catena-Poly[[[[3-(2-pyrid­yl)-1H-pyra­zole]nickel(II)]-μ-oxalato] sesquihydrate]

Jiang, B.; Liu, Z.

doi:10.1107/S1600536809026117

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages m898-m899

doi:10.1107/S1600536809026117

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catena-Poly[[[[3-(2-pyridyl)-1H-pyrazole]nickel(II)]-μ-oxalato] sesquihydrate]

Bin Jiang ^a and Zhilu Liu ^b ^*

^aDepartment of Pharmacy, Shandong Medical College, Jinan 250002, People's Republic of China, and ^bState Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 73000, People's Republic of China
^*Correspondence e-mail: liuzhilu2009@yahoo.com.cn

(Received 25 June 2009; accepted 5 July 2009; online 11 July 2009)

In the title compound, {[Ni(C₂O₄)(C₈H₇N₃)]·1.5H₂O}_n, both unique Ni^II ions are chelated by an O,O′-bidentate oxalate ion and an N,N′-bidentate 3-(2-pyridyl)pyrazole molecule. A second, symmetry-generated, oxalate ion completes a distorted cis-NiN₂O₄ octahedral geometry for both metal centres. The bridging oxalate ions result in two distinct wave-like polymeric chains propagating in [100]. The packing is consolidated by N—H⋯O and O—H⋯O hydrogen bonds. The crystal studied was found to be an inversion twin.

Related literature

For related literature on coordination polymers, see: Ward (2007 ).

Experimental

Crystal data

[Ni(C₂O₄)(C₈H₇N₃)]·1.5H₂O
M_r = 318.92
Orthorhombic, P n a 2₁
a = 9.763 (2) Å
b = 9.1970 (18) Å
c = 29.352 (6) Å
V = 2635.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 1.50 mm⁻¹
T = 293 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.841, T_max = 0.890
17815 measured reflections
4882 independent reflections
3723 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.139
S = 1.00
4882 reflections
385 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 2287 Friedel pairs
Flack parameter: 0.50 (3)

Table 1
Selected bond lengths (Å)

Ni1—O1	2.152 (5)
Ni1—O3	2.200 (6)
Ni1—O2ⁱ	2.163 (6)
Ni1—O4ⁱ	2.177 (4)
Ni1—N1	2.259 (6)
Ni1—N2	2.230 (6)
Ni2—O6	2.159 (6)
Ni2—O8	2.188 (4)
Ni2—O5ⁱⁱ	2.142 (4)
Ni2—O7ⁱⁱ	2.217 (6)
Ni2—N4	2.285 (6)
Ni2—N5	2.205 (6)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O11ⁱⁱⁱ	0.97 (4)	1.81 (2)	2.745 (10)	160 (5)
N6—H6A⋯O10^iv	0.98 (16)	2.0 (2)	2.732 (9)	133 (5)
O9—H2W⋯O7^v	0.82 (4)	2.02 (4)	2.822 (9)	166 (6)
O9—H1W⋯O11^vi	0.82 (12)	2.22 (15)	2.813 (11)	130 (16)
O10—H3W⋯O4^vii	0.82 (5)	2.30 (7)	2.834 (9)	123 (7)
O10—H4W⋯O9^vi	0.82 (4)	2.08 (3)	2.811 (11)	148 (5)
O11—H5W⋯O9^viii	0.82 (5)	2.15 (4)	2.813 (11)	138 (5)
O11—H6W⋯O8^ix	0.82 (4)	2.17 (4)	2.876 (9)	144 (6)
Symmetry codes: (iii) $[-x+1, -y+2, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (vi) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (vii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (viii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ix) x, y+1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026117/hb5014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026117/hb5014Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of coordination polymers (Ward, 2007), we now report the synthesis and crystal structural characterization of the title compound, (I).

The N^II ions are hexcoordianted, chelated by two oxalate and one 3-(2-pyridyl)pyrazole ligand (Table 1). While each oxalate ligand acts as one bridige to chalate two Ni ions, forming one wave-like line with Ni···Ni distance being 5.562 Å, shown in Figure 2. The structure is consolidated by N—H···O and O—H···O hydrogen bonds (Table 2, Figure 3).

Related literature top

For related literature on coordination polymers, see: Ward (2007).

Experimental top

The synthesis was performed in a 25 ml Teflon-lined stainless steel vessel: NiCl₂ (1 mmol), 3-(2-pyridyl)pyrazole (1 mmol), oxalic acid (1 mmol), and H₂O (10 ml) were mixed and heated to 433 K for three days. On cooling, green blocks of (I) were recovered. Anal. Calc. for C₂₀H₂₀Ni₂N₆O₁₁: C 37.60, H 3.13, N 13.16%; Found: 37.56, H 3.06, N 13.10%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I) with the unique atoms labelled. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the chain strcuture of (I).
	Fig. 3. A view of the packing strcuture of (I).

catena-Poly[[[[3-(2-pyridyl)-1<>H-pyrazole]nickel(II)]-µ-oxalato] sesquihydrate] top

Crystal data top

[Ni(C₂O₄)(C₈H₇N₃)]·1.5H₂O	F(000) = 1304
M_r = 318.92	D_x = 1.607 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4779 reflections
a = 9.763 (2) Å	θ = 2.3–25.5°
b = 9.1970 (18) Å	µ = 1.50 mm⁻¹
c = 29.352 (6) Å	T = 293 K
V = 2635.5 (9) Å³	Block, green
Z = 8	0.12 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4882 independent reflections
Radiation source: fine-focus sealed tube	3723 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.841, T_max = 0.890	k = −11→10
17815 measured reflections	l = −35→35

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.078P)² + 0.5477P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4882 reflections	Δρ_max = 0.47 e Å⁻³
385 parameters	Δρ_min = −0.37 e Å⁻³
12 restraints	Absolute structure: Flack (1983), 2287 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.50 (3)

Crystal data top

[Ni(C₂O₄)(C₈H₇N₃)]·1.5H₂O	V = 2635.5 (9) Å³
M_r = 318.92	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.763 (2) Å	µ = 1.50 mm⁻¹
b = 9.1970 (18) Å	T = 293 K
c = 29.352 (6) Å	0.12 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4882 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3723 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.890	R_int = 0.059
17815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.139	Δρ_max = 0.47 e Å⁻³
S = 1.00	Δρ_min = −0.37 e Å⁻³
4882 reflections	Absolute structure: Flack (1983), 2287 Friedel pairs
385 parameters	Absolute structure parameter: 0.50 (3)
12 restraints

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	0.31148 (9)	1.09616 (9)	0.84957 (7)	0.0406 (2)
Ni2	0.55514 (8)	−0.09515 (9)	0.08796 (7)	0.0408 (2)
C1	0.3921 (9)	0.0950 (8)	0.0119 (3)	0.049 (2)
H1	0.3731	0.0049	−0.0010	0.059*
C2	0.3379 (10)	0.2187 (11)	−0.0082 (4)	0.062 (2)
H2	0.2809	0.2111	−0.0335	0.074*
C3	0.3688 (12)	0.3506 (12)	0.0094 (3)	0.077 (4)
H3	0.3325	0.4349	−0.0033	0.092*
C4	0.4564 (11)	0.3578 (10)	0.0472 (4)	0.060 (3)
H4	0.4850	0.4472	0.0585	0.073*
C5	0.4996 (10)	0.2304 (8)	0.0671 (3)	0.041 (2)
C6	0.5898 (9)	0.2314 (8)	0.1082 (3)	0.036 (2)
C7	0.6452 (10)	0.3438 (9)	0.1323 (4)	0.062 (3)
H7	0.6355	0.4430	0.1270	0.075*
C8	0.7179 (10)	0.2767 (11)	0.1658 (4)	0.061 (3)
H8	0.7664	0.3233	0.1888	0.073*
C9	0.3240 (8)	−0.2826 (8)	0.0649 (3)	0.0342 (19)
C10	0.2918 (7)	−0.2229 (7)	0.1133 (3)	0.0254 (15)
C11	0.5767 (6)	1.2152 (8)	0.8712 (2)	0.0236 (13)
C12	0.5476 (8)	1.2747 (8)	0.8228 (3)	0.0325 (18)
C13	0.1336 (9)	0.9194 (11)	0.9256 (3)	0.057 (2)
H13	0.1073	1.0111	0.9357	0.069*
C14	0.0855 (11)	0.7996 (12)	0.9485 (3)	0.071 (3)
H14	0.0292	0.8096	0.9738	0.085*
C15	0.1225 (10)	0.6663 (12)	0.9331 (4)	0.070 (3)
H15	0.0937	0.5844	0.9490	0.084*
C16	0.1990 (10)	0.6493 (10)	0.8960 (4)	0.060 (3)
H16	0.2158	0.5570	0.8843	0.072*
C17	0.2534 (9)	0.7723 (8)	0.8749 (3)	0.0372 (19)
C18	0.3377 (9)	0.7695 (8)	0.8356 (3)	0.040 (2)
C19	0.3938 (12)	0.6511 (11)	0.8106 (4)	0.071 (3)
H19	0.3789	0.5526	0.8157	0.085*
C20	0.4713 (14)	0.7090 (12)	0.7784 (5)	0.088 (4)
H20	0.5256	0.6582	0.7579	0.106*
N1	0.2170 (6)	0.9107 (6)	0.8890 (2)	0.0378 (15)
N2	0.3773 (6)	0.8926 (7)	0.8146 (2)	0.0384 (15)
N3	0.4576 (7)	0.8577 (8)	0.7808 (2)	0.0516 (18)
N4	0.4710 (6)	0.1009 (6)	0.0492 (2)	0.0353 (14)
N5	0.6263 (6)	0.1013 (7)	0.1239 (2)	0.0375 (14)
N6	0.7085 (8)	0.1366 (9)	0.1604 (2)	0.0536 (19)
O1	0.4923 (5)	1.1355 (5)	0.88962 (16)	0.0351 (10)
O2	0.6957 (5)	1.2463 (5)	0.8884 (3)	0.0398 (17)
O3	0.4389 (5)	1.2387 (5)	0.8069 (2)	0.0347 (16)
O4	0.6367 (5)	1.3553 (5)	0.80613 (16)	0.0354 (10)
O5	0.2318 (4)	−0.3592 (5)	0.04713 (16)	0.0335 (10)
O6	0.4326 (5)	−0.2429 (5)	0.0479 (3)	0.0378 (17)
O7	0.1787 (6)	−0.2608 (6)	0.1324 (2)	0.0385 (17)
O8	0.3784 (4)	−0.1410 (5)	0.13145 (17)	0.0383 (11)
O9	0.6278 (8)	0.6448 (6)	0.2198 (2)	0.0605 (12)
O10	0.8552 (8)	0.9517 (8)	0.2145 (2)	0.0727 (17)
O11	0.3970 (8)	0.9636 (7)	0.2236 (2)	0.0667 (16)
H6W	0.412 (4)	0.905 (5)	0.2033 (15)	0.077 (17)*
H2W	0.632 (6)	0.689 (6)	0.1956 (11)	0.074 (19)*
H1W	0.672 (16)	0.569 (10)	0.221 (3)	0.083 (10)*
H3W	0.860 (5)	0.989 (8)	0.2399 (12)	0.085 (2)*
H4W	0.927 (3)	0.918 (7)	0.2051 (17)	0.093 (2)*
H5W	0.321 (4)	0.957 (7)	0.235 (3)	0.107 (4)*
H3A	0.490 (5)	0.935 (4)	0.7611 (14)	0.064 (13)*
H6A	0.71 (3)	0.069 (18)	0.186 (5)	0.059 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0366 (4)	0.0418 (5)	0.0432 (5)	−0.0004 (4)	0.0012 (4)	0.0039 (5)
Ni2	0.0352 (4)	0.0420 (5)	0.0453 (5)	0.0012 (4)	−0.0004 (4)	−0.0020 (5)
C1	0.064 (5)	0.039 (4)	0.045 (4)	0.017 (4)	−0.007 (4)	−0.010 (3)
C2	0.070 (6)	0.072 (6)	0.044 (5)	0.024 (5)	−0.019 (4)	−0.002 (5)
C3	0.116 (9)	0.074 (7)	0.041 (5)	0.056 (6)	−0.014 (5)	0.004 (5)
C4	0.092 (7)	0.037 (5)	0.053 (5)	0.014 (4)	−0.001 (5)	−0.008 (4)
C5	0.047 (5)	0.039 (4)	0.039 (5)	0.016 (4)	0.012 (4)	0.007 (3)
C6	0.043 (4)	0.030 (4)	0.035 (5)	0.005 (3)	−0.016 (3)	0.005 (3)
C7	0.081 (6)	0.024 (4)	0.082 (7)	−0.015 (4)	−0.021 (6)	−0.010 (4)
C8	0.062 (5)	0.057 (5)	0.062 (6)	−0.012 (5)	−0.037 (5)	−0.015 (5)
C9	0.051 (5)	0.024 (3)	0.028 (4)	0.025 (4)	0.000 (3)	−0.011 (3)
C10	0.016 (3)	0.031 (3)	0.029 (4)	−0.002 (3)	0.002 (3)	0.000 (3)
C11	0.016 (3)	0.027 (3)	0.028 (3)	−0.016 (3)	−0.002 (2)	−0.002 (3)
C12	0.037 (5)	0.031 (3)	0.029 (4)	0.010 (3)	0.005 (3)	0.007 (3)
C13	0.060 (5)	0.077 (6)	0.035 (4)	−0.011 (4)	0.008 (4)	−0.001 (4)
C14	0.095 (7)	0.082 (7)	0.035 (5)	−0.046 (7)	0.021 (5)	0.007 (5)
C15	0.082 (7)	0.055 (6)	0.071 (7)	−0.026 (5)	0.006 (5)	0.033 (5)
C16	0.065 (5)	0.033 (5)	0.083 (7)	−0.018 (4)	0.010 (5)	0.017 (5)
C17	0.044 (5)	0.031 (4)	0.038 (5)	−0.005 (3)	0.005 (4)	0.001 (3)
C18	0.036 (4)	0.031 (4)	0.051 (6)	0.000 (3)	−0.011 (4)	−0.004 (3)
C19	0.096 (8)	0.038 (5)	0.079 (7)	−0.002 (5)	0.024 (6)	0.006 (5)
C20	0.124 (10)	0.046 (5)	0.095 (10)	0.030 (7)	0.036 (8)	−0.023 (7)
N1	0.043 (3)	0.035 (4)	0.036 (3)	−0.002 (2)	0.006 (3)	0.004 (3)
N2	0.037 (3)	0.034 (3)	0.044 (3)	0.006 (2)	0.005 (3)	0.003 (3)
N3	0.050 (4)	0.047 (4)	0.058 (5)	0.009 (3)	0.019 (3)	−0.001 (3)
N4	0.035 (3)	0.037 (3)	0.034 (3)	0.016 (2)	−0.006 (2)	−0.007 (3)
N5	0.041 (3)	0.036 (3)	0.036 (3)	0.000 (3)	−0.014 (3)	−0.004 (3)
N6	0.061 (4)	0.058 (5)	0.042 (4)	−0.005 (3)	−0.027 (3)	0.000 (3)
O1	0.034 (2)	0.043 (3)	0.029 (2)	−0.001 (2)	−0.004 (2)	0.009 (2)
O2	0.042 (4)	0.042 (4)	0.035 (4)	−0.009 (2)	−0.019 (3)	0.0142 (19)
O3	0.023 (3)	0.045 (4)	0.036 (4)	−0.0085 (19)	−0.005 (2)	0.012 (2)
O4	0.034 (2)	0.041 (3)	0.031 (2)	−0.009 (2)	−0.0058 (19)	0.008 (2)
O5	0.030 (2)	0.039 (2)	0.032 (2)	−0.006 (2)	0.006 (2)	−0.011 (2)
O6	0.022 (3)	0.056 (4)	0.036 (4)	−0.0070 (19)	0.006 (2)	−0.018 (2)
O7	0.035 (3)	0.054 (4)	0.026 (4)	−0.015 (2)	0.016 (2)	−0.008 (2)
O8	0.028 (2)	0.052 (3)	0.035 (3)	−0.005 (2)	0.003 (2)	−0.016 (2)
O9	0.090 (4)	0.057 (3)	0.034 (2)	−0.003 (4)	0.015 (2)	0.007 (3)
O10	0.078 (5)	0.096 (5)	0.043 (4)	0.011 (4)	−0.014 (4)	0.017 (4)
O11	0.084 (5)	0.071 (4)	0.045 (4)	−0.006 (4)	−0.011 (4)	−0.005 (3)

Geometric parameters (Å, º) top

Ni1—O1	2.152 (5)	C11—O2	1.299 (8)
Ni1—O3	2.200 (6)	C11—C12	1.550 (11)
Ni1—O2ⁱ	2.163 (6)	C12—O3	1.206 (10)
Ni1—O4ⁱ	2.177 (4)	C12—O4	1.243 (9)
Ni1—N1	2.259 (6)	C13—N1	1.349 (11)
Ni1—N2	2.230 (6)	C13—C14	1.374 (12)
Ni2—O6	2.159 (6)	C13—H13	0.9300
Ni2—O8	2.188 (4)	C14—C15	1.355 (16)
Ni2—O5ⁱⁱ	2.142 (4)	C14—H14	0.9300
Ni2—O7ⁱⁱ	2.217 (6)	C15—C16	1.330 (15)
Ni2—N4	2.285 (6)	C15—H15	0.9300
Ni2—N5	2.205 (6)	C16—C17	1.395 (11)
C1—N4	1.340 (11)	C16—H16	0.9300
C1—C2	1.386 (11)	C17—N1	1.385 (10)
C1—H1	0.9300	C17—C18	1.416 (13)
C2—C3	1.353 (14)	C18—N2	1.346 (10)
C2—H2	0.9300	C18—C19	1.424 (13)
C3—C4	1.401 (15)	C19—C20	1.321 (17)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.376 (12)	C20—N3	1.376 (12)
C4—H4	0.9300	C20—H20	0.9300
C5—N4	1.331 (10)	N2—N3	1.304 (9)
C5—C6	1.494 (13)	N3—H3A	0.97 (4)
C6—N5	1.331 (9)	N5—N6	1.376 (9)
C6—C7	1.363 (12)	N6—H6A	0.98 (16)
C7—C8	1.362 (15)	O2—Ni1ⁱⁱⁱ	2.163 (6)
C7—H7	0.9300	O4—Ni1ⁱⁱⁱ	2.177 (4)
C8—N6	1.301 (11)	O5—Ni2^iv	2.142 (4)
C8—H8	0.9300	O7—Ni2^iv	2.217 (6)
C9—O6	1.227 (9)	O9—H2W	0.82 (4)
C9—O5	1.257 (9)	O9—H1W	0.82 (12)
C9—C10	1.555 (10)	O10—H3W	0.82 (5)
C10—O8	1.251 (8)	O10—H4W	0.82 (4)
C10—O7	1.287 (9)	O11—H6W	0.82 (4)
C11—O1	1.228 (7)	O11—H5W	0.82 (5)

O1—Ni1—O2ⁱ	91.6 (2)	O1—C11—O2	124.2 (7)
O1—Ni1—O4ⁱ	158.28 (17)	O1—C11—C12	119.4 (6)
O2ⁱ—Ni1—O4ⁱ	76.2 (2)	O2—C11—C12	116.3 (6)
O1—Ni1—O3	75.4 (2)	O3—C12—O4	128.8 (8)
O2ⁱ—Ni1—O3	101.4 (2)	O3—C12—C11	114.9 (7)
O4ⁱ—Ni1—O3	89.3 (2)	O4—C12—C11	116.3 (7)
O1—Ni1—N2	99.0 (2)	N1—C13—C14	123.2 (9)
O2ⁱ—Ni1—N2	162.9 (2)	N1—C13—H13	118.4
O4ⁱ—Ni1—N2	97.4 (2)	C14—C13—H13	118.4
O3—Ni1—N2	94.3 (2)	C15—C14—C13	118.2 (9)
O1—Ni1—N1	100.5 (2)	C15—C14—H14	120.9
O2ⁱ—Ni1—N1	91.3 (2)	C13—C14—H14	120.9
O4ⁱ—Ni1—N1	97.8 (2)	C16—C15—C14	121.9 (8)
O3—Ni1—N1	166.7 (2)	C16—C15—H15	119.0
N2—Ni1—N1	73.7 (2)	C14—C15—H15	119.1
O5ⁱⁱ—Ni2—O6	91.0 (2)	C15—C16—C17	118.8 (9)
O5ⁱⁱ—Ni2—O8	157.52 (16)	C15—C16—H16	120.6
O6—Ni2—O8	76.1 (2)	C17—C16—H16	120.6
O5ⁱⁱ—Ni2—N5	100.1 (2)	N1—C17—C16	121.0 (8)
O6—Ni2—N5	162.0 (2)	N1—C17—C18	114.2 (7)
O8—Ni2—N5	97.3 (2)	C16—C17—C18	124.6 (8)
O5ⁱⁱ—Ni2—O7ⁱⁱ	76.95 (19)	N2—C18—C17	121.7 (7)
O6—Ni2—O7ⁱⁱ	104.2 (2)	N2—C18—C19	107.2 (8)
O8—Ni2—O7ⁱⁱ	88.3 (2)	C17—C18—C19	131.2 (8)
N5—Ni2—O7ⁱⁱ	92.1 (2)	C20—C19—C18	106.3 (8)
O5ⁱⁱ—Ni2—N4	99.5 (2)	C20—C19—H19	126.8
O6—Ni2—N4	91.5 (2)	C18—C19—H19	126.9
O8—Ni2—N4	99.2 (2)	C19—C20—N3	108.0 (9)
N5—Ni2—N4	72.9 (2)	C19—C20—H20	126.0
O7ⁱⁱ—Ni2—N4	163.9 (2)	N3—C20—H20	126.0
N4—C1—C2	122.3 (8)	C13—N1—C17	116.6 (7)
N4—C1—H1	118.9	C13—N1—Ni1	127.5 (6)
C2—C1—H1	118.9	C17—N1—Ni1	115.8 (5)
C3—C2—C1	119.2 (9)	N3—N2—C18	108.4 (7)
C3—C2—H2	120.4	N3—N2—Ni1	136.9 (5)
C1—C2—H2	120.4	C18—N2—Ni1	114.3 (5)
C2—C3—C4	118.7 (8)	N2—N3—C20	109.9 (8)
C2—C3—H3	120.6	N2—N3—H3A	118 (3)
C4—C3—H3	120.6	C20—N3—H3A	132 (3)
C5—C4—C3	118.9 (9)	C5—N4—C1	118.6 (7)
C5—C4—H4	120.6	C5—N4—Ni2	115.7 (5)
C3—C4—H4	120.6	C1—N4—Ni2	125.6 (5)
N4—C5—C4	122.0 (9)	C6—N5—N6	102.3 (6)
N4—C5—C6	116.6 (7)	C6—N5—Ni2	119.1 (5)
C4—C5—C6	121.2 (8)	N6—N5—Ni2	138.5 (5)
N5—C6—C7	113.3 (8)	C8—N6—N5	111.7 (7)
N5—C6—C5	115.6 (7)	C8—N6—H6A	123 (10)
C7—C6—C5	131.1 (8)	N5—N6—H6A	116 (10)
C6—C7—C8	103.7 (8)	C11—O1—Ni1	114.3 (4)
C6—C7—H7	128.1	C11—O2—Ni1ⁱⁱⁱ	114.2 (5)
C8—C7—H7	128.1	C12—O3—Ni1	116.1 (6)
N6—C8—C7	108.9 (7)	C12—O4—Ni1ⁱⁱⁱ	116.1 (5)
N6—C8—H8	125.6	C9—O5—Ni2^iv	117.1 (4)
C7—C8—H8	125.6	C9—O6—Ni2	116.4 (6)
O6—C9—O5	128.1 (7)	C10—O7—Ni2^iv	111.8 (5)
O6—C9—C10	116.2 (7)	C10—O8—Ni2	113.6 (4)
O5—C9—C10	115.6 (6)	H2W—O9—H1W	116 (8)
O8—C10—O7	123.8 (8)	H3W—O10—H4W	115 (5)
O8—C10—C9	117.7 (6)	H6W—O11—H5W	114 (6)
O7—C10—C9	118.5 (6)

Symmetry codes: (i) x−1/2, −y+5/2, z; (ii) x+1/2, −y−1/2, z; (iii) x+1/2, −y+5/2, z; (iv) x−1/2, −y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O11^v	0.97 (4)	1.81 (2)	2.745 (10)	160 (5)
N6—H6A···O10^vi	0.98 (16)	2.0 (2)	2.732 (9)	133 (5)
O9—H2W···O7^vii	0.82 (4)	2.02 (4)	2.822 (9)	166 (6)
O9—H1W···O11^viii	0.82 (12)	2.22 (15)	2.813 (11)	130 (16)
O10—H3W···O4^ix	0.82 (5)	2.30 (7)	2.834 (9)	123 (7)
O10—H4W···O9^viii	0.82 (4)	2.08 (3)	2.811 (11)	148 (5)
O11—H5W···O9^x	0.82 (5)	2.15 (4)	2.813 (11)	138 (5)
O11—H6W···O8^xi	0.82 (4)	2.17 (4)	2.876 (9)	144 (6)

Symmetry codes: (v) −x+1, −y+2, z+1/2; (vi) x, y−1, z; (vii) x+1/2, −y+1/2, z; (viii) x+1/2, −y+3/2, z; (ix) −x+3/2, y−1/2, z−1/2; (x) x−1/2, −y+3/2, z; (xi) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₂O₄)(C₈H₇N₃)]·1.5H₂O
M_r	318.92
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	9.763 (2), 9.1970 (18), 29.352 (6)
V (Å³)	2635.5 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.841, 0.890
No. of measured, independent and observed [I > 2σ(I)] reflections	17815, 4882, 3723
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.139, 1.00
No. of reflections	4882
No. of parameters	385
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.37
Absolute structure	Flack (1983), 2287 Friedel pairs
Absolute structure parameter	0.50 (3)

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O1	2.152 (5)	Ni2—O6	2.159 (6)
Ni1—O3	2.200 (6)	Ni2—O8	2.188 (4)
Ni1—O2ⁱ	2.163 (6)	Ni2—O5ⁱⁱ	2.142 (4)
Ni1—O4ⁱ	2.177 (4)	Ni2—O7ⁱⁱ	2.217 (6)
Ni1—N1	2.259 (6)	Ni2—N4	2.285 (6)
Ni1—N2	2.230 (6)	Ni2—N5	2.205 (6)

Symmetry codes: (i) x−1/2, −y+5/2, z; (ii) x+1/2, −y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O11ⁱⁱⁱ	0.97 (4)	1.81 (2)	2.745 (10)	160 (5)
N6—H6A···O10^iv	0.98 (16)	2.0 (2)	2.732 (9)	133 (5)
O9—H2W···O7^v	0.82 (4)	2.02 (4)	2.822 (9)	166 (6)
O9—H1W···O11^vi	0.82 (12)	2.22 (15)	2.813 (11)	130 (16)
O10—H3W···O4^vii	0.82 (5)	2.30 (7)	2.834 (9)	123 (7)
O10—H4W···O9^vi	0.82 (4)	2.08 (3)	2.811 (11)	148 (5)
O11—H5W···O9^viii	0.82 (5)	2.15 (4)	2.813 (11)	138 (5)
O11—H6W···O8^ix	0.82 (4)	2.17 (4)	2.876 (9)	144 (6)

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

Acknowledgements

This work was supported by the Chinese Academy of Sciences (Hundred Talents Program) and the Ministry of Science and Technology of China (project of `973' plan, No. 2007CB607606)

References

Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ward, M. D. (2007). Coord. Chem. Rev. 251, 1663–1677. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Pages m898-m899

doi:10.1107/S1600536809026117

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

catena-Poly[[[[3-(2-pyrid­yl)-1H-pyra­zole]nickel(II)]-μ-oxalato] sesquihydrate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[[3-(2-pyridyl)-1H-pyrazole]nickel(II)]-μ-oxalato] sesquihydrate]