Bis(3-hydroxy-phenyl-acetato-κO,O')bis-(1H-imidazole-κN)nickel(II).

In the title mononuclear complex, [Ni(C(8)H(7)O(3))(2)(C(3)H(4)N(2))(2)], the Ni(II) atom, lying on a twofold rotation axis, is coordinated by four carboxyl-ate O atoms from two bidentate 3-hydroxy-phenylacetato ligands and two N atoms from two imidazole mol-ecules in a distorted octa-hedral geometry. A three-dimensional network is formed via inter-molecular O-H⋯O and N-H⋯O hydrogen bonds and π-π stacking inter-actions between the imidazole and benzene rings of neighboring mol-ecules [centroid-centroid distance = 3.856 (2) Å].

Related literature

For the use of coordination polymers and open framework materials in catalysis, separation, gas storage and molecular recognition, see: James (2003 ▶); Serre et al. (2004 ▶); Yaghi et al. (1998 ▶, 2003 ▶).

Experimental

Crystal data

[Ni(C8H7O3)2(C3H4N2)2]

M = 497.15

Monoclinic,

a = 12.8481 (14) Å

b = 10.6829 (12) Å

c = 16.3051 (19) Å

β = 101.410 (1)°

V = 2193.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.93 mm−1

T = 296 K

0.32 × 0.27 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.762, T max = 0.811

5522 measured reflections

1960 independent reflections

1509 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.094

S = 1.01

1960 reflections

151 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005960/hy2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005960/hy2181Isup2.hkl

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

[Ni(C8H7O3)2(C3H4N2)2]	F(000) = 1032
Mr = 497.15	Dx = 1.505 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5837 reflections
a = 12.8481 (14) Å	θ = 2.8–27.9°
b = 10.6829 (12) Å	µ = 0.93 mm−1
c = 16.3051 (19) Å	T = 296 K
β = 101.410 (1)°	Block, blue
V = 2193.7 (4) Å3	0.32 × 0.27 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	1960 independent reflections
Radiation source: fine-focus sealed tube	1509 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 25.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
Tmin = 0.762, Tmax = 0.811	k = −10→12
5522 measured reflections	l = −19→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0443P)2] where P = (Fo2 + 2Fc2)/3
1960 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.0902 (2)	0.0767 (3)	0.43721 (17)	0.0387 (7)
N1	0.10445 (18)	0.5333 (2)	0.22611 (15)	0.0392 (6)
Ni1	0.0000	0.40576 (5)	0.2500	0.03283 (19)
O1	−0.06407 (15)	0.25890 (17)	0.31434 (12)	0.0421 (5)
C2	0.1936 (2)	0.0654 (3)	0.48209 (18)	0.0438 (8)
H2	0.2208	0.1263	0.5213	0.053*
N2	0.2479 (2)	0.6473 (3)	0.24415 (17)	0.0543 (8)
H2A	0.3104	0.6747	0.2651	0.065*
O2	0.07730 (15)	0.36060 (19)	0.37318 (12)	0.0423 (5)
C3	0.2567 (2)	−0.0347 (3)	0.46956 (19)	0.0451 (8)
O3	0.35853 (19)	−0.0487 (2)	0.51162 (17)	0.0704 (8)
H3	0.3769	0.0141	0.5397	0.106*
C4	0.2166 (3)	−0.1259 (3)	0.4120 (2)	0.0521 (9)
H4	0.2580	−0.1945	0.4040	0.063*
C5	0.1146 (3)	−0.1143 (3)	0.3666 (2)	0.0566 (9)
H5	0.0877	−0.1751	0.3272	0.068*
C6	0.0517 (3)	−0.0144 (3)	0.37856 (19)	0.0503 (8)
H6	−0.0169	−0.0079	0.3472	0.060*
C7	0.0230 (3)	0.1885 (3)	0.45013 (18)	0.0476 (8)
H7A	−0.0462	0.1602	0.4578	0.057*
H7B	0.0565	0.2332	0.5002	0.057*
C8	0.0100 (2)	0.2748 (3)	0.37584 (17)	0.0369 (7)
C9	0.1992 (2)	0.5532 (3)	0.2722 (2)	0.0534 (9)
H9	0.2283	0.5060	0.3191	0.064*
C10	0.0930 (3)	0.6207 (3)	0.1660 (2)	0.0586 (10)
H10	0.0335	0.6304	0.1236	0.070*
C11	0.1815 (3)	0.6928 (4)	0.1766 (2)	0.0699 (11)
H11	0.1939	0.7602	0.1437	0.084*

	U11	U22	U33	U12	U13	U23
C1	0.0439 (19)	0.0382 (18)	0.0339 (16)	0.0014 (14)	0.0076 (14)	0.0093 (14)
N1	0.0313 (14)	0.0370 (14)	0.0487 (16)	−0.0043 (11)	0.0066 (12)	−0.0007 (12)
Ni1	0.0233 (3)	0.0304 (3)	0.0417 (3)	0.000	−0.0010 (2)	0.000
O1	0.0325 (11)	0.0430 (12)	0.0454 (12)	−0.0088 (9)	−0.0050 (10)	0.0045 (10)
C2	0.055 (2)	0.0348 (18)	0.0385 (17)	−0.0029 (14)	0.0013 (16)	−0.0036 (13)
N2	0.0370 (16)	0.0630 (19)	0.0620 (19)	−0.0242 (14)	0.0077 (14)	−0.0082 (15)
O2	0.0316 (11)	0.0438 (12)	0.0458 (12)	−0.0053 (10)	−0.0060 (10)	−0.0007 (10)
C3	0.0437 (19)	0.0416 (18)	0.0447 (18)	0.0013 (15)	−0.0042 (15)	−0.0026 (15)
O3	0.0543 (15)	0.0611 (16)	0.0821 (19)	0.0126 (13)	−0.0195 (14)	−0.0175 (14)
C4	0.054 (2)	0.0443 (19)	0.053 (2)	0.0052 (16)	0.0004 (18)	−0.0078 (16)
C5	0.062 (2)	0.050 (2)	0.054 (2)	−0.0066 (17)	0.0004 (18)	−0.0176 (16)
C6	0.0437 (19)	0.056 (2)	0.047 (2)	−0.0042 (16)	−0.0015 (16)	−0.0030 (17)
C7	0.053 (2)	0.050 (2)	0.0401 (18)	0.0095 (16)	0.0090 (16)	0.0049 (15)
C8	0.0316 (17)	0.0367 (17)	0.0404 (17)	0.0035 (13)	0.0023 (14)	−0.0021 (13)
C9	0.0348 (18)	0.054 (2)	0.066 (2)	−0.0085 (16)	−0.0027 (17)	0.0087 (18)
C10	0.054 (2)	0.069 (3)	0.046 (2)	−0.0209 (18)	−0.0041 (17)	0.0133 (18)
C11	0.080 (3)	0.070 (3)	0.057 (2)	−0.036 (2)	0.006 (2)	0.010 (2)

C1—C6	1.385 (4)	O2—C8	1.267 (3)
C1—C2	1.389 (4)	C3—O3	1.360 (3)
C1—C7	1.513 (4)	C3—C4	1.380 (4)
N1—C9	1.315 (4)	O3—H3	0.8200
N1—C10	1.340 (4)	C4—C5	1.378 (4)
Ni1—N1	2.004 (2)	C4—H4	0.9300
Ni1—N1i	2.004 (2)	C5—C6	1.376 (4)
Ni1—O2i	2.1128 (19)	C5—H5	0.9300
Ni1—O2	2.1128 (19)	C6—H6	0.9300
Ni1—O1i	2.1404 (18)	C7—C8	1.505 (4)
Ni1—O1	2.1404 (18)	C7—H7A	0.9700
O1—C8	1.250 (3)	C7—H7B	0.9700
C2—C3	1.381 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.356 (4)
N2—C9	1.313 (4)	C10—H10	0.9300
N2—C11	1.343 (4)	C11—H11	0.9300
N2—H2A	0.8600
C6—C1—C2	118.5 (3)	C11—N2—H2A	126.5
C6—C1—C7	121.0 (3)	C8—O2—Ni1	90.11 (16)
C2—C1—C7	120.5 (3)	O3—C3—C2	123.0 (3)
C9—N1—C10	105.1 (3)	O3—C3—C4	117.2 (3)
C9—N1—Ni1	125.3 (2)	C2—C3—C4	119.8 (3)
C10—N1—Ni1	129.4 (2)	C3—O3—H3	109.5
N1—Ni1—N1i	94.31 (13)	C5—C4—C3	119.3 (3)
N1—Ni1—O2i	100.22 (9)	C5—C4—H4	120.4
N1i—Ni1—O2i	97.65 (9)	C3—C4—H4	120.4
N1—Ni1—O2	97.65 (9)	C6—C5—C4	121.1 (3)
N1i—Ni1—O2	100.22 (9)	C6—C5—H5	119.4
O2i—Ni1—O2	153.60 (11)	C4—C5—H5	119.4
N1—Ni1—O1i	93.78 (8)	C5—C6—C1	120.2 (3)
N1i—Ni1—O1i	158.58 (9)	C5—C6—H6	119.9
O2i—Ni1—O1i	61.36 (7)	C1—C6—H6	119.9
O2—Ni1—O1i	98.31 (8)	C8—C7—C1	110.3 (2)
N1—Ni1—O1	158.58 (9)	C8—C7—H7A	109.6
N1i—Ni1—O1	93.78 (8)	C1—C7—H7A	109.6
O2i—Ni1—O1	98.31 (8)	C8—C7—H7B	109.6
O2—Ni1—O1	61.36 (7)	C1—C7—H7B	109.6
O1i—Ni1—O1	85.73 (10)	H7A—C7—H7B	108.1
N1—Ni1—C8i	98.66 (9)	O1—C8—O2	119.2 (3)
N1i—Ni1—C8i	128.39 (10)	O1—C8—C7	120.5 (3)
O2i—Ni1—C8i	30.92 (8)	O2—C8—C7	120.2 (3)
O2—Ni1—C8i	126.79 (9)	N2—C9—N1	112.0 (3)
O1i—Ni1—C8i	30.45 (8)	N2—C9—H9	124.0
O1—Ni1—C8i	91.74 (8)	N1—C9—H9	124.0
C8—O1—Ni1	89.31 (17)	N1—C10—C11	109.5 (3)
C3—C2—C1	121.2 (3)	N1—C10—H10	125.2
C3—C2—H2	119.4	C11—C10—H10	125.2
C1—C2—H2	119.4	N2—C11—C10	106.2 (3)
C9—N2—C11	107.1 (3)	N2—C11—H11	126.9
C9—N2—H2A	126.5	C10—C11—H11	126.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ii	0.86	1.88	2.734 (3)	171
O3—H3···O2iii	0.82	1.96	2.763 (3)	168

Table 1

Selected bond lengths (Å)

Ni1—N1	2.004 (2)
Ni1—O2	2.1128 (19)
Ni1—O1	2.1404 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	1.88	2.734 (3)	171
O3—H3⋯O2ii	0.82	1.96	2.763 (3)	168

Symmetry codes: (i) ; (ii) .