In the title compound, [Ni(C
4H
12N
2O)
2](C
4O
4)·H
2O or [Ni(Hydet-en)
2](Sq)·H
2O, where Hydet-en is
N-(2-hydroxyethyl)ethylenediamine and Sq is the squarate dianion, the Ni
II centre has a distorted octahedral coordination geometry comprising four amine N and two hydroxyl O atoms from two tridentate Hydet-en ligands. All the O atoms of the squarate dianion are involved in N—H
O and O—H
O hydrogen bonding.
Supporting information
CCDC reference: 293870
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.004 Å
- H-atom completeness 97%
- Disorder in solvent or counterion
- R factor = 0.042
- wR factor = 0.094
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O5 .. O7 .. 2.70 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact O6 .. O7 .. 2.63 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 10.00 Perc.
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C12 H26 N4 Ni1 O7
Atom count from the _atom_site data: C12 H25 N4 Ni1 O7
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C12 H26 N4 Ni O7
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 48.00 48.00 0.00
H 104.00 100.00 4.00
N 16.00 16.00 0.00
Ni 4.00 4.00 0.00
O 28.00 28.00 0.00
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis[
N-(2-hydroxyethyl)ethylenediamine-
κ3N,
N',
O]nickel(II) squarate monohydrate
top
Crystal data top
[Ni(C4H12N2O)2](C4O4)·H2O | F(000) = 840 |
Mr = 397.08 | Dx = 1.500 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5487 reflections |
a = 11.9740 (8) Å | θ = 2.3–28.0° |
b = 8.7618 (4) Å | µ = 1.14 mm−1 |
c = 16.9051 (12) Å | T = 297 K |
β = 97.454 (6)° | Prism, violet |
V = 1758.59 (19) Å3 | 0.30 × 0.28 × 0.16 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 4128 independent reflections |
Radiation source: fine-focus sealed tube | 3478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.8°, θmin = 2.4° |
ω scans | h = −15→15 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −11→11 |
Tmin = 0.659, Tmax = 0.763 | l = −22→22 |
28256 measured reflections | |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0321P)2 + 1.2308P] where P = (Fo2 + 2Fc2)/3 |
4128 reflections | (Δ/σ)max = 0.004 |
250 parameters | Δρmax = 0.48 e Å−3 |
3 restraints | Δρmin = −0.65 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.1482 (3) | 0.3552 (3) | 0.14839 (18) | 0.0505 (6) | |
H1A | 0.1396 | 0.3367 | 0.0914 | 0.061* | |
H1B | 0.1037 | 0.2801 | 0.1727 | 0.061* | |
C2 | 0.2709 (3) | 0.3417 (3) | 0.18295 (18) | 0.0528 (7) | |
H2A | 0.2790 | 0.3525 | 0.2405 | 0.063* | |
H2B | 0.3002 | 0.2427 | 0.1703 | 0.063* | |
C3 | 0.4475 (2) | 0.4920 (4) | 0.1870 (2) | 0.0629 (8) | |
H3A | 0.4953 | 0.4048 | 0.1804 | 0.076* | |
H3B | 0.4470 | 0.5094 | 0.2436 | 0.076* | |
C4 | 0.4911 (3) | 0.6302 (5) | 0.1490 (2) | 0.0747 (10) | |
H4A | 0.5627 | 0.6609 | 0.1782 | 0.090* | |
H4B | 0.5028 | 0.6072 | 0.0945 | 0.090* | |
C5 | 0.1261 (3) | 0.8248 (3) | 0.01590 (17) | 0.0536 (7) | |
H5A | 0.0492 | 0.7917 | 0.0176 | 0.064* | |
H5B | 0.1306 | 0.8708 | −0.0358 | 0.064* | |
C6 | 0.1595 (3) | 0.9401 (3) | 0.08124 (17) | 0.0535 (7) | |
H6A | 0.2341 | 0.9799 | 0.0770 | 0.064* | |
H6B | 0.1067 | 1.0246 | 0.0767 | 0.064* | |
C7 | 0.2093 (3) | 0.9424 (3) | 0.23007 (17) | 0.0517 (7) | |
H7A | 0.1633 | 1.0294 | 0.2405 | 0.062* | |
H7B | 0.2838 | 0.9790 | 0.2230 | 0.062* | |
C8 | 0.2168 (3) | 0.8323 (3) | 0.29851 (17) | 0.0558 (7) | |
H8A | 0.2570 | 0.8785 | 0.3461 | 0.067* | |
H8B | 0.1420 | 0.8046 | 0.3095 | 0.067* | |
C9 | 0.1494 (2) | 0.3266 (3) | 0.37272 (15) | 0.0458 (6) | |
C10 | 0.1670 (2) | 0.1909 (3) | 0.42371 (14) | 0.0400 (5) | |
C11 | 0.2775 (2) | 0.2510 (3) | 0.45657 (15) | 0.0441 (6) | |
C12 | 0.2595 (2) | 0.3832 (3) | 0.40525 (16) | 0.0472 (6) | |
N1 | 0.10912 (17) | 0.5102 (2) | 0.16446 (13) | 0.0407 (4) | |
H1C | 0.0908 | 0.5161 | 0.2144 | 0.049* | |
H1D | 0.0480 | 0.5343 | 0.1299 | 0.049* | |
N2 | 0.33288 (18) | 0.4630 (3) | 0.14809 (13) | 0.0425 (5) | |
N3 | 0.20283 (19) | 0.6935 (3) | 0.02770 (12) | 0.0437 (5) | |
H3C | 0.2661 | 0.7124 | 0.0059 | 0.052* | |
H3D | 0.1697 | 0.6099 | 0.0043 | 0.052* | |
N4 | 0.1586 (2) | 0.8623 (2) | 0.15808 (13) | 0.0402 (4) | |
O1 | 0.27553 (18) | 0.7001 (2) | 0.27665 (11) | 0.0496 (5) | |
O2 | 0.41059 (17) | 0.7518 (3) | 0.14956 (14) | 0.0570 (5) | |
O3 | 0.07164 (17) | 0.3762 (3) | 0.32267 (13) | 0.0711 (7) | |
O4 | 0.11124 (17) | 0.0759 (2) | 0.43492 (12) | 0.0553 (5) | |
O5 | 0.35550 (17) | 0.2085 (3) | 0.50836 (13) | 0.0664 (6) | |
O6 | 0.3149 (2) | 0.5016 (3) | 0.39384 (14) | 0.0715 (7) | |
O7 | 0.4344 (4) | 0.6832 (8) | 0.4959 (3) | 0.0913 (19) | 0.50 |
O8 | 0.5368 (4) | 0.5355 (6) | 0.4022 (3) | 0.0672 (13) | 0.50 |
H8C | 0.480 (4) | 0.517 (9) | 0.424 (4) | 0.10 (3)* | 0.50 |
H8D | 0.571 (5) | 0.609 (6) | 0.426 (4) | 0.08 (2)* | 0.50 |
Ni1 | 0.24129 (3) | 0.65868 (3) | 0.150954 (18) | 0.03395 (9) | |
H4 | 0.092 (3) | 0.842 (4) | 0.1614 (19) | 0.053 (9)* | |
H1 | 0.282 (3) | 0.628 (5) | 0.318 (2) | 0.079 (12)* | |
H2 | 0.421 (3) | 0.831 (5) | 0.121 (2) | 0.080 (13)* | |
H3 | 0.338 (2) | 0.440 (3) | 0.0999 (17) | 0.039 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0629 (17) | 0.0320 (12) | 0.0559 (16) | −0.0090 (12) | 0.0056 (13) | 0.0006 (11) |
C2 | 0.0663 (18) | 0.0365 (13) | 0.0555 (16) | 0.0102 (13) | 0.0067 (13) | 0.0065 (12) |
C3 | 0.0426 (15) | 0.070 (2) | 0.072 (2) | 0.0173 (14) | −0.0091 (13) | −0.0101 (16) |
C4 | 0.0363 (15) | 0.100 (3) | 0.087 (2) | −0.0009 (17) | 0.0070 (15) | −0.018 (2) |
C5 | 0.0635 (17) | 0.0514 (16) | 0.0426 (14) | −0.0022 (13) | −0.0056 (12) | 0.0148 (12) |
C6 | 0.0659 (18) | 0.0377 (13) | 0.0547 (16) | 0.0010 (12) | −0.0007 (13) | 0.0132 (12) |
C7 | 0.0701 (18) | 0.0333 (12) | 0.0509 (15) | 0.0027 (12) | 0.0052 (13) | −0.0068 (11) |
C8 | 0.076 (2) | 0.0487 (15) | 0.0438 (14) | 0.0080 (14) | 0.0105 (13) | −0.0056 (12) |
C9 | 0.0378 (12) | 0.0596 (16) | 0.0395 (12) | −0.0040 (11) | 0.0034 (10) | 0.0100 (11) |
C10 | 0.0382 (12) | 0.0449 (13) | 0.0369 (12) | −0.0021 (10) | 0.0048 (9) | 0.0004 (10) |
C11 | 0.0368 (12) | 0.0570 (16) | 0.0377 (12) | −0.0044 (11) | 0.0024 (9) | 0.0101 (11) |
C12 | 0.0428 (13) | 0.0545 (15) | 0.0427 (13) | −0.0097 (12) | −0.0004 (10) | 0.0103 (11) |
N1 | 0.0387 (10) | 0.0371 (10) | 0.0456 (11) | −0.0011 (8) | 0.0029 (8) | 0.0032 (8) |
N2 | 0.0425 (11) | 0.0436 (11) | 0.0404 (11) | 0.0070 (9) | 0.0015 (9) | −0.0044 (9) |
N3 | 0.0461 (12) | 0.0477 (12) | 0.0368 (10) | −0.0027 (9) | 0.0034 (9) | −0.0012 (9) |
N4 | 0.0431 (12) | 0.0301 (10) | 0.0467 (11) | 0.0014 (9) | 0.0036 (9) | 0.0045 (8) |
O1 | 0.0666 (13) | 0.0425 (10) | 0.0388 (9) | 0.0066 (9) | 0.0030 (8) | 0.0032 (8) |
O2 | 0.0466 (11) | 0.0615 (13) | 0.0627 (13) | −0.0134 (10) | 0.0064 (9) | 0.0026 (11) |
O3 | 0.0416 (10) | 0.1067 (19) | 0.0618 (13) | −0.0049 (11) | −0.0054 (9) | 0.0405 (13) |
O4 | 0.0489 (11) | 0.0507 (11) | 0.0636 (12) | −0.0129 (9) | −0.0021 (9) | 0.0069 (9) |
O5 | 0.0414 (10) | 0.0929 (16) | 0.0607 (12) | −0.0123 (11) | −0.0090 (9) | 0.0363 (12) |
O6 | 0.0632 (13) | 0.0741 (15) | 0.0714 (14) | −0.0289 (12) | −0.0130 (10) | 0.0310 (12) |
O7 | 0.053 (3) | 0.131 (5) | 0.093 (4) | −0.014 (3) | 0.019 (3) | −0.047 (4) |
O8 | 0.040 (2) | 0.074 (3) | 0.088 (3) | −0.007 (2) | 0.010 (2) | −0.039 (3) |
Ni1 | 0.03465 (15) | 0.03061 (14) | 0.03573 (15) | 0.00025 (12) | 0.00133 (10) | 0.00017 (12) |
Geometric parameters (Å, º) top
C1—N1 | 1.473 (3) | C8—H8A | 0.97 |
C1—C2 | 1.514 (4) | C8—H8B | 0.97 |
C1—H1A | 0.97 | C9—O3 | 1.252 (3) |
C1—H1B | 0.97 | C9—C12 | 1.449 (4) |
C2—N2 | 1.463 (4) | C9—C10 | 1.467 (4) |
C2—H2A | 0.97 | C10—O4 | 1.237 (3) |
C2—H2B | 0.97 | C10—C11 | 1.465 (3) |
C3—N2 | 1.465 (3) | C11—O5 | 1.251 (3) |
C3—C4 | 1.497 (5) | C11—C12 | 1.447 (4) |
C3—H3A | 0.97 | C12—O6 | 1.259 (3) |
C3—H3B | 0.97 | N1—Ni1 | 2.084 (2) |
C4—O2 | 1.438 (4) | N1—H1C | 0.90 |
C4—H4A | 0.97 | N1—H1D | 0.90 |
C4—H4B | 0.97 | N2—Ni1 | 2.039 (2) |
C5—N3 | 1.470 (4) | N2—H3 | 0.85 (3) |
C5—C6 | 1.512 (4) | N3—Ni1 | 2.097 (2) |
C5—H5A | 0.97 | N3—H3C | 0.90 |
C5—H5B | 0.97 | N3—H3D | 0.90 |
C6—N4 | 1.469 (3) | N4—Ni1 | 2.051 (2) |
C6—H6A | 0.97 | N4—H4 | 0.82 (3) |
C6—H6B | 0.97 | O1—Ni1 | 2.1422 (19) |
C7—N4 | 1.467 (3) | O1—H1 | 0.93 (4) |
C7—C8 | 1.500 (4) | O2—Ni1 | 2.188 (2) |
C7—H7A | 0.97 | O2—H2 | 0.87 (4) |
C7—H7B | 0.97 | O8—H8C | 0.836 (10) |
C8—O1 | 1.428 (3) | O8—H8D | 0.836 (10) |
| | | |
N1—C1—C2 | 108.4 (2) | C11—C10—C9 | 89.2 (2) |
N1—C1—H1A | 110.0 | O5—C11—C12 | 134.2 (2) |
C2—C1—H1A | 110.0 | O5—C11—C10 | 135.6 (3) |
N1—C1—H1B | 110.0 | C12—C11—C10 | 90.17 (19) |
C2—C1—H1B | 110.0 | O6—C12—C11 | 135.3 (2) |
H1A—C1—H1B | 108.4 | O6—C12—C9 | 134.1 (2) |
N2—C2—C1 | 107.8 (2) | C11—C12—C9 | 90.6 (2) |
N2—C2—H2A | 110.1 | C1—N1—Ni1 | 106.96 (16) |
C1—C2—H2A | 110.1 | C1—N1—H1C | 110.3 |
N2—C2—H2B | 110.1 | Ni1—N1—H1C | 110.3 |
C1—C2—H2B | 110.1 | C1—N1—H1D | 110.3 |
H2A—C2—H2B | 108.5 | Ni1—N1—H1D | 110.3 |
N2—C3—C4 | 107.8 (3) | H1C—N1—H1D | 108.6 |
N2—C3—H3A | 110.1 | C2—N2—C3 | 116.1 (2) |
C4—C3—H3A | 110.1 | C2—N2—Ni1 | 107.39 (17) |
N2—C3—H3B | 110.1 | C3—N2—Ni1 | 108.58 (18) |
C4—C3—H3B | 110.1 | C2—N2—H3 | 108.4 (19) |
H3A—C3—H3B | 108.5 | C3—N2—H3 | 107.1 (19) |
O2—C4—C3 | 109.0 (3) | Ni1—N2—H3 | 109.1 (19) |
O2—C4—H4A | 109.9 | C5—N3—Ni1 | 107.56 (16) |
C3—C4—H4A | 109.9 | C5—N3—H3C | 110.2 |
O2—C4—H4B | 109.9 | Ni1—N3—H3C | 110.2 |
C3—C4—H4B | 109.9 | C5—N3—H3D | 110.2 |
H4A—C4—H4B | 108.3 | Ni1—N3—H3D | 110.2 |
N3—C5—C6 | 108.8 (2) | H3C—N3—H3D | 108.5 |
N3—C5—H5A | 109.9 | C7—N4—C6 | 117.5 (2) |
C6—C5—H5A | 109.9 | C7—N4—Ni1 | 108.31 (16) |
N3—C5—H5B | 109.9 | C6—N4—Ni1 | 107.04 (17) |
C6—C5—H5B | 109.9 | C7—N4—H4 | 110 (2) |
H5A—C5—H5B | 108.3 | C6—N4—H4 | 106 (2) |
N4—C6—C5 | 107.7 (2) | Ni1—N4—H4 | 107 (2) |
N4—C6—H6A | 110.2 | C8—O1—Ni1 | 110.90 (16) |
C5—C6—H6A | 110.2 | C8—O1—H1 | 111 (2) |
N4—C6—H6B | 110.2 | Ni1—O1—H1 | 128 (2) |
C5—C6—H6B | 110.2 | C4—O2—Ni1 | 110.29 (19) |
H6A—C6—H6B | 108.5 | C4—O2—H2 | 117 (3) |
N4—C7—C8 | 108.0 (2) | Ni1—O2—H2 | 120 (3) |
N4—C7—H7A | 110.1 | H8C—O8—H8D | 109 (3) |
C8—C7—H7A | 110.1 | N2—Ni1—N4 | 176.12 (9) |
N4—C7—H7B | 110.1 | N2—Ni1—N1 | 84.03 (9) |
C8—C7—H7B | 110.1 | N4—Ni1—N1 | 99.04 (9) |
H7A—C7—H7B | 108.4 | N2—Ni1—N3 | 98.52 (9) |
O1—C8—C7 | 107.7 (2) | N4—Ni1—N3 | 83.48 (9) |
O1—C8—H8A | 110.2 | N1—Ni1—N3 | 97.34 (9) |
C7—C8—H8A | 110.2 | N2—Ni1—O1 | 97.57 (8) |
O1—C8—H8B | 110.2 | N4—Ni1—O1 | 79.99 (8) |
C7—C8—H8B | 110.2 | N1—Ni1—O1 | 92.71 (8) |
H8A—C8—H8B | 108.5 | N3—Ni1—O1 | 161.81 (8) |
O3—C9—C12 | 134.2 (3) | N2—Ni1—O2 | 79.14 (9) |
O3—C9—C10 | 135.7 (3) | N4—Ni1—O2 | 97.54 (9) |
C12—C9—C10 | 90.0 (2) | N1—Ni1—O2 | 162.13 (9) |
O4—C10—C11 | 135.5 (2) | N3—Ni1—O2 | 91.11 (9) |
O4—C10—C9 | 135.3 (2) | O1—Ni1—O2 | 83.64 (8) |
| | | |
N1—C1—C2—N2 | −56.2 (3) | C2—N2—Ni1—N3 | −115.36 (18) |
N2—C3—C4—O2 | 51.7 (4) | C3—N2—Ni1—N3 | 118.4 (2) |
N3—C5—C6—N4 | −55.9 (3) | C2—N2—Ni1—O1 | 73.15 (18) |
N4—C7—C8—O1 | 54.0 (3) | C3—N2—Ni1—O1 | −53.1 (2) |
O3—C9—C10—O4 | 0.8 (6) | C2—N2—Ni1—O2 | 155.14 (18) |
C12—C9—C10—O4 | 179.7 (3) | C3—N2—Ni1—O2 | 28.9 (2) |
O3—C9—C10—C11 | −178.3 (4) | C7—N4—Ni1—N1 | 115.06 (19) |
C12—C9—C10—C11 | 0.6 (2) | C6—N4—Ni1—N1 | −117.35 (18) |
O4—C10—C11—O5 | −0.7 (6) | C7—N4—Ni1—N3 | −148.51 (19) |
C9—C10—C11—O5 | 178.3 (4) | C6—N4—Ni1—N3 | −20.92 (18) |
O4—C10—C11—C12 | −179.7 (3) | C7—N4—Ni1—O1 | 23.88 (18) |
C9—C10—C11—C12 | −0.6 (2) | C6—N4—Ni1—O1 | 151.47 (19) |
O5—C11—C12—O6 | 0.4 (7) | C7—N4—Ni1—O2 | −58.25 (19) |
C10—C11—C12—O6 | 179.4 (4) | C6—N4—Ni1—O2 | 69.34 (18) |
O5—C11—C12—C9 | −178.4 (4) | C1—N1—Ni1—N2 | −11.02 (17) |
C10—C11—C12—C9 | 0.6 (2) | C1—N1—Ni1—N4 | 171.36 (17) |
O3—C9—C12—O6 | −0.5 (7) | C1—N1—Ni1—N3 | 86.84 (17) |
C10—C9—C12—O6 | −179.4 (4) | C1—N1—Ni1—O1 | −108.35 (17) |
O3—C9—C12—C11 | 178.3 (4) | C1—N1—Ni1—O2 | −30.7 (4) |
C10—C9—C12—C11 | −0.6 (2) | C5—N3—Ni1—N2 | 174.72 (17) |
C2—C1—N1—Ni1 | 38.1 (3) | C5—N3—Ni1—N4 | −8.63 (18) |
C1—C2—N2—C3 | 166.4 (2) | C5—N3—Ni1—N1 | 89.69 (18) |
C1—C2—N2—Ni1 | 44.7 (3) | C5—N3—Ni1—O1 | −33.3 (4) |
C4—C3—N2—C2 | −173.5 (3) | C5—N3—Ni1—O2 | −106.09 (18) |
C4—C3—N2—Ni1 | −52.5 (3) | C8—O1—Ni1—N2 | −177.7 (2) |
C6—C5—N3—Ni1 | 36.1 (3) | C8—O1—Ni1—N4 | 5.33 (19) |
C8—C7—N4—C6 | −170.4 (2) | C8—O1—Ni1—N1 | −93.4 (2) |
C8—C7—N4—Ni1 | −49.0 (3) | C8—O1—Ni1—N3 | 30.3 (4) |
C5—C6—N4—C7 | 168.3 (2) | C8—O1—Ni1—O2 | 104.2 (2) |
C5—C6—N4—Ni1 | 46.3 (3) | C4—O2—Ni1—N2 | −1.1 (2) |
C7—C8—O1—Ni1 | −32.6 (3) | C4—O2—Ni1—N4 | 176.9 (2) |
C3—C4—O2—Ni1 | −26.4 (3) | C4—O2—Ni1—N1 | 18.9 (4) |
C2—N2—Ni1—N1 | −18.80 (17) | C4—O2—Ni1—N3 | −99.5 (2) |
C3—N2—Ni1—N1 | −145.1 (2) | C4—O2—Ni1—O1 | 97.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O3 | 0.90 | 2.24 | 3.007 (3) | 143 |
N1—H1D···O4i | 0.90 | 2.10 | 2.994 (3) | 170 |
N3—H3C···O7ii | 0.90 | 2.24 | 3.087 (6) | 157 |
N3—H3D···O4iii | 0.90 | 2.07 | 2.965 (3) | 170 |
O8—H8C···O6 | 0.84 (1) | 1.97 (5) | 2.659 (5) | 139 (7) |
O8—H8C···O7 | 0.84 (1) | 2.02 (6) | 2.488 (7) | 115 (5) |
O8—H8D···O5iv | 0.84 (1) | 2.08 (1) | 2.910 (5) | 174 (6) |
N4—H4···O3i | 0.82 (3) | 2.04 (3) | 2.820 (3) | 159 (3) |
O1—H1···O6 | 0.93 (4) | 1.71 (4) | 2.633 (3) | 172 (4) |
O2—H2···O8v | 0.87 (4) | 1.91 (4) | 2.735 (5) | 158 (4) |
O2—H2···O7ii | 0.87 (4) | 2.14 (4) | 2.711 (6) | 123 (3) |
N2—H3···O5iii | 0.85 (3) | 2.05 (3) | 2.842 (3) | 154 (3) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2. |