In the new nickel(II) complex [14,25-dichloro-2,11-diphenyltetracyclo[20.4.0.04,9.012,17]hexacosa-2,10,12,14,16,22,24,26-octaene-19,20-dionato(2-)]nickel(II) dichloromethane sesquisolvate, [Ni(C34H26Cl2N4O2)]·1.5CH2Cl2, the nickel(II) ion is four-coordinate and displays approximately square-planar coordination geometry. It binds to two deprotonated oxamide N atoms and two imine N atoms of the macrocyclic ligand. The C atom of one of the two dichloromethane solvent molecules lies on a twofold axis.
Supporting information
CCDC reference: 259898
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C22 - C29 .. 11.43 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C23 - C28 .. 7.68 su
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C24 - C25 .. 6.72 su
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C35
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.53 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A .. CL1 .. 2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20A .. CL1 .. 2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H26 .. O1 .. 2.61 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
N3 -NI1 -N1 -C1 -48.20 1.20 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4
N3 -NI1 -N1 -C34 128.30 1.10 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9
N4 -NI1 -N2 -C2 -131.80 1.20 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12
N4 -NI1 -N2 -C3 51.80 1.40 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14
N1 -NI1 -N3 -C9 90.30 1.20 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17
N1 -NI1 -N3 -C16 -83.70 1.20 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 -C22 83.20 1.30 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 -C21 -81.70 1.30 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
21 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
13 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
[14,25-dichloro-2,11-diphenyl-tetracyclo[20.4.0.0
4,9.0
12,17]hexacosa-
2,10,12,14,16,22,24,26-octaene-19,20-dionato(2-)]nickel(II) dichloromethane
sesquisolvate
top
Crystal data top
[Ni(C34H26Cl2N4O2)]·1.5CH2Cl2 | F(000) = 3192 |
Mr = 779.59 | Dx = 1.542 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 26.745 (7) Å | Cell parameters from 985 reflections |
b = 12.520 (3) Å | θ = 3.2–25.4° |
c = 22.820 (6) Å | µ = 1.02 mm−1 |
β = 118.454 (4)° | T = 293 K |
V = 6718 (3) Å3 | Block, red |
Z = 8 | 0.22 × 0.20 × 0.18 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5930 independent reflections |
Radiation source: fine-focus sealed tube | 4119 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −31→31 |
Tmin = 0.754, Tmax = 0.833 | k = −10→14 |
17189 measured reflections | l = −24→27 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0273P)2 + 0.4655P] where P = (Fo2 + 2Fc2)/3 |
5930 reflections | (Δ/σ)max < 0.001 |
429 parameters | Δρmax = 0.80 e Å−3 |
9 restraints | Δρmin = −0.78 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) |
Ni1 | 0.136067 (19) | 0.24467 (3) | 0.28015 (2) | 0.02877 (14) | |
Cl1 | 0.21169 (5) | 0.44373 (9) | 0.60820 (5) | 0.0550 (3) | |
Cl2 | −0.08844 (4) | 0.05545 (9) | −0.03365 (5) | 0.0547 (3) | |
O1 | 0.16488 (12) | 0.0200 (2) | 0.40832 (13) | 0.0477 (7) | |
O2 | 0.10162 (14) | −0.0542 (2) | 0.28016 (15) | 0.0605 (8) | |
N1 | 0.15136 (12) | 0.1917 (2) | 0.36341 (14) | 0.0303 (7) | |
N2 | 0.09390 (13) | 0.1211 (2) | 0.24467 (15) | 0.0341 (7) | |
N3 | 0.12618 (12) | 0.2863 (2) | 0.19714 (14) | 0.0306 (7) | |
N4 | 0.17227 (12) | 0.3772 (2) | 0.31286 (13) | 0.0308 (7) | |
C1 | 0.14673 (16) | 0.0826 (3) | 0.36179 (19) | 0.0349 (8) | |
C2 | 0.11172 (16) | 0.0407 (3) | 0.29040 (19) | 0.0373 (9) | |
C3 | 0.05147 (15) | 0.1057 (3) | 0.17928 (18) | 0.0339 (8) | |
C4 | 0.00876 (17) | 0.0280 (3) | 0.1632 (2) | 0.0441 (10) | |
H4 | 0.0097 | −0.0151 | 0.1969 | 0.053* | |
C5 | −0.03418 (17) | 0.0142 (3) | 0.0991 (2) | 0.0457 (10) | |
H5 | −0.0620 | −0.0374 | 0.0898 | 0.055* | |
C6 | −0.03576 (15) | 0.0770 (3) | 0.04887 (19) | 0.0399 (9) | |
C7 | 0.00338 (16) | 0.1559 (3) | 0.06214 (18) | 0.0386 (9) | |
H7 | 0.0007 | 0.1994 | 0.0277 | 0.046* | |
C8 | 0.04760 (15) | 0.1719 (3) | 0.12703 (18) | 0.0330 (8) | |
C9 | 0.08988 (15) | 0.2555 (3) | 0.13780 (17) | 0.0317 (8) | |
C10 | 0.08851 (16) | 0.3049 (3) | 0.07741 (17) | 0.0378 (9) | |
C11 | 0.10593 (18) | 0.2469 (4) | 0.0383 (2) | 0.0528 (11) | |
H11 | 0.1186 | 0.1769 | 0.0495 | 0.063* | |
C12 | 0.1042 (2) | 0.2945 (5) | −0.0178 (2) | 0.0676 (14) | |
H12 | 0.1156 | 0.2561 | −0.0443 | 0.081* | |
C13 | 0.0858 (2) | 0.3976 (5) | −0.0340 (2) | 0.0707 (16) | |
H13 | 0.0848 | 0.4290 | −0.0714 | 0.085* | |
C14 | 0.0687 (2) | 0.4548 (4) | 0.0045 (2) | 0.0664 (14) | |
H14 | 0.0563 | 0.5249 | −0.0068 | 0.080* | |
C15 | 0.06988 (17) | 0.4084 (3) | 0.0599 (2) | 0.0491 (11) | |
H15 | 0.0580 | 0.4473 | 0.0857 | 0.059* | |
C16 | 0.17342 (14) | 0.3592 (3) | 0.20815 (17) | 0.0309 (8) | |
H16 | 0.1648 | 0.3956 | 0.1664 | 0.037* | |
C17 | 0.22718 (17) | 0.2923 (3) | 0.2310 (2) | 0.0465 (10) | |
H17A | 0.2325 | 0.2485 | 0.2686 | 0.056* | |
H17B | 0.2229 | 0.2452 | 0.1952 | 0.056* | |
C18 | 0.27923 (18) | 0.3628 (4) | 0.2513 (2) | 0.0633 (13) | |
H18A | 0.2764 | 0.3992 | 0.2123 | 0.076* | |
H18B | 0.3132 | 0.3188 | 0.2696 | 0.076* | |
C19 | 0.2839 (2) | 0.4449 (4) | 0.3029 (2) | 0.0727 (16) | |
H19A | 0.2916 | 0.4087 | 0.3440 | 0.087* | |
H19B | 0.3153 | 0.4929 | 0.3124 | 0.087* | |
C20 | 0.2297 (2) | 0.5083 (3) | 0.2780 (2) | 0.0531 (12) | |
H20A | 0.2242 | 0.5491 | 0.2393 | 0.064* | |
H20B | 0.2337 | 0.5587 | 0.3123 | 0.064* | |
C21 | 0.17726 (16) | 0.4407 (3) | 0.25950 (16) | 0.0334 (8) | |
H21 | 0.1439 | 0.4874 | 0.2381 | 0.040* | |
C22 | 0.18044 (14) | 0.4219 (3) | 0.36823 (16) | 0.0291 (8) | |
C23 | 0.18909 (16) | 0.5400 (3) | 0.37790 (17) | 0.0320 (8) | |
C24 | 0.24087 (18) | 0.5857 (3) | 0.42269 (19) | 0.0437 (10) | |
H24 | 0.2721 | 0.5427 | 0.4486 | 0.052* | |
C25 | 0.2454 (2) | 0.6966 (4) | 0.4282 (2) | 0.0570 (13) | |
H25 | 0.2799 | 0.7279 | 0.4575 | 0.068* | |
C26 | 0.1986 (2) | 0.7602 (3) | 0.3904 (2) | 0.0597 (13) | |
H26 | 0.2020 | 0.8341 | 0.3944 | 0.072* | |
C27 | 0.1479 (2) | 0.7155 (3) | 0.3474 (2) | 0.0552 (12) | |
H27 | 0.1166 | 0.7589 | 0.3224 | 0.066* | |
C28 | 0.14273 (17) | 0.6056 (3) | 0.34081 (19) | 0.0401 (9) | |
H28 | 0.1079 | 0.5754 | 0.3113 | 0.048* | |
C29 | 0.17913 (14) | 0.3614 (3) | 0.42301 (16) | 0.0293 (8) | |
C30 | 0.19155 (15) | 0.4193 (3) | 0.48156 (17) | 0.0337 (8) | |
H30 | 0.1979 | 0.4925 | 0.4828 | 0.040* | |
C31 | 0.19439 (16) | 0.3698 (3) | 0.53612 (17) | 0.0370 (9) | |
C32 | 0.18430 (18) | 0.2624 (3) | 0.53578 (19) | 0.0463 (10) | |
H32 | 0.1858 | 0.2295 | 0.5731 | 0.056* | |
C33 | 0.17185 (17) | 0.2038 (3) | 0.47932 (19) | 0.0421 (9) | |
H33 | 0.1655 | 0.1308 | 0.4795 | 0.051* | |
C34 | 0.16838 (14) | 0.2506 (3) | 0.42134 (17) | 0.0309 (8) | |
Cl3 | 0.09208 (8) | 0.67923 (13) | 0.13103 (10) | 0.1111 (6) | |
Cl4 | 0.01510 (8) | 0.71881 (19) | 0.18506 (8) | 0.1294 (8) | |
C35 | 0.0547 (3) | 0.7702 (4) | 0.1514 (3) | 0.0890 (18) | |
H35A | 0.0815 | 0.8209 | 0.1828 | 0.107* | |
H35B | 0.0296 | 0.8095 | 0.1114 | 0.107* | |
Cl5 | 0.99241 (14) | 0.4072 (3) | 0.18441 (16) | 0.2028 (14) | |
C36 | 1.0000 | 0.3322 (6) | 0.2500 | 0.150 (6) | |
H36A | 1.0331 | 0.2866 | 0.2641 | 0.180* | 0.50 |
H36B | 0.9669 | 0.2866 | 0.2359 | 0.180* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0386 (3) | 0.0235 (2) | 0.0259 (2) | −0.0022 (2) | 0.0168 (2) | 0.00044 (19) |
Cl1 | 0.0744 (8) | 0.0645 (7) | 0.0340 (5) | 0.0013 (6) | 0.0321 (5) | −0.0078 (5) |
Cl2 | 0.0441 (6) | 0.0606 (7) | 0.0444 (6) | −0.0059 (5) | 0.0089 (5) | −0.0157 (5) |
O1 | 0.0667 (19) | 0.0280 (14) | 0.0427 (16) | 0.0035 (13) | 0.0214 (15) | 0.0100 (12) |
O2 | 0.081 (2) | 0.0253 (15) | 0.0553 (19) | −0.0050 (14) | 0.0159 (16) | −0.0004 (13) |
N1 | 0.0379 (17) | 0.0235 (16) | 0.0288 (16) | −0.0003 (13) | 0.0154 (14) | 0.0035 (12) |
N2 | 0.0421 (18) | 0.0254 (16) | 0.0346 (17) | −0.0043 (13) | 0.0180 (15) | −0.0007 (13) |
N3 | 0.0383 (17) | 0.0279 (15) | 0.0289 (16) | −0.0020 (13) | 0.0188 (14) | −0.0020 (12) |
N4 | 0.0439 (18) | 0.0261 (16) | 0.0242 (15) | −0.0008 (13) | 0.0176 (14) | 0.0031 (12) |
C1 | 0.041 (2) | 0.027 (2) | 0.041 (2) | 0.0013 (16) | 0.0226 (18) | 0.0053 (17) |
C2 | 0.040 (2) | 0.028 (2) | 0.041 (2) | −0.0005 (16) | 0.0177 (18) | 0.0017 (17) |
C3 | 0.037 (2) | 0.0308 (19) | 0.035 (2) | −0.0034 (16) | 0.0187 (17) | −0.0066 (16) |
C4 | 0.049 (2) | 0.038 (2) | 0.046 (2) | −0.0072 (18) | 0.023 (2) | −0.0015 (18) |
C5 | 0.038 (2) | 0.042 (2) | 0.056 (3) | −0.0124 (18) | 0.021 (2) | −0.010 (2) |
C6 | 0.032 (2) | 0.042 (2) | 0.039 (2) | 0.0004 (17) | 0.0113 (17) | −0.0097 (18) |
C7 | 0.042 (2) | 0.041 (2) | 0.033 (2) | 0.0004 (18) | 0.0176 (18) | −0.0039 (17) |
C8 | 0.034 (2) | 0.031 (2) | 0.034 (2) | 0.0009 (15) | 0.0162 (17) | −0.0051 (16) |
C9 | 0.039 (2) | 0.0296 (19) | 0.0274 (18) | −0.0010 (16) | 0.0169 (16) | −0.0036 (16) |
C10 | 0.039 (2) | 0.046 (2) | 0.0238 (19) | −0.0121 (18) | 0.0107 (17) | −0.0029 (17) |
C11 | 0.062 (3) | 0.064 (3) | 0.037 (2) | −0.009 (2) | 0.028 (2) | −0.008 (2) |
C12 | 0.060 (3) | 0.113 (5) | 0.038 (3) | −0.016 (3) | 0.030 (2) | −0.015 (3) |
C13 | 0.056 (3) | 0.115 (5) | 0.032 (3) | −0.028 (3) | 0.013 (2) | 0.015 (3) |
C14 | 0.058 (3) | 0.077 (4) | 0.045 (3) | −0.005 (3) | 0.010 (2) | 0.022 (3) |
C15 | 0.051 (3) | 0.050 (3) | 0.038 (2) | −0.003 (2) | 0.015 (2) | 0.0065 (19) |
C16 | 0.036 (2) | 0.0316 (19) | 0.0249 (18) | −0.0041 (15) | 0.0145 (16) | 0.0014 (15) |
C17 | 0.050 (3) | 0.043 (2) | 0.053 (3) | 0.0076 (19) | 0.030 (2) | 0.007 (2) |
C18 | 0.039 (3) | 0.079 (3) | 0.068 (3) | 0.007 (2) | 0.023 (2) | 0.030 (3) |
C19 | 0.057 (3) | 0.103 (4) | 0.040 (3) | −0.041 (3) | 0.008 (2) | 0.012 (3) |
C20 | 0.084 (4) | 0.051 (3) | 0.032 (2) | −0.031 (2) | 0.034 (2) | −0.0076 (19) |
C21 | 0.049 (2) | 0.0264 (18) | 0.0258 (18) | −0.0030 (16) | 0.0187 (17) | 0.0050 (15) |
C22 | 0.032 (2) | 0.0272 (19) | 0.0274 (19) | 0.0022 (14) | 0.0137 (16) | 0.0039 (15) |
C23 | 0.048 (2) | 0.0260 (19) | 0.0257 (18) | −0.0026 (16) | 0.0209 (17) | −0.0026 (14) |
C24 | 0.056 (3) | 0.044 (2) | 0.032 (2) | −0.0042 (19) | 0.0210 (19) | −0.0044 (17) |
C25 | 0.082 (3) | 0.052 (3) | 0.048 (3) | −0.035 (3) | 0.040 (3) | −0.027 (2) |
C26 | 0.111 (4) | 0.031 (2) | 0.058 (3) | −0.009 (3) | 0.056 (3) | −0.006 (2) |
C27 | 0.093 (4) | 0.033 (2) | 0.050 (3) | 0.014 (2) | 0.042 (3) | 0.008 (2) |
C28 | 0.052 (2) | 0.030 (2) | 0.039 (2) | 0.0004 (17) | 0.023 (2) | 0.0017 (17) |
C29 | 0.035 (2) | 0.0287 (19) | 0.0271 (18) | 0.0048 (15) | 0.0171 (16) | 0.0012 (15) |
C30 | 0.040 (2) | 0.032 (2) | 0.033 (2) | 0.0020 (16) | 0.0210 (17) | −0.0011 (16) |
C31 | 0.043 (2) | 0.046 (2) | 0.0272 (19) | 0.0032 (17) | 0.0206 (17) | −0.0036 (17) |
C32 | 0.065 (3) | 0.050 (3) | 0.031 (2) | 0.003 (2) | 0.028 (2) | 0.0077 (19) |
C33 | 0.061 (3) | 0.032 (2) | 0.039 (2) | −0.0029 (19) | 0.028 (2) | 0.0058 (17) |
C34 | 0.0347 (19) | 0.0320 (19) | 0.0273 (18) | 0.0025 (16) | 0.0158 (15) | 0.0022 (16) |
Cl3 | 0.1355 (15) | 0.0722 (10) | 0.1295 (15) | 0.0089 (10) | 0.0662 (13) | −0.0233 (10) |
Cl4 | 0.0990 (13) | 0.210 (2) | 0.0677 (10) | −0.0641 (14) | 0.0302 (9) | −0.0138 (12) |
C35 | 0.103 (5) | 0.077 (4) | 0.100 (5) | 0.000 (3) | 0.059 (4) | −0.004 (3) |
Cl5 | 0.217 (3) | 0.236 (3) | 0.194 (3) | 0.100 (3) | 0.130 (2) | 0.046 (2) |
C36 | 0.100 (7) | 0.048 (5) | 0.35 (2) | 0.000 | 0.147 (11) | 0.000 |
C22 | 0.0335 (17) | 0.0266 (17) | 0.0257 (17) | 0.0013 (13) | −0.0018 (13) | −0.0134 (14) |
C23 | 0.0295 (16) | 0.0204 (15) | 0.0199 (15) | 0.0013 (12) | 0.0008 (12) | −0.0090 (13) |
C24 | 0.0234 (15) | 0.0239 (16) | 0.0242 (16) | −0.0015 (12) | −0.0038 (12) | −0.0074 (14) |
O20 | 0.0344 (14) | 0.0505 (17) | 0.0646 (18) | −0.0028 (12) | 0.0126 (12) | −0.0052 (14) |
Geometric parameters (Å, º) top
Ni1—N3 | 1.858 (3) | C17—H17A | 0.9700 |
Ni1—N2 | 1.858 (3) | C17—H17B | 0.9700 |
Ni1—N1 | 1.865 (3) | C18—C19 | 1.524 (7) |
Ni1—N4 | 1.887 (3) | C18—H18A | 0.9700 |
Cl1—C31 | 1.747 (4) | C18—H18B | 0.9700 |
Cl2—C6 | 1.754 (4) | C19—C20 | 1.507 (7) |
O1—C1 | 1.219 (4) | C19—H19A | 0.9700 |
O2—C2 | 1.217 (4) | C19—H19B | 0.9700 |
N1—C1 | 1.370 (4) | C20—C21 | 1.516 (5) |
N1—C34 | 1.387 (4) | C20—H20A | 0.9700 |
N2—C2 | 1.361 (4) | C20—H20B | 0.9700 |
N2—C3 | 1.392 (4) | C21—H21 | 0.9800 |
N3—C9 | 1.293 (4) | C22—C29 | 1.476 (4) |
N3—C16 | 1.480 (4) | C22—C23 | 1.497 (5) |
N4—C22 | 1.301 (4) | C23—C28 | 1.389 (5) |
N4—C21 | 1.512 (4) | C23—C24 | 1.393 (5) |
C1—C2 | 1.534 (5) | C24—C25 | 1.394 (6) |
C3—C4 | 1.410 (5) | C24—H24 | 0.9300 |
C3—C8 | 1.414 (5) | C25—C26 | 1.383 (7) |
C4—C5 | 1.374 (5) | C25—H25 | 0.9300 |
C4—H4 | 0.9300 | C26—C27 | 1.360 (7) |
C5—C6 | 1.375 (5) | C26—H26 | 0.9300 |
C5—H5 | 0.9300 | C27—C28 | 1.384 (5) |
C6—C7 | 1.364 (5) | C27—H27 | 0.9300 |
C7—C8 | 1.401 (5) | C28—H28 | 0.9300 |
C7—H7 | 0.9300 | C29—C34 | 1.414 (5) |
C8—C9 | 1.474 (5) | C29—C30 | 1.413 (5) |
C9—C10 | 1.495 (5) | C30—C31 | 1.360 (5) |
C10—C15 | 1.378 (5) | C30—H30 | 0.9300 |
C10—C11 | 1.392 (5) | C31—C32 | 1.371 (5) |
C11—C12 | 1.392 (6) | C32—C33 | 1.378 (5) |
C11—H11 | 0.9300 | C32—H32 | 0.9300 |
C12—C13 | 1.368 (7) | C33—C34 | 1.409 (5) |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—C14 | 1.368 (7) | Cl3—C35 | 1.718 (5) |
C13—H13 | 0.9300 | Cl4—C35 | 1.704 (5) |
C14—C15 | 1.378 (6) | C35—H35A | 0.9700 |
C14—H14 | 0.9300 | C35—H35B | 0.9700 |
C15—H15 | 0.9300 | Cl5—C36 | 1.695 (4) |
C16—C21 | 1.520 (5) | C36—Cl5i | 1.695 (4) |
C16—C17 | 1.525 (5) | C36—H36A | 0.9700 |
C16—H16 | 0.9800 | C36—H36B | 0.9700 |
C17—C18 | 1.522 (6) | | |
| | | |
N3—Ni1—N2 | 91.55 (12) | C17—C18—C19 | 110.6 (4) |
N3—Ni1—N1 | 173.81 (12) | C17—C18—H18A | 109.5 |
N2—Ni1—N1 | 86.60 (12) | C19—C18—H18A | 109.5 |
N3—Ni1—N4 | 87.35 (12) | C17—C18—H18B | 109.5 |
N2—Ni1—N4 | 174.56 (13) | C19—C18—H18B | 109.5 |
N1—Ni1—N4 | 95.03 (12) | H18A—C18—H18B | 108.1 |
C1—N1—C34 | 122.7 (3) | C20—C19—C18 | 110.8 (4) |
C1—N1—Ni1 | 110.7 (2) | C20—C19—H19A | 109.5 |
C34—N1—Ni1 | 126.5 (2) | C18—C19—H19A | 109.5 |
C2—N2—C3 | 121.9 (3) | C20—C19—H19B | 109.5 |
C2—N2—Ni1 | 111.3 (2) | C18—C19—H19B | 109.5 |
C3—N2—Ni1 | 126.7 (2) | H19A—C19—H19B | 108.1 |
C9—N3—C16 | 121.0 (3) | C19—C20—C21 | 114.0 (4) |
C9—N3—Ni1 | 131.0 (2) | C19—C20—H20A | 108.8 |
C16—N3—Ni1 | 107.7 (2) | C21—C20—H20A | 108.8 |
C22—N4—C21 | 121.2 (3) | C19—C20—H20B | 108.8 |
C22—N4—Ni1 | 125.4 (2) | C21—C20—H20B | 108.8 |
C21—N4—Ni1 | 111.6 (2) | H20A—C20—H20B | 107.7 |
O1—C1—N1 | 128.6 (3) | N4—C21—C20 | 119.6 (3) |
O1—C1—C2 | 119.6 (3) | N4—C21—C16 | 105.6 (3) |
N1—C1—C2 | 111.8 (3) | C20—C21—C16 | 107.7 (3) |
O2—C2—N2 | 127.6 (4) | N4—C21—H21 | 107.8 |
O2—C2—C1 | 120.4 (3) | C20—C21—H21 | 107.8 |
N2—C2—C1 | 112.0 (3) | C16—C21—H21 | 107.8 |
N2—C3—C4 | 121.3 (3) | N4—C22—C29 | 122.8 (3) |
N2—C3—C8 | 121.2 (3) | N4—C22—C23 | 120.7 (3) |
C4—C3—C8 | 117.4 (3) | C29—C22—C23 | 116.5 (3) |
C5—C4—C3 | 121.8 (4) | C28—C23—C24 | 119.4 (3) |
C5—C4—H4 | 119.1 | C28—C23—C22 | 117.7 (3) |
C3—C4—H4 | 119.1 | C24—C23—C22 | 122.9 (3) |
C6—C5—C4 | 119.6 (4) | C23—C24—C25 | 119.2 (4) |
C6—C5—H5 | 120.2 | C23—C24—H24 | 120.4 |
C4—C5—H5 | 120.2 | C25—C24—H24 | 120.4 |
C7—C6—C5 | 120.9 (4) | C26—C25—C24 | 120.3 (4) |
C7—C6—Cl2 | 119.3 (3) | C26—C25—H25 | 119.9 |
C5—C6—Cl2 | 119.8 (3) | C24—C25—H25 | 119.9 |
C6—C7—C8 | 120.7 (4) | C27—C26—C25 | 120.5 (4) |
C6—C7—H7 | 119.7 | C27—C26—H26 | 119.7 |
C8—C7—H7 | 119.7 | C25—C26—H26 | 119.7 |
C7—C8—C3 | 119.5 (3) | C26—C27—C28 | 120.0 (4) |
C7—C8—C9 | 118.2 (3) | C26—C27—H27 | 120.0 |
C3—C8—C9 | 122.2 (3) | C28—C27—H27 | 120.0 |
N3—C9—C8 | 121.3 (3) | C27—C28—C23 | 120.6 (4) |
N3—C9—C10 | 121.3 (3) | C27—C28—H28 | 119.7 |
C8—C9—C10 | 117.4 (3) | C23—C28—H28 | 119.7 |
C15—C10—C11 | 119.3 (4) | C34—C29—C30 | 118.8 (3) |
C15—C10—C9 | 120.2 (3) | C34—C29—C22 | 124.5 (3) |
C11—C10—C9 | 120.5 (4) | C30—C29—C22 | 116.6 (3) |
C12—C11—C10 | 119.4 (5) | C31—C30—C29 | 121.2 (3) |
C12—C11—H11 | 120.3 | C31—C30—H30 | 119.4 |
C10—C11—H11 | 120.3 | C29—C30—H30 | 119.4 |
C13—C12—C11 | 120.1 (5) | C30—C31—C32 | 121.1 (3) |
C13—C12—H12 | 119.9 | C30—C31—Cl1 | 119.7 (3) |
C11—C12—H12 | 119.9 | C32—C31—Cl1 | 119.2 (3) |
C12—C13—C14 | 120.5 (4) | C31—C32—C33 | 119.1 (3) |
C12—C13—H13 | 119.7 | C31—C32—H32 | 120.4 |
C14—C13—H13 | 119.7 | C33—C32—H32 | 120.4 |
C13—C14—C15 | 119.9 (5) | C32—C33—C34 | 122.3 (3) |
C13—C14—H14 | 120.0 | C32—C33—H33 | 118.8 |
C15—C14—H14 | 120.0 | C34—C33—H33 | 118.8 |
C14—C15—C10 | 120.7 (4) | N1—C34—C33 | 121.2 (3) |
C14—C15—H15 | 119.7 | N1—C34—C29 | 121.2 (3) |
C10—C15—H15 | 119.7 | C33—C34—C29 | 117.5 (3) |
N3—C16—C21 | 106.5 (3) | Cl4—C35—Cl3 | 116.0 (3) |
N3—C16—C17 | 108.0 (3) | Cl4—C35—H35A | 108.3 |
C21—C16—C17 | 113.5 (3) | Cl3—C35—H35A | 108.3 |
N3—C16—H16 | 109.6 | Cl4—C35—H35B | 108.3 |
C21—C16—H16 | 109.6 | Cl3—C35—H35B | 108.3 |
C17—C16—H16 | 109.6 | H35A—C35—H35B | 107.4 |
C18—C17—C16 | 111.3 (3) | Cl5—C36—Cl5i | 112.7 (5) |
C18—C17—H17A | 109.4 | Cl5—C36—H36A | 109.0 |
C16—C17—H17A | 109.4 | Cl5i—C36—H36A | 109.0 |
C18—C17—H17B | 109.4 | Cl5—C36—H36B | 109.0 |
C16—C17—H17B | 109.4 | Cl5i—C36—H36B | 109.0 |
H17A—C17—H17B | 108.0 | H36A—C36—H36B | 107.8 |
| | | |
N3—Ni1—N1—C1 | −48.2 (12) | C15—C10—C11—C12 | 0.0 (6) |
N2—Ni1—N1—C1 | 24.6 (2) | C9—C10—C11—C12 | 179.9 (4) |
N4—Ni1—N1—C1 | −160.6 (2) | C10—C11—C12—C13 | 0.3 (7) |
N3—Ni1—N1—C34 | 128.3 (11) | C11—C12—C13—C14 | −0.2 (7) |
N2—Ni1—N1—C34 | −158.9 (3) | C12—C13—C14—C15 | −0.1 (7) |
N4—Ni1—N1—C34 | 15.9 (3) | C13—C14—C15—C10 | 0.4 (7) |
N3—Ni1—N2—C2 | 150.0 (3) | C11—C10—C15—C14 | −0.4 (6) |
N1—Ni1—N2—C2 | −24.1 (3) | C9—C10—C15—C14 | 179.7 (4) |
N4—Ni1—N2—C2 | −131.8 (12) | C9—N3—C16—C21 | 137.1 (3) |
N3—Ni1—N2—C3 | −26.4 (3) | Ni1—N3—C16—C21 | −48.2 (3) |
N1—Ni1—N2—C3 | 159.5 (3) | C9—N3—C16—C17 | −100.7 (4) |
N4—Ni1—N2—C3 | 51.8 (14) | Ni1—N3—C16—C17 | 74.0 (3) |
N2—Ni1—N3—C9 | 17.7 (3) | N3—C16—C17—C18 | −173.4 (3) |
N1—Ni1—N3—C9 | 90.3 (12) | C21—C16—C17—C18 | −55.6 (4) |
N4—Ni1—N3—C9 | −156.9 (3) | C16—C17—C18—C19 | 53.7 (5) |
N2—Ni1—N3—C16 | −156.2 (2) | C17—C18—C19—C20 | −54.4 (5) |
N1—Ni1—N3—C16 | −83.7 (12) | C18—C19—C20—C21 | 57.4 (4) |
N4—Ni1—N3—C16 | 29.1 (2) | C22—N4—C21—C20 | 50.6 (5) |
N3—Ni1—N4—C22 | 161.6 (3) | Ni1—N4—C21—C20 | −143.8 (3) |
N2—Ni1—N4—C22 | 83.2 (13) | C22—N4—C21—C16 | 172.1 (3) |
N1—Ni1—N4—C22 | −24.1 (3) | Ni1—N4—C21—C16 | −22.3 (3) |
N3—Ni1—N4—C21 | −3.3 (2) | C19—C20—C21—N4 | 64.4 (4) |
N2—Ni1—N4—C21 | −81.7 (13) | C19—C20—C21—C16 | −55.9 (4) |
N1—Ni1—N4—C21 | 171.0 (2) | N3—C16—C21—N4 | 44.5 (3) |
C34—N1—C1—O1 | −13.8 (6) | C17—C16—C21—N4 | −74.2 (4) |
Ni1—N1—C1—O1 | 162.9 (3) | N3—C16—C21—C20 | 173.3 (3) |
C34—N1—C1—C2 | 163.8 (3) | C17—C16—C21—C20 | 54.6 (4) |
Ni1—N1—C1—C2 | −19.5 (4) | C21—N4—C22—C29 | −176.5 (3) |
C3—N2—C2—O2 | 12.8 (6) | Ni1—N4—C22—C29 | 20.0 (5) |
Ni1—N2—C2—O2 | −163.8 (4) | C21—N4—C22—C23 | 6.4 (5) |
C3—N2—C2—C1 | −165.2 (3) | Ni1—N4—C22—C23 | −157.1 (3) |
Ni1—N2—C2—C1 | 18.2 (4) | N4—C22—C23—C28 | 69.8 (4) |
O1—C1—C2—O2 | 0.7 (6) | C29—C22—C23—C28 | −107.5 (4) |
N1—C1—C2—O2 | −177.2 (4) | N4—C22—C23—C24 | −111.1 (4) |
O1—C1—C2—N2 | 178.8 (3) | C29—C22—C23—C24 | 71.6 (4) |
N1—C1—C2—N2 | 1.0 (4) | C28—C23—C24—C25 | −1.4 (5) |
C2—N2—C3—C4 | 27.9 (5) | C22—C23—C24—C25 | 179.5 (3) |
Ni1—N2—C3—C4 | −156.1 (3) | C23—C24—C25—C26 | 1.0 (6) |
C2—N2—C3—C8 | −155.9 (3) | C24—C25—C26—C27 | −0.1 (6) |
Ni1—N2—C3—C8 | 20.1 (5) | C25—C26—C27—C28 | −0.5 (6) |
N2—C3—C4—C5 | 178.2 (4) | C26—C27—C28—C23 | 0.1 (6) |
C8—C3—C4—C5 | 1.9 (6) | C24—C23—C28—C27 | 0.9 (5) |
C3—C4—C5—C6 | 0.4 (6) | C22—C23—C28—C27 | 180.0 (3) |
C4—C5—C6—C7 | −2.7 (6) | N4—C22—C29—C34 | −0.8 (5) |
C4—C5—C6—Cl2 | 176.9 (3) | C23—C22—C29—C34 | 176.4 (3) |
C5—C6—C7—C8 | 2.6 (6) | N4—C22—C29—C30 | 176.9 (3) |
Cl2—C6—C7—C8 | −177.0 (3) | C23—C22—C29—C30 | −5.9 (5) |
C6—C7—C8—C3 | −0.2 (5) | C34—C29—C30—C31 | 1.3 (5) |
C6—C7—C8—C9 | 177.6 (3) | C22—C29—C30—C31 | −176.5 (3) |
N2—C3—C8—C7 | −178.3 (3) | C29—C30—C31—C32 | −1.2 (6) |
C4—C3—C8—C7 | −1.9 (5) | C29—C30—C31—Cl1 | 178.3 (3) |
N2—C3—C8—C9 | 3.9 (5) | C30—C31—C32—C33 | 0.9 (6) |
C4—C3—C8—C9 | −179.7 (3) | Cl1—C31—C32—C33 | −178.6 (3) |
C16—N3—C9—C8 | 171.5 (3) | C31—C32—C33—C34 | −0.8 (6) |
Ni1—N3—C9—C8 | −1.8 (5) | C1—N1—C34—C33 | −11.9 (5) |
C16—N3—C9—C10 | −9.6 (5) | Ni1—N1—C34—C33 | 172.0 (3) |
Ni1—N3—C9—C10 | 177.2 (3) | C1—N1—C34—C29 | 172.5 (3) |
C7—C8—C9—N3 | 168.8 (3) | Ni1—N1—C34—C29 | −3.7 (5) |
C3—C8—C9—N3 | −13.4 (5) | C32—C33—C34—N1 | −174.8 (4) |
C7—C8—C9—C10 | −10.2 (5) | C32—C33—C34—C29 | 1.0 (6) |
C3—C8—C9—C10 | 167.6 (3) | C30—C29—C34—N1 | 174.6 (3) |
N3—C9—C10—C15 | −70.3 (5) | C22—C29—C34—N1 | −7.7 (5) |
C8—C9—C10—C15 | 108.7 (4) | C30—C29—C34—C33 | −1.2 (5) |
N3—C9—C10—C11 | 109.8 (4) | C22—C29—C34—C33 | 176.4 (3) |
C8—C9—C10—C11 | −71.2 (5) | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···Cl1ii | 0.97 | 2.93 | 3.764 (5) | 145 |
C20—H20A···Cl1ii | 0.97 | 2.85 | 3.720 (5) | 150 |
C26—H26···O1iii | 0.93 | 2.61 | 3.452 (6) | 151 |
C27—H27···O2iii | 0.93 | 2.49 | 3.223 (5) | 136 |
C35—H35A···O2iii | 0.97 | 2.56 | 3.395 (7) | 145 |
Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x, y+1, z. |