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Acta Cryst. (2009). E65, m234    [ doi:10.1107/S1600536809002700 ]

trans-{1,8-Bis[(R)-[alpha]-methylbenzyl]-1,3,6,8,10,13-hexaazacyclotetradecane}dithiocyanatonickel(II)

J. W. Shin and K. S. Min

Abstract top

The title compound, [Ni(NCS)2(C24H38N6)], is a thiocyanate-coordinated azamacrocyclic nickel(II) complex. There are two independent molecules in the asymmetric unit and their bond lengths and angles are similar. Both Ni atoms have a tetragonally distorted octahedral geometry, in which the NiII ion is coordinated by the four secondary N atoms of the azamacrocyclic ligand and by two N atoms of the thiocyanate ions. The average equatorial Ni-N bond lengths are shorter than the average axial Ni-N bond lengths [2.071 (1) and 2.115 (2) Å, respectively]. N-H...S hydrogen-bonding interactions between a secondary amine N atom and the adjacent thiocyanate ion leads to a polymeric chain along [100].

Comment top

Chiral complexes have attracted considerable attention in chemistry and material science because of their potential applications for molecular recognition, catalysis, and separation (Lehn, 1995; Katsuki et al., 2000). Very recently lanthanide metal complexes with chiral ligands have been studied in the self-assembly of luminescent materials (Leonard et al., 2007). However, the study of chiral macrocyclic metal complexes has been limited due to the difficulty of preparation, although these complexes can be utilized as chiral building blocks (Du et al., 2003; Gao et al., 2005). Here, we report the synthesis and crystal structure of the nickel(II) azamacrocyclic chiral complex, trans-dithiocyanato(1,8-di(R-α-methylbenzyl)- 1,3,6,8,10,13-hexaazacyclotetradecane)nickel(II), with two thiocyanate ions axially.

In the title compound, the coordination geometry around the nickel(II) ion is a tetragonally distorted octahedron in which the nickel(II) ion is coordinated to the four secondary N atoms of the azamacrocyclic ligand in a square-planar fashion and two N atoms from the thiocyanate ions at the axial positions as shown in Figure 1. The average Ni—Neq and Ni—Nax bond distances are 2.071 (1) and 2.115 (2) Å, respectively. The former is slightly less than the latter, which can be attributed to the Jahn-Teller distortion of the nickel(II) ion and/or the ring contraction of the azamacrocyclic ligand. In the coordinated thiocyanate ions, the average N—C and C—S bond distances are 1.166 (3) and 1.621 (3) Å, respectively. The former is very similar to a CN triple bond length, while the latter is slightly shorter than the normal CS single bond distance (Stølevik & Postmyr, 1997; Banerjee & Zubieta, 2004). The pendant arms of the azamacrocyclic ligand have chiral carbon atoms (R type). All thiocyanate ions binding nickel(II) ions axially are involved in N—H···S hydrogen bonding interactions (Table 1), which give rise to one-dimensional polymeric chains propagating along the a axis (Figure 2). The shortest Ni···Ni intrachain separation within the hydrogen-bonded one-dimensional polymer is 8.531 (1) Å and is about 5% longer than the shortest interchain Ni···Ni distance of 8.166 (1) Å.

Related literature top

For related literature, see: Banerjee & Zubieta (2004); Du et al. (2003); Gao et al. (2005); Han et al. (2008); Katsuki et al. (2000); Lehn (1995); Leonard et al. (2007); Stølevik & Postmyr (1997).

Experimental top

The title compound is prepared as follows: To an MeCN solution (10 ml) of [Ni(C24H38N6)](ClO4)2 (0.10 g, 0.15 mmol) (Han et al., 2008) was added dropwise an aqueous solution (10 ml) containing NaSCN (0.024 g, 0.30 mmol) at ambient temperature. The color of the solution changed from yellow to pale pink. The mixture was stirred for 30 min during which time a pink precipitate formed which was collected by filtration, washed with MeCN and water, and dried in air. Single crystals of the title compound suitable for X-ray crystallography were grown by layering of the MeCN solution of [Ni(C24H38N6)](ClO4)2 on the aqueous solution of NaSCN within one week.

Refinement top

All H atoms in the title compound were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 (ring H atoms) or 0.99–1.00 (open chain H atoms) Å and N—H distance of 0.93 Å, and with Uiso(H) values of 1.2 times the equivalent anisotropic displacement parameters of the parent C and N atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the molecular title compound with atomic numbering scheme and ellipsoids at 40% probability.
[Figure 2] Fig. 2. Perspective view of the title compound showing a one-dimensional chain formed by N—H···S hydrogen bonding interactions.
trans-{1,8-Bis[(R)-α-methylbenzyl]-1,3,6,8,10,13- hexaazacyclotetradecane}dithiocyanatonickel(II) top
Crystal data top
[Ni(NCS)2(C24H38N6)]F(000) = 2480
Mr = 585.47Dx = 1.353 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6933 reflections
a = 8.5313 (5) Åθ = 2.6–22.8°
b = 15.3141 (10) ŵ = 0.85 mm−1
c = 44.004 (3) ÅT = 173 K
V = 5749.1 (6) Å3Block, violet
Z = 80.36 × 0.17 × 0.16 mm
Data collection top
Siemens SMART CCD
diffractometer		14300 independent reflections
Radiation source: fine-focus sealed tube8093 reflections with I > 2σ(I)
graphiteRint = 0.103
φ and ω scansθmax = 28.4°, θmin = 0.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→10
Tmin = 0.679, Tmax = 0.873k = −20→20
43415 measured reflectionsl = −58→43
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)] = 0.057H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0358P)2 + 2.5654P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
14300 reflectionsΔρmax = 0.81 e Å−3
668 parametersΔρmin = −0.93 e Å−3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.004 (17)
Crystal data top
[Ni(NCS)2(C24H38N6)]V = 5749.1 (6) Å3
Mr = 585.47Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 8.5313 (5) ŵ = 0.85 mm−1
b = 15.3141 (10) ÅT = 173 K
c = 44.004 (3) Å0.36 × 0.17 × 0.16 mm
Data collection top
Siemens SMART CCD
diffractometer		14300 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		8093 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.873Rint = 0.103
43415 measured reflectionsθmax = 28.4°
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.149Δρmax = 0.81 e Å−3
S = 1.04Δρmin = −0.93 e Å−3
14300 reflectionsAbsolute structure: Flack (1983)
668 parametersFlack parameter: −0.004 (17)
0 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
Ni1−0.42128 (7)−0.26127 (4)−0.137939 (15)0.02628 (15)
N1−0.2552 (5)−0.2772 (3)−0.20285 (10)0.0322 (11)
N2−0.4025 (5)−0.3641 (3)−0.16856 (10)0.0304 (10)
H2−0.3118−0.3948−0.16380.037*
N3−0.5759 (5)−0.3415 (2)−0.11490 (10)0.0282 (10)
H3−0.6770−0.3229−0.11940.034*
N4−0.5705 (5)−0.2512 (3)−0.06892 (10)0.0365 (10)
N5−0.4383 (5)−0.1595 (3)−0.10661 (10)0.0335 (11)
H5−0.5298−0.1288−0.11090.040*
N6−0.2683 (5)−0.1803 (3)−0.16088 (10)0.0280 (10)
H6−0.1672−0.1980−0.15590.034*
N7−0.2264 (5)−0.3164 (3)−0.11474 (11)0.0375 (12)
N8−0.6143 (5)−0.2084 (3)−0.16108 (11)0.0349 (11)
S10.04603 (16)−0.41163 (10)−0.10308 (4)0.0439 (4)
S2−0.89623 (17)−0.13257 (10)−0.17838 (4)0.0454 (4)
C1−0.3884 (6)−0.3352 (3)−0.20038 (12)0.0312 (13)
H1A−0.3736−0.3863−0.21380.037*
H1B−0.4851−0.3044−0.20670.037*
C2−0.5377 (6)−0.4218 (3)−0.16175 (12)0.0319 (13)
H2A−0.5197−0.4804−0.17060.038*
H2B−0.6343−0.3973−0.17080.038*
C3−0.5565 (6)−0.4290 (3)−0.12744 (13)0.0352 (14)
H3A−0.6493−0.4652−0.12250.042*
H3B−0.4628−0.4572−0.11850.042*
C4−0.5554 (7)−0.3370 (4)−0.08118 (12)0.0359 (14)
H4A−0.6343−0.3753−0.07150.043*
H4B−0.4504−0.3600−0.07590.043*
C5−0.4477 (7)−0.1893 (4)−0.07469 (13)0.0402 (15)
H5A−0.3462−0.2160−0.06900.048*
H5B−0.4639−0.1378−0.06150.048*
C6−0.3048 (6)−0.1014 (3)−0.11345 (14)0.0364 (14)
H6A−0.2068−0.1262−0.10500.044*
H6B−0.3220−0.0432−0.10420.044*
C7−0.2918 (6)−0.0930 (4)−0.14761 (14)0.0394 (15)
H7A−0.3886−0.0665−0.15590.047*
H7B−0.2024−0.0547−0.15290.047*
C8−0.2837 (6)−0.1871 (4)−0.19439 (14)0.0367 (14)
H8A−0.3902−0.1692−0.20080.044*
H8B−0.2067−0.1484−0.20450.044*
C9−0.1478 (6)−0.2927 (4)−0.22812 (13)0.0335 (13)
H9A−0.0605−0.2495−0.22610.040*
C10−0.0759 (6)−0.3830 (3)−0.22447 (12)0.0306 (12)
C110.0020 (6)−0.4024 (4)−0.19683 (13)0.0341 (13)
H11A0.0072−0.3594−0.18130.041*
C120.0705 (7)−0.4831 (4)−0.19227 (14)0.0420 (14)
H12A0.1230−0.4953−0.17370.050*
C130.0628 (7)−0.5459 (4)−0.21461 (15)0.0455 (16)
H13A0.1101−0.6013−0.21140.055*
C14−0.0131 (7)−0.5287 (4)−0.24141 (15)0.0467 (17)
H14A−0.0177−0.5725−0.25670.056*
C15−0.0835 (7)−0.4479 (4)−0.24657 (13)0.0383 (13)
H15A−0.1367−0.4372−0.26520.046*
C16−0.2242 (6)−0.2766 (4)−0.25908 (13)0.0438 (16)
H16A−0.2742−0.2190−0.25920.066*
H16B−0.3034−0.3217−0.26290.066*
H16C−0.1440−0.2790−0.27500.066*
C17−0.7257 (6)−0.2194 (4)−0.05969 (13)0.0384 (14)
H17A−0.7910−0.2728−0.05640.046*
C18−0.7153 (6)−0.1745 (4)−0.02895 (13)0.0363 (14)
C19−0.6286 (7)−0.2120 (4)−0.00594 (14)0.0474 (17)
H19A−0.5739−0.2649−0.00970.057*
C20−0.6200 (8)−0.1737 (5)0.02239 (15)0.0557 (18)
H20A−0.5632−0.20180.03820.067*
C21−0.6924 (9)−0.0955 (5)0.02797 (17)0.068 (2)
H21A−0.6834−0.06790.04720.082*
C22−0.7772 (11)−0.0585 (6)0.00542 (19)0.086 (3)
H22A−0.8288−0.00450.00900.104*
C23−0.7900 (9)−0.0976 (5)−0.02252 (16)0.065 (2)
H23−0.8523−0.0707−0.03780.078*
C24−0.8099 (7)−0.1669 (4)−0.08374 (14)0.0486 (17)
H24A−0.8077−0.1988−0.10310.073*
H24B−0.7578−0.1104−0.08620.073*
H24C−0.9189−0.1576−0.07750.073*
C25−0.1125 (6)−0.3557 (3)−0.11025 (12)0.0292 (12)
C26−0.7334 (6)−0.1772 (3)−0.16823 (12)0.0286 (12)
Ni2−0.09613 (7)−0.75727 (4)−0.112058 (15)0.02774 (16)
N9−0.1996 (6)−0.7839 (3)−0.18264 (10)0.0353 (11)
N10−0.0978 (5)−0.8651 (3)−0.14084 (10)0.0315 (10)
H10−0.1938−0.8931−0.13850.038*
N110.0348 (5)−0.8330 (3)−0.08278 (10)0.0340 (11)
H110.1397−0.8187−0.08570.041*
N120.0131 (5)−0.7279 (3)−0.04078 (11)0.0395 (12)
N13−0.1034 (5)−0.6485 (3)−0.08377 (10)0.0362 (11)
H13−0.0121−0.6166−0.08700.043*
N14−0.2280 (5)−0.6848 (3)−0.14172 (10)0.0286 (10)
H14−0.3312−0.7040−0.14020.034*
N15−0.3111 (5)−0.8075 (3)−0.09316 (12)0.0441 (13)
N160.1144 (5)−0.7100 (3)−0.13003 (11)0.0363 (11)
S3−0.57566 (18)−0.91335 (11)−0.09892 (4)0.0505 (4)
S40.38600 (18)−0.66232 (11)−0.16098 (4)0.0537 (5)
C27−0.0798 (6)−0.8436 (4)−0.17323 (12)0.0342 (13)
H27A0.0245−0.8171−0.17670.041*
H27B−0.0864−0.8977−0.18550.041*
C280.0249 (6)−0.9231 (4)−0.12818 (14)0.0388 (15)
H28A0.1298−0.9019−0.13440.047*
H28B0.0111−0.9831−0.13610.047*
C290.0124 (6)−0.9235 (3)−0.09346 (14)0.0388 (15)
H29A−0.0919−0.9454−0.08710.047*
H29B0.0936−0.9621−0.08460.047*
C30−0.0025 (7)−0.8179 (4)−0.05011 (13)0.0423 (15)
H30A−0.1114−0.8373−0.04620.051*
H30B0.0680−0.8544−0.03750.051*
C31−0.1116 (7)−0.6700 (4)−0.05131 (12)0.0398 (14)
H31A−0.1073−0.6151−0.03950.048*
H31B−0.2139−0.6980−0.04710.048*
C32−0.2367 (6)−0.5964 (4)−0.09557 (14)0.0399 (15)
H32A−0.2327−0.5362−0.08740.048*
H32B−0.3375−0.6233−0.08950.048*
C33−0.2220 (6)−0.5949 (4)−0.13008 (13)0.0355 (14)
H33A−0.3086−0.5602−0.13890.043*
H33B−0.1216−0.5673−0.13600.043*
C34−0.1791 (7)−0.6952 (4)−0.17348 (13)0.0369 (14)
H34A−0.2426−0.6565−0.18670.044*
H34B−0.0676−0.6783−0.17570.044*
C35−0.2490 (6)−0.8016 (4)−0.21473 (13)0.0380 (14)
H35−0.1526−0.8155−0.22670.046*
C36−0.3563 (6)−0.8813 (3)−0.21594 (13)0.0309 (13)
C37−0.3497 (6)−0.9361 (4)−0.24072 (13)0.0365 (14)
H37−0.2736−0.9264−0.25610.044*
C38−0.4543 (7)−1.0059 (4)−0.24333 (14)0.0435 (16)
H38−0.4500−1.0433−0.26050.052*
C39−0.5631 (7)−1.0203 (4)−0.22100 (15)0.0439 (15)
H39−0.6340−1.0679−0.22280.053*
C40−0.5708 (7)−0.9666 (3)−0.19603 (14)0.0398 (14)
H40−0.6474−0.9768−0.18080.048*
C41−0.4667 (6)−0.8977 (4)−0.19312 (13)0.0374 (14)
H41−0.4703−0.8615−0.17560.045*
C42−0.3315 (7)−0.7254 (4)−0.23042 (14)0.0487 (17)
H42A−0.2607−0.6751−0.23120.073*
H42B−0.4260−0.7097−0.21900.073*
H42C−0.3609−0.7425−0.25110.073*
C430.1719 (6)−0.6900 (4)−0.04258 (14)0.0384 (15)
H430.1953−0.6751−0.06420.046*
C440.1845 (7)−0.6076 (4)−0.02341 (13)0.0386 (14)
C450.2708 (9)−0.5376 (5)−0.03401 (16)0.064 (2)
H450.3126−0.5389−0.05400.077*
C460.2966 (11)−0.4656 (5)−0.01568 (19)0.086 (3)
H460.3594−0.4189−0.02300.103*
C470.2330 (6)−0.4605 (3)0.01289 (11)0.063 (2)
H470.2497−0.41070.02540.075*
C480.1452 (6)−0.5289 (3)0.02279 (11)0.0493 (17)
H480.0983−0.52580.04230.059*
C490.1221 (7)−0.6025 (4)0.00538 (14)0.0467 (16)
H490.0629−0.64990.01330.056*
C500.2954 (7)−0.7538 (5)−0.03109 (15)0.0561 (18)
H50A0.2973−0.8054−0.04420.084*
H50B0.2699−0.7714−0.01030.084*
H50C0.3985−0.7255−0.03140.084*
C51−0.4230 (7)−0.8509 (4)−0.09556 (13)0.0372 (13)
C520.2301 (6)−0.6896 (3)−0.14247 (13)0.0314 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0199 (3)0.0276 (3)0.0314 (4)0.0002 (3)−0.0008 (3)−0.0027 (3)
N10.025 (2)0.038 (3)0.034 (3)−0.008 (2)0.006 (2)−0.009 (2)
N20.026 (2)0.033 (2)0.032 (3)0.003 (2)0.003 (2)−0.005 (2)
N30.023 (2)0.028 (2)0.034 (3)−0.0013 (19)0.003 (2)−0.0027 (19)
N40.029 (2)0.045 (3)0.035 (3)0.007 (2)0.006 (2)−0.011 (2)
N50.026 (2)0.031 (2)0.043 (3)0.002 (2)0.003 (2)−0.010 (2)
N60.020 (2)0.026 (2)0.038 (3)−0.0015 (18)0.003 (2)0.000 (2)
N70.028 (2)0.045 (3)0.039 (3)0.004 (2)−0.003 (2)−0.002 (2)
N80.029 (2)0.036 (3)0.039 (3)−0.003 (2)0.000 (2)0.004 (2)
S10.0275 (7)0.0465 (9)0.0578 (11)0.0074 (6)−0.0065 (7)−0.0032 (8)
S20.0241 (7)0.0555 (10)0.0565 (11)0.0053 (7)−0.0048 (7)0.0050 (8)
C10.028 (3)0.035 (3)0.031 (3)−0.012 (2)0.001 (3)−0.006 (2)
C20.037 (3)0.023 (3)0.035 (3)−0.010 (2)0.001 (3)−0.009 (2)
C30.036 (3)0.023 (3)0.046 (4)−0.004 (2)0.014 (3)0.000 (2)
C40.037 (3)0.041 (3)0.030 (3)0.008 (3)0.003 (3)−0.002 (3)
C50.034 (3)0.049 (4)0.037 (4)−0.002 (3)0.001 (3)−0.021 (3)
C60.027 (3)0.025 (3)0.057 (4)−0.008 (2)−0.006 (3)−0.021 (3)
C70.030 (3)0.025 (3)0.064 (4)−0.002 (2)0.007 (3)−0.010 (3)
C80.027 (3)0.036 (3)0.047 (4)0.001 (2)0.002 (3)0.011 (3)
C90.029 (3)0.039 (3)0.033 (3)−0.002 (2)−0.002 (3)0.007 (3)
C100.026 (3)0.042 (3)0.024 (3)−0.004 (3)0.000 (3)0.002 (2)
C110.034 (3)0.041 (3)0.027 (3)−0.002 (3)−0.001 (3)−0.003 (3)
C120.035 (3)0.050 (4)0.041 (4)−0.003 (3)−0.001 (3)0.003 (3)
C130.039 (3)0.041 (3)0.056 (4)−0.004 (3)0.011 (3)0.006 (3)
C140.044 (4)0.046 (4)0.050 (5)−0.003 (3)0.004 (3)−0.013 (3)
C150.030 (3)0.052 (4)0.032 (3)−0.010 (3)0.000 (3)−0.006 (3)
C160.035 (3)0.059 (4)0.037 (4)0.011 (3)0.001 (3)0.006 (3)
C170.029 (3)0.049 (4)0.036 (3)0.002 (3)0.000 (3)0.001 (3)
C180.035 (3)0.041 (3)0.033 (3)−0.002 (3)0.009 (3)−0.008 (3)
C190.056 (4)0.048 (4)0.038 (4)0.009 (3)−0.008 (3)−0.010 (3)
C200.050 (4)0.077 (5)0.040 (4)0.005 (4)−0.010 (3)−0.007 (4)
C210.078 (5)0.084 (6)0.041 (4)0.005 (5)0.005 (4)−0.024 (4)
C220.114 (7)0.086 (6)0.058 (5)0.055 (6)−0.011 (5)−0.033 (5)
C230.079 (5)0.075 (5)0.040 (4)0.033 (4)−0.013 (4)−0.017 (4)
C240.042 (3)0.068 (5)0.035 (4)0.015 (3)−0.004 (3)−0.015 (3)
C250.028 (3)0.027 (3)0.032 (3)−0.002 (2)−0.005 (3)0.000 (2)
C260.028 (3)0.028 (3)0.030 (3)−0.003 (2)0.003 (2)−0.002 (2)
Ni20.0234 (3)0.0315 (4)0.0284 (4)−0.0006 (3)−0.0012 (3)−0.0009 (3)
N90.049 (3)0.034 (3)0.023 (3)0.002 (2)0.001 (2)−0.001 (2)
N100.029 (2)0.029 (2)0.037 (3)0.000 (2)−0.005 (2)−0.001 (2)
N110.024 (2)0.037 (3)0.041 (3)−0.0031 (19)−0.010 (2)−0.001 (2)
N120.038 (3)0.042 (3)0.038 (3)0.004 (2)−0.004 (2)−0.009 (2)
N130.032 (2)0.037 (3)0.040 (3)0.005 (2)−0.006 (2)−0.005 (2)
N140.027 (2)0.026 (2)0.033 (3)0.0014 (18)−0.007 (2)0.001 (2)
N150.030 (3)0.059 (3)0.043 (3)−0.008 (2)0.004 (2)0.001 (3)
N160.031 (2)0.039 (3)0.039 (3)−0.005 (2)0.002 (2)0.000 (2)
S30.0303 (8)0.0555 (10)0.0658 (12)−0.0068 (8)−0.0041 (8)−0.0032 (9)
S40.0299 (8)0.0550 (10)0.0761 (13)−0.0029 (7)0.0103 (8)0.0162 (9)
C270.029 (3)0.042 (3)0.032 (3)0.005 (3)−0.004 (3)−0.005 (3)
C280.034 (3)0.028 (3)0.054 (4)−0.001 (2)−0.006 (3)−0.009 (3)
C290.034 (3)0.028 (3)0.054 (4)−0.002 (2)−0.010 (3)0.004 (3)
C300.040 (3)0.053 (4)0.034 (4)−0.004 (3)0.001 (3)0.010 (3)
C310.040 (3)0.051 (4)0.029 (3)0.002 (3)0.001 (3)−0.005 (3)
C320.033 (3)0.039 (3)0.048 (4)0.012 (3)−0.008 (3)−0.014 (3)
C330.034 (3)0.035 (3)0.037 (4)0.004 (3)−0.005 (3)−0.001 (3)
C340.035 (3)0.047 (4)0.029 (3)−0.005 (3)−0.006 (3)0.000 (3)
C350.036 (3)0.052 (4)0.026 (3)−0.001 (3)−0.004 (3)−0.003 (3)
C360.028 (3)0.033 (3)0.032 (3)0.000 (2)−0.007 (3)0.005 (3)
C370.034 (3)0.045 (4)0.031 (3)0.001 (3)−0.003 (3)−0.003 (3)
C380.052 (4)0.037 (3)0.041 (4)0.009 (3)−0.016 (3)−0.004 (3)
C390.040 (3)0.035 (3)0.057 (4)0.001 (3)−0.013 (3)0.003 (3)
C400.035 (3)0.038 (3)0.046 (4)−0.008 (3)−0.001 (3)0.010 (3)
C410.040 (3)0.040 (3)0.032 (3)0.008 (3)0.003 (3)0.003 (3)
C420.061 (4)0.048 (4)0.036 (4)−0.019 (3)−0.017 (3)0.010 (3)
C430.034 (3)0.056 (4)0.024 (3)−0.002 (3)−0.003 (3)−0.005 (3)
C440.040 (3)0.048 (4)0.028 (3)0.005 (3)−0.005 (3)−0.004 (3)
C450.099 (6)0.057 (5)0.036 (4)−0.020 (4)0.021 (4)−0.002 (4)
C460.149 (8)0.053 (5)0.057 (5)−0.039 (5)0.031 (6)0.000 (4)
C470.087 (6)0.050 (4)0.051 (5)−0.006 (4)0.015 (4)−0.015 (4)
C480.059 (4)0.055 (4)0.034 (4)−0.006 (3)0.004 (3)−0.005 (3)
C490.048 (4)0.055 (4)0.037 (4)−0.014 (3)0.002 (3)−0.004 (3)
C500.046 (3)0.055 (4)0.067 (5)0.011 (4)−0.019 (3)−0.014 (4)
C510.030 (3)0.047 (3)0.035 (3)0.002 (3)0.000 (3)0.003 (3)
C520.028 (3)0.025 (3)0.042 (4)−0.001 (2)−0.003 (3)−0.001 (3)
Geometric parameters (Å, °) top
Ni1—N62.064 (4)Ni2—N142.049 (4)
Ni1—N32.068 (4)Ni2—N112.063 (4)
Ni1—N22.079 (4)Ni2—N132.080 (4)
Ni1—N52.086 (4)Ni2—N102.081 (4)
Ni1—N82.098 (5)Ni2—N162.092 (4)
Ni1—N72.126 (5)Ni2—N152.156 (5)
N1—C11.446 (6)N9—C341.429 (7)
N1—C81.449 (7)N9—C271.432 (7)
N1—C91.460 (7)N9—C351.498 (7)
N2—C11.473 (6)N10—C271.471 (7)
N2—C21.484 (6)N10—C281.482 (7)
N2—H20.9300N10—H100.9300
N3—C31.459 (6)N11—C291.476 (7)
N3—C41.496 (6)N11—C301.491 (7)
N3—H30.9300N11—H110.9300
N4—C41.426 (7)N12—C301.446 (7)
N4—C51.436 (7)N12—C311.460 (7)
N4—C171.468 (6)N12—C431.475 (7)
N5—C61.477 (6)N13—C311.467 (7)
N5—C51.479 (7)N13—C321.484 (7)
N5—H50.9300N13—H130.9300
N6—C71.473 (7)N14—C341.467 (7)
N6—C81.484 (7)N14—C331.470 (7)
N6—H60.9300N14—H140.9300
N7—C251.160 (6)N15—C511.168 (7)
N8—C261.167 (6)N16—C521.171 (6)
S1—C251.632 (5)S3—C511.623 (6)
S2—C261.611 (6)S4—C521.615 (6)
C1—H1A0.9900C27—H27A0.9900
C1—H1B0.9900C27—H27B0.9900
C2—C31.522 (7)C28—C291.531 (8)
C2—H2A0.9900C28—H28A0.9900
C2—H2B0.9900C28—H28B0.9900
C3—H3A0.9900C29—H29A0.9900
C3—H3B0.9900C29—H29B0.9900
C4—H4A0.9900C30—H30A0.9900
C4—H4B0.9900C30—H30B0.9900
C5—H5A0.9900C31—H31A0.9900
C5—H5B0.9900C31—H31B0.9900
C6—C71.513 (8)C32—C331.524 (8)
C6—H6A0.9900C32—H32A0.9900
C6—H6B0.9900C32—H32B0.9900
C7—H7A0.9900C33—H33A0.9900
C7—H7B0.9900C33—H33B0.9900
C8—H8A0.9900C34—H34A0.9900
C8—H8B0.9900C34—H34B0.9900
C9—C101.521 (8)C35—C361.527 (8)
C9—C161.530 (7)C35—C421.528 (8)
C9—H9A1.0000C35—H351.0000
C10—C151.393 (7)C36—C371.377 (8)
C10—C111.418 (7)C36—C411.399 (7)
C11—C121.382 (8)C37—C381.397 (8)
C11—H11A0.9500C37—H370.9500
C12—C131.377 (8)C38—C391.370 (8)
C12—H12A0.9500C38—H380.9500
C13—C141.370 (9)C39—C401.374 (8)
C13—H13A0.9500C39—H390.9500
C14—C151.394 (8)C40—C411.385 (7)
C14—H14A0.9500C40—H400.9500
C15—H15A0.9500C41—H410.9500
C16—H16A0.9800C42—H42A0.9800
C16—H16B0.9800C42—H42B0.9800
C16—H16C0.9800C42—H42C0.9800
C17—C241.511 (8)C43—C441.523 (8)
C17—C181.521 (8)C43—C501.523 (8)
C17—H17A1.0000C43—H431.0000
C18—C231.368 (9)C44—C491.376 (8)
C18—C191.379 (8)C44—C451.381 (9)
C19—C201.380 (8)C45—C461.383 (10)
C19—H19A0.9500C45—H450.9500
C20—C211.369 (9)C46—C471.371 (9)
C20—H20A0.9500C46—H460.9500
C21—C221.352 (10)C47—C481.3592
C21—H21A0.9500C47—H470.9500
C22—C231.372 (10)C48—C491.377
C22—H22A0.9500C48—H480.9500
C23—H230.9500C49—H490.9500
C24—H24A0.9800C50—H50A0.9800
C24—H24B0.9800C50—H50B0.9800
C24—H24C0.9800C50—H50C0.9800
N6—Ni1—N3179.51 (18)N14—Ni2—N11178.53 (18)
N6—Ni1—N295.11 (17)N14—Ni2—N1386.07 (17)
N3—Ni1—N285.24 (16)N11—Ni2—N1395.32 (18)
N6—Ni1—N585.33 (17)N14—Ni2—N1092.18 (17)
N3—Ni1—N594.32 (16)N11—Ni2—N1086.42 (17)
N2—Ni1—N5178.97 (18)N13—Ni2—N10177.78 (18)
N6—Ni1—N891.56 (17)N14—Ni2—N1692.49 (18)
N3—Ni1—N888.08 (17)N11—Ni2—N1688.03 (17)
N2—Ni1—N892.18 (18)N13—Ni2—N1688.56 (18)
N5—Ni1—N888.74 (18)N10—Ni2—N1692.88 (18)
N6—Ni1—N788.78 (17)N14—Ni2—N1588.38 (18)
N3—Ni1—N791.58 (17)N11—Ni2—N1591.09 (19)
N2—Ni1—N787.14 (18)N13—Ni2—N1591.70 (19)
N5—Ni1—N791.94 (18)N10—Ni2—N1586.89 (19)
N8—Ni1—N7179.3 (2)N16—Ni2—N15179.1 (2)
C1—N1—C8115.7 (4)C34—N9—C27116.0 (5)
C1—N1—C9116.7 (4)C34—N9—C35118.1 (4)
C8—N1—C9117.1 (4)C27—N9—C35111.0 (4)
C1—N2—C2115.8 (4)C27—N10—C28115.1 (4)
C1—N2—Ni1113.2 (3)C27—N10—Ni2114.3 (3)
C2—N2—Ni1105.1 (3)C28—N10—Ni2104.0 (3)
C1—N2—H2107.5C27—N10—H10107.7
C2—N2—H2107.5C28—N10—H10107.7
Ni1—N2—H2107.5Ni2—N10—H10107.7
C3—N3—C4113.8 (4)C29—N11—C30115.2 (5)
C3—N3—Ni1106.7 (3)C29—N11—Ni2105.0 (3)
C4—N3—Ni1112.6 (3)C30—N11—Ni2113.5 (3)
C3—N3—H3107.8C29—N11—H11107.6
C4—N3—H3107.8C30—N11—H11107.6
Ni1—N3—H3107.8Ni2—N11—H11107.6
C4—N4—C5118.4 (4)C30—N12—C31114.9 (5)
C4—N4—C17119.4 (5)C30—N12—C43116.4 (5)
C5—N4—C17119.2 (5)C31—N12—C43114.5 (5)
C6—N5—C5114.9 (4)C31—N13—C32115.1 (4)
C6—N5—Ni1105.2 (3)C31—N13—Ni2113.8 (3)
C5—N5—Ni1113.6 (3)C32—N13—Ni2104.2 (3)
C6—N5—H5107.6C31—N13—H13107.8
C5—N5—H5107.6C32—N13—H13107.8
Ni1—N5—H5107.6Ni2—N13—H13107.8
C7—N6—C8116.5 (4)C34—N14—C33115.0 (4)
C7—N6—Ni1105.4 (3)C34—N14—Ni2113.1 (3)
C8—N6—Ni1112.8 (3)C33—N14—Ni2105.4 (3)
C7—N6—H6107.2C34—N14—H14107.7
C8—N6—H6107.2C33—N14—H14107.7
Ni1—N6—H6107.2Ni2—N14—H14107.7
C25—N7—Ni1160.6 (5)C51—N15—Ni2149.8 (5)
C26—N8—Ni1166.6 (4)C52—N16—Ni2173.1 (5)
N1—C1—N2108.7 (4)N9—C27—N10110.4 (4)
N1—C1—H1A110.0N9—C27—H27A109.6
N2—C1—H1A110.0N10—C27—H27A109.6
N1—C1—H1B110.0N9—C27—H27B109.6
N2—C1—H1B110.0N10—C27—H27B109.6
H1A—C1—H1B108.3H27A—C27—H27B108.1
N2—C2—C3109.0 (4)N10—C28—C29109.2 (4)
N2—C2—H2A109.9N10—C28—H28A109.8
C3—C2—H2A109.9C29—C28—H28A109.8
N2—C2—H2B109.9N10—C28—H28B109.8
C3—C2—H2B109.9C29—C28—H28B109.8
H2A—C2—H2B108.3H28A—C28—H28B108.3
N3—C3—C2108.7 (4)N11—C29—C28107.7 (4)
N3—C3—H3A110.0N11—C29—H29A110.2
C2—C3—H3A110.0C28—C29—H29A110.2
N3—C3—H3B110.0N11—C29—H29B110.2
C2—C3—H3B110.0C28—C29—H29B110.2
H3A—C3—H3B108.3H29A—C29—H29B108.5
N4—C4—N3114.0 (4)N12—C30—N11113.7 (5)
N4—C4—H4A108.8N12—C30—H30A108.8
N3—C4—H4A108.8N11—C30—H30A108.8
N4—C4—H4B108.8N12—C30—H30B108.8
N3—C4—H4B108.8N11—C30—H30B108.8
H4A—C4—H4B107.6H30A—C30—H30B107.7
N4—C5—N5114.3 (4)N12—C31—N13114.2 (5)
N4—C5—H5A108.7N12—C31—H31A108.7
N5—C5—H5A108.7N13—C31—H31A108.7
N4—C5—H5B108.7N12—C31—H31B108.7
N5—C5—H5B108.7N13—C31—H31B108.7
H5A—C5—H5B107.6H31A—C31—H31B107.6
N5—C6—C7108.1 (4)N13—C32—C33107.1 (4)
N5—C6—H6A110.1N13—C32—H32A110.3
C7—C6—H6A110.1C33—C32—H32A110.3
N5—C6—H6B110.1N13—C32—H32B110.3
C7—C6—H6B110.1C33—C32—H32B110.3
H6A—C6—H6B108.4H32A—C32—H32B108.6
N6—C7—C6109.1 (5)N14—C33—C32109.3 (5)
N6—C7—H7A109.9N14—C33—H33A109.8
C6—C7—H7A109.9C32—C33—H33A109.8
N6—C7—H7B109.9N14—C33—H33B109.8
C6—C7—H7B109.9C32—C33—H33B109.8
H7A—C7—H7B108.3H33A—C33—H33B108.3
N1—C8—N6107.9 (4)N9—C34—N14109.7 (5)
N1—C8—H8A110.1N9—C34—H34A109.7
N6—C8—H8A110.1N14—C34—H34A109.7
N1—C8—H8B110.1N9—C34—H34B109.7
N6—C8—H8B110.1N14—C34—H34B109.7
H8A—C8—H8B108.4H34A—C34—H34B108.2
N1—C9—C10108.7 (4)N9—C35—C36110.2 (5)
N1—C9—C16112.6 (4)N9—C35—C42114.7 (5)
C10—C9—C16114.3 (5)C36—C35—C42108.6 (4)
N1—C9—H9A106.9N9—C35—H35107.7
C10—C9—H9A106.9C36—C35—H35107.7
C16—C9—H9A106.9C42—C35—H35107.7
C15—C10—C11118.1 (5)C37—C36—C41119.1 (5)
C15—C10—C9123.8 (5)C37—C36—C35119.4 (5)
C11—C10—C9118.0 (5)C41—C36—C35121.5 (5)
C12—C11—C10120.7 (5)C36—C37—C38120.3 (6)
C12—C11—H11A119.7C36—C37—H37119.8
C10—C11—H11A119.7C38—C37—H37119.8
C13—C12—C11120.1 (6)C39—C38—C37119.8 (6)
C13—C12—H12A120.0C39—C38—H38120.1
C11—C12—H12A120.0C37—C38—H38120.1
C14—C13—C12120.2 (6)C38—C39—C40120.6 (6)
C14—C13—H13A119.9C38—C39—H39119.7
C12—C13—H13A119.9C40—C39—H39119.7
C13—C14—C15120.9 (6)C39—C40—C41120.0 (6)
C13—C14—H14A119.5C39—C40—H40120.0
C15—C14—H14A119.5C41—C40—H40120.0
C10—C15—C14120.0 (5)C40—C41—C36120.1 (6)
C10—C15—H15A120.0C40—C41—H41119.9
C14—C15—H15A120.0C36—C41—H41119.9
C9—C16—H16A109.5C35—C42—H42A109.5
C9—C16—H16B109.5C35—C42—H42B109.5
H16A—C16—H16B109.5H42A—C42—H42B109.5
C9—C16—H16C109.5C35—C42—H42C109.5
H16A—C16—H16C109.5H42A—C42—H42C109.5
H16B—C16—H16C109.5H42B—C42—H42C109.5
N4—C17—C24114.3 (5)N12—C43—C44111.2 (5)
N4—C17—C18110.1 (4)N12—C43—C50111.5 (5)
C24—C17—C18114.2 (5)C44—C43—C50107.4 (5)
N4—C17—H17A105.8N12—C43—H43108.9
C24—C17—H17A105.8C44—C43—H43108.9
C18—C17—H17A105.8C50—C43—H43108.9
C23—C18—C19117.2 (6)C49—C44—C45118.2 (6)
C23—C18—C17123.1 (6)C49—C44—C43121.9 (6)
C19—C18—C17119.7 (5)C45—C44—C43119.6 (6)
C18—C19—C20121.0 (6)C44—C45—C46120.4 (6)
C18—C19—H19A119.5C44—C45—H45119.8
C20—C19—H19A119.5C46—C45—H45119.8
C21—C20—C19120.6 (6)C47—C46—C45121.2 (7)
C21—C20—H20A119.7C47—C46—H46119.4
C19—C20—H20A119.7C45—C46—H46119.4
C22—C21—C20118.4 (7)C48—C47—C46117.9
C22—C21—H21A120.8C48—C47—H47121.1
C20—C21—H21A120.8C46—C47—H47121.1
C21—C22—C23121.2 (7)C47—C48—C49122.1
C21—C22—H22A119.4C47—C48—H48119.0
C23—C22—H22A119.4C49—C48—H48119.0
C18—C23—C22121.6 (7)C44—C49—C48120.2
C18—C23—H23119.2C44—C49—H49119.9
C22—C23—H23119.2C48—C49—H49119.9
C17—C24—H24A109.5C43—C50—H50A109.5
C17—C24—H24B109.5C43—C50—H50B109.5
H24A—C24—H24B109.5H50A—C50—H50B109.5
C17—C24—H24C109.5C43—C50—H50C109.5
H24A—C24—H24C109.5H50A—C50—H50C109.5
H24B—C24—H24C109.5H50B—C50—H50C109.5
N7—C25—S1178.6 (5)N15—C51—S3178.5 (6)
N8—C26—S2179.0 (6)N16—C52—S4177.5 (5)
N6—Ni1—N2—C1−36.9 (4)C17—C18—C19—C20−178.5 (6)
N3—Ni1—N2—C1142.8 (3)C17—C18—C23—C22−179.6 (7)
N8—Ni1—N2—C154.9 (3)N14—Ni2—N10—C2740.1 (4)
N7—Ni1—N2—C1−125.4 (4)N11—Ni2—N10—C27−140.3 (4)
N6—Ni1—N2—C2−164.1 (3)N16—Ni2—N10—C27−52.5 (4)
N3—Ni1—N2—C215.5 (3)N15—Ni2—N10—C27128.4 (4)
N8—Ni1—N2—C2−72.4 (3)N14—Ni2—N10—C28166.5 (3)
N7—Ni1—N2—C2107.4 (3)N11—Ni2—N10—C28−14.0 (3)
N2—Ni1—N3—C314.0 (3)N16—Ni2—N10—C2873.9 (3)
N5—Ni1—N3—C3−165.1 (3)N15—Ni2—N10—C28−105.3 (3)
N8—Ni1—N3—C3106.3 (4)N13—Ni2—N11—C29162.0 (3)
N7—Ni1—N3—C3−73.0 (3)N10—Ni2—N11—C29−16.6 (3)
N2—Ni1—N3—C4139.6 (3)N16—Ni2—N11—C29−109.7 (4)
N5—Ni1—N3—C4−39.5 (3)N15—Ni2—N11—C2970.2 (4)
N8—Ni1—N3—C4−128.1 (3)N13—Ni2—N11—C3035.3 (4)
N7—Ni1—N3—C452.6 (3)N10—Ni2—N11—C30−143.3 (4)
N6—Ni1—N5—C6−15.2 (3)N16—Ni2—N11—C30123.7 (4)
N3—Ni1—N5—C6165.2 (3)N15—Ni2—N11—C30−56.5 (4)
N8—Ni1—N5—C6−106.9 (3)N14—Ni2—N13—C31144.5 (4)
N7—Ni1—N5—C673.4 (4)N11—Ni2—N13—C31−35.0 (4)
N6—Ni1—N5—C5−141.7 (4)N16—Ni2—N13—C31−122.9 (4)
N3—Ni1—N5—C538.6 (4)N15—Ni2—N13—C3156.2 (4)
N8—Ni1—N5—C5126.6 (4)N14—Ni2—N13—C3218.3 (3)
N7—Ni1—N5—C5−53.1 (4)N11—Ni2—N13—C32−161.2 (3)
N2—Ni1—N6—C7166.0 (3)N16—Ni2—N13—C32110.9 (4)
N5—Ni1—N6—C7−15.0 (3)N15—Ni2—N13—C32−69.9 (4)
N8—Ni1—N6—C773.6 (3)N13—Ni2—N14—C34138.9 (4)
N7—Ni1—N6—C7−107.0 (4)N10—Ni2—N14—C34−42.4 (4)
N2—Ni1—N6—C837.9 (4)N16—Ni2—N14—C3450.5 (4)
N5—Ni1—N6—C8−143.1 (4)N15—Ni2—N14—C34−129.3 (4)
N8—Ni1—N6—C8−54.5 (4)N13—Ni2—N14—C3312.4 (3)
N7—Ni1—N6—C8124.9 (4)N10—Ni2—N14—C33−168.9 (3)
N2—Ni1—N7—C2525.3 (13)N16—Ni2—N14—C33−76.0 (3)
N5—Ni1—N7—C25−155.2 (13)N15—Ni2—N14—C33104.2 (3)
N6—Ni1—N8—C26−129.0 (18)N14—Ni2—N15—C5169.8 (9)
N3—Ni1—N8—C2650.7 (18)N11—Ni2—N15—C51−108.9 (9)
N2—Ni1—N8—C26135.8 (18)N13—Ni2—N15—C51155.8 (9)
N5—Ni1—N8—C26−43.7 (18)N10—Ni2—N15—C51−22.5 (9)
C8—N1—C1—N2−82.6 (6)C34—N9—C27—N1076.2 (6)
C9—N1—C1—N2133.4 (5)C35—N9—C27—N10−145.2 (4)
C2—N2—C1—N1177.8 (4)C28—N10—C27—N9−177.0 (4)
Ni1—N2—C1—N156.3 (5)Ni2—N10—C27—N9−56.7 (5)
C1—N2—C2—C3−167.5 (4)C27—N10—C28—C29167.7 (4)
Ni1—N2—C2—C3−41.8 (5)Ni2—N10—C28—C2941.9 (5)
C4—N3—C3—C2−165.5 (4)C30—N11—C29—C28169.2 (4)
Ni1—N3—C3—C2−40.6 (5)Ni2—N11—C29—C2843.6 (5)
N2—C2—C3—N357.1 (6)N10—C28—C29—N11−59.9 (5)
C5—N4—C4—N3−71.6 (6)C31—N12—C30—N1174.2 (6)
C17—N4—C4—N388.8 (6)C43—N12—C30—N11−63.5 (7)
C3—N3—C4—N4178.6 (4)C29—N11—C30—N12−177.1 (4)
Ni1—N3—C4—N456.9 (5)Ni2—N11—C30—N12−56.0 (6)
C4—N4—C5—N569.9 (6)C30—N12—C31—N13−73.8 (6)
C17—N4—C5—N5−90.6 (6)C43—N12—C31—N1364.8 (6)
C6—N5—C5—N4−175.2 (4)C32—N13—C31—N12174.8 (4)
Ni1—N5—C5—N4−54.0 (5)Ni2—N13—C31—N1254.6 (6)
C5—N5—C6—C7167.9 (4)C31—N13—C32—C33−170.1 (5)
Ni1—N5—C6—C742.2 (5)Ni2—N13—C32—C33−44.7 (5)
C8—N6—C7—C6168.6 (4)C34—N14—C33—C32−166.4 (4)
Ni1—N6—C7—C642.7 (5)Ni2—N14—C33—C32−41.1 (5)
N5—C6—C7—N6−59.0 (5)N13—C32—C33—N1459.9 (6)
C1—N1—C8—N683.6 (6)C27—N9—C34—N14−79.7 (6)
C9—N1—C8—N6−132.5 (4)C35—N9—C34—N14144.8 (4)
C7—N6—C8—N1179.5 (4)C33—N14—C34—N9−176.3 (4)
Ni1—N6—C8—N1−58.4 (5)Ni2—N14—C34—N962.5 (5)
C1—N1—C9—C10−62.3 (6)C34—N9—C35—C36−145.4 (5)
C8—N1—C9—C10154.2 (5)C27—N9—C35—C3677.0 (5)
C1—N1—C9—C1665.5 (6)C34—N9—C35—C42−22.5 (7)
C8—N1—C9—C16−78.0 (6)C27—N9—C35—C42−160.0 (5)
N1—C9—C10—C15124.0 (5)N9—C35—C36—C37−145.6 (5)
C16—C9—C10—C15−2.8 (8)C42—C35—C36—C3787.9 (6)
N1—C9—C10—C11−55.3 (6)N9—C35—C36—C4137.5 (7)
C16—C9—C10—C11177.9 (5)C42—C35—C36—C41−88.9 (6)
C15—C10—C11—C121.0 (8)C35—C36—C37—C38−175.5 (5)
C9—C10—C11—C12−179.6 (5)C36—C37—C38—C39−0.5 (8)
C10—C11—C12—C13−0.4 (8)C37—C38—C39—C400.2 (8)
C11—C12—C13—C14−0.2 (9)C38—C39—C40—C41−0.7 (9)
C12—C13—C14—C150.0 (9)C39—C40—C41—C361.6 (8)
C11—C10—C15—C14−1.2 (8)C37—C36—C41—C40−2.0 (8)
C9—C10—C15—C14179.5 (5)C35—C36—C41—C40174.9 (5)
C13—C14—C15—C100.7 (9)C30—N12—C43—C44−162.1 (5)
C4—N4—C17—C24−94.8 (6)C31—N12—C43—C4459.9 (6)
C5—N4—C17—C2465.5 (7)C30—N12—C43—C50−42.4 (7)
C4—N4—C17—C18135.1 (5)C31—N12—C43—C50179.7 (5)
C5—N4—C17—C18−64.6 (7)N12—C43—C44—C4943.5 (8)
N4—C17—C18—C23137.0 (6)C50—C43—C44—C49−78.6 (7)
C24—C17—C18—C236.8 (9)N12—C43—C44—C45−141.4 (6)
N4—C17—C18—C19−43.7 (7)C50—C43—C44—C4596.5 (7)
C24—C17—C18—C19−173.9 (5)C43—C44—C45—C46−173.5 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3···S1i0.932.823.439 (4)125
N6—H6···S2ii0.932.713.347 (4)127
N11—H11···S3ii0.932.893.614 (5)136
N14—H14···S4i0.932.663.418 (4)139
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3···S1i0.932.823.439 (4)125
N6—H6···S2ii0.932.713.347 (4)127
N11—H11···S3ii0.932.893.614 (5)136
N14—H14···S4i0.932.663.418 (4)139
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.
Acknowledgements top

This work was partially supported by the Korea Research Foundation Grant funded by the Korean government (MOEHRD, Basic Research Promotion Fund; grant No. KRF-2007-331-C00144). The authors acknowledge the Korea Basic Science Institute for the X-ray data collections.

references
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