The asymmetric unit of the title compound, C
25H
20N
2O
2, contains an enantiomeric pair of molecules, which are linked by N—H
O hydrogen bonds involving N—H and C=O groups of the pyrrole ring. In both molecules, the central six-membered ring of the anthrone moiety adopts a boat conformation, the pyrrolidine ring adopts an envelope conformation and the five-membered ring in the oxindole moiety is slightly distorted from planarity. Both the anthrone and oxindole moieties are almost perpendicular to the pyrrolidine ring.
Supporting information
CCDC reference: 193727
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.124
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995).
1'-Methylindole-3-spiro-2'-pyrrolidine-3'-spiro-9''-anthracene-2,10''-dione
top
Crystal data top
C25H20N2O2 | F(000) = 1600 |
Mr = 380.43 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.338 (1) Å | θ = 15–30° |
b = 28.339 (4) Å | µ = 0.67 mm−1 |
c = 17.045 (2) Å | T = 293 K |
β = 108.18 (1)° | Needle, orange |
V = 3826.5 (9) Å3 | 0.36 × 0.30 × 0.13 mm |
Z = 8 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 6411 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 72.0°, θmin = 3.1° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −34→0 |
Tmin = 0.794, Tmax = 0.918 | l = −21→19 |
8049 measured reflections | 3 standard reflections every 120min min |
7521 independent reflections | intensity decay: <1% |
Refinement top
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.068P)2 + 0.7213P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
7521 reflections | Δρmax = 0.21 e Å−3 |
524 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (2) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | −0.49511 (13) | 0.45983 (4) | 0.17284 (8) | 0.0448 (3) | |
C2A | −0.31151 (15) | 0.45985 (5) | 0.19959 (8) | 0.0393 (3) | |
C3A | −0.27047 (16) | 0.50523 (5) | 0.25827 (8) | 0.0426 (3) | |
C4A | −0.40742 (19) | 0.50002 (6) | 0.30196 (10) | 0.0549 (4) | |
H4A | −0.3609 | 0.4845 | 0.3549 | 0.066* | |
H4B | −0.4496 | 0.5308 | 0.3111 | 0.066* | |
C5A | −0.54968 (19) | 0.47029 (6) | 0.24461 (11) | 0.0566 (4) | |
H5A | −0.5656 | 0.4414 | 0.2718 | 0.068* | |
H5B | −0.6549 | 0.4878 | 0.2283 | 0.068* | |
N6A | −0.11994 (15) | 0.39693 (4) | 0.21408 (8) | 0.0467 (3) | |
H6A | −0.0541 | 0.3735 | 0.2339 | 0.056* | |
C7A | −0.23099 (17) | 0.41487 (5) | 0.24890 (9) | 0.0433 (3) | |
C8A | −0.23783 (15) | 0.45854 (5) | 0.12927 (8) | 0.0379 (3) | |
C9A | −0.27277 (17) | 0.48475 (5) | 0.05745 (8) | 0.0424 (3) | |
H9A | −0.3499 | 0.5095 | 0.0475 | 0.051* | |
C10A | −0.19030 (19) | 0.47348 (5) | 0.00031 (9) | 0.0490 (3) | |
H10A | −0.2118 | 0.4910 | −0.0480 | 0.059* | |
C11A | −0.0768 (2) | 0.43646 (6) | 0.01471 (10) | 0.0530 (4) | |
H11A | −0.0223 | 0.4297 | −0.0240 | 0.064* | |
C12A | −0.04261 (18) | 0.40934 (6) | 0.08543 (10) | 0.0493 (3) | |
H12A | 0.0327 | 0.3842 | 0.0947 | 0.059* | |
C13A | −0.12464 (16) | 0.42103 (5) | 0.14175 (8) | 0.0408 (3) | |
C14A | 0.03908 (18) | 0.52835 (6) | 0.29574 (10) | 0.0507 (4) | |
C15A | 0.00238 (19) | 0.55688 (6) | 0.21996 (10) | 0.0536 (4) | |
C16A | −0.17462 (18) | 0.57138 (5) | 0.18149 (9) | 0.0460 (3) | |
C17A | −0.2077 (2) | 0.60879 (5) | 0.12588 (10) | 0.0561 (4) | |
H17A | −0.1194 | 0.6232 | 0.1125 | 0.067* | |
C18A | −0.3702 (2) | 0.62459 (6) | 0.09062 (12) | 0.0627 (4) | |
H18A | −0.3926 | 0.6494 | 0.0530 | 0.075* | |
C19A | −0.4997 (2) | 0.60327 (6) | 0.11166 (11) | 0.0620 (4) | |
H19A | −0.6098 | 0.6140 | 0.0884 | 0.074* | |
C20A | −0.46785 (19) | 0.56608 (5) | 0.16694 (10) | 0.0522 (4) | |
H20A | −0.5570 | 0.5523 | 0.1804 | 0.063* | |
C21A | −0.30468 (17) | 0.54888 (5) | 0.20295 (9) | 0.0430 (3) | |
C22A | −0.08906 (17) | 0.50422 (5) | 0.31659 (9) | 0.0460 (3) | |
C23A | −0.0424 (2) | 0.47828 (7) | 0.39009 (10) | 0.0587 (4) | |
H23A | −0.1243 | 0.4616 | 0.4051 | 0.070* | |
C24A | 0.1234 (2) | 0.47692 (8) | 0.44085 (11) | 0.0722 (5) | |
H24A | 0.1519 | 0.4590 | 0.4889 | 0.087* | |
C25A | 0.2465 (2) | 0.50199 (8) | 0.42067 (13) | 0.0778 (6) | |
H25A | 0.3573 | 0.5016 | 0.4556 | 0.093* | |
C26A | 0.2049 (2) | 0.52740 (7) | 0.34882 (12) | 0.0669 (5) | |
H26A | 0.2881 | 0.5443 | 0.3352 | 0.080* | |
O27A | 0.11541 (16) | 0.56982 (6) | 0.19316 (10) | 0.0814 (4) | |
O28A | −0.26526 (13) | 0.39775 (4) | 0.30801 (7) | 0.0545 (3) | |
C29A | −0.5758 (2) | 0.41907 (6) | 0.12513 (12) | 0.0615 (4) | |
H29A | −0.5332 | 0.4147 | 0.0794 | 0.092* | |
H29B | −0.6956 | 0.4240 | 0.1048 | 0.092* | |
H29C | −0.5520 | 0.3915 | 0.1596 | 0.092* | |
N1B | 0.45909 (17) | 0.33457 (4) | 0.45321 (8) | 0.0529 (3) | |
C2B | 0.29677 (18) | 0.31563 (5) | 0.45221 (9) | 0.0444 (3) | |
C3B | 0.32149 (18) | 0.26031 (5) | 0.43940 (8) | 0.0426 (3) | |
C4B | 0.4225 (2) | 0.26258 (6) | 0.37706 (9) | 0.0524 (4) | |
H4C | 0.5041 | 0.2371 | 0.3872 | 0.063* | |
H4D | 0.3470 | 0.2598 | 0.3210 | 0.063* | |
C5B | 0.5124 (2) | 0.31031 (6) | 0.38945 (11) | 0.0613 (4) | |
H5C | 0.6339 | 0.3061 | 0.4074 | 0.074* | |
H5D | 0.4798 | 0.3283 | 0.3385 | 0.074* | |
N6B | 0.01888 (17) | 0.34544 (5) | 0.41139 (8) | 0.0546 (3) | |
H6B | −0.0818 | 0.3532 | 0.3821 | 0.065* | |
C7B | 0.1432 (2) | 0.33300 (5) | 0.37983 (9) | 0.0490 (3) | |
C8B | 0.24217 (19) | 0.32874 (5) | 0.52561 (9) | 0.0464 (3) | |
C9B | 0.3289 (2) | 0.32870 (6) | 0.60924 (10) | 0.0551 (4) | |
H9B | 0.4420 | 0.3200 | 0.6285 | 0.066* | |
C10B | 0.2430 (3) | 0.34193 (7) | 0.66417 (11) | 0.0673 (5) | |
H10B | 0.2992 | 0.3419 | 0.7207 | 0.081* | |
C11B | 0.0757 (3) | 0.35499 (7) | 0.63542 (12) | 0.0721 (5) | |
H11B | 0.0199 | 0.3628 | 0.6731 | 0.087* | |
C12B | −0.0113 (3) | 0.35680 (7) | 0.55198 (11) | 0.0667 (5) | |
H12B | −0.1237 | 0.3662 | 0.5328 | 0.080* | |
C13B | 0.0757 (2) | 0.34408 (5) | 0.49801 (10) | 0.0509 (3) | |
C14B | 0.07140 (19) | 0.21972 (5) | 0.46437 (10) | 0.0495 (3) | |
C15B | 0.1609 (2) | 0.22070 (6) | 0.55408 (10) | 0.0533 (4) | |
C16B | 0.34694 (19) | 0.22338 (5) | 0.57821 (9) | 0.0457 (3) | |
C17B | 0.4409 (2) | 0.20771 (6) | 0.65676 (10) | 0.0565 (4) | |
H17B | 0.3858 | 0.1974 | 0.6934 | 0.068* | |
C18B | 0.6137 (2) | 0.20745 (6) | 0.68031 (11) | 0.0652 (5) | |
H18B | 0.6761 | 0.1968 | 0.7325 | 0.078* | |
C19B | 0.6945 (2) | 0.22317 (7) | 0.62573 (11) | 0.0639 (4) | |
H19B | 0.8117 | 0.2224 | 0.6410 | 0.077* | |
C20B | 0.6024 (2) | 0.24002 (6) | 0.54847 (10) | 0.0532 (4) | |
H20B | 0.6590 | 0.2515 | 0.5132 | 0.064* | |
C21B | 0.42693 (18) | 0.24012 (5) | 0.52279 (9) | 0.0433 (3) | |
C22B | 0.15066 (18) | 0.23538 (5) | 0.40778 (9) | 0.0452 (3) | |
C23B | 0.0640 (2) | 0.22921 (6) | 0.32404 (10) | 0.0569 (4) | |
H23B | 0.1127 | 0.2394 | 0.2849 | 0.068* | |
C24B | −0.0935 (2) | 0.20810 (7) | 0.29838 (12) | 0.0664 (5) | |
H24B | −0.1479 | 0.2038 | 0.2423 | 0.080* | |
C25B | −0.1708 (2) | 0.19342 (7) | 0.35470 (13) | 0.0697 (5) | |
H25B | −0.2774 | 0.1797 | 0.3368 | 0.084* | |
C26B | −0.0891 (2) | 0.19929 (6) | 0.43745 (12) | 0.0625 (4) | |
H26B | −0.1407 | 0.1896 | 0.4759 | 0.075* | |
O27B | 0.08686 (18) | 0.21620 (6) | 0.60528 (8) | 0.0808 (4) | |
O28B | 0.13585 (15) | 0.33517 (4) | 0.30720 (7) | 0.0612 (3) | |
C29B | 0.4689 (3) | 0.38576 (6) | 0.45060 (14) | 0.0730 (5) | |
H29D | 0.4323 | 0.3991 | 0.4939 | 0.109* | |
H29E | 0.3976 | 0.3969 | 0.3981 | 0.109* | |
H29F | 0.5834 | 0.3951 | 0.4580 | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0319 (5) | 0.0461 (6) | 0.0571 (7) | 0.0007 (5) | 0.0148 (5) | 0.0039 (5) |
C2A | 0.0331 (6) | 0.0420 (7) | 0.0434 (7) | 0.0027 (5) | 0.0129 (5) | 0.0042 (5) |
C3A | 0.0362 (6) | 0.0499 (8) | 0.0438 (7) | 0.0041 (6) | 0.0156 (5) | −0.0021 (6) |
C4A | 0.0470 (8) | 0.0701 (10) | 0.0548 (9) | 0.0087 (7) | 0.0264 (7) | 0.0011 (7) |
C5A | 0.0419 (8) | 0.0651 (10) | 0.0697 (10) | 0.0032 (7) | 0.0273 (7) | 0.0084 (8) |
N6A | 0.0434 (6) | 0.0461 (6) | 0.0518 (7) | 0.0114 (5) | 0.0167 (5) | 0.0105 (5) |
C7A | 0.0381 (6) | 0.0468 (7) | 0.0452 (7) | 0.0021 (6) | 0.0132 (5) | 0.0052 (6) |
C8A | 0.0328 (6) | 0.0390 (6) | 0.0409 (7) | −0.0015 (5) | 0.0103 (5) | −0.0007 (5) |
C9A | 0.0405 (7) | 0.0413 (7) | 0.0429 (7) | −0.0018 (5) | 0.0093 (5) | 0.0015 (5) |
C10A | 0.0508 (8) | 0.0543 (8) | 0.0421 (7) | −0.0081 (6) | 0.0147 (6) | 0.0025 (6) |
C11A | 0.0516 (8) | 0.0611 (9) | 0.0532 (8) | −0.0047 (7) | 0.0264 (7) | −0.0050 (7) |
C12A | 0.0413 (7) | 0.0521 (8) | 0.0573 (9) | 0.0041 (6) | 0.0192 (6) | −0.0036 (7) |
C13A | 0.0341 (6) | 0.0431 (7) | 0.0441 (7) | 0.0000 (5) | 0.0108 (5) | 0.0012 (5) |
C14A | 0.0372 (7) | 0.0605 (9) | 0.0544 (8) | 0.0056 (6) | 0.0142 (6) | −0.0143 (7) |
C15A | 0.0437 (7) | 0.0588 (9) | 0.0635 (9) | −0.0015 (7) | 0.0241 (7) | −0.0102 (7) |
C16A | 0.0455 (7) | 0.0428 (7) | 0.0512 (8) | −0.0025 (6) | 0.0174 (6) | −0.0099 (6) |
C17A | 0.0645 (10) | 0.0450 (8) | 0.0613 (9) | −0.0089 (7) | 0.0231 (8) | −0.0070 (7) |
C18A | 0.0738 (11) | 0.0399 (8) | 0.0670 (10) | −0.0013 (7) | 0.0111 (9) | 0.0014 (7) |
C19A | 0.0546 (9) | 0.0427 (8) | 0.0762 (11) | 0.0060 (7) | 0.0023 (8) | −0.0017 (7) |
C20A | 0.0408 (7) | 0.0441 (8) | 0.0676 (10) | 0.0025 (6) | 0.0110 (7) | −0.0039 (7) |
C21A | 0.0389 (7) | 0.0419 (7) | 0.0473 (7) | 0.0018 (5) | 0.0122 (6) | −0.0083 (6) |
C22A | 0.0397 (7) | 0.0548 (8) | 0.0427 (7) | 0.0068 (6) | 0.0116 (6) | −0.0089 (6) |
C23A | 0.0569 (9) | 0.0711 (11) | 0.0451 (8) | 0.0099 (8) | 0.0114 (7) | −0.0053 (7) |
C24A | 0.0665 (11) | 0.0898 (14) | 0.0496 (9) | 0.0224 (10) | 0.0026 (8) | −0.0090 (9) |
C25A | 0.0463 (9) | 0.1028 (15) | 0.0687 (12) | 0.0168 (10) | −0.0046 (8) | −0.0209 (11) |
C26A | 0.0385 (8) | 0.0847 (12) | 0.0740 (12) | 0.0064 (8) | 0.0125 (8) | −0.0188 (10) |
O27A | 0.0541 (7) | 0.1014 (11) | 0.1019 (11) | −0.0017 (7) | 0.0437 (7) | 0.0086 (8) |
O28A | 0.0519 (6) | 0.0610 (6) | 0.0544 (6) | 0.0074 (5) | 0.0223 (5) | 0.0174 (5) |
C29A | 0.0426 (8) | 0.0543 (9) | 0.0819 (12) | −0.0076 (7) | 0.0111 (8) | −0.0005 (8) |
N1B | 0.0558 (7) | 0.0457 (7) | 0.0618 (8) | 0.0022 (5) | 0.0248 (6) | 0.0079 (6) |
C2B | 0.0500 (8) | 0.0408 (7) | 0.0445 (7) | 0.0078 (6) | 0.0177 (6) | 0.0060 (6) |
C3B | 0.0472 (7) | 0.0413 (7) | 0.0427 (7) | 0.0076 (6) | 0.0189 (6) | 0.0020 (5) |
C4B | 0.0565 (9) | 0.0589 (9) | 0.0487 (8) | 0.0071 (7) | 0.0264 (7) | 0.0022 (7) |
C5B | 0.0632 (10) | 0.0664 (10) | 0.0642 (10) | 0.0028 (8) | 0.0344 (8) | 0.0085 (8) |
N6B | 0.0548 (7) | 0.0599 (8) | 0.0505 (7) | 0.0178 (6) | 0.0185 (6) | 0.0094 (6) |
C7B | 0.0579 (8) | 0.0446 (7) | 0.0464 (8) | 0.0118 (6) | 0.0192 (6) | 0.0079 (6) |
C8B | 0.0575 (8) | 0.0374 (7) | 0.0468 (8) | 0.0064 (6) | 0.0197 (6) | 0.0008 (5) |
C9B | 0.0669 (10) | 0.0490 (8) | 0.0478 (8) | 0.0058 (7) | 0.0154 (7) | −0.0040 (6) |
C10B | 0.0911 (13) | 0.0637 (10) | 0.0475 (9) | 0.0071 (9) | 0.0222 (9) | −0.0108 (8) |
C11B | 0.0917 (14) | 0.0735 (12) | 0.0617 (11) | 0.0142 (10) | 0.0392 (10) | −0.0103 (9) |
C12B | 0.0701 (11) | 0.0722 (11) | 0.0648 (11) | 0.0196 (9) | 0.0312 (9) | −0.0019 (9) |
C13B | 0.0597 (9) | 0.0456 (8) | 0.0503 (8) | 0.0105 (7) | 0.0215 (7) | 0.0028 (6) |
C14B | 0.0476 (8) | 0.0460 (8) | 0.0573 (9) | 0.0065 (6) | 0.0197 (7) | 0.0013 (6) |
C15B | 0.0603 (9) | 0.0518 (8) | 0.0543 (9) | 0.0024 (7) | 0.0272 (7) | 0.0045 (7) |
C16B | 0.0561 (8) | 0.0384 (7) | 0.0447 (7) | 0.0065 (6) | 0.0187 (6) | 0.0025 (6) |
C17B | 0.0740 (11) | 0.0479 (8) | 0.0480 (8) | 0.0067 (7) | 0.0198 (8) | 0.0061 (6) |
C18B | 0.0742 (11) | 0.0614 (10) | 0.0515 (9) | 0.0153 (9) | 0.0073 (8) | 0.0084 (7) |
C19B | 0.0522 (9) | 0.0684 (11) | 0.0646 (10) | 0.0142 (8) | 0.0088 (8) | 0.0026 (8) |
C20B | 0.0501 (8) | 0.0544 (9) | 0.0568 (9) | 0.0082 (7) | 0.0191 (7) | 0.0020 (7) |
C21B | 0.0487 (7) | 0.0374 (7) | 0.0454 (7) | 0.0085 (6) | 0.0172 (6) | 0.0010 (5) |
C22B | 0.0483 (7) | 0.0408 (7) | 0.0476 (7) | 0.0096 (6) | 0.0163 (6) | 0.0009 (6) |
C23B | 0.0598 (9) | 0.0565 (9) | 0.0518 (8) | 0.0088 (7) | 0.0137 (7) | 0.0009 (7) |
C24B | 0.0598 (10) | 0.0661 (11) | 0.0615 (10) | 0.0081 (8) | 0.0019 (8) | −0.0040 (8) |
C25B | 0.0485 (9) | 0.0697 (11) | 0.0838 (13) | 0.0014 (8) | 0.0103 (9) | −0.0052 (10) |
C26B | 0.0505 (9) | 0.0609 (10) | 0.0795 (12) | 0.0039 (7) | 0.0252 (8) | 0.0022 (8) |
O27B | 0.0745 (8) | 0.1139 (11) | 0.0668 (8) | −0.0077 (8) | 0.0406 (7) | 0.0076 (8) |
O28B | 0.0733 (7) | 0.0663 (7) | 0.0469 (6) | 0.0231 (6) | 0.0229 (5) | 0.0155 (5) |
C29B | 0.0785 (12) | 0.0491 (9) | 0.0954 (14) | −0.0037 (9) | 0.0331 (11) | 0.0095 (9) |
Geometric parameters (Å, º) top
N1A—C29A | 1.452 (2) | N1B—C2B | 1.4511 (19) |
N1A—C2A | 1.4546 (16) | N1B—C29B | 1.454 (2) |
N1A—C5A | 1.463 (2) | N1B—C5B | 1.467 (2) |
C2A—C8A | 1.5084 (18) | C2B—C8B | 1.5054 (19) |
C2A—C7A | 1.5587 (18) | C2B—C7B | 1.555 (2) |
C2A—C3A | 1.5992 (19) | C2B—C3B | 1.6050 (19) |
C3A—C21A | 1.527 (2) | C3B—C22B | 1.529 (2) |
C3A—C22A | 1.5293 (19) | C3B—C21B | 1.5300 (19) |
C3A—C4A | 1.5528 (18) | C3B—C4B | 1.5497 (18) |
C4A—C5A | 1.532 (2) | C4B—C5B | 1.529 (2) |
C4A—H4A | 0.97 | C4B—H4C | 0.97 |
C4A—H4B | 0.97 | C4B—H4D | 0.97 |
C5A—H5A | 0.97 | C5B—H5C | 0.97 |
C5A—H5B | 0.97 | C5B—H5D | 0.97 |
N6A—C7A | 1.3459 (18) | N6B—C7B | 1.3556 (19) |
N6A—C13A | 1.3992 (18) | N6B—C13B | 1.403 (2) |
N6A—H6A | 0.86 | N6B—H6B | 0.86 |
C7A—O28A | 1.2295 (17) | C7B—O28B | 1.2215 (18) |
C8A—C9A | 1.3830 (18) | C8B—C9B | 1.382 (2) |
C8A—C13A | 1.3932 (18) | C8B—C13B | 1.389 (2) |
C9A—C10A | 1.393 (2) | C9B—C10B | 1.396 (2) |
C9A—H9A | 0.93 | C9B—H9B | 0.93 |
C10A—C11A | 1.383 (2) | C10B—C11B | 1.377 (3) |
C10A—H10A | 0.93 | C10B—H10B | 0.93 |
C11A—C12A | 1.382 (2) | C11B—C12B | 1.381 (3) |
C11A—H11A | 0.93 | C11B—H11B | 0.93 |
C12A—C13A | 1.3816 (19) | C12B—C13B | 1.385 (2) |
C12A—H12A | 0.93 | C12B—H12B | 0.93 |
C14A—C26A | 1.397 (2) | C14B—C26B | 1.398 (2) |
C14A—C22A | 1.404 (2) | C14B—C22B | 1.401 (2) |
C14A—C15A | 1.473 (2) | C14B—C15B | 1.478 (2) |
C15A—O27A | 1.2247 (19) | C15B—O27B | 1.2232 (18) |
C15A—C16A | 1.474 (2) | C15B—C16B | 1.477 (2) |
C16A—C17A | 1.391 (2) | C16B—C17B | 1.396 (2) |
C16A—C21A | 1.401 (2) | C16B—C21B | 1.3984 (19) |
C17A—C18A | 1.375 (3) | C17B—C18B | 1.370 (3) |
C17A—H17A | 0.93 | C17B—H17B | 0.93 |
C18A—C19A | 1.379 (3) | C18B—C19B | 1.381 (3) |
C18A—H18A | 0.93 | C18B—H18B | 0.93 |
C19A—C20A | 1.383 (2) | C19B—C20B | 1.386 (2) |
C19A—H19A | 0.93 | C19B—H19B | 0.93 |
C20A—C21A | 1.394 (2) | C20B—C21B | 1.390 (2) |
C20A—H20A | 0.93 | C20B—H20B | 0.93 |
C22A—C23A | 1.399 (2) | C22B—C23B | 1.395 (2) |
C23A—C24A | 1.383 (2) | C23B—C24B | 1.384 (3) |
C23A—H23A | 0.93 | C23B—H23B | 0.93 |
C24A—C25A | 1.377 (3) | C24B—C25B | 1.377 (3) |
C24A—H24A | 0.93 | C24B—H24B | 0.93 |
C25A—C26A | 1.369 (3) | C25B—C26B | 1.372 (3) |
C25A—H25A | 0.93 | C25B—H25B | 0.93 |
C26A—H26A | 0.93 | C26B—H26B | 0.93 |
C29A—H29A | 0.96 | C29B—H29D | 0.96 |
C29A—H29B | 0.96 | C29B—H29E | 0.96 |
C29A—H29C | 0.96 | C29B—H29F | 0.96 |
| | | |
C29A—N1A—C2A | 115.74 (12) | C2B—N1B—C29B | 115.46 (13) |
C29A—N1A—C5A | 114.78 (13) | C2B—N1B—C5B | 108.37 (13) |
C2A—N1A—C5A | 108.02 (11) | C29B—N1B—C5B | 114.30 (14) |
N1A—C2A—C8A | 113.61 (11) | N1B—C2B—C8B | 114.94 (13) |
N1A—C2A—C7A | 113.76 (11) | N1B—C2B—C7B | 115.22 (12) |
C8A—C2A—C7A | 101.23 (10) | C8B—C2B—C7B | 101.17 (11) |
N1A—C2A—C3A | 101.26 (10) | N1B—C2B—C3B | 101.77 (11) |
C8A—C2A—C3A | 117.13 (11) | C8B—C2B—C3B | 116.05 (11) |
C7A—C2A—C3A | 110.38 (11) | C7B—C2B—C3B | 108.07 (12) |
C21A—C3A—C22A | 111.88 (12) | C22B—C3B—C21B | 110.90 (11) |
C21A—C3A—C4A | 110.45 (11) | C22B—C3B—C4B | 115.05 (12) |
C22A—C3A—C4A | 114.37 (12) | C21B—C3B—C4B | 112.01 (12) |
C21A—C3A—C2A | 107.63 (10) | C22B—C3B—C2B | 110.74 (11) |
C22A—C3A—C2A | 111.52 (11) | C21B—C3B—C2B | 107.44 (11) |
C4A—C3A—C2A | 100.23 (11) | C4B—C3B—C2B | 99.97 (11) |
C5A—C4A—C3A | 106.56 (12) | C5B—C4B—C3B | 106.86 (12) |
C5A—C4A—H4A | 110.4 | C5B—C4B—H4C | 110.3 |
C3A—C4A—H4A | 110.4 | C3B—C4B—H4C | 110.3 |
C5A—C4A—H4B | 110.4 | C5B—C4B—H4D | 110.3 |
C3A—C4A—H4B | 110.4 | C3B—C4B—H4D | 110.3 |
H4A—C4A—H4B | 108.6 | H4C—C4B—H4D | 108.6 |
N1A—C5A—C4A | 105.31 (11) | N1B—C5B—C4B | 105.55 (12) |
N1A—C5A—H5A | 110.7 | N1B—C5B—H5C | 110.6 |
C4A—C5A—H5A | 110.7 | C4B—C5B—H5C | 110.6 |
N1A—C5A—H5B | 110.7 | N1B—C5B—H5D | 110.6 |
C4A—C5A—H5B | 110.7 | C4B—C5B—H5D | 110.6 |
H5A—C5A—H5B | 108.8 | H5C—C5B—H5D | 108.8 |
C7A—N6A—C13A | 111.72 (11) | C7B—N6B—C13B | 111.20 (13) |
C7A—N6A—H6A | 124.1 | C7B—N6B—H6B | 124.4 |
C13A—N6A—H6A | 124.1 | C13B—N6B—H6B | 124.4 |
O28A—C7A—N6A | 125.45 (13) | O28B—C7B—N6B | 125.88 (14) |
O28A—C7A—C2A | 126.40 (12) | O28B—C7B—C2B | 126.08 (14) |
N6A—C7A—C2A | 108.12 (11) | N6B—C7B—C2B | 108.04 (12) |
C9A—C8A—C13A | 119.38 (12) | C9B—C8B—C13B | 119.68 (14) |
C9A—C8A—C2A | 131.67 (12) | C9B—C8B—C2B | 131.32 (14) |
C13A—C8A—C2A | 108.77 (11) | C13B—C8B—C2B | 108.97 (13) |
C8A—C9A—C10A | 118.82 (13) | C8B—C9B—C10B | 118.61 (16) |
C8A—C9A—H9A | 120.6 | C8B—C9B—H9B | 120.7 |
C10A—C9A—H9A | 120.6 | C10B—C9B—H9B | 120.7 |
C11A—C10A—C9A | 120.64 (14) | C11B—C10B—C9B | 120.54 (16) |
C11A—C10A—H10A | 119.7 | C11B—C10B—H10B | 119.7 |
C9A—C10A—H10A | 119.7 | C9B—C10B—H10B | 119.7 |
C12A—C11A—C10A | 121.34 (14) | C10B—C11B—C12B | 121.64 (16) |
C12A—C11A—H11A | 119.3 | C10B—C11B—H11B | 119.2 |
C10A—C11A—H11A | 119.3 | C12B—C11B—H11B | 119.2 |
C13A—C12A—C11A | 117.42 (14) | C11B—C12B—C13B | 117.31 (17) |
C13A—C12A—H12A | 121.3 | C11B—C12B—H12B | 121.3 |
C11A—C12A—H12A | 121.3 | C13B—C12B—H12B | 121.3 |
C12A—C13A—C8A | 122.38 (13) | C12B—C13B—C8B | 122.10 (15) |
C12A—C13A—N6A | 127.68 (13) | C12B—C13B—N6B | 128.08 (15) |
C8A—C13A—N6A | 109.79 (11) | C8B—C13B—N6B | 109.79 (13) |
C26A—C14A—C22A | 120.28 (16) | C26B—C14B—C22B | 120.96 (15) |
C26A—C14A—C15A | 118.14 (15) | C26B—C14B—C15B | 118.05 (15) |
C22A—C14A—C15A | 121.53 (13) | C22B—C14B—C15B | 120.80 (14) |
O27A—C15A—C14A | 121.20 (15) | O27B—C15B—C16B | 121.79 (15) |
O27A—C15A—C16A | 122.06 (16) | O27B—C15B—C14B | 122.13 (15) |
C14A—C15A—C16A | 116.63 (13) | C16B—C15B—C14B | 115.89 (13) |
C17A—C16A—C21A | 121.31 (14) | C17B—C16B—C21B | 120.84 (14) |
C17A—C16A—C15A | 118.26 (14) | C17B—C16B—C15B | 118.48 (14) |
C21A—C16A—C15A | 120.40 (14) | C21B—C16B—C15B | 120.66 (13) |
C18A—C17A—C16A | 120.32 (15) | C18B—C17B—C16B | 120.45 (16) |
C18A—C17A—H17A | 119.8 | C18B—C17B—H17B | 119.8 |
C16A—C17A—H17A | 119.8 | C16B—C17B—H17B | 119.8 |
C17A—C18A—C19A | 119.26 (16) | C17B—C18B—C19B | 119.35 (15) |
C17A—C18A—H18A | 120.4 | C17B—C18B—H18B | 120.3 |
C19A—C18A—H18A | 120.4 | C19B—C18B—H18B | 120.3 |
C18A—C19A—C20A | 120.76 (16) | C18B—C19B—C20B | 120.62 (16) |
C18A—C19A—H19A | 119.6 | C18B—C19B—H19B | 119.7 |
C20A—C19A—H19A | 119.6 | C20B—C19B—H19B | 119.7 |
C19A—C20A—C21A | 121.33 (15) | C19B—C20B—C21B | 121.07 (15) |
C19A—C20A—H20A | 119.3 | C19B—C20B—H20B | 119.5 |
C21A—C20A—H20A | 119.3 | C21B—C20B—H20B | 119.5 |
C20A—C21A—C16A | 117.02 (14) | C20B—C21B—C16B | 117.63 (13) |
C20A—C21A—C3A | 121.57 (13) | C20B—C21B—C3B | 122.44 (13) |
C16A—C21A—C3A | 121.26 (12) | C16B—C21B—C3B | 119.83 (12) |
C23A—C22A—C14A | 117.48 (14) | C23B—C22B—C14B | 117.36 (14) |
C23A—C22A—C3A | 122.30 (14) | C23B—C22B—C3B | 123.14 (13) |
C14A—C22A—C3A | 120.17 (13) | C14B—C22B—C3B | 119.43 (13) |
C24A—C23A—C22A | 121.28 (18) | C24B—C23B—C22B | 121.00 (17) |
C24A—C23A—H23A | 119.4 | C24B—C23B—H23B | 119.5 |
C22A—C23A—H23A | 119.4 | C22B—C23B—H23B | 119.5 |
C25A—C24A—C23A | 120.43 (19) | C25B—C24B—C23B | 120.99 (17) |
C25A—C24A—H24A | 119.8 | C25B—C24B—H24B | 119.5 |
C23A—C24A—H24A | 119.8 | C23B—C24B—H24B | 119.5 |
C26A—C25A—C24A | 119.62 (16) | C26B—C25B—C24B | 119.31 (17) |
C26A—C25A—H25A | 120.2 | C26B—C25B—H25B | 120.3 |
C24A—C25A—H25A | 120.2 | C24B—C25B—H25B | 120.3 |
C25A—C26A—C14A | 120.87 (18) | C25B—C26B—C14B | 120.36 (17) |
C25A—C26A—H26A | 119.6 | C25B—C26B—H26B | 119.8 |
C14A—C26A—H26A | 119.6 | C14B—C26B—H26B | 119.8 |
N1A—C29A—H29A | 109.5 | N1B—C29B—H29D | 109.5 |
N1A—C29A—H29B | 109.5 | N1B—C29B—H29E | 109.5 |
H29A—C29A—H29B | 109.5 | H29D—C29B—H29E | 109.5 |
N1A—C29A—H29C | 109.5 | N1B—C29B—H29F | 109.5 |
H29A—C29A—H29C | 109.5 | H29D—C29B—H29F | 109.5 |
H29B—C29A—H29C | 109.5 | H29E—C29B—H29F | 109.5 |
| | | |
C29A—N1A—C2A—C8A | 60.52 (16) | C29B—N1B—C2B—C8B | −63.33 (18) |
C5A—N1A—C2A—C8A | −169.23 (12) | C5B—N1B—C2B—C8B | 167.00 (12) |
C29A—N1A—C2A—C7A | −54.62 (17) | C29B—N1B—C2B—C7B | 53.76 (19) |
C5A—N1A—C2A—C7A | 75.63 (14) | C5B—N1B—C2B—C7B | −75.92 (15) |
C29A—N1A—C2A—C3A | −173.01 (12) | C29B—N1B—C2B—C3B | 170.39 (14) |
C5A—N1A—C2A—C3A | −42.76 (13) | C5B—N1B—C2B—C3B | 40.72 (14) |
N1A—C2A—C3A—C21A | −75.88 (12) | N1B—C2B—C3B—C22B | −160.95 (11) |
C8A—C2A—C3A—C21A | 48.24 (14) | C8B—C2B—C3B—C22B | 73.51 (16) |
C7A—C2A—C3A—C21A | 163.31 (10) | C7B—C2B—C3B—C22B | −39.22 (14) |
N1A—C2A—C3A—C22A | 161.05 (11) | N1B—C2B—C3B—C21B | 77.81 (13) |
C8A—C2A—C3A—C22A | −74.84 (14) | C8B—C2B—C3B—C21B | −47.74 (16) |
C7A—C2A—C3A—C22A | 40.24 (14) | C7B—C2B—C3B—C21B | −160.47 (11) |
N1A—C2A—C3A—C4A | 39.59 (13) | N1B—C2B—C3B—C4B | −39.20 (13) |
C8A—C2A—C3A—C4A | 163.70 (11) | C8B—C2B—C3B—C4B | −164.74 (13) |
C7A—C2A—C3A—C4A | −81.22 (12) | C7B—C2B—C3B—C4B | 82.53 (13) |
C21A—C3A—C4A—C5A | 89.59 (15) | C22B—C3B—C4B—C5B | 143.51 (13) |
C22A—C3A—C4A—C5A | −143.13 (13) | C21B—C3B—C4B—C5B | −88.64 (15) |
C2A—C3A—C4A—C5A | −23.73 (15) | C2B—C3B—C4B—C5B | 24.89 (15) |
C29A—N1A—C5A—C4A | 158.60 (13) | C2B—N1B—C5B—C4B | −25.01 (17) |
C2A—N1A—C5A—C4A | 27.82 (16) | C29B—N1B—C5B—C4B | −155.32 (15) |
C3A—C4A—C5A—N1A | −0.32 (17) | C3B—C4B—C5B—N1B | −2.19 (17) |
C13A—N6A—C7A—O28A | 172.42 (14) | C13B—N6B—C7B—O28B | −172.73 (16) |
C13A—N6A—C7A—C2A | −5.82 (16) | C13B—N6B—C7B—C2B | 7.13 (17) |
N1A—C2A—C7A—O28A | −50.0 (2) | N1B—C2B—C7B—O28B | 46.2 (2) |
C8A—C2A—C7A—O28A | −172.28 (14) | C8B—C2B—C7B—O28B | 170.87 (16) |
C3A—C2A—C7A—O28A | 63.00 (18) | C3B—C2B—C7B—O28B | −66.76 (19) |
N1A—C2A—C7A—N6A | 128.20 (13) | N1B—C2B—C7B—N6B | −133.61 (14) |
C8A—C2A—C7A—N6A | 5.95 (14) | C8B—C2B—C7B—N6B | −8.99 (16) |
C3A—C2A—C7A—N6A | −118.78 (12) | C3B—C2B—C7B—N6B | 113.38 (13) |
N1A—C2A—C8A—C9A | 48.44 (19) | N1B—C2B—C8B—C9B | −45.7 (2) |
C7A—C2A—C8A—C9A | 170.80 (14) | C7B—C2B—C8B—C9B | −170.48 (16) |
C3A—C2A—C8A—C9A | −69.16 (18) | C3B—C2B—C8B—C9B | 72.9 (2) |
N1A—C2A—C8A—C13A | −126.44 (12) | N1B—C2B—C8B—C13B | 132.65 (13) |
C7A—C2A—C8A—C13A | −4.09 (13) | C7B—C2B—C8B—C13B | 7.83 (15) |
C3A—C2A—C8A—C13A | 115.95 (12) | C3B—C2B—C8B—C13B | −108.81 (14) |
C13A—C8A—C9A—C10A | −1.48 (19) | C13B—C8B—C9B—C10B | 3.2 (2) |
C2A—C8A—C9A—C10A | −175.92 (13) | C2B—C8B—C9B—C10B | −178.60 (16) |
C8A—C9A—C10A—C11A | 0.6 (2) | C8B—C9B—C10B—C11B | −0.4 (3) |
C9A—C10A—C11A—C12A | 0.5 (2) | C9B—C10B—C11B—C12B | −1.9 (3) |
C10A—C11A—C12A—C13A | −0.8 (2) | C10B—C11B—C12B—C13B | 1.1 (3) |
C11A—C12A—C13A—C8A | −0.1 (2) | C11B—C12B—C13B—C8B | 1.8 (3) |
C11A—C12A—C13A—N6A | 174.95 (14) | C11B—C12B—C13B—N6B | −176.19 (18) |
C9A—C8A—C13A—C12A | 1.2 (2) | C9B—C8B—C13B—C12B | −4.1 (2) |
C2A—C8A—C13A—C12A | 176.84 (13) | C2B—C8B—C13B—C12B | 177.40 (15) |
C9A—C8A—C13A—N6A | −174.58 (12) | C9B—C8B—C13B—N6B | 174.28 (14) |
C2A—C8A—C13A—N6A | 1.03 (15) | C2B—C8B—C13B—N6B | −4.26 (17) |
C7A—N6A—C13A—C12A | −172.35 (14) | C7B—N6B—C13B—C12B | 176.22 (18) |
C7A—N6A—C13A—C8A | 3.17 (16) | C7B—N6B—C13B—C8B | −1.98 (19) |
C26A—C14A—C15A—O27A | 17.8 (2) | C26B—C14B—C15B—O27B | −19.6 (2) |
C22A—C14A—C15A—O27A | −164.91 (16) | C22B—C14B—C15B—O27B | 165.42 (16) |
C26A—C14A—C15A—C16A | −158.54 (14) | C26B—C14B—C15B—C16B | 155.39 (14) |
C22A—C14A—C15A—C16A | 18.8 (2) | C22B—C14B—C15B—C16B | −19.6 (2) |
O27A—C15A—C16A—C17A | −14.8 (2) | O27B—C15B—C16B—C17B | 17.8 (2) |
C14A—C15A—C16A—C17A | 161.44 (14) | C14B—C15B—C16B—C17B | −157.27 (14) |
O27A—C15A—C16A—C21A | 167.33 (16) | O27B—C15B—C16B—C21B | −163.85 (16) |
C14A—C15A—C16A—C21A | −16.4 (2) | C14B—C15B—C16B—C21B | 21.1 (2) |
C21A—C16A—C17A—C18A | 0.1 (2) | C21B—C16B—C17B—C18B | −1.5 (2) |
C15A—C16A—C17A—C18A | −177.78 (15) | C15B—C16B—C17B—C18B | 176.89 (15) |
C16A—C17A—C18A—C19A | 0.7 (3) | C16B—C17B—C18B—C19B | 0.4 (3) |
C17A—C18A—C19A—C20A | −0.6 (3) | C17B—C18B—C19B—C20B | 1.4 (3) |
C18A—C19A—C20A—C21A | −0.2 (3) | C18B—C19B—C20B—C21B | −2.2 (3) |
C19A—C20A—C21A—C16A | 0.9 (2) | C19B—C20B—C21B—C16B | 1.1 (2) |
C19A—C20A—C21A—C3A | −174.71 (14) | C19B—C20B—C21B—C3B | 177.43 (14) |
C17A—C16A—C21A—C20A | −0.8 (2) | C17B—C16B—C21B—C20B | 0.7 (2) |
C15A—C16A—C21A—C20A | 176.97 (13) | C15B—C16B—C21B—C20B | −177.62 (14) |
C17A—C16A—C21A—C3A | 174.78 (13) | C17B—C16B—C21B—C3B | −175.72 (13) |
C15A—C16A—C21A—C3A | −7.4 (2) | C15B—C16B—C21B—C3B | 5.9 (2) |
C22A—C3A—C21A—C20A | −157.20 (13) | C22B—C3B—C21B—C20B | 151.31 (13) |
C4A—C3A—C21A—C20A | −28.56 (18) | C4B—C3B—C21B—C20B | 21.28 (19) |
C2A—C3A—C21A—C20A | 79.95 (15) | C2B—C3B—C21B—C20B | −87.54 (15) |
C22A—C3A—C21A—C16A | 27.40 (17) | C22B—C3B—C21B—C16B | −32.41 (17) |
C4A—C3A—C21A—C16A | 156.04 (13) | C4B—C3B—C21B—C16B | −162.43 (13) |
C2A—C3A—C21A—C16A | −95.46 (14) | C2B—C3B—C21B—C16B | 88.74 (15) |
C26A—C14A—C22A—C23A | −2.3 (2) | C26B—C14B—C22B—C23B | −0.8 (2) |
C15A—C14A—C22A—C23A | −179.56 (14) | C15B—C14B—C22B—C23B | 174.07 (14) |
C26A—C14A—C22A—C3A | −179.86 (14) | C26B—C14B—C22B—C3B | 176.25 (13) |
C15A—C14A—C22A—C3A | 2.9 (2) | C15B—C14B—C22B—C3B | −8.9 (2) |
C21A—C3A—C22A—C23A | 157.65 (13) | C21B—C3B—C22B—C23B | −149.31 (13) |
C4A—C3A—C22A—C23A | 31.1 (2) | C4B—C3B—C22B—C23B | −20.91 (19) |
C2A—C3A—C22A—C23A | −81.73 (16) | C2B—C3B—C22B—C23B | 91.50 (16) |
C21A—C3A—C22A—C14A | −24.89 (17) | C21B—C3B—C22B—C14B | 33.86 (17) |
C4A—C3A—C22A—C14A | −151.43 (14) | C4B—C3B—C22B—C14B | 162.27 (13) |
C2A—C3A—C22A—C14A | 95.73 (15) | C2B—C3B—C22B—C14B | −85.33 (15) |
C14A—C22A—C23A—C24A | 0.8 (2) | C14B—C22B—C23B—C24B | −0.5 (2) |
C3A—C22A—C23A—C24A | 178.31 (15) | C3B—C22B—C23B—C24B | −177.37 (14) |
C22A—C23A—C24A—C25A | 1.2 (3) | C22B—C23B—C24B—C25B | 1.3 (3) |
C23A—C24A—C25A—C26A | −1.7 (3) | C23B—C24B—C25B—C26B | −0.9 (3) |
C24A—C25A—C26A—C14A | 0.2 (3) | C24B—C25B—C26B—C14B | −0.3 (3) |
C22A—C14A—C26A—C25A | 1.9 (2) | C22B—C14B—C26B—C25B | 1.2 (2) |
C15A—C14A—C26A—C25A | 179.23 (16) | C15B—C14B—C26B—C25B | −173.78 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6A—H6A···O28B | 0.86 | 2.00 | 2.832 (2) | 161 |
N6B—H6B···O28A | 0.86 | 2.08 | 2.883 (2) | 155 |
C23A—H23A···O28A | 0.93 | 2.49 | 3.000 (2) | 115 |
C23B—H23B···O28B | 0.93 | 2.74 | 3.093 (2) | 104 |
C20A—H20A···O27Ai | 0.93 | 2.85 | 3.641 (2) | 144 |
C5A—H5B···O27Ai | 0.97 | 2.95 | 3.872 (2) | 159 |
C11A—H11A···O27Aii | 0.93 | 2.74 | 3.461 (2) | 135 |
C12A—H12A···O27Biii | 0.93 | 2.88 | 3.702 (2) | 149 |
C18B—H18B···O28Aiv | 0.93 | 2.95 | 3.643 (2) | 133 |
C19B—H19B···O27Bv | 0.93 | 2.56 | 3.403 (2) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z+1/2; (v) x+1, y, z. |