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The title compound, C30H26ClN3, crystallizes with Z' = 3 in the P\overline{1} 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...[pi](arene) hydrogen bonds link the mol­ecules into centrosymmetric six-component aggregates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107041236/sk3154sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107041236/sk3154Isup2.hkl
Contains datablock I

CCDC reference: 665504

Comment top

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.

Related literature top

For related literature, see: Cremer & Pople (1975); Low et al. (2007); Portilla et al. (2005); Quiroga et al. (2001); Spek (2003).

Experimental top

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).

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
Figure 1. The three independent molecules in compound (I) showing the atom-labelling schemes: (a) a type 1 molecule, (b) a type 2 molecule, and (c) a type 3 molecule. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2. A stereoview of part of the crystal structure of compound (I) showing the formation of a centrosymmetric six-component aggregate containing four independent C—H···π(arene) hydrogen bonds.
8-tert-Butyl-7-(4-chlorophenyl)-10-phenyl-5,6-dihydro-10H- benzo[h]pyrazolo[3,4-b]quinoline top
Crystal data top
C30H26ClN3Z = 6
Mr = 463.99F(000) = 1464
Triclinic, P1Dx = 1.275 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.1170 (18) ÅCell parameters from 16583 reflections
b = 15.948 (3) Åθ = 3.1–27.5°
c = 17.717 (2) ŵ = 0.18 mm1
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 anode8207 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 2020
Tmin = 0.904, Tmax = 0.966l = 2223
87246 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H-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 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
C30H26ClN3γ = 101.155 (13)°
Mr = 463.99V = 3624.7 (10) Å3
Triclinic, P1Z = 6
a = 13.1170 (18) ÅMo Kα radiation
b = 15.948 (3) ŵ = 0.18 mm1
c = 17.717 (2) ÅT = 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 = 0.966Rint = 0.074
87246 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.211H-atom parameters constrained
S = 1.05Δρmax = 0.53 e Å3
16583 reflectionsΔρmin = 0.50 e Å3
928 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.2842 (2)0.28521 (19)0.26343 (17)0.0336 (7)
C11A0.3019 (2)0.39781 (18)0.17080 (16)0.0278 (7)
C11B0.2973 (2)0.37154 (18)0.24913 (16)0.0296 (7)
C120.2804 (3)0.2614 (2)0.33720 (17)0.0371 (8)
C130.2897 (3)0.3224 (2)0.39680 (17)0.0418 (8)
C140.3036 (3)0.4079 (2)0.38313 (18)0.0416 (8)
C14A0.3080 (3)0.4331 (2)0.30955 (17)0.0377 (8)
C150.3288 (3)0.5256 (2)0.29332 (19)0.0553 (10)
C160.2801 (3)0.5420 (2)0.22150 (18)0.0416 (8)
C16A0.2967 (2)0.48331 (18)0.15563 (16)0.0302 (7)
C170.3039 (2)0.50883 (18)0.08181 (16)0.0289 (7)
C1710.2987 (2)0.59974 (18)0.06959 (16)0.0293 (7)
C1720.2035 (3)0.6225 (2)0.0572 (2)0.0459 (9)
C1730.1970 (3)0.7072 (2)0.0471 (2)0.0467 (9)
C1740.2856 (3)0.76843 (18)0.04960 (17)0.0339 (7)
Cl170.27739 (7)0.87348 (5)0.03488 (5)0.0477 (2)
C1750.3811 (3)0.74815 (19)0.06426 (18)0.0402 (8)
C1760.3869 (2)0.66339 (19)0.07374 (18)0.0366 (8)
C17A0.3174 (2)0.44704 (17)0.02394 (16)0.0270 (6)
C180.3305 (2)0.43850 (18)0.05703 (16)0.0299 (7)
C1810.3366 (2)0.50077 (18)0.11905 (16)0.0327 (7)
C1820.4315 (3)0.5727 (2)0.1027 (2)0.0506 (10)
C1830.2389 (3)0.5377 (2)0.1267 (2)0.0558 (10)
C1840.3511 (4)0.4549 (2)0.19492 (19)0.0674 (13)
N190.34144 (19)0.35993 (15)0.07791 (13)0.0301 (6)
N1100.33591 (19)0.31392 (14)0.01506 (12)0.0275 (6)
C1010.3492 (2)0.22776 (17)0.02256 (16)0.0280 (7)
C1020.3824 (2)0.18890 (19)0.03879 (17)0.0337 (7)
C1030.3977 (3)0.10535 (19)0.02867 (17)0.0357 (8)
C1040.3826 (3)0.06150 (19)0.04139 (17)0.0369 (8)
C1050.3493 (3)0.10065 (18)0.10236 (17)0.0363 (8)
C1060.3323 (2)0.18357 (18)0.09318 (17)0.0335 (7)
C10A0.3209 (2)0.36435 (18)0.04747 (15)0.0265 (6)
N1110.31324 (18)0.33805 (14)0.11708 (13)0.0270 (5)
C210.0508 (2)0.3494 (2)0.05326 (17)0.0345 (7)
C21A0.0368 (2)0.24276 (19)0.15120 (16)0.0303 (7)
C21B0.0508 (2)0.2662 (2)0.07218 (16)0.0320 (7)
C220.0657 (2)0.3717 (2)0.02016 (18)0.0396 (8)
C230.0800 (3)0.3101 (2)0.07592 (18)0.0427 (8)
C240.0806 (3)0.2277 (2)0.05726 (18)0.0441 (9)
C24A0.0676 (2)0.2041 (2)0.01688 (17)0.0371 (8)
C250.0745 (3)0.1176 (2)0.03925 (19)0.0489 (9)
C260.0091 (3)0.0894 (2)0.10276 (18)0.0456 (9)
C26A0.0193 (2)0.15527 (19)0.16810 (17)0.0333 (7)
C270.0060 (2)0.13368 (18)0.24289 (17)0.0304 (7)
C2710.0231 (2)0.04111 (18)0.25685 (16)0.0310 (7)
C2720.1277 (2)0.00160 (19)0.25123 (17)0.0339 (7)
C2730.1587 (2)0.08543 (18)0.26001 (17)0.0336 (7)
C2740.0842 (2)0.13339 (18)0.27303 (16)0.0307 (7)
Cl270.12306 (7)0.24287 (5)0.28226 (5)0.0448 (2)
C2750.0203 (3)0.0964 (2)0.27831 (18)0.0387 (8)
C2760.0498 (3)0.00897 (19)0.26999 (17)0.0358 (7)
C27A0.0136 (2)0.20129 (17)0.29989 (16)0.0265 (6)
C280.0076 (2)0.21547 (18)0.38099 (16)0.0292 (7)
C2810.0008 (2)0.15638 (18)0.44531 (16)0.0323 (7)
C2820.0961 (3)0.1165 (2)0.45083 (19)0.0450 (9)
C2830.0986 (3)0.0869 (2)0.4353 (2)0.0449 (9)
C2840.0065 (3)0.2082 (2)0.52018 (18)0.0499 (10)
N290.0140 (2)0.29819 (15)0.40004 (13)0.0312 (6)
N2100.02456 (19)0.34045 (14)0.33484 (13)0.0288 (6)
C2010.0258 (2)0.42974 (18)0.33871 (17)0.0298 (7)
C2020.0126 (2)0.46670 (18)0.27823 (17)0.0342 (7)
C2030.0134 (3)0.55394 (19)0.28436 (18)0.0406 (8)
C2040.0215 (3)0.60284 (19)0.35049 (18)0.0417 (8)
C2050.0590 (3)0.56554 (19)0.41036 (19)0.0447 (9)
C2060.0626 (3)0.47911 (19)0.40486 (18)0.0390 (8)
C20A0.0263 (2)0.28428 (18)0.27356 (16)0.0286 (7)
N2110.03805 (19)0.30737 (15)0.20312 (13)0.0293 (6)
C310.6352 (3)0.0144 (2)0.63928 (18)0.0376 (8)
C31A0.6558 (2)0.09495 (18)0.54326 (17)0.0318 (7)
C31B0.6647 (2)0.07042 (19)0.62183 (17)0.0316 (7)
C320.6439 (3)0.0367 (2)0.71302 (19)0.0420 (8)
C330.6829 (3)0.0256 (2)0.77036 (19)0.0406 (8)
C340.7133 (3)0.1098 (2)0.75361 (18)0.0400 (8)
C34A0.7055 (2)0.13333 (19)0.67987 (18)0.0362 (7)
C350.7414 (3)0.2229 (2)0.65938 (19)0.0492 (9)
C360.6841 (3)0.2475 (2)0.59451 (18)0.0436 (8)
C36A0.6671 (2)0.18215 (19)0.52864 (17)0.0343 (7)
C370.6599 (2)0.20524 (18)0.45423 (17)0.0303 (7)
C3710.6687 (3)0.29774 (19)0.44063 (17)0.0342 (7)
C3720.5829 (3)0.3363 (2)0.4466 (2)0.0482 (9)
C3730.5907 (3)0.4225 (2)0.4349 (2)0.0523 (10)
C3740.6858 (3)0.47029 (19)0.41840 (17)0.0411 (9)
Cl370.69703 (10)0.57825 (5)0.40401 (5)0.0657 (3)
C3750.7719 (3)0.43434 (19)0.41418 (17)0.0391 (8)
C3760.7631 (3)0.34802 (18)0.42517 (16)0.0323 (7)
C37A0.6435 (2)0.13884 (18)0.39540 (17)0.0300 (7)
C380.6352 (2)0.12695 (18)0.31329 (17)0.0312 (7)
C3810.6452 (3)0.18850 (18)0.25007 (17)0.0353 (7)
C3820.7568 (3)0.2369 (2)0.24799 (19)0.0412 (8)
C3830.5722 (3)0.2525 (2)0.2613 (2)0.0525 (10)
C3840.6164 (3)0.1374 (2)0.17421 (19)0.0543 (10)
N390.6202 (2)0.04405 (15)0.29159 (14)0.0329 (6)
N3100.61851 (19)0.00013 (15)0.35535 (14)0.0317 (6)
C3010.6022 (2)0.09084 (17)0.34717 (17)0.0305 (7)
C3020.6421 (3)0.13599 (19)0.40131 (18)0.0406 (8)
C3030.6289 (3)0.2242 (2)0.3898 (2)0.0474 (9)
C3040.5778 (3)0.2671 (2)0.32496 (19)0.0431 (8)
C3050.5379 (3)0.22144 (19)0.27190 (18)0.0377 (8)
C3060.5486 (2)0.13372 (19)0.28295 (17)0.0327 (7)
C30A0.6332 (2)0.05518 (18)0.41896 (17)0.0310 (7)
N3110.63699 (19)0.03055 (15)0.48924 (14)0.0307 (6)
H110.27790.24270.22250.040*
H120.27140.20260.34670.045*
H130.28650.30570.44730.050*
H140.31040.44990.42440.050*
H15A0.30300.55900.33510.066*
H15B0.40490.54620.29220.066*
H16A0.30810.60180.21010.050*
H16B0.20440.53660.22770.050*
H1720.14180.57990.05560.055*
H1730.13120.72220.03850.056*
H1750.44240.79150.06790.048*
H1760.45280.64890.08330.044*
H18A0.42070.60820.05760.076*
H18B0.44150.60810.14610.076*
H18C0.49330.54790.09410.076*
H18D0.17810.49090.13400.084*
H18E0.24330.57270.17040.084*
H18F0.23210.57340.08070.084*
H18G0.29440.40510.20510.101*
H18H0.41780.43600.19340.101*
H18I0.35020.49420.23510.101*
H1020.39460.21910.08720.040*
H1030.41890.07800.07080.043*
H1040.39490.00480.04790.044*
H1050.33810.07040.15080.044*
H1060.30910.21010.13520.040*
H210.04040.39140.09130.041*
H220.06620.42890.03250.047*
H230.08930.32480.12670.051*
H240.09000.18590.09580.053*
H25A0.05360.07600.00510.059*
H25B0.14780.11690.05370.059*
H26A0.02830.03680.12070.055*
H26B0.06460.07470.08410.055*
H2720.17880.03470.24120.041*
H2730.23040.11150.25710.040*
H2750.07110.13010.28740.046*
H2760.12150.01690.27340.043*
H28A0.10200.08290.40340.067*
H28B0.09040.07900.49280.067*
H28C0.15800.16200.45980.067*
H28D0.15810.11270.42170.067*
H28E0.11120.05910.48280.067*
H28F0.08960.04430.39500.067*
H28G0.05580.25340.52820.075*
H28H0.01070.17030.56180.075*
H28I0.06840.23410.51850.075*
H2020.03810.43290.23300.041*
H2030.03830.58000.24270.049*
H2040.01960.66220.35460.050*
H2050.08270.59930.45600.054*
H2060.09000.45390.44610.047*
H310.60890.05750.60020.045*
H320.62310.09480.72440.050*
H330.68860.01040.82100.049*
H340.73990.15240.79310.048*
H35A0.73570.26230.70390.059*
H35B0.81590.23070.64790.059*
H36A0.72300.30220.57790.052*
H36B0.61570.25720.61100.052*
H3720.51790.30340.45880.058*
H3730.53140.44840.43830.063*
H3750.83730.46810.40380.047*
H3760.82290.32290.42200.039*
H38A0.76270.27480.20630.062*
H38B0.80310.19590.24030.062*
H38C0.77660.27110.29600.062*
H38D0.50240.22150.27110.079*
H38E0.56920.28340.21550.079*
H38F0.59850.29340.30450.079*
H38G0.61750.17690.13400.081*
H38H0.54650.10230.17570.081*
H38I0.66650.10030.16420.081*
H3020.67810.10680.44580.049*
H3030.65540.25570.42700.057*
H3040.57030.32750.31710.052*
H3050.50260.25060.22720.045*
H3060.51940.10280.24670.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0397 (19)0.0341 (18)0.0287 (17)0.0109 (14)0.0024 (14)0.0029 (14)
C11A0.0266 (16)0.0296 (16)0.0250 (16)0.0013 (13)0.0010 (12)0.0007 (13)
C11B0.0283 (17)0.0325 (17)0.0265 (16)0.0024 (13)0.0031 (13)0.0004 (13)
C120.046 (2)0.0355 (18)0.0319 (18)0.0110 (15)0.0047 (15)0.0077 (15)
C130.051 (2)0.055 (2)0.0214 (17)0.0134 (17)0.0061 (15)0.0080 (15)
C140.055 (2)0.043 (2)0.0256 (18)0.0074 (17)0.0034 (15)0.0032 (15)
C14A0.042 (2)0.0379 (18)0.0312 (18)0.0041 (15)0.0040 (14)0.0009 (15)
C150.096 (3)0.0333 (19)0.032 (2)0.0043 (19)0.0091 (19)0.0048 (15)
C160.055 (2)0.0314 (18)0.038 (2)0.0095 (16)0.0060 (16)0.0009 (15)
C16A0.0349 (18)0.0249 (16)0.0298 (17)0.0047 (13)0.0035 (13)0.0021 (13)
C170.0287 (17)0.0270 (16)0.0299 (17)0.0022 (13)0.0012 (13)0.0029 (13)
C1710.0352 (18)0.0245 (15)0.0264 (16)0.0014 (13)0.0024 (13)0.0017 (12)
C1720.039 (2)0.0312 (18)0.064 (2)0.0013 (15)0.0036 (17)0.0021 (17)
C1730.041 (2)0.0329 (19)0.066 (2)0.0082 (16)0.0082 (18)0.0032 (17)
C1740.047 (2)0.0239 (16)0.0297 (17)0.0033 (14)0.0036 (14)0.0014 (13)
Cl170.0701 (6)0.0273 (4)0.0466 (5)0.0103 (4)0.0058 (4)0.0071 (4)
C1750.039 (2)0.0284 (17)0.049 (2)0.0037 (15)0.0060 (16)0.0004 (15)
C1760.0315 (18)0.0332 (18)0.044 (2)0.0045 (14)0.0031 (14)0.0022 (15)
C17A0.0298 (17)0.0246 (15)0.0248 (16)0.0011 (12)0.0002 (12)0.0016 (12)
C180.0300 (17)0.0281 (16)0.0288 (17)0.0007 (13)0.0033 (13)0.0038 (13)
C1810.045 (2)0.0263 (16)0.0253 (16)0.0035 (14)0.0015 (14)0.0039 (13)
C1820.049 (2)0.046 (2)0.050 (2)0.0103 (17)0.0061 (17)0.0218 (18)
C1830.045 (2)0.068 (3)0.058 (2)0.0103 (19)0.0006 (18)0.033 (2)
C1840.137 (4)0.039 (2)0.029 (2)0.022 (2)0.010 (2)0.0102 (17)
N190.0377 (15)0.0284 (14)0.0229 (13)0.0028 (11)0.0011 (11)0.0061 (11)
N1100.0390 (15)0.0225 (12)0.0200 (13)0.0036 (11)0.0001 (10)0.0026 (10)
C1010.0351 (18)0.0217 (15)0.0255 (16)0.0010 (13)0.0026 (13)0.0021 (12)
C1020.044 (2)0.0317 (17)0.0232 (16)0.0025 (14)0.0020 (14)0.0008 (13)
C1030.049 (2)0.0291 (17)0.0286 (17)0.0061 (15)0.0027 (14)0.0051 (14)
C1040.050 (2)0.0234 (16)0.0359 (19)0.0046 (14)0.0008 (15)0.0011 (14)
C1050.050 (2)0.0268 (17)0.0288 (17)0.0009 (15)0.0003 (15)0.0032 (13)
C1060.044 (2)0.0282 (16)0.0267 (17)0.0023 (14)0.0001 (14)0.0024 (13)
C10A0.0287 (17)0.0280 (16)0.0206 (15)0.0000 (13)0.0001 (12)0.0023 (12)
N1110.0308 (14)0.0264 (13)0.0220 (13)0.0012 (11)0.0019 (10)0.0010 (10)
C210.0327 (18)0.0391 (18)0.0285 (17)0.0002 (14)0.0001 (13)0.0016 (14)
C21A0.0294 (17)0.0313 (17)0.0283 (17)0.0030 (13)0.0017 (13)0.0023 (13)
C21B0.0279 (17)0.0407 (18)0.0249 (16)0.0011 (14)0.0004 (13)0.0006 (14)
C220.040 (2)0.043 (2)0.0319 (18)0.0025 (15)0.0008 (15)0.0068 (15)
C230.041 (2)0.056 (2)0.0271 (18)0.0006 (17)0.0048 (15)0.0061 (16)
C240.046 (2)0.051 (2)0.0333 (19)0.0058 (17)0.0082 (15)0.0029 (16)
C24A0.0388 (19)0.0427 (19)0.0280 (17)0.0047 (15)0.0057 (14)0.0023 (14)
C250.072 (3)0.040 (2)0.0335 (19)0.0104 (18)0.0106 (18)0.0057 (15)
C260.064 (2)0.0346 (19)0.036 (2)0.0051 (17)0.0085 (17)0.0024 (15)
C26A0.0408 (19)0.0303 (17)0.0287 (17)0.0075 (14)0.0053 (14)0.0021 (13)
C270.0328 (18)0.0266 (16)0.0318 (17)0.0061 (13)0.0005 (13)0.0012 (13)
C2710.0369 (19)0.0263 (16)0.0300 (17)0.0079 (14)0.0024 (13)0.0017 (13)
C2720.0344 (19)0.0320 (17)0.0361 (18)0.0099 (14)0.0009 (14)0.0002 (14)
C2730.0358 (18)0.0295 (17)0.0344 (18)0.0045 (14)0.0016 (14)0.0004 (14)
C2740.043 (2)0.0225 (15)0.0269 (16)0.0070 (14)0.0011 (13)0.0008 (12)
Cl270.0620 (6)0.0261 (4)0.0453 (5)0.0063 (4)0.0002 (4)0.0035 (4)
C2750.039 (2)0.0377 (19)0.042 (2)0.0146 (15)0.0021 (15)0.0038 (15)
C2760.0349 (19)0.0312 (17)0.0415 (19)0.0080 (14)0.0015 (15)0.0006 (14)
C27A0.0312 (17)0.0239 (15)0.0257 (16)0.0082 (13)0.0005 (12)0.0031 (12)
C280.0302 (17)0.0276 (16)0.0296 (17)0.0055 (13)0.0020 (13)0.0003 (13)
C2810.046 (2)0.0254 (16)0.0265 (16)0.0081 (14)0.0029 (14)0.0053 (13)
C2820.052 (2)0.045 (2)0.040 (2)0.0135 (17)0.0030 (16)0.0130 (16)
C2830.049 (2)0.0391 (19)0.048 (2)0.0065 (16)0.0059 (17)0.0184 (16)
C2840.089 (3)0.0350 (19)0.0293 (19)0.0168 (19)0.0062 (18)0.0111 (15)
N290.0428 (16)0.0271 (14)0.0240 (13)0.0073 (12)0.0004 (11)0.0033 (11)
N2100.0406 (15)0.0238 (13)0.0216 (13)0.0051 (11)0.0004 (11)0.0026 (10)
C2010.0362 (18)0.0219 (15)0.0309 (17)0.0039 (13)0.0021 (13)0.0045 (13)
C2020.049 (2)0.0283 (16)0.0247 (16)0.0074 (14)0.0033 (14)0.0016 (13)
C2030.059 (2)0.0308 (18)0.0347 (19)0.0139 (16)0.0038 (16)0.0069 (15)
C2040.061 (2)0.0230 (16)0.041 (2)0.0110 (16)0.0057 (17)0.0008 (15)
C2050.066 (2)0.0278 (17)0.0360 (19)0.0041 (16)0.0169 (17)0.0043 (14)
C2060.054 (2)0.0293 (17)0.0327 (18)0.0069 (15)0.0058 (15)0.0021 (14)
C20A0.0327 (17)0.0269 (16)0.0256 (16)0.0058 (13)0.0013 (13)0.0019 (13)
N2110.0349 (15)0.0286 (13)0.0224 (13)0.0024 (11)0.0008 (11)0.0001 (11)
C310.046 (2)0.0324 (18)0.0330 (18)0.0044 (15)0.0050 (15)0.0002 (14)
C31A0.0297 (17)0.0290 (17)0.0353 (18)0.0033 (13)0.0068 (14)0.0026 (14)
C31B0.0324 (18)0.0304 (17)0.0327 (17)0.0066 (14)0.0081 (13)0.0028 (13)
C320.046 (2)0.0347 (18)0.045 (2)0.0059 (16)0.0095 (16)0.0108 (16)
C330.040 (2)0.047 (2)0.0363 (19)0.0102 (16)0.0088 (15)0.0066 (16)
C340.041 (2)0.046 (2)0.0331 (19)0.0096 (16)0.0044 (15)0.0024 (15)
C34A0.0397 (19)0.0331 (17)0.0352 (19)0.0059 (15)0.0084 (14)0.0014 (14)
C350.068 (3)0.038 (2)0.038 (2)0.0046 (18)0.0053 (18)0.0026 (16)
C360.061 (2)0.0306 (18)0.038 (2)0.0059 (16)0.0114 (17)0.0009 (15)
C36A0.0372 (19)0.0301 (17)0.0353 (18)0.0065 (14)0.0066 (14)0.0015 (14)
C370.0294 (17)0.0234 (15)0.0379 (18)0.0043 (13)0.0041 (13)0.0024 (13)
C3710.044 (2)0.0283 (16)0.0322 (18)0.0118 (15)0.0021 (14)0.0008 (13)
C3720.045 (2)0.040 (2)0.064 (2)0.0181 (17)0.0075 (18)0.0002 (18)
C3730.065 (3)0.044 (2)0.055 (2)0.032 (2)0.002 (2)0.0046 (18)
C3740.074 (3)0.0262 (17)0.0251 (17)0.0160 (18)0.0014 (16)0.0013 (13)
Cl370.1333 (10)0.0290 (5)0.0401 (5)0.0305 (5)0.0054 (5)0.0012 (4)
C3750.058 (2)0.0284 (17)0.0289 (18)0.0047 (16)0.0004 (15)0.0006 (14)
C3760.044 (2)0.0263 (16)0.0261 (16)0.0073 (14)0.0004 (14)0.0004 (13)
C37A0.0311 (17)0.0262 (16)0.0331 (17)0.0060 (13)0.0003 (13)0.0052 (13)
C380.0303 (17)0.0256 (16)0.0377 (18)0.0057 (13)0.0008 (13)0.0028 (13)
C3810.045 (2)0.0248 (16)0.0353 (18)0.0053 (14)0.0008 (15)0.0042 (13)
C3820.047 (2)0.0344 (18)0.0400 (19)0.0014 (16)0.0037 (16)0.0040 (15)
C3830.051 (2)0.046 (2)0.065 (3)0.0155 (18)0.0032 (19)0.0239 (19)
C3840.080 (3)0.040 (2)0.037 (2)0.0028 (19)0.0195 (19)0.0100 (16)
N390.0403 (16)0.0272 (14)0.0313 (14)0.0060 (12)0.0024 (12)0.0054 (11)
N3100.0380 (15)0.0267 (13)0.0298 (14)0.0055 (11)0.0029 (11)0.0024 (11)
C3010.0373 (18)0.0207 (15)0.0338 (17)0.0061 (13)0.0039 (14)0.0011 (13)
C3020.056 (2)0.0327 (18)0.0332 (18)0.0137 (16)0.0087 (16)0.0029 (14)
C3030.074 (3)0.0303 (18)0.042 (2)0.0199 (18)0.0026 (18)0.0044 (16)
C3040.062 (2)0.0232 (16)0.044 (2)0.0108 (16)0.0021 (17)0.0030 (15)
C3050.045 (2)0.0296 (17)0.0356 (18)0.0026 (15)0.0007 (15)0.0049 (14)
C3060.0343 (18)0.0329 (17)0.0302 (17)0.0041 (14)0.0023 (13)0.0050 (14)
C30A0.0334 (18)0.0273 (16)0.0307 (17)0.0039 (13)0.0022 (13)0.0038 (13)
N3110.0347 (15)0.0271 (13)0.0300 (14)0.0045 (11)0.0038 (11)0.0024 (11)
Geometric parameters (Å, º) top
C11—C121.384 (4)C276—H2760.95
C11—C11B1.395 (4)C27A—C20A1.413 (4)
C11—H110.95C27A—C281.447 (4)
C11A—N1111.335 (3)C28—N291.326 (4)
C11A—C16A1.421 (4)C28—C2811.519 (4)
C11A—C11B1.475 (4)C281—C2831.522 (4)
C11B—C14A1.389 (4)C281—C2841.528 (4)
C12—C131.374 (4)C281—C2821.530 (4)
C12—H120.95C282—H28A0.98
C13—C141.378 (4)C282—H28B0.98
C13—H130.95C282—H28C0.98
C14—C14A1.389 (4)C283—H28D0.98
C14—H140.95C283—H28E0.98
C14A—C151.495 (4)C283—H28F0.98
C15—C161.468 (5)C284—H28G0.98
C15—H15A0.99C284—H28H0.98
C15—H15B0.99C284—H28I0.98
C16—C16A1.496 (4)N29—N2101.372 (3)
C16—H16A0.99N210—C20A1.365 (3)
C16—H16B0.99N210—C2011.418 (3)
C16A—C171.396 (4)C201—C2021.383 (4)
C17—C17A1.414 (4)C201—C2061.387 (4)
C17—C1711.494 (4)C202—C2031.391 (4)
C171—C1721.380 (4)C202—H2020.95
C171—C1761.380 (4)C203—C2041.378 (4)
C172—C1731.392 (4)C203—H2030.95
C172—H1720.95C204—C2051.372 (4)
C173—C1741.363 (4)C204—H2040.95
C173—H1730.95C205—C2061.385 (4)
C174—C1751.375 (4)C205—H2050.95
C174—Cl171.735 (3)C206—H2060.95
C175—C1761.389 (4)C20A—N2111.329 (4)
C175—H1750.95C31—C321.383 (4)
C176—H1760.95C31—C31B1.392 (4)
C17A—C10A1.418 (4)C31—H310.95
C17A—C181.451 (4)C31A—N3111.338 (4)
C18—N191.319 (4)C31A—C36A1.412 (4)
C18—C1811.522 (4)C31A—C31B1.478 (4)
C181—C1831.517 (5)C31B—C34A1.405 (4)
C181—C1841.523 (4)C32—C331.385 (5)
C181—C1821.527 (4)C32—H320.95
C182—H18A0.98C33—C341.380 (4)
C182—H18B0.98C33—H330.95
C182—H18C0.98C34—C34A1.388 (4)
C183—H18D0.98C34—H340.95
C183—H18E0.98C34A—C351.487 (4)
C183—H18F0.98C35—C361.469 (5)
C184—H18G0.98C35—H35A0.99
C184—H18H0.98C35—H35B0.99
C184—H18I0.98C36—C36A1.494 (4)
N19—N1101.369 (3)C36—H36A0.99
N110—C10A1.368 (3)C36—H36B0.99
N110—C1011.416 (3)C36A—C371.397 (4)
C101—C1061.385 (4)C37—C37A1.417 (4)
C101—C1021.385 (4)C37—C3711.493 (4)
C102—C1031.386 (4)C371—C3761.384 (4)
C102—H1020.95C371—C3721.388 (4)
C103—C1041.373 (4)C372—C3731.388 (5)
C103—H1030.95C372—H3720.95
C104—C1051.382 (4)C373—C3741.381 (5)
C104—H1040.95C373—H3730.95
C105—C1061.383 (4)C374—C3751.364 (5)
C105—H1050.95C374—Cl371.736 (3)
C106—H1060.95C375—C3761.386 (4)
C10A—N1111.329 (3)C375—H3750.95
C21—C221.381 (4)C376—H3760.95
C21—C21B1.391 (4)C37A—C30A1.407 (4)
C21—H210.95C37A—C381.453 (4)
C21A—N2111.333 (4)C38—N391.328 (4)
C21A—C26A1.423 (4)C38—C3811.529 (4)
C21A—C21B1.480 (4)C381—C3821.520 (4)
C21B—C24A1.399 (4)C381—C3841.523 (4)
C22—C231.390 (4)C381—C3831.536 (4)
C22—H220.95C382—H38A0.98
C23—C241.378 (4)C382—H38B0.98
C23—H230.95C382—H38C0.98
C24—C24A1.396 (4)C383—H38D0.98
C24—H240.95C383—H38E0.98
C24A—C251.478 (4)C383—H38F0.98
C25—C261.477 (5)C384—H38G0.98
C25—H25A0.99C384—H38H0.98
C25—H25B0.99C384—H38I0.98
C26—C26A1.496 (4)N39—N3101.369 (3)
C26—H26A0.99N310—C30A1.370 (4)
C26—H26B0.99N310—C3011.418 (3)
C26A—C271.399 (4)C301—C3021.385 (4)
C27—C27A1.415 (4)C301—C3061.385 (4)
C27—C2711.491 (4)C302—C3031.385 (4)
C271—C2761.383 (4)C302—H3020.95
C271—C2721.392 (4)C303—C3041.381 (5)
C272—C2731.389 (4)C303—H3030.95
C272—H2720.95C304—C3051.376 (4)
C273—C2741.374 (4)C304—H3040.95
C273—H2730.95C305—C3061.379 (4)
C274—C2751.381 (4)C305—H3050.95
C274—Cl271.741 (3)C306—H3060.95
C275—C2761.392 (4)C30A—N3111.332 (4)
C275—H2750.95
C12—C11—C11B120.1 (3)C20A—C27A—C27115.3 (3)
C12—C11—H11120.0C20A—C27A—C28104.1 (2)
C11B—C11—H11120.0C27—C27A—C28140.5 (3)
N111—C11A—C16A123.2 (3)N29—C28—C27A110.2 (2)
N111—C11A—C11B116.5 (2)N29—C28—C281116.7 (3)
C16A—C11A—C11B120.3 (3)C27A—C28—C281133.1 (3)
C14A—C11B—C11119.4 (3)C28—C281—C283111.3 (2)
C14A—C11B—C11A120.0 (3)C28—C281—C284109.4 (2)
C11—C11B—C11A120.6 (3)C283—C281—C284107.7 (3)
C13—C12—C11120.4 (3)C28—C281—C282110.1 (3)
C13—C12—H12119.8C283—C281—C282110.6 (3)
C11—C12—H12119.8C284—C281—C282107.6 (3)
C12—C13—C14119.8 (3)C281—C282—H28A109.5
C12—C13—H13120.1C281—C282—H28B109.5
C14—C13—H13120.1H28A—C282—H28B109.5
C13—C14—C14A120.7 (3)C281—C282—H28C109.5
C13—C14—H14119.7H28A—C282—H28C109.5
C14A—C14—H14119.7H28B—C282—H28C109.5
C14—C14A—C11B119.6 (3)C281—C283—H28D109.5
C14—C14A—C15121.7 (3)C281—C283—H28E109.5
C11B—C14A—C15118.6 (3)H28D—C283—H28E109.5
C16—C15—C14A113.6 (3)C281—C283—H28F109.5
C16—C15—H15A108.8H28D—C283—H28F109.5
C14A—C15—H15A108.8H28E—C283—H28F109.5
C16—C15—H15B108.8C281—C284—H28G109.5
C14A—C15—H15B108.8C281—C284—H28H109.5
H15A—C15—H15B107.7H28G—C284—H28H109.5
C15—C16—C16A114.2 (3)C281—C284—H28I109.5
C15—C16—H16A108.7H28G—C284—H28I109.5
C16A—C16—H16A108.7H28H—C284—H28I109.5
C15—C16—H16B108.7C28—N29—N210107.6 (2)
C16A—C16—H16B108.7C20A—N210—N29110.6 (2)
H16A—C16—H16B107.6C20A—N210—C201130.1 (2)
C17—C16A—C11A120.3 (3)N29—N210—C201119.1 (2)
C17—C16A—C16122.7 (3)C202—C201—C206120.3 (3)
C11A—C16A—C16116.9 (3)C202—C201—N210120.4 (3)
C16A—C17—C17A117.6 (3)C206—C201—N210119.2 (3)
C16A—C17—C171117.8 (3)C201—C202—C203119.3 (3)
C17A—C17—C171124.6 (3)C201—C202—H202120.4
C172—C171—C176118.3 (3)C203—C202—H202120.4
C172—C171—C17120.0 (3)C204—C203—C202120.5 (3)
C176—C171—C17121.6 (3)C204—C203—H203119.8
C171—C172—C173120.8 (3)C202—C203—H203119.8
C171—C172—H172119.6C205—C204—C203119.8 (3)
C173—C172—H172119.6C205—C204—H204120.1
C174—C173—C172119.6 (3)C203—C204—H204120.1
C174—C173—H173120.2C204—C205—C206120.6 (3)
C172—C173—H173120.2C204—C205—H205119.7
C173—C174—C175120.9 (3)C206—C205—H205119.7
C173—C174—Cl17119.5 (3)C205—C206—C201119.5 (3)
C175—C174—Cl17119.6 (2)C205—C206—H206120.3
C174—C175—C176119.0 (3)C201—C206—H206120.3
C174—C175—H175120.5N211—C20A—N210123.9 (3)
C176—C175—H175120.5N211—C20A—C27A128.6 (3)
C171—C176—C175121.3 (3)N210—C20A—C27A107.5 (2)
C171—C176—H176119.3C20A—N211—C21A114.7 (2)
C175—C176—H176119.3C32—C31—C31B120.6 (3)
C17—C17A—C10A115.8 (2)C32—C31—H31119.7
C17—C17A—C18140.6 (3)C31B—C31—H31119.7
C10A—C17A—C18103.7 (2)N311—C31A—C36A123.7 (3)
N19—C18—C17A110.1 (2)N311—C31A—C31B116.2 (3)
N19—C18—C181116.5 (3)C36A—C31A—C31B120.1 (3)
C17A—C18—C181133.4 (3)C31—C31B—C34A119.2 (3)
C183—C181—C18112.3 (3)C31—C31B—C31A121.1 (3)
C183—C181—C184107.7 (3)C34A—C31B—C31A119.7 (3)
C18—C181—C184109.8 (2)C31—C32—C33120.1 (3)
C183—C181—C182110.2 (3)C31—C32—H32120.0
C18—C181—C182109.3 (2)C33—C32—H32120.0
C184—C181—C182107.3 (3)C34—C33—C32119.8 (3)
C181—C182—H18A109.5C34—C33—H33120.1
C181—C182—H18B109.5C32—C33—H33120.1
H18A—C182—H18B109.5C33—C34—C34A120.9 (3)
C181—C182—H18C109.5C33—C34—H34119.5
H18A—C182—H18C109.5C34A—C34—H34119.5
H18B—C182—H18C109.5C34—C34A—C31B119.3 (3)
C181—C183—H18D109.5C34—C34A—C35122.3 (3)
C181—C183—H18E109.5C31B—C34A—C35118.3 (3)
H18D—C183—H18E109.5C36—C35—C34A114.9 (3)
C181—C183—H18F109.5C36—C35—H35A108.6
H18D—C183—H18F109.5C34A—C35—H35A108.6
H18E—C183—H18F109.5C36—C35—H35B108.6
C181—C184—H18G109.5C34A—C35—H35B108.6
C181—C184—H18H109.5H35A—C35—H35B107.5
H18G—C184—H18H109.5C35—C36—C36A113.7 (3)
C181—C184—H18I109.5C35—C36—H36A108.8
H18G—C184—H18I109.5C36A—C36—H36A108.8
H18H—C184—H18I109.5C35—C36—H36B108.8
C18—N19—N110108.3 (2)C36A—C36—H36B108.8
C10A—N110—N19110.1 (2)H36A—C36—H36B107.7
C10A—N110—C101130.8 (2)C37—C36A—C31A120.0 (3)
N19—N110—C101119.0 (2)C37—C36A—C36121.8 (3)
C106—C101—C102120.1 (3)C31A—C36A—C36118.2 (3)
C106—C101—N110118.9 (2)C36A—C37—C37A117.8 (3)
C102—C101—N110120.9 (3)C36A—C37—C371118.8 (3)
C101—C102—C103119.2 (3)C37A—C37—C371123.4 (3)
C101—C102—H102120.4C376—C371—C372118.3 (3)
C103—C102—H102120.4C376—C371—C37121.2 (3)
C104—C103—C102121.0 (3)C372—C371—C37120.5 (3)
C104—C103—H103119.5C371—C372—C373120.8 (3)
C102—C103—H103119.5C371—C372—H372119.6
C103—C104—C105119.4 (3)C373—C372—H372119.6
C103—C104—H104120.3C374—C373—C372119.2 (3)
C105—C104—H104120.3C374—C373—H373120.4
C104—C105—C106120.4 (3)C372—C373—H373120.4
C104—C105—H105119.8C375—C374—C373121.1 (3)
C106—C105—H105119.8C375—C374—Cl37119.2 (3)
C105—C106—C101119.8 (3)C373—C374—Cl37119.7 (3)
C105—C106—H106120.1C374—C375—C376119.3 (3)
C101—C106—H106120.1C374—C375—H375120.4
N111—C10A—N110124.3 (2)C376—C375—H375120.4
N111—C10A—C17A127.9 (3)C371—C376—C375121.3 (3)
N110—C10A—C17A107.7 (2)C371—C376—H376119.3
C10A—N111—C11A115.1 (2)C375—C376—H376119.3
C22—C21—C21B120.7 (3)C30A—C37A—C37115.6 (3)
C22—C21—H21119.6C30A—C37A—C38104.1 (2)
C21B—C21—H21119.6C37—C37A—C38140.3 (3)
N211—C21A—C26A123.5 (3)N39—C38—C37A109.9 (3)
N211—C21A—C21B116.2 (3)N39—C38—C381116.3 (3)
C26A—C21A—C21B120.3 (3)C37A—C38—C381133.8 (3)
C21—C21B—C24A120.1 (3)C382—C381—C384108.1 (3)
C21—C21B—C21A120.6 (3)C382—C381—C38110.2 (2)
C24A—C21B—C21A119.2 (3)C384—C381—C38109.3 (2)
C21—C22—C23119.6 (3)C382—C381—C383109.7 (3)
C21—C22—H22120.2C384—C381—C383108.7 (3)
C23—C22—H22120.2C38—C381—C383110.9 (3)
C24—C23—C22119.8 (3)C381—C382—H38A109.5
C24—C23—H23120.1C381—C382—H38B109.5
C22—C23—H23120.1H38A—C382—H38B109.5
C23—C24—C24A121.6 (3)C381—C382—H38C109.5
C23—C24—H24119.2H38A—C382—H38C109.5
C24A—C24—H24119.2H38B—C382—H38C109.5
C24—C24A—C21B118.2 (3)C381—C383—H38D109.5
C24—C24A—C25122.6 (3)C381—C383—H38E109.5
C21B—C24A—C25119.2 (3)H38D—C383—H38E109.5
C26—C25—C24A114.0 (3)C381—C383—H38F109.5
C26—C25—H25A108.7H38D—C383—H38F109.5
C24A—C25—H25A108.7H38E—C383—H38F109.5
C26—C25—H25B108.7C381—C384—H38G109.5
C24A—C25—H25B108.7C381—C384—H38H109.5
H25A—C25—H25B107.6H38G—C384—H38H109.5
C25—C26—C26A113.6 (3)C381—C384—H38I109.5
C25—C26—H26A108.9H38G—C384—H38I109.5
C26A—C26—H26A108.9H38H—C384—H38I109.5
C25—C26—H26B108.9C38—N39—N310107.8 (2)
C26A—C26—H26B108.9N39—N310—C30A110.6 (2)
H26A—C26—H26B107.7N39—N310—C301118.7 (2)
C27—C26A—C21A120.0 (3)C30A—N310—C301130.7 (2)
C27—C26A—C26122.6 (3)C302—C301—C306120.3 (3)
C21A—C26A—C26117.3 (3)C302—C301—N310120.6 (3)
C26A—C27—C27A117.8 (3)C306—C301—N310119.1 (3)
C26A—C27—C271118.0 (3)C301—C302—C303119.1 (3)
C27A—C27—C271124.0 (3)C301—C302—H302120.5
C276—C271—C272118.2 (3)C303—C302—H302120.5
C276—C271—C27122.8 (3)C304—C303—C302120.9 (3)
C272—C271—C27118.9 (3)C304—C303—H303119.6
C273—C272—C271121.2 (3)C302—C303—H303119.6
C273—C272—H272119.4C305—C304—C303119.4 (3)
C271—C272—H272119.4C305—C304—H304120.3
C274—C273—C272119.2 (3)C303—C304—H304120.3
C274—C273—H273120.4C304—C305—C306120.6 (3)
C272—C273—H273120.4C304—C305—H305119.7
C273—C274—C275121.2 (3)C306—C305—H305119.7
C273—C274—Cl27119.1 (2)C305—C306—C301119.7 (3)
C275—C274—Cl27119.7 (2)C305—C306—H306120.1
C274—C275—C276118.9 (3)C301—C306—H306120.1
C274—C275—H275120.6N311—C30A—N310124.0 (3)
C276—C275—H275120.6N311—C30A—C37A128.4 (3)
C271—C276—C275121.4 (3)N310—C30A—C37A107.6 (3)
C271—C276—H276119.3C30A—N311—C31A114.5 (2)
C275—C276—H276119.3
C12—C11—C11B—C14A0.9 (5)C26A—C27—C27A—C20A4.7 (4)
C12—C11—C11B—C11A179.7 (3)C271—C27—C27A—C20A170.6 (3)
N111—C11A—C11B—C14A166.2 (3)C26A—C27—C27A—C28179.7 (3)
C16A—C11A—C11B—C14A12.5 (4)C271—C27—C27A—C285.1 (6)
N111—C11A—C11B—C1112.5 (4)C20A—C27A—C28—N291.1 (3)
C16A—C11A—C11B—C11168.8 (3)C27—C27A—C28—N29174.9 (4)
C11B—C11—C12—C130.1 (5)C20A—C27A—C28—C281176.6 (3)
C11—C12—C13—C140.5 (5)C27—C27A—C28—C2817.4 (6)
C12—C13—C14—C14A0.3 (5)N29—C28—C281—C283122.4 (3)
C13—C14—C14A—C11B0.5 (5)C27A—C28—C281—C28360.0 (4)
C13—C14—C14A—C15176.6 (3)N29—C28—C281—C2843.5 (4)
C11—C11B—C14A—C141.2 (5)C27A—C28—C281—C284178.9 (3)
C11A—C11B—C14A—C14179.9 (3)N29—C28—C281—C282114.6 (3)
C11—C11B—C14A—C15176.1 (3)C27A—C28—C281—C28263.0 (4)
C11A—C11B—C14A—C152.7 (5)C27A—C28—N29—N2100.2 (3)
C14—C14A—C15—C16150.1 (3)C281—C28—N29—N210177.9 (2)
C11B—C14A—C15—C1632.7 (5)C28—N29—N210—C20A0.8 (3)
C14A—C15—C16—C16A47.7 (4)C28—N29—N210—C201175.6 (2)
N111—C11A—C16A—C170.3 (4)C20A—N210—C201—C20226.7 (5)
C11B—C11A—C16A—C17178.3 (3)N29—N210—C201—C202149.0 (3)
N111—C11A—C16A—C16177.9 (3)C20A—N210—C201—C206155.6 (3)
C11B—C11A—C16A—C163.5 (4)N29—N210—C201—C20628.7 (4)
C15—C16—C16A—C17148.2 (3)C206—C201—C202—C2030.3 (5)
C15—C16—C16A—C11A33.6 (4)N210—C201—C202—C203178.0 (3)
C11A—C16A—C17—C17A0.6 (4)C201—C202—C203—C2041.4 (5)
C16—C16A—C17—C17A178.7 (3)C202—C203—C204—C2051.1 (5)
C11A—C16A—C17—C171179.5 (3)C203—C204—C205—C2060.3 (6)
C16—C16A—C17—C1712.3 (4)C204—C205—C206—C2011.4 (5)
C16A—C17—C171—C17287.8 (4)C202—C201—C206—C2051.1 (5)
C17A—C17—C171—C17293.3 (4)N210—C201—C206—C205176.7 (3)
C16A—C17—C171—C17689.1 (4)N29—N210—C20A—N211178.5 (3)
C17A—C17—C171—C17689.8 (4)C201—N210—C20A—N2115.6 (5)
C176—C171—C172—C1731.7 (5)N29—N210—C20A—C27A1.5 (3)
C17—C171—C172—C173178.8 (3)C201—N210—C20A—C27A174.4 (3)
C171—C172—C173—C1740.1 (5)C27—C27A—C20A—N2114.3 (5)
C172—C173—C174—C1752.0 (5)C28—C27A—C20A—N211178.5 (3)
C172—C173—C174—Cl17178.6 (3)C27—C27A—C20A—N210175.6 (3)
C173—C174—C175—C1762.4 (5)C28—C27A—C20A—N2101.6 (3)
Cl17—C174—C175—C176178.1 (2)N210—C20A—N211—C21A179.5 (3)
C172—C171—C176—C1751.3 (5)C27A—C20A—N211—C21A0.5 (4)
C17—C171—C176—C175178.3 (3)C26A—C21A—N211—C20A2.9 (4)
C174—C175—C176—C1710.8 (5)C21B—C21A—N211—C20A179.3 (2)
C16A—C17—C17A—C10A0.8 (4)C32—C31—C31B—C34A1.3 (5)
C171—C17—C17A—C10A179.6 (3)C32—C31—C31B—C31A180.0 (3)
C16A—C17—C17A—C18178.7 (3)N311—C31A—C31B—C3112.0 (4)
C171—C17—C17A—C180.2 (6)C36A—C31A—C31B—C31168.0 (3)
C17—C17A—C18—N19178.9 (3)N311—C31A—C31B—C34A166.7 (3)
C10A—C17A—C18—N190.5 (3)C36A—C31A—C31B—C34A13.3 (4)
C17—C17A—C18—C1810.7 (6)C31B—C31—C32—C330.4 (5)
C10A—C17A—C18—C181178.8 (3)C31—C32—C33—C340.2 (5)
N19—C18—C181—C183121.7 (3)C32—C33—C34—C34A0.0 (5)
C17A—C18—C181—C18360.1 (4)C33—C34—C34A—C31B0.9 (5)
N19—C18—C181—C1841.9 (4)C33—C34—C34A—C35177.5 (3)
C17A—C18—C181—C184180.0 (3)C31—C31B—C34A—C341.5 (5)
N19—C18—C181—C182115.6 (3)C31A—C31B—C34A—C34179.8 (3)
C17A—C18—C181—C18262.6 (4)C31—C31B—C34A—C35176.9 (3)
C17A—C18—N19—N1100.3 (3)C31A—C31B—C34A—C351.8 (4)
C181—C18—N19—N110178.8 (2)C34—C34A—C35—C36150.1 (3)
C18—N19—N110—C10A0.1 (3)C31B—C34A—C35—C3631.5 (4)
C18—N19—N110—C101177.8 (2)C34A—C35—C36—C36A45.7 (4)
C10A—N110—C101—C106161.0 (3)N311—C31A—C36A—C370.7 (5)
N19—N110—C101—C10621.6 (4)C31B—C31A—C36A—C37179.2 (3)
C10A—N110—C101—C10221.6 (5)N311—C31A—C36A—C36177.8 (3)
N19—N110—C101—C102155.9 (3)C31B—C31A—C36A—C362.2 (4)
C106—C101—C102—C1030.5 (5)C35—C36—C36A—C37150.0 (3)
N110—C101—C102—C103177.9 (3)C35—C36—C36A—C31A31.5 (4)
C101—C102—C103—C1041.4 (5)C31A—C36A—C37—C37A1.3 (4)
C102—C103—C104—C1051.5 (5)C36—C36A—C37—C37A179.8 (3)
C103—C104—C105—C1060.6 (5)C31A—C36A—C37—C371178.0 (3)
C104—C105—C106—C1010.3 (5)C36—C36A—C37—C3710.5 (4)
C102—C101—C106—C1050.4 (5)C36A—C37—C371—C37694.4 (4)
N110—C101—C106—C105177.1 (3)C37A—C37—C371—C37686.3 (4)
N19—N110—C10A—N111179.4 (3)C36A—C37—C371—C37282.7 (4)
C101—N110—C10A—N1111.8 (5)C37A—C37—C371—C37296.6 (4)
N19—N110—C10A—C17A0.4 (3)C376—C371—C372—C3732.1 (5)
C101—N110—C10A—C17A177.2 (3)C37—C371—C372—C373179.2 (3)
C17—C17A—C10A—N1110.1 (4)C371—C372—C373—C3741.1 (5)
C18—C17A—C10A—N111179.5 (3)C372—C373—C374—C3750.7 (5)
C17—C17A—C10A—N110179.0 (2)C372—C373—C374—Cl37179.8 (3)
C18—C17A—C10A—N1100.6 (3)C373—C374—C375—C3761.3 (5)
N110—C10A—N111—C11A178.0 (3)Cl37—C374—C375—C376179.6 (2)
C17A—C10A—N111—C11A0.8 (4)C372—C371—C376—C3751.4 (4)
C16A—C11A—N111—C10A1.0 (4)C37—C371—C376—C375178.5 (3)
C11B—C11A—N111—C10A177.7 (2)C374—C375—C376—C3710.3 (4)
C22—C21—C21B—C24A0.9 (5)C36A—C37—C37A—C30A1.7 (4)
C22—C21—C21B—C21A178.9 (3)C371—C37—C37A—C30A177.6 (3)
N211—C21A—C21B—C218.5 (4)C36A—C37—C37A—C38176.5 (3)
C26A—C21A—C21B—C21169.4 (3)C371—C37—C37A—C384.2 (6)
N211—C21A—C21B—C24A169.5 (3)C30A—C37A—C38—N390.7 (3)
C26A—C21A—C21B—C24A12.7 (4)C37—C37A—C38—N39179.0 (4)
C21B—C21—C22—C230.6 (5)C30A—C37A—C38—C381175.9 (3)
C21—C22—C23—C240.9 (5)C37—C37A—C38—C3812.4 (6)
C22—C23—C24—C24A0.3 (5)N39—C38—C381—C382108.8 (3)
C23—C24—C24A—C21B1.8 (5)C37A—C38—C381—C38267.6 (4)
C23—C24—C24A—C25176.1 (3)N39—C38—C381—C3849.8 (4)
C21—C21B—C24A—C242.1 (5)C37A—C38—C381—C384173.8 (3)
C21A—C21B—C24A—C24179.9 (3)N39—C38—C381—C383129.6 (3)
C21—C21B—C24A—C25175.9 (3)C37A—C38—C381—C38354.0 (4)
C21A—C21B—C24A—C252.1 (4)C37A—C38—N39—N3100.2 (3)
C24—C24A—C25—C26149.8 (3)C381—C38—N39—N310177.0 (2)
C21B—C24A—C25—C2632.4 (5)C38—N39—N310—C30A0.4 (3)
C24A—C25—C26—C26A47.6 (4)C38—N39—N310—C301179.3 (3)
N211—C21A—C26A—C272.3 (5)N39—N310—C301—C302152.0 (3)
C21B—C21A—C26A—C27179.9 (3)C30A—N310—C301—C30228.4 (5)
N211—C21A—C26A—C26173.8 (3)N39—N310—C301—C30625.9 (4)
C21B—C21A—C26A—C263.9 (4)C30A—N310—C301—C306153.7 (3)
C25—C26—C26A—C27150.3 (3)C306—C301—C302—C3030.9 (5)
C25—C26—C26A—C21A33.8 (4)N310—C301—C302—C303177.0 (3)
C21A—C26A—C27—C27A1.9 (4)C301—C302—C303—C3040.7 (5)
C26—C26A—C27—C27A177.7 (3)C302—C303—C304—C3051.2 (6)
C21A—C26A—C27—C271173.7 (3)C303—C304—C305—C3060.1 (5)
C26—C26A—C27—C2712.1 (5)C304—C305—C306—C3011.5 (5)
C26A—C27—C271—C27689.9 (4)C302—C301—C306—C3052.0 (5)
C27A—C27—C271—C27694.9 (4)N310—C301—C306—C305175.9 (3)
C26A—C27—C271—C27285.4 (4)N39—N310—C30A—N311178.9 (3)
C27A—C27—C271—C27289.8 (4)C301—N310—C30A—N3111.5 (5)
C276—C271—C272—C2731.2 (4)N39—N310—C30A—C37A0.8 (3)
C27—C271—C272—C273176.8 (3)C301—N310—C30A—C37A178.8 (3)
C271—C272—C273—C2741.3 (4)C37—C37A—C30A—N3110.0 (5)
C272—C273—C274—C2750.7 (5)C38—C37A—C30A—N311178.8 (3)
C272—C273—C274—Cl27178.8 (2)C37—C37A—C30A—N310179.7 (3)
C273—C274—C275—C2760.2 (5)C38—C37A—C30A—N3100.9 (3)
Cl27—C274—C275—C276179.3 (2)N310—C30A—N311—C31A177.7 (3)
C272—C271—C276—C2750.7 (5)C37A—C30A—N311—C31A1.9 (4)
C27—C271—C276—C275176.1 (3)C36A—C31A—N311—C30A2.3 (4)
C274—C275—C276—C2710.2 (5)C31B—C31A—N311—C30A177.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C173—H173···Cg2i0.952.623.532 (4)162
C175—H175···Cg1ii0.952.643.513 (4)153
C273—H273···Cg4iii0.952.853.687 (3)147
C375—H375···Cg3iv0.952.693.698 (4)161
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC30H26ClN3
Mr463.99
Crystal system, space groupTriclinic, 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)
V3)3624.7 (10)
Z6
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.57 × 0.32 × 0.19
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.904, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
87246, 16583, 8207
Rint0.074
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.211, 1.05
No. of reflections16583
No. of parameters928
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.50

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005) and WinGX (Farrugia, 1999), OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C173—H173···Cg2i0.952.623.532 (4)162
C175—H175···Cg1ii0.952.643.513 (4)153
C273—H273···Cg4iii0.952.853.687 (3)147
C375—H375···Cg3iv0.952.693.698 (4)161
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x+1, y, z.
Ring-puckering parameters and selected torsion angles (°) for (I)–(III) top
Parameter(I), x = 1(I), x = 2(I), x = 3(II)(III)
θ116.6 (4)116.1 (4)115.1 (5)116.6 (5)115.4 (2)
ϕ31.1 (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.
 

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