The coordination polyhedra of the nickel(II) ions of the title compound in the complex cation and the anion, viz., trans-NiN4O2 and trans-NiO4N2, are distorted octahedra. In the crystal, the donor groups of the tetraamine and the coordinated water molecules and the carboxylate groups of the pyridine-2,6-dicarboxylate anions are involved in numerous N—H⋯O and O—H⋯O hydrogen bonds, thereby forming sheets of ions lying parallel to the (001) plane.
Keywords: crystal structure; cyclam; nickel; pyridine-2,6-dicarboxylate; hydrogen bonds
Abstract
The asymmetric unit of the title compound, trans-diaqua(1,4,8,11-tetraazaundecane-κ4 N 1,N 4,N 8,N 11)nickel(II) bis(pyridine-2,6-dicarboxylato-κ3 O 2,N,O 6)nickel(II) {[Ni(L)(H2O)2][Ni(pdc)2] where L = 1,4,8,11-tetraazaundecane (C7H20N4) and pdc = the dianion of pyridine-2,6-dicarboxylic acid (C7H3NO4 2−)} consists of an [Ni(L)(H2O)2]2+ complex cation and a [Ni(pdc)2]2– anion. The metal ion in the cation is coordinated by the four N atoms of the tetraamine ligand and the mutually trans O atoms of the water molecules in a tetragonally elongated octahedral geometry with the average equatorial Ni—N bond length slightly shorter than the average axial Ni—O bond [2.087 (4) versus 2.128 (4) Å]. The ligand L adopts its energetically favored conformation with five-membered and six-membered chelate rings in gauche and chair conformations, respectively. In the complex anion, the NiII ion is coordinated by the two tridentate pdc2– ligands via their carboxylate and nitrogen atom donors in a distorted octahedral trans-NiO4N2 geometry with nearly orthogonal orientation of the planes defining the carboxylate rings and the average Ni—N bond length [1.965 (4) Å] shorter than the average Ni—O bond distance [2.113 (7) Å]. In the crystal, the NH donor groups of the tetraamine, the carboxylic groups of the pdc2– anion and the coordinated water molecules are involved in numerous N—H⋯O and O—H⋯O hydrogen bonds, leading to electroneutral sheets oriented parallel to the (001) plane.
Chemical context
Crystalline coordination polymers possessing permanent porosity (metal–organic frameworks, MOFs) are of enormous current interest because of their potential for applications in different areas including gas storage, separation, catalysis, etc. (MacGillivray & Lukehart, 2014 ▸; Kaskel, 2016 ▸). Nickel(II) complexes of the 14-membered macrocyclic tetraamine ligands, in particular of cyclam and its C-alkylated derivatives (cyclam = 1,4,8,11-tetraazacyclotetradecane, C10H24N4), are widely used as metal-containing building units for the construction of MOFs (Lampeka & Tsymbal, 2004 ▸; Suh & Moon, 2007 ▸; Suh et al., 2012 ▸; Stackhouse & Ma, 2018 ▸; Lee & Moon, 2018 ▸). At the same time, nickel(II) complexes of 1,4,8,11-tetraazaundecane (C7H20N4; L) – the closest open-chain analogue of cyclam – are rarely utilized for the construction of MOFs and only a few examples of coordination polymers formed by the [Ni(L)]2+ cation with azide (Escuer et al., 1993 ▸), cyanide (Koo et al., 2003 ▸), and cyanometalate (Koo et al., 2003 ▸; Shek et al., 2005 ▸; Talukder et al., 2012 ▸; Ni et al., 2014 ▸) bridging anions have been characterized by single-crystal X-ray diffraction.
Multidentate aromatic carboxylates are known as the most common linkers in MOFs (Rao et al., 2004 ▸). Although the bridging properties of one of the simplest representative of this class of compounds, 1,3-benzenedicarboxylate, with macrocyclic nickel(II) cations are well studied (see, for example, Tsymbal et al., 2021 ▸), coordination polymers based on its structural analogue, pyridine-2,6-dicarboxylate (C7H3NO4 2–; pdc2–), are confined to a sole example (Choi et al., 2003 ▸). Interestingly, an attempt to prepare a coordination polymer containing the [Ni(cyclam)]2+ cation with pdc2– led to the ionic product [Ni(cyclam)(H2O)2][Ni(pdc)2]·2.5H2O due to sequestering of the metal ion from the cavity of the macrocycle by this chelating ligand (Park et al., 2007 ▸).
As part of our research on MOFs formed by nickel(II) tetraaza cations and aromatic carboxylates, we report here the synthesis and crystal structure of the product of the reaction of [Ni(L)]2+ with pdc2–, namely [trans-diaqua(1,4,8,11-tetraazaundecane-k 4 N 1 N 4 N 8 N 11)nickel(II)][bis(pyridine-2,6-dicarboxylato-κ 3 N,O,O)nickel(II)], [Ni(L)(H2O)2][Ni(pdc)2], I. Similar to the reaction of pyridine-2,6-dicarboxylate with the [Ni(cyclam)]2+ cation, the formation of the title compound is explained by the sequestering of the metal ion from the starting cation with the formation of the [Ni(pdc)2]2– anion. Additionally, to the best of our knowledge, the structure of the [trans-diaqua(1,4,8,11-tetraazaundecane)nickel(II)] moiety has not previously been reported in the literature.
Structural commentary
The molecular structure of the title compound I is shown in Fig. 1 ▸. Atom Ni1 is coordinated by the two tridentate pdc2– ligands via their carboxylate and nitrogen donors, resulting in the formation of the [Ni(pdc)2]2– divalent anion, which is charge-balanced by the [Ni(L)(H2O)2]2+ divalent cation formed by atom Ni2.
Figure 1.
View of the molecular structure of I, showing the partial atom-labeling scheme, with displacement ellipsoids drawn at the 40% probability level. C-bound H atoms are omitted for clarity. Hydrogen-bonding interactions are shown as dotted lines.
The coordination polyhedron of Ni1II in the complex anion ion can be described as a tetragonally compressed trans-NiO4N2 octahedron with the Ni—N bond lengths [average value 1.965 (4) Å] shorter than the Ni—O ones [average value 2.113 (7) Å] (Table 1 ▸). Another source of distortion is the alternating displacement (by ca 0.43 Å) of the coordinated oxygen atoms of deprotonated carboxylic groups from the mean equatorial plane formed by the four oxygen atoms. The values of the bite angles in the five-membered chelate rings in the complex anion are very similar (Table 1 ▸). The pdc2– carboxylate rings are oriented nearly orthogonally with an angle of 81.5 (3)° between their mean planes.
Table 1. Selected geometric parameters (Å, °).
| Ni1—O1 | 2.099 (2) | Ni2—O1W | 2.131 (2) |
| Ni1—O3 | 2.109 (2) | Ni2—O2W | 2.124 (2) |
| Ni1—O5 | 2.111 (2) | Ni2—N3 | 2.074 (2) |
| Ni1—O7 | 2.1343 (19) | Ni2—N4 | 2.088 (2) |
| Ni1—N1 | 1.961 (2) | Ni2—N5 | 2.095 (2) |
| Ni1—N2 | 1.969 (2) | Ni2—N6 | 2.089 (3) |
| O1—Ni1—O3 | 156.79 (8) | O2W—Ni2—O1W | 174.88 (8) |
| O1—Ni1—O5 | 95.74 (8) | N3—Ni2—O1W | 86.26 (9) |
| O1—Ni1—O7 | 89.96 (8) | N3—Ni2—O2W | 92.25 (9) |
| O3—Ni1—O5 | 89.36 (8) | N3—Ni2—N4 | 84.10 (10) |
| O3—Ni1—O7 | 94.68 (8) | N3—Ni2—N5 | 174.54 (10) |
| O5—Ni1—O7 | 155.62 (7) | N3—Ni2—N6 | 101.01 (10) |
| N1—Ni1—O1 | 78.63 (9) | N4—Ni2—O1W | 87.83 (9) |
| N1—Ni1—O3 | 78.19 (9) | N4—Ni2—O2W | 96.90 (9) |
| N1—Ni1—O5 | 105.53 (9) | N4—Ni2—N5 | 90.45 (10) |
| N1—Ni1—O7 | 98.84 (9) | N4—Ni2—N6 | 172.57 (10) |
| N1—Ni1—N2 | 176.06 (10) | N5—Ni2—O1W | 93.07 (9) |
| N2—Ni1—O1 | 99.61 (9) | N5—Ni2—O2W | 88.86 (9) |
| N2—Ni1—O3 | 103.60 (9) | N6—Ni2—O1W | 87.13 (9) |
| N2—Ni1—O5 | 78.10 (9) | N6—Ni2—O2W | 88.34 (9) |
| N2—Ni1—O7 | 77.58 (9) | N6—Ni2—N5 | 84.36 (10) |
The Ni2II ion in the complex cation is coordinated by the four N atoms of the ligand L and the mutually trans O atoms of the water molecules in a tetragonally elongated trans-NiN4O2 octahedral geometry with the average equatorial Ni—N bond length slightly shorter than the average axial Ni—O bond [2.087 (4) and 2.128 (4) Å, respectively (Table 1 ▸)]. The ligand L in I adopts its energetically favored conformation with the five-membered and six-membered chelate rings in gauche and chair conformations, respectively, which resemble the trans-III configuration usually observed in cyclam complexes (Bosnich et al., 1965 ▸). This conformation is also characteristic of the macrocyclic ligand in [Ni(cyclam)(H2O)2]2+ (Park et al., 2007 ▸), although the bite angles in the five-membered (85.54°) and six-membered (94.46°) chelate rings are correspondingly larger and smaller compared to those in I (Table 1 ▸).
Supramolecular features
The crystals of I are composed of [Ni(L)(H2O)2]2+ complex cations and [Ni(pdc)2]2– anions connected by numerous hydrogen bonds (Table 2 ▸). Each ion is surrounded by four counter-ions (Figs. 2 ▸ and 3 ▸); the cation acts as the hydrogen-bond donor due to the presence of the N—H fragments of amino groups and the O—H groups of coordinated water molecules, while the anion displays proton-acceptor properties because of the availability of the carboxylic groups. These aggregates are further arranged into two-dimensional sheets oriented parallel to the (001) plane (Fig. 4 ▸). There are no hydrogen-bonding contacts between the sheets, and the three-dimensional coherence of the crystal is provided by van der Waals interactions.
Table 2. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N3—H3A⋯O8i | 0.91 | 2.41 | 3.213 (3) | 147 |
| N3—H3B⋯O4ii | 0.91 | 2.11 | 3.015 (3) | 176 |
| N4—H4A⋯O1 | 1.00 | 2.07 | 3.054 (3) | 167 |
| N5—H5A⋯O2 | 1.00 | 2.08 | 3.054 (3) | 163 |
| N6—H6A⋯O3ii | 0.91 | 2.14 | 2.986 (3) | 154 |
| N6—H6B⋯O6iii | 0.91 | 2.07 | 2.943 (3) | 160 |
| O1W—H1WA⋯O1 | 0.86 | 2.56 | 3.088 (3) | 121 |
| O1W—H1WA⋯O2 | 0.86 | 2.00 | 2.795 (3) | 154 |
| O1W—H1WB⋯O3ii | 0.86 | 1.91 | 2.757 (3) | 170 |
| O2W—H2WA⋯O7i | 0.87 | 1.80 | 2.663 (3) | 169 |
| O2W—H2WB⋯O6iii | 0.87 | 1.90 | 2.742 (3) | 160 |
Symmetry codes: (i) x-1, y, z; (ii) -x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}; (iii) -x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}.
Figure 2.
Nearest surroundings of the cation in I formed by hydrogen bonding (dotted lines). [Symmetry codes: (i) x − 1, y, z; (ii) −x + 1, y +
, −z +
; (iii) −x + 2, y +
, −z +
.]
Figure 3.
Nearest surroundings of the anion in I formed by hydrogen bonding (dotted lines). [Symmetry codes: (i) x + 1, y, z; (ii) −x + 2, y −
, −z +
; (iii) −x + 1, y −
, −z +
Figure 4.
Electroneutral sheets of the complex ions in I parallel to the (001) plane. C-bound H atoms are omitted for clarity. C atoms of the cation and anion are shown in purple and green, respectively. Hydrogen bonds are shown as dotted lines.
Database survey
A search of the Cambridge Structural Database (CSD, version 5.42, last update February 2021; Groom et al., 2016 ▸) indicated that no compounds containing the [Ni(L)(H2O)2]2+ cation have been structurally characterized to date, the closest analogue being the complex [Ni(L)(H2O)(Cl)]Cl (refcode UMOFEH; Oblezov et al., 2003 ▸). In general, the geometrical parameters of both cations in these compounds are similar, although the Ni—O bond length in the latter is longer (2.182 Å), probably because of the trans influence of the chloride ligand.
As far as the structures of the cations in the compounds with the same bis(pyridine-2,6-dicarboxylato)-nickel(II) anion are concerned, {[Ni(L)(H2O)2]2+ in I and [Ni(cyclam)(H2O)2]2+ in TICJEV (Park et al., 2007 ▸)}, a higher tetragonal distortion of the coordination polyhedron in the latter case [average Ni—N bond length of 2.068 (6) Å and Ni—O bond length of 2.152 Å] should be mentioned, which can be explained by the stronger cis influence of the macrocyclic ligand compared to the non-cyclic one (Yatsimirskii & Lampeka, 1985 ▸).
Synthesis and crystallization
All chemicals and solvents used in this work were purchased from Sigma–Aldrich and used without further purification. The complex [Ni(L)](ClO4)2 was prepared by mixing equimolar amount of L and nickel perchlorate hexahydrate in ethanol. The title compound I was prepared as follows. A solution of [Ni(L)](ClO4)2 (11 mg, 0.026 mmol) in 1 ml of DMF was added to 0.4 ml of an aqueous solution of Na2(pdc) (2.7 mg, 0.013 mmol). Blue crystals formed in a day, which were filtered off, washed with diethyl ether and dried in air. Yield: 1.3 mg (15.5%). Analysis calculated for C21H30N6Ni2O10: C 39.17, H 4.66, N 13.06%. Found: C 39.04, H 5.0, N 13.21%. Single crystals of I suitable for X-ray diffraction analysis were selected from the sample resulting from the synthesis.
Safety note: Perchlorate salts of metal complexes are potentially explosive and should be handled with care.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. H atoms in I were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 (ring H atoms) or 0.99 Å (aliphatic H atoms), N—H distances of 0.91 (primary amino groups) or 1.00 Å (secondary aminogroups) with U iso(H) values of 1.2U eq of the parent atoms. Water H atoms were positioned geometrically (O—H = 0.71–0.85 Å) and refined as riding with U iso(H) = 1.5U eq(O).
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | [Ni(C7H20N4)(H2O)2][Ni(C7H3NO4)2] |
| M r | 643.93 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 100 |
| a, b, c (Å) | 9.3219 (6), 16.3211 (10), 16.9483 (8) |
| V (Å3) | 2578.6 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 1.53 |
| Crystal size (mm) | 0.25 × 0.2 × 0.2 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (CrysAlis PRO; Rigaku OD, 2019 ▸) |
| T min, T max | 0.705, 0.737 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 36128, 4909, 4668 |
| R int | 0.045 |
| (sin θ/λ)max (Å−1) | 0.610 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.021, 0.050, 1.04 |
| No. of reflections | 4909 |
| No. of parameters | 356 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.49, −0.26 |
| Absolute structure | Flack x determined using 1953 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸) |
| Absolute structure parameter | −0.010 (4) |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989021011178/hb7995sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021011178/hb7995Isup2.hkl
CCDC reference: 2115829
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| [Ni(C7H20N4)(H2O)2][Ni(C7H3NO4)2] | Dx = 1.659 Mg m−3 |
| Mr = 643.93 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, P212121 | Cell parameters from 8341 reflections |
| a = 9.3219 (6) Å | θ = 2.5–25.3° |
| b = 16.3211 (10) Å | µ = 1.53 mm−1 |
| c = 16.9483 (8) Å | T = 100 K |
| V = 2578.6 (3) Å3 | Prism, clear light pink |
| Z = 4 | 0.25 × 0.2 × 0.2 mm |
| F(000) = 1336 |
Data collection
| Bruker APEXII CCD diffractometer | 4668 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.045 |
| φ and ω scans | θmax = 25.7°, θmin = 2.4° |
| Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019) | h = −11→11 |
| Tmin = 0.705, Tmax = 0.737 | k = −19→19 |
| 36128 measured reflections | l = −20→20 |
| 4909 independent reflections |
Refinement
| Refinement on F2 | Hydrogen site location: mixed |
| Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.021 | w = 1/[σ2(Fo2) + (0.0243P)2 + 0.7375P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.050 | (Δ/σ)max = 0.002 |
| S = 1.04 | Δρmax = 0.49 e Å−3 |
| 4909 reflections | Δρmin = −0.26 e Å−3 |
| 356 parameters | Absolute structure: Flack x determined using 1953 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
| 0 restraints | Absolute structure parameter: −0.010 (4) |
| Primary atom site location: dual |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Ni1 | 1.09379 (4) | 0.79146 (2) | 0.79300 (2) | 0.01132 (9) | |
| O1 | 0.9734 (2) | 0.89973 (12) | 0.80207 (12) | 0.0156 (4) | |
| O3 | 1.2374 (2) | 0.69917 (13) | 0.82970 (11) | 0.0150 (4) | |
| O2 | 0.9525 (2) | 1.01235 (13) | 0.87640 (12) | 0.0190 (5) | |
| O4 | 1.3661 (3) | 0.65997 (13) | 0.93534 (13) | 0.0250 (5) | |
| O5 | 0.9208 (2) | 0.71131 (13) | 0.81555 (11) | 0.0178 (4) | |
| O7 | 1.2475 (2) | 0.85377 (12) | 0.72153 (10) | 0.0151 (4) | |
| O6 | 0.7669 (2) | 0.62760 (13) | 0.75366 (12) | 0.0208 (5) | |
| O8 | 1.2894 (2) | 0.88805 (13) | 0.59530 (12) | 0.0197 (5) | |
| N1 | 1.1543 (3) | 0.83219 (15) | 0.89664 (13) | 0.0117 (5) | |
| N2 | 1.0390 (3) | 0.75735 (15) | 0.68573 (13) | 0.0124 (5) | |
| C1 | 1.0034 (3) | 0.94313 (19) | 0.86156 (17) | 0.0147 (6) | |
| C2 | 1.1083 (3) | 0.90574 (17) | 0.91977 (15) | 0.0136 (6) | |
| C3 | 1.1561 (3) | 0.93967 (19) | 0.98988 (17) | 0.0160 (6) | |
| H3 | 1.127255 | 0.993102 | 1.005442 | 0.019* | |
| C4 | 1.2481 (3) | 0.89317 (19) | 1.03707 (17) | 0.0178 (7) | |
| H4 | 1.278944 | 0.913881 | 1.086623 | 0.021* | |
| C5 | 1.2944 (3) | 0.81687 (19) | 1.01178 (16) | 0.0155 (6) | |
| H5 | 1.357733 | 0.785035 | 1.043217 | 0.019* | |
| C6 | 1.2463 (3) | 0.78819 (18) | 0.93978 (16) | 0.0136 (6) | |
| C7 | 1.2889 (3) | 0.70808 (19) | 0.90009 (17) | 0.0154 (6) | |
| C8 | 0.8683 (3) | 0.67716 (17) | 0.75527 (17) | 0.0149 (6) | |
| C9 | 0.9355 (3) | 0.70262 (18) | 0.67704 (17) | 0.0131 (6) | |
| C10 | 0.8957 (4) | 0.67512 (17) | 0.60250 (17) | 0.0166 (6) | |
| H10 | 0.821798 | 0.635587 | 0.596314 | 0.020* | |
| C11 | 0.9667 (3) | 0.7068 (2) | 0.53760 (18) | 0.0194 (7) | |
| H11 | 0.941943 | 0.688728 | 0.486084 | 0.023* | |
| C12 | 1.0745 (3) | 0.76525 (18) | 0.54766 (16) | 0.0164 (6) | |
| H12 | 1.123225 | 0.787779 | 0.503466 | 0.020* | |
| C13 | 1.1087 (3) | 0.78960 (17) | 0.62377 (16) | 0.0132 (6) | |
| C14 | 1.2247 (3) | 0.84969 (18) | 0.64704 (16) | 0.0147 (6) | |
| Ni2 | 0.58765 (4) | 1.01066 (2) | 0.76468 (2) | 0.01201 (9) | |
| O1W | 0.8016 (2) | 1.04716 (13) | 0.73792 (12) | 0.0192 (5) | |
| H1WA | 0.869828 | 1.041746 | 0.771368 | 0.031 (10)* | |
| H1WB | 0.797698 | 1.092906 | 0.712918 | 0.040 (11)* | |
| O2W | 0.3684 (2) | 0.98471 (13) | 0.78767 (12) | 0.0172 (4) | |
| H2WA | 0.325706 | 0.939783 | 0.772223 | 0.042 (12)* | |
| H2WB | 0.308376 | 1.025333 | 0.781113 | 0.069 (16)* | |
| N3 | 0.5586 (3) | 1.00016 (16) | 0.64375 (14) | 0.0192 (6) | |
| H3A | 0.465077 | 0.989548 | 0.632344 | 0.023* | |
| H3B | 0.584859 | 1.047317 | 0.618999 | 0.023* | |
| N4 | 0.6569 (3) | 0.88925 (15) | 0.75663 (15) | 0.0174 (5) | |
| H4A | 0.763467 | 0.890194 | 0.763131 | 0.021* | |
| N5 | 0.6255 (3) | 1.01005 (15) | 0.88651 (13) | 0.0163 (5) | |
| H5A | 0.731507 | 1.013124 | 0.894920 | 0.020* | |
| N6 | 0.5419 (3) | 1.13467 (15) | 0.78184 (14) | 0.0170 (6) | |
| H6A | 0.586732 | 1.165700 | 0.744666 | 0.020* | |
| H6B | 0.445736 | 1.143679 | 0.778488 | 0.020* | |
| C15 | 0.6505 (4) | 0.9317 (2) | 0.61828 (18) | 0.0236 (7) | |
| H15A | 0.752369 | 0.948818 | 0.618268 | 0.028* | |
| H15B | 0.624339 | 0.914509 | 0.564135 | 0.028* | |
| C16 | 0.6286 (4) | 0.8613 (2) | 0.67532 (19) | 0.0226 (8) | |
| H16A | 0.528893 | 0.840840 | 0.671222 | 0.027* | |
| H16B | 0.694390 | 0.815805 | 0.661796 | 0.027* | |
| C17 | 0.6005 (4) | 0.83218 (18) | 0.81722 (18) | 0.0210 (7) | |
| H17A | 0.639786 | 0.776760 | 0.807346 | 0.025* | |
| H17B | 0.494866 | 0.829025 | 0.812244 | 0.025* | |
| C18 | 0.6383 (4) | 0.8580 (2) | 0.90014 (19) | 0.0234 (8) | |
| H18A | 0.743906 | 0.863351 | 0.903632 | 0.028* | |
| H18B | 0.609403 | 0.813510 | 0.936547 | 0.028* | |
| C19 | 0.5716 (4) | 0.93725 (19) | 0.92903 (18) | 0.0230 (7) | |
| H19A | 0.466236 | 0.934035 | 0.922537 | 0.028* | |
| H19B | 0.592126 | 0.943637 | 0.986010 | 0.028* | |
| C20 | 0.5617 (4) | 1.0860 (2) | 0.91737 (18) | 0.0216 (8) | |
| H20A | 0.601711 | 1.098266 | 0.970176 | 0.026* | |
| H20B | 0.456571 | 1.079348 | 0.922625 | 0.026* | |
| C21 | 0.5947 (4) | 1.15564 (18) | 0.86117 (17) | 0.0207 (7) | |
| H21A | 0.547856 | 1.206507 | 0.879817 | 0.025* | |
| H21B | 0.699559 | 1.165229 | 0.859354 | 0.025* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.01194 (18) | 0.01160 (18) | 0.01043 (16) | −0.00100 (17) | −0.00079 (17) | −0.00127 (13) |
| O1 | 0.0139 (10) | 0.0152 (11) | 0.0177 (10) | 0.0013 (9) | −0.0033 (8) | −0.0023 (9) |
| O3 | 0.0179 (11) | 0.0130 (11) | 0.0142 (10) | 0.0014 (9) | −0.0025 (9) | −0.0030 (8) |
| O2 | 0.0168 (11) | 0.0133 (11) | 0.0270 (11) | 0.0034 (9) | −0.0032 (8) | −0.0013 (9) |
| O4 | 0.0324 (14) | 0.0204 (13) | 0.0222 (11) | 0.0110 (10) | −0.0066 (10) | −0.0003 (9) |
| O5 | 0.0170 (11) | 0.0199 (11) | 0.0164 (10) | −0.0050 (11) | 0.0015 (9) | −0.0006 (8) |
| O7 | 0.0161 (11) | 0.0165 (11) | 0.0126 (11) | −0.0039 (9) | −0.0008 (8) | −0.0009 (8) |
| O6 | 0.0182 (12) | 0.0174 (11) | 0.0267 (12) | −0.0069 (10) | 0.0006 (9) | −0.0020 (9) |
| O8 | 0.0209 (12) | 0.0198 (12) | 0.0185 (11) | −0.0028 (10) | 0.0058 (9) | 0.0036 (9) |
| N1 | 0.0110 (12) | 0.0126 (13) | 0.0115 (12) | −0.0015 (10) | 0.0003 (10) | −0.0001 (10) |
| N2 | 0.0113 (12) | 0.0116 (13) | 0.0141 (12) | 0.0025 (10) | −0.0014 (9) | −0.0013 (10) |
| C1 | 0.0084 (16) | 0.0155 (17) | 0.0203 (15) | 0.0004 (13) | 0.0032 (12) | 0.0010 (12) |
| C2 | 0.0135 (16) | 0.0124 (15) | 0.0148 (13) | −0.0028 (13) | 0.0030 (12) | 0.0004 (11) |
| C3 | 0.0179 (16) | 0.0148 (17) | 0.0153 (14) | −0.0031 (13) | 0.0037 (12) | −0.0031 (12) |
| C4 | 0.0216 (18) | 0.0201 (17) | 0.0117 (13) | −0.0037 (14) | 0.0006 (12) | −0.0027 (12) |
| C5 | 0.0159 (16) | 0.0180 (17) | 0.0127 (14) | −0.0021 (13) | −0.0009 (12) | 0.0028 (12) |
| C6 | 0.0123 (15) | 0.0138 (15) | 0.0148 (14) | −0.0024 (13) | 0.0020 (11) | 0.0025 (11) |
| C7 | 0.0150 (15) | 0.0151 (16) | 0.0160 (14) | 0.0002 (13) | 0.0029 (12) | 0.0002 (12) |
| C8 | 0.0126 (16) | 0.0118 (15) | 0.0204 (16) | 0.0002 (12) | 0.0017 (12) | 0.0001 (12) |
| C9 | 0.0103 (15) | 0.0100 (14) | 0.0190 (14) | 0.0026 (12) | −0.0021 (11) | −0.0010 (11) |
| C10 | 0.0160 (16) | 0.0127 (15) | 0.0212 (15) | 0.0007 (14) | −0.0074 (14) | −0.0018 (11) |
| C11 | 0.0226 (17) | 0.0200 (17) | 0.0154 (14) | 0.0049 (14) | −0.0060 (12) | −0.0026 (13) |
| C12 | 0.0194 (17) | 0.0177 (16) | 0.0122 (13) | 0.0032 (14) | −0.0009 (12) | 0.0019 (11) |
| C13 | 0.0132 (15) | 0.0121 (14) | 0.0142 (13) | 0.0041 (13) | 0.0001 (12) | 0.0012 (11) |
| C14 | 0.0110 (15) | 0.0142 (16) | 0.0191 (15) | 0.0044 (13) | 0.0012 (12) | −0.0013 (12) |
| Ni2 | 0.01145 (18) | 0.01053 (18) | 0.01407 (17) | −0.00027 (16) | −0.00135 (15) | 0.00039 (13) |
| O1W | 0.0169 (12) | 0.0177 (12) | 0.0231 (11) | −0.0015 (9) | −0.0018 (9) | 0.0056 (9) |
| O2W | 0.0143 (10) | 0.0127 (11) | 0.0247 (11) | 0.0001 (9) | −0.0021 (8) | 0.0009 (9) |
| N3 | 0.0191 (15) | 0.0190 (15) | 0.0195 (13) | −0.0019 (12) | −0.0024 (10) | 0.0010 (11) |
| N4 | 0.0147 (13) | 0.0142 (14) | 0.0232 (13) | 0.0001 (11) | −0.0017 (10) | −0.0007 (11) |
| N5 | 0.0148 (14) | 0.0166 (13) | 0.0174 (12) | −0.0005 (11) | −0.0015 (10) | 0.0031 (10) |
| N6 | 0.0156 (13) | 0.0147 (13) | 0.0207 (14) | 0.0001 (10) | 0.0007 (10) | 0.0028 (11) |
| C15 | 0.0248 (18) | 0.0260 (19) | 0.0201 (16) | 0.0000 (15) | −0.0007 (13) | −0.0062 (14) |
| C16 | 0.0199 (19) | 0.0188 (18) | 0.0292 (17) | 0.0016 (14) | −0.0029 (13) | −0.0074 (14) |
| C17 | 0.0163 (16) | 0.0118 (15) | 0.0350 (17) | 0.0008 (14) | 0.0018 (15) | 0.0018 (12) |
| C18 | 0.0204 (18) | 0.0197 (18) | 0.0301 (18) | −0.0005 (14) | 0.0004 (14) | 0.0097 (14) |
| C19 | 0.0228 (19) | 0.0250 (19) | 0.0213 (15) | −0.0020 (15) | 0.0025 (14) | 0.0091 (13) |
| C20 | 0.025 (2) | 0.0221 (18) | 0.0179 (15) | 0.0019 (14) | 0.0001 (13) | −0.0043 (13) |
| C21 | 0.0234 (17) | 0.0136 (15) | 0.0252 (16) | −0.0018 (16) | 0.0012 (16) | −0.0046 (12) |
Geometric parameters (Å, º)
| Ni1—O1 | 2.099 (2) | Ni2—N3 | 2.074 (2) |
| Ni1—O3 | 2.109 (2) | Ni2—N4 | 2.088 (2) |
| Ni1—O5 | 2.111 (2) | Ni2—N5 | 2.095 (2) |
| Ni1—O7 | 2.1343 (19) | Ni2—N6 | 2.089 (3) |
| Ni1—N1 | 1.961 (2) | O1W—H1WA | 0.8563 |
| Ni1—N2 | 1.969 (2) | O1W—H1WB | 0.8593 |
| O1—C1 | 1.264 (4) | O2W—H2WA | 0.8743 |
| O3—C7 | 1.294 (3) | O2W—H2WB | 0.8744 |
| O2—C1 | 1.251 (4) | N3—H3A | 0.9100 |
| O4—C7 | 1.221 (4) | N3—H3B | 0.9100 |
| O5—C8 | 1.262 (3) | N3—C15 | 1.473 (4) |
| O7—C14 | 1.282 (3) | N4—H4A | 1.0000 |
| O6—C8 | 1.245 (3) | N4—C16 | 1.475 (4) |
| O8—C14 | 1.235 (4) | N4—C17 | 1.483 (4) |
| N1—C2 | 1.334 (4) | N5—H5A | 1.0000 |
| N1—C6 | 1.336 (4) | N5—C19 | 1.477 (4) |
| N2—C9 | 1.323 (4) | N5—C20 | 1.471 (4) |
| N2—C13 | 1.343 (4) | N6—H6A | 0.9100 |
| C1—C2 | 1.517 (4) | N6—H6B | 0.9100 |
| C2—C3 | 1.385 (4) | N6—C21 | 1.472 (4) |
| C3—H3 | 0.9500 | C15—H15A | 0.9900 |
| C3—C4 | 1.396 (4) | C15—H15B | 0.9900 |
| C4—H4 | 0.9500 | C15—C16 | 1.515 (5) |
| C4—C5 | 1.386 (4) | C16—H16A | 0.9900 |
| C5—H5 | 0.9500 | C16—H16B | 0.9900 |
| C5—C6 | 1.382 (4) | C17—H17A | 0.9900 |
| C6—C7 | 1.523 (4) | C17—H17B | 0.9900 |
| C8—C9 | 1.524 (4) | C17—C18 | 1.509 (4) |
| C9—C10 | 1.391 (4) | C18—H18A | 0.9900 |
| C10—H10 | 0.9500 | C18—H18B | 0.9900 |
| C10—C11 | 1.384 (4) | C18—C19 | 1.517 (5) |
| C11—H11 | 0.9500 | C19—H19A | 0.9900 |
| C11—C12 | 1.396 (5) | C19—H19B | 0.9900 |
| C12—H12 | 0.9500 | C20—H20A | 0.9900 |
| C12—C13 | 1.387 (4) | C20—H20B | 0.9900 |
| C13—C14 | 1.512 (4) | C20—C21 | 1.515 (4) |
| Ni2—O1W | 2.131 (2) | C21—H21A | 0.9900 |
| Ni2—O2W | 2.124 (2) | C21—H21B | 0.9900 |
| O1—Ni1—O3 | 156.79 (8) | N5—Ni2—O1W | 93.07 (9) |
| O1—Ni1—O5 | 95.74 (8) | N5—Ni2—O2W | 88.86 (9) |
| O1—Ni1—O7 | 89.96 (8) | N6—Ni2—O1W | 87.13 (9) |
| O3—Ni1—O5 | 89.36 (8) | N6—Ni2—O2W | 88.34 (9) |
| O3—Ni1—O7 | 94.68 (8) | N6—Ni2—N5 | 84.36 (10) |
| O5—Ni1—O7 | 155.62 (7) | Ni2—O1W—H1WA | 121.7 |
| N1—Ni1—O1 | 78.63 (9) | Ni2—O1W—H1WB | 107.9 |
| N1—Ni1—O3 | 78.19 (9) | H1WA—O1W—H1WB | 116.6 |
| N1—Ni1—O5 | 105.53 (9) | Ni2—O2W—H2WA | 123.4 |
| N1—Ni1—O7 | 98.84 (9) | Ni2—O2W—H2WB | 116.2 |
| N1—Ni1—N2 | 176.06 (10) | H2WA—O2W—H2WB | 107.9 |
| N2—Ni1—O1 | 99.61 (9) | Ni2—N3—H3A | 110.5 |
| N2—Ni1—O3 | 103.60 (9) | Ni2—N3—H3B | 110.5 |
| N2—Ni1—O5 | 78.10 (9) | H3A—N3—H3B | 108.7 |
| N2—Ni1—O7 | 77.58 (9) | C15—N3—Ni2 | 106.06 (18) |
| C1—O1—Ni1 | 114.33 (19) | C15—N3—H3A | 110.5 |
| C7—O3—Ni1 | 115.29 (18) | C15—N3—H3B | 110.5 |
| C8—O5—Ni1 | 115.02 (18) | Ni2—N4—H4A | 106.6 |
| C14—O7—Ni1 | 115.00 (19) | C16—N4—Ni2 | 107.41 (19) |
| C2—N1—Ni1 | 118.40 (19) | C16—N4—H4A | 106.6 |
| C2—N1—C6 | 122.0 (3) | C16—N4—C17 | 112.9 (2) |
| C6—N1—Ni1 | 119.5 (2) | C17—N4—Ni2 | 116.20 (19) |
| C9—N2—Ni1 | 118.88 (19) | C17—N4—H4A | 106.6 |
| C9—N2—C13 | 122.1 (2) | Ni2—N5—H5A | 107.9 |
| C13—N2—Ni1 | 119.07 (19) | C19—N5—Ni2 | 115.30 (19) |
| O1—C1—C2 | 115.9 (3) | C19—N5—H5A | 107.9 |
| O2—C1—O1 | 125.6 (3) | C20—N5—Ni2 | 106.17 (18) |
| O2—C1—C2 | 118.5 (3) | C20—N5—H5A | 107.9 |
| N1—C2—C1 | 112.2 (2) | C20—N5—C19 | 111.5 (2) |
| N1—C2—C3 | 120.6 (3) | Ni2—N6—H6A | 110.4 |
| C3—C2—C1 | 127.2 (3) | Ni2—N6—H6B | 110.4 |
| C2—C3—H3 | 120.9 | H6A—N6—H6B | 108.6 |
| C2—C3—C4 | 118.1 (3) | C21—N6—Ni2 | 106.50 (18) |
| C4—C3—H3 | 120.9 | C21—N6—H6A | 110.4 |
| C3—C4—H4 | 119.9 | C21—N6—H6B | 110.4 |
| C5—C4—C3 | 120.2 (3) | N3—C15—H15A | 110.1 |
| C5—C4—H4 | 119.9 | N3—C15—H15B | 110.1 |
| C4—C5—H5 | 120.8 | N3—C15—C16 | 108.1 (3) |
| C6—C5—C4 | 118.4 (3) | H15A—C15—H15B | 108.4 |
| C6—C5—H5 | 120.8 | C16—C15—H15A | 110.1 |
| N1—C6—C5 | 120.6 (3) | C16—C15—H15B | 110.1 |
| N1—C6—C7 | 112.8 (2) | N4—C16—C15 | 109.7 (3) |
| C5—C6—C7 | 126.6 (3) | N4—C16—H16A | 109.7 |
| O3—C7—C6 | 114.0 (3) | N4—C16—H16B | 109.7 |
| O4—C7—O3 | 126.7 (3) | C15—C16—H16A | 109.7 |
| O4—C7—C6 | 119.3 (3) | C15—C16—H16B | 109.7 |
| O5—C8—C9 | 115.1 (2) | H16A—C16—H16B | 108.2 |
| O6—C8—O5 | 126.8 (3) | N4—C17—H17A | 109.0 |
| O6—C8—C9 | 118.0 (3) | N4—C17—H17B | 109.0 |
| N2—C9—C8 | 112.7 (2) | N4—C17—C18 | 112.8 (3) |
| N2—C9—C10 | 120.9 (3) | H17A—C17—H17B | 107.8 |
| C10—C9—C8 | 126.4 (3) | C18—C17—H17A | 109.0 |
| C9—C10—H10 | 120.8 | C18—C17—H17B | 109.0 |
| C11—C10—C9 | 118.3 (3) | C17—C18—H18A | 108.2 |
| C11—C10—H10 | 120.8 | C17—C18—H18B | 108.2 |
| C10—C11—H11 | 119.9 | C17—C18—C19 | 116.3 (3) |
| C10—C11—C12 | 120.1 (3) | H18A—C18—H18B | 107.4 |
| C12—C11—H11 | 119.9 | C19—C18—H18A | 108.2 |
| C11—C12—H12 | 120.8 | C19—C18—H18B | 108.2 |
| C13—C12—C11 | 118.4 (3) | N5—C19—C18 | 112.9 (3) |
| C13—C12—H12 | 120.8 | N5—C19—H19A | 109.0 |
| N2—C13—C12 | 120.2 (3) | N5—C19—H19B | 109.0 |
| N2—C13—C14 | 113.4 (2) | C18—C19—H19A | 109.0 |
| C12—C13—C14 | 126.4 (3) | C18—C19—H19B | 109.0 |
| O7—C14—C13 | 114.2 (3) | H19A—C19—H19B | 107.8 |
| O8—C14—O7 | 126.3 (3) | N5—C20—H20A | 109.9 |
| O8—C14—C13 | 119.5 (3) | N5—C20—H20B | 109.9 |
| O2W—Ni2—O1W | 174.88 (8) | N5—C20—C21 | 109.1 (2) |
| N3—Ni2—O1W | 86.26 (9) | H20A—C20—H20B | 108.3 |
| N3—Ni2—O2W | 92.25 (9) | C21—C20—H20A | 109.9 |
| N3—Ni2—N4 | 84.10 (10) | C21—C20—H20B | 109.9 |
| N3—Ni2—N5 | 174.54 (10) | N6—C21—C20 | 109.4 (2) |
| N3—Ni2—N6 | 101.01 (10) | N6—C21—H21A | 109.8 |
| N4—Ni2—O1W | 87.83 (9) | N6—C21—H21B | 109.8 |
| N4—Ni2—O2W | 96.90 (9) | C20—C21—H21A | 109.8 |
| N4—Ni2—N5 | 90.45 (10) | C20—C21—H21B | 109.8 |
| N4—Ni2—N6 | 172.57 (10) | H21A—C21—H21B | 108.2 |
| Ni1—O1—C1—O2 | 175.1 (2) | C2—C3—C4—C5 | 3.0 (4) |
| Ni1—O1—C1—C2 | −6.2 (3) | C3—C4—C5—C6 | −0.7 (4) |
| Ni1—O3—C7—O4 | 175.0 (3) | C4—C5—C6—N1 | −1.7 (4) |
| Ni1—O3—C7—C6 | −5.5 (3) | C4—C5—C6—C7 | 177.3 (3) |
| Ni1—O5—C8—O6 | 179.7 (2) | C5—C6—C7—O3 | −174.5 (3) |
| Ni1—O5—C8—C9 | −2.3 (3) | C5—C6—C7—O4 | 5.0 (5) |
| Ni1—O7—C14—O8 | 171.5 (2) | C6—N1—C2—C1 | −179.3 (2) |
| Ni1—O7—C14—C13 | −10.1 (3) | C6—N1—C2—C3 | 0.7 (4) |
| Ni1—N1—C2—C1 | 4.6 (3) | C8—C9—C10—C11 | 178.3 (3) |
| Ni1—N1—C2—C3 | −175.4 (2) | C9—N2—C13—C12 | −0.7 (4) |
| Ni1—N1—C6—C5 | 177.8 (2) | C9—N2—C13—C14 | −178.9 (3) |
| Ni1—N1—C6—C7 | −1.4 (3) | C9—C10—C11—C12 | −0.4 (4) |
| Ni1—N2—C9—C8 | 2.9 (3) | C10—C11—C12—C13 | 0.6 (5) |
| Ni1—N2—C9—C10 | −178.3 (2) | C11—C12—C13—N2 | −0.1 (4) |
| Ni1—N2—C13—C12 | 178.5 (2) | C11—C12—C13—C14 | 177.9 (3) |
| Ni1—N2—C13—C14 | 0.3 (3) | C12—C13—C14—O7 | −171.3 (3) |
| O1—C1—C2—N1 | 1.4 (4) | C12—C13—C14—O8 | 7.2 (5) |
| O1—C1—C2—C3 | −178.6 (3) | C13—N2—C9—C8 | −177.9 (2) |
| O2—C1—C2—N1 | −179.8 (3) | C13—N2—C9—C10 | 1.0 (4) |
| O2—C1—C2—C3 | 0.2 (5) | Ni2—N3—C15—C16 | 45.9 (3) |
| O5—C8—C9—N2 | −0.2 (4) | Ni2—N4—C16—C15 | 34.9 (3) |
| O5—C8—C9—C10 | −178.9 (3) | Ni2—N4—C17—C18 | −59.1 (3) |
| O6—C8—C9—N2 | 178.0 (3) | Ni2—N5—C19—C18 | 60.4 (3) |
| O6—C8—C9—C10 | −0.8 (4) | Ni2—N5—C20—C21 | −41.5 (3) |
| N1—C2—C3—C4 | −3.0 (4) | Ni2—N6—C21—C20 | −40.1 (3) |
| N1—C6—C7—O3 | 4.6 (4) | N3—C15—C16—N4 | −55.3 (3) |
| N1—C6—C7—O4 | −175.8 (3) | N4—C17—C18—C19 | 65.8 (4) |
| N2—C9—C10—C11 | −0.4 (4) | N5—C20—C21—N6 | 56.4 (3) |
| N2—C13—C14—O7 | 6.8 (4) | C16—N4—C17—C18 | 176.1 (3) |
| N2—C13—C14—O8 | −174.7 (3) | C17—N4—C16—C15 | 164.3 (3) |
| C1—C2—C3—C4 | 177.0 (3) | C17—C18—C19—N5 | −67.0 (4) |
| C2—N1—C6—C5 | 1.8 (4) | C19—N5—C20—C21 | −167.8 (3) |
| C2—N1—C6—C7 | −177.4 (3) | C20—N5—C19—C18 | −178.4 (3) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3A···O8i | 0.91 | 2.41 | 3.213 (3) | 147 |
| N3—H3B···O4ii | 0.91 | 2.11 | 3.015 (3) | 176 |
| N4—H4A···O1 | 1.00 | 2.07 | 3.054 (3) | 167 |
| N5—H5A···O2 | 1.00 | 2.08 | 3.054 (3) | 163 |
| N6—H6A···O3ii | 0.91 | 2.14 | 2.986 (3) | 154 |
| N6—H6B···O6iii | 0.91 | 2.07 | 2.943 (3) | 160 |
| O1W—H1WA···O1 | 0.86 | 2.56 | 3.088 (3) | 121 |
| O1W—H1WA···O2 | 0.86 | 2.00 | 2.795 (3) | 154 |
| O1W—H1WB···O3ii | 0.86 | 1.91 | 2.757 (3) | 170 |
| O2W—H2WA···O7i | 0.87 | 1.80 | 2.663 (3) | 169 |
| O2W—H2WB···O6iii | 0.87 | 1.90 | 2.742 (3) | 160 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989021011178/hb7995sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021011178/hb7995Isup2.hkl
CCDC reference: 2115829
Additional supporting information: crystallographic information; 3D view; checkCIF report