research communications
Two salts of the 6,6-difluoro-6H-dibenzo[c,e][1,2]oxaborinin-6-ide anion with different cations
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
The crystal structures are reported of the 6,6-difluoro-6H-dibenzo[c,e][1,2]oxaborinin-6-ide (or 9,9-difluoro-10-oxa-9-boraphenanthren-9-ide) anion with two different cations, namely, potassium 6,6-difluoro-6H-dibenzo[c,e][1,2]oxaborinin-6-ide, K+·C12H8BF2O−, (II), featuring a polymeric structure, and bis(tetraphenylphosphonium) bis(6,6-difluoro-6H-dibenzo[c,e][1,2]oxaborinin-6-ide) acetonitrile trisolvate, 2C24H20P+·2C12H8BF2O−·3CH3CN, (III), which is composed of discrete cations, anions and acetonitrile solvent molecules linked by C—H⋯O, C—H⋯N and C—H⋯F hydrogen bonds. There are only minor differences in the geometrical parameters of the anions in these structures.
Keywords: crystal structure; boron; fluorine; potassium.
1. Chemical context
Oxaboraphenanthrenes are interesting building blocks for organic optoelectronic materials. Recently, we have prepared various 9-substituted oxaboraphenanthrene derivatives and investigated their stability and luminescence behavior (Budanow et al., 2016). The starting material for our approach was 9-chloro-10,9-oxaboraphenanthrene (Budanow et al., 2014), which is, however, an air-sensitive compound. Therefore we were now interested in air-stable precursors for oxaboraphenanthrene preparation.
Because certain 2, we tested whether (I) (Fig. 1) could be transformed into a fluoroborane upon treatment with KHF2. Indeed, by stirring a solution of (I) in the presence of KHF2 in methanol, a clean and quantitative OH/F exchange was established and 9,9-difluorido-10,9-oxaboraphenanthrene potassium (II) was obtained (Fig. 1). Subsequent treatment of (II) with Ph4PBr gave the 9,9-difluorido-10,9-oxaboraphenanthrene salt as an acetonitrile solvate (III). The crystal structures of (II) and (III) are now described.
are readily fluorinated with KHF2. Structural commentary
The anion in (II) has an almost planar skeleton (r.m.s. deviation 0.103 Å for the C, B and O atoms) (Fig. 2) and the bond lengths of the B and O atoms are in their usual ranges [B1—C1 = 1.591 (2); B1—O1 = 1.4564 (19), C11—O1 = 1.3678 (17) Å]. The B atom is substituted by two F ligands with bond lengths B1—F1 = 1.4483 (18) and B1—F2 = 1.4325 (18) Å. The dihedral angle between the C1–C6 and C11–C16 aromatic rings in the anion of (II) is 11.09 (9) Å.
The III) consists of two C12H8BF2O− anions (Figs. 3 and 4), two C24H20P+ tetraphenylphosphonium cations and three acetonitrile solvent molecules, one of which is disordered over two sets of sites. The oxaboraphenanthrene moieties of both the B1 and B1A anions are again essentially planar (r.m.s. deviations = 0.042 and 0.093 Å, respectively). The bond lengths involving B and O [B1—C1 = 1.603 (2); B1—O1 = 1.466 (2); B1—F1 = 1.412 (2); B1—F2 = 1.411 (2), C11—O1 = 1.3492 (19) Å and B1A—C1A = 1.601 (2), B1A—O1A = 1.475 (2); B1A—F1A = 1.417 (2); B1A—F2A = 1.415 (2); C11A—O1A = 1.3435 (19) Å] show some slight variations between (II) and (III). In (II), the B—F bonds are longer than in (III), which is presumably due to the F⋯K contacts.
of (3. Supramolecular features
The extended structure of (II) features a polymeric network forming layers lying parallel to (001) (Figs. 5, 6). K1 is bonded to four F atoms with K—F distances ranging from 2.6132 (9) to 2.7407 (10) Å and two O atoms with K—O distances of 2.7307 (10) and 2.9324 (11) Å. There is one relatively short K⋯C contact [K1⋯C11 = 3.3883 (14)Å] but there are no K⋯π interactions.
In the extended structure of (III) (Fig. 7), the component species are linked by numerous C—H⋯O, C—H⋯N and C—H⋯F interactions (Table 1) into a three-dimensional network.
4. Database survey
There are no structures in the Cambridge Structural Database (version 5.41 of November 2019 plus three updates; Groom et al., 2016) containing the 6,6′-difluoro-6H-dibenzo[c,e][1,2]oxaborinine anion. When the F ligands in the query are changed to any ligand, three structures are found, namely (6H-dibenzo[c,e][1,2]oxadihydridoborato-O)(tetrahydrofuran)(tetramethylethylenediamine)lithium (CSD refcode CADVIN; Knizek & Nöth, 2000), [6-phenyl-6-(phenyl)-6H-6-dibenzo[c,e][1,2]oxaborinine]bis(tetrahydrofuran)lithium benzene solvate (TUZTAL; Budanow et al., 2016) and (9-tert-butyl-9H-9-benzo[c][1,2]benzoxaborinino[4,3,2-ij][2,1]benzoxaborinine)bis(tetrahydrofuran)lithium (9-tert-butyl-9H-9-benzo[c][1,2]benzoxaborinino[4,3,2-ij][2,1]benzoxaborinine)tris(tetrahydrofuran)lithium (RUHZUS; Sato et al., 2020). Since in RUHZUS, the ligands at B are involved in a ring closure, this structure is excluded from the comparison with (II) and (III).
The bond lengths involving B and O in these structures are: CADVIN: B—C = 1.589, B—O = 1.534, C—O = 1.360 Å; TUZTAL: B—C = 1.611, B—O = 1.543, C—O = 1.358 Å. Whereas the B—C and the O—C bonds are in the same range as in (II) and (III), the B—O bond is significantly longer than in (II) and (III). It is notable that the oxaboraphenanthrene moieties in CADVIN and TUZTAL are far more distorted from planarity than in (II) and (III): the dihedral angles between the aromatic rings are 16.9° in CADVIN and 19.1° in TUZTAL. These dihedral angles are 11.09 (9)° in (II) and 4.53 (7) and 9.68 (8)° in (III).
5. Synthesis and crystallization
Synthesis of 9,9-difluorido-10,9-oxaboraphenanthrene potassium (II):
To a solution of 9-hydroxooxaboraphenanthrene (I) (1.556 g, 7.94 mmol) in methanol (70 ml) a solution of KHF2 (2.669 g, 34.17 mmol) in methanol (30 ml) and water (30 ml) was added at room temperature and the resulting reacting mixture was stirred for 12 h. After removal of all volatiles in vacuo, the residue was extracted into acetonitrile (30 ml). The colorless suspension was filtered. All volatiles were removed in vacuo. The product was obtained as a colorless powder in a yield of 66% (1.34 g, 5.23 mmol). Slow evaporation of a saturated acetonitrile solution of (II) over Granopent led to colorless plates, which were suitable for an investigation by X-ray crystallography.
Synthesis of 9,9-difluorido-10,9-oxaboraphenanthrene tetraphenylphosphonium (III):
To a solution of (II) (0.511 g, 2.0 mmol) in acetonitrile (25 ml) Ph4PBr (0.88 g, 2.10 mmol) was added at room temperature and the resulting reacting mixture was stirred for 12 h. The colorless suspension was filtered. After removal of all volatiles, the product was obtained as a colorless powder in a yield of 92% (0.221 g, 0.36 mmol). Slow evaporation of a saturated acetonitrile solution of (III) over Granopent led to colorless blocks, which were suitable for an investigation by X-ray crystallography.
6. Refinement
Crystal data, data collection and structure . The H atoms for both structures were refined using a riding model with C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C) or with Cmethyl—H = 0.98 Å and with Uiso(H) = 1.5Ueq(C). The methyl groups were allowed to rotate but not to tip. In (III), the C≡N group of one acetonitrile molecule is disordered over two sets of sites with a site occupation factor of 0.545 (5) for the major disorder component.
details are summarized in Table 2
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Supporting information
https://doi.org/10.1107/S2056989020015066/hb7952sup1.cif
contains datablocks II, III, global. DOI:Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020015066/hb7952IIsup2.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989020015066/hb7952IIIsup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020015066/hb7952IIsup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020015066/hb7952IIIsup5.cml
For both structures, 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: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2015b) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).K+·C12H8BF2O− | F(000) = 520 |
Mr = 256.09 | Dx = 1.601 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.2962 (10) Å | Cell parameters from 6730 reflections |
b = 6.2300 (4) Å | θ = 3.6–26.0° |
c = 12.9294 (11) Å | µ = 0.50 mm−1 |
β = 97.226 (6)° | T = 173 K |
V = 1062.50 (14) Å3 | Plate, colourless |
Z = 4 | 0.48 × 0.46 × 0.23 mm |
STOE IPDS II two-circle diffractometer | 1796 reflections with I > 2σ(I) |
ω scans | Rint = 0.050 |
Absorption correction: multi-scan (X-Area; Stoe & Cie, 2001) | θmax = 25.6°, θmin = 3.6° |
Tmin = 0.794, Tmax = 0.893 | h = −16→16 |
6459 measured reflections | k = −7→7 |
1980 independent reflections | l = −15→13 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1783P] where P = (Fo2 + 2Fc2)/3 |
1980 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
K1 | 0.47144 (2) | 0.77289 (5) | 0.38440 (2) | 0.02252 (13) | |
B1 | 0.61842 (12) | 0.3281 (3) | 0.38931 (12) | 0.0182 (3) | |
O1 | 0.62336 (7) | 0.46771 (16) | 0.48017 (7) | 0.0201 (2) | |
F1 | 0.55034 (6) | 0.42677 (15) | 0.30658 (6) | 0.0258 (2) | |
F2 | 0.56553 (6) | 0.13979 (14) | 0.41608 (7) | 0.0246 (2) | |
C1 | 0.72587 (11) | 0.2796 (2) | 0.35252 (11) | 0.0186 (3) | |
C2 | 0.80729 (11) | 0.4170 (2) | 0.38571 (11) | 0.0195 (3) | |
C3 | 0.90255 (11) | 0.3756 (3) | 0.35387 (12) | 0.0249 (3) | |
H3 | 0.958382 | 0.465504 | 0.377711 | 0.030* | |
C4 | 0.91617 (12) | 0.2057 (3) | 0.28830 (13) | 0.0279 (4) | |
H4 | 0.980868 | 0.181458 | 0.266586 | 0.034* | |
C5 | 0.83640 (12) | 0.0709 (3) | 0.25411 (12) | 0.0271 (3) | |
H5 | 0.845540 | −0.044942 | 0.208452 | 0.033* | |
C6 | 0.74217 (12) | 0.1076 (3) | 0.28767 (11) | 0.0226 (3) | |
H6 | 0.687666 | 0.012800 | 0.265759 | 0.027* | |
C11 | 0.70096 (11) | 0.6112 (2) | 0.50227 (11) | 0.0177 (3) | |
C12 | 0.79123 (11) | 0.5970 (2) | 0.45628 (11) | 0.0194 (3) | |
C13 | 0.86343 (12) | 0.7582 (2) | 0.48232 (13) | 0.0253 (3) | |
H13 | 0.924129 | 0.756567 | 0.450636 | 0.030* | |
C14 | 0.84952 (12) | 0.9195 (3) | 0.55239 (13) | 0.0285 (4) | |
H14 | 0.899937 | 1.026782 | 0.567981 | 0.034* | |
C15 | 0.76149 (12) | 0.9244 (2) | 0.60003 (12) | 0.0263 (3) | |
H15 | 0.752271 | 1.032398 | 0.649848 | 0.032* | |
C16 | 0.68731 (12) | 0.7707 (2) | 0.57435 (12) | 0.0221 (3) | |
H16 | 0.626722 | 0.774242 | 0.606210 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
K1 | 0.0320 (2) | 0.01629 (19) | 0.01999 (19) | −0.00165 (13) | 0.00615 (13) | 0.00069 (11) |
B1 | 0.0191 (7) | 0.0158 (7) | 0.0197 (7) | −0.0023 (6) | 0.0025 (6) | −0.0009 (6) |
O1 | 0.0187 (5) | 0.0208 (5) | 0.0215 (5) | −0.0053 (4) | 0.0048 (4) | −0.0038 (4) |
F1 | 0.0269 (5) | 0.0275 (5) | 0.0218 (4) | 0.0072 (4) | −0.0016 (3) | −0.0030 (3) |
F2 | 0.0244 (4) | 0.0189 (4) | 0.0317 (5) | −0.0070 (4) | 0.0085 (3) | −0.0034 (4) |
C1 | 0.0210 (7) | 0.0182 (7) | 0.0166 (6) | 0.0005 (6) | 0.0028 (5) | 0.0031 (5) |
C2 | 0.0200 (7) | 0.0206 (7) | 0.0181 (6) | 0.0001 (6) | 0.0032 (5) | 0.0038 (6) |
C3 | 0.0197 (7) | 0.0289 (8) | 0.0266 (7) | −0.0015 (6) | 0.0052 (6) | 0.0014 (6) |
C4 | 0.0222 (8) | 0.0355 (9) | 0.0275 (8) | 0.0053 (7) | 0.0084 (6) | 0.0002 (7) |
C5 | 0.0310 (8) | 0.0262 (8) | 0.0249 (7) | 0.0066 (7) | 0.0062 (6) | −0.0024 (6) |
C6 | 0.0235 (7) | 0.0212 (7) | 0.0231 (7) | −0.0004 (6) | 0.0029 (6) | −0.0001 (6) |
C11 | 0.0174 (6) | 0.0159 (6) | 0.0188 (6) | −0.0017 (6) | −0.0013 (5) | 0.0022 (5) |
C12 | 0.0201 (7) | 0.0191 (7) | 0.0184 (6) | −0.0013 (6) | 0.0002 (5) | 0.0031 (5) |
C13 | 0.0215 (7) | 0.0253 (8) | 0.0290 (8) | −0.0054 (6) | 0.0028 (6) | 0.0018 (6) |
C14 | 0.0285 (8) | 0.0217 (8) | 0.0335 (8) | −0.0077 (7) | −0.0028 (6) | −0.0018 (6) |
C15 | 0.0295 (8) | 0.0189 (7) | 0.0286 (8) | 0.0013 (6) | −0.0038 (6) | −0.0037 (6) |
C16 | 0.0224 (7) | 0.0211 (7) | 0.0222 (7) | 0.0031 (6) | 0.0002 (6) | −0.0008 (6) |
K1—F2i | 2.6132 (9) | C2—C3 | 1.404 (2) |
K1—F1ii | 2.6307 (9) | C2—C12 | 1.478 (2) |
K1—F1 | 2.6511 (9) | C3—C4 | 1.382 (2) |
K1—O1iii | 2.7307 (10) | C3—H3 | 0.9500 |
K1—F2iii | 2.7407 (10) | C4—C5 | 1.381 (2) |
K1—O1 | 2.9324 (11) | C4—H4 | 0.9500 |
K1—B1iii | 3.3560 (16) | C5—C6 | 1.395 (2) |
K1—B1 | 3.3867 (17) | C5—H5 | 0.9500 |
K1—C11 | 3.3883 (14) | C6—H6 | 0.9500 |
K1—C6ii | 3.5338 (16) | C11—C16 | 1.390 (2) |
K1—C16 | 3.5351 (15) | C11—C12 | 1.408 (2) |
K1—K1iv | 4.1169 (6) | C12—C13 | 1.401 (2) |
B1—F2 | 1.4325 (18) | C13—C14 | 1.381 (2) |
B1—F1 | 1.4483 (18) | C13—H13 | 0.9500 |
B1—O1 | 1.4564 (19) | C14—C15 | 1.390 (2) |
B1—C1 | 1.591 (2) | C14—H14 | 0.9500 |
O1—C11 | 1.3678 (17) | C15—C16 | 1.385 (2) |
C1—C6 | 1.395 (2) | C15—H15 | 0.9500 |
C1—C2 | 1.404 (2) | C16—H16 | 0.9500 |
F2i—K1—F1ii | 79.77 (3) | F2—B1—C1 | 113.79 (12) |
F2i—K1—F1 | 124.50 (3) | F1—B1—C1 | 111.18 (12) |
F1ii—K1—F1 | 86.689 (19) | O1—B1—C1 | 113.80 (12) |
F2i—K1—O1iii | 129.06 (3) | F2—B1—K1iii | 52.87 (6) |
F1ii—K1—O1iii | 142.82 (3) | F1—B1—K1iii | 117.74 (9) |
F1—K1—O1iii | 91.92 (3) | O1—B1—K1iii | 52.67 (6) |
F2i—K1—F2iii | 79.51 (3) | C1—B1—K1iii | 131.05 (9) |
F1ii—K1—F2iii | 143.09 (3) | F2—B1—K1 | 112.03 (9) |
F1—K1—F2iii | 130.17 (3) | F1—B1—K1 | 48.20 (6) |
O1iii—K1—F2iii | 49.72 (3) | O1—B1—K1 | 59.60 (7) |
F2i—K1—O1 | 102.13 (3) | C1—B1—K1 | 133.45 (9) |
F1ii—K1—O1 | 128.41 (3) | K1iii—B1—K1 | 84.37 (4) |
F1—K1—O1 | 49.34 (3) | C11—O1—B1 | 121.00 (11) |
O1iii—K1—O1 | 73.88 (3) | C11—O1—K1iii | 128.44 (8) |
F2iii—K1—O1 | 85.80 (3) | B1—O1—K1iii | 102.23 (8) |
F2i—K1—B1iii | 104.08 (3) | C11—O1—K1 | 97.24 (8) |
F1ii—K1—B1iii | 151.33 (4) | B1—O1—K1 | 95.03 (8) |
F1—K1—B1iii | 112.31 (4) | K1iii—O1—K1 | 106.12 (3) |
O1iii—K1—B1iii | 25.09 (3) | B1—F1—K1v | 121.56 (8) |
F2iii—K1—B1iii | 24.63 (3) | B1—F1—K1 | 107.77 (8) |
O1—K1—B1iii | 79.17 (3) | K1v—F1—K1 | 130.59 (3) |
F2i—K1—B1 | 116.68 (4) | B1—F2—K1vi | 156.70 (8) |
F1ii—K1—B1 | 108.11 (4) | B1—F2—K1iii | 102.50 (8) |
F1—K1—B1 | 24.03 (3) | K1vi—F2—K1iii | 100.49 (3) |
O1iii—K1—B1 | 81.41 (4) | C6—C1—C2 | 118.68 (13) |
F2iii—K1—B1 | 108.43 (3) | C6—C1—B1 | 122.63 (13) |
O1—K1—B1 | 25.37 (3) | C2—C1—B1 | 118.69 (13) |
B1iii—K1—B1 | 95.63 (4) | C1—C2—C3 | 119.20 (14) |
F2i—K1—C11 | 78.65 (3) | C1—C2—C12 | 119.03 (13) |
F1ii—K1—C11 | 121.14 (3) | C3—C2—C12 | 121.73 (14) |
F1—K1—C11 | 63.37 (3) | C4—C3—C2 | 120.87 (15) |
O1iii—K1—C11 | 90.61 (3) | C4—C3—H3 | 119.6 |
F2iii—K1—C11 | 83.90 (3) | C2—C3—H3 | 119.6 |
O1—K1—C11 | 23.61 (3) | C5—C4—C3 | 120.48 (14) |
B1iii—K1—C11 | 87.21 (4) | C5—C4—H4 | 119.8 |
B1—K1—C11 | 42.55 (4) | C3—C4—H4 | 119.8 |
F2i—K1—C6ii | 133.20 (3) | C4—C5—C6 | 118.98 (14) |
F1ii—K1—C6ii | 61.99 (3) | C4—C5—H5 | 120.5 |
F1—K1—C6ii | 81.32 (3) | C6—C5—H5 | 120.5 |
O1iii—K1—C6ii | 81.05 (3) | C1—C6—C5 | 121.75 (15) |
F2iii—K1—C6ii | 115.17 (3) | C1—C6—K1v | 88.92 (9) |
O1—K1—C6ii | 122.23 (3) | C5—C6—K1v | 122.27 (10) |
B1iii—K1—C6ii | 98.52 (4) | C1—C6—H6 | 119.1 |
B1—K1—C6ii | 100.93 (4) | C5—C6—H6 | 119.1 |
C11—K1—C6ii | 143.48 (4) | K1v—C6—H6 | 58.0 |
F2i—K1—C16 | 64.13 (3) | O1—C11—C16 | 116.65 (13) |
F1ii—K1—C16 | 129.60 (3) | O1—C11—C12 | 122.12 (13) |
F1—K1—C16 | 86.27 (3) | C16—C11—C12 | 121.22 (14) |
O1iii—K1—C16 | 87.27 (3) | O1—C11—K1 | 59.16 (6) |
F2iii—K1—C16 | 64.72 (3) | C16—C11—K1 | 84.42 (9) |
O1—K1—C16 | 41.25 (3) | C12—C11—K1 | 126.61 (9) |
B1iii—K1—C16 | 74.96 (4) | C13—C12—C11 | 116.64 (14) |
B1—K1—C16 | 64.38 (4) | C13—C12—C2 | 123.00 (13) |
C11—K1—C16 | 23.03 (3) | C11—C12—C2 | 120.35 (13) |
C6ii—K1—C16 | 162.61 (4) | C14—C13—C12 | 122.36 (15) |
F2i—K1—K1iv | 40.89 (2) | C14—C13—H13 | 118.8 |
F1ii—K1—K1iv | 114.80 (2) | C12—C13—H13 | 118.8 |
F1—K1—K1iv | 142.09 (2) | C13—C14—C15 | 119.76 (15) |
O1iii—K1—K1iv | 88.26 (2) | C13—C14—H14 | 120.1 |
F2iii—K1—K1iv | 38.619 (19) | C15—C14—H14 | 120.1 |
O1—K1—K1iv | 94.86 (2) | C16—C15—C14 | 119.52 (14) |
B1iii—K1—K1iv | 63.21 (3) | C16—C15—H15 | 120.2 |
B1—K1—K1iv | 119.70 (3) | C14—C15—H15 | 120.2 |
C11—K1—K1iv | 78.72 (3) | C15—C16—C11 | 120.40 (15) |
C6ii—K1—K1iv | 135.87 (3) | C15—C16—K1 | 130.95 (10) |
C16—K1—K1iv | 55.86 (3) | C11—C16—K1 | 72.54 (8) |
F2—B1—F1 | 104.23 (11) | C15—C16—H16 | 119.8 |
F2—B1—O1 | 105.54 (11) | C11—C16—H16 | 119.8 |
F1—B1—O1 | 107.63 (12) | K1—C16—H16 | 69.1 |
F2—B1—O1—C11 | 151.69 (11) | B1—C1—C2—C3 | 179.90 (13) |
F1—B1—O1—C11 | −97.45 (14) | C6—C1—C2—C12 | −178.70 (13) |
C1—B1—O1—C11 | 26.22 (18) | B1—C1—C2—C12 | 2.01 (19) |
K1iii—B1—O1—C11 | 150.72 (13) | C1—C2—C3—C4 | 1.8 (2) |
K1—B1—O1—C11 | −101.56 (11) | C12—C2—C3—C4 | 179.63 (14) |
F2—B1—O1—K1iii | 0.97 (11) | C2—C3—C4—C5 | −1.1 (2) |
F1—B1—O1—K1iii | 111.83 (10) | C3—C4—C5—C6 | −0.7 (2) |
C1—B1—O1—K1iii | −124.50 (10) | C2—C1—C6—C5 | −0.9 (2) |
K1—B1—O1—K1iii | 107.72 (5) | B1—C1—C6—C5 | 178.34 (14) |
F2—B1—O1—K1 | −106.75 (9) | C2—C1—C6—K1v | −128.97 (12) |
F1—B1—O1—K1 | 4.11 (11) | B1—C1—C6—K1v | 50.29 (13) |
C1—B1—O1—K1 | 127.79 (11) | C4—C5—C6—C1 | 1.7 (2) |
K1iii—B1—O1—K1 | −107.72 (5) | C4—C5—C6—K1v | 113.06 (15) |
F2—B1—F1—K1v | −76.01 (12) | B1—O1—C11—C16 | 165.10 (13) |
O1—B1—F1—K1v | 172.24 (7) | K1iii—O1—C11—C16 | −52.50 (16) |
C1—B1—F1—K1v | 46.99 (14) | K1—O1—C11—C16 | 64.76 (12) |
K1iii—B1—F1—K1v | −131.24 (6) | B1—O1—C11—C12 | −16.10 (19) |
K1—B1—F1—K1v | 177.00 (10) | K1iii—O1—C11—C12 | 126.30 (11) |
F2—B1—F1—K1 | 106.99 (9) | K1—O1—C11—C12 | −116.44 (12) |
O1—B1—F1—K1 | −4.76 (12) | B1—O1—C11—K1 | 100.34 (12) |
C1—B1—F1—K1 | −130.01 (10) | K1iii—O1—C11—K1 | −117.26 (9) |
K1iii—B1—F1—K1 | 51.76 (9) | O1—C11—C12—C13 | 177.69 (13) |
F1—B1—F2—K1vi | 56.3 (3) | C16—C11—C12—C13 | −3.6 (2) |
O1—B1—F2—K1vi | 169.55 (14) | K1—C11—C12—C13 | 104.41 (13) |
C1—B1—F2—K1vi | −65.0 (3) | O1—C11—C12—C2 | −3.2 (2) |
K1iii—B1—F2—K1vi | 170.5 (2) | C16—C11—C12—C2 | 175.51 (13) |
K1—B1—F2—K1vi | 106.56 (19) | K1—C11—C12—C2 | −76.51 (16) |
F1—B1—F2—K1iii | −114.22 (9) | C1—C2—C12—C13 | −171.25 (13) |
O1—B1—F2—K1iii | −0.96 (11) | C3—C2—C12—C13 | 10.9 (2) |
C1—B1—F2—K1iii | 124.51 (10) | C1—C2—C12—C11 | 9.7 (2) |
K1—B1—F2—K1iii | −63.96 (7) | C3—C2—C12—C11 | −168.10 (13) |
F2—B1—C1—C6 | 40.77 (19) | C11—C12—C13—C14 | 2.3 (2) |
F1—B1—C1—C6 | −76.55 (17) | C2—C12—C13—C14 | −176.70 (14) |
O1—B1—C1—C6 | 161.72 (13) | C12—C13—C14—C15 | 0.3 (2) |
K1iii—B1—C1—C6 | 101.37 (15) | C13—C14—C15—C16 | −1.9 (2) |
K1—B1—C1—C6 | −128.40 (13) | C14—C15—C16—C11 | 0.6 (2) |
F2—B1—C1—C2 | −139.97 (13) | C14—C15—C16—K1 | −92.15 (17) |
F1—B1—C1—C2 | 102.71 (15) | O1—C11—C16—C15 | −179.02 (13) |
O1—B1—C1—C2 | −19.02 (18) | C12—C11—C16—C15 | 2.2 (2) |
K1iii—B1—C1—C2 | −79.37 (16) | K1—C11—C16—C15 | −127.73 (13) |
K1—B1—C1—C2 | 50.86 (18) | O1—C11—C16—K1 | −51.29 (10) |
C6—C1—C2—C3 | −0.8 (2) | C12—C11—C16—K1 | 129.90 (13) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x, y−1, z. |
2C24H20P+·2C12H8BF2O−·3C2H3N | Z = 2 |
Mr = 1235.89 | F(000) = 1292 |
Triclinic, P1 | Dx = 1.272 Mg m−3 |
a = 10.3527 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.5958 (5) Å | Cell parameters from 61056 reflections |
c = 23.4352 (9) Å | θ = 2.0–25.9° |
α = 86.218 (3)° | µ = 0.13 mm−1 |
β = 78.916 (3)° | T = 173 K |
γ = 87.104 (3)° | Block, colourless |
V = 3227.6 (2) Å3 | 0.42 × 0.38 × 0.29 mm |
STOE IPDS II two-circle diffractometer | 10863 reflections with I > 2σ(I) |
ω scans | Rint = 0.040 |
Absorption correction: multi-scan (X-Area; Stoe & Cie, 2001) | θmax = 25.4°, θmin = 2.0° |
Tmin = 0.947, Tmax = 0.963 | h = −12→12 |
47827 measured reflections | k = −16→16 |
11854 independent reflections | l = −27→28 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0516P)2 + 1.4271P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
11854 reflections | Δρmax = 0.48 e Å−3 |
842 parameters | Δρmin = −0.44 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.12452 (13) | 0.43049 (8) | 0.25804 (5) | 0.0398 (3) | |
B1 | 0.12323 (19) | 0.37459 (13) | 0.20674 (8) | 0.0328 (4) | |
F1 | 0.22126 (13) | 0.41208 (8) | 0.16118 (5) | 0.0551 (3) | |
F2 | 0.00205 (12) | 0.39835 (8) | 0.18908 (5) | 0.0531 (3) | |
C1 | 0.14294 (14) | 0.25805 (11) | 0.21957 (7) | 0.0292 (3) | |
C2 | 0.17145 (14) | 0.21953 (11) | 0.27317 (7) | 0.0272 (3) | |
C3 | 0.18519 (15) | 0.11698 (11) | 0.28362 (7) | 0.0315 (3) | |
H3 | 0.204651 | 0.091107 | 0.319803 | 0.038* | |
C4 | 0.17073 (16) | 0.05318 (12) | 0.24187 (8) | 0.0354 (4) | |
H4 | 0.179876 | −0.016049 | 0.249542 | 0.043* | |
C5 | 0.14293 (16) | 0.09020 (12) | 0.18890 (8) | 0.0371 (4) | |
H5 | 0.133030 | 0.046587 | 0.160114 | 0.045* | |
C6 | 0.12967 (16) | 0.19123 (12) | 0.17818 (7) | 0.0353 (4) | |
H6 | 0.111004 | 0.216017 | 0.141658 | 0.042* | |
C11 | 0.15851 (15) | 0.39085 (11) | 0.30763 (7) | 0.0312 (3) | |
C12 | 0.18343 (14) | 0.28890 (11) | 0.31781 (7) | 0.0268 (3) | |
C13 | 0.21755 (15) | 0.25770 (12) | 0.37135 (7) | 0.0311 (3) | |
H13 | 0.235772 | 0.189468 | 0.379119 | 0.037* | |
C14 | 0.22553 (16) | 0.32294 (13) | 0.41318 (7) | 0.0345 (3) | |
H14 | 0.247785 | 0.299361 | 0.449264 | 0.041* | |
C15 | 0.20102 (17) | 0.42267 (13) | 0.40237 (7) | 0.0373 (4) | |
H15 | 0.206986 | 0.467925 | 0.430872 | 0.045* | |
C16 | 0.16792 (18) | 0.45616 (12) | 0.35008 (8) | 0.0381 (4) | |
H16 | 0.151223 | 0.524744 | 0.342801 | 0.046* | |
P1 | 0.67556 (4) | 0.15494 (3) | 0.35037 (2) | 0.02367 (9) | |
C21 | 0.67013 (15) | 0.12421 (10) | 0.27748 (6) | 0.0272 (3) | |
C22 | 0.78659 (17) | 0.10811 (12) | 0.23759 (7) | 0.0356 (4) | |
H22 | 0.869235 | 0.106773 | 0.249633 | 0.043* | |
C23 | 0.7804 (2) | 0.09407 (14) | 0.18009 (8) | 0.0459 (4) | |
H23 | 0.859167 | 0.082089 | 0.152714 | 0.055* | |
C24 | 0.6604 (2) | 0.09741 (15) | 0.16243 (8) | 0.0481 (5) | |
H24 | 0.657115 | 0.086850 | 0.123079 | 0.058* | |
C25 | 0.54518 (19) | 0.11599 (13) | 0.20154 (8) | 0.0411 (4) | |
H25 | 0.463168 | 0.119617 | 0.188864 | 0.049* | |
C26 | 0.54918 (16) | 0.12932 (11) | 0.25924 (7) | 0.0322 (3) | |
H26 | 0.470016 | 0.141883 | 0.286267 | 0.039* | |
C31 | 0.53405 (14) | 0.10965 (10) | 0.39992 (6) | 0.0248 (3) | |
C32 | 0.47498 (15) | 0.02422 (11) | 0.38891 (7) | 0.0281 (3) | |
H32 | 0.505119 | −0.007380 | 0.353556 | 0.034* | |
C33 | 0.37240 (15) | −0.01386 (11) | 0.42989 (7) | 0.0318 (3) | |
H33 | 0.331854 | −0.071696 | 0.422591 | 0.038* | |
C34 | 0.32868 (15) | 0.03207 (11) | 0.48147 (7) | 0.0322 (3) | |
H34 | 0.256819 | 0.006415 | 0.508956 | 0.039* | |
C35 | 0.38893 (15) | 0.11528 (11) | 0.49337 (7) | 0.0309 (3) | |
H35 | 0.359439 | 0.145623 | 0.529190 | 0.037* | |
C36 | 0.49214 (15) | 0.15399 (11) | 0.45292 (7) | 0.0284 (3) | |
H36 | 0.534334 | 0.210452 | 0.461115 | 0.034* | |
C41 | 0.81841 (14) | 0.09717 (11) | 0.37314 (6) | 0.0266 (3) | |
C42 | 0.85557 (16) | 0.00071 (11) | 0.35834 (7) | 0.0335 (3) | |
H42 | 0.811375 | −0.031069 | 0.333132 | 0.040* | |
C43 | 0.95702 (17) | −0.04846 (13) | 0.38051 (8) | 0.0400 (4) | |
H43 | 0.983616 | −0.113748 | 0.369988 | 0.048* | |
C44 | 1.01967 (16) | −0.00275 (13) | 0.41791 (8) | 0.0402 (4) | |
H44 | 1.089368 | −0.036748 | 0.433015 | 0.048* | |
C45 | 0.98160 (16) | 0.09215 (13) | 0.43351 (8) | 0.0379 (4) | |
H45 | 1.024512 | 0.122775 | 0.459638 | 0.046* | |
C46 | 0.88125 (15) | 0.14277 (12) | 0.41124 (7) | 0.0314 (3) | |
H46 | 0.855390 | 0.208128 | 0.421831 | 0.038* | |
C51 | 0.68050 (15) | 0.28636 (10) | 0.34950 (6) | 0.0258 (3) | |
C52 | 0.79962 (15) | 0.33163 (11) | 0.32810 (7) | 0.0309 (3) | |
H52 | 0.878918 | 0.292910 | 0.318517 | 0.037* | |
C53 | 0.80107 (17) | 0.43362 (12) | 0.32097 (7) | 0.0351 (4) | |
H53 | 0.881769 | 0.465079 | 0.306699 | 0.042* | |
C54 | 0.68499 (17) | 0.48980 (11) | 0.33462 (7) | 0.0346 (4) | |
H54 | 0.686732 | 0.559677 | 0.329805 | 0.041* | |
C55 | 0.56697 (17) | 0.44518 (12) | 0.35513 (7) | 0.0345 (3) | |
H55 | 0.487928 | 0.484344 | 0.364219 | 0.041* | |
C56 | 0.56353 (15) | 0.34322 (11) | 0.36250 (7) | 0.0301 (3) | |
H56 | 0.482246 | 0.312297 | 0.376277 | 0.036* | |
O1A | 0.46591 (11) | 0.79394 (8) | 0.34012 (5) | 0.0348 (2) | |
B1A | 0.32951 (18) | 0.76328 (13) | 0.34453 (8) | 0.0312 (4) | |
F1A | 0.25501 (10) | 0.84978 (7) | 0.33229 (5) | 0.0436 (2) | |
F2A | 0.32692 (11) | 0.69946 (7) | 0.29946 (4) | 0.0425 (2) | |
C1A | 0.27336 (15) | 0.71222 (11) | 0.40733 (7) | 0.0299 (3) | |
C2A | 0.36027 (16) | 0.67457 (11) | 0.44359 (7) | 0.0289 (3) | |
C3A | 0.30921 (18) | 0.62809 (12) | 0.49817 (7) | 0.0364 (4) | |
H3A | 0.367670 | 0.602655 | 0.522687 | 0.044* | |
C4A | 0.1751 (2) | 0.61904 (13) | 0.51648 (8) | 0.0432 (4) | |
H4A | 0.141895 | 0.587255 | 0.553332 | 0.052* | |
C5A | 0.08914 (19) | 0.65624 (14) | 0.48120 (9) | 0.0457 (4) | |
H5A | −0.003151 | 0.650298 | 0.493725 | 0.055* | |
C6A | 0.13839 (17) | 0.70203 (13) | 0.42769 (8) | 0.0390 (4) | |
H6A | 0.078495 | 0.727520 | 0.403857 | 0.047* | |
C11A | 0.54740 (16) | 0.74683 (11) | 0.37201 (7) | 0.0307 (3) | |
C12A | 0.50301 (16) | 0.68660 (11) | 0.42267 (7) | 0.0296 (3) | |
C13A | 0.59866 (18) | 0.64043 (12) | 0.45160 (8) | 0.0376 (4) | |
H13A | 0.570852 | 0.598894 | 0.485508 | 0.045* | |
C14A | 0.73140 (18) | 0.65331 (14) | 0.43247 (9) | 0.0452 (4) | |
H14A | 0.793671 | 0.620652 | 0.452860 | 0.054* | |
C15A | 0.77353 (18) | 0.71413 (14) | 0.38338 (9) | 0.0463 (5) | |
H15A | 0.864899 | 0.723935 | 0.370258 | 0.056* | |
C16A | 0.68276 (17) | 0.76060 (13) | 0.35343 (8) | 0.0388 (4) | |
H16A | 0.712373 | 0.802395 | 0.319832 | 0.047* | |
P1A | 0.74154 (4) | 0.67262 (3) | 0.14593 (2) | 0.02748 (10) | |
C21A | 0.61990 (15) | 0.77059 (11) | 0.14360 (7) | 0.0290 (3) | |
C22A | 0.58843 (18) | 0.80677 (13) | 0.09096 (8) | 0.0389 (4) | |
H22A | 0.633680 | 0.781568 | 0.055405 | 0.047* | |
C23A | 0.4905 (2) | 0.87989 (15) | 0.09080 (9) | 0.0495 (5) | |
H23A | 0.469425 | 0.905880 | 0.054929 | 0.059* | |
C24A | 0.42331 (19) | 0.91521 (14) | 0.14263 (9) | 0.0466 (4) | |
H24A | 0.355582 | 0.964914 | 0.142184 | 0.056* | |
C25A | 0.45370 (18) | 0.87892 (12) | 0.19509 (8) | 0.0394 (4) | |
H25A | 0.406434 | 0.903138 | 0.230570 | 0.047* | |
C26A | 0.55279 (16) | 0.80746 (11) | 0.19586 (7) | 0.0334 (3) | |
H26A | 0.575369 | 0.783373 | 0.231790 | 0.040* | |
C31A | 0.66018 (16) | 0.56238 (11) | 0.17613 (7) | 0.0322 (3) | |
C32A | 0.72734 (19) | 0.47093 (12) | 0.16976 (9) | 0.0419 (4) | |
H32A | 0.816655 | 0.466797 | 0.150269 | 0.050* | |
C33A | 0.6618 (2) | 0.38587 (13) | 0.19234 (10) | 0.0514 (5) | |
H33A | 0.707222 | 0.323427 | 0.188851 | 0.062* | |
C34A | 0.5318 (2) | 0.39153 (14) | 0.21965 (9) | 0.0518 (5) | |
H34A | 0.487228 | 0.332857 | 0.233800 | 0.062* | |
C35A | 0.4661 (2) | 0.48134 (14) | 0.22657 (9) | 0.0487 (5) | |
H35A | 0.376676 | 0.484745 | 0.245929 | 0.058* | |
C36A | 0.52989 (18) | 0.56706 (13) | 0.20543 (8) | 0.0388 (4) | |
H36A | 0.484588 | 0.629246 | 0.210937 | 0.047* | |
C41A | 0.85613 (15) | 0.70925 (11) | 0.18844 (7) | 0.0294 (3) | |
C42A | 0.93100 (18) | 0.63853 (12) | 0.21477 (8) | 0.0374 (4) | |
H42A | 0.917951 | 0.570346 | 0.212493 | 0.045* | |
C43A | 1.0246 (2) | 0.66824 (13) | 0.24431 (9) | 0.0457 (4) | |
H43A | 1.075962 | 0.620113 | 0.262275 | 0.055* | |
C44A | 1.04410 (19) | 0.76758 (13) | 0.24791 (9) | 0.0437 (4) | |
H44A | 1.108785 | 0.787400 | 0.268126 | 0.052* | |
C45A | 0.96920 (18) | 0.83766 (13) | 0.22203 (8) | 0.0417 (4) | |
H45A | 0.981968 | 0.905736 | 0.224882 | 0.050* | |
C46A | 0.87565 (17) | 0.80948 (12) | 0.19197 (8) | 0.0353 (4) | |
H46A | 0.825052 | 0.857948 | 0.173851 | 0.042* | |
C51A | 0.82688 (17) | 0.65247 (13) | 0.07317 (7) | 0.0368 (4) | |
C52A | 0.7733 (2) | 0.59274 (16) | 0.03807 (9) | 0.0542 (5) | |
H52A | 0.695692 | 0.558136 | 0.053530 | 0.065* | |
C53A | 0.8346 (3) | 0.5845 (2) | −0.01946 (10) | 0.0737 (8) | |
H53A | 0.798253 | 0.544150 | −0.043517 | 0.088* | |
C54A | 0.9469 (3) | 0.6338 (2) | −0.04215 (10) | 0.0799 (9) | |
H54A | 0.987884 | 0.627627 | −0.081730 | 0.096* | |
C55A | 1.0004 (3) | 0.6921 (2) | −0.00771 (11) | 0.0783 (8) | |
H55A | 1.078704 | 0.725655 | −0.023523 | 0.094* | |
C56A | 0.9404 (2) | 0.70232 (17) | 0.05041 (9) | 0.0543 (5) | |
H56A | 0.977155 | 0.743069 | 0.074091 | 0.065* | |
N61 | 1.0162 (5) | 0.9547 (3) | 0.07570 (13) | 0.1405 (15) | |
C62 | 1.1110 (4) | 0.9774 (3) | 0.04320 (13) | 0.0991 (11) | |
C63 | 1.2218 (4) | 1.0112 (5) | 0.0041 (2) | 0.156 (2) | |
H63A | 1.195474 | 1.037192 | −0.032195 | 0.235* | |
H63B | 1.286666 | 0.956532 | −0.004253 | 0.235* | |
H63C | 1.260647 | 1.063580 | 0.021245 | 0.235* | |
N71 | 0.4432 (5) | 0.1390 (3) | 0.05427 (14) | 0.1466 (16) | |
C72 | 0.4540 (4) | 0.2169 (3) | 0.06671 (11) | 0.0886 (9) | |
C73 | 0.4630 (3) | 0.3133 (3) | 0.08298 (14) | 0.0933 (10) | |
H73A | 0.390831 | 0.327689 | 0.115388 | 0.140* | |
H73B | 0.457012 | 0.359912 | 0.049792 | 0.140* | |
H73C | 0.547505 | 0.319626 | 0.095136 | 0.140* | |
N81 | 0.4309 (7) | 0.5722 (6) | 0.0455 (4) | 0.143 (3) | 0.545 (5) |
C82 | 0.3563 (6) | 0.6043 (5) | 0.0833 (4) | 0.098 (2) | 0.545 (5) |
N81' | 0.2713 (7) | 0.7449 (6) | 0.0256 (4) | 0.118 (3) | 0.455 (5) |
C82' | 0.2828 (6) | 0.6973 (5) | 0.0668 (4) | 0.0790 (19) | 0.455 (5) |
C83 | 0.2753 (5) | 0.6434 (3) | 0.1246 (2) | 0.1204 (14) | |
H83A | 0.255574 | 0.595002 | 0.157706 | 0.181* | 0.545 (5) |
H83B | 0.193732 | 0.664258 | 0.111112 | 0.181* | 0.545 (5) |
H83C | 0.314423 | 0.700794 | 0.136783 | 0.181* | 0.545 (5) |
H83D | 0.234341 | 0.580029 | 0.124309 | 0.181* | 0.455 (5) |
H83E | 0.222277 | 0.682864 | 0.154807 | 0.181* | 0.455 (5) |
H83F | 0.364246 | 0.631736 | 0.132872 | 0.181* | 0.455 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0612 (8) | 0.0272 (6) | 0.0336 (6) | 0.0045 (5) | −0.0171 (6) | −0.0024 (5) |
B1 | 0.0377 (9) | 0.0315 (9) | 0.0300 (9) | 0.0016 (7) | −0.0090 (7) | −0.0014 (7) |
F1 | 0.0722 (8) | 0.0427 (6) | 0.0432 (6) | −0.0100 (5) | 0.0072 (5) | 0.0038 (5) |
F2 | 0.0583 (7) | 0.0446 (6) | 0.0648 (7) | 0.0157 (5) | −0.0346 (6) | −0.0109 (5) |
C1 | 0.0244 (7) | 0.0316 (8) | 0.0313 (8) | −0.0013 (6) | −0.0040 (6) | −0.0041 (6) |
C2 | 0.0209 (7) | 0.0284 (7) | 0.0313 (8) | −0.0018 (5) | −0.0022 (6) | −0.0027 (6) |
C3 | 0.0286 (8) | 0.0294 (8) | 0.0360 (8) | −0.0016 (6) | −0.0050 (6) | −0.0010 (6) |
C4 | 0.0305 (8) | 0.0279 (8) | 0.0471 (10) | −0.0010 (6) | −0.0040 (7) | −0.0063 (7) |
C5 | 0.0346 (8) | 0.0357 (9) | 0.0427 (10) | −0.0004 (7) | −0.0076 (7) | −0.0146 (7) |
C6 | 0.0351 (8) | 0.0387 (9) | 0.0334 (9) | 0.0001 (7) | −0.0086 (7) | −0.0068 (7) |
C11 | 0.0319 (8) | 0.0307 (8) | 0.0314 (8) | −0.0008 (6) | −0.0067 (6) | −0.0019 (6) |
C12 | 0.0208 (7) | 0.0293 (7) | 0.0295 (8) | −0.0024 (5) | −0.0024 (6) | −0.0018 (6) |
C13 | 0.0279 (7) | 0.0325 (8) | 0.0326 (8) | −0.0001 (6) | −0.0055 (6) | −0.0003 (6) |
C14 | 0.0310 (8) | 0.0446 (9) | 0.0284 (8) | 0.0007 (7) | −0.0066 (6) | −0.0032 (7) |
C15 | 0.0377 (9) | 0.0415 (9) | 0.0337 (9) | −0.0009 (7) | −0.0064 (7) | −0.0119 (7) |
C16 | 0.0471 (10) | 0.0299 (8) | 0.0382 (9) | 0.0008 (7) | −0.0089 (7) | −0.0065 (7) |
P1 | 0.02439 (18) | 0.02135 (18) | 0.02522 (19) | −0.00115 (13) | −0.00411 (14) | −0.00261 (13) |
C21 | 0.0320 (8) | 0.0223 (7) | 0.0270 (7) | −0.0013 (6) | −0.0051 (6) | −0.0019 (5) |
C22 | 0.0360 (8) | 0.0366 (8) | 0.0334 (9) | 0.0030 (7) | −0.0045 (7) | −0.0056 (7) |
C23 | 0.0520 (11) | 0.0497 (11) | 0.0327 (9) | 0.0048 (8) | 0.0010 (8) | −0.0102 (8) |
C24 | 0.0655 (13) | 0.0507 (11) | 0.0305 (9) | −0.0041 (9) | −0.0116 (9) | −0.0105 (8) |
C25 | 0.0480 (10) | 0.0427 (9) | 0.0367 (9) | −0.0070 (8) | −0.0167 (8) | −0.0031 (7) |
C26 | 0.0351 (8) | 0.0298 (8) | 0.0328 (8) | −0.0029 (6) | −0.0085 (7) | −0.0015 (6) |
C31 | 0.0250 (7) | 0.0228 (7) | 0.0267 (7) | −0.0004 (5) | −0.0055 (6) | −0.0006 (5) |
C32 | 0.0302 (7) | 0.0243 (7) | 0.0300 (8) | −0.0009 (6) | −0.0059 (6) | −0.0032 (6) |
C33 | 0.0304 (8) | 0.0265 (7) | 0.0387 (9) | −0.0050 (6) | −0.0069 (7) | −0.0001 (6) |
C34 | 0.0282 (7) | 0.0319 (8) | 0.0343 (8) | −0.0026 (6) | −0.0024 (6) | 0.0038 (6) |
C35 | 0.0327 (8) | 0.0317 (8) | 0.0269 (8) | 0.0025 (6) | −0.0030 (6) | −0.0024 (6) |
C36 | 0.0309 (8) | 0.0251 (7) | 0.0298 (8) | −0.0017 (6) | −0.0068 (6) | −0.0036 (6) |
C41 | 0.0248 (7) | 0.0259 (7) | 0.0283 (7) | −0.0020 (6) | −0.0034 (6) | 0.0006 (6) |
C42 | 0.0341 (8) | 0.0285 (8) | 0.0381 (9) | 0.0007 (6) | −0.0079 (7) | −0.0029 (6) |
C43 | 0.0373 (9) | 0.0323 (8) | 0.0477 (10) | 0.0078 (7) | −0.0054 (8) | 0.0021 (7) |
C44 | 0.0293 (8) | 0.0461 (10) | 0.0432 (10) | 0.0018 (7) | −0.0080 (7) | 0.0120 (8) |
C45 | 0.0317 (8) | 0.0474 (10) | 0.0363 (9) | −0.0106 (7) | −0.0106 (7) | 0.0058 (7) |
C46 | 0.0322 (8) | 0.0300 (8) | 0.0322 (8) | −0.0062 (6) | −0.0055 (6) | −0.0001 (6) |
C51 | 0.0300 (7) | 0.0227 (7) | 0.0250 (7) | −0.0019 (6) | −0.0059 (6) | −0.0019 (5) |
C52 | 0.0297 (8) | 0.0291 (8) | 0.0331 (8) | −0.0018 (6) | −0.0042 (6) | −0.0003 (6) |
C53 | 0.0395 (9) | 0.0300 (8) | 0.0365 (9) | −0.0104 (7) | −0.0078 (7) | 0.0020 (6) |
C54 | 0.0490 (10) | 0.0229 (7) | 0.0341 (8) | −0.0040 (7) | −0.0127 (7) | −0.0028 (6) |
C55 | 0.0398 (9) | 0.0273 (8) | 0.0373 (9) | 0.0045 (6) | −0.0097 (7) | −0.0065 (6) |
C56 | 0.0299 (8) | 0.0282 (7) | 0.0324 (8) | −0.0013 (6) | −0.0059 (6) | −0.0039 (6) |
O1A | 0.0374 (6) | 0.0347 (6) | 0.0329 (6) | −0.0041 (5) | −0.0090 (5) | 0.0023 (5) |
B1A | 0.0355 (9) | 0.0288 (8) | 0.0313 (9) | 0.0030 (7) | −0.0116 (7) | −0.0043 (7) |
F1A | 0.0479 (6) | 0.0391 (5) | 0.0445 (6) | 0.0096 (4) | −0.0151 (5) | 0.0034 (4) |
F2A | 0.0525 (6) | 0.0447 (6) | 0.0326 (5) | −0.0058 (5) | −0.0103 (4) | −0.0106 (4) |
C1A | 0.0334 (8) | 0.0255 (7) | 0.0320 (8) | 0.0011 (6) | −0.0080 (6) | −0.0071 (6) |
C2A | 0.0371 (8) | 0.0233 (7) | 0.0279 (8) | −0.0003 (6) | −0.0081 (6) | −0.0072 (6) |
C3A | 0.0514 (10) | 0.0313 (8) | 0.0287 (8) | −0.0047 (7) | −0.0117 (7) | −0.0048 (6) |
C4A | 0.0583 (11) | 0.0386 (9) | 0.0302 (9) | −0.0129 (8) | 0.0026 (8) | −0.0069 (7) |
C5A | 0.0385 (9) | 0.0481 (10) | 0.0477 (11) | −0.0071 (8) | 0.0033 (8) | −0.0126 (8) |
C6A | 0.0348 (9) | 0.0384 (9) | 0.0444 (10) | 0.0019 (7) | −0.0082 (7) | −0.0065 (7) |
C11A | 0.0344 (8) | 0.0278 (7) | 0.0318 (8) | −0.0007 (6) | −0.0086 (6) | −0.0104 (6) |
C12A | 0.0359 (8) | 0.0255 (7) | 0.0304 (8) | 0.0013 (6) | −0.0118 (6) | −0.0096 (6) |
C13A | 0.0447 (9) | 0.0348 (8) | 0.0383 (9) | 0.0050 (7) | −0.0189 (8) | −0.0111 (7) |
C14A | 0.0422 (10) | 0.0469 (10) | 0.0543 (11) | 0.0090 (8) | −0.0247 (9) | −0.0216 (9) |
C15A | 0.0319 (9) | 0.0531 (11) | 0.0588 (12) | −0.0012 (8) | −0.0126 (8) | −0.0290 (9) |
C16A | 0.0377 (9) | 0.0399 (9) | 0.0398 (9) | −0.0087 (7) | −0.0042 (7) | −0.0136 (7) |
P1A | 0.0303 (2) | 0.02541 (19) | 0.0278 (2) | 0.00102 (15) | −0.00815 (15) | −0.00298 (15) |
C21A | 0.0310 (8) | 0.0254 (7) | 0.0314 (8) | −0.0003 (6) | −0.0079 (6) | −0.0017 (6) |
C22A | 0.0455 (10) | 0.0404 (9) | 0.0307 (9) | 0.0091 (7) | −0.0093 (7) | −0.0040 (7) |
C23A | 0.0583 (12) | 0.0509 (11) | 0.0411 (10) | 0.0184 (9) | −0.0198 (9) | −0.0010 (8) |
C24A | 0.0459 (10) | 0.0419 (10) | 0.0513 (11) | 0.0160 (8) | −0.0116 (9) | −0.0055 (8) |
C25A | 0.0419 (9) | 0.0347 (9) | 0.0400 (9) | 0.0045 (7) | −0.0032 (7) | −0.0075 (7) |
C26A | 0.0395 (9) | 0.0297 (8) | 0.0310 (8) | −0.0006 (6) | −0.0071 (7) | −0.0018 (6) |
C31A | 0.0386 (8) | 0.0265 (7) | 0.0353 (8) | −0.0017 (6) | −0.0162 (7) | −0.0022 (6) |
C32A | 0.0461 (10) | 0.0307 (8) | 0.0543 (11) | 0.0032 (7) | −0.0227 (9) | −0.0073 (7) |
C33A | 0.0759 (14) | 0.0244 (8) | 0.0626 (13) | −0.0003 (8) | −0.0355 (11) | −0.0024 (8) |
C34A | 0.0721 (14) | 0.0361 (10) | 0.0525 (12) | −0.0190 (9) | −0.0242 (10) | 0.0066 (8) |
C35A | 0.0535 (11) | 0.0443 (10) | 0.0489 (11) | −0.0154 (9) | −0.0101 (9) | 0.0052 (8) |
C36A | 0.0427 (9) | 0.0328 (8) | 0.0413 (9) | −0.0048 (7) | −0.0089 (8) | 0.0007 (7) |
C41A | 0.0321 (8) | 0.0282 (7) | 0.0287 (8) | −0.0029 (6) | −0.0072 (6) | −0.0013 (6) |
C42A | 0.0454 (9) | 0.0273 (8) | 0.0431 (10) | −0.0011 (7) | −0.0180 (8) | −0.0004 (7) |
C43A | 0.0519 (11) | 0.0367 (9) | 0.0557 (12) | 0.0000 (8) | −0.0301 (9) | 0.0020 (8) |
C44A | 0.0457 (10) | 0.0421 (10) | 0.0496 (11) | −0.0069 (8) | −0.0227 (8) | −0.0036 (8) |
C45A | 0.0459 (10) | 0.0307 (8) | 0.0524 (11) | −0.0079 (7) | −0.0170 (8) | −0.0031 (7) |
C46A | 0.0385 (9) | 0.0272 (8) | 0.0424 (9) | −0.0021 (6) | −0.0134 (7) | 0.0003 (7) |
C51A | 0.0390 (9) | 0.0409 (9) | 0.0303 (8) | 0.0125 (7) | −0.0087 (7) | −0.0054 (7) |
C52A | 0.0614 (13) | 0.0625 (13) | 0.0420 (11) | 0.0127 (10) | −0.0167 (9) | −0.0194 (9) |
C53A | 0.093 (2) | 0.0893 (18) | 0.0426 (12) | 0.0362 (16) | −0.0244 (13) | −0.0278 (12) |
C54A | 0.092 (2) | 0.107 (2) | 0.0323 (11) | 0.0490 (17) | −0.0035 (12) | −0.0099 (13) |
C55A | 0.0646 (15) | 0.108 (2) | 0.0500 (14) | 0.0099 (14) | 0.0137 (12) | 0.0074 (14) |
C56A | 0.0503 (11) | 0.0681 (13) | 0.0401 (11) | 0.0011 (10) | 0.0001 (9) | 0.0005 (9) |
N61 | 0.210 (4) | 0.146 (3) | 0.0611 (18) | −0.070 (3) | 0.001 (2) | −0.0008 (18) |
C62 | 0.147 (3) | 0.099 (2) | 0.0497 (16) | −0.032 (2) | −0.0075 (18) | −0.0033 (15) |
C63 | 0.090 (3) | 0.255 (6) | 0.107 (3) | −0.002 (3) | 0.003 (2) | 0.050 (4) |
N71 | 0.277 (5) | 0.102 (2) | 0.0662 (18) | 0.009 (3) | −0.049 (2) | −0.0087 (17) |
C72 | 0.125 (3) | 0.101 (2) | 0.0403 (13) | 0.025 (2) | −0.0230 (15) | −0.0093 (14) |
C73 | 0.096 (2) | 0.109 (2) | 0.079 (2) | 0.0287 (18) | −0.0243 (17) | −0.0335 (18) |
N81 | 0.101 (5) | 0.151 (6) | 0.160 (7) | −0.036 (4) | 0.009 (4) | 0.032 (5) |
C82 | 0.061 (3) | 0.083 (4) | 0.143 (7) | −0.022 (3) | −0.010 (4) | 0.034 (4) |
N81' | 0.081 (4) | 0.140 (6) | 0.139 (7) | −0.021 (4) | −0.039 (4) | 0.003 (5) |
C82' | 0.050 (3) | 0.087 (4) | 0.103 (5) | −0.017 (3) | −0.019 (3) | −0.001 (4) |
C83 | 0.114 (3) | 0.096 (3) | 0.154 (4) | −0.003 (2) | −0.041 (3) | 0.013 (3) |
O1—C11 | 1.3492 (19) | C3A—H3A | 0.9500 |
O1—B1 | 1.466 (2) | C4A—C5A | 1.383 (3) |
B1—F2 | 1.411 (2) | C4A—H4A | 0.9500 |
B1—F1 | 1.412 (2) | C5A—C6A | 1.380 (3) |
B1—C1 | 1.603 (2) | C5A—H5A | 0.9500 |
C1—C6 | 1.402 (2) | C6A—H6A | 0.9500 |
C1—C2 | 1.407 (2) | C11A—C16A | 1.403 (2) |
C2—C3 | 1.404 (2) | C11A—C12A | 1.411 (2) |
C2—C12 | 1.480 (2) | C12A—C13A | 1.405 (2) |
C3—C4 | 1.383 (2) | C13A—C14A | 1.377 (3) |
C3—H3 | 0.9500 | C13A—H13A | 0.9500 |
C4—C5 | 1.385 (3) | C14A—C15A | 1.384 (3) |
C4—H4 | 0.9500 | C14A—H14A | 0.9500 |
C5—C6 | 1.385 (2) | C15A—C16A | 1.382 (3) |
C5—H5 | 0.9500 | C15A—H15A | 0.9500 |
C6—H6 | 0.9500 | C16A—H16A | 0.9500 |
C11—C16 | 1.397 (2) | P1A—C21A | 1.7917 (15) |
C11—C12 | 1.410 (2) | P1A—C31A | 1.7930 (16) |
C12—C13 | 1.401 (2) | P1A—C51A | 1.7947 (17) |
C13—C14 | 1.381 (2) | P1A—C41A | 1.7966 (15) |
C13—H13 | 0.9500 | C21A—C22A | 1.389 (2) |
C14—C15 | 1.383 (2) | C21A—C26A | 1.397 (2) |
C14—H14 | 0.9500 | C22A—C23A | 1.384 (2) |
C15—C16 | 1.378 (2) | C22A—H22A | 0.9500 |
C15—H15 | 0.9500 | C23A—C24A | 1.381 (3) |
C16—H16 | 0.9500 | C23A—H23A | 0.9500 |
P1—C51 | 1.7887 (14) | C24A—C25A | 1.381 (3) |
P1—C31 | 1.7935 (15) | C24A—H24A | 0.9500 |
P1—C41 | 1.7944 (15) | C25A—C26A | 1.379 (2) |
P1—C21 | 1.7970 (15) | C25A—H25A | 0.9500 |
C21—C22 | 1.394 (2) | C26A—H26A | 0.9500 |
C21—C26 | 1.396 (2) | C31A—C36A | 1.391 (2) |
C22—C23 | 1.387 (2) | C31A—C32A | 1.396 (2) |
C22—H22 | 0.9500 | C32A—C33A | 1.392 (3) |
C23—C24 | 1.380 (3) | C32A—H32A | 0.9500 |
C23—H23 | 0.9500 | C33A—C34A | 1.376 (3) |
C24—C25 | 1.381 (3) | C33A—H33A | 0.9500 |
C24—H24 | 0.9500 | C34A—C35A | 1.371 (3) |
C25—C26 | 1.385 (2) | C34A—H34A | 0.9500 |
C25—H25 | 0.9500 | C35A—C36A | 1.384 (2) |
C26—H26 | 0.9500 | C35A—H35A | 0.9500 |
C31—C36 | 1.400 (2) | C36A—H36A | 0.9500 |
C31—C32 | 1.400 (2) | C41A—C42A | 1.391 (2) |
C32—C33 | 1.384 (2) | C41A—C46A | 1.398 (2) |
C32—H32 | 0.9500 | C42A—C43A | 1.384 (2) |
C33—C34 | 1.384 (2) | C42A—H42A | 0.9500 |
C33—H33 | 0.9500 | C43A—C44A | 1.386 (3) |
C34—C35 | 1.388 (2) | C43A—H43A | 0.9500 |
C34—H34 | 0.9500 | C44A—C45A | 1.381 (3) |
C35—C36 | 1.385 (2) | C44A—H44A | 0.9500 |
C35—H35 | 0.9500 | C45A—C46A | 1.385 (2) |
C36—H36 | 0.9500 | C45A—H45A | 0.9500 |
C41—C46 | 1.393 (2) | C46A—H46A | 0.9500 |
C41—C42 | 1.395 (2) | C51A—C56A | 1.385 (3) |
C42—C43 | 1.383 (2) | C51A—C52A | 1.397 (3) |
C42—H42 | 0.9500 | C52A—C53A | 1.384 (3) |
C43—C44 | 1.381 (3) | C52A—H52A | 0.9500 |
C43—H43 | 0.9500 | C53A—C54A | 1.371 (4) |
C44—C45 | 1.382 (3) | C53A—H53A | 0.9500 |
C44—H44 | 0.9500 | C54A—C55A | 1.373 (4) |
C45—C46 | 1.384 (2) | C54A—H54A | 0.9500 |
C45—H45 | 0.9500 | C55A—C56A | 1.397 (3) |
C46—H46 | 0.9500 | C55A—H55A | 0.9500 |
C51—C52 | 1.396 (2) | C56A—H56A | 0.9500 |
C51—C56 | 1.397 (2) | N61—C62 | 1.162 (5) |
C52—C53 | 1.386 (2) | C62—C63 | 1.400 (5) |
C52—H52 | 0.9500 | C63—H63A | 0.9800 |
C53—C54 | 1.386 (2) | C63—H63B | 0.9800 |
C53—H53 | 0.9500 | C63—H63C | 0.9800 |
C54—C55 | 1.379 (2) | N71—C72 | 1.133 (4) |
C54—H54 | 0.9500 | C72—C73 | 1.401 (5) |
C55—C56 | 1.387 (2) | C73—H73A | 0.9800 |
C55—H55 | 0.9500 | C73—H73B | 0.9800 |
C56—H56 | 0.9500 | C73—H73C | 0.9800 |
O1A—C11A | 1.3435 (19) | N81—C82 | 1.152 (11) |
O1A—B1A | 1.475 (2) | C82—C83 | 1.279 (9) |
B1A—F2A | 1.415 (2) | N81'—C82' | 1.150 (10) |
B1A—F1A | 1.417 (2) | C82'—C83 | 1.488 (9) |
B1A—C1A | 1.601 (2) | C83—H83A | 0.9800 |
C1A—C6A | 1.398 (2) | C83—H83B | 0.9800 |
C1A—C2A | 1.408 (2) | C83—H83C | 0.9800 |
C2A—C3A | 1.408 (2) | C83—H83D | 0.9800 |
C2A—C12A | 1.479 (2) | C83—H83E | 0.9800 |
C3A—C4A | 1.381 (3) | C83—H83F | 0.9800 |
C11—O1—B1 | 123.95 (13) | C4A—C3A—H3A | 119.6 |
F2—B1—F1 | 105.79 (14) | C2A—C3A—H3A | 119.6 |
F2—B1—O1 | 106.94 (14) | C3A—C4A—C5A | 120.05 (17) |
F1—B1—O1 | 107.56 (14) | C3A—C4A—H4A | 120.0 |
F2—B1—C1 | 111.46 (14) | C5A—C4A—H4A | 120.0 |
F1—B1—C1 | 112.30 (14) | C6A—C5A—C4A | 119.53 (17) |
O1—B1—C1 | 112.40 (13) | C6A—C5A—H5A | 120.2 |
C6—C1—C2 | 117.90 (14) | C4A—C5A—H5A | 120.2 |
C6—C1—B1 | 121.04 (14) | C5A—C6A—C1A | 122.28 (17) |
C2—C1—B1 | 121.05 (13) | C5A—C6A—H6A | 118.9 |
C3—C2—C1 | 119.71 (14) | C1A—C6A—H6A | 118.9 |
C3—C2—C12 | 121.62 (14) | O1A—C11A—C16A | 117.06 (15) |
C1—C2—C12 | 118.66 (13) | O1A—C11A—C12A | 123.26 (14) |
C4—C3—C2 | 120.81 (15) | C16A—C11A—C12A | 119.67 (15) |
C4—C3—H3 | 119.6 | C13A—C12A—C11A | 117.58 (15) |
C2—C3—H3 | 119.6 | C13A—C12A—C2A | 122.52 (15) |
C3—C4—C5 | 120.03 (15) | C11A—C12A—C2A | 119.90 (14) |
C3—C4—H4 | 120.0 | C14A—C13A—C12A | 122.25 (18) |
C5—C4—H4 | 120.0 | C14A—C13A—H13A | 118.9 |
C6—C5—C4 | 119.52 (15) | C12A—C13A—H13A | 118.9 |
C6—C5—H5 | 120.2 | C13A—C14A—C15A | 119.61 (17) |
C4—C5—H5 | 120.2 | C13A—C14A—H14A | 120.2 |
C5—C6—C1 | 122.02 (16) | C15A—C14A—H14A | 120.2 |
C5—C6—H6 | 119.0 | C16A—C15A—C14A | 120.04 (17) |
C1—C6—H6 | 119.0 | C16A—C15A—H15A | 120.0 |
O1—C11—C16 | 116.71 (14) | C14A—C15A—H15A | 120.0 |
O1—C11—C12 | 123.23 (14) | C15A—C16A—C11A | 120.84 (18) |
C16—C11—C12 | 120.06 (15) | C15A—C16A—H16A | 119.6 |
C13—C12—C11 | 117.27 (14) | C11A—C16A—H16A | 119.6 |
C13—C12—C2 | 122.68 (14) | C21A—P1A—C31A | 108.71 (7) |
C11—C12—C2 | 120.05 (14) | C21A—P1A—C51A | 109.11 (7) |
C14—C13—C12 | 122.13 (15) | C31A—P1A—C51A | 108.93 (8) |
C14—C13—H13 | 118.9 | C21A—P1A—C41A | 108.19 (7) |
C12—C13—H13 | 118.9 | C31A—P1A—C41A | 112.38 (7) |
C13—C14—C15 | 119.78 (15) | C51A—P1A—C41A | 109.48 (8) |
C13—C14—H14 | 120.1 | C22A—C21A—C26A | 120.21 (15) |
C15—C14—H14 | 120.1 | C22A—C21A—P1A | 120.74 (12) |
C16—C15—C14 | 119.73 (15) | C26A—C21A—P1A | 119.00 (12) |
C16—C15—H15 | 120.1 | C23A—C22A—C21A | 119.36 (16) |
C14—C15—H15 | 120.1 | C23A—C22A—H22A | 120.3 |
C15—C16—C11 | 121.03 (16) | C21A—C22A—H22A | 120.3 |
C15—C16—H16 | 119.5 | C24A—C23A—C22A | 120.20 (17) |
C11—C16—H16 | 119.5 | C24A—C23A—H23A | 119.9 |
C51—P1—C31 | 111.54 (7) | C22A—C23A—H23A | 119.9 |
C51—P1—C41 | 110.88 (7) | C25A—C24A—C23A | 120.61 (16) |
C31—P1—C41 | 107.22 (7) | C25A—C24A—H24A | 119.7 |
C51—P1—C21 | 106.97 (7) | C23A—C24A—H24A | 119.7 |
C31—P1—C21 | 110.05 (7) | C26A—C25A—C24A | 119.84 (16) |
C41—P1—C21 | 110.20 (7) | C26A—C25A—H25A | 120.1 |
C22—C21—C26 | 120.23 (14) | C24A—C25A—H25A | 120.1 |
C22—C21—P1 | 120.21 (12) | C25A—C26A—C21A | 119.77 (15) |
C26—C21—P1 | 119.04 (12) | C25A—C26A—H26A | 120.1 |
C23—C22—C21 | 119.20 (16) | C21A—C26A—H26A | 120.1 |
C23—C22—H22 | 120.4 | C36A—C31A—C32A | 119.58 (16) |
C21—C22—H22 | 120.4 | C36A—C31A—P1A | 120.51 (12) |
C24—C23—C22 | 120.38 (17) | C32A—C31A—P1A | 119.90 (14) |
C24—C23—H23 | 119.8 | C33A—C32A—C31A | 119.17 (19) |
C22—C23—H23 | 119.8 | C33A—C32A—H32A | 120.4 |
C23—C24—C25 | 120.50 (17) | C31A—C32A—H32A | 120.4 |
C23—C24—H24 | 119.8 | C34A—C33A—C32A | 120.51 (18) |
C25—C24—H24 | 119.8 | C34A—C33A—H33A | 119.7 |
C24—C25—C26 | 120.00 (17) | C32A—C33A—H33A | 119.7 |
C24—C25—H25 | 120.0 | C35A—C34A—C33A | 120.38 (18) |
C26—C25—H25 | 120.0 | C35A—C34A—H34A | 119.8 |
C25—C26—C21 | 119.65 (16) | C33A—C34A—H34A | 119.8 |
C25—C26—H26 | 120.2 | C34A—C35A—C36A | 120.1 (2) |
C21—C26—H26 | 120.2 | C34A—C35A—H35A | 119.9 |
C36—C31—C32 | 119.94 (14) | C36A—C35A—H35A | 119.9 |
C36—C31—P1 | 119.19 (11) | C35A—C36A—C31A | 120.16 (17) |
C32—C31—P1 | 120.49 (11) | C35A—C36A—H36A | 119.9 |
C33—C32—C31 | 119.56 (14) | C31A—C36A—H36A | 119.9 |
C33—C32—H32 | 120.2 | C42A—C41A—C46A | 120.00 (14) |
C31—C32—H32 | 120.2 | C42A—C41A—P1A | 120.37 (12) |
C32—C33—C34 | 120.22 (14) | C46A—C41A—P1A | 119.52 (12) |
C32—C33—H33 | 119.9 | C43A—C42A—C41A | 119.54 (15) |
C34—C33—H33 | 119.9 | C43A—C42A—H42A | 120.2 |
C33—C34—C35 | 120.58 (15) | C41A—C42A—H42A | 120.2 |
C33—C34—H34 | 119.7 | C42A—C43A—C44A | 120.58 (16) |
C35—C34—H34 | 119.7 | C42A—C43A—H43A | 119.7 |
C36—C35—C34 | 119.87 (14) | C44A—C43A—H43A | 119.7 |
C36—C35—H35 | 120.1 | C45A—C44A—C43A | 119.80 (16) |
C34—C35—H35 | 120.1 | C45A—C44A—H44A | 120.1 |
C35—C36—C31 | 119.78 (14) | C43A—C44A—H44A | 120.1 |
C35—C36—H36 | 120.1 | C44A—C45A—C46A | 120.52 (16) |
C31—C36—H36 | 120.1 | C44A—C45A—H45A | 119.7 |
C46—C41—C42 | 120.02 (14) | C46A—C45A—H45A | 119.7 |
C46—C41—P1 | 120.48 (12) | C45A—C46A—C41A | 119.56 (15) |
C42—C41—P1 | 118.99 (11) | C45A—C46A—H46A | 120.2 |
C43—C42—C41 | 119.73 (15) | C41A—C46A—H46A | 120.2 |
C43—C42—H42 | 120.1 | C56A—C51A—C52A | 120.02 (18) |
C41—C42—H42 | 120.1 | C56A—C51A—P1A | 119.76 (14) |
C44—C43—C42 | 120.06 (16) | C52A—C51A—P1A | 120.03 (15) |
C44—C43—H43 | 120.0 | C53A—C52A—C51A | 119.3 (2) |
C42—C43—H43 | 120.0 | C53A—C52A—H52A | 120.3 |
C43—C44—C45 | 120.40 (15) | C51A—C52A—H52A | 120.3 |
C43—C44—H44 | 119.8 | C54A—C53A—C52A | 120.8 (2) |
C45—C44—H44 | 119.8 | C54A—C53A—H53A | 119.6 |
C44—C45—C46 | 120.28 (16) | C52A—C53A—H53A | 119.6 |
C44—C45—H45 | 119.9 | C53A—C54A—C55A | 120.1 (2) |
C46—C45—H45 | 119.9 | C53A—C54A—H54A | 120.0 |
C45—C46—C41 | 119.51 (15) | C55A—C54A—H54A | 120.0 |
C45—C46—H46 | 120.2 | C54A—C55A—C56A | 120.5 (3) |
C41—C46—H46 | 120.2 | C54A—C55A—H55A | 119.8 |
C52—C51—C56 | 120.30 (14) | C56A—C55A—H55A | 119.8 |
C52—C51—P1 | 119.14 (11) | C51A—C56A—C55A | 119.3 (2) |
C56—C51—P1 | 119.98 (11) | C51A—C56A—H56A | 120.3 |
C53—C52—C51 | 119.36 (15) | C55A—C56A—H56A | 120.3 |
C53—C52—H52 | 120.3 | N61—C62—C63 | 176.1 (5) |
C51—C52—H52 | 120.3 | C62—C63—H63A | 109.5 |
C52—C53—C54 | 120.12 (15) | C62—C63—H63B | 109.5 |
C52—C53—H53 | 119.9 | H63A—C63—H63B | 109.5 |
C54—C53—H53 | 119.9 | C62—C63—H63C | 109.5 |
C55—C54—C53 | 120.61 (14) | H63A—C63—H63C | 109.5 |
C55—C54—H54 | 119.7 | H63B—C63—H63C | 109.5 |
C53—C54—H54 | 119.7 | N71—C72—C73 | 178.1 (5) |
C54—C55—C56 | 120.10 (15) | C72—C73—H73A | 109.5 |
C54—C55—H55 | 119.9 | C72—C73—H73B | 109.5 |
C56—C55—H55 | 119.9 | H73A—C73—H73B | 109.5 |
C55—C56—C51 | 119.49 (14) | C72—C73—H73C | 109.5 |
C55—C56—H56 | 120.3 | H73A—C73—H73C | 109.5 |
C51—C56—H56 | 120.3 | H73B—C73—H73C | 109.5 |
C11A—O1A—B1A | 121.33 (13) | N81—C82—C83 | 177.7 (7) |
F2A—B1A—F1A | 106.56 (13) | N81'—C82'—C83 | 170.1 (8) |
F2A—B1A—O1A | 108.49 (14) | C82—C83—H83A | 109.5 |
F1A—B1A—O1A | 106.11 (13) | C82—C83—H83B | 109.5 |
F2A—B1A—C1A | 111.64 (13) | H83A—C83—H83B | 109.5 |
F1A—B1A—C1A | 112.18 (14) | C82—C83—H83C | 109.5 |
O1A—B1A—C1A | 111.55 (13) | H83A—C83—H83C | 109.5 |
C6A—C1A—C2A | 117.87 (15) | H83B—C83—H83C | 109.5 |
C6A—C1A—B1A | 121.82 (14) | C82'—C83—H83D | 109.5 |
C2A—C1A—B1A | 120.30 (14) | C82'—C83—H83E | 109.5 |
C3A—C2A—C1A | 119.49 (15) | H83D—C83—H83E | 109.5 |
C3A—C2A—C12A | 122.41 (14) | C82'—C83—H83F | 109.5 |
C1A—C2A—C12A | 118.10 (14) | H83D—C83—H83F | 109.5 |
C4A—C3A—C2A | 120.78 (16) | H83E—C83—H83F | 109.5 |
C11—O1—B1—F2 | 132.26 (16) | C11A—O1A—B1A—F2A | −95.67 (16) |
C11—O1—B1—F1 | −114.49 (17) | C11A—O1A—B1A—F1A | 150.16 (13) |
C11—O1—B1—C1 | 9.6 (2) | C11A—O1A—B1A—C1A | 27.71 (19) |
F2—B1—C1—C6 | 52.6 (2) | F2A—B1A—C1A—C6A | −76.55 (19) |
F1—B1—C1—C6 | −65.9 (2) | F1A—B1A—C1A—C6A | 43.0 (2) |
O1—B1—C1—C6 | 172.65 (14) | O1A—B1A—C1A—C6A | 161.88 (14) |
F2—B1—C1—C2 | −126.09 (15) | F2A—B1A—C1A—C2A | 102.47 (16) |
F1—B1—C1—C2 | 115.40 (16) | F1A—B1A—C1A—C2A | −138.00 (14) |
O1—B1—C1—C2 | −6.0 (2) | O1A—B1A—C1A—C2A | −19.10 (19) |
C6—C1—C2—C3 | −0.2 (2) | C6A—C1A—C2A—C3A | 0.4 (2) |
B1—C1—C2—C3 | 178.55 (14) | B1A—C1A—C2A—C3A | −178.69 (14) |
C6—C1—C2—C12 | −178.91 (13) | C6A—C1A—C2A—C12A | −179.02 (13) |
B1—C1—C2—C12 | −0.2 (2) | B1A—C1A—C2A—C12A | 1.9 (2) |
C1—C2—C3—C4 | −0.1 (2) | C1A—C2A—C3A—C4A | 0.0 (2) |
C12—C2—C3—C4 | 178.53 (14) | C12A—C2A—C3A—C4A | 179.37 (14) |
C2—C3—C4—C5 | 0.3 (2) | C2A—C3A—C4A—C5A | −0.3 (2) |
C3—C4—C5—C6 | −0.1 (2) | C3A—C4A—C5A—C6A | 0.2 (3) |
C4—C5—C6—C1 | −0.3 (3) | C4A—C5A—C6A—C1A | 0.2 (3) |
C2—C1—C6—C5 | 0.4 (2) | C2A—C1A—C6A—C5A | −0.5 (2) |
B1—C1—C6—C5 | −178.32 (15) | B1A—C1A—C6A—C5A | 178.56 (16) |
B1—O1—C11—C16 | 173.48 (16) | B1A—O1A—C11A—C16A | 161.76 (14) |
B1—O1—C11—C12 | −6.8 (2) | B1A—O1A—C11A—C12A | −19.1 (2) |
O1—C11—C12—C13 | −179.84 (14) | O1A—C11A—C12A—C13A | 179.16 (13) |
C16—C11—C12—C13 | −0.2 (2) | C16A—C11A—C12A—C13A | −1.7 (2) |
O1—C11—C12—C2 | −0.6 (2) | O1A—C11A—C12A—C2A | −1.2 (2) |
C16—C11—C12—C2 | 179.06 (14) | C16A—C11A—C12A—C2A | 177.91 (13) |
C3—C2—C12—C13 | 4.3 (2) | C3A—C2A—C12A—C13A | 9.5 (2) |
C1—C2—C12—C13 | −176.98 (14) | C1A—C2A—C12A—C13A | −171.16 (14) |
C3—C2—C12—C11 | −174.85 (14) | C3A—C2A—C12A—C11A | −170.15 (14) |
C1—C2—C12—C11 | 3.8 (2) | C1A—C2A—C12A—C11A | 9.2 (2) |
C11—C12—C13—C14 | 0.7 (2) | C11A—C12A—C13A—C14A | 0.8 (2) |
C2—C12—C13—C14 | −178.52 (14) | C2A—C12A—C13A—C14A | −178.82 (14) |
C12—C13—C14—C15 | −0.8 (2) | C12A—C13A—C14A—C15A | 0.5 (2) |
C13—C14—C15—C16 | 0.4 (3) | C13A—C14A—C15A—C16A | −0.8 (3) |
C14—C15—C16—C11 | 0.1 (3) | C14A—C15A—C16A—C11A | −0.2 (2) |
O1—C11—C16—C15 | 179.50 (16) | O1A—C11A—C16A—C15A | −179.37 (14) |
C12—C11—C16—C15 | −0.2 (3) | C12A—C11A—C16A—C15A | 1.5 (2) |
C51—P1—C21—C22 | 88.88 (14) | C31A—P1A—C21A—C22A | −107.92 (14) |
C31—P1—C21—C22 | −149.78 (12) | C51A—P1A—C21A—C22A | 10.75 (16) |
C41—P1—C21—C22 | −31.74 (14) | C41A—P1A—C21A—C22A | 129.78 (14) |
C51—P1—C21—C26 | −82.85 (13) | C31A—P1A—C21A—C26A | 69.37 (14) |
C31—P1—C21—C26 | 38.49 (14) | C51A—P1A—C21A—C26A | −171.96 (13) |
C41—P1—C21—C26 | 156.53 (12) | C41A—P1A—C21A—C26A | −52.93 (14) |
C26—C21—C22—C23 | −2.1 (2) | C26A—C21A—C22A—C23A | 0.3 (3) |
P1—C21—C22—C23 | −173.71 (13) | P1A—C21A—C22A—C23A | 177.55 (15) |
C21—C22—C23—C24 | 0.9 (3) | C21A—C22A—C23A—C24A | −1.1 (3) |
C22—C23—C24—C25 | 0.8 (3) | C22A—C23A—C24A—C25A | 0.7 (3) |
C23—C24—C25—C26 | −1.4 (3) | C23A—C24A—C25A—C26A | 0.6 (3) |
C24—C25—C26—C21 | 0.2 (3) | C24A—C25A—C26A—C21A | −1.4 (3) |
C22—C21—C26—C25 | 1.5 (2) | C22A—C21A—C26A—C25A | 1.0 (2) |
P1—C21—C26—C25 | 173.25 (12) | P1A—C21A—C26A—C25A | −176.32 (13) |
C51—P1—C31—C36 | −38.09 (14) | C21A—P1A—C31A—C36A | −14.99 (16) |
C41—P1—C31—C36 | 83.48 (13) | C51A—P1A—C31A—C36A | −133.78 (14) |
C21—P1—C31—C36 | −156.66 (11) | C41A—P1A—C31A—C36A | 104.73 (14) |
C51—P1—C31—C32 | 149.03 (12) | C21A—P1A—C31A—C32A | 164.34 (13) |
C41—P1—C31—C32 | −89.40 (13) | C51A—P1A—C31A—C32A | 45.56 (15) |
C21—P1—C31—C32 | 30.46 (14) | C41A—P1A—C31A—C32A | −75.94 (15) |
C36—C31—C32—C33 | 2.1 (2) | C36A—C31A—C32A—C33A | 0.8 (3) |
P1—C31—C32—C33 | 174.95 (12) | P1A—C31A—C32A—C33A | −178.57 (14) |
C31—C32—C33—C34 | −0.1 (2) | C31A—C32A—C33A—C34A | 1.2 (3) |
C32—C33—C34—C35 | −1.5 (2) | C32A—C33A—C34A—C35A | −2.0 (3) |
C33—C34—C35—C36 | 1.2 (2) | C33A—C34A—C35A—C36A | 0.8 (3) |
C34—C35—C36—C31 | 0.8 (2) | C34A—C35A—C36A—C31A | 1.2 (3) |
C32—C31—C36—C35 | −2.4 (2) | C32A—C31A—C36A—C35A | −1.9 (3) |
P1—C31—C36—C35 | −175.36 (11) | P1A—C31A—C36A—C35A | 177.39 (14) |
C51—P1—C41—C46 | 29.64 (15) | C21A—P1A—C41A—C42A | 157.16 (14) |
C31—P1—C41—C46 | −92.35 (13) | C31A—P1A—C41A—C42A | 37.13 (16) |
C21—P1—C41—C46 | 147.88 (12) | C51A—P1A—C41A—C42A | −84.04 (15) |
C51—P1—C41—C42 | −158.56 (12) | C21A—P1A—C41A—C46A | −26.78 (16) |
C31—P1—C41—C42 | 79.45 (14) | C31A—P1A—C41A—C46A | −146.80 (13) |
C21—P1—C41—C42 | −40.32 (14) | C51A—P1A—C41A—C46A | 92.02 (15) |
C46—C41—C42—C43 | −1.5 (2) | C46A—C41A—C42A—C43A | −0.1 (3) |
P1—C41—C42—C43 | −173.39 (13) | P1A—C41A—C42A—C43A | 175.99 (15) |
C41—C42—C43—C44 | 1.1 (3) | C41A—C42A—C43A—C44A | 0.1 (3) |
C42—C43—C44—C45 | 0.1 (3) | C42A—C43A—C44A—C45A | 0.3 (3) |
C43—C44—C45—C46 | −0.8 (3) | C43A—C44A—C45A—C46A | −0.7 (3) |
C44—C45—C46—C41 | 0.3 (2) | C44A—C45A—C46A—C41A | 0.7 (3) |
C42—C41—C46—C45 | 0.9 (2) | C42A—C41A—C46A—C45A | −0.4 (3) |
P1—C41—C46—C45 | 172.58 (12) | P1A—C41A—C46A—C45A | −176.43 (14) |
C31—P1—C51—C52 | 160.72 (12) | C21A—P1A—C51A—C56A | 91.18 (16) |
C41—P1—C51—C52 | 41.29 (14) | C31A—P1A—C51A—C56A | −150.29 (15) |
C21—P1—C51—C52 | −78.89 (13) | C41A—P1A—C51A—C56A | −27.04 (17) |
C31—P1—C51—C56 | −28.00 (14) | C21A—P1A—C51A—C52A | −83.80 (16) |
C41—P1—C51—C56 | −147.42 (12) | C31A—P1A—C51A—C52A | 34.73 (17) |
C21—P1—C51—C56 | 92.39 (13) | C41A—P1A—C51A—C52A | 157.98 (14) |
C56—C51—C52—C53 | 1.3 (2) | C56A—C51A—C52A—C53A | −0.3 (3) |
P1—C51—C52—C53 | 172.52 (12) | P1A—C51A—C52A—C53A | 174.66 (16) |
C51—C52—C53—C54 | −0.5 (2) | C51A—C52A—C53A—C54A | 0.3 (3) |
C52—C53—C54—C55 | −0.3 (2) | C52A—C53A—C54A—C55A | 0.2 (4) |
C53—C54—C55—C56 | 0.2 (2) | C53A—C54A—C55A—C56A | −0.5 (4) |
C54—C55—C56—C51 | 0.6 (2) | C52A—C51A—C56A—C55A | −0.1 (3) |
C52—C51—C56—C55 | −1.3 (2) | P1A—C51A—C56A—C55A | −175.04 (17) |
P1—C51—C56—C55 | −172.51 (12) | C54A—C55A—C56A—C51A | 0.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C26A—H26A···O1A | 0.95 | 2.58 | 3.322 (2) | 135 |
C32A—H32A···F2i | 0.95 | 2.40 | 3.069 (2) | 127 |
C42A—H42A···F2i | 0.95 | 2.51 | 3.378 (2) | 152 |
C44A—H44A···F1Ai | 0.95 | 2.54 | 3.482 (2) | 172 |
C53—H53···O1i | 0.95 | 2.59 | 3.389 (2) | 142 |
C54A—H54A···F2ii | 0.95 | 2.55 | 3.436 (3) | 156 |
C55A—H55A···N81′i | 0.95 | 2.52 | 3.180 (8) | 127 |
C63—H63A···N61iii | 0.98 | 2.58 | 3.365 (6) | 137 |
C63—H63C···N71iv | 0.98 | 2.47 | 3.371 (7) | 153 |
C73—H73A···F1 | 0.98 | 2.19 | 3.106 (4) | 156 |
C73—H73B···N81ii | 0.98 | 2.45 | 3.313 (10) | 146 |
C83—H83A···F1 | 0.98 | 2.52 | 3.252 (4) | 131 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+2, −z; (iv) x+1, y+1, z. |
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