Bis(2,2'-bipyridine-κN,N')(croconato-κO,O')nickel(II).

The title compound, [Ni(C(5)O(5))(C(10)H(8)N(2))(2)], lies across a crystallographic twofold axis, around which two 2,2'-bipyridine (2,2'-bipy) ligands are arranged in a propeller manner. The local geometry of the NiN(4)O(2) coordination core basically adopts an octa-hedral geometry. The mol-ecular twofold axis is along the direction of the mol-ecular dipole moment, and the complex is packed with its dipole moment alternately along the +b and -b directions. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Chen et al. (2008 ▶). For related structures, see: Chen et al. (2005 ▶, 2007 ▶). For other related literature, see: Coronado et al. (2007 ▶); Wang et al. (2002 ▶).

Experimental

Crystal data

[Ni(C5O5)(C10H8N2)2]

M = 511.13

Orthorhombic,

a = 12.725 (5) Å

b = 10.752 (5) Å

c = 15.733 (5) Å

V = 2152.6 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.95 mm−1

T = 293 (2) K

0.20 × 0.19 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.821, T max = 0.902

10055 measured reflections

2466 independent reflections

1536 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.02

2466 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033771/lx2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033771/lx2071Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C5O5)(C10H8N2)2]	F(000) = 1048
Mr = 511.13	Dx = 1.577 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P_2n 2ab	Cell parameters from 2518 reflections
a = 12.725 (5) Å	θ = 2.5–23.4°
b = 10.752 (5) Å	µ = 0.95 mm−1
c = 15.733 (5) Å	T = 293 K
V = 2152.6 (15) Å3	Prism, green-yellow
Z = 4	0.20 × 0.19 × 0.10 mm

Bruker APEXII CCD diffractometer	2466 independent reflections
Radiation source: fine-focus sealed tube	1536 reflections with I > 2σ(I)
graphite	Rint = 0.089
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.5°
φ and ω scans	h = −15→16
Absorption correction: multi-scan (APEX2; Bruker, 2005)	k = −13→10
Tmin = 0.821, Tmax = 0.902	l = −20→19
10055 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.0108P] where P = (Fo2 + 2Fc2)/3
2466 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.46011 (4)	0.2500	0.03546 (17)
O1	0.56048 (15)	0.31353 (15)	0.17633 (10)	0.0439 (5)
O2	0.6016 (2)	0.0512 (2)	0.12408 (16)	0.1053 (10)
O3	0.5000	−0.1097 (3)	0.2500	0.0700 (9)
N1	0.45364 (18)	0.58822 (19)	0.34037 (12)	0.0397 (5)
N2	0.63184 (17)	0.46676 (19)	0.32573 (12)	0.0419 (6)
C1	0.3650 (3)	0.6535 (3)	0.34092 (17)	0.0531 (8)
H1	0.3173	0.6410	0.2970	0.064*
C2	0.3402 (3)	0.7384 (3)	0.4029 (2)	0.0717 (10)
H2	0.2774	0.7824	0.4013	0.086*
C3	0.4114 (4)	0.7561 (3)	0.4673 (2)	0.0742 (11)
H3	0.3977	0.8142	0.5097	0.089*
C4	0.5025 (3)	0.6888 (3)	0.46926 (18)	0.0570 (9)
H4	0.5502	0.6989	0.5135	0.068*
C5	0.5226 (2)	0.6052 (2)	0.40425 (15)	0.0406 (7)
C6	0.6200 (2)	0.5320 (2)	0.39824 (16)	0.0431 (7)
C7	0.6964 (3)	0.5264 (3)	0.4613 (2)	0.0638 (9)
H7	0.6872	0.5696	0.5119	0.077*
C8	0.7854 (3)	0.4569 (4)	0.4486 (2)	0.0770 (12)
H8	0.8367	0.4526	0.4906	0.092*
C9	0.7982 (2)	0.3940 (3)	0.3737 (2)	0.0679 (10)
H9	0.8587	0.3479	0.3633	0.081*
C10	0.7195 (2)	0.4008 (3)	0.31437 (19)	0.0575 (8)
H10	0.7276	0.3572	0.2637	0.069*
C11	0.5300 (2)	0.2129 (3)	0.21214 (15)	0.0393 (6)
C12	0.5511 (3)	0.0864 (3)	0.18605 (18)	0.0530 (8)
C13	0.5000	0.0035 (4)	0.2500	0.0487 (10)

	U11	U22	U33	U12	U13	U23
Ni1	0.0404 (3)	0.0388 (3)	0.0271 (2)	0.000	−0.0053 (2)	0.000
O1	0.0587 (13)	0.0418 (11)	0.0310 (9)	−0.0040 (10)	0.0083 (9)	0.0013 (8)
O2	0.167 (3)	0.0586 (15)	0.0903 (17)	−0.0026 (15)	0.0769 (19)	−0.0177 (13)
O3	0.086 (2)	0.0405 (17)	0.084 (2)	0.000	0.0118 (18)	0.000
N1	0.0510 (14)	0.0360 (12)	0.0322 (11)	−0.0008 (12)	−0.0020 (11)	0.0015 (10)
N2	0.0437 (14)	0.0480 (14)	0.0340 (12)	0.0003 (12)	−0.0082 (10)	0.0017 (10)
C1	0.064 (2)	0.0507 (18)	0.0443 (16)	0.0138 (17)	0.0003 (16)	0.0011 (14)
C2	0.098 (3)	0.057 (2)	0.060 (2)	0.024 (2)	0.022 (2)	−0.0018 (17)
C3	0.119 (3)	0.048 (2)	0.056 (2)	−0.002 (2)	0.028 (2)	−0.0121 (16)
C4	0.084 (2)	0.0514 (17)	0.0359 (15)	−0.022 (2)	0.0095 (16)	−0.0076 (13)
C5	0.0582 (19)	0.0341 (14)	0.0295 (13)	−0.0130 (14)	0.0012 (12)	0.0026 (11)
C6	0.0535 (18)	0.0442 (16)	0.0317 (14)	−0.0198 (15)	−0.0080 (13)	0.0070 (13)
C7	0.076 (2)	0.068 (2)	0.0482 (18)	−0.023 (2)	−0.0272 (17)	0.0038 (15)
C8	0.065 (2)	0.090 (3)	0.076 (3)	−0.023 (2)	−0.041 (2)	0.033 (2)
C9	0.0442 (18)	0.080 (3)	0.079 (2)	0.0036 (19)	−0.0144 (18)	0.026 (2)
C10	0.0494 (19)	0.067 (2)	0.0555 (19)	0.0078 (18)	−0.0081 (15)	0.0055 (16)
C11	0.0431 (17)	0.0439 (16)	0.0309 (13)	−0.0025 (14)	−0.0005 (11)	−0.0019 (12)
C12	0.066 (2)	0.0462 (17)	0.0463 (17)	−0.0038 (17)	0.0129 (16)	−0.0085 (14)
C13	0.052 (2)	0.042 (2)	0.052 (2)	0.000	0.000 (2)	0.000

Ni1—N2	2.059 (2)	C3—C4	1.367 (4)
Ni1—N2i	2.059 (2)	C3—H3	0.9300
Ni1—N1	2.066 (2)	C4—C5	1.385 (4)
Ni1—N1i	2.066 (2)	C4—H4	0.9300
Ni1—O1i	2.1022 (18)	C5—C6	1.472 (4)
Ni1—O1	2.1022 (18)	C6—C7	1.389 (4)
O1—C11	1.280 (3)	C7—C8	1.371 (5)
O2—C12	1.227 (3)	C7—H7	0.9300
O3—C13	1.217 (5)	C8—C9	1.369 (5)
N1—C1	1.328 (3)	C8—H8	0.9300
N1—C5	1.347 (3)	C9—C10	1.370 (4)
N2—C10	1.334 (3)	C9—H9	0.9300
N2—C6	1.347 (3)	C10—H10	0.9300
C1—C2	1.372 (4)	C11—C11i	1.415 (5)
C1—H1	0.9300	C11—C12	1.446 (4)
C2—C3	1.373 (5)	C12—C13	1.493 (4)
C2—H2	0.9300	C13—C12i	1.493 (4)
N2—Ni1—N2i	176.02 (12)	C3—C4—C5	118.9 (3)
N2—Ni1—N1	79.12 (9)	C3—C4—H4	120.6
N2i—Ni1—N1	98.19 (8)	C5—C4—H4	120.6
N2—Ni1—N1i	98.19 (8)	N1—C5—C4	121.3 (3)
N2i—Ni1—N1i	79.12 (9)	N1—C5—C6	115.4 (2)
N1—Ni1—N1i	96.35 (11)	C4—C5—C6	123.3 (3)
N2—Ni1—O1i	90.30 (8)	N2—C6—C7	120.2 (3)
N2i—Ni1—O1i	92.68 (8)	N2—C6—C5	115.3 (2)
N1—Ni1—O1i	90.91 (8)	C7—C6—C5	124.5 (3)
N1i—Ni1—O1i	169.72 (7)	C8—C7—C6	119.8 (3)
N2—Ni1—O1	92.68 (8)	C8—C7—H7	120.1
N2i—Ni1—O1	90.30 (8)	C6—C7—H7	120.1
N1—Ni1—O1	169.72 (7)	C9—C8—C7	119.5 (3)
N1i—Ni1—O1	90.91 (8)	C9—C8—H8	120.2
O1i—Ni1—O1	82.88 (10)	C7—C8—H8	120.2
C11—O1—Ni1	106.29 (15)	C8—C9—C10	118.2 (3)
C1—N1—C5	118.5 (2)	C8—C9—H9	120.9
C1—N1—Ni1	126.82 (19)	C10—C9—H9	120.9
C5—N1—Ni1	114.72 (18)	N2—C10—C9	123.2 (3)
C10—N2—C6	118.9 (2)	N2—C10—H10	118.4
C10—N2—Ni1	125.83 (19)	C9—C10—H10	118.4
C6—N2—Ni1	114.66 (19)	O1—C11—C11i	122.26 (14)
N1—C1—C2	123.5 (3)	O1—C11—C12	127.9 (2)
N1—C1—H1	118.3	C11i—C11—C12	109.83 (15)
C2—C1—H1	118.3	O2—C12—C11	127.8 (3)
C1—C2—C3	117.7 (3)	O2—C12—C13	125.4 (3)
C1—C2—H2	121.1	C11—C12—C13	106.8 (2)
C3—C2—H2	121.1	O3—C13—C12i	126.64 (17)
C4—C3—C2	120.2 (3)	O3—C13—C12	126.64 (17)
C4—C3—H3	119.9	C12i—C13—C12	106.7 (3)
C2—C3—H3	119.9
N2—Ni1—O1—C11	90.49 (17)	C1—N1—C5—C6	−178.6 (2)
N2i—Ni1—O1—C11	−92.14 (18)	Ni1—N1—C5—C6	1.2 (3)
N1—Ni1—O1—C11	53.7 (5)	C3—C4—C5—N1	−1.0 (4)
N1i—Ni1—O1—C11	−171.27 (17)	C3—C4—C5—C6	177.3 (3)
O1i—Ni1—O1—C11	0.52 (13)	C10—N2—C6—C7	−2.5 (4)
N2—Ni1—N1—C1	174.7 (2)	Ni1—N2—C6—C7	169.1 (2)
N2i—Ni1—N1—C1	−2.3 (2)	C10—N2—C6—C5	178.1 (2)
N1i—Ni1—N1—C1	77.5 (2)	Ni1—N2—C6—C5	−10.3 (3)
O1i—Ni1—N1—C1	−95.2 (2)	N1—C5—C6—N2	6.1 (3)
O1—Ni1—N1—C1	−147.8 (4)	C4—C5—C6—N2	−172.3 (2)
N2—Ni1—N1—C5	−5.04 (17)	N1—C5—C6—C7	−173.3 (2)
N2i—Ni1—N1—C5	177.93 (18)	C4—C5—C6—C7	8.3 (4)
N1i—Ni1—N1—C5	−102.20 (19)	N2—C6—C7—C8	1.8 (4)
O1i—Ni1—N1—C5	85.09 (18)	C5—C6—C7—C8	−178.8 (3)
O1—Ni1—N1—C5	32.5 (5)	C6—C7—C8—C9	0.2 (5)
N1—Ni1—N2—C10	179.3 (2)	C7—C8—C9—C10	−1.5 (5)
N1i—Ni1—N2—C10	−85.7 (2)	C6—N2—C10—C9	1.2 (4)
O1i—Ni1—N2—C10	88.5 (2)	Ni1—N2—C10—C9	−169.4 (2)
O1—Ni1—N2—C10	5.6 (2)	C8—C9—C10—N2	0.8 (5)
N1—Ni1—N2—C6	8.43 (17)	Ni1—O1—C11—C11i	−1.5 (4)
N1i—Ni1—N2—C6	103.37 (17)	Ni1—O1—C11—C12	−179.9 (2)
O1i—Ni1—N2—C6	−82.44 (17)	O1—C11—C12—O2	−0.7 (5)
O1—Ni1—N2—C6	−165.32 (17)	C11i—C11—C12—O2	−179.3 (3)
C5—N1—C1—C2	0.6 (4)	O1—C11—C12—C13	178.9 (2)
Ni1—N1—C1—C2	−179.1 (2)	C11i—C11—C12—C13	0.3 (4)
N1—C1—C2—C3	0.1 (5)	O2—C12—C13—O3	−0.6 (4)
C1—C2—C3—C4	−1.2 (5)	C11—C12—C13—O3	179.89 (13)
C2—C3—C4—C5	1.7 (5)	O2—C12—C13—C12i	179.4 (4)
C1—N1—C5—C4	−0.1 (4)	C11—C12—C13—C12i	−0.11 (13)
Ni1—N1—C5—C4	179.63 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ii	0.93	2.57	3.340 (4)	141
C8—H8···O2iii	0.93	2.24	3.114 (4)	156
C9—H9···O3iv	0.93	2.57	3.222 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.57	3.340 (4)	141
C8—H8⋯O2ii	0.93	2.24	3.114 (4)	156
C9—H9⋯O3iii	0.93	2.57	3.222 (4)	127

Symmetry codes: (i) ; (ii) ; (iii) .