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Acta Cryst. (2010). E66, m642-m643    [ doi:10.1107/S1600536810016776 ]

Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato-[kappa]3O2,N,O6)nickelate(II) trihydrate

Z. Derikvand and M. M. Olmstead

Abstract top

The title compound, (C13H11N2)2[Ni(C7H3NO4)2]·3H2O, consists of a mononuclear anionic complex, two 9-aminoacridinium cations and three uncoordinated water molecules. Two pyridine-2,6-dicarboxylate (pydc) ligands are bound to the NiII ion, giving an NiN2O4 bonded set. The coordination geometry around the NiII atom is distorted octahedral. There are two types of robust O-H...O hydrogen-bond synthons, namely R66(24) and R24(8), which link the complex anions and water molecules to each other. N-H...O hydrogen bonds connect the stacks of anions and cations in the structure. Other intermolecular interactions, including weak C-H...O hydrogen bonds, [pi]-[pi] [shortest centroid-centroid distance = 3.336 (7) Å] and C-O...[pi] [O...centroid distance = 3.562 (10) Å] interactions, connect the various components.

Comment top

9-Aminoacridine is a highly fluorescent dye clinically used as a topical antiseptic and experimentally as a mutagen, an intracellular pH indicator and as a MALDI matrix. Acridine and related derivatives bind to DNA and RNA due to their abilities to intercalate. Many complexes containing pyridine-2,6-dicarboxylate (pydc), NiII ions and various bases have been reported (Aghabozorg et al., 2008, 2009; Attar Gharamaleki et al., 2009; Cui et al., 2009; Hadadzadeh et al., 2010; Safaei-Ghomi et al., 2009).

The asymmetric unit of the title compound consists of one [Ni(pydc)2]2- anion, two 9-aminoacridinuum cations and three uncoordinated water molecules (Fig. 1). In the synthesis, two carboxylic acid protons are transferred to the endocyclic N atoms of 9-aminoacridines. Two pydc ligands are bound to the metal ion to give a NiN2O4 bonded set, using all the coordination sites of the pydc ligand. The resulting coordination polyhedron can be described as distorted octahedral. In the anionic complex, the Ni—N bond distances [1.9648 (8) and 1.9760 (8) Å] are shorter than the Ni—O bond distances [2.1003 (7), 2.1120 (7), 2.1360 (7) and 2.1776 (7) Å]. It is worth pointing out that there are two types of robust hydrogen bond synthons, namely R66(24) and R24(8), which link the complex anions and water molecules to each other, as shown in Fig. 2. The dihedral angle between two coordinated pydc ligands is 85.14 (3)°, which shows that two ligands are almost perpendicular to each other. A feature of the title compound is the presence of π–π and C—O···π interactions. The shortest π–π distance is 3.336 (7) Å and C—O···π distances is 3.562 (10) Å (Fig. 3). Another feature in this crystal structure is intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds with D···A distances ranging from 2.6903 (11) to 3.3386 (12)Å (Table 1).

The packing consists of distinctive stacks of cations and anions that propagate along the a direction. These stacks are connected to each other by N—H···O hydrogen bonds, as shown in Fig. 4. This crystal structure is comparable to (H3O)+(creatH)+[Ni(pydc)2].3H2O (creat = creatinine) (Attar Gharamaleki et al., 2009).

Related literature top

For related structures containing [Ni(pydc)2]2- species, see: Aghabozorg et al. (2008, 2009); Attar Gharamaleki et al. (2009); Cui et al. (2009); Hadadzadeh et al. (2010); Safaei-Ghomi et al. (2009).

Experimental top

An aqueous solution of Ni(NO3)2.6H2O (145 mg, 0.5 mmol) in distilled water (5 ml) was added to methanolic solution of pyridine-2,6-dicarboxylic acid (167 mg, 1 mmol) in water (20 ml) and 9-aminoacridine (194 mg, 1 mmol) in methanol (5 ml) under stirring at 80°C in a 1:2:2 molar ratio. The green colored precipitated product was obtained. The precipitation was dissolved in solution of H2O/DMSO in a volume ratio of 1:2 (5/10 ml). Green block crystals, suitable for X-ray characterization, were obtained after 4 d at room temperature.

Refinement top

All H atoms were located in difference Fourier maps and refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. A view of the two types of robust hydrogen bond synthons, R66(24) and R24(8), which link the complex anions and water molecules to each other.
[Figure 3] Fig. 3. A view of the extensive π–π stacking interactions (dashed lines) between aromatic rings of 9-aminoacridinium ions and the C—O···π interaction (dashed line) between C7—O3 and the centroid of the pyridyl ring of a neighboring pydc ligand. [Distances: (i) 3.336; (ii) 3.834; (iii) 3.429; (iv) 3.621; (v) 3.562 Å.]
[Figure 4] Fig. 4. A view showing how the cations and anions are connected by N—H···O hydrogen bonds (dashed lines).
Bis(9-aminoacridinium) bis(pyridine-2,6-dicarboxylato- κ3O2,N,O6)nickelate(II) trihydrate top
Crystal data top
(C13H11N2)2[Ni(C7H3NO4)2]·3H2OZ = 2
Mr = 833.44F(000) = 864
Triclinic, P1Dx = 1.542 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7939 (10) ÅCell parameters from 9659 reflections
b = 13.3335 (12) Åθ = 2.9–31.5°
c = 13.9370 (13) ŵ = 0.62 mm−1
α = 102.288 (2)°T = 90 K
β = 103.609 (2)°Block, green
γ = 105.482 (2)°0.36 × 0.24 × 0.20 mm
V = 1795.6 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer		11816 independent reflections
Radiation source: fine-focus sealed tube10951 reflections with I > 2σ(I)
graphiteRint = 0.015
Detector resolution: 0.83 pixels mm-1θmax = 31.5°, θmin = 2.8°
φ and ω scansh = −15→15
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −19→19
Tmin = 0.809, Tmax = 0.887l = −20→20
29993 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: difference Fourier map
wR(F2) = 0.076All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0406P)2 + 0.6602P]
where P = (Fo2 + 2Fc2)/3
11816 reflections(Δ/σ)max = 0.008
659 parametersΔρmax = 0.48 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
(C13H11N2)2[Ni(C7H3NO4)2]·3H2Oγ = 105.482 (2)°
Mr = 833.44V = 1795.6 (3) Å3
Triclinic, P1Z = 2
a = 10.7939 (10) ÅMo Kα radiation
b = 13.3335 (12) ŵ = 0.62 mm−1
c = 13.9370 (13) ÅT = 90 K
α = 102.288 (2)°0.36 × 0.24 × 0.20 mm
β = 103.609 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		11816 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		10951 reflections with I > 2σ(I)
Tmin = 0.809, Tmax = 0.887Rint = 0.015
29993 measured reflectionsθmax = 31.5°
Refinement top
R[F2 > 2σ(F2)] = 0.027All H-atom parameters refined
wR(F2) = 0.076Δρmax = 0.48 e Å−3
S = 1.04Δρmin = −0.34 e Å−3
11816 reflectionsAbsolute structure: ?
659 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.359601 (12)0.243203 (9)0.083985 (9)0.01101 (3)
O10.24161 (7)0.20633 (6)0.18019 (5)0.01602 (13)
O20.09729 (8)0.06546 (6)0.20554 (6)0.01894 (14)
O30.47436 (8)0.07283 (6)−0.14184 (5)0.01698 (13)
O40.45471 (7)0.21101 (5)−0.02971 (5)0.01462 (12)
O50.54671 (7)0.27912 (6)0.20078 (5)0.01500 (12)
O60.73195 (8)0.42266 (7)0.30005 (6)0.02066 (15)
O70.14490 (7)0.42729 (6)−0.04067 (5)0.01533 (13)
O80.20247 (7)0.28295 (5)−0.01471 (5)0.01506 (12)
N10.28850 (8)0.08335 (6)0.03374 (6)0.01215 (13)
N20.43332 (8)0.40357 (6)0.11994 (6)0.01076 (13)
C10.17544 (10)0.10551 (8)0.16048 (7)0.01420 (16)
C20.20048 (9)0.02963 (7)0.07382 (7)0.01305 (15)
C30.14477 (10)−0.08340 (8)0.03748 (8)0.01671 (17)
H30.0808 (16)−0.1233 (13)0.0667 (12)0.026 (4)*
C40.18596 (11)−0.13846 (8)−0.03952 (8)0.01748 (17)
H40.1504 (15)−0.2174 (13)−0.0647 (12)0.023 (4)*
C50.27985 (10)−0.08048 (8)−0.07890 (7)0.01533 (16)
H50.3120 (16)−0.1156 (13)−0.1310 (12)0.024 (4)*
C60.32823 (9)0.03235 (7)−0.04062 (7)0.01215 (15)
C70.42722 (9)0.11096 (7)−0.07411 (7)0.01279 (15)
C80.61936 (10)0.37940 (8)0.23293 (7)0.01360 (15)
C90.55891 (9)0.45375 (7)0.18393 (7)0.01160 (15)
C100.62363 (9)0.56455 (8)0.20244 (7)0.01367 (15)
H100.7148 (16)0.5980 (13)0.2491 (12)0.025 (4)*
C110.55385 (10)0.62207 (7)0.15184 (7)0.01395 (16)
H110.5949 (15)0.6953 (12)0.1617 (11)0.019 (3)*
C120.42193 (9)0.56827 (7)0.08503 (7)0.01255 (15)
H120.3741 (15)0.6076 (12)0.0478 (11)0.019 (3)*
C130.36452 (9)0.45752 (7)0.07089 (7)0.01066 (14)
C140.22569 (9)0.38391 (7)−0.00075 (7)0.01211 (15)
N31.01535 (9)0.30800 (7)0.73932 (6)0.01601 (15)
H3A1.0262 (18)0.2447 (15)0.7348 (13)0.035 (4)*
H3B1.0349 (16)0.3518 (14)0.8016 (13)0.028 (4)*
N40.85905 (8)0.38995 (6)0.47807 (6)0.01216 (13)
H4A0.8176 (17)0.4019 (13)0.4211 (13)0.029 (4)*
C150.96750 (9)0.33591 (7)0.65564 (7)0.01238 (15)
C160.92971 (9)0.43231 (7)0.66353 (7)0.01277 (15)
C170.94175 (10)0.50324 (8)0.75957 (7)0.01699 (17)
H170.9776 (15)0.4885 (12)0.8207 (12)0.022 (4)*
C180.89975 (11)0.59228 (8)0.76344 (8)0.01865 (18)
H180.9081 (15)0.6410 (12)0.8279 (12)0.023 (4)*
C190.84486 (10)0.61508 (8)0.67144 (8)0.01701 (17)
H190.8169 (17)0.6750 (13)0.6743 (13)0.029 (4)*
C200.83206 (10)0.54841 (8)0.57722 (8)0.01467 (16)
H200.7949 (15)0.5620 (12)0.5123 (12)0.024 (4)*
C210.87392 (9)0.45595 (7)0.57219 (7)0.01210 (15)
C220.89545 (9)0.29898 (7)0.46724 (7)0.01138 (14)
C230.87734 (9)0.23509 (8)0.36660 (7)0.01369 (15)
H230.8404 (15)0.2582 (12)0.3080 (11)0.019 (3)*
C240.91252 (10)0.14290 (8)0.35392 (7)0.01527 (16)
H240.9000 (16)0.1003 (13)0.2858 (12)0.027 (4)*
C250.96692 (9)0.11129 (8)0.44075 (8)0.01504 (16)
H250.9882 (15)0.0445 (12)0.4304 (11)0.021 (4)*
C260.98706 (9)0.17326 (8)0.53888 (7)0.01362 (15)
H261.0261 (15)0.1520 (12)0.5973 (11)0.020 (3)*
C270.95095 (9)0.26932 (7)0.55488 (7)0.01163 (15)
N50.54540 (8)0.10654 (7)0.29830 (6)0.01346 (14)
H5B0.5307 (17)0.1587 (14)0.2716 (12)0.028 (4)*
H5A0.5530 (17)0.0488 (14)0.2569 (13)0.032 (4)*
N60.66618 (8)0.17508 (7)0.61591 (6)0.01321 (14)
H6A0.6815 (18)0.1842 (14)0.6793 (14)0.035 (4)*
C280.58088 (9)0.12538 (7)0.39986 (7)0.01094 (14)
C290.63617 (9)0.05563 (7)0.44931 (7)0.01157 (14)
C300.65177 (9)−0.04016 (7)0.39368 (7)0.01397 (15)
H300.6252 (15)−0.0608 (12)0.3218 (12)0.020 (3)*
C310.70392 (10)−0.10461 (8)0.44482 (8)0.01636 (17)
H310.7130 (15)−0.1690 (13)0.4074 (12)0.021 (3)*
C320.74404 (9)−0.07552 (8)0.55373 (8)0.01687 (17)
H320.7815 (15)−0.1210 (12)0.5896 (12)0.023 (4)*
C330.73293 (9)0.01756 (8)0.61017 (8)0.01544 (16)
H330.7632 (16)0.0396 (13)0.6863 (12)0.027 (4)*
C340.67789 (9)0.08377 (7)0.55852 (7)0.01229 (15)
C350.60723 (9)0.23954 (7)0.57198 (7)0.01228 (15)
C360.58907 (10)0.32831 (8)0.63673 (7)0.01603 (17)
H360.6224 (16)0.3430 (13)0.7095 (13)0.027 (4)*
C370.52273 (11)0.38982 (8)0.59321 (8)0.01782 (17)
H370.5095 (16)0.4525 (13)0.6367 (12)0.026 (4)*
C380.47143 (10)0.36511 (8)0.48487 (8)0.01641 (17)
H380.4195 (15)0.4061 (12)0.4546 (11)0.021 (4)*
C390.49140 (9)0.28085 (7)0.42143 (7)0.01346 (15)
H390.4518 (14)0.2641 (12)0.3479 (11)0.017 (3)*
C400.56196 (9)0.21681 (7)0.46364 (7)0.01130 (14)
O1W0.11651 (8)0.63289 (6)0.02097 (6)0.01961 (14)
H1A0.132 (2)0.5745 (16)0.0089 (15)0.045 (5)*
H1B0.0366 (19)0.6155 (14)0.0272 (13)0.033 (4)*
O2W−0.08266 (9)−0.12483 (7)0.21495 (6)0.02072 (15)
H2A−0.1191 (18)−0.1637 (15)0.1557 (14)0.033 (4)*
H2B−0.031 (2)−0.0729 (16)0.2114 (15)0.041 (5)*
O3W0.68638 (9)0.20630 (7)0.81693 (6)0.02351 (16)
H3C0.628 (2)0.1734 (16)0.8358 (14)0.039 (5)*
H3D0.7472 (19)0.2544 (15)0.8698 (14)0.035 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01530 (6)0.00874 (5)0.01001 (5)0.00488 (4)0.00442 (4)0.00317 (4)
O10.0215 (3)0.0127 (3)0.0155 (3)0.0059 (3)0.0089 (3)0.0036 (2)
O20.0230 (3)0.0193 (3)0.0185 (3)0.0069 (3)0.0120 (3)0.0076 (3)
O30.0217 (3)0.0153 (3)0.0143 (3)0.0052 (3)0.0095 (3)0.0019 (2)
O40.0214 (3)0.0106 (3)0.0139 (3)0.0057 (2)0.0081 (2)0.0042 (2)
O50.0196 (3)0.0138 (3)0.0142 (3)0.0080 (2)0.0048 (2)0.0067 (2)
O60.0178 (3)0.0236 (4)0.0188 (3)0.0065 (3)−0.0008 (3)0.0105 (3)
O70.0145 (3)0.0158 (3)0.0152 (3)0.0072 (2)0.0014 (2)0.0044 (2)
O80.0166 (3)0.0112 (3)0.0148 (3)0.0038 (2)0.0018 (2)0.0030 (2)
N10.0163 (3)0.0105 (3)0.0107 (3)0.0052 (3)0.0048 (3)0.0036 (3)
N20.0133 (3)0.0105 (3)0.0097 (3)0.0054 (3)0.0039 (3)0.0033 (2)
C10.0173 (4)0.0153 (4)0.0121 (4)0.0071 (3)0.0054 (3)0.0050 (3)
C20.0164 (4)0.0120 (4)0.0121 (4)0.0051 (3)0.0053 (3)0.0050 (3)
C30.0208 (4)0.0128 (4)0.0166 (4)0.0036 (3)0.0074 (3)0.0052 (3)
C40.0230 (5)0.0107 (4)0.0166 (4)0.0031 (3)0.0063 (3)0.0029 (3)
C50.0212 (4)0.0113 (4)0.0131 (4)0.0053 (3)0.0055 (3)0.0026 (3)
C60.0162 (4)0.0107 (3)0.0101 (3)0.0051 (3)0.0042 (3)0.0033 (3)
C70.0165 (4)0.0121 (4)0.0105 (3)0.0052 (3)0.0044 (3)0.0041 (3)
C80.0162 (4)0.0161 (4)0.0122 (4)0.0082 (3)0.0054 (3)0.0071 (3)
C90.0138 (4)0.0126 (4)0.0101 (3)0.0058 (3)0.0041 (3)0.0046 (3)
C100.0135 (4)0.0137 (4)0.0127 (4)0.0035 (3)0.0028 (3)0.0043 (3)
C110.0161 (4)0.0113 (4)0.0147 (4)0.0040 (3)0.0049 (3)0.0048 (3)
C120.0151 (4)0.0116 (4)0.0130 (4)0.0062 (3)0.0050 (3)0.0048 (3)
C130.0124 (4)0.0107 (3)0.0097 (3)0.0051 (3)0.0036 (3)0.0032 (3)
C140.0132 (4)0.0129 (4)0.0101 (3)0.0045 (3)0.0034 (3)0.0033 (3)
N30.0186 (4)0.0169 (4)0.0116 (3)0.0068 (3)0.0016 (3)0.0047 (3)
N40.0133 (3)0.0124 (3)0.0116 (3)0.0051 (3)0.0034 (3)0.0045 (3)
C150.0101 (3)0.0132 (4)0.0124 (4)0.0028 (3)0.0022 (3)0.0039 (3)
C160.0118 (4)0.0128 (4)0.0125 (4)0.0035 (3)0.0027 (3)0.0031 (3)
C170.0185 (4)0.0167 (4)0.0134 (4)0.0055 (3)0.0031 (3)0.0022 (3)
C180.0203 (4)0.0162 (4)0.0168 (4)0.0055 (3)0.0052 (3)0.0008 (3)
C190.0168 (4)0.0133 (4)0.0206 (4)0.0056 (3)0.0064 (3)0.0029 (3)
C200.0142 (4)0.0130 (4)0.0178 (4)0.0054 (3)0.0050 (3)0.0054 (3)
C210.0107 (3)0.0116 (4)0.0135 (4)0.0032 (3)0.0038 (3)0.0036 (3)
C220.0101 (3)0.0120 (3)0.0125 (4)0.0036 (3)0.0038 (3)0.0044 (3)
C230.0142 (4)0.0154 (4)0.0121 (4)0.0054 (3)0.0043 (3)0.0046 (3)
C240.0156 (4)0.0162 (4)0.0149 (4)0.0064 (3)0.0062 (3)0.0034 (3)
C250.0136 (4)0.0147 (4)0.0186 (4)0.0066 (3)0.0059 (3)0.0049 (3)
C260.0119 (4)0.0143 (4)0.0160 (4)0.0055 (3)0.0042 (3)0.0060 (3)
C270.0100 (3)0.0124 (4)0.0124 (4)0.0036 (3)0.0030 (3)0.0043 (3)
N50.0185 (4)0.0127 (3)0.0107 (3)0.0076 (3)0.0045 (3)0.0037 (3)
N60.0130 (3)0.0163 (3)0.0101 (3)0.0042 (3)0.0037 (3)0.0043 (3)
C280.0096 (3)0.0113 (3)0.0118 (3)0.0029 (3)0.0037 (3)0.0035 (3)
C290.0105 (3)0.0121 (4)0.0128 (4)0.0038 (3)0.0038 (3)0.0049 (3)
C300.0131 (4)0.0127 (4)0.0165 (4)0.0047 (3)0.0045 (3)0.0047 (3)
C310.0142 (4)0.0140 (4)0.0228 (4)0.0058 (3)0.0060 (3)0.0075 (3)
C320.0121 (4)0.0184 (4)0.0235 (5)0.0054 (3)0.0056 (3)0.0126 (4)
C330.0120 (4)0.0197 (4)0.0167 (4)0.0048 (3)0.0042 (3)0.0105 (3)
C340.0095 (3)0.0145 (4)0.0130 (4)0.0027 (3)0.0037 (3)0.0057 (3)
C350.0112 (3)0.0132 (4)0.0117 (4)0.0025 (3)0.0045 (3)0.0032 (3)
C360.0180 (4)0.0159 (4)0.0127 (4)0.0037 (3)0.0067 (3)0.0016 (3)
C370.0224 (4)0.0149 (4)0.0179 (4)0.0068 (3)0.0107 (4)0.0026 (3)
C380.0186 (4)0.0141 (4)0.0191 (4)0.0072 (3)0.0083 (3)0.0052 (3)
C390.0145 (4)0.0131 (4)0.0141 (4)0.0054 (3)0.0054 (3)0.0046 (3)
C400.0112 (3)0.0115 (3)0.0113 (3)0.0036 (3)0.0042 (3)0.0030 (3)
O1W0.0175 (3)0.0149 (3)0.0243 (4)0.0041 (3)0.0058 (3)0.0040 (3)
O2W0.0258 (4)0.0174 (3)0.0157 (3)0.0039 (3)0.0037 (3)0.0055 (3)
O3W0.0238 (4)0.0272 (4)0.0120 (3)−0.0023 (3)0.0057 (3)0.0041 (3)
Geometric parameters (Å, °) top
Ni1—N11.9648 (8)C18—H180.959 (15)
Ni1—N21.9760 (8)C19—C201.3732 (14)
Ni1—O12.1003 (7)C19—H190.923 (17)
Ni1—O42.1120 (7)C20—C211.4158 (12)
Ni1—O52.1360 (7)C20—H200.974 (15)
Ni1—O82.1776 (7)C22—C271.4124 (12)
O1—C11.2770 (12)C22—C231.4158 (12)
O2—C11.2420 (12)C23—C241.3692 (13)
O3—C71.2523 (11)C23—H230.969 (15)
O4—C71.2655 (11)C24—C251.4148 (13)
O5—C81.2741 (12)C24—H240.955 (16)
O6—C81.2434 (12)C25—C261.3725 (13)
O7—C141.2580 (11)C25—H250.968 (15)
O8—C141.2642 (11)C26—C271.4240 (12)
N1—C21.3359 (12)C26—H260.960 (15)
N1—C61.3361 (11)N5—C281.3249 (11)
N2—C91.3318 (12)N5—H5B0.889 (17)
N2—C131.3385 (11)N5—H5A0.894 (17)
C1—C21.5280 (13)N6—C351.3606 (12)
C2—C31.3919 (13)N6—C341.3613 (12)
C3—C41.3970 (14)N6—H6A0.836 (18)
C3—H30.977 (16)C28—C291.4393 (12)
C4—C51.3963 (14)C28—C401.4405 (12)
C4—H40.971 (16)C29—C341.4157 (12)
C5—C61.3888 (12)C29—C301.4197 (12)
C5—H50.963 (16)C30—C311.3760 (13)
C6—C71.5176 (13)C30—H300.930 (15)
C8—C91.5162 (12)C31—C321.4116 (14)
C9—C101.3925 (13)C31—H310.947 (15)
C10—C111.3934 (13)C32—C331.3717 (14)
C10—H100.965 (16)C32—H320.973 (15)
C11—C121.3984 (13)C33—C341.4141 (13)
C11—H110.923 (15)C33—H330.985 (16)
C12—C131.3906 (12)C35—C401.4104 (12)
C12—H120.971 (15)C35—C361.4163 (13)
C13—C141.5164 (12)C36—C371.3691 (14)
N3—C151.3301 (12)C36—H360.950 (16)
N3—H3A0.873 (18)C37—C381.4116 (14)
N3—H3B0.878 (17)C37—H370.987 (16)
N4—C221.3612 (11)C38—C391.3736 (13)
N4—C211.3620 (12)C38—H380.970 (15)
N4—H4A0.884 (17)C39—C401.4161 (12)
C15—C271.4349 (12)C39—H390.963 (14)
C15—C161.4392 (13)O1W—H1A0.83 (2)
C16—C211.4121 (12)O1W—H1B0.861 (19)
C16—C171.4201 (13)O2W—H2A0.813 (19)
C17—C181.3746 (14)O2W—H2B0.79 (2)
C17—H170.934 (15)O3W—H3C0.79 (2)
C18—C191.4115 (15)O3W—H3D0.856 (19)
N1—Ni1—N2173.93 (3)C18—C17—H17119.7 (9)
N1—Ni1—O178.42 (3)C16—C17—H17119.4 (9)
N2—Ni1—O1107.10 (3)C17—C18—C19120.21 (9)
N1—Ni1—O478.42 (3)C17—C18—H18121.5 (9)
N2—Ni1—O496.15 (3)C19—C18—H18118.3 (9)
O1—Ni1—O4156.71 (3)C20—C19—C18120.50 (9)
N1—Ni1—O5104.16 (3)C20—C19—H19119.5 (10)
N2—Ni1—O578.28 (3)C18—C19—H19120.0 (10)
O1—Ni1—O594.00 (3)C19—C20—C21119.82 (9)
O4—Ni1—O589.26 (3)C19—C20—H20122.5 (9)
N1—Ni1—O8100.69 (3)C21—C20—H20117.6 (9)
N2—Ni1—O876.88 (3)N4—C21—C16120.52 (8)
O1—Ni1—O892.00 (3)N4—C21—C20119.08 (8)
O4—Ni1—O894.68 (3)C16—C21—C20120.40 (8)
O5—Ni1—O8155.12 (3)N4—C22—C27120.54 (8)
C1—O1—Ni1115.38 (6)N4—C22—C23118.77 (8)
C7—O4—Ni1114.59 (6)C27—C22—C23120.69 (8)
C8—O5—Ni1114.08 (6)C24—C23—C22119.72 (8)
C14—O8—Ni1114.13 (6)C24—C23—H23121.5 (9)
C2—N1—C6122.34 (8)C22—C23—H23118.8 (9)
C2—N1—Ni1118.90 (6)C23—C24—C25120.38 (9)
C6—N1—Ni1118.75 (6)C23—C24—H24119.2 (10)
C9—N2—C13121.37 (8)C25—C24—H24120.4 (10)
C9—N2—Ni1118.02 (6)C26—C25—C24120.59 (9)
C13—N2—Ni1120.08 (6)C26—C25—H25120.0 (9)
O2—C1—O1126.47 (9)C24—C25—H25119.4 (9)
O2—C1—C2118.90 (8)C25—C26—C27120.51 (8)
O1—C1—C2114.61 (8)C25—C26—H26119.9 (9)
N1—C2—C3120.31 (8)C27—C26—H26119.6 (9)
N1—C2—C1112.49 (8)C22—C27—C26118.10 (8)
C3—C2—C1127.18 (8)C22—C27—C15119.12 (8)
C2—C3—C4118.28 (9)C26—C27—C15122.79 (8)
C2—C3—H3120.8 (9)C28—N5—H5B119.4 (10)
C4—C3—H3120.9 (9)C28—N5—H5A121.4 (11)
C5—C4—C3120.26 (9)H5B—N5—H5A117.9 (15)
C5—C4—H4119.9 (9)C35—N6—C34122.20 (8)
C3—C4—H4119.8 (9)C35—N6—H6A118.9 (12)
C6—C5—C4118.08 (9)C34—N6—H6A117.8 (12)
C6—C5—H5119.2 (9)N5—C28—C29121.91 (8)
C4—C5—H5122.7 (9)N5—C28—C40119.80 (8)
N1—C6—C5120.68 (8)C29—C28—C40118.29 (8)
N1—C6—C7112.46 (8)C34—C29—C30118.18 (8)
C5—C6—C7126.86 (8)C34—C29—C28118.75 (8)
O3—C7—O4125.73 (9)C30—C29—C28123.06 (8)
O3—C7—C6118.52 (8)C31—C30—C29120.68 (9)
O4—C7—C6115.76 (8)C31—C30—H30119.1 (9)
O6—C8—O5127.62 (9)C29—C30—H30120.2 (9)
O6—C8—C9117.00 (8)C30—C31—C32120.25 (9)
O5—C8—C9115.38 (8)C30—C31—H31120.4 (9)
N2—C9—C10121.18 (8)C32—C31—H31119.3 (9)
N2—C9—C8113.61 (8)C33—C32—C31120.72 (9)
C10—C9—C8125.21 (8)C33—C32—H32119.3 (9)
C9—C10—C11118.31 (8)C31—C32—H32120.0 (9)
C9—C10—H10118.8 (9)C32—C33—C34119.59 (9)
C11—C10—H10122.9 (9)C32—C33—H33121.2 (9)
C10—C11—C12119.83 (8)C34—C33—H33119.2 (9)
C10—C11—H11120.2 (9)N6—C34—C33118.67 (8)
C12—C11—H11120.0 (9)N6—C34—C29120.76 (8)
C13—C12—C11118.26 (8)C33—C34—C29120.56 (9)
C13—C12—H12121.7 (9)N6—C35—C40120.56 (8)
C11—C12—H12120.0 (9)N6—C35—C36118.90 (8)
N2—C13—C12121.04 (8)C40—C35—C36120.52 (8)
N2—C13—C14112.51 (7)C37—C36—C35119.41 (9)
C12—C13—C14126.41 (8)C37—C36—H36121.7 (10)
O7—C14—O8125.99 (9)C35—C36—H36118.9 (10)
O7—C14—C13118.26 (8)C36—C37—C38120.74 (9)
O8—C14—C13115.75 (8)C36—C37—H37120.9 (9)
C15—N3—H3A121.6 (12)C38—C37—H37118.3 (9)
C15—N3—H3B121.1 (11)C39—C38—C37120.27 (9)
H3A—N3—H3B117.2 (15)C39—C38—H38119.4 (9)
C22—N4—C21122.33 (8)C37—C38—H38120.3 (9)
C22—N4—H4A117.4 (11)C38—C39—C40120.57 (9)
C21—N4—H4A120.0 (11)C38—C39—H39118.2 (8)
N3—C15—C27120.41 (8)C40—C39—H39121.1 (8)
N3—C15—C16121.15 (8)C35—C40—C39118.39 (8)
C27—C15—C16118.44 (8)C35—C40—C28119.18 (8)
C21—C16—C17118.21 (8)C39—C40—C28122.30 (8)
C21—C16—C15119.03 (8)H1A—O1W—H1B104.2 (17)
C17—C16—C15122.73 (8)H2A—O2W—H2B105.1 (18)
C18—C17—C16120.87 (9)H3C—O3W—H3D108.3 (17)
N1—Ni1—O1—C1−3.81 (7)C9—N2—C13—C14178.01 (8)
N2—Ni1—O1—C1173.57 (7)Ni1—N2—C13—C146.49 (10)
O4—Ni1—O1—C1−10.03 (12)C11—C12—C13—N20.10 (13)
O5—Ni1—O1—C1−107.47 (7)C11—C12—C13—C14−177.60 (8)
O8—Ni1—O1—C196.69 (7)Ni1—O8—C14—O7−172.58 (7)
N1—Ni1—O4—C7−1.21 (7)Ni1—O8—C14—C137.53 (10)
N2—Ni1—O4—C7−178.46 (7)N2—C13—C14—O7170.84 (8)
O1—Ni1—O4—C75.00 (12)C12—C13—C14—O7−11.29 (14)
O5—Ni1—O4—C7103.41 (7)N2—C13—C14—O8−9.27 (11)
O8—Ni1—O4—C7−101.19 (7)C12—C13—C14—O8168.60 (9)
N1—Ni1—O5—C8170.05 (6)N3—C15—C16—C21−177.27 (9)
N2—Ni1—O5—C8−4.26 (6)C27—C15—C16—C212.02 (13)
O1—Ni1—O5—C8−110.90 (6)N3—C15—C16—C170.48 (14)
O4—Ni1—O5—C892.18 (6)C27—C15—C16—C17179.76 (9)
O8—Ni1—O5—C8−7.38 (11)C21—C16—C17—C180.23 (14)
N1—Ni1—O8—C14−177.64 (6)C15—C16—C17—C18−177.54 (9)
N2—Ni1—O8—C14−3.33 (6)C16—C17—C18—C19−0.57 (16)
O1—Ni1—O8—C14103.77 (7)C17—C18—C19—C200.39 (16)
O4—Ni1—O8—C14−98.56 (7)C18—C19—C20—C210.13 (15)
O5—Ni1—O8—C14−0.19 (11)C22—N4—C21—C160.55 (13)
O1—Ni1—N1—C23.91 (7)C22—N4—C21—C20−179.16 (8)
O4—Ni1—N1—C2−178.59 (7)C17—C16—C21—N4−179.41 (8)
O5—Ni1—N1—C295.16 (7)C15—C16—C21—N4−1.56 (13)
O8—Ni1—N1—C2−85.94 (7)C17—C16—C21—C200.30 (13)
O1—Ni1—N1—C6−177.21 (7)C15—C16—C21—C20178.15 (8)
O4—Ni1—N1—C60.29 (7)C19—C20—C21—N4179.24 (9)
O5—Ni1—N1—C6−85.96 (7)C19—C20—C21—C16−0.48 (14)
O8—Ni1—N1—C692.93 (7)C21—N4—C22—C27−0.01 (13)
O1—Ni1—N2—C997.94 (7)C21—N4—C22—C23−179.65 (8)
O4—Ni1—N2—C9−80.63 (7)N4—C22—C23—C24−179.61 (8)
O5—Ni1—N2—C97.33 (6)C27—C22—C23—C240.74 (13)
O8—Ni1—N2—C9−174.02 (7)C22—C23—C24—C25−0.06 (14)
O1—Ni1—N2—C13−90.26 (7)C23—C24—C25—C26−0.96 (14)
O4—Ni1—N2—C1391.17 (7)C24—C25—C26—C271.28 (14)
O5—Ni1—N2—C13179.13 (7)N4—C22—C27—C26179.94 (8)
O8—Ni1—N2—C13−2.22 (6)C23—C22—C27—C26−0.42 (13)
Ni1—O1—C1—O2−178.27 (8)N4—C22—C27—C150.51 (13)
Ni1—O1—C1—C23.09 (10)C23—C22—C27—C15−179.85 (8)
C6—N1—C2—C3−0.99 (14)C25—C26—C27—C22−0.60 (13)
Ni1—N1—C2—C3177.85 (7)C25—C26—C27—C15178.82 (9)
C6—N1—C2—C1177.73 (8)N3—C15—C27—C22177.79 (8)
Ni1—N1—C2—C1−3.44 (10)C16—C15—C27—C22−1.50 (12)
O2—C1—C2—N1−178.73 (9)N3—C15—C27—C26−1.62 (14)
O1—C1—C2—N10.02 (12)C16—C15—C27—C26179.09 (8)
O2—C1—C2—C3−0.13 (15)N5—C28—C29—C34176.98 (8)
O1—C1—C2—C3178.62 (9)C40—C28—C29—C34−4.17 (12)
N1—C2—C3—C41.59 (15)N5—C28—C29—C30−2.62 (14)
C1—C2—C3—C4−176.92 (9)C40—C28—C29—C30176.22 (8)
C2—C3—C4—C5−0.51 (15)C34—C29—C30—C311.09 (13)
C3—C4—C5—C6−1.13 (15)C28—C29—C30—C31−179.30 (9)
C2—N1—C6—C5−0.74 (14)C29—C30—C31—C32−0.67 (14)
Ni1—N1—C6—C5−179.58 (7)C30—C31—C32—C33−0.61 (14)
C2—N1—C6—C7179.35 (8)C31—C32—C33—C341.41 (14)
Ni1—N1—C6—C70.52 (10)C35—N6—C34—C33−176.15 (8)
C4—C5—C6—N11.78 (14)C35—N6—C34—C294.00 (13)
C4—C5—C6—C7−178.33 (9)C32—C33—C34—N6179.19 (8)
Ni1—O4—C7—O3−178.14 (8)C32—C33—C34—C29−0.96 (13)
Ni1—O4—C7—C61.82 (10)C30—C29—C34—N6179.57 (8)
N1—C6—C7—O3178.38 (8)C28—C29—C34—N6−0.06 (13)
C5—C6—C7—O3−1.52 (14)C30—C29—C34—C33−0.28 (13)
N1—C6—C7—O4−1.58 (12)C28—C29—C34—C33−179.91 (8)
C5—C6—C7—O4178.52 (9)C34—N6—C35—C40−3.45 (13)
Ni1—O5—C8—O6179.89 (8)C34—N6—C35—C36175.03 (8)
Ni1—O5—C8—C90.92 (10)N6—C35—C36—C37−176.16 (9)
C13—N2—C9—C100.07 (13)C40—C35—C36—C372.32 (14)
Ni1—N2—C9—C10171.76 (7)C35—C36—C37—C380.56 (15)
C13—N2—C9—C8179.37 (8)C36—C37—C38—C39−2.15 (15)
Ni1—N2—C9—C8−8.94 (10)C37—C38—C39—C400.84 (15)
O6—C8—C9—N2−174.13 (8)N6—C35—C40—C39174.90 (8)
O5—C8—C9—N24.96 (12)C36—C35—C40—C39−3.55 (13)
O6—C8—C9—C105.13 (14)N6—C35—C40—C28−1.02 (13)
O5—C8—C9—C10−175.78 (9)C36—C35—C40—C28−179.47 (8)
N2—C9—C10—C11−0.28 (13)C38—C39—C40—C351.97 (13)
C8—C9—C10—C11−179.49 (8)C38—C39—C40—C28177.75 (9)
C9—C10—C11—C120.39 (14)N5—C28—C40—C35−176.42 (8)
C10—C11—C12—C13−0.31 (13)C29—C28—C40—C354.71 (12)
C9—N2—C13—C120.02 (13)N5—C28—C40—C397.83 (13)
Ni1—N2—C13—C12−171.51 (7)C29—C28—C40—C39−171.04 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2Wi0.873 (18)2.053 (18)2.8793 (12)157.6 (16)
N3—H3B···O7ii0.878 (17)2.109 (17)2.9337 (11)156.1 (15)
N4—H4A···O60.884 (17)1.838 (17)2.7214 (11)178.1 (16)
N5—H5A···O3iii0.894 (17)1.925 (17)2.7945 (11)163.9 (16)
N5—H5B···O50.889 (17)2.046 (17)2.9096 (11)163.6 (15)
N6—H6A···O3W0.836 (18)1.863 (18)2.6903 (11)170.3 (18)
O1W—H1A···O70.83 (2)1.99 (2)2.8138 (11)171 (2)
O1W—H1B···O7iv0.861 (19)1.955 (19)2.8161 (11)178.7 (17)
O2W—H2A···O8v0.813 (19)2.067 (19)2.8717 (11)170.1 (17)
O2W—H2B···O20.79 (2)2.02 (2)2.8033 (11)177 (2)
O3W—H3C···O3vi0.79 (2)1.97 (2)2.7595 (11)169.8 (19)
O3W—H3D···O1Wvii0.856 (19)1.879 (19)2.7328 (11)175.4 (17)
C30—H30···O3iii0.931 (16)2.437 (16)3.3386 (12)163 (14)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z+1; (iii) −x+1, −y, −z; (iv) −x, −y+1, −z; (v) −x, −y, −z; (vi) x, y, z+1; (vii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2Wi0.873 (18)2.053 (18)2.8793 (12)157.6 (16)
N3—H3B···O7ii0.878 (17)2.109 (17)2.9337 (11)156.1 (15)
N4—H4A···O60.884 (17)1.838 (17)2.7214 (11)178.1 (16)
N5—H5A···O3iii0.894 (17)1.925 (17)2.7945 (11)163.9 (16)
N5—H5B···O50.889 (17)2.046 (17)2.9096 (11)163.6 (15)
N6—H6A···O3W0.836 (18)1.863 (18)2.6903 (11)170.3 (18)
O1W—H1A···O70.83 (2)1.99 (2)2.8138 (11)171 (2)
O1W—H1B···O7iv0.861 (19)1.955 (19)2.8161 (11)178.7 (17)
O2W—H2A···O8v0.813 (19)2.067 (19)2.8717 (11)170.1 (17)
O2W—H2B···O20.79 (2)2.02 (2)2.8033 (11)177 (2)
O3W—H3C···O3vi0.79 (2)1.97 (2)2.7595 (11)169.8 (19)
O3W—H3D···O1Wvii0.856 (19)1.879 (19)2.7328 (11)175.4 (17)
C30—H30···O3iii0.931 (16)2.437 (16)3.3386 (12)163 (14)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z+1; (iii) −x+1, −y, −z; (iv) −x, −y+1, −z; (v) −x, −y, −z; (vi) x, y, z+1; (vii) −x+1, −y+1, −z+1.
references
References top

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