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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m751–m752.
Published online 2009 June 10. doi:  10.1107/S1600536809021163
PMCID: PMC2969312

Bis[1,3-bis­(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane]nickel(II) dipicrate–dimethyl­formamide–ethanol (1/2/0.25)

Abstract

In the title compound, [Ni(C30H26N4O)2](C6H2N3O7)2·2C3H7NO·0.25CH3CH2OH, the NiII ion is coordinated in a distorted octa­hedral environment by four N atoms and two O atoms from two tridendate 1,3-bis­(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane ligands. The crystal structure is stabilized by weak inter­molecular C—H(...)O hydrogen bonds and weak π–π stacking inter­actions [centroid–centroid distance 3.501 (3) Å]. As well as the cation, two anions and two dimethyl­formamide solvent mol­ecules, the asymmetric unit also contains an ethanol solvent molecule with 0.25 occupancy.

Related literature

For background to the applications of bis­(2-benzimidazol­yl)alkanes and their derivatives, see: Hendriks et al. (1982 [triangle]); Piquet et al. (1995 [triangle]); Roderick et al. (1972 [triangle]); Wu et al. (2005 [triangle]); van Berkel et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m751-scheme1.jpg

Experimental

Crystal data

  • [Ni(C30H26N4O)2](C6H2N3O7)2·2C3H7NO·0.25C2H6O
  • M r = 1589.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m751-efi1.jpg
  • a = 16.6265 (4) Å
  • b = 18.1735 (5) Å
  • c = 26.6287 (8) Å
  • β = 107.513 (1)°
  • V = 7673.2 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 153 K
  • 0.16 × 0.12 × 0.11 mm

Data collection

  • Rigaku R-AXIS SPIDER diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.948, T max = 0.964
  • 57512 measured reflections
  • 13620 independent reflections
  • 7422 reflections with I > 2σ(I)
  • R int = 0.100

Refinement

  • R[F 2 > 2σ(F 2)] = 0.093
  • wR(F 2) = 0.290
  • S = 1.14
  • 13620 reflections
  • 1031 parameters
  • 33 restraints
  • H-atom parameters constrained
  • Δρmax = 1.47 e Å−3
  • Δρmin = −0.70 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021163/lh2826sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021163/lh2826Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (No. 3YS061-A25–023) and ‘Long Yuan Qing Nian’ of Gansu Province is also acknowledged

supplementary crystallographic information

Comment

There is widespread interest in bis(2-benzimidazolyl)alkanes and their derivatives because of their wide-ranging anti-virus activity (Roderick et al., 1972), their importance in selective ion-exchange resins (van Berkel et al., 1995), and the possibility of forming supramolecular aggregates with d10 metal ions in which discrete macrocycles, 1, 2 and 3-D architectures have been generated (Piquet et al. 1995). We have been interested in utilizing benzimidazolyl substituted tripodal ligands with nitrogen cores to construct supramolecules, which could provide hydrogen bond donor NH groups and π–π stacking interactions (Hendriks et al., 1982). In our work, efforts are focused on the tridentate ligand, 1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxopropane, which is similar to the histidine imidazole ligand in its coordination aspects (Wu et al. 2005). Since the two arms of this type of ligand can each rotate freely about an O(apical)-C bond, multicomponent complexes or coordination polymeric networks may be expected to form from the assembly of this ligand with metal ions of low coordination number. Herein, the crystal structure of the title compound is presented. The molecular structure of the cation is shown in Fig. 1. The NiII ion is coordinated in a disotorted octahedral environment inolving four N atoms and two O atoms from two tridendate ligands with the axial sites occupied by two oxygen atoms. The crystal structure is stabilized by weak intermolecular C-H···O hydrogen bonds as well as weak π–π stacking interactions with a centroid to centroid distance of 3.501 (3) Å between two benzimidazole ring systems related by the symmetry operator (1-x,-1/2+y,1/2-z).

Experimental

Reagents and solvents used were of commercially available quality. To a strred solution of 1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxopropane (183.2 mg, 0.4 mmol) in hot MeOH (10 ml) was added Ni(C6H2N3O7)2 (102.9 mg, 0.2 mmol) in MeOH (5 ml). A green crystalline product formed rapidly. The precipitate was filtered off, washed with methanol and absolute ethanol, and dried in vacuo. The dried precipitate was dissolved in DMF to form a green solution that was allowed to evaporate at room temperature. The green crystals suitable for X-ray diffraction studies were obtained after three weeks (Yield, 64%). Elemental analysis - found: C, 59.30; H, 4.51; N, 14.14; calc. for C78.5H71.5N16O18.25Ni, C, 59.31; H, 4.53; N, 14.10%.

Refinement

All H atoms were found in difference electron maps and were subsequently refined in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq or Uiso(H) = 1.5 Ueq for methyl C atoms. The abundance of solvent which is loosely held in the crystal lattice is probably the reason for the lower than normal precision of this structure.

Figures

Fig. 1.
The molecular structure of the cation. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.
Fig. 2.
Part of the crystal structure with weak hydrogen bonds shown as dashed lines. For clarity the solvent molecules are not included.

Crystal data

[Ni(C30H26N4O)2](C6H2N3O7)2·2C3H7NO·0.25C2H6OF(000) = 3314
Mr = 1589.73Dx = 1.376 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7422 reflections
a = 16.6265 (4) Åθ = 3.1–25.3°
b = 18.1735 (5) ŵ = 0.34 mm1
c = 26.6287 (8) ÅT = 153 K
β = 107.513 (1)°Block, green
V = 7673.2 (4) Å30.16 × 0.12 × 0.11 mm
Z = 4

Data collection

Rigaku R-AXIS SPIDER diffractometer13620 independent reflections
Radiation source: fine-focus sealed tube7422 reflections with I > 2σ(I)
graphiteRint = 0.100
[var phi] and ω scansθmax = 25.3°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −19→19
Tmin = 0.948, Tmax = 0.964k = −21→19
57512 measured reflectionsl = −31→31

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.093H-atom parameters constrained
wR(F2) = 0.290w = 1/[σ2(Fo2) + (0.159P)2] where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
13620 reflectionsΔρmax = 1.47 e Å3
1031 parametersΔρmin = −0.70 e Å3
33 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0065 (7)

Special details

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)

xyzUiso*/UeqOcc. (<1)
Ni10.51131 (4)1.03417 (4)0.30185 (3)0.0332 (3)
O10.6244 (2)1.0747 (2)0.35372 (15)0.0425 (10)
O20.4051 (2)0.9916 (2)0.24517 (16)0.0405 (10)
O30.8696 (4)0.8778 (5)0.5346 (3)0.140 (3)
O40.8102 (3)0.9785 (3)0.4610 (2)0.0640 (14)
O50.8510 (3)0.9599 (4)0.3932 (3)0.109 (3)
O61.1420 (3)0.9104 (3)0.4209 (2)0.0726 (15)
O71.2164 (2)0.8564 (3)0.49189 (19)0.0598 (13)
O81.0962 (4)0.8107 (4)0.6320 (2)0.102 (2)
O90.9629 (4)0.7997 (5)0.6121 (2)0.118 (3)
O101.3372 (3)0.5619 (2)0.62338 (16)0.0508 (11)
O111.2770 (5)0.6866 (4)0.6542 (3)0.127 (3)
O121.2726 (4)0.7690 (4)0.5996 (3)0.102 (2)
O131.0995 (3)0.7107 (3)0.42298 (18)0.0639 (14)
O141.1353 (3)0.6130 (3)0.38853 (19)0.0774 (16)
O151.3402 (4)0.4428 (3)0.5091 (3)0.092 (2)
O170.1841 (3)0.9649 (4)0.2410 (3)0.102 (2)
N10.5890 (3)1.0487 (2)0.25471 (18)0.0349 (11)
N20.7160 (3)1.0756 (3)0.24688 (18)0.0366 (11)
N30.4864 (3)1.0455 (3)0.37249 (18)0.0372 (11)
N40.5239 (3)1.0850 (3)0.45632 (19)0.0392 (12)
N50.4393 (3)1.1266 (2)0.27307 (18)0.0362 (11)
N60.3186 (3)1.1743 (2)0.22166 (18)0.0351 (11)
N70.5244 (3)0.9208 (3)0.31261 (18)0.0382 (11)
N80.4661 (3)0.8095 (2)0.29733 (19)0.0372 (11)
N90.8613 (3)0.9548 (3)0.4406 (3)0.0603 (16)
N101.1504 (3)0.8839 (3)0.4647 (2)0.0493 (14)
N111.0251 (4)0.8202 (4)0.6018 (2)0.0683 (17)
N121.2632 (4)0.7030 (3)0.6109 (2)0.0554 (15)
N131.1364 (3)0.6518 (3)0.4264 (2)0.0558 (15)
N141.3027 (4)0.4623 (3)0.5403 (3)0.0678 (19)
N150.0523 (5)0.9466 (4)0.1851 (3)0.097 (3)
N161.2579 (5)0.3023 (5)0.4119 (3)0.093 (3)
C10.5847 (3)1.0439 (3)0.2013 (2)0.0362 (13)
C20.5181 (4)1.0263 (3)0.1569 (2)0.0437 (15)
H2A0.46361.01520.15930.052*
C30.5351 (4)1.0256 (4)0.1095 (3)0.0530 (17)
H3A0.49061.01450.07850.064*
C40.6155 (4)1.0407 (4)0.1048 (3)0.0606 (19)
H4A0.62401.03930.07110.073*
C50.6816 (4)1.0573 (4)0.1483 (3)0.0535 (17)
H5A0.73641.06700.14570.064*
C60.6648 (3)1.0594 (3)0.1960 (2)0.0401 (14)
C70.6678 (3)1.0671 (3)0.2798 (2)0.0360 (13)
C80.6983 (3)1.0797 (3)0.3371 (2)0.0401 (14)
H8A0.74011.04180.35470.048*
H8B0.72471.12890.34520.048*
C90.6348 (3)1.0839 (3)0.4085 (2)0.0397 (14)
H9A0.65521.13400.42030.048*
H9B0.67511.04740.42970.048*
C100.5476 (3)1.0716 (3)0.4128 (2)0.0390 (14)
C110.4391 (3)1.0654 (3)0.4439 (2)0.0419 (14)
C120.3829 (4)1.0674 (4)0.4726 (3)0.0501 (16)
H12A0.39871.08450.50790.060*
C130.3002 (4)1.0427 (4)0.4465 (3)0.0549 (17)
H13A0.25921.04240.46490.066*
C140.2779 (4)1.0189 (4)0.3948 (3)0.0578 (19)
H14A0.22161.00320.37850.069*
C150.3343 (3)1.0172 (4)0.3661 (3)0.0481 (16)
H15A0.31781.00050.33060.058*
C160.4165 (3)1.0407 (3)0.3909 (2)0.0385 (14)
C170.8062 (3)1.0900 (3)0.2615 (3)0.0434 (15)
H17A0.82151.12410.29190.052*
H17B0.81911.11490.23180.052*
C180.8601 (3)1.0216 (3)0.2758 (2)0.0433 (15)
C190.8303 (4)0.9522 (3)0.2611 (3)0.0555 (19)
H19A0.77260.94530.24190.067*
C200.8834 (4)0.8923 (4)0.2739 (3)0.073 (2)
H20A0.86140.84440.26410.088*
C210.9670 (4)0.9005 (4)0.3004 (3)0.069 (2)
H21A1.00350.85910.30810.083*
C220.9971 (4)0.9694 (4)0.3157 (3)0.064 (2)
H22A1.05470.97580.33510.077*
C230.9447 (4)1.0298 (4)0.3032 (3)0.0531 (17)
H23A0.96691.07750.31340.064*
C240.5730 (4)1.1241 (3)0.5046 (2)0.0438 (15)
H24A0.63401.11900.50900.053*
H24B0.56151.10200.53570.053*
C250.5496 (4)1.2041 (3)0.5010 (2)0.0413 (14)
C260.5860 (4)1.2529 (4)0.4741 (3)0.0548 (17)
H26A0.62821.23620.45940.066*
C270.5603 (4)1.3268 (4)0.4685 (3)0.0613 (19)
H27A0.58461.35990.44960.074*
C280.5001 (4)1.3513 (4)0.4903 (3)0.0496 (16)
H28A0.48191.40110.48560.060*
C290.4662 (4)1.3044 (4)0.5187 (3)0.0474 (15)
H29A0.42661.32230.53500.057*
C300.4894 (4)1.2314 (4)0.5236 (2)0.0476 (15)
H30A0.46431.19900.54260.057*
C310.4383 (3)1.2021 (3)0.2832 (2)0.0339 (13)
C320.4976 (3)1.2463 (3)0.3188 (2)0.0416 (14)
H32A0.54841.22630.34140.050*
C330.4793 (4)1.3192 (3)0.3195 (3)0.0471 (15)
H33A0.51901.35060.34290.057*
C340.4054 (4)1.3494 (3)0.2875 (3)0.0501 (16)
H34A0.39561.40070.28960.060*
C350.3449 (4)1.3062 (3)0.2524 (2)0.0438 (15)
H35A0.29341.32630.23050.053*
C360.3642 (3)1.2319 (3)0.2512 (2)0.0384 (13)
C370.3653 (3)1.1129 (3)0.2362 (2)0.0370 (13)
C380.3391 (3)1.0380 (3)0.2168 (2)0.0373 (13)
H38A0.28551.02450.22350.045*
H38B0.33121.03450.17850.045*
C390.3841 (3)0.9147 (3)0.2455 (3)0.0427 (15)
H39A0.37540.89240.21040.051*
H39B0.33230.90790.25600.051*
C400.4592 (3)0.8812 (3)0.2855 (2)0.0370 (13)
C410.5432 (3)0.8010 (3)0.3368 (2)0.0372 (13)
C420.5834 (4)0.7392 (3)0.3637 (2)0.0436 (15)
H42A0.55910.69150.35690.052*
C430.6609 (4)0.7510 (3)0.4012 (2)0.0464 (15)
H43A0.69050.71040.42080.056*
C440.6961 (4)0.8209 (4)0.4106 (3)0.0492 (16)
H44A0.74910.82690.43670.059*
C450.6564 (3)0.8816 (3)0.3832 (2)0.0425 (15)
H45A0.68140.92910.38950.051*
C460.5778 (3)0.8709 (3)0.3456 (2)0.0372 (13)
C470.2323 (3)1.1776 (4)0.1856 (2)0.0448 (15)
H47A0.22191.13350.16280.054*
H47B0.22701.22140.16270.054*
C480.1668 (3)1.1816 (3)0.2134 (2)0.0364 (13)
C490.0832 (3)1.1935 (3)0.1830 (2)0.0448 (15)
H49A0.06951.19760.14580.054*
C500.0204 (4)1.1995 (4)0.2074 (3)0.0512 (17)
H50A−0.03611.20890.18680.061*
C510.0394 (4)1.1920 (4)0.2611 (3)0.0518 (17)
H51A−0.00381.19630.27750.062*
C520.1227 (4)1.1780 (4)0.2915 (3)0.0543 (17)
H52A0.13621.17300.32870.065*
C530.1853 (3)1.1716 (4)0.2672 (2)0.0473 (16)
H53A0.24131.16020.28770.057*
C540.4008 (3)0.7527 (3)0.2774 (3)0.0433 (15)
H54A0.42650.70330.28540.052*
H54B0.37730.75730.23870.052*
C550.3303 (3)0.7608 (3)0.3024 (2)0.0436 (15)
C560.2494 (4)0.7785 (4)0.2713 (3)0.062 (2)
H56A0.23890.78360.23440.074*
C570.1847 (5)0.7888 (5)0.2919 (4)0.079 (2)
H57A0.12940.79920.26980.094*
C580.2010 (6)0.7840 (5)0.3444 (5)0.096 (3)
H58A0.15670.79300.35930.115*
C590.2789 (6)0.7664 (6)0.3768 (4)0.103 (3)
H59A0.28880.76340.41380.124*
C600.3432 (5)0.7531 (6)0.3552 (3)0.085 (3)
H60A0.39710.73850.37730.102*
C610.9367 (4)0.8862 (4)0.5227 (3)0.0619 (19)
C620.9366 (3)0.9175 (4)0.4735 (3)0.0503 (17)
C631.0040 (4)0.9165 (3)0.4544 (3)0.0488 (16)
H63A0.99990.93750.42100.059*
C641.0792 (3)0.8844 (3)0.4846 (2)0.0429 (15)
C651.0861 (4)0.8549 (3)0.5345 (3)0.0498 (16)
H65A1.13800.83560.55620.060*
C661.0154 (4)0.8550 (4)0.5510 (3)0.0504 (16)
C671.2866 (3)0.5803 (3)0.5798 (2)0.0400 (14)
C681.2462 (3)0.6511 (3)0.5686 (2)0.0379 (13)
C691.1993 (3)0.6749 (3)0.5199 (2)0.0411 (14)
H69A1.17610.72310.51500.049*
C701.1867 (3)0.6272 (3)0.4783 (2)0.0443 (15)
C711.2208 (4)0.5562 (4)0.4845 (3)0.0499 (16)
H71A1.21190.52380.45530.060*
C721.2668 (4)0.5351 (3)0.5333 (3)0.0458 (15)
C730.0782 (11)0.8842 (10)0.1631 (7)0.207 (7)
H73A0.13890.87670.17930.311*
H73B0.06630.89120.12510.311*
H73C0.04760.84090.16960.311*
C74−0.0340 (6)0.9693 (8)0.1677 (5)0.147 (6)
H74A−0.04001.01640.18410.221*
H74B−0.06900.93210.17760.221*
H74C−0.05210.97510.12930.221*
C750.1106 (5)0.9821 (5)0.2220 (4)0.081 (3)
H75A0.09311.02580.23520.097*
C761.2961 (10)0.2397 (9)0.4030 (6)0.194 (6)
H76A1.34010.25210.38690.291*
H76B1.25420.20750.37930.291*
H76C1.32150.21430.43650.291*
C771.2637 (7)0.3659 (8)0.3881 (5)0.146 (6)
H77A1.30350.36050.36770.219*
H77B1.28380.40430.41480.219*
H77C1.20810.37950.36460.219*
O161.3004 (5)0.4249 (3)0.5760 (3)0.115 (3)
O181.1731 (9)0.3887 (8)0.4370 (6)0.234 (6)
C781.1980 (10)0.3238 (8)0.4439 (7)0.184 (7)
H78A1.18160.29060.46670.220*
C800.003 (2)0.9603 (17)0.0144 (13)0.084 (10)*0.25
H80A−0.00171.0092−0.00170.126*0.25
H80B0.06230.94590.02740.126*0.25
H80C−0.02110.96150.04390.126*0.25
C79−0.046 (2)0.9045 (15)−0.0266 (13)0.094 (11)*0.25
H79A−0.10220.9258−0.04270.112*0.25
H79B−0.01740.9040−0.05450.112*0.25
O19−0.0592 (19)0.8280 (16)−0.0159 (13)0.137 (11)*0.25
H19−0.01620.8033−0.01520.206*0.25

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0305 (4)0.0322 (4)0.0385 (4)−0.0002 (3)0.0124 (3)−0.0024 (3)
O10.0281 (18)0.066 (3)0.038 (2)0.0012 (18)0.0160 (17)−0.0047 (19)
O20.0346 (19)0.032 (2)0.053 (3)0.0020 (16)0.0114 (18)0.0064 (18)
O30.102 (5)0.180 (8)0.165 (7)0.053 (5)0.083 (5)0.081 (6)
O40.041 (2)0.072 (4)0.079 (4)0.012 (2)0.017 (2)−0.012 (3)
O50.073 (4)0.187 (7)0.081 (4)0.063 (4)0.042 (3)0.072 (5)
O60.053 (3)0.099 (4)0.074 (4)0.013 (3)0.032 (3)0.026 (3)
O70.037 (2)0.074 (3)0.068 (3)0.013 (2)0.016 (2)0.006 (2)
O80.090 (4)0.118 (5)0.078 (4)−0.002 (4)−0.007 (3)0.031 (4)
O90.090 (4)0.205 (8)0.072 (4)0.002 (5)0.042 (4)0.045 (5)
O100.058 (3)0.046 (3)0.045 (3)0.009 (2)0.011 (2)0.009 (2)
O110.212 (8)0.094 (5)0.067 (4)0.071 (5)0.029 (5)−0.006 (4)
O120.130 (5)0.079 (5)0.119 (5)−0.029 (4)0.071 (4)−0.040 (4)
O130.065 (3)0.062 (3)0.057 (3)0.018 (2)0.007 (2)0.005 (2)
O140.086 (4)0.084 (4)0.049 (3)0.020 (3)0.000 (3)−0.012 (3)
O150.089 (4)0.079 (4)0.098 (5)0.035 (3)0.012 (4)−0.025 (3)
O170.058 (3)0.105 (5)0.149 (6)0.005 (3)0.039 (4)0.018 (4)
N10.033 (2)0.033 (3)0.036 (3)−0.0005 (18)0.008 (2)−0.003 (2)
N20.031 (2)0.041 (3)0.041 (3)0.0010 (19)0.015 (2)0.002 (2)
N30.035 (2)0.039 (3)0.037 (3)0.0016 (19)0.009 (2)−0.007 (2)
N40.035 (2)0.047 (3)0.040 (3)0.004 (2)0.019 (2)−0.006 (2)
N50.038 (2)0.033 (3)0.038 (3)−0.0039 (19)0.012 (2)−0.005 (2)
N60.033 (2)0.031 (3)0.042 (3)0.0044 (19)0.011 (2)0.002 (2)
N70.034 (2)0.040 (3)0.040 (3)0.005 (2)0.011 (2)0.003 (2)
N80.042 (3)0.029 (3)0.044 (3)−0.0049 (19)0.018 (2)−0.002 (2)
N90.045 (3)0.062 (4)0.081 (5)0.008 (3)0.029 (3)0.012 (3)
N100.034 (3)0.056 (4)0.058 (4)0.006 (2)0.015 (3)0.004 (3)
N110.068 (4)0.090 (5)0.046 (4)−0.002 (3)0.017 (3)0.007 (3)
N120.081 (4)0.036 (3)0.045 (3)0.018 (3)0.012 (3)0.005 (3)
N130.057 (3)0.062 (4)0.043 (3)0.009 (3)0.007 (3)−0.006 (3)
N140.077 (4)0.043 (4)0.070 (4)0.019 (3)0.003 (4)−0.009 (3)
N150.087 (5)0.074 (5)0.112 (6)0.016 (4)0.004 (5)−0.005 (5)
N160.093 (5)0.086 (6)0.075 (5)−0.003 (4)−0.011 (4)−0.019 (4)
C10.040 (3)0.031 (3)0.036 (3)0.003 (2)0.010 (3)0.002 (2)
C20.045 (3)0.034 (3)0.054 (4)−0.003 (2)0.017 (3)−0.003 (3)
C30.047 (4)0.071 (5)0.040 (4)0.009 (3)0.013 (3)0.003 (3)
C40.059 (4)0.085 (6)0.041 (4)0.000 (4)0.019 (3)0.007 (3)
C50.051 (4)0.066 (5)0.052 (4)−0.001 (3)0.027 (3)0.009 (3)
C60.042 (3)0.040 (3)0.040 (3)0.009 (3)0.016 (3)0.008 (3)
C70.039 (3)0.030 (3)0.041 (3)0.000 (2)0.014 (3)−0.001 (2)
C80.034 (3)0.050 (4)0.039 (3)−0.001 (2)0.014 (3)−0.005 (3)
C90.029 (3)0.050 (4)0.040 (3)0.003 (2)0.010 (2)−0.012 (3)
C100.036 (3)0.040 (4)0.042 (3)0.004 (2)0.014 (3)−0.001 (3)
C110.038 (3)0.043 (4)0.046 (4)0.005 (3)0.015 (3)0.003 (3)
C120.051 (4)0.061 (4)0.047 (4)0.002 (3)0.027 (3)−0.002 (3)
C130.045 (3)0.071 (5)0.056 (4)0.002 (3)0.027 (3)0.005 (3)
C140.042 (3)0.072 (5)0.065 (5)−0.014 (3)0.024 (3)0.002 (4)
C150.039 (3)0.052 (4)0.052 (4)−0.002 (3)0.012 (3)−0.001 (3)
C160.033 (3)0.037 (3)0.049 (4)−0.001 (2)0.018 (3)0.002 (3)
C170.030 (3)0.045 (4)0.059 (4)−0.005 (2)0.019 (3)0.003 (3)
C180.033 (3)0.049 (4)0.053 (4)0.003 (2)0.020 (3)0.008 (3)
C190.044 (3)0.038 (4)0.082 (5)−0.003 (3)0.015 (3)0.004 (3)
C200.061 (4)0.043 (4)0.111 (7)0.010 (3)0.020 (4)0.010 (4)
C210.042 (4)0.066 (5)0.100 (6)0.016 (3)0.022 (4)0.015 (4)
C220.037 (3)0.075 (6)0.078 (5)0.008 (3)0.015 (3)0.024 (4)
C230.042 (3)0.056 (4)0.066 (5)−0.008 (3)0.023 (3)0.005 (3)
C240.043 (3)0.054 (4)0.034 (3)0.004 (3)0.012 (3)−0.008 (3)
C250.046 (3)0.039 (3)0.041 (3)−0.001 (3)0.015 (3)−0.008 (3)
C260.057 (4)0.055 (5)0.064 (5)−0.002 (3)0.035 (3)−0.012 (3)
C270.073 (4)0.045 (4)0.077 (5)−0.016 (3)0.039 (4)−0.011 (4)
C280.055 (4)0.047 (4)0.052 (4)0.002 (3)0.023 (3)−0.006 (3)
C290.047 (3)0.048 (4)0.054 (4)0.006 (3)0.027 (3)−0.001 (3)
C300.048 (3)0.054 (4)0.050 (4)0.002 (3)0.028 (3)0.000 (3)
C310.032 (3)0.027 (3)0.046 (3)0.003 (2)0.017 (2)0.001 (2)
C320.039 (3)0.044 (4)0.045 (3)−0.008 (3)0.018 (3)−0.001 (3)
C330.052 (3)0.039 (4)0.053 (4)−0.007 (3)0.020 (3)−0.004 (3)
C340.062 (4)0.028 (3)0.063 (4)−0.003 (3)0.023 (3)0.000 (3)
C350.053 (3)0.030 (3)0.051 (4)0.007 (3)0.020 (3)0.004 (3)
C360.044 (3)0.033 (3)0.043 (3)0.004 (2)0.019 (3)0.004 (3)
C370.038 (3)0.041 (3)0.032 (3)−0.002 (2)0.011 (2)0.000 (2)
C380.032 (3)0.032 (3)0.048 (3)0.004 (2)0.012 (2)0.003 (3)
C390.042 (3)0.024 (3)0.058 (4)−0.004 (2)0.010 (3)−0.007 (3)
C400.040 (3)0.032 (3)0.042 (3)−0.001 (2)0.017 (3)−0.004 (2)
C410.040 (3)0.031 (3)0.046 (3)0.004 (2)0.021 (3)−0.003 (2)
C420.055 (3)0.029 (3)0.057 (4)0.000 (3)0.032 (3)0.004 (3)
C430.046 (3)0.046 (4)0.052 (4)0.010 (3)0.021 (3)0.011 (3)
C440.040 (3)0.053 (4)0.051 (4)−0.001 (3)0.010 (3)0.004 (3)
C450.035 (3)0.034 (3)0.057 (4)−0.002 (2)0.011 (3)0.002 (3)
C460.041 (3)0.028 (3)0.049 (4)−0.002 (2)0.022 (3)−0.001 (2)
C470.032 (3)0.051 (4)0.050 (4)0.004 (3)0.011 (3)0.002 (3)
C480.031 (3)0.034 (3)0.047 (4)−0.002 (2)0.016 (3)0.000 (3)
C490.036 (3)0.052 (4)0.043 (3)0.001 (3)0.007 (3)−0.004 (3)
C500.038 (3)0.064 (5)0.049 (4)0.000 (3)0.008 (3)−0.002 (3)
C510.037 (3)0.058 (4)0.065 (5)−0.001 (3)0.022 (3)−0.003 (3)
C520.049 (4)0.072 (5)0.044 (4)0.001 (3)0.017 (3)0.003 (3)
C530.032 (3)0.060 (4)0.050 (4)0.004 (3)0.013 (3)0.011 (3)
C540.041 (3)0.034 (3)0.056 (4)−0.009 (2)0.016 (3)−0.005 (3)
C550.038 (3)0.041 (4)0.055 (4)−0.010 (3)0.019 (3)−0.004 (3)
C560.049 (4)0.070 (5)0.069 (5)−0.003 (3)0.020 (4)0.016 (4)
C570.056 (4)0.087 (7)0.105 (7)0.004 (4)0.042 (5)0.010 (5)
C580.072 (6)0.103 (8)0.135 (9)−0.031 (5)0.065 (6)−0.048 (7)
C590.092 (6)0.155 (8)0.073 (5)−0.040 (5)0.041 (5)−0.026 (5)
C600.051 (4)0.162 (9)0.035 (4)−0.023 (5)0.001 (3)−0.002 (5)
C610.051 (4)0.082 (6)0.065 (5)0.018 (3)0.037 (4)0.015 (4)
C620.036 (3)0.051 (4)0.068 (5)0.009 (3)0.022 (3)0.012 (3)
C630.044 (3)0.046 (4)0.058 (4)0.009 (3)0.018 (3)0.009 (3)
C640.035 (3)0.046 (4)0.051 (4)0.005 (3)0.017 (3)0.003 (3)
C650.045 (3)0.047 (4)0.058 (4)0.009 (3)0.017 (3)0.000 (3)
C660.046 (3)0.059 (4)0.052 (4)0.007 (3)0.023 (3)0.008 (3)
C670.037 (3)0.037 (3)0.046 (4)0.005 (2)0.013 (3)0.011 (3)
C680.043 (3)0.033 (3)0.037 (3)0.000 (2)0.010 (3)−0.002 (2)
C690.046 (3)0.039 (3)0.034 (3)0.008 (3)0.006 (3)0.005 (3)
C700.040 (3)0.051 (4)0.035 (3)0.003 (3)0.001 (3)0.004 (3)
C710.051 (4)0.048 (4)0.047 (4)0.004 (3)0.010 (3)−0.009 (3)
C720.050 (3)0.031 (3)0.054 (4)0.004 (3)0.013 (3)−0.007 (3)
C730.221 (10)0.175 (10)0.192 (10)0.039 (8)0.010 (8)−0.020 (8)
C740.079 (7)0.186 (14)0.148 (12)0.016 (7)−0.009 (7)0.053 (9)
C750.066 (5)0.073 (6)0.117 (8)−0.003 (4)0.047 (5)0.006 (5)
C760.191 (9)0.159 (9)0.179 (9)0.037 (8)−0.025 (7)−0.020 (8)
C770.127 (9)0.147 (12)0.123 (10)−0.058 (8)−0.024 (8)0.053 (9)
O160.191 (7)0.041 (4)0.102 (5)0.029 (4)0.028 (5)0.016 (3)
O180.244 (9)0.175 (8)0.243 (9)0.043 (7)0.012 (7)−0.047 (7)
C780.166 (9)0.200 (10)0.181 (10)−0.067 (8)0.046 (8)0.003 (8)

Geometric parameters (Å, °)

Ni1—N32.055 (5)C26—C271.403 (9)
Ni1—N52.070 (5)C26—H26A0.9500
Ni1—N12.072 (5)C27—C281.374 (9)
Ni1—N72.082 (5)C27—H27A0.9500
Ni1—O22.096 (4)C28—C291.366 (9)
Ni1—O12.103 (4)C28—H28A0.9500
O1—C91.425 (7)C29—C301.378 (9)
O1—C81.429 (7)C29—H29A0.9500
O2—C381.410 (6)C30—H30A0.9500
O2—C391.440 (6)C31—C361.381 (7)
O3—C611.257 (9)C31—C321.396 (7)
O4—N91.215 (7)C32—C331.361 (8)
O5—N91.225 (8)C32—H32A0.9500
O6—N101.232 (7)C33—C341.381 (8)
O7—N101.224 (6)C33—H33A0.9500
O8—N111.225 (7)C34—C351.392 (8)
O9—N111.207 (8)C34—H34A0.9500
O10—C671.257 (6)C35—C361.392 (8)
O11—N121.146 (8)C35—H35A0.9500
O12—N121.259 (8)C37—C381.475 (8)
O13—N131.224 (7)C38—H38A0.9900
O14—N131.226 (7)C38—H38B0.9900
O15—N141.231 (9)C39—C401.504 (8)
O17—C751.214 (9)C39—H39A0.9900
N1—C71.322 (6)C39—H39B0.9900
N1—C11.405 (7)C41—C461.384 (8)
N2—C71.362 (7)C41—C421.392 (8)
N2—C61.397 (7)C42—C431.389 (8)
N2—C171.455 (6)C42—H42A0.9500
N3—C101.325 (7)C43—C441.390 (9)
N3—C161.393 (7)C43—H43A0.9500
N4—C101.354 (8)C44—C451.379 (8)
N4—C111.394 (7)C44—H44A0.9500
N4—C241.481 (7)C45—C461.400 (7)
N5—C371.347 (6)C45—H45A0.9500
N5—C311.400 (7)C47—C481.491 (8)
N6—C371.348 (7)C47—H47A0.9900
N6—C361.389 (7)C47—H47B0.9900
N6—C471.468 (6)C48—C531.385 (8)
N7—C401.320 (7)C48—C491.398 (7)
N7—C461.384 (7)C49—C501.390 (9)
N8—C401.339 (7)C49—H49A0.9500
N8—C411.399 (7)C50—C511.377 (9)
N8—C541.475 (7)C50—H50A0.9500
N9—C621.461 (8)C51—C521.400 (8)
N10—C641.434 (8)C51—H51A0.9500
N11—C661.457 (9)C52—C531.386 (9)
N12—C681.429 (8)C52—H52A0.9500
N13—C701.454 (7)C53—H53A0.9500
N14—O161.178 (9)C54—C551.520 (8)
N14—C721.442 (8)C54—H54A0.9900
N15—C751.321 (11)C54—H54B0.9900
N15—C731.403 (17)C55—C601.364 (9)
N15—C741.430 (11)C55—C561.389 (8)
N16—C771.334 (12)C56—C571.358 (11)
N16—C761.357 (15)C56—H56A0.9500
N16—C781.545 (19)C57—C581.344 (13)
C1—C21.392 (8)C57—H57A0.9500
C1—C61.409 (8)C58—C591.360 (13)
C2—C31.375 (9)C58—H58A0.9500
C2—H2A0.9500C59—C601.380 (12)
C3—C41.406 (9)C59—H59A0.9500
C3—H3A0.9500C60—H60A0.9500
C4—C51.369 (9)C61—C661.417 (9)
C4—H4A0.9500C61—C621.427 (9)
C5—C61.382 (9)C62—C631.364 (9)
C5—H5A0.9500C63—C641.394 (8)
C7—C81.476 (8)C63—H63A0.9500
C8—H8A0.9900C64—C651.406 (9)
C8—H8B0.9900C65—C661.373 (9)
C9—C101.505 (8)C65—H65A0.9500
C9—H9A0.9900C67—C721.439 (8)
C9—H9B0.9900C67—C681.440 (8)
C11—C121.373 (9)C68—C691.368 (7)
C11—C161.421 (8)C69—C701.372 (8)
C12—C131.415 (9)C69—H69A0.9500
C12—H12A0.9500C70—C711.399 (8)
C13—C141.383 (10)C71—C721.351 (9)
C13—H13A0.9500C71—H71A0.9500
C14—C151.378 (9)C73—H73A0.9800
C14—H14A0.9500C73—H73B0.9800
C15—C161.393 (8)C73—H73C0.9800
C15—H15A0.9500C74—H74A0.9800
C17—C181.513 (8)C74—H74B0.9800
C17—H17A0.9900C74—H74C0.9800
C17—H17B0.9900C75—H75A0.9500
C18—C191.368 (8)C76—H76A0.9800
C18—C231.384 (8)C76—H76B0.9800
C19—C201.379 (9)C76—H76C0.9800
C19—H19A0.9500C77—H77A0.9800
C20—C211.364 (9)C77—H77B0.9800
C20—H20A0.9500C77—H77C0.9800
C21—C221.364 (10)O18—C781.245 (3)
C21—H21A0.9500C78—H78A0.9500
C22—C231.378 (9)C80—C791.530 (3)
C22—H22A0.9500C80—H80A0.9800
C23—H23A0.9500C80—H80B0.9800
C24—C251.500 (8)C80—H80C0.9800
C24—H24A0.9900C79—O191.450 (3)
C24—H24B0.9900C79—H79A0.9900
C25—C261.388 (9)C79—H79B0.9900
C25—C301.403 (8)O19—H190.8400
N3—Ni1—N590.26 (18)C31—C32—H32A121.5
N3—Ni1—N1151.23 (17)C32—C33—C34122.6 (6)
N5—Ni1—N193.95 (18)C32—C33—H33A118.7
N3—Ni1—N790.82 (19)C34—C33—H33A118.7
N5—Ni1—N7151.40 (16)C33—C34—C35121.3 (6)
N1—Ni1—N798.69 (18)C33—C34—H34A119.3
N3—Ni1—O2109.74 (17)C35—C34—H34A119.3
N5—Ni1—O276.42 (15)C34—C35—C36115.9 (5)
N1—Ni1—O298.90 (17)C34—C35—H35A122.0
N7—Ni1—O276.34 (15)C36—C35—H35A122.0
N3—Ni1—O175.55 (16)C31—C36—N6106.7 (5)
N5—Ni1—O1105.16 (16)C31—C36—C35122.4 (5)
N1—Ni1—O175.88 (16)N6—C36—C35130.8 (5)
N7—Ni1—O1102.77 (16)N5—C37—N6112.2 (5)
O2—Ni1—O1174.58 (16)N5—C37—C38122.3 (5)
C9—O1—C8117.2 (4)N6—C37—C38125.4 (4)
C9—O1—Ni1121.5 (3)O2—C38—C37105.3 (4)
C8—O1—Ni1120.1 (3)O2—C38—H38A110.7
C38—O2—C39115.6 (4)C37—C38—H38A110.7
C38—O2—Ni1121.1 (3)O2—C38—H38B110.7
C39—O2—Ni1120.5 (3)C37—C38—H38B110.7
C7—N1—C1105.5 (5)H38A—C38—H38B108.8
C7—N1—Ni1115.5 (4)O2—C39—C40104.2 (4)
C1—N1—Ni1138.9 (3)O2—C39—H39A110.9
C7—N2—C6107.1 (4)C40—C39—H39A110.9
C7—N2—C17127.3 (5)O2—C39—H39B110.9
C6—N2—C17125.2 (5)C40—C39—H39B110.9
C10—N3—C16104.8 (5)H39A—C39—H39B108.9
C10—N3—Ni1117.4 (4)N7—C40—N8113.8 (5)
C16—N3—Ni1137.3 (4)N7—C40—C39122.5 (5)
C10—N4—C11106.6 (5)N8—C40—C39123.7 (5)
C10—N4—C24127.1 (5)C46—C41—C42122.9 (5)
C11—N4—C24125.6 (5)C46—C41—N8105.5 (5)
C37—N5—C31105.0 (4)C42—C41—N8131.6 (5)
C37—N5—Ni1114.9 (4)C43—C42—C41116.3 (5)
C31—N5—Ni1139.7 (3)C43—C42—H42A121.8
C37—N6—C36106.9 (4)C41—C42—H42A121.8
C37—N6—C47126.0 (5)C42—C43—C44121.4 (6)
C36—N6—C47126.8 (4)C42—C43—H43A119.3
C40—N7—C46104.7 (5)C44—C43—H43A119.3
C40—N7—Ni1115.4 (3)C45—C44—C43121.9 (5)
C46—N7—Ni1139.2 (4)C45—C44—H44A119.1
C40—N8—C41106.1 (4)C43—C44—H44A119.1
C40—N8—C54126.4 (4)C44—C45—C46117.6 (5)
C41—N8—C54127.0 (5)C44—C45—H45A121.2
O4—N9—O5122.2 (6)C46—C45—H45A121.2
O4—N9—C62119.0 (7)N7—C46—C41109.8 (5)
O5—N9—C62118.8 (6)N7—C46—C45130.2 (5)
O7—N10—O6123.0 (6)C41—C46—C45120.0 (5)
O7—N10—C64118.6 (6)N6—C47—C48113.2 (5)
O6—N10—C64118.4 (5)N6—C47—H47A108.9
O9—N11—O8122.1 (7)C48—C47—H47A108.9
O9—N11—C66118.8 (6)N6—C47—H47B108.9
O8—N11—C66119.0 (7)C48—C47—H47B108.9
O11—N12—O12119.1 (7)H47A—C47—H47B107.8
O11—N12—C68123.6 (6)C53—C48—C49119.4 (5)
O12—N12—C68116.7 (6)C53—C48—C47122.7 (5)
O13—N13—O14123.9 (6)C49—C48—C47117.9 (5)
O13—N13—C70118.2 (5)C50—C49—C48119.9 (6)
O14—N13—C70117.9 (6)C50—C49—H49A120.1
O16—N14—O15121.7 (7)C48—C49—H49A120.1
O16—N14—C72121.4 (8)C51—C50—C49120.5 (6)
O15—N14—C72116.8 (7)C51—C50—H50A119.8
C75—N15—C73117.1 (9)C49—C50—H50A119.8
C75—N15—C74122.8 (9)C50—C51—C52119.8 (6)
C73—N15—C74120.1 (11)C50—C51—H51A120.1
C77—N16—C76122.7 (14)C52—C51—H51A120.1
C77—N16—C78101.1 (11)C53—C52—C51119.7 (6)
C76—N16—C78136.1 (12)C53—C52—H52A120.2
C2—C1—N1131.3 (5)C51—C52—H52A120.2
C2—C1—C6119.7 (6)C48—C53—C52120.6 (5)
N1—C1—C6109.1 (5)C48—C53—H53A119.7
C3—C2—C1116.8 (6)C52—C53—H53A119.7
C3—C2—H2A121.6N8—C54—C55110.9 (5)
C1—C2—H2A121.6N8—C54—H54A109.5
C2—C3—C4122.9 (6)C55—C54—H54A109.5
C2—C3—H3A118.5N8—C54—H54B109.5
C4—C3—H3A118.5C55—C54—H54B109.5
C5—C4—C3120.7 (7)H54A—C54—H54B108.1
C5—C4—H4A119.6C60—C55—C56117.5 (7)
C3—C4—H4A119.6C60—C55—C54122.6 (6)
C4—C5—C6116.7 (6)C56—C55—C54119.9 (6)
C4—C5—H5A121.6C57—C56—C55122.3 (8)
C6—C5—H5A121.6C57—C56—H56A118.9
C5—C6—N2131.6 (6)C55—C56—H56A118.9
C5—C6—C1123.1 (5)C58—C57—C56118.3 (8)
N2—C6—C1105.3 (5)C58—C57—H57A120.8
N1—C7—N2112.9 (5)C56—C57—H57A120.8
N1—C7—C8122.8 (5)C57—C58—C59122.1 (9)
N2—C7—C8124.3 (5)C57—C58—H58A119.0
O1—C8—C7104.5 (4)C59—C58—H58A119.0
O1—C8—H8A110.9C58—C59—C60119.1 (9)
C7—C8—H8A110.9C58—C59—H59A120.5
O1—C8—H8B110.9C60—C59—H59A120.5
C7—C8—H8B110.9C55—C60—C59120.7 (7)
H8A—C8—H8B108.9C55—C60—H60A119.7
O1—C9—C10103.7 (4)C59—C60—H60A119.7
O1—C9—H9A111.0O3—C61—C66124.4 (7)
C10—C9—H9A111.0O3—C61—C62121.6 (7)
O1—C9—H9B111.0C66—C61—C62113.2 (6)
C10—C9—H9B111.0C63—C62—C61124.2 (6)
H9A—C9—H9B109.0C63—C62—N9115.8 (6)
N3—C10—N4114.0 (5)C61—C62—N9120.0 (6)
N3—C10—C9120.9 (5)C62—C63—C64119.1 (6)
N4—C10—C9125.1 (5)C62—C63—H63A120.5
C12—C11—N4132.1 (6)C64—C63—H63A120.5
C12—C11—C16122.7 (5)C63—C64—C65120.6 (6)
N4—C11—C16105.2 (5)C63—C64—N10119.2 (6)
C11—C12—C13116.3 (6)C65—C64—N10120.2 (5)
C11—C12—H12A121.9C66—C65—C64117.9 (6)
C13—C12—H12A121.9C66—C65—H65A121.0
C14—C13—C12121.1 (6)C64—C65—H65A121.0
C14—C13—H13A119.4C65—C66—C61124.9 (6)
C12—C13—H13A119.4C65—C66—N11115.4 (6)
C15—C14—C13122.5 (6)C61—C66—N11119.6 (6)
C15—C14—H14A118.8O10—C67—C72124.0 (5)
C13—C14—H14A118.8O10—C67—C68124.7 (6)
C14—C15—C16117.6 (6)C72—C67—C68111.1 (5)
C14—C15—H15A121.2C69—C68—N12117.4 (5)
C16—C15—H15A121.2C69—C68—C67125.2 (5)
N3—C16—C15130.9 (6)N12—C68—C67117.2 (5)
N3—C16—C11109.3 (5)C68—C69—C70118.1 (5)
C15—C16—C11119.8 (6)C68—C69—H69A121.0
N2—C17—C18113.8 (5)C70—C69—H69A121.0
N2—C17—H17A108.8C69—C70—C71122.0 (5)
C18—C17—H17A108.8C69—C70—N13118.5 (5)
N2—C17—H17B108.8C71—C70—N13119.5 (6)
C18—C17—H17B108.8C72—C71—C70117.8 (6)
H17A—C17—H17B107.7C72—C71—H71A121.1
C19—C18—C23118.2 (6)C70—C71—H71A121.1
C19—C18—C17123.3 (5)C71—C72—C67125.7 (6)
C23—C18—C17118.4 (5)C71—C72—N14118.5 (6)
C18—C19—C20120.5 (6)C67—C72—N14115.8 (5)
C18—C19—H19A119.8N15—C73—H73A109.5
C20—C19—H19A119.8N15—C73—H73B109.5
C21—C20—C19121.3 (7)H73A—C73—H73B109.5
C21—C20—H20A119.4N15—C73—H73C109.5
C19—C20—H20A119.4H73A—C73—H73C109.5
C20—C21—C22118.6 (7)H73B—C73—H73C109.5
C20—C21—H21A120.7N15—C74—H74A109.5
C22—C21—H21A120.7N15—C74—H74B109.5
C21—C22—C23120.7 (6)H74A—C74—H74B109.5
C21—C22—H22A119.6N15—C74—H74C109.5
C23—C22—H22A119.6H74A—C74—H74C109.5
C22—C23—C18120.6 (6)H74B—C74—H74C109.5
C22—C23—H23A119.7O17—C75—N15127.2 (9)
C18—C23—H23A119.7O17—C75—H75A116.4
N4—C24—C25110.3 (4)N15—C75—H75A116.4
N4—C24—H24A109.6N16—C76—H76A109.5
C25—C24—H24A109.6N16—C76—H76B109.5
N4—C24—H24B109.6H76A—C76—H76B109.5
C25—C24—H24B109.6N16—C76—H76C109.5
H24A—C24—H24B108.1H76A—C76—H76C109.5
C26—C25—C30118.3 (6)H76B—C76—H76C109.5
C26—C25—C24120.4 (6)N16—C77—H77A109.5
C30—C25—C24121.3 (6)N16—C77—H77B109.5
C25—C26—C27120.0 (6)H77A—C77—H77B109.5
C25—C26—H26A120.0N16—C77—H77C109.5
C27—C26—H26A120.0H77A—C77—H77C109.5
C28—C27—C26120.2 (7)H77B—C77—H77C109.5
C28—C27—H27A119.9O18—C78—N16113.5 (16)
C26—C27—H27A119.9O18—C78—H78A123.2
C29—C28—C27120.3 (6)N16—C78—H78A123.2
C29—C28—H28A119.9C79—C80—H80A109.5
C27—C28—H28A119.9C79—C80—H80B109.5
C28—C29—C30120.2 (6)H80A—C80—H80B109.5
C28—C29—H29A119.9C79—C80—H80C109.5
C30—C29—H29A119.9H80A—C80—H80C109.5
C29—C30—C25121.0 (6)H80B—C80—H80C109.5
C29—C30—H30A119.5O19—C79—C80125 (3)
C25—C30—H30A119.5O19—C79—H79A106.1
C36—C31—C32120.6 (5)C80—C79—H79A106.1
C36—C31—N5109.0 (5)O19—C79—H79B106.1
C32—C31—N5130.3 (5)C80—C79—H79B106.1
C33—C32—C31117.0 (5)H79A—C79—H79B106.3
C33—C32—H32A121.5C79—O19—H19109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2A···O10i0.952.473.286 (8)144
C8—H8A···O50.992.353.337 (9)173
C8—H8B···O12ii0.992.363.185 (9)140
C9—H9A···O12ii0.992.283.125 (9)142
C9—H9B···O40.992.493.417 (7)156
C17—H17A···O8ii0.992.393.341 (9)161
C38—H38A···O170.992.173.134 (8)164
C38—H38B···O10i0.992.313.072 (7)133
C39—H39A···O10i0.992.363.137 (9)135
C39—H39A···O11i0.992.353.141 (10)137
C43—H43A···O16iii0.952.463.281 (8)144
C56—H56A···O11i0.952.463.346 (11)155
C65—H65A···O120.952.503.438 (10)169
C77—H77B···O150.982.503.389 (15)150

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) −x+2, −y+2, −z+1; (iii) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2826).

References

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