organic compounds
N,N,N′,N′-Tetramethyl-N′′-[2-(trimethylazaniumyl)ethyl]guanidinium bis(tetraphenylborate) acetone disolvate
aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
*Correspondence e-mail: willi.kantlehner@hs-aalen.de
The 10H26N42+·2C24H20B−·2C3H6O, comprises one cation, two tetraphenylborate ions and two acetone solvent molecules. The N and methyl C atoms of the terminal trimethylammonium group are disordered over two sets of sites, with a refined occupancy ratio of 0.846 (3):0.154 (3). The C—N bond lengths in the central C3N unit of the guanidinium ion range between 1.3308 (16) and 1.3508 (16) Å, indicating a degree of double-bond character. The central C atom is bonded to the three N atoms in a nearly ideal trigonal–planar geometry and the positive charge is delocalized in the CN3 plane. The C—N bond lengths in the terminal trimethylammonium group have values close to that of a typical single bond, and the second positive charge is localized there. In the crystal, the guanidinium ion is connected by N—H⋯O and C—H⋯O hydrogen bonds with the acetone molecules. C—H⋯π interactions are present between the guanidinium H atoms and the phenyl rings of the tetraphenylborate ions, leading to the formation of a two-dimensional supramolecular pattern along the bc plane.
of the title solvated salt, CKeywords: crystal structure; guanidinium salt; tetraphenylborate; hydrogen bonds.
CCDC reference: 1448754
Structure description
ω-Aminoalkylguanidines like N′′-[2-(dimethylamino)ethyl]- N,N,N′,N′-tetramethylguanidine (Tiritiris & Kantlehner, 2012) and its corresponding imine-nitrogen atom protonated guanidinium salts are well known in the literature (tetraphenylborate salt: Tiritiris & Kantlehner, 2012; bicarbonate salt: Tiritiris et al., 2011). Electrophiles can attack on the nitrogen atom of the (dimethylamino)ethyl group in these salts. By alkylation of the chloride salt with one equivalent of dimethyl sulfate and after with sodium tetraphenylborate, the here-presented crystalline title compound emerged. The of the structure comprises one cation, two tetraphenylborate ions and two acetone molecules (Fig. 1). The nitrogen and the methyl carbon atoms of the terminal trimethylammonium group are disordered over two sets of sites with a refined occupancy ratio of 0.846 (3):0.154 (3) (Fig. 2). Prominent bond parameters in the guanidinium ion are: C1—N1 = 1.3308 (16) Å, C1—N2 = 1.3425 (16) Å and C1—N3 = 1.3508 (16) Å, indicating partial double-bond character for all. The N—C1—N angles range from 118.36 (12) to 121.02 (11)°, indicating that the carbon centre C1 adopts a nearly ideal trigonal-planar environment. One of the two positive charges is completely delocalized in the CN3 plane, while the second positive charge is localized at the terminal trimethylammonium group. The N—C bond lengths in the [NMe3]+ group have values close to a typical single bond [d(N—C) = 1.464 (17)–1.55 (3) Å].
The C—N and C—C bond lengths in the dication are in very good agreement with the values obtained for N,N,N′,N′-tetramethyl-N′′-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate) acetone disolvate (Tiritiris, 2013b). The bond lengths and angles in both tetraphenylborate ions are in good agreement with the data from the analysis of the alkali metal tetraphenylborates (Behrens et al., 2012a).
In the crystal, the guanidinium ion is connected by N—H⋯O and C—H⋯O hydrogen bonds (Fig. 3) with the acetone molecules (Table 1). C—H⋯π interactions between the hydrogen atoms of –N(CH3) groups of the guanidinium ion and the phenyl carbon atoms of the tetraphenylborate ions are present (Table 1). This leads to the formation of a two-dimensional supramolecular pattern along the ac plane (Fig. 4). Such C—H⋯π interactions have been also observed in N-[3-(benzyldimethylazaniumyl)propyl]-N′,N′,N′′,N′′-tetramethylguanidinium bis(tetraphenylborate) (Tiritiris, 2013a) and N,N,N′,N′-tetramethyl-N′′-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate) acetone disolvate (Tiritiris, 2013b).
Synthesis and crystallization
The title compound was obtained by reaction of N,N,N′,N′-tetramethyl-N′′-[2-(dimethylamino)ethyl]guanidinium chloride (Tiritiris & Kantlehner, 2012) with one equivalent of dimethyl sulfate in acetonitrile at room temperature. After evaporation of the solvent, the crude N,N,N′,N′-tetramethyl-N′′-[2-(trimethylazaniumyl)ethyl]guanidinium chloride methyl sulfate (I) was washed with diethyl ether and dried in vacuo. 1.00 g (2.87 mmol) of (I) was dissolved in 20 ml acetonitrile and 1.96 g (5.74 mmol) of sodium tetraphenylborate in 20 ml acetonitrile was added. After stirring for one h at room temperature, the precipitated sodium chloride and sodium methyl sulfate was filtered off. The title compound crystallized from a saturated acetone solution after several weeks at 273 K, forming colorless single crystals. Yield: 2.18 g (88%).
Dimethyl sulfate is carcinogenic, mutagenic and highly poisonous. During the use appropriate precautions must be taken.
Refinement
Crystal data, data collection and structure . The The atoms N4, C8, C9 and C10 of the [NMe3]+ group are disordered over two sets of sites [N4A/N4B, C8A/C8B, C9A/C9B and C10A/C10B] with a refined occupancy ratio of 0.846 (3):0.154 (3). The two moieties were constrained to have similar geometries, and the anisotropic displacement parameters of equivalent atoms were constrained to be identical.
details are summarized in Table 2
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Structural data
CCDC reference: 1448754
https://doi.org/10.1107/S2414314616001292/zl4003sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616001292/zl4003Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616001292/zl4003Isup3.cml
Data collection: COLLECT (Hooft, 2004); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).C10H26N42+·2C24H20B−·2C3H6O | Z = 2 |
Mr = 956.92 | F(000) = 1032 |
Triclinic, P1 | Dx = 1.168 Mg m−3 |
a = 11.4419 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.1461 (5) Å | Cell parameters from 11355 reflections |
c = 18.8503 (9) Å | θ = 0.4–28.3° |
α = 110.6352 (13)° | µ = 0.07 mm−1 |
β = 101.824 (1)° | T = 100 K |
γ = 97.8879 (8)° | Block, colorless |
V = 2720.70 (18) Å3 | 0.33 × 0.24 × 0.13 mm |
Bruker–Nonius KappaCCD diffractometer | 10609 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 28.3°, θmin = 1.2° |
φ scans, and ω scans | h = −15→15 |
22310 measured reflections | k = −16→18 |
13295 independent reflections | l = −24→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: mixed |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0705P)2 + 1.2222P] where P = (Fo2 + 2Fc2)/3 |
13295 reflections | (Δ/σ)max < 0.001 |
680 parameters | Δρmax = 0.58 e Å−3 |
6 restraints | Δρmin = −0.32 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.59093 (10) | 0.41666 (8) | 0.31479 (6) | 0.0158 (2) | |
N2 | 0.75655 (10) | 0.34377 (8) | 0.34002 (6) | 0.0160 (2) | |
N3 | 0.56432 (10) | 0.26444 (9) | 0.33777 (7) | 0.0160 (2) | |
H3 | 0.5979 (17) | 0.2332 (14) | 0.3649 (11) | 0.030 (5)* | |
C1 | 0.63681 (11) | 0.34267 (10) | 0.33081 (7) | 0.0142 (2) | |
C2 | 0.48354 (12) | 0.44848 (11) | 0.33871 (8) | 0.0182 (3) | |
H2A | 0.4108 | 0.4169 | 0.2933 | 0.027* | |
H2B | 0.4971 | 0.5242 | 0.3582 | 0.027* | |
H2C | 0.4710 | 0.4256 | 0.3806 | 0.027* | |
C3 | 0.64100 (13) | 0.46827 (11) | 0.26869 (8) | 0.0212 (3) | |
H3A | 0.6852 | 0.5396 | 0.3035 | 0.032* | |
H3B | 0.5738 | 0.4694 | 0.2276 | 0.032* | |
H3C | 0.6975 | 0.4303 | 0.2443 | 0.032* | |
C4 | 0.85097 (12) | 0.44027 (11) | 0.37520 (8) | 0.0213 (3) | |
H4A | 0.8133 | 0.4991 | 0.3947 | 0.032* | |
H4B | 0.8905 | 0.4479 | 0.3354 | 0.032* | |
H4C | 0.9125 | 0.4386 | 0.4191 | 0.032* | |
C5 | 0.80177 (13) | 0.24885 (11) | 0.32670 (9) | 0.0232 (3) | |
H5A | 0.8248 | 0.2398 | 0.3765 | 0.035* | |
H5B | 0.8736 | 0.2540 | 0.3063 | 0.035* | |
H5C | 0.7372 | 0.1892 | 0.2883 | 0.035* | |
C6 | 0.43715 (11) | 0.21537 (10) | 0.29157 (7) | 0.0170 (3) | |
H6A | 0.3835 | 0.2625 | 0.3101 | 0.020* | |
H6B | 0.4105 | 0.1506 | 0.2989 | 0.020* | |
C7 | 0.42530 (12) | 0.19057 (11) | 0.20429 (8) | 0.0208 (3) | |
H7A | 0.4279 | 0.2558 | 0.1955 | 0.025* | |
H7B | 0.4971 | 0.1640 | 0.1911 | 0.025* | |
N4A | 0.3105 (4) | 0.1127 (3) | 0.1488 (2) | 0.0178 (4) | 0.846 (3) |
C8A | 0.19893 (18) | 0.1358 (2) | 0.17388 (14) | 0.0382 (6) | 0.846 (3) |
H8A1 | 0.2064 | 0.1348 | 0.2263 | 0.057* | 0.846 (3) |
H8A2 | 0.1265 | 0.0833 | 0.1362 | 0.057* | 0.846 (3) |
H8A3 | 0.1903 | 0.2045 | 0.1756 | 0.057* | 0.846 (3) |
C9A | 0.29953 (19) | 0.11284 (18) | 0.06795 (11) | 0.0304 (5) | 0.846 (3) |
H9A1 | 0.2325 | 0.0554 | 0.0295 | 0.046* | 0.846 (3) |
H9A2 | 0.3766 | 0.1045 | 0.0541 | 0.046* | 0.846 (3) |
H9A3 | 0.2824 | 0.1787 | 0.0676 | 0.046* | 0.846 (3) |
C10A | 0.32390 (19) | 0.00665 (14) | 0.14393 (12) | 0.0330 (5) | 0.846 (3) |
H10A | 0.3262 | 0.0024 | 0.1949 | 0.049* | 0.846 (3) |
H10B | 0.4002 | −0.0059 | 0.1304 | 0.049* | 0.846 (3) |
H10C | 0.2541 | −0.0457 | 0.1033 | 0.049* | 0.846 (3) |
N4B | 0.299 (2) | 0.1157 (16) | 0.1554 (13) | 0.0178 (4) | 0.154 (3) |
C8B | 0.2084 (11) | 0.1796 (11) | 0.1593 (8) | 0.0382 (6) | 0.154 (3) |
H8B1 | 0.2325 | 0.2345 | 0.1412 | 0.057* | 0.154 (3) |
H8B2 | 0.2040 | 0.2109 | 0.2138 | 0.057* | 0.154 (3) |
H8B3 | 0.1279 | 0.1361 | 0.1255 | 0.057* | 0.154 (3) |
C9B | 0.3109 (11) | 0.0687 (10) | 0.0737 (6) | 0.0304 (5) | 0.154 (3) |
H9B1 | 0.3659 | 0.1193 | 0.0638 | 0.046* | 0.154 (3) |
H9B2 | 0.2300 | 0.0488 | 0.0360 | 0.046* | 0.154 (3) |
H9B3 | 0.3446 | 0.0071 | 0.0675 | 0.046* | 0.154 (3) |
C10B | 0.2609 (11) | 0.0254 (8) | 0.1770 (7) | 0.0330 (5) | 0.154 (3) |
H10D | 0.1931 | −0.0261 | 0.1340 | 0.049* | 0.154 (3) |
H10E | 0.2342 | 0.0500 | 0.2252 | 0.049* | 0.154 (3) |
H10F | 0.3305 | −0.0064 | 0.1857 | 0.049* | 0.154 (3) |
B1 | 0.77548 (13) | 0.27582 (11) | 0.04141 (8) | 0.0138 (3) | |
C11 | 0.88932 (11) | 0.27236 (9) | −0.00039 (7) | 0.0136 (2) | |
C12 | 0.95590 (11) | 0.19452 (10) | −0.01608 (7) | 0.0155 (2) | |
H12 | 0.9370 | 0.1389 | −0.0002 | 0.019* | |
C13 | 1.04867 (12) | 0.19517 (11) | −0.05401 (8) | 0.0189 (3) | |
H13 | 1.0916 | 0.1410 | −0.0629 | 0.023* | |
C14 | 1.07830 (12) | 0.27478 (11) | −0.07873 (8) | 0.0193 (3) | |
H14 | 1.1417 | 0.2759 | −0.1043 | 0.023* | |
C15 | 1.01347 (12) | 0.35294 (10) | −0.06543 (8) | 0.0190 (3) | |
H15 | 1.0316 | 0.4074 | −0.0827 | 0.023* | |
C16 | 0.92198 (12) | 0.35140 (10) | −0.02680 (8) | 0.0171 (3) | |
H16 | 0.8797 | 0.4060 | −0.0179 | 0.021* | |
C17 | 0.64551 (12) | 0.25013 (10) | −0.02617 (8) | 0.0156 (2) | |
C18 | 0.53451 (12) | 0.26090 (10) | −0.00582 (8) | 0.0181 (3) | |
H18 | 0.5359 | 0.2833 | 0.0482 | 0.022* | |
C19 | 0.42312 (12) | 0.24021 (11) | −0.06130 (9) | 0.0224 (3) | |
H19 | 0.3509 | 0.2492 | −0.0447 | 0.027* | |
C20 | 0.41749 (13) | 0.20643 (11) | −0.14102 (9) | 0.0248 (3) | |
H20 | 0.3418 | 0.1921 | −0.1792 | 0.030* | |
C21 | 0.52392 (14) | 0.19396 (11) | −0.16378 (8) | 0.0248 (3) | |
H21 | 0.5211 | 0.1700 | −0.2181 | 0.030* | |
C22 | 0.63568 (13) | 0.21642 (10) | −0.10724 (8) | 0.0200 (3) | |
H2 | 0.7076 | 0.2086 | −0.1244 | 0.024* | |
C23 | 0.80202 (11) | 0.39532 (10) | 0.10867 (7) | 0.0144 (2) | |
C24 | 0.90731 (12) | 0.43503 (10) | 0.17312 (8) | 0.0195 (3) | |
H24 | 0.9599 | 0.3903 | 0.1791 | 0.023* | |
C25 | 0.93838 (13) | 0.53692 (11) | 0.22868 (8) | 0.0223 (3) | |
H25 | 1.0107 | 0.5599 | 0.2712 | 0.027* | |
C26 | 0.86385 (13) | 0.60503 (11) | 0.22215 (8) | 0.0215 (3) | |
H26 | 0.8841 | 0.6745 | 0.2599 | 0.026* | |
C27 | 0.75911 (13) | 0.56894 (10) | 0.15907 (8) | 0.0199 (3) | |
H27 | 0.7068 | 0.6141 | 0.1535 | 0.024* | |
C28 | 0.73019 (12) | 0.46676 (10) | 0.10378 (8) | 0.0166 (3) | |
H28 | 0.6586 | 0.4446 | 0.0609 | 0.020* | |
C29 | 0.77013 (11) | 0.18967 (10) | 0.08248 (7) | 0.0146 (2) | |
C30 | 0.87714 (12) | 0.17699 (10) | 0.12790 (8) | 0.0170 (3) | |
H30 | 0.9530 | 0.2229 | 0.1379 | 0.020* | |
C31 | 0.87737 (12) | 0.10107 (10) | 0.15866 (8) | 0.0182 (3) | |
H31 | 0.9523 | 0.0957 | 0.1882 | 0.022* | |
C32 | 0.76808 (13) | 0.03260 (10) | 0.14644 (8) | 0.0185 (3) | |
H32 | 0.7676 | −0.0199 | 0.1669 | 0.022* | |
C33 | 0.66014 (12) | 0.04320 (10) | 0.10369 (8) | 0.0186 (3) | |
H33 | 0.5845 | −0.0018 | 0.0954 | 0.022* | |
C34 | 0.66199 (12) | 0.11944 (10) | 0.07278 (8) | 0.0164 (2) | |
H34 | 0.5865 | 0.1244 | 0.0437 | 0.020* | |
B2 | 0.21218 (12) | 0.21890 (11) | 0.46170 (8) | 0.0132 (3) | |
C35 | 0.18977 (11) | 0.10369 (10) | 0.39032 (7) | 0.0146 (2) | |
C36 | 0.07262 (12) | 0.05578 (10) | 0.33620 (8) | 0.0162 (2) | |
H36 | 0.0083 | 0.0913 | 0.3421 | 0.019* | |
C37 | 0.04716 (13) | −0.04096 (11) | 0.27466 (8) | 0.0209 (3) | |
H37 | −0.0329 | −0.0695 | 0.2394 | 0.025* | |
C38 | 0.13855 (14) | −0.09602 (11) | 0.26452 (9) | 0.0263 (3) | |
H38 | 0.1218 | −0.1622 | 0.2228 | 0.032* | |
C39 | 0.25467 (14) | −0.05202 (11) | 0.31674 (9) | 0.0255 (3) | |
H39 | 0.3181 | −0.0886 | 0.3110 | 0.031* | |
C40 | 0.27898 (12) | 0.04579 (10) | 0.37778 (8) | 0.0190 (3) | |
H40 | 0.3596 | 0.0742 | 0.4123 | 0.023* | |
C41 | 0.09474 (11) | 0.21976 (9) | 0.49961 (7) | 0.0134 (2) | |
C42 | 0.02629 (11) | 0.29574 (10) | 0.50940 (8) | 0.0158 (2) | |
H42 | 0.0450 | 0.3485 | 0.4906 | 0.019* | |
C43 | −0.06912 (12) | 0.29718 (11) | 0.54603 (8) | 0.0213 (3) | |
H43 | −0.1141 | 0.3498 | 0.5510 | 0.026* | |
C44 | −0.09777 (12) | 0.22214 (11) | 0.57497 (8) | 0.0207 (3) | |
H44 | −0.1612 | 0.2236 | 0.6007 | 0.025* | |
C45 | −0.03243 (12) | 0.14465 (11) | 0.56592 (8) | 0.0198 (3) | |
H45 | −0.0512 | 0.0926 | 0.5854 | 0.024* | |
C46 | 0.06078 (12) | 0.14359 (10) | 0.52818 (8) | 0.0176 (3) | |
H46 | 0.1031 | 0.0891 | 0.5215 | 0.021* | |
C47 | 0.33983 (11) | 0.24479 (9) | 0.53140 (7) | 0.0143 (2) | |
C48 | 0.34464 (12) | 0.26164 (10) | 0.61014 (8) | 0.0172 (3) | |
H48 | 0.2704 | 0.2597 | 0.6253 | 0.021* | |
C49 | 0.45487 (13) | 0.28120 (11) | 0.66708 (8) | 0.0227 (3) | |
H49 | 0.4539 | 0.2924 | 0.7197 | 0.027* | |
C50 | 0.56528 (13) | 0.28439 (11) | 0.64765 (9) | 0.0243 (3) | |
H50 | 0.6397 | 0.2955 | 0.6859 | 0.029* | |
C51 | 0.56484 (12) | 0.27095 (10) | 0.57047 (9) | 0.0219 (3) | |
H51 | 0.6396 | 0.2738 | 0.5560 | 0.026* | |
C52 | 0.45479 (12) | 0.25341 (10) | 0.51484 (8) | 0.0172 (3) | |
H52 | 0.4571 | 0.2469 | 0.4633 | 0.021* | |
C53 | 0.21969 (11) | 0.31079 (10) | 0.42702 (7) | 0.0134 (2) | |
C54 | 0.15048 (11) | 0.29751 (10) | 0.35213 (7) | 0.0160 (2) | |
H54 | 0.1023 | 0.2304 | 0.3175 | 0.019* | |
C55 | 0.14934 (12) | 0.37874 (11) | 0.32625 (8) | 0.0183 (3) | |
H55 | 0.1013 | 0.3659 | 0.2749 | 0.022* | |
C56 | 0.21772 (12) | 0.47772 (10) | 0.37494 (8) | 0.0179 (3) | |
H56 | 0.2169 | 0.5330 | 0.3575 | 0.021* | |
C57 | 0.28783 (12) | 0.49490 (10) | 0.44999 (8) | 0.0183 (3) | |
H57 | 0.3352 | 0.5624 | 0.4844 | 0.022* | |
C58 | 0.28817 (12) | 0.41266 (10) | 0.47442 (8) | 0.0169 (3) | |
H58 | 0.3371 | 0.4260 | 0.5256 | 0.020* | |
O1 | 0.34685 (13) | 0.37036 (10) | 0.13799 (8) | 0.0436 (3) | |
C59 | 0.31258 (14) | 0.44161 (12) | 0.12440 (9) | 0.0257 (3) | |
C60 | 0.37217 (16) | 0.49196 (14) | 0.07953 (11) | 0.0353 (4) | |
H60A | 0.4042 | 0.5662 | 0.1119 | 0.053* | |
H60B | 0.3118 | 0.4827 | 0.0311 | 0.053* | |
H60C | 0.4398 | 0.4601 | 0.0661 | 0.053* | |
C61 | 0.20691 (17) | 0.47985 (18) | 0.15014 (11) | 0.0436 (5) | |
H61A | 0.1306 | 0.4408 | 0.1088 | 0.065* | |
H61B | 0.2178 | 0.5537 | 0.1599 | 0.065* | |
H61C | 0.2028 | 0.4702 | 0.1986 | 0.065* | |
O2 | 0.59749 (11) | 0.08463 (11) | 0.35934 (9) | 0.0449 (3) | |
C62 | 0.62729 (14) | 0.00823 (11) | 0.45296 (9) | 0.0259 (3) | |
H62A | 0.5788 | 0.0548 | 0.4785 | 0.039* | |
H62B | 0.7044 | 0.0173 | 0.4914 | 0.039* | |
H62C | 0.5808 | −0.0638 | 0.4326 | 0.039* | |
C63 | 0.65441 (13) | 0.03302 (11) | 0.38676 (9) | 0.0242 (3) | |
C64 | 0.75574 (14) | −0.00695 (13) | 0.35534 (9) | 0.0286 (3) | |
H64A | 0.7550 | 0.0038 | 0.3067 | 0.043* | |
H64B | 0.7439 | −0.0812 | 0.3443 | 0.043* | |
H64C | 0.8347 | 0.0304 | 0.3945 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0143 (5) | 0.0173 (5) | 0.0180 (5) | 0.0052 (4) | 0.0070 (4) | 0.0075 (4) |
N2 | 0.0124 (5) | 0.0165 (5) | 0.0177 (5) | 0.0045 (4) | 0.0041 (4) | 0.0046 (4) |
N3 | 0.0131 (5) | 0.0191 (5) | 0.0167 (5) | 0.0029 (4) | 0.0019 (4) | 0.0094 (4) |
C1 | 0.0139 (6) | 0.0168 (6) | 0.0105 (5) | 0.0029 (5) | 0.0032 (4) | 0.0040 (5) |
C2 | 0.0159 (6) | 0.0206 (6) | 0.0199 (6) | 0.0081 (5) | 0.0077 (5) | 0.0070 (5) |
C3 | 0.0214 (7) | 0.0247 (7) | 0.0251 (7) | 0.0066 (5) | 0.0110 (6) | 0.0157 (6) |
C4 | 0.0137 (6) | 0.0227 (7) | 0.0233 (7) | 0.0003 (5) | 0.0027 (5) | 0.0069 (6) |
C5 | 0.0174 (6) | 0.0205 (7) | 0.0302 (8) | 0.0093 (5) | 0.0066 (6) | 0.0064 (6) |
C6 | 0.0137 (6) | 0.0203 (6) | 0.0167 (6) | 0.0010 (5) | 0.0037 (5) | 0.0082 (5) |
C7 | 0.0149 (6) | 0.0249 (7) | 0.0165 (6) | 0.0003 (5) | 0.0031 (5) | 0.0031 (5) |
N4A | 0.0136 (11) | 0.0206 (6) | 0.0163 (9) | 0.0037 (5) | 0.0039 (5) | 0.0041 (6) |
C8A | 0.0192 (8) | 0.0409 (14) | 0.0380 (11) | 0.0090 (9) | 0.0061 (8) | −0.0036 (10) |
C9A | 0.0329 (10) | 0.0352 (12) | 0.0164 (8) | −0.0008 (9) | 0.0011 (7) | 0.0088 (8) |
C10A | 0.0389 (11) | 0.0190 (8) | 0.0346 (10) | −0.0014 (7) | 0.0027 (8) | 0.0101 (8) |
N4B | 0.0136 (11) | 0.0206 (6) | 0.0163 (9) | 0.0037 (5) | 0.0039 (5) | 0.0041 (6) |
C8B | 0.0192 (8) | 0.0409 (14) | 0.0380 (11) | 0.0090 (9) | 0.0061 (8) | −0.0036 (10) |
C9B | 0.0329 (10) | 0.0352 (12) | 0.0164 (8) | −0.0008 (9) | 0.0011 (7) | 0.0088 (8) |
C10B | 0.0389 (11) | 0.0190 (8) | 0.0346 (10) | −0.0014 (7) | 0.0027 (8) | 0.0101 (8) |
B1 | 0.0127 (6) | 0.0164 (6) | 0.0145 (6) | 0.0044 (5) | 0.0039 (5) | 0.0082 (5) |
C11 | 0.0124 (5) | 0.0144 (6) | 0.0129 (6) | 0.0028 (4) | 0.0023 (5) | 0.0048 (5) |
C12 | 0.0146 (6) | 0.0158 (6) | 0.0157 (6) | 0.0039 (5) | 0.0035 (5) | 0.0061 (5) |
C13 | 0.0170 (6) | 0.0236 (7) | 0.0174 (6) | 0.0086 (5) | 0.0056 (5) | 0.0078 (5) |
C14 | 0.0158 (6) | 0.0245 (7) | 0.0164 (6) | 0.0023 (5) | 0.0060 (5) | 0.0063 (5) |
C15 | 0.0210 (6) | 0.0185 (6) | 0.0174 (6) | 0.0016 (5) | 0.0069 (5) | 0.0070 (5) |
C16 | 0.0199 (6) | 0.0160 (6) | 0.0170 (6) | 0.0049 (5) | 0.0065 (5) | 0.0071 (5) |
C17 | 0.0151 (6) | 0.0135 (6) | 0.0177 (6) | 0.0041 (5) | 0.0027 (5) | 0.0061 (5) |
C18 | 0.0155 (6) | 0.0179 (6) | 0.0213 (6) | 0.0045 (5) | 0.0036 (5) | 0.0087 (5) |
C19 | 0.0151 (6) | 0.0189 (6) | 0.0322 (8) | 0.0038 (5) | 0.0026 (6) | 0.0112 (6) |
C20 | 0.0210 (7) | 0.0201 (7) | 0.0278 (7) | 0.0030 (5) | −0.0055 (6) | 0.0104 (6) |
C21 | 0.0277 (7) | 0.0239 (7) | 0.0179 (7) | 0.0044 (6) | −0.0009 (6) | 0.0070 (6) |
C22 | 0.0202 (6) | 0.0194 (6) | 0.0183 (6) | 0.0054 (5) | 0.0020 (5) | 0.0066 (5) |
C23 | 0.0142 (6) | 0.0173 (6) | 0.0143 (6) | 0.0048 (5) | 0.0063 (5) | 0.0075 (5) |
C24 | 0.0202 (6) | 0.0192 (6) | 0.0175 (6) | 0.0054 (5) | 0.0028 (5) | 0.0064 (5) |
C25 | 0.0242 (7) | 0.0213 (7) | 0.0167 (6) | 0.0025 (5) | 0.0026 (5) | 0.0047 (5) |
C26 | 0.0275 (7) | 0.0158 (6) | 0.0207 (7) | 0.0033 (5) | 0.0115 (6) | 0.0046 (5) |
C27 | 0.0229 (7) | 0.0175 (6) | 0.0254 (7) | 0.0072 (5) | 0.0121 (6) | 0.0114 (5) |
C28 | 0.0167 (6) | 0.0181 (6) | 0.0183 (6) | 0.0047 (5) | 0.0070 (5) | 0.0094 (5) |
C29 | 0.0139 (6) | 0.0163 (6) | 0.0137 (6) | 0.0038 (5) | 0.0053 (5) | 0.0051 (5) |
C30 | 0.0160 (6) | 0.0193 (6) | 0.0178 (6) | 0.0044 (5) | 0.0055 (5) | 0.0091 (5) |
C31 | 0.0189 (6) | 0.0212 (6) | 0.0159 (6) | 0.0058 (5) | 0.0039 (5) | 0.0089 (5) |
C32 | 0.0253 (7) | 0.0158 (6) | 0.0169 (6) | 0.0057 (5) | 0.0083 (5) | 0.0077 (5) |
C33 | 0.0192 (6) | 0.0166 (6) | 0.0196 (6) | 0.0016 (5) | 0.0088 (5) | 0.0055 (5) |
C34 | 0.0140 (6) | 0.0165 (6) | 0.0191 (6) | 0.0044 (5) | 0.0060 (5) | 0.0064 (5) |
B2 | 0.0125 (6) | 0.0136 (6) | 0.0139 (6) | 0.0039 (5) | 0.0033 (5) | 0.0057 (5) |
C35 | 0.0153 (6) | 0.0154 (6) | 0.0146 (6) | 0.0046 (5) | 0.0049 (5) | 0.0070 (5) |
C36 | 0.0157 (6) | 0.0167 (6) | 0.0168 (6) | 0.0044 (5) | 0.0047 (5) | 0.0070 (5) |
C37 | 0.0192 (6) | 0.0207 (7) | 0.0173 (6) | 0.0007 (5) | 0.0010 (5) | 0.0046 (5) |
C38 | 0.0288 (8) | 0.0203 (7) | 0.0215 (7) | 0.0062 (6) | 0.0043 (6) | −0.0004 (6) |
C39 | 0.0249 (7) | 0.0210 (7) | 0.0259 (7) | 0.0111 (6) | 0.0071 (6) | 0.0015 (6) |
C40 | 0.0169 (6) | 0.0183 (6) | 0.0189 (6) | 0.0055 (5) | 0.0037 (5) | 0.0041 (5) |
C41 | 0.0129 (6) | 0.0137 (6) | 0.0115 (6) | 0.0035 (4) | 0.0011 (4) | 0.0035 (5) |
C42 | 0.0147 (6) | 0.0157 (6) | 0.0171 (6) | 0.0052 (5) | 0.0038 (5) | 0.0063 (5) |
C43 | 0.0176 (6) | 0.0226 (7) | 0.0244 (7) | 0.0086 (5) | 0.0081 (5) | 0.0073 (6) |
C44 | 0.0171 (6) | 0.0242 (7) | 0.0203 (7) | 0.0043 (5) | 0.0090 (5) | 0.0060 (5) |
C45 | 0.0204 (6) | 0.0201 (6) | 0.0203 (6) | 0.0019 (5) | 0.0077 (5) | 0.0092 (5) |
C46 | 0.0189 (6) | 0.0170 (6) | 0.0196 (6) | 0.0066 (5) | 0.0072 (5) | 0.0083 (5) |
C47 | 0.0149 (6) | 0.0120 (5) | 0.0159 (6) | 0.0038 (4) | 0.0029 (5) | 0.0057 (5) |
C48 | 0.0209 (6) | 0.0142 (6) | 0.0167 (6) | 0.0045 (5) | 0.0032 (5) | 0.0072 (5) |
C49 | 0.0286 (7) | 0.0190 (6) | 0.0173 (6) | 0.0032 (5) | −0.0018 (6) | 0.0087 (5) |
C50 | 0.0209 (7) | 0.0178 (6) | 0.0279 (7) | 0.0041 (5) | −0.0069 (6) | 0.0095 (6) |
C51 | 0.0148 (6) | 0.0160 (6) | 0.0310 (8) | 0.0032 (5) | 0.0011 (6) | 0.0078 (6) |
C52 | 0.0150 (6) | 0.0160 (6) | 0.0203 (6) | 0.0043 (5) | 0.0041 (5) | 0.0070 (5) |
C53 | 0.0115 (5) | 0.0163 (6) | 0.0151 (6) | 0.0060 (4) | 0.0058 (5) | 0.0070 (5) |
C54 | 0.0142 (6) | 0.0182 (6) | 0.0153 (6) | 0.0044 (5) | 0.0030 (5) | 0.0067 (5) |
C55 | 0.0167 (6) | 0.0241 (7) | 0.0170 (6) | 0.0071 (5) | 0.0037 (5) | 0.0109 (5) |
C56 | 0.0196 (6) | 0.0199 (6) | 0.0216 (7) | 0.0098 (5) | 0.0093 (5) | 0.0130 (5) |
C57 | 0.0225 (6) | 0.0136 (6) | 0.0191 (6) | 0.0035 (5) | 0.0064 (5) | 0.0065 (5) |
C58 | 0.0200 (6) | 0.0158 (6) | 0.0149 (6) | 0.0038 (5) | 0.0037 (5) | 0.0066 (5) |
O1 | 0.0590 (8) | 0.0319 (6) | 0.0381 (7) | 0.0117 (6) | −0.0032 (6) | 0.0205 (6) |
C59 | 0.0257 (7) | 0.0268 (7) | 0.0201 (7) | 0.0040 (6) | −0.0032 (6) | 0.0100 (6) |
C60 | 0.0362 (9) | 0.0363 (9) | 0.0447 (10) | 0.0149 (7) | 0.0185 (8) | 0.0223 (8) |
C61 | 0.0336 (9) | 0.0724 (14) | 0.0310 (9) | 0.0154 (9) | 0.0115 (7) | 0.0248 (9) |
O2 | 0.0324 (6) | 0.0494 (8) | 0.0805 (10) | 0.0195 (6) | 0.0191 (6) | 0.0518 (8) |
C62 | 0.0277 (7) | 0.0211 (7) | 0.0344 (8) | 0.0084 (6) | 0.0161 (6) | 0.0120 (6) |
C63 | 0.0194 (7) | 0.0222 (7) | 0.0351 (8) | 0.0039 (5) | 0.0060 (6) | 0.0172 (6) |
C64 | 0.0273 (8) | 0.0392 (9) | 0.0296 (8) | 0.0135 (7) | 0.0131 (6) | 0.0204 (7) |
N1—C1 | 1.3308 (16) | C25—H25 | 0.9500 |
N1—C2 | 1.4668 (16) | C26—C27 | 1.390 (2) |
N1—C3 | 1.4674 (16) | C26—H26 | 0.9500 |
N2—C1 | 1.3425 (16) | C27—C28 | 1.3967 (19) |
N2—C4 | 1.4609 (17) | C27—H27 | 0.9500 |
N2—C5 | 1.4628 (17) | C28—H28 | 0.9500 |
N3—C1 | 1.3508 (16) | C29—C34 | 1.4120 (17) |
N3—C6 | 1.4612 (16) | C29—C30 | 1.4154 (18) |
N3—H3 | 0.855 (19) | C30—C31 | 1.3888 (18) |
C2—H2A | 0.9800 | C30—H30 | 0.9500 |
C2—H2B | 0.9800 | C31—C32 | 1.3955 (19) |
C2—H2C | 0.9800 | C31—H31 | 0.9500 |
C3—H3A | 0.9800 | C32—C33 | 1.3875 (19) |
C3—H3B | 0.9800 | C32—H32 | 0.9500 |
C3—H3C | 0.9800 | C33—C34 | 1.3945 (18) |
C4—H4A | 0.9800 | C33—H33 | 0.9500 |
C4—H4B | 0.9800 | C34—H34 | 0.9500 |
C4—H4C | 0.9800 | B2—C41 | 1.6457 (18) |
C5—H5A | 0.9800 | B2—C53 | 1.6478 (18) |
C5—H5B | 0.9800 | B2—C47 | 1.6496 (18) |
C5—H5C | 0.9800 | B2—C35 | 1.6524 (18) |
C6—C7 | 1.5286 (18) | C35—C40 | 1.4001 (18) |
C6—H6A | 0.9900 | C35—C36 | 1.4141 (18) |
C6—H6B | 0.9900 | C36—C37 | 1.3917 (19) |
C7—N4A | 1.504 (5) | C36—H36 | 0.9500 |
C7—N4B | 1.55 (3) | C37—C38 | 1.392 (2) |
C7—H7A | 0.9900 | C37—H37 | 0.9500 |
C7—H7B | 0.9900 | C38—C39 | 1.388 (2) |
N4A—C8A | 1.487 (3) | C38—H38 | 0.9500 |
N4A—C10A | 1.501 (3) | C39—C40 | 1.3989 (19) |
N4A—C9A | 1.504 (3) | C39—H39 | 0.9500 |
C8A—H8A1 | 0.9800 | C40—H40 | 0.9500 |
C8A—H8A2 | 0.9800 | C41—C42 | 1.3975 (17) |
C8A—H8A3 | 0.9800 | C41—C46 | 1.4078 (17) |
C9A—H9A1 | 0.9800 | C42—C43 | 1.4051 (18) |
C9A—H9A2 | 0.9800 | C42—H42 | 0.9500 |
C9A—H9A3 | 0.9800 | C43—C44 | 1.385 (2) |
C10A—H10A | 0.9800 | C43—H43 | 0.9500 |
C10A—H10B | 0.9800 | C44—C45 | 1.391 (2) |
C10A—H10C | 0.9800 | C44—H44 | 0.9500 |
N4B—C8B | 1.464 (17) | C45—C46 | 1.3970 (18) |
N4B—C9B | 1.491 (17) | C45—H45 | 0.9500 |
N4B—C10B | 1.508 (17) | C46—H46 | 0.9500 |
C8B—H8B1 | 0.9800 | C47—C48 | 1.4060 (18) |
C8B—H8B2 | 0.9800 | C47—C52 | 1.4119 (18) |
C8B—H8B3 | 0.9800 | C48—C49 | 1.3997 (19) |
C9B—H9B1 | 0.9800 | C48—H48 | 0.9500 |
C9B—H9B2 | 0.9800 | C49—C50 | 1.385 (2) |
C9B—H9B3 | 0.9800 | C49—H49 | 0.9500 |
C10B—H10D | 0.9800 | C50—C51 | 1.398 (2) |
C10B—H10E | 0.9800 | C50—H50 | 0.9500 |
C10B—H10F | 0.9800 | C51—C52 | 1.3916 (18) |
B1—C17 | 1.6478 (18) | C51—H51 | 0.9500 |
B1—C11 | 1.6525 (18) | C52—H52 | 0.9500 |
B1—C23 | 1.6578 (19) | C53—C54 | 1.4034 (17) |
B1—C29 | 1.6588 (18) | C53—C58 | 1.4088 (18) |
C11—C12 | 1.4048 (17) | C54—C55 | 1.3983 (18) |
C11—C16 | 1.4113 (17) | C54—H54 | 0.9500 |
C12—C13 | 1.3967 (18) | C55—C56 | 1.3835 (19) |
C12—H12 | 0.9500 | C55—H55 | 0.9500 |
C13—C14 | 1.3893 (19) | C56—C57 | 1.3940 (19) |
C13—H13 | 0.9500 | C56—H56 | 0.9500 |
C14—C15 | 1.393 (2) | C57—C58 | 1.3940 (18) |
C14—H14 | 0.9500 | C57—H57 | 0.9500 |
C15—C16 | 1.3941 (18) | C58—H58 | 0.9500 |
C15—H15 | 0.9500 | O1—C59 | 1.2185 (19) |
C16—H16 | 0.9500 | C59—C60 | 1.488 (2) |
C17—C22 | 1.4059 (19) | C59—C61 | 1.492 (2) |
C17—C18 | 1.4124 (18) | C60—H60A | 0.9800 |
C18—C19 | 1.3927 (19) | C60—H60B | 0.9800 |
C18—H18 | 0.9500 | C60—H60C | 0.9800 |
C19—C20 | 1.392 (2) | C61—H61A | 0.9800 |
C19—H19 | 0.9500 | C61—H61B | 0.9800 |
C20—C21 | 1.385 (2) | C61—H61C | 0.9800 |
C20—H20 | 0.9500 | O2—C63 | 1.2177 (18) |
C21—C22 | 1.4012 (19) | C62—C63 | 1.488 (2) |
C21—H21 | 0.9500 | C62—H62A | 0.9800 |
C22—H2 | 0.9500 | C62—H62B | 0.9800 |
C23—C28 | 1.4027 (18) | C62—H62C | 0.9800 |
C23—C24 | 1.4058 (18) | C63—C64 | 1.497 (2) |
C24—C25 | 1.3941 (19) | C64—H64A | 0.9800 |
C24—H24 | 0.9500 | C64—H64B | 0.9800 |
C25—C26 | 1.392 (2) | C64—H64C | 0.9800 |
C1—N1—C2 | 122.30 (11) | C25—C24—C23 | 123.20 (13) |
C1—N1—C3 | 122.05 (11) | C25—C24—H24 | 118.4 |
C2—N1—C3 | 115.58 (10) | C23—C24—H24 | 118.4 |
C1—N2—C4 | 122.22 (11) | C26—C25—C24 | 120.24 (13) |
C1—N2—C5 | 121.68 (11) | C26—C25—H25 | 119.9 |
C4—N2—C5 | 115.46 (11) | C24—C25—H25 | 119.9 |
C1—N3—C6 | 125.43 (11) | C27—C26—C25 | 118.37 (12) |
C1—N3—H3 | 118.1 (12) | C27—C26—H26 | 120.8 |
C6—N3—H3 | 115.5 (12) | C25—C26—H26 | 120.8 |
N1—C1—N2 | 120.62 (11) | C26—C27—C28 | 120.43 (13) |
N1—C1—N3 | 121.02 (11) | C26—C27—H27 | 119.8 |
N2—C1—N3 | 118.36 (12) | C28—C27—H27 | 119.8 |
N1—C2—H2A | 109.5 | C27—C28—C23 | 123.01 (12) |
N1—C2—H2B | 109.5 | C27—C28—H28 | 118.5 |
H2A—C2—H2B | 109.5 | C23—C28—H28 | 118.5 |
N1—C2—H2C | 109.5 | C34—C29—C30 | 113.77 (11) |
H2A—C2—H2C | 109.5 | C34—C29—B1 | 124.20 (11) |
H2B—C2—H2C | 109.5 | C30—C29—B1 | 121.96 (11) |
N1—C3—H3A | 109.5 | C31—C30—C29 | 123.60 (12) |
N1—C3—H3B | 109.5 | C31—C30—H30 | 118.2 |
H3A—C3—H3B | 109.5 | C29—C30—H30 | 118.2 |
N1—C3—H3C | 109.5 | C30—C31—C32 | 120.34 (12) |
H3A—C3—H3C | 109.5 | C30—C31—H31 | 119.8 |
H3B—C3—H3C | 109.5 | C32—C31—H31 | 119.8 |
N2—C4—H4A | 109.5 | C33—C32—C31 | 118.33 (12) |
N2—C4—H4B | 109.5 | C33—C32—H32 | 120.8 |
H4A—C4—H4B | 109.5 | C31—C32—H32 | 120.8 |
N2—C4—H4C | 109.5 | C32—C33—C34 | 120.45 (12) |
H4A—C4—H4C | 109.5 | C32—C33—H33 | 119.8 |
H4B—C4—H4C | 109.5 | C34—C33—H33 | 119.8 |
N2—C5—H5A | 109.5 | C33—C34—C29 | 123.50 (12) |
N2—C5—H5B | 109.5 | C33—C34—H34 | 118.2 |
H5A—C5—H5B | 109.5 | C29—C34—H34 | 118.2 |
N2—C5—H5C | 109.5 | C41—B2—C53 | 108.14 (10) |
H5A—C5—H5C | 109.5 | C41—B2—C47 | 109.45 (10) |
H5B—C5—H5C | 109.5 | C53—B2—C47 | 108.60 (10) |
N3—C6—C7 | 110.06 (10) | C41—B2—C35 | 108.30 (10) |
N3—C6—H6A | 109.6 | C53—B2—C35 | 110.78 (10) |
C7—C6—H6A | 109.6 | C47—B2—C35 | 111.51 (10) |
N3—C6—H6B | 109.6 | C40—C35—C36 | 114.79 (11) |
C7—C6—H6B | 109.6 | C40—C35—B2 | 125.26 (11) |
H6A—C6—H6B | 108.2 | C36—C35—B2 | 119.95 (11) |
N4A—C7—C6 | 114.75 (14) | C37—C36—C35 | 123.07 (12) |
C6—C7—N4B | 108.6 (6) | C37—C36—H36 | 118.5 |
N4A—C7—H7A | 108.6 | C35—C36—H36 | 118.5 |
C6—C7—H7A | 108.6 | C36—C37—C38 | 120.22 (12) |
N4A—C7—H7B | 108.6 | C36—C37—H37 | 119.9 |
C6—C7—H7B | 108.6 | C38—C37—H37 | 119.9 |
H7A—C7—H7B | 107.6 | C39—C38—C37 | 118.52 (13) |
C8A—N4A—C10A | 110.4 (3) | C39—C38—H38 | 120.7 |
C8A—N4A—C7 | 112.2 (2) | C37—C38—H38 | 120.7 |
C10A—N4A—C7 | 108.6 (3) | C38—C39—C40 | 120.50 (13) |
C8A—N4A—C9A | 110.0 (3) | C38—C39—H39 | 119.7 |
C10A—N4A—C9A | 107.2 (2) | C40—C39—H39 | 119.7 |
C7—N4A—C9A | 108.3 (2) | C39—C40—C35 | 122.89 (12) |
N4A—C8A—H8A1 | 109.5 | C39—C40—H40 | 118.6 |
N4A—C8A—H8A2 | 109.5 | C35—C40—H40 | 118.6 |
H8A1—C8A—H8A2 | 109.5 | C42—C41—C46 | 115.46 (11) |
N4A—C8A—H8A3 | 109.5 | C42—C41—B2 | 124.15 (11) |
H8A1—C8A—H8A3 | 109.5 | C46—C41—B2 | 120.33 (11) |
H8A2—C8A—H8A3 | 109.5 | C41—C42—C43 | 122.56 (12) |
N4A—C9A—H9A1 | 109.5 | C41—C42—H42 | 118.7 |
N4A—C9A—H9A2 | 109.5 | C43—C42—H42 | 118.7 |
H9A1—C9A—H9A2 | 109.5 | C44—C43—C42 | 120.17 (12) |
N4A—C9A—H9A3 | 109.5 | C44—C43—H43 | 119.9 |
H9A1—C9A—H9A3 | 109.5 | C42—C43—H43 | 119.9 |
H9A2—C9A—H9A3 | 109.5 | C43—C44—C45 | 119.10 (12) |
N4A—C10A—H10A | 109.5 | C43—C44—H44 | 120.5 |
N4A—C10A—H10B | 109.5 | C45—C44—H44 | 120.5 |
H10A—C10A—H10B | 109.5 | C44—C45—C46 | 119.87 (12) |
N4A—C10A—H10C | 109.5 | C44—C45—H45 | 120.1 |
H10A—C10A—H10C | 109.5 | C46—C45—H45 | 120.1 |
H10B—C10A—H10C | 109.5 | C45—C46—C41 | 122.82 (12) |
C8B—N4B—C9B | 111.1 (16) | C45—C46—H46 | 118.6 |
C8B—N4B—C10B | 111.3 (16) | C41—C46—H46 | 118.6 |
C9B—N4B—C10B | 105.4 (14) | C48—C47—C52 | 115.03 (11) |
C8B—N4B—C7 | 106.7 (14) | C48—C47—B2 | 124.28 (11) |
C9B—N4B—C7 | 105.0 (13) | C52—C47—B2 | 120.68 (11) |
C10B—N4B—C7 | 117.2 (15) | C49—C48—C47 | 122.40 (13) |
N4B—C8B—H8B1 | 109.5 | C49—C48—H48 | 118.8 |
N4B—C8B—H8B2 | 109.5 | C47—C48—H48 | 118.8 |
H8B1—C8B—H8B2 | 109.5 | C50—C49—C48 | 120.80 (13) |
N4B—C8B—H8B3 | 109.5 | C50—C49—H49 | 119.6 |
H8B1—C8B—H8B3 | 109.5 | C48—C49—H49 | 119.6 |
H8B2—C8B—H8B3 | 109.5 | C49—C50—C51 | 118.56 (12) |
N4B—C9B—H9B1 | 109.5 | C49—C50—H50 | 120.7 |
N4B—C9B—H9B2 | 109.5 | C51—C50—H50 | 120.7 |
H9B1—C9B—H9B2 | 109.5 | C52—C51—C50 | 119.99 (13) |
N4B—C9B—H9B3 | 109.5 | C52—C51—H51 | 120.0 |
H9B1—C9B—H9B3 | 109.5 | C50—C51—H51 | 120.0 |
H9B2—C9B—H9B3 | 109.5 | C51—C52—C47 | 123.11 (13) |
N4B—C10B—H10D | 109.5 | C51—C52—H52 | 118.4 |
N4B—C10B—H10E | 109.5 | C47—C52—H52 | 118.4 |
H10D—C10B—H10E | 109.5 | C54—C53—C58 | 114.75 (11) |
N4B—C10B—H10F | 109.5 | C54—C53—B2 | 123.50 (11) |
H10D—C10B—H10F | 109.5 | C58—C53—B2 | 121.47 (11) |
H10E—C10B—H10F | 109.5 | C55—C54—C53 | 122.84 (12) |
C17—B1—C11 | 108.93 (10) | C55—C54—H54 | 118.6 |
C17—B1—C23 | 109.99 (10) | C53—C54—H54 | 118.6 |
C11—B1—C23 | 106.64 (10) | C56—C55—C54 | 120.43 (12) |
C17—B1—C29 | 109.94 (10) | C56—C55—H55 | 119.8 |
C11—B1—C29 | 110.37 (10) | C54—C55—H55 | 119.8 |
C23—B1—C29 | 110.91 (10) | C55—C56—C57 | 118.89 (12) |
C12—C11—C16 | 114.93 (11) | C55—C56—H56 | 120.6 |
C12—C11—B1 | 126.24 (11) | C57—C56—H56 | 120.6 |
C16—C11—B1 | 118.76 (11) | C56—C57—C58 | 119.72 (12) |
C13—C12—C11 | 123.01 (12) | C56—C57—H57 | 120.1 |
C13—C12—H12 | 118.5 | C58—C57—H57 | 120.1 |
C11—C12—H12 | 118.5 | C57—C58—C53 | 123.36 (12) |
C14—C13—C12 | 120.17 (12) | C57—C58—H58 | 118.3 |
C14—C13—H13 | 119.9 | C53—C58—H58 | 118.3 |
C12—C13—H13 | 119.9 | O1—C59—C60 | 121.36 (16) |
C13—C14—C15 | 118.84 (12) | O1—C59—C61 | 121.27 (16) |
C13—C14—H14 | 120.6 | C60—C59—C61 | 117.35 (14) |
C15—C14—H14 | 120.6 | C59—C60—H60A | 109.5 |
C14—C15—C16 | 120.11 (12) | C59—C60—H60B | 109.5 |
C14—C15—H15 | 119.9 | H60A—C60—H60B | 109.5 |
C16—C15—H15 | 119.9 | C59—C60—H60C | 109.5 |
C15—C16—C11 | 122.93 (12) | H60A—C60—H60C | 109.5 |
C15—C16—H16 | 118.5 | H60B—C60—H60C | 109.5 |
C11—C16—H16 | 118.5 | C59—C61—H61A | 109.5 |
C22—C17—C18 | 114.99 (12) | C59—C61—H61B | 109.5 |
C22—C17—B1 | 123.53 (11) | H61A—C61—H61B | 109.5 |
C18—C17—B1 | 121.48 (11) | C59—C61—H61C | 109.5 |
C19—C18—C17 | 123.04 (13) | H61A—C61—H61C | 109.5 |
C19—C18—H18 | 118.5 | H61B—C61—H61C | 109.5 |
C17—C18—H18 | 118.5 | C63—C62—H62A | 109.5 |
C20—C19—C18 | 120.03 (13) | C63—C62—H62B | 109.5 |
C20—C19—H19 | 120.0 | H62A—C62—H62B | 109.5 |
C18—C19—H19 | 120.0 | C63—C62—H62C | 109.5 |
C21—C20—C19 | 118.94 (13) | H62A—C62—H62C | 109.5 |
C21—C20—H20 | 120.5 | H62B—C62—H62C | 109.5 |
C19—C20—H20 | 120.5 | O2—C63—C62 | 121.64 (14) |
C20—C21—C22 | 120.42 (13) | O2—C63—C64 | 120.87 (14) |
C20—C21—H21 | 119.8 | C62—C63—C64 | 117.48 (12) |
C22—C21—H21 | 119.8 | C63—C64—H64A | 109.5 |
C21—C22—C17 | 122.56 (13) | C63—C64—H64B | 109.5 |
C21—C22—H2 | 118.7 | H64A—C64—H64B | 109.5 |
C17—C22—H2 | 118.7 | C63—C64—H64C | 109.5 |
C28—C23—C24 | 114.74 (12) | H64A—C64—H64C | 109.5 |
C28—C23—B1 | 124.38 (11) | H64B—C64—H64C | 109.5 |
C24—C23—B1 | 120.69 (11) | ||
C2—N1—C1—N2 | −151.36 (12) | C23—B1—C29—C30 | −73.78 (15) |
C3—N1—C1—N2 | 31.64 (18) | C34—C29—C30—C31 | 1.59 (19) |
C2—N1—C1—N3 | 29.01 (18) | B1—C29—C30—C31 | −175.45 (12) |
C3—N1—C1—N3 | −147.99 (12) | C29—C30—C31—C32 | −0.8 (2) |
C4—N2—C1—N1 | 34.13 (18) | C30—C31—C32—C33 | −0.6 (2) |
C5—N2—C1—N1 | −155.46 (12) | C31—C32—C33—C34 | 1.1 (2) |
C4—N2—C1—N3 | −146.24 (12) | C32—C33—C34—C29 | −0.2 (2) |
C5—N2—C1—N3 | 24.18 (18) | C30—C29—C34—C33 | −1.07 (19) |
C6—N3—C1—N1 | 35.61 (19) | B1—C29—C34—C33 | 175.89 (12) |
C6—N3—C1—N2 | −144.03 (13) | C41—B2—C35—C40 | −136.36 (12) |
C1—N3—C6—C7 | 46.52 (17) | C53—B2—C35—C40 | 105.20 (14) |
N3—C6—C7—N4A | 162.38 (16) | C47—B2—C35—C40 | −15.88 (17) |
N3—C6—C7—N4B | 166.3 (7) | C41—B2—C35—C36 | 43.17 (15) |
C6—C7—N4A—C8A | 47.0 (3) | C53—B2—C35—C36 | −75.27 (14) |
C6—C7—N4A—C10A | −75.3 (2) | C47—B2—C35—C36 | 163.65 (11) |
C6—C7—N4A—C9A | 168.60 (17) | C40—C35—C36—C37 | −0.51 (19) |
C6—C7—N4B—C8B | 80.1 (11) | B2—C35—C36—C37 | 179.91 (12) |
C6—C7—N4B—C9B | −161.9 (9) | C35—C36—C37—C38 | 0.8 (2) |
C6—C7—N4B—C10B | −45.3 (13) | C36—C37—C38—C39 | −0.3 (2) |
C17—B1—C11—C12 | −107.20 (13) | C37—C38—C39—C40 | −0.4 (2) |
C23—B1—C11—C12 | 134.13 (12) | C38—C39—C40—C35 | 0.6 (2) |
C29—B1—C11—C12 | 13.59 (17) | C36—C35—C40—C39 | −0.18 (19) |
C17—B1—C11—C16 | 69.79 (14) | B2—C35—C40—C39 | 179.37 (13) |
C23—B1—C11—C16 | −48.87 (14) | C53—B2—C41—C42 | −8.02 (16) |
C29—B1—C11—C16 | −169.42 (11) | C47—B2—C41—C42 | 110.12 (13) |
C16—C11—C12—C13 | 0.78 (18) | C35—B2—C41—C42 | −128.12 (12) |
B1—C11—C12—C13 | 177.87 (12) | C53—B2—C41—C46 | 175.05 (11) |
C11—C12—C13—C14 | −0.5 (2) | C47—B2—C41—C46 | −66.81 (14) |
C12—C13—C14—C15 | −0.41 (19) | C35—B2—C41—C46 | 54.95 (14) |
C13—C14—C15—C16 | 1.02 (19) | C46—C41—C42—C43 | 0.71 (18) |
C14—C15—C16—C11 | −0.7 (2) | B2—C41—C42—C43 | −176.35 (12) |
C12—C11—C16—C15 | −0.15 (18) | C41—C42—C43—C44 | 0.8 (2) |
B1—C11—C16—C15 | −177.47 (12) | C42—C43—C44—C45 | −1.2 (2) |
C11—B1—C17—C22 | 8.33 (16) | C43—C44—C45—C46 | 0.1 (2) |
C23—B1—C17—C22 | 124.87 (13) | C44—C45—C46—C41 | 1.4 (2) |
C29—B1—C17—C22 | −112.72 (13) | C42—C41—C46—C45 | −1.80 (19) |
C11—B1—C17—C18 | −171.63 (11) | B2—C41—C46—C45 | 175.39 (12) |
C23—B1—C17—C18 | −55.09 (15) | C41—B2—C47—C48 | 1.73 (16) |
C29—B1—C17—C18 | 67.32 (15) | C53—B2—C47—C48 | 119.59 (13) |
C22—C17—C18—C19 | −0.17 (19) | C35—B2—C47—C48 | −118.07 (13) |
B1—C17—C18—C19 | 179.80 (12) | C41—B2—C47—C52 | −177.06 (11) |
C17—C18—C19—C20 | 0.5 (2) | C53—B2—C47—C52 | −59.21 (15) |
C18—C19—C20—C21 | 0.0 (2) | C35—B2—C47—C52 | 63.13 (15) |
C19—C20—C21—C22 | −0.9 (2) | C52—C47—C48—C49 | −2.56 (18) |
C20—C21—C22—C17 | 1.3 (2) | B2—C47—C48—C49 | 178.59 (12) |
C18—C17—C22—C21 | −0.73 (19) | C47—C48—C49—C50 | −0.2 (2) |
B1—C17—C22—C21 | 179.31 (12) | C48—C49—C50—C51 | 2.0 (2) |
C17—B1—C23—C28 | −5.93 (16) | C49—C50—C51—C52 | −0.9 (2) |
C11—B1—C23—C28 | 112.04 (13) | C50—C51—C52—C47 | −2.2 (2) |
C29—B1—C23—C28 | −127.76 (12) | C48—C47—C52—C51 | 3.77 (19) |
C17—B1—C23—C24 | 179.36 (11) | B2—C47—C52—C51 | −177.33 (12) |
C11—B1—C23—C24 | −62.67 (14) | C41—B2—C53—C54 | −83.82 (14) |
C29—B1—C23—C24 | 57.53 (15) | C47—B2—C53—C54 | 157.49 (11) |
C28—C23—C24—C25 | 0.61 (19) | C35—B2—C53—C54 | 34.71 (16) |
B1—C23—C24—C25 | 175.80 (12) | C41—B2—C53—C58 | 89.73 (13) |
C23—C24—C25—C26 | 0.1 (2) | C47—B2—C53—C58 | −28.96 (16) |
C24—C25—C26—C27 | −0.3 (2) | C35—B2—C53—C58 | −151.74 (11) |
C25—C26—C27—C28 | −0.1 (2) | C58—C53—C54—C55 | 0.06 (18) |
C26—C27—C28—C23 | 0.9 (2) | B2—C53—C54—C55 | 174.00 (12) |
C24—C23—C28—C27 | −1.07 (18) | C53—C54—C55—C56 | −0.3 (2) |
B1—C23—C28—C27 | −176.05 (12) | C54—C55—C56—C57 | 0.2 (2) |
C17—B1—C29—C34 | −12.37 (17) | C55—C56—C57—C58 | 0.2 (2) |
C11—B1—C29—C34 | −132.55 (12) | C56—C57—C58—C53 | −0.5 (2) |
C23—B1—C29—C34 | 109.49 (13) | C54—C53—C58—C57 | 0.32 (19) |
C17—B1—C29—C30 | 164.36 (11) | B2—C53—C58—C57 | −173.75 (12) |
C11—B1—C29—C30 | 44.17 (16) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C23–C28, C29–C34, C35–C40 and C53–C58 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.86 (2) | 2.07 (2) | 2.777 (2) | 140 (2) |
C9A—H9A3···O1 | 0.98 | 2.48 | 3.329 (2) | 144 |
C8B—H8B1···O1 | 0.98 | 2.20 | 3.131 (2) | 158 |
C7—H7A···O1 | 0.99 | 2.43 | 3.353 (2) | 155 |
C3—H3C···Cg1 | 0.98 | 2.68 | 3.306 (2) | 122 |
C9A—H9A1···Cg2i | 0.98 | 3.11 | 3.612 (2) | 130 |
C9B—H9B2···Cg2i | 0.98 | 2.95 | 3.409 (2) | 110 |
C10B—H10E···Cg3 | 0.98 | 2.48 | 3.337 (2) | 146 |
C2—H2C···Cg4 | 0.98 | 2.98 | 3.543 (2) | 118 |
Symmetry code: (i) −x+1, −y, −z. |
Acknowledgements
The authors thank Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for measuring the diffraction data.
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