Poly[aqua­[μ3-4-carb­oxy-2-(pyridin-4-yl)-1H-imidazole-5-carboxyl­ato-κ5N1,O5:N3,O4:N2]nickel(II)]

Jing, X.-M.; Gong, S.; Xiao, L.-W.

doi:10.1107/S1600536812001900

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m187

doi:10.1107/S1600536812001900

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Poly[aqua[μ₃-4-carboxy-2-(pyridin-4-yl)-1H-imidazole-5-carboxylato-κ⁵N¹,O⁵:N³,O⁴:N²]nickel(II)]

Xue-Min Jing,^a ^* Shu-zhe Gong ^b and Li-Wei Xiao ^a

^aFaculty of Chemistry and Material Science, Langfang Teachers College, Langfang, Hebei 065000, People's Republic of China, and ^bKey Laboratory of Oilfield Applied Chemistry, College of Heilongjiang Province, Chemistry & Chemical Engineering Daqing Normal University, Daqing, Heilongjiang 163712, People's Republic of China
^*Correspondence e-mail: jingxm1982@gmail.com

(Received 15 December 2011; accepted 16 January 2012; online 21 January 2012)

The water-coordinated Ni²⁺ cation in the title compound, [Ni(C₁₀H₅N₃O₄)(H₂O)]_n, assumes an octahedral NiN₃O₃ coordination mode and is N,O-chelated by two deprotonated 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acid (HPyImDC²⁻) ligands, forming a layer structure extending in the bc plane. The chains are arranged along the b-axis direction, forming a layer structure extending in the bc plane. O—H⋯O hydrogen bonding between the layers results in the formation of a three-dimensional supramolecular framework. The structure is isotypic with the Zn analogue [Li et al. (2009). Cryst. Growth Des. 6, 3423–3431].

Related literature

For the isotypic Zn compound, see: Li et al. (2009 ). The HPyImDC²⁻ anion behaves as a T-shaped linker, see: Jing et al. (2010 ).

Experimental

Crystal data

[Ni(C₁₀H₅N₃O₄)(H₂O)]
M_r = 307.88
Monoclinic, P 2₁ /c
a = 7.5117 (15) Å
b = 11.400 (2) Å
c = 12.896 (4) Å
β = 109.04 (3)°
V = 1043.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 293 K
0.21 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.216, T_max = 0.422
10075 measured reflections
2377 independent reflections
1951 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.118
S = 1.04
2377 reflections
200 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −1.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.94 (7)	1.57 (7)	2.501 (4)	171 (7)
O1W—H1A⋯O3ⁱ	0.78 (9)	1.95 (9)	2.726 (5)	174 (9)
O1W—H1B⋯O1ⁱⁱ	0.73 (6)	2.35 (6)	3.007 (5)	150 (5)
Symmetry codes: (i) -x+1, -y, -z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001900/hp2024sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001900/hp2024Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001900/hp2024Isup4.cdx

checkCIF report

Comment top

Li et al. (2009) described the structure of [Zn(C₁₀H₅N₃O₄)H₂O] as a stairway-like two-dimensional 3,3-connected layer held together via hydrogen-bonding interactions involving the carboxylic acid and water H atoms to be a three-dimensional network. The HPyImDC^2- anion behaves as a T-shaped linker (Jing et al., 2010) with one N atoms and bis-N,O-bridging modes chelating the Ni(II) atoms. The present centrosymmetric Ni analogue, (Fig. 1) is isomorphous, the two compounds having nearly identical unit-cell parameters.

As shown in Fig. 2a, the {NiN₃O₃} octahedra connect with the T-shaped HPyImDC^2- anions to be a one-dimensional chain structure extending in the c direction. Then these one-dimensional chains arrange along the b direction to be a two-dimensional layer structure extending in the bc plane (Fig. 2 b), which are further connected through the hydrogen bonds occurred between O(1 W)—H(1 A)···O(3) (-x + 1,-y,-z) and O(1 W)—H(1B)···O(1)(x-1, y, z), respectively, to construct a three-dimensional supramolecular framework (Fig. 2c and Table 1).

Related literature top

For the isotypic Cu compound, see: Li et al. (2009). The HPyImDC^2- anion behaves as a T-shaped linker, see: Jing et al. (2010).

Experimental top

Preparation of the complex.

A solution of NiCl₂6H₂O (0.012 g, 0.5 mmol) and H₃PyImDC (0.012 g, 0.05 mmol) in DMF (1 ml) and H₂O (0.5 ml) was sealed into a 15 ml Teflon-lined stainless autoclave and heated at 433 K for 4 days and then cooled to room temperature gradually to afford well formed green block crystals in about 60% yield (based on Zn). Elemental analysis found (%): C, 39.06; H, 2.30; N, 13.72; Ni, 19.01. H₇C₁₀N₃O₅Ni requires (%): C, 39.01; H, 2.29; N, 13.65; Ni, 19.06. IR (KBr, cm^-1): 3571 (s), 3083 (m), 2560 (w), 1675 (w), 1565 (versus), 1271 (s), 842 (m), 567 (w).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the centrosymmetric molecule of (I), with displacement ellipsoids drawn at the 25% probability level [symmetry code: (i) -x, -y - 1, -z; (ii) x, -y - 1/2, z + 1/2; (iii) x, -y - 1/2, z - 1/2]
	Fig. 2. (a) A view showing the one-dimensional (one-dimensional) chain along the c direction; (b) one-dimensional chains arranged in the b direction to be a two-dimensional layer structure; (c) the two-dimensional layers packed in an AAA way via hydrogen-bonding interactions to be a three-dimensional network.

Poly[aqua[µ₃-4-carboxy-2-(pyridin-4-yl)-1H-imidazole-5-carboxylato- κ⁵N¹,O⁵:N³,O⁴:N²]nickel(II)] top

Crystal data top

[Ni(C₁₀H₅N₃O₄)(H₂O)]	D_x = 1.959 Mg m⁻³
M_r = 307.88	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5117 (15) Å	Cell parameters from 2377 reflections
b = 11.400 (2) Å	θ = 3.3–27.4°
c = 12.896 (4) Å	µ = 1.88 mm⁻¹
β = 109.04 (3)°	T = 293 K
V = 1043.9 (4) Å³	Block, green
Z = 4	0.21 × 0.16 × 0.13 mm
F(000) = 624

Data collection top

Bruker SMART CCD area-detector diffractometer	2377 independent reflections
Radiation source: fine-focus sealed tube	1951 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
Detector resolution: 9.00cm pixels mm^-1	θ_max = 27.4°, θ_min = 3.3°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.216, T_max = 0.422	l = −16→16
10075 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0468P)² + 3.3079P] where P = (F_o² + 2F_c²)/3
2377 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −1.09 e Å⁻³

Crystal data top

[Ni(C₁₀H₅N₃O₄)(H₂O)]	V = 1043.9 (4) Å³
M_r = 307.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5117 (15) Å	µ = 1.88 mm⁻¹
b = 11.400 (2) Å	T = 293 K
c = 12.896 (4) Å	0.21 × 0.16 × 0.13 mm
β = 109.04 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2377 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1951 reflections with I > 2σ(I)
T_min = 0.216, T_max = 0.422	R_int = 0.067
10075 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.55 e Å⁻³
2377 reflections	Δρ_min = −1.09 e Å⁻³
200 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	0.32031 (7)	−0.26730 (4)	0.18242 (4)	0.01465 (17)
O1	0.7267 (4)	−0.0698 (3)	0.1164 (3)	0.0285 (7)
H1	0.740 (10)	−0.063 (6)	0.046 (6)	0.08 (2)*
O2	0.5375 (4)	−0.1450 (3)	0.1996 (2)	0.0234 (7)
O3	0.7296 (4)	−0.0603 (3)	−0.0768 (2)	0.0275 (7)
O4	0.5464 (4)	−0.1211 (2)	−0.2426 (2)	0.0210 (6)
O1W	0.1140 (5)	−0.1417 (3)	0.1203 (3)	0.0243 (7)
H1A	0.163 (12)	−0.087 (8)	0.106 (7)	0.11 (3)*
H1B	0.041 (8)	−0.120 (5)	0.142 (4)	0.030 (16)*
N1	0.3422 (5)	−0.2756 (3)	0.0217 (3)	0.0158 (7)
N2	0.3437 (5)	−0.2632 (3)	−0.1527 (2)	0.0141 (6)
N3	−0.1352 (5)	−0.5920 (3)	−0.1621 (3)	0.0168 (7)
C1	0.5860 (6)	−0.1354 (3)	0.1176 (3)	0.0178 (8)
C2	0.4806 (5)	−0.1986 (3)	0.0175 (3)	0.0142 (8)
C3	0.4813 (5)	−0.1914 (3)	−0.0886 (3)	0.0148 (8)
C4	0.5922 (6)	−0.1201 (3)	−0.1406 (3)	0.0172 (8)
C5	0.2647 (5)	−0.3130 (3)	−0.0826 (3)	0.0144 (8)
C6	0.1198 (5)	−0.4054 (3)	−0.1148 (3)	0.0151 (8)
C7	−0.0568 (6)	−0.3944 (3)	−0.1030 (3)	0.0161 (8)
H7	−0.090 (7)	−0.323 (4)	−0.074 (4)	0.029 (13)*
C8	−0.1783 (6)	−0.4892 (4)	−0.1272 (3)	0.0175 (8)
H8	−0.297 (6)	−0.478 (4)	−0.122 (3)	0.014 (10)*
C9	0.0311 (6)	−0.6007 (4)	−0.1785 (4)	0.0231 (9)
H9	0.047 (6)	−0.676 (4)	−0.206 (4)	0.023 (12)*
C10	0.1607 (6)	−0.5112 (4)	−0.1567 (3)	0.0222 (9)
H10	0.285 (7)	−0.522 (4)	−0.161 (4)	0.030 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0168 (3)	0.0167 (3)	0.0120 (3)	−0.0020 (2)	0.00689 (19)	−0.0009 (2)
O1	0.0247 (17)	0.0394 (19)	0.0202 (16)	−0.0164 (14)	0.0058 (13)	−0.0018 (14)
O2	0.0272 (16)	0.0310 (16)	0.0141 (14)	−0.0091 (13)	0.0097 (12)	−0.0055 (12)
O3	0.0250 (16)	0.0351 (18)	0.0218 (15)	−0.0181 (14)	0.0068 (13)	0.0018 (14)
O4	0.0247 (16)	0.0259 (15)	0.0155 (14)	−0.0076 (12)	0.0107 (12)	0.0026 (12)
O1W	0.0235 (18)	0.0257 (17)	0.0274 (17)	0.0037 (14)	0.0134 (14)	0.0046 (14)
N1	0.0180 (16)	0.0177 (16)	0.0133 (15)	−0.0024 (14)	0.0074 (13)	0.0009 (13)
N2	0.0172 (16)	0.0152 (15)	0.0126 (15)	−0.0023 (13)	0.0085 (13)	0.0000 (13)
N3	0.0197 (17)	0.0187 (16)	0.0124 (15)	−0.0032 (14)	0.0059 (13)	0.0012 (13)
C1	0.018 (2)	0.021 (2)	0.0136 (19)	−0.0036 (16)	0.0045 (16)	0.0010 (16)
C2	0.0104 (18)	0.0183 (19)	0.0136 (18)	−0.0043 (14)	0.0034 (14)	−0.0016 (15)
C3	0.0158 (19)	0.0160 (18)	0.0151 (18)	−0.0024 (15)	0.0087 (15)	0.0015 (15)
C4	0.0165 (19)	0.020 (2)	0.018 (2)	−0.0020 (15)	0.0091 (16)	0.0035 (16)
C5	0.016 (2)	0.0146 (18)	0.0146 (18)	−0.0030 (15)	0.0078 (15)	−0.0009 (15)
C6	0.017 (2)	0.0199 (19)	0.0086 (17)	−0.0038 (16)	0.0054 (14)	0.0005 (15)
C7	0.017 (2)	0.0147 (19)	0.0164 (19)	0.0026 (15)	0.0059 (15)	0.0001 (16)
C8	0.014 (2)	0.023 (2)	0.0166 (19)	0.0025 (16)	0.0065 (15)	0.0073 (16)
C9	0.028 (2)	0.019 (2)	0.027 (2)	−0.0057 (18)	0.0151 (18)	−0.0062 (18)
C10	0.022 (2)	0.026 (2)	0.024 (2)	−0.0044 (17)	0.0150 (18)	−0.0045 (18)

Geometric parameters (Å, º) top

Ni1—O1W	2.070 (3)	N2—C3	1.365 (5)
Ni1—N3ⁱ	2.082 (3)	N2—Ni1ⁱⁱⁱ	2.105 (3)
Ni1—O4ⁱⁱ	2.089 (3)	N3—C8	1.332 (5)
Ni1—O2	2.103 (3)	N3—C9	1.338 (5)
Ni1—N2ⁱⁱ	2.105 (3)	N3—Ni1ⁱ	2.082 (3)
Ni1—N1	2.134 (3)	C1—C2	1.465 (5)
O1—C1	1.299 (5)	C2—C3	1.372 (5)
O1—H1	0.94 (7)	C3—C4	1.474 (5)
O2—C1	1.230 (5)	C5—C6	1.474 (5)
O3—C4	1.285 (5)	C6—C7	1.390 (5)
O4—C4	1.246 (5)	C6—C10	1.396 (6)
O4—Ni1ⁱⁱⁱ	2.089 (3)	C7—C8	1.384 (6)
O1W—H1A	0.78 (9)	C7—H7	0.96 (5)
O1W—H1B	0.73 (6)	C8—H8	0.93 (4)
N1—C5	1.349 (5)	C9—C10	1.374 (6)
N1—C2	1.375 (5)	C9—H9	0.95 (5)
N2—C5	1.356 (5)	C10—H10	0.96 (5)

O1W—Ni1—N3ⁱ	95.68 (14)	O2—C1—O1	122.1 (4)
O1W—Ni1—O4ⁱⁱ	173.34 (13)	O2—C1—C2	119.2 (3)
N3ⁱ—Ni1—O4ⁱⁱ	89.89 (13)	O1—C1—C2	118.7 (3)
O1W—Ni1—O2	92.26 (14)	C3—C2—N1	109.0 (3)
N3ⁱ—Ni1—O2	170.92 (13)	C3—C2—C1	132.3 (3)
O4ⁱⁱ—Ni1—O2	82.49 (12)	N1—C2—C1	118.5 (3)
O1W—Ni1—N2ⁱⁱ	94.71 (13)	N2—C3—C2	108.6 (3)
N3ⁱ—Ni1—N2ⁱⁱ	94.98 (12)	N2—C3—C4	118.9 (3)
O4ⁱⁱ—Ni1—N2ⁱⁱ	81.13 (11)	C2—C3—C4	132.4 (4)
O2—Ni1—N2ⁱⁱ	88.74 (12)	O4—C4—O3	124.6 (4)
O1W—Ni1—N1	86.54 (13)	O4—C4—C3	118.2 (3)
N3ⁱ—Ni1—N1	95.94 (12)	O3—C4—C3	117.1 (3)
O4ⁱⁱ—Ni1—N1	96.54 (12)	N1—C5—N2	113.1 (3)
O2—Ni1—N1	80.11 (11)	N1—C5—C6	123.1 (3)
N2ⁱⁱ—Ni1—N1	168.83 (12)	N2—C5—C6	123.7 (3)
C1—O1—H1	114 (4)	C7—C6—C10	117.3 (4)
C1—O2—Ni1	113.9 (3)	C7—C6—C5	123.2 (4)
C4—O4—Ni1ⁱⁱⁱ	113.4 (2)	C10—C6—C5	119.4 (3)
Ni1—O1W—H1A	107 (6)	C8—C7—C6	119.2 (4)
Ni1—O1W—H1B	130 (4)	C8—C7—H7	121 (3)
H1A—O1W—H1B	107 (7)	C6—C7—H7	120 (3)
C5—N1—C2	104.4 (3)	N3—C8—C7	123.3 (4)
C5—N1—Ni1	146.9 (3)	N3—C8—H8	119 (3)
C2—N1—Ni1	108.0 (2)	C7—C8—H8	117 (3)
C5—N2—C3	104.9 (3)	N3—C9—C10	123.2 (4)
C5—N2—Ni1ⁱⁱⁱ	146.2 (3)	N3—C9—H9	111 (3)
C3—N2—Ni1ⁱⁱⁱ	108.1 (2)	C10—C9—H9	126 (3)
C8—N3—C9	117.5 (3)	C9—C10—C6	119.4 (4)
C8—N3—Ni1ⁱ	119.6 (3)	C9—C10—H10	122 (3)
C9—N3—Ni1ⁱ	122.9 (3)	C6—C10—H10	118 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.94 (7)	1.57 (7)	2.501 (4)	171 (7)
O1W—H1A···O3^iv	0.78 (9)	1.95 (9)	2.726 (5)	174 (9)
O1W—H1B···O1^v	0.73 (6)	2.35 (6)	3.007 (5)	150 (5)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₅N₃O₄)(H₂O)]
M_r	307.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5117 (15), 11.400 (2), 12.896 (4)
β (°)	109.04 (3)
V (Å³)	1043.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.21 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.216, 0.422
No. of measured, independent and observed [I > 2σ(I)] reflections	10075, 2377, 1951
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.118, 1.04
No. of reflections	2377
No. of parameters	200
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −1.09

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.94 (7)	1.57 (7)	2.501 (4)	171 (7)
O1W—H1A···O3ⁱ	0.78 (9)	1.95 (9)	2.726 (5)	174 (9)
O1W—H1B···O1ⁱⁱ	0.73 (6)	2.35 (6)	3.007 (5)	150 (5)

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

Acknowledgements

This work was supported by the Second Self-financing Project of Langfang Scientific and Technological Research and the Development Program of Hebei Province of the People's Republic of China (grant No. 2011011037).

References

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