metal-organic compounds
catena-Poly[[diaqua(1,10-phenanthroline-κ2N,N′)nickel(II)]-μ-1H-benzimidazole-5,6-dicarboxylato-κ2N3:O6]
aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: songwd60@126.com
In the title complex, [Ni(C9H4N2O4)(C12H8N2)(H2O)2]n, the NiII atom is hexacoordinated by one N and one O atom from two different 1H-benzimidazole-5,6-dicarboxylate ligands, two N atoms from one 1,10-phenanthroline ligand and two water molecules. The flexible 1H-benzimidazole-5,6-dicarboxylate ligands link the NiII centres, forming an infinite zigzag chain parallel to [001]. The crystal packing is governed by intermolecular hydrogen-bonding interactions of the O—H⋯O, N—H⋯O and C—H⋯O types.
Related literature
For background to 1H-benzoimidazole-5,6-dicarboxylate complexes, see: Lo et al. (2007); Yao et al. (2008); Gao et al. (2008). For background to 1,10-phenanthroline complexes, see: Chesnut et al. (1999).
Experimental
Crystal data
|
Refinement
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809019680/im2119sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809019680/im2119Isup2.hkl
A mixture of nickel chloride (1 mmol), 1H-benzimidazole-5,6-dicarboxylic acid (1 mmol), 1,10-phenanthroline (1 mmol), NaOH (1.5 mmol) and H2O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h-1. The crystals obtained were washed with water and dryed in air.
Carbon and nitrogen bound H atoms were placed at calculated positions and were treated as riding on the parent C or N atoms with C—H = 0.93 Å, N—H = 0.86 Å, and with Uiso(H) = 1.2 Ueq(C, N). The water H-atoms were located in a difference map, and were refined with a distance restraint of O—H = 0.84 Å; their Uiso values were refined.
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids. [Symmetry codes: (i) x, 1/2 - y, 1/2 + z. | |
Fig. 2. A view of the infinite chain of title compound. | |
Fig. 3. A view of the two-dimensional layer constructed by O—H···O and C—H···O hydrogen bonding interactions. |
[Ni(C9H4N2O4)(C12H8N2)(H2O)2] | F(000) = 984 |
Mr = 479.09 | Dx = 1.572 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3600 reflections |
a = 10.021 (2) Å | θ = 1.4–28° |
b = 16.980 (3) Å | µ = 1.01 mm−1 |
c = 15.327 (5) Å | T = 293 K |
β = 129.09 (2)° | Block, blue |
V = 2024.3 (9) Å3 | 0.31 × 0.26 × 0.22 mm |
Z = 4 |
Rigaku/MSC Mercury CCD diffractometer | 3639 independent reflections |
Radiation source: fine-focus sealed tube | 3195 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 25.2°, θmin = 3.2° |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | h = −11→12 |
Tmin = 0.746, Tmax = 0.809 | k = −20→20 |
15765 measured reflections | l = −18→18 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.2141P] where P = (Fo2 + 2Fc2)/3 |
3639 reflections | (Δ/σ)max = 0.001 |
289 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
[Ni(C9H4N2O4)(C12H8N2)(H2O)2] | V = 2024.3 (9) Å3 |
Mr = 479.09 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.021 (2) Å | µ = 1.01 mm−1 |
b = 16.980 (3) Å | T = 293 K |
c = 15.327 (5) Å | 0.31 × 0.26 × 0.22 mm |
β = 129.09 (2)° |
Rigaku/MSC Mercury CCD diffractometer | 3639 independent reflections |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | 3195 reflections with I > 2σ(I) |
Tmin = 0.746, Tmax = 0.809 | Rint = 0.039 |
15765 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.37 e Å−3 |
3639 reflections | Δρmin = −0.25 e Å−3 |
289 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 | 0.55530 (3) | 0.434786 (13) | 0.82246 (2) | 0.02591 (11) | |
O1 | 0.38387 (19) | 0.10540 (8) | 0.49825 (13) | 0.0398 (4) | |
O1W | 0.76448 (17) | 0.50597 (8) | 0.94690 (12) | 0.0318 (3) | |
H1W | 0.7283 | 0.5441 | 0.9617 | 0.048* | |
H2W | 0.8137 | 0.4736 | 1.0003 | 0.048* | |
O2 | 0.27333 (18) | 0.22040 (9) | 0.41361 (14) | 0.0456 (4) | |
O2W | 0.39504 (19) | 0.49621 (9) | 0.84828 (13) | 0.0395 (4) | |
H3W | 0.4521 | 0.5341 | 0.8920 | 0.059* | |
H4W | 0.3796 | 0.4618 | 0.8805 | 0.059* | |
O3 | 0.59904 (17) | 0.14247 (8) | 0.43858 (11) | 0.0314 (3) | |
O4 | 0.86749 (19) | 0.10944 (10) | 0.58603 (13) | 0.0479 (4) | |
N1 | 0.7201 (2) | 0.37301 (10) | 0.80627 (14) | 0.0296 (4) | |
N2 | 0.9708 (2) | 0.34131 (11) | 0.84962 (15) | 0.0357 (4) | |
H2 | 1.0793 | 0.3421 | 0.8837 | 0.043* | |
N3 | 0.3234 (2) | 0.38391 (10) | 0.68890 (14) | 0.0334 (4) | |
N5 | 0.4878 (3) | 0.51071 (11) | 0.69453 (16) | 0.0407 (4) | |
C1 | 0.5577 (2) | 0.22029 (11) | 0.58394 (16) | 0.0259 (4) | |
C2 | 0.7187 (2) | 0.20098 (11) | 0.61273 (16) | 0.0277 (4) | |
C3 | 0.8679 (2) | 0.23640 (12) | 0.70388 (17) | 0.0300 (4) | |
H3 | 0.9750 | 0.2227 | 0.7257 | 0.036* | |
C4 | 0.8508 (2) | 0.29313 (12) | 0.76130 (16) | 0.0288 (4) | |
C5 | 0.6930 (2) | 0.31336 (11) | 0.73392 (16) | 0.0261 (4) | |
C6 | 0.5439 (2) | 0.27566 (11) | 0.64394 (17) | 0.0273 (4) | |
H6 | 0.4378 | 0.2875 | 0.6248 | 0.033* | |
C7 | 0.8876 (3) | 0.38666 (13) | 0.87258 (18) | 0.0355 (5) | |
H7 | 0.9419 | 0.4241 | 0.9296 | 0.043* | |
C8 | 0.3932 (2) | 0.17945 (12) | 0.48969 (17) | 0.0296 (4) | |
C9 | 0.7307 (2) | 0.14601 (11) | 0.54114 (17) | 0.0297 (4) | |
C10 | 0.2431 (3) | 0.32210 (15) | 0.6884 (2) | 0.0456 (6) | |
H10 | 0.2925 | 0.2953 | 0.7554 | 0.055* | |
C11 | 0.0856 (3) | 0.29550 (19) | 0.5899 (3) | 0.0632 (8) | |
H11 | 0.0322 | 0.2514 | 0.5915 | 0.076* | |
C12 | 0.0117 (3) | 0.33512 (19) | 0.4919 (2) | 0.0622 (8) | |
H12 | −0.0927 | 0.3178 | 0.4263 | 0.075* | |
C13 | 0.0909 (3) | 0.40118 (17) | 0.4888 (2) | 0.0523 (7) | |
C14 | 0.0237 (4) | 0.4466 (2) | 0.3894 (2) | 0.0712 (9) | |
H14 | −0.0821 | 0.4332 | 0.3217 | 0.085* | |
C15 | 0.1116 (5) | 0.5081 (2) | 0.3928 (2) | 0.0775 (10) | |
H15 | 0.0667 | 0.5352 | 0.3268 | 0.093* | |
C16 | 0.2709 (4) | 0.53257 (17) | 0.4943 (2) | 0.0600 (7) | |
C17 | 0.3695 (5) | 0.59590 (19) | 0.5046 (3) | 0.0785 (10) | |
H17 | 0.3296 | 0.6257 | 0.4415 | 0.094* | |
C18 | 0.5209 (5) | 0.61432 (19) | 0.6043 (3) | 0.0812 (10) | |
H18 | 0.5865 | 0.6558 | 0.6099 | 0.097* | |
C19 | 0.5781 (4) | 0.57061 (14) | 0.6991 (3) | 0.0577 (7) | |
H19 | 0.6827 | 0.5836 | 0.7678 | 0.069* | |
C20 | 0.3383 (3) | 0.49073 (13) | 0.59409 (19) | 0.0406 (5) | |
C21 | 0.2485 (3) | 0.42380 (14) | 0.59078 (19) | 0.0391 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02516 (17) | 0.02713 (17) | 0.02261 (17) | 0.00032 (8) | 0.01370 (14) | 0.00058 (9) |
O1 | 0.0485 (9) | 0.0309 (8) | 0.0463 (9) | −0.0124 (6) | 0.0330 (8) | −0.0050 (6) |
O1W | 0.0337 (8) | 0.0273 (7) | 0.0319 (8) | −0.0008 (5) | 0.0196 (7) | −0.0031 (6) |
O2 | 0.0250 (8) | 0.0409 (9) | 0.0475 (10) | 0.0004 (6) | 0.0117 (8) | −0.0029 (7) |
O2W | 0.0397 (8) | 0.0405 (8) | 0.0361 (9) | 0.0052 (6) | 0.0228 (8) | −0.0012 (6) |
O3 | 0.0311 (7) | 0.0347 (7) | 0.0257 (7) | 0.0014 (5) | 0.0165 (7) | −0.0032 (6) |
O4 | 0.0298 (8) | 0.0577 (10) | 0.0384 (9) | 0.0097 (7) | 0.0130 (7) | −0.0155 (8) |
N1 | 0.0280 (9) | 0.0324 (9) | 0.0272 (9) | −0.0026 (6) | 0.0168 (8) | −0.0065 (7) |
N2 | 0.0222 (8) | 0.0463 (10) | 0.0297 (9) | −0.0029 (7) | 0.0121 (8) | −0.0118 (8) |
N3 | 0.0301 (9) | 0.0417 (10) | 0.0281 (9) | 0.0000 (7) | 0.0181 (8) | −0.0045 (7) |
N5 | 0.0483 (11) | 0.0373 (10) | 0.0342 (10) | 0.0045 (8) | 0.0250 (10) | 0.0062 (8) |
C1 | 0.0247 (10) | 0.0249 (9) | 0.0250 (10) | −0.0008 (7) | 0.0141 (9) | 0.0011 (7) |
C2 | 0.0266 (10) | 0.0275 (10) | 0.0249 (10) | 0.0023 (7) | 0.0142 (9) | 0.0004 (8) |
C3 | 0.0238 (9) | 0.0356 (11) | 0.0280 (10) | 0.0020 (8) | 0.0150 (9) | −0.0013 (8) |
C4 | 0.0247 (9) | 0.0324 (10) | 0.0234 (10) | −0.0004 (7) | 0.0123 (9) | −0.0004 (8) |
C5 | 0.0273 (9) | 0.0259 (9) | 0.0253 (10) | 0.0003 (7) | 0.0167 (9) | 0.0006 (8) |
C6 | 0.0227 (9) | 0.0301 (10) | 0.0306 (11) | −0.0013 (7) | 0.0175 (9) | −0.0022 (8) |
C7 | 0.0290 (11) | 0.0405 (12) | 0.0309 (11) | −0.0045 (8) | 0.0159 (10) | −0.0123 (9) |
C8 | 0.0283 (10) | 0.0314 (11) | 0.0331 (11) | −0.0057 (8) | 0.0212 (9) | −0.0058 (8) |
C9 | 0.0251 (10) | 0.0316 (10) | 0.0296 (11) | −0.0026 (8) | 0.0160 (9) | −0.0027 (8) |
C10 | 0.0447 (13) | 0.0568 (15) | 0.0428 (13) | −0.0148 (11) | 0.0311 (12) | −0.0131 (11) |
C11 | 0.0558 (16) | 0.084 (2) | 0.0632 (19) | −0.0333 (15) | 0.0437 (16) | −0.0301 (16) |
C12 | 0.0387 (14) | 0.091 (2) | 0.0433 (16) | −0.0135 (13) | 0.0195 (13) | −0.0268 (15) |
C13 | 0.0389 (13) | 0.0677 (17) | 0.0340 (13) | 0.0058 (12) | 0.0152 (12) | −0.0118 (12) |
C14 | 0.0542 (18) | 0.091 (2) | 0.0265 (14) | 0.0131 (15) | 0.0055 (14) | −0.0051 (13) |
C15 | 0.085 (2) | 0.079 (2) | 0.0324 (15) | 0.0178 (18) | 0.0202 (16) | 0.0141 (14) |
C16 | 0.0776 (19) | 0.0562 (16) | 0.0387 (14) | 0.0174 (14) | 0.0330 (15) | 0.0119 (12) |
C17 | 0.110 (3) | 0.0605 (19) | 0.056 (2) | 0.0062 (18) | 0.048 (2) | 0.0265 (15) |
C18 | 0.112 (3) | 0.0601 (19) | 0.069 (2) | −0.0128 (18) | 0.056 (2) | 0.0185 (16) |
C19 | 0.0712 (19) | 0.0452 (15) | 0.0536 (17) | −0.0087 (12) | 0.0378 (16) | 0.0068 (11) |
C20 | 0.0473 (13) | 0.0392 (12) | 0.0311 (12) | 0.0119 (9) | 0.0227 (11) | 0.0060 (9) |
C21 | 0.0332 (12) | 0.0501 (13) | 0.0249 (11) | 0.0109 (9) | 0.0140 (10) | −0.0035 (9) |
Ni1—O3i | 2.0241 (14) | C2—C9 | 1.502 (3) |
Ni1—N5 | 2.0715 (19) | C3—C4 | 1.386 (3) |
Ni1—N3 | 2.0828 (18) | C3—H3 | 0.9300 |
Ni1—N1 | 2.0994 (16) | C4—C5 | 1.399 (3) |
Ni1—O1W | 2.1098 (15) | C5—C6 | 1.395 (3) |
Ni1—O2W | 2.1507 (15) | C6—H6 | 0.9300 |
O1—C8 | 1.274 (2) | C7—H7 | 0.9300 |
O1W—H1W | 0.8402 | C10—C11 | 1.404 (3) |
O1W—H2W | 0.8401 | C10—H10 | 0.9300 |
O2—C8 | 1.233 (2) | C11—C12 | 1.362 (4) |
O2W—H3W | 0.8400 | C11—H11 | 0.9300 |
O2W—H4W | 0.8400 | C12—C13 | 1.392 (4) |
O3—C9 | 1.265 (2) | C12—H12 | 0.9300 |
O3—Ni1ii | 2.0241 (14) | C13—C21 | 1.404 (3) |
O4—C9 | 1.244 (2) | C13—C14 | 1.441 (4) |
N1—C7 | 1.323 (3) | C14—C15 | 1.345 (5) |
N1—C5 | 1.396 (3) | C14—H14 | 0.9300 |
N2—C7 | 1.335 (3) | C15—C16 | 1.418 (4) |
N2—C4 | 1.376 (3) | C15—H15 | 0.9300 |
N2—H2 | 0.8600 | C16—C17 | 1.400 (5) |
N3—C10 | 1.319 (3) | C16—C20 | 1.413 (3) |
N3—C21 | 1.364 (3) | C17—C18 | 1.346 (5) |
N5—C19 | 1.334 (3) | C17—H17 | 0.9300 |
N5—C20 | 1.350 (3) | C18—C19 | 1.393 (4) |
C1—C6 | 1.381 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.417 (3) | C19—H19 | 0.9300 |
C1—C8 | 1.510 (3) | C20—C21 | 1.431 (3) |
C2—C3 | 1.384 (3) | ||
O3i—Ni1—N5 | 174.88 (7) | C1—C6—C5 | 118.45 (17) |
O3i—Ni1—N3 | 94.83 (7) | C1—C6—H6 | 120.8 |
N5—Ni1—N3 | 80.31 (8) | C5—C6—H6 | 120.8 |
O3i—Ni1—N1 | 91.71 (6) | N1—C7—N2 | 113.37 (18) |
N5—Ni1—N1 | 90.62 (8) | N1—C7—H7 | 123.3 |
N3—Ni1—N1 | 98.62 (7) | N2—C7—H7 | 123.3 |
O3i—Ni1—O1W | 92.03 (6) | O2—C8—O1 | 124.26 (18) |
N5—Ni1—O1W | 92.56 (7) | O2—C8—C1 | 118.08 (18) |
N3—Ni1—O1W | 169.42 (6) | O1—C8—C1 | 117.48 (17) |
N1—Ni1—O1W | 89.19 (6) | O4—C9—O3 | 125.86 (19) |
O3i—Ni1—O2W | 85.71 (6) | O4—C9—C2 | 118.28 (17) |
N5—Ni1—O2W | 92.07 (7) | O3—C9—C2 | 115.85 (16) |
N3—Ni1—O2W | 83.24 (7) | N3—C10—C11 | 122.1 (2) |
N1—Ni1—O2W | 176.95 (6) | N3—C10—H10 | 119.0 |
O1W—Ni1—O2W | 89.27 (6) | C11—C10—H10 | 119.0 |
Ni1—O1W—H1W | 109.5 | C12—C11—C10 | 119.2 (3) |
Ni1—O1W—H2W | 98.3 | C12—C11—H11 | 120.4 |
H1W—O1W—H2W | 109.2 | C10—C11—H11 | 120.4 |
Ni1—O2W—H3W | 107.8 | C11—C12—C13 | 120.7 (2) |
Ni1—O2W—H4W | 102.0 | C11—C12—H12 | 119.6 |
H3W—O2W—H4W | 110.4 | C13—C12—H12 | 119.6 |
C9—O3—Ni1ii | 126.97 (12) | C12—C13—C21 | 116.6 (2) |
C7—N1—C5 | 104.75 (16) | C12—C13—C14 | 124.8 (3) |
C7—N1—Ni1 | 122.19 (14) | C21—C13—C14 | 118.6 (3) |
C5—N1—Ni1 | 133.06 (13) | C15—C14—C13 | 121.1 (3) |
C7—N2—C4 | 107.40 (17) | C15—C14—H14 | 119.5 |
C7—N2—H2 | 126.3 | C13—C14—H14 | 119.5 |
C4—N2—H2 | 126.3 | C14—C15—C16 | 121.8 (3) |
C10—N3—C21 | 118.60 (19) | C14—C15—H15 | 119.1 |
C10—N3—Ni1 | 129.35 (15) | C16—C15—H15 | 119.1 |
C21—N3—Ni1 | 112.04 (15) | C17—C16—C15 | 125.1 (3) |
C19—N5—C20 | 118.7 (2) | C17—C16—C20 | 116.3 (3) |
C19—N5—Ni1 | 128.25 (18) | C15—C16—C20 | 118.6 (3) |
C20—N5—Ni1 | 112.85 (15) | C18—C17—C16 | 121.1 (3) |
C6—C1—C2 | 121.47 (17) | C18—C17—H17 | 119.5 |
C6—C1—C8 | 116.26 (16) | C16—C17—H17 | 119.5 |
C2—C1—C8 | 122.22 (17) | C17—C18—C19 | 119.2 (3) |
C3—C2—C1 | 120.47 (18) | C17—C18—H18 | 120.4 |
C3—C2—C9 | 118.32 (17) | C19—C18—H18 | 120.4 |
C1—C2—C9 | 121.09 (16) | N5—C19—C18 | 122.2 (3) |
C4—C3—C2 | 117.13 (18) | N5—C19—H19 | 118.9 |
C4—C3—H3 | 121.4 | C18—C19—H19 | 118.9 |
C2—C3—H3 | 121.4 | N5—C20—C16 | 122.5 (2) |
N2—C4—C3 | 131.06 (18) | N5—C20—C21 | 117.47 (19) |
N2—C4—C5 | 105.66 (17) | C16—C20—C21 | 120.0 (2) |
C3—C4—C5 | 123.27 (18) | N3—C21—C13 | 122.9 (2) |
N1—C5—C6 | 131.99 (17) | N3—C21—C20 | 117.3 (2) |
N1—C5—C4 | 108.82 (16) | C13—C21—C20 | 119.8 (2) |
C6—C5—C4 | 119.16 (18) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1iii | 0.84 | 1.90 | 2.710 (2) | 163 |
O1W—H2W···O4i | 0.84 | 1.76 | 2.584 (2) | 165 |
O2W—H3W···O1iii | 0.84 | 1.87 | 2.703 (2) | 169 |
O2W—H4W···O1i | 0.84 | 2.11 | 2.932 (2) | 165 |
N2—H2···O2iv | 0.86 | 2.00 | 2.739 (2) | 144 |
N2—H2···O1iv | 0.86 | 2.54 | 3.355 (2) | 159 |
C10—H10···O2i | 0.93 | 2.56 | 3.346 (8) | 143 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C9H4N2O4)(C12H8N2)(H2O)2] |
Mr | 479.09 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.021 (2), 16.980 (3), 15.327 (5) |
β (°) | 129.09 (2) |
V (Å3) | 2024.3 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.01 |
Crystal size (mm) | 0.31 × 0.26 × 0.22 |
Data collection | |
Diffractometer | Rigaku/MSC Mercury CCD diffractometer |
Absorption correction | Multi-scan (REQAB; Jacobson, 1998) |
Tmin, Tmax | 0.746, 0.809 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15765, 3639, 3195 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.091, 1.09 |
No. of reflections | 3639 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.25 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1i | 0.84 | 1.90 | 2.710 (2) | 162.8 |
O1W—H2W···O4ii | 0.84 | 1.76 | 2.584 (2) | 164.6 |
O2W—H3W···O1i | 0.84 | 1.87 | 2.703 (2) | 168.9 |
O2W—H4W···O1ii | 0.84 | 2.11 | 2.932 (2) | 165.0 |
N2—H2···O2iii | 0.86 | 2.00 | 2.739 (2) | 143.8 |
N2—H2···O1iii | 0.86 | 2.54 | 3.355 (2) | 159.2 |
C10—H10···O2ii | 0.93 | 2.56 | 3.346 (8) | 143 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z+1/2. |
Acknowledgements
The authors acknowledge Guang Dong Ocean University for support of this work.
References
Chesnut, D. J., Haushalter, R. C. & Zubieta, J. (1999). Inorg. Chim. Acta, 292, 41–51. Web of Science CSD CrossRef CAS Google Scholar
Gao, Q., Gao, W.-H., Zhang, C.-Y. & Xie, Y.-B. (2008). Acta Cryst. E64, m928. Web of Science CrossRef IUCr Journals Google Scholar
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Lo, Y.-L., Wang, W.-C., Lee, G.-A. & Liu, Y.-H. (2007). Acta Cryst. E63, m2657–m2658. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yao, Y. L., Che, Y. X. & Zheng, J. M. (2008). Cryst. Growth Des. 8, 2299–2306. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In the structural investigation of 1H-benzimidazole-5,6-dicarboxylate complexes, it has been found that 1H-benzimidazole-5,6-dicarboxylic acid can function as a multidentate ligand (Lo et al., 2007; Yao et al., 2008; Gao et al., 2008), with versatile binding and coordination modes. 1,10-Phenanthroline is also a good example for a bridging ligand that can link metal centres into extended networks, and a number of one-, two- and three- dimensional metal-1,10-phenanthroline frameworks have been generated (Chesnut et al., 1999). The reaction of 1H-benzimidazole-5,6-dicarboxylic acid with nickel chloride in an alkaline aqueous solution yielded a new NiII coordination polymer, whose crystal structure is reported here.
As illustrated in Figure 1, the NiII atom exhibits a slightly distorted octahedral coordination sphere, defined by one N and one O atom from two different 1H-benzimidazole-5,6-dicarboxylate ligands, two N atoms from one 1,10-phenanthroline ligand and two water molecules. The metal atoms are linked by bidentate 1H-benzimidazole-5,6-dicarboxylate groups into a linear chain (Fig. 2). Inter/intramolecular O—H···O and C—H···O hydrogen bonds between the carboxylate O atoms of 1H-benzimidazole-5,6-dicarboxylate and the coordinated water molecule lead to a two-dimensional layer (Fig. 3). The layers are further self-assembled into a three-dimensional supramolecular network by intermolecular N—H···O hydrogen bonds between the imidazole units and carboxylate groups (Table 1).