Bis[μ2-2,2′-dimethyl-N,N′-bis­(2-oxido­benz­yl)propane-1,3-diamine]-1κ4O,N,N′,O′:2κ2O,O′;2κ2O,O′:3κ4O,N,N′,O′-bis­(N,N′-dimethyl­formamide)-1κO,3κO-di-μ2-formato-1:2κ2O:O′;2:3κ2O:O′-trinickel(II)

Tatar Yıldırım, L.; Atakol, O.; Kavak, G.

doi:10.1107/S1600536807040184

Bis[μ₂-2,2′-dimethyl-N,N′-bis(2-oxidobenzyl)propane-1,3-diamine]-1κ⁴O,N,N′,O′:2κ²O,O′;2κ²O,O′:3κ⁴O,N,N′,O′-bis(N,N′-dimethylformamide)-1κO,3κO-di-μ₂-formato-1:2κ²O:O′;2:3κ²O:O′-trinickel(II)

L. Tatar Yıldırım, O. Atakol and G. Kavak

The title crystal structure, [Ni₃(C₁₉H₂₄N₂O₂)₂(CHO₂)₂(C₃H₇NO)₂], consists of discrete centrosymmetric homotrinuclear nickel complex molecules. In each molecule, the central Ni^II ion is in a distorted octahedral coordination environment, formed by four O atoms from two chelating DML²⁻ ligands [DMLH₂ = N,N′-bis(salicylidene)-2,2′-dimethyl-1,3-propanediamine] in the equatorial plane and two O atoms of two symmetry-related formate ligands in the axial positions. The terminal Ni^II ions also have distorted octahedral coordination environments and these are formed by two O and N atoms from chelating DML²⁻ ligands in the equatorial plane; the axial positions are occupied by O atoms from a dimethylformamide ligand and a formate ligand. The overall result is three edge-shared octahedra in which the closest Ni

Ni distance is 3.0857 (14) Å. The crystal structure is stabilized by weak C—H

O hydrogen bonds (agnostic interactions).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040184/lh2472sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040184/lh2472Isup2.hkl Contains datablock I

CCDC reference: 660154

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.056
wR factor = 0.150
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...         10
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.52 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT245_ALERT_2_C U(iso) H8A     Smaller than U(eq) C8      by ...       0.01 AngSq
PLAT245_ALERT_2_C U(iso) H21     Smaller than U(eq) C21     by ...       0.01 AngSq
PLAT245_ALERT_2_C U(iso) H23B    Smaller than U(eq) C23     by ...       0.03 AngSq
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C22
PLAT390_ALERT_3_C Deviating Methyl C23     X-C-H Bond Angle ......     119.00 Deg.
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1N    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2N    ...          ?
PLAT731_ALERT_1_C Bond    Calc     0.89(4), Rep   0.892(19) ......       2.11 su-Ra
              N2   -H2N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.88(5), Rep   0.890(19) ......       2.63 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.89(4), Rep   0.886(19) ......       2.11 su-Ra
              C20  -H20     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.96000, Rep    0.957(7) ......  Senseless su
              C23  -H23B    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.01000, Rep    1.014(8) ......  Senseless su
              C23  -H23C    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.00000, Rep    0.996(7) ......  Senseless su
              C23  -H23A    1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      119.00, Rep    118.9(7) ......  Senseless su
              N3   -C23  -H23B    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      106.00, Rep    105.7(6) ......  Senseless su
              N3   -C23  -H23C    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      102.00, Rep    102.5(6) ......  Senseless su
              H23B -C23  -H23C    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      110.00, Rep    110.0(6) ......  Senseless su
              N3   -C23  -H23A    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      108.00, Rep    107.9(7) ......  Senseless su
              H23B -C23  -H23A    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      112.00, Rep    111.6(8) ......  Senseless su
              H23C -C23  -H23A    1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of N1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          S
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       1.79
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  26 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

ONNO type Schiff base ligands have been known since as early as 1946 (Barkelew & Calvin, 1946; Martell et al., 1958). Schiff-bases have played an important role in the development of coordination chemistry as they readily form stable complexes with most transition metals (Drew et al., 1985; Fukuhara et al., 1990). Oxygen-bridged polynuclear complexes of the transition series are of interest because of their magnetic properties (Barandika et al., 1999; Ribas et al., 1999; Du et al., 2005). The ONNO type ligand stereochemistry around the metal ions and the structure of the O-atom bridges influence the magnetic exchange interactions. These complexes may be homo or heteronuclear. Polynuclear metal complexes of Schiff-base ligands have been the subject on considerable interest in our laboratory, e.g. [NiZnI₂(LH₂)(dmf)] (Tatar, 2002), [Ni{Ni(LH₂)(O₂CMe)(dmf)}₂] (Tatar & Atakol, 2002), [Ni(LH₂)N₃(dmf)H₂O and Ni(DMLH₂)N₃(dmf)] (Durmuş et al., 2005). Where LH₂ is N,N'-bis(salicylidene)-1,3-propanediamine.

In this study, bis-N,N'(salicylidene)-2,2'-dimethyl-1,3-propanediamine was reduced by using NaBH₄ in MeOH and we obtained an ONNO type ligand. The title molecule was prepared by initating a reaction between the ONNO ligand and nickel(II)-formato in dmf. The crystal and molecular structure of the title homotrinuclear complex has been determined. Recently details of a similar complex were reported literature (Reglinski et al., 2006).

In the title complex (Fig. 1), the central Ni1 atom, which is located on an inversion centre, has a distorted octahedral coordination environment, formed by four O atoms from two DMLH₂ ligands in the equatorial plane [Ni1—O1 = 2.075 (3), Ni1—O2 = 2.076 (3) Å] and two O atoms of two –O₂CH groups located at the axial positions [Ni1—O4 = 2.160 (3) Å]. The bond angles around Ni1 angles range between 99.66 (12) and 80.34 (12)°.

The terminal Ni2 atoms also have distorted octahedral coordination environments formed by two O and two N atoms from DMLH₂ ligands in the equatorial plane and bond distances ranging between 2.037 (3) - 2.098 (4) Å. The distance of atom Ni2 from the O1/O2/N1/N2 mean plane is 0.0546 (8) Å. The dihedral angle between the planes O1—Ni2—O2 and N1—Ni2—N2 is 4.3 (2)°. The axial positions are occupied by atoms O3 and O5ⁱ [symmetry code: (i) -x, -y, -z] from a dmf molecule and an –O₂CH group, respectively. This coordination involves a fairly long axial Ni2—O3 bond of 2.147 (3) Å. The Ni2 coordination involves bond angles ranging between 81.85 (12) and 93.54 (16)°.

The conformation of the rings in the title molecule were analyzed using PLATON (Spek, 2003). The Cremer & Pople puckering parameter (Cremer & Pople, 1975) of Q(2) = 0.262 (2) Å is for the Ni1—O1—Ni2—O2 ring and the dihedral angle between the planes O1—Ni1—O2 and O1—Ni2—O2 is 19.36 (12)°. The six-membered Ni2/N1/C8/C9/C12/N2 ring is in a (C) chair form (Q = 0.607 (6) Å, θ = 3.1 (5)° and φ = 168 (10)°). The Cremer & Pople puckering parameters of the Ni1—O1—Ni2—O5ⁱ—C20ⁱ—O4ⁱ (symmetry code: (i) -x, -y, -z) ring are Q = 1.045 (3) Å, θ = 128.4 (2), φ = 239.7 (3) °, showing this six-membered ring is an E (envelope) form. The crystal structure is stabilized by weak C—H···O hydrogen bonds.

Related literature top

For general background, see: Martell & Calvin (1958); Drew et al. (1985); Fukuhara et al. (1990); Barandika et al. (1999). For related literature, see: Tatar (2002); Tatar & Atakol (2002); Durmuş et al. (2005). For related literature, see: Barkelew & Calvin (1946); Cremer & Pople (1975); Du et al. (2005); Reglinski et al. (2006); Ribas et al. (1999); Spek (2003).

Experimental top

Bis-N,N'(salicylidene)-2,2'-dimethyl-1,3-propanediamine was synthesized from salicylaldehyde and 2,2'-dimethyl-1,3-propanediamine in EtOH. This compound was reduced using NaBH₄ in MeOH resulting in the formation of bis-N,N'(2-hydroxybenzyl)-2,2'-dimethyl-1,3-propanediamine. 0.628 g (2 mmol) bis-N,N'(2-hydroxybenzyl)-2,2'-dimethyl-1,3-propanediamine was dissolved in 50 ml dmf and heated to 383 K. To this solution were added a solution of 0.712 g (3 mmol) NiCl₂.6H₂O in 20 ml hot MeOH and a solution of 0.408 g (6 mmol) NaHCOO in 5 ml hot water. This final mixture was left to stand for 2–3 days. After this period, light green crystals were filtered and dried in air. [C₄₆H₆₄N₆O₁₀Ni₃] Element Analysis results: Ni, found %: 16.24 (calculated %:16.65); N found %: 7.53 (calculated %: 7.94). The measured dmf mass using thermogravimetrie: % 13.69 (calculated: %13.80).

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level (symmetry code (i): -x, -y, -z).

Bis[µ₂-2,2'-dimethyl-N,N'-bis(2-oxidobenzyl)propane-1,3-diamine]- 1κ⁴O,N,N',O':2κ²O,O';2κ²O,O':3κ⁴O,N,N',O'-bis(N,N'- dimethylformamide)-1κO,3κO-di-µ₂-formato-1:2κ²O:O';2:3κ²O:O'- trinickel(II) top

Crystal data top

[Ni₃(C₁₉H₂₄N₂O₂)₂(CHO₂)₂(C₃H₇NO)₂]	F(000) = 1092
M_r = 1037.10	D_x = 1.440 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 15 reflections
a = 10.289 (2) Å	θ = 19.0–23.9°
b = 14.054 (5) Å	µ = 1.88 mm⁻¹
c = 17.005 (4) Å	T = 293 K
β = 103.433 (19)°	Prism, light green
V = 2391.7 (11) Å³	0.2 × 0.2 × 0.1 mm
Z = 2

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	2200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 73.9°, θ_min = 4.1°
non–profiled ω scans	h = −12→0
Absorption correction: ψ scan (North et al., 1968)	k = −17→0
T_min = 0.720, T_max = 0.828	l = −20→21
5007 measured reflections	3 standard reflections every 120 min
4740 independent reflections	intensity decay: 2%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0515P)² + 0.3344P] where P = (F_o² + 2F_c²)/3
4740 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.43 e Å⁻³
6 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Ni₃(C₁₉H₂₄N₂O₂)₂(CHO₂)₂(C₃H₇NO)₂]	V = 2391.7 (11) Å³
M_r = 1037.10	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.289 (2) Å	µ = 1.88 mm⁻¹
b = 14.054 (5) Å	T = 293 K
c = 17.005 (4) Å	0.2 × 0.2 × 0.1 mm
β = 103.433 (19)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	2200 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.048
T_min = 0.720, T_max = 0.828	3 standard reflections every 120 min
5007 measured reflections	intensity decay: 2%
4740 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	6 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.43 e Å⁻³
4740 reflections	Δρ_min = −0.49 e Å⁻³
343 parameters

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	U_iso*/U_eq
Ni1	0	0	0	0.0447 (3)
Ni2	0.00481 (8)	−0.08187 (5)	0.16902 (5)	0.0439 (3)
O1	0.1113 (3)	0.0124 (2)	0.11806 (18)	0.0470 (9)
O3	0.1641 (3)	−0.1840 (2)	0.1868 (2)	0.0510 (9)
O2	−0.0683 (3)	−0.1191 (2)	0.05036 (17)	0.0443 (9)
N2	−0.1059 (4)	−0.1871 (3)	0.2102 (2)	0.0436 (11)
N1	0.0996 (5)	−0.0405 (3)	0.2869 (3)	0.0537 (12)
O4	0.1491 (3)	−0.0798 (2)	−0.0429 (2)	0.0526 (10)
C12	−0.1609 (7)	−0.1579 (5)	0.2788 (4)	0.0598 (17)
C7	0.1727 (8)	0.0507 (4)	0.2844 (4)	0.0646 (19)
C1	0.2388 (6)	0.0303 (3)	0.1530 (3)	0.0480 (14)
C5	0.4122 (7)	0.0612 (4)	0.2736 (4)	0.078 (2)
H5	0.4371	0.0723	0.329	0.093*
C2	0.3375 (6)	0.0313 (4)	0.1086 (4)	0.0641 (16)
H2	0.3148	0.0228	0.0529	0.077*
C6	0.2769 (6)	0.0465 (4)	0.2373 (3)	0.0568 (15)
C18	−0.0554 (5)	−0.2520 (4)	−0.0358 (3)	0.0610 (16)
H18	−0.0156	−0.2155	−0.0693	0.073*
C15	−0.1814 (6)	−0.3629 (4)	0.0580 (3)	0.0604 (16)
H15	−0.2243	−0.4002	0.0894	0.072*
C14	−0.1610 (5)	−0.2665 (4)	0.0757 (3)	0.0477 (14)
C17	−0.0766 (6)	−0.3480 (4)	−0.0512 (3)	0.0668 (17)
H17	−0.0477	−0.3757	−0.0938	0.08*
C19	−0.0936 (5)	−0.2091 (4)	0.0301 (3)	0.0427 (13)
C9	−0.0597 (6)	−0.1276 (4)	0.3550 (3)	0.0614 (16)
O5	0.1429 (4)	−0.0182 (3)	−0.1667 (2)	0.0607 (11)
N3	0.3568 (5)	−0.2094 (3)	0.1475 (3)	0.0568 (12)
C21	0.2270 (6)	−0.1944 (4)	0.1348 (4)	0.0522 (15)
C22	0.4387 (6)	−0.2064 (4)	0.2286 (3)	0.080 (2)
H22A	0.53	−0.2185	0.2274	0.12*
H22B	0.4088	−0.254	0.2608	0.12*
H22C	0.4317	−0.1447	0.2515	0.12*
C13	−0.2127 (5)	−0.2229 (4)	0.1423 (4)	0.0529 (15)
C10	0.0391 (6)	−0.2081 (4)	0.3851 (3)	0.0689 (18)
H10A	0.1026	−0.1879	0.433	0.103*
H10B	0.0853	−0.2242	0.344	0.103*
H10C	−0.0084	−0.2628	0.3974	0.103*
C11	−0.1416 (7)	−0.1071 (4)	0.4189 (4)	0.099 (2)
H11A	−0.0824	−0.0878	0.4687	0.148*
H11B	−0.1884	−0.1637	0.4279	0.148*
H11C	−0.2048	−0.0573	0.3998	0.148*
C3	0.4713 (6)	0.0452 (4)	0.1494 (5)	0.078 (2)
H3	0.5367	0.0444	0.1197	0.094*
C8	0.0105 (7)	−0.0342 (5)	0.3429 (3)	0.0639 (17)
C16	−0.1395 (6)	−0.4034 (4)	−0.0046 (4)	0.0730 (19)
H16	−0.1534	−0.4678	−0.0157	0.088*
C4	0.5093 (7)	0.0599 (4)	0.2304 (5)	0.084 (2)
H4	0.5987	0.0688	0.2559	0.101*
C23	0.4236 (7)	−0.2142 (6)	0.0815 (4)	0.089 (2)
C20	0.1795 (6)	−0.0748 (4)	−0.1089 (4)	0.0565 (15)
H12B	−0.208 (5)	−0.207 (3)	0.295 (3)	0.061*
H13B	−0.274 (4)	−0.273 (3)	0.163 (2)	0.052*
H12A	−0.221 (5)	−0.099 (4)	0.262 (3)	0.067 (17)*
H8A	−0.066 (4)	0.011 (3)	0.321 (3)	0.052*
H7A	0.097 (5)	0.092 (4)	0.259 (3)	0.070 (19)*
H8B	0.064 (4)	−0.021 (3)	0.3945 (17)	0.067 (18)*
H21	0.188 (4)	−0.190 (3)	0.0823 (13)	0.042 (15)*
H7B	0.206 (5)	0.073 (4)	0.342 (3)	0.09 (2)*
H13A	−0.261 (4)	−0.166 (2)	0.121 (3)	0.075 (19)*
H23B	0.4846	−0.2653	0.0803	0.057 (16)*
H23C	0.4841	−0.1563	0.0878	0.09 (2)*
H23A	0.3565	−0.2136	0.0288	0.12 (3)*
H20	0.246 (4)	−0.114 (3)	−0.113 (3)	0.067 (19)*
H2N	−0.042 (3)	−0.230 (3)	0.227 (3)	0.051 (16)*
H1N	0.153 (5)	−0.090 (3)	0.300 (3)	0.09 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0489 (8)	0.0389 (7)	0.0441 (7)	−0.0022 (6)	0.0061 (6)	0.0071 (6)
Ni2	0.0512 (5)	0.0374 (5)	0.0416 (5)	−0.0010 (4)	0.0078 (4)	0.0018 (4)
O1	0.049 (2)	0.045 (2)	0.043 (2)	−0.0099 (18)	0.0016 (17)	0.0045 (16)
O3	0.054 (2)	0.045 (2)	0.055 (2)	0.0034 (18)	0.0129 (19)	0.0038 (18)
O2	0.058 (2)	0.0333 (19)	0.0393 (19)	−0.0065 (17)	0.0076 (17)	0.0044 (15)
N2	0.046 (3)	0.045 (3)	0.040 (3)	0.004 (2)	0.009 (2)	0.004 (2)
N1	0.079 (4)	0.035 (3)	0.045 (3)	−0.002 (3)	0.010 (3)	0.000 (2)
O4	0.056 (2)	0.051 (2)	0.052 (2)	0.0104 (19)	0.0147 (19)	0.0130 (19)
C12	0.079 (5)	0.051 (4)	0.058 (4)	0.007 (4)	0.034 (4)	0.009 (3)
C7	0.100 (6)	0.038 (3)	0.047 (4)	−0.009 (4)	0.000 (4)	−0.002 (3)
C1	0.054 (4)	0.028 (3)	0.057 (4)	−0.004 (3)	0.003 (3)	0.003 (3)
C5	0.085 (5)	0.050 (4)	0.075 (5)	−0.031 (4)	−0.029 (4)	0.007 (3)
C2	0.055 (4)	0.054 (4)	0.078 (4)	−0.014 (3)	0.006 (4)	−0.001 (3)
C6	0.076 (5)	0.036 (3)	0.052 (4)	−0.012 (3)	0.002 (3)	0.004 (3)
C18	0.072 (4)	0.059 (4)	0.050 (3)	−0.008 (3)	0.009 (3)	−0.004 (3)
C15	0.069 (4)	0.049 (4)	0.051 (4)	−0.017 (3)	−0.010 (3)	0.010 (3)
C14	0.053 (3)	0.043 (3)	0.041 (3)	−0.006 (3)	−0.002 (3)	0.001 (3)
C17	0.085 (5)	0.055 (4)	0.057 (4)	−0.006 (4)	0.010 (3)	−0.015 (3)
C19	0.041 (3)	0.041 (3)	0.040 (3)	−0.001 (3)	−0.004 (2)	0.005 (3)
C9	0.088 (5)	0.056 (4)	0.047 (4)	0.006 (4)	0.029 (3)	−0.003 (3)
O5	0.074 (3)	0.058 (3)	0.056 (2)	0.016 (2)	0.027 (2)	0.015 (2)
N3	0.053 (3)	0.049 (3)	0.062 (3)	0.007 (2)	0.000 (3)	−0.005 (2)
C21	0.057 (4)	0.045 (3)	0.049 (4)	0.006 (3)	−0.001 (3)	−0.001 (3)
C22	0.067 (4)	0.077 (5)	0.081 (5)	−0.001 (4)	−0.016 (4)	−0.008 (4)
C13	0.042 (3)	0.058 (4)	0.057 (4)	−0.013 (3)	0.007 (3)	0.013 (3)
C10	0.095 (5)	0.053 (4)	0.049 (4)	0.003 (4)	−0.003 (3)	0.010 (3)
C11	0.175 (7)	0.073 (5)	0.073 (5)	0.012 (5)	0.076 (5)	0.001 (4)
C3	0.059 (5)	0.058 (4)	0.114 (6)	−0.012 (3)	0.014 (4)	−0.002 (4)
C8	0.101 (5)	0.057 (4)	0.034 (4)	0.006 (4)	0.016 (4)	−0.003 (3)
C16	0.101 (5)	0.036 (4)	0.066 (4)	−0.007 (3)	−0.012 (4)	−0.002 (3)
C4	0.064 (5)	0.058 (5)	0.113 (6)	−0.020 (4)	−0.016 (4)	0.008 (4)
C23	0.059 (4)	0.121 (7)	0.090 (6)	0.018 (5)	0.025 (4)	−0.030 (4)
C20	0.046 (4)	0.051 (4)	0.075 (5)	0.010 (3)	0.021 (3)	0.003 (4)

Geometric parameters (Å, º) top

Ni1—Ni2	3.0857 (14)	C18—H18	0.93
Ni1—O1ⁱ	2.075 (3)	C15—C16	1.362 (7)
Ni1—O1	2.075 (3)	C15—C14	1.392 (7)
Ni1—O2	2.076 (3)	C15—H15	0.93
Ni1—O2ⁱ	2.076 (3)	C14—C19	1.409 (6)
Ni1—O4	2.160 (3)	C14—C13	1.490 (7)
Ni1—O4ⁱ	2.160 (3)	C17—C16	1.375 (7)
Ni2—O1	2.037 (3)	C17—H17	0.93
Ni2—O2	2.051 (3)	C9—C10	1.529 (7)
Ni2—O5ⁱ	2.064 (4)	C9—C8	1.534 (8)
Ni2—N2	2.084 (4)	C9—C11	1.550 (7)
Ni2—N1	2.098 (4)	O5—C20	1.253 (6)
Ni2—O3	2.147 (3)	O5—Ni2ⁱ	2.064 (4)
O1—C1	1.332 (6)	N3—C21	1.319 (7)
O3—C21	1.221 (6)	N3—C22	1.440 (6)
O2—C19	1.321 (5)	N3—C23	1.447 (7)
N2—C12	1.469 (7)	C21—H21	0.892 (19)
N2—C13	1.485 (6)	C22—H22A	0.96
N2—H2N	0.892 (19)	C22—H22B	0.96
N1—C8	1.470 (7)	C22—H22C	0.96
N1—C7	1.492 (7)	C13—H13B	1.06 (4)
N1—H1N	0.890 (19)	C13—H13A	0.964 (19)
O4—C20	1.235 (6)	C10—H10A	0.96
C12—C9	1.523 (8)	C10—H10B	0.96
C12—H12B	0.93 (5)	C10—H10C	0.96
C12—H12A	1.03 (5)	C11—H11A	0.96
C7—C6	1.480 (8)	C11—H11B	0.96
C7—H7A	0.98 (5)	C11—H11C	0.96
C7—H7B	1.00 (5)	C3—C4	1.357 (8)
C1—C2	1.398 (7)	C3—H3	0.93
C1—C6	1.415 (7)	C8—H8A	1.01 (4)
C5—C4	1.370 (8)	C8—H8B	0.937 (19)
C5—C6	1.402 (8)	C16—H16	0.93
C5—H5	0.93	C4—H4	0.93
C2—C3	1.404 (7)	C23—H23B	0.957 (7)
C2—H2	0.93	C23—H23C	1.014 (8)
C18—C17	1.382 (7)	C23—H23A	0.996 (7)
C18—C19	1.406 (7)	C20—H20	0.886 (19)

O1ⁱ—Ni1—O1	180.00 (19)	C17—C18—H18	119.7
O1ⁱ—Ni1—O2	99.66 (12)	C19—C18—H18	119.7
O1—Ni1—O2	80.34 (12)	C16—C15—C14	121.1 (5)
O1ⁱ—Ni1—O2ⁱ	80.34 (12)	C16—C15—H15	119.5
O1—Ni1—O2ⁱ	99.66 (12)	C14—C15—H15	119.5
O2—Ni1—O2ⁱ	180.00 (17)	C15—C14—C19	120.4 (5)
O1ⁱ—Ni1—O4	84.56 (13)	C15—C14—C13	120.1 (5)
O1—Ni1—O4	95.44 (13)	C19—C14—C13	119.5 (5)
O2—Ni1—O4	93.19 (13)	C16—C17—C18	121.2 (6)
O2ⁱ—Ni1—O4	86.81 (13)	C16—C17—H17	119.4
O1ⁱ—Ni1—O4ⁱ	95.44 (13)	C18—C17—H17	119.4
O1—Ni1—O4ⁱ	84.56 (13)	O2—C19—C18	123.0 (5)
O2—Ni1—O4ⁱ	86.81 (13)	O2—C19—C14	119.8 (5)
O2ⁱ—Ni1—O4ⁱ	93.19 (13)	C18—C19—C14	117.2 (5)
O4—Ni1—O4ⁱ	180.0 (2)	C12—C9—C10	110.4 (5)
O1—Ni2—O2	81.85 (12)	C12—C9—C8	112.1 (5)
O1—Ni2—O5ⁱ	90.88 (14)	C10—C9—C8	112.4 (5)
O2—Ni2—O5ⁱ	93.16 (14)	C12—C9—C11	105.8 (5)
O1—Ni2—N2	173.93 (15)	C10—C9—C11	109.3 (5)
O2—Ni2—N2	92.58 (14)	C8—C9—C11	106.6 (5)
O5ⁱ—Ni2—N2	91.84 (16)	C20—O5—Ni2ⁱ	122.2 (4)
O1—Ni2—N1	92.84 (16)	C21—N3—C22	119.8 (5)
O2—Ni2—N1	173.67 (17)	C21—N3—C23	121.7 (5)
O5ⁱ—Ni2—N1	90.35 (18)	C22—N3—C23	117.8 (5)
N2—Ni2—N1	92.58 (17)	O3—C21—N3	126.0 (6)
O1—Ni2—O3	91.51 (13)	O3—C21—H21	122 (3)
O2—Ni2—O3	93.54 (13)	N3—C21—H21	112 (3)
O5ⁱ—Ni2—O3	173.15 (14)	N3—C22—H22A	109.5
N2—Ni2—O3	86.41 (16)	N3—C22—H22B	109.5
N1—Ni2—O3	83.12 (17)	H22A—C22—H22B	109.5
C1—O1—Ni2	120.3 (3)	N3—C22—H22C	109.5
C1—O1—Ni1	135.4 (3)	H22A—C22—H22C	109.5
Ni2—O1—Ni1	97.26 (13)	H22B—C22—H22C	109.5
C21—O3—Ni2	119.6 (4)	N2—C13—C14	113.5 (4)
C19—O2—Ni2	120.4 (3)	N2—C13—H13B	111 (2)
C19—O2—Ni1	136.8 (3)	C14—C13—H13B	109 (2)
Ni2—O2—Ni1	96.77 (13)	N2—C13—H13A	104 (3)
C12—N2—C13	111.1 (4)	C14—C13—H13A	108 (3)
C12—N2—Ni2	114.2 (3)	H13B—C13—H13A	112 (4)
C13—N2—Ni2	110.1 (3)	C9—C10—H10A	109.5
C12—N2—H2N	109 (3)	C9—C10—H10B	109.5
C13—N2—H2N	112 (3)	H10A—C10—H10B	109.5
Ni2—N2—H2N	100 (3)	C9—C10—H10C	109.5
C8—N1—C7	111.2 (5)	H10A—C10—H10C	109.5
C8—N1—Ni2	114.5 (4)	H10B—C10—H10C	109.5
C7—N1—Ni2	109.7 (3)	C9—C11—H11A	109.5
C8—N1—H1N	110 (4)	C9—C11—H11B	109.5
C7—N1—H1N	113 (4)	H11A—C11—H11B	109.5
Ni2—N1—H1N	98 (4)	C9—C11—H11C	109.5
C20—O4—Ni1	128.8 (4)	H11A—C11—H11C	109.5
N2—C12—C9	116.1 (5)	H11B—C11—H11C	109.5
N2—C12—H12B	111 (3)	C4—C3—C2	122.7 (6)
C9—C12—H12B	104 (3)	C4—C3—H3	118.6
N2—C12—H12A	108 (3)	C2—C3—H3	118.6
C9—C12—H12A	105 (3)	N1—C8—C9	114.8 (5)
H12B—C12—H12A	111 (4)	N1—C8—H8A	110 (3)
C6—C7—N1	114.5 (5)	C9—C8—H8A	104 (3)
C6—C7—H7A	113 (3)	N1—C8—H8B	108 (3)
N1—C7—H7A	100 (3)	C9—C8—H8B	104 (3)
C6—C7—H7B	114 (3)	H8A—C8—H8B	117 (4)
N1—C7—H7B	107 (3)	C15—C16—C17	119.4 (5)
H7A—C7—H7B	108 (4)	C15—C16—H16	120.3
O1—C1—C2	121.7 (5)	C17—C16—H16	120.3
O1—C1—C6	119.6 (5)	C3—C4—C5	118.2 (6)
C2—C1—C6	118.7 (5)	C3—C4—H4	120.9
C4—C5—C6	122.3 (6)	C5—C4—H4	120.9
C4—C5—H5	118.8	N3—C23—H23B	118.9 (7)
C6—C5—H5	118.8	N3—C23—H23C	105.7 (6)
C1—C2—C3	119.1 (6)	H23B—C23—H23C	102.5 (6)
C1—C2—H2	120.4	N3—C23—H23A	110.0 (6)
C3—C2—H2	120.4	H23B—C23—H23A	107.9 (7)
C5—C6—C1	118.9 (6)	H23C—C23—H23A	111.6 (8)
C5—C6—C7	121.7 (6)	O4—C20—O5	131.0 (6)
C1—C6—C7	119.4 (5)	O4—C20—H20	113 (3)
C17—C18—C19	120.6 (5)	O5—C20—H20	116 (3)

O2—Ni2—O1—C1	−140.1 (4)	Ni1—O1—C1—C2	−10.3 (7)
O5ⁱ—Ni2—O1—C1	126.8 (4)	Ni2—O1—C1—C6	−45.5 (6)
N1—Ni2—O1—C1	36.4 (4)	Ni1—O1—C1—C6	171.2 (3)
O3—Ni2—O1—C1	−46.8 (4)	O1—C1—C2—C3	−176.5 (5)
O2—Ni1—O1—C1	133.9 (4)	C6—C1—C2—C3	2.1 (8)
O2ⁱ—Ni1—O1—C1	−46.1 (4)	C4—C5—C6—C1	−0.4 (9)
O4—Ni1—O1—C1	41.6 (4)	C4—C5—C6—C7	−178.3 (6)
O4ⁱ—Ni1—O1—C1	−138.4 (4)	O1—C1—C6—C5	177.3 (5)
O1—Ni2—O3—C21	−39.4 (4)	C2—C1—C6—C5	−1.2 (8)
O2—Ni2—O3—C21	42.5 (4)	O1—C1—C6—C7	−4.7 (7)
N2—Ni2—O3—C21	134.9 (4)	C2—C1—C6—C7	176.8 (5)
N1—Ni2—O3—C21	−132.1 (4)	N1—C7—C6—C5	−117.1 (6)
O1—Ni2—O2—C19	142.4 (4)	N1—C7—C6—C1	65.0 (7)
O5ⁱ—Ni2—O2—C19	−127.1 (4)	C16—C15—C14—C19	−1.4 (8)
N2—Ni2—O2—C19	−35.1 (4)	C16—C15—C14—C13	177.4 (5)
O3—Ni2—O2—C19	51.4 (4)	C19—C18—C17—C16	2.4 (9)
O1ⁱ—Ni1—O2—C19	43.8 (4)	Ni2—O2—C19—C18	−134.9 (4)
O1—Ni1—O2—C19	−136.2 (4)	Ni1—O2—C19—C18	10.8 (7)
O4—Ni1—O2—C19	−41.2 (4)	Ni2—O2—C19—C14	44.6 (6)
O4ⁱ—Ni1—O2—C19	138.8 (4)	Ni1—O2—C19—C14	−169.6 (3)
O1ⁱ—Ni1—O2—Ni2	−165.45 (13)	C17—C18—C19—O2	175.7 (5)
O1—Ni1—O2—Ni2	14.55 (13)	C17—C18—C19—C14	−3.9 (8)
O4—Ni1—O2—Ni2	109.53 (14)	C15—C14—C19—O2	−176.2 (4)
O4ⁱ—Ni1—O2—Ni2	−70.47 (14)	C13—C14—C19—O2	5.0 (7)
O2—Ni2—N2—C12	−141.5 (4)	C15—C14—C19—C18	3.4 (7)
O5ⁱ—Ni2—N2—C12	−48.3 (4)	C13—C14—C19—C18	−175.4 (5)
N1—Ni2—N2—C12	42.1 (4)	N2—C12—C9—C10	−58.2 (7)
O3—Ni2—N2—C12	125.1 (4)	N2—C12—C9—C8	67.9 (7)
O2—Ni2—N2—C13	−15.8 (4)	N2—C12—C9—C11	−176.3 (5)
O5ⁱ—Ni2—N2—C13	77.5 (4)	Ni2—O3—C21—N3	141.5 (5)
N1—Ni2—N2—C13	167.9 (4)	C22—N3—C21—O3	−5.4 (9)
O3—Ni2—N2—C13	−109.2 (4)	C23—N3—C21—O3	−175.5 (6)
O1—Ni2—N1—C8	139.8 (4)	C12—N2—C13—C14	−171.7 (5)
O5ⁱ—Ni2—N1—C8	48.9 (4)	Ni2—N2—C13—C14	60.8 (5)
N2—Ni2—N1—C8	−42.9 (4)	C15—C14—C13—N2	115.8 (5)
O3—Ni2—N1—C8	−129.0 (4)	C19—C14—C13—N2	−65.4 (6)
O1—Ni2—N1—C7	14.0 (4)	C1—C2—C3—C4	−1.4 (9)
O5ⁱ—Ni2—N1—C7	−76.9 (4)	C7—N1—C8—C9	−174.9 (5)
N2—Ni2—N1—C7	−168.7 (4)	Ni2—N1—C8—C9	60.1 (6)
O3—Ni2—N1—C7	105.2 (4)	C12—C9—C8—N1	−67.7 (7)
O1ⁱ—Ni1—O4—C20	37.4 (5)	C10—C9—C8—N1	57.3 (7)
O1—Ni1—O4—C20	−142.6 (5)	C11—C9—C8—N1	177.0 (5)
O2—Ni1—O4—C20	136.8 (5)	C14—C15—C16—C17	−0.2 (9)
O2ⁱ—Ni1—O4—C20	−43.2 (5)	C18—C17—C16—C15	−0.2 (9)
C13—N2—C12—C9	175.0 (5)	C2—C3—C4—C5	−0.1 (10)
Ni2—N2—C12—C9	−59.7 (6)	C6—C5—C4—C3	1.1 (10)
C8—N1—C7—C6	172.7 (5)	Ni1—O4—C20—O5	7.0 (10)
Ni2—N1—C7—C6	−59.6 (6)	Ni2ⁱ—O5—C20—O4	−6.5 (9)
Ni2—O1—C1—C2	133.0 (4)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4	0.93	2.52	3.242 (7)	135
C8—H8A···O5ⁱ	1.01 (5)	2.56 (5)	3.133 (6)	116 (3)
C12—H12A···O5ⁱ	1.04 (6)	2.56 (5)	3.156 (8)	116 (4)
C18—H18···O4	0.93	2.52	3.228 (6)	133
C21—H21···O4	0.89 (2)	2.59 (3)	3.353 (7)	144 (4)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni₃(C₁₉H₂₄N₂O₂)₂(CHO₂)₂(C₃H₇NO)₂]
M_r	1037.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.289 (2), 14.054 (5), 17.005 (4)
β (°)	103.433 (19)
V (Å³)	2391.7 (11)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.2 × 0.2 × 0.1

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.720, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	5007, 4740, 2200
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.150, 1.03
No. of reflections	4740
No. of parameters	343
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.49

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4	0.93	2.52	3.242 (7)	135
C8—H8A···O5ⁱ	1.01 (5)	2.56 (5)	3.133 (6)	116 (3)
C12—H12A···O5ⁱ	1.04 (6)	2.56 (5)	3.156 (8)	116 (4)
C18—H18···O4	0.93	2.52	3.228 (6)	133
C21—H21···O4	0.89 (2)	2.59 (3)	3.353 (7)	144 (4)

Symmetry code: (i) −x, −y, −z.

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		Medline
		CIF
		SGML
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		Plain Text

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Bis[μ2-2,2′-dimethyl-N,N′-bis­(2-oxido­benz­yl)propane-1,3-diamine]-1κ4O,N,N′,O′:2κ2O,O′;2κ2O,O′:3κ4O,N,N′,O′-bis­(N,N′-dimethyl­formamide)-1κO,3κO-di-μ2-formato-1:2κ2O:O′;2:3κ2O:O′-trinickel(II)

Supporting information

Key indicators

checkCIF/PLATON results

Bis[μ₂-2,2′-dimethyl-N,N′-bis(2-oxidobenzyl)propane-1,3-diamine]-1κ⁴O,N,N′,O′:2κ²O,O′;2κ²O,O′:3κ⁴O,N,N′,O′-bis(N,N′-dimethylformamide)-1κO,3κO-di-μ₂-formato-1:2κ²O:O′;2:3κ²O:O′-trinickel(II)