Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010415/sj2016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010415/sj2016Isup2.hkl |
CCDC reference: 605184
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.030
- wR factor = 0.079
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N4 .. 5.21 su PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.54 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. O6 .. 2.71 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. O2 .. 2.75 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. O2 .. 2.64 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 N3 -NI1 -N1 -C1 -61.60 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 N3 -NI1 -N1 -C22 109.20 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 N4 -NI1 -N2 -C2 -119.90 0.90 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N4 -NI1 -N2 -C3 59.00 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N1 -NI1 -N3 -C9 98.60 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N1 -NI1 -N3 -C12 -75.70 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 20 N2 -NI1 -N4 -C14 87.30 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23 N2 -NI1 -N4 -C13 -85.70 1.00 1.555 1.555 1.555 1.555 PLAT737_ALERT_1_C D...A Calc 3.398(3), Rep 3.398(9) ...... 3.00 su-Rat C12 -O6 1.555 5.577 PLAT737_ALERT_1_C D...A Calc 3.225(3), Rep 3.225(9) ...... 3.00 su-Rat C12 -O4 1.555 2.556 PLAT737_ALERT_1_C D...A Calc 3.068(3), Rep 3.068(9) ...... 3.00 su-Rat C13 -O4 1.555 2.556
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 11 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX II V 1.0-22 (Bruker 2003); cell refinement: SAINT V7.12 (Bruker 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.
C22H18N4NiO6 | F(000) = 2032 |
Mr = 493.11 | Dx = 1.607 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2483 reflections |
a = 25.944 (9) Å | θ = 2.2–25.6° |
b = 8.450 (3) Å | µ = 1.00 mm−1 |
c = 22.105 (12) Å | T = 273 K |
β = 122.747 (3)° | Block, red |
V = 4076 (3) Å3 | 0.20 × 0.12 × 0.10 mm |
Z = 8 |
Bruker APEX II CCD area detector diffractometer | 3602 independent reflections |
Radiation source: fine-focus sealed tube | 2870 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −30→24 |
Tmin = 0.737, Tmax = 0.905 | k = −9→10 |
10646 measured reflections | l = −25→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0456P)2] where P = (Fo2 + 2Fc2)/3 |
3602 reflections | (Δ/σ)max < 0.001 |
300 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Experimental. Spectroscopic analysis: IR (KBr, ν cm-1): 1725, 1671, 1653, 1616, 1592, 1441, 1347, 1210. (IR spectra were recorded on a BIO-RAD FTS 3000 infrared spectrophotometer). Analysis, required for NiC22H18N4O6: C 53.59, H 3.68, N 11.36%; found: C 53.39, H 3.72, N 11.51%. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.082205 (11) | 0.72661 (3) | 0.998512 (14) | 0.02824 (11) | |
O1 | 0.17371 (7) | 0.6609 (3) | 1.20184 (8) | 0.0586 (5) | |
O2 | 0.24595 (7) | 0.5924 (2) | 1.14929 (8) | 0.0511 (5) | |
O3 | 0.12962 (8) | 1.0364 (2) | 0.85400 (8) | 0.0480 (5) | |
O4 | 0.07721 (9) | 0.8438 (3) | 0.77439 (9) | 0.0637 (6) | |
O5 | −0.13223 (7) | 0.7146 (2) | 0.87449 (8) | 0.0439 (4) | |
O6 | −0.12191 (8) | 0.9249 (2) | 0.94179 (10) | 0.0582 (5) | |
N1 | 0.09042 (8) | 0.6589 (2) | 1.08311 (9) | 0.0310 (4) | |
N2 | 0.16055 (7) | 0.6480 (2) | 1.03562 (9) | 0.0310 (4) | |
N3 | 0.07901 (8) | 0.8198 (2) | 0.92026 (9) | 0.0299 (4) | |
N4 | 0.00122 (8) | 0.7907 (2) | 0.95679 (9) | 0.0314 (4) | |
C1 | 0.15112 (10) | 0.6527 (3) | 1.13755 (12) | 0.0374 (6) | |
C2 | 0.19230 (10) | 0.6276 (3) | 1.10799 (12) | 0.0359 (6) | |
C3 | 0.18582 (10) | 0.6094 (3) | 0.99530 (12) | 0.0325 (5) | |
C4 | 0.23100 (10) | 0.4931 (3) | 1.01787 (13) | 0.0413 (6) | |
H4 | 0.2450 | 0.4404 | 1.0610 | 0.050* | |
C5 | 0.25508 (12) | 0.4554 (3) | 0.97758 (15) | 0.0506 (7) | |
H5 | 0.2849 | 0.3770 | 0.9937 | 0.061* | |
C6 | 0.23575 (12) | 0.5318 (3) | 0.91358 (15) | 0.0519 (7) | |
H6 | 0.2530 | 0.5074 | 0.8872 | 0.062* | |
C7 | 0.19110 (11) | 0.6435 (3) | 0.88963 (13) | 0.0428 (6) | |
H7 | 0.1777 | 0.6945 | 0.8463 | 0.051* | |
C8 | 0.16463 (10) | 0.6837 (3) | 0.92862 (12) | 0.0320 (5) | |
C9 | 0.11574 (10) | 0.7996 (3) | 0.89838 (11) | 0.0313 (5) | |
C10 | 0.10501 (11) | 0.8947 (3) | 0.83467 (13) | 0.0409 (6) | |
C11 | 0.12694 (15) | 1.1353 (4) | 0.79849 (16) | 0.0749 (10) | |
H11A | 0.1485 | 1.0844 | 0.7797 | 0.112* | |
H11B | 0.1456 | 1.2358 | 0.8187 | 0.112* | |
H11C | 0.0849 | 1.1511 | 0.7604 | 0.112* | |
C12 | 0.03025 (10) | 0.9395 (3) | 0.88709 (12) | 0.0360 (6) | |
H12A | 0.0187 | 0.9609 | 0.8382 | 0.043* | |
H12B | 0.0441 | 1.0374 | 0.9142 | 0.043* | |
C13 | −0.02358 (10) | 0.8734 (3) | 0.88745 (12) | 0.0390 (6) | |
H13A | −0.0508 | 0.9582 | 0.8826 | 0.047* | |
H13B | −0.0465 | 0.8002 | 0.8478 | 0.047* | |
C14 | −0.03523 (10) | 0.7577 (3) | 0.97815 (12) | 0.0313 (5) | |
C15 | −0.10164 (10) | 0.8103 (3) | 0.93009 (12) | 0.0372 (6) | |
C16 | −0.19546 (11) | 0.7589 (4) | 0.81912 (14) | 0.0594 (8) | |
H16A | −0.2198 | 0.7608 | 0.8398 | 0.089* | |
H16B | −0.2122 | 0.6830 | 0.7807 | 0.089* | |
H16C | −0.1957 | 0.8619 | 0.8006 | 0.089* | |
C17 | −0.01689 (10) | 0.6803 (3) | 1.04514 (11) | 0.0308 (5) | |
C18 | −0.06217 (11) | 0.6509 (3) | 1.06063 (13) | 0.0392 (6) | |
H18 | −0.1025 | 0.6792 | 1.0268 | 0.047* | |
C19 | −0.04887 (12) | 0.5824 (3) | 1.12344 (13) | 0.0452 (6) | |
H19 | −0.0794 | 0.5670 | 1.1329 | 0.054* | |
C20 | 0.01115 (12) | 0.5363 (3) | 1.17303 (13) | 0.0458 (6) | |
H20 | 0.0206 | 0.4870 | 1.2155 | 0.055* | |
C21 | 0.05670 (11) | 0.5624 (3) | 1.16020 (12) | 0.0413 (6) | |
H21 | 0.0965 | 0.5298 | 1.1940 | 0.050* | |
C22 | 0.04439 (10) | 0.6378 (3) | 1.09684 (11) | 0.0307 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02410 (16) | 0.03571 (19) | 0.02549 (16) | 0.00069 (12) | 0.01380 (13) | 0.00005 (12) |
O1 | 0.0364 (10) | 0.1034 (16) | 0.0270 (9) | −0.0081 (10) | 0.0113 (8) | −0.0069 (10) |
O2 | 0.0254 (9) | 0.0813 (14) | 0.0382 (9) | 0.0051 (9) | 0.0117 (7) | 0.0115 (9) |
O3 | 0.0484 (10) | 0.0496 (12) | 0.0427 (10) | −0.0035 (9) | 0.0224 (8) | 0.0126 (9) |
O4 | 0.0713 (14) | 0.0844 (15) | 0.0304 (10) | −0.0074 (11) | 0.0242 (9) | −0.0029 (10) |
O5 | 0.0277 (9) | 0.0527 (11) | 0.0368 (9) | 0.0042 (8) | 0.0080 (7) | −0.0059 (8) |
O6 | 0.0401 (10) | 0.0629 (13) | 0.0637 (12) | 0.0122 (9) | 0.0230 (9) | −0.0142 (10) |
N1 | 0.0281 (10) | 0.0393 (11) | 0.0269 (9) | −0.0006 (8) | 0.0158 (8) | −0.0001 (8) |
N2 | 0.0234 (9) | 0.0400 (12) | 0.0293 (10) | 0.0021 (8) | 0.0141 (8) | 0.0028 (8) |
N3 | 0.0280 (10) | 0.0322 (11) | 0.0268 (9) | −0.0009 (8) | 0.0132 (8) | −0.0013 (8) |
N4 | 0.0295 (10) | 0.0386 (11) | 0.0250 (9) | 0.0015 (8) | 0.0140 (8) | −0.0018 (8) |
C1 | 0.0304 (13) | 0.0487 (16) | 0.0290 (13) | −0.0020 (11) | 0.0134 (11) | 0.0005 (11) |
C2 | 0.0277 (12) | 0.0433 (15) | 0.0320 (13) | −0.0033 (10) | 0.0132 (10) | 0.0022 (11) |
C3 | 0.0263 (11) | 0.0342 (13) | 0.0378 (13) | −0.0036 (10) | 0.0178 (10) | −0.0022 (10) |
C4 | 0.0358 (13) | 0.0428 (15) | 0.0468 (14) | 0.0035 (11) | 0.0233 (12) | 0.0023 (12) |
C5 | 0.0446 (15) | 0.0444 (16) | 0.0695 (19) | 0.0063 (12) | 0.0353 (14) | −0.0038 (14) |
C6 | 0.0503 (16) | 0.0561 (18) | 0.0684 (19) | −0.0009 (14) | 0.0445 (15) | −0.0103 (15) |
C7 | 0.0444 (15) | 0.0480 (16) | 0.0469 (15) | −0.0043 (12) | 0.0318 (12) | −0.0045 (12) |
C8 | 0.0294 (12) | 0.0339 (13) | 0.0363 (12) | −0.0053 (10) | 0.0200 (10) | −0.0041 (10) |
C9 | 0.0312 (12) | 0.0363 (14) | 0.0292 (11) | −0.0078 (10) | 0.0183 (10) | −0.0062 (10) |
C10 | 0.0336 (13) | 0.0566 (18) | 0.0354 (14) | 0.0045 (12) | 0.0204 (11) | 0.0048 (12) |
C11 | 0.080 (2) | 0.075 (2) | 0.074 (2) | 0.0031 (18) | 0.0447 (18) | 0.0373 (18) |
C12 | 0.0388 (13) | 0.0362 (14) | 0.0334 (12) | 0.0056 (10) | 0.0198 (11) | 0.0037 (10) |
C13 | 0.0327 (13) | 0.0521 (16) | 0.0323 (12) | 0.0090 (11) | 0.0176 (10) | 0.0063 (11) |
C14 | 0.0283 (12) | 0.0325 (13) | 0.0328 (12) | −0.0037 (9) | 0.0163 (10) | −0.0099 (10) |
C15 | 0.0310 (13) | 0.0466 (16) | 0.0373 (13) | 0.0007 (11) | 0.0206 (11) | −0.0020 (12) |
C16 | 0.0316 (14) | 0.078 (2) | 0.0463 (16) | 0.0073 (13) | 0.0067 (12) | 0.0020 (14) |
C17 | 0.0303 (12) | 0.0333 (13) | 0.0325 (12) | −0.0062 (10) | 0.0195 (10) | −0.0096 (10) |
C18 | 0.0322 (13) | 0.0421 (15) | 0.0469 (14) | −0.0072 (11) | 0.0238 (11) | −0.0100 (12) |
C19 | 0.0501 (16) | 0.0524 (17) | 0.0513 (16) | −0.0142 (13) | 0.0393 (14) | −0.0111 (13) |
C20 | 0.0539 (17) | 0.0563 (17) | 0.0375 (14) | −0.0092 (13) | 0.0316 (13) | −0.0035 (12) |
C21 | 0.0419 (14) | 0.0517 (16) | 0.0325 (13) | −0.0020 (12) | 0.0216 (11) | 0.0000 (11) |
C22 | 0.0317 (12) | 0.0345 (14) | 0.0296 (12) | −0.0067 (10) | 0.0189 (10) | −0.0095 (10) |
Ni1—N1 | 1.8544 (19) | C6—H6 | 0.9300 |
Ni1—N2 | 1.8553 (18) | C7—C8 | 1.404 (3) |
Ni1—N4 | 1.8605 (19) | C7—H7 | 0.9300 |
Ni1—N3 | 1.861 (2) | C8—C9 | 1.448 (3) |
O1—C1 | 1.211 (3) | C9—C10 | 1.511 (3) |
O2—C2 | 1.218 (3) | C11—H11A | 0.9600 |
O3—C10 | 1.315 (3) | C11—H11B | 0.9600 |
O3—C11 | 1.455 (3) | C11—H11C | 0.9600 |
O4—C10 | 1.200 (3) | C12—C13 | 1.508 (3) |
O5—C15 | 1.319 (3) | C12—H12A | 0.9700 |
O5—C16 | 1.469 (3) | C12—H12B | 0.9700 |
O6—C15 | 1.195 (3) | C13—H13A | 0.9700 |
N1—C1 | 1.371 (3) | C13—H13B | 0.9700 |
N1—C22 | 1.394 (3) | C14—C17 | 1.444 (3) |
N2—C2 | 1.357 (3) | C14—C15 | 1.521 (3) |
N2—C3 | 1.401 (3) | C16—H16A | 0.9600 |
N3—C9 | 1.292 (3) | C16—H16B | 0.9600 |
N3—C12 | 1.469 (3) | C16—H16C | 0.9600 |
N4—C14 | 1.295 (3) | C17—C18 | 1.412 (3) |
N4—C13 | 1.478 (3) | C17—C22 | 1.413 (3) |
C1—C2 | 1.539 (3) | C18—C19 | 1.365 (3) |
C3—C4 | 1.398 (3) | C18—H18 | 0.9300 |
C3—C8 | 1.412 (3) | C19—C20 | 1.390 (3) |
C4—C5 | 1.374 (3) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.374 (3) |
C5—C6 | 1.379 (4) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.409 (3) |
C6—C7 | 1.360 (4) | C21—H21 | 0.9300 |
N1—Ni1—N2 | 86.72 (8) | O3—C10—C9 | 111.7 (2) |
N1—Ni1—N4 | 94.17 (8) | O3—C11—H11A | 109.5 |
N2—Ni1—N4 | 175.35 (8) | O3—C11—H11B | 109.5 |
N1—Ni1—N3 | 172.24 (8) | H11A—C11—H11B | 109.5 |
N2—Ni1—N3 | 92.86 (8) | O3—C11—H11C | 109.5 |
N4—Ni1—N3 | 86.88 (8) | H11A—C11—H11C | 109.5 |
C10—O3—C11 | 117.1 (2) | H11B—C11—H11C | 109.5 |
C15—O5—C16 | 117.25 (19) | N3—C12—C13 | 107.01 (19) |
C1—N1—C22 | 121.10 (18) | N3—C12—H12A | 110.3 |
C1—N1—Ni1 | 110.35 (15) | C13—C12—H12A | 110.3 |
C22—N1—Ni1 | 127.92 (14) | N3—C12—H12B | 110.3 |
C2—N2—C3 | 121.74 (18) | C13—C12—H12B | 110.3 |
C2—N2—Ni1 | 112.81 (14) | H12A—C12—H12B | 108.6 |
C3—N2—Ni1 | 125.44 (14) | N4—C13—C12 | 107.21 (17) |
C9—N3—C12 | 121.00 (19) | N4—C13—H13A | 110.3 |
C9—N3—Ni1 | 128.35 (16) | C12—C13—H13A | 110.3 |
C12—N3—Ni1 | 110.40 (14) | N4—C13—H13B | 110.3 |
C14—N4—C13 | 119.04 (19) | C12—C13—H13B | 110.3 |
C14—N4—Ni1 | 127.46 (16) | H13A—C13—H13B | 108.5 |
C13—N4—Ni1 | 113.14 (14) | N4—C14—C17 | 124.8 (2) |
O1—C1—N1 | 128.7 (2) | N4—C14—C15 | 117.2 (2) |
O1—C1—C2 | 120.0 (2) | C17—C14—C15 | 117.96 (19) |
N1—C1—C2 | 111.35 (19) | O6—C15—O5 | 125.8 (2) |
O2—C2—N2 | 129.3 (2) | O6—C15—C14 | 123.4 (2) |
O2—C2—C1 | 119.3 (2) | O5—C15—C14 | 110.78 (19) |
N2—C2—C1 | 111.41 (18) | O5—C16—H16A | 109.5 |
C4—C3—N2 | 121.8 (2) | O5—C16—H16B | 109.5 |
C4—C3—C8 | 117.6 (2) | H16A—C16—H16B | 109.5 |
N2—C3—C8 | 120.6 (2) | O5—C16—H16C | 109.5 |
C5—C4—C3 | 121.3 (2) | H16A—C16—H16C | 109.5 |
C5—C4—H4 | 119.4 | H16B—C16—H16C | 109.5 |
C3—C4—H4 | 119.4 | C18—C17—C22 | 118.6 (2) |
C4—C5—C6 | 121.0 (2) | C18—C17—C14 | 118.2 (2) |
C4—C5—H5 | 119.5 | C22—C17—C14 | 123.2 (2) |
C6—C5—H5 | 119.5 | C19—C18—C17 | 122.4 (2) |
C7—C6—C5 | 119.0 (2) | C19—C18—H18 | 118.8 |
C7—C6—H6 | 120.5 | C17—C18—H18 | 118.8 |
C5—C6—H6 | 120.5 | C18—C19—C20 | 118.7 (2) |
C6—C7—C8 | 121.7 (2) | C18—C19—H19 | 120.7 |
C6—C7—H7 | 119.1 | C20—C19—H19 | 120.7 |
C8—C7—H7 | 119.1 | C21—C20—C19 | 120.9 (2) |
C7—C8—C3 | 119.3 (2) | C21—C20—H20 | 119.5 |
C7—C8—C9 | 118.5 (2) | C19—C20—H20 | 119.5 |
C3—C8—C9 | 122.12 (19) | C20—C21—C22 | 121.3 (2) |
N3—C9—C8 | 123.8 (2) | C20—C21—H21 | 119.3 |
N3—C9—C10 | 118.5 (2) | C22—C21—H21 | 119.3 |
C8—C9—C10 | 117.61 (19) | N1—C22—C21 | 120.9 (2) |
O4—C10—O3 | 125.5 (2) | N1—C22—C17 | 120.9 (2) |
O4—C10—C9 | 122.8 (3) | C21—C22—C17 | 118.0 (2) |
N2—Ni1—N1—C1 | 25.48 (17) | N2—C3—C8—C9 | −1.2 (3) |
N4—Ni1—N1—C1 | −159.10 (16) | C12—N3—C9—C8 | −179.9 (2) |
N3—Ni1—N1—C1 | −61.6 (6) | Ni1—N3—C9—C8 | 6.4 (3) |
N2—Ni1—N1—C22 | −163.7 (2) | C12—N3—C9—C10 | −3.8 (3) |
N4—Ni1—N1—C22 | 11.7 (2) | Ni1—N3—C9—C10 | −177.48 (16) |
N3—Ni1—N1—C22 | 109.2 (5) | C7—C8—C9—N3 | 163.7 (2) |
N1—Ni1—N2—C2 | −18.82 (17) | C3—C8—C9—N3 | −15.5 (3) |
N4—Ni1—N2—C2 | −119.9 (9) | C7—C8—C9—C10 | −12.4 (3) |
N3—Ni1—N2—C2 | 153.43 (16) | C3—C8—C9—C10 | 168.3 (2) |
N1—Ni1—N2—C3 | 160.10 (19) | C11—O3—C10—O4 | −5.0 (4) |
N4—Ni1—N2—C3 | 59.0 (10) | C11—O3—C10—C9 | 175.1 (2) |
N3—Ni1—N2—C3 | −27.65 (19) | N3—C9—C10—O4 | −96.4 (3) |
N1—Ni1—N3—C9 | 98.6 (6) | C8—C9—C10—O4 | 79.9 (3) |
N2—Ni1—N3—C9 | 11.9 (2) | N3—C9—C10—O3 | 83.5 (3) |
N4—Ni1—N3—C9 | −163.4 (2) | C8—C9—C10—O3 | −100.1 (2) |
N1—Ni1—N3—C12 | −75.7 (6) | C9—N3—C12—C13 | 145.4 (2) |
N2—Ni1—N3—C12 | −162.31 (15) | Ni1—N3—C12—C13 | −39.9 (2) |
N4—Ni1—N3—C12 | 22.34 (15) | C14—N4—C13—C12 | 163.0 (2) |
N1—Ni1—N4—C14 | −13.5 (2) | Ni1—N4—C13—C12 | −23.3 (2) |
N2—Ni1—N4—C14 | 87.3 (10) | N3—C12—C13—N4 | 39.6 (2) |
N3—Ni1—N4—C14 | 174.20 (19) | C13—N4—C14—C17 | −178.8 (2) |
N1—Ni1—N4—C13 | 173.48 (16) | Ni1—N4—C14—C17 | 8.6 (3) |
N2—Ni1—N4—C13 | −85.7 (10) | C13—N4—C14—C15 | −1.1 (3) |
N3—Ni1—N4—C13 | 1.18 (16) | Ni1—N4—C14—C15 | −173.76 (15) |
C22—N1—C1—O1 | −15.9 (4) | C16—O5—C15—O6 | 4.9 (4) |
Ni1—N1—C1—O1 | 155.7 (2) | C16—O5—C15—C14 | −173.9 (2) |
C22—N1—C1—C2 | 162.4 (2) | N4—C14—C15—O6 | −101.4 (3) |
Ni1—N1—C1—C2 | −26.0 (2) | C17—C14—C15—O6 | 76.4 (3) |
C3—N2—C2—O2 | 8.5 (4) | N4—C14—C15—O5 | 77.5 (3) |
Ni1—N2—C2—O2 | −172.6 (2) | C17—C14—C15—O5 | −104.7 (2) |
C3—N2—C2—C1 | −170.7 (2) | N4—C14—C17—C18 | −179.4 (2) |
Ni1—N2—C2—C1 | 8.3 (2) | C15—C14—C17—C18 | 3.0 (3) |
O1—C1—C2—O2 | 11.0 (4) | N4—C14—C17—C22 | 2.9 (3) |
N1—C1—C2—O2 | −167.4 (2) | C15—C14—C17—C22 | −174.7 (2) |
O1—C1—C2—N2 | −169.7 (2) | C22—C17—C18—C19 | −0.3 (4) |
N1—C1—C2—N2 | 11.8 (3) | C14—C17—C18—C19 | −178.1 (2) |
C2—N2—C3—C4 | 27.0 (3) | C17—C18—C19—C20 | −1.8 (4) |
Ni1—N2—C3—C4 | −151.82 (18) | C18—C19—C20—C21 | 1.7 (4) |
C2—N2—C3—C8 | −155.2 (2) | C19—C20—C21—C22 | 0.5 (4) |
Ni1—N2—C3—C8 | 25.9 (3) | C1—N1—C22—C21 | −20.0 (3) |
N2—C3—C4—C5 | 179.4 (2) | Ni1—N1—C22—C21 | 170.11 (17) |
C8—C3—C4—C5 | 1.6 (3) | C1—N1—C22—C17 | 165.0 (2) |
C3—C4—C5—C6 | 0.5 (4) | Ni1—N1—C22—C17 | −5.0 (3) |
C4—C5—C6—C7 | −1.6 (4) | C20—C21—C22—N1 | −177.7 (2) |
C5—C6—C7—C8 | 0.6 (4) | C20—C21—C22—C17 | −2.5 (3) |
C6—C7—C8—C3 | 1.5 (4) | C18—C17—C22—N1 | 177.6 (2) |
C6—C7—C8—C9 | −177.8 (2) | C14—C17—C22—N1 | −4.7 (3) |
C4—C3—C8—C7 | −2.6 (3) | C18—C17—C22—C21 | 2.4 (3) |
N2—C3—C8—C7 | 179.6 (2) | C14—C17—C22—C21 | −179.9 (2) |
C4—C3—C8—C9 | 176.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12B···O6i | 0.97 | 2.71 | 3.398 (9) | 128 |
C12—H12A···O4ii | 0.97 | 2.58 | 3.225 (9) | 124 |
C13—H13B···O4ii | 0.97 | 2.39 | 3.068 (9) | 126 |
C11—H11A···O2iii | 0.96 | 2.75 | 3.434 (9) | 129 |
C7—H7···O2iii | 0.93 | 2.64 | 3.148 (4) | 115 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, y, −z+3/2; (iii) −x+1/2, −y+3/2, −z+2. |