organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

N,N,N′,N′-Tetra­methyl-N′′-[2-(tri­methyl­aza­nium­yl)eth­yl]guanidinium bis­­(tetra­phenyl­borate) acetone disolvate

CROSSMARK_Color_square_no_text.svg

aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
*Correspondence e-mail: willi.kantlehner@hs-aalen.de

Edited by M. Zeller, Youngstown State University, USA (Received 19 January 2016; accepted 20 January 2016; online 6 February 2016)

The asymmetric unit of the title solvated salt, C10H26N42+·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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

ω-Amino­alkyl­guanidines like N′′-[2-(di­methyl­amino)­eth­yl]- N,N,N′,N′-tetra­methyl­guanidine (Tiritiris & Kantlehner, 2012[Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.]) and its corresponding imine-nitro­gen atom protonated guanidinium salts are well known in the literature (tetra­phenyl­borate salt: Tiritiris & Kantlehner, 2012[Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.]; bicarbonate salt: Tiritiris et al., 2011[Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.]). 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 anion exchange with sodium tetra­phenyl­borate, the here-presented crystalline title compound emerged. The asymmetric unit of the structure comprises one cation, two tetra­phenyl­borate ions and two acetone mol­ecules (Fig. 1[link]). 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[link]). 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].

[Figure 1]
Figure 1
The structure of the title compound, with displacement ellipsoids at the 50% probability level. All H atoms (except for H3) have been omitted for the sake of clarity. Only the major population of the disordered [NMe3]+ group is shown.
[Figure 2]
Figure 2
The structure of the guanidinium ion. All hydrogen atoms (except for H3) are omitted for the sake of clarity. The nitro­gen and carbon atoms of the terminal [NMe3]+ group are disordered between the opaque (minor population) and dark (major population) positions.

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[Tiritiris, I. (2013b). Acta Cryst. E69, o337-o338.]). The bond lengths and angles in both tetra­phenyl­borate ions are in good agreement with the data from the crystal structure analysis of the alkali metal tetra­phenyl­borates (Behrens et al., 2012a[Behrens, U., Hoffmann, F. & Olbrich, F. (2012a). Organometallics, 31, 905-913.]).

In the crystal, the guanidinium ion is connected by N—H⋯O and C—H⋯O hydrogen bonds (Fig. 3[link]) with the acetone mol­ecules (Table 1[link]). 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[link]). This leads to the formation of a two-dimensional supra­molecular pattern along the ac plane (Fig. 4[link]). Such C—H⋯π inter­actions have been also observed in N-[3-(benzyl­dimethyl­aza­nium­yl)prop­yl]-N′,N′,N′′,N′′-tetra­methyl­guanidinium bis­(tetra­phenyl­borate) (Tiritiris, 2013a[Tiritiris, I. (2013a). Acta Cryst. E69, o899.]) and N,N,N′,N′-tetra­methyl-N′′-[3-(tri­methyl­aza­nium­yl)prop­yl]guanidinium bis­(tetra­phenyl­borate) acetone disolvate (Tiritiris, 2013b[Tiritiris, I. (2013b). Acta Cryst. E69, o337-o338.]).

Table 1
Hydrogen-bond geometry (Å, °)

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 DA 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—H3CCg1 0.98 2.68 3.306 (2) 122
C9A—H9A1⋯Cg2i 0.98 3.11 3.612 (2) 115
C9B—H9B2⋯Cg2i 0.98 2.95 3.409 (2) 110
C10B—H10ECg3 0.98 2.48 3.337 (2) 146
C2—H2CCg4 0.98 2.98 3.543 (2) 108
Symmetry code: (i) -x+1, -y, -z.
[Figure 3]
Figure 3
N—H⋯O and C—H⋯O hydrogen bonds (black dashed lines) between the guanidinium ion and the acetone mol­ecules, including the minor population (opaque) and major population (dark) of the disordered [NMe3]+ group.
[Figure 4]
Figure 4
C—H⋯π inter­actions (brown dashed lines) between the hydrogen atoms of the guanidinium ion and the phenyl rings (centroids) of the tetra­phenyl­borate ions (view along bc), including the minor population (opaque) and major population (dark) of the disordered [NMe3]+ group.

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[Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.]) 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 refinement details are summarized in Table 2[link]. 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.

Table 2
Experimental details

Crystal data
Chemical formula C10H26N42+·2C24H20B·2C3H6O
Mr 956.92
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 11.4419 (3), 14.1461 (5), 18.8503 (9)
α, β, γ (°) 110.6352 (13), 101.824 (1), 97.8879 (8)
V3) 2720.70 (18)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.33 × 0.24 × 0.13
 
Data collection
Diffractometer Bruker–Nonius KappaCCD
No. of measured, independent and observed [I > 2σ(I)] reflections 22310, 13295, 10609
Rint 0.021
(sin θ/λ)max−1) 0.666
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.138, 1.02
No. of reflections 13295
No. of parameters 680
No. of restraints 6
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.58, −0.32
Computer programs: COLLECT (Hooft, 2004[Hooft, R. W. W. (2004). COLLECT. Bruker-Nonius BV, Delft, The Netherlands.]), DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, D-53002 Bonn, Germany.]).

Structural data


Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: 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).

N,N,N',N'-Tetramethyl-N''-[2-(trimethylazaniumyl)ethyl]guanidinium bis(tetraphenylborate) acetone disolvate top
Crystal data top
C10H26N42+·2C24H20B·2C3H6OZ = 2
Mr = 956.92F(000) = 1032
Triclinic, P1Dx = 1.168 Mg m3
a = 11.4419 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.1461 (5) ÅCell parameters from 11355 reflections
c = 18.8503 (9) Åθ = 0.4–28.3°
α = 110.6352 (13)°µ = 0.07 mm1
β = 101.824 (1)°T = 100 K
γ = 97.8879 (8)°Block, colorless
V = 2720.70 (18) Å30.33 × 0.24 × 0.13 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
10609 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 28.3°, θmin = 1.2°
φ scans, and ω scansh = 1515
22310 measured reflectionsk = 1618
13295 independent reflectionsl = 2425
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: mixed
wR(F2) = 0.138H 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 parametersΔρmax = 0.58 e Å3
6 restraintsΔρmin = 0.32 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.59093 (10)0.41666 (8)0.31479 (6)0.0158 (2)
N20.75655 (10)0.34377 (8)0.34002 (6)0.0160 (2)
N30.56432 (10)0.26444 (9)0.33777 (7)0.0160 (2)
H30.5979 (17)0.2332 (14)0.3649 (11)0.030 (5)*
C10.63681 (11)0.34267 (10)0.33081 (7)0.0142 (2)
C20.48354 (12)0.44848 (11)0.33871 (8)0.0182 (3)
H2A0.41080.41690.29330.027*
H2B0.49710.52420.35820.027*
H2C0.47100.42560.38060.027*
C30.64100 (13)0.46827 (11)0.26869 (8)0.0212 (3)
H3A0.68520.53960.30350.032*
H3B0.57380.46940.22760.032*
H3C0.69750.43030.24430.032*
C40.85097 (12)0.44027 (11)0.37520 (8)0.0213 (3)
H4A0.81330.49910.39470.032*
H4B0.89050.44790.33540.032*
H4C0.91250.43860.41910.032*
C50.80177 (13)0.24885 (11)0.32670 (9)0.0232 (3)
H5A0.82480.23980.37650.035*
H5B0.87360.25400.30630.035*
H5C0.73720.18920.28830.035*
C60.43715 (11)0.21537 (10)0.29157 (7)0.0170 (3)
H6A0.38350.26250.31010.020*
H6B0.41050.15060.29890.020*
C70.42530 (12)0.19057 (11)0.20429 (8)0.0208 (3)
H7A0.42790.25580.19550.025*
H7B0.49710.16400.19110.025*
N4A0.3105 (4)0.1127 (3)0.1488 (2)0.0178 (4)0.846 (3)
C8A0.19893 (18)0.1358 (2)0.17388 (14)0.0382 (6)0.846 (3)
H8A10.20640.13480.22630.057*0.846 (3)
H8A20.12650.08330.13620.057*0.846 (3)
H8A30.19030.20450.17560.057*0.846 (3)
C9A0.29953 (19)0.11284 (18)0.06795 (11)0.0304 (5)0.846 (3)
H9A10.23250.05540.02950.046*0.846 (3)
H9A20.37660.10450.05410.046*0.846 (3)
H9A30.28240.17870.06760.046*0.846 (3)
C10A0.32390 (19)0.00665 (14)0.14393 (12)0.0330 (5)0.846 (3)
H10A0.32620.00240.19490.049*0.846 (3)
H10B0.40020.00590.13040.049*0.846 (3)
H10C0.25410.04570.10330.049*0.846 (3)
N4B0.299 (2)0.1157 (16)0.1554 (13)0.0178 (4)0.154 (3)
C8B0.2084 (11)0.1796 (11)0.1593 (8)0.0382 (6)0.154 (3)
H8B10.23250.23450.14120.057*0.154 (3)
H8B20.20400.21090.21380.057*0.154 (3)
H8B30.12790.13610.12550.057*0.154 (3)
C9B0.3109 (11)0.0687 (10)0.0737 (6)0.0304 (5)0.154 (3)
H9B10.36590.11930.06380.046*0.154 (3)
H9B20.23000.04880.03600.046*0.154 (3)
H9B30.34460.00710.06750.046*0.154 (3)
C10B0.2609 (11)0.0254 (8)0.1770 (7)0.0330 (5)0.154 (3)
H10D0.19310.02610.13400.049*0.154 (3)
H10E0.23420.05000.22520.049*0.154 (3)
H10F0.33050.00640.18570.049*0.154 (3)
B10.77548 (13)0.27582 (11)0.04141 (8)0.0138 (3)
C110.88932 (11)0.27236 (9)0.00039 (7)0.0136 (2)
C120.95590 (11)0.19452 (10)0.01608 (7)0.0155 (2)
H120.93700.13890.00020.019*
C131.04867 (12)0.19517 (11)0.05401 (8)0.0189 (3)
H131.09160.14100.06290.023*
C141.07830 (12)0.27478 (11)0.07873 (8)0.0193 (3)
H141.14170.27590.10430.023*
C151.01347 (12)0.35294 (10)0.06543 (8)0.0190 (3)
H151.03160.40740.08270.023*
C160.92198 (12)0.35140 (10)0.02680 (8)0.0171 (3)
H160.87970.40600.01790.021*
C170.64551 (12)0.25013 (10)0.02617 (8)0.0156 (2)
C180.53451 (12)0.26090 (10)0.00582 (8)0.0181 (3)
H180.53590.28330.04820.022*
C190.42312 (12)0.24021 (11)0.06130 (9)0.0224 (3)
H190.35090.24920.04470.027*
C200.41749 (13)0.20643 (11)0.14102 (9)0.0248 (3)
H200.34180.19210.17920.030*
C210.52392 (14)0.19396 (11)0.16378 (8)0.0248 (3)
H210.52110.17000.21810.030*
C220.63568 (13)0.21642 (10)0.10724 (8)0.0200 (3)
H20.70760.20860.12440.024*
C230.80202 (11)0.39532 (10)0.10867 (7)0.0144 (2)
C240.90731 (12)0.43503 (10)0.17312 (8)0.0195 (3)
H240.95990.39030.17910.023*
C250.93838 (13)0.53692 (11)0.22868 (8)0.0223 (3)
H251.01070.55990.27120.027*
C260.86385 (13)0.60503 (11)0.22215 (8)0.0215 (3)
H260.88410.67450.25990.026*
C270.75911 (13)0.56894 (10)0.15907 (8)0.0199 (3)
H270.70680.61410.15350.024*
C280.73019 (12)0.46676 (10)0.10378 (8)0.0166 (3)
H280.65860.44460.06090.020*
C290.77013 (11)0.18967 (10)0.08248 (7)0.0146 (2)
C300.87714 (12)0.17699 (10)0.12790 (8)0.0170 (3)
H300.95300.22290.13790.020*
C310.87737 (12)0.10107 (10)0.15866 (8)0.0182 (3)
H310.95230.09570.18820.022*
C320.76808 (13)0.03260 (10)0.14644 (8)0.0185 (3)
H320.76760.01990.16690.022*
C330.66014 (12)0.04320 (10)0.10369 (8)0.0186 (3)
H330.58450.00180.09540.022*
C340.66199 (12)0.11944 (10)0.07278 (8)0.0164 (2)
H340.58650.12440.04370.020*
B20.21218 (12)0.21890 (11)0.46170 (8)0.0132 (3)
C350.18977 (11)0.10369 (10)0.39032 (7)0.0146 (2)
C360.07262 (12)0.05578 (10)0.33620 (8)0.0162 (2)
H360.00830.09130.34210.019*
C370.04716 (13)0.04096 (11)0.27466 (8)0.0209 (3)
H370.03290.06950.23940.025*
C380.13855 (14)0.09602 (11)0.26452 (9)0.0263 (3)
H380.12180.16220.22280.032*
C390.25467 (14)0.05202 (11)0.31674 (9)0.0255 (3)
H390.31810.08860.31100.031*
C400.27898 (12)0.04579 (10)0.37778 (8)0.0190 (3)
H400.35960.07420.41230.023*
C410.09474 (11)0.21976 (9)0.49961 (7)0.0134 (2)
C420.02629 (11)0.29574 (10)0.50940 (8)0.0158 (2)
H420.04500.34850.49060.019*
C430.06912 (12)0.29718 (11)0.54603 (8)0.0213 (3)
H430.11410.34980.55100.026*
C440.09777 (12)0.22214 (11)0.57497 (8)0.0207 (3)
H440.16120.22360.60070.025*
C450.03243 (12)0.14465 (11)0.56592 (8)0.0198 (3)
H450.05120.09260.58540.024*
C460.06078 (12)0.14359 (10)0.52818 (8)0.0176 (3)
H460.10310.08910.52150.021*
C470.33983 (11)0.24479 (9)0.53140 (7)0.0143 (2)
C480.34464 (12)0.26164 (10)0.61014 (8)0.0172 (3)
H480.27040.25970.62530.021*
C490.45487 (13)0.28120 (11)0.66708 (8)0.0227 (3)
H490.45390.29240.71970.027*
C500.56528 (13)0.28439 (11)0.64765 (9)0.0243 (3)
H500.63970.29550.68590.029*
C510.56484 (12)0.27095 (10)0.57047 (9)0.0219 (3)
H510.63960.27380.55600.026*
C520.45479 (12)0.25341 (10)0.51484 (8)0.0172 (3)
H520.45710.24690.46330.021*
C530.21969 (11)0.31079 (10)0.42702 (7)0.0134 (2)
C540.15048 (11)0.29751 (10)0.35213 (7)0.0160 (2)
H540.10230.23040.31750.019*
C550.14934 (12)0.37874 (11)0.32625 (8)0.0183 (3)
H550.10130.36590.27490.022*
C560.21772 (12)0.47772 (10)0.37494 (8)0.0179 (3)
H560.21690.53300.35750.021*
C570.28783 (12)0.49490 (10)0.44999 (8)0.0183 (3)
H570.33520.56240.48440.022*
C580.28817 (12)0.41266 (10)0.47442 (8)0.0169 (3)
H580.33710.42600.52560.020*
O10.34685 (13)0.37036 (10)0.13799 (8)0.0436 (3)
C590.31258 (14)0.44161 (12)0.12440 (9)0.0257 (3)
C600.37217 (16)0.49196 (14)0.07953 (11)0.0353 (4)
H60A0.40420.56620.11190.053*
H60B0.31180.48270.03110.053*
H60C0.43980.46010.06610.053*
C610.20691 (17)0.47985 (18)0.15014 (11)0.0436 (5)
H61A0.13060.44080.10880.065*
H61B0.21780.55370.15990.065*
H61C0.20280.47020.19860.065*
O20.59749 (11)0.08463 (11)0.35934 (9)0.0449 (3)
C620.62729 (14)0.00823 (11)0.45296 (9)0.0259 (3)
H62A0.57880.05480.47850.039*
H62B0.70440.01730.49140.039*
H62C0.58080.06380.43260.039*
C630.65441 (13)0.03302 (11)0.38676 (9)0.0242 (3)
C640.75574 (14)0.00695 (13)0.35534 (9)0.0286 (3)
H64A0.75500.00380.30670.043*
H64B0.74390.08120.34430.043*
H64C0.83470.03040.39450.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0143 (5)0.0173 (5)0.0180 (5)0.0052 (4)0.0070 (4)0.0075 (4)
N20.0124 (5)0.0165 (5)0.0177 (5)0.0045 (4)0.0041 (4)0.0046 (4)
N30.0131 (5)0.0191 (5)0.0167 (5)0.0029 (4)0.0019 (4)0.0094 (4)
C10.0139 (6)0.0168 (6)0.0105 (5)0.0029 (5)0.0032 (4)0.0040 (5)
C20.0159 (6)0.0206 (6)0.0199 (6)0.0081 (5)0.0077 (5)0.0070 (5)
C30.0214 (7)0.0247 (7)0.0251 (7)0.0066 (5)0.0110 (6)0.0157 (6)
C40.0137 (6)0.0227 (7)0.0233 (7)0.0003 (5)0.0027 (5)0.0069 (6)
C50.0174 (6)0.0205 (7)0.0302 (8)0.0093 (5)0.0066 (6)0.0064 (6)
C60.0137 (6)0.0203 (6)0.0167 (6)0.0010 (5)0.0037 (5)0.0082 (5)
C70.0149 (6)0.0249 (7)0.0165 (6)0.0003 (5)0.0031 (5)0.0031 (5)
N4A0.0136 (11)0.0206 (6)0.0163 (9)0.0037 (5)0.0039 (5)0.0041 (6)
C8A0.0192 (8)0.0409 (14)0.0380 (11)0.0090 (9)0.0061 (8)0.0036 (10)
C9A0.0329 (10)0.0352 (12)0.0164 (8)0.0008 (9)0.0011 (7)0.0088 (8)
C10A0.0389 (11)0.0190 (8)0.0346 (10)0.0014 (7)0.0027 (8)0.0101 (8)
N4B0.0136 (11)0.0206 (6)0.0163 (9)0.0037 (5)0.0039 (5)0.0041 (6)
C8B0.0192 (8)0.0409 (14)0.0380 (11)0.0090 (9)0.0061 (8)0.0036 (10)
C9B0.0329 (10)0.0352 (12)0.0164 (8)0.0008 (9)0.0011 (7)0.0088 (8)
C10B0.0389 (11)0.0190 (8)0.0346 (10)0.0014 (7)0.0027 (8)0.0101 (8)
B10.0127 (6)0.0164 (6)0.0145 (6)0.0044 (5)0.0039 (5)0.0082 (5)
C110.0124 (5)0.0144 (6)0.0129 (6)0.0028 (4)0.0023 (5)0.0048 (5)
C120.0146 (6)0.0158 (6)0.0157 (6)0.0039 (5)0.0035 (5)0.0061 (5)
C130.0170 (6)0.0236 (7)0.0174 (6)0.0086 (5)0.0056 (5)0.0078 (5)
C140.0158 (6)0.0245 (7)0.0164 (6)0.0023 (5)0.0060 (5)0.0063 (5)
C150.0210 (6)0.0185 (6)0.0174 (6)0.0016 (5)0.0069 (5)0.0070 (5)
C160.0199 (6)0.0160 (6)0.0170 (6)0.0049 (5)0.0065 (5)0.0071 (5)
C170.0151 (6)0.0135 (6)0.0177 (6)0.0041 (5)0.0027 (5)0.0061 (5)
C180.0155 (6)0.0179 (6)0.0213 (6)0.0045 (5)0.0036 (5)0.0087 (5)
C190.0151 (6)0.0189 (6)0.0322 (8)0.0038 (5)0.0026 (6)0.0112 (6)
C200.0210 (7)0.0201 (7)0.0278 (7)0.0030 (5)0.0055 (6)0.0104 (6)
C210.0277 (7)0.0239 (7)0.0179 (7)0.0044 (6)0.0009 (6)0.0070 (6)
C220.0202 (6)0.0194 (6)0.0183 (6)0.0054 (5)0.0020 (5)0.0066 (5)
C230.0142 (6)0.0173 (6)0.0143 (6)0.0048 (5)0.0063 (5)0.0075 (5)
C240.0202 (6)0.0192 (6)0.0175 (6)0.0054 (5)0.0028 (5)0.0064 (5)
C250.0242 (7)0.0213 (7)0.0167 (6)0.0025 (5)0.0026 (5)0.0047 (5)
C260.0275 (7)0.0158 (6)0.0207 (7)0.0033 (5)0.0115 (6)0.0046 (5)
C270.0229 (7)0.0175 (6)0.0254 (7)0.0072 (5)0.0121 (6)0.0114 (5)
C280.0167 (6)0.0181 (6)0.0183 (6)0.0047 (5)0.0070 (5)0.0094 (5)
C290.0139 (6)0.0163 (6)0.0137 (6)0.0038 (5)0.0053 (5)0.0051 (5)
C300.0160 (6)0.0193 (6)0.0178 (6)0.0044 (5)0.0055 (5)0.0091 (5)
C310.0189 (6)0.0212 (6)0.0159 (6)0.0058 (5)0.0039 (5)0.0089 (5)
C320.0253 (7)0.0158 (6)0.0169 (6)0.0057 (5)0.0083 (5)0.0077 (5)
C330.0192 (6)0.0166 (6)0.0196 (6)0.0016 (5)0.0088 (5)0.0055 (5)
C340.0140 (6)0.0165 (6)0.0191 (6)0.0044 (5)0.0060 (5)0.0064 (5)
B20.0125 (6)0.0136 (6)0.0139 (6)0.0039 (5)0.0033 (5)0.0057 (5)
C350.0153 (6)0.0154 (6)0.0146 (6)0.0046 (5)0.0049 (5)0.0070 (5)
C360.0157 (6)0.0167 (6)0.0168 (6)0.0044 (5)0.0047 (5)0.0070 (5)
C370.0192 (6)0.0207 (7)0.0173 (6)0.0007 (5)0.0010 (5)0.0046 (5)
C380.0288 (8)0.0203 (7)0.0215 (7)0.0062 (6)0.0043 (6)0.0004 (6)
C390.0249 (7)0.0210 (7)0.0259 (7)0.0111 (6)0.0071 (6)0.0015 (6)
C400.0169 (6)0.0183 (6)0.0189 (6)0.0055 (5)0.0037 (5)0.0041 (5)
C410.0129 (6)0.0137 (6)0.0115 (6)0.0035 (4)0.0011 (4)0.0035 (5)
C420.0147 (6)0.0157 (6)0.0171 (6)0.0052 (5)0.0038 (5)0.0063 (5)
C430.0176 (6)0.0226 (7)0.0244 (7)0.0086 (5)0.0081 (5)0.0073 (6)
C440.0171 (6)0.0242 (7)0.0203 (7)0.0043 (5)0.0090 (5)0.0060 (5)
C450.0204 (6)0.0201 (6)0.0203 (6)0.0019 (5)0.0077 (5)0.0092 (5)
C460.0189 (6)0.0170 (6)0.0196 (6)0.0066 (5)0.0072 (5)0.0083 (5)
C470.0149 (6)0.0120 (5)0.0159 (6)0.0038 (4)0.0029 (5)0.0057 (5)
C480.0209 (6)0.0142 (6)0.0167 (6)0.0045 (5)0.0032 (5)0.0072 (5)
C490.0286 (7)0.0190 (6)0.0173 (6)0.0032 (5)0.0018 (6)0.0087 (5)
C500.0209 (7)0.0178 (6)0.0279 (7)0.0041 (5)0.0069 (6)0.0095 (6)
C510.0148 (6)0.0160 (6)0.0310 (8)0.0032 (5)0.0011 (6)0.0078 (6)
C520.0150 (6)0.0160 (6)0.0203 (6)0.0043 (5)0.0041 (5)0.0070 (5)
C530.0115 (5)0.0163 (6)0.0151 (6)0.0060 (4)0.0058 (5)0.0070 (5)
C540.0142 (6)0.0182 (6)0.0153 (6)0.0044 (5)0.0030 (5)0.0067 (5)
C550.0167 (6)0.0241 (7)0.0170 (6)0.0071 (5)0.0037 (5)0.0109 (5)
C560.0196 (6)0.0199 (6)0.0216 (7)0.0098 (5)0.0093 (5)0.0130 (5)
C570.0225 (6)0.0136 (6)0.0191 (6)0.0035 (5)0.0064 (5)0.0065 (5)
C580.0200 (6)0.0158 (6)0.0149 (6)0.0038 (5)0.0037 (5)0.0066 (5)
O10.0590 (8)0.0319 (6)0.0381 (7)0.0117 (6)0.0032 (6)0.0205 (6)
C590.0257 (7)0.0268 (7)0.0201 (7)0.0040 (6)0.0032 (6)0.0100 (6)
C600.0362 (9)0.0363 (9)0.0447 (10)0.0149 (7)0.0185 (8)0.0223 (8)
C610.0336 (9)0.0724 (14)0.0310 (9)0.0154 (9)0.0115 (7)0.0248 (9)
O20.0324 (6)0.0494 (8)0.0805 (10)0.0195 (6)0.0191 (6)0.0518 (8)
C620.0277 (7)0.0211 (7)0.0344 (8)0.0084 (6)0.0161 (6)0.0120 (6)
C630.0194 (7)0.0222 (7)0.0351 (8)0.0039 (5)0.0060 (6)0.0172 (6)
C640.0273 (8)0.0392 (9)0.0296 (8)0.0135 (7)0.0131 (6)0.0204 (7)
Geometric parameters (Å, º) top
N1—C11.3308 (16)C25—H250.9500
N1—C21.4668 (16)C26—C271.390 (2)
N1—C31.4674 (16)C26—H260.9500
N2—C11.3425 (16)C27—C281.3967 (19)
N2—C41.4609 (17)C27—H270.9500
N2—C51.4628 (17)C28—H280.9500
N3—C11.3508 (16)C29—C341.4120 (17)
N3—C61.4612 (16)C29—C301.4154 (18)
N3—H30.855 (19)C30—C311.3888 (18)
C2—H2A0.9800C30—H300.9500
C2—H2B0.9800C31—C321.3955 (19)
C2—H2C0.9800C31—H310.9500
C3—H3A0.9800C32—C331.3875 (19)
C3—H3B0.9800C32—H320.9500
C3—H3C0.9800C33—C341.3945 (18)
C4—H4A0.9800C33—H330.9500
C4—H4B0.9800C34—H340.9500
C4—H4C0.9800B2—C411.6457 (18)
C5—H5A0.9800B2—C531.6478 (18)
C5—H5B0.9800B2—C471.6496 (18)
C5—H5C0.9800B2—C351.6524 (18)
C6—C71.5286 (18)C35—C401.4001 (18)
C6—H6A0.9900C35—C361.4141 (18)
C6—H6B0.9900C36—C371.3917 (19)
C7—N4A1.504 (5)C36—H360.9500
C7—N4B1.55 (3)C37—C381.392 (2)
C7—H7A0.9900C37—H370.9500
C7—H7B0.9900C38—C391.388 (2)
N4A—C8A1.487 (3)C38—H380.9500
N4A—C10A1.501 (3)C39—C401.3989 (19)
N4A—C9A1.504 (3)C39—H390.9500
C8A—H8A10.9800C40—H400.9500
C8A—H8A20.9800C41—C421.3975 (17)
C8A—H8A30.9800C41—C461.4078 (17)
C9A—H9A10.9800C42—C431.4051 (18)
C9A—H9A20.9800C42—H420.9500
C9A—H9A30.9800C43—C441.385 (2)
C10A—H10A0.9800C43—H430.9500
C10A—H10B0.9800C44—C451.391 (2)
C10A—H10C0.9800C44—H440.9500
N4B—C8B1.464 (17)C45—C461.3970 (18)
N4B—C9B1.491 (17)C45—H450.9500
N4B—C10B1.508 (17)C46—H460.9500
C8B—H8B10.9800C47—C481.4060 (18)
C8B—H8B20.9800C47—C521.4119 (18)
C8B—H8B30.9800C48—C491.3997 (19)
C9B—H9B10.9800C48—H480.9500
C9B—H9B20.9800C49—C501.385 (2)
C9B—H9B30.9800C49—H490.9500
C10B—H10D0.9800C50—C511.398 (2)
C10B—H10E0.9800C50—H500.9500
C10B—H10F0.9800C51—C521.3916 (18)
B1—C171.6478 (18)C51—H510.9500
B1—C111.6525 (18)C52—H520.9500
B1—C231.6578 (19)C53—C541.4034 (17)
B1—C291.6588 (18)C53—C581.4088 (18)
C11—C121.4048 (17)C54—C551.3983 (18)
C11—C161.4113 (17)C54—H540.9500
C12—C131.3967 (18)C55—C561.3835 (19)
C12—H120.9500C55—H550.9500
C13—C141.3893 (19)C56—C571.3940 (19)
C13—H130.9500C56—H560.9500
C14—C151.393 (2)C57—C581.3940 (18)
C14—H140.9500C57—H570.9500
C15—C161.3941 (18)C58—H580.9500
C15—H150.9500O1—C591.2185 (19)
C16—H160.9500C59—C601.488 (2)
C17—C221.4059 (19)C59—C611.492 (2)
C17—C181.4124 (18)C60—H60A0.9800
C18—C191.3927 (19)C60—H60B0.9800
C18—H180.9500C60—H60C0.9800
C19—C201.392 (2)C61—H61A0.9800
C19—H190.9500C61—H61B0.9800
C20—C211.385 (2)C61—H61C0.9800
C20—H200.9500O2—C631.2177 (18)
C21—C221.4012 (19)C62—C631.488 (2)
C21—H210.9500C62—H62A0.9800
C22—H20.9500C62—H62B0.9800
C23—C281.4027 (18)C62—H62C0.9800
C23—C241.4058 (18)C63—C641.497 (2)
C24—C251.3941 (19)C64—H64A0.9800
C24—H240.9500C64—H64B0.9800
C25—C261.392 (2)C64—H64C0.9800
C1—N1—C2122.30 (11)C25—C24—C23123.20 (13)
C1—N1—C3122.05 (11)C25—C24—H24118.4
C2—N1—C3115.58 (10)C23—C24—H24118.4
C1—N2—C4122.22 (11)C26—C25—C24120.24 (13)
C1—N2—C5121.68 (11)C26—C25—H25119.9
C4—N2—C5115.46 (11)C24—C25—H25119.9
C1—N3—C6125.43 (11)C27—C26—C25118.37 (12)
C1—N3—H3118.1 (12)C27—C26—H26120.8
C6—N3—H3115.5 (12)C25—C26—H26120.8
N1—C1—N2120.62 (11)C26—C27—C28120.43 (13)
N1—C1—N3121.02 (11)C26—C27—H27119.8
N2—C1—N3118.36 (12)C28—C27—H27119.8
N1—C2—H2A109.5C27—C28—C23123.01 (12)
N1—C2—H2B109.5C27—C28—H28118.5
H2A—C2—H2B109.5C23—C28—H28118.5
N1—C2—H2C109.5C34—C29—C30113.77 (11)
H2A—C2—H2C109.5C34—C29—B1124.20 (11)
H2B—C2—H2C109.5C30—C29—B1121.96 (11)
N1—C3—H3A109.5C31—C30—C29123.60 (12)
N1—C3—H3B109.5C31—C30—H30118.2
H3A—C3—H3B109.5C29—C30—H30118.2
N1—C3—H3C109.5C30—C31—C32120.34 (12)
H3A—C3—H3C109.5C30—C31—H31119.8
H3B—C3—H3C109.5C32—C31—H31119.8
N2—C4—H4A109.5C33—C32—C31118.33 (12)
N2—C4—H4B109.5C33—C32—H32120.8
H4A—C4—H4B109.5C31—C32—H32120.8
N2—C4—H4C109.5C32—C33—C34120.45 (12)
H4A—C4—H4C109.5C32—C33—H33119.8
H4B—C4—H4C109.5C34—C33—H33119.8
N2—C5—H5A109.5C33—C34—C29123.50 (12)
N2—C5—H5B109.5C33—C34—H34118.2
H5A—C5—H5B109.5C29—C34—H34118.2
N2—C5—H5C109.5C41—B2—C53108.14 (10)
H5A—C5—H5C109.5C41—B2—C47109.45 (10)
H5B—C5—H5C109.5C53—B2—C47108.60 (10)
N3—C6—C7110.06 (10)C41—B2—C35108.30 (10)
N3—C6—H6A109.6C53—B2—C35110.78 (10)
C7—C6—H6A109.6C47—B2—C35111.51 (10)
N3—C6—H6B109.6C40—C35—C36114.79 (11)
C7—C6—H6B109.6C40—C35—B2125.26 (11)
H6A—C6—H6B108.2C36—C35—B2119.95 (11)
N4A—C7—C6114.75 (14)C37—C36—C35123.07 (12)
C6—C7—N4B108.6 (6)C37—C36—H36118.5
N4A—C7—H7A108.6C35—C36—H36118.5
C6—C7—H7A108.6C36—C37—C38120.22 (12)
N4A—C7—H7B108.6C36—C37—H37119.9
C6—C7—H7B108.6C38—C37—H37119.9
H7A—C7—H7B107.6C39—C38—C37118.52 (13)
C8A—N4A—C10A110.4 (3)C39—C38—H38120.7
C8A—N4A—C7112.2 (2)C37—C38—H38120.7
C10A—N4A—C7108.6 (3)C38—C39—C40120.50 (13)
C8A—N4A—C9A110.0 (3)C38—C39—H39119.7
C10A—N4A—C9A107.2 (2)C40—C39—H39119.7
C7—N4A—C9A108.3 (2)C39—C40—C35122.89 (12)
N4A—C8A—H8A1109.5C39—C40—H40118.6
N4A—C8A—H8A2109.5C35—C40—H40118.6
H8A1—C8A—H8A2109.5C42—C41—C46115.46 (11)
N4A—C8A—H8A3109.5C42—C41—B2124.15 (11)
H8A1—C8A—H8A3109.5C46—C41—B2120.33 (11)
H8A2—C8A—H8A3109.5C41—C42—C43122.56 (12)
N4A—C9A—H9A1109.5C41—C42—H42118.7
N4A—C9A—H9A2109.5C43—C42—H42118.7
H9A1—C9A—H9A2109.5C44—C43—C42120.17 (12)
N4A—C9A—H9A3109.5C44—C43—H43119.9
H9A1—C9A—H9A3109.5C42—C43—H43119.9
H9A2—C9A—H9A3109.5C43—C44—C45119.10 (12)
N4A—C10A—H10A109.5C43—C44—H44120.5
N4A—C10A—H10B109.5C45—C44—H44120.5
H10A—C10A—H10B109.5C44—C45—C46119.87 (12)
N4A—C10A—H10C109.5C44—C45—H45120.1
H10A—C10A—H10C109.5C46—C45—H45120.1
H10B—C10A—H10C109.5C45—C46—C41122.82 (12)
C8B—N4B—C9B111.1 (16)C45—C46—H46118.6
C8B—N4B—C10B111.3 (16)C41—C46—H46118.6
C9B—N4B—C10B105.4 (14)C48—C47—C52115.03 (11)
C8B—N4B—C7106.7 (14)C48—C47—B2124.28 (11)
C9B—N4B—C7105.0 (13)C52—C47—B2120.68 (11)
C10B—N4B—C7117.2 (15)C49—C48—C47122.40 (13)
N4B—C8B—H8B1109.5C49—C48—H48118.8
N4B—C8B—H8B2109.5C47—C48—H48118.8
H8B1—C8B—H8B2109.5C50—C49—C48120.80 (13)
N4B—C8B—H8B3109.5C50—C49—H49119.6
H8B1—C8B—H8B3109.5C48—C49—H49119.6
H8B2—C8B—H8B3109.5C49—C50—C51118.56 (12)
N4B—C9B—H9B1109.5C49—C50—H50120.7
N4B—C9B—H9B2109.5C51—C50—H50120.7
H9B1—C9B—H9B2109.5C52—C51—C50119.99 (13)
N4B—C9B—H9B3109.5C52—C51—H51120.0
H9B1—C9B—H9B3109.5C50—C51—H51120.0
H9B2—C9B—H9B3109.5C51—C52—C47123.11 (13)
N4B—C10B—H10D109.5C51—C52—H52118.4
N4B—C10B—H10E109.5C47—C52—H52118.4
H10D—C10B—H10E109.5C54—C53—C58114.75 (11)
N4B—C10B—H10F109.5C54—C53—B2123.50 (11)
H10D—C10B—H10F109.5C58—C53—B2121.47 (11)
H10E—C10B—H10F109.5C55—C54—C53122.84 (12)
C17—B1—C11108.93 (10)C55—C54—H54118.6
C17—B1—C23109.99 (10)C53—C54—H54118.6
C11—B1—C23106.64 (10)C56—C55—C54120.43 (12)
C17—B1—C29109.94 (10)C56—C55—H55119.8
C11—B1—C29110.37 (10)C54—C55—H55119.8
C23—B1—C29110.91 (10)C55—C56—C57118.89 (12)
C12—C11—C16114.93 (11)C55—C56—H56120.6
C12—C11—B1126.24 (11)C57—C56—H56120.6
C16—C11—B1118.76 (11)C56—C57—C58119.72 (12)
C13—C12—C11123.01 (12)C56—C57—H57120.1
C13—C12—H12118.5C58—C57—H57120.1
C11—C12—H12118.5C57—C58—C53123.36 (12)
C14—C13—C12120.17 (12)C57—C58—H58118.3
C14—C13—H13119.9C53—C58—H58118.3
C12—C13—H13119.9O1—C59—C60121.36 (16)
C13—C14—C15118.84 (12)O1—C59—C61121.27 (16)
C13—C14—H14120.6C60—C59—C61117.35 (14)
C15—C14—H14120.6C59—C60—H60A109.5
C14—C15—C16120.11 (12)C59—C60—H60B109.5
C14—C15—H15119.9H60A—C60—H60B109.5
C16—C15—H15119.9C59—C60—H60C109.5
C15—C16—C11122.93 (12)H60A—C60—H60C109.5
C15—C16—H16118.5H60B—C60—H60C109.5
C11—C16—H16118.5C59—C61—H61A109.5
C22—C17—C18114.99 (12)C59—C61—H61B109.5
C22—C17—B1123.53 (11)H61A—C61—H61B109.5
C18—C17—B1121.48 (11)C59—C61—H61C109.5
C19—C18—C17123.04 (13)H61A—C61—H61C109.5
C19—C18—H18118.5H61B—C61—H61C109.5
C17—C18—H18118.5C63—C62—H62A109.5
C20—C19—C18120.03 (13)C63—C62—H62B109.5
C20—C19—H19120.0H62A—C62—H62B109.5
C18—C19—H19120.0C63—C62—H62C109.5
C21—C20—C19118.94 (13)H62A—C62—H62C109.5
C21—C20—H20120.5H62B—C62—H62C109.5
C19—C20—H20120.5O2—C63—C62121.64 (14)
C20—C21—C22120.42 (13)O2—C63—C64120.87 (14)
C20—C21—H21119.8C62—C63—C64117.48 (12)
C22—C21—H21119.8C63—C64—H64A109.5
C21—C22—C17122.56 (13)C63—C64—H64B109.5
C21—C22—H2118.7H64A—C64—H64B109.5
C17—C22—H2118.7C63—C64—H64C109.5
C28—C23—C24114.74 (12)H64A—C64—H64C109.5
C28—C23—B1124.38 (11)H64B—C64—H64C109.5
C24—C23—B1120.69 (11)
C2—N1—C1—N2151.36 (12)C23—B1—C29—C3073.78 (15)
C3—N1—C1—N231.64 (18)C34—C29—C30—C311.59 (19)
C2—N1—C1—N329.01 (18)B1—C29—C30—C31175.45 (12)
C3—N1—C1—N3147.99 (12)C29—C30—C31—C320.8 (2)
C4—N2—C1—N134.13 (18)C30—C31—C32—C330.6 (2)
C5—N2—C1—N1155.46 (12)C31—C32—C33—C341.1 (2)
C4—N2—C1—N3146.24 (12)C32—C33—C34—C290.2 (2)
C5—N2—C1—N324.18 (18)C30—C29—C34—C331.07 (19)
C6—N3—C1—N135.61 (19)B1—C29—C34—C33175.89 (12)
C6—N3—C1—N2144.03 (13)C41—B2—C35—C40136.36 (12)
C1—N3—C6—C746.52 (17)C53—B2—C35—C40105.20 (14)
N3—C6—C7—N4A162.38 (16)C47—B2—C35—C4015.88 (17)
N3—C6—C7—N4B166.3 (7)C41—B2—C35—C3643.17 (15)
C6—C7—N4A—C8A47.0 (3)C53—B2—C35—C3675.27 (14)
C6—C7—N4A—C10A75.3 (2)C47—B2—C35—C36163.65 (11)
C6—C7—N4A—C9A168.60 (17)C40—C35—C36—C370.51 (19)
C6—C7—N4B—C8B80.1 (11)B2—C35—C36—C37179.91 (12)
C6—C7—N4B—C9B161.9 (9)C35—C36—C37—C380.8 (2)
C6—C7—N4B—C10B45.3 (13)C36—C37—C38—C390.3 (2)
C17—B1—C11—C12107.20 (13)C37—C38—C39—C400.4 (2)
C23—B1—C11—C12134.13 (12)C38—C39—C40—C350.6 (2)
C29—B1—C11—C1213.59 (17)C36—C35—C40—C390.18 (19)
C17—B1—C11—C1669.79 (14)B2—C35—C40—C39179.37 (13)
C23—B1—C11—C1648.87 (14)C53—B2—C41—C428.02 (16)
C29—B1—C11—C16169.42 (11)C47—B2—C41—C42110.12 (13)
C16—C11—C12—C130.78 (18)C35—B2—C41—C42128.12 (12)
B1—C11—C12—C13177.87 (12)C53—B2—C41—C46175.05 (11)
C11—C12—C13—C140.5 (2)C47—B2—C41—C4666.81 (14)
C12—C13—C14—C150.41 (19)C35—B2—C41—C4654.95 (14)
C13—C14—C15—C161.02 (19)C46—C41—C42—C430.71 (18)
C14—C15—C16—C110.7 (2)B2—C41—C42—C43176.35 (12)
C12—C11—C16—C150.15 (18)C41—C42—C43—C440.8 (2)
B1—C11—C16—C15177.47 (12)C42—C43—C44—C451.2 (2)
C11—B1—C17—C228.33 (16)C43—C44—C45—C460.1 (2)
C23—B1—C17—C22124.87 (13)C44—C45—C46—C411.4 (2)
C29—B1—C17—C22112.72 (13)C42—C41—C46—C451.80 (19)
C11—B1—C17—C18171.63 (11)B2—C41—C46—C45175.39 (12)
C23—B1—C17—C1855.09 (15)C41—B2—C47—C481.73 (16)
C29—B1—C17—C1867.32 (15)C53—B2—C47—C48119.59 (13)
C22—C17—C18—C190.17 (19)C35—B2—C47—C48118.07 (13)
B1—C17—C18—C19179.80 (12)C41—B2—C47—C52177.06 (11)
C17—C18—C19—C200.5 (2)C53—B2—C47—C5259.21 (15)
C18—C19—C20—C210.0 (2)C35—B2—C47—C5263.13 (15)
C19—C20—C21—C220.9 (2)C52—C47—C48—C492.56 (18)
C20—C21—C22—C171.3 (2)B2—C47—C48—C49178.59 (12)
C18—C17—C22—C210.73 (19)C47—C48—C49—C500.2 (2)
B1—C17—C22—C21179.31 (12)C48—C49—C50—C512.0 (2)
C17—B1—C23—C285.93 (16)C49—C50—C51—C520.9 (2)
C11—B1—C23—C28112.04 (13)C50—C51—C52—C472.2 (2)
C29—B1—C23—C28127.76 (12)C48—C47—C52—C513.77 (19)
C17—B1—C23—C24179.36 (11)B2—C47—C52—C51177.33 (12)
C11—B1—C23—C2462.67 (14)C41—B2—C53—C5483.82 (14)
C29—B1—C23—C2457.53 (15)C47—B2—C53—C54157.49 (11)
C28—C23—C24—C250.61 (19)C35—B2—C53—C5434.71 (16)
B1—C23—C24—C25175.80 (12)C41—B2—C53—C5889.73 (13)
C23—C24—C25—C260.1 (2)C47—B2—C53—C5828.96 (16)
C24—C25—C26—C270.3 (2)C35—B2—C53—C58151.74 (11)
C25—C26—C27—C280.1 (2)C58—C53—C54—C550.06 (18)
C26—C27—C28—C230.9 (2)B2—C53—C54—C55174.00 (12)
C24—C23—C28—C271.07 (18)C53—C54—C55—C560.3 (2)
B1—C23—C28—C27176.05 (12)C54—C55—C56—C570.2 (2)
C17—B1—C29—C3412.37 (17)C55—C56—C57—C580.2 (2)
C11—B1—C29—C34132.55 (12)C56—C57—C58—C530.5 (2)
C23—B1—C29—C34109.49 (13)C54—C53—C58—C570.32 (19)
C17—B1—C29—C30164.36 (11)B2—C53—C58—C57173.75 (12)
C11—B1—C29—C3044.17 (16)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C23–C28, C29–C34, C35–C40 and C53–C58 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N3—H3···O20.86 (2)2.07 (2)2.777 (2)140 (2)
C9A—H9A3···O10.982.483.329 (2)144
C8B—H8B1···O10.982.203.131 (2)158
C7—H7A···O10.992.433.353 (2)155
C3—H3C···Cg10.982.683.306 (2)122
C9A—H9A1···Cg2i0.983.113.612 (2)130
C9B—H9B2···Cg2i0.982.953.409 (2)110
C10B—H10E···Cg30.982.483.337 (2)146
C2—H2C···Cg40.982.983.543 (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.

References

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