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ISSN: 2056-9890

Crystal structure of 2-di­methyl­amino-1-eth­­oxy­carbonyl-3-methyl-3,4,5,6-tetra­hydro­pyrimidin-1-ium tetra­phenyl­borate

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 7 October 2015; accepted 22 October 2015; online 31 October 2015)

The asymmetric unit of the title salt, C10H20N3O2+·C24H20B, contains two cations and two tetra­phenyl­borate ions. The C—N bond lengths in the central CN3 unit of the guanidinium ions range between 1.323 (2) and 1.381 (2) Å, indicating partial double-bond character. The central C atoms are bonded to the three N atoms in a nearly ideal trigonal–planar geometry and the positive charge is delocalized in the CN3 plane. The cationic six-membered rings are nonplanar, the dihedral angles between the N/C/N and C/C/C planes ranging from 45.8 (1) to 53.6 (1)°. In the crystal, C—H⋯π inter­actions are present between the guanidinium H atoms and the phenyl rings of the tetra­phenyl­borate ions. The phenyl rings form aromatic pockets, in which the guanidinium ions are embedded.

1. Related literature

For the crystal structures of alkali metal tetra­phenyl­borates, see: Behrens et al. (2012[Behrens, U., Hoffmann, F. & Olbrich, F. (2012). Organometallics, 31, 905-913.]). For the crystal structure of 2-di­methyl­amino-1-(2-eth­oxy-2-oxoeth­yl)-3-methyl-3,4,5,6-tetra­hydro­pyrimidin-1-ium tetra­phenyl­borate, see: Tiritiris & Kantlehner (2012a[Tiritiris, I. & Kantlehner, W. (2012a). Acta Cryst. E68, o2002.]). For the crystal structure of 1-benzyl-2-di­methyl­amino-3-methyl-3,4,5,6-tetra­hydro­pyrimidin-1-ium bromide, see: Tiritiris & Kantlehner, 2012b[Tiritiris, I. & Kantlehner, W. (2012b). Acta Cryst. E68, o2308.].

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C10H20N3O2+·C24H20B

  • Mr = 533.50

  • Monoclinic P 21 /c

  • a = 18.5710 (5) Å

  • b = 19.2164 (7) Å

  • c = 18.6107 (5) Å

  • β = 119.280 (2)°

  • V = 5793.0 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.24 × 0.17 × 0.12 mm

2.2. Data collection

  • Bruker–Nonius KappaCCD diffractometer

  • 26283 measured reflections

  • 14001 independent reflections

  • 9686 reflections with I > 2σ(I)

  • Rint = 0.058

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.119

  • S = 1.04

  • 14001 reflections

  • 729 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C21–C26, C27–C32, C45–C50, C51–C56, C57–C62 and C63–C68 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5ACg1 0.99 2.77 3.502 (3) 131
C19—H19BCg1 0.99 2.86 3.559 (3) 128
C17—H17BCg2 0.99 2.67 3.632 (3) 165
C6—H6BCg3 0.99 2.75 3.624 (3) 147
C13—H13CCg3 0.98 2.72 3.421 (3) 129
C13—H13BCg4 0.98 2.67 3.583 (3) 154
C12—H12CCg5 0.98 2.70 3.329 (3) 121
C14—H14BCg5 0.98 2.76 3.354 (3) 120
C12—H12BCg6 0.98 2.64 3.535 (3) 151
C9—H9ACg6 0.99 2.75 3.655 (3) 151

Data collection: COLLECT (Hooft, 2004[Hooft, R. W. W. (2004). COLLECT. Bruker-Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (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.]); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL2014.

Supporting information


Comment top

The cation in the title compound is similar to the cations in the structurally known compounds 2-dimethylamino-1-ethoxycarbonyl-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate (Tiritiris & Kantlehner, 2012a) and 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide (Tiritiris & Kantlehner, 2012b). The asymmetric unit contains two cations and two tetraphenylborate ions. Prominent bond parameters in the guanidinium ions are: C1–N1 = 1.323 (2) Å, C1–N2 = 1.333 (2) Å, C1–N3 = 1.379 (2) Å (cation I) and C11–N4 = 1.326 (2) Å, C11–N5 = 1.324 (2) Å, C11–N6 = 1.381 (2) Å (cation II). The N–C–N angles are in a range from 116.8 (2)° to 122.7 (2)°, indicating nearly ideal trigonal-planar surroundings of the carbon centres C1 and C11 by the nitrogen atoms. The positive charge is completely delocalized in the CN3 plane. The cyclic guanidinium ions are non planar (Fig. 1). The carbon atoms C6 and C16 are not in the ring plane. The dihedral angle between the planes N3/C1/N2 and C5/C6/C7 is 53.6 (1)°, the dihedral angle between the planes N5/C11/N6 and C15/C16/C17 is 45.8 (1)°. These values are comparable with those determined for the guanidinium ions in 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate [49.9 (1)°] (Tiritiris & Kantlehner, 2012a) and 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide [55.0 (3)°] (Tiritiris & Kantlehner, 2012b). The bond lengths and angles in the tetraphenylborate ions are in good agreement with the data from the crystal structure analysis of the alkali metal tetraphenylborates (Behrens et al., 2012). C–H···π interactions between the guanidinium hydrogen atoms of –N(CH3)2 and –CH2 groups and the phenyl carbon atoms (centroids) of the tetraphenylborate ion are present (Fig. 2 and 3), ranging from 2.64 to 2.86 Å (Tab. 1). The phenyl rings form aromatic pockets, in which the guanidinium ions are embedded.

Related literature top

For the crystal structures of alkali metal tetraphenylborates, see: Behrens et al. (2012). For the crystal structure of 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate, see: Tiritiris & Kantlehner (2012a). For the crystal structure of 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide, see: Tiritiris & Kantlehner, 2012b.

Experimental top

The title compound was obtained by reaction of 1-methyl-2-dimethylamino-1,4,5,6-tetrahydropyrimidine with chloroformic acid ethyl ester in acetonitrile for one hour at room temperature. After evaporation of the solvent the crude 2-dimethylamino-1-(2-ethoxy-2-oxomethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium chloride (I) was washed with diethylether and dried in vacuo. 1.0 g (4.0 mmol) of (I) was dissolved in 20 ml acetonitrile and 1.37 g (4.0 mmol) of sodium tetraphenylborate in 10 ml acetonitrile was added. After stirring for one hour at room temperature, the precipitated sodium chloride was filtered off. The title compound crystallized from a saturated acetonitrile solution after several days at 273 K, forming colorless single crystals. Yield: 1.67 g (77.5%).

Refinement top

The hydrogen atoms of the methyl groups were allowed to rotate with a fixed angle around the C–N and C–C bonds to best fit the experimental electron density, with Uiso(H) set to 1.5 Ueq(C) and d(C—H) = 0.98 Å. The remaining H atoms were placed in calculated positions with d(C—H) = 0.99 Å (H atoms in CH2 groups) and (C—H) = 0.95 Å (H atoms in aromatic rings). They were refined using a riding model, with Uiso(H) set to 1.2Ueq(C).

Structure description top

The cation in the title compound is similar to the cations in the structurally known compounds 2-dimethylamino-1-ethoxycarbonyl-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate (Tiritiris & Kantlehner, 2012a) and 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide (Tiritiris & Kantlehner, 2012b). The asymmetric unit contains two cations and two tetraphenylborate ions. Prominent bond parameters in the guanidinium ions are: C1–N1 = 1.323 (2) Å, C1–N2 = 1.333 (2) Å, C1–N3 = 1.379 (2) Å (cation I) and C11–N4 = 1.326 (2) Å, C11–N5 = 1.324 (2) Å, C11–N6 = 1.381 (2) Å (cation II). The N–C–N angles are in a range from 116.8 (2)° to 122.7 (2)°, indicating nearly ideal trigonal-planar surroundings of the carbon centres C1 and C11 by the nitrogen atoms. The positive charge is completely delocalized in the CN3 plane. The cyclic guanidinium ions are non planar (Fig. 1). The carbon atoms C6 and C16 are not in the ring plane. The dihedral angle between the planes N3/C1/N2 and C5/C6/C7 is 53.6 (1)°, the dihedral angle between the planes N5/C11/N6 and C15/C16/C17 is 45.8 (1)°. These values are comparable with those determined for the guanidinium ions in 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate [49.9 (1)°] (Tiritiris & Kantlehner, 2012a) and 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide [55.0 (3)°] (Tiritiris & Kantlehner, 2012b). The bond lengths and angles in the tetraphenylborate ions are in good agreement with the data from the crystal structure analysis of the alkali metal tetraphenylborates (Behrens et al., 2012). C–H···π interactions between the guanidinium hydrogen atoms of –N(CH3)2 and –CH2 groups and the phenyl carbon atoms (centroids) of the tetraphenylborate ion are present (Fig. 2 and 3), ranging from 2.64 to 2.86 Å (Tab. 1). The phenyl rings form aromatic pockets, in which the guanidinium ions are embedded.

For the crystal structures of alkali metal tetraphenylborates, see: Behrens et al. (2012). For the crystal structure of 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate, see: Tiritiris & Kantlehner (2012a). For the crystal structure of 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide, see: Tiritiris & Kantlehner, 2012b.

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (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).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with displacement ellipsoids at the 50% probability level. All hydrogen atoms were omitted for the sake of clarity.
[Figure 2] Fig. 2. C—H···π interactions (brown dashed lines) between the hydrogen atoms of the guanidinium ion and the phenyl carbon atoms (centroids) of the tetraphenylborate ion (anion I).
[Figure 3] Fig. 3. C—H···π interactions (brown dashed lines) between the hydrogen atoms of the guanidinium ion and the phenyl carbon atoms (centroids) of the tetraphenylborate ion (anion II).
2-Dimethylamino-1-ethoxycarbonyl-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate top
Crystal data top
C10H20N3O2+·C24H20BF(000) = 2288
Mr = 533.50Dx = 1.223 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 26101 reflections
a = 18.5710 (5) Åθ = 1.3–28.1°
b = 19.2164 (7) ŵ = 0.08 mm1
c = 18.6107 (5) ÅT = 100 K
β = 119.280 (2)°Block, colorless
V = 5793.0 (3) Å30.24 × 0.17 × 0.12 mm
Z = 8
Data collection top
Bruker–Nonius KappaCCD
diffractometer
9686 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.058
Graphite monochromatorθmax = 28.2°, θmin = 1.3°
φ scans, and ω scansh = 2424
26283 measured reflectionsk = 2523
14001 independent reflectionsl = 2424
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0219P)2 + 5.1462P]
where P = (Fo2 + 2Fc2)/3
14001 reflections(Δ/σ)max < 0.001
729 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C10H20N3O2+·C24H20BV = 5793.0 (3) Å3
Mr = 533.50Z = 8
Monoclinic, P21/cMo Kα radiation
a = 18.5710 (5) ŵ = 0.08 mm1
b = 19.2164 (7) ÅT = 100 K
c = 18.6107 (5) Å0.24 × 0.17 × 0.12 mm
β = 119.280 (2)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
9686 reflections with I > 2σ(I)
26283 measured reflectionsRint = 0.058
14001 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.04Δρmax = 0.50 e Å3
14001 reflectionsΔρmin = 0.25 e Å3
729 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.79842 (9)0.55416 (8)0.00502 (9)0.0141 (3)
N20.81433 (9)0.67471 (8)0.00009 (9)0.0157 (3)
N30.72182 (9)0.62582 (8)0.03487 (9)0.0135 (3)
C10.77986 (10)0.61714 (9)0.00972 (10)0.0129 (3)
C20.87832 (12)0.53755 (11)0.00129 (11)0.0204 (4)
H2A0.87110.53010.05400.031*
H2B0.90060.49520.03420.031*
H2C0.91670.57620.02790.031*
C30.74394 (12)0.49416 (9)0.02357 (12)0.0195 (4)
H3A0.76670.46250.02380.029*
H3B0.73950.46970.07180.029*
H3C0.68910.50990.03510.029*
C40.83819 (13)0.68127 (11)0.06387 (12)0.0214 (4)
H4A0.81890.64040.09990.032*
H4B0.89840.68450.03800.032*
H4C0.81320.72330.09640.032*
C50.79627 (12)0.73980 (10)0.03049 (12)0.0207 (4)
H5A0.82290.77990.01930.025*
H5B0.81720.73690.09060.025*
C60.70353 (12)0.74823 (10)0.01491 (12)0.0216 (4)
H6A0.68260.74840.07510.026*
H6B0.68810.79290.00050.026*
C70.66602 (11)0.68779 (9)0.00827 (11)0.0156 (4)
H7A0.65580.70230.05360.019*
H7B0.61230.67510.03970.019*
C80.71983 (11)0.58034 (9)0.09302 (11)0.0142 (3)
O10.77527 (8)0.54207 (7)0.13625 (8)0.0191 (3)
O20.64801 (8)0.58761 (7)0.09186 (8)0.0184 (3)
C90.63793 (12)0.54654 (10)0.15269 (12)0.0190 (4)
H9A0.59750.56970.16500.023*
H9B0.69130.54390.20450.023*
C100.60852 (13)0.47449 (11)0.12107 (13)0.0257 (4)
H10A0.55530.47710.07020.039*
H10B0.60200.44790.16250.039*
H10C0.64900.45130.10980.039*
N40.63551 (9)0.36665 (8)0.40962 (9)0.0135 (3)
N50.73941 (10)0.38338 (8)0.54432 (9)0.0182 (3)
N60.77452 (9)0.36757 (8)0.44206 (9)0.0150 (3)
C110.71453 (11)0.37415 (9)0.46510 (10)0.0124 (3)
C120.60942 (11)0.32737 (10)0.33341 (11)0.0170 (4)
H12A0.59360.35980.28750.025*
H12B0.56210.29800.32270.025*
H12C0.65510.29800.33910.025*
C130.56893 (11)0.40535 (10)0.41317 (11)0.0167 (4)
H13A0.53410.37290.42320.025*
H13B0.53540.42940.36070.025*
H13C0.59300.43950.45790.025*
C140.68755 (14)0.36456 (12)0.58036 (12)0.0276 (5)
H14A0.66200.40660.58780.041*
H14B0.72150.34220.63390.041*
H14C0.64440.33220.54360.041*
C150.82339 (12)0.40587 (12)0.60501 (12)0.0268 (5)
H15A0.84530.37400.65290.032*
H15B0.82040.45300.62480.032*
C160.88247 (13)0.40729 (11)0.57137 (13)0.0273 (5)
H16A0.87960.45290.54530.033*
H16B0.93970.40020.61640.033*
C170.85854 (11)0.35009 (10)0.50887 (11)0.0174 (4)
H17A0.89770.34770.48720.021*
H17B0.85840.30460.53380.021*
C180.76607 (11)0.40591 (9)0.37379 (10)0.0144 (3)
O30.70768 (8)0.44185 (7)0.33087 (7)0.0180 (3)
O40.83231 (8)0.39572 (7)0.36536 (8)0.0181 (3)
C190.83792 (12)0.43919 (10)0.30418 (11)0.0174 (4)
H19A0.78270.44340.25490.021*
H19B0.87540.41710.28720.021*
C200.86987 (13)0.51034 (10)0.33867 (12)0.0224 (4)
H20A0.83030.53380.35090.034*
H20B0.87710.53770.29820.034*
H20C0.92300.50590.38930.034*
B10.98280 (12)0.63490 (10)0.78042 (11)0.0113 (4)
C210.98217 (10)0.64626 (9)0.69255 (10)0.0125 (3)
C221.01083 (11)0.70816 (10)0.67468 (11)0.0158 (4)
H221.03410.74300.71610.019*
C231.00657 (11)0.72050 (10)0.59924 (11)0.0193 (4)
H231.02780.76260.59030.023*
C240.97130 (11)0.67145 (10)0.53708 (10)0.0176 (4)
H240.96840.67940.48540.021*
C250.94022 (11)0.61059 (10)0.55120 (11)0.0178 (4)
H250.91480.57700.50860.021*
C260.94618 (11)0.59863 (9)0.62756 (10)0.0145 (3)
H260.92490.55630.63600.017*
C271.07086 (10)0.65452 (9)0.86183 (10)0.0122 (3)
C281.14423 (11)0.67309 (9)0.86286 (10)0.0147 (3)
H281.14430.67600.81190.018*
C291.21742 (11)0.68755 (9)0.93552 (11)0.0169 (4)
H291.26580.70000.93330.020*
C301.21940 (11)0.68370 (9)1.01061 (11)0.0163 (4)
H301.26880.69371.06030.020*
C311.14793 (11)0.66496 (9)1.01231 (11)0.0170 (4)
H311.14840.66171.06350.020*
C321.07584 (11)0.65097 (9)0.93950 (10)0.0149 (3)
H321.02780.63850.94230.018*
C330.90974 (10)0.68769 (9)0.77216 (10)0.0114 (3)
C340.82648 (11)0.67327 (9)0.71577 (10)0.0141 (3)
H340.81330.63070.68620.017*
C350.76280 (11)0.71868 (10)0.70163 (11)0.0169 (4)
H350.70740.70650.66360.020*
C360.77995 (11)0.78203 (10)0.74298 (11)0.0186 (4)
H360.73670.81340.73380.022*
C370.86115 (12)0.79827 (10)0.79769 (11)0.0198 (4)
H370.87400.84170.82560.024*
C380.92447 (11)0.75190 (9)0.81246 (11)0.0156 (4)
H380.97960.76430.85120.019*
C390.96464 (10)0.55282 (9)0.79114 (10)0.0125 (3)
C401.01674 (11)0.50062 (10)0.78853 (11)0.0168 (4)
H401.06130.51410.78010.020*
C411.00571 (12)0.43049 (10)0.79772 (11)0.0197 (4)
H411.04170.39700.79450.024*
C420.94228 (13)0.40910 (10)0.81155 (11)0.0220 (4)
H420.93430.36110.81750.026*
C430.89074 (12)0.45828 (10)0.81660 (11)0.0194 (4)
H430.84750.44420.82680.023*
C440.90227 (11)0.52917 (9)0.80670 (11)0.0161 (4)
H440.86640.56230.81070.019*
B20.46587 (12)0.61087 (10)0.28109 (11)0.0103 (4)
C450.54736 (10)0.59612 (9)0.37117 (10)0.0128 (3)
C460.62523 (11)0.57874 (9)0.38126 (11)0.0172 (4)
H460.63250.57830.33420.021*
C470.69209 (11)0.56207 (10)0.45750 (12)0.0220 (4)
H470.74390.55090.46180.026*
C480.68321 (12)0.56176 (10)0.52710 (12)0.0243 (4)
H480.72890.55090.57940.029*
C490.60724 (13)0.57734 (10)0.51991 (11)0.0225 (4)
H490.60030.57660.56720.027*
C500.54087 (11)0.59417 (10)0.44328 (11)0.0174 (4)
H500.48920.60480.43960.021*
C510.42408 (10)0.53399 (9)0.24948 (10)0.0118 (3)
C520.45417 (11)0.48859 (9)0.21120 (10)0.0156 (4)
H520.49610.50470.20010.019*
C530.42506 (12)0.42088 (10)0.18881 (11)0.0202 (4)
H530.44720.39190.16300.024*
C540.36389 (12)0.39573 (10)0.20406 (11)0.0233 (4)
H540.34330.34980.18810.028*
C550.33328 (12)0.43817 (10)0.24267 (11)0.0217 (4)
H550.29210.42110.25440.026*
C560.36271 (11)0.50610 (10)0.26462 (11)0.0167 (4)
H560.34040.53450.29070.020*
C570.40442 (10)0.66896 (9)0.28797 (10)0.0115 (3)
C580.31882 (11)0.67108 (9)0.23425 (10)0.0138 (3)
H580.29380.63430.19580.017*
C590.26885 (11)0.72536 (10)0.23514 (11)0.0177 (4)
H590.21120.72490.19780.021*
C600.30362 (12)0.77975 (10)0.29049 (11)0.0192 (4)
H600.27010.81660.29160.023*
C610.38795 (12)0.77961 (10)0.34415 (11)0.0179 (4)
H610.41260.81670.38220.021*
C620.43671 (11)0.72523 (9)0.34240 (10)0.0152 (4)
H620.49440.72640.37980.018*
C630.48849 (10)0.64604 (9)0.21412 (10)0.0118 (3)
C640.55235 (11)0.69427 (9)0.23561 (11)0.0160 (4)
H640.58890.70290.29240.019*
C650.56471 (11)0.73023 (10)0.17738 (12)0.0190 (4)
H650.60840.76300.19480.023*
C660.51356 (12)0.71822 (10)0.09466 (12)0.0197 (4)
H660.52190.74210.05460.024*
C670.44959 (11)0.67064 (10)0.07073 (11)0.0190 (4)
H670.41380.66190.01380.023*
C680.43761 (11)0.63595 (10)0.12913 (11)0.0155 (3)
H680.39310.60390.11100.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0144 (7)0.0150 (7)0.0125 (7)0.0008 (6)0.0063 (6)0.0005 (6)
N20.0193 (8)0.0144 (7)0.0170 (7)0.0027 (6)0.0116 (6)0.0031 (6)
N30.0141 (7)0.0123 (7)0.0149 (7)0.0010 (6)0.0078 (6)0.0015 (6)
C10.0129 (8)0.0149 (8)0.0080 (7)0.0009 (7)0.0028 (7)0.0005 (6)
C20.0196 (9)0.0250 (10)0.0174 (9)0.0078 (8)0.0096 (8)0.0017 (7)
C30.0242 (10)0.0123 (9)0.0193 (9)0.0006 (7)0.0086 (8)0.0030 (7)
C40.0281 (10)0.0217 (10)0.0213 (9)0.0056 (8)0.0175 (8)0.0019 (8)
C50.0266 (10)0.0138 (9)0.0270 (10)0.0057 (7)0.0171 (9)0.0070 (7)
C60.0286 (10)0.0133 (9)0.0267 (10)0.0034 (8)0.0164 (9)0.0018 (7)
C70.0150 (9)0.0123 (8)0.0187 (9)0.0025 (7)0.0075 (7)0.0006 (7)
C80.0170 (9)0.0112 (8)0.0165 (8)0.0011 (7)0.0098 (7)0.0014 (6)
O10.0203 (7)0.0209 (7)0.0179 (6)0.0054 (5)0.0108 (6)0.0053 (5)
O20.0187 (7)0.0171 (7)0.0243 (7)0.0026 (5)0.0144 (6)0.0062 (5)
C90.0219 (10)0.0184 (9)0.0245 (9)0.0015 (7)0.0174 (8)0.0048 (7)
C100.0275 (11)0.0218 (10)0.0284 (10)0.0031 (8)0.0142 (9)0.0038 (8)
N40.0144 (7)0.0141 (7)0.0140 (7)0.0013 (6)0.0085 (6)0.0030 (6)
N50.0192 (8)0.0233 (8)0.0123 (7)0.0010 (6)0.0079 (6)0.0004 (6)
N60.0123 (7)0.0188 (8)0.0133 (7)0.0021 (6)0.0056 (6)0.0030 (6)
C110.0153 (8)0.0084 (8)0.0134 (8)0.0020 (6)0.0069 (7)0.0023 (6)
C120.0159 (9)0.0183 (9)0.0173 (8)0.0027 (7)0.0086 (7)0.0061 (7)
C130.0136 (9)0.0192 (9)0.0193 (9)0.0004 (7)0.0097 (7)0.0023 (7)
C140.0363 (12)0.0346 (12)0.0204 (9)0.0095 (9)0.0204 (9)0.0105 (9)
C150.0231 (10)0.0330 (11)0.0142 (9)0.0029 (9)0.0012 (8)0.0061 (8)
C160.0214 (10)0.0223 (10)0.0273 (10)0.0032 (8)0.0033 (9)0.0020 (8)
C170.0122 (8)0.0181 (9)0.0179 (9)0.0023 (7)0.0043 (7)0.0044 (7)
C180.0159 (9)0.0136 (8)0.0150 (8)0.0022 (7)0.0087 (7)0.0022 (7)
O30.0179 (7)0.0206 (7)0.0178 (6)0.0036 (5)0.0104 (5)0.0033 (5)
O40.0181 (6)0.0189 (7)0.0227 (7)0.0026 (5)0.0142 (6)0.0041 (5)
C190.0222 (9)0.0163 (9)0.0205 (9)0.0009 (7)0.0157 (8)0.0009 (7)
C200.0295 (11)0.0186 (10)0.0253 (10)0.0027 (8)0.0181 (9)0.0027 (8)
B10.0122 (9)0.0110 (9)0.0111 (8)0.0009 (7)0.0061 (7)0.0004 (7)
C210.0091 (8)0.0154 (8)0.0124 (8)0.0028 (6)0.0046 (7)0.0006 (6)
C220.0146 (9)0.0169 (9)0.0153 (8)0.0017 (7)0.0068 (7)0.0005 (7)
C230.0186 (9)0.0206 (9)0.0196 (9)0.0018 (7)0.0099 (8)0.0042 (7)
C240.0164 (9)0.0268 (10)0.0111 (8)0.0058 (7)0.0080 (7)0.0035 (7)
C250.0168 (9)0.0213 (9)0.0113 (8)0.0027 (7)0.0039 (7)0.0031 (7)
C260.0155 (9)0.0123 (8)0.0154 (8)0.0002 (7)0.0072 (7)0.0006 (7)
C270.0142 (8)0.0081 (8)0.0124 (8)0.0022 (6)0.0052 (7)0.0007 (6)
C280.0156 (9)0.0146 (8)0.0135 (8)0.0005 (7)0.0068 (7)0.0008 (6)
C290.0119 (8)0.0159 (9)0.0208 (9)0.0005 (7)0.0063 (7)0.0005 (7)
C300.0150 (9)0.0117 (8)0.0148 (8)0.0026 (7)0.0016 (7)0.0003 (6)
C310.0241 (10)0.0131 (8)0.0116 (8)0.0043 (7)0.0070 (7)0.0012 (6)
C320.0155 (8)0.0133 (8)0.0163 (8)0.0013 (7)0.0081 (7)0.0006 (7)
C330.0140 (8)0.0124 (8)0.0105 (7)0.0006 (6)0.0079 (7)0.0020 (6)
C340.0151 (8)0.0149 (8)0.0122 (8)0.0018 (7)0.0067 (7)0.0015 (6)
C350.0123 (8)0.0248 (10)0.0142 (8)0.0006 (7)0.0070 (7)0.0028 (7)
C360.0189 (9)0.0195 (9)0.0206 (9)0.0096 (7)0.0121 (8)0.0072 (7)
C370.0272 (10)0.0112 (9)0.0202 (9)0.0034 (7)0.0109 (8)0.0007 (7)
C380.0135 (8)0.0150 (9)0.0161 (8)0.0008 (7)0.0054 (7)0.0014 (7)
C390.0150 (8)0.0135 (8)0.0078 (7)0.0005 (7)0.0045 (7)0.0004 (6)
C400.0179 (9)0.0182 (9)0.0151 (8)0.0019 (7)0.0086 (7)0.0002 (7)
C410.0260 (10)0.0153 (9)0.0141 (8)0.0078 (7)0.0068 (8)0.0013 (7)
C420.0344 (11)0.0129 (9)0.0138 (8)0.0025 (8)0.0080 (8)0.0012 (7)
C430.0255 (10)0.0172 (9)0.0179 (9)0.0056 (8)0.0124 (8)0.0008 (7)
C440.0202 (9)0.0140 (8)0.0155 (8)0.0003 (7)0.0098 (7)0.0015 (7)
B20.0113 (9)0.0102 (9)0.0098 (8)0.0013 (7)0.0055 (7)0.0015 (7)
C450.0134 (8)0.0090 (8)0.0130 (8)0.0008 (6)0.0042 (7)0.0030 (6)
C460.0160 (9)0.0118 (8)0.0208 (9)0.0004 (7)0.0067 (8)0.0028 (7)
C470.0126 (9)0.0141 (9)0.0281 (10)0.0017 (7)0.0012 (8)0.0037 (8)
C480.0239 (10)0.0123 (9)0.0179 (9)0.0014 (7)0.0045 (8)0.0032 (7)
C490.0310 (11)0.0184 (10)0.0122 (8)0.0024 (8)0.0059 (8)0.0010 (7)
C500.0181 (9)0.0166 (9)0.0155 (8)0.0016 (7)0.0066 (7)0.0011 (7)
C510.0107 (8)0.0134 (8)0.0066 (7)0.0004 (6)0.0006 (6)0.0006 (6)
C520.0136 (8)0.0160 (9)0.0136 (8)0.0026 (7)0.0038 (7)0.0005 (7)
C530.0209 (10)0.0141 (9)0.0166 (9)0.0030 (7)0.0022 (8)0.0031 (7)
C540.0232 (10)0.0122 (9)0.0192 (9)0.0028 (7)0.0015 (8)0.0007 (7)
C550.0180 (9)0.0203 (10)0.0190 (9)0.0067 (8)0.0029 (8)0.0052 (7)
C560.0172 (9)0.0176 (9)0.0139 (8)0.0017 (7)0.0065 (7)0.0020 (7)
C570.0139 (8)0.0123 (8)0.0109 (7)0.0000 (6)0.0082 (7)0.0022 (6)
C580.0163 (9)0.0152 (8)0.0122 (8)0.0003 (7)0.0087 (7)0.0027 (6)
C590.0156 (9)0.0239 (10)0.0161 (8)0.0062 (7)0.0096 (7)0.0098 (7)
C600.0273 (10)0.0191 (9)0.0203 (9)0.0106 (8)0.0186 (8)0.0086 (7)
C610.0293 (10)0.0138 (9)0.0152 (8)0.0018 (7)0.0145 (8)0.0003 (7)
C620.0166 (9)0.0160 (9)0.0130 (8)0.0004 (7)0.0073 (7)0.0011 (7)
C630.0105 (8)0.0113 (8)0.0151 (8)0.0030 (6)0.0075 (7)0.0000 (6)
C640.0148 (9)0.0157 (9)0.0180 (9)0.0001 (7)0.0086 (7)0.0022 (7)
C650.0167 (9)0.0156 (9)0.0303 (10)0.0014 (7)0.0159 (8)0.0002 (8)
C660.0233 (10)0.0187 (9)0.0267 (10)0.0068 (8)0.0196 (8)0.0064 (8)
C670.0186 (9)0.0236 (10)0.0151 (8)0.0047 (7)0.0086 (8)0.0022 (7)
C680.0132 (8)0.0176 (9)0.0154 (8)0.0008 (7)0.0069 (7)0.0005 (7)
Geometric parameters (Å, º) top
N1—C11.323 (2)C25—H250.9500
N1—C31.460 (2)C26—H260.9500
N1—C21.465 (2)C27—C281.400 (2)
N2—C11.333 (2)C27—C321.404 (2)
N2—C41.464 (2)C28—C291.398 (2)
N2—C51.477 (2)C28—H280.9500
N3—C11.379 (2)C29—C301.382 (3)
N3—C81.406 (2)C29—H290.9500
N3—C71.495 (2)C30—C311.391 (3)
C2—H2A0.9800C30—H300.9500
C2—H2B0.9800C31—C321.388 (2)
C2—H2C0.9800C31—H310.9500
C3—H3A0.9800C32—H320.9500
C3—H3B0.9800C33—C381.400 (2)
C3—H3C0.9800C33—C341.408 (2)
C4—H4A0.9800C34—C351.387 (3)
C4—H4B0.9800C34—H340.9500
C4—H4C0.9800C35—C361.391 (3)
C5—C61.511 (3)C35—H350.9500
C5—H5A0.9900C36—C371.381 (3)
C5—H5B0.9900C36—H360.9500
C6—C71.521 (3)C37—C381.391 (3)
C6—H6A0.9900C37—H370.9500
C6—H6B0.9900C38—H380.9500
C7—H7A0.9900C39—C441.400 (2)
C7—H7B0.9900C39—C401.411 (2)
C8—O11.199 (2)C40—C411.386 (3)
C8—O21.331 (2)C40—H400.9500
O2—C91.465 (2)C41—C421.386 (3)
C9—C101.499 (3)C41—H410.9500
C9—H9A0.9900C42—C431.380 (3)
C9—H9B0.9900C42—H420.9500
C10—H10A0.9800C43—C441.405 (3)
C10—H10B0.9800C43—H430.9500
C10—H10C0.9800C44—H440.9500
N4—C111.326 (2)B2—C511.638 (2)
N4—C121.464 (2)B2—C631.643 (2)
N4—C131.472 (2)B2—C451.643 (2)
N5—C111.324 (2)B2—C571.645 (2)
N5—C141.463 (2)C45—C461.405 (2)
N5—C151.474 (2)C45—C501.405 (2)
N6—C111.381 (2)C46—C471.391 (3)
N6—C181.409 (2)C46—H460.9500
N6—C171.482 (2)C47—C481.384 (3)
C12—H12A0.9800C47—H470.9500
C12—H12B0.9800C48—C491.383 (3)
C12—H12C0.9800C48—H480.9500
C13—H13A0.9800C49—C501.392 (3)
C13—H13B0.9800C49—H490.9500
C13—H13C0.9800C50—H500.9500
C14—H14A0.9800C51—C521.404 (2)
C14—H14B0.9800C51—C561.407 (2)
C14—H14C0.9800C52—C531.392 (3)
C15—C161.506 (3)C52—H520.9500
C15—H15A0.9900C53—C541.386 (3)
C15—H15B0.9900C53—H530.9500
C16—C171.501 (3)C54—C551.380 (3)
C16—H16A0.9900C54—H540.9500
C16—H16B0.9900C55—C561.397 (3)
C17—H17A0.9900C55—H550.9500
C17—H17B0.9900C56—H560.9500
C18—O31.202 (2)C57—C621.400 (2)
C18—O41.329 (2)C57—C581.405 (2)
O4—C191.456 (2)C58—C591.402 (3)
C19—C201.504 (3)C58—H580.9500
C19—H19A0.9900C59—C601.386 (3)
C19—H19B0.9900C59—H590.9500
C20—H20A0.9800C60—C611.386 (3)
C20—H20B0.9800C60—H600.9500
C20—H20C0.9800C61—C621.393 (3)
B1—C271.640 (2)C61—H610.9500
B1—C331.640 (2)C62—H620.9500
B1—C211.644 (2)C63—C641.401 (2)
B1—C391.645 (3)C63—C681.404 (2)
C21—C261.399 (2)C64—C651.396 (3)
C21—C221.408 (2)C64—H640.9500
C22—C231.387 (3)C65—C661.377 (3)
C22—H220.9500C65—H650.9500
C23—C241.384 (3)C66—C671.389 (3)
C23—H230.9500C66—H660.9500
C24—C251.385 (3)C67—C681.383 (3)
C24—H240.9500C67—H670.9500
C25—C261.390 (2)C68—H680.9500
C1—N1—C3123.43 (15)C22—C23—H23120.0
C1—N1—C2122.60 (15)C23—C24—C25119.17 (16)
C3—N1—C2113.85 (15)C23—C24—H24120.4
C1—N2—C4122.45 (15)C25—C24—H24120.4
C1—N2—C5115.92 (14)C24—C25—C26120.10 (17)
C4—N2—C5117.00 (15)C24—C25—H25119.9
C1—N3—C8120.35 (14)C26—C25—H25119.9
C1—N3—C7120.94 (14)C25—C26—C21122.79 (17)
C8—N3—C7118.37 (14)C25—C26—H26118.6
N1—C1—N2122.69 (16)C21—C26—H26118.6
N1—C1—N3120.46 (15)C28—C27—C32115.13 (15)
N2—C1—N3116.84 (15)C28—C27—B1126.56 (15)
N1—C2—H2A109.5C32—C27—B1118.29 (15)
N1—C2—H2B109.5C29—C28—C27122.91 (16)
H2A—C2—H2B109.5C29—C28—H28118.5
N1—C2—H2C109.5C27—C28—H28118.5
H2A—C2—H2C109.5C30—C29—C28119.99 (17)
H2B—C2—H2C109.5C30—C29—H29120.0
N1—C3—H3A109.5C28—C29—H29120.0
N1—C3—H3B109.5C29—C30—C31118.90 (16)
H3A—C3—H3B109.5C29—C30—H30120.5
N1—C3—H3C109.5C31—C30—H30120.5
H3A—C3—H3C109.5C32—C31—C30120.24 (16)
H3B—C3—H3C109.5C32—C31—H31119.9
N2—C4—H4A109.5C30—C31—H31119.9
N2—C4—H4B109.5C31—C32—C27122.83 (17)
H4A—C4—H4B109.5C31—C32—H32118.6
N2—C4—H4C109.5C27—C32—H32118.6
H4A—C4—H4C109.5C38—C33—C34115.37 (15)
H4B—C4—H4C109.5C38—C33—B1124.00 (15)
N2—C5—C6106.66 (15)C34—C33—B1120.32 (15)
N2—C5—H5A110.4C35—C34—C33122.77 (16)
C6—C5—H5A110.4C35—C34—H34118.6
N2—C5—H5B110.4C33—C34—H34118.6
C6—C5—H5B110.4C34—C35—C36120.13 (17)
H5A—C5—H5B108.6C34—C35—H35119.9
C5—C6—C7108.33 (15)C36—C35—H35119.9
C5—C6—H6A110.0C37—C36—C35118.53 (17)
C7—C6—H6A110.0C37—C36—H36120.7
C5—C6—H6B110.0C35—C36—H36120.7
C7—C6—H6B110.0C36—C37—C38120.91 (17)
H6A—C6—H6B108.4C36—C37—H37119.5
N3—C7—C6111.26 (15)C38—C37—H37119.5
N3—C7—H7A109.4C37—C38—C33122.27 (17)
C6—C7—H7A109.4C37—C38—H38118.9
N3—C7—H7B109.4C33—C38—H38118.9
C6—C7—H7B109.4C44—C39—C40115.27 (16)
H7A—C7—H7B108.0C44—C39—B1125.15 (15)
O1—C8—O2126.89 (16)C40—C39—B1119.51 (15)
O1—C8—N3124.10 (16)C41—C40—C39122.80 (17)
O2—C8—N3109.02 (14)C41—C40—H40118.6
C8—O2—C9115.89 (14)C39—C40—H40118.6
O2—C9—C10110.73 (15)C42—C41—C40120.11 (18)
O2—C9—H9A109.5C42—C41—H41119.9
C10—C9—H9A109.5C40—C41—H41119.9
O2—C9—H9B109.5C43—C42—C41119.36 (18)
C10—C9—H9B109.5C43—C42—H42120.3
H9A—C9—H9B108.1C41—C42—H42120.3
C9—C10—H10A109.5C42—C43—C44119.98 (18)
C9—C10—H10B109.5C42—C43—H43120.0
H10A—C10—H10B109.5C44—C43—H43120.0
C9—C10—H10C109.5C39—C44—C43122.44 (17)
H10A—C10—H10C109.5C39—C44—H44118.8
H10B—C10—H10C109.5C43—C44—H44118.8
C11—N4—C12121.76 (15)C51—B2—C63110.53 (13)
C11—N4—C13122.96 (14)C51—B2—C45104.41 (13)
C12—N4—C13114.62 (14)C63—B2—C45113.29 (14)
C11—N5—C14121.88 (16)C51—B2—C57114.51 (14)
C11—N5—C15123.72 (16)C63—B2—C57102.97 (13)
C14—N5—C15114.09 (15)C45—B2—C57111.43 (13)
C11—N6—C18118.74 (14)C46—C45—C50115.44 (16)
C11—N6—C17116.00 (14)C46—C45—B2123.48 (15)
C18—N6—C17118.83 (14)C50—C45—B2120.84 (15)
N5—C11—N4122.18 (16)C47—C46—C45122.56 (18)
N5—C11—N6117.57 (15)C47—C46—H46118.7
N4—C11—N6120.11 (15)C45—C46—H46118.7
N4—C12—H12A109.5C48—C47—C46120.02 (18)
N4—C12—H12B109.5C48—C47—H47120.0
H12A—C12—H12B109.5C46—C47—H47120.0
N4—C12—H12C109.5C49—C48—C47119.43 (17)
H12A—C12—H12C109.5C49—C48—H48120.3
H12B—C12—H12C109.5C47—C48—H48120.3
N4—C13—H13A109.5C48—C49—C50119.97 (18)
N4—C13—H13B109.5C48—C49—H49120.0
H13A—C13—H13B109.5C50—C49—H49120.0
N4—C13—H13C109.5C49—C50—C45122.54 (18)
H13A—C13—H13C109.5C49—C50—H50118.7
H13B—C13—H13C109.5C45—C50—H50118.7
N5—C14—H14A109.5C52—C51—C56115.31 (16)
N5—C14—H14B109.5C52—C51—B2120.42 (15)
H14A—C14—H14B109.5C56—C51—B2124.02 (15)
N5—C14—H14C109.5C53—C52—C51122.68 (17)
H14A—C14—H14C109.5C53—C52—H52118.7
H14B—C14—H14C109.5C51—C52—H52118.7
N5—C15—C16113.56 (16)C54—C53—C52120.12 (18)
N5—C15—H15A108.9C54—C53—H53119.9
C16—C15—H15A108.9C52—C53—H53119.9
N5—C15—H15B108.9C55—C54—C53119.23 (17)
C16—C15—H15B108.9C55—C54—H54120.4
H15A—C15—H15B107.7C53—C54—H54120.4
C17—C16—C15108.01 (17)C54—C55—C56120.19 (18)
C17—C16—H16A110.1C54—C55—H55119.9
C15—C16—H16A110.1C56—C55—H55119.9
C17—C16—H16B110.1C55—C56—C51122.46 (18)
C15—C16—H16B110.1C55—C56—H56118.8
H16A—C16—H16B108.4C51—C56—H56118.8
N6—C17—C16105.98 (15)C62—C57—C58115.31 (16)
N6—C17—H17A110.5C62—C57—B2120.82 (15)
C16—C17—H17A110.5C58—C57—B2123.41 (15)
N6—C17—H17B110.5C59—C58—C57122.58 (17)
C16—C17—H17B110.5C59—C58—H58118.7
H17A—C17—H17B108.7C57—C58—H58118.7
O3—C18—O4126.37 (16)C60—C59—C58119.97 (17)
O3—C18—N6124.48 (16)C60—C59—H59120.0
O4—C18—N6109.15 (15)C58—C59—H59120.0
C18—O4—C19115.60 (14)C59—C60—C61119.07 (17)
O4—C19—C20110.62 (15)C59—C60—H60120.5
O4—C19—H19A109.5C61—C60—H60120.5
C20—C19—H19A109.5C60—C61—C62120.19 (17)
O4—C19—H19B109.5C60—C61—H61119.9
C20—C19—H19B109.5C62—C61—H61119.9
H19A—C19—H19B108.1C61—C62—C57122.88 (17)
C19—C20—H20A109.5C61—C62—H62118.6
C19—C20—H20B109.5C57—C62—H62118.6
H20A—C20—H20B109.5C64—C63—C68114.99 (16)
C19—C20—H20C109.5C64—C63—B2123.41 (15)
H20A—C20—H20C109.5C68—C63—B2121.14 (15)
H20B—C20—H20C109.5C65—C64—C63122.94 (17)
C27—B1—C33110.48 (14)C65—C64—H64118.5
C27—B1—C21114.04 (14)C63—C64—H64118.5
C33—B1—C21102.80 (13)C66—C65—C64119.99 (17)
C27—B1—C39106.22 (13)C66—C65—H65120.0
C33—B1—C39113.27 (14)C64—C65—H65120.0
C21—B1—C39110.23 (14)C65—C66—C67118.89 (17)
C26—C21—C22115.13 (15)C65—C66—H66120.6
C26—C21—B1122.76 (15)C67—C66—H66120.6
C22—C21—B1121.83 (15)C68—C67—C66120.45 (17)
C23—C22—C21122.84 (17)C68—C67—H67119.8
C23—C22—H22118.6C66—C67—H67119.8
C21—C22—H22118.6C67—C68—C63122.73 (17)
C24—C23—C22119.94 (17)C67—C68—H68118.6
C24—C23—H23120.0C63—C68—H68118.6
C3—N1—C1—N2157.48 (16)C27—B1—C33—C34168.69 (15)
C2—N1—C1—N226.7 (2)C21—B1—C33—C3469.26 (18)
C3—N1—C1—N321.4 (2)C39—B1—C33—C3449.7 (2)
C2—N1—C1—N3154.40 (15)C38—C33—C34—C351.0 (2)
C4—N2—C1—N133.4 (3)B1—C33—C34—C35174.89 (16)
C5—N2—C1—N1171.44 (16)C33—C34—C35—C361.0 (3)
C4—N2—C1—N3145.49 (17)C34—C35—C36—C370.1 (3)
C5—N2—C1—N39.6 (2)C35—C36—C37—C381.2 (3)
C8—N3—C1—N141.4 (2)C36—C37—C38—C331.1 (3)
C7—N3—C1—N1145.28 (16)C34—C33—C38—C370.1 (2)
C8—N3—C1—N2139.61 (16)B1—C33—C38—C37173.56 (16)
C7—N3—C1—N233.7 (2)C27—B1—C39—C44110.49 (18)
C1—N2—C5—C658.4 (2)C33—B1—C39—C4411.0 (2)
C4—N2—C5—C698.17 (18)C21—B1—C39—C44125.50 (17)
N2—C5—C6—C763.43 (19)C27—B1—C39—C4066.51 (18)
C1—N3—C7—C623.6 (2)C33—B1—C39—C40172.05 (14)
C8—N3—C7—C6149.82 (16)C21—B1—C39—C4057.5 (2)
C5—C6—C7—N325.2 (2)C44—C39—C40—C412.2 (2)
C1—N3—C8—O116.0 (3)B1—C39—C40—C41179.49 (16)
C7—N3—C8—O1157.45 (17)C39—C40—C41—C421.1 (3)
C1—N3—C8—O2164.46 (15)C40—C41—C42—C430.4 (3)
C7—N3—C8—O222.1 (2)C41—C42—C43—C440.8 (3)
O1—C8—O2—C93.0 (3)C40—C39—C44—C431.8 (2)
N3—C8—O2—C9176.55 (14)B1—C39—C44—C43178.92 (16)
C8—O2—C9—C1084.87 (19)C42—C43—C44—C390.4 (3)
C14—N5—C11—N419.6 (3)C51—B2—C45—C4688.03 (19)
C15—N5—C11—N4167.15 (17)C63—B2—C45—C4632.3 (2)
C14—N5—C11—N6155.88 (17)C57—B2—C45—C46147.84 (16)
C15—N5—C11—N617.3 (3)C51—B2—C45—C5086.17 (18)
C12—N4—C11—N5152.35 (17)C63—B2—C45—C50153.51 (16)
C13—N4—C11—N537.4 (3)C57—B2—C45—C5038.0 (2)
C12—N4—C11—N623.1 (2)C50—C45—C46—C471.3 (3)
C13—N4—C11—N6147.19 (16)B2—C45—C46—C47175.75 (16)
C18—N6—C11—N5133.56 (17)C45—C46—C47—C480.4 (3)
C17—N6—C11—N518.0 (2)C46—C47—C48—C490.7 (3)
C18—N6—C11—N450.8 (2)C47—C48—C49—C501.0 (3)
C17—N6—C11—N4157.63 (16)C48—C49—C50—C450.1 (3)
C11—N5—C15—C168.6 (3)C46—C45—C50—C491.0 (3)
C14—N5—C15—C16165.11 (18)B2—C45—C50—C49175.67 (17)
N5—C15—C16—C1732.7 (2)C63—B2—C51—C5239.9 (2)
C11—N6—C17—C1658.6 (2)C45—B2—C51—C5282.29 (18)
C18—N6—C17—C1692.93 (19)C57—B2—C51—C52155.59 (15)
C15—C16—C17—N663.05 (19)C63—B2—C51—C56146.22 (16)
C11—N6—C18—O33.9 (3)C45—B2—C51—C5691.62 (18)
C17—N6—C18—O3154.68 (17)C57—B2—C51—C5630.5 (2)
C11—N6—C18—O4176.03 (15)C56—C51—C52—C530.6 (2)
C17—N6—C18—O425.3 (2)B2—C51—C52—C53175.06 (15)
O3—C18—O4—C197.9 (3)C51—C52—C53—C540.0 (3)
N6—C18—O4—C19172.08 (14)C52—C53—C54—C551.0 (3)
C18—O4—C19—C2080.33 (19)C53—C54—C55—C561.2 (3)
C27—B1—C21—C26137.68 (16)C54—C55—C56—C510.5 (3)
C33—B1—C21—C26102.71 (18)C52—C51—C56—C550.4 (2)
C39—B1—C21—C2618.3 (2)B2—C51—C56—C55174.60 (16)
C27—B1—C21—C2248.7 (2)C51—B2—C57—C62154.21 (15)
C33—B1—C21—C2270.94 (19)C63—B2—C57—C6285.76 (17)
C39—B1—C21—C22168.04 (15)C45—B2—C57—C6236.0 (2)
C26—C21—C22—C232.1 (3)C51—B2—C57—C5833.9 (2)
B1—C21—C22—C23176.23 (16)C63—B2—C57—C5886.11 (18)
C21—C22—C23—C241.5 (3)C45—B2—C57—C58152.13 (15)
C22—C23—C24—C250.4 (3)C62—C57—C58—C590.4 (2)
C23—C24—C25—C261.4 (3)B2—C57—C58—C59172.67 (15)
C24—C25—C26—C210.6 (3)C57—C58—C59—C600.0 (3)
C22—C21—C26—C251.1 (3)C58—C59—C60—C610.3 (3)
B1—C21—C26—C25175.13 (16)C59—C60—C61—C620.3 (3)
C33—B1—C27—C28121.25 (18)C60—C61—C62—C570.1 (3)
C21—B1—C27—C286.1 (2)C58—C57—C62—C610.4 (2)
C39—B1—C27—C28115.53 (18)B2—C57—C62—C61172.91 (16)
C33—B1—C27—C3260.7 (2)C51—B2—C63—C64152.35 (16)
C21—B1—C27—C32175.83 (15)C45—B2—C63—C6435.6 (2)
C39—B1—C27—C3262.57 (19)C57—B2—C63—C6484.91 (19)
C32—C27—C28—C290.3 (3)C51—B2—C63—C6835.8 (2)
B1—C27—C28—C29178.48 (16)C45—B2—C63—C68152.59 (15)
C27—C28—C29—C300.1 (3)C57—B2—C63—C6886.92 (18)
C28—C29—C30—C310.4 (3)C68—C63—C64—C650.4 (3)
C29—C30—C31—C320.5 (3)B2—C63—C64—C65171.90 (16)
C30—C31—C32—C270.2 (3)C63—C64—C65—C660.9 (3)
C28—C27—C32—C310.2 (3)C64—C65—C66—C670.7 (3)
B1—C27—C32—C31178.48 (16)C65—C66—C67—C680.0 (3)
C27—B1—C33—C3818.0 (2)C66—C67—C68—C630.5 (3)
C21—B1—C33—C38104.06 (18)C64—C63—C68—C670.3 (3)
C39—B1—C33—C38137.01 (16)B2—C63—C68—C67172.78 (16)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C21–C26, C27–C32, C45–C50, C51–C56, C57–C62 and C63–C68 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5A···Cg10.992.773.502 (3)131
C19—H19B···Cg10.992.863.559 (3)128
C17—H17B···Cg20.992.673.632 (3)165
C6—H6B···Cg30.992.753.624 (3)147
C13—H13C···Cg30.982.723.421 (3)129
C13—H13B···Cg40.982.673.583 (3)154
C12—H12C···Cg50.982.703.329 (3)121
C14—H14B···Cg50.982.763.354 (3)120
C12—H12B···Cg60.982.643.535 (3)151
C9—H9A···Cg60.992.753.655 (3)151
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C21–C26, C27–C32, C45–C50, C51–C56, C57–C62 and C63–C68 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5A···Cg10.992.773.502 (3)131
C19—H19B···Cg10.992.863.559 (3)128
C17—H17B···Cg20.992.673.632 (3)165
C6—H6B···Cg30.992.753.624 (3)147
C13—H13C···Cg30.982.723.421 (3)129
C13—H13B···Cg40.982.673.583 (3)154
C12—H12C···Cg50.982.703.329 (3)121
C14—H14B···Cg50.982.763.354 (3)120
C12—H12B···Cg60.982.643.535 (3)151
C9—H9A···Cg60.992.753.655 (3)151
 

Acknowledgements

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

References

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