Tetra­aqua­bis(2-oxo-1,2-dihydro­quinoline-4-carboxyl­ato-κO4)nickel(II)

Yuan, G.; Qin, J.-S.; Su, Z.-M.; Shao, K.-Z.; Fu, Y.-M.

doi:10.1107/S1600536807065671

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m389-m390

doi:10.1107/S1600536807065671

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Tetraaquabis(2-oxo-1,2-dihydroquinoline-4-carboxylato-κO⁴)nickel(II)

Gang Yuan,^a Jun-Sheng Qin,^a Zhong-Min Su,^a ^* Kui-Zhan Shao ^a and Yao-Mei Fu ^a

^aInstitute of Functional Materials Chemistry, Department of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: zmsu@nenu.edu.cn

(Received 13 November 2007; accepted 5 December 2007; online 23 January 2008)

In the title compound, [Ni(C₁₀H₆NO₃)₂(H₂O)₄], the central Ni^II atom is located on an inversion center and coordinated in a slightly distorted octahedral geometry by two O atoms from two 2-oxo-1,2-dihydroquinoline-4-carboxylate ligands and four water molecules, all of which act as monodentate ligands. The crystal structure features an extensive network of intermolecular hydrogen-bonding interactions (O—H⋯O and N—H⋯O) and offset face-to-face π–π stacking interactions [centroid–centroid distances = 3.525 (3) and 3.281 (5) Å].

Related literature

For related literature, see: Bai et al. (2007 ); Bu et al. (2005 ); Liu (2007 ); Pang et al. (2007 ); Wu et al. (2007 ); Xiong et al. (2000 ); Zhang et al. (2007 ).

Experimental

Crystal data

[Ni(C₁₀H₆NO₃)₂(H₂O)₄]
M_r = 507.07
Triclinic, $[P \overline 1]$
a = 7.105 (5) Å
b = 8.507 (5) Å
c = 9.216 (5) Å
α = 108.723 (5)°
β = 108.396 (5)°
γ = 90.840 (5)°
V = 496.4 (5) Å³
Z = 1
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 293 (2) K
0.5 × 0.4 × 0.3 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.601, T_max = 0.721
3041 measured reflections
2250 independent reflections
2064 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.121
S = 1.02
2250 reflections
151 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	2.007 (2)
Ni1—O1W	2.083 (2)
Ni1—O2W	2.117 (2)

O1—Ni1—O1W	89.31 (10)
O1—Ni1—O1Wⁱ	90.69 (10)
O1—Ni1—O2W	88.35 (8)
O1W—Ni1—O2W	89.05 (9)
O1Wⁱ—Ni1—O2W	90.95 (9)
O1—Ni1—O2Wⁱ	91.65 (8)
Symmetry code: (i) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2Wⁱⁱ	0.86	2.18	3.031 (3)	173
O1W—H1⋯O2ⁱⁱⁱ	0.85	1.94	2.783 (3)	169
O1W—H2⋯O3^iv	0.85	1.89	2.722 (3)	164
O2W—H3⋯O2ⁱ	0.85	1.90	2.709 (3)	158
O2W—H4⋯O3^v	0.85	1.98	2.767 (3)	154
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y, z; (iv) -x+1, -y+2, -z; (v) x, y, z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990 ); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065671/hy2104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807065671/hy2104Isup2.hkl

checkCIF report

Comment top

Recently, the complexes based on quinoline-4-carboxylic acid have been reported (Bu et al., 2005; Xiong et al., 2000). However, the compounds built from 2-oxo-1,2-dihydroquinoline-4-carboxylic acid (dhqc) and transition metals have not been reported. When 2-hydroquinoline-4-carboxylic acid (hqc) and NiCl₂ were employed as starting materials, the title compound, as shown in Fig. 1, was obtained. X-ray diffraction analysis has revealed that hqc exists mainly in the form of its tautomer dhqc, because the proton transfers from hydroxyl O atom to N atom under alkaline condition. Similar to the most mononuclear Ni complexes reported previously (Bai et al., 2007; Liu, 2007; Pang et al., 2007; Wu et al., 2007; Zhang et al., 2007), the Ni^II atom in the title compound, lying on an inversion center, is six-coordinated by four water molecules and two O atoms from two dhqc ligands (Table 1), forming a slightly distorted octahedral geometry. The molecules are linked into a three-dimensional network by a combination of intermolecular hydrogen bonds (O–H···O and N–H···O) (Table 2) and offset face-to-face π–π stacking interactions [centroid-to-centroid distances 3.525 (3) and 3.281 (5) Å].

Related literature top

For related literature, see: Bai et al. (2007); Bu et al. (2005); Liu (2007); Pang et al. (2007); Wu et al. (2007); Xiong et al. (2000); Zhang et al. (2007).

Experimental top

A mixture of 2-hydroxyquinoline-4-carboxylic acid (0.945 g, 5 mmol), NaOH(0.4 g, 10 mmol) and NiCl₂.6H₂O (2.3 g,10 mmol) in water (50 ml) was boiled for 20 min with stirring. Then the mixture was cooled to room temperature. The resulting solution was filtered and allowed to stand. After a week, green crystals of the title compound were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990); software used to prepare material for publication: SHELXTL-Plus (Siemens, 1990).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1 - x, 2 - y, 1 - z.]

Tetraaquabis(2-oxo-1,2-dihydroquinoline-4-carboxylato-κO⁴)nickel(II) top

Crystal data top

[Ni(C₁₀H₆NO₃)₂(H₂O)₄]	Z = 1
M_r = 507.07	F(000) = 262
Triclinic, P1	D_x = 1.696 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.105 (5) Å	Cell parameters from 2250 reflections
b = 8.507 (5) Å	θ = 1.3–26.0°
c = 9.216 (5) Å	µ = 1.04 mm⁻¹
α = 108.723 (5)°	T = 293 K
β = 108.396 (5)°	Block, green
γ = 90.840 (5)°	0.5 × 0.4 × 0.3 mm
V = 496.4 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2250 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.601, T_max = 0.721	k = −8→11
3041 measured reflections	l = −12→7

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0726P)² + 0.4272P] where P = (F_o² + 2F_c²)/3
2250 reflections	(Δ/σ)_max = 0.001
151 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Ni(C₁₀H₆NO₃)₂(H₂O)₄]	γ = 90.840 (5)°
M_r = 507.07	V = 496.4 (5) Å³
Triclinic, P1	Z = 1
a = 7.105 (5) Å	Mo Kα radiation
b = 8.507 (5) Å	µ = 1.04 mm⁻¹
c = 9.216 (5) Å	T = 293 K
α = 108.723 (5)°	0.5 × 0.4 × 0.3 mm
β = 108.396 (5)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2250 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2064 reflections with I > 2σ(I)
T_min = 0.601, T_max = 0.721	R_int = 0.015
3041 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 0.40 e Å⁻³
2250 reflections	Δρ_min = −0.57 e Å⁻³
151 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	1.0000	0.5000	0.02024 (16)
C1	0.6765 (4)	0.6477 (3)	−0.1760 (3)	0.0260 (5)
C2	0.6843 (4)	0.7807 (3)	−0.0285 (3)	0.0276 (6)
H2A	0.6609	0.8868	−0.0322	0.033*
C3	0.7249 (4)	0.7538 (3)	0.1145 (3)	0.0234 (5)
C4	0.7688 (4)	0.5932 (3)	0.1253 (3)	0.0241 (5)
C5	0.8169 (4)	0.5563 (4)	0.2709 (3)	0.0316 (6)
H5A	0.8186	0.6386	0.3666	0.038*
C6	0.8610 (5)	0.4004 (4)	0.2722 (4)	0.0363 (7)
H6A	0.8936	0.3779	0.3689	0.044*
C7	0.8573 (4)	0.2754 (4)	0.1295 (4)	0.0342 (6)
H7A	0.8882	0.1702	0.1320	0.041*
C8	0.8084 (4)	0.3057 (3)	−0.0152 (3)	0.0289 (6)
H8A	0.8052	0.2214	−0.1102	0.035*
C9	0.7636 (4)	0.4648 (3)	−0.0176 (3)	0.0233 (5)
C10	0.7168 (4)	0.8914 (3)	0.2641 (3)	0.0244 (5)
N1	0.7143 (3)	0.4972 (3)	−0.1615 (3)	0.0250 (5)
H1A	0.7072	0.4158	−0.2483	0.030*
O1	0.5726 (3)	0.8651 (3)	0.3072 (2)	0.0319 (5)
O2	0.8452 (3)	1.0169 (3)	0.3306 (3)	0.0337 (5)
O3	0.6381 (3)	0.6659 (3)	−0.3117 (2)	0.0342 (5)
O1W	0.2409 (3)	1.0448 (3)	0.3421 (3)	0.0331 (5)
H1	0.1249	1.0296	0.3471	0.050*
H2	0.2548	1.1369	0.3265	0.050*
O2W	0.3413 (3)	0.7783 (2)	0.4826 (2)	0.0274 (4)
H3	0.2601	0.8200	0.5308	0.041*
H4	0.4010	0.7217	0.5403	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0210 (3)	0.0197 (2)	0.0201 (2)	0.00347 (17)	0.01005 (17)	0.00379 (17)
C1	0.0249 (13)	0.0306 (14)	0.0230 (12)	0.0038 (10)	0.0085 (10)	0.0095 (11)
C2	0.0327 (14)	0.0266 (13)	0.0272 (13)	0.0085 (11)	0.0138 (11)	0.0103 (11)
C3	0.0207 (12)	0.0268 (13)	0.0229 (12)	0.0038 (10)	0.0106 (10)	0.0056 (10)
C4	0.0230 (12)	0.0274 (13)	0.0232 (12)	0.0039 (10)	0.0097 (10)	0.0085 (10)
C5	0.0353 (15)	0.0379 (16)	0.0218 (12)	0.0064 (12)	0.0103 (11)	0.0100 (11)
C6	0.0383 (16)	0.0423 (17)	0.0331 (15)	0.0042 (13)	0.0087 (12)	0.0226 (13)
C7	0.0323 (15)	0.0287 (14)	0.0425 (16)	0.0034 (11)	0.0071 (12)	0.0189 (13)
C8	0.0274 (13)	0.0241 (13)	0.0306 (13)	0.0029 (10)	0.0074 (11)	0.0059 (11)
C9	0.0196 (12)	0.0261 (13)	0.0237 (11)	0.0026 (10)	0.0070 (9)	0.0081 (10)
C10	0.0254 (13)	0.0264 (13)	0.0230 (12)	0.0083 (10)	0.0117 (10)	0.0070 (10)
N1	0.0294 (12)	0.0237 (11)	0.0191 (10)	0.0037 (9)	0.0089 (9)	0.0031 (8)
O1	0.0308 (10)	0.0314 (11)	0.0293 (10)	−0.0013 (8)	0.0176 (8)	−0.0020 (8)
O2	0.0316 (11)	0.0295 (11)	0.0388 (11)	−0.0002 (8)	0.0197 (9)	0.0026 (9)
O3	0.0412 (12)	0.0395 (12)	0.0251 (9)	0.0082 (9)	0.0111 (9)	0.0154 (9)
O1W	0.0257 (10)	0.0366 (11)	0.0390 (11)	0.0058 (8)	0.0100 (8)	0.0165 (9)
O2W	0.0304 (10)	0.0278 (10)	0.0263 (9)	0.0055 (8)	0.0127 (8)	0.0094 (8)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	2.007 (2)	C5—H5A	0.9300
Ni1—O1	2.007 (2)	C6—C7	1.393 (5)
Ni1—O1W	2.083 (2)	C6—H6A	0.9300
Ni1—O1Wⁱ	2.083 (2)	C7—C8	1.377 (4)
Ni1—O2W	2.117 (2)	C7—H7A	0.9300
Ni1—O2Wⁱ	2.117 (2)	C8—C9	1.401 (4)
C1—O3	1.254 (3)	C8—H8A	0.9300
C1—N1	1.351 (4)	C9—N1	1.379 (3)
C1—C2	1.447 (4)	C10—O2	1.244 (3)
C2—C3	1.352 (4)	C10—O1	1.250 (3)
C2—H2A	0.9300	N1—H1A	0.8600
C3—C4	1.433 (4)	O1W—H1	0.8501
C3—C10	1.514 (3)	O1W—H2	0.8500
C4—C9	1.405 (4)	O2W—H3	0.8500
C4—C5	1.414 (4)	O2W—H4	0.8499
C5—C6	1.371 (4)

O1ⁱ—Ni1—O1	180.0	C6—C5—H5A	119.7
O1ⁱ—Ni1—O1W	90.69 (10)	C4—C5—H5A	119.7
O1—Ni1—O1W	89.31 (10)	C5—C6—C7	120.4 (3)
O1ⁱ—Ni1—O1Wⁱ	89.31 (9)	C5—C6—H6A	119.8
O1—Ni1—O1Wⁱ	90.69 (10)	C7—C6—H6A	119.8
O1W—Ni1—O1Wⁱ	180.000 (1)	C8—C7—C6	120.8 (3)
O1ⁱ—Ni1—O2W	91.65 (8)	C8—C7—H7A	119.6
O1—Ni1—O2W	88.35 (8)	C6—C7—H7A	119.6
O1W—Ni1—O2W	89.05 (9)	C7—C8—C9	119.2 (3)
O1Wⁱ—Ni1—O2W	90.95 (9)	C7—C8—H8A	120.4
O1ⁱ—Ni1—O2Wⁱ	88.35 (8)	C9—C8—H8A	120.4
O1—Ni1—O2Wⁱ	91.65 (8)	N1—C9—C8	120.0 (2)
O1W—Ni1—O2Wⁱ	90.95 (9)	N1—C9—C4	119.1 (2)
O1Wⁱ—Ni1—O2Wⁱ	89.05 (9)	C8—C9—C4	120.9 (2)
O2W—Ni1—O2Wⁱ	180.00 (10)	O2—C10—O1	126.3 (2)
O3—C1—N1	120.0 (2)	O2—C10—C3	119.9 (2)
O3—C1—C2	123.8 (3)	O1—C10—C3	113.8 (2)
N1—C1—C2	116.2 (2)	C1—N1—C9	124.7 (2)
C3—C2—C1	121.4 (3)	C1—N1—H1A	117.6
C3—C2—H2A	119.3	C9—N1—H1A	117.6
C1—C2—H2A	119.3	C10—O1—Ni1	129.97 (18)
C2—C3—C4	120.6 (2)	Ni1—O1W—H1	123.7
C2—C3—C10	120.3 (2)	Ni1—O1W—H2	113.0
C4—C3—C10	119.0 (2)	H1—O1W—H2	109.1
C9—C4—C5	118.1 (3)	Ni1—O2W—H3	100.1
C9—C4—C3	117.9 (2)	Ni1—O2W—H4	118.4
C5—C4—C3	124.0 (2)	H3—O2W—H4	101.2
C6—C5—C4	120.6 (3)

O3—C1—C2—C3	179.5 (3)	C5—C4—C9—C8	−1.2 (4)
N1—C1—C2—C3	−0.8 (4)	C3—C4—C9—C8	178.9 (2)
C1—C2—C3—C4	2.3 (4)	C2—C3—C10—O2	−69.5 (4)
C1—C2—C3—C10	−175.4 (2)	C4—C3—C10—O2	112.8 (3)
C2—C3—C4—C9	−1.4 (4)	C2—C3—C10—O1	109.5 (3)
C10—C3—C4—C9	176.2 (2)	C4—C3—C10—O1	−68.2 (3)
C2—C3—C4—C5	178.6 (3)	O3—C1—N1—C9	178.1 (2)
C10—C3—C4—C5	−3.7 (4)	C2—C1—N1—C9	−1.7 (4)
C9—C4—C5—C6	1.3 (4)	C8—C9—N1—C1	−177.2 (3)
C3—C4—C5—C6	−178.7 (3)	C4—C9—N1—C1	2.5 (4)
C4—C5—C6—C7	−0.6 (5)	O2—C10—O1—Ni1	−4.1 (4)
C5—C6—C7—C8	−0.3 (5)	C3—C10—O1—Ni1	176.92 (17)
C6—C7—C8—C9	0.5 (4)	O1W—Ni1—O1—C10	115.2 (3)
C7—C8—C9—N1	−180.0 (2)	O1Wⁱ—Ni1—O1—C10	−64.8 (3)
C7—C8—C9—C4	0.3 (4)	O2W—Ni1—O1—C10	−155.7 (3)
C5—C4—C9—N1	179.1 (2)	O2Wⁱ—Ni1—O1—C10	24.3 (3)
C3—C4—C9—N1	−0.9 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2Wⁱⁱ	0.86	2.18	3.031 (3)	173
O1W—H1···O2ⁱⁱⁱ	0.85	1.94	2.783 (3)	169
O1W—H2···O3^iv	0.85	1.89	2.722 (3)	164
O2W—H3···O2ⁱ	0.85	1.90	2.709 (3)	158
O2W—H4···O3^v	0.85	1.98	2.767 (3)	154

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₆NO₃)₂(H₂O)₄]
M_r	507.07
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.105 (5), 8.507 (5), 9.216 (5)
α, β, γ (°)	108.723 (5), 108.396 (5), 90.840 (5)
V (Å³)	496.4 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.5 × 0.4 × 0.3

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.601, 0.721
No. of measured, independent and observed [I > 2σ(I)] reflections	3041, 2250, 2064
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.121, 1.02
No. of reflections	2250
No. of parameters	151
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.57

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Siemens, 1990).

Selected geometric parameters (Å, º) top

Ni1—O1	2.007 (2)	Ni1—O2W	2.117 (2)
Ni1—O1W	2.083 (2)

O1—Ni1—O1W	89.31 (10)	O1W—Ni1—O2W	89.05 (9)
O1—Ni1—O1Wⁱ	90.69 (10)	O1Wⁱ—Ni1—O2W	90.95 (9)
O1—Ni1—O2W	88.35 (8)	O1—Ni1—O2Wⁱ	91.65 (8)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2Wⁱⁱ	0.86	2.18	3.031 (3)	173.2
O1W—H1···O2ⁱⁱⁱ	0.85	1.94	2.783 (3)	169.4
O1W—H2···O3^iv	0.85	1.89	2.722 (3)	164.0
O2W—H3···O2ⁱ	0.85	1.90	2.709 (3)	158.3
O2W—H4···O3^v	0.85	1.98	2.767 (3)	153.9

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

Acknowledgements

We thank the Changjiang Scholars and Innovative Research Team in Universities Program, the National Natural Science Foundation of China (grant No. 20573016) and the Science Foundation for Young Teachers of Northeast Normal University (grant No. 20070310) for financial support.

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