metal-organic compounds
In the title complex, [Ni(C11H12N3O2)(C2H3O2)(C5H5N)2], the NiII atom exhibits a distorted octahedral geometry, with two N atoms and one O atom of a tridentate butane-2,3-dione monooxime benzoylhydrazone ligand and one acetate O atom in the equatorial plane, and two pyridine N atoms in the axial sites. The uncoordinated acetate O atom forms an intramolecular hydrogen bond with the oxime O atom of the hydrazone ligand, with an OO distance and an O—HO angle of 2.541 (4) Å and 176 (5)°, respectively.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022767/cv6375sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022767/cv6375Isup2.hkl |
CCDC reference: 252778
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.087
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C2 .. 8.41 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.33 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C13 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C23
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 4892 Count of symmetry unique reflns 2765 Completeness (_total/calc) 176.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2127 Fraction of Friedel pairs measured 0.769 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Ni(C11H12N3O2)(C2H3O2)(C5H5N)2] | F(000) = 1032 |
Mr = 494.17 | Dx = 1.364 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 10153 reflections |
a = 12.378 (1) Å | θ = 3.1–27.5° |
b = 14.770 (1) Å | µ = 0.84 mm−1 |
c = 13.3291 (7) Å | T = 293 K |
β = 99.073 (4)° | Prism, green |
V = 2406.4 (3) Å3 | 0.38 × 0.25 × 0.18 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4892 independent reflections |
Radiation source: fine-focus sealed tube | 4039 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scan | h = −14→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −19→19 |
Tmin = 0.739, Tmax = 0.863 | l = −17→17 |
11139 measured reflections |
Refinement top
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.1684P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4892 reflections | Δρmax = 0.31 e Å−3 |
304 parameters | Δρmin = −0.20 e Å−3 |
3 restraints | Absolute structure: Friedel pairs were 2313. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (1) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.62258 (3) | 0.18061 (2) | 0.48281 (3) | 0.0600 (1) | |
N1 | 0.5839 (2) | 0.0438 (2) | 0.4523 (2) | 0.0716 (7) | |
N2 | 0.5550 (3) | 0.1803 (2) | 0.3378 (3) | 0.0605 (7) | |
N3 | 0.5559 (2) | 0.2596 (2) | 0.2831 (2) | 0.0643 (6) | |
N4 | 0.4661 (2) | 0.2048 (2) | 0.5312 (2) | 0.0654 (6) | |
N5 | 0.7831 (2) | 0.1655 (2) | 0.4464 (2) | 0.0644 (7) | |
O1 | 0.6336 (2) | 0.3174 (1) | 0.4412 (2) | 0.0658 (5) | |
O2 | 0.6055 (2) | −0.0292 (2) | 0.5168 (2) | 0.0871 (7) | |
O3 | 0.6904 (2) | 0.1899 (2) | 0.6306 (2) | 0.0745 (8) | |
O4 | 0.7069 (3) | 0.0449 (2) | 0.6764 (2) | 0.1043 (8) | |
C1 | 0.4915 (4) | −0.0656 (2) | 0.3296 (3) | 0.095 (1) | |
C2 | 0.5306 (3) | 0.0269 (2) | 0.3627 (2) | 0.0683 (7) | |
C3 | 0.5141 (3) | 0.1066 (2) | 0.2961 (2) | 0.0652 (8) | |
C4 | 0.4571 (3) | 0.1011 (3) | 0.1890 (2) | 0.087 (1) | |
C5 | 0.6018 (2) | 0.3241 (2) | 0.3449 (2) | 0.0610 (7) | |
C6 | 0.6176 (3) | 0.4124 (2) | 0.2952 (2) | 0.0634 (7) | |
C7 | 0.5670 (3) | 0.4308 (2) | 0.1956 (3) | 0.079 (1) | |
C8 | 0.5880 (4) | 0.5109 (3) | 0.1493 (3) | 0.091 (1) | |
C9 | 0.6577 (4) | 0.5739 (3) | 0.2006 (4) | 0.097 (1) | |
C10 | 0.7073 (4) | 0.5570 (3) | 0.2978 (4) | 0.094 (1) | |
C11 | 0.6871 (3) | 0.4773 (2) | 0.3466 (3) | 0.0754 (9) | |
C12 | 0.4335 (3) | 0.2880 (3) | 0.5449 (4) | 0.097 (1) | |
C13 | 0.3403 (4) | 0.3088 (3) | 0.5856 (4) | 0.113 (2) | |
C14 | 0.2774 (3) | 0.2398 (3) | 0.6119 (3) | 0.096 (1) | |
C15 | 0.3080 (4) | 0.1552 (4) | 0.5951 (4) | 0.113 (2) | |
C16 | 0.4025 (3) | 0.1393 (3) | 0.5551 (3) | 0.099 (1) | |
C17 | 0.8585 (3) | 0.2223 (3) | 0.4894 (3) | 0.0782 (8) | |
C18 | 0.9647 (3) | 0.2231 (3) | 0.4710 (3) | 0.090 (1) | |
C19 | 0.9938 (4) | 0.1645 (3) | 0.4051 (4) | 0.108 (1) | |
C20 | 0.9175 (4) | 0.1054 (3) | 0.3565 (4) | 0.117 (2) | |
C21 | 0.8116 (3) | 0.1067 (3) | 0.3794 (3) | 0.0855 (9) | |
C22 | 0.7795 (4) | 0.1580 (3) | 0.7968 (3) | 0.104 (1) | |
C23 | 0.7206 (3) | 0.1276 (3) | 0.6926 (3) | 0.0759 (9) | |
H1A | 0.4811 | −0.1007 | 0.3879 | 0.143* | |
H1B | 0.5448 | −0.0946 | 0.2954 | 0.143* | |
H1C | 0.4234 | −0.0610 | 0.2841 | 0.143* | |
H4A | 0.4206 | 0.1573 | 0.1703 | 0.131* | |
H4B | 0.4043 | 0.0529 | 0.1830 | 0.131* | |
H4C | 0.5096 | 0.0893 | 0.1448 | 0.131* | |
H7 | 0.5192 | 0.3888 | 0.1607 | 0.094* | |
H8 | 0.5548 | 0.5224 | 0.0830 | 0.109* | |
H9 | 0.6711 | 0.6280 | 0.1691 | 0.116* | |
H10 | 0.7551 | 0.5995 | 0.3317 | 0.113* | |
H11 | 0.7198 | 0.4671 | 0.4133 | 0.091* | |
H12 | 0.4754 | 0.3356 | 0.5262 | 0.117* | |
H13 | 0.3210 | 0.3687 | 0.5947 | 0.135* | |
H14 | 0.2151 | 0.2513 | 0.6408 | 0.115* | |
H15 | 0.2654 | 0.1068 | 0.6105 | 0.136* | |
H16 | 0.4221 | 0.0797 | 0.5444 | 0.118* | |
H17 | 0.8387 | 0.2644 | 0.5350 | 0.094* | |
H18 | 1.0151 | 0.2641 | 0.5043 | 0.107* | |
H19 | 1.0654 | 0.1634 | 0.3919 | 0.129* | |
H20 | 0.9363 | 0.0648 | 0.3087 | 0.140* | |
H21 | 0.7600 | 0.0660 | 0.3475 | 0.103* | |
H22A | 0.8177 | 0.1075 | 0.8312 | 0.155* | |
H22B | 0.7269 | 0.1805 | 0.8364 | 0.155* | |
H22C | 0.8308 | 0.2050 | 0.7882 | 0.155* | |
H24 | 0.643 (4) | −0.005 (3) | 0.570 (2) | 0.131* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0604 (2) | 0.0583 (2) | 0.0646 (2) | 0.0071 (2) | 0.0202 (1) | 0.0065 (2) |
N1 | 0.075 (2) | 0.058 (1) | 0.089 (2) | 0.007 (1) | 0.033 (1) | 0.015 (1) |
N2 | 0.059 (2) | 0.058 (2) | 0.068 (2) | 0.003 (1) | 0.020 (1) | 0.003 (1) |
N3 | 0.066 (2) | 0.064 (1) | 0.067 (1) | 0.010 (1) | 0.021 (1) | 0.008 (1) |
N4 | 0.055 (2) | 0.074 (2) | 0.070 (2) | 0.006 (1) | 0.017 (1) | 0.005 (1) |
N5 | 0.064 (2) | 0.062 (1) | 0.070 (2) | 0.008 (1) | 0.022 (1) | 0.003 (1) |
O1 | 0.073 (1) | 0.061 (1) | 0.067 (1) | 0.0068 (9) | 0.022 (1) | 0.0046 (8) |
O2 | 0.101 (2) | 0.065 (1) | 0.099 (2) | 0.006 (1) | 0.028 (1) | 0.023 (1) |
O3 | 0.071 (2) | 0.086 (2) | 0.069 (2) | 0.013 (1) | 0.019 (1) | 0.0089 (1) |
O4 | 0.123 (2) | 0.089 (2) | 0.094 (2) | 0.003 (2) | −0.003 (2) | 0.028 (1) |
C1 | 0.104 (3) | 0.072 (2) | 0.112 (3) | −0.013 (2) | 0.026 (2) | −0.004 (2) |
C2 | 0.069 (2) | 0.067 (2) | 0.074 (2) | −0.003 (1) | 0.027 (2) | −0.001 (1) |
C3 | 0.058 (2) | 0.070 (2) | 0.073 (2) | 0.001 (1) | 0.026 (1) | −0.002 (2) |
C4 | 0.091 (3) | 0.096 (2) | 0.075 (2) | −0.004 (2) | 0.013 (2) | −0.004 (2) |
C5 | 0.058 (2) | 0.063 (2) | 0.067 (2) | 0.015 (1) | 0.024 (1) | 0.009 (1) |
C6 | 0.064 (2) | 0.061 (2) | 0.071 (2) | 0.011 (1) | 0.028 (1) | 0.007 (1) |
C7 | 0.088 (2) | 0.067 (2) | 0.086 (2) | 0.018 (2) | 0.030 (2) | 0.011 (2) |
C8 | 0.107 (3) | 0.083 (2) | 0.086 (2) | 0.018 (2) | 0.028 (2) | 0.025 (2) |
C9 | 0.102 (3) | 0.075 (2) | 0.123 (4) | 0.020 (2) | 0.051 (3) | 0.039 (2) |
C10 | 0.085 (3) | 0.072 (2) | 0.133 (3) | −0.006 (2) | 0.042 (2) | 0.011 (2) |
C11 | 0.066 (2) | 0.071 (2) | 0.093 (2) | 0.006 (2) | 0.028 (2) | 0.011 (2) |
C12 | 0.078 (3) | 0.089 (2) | 0.135 (3) | −0.007 (2) | 0.046 (2) | −0.026 (2) |
C13 | 0.089 (3) | 0.104 (3) | 0.156 (4) | 0.010 (2) | 0.053 (3) | −0.033 (3) |
C14 | 0.067 (2) | 0.139 (4) | 0.085 (2) | 0.014 (2) | 0.027 (2) | 0.002 (2) |
C15 | 0.088 (3) | 0.114 (3) | 0.153 (5) | 0.006 (3) | 0.064 (3) | 0.028 (3) |
C16 | 0.090 (3) | 0.086 (2) | 0.132 (3) | 0.015 (2) | 0.055 (3) | 0.026 (2) |
C17 | 0.069 (2) | 0.089 (2) | 0.079 (2) | 0.004 (2) | 0.018 (2) | −0.007 (2) |
C18 | 0.057 (2) | 0.107 (3) | 0.106 (2) | 0.002 (2) | 0.016 (2) | 0.004 (2) |
C19 | 0.066 (3) | 0.131 (4) | 0.133 (4) | 0.005 (2) | 0.038 (2) | −0.013 (3) |
C20 | 0.105 (3) | 0.120 (4) | 0.140 (4) | 0.016 (3) | 0.062 (3) | −0.034 (3) |
C21 | 0.081 (2) | 0.080 (2) | 0.103 (2) | 0.008 (2) | 0.035 (2) | −0.013 (2) |
C22 | 0.097 (3) | 0.120 (3) | 0.087 (2) | −0.021 (2) | −0.005 (2) | 0.028 (2) |
C23 | 0.065 (2) | 0.088 (2) | 0.077 (2) | 0.004 (2) | 0.018 (2) | 0.019 (2) |
Geometric parameters (Å, º) top
Ni1—N1 | 2.102 (2) | C7—C8 | 1.378 (5) |
Ni1—N2 | 1.982 (3) | C7—H7 | 0.9300 |
Ni1—N5 | 2.130 (3) | C8—C9 | 1.375 (7) |
Ni1—N4 | 2.165 (3) | C8—H8 | 0.9300 |
Ni1—O1 | 2.106 (2) | C9—C10 | 1.367 (6) |
Ni1—O3 | 2.020 (3) | C9—H9 | 0.9300 |
N2—N3 | 1.380 (3) | C10—C11 | 1.387 (5) |
C2—C3 | 1.469 (4) | C10—H10 | 0.9300 |
N1—C2 | 1.294 (4) | C11—H11 | 0.9300 |
N2—C3 | 1.288 (4) | C12—C13 | 1.384 (5) |
N3—C5 | 1.328 (4) | C12—H12 | 0.9300 |
O1—C5 | 1.286 (4) | C13—C14 | 1.361 (6) |
N4—C12 | 1.315 (5) | C13—H13 | 0.9300 |
N4—C16 | 1.319 (5) | C14—C15 | 1.335 (7) |
N5—C17 | 1.317 (5) | C14—H14 | 0.9300 |
N5—C21 | 1.332 (4) | C15—C16 | 1.381 (5) |
O2—N1 | 1.378 (3) | C15—H15 | 0.9300 |
O2—H24 | 0.86 (4) | C16—H16 | 0.9300 |
O3—C23 | 1.254 (4) | C17—C18 | 1.374 (5) |
O4—C23 | 1.246 (5) | C17—H17 | 0.9300 |
C1—C2 | 1.493 (5) | C18—C19 | 1.323 (6) |
C1—H1A | 0.9600 | C18—H18 | 0.9300 |
C1—H1B | 0.9600 | C19—C20 | 1.373 (7) |
C1—H1C | 0.9600 | C19—H19 | 0.9300 |
C3—C4 | 1.492 (5) | C20—C21 | 1.392 (6) |
C4—H4A | 0.9600 | C20—H20 | 0.9300 |
C4—H4B | 0.9600 | C21—H21 | 0.9300 |
C4—H4C | 0.9600 | C22—C23 | 1.531 (6) |
C5—C6 | 1.489 (4) | C22—H22A | 0.9600 |
C6—C7 | 1.402 (5) | C22—H22B | 0.9600 |
C6—C11 | 1.393 (5) | C22—H22C | 0.9600 |
N1—Ni1—N4 | 91.7 (1) | C8—C7—H7 | 119.9 |
N1—Ni1—N5 | 92.7 (1) | C8—C9—H9 | 120.0 |
N1—Ni1—O1 | 153.4 (1) | C9—C8—C7 | 120.4 (4) |
N2—Ni1—N1 | 76.2 (1) | C9—C8—H8 | 119.8 |
N2—Ni1—N4 | 91.8 (1) | C9—C10—C11 | 120.8 (4) |
N2—Ni1—N5 | 92.5 (1) | C9—C10—H10 | 119.6 |
N2—Ni1—O1 | 77.28 (9) | C10—C9—C8 | 120.0 (3) |
N2—Ni1—O3 | 176.21 (9) | C10—C9—H9 | 120.0 |
N5—Ni1—N4 | 174.5 (1) | C10—C11—C6 | 119.7 (4) |
O1—Ni1—N4 | 91.04 (9) | C10—C11—H11 | 120.1 |
O1—Ni1—N5 | 86.51 (9) | C11—C6—C5 | 119.8 (3) |
O3—Ni1—N1 | 107.5 (1) | C11—C6—C7 | 118.8 (3) |
O3—Ni1—N4 | 87.2 (1) | C11—C10—H10 | 119.6 |
O3—Ni1—N5 | 88.3 (1) | C12—N4—Ni1 | 120.3 (2) |
O3—Ni1—O1 | 99.06 (9) | C12—N4—C16 | 116.4 (3) |
N1—O2—H24 | 103 (4) | C12—C13—H13 | 120.6 |
N1—C2—C1 | 122.9 (3) | C13—C12—H12 | 118.2 |
N1—C2—C3 | 113.9 (3) | C13—C14—H14 | 121.0 |
N2—C3—C2 | 114.1 (3) | C14—C13—C12 | 118.8 (4) |
N2—C3—C4 | 123.6 (3) | C14—C13—H13 | 120.6 |
N3—N2—Ni1 | 118.4 (2) | C14—C15—C16 | 120.3 (5) |
N3—C5—C6 | 115.3 (3) | C14—C15—H15 | 119.9 |
N4—C12—C13 | 123.7 (4) | C15—C14—C13 | 117.9 (4) |
N4—C12—H12 | 118.2 | C15—C14—H14 | 121.0 |
N4—C16—C15 | 122.9 (4) | C15—C16—H16 | 118.6 |
N4—C16—H16 | 118.6 | C16—N4—Ni1 | 123.2 (3) |
N5—C17—C18 | 124.1 (3) | C16—C15—H15 | 119.9 |
N5—C17—H17 | 118.0 | C17—N5—Ni1 | 117.2 (2) |
N5—C21—C20 | 120.9 (4) | C17—N5—C21 | 117.5 (3) |
N5—C21—H21 | 119.5 | C17—C18—H18 | 120.6 |
O1—C5—N3 | 126.7 (2) | C18—C17—H17 | 118.0 |
O1—C5—C6 | 118.0 (3) | C18—C19—C20 | 119.4 (4) |
O2—N1—Ni1 | 127.9 (2) | C18—C19—H19 | 120.3 |
O3—C23—C22 | 115.6 (4) | C19—C18—C17 | 118.7 (4) |
O4—C23—O3 | 125.9 (4) | C19—C18—H18 | 120.6 |
O4—C23—C22 | 118.4 (3) | C19—C20—C21 | 119.3 (4) |
C2—N1—Ni1 | 115.5 (2) | C19—C20—H20 | 120.4 |
C2—N1—O2 | 116.5 (3) | C20—C19—H19 | 120.3 |
C2—C1—H1A | 109.5 | C20—C21—H21 | 119.5 |
C2—C1—H1B | 109.5 | C21—N5—Ni1 | 125.2 (3) |
C2—C1—H1C | 109.5 | C21—C20—H20 | 120.4 |
C2—C3—C4 | 122.2 (3) | C23—O3—Ni1 | 128.9 (3) |
C3—N2—Ni1 | 119.9 (2) | C23—C22—H22A | 109.5 |
C3—N2—N3 | 121.6 (3) | C23—C22—H22B | 109.5 |
C3—C2—C1 | 123.2 (3) | C23—C22—H22C | 109.5 |
C3—C4—H4A | 109.5 | H1A—C1—H1B | 109.5 |
C3—C4—H4B | 109.5 | H1A—C1—H1C | 109.5 |
C3—C4—H4C | 109.5 | H1B—C1—H1C | 109.5 |
C5—N3—N2 | 108.7 (2) | H4A—C4—H4B | 109.5 |
C5—O1—Ni1 | 108.3 (2) | H4A—C4—H4C | 109.5 |
C6—C7—H7 | 119.9 | H4B—C4—H4C | 109.5 |
C6—C11—H11 | 120.1 | H22A—C22—H22B | 109.5 |
C7—C6—C5 | 121.3 (3) | H22A—C22—H22C | 109.5 |
C7—C8—H8 | 119.8 | H22B—C22—H22C | 109.5 |
C8—C7—C6 | 120.2 (4) | ||
Ni1—N1—C2—C1 | −176.9 (3) | N5—Ni1—N2—C3 | 97.2 (3) |
Ni1—N1—C2—C3 | 4.3 (3) | N5—Ni1—O1—C5 | 86.9 (2) |
Ni1—N2—N3—C5 | −2.2 (3) | N5—Ni1—O3—C23 | −82.6 (3) |
Ni1—N2—C3—C2 | −4.3 (4) | N5—C17—C18—C19 | 1.0 (6) |
Ni1—N2—C3—C4 | 177.0 (2) | O1—Ni1—N1—O2 | 172.9 (2) |
Ni1—N4—C12—C13 | −173.1 (4) | O1—Ni1—N1—C2 | −9.2 (3) |
Ni1—N4—C16—C15 | 173.6 (4) | O1—Ni1—N2—N3 | 4.9 (2) |
Ni1—N5—C17—C18 | −177.8 (3) | O1—Ni1—N2—C3 | −176.9 (3) |
Ni1—N5—C21—C20 | 176.3 (3) | O1—Ni1—N4—C12 | −14.7 (3) |
Ni1—O1—C5—N3 | 8.4 (3) | O1—Ni1—N4—C16 | 170.0 (3) |
Ni1—O1—C5—C6 | −171.3 (2) | O1—Ni1—N5—C17 | 52.6 (3) |
Ni1—O3—C23—O4 | −5.8 (6) | O1—Ni1—N5—C21 | −123.4 (3) |
Ni1—O3—C23—C22 | 174.2 (3) | O1—Ni1—O3—C23 | −168.8 (3) |
N1—Ni1—N2—N3 | −173.2 (3) | O1—C5—C6—C7 | −167.6 (3) |
N1—Ni1—N2—C3 | 5.0 (2) | O1—C5—C6—C11 | 14.9 (4) |
N1—Ni1—N4—C12 | −168.2 (3) | O2—N1—C2—C1 | 1.3 (4) |
N1—Ni1—N4—C16 | 16.5 (3) | O2—N1—C2—C3 | −177.6 (2) |
N1—Ni1—N5—C17 | −154.1 (3) | O3—Ni1—N1—C2 | 174.1 (2) |
N1—Ni1—N5—C21 | 30.0 (3) | O3—Ni1—N1—O2 | −3.8 (3) |
N1—Ni1—O1—C5 | −2.2 (3) | O3—Ni1—N4—C12 | 84.4 (3) |
N1—Ni1—O3—C23 | 9.7 (4) | O3—Ni1—N4—C16 | −90.9 (3) |
N1—C2—C3—N2 | −0.2 (4) | O3—Ni1—N5—C17 | −46.6 (3) |
N1—C2—C3—C4 | 178.4 (3) | O3—Ni1—N5—C21 | 137.4 (3) |
N2—Ni1—N1—O2 | 177.1 (3) | O3—Ni1—O1—C5 | 174.6 (2) |
N2—Ni1—N1—C2 | −5.0 (2) | C1—C2—C3—N2 | −179.1 (3) |
N2—Ni1—N4—C12 | −92.0 (3) | C1—C2—C3—C4 | −0.4 (5) |
N2—Ni1—N4—C16 | 92.7 (3) | C3—N2—N3—C5 | 179.6 (3) |
N2—Ni1—N5—C17 | 129.7 (3) | C5—C6—C7—C8 | −176.2 (3) |
N2—Ni1—N5—C21 | −46.3 (3) | C5—C6—C11—C10 | 175.8 (3) |
N2—Ni1—O1—C5 | −6.42 (18) | C6—C7—C8—C9 | −0.6 (6) |
N2—N3—C5—O1 | −4.7 (4) | C7—C6—C11—C10 | −1.8 (5) |
N2—N3—C5—C6 | 175.0 (2) | C7—C8—C9—C10 | 0.4 (6) |
N3—N2—C3—C2 | 173.8 (3) | C8—C9—C10—C11 | −0.9 (6) |
N3—N2—C3—C4 | −4.8 (5) | C9—C10—C11—C6 | 1.6 (6) |
N3—C5—C6—C7 | 12.6 (4) | C11—C6—C7—C8 | 1.3 (5) |
N3—C5—C6—C11 | −164.9 (3) | C12—N4—C16—C15 | −1.9 (7) |
N4—Ni1—N1—C2 | 86.5 (2) | C12—C13—C14—C15 | −1.4 (7) |
N4—Ni1—N1—O2 | −91.5 (2) | C13—C14—C15—C16 | 1.9 (7) |
N4—Ni1—N2—N3 | 95.5 (2) | C14—C15—C16—N4 | −0.3 (8) |
N4—Ni1—N2—C3 | −86.3 (3) | C16—N4—C12—C13 | 2.5 (7) |
N4—Ni1—O1—C5 | −98.0 (2) | C17—N5—C21—C20 | 0.4 (6) |
N4—Ni1—O3—C23 | 100.6 (3) | C17—C18—C19—C20 | 0.6 (8) |
N4—C12—C13—C14 | −0.9 (8) | C18—C19—C20—C21 | −1.7 (8) |
N5—Ni1—N1—O2 | 85.2 (2) | C19—C20—C21—N5 | 1.2 (7) |
N5—Ni1—N1—C2 | −96.9 (2) | C21—N5—C17—C18 | −1.5 (5) |
N5—Ni1—N2—N3 | −81.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H24···O4 | 0.86 (4) | 1.68 (3) | 2.541 (4) | 176 (5) |