The structure of the title compound, μ-formato-bis{μ-N,N′-bis[1-(2-oxidophenyl)ethyl]-2-hydroxy-1,3-propanediamine}bis[(N,N-dimethylformamide)nickel(II)] N,N-dimethylformamide disolvate, [Ni3(CHO2)2(C19H24N2O3)2(C3H7NO)2]·2C3H7NO, comprises a centrosymmetric linear homotrinuclear nickel(II) complex. The central and terminal nickel(II) atoms have distorted octahedral coordination geometries.
Supporting information
CCDC reference: 272120
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.007 Å
- R factor = 0.050
- wR factor = 0.129
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.18 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.18 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for C10 - C11 .. 7.50 su
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N3
Alert level C
PLAT214_ALERT_2_C Atom C25 (Anion/Solvent) ADP max/min Ratio 4.10 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.59 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.32 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - C20 .. 5.34 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - C10 .. 5.30 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C9 .. 5.95 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C11 .. 5.34 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4
PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C6 1.43 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C14 -C19 1.45 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 28.80
From the CIF: _reflns_number_total 8345
From the CIF: _diffrn_reflns_limit_ max hkl 5. 14. 16.
From the CIF: _diffrn_reflns_limit_ min hkl -14. -13. -15.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 15. 16. 17.
Calculated minimum hkl -15. -16. -17.
0 ALERT level A = In general: serious problem
5 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
15 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.
Crystal data top
[Ni3(CO2H)2(C3H7NO)2(C19H24N2O3)2]·2C3H7NO | Z = 1 |
Mr = 1215.29 | F(000) = 642 |
Triclinic, P1 | Dx = 1.266 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5860 (12) Å | Cell parameters from 25 reflections |
b = 11.8200 (11) Å | θ = 2.9–28.8° |
c = 12.6520 (13) Å | µ = 0.94 mm−1 |
α = 96.500 (3)° | T = 299 K |
β = 107.030 (2)° | Needle, blue |
γ = 101.690 (4)° | 0.45 × 0.20 × 0.16 mm |
V = 1594.5 (3) Å3 | |
Data collection top
Oxford Diffraction Xcalibur CCD diffractometer | Rint = 0.036 |
Detector resolution: Sapphire CCD detector pixels mm-1 | θmax = 28.8° |
ω scans | h = −14→5 |
9225 measured reflections | k = −13→14 |
8345 independent reflections | l = −15→16 |
2904 reflections with I > 2σ(I) | |
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)] = 0.05 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3 |
6404 reflections | (Δ/σ)max < 0.001 |
349 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Special details top
Experimental. Elemental analysis was carried out with a Leco 932 C, H, N, S analyser and the
quantitative determination of nickel was by gravimetric analysis with
dimethylglioxyme. Calc. % for C49H71N7O13Ni3, C: 51.52, H: 6.27, N:
8.58, Ni: 15.41. Found % C: 51.09, H: 5.97, N: 8.34, Ni: 14.88. IR spectra
were recorded on a Mattson FTIR 1000 apparatus using a KBr disk. IR data
(cm-1): ν(N—H) 3285, ν(C—H)Ar 3053, ν(C—H)Aliph 2934–2797,
ν(C=O)DMF 1645 ν(C=C)Ar 1604, δCH2 1481, δ(C—H)Ar 737, ν(O—H)
2720 cm-1. Thermogravimetrical analysis was performed with a Shimadzu DTG 60
H instrument. The mass loss for DMF, calc. 19.19%, obs. 20.36%. |
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 | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.0389 (2) | |
Ni2 | 0.73193 (4) | 0.70623 (5) | 0.63957 (4) | 0.04632 (19) | |
N1 | 0.8329 (3) | 0.8695 (3) | 0.6064 (3) | 0.0577 (10) | |
N2 | 0.8483 (3) | 0.7380 (3) | 0.8068 (3) | 0.0623 (11) | |
N3 | 0.9190 (4) | 0.4280 (5) | 0.5774 (5) | 0.0971 (16) | |
N4 | 0.4007 (6) | 0.8640 (8) | 1.0342 (8) | 0.153 (3) | |
O1 | 0.6251 (2) | 0.6487 (2) | 0.47653 (19) | 0.0446 (7) | |
O2 | 0.6364 (2) | 0.5338 (2) | 0.65326 (19) | 0.0414 (7) | |
O3 | 0.5666 (2) | 0.3577 (3) | 0.4259 (2) | 0.0520 (8) | |
O4 | 0.3937 (3) | 0.2026 (3) | 0.3229 (2) | 0.0599 (8) | |
O5 | 0.8768 (2) | 0.6200 (3) | 0.6126 (2) | 0.0617 (9) | |
O6 | 1.0591 (3) | 0.9073 (4) | 0.7761 (3) | 0.1068 (14) | |
O7 | 0.2493 (4) | 0.9619 (5) | 0.9748 (4) | 0.1404 (19) | |
H1 | 0.9034 | 0.8518 | 0.5991 | 0.069* | |
H2A | 0.9166 | 0.7152 | 0.7999 | 0.075* | |
H6 | 1.1047 | 0.8930 | 0.8334 | 0.160* | |
C1 | 0.6678 (3) | 0.6757 (4) | 0.3925 (3) | 0.0439 (10) | |
C2 | 0.6333 (4) | 0.5844 (4) | 0.2939 (3) | 0.0552 (12) | |
H2 | 0.5834 | 0.5104 | 0.2891 | 0.066* | |
C3 | 0.6779 (4) | 0.6122 (5) | 0.2069 (4) | 0.0708 (15) | |
H3 | 0.6567 | 0.5561 | 0.1421 | 0.085* | |
C4 | 0.7575 (4) | 0.7278 (6) | 0.2157 (4) | 0.0773 (16) | |
H4 | 0.7883 | 0.7428 | 0.1572 | 0.093* | |
C5 | 0.7898 (4) | 0.8188 (5) | 0.3114 (4) | 0.0688 (14) | |
H5 | 0.8386 | 0.8928 | 0.3146 | 0.083* | |
C6 | 0.7462 (3) | 0.7938 (4) | 0.3996 (3) | 0.0511 (11) | |
C7 | 0.7748 (4) | 0.9055 (4) | 0.4953 (4) | 0.0635 (13) | |
H7 | 0.8386 | 0.9671 | 0.4844 | 0.076* | |
C8 | 0.6613 (5) | 0.9550 (5) | 0.4883 (4) | 0.0935 (19) | |
H8A | 0.6842 | 1.0231 | 0.5462 | 0.140* | |
H8B | 0.5965 | 0.8964 | 0.4981 | 0.140* | |
H8C | 0.6319 | 0.9765 | 0.4160 | 0.140* | |
C9 | 0.8820 (4) | 0.9797 (4) | 0.6961 (4) | 0.0795 (16) | |
H9A | 0.9292 | 1.0420 | 0.6706 | 0.095* | |
H9B | 0.8130 | 1.0057 | 0.7107 | 0.095* | |
C10 | 0.9639 (4) | 0.9533 (5) | 0.8017 (4) | 0.0718 (16) | |
H10 | 1.0047 | 1.0282 | 0.8541 | 0.086* | |
C11 | 0.9034 (5) | 0.8668 (5) | 0.8660 (4) | 0.0861 (18) | |
H11A | 0.9660 | 0.8686 | 0.9370 | 0.103* | |
H11B | 0.8376 | 0.8964 | 0.8833 | 0.103* | |
C12 | 0.8009 (4) | 0.6513 (5) | 0.8764 (4) | 0.0707 (15) | |
H12 | 0.8672 | 0.6673 | 0.9491 | 0.085* | |
C13 | 0.6880 (5) | 0.6782 (5) | 0.9019 (4) | 0.0929 (18) | |
H13A | 0.7054 | 0.7606 | 0.9315 | 0.139* | |
H13B | 0.6695 | 0.6335 | 0.9563 | 0.139* | |
H13C | 0.6177 | 0.6576 | 0.8341 | 0.139* | |
C14 | 0.7772 (3) | 0.5131 (4) | 0.8270 (3) | 0.0556 (12) | |
C15 | 0.8333 (4) | 0.4327 (6) | 0.8902 (4) | 0.0811 (17) | |
H15 | 0.8904 | 0.4650 | 0.9614 | 0.097* | |
C16 | 0.8097 (5) | 0.3053 (6) | 0.8542 (5) | 0.0942 (19) | |
H16 | 0.8537 | 0.2614 | 0.8999 | 0.113* | |
C17 | 0.7204 (5) | 0.2506 (5) | 0.7504 (4) | 0.0771 (15) | |
H17 | 0.6999 | 0.1697 | 0.7258 | 0.093* | |
C18 | 0.6622 (4) | 0.3272 (4) | 0.6839 (4) | 0.0563 (12) | |
H18 | 0.6026 | 0.2929 | 0.6144 | 0.068* | |
C19 | 0.6905 (3) | 0.4590 (4) | 0.7182 (3) | 0.0453 (11) | |
C20 | 0.8509 (4) | 0.5118 (5) | 0.5595 (4) | 0.0695 (15) | |
H20 | 0.7755 | 0.4874 | 0.5010 | 0.083* | |
C21 | 1.0300 (7) | 0.4615 (8) | 0.6719 (6) | 0.184 (4) | |
H21A | 1.0704 | 0.3981 | 0.6776 | 0.276* | |
H21B | 1.0095 | 0.4797 | 0.7390 | 0.276* | |
H21C | 1.0849 | 0.5295 | 0.6627 | 0.276* | |
C22 | 0.8761 (7) | 0.2995 (6) | 0.5112 (8) | 0.179 (4) | |
H22A | 0.9387 | 0.2584 | 0.5394 | 0.268* | |
H22B | 0.8636 | 0.3002 | 0.4328 | 0.268* | |
H22C | 0.7993 | 0.2607 | 0.5203 | 0.268* | |
C23 | 0.5073 (4) | 0.2529 (4) | 0.3618 (4) | 0.0589 (13) | |
H23 | 0.5591 | 0.2095 | 0.3425 | 0.071* | |
C24 | 0.3403 (7) | 0.9443 (8) | 1.0396 (7) | 0.142 (3) | |
H24 | 0.3738 | 0.9989 | 1.1065 | 0.170* | |
C25 | 0.5019 (8) | 0.8507 (14) | 1.1191 (11) | 0.376 (12) | |
H25A | 0.5303 | 0.7854 | 1.0931 | 0.564* | |
H25B | 0.4774 | 0.8366 | 1.1836 | 0.564* | |
H25C | 0.5680 | 0.9210 | 1.1394 | 0.564* | |
C26 | 0.3528 (15) | 0.7737 (10) | 0.9371 (13) | 0.319 (10) | |
H26A | 0.4068 | 0.7213 | 0.9425 | 0.478* | |
H26B | 0.3483 | 0.8080 | 0.8712 | 0.478* | |
H26C | 0.2710 | 0.7307 | 0.9320 | 0.478* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0316 (4) | 0.0519 (5) | 0.0298 (4) | 0.0085 (3) | 0.0060 (3) | 0.0079 (3) |
Ni2 | 0.0388 (3) | 0.0557 (4) | 0.0343 (3) | 0.0027 (3) | 0.0032 (2) | 0.0074 (3) |
N1 | 0.051 (2) | 0.061 (3) | 0.045 (2) | 0.0019 (19) | −0.0002 (17) | 0.0091 (19) |
N2 | 0.049 (2) | 0.075 (3) | 0.041 (2) | −0.010 (2) | −0.0008 (17) | 0.008 (2) |
N3 | 0.082 (3) | 0.127 (5) | 0.137 (5) | 0.063 (3) | 0.073 (3) | 0.072 (4) |
N4 | 0.110 (5) | 0.207 (9) | 0.209 (8) | 0.099 (5) | 0.078 (5) | 0.127 (7) |
O1 | 0.0341 (13) | 0.063 (2) | 0.0292 (14) | 0.0003 (13) | 0.0069 (11) | 0.0093 (13) |
O2 | 0.0324 (13) | 0.0528 (18) | 0.0308 (14) | 0.0052 (13) | 0.0000 (11) | 0.0127 (13) |
O3 | 0.0483 (16) | 0.068 (2) | 0.0412 (16) | 0.0195 (16) | 0.0142 (13) | 0.0087 (15) |
O4 | 0.0530 (18) | 0.067 (2) | 0.0505 (18) | 0.0109 (16) | 0.0099 (14) | 0.0002 (16) |
O5 | 0.0428 (16) | 0.082 (3) | 0.057 (2) | 0.0142 (17) | 0.0111 (14) | 0.0168 (18) |
O6 | 0.058 (2) | 0.141 (4) | 0.102 (3) | 0.007 (2) | 0.002 (2) | 0.038 (3) |
O7 | 0.087 (3) | 0.192 (5) | 0.116 (4) | 0.047 (3) | −0.018 (3) | 0.038 (3) |
C1 | 0.034 (2) | 0.058 (3) | 0.039 (2) | 0.013 (2) | 0.0067 (17) | 0.016 (2) |
C2 | 0.048 (2) | 0.074 (3) | 0.042 (3) | 0.012 (2) | 0.012 (2) | 0.016 (2) |
C3 | 0.067 (3) | 0.113 (5) | 0.041 (3) | 0.031 (3) | 0.023 (2) | 0.020 (3) |
C4 | 0.057 (3) | 0.130 (5) | 0.059 (3) | 0.025 (3) | 0.029 (3) | 0.042 (3) |
C5 | 0.048 (3) | 0.094 (4) | 0.064 (3) | 0.010 (3) | 0.014 (2) | 0.038 (3) |
C6 | 0.038 (2) | 0.068 (3) | 0.041 (2) | 0.006 (2) | 0.0055 (18) | 0.018 (2) |
C7 | 0.056 (3) | 0.063 (3) | 0.061 (3) | 0.005 (2) | 0.006 (2) | 0.025 (3) |
C8 | 0.100 (4) | 0.099 (5) | 0.071 (4) | 0.034 (4) | 0.006 (3) | 0.010 (3) |
C9 | 0.062 (3) | 0.076 (4) | 0.078 (4) | −0.005 (3) | 0.004 (3) | 0.017 (3) |
C10 | 0.034 (2) | 0.105 (4) | 0.054 (3) | −0.013 (3) | −0.004 (2) | 0.026 (3) |
C11 | 0.073 (3) | 0.111 (5) | 0.045 (3) | −0.008 (3) | 0.004 (3) | −0.005 (3) |
C12 | 0.062 (3) | 0.097 (4) | 0.036 (3) | −0.001 (3) | 0.002 (2) | 0.017 (3) |
C13 | 0.104 (4) | 0.109 (5) | 0.051 (3) | 0.004 (4) | 0.023 (3) | 0.003 (3) |
C14 | 0.039 (2) | 0.074 (4) | 0.046 (3) | 0.004 (2) | 0.0064 (19) | 0.022 (2) |
C15 | 0.052 (3) | 0.112 (5) | 0.065 (3) | 0.011 (3) | −0.004 (2) | 0.038 (3) |
C16 | 0.073 (3) | 0.130 (6) | 0.088 (4) | 0.043 (4) | 0.009 (3) | 0.062 (4) |
C17 | 0.082 (4) | 0.081 (4) | 0.082 (4) | 0.033 (3) | 0.031 (3) | 0.032 (3) |
C18 | 0.054 (3) | 0.069 (4) | 0.050 (3) | 0.021 (2) | 0.015 (2) | 0.020 (2) |
C19 | 0.0310 (19) | 0.070 (3) | 0.033 (2) | 0.009 (2) | 0.0078 (17) | 0.015 (2) |
C20 | 0.045 (3) | 0.095 (4) | 0.080 (4) | 0.018 (3) | 0.029 (3) | 0.035 (3) |
C21 | 0.133 (6) | 0.359 (13) | 0.143 (7) | 0.166 (8) | 0.065 (6) | 0.137 (8) |
C22 | 0.187 (8) | 0.098 (6) | 0.338 (13) | 0.065 (6) | 0.192 (9) | 0.046 (7) |
C23 | 0.064 (3) | 0.070 (4) | 0.050 (3) | 0.029 (3) | 0.023 (2) | 0.010 (3) |
C24 | 0.087 (5) | 0.202 (10) | 0.136 (7) | 0.028 (6) | 0.023 (5) | 0.080 (7) |
C25 | 0.146 (8) | 0.79 (3) | 0.393 (18) | 0.255 (14) | 0.153 (10) | 0.48 (2) |
C26 | 0.42 (2) | 0.200 (14) | 0.39 (2) | 0.013 (14) | 0.287 (19) | −0.010 (13) |
Geometric parameters (Å, º) top
Ni1—Ni2 | 3.1421 (6) | C12—C13 | 1.521 (7) |
Ni1—O1 | 2.148 (3) | C12—N2 | 1.545 (5) |
Ni1—O1i | 2.148 (3) | C12—C14 | 1.618 (6) |
Ni1—O2i | 2.047 (2) | C12—H12 | 0.9800 |
Ni1—O2 | 2.047 (2) | C13—H13A | 0.9600 |
Ni1—O3 | 2.213 (3) | C13—H13B | 0.9600 |
Ni1—O3i | 2.213 (3) | C13—H13C | 0.9600 |
Ni2—O1 | 2.024 (2) | C14—C19 | 1.429 (5) |
Ni2—O2 | 2.165 (3) | C14—C15 | 1.444 (6) |
Ni2—O4i | 2.105 (3) | C15—C16 | 1.468 (7) |
Ni2—O5 | 2.218 (3) | C15—H15 | 0.9300 |
Ni2—N1 | 2.196 (3) | C16—C17 | 1.398 (6) |
Ni2—N2 | 2.093 (3) | C16—H16 | 0.9300 |
O6—H6 | 0.8200 | C17—C18 | 1.439 (6) |
N1—H1 | 0.9100 | C17—H17 | 0.9300 |
N2—H2A | 0.9100 | C18—C19 | 1.510 (6) |
C1—O1 | 1.341 (4) | C18—H18 | 0.9300 |
C1—C2 | 1.453 (5) | C19—O2 | 1.392 (4) |
C1—C6 | 1.480 (6) | C20—O5 | 1.308 (6) |
C2—C3 | 1.390 (6) | C20—N3 | 1.385 (6) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.458 (7) | C21—N3 | 1.423 (8) |
C3—H3 | 0.9300 | C21—H21A | 0.9600 |
C4—C5 | 1.428 (7) | C21—H21B | 0.9600 |
C4—H4 | 0.9300 | C21—H21C | 0.9600 |
C5—C6 | 1.390 (6) | C22—N3 | 1.555 (8) |
C5—H5 | 0.9300 | C22—H22A | 0.9600 |
C6—C7 | 1.595 (6) | C22—H22B | 0.9600 |
C7—N1 | 1.519 (5) | C22—H22C | 0.9600 |
C7—C8 | 1.527 (6) | C23—O4 | 1.251 (5) |
C7—H7 | 0.9800 | C23—O3 | 1.329 (5) |
C8—H8A | 0.9600 | C23—H23 | 0.9300 |
C8—H8B | 0.9600 | C24—O7 | 1.204 (7) |
C8—H8C | 0.9600 | C24—N4 | 1.294 (9) |
C9—C10 | 1.501 (6) | C24—H24 | 0.9300 |
C9—N1 | 1.516 (5) | C25—N4 | 1.390 (10) |
C9—H9A | 0.9700 | C25—H25A | 0.9600 |
C9—H9B | 0.9700 | C25—H25B | 0.9600 |
C10—O6 | 1.426 (6) | C25—H25C | 0.9600 |
C10—C11 | 1.559 (6) | C26—N4 | 1.421 (12) |
C10—H10 | 0.9800 | C26—H26A | 0.9600 |
C11—N2 | 1.533 (6) | C26—H26B | 0.9600 |
C11—H11A | 0.9700 | C26—H26C | 0.9600 |
C11—H11B | 0.9700 | | |
| | | |
Ni2—O1—Ni1 | 97.68 (10) | N2—C11—H11B | 108.0 |
Ni1—O2—Ni2 | 96.43 (10) | C10—C11—H11B | 108.0 |
O1—Ni1—O1i | 180.0 | H11A—C11—H11B | 107.2 |
O1—Ni1—O3 | 99.04 (10) | C13—C12—N2 | 110.8 (4) |
O1i—Ni1—O3 | 80.96 (10) | C13—C12—C14 | 111.7 (4) |
O1—Ni1—O3i | 80.96 (10) | N2—C12—C14 | 116.0 (4) |
O1i—Ni1—O3i | 99.04 (10) | C13—C12—H12 | 105.8 |
O2i—Ni1—O2 | 180.0 | N2—C12—H12 | 105.8 |
O2i—Ni1—O1 | 98.87 (9) | C14—C12—H12 | 105.8 |
O2—Ni1—O1 | 81.13 (9) | C12—C13—H13A | 109.5 |
O2i—Ni1—O1i | 81.13 (9) | C12—C13—H13B | 109.5 |
O2—Ni1—O1i | 98.87 (9) | H13A—C13—H13B | 109.5 |
O2i—Ni1—O3 | 85.13 (10) | C12—C13—H13C | 109.5 |
O2—Ni1—O3 | 94.87 (10) | H13A—C13—H13C | 109.5 |
O2i—Ni1—O3i | 94.87 (10) | H13B—C13—H13C | 109.5 |
O2—Ni1—O3i | 85.13 (10) | C19—C14—C15 | 114.2 (4) |
O3—Ni1—O3i | 180.00 (13) | C19—C14—C12 | 121.8 (4) |
O1—Ni2—N2 | 170.49 (13) | C15—C14—C12 | 123.8 (4) |
O1—Ni2—O4i | 93.50 (10) | C14—C15—C16 | 127.0 (4) |
N2—Ni2—O4i | 93.90 (13) | C14—C15—H15 | 116.5 |
O1—Ni2—O2 | 81.25 (10) | C16—C15—H15 | 116.5 |
N2—Ni2—O2 | 91.93 (12) | C17—C16—C15 | 119.2 (5) |
O4i—Ni2—O2 | 96.91 (11) | C17—C16—H16 | 120.4 |
O1—Ni2—N1 | 93.56 (11) | C15—C16—H16 | 120.4 |
N2—Ni2—N1 | 92.56 (13) | C16—C17—C18 | 115.9 (5) |
O4i—Ni2—N1 | 88.80 (13) | C16—C17—H17 | 122.1 |
O2—Ni2—N1 | 172.48 (11) | C18—C17—H17 | 122.1 |
O1—Ni2—O5 | 91.01 (10) | C17—C18—C19 | 125.0 (4) |
N2—Ni2—O5 | 81.80 (13) | C17—C18—H18 | 117.5 |
O4i—Ni2—O5 | 175.14 (11) | C19—C18—H18 | 117.5 |
O2—Ni2—O5 | 85.55 (11) | O2—C19—C14 | 116.2 (4) |
N1—Ni2—O5 | 89.13 (13) | O2—C19—C18 | 125.3 (3) |
C1—O1—Ni2 | 121.5 (2) | C14—C19—C18 | 118.5 (4) |
C1—O1—Ni1 | 135.1 (2) | O5—C20—N3 | 129.7 (5) |
C19—O2—Ni1 | 131.4 (2) | O5—C20—H20 | 115.2 |
C19—O2—Ni2 | 125.6 (2) | N3—C20—H20 | 115.2 |
C23—O3—Ni1 | 132.4 (3) | N3—C21—H21A | 109.5 |
C23—O4—Ni2i | 117.5 (3) | N3—C21—H21B | 109.5 |
C20—O5—Ni2 | 122.9 (3) | H21A—C21—H21B | 109.5 |
C10—O6—H6 | 109.5 | N3—C21—H21C | 109.5 |
O1—C1—C2 | 117.2 (4) | H21A—C21—H21C | 109.5 |
O1—C1—C6 | 121.5 (4) | H21B—C21—H21C | 109.5 |
C2—C1—C6 | 121.4 (4) | N3—C22—H22A | 109.5 |
C3—C2—C1 | 117.2 (4) | N3—C22—H22B | 109.5 |
C3—C2—H2 | 121.4 | H22A—C22—H22B | 109.5 |
C1—C2—H2 | 121.4 | N3—C22—H22C | 109.5 |
C2—C3—C4 | 121.0 (5) | H22A—C22—H22C | 109.5 |
C2—C3—H3 | 119.5 | H22B—C22—H22C | 109.5 |
C4—C3—H3 | 119.5 | O4—C23—O3 | 131.1 (4) |
C5—C4—C3 | 122.0 (4) | O4—C23—H23 | 114.5 |
C5—C4—H4 | 119.0 | O3—C23—H23 | 114.5 |
C3—C4—H4 | 119.0 | O7—C24—N4 | 132.4 (10) |
C6—C5—C4 | 118.3 (5) | O7—C24—H24 | 113.8 |
C6—C5—H5 | 120.9 | N4—C24—H24 | 113.8 |
C4—C5—H5 | 120.9 | N4—C25—H25A | 109.5 |
C5—C6—C1 | 120.0 (4) | N4—C25—H25B | 109.5 |
C5—C6—C7 | 113.8 (4) | H25A—C25—H25B | 109.5 |
C1—C6—C7 | 125.7 (4) | N4—C25—H25C | 109.5 |
N1—C7—C8 | 115.3 (4) | H25A—C25—H25C | 109.5 |
N1—C7—C6 | 106.4 (3) | H25B—C25—H25C | 109.5 |
C8—C7—C6 | 112.9 (3) | N4—C26—H26A | 109.5 |
N1—C7—H7 | 107.3 | N4—C26—H26B | 109.5 |
C8—C7—H7 | 107.3 | H26A—C26—H26B | 109.5 |
C6—C7—H7 | 107.3 | N4—C26—H26C | 109.5 |
C7—C8—H8A | 109.5 | H26A—C26—H26C | 109.5 |
C7—C8—H8B | 109.5 | H26B—C26—H26C | 109.5 |
H8A—C8—H8B | 109.5 | C9—N1—C7 | 107.3 (3) |
C7—C8—H8C | 109.5 | C9—N1—Ni2 | 120.0 (3) |
H8A—C8—H8C | 109.5 | C7—N1—Ni2 | 117.0 (2) |
H8B—C8—H8C | 109.5 | C9—N1—H1 | 103.4 |
C10—C9—N1 | 109.0 (4) | C7—N1—H1 | 103.4 |
C10—C9—H9A | 109.9 | Ni2—N1—H1 | 103.4 |
N1—C9—H9A | 109.9 | C11—N2—C12 | 116.5 (3) |
C10—C9—H9B | 109.9 | C11—N2—Ni2 | 117.2 (3) |
N1—C9—H9B | 109.9 | C12—N2—Ni2 | 112.9 (2) |
H9A—C9—H9B | 108.3 | C11—N2—H2A | 102.4 |
O6—C10—C9 | 108.7 (4) | C12—N2—H2A | 102.4 |
O6—C10—C11 | 106.9 (4) | Ni2—N2—H2A | 102.4 |
C9—C10—C11 | 118.7 (4) | C20—N3—C21 | 115.5 (6) |
O6—C10—H10 | 107.3 | C20—N3—C22 | 125.0 (6) |
C9—C10—H10 | 107.3 | C21—N3—C22 | 119.1 (6) |
C11—C10—H10 | 107.3 | C24—N4—C25 | 126.1 (12) |
N2—C11—C10 | 117.3 (4) | C24—N4—C26 | 117.7 (10) |
N2—C11—H11A | 108.0 | C25—N4—C26 | 115.9 (10) |
C10—C11—H11A | 108.0 | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O7ii | 0.82 | 2.01 | 2.721 (6) | 145 |
N1—H1···O6 | 0.91 | 2.35 | 2.773 (5) | 108 |
N2—H2···O5 | 0.91 | 2.37 | 2.825 (5) | 110 |
Symmetry code: (ii) x, y, z+1. |