (4)	1.91 (4)	2.748 (4)	175 (6)
O6—H6A⋯O4ⁱⁱ	0.83 (4)	1.82 (4)	2.644 (3)	171 (5)
O7—H7⋯O4	0.82	2.47	2.894 (4)	113
O7—H7⋯O3ⁱⁱⁱ	0.82	2.08	2.889 (4)	169
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x, y, -z+{\script{3\over 2}}]$ ; (iii) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065129/hb2645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807065129/hb2645Isup2.hkl

checkCIF report

Comment top

Metal–phosphonate compounds are of current interest due to their fascinating topologies and novel physical properties (e.g. Song et al. 1999; Xiang et al. 2007).

In the title compound, (I), the Ni^II ion with site symmetry 2, is chelated by four oxygen atoms from two phosphate-containing O,O-chelate ligands and two nitrogen atoms from an N,N-chelating 1,10-phenanthroline (phen) ligand to generate a cis-NiN₂O₄ distorted octahedral coordination geometry (Fig. 1, Table 1).

Intermolecular hydrogen bond interactions (Table 2) occur between the phosphate ligands Each complex is connected with its neighbours by hydrogen bonds to form one-dimensional chain (Fig. 2). Aromatic π-π stacking interactions with distance between ring centroids of 3.768 (2) Å extend the width of the chain. Water molecules between those chains act as bridges to generate two dimensional structure through further O-H···O hydrogen bonds

Related literature top

For related literature, see: Song et al. (1999); Xiang et al. (2007).

Experimental top

1,10-Phenanthroline (1 mmol), Ni(NO₃)₂.6H₂O (2 mmol), 1-hydroxyethylidenediphosphonic acid (0.2 ml) and ethanol/H₂O (v:v = 1:3, 40 ml) were mixed. The resulting mixture was heated and stirred for 4 h and the solution was filtered. By slow evaporation of the solvent, blue blocks of (I) were obtained after several months.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. View of the molecular structure of (I), showing displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity. Atoms with the suffix A are generated by the symmetry operation (-x, y, 1/2 - z).
	Fig. 2. Two-dimensional structure of (I) formed by π-π stacking interactions between hydrogen bonded chains.

Bis[1-hydroxyethylidenediphosphonato(1-)](1,10-phenanthroline)nickel(II) monohydrate top

Crystal data top

[Ni(C₂H₆O₇P₂)₂(C₁₂H₈N₂)]·H₂O	F(000) = 1360
M_r = 664.95	D_x = 1.850 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 542 reflections
a = 17.108 (2) Å	θ = 2.8–24.7°
b = 18.572 (2) Å	µ = 1.16 mm⁻¹
c = 7.5142 (9) Å	T = 293 K
β = 90.164 (2)°	Block, blue
V = 2387.5 (5) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2268 independent reflections
Radiation source: fine-focus sealed tube	1857 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 25.7°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→20
T_min = 0.770, T_max = 0.819	k = −14→22
6424 measured reflections	l = −8→9

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)] = 0.045	Hydrogen site location: difmap and geom
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.041P)² + 5.7735P] where P = (F_o² + 2F_c²)/3
2268 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.53 e Å⁻³
3 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Ni(C₂H₆O₇P₂)₂(C₁₂H₈N₂)]·H₂O	V = 2387.5 (5) Å³
M_r = 664.95	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.108 (2) Å	µ = 1.16 mm⁻¹
b = 18.572 (2) Å	T = 293 K
c = 7.5142 (9) Å	0.22 × 0.20 × 0.18 mm
β = 90.164 (2)°

Data collection top

Bruker SMART CCD diffractometer	2268 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1857 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.819	R_int = 0.043
6424 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.53 e Å⁻³
2268 reflections	Δρ_min = −0.32 e Å⁻³
187 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
H2A	0.093 (2)	0.050 (3)	0.236 (8)	0.07 (2)*
H6A	0.0606 (18)	0.256 (3)	0.852 (6)	0.044 (15)*
O1W	0.0000	0.0069 (3)	0.7500	0.0356 (11)
O7	0.03755 (15)	0.11993 (14)	0.5280 (4)	0.0245 (6)
H7	0.0046	0.1455	0.4800	0.037*
O5	0.17574 (14)	0.28983 (14)	0.5476 (3)	0.0220 (6)
Ni1	0.0000	0.27786 (4)	0.2500	0.01343 (19)
P1	0.13862 (5)	0.15397 (5)	0.27824 (13)	0.0161 (2)
P2	0.10427 (5)	0.24696 (6)	0.59910 (12)	0.0157 (2)
O3	0.07673 (14)	0.19644 (14)	0.1833 (3)	0.0192 (6)
O4	0.02826 (14)	0.27551 (13)	0.5233 (3)	0.0159 (6)
N1	0.07336 (17)	0.36185 (17)	0.1867 (4)	0.0175 (7)
O2	0.13487 (17)	0.07260 (16)	0.2226 (4)	0.0295 (7)
O1	0.22184 (14)	0.17731 (16)	0.2446 (4)	0.0265 (7)
O6	0.10100 (15)	0.24085 (17)	0.8048 (3)	0.0257 (7)
C5	0.0390 (2)	0.4269 (2)	0.2147 (5)	0.0177 (8)
C1	0.1439 (2)	0.3607 (2)	0.1143 (5)	0.0219 (9)
H1	0.1674	0.3164	0.0931	0.026*
C2	0.1846 (2)	0.4237 (2)	0.0684 (5)	0.0293 (10)
H2	0.2338	0.4210	0.0164	0.035*
C8	0.1142 (2)	0.1545 (2)	0.5157 (5)	0.0177 (8)
C6	0.0362 (3)	0.5580 (2)	0.2142 (6)	0.0347 (11)
H6	0.0605	0.6016	0.1889	0.042*
C4	0.0760 (3)	0.4923 (2)	0.1766 (5)	0.0258 (9)
C7	0.1711 (2)	0.1109 (2)	0.6265 (6)	0.0293 (10)
H7A	0.1533	0.1091	0.7475	0.044*
H7B	0.2218	0.1330	0.6225	0.044*
H7C	0.1743	0.0628	0.5798	0.044*
C3	0.1510 (3)	0.4888 (2)	0.1011 (6)	0.0317 (11)
H3	0.1776	0.5310	0.0734	0.038*
H1WA	0.014 (5)	0.036 (3)	0.669 (8)	0.14 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.042 (3)	0.025 (3)	0.040 (3)	0.000	−0.001 (2)	0.000
O7	0.0212 (14)	0.0220 (15)	0.0303 (17)	−0.0014 (12)	0.0010 (12)	0.0085 (13)
O5	0.0159 (13)	0.0305 (17)	0.0198 (14)	−0.0035 (12)	0.0005 (11)	−0.0011 (12)
Ni1	0.0139 (3)	0.0141 (4)	0.0122 (3)	0.000	−0.0011 (3)	0.000
P1	0.0134 (5)	0.0183 (5)	0.0165 (5)	0.0021 (4)	−0.0013 (4)	−0.0034 (4)
P2	0.0128 (5)	0.0219 (6)	0.0124 (5)	0.0008 (4)	−0.0010 (4)	−0.0011 (4)
O3	0.0180 (13)	0.0239 (15)	0.0156 (14)	0.0043 (11)	0.0016 (11)	−0.0013 (11)
O4	0.0153 (13)	0.0201 (14)	0.0122 (13)	0.0008 (11)	−0.0010 (10)	−0.0008 (11)
N1	0.0176 (16)	0.0212 (18)	0.0136 (16)	−0.0013 (14)	−0.0031 (13)	0.0015 (13)
O2	0.0306 (17)	0.0215 (16)	0.0365 (18)	0.0042 (14)	0.0010 (14)	−0.0063 (14)
O1	0.0150 (13)	0.0427 (18)	0.0218 (15)	−0.0044 (13)	0.0006 (11)	−0.0085 (13)
O6	0.0179 (14)	0.0456 (19)	0.0134 (14)	0.0072 (13)	−0.0002 (12)	−0.0013 (13)
C5	0.028 (2)	0.013 (2)	0.0125 (19)	−0.0014 (16)	−0.0047 (16)	−0.0007 (15)
C1	0.0205 (19)	0.026 (2)	0.019 (2)	−0.0005 (17)	−0.0023 (16)	−0.0004 (17)
C2	0.023 (2)	0.043 (3)	0.022 (2)	−0.009 (2)	0.0021 (17)	0.005 (2)
C8	0.0162 (18)	0.017 (2)	0.020 (2)	0.0003 (15)	−0.0008 (15)	0.0045 (16)
C6	0.051 (3)	0.015 (2)	0.038 (3)	−0.009 (2)	−0.007 (2)	0.0020 (19)
C4	0.037 (2)	0.021 (2)	0.019 (2)	−0.0084 (19)	−0.0071 (18)	0.0027 (17)
C7	0.026 (2)	0.034 (3)	0.028 (2)	0.0110 (19)	−0.0049 (18)	0.006 (2)
C3	0.037 (3)	0.028 (3)	0.030 (2)	−0.014 (2)	−0.003 (2)	0.005 (2)

Geometric parameters (Å, º) top

O1W—H1WA	0.85 (6)	N1—C5	1.360 (5)
O7—C8	1.464 (4)	O2—H2A	0.84 (2)
O7—H7	0.8200	O6—H6A	0.83 (4)
O5—P2	1.511 (3)	C5—C4	1.400 (5)
Ni1—N1	2.059 (3)	C5—C5ⁱ	1.438 (7)
Ni1—N1ⁱ	2.059 (3)	C1—C2	1.406 (6)
Ni1—O3ⁱ	2.065 (3)	C1—H1	0.9300
Ni1—O3	2.065 (3)	C2—C3	1.362 (6)
Ni1—O4	2.109 (2)	C2—H2	0.9300
Ni1—O4ⁱ	2.109 (2)	C8—C7	1.514 (5)
P1—O3	1.499 (3)	C6—C6ⁱ	1.352 (9)
P1—O1	1.510 (3)	C6—C4	1.426 (6)
P1—O2	1.569 (3)	C6—H6	0.9300
P1—C8	1.834 (4)	C4—C3	1.405 (6)
P2—O4	1.514 (3)	C7—H7A	0.9600
P2—O6	1.551 (3)	C7—H7B	0.9600
P2—C8	1.836 (4)	C7—H7C	0.9600
N1—C1	1.326 (5)	C3—H3	0.9300

C8—O7—H7	109.5	P1—O2—H2A	119 (4)
N1—Ni1—N1ⁱ	81.47 (17)	P2—O6—H6A	116 (3)
N1—Ni1—O3ⁱ	177.81 (11)	N1—C5—C4	122.9 (4)
N1ⁱ—Ni1—O3ⁱ	96.34 (11)	N1—C5—C5ⁱ	117.3 (2)
N1—Ni1—O3	96.34 (11)	C4—C5—C5ⁱ	119.8 (2)
N1ⁱ—Ni1—O3	177.81 (11)	N1—C1—C2	122.6 (4)
O3ⁱ—Ni1—O3	85.85 (14)	N1—C1—H1	118.7
N1—Ni1—O4	95.88 (11)	C2—C1—H1	118.7
N1ⁱ—Ni1—O4	85.92 (11)	C3—C2—C1	119.0 (4)
O3ⁱ—Ni1—O4	83.84 (10)	C3—C2—H2	120.5
O3—Ni1—O4	94.41 (9)	C1—C2—H2	120.5
N1—Ni1—O4ⁱ	85.92 (11)	O7—C8—C7	107.8 (3)
N1ⁱ—Ni1—O4ⁱ	95.88 (11)	O7—C8—P1	105.4 (2)
O3ⁱ—Ni1—O4ⁱ	94.41 (9)	C7—C8—P1	112.6 (3)
O3—Ni1—O4ⁱ	83.84 (10)	O7—C8—P2	107.7 (2)
O4—Ni1—O4ⁱ	177.63 (14)	C7—C8—P2	111.9 (3)
O3—P1—O1	115.74 (16)	P1—C8—P2	111.03 (19)
O3—P1—O2	110.59 (16)	C6ⁱ—C6—C4	121.2 (2)
O1—P1—O2	105.64 (16)	C6ⁱ—C6—H6	119.4
O3—P1—C8	107.32 (15)	C4—C6—H6	119.4
O1—P1—C8	112.24 (16)	C5—C4—C3	117.2 (4)
O2—P1—C8	104.79 (17)	C5—C4—C6	119.0 (4)
O5—P2—O4	114.45 (15)	C3—C4—C6	123.8 (4)
O5—P2—O6	109.01 (15)	C8—C7—H7A	109.5
O4—P2—O6	111.53 (14)	C8—C7—H7B	109.5
O5—P2—C8	109.23 (16)	H7A—C7—H7B	109.5
O4—P2—C8	106.25 (16)	C8—C7—H7C	109.5
O6—P2—C8	105.99 (17)	H7A—C7—H7C	109.5
P1—O3—Ni1	135.93 (15)	H7B—C7—H7C	109.5
P2—O4—Ni1	124.60 (14)	C2—C3—C4	120.0 (4)
C1—N1—C5	118.2 (3)	C2—C3—H3	120.0
C1—N1—Ni1	129.7 (3)	C4—C3—H3	120.0
C5—N1—Ni1	111.9 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O7	0.85 (6)	1.93 (6)	2.758 (5)	166 (6)
O2—H2A···O1Wⁱⁱ	0.84 (4)	1.91 (4)	2.748 (4)	175 (6)
O6—H6A···O4ⁱⁱⁱ	0.83 (4)	1.82 (4)	2.644 (3)	171 (5)
O7—H7···O4	0.82	2.47	2.894 (4)	113
O7—H7···O3ⁱ	0.82	2.08	2.889 (4)	169

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂H₆O₇P₂)₂(C₁₂H₈N₂)]·H₂O
M_r	664.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	17.108 (2), 18.572 (2), 7.5142 (9)
β (°)	90.164 (2)
V (Å³)	2387.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.770, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	6424, 2268, 1857
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.101, 1.06
No. of reflections	2268
No. of parameters	187
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)	0.53, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Selected bond lengths (Å) top

Ni1—N1	2.059 (3)	Ni1—O4	2.109 (2)
Ni1—O3	2.065 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O7	0.85 (6)	1.93 (6)	2.758 (5)	166 (6)
O2—H2A···O1Wⁱ	0.84 (4)	1.91 (4)	2.748 (4)	175 (6)
O6—H6A···O4ⁱⁱ	0.83 (4)	1.82 (4)	2.644 (3)	171 (5)
O7—H7···O4	0.82	2.47	2.894 (4)	113
O7—H7···O3ⁱⁱⁱ	0.82	2.08	2.889 (4)	169

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

Acknowledgements

This project is supported by the Natural Science Foundation of the Education Bureau of Liaoning Province.

References

Bruker (2001). SMART, SAINT, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Song, H.-H., Zheng, L.-M., Lin, C.-H., Wang, S.-L., Xin, X.-Q. & Gao, S. (1999). Chem. Mater. 11, 2382–2388. Web of Science CSD CrossRef CAS Google Scholar
Xiang, J., Li, M., Wu, S., Yuan, L.-J. & Sun, J. (2007). J. Mol. Struct. 826, 143–149. Web of Science CSD CrossRef CAS Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[1-hy­droxy­ethyl­idenedi­phosphon­ato(1−)](1,10-phenanthroline)nickel(II) mono­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[1-hydroxyethylidenediphosphonato(1−)](1,10-phenanthroline)nickel(II) monohydrate