Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011468/hb6041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011468/hb6041Isup2.hkl |
CCDC reference: 242053
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C18H16FN3 | F(000) = 1232 |
Mr = 293.34 | Dx = 1.224 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 15369 reflections |
a = 18.0843 (5) Å | θ = 0.0–24.7° |
b = 8.1980 (14) Å | µ = 0.08 mm−1 |
c = 21.4690 (12) Å | T = 293 K |
V = 3182.9 (6) Å3 | Needle, colourless |
Z = 8 | 0.40 × 0.32 × 0.06 mm |
Stoe IPDS-2 diffractometer | 1791 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.117 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
Detector resolution: 6.67 pixels mm-1 | h = −22→22 |
rotation method scans | k = −10→9 |
43476 measured reflections | l = −26→26 |
3216 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max < 0.001 |
3216 reflections | Δρmax = 0.12 e Å−3 |
398 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0088 (7) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3412 (2) | 0.5615 (5) | 0.40277 (18) | 0.0909 (11) | |
C2 | 0.29766 (18) | 0.5376 (4) | 0.45344 (18) | 0.0792 (10) | |
H2 | 0.2520 | 0.4861 | 0.4501 | 0.095* | |
C3 | 0.32353 (17) | 0.5923 (4) | 0.51020 (15) | 0.0679 (8) | |
H3 | 0.2949 | 0.5776 | 0.5457 | 0.081* | |
C4 | 0.39113 (16) | 0.6684 (3) | 0.51491 (15) | 0.0603 (7) | |
C5 | 0.43275 (19) | 0.6911 (4) | 0.46130 (16) | 0.0781 (9) | |
H5 | 0.4783 | 0.7434 | 0.4638 | 0.094* | |
C6 | 0.4075 (2) | 0.6375 (5) | 0.40480 (18) | 0.0959 (11) | |
H6 | 0.4353 | 0.6528 | 0.3688 | 0.115* | |
C7 | 0.42458 (16) | 0.7184 (4) | 0.57460 (15) | 0.0602 (8) | |
C8 | 0.43849 (16) | 0.8131 (3) | 0.67057 (16) | 0.0638 (8) | |
C9 | 0.50630 (17) | 0.7679 (4) | 0.64452 (14) | 0.0653 (8) | |
C10 | 0.57082 (18) | 0.7838 (4) | 0.67894 (17) | 0.0835 (10) | |
H10 | 0.6163 | 0.7526 | 0.6626 | 0.100* | |
C11 | 0.56518 (19) | 0.8475 (5) | 0.73818 (18) | 0.0919 (11) | |
H11 | 0.6077 | 0.8616 | 0.7619 | 0.110* | |
C12 | 0.49732 (19) | 0.8909 (4) | 0.76282 (16) | 0.0810 (10) | |
C13 | 0.43207 (17) | 0.8765 (4) | 0.72975 (17) | 0.0740 (9) | |
H13 | 0.3867 | 0.9075 | 0.7464 | 0.089* | |
C14 | 0.4949 (3) | 0.9546 (6) | 0.8252 (2) | 0.1018 (14) | |
C15 | 0.30898 (16) | 0.8288 (3) | 0.62937 (16) | 0.0670 (8) | |
H15A | 0.2888 | 0.8357 | 0.5876 | 0.080* | |
H15B | 0.3068 | 0.9371 | 0.6474 | 0.080* | |
C16 | 0.26067 (16) | 0.7175 (4) | 0.66714 (17) | 0.0720 (8) | |
H16A | 0.2815 | 0.7030 | 0.7084 | 0.086* | |
H16B | 0.2576 | 0.6114 | 0.6473 | 0.086* | |
C17 | 0.1839 (2) | 0.7928 (6) | 0.6720 (2) | 0.1055 (13) | |
H17A | 0.1879 | 0.8953 | 0.6943 | 0.127* | |
H17B | 0.1663 | 0.8171 | 0.6304 | 0.127* | |
C18 | 0.1297 (2) | 0.6926 (7) | 0.7029 (3) | 0.158 (2) | |
H18A | 0.0831 | 0.7487 | 0.7038 | 0.236* | |
H18B | 0.1456 | 0.6705 | 0.7447 | 0.236* | |
H18C | 0.1242 | 0.5917 | 0.6807 | 0.236* | |
C19 | 0.3988 (2) | 0.4066 (5) | 0.78792 (18) | 0.0909 (11) | |
C20 | 0.3320 (2) | 0.3348 (5) | 0.78398 (18) | 0.0951 (12) | |
H20 | 0.3032 | 0.3197 | 0.8194 | 0.114* | |
C21 | 0.30728 (18) | 0.2842 (4) | 0.72655 (16) | 0.0783 (9) | |
H21 | 0.2612 | 0.2346 | 0.7232 | 0.094* | |
C22 | 0.35040 (16) | 0.3062 (3) | 0.67339 (15) | 0.0617 (8) | |
C23 | 0.41843 (18) | 0.3805 (4) | 0.67997 (16) | 0.0722 (9) | |
H23 | 0.4482 | 0.3955 | 0.6451 | 0.087* | |
C24 | 0.4433 (2) | 0.4332 (5) | 0.7379 (2) | 0.0850 (10) | |
H24 | 0.4888 | 0.4849 | 0.7423 | 0.102* | |
C25 | 0.31826 (16) | 0.2571 (4) | 0.61356 (15) | 0.0604 (8) | |
C26 | 0.23740 (17) | 0.2053 (4) | 0.54360 (14) | 0.0641 (8) | |
C27 | 0.17301 (17) | 0.1892 (4) | 0.50853 (16) | 0.0743 (9) | |
H27 | 0.1276 | 0.2236 | 0.5240 | 0.089* | |
C28 | 0.1788 (2) | 0.1208 (5) | 0.45023 (17) | 0.0853 (10) | |
H28 | 0.1367 | 0.1086 | 0.4258 | 0.102* | |
C29 | 0.2480 (2) | 0.0687 (4) | 0.42705 (16) | 0.0771 (9) | |
C30 | 0.31247 (18) | 0.0856 (4) | 0.46036 (16) | 0.0721 (9) | |
H30 | 0.3580 | 0.0526 | 0.4446 | 0.087* | |
C31 | 0.30538 (15) | 0.1551 (3) | 0.51898 (15) | 0.0616 (7) | |
C32 | 0.2502 (3) | −0.0032 (5) | 0.3654 (2) | 0.0985 (13) | |
C33 | 0.43569 (15) | 0.1455 (4) | 0.55998 (16) | 0.0648 (8) | |
H33A | 0.4394 | 0.0385 | 0.5409 | 0.078* | |
H33B | 0.4564 | 0.1378 | 0.6016 | 0.078* | |
C34 | 0.48100 (15) | 0.2650 (4) | 0.52244 (17) | 0.0669 (8) | |
H34A | 0.4597 | 0.2768 | 0.4812 | 0.080* | |
H34B | 0.4802 | 0.3710 | 0.5426 | 0.080* | |
C35 | 0.55920 (17) | 0.2064 (5) | 0.5170 (2) | 0.0969 (12) | |
H35A | 0.5786 | 0.1880 | 0.5585 | 0.116* | |
H35B | 0.5591 | 0.1024 | 0.4954 | 0.116* | |
C36 | 0.6100 (2) | 0.3198 (7) | 0.4834 (3) | 0.158 (2) | |
H36A | 0.6587 | 0.2733 | 0.4819 | 0.236* | |
H36B | 0.6118 | 0.4223 | 0.5050 | 0.236* | |
H36C | 0.5922 | 0.3368 | 0.4418 | 0.236* | |
N1 | 0.49616 (14) | 0.7082 (3) | 0.58477 (12) | 0.0676 (7) | |
N2 | 0.38608 (13) | 0.7801 (3) | 0.62497 (12) | 0.0611 (6) | |
N3 | 0.4943 (2) | 1.0041 (6) | 0.8751 (2) | 0.1309 (16) | |
N4 | 0.24691 (13) | 0.2693 (3) | 0.60257 (12) | 0.0650 (7) | |
N5 | 0.35738 (13) | 0.1906 (3) | 0.56479 (12) | 0.0613 (6) | |
N6 | 0.2498 (3) | −0.0585 (6) | 0.3172 (2) | 0.1410 (15) | |
F1 | 0.31626 (15) | 0.5032 (4) | 0.34690 (13) | 0.1398 (11) | |
F2 | 0.42337 (15) | 0.4596 (4) | 0.84456 (14) | 0.1372 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.089 (3) | 0.117 (3) | 0.067 (3) | −0.018 (2) | −0.006 (2) | −0.002 (2) |
C2 | 0.067 (2) | 0.096 (3) | 0.074 (3) | −0.0098 (18) | −0.001 (2) | 0.005 (2) |
C3 | 0.0635 (19) | 0.072 (2) | 0.068 (2) | −0.0047 (15) | 0.0065 (16) | 0.0051 (17) |
C4 | 0.0628 (18) | 0.0559 (18) | 0.0621 (19) | −0.0010 (14) | 0.0053 (16) | 0.0066 (15) |
C5 | 0.071 (2) | 0.095 (2) | 0.068 (2) | −0.0126 (18) | 0.0089 (18) | 0.004 (2) |
C6 | 0.093 (3) | 0.133 (3) | 0.062 (2) | −0.022 (2) | 0.012 (2) | −0.002 (2) |
C7 | 0.0590 (19) | 0.0564 (18) | 0.065 (2) | −0.0046 (15) | 0.0097 (16) | 0.0027 (15) |
C8 | 0.0635 (19) | 0.0615 (19) | 0.067 (2) | −0.0058 (15) | 0.0093 (17) | −0.0015 (17) |
C9 | 0.058 (2) | 0.073 (2) | 0.065 (2) | −0.0064 (15) | 0.0104 (15) | −0.0016 (16) |
C10 | 0.060 (2) | 0.113 (3) | 0.077 (2) | −0.0174 (18) | 0.0088 (18) | −0.014 (2) |
C11 | 0.073 (2) | 0.125 (3) | 0.078 (2) | −0.021 (2) | 0.005 (2) | −0.017 (2) |
C12 | 0.070 (2) | 0.099 (3) | 0.074 (2) | −0.0165 (19) | 0.0116 (19) | −0.0189 (19) |
C13 | 0.071 (2) | 0.076 (2) | 0.074 (2) | −0.0082 (16) | 0.0207 (18) | −0.0089 (18) |
C14 | 0.099 (3) | 0.122 (3) | 0.085 (4) | −0.031 (3) | 0.007 (3) | −0.026 (3) |
C15 | 0.065 (2) | 0.0583 (19) | 0.078 (2) | 0.0082 (15) | 0.0058 (17) | 0.0032 (16) |
C16 | 0.0579 (18) | 0.083 (2) | 0.076 (2) | −0.0005 (16) | 0.0135 (16) | −0.0017 (19) |
C17 | 0.069 (2) | 0.156 (4) | 0.091 (3) | 0.000 (2) | 0.010 (2) | 0.004 (3) |
C18 | 0.092 (3) | 0.198 (6) | 0.183 (5) | −0.033 (3) | 0.036 (4) | 0.015 (5) |
C19 | 0.097 (3) | 0.113 (3) | 0.063 (3) | 0.014 (3) | −0.013 (2) | −0.012 (2) |
C20 | 0.088 (3) | 0.130 (3) | 0.067 (3) | 0.005 (2) | 0.008 (2) | −0.005 (2) |
C21 | 0.069 (2) | 0.098 (3) | 0.068 (2) | −0.0014 (17) | 0.0107 (18) | 0.0025 (19) |
C22 | 0.0609 (18) | 0.0591 (18) | 0.065 (2) | 0.0041 (15) | 0.0058 (16) | 0.0038 (16) |
C23 | 0.071 (2) | 0.076 (2) | 0.069 (2) | −0.0035 (17) | 0.0016 (17) | 0.0030 (18) |
C24 | 0.074 (2) | 0.091 (3) | 0.091 (3) | 0.0001 (19) | −0.012 (2) | −0.006 (2) |
C25 | 0.062 (2) | 0.0577 (18) | 0.061 (2) | −0.0029 (16) | 0.0133 (17) | 0.0030 (15) |
C26 | 0.0589 (19) | 0.069 (2) | 0.065 (2) | −0.0079 (15) | 0.0081 (15) | 0.0049 (16) |
C27 | 0.0607 (19) | 0.090 (2) | 0.072 (2) | −0.0086 (16) | 0.0056 (17) | 0.0017 (19) |
C28 | 0.076 (2) | 0.108 (3) | 0.072 (2) | −0.016 (2) | −0.0049 (19) | 0.003 (2) |
C29 | 0.089 (2) | 0.084 (2) | 0.059 (2) | −0.005 (2) | 0.0031 (19) | 0.0002 (18) |
C30 | 0.078 (2) | 0.072 (2) | 0.066 (2) | 0.0032 (16) | 0.0106 (18) | 0.0026 (17) |
C31 | 0.0617 (19) | 0.0607 (18) | 0.0626 (19) | −0.0015 (14) | 0.0081 (16) | 0.0075 (16) |
C32 | 0.110 (3) | 0.106 (3) | 0.080 (4) | 0.005 (3) | 0.000 (3) | −0.007 (3) |
C33 | 0.0559 (19) | 0.0642 (19) | 0.074 (2) | 0.0112 (14) | 0.0066 (15) | 0.0062 (16) |
C34 | 0.0583 (17) | 0.0713 (19) | 0.071 (2) | 0.0043 (15) | 0.0084 (16) | 0.0067 (17) |
C35 | 0.063 (2) | 0.116 (3) | 0.112 (3) | 0.007 (2) | 0.013 (2) | 0.012 (3) |
C36 | 0.087 (3) | 0.156 (5) | 0.230 (7) | −0.012 (3) | 0.067 (4) | 0.032 (4) |
N1 | 0.0612 (16) | 0.0771 (18) | 0.0643 (17) | −0.0045 (13) | 0.0086 (13) | −0.0026 (14) |
N2 | 0.0543 (15) | 0.0631 (14) | 0.0657 (16) | 0.0032 (12) | 0.0110 (13) | 0.0021 (13) |
N3 | 0.132 (3) | 0.164 (4) | 0.097 (4) | −0.044 (3) | 0.019 (2) | −0.049 (3) |
N4 | 0.0541 (15) | 0.0749 (16) | 0.0660 (18) | −0.0038 (13) | 0.0100 (12) | 0.0026 (14) |
N5 | 0.0544 (14) | 0.0685 (16) | 0.0610 (15) | 0.0056 (12) | 0.0079 (12) | 0.0046 (13) |
N6 | 0.180 (4) | 0.165 (4) | 0.078 (3) | 0.032 (3) | −0.015 (3) | −0.036 (3) |
F1 | 0.131 (2) | 0.215 (3) | 0.0735 (19) | −0.0524 (18) | −0.0074 (17) | −0.0214 (15) |
F2 | 0.133 (2) | 0.192 (3) | 0.086 (2) | 0.0002 (18) | −0.0240 (17) | −0.0340 (18) |
C1—C6 | 1.353 (5) | C19—C20 | 1.346 (6) |
C1—C2 | 1.357 (5) | C19—C24 | 1.359 (6) |
C1—F1 | 1.367 (5) | C19—F2 | 1.365 (5) |
C2—C3 | 1.380 (5) | C20—C21 | 1.376 (5) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.376 (4) | C21—C22 | 1.394 (4) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.388 (4) | C22—C23 | 1.380 (4) |
C4—C7 | 1.475 (4) | C22—C25 | 1.466 (4) |
C5—C6 | 1.368 (5) | C23—C24 | 1.392 (5) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—N1 | 1.315 (4) | C25—N4 | 1.316 (3) |
C7—N2 | 1.382 (4) | C25—N5 | 1.376 (4) |
C8—C13 | 1.377 (4) | C26—N4 | 1.381 (4) |
C8—N2 | 1.389 (4) | C26—C27 | 1.393 (4) |
C8—C9 | 1.398 (4) | C26—C31 | 1.400 (4) |
C9—N1 | 1.385 (4) | C27—C28 | 1.376 (5) |
C9—C10 | 1.387 (4) | C27—H27 | 0.9300 |
C10—C11 | 1.379 (5) | C28—C29 | 1.413 (5) |
C10—H10 | 0.9300 | C28—H28 | 0.9300 |
C11—C12 | 1.383 (5) | C29—C30 | 1.375 (5) |
C11—H11 | 0.9300 | C29—C32 | 1.450 (6) |
C12—C13 | 1.382 (5) | C30—C31 | 1.387 (4) |
C12—C14 | 1.438 (6) | C30—H30 | 0.9300 |
C13—H13 | 0.9300 | C31—N5 | 1.391 (4) |
C14—N3 | 1.145 (5) | C32—N6 | 1.129 (5) |
C15—N2 | 1.453 (4) | C33—N5 | 1.467 (3) |
C15—C16 | 1.501 (4) | C33—C34 | 1.511 (4) |
C15—H15A | 0.9700 | C33—H33A | 0.9700 |
C15—H15B | 0.9700 | C33—H33B | 0.9700 |
C16—C17 | 1.523 (5) | C34—C35 | 1.498 (4) |
C16—H16A | 0.9700 | C34—H34A | 0.9700 |
C16—H16B | 0.9700 | C34—H34B | 0.9700 |
C17—C18 | 1.440 (5) | C35—C36 | 1.492 (6) |
C17—H17A | 0.9700 | C35—H35A | 0.9700 |
C17—H17B | 0.9700 | C35—H35B | 0.9700 |
C18—H18A | 0.9600 | C36—H36A | 0.9600 |
C18—H18B | 0.9600 | C36—H36B | 0.9600 |
C18—H18C | 0.9600 | C36—H36C | 0.9600 |
C6—C1—C2 | 123.7 (4) | C19—C20—H20 | 120.6 |
C6—C1—F1 | 118.8 (4) | C21—C20—H20 | 120.6 |
C2—C1—F1 | 117.5 (4) | C20—C21—C22 | 120.8 (3) |
C1—C2—C3 | 117.7 (3) | C20—C21—H21 | 119.6 |
C1—C2—H2 | 121.2 | C22—C21—H21 | 119.6 |
C3—C2—H2 | 121.2 | C23—C22—C21 | 118.2 (3) |
C4—C3—C2 | 120.9 (3) | C23—C22—C25 | 124.4 (3) |
C4—C3—H3 | 119.6 | C21—C22—C25 | 117.4 (3) |
C2—C3—H3 | 119.6 | C22—C23—C24 | 121.1 (3) |
C3—C4—C5 | 118.8 (3) | C22—C23—H23 | 119.4 |
C3—C4—C7 | 123.6 (3) | C24—C23—H23 | 119.4 |
C5—C4—C7 | 117.4 (3) | C19—C24—C23 | 117.7 (3) |
C6—C5—C4 | 120.7 (3) | C19—C24—H24 | 121.2 |
C6—C5—H5 | 119.6 | C23—C24—H24 | 121.2 |
C4—C5—H5 | 119.6 | N4—C25—N5 | 113.4 (3) |
C1—C6—C5 | 118.2 (4) | N4—C25—C22 | 121.7 (3) |
C1—C6—H6 | 120.9 | N5—C25—C22 | 124.9 (3) |
C5—C6—H6 | 120.9 | N4—C26—C27 | 129.5 (3) |
N1—C7—N2 | 112.9 (3) | N4—C26—C31 | 110.4 (3) |
N1—C7—C4 | 122.0 (3) | C27—C26—C31 | 120.1 (3) |
N2—C7—C4 | 125.1 (3) | C28—C27—C26 | 117.8 (3) |
C13—C8—N2 | 131.8 (3) | C28—C27—H27 | 121.1 |
C13—C8—C9 | 122.9 (3) | C26—C27—H27 | 121.1 |
N2—C8—C9 | 105.4 (3) | C27—C28—C29 | 120.7 (3) |
N1—C9—C10 | 129.6 (3) | C27—C28—H28 | 119.6 |
N1—C9—C8 | 110.4 (3) | C29—C28—H28 | 119.6 |
C10—C9—C8 | 120.0 (3) | C30—C29—C28 | 122.5 (3) |
C11—C10—C9 | 117.7 (3) | C30—C29—C32 | 119.5 (4) |
C11—C10—H10 | 121.2 | C28—C29—C32 | 118.0 (4) |
C9—C10—H10 | 121.2 | C29—C30—C31 | 115.8 (3) |
C10—C11—C12 | 121.1 (3) | C29—C30—H30 | 122.1 |
C10—C11—H11 | 119.5 | C31—C30—H30 | 122.1 |
C12—C11—H11 | 119.5 | C30—C31—N5 | 131.7 (3) |
C13—C12—C11 | 122.6 (3) | C30—C31—C26 | 123.0 (3) |
C13—C12—C14 | 118.9 (3) | N5—C31—C26 | 105.4 (3) |
C11—C12—C14 | 118.5 (3) | N6—C32—C29 | 178.0 (6) |
C8—C13—C12 | 115.7 (3) | N5—C33—C34 | 113.4 (2) |
C8—C13—H13 | 122.1 | N5—C33—H33A | 108.9 |
C12—C13—H13 | 122.1 | C34—C33—H33A | 108.9 |
N3—C14—C12 | 178.6 (6) | N5—C33—H33B | 108.9 |
N2—C15—C16 | 115.3 (2) | C34—C33—H33B | 108.9 |
N2—C15—H15A | 108.5 | H33A—C33—H33B | 107.7 |
C16—C15—H15A | 108.5 | C35—C34—C33 | 110.2 (3) |
N2—C15—H15B | 108.5 | C35—C34—H34A | 109.6 |
C16—C15—H15B | 108.5 | C33—C34—H34A | 109.6 |
H15A—C15—H15B | 107.5 | C35—C34—H34B | 109.6 |
C15—C16—C17 | 108.7 (3) | C33—C34—H34B | 109.6 |
C15—C16—H16A | 109.9 | H34A—C34—H34B | 108.1 |
C17—C16—H16A | 109.9 | C36—C35—C34 | 114.8 (4) |
C15—C16—H16B | 109.9 | C36—C35—H35A | 108.6 |
C17—C16—H16B | 109.9 | C34—C35—H35A | 108.6 |
H16A—C16—H16B | 108.3 | C36—C35—H35B | 108.6 |
C18—C17—C16 | 114.9 (4) | C34—C35—H35B | 108.6 |
C18—C17—H17A | 108.5 | H35A—C35—H35B | 107.6 |
C16—C17—H17A | 108.5 | C35—C36—H36A | 109.5 |
C18—C17—H17B | 108.5 | C35—C36—H36B | 109.5 |
C16—C17—H17B | 108.5 | H36A—C36—H36B | 109.5 |
H17A—C17—H17B | 107.5 | C35—C36—H36C | 109.5 |
C17—C18—H18A | 109.5 | H36A—C36—H36C | 109.5 |
C17—C18—H18B | 109.5 | H36B—C36—H36C | 109.5 |
H18A—C18—H18B | 109.5 | C7—N1—C9 | 105.2 (3) |
C17—C18—H18C | 109.5 | C7—N2—C8 | 106.2 (2) |
H18A—C18—H18C | 109.5 | C7—N2—C15 | 129.4 (3) |
H18B—C18—H18C | 109.5 | C8—N2—C15 | 123.7 (3) |
C20—C19—C24 | 123.5 (4) | C25—N4—C26 | 104.9 (3) |
C20—C19—F2 | 119.1 (4) | C25—N5—C31 | 105.9 (2) |
C24—C19—F2 | 117.4 (4) | C25—N5—C33 | 130.5 (3) |
C19—C20—C21 | 118.7 (4) | C31—N5—C33 | 123.3 (3) |