Tris(1H-imidazole-κN³)(thio­diacetato-κ³O,S,O′)nickel(II) monohydrate

The title complex, [Ni(C₄H₄O₄S)(C₃H₄N₂)₃]·H₂O, displays a distorted octa­hedral NiN₃O₂S 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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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Computing details

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(1H-imidazole-κN³)(thiodiacetato-κ³O,S,O')nickel(II) monohydrate

Crystal data

[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) Å^3	0.33 × 0.31 × 0.03 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0342P)^2 + 2.1571P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2^i	0.85	2.37	3.056 (5)	138
O1W—H1B···O4	0.85	2.01	2.839 (5)	165
N11—H11···O4^ii	0.86	2.07	2.845 (5)	149
N21—H21···O3^iii	0.86	2.21	3.048 (4)	165
N21—H21···O4^iii	0.86	2.29	2.950 (4)	134
N31—H31···O1^iv	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.