metal-organic compounds
catena-Poly[[aqua(iminodiacetato-κ3O,N,O′)nickel(II)]-μ-4,4′-dipyridylamine-κ2N:N′]
aE-35A Holmes Hall, Michigan State University, 919 E. Shaw Lane, East Lansing, MI 48825 , USA
*Correspondence e-mail: laduca@msu.edu
In the title compound, [Ni(C4H5NO4)(C10H9N3)(H2O)]n, the NiII cations are octahedrally coordinated by an N atom donor and two O donor atoms belonging to a tridentate iminodiacetate (ida) ligand in a fac fashion, an O atom donor from an aqua ligand, and cis-disposed pyridyl N donor atoms from two 4,4′-dipyridylamine (dpa) ligands. The dpa ligands are disordered over two sets of sites in a 0.594 (7):0.406 (7) ratio. Through the bridging dpa ligands, [Ni(ida)(dpa)(H2O)]n zigzag coordination polymer chains are formed that are oriented along the b-axis direction. These chain motifs are anchored into the three-dimensional supramolecular of the title compound by means of O—H⋯O and N—H⋯O hydrogen-bonding pathways.
Keywords: nickel; coordination polymer; crystal structure.
CCDC reference: 1848969
Structure description
The dipodal tethering ligand 4,4′-dipyridylamine (dpa) has proven exceptionally useful in preparing coordination polymers with intriguing and diverse topologies (LaDuca, 2009). The title compound was prepared during synthetic attempts to prepare divalent metal coordination polymers containing both iminodiacetate (ida) and dpa ligands.
The II atom, an aqua ligand, a doubly deprotonated ida ligand and a dpa ligand. The atoms in the dpa ligand show positional disorder and were modeled successfully using refined partial occupancies [0.594 (7):0.406 (7) ratio] and two parts. The NiII atom is octahedrally coordinated (Fig. 1) with the ida ligand binding in a tridentate manner, in which O atoms of the carboxylate termini and the central imine N atom occupy three coordination sites in a fac arrangement. The bound water molecule occupies a fourth site. The remaining cis coordination sites are taken up by pyridyl N atom donors from two dpa ligands. One carboxylate O atom at each ida carboxylate terminus remains unligated.
of the title compound contains an NiThe dpa ligands act as exobidentate tethering ligands, conjoining neighboring [Ni(ida)(H2O)] coordination fragments into a one-dimensional [Ni(ida)(dpa)(H2O)]n coordination polymer ribbon (Fig. 2). These have a zigzag topology and are arranged parallel to [010], with an Ni⋯Ni through-ligand distance of 11.450 (4) Å.
The central amine moieties of the dpa ligands in one [Ni(ida)(dpa)(H2O)]n coordination polymer ribbon provide N—H⋯O hydrogen-bonding points of contact (Table 1) to unligated ida carboxylate groups in adjacent ribbon motifs. Additionally, the aqua ligands provide inter-ribbon connections (Table 1) via O—H⋯O hydrogen bonding to other unligated ida carboxylate groups. By these two distinct hydrogen-bonding pathways, the individual [Ni(ida)(dpa)(H2O)]n coordination polymer ribbons aggregate into the supramolecular three-dimensional crystal of the title compound (Fig. 3)
Synthesis and crystallization
Ni(NO3)2·6H2O (108 mg, 0.37 mmol), iminodiacetic acid (49 mg, 0.37 mol), 4,4-dipyridylamine (73 mg, 0.37 mol) and 0.75 ml of a 1.0 M NaOH solution were placed into 10 ml distilled H2O in a Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 393 K for 48 h, and then cooled slowly to 278 K. Blue block-shaped crystals of the title compound (57 mg, 41% yield based on nickel) were isolated after washing with distilled water and acetone, and drying in air.
Refinement
Crystal data, data collection and structure . The atoms of the dpa ligand are disordered in place over two sets of positions with refined occupancies in a 0.594 (7):0.406 (7) ratio. Chemically equivalent bond distances and angles were restrained to be similar using SADI and SAME commands, with an e.s.d. of 0.02 Å. SIMU commands were used to treat the thermal ellipsoids within the dpa disorder components within 2 Å with 1σ of 0.01 and σ for terminal atoms of 0.02 Å2.
details are summarized in Table 2
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Structural data
CCDC reference: 1848969
https://doi.org/10.1107/S2414314618008659/zl4025sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008659/zl4025Isup2.hkl
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: OLEX2 (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: CrystalMaker (Palmer, 2018); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[Ni(C4H5NO4)(C10H9N3)(H2O)] | F(000) = 784 |
Mr = 379.02 | Dx = 1.505 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.186 (2) Å | Cell parameters from 3842 reflections |
b = 14.541 (3) Å | θ = 2.3–25.3° |
c = 11.489 (2) Å | µ = 1.19 mm−1 |
β = 100.531 (2)° | T = 173 K |
V = 1673.0 (6) Å3 | Block, blue |
Z = 4 | 0.31 × 0.14 × 0.12 mm |
Bruker APEXII CCD diffractometer | 3823 independent reflections |
Radiation source: fine-focus sealed tube | 2480 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −13→13 |
Tmin = 0.633, Tmax = 0.745 | k = −18→18 |
15567 measured reflections | l = −14→14 |
Refinement on F2 | 526 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0833P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3823 reflections | Δρmax = 0.98 e Å−3 |
341 parameters | Δρmin = −0.34 e Å−3 |
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. |
Refinement. Hydrogen atoms bound to C and N were placed in calculated positions with a riding model with Uiso = 1.2Ueq. Hydrogen atoms bound to O were found by Fourier difference map and refined with with Uiso = 1.5Ueq. The O–H bonds were restrained to be 0.84 (2) Å using DFIX commands. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All O(H,H) groups 2. Restrained distances O5-H5A = O5-H5B 0.84 with sigma of 0.02 N2-C12 ~ N2A-C12A ~ N2-C7 ~ N2A-C7A with sigma of 0.02 N3-C10 ~ N3A-C10A ~ N3-C14 ~ N3A-C14A ~ N1-C5 ~ N1-C9 ~ N1A-C5A ~ N1A-C9A with sigma of 0.02 C12-C11 ~ C12-C13 ~ C12A-C11A ~ C12A-C13A ~ C7-C6 ~ C7-C8 ~ C7A-C6A ~ C7A-C8A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints N1 ~ C5 ~ C6 ~ C7 ~ C8 ~ C9 ~ N2 ~ N1A ~ C5A ~ C6A ~ C7A ~ C8A ~ C9A ~ N2A ~ N3 ~ C10 ~ C11 ~ C12 ~ C13 ~ C14 ~ N3A ~ C10A ~ C11A ~ C12A ~ C13A ~ C14A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 4. Same fragment restrains {N1, C5, C6, C7, C8, C9} sigma for 1-2: 0.02, 1-3: 0.04 as {N1A, C5A, C6A, C7A, C8A, C9A} {N1, C5, C6, C7, C8, C9} sigma for 1-2: 0.02, 1-3: 0.04 as {N3, C10, C11, C12, C13, C14} {N1, C5, C6, C7, C8, C9} sigma for 1-2: 0.02, 1-3: 0.04 as {N3A, C10A, C11A, C12A, C13A, C14A} 5. Others Sof(N1A)=Sof(C5A)=Sof(H5AA)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(C8A)=Sof(H8A)= Sof(C9A)=Sof(H9A)=Sof(N2A)=Sof(H2AA)=Sof(N3A)=Sof(C10A)=Sof(H10A)=Sof(C11A)= Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=1-FVAR(1) Sof(N1)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)= Sof(H9)=Sof(N2)=Sof(H2)=Sof(N3)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)= Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=FVAR(1) 6.a Ternary CH refined with riding coordinates: N4(H4) 6.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B) 6.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C8(H8), C9(H9), N2(H2), C5A(H5AA), C6A(H6A), C8A(H8A), C9A(H9A), N2A(H2AA), C10(H10), C11(H11), C13(H13), C14(H14), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A) |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.42446 (5) | 0.33031 (3) | 0.21251 (4) | 0.03457 (19) | |
O1 | 0.5512 (4) | 0.10358 (18) | 0.4044 (3) | 0.0701 (10) | |
O2 | 0.4700 (3) | 0.24245 (17) | 0.3568 (2) | 0.0461 (7) | |
O3 | 0.6004 (3) | 0.39538 (19) | 0.2771 (2) | 0.0483 (7) | |
O4 | 0.8202 (3) | 0.3844 (3) | 0.2862 (3) | 0.0738 (10) | |
O5 | 0.3899 (3) | 0.41790 (19) | 0.0653 (3) | 0.0480 (7) | |
H5A | 0.389 (5) | 0.4731 (14) | 0.076 (4) | 0.072* | |
H5B | 0.447 (4) | 0.410 (3) | 0.020 (4) | 0.072* | |
N4 | 0.5502 (3) | 0.24046 (19) | 0.1415 (3) | 0.0403 (8) | |
H4 | 0.514058 | 0.229381 | 0.055764 | 0.048* | |
C1 | 0.7034 (5) | 0.3602 (3) | 0.2478 (4) | 0.0497 (10) | |
C2 | 0.6830 (4) | 0.2840 (3) | 0.1556 (4) | 0.0540 (11) | |
H2A | 0.694940 | 0.309763 | 0.078467 | 0.065* | |
H2B | 0.752364 | 0.236389 | 0.178576 | 0.065* | |
C3 | 0.5507 (6) | 0.1544 (3) | 0.2082 (4) | 0.0589 (13) | |
H3A | 0.638836 | 0.124394 | 0.213439 | 0.071* | |
H3B | 0.482450 | 0.112505 | 0.164325 | 0.071* | |
C4 | 0.5225 (5) | 0.1680 (3) | 0.3335 (4) | 0.0508 (11) | |
N1 | 0.3086 (14) | 0.4127 (12) | 0.3028 (13) | 0.036 (2) | 0.594 (7) |
C5 | 0.3571 (17) | 0.4465 (14) | 0.4106 (15) | 0.035 (2) | 0.594 (7) |
H5 | 0.444357 | 0.428586 | 0.448093 | 0.042* | 0.594 (7) |
C6 | 0.2872 (16) | 0.5058 (13) | 0.4698 (14) | 0.037 (2) | 0.594 (7) |
H6 | 0.325579 | 0.527181 | 0.546567 | 0.044* | 0.594 (7) |
C7 | 0.1607 (18) | 0.5340 (14) | 0.4171 (10) | 0.0380 (19) | 0.594 (7) |
C8 | 0.1061 (9) | 0.4969 (6) | 0.3077 (8) | 0.0427 (18) | 0.594 (7) |
H8 | 0.017262 | 0.511208 | 0.270651 | 0.051* | 0.594 (7) |
C9 | 0.1836 (9) | 0.4390 (6) | 0.2544 (8) | 0.0437 (19) | 0.594 (7) |
H9 | 0.146575 | 0.415819 | 0.178127 | 0.052* | 0.594 (7) |
N2 | 0.0880 (13) | 0.5915 (10) | 0.4784 (14) | 0.040 (2) | 0.594 (7) |
H2 | 0.111539 | 0.589972 | 0.556019 | 0.048* | 0.594 (7) |
N1A | 0.321 (2) | 0.4209 (19) | 0.294 (2) | 0.037 (3) | 0.406 (7) |
C5A | 0.348 (3) | 0.438 (2) | 0.410 (2) | 0.038 (3) | 0.406 (7) |
H5AA | 0.423078 | 0.408253 | 0.456121 | 0.046* | 0.406 (7) |
C6A | 0.275 (2) | 0.496 (2) | 0.468 (2) | 0.037 (3) | 0.406 (7) |
H6A | 0.300689 | 0.506816 | 0.550128 | 0.044* | 0.406 (7) |
C7A | 0.162 (3) | 0.539 (2) | 0.4037 (15) | 0.040 (2) | 0.406 (7) |
C8A | 0.1327 (13) | 0.5229 (8) | 0.2833 (11) | 0.039 (2) | 0.406 (7) |
H8A | 0.058397 | 0.552148 | 0.235498 | 0.047* | 0.406 (7) |
C9A | 0.2128 (13) | 0.4638 (8) | 0.2336 (12) | 0.040 (2) | 0.406 (7) |
H9A | 0.189875 | 0.452713 | 0.150900 | 0.048* | 0.406 (7) |
N2A | 0.0984 (19) | 0.6021 (15) | 0.466 (2) | 0.040 (3) | 0.406 (7) |
H2AA | 0.139846 | 0.618221 | 0.537260 | 0.048* | 0.406 (7) |
N3 | −0.2448 (11) | 0.7591 (8) | 0.3590 (10) | 0.0416 (19) | 0.594 (7) |
C10 | −0.1977 (10) | 0.7441 (7) | 0.4736 (8) | 0.041 (2) | 0.594 (7) |
H10 | −0.243491 | 0.770769 | 0.530282 | 0.049* | 0.594 (7) |
C11 | −0.0861 (9) | 0.6921 (6) | 0.5135 (8) | 0.0417 (19) | 0.594 (7) |
H11 | −0.056494 | 0.684199 | 0.596263 | 0.050* | 0.594 (7) |
C12 | −0.0165 (12) | 0.6511 (10) | 0.4354 (10) | 0.0403 (16) | 0.594 (7) |
C13 | −0.0612 (7) | 0.6711 (5) | 0.3157 (6) | 0.0472 (16) | 0.594 (7) |
H13 | −0.014160 | 0.648297 | 0.257621 | 0.057* | 0.594 (7) |
C14 | −0.1723 (7) | 0.7233 (5) | 0.2831 (6) | 0.0500 (16) | 0.594 (7) |
H14 | −0.200814 | 0.735312 | 0.201164 | 0.060* | 0.594 (7) |
N3A | −0.2610 (16) | 0.7430 (11) | 0.3535 (15) | 0.043 (2) | 0.406 (7) |
C10A | −0.1774 (15) | 0.7604 (11) | 0.4548 (13) | 0.043 (3) | 0.406 (7) |
H10A | −0.199719 | 0.808832 | 0.503081 | 0.051* | 0.406 (7) |
C11A | −0.0608 (14) | 0.7126 (9) | 0.4939 (12) | 0.044 (2) | 0.406 (7) |
H11A | −0.005251 | 0.727873 | 0.567026 | 0.053* | 0.406 (7) |
C12A | −0.0261 (18) | 0.6417 (14) | 0.4245 (16) | 0.042 (2) | 0.406 (7) |
C13A | −0.1218 (10) | 0.6158 (7) | 0.3269 (9) | 0.048 (2) | 0.406 (7) |
H13A | −0.109876 | 0.561189 | 0.284776 | 0.057* | 0.406 (7) |
C14A | −0.2321 (10) | 0.6688 (7) | 0.2921 (9) | 0.046 (2) | 0.406 (7) |
H14A | −0.291507 | 0.652863 | 0.221304 | 0.055* | 0.406 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0394 (3) | 0.0317 (3) | 0.0326 (3) | −0.00311 (19) | 0.0064 (2) | −0.00321 (18) |
O1 | 0.134 (3) | 0.0361 (15) | 0.0441 (17) | 0.0179 (17) | 0.0256 (18) | 0.0099 (13) |
O2 | 0.072 (2) | 0.0348 (14) | 0.0343 (14) | 0.0032 (13) | 0.0165 (13) | −0.0015 (11) |
O3 | 0.0441 (17) | 0.0523 (17) | 0.0486 (17) | −0.0074 (13) | 0.0091 (13) | −0.0146 (13) |
O4 | 0.0414 (19) | 0.112 (3) | 0.068 (2) | −0.0160 (19) | 0.0092 (16) | −0.019 (2) |
O5 | 0.064 (2) | 0.0358 (14) | 0.0430 (16) | −0.0068 (14) | 0.0070 (13) | 0.0013 (13) |
N4 | 0.058 (2) | 0.0352 (16) | 0.0286 (15) | 0.0038 (15) | 0.0091 (14) | −0.0023 (12) |
C1 | 0.046 (3) | 0.064 (3) | 0.039 (2) | −0.003 (2) | 0.0086 (19) | −0.0007 (19) |
C2 | 0.049 (3) | 0.067 (3) | 0.047 (2) | 0.007 (2) | 0.011 (2) | −0.003 (2) |
C3 | 0.106 (4) | 0.038 (2) | 0.038 (2) | 0.014 (2) | 0.027 (2) | 0.0018 (17) |
C4 | 0.084 (3) | 0.037 (2) | 0.034 (2) | −0.002 (2) | 0.018 (2) | −0.0020 (17) |
N1 | 0.035 (3) | 0.037 (4) | 0.037 (3) | −0.002 (3) | 0.006 (3) | −0.002 (3) |
C5 | 0.031 (3) | 0.035 (4) | 0.038 (3) | −0.003 (3) | 0.005 (3) | −0.001 (3) |
C6 | 0.034 (4) | 0.041 (4) | 0.036 (3) | −0.005 (3) | 0.007 (3) | −0.001 (3) |
C7 | 0.033 (3) | 0.040 (3) | 0.042 (3) | 0.000 (3) | 0.007 (3) | 0.002 (3) |
C8 | 0.034 (3) | 0.045 (4) | 0.046 (4) | −0.002 (3) | 0.001 (3) | 0.002 (3) |
C9 | 0.040 (4) | 0.044 (4) | 0.043 (4) | −0.005 (3) | −0.002 (3) | −0.001 (3) |
N2 | 0.033 (3) | 0.048 (4) | 0.041 (3) | 0.008 (3) | 0.013 (3) | 0.004 (3) |
N1A | 0.036 (4) | 0.037 (4) | 0.037 (4) | −0.001 (4) | 0.003 (4) | −0.005 (4) |
C5A | 0.036 (4) | 0.037 (5) | 0.041 (4) | 0.000 (4) | 0.005 (4) | 0.000 (4) |
C6A | 0.034 (4) | 0.041 (5) | 0.036 (4) | −0.004 (4) | 0.007 (4) | 0.001 (4) |
C7A | 0.035 (3) | 0.040 (4) | 0.044 (4) | 0.002 (3) | 0.008 (3) | 0.002 (4) |
C8A | 0.035 (4) | 0.043 (4) | 0.037 (4) | 0.004 (4) | 0.003 (3) | 0.006 (4) |
C9A | 0.040 (4) | 0.043 (5) | 0.035 (4) | 0.001 (4) | 0.005 (4) | 0.002 (4) |
N2A | 0.037 (4) | 0.043 (4) | 0.041 (4) | 0.004 (4) | 0.011 (4) | 0.004 (4) |
N3 | 0.042 (3) | 0.043 (4) | 0.040 (3) | 0.012 (3) | 0.008 (3) | 0.007 (3) |
C10 | 0.043 (4) | 0.043 (4) | 0.039 (3) | 0.002 (3) | 0.013 (3) | 0.000 (3) |
C11 | 0.041 (4) | 0.045 (4) | 0.041 (3) | 0.005 (3) | 0.011 (3) | 0.007 (3) |
C12 | 0.033 (3) | 0.047 (3) | 0.041 (3) | 0.005 (3) | 0.009 (3) | 0.003 (3) |
C13 | 0.044 (3) | 0.059 (3) | 0.042 (3) | 0.016 (3) | 0.019 (3) | 0.005 (3) |
C14 | 0.048 (3) | 0.057 (4) | 0.046 (3) | 0.013 (3) | 0.011 (3) | 0.011 (3) |
N3A | 0.042 (4) | 0.045 (5) | 0.040 (4) | 0.010 (4) | 0.005 (3) | 0.003 (3) |
C10A | 0.046 (4) | 0.041 (4) | 0.042 (4) | 0.009 (4) | 0.011 (4) | −0.004 (4) |
C11A | 0.040 (4) | 0.050 (5) | 0.043 (4) | 0.005 (4) | 0.008 (4) | 0.002 (4) |
C12A | 0.037 (4) | 0.047 (4) | 0.045 (4) | 0.010 (3) | 0.014 (3) | 0.003 (3) |
C13A | 0.044 (4) | 0.052 (4) | 0.048 (4) | 0.013 (3) | 0.012 (3) | −0.007 (3) |
C14A | 0.043 (4) | 0.052 (4) | 0.043 (4) | 0.013 (4) | 0.006 (3) | −0.003 (3) |
Ni1—O2 | 2.078 (3) | N2—C12 | 1.391 (10) |
Ni1—O3 | 2.043 (3) | N1A—C5A | 1.339 (13) |
Ni1—O5 | 2.095 (3) | N1A—C9A | 1.343 (12) |
Ni1—N4 | 2.096 (3) | C5A—H5AA | 0.9500 |
Ni1—N1 | 2.086 (14) | C5A—C6A | 1.371 (12) |
Ni1—N1A | 2.02 (2) | C6A—H6A | 0.9500 |
Ni1—N3i | 2.132 (10) | C6A—C7A | 1.390 (12) |
Ni1—N3Ai | 2.121 (14) | C7A—C8A | 1.381 (12) |
O1—C4 | 1.241 (5) | C7A—N2A | 1.400 (13) |
O2—C4 | 1.257 (5) | C8A—H8A | 0.9500 |
O3—C1 | 1.267 (5) | C8A—C9A | 1.378 (11) |
O4—C1 | 1.242 (5) | C9A—H9A | 0.9500 |
O5—H5A | 0.812 (19) | N2A—H2AA | 0.8800 |
O5—H5B | 0.856 (19) | N2A—C12A | 1.395 (13) |
N4—H4 | 1.0000 | N3—C10 | 1.334 (10) |
N4—C2 | 1.475 (5) | N3—C14 | 1.347 (10) |
N4—C3 | 1.467 (5) | C10—H10 | 0.9500 |
C1—C2 | 1.520 (6) | C10—C11 | 1.372 (9) |
C2—H2A | 0.9900 | C11—H11 | 0.9500 |
C2—H2B | 0.9900 | C11—C12 | 1.378 (10) |
C3—H3A | 0.9900 | C12—C13 | 1.397 (11) |
C3—H3B | 0.9900 | C13—H13 | 0.9500 |
C3—C4 | 1.531 (6) | C13—C14 | 1.357 (8) |
N1—C5 | 1.341 (10) | C14—H14 | 0.9500 |
N1—C9 | 1.348 (9) | N3A—C10A | 1.334 (12) |
C5—H5 | 0.9500 | N3A—C14A | 1.351 (12) |
C5—C6 | 1.374 (9) | C10A—H10A | 0.9500 |
C6—H6 | 0.9500 | C10A—C11A | 1.378 (12) |
C6—C7 | 1.382 (10) | C11A—H11A | 0.9500 |
C7—C8 | 1.388 (10) | C11A—C12A | 1.388 (12) |
C7—N2 | 1.391 (9) | C12A—C13A | 1.395 (12) |
C8—H8 | 0.9500 | C13A—H13A | 0.9500 |
C8—C9 | 1.373 (9) | C13A—C14A | 1.360 (10) |
C9—H9 | 0.9500 | C14A—H14A | 0.9500 |
N2—H2 | 0.8800 | ||
O2—Ni1—O5 | 176.65 (12) | C8—C7—N2 | 122.0 (13) |
O2—Ni1—N4 | 82.18 (11) | C7—C8—H8 | 120.8 |
O2—Ni1—N1 | 91.2 (4) | C9—C8—C7 | 118.4 (8) |
O2—Ni1—N3i | 93.4 (3) | C9—C8—H8 | 120.8 |
O2—Ni1—N3Ai | 87.9 (4) | N1—C9—C8 | 124.5 (8) |
O3—Ni1—O2 | 86.66 (11) | N1—C9—H9 | 117.7 |
O3—Ni1—O5 | 91.05 (11) | C8—C9—H9 | 117.7 |
O3—Ni1—N4 | 82.64 (12) | C7—N2—H2 | 115.2 |
O3—Ni1—N1 | 95.3 (5) | C7—N2—C12 | 129.6 (13) |
O3—Ni1—N3i | 177.8 (4) | C12—N2—H2 | 115.2 |
O3—Ni1—N3Ai | 170.6 (5) | C5A—N1A—Ni1 | 123.6 (14) |
O5—Ni1—N4 | 95.11 (12) | C5A—N1A—C9A | 115.3 (14) |
O5—Ni1—N3i | 88.8 (3) | C9A—N1A—Ni1 | 120.9 (13) |
O5—Ni1—N3Ai | 94.0 (4) | N1A—C5A—H5AA | 117.8 |
N4—Ni1—N3i | 95.2 (4) | N1A—C5A—C6A | 124.3 (16) |
N4—Ni1—N3Ai | 89.0 (6) | C6A—C5A—H5AA | 117.8 |
N1—Ni1—O5 | 91.5 (4) | C5A—C6A—H6A | 120.3 |
N1—Ni1—N4 | 173.1 (4) | C5A—C6A—C7A | 119.3 (15) |
N1—Ni1—N3i | 87.0 (6) | C7A—C6A—H6A | 120.3 |
N1—Ni1—N3Ai | 92.5 (8) | C6A—C7A—N2A | 116.1 (16) |
N1A—Ni1—O2 | 95.2 (7) | C8A—C7A—C6A | 117.6 (13) |
N1A—Ni1—O3 | 91.6 (8) | C8A—C7A—N2A | 125.9 (18) |
N1A—Ni1—O5 | 87.2 (7) | C7A—C8A—H8A | 120.6 |
N1A—Ni1—N4 | 173.8 (7) | C9A—C8A—C7A | 118.8 (11) |
N1A—Ni1—N3Ai | 96.5 (10) | C9A—C8A—H8A | 120.6 |
C4—O2—Ni1 | 113.6 (2) | N1A—C9A—C8A | 124.7 (12) |
C1—O3—Ni1 | 115.5 (3) | N1A—C9A—H9A | 117.7 |
Ni1—O5—H5A | 119 (3) | C8A—C9A—H9A | 117.7 |
Ni1—O5—H5B | 112 (3) | C7A—N2A—H2AA | 117.5 |
H5A—O5—H5B | 105 (5) | C12A—N2A—C7A | 125 (2) |
Ni1—N4—H4 | 110.0 | C12A—N2A—H2AA | 117.5 |
C2—N4—Ni1 | 107.6 (2) | C10—N3—Ni1ii | 126.0 (8) |
C2—N4—H4 | 110.0 | C10—N3—C14 | 115.8 (9) |
C3—N4—Ni1 | 105.8 (2) | C14—N3—Ni1ii | 118.2 (7) |
C3—N4—H4 | 110.0 | N3—C10—H10 | 118.4 |
C3—N4—C2 | 113.2 (4) | N3—C10—C11 | 123.1 (9) |
O3—C1—C2 | 117.7 (4) | C11—C10—H10 | 118.4 |
O4—C1—O3 | 125.3 (4) | C10—C11—H11 | 119.5 |
O4—C1—C2 | 117.0 (4) | C10—C11—C12 | 120.9 (8) |
N4—C2—C1 | 113.3 (3) | C12—C11—H11 | 119.5 |
N4—C2—H2A | 108.9 | N2—C12—C13 | 124.8 (11) |
N4—C2—H2B | 108.9 | C11—C12—N2 | 119.3 (11) |
C1—C2—H2A | 108.9 | C11—C12—C13 | 115.9 (8) |
C1—C2—H2B | 108.9 | C12—C13—H13 | 120.2 |
H2A—C2—H2B | 107.7 | C14—C13—C12 | 119.6 (7) |
N4—C3—H3A | 108.9 | C14—C13—H13 | 120.2 |
N4—C3—H3B | 108.9 | N3—C14—C13 | 124.5 (7) |
N4—C3—C4 | 113.4 (3) | N3—C14—H14 | 117.8 |
H3A—C3—H3B | 107.7 | C13—C14—H14 | 117.8 |
C4—C3—H3A | 108.9 | C10A—N3A—C14A | 116.2 (13) |
C4—C3—H3B | 108.9 | N3A—C10A—H10A | 117.9 |
O1—C4—O2 | 124.6 (4) | N3A—C10A—C11A | 124.3 (13) |
O1—C4—C3 | 117.2 (4) | C11A—C10A—H10A | 117.9 |
O2—C4—C3 | 118.2 (4) | C10A—C11A—H11A | 120.6 |
C5—N1—Ni1 | 121.6 (10) | C10A—C11A—C12A | 118.8 (11) |
C5—N1—C9 | 116.0 (10) | C12A—C11A—H11A | 120.6 |
C9—N1—Ni1 | 122.4 (9) | N2A—C12A—C13A | 128.5 (15) |
N1—C5—H5 | 118.3 | C11A—C12A—N2A | 114.8 (14) |
N1—C5—C6 | 123.4 (11) | C11A—C12A—C13A | 116.6 (11) |
C6—C5—H5 | 118.3 | C12A—C13A—H13A | 120.0 |
C5—C6—H6 | 120.1 | C14A—C13A—C12A | 120.1 (10) |
C5—C6—C7 | 119.8 (10) | C14A—C13A—H13A | 120.0 |
C7—C6—H6 | 120.1 | N3A—C14A—C13A | 123.1 (10) |
C6—C7—C8 | 117.9 (9) | N3A—C14A—H14A | 118.5 |
C6—C7—N2 | 119.8 (12) | C13A—C14A—H14A | 118.5 |
Ni1—O2—C4—O1 | −175.9 (4) | C9—N1—C5—C6 | −1 (3) |
Ni1—O2—C4—C3 | 2.7 (5) | N2—C7—C8—C9 | −178.4 (14) |
Ni1—O3—C1—O4 | −173.2 (4) | N2—C12—C13—C14 | 173.6 (14) |
Ni1—O3—C1—C2 | 8.6 (5) | N1A—C5A—C6A—C7A | 2 (5) |
Ni1—N4—C2—C1 | 18.7 (4) | C5A—N1A—C9A—C8A | 1 (4) |
Ni1—N4—C3—C4 | −26.9 (5) | C5A—C6A—C7A—C8A | −2 (5) |
Ni1—N1—C5—C6 | 175.7 (14) | C5A—C6A—C7A—N2A | −175 (3) |
Ni1—N1—C9—C8 | −176.5 (8) | C6A—C7A—C8A—C9A | 2 (4) |
Ni1—N1A—C5A—C6A | −177 (2) | C6A—C7A—N2A—C12A | −170 (3) |
Ni1—N1A—C9A—C8A | 176.5 (12) | C7A—C8A—C9A—N1A | −1 (3) |
Ni1ii—N3—C10—C11 | 175.2 (7) | C7A—N2A—C12A—C11A | −171 (2) |
Ni1ii—N3—C14—C13 | −175.3 (7) | C7A—N2A—C12A—C13A | 13 (5) |
Ni1ii—N3A—C10A—C11A | −171.5 (11) | C8A—C7A—N2A—C12A | 18 (5) |
Ni1ii—N3A—C14A—C13A | 174.3 (11) | C9A—N1A—C5A—C6A | −1 (5) |
O3—C1—C2—N4 | −19.1 (6) | N2A—C7A—C8A—C9A | 174 (2) |
O4—C1—C2—N4 | 162.5 (4) | N2A—C12A—C13A—C14A | −173 (2) |
N4—C3—C4—O1 | −163.7 (4) | N3—C10—C11—C12 | −0.6 (17) |
N4—C3—C4—O2 | 17.6 (6) | C10—N3—C14—C13 | 3.0 (17) |
C2—N4—C3—C4 | 90.7 (5) | C10—C11—C12—N2 | −173.7 (13) |
C3—N4—C2—C1 | −97.9 (4) | C10—C11—C12—C13 | 4.1 (18) |
N1—C5—C6—C7 | −1 (3) | C11—C12—C13—C14 | −4.1 (18) |
C5—N1—C9—C8 | 0 (3) | C12—C13—C14—N3 | 0.5 (16) |
C5—C6—C7—C8 | 3 (3) | C14—N3—C10—C11 | −3.0 (17) |
C5—C6—C7—N2 | 177.8 (17) | N3A—C10A—C11A—C12A | 0 (3) |
C6—C7—C8—C9 | −4 (3) | C10A—N3A—C14A—C13A | −3 (3) |
C6—C7—N2—C12 | 157 (2) | C10A—C11A—C12A—N2A | 175.1 (19) |
C7—C8—C9—N1 | 2.4 (17) | C10A—C11A—C12A—C13A | −8 (3) |
C7—N2—C12—C11 | 171.1 (16) | C11A—C12A—C13A—C14A | 11 (3) |
C7—N2—C12—C13 | −7 (3) | C12A—C13A—C14A—N3A | −6 (2) |
C8—C7—N2—C12 | −29 (3) | C14A—N3A—C10A—C11A | 5 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O1iii | 0.81 (2) | 1.99 (2) | 2.774 (4) | 161 (5) |
O5—H5B···O1iv | 0.86 (2) | 1.86 (2) | 2.706 (5) | 172 (5) |
N4—H4···O2iv | 1.00 | 2.28 | 3.233 (4) | 158 |
C2—H2A···O1iv | 0.99 | 2.58 | 3.374 (6) | 137 |
C6—H6···O3v | 0.95 | 2.32 | 3.259 (14) | 170 |
C9—H9···N3i | 0.95 | 2.56 | 3.037 (16) | 112 |
N2—H2···O4v | 0.88 | 1.86 | 2.718 (16) | 166 |
C6A—H6A···O3v | 0.95 | 2.50 | 3.37 (2) | 152 |
C9A—H9A···O5 | 0.95 | 2.47 | 2.952 (13) | 111 |
N2A—H2AA···O4v | 0.88 | 1.99 | 2.82 (2) | 156 |
C10A—H10A···O5ii | 0.95 | 2.52 | 3.131 (15) | 123 |
C14A—H14A···O2ii | 0.95 | 2.28 | 2.904 (9) | 122 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y+1, −z+1. |
Acknowledgements
We thank Mr Andrew R. LaDuca for preparing the molecular graphics.
Funding information
Funding for this research was provided by: Michigan State University, Honors College.
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