organic compounds
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
The 10H20N3O2+·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.
of the title salt, CCCDC reference: 1432704
1. Related literature
For the crystal structures of alkali metal tetraphenylborates, see: Behrens et al. (2012). For the of 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate, see: Tiritiris & Kantlehner (2012a). For the of 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide, see: Tiritiris & Kantlehner, 2012b.
2. Experimental
2.1. Crystal data
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2.2. Data collection
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2.3. Refinement
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Data collection: COLLECT (Hooft, 2004); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; 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.
Supporting information
CCDC reference: 1432704
https://doi.org/10.1107/S2056989015020034/zl2648sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020034/zl2648Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015020034/zl2648Isup3.cml
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%).
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).
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 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.
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 analysis of the alkali metal tetraphenylborates (Behrens et al., 2012). C–H···For the crystal structures of alkali metal tetraphenylborates, see: Behrens et al. (2012). For the
of 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate, see: Tiritiris & Kantlehner (2012a). For the of 1-benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide, see: Tiritiris & Kantlehner, 2012b.Data collection: COLLECT (Hooft, 2004); cell
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).C10H20N3O2+·C24H20B− | F(000) = 2288 |
Mr = 533.50 | Dx = 1.223 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 26101 reflections |
a = 18.5710 (5) Å | θ = 1.3–28.1° |
b = 19.2164 (7) Å | µ = 0.08 mm−1 |
c = 18.6107 (5) Å | T = 100 K |
β = 119.280 (2)° | Block, colorless |
V = 5793.0 (3) Å3 | 0.24 × 0.17 × 0.12 mm |
Z = 8 |
Bruker–Nonius KappaCCD diffractometer | 9686 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 28.2°, θmin = 1.3° |
φ scans, and ω scans | h = −24→24 |
26283 measured reflections | k = −25→23 |
14001 independent reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-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 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C10H20N3O2+·C24H20B− | V = 5793.0 (3) Å3 |
Mr = 533.50 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.5710 (5) Å | µ = 0.08 mm−1 |
b = 19.2164 (7) Å | T = 100 K |
c = 18.6107 (5) Å | 0.24 × 0.17 × 0.12 mm |
β = 119.280 (2)° |
Bruker–Nonius KappaCCD diffractometer | 9686 reflections with I > 2σ(I) |
26283 measured reflections | Rint = 0.058 |
14001 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.50 e Å−3 |
14001 reflections | Δρmin = −0.25 e Å−3 |
729 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.79842 (9) | 0.55416 (8) | −0.00502 (9) | 0.0141 (3) | |
N2 | 0.81433 (9) | 0.67471 (8) | 0.00009 (9) | 0.0157 (3) | |
N3 | 0.72182 (9) | 0.62582 (8) | 0.03487 (9) | 0.0135 (3) | |
C1 | 0.77986 (10) | 0.61714 (9) | 0.00972 (10) | 0.0129 (3) | |
C2 | 0.87832 (12) | 0.53755 (11) | 0.00129 (11) | 0.0204 (4) | |
H2A | 0.8711 | 0.5301 | −0.0540 | 0.031* | |
H2B | 0.9006 | 0.4952 | 0.0342 | 0.031* | |
H2C | 0.9167 | 0.5762 | 0.0279 | 0.031* | |
C3 | 0.74394 (12) | 0.49416 (9) | −0.02357 (12) | 0.0195 (4) | |
H3A | 0.7667 | 0.4625 | 0.0238 | 0.029* | |
H3B | 0.7395 | 0.4697 | −0.0718 | 0.029* | |
H3C | 0.6891 | 0.5099 | −0.0351 | 0.029* | |
C4 | 0.83819 (13) | 0.68127 (11) | −0.06387 (12) | 0.0214 (4) | |
H4A | 0.8189 | 0.6404 | −0.0999 | 0.032* | |
H4B | 0.8984 | 0.6845 | −0.0380 | 0.032* | |
H4C | 0.8132 | 0.7233 | −0.0964 | 0.032* | |
C5 | 0.79627 (12) | 0.73980 (10) | 0.03049 (12) | 0.0207 (4) | |
H5A | 0.8229 | 0.7799 | 0.0193 | 0.025* | |
H5B | 0.8172 | 0.7369 | 0.0906 | 0.025* | |
C6 | 0.70353 (12) | 0.74823 (10) | −0.01491 (12) | 0.0216 (4) | |
H6A | 0.6826 | 0.7484 | −0.0751 | 0.026* | |
H6B | 0.6881 | 0.7929 | 0.0005 | 0.026* | |
C7 | 0.66602 (11) | 0.68779 (9) | 0.00827 (11) | 0.0156 (4) | |
H7A | 0.6558 | 0.7023 | 0.0536 | 0.019* | |
H7B | 0.6123 | 0.6751 | −0.0397 | 0.019* | |
C8 | 0.71983 (11) | 0.58034 (9) | 0.09302 (11) | 0.0142 (3) | |
O1 | 0.77527 (8) | 0.54207 (7) | 0.13625 (8) | 0.0191 (3) | |
O2 | 0.64801 (8) | 0.58761 (7) | 0.09186 (8) | 0.0184 (3) | |
C9 | 0.63793 (12) | 0.54654 (10) | 0.15269 (12) | 0.0190 (4) | |
H9A | 0.5975 | 0.5697 | 0.1650 | 0.023* | |
H9B | 0.6913 | 0.5439 | 0.2045 | 0.023* | |
C10 | 0.60852 (13) | 0.47449 (11) | 0.12107 (13) | 0.0257 (4) | |
H10A | 0.5553 | 0.4771 | 0.0702 | 0.039* | |
H10B | 0.6020 | 0.4479 | 0.1625 | 0.039* | |
H10C | 0.6490 | 0.4513 | 0.1098 | 0.039* | |
N4 | 0.63551 (9) | 0.36665 (8) | 0.40962 (9) | 0.0135 (3) | |
N5 | 0.73941 (10) | 0.38338 (8) | 0.54432 (9) | 0.0182 (3) | |
N6 | 0.77452 (9) | 0.36757 (8) | 0.44206 (9) | 0.0150 (3) | |
C11 | 0.71453 (11) | 0.37415 (9) | 0.46510 (10) | 0.0124 (3) | |
C12 | 0.60942 (11) | 0.32737 (10) | 0.33341 (11) | 0.0170 (4) | |
H12A | 0.5936 | 0.3598 | 0.2875 | 0.025* | |
H12B | 0.5621 | 0.2980 | 0.3227 | 0.025* | |
H12C | 0.6551 | 0.2980 | 0.3391 | 0.025* | |
C13 | 0.56893 (11) | 0.40535 (10) | 0.41317 (11) | 0.0167 (4) | |
H13A | 0.5341 | 0.3729 | 0.4232 | 0.025* | |
H13B | 0.5354 | 0.4294 | 0.3607 | 0.025* | |
H13C | 0.5930 | 0.4395 | 0.4579 | 0.025* | |
C14 | 0.68755 (14) | 0.36456 (12) | 0.58036 (12) | 0.0276 (5) | |
H14A | 0.6620 | 0.4066 | 0.5878 | 0.041* | |
H14B | 0.7215 | 0.3422 | 0.6339 | 0.041* | |
H14C | 0.6444 | 0.3322 | 0.5436 | 0.041* | |
C15 | 0.82339 (12) | 0.40587 (12) | 0.60501 (12) | 0.0268 (5) | |
H15A | 0.8453 | 0.3740 | 0.6529 | 0.032* | |
H15B | 0.8204 | 0.4530 | 0.6248 | 0.032* | |
C16 | 0.88247 (13) | 0.40729 (11) | 0.57137 (13) | 0.0273 (5) | |
H16A | 0.8796 | 0.4529 | 0.5453 | 0.033* | |
H16B | 0.9397 | 0.4002 | 0.6164 | 0.033* | |
C17 | 0.85854 (11) | 0.35009 (10) | 0.50887 (11) | 0.0174 (4) | |
H17A | 0.8977 | 0.3477 | 0.4872 | 0.021* | |
H17B | 0.8584 | 0.3046 | 0.5338 | 0.021* | |
C18 | 0.76607 (11) | 0.40591 (9) | 0.37379 (10) | 0.0144 (3) | |
O3 | 0.70768 (8) | 0.44185 (7) | 0.33087 (7) | 0.0180 (3) | |
O4 | 0.83231 (8) | 0.39572 (7) | 0.36536 (8) | 0.0181 (3) | |
C19 | 0.83792 (12) | 0.43919 (10) | 0.30418 (11) | 0.0174 (4) | |
H19A | 0.7827 | 0.4434 | 0.2549 | 0.021* | |
H19B | 0.8754 | 0.4171 | 0.2872 | 0.021* | |
C20 | 0.86987 (13) | 0.51034 (10) | 0.33867 (12) | 0.0224 (4) | |
H20A | 0.8303 | 0.5338 | 0.3509 | 0.034* | |
H20B | 0.8771 | 0.5377 | 0.2982 | 0.034* | |
H20C | 0.9230 | 0.5059 | 0.3893 | 0.034* | |
B1 | 0.98280 (12) | 0.63490 (10) | 0.78042 (11) | 0.0113 (4) | |
C21 | 0.98217 (10) | 0.64626 (9) | 0.69255 (10) | 0.0125 (3) | |
C22 | 1.01083 (11) | 0.70816 (10) | 0.67468 (11) | 0.0158 (4) | |
H22 | 1.0341 | 0.7430 | 0.7161 | 0.019* | |
C23 | 1.00657 (11) | 0.72050 (10) | 0.59924 (11) | 0.0193 (4) | |
H23 | 1.0278 | 0.7626 | 0.5903 | 0.023* | |
C24 | 0.97130 (11) | 0.67145 (10) | 0.53708 (10) | 0.0176 (4) | |
H24 | 0.9684 | 0.6794 | 0.4854 | 0.021* | |
C25 | 0.94022 (11) | 0.61059 (10) | 0.55120 (11) | 0.0178 (4) | |
H25 | 0.9148 | 0.5770 | 0.5086 | 0.021* | |
C26 | 0.94618 (11) | 0.59863 (9) | 0.62756 (10) | 0.0145 (3) | |
H26 | 0.9249 | 0.5563 | 0.6360 | 0.017* | |
C27 | 1.07086 (10) | 0.65452 (9) | 0.86183 (10) | 0.0122 (3) | |
C28 | 1.14423 (11) | 0.67309 (9) | 0.86286 (10) | 0.0147 (3) | |
H28 | 1.1443 | 0.6760 | 0.8119 | 0.018* | |
C29 | 1.21742 (11) | 0.68755 (9) | 0.93552 (11) | 0.0169 (4) | |
H29 | 1.2658 | 0.7000 | 0.9333 | 0.020* | |
C30 | 1.21940 (11) | 0.68370 (9) | 1.01061 (11) | 0.0163 (4) | |
H30 | 1.2688 | 0.6937 | 1.0603 | 0.020* | |
C31 | 1.14793 (11) | 0.66496 (9) | 1.01231 (11) | 0.0170 (4) | |
H31 | 1.1484 | 0.6617 | 1.0635 | 0.020* | |
C32 | 1.07584 (11) | 0.65097 (9) | 0.93950 (10) | 0.0149 (3) | |
H32 | 1.0278 | 0.6385 | 0.9423 | 0.018* | |
C33 | 0.90974 (10) | 0.68769 (9) | 0.77216 (10) | 0.0114 (3) | |
C34 | 0.82648 (11) | 0.67327 (9) | 0.71577 (10) | 0.0141 (3) | |
H34 | 0.8133 | 0.6307 | 0.6862 | 0.017* | |
C35 | 0.76280 (11) | 0.71868 (10) | 0.70163 (11) | 0.0169 (4) | |
H35 | 0.7074 | 0.7065 | 0.6636 | 0.020* | |
C36 | 0.77995 (11) | 0.78203 (10) | 0.74298 (11) | 0.0186 (4) | |
H36 | 0.7367 | 0.8134 | 0.7338 | 0.022* | |
C37 | 0.86115 (12) | 0.79827 (10) | 0.79769 (11) | 0.0198 (4) | |
H37 | 0.8740 | 0.8417 | 0.8256 | 0.024* | |
C38 | 0.92447 (11) | 0.75190 (9) | 0.81246 (11) | 0.0156 (4) | |
H38 | 0.9796 | 0.7643 | 0.8512 | 0.019* | |
C39 | 0.96464 (10) | 0.55282 (9) | 0.79114 (10) | 0.0125 (3) | |
C40 | 1.01674 (11) | 0.50062 (10) | 0.78853 (11) | 0.0168 (4) | |
H40 | 1.0613 | 0.5141 | 0.7801 | 0.020* | |
C41 | 1.00571 (12) | 0.43049 (10) | 0.79772 (11) | 0.0197 (4) | |
H41 | 1.0417 | 0.3970 | 0.7945 | 0.024* | |
C42 | 0.94228 (13) | 0.40910 (10) | 0.81155 (11) | 0.0220 (4) | |
H42 | 0.9343 | 0.3611 | 0.8175 | 0.026* | |
C43 | 0.89074 (12) | 0.45828 (10) | 0.81660 (11) | 0.0194 (4) | |
H43 | 0.8475 | 0.4442 | 0.8268 | 0.023* | |
C44 | 0.90227 (11) | 0.52917 (9) | 0.80670 (11) | 0.0161 (4) | |
H44 | 0.8664 | 0.5623 | 0.8107 | 0.019* | |
B2 | 0.46587 (12) | 0.61087 (10) | 0.28109 (11) | 0.0103 (4) | |
C45 | 0.54736 (10) | 0.59612 (9) | 0.37117 (10) | 0.0128 (3) | |
C46 | 0.62523 (11) | 0.57874 (9) | 0.38126 (11) | 0.0172 (4) | |
H46 | 0.6325 | 0.5783 | 0.3342 | 0.021* | |
C47 | 0.69209 (11) | 0.56207 (10) | 0.45750 (12) | 0.0220 (4) | |
H47 | 0.7439 | 0.5509 | 0.4618 | 0.026* | |
C48 | 0.68321 (12) | 0.56176 (10) | 0.52710 (12) | 0.0243 (4) | |
H48 | 0.7289 | 0.5509 | 0.5794 | 0.029* | |
C49 | 0.60724 (13) | 0.57734 (10) | 0.51991 (11) | 0.0225 (4) | |
H49 | 0.6003 | 0.5766 | 0.5672 | 0.027* | |
C50 | 0.54087 (11) | 0.59417 (10) | 0.44328 (11) | 0.0174 (4) | |
H50 | 0.4892 | 0.6048 | 0.4396 | 0.021* | |
C51 | 0.42408 (10) | 0.53399 (9) | 0.24948 (10) | 0.0118 (3) | |
C52 | 0.45417 (11) | 0.48859 (9) | 0.21120 (10) | 0.0156 (4) | |
H52 | 0.4961 | 0.5047 | 0.2001 | 0.019* | |
C53 | 0.42506 (12) | 0.42088 (10) | 0.18881 (11) | 0.0202 (4) | |
H53 | 0.4472 | 0.3919 | 0.1630 | 0.024* | |
C54 | 0.36389 (12) | 0.39573 (10) | 0.20406 (11) | 0.0233 (4) | |
H54 | 0.3433 | 0.3498 | 0.1881 | 0.028* | |
C55 | 0.33328 (12) | 0.43817 (10) | 0.24267 (11) | 0.0217 (4) | |
H55 | 0.2921 | 0.4211 | 0.2544 | 0.026* | |
C56 | 0.36271 (11) | 0.50610 (10) | 0.26462 (11) | 0.0167 (4) | |
H56 | 0.3404 | 0.5345 | 0.2907 | 0.020* | |
C57 | 0.40442 (10) | 0.66896 (9) | 0.28797 (10) | 0.0115 (3) | |
C58 | 0.31882 (11) | 0.67108 (9) | 0.23425 (10) | 0.0138 (3) | |
H58 | 0.2938 | 0.6343 | 0.1958 | 0.017* | |
C59 | 0.26885 (11) | 0.72536 (10) | 0.23514 (11) | 0.0177 (4) | |
H59 | 0.2112 | 0.7249 | 0.1978 | 0.021* | |
C60 | 0.30362 (12) | 0.77975 (10) | 0.29049 (11) | 0.0192 (4) | |
H60 | 0.2701 | 0.8166 | 0.2916 | 0.023* | |
C61 | 0.38795 (12) | 0.77961 (10) | 0.34415 (11) | 0.0179 (4) | |
H61 | 0.4126 | 0.8167 | 0.3822 | 0.021* | |
C62 | 0.43671 (11) | 0.72523 (9) | 0.34240 (10) | 0.0152 (4) | |
H62 | 0.4944 | 0.7264 | 0.3798 | 0.018* | |
C63 | 0.48849 (10) | 0.64604 (9) | 0.21412 (10) | 0.0118 (3) | |
C64 | 0.55235 (11) | 0.69427 (9) | 0.23561 (11) | 0.0160 (4) | |
H64 | 0.5889 | 0.7029 | 0.2924 | 0.019* | |
C65 | 0.56471 (11) | 0.73023 (10) | 0.17738 (12) | 0.0190 (4) | |
H65 | 0.6084 | 0.7630 | 0.1948 | 0.023* | |
C66 | 0.51356 (12) | 0.71822 (10) | 0.09466 (12) | 0.0197 (4) | |
H66 | 0.5219 | 0.7421 | 0.0546 | 0.024* | |
C67 | 0.44959 (11) | 0.67064 (10) | 0.07073 (11) | 0.0190 (4) | |
H67 | 0.4138 | 0.6619 | 0.0138 | 0.023* | |
C68 | 0.43761 (11) | 0.63595 (10) | 0.12913 (11) | 0.0155 (3) | |
H68 | 0.3931 | 0.6039 | 0.1110 | 0.019* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0144 (7) | 0.0150 (7) | 0.0125 (7) | 0.0008 (6) | 0.0063 (6) | 0.0005 (6) |
N2 | 0.0193 (8) | 0.0144 (7) | 0.0170 (7) | −0.0027 (6) | 0.0116 (6) | −0.0031 (6) |
N3 | 0.0141 (7) | 0.0123 (7) | 0.0149 (7) | 0.0010 (6) | 0.0078 (6) | 0.0015 (6) |
C1 | 0.0129 (8) | 0.0149 (8) | 0.0080 (7) | −0.0009 (7) | 0.0028 (7) | −0.0005 (6) |
C2 | 0.0196 (9) | 0.0250 (10) | 0.0174 (9) | 0.0078 (8) | 0.0096 (8) | 0.0017 (7) |
C3 | 0.0242 (10) | 0.0123 (9) | 0.0193 (9) | −0.0006 (7) | 0.0086 (8) | −0.0030 (7) |
C4 | 0.0281 (10) | 0.0217 (10) | 0.0213 (9) | −0.0056 (8) | 0.0175 (8) | −0.0019 (8) |
C5 | 0.0266 (10) | 0.0138 (9) | 0.0270 (10) | −0.0057 (7) | 0.0171 (9) | −0.0070 (7) |
C6 | 0.0286 (10) | 0.0133 (9) | 0.0267 (10) | 0.0034 (8) | 0.0164 (9) | 0.0018 (7) |
C7 | 0.0150 (9) | 0.0123 (8) | 0.0187 (9) | 0.0025 (7) | 0.0075 (7) | 0.0006 (7) |
C8 | 0.0170 (9) | 0.0112 (8) | 0.0165 (8) | −0.0011 (7) | 0.0098 (7) | −0.0014 (6) |
O1 | 0.0203 (7) | 0.0209 (7) | 0.0179 (6) | 0.0054 (5) | 0.0108 (6) | 0.0053 (5) |
O2 | 0.0187 (7) | 0.0171 (7) | 0.0243 (7) | 0.0026 (5) | 0.0144 (6) | 0.0062 (5) |
C9 | 0.0219 (10) | 0.0184 (9) | 0.0245 (9) | 0.0015 (7) | 0.0174 (8) | 0.0048 (7) |
C10 | 0.0275 (11) | 0.0218 (10) | 0.0284 (10) | −0.0031 (8) | 0.0142 (9) | 0.0038 (8) |
N4 | 0.0144 (7) | 0.0141 (7) | 0.0140 (7) | −0.0013 (6) | 0.0085 (6) | −0.0030 (6) |
N5 | 0.0192 (8) | 0.0233 (8) | 0.0123 (7) | 0.0010 (6) | 0.0079 (6) | 0.0004 (6) |
N6 | 0.0123 (7) | 0.0188 (8) | 0.0133 (7) | 0.0021 (6) | 0.0056 (6) | 0.0030 (6) |
C11 | 0.0153 (8) | 0.0084 (8) | 0.0134 (8) | 0.0020 (6) | 0.0069 (7) | 0.0023 (6) |
C12 | 0.0159 (9) | 0.0183 (9) | 0.0173 (8) | −0.0027 (7) | 0.0086 (7) | −0.0061 (7) |
C13 | 0.0136 (9) | 0.0192 (9) | 0.0193 (9) | −0.0004 (7) | 0.0097 (7) | −0.0023 (7) |
C14 | 0.0363 (12) | 0.0346 (12) | 0.0204 (9) | 0.0095 (9) | 0.0204 (9) | 0.0105 (9) |
C15 | 0.0231 (10) | 0.0330 (11) | 0.0142 (9) | 0.0029 (9) | 0.0012 (8) | −0.0061 (8) |
C16 | 0.0214 (10) | 0.0223 (10) | 0.0273 (10) | −0.0032 (8) | 0.0033 (9) | −0.0020 (8) |
C17 | 0.0122 (8) | 0.0181 (9) | 0.0179 (9) | 0.0023 (7) | 0.0043 (7) | 0.0044 (7) |
C18 | 0.0159 (9) | 0.0136 (8) | 0.0150 (8) | −0.0022 (7) | 0.0087 (7) | −0.0022 (7) |
O3 | 0.0179 (7) | 0.0206 (7) | 0.0178 (6) | 0.0036 (5) | 0.0104 (5) | 0.0033 (5) |
O4 | 0.0181 (6) | 0.0189 (7) | 0.0227 (7) | 0.0026 (5) | 0.0142 (6) | 0.0041 (5) |
C19 | 0.0222 (9) | 0.0163 (9) | 0.0205 (9) | −0.0009 (7) | 0.0157 (8) | 0.0009 (7) |
C20 | 0.0295 (11) | 0.0186 (10) | 0.0253 (10) | −0.0027 (8) | 0.0181 (9) | −0.0027 (8) |
B1 | 0.0122 (9) | 0.0110 (9) | 0.0111 (8) | 0.0009 (7) | 0.0061 (7) | −0.0004 (7) |
C21 | 0.0091 (8) | 0.0154 (8) | 0.0124 (8) | 0.0028 (6) | 0.0046 (7) | 0.0006 (6) |
C22 | 0.0146 (9) | 0.0169 (9) | 0.0153 (8) | −0.0017 (7) | 0.0068 (7) | −0.0005 (7) |
C23 | 0.0186 (9) | 0.0206 (9) | 0.0196 (9) | −0.0018 (7) | 0.0099 (8) | 0.0042 (7) |
C24 | 0.0164 (9) | 0.0268 (10) | 0.0111 (8) | 0.0058 (7) | 0.0080 (7) | 0.0035 (7) |
C25 | 0.0168 (9) | 0.0213 (9) | 0.0113 (8) | 0.0027 (7) | 0.0039 (7) | −0.0031 (7) |
C26 | 0.0155 (9) | 0.0123 (8) | 0.0154 (8) | −0.0002 (7) | 0.0072 (7) | −0.0006 (7) |
C27 | 0.0142 (8) | 0.0081 (8) | 0.0124 (8) | 0.0022 (6) | 0.0052 (7) | 0.0007 (6) |
C28 | 0.0156 (9) | 0.0146 (8) | 0.0135 (8) | 0.0005 (7) | 0.0068 (7) | −0.0008 (6) |
C29 | 0.0119 (8) | 0.0159 (9) | 0.0208 (9) | 0.0005 (7) | 0.0063 (7) | −0.0005 (7) |
C30 | 0.0150 (9) | 0.0117 (8) | 0.0148 (8) | 0.0026 (7) | 0.0016 (7) | −0.0003 (6) |
C31 | 0.0241 (10) | 0.0131 (8) | 0.0116 (8) | 0.0043 (7) | 0.0070 (7) | 0.0012 (6) |
C32 | 0.0155 (8) | 0.0133 (8) | 0.0163 (8) | 0.0013 (7) | 0.0081 (7) | 0.0006 (7) |
C33 | 0.0140 (8) | 0.0124 (8) | 0.0105 (7) | 0.0006 (6) | 0.0079 (7) | 0.0020 (6) |
C34 | 0.0151 (8) | 0.0149 (8) | 0.0122 (8) | −0.0018 (7) | 0.0067 (7) | −0.0015 (6) |
C35 | 0.0123 (8) | 0.0248 (10) | 0.0142 (8) | 0.0006 (7) | 0.0070 (7) | 0.0028 (7) |
C36 | 0.0189 (9) | 0.0195 (9) | 0.0206 (9) | 0.0096 (7) | 0.0121 (8) | 0.0072 (7) |
C37 | 0.0272 (10) | 0.0112 (9) | 0.0202 (9) | 0.0034 (7) | 0.0109 (8) | 0.0007 (7) |
C38 | 0.0135 (8) | 0.0150 (9) | 0.0161 (8) | −0.0008 (7) | 0.0054 (7) | −0.0014 (7) |
C39 | 0.0150 (8) | 0.0135 (8) | 0.0078 (7) | 0.0005 (7) | 0.0045 (7) | −0.0004 (6) |
C40 | 0.0179 (9) | 0.0182 (9) | 0.0151 (8) | 0.0019 (7) | 0.0086 (7) | 0.0002 (7) |
C41 | 0.0260 (10) | 0.0153 (9) | 0.0141 (8) | 0.0078 (7) | 0.0068 (8) | 0.0013 (7) |
C42 | 0.0344 (11) | 0.0129 (9) | 0.0138 (8) | −0.0025 (8) | 0.0080 (8) | 0.0012 (7) |
C43 | 0.0255 (10) | 0.0172 (9) | 0.0179 (9) | −0.0056 (8) | 0.0124 (8) | 0.0008 (7) |
C44 | 0.0202 (9) | 0.0140 (8) | 0.0155 (8) | −0.0003 (7) | 0.0098 (7) | −0.0015 (7) |
B2 | 0.0113 (9) | 0.0102 (9) | 0.0098 (8) | −0.0013 (7) | 0.0055 (7) | −0.0015 (7) |
C45 | 0.0134 (8) | 0.0090 (8) | 0.0130 (8) | −0.0008 (6) | 0.0042 (7) | −0.0030 (6) |
C46 | 0.0160 (9) | 0.0118 (8) | 0.0208 (9) | −0.0004 (7) | 0.0067 (8) | −0.0028 (7) |
C47 | 0.0126 (9) | 0.0141 (9) | 0.0281 (10) | 0.0017 (7) | 0.0012 (8) | −0.0037 (8) |
C48 | 0.0239 (10) | 0.0123 (9) | 0.0179 (9) | 0.0014 (7) | −0.0045 (8) | −0.0032 (7) |
C49 | 0.0310 (11) | 0.0184 (10) | 0.0122 (8) | 0.0024 (8) | 0.0059 (8) | −0.0010 (7) |
C50 | 0.0181 (9) | 0.0166 (9) | 0.0155 (8) | 0.0016 (7) | 0.0066 (7) | −0.0011 (7) |
C51 | 0.0107 (8) | 0.0134 (8) | 0.0066 (7) | −0.0004 (6) | 0.0006 (6) | 0.0006 (6) |
C52 | 0.0136 (8) | 0.0160 (9) | 0.0136 (8) | 0.0026 (7) | 0.0038 (7) | 0.0005 (7) |
C53 | 0.0209 (10) | 0.0141 (9) | 0.0166 (9) | 0.0030 (7) | 0.0022 (8) | −0.0031 (7) |
C54 | 0.0232 (10) | 0.0122 (9) | 0.0192 (9) | −0.0028 (7) | −0.0015 (8) | 0.0007 (7) |
C55 | 0.0180 (9) | 0.0203 (10) | 0.0190 (9) | −0.0067 (8) | 0.0029 (8) | 0.0052 (7) |
C56 | 0.0172 (9) | 0.0176 (9) | 0.0139 (8) | −0.0017 (7) | 0.0065 (7) | 0.0020 (7) |
C57 | 0.0139 (8) | 0.0123 (8) | 0.0109 (7) | 0.0000 (6) | 0.0082 (7) | 0.0022 (6) |
C58 | 0.0163 (9) | 0.0152 (8) | 0.0122 (8) | 0.0003 (7) | 0.0087 (7) | 0.0027 (6) |
C59 | 0.0156 (9) | 0.0239 (10) | 0.0161 (8) | 0.0062 (7) | 0.0096 (7) | 0.0098 (7) |
C60 | 0.0273 (10) | 0.0191 (9) | 0.0203 (9) | 0.0106 (8) | 0.0186 (8) | 0.0086 (7) |
C61 | 0.0293 (10) | 0.0138 (9) | 0.0152 (8) | 0.0018 (7) | 0.0145 (8) | 0.0003 (7) |
C62 | 0.0166 (9) | 0.0160 (9) | 0.0130 (8) | 0.0004 (7) | 0.0073 (7) | 0.0011 (7) |
C63 | 0.0105 (8) | 0.0113 (8) | 0.0151 (8) | 0.0030 (6) | 0.0075 (7) | 0.0000 (6) |
C64 | 0.0148 (9) | 0.0157 (9) | 0.0180 (9) | 0.0001 (7) | 0.0086 (7) | −0.0022 (7) |
C65 | 0.0167 (9) | 0.0156 (9) | 0.0303 (10) | −0.0014 (7) | 0.0159 (8) | 0.0002 (8) |
C66 | 0.0233 (10) | 0.0187 (9) | 0.0267 (10) | 0.0068 (8) | 0.0196 (8) | 0.0064 (8) |
C67 | 0.0186 (9) | 0.0236 (10) | 0.0151 (8) | 0.0047 (7) | 0.0086 (8) | 0.0022 (7) |
C68 | 0.0132 (8) | 0.0176 (9) | 0.0154 (8) | −0.0008 (7) | 0.0069 (7) | −0.0005 (7) |
N1—C1 | 1.323 (2) | C25—H25 | 0.9500 |
N1—C3 | 1.460 (2) | C26—H26 | 0.9500 |
N1—C2 | 1.465 (2) | C27—C28 | 1.400 (2) |
N2—C1 | 1.333 (2) | C27—C32 | 1.404 (2) |
N2—C4 | 1.464 (2) | C28—C29 | 1.398 (2) |
N2—C5 | 1.477 (2) | C28—H28 | 0.9500 |
N3—C1 | 1.379 (2) | C29—C30 | 1.382 (3) |
N3—C8 | 1.406 (2) | C29—H29 | 0.9500 |
N3—C7 | 1.495 (2) | C30—C31 | 1.391 (3) |
C2—H2A | 0.9800 | C30—H30 | 0.9500 |
C2—H2B | 0.9800 | C31—C32 | 1.388 (2) |
C2—H2C | 0.9800 | C31—H31 | 0.9500 |
C3—H3A | 0.9800 | C32—H32 | 0.9500 |
C3—H3B | 0.9800 | C33—C38 | 1.400 (2) |
C3—H3C | 0.9800 | C33—C34 | 1.408 (2) |
C4—H4A | 0.9800 | C34—C35 | 1.387 (3) |
C4—H4B | 0.9800 | C34—H34 | 0.9500 |
C4—H4C | 0.9800 | C35—C36 | 1.391 (3) |
C5—C6 | 1.511 (3) | C35—H35 | 0.9500 |
C5—H5A | 0.9900 | C36—C37 | 1.381 (3) |
C5—H5B | 0.9900 | C36—H36 | 0.9500 |
C6—C7 | 1.521 (3) | C37—C38 | 1.391 (3) |
C6—H6A | 0.9900 | C37—H37 | 0.9500 |
C6—H6B | 0.9900 | C38—H38 | 0.9500 |
C7—H7A | 0.9900 | C39—C44 | 1.400 (2) |
C7—H7B | 0.9900 | C39—C40 | 1.411 (2) |
C8—O1 | 1.199 (2) | C40—C41 | 1.386 (3) |
C8—O2 | 1.331 (2) | C40—H40 | 0.9500 |
O2—C9 | 1.465 (2) | C41—C42 | 1.386 (3) |
C9—C10 | 1.499 (3) | C41—H41 | 0.9500 |
C9—H9A | 0.9900 | C42—C43 | 1.380 (3) |
C9—H9B | 0.9900 | C42—H42 | 0.9500 |
C10—H10A | 0.9800 | C43—C44 | 1.405 (3) |
C10—H10B | 0.9800 | C43—H43 | 0.9500 |
C10—H10C | 0.9800 | C44—H44 | 0.9500 |
N4—C11 | 1.326 (2) | B2—C51 | 1.638 (2) |
N4—C12 | 1.464 (2) | B2—C63 | 1.643 (2) |
N4—C13 | 1.472 (2) | B2—C45 | 1.643 (2) |
N5—C11 | 1.324 (2) | B2—C57 | 1.645 (2) |
N5—C14 | 1.463 (2) | C45—C46 | 1.405 (2) |
N5—C15 | 1.474 (2) | C45—C50 | 1.405 (2) |
N6—C11 | 1.381 (2) | C46—C47 | 1.391 (3) |
N6—C18 | 1.409 (2) | C46—H46 | 0.9500 |
N6—C17 | 1.482 (2) | C47—C48 | 1.384 (3) |
C12—H12A | 0.9800 | C47—H47 | 0.9500 |
C12—H12B | 0.9800 | C48—C49 | 1.383 (3) |
C12—H12C | 0.9800 | C48—H48 | 0.9500 |
C13—H13A | 0.9800 | C49—C50 | 1.392 (3) |
C13—H13B | 0.9800 | C49—H49 | 0.9500 |
C13—H13C | 0.9800 | C50—H50 | 0.9500 |
C14—H14A | 0.9800 | C51—C52 | 1.404 (2) |
C14—H14B | 0.9800 | C51—C56 | 1.407 (2) |
C14—H14C | 0.9800 | C52—C53 | 1.392 (3) |
C15—C16 | 1.506 (3) | C52—H52 | 0.9500 |
C15—H15A | 0.9900 | C53—C54 | 1.386 (3) |
C15—H15B | 0.9900 | C53—H53 | 0.9500 |
C16—C17 | 1.501 (3) | C54—C55 | 1.380 (3) |
C16—H16A | 0.9900 | C54—H54 | 0.9500 |
C16—H16B | 0.9900 | C55—C56 | 1.397 (3) |
C17—H17A | 0.9900 | C55—H55 | 0.9500 |
C17—H17B | 0.9900 | C56—H56 | 0.9500 |
C18—O3 | 1.202 (2) | C57—C62 | 1.400 (2) |
C18—O4 | 1.329 (2) | C57—C58 | 1.405 (2) |
O4—C19 | 1.456 (2) | C58—C59 | 1.402 (3) |
C19—C20 | 1.504 (3) | C58—H58 | 0.9500 |
C19—H19A | 0.9900 | C59—C60 | 1.386 (3) |
C19—H19B | 0.9900 | C59—H59 | 0.9500 |
C20—H20A | 0.9800 | C60—C61 | 1.386 (3) |
C20—H20B | 0.9800 | C60—H60 | 0.9500 |
C20—H20C | 0.9800 | C61—C62 | 1.393 (3) |
B1—C27 | 1.640 (2) | C61—H61 | 0.9500 |
B1—C33 | 1.640 (2) | C62—H62 | 0.9500 |
B1—C21 | 1.644 (2) | C63—C64 | 1.401 (2) |
B1—C39 | 1.645 (3) | C63—C68 | 1.404 (2) |
C21—C26 | 1.399 (2) | C64—C65 | 1.396 (3) |
C21—C22 | 1.408 (2) | C64—H64 | 0.9500 |
C22—C23 | 1.387 (3) | C65—C66 | 1.377 (3) |
C22—H22 | 0.9500 | C65—H65 | 0.9500 |
C23—C24 | 1.384 (3) | C66—C67 | 1.389 (3) |
C23—H23 | 0.9500 | C66—H66 | 0.9500 |
C24—C25 | 1.385 (3) | C67—C68 | 1.383 (3) |
C24—H24 | 0.9500 | C67—H67 | 0.9500 |
C25—C26 | 1.390 (2) | C68—H68 | 0.9500 |
C1—N1—C3 | 123.43 (15) | C22—C23—H23 | 120.0 |
C1—N1—C2 | 122.60 (15) | C23—C24—C25 | 119.17 (16) |
C3—N1—C2 | 113.85 (15) | C23—C24—H24 | 120.4 |
C1—N2—C4 | 122.45 (15) | C25—C24—H24 | 120.4 |
C1—N2—C5 | 115.92 (14) | C24—C25—C26 | 120.10 (17) |
C4—N2—C5 | 117.00 (15) | C24—C25—H25 | 119.9 |
C1—N3—C8 | 120.35 (14) | C26—C25—H25 | 119.9 |
C1—N3—C7 | 120.94 (14) | C25—C26—C21 | 122.79 (17) |
C8—N3—C7 | 118.37 (14) | C25—C26—H26 | 118.6 |
N1—C1—N2 | 122.69 (16) | C21—C26—H26 | 118.6 |
N1—C1—N3 | 120.46 (15) | C28—C27—C32 | 115.13 (15) |
N2—C1—N3 | 116.84 (15) | C28—C27—B1 | 126.56 (15) |
N1—C2—H2A | 109.5 | C32—C27—B1 | 118.29 (15) |
N1—C2—H2B | 109.5 | C29—C28—C27 | 122.91 (16) |
H2A—C2—H2B | 109.5 | C29—C28—H28 | 118.5 |
N1—C2—H2C | 109.5 | C27—C28—H28 | 118.5 |
H2A—C2—H2C | 109.5 | C30—C29—C28 | 119.99 (17) |
H2B—C2—H2C | 109.5 | C30—C29—H29 | 120.0 |
N1—C3—H3A | 109.5 | C28—C29—H29 | 120.0 |
N1—C3—H3B | 109.5 | C29—C30—C31 | 118.90 (16) |
H3A—C3—H3B | 109.5 | C29—C30—H30 | 120.5 |
N1—C3—H3C | 109.5 | C31—C30—H30 | 120.5 |
H3A—C3—H3C | 109.5 | C32—C31—C30 | 120.24 (16) |
H3B—C3—H3C | 109.5 | C32—C31—H31 | 119.9 |
N2—C4—H4A | 109.5 | C30—C31—H31 | 119.9 |
N2—C4—H4B | 109.5 | C31—C32—C27 | 122.83 (17) |
H4A—C4—H4B | 109.5 | C31—C32—H32 | 118.6 |
N2—C4—H4C | 109.5 | C27—C32—H32 | 118.6 |
H4A—C4—H4C | 109.5 | C38—C33—C34 | 115.37 (15) |
H4B—C4—H4C | 109.5 | C38—C33—B1 | 124.00 (15) |
N2—C5—C6 | 106.66 (15) | C34—C33—B1 | 120.32 (15) |
N2—C5—H5A | 110.4 | C35—C34—C33 | 122.77 (16) |
C6—C5—H5A | 110.4 | C35—C34—H34 | 118.6 |
N2—C5—H5B | 110.4 | C33—C34—H34 | 118.6 |
C6—C5—H5B | 110.4 | C34—C35—C36 | 120.13 (17) |
H5A—C5—H5B | 108.6 | C34—C35—H35 | 119.9 |
C5—C6—C7 | 108.33 (15) | C36—C35—H35 | 119.9 |
C5—C6—H6A | 110.0 | C37—C36—C35 | 118.53 (17) |
C7—C6—H6A | 110.0 | C37—C36—H36 | 120.7 |
C5—C6—H6B | 110.0 | C35—C36—H36 | 120.7 |
C7—C6—H6B | 110.0 | C36—C37—C38 | 120.91 (17) |
H6A—C6—H6B | 108.4 | C36—C37—H37 | 119.5 |
N3—C7—C6 | 111.26 (15) | C38—C37—H37 | 119.5 |
N3—C7—H7A | 109.4 | C37—C38—C33 | 122.27 (17) |
C6—C7—H7A | 109.4 | C37—C38—H38 | 118.9 |
N3—C7—H7B | 109.4 | C33—C38—H38 | 118.9 |
C6—C7—H7B | 109.4 | C44—C39—C40 | 115.27 (16) |
H7A—C7—H7B | 108.0 | C44—C39—B1 | 125.15 (15) |
O1—C8—O2 | 126.89 (16) | C40—C39—B1 | 119.51 (15) |
O1—C8—N3 | 124.10 (16) | C41—C40—C39 | 122.80 (17) |
O2—C8—N3 | 109.02 (14) | C41—C40—H40 | 118.6 |
C8—O2—C9 | 115.89 (14) | C39—C40—H40 | 118.6 |
O2—C9—C10 | 110.73 (15) | C42—C41—C40 | 120.11 (18) |
O2—C9—H9A | 109.5 | C42—C41—H41 | 119.9 |
C10—C9—H9A | 109.5 | C40—C41—H41 | 119.9 |
O2—C9—H9B | 109.5 | C43—C42—C41 | 119.36 (18) |
C10—C9—H9B | 109.5 | C43—C42—H42 | 120.3 |
H9A—C9—H9B | 108.1 | C41—C42—H42 | 120.3 |
C9—C10—H10A | 109.5 | C42—C43—C44 | 119.98 (18) |
C9—C10—H10B | 109.5 | C42—C43—H43 | 120.0 |
H10A—C10—H10B | 109.5 | C44—C43—H43 | 120.0 |
C9—C10—H10C | 109.5 | C39—C44—C43 | 122.44 (17) |
H10A—C10—H10C | 109.5 | C39—C44—H44 | 118.8 |
H10B—C10—H10C | 109.5 | C43—C44—H44 | 118.8 |
C11—N4—C12 | 121.76 (15) | C51—B2—C63 | 110.53 (13) |
C11—N4—C13 | 122.96 (14) | C51—B2—C45 | 104.41 (13) |
C12—N4—C13 | 114.62 (14) | C63—B2—C45 | 113.29 (14) |
C11—N5—C14 | 121.88 (16) | C51—B2—C57 | 114.51 (14) |
C11—N5—C15 | 123.72 (16) | C63—B2—C57 | 102.97 (13) |
C14—N5—C15 | 114.09 (15) | C45—B2—C57 | 111.43 (13) |
C11—N6—C18 | 118.74 (14) | C46—C45—C50 | 115.44 (16) |
C11—N6—C17 | 116.00 (14) | C46—C45—B2 | 123.48 (15) |
C18—N6—C17 | 118.83 (14) | C50—C45—B2 | 120.84 (15) |
N5—C11—N4 | 122.18 (16) | C47—C46—C45 | 122.56 (18) |
N5—C11—N6 | 117.57 (15) | C47—C46—H46 | 118.7 |
N4—C11—N6 | 120.11 (15) | C45—C46—H46 | 118.7 |
N4—C12—H12A | 109.5 | C48—C47—C46 | 120.02 (18) |
N4—C12—H12B | 109.5 | C48—C47—H47 | 120.0 |
H12A—C12—H12B | 109.5 | C46—C47—H47 | 120.0 |
N4—C12—H12C | 109.5 | C49—C48—C47 | 119.43 (17) |
H12A—C12—H12C | 109.5 | C49—C48—H48 | 120.3 |
H12B—C12—H12C | 109.5 | C47—C48—H48 | 120.3 |
N4—C13—H13A | 109.5 | C48—C49—C50 | 119.97 (18) |
N4—C13—H13B | 109.5 | C48—C49—H49 | 120.0 |
H13A—C13—H13B | 109.5 | C50—C49—H49 | 120.0 |
N4—C13—H13C | 109.5 | C49—C50—C45 | 122.54 (18) |
H13A—C13—H13C | 109.5 | C49—C50—H50 | 118.7 |
H13B—C13—H13C | 109.5 | C45—C50—H50 | 118.7 |
N5—C14—H14A | 109.5 | C52—C51—C56 | 115.31 (16) |
N5—C14—H14B | 109.5 | C52—C51—B2 | 120.42 (15) |
H14A—C14—H14B | 109.5 | C56—C51—B2 | 124.02 (15) |
N5—C14—H14C | 109.5 | C53—C52—C51 | 122.68 (17) |
H14A—C14—H14C | 109.5 | C53—C52—H52 | 118.7 |
H14B—C14—H14C | 109.5 | C51—C52—H52 | 118.7 |
N5—C15—C16 | 113.56 (16) | C54—C53—C52 | 120.12 (18) |
N5—C15—H15A | 108.9 | C54—C53—H53 | 119.9 |
C16—C15—H15A | 108.9 | C52—C53—H53 | 119.9 |
N5—C15—H15B | 108.9 | C55—C54—C53 | 119.23 (17) |
C16—C15—H15B | 108.9 | C55—C54—H54 | 120.4 |
H15A—C15—H15B | 107.7 | C53—C54—H54 | 120.4 |
C17—C16—C15 | 108.01 (17) | C54—C55—C56 | 120.19 (18) |
C17—C16—H16A | 110.1 | C54—C55—H55 | 119.9 |
C15—C16—H16A | 110.1 | C56—C55—H55 | 119.9 |
C17—C16—H16B | 110.1 | C55—C56—C51 | 122.46 (18) |
C15—C16—H16B | 110.1 | C55—C56—H56 | 118.8 |
H16A—C16—H16B | 108.4 | C51—C56—H56 | 118.8 |
N6—C17—C16 | 105.98 (15) | C62—C57—C58 | 115.31 (16) |
N6—C17—H17A | 110.5 | C62—C57—B2 | 120.82 (15) |
C16—C17—H17A | 110.5 | C58—C57—B2 | 123.41 (15) |
N6—C17—H17B | 110.5 | C59—C58—C57 | 122.58 (17) |
C16—C17—H17B | 110.5 | C59—C58—H58 | 118.7 |
H17A—C17—H17B | 108.7 | C57—C58—H58 | 118.7 |
O3—C18—O4 | 126.37 (16) | C60—C59—C58 | 119.97 (17) |
O3—C18—N6 | 124.48 (16) | C60—C59—H59 | 120.0 |
O4—C18—N6 | 109.15 (15) | C58—C59—H59 | 120.0 |
C18—O4—C19 | 115.60 (14) | C59—C60—C61 | 119.07 (17) |
O4—C19—C20 | 110.62 (15) | C59—C60—H60 | 120.5 |
O4—C19—H19A | 109.5 | C61—C60—H60 | 120.5 |
C20—C19—H19A | 109.5 | C60—C61—C62 | 120.19 (17) |
O4—C19—H19B | 109.5 | C60—C61—H61 | 119.9 |
C20—C19—H19B | 109.5 | C62—C61—H61 | 119.9 |
H19A—C19—H19B | 108.1 | C61—C62—C57 | 122.88 (17) |
C19—C20—H20A | 109.5 | C61—C62—H62 | 118.6 |
C19—C20—H20B | 109.5 | C57—C62—H62 | 118.6 |
H20A—C20—H20B | 109.5 | C64—C63—C68 | 114.99 (16) |
C19—C20—H20C | 109.5 | C64—C63—B2 | 123.41 (15) |
H20A—C20—H20C | 109.5 | C68—C63—B2 | 121.14 (15) |
H20B—C20—H20C | 109.5 | C65—C64—C63 | 122.94 (17) |
C27—B1—C33 | 110.48 (14) | C65—C64—H64 | 118.5 |
C27—B1—C21 | 114.04 (14) | C63—C64—H64 | 118.5 |
C33—B1—C21 | 102.80 (13) | C66—C65—C64 | 119.99 (17) |
C27—B1—C39 | 106.22 (13) | C66—C65—H65 | 120.0 |
C33—B1—C39 | 113.27 (14) | C64—C65—H65 | 120.0 |
C21—B1—C39 | 110.23 (14) | C65—C66—C67 | 118.89 (17) |
C26—C21—C22 | 115.13 (15) | C65—C66—H66 | 120.6 |
C26—C21—B1 | 122.76 (15) | C67—C66—H66 | 120.6 |
C22—C21—B1 | 121.83 (15) | C68—C67—C66 | 120.45 (17) |
C23—C22—C21 | 122.84 (17) | C68—C67—H67 | 119.8 |
C23—C22—H22 | 118.6 | C66—C67—H67 | 119.8 |
C21—C22—H22 | 118.6 | C67—C68—C63 | 122.73 (17) |
C24—C23—C22 | 119.94 (17) | C67—C68—H68 | 118.6 |
C24—C23—H23 | 120.0 | C63—C68—H68 | 118.6 |
C3—N1—C1—N2 | −157.48 (16) | C27—B1—C33—C34 | −168.69 (15) |
C2—N1—C1—N2 | 26.7 (2) | C21—B1—C33—C34 | 69.26 (18) |
C3—N1—C1—N3 | 21.4 (2) | C39—B1—C33—C34 | −49.7 (2) |
C2—N1—C1—N3 | −154.40 (15) | C38—C33—C34—C35 | −1.0 (2) |
C4—N2—C1—N1 | 33.4 (3) | B1—C33—C34—C35 | −174.89 (16) |
C5—N2—C1—N1 | −171.44 (16) | C33—C34—C35—C36 | 1.0 (3) |
C4—N2—C1—N3 | −145.49 (17) | C34—C35—C36—C37 | 0.1 (3) |
C5—N2—C1—N3 | 9.6 (2) | C35—C36—C37—C38 | −1.2 (3) |
C8—N3—C1—N1 | 41.4 (2) | C36—C37—C38—C33 | 1.1 (3) |
C7—N3—C1—N1 | −145.28 (16) | C34—C33—C38—C37 | −0.1 (2) |
C8—N3—C1—N2 | −139.61 (16) | B1—C33—C38—C37 | 173.56 (16) |
C7—N3—C1—N2 | 33.7 (2) | C27—B1—C39—C44 | 110.49 (18) |
C1—N2—C5—C6 | −58.4 (2) | C33—B1—C39—C44 | −11.0 (2) |
C4—N2—C5—C6 | 98.17 (18) | C21—B1—C39—C44 | −125.50 (17) |
N2—C5—C6—C7 | 63.43 (19) | C27—B1—C39—C40 | −66.51 (18) |
C1—N3—C7—C6 | −23.6 (2) | C33—B1—C39—C40 | 172.05 (14) |
C8—N3—C7—C6 | 149.82 (16) | C21—B1—C39—C40 | 57.5 (2) |
C5—C6—C7—N3 | −25.2 (2) | C44—C39—C40—C41 | 2.2 (2) |
C1—N3—C8—O1 | 16.0 (3) | B1—C39—C40—C41 | 179.49 (16) |
C7—N3—C8—O1 | −157.45 (17) | C39—C40—C41—C42 | −1.1 (3) |
C1—N3—C8—O2 | −164.46 (15) | C40—C41—C42—C43 | −0.4 (3) |
C7—N3—C8—O2 | 22.1 (2) | C41—C42—C43—C44 | 0.8 (3) |
O1—C8—O2—C9 | 3.0 (3) | C40—C39—C44—C43 | −1.8 (2) |
N3—C8—O2—C9 | −176.55 (14) | B1—C39—C44—C43 | −178.92 (16) |
C8—O2—C9—C10 | −84.87 (19) | C42—C43—C44—C39 | 0.4 (3) |
C14—N5—C11—N4 | 19.6 (3) | C51—B2—C45—C46 | 88.03 (19) |
C15—N5—C11—N4 | −167.15 (17) | C63—B2—C45—C46 | −32.3 (2) |
C14—N5—C11—N6 | −155.88 (17) | C57—B2—C45—C46 | −147.84 (16) |
C15—N5—C11—N6 | 17.3 (3) | C51—B2—C45—C50 | −86.17 (18) |
C12—N4—C11—N5 | −152.35 (17) | C63—B2—C45—C50 | 153.51 (16) |
C13—N4—C11—N5 | 37.4 (3) | C57—B2—C45—C50 | 38.0 (2) |
C12—N4—C11—N6 | 23.1 (2) | C50—C45—C46—C47 | −1.3 (3) |
C13—N4—C11—N6 | −147.19 (16) | B2—C45—C46—C47 | −175.75 (16) |
C18—N6—C11—N5 | −133.56 (17) | C45—C46—C47—C48 | 0.4 (3) |
C17—N6—C11—N5 | 18.0 (2) | C46—C47—C48—C49 | 0.7 (3) |
C18—N6—C11—N4 | 50.8 (2) | C47—C48—C49—C50 | −1.0 (3) |
C17—N6—C11—N4 | −157.63 (16) | C48—C49—C50—C45 | 0.1 (3) |
C11—N5—C15—C16 | −8.6 (3) | C46—C45—C50—C49 | 1.0 (3) |
C14—N5—C15—C16 | 165.11 (18) | B2—C45—C50—C49 | 175.67 (17) |
N5—C15—C16—C17 | −32.7 (2) | C63—B2—C51—C52 | 39.9 (2) |
C11—N6—C17—C16 | −58.6 (2) | C45—B2—C51—C52 | −82.29 (18) |
C18—N6—C17—C16 | 92.93 (19) | C57—B2—C51—C52 | 155.59 (15) |
C15—C16—C17—N6 | 63.05 (19) | C63—B2—C51—C56 | −146.22 (16) |
C11—N6—C18—O3 | −3.9 (3) | C45—B2—C51—C56 | 91.62 (18) |
C17—N6—C18—O3 | −154.68 (17) | C57—B2—C51—C56 | −30.5 (2) |
C11—N6—C18—O4 | 176.03 (15) | C56—C51—C52—C53 | 0.6 (2) |
C17—N6—C18—O4 | 25.3 (2) | B2—C51—C52—C53 | 175.06 (15) |
O3—C18—O4—C19 | 7.9 (3) | C51—C52—C53—C54 | 0.0 (3) |
N6—C18—O4—C19 | −172.08 (14) | C52—C53—C54—C55 | −1.0 (3) |
C18—O4—C19—C20 | 80.33 (19) | C53—C54—C55—C56 | 1.2 (3) |
C27—B1—C21—C26 | 137.68 (16) | C54—C55—C56—C51 | −0.5 (3) |
C33—B1—C21—C26 | −102.71 (18) | C52—C51—C56—C55 | −0.4 (2) |
C39—B1—C21—C26 | 18.3 (2) | B2—C51—C56—C55 | −174.60 (16) |
C27—B1—C21—C22 | −48.7 (2) | C51—B2—C57—C62 | 154.21 (15) |
C33—B1—C21—C22 | 70.94 (19) | C63—B2—C57—C62 | −85.76 (17) |
C39—B1—C21—C22 | −168.04 (15) | C45—B2—C57—C62 | 36.0 (2) |
C26—C21—C22—C23 | −2.1 (3) | C51—B2—C57—C58 | −33.9 (2) |
B1—C21—C22—C23 | −176.23 (16) | C63—B2—C57—C58 | 86.11 (18) |
C21—C22—C23—C24 | 1.5 (3) | C45—B2—C57—C58 | −152.13 (15) |
C22—C23—C24—C25 | 0.4 (3) | C62—C57—C58—C59 | −0.4 (2) |
C23—C24—C25—C26 | −1.4 (3) | B2—C57—C58—C59 | −172.67 (15) |
C24—C25—C26—C21 | 0.6 (3) | C57—C58—C59—C60 | 0.0 (3) |
C22—C21—C26—C25 | 1.1 (3) | C58—C59—C60—C61 | 0.3 (3) |
B1—C21—C26—C25 | 175.13 (16) | C59—C60—C61—C62 | −0.3 (3) |
C33—B1—C27—C28 | −121.25 (18) | C60—C61—C62—C57 | −0.1 (3) |
C21—B1—C27—C28 | −6.1 (2) | C58—C57—C62—C61 | 0.4 (2) |
C39—B1—C27—C28 | 115.53 (18) | B2—C57—C62—C61 | 172.91 (16) |
C33—B1—C27—C32 | 60.7 (2) | C51—B2—C63—C64 | −152.35 (16) |
C21—B1—C27—C32 | 175.83 (15) | C45—B2—C63—C64 | −35.6 (2) |
C39—B1—C27—C32 | −62.57 (19) | C57—B2—C63—C64 | 84.91 (19) |
C32—C27—C28—C29 | −0.3 (3) | C51—B2—C63—C68 | 35.8 (2) |
B1—C27—C28—C29 | −178.48 (16) | C45—B2—C63—C68 | 152.59 (15) |
C27—C28—C29—C30 | 0.1 (3) | C57—B2—C63—C68 | −86.92 (18) |
C28—C29—C30—C31 | 0.4 (3) | C68—C63—C64—C65 | 0.4 (3) |
C29—C30—C31—C32 | −0.5 (3) | B2—C63—C64—C65 | −171.90 (16) |
C30—C31—C32—C27 | 0.2 (3) | C63—C64—C65—C66 | −0.9 (3) |
C28—C27—C32—C31 | 0.2 (3) | C64—C65—C66—C67 | 0.7 (3) |
B1—C27—C32—C31 | 178.48 (16) | C65—C66—C67—C68 | 0.0 (3) |
C27—B1—C33—C38 | 18.0 (2) | C66—C67—C68—C63 | −0.5 (3) |
C21—B1—C33—C38 | −104.06 (18) | C64—C63—C68—C67 | 0.3 (3) |
C39—B1—C33—C38 | 137.01 (16) | B2—C63—C68—C67 | 172.78 (16) |
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 | D···A | D—H···A |
C5—H5A···Cg1 | 0.99 | 2.77 | 3.502 (3) | 131 |
C19—H19B···Cg1 | 0.99 | 2.86 | 3.559 (3) | 128 |
C17—H17B···Cg2 | 0.99 | 2.67 | 3.632 (3) | 165 |
C6—H6B···Cg3 | 0.99 | 2.75 | 3.624 (3) | 147 |
C13—H13C···Cg3 | 0.98 | 2.72 | 3.421 (3) | 129 |
C13—H13B···Cg4 | 0.98 | 2.67 | 3.583 (3) | 154 |
C12—H12C···Cg5 | 0.98 | 2.70 | 3.329 (3) | 121 |
C14—H14B···Cg5 | 0.98 | 2.76 | 3.354 (3) | 120 |
C12—H12B···Cg6 | 0.98 | 2.64 | 3.535 (3) | 151 |
C9—H9A···Cg6 | 0.99 | 2.75 | 3.655 (3) | 151 |
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 | D···A | D—H···A |
C5—H5A···Cg1 | 0.99 | 2.77 | 3.502 (3) | 131 |
C19—H19B···Cg1 | 0.99 | 2.86 | 3.559 (3) | 128 |
C17—H17B···Cg2 | 0.99 | 2.67 | 3.632 (3) | 165 |
C6—H6B···Cg3 | 0.99 | 2.75 | 3.624 (3) | 147 |
C13—H13C···Cg3 | 0.98 | 2.72 | 3.421 (3) | 129 |
C13—H13B···Cg4 | 0.98 | 2.67 | 3.583 (3) | 154 |
C12—H12C···Cg5 | 0.98 | 2.70 | 3.329 (3) | 121 |
C14—H14B···Cg5 | 0.98 | 2.76 | 3.354 (3) | 120 |
C12—H12B···Cg6 | 0.98 | 2.64 | 3.535 (3) | 151 |
C9—H9A···Cg6 | 0.99 | 2.75 | 3.655 (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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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.