metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

Di­aqua­bis­­[N,N′-(ethane-1,2-di­yl)bis­­(isonico­tin­amide)-κN]bis­­(hydrogen phthalato-κO)nickel(II) hexa­hydrate

CROSSMARK_Color_square_no_text.svg

aE-35A Holmes Hall, Michigan State University, 919 E. Shaw Lane, East Lansing, MI 48825, USA
*Correspondence e-mail: laduca@msu.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 6 July 2016; accepted 18 July 2016; online 22 July 2016)

In the title solvated coordination complex, [Ni(C8H5O4)2(C14H14N4O2)2(H2O)2]·6H2O, the NiII cation is octa­hedrally coordinated by trans carboxyl­ate O-atom donors from two crystallographically distinct monodentate hydrogen phthalate (Hpht) ligands, two trans aqua ligands, and trans pyridyl N-atom donors from two crystallographically distinct N,N′-(ethane-1,2-di­yl)bis(isonicotinamide) (ebin) ligands. Extensive O—H⋯O and O—H⋯N hydrogen-bonding patterns involving the water mol­ecules of crystallization anchor neighboring coordination complexes into a three-dimensional network.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title coordination complex was isolated during an attempt to prepare a nickel phthalate (pht) coordination polymer containing N,N′-(ethane-1,2-di­yl)bis­(iso­nico­tin­amide) (ebin) co-ligands. Nickel phthalate coordination polymers have displayed different structural topologies and property behavior depending on the nature of the neutral nitro­gen-base co-ligand. For example, {[(pht)2Ni(dpa)2Ni(H2O)4].H2O}n (dpa = 4,4′-di­pyridyl­amine) displays a chain structure (Braverman et al., 2007[Braverman, M. A., Supkowski, R. M. & LaDuca, R. L. (2007). Inorg. Chim. Acta, 360, 2353-2362.]). The compound [Ni(pht)(4-meim)2(H2O]n (4-meim = 4-methyl­imidazole), likewise with a one-dimensional structure, shows a negative influence on protease enzyme synthesis in fungal cultures in vivo (Filippova et al., 2010[Filippova, I. G., Gherco, O. A., Simonov, Y. A., Deseatnic-Ciloci, A. A., Clapco, S. F., Tiurina, J. P. & Baca, S. G. (2010). Polyhedron, 29, 1102-1108.]). [Ni(pht)(1,4-bib)]n [1,4-bib = 1,4-bis­(imidazol-l-ylmeth­yl)benzene] exhibits a two-dimensional 63 herringbone topology and has non-linear optical behavior (Zhao et al., 2015[Zhao, N., Deng, Y., Liu, P., An, C. X., Wang, T. X. & Lian, Z. X. (2015). Polyhedron, 85, 607-614.]). [Ni(pht)(bbi)]n [bbi = 1,1′-(1,4-butanedi­yl)bis­(imidazole)] manifests a 4-connected three-dimensional 658 cds topology (Qi et al., 2008[Qi, Y., Luo, F., Che, Y. & Zheng, J. (2008). Cryst. Growth Des. 8, 606-611.]).

The asymmetric unit of the title compound contains one NiII cation, two Hpht ligands, two aqua ligands, two ebin ligands, thus forming the coordination complex [Ni(Hpht)2(ebin)2(H2O)2] (Fig. 1[link]). Six water mol­ecules of crystallization also reside in the asymmetric unit. The NiII cation is octa­hedrally coordinated by trans carboxyl­ate O atom donors from two monodentate hydrogenphthalato (Hpht) ligands, two trans aqua ligands, and trans pyridyl N atom donors from two N,N′-(ethane-1,2-di­yl)bis­(isonicotinamide) (ebin) ligands. The two ebin ligands have an anti-conformation at their central (ethane-1,2-di­yl)di­amine moieties [N—C—C—N torsion angles = 179.68 (19) and 179.87 (19)°]. Bond lengths (Table 1[link]) and angles confirm an octa­hedral coordination environment for the NiII atom.

Table 1
Selected bond lengths (Å)

Ni1—O13 2.0643 (15) Ni1—O9 2.1274 (15)
Ni1—O14 2.0563 (15) Ni1—N1 2.1105 (18)
Ni1—O5 2.1045 (15) Ni1—N5 2.1146 (18)
[Figure 1]
Figure 1
The coordination complex of the title compound, showing octa­hedral coordination at the NiII cation. Displacement ellipsoids are drawn at the 50% probability level and H atom positions are shown as gray sticks.

Within the complex, intra­molecular O—H⋯O hydrogen bonding is observed between the aqua ligands and the unbound O atoms belonging to the ligated and deprotonated Hpht carboxyl­ate groups (Table 2[link]). Supra­molecular layers parallel to (011) are constructed by O—H⋯N hydrogen bonding between unligated and protonated Hpht carboxyl­ate groups and unligated ebin pyridyl N atoms (Fig. 2[link]). Water mol­ecule pairs are anchored to the supra­molecular layers by N—H⋯O hydrogen-bonding acceptance from ebin amide N—H groups, and O—H⋯O hydrogen-bonding donation to ebin amide C=O groups. Adjacent supra­molecular layers aggregate and stack in an ABAB pattern along [010] (Fig. 3[link]) by means of N—H⋯O hydrogen bonding from ebin amide N—H groups to isolated water mol­ecules of crystallization, which in turn provide O—H⋯O hydrogen-bonding donation to ligated Hpht carboxyl­ate O atoms (Table 2[link]).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O8—H8⋯N4i 0.84 1.78 2.609 (3) 171
O11—H11⋯N8ii 0.84 1.82 2.660 (3) 176
O13—H13A⋯O2W 0.88 1.90 2.706 (2) 150
O13—H13B⋯O12 0.88 1.94 2.733 (2) 149
O14—H14B⋯O6 0.88 1.87 2.668 (2) 149
N2—H2⋯O1Wiii 0.88 2.02 2.887 (3) 166
N3—H3⋯O3Wii 0.88 2.02 2.874 (3) 164
N6—H6⋯O6Wiv 0.88 1.99 2.844 (3) 164
O1W—H1WA⋯O12v 0.87 1.93 2.801 (2) 177
O1W—H1WB⋯O5 0.87 2.12 2.967 (2) 165
O2W—H2WA⋯O12v 0.87 2.02 2.840 (2) 158
O2W—H2WB⋯O2iii 0.87 1.90 2.757 (2) 169
O3W—H3WA⋯O5Wiv 0.87 1.98 2.849 (3) 173
O3W—H3WB⋯O3 0.87 1.91 2.777 (2) 175
O4W—H4WA⋯O4 0.87 1.96 2.800 (2) 161
O4W—H4WB⋯O14iv 0.87 1.86 2.706 (2) 165
O5W—H5WA⋯O10 0.87 1.98 2.821 (3) 162
O5W—H5WB⋯O1vi 0.87 1.92 2.776 (2) 169
O6W—H6WA⋯O6vii 0.87 1.90 2.770 (2) 178
O6W—H6WB⋯O9 0.87 2.12 2.977 (2) 167
Symmetry codes: (i) x-1, y+1, z-1; (ii) x+1, y-1, z+1; (iii) -x+2, -y+1, -z+1; (iv) -x, -y+2, -z+1; (v) -x+1, -y+1, -z+1; (vi) -x+1, -y+1, -z+2; (vii) -x+1, -y+2, -z+1.
[Figure 2]
Figure 2
Supra­molecular layer parallel to (011) in the title compound formed by O—H⋯N hydrogen bonding inter­actions between unligated Hpht carboxyl­ate groups and unligated ebin pyridyl nitro­gen atoms. H-atom positions were omitted for clarity.
[Figure 3]
Figure 3
ABAB stacking pattern of supra­molecular layer motifs in the title compound, mediated by N—H⋯O and O–H⋯O hydrogen bonding patterns involving the water mol­ecules of crystallization situated in the inter­lamellar regions. H-atom positions were omitted for clarity.

Synthesis and crystallization

Ni(NO3)2·6H2O (108 mg, 0.37 mmol), phthalic acid (61 mg, 0.37 mol), ebin (100 mg, 0.37 mol) and 0.75 ml of a 1.0 M NaOH solution were placed into 10 ml distilled water 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. Green crystals of the title compound (106 mg, 53% yield based on ebin) were isolated after washing with distilled water and acetone, and drying in air.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link].

Table 3
Experimental details

Crystal data
Chemical formula [Ni(C8H5O4)2(C14H14N4O2)2(H2O)2]·6H2O
Mr 1073.64
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 173
a, b, c (Å) 10.2857 (12), 14.3250 (17), 17.794 (2)
α, β, γ (°) 71.528 (1), 79.919 (1), 72.784 (1)
V3) 2365.7 (5)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.50
Crystal size (mm) 0.27 × 0.21 × 0.10
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.711, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections 36698, 8669, 6860
Rint 0.039
(sin θ/λ)max−1) 0.603
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.115, 1.05
No. of reflections 8669
No. of parameters 680
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.64, −0.64
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), olex2.solve (Bourhis et al., 2015[Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59-75.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Crystal Maker (Palmer, 2013[Palmer, D. (2013). Crystal Maker. Crystal Maker Software, Bicester, England.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and OLEX2 (Dolomanov et al., 2009); molecular graphics: Crystal Maker (Palmer, 2013); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Diaquabis[N,N'-(ethane-1,2-diyl)bis(isonicotinamide)-κN]bis(hydrogen phthalato-κO)nickel(II) hexahydrate top
Crystal data top
[Ni(C8H5O4)2(C14H14N4O2)2(H2O)2]·6H2OZ = 2
Mr = 1073.64F(000) = 1124
Triclinic, P1Dx = 1.507 Mg m3
a = 10.2857 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.3250 (17) ÅCell parameters from 9906 reflections
c = 17.794 (2) Åθ = 2.3–25.3°
α = 71.528 (1)°µ = 0.50 mm1
β = 79.919 (1)°T = 173 K
γ = 72.784 (1)°Block, green
V = 2365.7 (5) Å30.27 × 0.21 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
8669 independent reflections
Radiation source: sealed tube6860 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 836.6 pixels mm-1θmax = 25.4°, θmin = 1.6°
φ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 1717
Tmin = 0.711, Tmax = 0.745l = 2121
36698 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0552P)2 + 1.3935P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
8669 reflectionsΔρmax = 0.64 e Å3
680 parametersΔρmin = 0.64 e Å3
0 restraints
Special details top

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) top
xyzUiso*/Ueq
Ni10.49745 (3)0.74721 (2)0.50914 (2)0.01646 (10)
O10.82860 (17)0.45611 (14)0.85737 (10)0.0331 (4)
O21.51830 (17)0.27370 (13)0.80397 (10)0.0325 (4)
O30.19602 (17)1.05743 (14)0.15603 (10)0.0352 (5)
O40.50372 (17)1.22484 (13)0.17927 (10)0.0318 (4)
O50.67444 (15)0.75127 (11)0.42961 (9)0.0183 (3)
O60.70332 (17)0.90064 (12)0.42718 (11)0.0308 (4)
O70.69349 (17)0.91897 (13)0.25517 (10)0.0330 (4)
O80.86509 (18)0.92196 (16)0.15992 (10)0.0391 (5)
H80.80150.95720.13100.059*
O90.32138 (15)0.74082 (11)0.59165 (9)0.0189 (3)
O100.0904 (2)0.57849 (15)0.86281 (10)0.0404 (5)
O110.27474 (18)0.57567 (14)0.77595 (10)0.0351 (4)
H110.31380.53790.81670.053*
O120.29879 (17)0.58649 (12)0.60231 (10)0.0290 (4)
O130.50251 (16)0.61563 (11)0.48298 (9)0.0215 (4)
H13A0.48710.62950.43280.032*
H13B0.43900.58740.51370.032*
O140.49020 (16)0.87908 (11)0.53467 (9)0.0215 (4)
H14A0.40990.92300.52530.032*
H14B0.55440.90710.50470.032*
N10.62369 (18)0.65432 (14)0.60069 (11)0.0189 (4)
N21.01031 (19)0.41926 (14)0.77027 (11)0.0229 (4)
H21.04580.43050.72050.028*
N31.3188 (2)0.24783 (15)0.86972 (12)0.0257 (5)
H31.27650.21630.91350.031*
N41.6880 (2)0.03666 (17)1.05794 (13)0.0340 (5)
N50.37401 (18)0.83994 (14)0.41590 (11)0.0184 (4)
N60.00097 (19)1.07507 (14)0.23624 (11)0.0215 (4)
H60.04091.05840.28420.026*
N70.2954 (2)1.24525 (15)0.12505 (12)0.0266 (5)
H70.24731.27550.08350.032*
N80.6137 (2)1.45381 (16)0.09158 (13)0.0354 (5)
C10.7449 (2)0.59222 (17)0.58465 (14)0.0222 (5)
H10.77070.58980.53120.027*
C20.8340 (2)0.53179 (17)0.64121 (13)0.0214 (5)
H2A0.91980.49080.62640.026*
C30.7964 (2)0.53183 (16)0.72011 (13)0.0194 (5)
C40.6697 (2)0.59523 (17)0.73731 (14)0.0225 (5)
H40.64000.59750.79050.027*
C50.5880 (2)0.65450 (17)0.67687 (13)0.0204 (5)
H50.50250.69740.68970.025*
C60.8811 (2)0.46600 (17)0.78795 (14)0.0219 (5)
C71.0928 (2)0.34900 (18)0.83455 (14)0.0246 (5)
H7A1.05710.28800.85850.030*
H7B1.08580.38250.87650.030*
C81.2404 (2)0.31724 (18)0.80369 (14)0.0247 (5)
H8A1.24820.28290.76220.030*
H8B1.27670.37800.77970.030*
C91.4533 (2)0.23228 (18)0.86387 (14)0.0235 (5)
C101.5292 (2)0.16153 (17)0.93421 (14)0.0244 (5)
C111.6701 (3)0.1322 (2)0.92201 (16)0.0360 (7)
H11A1.71500.15480.87080.043*
C121.7447 (3)0.0699 (2)0.98459 (16)0.0413 (7)
H121.84140.04960.97510.050*
C131.5523 (3)0.06410 (19)1.07036 (15)0.0289 (6)
H131.51060.04031.12230.035*
C141.4696 (3)0.12619 (18)1.01016 (14)0.0269 (6)
H141.37300.14421.02100.032*
C150.4203 (2)0.84744 (17)0.33952 (14)0.0211 (5)
H150.50860.80700.32780.025*
C160.3449 (2)0.91165 (18)0.27709 (14)0.0230 (5)
H160.38290.91680.22370.028*
C170.2134 (2)0.96857 (17)0.29281 (13)0.0197 (5)
C180.1646 (2)0.95989 (17)0.37186 (13)0.0209 (5)
H180.07490.99690.38530.025*
C190.2478 (2)0.89696 (17)0.43065 (14)0.0222 (5)
H190.21420.89360.48440.027*
C200.1352 (2)1.03773 (17)0.22313 (14)0.0227 (5)
C210.0749 (2)1.14415 (18)0.16946 (14)0.0240 (5)
H21A0.06151.11010.12720.029*
H21B0.03921.20530.14730.029*
C220.2266 (2)1.17618 (19)0.19489 (14)0.0258 (5)
H22A0.26371.11560.21650.031*
H22B0.24131.21100.23680.031*
C230.4296 (2)1.26325 (17)0.12320 (14)0.0235 (5)
C240.4899 (2)1.33226 (18)0.04703 (15)0.0254 (5)
C250.4141 (3)1.3655 (2)0.02330 (15)0.0330 (6)
H250.31711.34720.02540.040*
C260.4795 (3)1.4256 (2)0.09107 (16)0.0382 (7)
H260.42531.44720.13900.046*
C270.6881 (3)1.4218 (2)0.02409 (16)0.0344 (6)
H270.78481.44140.02410.041*
C280.6311 (3)1.3610 (2)0.04669 (16)0.0327 (6)
H280.68781.33970.09360.039*
C290.7415 (2)0.81806 (17)0.41064 (13)0.0196 (5)
C300.8842 (2)0.78887 (16)0.37059 (14)0.0190 (5)
C310.9853 (2)0.72325 (18)0.41893 (15)0.0243 (5)
H310.96160.69680.47410.029*
C321.1202 (2)0.69546 (18)0.38840 (16)0.0283 (6)
H321.18830.65190.42270.034*
C331.1552 (2)0.73139 (19)0.30775 (16)0.0285 (6)
H331.24720.71220.28630.034*
C341.0555 (2)0.79525 (18)0.25885 (15)0.0265 (5)
H341.07960.81930.20340.032*
C350.9196 (2)0.82543 (17)0.28905 (14)0.0213 (5)
C360.8142 (2)0.89364 (18)0.23390 (14)0.0232 (5)
C370.2565 (2)0.67276 (17)0.61349 (13)0.0195 (5)
C380.1105 (2)0.70516 (16)0.64827 (13)0.0181 (5)
C390.0192 (2)0.77089 (18)0.59354 (15)0.0246 (5)
H390.05220.79230.53920.030*
C400.1189 (2)0.80629 (18)0.61587 (16)0.0289 (6)
H400.17940.84980.57700.035*
C410.1671 (2)0.77775 (19)0.69473 (16)0.0298 (6)
H410.26060.80280.71090.036*
C420.0782 (2)0.71239 (19)0.75005 (15)0.0271 (5)
H420.11200.69270.80440.032*
C430.0599 (2)0.67453 (17)0.72839 (14)0.0207 (5)
C440.1433 (3)0.60501 (18)0.79508 (15)0.0278 (6)
O4W0.49901 (19)1.07984 (13)0.32827 (10)0.0323 (4)
H4WA0.48021.12180.28290.048*
H4WB0.49311.10320.36680.048*
O3W0.1356 (2)1.17819 (17)0.00369 (11)0.0541 (6)
H3WA0.07041.23250.00540.081*
H3WB0.14991.13970.05190.081*
O1W0.83173 (16)0.56557 (13)0.38217 (10)0.0274 (4)
H1WA0.79290.51690.38870.041*
H1WB0.77280.61610.39640.041*
O5W0.0946 (2)0.65345 (14)0.99086 (10)0.0366 (5)
H5WA0.09060.61840.95970.055*
H5WB0.11690.61231.03710.055*
O2W0.48153 (18)0.58540 (14)0.34348 (10)0.0329 (4)
H2WA0.54690.52970.34800.049*
H2WB0.49330.62830.29740.049*
O6W0.17069 (16)0.94119 (13)0.61888 (10)0.0261 (4)
H6WA0.21170.99010.60350.039*
H6WB0.22600.88650.60900.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01450 (16)0.01641 (16)0.01615 (17)0.00139 (12)0.00291 (11)0.00300 (12)
O130.0255 (9)0.0189 (8)0.0199 (8)0.0066 (7)0.0021 (7)0.0043 (7)
O10.0246 (9)0.0459 (11)0.0160 (9)0.0034 (8)0.0024 (7)0.0027 (8)
O140.0180 (8)0.0185 (8)0.0253 (9)0.0025 (6)0.0008 (7)0.0051 (7)
O20.0245 (9)0.0380 (10)0.0236 (10)0.0010 (8)0.0017 (8)0.0000 (8)
O120.0252 (9)0.0218 (9)0.0394 (11)0.0065 (7)0.0058 (8)0.0122 (8)
O30.0251 (9)0.0472 (11)0.0170 (9)0.0041 (8)0.0021 (7)0.0009 (8)
O40.0224 (9)0.0372 (10)0.0278 (10)0.0011 (8)0.0028 (8)0.0039 (8)
O50.0147 (8)0.0184 (8)0.0197 (8)0.0039 (6)0.0012 (6)0.0029 (6)
O60.0314 (10)0.0231 (9)0.0383 (11)0.0099 (8)0.0106 (8)0.0137 (8)
O70.0204 (9)0.0369 (10)0.0299 (10)0.0001 (8)0.0027 (8)0.0001 (8)
O80.0274 (10)0.0565 (13)0.0185 (9)0.0002 (9)0.0046 (8)0.0015 (9)
O90.0156 (8)0.0175 (8)0.0220 (8)0.0048 (6)0.0019 (6)0.0029 (6)
O100.0447 (12)0.0505 (12)0.0189 (10)0.0125 (10)0.0028 (8)0.0001 (9)
O110.0278 (10)0.0392 (11)0.0286 (10)0.0014 (8)0.0122 (8)0.0022 (8)
N10.0173 (10)0.0184 (10)0.0206 (10)0.0040 (8)0.0012 (8)0.0057 (8)
N20.0206 (10)0.0265 (11)0.0164 (10)0.0004 (9)0.0056 (8)0.0019 (8)
N30.0204 (11)0.0264 (11)0.0213 (11)0.0007 (9)0.0041 (8)0.0018 (9)
N40.0329 (13)0.0377 (13)0.0256 (12)0.0008 (10)0.0106 (10)0.0045 (10)
N50.0151 (9)0.0181 (10)0.0209 (10)0.0025 (8)0.0017 (8)0.0056 (8)
N60.0180 (10)0.0247 (10)0.0164 (10)0.0017 (8)0.0044 (8)0.0003 (8)
N70.0236 (11)0.0284 (11)0.0210 (11)0.0025 (9)0.0079 (9)0.0015 (9)
N80.0419 (14)0.0304 (12)0.0319 (13)0.0065 (11)0.0149 (11)0.0024 (10)
C10.0207 (12)0.0231 (12)0.0195 (12)0.0008 (10)0.0018 (10)0.0059 (10)
C20.0183 (12)0.0213 (12)0.0210 (12)0.0005 (9)0.0027 (9)0.0056 (10)
C30.0193 (12)0.0172 (11)0.0195 (12)0.0041 (9)0.0028 (9)0.0022 (9)
C40.0220 (12)0.0254 (13)0.0166 (12)0.0034 (10)0.0008 (9)0.0052 (10)
C50.0156 (11)0.0221 (12)0.0205 (12)0.0009 (9)0.0011 (9)0.0057 (10)
C60.0209 (12)0.0224 (12)0.0196 (12)0.0032 (10)0.0029 (10)0.0038 (10)
C70.0227 (13)0.0256 (13)0.0201 (12)0.0014 (10)0.0073 (10)0.0007 (10)
C80.0218 (12)0.0246 (13)0.0208 (12)0.0007 (10)0.0056 (10)0.0011 (10)
C90.0258 (13)0.0214 (12)0.0195 (13)0.0000 (10)0.0033 (10)0.0054 (10)
C100.0275 (13)0.0214 (12)0.0223 (13)0.0000 (10)0.0074 (10)0.0066 (10)
C110.0246 (14)0.0495 (17)0.0231 (14)0.0003 (12)0.0030 (11)0.0040 (12)
C120.0268 (15)0.0543 (18)0.0294 (15)0.0038 (13)0.0063 (12)0.0048 (13)
C130.0376 (15)0.0273 (13)0.0209 (13)0.0082 (11)0.0066 (11)0.0035 (10)
C140.0266 (13)0.0272 (13)0.0251 (13)0.0055 (11)0.0052 (11)0.0048 (11)
C150.0158 (11)0.0216 (12)0.0229 (12)0.0007 (9)0.0019 (9)0.0061 (10)
C160.0195 (12)0.0276 (13)0.0173 (12)0.0015 (10)0.0015 (9)0.0042 (10)
C170.0204 (12)0.0179 (11)0.0196 (12)0.0040 (9)0.0043 (9)0.0033 (9)
C180.0161 (11)0.0217 (12)0.0206 (12)0.0000 (9)0.0013 (9)0.0049 (10)
C190.0198 (12)0.0240 (12)0.0194 (12)0.0017 (10)0.0010 (10)0.0056 (10)
C200.0233 (13)0.0217 (12)0.0186 (12)0.0017 (10)0.0043 (10)0.0022 (10)
C210.0216 (12)0.0261 (13)0.0194 (12)0.0011 (10)0.0069 (10)0.0016 (10)
C220.0239 (13)0.0275 (13)0.0191 (12)0.0015 (10)0.0059 (10)0.0005 (10)
C230.0239 (13)0.0212 (12)0.0227 (13)0.0005 (10)0.0054 (10)0.0068 (10)
C240.0269 (13)0.0227 (12)0.0276 (14)0.0009 (10)0.0114 (11)0.0088 (10)
C250.0321 (15)0.0357 (15)0.0284 (14)0.0087 (12)0.0116 (12)0.0006 (11)
C260.0398 (16)0.0424 (17)0.0288 (15)0.0149 (13)0.0115 (12)0.0032 (12)
C270.0244 (14)0.0378 (16)0.0385 (16)0.0027 (12)0.0125 (12)0.0122 (13)
C280.0260 (14)0.0362 (15)0.0315 (15)0.0005 (12)0.0048 (11)0.0093 (12)
C290.0191 (12)0.0207 (12)0.0171 (12)0.0039 (10)0.0031 (9)0.0030 (9)
C300.0166 (11)0.0175 (11)0.0243 (12)0.0060 (9)0.0018 (9)0.0064 (9)
C310.0252 (13)0.0224 (12)0.0245 (13)0.0064 (10)0.0047 (10)0.0038 (10)
C320.0206 (13)0.0244 (13)0.0377 (15)0.0011 (10)0.0115 (11)0.0053 (11)
C330.0161 (12)0.0289 (14)0.0397 (16)0.0049 (10)0.0005 (11)0.0110 (12)
C340.0227 (13)0.0289 (13)0.0258 (13)0.0085 (11)0.0018 (10)0.0054 (11)
C350.0194 (12)0.0211 (12)0.0244 (13)0.0058 (10)0.0028 (10)0.0070 (10)
C360.0249 (13)0.0224 (12)0.0209 (13)0.0067 (10)0.0022 (10)0.0035 (10)
C370.0202 (12)0.0197 (12)0.0158 (11)0.0022 (10)0.0036 (9)0.0029 (9)
C380.0180 (11)0.0154 (11)0.0218 (12)0.0058 (9)0.0047 (9)0.0034 (9)
C390.0241 (13)0.0241 (12)0.0240 (13)0.0069 (10)0.0060 (10)0.0019 (10)
C400.0207 (13)0.0236 (13)0.0421 (16)0.0007 (10)0.0150 (11)0.0067 (11)
C410.0154 (12)0.0284 (14)0.0467 (17)0.0037 (10)0.0019 (11)0.0143 (12)
C420.0243 (13)0.0324 (14)0.0253 (13)0.0109 (11)0.0051 (10)0.0100 (11)
C430.0191 (12)0.0198 (12)0.0228 (12)0.0063 (9)0.0031 (10)0.0039 (10)
C440.0304 (14)0.0247 (13)0.0302 (15)0.0092 (11)0.0078 (11)0.0056 (11)
O4W0.0384 (11)0.0338 (10)0.0227 (9)0.0029 (8)0.0055 (8)0.0099 (8)
O3W0.0371 (12)0.0618 (15)0.0275 (11)0.0107 (10)0.0018 (9)0.0124 (10)
O1W0.0231 (9)0.0268 (9)0.0323 (10)0.0067 (7)0.0031 (7)0.0109 (8)
O5W0.0392 (11)0.0400 (11)0.0198 (9)0.0005 (9)0.0067 (8)0.0004 (8)
O2W0.0363 (11)0.0298 (10)0.0230 (10)0.0019 (8)0.0049 (8)0.0027 (8)
O6W0.0214 (9)0.0245 (9)0.0307 (10)0.0071 (7)0.0035 (7)0.0074 (8)
Geometric parameters (Å, º) top
Ni1—O132.0643 (15)C12—H120.9500
Ni1—O142.0563 (15)C13—H130.9500
Ni1—O52.1045 (15)C13—C141.389 (3)
Ni1—O92.1274 (15)C14—H140.9500
Ni1—N12.1105 (18)C15—H150.9500
Ni1—N52.1146 (18)C15—C161.383 (3)
O13—H13A0.8839C16—H160.9500
O13—H13B0.8835C16—C171.390 (3)
O1—C61.240 (3)C17—C181.387 (3)
O14—H14A0.8832C17—C201.505 (3)
O14—H14B0.8831C18—H180.9500
O2—C91.233 (3)C18—C191.377 (3)
O12—C371.250 (3)C19—H190.9500
O3—C201.235 (3)C21—H21A0.9900
O4—C231.230 (3)C21—H21B0.9900
O5—C291.269 (3)C21—C221.519 (3)
O6—C291.243 (3)C22—H22A0.9900
O7—C361.213 (3)C22—H22B0.9900
O8—H80.8400C23—C241.510 (3)
O8—C361.311 (3)C24—C251.379 (4)
O9—C371.265 (3)C24—C281.388 (3)
O10—C441.223 (3)C25—H250.9500
O11—H110.8400C25—C261.390 (3)
O11—C441.309 (3)C26—H260.9500
N1—C11.344 (3)C27—H270.9500
N1—C51.342 (3)C27—C281.396 (4)
N2—H20.8800C28—H280.9500
N2—C61.332 (3)C29—C301.515 (3)
N2—C71.465 (3)C30—C311.389 (3)
N3—H30.8800C30—C351.399 (3)
N3—C81.462 (3)C31—H310.9500
N3—C91.326 (3)C31—C321.387 (3)
N4—C121.332 (3)C32—H320.9500
N4—C131.331 (3)C32—C331.384 (4)
N5—C151.340 (3)C33—H330.9500
N5—C191.346 (3)C33—C341.378 (3)
N6—H60.8800C34—H340.9500
N6—C201.332 (3)C34—C351.399 (3)
N6—C211.457 (3)C35—C361.494 (3)
N7—H70.8800C37—C381.516 (3)
N7—C221.462 (3)C38—C391.390 (3)
N7—C231.332 (3)C38—C431.405 (3)
N8—C261.320 (3)C39—H390.9500
N8—C271.332 (4)C39—C401.392 (3)
C1—H10.9500C40—H400.9500
C1—C21.380 (3)C40—C411.377 (4)
C2—H2A0.9500C41—H410.9500
C2—C31.389 (3)C41—C421.380 (3)
C3—C41.397 (3)C42—H420.9500
C3—C61.505 (3)C42—C431.395 (3)
C4—H40.9500C43—C441.496 (3)
C4—C51.378 (3)O4W—H4WA0.8702
C5—H50.9500O4W—H4WB0.8704
C7—H7A0.9900O3W—H3WA0.8695
C7—H7B0.9900O3W—H3WB0.8701
C7—C81.507 (3)O1W—H1WA0.8696
C8—H8A0.9900O1W—H1WB0.8703
C8—H8B0.9900O5W—H5WA0.8698
C9—C101.507 (3)O5W—H5WB0.8699
C10—C111.383 (3)O2W—H2WA0.8698
C10—C141.385 (3)O2W—H2WB0.8693
C11—H11A0.9500O6W—H6WA0.8703
C11—C121.374 (3)O6W—H6WB0.8695
O13—Ni1—O585.98 (6)C17—C16—H16120.2
O13—Ni1—O993.90 (6)C16—C17—C20117.9 (2)
O13—Ni1—N187.30 (7)C18—C17—C16117.6 (2)
O13—Ni1—N592.43 (7)C18—C17—C20124.4 (2)
O14—Ni1—O13179.32 (6)C17—C18—H18120.4
O14—Ni1—O594.34 (6)C19—C18—C17119.2 (2)
O14—Ni1—O985.80 (6)C19—C18—H18120.4
O14—Ni1—N193.30 (7)N5—C19—C18123.5 (2)
O14—Ni1—N586.97 (7)N5—C19—H19118.3
O5—Ni1—O9178.69 (6)C18—C19—H19118.3
O5—Ni1—N188.57 (7)O3—C20—N6122.1 (2)
O5—Ni1—N590.42 (6)O3—C20—C17119.6 (2)
N1—Ni1—O990.12 (7)N6—C20—C17118.2 (2)
N1—Ni1—N5178.97 (7)N6—C21—H21A109.4
N5—Ni1—O990.89 (6)N6—C21—H21B109.4
Ni1—O13—H13A110.3N6—C21—C22111.26 (19)
Ni1—O13—H13B109.9H21A—C21—H21B108.0
H13A—O13—H13B108.6C22—C21—H21A109.4
Ni1—O14—H14A110.1C22—C21—H21B109.4
Ni1—O14—H14B110.2N7—C22—C21108.02 (19)
H14A—O14—H14B108.7N7—C22—H22A110.1
C29—O5—Ni1126.89 (14)N7—C22—H22B110.1
C36—O8—H8109.5C21—C22—H22A110.1
C37—O9—Ni1127.79 (14)C21—C22—H22B110.1
C44—O11—H11109.5H22A—C22—H22B108.4
C1—N1—Ni1120.89 (15)O4—C23—N7123.1 (2)
C5—N1—Ni1122.14 (15)O4—C23—C24119.8 (2)
C5—N1—C1116.97 (19)N7—C23—C24117.0 (2)
C6—N2—H2120.4C25—C24—C23124.5 (2)
C6—N2—C7119.3 (2)C25—C24—C28117.6 (2)
C7—N2—H2120.4C28—C24—C23117.9 (2)
C8—N3—H3119.9C24—C25—H25120.0
C9—N3—H3119.9C24—C25—C26120.0 (3)
C9—N3—C8120.2 (2)C26—C25—H25120.0
C13—N4—C12118.0 (2)N8—C26—C25122.7 (3)
C15—N5—Ni1121.35 (14)N8—C26—H26118.6
C15—N5—C19117.24 (19)C25—C26—H26118.6
C19—N5—Ni1121.35 (15)N8—C27—H27118.4
C20—N6—H6120.7N8—C27—C28123.3 (2)
C20—N6—C21118.59 (19)C28—C27—H27118.4
C21—N6—H6120.7C24—C28—C27118.6 (2)
C22—N7—H7119.4C24—C28—H28120.7
C23—N7—H7119.4C27—C28—H28120.7
C23—N7—C22121.2 (2)O5—C29—C30115.87 (19)
C26—N8—C27117.9 (2)O6—C29—O5125.4 (2)
N1—C1—H1118.1O6—C29—C30118.5 (2)
N1—C1—C2123.9 (2)C31—C30—C29117.1 (2)
C2—C1—H1118.1C31—C30—C35118.8 (2)
C1—C2—H2A120.5C35—C30—C29124.1 (2)
C1—C2—C3119.0 (2)C30—C31—H31119.3
C3—C2—H2A120.5C32—C31—C30121.4 (2)
C2—C3—C4117.4 (2)C32—C31—H31119.3
C2—C3—C6124.3 (2)C31—C32—H32120.1
C4—C3—C6118.3 (2)C33—C32—C31119.8 (2)
C3—C4—H4120.1C33—C32—H32120.1
C5—C4—C3119.8 (2)C32—C33—H33120.3
C5—C4—H4120.1C34—C33—C32119.4 (2)
N1—C5—C4123.0 (2)C34—C33—H33120.3
N1—C5—H5118.5C33—C34—H34119.3
C4—C5—H5118.5C33—C34—C35121.4 (2)
O1—C6—N2122.6 (2)C35—C34—H34119.3
O1—C6—C3119.5 (2)C30—C35—C36121.1 (2)
N2—C6—C3117.8 (2)C34—C35—C30119.1 (2)
N2—C7—H7A109.5C34—C35—C36119.8 (2)
N2—C7—H7B109.5O7—C36—O8123.4 (2)
N2—C7—C8110.80 (19)O7—C36—C35123.5 (2)
H7A—C7—H7B108.1O8—C36—C35113.1 (2)
C8—C7—H7A109.5O12—C37—O9125.5 (2)
C8—C7—H7B109.5O12—C37—C38118.8 (2)
N3—C8—C7108.93 (19)O9—C37—C38115.42 (19)
N3—C8—H8A109.9C39—C38—C37115.1 (2)
N3—C8—H8B109.9C39—C38—C43118.1 (2)
C7—C8—H8A109.9C43—C38—C37126.81 (19)
C7—C8—H8B109.9C38—C39—H39119.0
H8A—C8—H8B108.3C38—C39—C40122.0 (2)
O2—C9—N3122.9 (2)C40—C39—H39119.0
O2—C9—C10118.9 (2)C39—C40—H40120.3
N3—C9—C10118.1 (2)C41—C40—C39119.5 (2)
C11—C10—C9116.9 (2)C41—C40—H40120.3
C11—C10—C14117.7 (2)C40—C41—H41120.3
C14—C10—C9125.4 (2)C40—C41—C42119.4 (2)
C10—C11—H11A120.3C42—C41—H41120.3
C12—C11—C10119.4 (2)C41—C42—H42119.1
C12—C11—H11A120.3C41—C42—C43121.8 (2)
N4—C12—C11123.1 (3)C43—C42—H42119.1
N4—C12—H12118.4C38—C43—C44125.3 (2)
C11—C12—H12118.4C42—C43—C38119.1 (2)
N4—C13—H13118.8C42—C43—C44115.6 (2)
N4—C13—C14122.4 (2)O10—C44—O11123.0 (2)
C14—C13—H13118.8O10—C44—C43121.3 (2)
C10—C14—C13119.4 (2)O11—C44—C43115.7 (2)
C10—C14—H14120.3H4WA—O4W—H4WB109.4
C13—C14—H14120.3H3WA—O3W—H3WB109.5
N5—C15—H15118.6H1WA—O1W—H1WB109.5
N5—C15—C16122.7 (2)H5WA—O5W—H5WB109.5
C16—C15—H15118.6H2WA—O2W—H2WB109.6
C15—C16—H16120.2H6WA—O6W—H6WB109.4
C15—C16—C17119.7 (2)
Ni1—O5—C29—O610.8 (3)C15—N5—C19—C181.4 (3)
Ni1—O5—C29—C30163.86 (14)C15—C16—C17—C181.6 (3)
Ni1—O9—C37—O1214.7 (3)C15—C16—C17—C20179.8 (2)
Ni1—O9—C37—C38158.76 (14)C16—C17—C18—C190.6 (3)
Ni1—N1—C1—C2178.04 (17)C16—C17—C20—O313.8 (3)
Ni1—N1—C5—C4179.25 (17)C16—C17—C20—N6165.5 (2)
Ni1—N5—C15—C16176.37 (17)C17—C18—C19—N52.2 (4)
Ni1—N5—C19—C18178.78 (17)C18—C17—C20—O3164.2 (2)
O2—C9—C10—C1111.9 (3)C18—C17—C20—N616.4 (3)
O2—C9—C10—C14166.1 (2)C19—N5—C15—C161.0 (3)
O12—C37—C38—C39101.6 (2)C20—N6—C21—C22178.2 (2)
O12—C37—C38—C4377.4 (3)C20—C17—C18—C19177.4 (2)
O4—C23—C24—C25168.7 (2)C21—N6—C20—O32.2 (4)
O4—C23—C24—C288.5 (3)C21—N6—C20—C17178.4 (2)
O5—C29—C30—C3177.1 (3)C22—N7—C23—O40.9 (4)
O5—C29—C30—C35104.3 (3)C22—N7—C23—C24177.5 (2)
O6—C29—C30—C3198.0 (3)C23—N7—C22—C21161.1 (2)
O6—C29—C30—C3580.7 (3)C23—C24—C25—C26177.3 (2)
O9—C37—C38—C3972.3 (3)C23—C24—C28—C27177.8 (2)
O9—C37—C38—C43108.7 (3)C24—C25—C26—N80.5 (4)
N1—C1—C2—C32.0 (4)C25—C24—C28—C270.3 (4)
N2—C7—C8—N3179.68 (19)C26—N8—C27—C280.5 (4)
N3—C9—C10—C11168.7 (2)C27—N8—C26—C250.8 (4)
N3—C9—C10—C1413.3 (4)C28—C24—C25—C260.1 (4)
N4—C13—C14—C100.1 (4)C29—C30—C31—C32177.3 (2)
N5—C15—C16—C172.5 (4)C29—C30—C35—C34178.4 (2)
N6—C21—C22—N7179.87 (19)C29—C30—C35—C363.2 (3)
N7—C23—C24—C259.7 (4)C30—C31—C32—C331.7 (4)
N7—C23—C24—C28173.1 (2)C30—C35—C36—O72.0 (4)
N8—C27—C28—C240.0 (4)C30—C35—C36—O8179.0 (2)
C1—N1—C5—C40.4 (3)C31—C30—C35—C340.3 (3)
C1—C2—C3—C41.0 (3)C31—C30—C35—C36178.1 (2)
C1—C2—C3—C6177.0 (2)C31—C32—C33—C340.6 (4)
C2—C3—C4—C50.1 (3)C32—C33—C34—C350.6 (4)
C2—C3—C6—O1165.9 (2)C33—C34—C35—C300.8 (4)
C2—C3—C6—N213.2 (3)C33—C34—C35—C36179.2 (2)
C3—C4—C5—N10.4 (4)C34—C35—C36—O7176.4 (2)
C4—C3—C6—O112.2 (3)C34—C35—C36—O82.6 (3)
C4—C3—C6—N2168.8 (2)C35—C30—C31—C321.5 (3)
C5—N1—C1—C21.7 (3)C37—C38—C39—C40179.0 (2)
C6—N2—C7—C8171.2 (2)C37—C38—C43—C42179.8 (2)
C6—C3—C4—C5178.3 (2)C37—C38—C43—C441.4 (4)
C7—N2—C6—O13.3 (4)C38—C39—C40—C411.6 (4)
C7—N2—C6—C3175.7 (2)C38—C43—C44—O10176.8 (2)
C8—N3—C9—O20.5 (4)C38—C43—C44—O113.5 (3)
C8—N3—C9—C10178.9 (2)C39—C38—C43—C421.2 (3)
C9—N3—C8—C7160.6 (2)C39—C38—C43—C44179.6 (2)
C9—C10—C11—C12178.3 (2)C39—C40—C41—C421.7 (4)
C9—C10—C14—C13177.6 (2)C40—C41—C42—C430.3 (4)
C10—C11—C12—N40.9 (5)C41—C42—C43—C381.2 (4)
C11—C10—C14—C130.4 (4)C41—C42—C43—C44179.7 (2)
C12—N4—C13—C140.6 (4)C42—C43—C44—O104.8 (3)
C13—N4—C12—C111.1 (4)C42—C43—C44—O11174.9 (2)
C14—C10—C11—C120.1 (4)C43—C38—C39—C400.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···N4i0.841.782.609 (3)171
O11—H11···N8ii0.841.822.660 (3)176
O13—H13A···O2W0.881.902.706 (2)150
O13—H13B···O120.881.942.733 (2)149
O14—H14B···O60.881.872.668 (2)149
N2—H2···O1Wiii0.882.022.887 (3)166
N3—H3···O3Wii0.882.022.874 (3)164
N6—H6···O6Wiv0.881.992.844 (3)164
O1W—H1WA···O12v0.871.932.801 (2)177
O1W—H1WB···O50.872.122.967 (2)165
O2W—H2WA···O12v0.872.022.840 (2)158
O2W—H2WB···O2iii0.871.902.757 (2)169
O3W—H3WA···O5Wiv0.871.982.849 (3)173
O3W—H3WB···O30.871.912.777 (2)175
O4W—H4WA···O40.871.962.800 (2)161
O4W—H4WB···O14iv0.871.862.706 (2)165
O5W—H5WA···O100.871.982.821 (3)162
O5W—H5WB···O1vi0.871.922.776 (2)169
O6W—H6WA···O6vii0.871.902.770 (2)178
O6W—H6WB···O90.872.122.977 (2)167
Symmetry codes: (i) x1, y+1, z1; (ii) x+1, y1, z+1; (iii) x+2, y+1, z+1; (iv) x, y+2, z+1; (v) x+1, y+1, z+1; (vi) x+1, y+1, z+2; (vii) x+1, y+2, z+1.
 

Acknowledgements

Funding for this work was provided by the Honors College of Michigan State University.

References

First citationBourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75.  Web of Science CrossRef IUCr Journals Google Scholar
First citationBraverman, M. A., Supkowski, R. M. & LaDuca, R. L. (2007). Inorg. Chim. Acta, 360, 2353–2362.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFilippova, I. G., Gherco, O. A., Simonov, Y. A., Deseatnic-Ciloci, A. A., Clapco, S. F., Tiurina, J. P. & Baca, S. G. (2010). Polyhedron, 29, 1102–1108.  CSD CrossRef CAS Google Scholar
First citationPalmer, D. (2013). Crystal Maker. Crystal Maker Software, Bicester, England.  Google Scholar
First citationQi, Y., Luo, F., Che, Y. & Zheng, J. (2008). Cryst. Growth Des. 8, 606–611.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationZhao, N., Deng, Y., Liu, P., An, C. X., Wang, T. X. & Lian, Z. X. (2015). Polyhedron, 85, 607–614.  CSD CrossRef CAS Google Scholar

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