supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, m1547    [ doi:10.1107/S1600536808036866 ]

catena-Poly[[diaqua(2,2'-bipyridine-[kappa]2N,N')nickel(II)]-[mu]-biphenyl-2,2'-dicarboxylato-[kappa]2O:O']

Z. An and X.-C. Niu

Abstract top

In the title compound, [Ni(C14H8O4)(C10H8N2)(H2O)2]n, the NiII atom is coordinated in a slightly distorted octahedral geometry by two water molecules, two N atoms from a 2,2'-bipyridine ligand and two O atoms from the carboxylate groups of two 2,2'-biphenyldicarboxylate (2,2'-dpa) ligands. The 2,2'-dpa ligand acts as a bridge between neighbouring NiII atoms, forming one-dimensional coordination polymers along [100]. The coordinated water molecules form hydrogen bonds to the carboxylate O atoms of 2,2'-dpa within the same coordination polymer, and one O-H...[pi] interaction is also formed to 2,2'-dpa.

Comment top

2,2'-Biphenyldicarboxylic acid (H2dpa) has been demonstrated to be a useful ligand for constructing metal-organic frameworks (Rueff et al., 2003; Wang et al., 2006; Xu et al., 2006). The title compound is a NiII coordination polymer in which 2,2'-biphenyldicarboxylate (2,2'-dpa) acts as a bridging ligand.

The asymmetric unit (Fig. 1) contains one NiII atom coordinated by one 2,2'-bipyridine ligand, 2,2'-dpa and two water molecules. The NiII atom is hexacoordinated in a slightly distorted octahedral geometry by two water molecules, two N atoms from 2,2'-bipyridine, and two O atoms from carboxylate groups of two 2,2'-dpa. The 2,2'-dpa ligand acts as a bridge to link two neighboring NiII atoms, forming a 1-D coordination polymer along [100] (Fig. 2). Hydrogen bonds from the coordinated water molecules and the O atoms of the carboxylate groups are formed within the same coordination polymer (Fig. 3). One water molecule also forms an O—H···πi interaction to the neighbouring benzene ring of 2,2'-dpa.

Related literature top

For other metal–organic frameworks containing 2,2'-dpa, see: Rueff et al. (2003); Wang et al. (2006); Xu et al. (2006).

Experimental top

A mixture of nickel(II) chloride hexahydrate (0.1 mmol), 2,2'-bipyridine (0.1 mmol), biphenyl-2,2'-dicarboxylic acid (0.2 mmol) and H2O (16 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 463 K for five days. Green crystals were obtained after cooling to room temperature with a yield of 12%. Elemental analysis calculated: C 58.64, H 4.89, N 5.70%; found: C 58.62, H 4.86, N 5.65%.

Refinement top

H atoms of the water molecules were located from difference Fourier maps and refined freely with Uiso(H) = 1.2Ueq(O). All other H atoms were placed in calculated positions with C—H = 0.93 Å and allowed to ride with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound showing displacement ellipsoids at 30% for non-H atoms.
[Figure 2] Fig. 2. 1-D coordination polymer running along the [100] direction.
[Figure 3] Fig. 3. View of the packing along the a axis.
catena-Poly[[diaqua(2,2'-bipyridine-κ2N,N')nickel(II)]- µ-biphenyl-2,2'-dicarboxylato-κ2O:O'] top
Crystal data top
[Ni(C14H8O4)(C10H8N2)(H2O)2]F(000) = 1016
Mr = 491.11Dx = 1.471 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3953 reflections
a = 10.9087 (15) Åθ = 2.1–25.1°
b = 11.214 (2) ŵ = 0.92 mm−1
c = 18.129 (3) ÅT = 296 K
V = 2217.6 (6) Å3Block, green
Z = 40.42 × 0.27 × 0.19 mm
Data collection top
Bruker APEXII CCD
diffractometer		3953 independent reflections
Radiation source: fine-focus sealed tube3351 reflections with I > 2σ(I)
graphiteRint = 0.033
φ and ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −13→12
Tmin = 0.699, Tmax = 0.845k = −9→13
11746 measured reflectionsl = −20→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.051P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3953 reflectionsΔρmax = 0.21 e Å−3
310 parametersΔρmin = −0.30 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1694 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.042 (16)
Crystal data top
[Ni(C14H8O4)(C10H8N2)(H2O)2]V = 2217.6 (6) Å3
Mr = 491.11Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.9087 (15) ŵ = 0.92 mm−1
b = 11.214 (2) ÅT = 296 K
c = 18.129 (3) Å0.42 × 0.27 × 0.19 mm
Data collection top
Bruker APEXII CCD
diffractometer		3953 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3351 reflections with I > 2σ(I)
Tmin = 0.699, Tmax = 0.845Rint = 0.033
11746 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088Δρmax = 0.21 e Å−3
S = 1.00Δρmin = −0.30 e Å−3
3953 reflectionsAbsolute structure: Flack (1983), 1694 Friedel pairs
310 parametersFlack parameter: 0.042 (16)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.24756 (4)0.69154 (3)0.898676 (19)0.03527 (12)
C10.5625 (3)1.0010 (3)1.06148 (16)0.0367 (7)
C20.4305 (3)1.0354 (3)1.03948 (16)0.0377 (8)
C30.4167 (4)1.1232 (3)0.98610 (18)0.0525 (9)
H30.48641.15820.96610.063*
C40.3031 (5)1.1602 (4)0.9617 (2)0.0673 (14)
H40.29771.21880.92550.081*
C50.1971 (4)1.1108 (4)0.9905 (2)0.0616 (12)
H50.12081.13530.97350.074*
C60.2059 (3)1.0243 (3)1.04525 (19)0.0515 (10)
H60.13510.99181.06560.062*
C70.3233 (3)0.9853 (3)1.07010 (16)0.0386 (8)
C80.3257 (3)0.9030 (3)1.13631 (16)0.0360 (7)
C90.3102 (3)0.9525 (3)1.20745 (18)0.0492 (9)
H90.29881.03451.21100.059*
C100.3108 (4)0.8874 (4)1.27158 (19)0.0552 (10)
H100.29540.92391.31670.066*
C110.3343 (4)0.7687 (4)1.26763 (18)0.0553 (10)
H110.33830.72221.31010.066*
C120.3524 (3)0.7181 (3)1.19772 (17)0.0469 (8)
H120.37060.63721.19500.056*
C130.3445 (3)0.7820 (3)1.13252 (16)0.0356 (7)
C140.3500 (3)0.7168 (3)1.05824 (16)0.0342 (7)
C150.4937 (3)0.8346 (3)0.8927 (2)0.0509 (9)
H150.49580.82240.94350.061*
C160.5799 (3)0.9085 (3)0.8606 (2)0.0608 (10)
H160.63920.94570.88940.073*
C170.5771 (4)0.9267 (4)0.7847 (3)0.0678 (12)
H170.63370.97720.76250.081*
C180.4900 (4)0.8695 (4)0.7424 (2)0.0596 (10)
H180.48770.88020.69150.071*
C190.4047 (3)0.7949 (3)0.77769 (18)0.0401 (7)
C200.3066 (3)0.7286 (3)0.73743 (17)0.0383 (8)
C210.3005 (4)0.7230 (3)0.65934 (18)0.0527 (10)
H210.35950.76090.63060.063*
C220.2058 (4)0.6605 (3)0.6264 (2)0.0587 (11)
H220.20070.65550.57530.070*
C230.1192 (4)0.6058 (3)0.66986 (18)0.0525 (10)
H230.05470.56380.64860.063*
C240.1297 (3)0.6143 (3)0.74713 (18)0.0451 (8)
H240.07050.57800.77640.054*
N10.4065 (2)0.7797 (2)0.85219 (14)0.0402 (7)
N20.2231 (2)0.6733 (2)0.78055 (13)0.0363 (6)
O10.28142 (19)0.75413 (19)1.00612 (11)0.0407 (6)
O20.4185 (2)0.6272 (2)1.05422 (12)0.0451 (6)
O30.58196 (19)0.89368 (18)1.07528 (12)0.0385 (5)
O40.6422 (2)1.0789 (2)1.06222 (17)0.0670 (8)
O50.1519 (2)0.85857 (18)0.89069 (12)0.0394 (5)
H1W0.187 (2)0.895 (3)0.9264 (15)0.047*
H2W0.0764 (16)0.858 (3)0.9025 (17)0.047*
O60.3552 (2)0.5345 (2)0.91659 (13)0.0466 (6)
H3W0.302 (3)0.484 (3)0.9225 (18)0.056*
H4W0.385 (3)0.557 (3)0.9558 (13)0.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0390 (2)0.0344 (2)0.0325 (2)−0.0010 (2)0.0015 (2)−0.00163 (16)
C10.047 (2)0.0325 (18)0.0310 (16)0.0033 (16)0.0056 (14)0.0009 (14)
C20.058 (2)0.0275 (16)0.0275 (15)0.0093 (16)−0.0028 (15)−0.0034 (13)
C30.080 (3)0.0377 (19)0.0401 (19)0.006 (2)−0.0049 (19)0.0003 (17)
C40.114 (4)0.042 (2)0.045 (2)0.026 (2)−0.033 (2)−0.0035 (18)
C50.080 (3)0.049 (2)0.056 (2)0.034 (2)−0.032 (2)−0.015 (2)
C60.054 (2)0.052 (2)0.048 (2)0.0185 (18)−0.0131 (16)−0.0215 (18)
C70.049 (2)0.0350 (18)0.0319 (16)0.0132 (15)−0.0035 (15)−0.0093 (14)
C80.0320 (17)0.0416 (18)0.0343 (16)0.0010 (14)0.0026 (14)−0.0022 (14)
C90.056 (2)0.046 (2)0.045 (2)0.0093 (17)0.0060 (17)−0.0082 (17)
C100.065 (2)0.068 (3)0.0335 (18)−0.004 (2)0.0110 (17)−0.0084 (18)
C110.071 (3)0.065 (3)0.0296 (17)−0.011 (2)0.0051 (18)0.0021 (17)
C120.059 (2)0.0417 (19)0.0402 (18)−0.0088 (17)−0.0019 (17)0.0041 (16)
C130.0349 (17)0.0436 (19)0.0283 (15)−0.0034 (15)0.0040 (13)−0.0020 (14)
C140.0370 (17)0.0334 (18)0.0321 (16)−0.0062 (15)0.0009 (14)−0.0021 (14)
C150.0413 (19)0.054 (2)0.057 (2)−0.0117 (16)0.0082 (18)−0.0048 (19)
C160.043 (2)0.053 (2)0.087 (3)−0.0107 (19)0.007 (2)−0.002 (2)
C170.048 (2)0.054 (2)0.102 (3)−0.013 (2)0.015 (2)0.019 (2)
C180.061 (2)0.056 (2)0.062 (2)−0.002 (2)0.016 (2)0.018 (2)
C190.0407 (17)0.0313 (17)0.0482 (19)0.0054 (15)0.0106 (15)0.0042 (15)
C200.0513 (19)0.0280 (16)0.0356 (17)0.0079 (15)0.0065 (15)0.0024 (14)
C210.078 (3)0.043 (2)0.0376 (18)0.0082 (19)0.0099 (18)0.0045 (16)
C220.096 (3)0.050 (2)0.0305 (17)0.018 (2)−0.0062 (19)0.0007 (17)
C230.072 (3)0.041 (2)0.044 (2)0.0062 (19)−0.0159 (18)−0.0114 (18)
C240.053 (2)0.042 (2)0.0401 (19)−0.0008 (17)−0.0012 (16)−0.0061 (16)
N10.0388 (15)0.0395 (15)0.0423 (16)−0.0044 (13)0.0074 (12)−0.0037 (13)
N20.0432 (16)0.0361 (14)0.0295 (12)0.0032 (12)0.0015 (11)−0.0020 (11)
O10.0520 (14)0.0380 (12)0.0322 (11)0.0053 (10)−0.0061 (10)−0.0038 (9)
O20.0518 (14)0.0400 (13)0.0436 (13)0.0029 (12)−0.0086 (11)−0.0076 (11)
O30.0403 (12)0.0297 (12)0.0456 (12)0.0018 (10)−0.0019 (10)0.0082 (10)
O40.0539 (15)0.0333 (14)0.114 (2)−0.0040 (13)0.0030 (16)0.0071 (15)
O50.0418 (12)0.0328 (12)0.0436 (13)0.0019 (10)0.0014 (11)−0.0006 (10)
O60.0465 (15)0.0415 (14)0.0519 (15)0.0074 (11)−0.0036 (12)−0.0072 (12)
Geometric parameters (Å, °) top
Ni1—O3i2.098 (2)C13—C141.533 (4)
Ni1—O12.103 (2)C14—O21.255 (4)
Ni1—O62.142 (2)C14—O11.276 (3)
Ni1—O52.149 (2)C15—N11.351 (4)
Ni1—N12.166 (3)C15—C161.383 (5)
Ni1—N22.168 (2)C15—H150.930
C1—O41.233 (4)C16—C171.391 (6)
C1—O31.247 (4)C16—H160.930
C1—C21.543 (5)C17—C181.379 (6)
C2—C31.388 (5)C17—H170.930
C2—C71.412 (5)C18—C191.406 (5)
C3—C41.380 (6)C18—H180.930
C3—H30.930C19—N11.361 (4)
C4—C51.385 (6)C19—C201.493 (5)
C4—H40.930C20—N21.352 (4)
C5—C61.391 (5)C20—C211.419 (4)
C5—H50.930C21—C221.385 (6)
C6—C71.427 (4)C21—H210.930
C6—H60.930C22—C231.374 (5)
C7—C81.514 (4)C22—H220.930
C8—C131.374 (5)C23—C241.409 (5)
C8—C91.414 (4)C23—H230.930
C9—C101.373 (5)C24—N21.357 (4)
C9—H90.930C24—H240.930
C10—C111.358 (6)O3—Ni1ii2.098 (2)
C10—H100.930O5—H1W0.86 (2)
C11—C121.402 (5)O5—H2W0.85 (2)
C11—H110.930O6—H3W0.81 (2)
C12—C131.385 (4)O6—H4W0.82 (2)
C12—H120.930
O3i—Ni1—O195.44 (8)C8—C13—C12118.5 (3)
O3i—Ni1—O693.63 (9)C8—C13—C14121.3 (3)
O1—Ni1—O692.16 (9)C12—C13—C14120.1 (3)
O3i—Ni1—O589.65 (8)O2—C14—O1124.7 (3)
O1—Ni1—O581.77 (8)O2—C14—C13117.1 (3)
O6—Ni1—O5173.36 (9)O1—C14—C13118.1 (3)
O3i—Ni1—N1169.97 (9)N1—C15—C16121.5 (4)
O1—Ni1—N193.86 (9)N1—C15—H15119.2
O6—Ni1—N189.75 (10)C16—C15—H15119.2
O5—Ni1—N187.97 (9)C15—C16—C17119.3 (4)
O3i—Ni1—N294.20 (9)C15—C16—H16120.3
O1—Ni1—N2165.48 (9)C17—C16—H16120.4
O6—Ni1—N298.04 (9)C18—C17—C16119.8 (4)
O5—Ni1—N287.46 (9)C18—C17—H17120.1
N1—Ni1—N275.96 (10)C16—C17—H17120.1
O4—C1—O3124.2 (3)C17—C18—C19118.7 (4)
O4—C1—C2118.9 (3)C17—C18—H18120.7
O3—C1—C2116.9 (3)C19—C18—H18120.7
C3—C2—C7117.8 (3)N1—C19—C18121.1 (3)
C3—C2—C1117.3 (3)N1—C19—C20115.7 (3)
C7—C2—C1124.9 (3)C18—C19—C20123.2 (3)
C4—C3—C2122.3 (4)N2—C20—C21121.7 (3)
C4—C3—H3118.8N2—C20—C19115.4 (3)
C2—C3—H3118.8C21—C20—C19122.9 (3)
C5—C4—C3120.5 (3)C22—C21—C20119.2 (4)
C5—C4—H4119.7C22—C21—H21120.4
C3—C4—H4119.7C20—C21—H21120.4
C4—C5—C6119.4 (3)C23—C22—C21119.5 (3)
C4—C5—H5120.3C23—C22—H22120.3
C6—C5—H5120.3C21—C22—H22120.3
C5—C6—C7120.0 (4)C22—C23—C24119.0 (3)
C5—C6—H6120.0C22—C23—H23120.5
C7—C6—H6120.0C24—C23—H23120.5
C2—C7—C6119.8 (3)N2—C24—C23122.5 (3)
C2—C7—C8122.7 (3)N2—C24—H24118.7
C6—C7—C8116.9 (3)C23—C24—H24118.7
C13—C8—C9116.8 (3)C15—N1—C19119.5 (3)
C13—C8—C7124.4 (3)C15—N1—Ni1124.1 (2)
C9—C8—C7118.8 (3)C19—N1—Ni1115.6 (2)
C10—C9—C8124.3 (3)C20—N2—C24118.1 (3)
C10—C9—H9117.9C20—N2—Ni1116.4 (2)
C8—C9—H9117.8C24—N2—Ni1125.4 (2)
C11—C10—C9118.5 (3)C14—O1—Ni1132.81 (19)
C11—C10—H10120.7C1—O3—Ni1ii129.1 (2)
C9—C10—H10120.8Ni1—O5—H1W99 (2)
C10—C11—C12118.1 (3)Ni1—O5—H2W117 (2)
C10—C11—H11121.0H1W—O5—H2W104 (2)
C12—C11—H11120.9Ni1—O6—H3W102 (3)
C13—C12—C11123.6 (3)Ni1—O6—H4W95 (3)
C13—C12—H12118.2H3W—O6—H4W112 (3)
C11—C12—H12118.2
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x+1/2, −y+3/2, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H1W···Cg10.86 (2)2.913.741 (3)163
O5—H2W···O2i0.85 (2)1.90 (2)2.740 (3)169 (3)
O6—H3W···O4i0.81 (2)1.91 (2)2.676 (4)158 (4)
O6—H4W···O20.82 (2)1.98 (2)2.790 (3)167 (4)
Symmetry codes: (i) x−1/2, −y+3/2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H1W···Cg10.86 (2)2.913.741 (3)163
O5—H2W···O2i0.85 (2)1.90 (2)2.740 (3)169 (3)
O6—H3W···O4i0.81 (2)1.91 (2)2.676 (4)158 (4)
O6—H4W···O20.82 (2)1.98 (2)2.790 (3)167 (4)
Symmetry codes: (i) x−1/2, −y+3/2, −z+2.
Acknowledgements top

The authors acknowledge financial support from Maoming University.

references
References top

Bruker (2001). SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Rueff, J.-M., Pillet, S., Bonaventure, G., Souhassou, M. & Rabu, P. (2003). Eur. J. Inorg. Chem. pp. 4173–4178.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, R.-H., Gong, Y.-Q., Han, L., Yuan, D.-Q., Lou, B.-Y., Wu, B.-L. & Hong, M.-C. (2006). J. Mol. Struct. 784, 1–6.

Xu, X.-X., Lu, Y., Wang, E.-B., Ma, Y. & Bai, X.-L. (2006). Cryst. Growth Des. 6, 2029–2035.