catena-Poly[[bis-[3-(1H-imidazol-1-yl)-1-phenyl-propan-1-one-κN]nickel(II)]-μ-oxalato-κO,O:O,O].

In the title compound, [Ni(C(2)O(4))(C(12)H(12)N(2)O)(2)](n), the Ni(II) atom, lying on a twofold rotation axis, is coordinated by two N atoms from two monodentate 3-(1H-imidazol-1-yl)-1-phenyl-propan-1-one (L) ligands and four O atoms from two oxalate anions in a distorted octa-hedral geometry. The oxalate anion has a twofold rotation axis through the mid-point of the C-C bond and acts as a bridging ligand, linking the Ni(II) atoms into a polymeric chain along [010]. Weak inter-molecular C-H⋯O hydrogen bonds connect the chains, resulting in a three-dimensional supra-molecular structure. >

Related literature

For background to the construction of metal-organic frameworks using a mixed-ligand strategy, see: Du et al. (2005 ▶); Tao et al. (2000 ▶); Ye et al. (2005 ▶).

Experimental

Crystal data

[Ni(C2O4)(C12H12N2O)2]

M = 547.20

Monoclinic,

a = 15.3065 (11) Å

b = 5.6605 (4) Å

c = 27.536 (2) Å

β = 95.613 (1)°

V = 2374.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.87 mm−1

T = 296 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.793, T max = 0.845

5794 measured reflections

2105 independent reflections

1676 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.096

S = 1.02

2105 reflections

168 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.45 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: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049646/hy2488sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049646/hy2488Isup2.hkl

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

[Ni(C2O4)(C12H12N2O)2]	F(000) = 1136
Mr = 547.20	Dx = 1.531 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1107 reflections
a = 15.3065 (11) Å	θ = 2.9–21.3°
b = 5.6605 (4) Å	µ = 0.87 mm−1
c = 27.536 (2) Å	T = 296 K
β = 95.613 (1)°	Block, colorless
V = 2374.3 (3) Å3	0.28 × 0.22 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	2105 independent reflections
Radiation source: fine-focus sealed tube	1676 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
Tmin = 0.793, Tmax = 0.845	k = −6→5
5794 measured reflections	l = −32→32

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0315P)2 + 4.5895P] where P = (Fo2 + 2Fc2)/3
2105 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.63 e Å−3
1 restraint	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq
Ni1	0.5000	−0.13748 (10)	0.7500	0.02887 (19)
O1	0.46495 (16)	0.1678 (4)	0.79304 (9)	0.0464 (6)
O2	0.46148 (17)	0.5597 (5)	0.79161 (9)	0.0528 (7)
O3	0.8709 (3)	0.4212 (6)	0.93819 (12)	0.0912 (12)
N1	0.62123 (18)	−0.1330 (5)	0.78683 (10)	0.0388 (7)
N2	0.73701 (18)	−0.0047 (5)	0.83297 (10)	0.0400 (7)
C1	0.6893 (2)	−0.2891 (6)	0.78450 (13)	0.0418 (9)
H1	0.6865	−0.4274	0.7662	0.050*
C2	0.6534 (2)	0.0357 (7)	0.81664 (12)	0.0421 (9)
H2	0.6216	0.1666	0.8252	0.050*
C3	0.7610 (2)	−0.2127 (7)	0.81268 (13)	0.0433 (9)
H3	0.8155	−0.2863	0.8173	0.052*
C4	0.7933 (2)	0.1504 (7)	0.86521 (13)	0.0497 (10)
H4A	0.7668	0.3059	0.8657	0.060*
H4B	0.8499	0.1668	0.8525	0.060*
C5	0.8066 (3)	0.0541 (8)	0.91673 (13)	0.0591 (12)
H5A	0.7498	0.0192	0.9279	0.071*
H5B	0.8394	−0.0925	0.9166	0.071*
C6	0.8547 (3)	0.2235 (9)	0.95153 (15)	0.0573 (11)
C7	0.8814 (3)	0.1443 (9)	1.00249 (14)	0.0572 (11)
C8	0.8604 (4)	−0.0672 (11)	1.02023 (18)	0.099 (2)
H8	0.8268	−0.1721	1.0002	0.119*
C9	0.8881 (5)	−0.1321 (11)	1.06808 (19)	0.115 (2)
H9	0.8725	−0.2788	1.0797	0.138*
C10	0.9371 (3)	0.0151 (11)	1.09733 (17)	0.0782 (15)
H10	0.9546	−0.0283	1.1294	0.094*
C11	0.9609 (4)	0.2238 (12)	1.08058 (18)	0.0918 (18)
H11	0.9964	0.3247	1.1006	0.110*
C12	0.9326 (4)	0.2895 (10)	1.03341 (16)	0.0855 (17)
H12	0.9488	0.4367	1.0222	0.103*
C13	0.4784 (2)	0.3633 (6)	0.77433 (12)	0.0357 (8)

	U11	U22	U33	U12	U13	U23
Ni1	0.0301 (3)	0.0254 (3)	0.0291 (3)	0.000	−0.0074 (2)	0.000
O1	0.0468 (15)	0.0402 (14)	0.0522 (15)	0.0059 (12)	0.0044 (12)	0.0031 (11)
O2	0.0515 (16)	0.0561 (18)	0.0480 (16)	0.0131 (13)	−0.0091 (13)	−0.0136 (13)
O3	0.125 (3)	0.075 (3)	0.066 (2)	−0.038 (2)	−0.027 (2)	0.0008 (18)
N1	0.0409 (17)	0.0349 (16)	0.0391 (16)	0.0020 (14)	−0.0034 (13)	−0.0032 (14)
N2	0.0357 (17)	0.0447 (18)	0.0372 (16)	0.0003 (14)	−0.0086 (13)	−0.0031 (15)
C1	0.042 (2)	0.040 (2)	0.042 (2)	0.0066 (17)	0.0002 (17)	−0.0078 (17)
C2	0.039 (2)	0.043 (2)	0.041 (2)	0.0053 (17)	−0.0081 (17)	−0.0050 (18)
C3	0.033 (2)	0.048 (2)	0.048 (2)	0.0055 (17)	−0.0039 (17)	0.0025 (18)
C4	0.045 (2)	0.055 (2)	0.046 (2)	−0.008 (2)	−0.0118 (18)	−0.006 (2)
C5	0.065 (3)	0.060 (3)	0.048 (2)	−0.011 (2)	−0.017 (2)	−0.002 (2)
C6	0.056 (3)	0.067 (3)	0.046 (2)	−0.008 (2)	−0.007 (2)	−0.005 (2)
C7	0.053 (2)	0.073 (3)	0.042 (2)	−0.010 (2)	−0.0081 (19)	−0.010 (2)
C8	0.133 (5)	0.095 (4)	0.060 (3)	−0.046 (4)	−0.035 (3)	0.004 (3)
C9	0.169 (6)	0.106 (5)	0.062 (3)	−0.048 (5)	−0.038 (4)	0.019 (3)
C10	0.077 (3)	0.109 (4)	0.046 (3)	0.002 (3)	−0.010 (3)	−0.008 (3)
C11	0.084 (4)	0.134 (5)	0.053 (3)	−0.036 (4)	−0.014 (3)	−0.015 (3)
C12	0.093 (4)	0.110 (4)	0.050 (3)	−0.042 (3)	−0.010 (3)	−0.009 (3)
C13	0.0311 (18)	0.0335 (19)	0.0402 (19)	0.0031 (16)	−0.0089 (15)	0.0039 (17)

Ni1—N1	2.026 (3)	C4—H4A	0.9700
Ni1—N1i	2.026 (3)	C4—H4B	0.9700
Ni1—O2ii	2.175 (3)	C5—C6	1.497 (5)
Ni1—O2iii	2.175 (3)	C5—H5A	0.9700
Ni1—O1	2.191 (3)	C5—H5B	0.9700
Ni1—O1i	2.191 (3)	C6—C7	1.492 (6)
O1—C13	1.247 (4)	C7—C8	1.344 (7)
O2—C13	1.247 (4)	C7—C12	1.372 (6)
O3—C6	1.211 (5)	C8—C9	1.393 (7)
N1—C2	1.322 (4)	C8—H8	0.9300
N1—C1	1.372 (4)	C9—C10	1.337 (7)
N2—C2	1.334 (4)	C9—H9	0.9300
N2—C3	1.369 (4)	C10—C11	1.332 (7)
N2—C4	1.467 (4)	C10—H10	0.9300
C1—C3	1.352 (5)	C11—C12	1.380 (6)
C1—H1	0.9300	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—H3	0.9300	C13—C13i	1.550 (7)
C4—C5	1.515 (5)
N1—Ni1—N1i	178.56 (17)	C5—C4—H4A	109.3
N1—Ni1—O2ii	89.51 (10)	N2—C4—H4B	109.3
N1i—Ni1—O2ii	91.63 (11)	C5—C4—H4B	109.3
N1—Ni1—O2iii	91.63 (11)	H4A—C4—H4B	108.0
N1i—Ni1—O2iii	89.51 (11)	C6—C5—C4	112.4 (4)
O2ii—Ni1—O2iii	75.98 (14)	C6—C5—H5A	109.1
N1—Ni1—O1	88.86 (10)	C4—C5—H5A	109.1
N1i—Ni1—O1	90.01 (11)	C6—C5—H5B	109.1
O2ii—Ni1—O1	178.36 (9)	C4—C5—H5B	109.1
O2iii—Ni1—O1	104.07 (9)	H5A—C5—H5B	107.8
N1—Ni1—O1i	90.01 (11)	O3—C6—C7	121.2 (4)
N1i—Ni1—O1i	88.86 (10)	O3—C6—C5	120.0 (4)
O2ii—Ni1—O1i	104.07 (9)	C7—C6—C5	118.8 (4)
O2iii—Ni1—O1i	178.36 (9)	C8—C7—C12	116.8 (4)
O1—Ni1—O1i	75.92 (13)	C8—C7—C6	123.8 (4)
C13—O1—Ni1	114.7 (2)	C12—C7—C6	119.4 (5)
C13—O2—Ni1iv	115.1 (2)	C7—C8—C9	121.1 (5)
C2—N1—C1	104.8 (3)	C7—C8—H8	119.4
C2—N1—Ni1	125.9 (2)	C9—C8—H8	119.4
C1—N1—Ni1	129.1 (2)	C10—C9—C8	120.4 (6)
C2—N2—C3	107.3 (3)	C10—C9—H9	119.8
C2—N2—C4	126.1 (3)	C8—C9—H9	119.8
C3—N2—C4	126.6 (3)	C11—C10—C9	120.0 (5)
C3—C1—N1	110.2 (3)	C11—C10—H10	120.0
C3—C1—H1	124.9	C9—C10—H10	120.0
N1—C1—H1	124.9	C10—C11—C12	119.6 (5)
N1—C2—N2	111.8 (3)	C10—C11—H11	120.2
N1—C2—H2	124.1	C12—C11—H11	120.2
N2—C2—H2	124.1	C7—C12—C11	122.0 (5)
C1—C3—N2	105.9 (3)	C7—C12—H12	119.0
C1—C3—H3	127.0	C11—C12—H12	119.0
N2—C3—H3	127.0	O2—C13—O1	125.8 (3)
N2—C4—C5	111.6 (3)	O2—C13—C13i	116.9 (2)
N2—C4—H4A	109.3	O1—C13—C13i	117.3 (2)
N1—Ni1—O1—C13	91.5 (2)	C2—N2—C4—C5	105.2 (4)
N1i—Ni1—O1—C13	−87.6 (2)	C3—N2—C4—C5	−77.3 (5)
O2iii—Ni1—O1—C13	−177.1 (2)	N2—C4—C5—C6	−173.1 (3)
O1i—Ni1—O1—C13	1.18 (18)	C4—C5—C6—O3	7.0 (7)
O2ii—Ni1—N1—C2	170.1 (3)	C4—C5—C6—C7	−173.5 (4)
O2iii—Ni1—N1—C2	−114.0 (3)	O3—C6—C7—C8	175.5 (5)
O1—Ni1—N1—C2	−9.9 (3)	C5—C6—C7—C8	−4.0 (7)
O1i—Ni1—N1—C2	66.0 (3)	O3—C6—C7—C12	−6.5 (7)
O2ii—Ni1—N1—C1	−5.1 (3)	C5—C6—C7—C12	173.9 (5)
O2iii—Ni1—N1—C1	70.8 (3)	C12—C7—C8—C9	1.3 (9)
O1—Ni1—N1—C1	174.9 (3)	C6—C7—C8—C9	179.3 (6)
O1i—Ni1—N1—C1	−109.2 (3)	C7—C8—C9—C10	−0.6 (11)
C2—N1—C1—C3	−0.1 (4)	C8—C9—C10—C11	−1.0 (10)
Ni1—N1—C1—C3	175.9 (2)	C9—C10—C11—C12	1.8 (9)
C1—N1—C2—N2	0.1 (4)	C8—C7—C12—C11	−0.5 (9)
Ni1—N1—C2—N2	−176.0 (2)	C6—C7—C12—C11	−178.6 (5)
C3—N2—C2—N1	−0.1 (4)	C10—C11—C12—C7	−1.1 (9)
C4—N2—C2—N1	177.8 (3)	Ni1iv—O2—C13—O1	177.3 (3)
N1—C1—C3—N2	0.0 (4)	Ni1iv—O2—C13—C13i	−1.6 (4)
C2—N2—C3—C1	0.1 (4)	Ni1—O1—C13—O2	178.1 (3)
C4—N2—C3—C1	−177.8 (3)	Ni1—O1—C13—C13i	−3.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1v	0.93	2.46	3.290 (4)	149
C4—H4B···O2v	0.97	2.58	3.467 (5)	152
C10—H10···O2vi	0.93	2.42	3.318 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.46	3.290 (4)	149
C4—H4B⋯O2i	0.97	2.58	3.467 (5)	152
C10—H10⋯O2ii	0.93	2.42	3.318 (5)	162

Symmetry codes: (i) ; (ii) .