Bis­(di-[mu]-acetato-aqua{2-[N-ethyl-N-(2-hydroxy-4-methyl­benzyl)­amino­methyl]-1-methyl­benz­imid­az­ole}­nickel)­nickel(II) tetra­hy­drate

The previously unknown title compound, tetra-[mu]-ace­tato-1:2[kappa]²O;1:2[kappa]²O:O';­2:3[kappa]²O;­2:3[kappa]²O:O'-di­aqua-1[kappa]O,3[kappa]O-bis­([mu]-2-{[N-ethyl-N-(2-hy­droxy-5-methylbenzyl)­am­ino]­methyl}-1-methyl-1H-benz­imid­az­ole)-1[kappa]³N³,N,O:2[kappa]O;3[kappa]³N³,N,O:2[kappa]O-tri­nickel(II) tetra­hy­drate, [Ni₃(C₁₈H₂₂N₃O)₂(C₂H₃O₂)₄(H₂O)₂]·­4H₂O, (I), is a centrosymmetric linear trinuclear nickel(II) complex, where the Ni atoms are in an octahedral coordination and the ligand heteroatoms act so as to model amino acid residues.

S1. Comment

NO COMMENT

S2. Experimental

1-Methyl-2-{[N-ethyl-N-(2-hydroxy-5-methylbenzyl)amino]methyl}-1H-benzimidazole (L; 0.224 g, 0.725 mmol) dissolved in methanol (7 ml) was added slowly to a suspension of NiBr₂ (0.231 g, 0.966 mmol) in refluxing methanol. Heating was continued until dissolution of the nickel salt was complete, affording a clear green solution. Sodium acetate (0.277 g, 0.203 mmol) dissolved in methanol (5 ml) was added to the green solution. The solvent was removed under vacuum, resulting in a crude green product. This material was dissolved in acetonitrile and the solution filtered and evaporated to dryness. Recrystallization from methanol/2-propanol resulted in crystals of suitable quality for X-ray structure determination.

S3. Refinement

The coordinates of the two H atoms of the water molecule O8 could not be reliably located and were not included in the refinement.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992-1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: Xtal3.4 CRYLSQ (Hall et al., 1995); software used to prepare material for publication: Xtal3.4 BONDLA CIFIO.

(I)

Crystal data

[Ni3(C18H22N3O)2(C2H3O2)4(H2O)2]·4H2O	Z = 1
Mr = 1137.15	F(000) = 598
Triclinic, P1	Dx = 1.419 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 11.130 (2) Å	Cell parameters from 25 reflections
b = 11.732 (2) Å	θ = 17.2–26.1°
c = 12.258 (2) Å	µ = 1.83 mm^−1
α = 99.66 (2)°	T = 193 K
β = 110.34 (1)°	Plate, colourless
γ = 110.23 (1)°	0.12 × 0.12 × 0.02 mm
V = 1330.6 (5) Å^3

Data collection

Rigaku AFC-6R diffractometer	2872 reflections with F > 2.5σ(Fo)'
Radiation source: Rigaku rotating anode	Rint = 0.031
Graphite monochromator	θmax = 60.0°, θmin = 4.1°
ω–2θ scans	h = −11→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
Tmin = 0.873, Tmax = 0.965	l = −13→0
4152 measured reflections	3 standard reflections every 150 reflections
3940 independent reflections	intensity decay: 0.8%

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters not refined
wR(F^2) = 0.047	Weighting scheme based on measured s.u.'s w = 1/σ^2(Fo)
S = 1.93	(Δ/σ)max < 0.001
2865 reflections	Δρmax = 0.64 e Å^−3
322 parameters	Δρmin = −0.68 e Å^−3

Special details

Experimental. The scan width was (1.30 + 0.30tanθ)° with an ω scan speed of 8° per minute (up to 5 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. Data can only be collected to 2theta 120 ° on a AFC6R diffractometer when the evacuated beam tunnel in used. Mass attenuation coefficients for absorption from International Tables for X-ray Crystallography, Vol IV (1974) Table 2.1 C.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.50000	0.50000	0.50000	0.0280 (5)
Ni2	0.22639 (9)	0.43520 (8)	0.27164 (8)	0.0255 (4)
O1	0.2877 (3)	0.4391 (3)	0.4497 (3)	0.0255 (14)
O2	0.4235 (3)	0.4344 (3)	0.3044 (3)	0.0268 (14)
O3	0.4009 (4)	0.3737 (4)	0.1152 (4)	0.054 (2)
O4	0.3253 (4)	0.6325 (3)	0.3253 (3)	0.0318 (14)
O5	0.5077 (4)	0.6745 (3)	0.5028 (3)	0.0317 (14)
O6	0.1834 (4)	0.4333 (3)	0.0903 (3)	0.0351 (15)
O7	0.6989 (5)	0.3011 (4)	0.8865 (4)	0.060 (2)
O8	0.4650 (6)	0.3269 (5)	0.9188 (5)	0.094 (3)
N1	0.0252 (4)	0.4320 (4)	0.2479 (4)	0.0277 (17)
N2	0.1040 (4)	0.2378 (4)	0.2049 (4)	0.0271 (17)
N3	−0.1131 (4)	0.0769 (4)	0.1210 (4)	0.0331 (17)
C1	0.0239 (6)	0.4472 (5)	0.3700 (5)	0.031 (2)
C2	0.0534 (5)	0.3531 (5)	0.4308 (5)	0.026 (2)
C3	−0.0503 (6)	0.2653 (5)	0.4522 (5)	0.034 (2)
C4	−0.0245 (6)	0.1869 (5)	0.5193 (6)	0.038 (2)
C5	0.1137 (7)	0.1984 (5)	0.5673 (6)	0.041 (3)
C6	0.2193 (6)	0.2813 (5)	0.5465 (5)	0.036 (2)
C7	0.1909 (5)	0.3581 (4)	0.4766 (5)	0.027 (2)
C8	−0.1390 (7)	0.0966 (6)	0.5421 (6)	0.058 (3)
C9	0.0038 (6)	0.5371 (5)	0.2030 (5)	0.035 (2)
C10	−0.1321 (6)	0.5488 (5)	0.1896 (5)	0.038 (2)
C11	−0.0900 (6)	0.3038 (5)	0.1578 (5)	0.034 (2)
C12	−0.0324 (6)	0.2073 (5)	0.1631 (5)	0.029 (2)
C13	0.1175 (6)	0.1244 (5)	0.1937 (5)	0.028 (2)
C14	0.2345 (6)	0.0986 (5)	0.2246 (5)	0.034 (2)
C15	0.2117 (6)	−0.0292 (5)	0.1950 (5)	0.041 (3)
C16	0.0735 (7)	−0.1296 (5)	0.1362 (5)	0.040 (2)
C17	−0.0452 (6)	−0.1069 (5)	0.1078 (5)	0.041 (2)
C18	−0.0215 (6)	0.0210 (5)	0.1383 (5)	0.032 (2)
C19	−0.2693 (6)	0.0097 (6)	0.0699 (7)	0.058 (3)
C20	0.4626 (6)	0.3920 (5)	0.2281 (5)	0.032 (2)
C21	0.5876 (6)	0.3604 (5)	0.2738 (5)	0.040 (2)
C22	0.4327 (6)	0.7073 (5)	0.4248 (6)	0.033 (2)
C23	0.4759 (7)	0.8493 (5)	0.4513 (7)	0.060 (3)
H1a	−0.06681	0.43970	0.36020	0.03700*
H1b	0.09490	0.53120	0.42350	0.03700*
H3	−0.14409	0.26000	0.41800	0.04100*
H5	0.13620	0.14750	0.61600	0.05000*
H6	0.31250	0.28630	0.57981	0.04300*
H06a	0.26790	0.42250	0.10041	0.05400*
H06b	0.19770	0.51930	0.08110	0.05400*
H8b	−0.10330	0.04850	0.58800	0.07000*
H8c	−0.21779	0.03950	0.46580	0.07000*
H8a	−0.17050	0.14440	0.58741	0.07000*
H9a	0.00509	0.52391	0.12471	0.04200*
H9b	0.08261	0.61610	0.25940	0.04200*
H10b	−0.21209	0.46881	0.13810	0.04600*
H10c	−0.13060	0.57210	0.26780	0.04600*
H10a	−0.13880	0.61310	0.15250	0.04600*
H11a	−0.12069	0.30931	0.07701	0.04100*
H11b	−0.16751	0.27900	0.17830	0.04100*
H14	0.32801	0.16610	0.26470	0.04000*
H15	0.29090	−0.04889	0.21511	0.04800*
H16	0.06221	−0.21560	0.11590	0.04700*
H17	−0.13810	−0.17500	0.06890	0.04900*
H19b	−0.30200	−0.07760	0.02391	0.06900*
H19c	−0.29709	0.01261	0.13520	0.06900*
H19a	−0.31130	0.05030	0.01741	0.06900*
H21b	0.58490	0.32460	0.33741	0.04900*
H21c	0.67321	0.43560	0.30381	0.04900*
H21a	0.58110	0.29870	0.20761	0.04900*
H23b	0.46200	0.86860	0.37661	0.07300*
H23c	0.57319	0.89540	0.50820	0.07300*
H23a	0.41900	0.87250	0.48430	0.07300*
H7a	0.66025	0.29930	0.80648	0.08600*
H7b	0.61827	0.27783	0.89958	0.08600*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0249 (7)	0.0222 (7)	0.0267 (8)	0.0057 (6)	0.0077 (6)	0.0022 (6)
Ni2	0.0250 (5)	0.0181 (5)	0.0248 (5)	0.0036 (4)	0.0103 (4)	0.0012 (4)
O1	0.025 (2)	0.022 (2)	0.028 (2)	0.0075 (16)	0.0141 (18)	0.0057 (17)
O2	0.021 (2)	0.026 (2)	0.024 (2)	0.0041 (16)	0.0102 (18)	−0.0001 (17)
O3	0.056 (3)	0.085 (3)	0.028 (3)	0.042 (3)	0.018 (2)	0.006 (2)
O4	0.029 (2)	0.021 (2)	0.030 (2)	0.0042 (17)	0.007 (2)	0.0008 (17)
O5	0.028 (2)	0.0202 (19)	0.034 (2)	0.0076 (17)	0.0049 (19)	0.0044 (17)
O6	0.036 (2)	0.031 (2)	0.032 (2)	0.0102 (18)	0.014 (2)	0.0076 (18)
O7	0.072 (3)	0.053 (3)	0.050 (3)	0.024 (3)	0.025 (3)	0.017 (2)
O8	0.112 (5)	0.124 (5)	0.078 (4)	0.067 (4)	0.061 (4)	0.029 (4)
N1	0.031 (3)	0.022 (2)	0.029 (3)	0.010 (2)	0.013 (2)	0.007 (2)
N2	0.027 (3)	0.019 (2)	0.024 (3)	0.003 (2)	0.009 (2)	0.002 (2)
N3	0.026 (2)	0.022 (2)	0.031 (3)	−0.002 (2)	0.009 (2)	−0.002 (2)
C1	0.030 (3)	0.030 (3)	0.029 (3)	0.011 (3)	0.012 (3)	0.002 (3)
C2	0.027 (3)	0.021 (3)	0.024 (3)	0.005 (2)	0.014 (3)	−0.001 (2)
C3	0.032 (3)	0.032 (3)	0.029 (3)	0.010 (3)	0.016 (3)	−0.002 (3)
C4	0.050 (4)	0.026 (3)	0.041 (4)	0.010 (3)	0.030 (3)	0.008 (3)
C5	0.055 (4)	0.031 (3)	0.046 (4)	0.022 (3)	0.029 (3)	0.014 (3)
C6	0.043 (4)	0.036 (3)	0.038 (4)	0.020 (3)	0.026 (3)	0.015 (3)
C7	0.031 (3)	0.018 (3)	0.026 (3)	0.008 (2)	0.014 (3)	−0.004 (2)
C8	0.072 (5)	0.044 (4)	0.070 (5)	0.017 (4)	0.051 (4)	0.019 (4)
C9	0.034 (3)	0.031 (3)	0.037 (4)	0.014 (3)	0.014 (3)	0.007 (3)
C10	0.041 (3)	0.037 (3)	0.041 (4)	0.021 (3)	0.020 (3)	0.013 (3)
C11	0.030 (3)	0.033 (3)	0.028 (3)	0.006 (3)	0.012 (3)	0.002 (3)
C12	0.032 (3)	0.021 (3)	0.024 (3)	0.004 (3)	0.012 (3)	−0.001 (2)
C13	0.035 (3)	0.016 (3)	0.021 (3)	0.001 (2)	0.012 (3)	−0.000 (2)
C14	0.035 (3)	0.023 (3)	0.037 (4)	0.008 (3)	0.015 (3)	0.006 (3)
C15	0.054 (4)	0.036 (3)	0.037 (4)	0.025 (3)	0.018 (3)	0.015 (3)
C16	0.052 (4)	0.016 (3)	0.033 (4)	0.005 (3)	0.012 (3)	0.001 (3)
C17	0.046 (4)	0.022 (3)	0.031 (4)	−0.002 (3)	0.011 (3)	−0.000 (3)
C18	0.034 (3)	0.025 (3)	0.026 (3)	0.006 (3)	0.009 (3)	0.003 (3)
C19	0.034 (4)	0.042 (4)	0.068 (5)	−0.003 (3)	0.016 (4)	0.003 (4)
C20	0.029 (3)	0.029 (3)	0.032 (4)	0.004 (3)	0.015 (3)	0.006 (3)
C21	0.035 (3)	0.045 (4)	0.040 (4)	0.015 (3)	0.022 (3)	0.006 (3)
C22	0.031 (3)	0.025 (3)	0.041 (4)	0.010 (3)	0.019 (3)	0.009 (3)
C23	0.048 (4)	0.019 (3)	0.074 (5)	0.010 (3)	−0.003 (4)	0.002 (3)

Geometric parameters (Å, º)

Ni1—O5	2.014 (4)	C5—H5	0.946 (7)
Ni1—O5^i	2.014 (4)	C5—C6	1.376 (10)
Ni1—O1^i	2.036 (4)	C6—H6	0.950 (7)
Ni1—O1	2.036 (4)	C6—C7	1.383 (9)
Ni1—O2^i	2.138 (4)	C8—H8b	0.948 (8)
Ni1—O2	2.138 (4)	C8—H8c	0.952 (5)
Ni2—O1	2.035 (4)	C8—H8a	0.955 (9)
Ni2—O4	2.056 (3)	C9—H9a	0.951 (7)
Ni2—N2	2.073 (4)	C9—H9b	0.952 (4)
Ni2—O2	2.092 (4)	C9—C10	1.521 (10)
Ni2—O6	2.099 (4)	C10—H10c	0.944 (7)
Ni2—N1	2.142 (5)	C10—H10b	0.951 (4)
O1—C7	1.348 (7)	C10—H10a	0.955 (7)
O2—C20	1.260 (9)	C11—H11b	0.945 (7)
O3—C20	1.254 (7)	C11—H11a	0.950 (6)
O4—C22	1.260 (5)	C11—C12	1.482 (9)
O5—C22	1.245 (8)	C13—C14	1.378 (9)
O6—H06a	0.961 (5)	C13—C18	1.421 (6)
O6—H06b	0.998 (4)	C14—H14	0.947 (5)
O7—H7a	0.917 (5)	C14—C15	1.391 (9)
O7—H7b	0.922 (6)	C15—H15	0.949 (8)
N1—C1	1.483 (8)	C15—C16	1.402 (7)
N1—C9	1.490 (8)	C16—H16	0.949 (6)
N1—C11	1.500 (5)	C16—C17	1.375 (11)
N2—C12	1.310 (7)	C17—H17	0.945 (5)
N2—C13	1.380 (8)	C17—C18	1.390 (8)
N3—C18	1.368 (9)	C19—H19b	0.951 (6)
N3—C12	1.370 (6)	C19—H19c	0.953 (9)
N3—C19	1.472 (7)	C19—H19a	0.953 (8)
C1—H1a	0.945 (7)	C20—C21	1.507 (10)
C1—H1b	0.954 (4)	C21—H21c	0.942 (5)
C1—C2	1.496 (9)	C21—H21b	0.950 (7)
C2—C3	1.393 (8)	C21—H21a	0.955 (7)
C2—C7	1.412 (8)	C22—C23	1.506 (8)
C3—H3	0.955 (6)	C23—H23c	0.946 (5)
C3—C4	1.371 (9)	C23—H23a	0.949 (9)
C4—C5	1.389 (10)	C23—H23b	0.953 (8)
C4—C8	1.496 (10)
O5—Ni1—O5^i	180.0000	C5—C6—C7	120.4 (6)
O5—Ni1—O1^i	93.77 (15)	O1—C7—C6	123.9 (5)
O5—Ni1—O1	86.23 (15)	O1—C7—C2	117.3 (5)
O5—Ni1—O2^i	87.40 (15)	C6—C7—C2	118.8 (6)
O5—Ni1—O2	92.60 (15)	H8b—C8—H8c	109.4 (6)
O5^i—Ni1—O1^i	86.23 (15)	H8b—C8—H8a	109.2 (8)
O5^i—Ni1—O1	93.77 (15)	H8b—C8—C4	109.9 (7)
O5^i—Ni1—O2^i	92.60 (15)	H8c—C8—H8a	108.8 (8)
O5^i—Ni1—O2	87.40 (15)	H8c—C8—C4	109.9 (7)
O1^i—Ni1—O1	180.0000	H8a—C8—C4	109.6 (6)
O1^i—Ni1—O2^i	80.99 (15)	H9a—C9—H9b	109.1 (6)
O1^i—Ni1—O2	99.01 (15)	H9a—C9—N1	107.3 (6)
O1—Ni1—O2^i	99.01 (15)	H9a—C9—C10	108.3 (5)
O1—Ni1—O2	80.99 (15)	H9b—C9—N1	107.3 (5)
O2^i—Ni1—O2	180.0000	H9b—C9—C10	108.0 (6)
O1—Ni2—O4	91.58 (14)	N1—C9—C10	116.7 (5)
O1—Ni2—N2	92.33 (16)	H10c—C10—H10b	110.0 (7)
O1—Ni2—O2	82.14 (16)	H10c—C10—H10a	109.5 (7)
O1—Ni2—O6	174.29 (18)	H10c—C10—C9	109.9 (5)
O1—Ni2—N1	94.44 (18)	H10b—C10—H10a	109.0 (5)
O4—Ni2—N2	172.96 (18)	H10b—C10—C9	109.3 (6)
O4—Ni2—O2	88.72 (15)	H10a—C10—C9	109.1 (6)
O4—Ni2—O6	87.65 (15)	H11b—C11—H11a	110.0 (5)
O4—Ni2—N1	92.56 (17)	H11b—C11—C12	109.5 (6)
N2—Ni2—O2	97.61 (18)	H11b—C11—N1	109.7 (5)
N2—Ni2—O6	89.04 (16)	H11a—C11—C12	109.3 (6)
N2—Ni2—N1	81.30 (18)	H11a—C11—N1	109.4 (5)
O2—Ni2—O6	92.18 (17)	C12—C11—N1	109.0 (4)
O2—Ni2—N1	176.38 (19)	N2—C12—N3	111.8 (5)
O6—Ni2—N1	91.25 (18)	N2—C12—C11	123.1 (4)
C7—O1—Ni2	117.5 (3)	N3—C12—C11	125.0 (5)
C7—O1—Ni1	135.6 (4)	C14—C13—N2	132.4 (4)
Ni2—O1—Ni1	98.05 (19)	C14—C13—C18	119.6 (5)
C20—O2—Ni2	128.7 (3)	N2—C13—C18	108.1 (5)
C20—O2—Ni1	137.6 (4)	H14—C14—C13	120.9 (6)
Ni2—O2—Ni1	93.17 (18)	H14—C14—C15	120.8 (7)
C22—O4—Ni2	126.7 (4)	C13—C14—C15	118.3 (5)
C22—O5—Ni1	130.5 (3)	H15—C15—C14	119.6 (5)
H06a—O6—H06b	108.7 (4)	H15—C15—C16	119.3 (6)
H06a—O6—Ni2	89.0 (3)	C14—C15—C16	121.1 (7)
H06b—O6—Ni2	112.5 (3)	H16—C16—C17	119.5 (5)
H7a—O7—H7b	99.5 (4)	H16—C16—C15	118.6 (7)
C1—N1—C9	109.9 (5)	C17—C16—C15	121.9 (6)
C1—N1—C11	110.0 (4)	H17—C17—C16	121.6 (6)
C1—N1—Ni2	106.6 (3)	H17—C17—C18	121.8 (7)
C9—N1—C11	110.1 (4)	C16—C17—C18	116.6 (5)
C9—N1—Ni2	112.1 (4)	N3—C18—C17	131.9 (5)
C11—N1—Ni2	108.1 (4)	N3—C18—C13	105.7 (5)
C12—N2—C13	107.0 (4)	C17—C18—C13	122.4 (6)
C12—N2—Ni2	111.8 (4)	H19b—C19—H19c	109.2 (7)
C13—N2—Ni2	141.1 (4)	H19b—C19—H19a	109.3 (6)
C18—N3—C12	107.4 (4)	H19b—C19—N3	109.9 (7)
C18—N3—C19	126.4 (5)	H19c—C19—H19a	109.0 (8)
C12—N3—C19	126.2 (6)	H19c—C19—N3	109.7 (5)
H1a—C1—H1b	109.6 (7)	H19a—C19—N3	109.7 (6)
H1a—C1—N1	107.9 (5)	O3—C20—O2	122.7 (6)
H1a—C1—C2	107.9 (6)	O3—C20—C21	118.4 (7)
H1b—C1—N1	107.6 (5)	O2—C20—C21	118.9 (5)
H1b—C1—C2	107.6 (5)	H21c—C21—H21b	110.1 (5)
N1—C1—C2	116.1 (5)	H21c—C21—H21a	109.7 (7)
C3—C2—C7	118.2 (5)	H21c—C21—C20	109.7 (6)
C3—C2—C1	121.1 (6)	H21b—C21—H21a	109.1 (7)
C7—C2—C1	120.5 (5)	H21b—C21—C20	109.0 (7)
H3—C3—C4	118.7 (6)	H21a—C21—C20	109.3 (5)
H3—C3—C2	117.8 (6)	O5—C22—O4	125.9 (5)
C4—C3—C2	123.5 (6)	O5—C22—C23	116.8 (4)
C3—C4—C5	116.5 (6)	O4—C22—C23	117.3 (6)
C3—C4—C8	121.3 (6)	H23c—C23—H23a	110.0 (7)
C5—C4—C8	122.2 (6)	H23c—C23—H23b	109.5 (7)
H5—C5—C6	118.7 (7)	H23c—C23—C22	109.4 (7)
H5—C5—C4	119.0 (7)	H23a—C23—H23b	109.3 (7)
C6—C5—C4	122.4 (6)	H23a—C23—C22	109.5 (6)
H6—C6—C5	120.4 (7)	H23b—C23—C22	109.2 (6)
H6—C6—C7	119.2 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.