catena-Poly[[(2,2′-bipyridine)­nickel(II)]-μ-2,4′-oxydibenzoato]

Xu, J.-K.; Sun, X.-C.; Guo, F.

doi:10.1107/S1600536810046210

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1574

https://doi.org/10.1107/S1600536810046210

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catena-Poly[[(2,2′-bipyridine)nickel(II)]-μ-2,4′-oxydibenzoato]

Jia-Kun Xu,^a Xiao-Chun Sun ^b and Feng Guo ^c ^*

^aCollege of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, People's Republic of China, ^bNational Oceanographic Center, Qingdao 266071, People's Republic of China, and ^cDepartment of Chemistry, Dezhou University, Shandong 253023, People's Republic of China
^*Correspondence e-mail: guofeng1510@yeah.net

(Received 13 October 2010; accepted 9 November 2010; online 13 November 2010)

In the title compound, [Ni(C₁₄H₈O₅)(C₁₀H₈N₂)]_n, the Ni^II atom is six-coordinated in a slightly distorted octahedral geometry by four O atoms from two chelating carboxylate groups of symmetry-related 2,4′-oxydibenzoate anions and by two N atoms from a 2,2′-bipyridine ligand. The Ni^II atoms are bridged by the 2,4′-oxydibenzoate anions, resulting in the formation of helical chains parallel to [010] with a repeating unit of 15.039 (2) Å.

Related literature

For background to multicarboxylate ligands, see: Liu et al. (2008 ); Yang et al. (2009 ).

Experimental

Crystal data

[Ni(C₁₄H₈O₅)(C₁₀H₈N₂)]
M_r = 471.10
Monoclinic, P 2₁ /c
a = 8.061 (1) Å
b = 15.039 (2) Å
c = 17.847 (5) Å
β = 99.464 (3)°
V = 2134.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.764, T_max = 0.833
13096 measured reflections
4938 independent reflections
3475 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.04
4938 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.0260 (17)
Ni1—N2	2.0412 (18)
Ni1—O5ⁱ	2.0459 (19)
Ni1—O1	2.0694 (16)
Ni1—O2	2.1331 (18)
Ni1—O4ⁱ	2.1673 (15)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810046210/wm2416sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046210/wm2416Isup2.hkl

checkCIF report

Comment top

Semi-rigid V-shaped multicarboxylate moieties with two benzene rings containing a central nonmetallic fragment (C, O, or S atom) are excellent ligands since they can freely twist around the nonmetallic atom to meet the requirements of the coordination geometries of metal atoms in the assembly process (Liu et al., 2008; Yang et al., 2009). In view of the above point, we chose 2,4'-oxydibenzoate along with nitrogen-containing auxiliary ligands to construct new metal coordination polymers. The title compound, (I), was synthesized by the hydrothermal reaction of 2,4'-oxybis(benzoic acid) with 2,2-bipyridine and nickel chloride hexahydrate.

The asymmetric unit of (I) consists of one Ni^II ion, one 2,2'-bipyridine ligand and one 2,4'-oxydibenzoate anion. The central Ni^II ion exhibits an octahedral NiN₂O₄ environment defined by two chelating carboxylate groups of symmetry-related 2,4'-oxydibenzoate ligands and by one 2,2-bipyridine molecule (Fig. 1). The Ni—O distances range from 2.0459 (19) to 2.1673 (15) Å and the Ni—N distances from 2.0260 (17) and 2.0412 (18) Å. The 2,4'-oxydibenzoate anions acts as a µ₂-ligand with its two carboxylate groups bridging two Ni^II ions to form an infinite one-dimensional helical chain running parallel to [010] (Fig. 2). The repeating unit of 15.039 (2) Å of the chains corresponds to the lattice parameter b.

Related literature top

For background to multicarboxylate ligands, see: Liu et al. (2008); Yang et al. (2009).

Experimental top

A mixture of NiCl₂^.6H₂O (0.238 g, 1 mmol), 2,4'-oxybis(benzoic acid) (0.258 g, 1 mmol), NaOH (0.08 g, 2 mmol), 2,2'-bipyridine (0.156 g,1 mmol) and distilled water (15 ml) was heated to 433 K for 96 h in a 25 ml stainless steel reactor with a Teflon liner. Green block-like crystals were obtained with 42% yield based on Ni.

Structure description top

For background to multicarboxylate ligands, see: Liu et al. (2008); Yang et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment of the Ni^II atom with displacement parameters drawn at the 40% probability level. All hydrogen atoms have been omitted for clarity. [Symmetry code A: (i) -x+1, y+1/2, -z+3/2].
	Fig. 2. The helical chain (space-filling representation) in (I) extending parallel to [010].

catena-Poly[[(2,2'-bipyridine)nickel(II)]-µ-2,4'-oxydibenzoato] top

Crystal data top

[Ni(C₁₄H₈O₅)(C₁₀H₈N₂)]	F(000) = 968
M_r = 471.10	D_x = 1.466 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3464 reflections
a = 8.061 (1) Å	θ = 2.3–24.4°
b = 15.039 (2) Å	µ = 0.95 mm⁻¹
c = 17.847 (5) Å	T = 293 K
β = 99.464 (3)°	Block, green
V = 2134.1 (6) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4938 independent reflections
Radiation source: fine-focus sealed tube	3475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 27.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→5
T_min = 0.764, T_max = 0.833	k = −18→19
13096 measured reflections	l = −22→23

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) = 0.094	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0451P)² + 0.1348P] where P = (F_o² + 2F_c²)/3
4938 reflections	(Δ/σ)_max = 0.002
289 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Ni(C₁₄H₈O₅)(C₁₀H₈N₂)]	V = 2134.1 (6) Å³
M_r = 471.10	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.061 (1) Å	µ = 0.95 mm⁻¹
b = 15.039 (2) Å	T = 293 K
c = 17.847 (5) Å	0.30 × 0.25 × 0.20 mm
β = 99.464 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4938 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3475 reflections with I > 2σ(I)
T_min = 0.764, T_max = 0.833	R_int = 0.027
13096 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
4938 reflections	Δρ_min = −0.22 e Å⁻³
289 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	0.68282 (3)	0.376038 (17)	0.855723 (14)	0.04554 (11)
O3	0.26452 (19)	−0.09960 (9)	0.91468 (8)	0.0506 (4)
O4	0.31673 (18)	−0.13651 (9)	0.76522 (8)	0.0506 (4)
O2	0.45649 (19)	0.30889 (9)	0.86917 (8)	0.0537 (4)
C1	0.5405 (3)	0.23738 (14)	0.87422 (11)	0.0477 (5)
O5	0.09217 (19)	−0.11077 (10)	0.68204 (8)	0.0556 (4)
C13	0.1600 (3)	−0.12592 (12)	0.74953 (12)	0.0428 (5)
O1	0.69556 (18)	0.23953 (9)	0.87013 (9)	0.0552 (4)
C5	0.3211 (3)	−0.01512 (13)	0.90085 (10)	0.0441 (5)
C12	0.0473 (3)	−0.13366 (12)	0.80753 (11)	0.0419 (5)
C7	0.4606 (3)	0.14996 (13)	0.88414 (11)	0.0459 (5)
N2	0.6059 (2)	0.50501 (11)	0.85985 (10)	0.0496 (4)
C6	0.2878 (3)	0.13983 (14)	0.87544 (13)	0.0525 (5)
H6	0.2185	0.1891	0.8641	0.063*
C19	0.6367 (3)	0.54269 (13)	0.92942 (12)	0.0475 (5)
C11	−0.1211 (3)	−0.15605 (15)	0.78357 (13)	0.0538 (5)
H11	−0.1607	−0.1626	0.7319	0.065*
C20	0.5772 (3)	0.62678 (14)	0.94207 (14)	0.0585 (6)
H20	0.5992	0.6520	0.9903	0.070*
C3	0.4924 (3)	−0.00607 (14)	0.90999 (12)	0.0511 (5)
H3	0.5614	−0.0553	0.9222	0.061*
C8	0.0992 (3)	−0.12165 (12)	0.88548 (11)	0.0428 (5)
C4	0.2171 (3)	0.05733 (14)	0.88340 (13)	0.0528 (5)
H4	0.1009	0.0508	0.8771	0.063*
C2	0.5622 (3)	0.07580 (14)	0.90102 (11)	0.0491 (5)
H2	0.6784	0.0815	0.9063	0.059*
C9	−0.0083 (3)	−0.13424 (14)	0.93671 (13)	0.0546 (6)
H9	0.0290	−0.1256	0.9883	0.066*
C18	0.7357 (3)	0.48691 (13)	0.98899 (11)	0.0469 (5)
C17	0.7938 (3)	0.51503 (15)	1.06268 (13)	0.0629 (7)
H17	0.7699	0.5720	1.0781	0.075*
N1	0.7676 (2)	0.40440 (11)	0.96637 (9)	0.0468 (4)
C23	0.5176 (3)	0.55082 (16)	0.80230 (13)	0.0628 (6)
H23	0.4968	0.5250	0.7543	0.075*
C22	0.4567 (4)	0.63476 (16)	0.81178 (16)	0.0698 (7)
H22	0.3970	0.6655	0.7708	0.084*
C21	0.4857 (3)	0.67254 (16)	0.88283 (16)	0.0669 (7)
H21	0.4434	0.7287	0.8907	0.080*
C28	−0.2301 (3)	−0.16874 (17)	0.83440 (15)	0.0661 (7)
H28	−0.3419	−0.1833	0.8171	0.079*
C10	−0.1728 (3)	−0.15981 (17)	0.91097 (15)	0.0665 (7)
H10	−0.2448	−0.1710	0.9456	0.080*
C14	0.8592 (3)	0.34967 (16)	1.01506 (13)	0.0585 (6)
H14	0.8819	0.2929	0.9987	0.070*
C15	0.9221 (3)	0.37365 (17)	1.08905 (14)	0.0673 (7)
H15	0.9862	0.3341	1.1219	0.081*
C16	0.8876 (3)	0.45709 (18)	1.11271 (14)	0.0707 (7)
H16	0.9271	0.4748	1.1624	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.05637 (19)	0.04095 (16)	0.04131 (16)	−0.00815 (12)	0.01396 (12)	−0.00735 (11)
O3	0.0553 (9)	0.0445 (8)	0.0490 (8)	−0.0074 (7)	0.0002 (7)	0.0088 (6)
O4	0.0466 (9)	0.0593 (9)	0.0471 (8)	0.0024 (7)	0.0111 (7)	0.0057 (7)
O2	0.0630 (10)	0.0426 (8)	0.0575 (9)	−0.0063 (7)	0.0160 (8)	−0.0051 (7)
C1	0.0598 (14)	0.0461 (12)	0.0383 (11)	−0.0088 (11)	0.0116 (10)	−0.0080 (9)
O5	0.0581 (9)	0.0679 (10)	0.0424 (8)	0.0184 (8)	0.0125 (7)	0.0156 (7)
C13	0.0500 (13)	0.0337 (10)	0.0452 (11)	0.0051 (9)	0.0095 (9)	0.0031 (9)
O1	0.0592 (10)	0.0444 (8)	0.0648 (10)	−0.0096 (7)	0.0185 (8)	−0.0105 (7)
C5	0.0549 (13)	0.0409 (11)	0.0359 (10)	−0.0065 (9)	0.0057 (9)	0.0005 (8)
C12	0.0463 (12)	0.0368 (10)	0.0434 (11)	0.0003 (9)	0.0092 (9)	0.0044 (8)
C7	0.0558 (13)	0.0436 (11)	0.0394 (11)	−0.0088 (10)	0.0109 (10)	−0.0056 (9)
N2	0.0651 (12)	0.0432 (10)	0.0446 (10)	−0.0053 (9)	0.0206 (9)	0.0007 (8)
C6	0.0554 (14)	0.0424 (12)	0.0609 (14)	0.0011 (10)	0.0129 (11)	−0.0002 (10)
C19	0.0591 (13)	0.0380 (11)	0.0510 (12)	−0.0134 (10)	0.0255 (10)	−0.0060 (9)
C11	0.0521 (13)	0.0535 (13)	0.0550 (13)	−0.0055 (11)	0.0060 (11)	0.0034 (11)
C20	0.0708 (16)	0.0427 (12)	0.0689 (15)	−0.0146 (11)	0.0322 (13)	−0.0088 (11)
C3	0.0533 (13)	0.0472 (12)	0.0513 (12)	0.0007 (10)	0.0042 (11)	0.0039 (10)
C8	0.0481 (12)	0.0340 (10)	0.0464 (11)	−0.0018 (9)	0.0082 (9)	0.0056 (8)
C4	0.0484 (13)	0.0482 (12)	0.0622 (13)	−0.0048 (10)	0.0106 (11)	0.0001 (10)
C2	0.0462 (12)	0.0532 (13)	0.0468 (12)	−0.0051 (10)	0.0048 (10)	−0.0022 (10)
C9	0.0691 (16)	0.0515 (13)	0.0458 (12)	0.0029 (11)	0.0174 (11)	0.0056 (10)
C18	0.0570 (13)	0.0422 (11)	0.0452 (11)	−0.0183 (10)	0.0194 (10)	−0.0066 (9)
C17	0.0842 (18)	0.0508 (13)	0.0553 (14)	−0.0278 (13)	0.0166 (13)	−0.0153 (11)
N1	0.0578 (11)	0.0419 (9)	0.0431 (9)	−0.0083 (8)	0.0152 (8)	−0.0044 (8)
C23	0.0838 (18)	0.0583 (14)	0.0496 (13)	0.0027 (13)	0.0204 (12)	0.0066 (11)
C22	0.0818 (18)	0.0579 (15)	0.0749 (18)	0.0059 (13)	0.0287 (15)	0.0217 (13)
C21	0.0783 (18)	0.0431 (13)	0.0880 (19)	−0.0015 (12)	0.0398 (15)	0.0053 (13)
C28	0.0503 (14)	0.0683 (16)	0.0805 (18)	−0.0098 (12)	0.0136 (13)	0.0153 (14)
C10	0.0590 (16)	0.0743 (16)	0.0727 (17)	0.0038 (13)	0.0303 (13)	0.0192 (14)
C14	0.0684 (16)	0.0548 (13)	0.0527 (13)	−0.0021 (12)	0.0109 (12)	−0.0020 (11)
C15	0.0689 (17)	0.0711 (17)	0.0571 (14)	−0.0144 (14)	−0.0036 (13)	0.0055 (12)
C16	0.0867 (19)	0.0711 (17)	0.0506 (14)	−0.0345 (15)	0.0008 (13)	−0.0056 (13)

Geometric parameters (Å, º) top

Ni1—N1	2.0260 (17)	C11—C28	1.376 (3)
Ni1—N2	2.0412 (18)	C11—H11	0.9300
Ni1—O5ⁱ	2.0459 (19)	C20—C21	1.371 (3)
Ni1—O1	2.0694 (16)	C20—H20	0.9300
Ni1—O2	2.1331 (18)	C3—C2	1.374 (3)
Ni1—O4ⁱ	2.1673 (15)	C3—H3	0.9300
O3—C5	1.386 (2)	C8—C9	1.373 (3)
O3—C8	1.389 (3)	C4—H4	0.9300
O4—C13	1.258 (3)	C2—H2	0.9300
O4—Ni1ⁱⁱ	2.1673 (15)	C9—C10	1.384 (3)
O2—C1	1.266 (2)	C9—H9	0.9300
C1—O1	1.264 (3)	C18—N1	1.343 (3)
C1—C7	1.487 (3)	C18—C17	1.388 (3)
O5—C13	1.259 (2)	C17—C16	1.381 (3)
O5—Ni1ⁱⁱ	2.0459 (19)	C17—H17	0.9300
C13—C12	1.490 (3)	N1—C14	1.329 (3)
C13—Ni1ⁱⁱ	2.433 (2)	C23—C22	1.375 (3)
C5—C3	1.370 (3)	C23—H23	0.9300
C5—C4	1.379 (3)	C22—C21	1.374 (4)
C12—C11	1.396 (3)	C22—H22	0.9300
C12—C8	1.397 (3)	C21—H21	0.9300
C7—C6	1.384 (3)	C28—C10	1.375 (3)
C7—C2	1.387 (3)	C28—H28	0.9300
N2—C23	1.340 (3)	C10—H10	0.9300
N2—C19	1.350 (2)	C14—C15	1.382 (3)
C6—C4	1.383 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.367 (3)
C19—C20	1.384 (3)	C15—H15	0.9300
C19—C18	1.480 (3)	C16—H16	0.9300

N1—Ni1—N2	79.66 (7)	C7—C6—H6	119.6
N1—Ni1—O5ⁱ	97.20 (7)	N2—C19—C20	121.2 (2)
N2—Ni1—O5ⁱ	102.16 (7)	N2—C19—C18	114.72 (17)
N1—Ni1—O1	94.92 (6)	C20—C19—C18	124.1 (2)
N2—Ni1—O1	161.32 (7)	C28—C11—C12	121.7 (2)
O5ⁱ—Ni1—O1	96.24 (6)	C28—C11—H11	119.1
N1—Ni1—O2	98.50 (6)	C12—C11—H11	119.1
N2—Ni1—O2	100.10 (7)	C21—C20—C19	119.3 (2)
O5ⁱ—Ni1—O2	154.69 (6)	C21—C20—H20	120.3
O1—Ni1—O2	62.76 (6)	C19—C20—H20	120.3
N1—Ni1—O4ⁱ	158.99 (7)	C5—C3—C2	119.9 (2)
N2—Ni1—O4ⁱ	99.73 (6)	C5—C3—H3	120.0
O5ⁱ—Ni1—O4ⁱ	62.20 (6)	C2—C3—H3	120.0
O1—Ni1—O4ⁱ	91.67 (6)	C9—C8—O3	117.07 (19)
O2—Ni1—O4ⁱ	102.26 (6)	C9—C8—C12	121.8 (2)
N1—Ni1—C1	98.02 (7)	O3—C8—C12	121.12 (19)
N2—Ni1—C1	131.15 (8)	C5—C4—C6	119.1 (2)
O5ⁱ—Ni1—C1	126.32 (7)	C5—C4—H4	120.4
O1—Ni1—C1	31.37 (7)	C6—C4—H4	120.4
O2—Ni1—C1	31.38 (6)	C3—C2—C7	120.5 (2)
O4ⁱ—Ni1—C1	97.98 (6)	C3—C2—H2	119.8
N1—Ni1—C13ⁱ	128.32 (8)	C7—C2—H2	119.8
N2—Ni1—C13ⁱ	103.84 (7)	C8—C9—C10	119.5 (2)
O5ⁱ—Ni1—C13ⁱ	31.15 (6)	C8—C9—H9	120.2
O1—Ni1—C13ⁱ	93.58 (6)	C10—C9—H9	120.2
O2—Ni1—C13ⁱ	130.16 (6)	N1—C18—C17	121.0 (2)
O4ⁱ—Ni1—C13ⁱ	31.08 (6)	N1—C18—C19	114.53 (17)
C1—Ni1—C13ⁱ	114.35 (7)	C17—C18—C19	124.5 (2)
C5—O3—C8	118.40 (15)	C16—C17—C18	119.0 (2)
C13—O4—Ni1ⁱⁱ	86.18 (12)	C16—C17—H17	120.5
C1—O2—Ni1	87.30 (13)	C18—C17—H17	120.5
O1—C1—O2	119.76 (19)	C14—N1—C18	119.28 (19)
O1—C1—C7	118.8 (2)	C14—N1—Ni1	124.68 (15)
O2—C1—C7	121.5 (2)	C18—N1—Ni1	115.90 (14)
O1—C1—Ni1	58.44 (11)	N2—C23—C22	122.2 (2)
O2—C1—Ni1	61.32 (11)	N2—C23—H23	118.9
C7—C1—Ni1	177.03 (17)	C22—C23—H23	118.9
C13—O5—Ni1ⁱⁱ	91.63 (13)	C21—C22—C23	118.9 (2)
O4—C13—O5	119.9 (2)	C21—C22—H22	120.5
O4—C13—C12	122.70 (18)	C23—C22—H22	120.5
O5—C13—C12	117.40 (18)	C20—C21—C22	119.5 (2)
O4—C13—Ni1ⁱⁱ	62.74 (11)	C20—C21—H21	120.3
O5—C13—Ni1ⁱⁱ	57.21 (11)	C22—C21—H21	120.3
C12—C13—Ni1ⁱⁱ	172.74 (15)	C10—C28—C11	119.7 (2)
C1—O1—Ni1	90.19 (13)	C10—C28—H28	120.2
C3—C5—C4	120.79 (19)	C11—C28—H28	120.2
C3—C5—O3	115.13 (18)	C28—C10—C9	120.2 (2)
C4—C5—O3	123.98 (19)	C28—C10—H10	119.9
C11—C12—C8	116.98 (19)	C9—C10—H10	119.9
C11—C12—C13	118.66 (19)	N1—C14—C15	122.7 (2)
C8—C12—C13	124.35 (18)	N1—C14—H14	118.7
C6—C7—C2	118.89 (19)	C15—C14—H14	118.7
C6—C7—C1	122.1 (2)	C16—C15—C14	118.2 (2)
C2—C7—C1	119.0 (2)	C16—C15—H15	120.9
C23—N2—C19	118.88 (19)	C14—C15—H15	120.9
C23—N2—Ni1	125.94 (15)	C15—C16—C17	119.8 (2)
C19—N2—Ni1	114.91 (14)	C15—C16—H16	120.1
C4—C6—C7	120.8 (2)	C17—C16—H16	120.1
C4—C6—H6	119.6

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₈O₅)(C₁₀H₈N₂)]
M_r	471.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.061 (1), 15.039 (2), 17.847 (5)
β (°)	99.464 (3)
V (Å³)	2134.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.764, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	13096, 4938, 3475
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.04
No. of reflections	4938
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N1	2.0260 (17)	Ni1—O1	2.0694 (16)
Ni1—N2	2.0412 (18)	Ni1—O2	2.1331 (18)
Ni1—O5ⁱ	2.0459 (19)	Ni1—O4ⁱ	2.1673 (15)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

We are grateful to Dr Li Bin and Tian Lei for their help during the experiments.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Yang, J., Ma, J. F., Liu, Y. Y. & Batten, S. R. (2009). CrystEngComm, 11, 151–159. Web of Science CSD CrossRef CAS Google Scholar