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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.094
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          1

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    --  O1      ..       5.08 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    --  O2      ..       7.46 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    --  O4_b    ..       7.62 su
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         36

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

Hydrogen atoms were included in calculated positions and refined on their parent atoms with C—H distances of 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

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

	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]

Crystal data

[Ni(C14H8O5)(C10H8N2)]	F(000) = 968
Mr = 471.10	Dx = 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) Å^3	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 0.1348P] where P = (Fo^2 + 2Fc^2)/3
4938 reflections	(Δ/σ)max = 0.002
289 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Ni1—N1	2.0260 (17)	C11—C28	1.376 (3)
Ni1—N2	2.0412 (18)	C11—H11	0.9300
Ni1—O5^i	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—O4^i	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—Ni1^ii	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—Ni1^ii	2.0459 (19)	C17—H17	0.9300
C13—C12	1.490 (3)	N1—C14	1.329 (3)
C13—Ni1^ii	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—O5^i	97.20 (7)	N2—C19—C20	121.2 (2)
N2—Ni1—O5^i	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)
O5^i—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)
O5^i—Ni1—O2	154.69 (6)	C21—C20—H20	120.3
O1—Ni1—O2	62.76 (6)	C19—C20—H20	120.3
N1—Ni1—O4^i	158.99 (7)	C5—C3—C2	119.9 (2)
N2—Ni1—O4^i	99.73 (6)	C5—C3—H3	120.0
O5^i—Ni1—O4^i	62.20 (6)	C2—C3—H3	120.0
O1—Ni1—O4^i	91.67 (6)	C9—C8—O3	117.07 (19)
O2—Ni1—O4^i	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)
O5^i—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)
O4^i—Ni1—C1	97.98 (6)	C3—C2—H2	119.8
N1—Ni1—C13^i	128.32 (8)	C7—C2—H2	119.8
N2—Ni1—C13^i	103.84 (7)	C8—C9—C10	119.5 (2)
O5^i—Ni1—C13^i	31.15 (6)	C8—C9—H9	120.2
O1—Ni1—C13^i	93.58 (6)	C10—C9—H9	120.2
O2—Ni1—C13^i	130.16 (6)	N1—C18—C17	121.0 (2)
O4^i—Ni1—C13^i	31.08 (6)	N1—C18—C19	114.53 (17)
C1—Ni1—C13^i	114.35 (7)	C17—C18—C19	124.5 (2)
C5—O3—C8	118.40 (15)	C16—C17—C18	119.0 (2)
C13—O4—Ni1^ii	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—Ni1^ii	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—Ni1^ii	62.74 (11)	C20—C21—H21	120.3
O5—C13—Ni1^ii	57.21 (11)	C22—C21—H21	120.3
C12—C13—Ni1^ii	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.