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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034628/sj6134sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034628/sj6134Isup2.hkl
Contains datablock I

CCDC reference: 259898

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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[20.4.0.04,9.012,17]hexacosa- 2,10,12,14,16,22,24,26-octaene-19,20-dionato(2-)]nickel(II) dichloromethane sesquisolvate top
Crystal data top
[Ni(C34H26Cl2N4O2)]·1.5CH2Cl2F(000) = 3192
Mr = 779.59Dx = 1.542 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 26.745 (7) ÅCell parameters from 985 reflections
b = 12.520 (3) Åθ = 3.2–25.4°
c = 22.820 (6) ŵ = 1.02 mm1
β = 118.454 (4)°T = 293 K
V = 6718 (3) Å3Block, red
Z = 80.22 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5930 independent reflections
Radiation source: fine-focus sealed tube4119 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3131
Tmin = 0.754, Tmax = 0.833k = 1014
17189 measured reflectionsl = 2427
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-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 parametersΔρmax = 0.80 e Å3
9 restraintsΔρmin = 0.78 e Å3
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
xyzUiso*/UeqOcc. (<1)
Ni10.136067 (19)0.24467 (3)0.28015 (2)0.02877 (14)
Cl10.21169 (5)0.44373 (9)0.60820 (5)0.0550 (3)
Cl20.08844 (4)0.05545 (9)0.03365 (5)0.0547 (3)
O10.16488 (12)0.0200 (2)0.40832 (13)0.0477 (7)
O20.10162 (14)0.0542 (2)0.28016 (15)0.0605 (8)
N10.15136 (12)0.1917 (2)0.36341 (14)0.0303 (7)
N20.09390 (13)0.1211 (2)0.24467 (15)0.0341 (7)
N30.12618 (12)0.2863 (2)0.19714 (14)0.0306 (7)
N40.17227 (12)0.3772 (2)0.31286 (13)0.0308 (7)
C10.14673 (16)0.0826 (3)0.36179 (19)0.0349 (8)
C20.11172 (16)0.0407 (3)0.29040 (19)0.0373 (9)
C30.05147 (15)0.1057 (3)0.17928 (18)0.0339 (8)
C40.00876 (17)0.0280 (3)0.1632 (2)0.0441 (10)
H40.00970.01510.19690.053*
C50.03418 (17)0.0142 (3)0.0991 (2)0.0457 (10)
H50.06200.03740.08980.055*
C60.03576 (15)0.0770 (3)0.04887 (19)0.0399 (9)
C70.00338 (16)0.1559 (3)0.06214 (18)0.0386 (9)
H70.00070.19940.02770.046*
C80.04760 (15)0.1719 (3)0.12703 (18)0.0330 (8)
C90.08988 (15)0.2555 (3)0.13780 (17)0.0317 (8)
C100.08851 (16)0.3049 (3)0.07741 (17)0.0378 (9)
C110.10593 (18)0.2469 (4)0.0383 (2)0.0528 (11)
H110.11860.17690.04950.063*
C120.1042 (2)0.2945 (5)0.0178 (2)0.0676 (14)
H120.11560.25610.04430.081*
C130.0858 (2)0.3976 (5)0.0340 (2)0.0707 (16)
H130.08480.42900.07140.085*
C140.0687 (2)0.4548 (4)0.0045 (2)0.0664 (14)
H140.05630.52490.00680.080*
C150.06988 (17)0.4084 (3)0.0599 (2)0.0491 (11)
H150.05800.44730.08570.059*
C160.17342 (14)0.3592 (3)0.20815 (17)0.0309 (8)
H160.16480.39560.16640.037*
C170.22718 (17)0.2923 (3)0.2310 (2)0.0465 (10)
H17A0.23250.24850.26860.056*
H17B0.22290.24520.19520.056*
C180.27923 (18)0.3628 (4)0.2513 (2)0.0633 (13)
H18A0.27640.39920.21230.076*
H18B0.31320.31880.26960.076*
C190.2839 (2)0.4449 (4)0.3029 (2)0.0727 (16)
H19A0.29160.40870.34400.087*
H19B0.31530.49290.31240.087*
C200.2297 (2)0.5083 (3)0.2780 (2)0.0531 (12)
H20A0.22420.54910.23930.064*
H20B0.23370.55870.31230.064*
C210.17726 (16)0.4407 (3)0.25950 (16)0.0334 (8)
H210.14390.48740.23810.040*
C220.18044 (14)0.4219 (3)0.36823 (16)0.0291 (8)
C230.18909 (16)0.5400 (3)0.37790 (17)0.0320 (8)
C240.24087 (18)0.5857 (3)0.42269 (19)0.0437 (10)
H240.27210.54270.44860.052*
C250.2454 (2)0.6966 (4)0.4282 (2)0.0570 (13)
H250.27990.72790.45750.068*
C260.1986 (2)0.7602 (3)0.3904 (2)0.0597 (13)
H260.20200.83410.39440.072*
C270.1479 (2)0.7155 (3)0.3474 (2)0.0552 (12)
H270.11660.75890.32240.066*
C280.14273 (17)0.6056 (3)0.34081 (19)0.0401 (9)
H280.10790.57540.31130.048*
C290.17913 (14)0.3614 (3)0.42301 (16)0.0293 (8)
C300.19155 (15)0.4193 (3)0.48156 (17)0.0337 (8)
H300.19790.49250.48280.040*
C310.19439 (16)0.3698 (3)0.53612 (17)0.0370 (9)
C320.18430 (18)0.2624 (3)0.53578 (19)0.0463 (10)
H320.18580.22950.57310.056*
C330.17185 (17)0.2038 (3)0.47932 (19)0.0421 (9)
H330.16550.13080.47950.051*
C340.16838 (14)0.2506 (3)0.42134 (17)0.0309 (8)
Cl30.09208 (8)0.67923 (13)0.13103 (10)0.1111 (6)
Cl40.01510 (8)0.71881 (19)0.18506 (8)0.1294 (8)
C350.0547 (3)0.7702 (4)0.1514 (3)0.0890 (18)
H35A0.08150.82090.18280.107*
H35B0.02960.80950.11140.107*
Cl50.99241 (14)0.4072 (3)0.18441 (16)0.2028 (14)
C361.00000.3322 (6)0.25000.150 (6)
H36A1.03310.28660.26410.180*0.50
H36B0.96690.28660.23590.180*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0386 (3)0.0235 (2)0.0259 (2)0.0022 (2)0.0168 (2)0.00044 (19)
Cl10.0744 (8)0.0645 (7)0.0340 (5)0.0013 (6)0.0321 (5)0.0078 (5)
Cl20.0441 (6)0.0606 (7)0.0444 (6)0.0059 (5)0.0089 (5)0.0157 (5)
O10.0667 (19)0.0280 (14)0.0427 (16)0.0035 (13)0.0214 (15)0.0100 (12)
O20.081 (2)0.0253 (15)0.0553 (19)0.0050 (14)0.0159 (16)0.0004 (13)
N10.0379 (17)0.0235 (16)0.0288 (16)0.0003 (13)0.0154 (14)0.0035 (12)
N20.0421 (18)0.0254 (16)0.0346 (17)0.0043 (13)0.0180 (15)0.0007 (13)
N30.0383 (17)0.0279 (15)0.0289 (16)0.0020 (13)0.0188 (14)0.0020 (12)
N40.0439 (18)0.0261 (16)0.0242 (15)0.0008 (13)0.0176 (14)0.0031 (12)
C10.041 (2)0.027 (2)0.041 (2)0.0013 (16)0.0226 (18)0.0053 (17)
C20.040 (2)0.028 (2)0.041 (2)0.0005 (16)0.0177 (18)0.0017 (17)
C30.037 (2)0.0308 (19)0.035 (2)0.0034 (16)0.0187 (17)0.0066 (16)
C40.049 (2)0.038 (2)0.046 (2)0.0072 (18)0.023 (2)0.0015 (18)
C50.038 (2)0.042 (2)0.056 (3)0.0124 (18)0.021 (2)0.010 (2)
C60.032 (2)0.042 (2)0.039 (2)0.0004 (17)0.0113 (17)0.0097 (18)
C70.042 (2)0.041 (2)0.033 (2)0.0004 (18)0.0176 (18)0.0039 (17)
C80.034 (2)0.031 (2)0.034 (2)0.0009 (15)0.0162 (17)0.0051 (16)
C90.039 (2)0.0296 (19)0.0274 (18)0.0010 (16)0.0169 (16)0.0036 (16)
C100.039 (2)0.046 (2)0.0238 (19)0.0121 (18)0.0107 (17)0.0029 (17)
C110.062 (3)0.064 (3)0.037 (2)0.009 (2)0.028 (2)0.008 (2)
C120.060 (3)0.113 (5)0.038 (3)0.016 (3)0.030 (2)0.015 (3)
C130.056 (3)0.115 (5)0.032 (3)0.028 (3)0.013 (2)0.015 (3)
C140.058 (3)0.077 (4)0.045 (3)0.005 (3)0.010 (2)0.022 (3)
C150.051 (3)0.050 (3)0.038 (2)0.003 (2)0.015 (2)0.0065 (19)
C160.036 (2)0.0316 (19)0.0249 (18)0.0041 (15)0.0145 (16)0.0014 (15)
C170.050 (3)0.043 (2)0.053 (3)0.0076 (19)0.030 (2)0.007 (2)
C180.039 (3)0.079 (3)0.068 (3)0.007 (2)0.023 (2)0.030 (3)
C190.057 (3)0.103 (4)0.040 (3)0.041 (3)0.008 (2)0.012 (3)
C200.084 (4)0.051 (3)0.032 (2)0.031 (2)0.034 (2)0.0076 (19)
C210.049 (2)0.0264 (18)0.0258 (18)0.0030 (16)0.0187 (17)0.0050 (15)
C220.032 (2)0.0272 (19)0.0274 (19)0.0022 (14)0.0137 (16)0.0039 (15)
C230.048 (2)0.0260 (19)0.0257 (18)0.0026 (16)0.0209 (17)0.0026 (14)
C240.056 (3)0.044 (2)0.032 (2)0.0042 (19)0.0210 (19)0.0044 (17)
C250.082 (3)0.052 (3)0.048 (3)0.035 (3)0.040 (3)0.027 (2)
C260.111 (4)0.031 (2)0.058 (3)0.009 (3)0.056 (3)0.006 (2)
C270.093 (4)0.033 (2)0.050 (3)0.014 (2)0.042 (3)0.008 (2)
C280.052 (2)0.030 (2)0.039 (2)0.0004 (17)0.023 (2)0.0017 (17)
C290.035 (2)0.0287 (19)0.0271 (18)0.0048 (15)0.0171 (16)0.0012 (15)
C300.040 (2)0.032 (2)0.033 (2)0.0020 (16)0.0210 (17)0.0011 (16)
C310.043 (2)0.046 (2)0.0272 (19)0.0032 (17)0.0206 (17)0.0036 (17)
C320.065 (3)0.050 (3)0.031 (2)0.003 (2)0.028 (2)0.0077 (19)
C330.061 (3)0.032 (2)0.039 (2)0.0029 (19)0.028 (2)0.0058 (17)
C340.0347 (19)0.0320 (19)0.0273 (18)0.0025 (16)0.0158 (15)0.0022 (16)
Cl30.1355 (15)0.0722 (10)0.1295 (15)0.0089 (10)0.0662 (13)0.0233 (10)
Cl40.0990 (13)0.210 (2)0.0677 (10)0.0641 (14)0.0302 (9)0.0138 (12)
C350.103 (5)0.077 (4)0.100 (5)0.000 (3)0.059 (4)0.004 (3)
Cl50.217 (3)0.236 (3)0.194 (3)0.100 (3)0.130 (2)0.046 (2)
C360.100 (7)0.048 (5)0.35 (2)0.0000.147 (11)0.000
C220.0335 (17)0.0266 (17)0.0257 (17)0.0013 (13)0.0018 (13)0.0134 (14)
C230.0295 (16)0.0204 (15)0.0199 (15)0.0013 (12)0.0008 (12)0.0090 (13)
C240.0234 (15)0.0239 (16)0.0242 (16)0.0015 (12)0.0038 (12)0.0074 (14)
O200.0344 (14)0.0505 (17)0.0646 (18)0.0028 (12)0.0126 (12)0.0052 (14)
Geometric parameters (Å, º) top
Ni1—N31.858 (3)C17—H17A0.9700
Ni1—N21.858 (3)C17—H17B0.9700
Ni1—N11.865 (3)C18—C191.524 (7)
Ni1—N41.887 (3)C18—H18A0.9700
Cl1—C311.747 (4)C18—H18B0.9700
Cl2—C61.754 (4)C19—C201.507 (7)
O1—C11.219 (4)C19—H19A0.9700
O2—C21.217 (4)C19—H19B0.9700
N1—C11.370 (4)C20—C211.516 (5)
N1—C341.387 (4)C20—H20A0.9700
N2—C21.361 (4)C20—H20B0.9700
N2—C31.392 (4)C21—H210.9800
N3—C91.293 (4)C22—C291.476 (4)
N3—C161.480 (4)C22—C231.497 (5)
N4—C221.301 (4)C23—C281.389 (5)
N4—C211.512 (4)C23—C241.393 (5)
C1—C21.534 (5)C24—C251.394 (6)
C3—C41.410 (5)C24—H240.9300
C3—C81.414 (5)C25—C261.383 (7)
C4—C51.374 (5)C25—H250.9300
C4—H40.9300C26—C271.360 (7)
C5—C61.375 (5)C26—H260.9300
C5—H50.9300C27—C281.384 (5)
C6—C71.364 (5)C27—H270.9300
C7—C81.401 (5)C28—H280.9300
C7—H70.9300C29—C341.414 (5)
C8—C91.474 (5)C29—C301.413 (5)
C9—C101.495 (5)C30—C311.360 (5)
C10—C151.378 (5)C30—H300.9300
C10—C111.392 (5)C31—C321.371 (5)
C11—C121.392 (6)C32—C331.378 (5)
C11—H110.9300C32—H320.9300
C12—C131.368 (7)C33—C341.409 (5)
C12—H120.9300C33—H330.9300
C13—C141.368 (7)Cl3—C351.718 (5)
C13—H130.9300Cl4—C351.704 (5)
C14—C151.378 (6)C35—H35A0.9700
C14—H140.9300C35—H35B0.9700
C15—H150.9300Cl5—C361.695 (4)
C16—C211.520 (5)C36—Cl5i1.695 (4)
C16—C171.525 (5)C36—H36A0.9700
C16—H160.9800C36—H36B0.9700
C17—C181.522 (6)
N3—Ni1—N291.55 (12)C17—C18—C19110.6 (4)
N3—Ni1—N1173.81 (12)C17—C18—H18A109.5
N2—Ni1—N186.60 (12)C19—C18—H18A109.5
N3—Ni1—N487.35 (12)C17—C18—H18B109.5
N2—Ni1—N4174.56 (13)C19—C18—H18B109.5
N1—Ni1—N495.03 (12)H18A—C18—H18B108.1
C1—N1—C34122.7 (3)C20—C19—C18110.8 (4)
C1—N1—Ni1110.7 (2)C20—C19—H19A109.5
C34—N1—Ni1126.5 (2)C18—C19—H19A109.5
C2—N2—C3121.9 (3)C20—C19—H19B109.5
C2—N2—Ni1111.3 (2)C18—C19—H19B109.5
C3—N2—Ni1126.7 (2)H19A—C19—H19B108.1
C9—N3—C16121.0 (3)C19—C20—C21114.0 (4)
C9—N3—Ni1131.0 (2)C19—C20—H20A108.8
C16—N3—Ni1107.7 (2)C21—C20—H20A108.8
C22—N4—C21121.2 (3)C19—C20—H20B108.8
C22—N4—Ni1125.4 (2)C21—C20—H20B108.8
C21—N4—Ni1111.6 (2)H20A—C20—H20B107.7
O1—C1—N1128.6 (3)N4—C21—C20119.6 (3)
O1—C1—C2119.6 (3)N4—C21—C16105.6 (3)
N1—C1—C2111.8 (3)C20—C21—C16107.7 (3)
O2—C2—N2127.6 (4)N4—C21—H21107.8
O2—C2—C1120.4 (3)C20—C21—H21107.8
N2—C2—C1112.0 (3)C16—C21—H21107.8
N2—C3—C4121.3 (3)N4—C22—C29122.8 (3)
N2—C3—C8121.2 (3)N4—C22—C23120.7 (3)
C4—C3—C8117.4 (3)C29—C22—C23116.5 (3)
C5—C4—C3121.8 (4)C28—C23—C24119.4 (3)
C5—C4—H4119.1C28—C23—C22117.7 (3)
C3—C4—H4119.1C24—C23—C22122.9 (3)
C6—C5—C4119.6 (4)C23—C24—C25119.2 (4)
C6—C5—H5120.2C23—C24—H24120.4
C4—C5—H5120.2C25—C24—H24120.4
C7—C6—C5120.9 (4)C26—C25—C24120.3 (4)
C7—C6—Cl2119.3 (3)C26—C25—H25119.9
C5—C6—Cl2119.8 (3)C24—C25—H25119.9
C6—C7—C8120.7 (4)C27—C26—C25120.5 (4)
C6—C7—H7119.7C27—C26—H26119.7
C8—C7—H7119.7C25—C26—H26119.7
C7—C8—C3119.5 (3)C26—C27—C28120.0 (4)
C7—C8—C9118.2 (3)C26—C27—H27120.0
C3—C8—C9122.2 (3)C28—C27—H27120.0
N3—C9—C8121.3 (3)C27—C28—C23120.6 (4)
N3—C9—C10121.3 (3)C27—C28—H28119.7
C8—C9—C10117.4 (3)C23—C28—H28119.7
C15—C10—C11119.3 (4)C34—C29—C30118.8 (3)
C15—C10—C9120.2 (3)C34—C29—C22124.5 (3)
C11—C10—C9120.5 (4)C30—C29—C22116.6 (3)
C12—C11—C10119.4 (5)C31—C30—C29121.2 (3)
C12—C11—H11120.3C31—C30—H30119.4
C10—C11—H11120.3C29—C30—H30119.4
C13—C12—C11120.1 (5)C30—C31—C32121.1 (3)
C13—C12—H12119.9C30—C31—Cl1119.7 (3)
C11—C12—H12119.9C32—C31—Cl1119.2 (3)
C12—C13—C14120.5 (4)C31—C32—C33119.1 (3)
C12—C13—H13119.7C31—C32—H32120.4
C14—C13—H13119.7C33—C32—H32120.4
C13—C14—C15119.9 (5)C32—C33—C34122.3 (3)
C13—C14—H14120.0C32—C33—H33118.8
C15—C14—H14120.0C34—C33—H33118.8
C14—C15—C10120.7 (4)N1—C34—C33121.2 (3)
C14—C15—H15119.7N1—C34—C29121.2 (3)
C10—C15—H15119.7C33—C34—C29117.5 (3)
N3—C16—C21106.5 (3)Cl4—C35—Cl3116.0 (3)
N3—C16—C17108.0 (3)Cl4—C35—H35A108.3
C21—C16—C17113.5 (3)Cl3—C35—H35A108.3
N3—C16—H16109.6Cl4—C35—H35B108.3
C21—C16—H16109.6Cl3—C35—H35B108.3
C17—C16—H16109.6H35A—C35—H35B107.4
C18—C17—C16111.3 (3)Cl5—C36—Cl5i112.7 (5)
C18—C17—H17A109.4Cl5—C36—H36A109.0
C16—C17—H17A109.4Cl5i—C36—H36A109.0
C18—C17—H17B109.4Cl5—C36—H36B109.0
C16—C17—H17B109.4Cl5i—C36—H36B109.0
H17A—C17—H17B108.0H36A—C36—H36B107.8
N3—Ni1—N1—C148.2 (12)C15—C10—C11—C120.0 (6)
N2—Ni1—N1—C124.6 (2)C9—C10—C11—C12179.9 (4)
N4—Ni1—N1—C1160.6 (2)C10—C11—C12—C130.3 (7)
N3—Ni1—N1—C34128.3 (11)C11—C12—C13—C140.2 (7)
N2—Ni1—N1—C34158.9 (3)C12—C13—C14—C150.1 (7)
N4—Ni1—N1—C3415.9 (3)C13—C14—C15—C100.4 (7)
N3—Ni1—N2—C2150.0 (3)C11—C10—C15—C140.4 (6)
N1—Ni1—N2—C224.1 (3)C9—C10—C15—C14179.7 (4)
N4—Ni1—N2—C2131.8 (12)C9—N3—C16—C21137.1 (3)
N3—Ni1—N2—C326.4 (3)Ni1—N3—C16—C2148.2 (3)
N1—Ni1—N2—C3159.5 (3)C9—N3—C16—C17100.7 (4)
N4—Ni1—N2—C351.8 (14)Ni1—N3—C16—C1774.0 (3)
N2—Ni1—N3—C917.7 (3)N3—C16—C17—C18173.4 (3)
N1—Ni1—N3—C990.3 (12)C21—C16—C17—C1855.6 (4)
N4—Ni1—N3—C9156.9 (3)C16—C17—C18—C1953.7 (5)
N2—Ni1—N3—C16156.2 (2)C17—C18—C19—C2054.4 (5)
N1—Ni1—N3—C1683.7 (12)C18—C19—C20—C2157.4 (4)
N4—Ni1—N3—C1629.1 (2)C22—N4—C21—C2050.6 (5)
N3—Ni1—N4—C22161.6 (3)Ni1—N4—C21—C20143.8 (3)
N2—Ni1—N4—C2283.2 (13)C22—N4—C21—C16172.1 (3)
N1—Ni1—N4—C2224.1 (3)Ni1—N4—C21—C1622.3 (3)
N3—Ni1—N4—C213.3 (2)C19—C20—C21—N464.4 (4)
N2—Ni1—N4—C2181.7 (13)C19—C20—C21—C1655.9 (4)
N1—Ni1—N4—C21171.0 (2)N3—C16—C21—N444.5 (3)
C34—N1—C1—O113.8 (6)C17—C16—C21—N474.2 (4)
Ni1—N1—C1—O1162.9 (3)N3—C16—C21—C20173.3 (3)
C34—N1—C1—C2163.8 (3)C17—C16—C21—C2054.6 (4)
Ni1—N1—C1—C219.5 (4)C21—N4—C22—C29176.5 (3)
C3—N2—C2—O212.8 (6)Ni1—N4—C22—C2920.0 (5)
Ni1—N2—C2—O2163.8 (4)C21—N4—C22—C236.4 (5)
C3—N2—C2—C1165.2 (3)Ni1—N4—C22—C23157.1 (3)
Ni1—N2—C2—C118.2 (4)N4—C22—C23—C2869.8 (4)
O1—C1—C2—O20.7 (6)C29—C22—C23—C28107.5 (4)
N1—C1—C2—O2177.2 (4)N4—C22—C23—C24111.1 (4)
O1—C1—C2—N2178.8 (3)C29—C22—C23—C2471.6 (4)
N1—C1—C2—N21.0 (4)C28—C23—C24—C251.4 (5)
C2—N2—C3—C427.9 (5)C22—C23—C24—C25179.5 (3)
Ni1—N2—C3—C4156.1 (3)C23—C24—C25—C261.0 (6)
C2—N2—C3—C8155.9 (3)C24—C25—C26—C270.1 (6)
Ni1—N2—C3—C820.1 (5)C25—C26—C27—C280.5 (6)
N2—C3—C4—C5178.2 (4)C26—C27—C28—C230.1 (6)
C8—C3—C4—C51.9 (6)C24—C23—C28—C270.9 (5)
C3—C4—C5—C60.4 (6)C22—C23—C28—C27180.0 (3)
C4—C5—C6—C72.7 (6)N4—C22—C29—C340.8 (5)
C4—C5—C6—Cl2176.9 (3)C23—C22—C29—C34176.4 (3)
C5—C6—C7—C82.6 (6)N4—C22—C29—C30176.9 (3)
Cl2—C6—C7—C8177.0 (3)C23—C22—C29—C305.9 (5)
C6—C7—C8—C30.2 (5)C34—C29—C30—C311.3 (5)
C6—C7—C8—C9177.6 (3)C22—C29—C30—C31176.5 (3)
N2—C3—C8—C7178.3 (3)C29—C30—C31—C321.2 (6)
C4—C3—C8—C71.9 (5)C29—C30—C31—Cl1178.3 (3)
N2—C3—C8—C93.9 (5)C30—C31—C32—C330.9 (6)
C4—C3—C8—C9179.7 (3)Cl1—C31—C32—C33178.6 (3)
C16—N3—C9—C8171.5 (3)C31—C32—C33—C340.8 (6)
Ni1—N3—C9—C81.8 (5)C1—N1—C34—C3311.9 (5)
C16—N3—C9—C109.6 (5)Ni1—N1—C34—C33172.0 (3)
Ni1—N3—C9—C10177.2 (3)C1—N1—C34—C29172.5 (3)
C7—C8—C9—N3168.8 (3)Ni1—N1—C34—C293.7 (5)
C3—C8—C9—N313.4 (5)C32—C33—C34—N1174.8 (4)
C7—C8—C9—C1010.2 (5)C32—C33—C34—C291.0 (6)
C3—C8—C9—C10167.6 (3)C30—C29—C34—N1174.6 (3)
N3—C9—C10—C1570.3 (5)C22—C29—C34—N17.7 (5)
C8—C9—C10—C15108.7 (4)C30—C29—C34—C331.2 (5)
N3—C9—C10—C11109.8 (4)C22—C29—C34—C33176.4 (3)
C8—C9—C10—C1171.2 (5)
Symmetry code: (i) x+2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···Cl1ii0.972.933.764 (5)145
C20—H20A···Cl1ii0.972.853.720 (5)150
C26—H26···O1iii0.932.613.452 (6)151
C27—H27···O2iii0.932.493.223 (5)136
C35—H35A···O2iii0.972.563.395 (7)145
Symmetry codes: (ii) x, y+1, z1/2; (iii) x, y+1, z.
 

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