Journal Information

Journal ID (publisher-id): chemical

Title: Journal of the Korean Chemical Society

Translated Title (ko): 대한화학회지

ISSN (print): 1017-2548

ISSN (electronic): 2234-8530

Publisher: Korean Chemical Society대한화학회

Article Information

Copyright statement: Copyright © 2018, Korean Chemical Society

Copyright: 2018

Date received: 31 August 2018

Date accepted: 16 September 2018

Publication date (print): 20 December 2018

Volume: 62

Issue: 6

Pages: 1-10

Publisher ID: jkcs-62-s427

DOI: 10.5012/jkcs.2018.62.6.1

Synthesis and Characterization of Nickel(II) Tetraaza Macrocyclic Complex with 1,1-Cyclohexanediacetate Ligand

In-Taek Lim[†]

Chong-Hyeak Kim[‡]

Ki-Young Choi[§][*]

[†] Department of Center for Teaching and Learning, Chunnam Techno University, Gokseong 57500, Korea

[‡] Center for Chemical Analysis, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-Ro, Yuseong-Gu, Daejeon 34114, Korea

[§] Department of Chemistry Education, Kongju National University, Kongju 32588, Korea.

Author notes:

Correspondence to: [*] E-mail: kychoi@kongju.ac.kr

Expand AllCollapse All

Computing details

Data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS-97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL-97 (Sheldrick, 2008); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Crystal data

C30H54N4NiO4

  • Z = 2

Mr = 593.48

  • F(000) = 644

Triclinic, P¯1

  • Dx = 1.248 Mg m-3

  • Dm = 0 Mg m-3

  • Dm measured by ?

a = 11.3918 (7) Å

  • Mo Kα radiation, λ = 0.71073 Å

b = 12.6196 (8) Å

  • Cell parameters from 3846 reflections
c = 12.8700 (8) Å

  • θ = 2.5–24.6°
α = 69.572 (4)°

  • μ = 0.65 mm-1
β = 83.516 (4)°

  • T = 296 K

γ = 65.753 (4)°

  • Block, purple
V = 1579.88 (17) Å3

  • 0.14 × 0.08 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer 7837 independent reflections
Radiation source: fine-focus sealed tube 4651 reflections with I > 2σ(I)
graphite Rint = 0.0000
φ and ω scans θmax = 28.5°, θmin = 1.7°
Absorption correction: multi-scan ? h = -15→15
Tmin = 0.914, Tmax = 0.962 k = -15→16
7837 measured reflections l = 0→17

Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.276 w = 1 / σ 2 F o 2 + 0.1639 P 2 + 0.266 P where  P = F o 2 + 2 F e 2 / 3
S = 1.07 (Δ/σ)max < 0.001
7837 reflections Δ〉max = 1.95 e Å-3
356 parameters Δ〉min = -0.51 e Å-3
0 restraints Extinction correction: SHELXL, Fc* = kFc[1+0.001×Fc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.004 (2)

Special details

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. 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Ni1 0.5000 0.0000 0.5000 0.0318 (2)
Ni2 0.0000 0.5000 0.0000 0.0310 (2)
O1 0.4918 (3) 0.1775 (3) 0.3785 (3) 0.0388 (7)
O2 0.5807 (4) 0.1291 (3) 0.2300 (3) 0.0702 (13)
O3 0.1073 (3) 0.4854 (3) 0.1351 (2) 0.0381 (7)
O4 0.2237 (4) 0.2838 (3) 0.2178 (3) 0.0526 (9)
N1 0.5763 (3) -0.0880 (3) 0.3846 (3) 0.0337 (8)
HN1 0.5825 -0.0279 0.3199 0.040*
N2 0.3077 (3) 0.0700 (3) 0.4456 (3) 0.0336 (8)
HN2 0.2975 0.1417 0.3864 0.040*
N3 0.1067 (4) 0.3187 (3) 0.0142 (3) 0.0338 (8)
HN3 0.1644 0.2857 0.0741 0.041*
N4 -0.1322 (3) 0.4321 (3) 0.0941 (3) 0.0341 (8)
HN4 -0.1892 0.4453 0.0400 0.041*
C1 0.2266 (4) 0.1148 (4) 0.5323 (4) 0.0365 (10)
H1 0.2231 0.0415 0.5943 0.044*
C2 0.0883 (4) 0.2027 (5) 0.4907 (4) 0.0480 (12)
H2A 0.0897 0.2736 0.4262 0.058*
H2B 0.0479 0.1593 0.4656 0.058*
C3 0.0083 (5) 0.2496 (6) 0.5797 (5) 0.0613 (16)
H3A -0.0029 0.1802 0.6400 0.074*
H3B -0.0780 0.3110 0.5478 0.074*
C4 0.9271 (5) -0.3092 (5) 0.3722 (5) 0.0608 (15)
H4A 0.9778 -0.3333 0.3104 0.073*
H4B 0.9255 -0.3847 0.4303 0.073*
C5 0.7903 (5) -0.2203 (5) 0.3303 (4) 0.0509 (13)
H5A 0.7495 -0.2618 0.3029 0.061*
H5B 0.7925 -0.1484 0.2675 0.061*
C6 0.7099 (4) -0.1760 (4) 0.4217 (4) 0.0348 (10)
H6 0.7066 -0.2495 0.4833 0.042*
C7 0.4957 (5) -0.1391 (4) 0.3554 (4) 0.0415 (11)
H7A 0.4877 -0.2055 0.4215 0.050*
H7B 0.5375 -0.1759 0.2974 0.050*
C8 0.3637 (5) -0.0420 (4) 0.3137 (4) 0.0437 (11)
H8A 0.3255 -0.0727 0.2711 0.052*
H8B 0.3745 0.0319 0.2608 0.052*
C9 0.2658 (4) -0.0007 (4) 0.3986 (4) 0.0398 (11)
H9 0.1817 0.0568 0.3576 0.048*
C10 0.2443 (6) -0.1067 (5) 0.4864 (5) 0.0553 (14)
H10A 0.3248 -0.1638 0.5296 0.083*
H10B 0.2166 -0.1502 0.4509 0.083*
H10C 0.1776 -0.0750 0.5359 0.083*
C11 -0.0677 (4) 0.2966 (4) 0.1379 (4) 0.0357 (10)
H11 -0.0104 0.2732 0.2026 0.043*
C12 -0.1603 (5) 0.2323 (5) 0.1761 (4) 0.0488 (12)
H12A -0.2218 0.2593 0.1143 0.059*
H12B -0.2103 0.2570 0.2380 0.059*
C13 -0.0894 (6) 0.0918 (5) 0.2145 (5) 0.0562 (14)
H13A -0.0340 0.0638 0.2808 0.067*
H13B -0.1530 0.0536 0.2354 0.067*
C14 -0.0074 (6) 0.0504 (5) 0.1236 (5) 0.0576 (15)
H14A -0.0636 0.0716 0.0598 0.069*
H14B 0.0406 -0.0403 0.1514 0.069*
C15 0.0870 (5) 0.1118 (4) 0.0859 (5) 0.0481 (12)
H15A 0.1370 0.0859 0.0245 0.058*
H15B 0.1482 0.0842 0.1480 0.058*
C16 0.0175 (4) 0.2545 (4) 0.0460 (4) 0.0369 (10)
H16 -0.0394 0.2813 -0.0200 0.044*
C17 0.1844 (5) 0.2998 (4) -0.0822 (4) 0.0402 (11)
H17A 0.1264 0.3320 -0.1478 0.048*
H17B 0.2341 0.2104 -0.0674 0.048*
C18 -0.2763 (4) 0.6363 (4) 0.1074 (4) 0.0422 (11)
H18A -0.3168 0.6522 0.0364 0.051*
H18B -0.3457 0.6754 0.1525 0.051*
C19 -0.2195 (5) 0.4943 (4) 0.1694 (4) 0.0425 (11)
H19 -0.2929 0.4676 0.1841 0.051*
C20 -0.1550 (6) 0.4574 (5) 0.2787 (4) 0.0534 (14)
H20A -0.1410 0.3717 0.3214 0.080*
H20B -0.2098 0.5112 0.3199 0.080*
H20C -0.0720 0.4651 0.2665 0.080*
C21 0.5168 (4) 0.2065 (4) 0.2761 (4) 0.0399 (11)
C22 0.4711 (4) 0.3394 (4) 0.2034 (4) 0.0370 (10)
H22A 0.4316 0.3460 0.1356 0.044*
H22B 0.5493 0.3564 0.1802 0.044*
C23 0.1904 (4) 0.3957 (4) 0.2056 (4) 0.0339 (9)
C24 0.2531 (4) 0.4255 (4) 0.2824 (4) 0.0358 (10)
H24A 0.2734 0.3577 0.3545 0.043*
H24B 0.1902 0.5012 0.2957 0.043*
C25 0.3781 (4) 0.4452 (4) 0.2406 (4) 0.0345 (10)
C26 0.3477 (5) 0.5651 (4) 0.1416 (4) 0.0467 (12)
H26A 0.4297 0.5696 0.1105 0.056*
H26B 0.3001 0.5626 0.0833 0.056*
C27 0.2680 (6) 0.6817 (5) 0.1708 (5) 0.0621 (16)
H27A 0.2573 0.7552 0.1047 0.075*
H27B 0.1813 0.6832 0.1928 0.075*
C28 0.3328 (7) 0.6866 (5) 0.2655 (6) 0.0749 (19)
H28A 0.4142 0.6964 0.2400 0.090*
H28B 0.2759 0.7591 0.2867 0.090*
C29 0.3614 (6) 0.5711 (5) 0.3655 (5) 0.0641 (16)
H29A 0.2794 0.5664 0.3967 0.077*
H29B 0.4089 0.5746 0.4233 0.077*
C30 0.4424 (5) 0.4550 (5) 0.3339 (5) 0.0470 (12)
H30A 0.5275 0.4564 0.3098 0.056*
H30B 0.4568 0.3809 0.4003 0.056*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Ni1 0.0287 (4) 0.0311 (4) 0.0357 (5) -0.0073 (3) -0.0020 (3) -0.0160 (3)
Ni2 0.0286 (4) 0.0316 (4) 0.0318 (4) -0.0103 (3) 0.0000 (3) -0.0110 (3)
O1 0.0386 (18) 0.0320 (16) 0.0433 (18) -0.0119 (14) -0.0040 (14) -0.0109 (14)
O2 0.089 (3) 0.039 (2) 0.061 (3) -0.013 (2) 0.029 (2) -0.0156 (18)
O3 0.0363 (17) 0.0349 (16) 0.0367 (17) -0.0092 (14) -0.0103 (14) -0.0069 (14)
O4 0.062 (2) 0.0366 (17) 0.057 (2) -0.0164 (16) -0.0256 (19) -0.0087 (16)
N1 0.035 (2) 0.0311 (18) 0.035 (2) -0.0089 (16) -0.0046 (16) -0.0145 (16)
N2 0.0325 (19) 0.0350 (19) 0.0334 (19) -0.0113 (16) -0.0014 (16) -0.0133 (16)
N3 0.0341 (19) 0.0346 (19) 0.0314 (19) -0.0122 (16) -0.0023 (15) -0.0101 (16)
N4 0.0308 (19) 0.0352 (19) 0.035 (2) -0.0123 (16) 0.0005 (16) -0.0115 (16)
C1 0.032 (2) 0.039 (2) 0.039 (2) -0.0109 (19) 0.0034 (19) -0.017 (2)
C2 0.032 (2) 0.056 (3) 0.050 (3) -0.006 (2) 0.001 (2) -0.024 (3)
C3 0.029 (3) 0.066 (4) 0.070 (4) 0.000 (2) 0.005 (3) -0.024 (3)
C4 0.048 (3) 0.051 (3) 0.070 (4) 0.003 (3) 0.003 (3) -0.033 (3)
C5 0.048 (3) 0.052 (3) 0.050 (3) -0.010 (2) 0.003 (2) -0.027 (3)
C6 0.033 (2) 0.032 (2) 0.033 (2) -0.0058 (18) 0.0011 (19) -0.0126 (19)
C7 0.043 (3) 0.038 (2) 0.048 (3) -0.011 (2) -0.006 (2) -0.024 (2)
C8 0.047 (3) 0.043 (3) 0.047 (3) -0.015 (2) -0.006 (2) -0.024 (2)
C9 0.035 (2) 0.043 (3) 0.042 (3) -0.015 (2) -0.008 (2) -0.014 (2)
C10 0.058 (3) 0.053 (3) 0.071 (4) -0.030 (3) 0.006 (3) -0.030 (3)
C11 0.034 (2) 0.035 (2) 0.035 (2) -0.0128 (19) -0.0005 (19) -0.0085 (19)
C12 0.050 (3) 0.045 (3) 0.049 (3) -0.023 (2) 0.005 (2) -0.008 (2)
C13 0.062 (4) 0.043 (3) 0.062 (3) -0.027 (3) 0.002 (3) -0.008 (3)
C14 0.068 (4) 0.034 (3) 0.069 (4) -0.023 (3) 0.004 (3) -0.013 (3)
C15 0.049 (3) 0.040 (3) 0.051 (3) -0.016 (2) 0.004 (2) -0.014 (2)
C16 0.040 (2) 0.034 (2) 0.034 (2) -0.015 (2) -0.002 (2) -0.0070 (19)
C17 0.045 (3) 0.037 (2) 0.037 (2) -0.013 (2) 0.005 (2) -0.015 (2)
C18 0.033 (2) 0.041 (3) 0.046 (3) -0.008 (2) 0.009 (2) -0.017 (2)
C19 0.042 (3) 0.047 (3) 0.042 (3) -0.020 (2) 0.012 (2) -0.018 (2)
C20 0.066 (4) 0.053 (3) 0.039 (3) -0.020 (3) 0.008 (3) -0.021 (2)
C21 0.037 (2) 0.036 (2) 0.042 (3) -0.012 (2) 0.009 (2) -0.013 (2)
C22 0.035 (2) 0.037 (2) 0.037 (2) -0.0147 (19) 0.0039 (19) -0.009 (2)
C23 0.031 (2) 0.035 (2) 0.033 (2) -0.0124 (18) -0.0024 (18) -0.0081 (19)
C24 0.035 (2) 0.040 (2) 0.035 (2) -0.0146 (19) -0.0005 (19) -0.015 (2)
C25 0.032 (2) 0.029 (2) 0.040 (2) -0.0092 (18) -0.0044 (19) -0.0115 (19)
C26 0.046 (3) 0.038 (3) 0.053 (3) -0.018 (2) -0.004 (2) -0.008 (2)
C27 0.065 (4) 0.034 (3) 0.077 (4) -0.015 (3) -0.005 (3) -0.010 (3)
C28 0.082 (5) 0.051 (3) 0.105 (5) -0.025 (3) -0.013 (4 -0.040 (4)
C29 0.071 (4) 0.057 (3) 0.076 (4) -0.020 (3) -0.019 (3) -0.036 (3)
C30 0.039 (3) 0.042 (3) 0.058 (3) -0.011 (2) -0.015 (2) -0.015 (2)

Geometric parameters (Å, º)

Ni1—Ni2 8.0051 (6) C10—H10A 0.9800
Ni1—N1i 2.064 (3) C10—H10B 0.9800
Ni1—N1 2.064 (3) C10—H10C 0.9800
Ni1—N2i 2.097 (4) C11—C12 1.523 (6)
Ni1—N2 2.097 (4) C11—C16 1.542 (6)
Ni1—O1i 2.211 (3) C11—H11 1.0000
Ni1—O1 2.211 (3) C12—C13 1.531 (7)
Ni2—N3ii 2.054 (4) C12—H12A 0.9900
Ni2—N3 2.054 (4) C12—H12B 0.9900
Ni2—N4ii 2.096 (3) C13—C14 1.514 (8)
Ni2—N4 2.096 (3) C13—H13A 0.9900
Ni2—O3 2.150 (3) C13—H13B 0.9900
Ni2—O3ii 2.150 (3) C14—C15 1.515 (7)
O1—C21 1.271 (5) C14—H14A 0.9900
O2—C21 1.248 (6) C14—H14B 0.9900
O3—C23 1.264 (5) C15—C16 1.552 (6)
O4—C23 1.257 (5) C15—H15A 0.9900
N1—C7 1.460 (6) C15—H15B 0.9900
N1—C6 1.478 (6) C16—H16 1.0000
N1—HN1 0.9300 C17—C18ii 1.512 (7)
N2—C9 1.476 (6) C17—H17A 0.9900
N2—C1 1.483 (5) C17—H17B 0.9900
N2—HN2 0.9300 C18—C17ii 1.512 (7)
N3—C17 1.471 (6) C18—C19 1.559 (6)
N3—C16 1.486 (6) C18—H18A 0.9900
N3—HN3 0.9300 C18—H18B 0.9900
N4—C11 1.473 (5) C19—C20 1.493 (7)
N4—C19 1.489 (6) C19—H19 1.0000
N4—HN4 0.9300 C20—H20A 0.9800
C1—C2 1.529 (6) C20—H20B 0.9800
C1—C6i 1.531 (6) C20—H20C 0.9800
C1—H1 1.0000 C21—C22 1.503 (6)
C2—C3 1.513 (7) C22—C25 1.518 (6)
C2—H2A 0.9900 C22—H22A 0.9900
C2—H2B 0.9900 C22—H22B 0.9900
C3—C4i 1.541 (8) C23—C24 1.507 (6)
C3—H3A 0.9900 C24—C25 1.549 (6)
C3—H3B 0.9900 C24—H24A 0.9900
C4—C5 1.519 (7) C24—H24B 0.9900
C4—C3i 1.541 (8) C25—C26 1.535 (6)
C4—H4A 0.9900 C25—C30 1.539 (6)
C4—H4B 0.9900 C26—C27 1.531 (7)
C5—C6 1.526 (6) C26—H26A 0.9900
C5—H5A 0.9900 C26—H26B 0.9900
C5—H5B 0.9900 C27—C28 1.526 (9)
C6—C1i 1.531 (6) C27—H27A 0.9900
C6—H6 1.0000 C27—H27B 0.9900
C7—C8 1.503 (6) C28—C29 1.510 (9)
C7—H7A 0.9900 C28—H28A 0.9900
C7—H7B 0.9900 C28—H28B 0.9900
C8—C9 1.535 (7) C29—C30 1.544 (7)
C8—H8A 0.9900 C29—H29A 0.9900
C8—H8B 0.9900 C29—H29B 0.9900
C9—C10 1.509 (7) C30—H30A 0.9900
C9—H9 1.0000 C30—H30B 0.9900
N1i—Ni1—N1 180.00 (11) H10B—C10—H10C 109.5
N1i—Ni1—N2i 95.53 (14) N4—C11—C12 113.8 (4)
N1—Ni1—N2i 84.47 (14) N4—C11—C16 107.4 (3)
N1i—Ni1—N2 84.47 (14) C12—C11—C16 110.7 (4)
N1—Ni1—N2 95.53 (14) N4—C11—H11 108.3
N2i—Ni1—N2 180.0 C12—C11—H11 108.3
N1i—Ni1—O1i 91.22 (13) C16—C11—H11 108.3
N1—Ni1—O1i 88.78 (13) C11—C12—C13 111.9 (4)
N2i—Ni1—O1i 82.63 (13) C11—C12—H12A 109.2
N2—Ni1—O1i 97.37 (13) C13—C12—H12A 109.2
N1i—Ni1—O1 88.78 (13) C11—C12—H12B 109.2
N1—Ni1—O1 91.22 (13) C13—C12—H12B 109.2
N2i—Ni1—O1 97.37 (13) H12A—C12—H12B 107.9
N2—Ni1—O1 82.63 (13) C14—C13—C12 111.0 (4)
O1i—Ni1—O1 180.0 C14—C13—H13A 109.4
N3ii—Ni2—N3 180.0 (2) C12—C13—H13A 109.4
N3ii—Ni2—N4ii 83.97 (14) C14—C13—H13B 109.4
N3—Ni2—N4ii 96.03 (14) C12—C13—H13B 109.4
N3ii—Ni2—N4 96.03 (14) H13A—C13—H13B 108.0
N3—Ni2—N4 83.97 (14) C13—C14—C15 110.8 (5)
N4ii—Ni2—N4 180.0 C13—C14—H14A 109.5
N3ii—Ni2—O3 88.03 (13) C15—C14—H14A 109.5
N3—Ni2—O3 91.97 (13) C13—C14—H14B 109.5
N4ii—Ni2—O3 82.06 (13) C15—C14—H14B 109.5
N4—Ni2—O3 97.94 (13) H14A—C14—H14B 108.1
N3ii—Ni2—O3ii 91.97 (13) C14—C15—C16 111.8 (4)
N3—Ni2—O3ii 88.03 (13) C14—C15—H15A 109.3
N4ii—Ni2—O3ii 97.94 (13) C16—C15—H15A 109.3
N4—Ni2—O3ii 82.06 (13) C14—C15—H15B 109.3
O3—Ni2—O3ii 180.0 C16—C15—H15B 109.3
C21—O1—Ni1 130.8 (3) H15A—C15—H15B 107.9
C23—O3—Ni2 133.4 (3) N3—C16—C11 107.9 (4)
C7—N1—C6 115.3 (3) N3—C16—C15 113.7 (4)
C7—N1—Ni1 114.8 (3) C11—C16—C15 110.2 (4)
C6—N1—Ni1 107.9 (3) N3—C16—H16 108.3
C7—N1—HN1 106.0 C11—C16—H16 108.3
C6—N1—HN1 106.0 C15—C16—H16 108.3
Ni1—N1—HN1 106.0 N3—C17—C18ii 111.8 (4)
C9—N2—C1 116.4 (3) N3—C17—H17A 109.3
C9—N2—Ni1 119.6 (3) C18ii—C17—H17A 109.3
C1—N2—Ni1 106.8 (3) N3—C17—H17B 109.3
C9—N2—HN2 104.0 C18ii—C17—H17B 109.3
C1—N2—HN2 104.0 H17A—C17—H17B 107.9
Ni1—N2—HN2 104.0 C17ii—C18—C19 117.4 (4)
C17—N3—C16 114.6 (3) C17ii—C18—H18A 108.0
C17—N3—Ni2 114.8 (3) C19—C18—H18A 108.0
C16—N3—Ni2 107.1 (3) C17ii—C18—H18B 108.0
C17—N3—HN3 106.6 C19—C18—H18B 108.0
C16—N3—HN3 106.6 H18A—C18—H18B 107.2
Ni2—N3—HN3 106.6 N4—C19—C20 112.3 (4)
C11—N4—C19 117.1 (3) N4—C19—C18 108.7 (4)
C11—N4—Ni2 108.0 (3) C20—C19—C18 113.4 (4)
C19—N4—Ni2 120.9 (3) N4—C19—H19 107.4
C11—N4—HN4 102.6 C20—C19—H19 107.4
C19—N4—HN4 102.6 C18—C19—H19 107.4
Ni2—N4—HN4 102.6 C19—C20—H20A 109.5
N2—C1—C2 112.9 (4) C19—C20—H20B 109.5
N2—C1—C6i 109.3 (3) H20A—C20—H20B 109.5
C2—C1—C6i 102.6 C19—C20—H20A 109.5
N2—C1—H1 112.9 (4) C19—C20—H20B 109.5
C2—C1—H1 107.9 H20B—C20—H20C 109.5
C6i—C1—H1 107.9 O2—C21—O1 123.4 (4)
C3—C2—C1 111.9 (4) O2—C21—C22 116.0 (4)
C3—C2—H2A 109.2 O1—C21—C22 120.6 (4)
C1—C2—H2A 109.2 C21—C22—C25 123.4 (4)
C3—C2—H2B 109.2 C21—C22—H22A 106.5
C1—C2—H2B 109.2 C25—C22—H22A 106.5
H2A—C2—H2B 107.9 C21—C22—H22B 106.5
C2—C3—C4i 111.2 (5) C25—C22—H22B 106.5
C2—C3—H3A 109.4 H22A—C22—H22B 106.5
C4i—C3—H3A 109.4 O4—C23—O3 125.5 (4)
C2—C3—H3B 109.4 O4—C23—C24 117.4 (4)
C4i—C3—H3B 109.4 O3—C23—C24 117.1 (4)
H3A—C3—H3B 108.0 C23—C24—C25 115.5 (4)
C5—C4—C3i 110.8 (4) C23—C24—H24A 108.4
C5—C4—H4A 109.5 C25—C24—H24A 108.4
C3i—C4—H4A 109.5 C23—C24—H24B 108.4
C5—C4—H4B 109.5 C25—C24—H24B 108.4
C3i—C4—H4B 109.5 H24A—C24—H24B 107.5
H4A—C4—H4B 108.1 C22—C25—C26 108.0 (4)
C4—C5—C6 111.4 (4) C22—C25—C30 109.7 (4)
C4—C5—H5A 109.4 C26—C25—C30 108.0 (4)
C6—C5—H5A 109.4 C22—C25—C24 110.7 (3)
C4—C5—H5B 109.4 C26—C25—C24 110.6 (4)
C6—C5—H5B 109.4 C30—C25—C24 109.7 (4)
H5A—C5—H5B 108.0 C27—C26—C25 113.8 (5)
N1—C6—C5 113.4 (4) C27—C26—H26A 108.8
N1—C6—C1i 108.5 (3) C25—C26—H26A 108.8
C5—C6—C1i 110.3 (4) C27—C26—H26B 108.8
N1—C6—H6 108.2 C25—C26—H26B 108.8
C5—C6—H6 108.2 H26A—C26—H26B 107.7
C1i—C6—H6 108.2 C28—C27—C26 111.2 (5)
N1—C7—C8 111.5 (4) C28—C27—H27A 109.4
N1—C7—H7A 109.3 C26—C27—H27A 109.4
C8—C7—H7A 109.3 C28—C27—H27B 109.4
N1—C7—H7B 109.3 C26—C27—H27B 109.4
C8—C7—H7B 109.3 H27A—C27—H27B 108.0
H7A—C7—H7B 108.0 C29—C28—C27 111.5 (5)
C7—C8—C9 118.4 (4) C29—C28—H28A 109.3
C7—C8—H8A 107.7 C27—C28—H28A 109.3
C9—C8—H8A 107.7 C29—C28—H28B 109.3
C7—C8—H8B 107.7 C27—C28—H28B 109.3
C9—C8—H8B 107.7 H28A—C28—H28B 108.0
H8A—C8—H8B 107.1 C28—C29—C30 110.9 (5)
N2—C9—C10 112.9 (4) C28—C29—H29A 109.5
N2—C9—C8 108.5 (4) C30—C29—H29A 109.5
C10—C9—C8 112.7 (4) C28—C29—H29B 109.5
N2—C9—H9 107.5 C30—C29—H29B 109.5
C10—C9—H9 107.5 H29A—C29—H29B 108.1
C8—C9—H9 107.5 C25—C30—C29 113.0 (4)
C9—C10—H10A 109.5 C25—C30—H30A 109.0
C9—C10—H10B 109.5 C29—C30—H30A 109.0
H10A—C10—H10B 109.5 C25—C30—H30B 109.0
C9—C10—H10C 109.5 C29—C30—H30B 109.0
H10A—C10—H10C 109.5 H30A—C30—H30B 107.8
N1i—Ni1—O1—C21 -175.1 (4) C4—C5—C6—N1 179.3 (4)
N1—Ni1—O1—C21 4.9 (4) C4—C5—C6—C1i 57.4 (6)
N2i—Ni1—O1—C21 89.5 (4) C6—N1—C7—C8 -177.3 (4)
N2—Ni1—O1—C21 -90.5 (4) Ni1—N1—C7—C8 56.3 (5)
O1i—Ni1—O1—C21 0 (100) N1—C7—C8—C9 -77.5 (6)
N3ii—Ni2—O3—C23 170.9 (4) C1—N2—C9—C10 -52.6 (5)
N3—Ni2—O3—C23 -9.1 (4) Ni1—N2—C9—C10 78.3 (4)
N4ii—Ni2—O3—C23 -104.9 (4) C1—N2—C9—C8 -178.2 (4)
N4—Ni2—O3—C23 75.1 (4) Ni1—N2—C9—C -47.4 (4)
O3ii—Ni2—O3—C23 -157.5 (4) C7—C8—C9—N2 70.0 (5)
N1i—Ni1—N1—C7 -172 (100) C7—C8—C9—C10 -55.8 (6)
N2i—Ni1—N1—C7 145.6 (3) C19—N4—C11—C12 57.7 (5)
N2—Ni1—N1—C7 -34.4 (3) Ni2—N4—C11—C12 -161.7 (3)
O1i—Ni1—N1—C7 62.8 (3) C19—N4—C11—C16 -179.4 (4)
O1—Ni1—N1—C7 -117.2 (3) Ni2—N4—C11—C16 -38.8 (4)
N1i—Ni1—N1—C6 58 (100) N4—C11—C12—C13 176.6 (4)
N2i—Ni1—N1—C6 15.5 (3) C16—C11—C12—C13 55.6 (6)
N2—Ni1—N1—C6 -164.5 (3 C11—C12—C13—C14 -56.6 (6)
O1i—Ni1—N1—C6 -67.2 (3) C12—C13—C14—C15 56.6 (7)
O1—Ni1—N1—C6 112.8 (3) C13—C14—C15—C16 -56.7 (6)
N1i—Ni1—N2—C9 -148.0 (3) C17—N3—C16—C11 -173.1 (4)
N1—Ni1—N2—C9 32.0 (3) Ni2—N3—C16—C11 -44.5 (4)
N2i—Ni1—N2—C9 169 (100) C17—N3—C16—C15 64.4 (5)
O1i—Ni1—N2—C9 -57.4 (3) Ni2—N3—C16—C15 -167.0 (3)
O1—Ni1—N2—C9 122.6 (3) N4—C11—C16—N3 56.3 (5)
N1i—Ni1—N2—C1 -13.0 (3) C12—C11—C16—N3 -179.0 (4)
N1—Ni1—N2—C1 167.0 (3) N4—C11—C16—C15 -179.1 (4)
N2i—Ni1—N2—C1 -56 (100) C12—C11—C16—C15 -54.3 (5)
O1i—Ni1—N2—C1 77.5 (3) C14—C15—C16—N3 176.7 (4)
O1—Ni1—N2—C1 -102.5 (3) C14—C15—C16—C11 55.5 (6)
N3ii—Ni2—N3—C17 -73 (100) C16—N3—C17—C18ii -177.9 (4)
N4ii—Ni2—N3—C17 -33.2 (3) Ni2—N3—C17—C18ii 57.4 (5)
N4—Ni2—N3—C17 146.8 (3) C11—N4—C19—C20 53.2 (5)
O3—Ni2—N3—C17 -115.5 (3) Ni2—N4—C19—C20 -82.1 (4)
O3ii—Ni2—N3—C17 64.5 (3) C11—N4—C19—C18 179.5 (4)
N3ii—Ni2—N3—C16 159 (100) Ni2—N4—C19—C18 44.3 (5)
N4ii—Ni2—N3—C16 -161.7 (3) C17ii—C18—C19—N4 -68.0 (5)
N4—Ni2—N3—C16 18.3 (3) C17ii—C18—C19—C20 57.8 (6)
O3—Ni2—N3—C16 116.1 (3) Ni1—O1—C21—O2 -17.5 (7)
O3ii—Ni2—N3—C16 -63.9 (3) Ni1—O1—C21—C22 163.6 (3)
N3ii—Ni2—N4—C11 -168.0 (3) O2—C21—C22—C25 171.8 (5)
N3—Ni2—N4—C11 12.0 (3) O1—C21—C22—C25 -9.2 (7)
N4ii—Ni2—N4—C11 0 (100) Ni2—O3—C23—O4 -6.3 (7)
O3—Ni2—N4—C11 -79.1 (3) Ni2—O3—C23—C24 174.6 (3)
O3ii—Ni2—N4—C11 100.9 (3) O4—C23—C24—C25 90.5 (5)
N3ii—Ni2—N4—C19 -29.2 (3) O3—C23—C24—C25 -90.3 (5)
N3—Ni2—N4—C19 150.8 (3) C21—C22—C25—C26 -176.2 (4)
N4ii—Ni2—N4—C19 0 (100) C21—C22—C25—C30 66.3 (6)
O3—Ni2—N4—C19 59.7 (3) C21—C22—C25—C24 -54.9 (6)
O3ii—Ni2—N4—C19 -120.3 (3) C23—C24—C25—C22 -50.2 (5)
C9—N2—C1—C2 -60.9 (5) C23—C24—C25—C26 69.5 (5)
Ni1—N2—C1—C2 162.4 (3) C23—C24—C25—C30 -171.4 (4)
C9—N2—C1—C6i 175.2 (4) C22—C25—C26—C27 -172.7 (4)
Ni1—N2—C1—C6i 38.6 (4) C30—C25—C26—C27 -54.1 (6)
N2—C1—C2—C3 -178.6 (4) C24—C25—C26—C27 66.0 (6)
C6i—C1—C2—C3 -55.6 (6) C25—C26—C27—C2 55.1 (6)
C1—C2—C3—C4i 54.6 (6) C26—C27—C28—C29 -54.3 (7)
C3i—C4—C5—C6 -56.5 (6) C27—C28—C29—C30 55.1 (7)
C7—N1—C6—C5 66.7 (5) C22—C25—C30—C29 172.1 (5)
Ni1—N1—C6—C5 -163.5 (3) C26—C25—C30—C29 54.6 (6)
C7—N1—C6—C1i -170.4 (4) C24—C25—C30—C29 -66.1 (6)
Ni1—N1—C6—C1i -40.6 (4) C28—C29—C30—C25 -56.6 (7)

Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z.

Hydrogen-bond geometry (Å, º)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—HN1⋯O2 0.93 1.91 2.785 (5) 157
N2—HN2⋯O4 0.93 2.26 3.127 (5) 156
N3—HN3⋯O4 0.93 2.03 2.888 (5) 153