The title compound, C
30H
26ClN
3, crystallizes with
Z' = 3 in the
P space group. The three independent molecules have very similar, although not identical, conformations, with almost perfect screw-boat forms adopted by the non-aromatic carbocyclic rings. Four independent C-H
(arene) hydrogen bonds link the molecules into centrosymmetric six-component aggregates.
Supporting information
CCDC reference: 665504
Equimolar quantities (1 mmol of each component) of 5-amino-3-tert-butyl-1-phenylpyrazole and 2-(4-chlorobenzylidene)-1-tetralone were thoroughly mixed at room temperature. The mixture was heated in an oil-bath at 423 K for 3.5 min, stirred briefly, and then allowed to cool to ambient temperature at which point it solidified. The solid was extracted with ethanol and, after removal of the solvent from the extract, the product (I) was recrystallized from ethanol–dimethylformamide (1:1 v/v) to give yellow crystals suitable for single-crystal X-ray diffraction (yield 72%, m.p. 468–470 K).
Crystals of compound (I) are triclinic; space group P1 was selected and confirmed by the structure analysis. All H atoms were located in difference maps and then treated as riding atoms in geometrically idealized positions, with C—H distances of 0.95 Å (aromatic), 0.98 Å (CH3) or 0.99 Å (CH2) and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups and 1.2 for all other H atoms. Examination of the refined structure using the ADDSYM option in PLATON (Spek, 2003) revealed no additional symmetry.
Data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005) and WinGX (Farrugia, 1999); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
8-
tert-Butyl-7-(4-chlorophenyl)-10-phenyl-5,6-dihydro-10
H- benzo[
h]pyrazolo[3,4-
b]quinoline
top
Crystal data top
C30H26ClN3 | Z = 6 |
Mr = 463.99 | F(000) = 1464 |
Triclinic, P1 | Dx = 1.275 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1170 (18) Å | Cell parameters from 16583 reflections |
b = 15.948 (3) Å | θ = 3.1–27.5° |
c = 17.717 (2) Å | µ = 0.18 mm−1 |
α = 93.750 (11)° | T = 120 K |
β = 91.803 (9)° | Block, yellow |
γ = 101.155 (13)° | 0.57 × 0.32 × 0.19 mm |
V = 3624.7 (10) Å3 | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 16583 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 8207 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −20→20 |
Tmin = 0.904, Tmax = 0.966 | l = −22→23 |
87246 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0984P)2 + 1.4848P] where P = (Fo2 + 2Fc2)/3 |
16583 reflections | (Δ/σ)max < 0.001 |
928 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
Crystal data top
C30H26ClN3 | γ = 101.155 (13)° |
Mr = 463.99 | V = 3624.7 (10) Å3 |
Triclinic, P1 | Z = 6 |
a = 13.1170 (18) Å | Mo Kα radiation |
b = 15.948 (3) Å | µ = 0.18 mm−1 |
c = 17.717 (2) Å | T = 120 K |
α = 93.750 (11)° | 0.57 × 0.32 × 0.19 mm |
β = 91.803 (9)° | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 16583 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 8207 reflections with I > 2σ(I) |
Tmin = 0.904, Tmax = 0.966 | Rint = 0.074 |
87246 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.53 e Å−3 |
16583 reflections | Δρmin = −0.50 e Å−3 |
928 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C11 | 0.2842 (2) | 0.28521 (19) | 0.26343 (17) | 0.0336 (7) | |
C11A | 0.3019 (2) | 0.39781 (18) | 0.17080 (16) | 0.0278 (7) | |
C11B | 0.2973 (2) | 0.37154 (18) | 0.24913 (16) | 0.0296 (7) | |
C12 | 0.2804 (3) | 0.2614 (2) | 0.33720 (17) | 0.0371 (8) | |
C13 | 0.2897 (3) | 0.3224 (2) | 0.39680 (17) | 0.0418 (8) | |
C14 | 0.3036 (3) | 0.4079 (2) | 0.38313 (18) | 0.0416 (8) | |
C14A | 0.3080 (3) | 0.4331 (2) | 0.30955 (17) | 0.0377 (8) | |
C15 | 0.3288 (3) | 0.5256 (2) | 0.29332 (19) | 0.0553 (10) | |
C16 | 0.2801 (3) | 0.5420 (2) | 0.22150 (18) | 0.0416 (8) | |
C16A | 0.2967 (2) | 0.48331 (18) | 0.15563 (16) | 0.0302 (7) | |
C17 | 0.3039 (2) | 0.50883 (18) | 0.08181 (16) | 0.0289 (7) | |
C171 | 0.2987 (2) | 0.59974 (18) | 0.06959 (16) | 0.0293 (7) | |
C172 | 0.2035 (3) | 0.6225 (2) | 0.0572 (2) | 0.0459 (9) | |
C173 | 0.1970 (3) | 0.7072 (2) | 0.0471 (2) | 0.0467 (9) | |
C174 | 0.2856 (3) | 0.76843 (18) | 0.04960 (17) | 0.0339 (7) | |
Cl17 | 0.27739 (7) | 0.87348 (5) | 0.03488 (5) | 0.0477 (2) | |
C175 | 0.3811 (3) | 0.74815 (19) | 0.06426 (18) | 0.0402 (8) | |
C176 | 0.3869 (2) | 0.66339 (19) | 0.07374 (18) | 0.0366 (8) | |
C17A | 0.3174 (2) | 0.44704 (17) | 0.02394 (16) | 0.0270 (6) | |
C18 | 0.3305 (2) | 0.43850 (18) | −0.05703 (16) | 0.0299 (7) | |
C181 | 0.3366 (2) | 0.50077 (18) | −0.11905 (16) | 0.0327 (7) | |
C182 | 0.4315 (3) | 0.5727 (2) | −0.1027 (2) | 0.0506 (10) | |
C183 | 0.2389 (3) | 0.5377 (2) | −0.1267 (2) | 0.0558 (10) | |
C184 | 0.3511 (4) | 0.4549 (2) | −0.19492 (19) | 0.0674 (13) | |
N19 | 0.34144 (19) | 0.35993 (15) | −0.07791 (13) | 0.0301 (6) | |
N110 | 0.33591 (19) | 0.31392 (14) | −0.01506 (12) | 0.0275 (6) | |
C101 | 0.3492 (2) | 0.22776 (17) | −0.02256 (16) | 0.0280 (7) | |
C102 | 0.3824 (2) | 0.18890 (19) | 0.03879 (17) | 0.0337 (7) | |
C103 | 0.3977 (3) | 0.10535 (19) | 0.02867 (17) | 0.0357 (8) | |
C104 | 0.3826 (3) | 0.06150 (19) | −0.04139 (17) | 0.0369 (8) | |
C105 | 0.3493 (3) | 0.10065 (18) | −0.10236 (17) | 0.0363 (8) | |
C106 | 0.3323 (2) | 0.18357 (18) | −0.09318 (17) | 0.0335 (7) | |
C10A | 0.3209 (2) | 0.36435 (18) | 0.04747 (15) | 0.0265 (6) | |
N111 | 0.31324 (18) | 0.33805 (14) | 0.11708 (13) | 0.0270 (5) | |
C21 | 0.0508 (2) | 0.3494 (2) | 0.05326 (17) | 0.0345 (7) | |
C21A | 0.0368 (2) | 0.24276 (19) | 0.15120 (16) | 0.0303 (7) | |
C21B | 0.0508 (2) | 0.2662 (2) | 0.07218 (16) | 0.0320 (7) | |
C22 | 0.0657 (2) | 0.3717 (2) | −0.02016 (18) | 0.0396 (8) | |
C23 | 0.0800 (3) | 0.3101 (2) | −0.07592 (18) | 0.0427 (8) | |
C24 | 0.0806 (3) | 0.2277 (2) | −0.05726 (18) | 0.0441 (9) | |
C24A | 0.0676 (2) | 0.2041 (2) | 0.01688 (17) | 0.0371 (8) | |
C25 | 0.0745 (3) | 0.1176 (2) | 0.03925 (19) | 0.0489 (9) | |
C26 | 0.0091 (3) | 0.0894 (2) | 0.10276 (18) | 0.0456 (9) | |
C26A | 0.0193 (2) | 0.15527 (19) | 0.16810 (17) | 0.0333 (7) | |
C27 | 0.0060 (2) | 0.13368 (18) | 0.24289 (17) | 0.0304 (7) | |
C271 | −0.0231 (2) | 0.04111 (18) | 0.25685 (16) | 0.0310 (7) | |
C272 | −0.1277 (2) | 0.00160 (19) | 0.25123 (17) | 0.0339 (7) | |
C273 | −0.1587 (2) | −0.08543 (18) | 0.26001 (17) | 0.0336 (7) | |
C274 | −0.0842 (2) | −0.13339 (18) | 0.27303 (16) | 0.0307 (7) | |
Cl27 | −0.12306 (7) | −0.24287 (5) | 0.28226 (5) | 0.0448 (2) | |
C275 | 0.0203 (3) | −0.0964 (2) | 0.27831 (18) | 0.0387 (8) | |
C276 | 0.0498 (3) | −0.00897 (19) | 0.26999 (17) | 0.0358 (7) | |
C27A | 0.0136 (2) | 0.20129 (17) | 0.29989 (16) | 0.0265 (6) | |
C28 | 0.0076 (2) | 0.21547 (18) | 0.38099 (16) | 0.0292 (7) | |
C281 | −0.0008 (2) | 0.15638 (18) | 0.44531 (16) | 0.0323 (7) | |
C282 | 0.0961 (3) | 0.1165 (2) | 0.45083 (19) | 0.0450 (9) | |
C283 | −0.0986 (3) | 0.0869 (2) | 0.4353 (2) | 0.0449 (9) | |
C284 | −0.0065 (3) | 0.2082 (2) | 0.52018 (18) | 0.0499 (10) | |
N29 | 0.0140 (2) | 0.29819 (15) | 0.40004 (13) | 0.0312 (6) | |
N210 | 0.02456 (19) | 0.34045 (14) | 0.33484 (13) | 0.0288 (6) | |
C201 | 0.0258 (2) | 0.42974 (18) | 0.33871 (17) | 0.0298 (7) | |
C202 | −0.0126 (2) | 0.46670 (18) | 0.27823 (17) | 0.0342 (7) | |
C203 | −0.0134 (3) | 0.55394 (19) | 0.28436 (18) | 0.0406 (8) | |
C204 | 0.0215 (3) | 0.60284 (19) | 0.35049 (18) | 0.0417 (8) | |
C205 | 0.0590 (3) | 0.56554 (19) | 0.41036 (19) | 0.0447 (9) | |
C206 | 0.0626 (3) | 0.47911 (19) | 0.40486 (18) | 0.0390 (8) | |
C20A | 0.0263 (2) | 0.28428 (18) | 0.27356 (16) | 0.0286 (7) | |
N211 | 0.03805 (19) | 0.30737 (15) | 0.20312 (13) | 0.0293 (6) | |
C31 | 0.6352 (3) | −0.0144 (2) | 0.63928 (18) | 0.0376 (8) | |
C31A | 0.6558 (2) | 0.09495 (18) | 0.54326 (17) | 0.0318 (7) | |
C31B | 0.6647 (2) | 0.07042 (19) | 0.62183 (17) | 0.0316 (7) | |
C32 | 0.6439 (3) | −0.0367 (2) | 0.71302 (19) | 0.0420 (8) | |
C33 | 0.6829 (3) | 0.0256 (2) | 0.77036 (19) | 0.0406 (8) | |
C34 | 0.7133 (3) | 0.1098 (2) | 0.75361 (18) | 0.0400 (8) | |
C34A | 0.7055 (2) | 0.13333 (19) | 0.67987 (18) | 0.0362 (7) | |
C35 | 0.7414 (3) | 0.2229 (2) | 0.65938 (19) | 0.0492 (9) | |
C36 | 0.6841 (3) | 0.2475 (2) | 0.59451 (18) | 0.0436 (8) | |
C36A | 0.6671 (2) | 0.18215 (19) | 0.52864 (17) | 0.0343 (7) | |
C37 | 0.6599 (2) | 0.20524 (18) | 0.45423 (17) | 0.0303 (7) | |
C371 | 0.6687 (3) | 0.29774 (19) | 0.44063 (17) | 0.0342 (7) | |
C372 | 0.5829 (3) | 0.3363 (2) | 0.4466 (2) | 0.0482 (9) | |
C373 | 0.5907 (3) | 0.4225 (2) | 0.4349 (2) | 0.0523 (10) | |
C374 | 0.6858 (3) | 0.47029 (19) | 0.41840 (17) | 0.0411 (9) | |
Cl37 | 0.69703 (10) | 0.57825 (5) | 0.40401 (5) | 0.0657 (3) | |
C375 | 0.7719 (3) | 0.43434 (19) | 0.41418 (17) | 0.0391 (8) | |
C376 | 0.7631 (3) | 0.34802 (18) | 0.42517 (16) | 0.0323 (7) | |
C37A | 0.6435 (2) | 0.13884 (18) | 0.39540 (17) | 0.0300 (7) | |
C38 | 0.6352 (2) | 0.12695 (18) | 0.31329 (17) | 0.0312 (7) | |
C381 | 0.6452 (3) | 0.18850 (18) | 0.25007 (17) | 0.0353 (7) | |
C382 | 0.7568 (3) | 0.2369 (2) | 0.24799 (19) | 0.0412 (8) | |
C383 | 0.5722 (3) | 0.2525 (2) | 0.2613 (2) | 0.0525 (10) | |
C384 | 0.6164 (3) | 0.1374 (2) | 0.17421 (19) | 0.0543 (10) | |
N39 | 0.6202 (2) | 0.04405 (15) | 0.29159 (14) | 0.0329 (6) | |
N310 | 0.61851 (19) | −0.00013 (15) | 0.35535 (14) | 0.0317 (6) | |
C301 | 0.6022 (2) | −0.09084 (17) | 0.34717 (17) | 0.0305 (7) | |
C302 | 0.6421 (3) | −0.13599 (19) | 0.40131 (18) | 0.0406 (8) | |
C303 | 0.6289 (3) | −0.2242 (2) | 0.3898 (2) | 0.0474 (9) | |
C304 | 0.5778 (3) | −0.2671 (2) | 0.32496 (19) | 0.0431 (8) | |
C305 | 0.5379 (3) | −0.22144 (19) | 0.27190 (18) | 0.0377 (8) | |
C306 | 0.5486 (2) | −0.13372 (19) | 0.28295 (17) | 0.0327 (7) | |
C30A | 0.6332 (2) | 0.05518 (18) | 0.41896 (17) | 0.0310 (7) | |
N311 | 0.63699 (19) | 0.03055 (15) | 0.48924 (14) | 0.0307 (6) | |
H11 | 0.2779 | 0.2427 | 0.2225 | 0.040* | |
H12 | 0.2714 | 0.2026 | 0.3467 | 0.045* | |
H13 | 0.2865 | 0.3057 | 0.4473 | 0.050* | |
H14 | 0.3104 | 0.4499 | 0.4244 | 0.050* | |
H15A | 0.3030 | 0.5590 | 0.3351 | 0.066* | |
H15B | 0.4049 | 0.5462 | 0.2922 | 0.066* | |
H16A | 0.3081 | 0.6018 | 0.2101 | 0.050* | |
H16B | 0.2044 | 0.5366 | 0.2277 | 0.050* | |
H172 | 0.1418 | 0.5799 | 0.0556 | 0.055* | |
H173 | 0.1312 | 0.7222 | 0.0385 | 0.056* | |
H175 | 0.4424 | 0.7915 | 0.0679 | 0.048* | |
H176 | 0.4528 | 0.6489 | 0.0833 | 0.044* | |
H18A | 0.4207 | 0.6082 | −0.0576 | 0.076* | |
H18B | 0.4415 | 0.6081 | −0.1461 | 0.076* | |
H18C | 0.4933 | 0.5479 | −0.0941 | 0.076* | |
H18D | 0.1781 | 0.4909 | −0.1340 | 0.084* | |
H18E | 0.2433 | 0.5727 | −0.1704 | 0.084* | |
H18F | 0.2321 | 0.5734 | −0.0807 | 0.084* | |
H18G | 0.2944 | 0.4051 | −0.2051 | 0.101* | |
H18H | 0.4178 | 0.4360 | −0.1934 | 0.101* | |
H18I | 0.3502 | 0.4942 | −0.2351 | 0.101* | |
H102 | 0.3946 | 0.2191 | 0.0872 | 0.040* | |
H103 | 0.4189 | 0.0780 | 0.0708 | 0.043* | |
H104 | 0.3949 | 0.0048 | −0.0479 | 0.044* | |
H105 | 0.3381 | 0.0704 | −0.1508 | 0.044* | |
H106 | 0.3091 | 0.2101 | −0.1352 | 0.040* | |
H21 | 0.0404 | 0.3914 | 0.0913 | 0.041* | |
H22 | 0.0662 | 0.4289 | −0.0325 | 0.047* | |
H23 | 0.0893 | 0.3248 | −0.1267 | 0.051* | |
H24 | 0.0900 | 0.1859 | −0.0958 | 0.053* | |
H25A | 0.0536 | 0.0760 | −0.0051 | 0.059* | |
H25B | 0.1478 | 0.1169 | 0.0537 | 0.059* | |
H26A | 0.0283 | 0.0368 | 0.1207 | 0.055* | |
H26B | −0.0646 | 0.0747 | 0.0841 | 0.055* | |
H272 | −0.1788 | 0.0347 | 0.2412 | 0.041* | |
H273 | −0.2304 | −0.1115 | 0.2571 | 0.040* | |
H275 | 0.0711 | −0.1301 | 0.2874 | 0.046* | |
H276 | 0.1215 | 0.0169 | 0.2734 | 0.043* | |
H28A | 0.1020 | 0.0829 | 0.4034 | 0.067* | |
H28B | 0.0904 | 0.0790 | 0.4928 | 0.067* | |
H28C | 0.1580 | 0.1620 | 0.4598 | 0.067* | |
H28D | −0.1581 | 0.1127 | 0.4217 | 0.067* | |
H28E | −0.1112 | 0.0591 | 0.4828 | 0.067* | |
H28F | −0.0896 | 0.0443 | 0.3950 | 0.067* | |
H28G | 0.0558 | 0.2534 | 0.5282 | 0.075* | |
H28H | −0.0107 | 0.1703 | 0.5618 | 0.075* | |
H28I | −0.0684 | 0.2341 | 0.5185 | 0.075* | |
H202 | −0.0381 | 0.4329 | 0.2330 | 0.041* | |
H203 | −0.0383 | 0.5800 | 0.2427 | 0.049* | |
H204 | 0.0196 | 0.6622 | 0.3546 | 0.050* | |
H205 | 0.0827 | 0.5993 | 0.4560 | 0.054* | |
H206 | 0.0900 | 0.4539 | 0.4461 | 0.047* | |
H31 | 0.6089 | −0.0575 | 0.6002 | 0.045* | |
H32 | 0.6231 | −0.0948 | 0.7244 | 0.050* | |
H33 | 0.6886 | 0.0104 | 0.8210 | 0.049* | |
H34 | 0.7399 | 0.1524 | 0.7931 | 0.048* | |
H35A | 0.7357 | 0.2623 | 0.7039 | 0.059* | |
H35B | 0.8159 | 0.2307 | 0.6479 | 0.059* | |
H36A | 0.7230 | 0.3022 | 0.5779 | 0.052* | |
H36B | 0.6157 | 0.2572 | 0.6110 | 0.052* | |
H372 | 0.5179 | 0.3034 | 0.4588 | 0.058* | |
H373 | 0.5314 | 0.4484 | 0.4383 | 0.063* | |
H375 | 0.8373 | 0.4681 | 0.4038 | 0.047* | |
H376 | 0.8229 | 0.3229 | 0.4220 | 0.039* | |
H38A | 0.7627 | 0.2748 | 0.2063 | 0.062* | |
H38B | 0.8031 | 0.1959 | 0.2403 | 0.062* | |
H38C | 0.7766 | 0.2711 | 0.2960 | 0.062* | |
H38D | 0.5024 | 0.2215 | 0.2711 | 0.079* | |
H38E | 0.5692 | 0.2834 | 0.2155 | 0.079* | |
H38F | 0.5985 | 0.2934 | 0.3045 | 0.079* | |
H38G | 0.6175 | 0.1769 | 0.1340 | 0.081* | |
H38H | 0.5465 | 0.1023 | 0.1757 | 0.081* | |
H38I | 0.6665 | 0.1003 | 0.1642 | 0.081* | |
H302 | 0.6781 | −0.1068 | 0.4458 | 0.049* | |
H303 | 0.6554 | −0.2557 | 0.4270 | 0.057* | |
H304 | 0.5703 | −0.3275 | 0.3171 | 0.052* | |
H305 | 0.5026 | −0.2506 | 0.2272 | 0.045* | |
H306 | 0.5194 | −0.1028 | 0.2467 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.0397 (19) | 0.0341 (18) | 0.0287 (17) | 0.0109 (14) | 0.0024 (14) | 0.0029 (14) |
C11A | 0.0266 (16) | 0.0296 (16) | 0.0250 (16) | 0.0013 (13) | 0.0010 (12) | −0.0007 (13) |
C11B | 0.0283 (17) | 0.0325 (17) | 0.0265 (16) | 0.0024 (13) | 0.0031 (13) | 0.0004 (13) |
C12 | 0.046 (2) | 0.0355 (18) | 0.0319 (18) | 0.0110 (15) | 0.0047 (15) | 0.0077 (15) |
C13 | 0.051 (2) | 0.055 (2) | 0.0214 (17) | 0.0134 (17) | 0.0061 (15) | 0.0080 (15) |
C14 | 0.055 (2) | 0.043 (2) | 0.0256 (18) | 0.0074 (17) | 0.0034 (15) | −0.0032 (15) |
C14A | 0.042 (2) | 0.0379 (18) | 0.0312 (18) | 0.0041 (15) | 0.0040 (14) | −0.0009 (15) |
C15 | 0.096 (3) | 0.0333 (19) | 0.032 (2) | 0.0043 (19) | 0.0091 (19) | −0.0048 (15) |
C16 | 0.055 (2) | 0.0314 (18) | 0.038 (2) | 0.0095 (16) | 0.0060 (16) | 0.0009 (15) |
C16A | 0.0349 (18) | 0.0249 (16) | 0.0298 (17) | 0.0047 (13) | 0.0035 (13) | −0.0021 (13) |
C17 | 0.0287 (17) | 0.0270 (16) | 0.0299 (17) | 0.0022 (13) | 0.0012 (13) | 0.0029 (13) |
C171 | 0.0352 (18) | 0.0245 (15) | 0.0264 (16) | 0.0014 (13) | 0.0024 (13) | 0.0017 (12) |
C172 | 0.039 (2) | 0.0312 (18) | 0.064 (2) | 0.0013 (15) | −0.0036 (17) | 0.0021 (17) |
C173 | 0.041 (2) | 0.0329 (19) | 0.066 (2) | 0.0082 (16) | −0.0082 (18) | 0.0032 (17) |
C174 | 0.047 (2) | 0.0239 (16) | 0.0297 (17) | 0.0033 (14) | 0.0036 (14) | 0.0014 (13) |
Cl17 | 0.0701 (6) | 0.0273 (4) | 0.0466 (5) | 0.0103 (4) | 0.0058 (4) | 0.0071 (4) |
C175 | 0.039 (2) | 0.0284 (17) | 0.049 (2) | −0.0037 (15) | 0.0060 (16) | 0.0004 (15) |
C176 | 0.0315 (18) | 0.0332 (18) | 0.044 (2) | 0.0045 (14) | 0.0031 (14) | 0.0022 (15) |
C17A | 0.0298 (17) | 0.0246 (15) | 0.0248 (16) | 0.0011 (12) | −0.0002 (12) | 0.0016 (12) |
C18 | 0.0300 (17) | 0.0281 (16) | 0.0288 (17) | −0.0007 (13) | −0.0033 (13) | 0.0038 (13) |
C181 | 0.045 (2) | 0.0263 (16) | 0.0253 (16) | 0.0035 (14) | −0.0015 (14) | 0.0039 (13) |
C182 | 0.049 (2) | 0.046 (2) | 0.050 (2) | −0.0103 (17) | −0.0061 (17) | 0.0218 (18) |
C183 | 0.045 (2) | 0.068 (3) | 0.058 (2) | 0.0103 (19) | −0.0006 (18) | 0.033 (2) |
C184 | 0.137 (4) | 0.039 (2) | 0.029 (2) | 0.022 (2) | 0.010 (2) | 0.0102 (17) |
N19 | 0.0377 (15) | 0.0284 (14) | 0.0229 (13) | 0.0028 (11) | −0.0011 (11) | 0.0061 (11) |
N110 | 0.0390 (15) | 0.0225 (12) | 0.0200 (13) | 0.0036 (11) | −0.0001 (10) | 0.0026 (10) |
C101 | 0.0351 (18) | 0.0217 (15) | 0.0255 (16) | 0.0010 (13) | 0.0026 (13) | 0.0021 (12) |
C102 | 0.044 (2) | 0.0317 (17) | 0.0232 (16) | 0.0025 (14) | −0.0020 (14) | 0.0008 (13) |
C103 | 0.049 (2) | 0.0291 (17) | 0.0286 (17) | 0.0061 (15) | −0.0027 (14) | 0.0051 (14) |
C104 | 0.050 (2) | 0.0234 (16) | 0.0359 (19) | 0.0046 (14) | 0.0008 (15) | 0.0011 (14) |
C105 | 0.050 (2) | 0.0268 (17) | 0.0288 (17) | 0.0009 (15) | −0.0003 (15) | −0.0032 (13) |
C106 | 0.044 (2) | 0.0282 (16) | 0.0267 (17) | 0.0023 (14) | −0.0001 (14) | 0.0024 (13) |
C10A | 0.0287 (17) | 0.0280 (16) | 0.0206 (15) | 0.0000 (13) | 0.0001 (12) | 0.0023 (12) |
N111 | 0.0308 (14) | 0.0264 (13) | 0.0220 (13) | 0.0012 (11) | 0.0019 (10) | 0.0010 (10) |
C21 | 0.0327 (18) | 0.0391 (18) | 0.0285 (17) | −0.0002 (14) | −0.0001 (13) | 0.0016 (14) |
C21A | 0.0294 (17) | 0.0313 (17) | 0.0283 (17) | 0.0030 (13) | −0.0017 (13) | −0.0023 (13) |
C21B | 0.0279 (17) | 0.0407 (18) | 0.0249 (16) | 0.0011 (14) | −0.0004 (13) | 0.0006 (14) |
C22 | 0.040 (2) | 0.043 (2) | 0.0319 (18) | −0.0025 (15) | −0.0008 (15) | 0.0068 (15) |
C23 | 0.041 (2) | 0.056 (2) | 0.0271 (18) | −0.0006 (17) | 0.0048 (15) | 0.0061 (16) |
C24 | 0.046 (2) | 0.051 (2) | 0.0333 (19) | 0.0058 (17) | 0.0082 (15) | −0.0029 (16) |
C24A | 0.0388 (19) | 0.0427 (19) | 0.0280 (17) | 0.0047 (15) | 0.0057 (14) | −0.0023 (14) |
C25 | 0.072 (3) | 0.040 (2) | 0.0335 (19) | 0.0104 (18) | 0.0106 (18) | −0.0057 (15) |
C26 | 0.064 (2) | 0.0346 (19) | 0.036 (2) | 0.0051 (17) | 0.0085 (17) | −0.0024 (15) |
C26A | 0.0408 (19) | 0.0303 (17) | 0.0287 (17) | 0.0075 (14) | 0.0053 (14) | −0.0021 (13) |
C27 | 0.0328 (18) | 0.0266 (16) | 0.0318 (17) | 0.0061 (13) | 0.0005 (13) | 0.0012 (13) |
C271 | 0.0369 (19) | 0.0263 (16) | 0.0300 (17) | 0.0079 (14) | 0.0024 (13) | −0.0017 (13) |
C272 | 0.0344 (19) | 0.0320 (17) | 0.0361 (18) | 0.0099 (14) | −0.0009 (14) | −0.0002 (14) |
C273 | 0.0358 (18) | 0.0295 (17) | 0.0344 (18) | 0.0045 (14) | −0.0016 (14) | 0.0004 (14) |
C274 | 0.043 (2) | 0.0225 (15) | 0.0269 (16) | 0.0070 (14) | 0.0011 (13) | 0.0008 (12) |
Cl27 | 0.0620 (6) | 0.0261 (4) | 0.0453 (5) | 0.0063 (4) | 0.0002 (4) | 0.0035 (4) |
C275 | 0.039 (2) | 0.0377 (19) | 0.042 (2) | 0.0146 (15) | 0.0021 (15) | 0.0038 (15) |
C276 | 0.0349 (19) | 0.0312 (17) | 0.0415 (19) | 0.0080 (14) | 0.0015 (15) | 0.0006 (14) |
C27A | 0.0312 (17) | 0.0239 (15) | 0.0257 (16) | 0.0082 (13) | 0.0005 (12) | 0.0031 (12) |
C28 | 0.0302 (17) | 0.0276 (16) | 0.0296 (17) | 0.0055 (13) | 0.0020 (13) | 0.0003 (13) |
C281 | 0.046 (2) | 0.0254 (16) | 0.0265 (16) | 0.0081 (14) | 0.0029 (14) | 0.0053 (13) |
C282 | 0.052 (2) | 0.045 (2) | 0.040 (2) | 0.0135 (17) | −0.0030 (16) | 0.0130 (16) |
C283 | 0.049 (2) | 0.0391 (19) | 0.048 (2) | 0.0065 (16) | 0.0059 (17) | 0.0184 (16) |
C284 | 0.089 (3) | 0.0350 (19) | 0.0293 (19) | 0.0168 (19) | 0.0062 (18) | 0.0111 (15) |
N29 | 0.0428 (16) | 0.0271 (14) | 0.0240 (13) | 0.0073 (12) | −0.0004 (11) | 0.0033 (11) |
N210 | 0.0406 (15) | 0.0238 (13) | 0.0216 (13) | 0.0051 (11) | 0.0004 (11) | 0.0026 (10) |
C201 | 0.0362 (18) | 0.0219 (15) | 0.0309 (17) | 0.0039 (13) | 0.0021 (13) | 0.0045 (13) |
C202 | 0.049 (2) | 0.0283 (16) | 0.0247 (16) | 0.0074 (14) | −0.0033 (14) | 0.0016 (13) |
C203 | 0.059 (2) | 0.0308 (18) | 0.0347 (19) | 0.0139 (16) | −0.0038 (16) | 0.0069 (15) |
C204 | 0.061 (2) | 0.0230 (16) | 0.041 (2) | 0.0110 (16) | −0.0057 (17) | 0.0008 (15) |
C205 | 0.066 (2) | 0.0278 (17) | 0.0360 (19) | 0.0041 (16) | −0.0169 (17) | −0.0043 (14) |
C206 | 0.054 (2) | 0.0293 (17) | 0.0327 (18) | 0.0069 (15) | −0.0058 (15) | 0.0021 (14) |
C20A | 0.0327 (17) | 0.0269 (16) | 0.0256 (16) | 0.0058 (13) | 0.0013 (13) | −0.0019 (13) |
N211 | 0.0349 (15) | 0.0286 (13) | 0.0224 (13) | 0.0024 (11) | 0.0008 (11) | 0.0001 (11) |
C31 | 0.046 (2) | 0.0324 (18) | 0.0330 (18) | 0.0044 (15) | 0.0050 (15) | −0.0002 (14) |
C31A | 0.0297 (17) | 0.0290 (17) | 0.0353 (18) | 0.0033 (13) | 0.0068 (14) | −0.0026 (14) |
C31B | 0.0324 (18) | 0.0304 (17) | 0.0327 (17) | 0.0066 (14) | 0.0081 (13) | 0.0028 (13) |
C32 | 0.046 (2) | 0.0347 (18) | 0.045 (2) | 0.0059 (16) | 0.0095 (16) | 0.0108 (16) |
C33 | 0.040 (2) | 0.047 (2) | 0.0363 (19) | 0.0102 (16) | 0.0088 (15) | 0.0066 (16) |
C34 | 0.041 (2) | 0.046 (2) | 0.0331 (19) | 0.0096 (16) | 0.0044 (15) | −0.0024 (15) |
C34A | 0.0397 (19) | 0.0331 (17) | 0.0352 (19) | 0.0059 (15) | 0.0084 (14) | −0.0014 (14) |
C35 | 0.068 (3) | 0.038 (2) | 0.038 (2) | 0.0046 (18) | 0.0053 (18) | −0.0026 (16) |
C36 | 0.061 (2) | 0.0306 (18) | 0.038 (2) | 0.0059 (16) | 0.0114 (17) | −0.0009 (15) |
C36A | 0.0372 (19) | 0.0301 (17) | 0.0353 (18) | 0.0065 (14) | 0.0066 (14) | −0.0015 (14) |
C37 | 0.0294 (17) | 0.0234 (15) | 0.0379 (18) | 0.0043 (13) | 0.0041 (13) | 0.0024 (13) |
C371 | 0.044 (2) | 0.0283 (16) | 0.0322 (18) | 0.0118 (15) | 0.0021 (14) | 0.0008 (13) |
C372 | 0.045 (2) | 0.040 (2) | 0.064 (2) | 0.0181 (17) | 0.0075 (18) | 0.0002 (18) |
C373 | 0.065 (3) | 0.044 (2) | 0.055 (2) | 0.032 (2) | −0.002 (2) | −0.0046 (18) |
C374 | 0.074 (3) | 0.0262 (17) | 0.0251 (17) | 0.0160 (18) | −0.0014 (16) | −0.0013 (13) |
Cl37 | 0.1333 (10) | 0.0290 (5) | 0.0401 (5) | 0.0305 (5) | −0.0054 (5) | 0.0012 (4) |
C375 | 0.058 (2) | 0.0284 (17) | 0.0289 (18) | 0.0047 (16) | 0.0004 (15) | 0.0006 (14) |
C376 | 0.044 (2) | 0.0263 (16) | 0.0261 (16) | 0.0073 (14) | 0.0004 (14) | −0.0004 (13) |
C37A | 0.0311 (17) | 0.0262 (16) | 0.0331 (17) | 0.0060 (13) | 0.0003 (13) | 0.0052 (13) |
C38 | 0.0303 (17) | 0.0256 (16) | 0.0377 (18) | 0.0057 (13) | −0.0008 (13) | 0.0028 (13) |
C381 | 0.045 (2) | 0.0248 (16) | 0.0353 (18) | 0.0053 (14) | −0.0008 (15) | 0.0042 (13) |
C382 | 0.047 (2) | 0.0344 (18) | 0.0400 (19) | 0.0014 (16) | 0.0037 (16) | 0.0040 (15) |
C383 | 0.051 (2) | 0.046 (2) | 0.065 (3) | 0.0155 (18) | 0.0032 (19) | 0.0239 (19) |
C384 | 0.080 (3) | 0.040 (2) | 0.037 (2) | −0.0028 (19) | −0.0195 (19) | 0.0100 (16) |
N39 | 0.0403 (16) | 0.0272 (14) | 0.0313 (14) | 0.0060 (12) | −0.0024 (12) | 0.0054 (11) |
N310 | 0.0380 (15) | 0.0267 (13) | 0.0298 (14) | 0.0055 (11) | −0.0029 (11) | 0.0024 (11) |
C301 | 0.0373 (18) | 0.0207 (15) | 0.0338 (17) | 0.0061 (13) | 0.0039 (14) | 0.0011 (13) |
C302 | 0.056 (2) | 0.0327 (18) | 0.0332 (18) | 0.0137 (16) | −0.0087 (16) | −0.0029 (14) |
C303 | 0.074 (3) | 0.0303 (18) | 0.042 (2) | 0.0199 (18) | −0.0026 (18) | 0.0044 (16) |
C304 | 0.062 (2) | 0.0232 (16) | 0.044 (2) | 0.0108 (16) | 0.0021 (17) | −0.0030 (15) |
C305 | 0.045 (2) | 0.0296 (17) | 0.0356 (18) | 0.0026 (15) | 0.0007 (15) | −0.0049 (14) |
C306 | 0.0343 (18) | 0.0329 (17) | 0.0302 (17) | 0.0041 (14) | 0.0023 (13) | 0.0050 (14) |
C30A | 0.0334 (18) | 0.0273 (16) | 0.0307 (17) | 0.0039 (13) | 0.0022 (13) | −0.0038 (13) |
N311 | 0.0347 (15) | 0.0271 (13) | 0.0300 (14) | 0.0045 (11) | 0.0038 (11) | 0.0024 (11) |
Geometric parameters (Å, º) top
C11—C12 | 1.384 (4) | C276—H276 | 0.95 |
C11—C11B | 1.395 (4) | C27A—C20A | 1.413 (4) |
C11—H11 | 0.95 | C27A—C28 | 1.447 (4) |
C11A—N111 | 1.335 (3) | C28—N29 | 1.326 (4) |
C11A—C16A | 1.421 (4) | C28—C281 | 1.519 (4) |
C11A—C11B | 1.475 (4) | C281—C283 | 1.522 (4) |
C11B—C14A | 1.389 (4) | C281—C284 | 1.528 (4) |
C12—C13 | 1.374 (4) | C281—C282 | 1.530 (4) |
C12—H12 | 0.95 | C282—H28A | 0.98 |
C13—C14 | 1.378 (4) | C282—H28B | 0.98 |
C13—H13 | 0.95 | C282—H28C | 0.98 |
C14—C14A | 1.389 (4) | C283—H28D | 0.98 |
C14—H14 | 0.95 | C283—H28E | 0.98 |
C14A—C15 | 1.495 (4) | C283—H28F | 0.98 |
C15—C16 | 1.468 (5) | C284—H28G | 0.98 |
C15—H15A | 0.99 | C284—H28H | 0.98 |
C15—H15B | 0.99 | C284—H28I | 0.98 |
C16—C16A | 1.496 (4) | N29—N210 | 1.372 (3) |
C16—H16A | 0.99 | N210—C20A | 1.365 (3) |
C16—H16B | 0.99 | N210—C201 | 1.418 (3) |
C16A—C17 | 1.396 (4) | C201—C202 | 1.383 (4) |
C17—C17A | 1.414 (4) | C201—C206 | 1.387 (4) |
C17—C171 | 1.494 (4) | C202—C203 | 1.391 (4) |
C171—C172 | 1.380 (4) | C202—H202 | 0.95 |
C171—C176 | 1.380 (4) | C203—C204 | 1.378 (4) |
C172—C173 | 1.392 (4) | C203—H203 | 0.95 |
C172—H172 | 0.95 | C204—C205 | 1.372 (4) |
C173—C174 | 1.363 (4) | C204—H204 | 0.95 |
C173—H173 | 0.95 | C205—C206 | 1.385 (4) |
C174—C175 | 1.375 (4) | C205—H205 | 0.95 |
C174—Cl17 | 1.735 (3) | C206—H206 | 0.95 |
C175—C176 | 1.389 (4) | C20A—N211 | 1.329 (4) |
C175—H175 | 0.95 | C31—C32 | 1.383 (4) |
C176—H176 | 0.95 | C31—C31B | 1.392 (4) |
C17A—C10A | 1.418 (4) | C31—H31 | 0.95 |
C17A—C18 | 1.451 (4) | C31A—N311 | 1.338 (4) |
C18—N19 | 1.319 (4) | C31A—C36A | 1.412 (4) |
C18—C181 | 1.522 (4) | C31A—C31B | 1.478 (4) |
C181—C183 | 1.517 (5) | C31B—C34A | 1.405 (4) |
C181—C184 | 1.523 (4) | C32—C33 | 1.385 (5) |
C181—C182 | 1.527 (4) | C32—H32 | 0.95 |
C182—H18A | 0.98 | C33—C34 | 1.380 (4) |
C182—H18B | 0.98 | C33—H33 | 0.95 |
C182—H18C | 0.98 | C34—C34A | 1.388 (4) |
C183—H18D | 0.98 | C34—H34 | 0.95 |
C183—H18E | 0.98 | C34A—C35 | 1.487 (4) |
C183—H18F | 0.98 | C35—C36 | 1.469 (5) |
C184—H18G | 0.98 | C35—H35A | 0.99 |
C184—H18H | 0.98 | C35—H35B | 0.99 |
C184—H18I | 0.98 | C36—C36A | 1.494 (4) |
N19—N110 | 1.369 (3) | C36—H36A | 0.99 |
N110—C10A | 1.368 (3) | C36—H36B | 0.99 |
N110—C101 | 1.416 (3) | C36A—C37 | 1.397 (4) |
C101—C106 | 1.385 (4) | C37—C37A | 1.417 (4) |
C101—C102 | 1.385 (4) | C37—C371 | 1.493 (4) |
C102—C103 | 1.386 (4) | C371—C376 | 1.384 (4) |
C102—H102 | 0.95 | C371—C372 | 1.388 (4) |
C103—C104 | 1.373 (4) | C372—C373 | 1.388 (5) |
C103—H103 | 0.95 | C372—H372 | 0.95 |
C104—C105 | 1.382 (4) | C373—C374 | 1.381 (5) |
C104—H104 | 0.95 | C373—H373 | 0.95 |
C105—C106 | 1.383 (4) | C374—C375 | 1.364 (5) |
C105—H105 | 0.95 | C374—Cl37 | 1.736 (3) |
C106—H106 | 0.95 | C375—C376 | 1.386 (4) |
C10A—N111 | 1.329 (3) | C375—H375 | 0.95 |
C21—C22 | 1.381 (4) | C376—H376 | 0.95 |
C21—C21B | 1.391 (4) | C37A—C30A | 1.407 (4) |
C21—H21 | 0.95 | C37A—C38 | 1.453 (4) |
C21A—N211 | 1.333 (4) | C38—N39 | 1.328 (4) |
C21A—C26A | 1.423 (4) | C38—C381 | 1.529 (4) |
C21A—C21B | 1.480 (4) | C381—C382 | 1.520 (4) |
C21B—C24A | 1.399 (4) | C381—C384 | 1.523 (4) |
C22—C23 | 1.390 (4) | C381—C383 | 1.536 (4) |
C22—H22 | 0.95 | C382—H38A | 0.98 |
C23—C24 | 1.378 (4) | C382—H38B | 0.98 |
C23—H23 | 0.95 | C382—H38C | 0.98 |
C24—C24A | 1.396 (4) | C383—H38D | 0.98 |
C24—H24 | 0.95 | C383—H38E | 0.98 |
C24A—C25 | 1.478 (4) | C383—H38F | 0.98 |
C25—C26 | 1.477 (5) | C384—H38G | 0.98 |
C25—H25A | 0.99 | C384—H38H | 0.98 |
C25—H25B | 0.99 | C384—H38I | 0.98 |
C26—C26A | 1.496 (4) | N39—N310 | 1.369 (3) |
C26—H26A | 0.99 | N310—C30A | 1.370 (4) |
C26—H26B | 0.99 | N310—C301 | 1.418 (3) |
C26A—C27 | 1.399 (4) | C301—C302 | 1.385 (4) |
C27—C27A | 1.415 (4) | C301—C306 | 1.385 (4) |
C27—C271 | 1.491 (4) | C302—C303 | 1.385 (4) |
C271—C276 | 1.383 (4) | C302—H302 | 0.95 |
C271—C272 | 1.392 (4) | C303—C304 | 1.381 (5) |
C272—C273 | 1.389 (4) | C303—H303 | 0.95 |
C272—H272 | 0.95 | C304—C305 | 1.376 (4) |
C273—C274 | 1.374 (4) | C304—H304 | 0.95 |
C273—H273 | 0.95 | C305—C306 | 1.379 (4) |
C274—C275 | 1.381 (4) | C305—H305 | 0.95 |
C274—Cl27 | 1.741 (3) | C306—H306 | 0.95 |
C275—C276 | 1.392 (4) | C30A—N311 | 1.332 (4) |
C275—H275 | 0.95 | | |
| | | |
C12—C11—C11B | 120.1 (3) | C20A—C27A—C27 | 115.3 (3) |
C12—C11—H11 | 120.0 | C20A—C27A—C28 | 104.1 (2) |
C11B—C11—H11 | 120.0 | C27—C27A—C28 | 140.5 (3) |
N111—C11A—C16A | 123.2 (3) | N29—C28—C27A | 110.2 (2) |
N111—C11A—C11B | 116.5 (2) | N29—C28—C281 | 116.7 (3) |
C16A—C11A—C11B | 120.3 (3) | C27A—C28—C281 | 133.1 (3) |
C14A—C11B—C11 | 119.4 (3) | C28—C281—C283 | 111.3 (2) |
C14A—C11B—C11A | 120.0 (3) | C28—C281—C284 | 109.4 (2) |
C11—C11B—C11A | 120.6 (3) | C283—C281—C284 | 107.7 (3) |
C13—C12—C11 | 120.4 (3) | C28—C281—C282 | 110.1 (3) |
C13—C12—H12 | 119.8 | C283—C281—C282 | 110.6 (3) |
C11—C12—H12 | 119.8 | C284—C281—C282 | 107.6 (3) |
C12—C13—C14 | 119.8 (3) | C281—C282—H28A | 109.5 |
C12—C13—H13 | 120.1 | C281—C282—H28B | 109.5 |
C14—C13—H13 | 120.1 | H28A—C282—H28B | 109.5 |
C13—C14—C14A | 120.7 (3) | C281—C282—H28C | 109.5 |
C13—C14—H14 | 119.7 | H28A—C282—H28C | 109.5 |
C14A—C14—H14 | 119.7 | H28B—C282—H28C | 109.5 |
C14—C14A—C11B | 119.6 (3) | C281—C283—H28D | 109.5 |
C14—C14A—C15 | 121.7 (3) | C281—C283—H28E | 109.5 |
C11B—C14A—C15 | 118.6 (3) | H28D—C283—H28E | 109.5 |
C16—C15—C14A | 113.6 (3) | C281—C283—H28F | 109.5 |
C16—C15—H15A | 108.8 | H28D—C283—H28F | 109.5 |
C14A—C15—H15A | 108.8 | H28E—C283—H28F | 109.5 |
C16—C15—H15B | 108.8 | C281—C284—H28G | 109.5 |
C14A—C15—H15B | 108.8 | C281—C284—H28H | 109.5 |
H15A—C15—H15B | 107.7 | H28G—C284—H28H | 109.5 |
C15—C16—C16A | 114.2 (3) | C281—C284—H28I | 109.5 |
C15—C16—H16A | 108.7 | H28G—C284—H28I | 109.5 |
C16A—C16—H16A | 108.7 | H28H—C284—H28I | 109.5 |
C15—C16—H16B | 108.7 | C28—N29—N210 | 107.6 (2) |
C16A—C16—H16B | 108.7 | C20A—N210—N29 | 110.6 (2) |
H16A—C16—H16B | 107.6 | C20A—N210—C201 | 130.1 (2) |
C17—C16A—C11A | 120.3 (3) | N29—N210—C201 | 119.1 (2) |
C17—C16A—C16 | 122.7 (3) | C202—C201—C206 | 120.3 (3) |
C11A—C16A—C16 | 116.9 (3) | C202—C201—N210 | 120.4 (3) |
C16A—C17—C17A | 117.6 (3) | C206—C201—N210 | 119.2 (3) |
C16A—C17—C171 | 117.8 (3) | C201—C202—C203 | 119.3 (3) |
C17A—C17—C171 | 124.6 (3) | C201—C202—H202 | 120.4 |
C172—C171—C176 | 118.3 (3) | C203—C202—H202 | 120.4 |
C172—C171—C17 | 120.0 (3) | C204—C203—C202 | 120.5 (3) |
C176—C171—C17 | 121.6 (3) | C204—C203—H203 | 119.8 |
C171—C172—C173 | 120.8 (3) | C202—C203—H203 | 119.8 |
C171—C172—H172 | 119.6 | C205—C204—C203 | 119.8 (3) |
C173—C172—H172 | 119.6 | C205—C204—H204 | 120.1 |
C174—C173—C172 | 119.6 (3) | C203—C204—H204 | 120.1 |
C174—C173—H173 | 120.2 | C204—C205—C206 | 120.6 (3) |
C172—C173—H173 | 120.2 | C204—C205—H205 | 119.7 |
C173—C174—C175 | 120.9 (3) | C206—C205—H205 | 119.7 |
C173—C174—Cl17 | 119.5 (3) | C205—C206—C201 | 119.5 (3) |
C175—C174—Cl17 | 119.6 (2) | C205—C206—H206 | 120.3 |
C174—C175—C176 | 119.0 (3) | C201—C206—H206 | 120.3 |
C174—C175—H175 | 120.5 | N211—C20A—N210 | 123.9 (3) |
C176—C175—H175 | 120.5 | N211—C20A—C27A | 128.6 (3) |
C171—C176—C175 | 121.3 (3) | N210—C20A—C27A | 107.5 (2) |
C171—C176—H176 | 119.3 | C20A—N211—C21A | 114.7 (2) |
C175—C176—H176 | 119.3 | C32—C31—C31B | 120.6 (3) |
C17—C17A—C10A | 115.8 (2) | C32—C31—H31 | 119.7 |
C17—C17A—C18 | 140.6 (3) | C31B—C31—H31 | 119.7 |
C10A—C17A—C18 | 103.7 (2) | N311—C31A—C36A | 123.7 (3) |
N19—C18—C17A | 110.1 (2) | N311—C31A—C31B | 116.2 (3) |
N19—C18—C181 | 116.5 (3) | C36A—C31A—C31B | 120.1 (3) |
C17A—C18—C181 | 133.4 (3) | C31—C31B—C34A | 119.2 (3) |
C183—C181—C18 | 112.3 (3) | C31—C31B—C31A | 121.1 (3) |
C183—C181—C184 | 107.7 (3) | C34A—C31B—C31A | 119.7 (3) |
C18—C181—C184 | 109.8 (2) | C31—C32—C33 | 120.1 (3) |
C183—C181—C182 | 110.2 (3) | C31—C32—H32 | 120.0 |
C18—C181—C182 | 109.3 (2) | C33—C32—H32 | 120.0 |
C184—C181—C182 | 107.3 (3) | C34—C33—C32 | 119.8 (3) |
C181—C182—H18A | 109.5 | C34—C33—H33 | 120.1 |
C181—C182—H18B | 109.5 | C32—C33—H33 | 120.1 |
H18A—C182—H18B | 109.5 | C33—C34—C34A | 120.9 (3) |
C181—C182—H18C | 109.5 | C33—C34—H34 | 119.5 |
H18A—C182—H18C | 109.5 | C34A—C34—H34 | 119.5 |
H18B—C182—H18C | 109.5 | C34—C34A—C31B | 119.3 (3) |
C181—C183—H18D | 109.5 | C34—C34A—C35 | 122.3 (3) |
C181—C183—H18E | 109.5 | C31B—C34A—C35 | 118.3 (3) |
H18D—C183—H18E | 109.5 | C36—C35—C34A | 114.9 (3) |
C181—C183—H18F | 109.5 | C36—C35—H35A | 108.6 |
H18D—C183—H18F | 109.5 | C34A—C35—H35A | 108.6 |
H18E—C183—H18F | 109.5 | C36—C35—H35B | 108.6 |
C181—C184—H18G | 109.5 | C34A—C35—H35B | 108.6 |
C181—C184—H18H | 109.5 | H35A—C35—H35B | 107.5 |
H18G—C184—H18H | 109.5 | C35—C36—C36A | 113.7 (3) |
C181—C184—H18I | 109.5 | C35—C36—H36A | 108.8 |
H18G—C184—H18I | 109.5 | C36A—C36—H36A | 108.8 |
H18H—C184—H18I | 109.5 | C35—C36—H36B | 108.8 |
C18—N19—N110 | 108.3 (2) | C36A—C36—H36B | 108.8 |
C10A—N110—N19 | 110.1 (2) | H36A—C36—H36B | 107.7 |
C10A—N110—C101 | 130.8 (2) | C37—C36A—C31A | 120.0 (3) |
N19—N110—C101 | 119.0 (2) | C37—C36A—C36 | 121.8 (3) |
C106—C101—C102 | 120.1 (3) | C31A—C36A—C36 | 118.2 (3) |
C106—C101—N110 | 118.9 (2) | C36A—C37—C37A | 117.8 (3) |
C102—C101—N110 | 120.9 (3) | C36A—C37—C371 | 118.8 (3) |
C101—C102—C103 | 119.2 (3) | C37A—C37—C371 | 123.4 (3) |
C101—C102—H102 | 120.4 | C376—C371—C372 | 118.3 (3) |
C103—C102—H102 | 120.4 | C376—C371—C37 | 121.2 (3) |
C104—C103—C102 | 121.0 (3) | C372—C371—C37 | 120.5 (3) |
C104—C103—H103 | 119.5 | C371—C372—C373 | 120.8 (3) |
C102—C103—H103 | 119.5 | C371—C372—H372 | 119.6 |
C103—C104—C105 | 119.4 (3) | C373—C372—H372 | 119.6 |
C103—C104—H104 | 120.3 | C374—C373—C372 | 119.2 (3) |
C105—C104—H104 | 120.3 | C374—C373—H373 | 120.4 |
C104—C105—C106 | 120.4 (3) | C372—C373—H373 | 120.4 |
C104—C105—H105 | 119.8 | C375—C374—C373 | 121.1 (3) |
C106—C105—H105 | 119.8 | C375—C374—Cl37 | 119.2 (3) |
C105—C106—C101 | 119.8 (3) | C373—C374—Cl37 | 119.7 (3) |
C105—C106—H106 | 120.1 | C374—C375—C376 | 119.3 (3) |
C101—C106—H106 | 120.1 | C374—C375—H375 | 120.4 |
N111—C10A—N110 | 124.3 (2) | C376—C375—H375 | 120.4 |
N111—C10A—C17A | 127.9 (3) | C371—C376—C375 | 121.3 (3) |
N110—C10A—C17A | 107.7 (2) | C371—C376—H376 | 119.3 |
C10A—N111—C11A | 115.1 (2) | C375—C376—H376 | 119.3 |
C22—C21—C21B | 120.7 (3) | C30A—C37A—C37 | 115.6 (3) |
C22—C21—H21 | 119.6 | C30A—C37A—C38 | 104.1 (2) |
C21B—C21—H21 | 119.6 | C37—C37A—C38 | 140.3 (3) |
N211—C21A—C26A | 123.5 (3) | N39—C38—C37A | 109.9 (3) |
N211—C21A—C21B | 116.2 (3) | N39—C38—C381 | 116.3 (3) |
C26A—C21A—C21B | 120.3 (3) | C37A—C38—C381 | 133.8 (3) |
C21—C21B—C24A | 120.1 (3) | C382—C381—C384 | 108.1 (3) |
C21—C21B—C21A | 120.6 (3) | C382—C381—C38 | 110.2 (2) |
C24A—C21B—C21A | 119.2 (3) | C384—C381—C38 | 109.3 (2) |
C21—C22—C23 | 119.6 (3) | C382—C381—C383 | 109.7 (3) |
C21—C22—H22 | 120.2 | C384—C381—C383 | 108.7 (3) |
C23—C22—H22 | 120.2 | C38—C381—C383 | 110.9 (3) |
C24—C23—C22 | 119.8 (3) | C381—C382—H38A | 109.5 |
C24—C23—H23 | 120.1 | C381—C382—H38B | 109.5 |
C22—C23—H23 | 120.1 | H38A—C382—H38B | 109.5 |
C23—C24—C24A | 121.6 (3) | C381—C382—H38C | 109.5 |
C23—C24—H24 | 119.2 | H38A—C382—H38C | 109.5 |
C24A—C24—H24 | 119.2 | H38B—C382—H38C | 109.5 |
C24—C24A—C21B | 118.2 (3) | C381—C383—H38D | 109.5 |
C24—C24A—C25 | 122.6 (3) | C381—C383—H38E | 109.5 |
C21B—C24A—C25 | 119.2 (3) | H38D—C383—H38E | 109.5 |
C26—C25—C24A | 114.0 (3) | C381—C383—H38F | 109.5 |
C26—C25—H25A | 108.7 | H38D—C383—H38F | 109.5 |
C24A—C25—H25A | 108.7 | H38E—C383—H38F | 109.5 |
C26—C25—H25B | 108.7 | C381—C384—H38G | 109.5 |
C24A—C25—H25B | 108.7 | C381—C384—H38H | 109.5 |
H25A—C25—H25B | 107.6 | H38G—C384—H38H | 109.5 |
C25—C26—C26A | 113.6 (3) | C381—C384—H38I | 109.5 |
C25—C26—H26A | 108.9 | H38G—C384—H38I | 109.5 |
C26A—C26—H26A | 108.9 | H38H—C384—H38I | 109.5 |
C25—C26—H26B | 108.9 | C38—N39—N310 | 107.8 (2) |
C26A—C26—H26B | 108.9 | N39—N310—C30A | 110.6 (2) |
H26A—C26—H26B | 107.7 | N39—N310—C301 | 118.7 (2) |
C27—C26A—C21A | 120.0 (3) | C30A—N310—C301 | 130.7 (2) |
C27—C26A—C26 | 122.6 (3) | C302—C301—C306 | 120.3 (3) |
C21A—C26A—C26 | 117.3 (3) | C302—C301—N310 | 120.6 (3) |
C26A—C27—C27A | 117.8 (3) | C306—C301—N310 | 119.1 (3) |
C26A—C27—C271 | 118.0 (3) | C301—C302—C303 | 119.1 (3) |
C27A—C27—C271 | 124.0 (3) | C301—C302—H302 | 120.5 |
C276—C271—C272 | 118.2 (3) | C303—C302—H302 | 120.5 |
C276—C271—C27 | 122.8 (3) | C304—C303—C302 | 120.9 (3) |
C272—C271—C27 | 118.9 (3) | C304—C303—H303 | 119.6 |
C273—C272—C271 | 121.2 (3) | C302—C303—H303 | 119.6 |
C273—C272—H272 | 119.4 | C305—C304—C303 | 119.4 (3) |
C271—C272—H272 | 119.4 | C305—C304—H304 | 120.3 |
C274—C273—C272 | 119.2 (3) | C303—C304—H304 | 120.3 |
C274—C273—H273 | 120.4 | C304—C305—C306 | 120.6 (3) |
C272—C273—H273 | 120.4 | C304—C305—H305 | 119.7 |
C273—C274—C275 | 121.2 (3) | C306—C305—H305 | 119.7 |
C273—C274—Cl27 | 119.1 (2) | C305—C306—C301 | 119.7 (3) |
C275—C274—Cl27 | 119.7 (2) | C305—C306—H306 | 120.1 |
C274—C275—C276 | 118.9 (3) | C301—C306—H306 | 120.1 |
C274—C275—H275 | 120.6 | N311—C30A—N310 | 124.0 (3) |
C276—C275—H275 | 120.6 | N311—C30A—C37A | 128.4 (3) |
C271—C276—C275 | 121.4 (3) | N310—C30A—C37A | 107.6 (3) |
C271—C276—H276 | 119.3 | C30A—N311—C31A | 114.5 (2) |
C275—C276—H276 | 119.3 | | |
| | | |
C12—C11—C11B—C14A | 0.9 (5) | C26A—C27—C27A—C20A | 4.7 (4) |
C12—C11—C11B—C11A | 179.7 (3) | C271—C27—C27A—C20A | −170.6 (3) |
N111—C11A—C11B—C14A | 166.2 (3) | C26A—C27—C27A—C28 | −179.7 (3) |
C16A—C11A—C11B—C14A | −12.5 (4) | C271—C27—C27A—C28 | 5.1 (6) |
N111—C11A—C11B—C11 | −12.5 (4) | C20A—C27A—C28—N29 | 1.1 (3) |
C16A—C11A—C11B—C11 | 168.8 (3) | C27—C27A—C28—N29 | −174.9 (4) |
C11B—C11—C12—C13 | −0.1 (5) | C20A—C27A—C28—C281 | −176.6 (3) |
C11—C12—C13—C14 | −0.5 (5) | C27—C27A—C28—C281 | 7.4 (6) |
C12—C13—C14—C14A | 0.3 (5) | N29—C28—C281—C283 | 122.4 (3) |
C13—C14—C14A—C11B | 0.5 (5) | C27A—C28—C281—C283 | −60.0 (4) |
C13—C14—C14A—C15 | −176.6 (3) | N29—C28—C281—C284 | 3.5 (4) |
C11—C11B—C14A—C14 | −1.2 (5) | C27A—C28—C281—C284 | −178.9 (3) |
C11A—C11B—C14A—C14 | −179.9 (3) | N29—C28—C281—C282 | −114.6 (3) |
C11—C11B—C14A—C15 | 176.1 (3) | C27A—C28—C281—C282 | 63.0 (4) |
C11A—C11B—C14A—C15 | −2.7 (5) | C27A—C28—N29—N210 | −0.2 (3) |
C14—C14A—C15—C16 | −150.1 (3) | C281—C28—N29—N210 | 177.9 (2) |
C11B—C14A—C15—C16 | 32.7 (5) | C28—N29—N210—C20A | −0.8 (3) |
C14A—C15—C16—C16A | −47.7 (4) | C28—N29—N210—C201 | 175.6 (2) |
N111—C11A—C16A—C17 | −0.3 (4) | C20A—N210—C201—C202 | 26.7 (5) |
C11B—C11A—C16A—C17 | 178.3 (3) | N29—N210—C201—C202 | −149.0 (3) |
N111—C11A—C16A—C16 | 177.9 (3) | C20A—N210—C201—C206 | −155.6 (3) |
C11B—C11A—C16A—C16 | −3.5 (4) | N29—N210—C201—C206 | 28.7 (4) |
C15—C16—C16A—C17 | −148.2 (3) | C206—C201—C202—C203 | 0.3 (5) |
C15—C16—C16A—C11A | 33.6 (4) | N210—C201—C202—C203 | 178.0 (3) |
C11A—C16A—C17—C17A | −0.6 (4) | C201—C202—C203—C204 | −1.4 (5) |
C16—C16A—C17—C17A | −178.7 (3) | C202—C203—C204—C205 | 1.1 (5) |
C11A—C16A—C17—C171 | −179.5 (3) | C203—C204—C205—C206 | 0.3 (6) |
C16—C16A—C17—C171 | 2.3 (4) | C204—C205—C206—C201 | −1.4 (5) |
C16A—C17—C171—C172 | −87.8 (4) | C202—C201—C206—C205 | 1.1 (5) |
C17A—C17—C171—C172 | 93.3 (4) | N210—C201—C206—C205 | −176.7 (3) |
C16A—C17—C171—C176 | 89.1 (4) | N29—N210—C20A—N211 | −178.5 (3) |
C17A—C17—C171—C176 | −89.8 (4) | C201—N210—C20A—N211 | 5.6 (5) |
C176—C171—C172—C173 | 1.7 (5) | N29—N210—C20A—C27A | 1.5 (3) |
C17—C171—C172—C173 | 178.8 (3) | C201—N210—C20A—C27A | −174.4 (3) |
C171—C172—C173—C174 | −0.1 (5) | C27—C27A—C20A—N211 | −4.3 (5) |
C172—C173—C174—C175 | −2.0 (5) | C28—C27A—C20A—N211 | 178.5 (3) |
C172—C173—C174—Cl17 | 178.6 (3) | C27—C27A—C20A—N210 | 175.6 (3) |
C173—C174—C175—C176 | 2.4 (5) | C28—C27A—C20A—N210 | −1.6 (3) |
Cl17—C174—C175—C176 | −178.1 (2) | N210—C20A—N211—C21A | −179.5 (3) |
C172—C171—C176—C175 | −1.3 (5) | C27A—C20A—N211—C21A | 0.5 (4) |
C17—C171—C176—C175 | −178.3 (3) | C26A—C21A—N211—C20A | 2.9 (4) |
C174—C175—C176—C171 | −0.8 (5) | C21B—C21A—N211—C20A | −179.3 (2) |
C16A—C17—C17A—C10A | 0.8 (4) | C32—C31—C31B—C34A | 1.3 (5) |
C171—C17—C17A—C10A | 179.6 (3) | C32—C31—C31B—C31A | 180.0 (3) |
C16A—C17—C17A—C18 | −178.7 (3) | N311—C31A—C31B—C31 | −12.0 (4) |
C171—C17—C17A—C18 | 0.2 (6) | C36A—C31A—C31B—C31 | 168.0 (3) |
C17—C17A—C18—N19 | 178.9 (3) | N311—C31A—C31B—C34A | 166.7 (3) |
C10A—C17A—C18—N19 | −0.5 (3) | C36A—C31A—C31B—C34A | −13.3 (4) |
C17—C17A—C18—C181 | 0.7 (6) | C31B—C31—C32—C33 | −0.4 (5) |
C10A—C17A—C18—C181 | −178.8 (3) | C31—C32—C33—C34 | −0.2 (5) |
N19—C18—C181—C183 | 121.7 (3) | C32—C33—C34—C34A | 0.0 (5) |
C17A—C18—C181—C183 | −60.1 (4) | C33—C34—C34A—C31B | 0.9 (5) |
N19—C18—C181—C184 | 1.9 (4) | C33—C34—C34A—C35 | −177.5 (3) |
C17A—C18—C181—C184 | −180.0 (3) | C31—C31B—C34A—C34 | −1.5 (5) |
N19—C18—C181—C182 | −115.6 (3) | C31A—C31B—C34A—C34 | 179.8 (3) |
C17A—C18—C181—C182 | 62.6 (4) | C31—C31B—C34A—C35 | 176.9 (3) |
C17A—C18—N19—N110 | 0.3 (3) | C31A—C31B—C34A—C35 | −1.8 (4) |
C181—C18—N19—N110 | 178.8 (2) | C34—C34A—C35—C36 | −150.1 (3) |
C18—N19—N110—C10A | 0.1 (3) | C31B—C34A—C35—C36 | 31.5 (4) |
C18—N19—N110—C101 | −177.8 (2) | C34A—C35—C36—C36A | −45.7 (4) |
C10A—N110—C101—C106 | 161.0 (3) | N311—C31A—C36A—C37 | −0.7 (5) |
N19—N110—C101—C106 | −21.6 (4) | C31B—C31A—C36A—C37 | 179.2 (3) |
C10A—N110—C101—C102 | −21.6 (5) | N311—C31A—C36A—C36 | 177.8 (3) |
N19—N110—C101—C102 | 155.9 (3) | C31B—C31A—C36A—C36 | −2.2 (4) |
C106—C101—C102—C103 | −0.5 (5) | C35—C36—C36A—C37 | −150.0 (3) |
N110—C101—C102—C103 | −177.9 (3) | C35—C36—C36A—C31A | 31.5 (4) |
C101—C102—C103—C104 | 1.4 (5) | C31A—C36A—C37—C37A | −1.3 (4) |
C102—C103—C104—C105 | −1.5 (5) | C36—C36A—C37—C37A | −179.8 (3) |
C103—C104—C105—C106 | 0.6 (5) | C31A—C36A—C37—C371 | 178.0 (3) |
C104—C105—C106—C101 | 0.3 (5) | C36—C36A—C37—C371 | −0.5 (4) |
C102—C101—C106—C105 | −0.4 (5) | C36A—C37—C371—C376 | 94.4 (4) |
N110—C101—C106—C105 | 177.1 (3) | C37A—C37—C371—C376 | −86.3 (4) |
N19—N110—C10A—N111 | −179.4 (3) | C36A—C37—C371—C372 | −82.7 (4) |
C101—N110—C10A—N111 | −1.8 (5) | C37A—C37—C371—C372 | 96.6 (4) |
N19—N110—C10A—C17A | −0.4 (3) | C376—C371—C372—C373 | 2.1 (5) |
C101—N110—C10A—C17A | 177.2 (3) | C37—C371—C372—C373 | 179.2 (3) |
C17—C17A—C10A—N111 | −0.1 (4) | C371—C372—C373—C374 | −1.1 (5) |
C18—C17A—C10A—N111 | 179.5 (3) | C372—C373—C374—C375 | −0.7 (5) |
C17—C17A—C10A—N110 | −179.0 (2) | C372—C373—C374—Cl37 | −179.8 (3) |
C18—C17A—C10A—N110 | 0.6 (3) | C373—C374—C375—C376 | 1.3 (5) |
N110—C10A—N111—C11A | 178.0 (3) | Cl37—C374—C375—C376 | −179.6 (2) |
C17A—C10A—N111—C11A | −0.8 (4) | C372—C371—C376—C375 | −1.4 (4) |
C16A—C11A—N111—C10A | 1.0 (4) | C37—C371—C376—C375 | −178.5 (3) |
C11B—C11A—N111—C10A | −177.7 (2) | C374—C375—C376—C371 | −0.3 (4) |
C22—C21—C21B—C24A | 0.9 (5) | C36A—C37—C37A—C30A | 1.7 (4) |
C22—C21—C21B—C21A | 178.9 (3) | C371—C37—C37A—C30A | −177.6 (3) |
N211—C21A—C21B—C21 | −8.5 (4) | C36A—C37—C37A—C38 | −176.5 (3) |
C26A—C21A—C21B—C21 | 169.4 (3) | C371—C37—C37A—C38 | 4.2 (6) |
N211—C21A—C21B—C24A | 169.5 (3) | C30A—C37A—C38—N39 | 0.7 (3) |
C26A—C21A—C21B—C24A | −12.7 (4) | C37—C37A—C38—N39 | 179.0 (4) |
C21B—C21—C22—C23 | 0.6 (5) | C30A—C37A—C38—C381 | −175.9 (3) |
C21—C22—C23—C24 | −0.9 (5) | C37—C37A—C38—C381 | 2.4 (6) |
C22—C23—C24—C24A | −0.3 (5) | N39—C38—C381—C382 | −108.8 (3) |
C23—C24—C24A—C21B | 1.8 (5) | C37A—C38—C381—C382 | 67.6 (4) |
C23—C24—C24A—C25 | −176.1 (3) | N39—C38—C381—C384 | 9.8 (4) |
C21—C21B—C24A—C24 | −2.1 (5) | C37A—C38—C381—C384 | −173.8 (3) |
C21A—C21B—C24A—C24 | 179.9 (3) | N39—C38—C381—C383 | 129.6 (3) |
C21—C21B—C24A—C25 | 175.9 (3) | C37A—C38—C381—C383 | −54.0 (4) |
C21A—C21B—C24A—C25 | −2.1 (4) | C37A—C38—N39—N310 | −0.2 (3) |
C24—C24A—C25—C26 | −149.8 (3) | C381—C38—N39—N310 | 177.0 (2) |
C21B—C24A—C25—C26 | 32.4 (5) | C38—N39—N310—C30A | −0.4 (3) |
C24A—C25—C26—C26A | −47.6 (4) | C38—N39—N310—C301 | 179.3 (3) |
N211—C21A—C26A—C27 | −2.3 (5) | N39—N310—C301—C302 | 152.0 (3) |
C21B—C21A—C26A—C27 | −179.9 (3) | C30A—N310—C301—C302 | −28.4 (5) |
N211—C21A—C26A—C26 | 173.8 (3) | N39—N310—C301—C306 | −25.9 (4) |
C21B—C21A—C26A—C26 | −3.9 (4) | C30A—N310—C301—C306 | 153.7 (3) |
C25—C26—C26A—C27 | −150.3 (3) | C306—C301—C302—C303 | 0.9 (5) |
C25—C26—C26A—C21A | 33.8 (4) | N310—C301—C302—C303 | −177.0 (3) |
C21A—C26A—C27—C27A | −1.9 (4) | C301—C302—C303—C304 | 0.7 (5) |
C26—C26A—C27—C27A | −177.7 (3) | C302—C303—C304—C305 | −1.2 (6) |
C21A—C26A—C27—C271 | 173.7 (3) | C303—C304—C305—C306 | 0.1 (5) |
C26—C26A—C27—C271 | −2.1 (5) | C304—C305—C306—C301 | 1.5 (5) |
C26A—C27—C271—C276 | 89.9 (4) | C302—C301—C306—C305 | −2.0 (5) |
C27A—C27—C271—C276 | −94.9 (4) | N310—C301—C306—C305 | 175.9 (3) |
C26A—C27—C271—C272 | −85.4 (4) | N39—N310—C30A—N311 | −178.9 (3) |
C27A—C27—C271—C272 | 89.8 (4) | C301—N310—C30A—N311 | 1.5 (5) |
C276—C271—C272—C273 | 1.2 (4) | N39—N310—C30A—C37A | 0.8 (3) |
C27—C271—C272—C273 | 176.8 (3) | C301—N310—C30A—C37A | −178.8 (3) |
C271—C272—C273—C274 | −1.3 (4) | C37—C37A—C30A—N311 | 0.0 (5) |
C272—C273—C274—C275 | 0.7 (5) | C38—C37A—C30A—N311 | 178.8 (3) |
C272—C273—C274—Cl27 | −178.8 (2) | C37—C37A—C30A—N310 | −179.7 (3) |
C273—C274—C275—C276 | −0.2 (5) | C38—C37A—C30A—N310 | −0.9 (3) |
Cl27—C274—C275—C276 | 179.3 (2) | N310—C30A—N311—C31A | 177.7 (3) |
C272—C271—C276—C275 | −0.7 (5) | C37A—C30A—N311—C31A | −1.9 (4) |
C27—C271—C276—C275 | −176.1 (3) | C36A—C31A—N311—C30A | 2.3 (4) |
C274—C275—C276—C271 | 0.2 (5) | C31B—C31A—N311—C30A | −177.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C173—H173···Cg2i | 0.95 | 2.62 | 3.532 (4) | 162 |
C175—H175···Cg1ii | 0.95 | 2.64 | 3.513 (4) | 153 |
C273—H273···Cg4iii | 0.95 | 2.85 | 3.687 (3) | 147 |
C375—H375···Cg3iv | 0.95 | 2.69 | 3.698 (4) | 161 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C30H26ClN3 |
Mr | 463.99 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 13.1170 (18), 15.948 (3), 17.717 (2) |
α, β, γ (°) | 93.750 (11), 91.803 (9), 101.155 (13) |
V (Å3) | 3624.7 (10) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.57 × 0.32 × 0.19 |
|
Data collection |
Diffractometer | Bruker–Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.904, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 87246, 16583, 8207 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.211, 1.05 |
No. of reflections | 16583 |
No. of parameters | 928 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.50 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C173—H173···Cg2i | 0.95 | 2.62 | 3.532 (4) | 162 |
C175—H175···Cg1ii | 0.95 | 2.64 | 3.513 (4) | 153 |
C273—H273···Cg4iii | 0.95 | 2.85 | 3.687 (3) | 147 |
C375—H375···Cg3iv | 0.95 | 2.69 | 3.698 (4) | 161 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) x+1, y, z. |
Ring-puckering parameters and selected torsion angles (°) for (I)–(III) topParameter | (I), x = 1 | (I), x = 2 | (I), x = 3 | (II) | (III) |
θ | 116.6 (4) | 116.1 (4) | 115.1 (5) | 116.6 (5) | 115.4 (2) |
ϕ | 31.1 (6) | 32.3 (5) | 30.7 (6) | 29.7 (5) | 34.1 (2) |
(pyrazole)/(Cx01-Cx06) | | | | | |
| 22.0 (2) | 28.3 (2) | 26.9 (2) | 8.3 (2) | 33.16 (8) |
(pyridine)/(Cx71-Cx76) | | | | | |
| 89.0 (2) | 89.9 (2) | 84.7 (2) | 85.9 (2) | 63.45 (7) |
The data for (II) are taken from Low et al. (2007) and the data for (III) are taken from Portilla et al. (2005); for both (II) and (II), x is nul for ring Cx71–CX76, and 1 for ring Cx01–Cx06. |
Pyrazolo[3,4-b]quinolines are of interest as possible antiviral and antimalarial agents, and because of their other biological properties, such as parasiticidic, bactericidal, vasodilator and enzyme-inhibitory activities (Quiroga et al., 2001). We report here the structure of the title compound, (I), and we compare both its conformation and its supramolecular aggregation with those of the analogous compounds (II) (Low et al., 2007), which differs from (I) in having no Cl substituent on the pendent aryl ring, and (III) (Portilla et al., 2005), which differs from (II) in having a methyl substituent in place of the tert-butyl group.
Compound (I) crystallizes with Z' = 3 in space group P1. The molecules of (I) have no internal symmetry and hence they are chiral; the asymmetric unit was selected so that all three molecules are of the same hand as defined by the torsion angles and the ring-puckering parameters (Fig. 1 and Table 1). The torsion angles between the pyrazole and pyridine rings and their pendent aryl groups show only modest variations between the three independent molecules; the corresponding values for (II) and (III) show significantly wider variation than those between the independent molecules of (I). On the other hand the ring-puckering parameters (Cremer & Pople, 1975) in (I), defined for the atom sequences Cx1A, Cx1B, Cx14A, Cx5, Cx6, Cx6A, where x takes the values 1, 2 and 3 for the three molecules, are remarkably similar to those defined by the comparable atom sequences in (II) and (III). In every case, the puckering angles are very close to the ideal values, θ = 112.5° and ϕ = (60n + 30)°, where n represents zero or an integer, for a screw-boat conformation of the non-aromatic carbocylic ring.
In each of the independent molecules of (I), as in the molecules of (II) and (III), the bond distances are consistent with aromatic delocalization within the pyridine ring and strong bond fixation in the pyrazole ring.
Although intermolecular C—H···N hydrogen bonds are absent from the structure of (I), the molecules are linked into finite multi-component aggregates by means of four independent C—H···π(arene) hydrogen bonds (Table 2). Atom C175 in the type 1 molecule (Fig. 1) at (x, y, z) acts as a hydrogen-bond donor to the pendent aryl ring (C101–C106) in the molecule at (1 − x, 1 − y, −z), so generating by inversion a centrosymmetric dimer unit, centred at (1/2, 1/2, 0). In addition, atoms C173 in the type 1 molecule at (1 − x, 1 − y, −z) and C375 in the type 3 molecule at (1 + x, y, z) act as hydrogen-bond donors, respectively, to the C21/C21B/C24A/C24/C23/C22 and C201–C206 rings, both in the type 2 molecule at (1 + x, y, z). This last pair of hydrogen bonds may be weakly reinforced by the final such interaction, involving atom C273 and the C301–C306 ring. Propagation of all these interactions by inversion then generates a centrosymmetric six-component aggregate containing two molecules of each type (Fig. 2).
###Cg1 is the centroid of the C101–C106 ring, Cg2 is the centroid of the C21/C21B/C24A/C24/C23/C22 ring, Cg3 is the centroid of the C201–C206 ring and Cg4 is the centroid of the C301–C306 ring.
The finite aggregation in compound (I), based on multiple C—H···π(arene) hydrogen bonds, may be briefly compared with the aggregation in (II) and (III), which crystallize, respectively, in space group P1 with Z' = 1 (Low et al., 2007) and P21/c with Z' = 1 (Portilla et al., 2005). In (II), pairs of molecules are linked into centrosymmetric dimers by paired C—H···π(pyridyl) hydrogen bonds, while in (III) a combination of C—H···π(arene) and C—H···π(pyridyl) hydrogen bonds links the molecules into sheets, generated by a combination of glide plane and inversion. Hence, just as the change in the hydrocarbyl substituent between compounds (I) and (II) leads to a major change in the pattern of supramolecular aggregation, so too the notional introduction of a single chloro substituent into one of the pendent aryl rings leads to significant differences between compounds (I) and (II), both in respect of the crystallization characteristics as manifested by the Z" values, and in the nature of the supramolecular aggregation.