Synthesis and structures of three new pyridine-containing oxazoline ligands of com­plexes for asymmetric catalysis

Three new chiral pyridine-containing oxazoline derivatives with fluorine and perfluoro­methyl groups, namely, 2-({2-[(4S)-4-phenyl-4,5-di­hydro-1,3-oxazol-2-yl]phen­yl}amino)-5-(tri­fluoro­methyl)­pyridine, C₂₁H₁₆F₃N₃O, 2-({5-fluoro-2-[(4S)-4-isopropyl-4,5-di­hydro-1,3-oxazol-2-yl]phen­yl}amino)-5-(tri­fluoro­methyl)­pyridine, C₁₈H₁₇F₄N₃O, and 2-({2-[(3aR,8aS)-8,8a-di­hydro-3aH-in­deno­[1,2-d]oxazol-2-yl]phen­yl}amino)-5-(tri­fluoro­methyl)­pyridine, C₂₂H₁₆F₃N₃O, 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.

Computing details

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-[(4S)-4-Phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine (5a)

Crystal data

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) Å^3	T = 296 K
Z = 3	Prism, colourless
F(000) = 594	0.10 × 0.05 × 0.05 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0749P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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-[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine (5b)

Crystal data

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) Å^3	Prism, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0964P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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-[(3aR,8aS)-8,8a-Dihydro-3aH-indeno[1,2-d]oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine (5c)

Crystal data

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) Å^3	Needle, colourless
Z = 2	0.30 × 0.10 × 0.10 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.3366P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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