Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620006873/bm5125sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-2sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-3sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-4sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-5sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-6sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-7sup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-8sup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-9sup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-13sup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-16sup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-19sup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-21sup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-23sup15.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-25sup16.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-30sup17.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-31sup18.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-33sup19.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-34sup20.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620006873/bm51256-37sup21.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620006873/bm5125sup22.pdf |
CCDC references: 1540717; 1540718; 1540719; 1540720; 1540721; 1540722; 1540723; 1540724; 1540725; 1540726; 1540727; 1540728; 1540729; 1540730; 1540731; 1540732; 1540733; 1540734; 1540735; 1540736
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).
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) Å3 | 0.25 × 0.22 × 0.18 mm |
Z = 2 |
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 on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0779P)2 + 0.0363P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.22 × 0.2 × 0.18 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0647P)2 + 0.425P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.3 × 0.2 × 0.15 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0649P)2 + 0.4956P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 2 |
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 on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0866P)2 + 0.0275P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.3 × 0.22 × 0.18 mm |
Z = 8 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0457P)2 + 1.6536P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.2 × 0.2 × 0.1 mm |
Z = 8 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.35 × 0.23 × 0.2 mm |
Z = 8 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0708P)2] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | Needle, clear yellowish yellow |
Z = 4 | 0.35 × 0.25 × 0.15 mm |
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 on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.4424P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.2 × 0.2 × 0.01 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.216 | w = 1/[σ2(Fo2) + (0.1384P)2 + 0.3392P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.25 × 0.19 × 0.18 mm |
Z = 8 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0423P)2 + 3.0682P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
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 on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.087 | w = 1/[σ2(Fo2) + (0.1622P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.3 × 0.3 × 0.2 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.192 | w = 1/[σ2(Fo2) + (0.0973P)2 + 0.0745P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.2 × 0.2 × 0.1 mm |
Z = 2 |
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 on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.1042P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | Block, clear light colourless |
Z = 8 | 0.3 × 0.1 × 0.1 mm |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.090 | H-atom parameters constrained |
wR(F2) = 0.257 | w = 1/[σ2(Fo2) + (0.128P)2] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.2 × 0.2 × 0.05 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.7613P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.34 × 0.3 × 0.25 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0685P)2 + 0.5445P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0632P)2 + 0.4499P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | All H-atom parameters refined |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.5918P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.41 × 0.35 × 0.16 mm |
Z = 4 |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | All H-atom parameters refined |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0555P)2 + 1.5046P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | Block, clear light colourless |
Z = 8 | 0.2 × 0.2 × 0.1 mm |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0401P)2 + 0.9976P] where P = (Fo2 + 2Fc2)/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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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