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Three new chiral pyridine-containing oxazoline derivatives with fluorine and perfluoromethyl groups, namely, 2-({2-[(4
S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C
21H
16F
3N
3O, 2-({5-fluoro-2-[(4
S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C
18H
17F
4N
3O, and 2-({2-[(3a
R,8a
S)-8,8a-dihydro-3a
H-indeno[1,2-
d]oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C
22H
16F
3N
3O, as chiral ligands in metal-catalysed asymmetric reactions, were synthesized and characterized by spectral and X-ray diffraction methods. The conformation of the molecules is influenced by strong N—H
N hydrogen bonding and weak C—H
X (
X = O and N) interactions. There are no intermolecular hydrogen bonds in the crystal structures of the analysed compounds. Hirshfeld surface analysis showed that the H
H contacts constitute a high percentage of the intermolecular interactions. The conformational analysis was performed by theoretical calculations using the density functional theory (DFT) method. The mechanism of complex formation in terms of the electron-withdrawing effect of the substituents on the oxazoline ring and the ligand conformation is discussed.
Supporting information
CCDC references: 2102282; 2102281; 2102280
Data collection: CrysAlis PRO (Rigaku OD, 2019) for (5a), (5b); CrysAlis PRO (Agilent, 2015) for (5c). Cell refinement: CrysAlis PRO (Rigaku OD, 2019) for (5a), (5b); CrysAlis PRO (Agilent, 2015) for (5c). Data reduction: CrysAlis PRO (Rigaku OD, 2019) for (5a), (5b); CrysAlis PRO (Agilent, 2015) for (5c). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (5a); SHELXS2013 (Sheldrick, 2008) for (5b), (5c). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012).
2-({2-[(4
S)-4-Phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine (5a)
top
Crystal data top
C21H16F3N3O | Dx = 1.390 Mg m−3 |
Mr = 383.37 | Cu Kα radiation, λ = 1.54184 Å |
Trigonal, P31 | Cell parameters from 5131 reflections |
a = 17.1109 (4) Å | θ = 5.2–67.9° |
c = 5.4205 (2) Å | µ = 0.92 mm−1 |
V = 1374.41 (8) Å3 | T = 296 K |
Z = 3 | Prism, colourless |
F(000) = 594 | 0.10 × 0.05 × 0.05 mm |
Data collection top
XtaLAB AFC11 (RCD3): quarter-chi single diffractometer | 3142 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 2316 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.054 |
Detector resolution: 5.8140 pixels mm-1 | θmax = 68.5°, θmin = 5.2° |
ω scans | h = −20→20 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019) | k = −20→20 |
Tmin = 0.864, Tmax = 1.000 | l = −6→6 |
18179 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0749P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3142 reflections | Δρmax = 0.09 e Å−3 |
284 parameters | Δρmin = −0.12 e Å−3 |
13 restraints | Absolute structure: Flack x determined using 860 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (2) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F8A | 0.5453 (8) | 0.2941 (7) | 0.302 (3) | 0.134 (5) | 0.58 (3) |
F9A | 0.5537 (8) | 0.3453 (14) | 0.6626 (16) | 0.161 (5) | 0.58 (3) |
F10A | 0.5801 (8) | 0.4288 (6) | 0.349 (4) | 0.157 (5) | 0.58 (3) |
F8B | 0.5479 (13) | 0.325 (2) | 0.220 (4) | 0.198 (11) | 0.42 (3) |
F9B | 0.5284 (15) | 0.294 (2) | 0.606 (5) | 0.207 (10) | 0.42 (3) |
F10B | 0.5777 (11) | 0.4298 (9) | 0.475 (5) | 0.176 (10) | 0.42 (3) |
O19 | −0.06559 (17) | 0.2915 (2) | 0.3839 (7) | 0.1013 (9) | |
N1 | 0.2874 (2) | 0.2546 (2) | 0.2033 (6) | 0.0806 (8) | |
N11 | 0.1675 (2) | 0.2696 (2) | 0.3617 (6) | 0.0820 (9) | |
H11 | 0.151 (4) | 0.295 (4) | 0.480 (11) | 0.123* | |
N22 | 0.0686 (2) | 0.3349 (2) | 0.5615 (7) | 0.0878 (9) | |
C2 | 0.2543 (2) | 0.2843 (2) | 0.3777 (7) | 0.0732 (9) | |
C3 | 0.3048 (3) | 0.3323 (3) | 0.5854 (8) | 0.0844 (10) | |
H3 | 0.2791 | 0.3502 | 0.7080 | 0.127* | |
C4 | 0.3923 (3) | 0.3520 (3) | 0.6032 (9) | 0.0897 (11) | |
H4 | 0.4278 | 0.3852 | 0.7360 | 0.135* | |
C5 | 0.4279 (3) | 0.3218 (2) | 0.4206 (9) | 0.0842 (10) | |
C6 | 0.3728 (3) | 0.2737 (3) | 0.2297 (8) | 0.0858 (11) | |
H6 | 0.3964 | 0.2526 | 0.1092 | 0.129* | |
C7 | 0.5231 (4) | 0.3447 (3) | 0.4322 (11) | 0.1130 (17) | |
C12 | 0.0994 (2) | 0.2227 (2) | 0.1914 (7) | 0.0750 (9) | |
C13 | 0.0197 (2) | 0.2284 (2) | 0.2132 (8) | 0.0782 (9) | |
C14 | −0.0514 (3) | 0.1797 (3) | 0.0512 (9) | 0.0929 (12) | |
H14 | −0.1043 | 0.1818 | 0.0689 | 0.139* | |
C15 | −0.0451 (3) | 0.1283 (3) | −0.1354 (11) | 0.1024 (13) | |
H15 | −0.0927 | 0.0971 | −0.2448 | 0.154* | |
C16 | 0.0327 (3) | 0.1240 (3) | −0.1568 (10) | 0.0956 (12) | |
H16 | 0.0375 | 0.0898 | −0.2829 | 0.143* | |
C17 | 0.1034 (3) | 0.1690 (3) | 0.0034 (8) | 0.0846 (10) | |
H17 | 0.1547 | 0.1637 | −0.0135 | 0.127* | |
C18 | 0.0111 (2) | 0.2865 (3) | 0.3978 (8) | 0.0820 (11) | |
C20 | −0.0607 (3) | 0.3492 (4) | 0.5869 (12) | 0.1141 (17) | |
H201 | −0.1051 | 0.3146 | 0.7124 | 0.171* | |
H202 | −0.0710 | 0.3970 | 0.5291 | 0.171* | |
C21 | 0.0347 (3) | 0.3881 (3) | 0.6883 (9) | 0.0901 (11) | |
H21 | 0.0316 | 0.3763 | 0.8659 | 0.135* | |
C23 | 0.0953 (2) | 0.4881 (3) | 0.6432 (7) | 0.0765 (9) | |
C24 | 0.1515 (3) | 0.5212 (3) | 0.4420 (8) | 0.0909 (11) | |
H24 | 0.1523 | 0.4810 | 0.3280 | 0.136* | |
C25 | 0.2063 (3) | 0.6119 (3) | 0.4053 (10) | 0.0996 (13) | |
H25 | 0.2439 | 0.6326 | 0.2680 | 0.149* | |
C26 | 0.2060 (3) | 0.6724 (3) | 0.5703 (11) | 0.0994 (13) | |
H26 | 0.2434 | 0.7341 | 0.5463 | 0.149* | |
C27 | 0.1503 (3) | 0.6413 (3) | 0.7697 (10) | 0.1011 (14) | |
H27 | 0.1497 | 0.6821 | 0.8819 | 0.152* | |
C28 | 0.0946 (3) | 0.5497 (3) | 0.8076 (9) | 0.0905 (11) | |
H28 | 0.0564 | 0.5294 | 0.9439 | 0.136* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F8A | 0.092 (4) | 0.120 (6) | 0.210 (12) | 0.069 (4) | −0.017 (5) | −0.038 (5) |
F9A | 0.099 (5) | 0.218 (13) | 0.158 (7) | 0.073 (7) | −0.034 (4) | 0.003 (7) |
F10A | 0.085 (4) | 0.105 (6) | 0.272 (15) | 0.041 (4) | 0.034 (7) | 0.037 (7) |
F8B | 0.105 (8) | 0.31 (3) | 0.201 (14) | 0.126 (15) | −0.007 (8) | −0.057 (16) |
F9B | 0.151 (13) | 0.26 (2) | 0.27 (3) | 0.149 (15) | −0.048 (13) | 0.019 (17) |
F10B | 0.071 (6) | 0.168 (15) | 0.24 (2) | 0.024 (7) | −0.013 (9) | −0.091 (15) |
O19 | 0.0663 (15) | 0.0931 (18) | 0.145 (3) | 0.0398 (13) | 0.0077 (15) | −0.0022 (18) |
N1 | 0.0729 (17) | 0.0756 (17) | 0.095 (2) | 0.0385 (15) | 0.0045 (15) | −0.0026 (15) |
N11 | 0.0749 (19) | 0.0826 (19) | 0.091 (2) | 0.0411 (16) | −0.0019 (15) | −0.0060 (16) |
N22 | 0.0820 (19) | 0.0799 (19) | 0.112 (3) | 0.0481 (16) | 0.0033 (19) | −0.0014 (18) |
C2 | 0.0714 (19) | 0.0621 (18) | 0.087 (2) | 0.0339 (16) | 0.0025 (18) | 0.0055 (17) |
C3 | 0.086 (2) | 0.079 (2) | 0.090 (3) | 0.043 (2) | −0.0012 (19) | −0.0044 (19) |
C4 | 0.080 (2) | 0.080 (2) | 0.106 (3) | 0.0372 (19) | −0.011 (2) | −0.006 (2) |
C5 | 0.074 (2) | 0.0679 (19) | 0.111 (3) | 0.0350 (18) | −0.002 (2) | 0.003 (2) |
C6 | 0.077 (2) | 0.076 (2) | 0.106 (3) | 0.0394 (19) | 0.007 (2) | 0.001 (2) |
C7 | 0.087 (3) | 0.109 (4) | 0.152 (5) | 0.056 (3) | −0.002 (3) | −0.007 (3) |
C12 | 0.069 (2) | 0.0650 (17) | 0.087 (2) | 0.0302 (15) | 0.0050 (17) | 0.0103 (16) |
C13 | 0.0675 (19) | 0.0669 (18) | 0.095 (2) | 0.0297 (16) | 0.0052 (18) | 0.0116 (18) |
C14 | 0.071 (2) | 0.079 (2) | 0.119 (3) | 0.0296 (19) | 0.000 (2) | 0.008 (2) |
C15 | 0.080 (3) | 0.087 (3) | 0.118 (4) | 0.026 (2) | −0.009 (2) | −0.002 (3) |
C16 | 0.085 (3) | 0.080 (2) | 0.106 (3) | 0.030 (2) | −0.002 (2) | −0.004 (2) |
C17 | 0.080 (2) | 0.074 (2) | 0.095 (3) | 0.0350 (18) | 0.003 (2) | −0.0007 (19) |
C18 | 0.064 (2) | 0.072 (2) | 0.112 (3) | 0.0347 (17) | 0.014 (2) | 0.016 (2) |
C20 | 0.077 (3) | 0.092 (3) | 0.175 (5) | 0.044 (2) | 0.018 (3) | −0.003 (3) |
C21 | 0.082 (2) | 0.085 (2) | 0.113 (3) | 0.050 (2) | 0.016 (2) | 0.009 (2) |
C23 | 0.071 (2) | 0.084 (2) | 0.086 (2) | 0.0469 (18) | 0.0035 (17) | 0.0021 (18) |
C24 | 0.089 (3) | 0.091 (3) | 0.091 (3) | 0.044 (2) | 0.012 (2) | 0.002 (2) |
C25 | 0.088 (3) | 0.099 (3) | 0.101 (3) | 0.039 (2) | 0.009 (2) | 0.013 (3) |
C26 | 0.084 (3) | 0.084 (3) | 0.121 (4) | 0.035 (2) | −0.011 (3) | 0.006 (3) |
C27 | 0.100 (3) | 0.091 (3) | 0.122 (4) | 0.056 (3) | −0.003 (3) | −0.012 (3) |
C28 | 0.084 (2) | 0.097 (3) | 0.101 (3) | 0.053 (2) | 0.012 (2) | 0.001 (2) |
Geometric parameters (Å, º) top
F8A—C7 | 1.312 (9) | C13—C14 | 1.389 (6) |
F9A—C7 | 1.352 (9) | C13—C18 | 1.469 (6) |
F10A—C7 | 1.349 (9) | C14—C15 | 1.379 (7) |
F8B—C7 | 1.329 (11) | C14—H14 | 0.9300 |
F9B—C7 | 1.313 (11) | C15—C16 | 1.374 (7) |
F10B—C7 | 1.298 (11) | C15—H15 | 0.9300 |
O19—C18 | 1.360 (5) | C16—C17 | 1.371 (6) |
O19—C20 | 1.453 (6) | C16—H16 | 0.9300 |
N1—C2 | 1.326 (5) | C17—H17 | 0.9300 |
N1—C6 | 1.336 (5) | C20—C21 | 1.524 (7) |
N11—C2 | 1.379 (5) | C20—H201 | 0.9700 |
N11—C12 | 1.385 (5) | C20—H202 | 0.9700 |
N11—H11 | 0.90 (6) | C21—C23 | 1.512 (6) |
N22—C18 | 1.275 (5) | C21—H21 | 0.9800 |
N22—C21 | 1.472 (5) | C23—C24 | 1.375 (6) |
C2—C3 | 1.407 (6) | C23—C28 | 1.386 (6) |
C3—C4 | 1.364 (6) | C24—C25 | 1.369 (7) |
C3—H3 | 0.9300 | C24—H24 | 0.9300 |
C4—C5 | 1.390 (6) | C25—C26 | 1.370 (7) |
C4—H4 | 0.9300 | C25—H25 | 0.9300 |
C5—C6 | 1.364 (6) | C26—C27 | 1.361 (7) |
C5—C7 | 1.473 (7) | C26—H26 | 0.9300 |
C6—H6 | 0.9300 | C27—C28 | 1.383 (6) |
C12—C17 | 1.396 (6) | C27—H27 | 0.9300 |
C12—C13 | 1.421 (5) | C28—H28 | 0.9300 |
| | | |
C18—O19—C20 | 105.8 (3) | C16—C15—C14 | 118.8 (5) |
C2—N1—C6 | 117.1 (3) | C16—C15—H15 | 120.6 |
C2—N11—C12 | 131.6 (4) | C14—C15—H15 | 120.6 |
C2—N11—H11 | 116 (4) | C17—C16—C15 | 121.6 (5) |
C12—N11—H11 | 113 (4) | C17—C16—H16 | 119.2 |
C18—N22—C21 | 108.2 (3) | C15—C16—H16 | 119.2 |
N1—C2—N11 | 120.8 (3) | C16—C17—C12 | 120.8 (4) |
N1—C2—C3 | 122.6 (3) | C16—C17—H17 | 119.6 |
N11—C2—C3 | 116.6 (3) | C12—C17—H17 | 119.6 |
C4—C3—C2 | 118.6 (4) | N22—C18—O19 | 116.9 (4) |
C4—C3—H3 | 120.7 | N22—C18—C13 | 127.5 (3) |
C2—C3—H3 | 120.7 | O19—C18—C13 | 115.5 (4) |
C3—C4—C5 | 119.3 (4) | O19—C20—C21 | 104.8 (3) |
C3—C4—H4 | 120.4 | O19—C20—H201 | 110.8 |
C5—C4—H4 | 120.4 | C21—C20—H201 | 110.8 |
C6—C5—C4 | 117.7 (4) | O19—C20—H202 | 110.8 |
C6—C5—C7 | 122.1 (4) | C21—C20—H202 | 110.8 |
C4—C5—C7 | 120.1 (4) | H201—C20—H202 | 108.9 |
N1—C6—C5 | 124.7 (4) | N22—C21—C23 | 111.4 (3) |
N1—C6—H6 | 117.6 | N22—C21—C20 | 103.2 (4) |
C5—C6—H6 | 117.6 | C23—C21—C20 | 114.5 (4) |
F10B—C7—F9B | 111.3 (11) | N22—C21—H21 | 109.2 |
F10B—C7—F8B | 107.3 (10) | C23—C21—H21 | 109.2 |
F9B—C7—F8B | 108.5 (10) | C20—C21—H21 | 109.2 |
F8A—C7—F10A | 103.4 (8) | C24—C23—C28 | 117.8 (4) |
F8A—C7—F9A | 105.1 (8) | C24—C23—C21 | 122.5 (4) |
F10A—C7—F9A | 103.2 (8) | C28—C23—C21 | 119.7 (4) |
F10B—C7—C5 | 112.8 (9) | C25—C24—C23 | 121.6 (4) |
F9B—C7—C5 | 106.6 (9) | C25—C24—H24 | 119.2 |
F8A—C7—C5 | 116.6 (6) | C23—C24—H24 | 119.2 |
F8B—C7—C5 | 110.3 (10) | C24—C25—C26 | 120.2 (5) |
F10A—C7—C5 | 112.6 (6) | C24—C25—H25 | 119.9 |
F9A—C7—C5 | 114.5 (7) | C26—C25—H25 | 119.9 |
N11—C12—C17 | 124.4 (3) | C27—C26—C25 | 119.3 (4) |
N11—C12—C13 | 117.6 (4) | C27—C26—H26 | 120.3 |
C17—C12—C13 | 118.0 (4) | C25—C26—H26 | 120.3 |
C14—C13—C12 | 119.3 (4) | C26—C27—C28 | 120.8 (5) |
C14—C13—C18 | 118.9 (3) | C26—C27—H27 | 119.6 |
C12—C13—C18 | 121.8 (4) | C28—C27—H27 | 119.6 |
C15—C14—C13 | 121.5 (4) | C27—C28—C23 | 120.2 (4) |
C15—C14—H14 | 119.3 | C27—C28—H28 | 119.9 |
C13—C14—H14 | 119.3 | C23—C28—H28 | 119.9 |
| | | |
C6—N1—C2—N11 | 178.3 (3) | C18—C13—C14—C15 | 176.1 (4) |
C6—N1—C2—C3 | −1.2 (5) | C13—C14—C15—C16 | 1.4 (7) |
C12—N11—C2—N1 | 3.5 (6) | C14—C15—C16—C17 | 0.4 (7) |
C12—N11—C2—C3 | −177.0 (4) | C15—C16—C17—C12 | −1.5 (7) |
N1—C2—C3—C4 | 2.5 (6) | N11—C12—C17—C16 | 179.4 (4) |
N11—C2—C3—C4 | −177.0 (3) | C13—C12—C17—C16 | 0.7 (6) |
C2—C3—C4—C5 | −2.0 (6) | C21—N22—C18—O19 | −2.5 (5) |
C3—C4—C5—C6 | 0.3 (6) | C21—N22—C18—C13 | 174.5 (4) |
C3—C4—C5—C7 | 178.1 (4) | C20—O19—C18—N22 | −4.6 (5) |
C2—N1—C6—C5 | −0.7 (6) | C20—O19—C18—C13 | 178.0 (4) |
C4—C5—C6—N1 | 1.1 (6) | C14—C13—C18—N22 | 179.2 (4) |
C7—C5—C6—N1 | −176.6 (4) | C12—C13—C18—N22 | −2.6 (6) |
C6—C5—C7—F10B | 129.7 (15) | C14—C13—C18—O19 | −3.7 (5) |
C4—C5—C7—F10B | −48.0 (16) | C12—C13—C18—O19 | 174.4 (3) |
C6—C5—C7—F9B | −107.8 (18) | C18—O19—C20—C21 | 9.2 (5) |
C4—C5—C7—F9B | 74.5 (18) | C18—N22—C21—C23 | −115.3 (4) |
C6—C5—C7—F8A | −21.9 (10) | C18—N22—C21—C20 | 8.0 (5) |
C4—C5—C7—F8A | 160.4 (9) | O19—C20—C21—N22 | −10.3 (5) |
C6—C5—C7—F8B | 9.8 (18) | O19—C20—C21—C23 | 111.0 (4) |
C4—C5—C7—F8B | −167.9 (17) | N22—C21—C23—C24 | 23.2 (6) |
C6—C5—C7—F10A | 97.3 (12) | C20—C21—C23—C24 | −93.5 (5) |
C4—C5—C7—F10A | −80.4 (12) | N22—C21—C23—C28 | −157.5 (4) |
C6—C5—C7—F9A | −145.2 (11) | C20—C21—C23—C28 | 85.9 (5) |
C4—C5—C7—F9A | 37.1 (12) | C28—C23—C24—C25 | 1.1 (6) |
C2—N11—C12—C17 | 7.9 (6) | C21—C23—C24—C25 | −179.6 (4) |
C2—N11—C12—C13 | −173.4 (4) | C23—C24—C25—C26 | −0.3 (7) |
N11—C12—C13—C14 | −177.8 (3) | C24—C25—C26—C27 | −0.4 (7) |
C17—C12—C13—C14 | 1.1 (5) | C25—C26—C27—C28 | 0.2 (7) |
N11—C12—C13—C18 | 4.1 (5) | C26—C27—C28—C23 | 0.6 (7) |
C17—C12—C13—C18 | −177.1 (3) | C24—C23—C28—C27 | −1.2 (6) |
C12—C13—C14—C15 | −2.1 (6) | C21—C23—C28—C27 | 179.4 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···N22 | 0.90 (7) | 1.90 (7) | 2.681 (5) | 144 (6) |
C14—H14···O19 | 0.93 | 2.37 | 2.727 (6) | 102 |
C17—H17···N1 | 0.93 | 2.33 | 2.936 (6) | 123 |
C24—H24···N22 | 0.93 | 2.51 | 2.841 (5) | 101 |
2-({5-Fluoro-2-[(4
S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine (5b)
top
Crystal data top
C18H17F4N3O | F(000) = 760 |
Mr = 367.34 | Dx = 1.426 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.9933 (2) Å | Cell parameters from 6225 reflections |
b = 24.1126 (5) Å | θ = 5.0–67.9° |
c = 9.1926 (2) Å | µ = 1.04 mm−1 |
β = 105.003 (2)° | T = 296 K |
V = 1711.38 (7) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.10 × 0.05 mm |
Data collection top
XtaLAB AFC11 (RCD3): quarter-chi single diffractometer | 5663 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 4961 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.059 |
Detector resolution: 5.8140 pixels mm-1 | θmax = 68.3°, θmin = 5.0° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019) | k = −29→28 |
Tmin = 0.419, Tmax = 1.000 | l = −11→11 |
11889 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0964P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5663 reflections | Δρmax = 0.18 e Å−3 |
535 parameters | Δρmin = −0.17 e Å−3 |
193 restraints | Absolute structure: Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (10) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C2A | 0.2797 (5) | 0.28310 (15) | 0.2087 (4) | 0.0563 (8) | |
C3A | 0.3859 (6) | 0.30300 (18) | 0.3458 (5) | 0.0715 (10) | |
H3A | 0.4124 | 0.2804 | 0.4306 | 0.107* | |
C4A | 0.4495 (6) | 0.35565 (18) | 0.3532 (5) | 0.0714 (10) | |
H4A | 0.5193 | 0.3695 | 0.4429 | 0.107* | |
C5A | 0.4078 (5) | 0.38847 (17) | 0.2235 (4) | 0.0605 (8) | |
C6A | 0.3122 (5) | 0.36468 (17) | 0.0938 (4) | 0.0645 (9) | |
H6A | 0.2898 | 0.3858 | 0.0062 | 0.097* | |
C7A | 0.4651 (5) | 0.44674 (18) | 0.2299 (4) | 0.0698 (10) | |
C12A | 0.0981 (5) | 0.20001 (15) | 0.1025 (4) | 0.0558 (8) | |
C13A | 0.0600 (5) | 0.14544 (16) | 0.1407 (4) | 0.0568 (8) | |
C14A | −0.0536 (5) | 0.11277 (16) | 0.0341 (4) | 0.0633 (9) | |
H14A | −0.0792 | 0.0768 | 0.0578 | 0.095* | |
C15A | −0.1267 (5) | 0.13403 (18) | −0.1049 (5) | 0.0673 (9) | |
C16A | −0.0964 (5) | 0.18735 (18) | −0.1451 (4) | 0.0674 (9) | |
H16A | −0.1505 | 0.2010 | −0.2403 | 0.101* | |
C17A | 0.0155 (6) | 0.21990 (18) | −0.0412 (4) | 0.0677 (9) | |
H17A | 0.0370 | 0.2560 | −0.0669 | 0.102* | |
C18A | 0.1308 (5) | 0.12250 (16) | 0.2924 (4) | 0.0578 (8) | |
C20A | 0.1488 (7) | 0.05827 (19) | 0.4715 (5) | 0.0778 (11) | |
H20A | 0.2142 | 0.0239 | 0.4852 | 0.117* | |
H20B | 0.0573 | 0.0553 | 0.5227 | 0.117* | |
C21A | 0.2681 (6) | 0.10816 (16) | 0.5318 (4) | 0.0645 (9) | |
H21A | 0.3889 | 0.0959 | 0.5531 | 0.097* | |
C23A | 0.2381 (5) | 0.13503 (18) | 0.6732 (4) | 0.0670 (9) | |
H23A | 0.1163 | 0.1464 | 0.6513 | 0.100* | |
C24A | 0.3496 (7) | 0.1864 (2) | 0.7185 (5) | 0.0854 (13) | |
H24A | 0.3201 | 0.2134 | 0.6393 | 0.128* | |
H24B | 0.4695 | 0.1765 | 0.7359 | 0.128* | |
H24C | 0.3297 | 0.2016 | 0.8090 | 0.128* | |
C25A | 0.2718 (7) | 0.0929 (2) | 0.8020 (5) | 0.0813 (12) | |
H25A | 0.1974 | 0.0614 | 0.7724 | 0.122* | |
H25B | 0.2488 | 0.1098 | 0.8895 | 0.122* | |
H25C | 0.3905 | 0.0812 | 0.8251 | 0.122* | |
N1A | 0.2480 (4) | 0.31285 (14) | 0.0837 (3) | 0.0632 (8) | |
N11A | 0.2134 (4) | 0.23083 (14) | 0.2118 (4) | 0.0641 (8) | |
H11A | 0.254 (7) | 0.212 (3) | 0.313 (6) | 0.096* | |
N22A | 0.2335 (4) | 0.14645 (14) | 0.4031 (3) | 0.0638 (8) | |
O19A | 0.0786 (4) | 0.06997 (11) | 0.3143 (3) | 0.0697 (7) | |
F8A | 0.6352 (13) | 0.4557 (8) | 0.250 (3) | 0.117 (5) | 0.48 (4) |
F9A | 0.423 (3) | 0.4738 (9) | 0.3409 (19) | 0.093 (4) | 0.48 (4) |
F10A | 0.387 (3) | 0.4739 (8) | 0.1046 (16) | 0.111 (5) | 0.48 (4) |
F9C | 0.385 (2) | 0.4796 (8) | 0.306 (3) | 0.101 (4) | 0.52 (4) |
F10C | 0.455 (4) | 0.4697 (9) | 0.0986 (11) | 0.133 (6) | 0.52 (4) |
F8C | 0.6342 (11) | 0.4499 (6) | 0.304 (2) | 0.096 (4) | 0.52 (4) |
F15A | −0.2372 (4) | 0.10138 (13) | −0.2099 (3) | 0.0935 (8) | |
C2B | 0.7664 (5) | 0.23216 (14) | 0.2988 (4) | 0.0545 (7) | |
C3B | 0.6662 (5) | 0.21215 (16) | 0.1602 (4) | 0.0613 (8) | |
H3B | 0.6413 | 0.2348 | 0.0754 | 0.092* | |
C4B | 0.6058 (5) | 0.15880 (16) | 0.1517 (4) | 0.0639 (9) | |
H4B | 0.5399 | 0.1445 | 0.0610 | 0.096* | |
C5B | 0.6448 (5) | 0.12635 (15) | 0.2818 (4) | 0.0584 (8) | |
C6B | 0.7352 (6) | 0.15046 (17) | 0.4124 (4) | 0.0682 (10) | |
H6B | 0.7556 | 0.1293 | 0.4998 | 0.102* | |
C7B | 0.5889 (5) | 0.06767 (17) | 0.2741 (4) | 0.0688 (10) | |
C12B | 0.9337 (4) | 0.31726 (15) | 0.4108 (4) | 0.0551 (8) | |
C13B | 0.9789 (4) | 0.37141 (15) | 0.3713 (4) | 0.0537 (7) | |
C14B | 1.0767 (5) | 0.40598 (15) | 0.4815 (4) | 0.0612 (8) | |
H14B | 1.1053 | 0.4415 | 0.4566 | 0.092* | |
C15B | 1.1312 (5) | 0.38770 (16) | 0.6269 (4) | 0.0650 (9) | |
C16B | 1.0953 (6) | 0.33511 (17) | 0.6681 (4) | 0.0678 (10) | |
H16B | 1.1371 | 0.3231 | 0.7670 | 0.102* | |
C17B | 0.9959 (5) | 0.30031 (16) | 0.5601 (4) | 0.0625 (9) | |
H17B | 0.9700 | 0.2648 | 0.5876 | 0.094* | |
C18B | 0.9321 (5) | 0.39068 (15) | 0.2142 (4) | 0.0558 (8) | |
C20B | 0.9178 (7) | 0.45317 (17) | 0.0318 (5) | 0.0743 (11) | |
H20C | 1.0075 | 0.4671 | −0.0123 | 0.111* | |
H20D | 0.8242 | 0.4800 | 0.0147 | 0.111* | |
C21B | 0.8518 (5) | 0.39655 (16) | −0.0347 (4) | 0.0636 (9) | |
H21B | 0.9371 | 0.3810 | −0.0830 | 0.095* | |
C23B | 0.6767 (6) | 0.39771 (17) | −0.1500 (4) | 0.0676 (9) | |
H23B | 0.5931 | 0.4153 | −0.1033 | 0.101* | |
C24B | 0.6125 (8) | 0.3398 (2) | −0.1983 (5) | 0.0885 (14) | |
H24D | 0.6899 | 0.3223 | −0.2486 | 0.133* | |
H24E | 0.4987 | 0.3419 | −0.2656 | 0.133* | |
H24F | 0.6082 | 0.3184 | −0.1112 | 0.133* | |
C25B | 0.6886 (7) | 0.4324 (2) | −0.2843 (5) | 0.0819 (12) | |
H25D | 0.7362 | 0.4681 | −0.2503 | 0.123* | |
H25E | 0.5750 | 0.4370 | −0.3506 | 0.123* | |
H25F | 0.7620 | 0.4141 | −0.3370 | 0.123* | |
N1B | 0.7969 (5) | 0.20236 (13) | 0.4249 (3) | 0.0636 (8) | |
N11B | 0.8311 (4) | 0.28483 (13) | 0.2971 (4) | 0.0610 (7) | |
H11B | 0.815 (7) | 0.305 (3) | 0.206 (6) | 0.092* | |
N22B | 0.8525 (5) | 0.36291 (13) | 0.0990 (3) | 0.0624 (7) | |
O19B | 0.9865 (4) | 0.44237 (11) | 0.1914 (3) | 0.0684 (7) | |
F8B | 0.648 (3) | 0.0396 (7) | 0.4018 (10) | 0.126 (5) | 0.61 (4) |
F9B | 0.6548 (15) | 0.0396 (4) | 0.1766 (14) | 0.086 (3) | 0.61 (4) |
F10B | 0.4199 (10) | 0.0598 (6) | 0.230 (2) | 0.121 (4) | 0.61 (4) |
F8D | 0.582 (4) | 0.0490 (12) | 0.4063 (15) | 0.109 (6) | 0.39 (4) |
F9D | 0.682 (3) | 0.0322 (9) | 0.218 (3) | 0.132 (8) | 0.39 (4) |
F10D | 0.4258 (18) | 0.0636 (9) | 0.183 (2) | 0.105 (5) | 0.39 (4) |
F15B | 1.2263 (4) | 0.42163 (11) | 0.7340 (3) | 0.0956 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2A | 0.0641 (18) | 0.0471 (19) | 0.0535 (18) | 0.0007 (16) | 0.0077 (14) | −0.0017 (15) |
C3A | 0.093 (3) | 0.058 (2) | 0.054 (2) | −0.006 (2) | 0.0022 (18) | 0.0044 (18) |
C4A | 0.091 (3) | 0.060 (2) | 0.054 (2) | −0.009 (2) | 0.0033 (19) | −0.0044 (17) |
C5A | 0.076 (2) | 0.050 (2) | 0.0525 (19) | −0.0037 (17) | 0.0125 (16) | −0.0045 (15) |
C6A | 0.082 (2) | 0.050 (2) | 0.056 (2) | −0.0094 (19) | 0.0088 (17) | 0.0031 (16) |
C7A | 0.085 (2) | 0.055 (2) | 0.064 (2) | −0.009 (2) | 0.0107 (18) | −0.0067 (19) |
C12A | 0.0676 (18) | 0.0461 (18) | 0.0511 (18) | −0.0012 (16) | 0.0109 (15) | −0.0002 (14) |
C13A | 0.0682 (17) | 0.0457 (18) | 0.0561 (19) | 0.0023 (17) | 0.0152 (15) | 0.0008 (15) |
C14A | 0.078 (2) | 0.047 (2) | 0.065 (2) | −0.0028 (17) | 0.0176 (18) | −0.0027 (16) |
C15A | 0.075 (2) | 0.059 (2) | 0.063 (2) | −0.0117 (19) | 0.0089 (17) | −0.0108 (17) |
C16A | 0.081 (2) | 0.061 (2) | 0.054 (2) | −0.004 (2) | 0.0064 (17) | 0.0046 (17) |
C17A | 0.082 (2) | 0.055 (2) | 0.061 (2) | −0.0091 (19) | 0.0084 (17) | 0.0037 (17) |
C18A | 0.0707 (18) | 0.0412 (18) | 0.064 (2) | 0.0068 (17) | 0.0211 (17) | 0.0022 (16) |
C20A | 0.109 (3) | 0.052 (2) | 0.068 (2) | −0.001 (2) | 0.016 (2) | 0.0075 (19) |
C21A | 0.079 (2) | 0.050 (2) | 0.062 (2) | 0.0098 (17) | 0.0142 (17) | 0.0082 (16) |
C23A | 0.078 (2) | 0.062 (2) | 0.0565 (19) | 0.0138 (19) | 0.0102 (16) | 0.0034 (17) |
C24A | 0.110 (3) | 0.067 (3) | 0.071 (3) | −0.001 (3) | 0.008 (2) | −0.007 (2) |
C25A | 0.105 (3) | 0.076 (3) | 0.059 (2) | 0.004 (3) | 0.014 (2) | 0.013 (2) |
N1A | 0.0810 (18) | 0.0517 (18) | 0.0494 (16) | −0.0096 (15) | 0.0035 (13) | 0.0011 (13) |
N11A | 0.0804 (19) | 0.0503 (17) | 0.0535 (17) | −0.0095 (16) | 0.0026 (14) | 0.0050 (14) |
N22A | 0.0846 (19) | 0.0504 (17) | 0.0542 (16) | 0.0003 (16) | 0.0141 (15) | 0.0032 (13) |
O19A | 0.0941 (18) | 0.0450 (14) | 0.0661 (15) | −0.0025 (14) | 0.0137 (13) | 0.0062 (12) |
F8A | 0.094 (5) | 0.066 (5) | 0.200 (15) | −0.006 (5) | 0.057 (6) | 0.006 (8) |
F9A | 0.131 (9) | 0.065 (7) | 0.082 (6) | 0.007 (5) | 0.023 (6) | −0.017 (4) |
F10A | 0.163 (11) | 0.060 (5) | 0.088 (6) | −0.031 (7) | −0.008 (5) | 0.021 (4) |
F9C | 0.113 (7) | 0.047 (5) | 0.146 (10) | −0.002 (5) | 0.040 (7) | −0.013 (7) |
F10C | 0.233 (16) | 0.087 (8) | 0.068 (5) | −0.072 (10) | 0.022 (6) | −0.001 (4) |
F8C | 0.080 (4) | 0.071 (5) | 0.128 (9) | −0.036 (4) | 0.008 (4) | −0.006 (5) |
F15A | 0.115 (2) | 0.0773 (18) | 0.0728 (15) | −0.0285 (15) | −0.0045 (14) | −0.0077 (13) |
C2B | 0.0659 (18) | 0.0393 (17) | 0.0558 (18) | 0.0017 (16) | 0.0115 (14) | 0.0000 (15) |
C3B | 0.080 (2) | 0.0445 (18) | 0.0525 (18) | −0.0030 (17) | 0.0056 (16) | 0.0030 (15) |
C4B | 0.078 (2) | 0.052 (2) | 0.056 (2) | −0.0093 (18) | 0.0068 (17) | −0.0057 (16) |
C5B | 0.0728 (19) | 0.0413 (18) | 0.062 (2) | −0.0028 (17) | 0.0185 (16) | −0.0034 (16) |
C6B | 0.094 (3) | 0.047 (2) | 0.059 (2) | −0.008 (2) | 0.0114 (19) | 0.0039 (17) |
C7B | 0.088 (2) | 0.048 (2) | 0.071 (2) | −0.008 (2) | 0.0226 (19) | −0.0052 (18) |
C12B | 0.0657 (18) | 0.0411 (18) | 0.0555 (19) | −0.0026 (16) | 0.0102 (15) | −0.0007 (15) |
C13B | 0.0643 (17) | 0.0422 (17) | 0.0515 (17) | 0.0006 (15) | 0.0093 (14) | 0.0012 (14) |
C14B | 0.074 (2) | 0.0423 (18) | 0.061 (2) | −0.0055 (17) | 0.0061 (16) | −0.0023 (15) |
C15B | 0.084 (2) | 0.049 (2) | 0.0533 (19) | −0.0074 (18) | 0.0007 (16) | −0.0059 (16) |
C16B | 0.089 (2) | 0.054 (2) | 0.0514 (19) | −0.007 (2) | 0.0023 (18) | 0.0000 (16) |
C17B | 0.081 (2) | 0.048 (2) | 0.0537 (19) | −0.0052 (18) | 0.0076 (16) | 0.0019 (16) |
C18B | 0.0668 (18) | 0.0427 (18) | 0.0557 (19) | −0.0006 (15) | 0.0120 (15) | 0.0031 (14) |
C20B | 0.104 (3) | 0.050 (2) | 0.062 (2) | −0.007 (2) | 0.009 (2) | 0.0127 (18) |
C21B | 0.082 (2) | 0.0499 (19) | 0.0554 (19) | 0.0019 (18) | 0.0112 (16) | 0.0064 (15) |
C23B | 0.082 (2) | 0.055 (2) | 0.060 (2) | 0.0078 (19) | 0.0071 (17) | 0.0019 (17) |
C24B | 0.110 (3) | 0.070 (3) | 0.072 (3) | −0.013 (3) | −0.002 (3) | 0.007 (2) |
C25B | 0.114 (3) | 0.061 (3) | 0.063 (2) | 0.012 (2) | 0.008 (2) | 0.0078 (19) |
N1B | 0.087 (2) | 0.0414 (16) | 0.0548 (17) | −0.0078 (15) | 0.0052 (14) | 0.0015 (13) |
N11B | 0.0827 (19) | 0.0410 (16) | 0.0515 (16) | −0.0096 (15) | 0.0033 (14) | 0.0022 (13) |
N22B | 0.0866 (19) | 0.0421 (15) | 0.0525 (16) | −0.0034 (15) | 0.0068 (14) | 0.0029 (12) |
O19B | 0.0866 (16) | 0.0476 (13) | 0.0624 (15) | −0.0142 (13) | 0.0038 (12) | 0.0088 (12) |
F8B | 0.233 (14) | 0.049 (5) | 0.085 (4) | −0.027 (7) | 0.020 (5) | 0.008 (3) |
F9B | 0.128 (5) | 0.034 (3) | 0.104 (5) | −0.010 (3) | 0.047 (4) | −0.020 (3) |
F10B | 0.090 (4) | 0.059 (4) | 0.230 (13) | −0.018 (4) | 0.070 (6) | −0.001 (6) |
F8D | 0.189 (14) | 0.056 (10) | 0.091 (6) | −0.024 (8) | 0.054 (7) | 0.006 (5) |
F9D | 0.148 (11) | 0.070 (8) | 0.204 (18) | 0.018 (7) | 0.093 (13) | 0.012 (9) |
F10D | 0.094 (7) | 0.079 (7) | 0.122 (9) | −0.046 (6) | −0.012 (7) | 0.013 (6) |
F15B | 0.138 (2) | 0.0643 (16) | 0.0638 (13) | −0.0315 (16) | −0.0103 (14) | −0.0046 (12) |
Geometric parameters (Å, º) top
C2A—N1A | 1.322 (5) | C2B—N1B | 1.331 (5) |
C2A—N11A | 1.370 (5) | C2B—N11B | 1.373 (5) |
C2A—C3A | 1.409 (6) | C2B—C3B | 1.403 (5) |
C3A—C4A | 1.363 (6) | C3B—C4B | 1.369 (5) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.398 (6) | C4B—C5B | 1.395 (5) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.365 (5) | C5B—C6B | 1.361 (5) |
C5A—C7A | 1.474 (6) | C5B—C7B | 1.480 (5) |
C6A—N1A | 1.345 (5) | C6B—N1B | 1.339 (5) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—F10C | 1.310 (10) | C7B—F10B | 1.320 (9) |
C7A—F9C | 1.322 (10) | C7B—F8D | 1.310 (11) |
C7A—F9A | 1.325 (10) | C7B—F8B | 1.330 (9) |
C7A—F10A | 1.332 (9) | C7B—F9D | 1.324 (11) |
C7A—F8A | 1.342 (10) | C7B—F9B | 1.336 (7) |
C7A—F8C | 1.350 (8) | C7B—F10D | 1.358 (10) |
C12A—N11A | 1.390 (5) | C12B—N11B | 1.390 (5) |
C12A—C17A | 1.400 (5) | C12B—C17B | 1.394 (5) |
C12A—C13A | 1.415 (5) | C12B—C13B | 1.426 (5) |
C13A—C14A | 1.394 (5) | C13B—C14B | 1.387 (5) |
C13A—C18A | 1.470 (5) | C13B—C18B | 1.470 (5) |
C14A—C15A | 1.360 (6) | C14B—C15B | 1.367 (5) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—F15A | 1.375 (5) | C15B—F15B | 1.352 (4) |
C15A—C16A | 1.376 (6) | C15B—C16B | 1.375 (6) |
C16A—C17A | 1.373 (6) | C16B—C17B | 1.383 (5) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—N22A | 1.269 (5) | C18B—N22B | 1.275 (5) |
C18A—O19A | 1.365 (5) | C18B—O19B | 1.354 (5) |
C20A—O19A | 1.436 (5) | C20B—O19B | 1.451 (5) |
C20A—C21A | 1.546 (7) | C20B—C21B | 1.533 (6) |
C20A—H20A | 0.9700 | C20B—H20C | 0.9700 |
C20A—H20B | 0.9700 | C20B—H20D | 0.9700 |
C21A—N22A | 1.469 (5) | C21B—N22B | 1.472 (5) |
C21A—C23A | 1.526 (5) | C21B—C23B | 1.521 (6) |
C21A—H21A | 0.9800 | C21B—H21B | 0.9800 |
C23A—C24A | 1.519 (7) | C23B—C25B | 1.515 (6) |
C23A—C25A | 1.530 (6) | C23B—C24B | 1.514 (7) |
C23A—H23A | 0.9800 | C23B—H23B | 0.9800 |
C24A—H24A | 0.9600 | C24B—H24D | 0.9600 |
C24A—H24B | 0.9600 | C24B—H24E | 0.9600 |
C24A—H24C | 0.9600 | C24B—H24F | 0.9600 |
C25A—H25A | 0.9600 | C25B—H25D | 0.9600 |
C25A—H25B | 0.9600 | C25B—H25E | 0.9600 |
C25A—H25C | 0.9600 | C25B—H25F | 0.9600 |
N11A—H11A | 1.00 (6) | N11B—H11B | 0.94 (6) |
| | | |
N1A—C2A—N11A | 121.9 (3) | N1B—C2B—N11B | 121.6 (3) |
N1A—C2A—C3A | 121.9 (4) | N1B—C2B—C3B | 122.5 (3) |
N11A—C2A—C3A | 116.2 (3) | N11B—C2B—C3B | 115.8 (3) |
C4A—C3A—C2A | 119.5 (4) | C4B—C3B—C2B | 119.0 (3) |
C4A—C3A—H3A | 120.2 | C4B—C3B—H3B | 120.5 |
C2A—C3A—H3A | 120.2 | C2B—C3B—H3B | 120.5 |
C3A—C4A—C5A | 118.8 (4) | C3B—C4B—C5B | 118.7 (3) |
C3A—C4A—H4A | 120.6 | C3B—C4B—H4B | 120.6 |
C5A—C4A—H4A | 120.6 | C5B—C4B—H4B | 120.6 |
C6A—C5A—C4A | 117.6 (4) | C6B—C5B—C4B | 117.8 (3) |
C6A—C5A—C7A | 122.2 (4) | C6B—C5B—C7B | 122.4 (3) |
C4A—C5A—C7A | 120.2 (3) | C4B—C5B—C7B | 119.8 (3) |
N1A—C6A—C5A | 124.6 (4) | N1B—C6B—C5B | 125.1 (4) |
N1A—C6A—H6A | 117.7 | N1B—C6B—H6B | 117.5 |
C5A—C6A—H6A | 117.7 | C5B—C6B—H6B | 117.5 |
F10C—C7A—F9C | 107.9 (9) | F10B—C7B—F8B | 107.5 (8) |
F9A—C7A—F10A | 105.6 (9) | F8D—C7B—F9D | 107.5 (11) |
F9A—C7A—F8A | 105.4 (10) | F10B—C7B—F9B | 105.6 (6) |
F10A—C7A—F8A | 105.8 (9) | F8B—C7B—F9B | 102.9 (8) |
F10C—C7A—F8C | 104.9 (9) | F8D—C7B—F10D | 106.5 (10) |
F9C—C7A—F8C | 104.7 (8) | F9D—C7B—F10D | 105.3 (10) |
F10C—C7A—C5A | 114.9 (10) | F10B—C7B—C5B | 115.2 (7) |
F9C—C7A—C5A | 113.9 (10) | F8D—C7B—C5B | 111.6 (13) |
F9A—C7A—C5A | 111.2 (11) | F8B—C7B—C5B | 114.2 (8) |
F10A—C7A—C5A | 111.2 (10) | F9D—C7B—C5B | 116.2 (11) |
F8A—C7A—C5A | 116.8 (9) | F9B—C7B—C5B | 110.5 (5) |
F8C—C7A—C5A | 109.5 (7) | F10D—C7B—C5B | 109.2 (9) |
N11A—C12A—C17A | 124.2 (3) | N11B—C12B—C17B | 124.4 (3) |
N11A—C12A—C13A | 117.6 (3) | N11B—C12B—C13B | 117.6 (3) |
C17A—C12A—C13A | 118.3 (3) | C17B—C12B—C13B | 118.0 (3) |
C14A—C13A—C12A | 119.6 (3) | C14B—C13B—C12B | 119.8 (3) |
C14A—C13A—C18A | 118.3 (3) | C14B—C13B—C18B | 118.7 (3) |
C12A—C13A—C18A | 122.0 (3) | C12B—C13B—C18B | 121.5 (3) |
C15A—C14A—C13A | 119.4 (4) | C15B—C14B—C13B | 119.8 (3) |
C15A—C14A—H14A | 120.3 | C15B—C14B—H14B | 120.1 |
C13A—C14A—H14A | 120.3 | C13B—C14B—H14B | 120.1 |
C14A—C15A—F15A | 119.0 (4) | F15B—C15B—C14B | 119.6 (3) |
C14A—C15A—C16A | 122.8 (4) | F15B—C15B—C16B | 118.4 (3) |
F15A—C15A—C16A | 118.1 (4) | C14B—C15B—C16B | 122.0 (3) |
C17A—C16A—C15A | 118.4 (4) | C15B—C16B—C17B | 118.9 (3) |
C17A—C16A—H16A | 120.8 | C15B—C16B—H16B | 120.5 |
C15A—C16A—H16A | 120.8 | C17B—C16B—H16B | 120.5 |
C16A—C17A—C12A | 121.6 (4) | C16B—C17B—C12B | 121.4 (3) |
C16A—C17A—H17A | 119.2 | C16B—C17B—H17B | 119.3 |
C12A—C17A—H17A | 119.2 | C12B—C17B—H17B | 119.3 |
N22A—C18A—O19A | 117.6 (3) | N22B—C18B—O19B | 117.8 (3) |
N22A—C18A—C13A | 126.8 (3) | N22B—C18B—C13B | 126.5 (3) |
O19A—C18A—C13A | 115.6 (3) | O19B—C18B—C13B | 115.7 (3) |
O19A—C20A—C21A | 104.6 (3) | O19B—C20B—C21B | 104.2 (3) |
O19A—C20A—H20A | 110.8 | O19B—C20B—H20C | 110.9 |
C21A—C20A—H20A | 110.8 | C21B—C20B—H20C | 110.9 |
O19A—C20A—H20B | 110.8 | O19B—C20B—H20D | 110.9 |
C21A—C20A—H20B | 110.8 | C21B—C20B—H20D | 110.9 |
H20A—C20A—H20B | 108.9 | H20C—C20B—H20D | 108.9 |
N22A—C21A—C23A | 112.4 (3) | N22B—C21B—C23B | 113.3 (3) |
N22A—C21A—C20A | 103.3 (3) | N22B—C21B—C20B | 103.4 (3) |
C23A—C21A—C20A | 114.7 (3) | C23B—C21B—C20B | 114.9 (3) |
N22A—C21A—H21A | 108.8 | N22B—C21B—H21B | 108.3 |
C23A—C21A—H21A | 108.8 | C23B—C21B—H21B | 108.3 |
C20A—C21A—H21A | 108.8 | C20B—C21B—H21B | 108.3 |
C24A—C23A—C21A | 111.6 (4) | C25B—C23B—C24B | 111.0 (4) |
C24A—C23A—C25A | 110.8 (4) | C25B—C23B—C21B | 109.7 (4) |
C21A—C23A—C25A | 110.0 (3) | C24B—C23B—C21B | 111.6 (3) |
C24A—C23A—H23A | 108.1 | C25B—C23B—H23B | 108.1 |
C21A—C23A—H23A | 108.1 | C24B—C23B—H23B | 108.1 |
C25A—C23A—H23A | 108.1 | C21B—C23B—H23B | 108.1 |
C23A—C24A—H24A | 109.5 | C23B—C24B—H24D | 109.5 |
C23A—C24A—H24B | 109.5 | C23B—C24B—H24E | 109.5 |
H24A—C24A—H24B | 109.5 | H24D—C24B—H24E | 109.5 |
C23A—C24A—H24C | 109.5 | C23B—C24B—H24F | 109.5 |
H24A—C24A—H24C | 109.5 | H24D—C24B—H24F | 109.5 |
H24B—C24A—H24C | 109.5 | H24E—C24B—H24F | 109.5 |
C23A—C25A—H25A | 109.5 | C23B—C25B—H25D | 109.5 |
C23A—C25A—H25B | 109.5 | C23B—C25B—H25E | 109.5 |
H25A—C25A—H25B | 109.5 | H25D—C25B—H25E | 109.5 |
C23A—C25A—H25C | 109.5 | C23B—C25B—H25F | 109.5 |
H25A—C25A—H25C | 109.5 | H25D—C25B—H25F | 109.5 |
H25B—C25A—H25C | 109.5 | H25E—C25B—H25F | 109.5 |
C2A—N1A—C6A | 117.4 (3) | C2B—N1B—C6B | 116.7 (3) |
C2A—N11A—C12A | 131.6 (3) | C2B—N11B—C12B | 131.5 (3) |
C2A—N11A—H11A | 113 (3) | C2B—N11B—H11B | 121 (3) |
C12A—N11A—H11A | 115 (3) | C12B—N11B—H11B | 108 (3) |
C18A—N22A—C21A | 107.9 (3) | C18B—N22B—C21B | 107.3 (3) |
C18A—O19A—C20A | 106.0 (3) | C18B—O19B—C20B | 105.6 (3) |
| | | |
N1A—C2A—C3A—C4A | 4.2 (6) | N1B—C2B—C3B—C4B | −3.9 (6) |
N11A—C2A—C3A—C4A | −176.8 (4) | N11B—C2B—C3B—C4B | 176.3 (4) |
C2A—C3A—C4A—C5A | −0.3 (7) | C2B—C3B—C4B—C5B | 0.5 (6) |
C3A—C4A—C5A—C6A | −3.3 (6) | C3B—C4B—C5B—C6B | 2.8 (6) |
C3A—C4A—C5A—C7A | 176.1 (4) | C3B—C4B—C5B—C7B | −176.8 (4) |
C4A—C5A—C6A—N1A | 3.5 (6) | C4B—C5B—C6B—N1B | −3.3 (6) |
C7A—C5A—C6A—N1A | −175.9 (4) | C7B—C5B—C6B—N1B | 176.4 (4) |
C6A—C5A—C7A—F10C | −15.8 (17) | C6B—C5B—C7B—F10B | 119.3 (10) |
C4A—C5A—C7A—F10C | 164.9 (16) | C4B—C5B—C7B—F10B | −61.1 (11) |
C6A—C5A—C7A—F9C | 109.5 (13) | C6B—C5B—C7B—F8D | 21.8 (14) |
C4A—C5A—C7A—F9C | −69.8 (13) | C4B—C5B—C7B—F8D | −158.6 (14) |
C6A—C5A—C7A—F9A | 128.5 (12) | C6B—C5B—C7B—F8B | −5.7 (13) |
C4A—C5A—C7A—F9A | −50.8 (13) | C4B—C5B—C7B—F8B | 173.9 (12) |
C6A—C5A—C7A—F10A | 11.1 (14) | C6B—C5B—C7B—F9D | −101.9 (16) |
C4A—C5A—C7A—F10A | −168.2 (13) | C4B—C5B—C7B—F9D | 77.7 (16) |
C6A—C5A—C7A—F8A | −110.4 (15) | C6B—C5B—C7B—F9B | −121.2 (8) |
C4A—C5A—C7A—F8A | 70.2 (16) | C4B—C5B—C7B—F9B | 58.5 (8) |
C6A—C5A—C7A—F8C | −133.6 (11) | C6B—C5B—C7B—F10D | 139.2 (12) |
C4A—C5A—C7A—F8C | 47.1 (11) | C4B—C5B—C7B—F10D | −41.1 (13) |
N11A—C12A—C13A—C14A | −179.4 (3) | N11B—C12B—C13B—C14B | 178.1 (3) |
C17A—C12A—C13A—C14A | 1.8 (5) | C17B—C12B—C13B—C14B | −2.2 (5) |
N11A—C12A—C13A—C18A | 3.3 (5) | N11B—C12B—C13B—C18B | −5.3 (5) |
C17A—C12A—C13A—C18A | −175.5 (3) | C17B—C12B—C13B—C18B | 174.4 (3) |
C12A—C13A—C14A—C15A | −0.3 (5) | C12B—C13B—C14B—C15B | 0.8 (5) |
C18A—C13A—C14A—C15A | 177.1 (4) | C18B—C13B—C14B—C15B | −175.9 (4) |
C13A—C14A—C15A—F15A | 179.3 (3) | C13B—C14B—C15B—F15B | −179.9 (4) |
C13A—C14A—C15A—C16A | −1.4 (6) | C13B—C14B—C15B—C16B | 1.5 (6) |
C14A—C15A—C16A—C17A | 1.5 (7) | F15B—C15B—C16B—C17B | 179.0 (4) |
F15A—C15A—C16A—C17A | −179.2 (4) | C14B—C15B—C16B—C17B | −2.3 (7) |
C15A—C16A—C17A—C12A | 0.1 (6) | C15B—C16B—C17B—C12B | 0.8 (6) |
N11A—C12A—C17A—C16A | 179.5 (4) | N11B—C12B—C17B—C16B | −179.0 (4) |
C13A—C12A—C17A—C16A | −1.7 (6) | C13B—C12B—C17B—C16B | 1.4 (6) |
C14A—C13A—C18A—N22A | −179.1 (4) | C14B—C13B—C18B—N22B | 175.4 (4) |
C12A—C13A—C18A—N22A | −1.8 (6) | C12B—C13B—C18B—N22B | −1.3 (6) |
C14A—C13A—C18A—O19A | 0.7 (5) | C14B—C13B—C18B—O19B | −1.7 (5) |
C12A—C13A—C18A—O19A | 178.0 (3) | C12B—C13B—C18B—O19B | −178.4 (3) |
O19A—C20A—C21A—N22A | 7.1 (4) | O19B—C20B—C21B—N22B | 13.1 (4) |
O19A—C20A—C21A—C23A | 129.7 (4) | O19B—C20B—C21B—C23B | 137.1 (4) |
N22A—C21A—C23A—C24A | −57.9 (5) | N22B—C21B—C23B—C25B | −179.2 (3) |
C20A—C21A—C23A—C24A | −175.5 (4) | C20B—C21B—C23B—C25B | 62.3 (5) |
N22A—C21A—C23A—C25A | 178.7 (4) | N22B—C21B—C23B—C24B | −55.7 (5) |
C20A—C21A—C23A—C25A | 61.1 (5) | C20B—C21B—C23B—C24B | −174.2 (4) |
N11A—C2A—N1A—C6A | 176.9 (4) | N11B—C2B—N1B—C6B | −176.6 (4) |
C3A—C2A—N1A—C6A | −4.1 (6) | C3B—C2B—N1B—C6B | 3.6 (6) |
C5A—C6A—N1A—C2A | 0.2 (6) | C5B—C6B—N1B—C2B | 0.1 (6) |
N1A—C2A—N11A—C12A | −5.4 (6) | N1B—C2B—N11B—C12B | 0.4 (6) |
C3A—C2A—N11A—C12A | 175.6 (4) | C3B—C2B—N11B—C12B | −179.8 (4) |
C17A—C12A—N11A—C2A | −3.5 (7) | C17B—C12B—N11B—C2B | 0.6 (6) |
C13A—C12A—N11A—C2A | 177.8 (4) | C13B—C12B—N11B—C2B | −179.7 (4) |
O19A—C18A—N22A—C21A | −0.3 (4) | O19B—C18B—N22B—C21B | 3.3 (5) |
C13A—C18A—N22A—C21A | 179.5 (3) | C13B—C18B—N22B—C21B | −173.8 (3) |
C23A—C21A—N22A—C18A | −128.5 (4) | C23B—C21B—N22B—C18B | −135.2 (4) |
C20A—C21A—N22A—C18A | −4.3 (4) | C20B—C21B—N22B—C18B | −10.2 (4) |
N22A—C18A—O19A—C20A | 5.2 (5) | N22B—C18B—O19B—C20B | 5.7 (5) |
C13A—C18A—O19A—C20A | −174.6 (3) | C13B—C18B—O19B—C20B | −176.9 (3) |
C21A—C20A—O19A—C18A | −7.3 (4) | C21B—C20B—O19B—C18B | −11.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11A—H11A···N22A | 1.00 (6) | 1.83 (7) | 2.667 (5) | 139 (6) |
N11B—H11B···N22B | 0.95 (6) | 1.78 (7) | 2.655 (4) | 153 (5) |
C14A—H14A···O19A | 0.93 | 2.37 | 2.722 (4) | 102 |
C14B—H14B···O19B | 0.93 | 2.38 | 2.721 (4) | 102 |
C17A—H17A···N1A | 0.93 | 2.33 | 2.948 (5) | 124 |
C17B—H17B···N1B | 0.93 | 2.31 | 2.937 (5) | 124 |
C24B—H24F···N22B | 0.96 | 2.60 | 2.957 (6) | 102 |
2-({2-[(3a
R,8a
S)-8,8a-Dihydro-3a
H-indeno[1,2-
d]oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine (5c)
top
Crystal data top
C22H16F3N3O | F(000) = 408 |
Mr = 395.38 | Dx = 1.395 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 4.9330 (5) Å | Cell parameters from 2391 reflections |
b = 10.9919 (6) Å | θ = 4.0–75.4° |
c = 17.4202 (14) Å | µ = 0.92 mm−1 |
β = 94.718 (8)° | T = 297 K |
V = 941.38 (13) Å3 | Needle, colourless |
Z = 2 | 0.30 × 0.10 × 0.10 mm |
Data collection top
Agilent SuperNova Single Source diffractometer with an Atlas detector | 3332 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 3035 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.025 |
Detector resolution: 5.2763 pixels mm-1 | θmax = 75.9°, θmin = 4.8° |
ω scans | h = −6→5 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2015) | k = −13→13 |
Tmin = 0.568, Tmax = 1.000 | l = −20→21 |
5822 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0683P)2 + 0.3366P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3332 reflections | Δρmax = 0.24 e Å−3 |
265 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Absolute structure: Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.15 (16) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C2 | −0.2083 (9) | 0.5515 (4) | 0.3128 (3) | 0.0549 (10) | |
C3 | −0.1639 (12) | 0.6017 (4) | 0.3870 (3) | 0.0682 (12) | |
H3 | −0.0466 | 0.6673 | 0.3959 | 0.102* | |
C4 | −0.2942 (13) | 0.5533 (5) | 0.4458 (3) | 0.0727 (14) | |
H4 | −0.2675 | 0.5853 | 0.4952 | 0.109* | |
C5 | −0.4691 (10) | 0.4543 (5) | 0.4304 (3) | 0.0625 (11) | |
C6 | −0.4988 (12) | 0.4125 (5) | 0.3570 (3) | 0.0735 (14) | |
H6 | −0.6166 | 0.3474 | 0.3468 | 0.110* | |
C7 | −0.6010 (12) | 0.3954 (6) | 0.4939 (3) | 0.0774 (15) | |
C12 | −0.0573 (9) | 0.5712 (4) | 0.1789 (3) | 0.0529 (9) | |
C13 | 0.1285 (8) | 0.6356 (4) | 0.1359 (3) | 0.0529 (9) | |
C14 | 0.1465 (11) | 0.6065 (5) | 0.0589 (3) | 0.0697 (13) | |
H14 | 0.2650 | 0.6503 | 0.0306 | 0.105* | |
C15 | −0.0074 (13) | 0.5139 (6) | 0.0233 (3) | 0.0797 (15) | |
H15 | 0.0111 | 0.4933 | −0.0278 | 0.119* | |
C16 | −0.1889 (12) | 0.4534 (5) | 0.0657 (3) | 0.0729 (13) | |
H16 | −0.2973 | 0.3927 | 0.0421 | 0.109* | |
C17 | −0.2143 (10) | 0.4797 (4) | 0.1410 (3) | 0.0628 (11) | |
H17 | −0.3379 | 0.4362 | 0.1679 | 0.094* | |
C18 | 0.2949 (8) | 0.7362 (4) | 0.1707 (3) | 0.0523 (9) | |
C20 | 0.6059 (8) | 0.8866 (5) | 0.1685 (3) | 0.0643 (12) | |
H20 | 0.7995 | 0.8654 | 0.1715 | 0.097* | |
C21 | 0.4891 (9) | 0.8761 (4) | 0.2475 (3) | 0.0585 (10) | |
H21 | 0.6331 | 0.8682 | 0.2894 | 0.088* | |
C23 | 0.5557 (10) | 1.0171 (5) | 0.1397 (3) | 0.0672 (12) | |
H23A | 0.7239 | 1.0632 | 0.1427 | 0.101* | |
H23B | 0.4762 | 1.0176 | 0.0869 | 0.101* | |
C24 | 0.3623 (9) | 1.0684 (4) | 0.1929 (3) | 0.0604 (11) | |
C25 | 0.2253 (12) | 1.1798 (5) | 0.1885 (4) | 0.0750 (15) | |
H25 | 0.2490 | 1.2336 | 0.1484 | 0.113* | |
C26 | 0.0545 (13) | 1.2083 (6) | 0.2445 (4) | 0.0849 (17) | |
H26 | −0.0397 | 1.2817 | 0.2414 | 0.127* | |
C27 | 0.0198 (12) | 1.1307 (6) | 0.3051 (4) | 0.0786 (15) | |
H27 | −0.0949 | 1.1524 | 0.3426 | 0.118* | |
C28 | 0.1554 (9) | 1.0209 (5) | 0.3100 (3) | 0.0645 (12) | |
H28 | 0.1311 | 0.9675 | 0.3502 | 0.097* | |
C29 | 0.3274 (8) | 0.9914 (4) | 0.2544 (3) | 0.0543 (10) | |
N1 | −0.3732 (9) | 0.4570 (4) | 0.2980 (2) | 0.0703 (11) | |
N11 | −0.0664 (9) | 0.6004 (4) | 0.2560 (2) | 0.0598 (9) | |
H11 | 0.048 (15) | 0.644 (7) | 0.273 (4) | 0.090* | |
N22 | 0.3135 (7) | 0.7672 (3) | 0.2408 (2) | 0.0553 (8) | |
O19 | 0.4408 (7) | 0.8000 (3) | 0.1213 (2) | 0.0670 (9) | |
F8 | −0.6963 (10) | 0.4752 (5) | 0.5435 (2) | 0.1165 (15) | |
F9 | −0.8115 (8) | 0.3259 (4) | 0.4696 (2) | 0.0995 (11) | |
F10 | −0.4317 (9) | 0.3245 (4) | 0.5378 (2) | 0.1147 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.061 (2) | 0.043 (2) | 0.062 (2) | 0.0034 (18) | 0.0093 (18) | −0.0013 (18) |
C3 | 0.093 (3) | 0.049 (3) | 0.063 (3) | −0.012 (2) | 0.010 (2) | −0.007 (2) |
C4 | 0.104 (4) | 0.054 (3) | 0.061 (3) | −0.009 (3) | 0.014 (3) | −0.006 (2) |
C5 | 0.066 (3) | 0.053 (2) | 0.069 (3) | 0.001 (2) | 0.010 (2) | 0.004 (2) |
C6 | 0.081 (3) | 0.065 (3) | 0.076 (3) | −0.021 (3) | 0.017 (3) | −0.008 (2) |
C7 | 0.077 (3) | 0.081 (4) | 0.075 (3) | −0.009 (3) | 0.013 (3) | 0.006 (3) |
C12 | 0.054 (2) | 0.046 (2) | 0.059 (2) | 0.0061 (17) | 0.0070 (17) | −0.0004 (18) |
C13 | 0.045 (2) | 0.050 (2) | 0.064 (2) | 0.0096 (16) | 0.0063 (17) | −0.0039 (19) |
C14 | 0.067 (3) | 0.078 (3) | 0.066 (3) | −0.001 (3) | 0.014 (2) | −0.004 (3) |
C15 | 0.087 (4) | 0.094 (4) | 0.058 (3) | −0.001 (3) | 0.009 (2) | −0.020 (3) |
C16 | 0.085 (3) | 0.065 (3) | 0.068 (3) | −0.004 (3) | 0.000 (2) | −0.011 (2) |
C17 | 0.070 (3) | 0.050 (3) | 0.067 (3) | −0.001 (2) | 0.001 (2) | −0.002 (2) |
C18 | 0.0372 (18) | 0.056 (2) | 0.065 (2) | 0.0045 (16) | 0.0084 (15) | 0.0004 (19) |
C20 | 0.0352 (19) | 0.075 (3) | 0.084 (3) | −0.003 (2) | 0.0095 (18) | −0.007 (3) |
C21 | 0.055 (2) | 0.057 (3) | 0.062 (2) | −0.001 (2) | −0.0020 (18) | 0.004 (2) |
C23 | 0.057 (2) | 0.075 (3) | 0.071 (3) | −0.018 (2) | 0.012 (2) | 0.002 (2) |
C24 | 0.054 (2) | 0.059 (3) | 0.069 (3) | −0.012 (2) | 0.0012 (19) | 0.004 (2) |
C25 | 0.082 (3) | 0.051 (3) | 0.090 (4) | −0.008 (2) | −0.007 (3) | 0.005 (3) |
C26 | 0.088 (4) | 0.060 (3) | 0.105 (5) | 0.007 (3) | −0.008 (3) | −0.018 (3) |
C27 | 0.073 (3) | 0.075 (4) | 0.089 (4) | 0.002 (3) | 0.007 (3) | −0.023 (3) |
C28 | 0.056 (2) | 0.068 (3) | 0.070 (3) | −0.007 (2) | 0.008 (2) | −0.008 (2) |
C29 | 0.048 (2) | 0.054 (2) | 0.060 (2) | −0.0076 (18) | 0.0004 (16) | −0.0014 (19) |
N1 | 0.081 (3) | 0.061 (2) | 0.070 (3) | −0.017 (2) | 0.014 (2) | −0.014 (2) |
N11 | 0.066 (2) | 0.051 (2) | 0.063 (2) | −0.0055 (18) | 0.0101 (17) | −0.0051 (17) |
N22 | 0.0508 (18) | 0.054 (2) | 0.061 (2) | 0.0019 (15) | 0.0024 (14) | 0.0038 (16) |
O19 | 0.0599 (17) | 0.070 (2) | 0.073 (2) | −0.0108 (15) | 0.0205 (14) | −0.0098 (17) |
F8 | 0.140 (3) | 0.123 (3) | 0.094 (3) | −0.016 (3) | 0.057 (2) | −0.013 (2) |
F9 | 0.099 (2) | 0.099 (3) | 0.102 (2) | −0.031 (2) | 0.0194 (19) | 0.009 (2) |
F10 | 0.115 (3) | 0.115 (3) | 0.112 (3) | −0.009 (3) | 0.005 (2) | 0.052 (3) |
Geometric parameters (Å, º) top
C2—N1 | 1.330 (6) | C17—H17 | 0.9300 |
C2—N11 | 1.368 (6) | C18—N22 | 1.262 (6) |
C2—C3 | 1.407 (6) | C18—O19 | 1.361 (5) |
C3—C4 | 1.361 (7) | C20—O19 | 1.462 (6) |
C3—H3 | 0.9300 | C20—C23 | 1.533 (8) |
C4—C5 | 1.401 (7) | C20—C21 | 1.539 (7) |
C4—H4 | 0.9300 | C20—H20 | 0.9800 |
C5—C6 | 1.357 (7) | C21—N22 | 1.477 (6) |
C5—C7 | 1.478 (7) | C21—C29 | 1.508 (7) |
C6—N1 | 1.335 (7) | C21—H21 | 0.9800 |
C6—H6 | 0.9300 | C23—C24 | 1.494 (7) |
C7—F9 | 1.330 (7) | C23—H23A | 0.9700 |
C7—F10 | 1.335 (7) | C23—H23B | 0.9700 |
C7—F8 | 1.343 (7) | C24—C29 | 1.387 (6) |
C12—N11 | 1.386 (6) | C24—C25 | 1.397 (7) |
C12—C17 | 1.401 (6) | C25—C26 | 1.378 (10) |
C12—C13 | 1.420 (6) | C25—H25 | 0.9300 |
C13—C14 | 1.388 (7) | C26—C27 | 1.379 (9) |
C13—C18 | 1.478 (6) | C26—H26 | 0.9300 |
C14—C15 | 1.386 (8) | C27—C28 | 1.379 (8) |
C14—H14 | 0.9300 | C27—H27 | 0.9300 |
C15—C16 | 1.379 (8) | C28—C29 | 1.377 (7) |
C15—H15 | 0.9300 | C28—H28 | 0.9300 |
C16—C17 | 1.359 (7) | N11—H11 | 0.78 (7) |
C16—H16 | 0.9300 | | |
| | | |
N1—C2—N11 | 120.6 (4) | O19—C20—C23 | 111.0 (4) |
N1—C2—C3 | 122.0 (4) | O19—C20—C21 | 102.8 (4) |
N11—C2—C3 | 117.4 (4) | C23—C20—C21 | 107.5 (4) |
C4—C3—C2 | 119.4 (5) | O19—C20—H20 | 111.7 |
C4—C3—H3 | 120.3 | C23—C20—H20 | 111.7 |
C2—C3—H3 | 120.3 | C21—C20—H20 | 111.7 |
C3—C4—C5 | 118.8 (5) | N22—C21—C29 | 112.1 (3) |
C3—C4—H4 | 120.6 | N22—C21—C20 | 104.5 (4) |
C5—C4—H4 | 120.6 | C29—C21—C20 | 104.3 (4) |
C6—C5—C4 | 117.4 (5) | N22—C21—H21 | 111.8 |
C6—C5—C7 | 122.5 (5) | C29—C21—H21 | 111.8 |
C4—C5—C7 | 120.0 (5) | C20—C21—H21 | 111.8 |
N1—C6—C5 | 125.5 (5) | C24—C23—C20 | 104.2 (4) |
N1—C6—H6 | 117.3 | C24—C23—H23A | 110.9 |
C5—C6—H6 | 117.3 | C20—C23—H23A | 110.9 |
F9—C7—F10 | 106.4 (5) | C24—C23—H23B | 110.9 |
F9—C7—F8 | 106.0 (5) | C20—C23—H23B | 110.9 |
F10—C7—F8 | 104.4 (5) | H23A—C23—H23B | 108.9 |
F9—C7—C5 | 113.2 (5) | C29—C24—C25 | 119.2 (5) |
F10—C7—C5 | 113.0 (5) | C29—C24—C23 | 112.0 (4) |
F8—C7—C5 | 113.2 (5) | C25—C24—C23 | 128.8 (5) |
N11—C12—C17 | 124.2 (4) | C26—C25—C24 | 118.8 (6) |
N11—C12—C13 | 118.0 (4) | C26—C25—H25 | 120.6 |
C17—C12—C13 | 117.7 (4) | C24—C25—H25 | 120.6 |
C14—C13—C12 | 119.4 (4) | C27—C26—C25 | 121.6 (6) |
C14—C13—C18 | 119.4 (4) | C27—C26—H26 | 119.2 |
C12—C13—C18 | 121.2 (4) | C25—C26—H26 | 119.2 |
C15—C14—C13 | 121.7 (5) | C28—C27—C26 | 119.9 (6) |
C15—C14—H14 | 119.1 | C28—C27—H27 | 120.1 |
C13—C14—H14 | 119.1 | C26—C27—H27 | 120.1 |
C16—C15—C14 | 118.0 (5) | C27—C28—C29 | 119.1 (5) |
C16—C15—H15 | 121.0 | C27—C28—H28 | 120.4 |
C14—C15—H15 | 121.0 | C29—C28—H28 | 120.4 |
C17—C16—C15 | 122.1 (5) | C28—C29—C24 | 121.4 (5) |
C17—C16—H16 | 119.0 | C28—C29—C21 | 127.9 (4) |
C15—C16—H16 | 119.0 | C24—C29—C21 | 110.6 (4) |
C16—C17—C12 | 121.0 (5) | C2—N1—C6 | 116.9 (4) |
C16—C17—H17 | 119.5 | C2—N11—C12 | 131.9 (4) |
C12—C17—H17 | 119.5 | C2—N11—H11 | 111 (5) |
N22—C18—O19 | 118.2 (4) | C12—N11—H11 | 116 (5) |
N22—C18—C13 | 126.3 (4) | C18—N22—C21 | 106.9 (4) |
O19—C18—C13 | 115.5 (4) | C18—O19—C20 | 106.1 (4) |
| | | |
N1—C2—C3—C4 | −0.5 (8) | C21—C20—C23—C24 | −12.0 (5) |
N11—C2—C3—C4 | −177.9 (5) | C20—C23—C24—C29 | 8.8 (5) |
C2—C3—C4—C5 | 0.1 (8) | C20—C23—C24—C25 | −172.4 (5) |
C3—C4—C5—C6 | −0.2 (8) | C29—C24—C25—C26 | −1.5 (7) |
C3—C4—C5—C7 | 176.5 (5) | C23—C24—C25—C26 | 179.9 (5) |
C4—C5—C6—N1 | 0.7 (9) | C24—C25—C26—C27 | 1.1 (9) |
C7—C5—C6—N1 | −175.9 (6) | C25—C26—C27—C28 | −0.8 (9) |
C6—C5—C7—F9 | −20.1 (8) | C26—C27—C28—C29 | 1.0 (8) |
C4—C5—C7—F9 | 163.4 (5) | C27—C28—C29—C24 | −1.4 (7) |
C6—C5—C7—F10 | 100.9 (7) | C27—C28—C29—C21 | −178.4 (4) |
C4—C5—C7—F10 | −75.6 (7) | C25—C24—C29—C28 | 1.7 (6) |
C6—C5—C7—F8 | −140.7 (6) | C23—C24—C29—C28 | −179.4 (4) |
C4—C5—C7—F8 | 42.8 (7) | C25—C24—C29—C21 | 179.2 (4) |
N11—C12—C13—C14 | 178.6 (4) | C23—C24—C29—C21 | −2.0 (5) |
C17—C12—C13—C14 | 0.4 (6) | N22—C21—C29—C28 | 59.0 (6) |
N11—C12—C13—C18 | −3.8 (6) | C20—C21—C29—C28 | 171.5 (4) |
C17—C12—C13—C18 | 177.9 (4) | N22—C21—C29—C24 | −118.2 (4) |
C12—C13—C14—C15 | −1.6 (7) | C20—C21—C29—C24 | −5.7 (5) |
C18—C13—C14—C15 | −179.2 (5) | N11—C2—N1—C6 | 178.3 (5) |
C13—C14—C15—C16 | 2.4 (9) | C3—C2—N1—C6 | 0.9 (7) |
C14—C15—C16—C17 | −1.8 (9) | C5—C6—N1—C2 | −1.0 (9) |
C15—C16—C17—C12 | 0.6 (8) | N1—C2—N11—C12 | 0.7 (8) |
N11—C12—C17—C16 | −178.0 (5) | C3—C2—N11—C12 | 178.2 (5) |
C13—C12—C17—C16 | 0.1 (7) | C17—C12—N11—C2 | 2.4 (8) |
C14—C13—C18—N22 | −174.8 (5) | C13—C12—N11—C2 | −175.7 (4) |
C12—C13—C18—N22 | 7.6 (6) | O19—C18—N22—C21 | 3.5 (5) |
C14—C13—C18—O19 | 5.0 (6) | C13—C18—N22—C21 | −176.7 (4) |
C12—C13—C18—O19 | −172.5 (4) | C29—C21—N22—C18 | 102.9 (4) |
O19—C20—C21—N22 | 11.7 (4) | C20—C21—N22—C18 | −9.6 (4) |
C23—C20—C21—N22 | 128.9 (4) | N22—C18—O19—C20 | 4.7 (5) |
O19—C20—C21—C29 | −106.2 (4) | C13—C18—O19—C20 | −175.2 (3) |
C23—C20—C21—C29 | 11.0 (5) | C23—C20—O19—C18 | −124.6 (4) |
O19—C20—C23—C24 | 99.7 (4) | C21—C20—O19—C18 | −10.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···N22 | 0.92 (6) | 1.83 (6) | 2.661 (6) | 149 (6) |
C6—H6···F9 | 0.93 | 2.43 | 2.762 (7) | 101 |
C14—H14···O19 | 0.93 | 2.39 | 2.748 (6) | 102 |
C17—H17···N1 | 0.93 | 2.30 | 2.915 (7) | 123 |
The rotational barrier energy and N11···N22 distance topCompound | Dihedral angle C—N—C—N, φ (°) | Rotational barrier energy, E (kcal mol-1) | N11···N22, d (Å) |
5a | 0 | 0.00 | 2.705 |
| 180 | 2.98 | 2.731 |
| 90 | 8.42 | 2.705 |
| -90 | 8.33 | 2.708 |
5b | 0 | 0.00 | 2.716 |
| 180 | 2.61 | 2.727 |
| 90 | 8.58 | 2.711 |
| -90 | 8.68 | 2.713 |
5c | 0 | 0.00 | 2.708 |
| 180 | 2.43 | 2.719 |
| 90 | 8.26 | 2.706 |
| -90 | 8.40 | 2.708 |
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