Tetra­aqua­bis[3-(4-pyrid­yl)benzoato-κN]nickel(II)

Wang, Q.-X.; Zeng, M.-H.; Ng, S.W.

doi:10.1107/S1600536809051204

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1708

doi:10.1107/S1600536809051204

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Tetraaquabis[3-(4-pyridyl)benzoato-κN]nickel(II)

Qiang-Xin Wang,^a Ming-Hua Zeng ^a and Seik Weng Ng ^b ^*

^aSchool of Chemistry & Chemical Engineering, Guangxi Normal University, 541004 Guilin 541004, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 November 2009; accepted 27 November 2009; online 28 November 2009)

The Ni^II atom in the title compound, [Ni(C₁₂H₈NO₂)₂(H₂O)₄], exists in an all-trans octahedral coordination environment. The 3-(4-pyridyl)benzoate ligand binds to Ni atom through the pyridyl N atom; the pyridine and benzene rings are oriented at a dihedral angle of 26.27 (10)°. Adjacent complexes are linked by O—H⋯O hydrogen bonds, forming a three-dimensional network. The metal atom lies on a special position of 2 site symmetry in the crystal structure.

Related literature

The 3-(pyridin-4-yl)benzoate unit is fairly rigid like the nicotinate unit, which also forms a similar zwitterionic nickel derivative; see: Batten & Harris (2001 ).

Experimental

Crystal data

[Ni(C₁₂H₈NO₂)₂(H₂O)₄]
M_r = 527.16
Monoclinic, C 2/c
a = 24.564 (3) Å
b = 7.0520 (8) Å
c = 13.781 (2) Å
β = 113.325 (2)°
V = 2192.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 173 K
0.47 × 0.31 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.666, T_max = 0.929
5587 measured reflections
2360 independent reflections
1977 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.090
S = 1.09
2360 reflections
175 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1W	2.0627 (14)
Ni1—O2W	2.0811 (14)
Ni1—N1	2.0931 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O1ⁱ	0.84 (1)	1.88 (1)	2.682 (2)	160 (3)
O1w—H12⋯O2ⁱⁱ	0.83 (1)	1.91 (1)	2.734 (2)	170 (2)
O2w—H21⋯O1ⁱⁱⁱ	0.84 (1)	1.93 (1)	2.732 (2)	159 (2)
O2w—H22⋯O2^iv	0.83 (1)	1.88 (1)	2.711 (2)	177 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iv) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051204/xu2699sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051204/xu2699Isup2.hkl

checkCIF report

Related literature top

The 3-(pyridin-4-yl)benzoate unit is fairly rigid like the nicotinate unit, which also forms a similar zwitterionic nickel derivative; see: Batten & Harris (2001).

Experimental top

3-(Pyridin-4-yl)benzoic acid was purchased from a chemical supplier. The reagent (0.199 g, 1 mmol) and sodium hydroxide (0.040 g, 1 mmol) were mixed with nickel(II) nitrate hexahydrate (0.150 g, 0.5 mmol) in water (10 ml). The mixture was placed in a 15 ml Teflon-lined autoclave and heated at 423 K for 48 h. The autoclave was cooled over 12 h at a rate of 5 K an hour. Green crystals were isolated by hand (yield ca 60% based on Ni).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ni(H₂O)₄(C₁₂H₂NO₂)₂ at the 70% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.

Tetraaquabis[3-(4-pyridyl)benzoato-κN]nickel(II) top

Crystal data top

[Ni(C₁₂H₈NO₂)₂(H₂O)₄]	F(000) = 1096
M_r = 527.16	D_x = 1.597 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 996 reflections
a = 24.564 (3) Å	θ = 3.0–26.9°
b = 7.0520 (8) Å	µ = 0.94 mm⁻¹
c = 13.781 (2) Å	T = 173 K
β = 113.325 (2)°	Prism, green
V = 2192.1 (4) Å³	0.47 × 0.31 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	1977 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→31
T_min = 0.666, T_max = 0.929	k = −8→8
5587 measured reflections	l = −17→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0539P)² + 0.5684P] where P = (F_o² + 2F_c²)/3
2360 reflections	(Δ/σ)_max = 0.001
175 parameters	Δρ_max = 0.38 e Å⁻³
4 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Ni(C₁₂H₈NO₂)₂(H₂O)₄]	V = 2192.1 (4) Å³
M_r = 527.16	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.564 (3) Å	µ = 0.94 mm⁻¹
b = 7.0520 (8) Å	T = 173 K
c = 13.781 (2) Å	0.47 × 0.31 × 0.08 mm
β = 113.325 (2)°

Data collection top

Bruker APEXII diffractometer	2360 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1977 reflections with I > 2σ(I)
T_min = 0.666, T_max = 0.929	R_int = 0.023
5587 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	4 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.38 e Å⁻³
2360 reflections	Δρ_min = −0.27 e Å⁻³
175 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.30069 (5)	0.7500	0.01561 (13)
N1	0.58142 (7)	0.3092 (2)	0.73473 (13)	0.0179 (3)
O1	0.90563 (6)	0.2232 (2)	0.96391 (12)	0.0266 (3)
O2	0.96160 (6)	0.29413 (19)	0.87580 (12)	0.0242 (3)
O1W	0.46891 (6)	0.0848 (2)	0.64084 (11)	0.0199 (3)
O2W	0.53247 (6)	0.5047 (2)	0.86819 (11)	0.0208 (3)
C1	0.91223 (9)	0.2740 (3)	0.88189 (16)	0.0197 (4)
C2	0.85662 (8)	0.3156 (3)	0.78537 (16)	0.0172 (4)
C3	0.85969 (8)	0.3652 (3)	0.69003 (17)	0.0208 (4)
H3	0.8970	0.3732	0.6845	0.025*
C4	0.80768 (8)	0.4029 (3)	0.60302 (16)	0.0220 (4)
H4	0.8096	0.4366	0.5377	0.026*
C5	0.75295 (8)	0.3919 (3)	0.61016 (15)	0.0205 (4)
H5	0.7178	0.4188	0.5500	0.025*
C6	0.74932 (8)	0.3414 (3)	0.70535 (15)	0.0176 (4)
C7	0.80178 (8)	0.3043 (3)	0.79252 (16)	0.0173 (4)
H7	0.8000	0.2706	0.8580	0.021*
C8	0.69121 (8)	0.3288 (3)	0.71474 (16)	0.0173 (4)
C9	0.68658 (8)	0.3575 (3)	0.81138 (16)	0.0198 (4)
H9	0.7210	0.3856	0.8727	0.024*
C10	0.63215 (9)	0.3452 (3)	0.81801 (16)	0.0205 (4)
H10	0.6305	0.3632	0.8851	0.025*
C11	0.58576 (9)	0.2824 (3)	0.64134 (16)	0.0199 (4)
H11A	0.5505	0.2566	0.5811	0.024*
C12	0.63867 (8)	0.2903 (3)	0.62852 (16)	0.0198 (4)
H12A	0.6392	0.2694	0.5608	0.024*
H11	0.4524 (11)	0.124 (4)	0.5786 (11)	0.048 (9)*
H12	0.4935 (8)	0.004 (3)	0.6396 (17)	0.023 (6)*
H21	0.5473 (10)	0.452 (3)	0.9275 (11)	0.030 (7)*
H22	0.5096 (10)	0.591 (3)	0.869 (2)	0.043 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01032 (18)	0.0186 (2)	0.0183 (2)	0.000	0.00608 (14)	0.000
N1	0.0125 (7)	0.0184 (8)	0.0222 (9)	−0.0001 (6)	0.0061 (7)	0.0022 (7)
O1	0.0189 (7)	0.0361 (9)	0.0215 (8)	−0.0012 (6)	0.0043 (6)	0.0023 (6)
O2	0.0118 (7)	0.0227 (8)	0.0362 (9)	0.0008 (5)	0.0077 (6)	0.0012 (6)
O1W	0.0155 (7)	0.0222 (8)	0.0216 (8)	0.0010 (6)	0.0071 (6)	−0.0019 (6)
O2W	0.0156 (7)	0.0225 (8)	0.0226 (8)	0.0028 (6)	0.0056 (6)	−0.0022 (6)
C1	0.0154 (9)	0.0154 (9)	0.0259 (11)	−0.0002 (7)	0.0056 (8)	−0.0042 (8)
C2	0.0149 (9)	0.0145 (9)	0.0214 (10)	−0.0026 (7)	0.0064 (8)	−0.0045 (8)
C3	0.0149 (9)	0.0215 (10)	0.0294 (11)	−0.0027 (8)	0.0122 (8)	−0.0026 (8)
C4	0.0212 (10)	0.0277 (11)	0.0202 (10)	−0.0032 (8)	0.0115 (8)	−0.0003 (9)
C5	0.0158 (9)	0.0234 (10)	0.0206 (10)	−0.0007 (8)	0.0054 (8)	−0.0002 (8)
C6	0.0135 (9)	0.0176 (9)	0.0223 (10)	−0.0020 (7)	0.0078 (8)	−0.0033 (7)
C7	0.0156 (9)	0.0179 (9)	0.0187 (9)	0.0002 (7)	0.0071 (8)	0.0002 (8)
C8	0.0149 (9)	0.0163 (9)	0.0205 (10)	0.0014 (7)	0.0069 (8)	0.0024 (7)
C9	0.0130 (9)	0.0242 (10)	0.0204 (10)	0.0011 (8)	0.0047 (8)	0.0004 (8)
C10	0.0175 (9)	0.0255 (10)	0.0198 (10)	0.0014 (8)	0.0090 (8)	0.0003 (8)
C11	0.0139 (9)	0.0237 (10)	0.0210 (10)	−0.0004 (8)	0.0057 (8)	0.0008 (8)
C12	0.0167 (10)	0.0230 (10)	0.0196 (10)	−0.0007 (8)	0.0071 (8)	−0.0007 (8)

Geometric parameters (Å, º) top

Ni1—O1W	2.0627 (14)	C3—C4	1.388 (3)
Ni1—O1Wⁱ	2.0627 (14)	C3—H3	0.9500
Ni1—O2W	2.0811 (14)	C4—C5	1.389 (3)
Ni1—O2Wⁱ	2.0811 (14)	C4—H4	0.9500
Ni1—N1ⁱ	2.0931 (16)	C5—C6	1.396 (3)
Ni1—N1	2.0931 (16)	C5—H5	0.9500
N1—C10	1.342 (3)	C6—C7	1.395 (3)
N1—C11	1.346 (2)	C6—C8	1.486 (3)
O1—C1	1.256 (3)	C7—H7	0.9500
O2—C1	1.256 (2)	C8—C12	1.392 (3)
O1W—H11	0.838 (10)	C8—C9	1.396 (3)
O1W—H12	0.834 (10)	C9—C10	1.378 (3)
O2W—H21	0.840 (10)	C9—H9	0.9500
O2W—H22	0.833 (10)	C10—H10	0.9500
C1—C2	1.511 (3)	C11—C12	1.380 (3)
C2—C3	1.390 (3)	C11—H11A	0.9500
C2—C7	1.391 (3)	C12—H12A	0.9500

O1W—Ni1—O1Wⁱ	84.85 (8)	C4—C3—C2	119.26 (17)
O1W—Ni1—O2W	176.09 (6)	C4—C3—H3	120.4
O1Wⁱ—Ni1—O2W	91.32 (6)	C2—C3—H3	120.4
O1W—Ni1—O2Wⁱ	91.32 (6)	C3—C4—C5	120.92 (18)
O1Wⁱ—Ni1—O2Wⁱ	176.09 (6)	C3—C4—H4	119.5
O2W—Ni1—O2Wⁱ	92.51 (8)	C5—C4—H4	119.5
O1W—Ni1—N1ⁱ	90.11 (6)	C4—C5—C6	120.31 (18)
O1Wⁱ—Ni1—N1ⁱ	92.32 (6)	C4—C5—H5	119.8
O2W—Ni1—N1ⁱ	89.24 (6)	C6—C5—H5	119.8
O2Wⁱ—Ni1—N1ⁱ	88.48 (6)	C7—C6—C5	118.45 (17)
O1W—Ni1—N1	92.32 (6)	C7—C6—C8	120.35 (17)
O1Wⁱ—Ni1—N1	90.11 (6)	C5—C6—C8	121.19 (17)
O2W—Ni1—N1	88.48 (6)	C2—C7—C6	121.21 (18)
O2Wⁱ—Ni1—N1	89.24 (6)	C2—C7—H7	119.4
N1ⁱ—Ni1—N1	176.71 (9)	C6—C7—H7	119.4
C10—N1—C11	116.48 (16)	C12—C8—C9	116.40 (17)
C10—N1—Ni1	121.33 (13)	C12—C8—C6	122.37 (18)
C11—N1—Ni1	122.18 (13)	C9—C8—C6	121.23 (17)
Ni1—O1W—H11	113 (2)	C10—C9—C8	120.12 (18)
Ni1—O1W—H12	117.0 (16)	C10—C9—H9	119.9
H11—O1W—H12	105 (2)	C8—C9—H9	119.9
Ni1—O2W—H21	109.7 (18)	N1—C10—C9	123.49 (18)
Ni1—O2W—H22	117.8 (19)	N1—C10—H10	118.3
H21—O2W—H22	110 (2)	C9—C10—H10	118.3
O1—C1—O2	124.36 (19)	N1—C11—C12	123.49 (19)
O1—C1—C2	116.99 (17)	N1—C11—H11A	118.3
O2—C1—C2	118.65 (18)	C12—C11—H11A	118.3
C3—C2—C7	119.85 (18)	C11—C12—C8	120.03 (19)
C3—C2—C1	120.82 (17)	C11—C12—H12A	120.0
C7—C2—C1	119.32 (18)	C8—C12—H12A	120.0

O1W—Ni1—N1—C10	−144.22 (15)	C3—C2—C7—C6	0.1 (3)
O1Wⁱ—Ni1—N1—C10	−59.36 (15)	C1—C2—C7—C6	−179.93 (17)
O2W—Ni1—N1—C10	31.96 (15)	C5—C6—C7—C2	−0.4 (3)
O2Wⁱ—Ni1—N1—C10	124.49 (15)	C8—C6—C7—C2	−179.88 (17)
O1W—Ni1—N1—C11	36.93 (15)	C7—C6—C8—C12	−154.18 (19)
O1Wⁱ—Ni1—N1—C11	121.79 (15)	C5—C6—C8—C12	26.4 (3)
O2W—Ni1—N1—C11	−146.89 (15)	C7—C6—C8—C9	26.6 (3)
O2Wⁱ—Ni1—N1—C11	−54.36 (15)	C5—C6—C8—C9	−152.89 (19)
O1—C1—C2—C3	−177.38 (18)	C12—C8—C9—C10	0.6 (3)
O2—C1—C2—C3	3.5 (3)	C6—C8—C9—C10	179.95 (18)
O1—C1—C2—C7	2.7 (3)	C11—N1—C10—C9	0.8 (3)
O2—C1—C2—C7	−176.42 (17)	Ni1—N1—C10—C9	−178.14 (15)
C7—C2—C3—C4	0.0 (3)	C8—C9—C10—N1	−1.1 (3)
C1—C2—C3—C4	−179.89 (18)	C10—N1—C11—C12	0.0 (3)
C2—C3—C4—C5	0.1 (3)	Ni1—N1—C11—C12	178.89 (14)
C3—C4—C5—C6	−0.4 (3)	N1—C11—C12—C8	−0.4 (3)
C4—C5—C6—C7	0.5 (3)	C9—C8—C12—C11	0.1 (3)
C4—C5—C6—C8	179.99 (18)	C6—C8—C12—C11	−179.22 (18)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O1ⁱⁱ	0.84 (1)	1.88 (1)	2.682 (2)	160 (3)
O1w—H12···O2ⁱⁱⁱ	0.83 (1)	1.91 (1)	2.734 (2)	170 (2)
O2w—H21···O1^iv	0.84 (1)	1.93 (1)	2.732 (2)	159 (2)
O2w—H22···O2^v	0.83 (1)	1.88 (1)	2.711 (2)	177 (3)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₈NO₂)₂(H₂O)₄]
M_r	527.16
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	24.564 (3), 7.0520 (8), 13.781 (2)
β (°)	113.325 (2)
V (Å³)	2192.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.47 × 0.31 × 0.08

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.666, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	5587, 2360, 1977
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.090, 1.09
No. of reflections	2360
No. of parameters	175
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Ni1—O1W	2.0627 (14)	Ni1—N1	2.0931 (16)
Ni1—O2W	2.0811 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O1ⁱ	0.84 (1)	1.88 (1)	2.682 (2)	160 (3)
O1w—H12···O2ⁱⁱ	0.83 (1)	1.91 (1)	2.734 (2)	170 (2)
O2w—H21···O1ⁱⁱⁱ	0.84 (1)	1.93 (1)	2.732 (2)	159 (2)
O2w—H22···O2^iv	0.83 (1)	1.88 (1)	2.711 (2)	177 (3)

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

Acknowledgements

This work was supported by the Guangxi Graduate Education Innovation Program (2009106020703M44) and the University of Malaya.

References

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