Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113000954/fn3124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113000954/fn3124Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113000954/fn3124Isup3.cml |
CCDC reference: 925773
For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Etter et al. (1990); European (2011); Flack (1983); Hooft et al. (2008); Kwong et al. (2011); Lavanchy (1999); Revill et al. (2007); Spek (2009); Yip et al. (2004); Znabet et al. (2010).
Telaprevir was obtained from Sandoz, Kundl (Austria). The compound (100 mg) was dissolved in boiling acetonitrile (5 ml). The resulting clear solution was allowed to cool to room temperature. Plate-shaped single crystals of (I) were obtained after 24 h.
All H atoms, except those in the disordered fragments, were identified in a difference map. Methyl H atoms were idealized and included as rigid groups allowed to rotate but not tip (C—H = 0.98 Å) and H atoms bonded to tertiary CH (C—H = 0.99 Å), secondary CH2 (C—H = 0.99 Å) and aromatic C atoms (C—H = 0.95 Å) were positioned geometrically, except for the H atoms on atoms C47 and C47', which were refined with restrained distances [C—H = 1.00 (2) Å]. H atoms of NH groups were refined with restrained distances [N—H = 0.88 (2) Å]. The displacement parameters of the methyl H atoms were set at Uiso(H) = 1.5Ueq(C). For all other H atoms they were set at Uiso(H) = 1.2Ueq(C,N). C atoms in the disordered C18—C19—C20—C21/C18—C19''—C20''—C21 chain were refined with restrained C—C bond lengths and also with restrained second-neighbour C···C distances [1.520 (5) and 2.52 (2) Å]. Cyclopenta[c]pyrrolidine C-atom positions affected by disorder were refined with restrained C—C distances [1.500 (8) Å] and the three cyclopropyl C—C distances were also restrained [1.500 (3) Å]. The relative occupancies of the disorder components were determined by refinement but were set at constant values in the final refinement cycles. All C atoms in the minor disorder components were refined with isotropic displacement parameters.
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Bruker, 1998) and Mercury (Bruno et al., 2002); software used to prepare material for publication: publCIF (Westrip, 2010).
C36H53N7O6 | F(000) = 2928 |
Mr = 679.85 | Dx = 1.212 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 16130 reflections |
a = 10.4235 (2) Å | θ = 3.3–67.2° |
b = 19.1651 (2) Å | µ = 0.68 mm−1 |
c = 37.2907 (4) Å | T = 173 K |
V = 7449.47 (18) Å3 | Block, colourless |
Z = 8 | 0.10 × 0.10 × 0.10 mm |
Agilent Xcalibur Ruby Gemini ultra diffractometer | 13136 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray Source | 12517 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.025 |
Detector resolution: 10.3575 pixels mm-1 | θmax = 67.3°, θmin = 3.3° |
ω scans | h = −12→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −18→22 |
Tmin = 0.861, Tmax = 1.000 | l = −44→43 |
28223 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0608P)2 + 2.7241P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.044 |
13136 reflections | Δρmax = 0.54 e Å−3 |
945 parameters | Δρmin = −0.49 e Å−3 |
41 restraints | Absolute structure: Flack (1983), 5813 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (15) |
C36H53N7O6 | V = 7449.47 (18) Å3 |
Mr = 679.85 | Z = 8 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 10.4235 (2) Å | µ = 0.68 mm−1 |
b = 19.1651 (2) Å | T = 173 K |
c = 37.2907 (4) Å | 0.10 × 0.10 × 0.10 mm |
Agilent Xcalibur Ruby Gemini ultra diffractometer | 13136 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 12517 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 1.000 | Rint = 0.025 |
28223 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | Δρmax = 0.54 e Å−3 |
S = 1.03 | Δρmin = −0.49 e Å−3 |
13136 reflections | Absolute structure: Flack (1983), 5813 Friedel pairs |
945 parameters | Absolute structure parameter: −0.01 (15) |
41 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.0728 (2) | 0.53650 (10) | 0.30074 (5) | 0.0390 (4) | |
C2 | −0.0004 (3) | 0.60079 (13) | 0.29304 (6) | 0.0464 (6) | |
H2A | 0.0586 | 0.6403 | 0.2885 | 0.056* | |
H2B | −0.0567 | 0.6129 | 0.3135 | 0.056* | |
C3 | −0.0812 (4) | 0.58467 (17) | 0.25927 (9) | 0.0798 (11) | |
H3A | −0.0498 | 0.6144 | 0.2391 | 0.096* | 0.70 |
H3C | −0.0758 | 0.6187 | 0.2390 | 0.096* | 0.30 |
C4 | −0.0516 (3) | 0.50794 (16) | 0.25055 (7) | 0.0642 (8) | |
H4A | −0.0425 | 0.5018 | 0.2240 | 0.077* | |
C5 | 0.0751 (3) | 0.49116 (13) | 0.26902 (6) | 0.0498 (6) | |
H5A | 0.0811 | 0.4407 | 0.2757 | 0.060* | |
C6 | −0.2212 (5) | 0.5888 (3) | 0.26053 (17) | 0.095 (2) | 0.70 |
H6A | −0.2591 | 0.5885 | 0.2362 | 0.114* | 0.70 |
H6B | −0.2506 | 0.6309 | 0.2736 | 0.114* | 0.70 |
C7 | −0.2524 (5) | 0.5227 (3) | 0.28089 (15) | 0.0801 (16) | 0.70 |
H7A | −0.3441 | 0.5104 | 0.2782 | 0.096* | 0.70 |
H7B | −0.2329 | 0.5282 | 0.3067 | 0.096* | 0.70 |
C6" | −0.2154 (9) | 0.5751 (8) | 0.2774 (3) | 0.103 (6)* | 0.30 |
H6"1 | −0.2037 | 0.5684 | 0.3035 | 0.124* | 0.30 |
H6"2 | −0.2670 | 0.6179 | 0.2737 | 0.124* | 0.30 |
C7" | −0.2863 (9) | 0.5136 (5) | 0.2621 (4) | 0.070 (3)* | 0.30 |
H7"1 | −0.3173 | 0.5213 | 0.2373 | 0.084* | 0.30 |
H7"2 | −0.3571 | 0.4971 | 0.2777 | 0.084* | 0.30 |
C8 | −0.1668 (3) | 0.46703 (17) | 0.26398 (9) | 0.0683 (8) | |
H8A | −0.1407 | 0.4317 | 0.2819 | 0.082* | 0.70 |
H8B | −0.2113 | 0.4433 | 0.2439 | 0.082* | 0.70 |
H8E | −0.1520 | 0.4518 | 0.2890 | 0.082* | 0.30 |
H8F | −0.1794 | 0.4250 | 0.2490 | 0.082* | 0.30 |
C9 | 0.1424 (2) | 0.52069 (11) | 0.32993 (6) | 0.0373 (5) | |
O10 | 0.19418 (19) | 0.46308 (8) | 0.33352 (5) | 0.0488 (4) | |
C11 | 0.1884 (4) | 0.51414 (15) | 0.24649 (7) | 0.0634 (9) | |
O12 | 0.1943 (4) | 0.57364 (12) | 0.23480 (10) | 0.1319 (16) | |
C13 | 0.1568 (2) | 0.57630 (11) | 0.35896 (6) | 0.0343 (4) | |
H13A | 0.0956 | 0.6151 | 0.3535 | 0.041* | |
N14 | 0.11817 (17) | 0.54416 (10) | 0.39263 (5) | 0.0325 (4) | |
H14A | 0.147 (2) | 0.5030 (10) | 0.3965 (7) | 0.039* | |
C15 | 0.0243 (2) | 0.57084 (11) | 0.41327 (6) | 0.0358 (5) | |
O16 | −0.01760 (18) | 0.63017 (9) | 0.41015 (5) | 0.0491 (4) | |
N17 | 0.2797 (2) | 0.46714 (13) | 0.23969 (6) | 0.0488 (5) | |
H17A | 0.263 (3) | 0.4230 (10) | 0.2425 (9) | 0.059* | |
C18 | 0.3843 (2) | 0.49098 (17) | 0.21745 (8) | 0.0601 (8) | |
H18A | 0.4154 | 0.5349 | 0.2291 | 0.072* | 0.75 |
H18C | 0.4475 | 0.5231 | 0.2290 | 0.072* | 0.25 |
C19 | 0.4950 (3) | 0.44265 (17) | 0.21843 (8) | 0.0486 (8) | 0.75 |
H19A | 0.5177 | 0.4324 | 0.2437 | 0.058* | 0.75 |
H19B | 0.5700 | 0.4651 | 0.2069 | 0.058* | 0.75 |
C20 | 0.4640 (3) | 0.3755 (2) | 0.19920 (10) | 0.0600 (11) | 0.75 |
H20A | 0.4458 | 0.3861 | 0.1737 | 0.072* | 0.75 |
H20B | 0.3853 | 0.3553 | 0.2098 | 0.072* | 0.75 |
C19" | 0.440 (2) | 0.4259 (7) | 0.1987 (3) | 0.113 (7)* | 0.25 |
H19E | 0.3690 | 0.4013 | 0.1865 | 0.136* | 0.25 |
H19F | 0.5005 | 0.4419 | 0.1799 | 0.136* | 0.25 |
C20" | 0.5100 (12) | 0.3734 (5) | 0.2223 (3) | 0.060 (3)* | 0.25 |
H20E | 0.5737 | 0.3983 | 0.2373 | 0.072* | 0.25 |
H20F | 0.4474 | 0.3509 | 0.2386 | 0.072* | 0.25 |
C21 | 0.5761 (4) | 0.3190 (2) | 0.20114 (11) | 0.0895 (12) | |
H21A | 0.6511 | 0.3362 | 0.1879 | 0.134* | |
H21B | 0.5466 | 0.2752 | 0.1904 | 0.134* | |
H21C | 0.5996 | 0.3110 | 0.2263 | 0.134* | |
C22 | 0.2951 (2) | 0.60730 (14) | 0.36020 (8) | 0.0508 (6) | |
C23 | 0.3922 (3) | 0.55447 (16) | 0.37503 (10) | 0.0615 (8) | |
H23A | 0.4775 | 0.5759 | 0.3759 | 0.092* | |
H23B | 0.3946 | 0.5134 | 0.3594 | 0.092* | |
H23C | 0.3664 | 0.5404 | 0.3992 | 0.092* | |
C24 | −0.0348 (2) | 0.51973 (12) | 0.43960 (6) | 0.0390 (5) | |
H24A | 0.0249 | 0.4795 | 0.4431 | 0.047* | |
N25 | −0.0553 (2) | 0.55455 (11) | 0.47392 (5) | 0.0422 (5) | |
H25A | −0.102 (3) | 0.5912 (12) | 0.4741 (8) | 0.051* | |
C26 | 0.0054 (2) | 0.53653 (12) | 0.50375 (6) | 0.0371 (5) | |
O27 | 0.0840 (2) | 0.48900 (11) | 0.50562 (5) | 0.0617 (5) | |
C28 | 0.3332 (2) | 0.51327 (12) | 0.18145 (6) | 0.0356 (5) | |
O29 | 0.2469 (2) | 0.48357 (11) | 0.16733 (5) | 0.0610 (6) | |
C30 | 0.2901 (3) | 0.67083 (16) | 0.38481 (12) | 0.0758 (10) | |
H30A | 0.2625 | 0.6564 | 0.4088 | 0.114* | |
H30B | 0.2291 | 0.7049 | 0.3752 | 0.114* | |
H30C | 0.3755 | 0.6920 | 0.3863 | 0.114* | |
C31 | 0.3347 (3) | 0.6292 (2) | 0.32224 (10) | 0.0768 (10) | |
H31A | 0.4189 | 0.6518 | 0.3231 | 0.115* | |
H31B | 0.2712 | 0.6619 | 0.3126 | 0.115* | |
H31C | 0.3391 | 0.5879 | 0.3068 | 0.115* | |
C32 | −0.1638 (3) | 0.49272 (15) | 0.42396 (6) | 0.0476 (6) | |
H32A | −0.2262 | 0.5324 | 0.4240 | 0.057* | |
C33 | −0.1492 (3) | 0.46724 (16) | 0.38500 (7) | 0.0516 (6) | |
H33A | −0.1202 | 0.5065 | 0.3698 | 0.062* | |
H33B | −0.0830 | 0.4303 | 0.3840 | 0.062* | |
C34 | −0.2755 (3) | 0.4387 (2) | 0.37041 (9) | 0.0770 (10) | |
H34A | −0.3393 | 0.4769 | 0.3691 | 0.092* | |
H34B | −0.2619 | 0.4206 | 0.3458 | 0.092* | |
C35 | −0.3268 (4) | 0.3812 (3) | 0.39390 (10) | 0.1020 (16) | |
H35A | −0.2660 | 0.3415 | 0.3938 | 0.122* | |
H35B | −0.4096 | 0.3645 | 0.3841 | 0.122* | |
C36 | −0.3460 (4) | 0.4064 (3) | 0.43192 (10) | 0.0934 (14) | |
H36A | −0.3774 | 0.3675 | 0.4470 | 0.112* | |
H36B | −0.4115 | 0.4438 | 0.4323 | 0.112* | |
C37 | −0.2189 (3) | 0.43455 (17) | 0.44743 (8) | 0.0616 (8) | |
H37A | −0.2340 | 0.4527 | 0.4719 | 0.074* | |
H37B | −0.1560 | 0.3960 | 0.4491 | 0.074* | |
C38 | −0.0283 (2) | 0.57804 (12) | 0.53665 (6) | 0.0356 (5) | |
N39 | −0.1136 (2) | 0.62872 (11) | 0.53344 (5) | 0.0434 (5) | |
C40 | −0.1449 (3) | 0.66146 (14) | 0.56383 (7) | 0.0496 (6) | |
H40A | −0.2057 | 0.6983 | 0.5629 | 0.060* | |
C41 | −0.0923 (2) | 0.64377 (14) | 0.59650 (7) | 0.0455 (6) | |
H41A | −0.1206 | 0.6676 | 0.6174 | 0.055* | |
N42 | −0.0042 (3) | 0.59495 (14) | 0.59967 (6) | 0.0612 (6) | |
C43 | 0.0271 (3) | 0.56248 (17) | 0.56928 (7) | 0.0592 (7) | |
H43A | 0.0906 | 0.5270 | 0.5701 | 0.071* | |
C44 | 0.3997 (2) | 0.57478 (12) | 0.16325 (6) | 0.0355 (5) | |
O45 | 0.48539 (17) | 0.60658 (10) | 0.17897 (5) | 0.0517 (4) | |
N46 | 0.35535 (19) | 0.58837 (10) | 0.13061 (5) | 0.0367 (4) | |
H46A | 0.289 (2) | 0.5642 (13) | 0.1228 (7) | 0.044* | |
C47 | 0.4075 (2) | 0.64312 (12) | 0.10902 (5) | 0.0398 (5) | |
H47 | 0.486 (2) | 0.6652 (14) | 0.1185 (7) | 0.048* | |
C48 | 0.3206 (3) | 0.68761 (17) | 0.08706 (10) | 0.0833 (12) | |
H48A | 0.3418 | 0.7378 | 0.0849 | 0.100* | |
H48B | 0.2277 | 0.6769 | 0.0875 | 0.100* | |
C49 | 0.4078 (3) | 0.63640 (15) | 0.06921 (6) | 0.0630 (8) | |
H49A | 0.3688 | 0.5940 | 0.0587 | 0.076* | |
H49B | 0.4828 | 0.6549 | 0.0560 | 0.076* | |
N1' | 0.48615 (19) | 0.51474 (10) | 0.54763 (5) | 0.0380 (4) | |
C2' | 0.6024 (3) | 0.54288 (17) | 0.53076 (7) | 0.0564 (7) | |
H2C | 0.6623 | 0.5049 | 0.5241 | 0.068* | |
H2D | 0.6469 | 0.5757 | 0.5471 | 0.068* | |
C3' | 0.5531 (3) | 0.58036 (15) | 0.49757 (8) | 0.0620 (8) | |
H3B | 0.6082 | 0.5716 | 0.4761 | 0.074* | 0.70 |
H3D | 0.6020 | 0.5590 | 0.4773 | 0.074* | 0.30 |
C4' | 0.4129 (3) | 0.55572 (14) | 0.49185 (7) | 0.0541 (7) | |
H4B | 0.4015 | 0.5357 | 0.4673 | 0.065* | |
C5' | 0.3889 (2) | 0.49945 (12) | 0.52087 (6) | 0.0387 (5) | |
H5B | 0.3011 | 0.5049 | 0.5314 | 0.046* | |
C6' | 0.5425 (5) | 0.6599 (2) | 0.50670 (15) | 0.0716 (14) | 0.70 |
H6C | 0.5337 | 0.6676 | 0.5328 | 0.086* | 0.70 |
H6D | 0.6175 | 0.6862 | 0.4977 | 0.086* | 0.70 |
C7' | 0.4220 (5) | 0.6793 (2) | 0.48695 (14) | 0.0737 (15) | 0.70 |
H7C | 0.3887 | 0.7250 | 0.4951 | 0.088* | 0.70 |
H7D | 0.4369 | 0.6812 | 0.4607 | 0.088* | 0.70 |
C7X | 0.4223 (10) | 0.6791 (6) | 0.5078 (4) | 0.074 (3)* | 0.30 |
H7X1 | 0.3923 | 0.7257 | 0.4999 | 0.088* | 0.30 |
H7X2 | 0.4377 | 0.6794 | 0.5340 | 0.088* | 0.30 |
C6X | 0.5372 (12) | 0.6549 (4) | 0.4872 (4) | 0.072 (3)* | 0.30 |
H6X1 | 0.5225 | 0.6593 | 0.4610 | 0.086* | 0.30 |
H6X2 | 0.6141 | 0.6824 | 0.4937 | 0.086* | 0.30 |
C8' | 0.3315 (4) | 0.62128 (15) | 0.49655 (10) | 0.0726 (9) | |
H8C | 0.2564 | 0.6207 | 0.4803 | 0.087* | 0.70 |
H8D | 0.3011 | 0.6259 | 0.5216 | 0.087* | 0.70 |
H8G | 0.2884 | 0.6335 | 0.4737 | 0.087* | 0.30 |
H8H | 0.2651 | 0.6137 | 0.5151 | 0.087* | 0.30 |
C9' | 0.4661 (2) | 0.49805 (11) | 0.58208 (5) | 0.0321 (4) | |
O10' | 0.36367 (15) | 0.47171 (9) | 0.59162 (4) | 0.0411 (4) | |
C11' | 0.4068 (2) | 0.42538 (12) | 0.50599 (6) | 0.0385 (5) | |
O12' | 0.50772 (18) | 0.39389 (10) | 0.50909 (5) | 0.0533 (5) | |
C13' | 0.5699 (2) | 0.51505 (11) | 0.60970 (6) | 0.0333 (4) | |
H13B | 0.6346 | 0.5461 | 0.5980 | 0.040* | |
N14' | 0.50505 (17) | 0.55509 (9) | 0.63766 (5) | 0.0326 (4) | |
H14B | 0.4269 (18) | 0.5423 (13) | 0.6439 (7) | 0.039* | |
C15' | 0.5415 (2) | 0.62015 (11) | 0.64667 (6) | 0.0334 (4) | |
O16' | 0.64389 (16) | 0.64679 (9) | 0.63770 (5) | 0.0473 (4) | |
N17' | 0.3033 (2) | 0.40082 (10) | 0.48863 (5) | 0.0394 (4) | |
H17B | 0.234 (2) | 0.4248 (14) | 0.4888 (8) | 0.047* | |
C18' | 0.3089 (2) | 0.33856 (11) | 0.46639 (6) | 0.0361 (5) | |
H18B | 0.3994 | 0.3212 | 0.4669 | 0.043* | |
C19' | 0.2224 (3) | 0.27912 (13) | 0.48060 (7) | 0.0493 (6) | |
H19C | 0.2438 | 0.2360 | 0.4673 | 0.059* | |
H19D | 0.2441 | 0.2710 | 0.5061 | 0.059* | |
C20' | 0.0793 (3) | 0.29072 (16) | 0.47792 (8) | 0.0579 (7) | |
H20C | 0.0369 | 0.2653 | 0.4978 | 0.069* | |
H20D | 0.0616 | 0.3411 | 0.4813 | 0.069* | |
C21' | 0.0204 (3) | 0.26767 (18) | 0.44302 (10) | 0.0702 (9) | |
H21D | 0.0566 | 0.2952 | 0.4233 | 0.105* | |
H21E | −0.0727 | 0.2747 | 0.4439 | 0.105* | |
H21F | 0.0389 | 0.2181 | 0.4391 | 0.105* | |
C22' | 0.6407 (2) | 0.44962 (12) | 0.62412 (7) | 0.0426 (5) | |
C23' | 0.7093 (3) | 0.41432 (16) | 0.59235 (8) | 0.0584 (7) | |
H23D | 0.7555 | 0.3730 | 0.6009 | 0.088* | |
H23E | 0.7704 | 0.4472 | 0.5816 | 0.088* | |
H23F | 0.6459 | 0.4004 | 0.5743 | 0.088* | |
C24' | 0.4442 (2) | 0.66178 (11) | 0.66828 (6) | 0.0324 (4) | |
H24B | 0.3757 | 0.6296 | 0.6772 | 0.039* | |
N25' | 0.51102 (19) | 0.69230 (10) | 0.69904 (5) | 0.0357 (4) | |
H25B | 0.5870 (19) | 0.7095 (14) | 0.6964 (7) | 0.043* | |
C26' | 0.4643 (2) | 0.69027 (11) | 0.73234 (6) | 0.0380 (5) | |
O27' | 0.35811 (17) | 0.66600 (9) | 0.74010 (4) | 0.0460 (4) | |
C28' | 0.2787 (2) | 0.35851 (11) | 0.42816 (6) | 0.0346 (5) | |
O29' | 0.22296 (19) | 0.41126 (9) | 0.42032 (4) | 0.0484 (4) | |
C30' | 0.5513 (3) | 0.39798 (14) | 0.64221 (9) | 0.0566 (7) | |
H30D | 0.6019 | 0.3607 | 0.6534 | 0.085* | |
H30E | 0.4933 | 0.3778 | 0.6243 | 0.085* | |
H30F | 0.5010 | 0.4221 | 0.6606 | 0.085* | |
C31' | 0.7421 (3) | 0.47455 (16) | 0.65120 (8) | 0.0550 (7) | |
H31D | 0.6996 | 0.4987 | 0.6711 | 0.082* | |
H31E | 0.8017 | 0.5066 | 0.6393 | 0.082* | |
H31F | 0.7895 | 0.4342 | 0.6605 | 0.082* | |
C32' | 0.3830 (2) | 0.71760 (11) | 0.64401 (6) | 0.0332 (4) | |
H32B | 0.4524 | 0.7496 | 0.6355 | 0.040* | |
C33' | 0.3191 (2) | 0.68447 (12) | 0.61103 (6) | 0.0407 (5) | |
H33C | 0.2533 | 0.6506 | 0.6190 | 0.049* | |
H33D | 0.3844 | 0.6588 | 0.5970 | 0.049* | |
C34' | 0.2563 (3) | 0.74002 (14) | 0.58718 (7) | 0.0510 (6) | |
H34C | 0.3236 | 0.7703 | 0.5768 | 0.061* | |
H34D | 0.2108 | 0.7168 | 0.5671 | 0.061* | |
C35' | 0.1619 (3) | 0.78455 (16) | 0.60818 (9) | 0.0585 (7) | |
H35C | 0.0886 | 0.7553 | 0.6159 | 0.070* | |
H35D | 0.1281 | 0.8219 | 0.5925 | 0.070* | |
C36' | 0.2247 (2) | 0.81735 (14) | 0.64107 (8) | 0.0492 (6) | |
H36C | 0.1596 | 0.8435 | 0.6550 | 0.059* | |
H36D | 0.2919 | 0.8506 | 0.6333 | 0.059* | |
C37' | 0.2846 (2) | 0.76105 (12) | 0.66480 (7) | 0.0401 (5) | |
H37C | 0.2163 | 0.7300 | 0.6740 | 0.048* | |
H37D | 0.3272 | 0.7833 | 0.6856 | 0.048* | |
C38' | 0.5495 (2) | 0.71968 (12) | 0.76108 (6) | 0.0407 (5) | |
N39' | 0.6574 (2) | 0.75143 (10) | 0.75107 (6) | 0.0457 (5) | |
C40' | 0.7306 (3) | 0.77649 (14) | 0.77768 (8) | 0.0577 (7) | |
H40B | 0.8076 | 0.8005 | 0.7720 | 0.069* | |
C41' | 0.6967 (4) | 0.76827 (17) | 0.81312 (9) | 0.0666 (9) | |
H41B | 0.7522 | 0.7864 | 0.8310 | 0.080* | |
N42' | 0.5897 (3) | 0.73603 (18) | 0.82344 (7) | 0.0737 (8) | |
C43' | 0.5152 (3) | 0.71171 (17) | 0.79678 (7) | 0.0597 (7) | |
H43B | 0.4373 | 0.6885 | 0.8025 | 0.072* | |
C44' | 0.3247 (2) | 0.30757 (12) | 0.39909 (6) | 0.0376 (5) | |
O45' | 0.37763 (19) | 0.25352 (9) | 0.40765 (5) | 0.0517 (4) | |
N46' | 0.3013 (2) | 0.32886 (11) | 0.36574 (5) | 0.0449 (5) | |
H46B | 0.265 (3) | 0.3693 (11) | 0.3622 (8) | 0.054* | |
C47' | 0.3331 (3) | 0.28463 (15) | 0.33622 (6) | 0.0625 (8) | |
H47' | 0.281 (3) | 0.2397 (13) | 0.3323 (9) | 0.075* | |
C48' | 0.3582 (3) | 0.31742 (19) | 0.30076 (6) | 0.0725 (10) | |
H48C | 0.3554 | 0.3690 | 0.2993 | 0.087* | |
H48D | 0.3273 | 0.2927 | 0.2791 | 0.087* | |
C49' | 0.4654 (3) | 0.2850 (2) | 0.32146 (8) | 0.0812 (11) | |
H49C | 0.5007 | 0.2402 | 0.3126 | 0.097* | |
H49D | 0.5289 | 0.3164 | 0.3328 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0544 (11) | 0.0324 (9) | 0.0301 (9) | 0.0013 (9) | 0.0064 (8) | −0.0016 (7) |
C2 | 0.0634 (16) | 0.0387 (12) | 0.0371 (12) | 0.0048 (12) | −0.0021 (12) | 0.0010 (10) |
C3 | 0.136 (3) | 0.0502 (17) | 0.0534 (18) | 0.0016 (19) | −0.036 (2) | 0.0030 (14) |
C4 | 0.107 (3) | 0.0581 (17) | 0.0277 (11) | −0.0055 (17) | −0.0083 (14) | −0.0066 (11) |
C5 | 0.0782 (18) | 0.0377 (12) | 0.0334 (12) | −0.0072 (13) | 0.0189 (12) | −0.0037 (10) |
C6 | 0.114 (5) | 0.077 (3) | 0.094 (4) | 0.040 (3) | −0.078 (4) | −0.031 (3) |
C7 | 0.068 (3) | 0.086 (4) | 0.086 (4) | 0.005 (3) | −0.031 (3) | −0.033 (3) |
C8 | 0.072 (2) | 0.0614 (18) | 0.071 (2) | −0.0002 (16) | −0.0127 (16) | −0.0153 (16) |
C9 | 0.0436 (12) | 0.0322 (11) | 0.0360 (11) | −0.0002 (10) | 0.0108 (10) | 0.0035 (9) |
O10 | 0.0681 (11) | 0.0338 (8) | 0.0445 (9) | 0.0125 (8) | 0.0098 (8) | 0.0038 (7) |
C11 | 0.101 (2) | 0.0461 (15) | 0.0426 (14) | −0.0201 (16) | 0.0316 (16) | −0.0081 (12) |
O12 | 0.211 (4) | 0.0433 (12) | 0.142 (3) | −0.0148 (17) | 0.129 (3) | −0.0059 (14) |
C13 | 0.0372 (11) | 0.0299 (10) | 0.0359 (11) | 0.0010 (9) | −0.0002 (9) | 0.0043 (9) |
N14 | 0.0367 (9) | 0.0286 (9) | 0.0322 (9) | 0.0034 (8) | −0.0026 (7) | 0.0020 (7) |
C15 | 0.0407 (11) | 0.0359 (11) | 0.0307 (10) | 0.0072 (9) | −0.0059 (9) | −0.0048 (8) |
O16 | 0.0606 (11) | 0.0391 (9) | 0.0476 (9) | 0.0162 (8) | 0.0020 (8) | −0.0013 (7) |
N17 | 0.0398 (11) | 0.0668 (14) | 0.0398 (11) | −0.0145 (11) | −0.0058 (9) | 0.0194 (10) |
C18 | 0.0348 (12) | 0.086 (2) | 0.0594 (16) | −0.0057 (13) | −0.0031 (12) | 0.0357 (15) |
C19 | 0.0403 (16) | 0.071 (2) | 0.0350 (16) | −0.0048 (16) | −0.0080 (13) | 0.0072 (15) |
C20 | 0.0313 (16) | 0.108 (3) | 0.0403 (18) | −0.0025 (19) | 0.0071 (14) | −0.024 (2) |
C21 | 0.069 (2) | 0.119 (3) | 0.081 (2) | 0.021 (2) | −0.0050 (19) | 0.002 (2) |
C22 | 0.0399 (13) | 0.0440 (13) | 0.0686 (17) | −0.0072 (11) | −0.0021 (12) | 0.0116 (12) |
C23 | 0.0391 (13) | 0.0587 (17) | 0.087 (2) | −0.0028 (12) | −0.0047 (14) | 0.0167 (15) |
C24 | 0.0464 (12) | 0.0419 (12) | 0.0287 (10) | 0.0098 (10) | 0.0031 (9) | −0.0054 (9) |
N25 | 0.0502 (11) | 0.0450 (11) | 0.0312 (9) | 0.0168 (9) | −0.0010 (8) | −0.0073 (8) |
C26 | 0.0380 (11) | 0.0418 (12) | 0.0314 (11) | 0.0026 (10) | 0.0014 (9) | −0.0044 (9) |
O27 | 0.0711 (12) | 0.0736 (13) | 0.0403 (9) | 0.0373 (11) | −0.0089 (9) | −0.0155 (9) |
C28 | 0.0354 (11) | 0.0400 (12) | 0.0315 (11) | −0.0017 (10) | 0.0042 (9) | 0.0002 (9) |
O29 | 0.0705 (12) | 0.0744 (13) | 0.0382 (9) | −0.0406 (11) | −0.0130 (9) | 0.0123 (9) |
C30 | 0.0609 (18) | 0.0494 (16) | 0.117 (3) | −0.0139 (15) | −0.0211 (19) | −0.0105 (18) |
C31 | 0.0531 (17) | 0.086 (2) | 0.091 (2) | −0.0172 (17) | 0.0094 (17) | 0.038 (2) |
C32 | 0.0483 (13) | 0.0576 (15) | 0.0368 (12) | −0.0016 (12) | 0.0082 (10) | −0.0083 (11) |
C33 | 0.0498 (14) | 0.0704 (17) | 0.0347 (12) | −0.0115 (13) | 0.0024 (11) | −0.0067 (11) |
C34 | 0.0666 (19) | 0.113 (3) | 0.0517 (17) | −0.032 (2) | −0.0003 (15) | −0.0167 (18) |
C35 | 0.093 (3) | 0.147 (4) | 0.066 (2) | −0.069 (3) | 0.019 (2) | −0.032 (2) |
C36 | 0.078 (2) | 0.131 (4) | 0.070 (2) | −0.050 (3) | 0.0282 (19) | −0.021 (2) |
C37 | 0.0679 (18) | 0.0686 (18) | 0.0482 (15) | −0.0100 (15) | 0.0203 (14) | −0.0085 (14) |
C38 | 0.0352 (11) | 0.0384 (11) | 0.0333 (11) | −0.0031 (9) | 0.0042 (9) | −0.0055 (9) |
N39 | 0.0480 (11) | 0.0427 (11) | 0.0394 (10) | 0.0027 (9) | 0.0027 (9) | −0.0079 (8) |
C40 | 0.0509 (14) | 0.0504 (14) | 0.0475 (14) | 0.0047 (12) | 0.0062 (12) | −0.0167 (11) |
C41 | 0.0449 (13) | 0.0547 (15) | 0.0369 (12) | −0.0106 (12) | 0.0117 (10) | −0.0159 (11) |
N42 | 0.0752 (16) | 0.0740 (16) | 0.0343 (11) | 0.0088 (14) | 0.0026 (11) | −0.0131 (10) |
C43 | 0.0703 (18) | 0.0688 (18) | 0.0386 (13) | 0.0233 (15) | −0.0043 (13) | −0.0096 (12) |
C44 | 0.0328 (11) | 0.0390 (11) | 0.0345 (11) | −0.0021 (9) | 0.0019 (9) | 0.0002 (9) |
O45 | 0.0441 (9) | 0.0645 (11) | 0.0465 (9) | −0.0215 (9) | −0.0086 (8) | 0.0085 (8) |
N46 | 0.0371 (10) | 0.0404 (10) | 0.0325 (9) | −0.0090 (8) | 0.0001 (8) | −0.0003 (8) |
C47 | 0.0459 (13) | 0.0373 (12) | 0.0361 (11) | −0.0092 (10) | 0.0022 (10) | 0.0030 (9) |
C48 | 0.065 (2) | 0.069 (2) | 0.116 (3) | 0.0045 (17) | 0.002 (2) | 0.051 (2) |
C49 | 0.099 (2) | 0.0548 (16) | 0.0350 (13) | −0.0247 (17) | −0.0038 (14) | 0.0080 (11) |
N1' | 0.0426 (10) | 0.0425 (10) | 0.0289 (9) | −0.0096 (9) | 0.0026 (8) | −0.0018 (7) |
C2' | 0.0591 (16) | 0.0726 (18) | 0.0375 (13) | −0.0256 (15) | 0.0078 (12) | 0.0028 (12) |
C3' | 0.079 (2) | 0.0585 (17) | 0.0484 (15) | −0.0040 (15) | 0.0216 (15) | 0.0100 (13) |
C4' | 0.088 (2) | 0.0445 (14) | 0.0301 (11) | −0.0069 (14) | −0.0047 (13) | 0.0008 (10) |
C5' | 0.0493 (13) | 0.0381 (12) | 0.0286 (10) | −0.0013 (10) | −0.0006 (10) | −0.0021 (9) |
C6' | 0.106 (4) | 0.050 (2) | 0.058 (3) | −0.028 (3) | −0.011 (3) | 0.006 (2) |
C7' | 0.123 (5) | 0.041 (2) | 0.058 (3) | −0.006 (3) | −0.006 (3) | 0.0090 (19) |
C8' | 0.085 (2) | 0.0529 (17) | 0.080 (2) | 0.0025 (17) | −0.0115 (19) | 0.0186 (16) |
C9' | 0.0375 (11) | 0.0290 (10) | 0.0299 (10) | 0.0002 (9) | 0.0026 (9) | −0.0028 (8) |
O10' | 0.0364 (8) | 0.0559 (10) | 0.0309 (7) | −0.0131 (7) | 0.0027 (6) | −0.0013 (7) |
C11' | 0.0466 (13) | 0.0406 (12) | 0.0284 (10) | −0.0022 (10) | 0.0026 (9) | −0.0017 (9) |
O12' | 0.0443 (10) | 0.0596 (11) | 0.0559 (11) | 0.0083 (9) | −0.0066 (8) | −0.0174 (9) |
C13' | 0.0330 (10) | 0.0338 (11) | 0.0331 (10) | −0.0041 (9) | 0.0023 (9) | −0.0042 (8) |
N14' | 0.0330 (9) | 0.0331 (9) | 0.0316 (9) | −0.0058 (7) | 0.0013 (7) | −0.0039 (7) |
C15' | 0.0337 (11) | 0.0330 (11) | 0.0334 (10) | −0.0025 (9) | −0.0033 (9) | −0.0011 (9) |
O16' | 0.0358 (8) | 0.0418 (9) | 0.0644 (11) | −0.0089 (7) | 0.0090 (8) | −0.0141 (8) |
N17' | 0.0418 (10) | 0.0379 (10) | 0.0387 (10) | 0.0080 (9) | −0.0045 (9) | −0.0091 (8) |
C18' | 0.0429 (12) | 0.0336 (11) | 0.0319 (11) | 0.0047 (9) | −0.0018 (9) | −0.0032 (9) |
C19' | 0.0683 (17) | 0.0376 (12) | 0.0420 (13) | −0.0008 (12) | 0.0055 (12) | 0.0013 (10) |
C20' | 0.0649 (18) | 0.0500 (15) | 0.0588 (16) | −0.0089 (14) | 0.0158 (14) | −0.0058 (13) |
C21' | 0.0665 (19) | 0.0605 (18) | 0.084 (2) | −0.0078 (16) | −0.0008 (17) | −0.0160 (16) |
C22' | 0.0403 (12) | 0.0383 (12) | 0.0492 (13) | 0.0047 (10) | −0.0046 (10) | −0.0058 (10) |
C23' | 0.0585 (16) | 0.0543 (16) | 0.0623 (17) | 0.0178 (13) | −0.0017 (14) | −0.0132 (13) |
C24' | 0.0339 (10) | 0.0320 (10) | 0.0314 (10) | −0.0054 (9) | −0.0014 (8) | −0.0048 (8) |
N25' | 0.0389 (10) | 0.0340 (9) | 0.0341 (9) | −0.0050 (8) | −0.0014 (8) | −0.0061 (7) |
C26' | 0.0467 (13) | 0.0301 (10) | 0.0371 (12) | 0.0030 (10) | −0.0044 (10) | −0.0049 (9) |
O27' | 0.0501 (10) | 0.0523 (10) | 0.0355 (8) | −0.0084 (8) | 0.0038 (7) | −0.0048 (7) |
C28' | 0.0385 (11) | 0.0293 (11) | 0.0361 (11) | 0.0033 (9) | 0.0019 (9) | −0.0028 (9) |
O29' | 0.0699 (12) | 0.0377 (9) | 0.0375 (8) | 0.0198 (8) | 0.0027 (8) | 0.0011 (7) |
C30' | 0.0590 (16) | 0.0385 (13) | 0.0723 (18) | 0.0010 (12) | −0.0090 (14) | 0.0145 (13) |
C31' | 0.0464 (14) | 0.0591 (16) | 0.0594 (16) | 0.0080 (13) | −0.0127 (13) | −0.0015 (13) |
C32' | 0.0330 (10) | 0.0329 (10) | 0.0337 (11) | −0.0039 (8) | −0.0002 (9) | −0.0044 (9) |
C33' | 0.0440 (12) | 0.0393 (12) | 0.0388 (12) | −0.0028 (10) | −0.0096 (10) | −0.0041 (10) |
C34' | 0.0574 (15) | 0.0462 (14) | 0.0494 (14) | −0.0015 (12) | −0.0196 (12) | −0.0015 (12) |
C35' | 0.0451 (15) | 0.0530 (15) | 0.0774 (19) | 0.0023 (12) | −0.0183 (14) | 0.0037 (14) |
C36' | 0.0408 (13) | 0.0424 (13) | 0.0642 (16) | 0.0058 (11) | 0.0031 (12) | −0.0010 (12) |
C37' | 0.0397 (12) | 0.0367 (12) | 0.0440 (12) | −0.0014 (10) | 0.0068 (10) | −0.0016 (10) |
C38' | 0.0505 (13) | 0.0316 (11) | 0.0400 (12) | 0.0076 (10) | −0.0085 (10) | −0.0085 (9) |
N39' | 0.0511 (12) | 0.0351 (10) | 0.0510 (12) | 0.0011 (9) | −0.0176 (10) | −0.0034 (9) |
C40' | 0.0592 (16) | 0.0453 (14) | 0.0684 (18) | 0.0032 (13) | −0.0284 (14) | −0.0079 (13) |
C41' | 0.075 (2) | 0.0677 (19) | 0.0570 (17) | 0.0165 (17) | −0.0329 (16) | −0.0256 (15) |
N42' | 0.0776 (19) | 0.098 (2) | 0.0457 (14) | 0.0152 (17) | −0.0155 (13) | −0.0275 (14) |
C43' | 0.0621 (17) | 0.0754 (19) | 0.0415 (14) | 0.0083 (15) | −0.0063 (13) | −0.0169 (13) |
C44' | 0.0422 (12) | 0.0334 (11) | 0.0374 (12) | 0.0044 (10) | 0.0027 (9) | −0.0036 (9) |
O45' | 0.0705 (12) | 0.0386 (9) | 0.0459 (9) | 0.0198 (9) | 0.0060 (9) | −0.0012 (7) |
N46' | 0.0606 (13) | 0.0398 (11) | 0.0344 (10) | 0.0143 (10) | 0.0004 (9) | −0.0046 (8) |
C47' | 0.095 (2) | 0.0535 (16) | 0.0386 (14) | 0.0098 (16) | 0.0066 (15) | −0.0136 (12) |
C48' | 0.103 (3) | 0.083 (2) | 0.0309 (13) | 0.038 (2) | −0.0002 (15) | −0.0012 (13) |
C49' | 0.070 (2) | 0.118 (3) | 0.0550 (18) | 0.030 (2) | −0.0064 (16) | −0.0243 (19) |
N1—C9 | 1.343 (3) | C48—H48A | 0.9900 |
N1—C5 | 1.468 (3) | C48—H48B | 0.9900 |
N1—C2 | 1.477 (3) | C49—H49A | 0.9900 |
C2—C3 | 1.547 (4) | C49—H49B | 0.9900 |
C2—H2A | 0.9900 | N1'—C9' | 1.340 (3) |
C2—H2B | 0.9900 | N1'—C5' | 1.452 (3) |
C3—C6 | 1.462 (6) | N1'—C2' | 1.468 (3) |
C3—C4 | 1.537 (5) | C2'—C3' | 1.521 (4) |
C3—C6" | 1.563 (8) | C2'—H2C | 0.9900 |
C3—H3A | 1.0000 | C2'—H2D | 0.9900 |
C3—H3C | 1.0000 | C3'—C6X | 1.490 (7) |
C4—C8 | 1.519 (4) | C3'—C4' | 1.551 (5) |
C4—C5 | 1.524 (5) | C3'—C6' | 1.565 (5) |
C4—H4A | 1.0000 | C3'—H3B | 1.0000 |
C5—C11 | 1.515 (4) | C3'—H3D | 1.0000 |
C5—H5A | 1.0000 | C4'—C8' | 1.526 (4) |
C6—C7 | 1.513 (6) | C4'—C5' | 1.548 (3) |
C6—H6A | 0.9900 | C4'—H4B | 1.0000 |
C6—H6B | 0.9900 | C5'—C11' | 1.536 (3) |
C7—C8 | 1.527 (5) | C5'—H5B | 1.0000 |
C7—H7A | 0.9900 | C6'—C7' | 1.503 (6) |
C7—H7B | 0.9900 | C6'—H6C | 0.9900 |
C6"—C7" | 1.504 (8) | C6'—H6D | 0.9900 |
C6"—H6"1 | 0.9900 | C7'—C8' | 1.502 (5) |
C6"—H6"2 | 0.9900 | C7'—H7C | 0.9900 |
C7"—C8 | 1.534 (7) | C7'—H7D | 0.9900 |
C7"—H7"1 | 0.9900 | C7X—C6X | 1.498 (8) |
C7"—H7"2 | 0.9900 | C7X—C8' | 1.517 (7) |
C8—H8A | 0.9900 | C7X—H7X1 | 0.9900 |
C8—H8B | 0.9900 | C7X—H7X2 | 0.9900 |
C8—H8E | 0.9900 | C6X—H6X1 | 0.9900 |
C8—H8F | 0.9900 | C6X—H6X2 | 0.9900 |
C9—O10 | 1.236 (3) | C8'—H8C | 0.9900 |
C9—C13 | 1.526 (3) | C8'—H8D | 0.9900 |
C11—O12 | 1.222 (4) | C8'—H8G | 0.9900 |
C11—N17 | 1.335 (4) | C8'—H8H | 0.9900 |
C13—N14 | 1.455 (3) | C9'—O10' | 1.234 (3) |
C13—C22 | 1.560 (3) | C9'—C13' | 1.528 (3) |
C13—H13A | 1.0000 | C11'—O12' | 1.218 (3) |
N14—C15 | 1.346 (3) | C11'—N17' | 1.343 (3) |
N14—H14A | 0.858 (17) | C13'—N14' | 1.460 (3) |
C15—O16 | 1.224 (3) | C13'—C22' | 1.551 (3) |
C15—C24 | 1.517 (3) | C13'—H13B | 1.0000 |
N17—C18 | 1.444 (3) | N14'—C15' | 1.346 (3) |
N17—H17A | 0.870 (18) | N14'—H14B | 0.883 (17) |
C18—C19 | 1.481 (3) | C15'—O16' | 1.229 (3) |
C18—C28 | 1.506 (3) | C15'—C24' | 1.522 (3) |
C18—C19" | 1.543 (5) | N17'—C18' | 1.454 (3) |
C18—H18A | 1.0000 | N17'—H17B | 0.859 (18) |
C18—H18C | 1.0000 | C18'—C28' | 1.509 (3) |
C19—C20 | 1.508 (4) | C18'—C19' | 1.547 (3) |
C19—H19A | 0.9900 | C18'—H18B | 1.0000 |
C19—H19B | 0.9900 | C19'—C20' | 1.511 (4) |
C20—C21 | 1.595 (4) | C19'—H19C | 0.9900 |
C20—H20A | 0.9900 | C19'—H19D | 0.9900 |
C20—H20B | 0.9900 | C20'—C21' | 1.505 (5) |
C19"—C20" | 1.521 (5) | C20'—H20C | 0.9900 |
C19"—H19E | 0.9900 | C20'—H20D | 0.9900 |
C19"—H19F | 0.9900 | C21'—H21D | 0.9800 |
C20"—C21 | 1.478 (5) | C21'—H21E | 0.9800 |
C20"—H20E | 0.9900 | C21'—H21F | 0.9800 |
C20"—H20F | 0.9900 | C22'—C30' | 1.518 (4) |
C21—H21A | 0.9800 | C22'—C31' | 1.538 (4) |
C21—H21B | 0.9800 | C22'—C23' | 1.540 (4) |
C21—H21C | 0.9800 | C23'—H23D | 0.9800 |
C22—C30 | 1.526 (5) | C23'—H23E | 0.9800 |
C22—C31 | 1.533 (4) | C23'—H23F | 0.9800 |
C22—C23 | 1.535 (4) | C24'—N25' | 1.464 (3) |
C23—H23A | 0.9800 | C24'—C32' | 1.540 (3) |
C23—H23B | 0.9800 | C24'—H24B | 1.0000 |
C23—H23C | 0.9800 | N25'—C26' | 1.335 (3) |
C24—N25 | 1.459 (3) | N25'—H25B | 0.863 (18) |
C24—C32 | 1.555 (4) | C26'—O27' | 1.235 (3) |
C24—H24A | 1.0000 | C26'—C38' | 1.501 (3) |
N25—C26 | 1.325 (3) | C28'—O29' | 1.202 (3) |
N25—H25A | 0.857 (18) | C28'—C44' | 1.536 (3) |
C26—O27 | 1.227 (3) | C30'—H30D | 0.9800 |
C26—C38 | 1.504 (3) | C30'—H30E | 0.9800 |
C28—O29 | 1.188 (3) | C30'—H30F | 0.9800 |
C28—C44 | 1.527 (3) | C31'—H31D | 0.9800 |
C30—H30A | 0.9800 | C31'—H31E | 0.9800 |
C30—H30B | 0.9800 | C31'—H31F | 0.9800 |
C30—H30C | 0.9800 | C32'—C37' | 1.531 (3) |
C31—H31A | 0.9800 | C32'—C33' | 1.536 (3) |
C31—H31B | 0.9800 | C32'—H32B | 1.0000 |
C31—H31C | 0.9800 | C33'—C34' | 1.534 (3) |
C32—C37 | 1.529 (4) | C33'—H33C | 0.9900 |
C32—C33 | 1.540 (3) | C33'—H33D | 0.9900 |
C32—H32A | 1.0000 | C34'—C35' | 1.520 (4) |
C33—C34 | 1.525 (4) | C34'—H34C | 0.9900 |
C33—H33A | 0.9900 | C34'—H34D | 0.9900 |
C33—H33B | 0.9900 | C35'—C36' | 1.526 (4) |
C34—C35 | 1.506 (6) | C35'—H35C | 0.9900 |
C34—H34A | 0.9900 | C35'—H35D | 0.9900 |
C34—H34B | 0.9900 | C36'—C37' | 1.529 (4) |
C35—C36 | 1.512 (5) | C36'—H36C | 0.9900 |
C35—H35A | 0.9900 | C36'—H36D | 0.9900 |
C35—H35B | 0.9900 | C37'—H37C | 0.9900 |
C36—C37 | 1.543 (5) | C37'—H37D | 0.9900 |
C36—H36A | 0.9900 | C38'—N39' | 1.332 (3) |
C36—H36B | 0.9900 | C38'—C43' | 1.387 (4) |
C37—H37A | 0.9900 | N39'—C40' | 1.341 (3) |
C37—H37B | 0.9900 | C40'—C41' | 1.377 (5) |
C38—N39 | 1.322 (3) | C40'—H40B | 0.9500 |
C38—C43 | 1.379 (4) | C41'—N42' | 1.332 (5) |
N39—C40 | 1.336 (3) | C41'—H41B | 0.9500 |
C40—C41 | 1.378 (4) | N42'—C43' | 1.345 (4) |
C40—H40A | 0.9500 | C43'—H43B | 0.9500 |
C41—N42 | 1.316 (4) | C44'—O45' | 1.216 (3) |
C41—H41A | 0.9500 | C44'—N46' | 1.331 (3) |
N42—C43 | 1.334 (3) | N46'—C47' | 1.428 (3) |
C43—H43A | 0.9500 | N46'—H46B | 0.873 (18) |
C44—O45 | 1.230 (3) | C47'—C49' | 1.484 (3) |
C44—N46 | 1.328 (3) | C47'—C48' | 1.487 (3) |
N46—C47 | 1.430 (3) | C47'—H47' | 1.029 (19) |
N46—H46A | 0.882 (17) | C48'—C49' | 1.494 (3) |
C47—C48 | 1.489 (3) | C48'—H48C | 0.9900 |
C47—C49 | 1.490 (2) | C48'—H48D | 0.9900 |
C47—H47 | 0.985 (17) | C49'—H49C | 0.9900 |
C48—C49 | 1.494 (3) | C49'—H49D | 0.9900 |
C9—N1—C5 | 120.7 (2) | C47—C48—C49 | 59.92 (13) |
C9—N1—C2 | 128.64 (19) | C47—C48—H48A | 117.8 |
C5—N1—C2 | 110.23 (19) | C49—C48—H48A | 117.8 |
N1—C2—C3 | 105.8 (2) | C47—C48—H48B | 117.8 |
N1—C2—H2A | 110.6 | C49—C48—H48B | 117.8 |
C3—C2—H2A | 110.6 | H48A—C48—H48B | 114.9 |
N1—C2—H2B | 110.6 | C47—C49—C48 | 59.89 (13) |
C3—C2—H2B | 110.6 | C47—C49—H49A | 117.8 |
H2A—C2—H2B | 108.7 | C48—C49—H49A | 117.8 |
C6—C3—C4 | 105.0 (3) | C47—C49—H49B | 117.8 |
C6—C3—C2 | 120.5 (4) | C48—C49—H49B | 117.8 |
C4—C3—C2 | 104.7 (2) | H49A—C49—H49B | 114.9 |
C6—C3—C6" | 25.8 (3) | C9'—N1'—C5' | 120.11 (19) |
C4—C3—C6" | 99.2 (6) | C9'—N1'—C2' | 128.8 (2) |
C2—C3—C6" | 99.2 (5) | C5'—N1'—C2' | 110.87 (18) |
C6—C3—H3A | 108.7 | N1'—C2'—C3' | 104.1 (2) |
C4—C3—H3A | 108.7 | N1'—C2'—H2C | 110.9 |
C2—C3—H3A | 108.7 | C3'—C2'—H2C | 110.9 |
C6"—C3—H3A | 133.3 | N1'—C2'—H2D | 110.9 |
C6—C3—H3C | 92.6 | C3'—C2'—H2D | 110.9 |
C4—C3—H3C | 117.0 | H2C—C2'—H2D | 109.0 |
C2—C3—H3C | 117.0 | C6X—C3'—C2' | 134.6 (7) |
C6"—C3—H3C | 117.0 | C6X—C3'—C4' | 98.7 (6) |
H3A—C3—H3C | 16.3 | C2'—C3'—C4' | 106.6 (2) |
C8—C4—C5 | 115.3 (2) | C6X—C3'—C6' | 27.8 (5) |
C8—C4—C3 | 105.4 (3) | C2'—C3'—C6' | 107.9 (3) |
C5—C4—C3 | 106.3 (2) | C4'—C3'—C6' | 105.0 (3) |
C8—C4—H4A | 109.9 | C6X—C3'—H3B | 91.0 |
C5—C4—H4A | 109.9 | C2'—C3'—H3B | 112.3 |
C3—C4—H4A | 109.9 | C4'—C3'—H3B | 112.3 |
N1—C5—C11 | 106.7 (2) | C6'—C3'—H3B | 112.3 |
N1—C5—C4 | 103.0 (2) | C6X—C3'—H3D | 104.6 |
C11—C5—C4 | 111.3 (2) | C2'—C3'—H3D | 104.6 |
N1—C5—H5A | 111.8 | C4'—C3'—H3D | 104.6 |
C11—C5—H5A | 111.8 | C6'—C3'—H3D | 126.8 |
C4—C5—H5A | 111.8 | H3B—C3'—H3D | 14.5 |
C3—C6—C7 | 100.7 (4) | C8'—C4'—C5' | 113.8 (2) |
C3—C6—H6A | 111.6 | C8'—C4'—C3' | 104.9 (2) |
C7—C6—H6A | 111.6 | C5'—C4'—C3' | 105.6 (2) |
C3—C6—H6B | 111.6 | C8'—C4'—H4B | 110.8 |
C7—C6—H6B | 111.6 | C5'—C4'—H4B | 110.8 |
H6A—C6—H6B | 109.4 | C3'—C4'—H4B | 110.8 |
C6—C7—C8 | 104.6 (4) | N1'—C5'—C11' | 110.5 (2) |
C6—C7—H7A | 110.8 | N1'—C5'—C4' | 103.1 (2) |
C8—C7—H7A | 110.8 | C11'—C5'—C4' | 111.81 (18) |
C6—C7—H7B | 110.8 | N1'—C5'—H5B | 110.4 |
C8—C7—H7B | 110.8 | C11'—C5'—H5B | 110.4 |
H7A—C7—H7B | 108.9 | C4'—C5'—H5B | 110.4 |
C7"—C6"—C3 | 111.6 (9) | C7'—C6'—C3' | 101.2 (3) |
C7"—C6"—H6"1 | 109.3 | C7'—C6'—H6C | 111.5 |
C3—C6"—H6"1 | 109.3 | C3'—C6'—H6C | 111.5 |
C7"—C6"—H6"2 | 109.3 | C7'—C6'—H6D | 111.5 |
C3—C6"—H6"2 | 109.3 | C3'—C6'—H6D | 111.5 |
H6"1—C6"—H6"2 | 108.0 | H6C—C6'—H6D | 109.3 |
C6"—C7"—C8 | 92.3 (9) | C8'—C7'—C6' | 103.0 (3) |
C6"—C7"—H7"1 | 113.2 | C8'—C7'—H7C | 111.2 |
C8—C7"—H7"1 | 113.2 | C6'—C7'—H7C | 111.2 |
C6"—C7"—H7"2 | 113.2 | C8'—C7'—H7D | 111.2 |
C8—C7"—H7"2 | 113.2 | C6'—C7'—H7D | 111.2 |
H7"1—C7"—H7"2 | 110.6 | H7C—C7'—H7D | 109.1 |
C4—C8—C7 | 103.7 (3) | C6X—C7X—C8' | 97.5 (8) |
C4—C8—C7" | 109.1 (5) | C6X—C7X—H7X1 | 112.3 |
C7—C8—C7" | 30.4 (5) | C8'—C7X—H7X1 | 112.3 |
C4—C8—H8A | 111.0 | C6X—C7X—H7X2 | 112.3 |
C7—C8—H8A | 111.0 | C8'—C7X—H7X2 | 112.3 |
C7"—C8—H8A | 130.6 | H7X1—C7X—H7X2 | 109.9 |
C4—C8—H8B | 111.0 | C3'—C6X—C7X | 104.6 (8) |
C7—C8—H8B | 111.0 | C3'—C6X—H6X1 | 110.8 |
C7"—C8—H8B | 81.5 | C7X—C6X—H6X1 | 110.8 |
H8A—C8—H8B | 109.0 | C3'—C6X—H6X2 | 110.8 |
C4—C8—H8E | 109.9 | C7X—C6X—H6X2 | 110.8 |
C7—C8—H8E | 84.7 | H6X1—C6X—H6X2 | 108.9 |
C7"—C8—H8E | 109.9 | C7'—C8'—C7X | 29.9 (5) |
H8A—C8—H8E | 28.2 | C7'—C8'—C4' | 103.5 (3) |
H8B—C8—H8E | 130.5 | C7X—C8'—C4' | 106.7 (5) |
C4—C8—H8F | 109.9 | C7'—C8'—H8C | 111.1 |
C7—C8—H8F | 136.4 | C7X—C8'—H8C | 132.2 |
C7"—C8—H8F | 109.9 | C4'—C8'—H8C | 111.1 |
H8A—C8—H8F | 82.1 | C7'—C8'—H8D | 111.1 |
H8B—C8—H8F | 30.4 | C7X—C8'—H8D | 82.7 |
H8E—C8—H8F | 108.3 | C4'—C8'—H8D | 111.1 |
O10—C9—N1 | 121.7 (2) | H8C—C8'—H8D | 109.0 |
O10—C9—C13 | 120.2 (2) | C7'—C8'—H8G | 84.6 |
N1—C9—C13 | 118.08 (19) | C7X—C8'—H8G | 110.4 |
O12—C11—N17 | 121.8 (3) | C4'—C8'—H8G | 110.4 |
O12—C11—C5 | 120.5 (3) | H8C—C8'—H8G | 28.1 |
N17—C11—C5 | 117.7 (2) | H8D—C8'—H8G | 130.1 |
N14—C13—C9 | 106.80 (17) | C7'—C8'—H8H | 135.6 |
N14—C13—C22 | 113.03 (19) | C7X—C8'—H8H | 110.4 |
C9—C13—C22 | 112.2 (2) | C4'—C8'—H8H | 110.4 |
N14—C13—H13A | 108.2 | H8C—C8'—H8H | 82.8 |
C9—C13—H13A | 108.2 | H8D—C8'—H8H | 29.4 |
C22—C13—H13A | 108.2 | H8G—C8'—H8H | 108.6 |
C15—N14—C13 | 122.26 (18) | O10'—C9'—N1' | 120.6 (2) |
C15—N14—H14A | 120.8 (18) | O10'—C9'—C13' | 120.35 (18) |
C13—N14—H14A | 115.8 (18) | N1'—C9'—C13' | 119.02 (19) |
O16—C15—N14 | 123.9 (2) | O12'—C11'—N17' | 124.5 (2) |
O16—C15—C24 | 121.1 (2) | O12'—C11'—C5' | 121.9 (2) |
N14—C15—C24 | 114.83 (19) | N17'—C11'—C5' | 113.6 (2) |
C11—N17—C18 | 115.7 (2) | N14'—C13'—C9' | 105.42 (17) |
C11—N17—H17A | 120 (2) | N14'—C13'—C22' | 113.43 (18) |
C18—N17—H17A | 122 (2) | C9'—C13'—C22' | 113.46 (18) |
N17—C18—C19 | 112.1 (2) | N14'—C13'—H13B | 108.1 |
N17—C18—C28 | 109.6 (2) | C9'—C13'—H13B | 108.1 |
C19—C18—C28 | 118.3 (3) | C22'—C13'—H13B | 108.1 |
N17—C18—C19" | 106.8 (9) | C15'—N14'—C13' | 122.30 (18) |
C19—C18—C19" | 37.9 (7) | C15'—N14'—H14B | 116.9 (17) |
C28—C18—C19" | 87.7 (5) | C13'—N14'—H14B | 118.0 (17) |
N17—C18—H18A | 105.2 | O16'—C15'—N14' | 124.2 (2) |
C19—C18—H18A | 105.2 | O16'—C15'—C24' | 120.36 (19) |
C28—C18—H18A | 105.2 | N14'—C15'—C24' | 115.43 (18) |
C19"—C18—H18A | 138.8 | C11'—N17'—C18' | 122.0 (2) |
N17—C18—H18C | 116.3 | C11'—N17'—H17B | 119.1 (19) |
C19—C18—H18C | 82.0 | C18'—N17'—H17B | 118.6 (19) |
C28—C18—H18C | 116.3 | N17'—C18'—C28' | 108.80 (18) |
C19"—C18—H18C | 116.3 | N17'—C18'—C19' | 112.66 (19) |
H18A—C18—H18C | 23.3 | C28'—C18'—C19' | 112.9 (2) |
C18—C19—C20 | 110.8 (3) | N17'—C18'—H18B | 107.4 |
C18—C19—H19A | 109.5 | C28'—C18'—H18B | 107.4 |
C20—C19—H19A | 109.5 | C19'—C18'—H18B | 107.4 |
C18—C19—H19B | 109.5 | C20'—C19'—C18' | 116.4 (2) |
C20—C19—H19B | 109.5 | C20'—C19'—H19C | 108.2 |
H19A—C19—H19B | 108.1 | C18'—C19'—H19C | 108.2 |
C19—C20—C21 | 113.6 (3) | C20'—C19'—H19D | 108.2 |
C19—C20—H20A | 108.8 | C18'—C19'—H19D | 108.2 |
C21—C20—H20A | 108.8 | H19C—C19'—H19D | 107.3 |
C19—C20—H20B | 108.8 | C21'—C20'—C19' | 114.6 (3) |
C21—C20—H20B | 108.8 | C21'—C20'—H20C | 108.6 |
H20A—C20—H20B | 107.7 | C19'—C20'—H20C | 108.6 |
C20"—C19"—C18 | 117.0 (7) | C21'—C20'—H20D | 108.6 |
C20"—C19"—H19E | 108.1 | C19'—C20'—H20D | 108.6 |
C18—C19"—H19E | 108.1 | H20C—C20'—H20D | 107.6 |
C20"—C19"—H19F | 108.1 | C20'—C21'—H21D | 109.5 |
C18—C19"—H19F | 108.1 | C20'—C21'—H21E | 109.5 |
H19E—C19"—H19F | 107.3 | H21D—C21'—H21E | 109.5 |
C21—C20"—C19" | 112.4 (6) | C20'—C21'—H21F | 109.5 |
C21—C20"—H20E | 109.1 | H21D—C21'—H21F | 109.5 |
C19"—C20"—H20E | 109.1 | H21E—C21'—H21F | 109.5 |
C21—C20"—H20F | 109.1 | C30'—C22'—C31' | 109.4 (2) |
C19"—C20"—H20F | 109.1 | C30'—C22'—C23' | 109.9 (2) |
H20E—C20"—H20F | 107.9 | C31'—C22'—C23' | 108.8 (2) |
C20"—C21—C20 | 37.2 (5) | C30'—C22'—C13' | 112.9 (2) |
C20"—C21—H21A | 113.8 | C31'—C22'—C13' | 107.7 (2) |
C20—C21—H21A | 109.5 | C23'—C22'—C13' | 108.0 (2) |
C20"—C21—H21B | 132.5 | C22'—C23'—H23D | 109.5 |
C20—C21—H21B | 109.5 | C22'—C23'—H23E | 109.5 |
H21A—C21—H21B | 109.5 | H23D—C23'—H23E | 109.5 |
C20"—C21—H21C | 73.6 | C22'—C23'—H23F | 109.5 |
C20—C21—H21C | 109.5 | H23D—C23'—H23F | 109.5 |
H21A—C21—H21C | 109.5 | H23E—C23'—H23F | 109.5 |
H21B—C21—H21C | 109.5 | N25'—C24'—C15' | 107.87 (18) |
C30—C22—C31 | 110.3 (3) | N25'—C24'—C32' | 112.34 (17) |
C30—C22—C23 | 109.4 (3) | C15'—C24'—C32' | 109.21 (17) |
C31—C22—C23 | 109.6 (3) | N25'—C24'—H24B | 109.1 |
C30—C22—C13 | 106.9 (2) | C15'—C24'—H24B | 109.1 |
C31—C22—C13 | 109.0 (2) | C32'—C24'—H24B | 109.1 |
C23—C22—C13 | 111.6 (2) | C26'—N25'—C24' | 122.9 (2) |
C22—C23—H23A | 109.5 | C26'—N25'—H25B | 117.0 (19) |
C22—C23—H23B | 109.5 | C24'—N25'—H25B | 119.9 (18) |
H23A—C23—H23B | 109.5 | O27'—C26'—N25' | 123.8 (2) |
C22—C23—H23C | 109.5 | O27'—C26'—C38' | 120.3 (2) |
H23A—C23—H23C | 109.5 | N25'—C26'—C38' | 115.9 (2) |
H23B—C23—H23C | 109.5 | O29'—C28'—C18' | 122.9 (2) |
N25—C24—C15 | 109.37 (19) | O29'—C28'—C44' | 120.9 (2) |
N25—C24—C32 | 110.78 (19) | C18'—C28'—C44' | 116.13 (18) |
C15—C24—C32 | 108.86 (19) | C22'—C30'—H30D | 109.5 |
N25—C24—H24A | 109.3 | C22'—C30'—H30E | 109.5 |
C15—C24—H24A | 109.3 | H30D—C30'—H30E | 109.5 |
C32—C24—H24A | 109.3 | C22'—C30'—H30F | 109.5 |
C26—N25—C24 | 123.18 (19) | H30D—C30'—H30F | 109.5 |
C26—N25—H25A | 119 (2) | H30E—C30'—H30F | 109.5 |
C24—N25—H25A | 118 (2) | C22'—C31'—H31D | 109.5 |
O27—C26—N25 | 124.0 (2) | C22'—C31'—H31E | 109.5 |
O27—C26—C38 | 120.1 (2) | H31D—C31'—H31E | 109.5 |
N25—C26—C38 | 115.8 (2) | C22'—C31'—H31F | 109.5 |
O29—C28—C18 | 121.8 (2) | H31D—C31'—H31F | 109.5 |
O29—C28—C44 | 121.1 (2) | H31E—C31'—H31F | 109.5 |
C18—C28—C44 | 117.1 (2) | C37'—C32'—C33' | 109.89 (19) |
C22—C30—H30A | 109.5 | C37'—C32'—C24' | 110.94 (18) |
C22—C30—H30B | 109.5 | C33'—C32'—C24' | 111.28 (17) |
H30A—C30—H30B | 109.5 | C37'—C32'—H32B | 108.2 |
C22—C30—H30C | 109.5 | C33'—C32'—H32B | 108.2 |
H30A—C30—H30C | 109.5 | C24'—C32'—H32B | 108.2 |
H30B—C30—H30C | 109.5 | C32'—C33'—C34' | 111.25 (19) |
C22—C31—H31A | 109.5 | C32'—C33'—H33C | 109.4 |
C22—C31—H31B | 109.5 | C34'—C33'—H33C | 109.4 |
H31A—C31—H31B | 109.5 | C32'—C33'—H33D | 109.4 |
C22—C31—H31C | 109.5 | C34'—C33'—H33D | 109.4 |
H31A—C31—H31C | 109.5 | H33C—C33'—H33D | 108.0 |
H31B—C31—H31C | 109.5 | C35'—C34'—C33' | 111.6 (2) |
C37—C32—C33 | 110.2 (2) | C35'—C34'—H34C | 109.3 |
C37—C32—C24 | 110.7 (2) | C33'—C34'—H34C | 109.3 |
C33—C32—C24 | 112.0 (2) | C35'—C34'—H34D | 109.3 |
C37—C32—H32A | 107.9 | C33'—C34'—H34D | 109.3 |
C33—C32—H32A | 107.9 | H34C—C34'—H34D | 108.0 |
C24—C32—H32A | 107.9 | C34'—C35'—C36' | 111.5 (2) |
C34—C33—C32 | 111.4 (2) | C34'—C35'—H35C | 109.3 |
C34—C33—H33A | 109.3 | C36'—C35'—H35C | 109.3 |
C32—C33—H33A | 109.3 | C34'—C35'—H35D | 109.3 |
C34—C33—H33B | 109.3 | C36'—C35'—H35D | 109.3 |
C32—C33—H33B | 109.3 | H35C—C35'—H35D | 108.0 |
H33A—C33—H33B | 108.0 | C35'—C36'—C37' | 110.5 (2) |
C35—C34—C33 | 111.2 (3) | C35'—C36'—H36C | 109.6 |
C35—C34—H34A | 109.4 | C37'—C36'—H36C | 109.6 |
C33—C34—H34A | 109.4 | C35'—C36'—H36D | 109.6 |
C35—C34—H34B | 109.4 | C37'—C36'—H36D | 109.6 |
C33—C34—H34B | 109.4 | H36C—C36'—H36D | 108.1 |
H34A—C34—H34B | 108.0 | C36'—C37'—C32' | 111.4 (2) |
C34—C35—C36 | 111.0 (4) | C36'—C37'—H37C | 109.4 |
C34—C35—H35A | 109.4 | C32'—C37'—H37C | 109.4 |
C36—C35—H35A | 109.4 | C36'—C37'—H37D | 109.4 |
C34—C35—H35B | 109.4 | C32'—C37'—H37D | 109.4 |
C36—C35—H35B | 109.4 | H37C—C37'—H37D | 108.0 |
H35A—C35—H35B | 108.0 | N39'—C38'—C43' | 122.5 (2) |
C35—C36—C37 | 110.5 (3) | N39'—C38'—C26' | 118.1 (2) |
C35—C36—H36A | 109.6 | C43'—C38'—C26' | 119.4 (2) |
C37—C36—H36A | 109.6 | C38'—N39'—C40' | 115.9 (3) |
C35—C36—H36B | 109.6 | N39'—C40'—C41' | 121.6 (3) |
C37—C36—H36B | 109.6 | N39'—C40'—H40B | 119.2 |
H36A—C36—H36B | 108.1 | C41'—C40'—H40B | 119.2 |
C32—C37—C36 | 111.3 (3) | N42'—C41'—C40' | 123.0 (3) |
C32—C37—H37A | 109.4 | N42'—C41'—H41B | 118.5 |
C36—C37—H37A | 109.4 | C40'—C41'—H41B | 118.5 |
C32—C37—H37B | 109.4 | C41'—N42'—C43' | 115.5 (3) |
C36—C37—H37B | 109.4 | N42'—C43'—C38' | 121.5 (3) |
H37A—C37—H37B | 108.0 | N42'—C43'—H43B | 119.3 |
N39—C38—C43 | 121.3 (2) | C38'—C43'—H43B | 119.3 |
N39—C38—C26 | 118.1 (2) | O45'—C44'—N46' | 126.1 (2) |
C43—C38—C26 | 120.5 (2) | O45'—C44'—C28' | 119.8 (2) |
C38—N39—C40 | 115.6 (2) | N46'—C44'—C28' | 114.04 (19) |
N39—C40—C41 | 122.5 (2) | C44'—N46'—C47' | 119.7 (2) |
N39—C40—H40A | 118.8 | C44'—N46'—H46B | 120 (2) |
C41—C40—H40A | 118.8 | C47'—N46'—H46B | 121 (2) |
N42—C41—C40 | 122.1 (2) | N46'—C47'—C49' | 119.9 (3) |
N42—C41—H41A | 118.9 | N46'—C47'—C48' | 118.4 (2) |
C40—C41—H41A | 118.9 | C49'—C47'—C48' | 60.36 (14) |
C41—N42—C43 | 115.2 (2) | N46'—C47'—H47' | 119 (2) |
N42—C43—C38 | 123.1 (3) | C49'—C47'—H47' | 116 (2) |
N42—C43—H43A | 118.4 | C48'—C47'—H47' | 109 (2) |
C38—C43—H43A | 118.4 | C47'—C48'—C49' | 59.72 (14) |
O45—C44—N46 | 126.3 (2) | C47'—C48'—H48C | 117.8 |
O45—C44—C28 | 120.0 (2) | C49'—C48'—H48C | 117.8 |
N46—C44—C28 | 113.65 (19) | C47'—C48'—H48D | 117.8 |
C44—N46—C47 | 121.85 (19) | C49'—C48'—H48D | 117.8 |
C44—N46—H46A | 118.1 (18) | H48C—C48'—H48D | 114.9 |
C47—N46—H46A | 120.0 (18) | C47'—C49'—C48' | 59.92 (14) |
N46—C47—C48 | 119.9 (2) | C47'—C49'—H49C | 117.8 |
N46—C47—C49 | 119.9 (2) | C48'—C49'—H49C | 117.8 |
C48—C47—C49 | 60.19 (14) | C47'—C49'—H49D | 117.8 |
N46—C47—H47 | 115.4 (16) | C48'—C49'—H49D | 117.8 |
C48—C47—H47 | 117.1 (16) | H49C—C49'—H49D | 114.9 |
C49—C47—H47 | 113.1 (16) | ||
C4—C5—C11—N17 | −127.8 (3) | C44'—N46'—C47'—C49' | −84.7 (3) |
C4'—C5'—C11'—N17' | −82.5 (3) | C44—N46—C47—C48 | −140.1 (3) |
C18—C19—C20—C21 | −176.6 (3) | C44'—N46'—C47'—C48' | −155.0 (3) |
C18'—C19'—C20'—C21' | 88.1 (3) | C32—C24—N25—C26 | 124.8 (2) |
C44—N46—C47—C49 | 149.2 (2) | C32'—C24'—N25'—C26' | 105.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14A···O29′ | 0.86 (2) | 2.12 (2) | 2.958 (2) | 165 (2) |
N17—H17A···O27′i | 0.87 (2) | 2.13 (2) | 2.928 (3) | 153 (3) |
N46—H46A···O10′i | 0.88 (2) | 2.09 (2) | 2.941 (2) | 163 (3) |
N14′—H14B···O29ii | 0.88 (2) | 2.07 (2) | 2.945 (3) | 170 (2) |
N17′—H17B···O27 | 0.86 (2) | 2.08 (2) | 2.912 (3) | 162 (3) |
N46′—H46B···O10 | 0.87 (2) | 2.22 (2) | 3.051 (3) | 160 (3) |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C36H53N7O6 |
Mr | 679.85 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 10.4235 (2), 19.1651 (2), 37.2907 (4) |
V (Å3) | 7449.47 (18) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.10 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Agilent Xcalibur Ruby Gemini ultra diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.861, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28223, 13136, 12517 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.121, 1.03 |
No. of reflections | 13136 |
No. of parameters | 945 |
No. of restraints | 41 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.54, −0.49 |
Absolute structure | Flack (1983), 5813 Friedel pairs |
Absolute structure parameter | −0.01 (15) |
Computer programs: CrysAlis PRO (Agilent, 2011), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Bruker, 1998) and Mercury (Bruno et al., 2002), publCIF (Westrip, 2010).
C4—C5—C11—N17 | −127.8 (3) | C44'—N46'—C47'—C49' | −84.7 (3) |
C4'—C5'—C11'—N17' | −82.5 (3) | C44—N46—C47—C48 | −140.1 (3) |
C18—C19—C20—C21 | −176.6 (3) | C44'—N46'—C47'—C48' | −155.0 (3) |
C18'—C19'—C20'—C21' | 88.1 (3) | C32—C24—N25—C26 | 124.8 (2) |
C44—N46—C47—C49 | 149.2 (2) | C32'—C24'—N25'—C26' | 105.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14A···O29' | 0.858 (17) | 2.121 (18) | 2.958 (2) | 165 (2) |
N17—H17A···O27'i | 0.870 (18) | 2.13 (2) | 2.928 (3) | 153 (3) |
N46—H46A···O10'i | 0.882 (17) | 2.088 (19) | 2.941 (2) | 163 (3) |
N14'—H14B···O29ii | 0.883 (17) | 2.071 (18) | 2.945 (3) | 170 (2) |
N17'—H17B···O27 | 0.859 (18) | 2.08 (2) | 2.912 (3) | 162 (3) |
N46'—H46B···O10 | 0.873 (18) | 2.22 (2) | 3.051 (3) | 160 (3) |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1/2, −y+1, z+1/2. |
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Telaprevir, (I), is a new antiviral drug for the treatment of hepatitis C. It acts as a highly selective potent inhibitor of the hepatitis C viral enzyme NS3–4 A serine protease (Revill et al., 2007; Kwong et al., 2011). The title compound (brand name: Incivek, Vertex Pharmaceuticals) has been approved by the US Food and Drug Administration (FDA) for use in the United States in 2011. About 170 million patients (3% of the world population) are chronically infected with hepatitis C (Lavanchy, 1999) and telaprevir is indicated for the treatment of genotype 1 infection which is the most common form of this disease in developed countries. Procedures for the synthesis of (I) have been described by Yip et al. (2004) and Znabet et al. (2010).
The molecule of the optically active compound (I) contains six chiral centers. A screening programme involving various crystallization methods and more than 70 solvents indicated the existence of just a single unsolvated crystalline form of (I) (European Medicines Agency, 2011).
The asymmetric unit of (I) comprises two molecules, denoted A and B (Fig. 1). Matching numbering schemes (C1/C1', C2/C2' etc.) were used for the corresponding atomic positions in molecules A and B. Chiral centers and potential donor and acceptor groups for hydrogen bonds are highlighted in the Scheme.
The A and B molecules exhibit distinct conformations. An overlay (Fig. 2) shows that they differ mainly in the rotation angles about four single bonds, viz. C5—C11, C19—C20 (conformation of the propyl chain), N46—C47 (orientation of the cyclopropyl ring) and C24—C25. The corresponding torsion angles are collected in Table 1. Fig. 2 indicates that the overall molecular shape is affected most by a 45° change in torsion angle θ1, defined by C4—C5—C11—N17 (in molecule A) and C4'—C5'—C11'—N17' (in molecule B). Additionally, the two molecules differ in the geometry of the cyclopenta[c]pyrrolidine unit. Therefore, ring puckering parameters (Cremer & Pople, 1975) have been calculated for the five-membered pyrrolidine (N1/C2–C5) and cyclopentane (C3/C4/C8/C7/C6) rings using PLATON (Spek, 2009). In molecule A, the pyrrolidine ring adopts an approximate C5-envelope conformation [q2 = 0.302 (3) Å and ϕ2 = 138.8 (6)°] and in molecule B it is an approximate N1-envelope [q2 = 0.293 (3) Å and ϕ2 = 171.4 (6)°]. As illustrated in Figs. 3a and 3b, the cyclopentane ring is disordered between a C6-envelope [molecule A: q2 = 0.434 (5) Å and ϕ2 = 321.0 (6)°; molecule B: q2 = 0.500 (9) Å and ϕ2 = 319.2 (10)°] and a C7-envelope conformation [molecule A: q2 = 0.459 (9) Å and ϕ2 = 109 (1)°; molecule B: q2 = 0.456 (4) Å and ϕ2 = 110.7 (5)°] in each molecule. The occupancy ratio of the disorder fragments was found to be 70:30 in each case, but the C6-envelope conformation is the main component of molecule A, whilst the main component of molecule B has the C7-envelope conformation. The geometry of the propyl chain in molecule A is such that the conformation of the C—C—C—C unit involving positions 18—21 is nearly ideally trans (Table 1). This chain exists in two distinct orientations (occupancy ratio 75:25; Fig. 3c), whose nearly planar C—C—C—C fragments form an angle of 54 (2)° with one another. They form two rather similar angles of 75.7 (7) and 67.8 (2)° with the adjacent planar C18—C28(═O29)—C44) unit. In contrast to the trans conformation found in molecule A, the C18'—C19'—C20'—C21' torsion angle characterizing the conformation of the propyl chain in molecule B is 88.1 (3)°.
The molecule of (I) contains four NH groups and six carbonyl O atoms which are potential donor and acceptor sites, respectively, for hydrogen bonds. The independent molecules A and B have the same hydrogen-bond connectivity mode involving six N—H···O bonds per molecule (Table 2). Specifically, the NH groups at positions 14, 17 and 26 (see Scheme) in the A-type molecule are bonded to carbonyl O sites 29, 27 and 10, respectively, of B molecules and vice versa (Fig. 4). Molecule A is linked, via two three-point connections, to two B molecules so that a helical chain is formed which propagates along the [001] direction (Fig. 5). Each connection consists of two N—H···O hydrogen-bonded rings that are described as R22(10) and R22(12) in Etter's graph-set notation (Etter et al., 1990; Bernstein et al., 1995). These rings are additionally fused together into a larger R22(16) unit. A prerequisite for the three-point N—H···O connection is the geometrical match between complementary hydrogen-bond donor and acceptor groups situated at opposite ends of the molecule. However, the NH group at position 25 is not engaged in hydrogen bonding despite an abundance of potential acceptor sites in this structure. This may be a trade-off effect of the inherently favourable N—H···O three-point connections which impose geometrical constraints both on the individual molecule and on the hydrogen-bonded chain as a whole. The formation of close intermolecular contacts between the free NH group at position N25 and a carbonyl group may not be feasible under these circumstances.
The highest anomalous contribution to the intensity data of (I) comes from O atoms. Copper radiation was used for the data collection to enable a determination of the absolute structure even under these circumstances. Refinement of the absolute structure parameter x (Flack, 1983) gave a value of -0.01 (15) for 5813 Friedel pairs (97% Friedel coverage). Additionally, a Bayesian statistics analysis on Bijvoet differences was performed using the program PLATON (Spek, 2009). The obtained Hooft parameter y (Hooft et al., 2008) was 0.01 (5) and the probability levels of having an incorrect attribution, P2 (racemic twin) and P3 (false), were both essentially zero. These results clearly indicate that the correct enantiomer has been determined. This assignment of the chiral centers is also in agreement with the synthetic procedure.