The crystal structure of a new polymorph of hexa­aqua­nickel(II) bis­(6-oxo-1,6-di­hydro­pyridine-3-carboxyl­ate)

Pérez-Aguirre, R.; Pérez-Yáñez, S.; Beobide, G.; Castillo, O.; Gutiérrez-Zorrilla, J.M.; Luque, A.

doi:10.1107/S2056989015022422

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages m238-m239

https://doi.org/10.1107/S2056989015022422

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The crystal structure of a new polymorph of hexaaquanickel(II) bis(6-oxo-1,6-dihydropyridine-3-carboxylate)

Rubén Pérez-Aguirre,^a Sonia Pérez-Yáñez,^a Garikoitz Beobide,^a Oscar Castillo,^a ^* Juan Manuel Gutiérrez-Zorrilla ^a and Antonio Luque ^a

^aDepartamento de Química Inorgánica., Facultad de Ciencia y Tecnología, Universidad del País Vasco, UPV/EHU, Apdo. 644, E-48080 Bilbao, Spain
^*Correspondence e-mail: oscar.castillo@ehu.eus

Edited by M. Weil, Vienna University of Technology, Austria (Received 16 November 2015; accepted 24 November 2015; online 28 November 2015)

In a new polymorph of the title salt, [Ni(H₂O)₆](C₆H₄NO₃)₂, the metal atom of the cationic complex lies on a symmetry centre and is coordinated by six water molecules to provide a quite regular octahedral coordination environment. These cations interact with 6-oxo-1,6-dihydropyridine-3-carboxylate anions through electrostatic interactions and by means of O—H⋯O and N—H⋯O hydrogen bonds involving the carboxylate, keto and protonated imine groups of the anion, and the coordinating water molecules from the cationic complex entity to generate a supramolecular three-dimensional architecture. The previously reported polymorph of this compound presents a network of hydrogen bonds, in which the organic anions establish mutual hydrogen-bonding interactions involving their keto and protonated imine groups.

Keywords: crystal structure; polymorph; 6-oxo-1,6-dihydropyridine-3-carboxylate anion; hydrogen bonding,.

CCDC reference: 1438522

1. Related literature

The zinc and cobalt analogues (Zhang et al., 2005 ; Song et al., 2005 ; Zhang & Ng, 2005a ) of the title salt are isostructural with the previously reported polymorph of [Ni(H₂O)₆](C₆H₄NO₃)₂ (Zhang & Ng, 2005b ). It is worth mentioning that although the authors claimed a lactim tautomer of the organic anion to be present in all these structures, the C—O bond length seems to indicate of a lactam tautomer as in the case of the title compound. For additional examples of coordination complexes with 6-oxo-1,6-dihydropyridine-3-carboxylate anions and copper(II), see: Zeng et al. (2007 ).

2. Experimental

2.1. Crystal data

[Ni(H₂O)₆](C₆H₄NO₃)₂
M_r = 443.01
Triclinic, $[P \overline 1]$
a = 6.2620 (5) Å
b = 7.1053 (7) Å
c = 10.7101 (10) Å
α = 102.461 (8)°
β = 96.754 (7)°
γ = 114.823 (8)°
V = 410.49 (7) Å³
Z = 1
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 100 K
0.08 × 0.07 × 0.06 mm

2.2. Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.888, T_max = 0.936
2781 measured reflections
1801 independent reflections
1654 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.070
S = 1.06
1801 reflections
146 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1W	2.0184 (16)
Ni1—O3W	2.0242 (16)
Ni1—O2W	2.0990 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2W	0.87 (2)	2.06 (3)	2.906 (2)	167 (2)
O1W—H11W⋯O71ⁱ	0.77 (3)	1.85 (3)	2.612 (2)	173 (3)
O1W—H12W⋯O72ⁱⁱ	0.78 (3)	1.97 (3)	2.748 (2)	173 (3)
O2W—H21W⋯O2ⁱⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	173 (2)
O2W—H22W⋯O2^iv	0.77 (3)	1.98 (3)	2.743 (2)	169 (3)
O3W—H31W⋯O72ⁱ	0.74 (3)	1.92 (3)	2.660 (2)	174 (3)
O3W—H32W⋯O2^v	0.81 (3)	2.01 (3)	2.813 (2)	172 (3)
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+2, -y, -z+2; (iii) -x+1, -y-1, -z+1; (iv) x-1, y, z; (v) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1438522

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015022422/wm5241sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022422/wm5241Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015022422/wm5241Isup3.cdx

checkCIF report

Related literature top

The zinc and cobalt analogues (Zhang et al., 2005; Song et al., 2005; Zhang & Ng, 2005a) of the title salt are isostructural with the previously reported polymorph of [Ni(H₂O)₆](C₆H₄NO₃)₂ (Zhang & Ng, 2005b). It is worth mentioning that although the authors claimed a lactim tautomer of the organic anion to be present in all these structures, the C—O bond length seems to indicate of a lactam tautomer as in the case of the title compound. For additional examples of coordination complexes with 6-oxo-1,6-dihydropyridine-3-carboxylate anions and copper(II), see: Zeng et al. (2007).

Experimental top

6-Oxo-1,6-dihydropyridine-3-carboxylic acid (0.8 mmol) and Ni(NO₃)₂·6H₂O (0.4 mmol) were dissolved in 40 ml of distilled water. After stirring for half an hour, the solution was left evaporating at room temperature. Two weeks later light green crystals of the title compound were obtained.

Structure description top

The zinc and cobalt analogues (Zhang et al., 2005; Song et al., 2005; Zhang & Ng, 2005a) of the title salt are isostructural with the previously reported polymorph of [Ni(H₂O)₆](C₆H₄NO₃)₂ (Zhang & Ng, 2005b). It is worth mentioning that although the authors claimed a lactim tautomer of the organic anion to be present in all these structures, the C—O bond length seems to indicate of a lactam tautomer as in the case of the title compound. For additional examples of coordination complexes with 6-oxo-1,6-dihydropyridine-3-carboxylate anions and copper(II), see: Zeng et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The structures of the molecular entities in (I), drawn with displacement ellipsoids at the 50% probability level. [Symmetry code: -x+1, -y, -z+1.]
	Fig. 2. Hydrogen-bonding interactions (dashed lines) taking place between the [Ni(H₂O)₆]²⁺ complex cations and the 6-oxo-1,6-dihydropyridine-3-carboxylate anions.

Hexaaquanickel(II) bis(6-oxo-1,6-dihydropyridine-3-carboxylate) top

Crystal data top

[Ni(H₂O)₆](C₆H₄NO₃)₂	Z = 1
M_r = 443.01	F(000) = 230
Triclinic, P1	D_x = 1.792 Mg m⁻³
a = 6.2620 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.1053 (7) Å	Cell parameters from 2781 reflections
c = 10.7101 (10) Å	θ = 2.0–28.2°
α = 102.461 (8)°	µ = 1.26 mm⁻¹
β = 96.754 (7)°	T = 100 K
γ = 114.823 (8)°	Block, light green
V = 410.49 (7) Å³	0.08 × 0.07 × 0.06 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	1801 independent reflections
Radiation source: sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 8.192 pixels mm^-1	θ_max = 28.2°, θ_min = 2.0°
thin–slice ω scans	h = −5→8
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	k = −9→5
T_min = 0.888, T_max = 0.936	l = −14→13
2781 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)] = 0.032	Hydrogen site location: mixed
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0191P)² + 0.3293P] where P = (F_o² + 2F_c²)/3
1801 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ni(H₂O)₆](C₆H₄NO₃)₂	γ = 114.823 (8)°
M_r = 443.01	V = 410.49 (7) Å³
Triclinic, P1	Z = 1
a = 6.2620 (5) Å	Mo Kα radiation
b = 7.1053 (7) Å	µ = 1.26 mm⁻¹
c = 10.7101 (10) Å	T = 100 K
α = 102.461 (8)°	0.08 × 0.07 × 0.06 mm
β = 96.754 (7)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	1801 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	1654 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.936	R_int = 0.020
2781 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.45 e Å⁻³
1801 reflections	Δρ_min = −0.39 e Å⁻³
146 parameters

Special details top

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 > 2sigma(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	0.5000	0.0000	0.5000	0.01281 (12)
O1W	0.7185 (3)	0.1609 (3)	0.68193 (15)	0.0168 (3)
O71	0.5271 (3)	−0.1565 (3)	1.13681 (15)	0.0202 (4)
O2W	0.3038 (3)	−0.2654 (3)	0.56622 (15)	0.0154 (3)
O3W	0.2933 (3)	0.1461 (3)	0.55076 (17)	0.0231 (4)
O2	0.8636 (3)	−0.3362 (3)	0.62046 (14)	0.0176 (3)
O72	0.8231 (3)	−0.2245 (3)	1.21937 (15)	0.0202 (4)
N1	0.6616 (3)	−0.2558 (3)	0.76999 (18)	0.0162 (4)
C2	0.8355 (4)	−0.3128 (4)	0.7379 (2)	0.0141 (4)
C4	0.9331 (4)	−0.3021 (3)	0.9661 (2)	0.0140 (4)
H4	1.0278	−0.3170	1.0333	0.017*
C3	0.9726 (4)	−0.3378 (4)	0.8423 (2)	0.0148 (4)
H3	1.0917	−0.3793	0.8264	0.018*
C5	0.7512 (4)	−0.2432 (3)	0.9937 (2)	0.0130 (4)
C7	0.6965 (4)	−0.2048 (3)	1.1271 (2)	0.0144 (4)
C6	0.6196 (4)	−0.2203 (4)	0.8921 (2)	0.0154 (4)
H6	0.4995	−0.1797	0.9070	0.018*
H1	0.574 (4)	−0.240 (4)	0.708 (3)	0.018*
H31W	0.266 (5)	0.177 (4)	0.615 (3)	0.023*
H21W	0.262 (5)	−0.387 (5)	0.505 (3)	0.023*
H22W	0.189 (5)	−0.270 (4)	0.588 (3)	0.023*
H11W	0.650 (5)	0.171 (4)	0.736 (3)	0.023*
H12W	0.844 (5)	0.170 (4)	0.712 (3)	0.023*
H32W	0.236 (5)	0.196 (5)	0.503 (3)	0.038 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0108 (2)	0.0231 (2)	0.0093 (2)	0.01104 (17)	0.00397 (15)	0.00593 (16)
O1W	0.0119 (8)	0.0321 (10)	0.0095 (8)	0.0130 (7)	0.0037 (6)	0.0053 (7)
O71	0.0201 (8)	0.0353 (10)	0.0169 (8)	0.0204 (8)	0.0102 (7)	0.0109 (7)
O2W	0.0127 (8)	0.0239 (9)	0.0126 (8)	0.0102 (7)	0.0056 (6)	0.0058 (7)
O3W	0.0303 (10)	0.0467 (12)	0.0121 (8)	0.0320 (9)	0.0110 (7)	0.0135 (8)
O2	0.0198 (8)	0.0248 (9)	0.0126 (8)	0.0127 (7)	0.0073 (6)	0.0067 (7)
O72	0.0180 (8)	0.0384 (10)	0.0112 (8)	0.0187 (8)	0.0048 (6)	0.0079 (7)
N1	0.0152 (9)	0.0275 (11)	0.0121 (9)	0.0135 (8)	0.0047 (8)	0.0094 (8)
C2	0.0133 (10)	0.0176 (11)	0.0130 (10)	0.0074 (9)	0.0061 (8)	0.0054 (9)
C4	0.0132 (10)	0.0156 (11)	0.0138 (10)	0.0084 (9)	0.0010 (8)	0.0033 (9)
C3	0.0118 (10)	0.0190 (11)	0.0170 (11)	0.0102 (9)	0.0053 (8)	0.0042 (9)
C5	0.0113 (10)	0.0159 (11)	0.0115 (10)	0.0058 (8)	0.0038 (8)	0.0038 (8)
C7	0.0127 (10)	0.0169 (11)	0.0133 (11)	0.0062 (9)	0.0039 (8)	0.0047 (9)
C6	0.0130 (10)	0.0233 (12)	0.0145 (11)	0.0107 (9)	0.0066 (9)	0.0075 (9)

Geometric parameters (Å, º) top

Ni1—O1W	2.0184 (16)	O2—C2	1.275 (2)
Ni1—O1Wⁱ	2.0184 (16)	O72—C7	1.262 (3)
Ni1—O3Wⁱ	2.0242 (16)	N1—C6	1.356 (3)
Ni1—O3W	2.0242 (16)	N1—C2	1.366 (3)
Ni1—O2Wⁱ	2.0990 (16)	N1—H1	0.87 (2)
Ni1—O2W	2.0990 (16)	C2—C3	1.417 (3)
O1W—H11W	0.77 (3)	C4—C3	1.367 (3)
O1W—H12W	0.78 (3)	C4—C5	1.409 (3)
O71—C7	1.253 (2)	C4—H4	0.9300
O2W—H21W	0.88 (3)	C3—H3	0.9300
O2W—H22W	0.77 (3)	C5—C6	1.366 (3)
O3W—H31W	0.74 (3)	C5—C7	1.503 (3)
O3W—H32W	0.81 (3)	C6—H6	0.9300

O1W—Ni1—O1Wⁱ	180.0	H31W—O3W—H32W	106 (3)
O1W—Ni1—O2W	89.95 (6)	C6—N1—C2	124.28 (18)
O1W—Ni1—O2Wⁱ	90.05 (6)	C6—N1—H1	118.1 (16)
O1W—Ni1—O3W	88.06 (7)	C2—N1—H1	117.6 (16)
O1W—Ni1—O3Wⁱ	91.94 (7)	O2—C2—N1	118.94 (19)
O2W—Ni1—O3W	92.99 (7)	O2—C2—C3	125.81 (19)
O2W—Ni1—O3Wⁱ	87.01 (7)	N1—C2—C3	115.24 (18)
O1Wⁱ—Ni1—O3Wⁱ	88.06 (7)	C3—C4—C5	121.08 (19)
O1Wⁱ—Ni1—O3W	91.94 (7)	C3—C4—H4	119.5
O3Wⁱ—Ni1—O3W	180.0	C5—C4—H4	119.5
O1Wⁱ—Ni1—O2Wⁱ	89.95 (6)	C4—C3—C2	121.22 (19)
O3Wⁱ—Ni1—O2Wⁱ	92.99 (7)	C4—C3—H3	119.4
O1Wⁱ—Ni1—O2W	90.05 (6)	C2—C3—H3	119.4
O3Wⁱ—Ni1—O2W	87.01 (7)	C6—C5—C4	117.18 (19)
O2Wⁱ—Ni1—O2W	180.0	C6—C5—C7	119.20 (18)
Ni1—O1W—H11W	114 (2)	C4—C5—C7	123.62 (18)
Ni1—O1W—H12W	130 (2)	O71—C7—O72	125.51 (19)
H11W—O1W—H12W	110 (3)	O71—C7—C5	116.72 (18)
Ni1—O2W—H21W	110.1 (17)	O72—C7—C5	117.77 (18)
Ni1—O2W—H22W	116 (2)	N1—C6—C5	120.98 (19)
H21W—O2W—H22W	108 (3)	N1—C6—H6	119.5
Ni1—O3W—H31W	129 (2)	C5—C6—H6	119.5
Ni1—O3W—H32W	124 (2)

C6—N1—C2—O2	−178.1 (2)	C6—C5—C7—O71	1.2 (3)
C6—N1—C2—C3	1.1 (3)	C4—C5—C7—O71	−178.9 (2)
C5—C4—C3—C2	1.2 (3)	C6—C5—C7—O72	−179.1 (2)
O2—C2—C3—C4	177.9 (2)	C4—C5—C7—O72	0.8 (3)
N1—C2—C3—C4	−1.2 (3)	C2—N1—C6—C5	−1.0 (3)
C3—C4—C5—C6	−1.0 (3)	C4—C5—C6—N1	0.8 (3)
C3—C4—C5—C7	179.1 (2)	C7—C5—C6—N1	−179.3 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2W	0.87 (2)	2.06 (3)	2.906 (2)	167 (2)
O1W—H11W···O71ⁱⁱ	0.77 (3)	1.85 (3)	2.612 (2)	173 (3)
O1W—H12W···O72ⁱⁱⁱ	0.78 (3)	1.97 (3)	2.748 (2)	173 (3)
O2W—H21W···O2^iv	0.88 (3)	1.90 (3)	2.772 (2)	173 (2)
O2W—H22W···O2^v	0.77 (3)	1.98 (3)	2.743 (2)	169 (3)
O3W—H31W···O72ⁱⁱ	0.74 (3)	1.92 (3)	2.660 (2)	174 (3)
O3W—H32W···O2ⁱ	0.81 (3)	2.01 (3)	2.813 (2)	172 (3)

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

Selected bond lengths (Å) top

Ni1—O1W	2.0184 (16)	Ni1—O2W	2.0990 (16)
Ni1—O3W	2.0242 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2W	0.87 (2)	2.06 (3)	2.906 (2)	167 (2)
O1W—H11W···O71ⁱ	0.77 (3)	1.85 (3)	2.612 (2)	173 (3)
O1W—H12W···O72ⁱⁱ	0.78 (3)	1.97 (3)	2.748 (2)	173 (3)
O2W—H21W···O2ⁱⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	173 (2)
O2W—H22W···O2^iv	0.77 (3)	1.98 (3)	2.743 (2)	169 (3)
O3W—H31W···O72ⁱ	0.74 (3)	1.92 (3)	2.660 (2)	174 (3)
O3W—H32W···O2^v	0.81 (3)	2.01 (3)	2.813 (2)	172 (3)

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

Acknowledgements

This work has been funded by Eusko Jaurlaritza/Gobierno Vasco (Grant IT477–10), Universidad del País Vasco/Euskal Herriko Unibertsitatea (EHUA14/09, Grant UFI11/53), and the Ministerio de Economía y Competitividad (MAT2013–46502-C2–1-P). The authors are thankful for technical and human support provided by S. GIker of UPV/EHU.

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages m238-m239

https://doi.org/10.1107/S2056989015022422

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

The crystal structure of a new polymorph of hexa­aqua­nickel(II) bis­­(6-oxo-1,6-di­hydro­pyridine-3-carboxyl­ate)

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

The crystal structure of a new polymorph of hexaaquanickel(II) bis(6-oxo-1,6-dihydropyridine-3-carboxylate)