Tetra-μ-benzoato-κO:O'-bis-[(benzoic acid-κO)nickel(II)].

The title compound, [Ni(2)(C(7)H(5)O(2))(4)(C(7)H(6)O(2))(2)], is composed of two Ni(II) ions, four bridging benzoate anions and two η(1)-benzoic acid mol-ecules. The [Ni(2)(PhCOO)(4)] unit adopts a typical paddle-wheel conformation. The center between the two Ni(II) atoms represents a crystallographic center of inversion. In addition, each Ni(II) ion also coordinates to one O atom from a benzoic acid mol-ecule. The crystal packing is realised by inter-molecular hydrogen-bonding inter-actions and π-π stacking inter-actions, with a centroid-centroid distance of 3.921 (1) Å.

Related literature

For related benzoate complexes, see: Cotton et al. (2005 ▶, 1987 ▶, 1988 ▶); Bellitto et al. (1985 ▶); Figuerola et al. (2007 ▶); Gavrilenko et al. (2008 ▶); Shi et al. (2004 ▶); Zheng et al. (2004 ▶); Zhong et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

[Ni2(C7H5O2)4(C7H6O2)2]

M = 846.10

Monoclinic,

a = 10.7685 (8) Å

b = 11.7173 (7) Å

c = 15.258 (1) Å

β = 91.354 (3)°

V = 1924.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 273 K

0.28 × 0.26 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.759, T max = 0.819

17534 measured reflections

4639 independent reflections

3789 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.055

S = 0.99

4639 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044766/im2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044766/im2153Isup2.hkl

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

[Ni2(C7H5O2)4(C7H6O2)2]	F(000) = 872
Mr = 846.10	Dx = 1.460 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7941 reflections
a = 10.7685 (8) Å	θ = 2.3–28.0°
b = 11.7173 (7) Å	µ = 1.04 mm−1
c = 15.258 (1) Å	T = 273 K
β = 91.354 (3)°	Block, blue
V = 1924.7 (2) Å3	0.28 × 0.26 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	4639 independent reflections
Radiation source: fine-focus sealed tube	3789 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 28.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −14→12
Tmin = 0.759, Tmax = 0.819	k = −15→14
17534 measured reflections	l = −18→20

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + 1.1987P] where P = (Fo2 + 2Fc2)/3
4639 reflections	(Δ/σ)max = 0.002
254 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.517820 (18)	0.106516 (17)	0.979210 (13)	0.03259 (6)
O1	0.42315 (11)	−0.11994 (11)	0.89928 (7)	0.0471 (3)
O2	0.45485 (12)	0.06289 (11)	0.86345 (8)	0.0499 (3)
O3	0.31459 (11)	−0.05001 (10)	1.05426 (8)	0.0473 (3)
O4	0.34725 (11)	0.13053 (10)	1.01561 (8)	0.0483 (3)
O5	0.56860 (12)	0.28015 (11)	0.94023 (9)	0.0528 (3)
O6	0.75910 (14)	0.25119 (13)	0.89184 (13)	0.0800 (5)
H6	0.7451	0.1858	0.9080	0.120*
C1	0.27981 (15)	0.05301 (15)	1.04542 (10)	0.0397 (4)
C2	0.15133 (15)	0.08413 (16)	1.07061 (11)	0.0428 (4)
C3	0.07758 (19)	0.0110 (2)	1.11745 (14)	0.0656 (6)
H3	0.1080	−0.0598	1.1353	0.079*
C4	−0.0418 (2)	0.0433 (2)	1.13776 (17)	0.0817 (7)
H4	−0.0910	−0.0053	1.1704	0.098*
C5	−0.0880 (2)	0.1463 (2)	1.11020 (17)	0.0768 (7)
H5	−0.1690	0.1667	1.1230	0.092*
C6	−0.0157 (2)	0.2189 (2)	1.06420 (18)	0.0779 (7)
H6A	−0.0472	0.2889	1.0456	0.093*
C7	0.10426 (18)	0.18862 (18)	1.04522 (15)	0.0623 (6)
H7	0.1540	0.2393	1.0149	0.075*
C8	0.41868 (15)	−0.03704 (15)	0.84671 (11)	0.0402 (4)
C9	0.36303 (15)	−0.05843 (16)	0.75772 (11)	0.0429 (4)
C10	0.34030 (19)	0.03208 (18)	0.70105 (12)	0.0567 (5)
H10	0.3640	0.1056	0.7170	0.068*
C11	0.2822 (2)	0.0125 (2)	0.62069 (14)	0.0708 (6)
H11	0.2670	0.0731	0.5826	0.085*
C12	0.2468 (2)	−0.0961 (2)	0.59682 (14)	0.0715 (6)
H12	0.2077	−0.1087	0.5427	0.086*
C13	0.2689 (2)	−0.1858 (2)	0.65259 (14)	0.0710 (6)
H13	0.2442	−0.2591	0.6365	0.085*
C14	0.32799 (19)	−0.16738 (18)	0.73287 (12)	0.0564 (5)
H14	0.3442	−0.2286	0.7702	0.068*
C15	0.66085 (18)	0.31531 (16)	0.90494 (12)	0.0464 (4)
C16	0.67474 (18)	0.43389 (16)	0.87387 (12)	0.0470 (4)
C17	0.5774 (2)	0.50892 (17)	0.88474 (13)	0.0563 (5)
H17	0.5048	0.4842	0.9105	0.068*
C18	0.5882 (2)	0.62111 (19)	0.85726 (14)	0.0684 (6)
H18	0.5231	0.6720	0.8651	0.082*
C19	0.6951 (3)	0.6569 (2)	0.81847 (15)	0.0758 (7)
H19	0.7021	0.7323	0.8000	0.091*
C20	0.7914 (3)	0.5829 (2)	0.80675 (17)	0.0809 (7)
H20	0.8631	0.6077	0.7798	0.097*
C21	0.7825 (2)	0.47092 (19)	0.83488 (15)	0.0670 (6)
H21	0.8484	0.4208	0.8277	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.03193 (10)	0.03109 (10)	0.03470 (10)	0.00072 (9)	−0.00051 (7)	0.00127 (9)
O1	0.0553 (7)	0.0457 (7)	0.0400 (6)	−0.0009 (6)	−0.0056 (5)	−0.0001 (6)
O2	0.0593 (8)	0.0479 (7)	0.0420 (7)	−0.0071 (6)	−0.0089 (6)	0.0007 (6)
O3	0.0406 (7)	0.0409 (7)	0.0607 (8)	0.0068 (6)	0.0076 (6)	0.0041 (6)
O4	0.0381 (6)	0.0430 (7)	0.0640 (8)	0.0051 (6)	0.0062 (6)	0.0046 (6)
O5	0.0531 (8)	0.0408 (7)	0.0648 (8)	0.0010 (6)	0.0111 (6)	0.0076 (6)
O6	0.0642 (10)	0.0483 (9)	0.1289 (15)	0.0090 (8)	0.0353 (9)	0.0193 (9)
C1	0.0377 (9)	0.0440 (10)	0.0373 (9)	0.0044 (8)	−0.0017 (7)	−0.0025 (7)
C2	0.0347 (9)	0.0493 (11)	0.0443 (9)	0.0041 (8)	0.0010 (7)	−0.0063 (8)
C3	0.0504 (12)	0.0710 (15)	0.0759 (15)	0.0086 (11)	0.0157 (10)	0.0131 (12)
C4	0.0524 (14)	0.094 (2)	0.1000 (19)	0.0019 (13)	0.0287 (13)	0.0100 (16)
C5	0.0427 (12)	0.0887 (19)	0.0995 (19)	0.0124 (12)	0.0143 (12)	−0.0141 (15)
C6	0.0511 (13)	0.0690 (16)	0.114 (2)	0.0214 (12)	0.0130 (13)	0.0013 (14)
C7	0.0466 (11)	0.0550 (13)	0.0860 (15)	0.0113 (10)	0.0142 (10)	0.0041 (11)
C8	0.0348 (9)	0.0466 (10)	0.0393 (9)	0.0026 (8)	0.0013 (7)	−0.0023 (8)
C9	0.0380 (9)	0.0526 (11)	0.0381 (9)	−0.0003 (8)	−0.0004 (7)	−0.0031 (8)
C10	0.0632 (13)	0.0571 (13)	0.0493 (11)	−0.0062 (10)	−0.0107 (9)	0.0030 (9)
C11	0.0832 (16)	0.0773 (16)	0.0508 (12)	0.0016 (13)	−0.0206 (11)	0.0083 (11)
C12	0.0783 (16)	0.0869 (18)	0.0483 (12)	0.0023 (14)	−0.0214 (11)	−0.0103 (12)
C13	0.0864 (17)	0.0681 (15)	0.0578 (13)	−0.0087 (13)	−0.0151 (12)	−0.0166 (11)
C14	0.0677 (13)	0.0549 (12)	0.0463 (10)	−0.0010 (10)	−0.0069 (9)	−0.0046 (9)
C15	0.0518 (11)	0.0414 (10)	0.0460 (10)	0.0004 (9)	0.0013 (8)	−0.0009 (8)
C16	0.0575 (11)	0.0395 (10)	0.0441 (10)	−0.0042 (9)	−0.0002 (8)	−0.0006 (8)
C17	0.0650 (13)	0.0499 (12)	0.0539 (12)	0.0032 (10)	−0.0006 (10)	0.0029 (9)
C18	0.0915 (17)	0.0472 (13)	0.0662 (14)	0.0111 (12)	−0.0076 (12)	0.0016 (10)
C19	0.112 (2)	0.0447 (13)	0.0706 (15)	−0.0124 (14)	−0.0019 (14)	0.0078 (11)
C20	0.0904 (19)	0.0598 (16)	0.0932 (18)	−0.0205 (14)	0.0171 (15)	0.0114 (13)
C21	0.0697 (15)	0.0512 (13)	0.0808 (15)	−0.0051 (11)	0.0141 (12)	0.0040 (11)

Ni1—O2	1.9452 (12)	C7—H7	0.9300
Ni1—O4	1.9519 (12)	C8—C9	1.492 (2)
Ni1—O1i	1.9520 (11)	C9—C14	1.382 (3)
Ni1—O3i	1.9999 (12)	C9—C10	1.386 (3)
Ni1—O5	2.1926 (13)	C10—C11	1.382 (3)
Ni1—Ni1i	2.6062 (4)	C10—H10	0.9300
O1—C8	1.260 (2)	C11—C12	1.375 (3)
O1—Ni1i	1.9520 (11)	C11—H11	0.9300
O2—C8	1.258 (2)	C12—C13	1.370 (3)
O3—C1	1.270 (2)	C12—H12	0.9300
O3—Ni1i	1.9999 (12)	C13—C14	1.384 (3)
O4—C1	1.255 (2)	C13—H13	0.9300
O5—C15	1.213 (2)	C14—H14	0.9300
O6—C15	1.317 (2)	C15—C16	1.477 (3)
O6—H6	0.8200	C16—C17	1.381 (3)
C1—C2	1.490 (2)	C16—C21	1.386 (3)
C2—C3	1.379 (3)	C17—C18	1.385 (3)
C2—C7	1.377 (3)	C17—H17	0.9300
C3—C4	1.382 (3)	C18—C19	1.373 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.368 (3)	C19—C20	1.367 (3)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.359 (3)	C20—C21	1.384 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.377 (3)	C21—H21	0.9300
C6—H6A	0.9300
O2—Ni1—O4	89.20 (5)	O2—C8—O1	125.54 (16)
O2—Ni1—O1i	169.19 (5)	O2—C8—C9	117.17 (16)
O4—Ni1—O1i	90.32 (5)	O1—C8—C9	117.27 (16)
O2—Ni1—O3i	88.77 (5)	C14—C9—C10	119.50 (17)
O4—Ni1—O3i	168.91 (5)	C14—C9—C8	120.40 (17)
O1i—Ni1—O3i	89.64 (5)	C10—C9—C8	120.01 (17)
O2—Ni1—O5	94.67 (5)	C11—C10—C9	119.7 (2)
O4—Ni1—O5	100.71 (5)	C11—C10—H10	120.1
O1i—Ni1—O5	96.03 (5)	C9—C10—H10	120.1
O3i—Ni1—O5	90.32 (5)	C12—C11—C10	120.4 (2)
O2—Ni1—Ni1i	85.36 (4)	C12—C11—H11	119.8
O4—Ni1—Ni1i	85.63 (4)	C10—C11—H11	119.8
O1i—Ni1—Ni1i	83.83 (4)	C13—C12—C11	120.16 (19)
O3i—Ni1—Ni1i	83.34 (4)	C13—C12—H12	119.9
O5—Ni1—Ni1i	173.66 (4)	C11—C12—H12	119.9
C8—O1—Ni1i	123.31 (11)	C12—C13—C14	120.0 (2)
C8—O2—Ni1	121.90 (11)	C12—C13—H13	120.0
C1—O3—Ni1i	123.58 (11)	C14—C13—H13	120.0
C1—O4—Ni1	123.73 (11)	C13—C14—C9	120.3 (2)
C15—O5—Ni1	130.36 (12)	C13—C14—H14	119.9
C15—O6—H6	109.5	C9—C14—H14	119.9
O4—C1—O3	123.69 (15)	O5—C15—O6	122.89 (17)
O4—C1—C2	117.72 (15)	O5—C15—C16	123.51 (18)
O3—C1—C2	118.58 (16)	O6—C15—C16	113.59 (17)
C3—C2—C7	119.05 (17)	C17—C16—C21	119.83 (19)
C3—C2—C1	122.08 (17)	C17—C16—C15	118.53 (18)
C7—C2—C1	118.87 (17)	C21—C16—C15	121.64 (18)
C2—C3—C4	119.7 (2)	C16—C17—C18	119.9 (2)
C2—C3—H3	120.1	C16—C17—H17	120.0
C4—C3—H3	120.1	C18—C17—H17	120.0
C5—C4—C3	120.4 (2)	C19—C18—C17	119.8 (2)
C5—C4—H4	119.8	C19—C18—H18	120.1
C3—C4—H4	119.8	C17—C18—H18	120.1
C6—C5—C4	120.1 (2)	C18—C19—C20	120.6 (2)
C6—C5—H5	119.9	C18—C19—H19	119.7
C4—C5—H5	119.9	C20—C19—H19	119.7
C5—C6—C7	119.9 (2)	C19—C20—C21	120.2 (2)
C5—C6—H6A	120.0	C19—C20—H20	119.9
C7—C6—H6A	120.0	C21—C20—H20	119.9
C6—C7—C2	120.7 (2)	C20—C21—C16	119.7 (2)
C6—C7—H7	119.6	C20—C21—H21	120.2
C2—C7—H7	119.6	C16—C21—H21	120.2

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O3i	0.82	1.81	2.626 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O3i	0.82	1.81	2.626 (2)	170

Symmetry code: (i) .