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ISSN: 2414-3146

N,N,N′,N′,N′′-Penta­methyl-N′′-[2-(tri­methyl­aza­n­ium­yl)eth­yl]guanidinium bis­­(tetra­phenyl­borate) acetone monosolvate

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 26 January 2016; accepted 6 February 2016; online 13 February 2016)

The asymmetric unit of the title solvated salt, C11H28N42+·2C24H20B·C3H6O, comprises two cations, four tetra­phenyl­borate anions and two acetone mol­ecules. One cation shows an orientational disorder at the CN3 moiety and two sets of N-atom positions were found related by a 60° rotation, with a refined occupancy ratio of 0.935 (1):0.065 (1). The respective nitro­gen-bonded –CH2 and –CH3 groups are included in the disorder model. The C—N bond lengths in the central CN3 units of both guanidinium ions range between 1.3329 (17) and 1.364 (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 one positive charge is delocalized in the CN3 plane. The C—N bond lengths in the terminal tri­methyl­ammonium groups have values close to a typical single bond, and the second positive charge is localized there. In the crystal, the guanidinium ions are connected by C—H⋯O hydrogen bonds with the acetone mol­ecules. C—H⋯π inter­actions are present between the guanidinium and acetone hydrogen 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 such as N′′-[2-(di­methyl­amino)­eth­yl]-N,N,N′,N′-tetra­methyl­guanidine (Tiritiris & Kantlehner, 2012b[Tiritiris, I. & Kantlehner, W. (2012b). Z. Naturforsch. Teil B, 67, 685-698.]) are well known in the literature. Electrophiles can attack at both the imine nitro­gen of the guanidine function as well as on the nitro­gen atom of the (di­methyl­amino)­propyl group. By alkyl­ation with two equivalents of dimethyl sulfate, a permethyl­ated waxy guanidinium bis­(methyl sulfate) salt was obtained. After anion exchange with sodium tetra­phenyl­borate and crystallization from acetone, the title compound emerged. The asymmetric unit comprises two cations, four tetra­phenyl­borate anions and two acetone mol­ecules (Fig. 1[link]). Cation I is not disordered. In contrast, cation II shows an orientational disorder and two sets of N positions were found related by a 60° rotation, with an occupancy ratio of 0.935 (1):0.065 (1). The respective nitro­gen bonded –CH2 and –CH3 groups are included in the disorder model (Fig. 2[link]). A similar type of disorder at the CN3 moiety has been observed in the crystal structures of salts containing the N,N,N′,N′,N′′,N′′-hexa­methyl­guanidinium ion [see, for example: cyanate salt (Tiritiris & Kantlehner, 2015a[Tiritiris, I. & Kantlehner, W. (2015a). Acta Cryst. E71, o1076-o1077.]); chloride salt (Oelkers & Sundermeyer, 2011[Oelkers, B. & Sundermeyer, J. (2011). Green Chem. 13, 608-618.])]. In the title salt, the central C—N bond lengths of both cations are in a range from 1.3329 (17) to 1.364 (16) Å, indicating partial double-bond character for all. The N—C1—N and N—C12—N angles range from 117.4 (17) to 120.76 (12)°, indicating that the carbon centres C1 and C12 show nearly ideal trigonal–planar environments. One of the two positive charges is completely delocalized in every CN3 plane, while the second positive charge is localized in the terminal tri­methyl­ammonium group. The N—C bond lengths in the [NMe3]+ unit have values close to a typical single bond [d(N—C) = 1.4903 (16)–1.5114 (16) Å]. The crystal structure analysis reveals that the C—N and C—C bond lengths in both cations are in very good agreement with the values obtained for the cation in N,N,N′,N′,N′′-penta­methyl-N′′-[3-(tri­methyl­aza­nium­yl)prop­yl]guanidinium bis­(tetra­phenyl­borate) (Tiritiris, 2013a[Tiritiris, I. (2013a). Acta Cryst. E69, o292.]). The bond lengths and angles in all four tetra­phenyl­borate ions are in good agreement with the data from the crystal structure analysis of alkali metal tetra­phenyl­borates (Behrens et al., 2012a[Behrens, U., Hoffmann, F. & Olbrich, F. (2012a). Organometallics, 31, 905-913.]).

[Figure 1]
Figure 1
The structure of the title compound, with displacement ellipsoids at the 50% probability level. All H atoms have been omitted for clarity. Only the major orientation of the disordered cation II is shown.
[Figure 2]
Figure 2
The structure of the orientationally disordered cation II. The N and C atoms are disordered between the opaque and dark positions. All H atoms have been omitted for clarity.

In the crystal, the guanidinium ions are connected by C—H⋯O hydrogen bonds (Fig. 3[link]) with the acetone mol­ecules (Table 1[link]). C—H⋯π inter­actions between the hydrogen atoms of the –N(CH3) and –CH2 groups of the guanidinium ion and and the phenyl carbon atoms of the tetra­phenyl­borate ions are present (Table 1[link]). The acetone mol­ecules are involved in the C—H⋯π hydrogen bonding too, inter­acting with the hydrogen atoms of their methyl groups (Table 1[link]). This leads to the formation of a two-dimensional supra­molecular pattern along the bc plane (Fig. 4[link]). Such C—H⋯π inter­actions have been also observed in N,N,N′,N′,N′′-penta­methyl-N′′-[3-(tri­methyl­aza­nium­yl)prop­yl]guanidinium bis­(tetra­phenyl­borate) (Tiritiris, 2013a[Tiritiris, I. (2013a). Acta Cryst. E69, o292.]) 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, °)

The ring centroids are defined as follows: Cg1 = C53–C58, Cg2 = C65–C70, Cg3 = C71–C76, Cg4 = C89–C94, Cg5 = C95–C100, Cg6 = C29–C34, Cg7 = C41–C46, Cg8 = C101–C106, Cg9 = C107–C112 and Cg10 = C113–C118.

D—H⋯A D—H H⋯A DA D—H⋯A
C13B—H13E⋯O1 0.98 2.61 3.513 (2) 153
C17A—H17C⋯O1 0.98 2.41 3.369 (2) 167
C19—H19A⋯O1 0.99 2.37 3.290 (2) 154
C20—H20C⋯O1 0.98 2.46 3.323 (2) 147
C6—H6A⋯O2 0.98 2.50 3.467 (2) 170
C8—H8B⋯O2 0.99 2.55 3.449 (2) 152
C9—H9B⋯O2 0.98 2.52 3.417 (2) 152
C4—H4BCg1 0.98 3.02 3.881 (2) 146
C21—H21BCg1 0.98 2.74 3.713 (2) 171
C3—H3CCg2i 0.98 2.88 3.739 (2) 147
C13A—H13ACg3 0.98 2.75 3.587 (2) 144
C27—H27CCg3ii 0.98 2.94 3.629 (2) 128
C28—H28BCg4ii 0.98 2.84 3.554 (2) 130
C6—H6BCg5iii 0.98 2.67 3.614 (2) 162
C8—H8ACg6 0.99 2.93 3.854 (2) 155
C4—H4CCg7 0.98 2.76 3.669 (2) 154
C24—H24BCg8 0.98 3.05 3.681 (2) 124
C18A—H18ACg9iv 0.99 2.71 3.512 (2) 139
C18B—H18CCg9iv 0.99 2.87 3.662 (2) 138
C25—H25CCg10v 0.98 2.68 3.653 (2) 175
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+1, -z+1; (v) x-1, y-1, z.
[Figure 3]
Figure 3
C—H⋯O hydrogen bonds (black dashed lines) between the guanidinium ions and the acetone mol­ecules. H atoms not involved in the hydrogen bonding have been omitted. Both orientations of the disordered cation II are shown.
[Figure 4]
Figure 4
C—H⋯π inter­actions (brown dashed lines) between the H atoms of the guanidinium ions, the acetone mol­ecules and the phenyl rings (centroids) of the tetra­phenyl­borate ions (viewed along bc). Only the major orientation of the disordered cation II is shown.

Synthesis and crystallization

The title compound was obtained by reaction of N′′-[2-(di­methyl­amino)­eth­yl]-N,N,N′,N′-tetra­methyl­guanidine (Tiritiris & Kantlehner, 2012b[Tiritiris, I. & Kantlehner, W. (2012b). Z. Naturforsch. Teil B, 67, 685-698.]) with two equivalents of dimethyl sulfate in aceto­nitrile at room temperature. After evaporation of the solvent, the crude N,N,N′,N′,N′′-penta­methyl-N′′-[2-(tri­methyl­aza­nium­yl)eth­yl]guanidinium bis­(methyl sulfate) (I) was washed with di­ethyl­ether and dried in vacuo. 1.01 g (2.3 mmol) of (I) was dissolved in 20 ml aceto­nitrile and 1.57 g (4.6 mmol) of sodium tetra­phenyl­borate in 20 ml aceto­nitrile was added. After stirring for one h at room temperature, the precipitated sodium methyl sulfate was filtered off. The title compound crystallized from a saturated acetone solution after several days at 273 K, forming colorless single crystals. Yield: 1.36 g (70%).

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]. Atoms C12–C18 and N5–N7 of one cation (cation II) are disordered over two sets of sites (C12A/C12B–C18A/C18B and N5A/N5B–N7A/N7B) with refined occupancies of 0.935 (1):0.065 (1). They were constrained to have identical anisotropic displacement parameters. The major and minor disordered components were each restrained to have similar geometries.

Table 2
Experimental details

Crystal data
Chemical formula C11H28N4·2(C24H20B)·C3H6O
Mr 912.87
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 14.1885 (5), 17.5801 (7), 22.2543 (9)
α, β, γ (°) 72.911 (5), 86.243 (6), 80.123 (6)
V3) 5226.6 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.35 × 0.25 × 0.10
 
Data collection
Diffractometer Bruker–Nonius KappaCCD
Absorption correction
No. of measured, independent and observed [I > 2σ(I)] reflections 50000, 25738, 19692
Rint 0.028
(sin θ/λ)max−1) 0.666
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.109, 1.03
No. of reflections 25738
No. of parameters 1299
No. of restraints 21
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.42, −0.25
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, 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',N''-pentamethyl-N''- [2-(trimethylazaniumyl)ethyl]guanidinium bis(tetraphenylborate) acetone monosolvate top
Crystal data top
C11H28N4·2(C24H20B)·C3H6OZ = 4
Mr = 912.87F(000) = 1968
Triclinic, P1Dx = 1.160 Mg m3
a = 14.1885 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.5801 (7) ÅCell parameters from 25414 reflections
c = 22.2543 (9) Åθ = 0.4–28.3°
α = 72.911 (5)°µ = 0.07 mm1
β = 86.243 (6)°T = 100 K
γ = 80.123 (6)°Block, colorless
V = 5226.6 (4) Å30.35 × 0.25 × 0.10 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
19692 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 28.3°, θmin = 1.3°
φ scans, and ω scansh = 1818
50000 measured reflectionsk = 2323
25738 independent reflectionsl = 2929
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.035P)2 + 2.6221P]
where P = (Fo2 + 2Fc2)/3
25738 reflections(Δ/σ)max < 0.001
1299 parametersΔρmax = 0.42 e Å3
21 restraintsΔρmin = 0.25 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)
N10.82487 (8)0.57886 (7)0.09708 (5)0.0210 (2)
N20.66238 (8)0.57289 (7)0.10053 (5)0.0221 (2)
N30.71391 (8)0.69638 (6)0.08244 (5)0.0190 (2)
N40.64058 (8)0.84798 (6)0.16732 (5)0.0206 (2)
C10.73409 (9)0.61530 (7)0.09380 (6)0.0176 (2)
C20.90111 (10)0.61008 (9)0.11925 (7)0.0272 (3)
H2A0.93870.63710.08320.041*
H2B0.94290.56540.14740.041*
H2C0.87280.64870.14200.041*
C30.85562 (12)0.50601 (9)0.07669 (7)0.0290 (3)
H3A0.86610.45880.11370.044*
H3B0.91530.51100.05210.044*
H3C0.80600.49970.05070.044*
C40.66930 (12)0.48963 (8)0.14116 (7)0.0288 (3)
H4A0.68500.45230.11550.043*
H4B0.60800.48170.16310.043*
H4C0.71960.47920.17200.043*
C50.57415 (11)0.60457 (10)0.06484 (8)0.0319 (3)
H5A0.57960.65730.03520.048*
H5B0.52010.61030.09380.048*
H5C0.56360.56730.04160.048*
C60.77106 (10)0.74951 (8)0.03749 (6)0.0233 (3)
H6A0.81210.77080.06030.035*
H6B0.72850.79430.01010.035*
H6C0.81090.71910.01200.035*
C70.63600 (9)0.73577 (8)0.11471 (6)0.0214 (3)
H7A0.59050.69800.13340.026*
H7B0.60100.78350.08410.026*
C80.67607 (10)0.76210 (7)0.16664 (6)0.0200 (3)
H8A0.66020.72560.20790.024*
H8B0.74670.75480.16220.024*
C90.67268 (11)0.90746 (8)0.10968 (7)0.0262 (3)
H9A0.64410.90210.07250.039*
H9B0.74260.89690.10580.039*
H9C0.65230.96220.11300.039*
C100.68387 (14)0.85863 (10)0.22370 (8)0.0406 (4)
H10A0.66390.91410.22550.061*
H10B0.75380.84740.22030.061*
H10C0.66210.82120.26200.061*
C110.53426 (11)0.86399 (9)0.17301 (8)0.0336 (4)
H11A0.51370.91920.17540.050*
H11B0.51320.82590.21120.050*
H11C0.50590.85740.13620.050*
N80.38823 (7)0.17506 (6)0.34383 (5)0.0159 (2)
C12A0.21387 (14)0.37260 (11)0.42126 (16)0.0189 (4)0.9346 (13)
N5A0.28056 (9)0.41857 (7)0.41886 (6)0.0228 (3)0.9346 (13)
N6A0.12393 (9)0.40661 (8)0.40406 (6)0.0242 (3)0.9346 (13)
N7A0.23556 (8)0.29141 (7)0.44257 (6)0.0196 (3)0.9346 (13)
C13A0.35642 (12)0.39696 (10)0.46513 (8)0.0256 (4)0.9346 (13)
H13A0.41840.38550.44470.038*0.9346 (13)
H13B0.34500.34900.49890.038*0.9346 (13)
H13C0.35680.44190.48280.038*0.9346 (13)
C14A0.28006 (16)0.49709 (14)0.37137 (8)0.0282 (5)0.9346 (13)
H14A0.34510.50180.35460.042*0.9346 (13)
H14B0.25720.54040.39080.042*0.9346 (13)
H14C0.23750.50140.33710.042*0.9346 (13)
C15A0.07899 (14)0.48276 (10)0.41545 (8)0.0332 (4)0.9346 (13)
H15A0.01620.47660.43560.050*0.9346 (13)
H15B0.07120.52530.37540.050*0.9346 (13)
H15C0.11950.49730.44300.050*0.9346 (13)
C16A0.0642 (3)0.3705 (3)0.3723 (2)0.0315 (5)0.9346 (13)
H16A0.10190.32260.36360.047*0.9346 (13)
H16B0.04150.40970.33270.047*0.9346 (13)
H16C0.00920.35500.39940.047*0.9346 (13)
C17A0.16544 (12)0.23986 (10)0.47681 (7)0.0237 (3)0.9346 (13)
H17A0.10820.27380.48720.036*0.9346 (13)
H17B0.19400.20260.51560.036*0.9346 (13)
H17C0.14770.20900.45030.036*0.9346 (13)
C18A0.32576 (12)0.24767 (10)0.42601 (7)0.0201 (4)0.9346 (13)
H18A0.33940.19350.45660.024*0.9346 (13)
H18B0.37890.27720.42680.024*0.9346 (13)
C12B0.2131 (15)0.3729 (11)0.426 (2)0.0189 (4)0.0654 (13)
N5B0.1439 (11)0.3299 (9)0.4250 (7)0.0228 (3)0.0654 (13)
N6B0.1950 (11)0.4530 (9)0.3979 (8)0.0242 (3)0.0654 (13)
N7B0.3051 (10)0.3351 (9)0.4381 (8)0.0196 (3)0.0654 (13)
C13B0.1249 (19)0.2587 (13)0.4773 (10)0.0237 (3)0.0654 (13)
H13D0.17340.24640.50960.036*0.0654 (13)
H13E0.12740.21220.46110.036*0.0654 (13)
H13F0.06130.27060.49560.036*0.0654 (13)
C14B0.066 (5)0.361 (5)0.379 (3)0.0315 (5)0.0654 (13)
H14D0.03870.41580.37890.047*0.0654 (13)
H14E0.01670.32620.39100.047*0.0654 (13)
H14F0.09190.36040.33730.047*0.0654 (13)
C15B0.1186 (18)0.5088 (14)0.4165 (12)0.0332 (4)0.0654 (13)
H15D0.08500.47960.45370.050*0.0654 (13)
H15E0.07340.53310.38190.050*0.0654 (13)
H15F0.14600.55130.42620.050*0.0654 (13)
C16B0.267 (2)0.497 (2)0.3580 (16)0.0282 (5)0.0654 (13)
H16D0.28500.53570.37780.042*0.0654 (13)
H16E0.24050.52650.31650.042*0.0654 (13)
H16F0.32420.45900.35330.042*0.0654 (13)
C17B0.3706 (19)0.3667 (15)0.4709 (14)0.0256 (4)0.0654 (13)
H17D0.41780.32210.49430.038*0.0654 (13)
H17E0.33360.39290.50020.038*0.0654 (13)
H17F0.40370.40600.43990.038*0.0654 (13)
C18B0.341 (2)0.2618 (15)0.4187 (10)0.0201 (4)0.0654 (13)
H18C0.32670.21650.45480.024*0.0654 (13)
H18D0.41170.25800.41720.024*0.0654 (13)
C190.31651 (9)0.24013 (8)0.35999 (6)0.0186 (3)
H19A0.25140.22930.35580.022*
H19B0.32340.29240.32900.022*
C200.36799 (10)0.09339 (8)0.38122 (7)0.0229 (3)
H20A0.37500.08670.42610.034*
H20B0.41320.05180.36860.034*
H20C0.30250.08820.37340.034*
C210.37749 (10)0.18370 (9)0.27524 (6)0.0247 (3)
H21A0.42380.14240.26300.037*
H21B0.38930.23730.25010.037*
H21C0.31250.17700.26790.037*
C220.48842 (9)0.18242 (8)0.35574 (6)0.0206 (3)
H22A0.49680.17190.40100.031*
H22B0.50050.23700.33360.031*
H22C0.53350.14320.34040.031*
O10.13203 (7)0.14615 (7)0.36965 (5)0.0334 (2)
C230.05544 (11)0.12979 (9)0.36045 (7)0.0263 (3)
C240.03168 (13)0.14734 (13)0.39853 (9)0.0472 (5)
H24A0.01360.16400.43390.071*
H24B0.06150.09880.41450.071*
H24C0.07710.19080.37210.071*
C250.04366 (15)0.09457 (12)0.30869 (8)0.0465 (5)
H25A0.10640.08060.29010.070*
H25B0.00260.13400.27640.070*
H25C0.01420.04590.32550.070*
O20.90315 (8)0.81071 (7)0.13537 (6)0.0373 (3)
C260.97511 (10)0.83664 (9)0.11052 (7)0.0256 (3)
C271.06708 (11)0.78230 (10)0.10691 (8)0.0354 (4)
H27A1.11530.79270.13180.053*
H27B1.08900.79250.06300.053*
H27C1.05730.72600.12360.053*
C280.97528 (13)0.92445 (10)0.08092 (9)0.0392 (4)
H28A0.97900.93570.03510.059*
H28B1.03070.94030.09540.059*
H28C0.91630.95510.09280.059*
B10.73124 (10)0.50461 (8)0.35535 (6)0.0145 (3)
C290.63251 (9)0.56156 (7)0.32308 (6)0.0150 (2)
C300.58480 (9)0.55070 (8)0.27418 (6)0.0199 (3)
H300.60930.50650.25830.024*
C310.50251 (10)0.60210 (8)0.24754 (7)0.0249 (3)
H310.47210.59220.21440.030*
C320.46503 (9)0.66747 (8)0.26921 (7)0.0232 (3)
H320.40950.70310.25090.028*
C330.51005 (10)0.67986 (8)0.31820 (7)0.0222 (3)
H330.48510.72410.33390.027*
C340.59141 (9)0.62778 (8)0.34428 (6)0.0200 (3)
H340.62070.63730.37800.024*
C350.70822 (9)0.44652 (7)0.42565 (6)0.0154 (2)
C360.78258 (10)0.39271 (8)0.46173 (6)0.0200 (3)
H360.84510.38860.44360.024*
C370.76879 (10)0.34518 (8)0.52270 (6)0.0227 (3)
H370.82150.31050.54570.027*
C380.67795 (11)0.34853 (8)0.54986 (6)0.0237 (3)
H380.66800.31690.59170.028*
C390.60202 (10)0.39841 (8)0.51533 (6)0.0236 (3)
H390.53920.40010.53310.028*
C400.61746 (9)0.44649 (8)0.45430 (6)0.0192 (3)
H400.56430.48040.43140.023*
C410.78052 (9)0.44510 (7)0.31305 (5)0.0147 (2)
C420.73995 (9)0.37708 (7)0.31401 (6)0.0174 (2)
H420.68370.36740.33880.021*
C430.77838 (10)0.32334 (8)0.28041 (6)0.0197 (3)
H430.74790.27860.28220.024*
C440.86123 (10)0.33495 (8)0.24428 (6)0.0203 (3)
H440.88810.29830.22150.024*
C450.90389 (9)0.40097 (8)0.24213 (6)0.0196 (3)
H450.96070.40970.21780.023*
C460.86353 (9)0.45484 (8)0.27571 (6)0.0171 (2)
H460.89370.50000.27310.021*
C470.80014 (9)0.56870 (7)0.36063 (6)0.0152 (2)
C480.82057 (9)0.63030 (7)0.30710 (6)0.0186 (3)
H480.79870.63080.26750.022*
C490.87125 (10)0.69042 (8)0.30944 (7)0.0229 (3)
H490.88320.73080.27200.027*
C500.90441 (10)0.69138 (8)0.36650 (7)0.0254 (3)
H500.93890.73220.36870.030*
C510.88612 (10)0.63170 (8)0.42001 (7)0.0250 (3)
H510.90880.63120.45940.030*
C520.83471 (10)0.57201 (8)0.41695 (6)0.0198 (3)
H520.82280.53210.45470.024*
B20.25154 (10)0.48260 (8)0.14556 (6)0.0143 (3)
C530.35673 (9)0.43199 (7)0.17107 (6)0.0151 (2)
C540.39992 (9)0.43296 (7)0.22558 (6)0.0181 (2)
H540.36830.46720.24920.022*
C550.48748 (10)0.38577 (8)0.24654 (6)0.0216 (3)
H550.51420.38830.28380.026*
C560.53581 (9)0.33514 (8)0.21329 (7)0.0227 (3)
H560.59570.30320.22730.027*
C570.49517 (9)0.33187 (8)0.15917 (6)0.0210 (3)
H570.52700.29720.13600.025*
C580.40797 (9)0.37934 (7)0.13895 (6)0.0182 (3)
H580.38160.37620.10180.022*
C590.18616 (9)0.41291 (7)0.14802 (6)0.0163 (2)
C600.17790 (9)0.35183 (8)0.20447 (6)0.0201 (3)
H600.20590.35490.24110.024*
C610.13078 (10)0.28712 (8)0.20928 (7)0.0245 (3)
H610.12740.24730.24850.029*
C620.08871 (10)0.28067 (9)0.15679 (7)0.0271 (3)
H620.05750.23610.15940.032*
C630.09326 (11)0.34039 (10)0.10076 (7)0.0323 (3)
H630.06370.33760.06450.039*
C640.14105 (11)0.40498 (9)0.09687 (6)0.0263 (3)
H640.14290.44520.05770.032*
C650.25935 (9)0.54335 (7)0.07414 (6)0.0167 (2)
C660.17740 (10)0.59419 (8)0.04480 (6)0.0225 (3)
H660.11770.59110.06660.027*
C670.17972 (11)0.64881 (8)0.01465 (7)0.0270 (3)
H670.12230.68140.03280.032*
C680.26575 (12)0.65573 (8)0.04738 (6)0.0266 (3)
H680.26790.69280.08810.032*
C690.34830 (11)0.60797 (8)0.01988 (6)0.0257 (3)
H690.40790.61270.04160.031*
C700.34470 (10)0.55272 (8)0.03959 (6)0.0200 (3)
H700.40250.52020.05730.024*
C710.20511 (9)0.54107 (7)0.18889 (6)0.0149 (2)
C720.25152 (9)0.60399 (8)0.19299 (6)0.0183 (3)
H720.31120.61000.17170.022*
C730.21409 (10)0.65752 (8)0.22673 (6)0.0217 (3)
H730.24900.69800.22920.026*
C740.12553 (10)0.65194 (8)0.25693 (6)0.0224 (3)
H740.09920.68860.27990.027*
C750.07637 (9)0.59213 (8)0.25294 (6)0.0203 (3)
H750.01510.58830.27250.024*
C760.11633 (9)0.53736 (7)0.22030 (6)0.0168 (2)
H760.08200.49590.21930.020*
B30.25906 (10)0.99580 (8)0.12831 (6)0.0134 (3)
C770.27088 (9)0.93178 (7)0.08536 (6)0.0151 (2)
C780.31932 (9)0.85227 (8)0.10491 (6)0.0191 (3)
H780.34610.83290.14570.023*
C790.32999 (10)0.80033 (8)0.06712 (7)0.0250 (3)
H790.36310.74680.08260.030*
C800.29283 (10)0.82617 (9)0.00744 (7)0.0264 (3)
H800.29970.79090.01830.032*
C810.24530 (10)0.90448 (9)0.01421 (7)0.0259 (3)
H810.21970.92350.05530.031*
C820.23489 (10)0.95547 (8)0.02409 (6)0.0211 (3)
H820.20191.00890.00810.025*
C830.28744 (8)0.94719 (7)0.20161 (6)0.0143 (2)
C840.24970 (9)0.87692 (7)0.23391 (6)0.0167 (2)
H840.20530.85920.21300.020*
C850.27460 (9)0.83237 (8)0.29507 (6)0.0187 (3)
H850.24790.78490.31480.022*
C860.33842 (9)0.85702 (8)0.32745 (6)0.0202 (3)
H860.35600.82660.36920.024*
C870.37598 (10)0.92650 (8)0.29794 (6)0.0204 (3)
H870.41920.94440.31960.025*
C880.35058 (9)0.97033 (8)0.23640 (6)0.0171 (2)
H880.37721.01790.21720.020*
C890.14791 (9)1.04397 (7)0.12482 (6)0.0144 (2)
C900.11600 (9)1.10691 (8)0.07111 (6)0.0181 (2)
H900.16041.12180.03760.022*
C910.02294 (10)1.14836 (8)0.06457 (6)0.0207 (3)
H910.00511.19030.02720.025*
C920.04398 (9)1.12862 (8)0.11255 (6)0.0211 (3)
H920.10801.15620.10830.025*
C930.01551 (9)1.06792 (8)0.16684 (6)0.0206 (3)
H930.06021.05390.20030.025*
C940.07857 (9)1.02723 (8)0.17261 (6)0.0174 (2)
H940.09630.98640.21060.021*
C950.33082 (9)1.06264 (7)0.10002 (5)0.0144 (2)
C960.31729 (9)1.13486 (7)0.11712 (6)0.0180 (2)
H960.26331.14570.14270.022*
C970.37946 (10)1.19096 (8)0.09825 (6)0.0211 (3)
H970.36781.23870.11120.025*
C980.45864 (10)1.17713 (8)0.06044 (6)0.0215 (3)
H980.50151.21520.04740.026*
C990.47446 (9)1.10714 (8)0.04191 (6)0.0202 (3)
H990.52811.09710.01590.024*
C1000.41121 (9)1.05129 (7)0.06164 (6)0.0166 (2)
H1000.42331.00370.04850.020*
B40.73431 (10)0.99633 (8)0.37926 (6)0.0139 (3)
C1010.73191 (8)1.05294 (7)0.42675 (6)0.0144 (2)
C1020.71416 (9)1.13735 (7)0.40836 (6)0.0169 (2)
H1020.69781.16490.36590.020*
C1030.71942 (9)1.18296 (8)0.44961 (6)0.0203 (3)
H1030.70691.24020.43490.024*
C1040.74287 (9)1.14494 (8)0.51182 (6)0.0207 (3)
H1040.74851.17560.53980.025*
C1050.75813 (9)1.06126 (8)0.53281 (6)0.0199 (3)
H1050.77291.03420.57560.024*
C1060.75168 (9)1.01714 (8)0.49108 (6)0.0168 (2)
H1060.76110.96000.50670.020*
C1070.66263 (9)0.92926 (7)0.40695 (5)0.0146 (2)
C1080.67618 (9)0.85512 (7)0.39293 (6)0.0181 (2)
H1080.73270.84060.37080.022*
C1090.61016 (10)0.80235 (8)0.41024 (6)0.0219 (3)
H1090.62210.75300.39960.026*
C1100.52682 (10)0.82079 (8)0.44300 (6)0.0211 (3)
H1100.48170.78460.45480.025*
C1110.51070 (9)0.89320 (8)0.45813 (6)0.0186 (3)
H1110.45410.90700.48040.022*
C1120.57788 (9)0.94569 (7)0.44047 (6)0.0153 (2)
H1120.56570.99470.45160.018*
C1130.84502 (9)0.95046 (7)0.37163 (6)0.0171 (2)
C1140.87449 (10)0.92849 (8)0.31665 (6)0.0215 (3)
H1140.82990.94110.28370.026*
C1150.96626 (10)0.88903 (8)0.30825 (7)0.0284 (3)
H1150.98310.87580.27010.034*
C1161.03263 (11)0.86919 (9)0.35537 (8)0.0346 (4)
H1161.09530.84230.35000.042*
C1171.00659 (10)0.88896 (10)0.41035 (8)0.0341 (4)
H1171.05130.87510.44330.041*
C1180.91482 (10)0.92922 (9)0.41785 (7)0.0247 (3)
H1180.89910.94280.45600.030*
C1190.69929 (9)1.04997 (7)0.30787 (6)0.0146 (2)
C1200.75272 (9)1.10808 (7)0.27122 (6)0.0177 (2)
H1200.80591.11840.28970.021*
C1210.73128 (10)1.15105 (8)0.20929 (6)0.0211 (3)
H1210.76891.19030.18660.025*
C1220.65482 (10)1.13683 (8)0.18036 (6)0.0222 (3)
H1220.64071.16520.13770.027*
C1230.59957 (10)1.08066 (8)0.21476 (6)0.0208 (3)
H1230.54661.07070.19580.025*
C1240.62159 (9)1.03844 (7)0.27750 (6)0.0174 (2)
H1240.58241.00060.30030.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0251 (6)0.0208 (5)0.0171 (5)0.0025 (5)0.0011 (4)0.0064 (4)
N20.0278 (6)0.0184 (5)0.0221 (6)0.0080 (5)0.0022 (5)0.0064 (4)
N30.0231 (6)0.0154 (5)0.0182 (5)0.0052 (4)0.0002 (4)0.0034 (4)
N40.0225 (6)0.0168 (5)0.0207 (5)0.0019 (4)0.0002 (4)0.0055 (4)
C10.0246 (7)0.0168 (6)0.0114 (5)0.0041 (5)0.0013 (5)0.0035 (5)
C20.0215 (7)0.0324 (8)0.0271 (7)0.0030 (6)0.0024 (6)0.0081 (6)
C30.0408 (9)0.0237 (7)0.0206 (7)0.0041 (6)0.0017 (6)0.0090 (6)
C40.0474 (9)0.0179 (7)0.0242 (7)0.0136 (6)0.0063 (6)0.0076 (6)
C50.0302 (8)0.0336 (8)0.0373 (8)0.0108 (6)0.0075 (6)0.0138 (7)
C60.0287 (7)0.0217 (7)0.0187 (6)0.0098 (6)0.0006 (5)0.0015 (5)
C70.0188 (6)0.0185 (6)0.0273 (7)0.0018 (5)0.0027 (5)0.0071 (5)
C80.0209 (7)0.0142 (6)0.0231 (6)0.0022 (5)0.0035 (5)0.0050 (5)
C90.0274 (7)0.0183 (6)0.0303 (7)0.0052 (6)0.0009 (6)0.0023 (6)
C100.0591 (11)0.0331 (9)0.0331 (9)0.0091 (8)0.0145 (8)0.0211 (7)
C110.0235 (8)0.0273 (8)0.0407 (9)0.0039 (6)0.0098 (6)0.0019 (7)
N80.0138 (5)0.0164 (5)0.0157 (5)0.0012 (4)0.0005 (4)0.0025 (4)
C12A0.0209 (6)0.0232 (6)0.0127 (9)0.0042 (5)0.0032 (5)0.0091 (5)
N5A0.0298 (7)0.0191 (6)0.0191 (6)0.0016 (5)0.0070 (5)0.0065 (5)
N6A0.0227 (6)0.0269 (7)0.0199 (6)0.0082 (5)0.0025 (5)0.0081 (5)
N7A0.0174 (6)0.0205 (6)0.0217 (6)0.0030 (5)0.0037 (5)0.0100 (5)
C13A0.0317 (9)0.0231 (8)0.0243 (8)0.0031 (7)0.0118 (6)0.0085 (8)
C14A0.0419 (11)0.0206 (7)0.0211 (10)0.0025 (7)0.0050 (8)0.0050 (8)
C15A0.0366 (10)0.0297 (9)0.0265 (8)0.0157 (7)0.0019 (7)0.0091 (7)
C16A0.0205 (7)0.0447 (19)0.0267 (16)0.0012 (10)0.0069 (8)0.0082 (9)
C17A0.0261 (8)0.0235 (8)0.0229 (7)0.0033 (6)0.0024 (7)0.0089 (6)
C18A0.0181 (9)0.0184 (8)0.0237 (8)0.0042 (6)0.0052 (6)0.0091 (6)
C12B0.0209 (6)0.0232 (6)0.0127 (9)0.0042 (5)0.0032 (5)0.0091 (5)
N5B0.0298 (7)0.0191 (6)0.0191 (6)0.0016 (5)0.0070 (5)0.0065 (5)
N6B0.0227 (6)0.0269 (7)0.0199 (6)0.0082 (5)0.0025 (5)0.0081 (5)
N7B0.0174 (6)0.0205 (6)0.0217 (6)0.0030 (5)0.0037 (5)0.0100 (5)
C13B0.0261 (8)0.0235 (8)0.0229 (7)0.0033 (6)0.0024 (7)0.0089 (6)
C14B0.0205 (7)0.0447 (19)0.0267 (16)0.0012 (10)0.0069 (8)0.0082 (9)
C15B0.0366 (10)0.0297 (9)0.0265 (8)0.0157 (7)0.0019 (7)0.0091 (7)
C16B0.0419 (11)0.0206 (7)0.0211 (10)0.0025 (7)0.0050 (8)0.0050 (8)
C17B0.0317 (9)0.0231 (8)0.0243 (8)0.0031 (7)0.0118 (6)0.0085 (8)
C18B0.0181 (9)0.0184 (8)0.0237 (8)0.0042 (6)0.0052 (6)0.0091 (6)
C190.0161 (6)0.0173 (6)0.0196 (6)0.0033 (5)0.0019 (5)0.0038 (5)
C200.0249 (7)0.0153 (6)0.0266 (7)0.0037 (5)0.0021 (5)0.0023 (5)
C210.0231 (7)0.0341 (8)0.0164 (6)0.0017 (6)0.0002 (5)0.0080 (6)
C220.0133 (6)0.0244 (7)0.0235 (7)0.0025 (5)0.0002 (5)0.0061 (5)
O10.0240 (5)0.0442 (6)0.0384 (6)0.0120 (5)0.0031 (4)0.0174 (5)
C230.0293 (8)0.0269 (7)0.0239 (7)0.0132 (6)0.0046 (6)0.0031 (6)
C240.0319 (9)0.0654 (13)0.0527 (11)0.0209 (9)0.0061 (8)0.0240 (10)
C250.0659 (13)0.0535 (11)0.0334 (9)0.0408 (10)0.0058 (8)0.0164 (8)
O20.0245 (6)0.0459 (7)0.0441 (7)0.0139 (5)0.0031 (5)0.0129 (5)
C260.0210 (7)0.0336 (8)0.0246 (7)0.0077 (6)0.0054 (5)0.0090 (6)
C270.0239 (8)0.0430 (9)0.0333 (8)0.0017 (7)0.0047 (6)0.0028 (7)
C280.0417 (10)0.0335 (9)0.0477 (10)0.0122 (7)0.0101 (8)0.0142 (8)
B10.0152 (6)0.0135 (6)0.0148 (6)0.0010 (5)0.0009 (5)0.0044 (5)
C290.0159 (6)0.0134 (5)0.0146 (6)0.0035 (5)0.0020 (4)0.0023 (4)
C300.0202 (6)0.0181 (6)0.0226 (6)0.0017 (5)0.0023 (5)0.0080 (5)
C310.0223 (7)0.0244 (7)0.0287 (7)0.0031 (6)0.0096 (6)0.0072 (6)
C320.0143 (6)0.0188 (6)0.0319 (7)0.0007 (5)0.0037 (5)0.0008 (5)
C330.0203 (7)0.0169 (6)0.0280 (7)0.0008 (5)0.0019 (5)0.0068 (5)
C340.0214 (7)0.0187 (6)0.0196 (6)0.0001 (5)0.0014 (5)0.0067 (5)
C350.0190 (6)0.0127 (5)0.0157 (6)0.0027 (5)0.0004 (5)0.0059 (5)
C360.0204 (6)0.0175 (6)0.0209 (6)0.0024 (5)0.0002 (5)0.0044 (5)
C370.0299 (7)0.0153 (6)0.0211 (7)0.0019 (5)0.0067 (5)0.0020 (5)
C380.0368 (8)0.0176 (6)0.0160 (6)0.0086 (6)0.0014 (5)0.0017 (5)
C390.0264 (7)0.0221 (7)0.0219 (7)0.0070 (5)0.0061 (5)0.0051 (5)
C400.0200 (6)0.0171 (6)0.0194 (6)0.0019 (5)0.0008 (5)0.0042 (5)
C410.0155 (6)0.0141 (6)0.0130 (5)0.0009 (4)0.0036 (4)0.0026 (4)
C420.0180 (6)0.0149 (6)0.0174 (6)0.0017 (5)0.0005 (5)0.0024 (5)
C430.0241 (7)0.0139 (6)0.0210 (6)0.0032 (5)0.0024 (5)0.0043 (5)
C440.0236 (7)0.0175 (6)0.0199 (6)0.0023 (5)0.0019 (5)0.0086 (5)
C450.0173 (6)0.0228 (6)0.0185 (6)0.0011 (5)0.0015 (5)0.0073 (5)
C460.0166 (6)0.0172 (6)0.0184 (6)0.0034 (5)0.0007 (5)0.0060 (5)
C470.0131 (6)0.0139 (6)0.0184 (6)0.0012 (4)0.0012 (5)0.0063 (5)
C480.0183 (6)0.0164 (6)0.0201 (6)0.0010 (5)0.0005 (5)0.0047 (5)
C490.0209 (7)0.0142 (6)0.0300 (7)0.0018 (5)0.0047 (5)0.0026 (5)
C500.0230 (7)0.0172 (6)0.0396 (8)0.0057 (5)0.0020 (6)0.0129 (6)
C510.0285 (7)0.0239 (7)0.0276 (7)0.0058 (6)0.0011 (6)0.0140 (6)
C520.0234 (7)0.0184 (6)0.0186 (6)0.0038 (5)0.0013 (5)0.0070 (5)
B20.0143 (6)0.0142 (6)0.0147 (6)0.0031 (5)0.0001 (5)0.0042 (5)
C530.0155 (6)0.0123 (5)0.0165 (6)0.0051 (4)0.0024 (5)0.0015 (4)
C540.0192 (6)0.0159 (6)0.0194 (6)0.0040 (5)0.0001 (5)0.0048 (5)
C550.0207 (7)0.0191 (6)0.0240 (7)0.0053 (5)0.0056 (5)0.0021 (5)
C560.0151 (6)0.0160 (6)0.0321 (7)0.0027 (5)0.0007 (5)0.0009 (5)
C570.0204 (7)0.0142 (6)0.0261 (7)0.0029 (5)0.0069 (5)0.0037 (5)
C580.0205 (6)0.0155 (6)0.0185 (6)0.0043 (5)0.0017 (5)0.0046 (5)
C590.0140 (6)0.0169 (6)0.0191 (6)0.0026 (5)0.0018 (5)0.0072 (5)
C600.0182 (6)0.0178 (6)0.0234 (7)0.0043 (5)0.0036 (5)0.0029 (5)
C610.0212 (7)0.0163 (6)0.0332 (8)0.0041 (5)0.0022 (6)0.0026 (5)
C620.0233 (7)0.0249 (7)0.0408 (8)0.0115 (6)0.0090 (6)0.0191 (6)
C630.0369 (9)0.0450 (9)0.0275 (8)0.0220 (7)0.0051 (6)0.0219 (7)
C640.0326 (8)0.0331 (8)0.0179 (6)0.0155 (6)0.0029 (6)0.0095 (6)
C650.0223 (6)0.0135 (6)0.0157 (6)0.0039 (5)0.0010 (5)0.0058 (5)
C660.0250 (7)0.0205 (6)0.0207 (6)0.0008 (5)0.0018 (5)0.0060 (5)
C670.0387 (8)0.0175 (6)0.0226 (7)0.0039 (6)0.0098 (6)0.0052 (5)
C680.0506 (9)0.0152 (6)0.0144 (6)0.0079 (6)0.0022 (6)0.0030 (5)
C690.0366 (8)0.0223 (7)0.0191 (7)0.0123 (6)0.0054 (6)0.0046 (5)
C700.0233 (7)0.0181 (6)0.0185 (6)0.0060 (5)0.0006 (5)0.0036 (5)
C710.0152 (6)0.0143 (6)0.0139 (6)0.0010 (5)0.0028 (4)0.0019 (4)
C720.0145 (6)0.0176 (6)0.0228 (6)0.0027 (5)0.0018 (5)0.0055 (5)
C730.0204 (7)0.0174 (6)0.0293 (7)0.0025 (5)0.0062 (5)0.0091 (5)
C740.0234 (7)0.0207 (6)0.0246 (7)0.0014 (5)0.0030 (5)0.0114 (5)
C750.0159 (6)0.0235 (6)0.0209 (6)0.0004 (5)0.0010 (5)0.0073 (5)
C760.0160 (6)0.0169 (6)0.0181 (6)0.0035 (5)0.0020 (5)0.0052 (5)
B30.0139 (6)0.0124 (6)0.0139 (6)0.0022 (5)0.0003 (5)0.0039 (5)
C770.0131 (6)0.0164 (6)0.0174 (6)0.0063 (5)0.0028 (4)0.0058 (5)
C780.0197 (6)0.0176 (6)0.0212 (6)0.0064 (5)0.0042 (5)0.0063 (5)
C790.0268 (7)0.0174 (6)0.0333 (8)0.0077 (5)0.0113 (6)0.0111 (6)
C800.0273 (7)0.0303 (7)0.0326 (8)0.0160 (6)0.0124 (6)0.0221 (6)
C810.0261 (7)0.0360 (8)0.0222 (7)0.0106 (6)0.0012 (5)0.0156 (6)
C820.0218 (7)0.0222 (6)0.0210 (6)0.0042 (5)0.0009 (5)0.0086 (5)
C830.0130 (6)0.0136 (5)0.0154 (6)0.0006 (4)0.0012 (4)0.0047 (5)
C840.0141 (6)0.0174 (6)0.0175 (6)0.0015 (5)0.0004 (5)0.0040 (5)
C850.0177 (6)0.0164 (6)0.0183 (6)0.0006 (5)0.0037 (5)0.0019 (5)
C860.0207 (6)0.0226 (6)0.0139 (6)0.0054 (5)0.0008 (5)0.0047 (5)
C870.0216 (7)0.0232 (7)0.0181 (6)0.0000 (5)0.0040 (5)0.0097 (5)
C880.0178 (6)0.0167 (6)0.0175 (6)0.0019 (5)0.0009 (5)0.0067 (5)
C890.0162 (6)0.0137 (5)0.0157 (6)0.0034 (5)0.0010 (4)0.0069 (5)
C900.0197 (6)0.0189 (6)0.0161 (6)0.0045 (5)0.0002 (5)0.0051 (5)
C910.0228 (7)0.0193 (6)0.0188 (6)0.0000 (5)0.0052 (5)0.0044 (5)
C920.0154 (6)0.0236 (7)0.0257 (7)0.0017 (5)0.0040 (5)0.0112 (5)
C930.0174 (6)0.0247 (7)0.0203 (6)0.0036 (5)0.0024 (5)0.0081 (5)
C940.0179 (6)0.0181 (6)0.0162 (6)0.0027 (5)0.0006 (5)0.0049 (5)
C950.0164 (6)0.0132 (5)0.0132 (5)0.0026 (5)0.0032 (4)0.0026 (4)
C960.0200 (6)0.0163 (6)0.0185 (6)0.0031 (5)0.0014 (5)0.0057 (5)
C970.0262 (7)0.0141 (6)0.0244 (7)0.0059 (5)0.0076 (5)0.0047 (5)
C980.0224 (7)0.0199 (6)0.0211 (6)0.0109 (5)0.0055 (5)0.0012 (5)
C990.0169 (6)0.0248 (7)0.0177 (6)0.0065 (5)0.0001 (5)0.0027 (5)
C1000.0180 (6)0.0164 (6)0.0155 (6)0.0038 (5)0.0015 (5)0.0037 (5)
B40.0149 (6)0.0133 (6)0.0128 (6)0.0023 (5)0.0005 (5)0.0025 (5)
C1010.0114 (6)0.0159 (6)0.0165 (6)0.0044 (4)0.0012 (4)0.0047 (5)
C1020.0165 (6)0.0178 (6)0.0164 (6)0.0047 (5)0.0002 (5)0.0037 (5)
C1030.0224 (7)0.0152 (6)0.0248 (7)0.0068 (5)0.0029 (5)0.0065 (5)
C1040.0218 (7)0.0241 (7)0.0212 (6)0.0097 (5)0.0026 (5)0.0112 (5)
C1050.0212 (7)0.0244 (7)0.0153 (6)0.0092 (5)0.0007 (5)0.0047 (5)
C1060.0166 (6)0.0166 (6)0.0170 (6)0.0058 (5)0.0008 (5)0.0030 (5)
C1070.0163 (6)0.0143 (6)0.0121 (5)0.0024 (5)0.0037 (4)0.0015 (4)
C1080.0221 (7)0.0163 (6)0.0161 (6)0.0030 (5)0.0015 (5)0.0048 (5)
C1090.0321 (7)0.0146 (6)0.0202 (6)0.0062 (5)0.0063 (5)0.0043 (5)
C1100.0238 (7)0.0199 (6)0.0193 (6)0.0113 (5)0.0072 (5)0.0008 (5)
C1110.0156 (6)0.0207 (6)0.0167 (6)0.0049 (5)0.0030 (5)0.0005 (5)
C1120.0159 (6)0.0137 (6)0.0157 (6)0.0026 (5)0.0030 (4)0.0024 (5)
C1130.0160 (6)0.0132 (6)0.0192 (6)0.0035 (5)0.0024 (5)0.0002 (5)
C1140.0224 (7)0.0162 (6)0.0241 (7)0.0038 (5)0.0053 (5)0.0038 (5)
C1150.0271 (8)0.0197 (7)0.0339 (8)0.0027 (6)0.0143 (6)0.0044 (6)
C1160.0171 (7)0.0272 (8)0.0485 (10)0.0018 (6)0.0117 (7)0.0004 (7)
C1170.0160 (7)0.0384 (9)0.0387 (9)0.0007 (6)0.0028 (6)0.0013 (7)
C1180.0178 (7)0.0282 (7)0.0239 (7)0.0031 (5)0.0002 (5)0.0012 (6)
C1190.0163 (6)0.0129 (5)0.0144 (6)0.0008 (4)0.0012 (4)0.0057 (4)
C1200.0180 (6)0.0158 (6)0.0183 (6)0.0011 (5)0.0015 (5)0.0045 (5)
C1210.0253 (7)0.0160 (6)0.0180 (6)0.0002 (5)0.0050 (5)0.0019 (5)
C1220.0288 (7)0.0202 (6)0.0128 (6)0.0069 (5)0.0017 (5)0.0034 (5)
C1230.0228 (7)0.0214 (6)0.0188 (6)0.0037 (5)0.0049 (5)0.0096 (5)
C1240.0191 (6)0.0163 (6)0.0172 (6)0.0007 (5)0.0006 (5)0.0069 (5)
Geometric parameters (Å, º) top
N1—C11.3329 (17)C44—C451.3858 (18)
N1—C21.4654 (18)C44—H440.9500
N1—C31.4698 (17)C45—C461.3991 (17)
N2—C11.3371 (17)C45—H450.9500
N2—C51.4626 (19)C46—H460.9500
N2—C41.4677 (17)C47—C521.3957 (18)
N3—C11.3548 (16)C47—C481.4072 (17)
N3—C61.4611 (16)C48—C491.3911 (18)
N3—C71.4639 (17)C48—H480.9500
N4—C111.4903 (18)C49—C501.388 (2)
N4—C91.4983 (17)C49—H490.9500
N4—C101.5052 (19)C50—C511.380 (2)
N4—C81.5114 (16)C50—H500.9500
C2—H2A0.9800C51—C521.3960 (18)
C2—H2B0.9800C51—H510.9500
C2—H2C0.9800C52—H520.9500
C3—H3A0.9800B2—C711.6394 (18)
C3—H3B0.9800B2—C531.6431 (18)
C3—H3C0.9800B2—C651.6430 (18)
C4—H4A0.9800B2—C591.6457 (18)
C4—H4B0.9800C53—C541.4003 (17)
C4—H4C0.9800C53—C581.4092 (17)
C5—H5A0.9800C54—C551.3945 (18)
C5—H5B0.9800C54—H540.9500
C5—H5C0.9800C55—C561.386 (2)
C6—H6A0.9800C55—H550.9500
C6—H6B0.9800C56—C571.389 (2)
C6—H6C0.9800C56—H560.9500
C7—C81.5376 (18)C57—C581.3883 (18)
C7—H7A0.9900C57—H570.9500
C7—H7B0.9900C58—H580.9500
C8—H8A0.9900C59—C641.3944 (18)
C8—H8B0.9900C59—C601.4058 (18)
C9—H9A0.9800C60—C611.3901 (18)
C9—H9B0.9800C60—H600.9500
C9—H9C0.9800C61—C621.388 (2)
C10—H10A0.9800C61—H610.9500
C10—H10B0.9800C62—C631.380 (2)
C10—H10C0.9800C62—H620.9500
C11—H11A0.9800C63—C641.398 (2)
C11—H11B0.9800C63—H630.9500
C11—H11C0.9800C64—H640.9500
N8—C221.4969 (16)C65—C701.3988 (18)
N8—C201.4980 (16)C65—C661.4060 (18)
N8—C211.5043 (16)C66—C671.3901 (19)
N8—C191.5060 (16)C66—H660.9500
C12A—N5A1.335 (2)C67—C681.385 (2)
C12A—N6A1.342 (2)C67—H670.9500
C12A—N7A1.352 (2)C68—C691.381 (2)
N5A—C13A1.4623 (19)C68—H680.9500
N5A—C14A1.471 (2)C69—C701.3966 (18)
N6A—C16A1.466 (4)C69—H690.9500
N6A—C15A1.4657 (19)C70—H700.9500
N7A—C18A1.460 (2)C71—C761.4020 (17)
N7A—C17A1.4818 (19)C71—C721.4079 (17)
C13A—H13A0.9800C72—C731.3868 (18)
C13A—H13B0.9800C72—H720.9500
C13A—H13C0.9800C73—C741.3903 (19)
C14A—H14A0.9800C73—H730.9500
C14A—H14B0.9800C74—C751.3839 (19)
C14A—H14C0.9800C74—H740.9500
C15A—H15A0.9800C75—C761.3949 (18)
C15A—H15B0.9800C75—H750.9500
C15A—H15C0.9800C76—H760.9500
C16A—H16A0.9800B3—C831.6439 (18)
C16A—H16B0.9800B3—C951.6448 (18)
C16A—H16C0.9800B3—C891.6521 (18)
C17A—H17A0.9800B3—C771.6598 (18)
C17A—H17B0.9800C77—C781.4028 (18)
C17A—H17C0.9800C77—C821.4064 (18)
C18A—C191.530 (2)C78—C791.3969 (18)
C18A—H18A0.9900C78—H780.9500
C18A—H18B0.9900C79—C801.380 (2)
C12B—N5B1.341 (18)C79—H790.9500
C12B—N6B1.349 (16)C80—C811.384 (2)
C12B—N7B1.364 (16)C80—H800.9500
N5B—C14B1.469 (18)C81—C821.3925 (18)
N5B—C13B1.488 (16)C81—H810.9500
N6B—C15B1.457 (16)C82—H820.9500
N6B—C16B1.482 (18)C83—C881.4030 (17)
N7B—C18B1.476 (16)C83—C841.4085 (17)
N7B—C17B1.488 (16)C84—C851.3900 (17)
C13B—H13D0.9800C84—H840.9500
C13B—H13E0.9800C85—C861.3894 (19)
C13B—H13F0.9800C85—H850.9500
C14B—H14D0.9800C86—C871.3832 (19)
C14B—H14E0.9800C86—H860.9500
C14B—H14F0.9800C87—C881.3959 (18)
C15B—H15D0.9800C87—H870.9500
C15B—H15E0.9800C88—H880.9500
C15B—H15F0.9800C89—C941.4014 (17)
C16B—H16D0.9800C89—C901.4071 (17)
C16B—H16E0.9800C90—C911.3886 (18)
C16B—H16F0.9800C90—H900.9500
C17B—H17D0.9800C91—C921.3872 (19)
C17B—H17E0.9800C91—H910.9500
C17B—H17F0.9800C92—C931.3857 (19)
C18B—C191.542 (10)C92—H920.9500
C18B—H18C0.9900C93—C941.3967 (18)
C18B—H18D0.9900C93—H930.9500
C19—H19A0.9900C94—H940.9500
C19—H19B0.9900C95—C1001.4018 (17)
C20—H20A0.9800C95—C961.4086 (17)
C20—H20B0.9800C96—C971.3907 (18)
C20—H20C0.9800C96—H960.9500
C21—H21A0.9800C97—C981.390 (2)
C21—H21B0.9800C97—H970.9500
C21—H21C0.9800C98—C991.3878 (19)
C22—H22A0.9800C98—H980.9500
C22—H22B0.9800C99—C1001.3997 (17)
C22—H22C0.9800C99—H990.9500
O1—C231.2152 (17)C100—H1000.9500
C23—C251.489 (2)B4—C1071.6451 (18)
C23—C241.492 (2)B4—C1011.6464 (18)
C24—H24A0.9800B4—C1191.6501 (17)
C24—H24B0.9800B4—C1131.6607 (18)
C24—H24C0.9800C101—C1021.4005 (17)
C25—H25A0.9800C101—C1061.4094 (17)
C25—H25B0.9800C102—C1031.3976 (18)
C25—H25C0.9800C102—H1020.9500
O2—C261.2221 (17)C103—C1041.3836 (19)
C26—C281.490 (2)C103—H1030.9500
C26—C271.492 (2)C104—C1051.3890 (19)
C27—H27A0.9800C104—H1040.9500
C27—H27B0.9800C105—C1061.3897 (18)
C27—H27C0.9800C105—H1050.9500
C28—H28A0.9800C106—H1060.9500
C28—H28B0.9800C107—C1121.4056 (17)
C28—H28C0.9800C107—C1081.4066 (17)
B1—C351.6449 (18)C108—C1091.3883 (18)
B1—C291.6457 (18)C108—H1080.9500
B1—C471.6463 (18)C109—C1101.389 (2)
B1—C411.6465 (18)C109—H1090.9500
C29—C301.3934 (18)C110—C1111.3885 (19)
C29—C341.4042 (17)C110—H1100.9500
C30—C311.3947 (19)C111—C1121.3979 (17)
C30—H300.9500C111—H1110.9500
C31—C321.385 (2)C112—H1120.9500
C31—H310.9500C113—C1181.3998 (19)
C32—C331.387 (2)C113—C1141.4058 (18)
C32—H320.9500C114—C1151.3949 (19)
C33—C341.3859 (18)C114—H1140.9500
C33—H330.9500C115—C1161.382 (2)
C34—H340.9500C115—H1150.9500
C35—C401.3991 (17)C116—C1171.379 (2)
C35—C361.4054 (18)C116—H1160.9500
C36—C371.3901 (18)C117—C1181.396 (2)
C36—H360.9500C117—H1170.9500
C37—C381.387 (2)C118—H1180.9500
C37—H370.9500C119—C1241.4028 (17)
C38—C391.381 (2)C119—C1201.4066 (17)
C38—H380.9500C120—C1211.3882 (18)
C39—C401.3990 (18)C120—H1200.9500
C39—H390.9500C121—C1221.390 (2)
C40—H400.9500C121—H1210.9500
C41—C461.4014 (17)C122—C1231.385 (2)
C41—C421.4076 (17)C122—H1220.9500
C42—C431.3908 (18)C123—C1241.4022 (18)
C42—H420.9500C123—H1230.9500
C43—C441.3899 (19)C124—H1240.9500
C43—H430.9500
C1—N1—C2122.38 (11)C39—C40—C35122.55 (12)
C1—N1—C3122.06 (12)C39—C40—H40118.7
C2—N1—C3115.53 (12)C35—C40—H40118.7
C1—N2—C5122.18 (11)C46—C41—C42114.98 (11)
C1—N2—C4122.27 (12)C46—C41—B1125.29 (11)
C5—N2—C4115.44 (12)C42—C41—B1119.71 (11)
C1—N3—C6121.06 (11)C43—C42—C41123.03 (12)
C1—N3—C7122.72 (11)C43—C42—H42118.5
C6—N3—C7116.21 (10)C41—C42—H42118.5
C11—N4—C9109.37 (11)C44—C43—C42120.11 (12)
C11—N4—C10109.31 (12)C44—C43—H43119.9
C9—N4—C10108.30 (12)C42—C43—H43119.9
C11—N4—C8111.44 (11)C45—C44—C43118.86 (12)
C9—N4—C8111.66 (10)C45—C44—H44120.6
C10—N4—C8106.65 (10)C43—C44—H44120.6
N1—C1—N2120.76 (12)C44—C45—C46120.16 (12)
N1—C1—N3119.84 (12)C44—C45—H45119.9
N2—C1—N3119.40 (12)C46—C45—H45119.9
N1—C2—H2A109.5C45—C46—C41122.85 (12)
N1—C2—H2B109.5C45—C46—H46118.6
H2A—C2—H2B109.5C41—C46—H46118.6
N1—C2—H2C109.5C52—C47—C48115.01 (11)
H2A—C2—H2C109.5C52—C47—B1124.40 (11)
H2B—C2—H2C109.5C48—C47—B1120.32 (11)
N1—C3—H3A109.5C49—C48—C47123.07 (12)
N1—C3—H3B109.5C49—C48—H48118.5
H3A—C3—H3B109.5C47—C48—H48118.5
N1—C3—H3C109.5C50—C49—C48120.01 (12)
H3A—C3—H3C109.5C50—C49—H49120.0
H3B—C3—H3C109.5C48—C49—H49120.0
N2—C4—H4A109.5C51—C50—C49118.56 (12)
N2—C4—H4B109.5C51—C50—H50120.7
H4A—C4—H4B109.5C49—C50—H50120.7
N2—C4—H4C109.5C50—C51—C52120.76 (13)
H4A—C4—H4C109.5C50—C51—H51119.6
H4B—C4—H4C109.5C52—C51—H51119.6
N2—C5—H5A109.5C47—C52—C51122.58 (12)
N2—C5—H5B109.5C47—C52—H52118.7
H5A—C5—H5B109.5C51—C52—H52118.7
N2—C5—H5C109.5C71—B2—C53111.74 (10)
H5A—C5—H5C109.5C71—B2—C65105.30 (10)
H5B—C5—H5C109.5C53—B2—C65111.48 (10)
N3—C6—H6A109.5C71—B2—C59112.03 (10)
N3—C6—H6B109.5C53—B2—C59104.64 (10)
H6A—C6—H6B109.5C65—B2—C59111.82 (10)
N3—C6—H6C109.5C54—C53—C58115.10 (11)
H6A—C6—H6C109.5C54—C53—B2125.19 (11)
H6B—C6—H6C109.5C58—C53—B2119.63 (11)
N3—C7—C8110.22 (11)C55—C54—C53122.65 (12)
N3—C7—H7A109.6C55—C54—H54118.7
C8—C7—H7A109.6C53—C54—H54118.7
N3—C7—H7B109.6C56—C55—C54120.36 (13)
C8—C7—H7B109.6C56—C55—H55119.8
H7A—C7—H7B108.1C54—C55—H55119.8
N4—C8—C7115.88 (10)C55—C56—C57118.88 (12)
N4—C8—H8A108.3C55—C56—H56120.6
C7—C8—H8A108.3C57—C56—H56120.6
N4—C8—H8B108.3C58—C57—C56119.98 (12)
C7—C8—H8B108.3C58—C57—H57120.0
H8A—C8—H8B107.4C56—C57—H57120.0
N4—C9—H9A109.5C57—C58—C53123.03 (12)
N4—C9—H9B109.5C57—C58—H58118.5
H9A—C9—H9B109.5C53—C58—H58118.5
N4—C9—H9C109.5C64—C59—C60114.76 (12)
H9A—C9—H9C109.5C64—C59—B2125.53 (11)
H9B—C9—H9C109.5C60—C59—B2119.58 (11)
N4—C10—H10A109.5C61—C60—C59123.23 (13)
N4—C10—H10B109.5C61—C60—H60118.4
H10A—C10—H10B109.5C59—C60—H60118.4
N4—C10—H10C109.5C62—C61—C60120.06 (13)
H10A—C10—H10C109.5C62—C61—H61120.0
H10B—C10—H10C109.5C60—C61—H61120.0
N4—C11—H11A109.5C63—C62—C61118.54 (12)
N4—C11—H11B109.5C63—C62—H62120.7
H11A—C11—H11B109.5C61—C62—H62120.7
N4—C11—H11C109.5C62—C63—C64120.53 (14)
H11A—C11—H11C109.5C62—C63—H63119.7
H11B—C11—H11C109.5C64—C63—H63119.7
C22—N8—C20109.21 (10)C59—C64—C63122.85 (13)
C22—N8—C21109.69 (10)C59—C64—H64118.6
C20—N8—C21108.45 (10)C63—C64—H64118.6
C22—N8—C19111.56 (10)C70—C65—C66115.06 (12)
C20—N8—C19110.53 (10)C70—C65—B2124.66 (11)
C21—N8—C19107.34 (10)C66—C65—B2120.18 (11)
N5A—C12A—N6A120.29 (15)C67—C66—C65123.01 (13)
N5A—C12A—N7A120.41 (15)C67—C66—H66118.5
N6A—C12A—N7A119.28 (17)C65—C66—H66118.5
C12A—N5A—C13A122.70 (15)C68—C67—C66119.99 (13)
C12A—N5A—C14A122.35 (15)C68—C67—H67120.0
C13A—N5A—C14A114.87 (13)C66—C67—H67120.0
C12A—N6A—C16A122.3 (3)C69—C68—C67118.95 (12)
C12A—N6A—C15A122.18 (17)C69—C68—H68120.5
C16A—N6A—C15A115.5 (3)C67—C68—H68120.5
C12A—N7A—C18A121.87 (15)C68—C69—C70120.41 (13)
C12A—N7A—C17A122.73 (15)C68—C69—H69119.8
C18A—N7A—C17A114.90 (12)C70—C69—H69119.8
N5A—C13A—H13A109.5C69—C70—C65122.56 (13)
N5A—C13A—H13B109.5C69—C70—H70118.7
H13A—C13A—H13B109.5C65—C70—H70118.7
N5A—C13A—H13C109.5C76—C71—C72115.06 (11)
H13A—C13A—H13C109.5C76—C71—B2124.59 (11)
H13B—C13A—H13C109.5C72—C71—B2120.20 (11)
N5A—C14A—H14A109.5C73—C72—C71123.01 (12)
N5A—C14A—H14B109.5C73—C72—H72118.5
H14A—C14A—H14B109.5C71—C72—H72118.5
N5A—C14A—H14C109.5C72—C73—C74120.02 (12)
H14A—C14A—H14C109.5C72—C73—H73120.0
H14B—C14A—H14C109.5C74—C73—H73120.0
N6A—C15A—H15A109.5C75—C74—C73118.90 (12)
N6A—C15A—H15B109.5C75—C74—H74120.6
H15A—C15A—H15B109.5C73—C74—H74120.6
N6A—C15A—H15C109.5C74—C75—C76120.30 (12)
H15A—C15A—H15C109.5C74—C75—H75119.9
H15B—C15A—H15C109.5C76—C75—H75119.9
N6A—C16A—H16A109.5C75—C76—C71122.66 (12)
N6A—C16A—H16B109.5C75—C76—H76118.7
H16A—C16A—H16B109.5C71—C76—H76118.7
N6A—C16A—H16C109.5C83—B3—C95108.90 (10)
H16A—C16A—H16C109.5C83—B3—C89110.27 (10)
H16B—C16A—H16C109.5C95—B3—C89108.35 (9)
N7A—C17A—H17A109.5C83—B3—C77110.13 (10)
N7A—C17A—H17B109.5C95—B3—C77109.37 (9)
H17A—C17A—H17B109.5C89—B3—C77109.79 (10)
N7A—C17A—H17C109.5C78—C77—C82114.48 (11)
H17A—C17A—H17C109.5C78—C77—B3124.24 (11)
H17B—C17A—H17C109.5C82—C77—B3121.23 (11)
N7A—C18A—C19107.99 (12)C79—C78—C77122.95 (13)
N7A—C18A—H18A110.1C79—C78—H78118.5
C19—C18A—H18A110.1C77—C78—H78118.5
N7A—C18A—H18B110.1C80—C79—C78120.45 (13)
C19—C18A—H18B110.1C80—C79—H79119.8
H18A—C18A—H18B108.4C78—C79—H79119.8
N5B—C12B—N6B117.4 (17)C79—C80—C81118.71 (12)
N5B—C12B—N7B120.1 (17)C79—C80—H80120.6
N6B—C12B—N7B119.9 (17)C81—C80—H80120.6
C12B—N5B—C14B122 (2)C80—C81—C82120.19 (13)
C12B—N5B—C13B124 (2)C80—C81—H81119.9
C14B—N5B—C13B113 (2)C82—C81—H81119.9
C12B—N6B—C15B125 (2)C81—C82—C77123.21 (13)
C12B—N6B—C16B122 (2)C81—C82—H82118.4
C15B—N6B—C16B110.5 (19)C77—C82—H82118.4
C12B—N7B—C18B120.3 (19)C88—C83—C84114.93 (11)
C12B—N7B—C17B120.9 (19)C88—C83—B3123.99 (11)
C18B—N7B—C17B118.8 (15)C84—C83—B3121.07 (11)
N5B—C13B—H13D109.5C85—C84—C83122.89 (12)
N5B—C13B—H13E109.5C85—C84—H84118.6
H13D—C13B—H13E109.5C83—C84—H84118.6
N5B—C13B—H13F109.5C86—C85—C84120.18 (12)
H13D—C13B—H13F109.5C86—C85—H85119.9
H13E—C13B—H13F109.5C84—C85—H85119.9
N5B—C14B—H14D109.5C87—C86—C85118.91 (12)
N5B—C14B—H14E109.5C87—C86—H86120.5
H14D—C14B—H14E109.5C85—C86—H86120.5
N5B—C14B—H14F109.5C86—C87—C88120.19 (12)
H14D—C14B—H14F109.5C86—C87—H87119.9
H14E—C14B—H14F109.5C88—C87—H87119.9
N6B—C15B—H15D109.5C87—C88—C83122.89 (12)
N6B—C15B—H15E109.5C87—C88—H88118.6
H15D—C15B—H15E109.5C83—C88—H88118.6
N6B—C15B—H15F109.5C94—C89—C90114.58 (11)
H15D—C15B—H15F109.5C94—C89—B3124.85 (11)
H15E—C15B—H15F109.5C90—C89—B3120.56 (11)
N6B—C16B—H16D109.5C91—C90—C89123.40 (12)
N6B—C16B—H16E109.5C91—C90—H90118.3
H16D—C16B—H16E109.5C89—C90—H90118.3
N6B—C16B—H16F109.5C92—C91—C90120.08 (12)
H16D—C16B—H16F109.5C92—C91—H91120.0
H16E—C16B—H16F109.5C90—C91—H91120.0
N7B—C17B—H17D109.5C93—C92—C91118.65 (12)
N7B—C17B—H17E109.4C93—C92—H92120.7
H17D—C17B—H17E109.5C91—C92—H92120.7
N7B—C17B—H17F109.5C92—C93—C94120.37 (12)
H17D—C17B—H17F109.5C92—C93—H93119.8
H17E—C17B—H17F109.5C94—C93—H93119.8
N7B—C18B—C19128.8 (17)C93—C94—C89122.89 (12)
N7B—C18B—H18C105.1C93—C94—H94118.6
C19—C18B—H18C105.2C89—C94—H94118.6
N7B—C18B—H18D105.0C100—C95—C96115.32 (11)
C19—C18B—H18D105.0C100—C95—B3124.25 (11)
H18C—C18B—H18D105.9C96—C95—B3120.32 (11)
N8—C19—C18A114.69 (11)C97—C96—C95122.88 (12)
N8—C19—C18B114.2 (10)C97—C96—H96118.6
N8—C19—H19A108.6C95—C96—H96118.6
C18A—C19—H19A108.6C98—C97—C96119.93 (12)
N8—C19—H19B108.6C98—C97—H97120.0
C18A—C19—H19B108.6C96—C97—H97120.0
H19A—C19—H19B107.6C99—C98—C97119.26 (12)
N8—C20—H20A109.5C99—C98—H98120.4
N8—C20—H20B109.5C97—C98—H98120.4
H20A—C20—H20B109.5C98—C99—C100119.89 (12)
N8—C20—H20C109.5C98—C99—H99120.1
H20A—C20—H20C109.5C100—C99—H99120.1
H20B—C20—H20C109.5C99—C100—C95122.71 (12)
N8—C21—H21A109.5C99—C100—H100118.6
N8—C21—H21B109.5C95—C100—H100118.6
H21A—C21—H21B109.5C107—B4—C101109.69 (9)
N8—C21—H21C109.5C107—B4—C119108.08 (10)
H21A—C21—H21C109.5C101—B4—C119111.98 (10)
H21B—C21—H21C109.5C107—B4—C113110.14 (10)
N8—C22—H22A109.5C101—B4—C113110.41 (10)
N8—C22—H22B109.5C119—B4—C113106.46 (9)
H22A—C22—H22B109.5C102—C101—C106114.65 (11)
N8—C22—H22C109.5C102—C101—B4125.10 (11)
H22A—C22—H22C109.5C106—C101—B4120.21 (11)
H22B—C22—H22C109.5C103—C102—C101123.01 (12)
O1—C23—C25121.22 (15)C103—C102—H102118.5
O1—C23—C24121.62 (14)C101—C102—H102118.5
C25—C23—C24117.11 (14)C104—C103—C102120.09 (12)
C23—C24—H24A109.5C104—C103—H103120.0
C23—C24—H24B109.5C102—C103—H103120.0
H24A—C24—H24B109.5C103—C104—C105119.04 (12)
C23—C24—H24C109.5C103—C104—H104120.5
H24A—C24—H24C109.5C105—C104—H104120.5
H24B—C24—H24C109.5C104—C105—C106119.85 (12)
C23—C25—H25A109.5C104—C105—H105120.1
C23—C25—H25B109.5C106—C105—H105120.1
H25A—C25—H25B109.5C105—C106—C101123.27 (12)
C23—C25—H25C109.5C105—C106—H106118.4
H25A—C25—H25C109.5C101—C106—H106118.4
H25B—C25—H25C109.5C112—C107—C108115.15 (11)
O2—C26—C28121.72 (15)C112—C107—B4122.14 (11)
O2—C26—C27122.07 (14)C108—C107—B4122.36 (11)
C28—C26—C27116.19 (13)C109—C108—C107122.50 (12)
C26—C27—H27A109.5C109—C108—H108118.7
C26—C27—H27B109.5C107—C108—H108118.7
H27A—C27—H27B109.5C108—C109—C110120.80 (12)
C26—C27—H27C109.5C108—C109—H109119.6
H27A—C27—H27C109.5C110—C109—H109119.6
H27B—C27—H27C109.5C111—C110—C109118.67 (12)
C26—C28—H28A109.5C111—C110—H110120.7
C26—C28—H28B109.5C109—C110—H110120.7
H28A—C28—H28B109.5C110—C111—C112119.90 (12)
C26—C28—H28C109.5C110—C111—H111120.0
H28A—C28—H28C109.5C112—C111—H111120.0
H28B—C28—H28C109.5C111—C112—C107122.97 (12)
C35—B1—C29110.58 (10)C111—C112—H112118.5
C35—B1—C47110.31 (10)C107—C112—H112118.5
C29—B1—C47104.72 (9)C118—C113—C114114.84 (12)
C35—B1—C41107.25 (9)C118—C113—B4124.42 (11)
C29—B1—C41111.25 (10)C114—C113—B4120.73 (11)
C47—B1—C41112.77 (10)C115—C114—C113122.93 (14)
C30—C29—C34115.26 (11)C115—C114—H114118.5
C30—C29—B1125.14 (11)C113—C114—H114118.5
C34—C29—B1119.59 (11)C116—C115—C114120.06 (14)
C29—C30—C31122.71 (12)C116—C115—H115120.0
C29—C30—H30118.6C114—C115—H115120.0
C31—C30—H30118.6C117—C116—C115119.00 (13)
C32—C31—C30120.22 (13)C117—C116—H116120.5
C32—C31—H31119.9C115—C116—H116120.5
C30—C31—H31119.9C116—C117—C118120.33 (15)
C31—C32—C33118.75 (12)C116—C117—H117119.8
C31—C32—H32120.6C118—C117—H117119.8
C33—C32—H32120.6C117—C118—C113122.83 (14)
C34—C33—C32120.11 (12)C117—C118—H118118.6
C34—C33—H33119.9C113—C118—H118118.6
C32—C33—H33119.9C124—C119—C120115.20 (11)
C33—C34—C29122.94 (12)C124—C119—B4124.58 (11)
C33—C34—H34118.5C120—C119—B4120.06 (11)
C29—C34—H34118.5C121—C120—C119122.98 (12)
C40—C35—C36115.24 (11)C121—C120—H120118.5
C40—C35—B1124.61 (11)C119—C120—H120118.5
C36—C35—B1120.15 (11)C120—C121—C122120.17 (12)
C37—C36—C35122.97 (12)C120—C121—H121119.9
C37—C36—H36118.5C122—C121—H121119.9
C35—C36—H36118.5C123—C122—C121118.91 (12)
C38—C37—C36119.82 (13)C123—C122—H122120.5
C38—C37—H37120.1C121—C122—H122120.5
C36—C37—H37120.1C122—C123—C124120.16 (12)
C39—C38—C37119.24 (12)C122—C123—H123119.9
C39—C38—H38120.4C124—C123—H123119.9
C37—C38—H38120.4C123—C124—C119122.56 (12)
C38—C39—C40120.11 (13)C123—C124—H124118.7
C38—C39—H39119.9C119—C124—H124118.7
C40—C39—H39119.9
C2—N1—C1—N2150.64 (12)C53—B2—C65—C701.46 (16)
C3—N1—C1—N231.40 (18)C59—B2—C65—C70118.21 (13)
C2—N1—C1—N330.51 (18)C71—B2—C65—C6656.32 (14)
C3—N1—C1—N3147.45 (12)C53—B2—C65—C66177.67 (11)
C5—N2—C1—N1144.00 (13)C59—B2—C65—C6665.58 (14)
C4—N2—C1—N132.01 (18)C70—C65—C66—C671.27 (19)
C5—N2—C1—N334.86 (18)B2—C65—C66—C67177.83 (12)
C4—N2—C1—N3149.13 (12)C65—C66—C67—C680.9 (2)
C6—N3—C1—N139.40 (17)C66—C67—C68—C690.3 (2)
C7—N3—C1—N1139.38 (12)C67—C68—C69—C701.0 (2)
C6—N3—C1—N2139.47 (12)C68—C69—C70—C650.6 (2)
C7—N3—C1—N241.75 (17)C66—C65—C70—C690.53 (18)
C1—N3—C7—C8102.31 (14)B2—C65—C70—C69176.91 (12)
C6—N3—C7—C876.52 (14)C53—B2—C71—C76122.14 (12)
C11—N4—C8—C757.35 (15)C65—B2—C71—C76116.68 (13)
C9—N4—C8—C765.30 (15)C59—B2—C71—C765.09 (17)
C10—N4—C8—C7176.57 (13)C53—B2—C71—C7262.48 (14)
N3—C7—C8—N4131.18 (11)C65—B2—C71—C7258.70 (14)
N6A—C12A—N5A—C13A144.2 (2)C59—B2—C71—C72179.54 (11)
N7A—C12A—N5A—C13A34.1 (4)C76—C71—C72—C731.53 (18)
N6A—C12A—N5A—C14A32.3 (4)B2—C71—C72—C73177.33 (12)
N7A—C12A—N5A—C14A149.4 (2)C71—C72—C73—C742.0 (2)
N5A—C12A—N6A—C16A145.0 (3)C72—C73—C74—C750.4 (2)
N7A—C12A—N6A—C16A36.7 (4)C73—C74—C75—C761.4 (2)
N5A—C12A—N6A—C15A34.6 (4)C74—C75—C76—C711.9 (2)
N7A—C12A—N6A—C15A143.7 (2)C72—C71—C76—C750.38 (18)
N5A—C12A—N7A—C18A40.8 (4)B2—C71—C76—C75175.20 (12)
N6A—C12A—N7A—C18A140.9 (2)C83—B3—C77—C7814.10 (16)
N5A—C12A—N7A—C17A147.7 (2)C95—B3—C77—C78105.54 (13)
N6A—C12A—N7A—C17A30.6 (4)C89—B3—C77—C78135.70 (12)
C12A—N7A—C18A—C1979.8 (2)C83—B3—C77—C82168.40 (11)
C17A—N7A—C18A—C1992.35 (14)C95—B3—C77—C8271.96 (14)
N6B—C12B—N5B—C14B20 (8)C89—B3—C77—C8246.80 (15)
N7B—C12B—N5B—C14B142 (6)C82—C77—C78—C790.82 (18)
N6B—C12B—N5B—C13B145 (3)B3—C77—C78—C79178.48 (11)
N7B—C12B—N5B—C13B53 (6)C77—C78—C79—C800.4 (2)
N5B—C12B—N6B—C15B61 (5)C78—C79—C80—C810.3 (2)
N7B—C12B—N6B—C15B137 (3)C79—C80—C81—C820.5 (2)
N5B—C12B—N6B—C16B138 (3)C80—C81—C82—C770.1 (2)
N7B—C12B—N6B—C16B24 (6)C78—C77—C82—C810.56 (18)
N5B—C12B—N7B—C18B32 (6)B3—C77—C82—C81178.30 (12)
N6B—C12B—N7B—C18B130 (3)C95—B3—C83—C8810.63 (16)
N5B—C12B—N7B—C17B148 (3)C89—B3—C83—C88108.13 (13)
N6B—C12B—N7B—C17B50 (5)C77—B3—C83—C88130.55 (12)
C12B—N7B—C18B—C1935 (5)C95—B3—C83—C84168.36 (11)
C17B—N7B—C18B—C19145 (3)C89—B3—C83—C8472.88 (14)
C22—N8—C19—C18A52.23 (14)C77—B3—C83—C8448.44 (14)
C20—N8—C19—C18A69.49 (14)C88—C83—C84—C851.55 (18)
C21—N8—C19—C18A172.42 (11)B3—C83—C84—C85177.53 (11)
C22—N8—C19—C18B37.6 (14)C83—C84—C85—C860.81 (19)
C20—N8—C19—C18B84.1 (14)C84—C85—C86—C870.34 (19)
C21—N8—C19—C18B157.8 (14)C85—C86—C87—C880.65 (19)
N7A—C18A—C19—N8160.91 (11)C86—C87—C88—C830.17 (19)
N7B—C18B—C19—N8161 (2)C84—C83—C88—C871.23 (18)
C35—B1—C29—C30106.58 (13)B3—C83—C88—C87177.82 (11)
C47—B1—C29—C30134.61 (12)C83—B3—C89—C9418.18 (16)
C41—B1—C29—C3012.50 (16)C95—B3—C89—C94137.27 (12)
C35—B1—C29—C3474.54 (14)C77—B3—C89—C94103.34 (13)
C47—B1—C29—C3444.28 (14)C83—B3—C89—C90161.99 (11)
C41—B1—C29—C34166.39 (11)C95—B3—C89—C9042.90 (14)
C34—C29—C30—C310.55 (19)C77—B3—C89—C9076.49 (13)
B1—C29—C30—C31178.37 (12)C94—C89—C90—C911.55 (18)
C29—C30—C31—C320.4 (2)B3—C89—C90—C91178.30 (11)
C30—C31—C32—C330.9 (2)C89—C90—C91—C920.3 (2)
C31—C32—C33—C340.5 (2)C90—C91—C92—C930.84 (19)
C32—C33—C34—C290.5 (2)C91—C92—C93—C940.54 (19)
C30—C29—C34—C330.97 (19)C92—C93—C94—C890.9 (2)
B1—C29—C34—C33178.02 (12)C90—C89—C94—C931.86 (18)
C29—B1—C35—C400.87 (16)B3—C89—C94—C93177.98 (11)
C47—B1—C35—C40114.50 (13)C83—B3—C95—C10099.79 (13)
C41—B1—C35—C40122.34 (12)C89—B3—C95—C100140.25 (11)
C29—B1—C35—C36179.91 (11)C77—B3—C95—C10020.60 (16)
C47—B1—C35—C3664.72 (14)C83—B3—C95—C9676.06 (14)
C41—B1—C35—C3658.44 (14)C89—B3—C95—C9643.89 (14)
C40—C35—C36—C372.85 (18)C77—B3—C95—C96163.54 (11)
B1—C35—C36—C37176.44 (12)C100—C95—C96—C970.81 (18)
C35—C36—C37—C381.4 (2)B3—C95—C96—C97175.40 (12)
C36—C37—C38—C391.0 (2)C95—C96—C97—C980.5 (2)
C37—C38—C39—C401.7 (2)C96—C97—C98—C990.09 (19)
C38—C39—C40—C350.2 (2)C97—C98—C99—C1000.35 (19)
C36—C35—C40—C392.06 (18)C98—C99—C100—C950.02 (19)
B1—C35—C40—C39177.19 (12)C96—C95—C100—C990.54 (18)
C35—B1—C41—C46132.49 (12)B3—C95—C100—C99175.50 (11)
C29—B1—C41—C46106.47 (13)C107—B4—C101—C102127.47 (12)
C47—B1—C41—C4610.85 (17)C119—B4—C101—C1027.48 (16)
C35—B1—C41—C4245.94 (14)C113—B4—C101—C102110.97 (13)
C29—B1—C41—C4275.10 (14)C107—B4—C101—C10654.67 (14)
C47—B1—C41—C42167.58 (11)C119—B4—C101—C106174.66 (10)
C46—C41—C42—C430.31 (18)C113—B4—C101—C10666.90 (14)
B1—C41—C42—C43178.89 (11)C106—C101—C102—C1032.56 (18)
C41—C42—C43—C440.8 (2)B4—C101—C102—C103175.40 (12)
C42—C43—C44—C450.48 (19)C101—C102—C103—C1040.1 (2)
C43—C44—C45—C460.24 (19)C102—C103—C104—C1051.92 (19)
C44—C45—C46—C410.7 (2)C103—C104—C105—C1061.35 (19)
C42—C41—C46—C450.44 (18)C104—C105—C106—C1011.3 (2)
B1—C41—C46—C45178.06 (12)C102—C101—C106—C1053.16 (18)
C35—B1—C47—C520.78 (16)B4—C101—C106—C105174.92 (11)
C29—B1—C47—C52119.78 (12)C101—B4—C107—C11232.99 (15)
C41—B1—C47—C52119.10 (13)C119—B4—C107—C11289.35 (13)
C35—B1—C47—C48172.97 (11)C113—B4—C107—C112154.72 (11)
C29—B1—C47—C4853.97 (14)C101—B4—C107—C108154.15 (11)
C41—B1—C47—C4867.14 (14)C119—B4—C107—C10883.50 (13)
C52—C47—C48—C490.08 (18)C113—B4—C107—C10832.43 (15)
B1—C47—C48—C49174.24 (12)C112—C107—C108—C1090.75 (18)
C47—C48—C49—C500.1 (2)B4—C107—C108—C109172.57 (12)
C48—C49—C50—C510.2 (2)C107—C108—C109—C1100.4 (2)
C49—C50—C51—C520.5 (2)C108—C109—C110—C1110.03 (19)
C48—C47—C52—C510.28 (18)C109—C110—C111—C1120.12 (18)
B1—C47—C52—C51174.33 (12)C110—C111—C112—C1070.56 (19)
C50—C51—C52—C470.6 (2)C108—C107—C112—C1110.85 (17)
C71—B2—C53—C544.45 (16)B4—C107—C112—C111172.48 (11)
C65—B2—C53—C54121.97 (12)C107—B4—C113—C11892.34 (14)
C59—B2—C53—C54116.99 (12)C101—B4—C113—C11828.96 (16)
C71—B2—C53—C58179.16 (10)C119—B4—C113—C118150.72 (12)
C65—B2—C53—C5861.64 (14)C107—B4—C113—C11486.36 (13)
C59—B2—C53—C5859.40 (13)C101—B4—C113—C114152.35 (11)
C58—C53—C54—C550.36 (17)C119—B4—C113—C11430.58 (15)
B2—C53—C54—C55176.90 (11)C118—C113—C114—C1150.40 (19)
C53—C54—C55—C560.01 (19)B4—C113—C114—C115179.21 (12)
C54—C55—C56—C570.47 (19)C113—C114—C115—C1160.5 (2)
C55—C56—C57—C580.54 (19)C114—C115—C116—C1170.0 (2)
C56—C57—C58—C530.14 (19)C115—C116—C117—C1180.7 (2)
C54—C53—C58—C570.30 (17)C116—C117—C118—C1130.9 (2)
B2—C53—C58—C57177.05 (11)C114—C113—C118—C1170.31 (19)
C71—B2—C59—C64117.37 (14)B4—C113—C118—C117178.45 (13)
C53—B2—C59—C64121.39 (13)C107—B4—C119—C1240.16 (16)
C65—B2—C59—C640.58 (18)C101—B4—C119—C124121.09 (12)
C71—B2—C59—C6067.00 (15)C113—B4—C119—C124118.15 (12)
C53—B2—C59—C6054.24 (14)C107—B4—C119—C120175.25 (10)
C65—B2—C59—C60175.05 (11)C101—B4—C119—C12063.82 (14)
C64—C59—C60—C611.57 (19)C113—B4—C119—C12056.94 (14)
B2—C59—C60—C61174.51 (12)C124—C119—C120—C1210.35 (18)
C59—C60—C61—C620.2 (2)B4—C119—C120—C121175.18 (11)
C60—C61—C62—C631.3 (2)C119—C120—C121—C1220.92 (19)
C61—C62—C63—C641.3 (2)C120—C121—C122—C1231.45 (19)
C60—C59—C64—C631.5 (2)C121—C122—C123—C1240.73 (19)
B2—C59—C64—C63174.30 (13)C122—C123—C124—C1190.58 (19)
C62—C63—C64—C590.1 (2)C120—C119—C124—C1231.09 (17)
C71—B2—C65—C70119.89 (13)B4—C119—C124—C123174.21 (11)
Hydrogen-bond geometry (Å, º) top
The ring centroids are defined as follows: Cg1 = C53–C58, Cg2 = C65–C70, Cg3 = C71–C76, Cg4 = C89–C94, Cg5 = C95–C100, Cg6 = C29–C34, Cg7 = C41–C46, Cg8 = C101–C106, Cg9 = C107–C112 and Cg10 = C113–C118.
D—H···AD—HH···AD···AD—H···A
C13B—H13E···O10.982.613.513 (2)153
C17A—H17C···O10.982.413.369 (2)167
C19—H19A···O10.992.373.290 (2)154
C20—H20C···O10.982.463.323 (2)147
C6—H6A···O20.982.503.467 (2)170
C8—H8B···O20.992.553.449 (2)152
C9—H9B···O20.982.523.417 (2)152
C4—H4B···Cg10.983.023.881 (2)146
C21—H21B···Cg10.982.743.713 (2)171
C3—H3C···Cg2i0.982.883.739 (2)147
C13A—H13A···Cg30.982.753.587 (2)144
C27—H27C···Cg3ii0.982.943.629 (2)128
C28—H28B···Cg4ii0.982.843.554 (2)130
C6—H6B···Cg5iii0.982.673.614 (2)162
C8—H8A···Cg60.992.933.854 (2)155
C4—H4C···Cg70.982.763.669 (2)154
C24—H24B···Cg80.983.053.681 (2)124
C18A—H18A···Cg9iv0.992.713.512 (2)139
C18B—H18C···Cg9iv0.992.873.662 (2)138
C25—H25C···Cg10v0.982.683.653 (2)175
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x+1, y+2, z; (iv) x+1, y+1, z+1; (v) x1, y1, z.
 

Acknowledgements

The authors thank Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for measuring the diffraction data.

References

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