organic compounds
[1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene]triiodoborane benzene hemisolvate
aInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de
In the title hemisolvate, C27H36BI3N2.0.5C6H6, the dihedral angles between the central heterocyclic ring and pendant benzene rings are 82.9 (8) and 88.7 (9)° and the complete benzene solvent molecule of crystallization is generated by a crystallographic centre of inversion. In the crystal, one very weak C—H⋯I interaction links the molecules into [001] chains.
Keywords: crystal structure; NHC; borane.
CCDC reference: 2012458
Structure description
NHC-complexed trihaloboranes BX3.NHCIPr (NHCIPr = IPr) are of great technological importance, because they find use in the synthesis of borsubhalides and also as precursor molecules for B=B double-bond-containing diborenes (Wang et al., 2007). In the course of our investigations of silanides (Lerner, 2005; Budanow et al., 2014), we treated trihalides of the type EX3 (E = B, Al, Ga; X = Cl, Br) with the NHC supersilyl silver complex [Ag(IPr)SitBu3] (Schödel et al., 2020). It is remarkable that along with tBu3SiEX2, EX3·IPr was thereby formed. The identity of EX3·IPr was confirmed by comparison with authentic samples that were obtained by an equimolar reaction of EX3 with NHCIPr (Schödel et al., 2020). We now describe the synthesis and structure of the NHC-complexed triiodoborane, BI3·IPr, which can be prepared by an analogous approach from NHCIPr and BI3, as shown in Fig. 1.
The molecular structure of the title compound (Fig. 2) does not show any unusual features: the C1—B1 bond length is 1.63 (2) Å and the dihedral angles between the central C1/C2/C3/N1/N2 heterocyclic ring and the pendant C11–C16 and C21–C26 benzene rings are 82.9 (8) and 88.7 (9)°, respectively. The complete benzene solvent molecule is generated by a crystallographic centre of inversion. The structures of the trifluoro-substituted borane (Bolte et al., 2020), which crystallizes without any solvent in the triclinic P, and that of the tribromo-substituted borane (Wang et al., 2007; Wang & Robinson, 2011), which crystallizes without any solvent in the monoclinic P21/n, agree well with that of the title compound.
The only directional interaction identified in the title compound is a very weak C—H⋯I interaction (Table 1), which links the molecules into C(6) [001] chains.
Synthesis and crystallization
The NHC-complexed triiodoborane (I) was synthesized according to a synthesis protocol for halogenated NHC-complexes (Schödel et al., 2020). Treatment of a mixture of BI3 (85 mg, 0.22 mmol) in 6 ml benzene/hexane with NHCIPr (IPr) (76 mg, 0.20 mmol) yielded quantitatively (I).
After pipetting from insoluble material, single crystals of (I) were grown from the reaction solution (benzene/hexane) at room temperature.
Refinement
Crystal data, data collection and structure . Some significant peaks remain in the final electron difference map close to the I atoms.
details are summarized in Table 2Structural data
CCDC reference: 2012458
https://doi.org/10.1107/S2414314620008639/hb4351sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620008639/hb4351Isup2.hkl
Data collection: X-AREA (Stoe & Cie, 2001); cell
X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).C27H36BI3N2·0.5C6H6 | F(000) = 1588 |
Mr = 819.14 | Dx = 1.662 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.0100 (14) Å | Cell parameters from 13397 reflections |
b = 12.5361 (11) Å | θ = 3.5–25.9° |
c = 16.3086 (18) Å | µ = 2.89 mm−1 |
β = 90.041 (8)° | T = 173 K |
V = 3273.2 (5) Å3 | Block, colourless |
Z = 4 | 0.21 × 0.18 × 0.18 mm |
STOE IPDS II two-circle- diffractometer | 4253 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.051 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (X-Area; Stoe & Cie, 2001) | h = −19→19 |
Tmin = 0.719, Tmax = 1.000 | k = −15→12 |
11917 measured reflections | l = −16→19 |
5990 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.094 | H-atom parameters constrained |
wR(F2) = 0.267 | w = 1/[σ2(Fo2) + (0.1189P)2 + 68.6175P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
5990 reflections | Δρmax = 6.06 e Å−3 |
325 parameters | Δρmin = −1.70 e Å−3 |
0 restraints |
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. The H atoms were refined using a riding model (C—H = 0.95–1.00 Å) and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl). |
x | y | z | Uiso*/Ueq | ||
B1 | 0.2324 (12) | 0.7430 (14) | 0.2487 (11) | 0.033 (4) | |
I1 | 0.12197 (7) | 0.67550 (9) | 0.18663 (6) | 0.0363 (3) | |
I2 | 0.25388 (8) | 0.90540 (9) | 0.19351 (6) | 0.0406 (3) | |
I3 | 0.34318 (8) | 0.63957 (11) | 0.21405 (7) | 0.0454 (4) | |
N1 | 0.1868 (8) | 0.6784 (9) | 0.3986 (7) | 0.028 (3) | |
N2 | 0.2796 (9) | 0.8040 (10) | 0.3982 (7) | 0.035 (3) | |
C1 | 0.2319 (9) | 0.7468 (11) | 0.3483 (8) | 0.025 (3) | |
C2 | 0.2103 (10) | 0.6921 (11) | 0.4788 (8) | 0.027 (3) | |
H2 | 0.189436 | 0.654241 | 0.524932 | 0.032* | |
C3 | 0.2693 (10) | 0.7701 (13) | 0.4796 (8) | 0.031 (3) | |
H3 | 0.298079 | 0.796690 | 0.526316 | 0.038* | |
C11 | 0.1170 (10) | 0.6030 (12) | 0.3801 (8) | 0.029 (3) | |
C12 | 0.1357 (10) | 0.4968 (12) | 0.3790 (9) | 0.034 (4) | |
C13 | 0.0698 (12) | 0.4282 (13) | 0.3723 (10) | 0.042 (4) | |
H13 | 0.080143 | 0.353572 | 0.371122 | 0.051* | |
C14 | −0.0126 (13) | 0.4652 (16) | 0.3671 (12) | 0.051 (5) | |
H14 | −0.057738 | 0.416627 | 0.361099 | 0.061* | |
C15 | −0.0266 (13) | 0.5719 (16) | 0.3709 (11) | 0.049 (5) | |
H15 | −0.082456 | 0.597269 | 0.368245 | 0.059* | |
C16 | 0.0370 (10) | 0.6443 (15) | 0.3785 (9) | 0.038 (4) | |
C17 | 0.2240 (12) | 0.4532 (14) | 0.3828 (12) | 0.046 (4) | |
H17 | 0.264021 | 0.514429 | 0.383612 | 0.055* | |
C18 | 0.0197 (11) | 0.7668 (13) | 0.3826 (9) | 0.036 (4) | |
H18 | 0.069516 | 0.804400 | 0.359575 | 0.043* | |
C21 | 0.3265 (10) | 0.9006 (13) | 0.3832 (9) | 0.032 (3) | |
C22 | 0.4127 (12) | 0.8955 (16) | 0.3719 (10) | 0.047 (4) | |
C23 | 0.4507 (14) | 0.992 (2) | 0.3564 (12) | 0.066 (7) | |
H23 | 0.508706 | 0.992851 | 0.343977 | 0.079* | |
C24 | 0.4077 (18) | 1.0863 (19) | 0.3581 (14) | 0.069 (6) | |
H24 | 0.435766 | 1.151592 | 0.347351 | 0.082* | |
C25 | 0.3235 (15) | 1.0863 (16) | 0.3755 (12) | 0.055 (5) | |
H25 | 0.294598 | 1.152424 | 0.376634 | 0.066* | |
C26 | 0.2808 (13) | 0.9963 (14) | 0.3908 (9) | 0.042 (4) | |
C27 | 0.4606 (13) | 0.7956 (17) | 0.3801 (11) | 0.052 (5) | |
H27 | 0.421405 | 0.733606 | 0.376851 | 0.062* | |
C28 | 0.1927 (13) | 0.9982 (14) | 0.4164 (11) | 0.046 (4) | |
H28 | 0.169521 | 0.924186 | 0.413065 | 0.055* | |
C171 | 0.2336 (16) | 0.3898 (18) | 0.4635 (13) | 0.064 (6) | |
H17A | 0.220421 | 0.436203 | 0.510040 | 0.095* | |
H17B | 0.195372 | 0.328798 | 0.463031 | 0.095* | |
H17C | 0.291254 | 0.364193 | 0.468496 | 0.095* | |
C172 | 0.2441 (15) | 0.3830 (14) | 0.3101 (13) | 0.056 (5) | |
H17D | 0.301550 | 0.356578 | 0.315018 | 0.084* | |
H17E | 0.205436 | 0.322448 | 0.308768 | 0.084* | |
H17F | 0.238512 | 0.424393 | 0.259455 | 0.084* | |
C181 | 0.0110 (14) | 0.7997 (16) | 0.4721 (12) | 0.053 (5) | |
H18A | 0.060730 | 0.777301 | 0.502604 | 0.080* | |
H18B | 0.005069 | 0.877349 | 0.475562 | 0.080* | |
H18C | −0.038561 | 0.765534 | 0.495714 | 0.080* | |
C182 | −0.0563 (12) | 0.7999 (18) | 0.3326 (12) | 0.054 (5) | |
H18D | −0.048754 | 0.777605 | 0.275433 | 0.082* | |
H18E | −0.106342 | 0.765724 | 0.355077 | 0.082* | |
H18F | −0.062712 | 0.877539 | 0.334926 | 0.082* | |
C271 | 0.5312 (15) | 0.782 (2) | 0.3144 (17) | 0.080 (8) | |
H27A | 0.506499 | 0.781796 | 0.259435 | 0.120* | |
H27B | 0.571259 | 0.840351 | 0.319159 | 0.120* | |
H27C | 0.560099 | 0.713624 | 0.323616 | 0.120* | |
C272 | 0.5046 (16) | 0.794 (2) | 0.4622 (17) | 0.081 (8) | |
H27D | 0.536418 | 0.727802 | 0.467732 | 0.122* | |
H27E | 0.542640 | 0.855189 | 0.465828 | 0.122* | |
H27F | 0.463099 | 0.798586 | 0.506255 | 0.122* | |
C281 | 0.1881 (16) | 1.0382 (18) | 0.5090 (11) | 0.062 (6) | |
H28A | 0.129747 | 1.039843 | 0.526916 | 0.093* | |
H28B | 0.219884 | 0.989359 | 0.544107 | 0.093* | |
H28C | 0.212028 | 1.109989 | 0.512931 | 0.093* | |
C282 | 0.1388 (14) | 1.0719 (16) | 0.3653 (11) | 0.053 (5) | |
H28D | 0.081148 | 1.069398 | 0.385329 | 0.079* | |
H28E | 0.160093 | 1.144959 | 0.369588 | 0.079* | |
H28F | 0.140292 | 1.049016 | 0.307829 | 0.079* | |
C31 | 0.4504 (16) | 0.514 (3) | 0.4308 (16) | 0.082 (8) | |
H31 | 0.416372 | 0.526785 | 0.384172 | 0.098* | |
C32 | 0.4206 (16) | 0.535 (2) | 0.5071 (19) | 0.084 (8) | |
H32 | 0.364101 | 0.557238 | 0.512498 | 0.101* | |
C33 | 0.4704 (15) | 0.526 (2) | 0.5791 (16) | 0.075 (7) | |
H33 | 0.449907 | 0.547160 | 0.631386 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.032 (10) | 0.033 (9) | 0.032 (9) | −0.008 (7) | 0.001 (7) | 0.009 (7) |
I1 | 0.0414 (6) | 0.0459 (6) | 0.0216 (5) | −0.0051 (5) | −0.0054 (4) | −0.0024 (4) |
I2 | 0.0556 (8) | 0.0415 (6) | 0.0247 (5) | −0.0091 (5) | −0.0036 (4) | 0.0046 (4) |
I3 | 0.0407 (7) | 0.0604 (8) | 0.0352 (6) | 0.0203 (6) | 0.0017 (5) | −0.0040 (5) |
N1 | 0.044 (8) | 0.023 (6) | 0.018 (6) | −0.007 (5) | 0.003 (5) | −0.010 (5) |
N2 | 0.054 (9) | 0.032 (7) | 0.020 (6) | 0.001 (6) | −0.002 (6) | 0.013 (5) |
C1 | 0.030 (8) | 0.024 (7) | 0.022 (7) | 0.005 (6) | 0.000 (6) | 0.000 (5) |
C2 | 0.037 (9) | 0.026 (7) | 0.017 (6) | 0.005 (6) | −0.011 (6) | −0.002 (5) |
C3 | 0.037 (9) | 0.041 (9) | 0.015 (6) | 0.003 (7) | −0.004 (6) | −0.006 (6) |
C11 | 0.037 (9) | 0.037 (8) | 0.014 (6) | −0.004 (7) | −0.005 (6) | 0.008 (6) |
C12 | 0.040 (9) | 0.027 (8) | 0.034 (8) | −0.003 (7) | −0.007 (7) | 0.011 (6) |
C13 | 0.057 (12) | 0.032 (9) | 0.038 (9) | −0.013 (8) | −0.010 (8) | −0.005 (7) |
C14 | 0.056 (13) | 0.050 (11) | 0.048 (11) | −0.019 (9) | −0.009 (9) | 0.000 (9) |
C15 | 0.051 (12) | 0.058 (12) | 0.038 (9) | −0.004 (9) | −0.003 (8) | −0.010 (8) |
C16 | 0.033 (9) | 0.058 (11) | 0.023 (7) | −0.006 (8) | 0.001 (6) | −0.003 (7) |
C17 | 0.047 (11) | 0.026 (8) | 0.065 (12) | 0.001 (8) | −0.007 (9) | 0.000 (8) |
C18 | 0.040 (10) | 0.040 (9) | 0.029 (8) | 0.000 (7) | −0.005 (7) | 0.005 (7) |
C21 | 0.037 (9) | 0.036 (8) | 0.021 (7) | −0.011 (7) | 0.000 (6) | 0.003 (6) |
C22 | 0.046 (11) | 0.064 (12) | 0.030 (8) | −0.008 (9) | −0.004 (8) | −0.007 (8) |
C23 | 0.053 (13) | 0.100 (19) | 0.046 (11) | −0.045 (13) | 0.004 (9) | 0.000 (11) |
C24 | 0.09 (2) | 0.047 (12) | 0.065 (14) | −0.018 (13) | −0.005 (13) | −0.001 (10) |
C25 | 0.077 (16) | 0.043 (11) | 0.046 (11) | −0.027 (10) | 0.000 (10) | −0.009 (8) |
C26 | 0.066 (12) | 0.038 (9) | 0.021 (7) | −0.005 (9) | −0.002 (7) | 0.000 (7) |
C27 | 0.050 (11) | 0.063 (13) | 0.042 (10) | −0.009 (10) | −0.015 (8) | −0.014 (9) |
C28 | 0.060 (13) | 0.027 (8) | 0.051 (10) | −0.010 (8) | 0.006 (9) | −0.008 (8) |
C171 | 0.076 (16) | 0.063 (14) | 0.051 (12) | 0.021 (12) | −0.017 (11) | 0.004 (10) |
C172 | 0.084 (16) | 0.030 (10) | 0.055 (12) | 0.004 (9) | 0.003 (11) | −0.001 (8) |
C181 | 0.062 (13) | 0.044 (11) | 0.054 (11) | 0.016 (9) | −0.002 (10) | −0.004 (9) |
C182 | 0.043 (11) | 0.075 (14) | 0.046 (10) | 0.011 (10) | −0.009 (9) | −0.006 (10) |
C271 | 0.047 (14) | 0.11 (2) | 0.086 (18) | 0.002 (14) | 0.019 (12) | −0.016 (16) |
C272 | 0.065 (16) | 0.087 (19) | 0.093 (19) | 0.011 (14) | −0.012 (14) | −0.030 (15) |
C281 | 0.095 (18) | 0.056 (13) | 0.035 (10) | 0.025 (12) | 0.012 (10) | −0.002 (9) |
C282 | 0.074 (14) | 0.051 (11) | 0.033 (9) | 0.007 (10) | 0.000 (9) | 0.006 (8) |
C31 | 0.059 (15) | 0.12 (2) | 0.063 (15) | 0.023 (15) | −0.017 (12) | −0.002 (15) |
C32 | 0.045 (13) | 0.10 (2) | 0.10 (2) | 0.016 (13) | −0.012 (14) | 0.015 (17) |
C33 | 0.046 (13) | 0.11 (2) | 0.068 (15) | −0.002 (13) | 0.001 (11) | −0.011 (14) |
B1—C1 | 1.63 (2) | C25—H25 | 0.9500 |
B1—I1 | 2.205 (18) | C26—C28 | 1.47 (3) |
B1—I2 | 2.252 (17) | C27—C272 | 1.51 (3) |
B1—I3 | 2.27 (2) | C27—C271 | 1.57 (3) |
N1—C2 | 1.373 (17) | C27—H27 | 1.0000 |
N1—C1 | 1.389 (19) | C28—C282 | 1.51 (3) |
N1—C11 | 1.494 (19) | C28—C281 | 1.59 (3) |
N2—C1 | 1.326 (19) | C28—H28 | 1.0000 |
N2—C3 | 1.404 (18) | C171—H17A | 0.9800 |
N2—C21 | 1.45 (2) | C171—H17B | 0.9800 |
C2—C3 | 1.36 (2) | C171—H17C | 0.9800 |
C2—H2 | 0.9500 | C172—H17D | 0.9800 |
C3—H3 | 0.9500 | C172—H17E | 0.9800 |
C11—C12 | 1.37 (2) | C172—H17F | 0.9800 |
C11—C16 | 1.38 (2) | C181—H18A | 0.9800 |
C12—C13 | 1.37 (2) | C181—H18B | 0.9800 |
C12—C17 | 1.52 (2) | C181—H18C | 0.9800 |
C13—C14 | 1.40 (3) | C182—H18D | 0.9800 |
C13—H13 | 0.9500 | C182—H18E | 0.9800 |
C14—C15 | 1.36 (3) | C182—H18F | 0.9800 |
C14—H14 | 0.9500 | C271—H27A | 0.9800 |
C15—C16 | 1.37 (3) | C271—H27B | 0.9800 |
C15—H15 | 0.9500 | C271—H27C | 0.9800 |
C16—C18 | 1.56 (2) | C272—H27D | 0.9800 |
C17—C172 | 1.51 (3) | C272—H27E | 0.9800 |
C17—C171 | 1.54 (3) | C272—H27F | 0.9800 |
C17—H17 | 1.0000 | C281—H28A | 0.9800 |
C18—C182 | 1.52 (2) | C281—H28B | 0.9800 |
C18—C181 | 1.52 (2) | C281—H28C | 0.9800 |
C18—H18 | 1.0000 | C282—H28D | 0.9800 |
C21—C22 | 1.39 (3) | C282—H28E | 0.9800 |
C21—C26 | 1.41 (2) | C282—H28F | 0.9800 |
C22—C23 | 1.38 (3) | C31—C32 | 1.36 (4) |
C22—C27 | 1.47 (3) | C31—C33i | 1.37 (3) |
C23—C24 | 1.37 (4) | C31—H31 | 0.9500 |
C23—H23 | 0.9500 | C32—C33 | 1.42 (3) |
C24—C25 | 1.38 (3) | C32—H32 | 0.9500 |
C24—H24 | 0.9500 | C33—H33 | 0.9500 |
C25—C26 | 1.34 (3) | ||
C1—B1—I1 | 117.7 (11) | C272—C27—C22 | 109.4 (17) |
C1—B1—I2 | 112.0 (11) | C272—C27—C271 | 105.5 (19) |
I1—B1—I2 | 106.6 (7) | C22—C27—C271 | 114 (2) |
C1—B1—I3 | 105.6 (10) | C272—C27—H27 | 109.2 |
I1—B1—I3 | 107.0 (8) | C22—C27—H27 | 109.2 |
I2—B1—I3 | 107.3 (7) | C271—C27—H27 | 109.2 |
C2—N1—C1 | 110.1 (12) | C26—C28—C282 | 113.6 (16) |
C2—N1—C11 | 118.4 (12) | C26—C28—C281 | 108.5 (16) |
C1—N1—C11 | 131.3 (11) | C282—C28—C281 | 107.7 (16) |
C1—N2—C3 | 110.5 (13) | C26—C28—H28 | 109.0 |
C1—N2—C21 | 130.4 (12) | C282—C28—H28 | 109.0 |
C3—N2—C21 | 118.3 (12) | C281—C28—H28 | 109.0 |
N2—C1—N1 | 105.7 (12) | C17—C171—H17A | 109.5 |
N2—C1—B1 | 128.7 (14) | C17—C171—H17B | 109.5 |
N1—C1—B1 | 125.1 (12) | H17A—C171—H17B | 109.5 |
C3—C2—N1 | 106.8 (13) | C17—C171—H17C | 109.5 |
C3—C2—H2 | 126.6 | H17A—C171—H17C | 109.5 |
N1—C2—H2 | 126.6 | H17B—C171—H17C | 109.5 |
C2—C3—N2 | 106.8 (12) | C17—C172—H17D | 109.5 |
C2—C3—H3 | 126.6 | C17—C172—H17E | 109.5 |
N2—C3—H3 | 126.6 | H17D—C172—H17E | 109.5 |
C12—C11—C16 | 124.7 (15) | C17—C172—H17F | 109.5 |
C12—C11—N1 | 117.1 (14) | H17D—C172—H17F | 109.5 |
C16—C11—N1 | 117.4 (14) | H17E—C172—H17F | 109.5 |
C11—C12—C13 | 116.5 (16) | C18—C181—H18A | 109.5 |
C11—C12—C17 | 123.8 (15) | C18—C181—H18B | 109.5 |
C13—C12—C17 | 119.7 (15) | H18A—C181—H18B | 109.5 |
C12—C13—C14 | 121.6 (16) | C18—C181—H18C | 109.5 |
C12—C13—H13 | 119.2 | H18A—C181—H18C | 109.5 |
C14—C13—H13 | 119.2 | H18B—C181—H18C | 109.5 |
C15—C14—C13 | 118.6 (18) | C18—C182—H18D | 109.5 |
C15—C14—H14 | 120.7 | C18—C182—H18E | 109.5 |
C13—C14—H14 | 120.7 | H18D—C182—H18E | 109.5 |
C16—C15—C14 | 122 (2) | C18—C182—H18F | 109.5 |
C16—C15—H15 | 118.9 | H18D—C182—H18F | 109.5 |
C14—C15—H15 | 118.9 | H18E—C182—H18F | 109.5 |
C15—C16—C11 | 116.3 (17) | C27—C271—H27A | 109.5 |
C15—C16—C18 | 121.6 (16) | C27—C271—H27B | 109.5 |
C11—C16—C18 | 122.1 (15) | H27A—C271—H27B | 109.5 |
C172—C17—C12 | 112.2 (16) | C27—C271—H27C | 109.5 |
C172—C17—C171 | 110.3 (15) | H27A—C271—H27C | 109.5 |
C12—C17—C171 | 108.2 (17) | H27B—C271—H27C | 109.5 |
C172—C17—H17 | 108.7 | C27—C272—H27D | 109.5 |
C12—C17—H17 | 108.7 | C27—C272—H27E | 109.5 |
C171—C17—H17 | 108.7 | H27D—C272—H27E | 109.5 |
C182—C18—C181 | 111.5 (16) | C27—C272—H27F | 109.5 |
C182—C18—C16 | 112.7 (15) | H27D—C272—H27F | 109.5 |
C181—C18—C16 | 108.9 (13) | H27E—C272—H27F | 109.5 |
C182—C18—H18 | 107.9 | C28—C281—H28A | 109.5 |
C181—C18—H18 | 107.9 | C28—C281—H28B | 109.5 |
C16—C18—H18 | 107.9 | H28A—C281—H28B | 109.5 |
C22—C21—C26 | 124.4 (16) | C28—C281—H28C | 109.5 |
C22—C21—N2 | 119.9 (16) | H28A—C281—H28C | 109.5 |
C26—C21—N2 | 115.3 (15) | H28B—C281—H28C | 109.5 |
C21—C22—C23 | 115 (2) | C28—C282—H28D | 109.5 |
C21—C22—C27 | 122.8 (18) | C28—C282—H28E | 109.5 |
C23—C22—C27 | 122 (2) | H28D—C282—H28E | 109.5 |
C24—C23—C22 | 122 (2) | C28—C282—H28F | 109.5 |
C24—C23—H23 | 118.9 | H28D—C282—H28F | 109.5 |
C22—C23—H23 | 118.9 | H28E—C282—H28F | 109.5 |
C23—C24—C25 | 120 (2) | C32—C31—C33i | 120 (2) |
C23—C24—H24 | 120.1 | C32—C31—H31 | 119.8 |
C25—C24—H24 | 120.1 | C33i—C31—H31 | 119.8 |
C26—C25—C24 | 123 (2) | C31—C32—C33 | 123 (2) |
C26—C25—H25 | 118.7 | C31—C32—H32 | 118.6 |
C24—C25—H25 | 118.7 | C33—C32—H32 | 118.6 |
C25—C26—C21 | 115.7 (19) | C31i—C33—C32 | 117 (2) |
C25—C26—C28 | 121.9 (18) | C31i—C33—H33 | 121.7 |
C21—C26—C28 | 122.4 (15) | C32—C33—H33 | 121.7 |
C3—N2—C1—N1 | 3.0 (17) | C11—C12—C17—C172 | −122.6 (18) |
C21—N2—C1—N1 | −166.1 (16) | C13—C12—C17—C172 | 56 (2) |
C3—N2—C1—B1 | −169.6 (15) | C11—C12—C17—C171 | 115.4 (18) |
C21—N2—C1—B1 | 21 (3) | C13—C12—C17—C171 | −66 (2) |
C2—N1—C1—N2 | −2.5 (17) | C15—C16—C18—C182 | −32 (2) |
C11—N1—C1—N2 | 172.8 (14) | C11—C16—C18—C182 | 145.9 (16) |
C2—N1—C1—B1 | 170.5 (14) | C15—C16—C18—C181 | 91.9 (19) |
C11—N1—C1—B1 | −14 (2) | C11—C16—C18—C181 | −89.8 (19) |
I1—B1—C1—N2 | −162.7 (13) | C1—N2—C21—C22 | −102 (2) |
I2—B1—C1—N2 | −39 (2) | C3—N2—C21—C22 | 89.3 (18) |
I3—B1—C1—N2 | 77.9 (17) | C1—N2—C21—C26 | 85 (2) |
I1—B1—C1—N1 | 26 (2) | C3—N2—C21—C26 | −83.5 (18) |
I2—B1—C1—N1 | 150.2 (12) | C26—C21—C22—C23 | −9 (2) |
I3—B1—C1—N1 | −93.3 (15) | N2—C21—C22—C23 | 178.6 (15) |
C1—N1—C2—C3 | 0.9 (17) | C26—C21—C22—C27 | 167.8 (15) |
C11—N1—C2—C3 | −175.0 (13) | N2—C21—C22—C27 | −4 (2) |
N1—C2—C3—N2 | 0.9 (17) | C21—C22—C23—C24 | 5 (3) |
C1—N2—C3—C2 | −2.5 (18) | C27—C22—C23—C24 | −172.3 (19) |
C21—N2—C3—C2 | 168.1 (14) | C22—C23—C24—C25 | 0 (3) |
C2—N1—C11—C12 | −79.4 (18) | C23—C24—C25—C26 | 0 (3) |
C1—N1—C11—C12 | 105.6 (18) | C24—C25—C26—C21 | −4 (3) |
C2—N1—C11—C16 | 90.4 (16) | C24—C25—C26—C28 | 174.6 (19) |
C1—N1—C11—C16 | −84.6 (19) | C22—C21—C26—C25 | 9 (2) |
C16—C11—C12—C13 | 3 (2) | N2—C21—C26—C25 | −178.7 (14) |
N1—C11—C12—C13 | 172.0 (13) | C22—C21—C26—C28 | −169.4 (16) |
C16—C11—C12—C17 | −178.5 (15) | N2—C21—C26—C28 | 3 (2) |
N1—C11—C12—C17 | −9 (2) | C21—C22—C27—C272 | −102 (2) |
C11—C12—C13—C14 | 0 (2) | C23—C22—C27—C272 | 75 (3) |
C17—C12—C13—C14 | −178.8 (17) | C21—C22—C27—C271 | 140.1 (18) |
C12—C13—C14—C15 | −2 (3) | C23—C22—C27—C271 | −43 (2) |
C13—C14—C15—C16 | 1 (3) | C25—C26—C28—C282 | 46 (2) |
C14—C15—C16—C11 | 2 (3) | C21—C26—C28—C282 | −135.5 (16) |
C14—C15—C16—C18 | 179.9 (17) | C25—C26—C28—C281 | −73 (2) |
C12—C11—C16—C15 | −4 (2) | C21—C26—C28—C281 | 104.9 (17) |
N1—C11—C16—C15 | −172.7 (13) | C33i—C31—C32—C33 | 5 (5) |
C12—C11—C16—C18 | 178.0 (14) | C31—C32—C33—C31i | −5 (5) |
N1—C11—C16—C18 | 9 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···I2ii | 0.95 | 3.03 | 3.773 (13) | 136 |
Symmetry code: (ii) x, −y+3/2, z+1/2. |
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