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Acta Cryst. (2009). E65, m274    [ doi:10.1107/S1600536809004437 ]

Bis(perchlorato-[kappa]O)tetrakis[1-(2-pyridyl)-4-(4-pyridylmethyl-[kappa]N)piperazine]cadmium(II)

G. A. Farnum and R. L. LaDuca

Abstract top

In the title compound, [Cd(ClO4)2(C15H18N4)4], the CdII ion is coordinated in a slightly distorted octahedral environment by two trans monodentate perchlorate ligands and four 1-(2-pyridyl)-4-(4-pyridylmethyl)piperazine (pmpp) ligands. In the crystal structure, molecules are organized into layers parallel to the ab plane by C-H...O interactions. Similar interactions promote the stacking of these layers into the three-dimensional crystal structure.

Comment top

In an attempt to prepare a cadmium perchlorate coordination polymer containing pmpp (Farnum et al., 2009), colourless blocks of the title compound were obtained. The asymmetric unit contains a single molecule, [Cd(pmpp)4(ClO4)2], wherein an octahedrally coordinated CdII ion is bound by two trans monodentate perchlorato ligands and four pmpp ligands, bound via N atoms within their 4-pyridyl termini (Fig. 1). The title compound crystallizes in the noncentrosymmetric monoclinic space group Cc without appreciable racemic twinning, as evidenced by a Flack parameter (Flack, 1983) of -0.043 (13).

Individual [Cd(pmpp)4(ClO4)2] molecules aggregate through C—H···O interactions, constructing pseudo layers coincident with the ab crystal planes (Fig. 2). In turn these layers stack in an AB pattern along the c crystal direction by a different C—H···O pathway (Fig. 3).

Related literature top

For a silver nitrate supramolecular complex and the synthesis of pmpp, see: Farnum et al. (2009).

Experimental top

All chemicals were obtained commercially. Cadmium perchlorate hexahydrate (20 mg, 0.064 mmol) was dissolved in 1.5 ml water in a glass vial at 298 K. A 0.75 ml aliquot of a 1:1 water–ethanol mixture was carefully layered onto the aqueous solution, followed by 1.5 ml of an ethanolic solution of pmpp (32.5 mg, 0.128 mmol). Colourless blocks of the title compound formed after 2 weeks.

Refinement top

All H atoms bound to C atoms were placed in calculated positions, with C—H = 0.95 Å or 0.99 Å, and refined in riding mode with Uiso = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Color codes: violet Cd, green Cl, light blue N, red O, black C. H-atom positions are shown as grey sticks.
[Figure 2] Fig. 2. A supramolecular layer formed by C—H···O interactions between molecules of the title compound.
[Figure 3] Fig. 3. Part of the crystal structure showing the AB stacking pattern of supramolecular layers.
Bis(perchlorato-κO)tetrakis[1-(2-pyridyl)-4-(4-pyridylmethyl- κN)piperazine]cadmium(II) top
Crystal data top
[Cd(ClO4)2(C15H18N4)4]F(000) = 2760
Mr = 1328.64Dx = 1.424 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C-2ycCell parameters from 34115 reflections
a = 34.958 (4) Åθ = 1.5–28.3°
b = 9.1736 (11) ŵ = 0.51 mm−1
c = 24.153 (3) ÅT = 173 K
β = 126.874 (1)°Block, colourless
V = 6196.4 (13) Å30.20 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker SMART 1K
diffractometer		13967 independent reflections
Radiation source: fine-focus sealed tube11273 reflections with I > 2σ(I)
graphiteRint = 0.052
ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		h = −44→44
Tmin = 0.875, Tmax = 0.941k = −12→12
34115 measured reflectionsl = −30→30
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0388P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
13967 reflectionsΔρmax = 0.70 e Å−3
784 parametersΔρmin = −0.41 e Å−3
2 restraintsAbsolute structure: Flack (1983), with 6755 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.041 (13)
Crystal data top
[Cd(ClO4)2(C15H18N4)4]V = 6196.4 (13) Å3
Mr = 1328.64Z = 4
Monoclinic, CcMo Kα radiation
a = 34.958 (4) ŵ = 0.51 mm−1
b = 9.1736 (11) ÅT = 173 K
c = 24.153 (3) Å0.20 × 0.16 × 0.12 mm
β = 126.874 (1)°
Data collection top
Bruker SMART 1K
diffractometer		13967 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		11273 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.941Rint = 0.052
34115 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.084Δρmax = 0.70 e Å−3
S = 0.98Δρmin = −0.41 e Å−3
13967 reflectionsAbsolute structure: Flack (1983), with 6755 Friedel pairs
784 parametersFlack parameter: −0.041 (13)
2 restraints
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*/Ueq
Cd10.944502 (8)0.40038 (2)0.851212 (10)0.02197 (6)
Cl20.89524 (3)0.08947 (10)0.73405 (4)0.0314 (2)
Cl30.98569 (3)0.74096 (9)0.95355 (4)0.0313 (2)
O10.85179 (12)0.0194 (5)0.70850 (18)0.0832 (13)
O20.93073 (14)−0.0123 (5)0.7526 (2)0.1008 (15)
O30.91053 (10)0.1719 (3)0.79483 (15)0.0531 (8)
O40.88951 (14)0.1820 (5)0.68378 (18)0.1070 (17)
O50.98435 (12)0.5974 (3)0.93104 (17)0.0626 (9)
O60.97222 (13)0.7354 (4)0.99851 (18)0.0806 (12)
O71.03264 (12)0.7964 (4)0.99005 (18)0.0760 (11)
O80.95294 (14)0.8286 (4)0.89449 (17)0.0869 (13)
N11.01789 (10)0.2833 (3)0.90920 (15)0.0264 (7)
N21.19180 (9)0.1926 (3)1.00871 (14)0.0238 (6)
N31.26147 (11)0.2236 (4)0.98396 (16)0.0420 (9)
N41.27668 (11)0.2627 (4)0.90449 (17)0.0383 (8)
N50.96399 (10)0.5031 (3)0.78326 (15)0.0291 (7)
N61.04588 (10)0.5644 (3)0.66929 (15)0.0271 (7)
N71.13255 (12)0.5004 (6)0.68796 (18)0.0714 (14)
N81.17255 (12)0.5530 (3)0.64101 (17)0.0386 (8)
N90.92928 (10)0.3042 (3)0.92556 (14)0.0250 (6)
N100.83893 (10)0.2041 (3)1.02504 (14)0.0273 (7)
N110.74481 (11)0.2154 (4)0.98869 (15)0.0398 (8)
N120.69473 (11)0.1813 (3)1.02141 (15)0.0331 (7)
N130.86879 (10)0.5004 (3)0.78932 (14)0.0244 (6)
N140.69229 (9)0.5659 (3)0.68151 (14)0.0230 (6)
N150.61776 (11)0.4882 (5)0.69084 (16)0.0579 (11)
N160.59698 (12)0.5186 (4)0.76485 (17)0.0407 (8)
C11.02538 (12)0.1405 (4)0.91269 (19)0.0272 (8)
H10.99850.07740.89160.033*
C21.07003 (12)0.0789 (4)0.94527 (19)0.0281 (8)
H21.0733−0.02410.94630.034*
C31.11017 (12)0.1672 (4)0.97649 (17)0.0242 (8)
C41.10261 (13)0.3154 (4)0.9727 (2)0.0397 (10)
H41.12890.38070.99280.048*
C51.05745 (16)0.3683 (4)0.9400 (3)0.0404 (12)
H51.05340.47100.93880.049*
C61.15967 (14)0.1048 (4)1.0152 (2)0.0284 (9)
H6A1.17340.09651.06480.034*
H6B1.15760.00540.99760.034*
C71.17845 (12)0.1844 (5)0.93855 (19)0.0332 (9)
H7A1.14540.22130.90510.040*
H7B1.17920.08150.92690.040*
C81.21230 (13)0.2733 (5)0.9328 (2)0.0427 (10)
H8A1.20360.26310.88570.051*
H8B1.20970.37760.94070.051*
C91.27530 (13)0.2287 (5)1.0534 (2)0.0411 (10)
H9A1.27560.33121.06660.049*
H9B1.30800.18881.08600.049*
C101.24062 (12)0.1407 (4)1.05854 (19)0.0333 (9)
H10A1.24250.03661.04960.040*
H10B1.24970.14921.10590.040*
C111.29431 (13)0.2327 (4)0.96979 (19)0.0324 (9)
C121.34343 (13)0.2060 (4)1.0214 (2)0.0336 (9)
H121.35560.18701.06800.040*
C131.37318 (14)0.2085 (4)1.0014 (2)0.0389 (10)
H131.40630.18911.03460.047*
C141.35531 (15)0.2388 (4)0.9344 (2)0.0394 (10)
H141.37560.24230.92050.047*
C151.30730 (15)0.2637 (4)0.8881 (2)0.0390 (10)
H151.29470.28300.84140.047*
C160.97696 (19)0.4129 (4)0.7541 (3)0.0389 (12)
H160.97550.31110.75970.047*
C170.99227 (15)0.4589 (4)0.7163 (2)0.0399 (10)
H171.00120.38950.69680.048*
C180.99468 (12)0.6056 (4)0.70676 (19)0.0290 (8)
C190.98089 (12)0.6997 (4)0.73640 (19)0.0319 (8)
H190.98160.80190.73090.038*
C200.96608 (13)0.6461 (4)0.77395 (19)0.0299 (8)
H200.95700.71330.79410.036*
C211.01122 (16)0.6611 (4)0.6655 (2)0.0376 (10)
H21A0.98320.67210.61640.045*
H21B1.02580.75860.68290.045*
C221.09188 (13)0.5742 (5)0.73759 (19)0.0397 (10)
H22A1.08780.54930.77360.048*
H22B1.10420.67510.74590.048*
C231.12757 (15)0.4696 (6)0.7421 (2)0.0624 (15)
H23A1.15900.47960.78780.075*
H23B1.11650.36800.73750.075*
C241.08643 (14)0.4962 (6)0.6188 (2)0.0492 (12)
H24A1.07330.39600.60860.059*
H24B1.09110.52360.58360.059*
C251.05150 (13)0.6004 (4)0.61546 (18)0.0335 (8)
H25A1.06340.70160.62200.040*
H25B1.02010.59390.56940.040*
C261.17465 (13)0.5306 (4)0.6982 (2)0.0368 (9)
C271.21847 (15)0.5353 (5)0.7642 (2)0.0427 (10)
H271.21980.51960.80420.051*
C281.21344 (16)0.5778 (5)0.6498 (2)0.0397 (10)
H281.21190.59260.60960.048*
C291.25750 (16)0.5836 (4)0.7125 (2)0.0404 (10)
H291.28560.60110.71580.049*
C301.25938 (15)0.5628 (4)0.7704 (2)0.0436 (11)
H301.28920.56760.81500.052*
C310.93184 (14)0.1620 (4)0.9388 (2)0.0361 (9)
H310.94490.09920.92270.043*
C320.91637 (13)0.1013 (4)0.9746 (2)0.0345 (9)
H320.9193−0.00060.98320.041*
C330.89661 (13)0.1890 (4)0.99785 (19)0.0296 (8)
C340.89430 (14)0.3378 (4)0.98476 (19)0.0324 (9)
H340.88150.40311.00030.039*
C350.91075 (17)0.3890 (4)0.9490 (2)0.0322 (11)
H350.90880.49080.94050.039*
C360.87977 (18)0.1253 (5)1.0372 (3)0.0372 (12)
H36A0.87070.02221.02340.045*
H36B0.90650.12731.08730.045*
C370.79610 (13)0.1850 (5)0.95317 (19)0.0377 (10)
H37A0.78810.08010.94370.045*
H37B0.80270.22090.92100.045*
C380.75448 (14)0.2670 (5)0.94099 (19)0.0450 (11)
H38A0.76180.37260.94820.054*
H38B0.72590.25230.89270.054*
C390.78663 (13)0.2243 (5)1.06098 (18)0.0360 (9)
H39A0.77930.17861.09080.043*
H39B0.79480.32781.07470.043*
C400.82859 (13)0.1474 (4)1.07100 (19)0.0318 (9)
H40A0.85720.15941.11960.038*
H40B0.82150.04191.06220.038*
C410.69918 (13)0.2184 (4)0.97106 (18)0.0319 (8)
C420.65933 (14)0.2532 (4)0.90413 (19)0.0353 (9)
H420.66300.28240.86980.042*
C430.65010 (15)0.1735 (4)1.0039 (2)0.0326 (10)
H430.64650.14461.03840.039*
C440.60962 (13)0.2053 (4)0.9389 (2)0.0357 (9)
H440.57890.20020.92880.043*
C450.61478 (14)0.2443 (4)0.8891 (2)0.0399 (10)
H450.58720.26550.84360.048*
C460.85807 (13)0.6415 (4)0.77122 (19)0.0296 (8)
H460.88300.70600.78230.035*
C470.81227 (12)0.6972 (4)0.73715 (18)0.0270 (8)
H470.80640.79770.72540.032*
C480.77520 (11)0.6066 (4)0.72029 (16)0.0232 (7)
C490.78600 (11)0.4604 (4)0.73832 (17)0.0241 (7)
H490.76160.39330.72730.029*
C500.83285 (15)0.4139 (4)0.7726 (2)0.0270 (9)
H500.83970.31390.78490.032*
C510.72491 (12)0.6655 (4)0.6807 (2)0.0257 (9)
H51A0.72560.76000.70120.031*
H51B0.71250.68350.63220.031*
C520.69999 (12)0.5694 (4)0.74789 (18)0.0335 (9)
H52A0.69370.66900.75650.040*
H52B0.73370.54500.78540.040*
C530.66746 (13)0.4623 (5)0.7488 (2)0.0479 (12)
H53A0.67650.36160.74610.057*
H53B0.67140.47220.79270.057*
C540.61010 (13)0.4890 (5)0.62463 (19)0.0429 (11)
H54A0.57620.51190.58710.051*
H54B0.61730.39150.61550.051*
C550.64248 (11)0.6029 (4)0.62611 (17)0.0276 (8)
H55A0.63730.60460.58110.033*
H55B0.63490.70070.63440.033*
C560.58360 (13)0.5241 (4)0.6999 (2)0.0349 (9)
C570.53659 (14)0.5609 (4)0.6434 (2)0.0391 (10)
H570.52790.56810.59790.047*
C580.50404 (19)0.5860 (5)0.6558 (3)0.0510 (14)
H580.47210.61010.61840.061*
C590.51660 (17)0.5769 (4)0.7216 (3)0.0517 (12)
H590.49370.59140.73020.062*
C600.56340 (17)0.5462 (4)0.7745 (2)0.0471 (11)
H600.57270.54420.82040.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.01918 (10)0.02144 (11)0.02824 (12)0.00173 (13)0.01579 (9)0.00171 (14)
Cl20.0276 (4)0.0357 (5)0.0292 (5)−0.0047 (4)0.0161 (4)−0.0045 (4)
Cl30.0321 (5)0.0246 (4)0.0327 (5)−0.0055 (4)0.0170 (4)−0.0075 (4)
O10.070 (2)0.122 (3)0.083 (3)−0.067 (2)0.060 (2)−0.063 (2)
O20.090 (3)0.102 (3)0.102 (3)0.052 (3)0.052 (3)−0.015 (3)
O30.0525 (18)0.0415 (17)0.0557 (19)−0.0073 (14)0.0273 (16)−0.0260 (15)
O40.087 (3)0.141 (4)0.047 (2)−0.040 (3)0.016 (2)0.036 (2)
O50.068 (2)0.0365 (17)0.070 (2)−0.0040 (16)0.0344 (18)−0.0245 (15)
O60.072 (2)0.127 (3)0.066 (2)−0.015 (2)0.054 (2)−0.028 (2)
O70.054 (2)0.095 (3)0.069 (2)−0.044 (2)0.0321 (19)−0.013 (2)
O80.099 (3)0.058 (2)0.046 (2)0.024 (2)0.013 (2)0.0083 (18)
N10.0239 (15)0.0237 (16)0.0340 (17)−0.0002 (13)0.0185 (14)−0.0007 (13)
N20.0174 (13)0.0258 (15)0.0247 (15)0.0010 (12)0.0108 (12)0.0026 (13)
N30.0236 (16)0.078 (3)0.0260 (17)−0.0031 (16)0.0156 (14)0.0052 (17)
N40.0385 (19)0.048 (2)0.0372 (19)−0.0057 (16)0.0275 (17)−0.0030 (16)
N50.0341 (17)0.0249 (16)0.0371 (18)−0.0026 (13)0.0260 (15)−0.0018 (14)
N60.0320 (16)0.0282 (17)0.0281 (16)0.0009 (13)0.0219 (14)0.0022 (12)
N70.0299 (19)0.160 (4)0.029 (2)0.020 (2)0.0201 (17)0.011 (2)
N80.0417 (19)0.0376 (19)0.041 (2)0.0051 (15)0.0270 (17)−0.0016 (15)
N90.0259 (15)0.0203 (15)0.0351 (17)0.0013 (12)0.0218 (14)0.0026 (13)
N100.0312 (16)0.0288 (16)0.0275 (16)0.0042 (13)0.0206 (14)0.0046 (13)
N110.0300 (17)0.068 (2)0.0257 (17)0.0036 (16)0.0192 (15)0.0062 (16)
N120.0437 (19)0.0345 (19)0.0314 (18)0.0033 (16)0.0280 (16)0.0007 (15)
N130.0242 (15)0.0233 (15)0.0250 (15)0.0018 (12)0.0144 (13)0.0013 (12)
N140.0195 (14)0.0276 (16)0.0215 (15)0.0013 (11)0.0120 (13)0.0017 (12)
N150.0219 (17)0.122 (4)0.0266 (19)−0.003 (2)0.0131 (15)0.021 (2)
N160.043 (2)0.048 (2)0.037 (2)−0.0041 (17)0.0266 (17)0.0062 (17)
C10.0208 (17)0.0207 (18)0.036 (2)−0.0029 (13)0.0151 (16)0.0011 (15)
C20.0287 (18)0.0194 (19)0.041 (2)0.0009 (15)0.0236 (17)0.0016 (16)
C30.0248 (18)0.0226 (19)0.0264 (19)0.0028 (15)0.0159 (16)0.0028 (15)
C40.0209 (19)0.023 (2)0.060 (3)−0.0054 (16)0.0160 (19)−0.0059 (19)
C50.028 (2)0.0152 (19)0.067 (3)0.0008 (17)0.023 (2)−0.0042 (19)
C60.023 (2)0.0222 (18)0.039 (2)0.0034 (16)0.0182 (19)0.0045 (17)
C70.0215 (18)0.046 (2)0.028 (2)0.0017 (17)0.0130 (16)−0.0028 (18)
C80.030 (2)0.063 (3)0.031 (2)0.000 (2)0.0166 (19)0.009 (2)
C90.0205 (19)0.063 (3)0.036 (2)−0.0066 (18)0.0150 (18)−0.001 (2)
C100.0239 (19)0.046 (2)0.028 (2)0.0039 (16)0.0142 (17)0.0073 (17)
C110.033 (2)0.035 (2)0.032 (2)−0.0071 (16)0.0204 (18)−0.0062 (17)
C120.034 (2)0.033 (2)0.037 (2)−0.0074 (17)0.0237 (19)−0.0075 (17)
C130.034 (2)0.030 (2)0.057 (3)−0.0085 (17)0.029 (2)−0.015 (2)
C140.052 (3)0.031 (2)0.057 (3)−0.0052 (19)0.044 (2)−0.0086 (19)
C150.048 (3)0.039 (2)0.044 (2)−0.0062 (19)0.035 (2)−0.0041 (19)
C160.060 (3)0.024 (2)0.061 (3)−0.0109 (19)0.052 (3)−0.007 (2)
C170.056 (3)0.026 (2)0.062 (3)−0.008 (2)0.048 (2)−0.012 (2)
C180.0266 (18)0.0291 (19)0.036 (2)0.0028 (17)0.0213 (16)0.0065 (18)
C190.039 (2)0.0249 (19)0.047 (2)0.0066 (17)0.033 (2)0.0072 (18)
C200.034 (2)0.0236 (18)0.040 (2)0.0045 (15)0.0264 (19)0.0028 (16)
C210.051 (3)0.031 (2)0.051 (3)0.0098 (19)0.041 (2)0.013 (2)
C220.033 (2)0.061 (3)0.028 (2)−0.0069 (19)0.0199 (18)−0.0059 (19)
C230.037 (2)0.126 (5)0.030 (2)0.025 (3)0.023 (2)0.015 (3)
C240.035 (2)0.089 (4)0.031 (2)0.008 (2)0.024 (2)−0.005 (2)
C250.0303 (19)0.048 (2)0.0258 (19)−0.0039 (18)0.0186 (16)−0.0014 (18)
C260.036 (2)0.042 (2)0.037 (2)0.0125 (18)0.024 (2)0.0007 (19)
C270.041 (2)0.054 (3)0.035 (2)0.008 (2)0.024 (2)0.000 (2)
C280.049 (3)0.033 (2)0.049 (3)−0.0055 (18)0.036 (2)−0.0032 (18)
C290.038 (2)0.025 (2)0.053 (3)−0.0047 (18)0.024 (2)−0.0035 (19)
C300.041 (2)0.033 (2)0.041 (3)−0.0019 (18)0.017 (2)−0.0059 (18)
C310.044 (2)0.027 (2)0.050 (3)0.0057 (18)0.036 (2)0.0023 (18)
C320.045 (2)0.0186 (17)0.052 (2)0.0042 (18)0.036 (2)0.0075 (18)
C330.0322 (19)0.030 (2)0.030 (2)0.0024 (17)0.0207 (17)0.0048 (17)
C340.044 (2)0.026 (2)0.039 (2)0.0034 (18)0.031 (2)0.0035 (18)
C350.040 (3)0.018 (2)0.044 (3)−0.0003 (16)0.029 (2)0.0013 (17)
C360.055 (3)0.026 (2)0.047 (3)0.0066 (19)0.039 (2)0.0086 (19)
C370.042 (2)0.051 (3)0.028 (2)−0.002 (2)0.0251 (19)0.0001 (19)
C380.036 (2)0.077 (3)0.024 (2)0.006 (2)0.0183 (18)0.013 (2)
C390.036 (2)0.052 (3)0.023 (2)0.0035 (18)0.0198 (18)0.0007 (18)
C400.036 (2)0.036 (2)0.025 (2)0.0016 (17)0.0195 (18)0.0068 (16)
C410.038 (2)0.035 (2)0.027 (2)0.0008 (17)0.0218 (18)−0.0016 (16)
C420.044 (2)0.037 (2)0.028 (2)−0.0003 (18)0.0226 (19)0.0010 (17)
C430.049 (3)0.022 (2)0.042 (3)−0.0039 (19)0.035 (2)−0.0027 (18)
C440.033 (2)0.0233 (19)0.050 (3)−0.0039 (16)0.024 (2)−0.0056 (18)
C450.036 (2)0.032 (2)0.034 (2)0.0004 (18)0.0117 (19)−0.0040 (18)
C460.0278 (19)0.0271 (19)0.037 (2)−0.0060 (15)0.0212 (17)−0.0006 (16)
C470.0259 (18)0.0238 (18)0.032 (2)−0.0006 (15)0.0180 (16)0.0037 (16)
C480.0247 (17)0.0234 (17)0.0207 (17)−0.0015 (15)0.0133 (15)−0.0008 (15)
C490.0203 (17)0.0209 (17)0.0279 (19)−0.0017 (14)0.0127 (15)−0.0006 (15)
C500.025 (2)0.0175 (19)0.032 (2)−0.0021 (15)0.0131 (17)0.0007 (16)
C510.0193 (19)0.023 (2)0.031 (2)0.0034 (15)0.0128 (17)0.0055 (17)
C520.0198 (17)0.048 (3)0.0270 (19)0.0060 (16)0.0109 (16)0.0012 (17)
C530.027 (2)0.085 (3)0.025 (2)−0.004 (2)0.0127 (18)0.016 (2)
C540.0239 (19)0.072 (3)0.027 (2)−0.011 (2)0.0122 (17)0.006 (2)
C550.0207 (16)0.037 (2)0.0219 (17)0.0029 (16)0.0109 (14)−0.0020 (16)
C560.036 (2)0.035 (2)0.037 (2)−0.0055 (17)0.0228 (19)0.0108 (18)
C570.035 (2)0.030 (2)0.039 (2)−0.0008 (17)0.0152 (19)0.0081 (17)
C580.037 (3)0.032 (3)0.074 (4)0.010 (2)0.028 (3)0.001 (2)
C590.058 (3)0.032 (3)0.086 (4)0.000 (2)0.054 (3)−0.008 (2)
C600.067 (3)0.036 (2)0.059 (3)−0.007 (2)0.048 (3)−0.002 (2)
Geometric parameters (Å, °) top
Cd1—N132.310 (3)C17—C181.377 (5)
Cd1—N12.320 (3)C17—H170.9500
Cd1—N52.321 (3)C18—C191.380 (5)
Cd1—N92.331 (3)C18—C211.510 (5)
Cd1—O52.388 (3)C19—C201.377 (5)
Cd1—O32.391 (3)C19—H190.9500
Cl2—O41.394 (3)C20—H200.9500
Cl2—O21.395 (3)C21—H21A0.9900
Cl2—O11.406 (3)C21—H21B0.9900
Cl2—O31.439 (3)C22—C231.525 (6)
Cl3—O71.412 (3)C22—H22A0.9900
Cl3—O51.415 (3)C22—H22B0.9900
Cl3—O61.420 (3)C23—H23A0.9900
Cl3—O81.426 (3)C23—H23B0.9900
N1—C11.329 (4)C24—C251.514 (5)
N1—C51.356 (5)C24—H24A0.9900
N2—C101.457 (4)C24—H24B0.9900
N2—C61.465 (5)C25—H25A0.9900
N2—C71.465 (4)C25—H25B0.9900
N3—C111.383 (4)C26—C271.399 (5)
N3—C91.442 (5)C27—C301.369 (6)
N3—C81.463 (5)C27—H270.9500
N4—C111.333 (5)C28—C291.367 (6)
N4—C151.346 (5)C28—H280.9500
N5—C161.331 (5)C29—C301.374 (6)
N5—C201.340 (4)C29—H290.9500
N6—C211.459 (5)C30—H300.9500
N6—C221.460 (5)C31—C321.383 (5)
N6—C251.465 (4)C31—H310.9500
N7—C261.366 (5)C32—C331.380 (5)
N7—C231.446 (5)C32—H320.9500
N7—C241.469 (5)C33—C341.392 (5)
N8—C281.332 (5)C33—C361.504 (5)
N8—C261.355 (5)C34—C351.376 (6)
N9—C311.333 (5)C34—H340.9500
N9—C351.336 (5)C35—H350.9500
N10—C401.454 (4)C36—H36A0.9900
N10—C361.464 (5)C36—H36B0.9900
N10—C371.472 (4)C37—C381.502 (5)
N11—C411.383 (4)C37—H37A0.9900
N11—C391.459 (5)C37—H37B0.9900
N11—C381.461 (5)C38—H38A0.9900
N12—C431.351 (5)C38—H38B0.9900
N12—C411.358 (4)C39—C401.511 (5)
N13—C501.327 (5)C39—H39A0.9900
N13—C461.346 (4)C39—H39B0.9900
N14—C521.458 (4)C40—H40A0.9900
N14—C551.463 (4)C40—H40B0.9900
N14—C511.470 (5)C41—C421.398 (5)
N15—C561.377 (5)C42—C451.373 (5)
N15—C531.455 (5)C42—H420.9500
N15—C541.455 (5)C43—C441.374 (5)
N16—C561.342 (5)C43—H430.9500
N16—C601.350 (5)C44—C451.366 (5)
C1—C21.379 (5)C44—H440.9500
C1—H10.9500C45—H450.9500
C2—C31.388 (5)C46—C471.386 (5)
C2—H20.9500C46—H460.9500
C3—C41.377 (5)C47—C481.379 (5)
C3—C61.502 (5)C47—H470.9500
C4—C51.362 (6)C48—C491.391 (5)
C4—H40.9500C48—C511.510 (5)
C5—H50.9500C49—C501.386 (5)
C6—H6A0.9900C49—H490.9500
C6—H6B0.9900C50—H500.9500
C7—C81.510 (5)C51—H51A0.9900
C7—H7A0.9900C51—H51B0.9900
C7—H7B0.9900C52—C531.512 (5)
C8—H8A0.9900C52—H52A0.9900
C8—H8B0.9900C52—H52B0.9900
C9—C101.522 (5)C53—H53A0.9900
C9—H9A0.9900C53—H53B0.9900
C9—H9B0.9900C54—C551.525 (5)
C10—H10A0.9900C54—H54A0.9900
C10—H10B0.9900C54—H54B0.9900
C11—C121.412 (5)C55—H55A0.9900
C12—C131.385 (5)C55—H55B0.9900
C12—H120.9500C56—C571.409 (5)
C13—C141.370 (6)C57—C581.359 (7)
C13—H130.9500C57—H570.9500
C14—C151.366 (6)C58—C591.374 (7)
C14—H140.9500C58—H580.9500
C15—H150.9500C59—C601.371 (6)
C16—C171.371 (6)C59—H590.9500
C16—H160.9500C60—H600.9500
N13—Cd1—N1175.67 (11)H22A—C22—H22B108.2
N13—Cd1—N595.14 (10)N7—C23—C22110.5 (4)
N1—Cd1—N585.84 (10)N7—C23—H23A109.6
N13—Cd1—N986.92 (10)C22—C23—H23A109.6
N1—Cd1—N992.33 (10)N7—C23—H23B109.6
N5—Cd1—N9176.34 (11)C22—C23—H23B109.6
N13—Cd1—O596.23 (10)H23A—C23—H23B108.1
N1—Cd1—O587.99 (11)N7—C24—C25110.1 (3)
N5—Cd1—O589.26 (11)N7—C24—H24A109.6
N9—Cd1—O587.51 (12)C25—C24—H24A109.6
N13—Cd1—O389.72 (10)N7—C24—H24B109.6
N1—Cd1—O385.96 (10)C25—C24—H24B109.6
N5—Cd1—O3102.09 (11)H24A—C24—H24B108.2
N9—Cd1—O380.92 (10)N6—C25—C24110.1 (3)
O5—Cd1—O3166.69 (12)N6—C25—H25A109.6
O4—Cl2—O2108.8 (3)C24—C25—H25A109.6
O4—Cl2—O1110.1 (2)N6—C25—H25B109.6
O2—Cl2—O1110.7 (3)C24—C25—H25B109.6
O4—Cl2—O3109.9 (2)H25A—C25—H25B108.2
O2—Cl2—O3108.1 (2)N8—C26—N7116.9 (3)
O1—Cl2—O3109.27 (19)N8—C26—C27120.6 (4)
O7—Cl3—O5109.5 (2)N7—C26—C27122.5 (4)
O7—Cl3—O6109.3 (2)C30—C27—C26119.2 (4)
O5—Cl3—O6108.1 (2)C30—C27—H27120.4
O7—Cl3—O8110.9 (2)C26—C27—H27120.4
O5—Cl3—O8108.6 (2)N8—C28—C29124.9 (4)
O6—Cl3—O8110.5 (3)N8—C28—H28117.6
Cl2—O3—Cd1142.7 (2)C29—C28—H28117.6
Cl3—O5—Cd1152.1 (2)C28—C29—C30117.1 (4)
C1—N1—C5115.8 (3)C28—C29—H29121.5
C1—N1—Cd1126.8 (2)C30—C29—H29121.5
C5—N1—Cd1117.3 (2)C27—C30—C29120.4 (4)
C10—N2—C6109.0 (3)C27—C30—H30119.8
C10—N2—C7109.9 (3)C29—C30—H30119.8
C6—N2—C7111.3 (3)N9—C31—C32123.2 (3)
C11—N3—C9122.5 (3)N9—C31—H31118.4
C11—N3—C8120.1 (3)C32—C31—H31118.4
C9—N3—C8112.1 (3)C33—C32—C31120.0 (4)
C11—N4—C15117.7 (3)C33—C32—H32120.0
C16—N5—C20116.7 (3)C31—C32—H32120.0
C16—N5—Cd1117.4 (3)C32—C33—C34117.0 (3)
C20—N5—Cd1125.8 (2)C32—C33—C36120.8 (3)
C21—N6—C22110.1 (3)C34—C33—C36122.2 (3)
C21—N6—C25110.8 (3)C35—C34—C33119.2 (4)
C22—N6—C25110.2 (3)C35—C34—H34120.4
C26—N7—C23125.2 (3)C33—C34—H34120.4
C26—N7—C24122.7 (3)N9—C35—C34124.0 (3)
C23—N7—C24112.1 (3)N9—C35—H35118.0
C28—N8—C26117.8 (4)C34—C35—H35118.0
C31—N9—C35116.6 (3)N10—C36—C33112.7 (3)
C31—N9—Cd1122.7 (2)N10—C36—H36A109.1
C35—N9—Cd1120.0 (2)C33—C36—H36A109.1
C40—N10—C36109.2 (3)N10—C36—H36B109.1
C40—N10—C37108.4 (3)C33—C36—H36B109.1
C36—N10—C37111.0 (3)H36A—C36—H36B107.8
C41—N11—C39120.6 (3)N10—C37—C38110.6 (3)
C41—N11—C38121.4 (3)N10—C37—H37A109.5
C39—N11—C38112.7 (3)C38—C37—H37A109.5
C43—N12—C41117.7 (3)N10—C37—H37B109.5
C50—N13—C46116.6 (3)C38—C37—H37B109.5
C50—N13—Cd1117.8 (2)H37A—C37—H37B108.1
C46—N13—Cd1125.5 (2)N11—C38—C37109.8 (3)
C52—N14—C55109.5 (3)N11—C38—H38A109.7
C52—N14—C51111.6 (3)C37—C38—H38A109.7
C55—N14—C51110.5 (3)N11—C38—H38B109.7
C56—N15—C53122.4 (3)C37—C38—H38B109.7
C56—N15—C54124.7 (3)H38A—C38—H38B108.2
C53—N15—C54112.6 (3)N11—C39—C40110.2 (3)
C56—N16—C60117.7 (4)N11—C39—H39A109.6
N1—C1—C2123.6 (3)C40—C39—H39A109.6
N1—C1—H1118.2N11—C39—H39B109.6
C2—C1—H1118.2C40—C39—H39B109.6
C1—C2—C3120.0 (3)H39A—C39—H39B108.1
C1—C2—H2120.0N10—C40—C39111.9 (3)
C3—C2—H2120.0N10—C40—H40A109.2
C4—C3—C2116.7 (3)C39—C40—H40A109.2
C4—C3—C6121.4 (3)N10—C40—H40B109.2
C2—C3—C6121.8 (3)C39—C40—H40B109.2
C5—C4—C3120.0 (3)H40A—C40—H40B107.9
C5—C4—H4120.0N12—C41—N11116.7 (3)
C3—C4—H4120.0N12—C41—C42121.5 (3)
N1—C5—C4124.0 (4)N11—C41—C42121.7 (3)
N1—C5—H5118.0C45—C42—C41118.5 (4)
C4—C5—H5118.0C45—C42—H42120.8
N2—C6—C3113.3 (3)C41—C42—H42120.8
N2—C6—H6A108.9N12—C43—C44123.4 (4)
C3—C6—H6A108.9N12—C43—H43118.3
N2—C6—H6B108.9C44—C43—H43118.3
C3—C6—H6B108.9C45—C44—C43118.2 (4)
H6A—C6—H6B107.7C45—C44—H44120.9
N2—C7—C8110.8 (3)C43—C44—H44120.9
N2—C7—H7A109.5C44—C45—C42120.7 (4)
C8—C7—H7A109.5C44—C45—H45119.6
N2—C7—H7B109.5C42—C45—H45119.6
C8—C7—H7B109.5N13—C46—C47123.0 (3)
H7A—C7—H7B108.1N13—C46—H46118.5
N3—C8—C7110.0 (3)C47—C46—H46118.5
N3—C8—H8A109.7C48—C47—C46120.0 (3)
C7—C8—H8A109.7C48—C47—H47120.0
N3—C8—H8B109.7C46—C47—H47120.0
C7—C8—H8B109.7C47—C48—C49117.3 (3)
H8A—C8—H8B108.2C47—C48—C51120.2 (3)
N3—C9—C10110.5 (3)C49—C48—C51122.5 (3)
N3—C9—H9A109.6C50—C49—C48119.0 (3)
C10—C9—H9A109.6C50—C49—H49120.5
N3—C9—H9B109.6C48—C49—H49120.5
C10—C9—H9B109.6N13—C50—C49124.1 (3)
H9A—C9—H9B108.1N13—C50—H50117.9
N2—C10—C9110.8 (3)C49—C50—H50117.9
N2—C10—H10A109.5N14—C51—C48112.8 (3)
C9—C10—H10A109.5N14—C51—H51A109.0
N2—C10—H10B109.5C48—C51—H51A109.0
C9—C10—H10B109.5N14—C51—H51B109.0
H10A—C10—H10B108.1C48—C51—H51B109.0
N4—C11—N3116.2 (3)H51A—C51—H51B107.8
N4—C11—C12122.3 (3)N14—C52—C53110.9 (3)
N3—C11—C12121.4 (3)N14—C52—H52A109.5
C13—C12—C11117.3 (4)C53—C52—H52A109.5
C13—C12—H12121.3N14—C52—H52B109.5
C11—C12—H12121.3C53—C52—H52B109.5
C14—C13—C12120.7 (4)H52A—C52—H52B108.0
C14—C13—H13119.7N15—C53—C52110.8 (3)
C12—C13—H13119.7N15—C53—H53A109.5
C15—C14—C13117.8 (4)C52—C53—H53A109.5
C15—C14—H14121.1N15—C53—H53B109.5
C13—C14—H14121.1C52—C53—H53B109.5
N4—C15—C14124.1 (4)H53A—C53—H53B108.1
N4—C15—H15117.9N15—C54—C55109.5 (3)
C14—C15—H15117.9N15—C54—H54A109.8
N5—C16—C17123.6 (4)C55—C54—H54A109.8
N5—C16—H16118.2N15—C54—H54B109.8
C17—C16—H16118.2C55—C54—H54B109.8
C16—C17—C18120.0 (4)H54A—C54—H54B108.2
C16—C17—H17120.0N14—C55—C54108.8 (3)
C18—C17—H17120.0N14—C55—H55A109.9
C17—C18—C19116.7 (3)C54—C55—H55A109.9
C17—C18—C21121.8 (3)N14—C55—H55B109.9
C19—C18—C21121.6 (3)C54—C55—H55B109.9
C20—C19—C18120.3 (3)H55A—C55—H55B108.3
C20—C19—H19119.8N16—C56—N15116.7 (3)
C18—C19—H19119.8N16—C56—C57121.8 (4)
N5—C20—C19122.7 (3)N15—C56—C57121.5 (4)
N5—C20—H20118.7C58—C57—C56118.1 (4)
C19—C20—H20118.7C58—C57—H57120.9
N6—C21—C18112.7 (3)C56—C57—H57120.9
N6—C21—H21A109.1C57—C58—C59121.1 (5)
C18—C21—H21A109.1C57—C58—H58119.5
N6—C21—H21B109.1C59—C58—H58119.5
C18—C21—H21B109.1C60—C59—C58117.6 (4)
H21A—C21—H21B107.8C60—C59—H59121.2
N6—C22—C23110.0 (3)C58—C59—H59121.2
N6—C22—H22A109.7N16—C60—C59123.6 (4)
C23—C22—H22A109.7N16—C60—H60118.2
N6—C22—H22B109.7C59—C60—H60118.2
C23—C22—H22B109.7
O4—Cl2—O3—Cd1−17.1 (4)C19—C18—C21—N6150.0 (4)
O1—Cl2—O3—Cd1−137.9 (3)C21—N6—C22—C23178.3 (3)
N13—Cd1—O3—Cl287.4 (3)C25—N6—C22—C23−59.1 (4)
N1—Cd1—O3—Cl2−92.7 (3)C26—N7—C23—C22124.2 (5)
N5—Cd1—O3—Cl2−7.8 (3)C24—N7—C23—C22−55.7 (6)
N9—Cd1—O3—Cl2174.3 (3)N6—C22—C23—N756.9 (5)
O5—Cd1—O3—Cl2−155.8 (4)C26—N7—C24—C25−124.0 (5)
O7—Cl3—O5—Cd1−149.1 (5)C23—N7—C24—C2555.9 (6)
O6—Cl3—O5—Cd192.0 (5)C21—N6—C25—C24−178.3 (3)
O8—Cl3—O5—Cd1−27.9 (6)C22—N6—C25—C2459.5 (4)
N13—Cd1—O5—Cl3−11.3 (5)N7—C24—C25—N6−57.0 (5)
N1—Cd1—O5—Cl3169.6 (5)C28—N8—C26—N7−177.9 (4)
N5—Cd1—O5—Cl383.7 (5)C28—N8—C26—C270.7 (6)
N9—Cd1—O5—Cl3−98.0 (5)C23—N7—C26—N8178.3 (5)
O3—Cd1—O5—Cl3−127.5 (5)C24—N7—C26—N8−1.8 (7)
N5—Cd1—N1—C1−116.7 (3)C23—N7—C26—C27−0.3 (8)
N9—Cd1—N1—C166.5 (3)C24—N7—C26—C27179.6 (4)
O5—Cd1—N1—C1153.9 (3)N8—C26—C27—C30−0.1 (6)
O3—Cd1—N1—C1−14.2 (3)N7—C26—C27—C30178.5 (4)
N5—Cd1—N1—C559.7 (3)C26—N8—C28—C29−0.5 (6)
N9—Cd1—N1—C5−117.1 (3)N8—C28—C29—C30−0.4 (6)
O5—Cd1—N1—C5−29.7 (3)C26—C27—C30—C29−0.9 (6)
O3—Cd1—N1—C5162.1 (3)C28—C29—C30—C271.1 (6)
N13—Cd1—N5—C16−123.3 (3)C35—N9—C31—C320.1 (6)
N1—Cd1—N5—C1652.5 (3)Cd1—N9—C31—C32−170.4 (3)
O5—Cd1—N5—C16140.5 (3)N9—C31—C32—C330.8 (6)
O3—Cd1—N5—C16−32.5 (3)C31—C32—C33—C34−1.4 (6)
N13—Cd1—N5—C2060.9 (3)C31—C32—C33—C36−179.7 (4)
N1—Cd1—N5—C20−123.4 (3)C32—C33—C34—C351.0 (6)
O5—Cd1—N5—C20−35.3 (3)C36—C33—C34—C35179.4 (4)
O3—Cd1—N5—C20151.7 (3)C31—N9—C35—C34−0.5 (6)
N13—Cd1—N9—C31123.1 (3)Cd1—N9—C35—C34170.3 (3)
N1—Cd1—N9—C31−52.6 (3)C33—C34—C35—N9−0.1 (6)
O5—Cd1—N9—C31−140.5 (3)C40—N10—C36—C33−173.2 (3)
O3—Cd1—N9—C3132.9 (3)C37—N10—C36—C3367.4 (4)
N13—Cd1—N9—C35−47.1 (3)C32—C33—C36—N10−148.3 (4)
N1—Cd1—N9—C35137.1 (3)C34—C33—C36—N1033.4 (6)
O5—Cd1—N9—C3549.3 (3)C40—N10—C37—C3860.5 (4)
O3—Cd1—N9—C35−137.3 (3)C36—N10—C37—C38−179.6 (3)
N5—Cd1—N13—C50134.0 (3)C41—N11—C38—C37−150.2 (4)
N9—Cd1—N13—C50−49.1 (3)C39—N11—C38—C3755.3 (5)
O5—Cd1—N13—C50−136.2 (3)N10—C37—C38—N11−58.7 (4)
O3—Cd1—N13—C5031.9 (3)C41—N11—C39—C40152.0 (4)
N5—Cd1—N13—C46−49.2 (3)C38—N11—C39—C40−53.3 (4)
N9—Cd1—N13—C46127.7 (3)C36—N10—C40—C39−180.0 (3)
O5—Cd1—N13—C4640.6 (3)C37—N10—C40—C39−59.0 (4)
O3—Cd1—N13—C46−151.3 (3)N11—C39—C40—N1055.6 (4)
C5—N1—C1—C20.1 (6)C43—N12—C41—N11−175.4 (3)
Cd1—N1—C1—C2176.5 (3)C43—N12—C41—C422.6 (5)
N1—C1—C2—C3−0.2 (6)C39—N11—C41—N12−21.3 (5)
C1—C2—C3—C4−0.2 (5)C38—N11—C41—N12−173.8 (4)
C1—C2—C3—C6177.3 (3)C39—N11—C41—C42160.7 (4)
C2—C3—C4—C50.6 (6)C38—N11—C41—C428.3 (6)
C6—C3—C4—C5−176.8 (4)N12—C41—C42—C45−2.3 (6)
C1—N1—C5—C40.4 (7)N11—C41—C42—C45175.6 (4)
Cd1—N1—C5—C4−176.4 (4)C41—N12—C43—C44−2.0 (6)
C3—C4—C5—N1−0.8 (7)N12—C43—C44—C451.1 (6)
C10—N2—C6—C3168.5 (3)C43—C44—C45—C42−0.8 (6)
C7—N2—C6—C3−70.1 (4)C41—C42—C45—C441.4 (6)
C4—C3—C6—N2−36.9 (5)C50—N13—C46—C470.3 (5)
C2—C3—C6—N2145.8 (3)Cd1—N13—C46—C47−176.5 (3)
C10—N2—C7—C8−58.2 (4)N13—C46—C47—C480.0 (5)
C6—N2—C7—C8−179.1 (3)C46—C47—C48—C49−0.6 (5)
C11—N3—C8—C7148.9 (4)C46—C47—C48—C51−177.6 (3)
C9—N3—C8—C7−56.2 (5)C47—C48—C49—C500.8 (5)
N2—C7—C8—N356.9 (4)C51—C48—C49—C50177.8 (4)
C11—N3—C9—C10−150.0 (4)C46—N13—C50—C490.0 (6)
C8—N3—C9—C1055.8 (5)Cd1—N13—C50—C49177.0 (3)
C6—N2—C10—C9179.8 (3)C48—C49—C50—N13−0.5 (6)
C7—N2—C10—C957.6 (4)C52—N14—C51—C4876.1 (4)
N3—C9—C10—N2−56.5 (4)C55—N14—C51—C48−161.9 (3)
C15—N4—C11—N3−176.1 (3)C47—C48—C51—N14−166.4 (3)
C15—N4—C11—C121.4 (6)C49—C48—C51—N1416.7 (5)
C9—N3—C11—N4−164.0 (4)C55—N14—C52—C5359.5 (4)
C8—N3—C11—N4−11.8 (5)C51—N14—C52—C53−177.9 (3)
C9—N3—C11—C1218.4 (6)C56—N15—C53—C52−119.4 (4)
C8—N3—C11—C12170.6 (4)C54—N15—C53—C5253.7 (5)
N4—C11—C12—C13−1.4 (6)N14—C52—C53—N15−54.6 (5)
N3—C11—C12—C13176.0 (4)C56—N15—C54—C55116.4 (4)
C11—C12—C13—C141.2 (6)C53—N15—C54—C55−56.5 (5)
C12—C13—C14—C15−1.1 (6)C52—N14—C55—C54−61.8 (4)
C11—N4—C15—C14−1.3 (6)C51—N14—C55—C54174.9 (3)
C13—C14—C15—N41.1 (6)N15—C54—C55—N1460.0 (4)
C20—N5—C16—C170.5 (7)C60—N16—C56—N15−176.7 (4)
Cd1—N5—C16—C17−175.7 (4)C60—N16—C56—C571.6 (6)
N5—C16—C17—C18−0.3 (8)C53—N15—C56—N16−7.2 (6)
C16—C17—C18—C19−0.3 (6)C54—N15—C56—N16−179.5 (4)
C16—C17—C18—C21−179.9 (4)C53—N15—C56—C57174.5 (4)
C17—C18—C19—C200.6 (5)C54—N15—C56—C572.2 (7)
C21—C18—C19—C20−179.8 (4)N16—C56—C57—C58−2.4 (6)
C16—N5—C20—C19−0.1 (5)N15—C56—C57—C58175.8 (4)
Cd1—N5—C20—C19175.7 (3)C56—C57—C58—C590.5 (6)
C18—C19—C20—N5−0.4 (6)C57—C58—C59—C602.0 (6)
C22—N6—C21—C18−72.6 (4)C56—N16—C60—C591.1 (6)
C25—N6—C21—C18165.2 (3)C58—C59—C60—N16−2.9 (6)
C17—C18—C21—N6−30.5 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C29—H29···O1i0.952.543.406 (6)152
C54—H54A···O7ii0.992.573.348 (5)135
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x−1/2, −y+3/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C29—H29···O1i0.952.543.406 (6)152
C54—H54A···O7ii0.992.573.348 (5)135
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x−1/2, −y+3/2, z−1/2.
Acknowledgements top

The authors gratefully acknowledge the donors of the American Chemical Society Petroleum Research Fund for funding this work.

references
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