Evaluation of fluorine-mediated intermolecular interactions in tetrafluorinated tetra­hydro­iso­quinoline derivatives: synthesis and computational studies

Intermolecular interactions involving the aromatic C—F group in the absence of other strong hydrogen bond acceptors is the theme of this article. Weak interactions involving fluorine are known to generate various supramolecular synthons, thereby altering the crystal structures of small organic molecules. It is demonstrated that the weak interactions involving organic fluorine play a major role in directing crystal packing of highly flexible organic molecules like di­phenyl tetra­hydro­iso­quinolines reported herein. The intramolecular C—H...F hydrogen bonds are found to be significant in controlling the molecular conformation in specific cases wheras the intermolecular interactions involving the C—F groups result in a wide range of supramolecular synthons involving C—H...F and C—F...F—C interactions. The interactions are studied computationally to provide insight into their energies and the topology of the interactions is studied using Atoms in Molecules. C—H...F—C interactions are found to be quite stabilizing in nature with the stabilization energy of −13.9 kcal mol⁻¹.

Computing details

Data collection: CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011) for 6-1, 6-2, 6-3, 6-4, 6-5, 6-6, 6-7, 6-8, 6-9, 6-13, 6-16, 6-19, 6-21, 6-23, 6-25, 6-30, 6-31, 6-33, 6-34. Cell refinement: CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011) for 6-1, 6-2, 6-3, 6-4, 6-5, 6-6, 6-7, 6-8, 6-9, 6-13, 6-16, 6-19, 6-21, 6-23, 6-25, 6-30, 6-31, 6-33, 6-34; SAINT v8.34A (Bruker, 2013) for 6-37. Data reduction: CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011) for 6-1, 6-2, 6-3, 6-4, 6-5, 6-6, 6-7, 6-8, 6-9, 6-13, 6-16, 6-19, 6-21, 6-23, 6-25, 6-30, 6-31, 6-33, 6-34; SAINT v8.34A (Bruker, 2013) for 6-37. Program(s) used to solve structure: ShelXT (Sheldrick, 2015) for 6-1, 6-5, 6-6, 6-7, 6-8, 6-9, 6-13, 6-16, 6-19, 6-21, 6-23, 6-30, 6-31, 6-33, 6-34; SIR2004 (Burla et al., 2007) for 6-2; SHELXS (Sheldrick, 2008) for 6-3, 6-4; SHELXT (Sheldrick, 2014) for 6-25, 6-37. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

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Crystal data

C22H17F4NO	F(000) = 400
Mr = 387.36	Dx = 1.467 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2611 reflections
a = 8.210 (4) Å	θ = 3–27.5°
b = 6.330 (2) Å	µ = 0.12 mm^−1
c = 17.277 (9) Å	T = 100 K
β = 102.410 (19)°	Block, clear light colourless
V = 876.9 (7) Å^3	0.25 × 0.22 × 0.18 mm
Z = 2

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3361 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.043
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Blessing 1995	h = −10→10
Tmin = 0.798, Tmax = 1	k = −8→8
9368 measured reflections	l = −22→22
4001 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 0.0363P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.144	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.40 e Å^−3
4001 reflections	Δρmin = −0.27 e Å^−3
254 parameters	Absolute structure: Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: −0.2 (5)

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
C1	0.6381 (4)	0.5050 (5)	0.29011 (18)	0.0251 (7)
H1	0.616886	0.659849	0.281996	0.030*
C2	0.4796 (5)	0.1709 (6)	0.2782 (2)	0.0291 (7)
H2A	0.577736	0.095787	0.266968	0.035*
H2B	0.377717	0.100580	0.248253	0.035*
C3	0.4830 (5)	0.1615 (6)	0.3664 (2)	0.0315 (8)
H3A	0.373459	0.207674	0.375612	0.038*
H3B	0.501121	0.013589	0.384836	0.038*
C4	0.6728 (4)	0.2602 (6)	0.4950 (2)	0.0274 (7)
H4	0.626841	0.146160	0.518959	0.033*
C5	0.7940 (4)	0.3866 (5)	0.54080 (19)	0.0269 (7)
C6	0.8588 (4)	0.5567 (6)	0.5057 (2)	0.0281 (7)
H6	0.938945	0.647467	0.537012	0.034*
C7	0.8065 (4)	0.5931 (6)	0.42527 (19)	0.0278 (7)
H7	0.853343	0.706648	0.401430	0.033*
C8	0.6850 (4)	0.4646 (5)	0.37855 (19)	0.0258 (7)
C9	0.6171 (4)	0.2981 (5)	0.41393 (19)	0.0256 (7)
C10	0.8046 (5)	0.1700 (7)	0.6541 (2)	0.0349 (8)
H10A	0.832916	0.045521	0.625986	0.052*
H10B	0.683666	0.174992	0.649884	0.052*
H10C	0.861141	0.161613	0.710104	0.052*
C11	0.4299 (4)	0.4212 (5)	0.17016 (19)	0.0252 (7)
C12	0.3594 (4)	0.6155 (5)	0.1423 (2)	0.0283 (7)
C13	0.2976 (5)	0.6503 (6)	0.0625 (2)	0.0297 (7)
C14	0.3012 (4)	0.4965 (6)	0.0073 (2)	0.0295 (7)
H14	0.256943	0.521479	−0.047427	0.035*
C15	0.3714 (4)	0.3026 (6)	0.0336 (2)	0.0308 (8)
H15	0.375070	0.193162	−0.003615	0.037*
C16	0.4359 (4)	0.2670 (6)	0.1131 (2)	0.0282 (7)
H16	0.485572	0.134269	0.129399	0.034*
C17	0.7798 (4)	0.4443 (5)	0.24867 (19)	0.0266 (7)
C18	0.8109 (4)	0.5654 (6)	0.18685 (19)	0.0272 (7)
C19	0.9231 (4)	0.5066 (6)	0.14236 (19)	0.0312 (8)
C20	1.0120 (4)	0.3205 (6)	0.1581 (2)	0.0339 (8)
H20	1.088238	0.277832	0.126840	0.041*
C21	0.9865 (4)	0.1975 (6)	0.2213 (2)	0.0333 (8)
H21	1.046322	0.069021	0.233604	0.040*
C22	0.8739 (4)	0.2615 (6)	0.2666 (2)	0.0291 (7)
H22	0.861127	0.178257	0.310640	0.035*
N1	0.4819 (3)	0.3913 (4)	0.25347 (16)	0.0256 (6)
O1	0.8574 (3)	0.3576 (4)	0.61959 (13)	0.0306 (6)
F1	0.7279 (3)	0.7510 (3)	0.16848 (12)	0.0343 (5)
F2	0.9480 (3)	0.6344 (4)	0.08376 (13)	0.0399 (6)
F3	0.3469 (3)	0.7710 (4)	0.19399 (12)	0.0377 (5)
F4	0.2298 (3)	0.8411 (3)	0.04026 (13)	0.0393 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0273 (16)	0.0221 (16)	0.0251 (15)	−0.0027 (13)	0.0042 (12)	−0.0012 (13)
C2	0.0328 (17)	0.0248 (17)	0.0282 (17)	−0.0062 (14)	0.0034 (14)	−0.0017 (14)
C3	0.0336 (17)	0.0287 (18)	0.0310 (18)	−0.0091 (15)	0.0043 (14)	0.0034 (15)
C4	0.0278 (16)	0.0263 (16)	0.0276 (16)	−0.0003 (14)	0.0048 (13)	0.0001 (14)
C5	0.0284 (16)	0.0298 (18)	0.0234 (15)	0.0053 (14)	0.0075 (13)	−0.0009 (13)
C6	0.0274 (16)	0.0270 (17)	0.0284 (16)	−0.0045 (14)	0.0025 (13)	−0.0017 (14)
C7	0.0302 (17)	0.0275 (17)	0.0255 (16)	−0.0073 (14)	0.0054 (14)	−0.0022 (13)
C8	0.0290 (17)	0.0230 (16)	0.0251 (15)	−0.0020 (13)	0.0053 (13)	−0.0021 (13)
C9	0.0274 (16)	0.0253 (17)	0.0238 (15)	−0.0019 (14)	0.0050 (13)	−0.0022 (13)
C10	0.0345 (18)	0.038 (2)	0.0310 (18)	0.0029 (16)	0.0042 (15)	0.0074 (16)
C11	0.0218 (15)	0.0259 (17)	0.0269 (16)	−0.0051 (13)	0.0032 (12)	−0.0027 (13)
C12	0.0316 (18)	0.0235 (17)	0.0305 (17)	−0.0057 (13)	0.0082 (14)	−0.0044 (14)
C13	0.0297 (17)	0.0218 (16)	0.0377 (19)	−0.0038 (13)	0.0073 (15)	0.0029 (15)
C14	0.0264 (16)	0.0341 (19)	0.0265 (16)	−0.0033 (14)	0.0025 (13)	0.0010 (14)
C15	0.0263 (16)	0.0359 (19)	0.0306 (17)	−0.0006 (14)	0.0069 (14)	−0.0066 (15)
C16	0.0268 (16)	0.0258 (16)	0.0312 (16)	−0.0022 (14)	0.0042 (13)	−0.0042 (14)
C17	0.0244 (16)	0.0275 (18)	0.0258 (16)	−0.0053 (13)	0.0009 (13)	−0.0007 (13)
C18	0.0234 (15)	0.0287 (18)	0.0268 (16)	−0.0010 (14)	−0.0005 (13)	0.0012 (14)
C19	0.0275 (17)	0.041 (2)	0.0236 (16)	−0.0071 (15)	0.0018 (13)	0.0039 (15)
C20	0.0226 (16)	0.041 (2)	0.0366 (18)	−0.0029 (15)	0.0030 (14)	−0.0046 (17)
C21	0.0287 (17)	0.0303 (19)	0.0391 (19)	−0.0008 (15)	0.0029 (15)	−0.0027 (16)
C22	0.0254 (15)	0.0305 (17)	0.0295 (16)	−0.0029 (14)	0.0019 (13)	0.0026 (15)
N1	0.0259 (14)	0.0250 (14)	0.0249 (13)	−0.0059 (11)	0.0036 (11)	−0.0022 (11)
O1	0.0310 (12)	0.0333 (14)	0.0261 (12)	0.0019 (11)	0.0031 (10)	0.0028 (10)
F1	0.0352 (11)	0.0316 (11)	0.0356 (11)	0.0002 (9)	0.0069 (9)	0.0073 (9)
F2	0.0343 (11)	0.0526 (15)	0.0332 (11)	−0.0021 (10)	0.0082 (9)	0.0095 (10)
F3	0.0545 (13)	0.0228 (10)	0.0332 (11)	0.0008 (10)	0.0035 (10)	−0.0042 (8)
F4	0.0503 (13)	0.0273 (11)	0.0366 (12)	0.0009 (9)	0.0013 (10)	0.0051 (9)

Geometric parameters (Å, º)

C1—H1	1	C10—O1	1.437 (5)
C1—C8	1.515 (4)	C11—C12	1.400 (5)
C1—C17	1.540 (5)	C11—C16	1.396 (5)
C1—N1	1.488 (4)	C11—N1	1.423 (4)
C2—H2A	0.99	C12—C13	1.380 (5)
C2—H2B	0.99	C12—F3	1.348 (4)
C2—C3	1.519 (5)	C13—C14	1.368 (5)
C2—N1	1.461 (4)	C13—F4	1.350 (4)
C3—H3A	0.99	C14—H14	0.95
C3—H3B	0.99	C14—C15	1.391 (5)
C3—C9	1.498 (5)	C15—H15	0.95
C4—H4	0.95	C15—C16	1.380 (5)
C4—C5	1.386 (5)	C16—H16	0.95
C4—C9	1.397 (4)	C17—C18	1.382 (5)
C5—C6	1.396 (5)	C17—C22	1.389 (5)
C5—O1	1.361 (4)	C18—C19	1.372 (5)
C6—H6	0.95	C18—F1	1.361 (4)
C6—C7	1.382 (5)	C19—C20	1.381 (6)
C7—H7	0.95	C19—F2	1.346 (4)
C7—C8	1.401 (5)	C20—H20	0.95
C8—C9	1.393 (5)	C20—C21	1.393 (5)
C10—H10A	0.98	C21—H21	0.95
C10—H10B	0.98	C21—C22	1.394 (5)
C10—H10C	0.98	C22—H22	0.95
C8—C1—H1	107.8	O1—C10—H10C	109.5
C8—C1—C17	111.9 (3)	C12—C11—N1	118.5 (3)
C17—C1—H1	107.8	C16—C11—C12	116.5 (3)
N1—C1—H1	107.8	C16—C11—N1	124.9 (3)
N1—C1—C8	110.9 (3)	C13—C12—C11	121.3 (3)
N1—C1—C17	110.5 (3)	F3—C12—C11	119.9 (3)
H2A—C2—H2B	108.2	F3—C12—C13	118.8 (3)
C3—C2—H2A	109.8	C14—C13—C12	121.7 (3)
C3—C2—H2B	109.8	F4—C13—C12	117.9 (3)
N1—C2—H2A	109.8	F4—C13—C14	120.4 (3)
N1—C2—H2B	109.8	C13—C14—H14	121
N1—C2—C3	109.4 (3)	C13—C14—C15	118.0 (3)
C2—C3—H3A	109.1	C15—C14—H14	121
C2—C3—H3B	109.1	C14—C15—H15	119.6
H3A—C3—H3B	107.9	C16—C15—C14	120.9 (3)
C9—C3—C2	112.3 (3)	C16—C15—H15	119.6
C9—C3—H3A	109.1	C11—C16—H16	119.2
C9—C3—H3B	109.1	C15—C16—C11	121.6 (3)
C5—C4—H4	119.5	C15—C16—H16	119.2
C5—C4—C9	120.9 (3)	C18—C17—C1	120.3 (3)
C9—C4—H4	119.5	C18—C17—C22	116.6 (3)
C4—C5—C6	119.4 (3)	C22—C17—C1	122.9 (3)
O1—C5—C4	124.5 (3)	C19—C18—C17	122.7 (3)
O1—C5—C6	116.1 (3)	F1—C18—C17	119.5 (3)
C5—C6—H6	120	F1—C18—C19	117.8 (3)
C7—C6—C5	120.0 (3)	C18—C19—C20	120.7 (3)
C7—C6—H6	120	F2—C19—C18	119.2 (3)
C6—C7—H7	119.6	F2—C19—C20	120.1 (3)
C6—C7—C8	120.8 (3)	C19—C20—H20	121
C8—C7—H7	119.6	C19—C20—C21	118.0 (3)
C7—C8—C1	118.6 (3)	C21—C20—H20	121
C9—C8—C1	122.1 (3)	C20—C21—H21	119.8
C9—C8—C7	119.3 (3)	C20—C21—C22	120.4 (4)
C4—C9—C3	119.6 (3)	C22—C21—H21	119.8
C8—C9—C3	120.8 (3)	C17—C22—C21	121.4 (3)
C8—C9—C4	119.6 (3)	C17—C22—H22	119.3
H10A—C10—H10B	109.5	C21—C22—H22	119.3
H10A—C10—H10C	109.5	C2—N1—C1	113.7 (3)
H10B—C10—H10C	109.5	C11—N1—C1	114.2 (3)
O1—C10—H10A	109.5	C11—N1—C2	113.8 (3)
O1—C10—H10B	109.5	C5—O1—C10	116.3 (3)
C1—C8—C9—C3	−5.1 (5)	C14—C15—C16—C11	1.5 (5)
C1—C8—C9—C4	175.9 (3)	C16—C11—C12—C13	0.8 (5)
C1—C17—C18—C19	−172.8 (3)	C16—C11—C12—F3	178.9 (3)
C1—C17—C18—F1	7.1 (4)	C16—C11—N1—C1	109.2 (4)
C1—C17—C22—C21	171.7 (3)	C16—C11—N1—C2	−23.6 (5)
C2—C3—C9—C4	−160.0 (3)	C17—C1—C8—C7	69.9 (4)
C2—C3—C9—C8	21.1 (5)	C17—C1—C8—C9	−107.1 (4)
C3—C2—N1—C1	64.7 (4)	C17—C1—N1—C2	77.6 (3)
C3—C2—N1—C11	−162.3 (3)	C17—C1—N1—C11	−55.2 (4)
C4—C5—C6—C7	−2.4 (5)	C17—C18—C19—C20	−0.4 (5)
C4—C5—O1—C10	6.4 (5)	C17—C18—C19—F2	−179.2 (3)
C5—C4—C9—C3	−178.6 (3)	C18—C17—C22—C21	−3.8 (5)
C5—C4—C9—C8	0.4 (5)	C18—C19—C20—C21	−1.2 (5)
C5—C6—C7—C8	1.8 (5)	C19—C20—C21—C22	0.2 (5)
C6—C5—O1—C10	−173.5 (3)	C20—C21—C22—C17	2.3 (5)
C6—C7—C8—C1	−177.1 (3)	C22—C17—C18—C19	2.8 (5)
C6—C7—C8—C9	−0.1 (5)	C22—C17—C18—F1	−177.3 (3)
C7—C8—C9—C3	178.0 (3)	N1—C1—C8—C7	−166.3 (3)
C7—C8—C9—C4	−1.0 (5)	N1—C1—C8—C9	16.8 (4)
C8—C1—C17—C18	−142.5 (3)	N1—C1—C17—C18	93.5 (4)
C8—C1—C17—C22	42.2 (4)	N1—C1—C17—C22	−81.9 (4)
C8—C1—N1—C2	−47.0 (4)	N1—C2—C3—C9	−49.1 (4)
C8—C1—N1—C11	−179.9 (3)	N1—C11—C12—C13	−176.2 (3)
C9—C4—C5—C6	1.3 (5)	N1—C11—C12—F3	2.0 (5)
C9—C4—C5—O1	−178.6 (3)	N1—C11—C16—C15	175.0 (3)
C11—C12—C13—C14	0.5 (5)	O1—C5—C6—C7	177.5 (3)
C11—C12—C13—F4	179.3 (3)	F1—C18—C19—C20	179.7 (3)
C12—C11—C16—C15	−1.8 (5)	F1—C18—C19—F2	0.9 (5)
C12—C11—N1—C1	−74.1 (4)	F2—C19—C20—C21	177.6 (3)
C12—C11—N1—C2	153.1 (3)	F3—C12—C13—C14	−177.7 (3)
C12—C13—C14—C15	−0.8 (5)	F3—C12—C13—F4	1.1 (5)
C13—C14—C15—C16	−0.1 (5)	F4—C13—C14—C15	−179.6 (3)

(6-2)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.449 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 4466 reflections
a = 9.705 (3) Å	θ = 2.1–27.5°
b = 13.476 (3) Å	µ = 0.12 mm^−1
c = 13.843 (4) Å	T = 100 K
β = 101.159 (11)°	Block, clear light colourless
V = 1776.2 (8) Å^3	0.22 × 0.2 × 0.18 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3065 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.059
profile data from ω–scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan Blessing 1995	h = −12→12
Tmin = 0.908, Tmax = 1	k = −17→17
11947 measured reflections	l = −16→17
4037 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0647P)^2 + 0.425P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4037 reflections	Δρmax = 0.29 e Å^−3
254 parameters	Δρmin = −0.24 e Å^−3

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
C1	−0.08483 (17)	0.86709 (12)	0.33681 (12)	0.0190 (3)
H1	0.0063	0.8992	0.367	0.023*
C2	−0.18494 (17)	0.70394 (12)	0.28595 (12)	0.0215 (3)
H2A	−0.1634	0.6381	0.2608	0.026*
H2B	−0.2502	0.7389	0.233	0.026*
C3	−0.25218 (18)	0.69158 (12)	0.37575 (13)	0.0236 (4)
H3A	−0.3476	0.6636	0.3549	0.028*
H3B	−0.1961	0.644	0.4219	0.028*
C4	−0.34982 (17)	0.79782 (13)	0.49695 (12)	0.0225 (4)
H4	−0.4059	0.7429	0.5084	0.027*
C5	−0.35645 (17)	0.88567 (13)	0.54850 (12)	0.0222 (4)
C6	−0.27544 (18)	0.96715 (13)	0.53257 (13)	0.0237 (4)
H6	−0.2793	1.0271	0.568	0.028*
C7	−0.18863 (17)	0.95902 (12)	0.46368 (12)	0.0220 (3)
H7	−0.1342	1.0146	0.4515	0.026*
C8	−0.17991 (17)	0.87065 (12)	0.41198 (11)	0.0194 (3)
C9	−0.26194 (16)	0.78927 (12)	0.42859 (12)	0.0198 (3)
C17	−0.14755 (17)	0.92530 (12)	0.24323 (12)	0.0200 (3)
C18	−0.06224 (18)	0.97450 (12)	0.18894 (13)	0.0232 (4)
C19	−0.1120 (2)	1.02610 (13)	0.10241 (14)	0.0284 (4)
H19	−0.0506	1.0602	0.068	0.034*
C20	−0.2550 (2)	1.02522 (13)	0.06923 (13)	0.0295 (4)
C21	−0.3468 (2)	0.97771 (13)	0.11817 (13)	0.0277 (4)
H21	−0.4451	0.9785	0.0931	0.033*
C22	−0.29141 (18)	0.92853 (13)	0.20552 (12)	0.0233 (4)
H22	−0.3536	0.8962	0.2405	0.028*
C11	0.04462 (17)	0.75126 (12)	0.25222 (12)	0.0194 (3)
C12	0.18607 (18)	0.76408 (12)	0.29222 (12)	0.0218 (4)
C13	0.28775 (18)	0.75549 (13)	0.23544 (13)	0.0248 (4)
C14	0.25281 (19)	0.73385 (13)	0.13594 (13)	0.0252 (4)
H14	0.3231	0.7279	0.0971	0.03*
C15	0.11169 (19)	0.72117 (13)	0.09480 (13)	0.0246 (4)
H15	0.0848	0.7068	0.0266	0.03*
C16	0.00940 (18)	0.72914 (12)	0.15176 (12)	0.0229 (4)
H16	−0.0864	0.7194	0.122	0.028*
C10	−0.4520 (2)	0.97158 (14)	0.67227 (14)	0.0301 (4)
H10A	−0.4839	1.028	0.629	0.045*
H10B	−0.3583	0.9857	0.7109	0.045*
H10C	−0.5177	0.9607	0.7168	0.045*
N1	−0.05506 (15)	0.76170 (10)	0.31508 (10)	0.0197 (3)
O1	−0.44620 (13)	0.88456 (10)	0.61407 (9)	0.0283 (3)
F3	0.07894 (11)	0.97360 (8)	0.22225 (8)	0.0300 (3)
F4	−0.30735 (14)	1.07384 (10)	−0.01634 (9)	0.0447 (3)
F1	0.22781 (11)	0.78603 (8)	0.38935 (7)	0.0294 (3)
F2	0.42376 (11)	0.76888 (9)	0.27916 (8)	0.0367 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0180 (8)	0.0216 (7)	0.0175 (8)	−0.0016 (6)	0.0035 (6)	−0.0020 (6)
C2	0.0197 (8)	0.0220 (8)	0.0226 (8)	−0.0021 (6)	0.0036 (7)	−0.0029 (6)
C3	0.0213 (8)	0.0230 (8)	0.0271 (9)	−0.0021 (6)	0.0061 (7)	−0.0007 (7)
C4	0.0181 (8)	0.0281 (8)	0.0213 (8)	−0.0006 (6)	0.0037 (7)	0.0032 (7)
C5	0.0175 (8)	0.0334 (9)	0.0159 (8)	0.0055 (7)	0.0040 (7)	0.0017 (7)
C6	0.0214 (8)	0.0280 (9)	0.0213 (8)	0.0024 (7)	0.0029 (7)	−0.0045 (7)
C7	0.0203 (8)	0.0256 (8)	0.0196 (8)	−0.0009 (6)	0.0025 (7)	−0.0001 (6)
C8	0.0176 (8)	0.0235 (8)	0.0163 (7)	0.0018 (6)	0.0016 (6)	0.0016 (6)
C9	0.0151 (8)	0.0266 (8)	0.0166 (8)	0.0026 (6)	0.0002 (6)	0.0014 (6)
C17	0.0215 (8)	0.0201 (7)	0.0189 (8)	0.0015 (6)	0.0051 (7)	−0.0020 (6)
C18	0.0227 (9)	0.0230 (8)	0.0241 (9)	−0.0022 (6)	0.0049 (7)	−0.0016 (7)
C19	0.0342 (10)	0.0265 (9)	0.0263 (9)	−0.0051 (7)	0.0103 (8)	0.0031 (7)
C20	0.0382 (11)	0.0287 (9)	0.0200 (9)	0.0017 (7)	0.0015 (8)	0.0056 (7)
C21	0.0241 (9)	0.0339 (9)	0.0232 (9)	0.0022 (7)	−0.0004 (7)	0.0024 (7)
C22	0.0226 (9)	0.0260 (8)	0.0215 (8)	0.0009 (6)	0.0047 (7)	−0.0001 (7)
C11	0.0187 (8)	0.0203 (7)	0.0199 (8)	0.0024 (6)	0.0052 (7)	0.0016 (6)
C12	0.0209 (9)	0.0266 (8)	0.0172 (8)	0.0021 (6)	0.0020 (7)	−0.0008 (6)
C13	0.0156 (8)	0.0322 (9)	0.0262 (9)	0.0010 (7)	0.0031 (7)	−0.0003 (7)
C14	0.0239 (9)	0.0301 (9)	0.0235 (9)	0.0006 (7)	0.0093 (7)	−0.0014 (7)
C15	0.0255 (9)	0.0300 (9)	0.0185 (8)	0.0007 (7)	0.0047 (7)	−0.0026 (7)
C16	0.0201 (8)	0.0267 (8)	0.0213 (8)	−0.0005 (6)	0.0023 (7)	−0.0010 (7)
C10	0.0290 (10)	0.0389 (10)	0.0240 (9)	0.0096 (8)	0.0091 (8)	−0.0011 (8)
N1	0.0175 (7)	0.0206 (7)	0.0216 (7)	−0.0005 (5)	0.0051 (6)	−0.0014 (5)
O1	0.0243 (6)	0.0371 (7)	0.0261 (6)	0.0037 (5)	0.0113 (5)	−0.0003 (5)
F3	0.0208 (5)	0.0323 (6)	0.0371 (6)	−0.0048 (4)	0.0058 (5)	0.0053 (4)
F4	0.0474 (7)	0.0517 (8)	0.0312 (6)	−0.0041 (6)	−0.0021 (6)	0.0203 (5)
F1	0.0223 (5)	0.0471 (6)	0.0175 (5)	0.0004 (4)	0.0009 (4)	−0.0051 (4)
F2	0.0159 (5)	0.0616 (8)	0.0318 (6)	−0.0002 (5)	0.0027 (5)	−0.0051 (5)

Geometric parameters (Å, º)

C1—H1	1	C18—F3	1.358 (2)
C1—C8	1.519 (2)	C19—H19	0.95
C1—C17	1.536 (2)	C19—C20	1.376 (3)
C1—N1	1.491 (2)	C20—C21	1.377 (3)
C2—H2A	0.99	C20—F4	1.363 (2)
C2—H2B	0.99	C21—H21	0.95
C2—C3	1.521 (2)	C21—C22	1.392 (2)
C2—N1	1.470 (2)	C22—H22	0.95
C3—H3A	0.99	C11—C12	1.388 (2)
C3—H3B	0.99	C11—C16	1.398 (2)
C3—C9	1.518 (2)	C11—N1	1.428 (2)
C4—H4	0.95	C12—C13	1.380 (2)
C4—C5	1.390 (2)	C12—F1	1.3596 (19)
C4—C9	1.396 (2)	C13—C14	1.384 (3)
C5—C6	1.393 (2)	C13—F2	1.354 (2)
C5—O1	1.3744 (19)	C14—H14	0.95
C6—H6	0.95	C14—C15	1.388 (3)
C6—C7	1.394 (2)	C15—H15	0.95
C7—H7	0.95	C15—C16	1.386 (2)
C7—C8	1.400 (2)	C16—H16	0.95
C8—C9	1.400 (2)	C10—H10A	0.98
C17—C18	1.389 (2)	C10—H10B	0.98
C17—C22	1.393 (2)	C10—H10C	0.98
C18—C19	1.388 (3)	C10—O1	1.430 (2)
C8—C1—H1	107.8	F3—C18—C19	117.17 (15)
C8—C1—C17	111.56 (13)	C18—C19—H19	121.8
C17—C1—H1	107.8	C20—C19—C18	116.34 (16)
N1—C1—H1	107.8	C20—C19—H19	121.8
N1—C1—C8	109.59 (12)	C19—C20—C21	123.15 (16)
N1—C1—C17	112.14 (13)	F4—C20—C19	117.92 (16)
H2A—C2—H2B	108.4	F4—C20—C21	118.93 (17)
C3—C2—H2A	110	C20—C21—H21	120.9
C3—C2—H2B	110	C20—C21—C22	118.10 (17)
N1—C2—H2A	110	C22—C21—H21	120.9
N1—C2—H2B	110	C17—C22—H22	119
N1—C2—C3	108.33 (13)	C21—C22—C17	122.04 (16)
C2—C3—H3A	109.2	C21—C22—H22	119
C2—C3—H3B	109.2	C12—C11—C16	117.11 (15)
H3A—C3—H3B	107.9	C12—C11—N1	118.62 (15)
C9—C3—C2	112.06 (13)	C16—C11—N1	124.27 (15)
C9—C3—H3A	109.2	C13—C12—C11	121.55 (15)
C9—C3—H3B	109.2	F1—C12—C11	120.27 (14)
C5—C4—H4	119.6	F1—C12—C13	118.19 (15)
C5—C4—C9	120.89 (15)	C12—C13—C14	121.32 (16)
C9—C4—H4	119.6	F2—C13—C12	118.49 (15)
C4—C5—C6	120.43 (15)	F2—C13—C14	120.19 (15)
O1—C5—C4	115.34 (15)	C13—C14—H14	121.1
O1—C5—C6	124.23 (15)	C13—C14—C15	117.79 (15)
C5—C6—H6	120.6	C15—C14—H14	121.1
C5—C6—C7	118.74 (15)	C14—C15—H15	119.5
C7—C6—H6	120.6	C16—C15—C14	121.02 (16)
C6—C7—H7	119.3	C16—C15—H15	119.5
C6—C7—C8	121.39 (15)	C11—C16—H16	119.4
C8—C7—H7	119.3	C15—C16—C11	121.20 (16)
C7—C8—C1	118.80 (14)	C15—C16—H16	119.4
C9—C8—C1	121.85 (14)	H10A—C10—H10B	109.5
C9—C8—C7	119.32 (14)	H10A—C10—H10C	109.5
C4—C9—C3	120.11 (15)	H10B—C10—H10C	109.5
C4—C9—C8	119.21 (15)	O1—C10—H10A	109.5
C8—C9—C3	120.65 (14)	O1—C10—H10B	109.5
C18—C17—C1	121.30 (15)	O1—C10—H10C	109.5
C18—C17—C22	116.19 (15)	C2—N1—C1	111.73 (13)
C22—C17—C1	122.46 (14)	C11—N1—C1	113.41 (12)
C19—C18—C17	124.16 (17)	C11—N1—C2	115.26 (13)
F3—C18—C17	118.66 (15)	C5—O1—C10	117.53 (14)
C1—C8—C9—C3	3.6 (2)	C18—C19—C20—F4	−179.00 (16)
C1—C8—C9—C4	−178.47 (15)	C19—C20—C21—C22	0.2 (3)
C1—C17—C18—C19	178.19 (16)	C20—C21—C22—C17	−0.8 (3)
C1—C17—C18—F3	−2.5 (2)	C22—C17—C18—C19	0.8 (2)
C1—C17—C22—C21	−176.98 (15)	C22—C17—C18—F3	−179.90 (14)
C2—C3—C9—C4	164.28 (15)	C11—C12—C13—C14	0.1 (3)
C2—C3—C9—C8	−17.8 (2)	C11—C12—C13—F2	−179.97 (15)
C3—C2—N1—C1	−69.58 (16)	C12—C11—C16—C15	−0.5 (2)
C3—C2—N1—C11	159.04 (13)	C12—C11—N1—C1	77.52 (18)
C4—C5—C6—C7	0.4 (2)	C12—C11—N1—C2	−151.91 (15)
C4—C5—O1—C10	177.17 (15)	C12—C13—C14—C15	0.1 (3)
C5—C4—C9—C3	177.78 (15)	C13—C14—C15—C16	−0.5 (3)
C5—C4—C9—C8	−0.1 (2)	C14—C15—C16—C11	0.7 (3)
C5—C6—C7—C8	−1.1 (3)	C16—C11—C12—C13	0.0 (2)
C6—C5—O1—C10	−2.6 (2)	C16—C11—C12—F1	179.80 (15)
C6—C7—C8—C1	179.15 (15)	C16—C11—N1—C1	−102.20 (18)
C6—C7—C8—C9	1.1 (2)	C16—C11—N1—C2	28.4 (2)
C7—C8—C9—C3	−178.41 (15)	N1—C1—C8—C7	161.86 (14)
C7—C8—C9—C4	−0.5 (2)	N1—C1—C8—C9	−20.2 (2)
C8—C1—C17—C18	147.32 (15)	N1—C1—C17—C18	−89.31 (18)
C8—C1—C17—C22	−35.5 (2)	N1—C1—C17—C22	87.88 (18)
C8—C1—N1—C2	53.40 (17)	N1—C2—C3—C9	48.80 (18)
C8—C1—N1—C11	−174.28 (13)	N1—C11—C12—C13	−179.69 (15)
C9—C4—C5—C6	0.2 (2)	N1—C11—C12—F1	0.1 (2)
C9—C4—C5—O1	−179.63 (14)	N1—C11—C16—C15	179.26 (15)
C17—C1—C8—C7	−73.34 (18)	O1—C5—C6—C7	−179.79 (15)
C17—C1—C8—C9	104.64 (17)	F3—C18—C19—C20	179.27 (15)
C17—C1—N1—C2	−71.06 (16)	F4—C20—C21—C22	−179.93 (16)
C17—C1—N1—C11	61.26 (18)	F1—C12—C13—C14	−179.63 (16)
C17—C18—C19—C20	−1.4 (3)	F1—C12—C13—F2	0.3 (2)
C18—C17—C22—C21	0.3 (2)	F2—C13—C14—C15	−179.79 (15)
C18—C19—C20—C21	0.9 (3)

(6-3)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.463 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4679 reflections
a = 9.642 (2) Å	θ = 3.1–27.5°
b = 13.292 (2) Å	µ = 0.12 mm^−1
c = 13.931 (3) Å	T = 100 K
β = 99.890 (9)°	Prism, clear light colourless
V = 1758.9 (6) Å^3	0.3 × 0.2 × 0.15 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2773 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.029
profile data from ω–scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −11→11
Tmin = 0.873, Tmax = 1	k = −15→15
14416 measured reflections	l = −16→16
3089 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 0.4956P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3089 reflections	Δρmax = 0.27 e Å^−3
254 parameters	Δρmin = −0.24 e Å^−3

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
C1	0.42509 (14)	0.12556 (10)	0.32106 (10)	0.0175 (3)
H1	0.5168	0.0935	0.3494	0.021*
C2	0.32303 (14)	0.28884 (11)	0.26580 (11)	0.0202 (3)
H2A	0.2575	0.2514	0.2159	0.024*
H2B	0.344	0.3545	0.2379	0.024*
C3	0.25684 (15)	0.30489 (11)	0.35616 (11)	0.0214 (3)
H3A	0.3123	0.3557	0.3984	0.026*
H3B	0.1604	0.3317	0.3363	0.026*
C4	0.16258 (14)	0.20363 (11)	0.48281 (10)	0.0200 (3)
H4	0.1066	0.2601	0.4933	0.024*
C5	0.15577 (14)	0.11642 (11)	0.53704 (10)	0.0203 (3)
C6	0.23754 (15)	0.03310 (11)	0.52300 (10)	0.0215 (3)
H6	0.2341	−0.0264	0.5603	0.026*
C7	0.32404 (14)	0.03893 (11)	0.45334 (10)	0.0196 (3)
H7	0.3789	−0.018	0.4424	0.024*
C8	0.33269 (14)	0.12601 (10)	0.39896 (10)	0.0180 (3)
C9	0.25018 (14)	0.20928 (11)	0.41347 (10)	0.0185 (3)
C17	0.35827 (14)	0.06318 (10)	0.23255 (10)	0.0192 (3)
C18	0.43866 (15)	0.01454 (11)	0.17321 (11)	0.0215 (3)
C19	0.38237 (17)	−0.04163 (12)	0.09206 (11)	0.0269 (3)
H19	0.4424	−0.0739	0.0541	0.032*
C20	0.23736 (17)	−0.05019 (12)	0.06694 (11)	0.0281 (4)
H20	0.1955	−0.0878	0.0115	0.034*
C21	0.15609 (16)	−0.00228 (12)	0.12522 (11)	0.0251 (3)
C22	0.21262 (15)	0.05384 (11)	0.20594 (10)	0.0216 (3)
H22	0.1521	0.0862	0.2435	0.026*
C11	0.55496 (14)	0.24037 (10)	0.23227 (10)	0.0177 (3)
C12	0.69652 (15)	0.22646 (11)	0.27165 (10)	0.0194 (3)
C13	0.79948 (15)	0.23524 (11)	0.21477 (11)	0.0222 (3)
C14	0.76698 (16)	0.25832 (11)	0.11690 (11)	0.0237 (3)
H14	0.8387	0.2648	0.0783	0.028*
C15	0.62626 (16)	0.27186 (11)	0.07646 (11)	0.0227 (3)
H15	0.6011	0.287	0.0091	0.027*
C16	0.52201 (15)	0.26352 (11)	0.13324 (11)	0.0206 (3)
H16	0.4265	0.2737	0.1042	0.025*
C10	0.05768 (16)	0.03307 (12)	0.66242 (11)	0.0270 (4)
H10A	0.0256	−0.0249	0.621	0.041*
H10B	−0.0087	0.0457	0.707	0.041*
H10C	0.1512	0.019	0.7001	0.041*
N1	0.45407 (12)	0.23104 (9)	0.29489 (9)	0.0182 (3)
O1	0.06491 (11)	0.11996 (8)	0.60256 (7)	0.0250 (3)
F3	0.58141 (9)	0.02063 (6)	0.19661 (7)	0.0270 (2)
F4	0.01399 (9)	−0.01197 (8)	0.10368 (7)	0.0356 (3)
F1	0.73577 (8)	0.20300 (7)	0.36713 (6)	0.0249 (2)
F2	0.93510 (9)	0.22066 (8)	0.25809 (7)	0.0326 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0161 (7)	0.0167 (7)	0.0199 (7)	0.0008 (5)	0.0034 (5)	0.0032 (5)
C2	0.0173 (7)	0.0194 (7)	0.0242 (7)	0.0024 (5)	0.0038 (6)	0.0038 (6)
C3	0.0180 (7)	0.0199 (7)	0.0270 (8)	0.0030 (6)	0.0056 (6)	0.0017 (6)
C4	0.0147 (7)	0.0234 (7)	0.0216 (7)	0.0013 (6)	0.0017 (5)	−0.0011 (6)
C5	0.0156 (7)	0.0288 (8)	0.0164 (7)	−0.0041 (6)	0.0027 (5)	−0.0017 (6)
C6	0.0209 (7)	0.0234 (7)	0.0196 (7)	−0.0030 (6)	0.0016 (6)	0.0039 (6)
C7	0.0175 (7)	0.0201 (7)	0.0204 (7)	0.0010 (5)	0.0009 (5)	0.0004 (5)
C8	0.0152 (7)	0.0217 (7)	0.0162 (7)	−0.0014 (5)	0.0000 (5)	−0.0002 (5)
C9	0.0150 (7)	0.0214 (7)	0.0180 (7)	−0.0013 (5)	−0.0006 (5)	0.0000 (5)
C17	0.0216 (7)	0.0170 (7)	0.0195 (7)	0.0001 (6)	0.0051 (6)	0.0038 (5)
C18	0.0191 (7)	0.0192 (7)	0.0269 (8)	0.0004 (6)	0.0056 (6)	0.0020 (6)
C19	0.0316 (8)	0.0241 (8)	0.0266 (8)	0.0007 (6)	0.0097 (6)	−0.0035 (6)
C20	0.0330 (9)	0.0282 (8)	0.0227 (8)	−0.0063 (7)	0.0036 (6)	−0.0048 (6)
C21	0.0209 (8)	0.0323 (8)	0.0219 (8)	−0.0056 (6)	0.0029 (6)	0.0020 (6)
C22	0.0216 (7)	0.0248 (8)	0.0197 (7)	−0.0018 (6)	0.0067 (6)	0.0017 (6)
C11	0.0184 (7)	0.0144 (7)	0.0214 (7)	−0.0018 (5)	0.0064 (6)	−0.0008 (5)
C12	0.0212 (7)	0.0206 (7)	0.0162 (7)	−0.0012 (6)	0.0026 (6)	0.0012 (5)
C13	0.0147 (7)	0.0245 (8)	0.0272 (8)	−0.0012 (6)	0.0029 (6)	−0.0010 (6)
C14	0.0231 (8)	0.0243 (8)	0.0261 (8)	−0.0023 (6)	0.0110 (6)	−0.0002 (6)
C15	0.0273 (8)	0.0226 (7)	0.0188 (7)	0.0000 (6)	0.0057 (6)	0.0020 (6)
C16	0.0184 (7)	0.0206 (7)	0.0226 (7)	0.0002 (6)	0.0028 (6)	0.0005 (6)
C10	0.0258 (8)	0.0333 (9)	0.0230 (8)	−0.0086 (7)	0.0074 (6)	0.0018 (6)
N1	0.0170 (6)	0.0175 (6)	0.0209 (6)	0.0012 (5)	0.0056 (5)	0.0025 (5)
O1	0.0224 (5)	0.0306 (6)	0.0243 (6)	−0.0022 (4)	0.0103 (4)	0.0027 (4)
F3	0.0188 (5)	0.0260 (5)	0.0373 (5)	0.0032 (3)	0.0077 (4)	−0.0046 (4)
F4	0.0223 (5)	0.0567 (7)	0.0268 (5)	−0.0116 (4)	0.0018 (4)	−0.0061 (4)
F1	0.0204 (4)	0.0341 (5)	0.0195 (4)	0.0008 (4)	0.0016 (3)	0.0038 (3)
F2	0.0150 (4)	0.0492 (6)	0.0333 (5)	0.0003 (4)	0.0034 (4)	0.0038 (4)

Geometric parameters (Å, º)

C1—H1	1	C18—F3	1.3613 (17)
C1—C8	1.5178 (18)	C19—H19	0.95
C1—C17	1.5329 (19)	C19—C20	1.386 (2)
C1—N1	1.4871 (17)	C20—H20	0.95
C2—H2A	0.99	C20—C21	1.377 (2)
C2—H2B	0.99	C21—C22	1.381 (2)
C2—C3	1.521 (2)	C21—F4	1.3574 (18)
C2—N1	1.4748 (18)	C22—H22	0.95
C3—H3A	0.99	C11—C12	1.393 (2)
C3—H3B	0.99	C11—C16	1.396 (2)
C3—C9	1.508 (2)	C11—N1	1.4192 (18)
C4—H4	0.95	C12—C13	1.377 (2)
C4—C5	1.391 (2)	C12—F1	1.3553 (16)
C4—C9	1.390 (2)	C13—C14	1.380 (2)
C5—C6	1.393 (2)	C13—F2	1.3567 (17)
C5—O1	1.3703 (17)	C14—H14	0.95
C6—H6	0.95	C14—C15	1.389 (2)
C6—C7	1.386 (2)	C15—H15	0.95
C7—H7	0.95	C15—C16	1.386 (2)
C7—C8	1.394 (2)	C16—H16	0.95
C8—C9	1.398 (2)	C10—H10A	0.98
C17—C18	1.387 (2)	C10—H10B	0.98
C17—C22	1.395 (2)	C10—H10C	0.98
C18—C19	1.385 (2)	C10—O1	1.4333 (18)
C8—C1—H1	107.9	F3—C18—C19	117.76 (13)
C8—C1—C17	111.10 (11)	C18—C19—H19	120.4
C17—C1—H1	107.9	C18—C19—C20	119.15 (14)
N1—C1—H1	107.9	C20—C19—H19	120.4
N1—C1—C8	109.25 (11)	C19—C20—H20	121.2
N1—C1—C17	112.56 (11)	C21—C20—C19	117.67 (14)
H2A—C2—H2B	108.4	C21—C20—H20	121.2
C3—C2—H2A	110.1	C20—C21—C22	123.00 (14)
C3—C2—H2B	110.1	F4—C21—C20	118.73 (13)
N1—C2—H2A	110.1	F4—C21—C22	118.25 (13)
N1—C2—H2B	110.1	C17—C22—H22	119.9
N1—C2—C3	107.88 (11)	C21—C22—C17	120.19 (13)
C2—C3—H3A	109.1	C21—C22—H22	119.9
C2—C3—H3B	109.1	C12—C11—C16	117.37 (13)
H3A—C3—H3B	107.8	C12—C11—N1	118.36 (13)
C9—C3—C2	112.46 (12)	C16—C11—N1	124.28 (13)
C9—C3—H3A	109.1	C13—C12—C11	121.09 (13)
C9—C3—H3B	109.1	F1—C12—C11	120.43 (12)
C5—C4—H4	119.6	F1—C12—C13	118.47 (13)
C9—C4—H4	119.6	C12—C13—C14	121.56 (14)
C9—C4—C5	120.88 (13)	F2—C13—C12	117.82 (13)
C4—C5—C6	120.38 (13)	F2—C13—C14	120.61 (13)
O1—C5—C4	115.35 (13)	C13—C14—H14	121
O1—C5—C6	124.27 (13)	C13—C14—C15	118.03 (13)
C5—C6—H6	120.8	C15—C14—H14	121
C7—C6—C5	118.50 (13)	C14—C15—H15	119.6
C7—C6—H6	120.8	C16—C15—C14	120.80 (14)
C6—C7—H7	119.1	C16—C15—H15	119.6
C6—C7—C8	121.75 (13)	C11—C16—H16	119.4
C8—C7—H7	119.1	C15—C16—C11	121.16 (13)
C7—C8—C1	118.86 (12)	C15—C16—H16	119.4
C7—C8—C9	119.37 (13)	H10A—C10—H10B	109.5
C9—C8—C1	121.67 (12)	H10A—C10—H10C	109.5
C4—C9—C3	119.98 (12)	H10B—C10—H10C	109.5
C4—C9—C8	119.11 (13)	O1—C10—H10A	109.5
C8—C9—C3	120.91 (12)	O1—C10—H10B	109.5
C18—C17—C1	122.07 (13)	O1—C10—H10C	109.5
C18—C17—C22	116.13 (13)	C2—N1—C1	111.73 (11)
C22—C17—C1	121.78 (12)	C11—N1—C1	114.24 (11)
C19—C18—C17	123.85 (14)	C11—N1—C2	115.52 (11)
F3—C18—C17	118.38 (13)	C5—O1—C10	117.41 (12)
C1—C8—C9—C3	−3.9 (2)	C19—C20—C21—C22	0.6 (2)
C1—C8—C9—C4	176.99 (12)	C19—C20—C21—F4	−178.14 (13)
C1—C17—C18—C19	−179.30 (13)	C20—C21—C22—C17	−0.8 (2)
C1—C17—C18—F3	1.9 (2)	C22—C17—C18—C19	−0.6 (2)
C1—C17—C22—C21	179.42 (13)	C22—C17—C18—F3	−179.42 (12)
C2—C3—C9—C4	−163.62 (12)	C11—C12—C13—C14	0.2 (2)
C2—C3—C9—C8	17.30 (19)	C11—C12—C13—F2	−179.99 (12)
C3—C2—N1—C1	69.64 (14)	C12—C11—C16—C15	0.3 (2)
C3—C2—N1—C11	−157.51 (12)	C12—C11—N1—C1	−75.28 (16)
C4—C5—C6—C7	−0.7 (2)	C12—C11—N1—C2	153.05 (13)
C4—C5—O1—C10	−177.99 (12)	C12—C13—C14—C15	−0.5 (2)
C5—C4—C9—C3	−179.46 (13)	C13—C14—C15—C16	0.7 (2)
C5—C4—C9—C8	−0.4 (2)	C14—C15—C16—C11	−0.6 (2)
C5—C6—C7—C8	1.2 (2)	C16—C11—C12—C13	0.0 (2)
C6—C5—O1—C10	2.1 (2)	C16—C11—C12—F1	−179.45 (12)
C6—C7—C8—C1	−177.53 (12)	C16—C11—N1—C1	105.27 (15)
C6—C7—C8—C9	−1.2 (2)	C16—C11—N1—C2	−26.41 (19)
C7—C8—C9—C3	179.88 (12)	N1—C1—C8—C7	−162.46 (12)
C7—C8—C9—C4	0.8 (2)	N1—C1—C8—C9	21.32 (17)
C8—C1—C17—C18	−151.38 (13)	N1—C1—C17—C18	85.75 (16)
C8—C1—C17—C22	29.98 (17)	N1—C1—C17—C22	−92.90 (15)
C8—C1—N1—C2	−54.61 (14)	N1—C2—C3—C9	−47.92 (16)
C8—C1—N1—C11	171.91 (11)	N1—C11—C12—C13	−179.52 (12)
C9—C4—C5—C6	0.3 (2)	N1—C11—C12—F1	1.06 (19)
C9—C4—C5—O1	−179.58 (12)	N1—C11—C16—C15	179.72 (13)
C17—C1—C8—C7	72.77 (15)	O1—C5—C6—C7	179.19 (13)
C17—C1—C8—C9	−103.44 (14)	F3—C18—C19—C20	179.30 (13)
C17—C1—N1—C2	69.30 (14)	F4—C21—C22—C17	177.99 (13)
C17—C1—N1—C11	−64.17 (15)	F1—C12—C13—C14	179.59 (13)
C17—C18—C19—C20	0.5 (2)	F1—C12—C13—F2	−0.6 (2)
C18—C17—C22—C21	0.7 (2)	F2—C13—C14—C15	179.65 (13)
C18—C19—C20—C21	−0.4 (2)

(6-4)

Crystal data

C22H17F4NO	F(000) = 400
Mr = 387.36	Dx = 1.492 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2710 reflections
a = 8.317 (3) Å	θ = 3.1–27.5°
b = 6.0774 (19) Å	µ = 0.12 mm^−1
c = 17.513 (6) Å	T = 100 K
β = 103.095 (13)°	Plate, clear light colourless
V = 862.2 (5) Å^3	0.2 × 0.2 × 0.2 mm
Z = 2

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3794 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.083
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −10→10
Tmin = 0.92, Tmax = 1	k = −7→7
8616 measured reflections	l = −22→22
3898 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0866P)^2 + 0.0275P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.40 e Å^−3
3898 reflections	Δρmin = −0.28 e Å^−3
254 parameters	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower.
1 restraint	Absolute structure parameter: 0.4 (6)

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
F1	0.7071 (2)	0.3569 (2)	0.80781 (8)	0.0274 (3)
F2	0.8323 (2)	0.2831 (3)	0.95967 (8)	0.0321 (4)
F3	0.28875 (17)	0.3616 (2)	0.83412 (7)	0.0215 (3)
F4	0.15793 (18)	1.0018 (2)	0.67868 (8)	0.0238 (3)
O1	0.14935 (19)	0.7716 (3)	0.38680 (8)	0.0186 (3)
N1	0.5307 (2)	0.7267 (3)	0.75044 (10)	0.0158 (4)
C1	0.3743 (2)	0.6129 (3)	0.71404 (11)	0.0143 (4)
H1	0.3937	0.4515	0.7226	0.017*
C2	0.5348 (3)	0.9584 (4)	0.72693 (12)	0.0182 (4)
H2A	0.6374	1.0288	0.7566	0.022*
H2B	0.4396	1.0381	0.7389	0.022*
C3	0.5276 (3)	0.9704 (4)	0.63894 (12)	0.0191 (4)
H3A	0.5066	1.1245	0.6211	0.023*
H3B	0.6361	0.9264	0.6295	0.023*
C4	0.3392 (3)	0.8662 (4)	0.51033 (12)	0.0168 (4)
H4	0.3861	0.9829	0.4865	0.02*
C5	0.2157 (3)	0.7372 (3)	0.46532 (12)	0.0161 (4)
C6	0.1501 (3)	0.5591 (4)	0.49899 (12)	0.0177 (4)
H6	0.0682	0.4676	0.4678	0.021*
C7	0.2069 (3)	0.5178 (3)	0.57902 (12)	0.0170 (4)
H7	0.1629	0.3974	0.6022	0.02*
C8	0.3278 (2)	0.6515 (3)	0.62562 (11)	0.0148 (4)
C9	0.3956 (3)	0.8249 (3)	0.59135 (12)	0.0152 (4)
C10	0.1910 (3)	0.9733 (4)	0.35462 (13)	0.0218 (4)
H10A	0.1264	0.9885	0.3007	0.033*
H10B	0.3089	0.9737	0.3548	0.033*
H10C	0.1664	1.0965	0.3862	0.033*
C11	0.5853 (2)	0.6930 (4)	0.83329 (12)	0.0167 (4)
C12	0.6749 (3)	0.5037 (4)	0.85966 (12)	0.0185 (4)
C13	0.7411 (3)	0.4665 (4)	0.93928 (13)	0.0209 (5)
C14	0.7195 (3)	0.6167 (4)	0.99515 (12)	0.0226 (5)
H14	0.7645	0.5909	1.0493	0.027*
C15	0.6302 (3)	0.8072 (5)	0.97009 (13)	0.0248 (5)
H15	0.6145	0.9134	1.0076	0.03*
C16	0.5627 (3)	0.8445 (4)	0.88993 (13)	0.0217 (5)
H16	0.5009	0.9746	0.8741	0.026*
C17	0.2345 (3)	0.6783 (4)	0.75435 (11)	0.0155 (4)
C18	0.1387 (3)	0.8681 (4)	0.73814 (12)	0.0180 (4)
C19	0.0234 (3)	0.9337 (4)	0.78008 (13)	0.0204 (4)
H19	−0.0381	1.0654	0.7669	0.025*
C20	0.0000 (3)	0.8029 (4)	0.84152 (13)	0.0219 (5)
H20	−0.0767	0.8465	0.8714	0.026*
C21	0.0889 (3)	0.6070 (4)	0.85981 (12)	0.0200 (4)
H21	0.0723	0.5145	0.9011	0.024*
C22	0.2019 (3)	0.5525 (4)	0.81561 (12)	0.0166 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0439 (9)	0.0177 (6)	0.0194 (6)	0.0029 (6)	0.0049 (6)	−0.0034 (5)
F2	0.0452 (9)	0.0251 (7)	0.0233 (7)	0.0070 (7)	0.0018 (6)	0.0059 (6)
F3	0.0239 (7)	0.0216 (6)	0.0196 (6)	0.0014 (5)	0.0062 (5)	0.0066 (5)
F4	0.0250 (7)	0.0241 (6)	0.0237 (6)	0.0051 (5)	0.0086 (5)	0.0086 (5)
O1	0.0191 (7)	0.0236 (8)	0.0124 (6)	−0.0011 (6)	0.0019 (6)	0.0012 (6)
N1	0.0155 (8)	0.0183 (8)	0.0124 (7)	−0.0036 (6)	0.0010 (6)	−0.0003 (6)
C1	0.0150 (9)	0.0150 (9)	0.0127 (8)	−0.0022 (7)	0.0030 (7)	−0.0003 (7)
C2	0.0202 (10)	0.0178 (10)	0.0157 (9)	−0.0039 (8)	0.0019 (7)	−0.0023 (8)
C3	0.0208 (10)	0.0213 (10)	0.0148 (9)	−0.0069 (8)	0.0028 (7)	0.0014 (8)
C4	0.0166 (10)	0.0197 (9)	0.0148 (9)	0.0002 (8)	0.0048 (7)	0.0016 (8)
C5	0.0170 (9)	0.0198 (10)	0.0120 (8)	0.0020 (7)	0.0044 (7)	−0.0010 (7)
C6	0.0165 (9)	0.0214 (10)	0.0147 (9)	−0.0024 (8)	0.0027 (7)	−0.0030 (8)
C7	0.0177 (10)	0.0183 (9)	0.0153 (9)	−0.0033 (7)	0.0044 (7)	−0.0011 (8)
C8	0.0147 (9)	0.0168 (9)	0.0125 (8)	−0.0020 (7)	0.0024 (7)	−0.0003 (7)
C9	0.0143 (9)	0.0169 (9)	0.0143 (9)	−0.0022 (7)	0.0033 (7)	−0.0005 (7)
C10	0.0246 (11)	0.0244 (11)	0.0159 (9)	0.0018 (9)	0.0036 (8)	0.0054 (8)
C11	0.0131 (10)	0.0232 (10)	0.0137 (9)	−0.0032 (8)	0.0028 (7)	−0.0019 (8)
C12	0.0209 (10)	0.0186 (9)	0.0160 (9)	−0.0050 (8)	0.0044 (8)	−0.0029 (8)
C13	0.0213 (11)	0.0206 (10)	0.0206 (10)	−0.0029 (8)	0.0040 (8)	0.0024 (9)
C14	0.0193 (11)	0.0327 (12)	0.0147 (9)	−0.0022 (9)	0.0017 (8)	0.0012 (9)
C15	0.0222 (11)	0.0379 (13)	0.0136 (9)	0.0020 (10)	0.0023 (8)	−0.0058 (9)
C16	0.0186 (10)	0.0293 (11)	0.0163 (9)	0.0055 (9)	0.0019 (8)	−0.0018 (8)
C17	0.0141 (9)	0.0190 (9)	0.0130 (8)	−0.0030 (7)	0.0020 (7)	−0.0012 (7)
C18	0.0165 (10)	0.0210 (9)	0.0161 (9)	−0.0022 (8)	0.0028 (7)	0.0006 (8)
C19	0.0148 (10)	0.0226 (10)	0.0232 (10)	0.0004 (8)	0.0028 (8)	−0.0022 (8)
C20	0.0163 (10)	0.0300 (11)	0.0202 (9)	−0.0040 (9)	0.0057 (8)	−0.0075 (9)
C21	0.0187 (10)	0.0270 (11)	0.0146 (8)	−0.0059 (8)	0.0040 (7)	−0.0006 (9)
C22	0.0158 (9)	0.0185 (9)	0.0142 (8)	−0.0025 (8)	0.0005 (7)	−0.0003 (7)

Geometric parameters (Å, º)

F1—C12	1.343 (3)	C7—H7	0.95
F2—C13	1.350 (3)	C7—C8	1.402 (3)
F3—C22	1.366 (2)	C8—C9	1.394 (3)
F4—C18	1.358 (3)	C10—H10A	0.98
O1—C5	1.377 (2)	C10—H10B	0.98
O1—C10	1.425 (3)	C10—H10C	0.98
N1—C1	1.483 (3)	C11—C12	1.391 (3)
N1—C2	1.470 (3)	C11—C16	1.397 (3)
N1—C11	1.434 (3)	C12—C13	1.396 (3)
C1—H1	1	C13—C14	1.380 (3)
C1—C8	1.527 (3)	C14—H14	0.95
C1—C17	1.543 (3)	C14—C15	1.392 (4)
C2—H2A	0.99	C15—H15	0.95
C2—H2B	0.99	C15—C16	1.407 (3)
C2—C3	1.530 (3)	C16—H16	0.95
C3—H3A	0.99	C17—C18	1.394 (3)
C3—H3B	0.99	C17—C22	1.393 (3)
C3—C9	1.506 (3)	C18—C19	1.392 (3)
C4—H4	0.95	C19—H19	0.95
C4—C5	1.387 (3)	C19—C20	1.386 (3)
C4—C9	1.412 (3)	C20—H20	0.95
C5—C6	1.401 (3)	C20—C21	1.400 (3)
C6—H6	0.95	C21—H21	0.95
C6—C7	1.396 (3)	C21—C22	1.387 (3)
C5—O1—C10	116.58 (17)	O1—C10—H10B	109.5
C2—N1—C1	113.56 (17)	O1—C10—H10C	109.5
C11—N1—C1	114.47 (16)	H10A—C10—H10B	109.5
C11—N1—C2	113.46 (16)	H10A—C10—H10C	109.5
N1—C1—H1	107.3	H10B—C10—H10C	109.5
N1—C1—C8	111.12 (15)	C12—C11—N1	118.49 (19)
N1—C1—C17	111.22 (16)	C12—C11—C16	117.21 (19)
C8—C1—H1	107.3	C16—C11—N1	124.2 (2)
C8—C1—C17	112.36 (17)	F1—C12—C11	119.92 (19)
C17—C1—H1	107.3	F1—C12—C13	118.3 (2)
N1—C2—H2A	109.8	C11—C12—C13	121.7 (2)
N1—C2—H2B	109.8	F2—C13—C12	117.9 (2)
N1—C2—C3	109.25 (17)	F2—C13—C14	121.0 (2)
H2A—C2—H2B	108.3	C14—C13—C12	121.1 (2)
C3—C2—H2A	109.8	C13—C14—H14	120.9
C3—C2—H2B	109.8	C13—C14—C15	118.2 (2)
C2—C3—H3A	109	C15—C14—H14	120.9
C2—C3—H3B	109	C14—C15—H15	119.6
H3A—C3—H3B	107.8	C14—C15—C16	120.8 (2)
C9—C3—C2	112.73 (17)	C16—C15—H15	119.6
C9—C3—H3A	109	C11—C16—C15	121.0 (2)
C9—C3—H3B	109	C11—C16—H16	119.5
C5—C4—H4	119.8	C15—C16—H16	119.5
C5—C4—C9	120.34 (19)	C18—C17—C1	125.10 (18)
C9—C4—H4	119.8	C22—C17—C1	120.61 (19)
O1—C5—C4	124.01 (18)	C22—C17—C18	114.16 (18)
O1—C5—C6	115.56 (19)	F4—C18—C17	119.34 (18)
C4—C5—C6	120.42 (19)	F4—C18—C19	116.6 (2)
C5—C6—H6	120.5	C19—C18—C17	124.0 (2)
C7—C6—C5	119.05 (19)	C18—C19—H19	120.7
C7—C6—H6	120.5	C20—C19—C18	118.7 (2)
C6—C7—H7	119.5	C20—C19—H19	120.7
C6—C7—C8	121.01 (19)	C19—C20—H20	119.8
C8—C7—H7	119.5	C19—C20—C21	120.38 (19)
C7—C8—C1	119.01 (18)	C21—C20—H20	119.8
C9—C8—C1	121.24 (18)	C20—C21—H21	121.1
C9—C8—C7	119.63 (18)	C22—C21—C20	117.72 (19)
C4—C9—C3	119.10 (18)	C22—C21—H21	121.1
C8—C9—C3	121.42 (18)	F3—C22—C17	117.67 (18)
C8—C9—C4	119.49 (18)	F3—C22—C21	117.34 (18)
O1—C10—H10A	109.5	C21—C22—C17	125.0 (2)
F1—C12—C13—F2	−0.7 (3)	C6—C7—C8—C1	174.40 (18)
F1—C12—C13—C14	176.7 (2)	C6—C7—C8—C9	−1.7 (3)
F2—C13—C14—C15	177.2 (2)	C7—C8—C9—C3	−179.05 (19)
F4—C18—C19—C20	−179.7 (2)	C7—C8—C9—C4	1.2 (3)
O1—C5—C6—C7	−177.85 (18)	C8—C1—C17—C18	−42.9 (3)
N1—C1—C8—C7	165.26 (18)	C8—C1—C17—C22	141.49 (19)
N1—C1—C8—C9	−18.8 (3)	C9—C4—C5—O1	177.43 (18)
N1—C1—C17—C18	82.4 (2)	C9—C4—C5—C6	−2.6 (3)
N1—C1—C17—C22	−93.2 (2)	C10—O1—C5—C4	−11.3 (3)
N1—C2—C3—C9	46.9 (2)	C10—O1—C5—C6	168.75 (18)
N1—C11—C12—F1	−0.5 (3)	C11—N1—C1—C8	−178.28 (17)
N1—C11—C12—C13	175.89 (19)	C11—N1—C1—C17	55.7 (2)
N1—C11—C16—C15	−175.3 (2)	C11—N1—C2—C3	162.49 (17)
C1—N1—C2—C3	−64.5 (2)	C11—C12—C13—F2	−177.24 (19)
C1—N1—C11—C12	83.6 (2)	C11—C12—C13—C14	0.2 (3)
C1—N1—C11—C16	−100.2 (2)	C12—C11—C16—C15	0.9 (3)
C1—C8—C9—C3	5.0 (3)	C12—C13—C14—C15	−0.1 (3)
C1—C8—C9—C4	−174.72 (18)	C13—C14—C15—C16	0.4 (3)
C1—C17—C18—F4	5.2 (3)	C14—C15—C16—C11	−0.8 (4)
C1—C17—C18—C19	−174.0 (2)	C16—C11—C12—F1	−177.0 (2)
C1—C17—C22—F3	−5.1 (3)	C16—C11—C12—C13	−0.5 (3)
C1—C17—C22—C21	174.33 (19)	C17—C1—C8—C7	−69.4 (2)
C2—N1—C1—C8	49.2 (2)	C17—C1—C8—C9	106.6 (2)
C2—N1—C1—C17	−76.8 (2)	C17—C18—C19—C20	−0.5 (3)
C2—N1—C11—C12	−143.8 (2)	C18—C17—C22—F3	178.82 (17)
C2—N1—C11—C16	32.4 (3)	C18—C17—C22—C21	−1.7 (3)
C2—C3—C9—C4	160.66 (19)	C18—C19—C20—C21	−1.1 (3)
C2—C3—C9—C8	−19.1 (3)	C19—C20—C21—C22	1.3 (3)
C4—C5—C6—C7	2.2 (3)	C20—C21—C22—F3	179.66 (18)
C5—C4—C9—C3	−178.86 (19)	C20—C21—C22—C17	0.2 (3)
C5—C4—C9—C8	0.9 (3)	C22—C17—C18—F4	−178.94 (19)
C5—C6—C7—C8	0.0 (3)	C22—C17—C18—C19	1.9 (3)

(6-5)

Crystal data

C22H17F4NO	F(000) = 1600
Mr = 387.36	Dx = 1.459 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9130 reflections
a = 13.3660 (13) Å	θ = 3–27.5°
b = 11.6008 (10) Å	µ = 0.12 mm^−1
c = 30.052 (3) Å	T = 100 K
β = 130.787 (3)°	Irregular, clear light colourless
V = 3528.1 (6) Å^3	0.3 × 0.22 × 0.18 mm
Z = 8

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	5326 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.040
profile data from ω–scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan Blessing 1995	h = −15→15
Tmin = 0.916, Tmax = 1	k = −13→12
18749 measured reflections	l = −35→35
6207 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 1.6536P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
6207 reflections	Δρmax = 0.22 e Å^−3
507 parameters	Δρmin = −0.22 e Å^−3

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
C1	0.21884 (16)	0.07705 (14)	0.29761 (7)	0.0227 (3)
H1	0.3028	0.0364	0.3142	0.027*
C2	0.11783 (16)	0.26892 (15)	0.26249 (7)	0.0262 (4)
H2A	0.138	0.3523	0.2669	0.031*
H2B	0.0722	0.2532	0.2777	0.031*
C3	0.02950 (16)	0.23540 (15)	0.19830 (8)	0.0279 (4)
H3A	−0.0609	0.2643	0.1778	0.033*
H3B	0.0622	0.2732	0.1804	0.033*
C4	−0.06875 (16)	0.06195 (16)	0.13284 (7)	0.0279 (4)
H4	−0.129	0.1125	0.1009	0.033*
C5	−0.07507 (17)	−0.05518 (16)	0.12226 (8)	0.0287 (4)
C6	0.01387 (17)	−0.12973 (15)	0.16847 (8)	0.0274 (4)
H6	0.011	−0.2101	0.1617	0.033*
C7	0.10702 (16)	−0.08490 (15)	0.22470 (7)	0.0254 (4)
H7	0.1677	−0.1357	0.2564	0.03*
C8	0.11375 (16)	0.03283 (14)	0.23579 (7)	0.0232 (4)
C9	0.02356 (16)	0.10702 (15)	0.18895 (7)	0.0244 (4)
C10	−0.1757 (2)	−0.20627 (19)	0.05167 (9)	0.0455 (5)
H10A	−0.2421	−0.2176	0.009	0.068*
H10B	−0.1986	−0.2533	0.071	0.068*
H10C	−0.0887	−0.2294	0.0657	0.068*
C11	0.35025 (16)	0.24874 (14)	0.35101 (7)	0.0245 (4)
C12	0.47736 (17)	0.21130 (15)	0.37719 (8)	0.0272 (4)
C13	0.58695 (17)	0.25280 (17)	0.43072 (8)	0.0324 (4)
C14	0.57649 (19)	0.33494 (18)	0.46041 (8)	0.0385 (5)
H14	0.6526	0.3636	0.4973	0.046*
C15	0.4512 (2)	0.37470 (18)	0.43475 (8)	0.0382 (5)
H15	0.4416	0.4321	0.4543	0.046*
C16	0.33991 (18)	0.33239 (16)	0.38122 (8)	0.0301 (4)
H16	0.2552	0.3607	0.3648	0.036*
C17	0.18909 (16)	0.04897 (14)	0.33770 (7)	0.0223 (3)
C18	0.29373 (16)	0.02309 (14)	0.39653 (7)	0.0239 (4)
H18	0.382	0.0244	0.4114	0.029*
C19	0.26872 (17)	−0.00433 (15)	0.43298 (7)	0.0268 (4)
C20	0.14135 (18)	−0.00512 (15)	0.41251 (8)	0.0278 (4)
C21	0.03692 (17)	0.02178 (15)	0.35494 (8)	0.0277 (4)
H21	−0.0507	0.0226	0.3409	0.033*
C22	0.06079 (16)	0.04774 (14)	0.31751 (7)	0.0246 (4)
H22	−0.0114	0.065	0.2775	0.03*
N1	0.24120 (13)	0.20196 (12)	0.29603 (6)	0.0235 (3)
O1	−0.17243 (12)	−0.08812 (12)	0.06508 (5)	0.0367 (3)
F4	0.12230 (11)	−0.03170 (10)	0.44999 (5)	0.0408 (3)
F3	0.36983 (10)	−0.03215 (9)	0.48984 (4)	0.0358 (3)
F1	0.49554 (10)	0.13345 (9)	0.34939 (5)	0.0347 (3)
F2	0.70710 (10)	0.21302 (10)	0.45308 (5)	0.0439 (3)
C23	0.37651 (16)	0.53834 (13)	0.26440 (7)	0.0217 (3)
H23	0.3418	0.498	0.2813	0.026*
C24	0.36799 (17)	0.72893 (14)	0.22633 (7)	0.0259 (4)
H24A	0.4592	0.7156	0.2421	0.031*
H24B	0.3572	0.8123	0.2291	0.031*
C25	0.26941 (17)	0.69040 (14)	0.16267 (7)	0.0264 (4)
H25A	0.1823	0.7249	0.1442	0.032*
H25B	0.298	0.7201	0.1416	0.032*
C26	0.18376 (16)	0.51224 (14)	0.10004 (7)	0.0250 (4)
H26	0.152	0.56	0.0675	0.03*
C27	0.15904 (16)	0.39509 (15)	0.09158 (7)	0.0252 (4)
C28	0.20782 (16)	0.32379 (14)	0.13909 (7)	0.0256 (4)
H28	0.192	0.2431	0.1337	0.031*
C29	0.27999 (15)	0.37237 (14)	0.19454 (7)	0.0235 (3)
H29	0.3144	0.3238	0.2272	0.028*
C30	0.30317 (15)	0.49035 (14)	0.20344 (7)	0.0215 (3)
C31	0.25406 (16)	0.56104 (14)	0.15520 (7)	0.0232 (3)
C32	0.0378 (2)	0.24149 (16)	0.02274 (8)	0.0373 (4)
H32A	−0.0267	0.2293	−0.0199	0.056*
H32B	−0.0042	0.227	0.0394	0.056*
H32C	0.1123	0.1885	0.0404	0.056*
C33	0.39700 (16)	0.71268 (14)	0.31486 (7)	0.0245 (4)
C34	0.34683 (16)	0.67661 (15)	0.34112 (7)	0.0271 (4)
C35	0.39475 (17)	0.72025 (17)	0.39438 (8)	0.0311 (4)
C36	0.49246 (18)	0.80268 (16)	0.42378 (8)	0.0333 (4)
H36	0.525	0.8319	0.4607	0.04*
C37	0.54161 (18)	0.84145 (16)	0.39790 (8)	0.0325 (4)
H37	0.608	0.8994	0.4169	0.039*
C38	0.49561 (17)	0.79715 (15)	0.34458 (8)	0.0279 (4)
H38	0.5317	0.8247	0.3279	0.033*
C39	0.52510 (16)	0.51766 (13)	0.30627 (7)	0.0209 (3)
C40	0.59111 (16)	0.49473 (14)	0.36511 (7)	0.0242 (4)
H40	0.5428	0.4882	0.378	0.029*
C41	0.72664 (16)	0.48140 (14)	0.40470 (7)	0.0244 (4)
C42	0.79816 (16)	0.49020 (14)	0.38643 (8)	0.0248 (4)
C43	0.73610 (16)	0.51379 (14)	0.32911 (7)	0.0241 (4)
H43	0.7857	0.5215	0.3169	0.029*
C44	0.59888 (16)	0.52649 (13)	0.28866 (7)	0.0220 (3)
H44	0.5552	0.5414	0.2486	0.026*
N2	0.34520 (13)	0.66325 (11)	0.26058 (6)	0.0231 (3)
O2	0.08430 (12)	0.35726 (10)	0.03476 (5)	0.0320 (3)
F7	0.79186 (10)	0.46026 (10)	0.46179 (4)	0.0358 (3)
F8	0.93073 (9)	0.47588 (9)	0.42659 (4)	0.0326 (2)
F5	0.24758 (10)	0.59821 (10)	0.31391 (4)	0.0346 (3)
F6	0.34051 (11)	0.68169 (11)	0.41684 (5)	0.0459 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0193 (8)	0.0233 (8)	0.0267 (9)	0.0023 (6)	0.0154 (7)	0.0023 (7)
C2	0.0234 (8)	0.0238 (9)	0.0304 (9)	0.0034 (7)	0.0171 (8)	0.0031 (7)
C3	0.0213 (8)	0.0281 (9)	0.0287 (9)	0.0029 (7)	0.0139 (8)	0.0045 (7)
C4	0.0212 (9)	0.0353 (10)	0.0260 (9)	−0.0005 (7)	0.0150 (8)	0.0033 (7)
C5	0.0228 (9)	0.0407 (11)	0.0253 (9)	−0.0093 (8)	0.0170 (8)	−0.0055 (8)
C6	0.0304 (9)	0.0262 (9)	0.0353 (10)	−0.0061 (7)	0.0257 (9)	−0.0045 (7)
C7	0.0247 (9)	0.0272 (9)	0.0293 (9)	−0.0005 (7)	0.0198 (8)	0.0018 (7)
C8	0.0198 (8)	0.0288 (9)	0.0252 (9)	−0.0013 (7)	0.0165 (8)	−0.0004 (7)
C9	0.0184 (8)	0.0296 (9)	0.0267 (9)	−0.0004 (7)	0.0154 (8)	0.0008 (7)
C10	0.0391 (11)	0.0521 (13)	0.0397 (12)	−0.0142 (10)	0.0233 (10)	−0.0193 (10)
C11	0.0253 (9)	0.0255 (9)	0.0250 (9)	−0.0035 (7)	0.0174 (8)	0.0016 (7)
C12	0.0276 (9)	0.0278 (9)	0.0296 (9)	−0.0029 (7)	0.0201 (8)	0.0014 (7)
C13	0.0236 (9)	0.0414 (11)	0.0287 (10)	−0.0032 (8)	0.0155 (8)	0.0075 (8)
C14	0.0348 (11)	0.0539 (13)	0.0238 (9)	−0.0144 (9)	0.0178 (9)	−0.0022 (9)
C15	0.0433 (11)	0.0475 (12)	0.0325 (10)	−0.0135 (9)	0.0286 (10)	−0.0110 (9)
C16	0.0302 (10)	0.0363 (10)	0.0305 (9)	−0.0044 (8)	0.0227 (9)	−0.0022 (8)
C17	0.0208 (8)	0.0203 (8)	0.0234 (8)	0.0007 (6)	0.0134 (7)	0.0001 (6)
C18	0.0198 (8)	0.0238 (9)	0.0272 (9)	−0.0009 (6)	0.0150 (8)	−0.0006 (7)
C19	0.0229 (9)	0.0266 (9)	0.0225 (9)	−0.0003 (7)	0.0112 (8)	0.0018 (7)
C20	0.0309 (9)	0.0299 (9)	0.0301 (9)	−0.0040 (7)	0.0232 (9)	−0.0021 (7)
C21	0.0221 (9)	0.0297 (9)	0.0326 (10)	−0.0009 (7)	0.0184 (8)	−0.0016 (7)
C22	0.0193 (8)	0.0253 (9)	0.0246 (9)	−0.0003 (7)	0.0123 (7)	−0.0001 (7)
N1	0.0202 (7)	0.0226 (7)	0.0250 (7)	0.0000 (6)	0.0136 (6)	0.0003 (6)
O1	0.0322 (7)	0.0447 (8)	0.0274 (7)	−0.0126 (6)	0.0169 (6)	−0.0088 (6)
F4	0.0374 (6)	0.0591 (7)	0.0360 (6)	−0.0029 (5)	0.0285 (6)	0.0049 (5)
F3	0.0262 (5)	0.0482 (7)	0.0235 (5)	−0.0006 (5)	0.0121 (5)	0.0073 (5)
F1	0.0252 (5)	0.0351 (6)	0.0439 (6)	0.0000 (4)	0.0227 (5)	−0.0039 (5)
F2	0.0216 (5)	0.0547 (7)	0.0406 (6)	−0.0012 (5)	0.0139 (5)	0.0065 (5)
C23	0.0217 (8)	0.0199 (8)	0.0261 (9)	0.0010 (6)	0.0167 (8)	0.0033 (7)
C24	0.0282 (9)	0.0209 (8)	0.0327 (10)	0.0012 (7)	0.0217 (8)	0.0037 (7)
C25	0.0301 (9)	0.0223 (9)	0.0290 (9)	0.0038 (7)	0.0204 (8)	0.0063 (7)
C26	0.0241 (9)	0.0259 (9)	0.0261 (9)	0.0033 (7)	0.0169 (8)	0.0059 (7)
C27	0.0205 (8)	0.0280 (9)	0.0245 (9)	0.0018 (7)	0.0136 (8)	0.0011 (7)
C28	0.0226 (9)	0.0207 (8)	0.0307 (9)	0.0016 (7)	0.0162 (8)	0.0022 (7)
C29	0.0194 (8)	0.0236 (9)	0.0252 (9)	0.0017 (6)	0.0136 (7)	0.0050 (7)
C30	0.0151 (8)	0.0240 (8)	0.0242 (9)	0.0010 (6)	0.0122 (7)	0.0023 (7)
C31	0.0198 (8)	0.0236 (9)	0.0280 (9)	0.0021 (7)	0.0164 (8)	0.0031 (7)
C32	0.0393 (11)	0.0311 (10)	0.0285 (10)	−0.0033 (8)	0.0165 (9)	−0.0038 (8)
C33	0.0217 (8)	0.0233 (9)	0.0272 (9)	0.0067 (7)	0.0154 (8)	0.0031 (7)
C34	0.0177 (8)	0.0320 (10)	0.0275 (9)	0.0007 (7)	0.0130 (8)	−0.0004 (7)
C35	0.0257 (9)	0.0418 (11)	0.0293 (9)	0.0042 (8)	0.0196 (8)	0.0019 (8)
C36	0.0294 (10)	0.0371 (10)	0.0278 (9)	0.0067 (8)	0.0162 (8)	−0.0028 (8)
C37	0.0289 (10)	0.0264 (10)	0.0359 (10)	0.0010 (7)	0.0184 (9)	−0.0043 (8)
C38	0.0262 (9)	0.0243 (9)	0.0342 (10)	0.0022 (7)	0.0203 (8)	0.0006 (7)
C39	0.0214 (8)	0.0155 (8)	0.0238 (8)	0.0002 (6)	0.0138 (7)	−0.0004 (6)
C40	0.0240 (9)	0.0241 (9)	0.0273 (9)	0.0011 (7)	0.0179 (8)	0.0028 (7)
C41	0.0247 (9)	0.0224 (9)	0.0220 (8)	0.0009 (7)	0.0134 (8)	0.0025 (7)
C42	0.0177 (8)	0.0212 (8)	0.0292 (9)	0.0002 (6)	0.0126 (8)	−0.0028 (7)
C43	0.0251 (9)	0.0208 (8)	0.0314 (9)	−0.0033 (7)	0.0206 (8)	−0.0047 (7)
C44	0.0232 (8)	0.0183 (8)	0.0252 (8)	−0.0006 (6)	0.0162 (7)	−0.0008 (6)
N2	0.0248 (7)	0.0208 (7)	0.0266 (7)	0.0023 (6)	0.0180 (7)	0.0021 (6)
O2	0.0354 (7)	0.0273 (7)	0.0244 (6)	−0.0004 (5)	0.0156 (6)	0.0003 (5)
F7	0.0270 (5)	0.0494 (7)	0.0246 (5)	0.0028 (5)	0.0141 (5)	0.0071 (5)
F8	0.0184 (5)	0.0383 (6)	0.0324 (6)	0.0026 (4)	0.0128 (5)	0.0016 (4)
F5	0.0259 (5)	0.0494 (7)	0.0306 (6)	−0.0098 (5)	0.0193 (5)	−0.0054 (5)
F6	0.0398 (7)	0.0733 (9)	0.0347 (6)	−0.0092 (6)	0.0287 (6)	−0.0067 (6)

Geometric parameters (Å, º)

C1—H1	1	C23—H23	1
C1—C8	1.509 (2)	C23—C30	1.510 (2)
C1—C17	1.530 (2)	C23—C39	1.523 (2)
C1—N1	1.487 (2)	C23—N2	1.492 (2)
C2—H2A	0.99	C24—H24A	0.99
C2—H2B	0.99	C24—H24B	0.99
C2—C3	1.514 (2)	C24—C25	1.517 (2)
C2—N1	1.472 (2)	C24—N2	1.464 (2)
C3—H3A	0.99	C25—H25A	0.99
C3—H3B	0.99	C25—H25B	0.99
C3—C9	1.508 (2)	C25—C31	1.511 (2)
C4—H4	0.95	C26—H26	0.95
C4—C5	1.385 (3)	C26—C27	1.382 (2)
C4—C9	1.386 (2)	C26—C31	1.384 (2)
C5—C6	1.390 (3)	C27—C28	1.390 (2)
C5—O1	1.368 (2)	C27—O2	1.370 (2)
C6—H6	0.95	C28—H28	0.95
C6—C7	1.388 (2)	C28—C29	1.387 (2)
C7—H7	0.95	C29—H29	0.95
C7—C8	1.395 (2)	C29—C30	1.390 (2)
C8—C9	1.399 (2)	C30—C31	1.401 (2)
C10—H10A	0.98	C32—H32A	0.98
C10—H10B	0.98	C32—H32B	0.98
C10—H10C	0.98	C32—H32C	0.98
C10—O1	1.421 (2)	C32—O2	1.424 (2)
C11—C12	1.396 (2)	C33—C34	1.392 (2)
C11—C16	1.396 (2)	C33—C38	1.399 (2)
C11—N1	1.415 (2)	C33—N2	1.412 (2)
C12—C13	1.374 (3)	C34—C35	1.374 (2)
C12—F1	1.356 (2)	C34—F5	1.356 (2)
C13—C14	1.374 (3)	C35—C36	1.376 (3)
C13—F2	1.354 (2)	C35—F6	1.349 (2)
C14—H14	0.95	C36—H36	0.95
C14—C15	1.388 (3)	C36—C37	1.380 (3)
C15—H15	0.95	C37—H37	0.95
C15—C16	1.384 (3)	C37—C38	1.387 (3)
C16—H16	0.95	C38—H38	0.95
C17—C18	1.393 (2)	C39—C40	1.392 (2)
C17—C22	1.396 (2)	C39—C44	1.395 (2)
C18—H18	0.95	C40—H40	0.95
C18—C19	1.375 (2)	C40—C41	1.380 (2)
C19—C20	1.382 (2)	C41—C42	1.382 (2)
C19—F3	1.3542 (19)	C41—F7	1.3451 (19)
C20—C21	1.372 (3)	C42—C43	1.365 (2)
C20—F4	1.3428 (19)	C42—F8	1.3528 (19)
C21—H21	0.95	C43—H43	0.95
C21—C22	1.388 (2)	C43—C44	1.397 (2)
C22—H22	0.95	C44—H44	0.95
C8—C1—H1	107	C30—C23—H23	107.1
C8—C1—C17	112.66 (13)	C30—C23—C39	114.01 (13)
C17—C1—H1	107	C39—C23—H23	107.1
N1—C1—H1	107	N2—C23—H23	107.1
N1—C1—C8	109.68 (13)	N2—C23—C30	109.73 (13)
N1—C1—C17	113.19 (13)	N2—C23—C39	111.43 (13)
H2A—C2—H2B	108.3	H24A—C24—H24B	108.3
C3—C2—H2A	109.8	C25—C24—H24A	109.9
C3—C2—H2B	109.8	C25—C24—H24B	109.9
N1—C2—H2A	109.8	N2—C24—H24A	109.9
N1—C2—H2B	109.8	N2—C24—H24B	109.9
N1—C2—C3	109.23 (13)	N2—C24—C25	108.97 (13)
C2—C3—H3A	108.9	C24—C25—H25A	108.8
C2—C3—H3B	108.9	C24—C25—H25B	108.8
H3A—C3—H3B	107.8	H25A—C25—H25B	107.7
C9—C3—C2	113.17 (14)	C31—C25—C24	113.67 (14)
C9—C3—H3A	108.9	C31—C25—H25A	108.8
C9—C3—H3B	108.9	C31—C25—H25B	108.8
C5—C4—H4	119.3	C27—C26—H26	119.5
C5—C4—C9	121.44 (16)	C27—C26—C31	121.05 (15)
C9—C4—H4	119.3	C31—C26—H26	119.5
C4—C5—C6	119.78 (16)	C26—C27—C28	120.06 (16)
O1—C5—C4	115.32 (16)	O2—C27—C26	115.85 (14)
O1—C5—C6	124.89 (17)	O2—C27—C28	124.09 (15)
C5—C6—H6	120.5	C27—C28—H28	120.5
C7—C6—C5	118.98 (16)	C29—C28—C27	118.92 (16)
C7—C6—H6	120.5	C29—C28—H28	120.5
C6—C7—H7	119.2	C28—C29—H29	119.2
C6—C7—C8	121.61 (16)	C28—C29—C30	121.59 (15)
C8—C7—H7	119.2	C30—C29—H29	119.2
C7—C8—C1	119.33 (15)	C29—C30—C23	118.88 (14)
C7—C8—C9	118.89 (15)	C29—C30—C31	118.84 (15)
C9—C8—C1	121.78 (15)	C31—C30—C23	122.25 (15)
C4—C9—C3	119.73 (15)	C26—C31—C25	120.26 (15)
C4—C9—C8	119.28 (16)	C26—C31—C30	119.51 (15)
C8—C9—C3	120.93 (15)	C30—C31—C25	120.09 (15)
H10A—C10—H10B	109.5	H32A—C32—H32B	109.5
H10A—C10—H10C	109.5	H32A—C32—H32C	109.5
H10B—C10—H10C	109.5	H32B—C32—H32C	109.5
O1—C10—H10A	109.5	O2—C32—H32A	109.5
O1—C10—H10B	109.5	O2—C32—H32B	109.5
O1—C10—H10C	109.5	O2—C32—H32C	109.5
C12—C11—C16	116.80 (16)	C34—C33—C38	116.77 (16)
C12—C11—N1	119.01 (15)	C34—C33—N2	118.59 (15)
C16—C11—N1	124.18 (15)	C38—C33—N2	124.65 (15)
C13—C12—C11	121.69 (17)	C35—C34—C33	121.25 (16)
F1—C12—C11	120.14 (15)	F5—C34—C33	120.23 (15)
F1—C12—C13	118.16 (15)	F5—C34—C35	118.51 (15)
C12—C13—C14	121.38 (17)	C34—C35—C36	121.90 (16)
F2—C13—C12	118.25 (17)	F6—C35—C34	117.81 (16)
F2—C13—C14	120.34 (17)	F6—C35—C36	120.27 (16)
C13—C14—H14	121.1	C35—C36—H36	121.1
C13—C14—C15	117.89 (17)	C35—C36—C37	117.78 (17)
C15—C14—H14	121.1	C37—C36—H36	121.1
C14—C15—H15	119.4	C36—C37—H37	119.5
C16—C15—C14	121.24 (18)	C36—C37—C38	121.02 (17)
C16—C15—H15	119.4	C38—C37—H37	119.5
C11—C16—H16	119.5	C33—C38—H38	119.4
C15—C16—C11	120.98 (17)	C37—C38—C33	121.26 (16)
C15—C16—H16	119.5	C37—C38—H38	119.4
C18—C17—C1	118.90 (14)	C40—C39—C23	118.81 (14)
C18—C17—C22	118.62 (15)	C40—C39—C44	118.52 (15)
C22—C17—C1	122.49 (14)	C44—C39—C23	122.59 (14)
C17—C18—H18	120.1	C39—C40—H40	119.9
C19—C18—C17	119.72 (15)	C41—C40—C39	120.16 (15)
C19—C18—H18	120.1	C41—C40—H40	119.9
C18—C19—C20	121.13 (16)	C40—C41—C42	120.53 (15)
F3—C19—C18	119.93 (15)	F7—C41—C40	120.80 (15)
F3—C19—C20	118.95 (15)	F7—C41—C42	118.67 (15)
C21—C20—C19	120.17 (16)	C43—C42—C41	120.54 (15)
F4—C20—C19	118.80 (16)	F8—C42—C41	118.63 (15)
F4—C20—C21	121.03 (15)	F8—C42—C43	120.83 (15)
C20—C21—H21	120.4	C42—C43—H43	120.3
C20—C21—C22	119.20 (16)	C42—C43—C44	119.31 (15)
C22—C21—H21	120.4	C44—C43—H43	120.3
C17—C22—H22	119.4	C39—C44—C43	120.93 (15)
C21—C22—C17	121.15 (16)	C39—C44—H44	119.5
C21—C22—H22	119.4	C43—C44—H44	119.5
C2—N1—C1	112.18 (12)	C24—N2—C23	112.51 (12)
C11—N1—C1	114.32 (13)	C33—N2—C23	113.86 (13)
C11—N1—C2	115.84 (13)	C33—N2—C24	115.51 (14)
C5—O1—C10	116.97 (15)	C27—O2—C32	117.41 (13)
C1—C8—C9—C3	1.1 (2)	C23—C30—C31—C25	−2.2 (2)
C1—C8—C9—C4	178.40 (14)	C23—C30—C31—C26	−177.83 (14)
C1—C17—C18—C19	−178.87 (15)	C23—C39—C40—C41	−176.72 (15)
C1—C17—C22—C21	179.91 (16)	C23—C39—C44—C43	176.08 (14)
C2—C3—C9—C4	169.80 (14)	C24—C25—C31—C26	−169.97 (14)
C2—C3—C9—C8	−13.0 (2)	C24—C25—C31—C30	14.4 (2)
C3—C2—N1—C1	−67.13 (17)	C25—C24—N2—C23	66.76 (17)
C3—C2—N1—C11	159.11 (14)	C25—C24—N2—C33	−160.16 (13)
C4—C5—C6—C7	0.6 (2)	C26—C27—C28—C29	0.6 (2)
C4—C5—O1—C10	175.32 (15)	C26—C27—O2—C32	−169.50 (15)
C5—C4—C9—C3	178.34 (15)	C27—C26—C31—C25	−174.40 (15)
C5—C4—C9—C8	1.1 (2)	C27—C26—C31—C30	1.3 (2)
C5—C6—C7—C8	−0.3 (2)	C27—C28—C29—C30	0.7 (2)
C6—C5—O1—C10	−4.9 (2)	C28—C27—O2—C32	9.7 (2)
C6—C7—C8—C1	−178.78 (14)	C28—C29—C30—C23	176.91 (14)
C6—C7—C8—C9	0.4 (2)	C28—C29—C30—C31	−1.1 (2)
C7—C8—C9—C3	−178.03 (14)	C29—C30—C31—C25	175.77 (14)
C7—C8—C9—C4	−0.8 (2)	C29—C30—C31—C26	0.1 (2)
C8—C1—C17—C18	144.54 (15)	C30—C23—C39—C40	−143.68 (15)
C8—C1—C17—C22	−35.2 (2)	C30—C23—C39—C44	39.6 (2)
C8—C1—N1—C2	53.70 (16)	C30—C23—N2—C24	−53.10 (17)
C8—C1—N1—C11	−171.81 (13)	C30—C23—N2—C33	173.02 (13)
C9—C4—C5—C6	−0.9 (2)	C31—C26—C27—C28	−1.6 (2)
C9—C4—C5—O1	178.81 (14)	C31—C26—C27—O2	177.63 (14)
C11—C12—C13—C14	−1.3 (3)	C33—C34—C35—C36	1.1 (3)
C11—C12—C13—F2	−179.46 (15)	C33—C34—C35—F6	179.54 (15)
C12—C11—C16—C15	−0.5 (2)	C34—C33—C38—C37	0.7 (2)
C12—C11—N1—C1	65.93 (19)	C34—C33—N2—C23	−66.97 (18)
C12—C11—N1—C2	−161.29 (14)	C34—C33—N2—C24	160.58 (15)
C12—C13—C14—C15	0.3 (3)	C34—C35—C36—C37	0.3 (3)
C13—C14—C15—C16	0.6 (3)	C35—C36—C37—C38	−1.2 (3)
C14—C15—C16—C11	−0.5 (3)	C36—C37—C38—C33	0.7 (3)
C16—C11—C12—C13	1.4 (2)	C38—C33—C34—C35	−1.6 (2)
C16—C11—C12—F1	−177.51 (14)	C38—C33—C34—F5	177.50 (14)
C16—C11—N1—C1	−114.95 (17)	C38—C33—N2—C23	113.62 (17)
C16—C11—N1—C2	17.8 (2)	C38—C33—N2—C24	−18.8 (2)
C17—C1—C8—C7	−74.25 (18)	C39—C23—C30—C29	76.55 (18)
C17—C1—C8—C9	106.58 (17)	C39—C23—C30—C31	−105.52 (17)
C17—C1—N1—C2	−73.04 (17)	C39—C23—N2—C24	74.14 (16)
C17—C1—N1—C11	61.44 (17)	C39—C23—N2—C33	−59.74 (17)
C17—C18—C19—C20	−0.9 (3)	C39—C40—C41—C42	−0.2 (2)
C17—C18—C19—F3	178.47 (15)	C39—C40—C41—F7	179.39 (15)
C18—C17—C22—C21	0.2 (2)	C40—C39—C44—C43	−0.6 (2)
C18—C19—C20—C21	0.0 (3)	C40—C41—C42—C43	0.9 (2)
C18—C19—C20—F4	−179.53 (16)	C40—C41—C42—F8	−179.61 (14)
C19—C20—C21—C22	1.1 (3)	C41—C42—C43—C44	−1.4 (2)
C20—C21—C22—C17	−1.2 (3)	C42—C43—C44—C39	1.3 (2)
C22—C17—C18—C19	0.8 (2)	C44—C39—C40—C41	0.1 (2)
N1—C1—C8—C7	158.70 (13)	N2—C23—C30—C29	−157.67 (14)
N1—C1—C8—C9	−20.46 (19)	N2—C23—C30—C31	20.3 (2)
N1—C1—C17—C18	−90.30 (17)	N2—C23—C39—C40	91.44 (17)
N1—C1—C17—C22	90.01 (18)	N2—C23—C39—C44	−85.25 (18)
N1—C2—C3—C9	44.03 (18)	N2—C24—C25—C31	−44.91 (18)
N1—C11—C12—C13	−179.44 (15)	N2—C33—C34—C35	178.97 (15)
N1—C11—C12—F1	1.7 (2)	N2—C33—C34—F5	−2.0 (2)
N1—C11—C16—C15	−179.61 (16)	N2—C33—C38—C37	−179.90 (15)
O1—C5—C6—C7	−179.18 (15)	O2—C27—C28—C29	−178.57 (15)
F4—C20—C21—C22	−179.42 (16)	F7—C41—C42—C43	−178.73 (15)
F3—C19—C20—C21	−179.45 (16)	F7—C41—C42—F8	0.7 (2)
F3—C19—C20—F4	1.0 (2)	F8—C42—C43—C44	179.13 (14)
F1—C12—C13—C14	177.59 (16)	F5—C34—C35—C36	−177.95 (16)
F1—C12—C13—F2	−0.6 (2)	F5—C34—C35—F6	0.4 (2)
F2—C13—C14—C15	178.40 (16)	F6—C35—C36—C37	−178.10 (16)

(6-6)

Crystal data

C22H17F4NO	F(000) = 1600
Mr = 387.36	Dx = 1.46 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4165 reflections
a = 22.323 (8) Å	θ = 3–27.4°
b = 13.499 (5) Å	µ = 0.12 mm^−1
c = 11.828 (5) Å	T = 100 K
β = 98.459 (17)°	Needle, clear light colourless
V = 3526 (2) Å^3	0.2 × 0.2 × 0.1 mm
Z = 8

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2301 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.077
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Blessing 1995	h = −28→28
Tmin = 0.713, Tmax = 1	k = −17→17
10335 measured reflections	l = −15→13
4010 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0481P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
4010 reflections	Δρmax = 0.28 e Å^−3
254 parameters	Δρmin = −0.32 e Å^−3

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
F1	0.57206 (6)	0.27905 (11)	0.35110 (10)	0.0487 (4)
F2	0.56593 (6)	0.08251 (11)	0.33378 (12)	0.0597 (4)
F3	0.78495 (6)	0.16624 (12)	0.67940 (10)	0.0537 (4)
F4	0.80789 (5)	0.49115 (11)	0.82131 (11)	0.0547 (4)
O1	0.62123 (6)	0.83390 (12)	0.46662 (13)	0.0411 (4)
N1	0.57938 (7)	0.37686 (15)	0.55817 (13)	0.0336 (4)
C1	0.63623 (8)	0.41640 (17)	0.52456 (16)	0.0322 (5)
H1	0.6401	0.3872	0.4483	0.039*
C2	0.56389 (9)	0.42765 (18)	0.66019 (16)	0.0378 (6)
H2A	0.5985	0.4235	0.7228	0.045*
H2B	0.5287	0.3946	0.686	0.045*
C3	0.54879 (9)	0.53591 (18)	0.63334 (17)	0.0357 (6)
H3A	0.5067	0.5404	0.5935	0.043*
H3B	0.551	0.573	0.706	0.043*
C4	0.58813 (8)	0.68581 (18)	0.54228 (16)	0.0354 (6)
H4	0.5597	0.7243	0.5756	0.042*
C5	0.62674 (9)	0.73243 (19)	0.47644 (17)	0.0356 (5)
C6	0.66779 (9)	0.67609 (19)	0.42611 (16)	0.0358 (6)
H6	0.6943	0.7068	0.3809	0.043*
C7	0.66939 (9)	0.57458 (19)	0.44291 (16)	0.0361 (6)
H7	0.6976	0.5362	0.4087	0.043*
C8	0.63099 (8)	0.52670 (18)	0.50841 (16)	0.0313 (5)
C9	0.59056 (8)	0.58428 (18)	0.56003 (16)	0.0319 (5)
C10	0.66642 (10)	0.8848 (2)	0.41514 (19)	0.0454 (6)
H10A	0.6633	0.8655	0.3346	0.068*
H10B	0.7067	0.8673	0.4551	0.068*
H10C	0.6603	0.9564	0.4204	0.068*
C11	0.57253 (8)	0.27336 (18)	0.55267 (18)	0.0349 (5)
C12	0.57032 (9)	0.22502 (19)	0.44788 (18)	0.0391 (6)
C13	0.56650 (10)	0.1236 (2)	0.4390 (2)	0.0455 (6)
C14	0.56326 (9)	0.0645 (2)	0.5321 (2)	0.0506 (7)
H14	0.5618	−0.0056	0.5255	0.061*
C15	0.56222 (10)	0.1112 (2)	0.6368 (2)	0.0497 (7)
H15	0.5579	0.0724	0.7021	0.06*
C16	0.56729 (9)	0.2126 (2)	0.64755 (19)	0.0417 (6)
H16	0.5673	0.2422	0.7204	0.05*
C17	0.69308 (8)	0.38555 (19)	0.60696 (16)	0.0349 (6)
C18	0.72549 (8)	0.4542 (2)	0.68005 (17)	0.0375 (6)
H18	0.7124	0.5211	0.6813	0.045*
C19	0.77678 (9)	0.4232 (2)	0.75037 (17)	0.0420 (6)
C20	0.79861 (10)	0.3276 (2)	0.75261 (18)	0.0463 (7)
H20	0.8345	0.3085	0.8011	0.056*
C21	0.76531 (9)	0.2618 (2)	0.68036 (18)	0.0421 (6)
C22	0.71334 (9)	0.28752 (19)	0.60739 (17)	0.0380 (6)
H22	0.6919	0.2395	0.5585	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0487 (8)	0.0681 (10)	0.0276 (7)	0.0176 (7)	0.0004 (5)	−0.0034 (6)
F2	0.0484 (8)	0.0712 (11)	0.0566 (10)	0.0067 (8)	−0.0020 (7)	−0.0208 (8)
F3	0.0426 (7)	0.0809 (12)	0.0388 (8)	0.0299 (8)	0.0102 (6)	0.0160 (7)
F4	0.0326 (7)	0.0939 (13)	0.0341 (8)	−0.0048 (7)	−0.0071 (6)	0.0075 (7)
O1	0.0298 (8)	0.0524 (11)	0.0416 (9)	0.0025 (8)	0.0070 (6)	−0.0038 (8)
N1	0.0253 (9)	0.0546 (13)	0.0215 (9)	0.0090 (9)	0.0053 (7)	−0.0008 (8)
C1	0.0230 (10)	0.0569 (16)	0.0171 (10)	0.0081 (10)	0.0045 (7)	0.0010 (9)
C2	0.0256 (10)	0.0665 (18)	0.0224 (11)	0.0060 (11)	0.0070 (8)	−0.0026 (10)
C3	0.0232 (10)	0.0617 (17)	0.0226 (11)	0.0027 (11)	0.0047 (8)	−0.0085 (10)
C4	0.0202 (9)	0.0586 (17)	0.0264 (11)	0.0050 (11)	0.0007 (8)	−0.0100 (10)
C5	0.0252 (10)	0.0536 (17)	0.0262 (11)	0.0043 (11)	−0.0025 (8)	−0.0047 (10)
C6	0.0255 (10)	0.0609 (17)	0.0207 (11)	0.0055 (11)	0.0023 (8)	0.0030 (10)
C7	0.0261 (10)	0.0622 (17)	0.0201 (10)	0.0091 (11)	0.0040 (8)	−0.0014 (10)
C8	0.0215 (9)	0.0550 (16)	0.0164 (10)	0.0072 (10)	−0.0005 (7)	−0.0026 (9)
C9	0.0208 (9)	0.0536 (15)	0.0203 (10)	0.0050 (10)	−0.0006 (7)	−0.0045 (10)
C10	0.0352 (12)	0.0632 (18)	0.0375 (13)	0.0003 (12)	0.0042 (10)	0.0041 (12)
C11	0.0188 (10)	0.0536 (16)	0.0317 (12)	0.0046 (11)	0.0013 (8)	0.0002 (10)
C12	0.0267 (11)	0.0594 (17)	0.0300 (12)	0.0078 (12)	0.0002 (8)	0.0007 (11)
C13	0.0271 (11)	0.0632 (18)	0.0437 (15)	0.0038 (13)	−0.0029 (10)	−0.0125 (13)
C14	0.0289 (12)	0.0599 (18)	0.0613 (18)	−0.0085 (13)	0.0015 (11)	−0.0010 (14)
C15	0.0300 (12)	0.065 (2)	0.0533 (16)	−0.0114 (13)	0.0045 (11)	0.0116 (14)
C16	0.0238 (10)	0.0645 (19)	0.0362 (13)	−0.0043 (12)	0.0024 (9)	0.0007 (12)
C17	0.0208 (9)	0.0666 (17)	0.0183 (10)	0.0097 (11)	0.0059 (8)	0.0079 (10)
C18	0.0238 (10)	0.0669 (17)	0.0231 (11)	0.0056 (11)	0.0076 (8)	0.0066 (10)
C19	0.0245 (10)	0.079 (2)	0.0218 (11)	−0.0016 (12)	0.0011 (8)	0.0088 (11)
C20	0.0247 (10)	0.088 (2)	0.0260 (12)	0.0115 (13)	0.0046 (9)	0.0172 (12)
C21	0.0310 (12)	0.0699 (19)	0.0275 (12)	0.0187 (12)	0.0115 (9)	0.0136 (11)
C22	0.0267 (10)	0.0640 (17)	0.0245 (11)	0.0124 (12)	0.0085 (8)	0.0051 (11)

Geometric parameters (Å, º)

F1—C12	1.363 (3)	C7—H7	0.95
F2—C13	1.361 (3)	C7—C8	1.396 (3)
F3—C21	1.363 (3)	C8—C9	1.398 (3)
F4—C19	1.363 (3)	C10—H10A	0.98
O1—C5	1.379 (3)	C10—H10B	0.98
O1—C10	1.429 (2)	C10—H10C	0.98
N1—C1	1.484 (2)	C11—C12	1.395 (3)
N1—C2	1.473 (2)	C11—C16	1.408 (3)
N1—C11	1.406 (3)	C12—C13	1.375 (4)
C1—H1	1	C13—C14	1.371 (4)
C1—C8	1.504 (3)	C14—H14	0.95
C1—C17	1.540 (3)	C14—C15	1.392 (3)
C2—H2A	0.99	C15—H15	0.95
C2—H2B	0.99	C15—C16	1.378 (3)
C2—C3	1.523 (3)	C16—H16	0.95
C3—H3A	0.99	C17—C18	1.395 (3)
C3—H3B	0.99	C17—C22	1.398 (3)
C3—C9	1.512 (3)	C18—H18	0.95
C4—H4	0.95	C18—C19	1.378 (3)
C4—C5	1.394 (3)	C19—C20	1.377 (3)
C4—C9	1.386 (3)	C20—H20	0.95
C5—C6	1.390 (3)	C20—C21	1.373 (3)
C6—H6	0.95	C21—C22	1.385 (3)
C6—C7	1.384 (3)	C22—H22	0.95
C5—O1—C10	116.99 (17)	O1—C10—H10B	109.5
C2—N1—C1	111.42 (17)	O1—C10—H10C	109.5
C11—N1—C1	115.89 (16)	H10A—C10—H10B	109.5
C11—N1—C2	117.62 (17)	H10A—C10—H10C	109.5
N1—C1—H1	106.9	H10B—C10—H10C	109.5
N1—C1—C8	109.67 (16)	N1—C11—C16	124.2 (2)
N1—C1—C17	113.01 (16)	C12—C11—N1	119.7 (2)
C8—C1—H1	106.9	C12—C11—C16	116.1 (2)
C8—C1—C17	112.95 (18)	F1—C12—C11	119.6 (2)
C17—C1—H1	106.9	F1—C12—C13	118.5 (2)
N1—C2—H2A	109.6	C13—C12—C11	121.8 (2)
N1—C2—H2B	109.6	F2—C13—C12	117.9 (2)
N1—C2—C3	110.33 (17)	F2—C13—C14	120.2 (3)
H2A—C2—H2B	108.1	C14—C13—C12	121.9 (2)
C3—C2—H2A	109.6	C13—C14—H14	121.3
C3—C2—H2B	109.6	C13—C14—C15	117.4 (3)
C2—C3—H3A	108.9	C15—C14—H14	121.3
C2—C3—H3B	108.9	C14—C15—H15	119.3
H3A—C3—H3B	107.7	C16—C15—C14	121.4 (2)
C9—C3—C2	113.45 (17)	C16—C15—H15	119.3
C9—C3—H3A	108.9	C11—C16—H16	119.3
C9—C3—H3B	108.9	C15—C16—C11	121.3 (2)
C5—C4—H4	119.4	C15—C16—H16	119.3
C9—C4—H4	119.4	C18—C17—C1	121.1 (2)
C9—C4—C5	121.16 (19)	C18—C17—C22	119.25 (19)
O1—C5—C4	116.16 (19)	C22—C17—C1	119.6 (2)
O1—C5—C6	124.3 (2)	C17—C18—H18	120.6
C6—C5—C4	119.5 (2)	C19—C18—C17	118.8 (2)
C5—C6—H6	120.5	C19—C18—H18	120.6
C7—C6—C5	119.0 (2)	F4—C19—C18	118.0 (2)
C7—C6—H6	120.5	F4—C19—C20	118.15 (19)
C6—C7—H7	118.9	C20—C19—C18	123.8 (2)
C6—C7—C8	122.2 (2)	C19—C20—H20	122.1
C8—C7—H7	118.9	C21—C20—C19	115.9 (2)
C7—C8—C1	119.10 (18)	C21—C20—H20	122.1
C7—C8—C9	118.3 (2)	F3—C21—C20	118.2 (2)
C9—C8—C1	122.58 (19)	F3—C21—C22	118.2 (2)
C4—C9—C3	120.01 (18)	C20—C21—C22	123.5 (2)
C4—C9—C8	119.8 (2)	C17—C22—H22	120.6
C8—C9—C3	120.2 (2)	C21—C22—C17	118.7 (2)
O1—C10—H10A	109.5	C21—C22—H22	120.6
F1—C12—C13—F2	1.3 (3)	C6—C7—C8—C1	−178.86 (18)
F1—C12—C13—C14	−178.59 (18)	C6—C7—C8—C9	−1.2 (3)
F2—C13—C14—C15	−178.14 (18)	C7—C8—C9—C3	−179.01 (17)
F3—C21—C22—C17	−179.45 (16)	C7—C8—C9—C4	2.1 (3)
F4—C19—C20—C21	179.39 (17)	C8—C1—C17—C18	16.2 (2)
O1—C5—C6—C7	179.50 (18)	C8—C1—C17—C22	−162.66 (17)
N1—C1—C8—C7	−159.54 (17)	C9—C4—C5—O1	−178.63 (17)
N1—C1—C8—C9	22.9 (2)	C9—C4—C5—C6	1.0 (3)
N1—C1—C17—C18	−109.0 (2)	C10—O1—C5—C4	170.38 (17)
N1—C1—C17—C22	72.1 (2)	C10—O1—C5—C6	−9.3 (3)
N1—C2—C3—C9	−41.3 (2)	C11—N1—C1—C8	166.97 (16)
N1—C11—C12—F1	−3.0 (3)	C11—N1—C1—C17	−66.0 (2)
N1—C11—C12—C13	176.92 (18)	C11—N1—C2—C3	−156.81 (16)
N1—C11—C16—C15	−178.32 (18)	C11—C12—C13—F2	−178.55 (17)
C1—N1—C2—C3	65.9 (2)	C11—C12—C13—C14	1.5 (3)
C1—N1—C11—C12	−62.1 (2)	C12—C11—C16—C15	2.0 (3)
C1—N1—C11—C16	118.2 (2)	C12—C13—C14—C15	1.8 (3)
C1—C8—C9—C3	−1.4 (3)	C13—C14—C15—C16	−3.2 (3)
C1—C8—C9—C4	179.63 (18)	C14—C15—C16—C11	1.3 (3)
C1—C17—C18—C19	−178.63 (17)	C16—C11—C12—F1	176.77 (17)
C1—C17—C22—C21	178.60 (17)	C16—C11—C12—C13	−3.3 (3)
C2—N1—C1—C8	−55.0 (2)	C17—C1—C8—C7	73.4 (2)
C2—N1—C1—C17	72.0 (2)	C17—C1—C8—C9	−104.1 (2)
C2—N1—C11—C12	162.53 (17)	C17—C18—C19—F4	−179.95 (17)
C2—N1—C11—C16	−17.2 (3)	C17—C18—C19—C20	0.5 (3)
C2—C3—C9—C4	−170.65 (17)	C18—C17—C22—C21	−0.3 (3)
C2—C3—C9—C8	10.4 (3)	C18—C19—C20—C21	−1.0 (3)
C4—C5—C6—C7	−0.1 (3)	C19—C20—C21—F3	−179.93 (17)
C5—C4—C9—C3	179.05 (18)	C19—C20—C21—C22	1.0 (3)
C5—C4—C9—C8	−2.0 (3)	C20—C21—C22—C17	−0.3 (3)
C5—C6—C7—C8	0.2 (3)	C22—C17—C18—C19	0.2 (3)

(6-7)

Crystal data

C22H17F4NO	F(000) = 1600
Mr = 387.36	Dx = 1.468 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3917 reflections
a = 36.448 (11) Å	θ = 3–27.5°
b = 6.1171 (18) Å	µ = 0.12 mm^−1
c = 16.087 (4) Å	T = 100 K
β = 102.193 (7)°	Irregular, clear light colourless
V = 3505.8 (17) Å^3	0.35 × 0.23 × 0.2 mm
Z = 8

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2690 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.060
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −46→46
Tmin = 0.691, Tmax = 1	k = −7→7
11505 measured reflections	l = −20→20
3977 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0708P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3977 reflections	Δρmax = 0.34 e Å^−3
254 parameters	Δρmin = −0.24 e Å^−3

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
F1	0.59602 (3)	0.95814 (18)	0.38999 (7)	0.0261 (3)
F2	0.47742 (3)	0.6285 (2)	0.34858 (9)	0.0373 (4)
F3	0.57829 (3)	0.98567 (19)	0.57399 (7)	0.0277 (3)
F4	0.54055 (3)	0.8947 (2)	0.69409 (8)	0.0318 (3)
O1	0.80288 (4)	0.7269 (2)	0.68283 (9)	0.0253 (3)
N1	0.63080 (4)	0.6142 (3)	0.48493 (9)	0.0186 (4)
C1	0.64523 (5)	0.7681 (3)	0.55582 (11)	0.0185 (4)
H1	0.6388	0.9195	0.5342	0.022*
C2	0.64743 (6)	0.3954 (3)	0.49970 (12)	0.0214 (4)
H2A	0.6349	0.2939	0.4547	0.026*
H2B	0.6441	0.3385	0.5553	0.026*
C3	0.68883 (6)	0.4114 (3)	0.49884 (12)	0.0222 (4)
H3A	0.701	0.2684	0.5152	0.027*
H3B	0.6918	0.4459	0.4405	0.027*
C4	0.74696 (6)	0.5734 (3)	0.59044 (12)	0.0206 (4)
H4	0.7609	0.4565	0.5734	0.025*
C5	0.76521 (6)	0.7311 (3)	0.64615 (12)	0.0202 (4)
C6	0.74498 (6)	0.9051 (3)	0.66921 (12)	0.0228 (4)
H6	0.7575	1.0161	0.7059	0.027*
C7	0.70670 (6)	0.9160 (3)	0.63862 (12)	0.0207 (4)
H7	0.693	1.0345	0.6551	0.025*
C8	0.68763 (6)	0.7553 (3)	0.58351 (12)	0.0195 (4)
C9	0.70817 (6)	0.5857 (3)	0.55933 (11)	0.0195 (4)
C10	0.82382 (6)	0.5440 (4)	0.66357 (13)	0.0273 (5)
H10A	0.8241	0.5444	0.6028	0.041*
H10B	0.8122	0.4086	0.678	0.041*
H10C	0.8496	0.5532	0.6967	0.041*
C11	0.59115 (5)	0.6164 (3)	0.45497 (11)	0.0177 (4)
C12	0.57401 (6)	0.7892 (3)	0.40479 (12)	0.0212 (4)
C13	0.53630 (6)	0.7991 (3)	0.36913 (12)	0.0240 (4)
H13	0.5256	0.9207	0.3359	0.029*
C14	0.51469 (6)	0.6248 (3)	0.38384 (13)	0.0254 (5)
C15	0.52950 (6)	0.4495 (4)	0.43334 (13)	0.0258 (5)
H15	0.5139	0.3318	0.4427	0.031*
C16	0.56768 (6)	0.4474 (3)	0.46939 (12)	0.0216 (4)
H16	0.578	0.3283	0.5046	0.026*
C17	0.62625 (5)	0.7310 (3)	0.63132 (11)	0.0184 (4)
C18	0.59305 (5)	0.8351 (3)	0.63422 (11)	0.0192 (4)
C19	0.57360 (6)	0.7914 (3)	0.69681 (12)	0.0215 (4)
C20	0.58698 (6)	0.6440 (3)	0.76013 (12)	0.0231 (4)
H20	0.5733	0.6134	0.803	0.028*
C21	0.62070 (6)	0.5407 (3)	0.76040 (12)	0.0226 (4)
H21	0.6306	0.44	0.8044	0.027*
C22	0.64016 (6)	0.5831 (3)	0.69697 (11)	0.0203 (4)
H22	0.6633	0.5108	0.698	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0259 (7)	0.0216 (6)	0.0309 (6)	−0.0026 (5)	0.0064 (5)	0.0065 (5)
F2	0.0210 (7)	0.0398 (8)	0.0490 (8)	−0.0017 (6)	0.0025 (6)	0.0009 (6)
F3	0.0339 (7)	0.0257 (7)	0.0255 (6)	0.0111 (5)	0.0108 (5)	0.0080 (5)
F4	0.0275 (7)	0.0383 (8)	0.0329 (7)	0.0127 (6)	0.0136 (6)	0.0039 (6)
O1	0.0210 (8)	0.0246 (8)	0.0297 (7)	−0.0004 (6)	0.0045 (6)	−0.0026 (6)
N1	0.0205 (9)	0.0172 (8)	0.0183 (7)	0.0002 (7)	0.0044 (7)	−0.0019 (6)
C1	0.0219 (11)	0.0150 (9)	0.0200 (9)	0.0003 (8)	0.0073 (8)	−0.0007 (7)
C2	0.0247 (11)	0.0175 (10)	0.0224 (9)	−0.0001 (9)	0.0056 (8)	−0.0016 (8)
C3	0.0239 (11)	0.0192 (10)	0.0236 (9)	0.0023 (8)	0.0053 (8)	−0.0022 (8)
C4	0.0233 (11)	0.0197 (10)	0.0204 (9)	0.0009 (8)	0.0081 (8)	−0.0007 (7)
C5	0.0207 (11)	0.0214 (10)	0.0193 (9)	−0.0024 (8)	0.0057 (8)	0.0025 (7)
C6	0.0275 (11)	0.0203 (10)	0.0223 (9)	−0.0034 (9)	0.0089 (9)	−0.0027 (7)
C7	0.0219 (11)	0.0199 (10)	0.0218 (9)	0.0013 (8)	0.0080 (8)	−0.0001 (8)
C8	0.0220 (11)	0.0184 (10)	0.0197 (9)	−0.0001 (8)	0.0081 (8)	0.0018 (7)
C9	0.0235 (11)	0.0177 (10)	0.0187 (9)	−0.0008 (8)	0.0077 (8)	0.0014 (7)
C10	0.0233 (11)	0.0287 (12)	0.0298 (11)	0.0040 (9)	0.0052 (9)	−0.0008 (9)
C11	0.0199 (10)	0.0184 (10)	0.0155 (8)	0.0014 (8)	0.0055 (8)	−0.0003 (7)
C12	0.0258 (11)	0.0181 (10)	0.0220 (9)	−0.0054 (8)	0.0103 (8)	−0.0016 (8)
C13	0.0223 (11)	0.0238 (11)	0.0252 (10)	0.0022 (9)	0.0036 (8)	0.0019 (8)
C14	0.0179 (11)	0.0300 (12)	0.0278 (10)	−0.0006 (9)	0.0038 (8)	−0.0041 (9)
C15	0.0259 (11)	0.0252 (11)	0.0284 (10)	−0.0041 (9)	0.0106 (9)	−0.0027 (9)
C16	0.0268 (11)	0.0198 (10)	0.0197 (9)	0.0001 (9)	0.0087 (8)	0.0015 (8)
C17	0.0207 (10)	0.0161 (10)	0.0188 (9)	−0.0010 (8)	0.0054 (8)	−0.0014 (7)
C18	0.0227 (11)	0.0172 (10)	0.0173 (9)	0.0031 (8)	0.0034 (8)	0.0025 (7)
C19	0.0190 (10)	0.0225 (10)	0.0237 (9)	0.0032 (8)	0.0060 (8)	−0.0019 (8)
C20	0.0264 (11)	0.0246 (11)	0.0207 (9)	−0.0011 (9)	0.0106 (8)	0.0002 (8)
C21	0.0262 (11)	0.0221 (11)	0.0196 (9)	0.0009 (9)	0.0051 (8)	0.0015 (8)
C22	0.0197 (10)	0.0211 (10)	0.0199 (9)	−0.0013 (8)	0.0039 (8)	−0.0012 (7)

Geometric parameters (Å, º)

F1—C12	1.359 (2)	C7—H7	0.95
F2—C14	1.357 (2)	C7—C8	1.405 (3)
F3—C18	1.363 (2)	C8—C9	1.383 (3)
F4—C19	1.353 (2)	C10—H10A	0.98
O1—C5	1.375 (2)	C10—H10B	0.98
O1—C10	1.425 (2)	C10—H10C	0.98
N1—C1	1.487 (2)	C11—C12	1.395 (3)
N1—C2	1.468 (2)	C11—C16	1.392 (3)
N1—C11	1.423 (2)	C12—C13	1.374 (3)
C1—H1	1	C13—H13	0.95
C1—C8	1.517 (3)	C13—C14	1.376 (3)
C1—C17	1.536 (2)	C14—C15	1.376 (3)
C2—H2A	0.99	C15—H15	0.95
C2—H2B	0.99	C15—C16	1.390 (3)
C2—C3	1.515 (3)	C16—H16	0.95
C3—H3A	0.99	C17—C18	1.377 (3)
C3—H3B	0.99	C17—C22	1.402 (3)
C3—C9	1.513 (3)	C18—C19	1.375 (3)
C4—H4	0.95	C19—C20	1.371 (3)
C4—C5	1.388 (3)	C20—H20	0.95
C4—C9	1.399 (3)	C20—C21	1.381 (3)
C5—C6	1.389 (3)	C21—H21	0.95
C6—H6	0.95	C21—C22	1.385 (3)
C6—C7	1.380 (3)	C22—H22	0.95
C5—O1—C10	116.99 (16)	O1—C10—H10B	109.5
C2—N1—C1	112.72 (15)	O1—C10—H10C	109.5
C11—N1—C1	115.02 (15)	H10A—C10—H10B	109.5
C11—N1—C2	114.75 (16)	H10A—C10—H10C	109.5
N1—C1—H1	107.5	H10B—C10—H10C	109.5
N1—C1—C8	111.47 (15)	C12—C11—N1	120.11 (17)
N1—C1—C17	111.57 (15)	C16—C11—N1	123.50 (17)
C8—C1—H1	107.5	C16—C11—C12	116.32 (18)
C8—C1—C17	111.17 (15)	F1—C12—C11	117.94 (17)
C17—C1—H1	107.5	F1—C12—C13	117.94 (17)
N1—C2—H2A	110	C13—C12—C11	124.12 (18)
N1—C2—H2B	110	C12—C13—H13	121.5
N1—C2—C3	108.53 (16)	C12—C13—C14	116.91 (19)
H2A—C2—H2B	108.4	C14—C13—H13	121.5
C3—C2—H2A	110	F2—C14—C13	118.28 (19)
C3—C2—H2B	110	F2—C14—C15	119.39 (19)
C2—C3—H3A	109.3	C13—C14—C15	122.3 (2)
C2—C3—H3B	109.3	C14—C15—H15	120.5
H3A—C3—H3B	108	C14—C15—C16	118.98 (19)
C9—C3—C2	111.65 (16)	C16—C15—H15	120.5
C9—C3—H3A	109.3	C11—C16—H16	119.3
C9—C3—H3B	109.3	C15—C16—C11	121.32 (19)
C5—C4—H4	119.9	C15—C16—H16	119.3
C5—C4—C9	120.27 (18)	C18—C17—C1	120.28 (16)
C9—C4—H4	119.9	C18—C17—C22	116.96 (17)
O1—C5—C4	124.25 (18)	C22—C17—C1	122.65 (17)
O1—C5—C6	115.97 (17)	F3—C18—C17	120.42 (16)
C4—C5—C6	119.77 (19)	F3—C18—C19	117.71 (17)
C5—C6—H6	120.1	C19—C18—C17	121.87 (17)
C7—C6—C5	119.70 (18)	F4—C19—C18	118.62 (17)
C7—C6—H6	120.1	F4—C19—C20	120.41 (17)
C6—C7—H7	119.4	C20—C19—C18	120.97 (18)
C6—C7—C8	121.28 (18)	C19—C20—H20	120.7
C8—C7—H7	119.4	C19—C20—C21	118.68 (18)
C7—C8—C1	119.11 (17)	C21—C20—H20	120.7
C9—C8—C1	122.30 (18)	C20—C21—H21	119.8
C9—C8—C7	118.53 (18)	C20—C21—C22	120.40 (18)
C4—C9—C3	119.36 (17)	C22—C21—H21	119.8
C8—C9—C3	120.23 (18)	C17—C22—H22	119.5
C8—C9—C4	120.40 (18)	C21—C22—C17	121.08 (18)
O1—C10—H10A	109.5	C21—C22—H22	119.5
F1—C12—C13—C14	178.98 (16)	C6—C7—C8—C1	176.48 (17)
F2—C14—C15—C16	−179.80 (17)	C6—C7—C8—C9	−0.8 (3)
F3—C18—C19—F4	1.8 (3)	C7—C8—C9—C3	−178.92 (17)
F3—C18—C19—C20	−179.14 (18)	C7—C8—C9—C4	1.1 (3)
F4—C19—C20—C21	179.57 (18)	C8—C1—C17—C18	147.59 (18)
O1—C5—C6—C7	−176.82 (16)	C8—C1—C17—C22	−36.3 (2)
N1—C1—C8—C7	168.43 (16)	C9—C4—C5—O1	176.97 (16)
N1—C1—C8—C9	−14.4 (2)	C9—C4—C5—C6	−1.8 (3)
N1—C1—C17—C18	−87.3 (2)	C10—O1—C5—C4	−1.9 (3)
N1—C1—C17—C22	88.8 (2)	C10—O1—C5—C6	176.85 (16)
N1—C2—C3—C9	52.6 (2)	C11—N1—C1—C8	−179.84 (15)
N1—C11—C12—F1	−3.6 (3)	C11—N1—C1—C17	55.2 (2)
N1—C11—C12—C13	176.16 (17)	C11—N1—C2—C3	159.21 (15)
N1—C11—C16—C15	−175.00 (17)	C11—C12—C13—C14	−0.8 (3)
C1—N1—C2—C3	−66.53 (19)	C12—C11—C16—C15	1.9 (3)
C1—N1—C11—C12	74.8 (2)	C12—C13—C14—F2	−179.19 (17)
C1—N1—C11—C16	−108.5 (2)	C12—C13—C14—C15	1.4 (3)
C1—C8—C9—C3	3.9 (3)	C13—C14—C15—C16	−0.4 (3)
C1—C8—C9—C4	−176.13 (16)	C14—C15—C16—C11	−1.3 (3)
C1—C17—C18—F3	−5.5 (3)	C16—C11—C12—F1	179.42 (15)
C1—C17—C18—C19	174.20 (18)	C16—C11—C12—C13	−0.8 (3)
C1—C17—C22—C21	−174.71 (18)	C17—C1—C8—C7	−66.4 (2)
C2—N1—C1—C8	46.0 (2)	C17—C1—C8—C9	110.77 (19)
C2—N1—C1—C17	−78.91 (19)	C17—C18—C19—F4	−177.91 (18)
C2—N1—C11—C12	−152.01 (17)	C17—C18—C19—C20	1.1 (3)
C2—N1—C11—C16	24.7 (2)	C18—C17—C22—C21	1.5 (3)
C2—C3—C9—C4	157.03 (17)	C18—C19—C20—C21	0.5 (3)
C2—C3—C9—C8	−23.0 (2)	C19—C20—C21—C22	−1.1 (3)
C4—C5—C6—C7	2.0 (3)	C20—C21—C22—C17	0.1 (3)
C5—C4—C9—C3	−179.81 (17)	C22—C17—C18—F3	178.16 (16)
C5—C4—C9—C8	0.2 (3)	C22—C17—C18—C19	−2.1 (3)
C5—C6—C7—C8	−0.7 (3)

(6-8)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.446 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4920 reflections
a = 16.559 (2) Å	θ = 3.3–27.5°
b = 17.595 (2) Å	µ = 0.12 mm^−1
c = 6.1048 (9) Å	T = 100 K
V = 1778.7 (4) Å^3	Needle, clear yellowish yellow
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3654 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.041
profile data from ω–scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan Blessing 1995	h = −21→20
Tmin = 0.88, Tmax = 1	k = −22→22
15664 measured reflections	l = −7→7
4061 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.4424P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.106	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.27 e Å^−3
4061 reflections	Δρmin = −0.22 e Å^−3
254 parameters	Absolute structure: Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: −0.1 (4)

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
C19	0.61840 (17)	0.17114 (16)	0.3861 (5)	0.0246 (6)
H19	0.6409	0.1328	0.295	0.03*
C11	0.37187 (16)	0.15200 (16)	0.5475 (5)	0.0214 (5)
C18	0.54189 (16)	0.19998 (15)	0.3514 (5)	0.0221 (5)
C9	0.35821 (15)	0.38841 (15)	0.6540 (5)	0.0213 (5)
C5	0.37694 (18)	0.51749 (16)	0.5279 (5)	0.0250 (6)
C20	0.66008 (17)	0.20134 (18)	0.5611 (5)	0.0281 (6)
C7	0.43560 (17)	0.41391 (15)	0.3281 (5)	0.0238 (6)
H7	0.4668	0.3959	0.2083	0.029*
C17	0.50621 (15)	0.25574 (15)	0.4780 (4)	0.0212 (5)
C4	0.34524 (16)	0.46666 (15)	0.6772 (5)	0.0241 (6)
H4	0.3143	0.485	0.7972	0.029*
C6	0.42307 (18)	0.49102 (16)	0.3519 (5)	0.0262 (6)
H6	0.4456	0.5258	0.2497	0.031*
C14	0.38270 (18)	−0.00207 (16)	0.4610 (5)	0.0288 (6)
C22	0.55278 (16)	0.28447 (15)	0.6496 (5)	0.0238 (6)
H22	0.5311	0.3236	0.7391	0.029*
C13	0.34142 (17)	0.04346 (17)	0.3155 (5)	0.0265 (6)
H13	0.317	0.0231	0.1875	0.032*
C15	0.41810 (19)	0.02594 (17)	0.6464 (5)	0.0311 (7)
H15	0.4456	−0.0069	0.7448	0.037*
C21	0.62983 (16)	0.25752 (16)	0.6932 (5)	0.0265 (6)
H21	0.6607	0.2774	0.8112	0.032*
C16	0.41317 (17)	0.10340 (16)	0.6881 (5)	0.0282 (6)
H16	0.4385	0.1236	0.8151	0.034*
C3	0.32257 (17)	0.33448 (16)	0.8189 (5)	0.0241 (6)
H3A	0.264	0.329	0.7907	0.029*
H3B	0.3294	0.3559	0.9677	0.029*
C2	0.36228 (17)	0.25690 (16)	0.8089 (4)	0.0233 (6)
H2A	0.418	0.2599	0.8668	0.028*
H2B	0.3315	0.2202	0.899	0.028*
C10	0.3247 (2)	0.62382 (18)	0.7232 (6)	0.0354 (7)
H10A	0.3233	0.6794	0.7161	0.053*
H10B	0.3517	0.6079	0.8584	0.053*
H10C	0.2694	0.604	0.7217	0.053*
C12	0.33721 (16)	0.11964 (15)	0.3635 (5)	0.0225 (6)
C8	0.40322 (16)	0.36187 (15)	0.4769 (4)	0.0214 (5)
C1	0.41812 (16)	0.27787 (14)	0.4411 (4)	0.0203 (5)
H1	0.4047	0.2663	0.2849	0.024*
N1	0.36361 (14)	0.23198 (13)	0.5800 (4)	0.0215 (5)
O1	0.36772 (13)	0.59494 (11)	0.5392 (4)	0.0307 (5)
F3	0.49966 (9)	0.17086 (9)	0.1801 (3)	0.0289 (4)
F1	0.29748 (10)	0.16511 (9)	0.2233 (3)	0.0290 (4)
F2	0.38839 (12)	−0.07713 (10)	0.4147 (3)	0.0393 (5)
F4	0.73537 (10)	0.17432 (11)	0.5994 (3)	0.0394 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C19	0.0230 (13)	0.0255 (13)	0.0253 (14)	0.0017 (11)	0.0023 (11)	−0.0011 (11)
C11	0.0179 (12)	0.0232 (12)	0.0230 (13)	−0.0034 (11)	0.0008 (10)	0.0012 (11)
C18	0.0212 (12)	0.0259 (13)	0.0193 (13)	−0.0044 (11)	−0.0012 (11)	0.0013 (11)
C9	0.0216 (12)	0.0207 (13)	0.0216 (13)	−0.0006 (10)	−0.0013 (11)	−0.0001 (11)
C5	0.0286 (14)	0.0227 (13)	0.0237 (13)	0.0034 (11)	−0.0038 (11)	−0.0018 (12)
C20	0.0205 (13)	0.0345 (16)	0.0292 (15)	0.0004 (12)	−0.0021 (12)	0.0060 (13)
C7	0.0240 (13)	0.0260 (14)	0.0213 (13)	0.0020 (11)	0.0017 (11)	0.0016 (11)
C17	0.0211 (13)	0.0215 (12)	0.0210 (13)	−0.0018 (10)	0.0014 (11)	0.0019 (10)
C4	0.0239 (13)	0.0271 (14)	0.0213 (13)	0.0028 (11)	−0.0001 (11)	−0.0037 (12)
C6	0.0292 (14)	0.0234 (13)	0.0259 (14)	−0.0030 (11)	0.0008 (12)	0.0047 (12)
C14	0.0331 (15)	0.0199 (13)	0.0333 (16)	−0.0013 (12)	0.0034 (13)	−0.0011 (13)
C22	0.0241 (13)	0.0231 (13)	0.0242 (14)	−0.0022 (11)	0.0010 (11)	0.0001 (11)
C13	0.0271 (14)	0.0303 (15)	0.0222 (14)	−0.0038 (12)	0.0017 (11)	−0.0019 (12)
C15	0.0343 (15)	0.0262 (15)	0.0327 (16)	0.0027 (12)	−0.0075 (13)	0.0061 (12)
C21	0.0235 (13)	0.0325 (15)	0.0236 (13)	−0.0036 (11)	−0.0046 (12)	0.0000 (12)
C16	0.0279 (14)	0.0279 (14)	0.0289 (14)	−0.0023 (12)	−0.0067 (13)	0.0007 (13)
C3	0.0271 (14)	0.0255 (14)	0.0196 (13)	−0.0001 (11)	0.0041 (11)	−0.0004 (11)
C2	0.0275 (15)	0.0237 (14)	0.0187 (13)	−0.0018 (11)	0.0018 (11)	0.0029 (11)
C10	0.0434 (18)	0.0270 (15)	0.0357 (17)	0.0041 (13)	0.0042 (15)	−0.0070 (14)
C12	0.0219 (13)	0.0251 (13)	0.0206 (13)	−0.0007 (11)	0.0012 (11)	0.0042 (11)
C8	0.0218 (13)	0.0213 (13)	0.0211 (13)	0.0002 (10)	−0.0023 (11)	−0.0010 (11)
C1	0.0203 (13)	0.0223 (12)	0.0181 (12)	0.0001 (10)	−0.0001 (10)	0.0008 (11)
N1	0.0226 (11)	0.0214 (11)	0.0203 (11)	−0.0014 (9)	0.0027 (9)	0.0009 (9)
O1	0.0384 (12)	0.0226 (10)	0.0309 (11)	0.0041 (9)	0.0035 (9)	−0.0023 (9)
F3	0.0255 (8)	0.0359 (9)	0.0252 (8)	0.0002 (7)	−0.0019 (7)	−0.0094 (7)
F1	0.0312 (9)	0.0306 (9)	0.0251 (8)	0.0013 (7)	−0.0062 (7)	0.0029 (7)
F2	0.0521 (12)	0.0218 (8)	0.0441 (12)	0.0016 (8)	−0.0051 (9)	−0.0027 (8)
F4	0.0224 (9)	0.0584 (12)	0.0375 (10)	0.0103 (8)	−0.0057 (8)	0.0008 (9)

Geometric parameters (Å, º)

C19—H19	0.95	C14—C15	1.366 (4)
C19—C18	1.381 (4)	C14—F2	1.354 (3)
C19—C20	1.378 (4)	C22—H22	0.95
C11—C16	1.391 (4)	C22—C21	1.387 (4)
C11—C12	1.384 (4)	C13—H13	0.95
C11—N1	1.428 (3)	C13—C12	1.374 (4)
C18—C17	1.382 (4)	C15—H15	0.95
C18—F3	1.358 (3)	C15—C16	1.389 (4)
C9—C4	1.401 (4)	C21—H21	0.95
C9—C3	1.504 (4)	C16—H16	0.95
C9—C8	1.393 (4)	C3—H3A	0.99
C5—C4	1.381 (4)	C3—H3B	0.99
C5—C6	1.398 (4)	C3—C2	1.516 (4)
C5—O1	1.373 (3)	C2—H2A	0.99
C20—C21	1.371 (4)	C2—H2B	0.99
C20—F4	1.355 (3)	C2—N1	1.465 (3)
C7—H7	0.95	C10—H10A	0.98
C7—C6	1.380 (4)	C10—H10B	0.98
C7—C8	1.397 (4)	C10—H10C	0.98
C17—C22	1.396 (4)	C10—O1	1.424 (4)
C17—C1	1.526 (4)	C12—F1	1.344 (3)
C4—H4	0.95	C8—C1	1.514 (4)
C6—H6	0.95	C1—H1	1
C14—C13	1.378 (4)	C1—N1	1.478 (3)
C18—C19—H19	122.1	C16—C15—H15	120.6
C20—C19—H19	122.1	C20—C21—C22	118.0 (3)
C20—C19—C18	115.9 (3)	C20—C21—H21	121
C16—C11—N1	124.5 (3)	C22—C21—H21	121
C12—C11—C16	116.9 (3)	C11—C16—H16	119.4
C12—C11—N1	118.6 (2)	C15—C16—C11	121.3 (3)
C19—C18—C17	124.6 (3)	C15—C16—H16	119.4
F3—C18—C19	116.9 (2)	C9—C3—H3A	109.3
F3—C18—C17	118.6 (2)	C9—C3—H3B	109.3
C4—C9—C3	119.5 (2)	C9—C3—C2	111.8 (2)
C8—C9—C4	119.3 (3)	H3A—C3—H3B	107.9
C8—C9—C3	121.2 (2)	C2—C3—H3A	109.3
C4—C5—C6	120.0 (3)	C2—C3—H3B	109.3
O1—C5—C4	124.5 (3)	C3—C2—H2A	110
O1—C5—C6	115.5 (3)	C3—C2—H2B	110
C21—C20—C19	123.4 (3)	H2A—C2—H2B	108.4
F4—C20—C19	117.3 (3)	N1—C2—C3	108.3 (2)
F4—C20—C21	119.2 (3)	N1—C2—H2A	110
C6—C7—H7	119.4	N1—C2—H2B	110
C6—C7—C8	121.2 (3)	H10A—C10—H10B	109.5
C8—C7—H7	119.4	H10A—C10—H10C	109.5
C18—C17—C22	116.1 (2)	H10B—C10—H10C	109.5
C18—C17—C1	120.5 (2)	O1—C10—H10A	109.5
C22—C17—C1	123.1 (2)	O1—C10—H10B	109.5
C9—C4—H4	119.6	O1—C10—H10C	109.5
C5—C4—C9	120.8 (3)	C13—C12—C11	123.6 (3)
C5—C4—H4	119.6	F1—C12—C11	118.4 (2)
C5—C6—H6	120.3	F1—C12—C13	118.0 (3)
C7—C6—C5	119.4 (3)	C9—C8—C7	119.4 (3)
C7—C6—H6	120.3	C9—C8—C1	121.8 (2)
C15—C14—C13	122.5 (3)	C7—C8—C1	118.9 (2)
F2—C14—C13	117.8 (3)	C17—C1—H1	107.5
F2—C14—C15	119.7 (3)	C8—C1—C17	112.5 (2)
C17—C22—H22	119	C8—C1—H1	107.5
C21—C22—C17	121.9 (3)	N1—C1—C17	111.1 (2)
C21—C22—H22	119	N1—C1—C8	110.5 (2)
C14—C13—H13	121.5	N1—C1—H1	107.5
C12—C13—C14	117.0 (3)	C11—N1—C2	115.4 (2)
C12—C13—H13	121.5	C11—N1—C1	113.6 (2)
C14—C15—H15	120.6	C2—N1—C1	113.1 (2)
C14—C15—C16	118.7 (3)	C5—O1—C10	116.7 (2)
C19—C18—C17—C22	1.0 (4)	C22—C17—C1—N1	−83.3 (3)
C19—C18—C17—C1	−173.5 (3)	C13—C14—C15—C16	−0.9 (4)
C19—C20—C21—C22	0.9 (5)	C15—C14—C13—C12	0.2 (4)
C18—C19—C20—C21	−1.2 (4)	C16—C11—C12—C13	0.3 (4)
C18—C19—C20—F4	−179.9 (3)	C16—C11—C12—F1	−179.4 (2)
C18—C17—C22—C21	−1.3 (4)	C16—C11—N1—C2	−30.5 (4)
C18—C17—C1—C8	−144.6 (3)	C16—C11—N1—C1	102.4 (3)
C18—C17—C1—N1	90.8 (3)	C3—C9—C4—C5	−179.7 (3)
C9—C3—C2—N1	−49.5 (3)	C3—C9—C8—C7	−179.7 (2)
C9—C8—C1—C17	−110.9 (3)	C3—C9—C8—C1	0.3 (4)
C9—C8—C1—N1	13.9 (4)	C3—C2—N1—C11	−158.8 (2)
C20—C19—C18—C17	0.2 (4)	C3—C2—N1—C1	68.0 (3)
C20—C19—C18—F3	−179.8 (2)	C12—C11—C16—C15	−0.9 (4)
C7—C8—C1—C17	69.1 (3)	C12—C11—N1—C2	149.8 (2)
C7—C8—C1—N1	−166.1 (2)	C12—C11—N1—C1	−77.2 (3)
C17—C22—C21—C20	0.4 (4)	C8—C9—C4—C5	−0.4 (4)
C17—C1—N1—C11	−57.0 (3)	C8—C9—C3—C2	17.8 (4)
C17—C1—N1—C2	77.1 (3)	C8—C7—C6—C5	−0.2 (4)
C4—C9—C3—C2	−162.9 (2)	C8—C1—N1—C11	177.4 (2)
C4—C9—C8—C7	1.0 (4)	C8—C1—N1—C2	−48.5 (3)
C4—C9—C8—C1	−179.0 (2)	C1—C17—C22—C21	173.1 (3)
C4—C5—C6—C7	0.8 (4)	N1—C11—C16—C15	179.5 (3)
C4—C5—O1—C10	2.3 (4)	N1—C11—C12—C13	179.9 (3)
C6—C5—C4—C9	−0.5 (4)	N1—C11—C12—F1	0.2 (4)
C6—C5—O1—C10	−176.7 (3)	O1—C5—C4—C9	−179.5 (3)
C6—C7—C8—C9	−0.7 (4)	O1—C5—C6—C7	179.8 (3)
C6—C7—C8—C1	179.3 (3)	F3—C18—C17—C22	−179.0 (2)
C14—C13—C12—C11	0.1 (4)	F3—C18—C17—C1	6.5 (4)
C14—C13—C12—F1	179.8 (2)	F2—C14—C13—C12	−179.1 (2)
C14—C15—C16—C11	1.2 (4)	F2—C14—C15—C16	178.5 (3)
C22—C17—C1—C8	41.3 (3)	F4—C20—C21—C22	179.6 (3)

(6-9)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.449 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4135 reflections
a = 9.445 (6) Å	θ = 3–27.5°
b = 21.293 (11) Å	µ = 0.12 mm^−1
c = 9.590 (6) Å	T = 100 K
β = 112.96 (2)°	Plate, clear light colourless
V = 1775.9 (18) Å^3	0.2 × 0.2 × 0.01 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2419 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.062
profile data from ω–scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan Blessing 1995	h = −11→11
Tmin = 0.79, Tmax = 1	k = −25→25
9543 measured reflections	l = −11→10
3113 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.072	H-atom parameters constrained
wR(F^2) = 0.216	w = 1/[σ^2(Fo^2) + (0.1384P)^2 + 0.3392P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3113 reflections	Δρmax = 0.60 e Å^−3
254 parameters	Δρmin = −0.36 e Å^−3

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
C19	0.2389 (3)	0.72638 (11)	0.3398 (3)	0.0299 (6)
H19	0.2806	0.7533	0.2864	0.036*
C18	0.3151 (3)	0.67234 (12)	0.4077 (3)	0.0273 (6)
C1	0.3425 (3)	0.56909 (11)	0.5492 (3)	0.0270 (6)
H1	0.4531	0.5732	0.5647	0.032*
C22	0.1219 (3)	0.64534 (11)	0.4955 (3)	0.0291 (6)
H22	0.0794	0.6182	0.5477	0.035*
C5	0.1580 (3)	0.41691 (12)	0.2322 (3)	0.0306 (6)
C20	0.1007 (3)	0.74069 (12)	0.3508 (3)	0.0326 (6)
H20	0.045	0.7775	0.3054	0.039*
C7	0.2454 (3)	0.52290 (12)	0.2881 (3)	0.0294 (6)
H7	0.2672	0.5624	0.2549	0.035*
C21	0.0466 (3)	0.69961 (12)	0.4298 (3)	0.0328 (6)
C9	0.2384 (3)	0.45655 (12)	0.4871 (3)	0.0293 (6)
C16	0.5197 (3)	0.64586 (12)	0.8027 (3)	0.0309 (6)
H16	0.5483	0.6444	0.7182	0.037*
C6	0.1882 (3)	0.47471 (12)	0.1832 (3)	0.0312 (6)
H6	0.17	0.4813	0.0796	0.037*
C2	0.3783 (3)	0.49289 (12)	0.7516 (3)	0.0314 (6)
H2A	0.3847	0.4888	0.8567	0.038*
H2B	0.4807	0.4832	0.7513	0.038*
C4	0.1858 (3)	0.40822 (12)	0.3837 (3)	0.0318 (6)
H4	0.1682	0.3681	0.4173	0.038*
C3	0.2608 (3)	0.44734 (12)	0.6501 (3)	0.0345 (6)
H3A	0.2954	0.4038	0.6815	0.041*
H3B	0.1617	0.4537	0.6607	0.041*
C15	0.5895 (3)	0.68986 (13)	0.9158 (3)	0.0356 (7)
H15	0.6631	0.7188	0.9087	0.043*
C12	0.3715 (3)	0.60883 (13)	0.9355 (3)	0.0360 (7)
C13	0.4400 (4)	0.65073 (14)	1.0511 (3)	0.0411 (7)
H13	0.4132	0.6523	1.1367	0.049*
C14	0.5482 (3)	0.68998 (14)	1.0382 (3)	0.0396 (7)
C10	0.0588 (4)	0.37515 (14)	−0.0185 (3)	0.0444 (8)
H10A	0.0229	0.3353	−0.0718	0.067*
H10B	0.1465	0.3906	−0.0389	0.067*
H10C	−0.0246	0.4061	−0.0539	0.067*
C17	0.2605 (3)	0.63054 (11)	0.4850 (3)	0.0263 (6)
C11	0.4096 (3)	0.60381 (12)	0.8088 (3)	0.0285 (6)
C8	0.2717 (3)	0.51507 (12)	0.4398 (3)	0.0283 (6)
N1	0.3335 (2)	0.55777 (9)	0.6968 (2)	0.0272 (5)
O1	0.1045 (2)	0.36568 (9)	0.1400 (2)	0.0363 (5)
F3	0.45171 (17)	0.65968 (7)	0.39668 (17)	0.0336 (4)
F4	−0.08722 (18)	0.71384 (7)	0.4449 (2)	0.0442 (5)
F1	0.26065 (19)	0.57040 (8)	0.94415 (18)	0.0446 (5)
F2	0.6162 (2)	0.73273 (9)	1.15037 (19)	0.0563 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C19	0.0393 (15)	0.0281 (13)	0.0219 (13)	−0.0028 (11)	0.0115 (11)	0.0017 (10)
C18	0.0291 (13)	0.0317 (13)	0.0210 (13)	0.0011 (10)	0.0098 (10)	−0.0039 (10)
C1	0.0306 (13)	0.0272 (12)	0.0243 (14)	0.0025 (10)	0.0119 (10)	0.0007 (10)
C22	0.0322 (14)	0.0286 (13)	0.0275 (14)	0.0008 (10)	0.0129 (11)	0.0014 (10)
C5	0.0275 (13)	0.0269 (13)	0.0361 (16)	−0.0005 (10)	0.0109 (11)	−0.0043 (11)
C20	0.0399 (15)	0.0266 (13)	0.0302 (15)	0.0023 (11)	0.0123 (12)	0.0046 (10)
C7	0.0343 (14)	0.0266 (13)	0.0272 (14)	0.0004 (11)	0.0121 (11)	−0.0011 (10)
C21	0.0327 (14)	0.0314 (14)	0.0374 (15)	0.0032 (11)	0.0170 (11)	0.0013 (11)
C9	0.0309 (13)	0.0281 (13)	0.0321 (15)	0.0036 (11)	0.0157 (11)	0.0028 (10)
C16	0.0314 (14)	0.0364 (14)	0.0256 (14)	0.0056 (11)	0.0119 (11)	−0.0002 (10)
C6	0.0358 (14)	0.0284 (13)	0.0295 (15)	−0.0012 (11)	0.0128 (11)	−0.0001 (10)
C2	0.0391 (15)	0.0296 (13)	0.0267 (14)	0.0037 (11)	0.0143 (12)	0.0043 (11)
C4	0.0313 (13)	0.0273 (13)	0.0382 (16)	−0.0025 (11)	0.0149 (12)	0.0007 (11)
C3	0.0414 (15)	0.0311 (13)	0.0332 (15)	0.0000 (12)	0.0170 (12)	0.0074 (11)
C15	0.0365 (15)	0.0386 (15)	0.0283 (15)	0.0025 (12)	0.0089 (12)	−0.0032 (12)
C12	0.0457 (16)	0.0365 (14)	0.0285 (15)	0.0057 (13)	0.0173 (12)	0.0071 (11)
C13	0.0574 (19)	0.0425 (16)	0.0245 (15)	0.0112 (14)	0.0173 (13)	0.0035 (11)
C14	0.0516 (18)	0.0383 (15)	0.0206 (14)	0.0107 (13)	0.0049 (12)	−0.0023 (11)
C10	0.0498 (17)	0.0356 (16)	0.0372 (17)	0.0035 (13)	0.0054 (13)	−0.0069 (12)
C17	0.0313 (13)	0.0278 (12)	0.0199 (13)	0.0004 (10)	0.0102 (10)	0.0004 (10)
C11	0.0351 (13)	0.0304 (13)	0.0208 (13)	0.0071 (11)	0.0116 (11)	0.0048 (10)
C8	0.0294 (13)	0.0294 (13)	0.0301 (15)	0.0006 (10)	0.0158 (11)	0.0008 (10)
N1	0.0346 (11)	0.0251 (11)	0.0244 (12)	0.0018 (8)	0.0142 (9)	0.0030 (8)
O1	0.0422 (11)	0.0298 (10)	0.0379 (12)	−0.0041 (8)	0.0166 (9)	−0.0057 (8)
F3	0.0362 (9)	0.0368 (9)	0.0337 (9)	−0.0003 (6)	0.0202 (7)	0.0027 (6)
F4	0.0376 (9)	0.0400 (10)	0.0629 (12)	0.0128 (7)	0.0282 (8)	0.0132 (8)
F1	0.0589 (11)	0.0449 (10)	0.0422 (11)	0.0034 (8)	0.0328 (9)	0.0085 (7)
F2	0.0775 (13)	0.0525 (11)	0.0308 (10)	0.0030 (10)	0.0123 (9)	−0.0133 (8)

Geometric parameters (Å, º)

C19—H19	0.95	C16—H16	0.95
C19—C18	1.378 (4)	C16—C15	1.389 (4)
C19—C20	1.384 (4)	C16—C11	1.391 (4)
C18—C17	1.380 (4)	C6—H6	0.95
C18—F3	1.362 (3)	C2—H2A	0.99
C1—H1	1	C2—H2B	0.99
C1—C17	1.523 (3)	C2—C3	1.509 (4)
C1—C8	1.524 (3)	C2—N1	1.480 (3)
C1—N1	1.471 (3)	C4—H4	0.95
C22—H22	0.95	C3—H3A	0.99
C22—C21	1.374 (4)	C3—H3B	0.99
C22—C17	1.388 (4)	C15—H15	0.95
C5—C6	1.386 (4)	C15—C14	1.374 (4)
C5—C4	1.385 (4)	C12—C13	1.373 (4)
C5—O1	1.371 (3)	C12—C11	1.399 (4)
C20—H20	0.95	C12—F1	1.356 (3)
C20—C21	1.380 (4)	C13—H13	0.95
C7—H7	0.95	C13—C14	1.362 (5)
C7—C6	1.391 (4)	C14—F2	1.364 (3)
C7—C8	1.387 (4)	C10—H10A	0.98
C21—F4	1.362 (3)	C10—H10B	0.98
C9—C4	1.380 (4)	C10—H10C	0.98
C9—C3	1.507 (4)	C10—O1	1.423 (4)
C9—C8	1.403 (4)	C11—N1	1.424 (3)
C18—C19—H19	120.6	N1—C2—C3	109.6 (2)
C18—C19—C20	118.8 (2)	C5—C4—H4	119.3
C20—C19—H19	120.6	C9—C4—C5	121.5 (2)
C19—C18—C17	123.8 (2)	C9—C4—H4	119.3
F3—C18—C19	117.6 (2)	C9—C3—C2	110.8 (2)
F3—C18—C17	118.5 (2)	C9—C3—H3A	109.5
C17—C1—H1	108.7	C9—C3—H3B	109.5
C17—C1—C8	110.7 (2)	C2—C3—H3A	109.5
C8—C1—H1	108.7	C2—C3—H3B	109.5
N1—C1—H1	108.7	H3A—C3—H3B	108.1
N1—C1—C17	108.59 (19)	C16—C15—H15	121.3
N1—C1—C8	111.4 (2)	C14—C15—C16	117.5 (3)
C21—C22—H22	120.3	C14—C15—H15	121.3
C21—C22—C17	119.4 (2)	C13—C12—C11	123.4 (3)
C17—C22—H22	120.3	F1—C12—C13	118.3 (2)
C4—C5—C6	119.7 (2)	F1—C12—C11	118.3 (2)
O1—C5—C6	124.1 (2)	C12—C13—H13	121.3
O1—C5—C4	116.2 (2)	C14—C13—C12	117.4 (3)
C19—C20—H20	121.1	C14—C13—H13	121.3
C21—C20—C19	117.7 (2)	C13—C14—C15	123.3 (3)
C21—C20—H20	121.1	C13—C14—F2	118.5 (3)
C6—C7—H7	119	F2—C14—C15	118.2 (3)
C8—C7—H7	119	H10A—C10—H10B	109.5
C8—C7—C6	122.0 (2)	H10A—C10—H10C	109.5
C22—C21—C20	123.3 (3)	H10B—C10—H10C	109.5
F4—C21—C22	118.3 (2)	O1—C10—H10A	109.5
F4—C21—C20	118.4 (2)	O1—C10—H10B	109.5
C4—C9—C3	120.9 (2)	O1—C10—H10C	109.5
C4—C9—C8	119.6 (2)	C18—C17—C1	122.3 (2)
C8—C9—C3	119.5 (2)	C18—C17—C22	116.9 (2)
C15—C16—H16	118.8	C22—C17—C1	120.7 (2)
C15—C16—C11	122.4 (2)	C16—C11—C12	115.9 (2)
C11—C16—H16	118.8	C16—C11—N1	125.2 (2)
C5—C6—C7	118.9 (3)	C12—C11—N1	118.8 (2)
C5—C6—H6	120.6	C7—C8—C1	118.8 (2)
C7—C6—H6	120.6	C7—C8—C9	118.3 (2)
H2A—C2—H2B	108.2	C9—C8—C1	122.7 (2)
C3—C2—H2A	109.8	C1—N1—C2	112.24 (19)
C3—C2—H2B	109.8	C11—N1—C1	114.3 (2)
N1—C2—H2A	109.8	C11—N1—C2	112.6 (2)
N1—C2—H2B	109.8	C5—O1—C10	117.3 (2)
C19—C18—C17—C1	175.7 (2)	C12—C11—N1—C1	161.2 (2)
C19—C18—C17—C22	−1.1 (4)	C12—C11—N1—C2	−69.2 (3)
C19—C20—C21—C22	−0.9 (4)	C13—C12—C11—C16	−2.1 (4)
C19—C20—C21—F4	178.4 (2)	C13—C12—C11—N1	178.7 (2)
C18—C19—C20—C21	0.0 (4)	C17—C1—C8—C7	47.6 (3)
C20—C19—C18—C17	1.0 (4)	C17—C1—C8—C9	−135.4 (2)
C20—C19—C18—F3	−179.3 (2)	C17—C1—N1—C2	167.02 (19)
C21—C22—C17—C18	0.1 (4)	C17—C1—N1—C11	−63.1 (3)
C21—C22—C17—C1	−176.7 (2)	C17—C22—C21—C20	0.9 (4)
C16—C15—C14—C13	−2.0 (4)	C17—C22—C21—F4	−178.4 (2)
C16—C15—C14—F2	179.7 (2)	C11—C16—C15—C14	1.3 (4)
C16—C11—N1—C1	−18.0 (3)	C11—C12—C13—C14	1.5 (4)
C16—C11—N1—C2	111.7 (3)	C8—C1—C17—C18	−96.1 (3)
C6—C5—C4—C9	2.1 (4)	C8—C1—C17—C22	80.6 (3)
C6—C5—O1—C10	−8.4 (4)	C8—C1—N1—C2	44.9 (3)
C6—C7—C8—C1	176.8 (2)	C8—C1—N1—C11	174.77 (19)
C6—C7—C8—C9	−0.3 (4)	C8—C7—C6—C5	−0.7 (4)
C4—C5—C6—C7	−0.2 (4)	C8—C9—C4—C5	−3.1 (4)
C4—C5—O1—C10	173.1 (2)	C8—C9—C3—C2	−24.7 (3)
C4—C9—C3—C2	155.2 (2)	N1—C1—C17—C18	141.4 (2)
C4—C9—C8—C1	−174.9 (2)	N1—C1—C17—C22	−42.0 (3)
C4—C9—C8—C7	2.1 (4)	N1—C1—C8—C7	168.5 (2)
C3—C9—C4—C5	177.0 (2)	N1—C1—C8—C9	−14.5 (3)
C3—C9—C8—C1	5.0 (4)	N1—C2—C3—C9	54.3 (3)
C3—C9—C8—C7	−177.9 (2)	O1—C5—C6—C7	−178.6 (2)
C3—C2—N1—C1	−67.2 (3)	O1—C5—C4—C9	−179.4 (2)
C3—C2—N1—C11	162.1 (2)	F3—C18—C17—C1	−4.0 (3)
C15—C16—C11—C12	0.7 (4)	F3—C18—C17—C22	179.2 (2)
C15—C16—C11—N1	179.8 (2)	F1—C12—C13—C14	−178.3 (2)
C12—C13—C14—C15	0.7 (4)	F1—C12—C11—C16	177.7 (2)
C12—C13—C14—F2	179.0 (2)	F1—C12—C11—N1	−1.5 (4)

(6-13)

Crystal data

C22H17F4NO	F(000) = 1600
Mr = 387.36	Dx = 1.472 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4840 reflections
a = 36.079 (4) Å	θ = 3–27.5°
b = 6.2372 (6) Å	µ = 0.12 mm^−1
c = 16.051 (2) Å	T = 100 K
β = 104.627 (6)°	Irregular, clear light colourless
V = 3495.0 (7) Å^3	0.25 × 0.19 × 0.18 mm
Z = 8

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3509 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.077
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan Blessing 1995	h = −45→46
Tmin = 0.878, Tmax = 1	k = −8→8
11954 measured reflections	l = −20→20
3975 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 3.0682P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3975 reflections	Δρmax = 0.25 e Å^−3
254 parameters	Δρmin = −0.26 e Å^−3

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
F1	0.40659 (2)	0.96899 (12)	0.60233 (5)	0.02346 (19)
F2	0.49708 (2)	0.29704 (14)	0.57062 (6)	0.0289 (2)
F3	0.41588 (2)	1.02214 (13)	0.41797 (5)	0.0261 (2)
F4	0.45258 (2)	0.95718 (14)	0.29622 (5)	0.0283 (2)
O1	0.19366 (3)	0.71075 (15)	0.31545 (6)	0.0226 (2)
N1	0.37123 (3)	0.61245 (16)	0.51699 (6)	0.0163 (2)
C1	0.35526 (3)	0.7614 (2)	0.44466 (7)	0.0163 (2)
H1	0.3614	0.9105	0.4667	0.02*
C2	0.35482 (4)	0.3968 (2)	0.50391 (8)	0.0184 (3)
H2A	0.3684	0.3009	0.5509	0.022*
H2B	0.3577	0.3377	0.4486	0.022*
C3	0.31268 (4)	0.4096 (2)	0.50305 (8)	0.0195 (3)
H3A	0.3006	0.268	0.4869	0.023*
H3B	0.3103	0.4449	0.5616	0.023*
C4	0.25203 (4)	0.5632 (2)	0.40895 (8)	0.0184 (3)
H4	0.2384	0.449	0.4269	0.022*
C5	0.23236 (4)	0.7157 (2)	0.35167 (8)	0.0186 (3)
C6	0.25224 (4)	0.8863 (2)	0.32677 (8)	0.0206 (3)
H6	0.2389	0.9931	0.2886	0.025*
C7	0.29156 (4)	0.8982 (2)	0.35813 (8)	0.0194 (3)
H7	0.3051	1.0136	0.3407	0.023*
C8	0.31198 (3)	0.7440 (2)	0.41502 (8)	0.0169 (2)
C9	0.29191 (4)	0.5766 (2)	0.44053 (8)	0.0175 (3)
C10	0.17291 (4)	0.5354 (2)	0.33851 (9)	0.0245 (3)
H10A	0.1461	0.5435	0.3057	0.037*
H10B	0.1743	0.542	0.4002	0.037*
H10C	0.1841	0.4002	0.3254	0.037*
C11	0.41173 (4)	0.6206 (2)	0.54818 (8)	0.0167 (2)
C12	0.42922 (4)	0.8014 (2)	0.59277 (8)	0.0190 (3)
C13	0.46804 (4)	0.8173 (2)	0.62809 (8)	0.0230 (3)
H13	0.4786	0.945	0.6567	0.028*
C14	0.49164 (4)	0.6453 (2)	0.62164 (9)	0.0236 (3)
H14	0.5185	0.6509	0.6465	0.028*
C15	0.47472 (4)	0.4669 (2)	0.57801 (9)	0.0213 (3)
C16	0.43579 (4)	0.4508 (2)	0.54050 (8)	0.0189 (3)
H16	0.4256	0.325	0.5098	0.023*
C17	0.37407 (3)	0.7286 (2)	0.37002 (7)	0.0164 (2)
C18	0.40455 (4)	0.8567 (2)	0.36345 (8)	0.0182 (3)
C19	0.42391 (4)	0.8227 (2)	0.30045 (8)	0.0201 (3)
C20	0.41389 (4)	0.6577 (2)	0.24259 (8)	0.0223 (3)
H20	0.4278	0.6314	0.2007	0.027*
C21	0.38285 (4)	0.5299 (2)	0.24660 (8)	0.0223 (3)
H21	0.3751	0.4168	0.2063	0.027*
C22	0.36300 (4)	0.5657 (2)	0.30887 (8)	0.0193 (3)
H22	0.3416	0.4784	0.31	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0225 (4)	0.0197 (4)	0.0275 (4)	0.0014 (3)	0.0052 (3)	−0.0053 (3)
F2	0.0226 (4)	0.0277 (4)	0.0378 (5)	0.0072 (3)	0.0103 (4)	0.0009 (4)
F3	0.0326 (5)	0.0236 (4)	0.0242 (4)	−0.0129 (3)	0.0109 (4)	−0.0077 (3)
F4	0.0238 (4)	0.0372 (5)	0.0257 (4)	−0.0128 (3)	0.0098 (3)	−0.0007 (3)
O1	0.0162 (5)	0.0235 (5)	0.0270 (5)	0.0002 (4)	0.0034 (4)	0.0038 (4)
N1	0.0156 (5)	0.0153 (5)	0.0171 (5)	−0.0005 (4)	0.0026 (4)	0.0020 (4)
C1	0.0182 (6)	0.0145 (6)	0.0164 (5)	0.0003 (4)	0.0047 (5)	0.0013 (4)
C2	0.0189 (6)	0.0161 (6)	0.0192 (6)	−0.0005 (5)	0.0030 (5)	0.0020 (4)
C3	0.0186 (6)	0.0180 (6)	0.0217 (6)	−0.0007 (5)	0.0049 (5)	0.0045 (5)
C4	0.0190 (6)	0.0180 (6)	0.0195 (6)	−0.0007 (5)	0.0071 (5)	0.0011 (5)
C5	0.0159 (6)	0.0209 (6)	0.0193 (6)	0.0019 (5)	0.0048 (5)	−0.0014 (5)
C6	0.0216 (6)	0.0196 (6)	0.0210 (6)	0.0027 (5)	0.0058 (5)	0.0034 (5)
C7	0.0219 (6)	0.0170 (6)	0.0204 (6)	0.0002 (5)	0.0075 (5)	0.0025 (5)
C8	0.0171 (6)	0.0177 (6)	0.0162 (5)	0.0007 (4)	0.0050 (5)	−0.0008 (4)
C9	0.0188 (6)	0.0177 (6)	0.0166 (5)	0.0010 (5)	0.0055 (5)	0.0000 (5)
C10	0.0181 (6)	0.0246 (7)	0.0300 (7)	−0.0028 (5)	0.0046 (5)	0.0019 (5)
C11	0.0173 (6)	0.0189 (6)	0.0144 (5)	−0.0017 (5)	0.0048 (5)	0.0021 (4)
C12	0.0204 (6)	0.0185 (6)	0.0189 (6)	0.0020 (5)	0.0064 (5)	0.0001 (5)
C13	0.0215 (7)	0.0243 (7)	0.0226 (6)	−0.0049 (5)	0.0046 (5)	−0.0028 (5)
C14	0.0155 (6)	0.0304 (7)	0.0244 (6)	−0.0017 (5)	0.0038 (5)	0.0012 (5)
C15	0.0208 (6)	0.0225 (7)	0.0222 (6)	0.0040 (5)	0.0085 (5)	0.0028 (5)
C16	0.0208 (6)	0.0185 (6)	0.0184 (6)	−0.0012 (5)	0.0067 (5)	−0.0001 (5)
C17	0.0173 (6)	0.0163 (6)	0.0154 (5)	0.0006 (4)	0.0037 (5)	0.0014 (4)
C18	0.0193 (6)	0.0179 (6)	0.0163 (5)	−0.0024 (5)	0.0023 (5)	−0.0010 (5)
C19	0.0156 (6)	0.0252 (7)	0.0193 (6)	−0.0040 (5)	0.0042 (5)	0.0033 (5)
C20	0.0224 (6)	0.0277 (7)	0.0183 (6)	0.0014 (5)	0.0080 (5)	0.0004 (5)
C21	0.0260 (7)	0.0220 (7)	0.0190 (6)	−0.0017 (5)	0.0056 (5)	−0.0029 (5)
C22	0.0200 (6)	0.0189 (6)	0.0190 (6)	−0.0030 (5)	0.0046 (5)	0.0000 (5)

Geometric parameters (Å, º)

F1—C12	1.3589 (15)	C7—H7	0.95
F2—C15	1.3545 (15)	C7—C8	1.4007 (17)
F3—C18	1.3478 (14)	C8—C9	1.3896 (17)
F4—C19	1.3467 (14)	C10—H10A	0.98
O1—C5	1.3706 (15)	C10—H10B	0.98
O1—C10	1.4259 (16)	C10—H10C	0.98
N1—C1	1.4848 (15)	C11—C12	1.3976 (18)
N1—C2	1.4635 (16)	C11—C16	1.3947 (18)
N1—C11	1.4209 (16)	C12—C13	1.3755 (18)
C1—H1	1	C13—H13	0.95
C1—C8	1.5172 (17)	C13—C14	1.3897 (19)
C1—C17	1.5324 (16)	C14—H14	0.95
C2—H2A	0.99	C14—C15	1.373 (2)
C2—H2B	0.99	C15—C16	1.3850 (19)
C2—C3	1.5189 (17)	C16—H16	0.95
C3—H3A	0.99	C17—C18	1.3847 (17)
C3—H3B	0.99	C17—C22	1.3990 (17)
C3—C9	1.5082 (17)	C18—C19	1.3828 (18)
C4—H4	0.95	C19—C20	1.3722 (19)
C4—C5	1.3875 (18)	C20—H20	0.95
C4—C9	1.4020 (18)	C20—C21	1.3892 (19)
C5—C6	1.3966 (18)	C21—H21	0.95
C6—H6	0.95	C21—C22	1.3868 (18)
C6—C7	1.3825 (18)	C22—H22	0.95
C5—O1—C10	116.91 (10)	O1—C10—H10B	109.5
C2—N1—C1	113.57 (10)	O1—C10—H10C	109.5
C11—N1—C1	114.49 (9)	H10A—C10—H10B	109.5
C11—N1—C2	115.24 (10)	H10A—C10—H10C	109.5
N1—C1—H1	107.3	H10B—C10—H10C	109.5
N1—C1—C8	111.46 (10)	C12—C11—N1	120.04 (11)
N1—C1—C17	111.53 (10)	C16—C11—N1	123.32 (11)
C8—C1—H1	107.3	C16—C11—C12	116.57 (12)
C8—C1—C17	111.68 (10)	F1—C12—C11	118.16 (11)
C17—C1—H1	107.3	F1—C12—C13	118.43 (11)
N1—C2—H2A	109.9	C13—C12—C11	123.40 (12)
N1—C2—H2B	109.9	C12—C13—H13	120.2
N1—C2—C3	108.71 (10)	C12—C13—C14	119.52 (12)
H2A—C2—H2B	108.3	C14—C13—H13	120.2
C3—C2—H2A	109.9	C13—C14—H14	121.2
C3—C2—H2B	109.9	C15—C14—C13	117.51 (12)
C2—C3—H3A	109.3	C15—C14—H14	121.2
C2—C3—H3B	109.3	F2—C15—C14	118.72 (12)
H3A—C3—H3B	107.9	F2—C15—C16	117.79 (12)
C9—C3—C2	111.74 (10)	C14—C15—C16	123.49 (12)
C9—C3—H3A	109.3	C11—C16—H16	120.3
C9—C3—H3B	109.3	C15—C16—C11	119.48 (12)
C5—C4—H4	119.8	C15—C16—H16	120.3
C5—C4—C9	120.33 (12)	C18—C17—C1	119.98 (11)
C9—C4—H4	119.8	C18—C17—C22	117.20 (11)
O1—C5—C4	124.16 (12)	C22—C17—C1	122.75 (11)
O1—C5—C6	115.96 (11)	F3—C18—C17	120.57 (11)
C4—C5—C6	119.88 (12)	F3—C18—C19	117.78 (11)
C5—C6—H6	120.3	C19—C18—C17	121.64 (12)
C7—C6—C5	119.40 (12)	F4—C19—C18	118.51 (12)
C7—C6—H6	120.3	F4—C19—C20	120.51 (11)
C6—C7—H7	119.2	C20—C19—C18	120.98 (12)
C6—C7—C8	121.51 (12)	C19—C20—H20	120.8
C8—C7—H7	119.2	C19—C20—C21	118.47 (12)
C7—C8—C1	119.04 (11)	C21—C20—H20	120.8
C9—C8—C1	122.21 (11)	C20—C21—H21	119.7
C9—C8—C7	118.72 (12)	C22—C21—C20	120.66 (12)
C4—C9—C3	119.42 (11)	C22—C21—H21	119.7
C8—C9—C3	120.44 (11)	C17—C22—H22	119.5
C8—C9—C4	120.13 (12)	C21—C22—C17	120.99 (12)
O1—C10—H10A	109.5	C21—C22—H22	119.5
F1—C12—C13—C14	177.89 (11)	C6—C7—C8—C1	177.81 (11)
F2—C15—C16—C11	178.74 (11)	C6—C7—C8—C9	−0.43 (18)
F3—C18—C19—F4	−0.79 (18)	C7—C8—C9—C3	−178.80 (11)
F3—C18—C19—C20	−179.83 (12)	C7—C8—C9—C4	0.50 (18)
F4—C19—C20—C21	−176.67 (12)	C8—C1—C17—C18	138.96 (12)
O1—C5—C6—C7	−177.71 (11)	C8—C1—C17—C22	−44.17 (16)
N1—C1—C8—C7	168.77 (10)	C9—C4—C5—O1	177.70 (11)
N1—C1—C8—C9	−13.06 (16)	C9—C4—C5—C6	−1.43 (18)
N1—C1—C17—C18	−95.58 (13)	C10—O1—C5—C4	−0.49 (18)
N1—C1—C17—C22	81.28 (14)	C10—O1—C5—C6	178.67 (11)
N1—C2—C3—C9	51.85 (14)	C11—N1—C1—C8	−179.87 (10)
N1—C11—C12—F1	−2.27 (17)	C11—N1—C1—C17	54.55 (13)
N1—C11—C12—C13	177.08 (11)	C11—N1—C2—C3	159.49 (10)
N1—C11—C16—C15	−175.53 (11)	C11—C12—C13—C14	−1.4 (2)
C1—N1—C2—C3	−65.64 (13)	C12—C11—C16—C15	1.37 (17)
C1—N1—C11—C12	69.51 (14)	C12—C13—C14—C15	1.31 (19)
C1—N1—C11—C16	−113.70 (13)	C13—C14—C15—F2	179.88 (11)
C1—C8—C9—C3	3.02 (18)	C13—C14—C15—C16	0.1 (2)
C1—C8—C9—C4	−177.67 (11)	C14—C15—C16—C11	−1.53 (19)
C1—C17—C18—F3	−5.58 (18)	C16—C11—C12—F1	−179.27 (10)
C1—C17—C18—C19	175.56 (11)	C16—C11—C12—C13	0.07 (18)
C1—C17—C22—C21	−174.48 (12)	C17—C1—C8—C7	−65.74 (14)
C2—N1—C1—C8	44.91 (13)	C17—C1—C8—C9	112.43 (13)
C2—N1—C1—C17	−80.66 (12)	C17—C18—C19—F4	178.10 (11)
C2—N1—C11—C12	−156.04 (11)	C17—C18—C19—C20	−0.9 (2)
C2—N1—C11—C16	20.76 (16)	C18—C17—C22—C21	2.47 (19)
C2—C3—C9—C4	158.27 (11)	C18—C19—C20—C21	2.4 (2)
C2—C3—C9—C8	−22.42 (16)	C19—C20—C21—C22	−1.3 (2)
C4—C5—C6—C7	1.49 (19)	C20—C21—C22—C17	−1.1 (2)
C5—C4—C9—C3	179.73 (11)	C22—C17—C18—F3	177.39 (11)
C5—C4—C9—C8	0.42 (18)	C22—C17—C18—C19	−1.48 (19)
C5—C6—C7—C8	−0.57 (19)

(6-16)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.455 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4231 reflections
a = 17.468 (3) Å	θ = 3.3–27.5°
b = 6.2025 (10) Å	µ = 0.12 mm^−1
c = 16.338 (3) Å	T = 100 K
β = 92.208 (9)°	Irregular, clear light colourless
V = 1768.9 (5) Å^3	0.2 × 0.2 × 0.2 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	4164 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.047
profile data from ω–scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan Blessing 1995	h = −20→20
Tmin = 0.838, Tmax = 1	k = −7→7
9932 measured reflections	l = −15→19
5388 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.087	w = 1/[σ^2(Fo^2) + (0.1622P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.235	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 1.09 e Å^−3
5388 reflections	Δρmin = −0.34 e Å^−3
507 parameters	Absolute structure: Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: −0.3 (7)

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
F1	0.1790 (3)	0.9720 (7)	0.5473 (3)	0.0281 (11)
F2	0.0145 (3)	0.2635 (8)	0.4532 (4)	0.0437 (14)
F3	0.3328 (3)	0.4609 (8)	0.3023 (3)	0.0301 (11)
F4	0.1625 (3)	1.0192 (7)	0.3549 (3)	0.0293 (11)
O1	0.6100 (3)	0.8255 (9)	0.4345 (4)	0.0283 (13)
N1	0.2576 (4)	0.6249 (10)	0.4834 (4)	0.0266 (15)
C1	0.2846 (4)	0.7763 (12)	0.4208 (5)	0.0220 (16)
H1	0.2674	0.9228	0.4379	0.026*
C2	0.2954 (5)	0.4129 (14)	0.4837 (5)	0.0288 (18)
H2A	0.2915	0.3477	0.4284	0.035*
H2B	0.271	0.3145	0.5226	0.035*
C3	0.3791 (4)	0.4502 (14)	0.5097 (5)	0.0277 (18)
H3A	0.3824	0.4847	0.5689	0.033*
H3B	0.4081	0.3152	0.5015	0.033*
C4	0.4962 (5)	0.6459 (12)	0.4645 (5)	0.0252 (17)
H4	0.5269	0.5373	0.4904	0.03*
C5	0.5310 (5)	0.8232 (12)	0.4277 (5)	0.0243 (17)
C6	0.4869 (4)	0.9807 (11)	0.3867 (5)	0.0187 (16)
H6	0.511	1.0994	0.3614	0.022*
C7	0.4068 (4)	0.9614 (13)	0.3834 (5)	0.0219 (16)
H7	0.3761	1.0661	0.3551	0.026*
C8	0.3716 (4)	0.7837 (12)	0.4228 (5)	0.0220 (16)
C9	0.4162 (4)	0.6294 (12)	0.4631 (5)	0.0222 (16)
C10	0.6475 (5)	1.0049 (12)	0.4031 (6)	0.0261 (18)
H10A	0.6402	1.0074	0.3433	0.039*
H10B	0.7023	0.9963	0.4178	0.039*
H10C	0.6262	1.1368	0.4261	0.039*
C11	0.1766 (4)	0.6179 (12)	0.4891 (5)	0.0233 (16)
C12	0.1371 (4)	0.7876 (12)	0.5236 (5)	0.0221 (17)
C13	0.0604 (5)	0.7845 (15)	0.5359 (6)	0.036 (2)
H13	0.0364	0.9056	0.5597	0.043*
C14	0.0178 (5)	0.6060 (15)	0.5140 (6)	0.034 (2)
H14	−0.0354	0.5985	0.5235	0.041*
C15	0.0549 (5)	0.4409 (14)	0.4784 (6)	0.031 (2)
C16	0.1330 (4)	0.4433 (14)	0.4643 (5)	0.0270 (18)
H16	0.1561	0.3249	0.4378	0.032*
C17	0.2495 (5)	0.7393 (13)	0.3357 (5)	0.0256 (17)
C18	0.1878 (4)	0.8650 (12)	0.3062 (5)	0.0256 (17)
C19	0.1501 (5)	0.8393 (13)	0.2319 (5)	0.0288 (19)
H19	0.1093	0.9328	0.2152	0.035*
C20	0.1729 (5)	0.6733 (14)	0.1818 (6)	0.0322 (19)
H20	0.1468	0.6504	0.1304	0.039*
C21	0.2349 (5)	0.5369 (13)	0.2063 (5)	0.0260 (18)
H21	0.2506	0.4211	0.1728	0.031*
C22	0.2707 (5)	0.5798 (13)	0.2801 (5)	0.0281 (18)
F5	0.8237 (3)	0.0267 (8)	0.8186 (3)	0.0340 (12)
F6	0.9853 (3)	0.7391 (8)	0.7345 (4)	0.0464 (15)
F7	0.8384 (3)	−0.0158 (7)	0.6273 (3)	0.0269 (11)
F8	0.6640 (3)	0.5371 (8)	0.5672 (3)	0.0336 (12)
O2	0.3905 (3)	0.1641 (9)	0.6812 (4)	0.0302 (14)
N2	0.7426 (4)	0.3708 (11)	0.7513 (4)	0.0251 (15)
C23	0.7148 (4)	0.2201 (11)	0.6870 (5)	0.0240 (17)
H23	0.7332	0.0739	0.7045	0.029*
C24	0.7065 (5)	0.5832 (13)	0.7494 (5)	0.0307 (19)
H24A	0.7102	0.6502	0.6947	0.037*
H24B	0.7311	0.6795	0.7909	0.037*
C25	0.6208 (5)	0.5416 (14)	0.7692 (5)	0.0301 (19)
H25A	0.6179	0.5098	0.8284	0.036*
H25B	0.5913	0.6753	0.758	0.036*
C26	0.5040 (5)	0.3368 (13)	0.7181 (5)	0.0276 (18)
H26	0.4735	0.4407	0.7445	0.033*
C27	0.4689 (4)	0.1683 (13)	0.6778 (5)	0.0256 (18)
C28	0.5126 (5)	0.0142 (12)	0.6367 (5)	0.0238 (18)
H28	0.4887	−0.1016	0.6075	0.029*
C29	0.5924 (4)	0.0375 (13)	0.6403 (5)	0.0238 (17)
H29	0.6231	−0.0641	0.6131	0.029*
C30	0.6278 (5)	0.2086 (13)	0.6837 (5)	0.0263 (18)
C31	0.5834 (5)	0.3601 (12)	0.7216 (5)	0.0268 (18)
C32	0.3535 (5)	−0.0205 (12)	0.6444 (6)	0.0269 (18)
H32A	0.3596	−0.0172	0.5851	0.04*
H32B	0.2989	−0.0179	0.6559	0.04*
H32C	0.3767	−0.1523	0.6672	0.04*
C33	0.8240 (4)	0.3787 (13)	0.7612 (5)	0.0241 (17)
C34	0.8632 (5)	0.2081 (13)	0.7974 (5)	0.0260 (18)
C35	0.9415 (5)	0.2099 (15)	0.8120 (6)	0.037 (2)
H35	0.9663	0.0868	0.8352	0.045*
C36	0.9843 (5)	0.3903 (15)	0.7929 (6)	0.038 (2)
H36	1.0379	0.3973	0.8052	0.045*
C37	0.9458 (5)	0.5568 (15)	0.7557 (6)	0.035 (2)
C38	0.8673 (5)	0.5571 (14)	0.7395 (5)	0.0289 (18)
H38	0.8432	0.678	0.7138	0.035*
C39	0.7497 (4)	0.2632 (12)	0.6047 (5)	0.0237 (17)
C40	0.8114 (4)	0.1429 (13)	0.5778 (5)	0.0272 (18)
C41	0.8499 (5)	0.1794 (14)	0.5068 (5)	0.0309 (19)
H41	0.8929	0.0946	0.4933	0.037*
C42	0.8235 (5)	0.3441 (14)	0.4563 (6)	0.032 (2)
H42	0.848	0.3716	0.4065	0.039*
C43	0.7611 (5)	0.4712 (13)	0.4776 (5)	0.0259 (18)
H43	0.7439	0.5875	0.4438	0.031*
C44	0.7252 (5)	0.4228 (13)	0.5491 (5)	0.0282 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.026 (2)	0.031 (2)	0.027 (3)	−0.0050 (19)	0.000 (2)	−0.0096 (19)
F2	0.032 (3)	0.037 (3)	0.062 (4)	−0.013 (2)	−0.003 (3)	−0.006 (3)
F3	0.026 (2)	0.043 (3)	0.021 (3)	0.010 (2)	0.0022 (19)	0.004 (2)
F4	0.032 (3)	0.037 (3)	0.018 (3)	0.016 (2)	−0.0068 (19)	−0.0051 (19)
O1	0.021 (3)	0.032 (3)	0.032 (4)	−0.004 (2)	−0.001 (2)	0.003 (2)
N1	0.034 (4)	0.020 (3)	0.025 (4)	−0.002 (3)	−0.002 (3)	0.003 (3)
C1	0.024 (4)	0.021 (4)	0.021 (4)	−0.005 (3)	0.007 (3)	0.002 (3)
C2	0.036 (5)	0.028 (4)	0.022 (5)	0.008 (4)	−0.005 (3)	0.003 (3)
C3	0.024 (4)	0.044 (4)	0.015 (4)	0.001 (4)	0.004 (3)	0.005 (3)
C4	0.029 (4)	0.022 (4)	0.024 (4)	−0.002 (3)	0.000 (3)	0.003 (3)
C5	0.028 (4)	0.025 (4)	0.021 (5)	−0.002 (3)	0.006 (3)	−0.002 (3)
C6	0.023 (4)	0.016 (3)	0.017 (4)	−0.004 (3)	0.003 (3)	0.002 (3)
C7	0.019 (4)	0.029 (4)	0.018 (4)	−0.003 (3)	0.003 (3)	0.000 (3)
C8	0.027 (4)	0.025 (4)	0.014 (4)	−0.001 (3)	0.004 (3)	0.000 (3)
C9	0.025 (4)	0.021 (4)	0.020 (4)	−0.001 (3)	0.005 (3)	−0.004 (3)
C10	0.021 (4)	0.025 (4)	0.032 (5)	−0.003 (3)	0.003 (3)	0.000 (3)
C11	0.026 (4)	0.020 (3)	0.024 (5)	0.000 (3)	−0.002 (3)	0.001 (3)
C12	0.025 (4)	0.022 (4)	0.019 (4)	−0.004 (3)	−0.001 (3)	−0.007 (3)
C13	0.030 (4)	0.041 (5)	0.036 (5)	0.006 (4)	0.005 (4)	0.001 (4)
C14	0.019 (4)	0.044 (5)	0.039 (6)	0.003 (4)	0.006 (4)	0.005 (4)
C15	0.026 (4)	0.038 (5)	0.029 (5)	−0.006 (4)	−0.005 (4)	0.000 (4)
C16	0.022 (4)	0.036 (4)	0.023 (5)	0.002 (3)	−0.001 (3)	0.004 (3)
C17	0.022 (4)	0.026 (4)	0.029 (5)	−0.002 (3)	0.001 (3)	0.002 (3)
C18	0.026 (4)	0.024 (4)	0.026 (5)	0.003 (3)	0.005 (3)	−0.001 (3)
C19	0.026 (4)	0.029 (4)	0.031 (5)	0.000 (3)	0.000 (4)	0.004 (3)
C20	0.033 (4)	0.040 (5)	0.024 (5)	0.000 (4)	−0.001 (4)	0.000 (4)
C21	0.026 (4)	0.036 (4)	0.015 (4)	−0.008 (3)	0.003 (3)	−0.005 (3)
C22	0.031 (4)	0.022 (4)	0.031 (5)	0.005 (3)	0.003 (4)	0.003 (3)
F5	0.033 (3)	0.044 (3)	0.025 (3)	0.005 (2)	−0.004 (2)	0.007 (2)
F6	0.035 (3)	0.037 (3)	0.067 (4)	−0.011 (2)	0.006 (3)	−0.003 (3)
F7	0.028 (2)	0.034 (2)	0.019 (3)	0.0144 (19)	0.0028 (19)	0.0043 (18)
F8	0.028 (3)	0.049 (3)	0.024 (3)	0.010 (2)	0.002 (2)	0.007 (2)
O2	0.023 (3)	0.034 (3)	0.034 (4)	0.000 (2)	0.002 (2)	−0.007 (2)
N2	0.028 (3)	0.029 (4)	0.018 (4)	0.002 (3)	0.002 (3)	−0.001 (3)
C23	0.024 (4)	0.016 (3)	0.031 (5)	−0.001 (3)	−0.005 (3)	0.001 (3)
C24	0.046 (5)	0.020 (4)	0.025 (5)	0.015 (4)	−0.005 (4)	−0.002 (3)
C25	0.029 (4)	0.039 (5)	0.021 (5)	0.004 (4)	−0.006 (3)	−0.003 (4)
C26	0.028 (4)	0.028 (4)	0.027 (5)	0.012 (4)	0.008 (3)	−0.005 (3)
C27	0.021 (4)	0.031 (4)	0.025 (5)	−0.001 (3)	−0.001 (3)	−0.004 (3)
C28	0.027 (4)	0.027 (4)	0.017 (5)	0.007 (3)	−0.005 (3)	−0.007 (3)
C29	0.019 (4)	0.034 (4)	0.018 (4)	0.004 (3)	−0.002 (3)	−0.003 (3)
C30	0.027 (4)	0.026 (4)	0.025 (5)	−0.001 (3)	−0.008 (3)	0.001 (3)
C31	0.029 (4)	0.028 (4)	0.022 (5)	0.004 (4)	−0.001 (3)	−0.002 (3)
C32	0.024 (4)	0.027 (4)	0.030 (5)	−0.009 (3)	−0.002 (4)	−0.005 (3)
C33	0.020 (4)	0.030 (4)	0.022 (4)	0.002 (3)	−0.002 (3)	−0.006 (3)
C34	0.028 (4)	0.026 (4)	0.024 (5)	−0.001 (3)	−0.001 (3)	0.000 (3)
C35	0.036 (5)	0.037 (5)	0.038 (6)	0.012 (4)	−0.006 (4)	−0.002 (4)
C36	0.024 (5)	0.041 (5)	0.048 (6)	0.006 (4)	−0.005 (4)	−0.022 (4)
C37	0.035 (5)	0.039 (5)	0.032 (6)	−0.003 (4)	0.006 (4)	−0.003 (4)
C38	0.033 (4)	0.032 (4)	0.022 (5)	−0.003 (4)	−0.003 (3)	−0.007 (3)
C39	0.023 (4)	0.022 (4)	0.027 (5)	−0.005 (3)	−0.001 (3)	−0.007 (3)
C40	0.023 (4)	0.032 (4)	0.026 (5)	0.006 (3)	−0.006 (3)	0.005 (3)
C41	0.028 (4)	0.040 (5)	0.024 (5)	−0.001 (4)	0.002 (3)	0.000 (4)
C42	0.035 (5)	0.038 (5)	0.025 (5)	0.001 (4)	0.005 (4)	0.008 (4)
C43	0.024 (4)	0.033 (4)	0.020 (5)	−0.002 (3)	−0.002 (3)	0.001 (3)
C44	0.040 (5)	0.024 (4)	0.020 (5)	0.007 (4)	−0.007 (4)	−0.001 (3)

Geometric parameters (Å, º)

F1—C12	1.403 (8)	F5—C34	1.371 (9)
F2—C15	1.362 (10)	F6—C37	1.376 (11)
F3—C22	1.350 (9)	F7—C40	1.348 (9)
F4—C18	1.331 (9)	F8—C44	1.325 (10)
O1—C5	1.381 (10)	O2—C27	1.373 (9)
O1—C10	1.399 (10)	O2—C32	1.436 (9)
N1—C1	1.479 (10)	N2—C23	1.474 (10)
N1—C2	1.472 (10)	N2—C24	1.461 (10)
N1—C11	1.421 (10)	N2—C33	1.425 (10)
C1—H1	1	C23—H23	1
C1—C8	1.520 (10)	C23—C30	1.520 (11)
C1—C17	1.515 (12)	C23—C39	1.521 (12)
C2—H2A	0.99	C24—H24A	0.99
C2—H2B	0.99	C24—H24B	0.99
C2—C3	1.524 (11)	C24—C25	1.565 (13)
C3—H3A	0.99	C25—H25A	0.99
C3—H3B	0.99	C25—H25B	0.99
C3—C9	1.507 (11)	C25—C31	1.503 (11)
C4—H4	0.95	C26—H26	0.95
C4—C5	1.403 (11)	C26—C27	1.368 (11)
C4—C9	1.401 (11)	C26—C31	1.393 (12)
C5—C6	1.399 (11)	C27—C28	1.409 (11)
C6—H6	0.95	C28—H28	0.95
C6—C7	1.405 (11)	C28—C29	1.400 (11)
C7—H7	0.95	C29—H29	0.95
C7—C8	1.427 (11)	C29—C30	1.406 (11)
C8—C9	1.386 (11)	C30—C31	1.379 (12)
C10—H10A	0.98	C32—H32A	0.98
C10—H10B	0.98	C32—H32B	0.98
C10—H10C	0.98	C32—H32C	0.98
C11—C12	1.390 (11)	C33—C34	1.381 (11)
C11—C16	1.376 (12)	C33—C38	1.394 (12)
C12—C13	1.364 (12)	C34—C35	1.379 (12)
C13—H13	0.95	C35—H35	0.95
C13—C14	1.373 (13)	C35—C36	1.388 (14)
C14—H14	0.95	C36—H36	0.95
C14—C15	1.355 (13)	C36—C37	1.363 (13)
C15—C16	1.393 (11)	C37—C38	1.387 (12)
C16—H16	0.95	C38—H38	0.95
C17—C18	1.400 (11)	C39—C40	1.396 (11)
C17—C22	1.403 (12)	C39—C44	1.400 (11)
C18—C19	1.368 (12)	C40—C41	1.382 (13)
C19—H19	0.95	C41—H41	0.95
C19—C20	1.384 (12)	C41—C42	1.382 (12)
C20—H20	0.95	C42—H42	0.95
C20—C21	1.420 (12)	C42—C43	1.400 (12)
C21—H21	0.95	C43—H43	0.95
C21—C22	1.363 (12)	C43—C44	1.380 (13)
C5—O1—C10	117.3 (6)	C27—O2—C32	115.6 (6)
C2—N1—C1	114.5 (7)	C24—N2—C23	115.2 (6)
C11—N1—C1	114.1 (6)	C33—N2—C23	113.8 (6)
C11—N1—C2	114.9 (6)	C33—N2—C24	113.6 (7)
N1—C1—H1	106.1	N2—C23—H23	106.1
N1—C1—C8	110.5 (6)	N2—C23—C30	110.9 (6)
N1—C1—C17	114.2 (6)	N2—C23—C39	112.7 (6)
C8—C1—H1	106.1	C30—C23—H23	106.1
C17—C1—H1	106.1	C30—C23—C39	114.2 (7)
C17—C1—C8	113.1 (6)	C39—C23—H23	106.1
N1—C2—H2A	110.3	N2—C24—H24A	110.7
N1—C2—H2B	110.3	N2—C24—H24B	110.7
N1—C2—C3	106.9 (7)	N2—C24—C25	105.3 (7)
H2A—C2—H2B	108.6	H24A—C24—H24B	108.8
C3—C2—H2A	110.3	C25—C24—H24A	110.7
C3—C2—H2B	110.3	C25—C24—H24B	110.7
C2—C3—H3A	108.9	C24—C25—H25A	108.6
C2—C3—H3B	108.9	C24—C25—H25B	108.6
H3A—C3—H3B	107.7	H25A—C25—H25B	107.6
C9—C3—C2	113.4 (7)	C31—C25—C24	114.6 (7)
C9—C3—H3A	108.9	C31—C25—H25A	108.6
C9—C3—H3B	108.9	C31—C25—H25B	108.6
C5—C4—H4	120	C27—C26—H26	119.2
C9—C4—H4	120	C27—C26—C31	121.7 (7)
C9—C4—C5	119.9 (7)	C31—C26—H26	119.2
O1—C5—C4	114.9 (7)	O2—C27—C28	124.5 (7)
O1—C5—C6	124.1 (7)	C26—C27—O2	115.1 (7)
C6—C5—C4	120.9 (7)	C26—C27—C28	120.4 (7)
C5—C6—H6	120.4	C27—C28—H28	121.1
C5—C6—C7	119.2 (7)	C29—C28—C27	117.8 (7)
C7—C6—H6	120.4	C29—C28—H28	121.1
C6—C7—H7	120.2	C28—C29—H29	119.4
C6—C7—C8	119.7 (7)	C28—C29—C30	121.1 (7)
C8—C7—H7	120.2	C30—C29—H29	119.4
C7—C8—C1	117.5 (7)	C29—C30—C23	118.2 (7)
C9—C8—C1	122.2 (7)	C31—C30—C23	122.0 (7)
C9—C8—C7	120.3 (7)	C31—C30—C29	119.8 (7)
C4—C9—C3	119.6 (7)	C26—C31—C25	120.7 (7)
C8—C9—C3	120.3 (7)	C30—C31—C25	120.2 (7)
C8—C9—C4	120.0 (7)	C30—C31—C26	119.1 (7)
O1—C10—H10A	109.5	O2—C32—H32A	109.5
O1—C10—H10B	109.5	O2—C32—H32B	109.5
O1—C10—H10C	109.5	O2—C32—H32C	109.5
H10A—C10—H10B	109.5	H32A—C32—H32B	109.5
H10A—C10—H10C	109.5	H32A—C32—H32C	109.5
H10B—C10—H10C	109.5	H32B—C32—H32C	109.5
C12—C11—N1	120.9 (7)	C34—C33—N2	119.9 (7)
C16—C11—N1	123.1 (7)	C34—C33—C38	116.8 (7)
C16—C11—C12	115.9 (7)	C38—C33—N2	123.1 (7)
C11—C12—F1	117.9 (7)	F5—C34—C33	119.4 (7)
C13—C12—F1	118.3 (7)	F5—C34—C35	117.9 (7)
C13—C12—C11	123.8 (8)	C35—C34—C33	122.7 (8)
C12—C13—H13	120.1	C34—C35—H35	119.8
C12—C13—C14	119.9 (8)	C34—C35—C36	120.5 (8)
C14—C13—H13	120.1	C36—C35—H35	119.8
C13—C14—H14	121.3	C35—C36—H36	121.6
C15—C14—C13	117.3 (8)	C37—C36—C35	116.7 (8)
C15—C14—H14	121.3	C37—C36—H36	121.6
F2—C15—C16	117.3 (8)	F6—C37—C38	116.9 (8)
C14—C15—F2	119.3 (7)	C36—C37—F6	119.4 (8)
C14—C15—C16	123.4 (8)	C36—C37—C38	123.6 (9)
C11—C16—C15	119.7 (8)	C33—C38—H38	120.2
C11—C16—H16	120.2	C37—C38—C33	119.5 (8)
C15—C16—H16	120.2	C37—C38—H38	120.2
C18—C17—C1	120.7 (7)	C40—C39—C23	121.7 (7)
C18—C17—C22	112.8 (7)	C40—C39—C44	113.2 (8)
C22—C17—C1	126.4 (7)	C44—C39—C23	125.1 (7)
F4—C18—C17	117.6 (7)	F7—C40—C39	117.2 (7)
F4—C18—C19	117.0 (7)	F7—C40—C41	116.9 (7)
C19—C18—C17	125.4 (7)	C41—C40—C39	125.8 (7)
C18—C19—H19	120.9	C40—C41—H41	121.3
C18—C19—C20	118.2 (7)	C42—C41—C40	117.4 (8)
C20—C19—H19	120.9	C42—C41—H41	121.3
C19—C20—H20	119.7	C41—C42—H42	119.5
C19—C20—C21	120.7 (8)	C41—C42—C43	120.9 (8)
C21—C20—H20	119.7	C43—C42—H42	119.5
C20—C21—H21	121.5	C42—C43—H43	120.9
C22—C21—C20	116.9 (8)	C44—C43—C42	118.1 (7)
C22—C21—H21	121.5	C44—C43—H43	120.9
F3—C22—C17	116.2 (7)	F8—C44—C39	117.5 (8)
F3—C22—C21	117.9 (7)	F8—C44—C43	118.0 (7)
C21—C22—C17	125.9 (8)	C43—C44—C39	124.4 (8)
F1—C12—C13—C14	−179.5 (8)	F5—C34—C35—C36	−179.1 (8)
F2—C15—C16—C11	−179.5 (7)	F6—C37—C38—C33	−178.7 (7)
F4—C18—C19—C20	−176.9 (7)	F7—C40—C41—C42	−178.9 (7)
O1—C5—C6—C7	179.8 (7)	O2—C27—C28—C29	−178.6 (7)
N1—C1—C8—C7	−163.0 (7)	N2—C23—C30—C29	−165.1 (7)
N1—C1—C8—C9	14.9 (10)	N2—C23—C30—C31	15.0 (10)
N1—C1—C17—C18	98.9 (9)	N2—C23—C39—C40	99.0 (8)
N1—C1—C17—C22	−78.6 (10)	N2—C23—C39—C44	−80.6 (9)
N1—C2—C3—C9	−49.1 (9)	N2—C24—C25—C31	−47.2 (9)
N1—C11—C12—F1	4.5 (11)	N2—C33—C34—F5	4.3 (11)
N1—C11—C12—C13	−175.3 (8)	N2—C33—C34—C35	−177.2 (8)
N1—C11—C16—C15	174.4 (8)	N2—C33—C38—C37	176.2 (8)
C1—N1—C2—C3	66.2 (8)	C23—N2—C24—C25	65.5 (9)
C1—N1—C11—C12	−72.6 (9)	C23—N2—C33—C34	−72.6 (9)
C1—N1—C11—C16	110.0 (9)	C23—N2—C33—C38	110.6 (8)
C1—C8—C9—C3	−2.1 (11)	C23—C30—C31—C25	−1.0 (12)
C1—C8—C9—C4	−178.7 (7)	C23—C30—C31—C26	−178.2 (7)
C1—C17—C18—F4	1.2 (11)	C23—C39—C40—F7	0.9 (11)
C1—C17—C18—C19	−177.2 (8)	C23—C39—C40—C41	−175.4 (8)
C1—C17—C22—F3	−6.3 (12)	C23—C39—C44—F8	−4.2 (11)
C1—C17—C22—C21	174.5 (8)	C23—C39—C44—C43	174.7 (7)
C2—N1—C1—C8	−48.3 (9)	C24—N2—C23—C30	−50.1 (9)
C2—N1—C1—C17	80.5 (8)	C24—N2—C23—C39	79.4 (9)
C2—N1—C11—C12	152.3 (7)	C24—N2—C33—C34	152.9 (8)
C2—N1—C11—C16	−25.1 (11)	C24—N2—C33—C38	−23.9 (11)
C2—C3—C9—C4	−163.5 (7)	C24—C25—C31—C26	−164.9 (8)
C2—C3—C9—C8	19.9 (11)	C24—C25—C31—C30	18.0 (11)
C4—C5—C6—C7	0.7 (11)	C26—C27—C28—C29	1.4 (12)
C5—C4—C9—C3	−174.2 (8)	C27—C26—C31—C25	−177.4 (8)
C5—C4—C9—C8	2.4 (11)	C27—C26—C31—C30	−0.3 (13)
C5—C6—C7—C8	0.9 (11)	C27—C28—C29—C30	0.1 (12)
C6—C7—C8—C1	177.1 (7)	C28—C29—C30—C23	178.3 (7)
C6—C7—C8—C9	−0.8 (11)	C28—C29—C30—C31	−1.8 (12)
C7—C8—C9—C3	175.8 (7)	C29—C30—C31—C25	179.0 (8)
C7—C8—C9—C4	−0.8 (11)	C29—C30—C31—C26	1.8 (12)
C8—C1—C17—C18	−133.6 (8)	C30—C23—C39—C40	−133.2 (7)
C8—C1—C17—C22	48.9 (10)	C30—C23—C39—C44	47.2 (10)
C9—C4—C5—O1	178.5 (7)	C31—C26—C27—O2	178.6 (7)
C9—C4—C5—C6	−2.4 (12)	C31—C26—C27—C28	−1.4 (13)
C10—O1—C5—C4	−176.3 (7)	C32—O2—C27—C26	−175.5 (7)
C10—O1—C5—C6	4.6 (11)	C32—O2—C27—C28	4.5 (11)
C11—N1—C1—C8	176.4 (6)	C33—N2—C23—C30	176.2 (6)
C11—N1—C1—C17	−54.7 (9)	C33—N2—C23—C39	−54.3 (9)
C11—N1—C2—C3	−159.0 (7)	C33—N2—C24—C25	−160.7 (6)
C11—C12—C13—C14	0.2 (13)	C33—C34—C35—C36	2.3 (14)
C12—C11—C16—C15	−3.1 (12)	C34—C33—C38—C37	−0.8 (12)
C12—C13—C14—C15	−1.8 (13)	C34—C35—C36—C37	−3.4 (14)
C13—C14—C15—F2	−177.9 (8)	C35—C36—C37—F6	−179.3 (8)
C13—C14—C15—C16	1.0 (14)	C35—C36—C37—C38	2.6 (14)
C14—C15—C16—C11	1.6 (13)	C36—C37—C38—C33	−0.5 (14)
C16—C11—C12—F1	−178.0 (7)	C38—C33—C34—F5	−178.7 (7)
C16—C11—C12—C13	2.3 (12)	C38—C33—C34—C35	−0.1 (12)
C17—C1—C8—C7	67.5 (9)	C39—C23—C30—C29	66.3 (9)
C17—C1—C8—C9	−114.6 (8)	C39—C23—C30—C31	−113.7 (8)
C17—C18—C19—C20	1.4 (13)	C39—C40—C41—C42	−2.6 (13)
C18—C17—C22—F3	176.0 (7)	C40—C39—C44—F8	176.2 (7)
C18—C17—C22—C21	−3.2 (12)	C40—C39—C44—C43	−4.9 (11)
C18—C19—C20—C21	−1.3 (13)	C40—C41—C42—C43	1.3 (12)
C19—C20—C21—C22	−0.9 (12)	C41—C42—C43—C44	−2.1 (12)
C20—C21—C22—F3	−175.9 (7)	C42—C43—C44—F8	−177.0 (7)
C20—C21—C22—C17	3.4 (13)	C42—C43—C44—C39	4.1 (12)
C22—C17—C18—F4	179.0 (7)	C44—C39—C40—F7	−179.5 (7)
C22—C17—C18—C19	0.7 (12)	C44—C39—C40—C41	4.2 (12)

(6-19)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 3693 reflections
a = 18.194 (6) Å	θ = 3.1–27.5°
b = 6.147 (2) Å	µ = 0.12 mm^−1
c = 16.182 (5) Å	T = 100 K
β = 104.903 (11)°	Block, clear light colourless
V = 1749.0 (10) Å^3	0.3 × 0.3 × 0.2 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2613 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.066
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −23→23
Tmin = 0.779, Tmax = 1	k = −6→7
11916 measured reflections	l = −20→21
3963 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.192	w = 1/[σ^2(Fo^2) + (0.0973P)^2 + 0.0745P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3963 reflections	Δρmax = 0.38 e Å^−3
254 parameters	Δρmin = −0.38 e Å^−3

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
F1	0.86240 (8)	0.1093 (2)	0.70468 (10)	0.0348 (4)
F2	0.80120 (8)	0.7590 (2)	0.54908 (10)	0.0320 (4)
F3	0.85387 (8)	0.7235 (3)	0.77573 (9)	0.0323 (4)
F4	0.93400 (9)	0.5665 (3)	0.92468 (10)	0.0387 (4)
O1	0.39732 (10)	0.4549 (3)	0.62654 (11)	0.0300 (4)
N1	0.74705 (11)	0.4056 (3)	0.61550 (13)	0.0241 (5)
C1	0.71641 (13)	0.5372 (4)	0.67590 (15)	0.0232 (5)
H1	0.7293	0.6898	0.6692	0.028*
C2	0.71701 (14)	0.1834 (4)	0.60521 (17)	0.0266 (6)
H2A	0.7246	0.1146	0.6607	0.032*
H2B	0.7436	0.0984	0.5714	0.032*
C3	0.63251 (14)	0.1925 (4)	0.56059 (17)	0.0277 (6)
H3A	0.626	0.2356	0.5015	0.033*
H3B	0.6105	0.0489	0.561	0.033*
C4	0.51260 (14)	0.3291 (4)	0.59238 (15)	0.0254 (5)
H4	0.4866	0.2171	0.5585	0.031*
C5	0.47342 (14)	0.4717 (4)	0.63086 (15)	0.0268 (6)
C6	0.51182 (14)	0.6458 (4)	0.67812 (16)	0.0280 (6)
H6	0.4852	0.7476	0.7016	0.034*
C7	0.58926 (14)	0.6670 (4)	0.69000 (16)	0.0269 (6)
H7	0.6146	0.782	0.7225	0.032*
C8	0.63044 (14)	0.5184 (4)	0.65400 (15)	0.0238 (5)
C9	0.59135 (14)	0.3510 (4)	0.60373 (15)	0.0246 (5)
C10	0.35839 (15)	0.2657 (5)	0.58406 (18)	0.0333 (6)
H10A	0.3561	0.2728	0.5242	0.05*
H10B	0.3077	0.2613	0.5914	0.05*
H10C	0.3854	0.137	0.6082	0.05*
C11	0.82646 (14)	0.4300 (4)	0.62472 (15)	0.0232 (5)
C12	0.85332 (14)	0.6101 (4)	0.58914 (15)	0.0262 (6)
C13	0.92856 (15)	0.6460 (5)	0.59233 (16)	0.0294 (6)
H13	0.9435	0.7703	0.5682	0.035*
C14	0.98156 (15)	0.4923 (5)	0.63241 (16)	0.0308 (6)
H14	1.0327	0.5122	0.6345	0.037*
C15	0.95900 (14)	0.3097 (4)	0.66929 (16)	0.0301 (6)
H15	0.9943	0.2057	0.696	0.036*
C16	0.88288 (14)	0.2858 (4)	0.66537 (16)	0.0262 (6)
C17	0.75366 (14)	0.4698 (4)	0.76840 (15)	0.0246 (5)
C18	0.82381 (15)	0.5587 (4)	0.81095 (16)	0.0267 (6)
C19	0.86490 (14)	0.4797 (5)	0.88938 (16)	0.0296 (6)
C20	0.83710 (15)	0.3171 (5)	0.92968 (17)	0.0326 (6)
H20	0.8652	0.2634	0.982	0.039*
C21	0.76588 (15)	0.2335 (5)	0.89078 (17)	0.0320 (6)
H21	0.7452	0.1258	0.9184	0.038*
C22	0.72489 (14)	0.3077 (4)	0.81143 (16)	0.0274 (6)
H22	0.6774	0.2482	0.7865	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0354 (9)	0.0274 (9)	0.0390 (9)	0.0023 (6)	0.0050 (7)	0.0119 (7)
F2	0.0341 (8)	0.0248 (9)	0.0353 (9)	0.0048 (6)	0.0059 (7)	0.0083 (6)
F3	0.0388 (9)	0.0296 (9)	0.0275 (8)	−0.0087 (6)	0.0067 (7)	0.0032 (6)
F4	0.0338 (9)	0.0497 (11)	0.0289 (8)	−0.0137 (7)	0.0015 (7)	0.0006 (7)
O1	0.0252 (9)	0.0301 (11)	0.0340 (10)	0.0026 (7)	0.0062 (8)	−0.0013 (8)
N1	0.0266 (10)	0.0204 (11)	0.0257 (11)	0.0023 (8)	0.0075 (9)	−0.0008 (8)
C1	0.0284 (12)	0.0177 (13)	0.0222 (12)	0.0029 (9)	0.0041 (10)	0.0007 (9)
C2	0.0280 (12)	0.0223 (14)	0.0295 (13)	0.0011 (10)	0.0073 (10)	−0.0025 (10)
C3	0.0306 (13)	0.0230 (14)	0.0299 (13)	0.0028 (10)	0.0083 (11)	−0.0023 (10)
C4	0.0304 (13)	0.0237 (14)	0.0207 (11)	−0.0014 (10)	0.0039 (10)	−0.0022 (10)
C5	0.0272 (12)	0.0293 (15)	0.0227 (12)	0.0034 (10)	0.0044 (10)	0.0051 (10)
C6	0.0312 (13)	0.0245 (14)	0.0270 (13)	0.0067 (10)	0.0051 (11)	−0.0009 (10)
C7	0.0307 (13)	0.0233 (14)	0.0249 (12)	0.0017 (10)	0.0039 (10)	−0.0002 (10)
C8	0.0281 (12)	0.0227 (13)	0.0202 (11)	0.0022 (10)	0.0055 (10)	0.0031 (9)
C9	0.0277 (12)	0.0241 (14)	0.0217 (12)	0.0028 (10)	0.0056 (10)	0.0012 (10)
C10	0.0275 (13)	0.0346 (16)	0.0354 (15)	0.0003 (11)	0.0035 (11)	−0.0022 (12)
C11	0.0276 (12)	0.0207 (13)	0.0200 (11)	0.0016 (10)	0.0041 (10)	−0.0031 (9)
C12	0.0312 (13)	0.0240 (14)	0.0215 (12)	0.0052 (10)	0.0035 (10)	−0.0002 (10)
C13	0.0328 (13)	0.0320 (15)	0.0239 (12)	−0.0006 (11)	0.0080 (11)	0.0000 (11)
C14	0.0295 (13)	0.0365 (17)	0.0261 (13)	0.0008 (11)	0.0068 (11)	0.0007 (11)
C15	0.0295 (13)	0.0327 (15)	0.0251 (13)	0.0076 (11)	0.0017 (11)	0.0020 (11)
C16	0.0310 (13)	0.0247 (14)	0.0226 (12)	0.0007 (10)	0.0060 (10)	0.0026 (10)
C17	0.0302 (12)	0.0213 (13)	0.0211 (12)	0.0016 (10)	0.0044 (10)	−0.0011 (9)
C18	0.0344 (14)	0.0240 (14)	0.0239 (12)	−0.0032 (10)	0.0116 (11)	−0.0014 (10)
C19	0.0257 (12)	0.0355 (16)	0.0253 (13)	−0.0035 (11)	0.0026 (10)	−0.0042 (11)
C20	0.0368 (14)	0.0370 (17)	0.0229 (13)	−0.0044 (12)	0.0058 (11)	0.0042 (11)
C21	0.0392 (15)	0.0292 (16)	0.0288 (14)	−0.0038 (11)	0.0107 (12)	0.0033 (11)
C22	0.0301 (13)	0.0249 (14)	0.0265 (13)	−0.0043 (10)	0.0059 (10)	−0.0004 (10)

Geometric parameters (Å, º)

F1—C16	1.358 (3)	C7—H7	0.93
F2—C12	1.357 (3)	C7—C8	1.400 (3)
F3—C18	1.345 (3)	C8—C9	1.389 (4)
F4—C19	1.350 (3)	C10—H10A	0.96
O1—C5	1.372 (3)	C10—H10B	0.96
O1—C10	1.441 (3)	C10—H10C	0.96
N1—C1	1.483 (3)	C11—C12	1.393 (4)
N1—C2	1.465 (3)	C11—C16	1.387 (3)
N1—C11	1.422 (3)	C12—C13	1.374 (4)
C1—H1	0.98	C13—H13	0.93
C1—C8	1.517 (3)	C13—C14	1.386 (4)
C1—C17	1.533 (3)	C14—H14	0.93
C2—H2A	0.97	C14—C15	1.382 (4)
C2—H2B	0.97	C15—H15	0.93
C2—C3	1.522 (3)	C15—C16	1.378 (4)
C3—H3A	0.97	C17—C18	1.396 (3)
C3—H3B	0.97	C17—C22	1.393 (4)
C3—C9	1.505 (3)	C18—C19	1.385 (4)
C4—H4	0.93	C19—C20	1.360 (4)
C4—C5	1.376 (4)	C20—H20	0.93
C4—C9	1.403 (3)	C20—C21	1.386 (4)
C5—C6	1.394 (4)	C21—H21	0.93
C6—H6	0.93	C21—C22	1.386 (4)
C6—C7	1.378 (4)	C22—H22	0.93
C5—O1—C10	116.8 (2)	O1—C10—H10B	109.5
C2—N1—C1	113.01 (19)	O1—C10—H10C	109.5
C11—N1—C1	114.68 (19)	H10A—C10—H10B	109.5
C11—N1—C2	116.70 (19)	H10A—C10—H10C	109.5
N1—C1—H1	108	H10B—C10—H10C	109.5
N1—C1—C8	110.15 (19)	C12—C11—N1	119.7 (2)
N1—C1—C17	110.45 (19)	C16—C11—N1	126.2 (2)
C8—C1—H1	108	C16—C11—C12	114.1 (2)
C8—C1—C17	112.2 (2)	F2—C12—C11	117.2 (2)
C17—C1—H1	108	F2—C12—C13	118.4 (2)
N1—C2—H2A	109.9	C13—C12—C11	124.3 (2)
N1—C2—H2B	109.9	C12—C13—H13	120.8
N1—C2—C3	108.7 (2)	C12—C13—C14	118.3 (3)
H2A—C2—H2B	108.3	C14—C13—H13	120.8
C3—C2—H2A	109.9	C13—C14—H14	119.8
C3—C2—H2B	109.9	C15—C14—C13	120.5 (2)
C2—C3—H3A	109.3	C15—C14—H14	119.8
C2—C3—H3B	109.3	C14—C15—H15	120.9
H3A—C3—H3B	108	C16—C15—C14	118.2 (2)
C9—C3—C2	111.5 (2)	C16—C15—H15	120.9
C9—C3—H3A	109.3	F1—C16—C11	118.3 (2)
C9—C3—H3B	109.3	F1—C16—C15	117.2 (2)
C5—C4—H4	119.7	C15—C16—C11	124.5 (2)
C5—C4—C9	120.7 (2)	C18—C17—C1	119.6 (2)
C9—C4—H4	119.7	C22—C17—C1	123.6 (2)
O1—C5—C4	124.2 (2)	C22—C17—C18	116.6 (2)
O1—C5—C6	116.3 (2)	F3—C18—C17	120.4 (2)
C4—C5—C6	119.5 (2)	F3—C18—C19	118.0 (2)
C5—C6—H6	120	C19—C18—C17	121.6 (2)
C7—C6—C5	119.9 (2)	F4—C19—C18	118.3 (2)
C7—C6—H6	120	F4—C19—C20	120.6 (2)
C6—C7—H7	119.4	C20—C19—C18	121.2 (2)
C6—C7—C8	121.2 (2)	C19—C20—H20	120.8
C8—C7—H7	119.4	C19—C20—C21	118.3 (2)
C7—C8—C1	118.9 (2)	C21—C20—H20	120.8
C9—C8—C1	122.3 (2)	C20—C21—H21	119.5
C9—C8—C7	118.6 (2)	C20—C21—C22	121.1 (3)
C4—C9—C3	119.4 (2)	C22—C21—H21	119.5
C8—C9—C3	120.7 (2)	C17—C22—H22	119.4
C8—C9—C4	119.9 (2)	C21—C22—C17	121.1 (2)
O1—C10—H10A	109.5	C21—C22—H22	119.4
F2—C12—C13—C14	−179.2 (2)	C6—C7—C8—C1	−174.4 (2)
F3—C18—C19—F4	−2.4 (4)	C6—C7—C8—C9	1.7 (4)
F3—C18—C19—C20	178.3 (2)	C7—C8—C9—C3	177.4 (2)
F4—C19—C20—C21	180.0 (2)	C7—C8—C9—C4	−2.2 (4)
O1—C5—C6—C7	176.1 (2)	C8—C1—C17—C18	−152.7 (2)
N1—C1—C8—C7	−165.5 (2)	C8—C1—C17—C22	33.4 (3)
N1—C1—C8—C9	18.6 (3)	C9—C4—C5—O1	−176.5 (2)
N1—C1—C17—C18	84.0 (3)	C9—C4—C5—C6	3.2 (4)
N1—C1—C17—C22	−90.0 (3)	C10—O1—C5—C4	4.8 (3)
N1—C2—C3—C9	−50.7 (3)	C10—O1—C5—C6	−174.9 (2)
N1—C11—C12—F2	2.0 (3)	C11—N1—C1—C8	173.67 (19)
N1—C11—C12—C13	−178.1 (2)	C11—N1—C1—C17	−61.8 (3)
N1—C11—C16—F1	−3.9 (4)	C11—N1—C2—C3	−156.6 (2)
N1—C11—C16—C15	176.6 (2)	C11—C12—C13—C14	0.9 (4)
C1—N1—C2—C3	67.2 (3)	C12—C11—C16—F1	177.6 (2)
C1—N1—C11—C12	−80.0 (3)	C12—C11—C16—C15	−1.9 (4)
C1—N1—C11—C16	101.6 (3)	C12—C13—C14—C15	−1.0 (4)
C1—C8—C9—C3	−6.6 (4)	C13—C14—C15—C16	−0.3 (4)
C1—C8—C9—C4	173.7 (2)	C14—C15—C16—F1	−177.7 (2)
C1—C17—C18—F3	8.9 (4)	C14—C15—C16—C11	1.9 (4)
C1—C17—C18—C19	−170.2 (2)	C16—C11—C12—F2	−179.4 (2)
C1—C17—C22—C21	171.5 (2)	C16—C11—C12—C13	0.5 (4)
C2—N1—C1—C8	−49.2 (3)	C17—C1—C8—C7	71.0 (3)
C2—N1—C1—C17	75.3 (3)	C17—C1—C8—C9	−104.9 (3)
C2—N1—C11—C12	144.5 (2)	C17—C18—C19—F4	176.7 (2)
C2—N1—C11—C16	−33.9 (3)	C17—C18—C19—C20	−2.5 (4)
C2—C3—C9—C4	−157.9 (2)	C18—C17—C22—C21	−2.7 (4)
C2—C3—C9—C8	22.4 (3)	C18—C19—C20—C21	−0.8 (4)
C4—C5—C6—C7	−3.7 (4)	C19—C20—C21—C22	2.2 (4)
C5—C4—C9—C3	−179.9 (2)	C20—C21—C22—C17	−0.4 (4)
C5—C4—C9—C8	−0.2 (4)	C22—C17—C18—F3	−176.7 (2)
C5—C6—C7—C8	1.2 (4)	C22—C17—C18—C19	4.2 (4)

(6-21)

Crystal data

C22H17F4NO	F(000) = 400
Mr = 387.36	Dx = 1.455 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 2379 reflections
a = 7.6714 (11) Å	θ = 3.1–27.5°
b = 7.1287 (9) Å	µ = 0.12 mm^−1
c = 16.428 (2) Å	T = 100 K
β = 100.298 (6)°	Block, clear light colourless
V = 883.9 (2) Å^3	0.2 × 0.2 × 0.1 mm
Z = 2

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2379 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.034
profile data from ω–scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −9→9
Tmin = 0.868, Tmax = 1	k = −8→8
4823 measured reflections	l = −19→19
2621 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.1042P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.19 e Å^−3
2621 reflections	Δρmin = −0.18 e Å^−3
254 parameters	Absolute structure: Flack x determined using 843 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: −0.5 (6)

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
F3	0.5886 (3)	0.8393 (3)	0.58570 (13)	0.0293 (5)
F1	0.2248 (3)	0.7416 (3)	0.38794 (13)	0.0314 (6)
F2	0.3071 (3)	0.4291 (3)	0.64399 (14)	0.0363 (6)
F4	0.8992 (3)	0.2142 (3)	0.73338 (13)	0.0388 (6)
O1	0.9452 (4)	0.0709 (4)	0.28952 (16)	0.0311 (7)
N1	0.3809 (4)	0.4506 (4)	0.47872 (18)	0.0222 (7)
C5	0.8430 (5)	0.1682 (5)	0.3351 (2)	0.0229 (8)
C11	0.2725 (5)	0.5778 (5)	0.5142 (2)	0.0222 (8)
C9	0.5941 (5)	0.2123 (5)	0.4051 (2)	0.0205 (8)
C8	0.6589 (5)	0.3877 (5)	0.43162 (19)	0.0193 (8)
C4	0.6877 (5)	0.1034 (5)	0.3563 (2)	0.0244 (8)
H4	0.6436	−0.0165	0.3376	0.029*
C17	0.6640 (5)	0.5202 (5)	0.5748 (2)	0.0215 (8)
C16	0.2345 (5)	0.5713 (5)	0.5935 (2)	0.0263 (9)
C19	0.7330 (5)	0.6867 (5)	0.7056 (2)	0.0253 (9)
H19	0.7277	0.7996	0.7358	0.03*
C21	0.8178 (6)	0.3712 (5)	0.6968 (2)	0.0277 (9)
C18	0.6624 (5)	0.6792 (5)	0.6225 (2)	0.0235 (8)
C1	0.5657 (5)	0.5128 (5)	0.4846 (2)	0.0208 (8)
H1	0.5636	0.6427	0.4615	0.025*
C22	0.7476 (5)	0.3634 (5)	0.6137 (2)	0.0235 (8)
H22	0.7563	0.2515	0.5833	0.028*
C13	0.0889 (5)	0.8596 (5)	0.4945 (3)	0.0293 (9)
H13	0.0388	0.9595	0.4597	0.035*
C12	0.1954 (5)	0.7272 (5)	0.4667 (2)	0.0231 (8)
C7	0.8167 (5)	0.4512 (5)	0.4100 (2)	0.0240 (8)
H7	0.8612	0.5711	0.4286	0.029*
C20	0.8116 (5)	0.5286 (5)	0.7446 (2)	0.0274 (9)
H20	0.8593	0.5285	0.8021	0.033*
C2	0.3651 (5)	0.2503 (5)	0.4962 (2)	0.0226 (8)
H2A	0.2408	0.2192	0.4995	0.027*
H2B	0.4405	0.2184	0.5498	0.027*
C6	0.9093 (5)	0.3445 (5)	0.3626 (2)	0.0268 (9)
H6	1.0167	0.3897	0.3487	0.032*
C3	0.4238 (5)	0.1402 (5)	0.4270 (2)	0.0236 (8)
H3A	0.4397	0.0071	0.4439	0.028*
H3B	0.3295	0.1459	0.3774	0.028*
C15	0.1296 (5)	0.6977 (5)	0.6249 (3)	0.0318 (9)
H15	0.1072	0.686	0.6797	0.038*
C10	0.8790 (6)	−0.1046 (5)	0.2545 (2)	0.0326 (10)
H10A	0.7654	−0.0844	0.2174	0.049*
H10B	0.8621	−0.1908	0.2989	0.049*
H10C	0.9641	−0.1587	0.2232	0.049*
C14	0.0572 (5)	0.8429 (5)	0.5741 (3)	0.0311 (9)
H14	−0.0156	0.9329	0.5945	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F3	0.0321 (13)	0.0254 (11)	0.0290 (11)	0.0019 (10)	0.0018 (10)	−0.0008 (9)
F1	0.0401 (14)	0.0267 (11)	0.0253 (11)	0.0011 (11)	0.0000 (10)	0.0038 (9)
F2	0.0427 (15)	0.0380 (13)	0.0310 (12)	0.0105 (12)	0.0137 (11)	0.0111 (11)
F4	0.0429 (16)	0.0392 (13)	0.0313 (13)	0.0149 (12)	−0.0017 (11)	0.0080 (11)
O1	0.0315 (17)	0.0289 (14)	0.0348 (15)	−0.0045 (13)	0.0110 (13)	−0.0112 (12)
N1	0.0194 (17)	0.0214 (15)	0.0261 (16)	−0.0018 (13)	0.0045 (13)	0.0021 (12)
C5	0.025 (2)	0.0236 (19)	0.0204 (18)	0.0009 (16)	0.0050 (16)	−0.0021 (15)
C11	0.0183 (19)	0.0207 (18)	0.0269 (18)	−0.0034 (15)	0.0022 (15)	0.0014 (15)
C9	0.020 (2)	0.0227 (19)	0.0167 (17)	−0.0015 (16)	−0.0016 (14)	0.0038 (14)
C8	0.0180 (19)	0.0221 (19)	0.0165 (17)	−0.0010 (16)	−0.0008 (14)	0.0012 (14)
C4	0.028 (2)	0.0208 (18)	0.0224 (18)	−0.0050 (17)	0.0003 (16)	−0.0010 (15)
C17	0.0158 (18)	0.0265 (19)	0.0221 (18)	−0.0023 (16)	0.0030 (15)	−0.0027 (15)
C16	0.025 (2)	0.0237 (18)	0.029 (2)	−0.0034 (17)	0.0009 (17)	0.0054 (16)
C19	0.023 (2)	0.031 (2)	0.0230 (19)	−0.0007 (17)	0.0067 (16)	−0.0050 (16)
C21	0.025 (2)	0.030 (2)	0.027 (2)	0.0038 (18)	0.0017 (16)	0.0081 (16)
C18	0.021 (2)	0.0213 (18)	0.0280 (19)	0.0031 (16)	0.0044 (16)	0.0023 (16)
C1	0.0181 (19)	0.0212 (17)	0.0235 (19)	0.0006 (16)	0.0044 (15)	0.0023 (15)
C22	0.022 (2)	0.0240 (19)	0.0237 (18)	0.0023 (17)	0.0004 (15)	−0.0035 (15)
C13	0.022 (2)	0.0196 (19)	0.042 (2)	−0.0015 (17)	−0.0055 (17)	0.0038 (17)
C12	0.021 (2)	0.0226 (19)	0.024 (2)	−0.0065 (17)	−0.0009 (15)	−0.0012 (16)
C7	0.025 (2)	0.0217 (19)	0.0249 (18)	−0.0069 (17)	0.0031 (16)	−0.0035 (15)
C20	0.024 (2)	0.039 (2)	0.0194 (18)	0.0000 (18)	0.0032 (16)	0.0009 (17)
C2	0.023 (2)	0.0185 (19)	0.0265 (18)	−0.0052 (16)	0.0041 (16)	0.0034 (15)
C6	0.024 (2)	0.030 (2)	0.028 (2)	−0.0055 (17)	0.0077 (17)	−0.0010 (16)
C3	0.023 (2)	0.0212 (18)	0.0258 (19)	−0.0041 (16)	0.0002 (16)	0.0008 (15)
C15	0.031 (2)	0.031 (2)	0.037 (2)	−0.0045 (19)	0.0166 (18)	−0.0037 (19)
C10	0.038 (3)	0.026 (2)	0.035 (2)	−0.0011 (19)	0.008 (2)	−0.0104 (17)
C14	0.023 (2)	0.0234 (19)	0.048 (2)	−0.0005 (18)	0.0089 (19)	−0.0048 (19)

Geometric parameters (Å, º)

F3—C18	1.366 (4)	C19—C18	1.378 (5)
F1—C12	1.357 (4)	C19—C20	1.381 (5)
F2—C16	1.364 (4)	C21—C22	1.376 (5)
F4—C21	1.368 (4)	C21—C20	1.376 (5)
O1—C5	1.365 (4)	C1—H1	1
O1—C10	1.432 (4)	C22—H22	0.95
N1—C11	1.424 (5)	C13—H13	0.95
N1—C1	1.471 (5)	C13—C12	1.378 (5)
N1—C2	1.465 (4)	C13—C14	1.378 (6)
C5—C4	1.380 (5)	C7—H7	0.95
C5—C6	1.400 (5)	C7—C6	1.374 (5)
C11—C16	1.386 (5)	C20—H20	0.95
C11—C12	1.388 (5)	C2—H2A	0.99
C9—C8	1.387 (5)	C2—H2B	0.99
C9—C4	1.403 (5)	C2—C3	1.514 (5)
C9—C3	1.506 (5)	C6—H6	0.95
C8—C1	1.512 (5)	C3—H3A	0.99
C8—C7	1.396 (5)	C3—H3B	0.99
C4—H4	0.95	C15—H15	0.95
C17—C18	1.379 (5)	C15—C14	1.382 (6)
C17—C1	1.538 (5)	C10—H10A	0.98
C17—C22	1.387 (5)	C10—H10B	0.98
C16—C15	1.369 (5)	C10—H10C	0.98
C19—H19	0.95	C14—H14	0.95
C5—O1—C10	117.8 (3)	C21—C22—C17	119.4 (3)
C11—N1—C1	114.0 (3)	C21—C22—H22	120.3
C11—N1—C2	117.7 (3)	C12—C13—H13	121
C2—N1—C1	113.1 (3)	C12—C13—C14	118.1 (4)
O1—C5—C4	125.1 (3)	C14—C13—H13	121
O1—C5—C6	115.0 (3)	F1—C12—C11	117.8 (3)
C4—C5—C6	119.9 (3)	F1—C12—C13	118.2 (3)
C16—C11—N1	126.9 (3)	C13—C12—C11	123.9 (3)
C16—C11—C12	114.4 (3)	C8—C7—H7	119.2
C12—C11—N1	118.7 (3)	C6—C7—C8	121.6 (3)
C8—C9—C4	119.1 (3)	C6—C7—H7	119.2
C8—C9—C3	120.7 (3)	C19—C20—H20	121.4
C4—C9—C3	120.2 (3)	C21—C20—C19	117.2 (3)
C9—C8—C1	122.2 (3)	C21—C20—H20	121.4
C9—C8—C7	119.4 (3)	N1—C2—H2A	110.1
C7—C8—C1	118.4 (3)	N1—C2—H2B	110.1
C5—C4—C9	120.9 (3)	N1—C2—C3	108.2 (3)
C5—C4—H4	119.6	H2A—C2—H2B	108.4
C9—C4—H4	119.6	C3—C2—H2A	110.1
C18—C17—C1	121.5 (3)	C3—C2—H2B	110.1
C18—C17—C22	116.8 (3)	C5—C6—H6	120.5
C22—C17—C1	121.5 (3)	C7—C6—C5	119.1 (3)
F2—C16—C11	117.7 (3)	C7—C6—H6	120.5
F2—C16—C15	117.7 (3)	C9—C3—C2	112.9 (3)
C15—C16—C11	124.7 (4)	C9—C3—H3A	109
C18—C19—H19	120.3	C9—C3—H3B	109
C18—C19—C20	119.4 (3)	C2—C3—H3A	109
C20—C19—H19	120.3	C2—C3—H3B	109
F4—C21—C22	118.0 (3)	H3A—C3—H3B	107.8
F4—C21—C20	118.4 (3)	C16—C15—H15	121.1
C20—C21—C22	123.6 (4)	C16—C15—C14	117.8 (3)
F3—C18—C17	118.7 (3)	C14—C15—H15	121.1
F3—C18—C19	117.7 (3)	O1—C10—H10A	109.5
C19—C18—C17	123.6 (3)	O1—C10—H10B	109.5
N1—C1—C8	109.5 (3)	O1—C10—H10C	109.5
N1—C1—C17	112.0 (3)	H10A—C10—H10B	109.5
N1—C1—H1	107.7	H10A—C10—H10C	109.5
C8—C1—C17	111.9 (3)	H10B—C10—H10C	109.5
C8—C1—H1	107.7	C13—C14—C15	121.2 (4)
C17—C1—H1	107.7	C13—C14—H14	119.4
C17—C22—H22	120.3	C15—C14—H14	119.4
F2—C16—C15—C14	179.4 (3)	C1—N1—C11—C12	84.2 (4)
F4—C21—C22—C17	180.0 (3)	C1—N1—C2—C3	−67.9 (4)
F4—C21—C20—C19	178.2 (3)	C1—C8—C7—C6	179.5 (3)
O1—C5—C4—C9	178.5 (3)	C1—C17—C18—F3	−7.4 (5)
O1—C5—C6—C7	−179.0 (3)	C1—C17—C18—C19	173.2 (4)
N1—C11—C16—F2	−0.1 (6)	C1—C17—C22—C21	−173.2 (3)
N1—C11—C16—C15	179.8 (4)	C22—C17—C18—F3	177.1 (3)
N1—C11—C12—F1	1.4 (5)	C22—C17—C18—C19	−2.3 (5)
N1—C11—C12—C13	−179.7 (3)	C22—C17—C1—N1	86.5 (4)
N1—C2—C3—C9	46.1 (4)	C22—C17—C1—C8	−36.9 (5)
C11—N1—C1—C8	−169.4 (3)	C22—C21—C20—C19	−1.3 (6)
C11—N1—C1—C17	65.8 (4)	C12—C11—C16—F2	−179.4 (3)
C11—N1—C2—C3	155.6 (3)	C12—C11—C16—C15	0.4 (6)
C11—C16—C15—C14	−0.5 (6)	C12—C13—C14—C15	−0.1 (6)
C9—C8—C1—N1	−18.4 (4)	C7—C8—C1—N1	162.5 (3)
C9—C8—C1—C17	106.4 (4)	C7—C8—C1—C17	−72.7 (4)
C9—C8—C7—C6	0.4 (5)	C20—C19—C18—F3	−178.9 (3)
C8—C9—C4—C5	0.4 (5)	C20—C19—C18—C17	0.5 (6)
C8—C9—C3—C2	−15.3 (5)	C20—C21—C22—C17	−0.6 (6)
C8—C7—C6—C5	0.2 (6)	C2—N1—C11—C16	41.0 (5)
C4—C5—C6—C7	−0.6 (6)	C2—N1—C11—C12	−139.7 (3)
C4—C9—C8—C1	−179.8 (3)	C2—N1—C1—C8	52.5 (4)
C4—C9—C8—C7	−0.7 (5)	C2—N1—C1—C17	−72.3 (4)
C4—C9—C3—C2	165.7 (3)	C6—C5—C4—C9	0.2 (5)
C16—C11—C12—F1	−179.2 (3)	C3—C9—C8—C1	1.2 (5)
C16—C11—C12—C13	−0.3 (5)	C3—C9—C8—C7	−179.7 (3)
C16—C15—C14—C13	0.3 (6)	C3—C9—C4—C5	179.4 (3)
C18—C17—C1—N1	−88.8 (4)	C10—O1—C5—C4	6.0 (5)
C18—C17—C1—C8	147.8 (3)	C10—O1—C5—C6	−175.7 (3)
C18—C17—C22—C21	2.3 (5)	C14—C13—C12—F1	179.1 (3)
C18—C19—C20—C21	1.3 (5)	C14—C13—C12—C11	0.1 (6)
C1—N1—C11—C16	−95.1 (4)

(6-23)

Crystal data

C22H17F4NO	F(000) = 1600
Mr = 387.36	Dx = 1.438 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5244 reflections
a = 16.643 (3) Å	θ = 3.1–27.5°
b = 6.1042 (10) Å	µ = 0.12 mm^−1
c = 35.217 (7) Å	T = 100 K
V = 3577.8 (11) Å^3	Block, clear light colourless
Z = 8	0.3 × 0.1 × 0.1 mm

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2658 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.134
profile data from ω–scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan Blessing 1995	h = −19→21
Tmin = 0.809, Tmax = 1	k = −7→7
22278 measured reflections	l = −45→45
4056 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.090	H-atom parameters constrained
wR(F^2) = 0.257	w = 1/[σ^2(Fo^2) + (0.128P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
4056 reflections	Δρmax = 0.35 e Å^−3
258 parameters	Δρmin = −0.30 e Å^−3

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)
F1	0.70311 (11)	0.9182 (3)	0.41751 (5)	0.0347 (5)
F2	0.55386 (13)	0.2761 (3)	0.43739 (6)	0.0483 (6)
F3A	0.36031 (19)	0.9050 (6)	0.44782 (9)	0.0462 (8)	0.652 (4)
F3B	0.3126 (4)	0.3663 (10)	0.36523 (16)	0.0462 (8)	0.348 (4)
F4	0.26288 (13)	0.6155 (4)	0.41718 (7)	0.0585 (7)
O1	0.62593 (16)	0.6603 (4)	0.20393 (7)	0.0432 (7)
N1	0.63223 (16)	0.5661 (4)	0.38496 (7)	0.0300 (6)
C1	0.5801 (2)	0.7183 (5)	0.36328 (9)	0.0298 (7)
H1A	0.5974	0.8703	0.37	0.036*	0.652 (4)
H1B	0.5974	0.8703	0.37	0.036*	0.348 (4)
C2	0.6347 (2)	0.3442 (5)	0.36978 (10)	0.0352 (8)
H2A	0.5795	0.2864	0.3668	0.042*
H2B	0.6645	0.2469	0.3873	0.042*
C3	0.6764 (2)	0.3514 (5)	0.33171 (9)	0.0354 (8)
H3A	0.734	0.3855	0.3355	0.042*
H3B	0.6726	0.2059	0.3194	0.042*
C4	0.6517 (2)	0.5086 (5)	0.26689 (9)	0.0342 (8)
H4	0.6833	0.3932	0.2567	0.041*
C5	0.6183 (2)	0.6619 (5)	0.24299 (9)	0.0331 (8)
C6	0.5719 (2)	0.8313 (5)	0.25754 (9)	0.0350 (8)
H6	0.5485	0.9363	0.241	0.042*
C7	0.5602 (2)	0.8460 (5)	0.29616 (9)	0.0334 (8)
H7	0.529	0.9626	0.3062	0.04*
C8	0.59383 (19)	0.6907 (5)	0.32079 (9)	0.0309 (7)
C9	0.63924 (19)	0.5220 (5)	0.30614 (9)	0.0323 (7)
C10	0.6685 (3)	0.4798 (6)	0.18781 (11)	0.0490 (10)
H10A	0.6665	0.4896	0.1601	0.074*
H10B	0.6436	0.3423	0.196	0.074*
H10C	0.7246	0.4836	0.1963	0.074*
C11	0.63015 (19)	0.5928 (5)	0.42456 (9)	0.0297 (7)
C12	0.5954 (2)	0.4517 (6)	0.45075 (10)	0.0360 (8)
C13	0.6003 (2)	0.4768 (6)	0.48952 (10)	0.0394 (8)
H13	0.5772	0.3708	0.506	0.047*
C14	0.6390 (2)	0.6568 (6)	0.50415 (10)	0.0405 (9)
H14	0.6423	0.6772	0.5308	0.049*
C15	0.6734 (2)	0.8092 (6)	0.47961 (10)	0.0357 (8)
H15	0.6996	0.9359	0.4892	0.043*
C16	0.66849 (19)	0.7718 (5)	0.44123 (9)	0.0317 (7)
C17A	0.49246 (19)	0.6963 (5)	0.37528 (9)	0.0294 (7)	0.652 (4)
C17B	0.49246 (19)	0.6963 (5)	0.37528 (9)	0.0294 (7)	0.348 (4)
C18A	0.4646 (2)	0.8260 (6)	0.40485 (9)	0.0346 (8)	0.652 (4)
H18A	0.4984	0.935	0.4156	0.041*	0.652 (4)
C18B	0.4646 (2)	0.8260 (6)	0.40485 (9)	0.0346 (8)	0.348 (4)
H18B	0.4984	0.935	0.4156	0.041*	0.348 (4)
C19A	0.3877 (2)	0.7964 (6)	0.41862 (10)	0.0397 (8)	0.652 (4)
C19B	0.3877 (2)	0.7964 (6)	0.41862 (10)	0.0397 (8)	0.348 (4)
H19B	0.3688	0.8847	0.439	0.048*	0.348 (4)
C20A	0.3390 (2)	0.6431 (7)	0.40335 (11)	0.0431 (9)	0.652 (4)
C20B	0.3390 (2)	0.6431 (7)	0.40335 (11)	0.0431 (9)	0.348 (4)
C21A	0.3651 (2)	0.5132 (6)	0.37391 (11)	0.0409 (9)	0.652 (4)
H21A	0.3306	0.4052	0.3634	0.049*	0.652 (4)
C21B	0.3651 (2)	0.5132 (6)	0.37391 (11)	0.0409 (9)	0.348 (4)
C22A	0.4418 (2)	0.5407 (5)	0.35972 (10)	0.0337 (8)	0.652 (4)
H22A	0.4599	0.4524	0.3392	0.04*	0.652 (4)
C22B	0.4418 (2)	0.5407 (5)	0.35972 (10)	0.0337 (8)	0.348 (4)
H22B	0.4599	0.4524	0.3392	0.04*	0.348 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0379 (11)	0.0298 (10)	0.0363 (10)	−0.0059 (8)	0.0002 (8)	0.0020 (8)
F2	0.0570 (13)	0.0407 (12)	0.0472 (13)	−0.0192 (10)	−0.0013 (10)	0.0068 (10)
F3A	0.0434 (16)	0.0534 (17)	0.0417 (16)	0.0080 (14)	0.0029 (13)	−0.0051 (13)
F3B	0.0434 (16)	0.0534 (17)	0.0417 (16)	0.0080 (14)	0.0029 (13)	−0.0051 (13)
F4	0.0369 (12)	0.0615 (15)	0.0770 (17)	−0.0009 (11)	0.0131 (11)	0.0132 (13)
O1	0.0548 (16)	0.0428 (14)	0.0319 (13)	0.0048 (12)	0.0040 (11)	−0.0014 (11)
N1	0.0366 (15)	0.0268 (13)	0.0264 (14)	0.0022 (12)	−0.0025 (11)	0.0026 (11)
C1	0.0332 (17)	0.0235 (14)	0.0327 (16)	0.0008 (14)	−0.0035 (14)	0.0024 (13)
C2	0.0412 (19)	0.0264 (17)	0.0382 (19)	−0.0013 (15)	−0.0082 (15)	0.0005 (14)
C3	0.044 (2)	0.0253 (16)	0.0370 (19)	0.0021 (15)	−0.0033 (15)	−0.0016 (14)
C4	0.0355 (18)	0.0299 (16)	0.0373 (18)	−0.0026 (14)	0.0007 (14)	−0.0014 (14)
C5	0.0421 (19)	0.0305 (17)	0.0267 (16)	−0.0024 (15)	0.0037 (14)	−0.0015 (13)
C6	0.0395 (18)	0.0357 (18)	0.0298 (17)	0.0020 (15)	−0.0009 (14)	0.0054 (14)
C7	0.0339 (18)	0.0293 (16)	0.0371 (18)	0.0040 (14)	0.0029 (14)	−0.0001 (14)
C8	0.0315 (17)	0.0283 (15)	0.0329 (17)	0.0006 (14)	−0.0034 (14)	0.0007 (13)
C9	0.0300 (17)	0.0307 (17)	0.0364 (17)	−0.0037 (14)	−0.0008 (14)	−0.0008 (14)
C10	0.060 (3)	0.046 (2)	0.041 (2)	0.003 (2)	0.0037 (18)	−0.0062 (17)
C11	0.0297 (16)	0.0275 (16)	0.0318 (17)	0.0005 (14)	−0.0025 (13)	0.0039 (13)
C12	0.0341 (18)	0.0361 (17)	0.0379 (18)	−0.0052 (15)	−0.0009 (15)	−0.0003 (15)
C13	0.0403 (19)	0.0408 (19)	0.0371 (19)	0.0015 (16)	0.0045 (15)	0.0117 (16)
C14	0.042 (2)	0.046 (2)	0.0329 (18)	0.0081 (17)	0.0010 (16)	0.0019 (16)
C15	0.0392 (19)	0.0345 (18)	0.0335 (17)	0.0049 (15)	0.0002 (15)	−0.0030 (14)
C16	0.0312 (16)	0.0299 (16)	0.0340 (18)	0.0047 (14)	0.0030 (14)	0.0038 (14)
C17A	0.0321 (17)	0.0254 (14)	0.0306 (16)	−0.0015 (14)	−0.0025 (13)	0.0065 (12)
C17B	0.0321 (17)	0.0254 (14)	0.0306 (16)	−0.0015 (14)	−0.0025 (13)	0.0065 (12)
C18A	0.0361 (18)	0.0370 (17)	0.0306 (17)	−0.0014 (15)	−0.0011 (14)	0.0005 (14)
C18B	0.0361 (18)	0.0370 (17)	0.0306 (17)	−0.0014 (15)	−0.0011 (14)	0.0005 (14)
C19A	0.0378 (19)	0.048 (2)	0.0337 (18)	0.0055 (17)	0.0024 (15)	0.0034 (16)
C19B	0.0378 (19)	0.048 (2)	0.0337 (18)	0.0055 (17)	0.0024 (15)	0.0034 (16)
C20A	0.0281 (18)	0.049 (2)	0.052 (2)	0.0028 (17)	0.0025 (16)	0.0163 (18)
C20B	0.0281 (18)	0.049 (2)	0.052 (2)	0.0028 (17)	0.0025 (16)	0.0163 (18)
C21A	0.0345 (19)	0.0354 (19)	0.053 (2)	−0.0066 (16)	−0.0080 (16)	0.0053 (17)
C21B	0.0345 (19)	0.0354 (19)	0.053 (2)	−0.0066 (16)	−0.0080 (16)	0.0053 (17)
C22A	0.0335 (18)	0.0324 (17)	0.0351 (17)	0.0004 (14)	−0.0074 (14)	−0.0021 (14)
C22B	0.0335 (18)	0.0324 (17)	0.0351 (17)	0.0004 (14)	−0.0074 (14)	−0.0021 (14)

Geometric parameters (Å, º)

F1—C16	1.352 (4)	C10—H10A	0.98
F2—C12	1.360 (4)	C10—H10B	0.98
F3A—C19A	1.305 (5)	C10—H10C	0.98
F3B—C21B	1.289 (7)	C11—C12	1.388 (4)
F4—C20A	1.368 (4)	C11—C16	1.395 (5)
F4—C20B	1.368 (4)	C12—C13	1.376 (5)
O1—C5	1.381 (4)	C13—H13	0.95
O1—C10	1.427 (4)	C13—C14	1.374 (5)
N1—C1	1.483 (4)	C14—H14	0.95
N1—C2	1.457 (4)	C14—C15	1.393 (5)
N1—C11	1.405 (4)	C15—H15	0.95
C1—H1A	1	C15—C16	1.373 (4)
C1—H1B	1	C17A—C18A	1.388 (5)
C1—C8	1.523 (4)	C17A—C22A	1.383 (4)
C1—C17A	1.525 (4)	C17B—C18B	1.388 (5)
C1—C17B	1.525 (4)	C17B—C22B	1.383 (4)
C2—H2A	0.99	C18A—H18A	0.95
C2—H2B	0.99	C18A—C19A	1.381 (5)
C2—C3	1.510 (5)	C18B—H18B	0.95
C3—H3A	0.99	C18B—C19B	1.381 (5)
C3—H3B	0.99	C19A—C20A	1.350 (5)
C3—C9	1.509 (5)	C19B—H19B	0.95
C4—H4	0.95	C19B—C20B	1.350 (5)
C4—C5	1.376 (5)	C20A—C21A	1.376 (6)
C4—C9	1.400 (4)	C20B—C21B	1.376 (6)
C5—C6	1.388 (4)	C21A—H21A	0.95
C6—H6	0.95	C21A—C22A	1.381 (5)
C6—C7	1.377 (4)	C21B—C22B	1.381 (5)
C7—H7	0.95	C22A—H22A	0.95
C7—C8	1.401 (4)	C22B—H22B	0.95
C8—C9	1.378 (4)
C5—O1—C10	116.6 (3)	C16—C11—N1	119.8 (3)
C2—N1—C1	114.2 (2)	F2—C12—C11	118.1 (3)
C11—N1—C1	115.1 (2)	F2—C12—C13	117.5 (3)
C11—N1—C2	118.2 (3)	C13—C12—C11	124.4 (3)
N1—C1—H1A	106.9	C12—C13—H13	120.4
N1—C1—H1B	106.9	C14—C13—C12	119.3 (3)
N1—C1—C8	110.4 (3)	C14—C13—H13	120.4
N1—C1—C17A	111.2 (2)	C13—C14—H14	120.2
N1—C1—C17B	111.2 (2)	C13—C14—C15	119.6 (3)
C8—C1—H1A	106.9	C15—C14—H14	120.2
C8—C1—H1B	106.9	C14—C15—H15	120.8
C8—C1—C17A	114.0 (3)	C16—C15—C14	118.4 (3)
C8—C1—C17B	114.0 (3)	C16—C15—H15	120.8
C17A—C1—H1A	106.9	F1—C16—C11	116.9 (3)
C17B—C1—H1B	106.9	F1—C16—C15	118.2 (3)
N1—C2—H2A	110.1	C15—C16—C11	124.9 (3)
N1—C2—H2B	110.1	C18A—C17A—C1	118.6 (3)
N1—C2—C3	108.2 (3)	C22A—C17A—C1	122.2 (3)
H2A—C2—H2B	108.4	C22A—C17A—C18A	119.0 (3)
C3—C2—H2A	110.1	C18B—C17B—C1	118.6 (3)
C3—C2—H2B	110.1	C22B—C17B—C1	122.2 (3)
C2—C3—H3A	109.4	C22B—C17B—C18B	119.0 (3)
C2—C3—H3B	109.4	C17A—C18A—H18A	120
H3A—C3—H3B	108	C19A—C18A—C17A	119.9 (3)
C9—C3—C2	111.2 (3)	C19A—C18A—H18A	120
C9—C3—H3A	109.4	C17B—C18B—H18B	120
C9—C3—H3B	109.4	C19B—C18B—C17B	119.9 (3)
C5—C4—H4	119.9	C19B—C18B—H18B	120
C5—C4—C9	120.3 (3)	F3A—C19A—C18A	122.2 (4)
C9—C4—H4	119.9	F3A—C19A—C20A	117.2 (3)
O1—C5—C6	115.1 (3)	C20A—C19A—C18A	120.5 (3)
C4—C5—O1	124.5 (3)	C18B—C19B—H19B	119.8
C4—C5—C6	120.4 (3)	C20B—C19B—C18B	120.5 (3)
C5—C6—H6	120.3	C20B—C19B—H19B	119.8
C7—C6—C5	119.5 (3)	F4—C20A—C21A	119.4 (3)
C7—C6—H6	120.3	C19A—C20A—F4	120.0 (4)
C6—C7—H7	119.6	C19A—C20A—C21A	120.7 (3)
C6—C7—C8	120.7 (3)	F4—C20B—C21B	119.4 (3)
C8—C7—H7	119.6	C19B—C20B—F4	120.0 (4)
C7—C8—C1	118.3 (3)	C19B—C20B—C21B	120.7 (3)
C9—C8—C1	122.2 (3)	C20A—C21A—H21A	120.2
C9—C8—C7	119.5 (3)	C20A—C21A—C22A	119.7 (3)
C4—C9—C3	119.2 (3)	C22A—C21A—H21A	120.2
C8—C9—C3	121.1 (3)	F3B—C21B—C20B	111.4 (4)
C8—C9—C4	119.6 (3)	F3B—C21B—C22B	128.7 (4)
O1—C10—H10A	109.5	C20B—C21B—C22B	119.7 (3)
O1—C10—H10B	109.5	C17A—C22A—H22A	119.9
O1—C10—H10C	109.5	C21A—C22A—C17A	120.2 (3)
H10A—C10—H10B	109.5	C21A—C22A—H22A	119.9
H10A—C10—H10C	109.5	C17B—C22B—H22B	119.9
H10B—C10—H10C	109.5	C21B—C22B—C17B	120.2 (3)
C12—C11—N1	126.7 (3)	C21B—C22B—H22B	119.9
C12—C11—C16	113.4 (3)
F2—C12—C13—C14	−177.4 (3)	C7—C8—C9—C4	0.4 (5)
F3A—C19A—C20A—F4	3.6 (5)	C8—C1—C17A—C18A	−144.8 (3)
F3A—C19A—C20A—C21A	−176.3 (4)	C8—C1—C17A—C22A	40.2 (4)
F3B—C21B—C22B—C17B	−173.7 (5)	C8—C1—C17B—C18B	−144.8 (3)
F4—C20A—C21A—C22A	179.8 (3)	C8—C1—C17B—C22B	40.2 (4)
F4—C20B—C21B—F3B	−4.9 (5)	C9—C4—C5—O1	−178.8 (3)
F4—C20B—C21B—C22B	179.8 (3)	C9—C4—C5—C6	0.0 (5)
O1—C5—C6—C7	179.5 (3)	C10—O1—C5—C4	3.1 (5)
N1—C1—C8—C7	−169.2 (3)	C10—O1—C5—C6	−175.8 (3)
N1—C1—C8—C9	9.4 (4)	C11—N1—C1—C8	174.0 (3)
N1—C1—C17A—C18A	89.6 (3)	C11—N1—C1—C17A	−58.4 (3)
N1—C1—C17A—C22A	−85.4 (4)	C11—N1—C1—C17B	−58.4 (3)
N1—C1—C17B—C18B	89.6 (3)	C11—N1—C2—C3	−152.4 (3)
N1—C1—C17B—C22B	−85.4 (4)	C11—C12—C13—C14	2.8 (6)
N1—C2—C3—C9	−51.9 (4)	C12—C11—C16—F1	−179.3 (3)
N1—C11—C12—F2	−5.0 (5)	C12—C11—C16—C15	0.7 (5)
N1—C11—C12—C13	174.8 (3)	C12—C13—C14—C15	−0.8 (5)
N1—C11—C16—F1	3.1 (4)	C13—C14—C15—C16	−1.1 (5)
N1—C11—C16—C15	−177.0 (3)	C14—C15—C16—F1	−178.9 (3)
C1—N1—C2—C3	67.3 (3)	C14—C15—C16—C11	1.1 (5)
C1—N1—C11—C12	108.8 (4)	C16—C11—C12—F2	177.6 (3)
C1—N1—C11—C16	−73.9 (4)	C16—C11—C12—C13	−2.7 (5)
C1—C8—C9—C3	1.5 (5)	C17A—C1—C8—C7	64.8 (4)
C1—C8—C9—C4	−178.2 (3)	C17A—C1—C8—C9	−116.6 (3)
C1—C17A—C18A—C19A	−174.3 (3)	C17A—C18A—C19A—F3A	175.8 (3)
C1—C17A—C22A—C21A	174.0 (3)	C17A—C18A—C19A—C20A	−0.5 (5)
C1—C17B—C18B—C19B	−174.3 (3)	C17B—C1—C8—C7	64.8 (4)
C1—C17B—C22B—C21B	174.0 (3)	C17B—C1—C8—C9	−116.6 (3)
C2—N1—C1—C8	−44.4 (4)	C17B—C18B—C19B—C20B	−0.5 (5)
C2—N1—C1—C17A	83.2 (3)	C18A—C17A—C22A—C21A	−1.0 (5)
C2—N1—C1—C17B	83.2 (3)	C18A—C19A—C20A—F4	−179.9 (3)
C2—N1—C11—C12	−31.2 (5)	C18A—C19A—C20A—C21A	0.2 (6)
C2—N1—C11—C16	146.1 (3)	C18B—C17B—C22B—C21B	−1.0 (5)
C2—C3—C9—C4	−160.3 (3)	C18B—C19B—C20B—F4	−179.9 (3)
C2—C3—C9—C8	20.0 (4)	C18B—C19B—C20B—C21B	0.2 (6)
C4—C5—C6—C7	0.6 (5)	C19A—C20A—C21A—C22A	−0.3 (6)
C5—C4—C9—C3	179.9 (3)	C19B—C20B—C21B—F3B	175.0 (4)
C5—C4—C9—C8	−0.5 (5)	C19B—C20B—C21B—C22B	−0.3 (6)
C5—C6—C7—C8	−0.7 (5)	C20A—C21A—C22A—C17A	0.7 (5)
C6—C7—C8—C1	178.8 (3)	C20B—C21B—C22B—C17B	0.7 (5)
C6—C7—C8—C9	0.2 (5)	C22A—C17A—C18A—C19A	0.9 (5)
C7—C8—C9—C3	−179.9 (3)	C22B—C17B—C18B—C19B	0.9 (5)

(6-25)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.489 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4671 reflections
a = 12.287 (2) Å	θ = 3.3–27.5°
b = 11.3169 (16) Å	µ = 0.12 mm^−1
c = 22.191 (4) Å	T = 100 K
β = 145.954 (6)°	Plate, clear light colourless
V = 1727.5 (5) Å^3	0.2 × 0.2 × 0.05 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2653 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.029
profile data from ω–scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan Blessing 1995	h = −12→14
Tmin = 0.897, Tmax = 1	k = −13→13
9203 measured reflections	l = −26→26
3048 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 0.7613P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3048 reflections	Δρmax = 0.25 e Å^−3
254 parameters	Δρmin = −0.25 e Å^−3

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
C8	0.2249 (2)	0.72391 (14)	0.61872 (12)	0.0195 (3)
C4	0.3663 (2)	0.73774 (14)	0.58421 (13)	0.0212 (3)
H4	0.4502	0.7069	0.5925	0.025*
C15	0.0370 (2)	0.44127 (15)	0.73539 (13)	0.0243 (4)
H15	−0.0155	0.4753	0.7469	0.029*
C17	0.3643 (2)	0.71764 (14)	0.78773 (12)	0.0192 (3)
C1	0.2156 (2)	0.66377 (13)	0.67552 (12)	0.0194 (3)
H1	0.0832	0.6787	0.6318	0.023*
C19	0.4608 (2)	0.87807 (14)	0.89717 (14)	0.0236 (4)
C12	0.1838 (2)	0.34100 (14)	0.69749 (12)	0.0209 (3)
H12	0.2294	0.305	0.6824	0.025*
C7	0.1095 (2)	0.82226 (14)	0.55285 (12)	0.0218 (4)
H7	0.0184	0.8497	0.54	0.026*
C13	0.1269 (2)	0.27249 (14)	0.71947 (12)	0.0223 (4)
C5	0.2569 (2)	0.83850 (14)	0.52277 (12)	0.0215 (4)
C9	0.3520 (2)	0.68222 (14)	0.63355 (13)	0.0212 (4)
C6	0.1269 (2)	0.87998 (14)	0.50627 (13)	0.0229 (4)
H6	0.0502	0.948	0.463	0.028*
C22	0.5340 (2)	0.65984 (15)	0.88284 (13)	0.0246 (4)
H22	0.5608	0.5836	0.8792	0.029*
C3	0.4684 (3)	0.57472 (15)	0.70266 (14)	0.0257 (4)
H3A	0.579	0.5977	0.7794	0.031*
H3B	0.5216	0.5392	0.6898	0.031*
C16	0.0993 (2)	0.51245 (15)	0.71704 (13)	0.0224 (4)
H16	0.0914	0.5959	0.7177	0.027*
C20	0.6300 (3)	0.82142 (16)	0.99097 (14)	0.0272 (4)
H20	0.7197	0.8571	1.0591	0.033*
C2	0.3436 (3)	0.48446 (15)	0.67797 (15)	0.0263 (4)
H2A	0.2485	0.4506	0.6057	0.032*
H2B	0.4274	0.4193	0.731	0.032*
C21	0.6650 (2)	0.71069 (16)	0.98284 (14)	0.0278 (4)
H21	0.7799	0.6691	1.0463	0.033*
C10	0.3929 (3)	0.86034 (17)	0.48680 (14)	0.0292 (4)
H10A	0.3796	0.91	0.4447	0.044*
H10B	0.3609	0.7784	0.4619	0.044*
H10C	0.527	0.8644	0.5631	0.044*
C18	0.3309 (2)	0.82718 (14)	0.79790 (12)	0.0201 (3)
C14	0.0521 (2)	0.32080 (15)	0.73672 (12)	0.0239 (4)
C11	0.1738 (2)	0.46464 (14)	0.69752 (12)	0.0197 (3)
N1	0.2394 (2)	0.53582 (12)	0.68117 (11)	0.0219 (3)
O1	0.26392 (17)	0.90145 (10)	0.47324 (9)	0.0261 (3)
F3	0.16558 (13)	0.88711 (8)	0.70918 (7)	0.0252 (2)
F2	−0.00326 (14)	0.24851 (9)	0.75736 (8)	0.0311 (3)
F4	0.41832 (15)	0.98552 (9)	0.90062 (8)	0.0321 (3)
F1	0.15068 (14)	0.15437 (8)	0.72718 (8)	0.0303 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0231 (8)	0.0166 (8)	0.0212 (8)	−0.0016 (6)	0.0188 (7)	−0.0016 (6)
C4	0.0218 (8)	0.0214 (8)	0.0231 (8)	−0.0024 (6)	0.0191 (7)	−0.0023 (6)
C15	0.0216 (8)	0.0286 (9)	0.0228 (8)	−0.0014 (7)	0.0184 (8)	−0.0006 (7)
C17	0.0228 (8)	0.0187 (8)	0.0247 (8)	−0.0011 (6)	0.0213 (7)	0.0010 (6)
C1	0.0213 (8)	0.0168 (8)	0.0231 (8)	0.0008 (6)	0.0190 (7)	−0.0003 (6)
C19	0.0302 (9)	0.0202 (8)	0.0292 (9)	−0.0025 (7)	0.0263 (8)	−0.0026 (7)
C12	0.0209 (8)	0.0201 (8)	0.0198 (8)	−0.0011 (6)	0.0165 (7)	−0.0016 (6)
C7	0.0242 (8)	0.0201 (8)	0.0227 (8)	0.0004 (7)	0.0198 (8)	−0.0018 (6)
C13	0.0204 (8)	0.0163 (8)	0.0175 (7)	−0.0023 (6)	0.0133 (7)	0.0000 (6)
C5	0.0255 (8)	0.0207 (8)	0.0196 (8)	−0.0065 (7)	0.0189 (7)	−0.0040 (6)
C9	0.0224 (8)	0.0181 (8)	0.0223 (8)	−0.0018 (6)	0.0184 (7)	−0.0015 (6)
C6	0.0270 (8)	0.0190 (8)	0.0214 (8)	0.0001 (7)	0.0198 (8)	−0.0002 (6)
C22	0.0263 (8)	0.0238 (9)	0.0285 (9)	0.0025 (7)	0.0236 (8)	0.0023 (7)
C3	0.0304 (9)	0.0244 (9)	0.0334 (9)	0.0058 (7)	0.0285 (8)	0.0053 (7)
C16	0.0240 (8)	0.0203 (8)	0.0243 (8)	0.0006 (7)	0.0202 (8)	0.0005 (6)
C20	0.0269 (9)	0.0300 (9)	0.0239 (8)	−0.0052 (7)	0.0210 (8)	−0.0037 (7)
C2	0.0364 (10)	0.0197 (8)	0.0377 (9)	0.0064 (7)	0.0335 (9)	0.0050 (7)
C21	0.0228 (8)	0.0322 (10)	0.0242 (8)	0.0030 (7)	0.0186 (8)	0.0042 (7)
C10	0.0267 (9)	0.0392 (10)	0.0260 (9)	−0.0022 (8)	0.0227 (8)	0.0015 (8)
C18	0.0224 (8)	0.0193 (8)	0.0231 (8)	0.0027 (6)	0.0197 (7)	0.0043 (6)
C14	0.0198 (8)	0.0289 (9)	0.0182 (8)	−0.0040 (7)	0.0149 (7)	0.0013 (7)
C11	0.0181 (8)	0.0207 (8)	0.0181 (7)	−0.0001 (6)	0.0146 (7)	0.0004 (6)
N1	0.0303 (7)	0.0157 (7)	0.0322 (7)	0.0008 (6)	0.0283 (7)	0.0002 (6)
O1	0.0300 (6)	0.0274 (7)	0.0281 (6)	0.0001 (5)	0.0254 (6)	0.0037 (5)
F3	0.0287 (5)	0.0219 (5)	0.0236 (5)	0.0073 (4)	0.0214 (5)	0.0040 (4)
F2	0.0320 (5)	0.0323 (6)	0.0311 (5)	−0.0061 (4)	0.0266 (5)	0.0023 (4)
F4	0.0427 (6)	0.0226 (5)	0.0322 (5)	0.0018 (4)	0.0313 (5)	−0.0029 (4)
F1	0.0337 (6)	0.0184 (5)	0.0319 (5)	−0.0010 (4)	0.0258 (5)	0.0019 (4)

Geometric parameters (Å, º)

C8—C1	1.518 (2)	C5—C6	1.391 (2)
C8—C7	1.397 (2)	C5—O1	1.3710 (19)
C8—C9	1.385 (2)	C9—C3	1.498 (2)
C4—H4	0.95	C6—H6	0.95
C4—C5	1.389 (2)	C22—H22	0.95
C4—C9	1.394 (2)	C22—C21	1.388 (2)
C15—H15	0.95	C3—H3A	0.99
C15—C16	1.384 (2)	C3—H3B	0.99
C15—C14	1.373 (2)	C3—C2	1.517 (2)
C17—C1	1.540 (2)	C16—H16	0.95
C17—C22	1.392 (2)	C16—C11	1.406 (2)
C17—C18	1.382 (2)	C20—H20	0.95
C1—H1	1	C20—C21	1.385 (3)
C1—N1	1.462 (2)	C2—H2A	0.99
C19—C20	1.376 (2)	C2—H2B	0.99
C19—C18	1.380 (2)	C2—N1	1.461 (2)
C19—F4	1.3506 (19)	C21—H21	0.95
C12—H12	0.95	C10—H10A	0.98
C12—C13	1.376 (2)	C10—H10B	0.98
C12—C11	1.405 (2)	C10—H10C	0.98
C7—H7	0.95	C10—O1	1.424 (2)
C7—C6	1.381 (2)	C18—F3	1.3545 (18)
C13—C14	1.368 (2)	C14—F2	1.3632 (19)
C13—F1	1.3487 (19)	C11—N1	1.384 (2)
C7—C8—C1	121.16 (14)	C21—C22—H22	119.2
C9—C8—C1	119.72 (14)	C9—C3—H3A	109.5
C9—C8—C7	119.11 (15)	C9—C3—H3B	109.5
C5—C4—H4	120.3	C9—C3—C2	110.79 (14)
C5—C4—C9	119.46 (15)	H3A—C3—H3B	108.1
C9—C4—H4	120.3	C2—C3—H3A	109.5
C16—C15—H15	120.5	C2—C3—H3B	109.5
C14—C15—H15	120.5	C15—C16—H16	119.1
C14—C15—C16	119.10 (16)	C15—C16—C11	121.78 (16)
C22—C17—C1	123.06 (14)	C11—C16—H16	119.1
C18—C17—C1	120.28 (14)	C19—C20—H20	121.1
C18—C17—C22	116.64 (15)	C19—C20—C21	117.87 (16)
C8—C1—C17	111.13 (13)	C21—C20—H20	121.1
C8—C1—H1	107.4	C3—C2—H2A	109.2
C17—C1—H1	107.4	C3—C2—H2B	109.2
N1—C1—C8	111.60 (13)	H2A—C2—H2B	107.9
N1—C1—C17	111.62 (13)	N1—C2—C3	112.27 (14)
N1—C1—H1	107.4	N1—C2—H2A	109.2
C20—C19—C18	121.33 (16)	N1—C2—H2B	109.2
F4—C19—C20	120.26 (15)	C22—C21—H21	119.7
F4—C19—C18	118.42 (15)	C20—C21—C22	120.62 (16)
C13—C12—H12	120.3	C20—C21—H21	119.7
C13—C12—C11	119.41 (15)	H10A—C10—H10B	109.5
C11—C12—H12	120.3	H10A—C10—H10C	109.5
C8—C7—H7	119.7	H10B—C10—H10C	109.5
C6—C7—C8	120.56 (15)	O1—C10—H10A	109.5
C6—C7—H7	119.7	O1—C10—H10B	109.5
C14—C13—C12	122.03 (15)	O1—C10—H10C	109.5
F1—C13—C12	118.87 (15)	C19—C18—C17	121.84 (15)
F1—C13—C14	119.08 (15)	F3—C18—C17	120.16 (14)
C4—C5—C6	120.09 (15)	F3—C18—C19	117.99 (14)
O1—C5—C4	124.14 (15)	C13—C14—C15	120.06 (15)
O1—C5—C6	115.75 (14)	F2—C14—C15	120.46 (15)
C8—C9—C4	120.74 (15)	F2—C14—C13	119.46 (15)
C8—C9—C3	116.90 (14)	C12—C11—C16	117.56 (15)
C4—C9—C3	122.35 (15)	N1—C11—C12	120.66 (14)
C7—C6—C5	119.95 (15)	N1—C11—C16	121.76 (15)
C7—C6—H6	120	C2—N1—C1	120.74 (13)
C5—C6—H6	120	C11—N1—C1	118.72 (13)
C17—C22—H22	119.2	C11—N1—C2	120.37 (13)
C21—C22—C17	121.68 (16)	C5—O1—C10	117.31 (13)
C8—C1—N1—C2	25.3 (2)	C9—C8—C1—N1	−36.8 (2)
C8—C1—N1—C11	−159.33 (13)	C9—C8—C7—C6	−2.4 (2)
C8—C7—C6—C5	1.5 (2)	C9—C4—C5—C6	−3.2 (2)
C8—C9—C3—C2	41.9 (2)	C9—C4—C5—O1	178.25 (14)
C4—C5—C6—C7	1.3 (2)	C9—C3—C2—N1	−51.37 (19)
C4—C5—O1—C10	−0.4 (2)	C6—C5—O1—C10	−178.93 (14)
C4—C9—C3—C2	−136.96 (16)	C22—C17—C1—C8	−106.69 (17)
C15—C16—C11—C12	−0.2 (2)	C22—C17—C1—N1	18.6 (2)
C15—C16—C11—N1	−178.78 (14)	C22—C17—C18—C19	1.3 (2)
C17—C1—N1—C2	−99.69 (17)	C22—C17—C18—F3	−177.66 (14)
C17—C1—N1—C11	75.65 (18)	C3—C2—N1—C1	17.4 (2)
C17—C22—C21—C20	0.3 (3)	C3—C2—N1—C11	−157.85 (14)
C1—C8—C7—C6	176.51 (14)	C16—C15—C14—C13	−0.4 (2)
C1—C8—C9—C4	−178.50 (14)	C16—C15—C14—F2	178.28 (14)
C1—C8—C9—C3	2.6 (2)	C16—C11—N1—C1	−5.0 (2)
C1—C17—C22—C21	−179.84 (15)	C16—C11—N1—C2	170.34 (15)
C1—C17—C18—C19	179.92 (15)	C20—C19—C18—C17	−0.3 (3)
C1—C17—C18—F3	1.0 (2)	C20—C19—C18—F3	178.65 (14)
C19—C20—C21—C22	0.8 (3)	C18—C17—C1—C8	74.79 (18)
C12—C13—C14—C15	−1.8 (2)	C18—C17—C1—N1	−159.93 (14)
C12—C13—C14—F2	179.50 (13)	C18—C17—C22—C21	−1.3 (2)
C12—C11—N1—C1	176.42 (14)	C18—C19—C20—C21	−0.7 (3)
C12—C11—N1—C2	−8.2 (2)	C14—C15—C16—C11	1.3 (2)
C7—C8—C1—C17	−90.43 (18)	C11—C12—C13—C14	3.0 (2)
C7—C8—C1—N1	144.28 (15)	C11—C12—C13—F1	−175.09 (14)
C7—C8—C9—C4	0.4 (2)	O1—C5—C6—C7	179.94 (14)
C7—C8—C9—C3	−178.48 (14)	F4—C19—C20—C21	179.11 (15)
C13—C12—C11—C16	−2.0 (2)	F4—C19—C18—C17	179.84 (14)
C13—C12—C11—N1	176.66 (14)	F4—C19—C18—F3	−1.2 (2)
C5—C4—C9—C8	2.4 (2)	F1—C13—C14—C15	176.27 (14)
C5—C4—C9—C3	−178.78 (15)	F1—C13—C14—F2	−2.4 (2)
C9—C8—C1—C17	88.47 (17)

(6-30)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.484 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5100 reflections
a = 12.947 (3) Å	θ = 3.2–27.5°
b = 10.4113 (18) Å	µ = 0.12 mm^−1
c = 22.590 (5) Å	T = 100 K
β = 145.306 (10)°	Block, clear light colourless
V = 1733.2 (7) Å^3	0.34 × 0.3 × 0.25 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3584 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.027
profile data from ω–scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan Blessing 1995	h = −16→16
Tmin = 0.912, Tmax = 1	k = −13→13
18101 measured reflections	l = −29→29
3967 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 0.5445P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3967 reflections	Δρmax = 0.31 e Å^−3
254 parameters	Δρmin = −0.24 e Å^−3

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
C9	0.34149 (15)	0.64483 (11)	0.12989 (9)	0.0167 (2)
C4	0.34921 (16)	0.71295 (11)	0.08035 (9)	0.0180 (2)
H4	0.4121	0.6794	0.0778	0.022*
C5	0.26245 (16)	0.83109 (11)	0.03478 (9)	0.0181 (2)
C6	0.16506 (16)	0.87981 (11)	0.03687 (9)	0.0192 (2)
H6	0.107	0.9588	0.0064	0.023*
C7	0.15508 (15)	0.81048 (11)	0.08422 (9)	0.0173 (2)
H7	0.0887	0.8428	0.0847	0.021*
C8	0.24354 (15)	0.69228 (11)	0.13150 (8)	0.0154 (2)
C1	0.23821 (15)	0.62224 (11)	0.18806 (9)	0.0151 (2)
H1	0.1146	0.6296	0.1454	0.018*
C2	0.32832 (17)	0.42812 (11)	0.16877 (10)	0.0197 (2)
H2A	0.218	0.405	0.0959	0.024*
H2B	0.3975	0.3502	0.208	0.024*
C3	0.43843 (17)	0.51923 (12)	0.18273 (10)	0.0205 (2)
H3A	0.5557	0.5338	0.2563	0.025*
H3B	0.4587	0.481	0.1537	0.025*
C11	0.21179 (14)	0.40402 (11)	0.21437 (8)	0.0157 (2)
C12	0.20448 (15)	0.27032 (11)	0.20182 (9)	0.0175 (2)
H12	0.2395	0.2358	0.1821	0.021*
C13	0.14563 (16)	0.19062 (11)	0.21872 (9)	0.0189 (2)
C14	0.08905 (16)	0.23803 (12)	0.24581 (9)	0.0197 (2)
C15	0.08961 (16)	0.36873 (12)	0.25564 (9)	0.0202 (2)
H15	0.0491	0.4017	0.2725	0.024*
C16	0.15056 (16)	0.45120 (11)	0.24041 (9)	0.0188 (2)
H16	0.151	0.5393	0.2475	0.023*
C17	0.36552 (15)	0.69098 (11)	0.29149 (9)	0.0149 (2)
C18	0.55086 (16)	0.66322 (11)	0.37941 (9)	0.0182 (2)
H18	0.5988	0.6003	0.3773	0.022*
C19	0.66095 (15)	0.73131 (12)	0.46926 (9)	0.0201 (2)
C20	0.59920 (16)	0.82502 (11)	0.47833 (9)	0.0201 (2)
H20	0.6767	0.8696	0.54	0.024*
C21	0.41454 (16)	0.84833 (11)	0.38970 (9)	0.0186 (2)
C22	0.29666 (15)	0.78448 (11)	0.29681 (9)	0.0164 (2)
H22	0.1734	0.8037	0.2388	0.02*
C10	0.36521 (18)	0.86023 (14)	−0.01582 (10)	0.0257 (3)
H10A	0.3562	0.9207	−0.052	0.039*
H10B	0.318	0.7787	−0.0506	0.039*
H10C	0.4901	0.8506	0.0543	0.039*
N1	0.28099 (13)	0.48519 (9)	0.20352 (8)	0.0165 (2)
O1	0.26318 (12)	0.90573 (9)	−0.01450 (7)	0.0225 (2)
F1	0.14272 (10)	0.06292 (7)	0.20750 (6)	0.02572 (19)
F2	0.03188 (10)	0.15588 (7)	0.26155 (6)	0.02517 (18)
F3	0.84151 (10)	0.70554 (8)	0.55424 (6)	0.0300 (2)
F4	0.34640 (10)	0.93732 (7)	0.39504 (6)	0.02634 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C9	0.0164 (5)	0.0169 (5)	0.0169 (5)	−0.0007 (4)	0.0137 (5)	−0.0010 (4)
C4	0.0182 (5)	0.0203 (6)	0.0185 (5)	−0.0021 (4)	0.0157 (5)	−0.0025 (4)
C5	0.0186 (5)	0.0194 (5)	0.0152 (5)	−0.0035 (4)	0.0137 (5)	−0.0018 (4)
C6	0.0197 (5)	0.0172 (5)	0.0179 (5)	0.0012 (4)	0.0149 (5)	0.0017 (4)
C7	0.0170 (5)	0.0174 (5)	0.0173 (5)	0.0003 (4)	0.0140 (5)	−0.0006 (4)
C8	0.0149 (5)	0.0160 (5)	0.0144 (5)	−0.0019 (4)	0.0119 (5)	−0.0018 (4)
C1	0.0149 (5)	0.0138 (5)	0.0167 (5)	0.0005 (4)	0.0130 (5)	−0.0002 (4)
C2	0.0273 (6)	0.0154 (5)	0.0267 (6)	0.0024 (4)	0.0242 (5)	0.0003 (4)
C3	0.0244 (6)	0.0185 (6)	0.0272 (6)	0.0043 (5)	0.0230 (5)	0.0033 (5)
C11	0.0147 (5)	0.0149 (5)	0.0156 (5)	−0.0002 (4)	0.0121 (5)	−0.0001 (4)
C12	0.0175 (5)	0.0159 (5)	0.0171 (5)	0.0000 (4)	0.0138 (5)	−0.0007 (4)
C13	0.0175 (5)	0.0129 (5)	0.0173 (5)	−0.0005 (4)	0.0125 (5)	−0.0001 (4)
C14	0.0176 (5)	0.0199 (6)	0.0186 (5)	−0.0034 (4)	0.0142 (5)	0.0011 (4)
C15	0.0204 (5)	0.0208 (6)	0.0222 (6)	−0.0010 (4)	0.0181 (5)	−0.0008 (4)
C16	0.0205 (5)	0.0156 (5)	0.0225 (6)	−0.0014 (4)	0.0181 (5)	−0.0018 (4)
C17	0.0172 (5)	0.0139 (5)	0.0164 (5)	−0.0007 (4)	0.0144 (5)	0.0004 (4)
C18	0.0188 (5)	0.0178 (5)	0.0200 (6)	0.0022 (4)	0.0164 (5)	0.0017 (4)
C19	0.0143 (5)	0.0237 (6)	0.0167 (5)	0.0007 (4)	0.0116 (5)	0.0018 (4)
C20	0.0214 (6)	0.0201 (6)	0.0165 (5)	−0.0029 (4)	0.0152 (5)	−0.0024 (4)
C21	0.0232 (6)	0.0161 (5)	0.0215 (6)	0.0014 (4)	0.0194 (5)	−0.0003 (4)
C22	0.0167 (5)	0.0168 (5)	0.0169 (5)	0.0015 (4)	0.0141 (5)	0.0010 (4)
C10	0.0251 (6)	0.0351 (7)	0.0245 (6)	−0.0009 (5)	0.0219 (6)	0.0020 (5)
N1	0.0209 (5)	0.0127 (4)	0.0222 (5)	0.0004 (4)	0.0190 (4)	−0.0005 (4)
O1	0.0280 (4)	0.0226 (4)	0.0248 (4)	−0.0005 (4)	0.0233 (4)	0.0022 (3)
F1	0.0313 (4)	0.0128 (3)	0.0304 (4)	−0.0009 (3)	0.0248 (4)	0.0001 (3)
F2	0.0275 (4)	0.0232 (4)	0.0279 (4)	−0.0050 (3)	0.0234 (4)	0.0010 (3)
F3	0.0142 (3)	0.0384 (5)	0.0193 (4)	0.0018 (3)	0.0102 (3)	−0.0028 (3)
F4	0.0281 (4)	0.0263 (4)	0.0238 (4)	0.0044 (3)	0.0212 (4)	−0.0040 (3)

Geometric parameters (Å, º)

C9—C4	1.3961 (16)	C12—H12	0.93
C9—C8	1.3891 (16)	C12—C13	1.3760 (16)
C9—C3	1.4987 (16)	C13—C14	1.3755 (17)
C4—H4	0.93	C13—F1	1.3482 (13)
C4—C5	1.3903 (17)	C14—C15	1.3779 (17)
C5—C6	1.3955 (17)	C14—F2	1.3561 (13)
C5—O1	1.3639 (14)	C15—H15	0.93
C6—H6	0.93	C15—C16	1.3874 (16)
C6—C7	1.3818 (16)	C16—H16	0.93
C7—H7	0.93	C17—C18	1.3962 (16)
C7—C8	1.3984 (16)	C17—C22	1.3903 (15)
C8—C1	1.5211 (15)	C18—H18	0.93
C1—H1	0.98	C18—C19	1.3771 (17)
C1—C17	1.5348 (16)	C19—C20	1.3793 (17)
C1—N1	1.4650 (14)	C19—F3	1.3574 (14)
C2—H2A	0.97	C20—H20	0.93
C2—H2B	0.97	C20—C21	1.3828 (17)
C2—C3	1.5141 (17)	C21—C22	1.3814 (16)
C2—N1	1.4616 (14)	C21—F4	1.3514 (13)
C3—H3A	0.97	C22—H22	0.93
C3—H3B	0.97	C10—H10A	0.96
C11—C12	1.4082 (15)	C10—H10B	0.96
C11—C16	1.4081 (15)	C10—H10C	0.96
C11—N1	1.3921 (14)	C10—O1	1.4267 (15)
C4—C9—C3	121.11 (10)	C13—C12—H12	120
C8—C9—C4	120.59 (11)	C14—C13—C12	121.74 (11)
C8—C9—C3	118.30 (10)	F1—C13—C12	118.61 (11)
C9—C4—H4	120.1	F1—C13—C14	119.65 (11)
C5—C4—C9	119.75 (11)	C13—C14—C15	119.48 (11)
C5—C4—H4	120.1	F2—C14—C13	119.71 (11)
C4—C5—C6	119.93 (11)	F2—C14—C15	120.81 (11)
O1—C5—C4	124.39 (11)	C14—C15—H15	120
O1—C5—C6	115.67 (10)	C14—C15—C16	119.98 (11)
C5—C6—H6	120	C16—C15—H15	120
C7—C6—C5	119.90 (11)	C11—C16—H16	119.4
C7—C6—H6	120	C15—C16—C11	121.21 (11)
C6—C7—H7	119.6	C15—C16—H16	119.4
C6—C7—C8	120.78 (11)	C18—C17—C1	120.49 (10)
C8—C7—H7	119.6	C22—C17—C1	119.72 (10)
C9—C8—C7	119.02 (10)	C22—C17—C18	119.76 (11)
C9—C8—C1	121.63 (10)	C17—C18—H18	120.8
C7—C8—C1	119.28 (10)	C19—C18—C17	118.40 (11)
C8—C1—H1	107.6	C19—C18—H18	120.8
C8—C1—C17	108.76 (9)	C18—C19—C20	123.99 (11)
C17—C1—H1	107.6	F3—C19—C18	118.34 (11)
N1—C1—C8	113.44 (9)	F3—C19—C20	117.67 (11)
N1—C1—H1	107.6	C19—C20—H20	122.2
N1—C1—C17	111.65 (9)	C19—C20—C21	115.62 (11)
H2A—C2—H2B	107.9	C21—C20—H20	122.2
C3—C2—H2A	109.2	C22—C21—C20	123.40 (11)
C3—C2—H2B	109.2	F4—C21—C20	118.01 (11)
N1—C2—H2A	109.2	F4—C21—C22	118.59 (10)
N1—C2—H2B	109.2	C17—C22—H22	120.6
N1—C2—C3	111.85 (10)	C21—C22—C17	118.82 (10)
C9—C3—C2	110.62 (10)	C21—C22—H22	120.6
C9—C3—H3A	109.5	H10A—C10—H10B	109.5
C9—C3—H3B	109.5	H10A—C10—H10C	109.5
C2—C3—H3A	109.5	H10B—C10—H10C	109.5
C2—C3—H3B	109.5	O1—C10—H10A	109.5
H3A—C3—H3B	108.1	O1—C10—H10B	109.5
C16—C11—C12	117.47 (10)	O1—C10—H10C	109.5
N1—C11—C12	120.74 (10)	C2—N1—C1	120.74 (9)
N1—C11—C16	121.78 (10)	C11—N1—C1	117.48 (9)
C11—C12—H12	120	C11—N1—C2	117.54 (9)
C13—C12—C11	120.08 (11)	C5—O1—C10	117.11 (10)
C9—C4—C5—C6	−1.31 (17)	C12—C11—N1—C1	163.00 (10)
C9—C4—C5—O1	179.32 (11)	C12—C11—N1—C2	5.92 (16)
C9—C8—C1—C17	102.63 (12)	C12—C13—C14—C15	0.51 (18)
C9—C8—C1—N1	−22.26 (15)	C12—C13—C14—F2	179.90 (10)
C4—C9—C8—C7	−1.06 (17)	C13—C14—C15—C16	−1.36 (18)
C4—C9—C8—C1	−177.89 (10)	C14—C15—C16—C11	0.30 (18)
C4—C9—C3—C2	−143.60 (11)	C16—C11—C12—C13	−2.39 (16)
C4—C5—C6—C7	−0.02 (17)	C16—C11—N1—C1	−18.46 (15)
C4—C5—O1—C10	−2.11 (17)	C16—C11—N1—C2	−175.54 (10)
C5—C6—C7—C8	0.82 (18)	C17—C1—N1—C2	−121.64 (11)
C6—C5—O1—C10	178.50 (10)	C17—C1—N1—C11	82.05 (12)
C6—C7—C8—C9	−0.28 (17)	C17—C18—C19—C20	0.63 (18)
C6—C7—C8—C1	176.62 (10)	C17—C18—C19—F3	−179.05 (10)
C7—C8—C1—C17	−74.19 (13)	C18—C17—C22—C21	0.17 (17)
C7—C8—C1—N1	160.92 (10)	C18—C19—C20—C21	0.06 (18)
C8—C9—C4—C5	1.85 (17)	C19—C20—C21—C22	−0.68 (18)
C8—C9—C3—C2	36.51 (15)	C19—C20—C21—F4	178.60 (10)
C8—C1—C17—C18	−84.30 (12)	C20—C21—C22—C17	0.57 (18)
C8—C1—C17—C22	93.67 (12)	C22—C17—C18—C19	−0.74 (17)
C8—C1—N1—C2	1.68 (14)	N1—C1—C17—C18	41.64 (14)
C8—C1—N1—C11	−154.63 (10)	N1—C1—C17—C22	−140.40 (10)
C1—C17—C18—C19	177.23 (10)	N1—C2—C3—C9	−54.50 (13)
C1—C17—C22—C21	−177.81 (10)	N1—C11—C12—C13	176.21 (10)
C3—C9—C4—C5	−178.03 (11)	N1—C11—C16—C15	−177.02 (11)
C3—C9—C8—C7	178.83 (10)	O1—C5—C6—C7	179.41 (10)
C3—C9—C8—C1	2.00 (16)	F1—C13—C14—C15	−179.01 (11)
C3—C2—N1—C1	36.15 (14)	F1—C13—C14—F2	0.38 (16)
C3—C2—N1—C11	−167.56 (10)	F2—C14—C15—C16	179.25 (10)
C11—C12—C13—C14	1.41 (17)	F3—C19—C20—C21	179.75 (10)
C11—C12—C13—F1	−179.06 (10)	F4—C21—C22—C17	−178.70 (10)
C12—C11—C16—C15	1.56 (17)

(6-31)

Crystal data

C22H17F4NO	Z = 4
Mr = 387.36	F(000) = 800
Triclinic, P1	Dx = 1.446 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1370 (1) Å	Cell parameters from 4585 reflections
b = 11.8983 (2) Å	θ = 3.1–27.5°
c = 15.127 Å	µ = 0.12 mm^−1
α = 73.675 (12)°	T = 100 K
β = 71.730 (13)°	Needle, clear light colourless
γ = 72.936 (11)°	0.35 × 0.22 × 0.15 mm
V = 1779.8 (2) Å^3

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	6683 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.026
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −14→14
Tmin = 0.923, Tmax = 1	k = −15→15
18292 measured reflections	l = −19→19
8136 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0632P)^2 + 0.4499P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
8136 reflections	Δρmax = 0.29 e Å^−3
507 parameters	Δρmin = −0.23 e Å^−3

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
F1	0.46884 (7)	0.17466 (7)	0.42907 (6)	0.02709 (19)
F3	−0.28616 (8)	0.27427 (7)	0.41457 (6)	0.02729 (19)
F7	0.19304 (8)	0.80497 (8)	0.10251 (7)	0.0306 (2)
F2	0.13307 (8)	−0.03111 (7)	0.52517 (6)	0.0282 (2)
F4	−0.29308 (9)	0.17869 (8)	0.27652 (7)	0.0367 (2)
F8	0.01415 (9)	0.94100 (8)	0.21589 (8)	0.0414 (2)
F6	0.99696 (9)	0.72274 (10)	0.06591 (7)	0.0423 (3)
F5	0.64283 (10)	1.04325 (9)	0.01535 (7)	0.0416 (2)
O2	0.31382 (10)	0.26210 (9)	0.11196 (7)	0.0271 (2)
O1	−0.43766 (10)	0.84618 (9)	0.36627 (8)	0.0276 (2)
N1	0.04437 (10)	0.39220 (10)	0.39888 (8)	0.0197 (2)
N2	0.57389 (11)	0.64721 (10)	0.15105 (8)	0.0220 (2)
C18	−0.18899 (13)	0.27892 (12)	0.33353 (10)	0.0217 (3)
C13	0.34214 (13)	0.17371 (12)	0.44325 (9)	0.0213 (3)
C11	0.12860 (12)	0.28560 (11)	0.42717 (9)	0.0186 (3)
C30	0.40677 (13)	0.56911 (12)	0.12729 (9)	0.0207 (3)
C12	0.25928 (13)	0.28250 (12)	0.41978 (9)	0.0198 (3)
H12	0.289	0.3532	0.3993	0.024*
C23	0.44605 (13)	0.68061 (12)	0.12990 (10)	0.0207 (3)
H23	0.4552	0.7315	0.0659	0.025*
C17	−0.08853 (12)	0.33155 (11)	0.32399 (10)	0.0198 (3)
C16	0.08838 (13)	0.17602 (12)	0.46298 (9)	0.0202 (3)
H16	0.0033	0.1737	0.4692	0.024*
C14	0.30664 (13)	0.06466 (12)	0.47878 (10)	0.0231 (3)
H14	0.3646	−0.0073	0.4947	0.028*
C29	0.34356 (13)	0.57029 (13)	0.06050 (10)	0.0229 (3)
H29	0.3227	0.6409	0.0169	0.027*
C26	0.41170 (13)	0.35680 (12)	0.18762 (10)	0.0227 (3)
H26	0.4366	0.2851	0.2289	0.027*
C5	−0.34723 (13)	0.73947 (12)	0.37396 (10)	0.0219 (3)
C39	0.34210 (13)	0.75568 (12)	0.19863 (10)	0.0221 (3)
C22	0.00916 (14)	0.33086 (13)	0.23946 (10)	0.0259 (3)
H22	0.0792	0.3636	0.2311	0.031*
C15	0.17699 (13)	0.07223 (12)	0.48861 (10)	0.0221 (3)
C8	−0.17867 (12)	0.51318 (12)	0.39762 (9)	0.0191 (3)
C7	−0.31007 (13)	0.52846 (12)	0.44581 (10)	0.0208 (3)
H7	−0.3414	0.4627	0.4862	0.025*
C31	0.43907 (13)	0.46212 (12)	0.19164 (9)	0.0215 (3)
C40	0.22214 (14)	0.81533 (12)	0.17965 (10)	0.0246 (3)
C1	−0.08782 (12)	0.38903 (11)	0.40326 (9)	0.0191 (3)
H1	−0.1213	0.3386	0.4646	0.023*
C28	0.31173 (13)	0.46695 (13)	0.05863 (10)	0.0234 (3)
H28	0.2669	0.4691	0.0154	0.028*
C27	0.34705 (13)	0.35961 (12)	0.12165 (10)	0.0230 (3)
C33	0.65565 (13)	0.72608 (13)	0.11377 (9)	0.0232 (3)
C9	−0.13198 (13)	0.61279 (12)	0.34006 (9)	0.0207 (3)
C25	0.50974 (14)	0.46581 (13)	0.26033 (10)	0.0242 (3)
H25A	0.5437	0.3847	0.2917	0.029*
H25B	0.4505	0.5089	0.3086	0.029*
C6	−0.39428 (13)	0.64033 (13)	0.43409 (10)	0.0234 (3)
H6	−0.4816	0.6494	0.4661	0.028*
C4	−0.21592 (13)	0.72644 (12)	0.32834 (10)	0.0221 (3)
H4	−0.184	0.7929	0.2902	0.026*
C19	−0.19259 (14)	0.22925 (12)	0.26211 (11)	0.0258 (3)
C24	0.62017 (14)	0.52843 (13)	0.20640 (10)	0.0248 (3)
H24A	0.6614	0.5369	0.2512	0.03*
H24B	0.6845	0.4796	0.1639	0.03*
C44	0.36475 (14)	0.77320 (13)	0.27875 (10)	0.0267 (3)
H44	0.4441	0.7354	0.2933	0.032*
C34	0.78936 (14)	0.68471 (14)	0.10924 (10)	0.0265 (3)
H34	0.8241	0.604	0.1312	0.032*
C3	0.01079 (13)	0.59413 (13)	0.29244 (11)	0.0258 (3)
H3A	0.0364	0.6702	0.2747	0.031*
H3B	0.0282	0.5651	0.2348	0.031*
C38	0.60756 (14)	0.84923 (13)	0.08051 (10)	0.0261 (3)
H38	0.5199	0.8795	0.0827	0.031*
C20	−0.09745 (15)	0.23120 (13)	0.17808 (11)	0.0292 (3)
H20	−0.1014	0.1991	0.1299	0.035*
C2	0.09023 (13)	0.50396 (12)	0.35821 (11)	0.0246 (3)
H2A	0.1803	0.4854	0.3228	0.03*
H2B	0.0861	0.54	0.4095	0.03*
C41	0.12922 (14)	0.88704 (13)	0.23847 (12)	0.0296 (3)
C42	0.15244 (15)	0.90402 (14)	0.31756 (11)	0.0328 (3)
H42	0.0901	0.953	0.3563	0.039*
C21	0.00438 (15)	0.28235 (14)	0.16728 (11)	0.0304 (3)
H21	0.0702	0.2843	0.1113	0.037*
C43	0.27190 (16)	0.84566 (14)	0.33774 (11)	0.0331 (3)
H43	0.2898	0.8551	0.3909	0.04*
C10	−0.39253 (16)	0.94863 (13)	0.30472 (11)	0.0310 (3)
H10A	−0.357	0.9347	0.2411	0.046*
H10B	−0.3266	0.9623	0.3263	0.046*
H10C	−0.4636	1.0178	0.3053	0.046*
C35	0.86761 (14)	0.76650 (16)	0.07156 (11)	0.0312 (3)
C37	0.69316 (16)	0.92398 (14)	0.04468 (11)	0.0302 (3)
C36	0.82489 (16)	0.88721 (16)	0.03805 (11)	0.0340 (4)
H36	0.8802	0.94	0.0129	0.041*
C32	0.34448 (17)	0.15063 (13)	0.17612 (11)	0.0330 (3)
H32A	0.3133	0.0909	0.1637	0.049*
H32B	0.3039	0.1606	0.2404	0.049*
H32C	0.4368	0.1254	0.1674	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0167 (4)	0.0307 (4)	0.0329 (5)	−0.0034 (3)	−0.0067 (3)	−0.0067 (3)
F3	0.0214 (4)	0.0256 (4)	0.0328 (5)	−0.0094 (3)	0.0017 (3)	−0.0082 (3)
F7	0.0275 (4)	0.0291 (5)	0.0401 (5)	−0.0059 (3)	−0.0159 (4)	−0.0071 (4)
F2	0.0274 (4)	0.0167 (4)	0.0370 (5)	−0.0060 (3)	−0.0071 (4)	−0.0001 (3)
F4	0.0290 (5)	0.0367 (5)	0.0528 (6)	−0.0161 (4)	−0.0038 (4)	−0.0203 (4)
F8	0.0233 (5)	0.0320 (5)	0.0653 (7)	0.0003 (4)	−0.0101 (4)	−0.0128 (5)
F6	0.0234 (5)	0.0651 (7)	0.0396 (5)	−0.0196 (4)	−0.0086 (4)	−0.0020 (5)
F5	0.0467 (6)	0.0312 (5)	0.0460 (6)	−0.0192 (4)	−0.0085 (5)	0.0004 (4)
O2	0.0328 (6)	0.0249 (5)	0.0271 (5)	−0.0100 (4)	−0.0075 (4)	−0.0071 (4)
O1	0.0257 (5)	0.0201 (5)	0.0348 (6)	0.0026 (4)	−0.0100 (4)	−0.0077 (4)
N1	0.0170 (5)	0.0167 (5)	0.0247 (6)	−0.0043 (4)	−0.0061 (4)	−0.0017 (4)
N2	0.0190 (5)	0.0240 (6)	0.0239 (6)	−0.0060 (4)	−0.0060 (5)	−0.0044 (5)
C18	0.0186 (6)	0.0163 (6)	0.0271 (7)	−0.0024 (5)	−0.0040 (5)	−0.0033 (5)
C13	0.0163 (6)	0.0277 (7)	0.0201 (6)	−0.0036 (5)	−0.0044 (5)	−0.0072 (5)
C11	0.0196 (6)	0.0197 (6)	0.0156 (6)	−0.0031 (5)	−0.0042 (5)	−0.0038 (5)
C30	0.0175 (6)	0.0238 (7)	0.0201 (6)	−0.0063 (5)	−0.0010 (5)	−0.0058 (5)
C12	0.0199 (6)	0.0211 (6)	0.0185 (6)	−0.0055 (5)	−0.0042 (5)	−0.0040 (5)
C23	0.0191 (6)	0.0228 (7)	0.0209 (6)	−0.0063 (5)	−0.0056 (5)	−0.0032 (5)
C17	0.0176 (6)	0.0165 (6)	0.0243 (7)	−0.0018 (5)	−0.0070 (5)	−0.0030 (5)
C16	0.0174 (6)	0.0200 (6)	0.0224 (6)	−0.0037 (5)	−0.0049 (5)	−0.0039 (5)
C14	0.0219 (7)	0.0211 (6)	0.0239 (7)	0.0006 (5)	−0.0072 (5)	−0.0048 (5)
C29	0.0213 (6)	0.0244 (7)	0.0212 (6)	−0.0038 (5)	−0.0049 (5)	−0.0039 (5)
C26	0.0217 (6)	0.0235 (7)	0.0211 (6)	−0.0052 (5)	−0.0027 (5)	−0.0050 (5)
C5	0.0237 (7)	0.0181 (6)	0.0255 (7)	0.0005 (5)	−0.0108 (5)	−0.0074 (5)
C39	0.0220 (7)	0.0196 (6)	0.0232 (7)	−0.0079 (5)	−0.0032 (5)	−0.0017 (5)
C22	0.0236 (7)	0.0290 (7)	0.0267 (7)	−0.0092 (6)	−0.0042 (6)	−0.0070 (6)
C15	0.0252 (7)	0.0173 (6)	0.0221 (6)	−0.0057 (5)	−0.0043 (5)	−0.0023 (5)
C8	0.0195 (6)	0.0199 (6)	0.0185 (6)	−0.0032 (5)	−0.0060 (5)	−0.0048 (5)
C7	0.0206 (6)	0.0208 (6)	0.0223 (6)	−0.0057 (5)	−0.0046 (5)	−0.0064 (5)
C31	0.0184 (6)	0.0258 (7)	0.0192 (6)	−0.0053 (5)	−0.0025 (5)	−0.0053 (5)
C40	0.0233 (7)	0.0223 (7)	0.0289 (7)	−0.0100 (5)	−0.0056 (6)	−0.0022 (5)
C1	0.0167 (6)	0.0185 (6)	0.0208 (6)	−0.0043 (5)	−0.0037 (5)	−0.0025 (5)
C28	0.0209 (6)	0.0305 (7)	0.0205 (6)	−0.0067 (5)	−0.0046 (5)	−0.0078 (5)
C27	0.0208 (6)	0.0259 (7)	0.0219 (6)	−0.0075 (5)	0.0005 (5)	−0.0086 (5)
C33	0.0235 (7)	0.0301 (7)	0.0182 (6)	−0.0097 (6)	−0.0020 (5)	−0.0082 (5)
C9	0.0214 (6)	0.0198 (6)	0.0201 (6)	−0.0036 (5)	−0.0058 (5)	−0.0033 (5)
C25	0.0242 (7)	0.0266 (7)	0.0213 (7)	−0.0073 (5)	−0.0065 (5)	−0.0018 (5)
C6	0.0166 (6)	0.0256 (7)	0.0293 (7)	−0.0035 (5)	−0.0048 (5)	−0.0104 (6)
C4	0.0251 (7)	0.0190 (6)	0.0217 (6)	−0.0043 (5)	−0.0075 (5)	−0.0023 (5)
C19	0.0221 (7)	0.0203 (7)	0.0379 (8)	−0.0062 (5)	−0.0083 (6)	−0.0081 (6)
C24	0.0234 (7)	0.0276 (7)	0.0236 (7)	−0.0061 (5)	−0.0086 (5)	−0.0024 (5)
C44	0.0267 (7)	0.0276 (7)	0.0246 (7)	−0.0057 (6)	−0.0047 (6)	−0.0058 (6)
C34	0.0241 (7)	0.0363 (8)	0.0210 (7)	−0.0099 (6)	−0.0049 (5)	−0.0065 (6)
C3	0.0220 (7)	0.0203 (7)	0.0277 (7)	−0.0045 (5)	−0.0018 (6)	0.0008 (5)
C38	0.0256 (7)	0.0313 (8)	0.0239 (7)	−0.0118 (6)	−0.0036 (6)	−0.0069 (6)
C20	0.0314 (8)	0.0273 (7)	0.0323 (8)	−0.0055 (6)	−0.0091 (6)	−0.0113 (6)
C2	0.0185 (6)	0.0197 (7)	0.0322 (7)	−0.0060 (5)	−0.0044 (5)	−0.0008 (5)
C41	0.0200 (7)	0.0221 (7)	0.0421 (9)	−0.0059 (5)	−0.0035 (6)	−0.0031 (6)
C42	0.0291 (8)	0.0262 (7)	0.0348 (8)	−0.0064 (6)	0.0056 (6)	−0.0088 (6)
C21	0.0284 (7)	0.0368 (8)	0.0262 (7)	−0.0104 (6)	−0.0006 (6)	−0.0104 (6)
C43	0.0376 (9)	0.0327 (8)	0.0265 (8)	−0.0087 (7)	−0.0019 (6)	−0.0084 (6)
C10	0.0373 (8)	0.0208 (7)	0.0299 (8)	0.0021 (6)	−0.0103 (7)	−0.0046 (6)
C35	0.0240 (7)	0.0528 (10)	0.0222 (7)	−0.0174 (7)	−0.0049 (6)	−0.0079 (6)
C37	0.0365 (8)	0.0311 (8)	0.0243 (7)	−0.0161 (6)	−0.0050 (6)	−0.0022 (6)
C36	0.0353 (8)	0.0480 (10)	0.0251 (7)	−0.0258 (7)	−0.0036 (6)	−0.0048 (7)
C32	0.0448 (9)	0.0236 (7)	0.0333 (8)	−0.0108 (6)	−0.0107 (7)	−0.0060 (6)

Geometric parameters (Å, º)

F1—C13	1.3621 (15)	C8—C1	1.5229 (18)
F3—C18	1.3573 (16)	C8—C9	1.3895 (18)
F7—C40	1.3502 (17)	C7—H7	0.93
F2—C15	1.3631 (15)	C7—C6	1.3862 (19)
F4—C19	1.3529 (16)	C31—C25	1.5032 (19)
F8—C41	1.3563 (18)	C40—C41	1.386 (2)
F6—C35	1.3643 (18)	C1—H1	0.98
F5—C37	1.3639 (18)	C28—H28	0.93
O2—C27	1.3733 (17)	C28—C27	1.397 (2)
O2—C32	1.4269 (18)	C33—C34	1.410 (2)
O1—C5	1.3711 (16)	C33—C38	1.407 (2)
O1—C10	1.4260 (18)	C9—C4	1.4005 (18)
N1—C11	1.3857 (16)	C9—C3	1.5037 (19)
N1—C1	1.4639 (16)	C25—H25A	0.97
N1—C2	1.4661 (17)	C25—H25B	0.97
N2—C23	1.4729 (17)	C25—C24	1.5167 (19)
N2—C33	1.3820 (18)	C6—H6	0.93
N2—C24	1.4636 (17)	C4—H4	0.93
C18—C17	1.3870 (19)	C19—C20	1.376 (2)
C18—C19	1.385 (2)	C24—H24A	0.97
C13—C12	1.3780 (19)	C24—H24B	0.97
C13—C14	1.3801 (19)	C44—H44	0.93
C11—C12	1.4145 (18)	C44—C43	1.393 (2)
C11—C16	1.4098 (18)	C34—H34	0.93
C30—C23	1.5276 (18)	C34—C35	1.381 (2)
C30—C29	1.3960 (19)	C3—H3A	0.97
C30—C31	1.3971 (19)	C3—H3B	0.97
C12—H12	0.93	C3—C2	1.5227 (19)
C23—H23	0.98	C38—H38	0.93
C23—C39	1.5426 (19)	C38—C37	1.377 (2)
C17—C22	1.3955 (19)	C20—H20	0.93
C17—C1	1.5415 (18)	C20—C21	1.384 (2)
C16—H16	0.93	C2—H2A	0.97
C16—C15	1.3801 (18)	C2—H2B	0.97
C14—H14	0.93	C41—C42	1.378 (2)
C14—C15	1.3826 (19)	C42—H42	0.93
C29—H29	0.93	C42—C43	1.392 (2)
C29—C28	1.386 (2)	C21—H21	0.93
C26—H26	0.93	C43—H43	0.93
C26—C31	1.3948 (19)	C10—H10A	0.96
C26—C27	1.390 (2)	C10—H10B	0.96
C5—C6	1.398 (2)	C10—H10C	0.96
C5—C4	1.390 (2)	C35—C36	1.374 (2)
C39—C40	1.393 (2)	C37—C36	1.382 (2)
C39—C44	1.393 (2)	C36—H36	0.93
C22—H22	0.93	C32—H32A	0.96
C22—C21	1.392 (2)	C32—H32B	0.96
C8—C7	1.3985 (18)	C32—H32C	0.96
C27—O2—C32	117.60 (11)	C38—C33—C34	118.55 (13)
C5—O1—C10	116.76 (11)	C8—C9—C4	120.53 (12)
C11—N1—C1	118.68 (11)	C8—C9—C3	117.75 (12)
C11—N1—C2	120.39 (11)	C4—C9—C3	121.72 (12)
C1—N1—C2	120.74 (11)	C31—C25—H25A	109.8
C33—N2—C23	119.94 (11)	C31—C25—H25B	109.8
C33—N2—C24	118.72 (11)	C31—C25—C24	109.15 (11)
C24—N2—C23	121.23 (11)	H25A—C25—H25B	108.3
F3—C18—C17	120.04 (12)	C24—C25—H25A	109.8
F3—C18—C19	118.45 (12)	C24—C25—H25B	109.8
C19—C18—C17	121.50 (13)	C5—C6—H6	120.2
F1—C13—C12	117.02 (12)	C7—C6—C5	119.66 (12)
F1—C13—C14	117.99 (12)	C7—C6—H6	120.2
C12—C13—C14	124.99 (12)	C5—C4—C9	119.71 (12)
N1—C11—C12	121.03 (12)	C5—C4—H4	120.1
N1—C11—C16	121.55 (12)	C9—C4—H4	120.1
C16—C11—C12	117.41 (12)	F4—C19—C18	118.32 (13)
C29—C30—C23	121.85 (12)	F4—C19—C20	120.22 (13)
C29—C30—C31	119.27 (12)	C20—C19—C18	121.46 (13)
C31—C30—C23	118.84 (12)	N2—C24—C25	111.37 (11)
C13—C12—C11	119.34 (12)	N2—C24—H24A	109.4
C13—C12—H12	120.3	N2—C24—H24B	109.4
C11—C12—H12	120.3	C25—C24—H24A	109.4
N2—C23—C30	110.50 (11)	C25—C24—H24B	109.4
N2—C23—H23	107.1	H24A—C24—H24B	108
N2—C23—C39	111.98 (11)	C39—C44—H44	119.1
C30—C23—H23	107.1	C43—C44—C39	121.88 (14)
C30—C23—C39	112.70 (11)	C43—C44—H44	119.1
C39—C23—H23	107.1	C33—C34—H34	120.7
C18—C17—C22	116.76 (13)	C35—C34—C33	118.61 (14)
C18—C17—C1	120.77 (12)	C35—C34—H34	120.7
C22—C17—C1	122.47 (12)	C9—C3—H3A	109.4
C11—C16—H16	120.5	C9—C3—H3B	109.4
C15—C16—C11	119.08 (12)	C9—C3—C2	111.02 (11)
C15—C16—H16	120.5	H3A—C3—H3B	108
C13—C14—H14	123.1	C2—C3—H3A	109.4
C13—C14—C15	113.83 (12)	C2—C3—H3B	109.4
C15—C14—H14	123.1	C33—C38—H38	120.7
C30—C29—H29	119.8	C37—C38—C33	118.57 (14)
C28—C29—C30	120.47 (13)	C37—C38—H38	120.7
C28—C29—H29	119.8	C19—C20—H20	121
C31—C26—H26	120.2	C19—C20—C21	118.06 (14)
C27—C26—H26	120.2	C21—C20—H20	121
C27—C26—C31	119.67 (13)	N1—C2—C3	112.56 (11)
O1—C5—C6	115.57 (12)	N1—C2—H2A	109.1
O1—C5—C4	124.34 (12)	N1—C2—H2B	109.1
C4—C5—C6	120.08 (12)	C3—C2—H2A	109.1
C40—C39—C23	120.63 (12)	C3—C2—H2B	109.1
C40—C39—C44	116.69 (13)	H2A—C2—H2B	107.8
C44—C39—C23	122.58 (12)	F8—C41—C40	118.12 (14)
C17—C22—H22	119.2	F8—C41—C42	120.52 (14)
C21—C22—C17	121.60 (13)	C42—C41—C40	121.35 (14)
C21—C22—H22	119.2	C41—C42—H42	121
F2—C15—C16	117.10 (12)	C41—C42—C43	118.06 (14)
F2—C15—C14	117.68 (12)	C43—C42—H42	121
C16—C15—C14	125.22 (13)	C22—C21—H21	119.7
C7—C8—C1	121.25 (12)	C20—C21—C22	120.60 (14)
C9—C8—C7	119.09 (12)	C20—C21—H21	119.7
C9—C8—C1	119.59 (11)	C44—C43—H43	119.8
C8—C7—H7	119.6	C42—C43—C44	120.42 (15)
C6—C7—C8	120.86 (12)	C42—C43—H43	119.8
C6—C7—H7	119.6	O1—C10—H10A	109.5
C30—C31—C25	116.80 (12)	O1—C10—H10B	109.5
C26—C31—C30	120.43 (13)	O1—C10—H10C	109.5
C26—C31—C25	122.69 (12)	H10A—C10—H10B	109.5
F7—C40—C39	120.57 (13)	H10A—C10—H10C	109.5
F7—C40—C41	117.84 (13)	H10B—C10—H10C	109.5
C41—C40—C39	121.59 (14)	F6—C35—C34	116.99 (15)
N1—C1—C17	110.95 (10)	F6—C35—C36	118.23 (14)
N1—C1—C8	112.36 (10)	C36—C35—C34	124.76 (15)
N1—C1—H1	107.8	F5—C37—C38	117.06 (14)
C17—C1—H1	107.8	F5—C37—C36	118.10 (13)
C8—C1—C17	109.96 (10)	C38—C37—C36	124.83 (15)
C8—C1—H1	107.8	C35—C36—C37	114.67 (14)
C29—C28—H28	120	C35—C36—H36	122.7
C29—C28—C27	119.96 (13)	C37—C36—H36	122.7
C27—C28—H28	120	O2—C32—H32A	109.5
O2—C27—C26	124.75 (13)	O2—C32—H32B	109.5
O2—C27—C28	115.13 (12)	O2—C32—H32C	109.5
C26—C27—C28	120.12 (13)	H32A—C32—H32B	109.5
N2—C33—C34	120.47 (13)	H32A—C32—H32C	109.5
N2—C33—C38	120.98 (13)	H32B—C32—H32C	109.5
F1—C13—C12—C11	175.88 (11)	C22—C17—C1—C8	100.06 (14)
F1—C13—C14—C15	−178.53 (11)	C8—C7—C6—C5	−0.5 (2)
F3—C18—C17—C22	178.77 (11)	C8—C9—C4—C5	−0.6 (2)
F3—C18—C17—C1	−2.05 (19)	C8—C9—C3—C2	−38.25 (18)
F3—C18—C19—F4	0.15 (19)	C7—C8—C1—N1	−147.06 (12)
F3—C18—C19—C20	179.81 (12)	C7—C8—C1—C17	88.84 (15)
F7—C40—C41—F8	0.95 (19)	C7—C8—C9—C4	−1.7 (2)
F7—C40—C41—C42	−178.75 (13)	C7—C8—C9—C3	177.54 (13)
F4—C19—C20—C21	−179.06 (14)	C31—C30—C23—N2	36.87 (16)
F8—C41—C42—C43	179.50 (13)	C31—C30—C23—C39	−89.25 (15)
F6—C35—C36—C37	178.84 (13)	C31—C30—C29—C28	0.8 (2)
F5—C37—C36—C35	178.15 (13)	C31—C26—C27—O2	−179.26 (12)
O1—C5—C6—C7	179.57 (12)	C31—C26—C27—C28	1.1 (2)
O1—C5—C4—C9	−179.14 (12)	C31—C25—C24—N2	54.31 (15)
N1—C11—C12—C13	−176.12 (12)	C40—C39—C44—C43	0.6 (2)
N1—C11—C16—C15	178.92 (12)	C40—C41—C42—C43	−0.8 (2)
N2—C23—C39—C40	167.56 (12)	C1—N1—C11—C12	176.71 (11)
N2—C23—C39—C44	−8.71 (18)	C1—N1—C11—C16	−2.32 (18)
N2—C33—C34—C35	−179.93 (13)	C1—N1—C2—C3	−21.08 (17)
N2—C33—C38—C37	179.53 (13)	C1—C17—C22—C21	−177.64 (13)
C18—C17—C22—C21	1.5 (2)	C1—C8—C7—C6	−174.66 (12)
C18—C17—C1—N1	156.02 (12)	C1—C8—C9—C4	175.29 (12)
C18—C17—C1—C8	−79.07 (15)	C1—C8—C9—C3	−5.44 (19)
C18—C19—C20—C21	1.3 (2)	C27—C26—C31—C30	−2.7 (2)
C13—C14—C15—F2	−178.66 (11)	C27—C26—C31—C25	−179.37 (12)
C13—C14—C15—C16	2.4 (2)	C33—N2—C23—C30	148.49 (12)
C11—N1—C1—C17	−72.74 (14)	C33—N2—C23—C39	−84.98 (14)
C11—N1—C1—C8	163.72 (11)	C33—N2—C24—C25	166.77 (12)
C11—N1—C2—C3	153.95 (12)	C33—C34—C35—F6	−178.25 (12)
C11—C16—C15—F2	178.36 (11)	C33—C34—C35—C36	0.4 (2)
C11—C16—C15—C14	−2.7 (2)	C33—C38—C37—F5	−178.35 (12)
C30—C23—C39—C40	−67.12 (16)	C33—C38—C37—C36	0.4 (2)
C30—C23—C39—C44	116.61 (14)	C9—C8—C7—C6	2.3 (2)
C30—C29—C28—C27	−2.3 (2)	C9—C8—C1—N1	35.99 (17)
C30—C31—C25—C24	−47.14 (16)	C9—C8—C1—C17	−88.10 (14)
C12—C13—C14—C15	0.7 (2)	C9—C3—C2—N1	50.93 (16)
C12—C11—C16—C15	−0.14 (19)	C6—C5—C4—C9	2.4 (2)
C23—N2—C33—C34	−161.45 (12)	C4—C5—C6—C7	−1.8 (2)
C23—N2—C33—C38	19.24 (19)	C4—C9—C3—C2	141.00 (13)
C23—N2—C24—C25	−16.97 (17)	C19—C18—C17—C22	−0.6 (2)
C23—C30—C29—C28	178.58 (12)	C19—C18—C17—C1	178.55 (12)
C23—C30—C31—C26	−176.16 (12)	C19—C20—C21—C22	−0.4 (2)
C23—C30—C31—C25	0.74 (18)	C24—N2—C23—C30	−27.72 (16)
C23—C39—C40—F7	2.38 (19)	C24—N2—C23—C39	98.81 (14)
C23—C39—C40—C41	−177.46 (12)	C24—N2—C33—C34	14.86 (19)
C23—C39—C44—C43	177.05 (13)	C24—N2—C33—C38	−164.45 (13)
C17—C18—C19—F4	179.56 (12)	C44—C39—C40—F7	178.86 (12)
C17—C18—C19—C20	−0.8 (2)	C44—C39—C40—C41	−1.0 (2)
C17—C22—C21—C20	−1.0 (2)	C34—C33—C38—C37	0.2 (2)
C16—C11—C12—C13	2.95 (19)	C34—C35—C36—C37	0.2 (2)
C14—C13—C12—C11	−3.4 (2)	C3—C9—C4—C5	−179.84 (13)
C29—C30—C23—N2	−140.96 (13)	C38—C33—C34—C35	−0.6 (2)
C29—C30—C23—C39	92.92 (15)	C38—C37—C36—C35	−0.6 (2)
C29—C30—C31—C26	1.73 (19)	C2—N1—C11—C12	1.58 (19)
C29—C30—C31—C25	178.63 (12)	C2—N1—C11—C16	−177.45 (12)
C29—C28—C27—O2	−178.31 (12)	C2—N1—C1—C17	102.38 (14)
C29—C28—C27—C26	1.4 (2)	C2—N1—C1—C8	−21.16 (17)
C26—C31—C25—C24	129.68 (13)	C41—C42—C43—C44	0.5 (2)
C39—C40—C41—F8	−179.20 (12)	C10—O1—C5—C6	−179.45 (12)
C39—C40—C41—C42	1.1 (2)	C10—O1—C5—C4	2.01 (19)
C39—C44—C43—C42	−0.4 (2)	C32—O2—C27—C26	1.9 (2)
C22—C17—C1—N1	−24.85 (17)	C32—O2—C27—C28	−178.41 (12)

(6-33)

Crystal data

C22H17F4NO	Z = 4
Mr = 387.36	F(000) = 800
Triclinic, P1	Dx = 1.461 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6975 (7) Å	Cell parameters from 4971 reflections
b = 13.2186 (4) Å	θ = 3.1–27.5°
c = 13.6339 (2) Å	µ = 0.12 mm^−1
α = 68.667 (14)°	T = 100 K
β = 80.428 (18)°	Irregular, clear light colourless
γ = 81.09 (2)°	0.3 × 0.2 × 0.1 mm
V = 1761.4 (2) Å^3

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	6601 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.028
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan Blessing 1995	h = −13→13
Tmin = 0.945, Tmax = 1	k = −17→17
18147 measured reflections	l = −17→17
8043 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 0.5918P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
8043 reflections	Δρmax = 0.29 e Å^−3
641 parameters	Δρmin = −0.23 e Å^−3

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
F1	0.23185 (8)	0.59769 (7)	−0.07978 (7)	0.0258 (2)
F2	−0.02012 (8)	0.40619 (7)	0.22791 (7)	0.0263 (2)
F3	0.29550 (8)	−0.03600 (7)	0.40197 (7)	0.0263 (2)
F4	0.45992 (9)	0.28622 (7)	0.48963 (7)	0.0289 (2)
O1	0.75650 (10)	−0.16546 (8)	0.11591 (8)	0.0232 (2)
N1	0.40150 (11)	0.25182 (9)	0.14688 (9)	0.0181 (2)
C1	0.37769 (13)	0.14265 (11)	0.22281 (10)	0.0169 (3)
H1	0.2932 (16)	0.1293 (13)	0.2153 (12)	0.018 (4)*
C2	0.53086 (13)	0.27412 (11)	0.09475 (12)	0.0201 (3)
H2A	0.5407 (16)	0.2737 (14)	0.0195 (14)	0.024 (4)*
H2B	0.5443 (16)	0.3496 (14)	0.0903 (13)	0.021 (4)*
C3	0.63111 (13)	0.18923 (11)	0.15582 (12)	0.0192 (3)
H3A	0.6280 (15)	0.1976 (13)	0.2255 (13)	0.019 (4)*
H3B	0.7169 (17)	0.2038 (13)	0.1154 (13)	0.023 (4)*
C4	0.69361 (13)	0.00094 (11)	0.14245 (11)	0.0188 (3)
H4	0.7828 (17)	0.0118 (13)	0.1250 (13)	0.020 (4)*
C5	0.65856 (13)	−0.09665 (11)	0.14300 (11)	0.0194 (3)
C6	0.53106 (14)	−0.11764 (12)	0.16892 (11)	0.0216 (3)
H6	0.5027 (16)	−0.1862 (14)	0.1725 (13)	0.025 (4)*
C7	0.43996 (14)	−0.04057 (12)	0.19463 (11)	0.0202 (3)
H7	0.3491 (17)	−0.0571 (14)	0.2120 (14)	0.027 (4)*
C8	0.47422 (13)	0.05656 (11)	0.19456 (10)	0.0172 (3)
C9	0.60200 (13)	0.07761 (11)	0.16655 (10)	0.0173 (3)
C10	0.72118 (17)	−0.25656 (13)	0.09738 (14)	0.0283 (3)
H10A	0.8004 (18)	−0.2939 (15)	0.0758 (14)	0.031 (5)*
H10B	0.6794 (17)	−0.3086 (15)	0.1628 (15)	0.028 (4)*
H10C	0.663 (2)	−0.2306 (16)	0.0393 (16)	0.039 (5)*
C11	0.30319 (13)	0.33405 (11)	0.12324 (11)	0.0173 (3)
C12	0.18641 (13)	0.32758 (11)	0.19015 (11)	0.0192 (3)
H12	0.1728 (17)	0.2693 (15)	0.2564 (14)	0.027 (4)*
C13	0.09163 (13)	0.41294 (12)	0.16223 (12)	0.0206 (3)
C14	0.10193 (14)	0.50569 (12)	0.07353 (12)	0.0212 (3)
H14	0.0351 (17)	0.5634 (15)	0.0570 (14)	0.027 (4)*
C15	0.21682 (14)	0.50848 (11)	0.00999 (11)	0.0197 (3)
C16	0.31748 (13)	0.42769 (11)	0.03056 (11)	0.0188 (3)
H16	0.3947 (17)	0.4355 (14)	−0.0214 (14)	0.023 (4)*
C17	0.37784 (13)	0.13472 (11)	0.33846 (11)	0.0177 (3)
C18	0.33668 (13)	0.04521 (11)	0.42344 (11)	0.0199 (3)
C19	0.33514 (14)	0.03379 (12)	0.52872 (12)	0.0236 (3)
H19	0.3053 (17)	−0.0325 (15)	0.5842 (14)	0.028 (4)*
C20	0.37750 (14)	0.11575 (13)	0.55231 (12)	0.0240 (3)
H20	0.3780 (16)	0.1119 (14)	0.6249 (15)	0.026 (4)*
C21	0.41811 (13)	0.20475 (12)	0.46859 (12)	0.0217 (3)
C22	0.41838 (13)	0.21701 (12)	0.36329 (11)	0.0195 (3)
H22	0.4438 (16)	0.2818 (14)	0.3079 (14)	0.022 (4)*
F5	1.08296 (9)	−0.09685 (7)	0.58556 (7)	0.0305 (2)
F6	1.00838 (9)	−0.23208 (7)	0.95746 (7)	0.0285 (2)
F7	0.86180 (8)	0.35375 (8)	0.45248 (6)	0.0272 (2)
F8	1.27388 (8)	0.33469 (8)	0.64546 (7)	0.0313 (2)
O2	0.44600 (9)	0.53026 (8)	0.75727 (8)	0.0227 (2)
N2	0.87765 (11)	0.14102 (9)	0.77005 (9)	0.0178 (2)
C23	0.84684 (13)	0.22671 (11)	0.67014 (10)	0.0166 (3)
H23	0.8171 (15)	0.1927 (12)	0.6259 (12)	0.015 (4)*
C24	0.84951 (14)	0.16241 (12)	0.87036 (11)	0.0202 (3)
H24A	0.7726 (18)	0.1264 (15)	0.9136 (14)	0.028 (5)*
H24B	0.9229 (17)	0.1267 (14)	0.9118 (14)	0.027 (4)*
C25	0.83199 (14)	0.28470 (11)	0.85188 (11)	0.0197 (3)
H25A	0.9161 (17)	0.3165 (14)	0.8203 (13)	0.023 (4)*
H25B	0.8075 (17)	0.2945 (14)	0.9218 (14)	0.027 (4)*
C26	0.63470 (13)	0.41581 (11)	0.79649 (11)	0.0188 (3)
H26	0.6277 (17)	0.4419 (14)	0.8575 (14)	0.028 (4)*
C27	0.53790 (13)	0.45690 (11)	0.73024 (11)	0.0181 (3)
C28	0.53820 (13)	0.42099 (11)	0.64592 (11)	0.0187 (3)
H28	0.4708 (15)	0.4456 (12)	0.6001 (12)	0.015 (4)*
C29	0.63760 (13)	0.34584 (11)	0.62704 (11)	0.0177 (3)
H29	0.6372 (16)	0.3196 (13)	0.5690 (13)	0.022 (4)*
C30	0.73581 (12)	0.30663 (11)	0.69085 (10)	0.0161 (3)
C31	0.73196 (13)	0.34010 (11)	0.77775 (10)	0.0172 (3)
C32	0.33869 (14)	0.56731 (13)	0.69741 (13)	0.0249 (3)
H32A	0.2943 (18)	0.5046 (16)	0.7050 (15)	0.031 (5)*
H32B	0.2835 (17)	0.6209 (15)	0.7251 (14)	0.029 (5)*
H32C	0.3672 (18)	0.6050 (15)	0.6231 (16)	0.031 (5)*
C33	0.93310 (12)	0.03982 (11)	0.76984 (11)	0.0177 (3)
C34	0.98210 (13)	0.02177 (12)	0.67413 (12)	0.0202 (3)
H34	0.9810 (17)	0.0786 (14)	0.6057 (14)	0.026 (4)*
C35	1.03720 (13)	−0.08104 (12)	0.67885 (12)	0.0221 (3)
C36	1.05114 (13)	−0.16891 (12)	0.77155 (12)	0.0228 (3)
H36	1.0925 (18)	−0.2392 (16)	0.7700 (14)	0.031 (5)*
C37	1.00035 (13)	−0.14825 (11)	0.86294 (11)	0.0211 (3)
C38	0.94160 (13)	−0.04897 (11)	0.86651 (11)	0.0198 (3)
H38	0.9024 (16)	−0.0446 (13)	0.9358 (14)	0.021 (4)*
C39	0.96354 (13)	0.28587 (11)	0.60818 (11)	0.0173 (3)
C40	0.96524 (13)	0.34861 (11)	0.50108 (11)	0.0192 (3)
C41	1.06568 (14)	0.40654 (12)	0.44130 (12)	0.0229 (3)
H41	1.0592 (18)	0.4500 (15)	0.3677 (15)	0.032 (5)*
C42	1.17144 (14)	0.40278 (12)	0.48994 (12)	0.0228 (3)
H42	1.2445 (18)	0.4422 (15)	0.4514 (14)	0.030 (5)*
C43	1.17122 (13)	0.33974 (12)	0.59586 (12)	0.0210 (3)
C44	1.07166 (13)	0.28047 (11)	0.65557 (11)	0.0196 (3)
H44	1.0782 (17)	0.2360 (14)	0.7299 (14)	0.027 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0281 (5)	0.0167 (4)	0.0280 (5)	−0.0008 (3)	−0.0078 (4)	−0.0011 (3)
F2	0.0173 (4)	0.0305 (5)	0.0318 (5)	−0.0006 (3)	0.0009 (3)	−0.0142 (4)
F3	0.0307 (5)	0.0231 (4)	0.0258 (4)	−0.0116 (4)	0.0015 (4)	−0.0080 (4)
F4	0.0325 (5)	0.0334 (5)	0.0280 (5)	−0.0093 (4)	−0.0043 (4)	−0.0166 (4)
O1	0.0235 (5)	0.0210 (5)	0.0276 (5)	−0.0017 (4)	0.0003 (4)	−0.0129 (4)
N1	0.0161 (5)	0.0169 (6)	0.0185 (6)	−0.0021 (4)	−0.0022 (4)	−0.0027 (4)
C1	0.0166 (6)	0.0165 (6)	0.0169 (6)	−0.0035 (5)	−0.0029 (5)	−0.0039 (5)
C2	0.0168 (6)	0.0177 (7)	0.0233 (7)	−0.0032 (5)	−0.0024 (5)	−0.0037 (5)
C3	0.0163 (6)	0.0177 (7)	0.0235 (7)	−0.0027 (5)	−0.0031 (5)	−0.0064 (5)
C4	0.0181 (7)	0.0203 (7)	0.0167 (6)	−0.0032 (5)	−0.0014 (5)	−0.0048 (5)
C5	0.0213 (7)	0.0197 (7)	0.0169 (6)	−0.0005 (5)	−0.0016 (5)	−0.0069 (5)
C6	0.0257 (7)	0.0192 (7)	0.0215 (7)	−0.0063 (6)	−0.0011 (6)	−0.0082 (6)
C7	0.0191 (7)	0.0213 (7)	0.0205 (7)	−0.0058 (5)	−0.0003 (5)	−0.0070 (5)
C8	0.0186 (6)	0.0188 (6)	0.0139 (6)	−0.0025 (5)	−0.0030 (5)	−0.0046 (5)
C9	0.0193 (6)	0.0170 (6)	0.0150 (6)	−0.0033 (5)	−0.0043 (5)	−0.0033 (5)
C10	0.0304 (8)	0.0242 (8)	0.0355 (9)	−0.0025 (7)	−0.0004 (7)	−0.0184 (7)
C11	0.0186 (6)	0.0182 (6)	0.0178 (6)	−0.0025 (5)	−0.0050 (5)	−0.0080 (5)
C12	0.0190 (7)	0.0193 (7)	0.0200 (7)	−0.0020 (5)	−0.0044 (5)	−0.0067 (5)
C13	0.0159 (6)	0.0250 (7)	0.0252 (7)	−0.0031 (5)	−0.0026 (5)	−0.0134 (6)
C14	0.0202 (7)	0.0180 (7)	0.0292 (8)	0.0011 (5)	−0.0091 (6)	−0.0112 (6)
C15	0.0262 (7)	0.0149 (6)	0.0201 (7)	−0.0035 (5)	−0.0084 (5)	−0.0057 (5)
C16	0.0199 (7)	0.0189 (7)	0.0197 (7)	−0.0035 (5)	−0.0035 (5)	−0.0082 (5)
C17	0.0150 (6)	0.0195 (6)	0.0179 (6)	0.0004 (5)	−0.0027 (5)	−0.0062 (5)
C18	0.0174 (6)	0.0193 (7)	0.0224 (7)	−0.0024 (5)	−0.0013 (5)	−0.0068 (5)
C19	0.0217 (7)	0.0241 (7)	0.0200 (7)	−0.0019 (6)	−0.0006 (5)	−0.0029 (6)
C20	0.0213 (7)	0.0310 (8)	0.0193 (7)	0.0008 (6)	−0.0028 (5)	−0.0093 (6)
C21	0.0185 (7)	0.0248 (7)	0.0249 (7)	−0.0011 (6)	−0.0047 (5)	−0.0119 (6)
C22	0.0176 (6)	0.0195 (7)	0.0206 (7)	−0.0018 (5)	−0.0025 (5)	−0.0059 (6)
F5	0.0347 (5)	0.0303 (5)	0.0293 (5)	−0.0006 (4)	0.0026 (4)	−0.0177 (4)
F6	0.0347 (5)	0.0182 (4)	0.0280 (5)	0.0033 (4)	−0.0110 (4)	−0.0016 (3)
F7	0.0206 (4)	0.0406 (5)	0.0178 (4)	−0.0052 (4)	−0.0055 (3)	−0.0049 (4)
F8	0.0213 (4)	0.0462 (6)	0.0309 (5)	−0.0116 (4)	−0.0053 (4)	−0.0146 (4)
O2	0.0193 (5)	0.0263 (5)	0.0232 (5)	0.0043 (4)	−0.0057 (4)	−0.0108 (4)
N2	0.0229 (6)	0.0154 (5)	0.0146 (5)	−0.0012 (4)	−0.0027 (4)	−0.0047 (4)
C23	0.0183 (6)	0.0177 (6)	0.0147 (6)	−0.0025 (5)	−0.0031 (5)	−0.0058 (5)
C24	0.0251 (7)	0.0207 (7)	0.0155 (6)	0.0003 (6)	−0.0059 (5)	−0.0066 (5)
C25	0.0223 (7)	0.0201 (7)	0.0200 (7)	0.0009 (5)	−0.0077 (5)	−0.0098 (5)
C26	0.0212 (7)	0.0188 (6)	0.0171 (6)	−0.0033 (5)	−0.0026 (5)	−0.0067 (5)
C27	0.0167 (6)	0.0176 (6)	0.0186 (6)	−0.0031 (5)	−0.0006 (5)	−0.0047 (5)
C28	0.0162 (6)	0.0221 (7)	0.0159 (6)	−0.0048 (5)	−0.0045 (5)	−0.0022 (5)
C29	0.0182 (6)	0.0207 (7)	0.0145 (6)	−0.0065 (5)	−0.0020 (5)	−0.0045 (5)
C30	0.0163 (6)	0.0155 (6)	0.0163 (6)	−0.0041 (5)	−0.0016 (5)	−0.0043 (5)
C31	0.0185 (6)	0.0166 (6)	0.0166 (6)	−0.0042 (5)	−0.0038 (5)	−0.0041 (5)
C32	0.0181 (7)	0.0293 (8)	0.0249 (8)	0.0028 (6)	−0.0056 (6)	−0.0075 (6)
C33	0.0153 (6)	0.0171 (6)	0.0213 (7)	−0.0027 (5)	−0.0040 (5)	−0.0062 (5)
C34	0.0200 (7)	0.0194 (7)	0.0212 (7)	−0.0024 (5)	−0.0023 (5)	−0.0069 (6)
C35	0.0186 (7)	0.0259 (7)	0.0260 (7)	−0.0037 (6)	0.0004 (5)	−0.0146 (6)
C36	0.0170 (7)	0.0197 (7)	0.0328 (8)	0.0001 (5)	−0.0049 (6)	−0.0106 (6)
C37	0.0191 (7)	0.0172 (6)	0.0249 (7)	−0.0019 (5)	−0.0085 (5)	−0.0024 (5)
C38	0.0196 (7)	0.0194 (7)	0.0203 (7)	−0.0023 (5)	−0.0044 (5)	−0.0059 (5)
C39	0.0177 (6)	0.0160 (6)	0.0187 (6)	−0.0010 (5)	−0.0022 (5)	−0.0068 (5)
C40	0.0166 (6)	0.0208 (7)	0.0202 (7)	0.0001 (5)	−0.0040 (5)	−0.0073 (5)
C41	0.0240 (7)	0.0216 (7)	0.0197 (7)	−0.0010 (6)	−0.0010 (6)	−0.0044 (6)
C42	0.0209 (7)	0.0215 (7)	0.0261 (7)	−0.0065 (6)	0.0027 (6)	−0.0090 (6)
C43	0.0172 (6)	0.0243 (7)	0.0256 (7)	−0.0019 (5)	−0.0049 (5)	−0.0126 (6)
C44	0.0199 (7)	0.0206 (7)	0.0186 (7)	−0.0015 (5)	−0.0031 (5)	−0.0072 (5)

Geometric parameters (Å, º)

F1—C15	1.3629 (16)	F5—C35	1.3623 (16)
F2—C13	1.3631 (16)	F6—C37	1.3654 (16)
F3—C18	1.3603 (16)	F7—C40	1.3623 (16)
F4—C21	1.3633 (16)	F8—C43	1.3635 (16)
O1—C5	1.3718 (17)	O2—C27	1.3736 (17)
O1—C10	1.4320 (18)	O2—C32	1.4389 (17)
N1—C1	1.4691 (17)	N2—C23	1.4691 (17)
N1—C2	1.4676 (18)	N2—C24	1.4694 (17)
N1—C11	1.3766 (18)	N2—C33	1.3776 (17)
C1—H1	0.976 (17)	C23—H23	0.985 (16)
C1—C8	1.5272 (19)	C23—C30	1.5242 (19)
C1—C17	1.5420 (18)	C23—C39	1.5346 (19)
C2—H2A	1.016 (18)	C24—H24A	1.003 (19)
C2—H2B	1.009 (17)	C24—H24B	0.999 (18)
C2—C3	1.5320 (19)	C24—C25	1.5287 (19)
C3—H3A	0.991 (17)	C25—H25A	1.014 (18)
C3—H3B	0.996 (17)	C25—H25B	0.995 (18)
C3—C9	1.5052 (19)	C25—C31	1.5103 (19)
C4—H4	0.965 (17)	C26—H26	0.998 (18)
C4—C5	1.395 (2)	C26—C27	1.4012 (19)
C4—C9	1.3867 (19)	C26—C31	1.3872 (19)
C5—C6	1.396 (2)	C27—C28	1.394 (2)
C6—H6	0.981 (18)	C28—H28	0.972 (16)
C6—C7	1.396 (2)	C28—C29	1.397 (2)
C7—H7	1.000 (18)	C29—H29	0.974 (17)
C7—C8	1.3884 (19)	C29—C30	1.3916 (19)
C8—C9	1.3995 (19)	C30—C31	1.4003 (19)
C10—H10A	0.970 (19)	C32—H32A	0.98 (2)
C10—H10B	0.992 (19)	C32—H32B	0.991 (19)
C10—H10C	1.01 (2)	C32—H32C	0.972 (19)
C11—C12	1.4133 (19)	C33—C34	1.412 (2)
C11—C16	1.4172 (19)	C33—C38	1.4156 (19)
C12—H12	0.956 (18)	C34—H34	0.962 (18)
C12—C13	1.381 (2)	C34—C35	1.378 (2)
C13—C14	1.377 (2)	C35—C36	1.382 (2)
C14—H14	0.951 (18)	C36—H36	0.972 (19)
C14—C15	1.378 (2)	C36—C37	1.378 (2)
C15—C16	1.380 (2)	C37—C38	1.379 (2)
C16—H16	0.987 (18)	C38—H38	0.986 (17)
C17—C18	1.3894 (19)	C39—C40	1.3911 (19)
C17—C22	1.3961 (19)	C39—C44	1.3963 (19)
C18—C19	1.385 (2)	C40—C41	1.384 (2)
C19—H19	0.983 (18)	C41—H41	0.966 (19)
C19—C20	1.392 (2)	C41—C42	1.389 (2)
C20—H20	0.973 (18)	C42—H42	0.975 (19)
C20—C21	1.376 (2)	C42—C43	1.380 (2)
C21—C22	1.384 (2)	C43—C44	1.385 (2)
C22—H22	0.954 (18)	C44—H44	0.977 (18)
C5—O1—C10	116.45 (11)	C27—O2—C32	116.97 (11)
C2—N1—C1	120.12 (11)	C23—N2—C24	120.45 (11)
C11—N1—C1	120.65 (11)	C33—N2—C23	119.84 (11)
C11—N1—C2	119.22 (11)	C33—N2—C24	119.71 (11)
N1—C1—H1	107.2 (9)	N2—C23—H23	108.7 (9)
N1—C1—C8	109.86 (11)	N2—C23—C30	110.59 (11)
N1—C1—C17	112.13 (11)	N2—C23—C39	111.66 (11)
C8—C1—H1	107.7 (9)	C30—C23—H23	105.8 (9)
C8—C1—C17	111.71 (11)	C30—C23—C39	111.40 (11)
C17—C1—H1	107.9 (9)	C39—C23—H23	108.5 (9)
N1—C2—H2A	110.4 (10)	N2—C24—H24A	110.3 (10)
N1—C2—H2B	108.1 (9)	N2—C24—H24B	107.2 (10)
N1—C2—C3	111.23 (11)	N2—C24—C25	111.79 (11)
H2A—C2—H2B	107.7 (13)	H24A—C24—H24B	106.5 (14)
C3—C2—H2A	108.9 (10)	C25—C24—H24A	111.0 (10)
C3—C2—H2B	110.4 (9)	C25—C24—H24B	109.8 (10)
C2—C3—H3A	107.9 (9)	C24—C25—H25A	109.5 (9)
C2—C3—H3B	108.9 (10)	C24—C25—H25B	108.3 (10)
H3A—C3—H3B	109.3 (14)	H25A—C25—H25B	107.6 (14)
C9—C3—C2	108.43 (11)	C31—C25—C24	109.34 (11)
C9—C3—H3A	112.3 (9)	C31—C25—H25A	110.3 (9)
C9—C3—H3B	110.0 (10)	C31—C25—H25B	111.8 (10)
C5—C4—H4	117.3 (10)	C27—C26—H26	116.7 (10)
C9—C4—H4	122.5 (10)	C31—C26—H26	123.1 (10)
C9—C4—C5	120.21 (13)	C31—C26—C27	120.14 (13)
O1—C5—C4	115.25 (12)	O2—C27—C26	114.95 (12)
O1—C5—C6	124.86 (13)	O2—C27—C28	124.90 (12)
C4—C5—C6	119.89 (13)	C28—C27—C26	120.13 (13)
C5—C6—H6	122.5 (10)	C27—C28—H28	122.3 (9)
C5—C6—C7	119.39 (13)	C27—C28—C29	119.16 (12)
C7—C6—H6	118.0 (10)	C29—C28—H28	118.5 (9)
C6—C7—H7	117.9 (10)	C28—C29—H29	119.3 (10)
C8—C7—C6	121.03 (13)	C30—C29—C28	121.10 (13)
C8—C7—H7	121.1 (10)	C30—C29—H29	119.6 (10)
C7—C8—C1	122.67 (12)	C29—C30—C23	122.00 (12)
C7—C8—C9	119.08 (13)	C29—C30—C31	119.21 (12)
C9—C8—C1	118.24 (12)	C31—C30—C23	118.78 (12)
C4—C9—C3	122.78 (12)	C26—C31—C25	122.75 (12)
C4—C9—C8	120.38 (12)	C26—C31—C30	120.18 (12)
C8—C9—C3	116.66 (12)	C30—C31—C25	116.95 (12)
O1—C10—H10A	105.7 (11)	O2—C32—H32A	109.6 (11)
O1—C10—H10B	111.9 (11)	O2—C32—H32B	106.7 (11)
O1—C10—H10C	110.4 (11)	O2—C32—H32C	110.0 (11)
H10A—C10—H10B	108.0 (15)	H32A—C32—H32B	112.4 (15)
H10A—C10—H10C	110.5 (16)	H32A—C32—H32C	110.1 (16)
H10B—C10—H10C	110.2 (15)	H32B—C32—H32C	107.8 (15)
N1—C11—C12	121.23 (12)	N2—C33—C34	121.26 (12)
N1—C11—C16	120.29 (12)	N2—C33—C38	120.27 (12)
C12—C11—C16	118.49 (13)	C34—C33—C38	118.47 (13)
C11—C12—H12	122.6 (11)	C33—C34—H34	122.9 (10)
C13—C12—C11	118.44 (13)	C35—C34—C33	118.68 (13)
C13—C12—H12	118.8 (11)	C35—C34—H34	118.4 (10)
F2—C13—C12	117.88 (13)	F5—C35—C34	117.71 (13)
F2—C13—C14	117.17 (13)	F5—C35—C36	117.59 (13)
C14—C13—C12	124.94 (13)	C34—C35—C36	124.69 (14)
C13—C14—H14	122.8 (11)	C35—C36—H36	121.0 (11)
C13—C14—C15	114.82 (13)	C37—C36—C35	114.72 (13)
C15—C14—H14	122.4 (11)	C37—C36—H36	124.2 (11)
F1—C15—C14	117.44 (12)	F6—C37—C36	117.90 (13)
F1—C15—C16	117.73 (13)	F6—C37—C38	117.14 (13)
C14—C15—C16	124.83 (13)	C36—C37—C38	124.96 (13)
C11—C16—H16	122.5 (10)	C33—C38—H38	123.1 (10)
C15—C16—C11	118.47 (13)	C37—C38—C33	118.43 (13)
C15—C16—H16	118.9 (10)	C37—C38—H38	118.3 (10)
C18—C17—C1	121.49 (12)	C40—C39—C23	120.75 (12)
C18—C17—C22	116.58 (13)	C40—C39—C44	116.92 (13)
C22—C17—C1	121.93 (12)	C44—C39—C23	122.33 (12)
F3—C18—C17	118.05 (12)	F7—C40—C39	118.09 (12)
F3—C18—C19	118.07 (12)	F7—C40—C41	118.18 (12)
C19—C18—C17	123.87 (13)	C41—C40—C39	123.73 (13)
C18—C19—H19	118.8 (10)	C40—C41—H41	119.1 (11)
C18—C19—C20	118.93 (14)	C40—C41—C42	118.85 (14)
C20—C19—H19	122.3 (10)	C42—C41—H41	122.0 (11)
C19—C20—H20	122.2 (10)	C41—C42—H42	122.0 (11)
C21—C20—C19	117.53 (14)	C43—C42—C41	117.82 (13)
C21—C20—H20	120.3 (10)	C43—C42—H42	120.2 (11)
F4—C21—C20	118.66 (13)	F8—C43—C42	118.97 (13)
F4—C21—C22	117.66 (13)	F8—C43—C44	117.53 (13)
C20—C21—C22	123.68 (14)	C42—C43—C44	123.50 (13)
C17—C22—H22	119.9 (10)	C39—C44—H44	121.4 (11)
C21—C22—C17	119.39 (13)	C43—C44—C39	119.15 (13)
C21—C22—H22	120.7 (10)	C43—C44—H44	119.5 (11)
F1—C15—C16—C11	−179.63 (11)	F5—C35—C36—C37	−178.60 (12)
F2—C13—C14—C15	179.87 (12)	F6—C37—C38—C33	179.31 (12)
F3—C18—C19—C20	179.68 (12)	F7—C40—C41—C42	179.51 (13)
F4—C21—C22—C17	179.17 (12)	F8—C43—C44—C39	178.37 (12)
O1—C5—C6—C7	−179.66 (13)	O2—C27—C28—C29	−179.92 (12)
N1—C1—C8—C7	−135.84 (13)	N2—C23—C30—C29	−137.52 (13)
N1—C1—C8—C9	43.52 (16)	N2—C23—C30—C31	41.50 (16)
N1—C1—C17—C18	169.19 (12)	N2—C23—C39—C40	162.99 (12)
N1—C1—C17—C22	−10.40 (18)	N2—C23—C39—C44	−17.50 (18)
N1—C2—C3—C9	56.24 (15)	N2—C24—C25—C31	54.13 (16)
N1—C11—C12—C13	179.79 (13)	N2—C33—C34—C35	179.62 (13)
N1—C11—C16—C15	−179.73 (12)	N2—C33—C38—C37	−178.56 (12)
C1—N1—C2—C3	−19.41 (17)	C23—N2—C24—C25	−19.53 (18)
C1—N1—C11—C12	18.02 (19)	C23—N2—C33—C34	11.50 (19)
C1—N1—C11—C16	−162.07 (12)	C23—N2—C33—C38	−168.24 (12)
C1—C8—C9—C3	−6.13 (18)	C23—C30—C31—C25	−6.32 (18)
C1—C8—C9—C4	178.62 (12)	C23—C30—C31—C26	177.63 (12)
C1—C17—C18—F3	−0.17 (19)	C23—C39—C40—F7	−1.55 (19)
C1—C17—C18—C19	179.81 (13)	C23—C39—C40—C41	178.08 (13)
C1—C17—C22—C21	−179.10 (12)	C23—C39—C44—C43	−177.26 (12)
C2—N1—C1—C8	−28.98 (16)	C24—N2—C23—C30	−26.97 (17)
C2—N1—C1—C17	95.86 (14)	C24—N2—C23—C39	97.68 (14)
C2—N1—C11—C12	−162.37 (13)	C24—N2—C33—C34	−168.61 (13)
C2—N1—C11—C16	17.54 (19)	C24—N2—C33—C38	11.65 (19)
C2—C3—C9—C4	131.22 (13)	C24—C25—C31—C26	134.19 (14)
C2—C3—C9—C8	−43.90 (16)	C24—C25—C31—C30	−41.75 (17)
C4—C5—C6—C7	−0.3 (2)	C26—C27—C28—C29	−1.5 (2)
C5—C4—C9—C3	−173.12 (13)	C27—C26—C31—C25	−174.04 (13)
C5—C4—C9—C8	1.8 (2)	C27—C26—C31—C30	1.8 (2)
C5—C6—C7—C8	0.1 (2)	C27—C28—C29—C30	−0.1 (2)
C6—C7—C8—C1	−179.63 (13)	C28—C29—C30—C23	−178.52 (12)
C6—C7—C8—C9	1.0 (2)	C28—C29—C30—C31	2.5 (2)
C7—C8—C9—C3	173.25 (12)	C29—C30—C31—C25	172.73 (12)
C7—C8—C9—C4	−2.0 (2)	C29—C30—C31—C26	−3.3 (2)
C8—C1—C17—C18	−66.99 (16)	C30—C23—C39—C40	−72.81 (16)
C8—C1—C17—C22	113.42 (14)	C30—C23—C39—C44	106.70 (14)
C9—C4—C5—O1	178.74 (12)	C31—C26—C27—O2	179.22 (12)
C9—C4—C5—C6	−0.6 (2)	C31—C26—C27—C28	0.7 (2)
C10—O1—C5—C4	−169.26 (13)	C32—O2—C27—C26	−174.62 (12)
C10—O1—C5—C6	10.1 (2)	C32—O2—C27—C28	3.84 (19)
C11—N1—C1—C8	150.62 (12)	C33—N2—C23—C30	152.91 (12)
C11—N1—C1—C17	−84.53 (15)	C33—N2—C23—C39	−82.43 (15)
C11—N1—C2—C3	160.98 (12)	C33—N2—C24—C25	160.59 (12)
C11—C12—C13—F2	−179.41 (12)	C33—C34—C35—F5	179.51 (12)
C11—C12—C13—C14	−0.5 (2)	C33—C34—C35—C36	−1.5 (2)
C12—C11—C16—C15	0.19 (19)	C34—C33—C38—C37	1.7 (2)
C12—C13—C14—C15	0.9 (2)	C34—C35—C36—C37	2.4 (2)
C13—C14—C15—F1	179.12 (12)	C35—C36—C37—F6	178.69 (12)
C13—C14—C15—C16	−0.8 (2)	C35—C36—C37—C38	−1.3 (2)
C14—C15—C16—C11	0.3 (2)	C36—C37—C38—C33	−0.7 (2)
C16—C11—C12—C13	−0.1 (2)	C38—C33—C34—C35	−0.6 (2)
C17—C1—C8—C7	99.07 (15)	C39—C23—C30—C29	97.68 (15)
C17—C1—C8—C9	−81.57 (15)	C39—C23—C30—C31	−83.30 (15)
C17—C18—C19—C20	−0.3 (2)	C39—C40—C41—C42	−0.1 (2)
C18—C17—C22—C21	1.3 (2)	C40—C39—C44—C43	2.3 (2)
C18—C19—C20—C21	0.4 (2)	C40—C41—C42—C43	0.8 (2)
C19—C20—C21—F4	179.92 (12)	C41—C42—C43—F8	−179.99 (13)
C19—C20—C21—C22	0.3 (2)	C41—C42—C43—C44	0.0 (2)
C20—C21—C22—C17	−1.2 (2)	C42—C43—C44—C39	−1.7 (2)
C22—C17—C18—F3	179.44 (12)	C44—C39—C40—F7	178.91 (12)
C22—C17—C18—C19	−0.6 (2)	C44—C39—C40—C41	−1.5 (2)

(6-34)

Crystal data

C22H17F4NO	F(000) = 800
Mr = 387.36	Dx = 1.448 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4216 reflections
a = 11.322 (2) Å	θ = 3.2–27.5°
b = 12.437 (2) Å	µ = 0.12 mm^−1
c = 20.012 (3) Å	T = 100 K
β = 140.922 (8)°	Plate, clear light colourless
V = 1776.3 (5) Å^3	0.41 × 0.35 × 0.16 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	3208 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.048
profile data from ω–scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan Blessing, 1995	h = −14→14
Tmin = 0.853, Tmax = 1	k = −16→16
17876 measured reflections	l = −25→25
4065 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	All H-atom parameters refined
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 1.5046P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4065 reflections	Δρmax = 0.44 e Å^−3
321 parameters	Δρmin = −0.27 e Å^−3

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
H4	0.975 (3)	0.424 (2)	0.2979 (19)	0.032 (6)*
H6	0.740 (4)	0.695 (2)	0.275 (2)	0.039 (7)*
H7	0.686 (4)	0.606 (2)	0.351 (2)	0.040 (7)*
H1	0.833 (3)	0.4235 (19)	0.4836 (19)	0.029 (6)*
H2A	0.674 (4)	0.220 (2)	0.288 (2)	0.033 (6)*
H2B	0.843 (4)	0.150 (2)	0.393 (2)	0.050 (8)*
H3A	1.064 (3)	0.2823 (18)	0.4567 (19)	0.024 (6)*
H3B	0.941 (4)	0.251 (2)	0.342 (2)	0.044 (7)*
H12	0.694 (3)	0.071 (2)	0.393 (2)	0.034 (6)*
H14	0.661 (3)	0.047 (2)	0.5826 (19)	0.033 (6)*
H16	0.775 (3)	0.335 (2)	0.5488 (18)	0.028 (6)*
H19	0.101 (4)	0.394 (2)	0.107 (2)	0.048 (8)*
H20	0.047 (4)	0.503 (2)	0.181 (2)	0.049 (8)*
H21	0.321 (4)	0.560 (2)	0.363 (2)	0.049 (8)*
H10A	0.829 (3)	0.7291 (19)	0.1424 (19)	0.028 (6)*
H10B	0.869 (3)	0.775 (2)	0.234 (2)	0.030 (6)*
H10C	0.680 (4)	0.713 (2)	0.134 (2)	0.036 (7)*
C9	0.8801 (3)	0.40316 (16)	0.35165 (15)	0.0250 (4)
C4	0.9139 (3)	0.45927 (17)	0.30745 (16)	0.0263 (4)
C5	0.8597 (3)	0.56628 (16)	0.27693 (15)	0.0248 (4)
C6	0.7781 (3)	0.61918 (17)	0.29495 (16)	0.0265 (4)
C7	0.7441 (3)	0.56275 (17)	0.33879 (16)	0.0260 (4)
C8	0.7903 (3)	0.45383 (16)	0.36537 (15)	0.0229 (4)
C1	0.7446 (3)	0.39585 (16)	0.41058 (16)	0.0240 (4)
C2	0.7947 (3)	0.22644 (17)	0.36379 (19)	0.0316 (5)
C3	0.9356 (3)	0.28674 (17)	0.38295 (19)	0.0312 (5)
C11	0.7392 (3)	0.21668 (16)	0.46096 (15)	0.0245 (4)
C12	0.6989 (3)	0.10574 (17)	0.43809 (17)	0.0287 (4)
C13	0.6734 (3)	0.04642 (17)	0.48454 (17)	0.0310 (5)
C14	0.6809 (3)	0.08791 (18)	0.55119 (17)	0.0309 (5)
C15	0.7166 (3)	0.19717 (18)	0.57030 (16)	0.0280 (4)
C16	0.7456 (3)	0.26239 (17)	0.52814 (16)	0.0253 (4)
C17	0.5451 (3)	0.42530 (16)	0.34577 (16)	0.0257 (4)
C18	0.3854 (3)	0.39344 (18)	0.24041 (17)	0.0306 (5)
C19	0.2052 (3)	0.4214 (2)	0.17995 (19)	0.0381 (6)
C20	0.1789 (3)	0.4834 (2)	0.2248 (2)	0.0403 (6)
C21	0.3300 (4)	0.5174 (2)	0.3282 (2)	0.0375 (5)
C22	0.5082 (3)	0.48812 (17)	0.38510 (18)	0.0305 (5)
C10	0.8094 (3)	0.71540 (18)	0.18142 (19)	0.0325 (5)
N1	0.7737 (3)	0.27871 (13)	0.41969 (14)	0.0263 (4)
O1	0.8924 (2)	0.61214 (12)	0.22969 (12)	0.0301 (3)
F1	0.6379 (2)	−0.06031 (11)	0.46189 (12)	0.0456 (4)
F2	0.72560 (19)	0.24338 (10)	0.63547 (10)	0.0354 (3)
F3	0.40932 (18)	0.33238 (12)	0.19587 (10)	0.0396 (3)
F4	0.65611 (19)	0.52408 (11)	0.48627 (11)	0.0399 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C9	0.0280 (10)	0.0223 (10)	0.0235 (9)	−0.0022 (8)	0.0198 (9)	−0.0023 (8)
C4	0.0306 (11)	0.0244 (10)	0.0278 (10)	−0.0006 (8)	0.0237 (10)	−0.0028 (8)
C5	0.0258 (10)	0.0241 (10)	0.0235 (9)	−0.0050 (8)	0.0188 (9)	−0.0024 (8)
C6	0.0258 (10)	0.0219 (10)	0.0286 (10)	−0.0007 (8)	0.0204 (9)	0.0005 (8)
C7	0.0240 (10)	0.0243 (10)	0.0278 (10)	0.0013 (8)	0.0196 (9)	0.0006 (8)
C8	0.0229 (9)	0.0212 (9)	0.0207 (9)	−0.0021 (7)	0.0159 (8)	−0.0012 (7)
C1	0.0268 (10)	0.0188 (9)	0.0254 (10)	0.0007 (7)	0.0201 (9)	0.0002 (8)
C2	0.0453 (13)	0.0206 (10)	0.0359 (12)	0.0003 (9)	0.0333 (12)	−0.0010 (9)
C3	0.0441 (13)	0.0243 (11)	0.0371 (12)	0.0059 (9)	0.0346 (12)	0.0030 (9)
C11	0.0218 (9)	0.0230 (10)	0.0219 (9)	0.0019 (7)	0.0152 (9)	0.0034 (7)
C12	0.0283 (10)	0.0254 (10)	0.0234 (10)	−0.0018 (8)	0.0177 (9)	−0.0007 (8)
C13	0.0301 (11)	0.0209 (10)	0.0296 (11)	−0.0026 (8)	0.0200 (10)	0.0015 (8)
C14	0.0289 (11)	0.0292 (11)	0.0277 (11)	−0.0018 (8)	0.0203 (10)	0.0044 (8)
C15	0.0233 (10)	0.0310 (11)	0.0229 (10)	0.0000 (8)	0.0162 (9)	0.0019 (8)
C16	0.0239 (10)	0.0223 (10)	0.0244 (10)	−0.0001 (8)	0.0174 (9)	0.0011 (8)
C17	0.0247 (10)	0.0231 (10)	0.0268 (10)	−0.0011 (8)	0.0193 (9)	0.0041 (8)
C18	0.0316 (11)	0.0312 (11)	0.0293 (11)	−0.0040 (9)	0.0237 (10)	0.0034 (9)
C19	0.0253 (11)	0.0407 (13)	0.0318 (12)	−0.0056 (9)	0.0179 (10)	0.0070 (10)
C20	0.0313 (12)	0.0392 (13)	0.0488 (15)	0.0054 (10)	0.0307 (12)	0.0174 (11)
C21	0.0421 (13)	0.0303 (12)	0.0524 (15)	0.0071 (10)	0.0398 (13)	0.0109 (10)
C22	0.0337 (11)	0.0266 (11)	0.0343 (11)	0.0030 (9)	0.0272 (10)	0.0055 (9)
C10	0.0336 (12)	0.0296 (12)	0.0323 (11)	−0.0011 (9)	0.0251 (11)	0.0045 (9)
N1	0.0359 (10)	0.0174 (8)	0.0312 (9)	0.0012 (7)	0.0275 (9)	0.0013 (7)
O1	0.0388 (8)	0.0250 (7)	0.0349 (8)	−0.0027 (6)	0.0307 (8)	−0.0010 (6)
F1	0.0639 (10)	0.0254 (7)	0.0484 (9)	−0.0129 (6)	0.0438 (8)	−0.0060 (6)
F2	0.0464 (8)	0.0332 (7)	0.0387 (7)	−0.0002 (6)	0.0361 (7)	0.0028 (5)
F3	0.0353 (7)	0.0489 (8)	0.0284 (7)	−0.0103 (6)	0.0232 (6)	−0.0070 (6)
F4	0.0386 (8)	0.0391 (8)	0.0399 (8)	0.0041 (6)	0.0299 (7)	−0.0059 (6)

Geometric parameters (Å, º)

C9—C4	1.393 (3)	C12—H12	0.96 (3)
C9—C8	1.393 (3)	C12—C13	1.381 (3)
C9—C3	1.507 (3)	C13—C14	1.370 (3)
C4—H4	0.95 (2)	C13—F1	1.359 (2)
C4—C5	1.392 (3)	C14—H14	0.96 (3)
C5—C6	1.391 (3)	C14—C15	1.384 (3)
C5—O1	1.378 (2)	C15—C16	1.382 (3)
C6—H6	0.99 (3)	C15—F2	1.355 (2)
C6—C7	1.391 (3)	C16—H16	0.94 (2)
C7—H7	1.01 (3)	C17—C18	1.397 (3)
C7—C8	1.400 (3)	C17—C22	1.384 (3)
C8—C1	1.528 (3)	C18—C19	1.384 (3)
C1—H1	0.99 (2)	C18—F3	1.349 (3)
C1—C17	1.539 (3)	C19—H19	0.99 (3)
C1—N1	1.473 (2)	C19—C20	1.380 (4)
C2—H2A	0.98 (3)	C20—H20	1.02 (3)
C2—H2B	1.03 (3)	C20—C21	1.374 (4)
C2—C3	1.518 (3)	C21—H21	0.95 (3)
C2—N1	1.465 (3)	C21—C22	1.390 (3)
C3—H3A	0.98 (2)	C22—F4	1.356 (3)
C3—H3B	0.98 (3)	C10—H10A	0.98 (2)
C11—C12	1.413 (3)	C10—H10B	1.00 (2)
C11—C16	1.408 (3)	C10—H10C	0.94 (3)
C11—N1	1.389 (3)	C10—O1	1.434 (3)
C4—C9—C8	120.04 (19)	C13—C12—C11	119.1 (2)
C4—C9—C3	120.92 (19)	C14—C13—C12	124.5 (2)
C8—C9—C3	119.02 (18)	F1—C13—C12	117.3 (2)
C9—C4—H4	119.6 (15)	F1—C13—C14	118.14 (19)
C5—C4—H4	119.5 (15)	C13—C14—H14	124.6 (15)
C5—C4—C9	120.87 (19)	C13—C14—C15	115.0 (2)
C6—C5—C4	119.57 (19)	C15—C14—H14	120.4 (15)
O1—C5—C4	115.81 (18)	C16—C15—C14	124.4 (2)
O1—C5—C6	124.63 (18)	F2—C15—C14	118.03 (19)
C5—C6—H6	121.3 (15)	F2—C15—C16	117.59 (19)
C5—C6—C7	119.32 (19)	C11—C16—H16	123.0 (14)
C7—C6—H6	119.4 (15)	C15—C16—H16	117.9 (14)
C6—C7—H7	115.7 (15)	C15—C16—C11	119.04 (19)
C6—C7—C8	121.55 (19)	C18—C17—C1	122.53 (19)
C8—C7—H7	122.7 (15)	C22—C17—C1	123.26 (19)
C9—C8—C7	118.53 (18)	C22—C17—C18	114.18 (19)
C9—C8—C1	122.55 (17)	C19—C18—C17	123.4 (2)
C7—C8—C1	118.91 (17)	F3—C18—C17	117.91 (19)
C8—C1—H1	107.0 (14)	F3—C18—C19	118.7 (2)
C8—C1—C17	109.79 (16)	C18—C19—H19	117.8 (16)
C17—C1—H1	107.4 (14)	C20—C19—H19	123.0 (16)
N1—C1—H1	106.7 (14)	C20—C19—C18	119.2 (2)
N1—C1—C8	113.21 (16)	C19—C20—H20	119.7 (16)
N1—C1—C17	112.35 (16)	C21—C20—H20	119.9 (16)
H2A—C2—H2B	106 (2)	C21—C20—C19	120.4 (2)
C3—C2—H2A	111.6 (14)	C20—C21—H21	124.2 (18)
C3—C2—H2B	108.6 (16)	C20—C21—C22	118.2 (2)
N1—C2—H2A	111.1 (14)	C22—C21—H21	117.6 (18)
N1—C2—H2B	108.4 (16)	C17—C22—C21	124.7 (2)
N1—C2—C3	110.49 (18)	F4—C22—C17	117.85 (19)
H3A—C3—H3B	105 (2)	F4—C22—C21	117.5 (2)
C9—C3—H3A	109.4 (14)	H10A—C10—H10B	108.3 (19)
C9—C3—H3B	111.2 (16)	H10A—C10—H10C	110 (2)
C9—C3—C2	110.63 (19)	H10B—C10—H10C	110 (2)
C2—C3—H3A	113.0 (13)	O1—C10—H10A	104.8 (14)
C2—C3—H3B	107.6 (16)	O1—C10—H10B	113.6 (14)
C16—C11—C12	117.90 (19)	O1—C10—H10C	110.3 (16)
N1—C11—C12	121.23 (19)	C2—N1—C1	119.84 (16)
N1—C11—C16	120.87 (18)	C11—N1—C1	118.93 (17)
C11—C12—H12	120.5 (15)	C11—N1—C2	119.68 (16)
C13—C12—H12	120.3 (15)	C5—O1—C10	116.63 (17)
C9—C4—C5—C6	2.8 (3)	C11—C12—C13—F1	−178.97 (19)
C9—C4—C5—O1	−177.11 (18)	C12—C11—C16—C15	1.3 (3)
C9—C8—C1—C17	−136.73 (19)	C12—C11—N1—C1	157.14 (19)
C9—C8—C1—N1	−10.3 (3)	C12—C11—N1—C2	−8.6 (3)
C4—C9—C8—C7	−3.1 (3)	C12—C13—C14—C15	0.1 (3)
C4—C9—C8—C1	178.31 (18)	C13—C14—C15—C16	−0.7 (3)
C4—C9—C3—C2	−145.1 (2)	C13—C14—C15—F2	179.92 (18)
C4—C5—C6—C7	−2.9 (3)	C14—C15—C16—C11	0.0 (3)
C4—C5—O1—C10	169.60 (18)	C16—C11—C12—C13	−1.9 (3)
C5—C6—C7—C8	0.1 (3)	C16—C11—N1—C1	−23.7 (3)
C6—C5—O1—C10	−10.3 (3)	C16—C11—N1—C2	170.58 (19)
C6—C7—C8—C9	3.0 (3)	C17—C1—N1—C2	110.1 (2)
C6—C7—C8—C1	−178.43 (18)	C17—C1—N1—C11	−55.7 (2)
C7—C8—C1—C17	44.7 (2)	C17—C18—C19—C20	−0.4 (3)
C7—C8—C1—N1	171.18 (17)	C18—C17—C22—C21	1.0 (3)
C8—C9—C4—C5	0.3 (3)	C18—C17—C22—F4	−178.79 (18)
C8—C9—C3—C2	33.5 (3)	C18—C19—C20—C21	0.3 (3)
C8—C1—C17—C18	67.4 (2)	C19—C20—C21—C22	0.4 (3)
C8—C1—C17—C22	−110.5 (2)	C20—C21—C22—C17	−1.2 (3)
C8—C1—N1—C2	−15.0 (3)	C20—C21—C22—F4	178.67 (19)
C8—C1—N1—C11	179.24 (17)	C22—C17—C18—C19	−0.2 (3)
C1—C17—C18—C19	−178.27 (19)	C22—C17—C18—F3	179.68 (18)
C1—C17—C18—F3	1.6 (3)	N1—C1—C17—C18	−59.6 (2)
C1—C17—C22—C21	179.1 (2)	N1—C1—C17—C22	122.6 (2)
C1—C17—C22—F4	−0.8 (3)	N1—C2—C3—C9	−55.7 (2)
C3—C9—C4—C5	178.9 (2)	N1—C11—C12—C13	177.27 (19)
C3—C9—C8—C7	178.25 (19)	N1—C11—C16—C15	−177.87 (18)
C3—C9—C8—C1	−0.3 (3)	O1—C5—C6—C7	176.93 (18)
C3—C2—N1—C1	48.2 (3)	F1—C13—C14—C15	−179.68 (19)
C3—C2—N1—C11	−146.16 (19)	F2—C15—C16—C11	179.35 (18)
C11—C12—C13—C14	1.3 (3)	F3—C18—C19—C20	179.66 (19)

(6-37)

Crystal data

C22H21NO	F(000) = 1344
Mr = 315.4	Dx = 1.242 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4212 reflections
a = 10.3744 (14) Å	θ = 2.5–25.0°
b = 16.379 (2) Å	µ = 0.08 mm^−1
c = 19.851 (3) Å	T = 100 K
V = 3373.2 (8) Å^3	Block, clear light colourless
Z = 8	0.2 × 0.2 × 0.1 mm

Data collection

Bruker APEX-II CCD diffractometer	2421 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.042
Absorption correction: multi-scan SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0586 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.8737. The λ/2 correction factor is 0.00150.	θmax = 25.2°, θmin = 2.1°
Tmin = 0.651, Tmax = 0.745	h = −11→12
16968 measured reflections	k = −19→19
3014 independent reflections	l = −23→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 0.9976P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3014 reflections	Δρmax = 0.18 e Å^−3
218 parameters	Δρmin = −0.19 e Å^−3

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
C9	0.45217 (13)	1.04334 (8)	0.60640 (7)	0.0180 (3)
C4	0.54887 (13)	1.09986 (8)	0.61773 (7)	0.0199 (3)
H4	0.5639	1.142	0.5858	0.024*
C5	0.62455 (12)	1.09529 (8)	0.67590 (7)	0.0189 (3)
C6	0.60074 (13)	1.03560 (8)	0.72360 (7)	0.0194 (3)
H6	0.6509	1.0329	0.7636	0.023*
C7	0.50221 (12)	0.97966 (8)	0.71219 (7)	0.0184 (3)
H7	0.4849	0.9389	0.745	0.022*
C8	0.42866 (12)	0.98214 (8)	0.65379 (7)	0.0166 (3)
C1	0.32357 (12)	0.91998 (8)	0.64046 (7)	0.0169 (3)
H1	0.2953	0.8987	0.6853	0.02*
C2	0.22484 (13)	1.03447 (9)	0.57094 (7)	0.0213 (3)
H2A	0.1997	1.0814	0.5995	0.026*
H2B	0.1663	1.033	0.5316	0.026*
C3	0.36254 (13)	1.04616 (9)	0.54678 (7)	0.0219 (3)
H3A	0.3854	1.0025	0.5144	0.026*
H3B	0.3708	1.0994	0.5236	0.026*
C11	0.08884 (13)	0.92805 (9)	0.62232 (7)	0.0194 (3)
C12	−0.02221 (14)	0.97376 (10)	0.60749 (7)	0.0250 (3)
H12	−0.0142	1.0265	0.5881	0.03*
C13	−0.14390 (14)	0.94204 (10)	0.62117 (8)	0.0305 (4)
H13	−0.2182	0.9735	0.6108	0.037*
C14	−0.15869 (14)	0.86553 (10)	0.64965 (8)	0.0314 (4)
H14	−0.2421	0.8447	0.6594	0.038*
C15	−0.04989 (14)	0.81987 (10)	0.66374 (8)	0.0279 (4)
H15	−0.0589	0.7671	0.683	0.033*
C16	0.07184 (13)	0.84996 (9)	0.65020 (7)	0.0221 (3)
H16	0.1452	0.8173	0.6599	0.026*
C17	0.37273 (12)	0.84634 (8)	0.59993 (7)	0.0176 (3)
C18	0.47875 (13)	0.80251 (9)	0.62271 (8)	0.0244 (3)
H18	0.5214	0.8192	0.6628	0.029*
C19	0.52333 (14)	0.73472 (9)	0.58778 (8)	0.0292 (4)
H19	0.5968	0.706	0.6036	0.035*
C20	0.46097 (14)	0.70897 (9)	0.52998 (8)	0.0258 (3)
H20	0.4915	0.6627	0.5059	0.031*
C21	0.35400 (14)	0.75112 (9)	0.50756 (7)	0.0237 (3)
H21	0.3097	0.7332	0.4684	0.028*
C22	0.31102 (13)	0.81953 (9)	0.54197 (7)	0.0210 (3)
H22	0.2382	0.8485	0.5256	0.025*
C10	0.78759 (15)	1.15802 (10)	0.74362 (8)	0.0333 (4)
H10A	0.7259	1.1668	0.7803	0.05*
H10B	0.8486	1.2036	0.7421	0.05*
H10C	0.8346	1.107	0.7514	0.05*
N1	0.21069 (10)	0.95880 (7)	0.60956 (6)	0.0191 (3)
O1	0.71989 (9)	1.15307 (6)	0.68098 (5)	0.0248 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C9	0.0180 (7)	0.0195 (7)	0.0165 (7)	0.0034 (6)	0.0032 (6)	−0.0006 (6)
C4	0.0212 (7)	0.0195 (7)	0.0189 (7)	0.0007 (6)	0.0034 (6)	0.0033 (6)
C5	0.0150 (7)	0.0163 (7)	0.0252 (8)	0.0005 (5)	0.0024 (6)	−0.0011 (6)
C6	0.0186 (7)	0.0202 (7)	0.0193 (7)	0.0029 (6)	−0.0024 (6)	0.0002 (6)
C7	0.0200 (7)	0.0175 (7)	0.0176 (7)	0.0011 (6)	0.0014 (6)	0.0022 (6)
C8	0.0151 (7)	0.0163 (7)	0.0186 (7)	0.0032 (5)	0.0027 (5)	−0.0009 (6)
C1	0.0154 (7)	0.0196 (7)	0.0156 (6)	0.0007 (6)	−0.0001 (5)	0.0028 (6)
C2	0.0225 (8)	0.0231 (8)	0.0183 (7)	0.0032 (6)	−0.0030 (6)	0.0018 (6)
C3	0.0238 (8)	0.0243 (8)	0.0175 (7)	−0.0003 (6)	−0.0008 (6)	0.0040 (6)
C11	0.0169 (7)	0.0248 (8)	0.0166 (7)	0.0006 (6)	0.0010 (6)	−0.0073 (6)
C12	0.0222 (8)	0.0322 (9)	0.0206 (7)	0.0052 (6)	−0.0024 (6)	−0.0061 (7)
C13	0.0168 (8)	0.0494 (11)	0.0254 (8)	0.0046 (7)	−0.0032 (6)	−0.0146 (7)
C14	0.0176 (8)	0.0450 (10)	0.0316 (9)	−0.0079 (7)	0.0034 (7)	−0.0166 (8)
C15	0.0258 (8)	0.0306 (9)	0.0272 (8)	−0.0085 (7)	0.0051 (7)	−0.0124 (7)
C16	0.0187 (7)	0.0255 (8)	0.0220 (8)	−0.0003 (6)	0.0020 (6)	−0.0073 (6)
C17	0.0149 (7)	0.0170 (7)	0.0209 (7)	−0.0028 (5)	0.0033 (6)	0.0029 (6)
C18	0.0202 (8)	0.0225 (8)	0.0303 (8)	0.0008 (6)	−0.0039 (6)	−0.0016 (7)
C19	0.0222 (8)	0.0240 (8)	0.0413 (9)	0.0051 (6)	−0.0003 (7)	−0.0002 (7)
C20	0.0267 (8)	0.0193 (8)	0.0313 (8)	−0.0007 (6)	0.0115 (7)	−0.0023 (7)
C21	0.0275 (8)	0.0239 (8)	0.0196 (7)	−0.0038 (6)	0.0045 (6)	−0.0024 (6)
C22	0.0198 (8)	0.0243 (8)	0.0190 (7)	0.0010 (6)	0.0017 (6)	0.0015 (6)
C10	0.0304 (9)	0.0301 (9)	0.0393 (9)	−0.0100 (7)	−0.0136 (7)	0.0050 (8)
N1	0.0144 (6)	0.0201 (6)	0.0227 (6)	0.0024 (5)	−0.0004 (5)	0.0020 (5)
O1	0.0208 (5)	0.0221 (5)	0.0315 (6)	−0.0061 (4)	−0.0050 (4)	0.0046 (5)

Geometric parameters (Å, º)

C9—C4	1.3835 (19)	C12—H12	0.95
C9—C8	1.3962 (19)	C12—C13	1.392 (2)
C9—C3	1.5058 (19)	C13—H13	0.95
C4—H4	0.95	C13—C14	1.383 (2)
C4—C5	1.3983 (19)	C14—H14	0.95
C5—C6	1.3833 (19)	C14—C15	1.383 (2)
C5—O1	1.3726 (16)	C15—H15	0.95
C6—H6	0.95	C15—C16	1.382 (2)
C6—C7	1.3913 (19)	C16—H16	0.95
C7—H7	0.95	C17—C18	1.3891 (19)
C7—C8	1.3885 (19)	C17—C22	1.388 (2)
C8—C1	1.5151 (18)	C18—H18	0.95
C1—H1	1	C18—C19	1.388 (2)
C1—C17	1.5369 (19)	C19—H19	0.95
C1—N1	1.4670 (16)	C19—C20	1.383 (2)
C2—H2A	0.99	C20—H20	0.95
C2—H2B	0.99	C20—C21	1.381 (2)
C2—C3	1.5190 (19)	C21—H21	0.95
C2—N1	1.4646 (18)	C21—C22	1.386 (2)
C3—H3A	0.99	C22—H22	0.95
C3—H3B	0.99	C10—H10A	0.98
C11—C12	1.405 (2)	C10—H10B	0.98
C11—C16	1.405 (2)	C10—H10C	0.98
C11—N1	1.3841 (17)	C10—O1	1.4304 (17)
C4—C9—C8	119.83 (13)	C13—C12—H12	119.9
C4—C9—C3	123.72 (12)	C12—C13—H13	119.4
C8—C9—C3	116.34 (12)	C14—C13—C12	121.23 (14)
C9—C4—H4	119.8	C14—C13—H13	119.4
C9—C4—C5	120.37 (13)	C13—C14—H14	120.6
C5—C4—H4	119.8	C15—C14—C13	118.83 (14)
C6—C5—C4	120.19 (13)	C15—C14—H14	120.6
O1—C5—C4	115.36 (12)	C14—C15—H15	119.5
O1—C5—C6	124.45 (12)	C16—C15—C14	120.91 (15)
C5—C6—H6	120.5	C16—C15—H15	119.5
C5—C6—C7	119.02 (13)	C11—C16—H16	119.5
C7—C6—H6	120.5	C15—C16—C11	121.07 (14)
C6—C7—H7	119.3	C15—C16—H16	119.5
C8—C7—C6	121.36 (13)	C18—C17—C1	119.87 (12)
C8—C7—H7	119.3	C22—C17—C1	121.94 (12)
C9—C8—C1	119.37 (12)	C22—C17—C18	118.13 (13)
C7—C8—C9	119.18 (13)	C17—C18—H18	119.5
C7—C8—C1	121.44 (12)	C19—C18—C17	120.97 (14)
C8—C1—H1	106.8	C19—C18—H18	119.5
C8—C1—C17	112.33 (10)	C18—C19—H19	119.9
C17—C1—H1	106.8	C20—C19—C18	120.16 (14)
N1—C1—C8	110.86 (11)	C20—C19—H19	119.9
N1—C1—H1	106.8	C19—C20—H20	120.3
N1—C1—C17	112.72 (11)	C21—C20—C19	119.39 (14)
H2A—C2—H2B	108	C21—C20—H20	120.3
C3—C2—H2A	109.3	C20—C21—H21	119.9
C3—C2—H2B	109.3	C20—C21—C22	120.27 (14)
N1—C2—H2A	109.3	C22—C21—H21	119.9
N1—C2—H2B	109.3	C17—C22—H22	119.5
N1—C2—C3	111.49 (11)	C21—C22—C17	121.06 (13)
C9—C3—C2	109.19 (11)	C21—C22—H22	119.5
C9—C3—H3A	109.8	H10A—C10—H10B	109.5
C9—C3—H3B	109.8	H10A—C10—H10C	109.5
C2—C3—H3A	109.8	H10B—C10—H10C	109.5
C2—C3—H3B	109.8	O1—C10—H10A	109.5
H3A—C3—H3B	108.3	O1—C10—H10B	109.5
C16—C11—C12	117.69 (13)	O1—C10—H10C	109.5
N1—C11—C12	121.10 (13)	C2—N1—C1	120.37 (11)
N1—C11—C16	121.21 (12)	C11—N1—C1	119.65 (11)
C11—C12—H12	119.9	C11—N1—C2	119.69 (11)
C13—C12—C11	120.26 (15)	C5—O1—C10	117.18 (11)
C9—C4—C5—C6	−2.0 (2)	C3—C2—N1—C1	21.05 (17)
C9—C4—C5—O1	178.22 (12)	C3—C2—N1—C11	−165.08 (12)
C9—C8—C1—C17	87.61 (15)	C11—C12—C13—C14	0.2 (2)
C9—C8—C1—N1	−39.51 (16)	C12—C11—C16—C15	−1.2 (2)
C4—C9—C8—C7	0.76 (19)	C12—C11—N1—C1	164.63 (12)
C4—C9—C8—C1	−179.28 (12)	C12—C11—N1—C2	−9.28 (19)
C4—C9—C3—C2	−132.67 (14)	C12—C13—C14—C15	−0.9 (2)
C4—C5—C6—C7	1.1 (2)	C13—C14—C15—C16	0.5 (2)
C4—C5—O1—C10	171.41 (12)	C14—C15—C16—C11	0.6 (2)
C5—C6—C7—C8	0.7 (2)	C16—C11—C12—C13	0.8 (2)
C6—C5—O1—C10	−8.40 (19)	C16—C11—N1—C1	−15.70 (19)
C6—C7—C8—C9	−1.6 (2)	C16—C11—N1—C2	170.40 (12)
C6—C7—C8—C1	178.43 (12)	C17—C1—N1—C2	−101.71 (14)
C7—C8—C1—C17	−92.43 (15)	C17—C1—N1—C11	84.42 (14)
C7—C8—C1—N1	140.44 (13)	C17—C18—C19—C20	−1.0 (2)
C8—C9—C4—C5	1.0 (2)	C18—C17—C22—C21	−0.2 (2)
C8—C9—C3—C2	43.55 (16)	C18—C19—C20—C21	−0.2 (2)
C8—C1—C17—C18	54.26 (16)	C19—C20—C21—C22	1.2 (2)
C8—C1—C17—C22	−128.47 (13)	C20—C21—C22—C17	−1.0 (2)
C8—C1—N1—C2	25.20 (16)	C22—C17—C18—C19	1.2 (2)
C8—C1—N1—C11	−148.67 (12)	N1—C1—C17—C18	−179.62 (12)
C1—C17—C18—C19	178.61 (13)	N1—C1—C17—C22	−2.34 (18)
C1—C17—C22—C21	−177.52 (12)	N1—C2—C3—C9	−55.66 (15)
C3—C9—C4—C5	177.10 (13)	N1—C11—C12—C13	−179.49 (13)
C3—C9—C8—C7	−175.62 (12)	N1—C11—C16—C15	179.10 (13)
C3—C9—C8—C1	4.34 (18)	O1—C5—C6—C7	−179.09 (12)