metal-organic compounds
catena-Poly[[[diaquadiformatonickel(II)]-μ-1,4-bis(1H-benzimidazol-1-yl)benzene] dihydrate]
aDepartment of Applied Chemistry, Yuncheng University, Yuncheng, Shanxi 044000, People's Republic of China
*Correspondence e-mail: lihuiwff@163.com
In the title one-dimensional coordination polymer, {[Ni(CHO2)2(C20H14N4)(H2O)2]·2H2O}n, the NiII atom lies on a crystallographic inversion centre. It is coordinated by two formate O atoms, two water O atoms and two N atoms from two 1,4-bis(1H-benzimidazol-1-yl)benzene (bzb) ligands, resulting in a distorted trans-NiN2O4 octahedral coordination geometry. The bzb molecule acts as a bridging ligand to connect the metal atoms into a chain propagating in [1]. The dihedral angle between the benzimidazole ring and the central benzene ring in the ligand is 38.16 (9)°. In the crystal, O—H⋯O hydrogen bonds crosslink the chains into (010) sheets.
Related literature
For background to coordination polymers containing imidazole-derived ligands, see: Li et al. (2009, 2011).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; 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.
Supporting information
10.1107/S160053681200284X/hb6604sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681200284X/hb6604Isup2.hkl
A mixture of CH3OH and H2O (1:1, 8 ml), as a buffer layer, was carefully layered over a solution of Ni(HCO2)2 in H2O (6 ml). Then a solution of 1,4-di(1H-benzimidazol-1-yl)benzene (L, 0.06 mmol) in CH3OH (6 ml) was layered over the buffer layer, and the resultant reaction was left to stand at room temperature. After ca three weeks, green block single crystals appeared at the boundary. Yield: ~20% (based on L).
C-bound H atoms were positioned geometrically and refined in the riding-model approximation, with C—H = 0.93Å and Uiso(H) = 1.2Ueq (C).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius. | |
Fig. 2. The crystal packing for (I). |
[Ni(CHO2)2(C20H14N4)(H2O)2]·2H2O | Z = 1 |
Mr = 531.16 | F(000) = 276 |
Triclinic, P1 | Dx = 1.548 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4431 (15) Å | Cell parameters from 6111 reflections |
b = 9.0895 (18) Å | θ = 6.2–55.0° |
c = 9.3863 (19) Å | µ = 0.91 mm−1 |
α = 78.46 (3)° | T = 293 K |
β = 77.79 (3)° | Block, green |
γ = 67.86 (3)° | 0.25 × 0.22 × 0.20 mm |
V = 569.8 (2) Å3 |
Rigaku Mercury CCD diffractometer | 2000 independent reflections |
Radiation source: fine-focus sealed tube | 1874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 3.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −10→10 |
Tmin = 0.797, Tmax = 0.834 | l = −11→11 |
5022 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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0208P)2 + 0.3422P] where P = (Fo2 + 2Fc2)/3 |
2000 reflections | (Δ/σ)max < 0.001 |
160 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
[Ni(CHO2)2(C20H14N4)(H2O)2]·2H2O | γ = 67.86 (3)° |
Mr = 531.16 | V = 569.8 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.4431 (15) Å | Mo Kα radiation |
b = 9.0895 (18) Å | µ = 0.91 mm−1 |
c = 9.3863 (19) Å | T = 293 K |
α = 78.46 (3)° | 0.25 × 0.22 × 0.20 mm |
β = 77.79 (3)° |
Rigaku Mercury CCD diffractometer | 2000 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 1874 reflections with I > 2σ(I) |
Tmin = 0.797, Tmax = 0.834 | Rint = 0.021 |
5022 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.23 e Å−3 |
2000 reflections | Δρmin = −0.19 e Å−3 |
160 parameters |
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 | 1.0000 | 0.0000 | 0.0000 | 0.01789 (11) | |
N1 | 0.8599 (2) | 0.05059 (18) | 0.21160 (16) | 0.0233 (4) | |
N2 | 0.7076 (2) | 0.21017 (19) | 0.38522 (17) | 0.0251 (4) | |
O1 | 1.11753 (19) | 0.17566 (16) | −0.00983 (15) | 0.0272 (3) | |
O2 | 1.3775 (2) | 0.24681 (19) | −0.03883 (19) | 0.0439 (4) | |
O2W | 0.8143 (3) | 0.4708 (2) | 0.9185 (2) | 0.0580 (5) | |
O1W | 0.76721 (19) | 0.18582 (16) | −0.09086 (15) | 0.0265 (3) | |
C1 | 0.7822 (3) | 0.1980 (2) | 0.2416 (2) | 0.0265 (4) | |
H1 | 0.7785 | 0.2864 | 0.1709 | 0.032* | |
C2 | 0.7415 (3) | 0.0544 (2) | 0.4562 (2) | 0.0243 (4) | |
C3 | 0.6960 (3) | −0.0069 (3) | 0.6010 (2) | 0.0349 (5) | |
H3 | 0.6319 | 0.0598 | 0.6733 | 0.042* | |
C4 | 0.7496 (4) | −0.1702 (3) | 0.6330 (2) | 0.0410 (6) | |
H4 | 0.7235 | −0.2156 | 0.7294 | 0.049* | |
C5 | 0.8426 (3) | −0.2698 (3) | 0.5238 (3) | 0.0390 (5) | |
H5 | 0.8762 | −0.3800 | 0.5493 | 0.047* | |
C6 | 0.8858 (3) | −0.2091 (2) | 0.3798 (2) | 0.0301 (5) | |
H6 | 0.9465 | −0.2762 | 0.3076 | 0.036* | |
C7 | 0.8359 (3) | −0.0440 (2) | 0.3458 (2) | 0.0223 (4) | |
C8 | 0.6026 (3) | 0.3572 (2) | 0.4442 (2) | 0.0242 (4) | |
C9 | 0.6216 (3) | 0.3723 (2) | 0.5828 (2) | 0.0280 (5) | |
H9 | 0.7031 | 0.2864 | 0.6386 | 0.034* | |
C10 | 0.5193 (3) | 0.5154 (2) | 0.6388 (2) | 0.0292 (5) | |
H10 | 0.5321 | 0.5262 | 0.7322 | 0.035* | |
C11 | 1.2948 (3) | 0.1551 (2) | −0.0493 (2) | 0.0280 (5) | |
H11 | 1.3723 | 0.0622 | −0.0905 | 0.034* | |
H1A | 0.6479 | 0.1921 | −0.0709 | 0.042* | |
H1B | 0.7658 | 0.2799 | −0.0905 | 0.042* | |
H2A | 0.7644 | 0.5582 | 0.9559 | 0.042* | |
H2B | 0.9293 | 0.4212 | 0.9405 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01748 (19) | 0.01802 (19) | 0.01746 (19) | −0.00478 (14) | 0.00105 (13) | −0.00749 (13) |
N1 | 0.0272 (9) | 0.0210 (9) | 0.0184 (8) | −0.0052 (7) | 0.0011 (7) | −0.0064 (7) |
N2 | 0.0323 (9) | 0.0199 (8) | 0.0185 (8) | −0.0045 (7) | 0.0018 (7) | −0.0073 (6) |
O1 | 0.0218 (7) | 0.0261 (8) | 0.0348 (8) | −0.0090 (6) | 0.0019 (6) | −0.0117 (6) |
O2 | 0.0276 (8) | 0.0366 (9) | 0.0723 (12) | −0.0153 (7) | −0.0012 (8) | −0.0161 (8) |
O2W | 0.0580 (12) | 0.0302 (9) | 0.0900 (15) | −0.0068 (8) | −0.0309 (10) | −0.0132 (9) |
O1W | 0.0220 (7) | 0.0249 (7) | 0.0311 (8) | −0.0061 (6) | −0.0041 (6) | −0.0041 (6) |
C1 | 0.0348 (11) | 0.0218 (10) | 0.0185 (10) | −0.0068 (9) | 0.0017 (8) | −0.0052 (8) |
C2 | 0.0247 (10) | 0.0217 (10) | 0.0230 (10) | −0.0043 (8) | 0.0000 (8) | −0.0067 (8) |
C3 | 0.0440 (13) | 0.0329 (12) | 0.0215 (11) | −0.0100 (10) | 0.0042 (9) | −0.0063 (9) |
C4 | 0.0539 (15) | 0.0345 (13) | 0.0257 (12) | −0.0133 (11) | 0.0021 (10) | 0.0031 (9) |
C5 | 0.0459 (14) | 0.0235 (11) | 0.0397 (13) | −0.0089 (10) | 0.0003 (10) | 0.0002 (9) |
C6 | 0.0308 (11) | 0.0234 (11) | 0.0311 (12) | −0.0045 (9) | 0.0016 (9) | −0.0091 (9) |
C7 | 0.0209 (10) | 0.0218 (10) | 0.0221 (10) | −0.0044 (8) | −0.0010 (8) | −0.0068 (8) |
C8 | 0.0267 (10) | 0.0217 (10) | 0.0207 (10) | −0.0047 (8) | 0.0021 (8) | −0.0087 (8) |
C9 | 0.0321 (11) | 0.0234 (10) | 0.0238 (11) | −0.0020 (9) | −0.0065 (8) | −0.0059 (8) |
C10 | 0.0378 (12) | 0.0290 (11) | 0.0186 (10) | −0.0061 (9) | −0.0038 (8) | −0.0097 (8) |
C11 | 0.0241 (11) | 0.0248 (11) | 0.0333 (12) | −0.0057 (9) | −0.0026 (9) | −0.0075 (9) |
Ni1—O1i | 2.0695 (14) | C2—C3 | 1.385 (3) |
Ni1—O1 | 2.0695 (14) | C2—C7 | 1.399 (3) |
Ni1—N1i | 2.0908 (16) | C3—C4 | 1.371 (3) |
Ni1—N1 | 2.0908 (16) | C3—H3 | 0.9300 |
Ni1—O1W | 2.1036 (16) | C4—C5 | 1.395 (3) |
Ni1—O1Wi | 2.1036 (16) | C4—H4 | 0.9300 |
N1—C1 | 1.307 (2) | C5—C6 | 1.373 (3) |
N1—C7 | 1.395 (2) | C5—H5 | 0.9300 |
N2—C1 | 1.354 (2) | C6—C7 | 1.389 (3) |
N2—C2 | 1.391 (2) | C6—H6 | 0.9300 |
N2—C8 | 1.424 (2) | C8—C9 | 1.377 (3) |
O1—C11 | 1.245 (2) | C8—C10ii | 1.385 (3) |
O2—C11 | 1.236 (2) | C9—C10 | 1.380 (3) |
O2W—H2A | 0.8522 | C9—H9 | 0.9300 |
O2W—H2B | 0.8516 | C10—C8ii | 1.385 (3) |
O1W—H1A | 0.8504 | C10—H10 | 0.9300 |
O1W—H1B | 0.8516 | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | ||
O1i—Ni1—O1 | 180.00 (5) | C3—C2—C7 | 122.24 (18) |
O1i—Ni1—N1i | 87.66 (6) | N2—C2—C7 | 105.25 (16) |
O1—Ni1—N1i | 92.34 (6) | C4—C3—C2 | 116.98 (19) |
O1i—Ni1—N1 | 92.34 (6) | C4—C3—H3 | 121.5 |
O1—Ni1—N1 | 87.66 (6) | C2—C3—H3 | 121.5 |
N1i—Ni1—N1 | 180.00 (10) | C3—C4—C5 | 121.4 (2) |
O1i—Ni1—O1W | 94.56 (6) | C3—C4—H4 | 119.3 |
O1—Ni1—O1W | 85.44 (6) | C5—C4—H4 | 119.3 |
N1i—Ni1—O1W | 89.72 (6) | C6—C5—C4 | 121.7 (2) |
N1—Ni1—O1W | 90.28 (6) | C6—C5—H5 | 119.2 |
O1i—Ni1—O1Wi | 85.44 (6) | C4—C5—H5 | 119.2 |
O1—Ni1—O1Wi | 94.56 (6) | C5—C6—C7 | 117.75 (19) |
N1i—Ni1—O1Wi | 90.28 (6) | C5—C6—H6 | 121.1 |
N1—Ni1—O1Wi | 89.72 (6) | C7—C6—H6 | 121.1 |
O1W—Ni1—O1Wi | 180.00 (11) | C6—C7—N1 | 130.60 (17) |
C1—N1—C7 | 105.03 (15) | C6—C7—C2 | 119.93 (18) |
C1—N1—Ni1 | 120.95 (13) | N1—C7—C2 | 109.45 (16) |
C7—N1—Ni1 | 133.87 (12) | C9—C8—C10ii | 120.26 (18) |
C1—N2—C2 | 106.47 (16) | C9—C8—N2 | 120.29 (18) |
C1—N2—C8 | 124.79 (17) | C10ii—C8—N2 | 119.45 (17) |
C2—N2—C8 | 128.57 (16) | C8—C9—C10 | 119.76 (19) |
C11—O1—Ni1 | 123.29 (13) | C8—C9—H9 | 120.1 |
H2A—O2W—H2B | 109.0 | C10—C9—H9 | 120.1 |
Ni1—O1W—H1A | 124.7 | C9—C10—C8ii | 119.98 (18) |
Ni1—O1W—H1B | 114.7 | C9—C10—H10 | 120.0 |
H1A—O1W—H1B | 105.8 | C8ii—C10—H10 | 120.0 |
N1—C1—N2 | 113.79 (18) | O2—C11—O1 | 126.04 (19) |
N1—C1—H1 | 123.1 | O2—C11—H11 | 117.0 |
N2—C1—H1 | 123.1 | O1—C11—H11 | 117.0 |
C3—C2—N2 | 132.49 (18) | ||
O1i—Ni1—N1—C1 | −139.94 (16) | N2—C2—C3—C4 | 178.9 (2) |
O1—Ni1—N1—C1 | 40.06 (16) | C7—C2—C3—C4 | 0.7 (3) |
N1i—Ni1—N1—C1 | 152 (100) | C2—C3—C4—C5 | −1.2 (4) |
O1W—Ni1—N1—C1 | −45.36 (16) | C3—C4—C5—C6 | 0.4 (4) |
O1Wi—Ni1—N1—C1 | 134.64 (16) | C4—C5—C6—C7 | 0.8 (3) |
O1i—Ni1—N1—C7 | 45.25 (18) | C5—C6—C7—N1 | −179.6 (2) |
O1—Ni1—N1—C7 | −134.75 (18) | C5—C6—C7—C2 | −1.2 (3) |
N1i—Ni1—N1—C7 | −23 (100) | C1—N1—C7—C6 | 178.2 (2) |
O1W—Ni1—N1—C7 | 139.83 (18) | Ni1—N1—C7—C6 | −6.4 (3) |
O1Wi—Ni1—N1—C7 | −40.17 (18) | C1—N1—C7—C2 | −0.3 (2) |
O1i—Ni1—O1—C11 | 90 (100) | Ni1—N1—C7—C2 | 175.08 (14) |
N1i—Ni1—O1—C11 | −48.98 (16) | C3—C2—C7—C6 | 0.5 (3) |
N1—Ni1—O1—C11 | 131.02 (16) | N2—C2—C7—C6 | −178.12 (18) |
O1W—Ni1—O1—C11 | −138.51 (16) | C3—C2—C7—N1 | 179.16 (19) |
O1Wi—Ni1—O1—C11 | 41.49 (16) | N2—C2—C7—N1 | 0.6 (2) |
C7—N1—C1—N2 | −0.1 (2) | C1—N2—C8—C9 | −145.1 (2) |
Ni1—N1—C1—N2 | −176.23 (13) | C2—N2—C8—C9 | 40.3 (3) |
C2—N2—C1—N1 | 0.5 (2) | C1—N2—C8—C10ii | 35.2 (3) |
C8—N2—C1—N1 | −175.17 (18) | C2—N2—C8—C10ii | −139.5 (2) |
C1—N2—C2—C3 | −179.0 (2) | C10ii—C8—C9—C10 | −0.3 (3) |
C8—N2—C2—C3 | −3.6 (4) | N2—C8—C9—C10 | 179.95 (18) |
C1—N2—C2—C7 | −0.6 (2) | C8—C9—C10—C8ii | 0.3 (3) |
C8—N2—C2—C7 | 174.80 (18) | Ni1—O1—C11—O2 | −169.69 (16) |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2iii | 0.85 | 1.85 | 2.694 (2) | 169 |
O1W—H1B···O2Wiv | 0.85 | 1.92 | 2.762 (2) | 169 |
O2W—H2A···O2v | 0.85 | 1.91 | 2.760 (2) | 173 |
O2W—H2B···O1vi | 0.85 | 2.16 | 2.846 (2) | 137 |
Symmetry codes: (iii) x−1, y, z; (iv) x, y, z−1; (v) −x+2, −y+1, −z+1; (vi) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(CHO2)2(C20H14N4)(H2O)2]·2H2O |
Mr | 531.16 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.4431 (15), 9.0895 (18), 9.3863 (19) |
α, β, γ (°) | 78.46 (3), 77.79 (3), 67.86 (3) |
V (Å3) | 569.8 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.25 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Rigaku Mercury CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.797, 0.834 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5022, 2000, 1874 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.061, 1.09 |
No. of reflections | 2000 |
No. of parameters | 160 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.19 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2i | 0.85 | 1.85 | 2.694 (2) | 169 |
O1W—H1B···O2Wii | 0.85 | 1.92 | 2.762 (2) | 169 |
O2W—H2A···O2iii | 0.85 | 1.91 | 2.760 (2) | 173 |
O2W—H2B···O1iv | 0.85 | 2.16 | 2.846 (2) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) x, y, z−1; (iii) −x+2, −y+1, −z+1; (iv) x, y, z+1. |
Acknowledgements
The authors thank the Young Scientist Fund of the NSFC of China (grant No. 51101138) and the College Research Program of Yuncheng University (grant No. 2008114) for funding.
References
Li, Z. X., Chu, X., Cui, G. H., Liu, Y., Li, L. & Xue, G. L. (2011). CrystEngComm, 13, 1984–1989. Web of Science CSD CrossRef CAS Google Scholar
Li, Z. X., Xu, Y., Zuo, Y., Li, L., Pan, Q., Hu, T. L. & Bu, X. H. (2009). Cryst. Growth Des. 9, 3904–3909. Web of Science CSD CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Imidazole has been extensively used in crystal engineering, and a large number of imidazole-containing flexible ligands have been extensively studied. However, to our knowledge, the research on imidazole ligands bearing rigid spacers is still less developed (Li et al., 2009; Li et al., 2011). For the title compound, the geometry of the NiII ion is bound by two benzimidazole rings of individual L ligands, two water molecules and two formate ions forming a slightly distorted octahedral coordination environment(Fig. 1). Notably, as shown in Fig. 2, the six-coordinate NiII center is bridged by the ligand L to form an infinite one-dimensional architecture.