metal-organic compounds
Diaquabis[N,N′-(ethane-1,2-diyl)bis(isonicotinamide)-κN]bis(hydrogen phthalato-κO)nickel(II) hexahydrate
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 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.
Keywords: crystal structure; nickel complex; phtalate ligand; hydrogen bonding.
CCDC reference: 1494370
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). 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). [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). [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).
The II cation, two Hpht− ligands, two aqua ligands, two ebin ligands, thus forming the coordination complex [Ni(Hpht)2(ebin)2(H2O)2] (Fig. 1). Six water molecules of crystallization also reside in the 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) and angles confirm an octahedral coordination environment for the NiII atom.
of the title compound contains one Ni
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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). 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). 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) 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).
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 .
details are summarized in Table 3
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Structural data
CCDC reference: 1494370
https://doi.org/10.1107/S2414314616011676/wm4020sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616011676/wm4020Isup2.hkl
3D Molecule View. DOI: https://doi.org/10.1107/S2414314616011676/wm4020sup3.tif
Data collection: APEX2 (Bruker, 2014); cell
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).[Ni(C8H5O4)2(C14H14N4O2)2(H2O)2]·6H2O | Z = 2 |
Mr = 1073.64 | F(000) = 1124 |
Triclinic, P1 | Dx = 1.507 Mg m−3 |
a = 10.2857 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.3250 (17) Å | Cell parameters from 9906 reflections |
c = 17.794 (2) Å | θ = 2.3–25.3° |
α = 71.528 (1)° | µ = 0.50 mm−1 |
β = 79.919 (1)° | T = 173 K |
γ = 72.784 (1)° | Block, green |
V = 2365.7 (5) Å3 | 0.27 × 0.21 × 0.10 mm |
Bruker APEXII CCD diffractometer | 8669 independent reflections |
Radiation source: sealed tube | 6860 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 836.6 pixels mm-1 | θmax = 25.4°, θmin = 1.6° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −17→17 |
Tmin = 0.711, Tmax = 0.745 | l = −21→21 |
36698 measured reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H-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 reflections | Δρmax = 0.64 e Å−3 |
680 parameters | Δρmin = −0.64 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.49745 (3) | 0.74721 (2) | 0.50914 (2) | 0.01646 (10) | |
O1 | 0.82860 (17) | 0.45611 (14) | 0.85737 (10) | 0.0331 (4) | |
O2 | 1.51830 (17) | 0.27370 (13) | 0.80397 (10) | 0.0325 (4) | |
O3 | 0.19602 (17) | 1.05743 (14) | 0.15603 (10) | 0.0352 (5) | |
O4 | −0.50372 (17) | 1.22484 (13) | 0.17927 (10) | 0.0318 (4) | |
O5 | 0.67444 (15) | 0.75127 (11) | 0.42961 (9) | 0.0183 (3) | |
O6 | 0.70332 (17) | 0.90064 (12) | 0.42718 (11) | 0.0308 (4) | |
O7 | 0.69349 (17) | 0.91897 (13) | 0.25517 (10) | 0.0330 (4) | |
O8 | 0.86509 (18) | 0.92196 (16) | 0.15992 (10) | 0.0391 (5) | |
H8 | 0.8015 | 0.9572 | 0.1310 | 0.059* | |
O9 | 0.32138 (15) | 0.74082 (11) | 0.59165 (9) | 0.0189 (3) | |
O10 | 0.0904 (2) | 0.57849 (15) | 0.86281 (10) | 0.0404 (5) | |
O11 | 0.27474 (18) | 0.57567 (14) | 0.77595 (10) | 0.0351 (4) | |
H11 | 0.3138 | 0.5379 | 0.8167 | 0.053* | |
O12 | 0.29879 (17) | 0.58649 (12) | 0.60231 (10) | 0.0290 (4) | |
O13 | 0.50251 (16) | 0.61563 (11) | 0.48298 (9) | 0.0215 (4) | |
H13A | 0.4871 | 0.6295 | 0.4328 | 0.032* | |
H13B | 0.4390 | 0.5874 | 0.5137 | 0.032* | |
O14 | 0.49020 (16) | 0.87908 (11) | 0.53467 (9) | 0.0215 (4) | |
H14A | 0.4099 | 0.9230 | 0.5253 | 0.032* | |
H14B | 0.5544 | 0.9071 | 0.5047 | 0.032* | |
N1 | 0.62369 (18) | 0.65432 (14) | 0.60069 (11) | 0.0189 (4) | |
N2 | 1.01031 (19) | 0.41926 (14) | 0.77027 (11) | 0.0229 (4) | |
H2 | 1.0458 | 0.4305 | 0.7205 | 0.028* | |
N3 | 1.3188 (2) | 0.24783 (15) | 0.86972 (12) | 0.0257 (5) | |
H3 | 1.2765 | 0.2163 | 0.9135 | 0.031* | |
N4 | 1.6880 (2) | 0.03666 (17) | 1.05794 (13) | 0.0340 (5) | |
N5 | 0.37401 (18) | 0.83994 (14) | 0.41590 (11) | 0.0184 (4) | |
N6 | 0.00097 (19) | 1.07507 (14) | 0.23624 (11) | 0.0215 (4) | |
H6 | −0.0409 | 1.0584 | 0.2842 | 0.026* | |
N7 | −0.2954 (2) | 1.24525 (15) | 0.12505 (12) | 0.0266 (5) | |
H7 | −0.2473 | 1.2755 | 0.0835 | 0.032* | |
N8 | −0.6137 (2) | 1.45381 (16) | −0.09158 (13) | 0.0354 (5) | |
C1 | 0.7449 (2) | 0.59222 (17) | 0.58465 (14) | 0.0222 (5) | |
H1 | 0.7707 | 0.5898 | 0.5312 | 0.027* | |
C2 | 0.8340 (2) | 0.53179 (17) | 0.64121 (13) | 0.0214 (5) | |
H2A | 0.9198 | 0.4908 | 0.6264 | 0.026* | |
C3 | 0.7964 (2) | 0.53183 (16) | 0.72011 (13) | 0.0194 (5) | |
C4 | 0.6697 (2) | 0.59523 (17) | 0.73731 (14) | 0.0225 (5) | |
H4 | 0.6400 | 0.5975 | 0.7905 | 0.027* | |
C5 | 0.5880 (2) | 0.65450 (17) | 0.67687 (13) | 0.0204 (5) | |
H5 | 0.5025 | 0.6974 | 0.6897 | 0.025* | |
C6 | 0.8811 (2) | 0.46600 (17) | 0.78795 (14) | 0.0219 (5) | |
C7 | 1.0928 (2) | 0.34900 (18) | 0.83455 (14) | 0.0246 (5) | |
H7A | 1.0571 | 0.2880 | 0.8585 | 0.030* | |
H7B | 1.0858 | 0.3825 | 0.8765 | 0.030* | |
C8 | 1.2404 (2) | 0.31724 (18) | 0.80369 (14) | 0.0247 (5) | |
H8A | 1.2482 | 0.2829 | 0.7622 | 0.030* | |
H8B | 1.2767 | 0.3780 | 0.7797 | 0.030* | |
C9 | 1.4533 (2) | 0.23228 (18) | 0.86387 (14) | 0.0235 (5) | |
C10 | 1.5292 (2) | 0.16153 (17) | 0.93421 (14) | 0.0244 (5) | |
C11 | 1.6701 (3) | 0.1322 (2) | 0.92201 (16) | 0.0360 (7) | |
H11A | 1.7150 | 0.1548 | 0.8708 | 0.043* | |
C12 | 1.7447 (3) | 0.0699 (2) | 0.98459 (16) | 0.0413 (7) | |
H12 | 1.8414 | 0.0496 | 0.9751 | 0.050* | |
C13 | 1.5523 (3) | 0.06410 (19) | 1.07036 (15) | 0.0289 (6) | |
H13 | 1.5106 | 0.0403 | 1.1223 | 0.035* | |
C14 | 1.4696 (3) | 0.12619 (18) | 1.01016 (14) | 0.0269 (6) | |
H14 | 1.3730 | 0.1442 | 1.0210 | 0.032* | |
C15 | 0.4203 (2) | 0.84744 (17) | 0.33952 (14) | 0.0211 (5) | |
H15 | 0.5086 | 0.8070 | 0.3278 | 0.025* | |
C16 | 0.3449 (2) | 0.91165 (18) | 0.27709 (14) | 0.0230 (5) | |
H16 | 0.3829 | 0.9168 | 0.2237 | 0.028* | |
C17 | 0.2134 (2) | 0.96857 (17) | 0.29281 (13) | 0.0197 (5) | |
C18 | 0.1646 (2) | 0.95989 (17) | 0.37186 (13) | 0.0209 (5) | |
H18 | 0.0749 | 0.9969 | 0.3853 | 0.025* | |
C19 | 0.2478 (2) | 0.89696 (17) | 0.43065 (14) | 0.0222 (5) | |
H19 | 0.2142 | 0.8936 | 0.4844 | 0.027* | |
C20 | 0.1352 (2) | 1.03773 (17) | 0.22313 (14) | 0.0227 (5) | |
C21 | −0.0749 (2) | 1.14415 (18) | 0.16946 (14) | 0.0240 (5) | |
H21A | −0.0615 | 1.1101 | 0.1272 | 0.029* | |
H21B | −0.0392 | 1.2053 | 0.1473 | 0.029* | |
C22 | −0.2266 (2) | 1.17618 (19) | 0.19489 (14) | 0.0258 (5) | |
H22A | −0.2637 | 1.1156 | 0.2165 | 0.031* | |
H22B | −0.2413 | 1.2110 | 0.2368 | 0.031* | |
C23 | −0.4296 (2) | 1.26325 (17) | 0.12320 (14) | 0.0235 (5) | |
C24 | −0.4899 (2) | 1.33226 (18) | 0.04703 (15) | 0.0254 (5) | |
C25 | −0.4141 (3) | 1.3655 (2) | −0.02330 (15) | 0.0330 (6) | |
H25 | −0.3171 | 1.3472 | −0.0254 | 0.040* | |
C26 | −0.4795 (3) | 1.4256 (2) | −0.09107 (16) | 0.0382 (7) | |
H26 | −0.4253 | 1.4472 | −0.1390 | 0.046* | |
C27 | −0.6881 (3) | 1.4218 (2) | −0.02409 (16) | 0.0344 (6) | |
H27 | −0.7848 | 1.4414 | −0.0241 | 0.041* | |
C28 | −0.6311 (3) | 1.3610 (2) | 0.04669 (16) | 0.0327 (6) | |
H28 | −0.6878 | 1.3397 | 0.0936 | 0.039* | |
C29 | 0.7415 (2) | 0.81806 (17) | 0.41064 (13) | 0.0196 (5) | |
C30 | 0.8842 (2) | 0.78887 (16) | 0.37059 (14) | 0.0190 (5) | |
C31 | 0.9853 (2) | 0.72325 (18) | 0.41893 (15) | 0.0243 (5) | |
H31 | 0.9616 | 0.6968 | 0.4741 | 0.029* | |
C32 | 1.1202 (2) | 0.69546 (18) | 0.38840 (16) | 0.0283 (6) | |
H32 | 1.1883 | 0.6519 | 0.4227 | 0.034* | |
C33 | 1.1552 (2) | 0.73139 (19) | 0.30775 (16) | 0.0285 (6) | |
H33 | 1.2472 | 0.7122 | 0.2863 | 0.034* | |
C34 | 1.0555 (2) | 0.79525 (18) | 0.25885 (15) | 0.0265 (5) | |
H34 | 1.0796 | 0.8193 | 0.2034 | 0.032* | |
C35 | 0.9196 (2) | 0.82543 (17) | 0.28905 (14) | 0.0213 (5) | |
C36 | 0.8142 (2) | 0.89364 (18) | 0.23390 (14) | 0.0232 (5) | |
C37 | 0.2565 (2) | 0.67276 (17) | 0.61349 (13) | 0.0195 (5) | |
C38 | 0.1105 (2) | 0.70516 (16) | 0.64827 (13) | 0.0181 (5) | |
C39 | 0.0192 (2) | 0.77089 (18) | 0.59354 (15) | 0.0246 (5) | |
H39 | 0.0522 | 0.7923 | 0.5392 | 0.030* | |
C40 | −0.1189 (2) | 0.80629 (18) | 0.61587 (16) | 0.0289 (6) | |
H40 | −0.1794 | 0.8498 | 0.5770 | 0.035* | |
C41 | −0.1671 (2) | 0.77775 (19) | 0.69473 (16) | 0.0298 (6) | |
H41 | −0.2606 | 0.8028 | 0.7109 | 0.036* | |
C42 | −0.0782 (2) | 0.71239 (19) | 0.75005 (15) | 0.0271 (5) | |
H42 | −0.1120 | 0.6927 | 0.8044 | 0.032* | |
C43 | 0.0599 (2) | 0.67453 (17) | 0.72839 (14) | 0.0207 (5) | |
C44 | 0.1433 (3) | 0.60501 (18) | 0.79508 (15) | 0.0278 (6) | |
O4W | −0.49901 (19) | 1.07984 (13) | 0.32827 (10) | 0.0323 (4) | |
H4WA | −0.4802 | 1.1218 | 0.2829 | 0.048* | |
H4WB | −0.4931 | 1.1032 | 0.3668 | 0.048* | |
O3W | 0.1356 (2) | 1.17819 (17) | 0.00369 (11) | 0.0541 (6) | |
H3WA | 0.0704 | 1.2325 | 0.0054 | 0.081* | |
H3WB | 0.1499 | 1.1397 | 0.0519 | 0.081* | |
O1W | 0.83173 (16) | 0.56557 (13) | 0.38217 (10) | 0.0274 (4) | |
H1WA | 0.7929 | 0.5169 | 0.3887 | 0.041* | |
H1WB | 0.7728 | 0.6161 | 0.3964 | 0.041* | |
O5W | 0.0946 (2) | 0.65345 (14) | 0.99086 (10) | 0.0366 (5) | |
H5WA | 0.0906 | 0.6184 | 0.9597 | 0.055* | |
H5WB | 0.1169 | 0.6123 | 1.0371 | 0.055* | |
O2W | 0.48153 (18) | 0.58540 (14) | 0.34348 (10) | 0.0329 (4) | |
H2WA | 0.5469 | 0.5297 | 0.3480 | 0.049* | |
H2WB | 0.4933 | 0.6283 | 0.2974 | 0.049* | |
O6W | 0.17069 (16) | 0.94119 (13) | 0.61888 (10) | 0.0261 (4) | |
H6WA | 0.2117 | 0.9901 | 0.6035 | 0.039* | |
H6WB | 0.2260 | 0.8865 | 0.6090 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.01450 (16) | 0.01641 (16) | 0.01615 (17) | −0.00139 (12) | −0.00291 (11) | −0.00300 (12) |
O13 | 0.0255 (9) | 0.0189 (8) | 0.0199 (8) | −0.0066 (7) | −0.0021 (7) | −0.0043 (7) |
O1 | 0.0246 (9) | 0.0459 (11) | 0.0160 (9) | 0.0034 (8) | −0.0024 (7) | −0.0027 (8) |
O14 | 0.0180 (8) | 0.0185 (8) | 0.0253 (9) | −0.0025 (6) | −0.0008 (7) | −0.0051 (7) |
O2 | 0.0245 (9) | 0.0380 (10) | 0.0236 (10) | −0.0010 (8) | −0.0017 (8) | 0.0000 (8) |
O12 | 0.0252 (9) | 0.0218 (9) | 0.0394 (11) | −0.0065 (7) | 0.0058 (8) | −0.0122 (8) |
O3 | 0.0251 (9) | 0.0472 (11) | 0.0170 (9) | 0.0041 (8) | −0.0021 (7) | 0.0009 (8) |
O4 | 0.0224 (9) | 0.0372 (10) | 0.0278 (10) | −0.0011 (8) | −0.0028 (8) | −0.0039 (8) |
O5 | 0.0147 (8) | 0.0184 (8) | 0.0197 (8) | −0.0039 (6) | −0.0012 (6) | −0.0029 (6) |
O6 | 0.0314 (10) | 0.0231 (9) | 0.0383 (11) | −0.0099 (8) | 0.0106 (8) | −0.0137 (8) |
O7 | 0.0204 (9) | 0.0369 (10) | 0.0299 (10) | 0.0001 (8) | −0.0027 (8) | −0.0001 (8) |
O8 | 0.0274 (10) | 0.0565 (13) | 0.0185 (9) | −0.0002 (9) | −0.0046 (8) | 0.0015 (9) |
O9 | 0.0156 (8) | 0.0175 (8) | 0.0220 (8) | −0.0048 (6) | −0.0019 (6) | −0.0029 (6) |
O10 | 0.0447 (12) | 0.0505 (12) | 0.0189 (10) | −0.0125 (10) | −0.0028 (8) | 0.0001 (9) |
O11 | 0.0278 (10) | 0.0392 (11) | 0.0286 (10) | −0.0014 (8) | −0.0122 (8) | 0.0022 (8) |
N1 | 0.0173 (10) | 0.0184 (10) | 0.0206 (10) | −0.0040 (8) | −0.0012 (8) | −0.0057 (8) |
N2 | 0.0206 (10) | 0.0265 (11) | 0.0164 (10) | −0.0004 (9) | −0.0056 (8) | −0.0019 (8) |
N3 | 0.0204 (11) | 0.0264 (11) | 0.0213 (11) | −0.0007 (9) | −0.0041 (8) | 0.0018 (9) |
N4 | 0.0329 (13) | 0.0377 (13) | 0.0256 (12) | −0.0008 (10) | −0.0106 (10) | −0.0045 (10) |
N5 | 0.0151 (9) | 0.0181 (10) | 0.0209 (10) | −0.0025 (8) | −0.0017 (8) | −0.0056 (8) |
N6 | 0.0180 (10) | 0.0247 (10) | 0.0164 (10) | −0.0017 (8) | −0.0044 (8) | −0.0003 (8) |
N7 | 0.0236 (11) | 0.0284 (11) | 0.0210 (11) | −0.0025 (9) | −0.0079 (9) | 0.0015 (9) |
N8 | 0.0419 (14) | 0.0304 (12) | 0.0319 (13) | −0.0065 (11) | −0.0149 (11) | −0.0024 (10) |
C1 | 0.0207 (12) | 0.0231 (12) | 0.0195 (12) | −0.0008 (10) | −0.0018 (10) | −0.0059 (10) |
C2 | 0.0183 (12) | 0.0213 (12) | 0.0210 (12) | 0.0005 (9) | −0.0027 (9) | −0.0056 (10) |
C3 | 0.0193 (12) | 0.0172 (11) | 0.0195 (12) | −0.0041 (9) | −0.0028 (9) | −0.0022 (9) |
C4 | 0.0220 (12) | 0.0254 (13) | 0.0166 (12) | −0.0034 (10) | 0.0008 (9) | −0.0052 (10) |
C5 | 0.0156 (11) | 0.0221 (12) | 0.0205 (12) | −0.0009 (9) | −0.0011 (9) | −0.0057 (10) |
C6 | 0.0209 (12) | 0.0224 (12) | 0.0196 (12) | −0.0032 (10) | −0.0029 (10) | −0.0038 (10) |
C7 | 0.0227 (13) | 0.0256 (13) | 0.0201 (12) | −0.0014 (10) | −0.0073 (10) | −0.0007 (10) |
C8 | 0.0218 (12) | 0.0246 (13) | 0.0208 (12) | 0.0007 (10) | −0.0056 (10) | −0.0011 (10) |
C9 | 0.0258 (13) | 0.0214 (12) | 0.0195 (13) | 0.0000 (10) | −0.0033 (10) | −0.0054 (10) |
C10 | 0.0275 (13) | 0.0214 (12) | 0.0223 (13) | 0.0000 (10) | −0.0074 (10) | −0.0066 (10) |
C11 | 0.0246 (14) | 0.0495 (17) | 0.0231 (14) | 0.0003 (12) | −0.0030 (11) | −0.0040 (12) |
C12 | 0.0268 (15) | 0.0543 (18) | 0.0294 (15) | 0.0038 (13) | −0.0063 (12) | −0.0048 (13) |
C13 | 0.0376 (15) | 0.0273 (13) | 0.0209 (13) | −0.0082 (11) | −0.0066 (11) | −0.0035 (10) |
C14 | 0.0266 (13) | 0.0272 (13) | 0.0251 (13) | −0.0055 (11) | −0.0052 (11) | −0.0048 (11) |
C15 | 0.0158 (11) | 0.0216 (12) | 0.0229 (12) | −0.0007 (9) | −0.0019 (9) | −0.0061 (10) |
C16 | 0.0195 (12) | 0.0276 (13) | 0.0173 (12) | −0.0015 (10) | −0.0015 (9) | −0.0042 (10) |
C17 | 0.0204 (12) | 0.0179 (11) | 0.0196 (12) | −0.0040 (9) | −0.0043 (9) | −0.0033 (9) |
C18 | 0.0161 (11) | 0.0217 (12) | 0.0206 (12) | 0.0000 (9) | −0.0013 (9) | −0.0049 (10) |
C19 | 0.0198 (12) | 0.0240 (12) | 0.0194 (12) | −0.0017 (10) | −0.0010 (10) | −0.0056 (10) |
C20 | 0.0233 (13) | 0.0217 (12) | 0.0186 (12) | −0.0017 (10) | −0.0043 (10) | −0.0022 (10) |
C21 | 0.0216 (12) | 0.0261 (13) | 0.0194 (12) | −0.0011 (10) | −0.0069 (10) | −0.0016 (10) |
C22 | 0.0239 (13) | 0.0275 (13) | 0.0191 (12) | −0.0015 (10) | −0.0059 (10) | 0.0005 (10) |
C23 | 0.0239 (13) | 0.0212 (12) | 0.0227 (13) | 0.0005 (10) | −0.0054 (10) | −0.0068 (10) |
C24 | 0.0269 (13) | 0.0227 (12) | 0.0276 (14) | −0.0009 (10) | −0.0114 (11) | −0.0088 (10) |
C25 | 0.0321 (15) | 0.0357 (15) | 0.0284 (14) | −0.0087 (12) | −0.0116 (12) | −0.0006 (11) |
C26 | 0.0398 (16) | 0.0424 (17) | 0.0288 (15) | −0.0149 (13) | −0.0115 (12) | 0.0032 (12) |
C27 | 0.0244 (14) | 0.0378 (16) | 0.0385 (16) | 0.0027 (12) | −0.0125 (12) | −0.0122 (13) |
C28 | 0.0260 (14) | 0.0362 (15) | 0.0315 (15) | −0.0005 (12) | −0.0048 (11) | −0.0093 (12) |
C29 | 0.0191 (12) | 0.0207 (12) | 0.0171 (12) | −0.0039 (10) | −0.0031 (9) | −0.0030 (9) |
C30 | 0.0166 (11) | 0.0175 (11) | 0.0243 (12) | −0.0060 (9) | −0.0018 (9) | −0.0064 (9) |
C31 | 0.0252 (13) | 0.0224 (12) | 0.0245 (13) | −0.0064 (10) | −0.0047 (10) | −0.0038 (10) |
C32 | 0.0206 (13) | 0.0244 (13) | 0.0377 (15) | −0.0011 (10) | −0.0115 (11) | −0.0053 (11) |
C33 | 0.0161 (12) | 0.0289 (14) | 0.0397 (16) | −0.0049 (10) | 0.0005 (11) | −0.0110 (12) |
C34 | 0.0227 (13) | 0.0289 (13) | 0.0258 (13) | −0.0085 (11) | 0.0018 (10) | −0.0054 (11) |
C35 | 0.0194 (12) | 0.0211 (12) | 0.0244 (13) | −0.0058 (10) | −0.0028 (10) | −0.0070 (10) |
C36 | 0.0249 (13) | 0.0224 (12) | 0.0209 (13) | −0.0067 (10) | −0.0022 (10) | −0.0035 (10) |
C37 | 0.0202 (12) | 0.0197 (12) | 0.0158 (11) | −0.0022 (10) | −0.0036 (9) | −0.0029 (9) |
C38 | 0.0180 (11) | 0.0154 (11) | 0.0218 (12) | −0.0058 (9) | −0.0047 (9) | −0.0034 (9) |
C39 | 0.0241 (13) | 0.0241 (12) | 0.0240 (13) | −0.0069 (10) | −0.0060 (10) | −0.0019 (10) |
C40 | 0.0207 (13) | 0.0236 (13) | 0.0421 (16) | −0.0007 (10) | −0.0150 (11) | −0.0067 (11) |
C41 | 0.0154 (12) | 0.0284 (14) | 0.0467 (17) | −0.0037 (10) | −0.0019 (11) | −0.0143 (12) |
C42 | 0.0243 (13) | 0.0324 (14) | 0.0253 (13) | −0.0109 (11) | 0.0051 (10) | −0.0100 (11) |
C43 | 0.0191 (12) | 0.0198 (12) | 0.0228 (12) | −0.0063 (9) | −0.0031 (10) | −0.0039 (10) |
C44 | 0.0304 (14) | 0.0247 (13) | 0.0302 (15) | −0.0092 (11) | −0.0078 (11) | −0.0056 (11) |
O4W | 0.0384 (11) | 0.0338 (10) | 0.0227 (9) | −0.0029 (8) | −0.0055 (8) | −0.0099 (8) |
O3W | 0.0371 (12) | 0.0618 (15) | 0.0275 (11) | 0.0107 (10) | 0.0018 (9) | 0.0124 (10) |
O1W | 0.0231 (9) | 0.0268 (9) | 0.0323 (10) | −0.0067 (7) | 0.0031 (7) | −0.0109 (8) |
O5W | 0.0392 (11) | 0.0400 (11) | 0.0198 (9) | −0.0005 (9) | −0.0067 (8) | −0.0004 (8) |
O2W | 0.0363 (11) | 0.0298 (10) | 0.0230 (10) | 0.0019 (8) | −0.0049 (8) | −0.0027 (8) |
O6W | 0.0214 (9) | 0.0245 (9) | 0.0307 (10) | −0.0071 (7) | 0.0035 (7) | −0.0074 (8) |
Ni1—O13 | 2.0643 (15) | C12—H12 | 0.9500 |
Ni1—O14 | 2.0563 (15) | C13—H13 | 0.9500 |
Ni1—O5 | 2.1045 (15) | C13—C14 | 1.389 (3) |
Ni1—O9 | 2.1274 (15) | C14—H14 | 0.9500 |
Ni1—N1 | 2.1105 (18) | C15—H15 | 0.9500 |
Ni1—N5 | 2.1146 (18) | C15—C16 | 1.383 (3) |
O13—H13A | 0.8839 | C16—H16 | 0.9500 |
O13—H13B | 0.8835 | C16—C17 | 1.390 (3) |
O1—C6 | 1.240 (3) | C17—C18 | 1.387 (3) |
O14—H14A | 0.8832 | C17—C20 | 1.505 (3) |
O14—H14B | 0.8831 | C18—H18 | 0.9500 |
O2—C9 | 1.233 (3) | C18—C19 | 1.377 (3) |
O12—C37 | 1.250 (3) | C19—H19 | 0.9500 |
O3—C20 | 1.235 (3) | C21—H21A | 0.9900 |
O4—C23 | 1.230 (3) | C21—H21B | 0.9900 |
O5—C29 | 1.269 (3) | C21—C22 | 1.519 (3) |
O6—C29 | 1.243 (3) | C22—H22A | 0.9900 |
O7—C36 | 1.213 (3) | C22—H22B | 0.9900 |
O8—H8 | 0.8400 | C23—C24 | 1.510 (3) |
O8—C36 | 1.311 (3) | C24—C25 | 1.379 (4) |
O9—C37 | 1.265 (3) | C24—C28 | 1.388 (3) |
O10—C44 | 1.223 (3) | C25—H25 | 0.9500 |
O11—H11 | 0.8400 | C25—C26 | 1.390 (3) |
O11—C44 | 1.309 (3) | C26—H26 | 0.9500 |
N1—C1 | 1.344 (3) | C27—H27 | 0.9500 |
N1—C5 | 1.342 (3) | C27—C28 | 1.396 (4) |
N2—H2 | 0.8800 | C28—H28 | 0.9500 |
N2—C6 | 1.332 (3) | C29—C30 | 1.515 (3) |
N2—C7 | 1.465 (3) | C30—C31 | 1.389 (3) |
N3—H3 | 0.8800 | C30—C35 | 1.399 (3) |
N3—C8 | 1.462 (3) | C31—H31 | 0.9500 |
N3—C9 | 1.326 (3) | C31—C32 | 1.387 (3) |
N4—C12 | 1.332 (3) | C32—H32 | 0.9500 |
N4—C13 | 1.331 (3) | C32—C33 | 1.384 (4) |
N5—C15 | 1.340 (3) | C33—H33 | 0.9500 |
N5—C19 | 1.346 (3) | C33—C34 | 1.378 (3) |
N6—H6 | 0.8800 | C34—H34 | 0.9500 |
N6—C20 | 1.332 (3) | C34—C35 | 1.399 (3) |
N6—C21 | 1.457 (3) | C35—C36 | 1.494 (3) |
N7—H7 | 0.8800 | C37—C38 | 1.516 (3) |
N7—C22 | 1.462 (3) | C38—C39 | 1.390 (3) |
N7—C23 | 1.332 (3) | C38—C43 | 1.405 (3) |
N8—C26 | 1.320 (3) | C39—H39 | 0.9500 |
N8—C27 | 1.332 (4) | C39—C40 | 1.392 (3) |
C1—H1 | 0.9500 | C40—H40 | 0.9500 |
C1—C2 | 1.380 (3) | C40—C41 | 1.377 (4) |
C2—H2A | 0.9500 | C41—H41 | 0.9500 |
C2—C3 | 1.389 (3) | C41—C42 | 1.380 (3) |
C3—C4 | 1.397 (3) | C42—H42 | 0.9500 |
C3—C6 | 1.505 (3) | C42—C43 | 1.395 (3) |
C4—H4 | 0.9500 | C43—C44 | 1.496 (3) |
C4—C5 | 1.378 (3) | O4W—H4WA | 0.8702 |
C5—H5 | 0.9500 | O4W—H4WB | 0.8704 |
C7—H7A | 0.9900 | O3W—H3WA | 0.8695 |
C7—H7B | 0.9900 | O3W—H3WB | 0.8701 |
C7—C8 | 1.507 (3) | O1W—H1WA | 0.8696 |
C8—H8A | 0.9900 | O1W—H1WB | 0.8703 |
C8—H8B | 0.9900 | O5W—H5WA | 0.8698 |
C9—C10 | 1.507 (3) | O5W—H5WB | 0.8699 |
C10—C11 | 1.383 (3) | O2W—H2WA | 0.8698 |
C10—C14 | 1.385 (3) | O2W—H2WB | 0.8693 |
C11—H11A | 0.9500 | O6W—H6WA | 0.8703 |
C11—C12 | 1.374 (3) | O6W—H6WB | 0.8695 |
O13—Ni1—O5 | 85.98 (6) | C17—C16—H16 | 120.2 |
O13—Ni1—O9 | 93.90 (6) | C16—C17—C20 | 117.9 (2) |
O13—Ni1—N1 | 87.30 (7) | C18—C17—C16 | 117.6 (2) |
O13—Ni1—N5 | 92.43 (7) | C18—C17—C20 | 124.4 (2) |
O14—Ni1—O13 | 179.32 (6) | C17—C18—H18 | 120.4 |
O14—Ni1—O5 | 94.34 (6) | C19—C18—C17 | 119.2 (2) |
O14—Ni1—O9 | 85.80 (6) | C19—C18—H18 | 120.4 |
O14—Ni1—N1 | 93.30 (7) | N5—C19—C18 | 123.5 (2) |
O14—Ni1—N5 | 86.97 (7) | N5—C19—H19 | 118.3 |
O5—Ni1—O9 | 178.69 (6) | C18—C19—H19 | 118.3 |
O5—Ni1—N1 | 88.57 (7) | O3—C20—N6 | 122.1 (2) |
O5—Ni1—N5 | 90.42 (6) | O3—C20—C17 | 119.6 (2) |
N1—Ni1—O9 | 90.12 (7) | N6—C20—C17 | 118.2 (2) |
N1—Ni1—N5 | 178.97 (7) | N6—C21—H21A | 109.4 |
N5—Ni1—O9 | 90.89 (6) | N6—C21—H21B | 109.4 |
Ni1—O13—H13A | 110.3 | N6—C21—C22 | 111.26 (19) |
Ni1—O13—H13B | 109.9 | H21A—C21—H21B | 108.0 |
H13A—O13—H13B | 108.6 | C22—C21—H21A | 109.4 |
Ni1—O14—H14A | 110.1 | C22—C21—H21B | 109.4 |
Ni1—O14—H14B | 110.2 | N7—C22—C21 | 108.02 (19) |
H14A—O14—H14B | 108.7 | N7—C22—H22A | 110.1 |
C29—O5—Ni1 | 126.89 (14) | N7—C22—H22B | 110.1 |
C36—O8—H8 | 109.5 | C21—C22—H22A | 110.1 |
C37—O9—Ni1 | 127.79 (14) | C21—C22—H22B | 110.1 |
C44—O11—H11 | 109.5 | H22A—C22—H22B | 108.4 |
C1—N1—Ni1 | 120.89 (15) | O4—C23—N7 | 123.1 (2) |
C5—N1—Ni1 | 122.14 (15) | O4—C23—C24 | 119.8 (2) |
C5—N1—C1 | 116.97 (19) | N7—C23—C24 | 117.0 (2) |
C6—N2—H2 | 120.4 | C25—C24—C23 | 124.5 (2) |
C6—N2—C7 | 119.3 (2) | C25—C24—C28 | 117.6 (2) |
C7—N2—H2 | 120.4 | C28—C24—C23 | 117.9 (2) |
C8—N3—H3 | 119.9 | C24—C25—H25 | 120.0 |
C9—N3—H3 | 119.9 | C24—C25—C26 | 120.0 (3) |
C9—N3—C8 | 120.2 (2) | C26—C25—H25 | 120.0 |
C13—N4—C12 | 118.0 (2) | N8—C26—C25 | 122.7 (3) |
C15—N5—Ni1 | 121.35 (14) | N8—C26—H26 | 118.6 |
C15—N5—C19 | 117.24 (19) | C25—C26—H26 | 118.6 |
C19—N5—Ni1 | 121.35 (15) | N8—C27—H27 | 118.4 |
C20—N6—H6 | 120.7 | N8—C27—C28 | 123.3 (2) |
C20—N6—C21 | 118.59 (19) | C28—C27—H27 | 118.4 |
C21—N6—H6 | 120.7 | C24—C28—C27 | 118.6 (2) |
C22—N7—H7 | 119.4 | C24—C28—H28 | 120.7 |
C23—N7—H7 | 119.4 | C27—C28—H28 | 120.7 |
C23—N7—C22 | 121.2 (2) | O5—C29—C30 | 115.87 (19) |
C26—N8—C27 | 117.9 (2) | O6—C29—O5 | 125.4 (2) |
N1—C1—H1 | 118.1 | O6—C29—C30 | 118.5 (2) |
N1—C1—C2 | 123.9 (2) | C31—C30—C29 | 117.1 (2) |
C2—C1—H1 | 118.1 | C31—C30—C35 | 118.8 (2) |
C1—C2—H2A | 120.5 | C35—C30—C29 | 124.1 (2) |
C1—C2—C3 | 119.0 (2) | C30—C31—H31 | 119.3 |
C3—C2—H2A | 120.5 | C32—C31—C30 | 121.4 (2) |
C2—C3—C4 | 117.4 (2) | C32—C31—H31 | 119.3 |
C2—C3—C6 | 124.3 (2) | C31—C32—H32 | 120.1 |
C4—C3—C6 | 118.3 (2) | C33—C32—C31 | 119.8 (2) |
C3—C4—H4 | 120.1 | C33—C32—H32 | 120.1 |
C5—C4—C3 | 119.8 (2) | C32—C33—H33 | 120.3 |
C5—C4—H4 | 120.1 | C34—C33—C32 | 119.4 (2) |
N1—C5—C4 | 123.0 (2) | C34—C33—H33 | 120.3 |
N1—C5—H5 | 118.5 | C33—C34—H34 | 119.3 |
C4—C5—H5 | 118.5 | C33—C34—C35 | 121.4 (2) |
O1—C6—N2 | 122.6 (2) | C35—C34—H34 | 119.3 |
O1—C6—C3 | 119.5 (2) | C30—C35—C36 | 121.1 (2) |
N2—C6—C3 | 117.8 (2) | C34—C35—C30 | 119.1 (2) |
N2—C7—H7A | 109.5 | C34—C35—C36 | 119.8 (2) |
N2—C7—H7B | 109.5 | O7—C36—O8 | 123.4 (2) |
N2—C7—C8 | 110.80 (19) | O7—C36—C35 | 123.5 (2) |
H7A—C7—H7B | 108.1 | O8—C36—C35 | 113.1 (2) |
C8—C7—H7A | 109.5 | O12—C37—O9 | 125.5 (2) |
C8—C7—H7B | 109.5 | O12—C37—C38 | 118.8 (2) |
N3—C8—C7 | 108.93 (19) | O9—C37—C38 | 115.42 (19) |
N3—C8—H8A | 109.9 | C39—C38—C37 | 115.1 (2) |
N3—C8—H8B | 109.9 | C39—C38—C43 | 118.1 (2) |
C7—C8—H8A | 109.9 | C43—C38—C37 | 126.81 (19) |
C7—C8—H8B | 109.9 | C38—C39—H39 | 119.0 |
H8A—C8—H8B | 108.3 | C38—C39—C40 | 122.0 (2) |
O2—C9—N3 | 122.9 (2) | C40—C39—H39 | 119.0 |
O2—C9—C10 | 118.9 (2) | C39—C40—H40 | 120.3 |
N3—C9—C10 | 118.1 (2) | C41—C40—C39 | 119.5 (2) |
C11—C10—C9 | 116.9 (2) | C41—C40—H40 | 120.3 |
C11—C10—C14 | 117.7 (2) | C40—C41—H41 | 120.3 |
C14—C10—C9 | 125.4 (2) | C40—C41—C42 | 119.4 (2) |
C10—C11—H11A | 120.3 | C42—C41—H41 | 120.3 |
C12—C11—C10 | 119.4 (2) | C41—C42—H42 | 119.1 |
C12—C11—H11A | 120.3 | C41—C42—C43 | 121.8 (2) |
N4—C12—C11 | 123.1 (3) | C43—C42—H42 | 119.1 |
N4—C12—H12 | 118.4 | C38—C43—C44 | 125.3 (2) |
C11—C12—H12 | 118.4 | C42—C43—C38 | 119.1 (2) |
N4—C13—H13 | 118.8 | C42—C43—C44 | 115.6 (2) |
N4—C13—C14 | 122.4 (2) | O10—C44—O11 | 123.0 (2) |
C14—C13—H13 | 118.8 | O10—C44—C43 | 121.3 (2) |
C10—C14—C13 | 119.4 (2) | O11—C44—C43 | 115.7 (2) |
C10—C14—H14 | 120.3 | H4WA—O4W—H4WB | 109.4 |
C13—C14—H14 | 120.3 | H3WA—O3W—H3WB | 109.5 |
N5—C15—H15 | 118.6 | H1WA—O1W—H1WB | 109.5 |
N5—C15—C16 | 122.7 (2) | H5WA—O5W—H5WB | 109.5 |
C16—C15—H15 | 118.6 | H2WA—O2W—H2WB | 109.6 |
C15—C16—H16 | 120.2 | H6WA—O6W—H6WB | 109.4 |
C15—C16—C17 | 119.7 (2) | ||
Ni1—O5—C29—O6 | −10.8 (3) | C15—N5—C19—C18 | 1.4 (3) |
Ni1—O5—C29—C30 | 163.86 (14) | C15—C16—C17—C18 | 1.6 (3) |
Ni1—O9—C37—O12 | 14.7 (3) | C15—C16—C17—C20 | 179.8 (2) |
Ni1—O9—C37—C38 | −158.76 (14) | C16—C17—C18—C19 | 0.6 (3) |
Ni1—N1—C1—C2 | 178.04 (17) | C16—C17—C20—O3 | −13.8 (3) |
Ni1—N1—C5—C4 | −179.25 (17) | C16—C17—C20—N6 | 165.5 (2) |
Ni1—N5—C15—C16 | −176.37 (17) | C17—C18—C19—N5 | −2.2 (4) |
Ni1—N5—C19—C18 | 178.78 (17) | C18—C17—C20—O3 | 164.2 (2) |
O2—C9—C10—C11 | −11.9 (3) | C18—C17—C20—N6 | −16.4 (3) |
O2—C9—C10—C14 | 166.1 (2) | C19—N5—C15—C16 | 1.0 (3) |
O12—C37—C38—C39 | −101.6 (2) | C20—N6—C21—C22 | 178.2 (2) |
O12—C37—C38—C43 | 77.4 (3) | C20—C17—C18—C19 | −177.4 (2) |
O4—C23—C24—C25 | −168.7 (2) | C21—N6—C20—O3 | −2.2 (4) |
O4—C23—C24—C28 | 8.5 (3) | C21—N6—C20—C17 | 178.4 (2) |
O5—C29—C30—C31 | −77.1 (3) | C22—N7—C23—O4 | 0.9 (4) |
O5—C29—C30—C35 | 104.3 (3) | C22—N7—C23—C24 | −177.5 (2) |
O6—C29—C30—C31 | 98.0 (3) | C23—N7—C22—C21 | 161.1 (2) |
O6—C29—C30—C35 | −80.7 (3) | C23—C24—C25—C26 | 177.3 (2) |
O9—C37—C38—C39 | 72.3 (3) | C23—C24—C28—C27 | −177.8 (2) |
O9—C37—C38—C43 | −108.7 (3) | C24—C25—C26—N8 | 0.5 (4) |
N1—C1—C2—C3 | 2.0 (4) | C25—C24—C28—C27 | −0.3 (4) |
N2—C7—C8—N3 | 179.68 (19) | C26—N8—C27—C28 | 0.5 (4) |
N3—C9—C10—C11 | 168.7 (2) | C27—N8—C26—C25 | −0.8 (4) |
N3—C9—C10—C14 | −13.3 (4) | C28—C24—C25—C26 | 0.1 (4) |
N4—C13—C14—C10 | −0.1 (4) | C29—C30—C31—C32 | −177.3 (2) |
N5—C15—C16—C17 | −2.5 (4) | C29—C30—C35—C34 | 178.4 (2) |
N6—C21—C22—N7 | 179.87 (19) | C29—C30—C35—C36 | −3.2 (3) |
N7—C23—C24—C25 | 9.7 (4) | C30—C31—C32—C33 | −1.7 (4) |
N7—C23—C24—C28 | −173.1 (2) | C30—C35—C36—O7 | −2.0 (4) |
N8—C27—C28—C24 | 0.0 (4) | C30—C35—C36—O8 | 179.0 (2) |
C1—N1—C5—C4 | 0.4 (3) | C31—C30—C35—C34 | −0.3 (3) |
C1—C2—C3—C4 | −1.0 (3) | C31—C30—C35—C36 | 178.1 (2) |
C1—C2—C3—C6 | 177.0 (2) | C31—C32—C33—C34 | 0.6 (4) |
C2—C3—C4—C5 | −0.1 (3) | C32—C33—C34—C35 | 0.6 (4) |
C2—C3—C6—O1 | −165.9 (2) | C33—C34—C35—C30 | −0.8 (4) |
C2—C3—C6—N2 | 13.2 (3) | C33—C34—C35—C36 | −179.2 (2) |
C3—C4—C5—N1 | 0.4 (4) | C34—C35—C36—O7 | 176.4 (2) |
C4—C3—C6—O1 | 12.2 (3) | C34—C35—C36—O8 | −2.6 (3) |
C4—C3—C6—N2 | −168.8 (2) | C35—C30—C31—C32 | 1.5 (3) |
C5—N1—C1—C2 | −1.7 (3) | C37—C38—C39—C40 | 179.0 (2) |
C6—N2—C7—C8 | −171.2 (2) | C37—C38—C43—C42 | 179.8 (2) |
C6—C3—C4—C5 | −178.3 (2) | C37—C38—C43—C44 | 1.4 (4) |
C7—N2—C6—O1 | 3.3 (4) | C38—C39—C40—C41 | 1.6 (4) |
C7—N2—C6—C3 | −175.7 (2) | C38—C43—C44—O10 | −176.8 (2) |
C8—N3—C9—O2 | −0.5 (4) | C38—C43—C44—O11 | 3.5 (3) |
C8—N3—C9—C10 | 178.9 (2) | C39—C38—C43—C42 | −1.2 (3) |
C9—N3—C8—C7 | −160.6 (2) | C39—C38—C43—C44 | −179.6 (2) |
C9—C10—C11—C12 | 178.3 (2) | C39—C40—C41—C42 | −1.7 (4) |
C9—C10—C14—C13 | −177.6 (2) | C40—C41—C42—C43 | 0.3 (4) |
C10—C11—C12—N4 | −0.9 (5) | C41—C42—C43—C38 | 1.2 (4) |
C11—C10—C14—C13 | 0.4 (4) | C41—C42—C43—C44 | 179.7 (2) |
C12—N4—C13—C14 | −0.6 (4) | C42—C43—C44—O10 | 4.8 (3) |
C13—N4—C12—C11 | 1.1 (4) | C42—C43—C44—O11 | −174.9 (2) |
C14—C10—C11—C12 | 0.1 (4) | C43—C38—C39—C40 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | 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. |
Acknowledgements
Funding for this work was provided by the Honors College of Michigan State University.
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