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metal-organic compounds
In the title compound, [Ni2(C10H2O8)(C10H8N2)2(H2O)6].2H2O, the benzenetetracarboxylate anion, which lies on a center of symmetry, is monodentate to two bipyridine-chelated water-coordinated Ni atoms. The geometry of the Ni atom is that of an octahedron. The coordinated and uncoordinated water molecules are linked by hydrogen bonds into a network structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000807/ng6008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000807/ng6008Isup2.hkl |
CCDC reference: 234831
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.029
- wR factor = 0.078
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O1W = 5.66 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8 PLAT731_ALERT_1_C Bond Calc 0.84(2), Rep 0.844(9) ...... 2.22 su-Rat O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(2), Rep 0.848(7) ...... 2.86 su-Rat O2W -H2W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(2), Rep 0.844(9) ...... 2.22 su-Rat O3W -H3W2 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
µ-Benzene-1,2,4,5-tetracarboxylato-bis[triaqua(2,2'-bipyridine)nickel(II)]
dihydrate top
Crystal data top
[Ni2(C10H2O8)(C10H8N2)2(H2O)6]·2H2O | Z = 1 |
Mr = 824.03 | F(000) = 426 |
Triclinic, P1 | Dx = 1.617 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5839 (4) Å | Cell parameters from 4405 reflections |
b = 9.7257 (6) Å | θ = 2.5–25.2° |
c = 11.9698 (7) Å | µ = 1.19 mm−1 |
α = 76.927 (1)° | T = 298 K |
β = 87.388 (1)° | Prism, green |
γ = 79.807 (1)° | 0.35 × 0.32 × 0.17 mm |
V = 846.41 (8) Å3 |
Data collection top
Bruker APEX area-detector diffractometer | 3036 independent reflections |
Radiation source: fine-focus sealed tube | 2903 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
φ and ω scans | θmax = 25.2°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.680, Tmax = 0.823 | k = −11→11 |
6271 measured reflections | l = −14→14 |
Refinement top
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0459P)2 + 0.4734P] where P = (Fo2 + 2Fc2)/3 |
3036 reflections | (Δ/σ)max < 0.001 |
259 parameters | Δρmax = 0.27 e Å−3 |
12 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.76992 (3) | 0.95545 (2) | 0.726032 (19) | 0.02501 (10) | |
O1 | 0.82261 (18) | 0.77865 (15) | 0.65552 (12) | 0.0306 (3) | |
O2 | 1.1004 (2) | 0.68798 (17) | 0.71627 (14) | 0.0418 (4) | |
O3 | 0.55015 (19) | 0.72201 (16) | 0.48432 (14) | 0.0398 (4) | |
O4 | 0.74530 (19) | 0.86276 (15) | 0.40825 (13) | 0.0360 (3) | |
O1w | 0.7452 (2) | 1.07114 (17) | 0.55743 (13) | 0.0371 (3) | |
H1w1 | 0.750 (3) | 1.0091 (19) | 0.5177 (19) | 0.044* | |
H1w2 | 0.650 (2) | 1.1327 (19) | 0.542 (2) | 0.044* | |
O2w | 0.50095 (19) | 0.94274 (17) | 0.73220 (13) | 0.0351 (3) | |
H2w1 | 0.487 (3) | 0.8614 (18) | 0.728 (2) | 0.042* | |
H2w2 | 0.433 (3) | 1.0063 (18) | 0.6851 (17) | 0.042* | |
O3w | 1.04139 (19) | 0.96637 (16) | 0.72852 (13) | 0.0346 (3) | |
H3w1 | 1.092 (3) | 0.8821 (11) | 0.725 (2) | 0.041* | |
H3w2 | 1.088 (3) | 1.0265 (17) | 0.6791 (17) | 0.041* | |
O4w | 1.4545 (2) | 0.6821 (2) | 0.71499 (17) | 0.0531 (5) | |
H4w1 | 1.3435 (15) | 0.677 (3) | 0.714 (2) | 0.064* | |
H4w2 | 1.499 (3) | 0.676 (3) | 0.6495 (14) | 0.064* | |
N1 | 0.7863 (2) | 0.84966 (18) | 0.89611 (14) | 0.0294 (4) | |
N2 | 0.7255 (2) | 1.12748 (19) | 0.80412 (16) | 0.0357 (4) | |
C1 | 0.8152 (3) | 0.7082 (2) | 0.9368 (2) | 0.0420 (5) | |
H1 | 0.8287 | 0.6486 | 0.8852 | 0.050* | |
C2 | 0.8256 (4) | 0.6472 (3) | 1.0523 (2) | 0.0601 (7) | |
H2 | 0.8448 | 0.5481 | 1.0784 | 0.072* | |
C3 | 0.8069 (5) | 0.7354 (4) | 1.1277 (2) | 0.0767 (10) | |
H3 | 0.8167 | 0.6969 | 1.2061 | 0.092* | |
C4 | 0.7737 (5) | 0.8806 (3) | 1.0872 (2) | 0.0646 (8) | |
H4 | 0.7579 | 0.9416 | 1.1380 | 0.078* | |
C5 | 0.7640 (3) | 0.9359 (2) | 0.97050 (18) | 0.0351 (5) | |
C6 | 0.7300 (3) | 1.0912 (2) | 0.9193 (2) | 0.0385 (5) | |
C7 | 0.7052 (4) | 1.1939 (3) | 0.9844 (3) | 0.0645 (8) | |
H7 | 0.7066 | 1.1670 | 1.0640 | 0.077* | |
C8 | 0.6786 (5) | 1.3356 (4) | 0.9301 (4) | 0.0828 (11) | |
H8 | 0.6606 | 1.4059 | 0.9727 | 0.099* | |
C9 | 0.6783 (5) | 1.3737 (3) | 0.8129 (4) | 0.0794 (11) | |
H9 | 0.6628 | 1.4696 | 0.7749 | 0.095* | |
C10 | 0.7018 (4) | 1.2667 (3) | 0.7519 (3) | 0.0565 (7) | |
H10 | 0.7010 | 1.2921 | 0.6722 | 0.068* | |
C11 | 0.9704 (3) | 0.6966 (2) | 0.65284 (16) | 0.0276 (4) | |
C12 | 0.9859 (2) | 0.5992 (2) | 0.56987 (16) | 0.0250 (4) | |
C13 | 0.8569 (2) | 0.6166 (2) | 0.48559 (16) | 0.0245 (4) | |
C14 | 0.7051 (3) | 0.7444 (2) | 0.45946 (16) | 0.0276 (4) | |
C15 | 0.8717 (3) | 0.5159 (2) | 0.41881 (16) | 0.0263 (4) | |
H15 | 0.7838 | 0.5252 | 0.3646 | 0.032* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02586 (16) | 0.02447 (15) | 0.02405 (15) | 0.00147 (10) | −0.00248 (10) | −0.00809 (10) |
O1 | 0.0269 (7) | 0.0326 (7) | 0.0342 (8) | 0.0049 (6) | −0.0037 (6) | −0.0180 (6) |
O2 | 0.0324 (8) | 0.0483 (9) | 0.0479 (9) | 0.0096 (7) | −0.0145 (7) | −0.0273 (8) |
O3 | 0.0242 (8) | 0.0334 (8) | 0.0589 (10) | 0.0026 (6) | −0.0043 (7) | −0.0096 (7) |
O4 | 0.0342 (8) | 0.0261 (7) | 0.0415 (8) | 0.0028 (6) | −0.0024 (6) | −0.0004 (6) |
O1w | 0.0375 (8) | 0.0369 (8) | 0.0309 (8) | 0.0067 (7) | −0.0040 (6) | −0.0049 (6) |
O2w | 0.0275 (8) | 0.0364 (8) | 0.0381 (8) | 0.0024 (6) | −0.0040 (6) | −0.0070 (7) |
O3w | 0.0304 (8) | 0.0313 (8) | 0.0429 (9) | −0.0049 (6) | −0.0015 (6) | −0.0103 (7) |
O4w | 0.0391 (9) | 0.0456 (10) | 0.0702 (13) | −0.0063 (8) | 0.0059 (9) | −0.0056 (9) |
N1 | 0.0295 (9) | 0.0320 (9) | 0.0262 (8) | −0.0010 (7) | −0.0012 (7) | −0.0083 (7) |
N2 | 0.0369 (10) | 0.0271 (9) | 0.0435 (11) | 0.0023 (7) | −0.0071 (8) | −0.0133 (8) |
C1 | 0.0481 (13) | 0.0354 (12) | 0.0392 (12) | −0.0015 (10) | −0.0007 (10) | −0.0059 (10) |
C2 | 0.078 (2) | 0.0474 (15) | 0.0445 (15) | −0.0075 (14) | −0.0039 (13) | 0.0094 (12) |
C3 | 0.118 (3) | 0.080 (2) | 0.0274 (13) | −0.022 (2) | −0.0041 (15) | 0.0028 (14) |
C4 | 0.095 (2) | 0.074 (2) | 0.0312 (13) | −0.0206 (17) | 0.0033 (14) | −0.0213 (13) |
C5 | 0.0345 (11) | 0.0449 (12) | 0.0299 (11) | −0.0077 (10) | 0.0018 (9) | −0.0165 (9) |
C6 | 0.0359 (12) | 0.0424 (13) | 0.0433 (13) | −0.0048 (10) | 0.0012 (10) | −0.0241 (10) |
C7 | 0.078 (2) | 0.0630 (19) | 0.0653 (18) | −0.0091 (15) | 0.0051 (15) | −0.0437 (16) |
C8 | 0.096 (3) | 0.056 (2) | 0.109 (3) | 0.0030 (18) | −0.008 (2) | −0.056 (2) |
C9 | 0.090 (2) | 0.0297 (14) | 0.120 (3) | 0.0089 (14) | −0.032 (2) | −0.0280 (17) |
C10 | 0.0677 (18) | 0.0301 (12) | 0.0695 (18) | 0.0032 (12) | −0.0220 (14) | −0.0111 (12) |
C11 | 0.0274 (10) | 0.0267 (10) | 0.0283 (10) | 0.0014 (8) | −0.0010 (8) | −0.0097 (8) |
C12 | 0.0249 (9) | 0.0242 (9) | 0.0247 (9) | 0.0016 (8) | 0.0001 (7) | −0.0074 (7) |
C13 | 0.0230 (9) | 0.0232 (9) | 0.0245 (9) | 0.0027 (7) | −0.0001 (7) | −0.0050 (7) |
C14 | 0.0286 (10) | 0.0270 (10) | 0.0260 (10) | 0.0054 (8) | −0.0053 (8) | −0.0102 (8) |
C15 | 0.0253 (10) | 0.0265 (9) | 0.0255 (9) | 0.0025 (8) | −0.0048 (7) | −0.0067 (8) |
Geometric parameters (Å, º) top
Ni1—N1 | 2.061 (2) | C1—H1 | 0.9300 |
Ni1—N2 | 2.065 (2) | C2—C3 | 1.367 (4) |
Ni1—O1 | 2.052 (1) | C2—H2 | 0.9300 |
Ni1—O1w | 2.075 (2) | C3—C4 | 1.367 (4) |
Ni1—O2w | 2.062 (2) | C3—H3 | 0.9300 |
Ni1—O3w | 2.082 (2) | C4—C5 | 1.379 (3) |
O1—C11 | 1.259 (2) | C4—H4 | 0.9300 |
O2—C11 | 1.251 (2) | C5—C6 | 1.477 (3) |
O3—C14 | 1.243 (3) | C6—C7 | 1.383 (3) |
O4—C14 | 1.258 (2) | C7—C8 | 1.368 (5) |
O1w—H1w1 | 0.844 (9) | C7—H7 | 0.9300 |
O1w—H1w2 | 0.851 (9) | C8—C9 | 1.367 (5) |
O2w—H2w1 | 0.83 (2) | C8—H8 | 0.9300 |
O2w—H2w2 | 0.848 (7) | C9—C10 | 1.384 (4) |
O3w—H3w1 | 0.850 (9) | C9—H9 | 0.9300 |
O3w—H3w2 | 0.844 (9) | C10—H10 | 0.9300 |
O4w—H4w1 | 0.852 (10) | C11—C12 | 1.507 (3) |
O4w—H4w2 | 0.850 (10) | C12—C15i | 1.399 (3) |
N1—C1 | 1.333 (3) | C12—C13 | 1.399 (3) |
N1—C5 | 1.341 (3) | C13—C15 | 1.385 (3) |
N2—C10 | 1.340 (3) | C13—C14 | 1.523 (2) |
N2—C6 | 1.344 (3) | C15—C12i | 1.399 (3) |
C1—C2 | 1.375 (4) | C15—H15 | 0.9300 |
N1—Ni1—N2 | 79.65 (7) | C4—C3—H3 | 120.2 |
N1—Ni1—O1 | 97.78 (6) | C2—C3—H3 | 120.2 |
N1—Ni1—O1w | 176.98 (6) | C3—C4—C5 | 119.4 (3) |
N1—Ni1—O2w | 88.26 (6) | C3—C4—H4 | 120.3 |
N1—Ni1—O3w | 89.09 (6) | C5—C4—H4 | 120.3 |
N2—Ni1—O1 | 176.99 (6) | N1—C5—C4 | 121.1 (2) |
N2—Ni1—O1w | 97.59 (7) | N1—C5—C6 | 115.85 (18) |
N2—Ni1—O2w | 91.80 (7) | C4—C5—C6 | 123.0 (2) |
N2—Ni1—O3w | 86.85 (7) | N2—C6—C7 | 121.5 (2) |
O1—Ni1—O1w | 85.00 (6) | N2—C6—C5 | 115.62 (18) |
O1—Ni1—O2w | 89.71 (6) | C7—C6—C5 | 122.8 (2) |
O1—Ni1—O3w | 91.54 (6) | C8—C7—C6 | 119.1 (3) |
O1w—Ni1—O2w | 90.60 (6) | C8—C7—H7 | 120.4 |
O1w—Ni1—O3w | 92.01 (6) | C6—C7—H7 | 120.4 |
O2w—Ni1—O3w | 177.20 (6) | C9—C8—C7 | 119.8 (3) |
C11—O1—Ni1 | 127.42 (13) | C9—C8—H8 | 120.1 |
Ni1—O1w—H1w1 | 105.1 (17) | C7—C8—H8 | 120.1 |
Ni1—O1w—H1w2 | 115.9 (17) | C8—C9—C10 | 118.7 (3) |
H1w1—O1w—H1w2 | 109.4 (15) | C8—C9—H9 | 120.7 |
Ni1—O2w—H2w1 | 110.0 (17) | C10—C9—H9 | 120.7 |
Ni1—O2w—H2w2 | 116.9 (17) | N2—C10—C9 | 122.1 (3) |
H2w1—O2w—H2w2 | 111.2 (19) | N2—C10—H10 | 119.0 |
Ni1—O3w—H3w1 | 103.0 (16) | C9—C10—H10 | 119.0 |
Ni1—O3w—H3w2 | 121.7 (17) | O2—C11—O1 | 124.51 (18) |
H3w1—O3w—H3w2 | 109.4 (14) | O2—C11—C12 | 118.86 (17) |
H4w1—O4w—H4w2 | 108.3 (15) | O1—C11—C12 | 116.58 (17) |
C1—N1—C5 | 118.85 (19) | C15i—C12—C13 | 119.09 (17) |
C1—N1—Ni1 | 126.66 (15) | C15i—C12—C11 | 119.03 (17) |
C5—N1—Ni1 | 114.49 (14) | C13—C12—C11 | 121.81 (17) |
C10—N2—C6 | 118.7 (2) | C15—C13—C12 | 118.61 (17) |
C10—N2—Ni1 | 126.82 (18) | C15—C13—C14 | 117.91 (16) |
C6—N2—Ni1 | 114.38 (14) | C12—C13—C14 | 123.43 (17) |
N1—C1—C2 | 122.5 (2) | O3—C14—O4 | 125.05 (18) |
N1—C1—H1 | 118.7 | O3—C14—C13 | 117.53 (17) |
C2—C1—H1 | 118.7 | O4—C14—C13 | 117.28 (17) |
C3—C2—C1 | 118.4 (3) | C13—C15—C12i | 122.27 (18) |
C3—C2—H2 | 120.8 | C13—C15—H15 | 118.9 |
C1—C2—H2 | 120.8 | C12i—C15—H15 | 118.9 |
C4—C3—C2 | 119.7 (3) | ||
N1—Ni1—O1—C11 | −72.00 (17) | C10—N2—C6—C7 | 2.1 (4) |
O2w—Ni1—O1—C11 | −160.21 (17) | Ni1—N2—C6—C7 | 179.1 (2) |
O1w—Ni1—O1—C11 | 109.16 (17) | C10—N2—C6—C5 | −177.6 (2) |
O3w—Ni1—O1—C11 | 17.28 (17) | Ni1—N2—C6—C5 | −0.5 (2) |
O1—Ni1—N1—C1 | −2.61 (19) | N1—C5—C6—N2 | 0.0 (3) |
O2w—Ni1—N1—C1 | 86.85 (19) | C4—C5—C6—N2 | 179.7 (2) |
N2—Ni1—N1—C1 | 179.0 (2) | N1—C5—C6—C7 | −179.6 (2) |
O3w—Ni1—N1—C1 | −94.04 (19) | C4—C5—C6—C7 | 0.0 (4) |
O1—Ni1—N1—C5 | 177.79 (14) | N2—C6—C7—C8 | −1.1 (4) |
O2w—Ni1—N1—C5 | −92.74 (15) | C5—C6—C7—C8 | 178.5 (3) |
N2—Ni1—N1—C5 | −0.60 (15) | C6—C7—C8—C9 | −0.6 (5) |
O3w—Ni1—N1—C5 | 86.37 (15) | C7—C8—C9—C10 | 1.3 (6) |
N1—Ni1—N2—C10 | 177.4 (2) | C6—N2—C10—C9 | −1.3 (4) |
O2w—Ni1—N2—C10 | −94.7 (2) | Ni1—N2—C10—C9 | −177.9 (2) |
O1w—Ni1—N2—C10 | −3.9 (2) | C8—C9—C10—N2 | −0.4 (5) |
O3w—Ni1—N2—C10 | 87.8 (2) | Ni1—O1—C11—O2 | 18.2 (3) |
N1—Ni1—N2—C6 | 0.61 (15) | Ni1—O1—C11—C12 | −164.19 (13) |
O2w—Ni1—N2—C6 | 88.52 (16) | O2—C11—C12—C15i | 12.5 (3) |
O1w—Ni1—N2—C6 | 179.36 (15) | O1—C11—C12—C15i | −165.26 (18) |
O3w—Ni1—N2—C6 | −89.03 (16) | O2—C11—C12—C13 | −170.81 (19) |
C5—N1—C1—C2 | −1.0 (4) | O1—C11—C12—C13 | 11.5 (3) |
Ni1—N1—C1—C2 | 179.4 (2) | C15i—C12—C13—C15 | 2.2 (3) |
N1—C1—C2—C3 | −0.5 (4) | C11—C12—C13—C15 | −174.52 (17) |
C1—C2—C3—C4 | 1.8 (5) | C15i—C12—C13—C14 | −174.92 (18) |
C2—C3—C4—C5 | −1.6 (5) | C11—C12—C13—C14 | 8.3 (3) |
C1—N1—C5—C4 | 1.2 (3) | C15—C13—C14—O3 | 71.3 (2) |
Ni1—N1—C5—C4 | −179.2 (2) | C12—C13—C14—O3 | −111.6 (2) |
C1—N1—C5—C6 | −179.1 (2) | C15—C13—C14—O4 | −104.7 (2) |
Ni1—N1—C5—C6 | 0.5 (2) | C12—C13—C14—O4 | 72.5 (2) |
C3—C4—C5—N1 | 0.1 (4) | C12—C13—C15—C12i | −2.3 (3) |
C3—C4—C5—C6 | −179.6 (3) | C14—C13—C15—C12i | 175.01 (18) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O4 | 0.84 (1) | 2.15 (1) | 2.989 (2) | 176 (2) |
O1w—H1w2···O3ii | 0.85 (1) | 1.87 (1) | 2.714 (2) | 174 (2) |
O2w—H2w2···O4ii | 0.85 (1) | 1.90 (1) | 2.737 (2) | 172 (2) |
O2w—H2w1···O4wiii | 0.83 (2) | 1.85 (2) | 2.674 (2) | 178 (2) |
O3w—H3w1···O2 | 0.85 (1) | 1.90 (1) | 2.701 (2) | 156 (2) |
O3w—H3w2···O4iv | 0.84 (1) | 1.93 (1) | 2.746 (2) | 163 (2) |
O4w—H4w1···O2 | 0.85 (1) | 1.83 (1) | 2.676 (2) | 173 (3) |
O4w—H4w2···O3v | 0.85 (1) | 1.96 (1) | 2.781 (3) | 161 (3) |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x−1, y, z; (iv) −x+2, −y+2, −z+1; (v) x+1, y, z. |
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