The title complex, [Ni(C
4H
4O
4S)(C
3H
4N
2)
3]·H
2O, displays a distorted octahedral NiN
3O
2S coordination geometry, formed by three imidazole (imid) ligands and one thiodiacetate dianion. The Ni
II atom is displaced from one of the imid planes, and the angle between the corresponding Ni—N bond and the imid plane is 21.94 (19)°. This spatial orientation is stabilized by an intermolecular C—H
π interaction between one imid ligand and the C—H bond of an adjacent imid ligand.
Supporting information
CCDC reference: 282549
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.111
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni - S .. 7.75 su
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
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Tris(1
H-imidazole-
κN3)(thiodiacetato-
κ3O,
S,
O')nickel(II) monohydrate
top
Crystal data top
[Ni(C4H4O4S)(C3H4N2)3]·H2O | F(000) = 888 |
Mr = 429.10 | Dx = 1.629 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 13236 reflections |
a = 8.2351 (3) Å | θ = 1.6–27.5° |
b = 25.3931 (8) Å | µ = 1.27 mm−1 |
c = 8.6540 (3) Å | T = 295 K |
β = 104.851 (1)° | Platelet, blue |
V = 1749.23 (10) Å3 | 0.33 × 0.31 × 0.03 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4014 independent reflections |
Radiation source: fine-focus sealed tube | 3487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −32→32 |
Tmin = 0.662, Tmax = 0.965 | l = −11→11 |
16127 measured reflections | |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0342P)2 + 2.1571P] where P = (Fo2 + 2Fc2)/3 |
4014 reflections | (Δ/σ)max = 0.001 |
235 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Ni | 0.41452 (4) | 0.130029 (14) | 0.33644 (4) | 0.02661 (12) | |
S | 0.33515 (10) | 0.03583 (3) | 0.30999 (10) | 0.03509 (19) | |
O1W | 0.0451 (6) | 0.04229 (17) | −0.3846 (5) | 0.1084 (15) | |
H1B | 0.0745 | 0.0592 | −0.2975 | 0.080* | |
H1A | 0.0920 | 0.0123 | −0.3750 | 0.080* | |
O1 | 0.6222 (3) | 0.10267 (9) | 0.2736 (3) | 0.0394 (5) | |
O2 | 0.7540 (4) | 0.04258 (11) | 0.1667 (4) | 0.0596 (7) | |
O3 | 0.2877 (3) | 0.12940 (8) | 0.0933 (3) | 0.0399 (5) | |
O4 | 0.0773 (4) | 0.09901 (11) | −0.0956 (3) | 0.0612 (8) | |
C1 | 0.6413 (4) | 0.05646 (13) | 0.2272 (4) | 0.0361 (7) | |
C2 | 0.5187 (5) | 0.01418 (13) | 0.2516 (5) | 0.0467 (9) | |
H2A | 0.5797 | −0.0101 | 0.3323 | 0.056* | |
H2B | 0.4817 | −0.0055 | 0.1526 | 0.056* | |
C3 | 0.1827 (4) | 0.04201 (12) | 0.1195 (4) | 0.0405 (8) | |
H3A | 0.2016 | 0.0139 | 0.0503 | 0.049* | |
H3B | 0.0716 | 0.0369 | 0.1360 | 0.049* | |
C4 | 0.1843 (4) | 0.09406 (12) | 0.0335 (4) | 0.0369 (7) | |
C12 | 0.6880 (4) | 0.11105 (15) | 0.6411 (4) | 0.0464 (8) | |
H12 | 0.7644 | 0.1021 | 0.5828 | 0.056* | |
C15 | 0.5815 (6) | 0.12663 (15) | 0.8436 (5) | 0.0580 (11) | |
H15 | 0.5688 | 0.1306 | 0.9468 | 0.070* | |
C14 | 0.4638 (5) | 0.13375 (15) | 0.7054 (4) | 0.0478 (9) | |
H14 | 0.3533 | 0.1438 | 0.6973 | 0.057* | |
C22 | 0.5628 (6) | 0.23847 (15) | 0.4329 (5) | 0.0553 (10) | |
H22 | 0.5848 | 0.2303 | 0.5410 | 0.066* | |
C25 | 0.5447 (5) | 0.28264 (15) | 0.2175 (6) | 0.0594 (11) | |
H25 | 0.5490 | 0.3098 | 0.1464 | 0.071* | |
C24 | 0.4923 (4) | 0.23283 (14) | 0.1797 (5) | 0.0456 (8) | |
H24 | 0.4555 | 0.2195 | 0.0766 | 0.055* | |
C32 | 0.0538 (5) | 0.13055 (15) | 0.3595 (5) | 0.0478 (9) | |
H32 | 0.0556 | 0.0947 | 0.3812 | 0.057* | |
C35 | −0.0422 (5) | 0.20963 (17) | 0.2965 (5) | 0.0576 (10) | |
H35 | −0.1132 | 0.2385 | 0.2679 | 0.069* | |
C34 | 0.1271 (4) | 0.20966 (14) | 0.3280 (5) | 0.0461 (8) | |
H34 | 0.1932 | 0.2390 | 0.3234 | 0.055* | |
N13 | 0.5300 (3) | 0.12417 (10) | 0.5779 (3) | 0.0345 (6) | |
N11 | 0.7229 (4) | 0.11232 (13) | 0.8005 (4) | 0.0576 (9) | |
H11 | 0.8187 | 0.1053 | 0.8650 | 0.069* | |
N23 | 0.5020 (3) | 0.20510 (10) | 0.3176 (3) | 0.0353 (6) | |
N21 | 0.5893 (5) | 0.28535 (12) | 0.3771 (5) | 0.0634 (10) | |
H21 | 0.6281 | 0.3126 | 0.4333 | 0.076* | |
N33 | 0.1877 (3) | 0.15870 (11) | 0.3687 (4) | 0.0404 (7) | |
N31 | −0.0881 (4) | 0.15934 (14) | 0.3148 (4) | 0.0543 (8) | |
H31 | −0.1891 | 0.1479 | 0.3005 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.02091 (18) | 0.02830 (19) | 0.02816 (19) | −0.00088 (14) | 0.00180 (14) | −0.00315 (15) |
S | 0.0356 (4) | 0.0321 (4) | 0.0351 (4) | −0.0045 (3) | 0.0046 (3) | 0.0037 (3) |
O1W | 0.117 (4) | 0.104 (3) | 0.096 (3) | 0.024 (3) | 0.013 (3) | −0.026 (2) |
O1 | 0.0297 (11) | 0.0365 (12) | 0.0546 (14) | −0.0035 (9) | 0.0158 (11) | −0.0117 (10) |
O2 | 0.0533 (17) | 0.0593 (17) | 0.0744 (19) | 0.0080 (13) | 0.0314 (15) | −0.0150 (14) |
O3 | 0.0479 (14) | 0.0315 (11) | 0.0335 (11) | −0.0044 (10) | −0.0021 (10) | −0.0016 (9) |
O4 | 0.0563 (17) | 0.0534 (16) | 0.0528 (16) | 0.0045 (13) | −0.0244 (13) | 0.0013 (13) |
C1 | 0.0290 (15) | 0.0422 (17) | 0.0341 (16) | 0.0065 (13) | 0.0027 (13) | −0.0001 (14) |
C2 | 0.045 (2) | 0.0330 (17) | 0.060 (2) | 0.0092 (15) | 0.0103 (18) | 0.0044 (16) |
C3 | 0.0370 (18) | 0.0343 (16) | 0.0423 (18) | −0.0075 (13) | −0.0045 (15) | −0.0060 (14) |
C4 | 0.0343 (17) | 0.0321 (15) | 0.0384 (17) | 0.0053 (13) | −0.0015 (14) | −0.0040 (13) |
C12 | 0.0346 (18) | 0.054 (2) | 0.0435 (19) | 0.0031 (15) | −0.0038 (15) | 0.0012 (17) |
C15 | 0.083 (3) | 0.051 (2) | 0.0330 (18) | 0.005 (2) | 0.001 (2) | −0.0001 (16) |
C14 | 0.054 (2) | 0.049 (2) | 0.0381 (18) | 0.0079 (17) | 0.0075 (17) | −0.0027 (16) |
C22 | 0.069 (3) | 0.046 (2) | 0.051 (2) | −0.0198 (19) | 0.017 (2) | −0.0133 (17) |
C25 | 0.052 (2) | 0.0361 (19) | 0.088 (3) | −0.0019 (16) | 0.013 (2) | 0.018 (2) |
C24 | 0.0420 (19) | 0.0442 (18) | 0.0449 (19) | −0.0035 (15) | 0.0009 (16) | 0.0054 (16) |
C32 | 0.0387 (19) | 0.0474 (19) | 0.059 (2) | −0.0018 (15) | 0.0161 (17) | −0.0023 (17) |
C35 | 0.039 (2) | 0.063 (3) | 0.071 (3) | 0.0145 (18) | 0.015 (2) | 0.013 (2) |
C34 | 0.0364 (18) | 0.0455 (19) | 0.057 (2) | 0.0027 (15) | 0.0124 (16) | 0.0074 (17) |
N13 | 0.0283 (13) | 0.0367 (14) | 0.0334 (13) | 0.0000 (10) | −0.0018 (11) | −0.0025 (11) |
N11 | 0.056 (2) | 0.0564 (19) | 0.0419 (17) | 0.0005 (16) | −0.0212 (16) | 0.0043 (15) |
N23 | 0.0348 (14) | 0.0301 (13) | 0.0386 (14) | −0.0040 (11) | 0.0050 (12) | −0.0049 (11) |
N21 | 0.076 (2) | 0.0351 (16) | 0.082 (3) | −0.0193 (16) | 0.025 (2) | −0.0186 (17) |
N33 | 0.0225 (13) | 0.0490 (16) | 0.0482 (16) | −0.0006 (11) | 0.0062 (12) | −0.0088 (13) |
N31 | 0.0259 (14) | 0.068 (2) | 0.070 (2) | −0.0046 (14) | 0.0142 (15) | −0.0105 (18) |
Geometric parameters (Å, º) top
Ni—O1 | 2.044 (2) | C15—N11 | 1.361 (6) |
Ni—O3 | 2.096 (2) | C15—H15 | 0.9300 |
Ni—N13 | 2.067 (3) | C14—N13 | 1.372 (5) |
Ni—N23 | 2.059 (3) | C14—H14 | 0.9300 |
Ni—N33 | 2.089 (3) | C22—N23 | 1.307 (4) |
Ni—S | 2.4748 (8) | C22—N21 | 1.324 (5) |
S—C2 | 1.799 (4) | C22—H22 | 0.9300 |
S—C3 | 1.805 (3) | C25—N21 | 1.337 (6) |
O1W—H1B | 0.8462 | C25—C24 | 1.349 (5) |
O1W—H1A | 0.8480 | C25—H25 | 0.9300 |
O1—C1 | 1.263 (4) | C24—N23 | 1.370 (4) |
O2—C1 | 1.228 (4) | C24—H24 | 0.9300 |
O3—C4 | 1.254 (4) | C32—N33 | 1.300 (4) |
O4—C4 | 1.239 (4) | C32—N31 | 1.348 (5) |
C1—C2 | 1.525 (5) | C32—H32 | 0.9300 |
C2—H2A | 0.9700 | C35—C34 | 1.351 (5) |
C2—H2B | 0.9700 | C35—N31 | 1.353 (5) |
C3—C4 | 1.519 (5) | C35—H35 | 0.9300 |
C3—H3A | 0.9700 | C34—N33 | 1.399 (4) |
C3—H3B | 0.9700 | C34—H34 | 0.9300 |
C12—N13 | 1.318 (4) | N11—H11 | 0.8600 |
C12—N11 | 1.335 (5) | N21—H21 | 0.8600 |
C12—H12 | 0.9300 | N31—H31 | 0.8600 |
C15—C14 | 1.345 (5) | | |
| | | |
O1—Ni—O3 | 88.05 (10) | C14—C15—N11 | 105.3 (3) |
O1—Ni—N13 | 92.58 (10) | C14—C15—H15 | 127.3 |
O1—Ni—N23 | 87.70 (10) | N11—C15—H15 | 127.3 |
O1—Ni—N33 | 172.54 (11) | C15—C14—N13 | 110.3 (4) |
O1—Ni—S | 82.30 (7) | C15—C14—H14 | 124.8 |
O3—Ni—N13 | 174.88 (10) | N13—C14—H14 | 124.8 |
O3—Ni—N23 | 91.26 (10) | N23—C22—N21 | 111.8 (4) |
O3—Ni—N33 | 84.52 (11) | N23—C22—H22 | 124.1 |
O3—Ni—S | 81.26 (6) | N21—C22—H22 | 124.1 |
N13—Ni—N23 | 93.83 (10) | N21—C25—C24 | 106.5 (4) |
N13—Ni—N33 | 94.89 (11) | N21—C25—H25 | 126.7 |
N13—Ni—S | 93.79 (7) | C24—C25—H25 | 126.7 |
N23—Ni—N33 | 91.78 (11) | C25—C24—N23 | 109.1 (4) |
N23—Ni—S | 167.68 (8) | C25—C24—H24 | 125.5 |
N33—Ni—S | 97.19 (8) | N23—C24—H24 | 125.5 |
C2—S—C3 | 102.01 (18) | N33—C32—N31 | 112.3 (3) |
C2—S—Ni | 95.76 (12) | N33—C32—H32 | 123.9 |
C3—S—Ni | 96.08 (10) | N31—C32—H32 | 123.9 |
H1B—O1W—H1A | 110.4 | C34—C35—N31 | 106.4 (3) |
C1—O1—Ni | 125.5 (2) | C34—C35—H35 | 126.8 |
C4—O3—Ni | 122.1 (2) | N31—C35—H35 | 126.8 |
O2—C1—O1 | 124.9 (3) | C35—C34—N33 | 109.5 (3) |
O2—C1—C2 | 117.1 (3) | C35—C34—H34 | 125.3 |
O1—C1—C2 | 118.0 (3) | N33—C34—H34 | 125.3 |
C1—C2—S | 117.2 (2) | C12—N13—C14 | 105.3 (3) |
C1—C2—H2A | 108.0 | C12—N13—Ni | 125.9 (3) |
S—C2—H2A | 108.0 | C14—N13—Ni | 128.7 (2) |
C1—C2—H2B | 108.0 | C12—N11—C15 | 108.5 (3) |
S—C2—H2B | 108.0 | C12—N11—H11 | 125.8 |
H2A—C2—H2B | 107.2 | C15—N11—H11 | 125.8 |
C4—C3—S | 115.6 (2) | C22—N23—C24 | 104.9 (3) |
C4—C3—H3A | 108.4 | C22—N23—Ni | 127.8 (3) |
S—C3—H3A | 108.4 | C24—N23—Ni | 126.9 (2) |
C4—C3—H3B | 108.4 | C22—N21—C25 | 107.7 (3) |
S—C3—H3B | 108.4 | C22—N21—H21 | 126.2 |
H3A—C3—H3B | 107.4 | C25—N21—H21 | 126.2 |
O4—C4—O3 | 123.4 (3) | C32—N33—C34 | 104.5 (3) |
O4—C4—C3 | 115.9 (3) | C32—N33—Ni | 125.0 (2) |
O3—C4—C3 | 120.7 (3) | C34—N33—Ni | 124.2 (2) |
N13—C12—N11 | 110.6 (4) | C32—N31—C35 | 107.3 (3) |
N13—C12—H12 | 124.7 | C32—N31—H31 | 126.3 |
N11—C12—H12 | 124.7 | C35—N31—H31 | 126.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O2i | 0.85 | 2.37 | 3.056 (5) | 138 |
O1W—H1B···O4 | 0.85 | 2.01 | 2.839 (5) | 165 |
N11—H11···O4ii | 0.86 | 2.07 | 2.845 (5) | 149 |
N21—H21···O3iii | 0.86 | 2.21 | 3.048 (4) | 165 |
N21—H21···O4iii | 0.86 | 2.29 | 2.950 (4) | 134 |
N31—H31···O1iv | 0.86 | 1.90 | 2.730 (4) | 163 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z+1; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1, y, z. |