The pyrrolidine ring of the title compound, C
30H
24N
2O
5, adopts a half-chair conformation. The structure is stabilized by C—H
O intramolecular interactions and the packing of the molecules is stabilized by C—H
O and N—H
O intermolecular interactions.
Supporting information
CCDC reference: 227007
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.139
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without
a literature citation. This should be contained in the
_exptl_absorpt_process_details field.
Absorption correction given as multi-scan
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.99
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 5528
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 5828
Completeness (_total/calc) 94.85%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C33
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
2'-(
p-Methoxybenzoyl)-1',2,2',3,5',6',7',7a'-octahydro-1
H-indan-2-spiro-3'-
(3'
H-pyrrolizine)-1'-spiro-3''-1
H-indoline-1,2'',3-trione
top
Crystal data top
C30H24N2O5 | F(000) = 1032 |
Mr = 492.51 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3592 reflections |
a = 11.4931 (8) Å | θ = 2.3–26° |
b = 13.6374 (9) Å | µ = 0.09 mm−1 |
c = 15.5377 (10) Å | T = 293 K |
β = 96.351 (1)° | Prisms, yellow |
V = 2420.4 (3) Å3 | 0.23 × 0.20 × 0.17 mm |
Z = 4 | |
Data collection top
CCD Area Detector diffractometer | 5528 independent reflections |
Radiation source: fine-focus sealed tube | 3764 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan | h = −14→14 |
Tmin = 0.979, Tmax = 0.984 | k = −17→17 |
14548 measured reflections | l = −20→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0798P)2 + 0.041P] where P = (Fo2 + 2Fc2)/3 |
5528 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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 | |
N1 | 0.34651 (13) | 0.45085 (11) | −0.02912 (10) | 0.0450 (4) | |
H1 | 0.3818 | 0.5029 | −0.0438 | 0.054* | |
C2 | 0.39982 (15) | 0.37685 (12) | 0.01661 (10) | 0.0354 (4) | |
O3 | 0.50239 (10) | 0.37660 (9) | 0.04859 (8) | 0.0421 (3) | |
C4 | 0.31036 (14) | 0.29370 (12) | 0.02195 (10) | 0.0343 (4) | |
C5 | 0.19908 (14) | 0.34145 (13) | −0.01848 (10) | 0.0368 (4) | |
C6 | 0.08488 (16) | 0.30866 (14) | −0.03079 (12) | 0.0468 (5) | |
H6 | 0.0652 | 0.2473 | −0.0107 | 0.056* | |
C7 | −0.00001 (17) | 0.36872 (16) | −0.07364 (14) | 0.0588 (6) | |
H7 | −0.0774 | 0.3477 | −0.0817 | 0.071* | |
C8 | 0.02888 (19) | 0.45914 (17) | −0.10443 (14) | 0.0636 (6) | |
H8 | −0.0293 | 0.4984 | −0.1330 | 0.076* | |
C9 | 0.14330 (19) | 0.49249 (16) | −0.09349 (13) | 0.0584 (5) | |
H9 | 0.1631 | 0.5532 | −0.1149 | 0.070* | |
C10 | 0.22643 (16) | 0.43324 (13) | −0.05017 (11) | 0.0425 (4) | |
C11 | 0.31411 (14) | 0.25104 (11) | 0.11563 (10) | 0.0316 (4) | |
H11 | 0.3877 | 0.2742 | 0.1469 | 0.038* | |
C12 | 0.21902 (14) | 0.27534 (12) | 0.17327 (11) | 0.0359 (4) | |
O13 | 0.15552 (13) | 0.20928 (10) | 0.19249 (10) | 0.0604 (4) | |
C14 | 0.21215 (13) | 0.37325 (11) | 0.21284 (10) | 0.0332 (4) | |
C15 | 0.28086 (15) | 0.45256 (13) | 0.19315 (12) | 0.0421 (4) | |
H15 | 0.3320 | 0.4455 | 0.1512 | 0.051* | |
C16 | 0.27441 (16) | 0.54110 (13) | 0.23467 (12) | 0.0457 (4) | |
H16 | 0.3194 | 0.5937 | 0.2196 | 0.055* | |
C17 | 0.20125 (14) | 0.55203 (12) | 0.29868 (11) | 0.0380 (4) | |
C18 | 0.13261 (16) | 0.47423 (13) | 0.31983 (11) | 0.0429 (4) | |
H18 | 0.0831 | 0.4811 | 0.3629 | 0.051* | |
C19 | 0.13832 (15) | 0.38662 (13) | 0.27653 (11) | 0.0411 (4) | |
H19 | 0.0912 | 0.3348 | 0.2905 | 0.049* | |
C20 | 0.32788 (14) | 0.13979 (11) | 0.10581 (10) | 0.0329 (4) | |
C21 | 0.21731 (14) | 0.07491 (12) | 0.08790 (11) | 0.0360 (4) | |
O22 | 0.13732 (11) | 0.08654 (9) | 0.03124 (8) | 0.0484 (3) | |
C23 | 0.23388 (15) | −0.01185 (12) | 0.14532 (11) | 0.0376 (4) | |
C24 | 0.16536 (17) | −0.09573 (13) | 0.14597 (12) | 0.0469 (5) | |
H24 | 0.0973 | −0.1028 | 0.1081 | 0.056* | |
C25 | 0.2021 (2) | −0.16837 (14) | 0.20501 (14) | 0.0564 (5) | |
H25 | 0.1576 | −0.2252 | 0.2070 | 0.068* | |
C26 | 0.3031 (2) | −0.15828 (15) | 0.26099 (14) | 0.0583 (6) | |
H26 | 0.3263 | −0.2090 | 0.2991 | 0.070* | |
C27 | 0.37036 (18) | −0.07499 (14) | 0.26171 (12) | 0.0498 (5) | |
H27 | 0.4376 | −0.0679 | 0.3004 | 0.060* | |
C28 | 0.33427 (15) | −0.00196 (12) | 0.20270 (11) | 0.0381 (4) | |
C29 | 0.39017 (15) | 0.09307 (12) | 0.18893 (11) | 0.0370 (4) | |
O30 | 0.46823 (11) | 0.13134 (9) | 0.23561 (8) | 0.0508 (3) | |
N31 | 0.39098 (12) | 0.12556 (10) | 0.03008 (9) | 0.0372 (3) | |
C32 | 0.51955 (15) | 0.13827 (14) | 0.04253 (12) | 0.0462 (5) | |
H32A | 0.5585 | 0.0773 | 0.0605 | 0.055* | |
H32B | 0.5421 | 0.1884 | 0.0854 | 0.055* | |
C33 | 0.54875 (19) | 0.1692 (2) | −0.04613 (15) | 0.0671 (6) | |
H33A | 0.5759 | 0.1134 | −0.0770 | 0.081* | |
H33B | 0.6098 | 0.2187 | −0.0408 | 0.081* | |
C34 | 0.43745 (18) | 0.21049 (15) | −0.09419 (12) | 0.0519 (5) | |
H34A | 0.4156 | 0.1740 | −0.1471 | 0.062* | |
H34B | 0.4479 | 0.2788 | −0.1088 | 0.062* | |
C35 | 0.34382 (15) | 0.19991 (12) | −0.03212 (11) | 0.0386 (4) | |
H35 | 0.2723 | 0.1742 | −0.0645 | 0.046* | |
O36 | 0.20315 (12) | 0.64125 (9) | 0.33735 (9) | 0.0537 (4) | |
C37 | 0.1288 (2) | 0.65794 (18) | 0.40243 (16) | 0.0761 (7) | |
H37A | 0.1393 | 0.7238 | 0.4237 | 0.114* | |
H37B | 0.1477 | 0.6126 | 0.4492 | 0.114* | |
H37C | 0.0488 | 0.6487 | 0.3787 | 0.114* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0444 (9) | 0.0412 (8) | 0.0488 (9) | −0.0065 (7) | 0.0024 (7) | 0.0145 (7) |
C2 | 0.0377 (9) | 0.0396 (9) | 0.0291 (9) | −0.0039 (7) | 0.0046 (7) | 0.0014 (7) |
O3 | 0.0357 (7) | 0.0460 (7) | 0.0434 (7) | −0.0077 (5) | −0.0009 (5) | 0.0029 (5) |
C4 | 0.0328 (8) | 0.0374 (9) | 0.0320 (9) | −0.0033 (7) | 0.0000 (7) | 0.0012 (7) |
C5 | 0.0350 (9) | 0.0433 (10) | 0.0310 (9) | −0.0006 (7) | −0.0009 (7) | 0.0035 (7) |
C6 | 0.0398 (10) | 0.0505 (11) | 0.0480 (11) | −0.0027 (8) | −0.0045 (8) | 0.0040 (8) |
C7 | 0.0387 (11) | 0.0724 (15) | 0.0617 (14) | 0.0015 (10) | −0.0110 (9) | 0.0063 (11) |
C8 | 0.0519 (12) | 0.0739 (15) | 0.0613 (14) | 0.0150 (11) | −0.0104 (10) | 0.0178 (11) |
C9 | 0.0603 (13) | 0.0548 (12) | 0.0581 (13) | 0.0057 (10) | −0.0020 (10) | 0.0231 (10) |
C10 | 0.0427 (10) | 0.0480 (10) | 0.0363 (10) | −0.0004 (8) | 0.0019 (8) | 0.0090 (8) |
C11 | 0.0317 (8) | 0.0321 (8) | 0.0301 (8) | −0.0010 (7) | −0.0008 (6) | 0.0020 (6) |
C12 | 0.0354 (9) | 0.0375 (9) | 0.0344 (9) | −0.0012 (7) | 0.0025 (7) | 0.0039 (7) |
O13 | 0.0691 (9) | 0.0436 (8) | 0.0750 (10) | −0.0146 (7) | 0.0365 (8) | −0.0077 (7) |
C14 | 0.0299 (8) | 0.0361 (9) | 0.0328 (9) | 0.0031 (7) | 0.0001 (7) | 0.0030 (7) |
C15 | 0.0386 (9) | 0.0427 (10) | 0.0475 (11) | −0.0019 (8) | 0.0163 (8) | −0.0030 (8) |
C16 | 0.0446 (10) | 0.0382 (10) | 0.0566 (12) | −0.0074 (8) | 0.0163 (9) | −0.0021 (8) |
C17 | 0.0374 (9) | 0.0363 (9) | 0.0400 (10) | 0.0033 (7) | 0.0032 (7) | −0.0007 (7) |
C18 | 0.0459 (10) | 0.0444 (10) | 0.0409 (10) | 0.0010 (8) | 0.0162 (8) | 0.0010 (8) |
C19 | 0.0439 (10) | 0.0399 (10) | 0.0410 (10) | −0.0033 (8) | 0.0113 (8) | 0.0050 (7) |
C20 | 0.0340 (8) | 0.0326 (8) | 0.0314 (9) | −0.0004 (7) | 0.0004 (7) | −0.0013 (6) |
C21 | 0.0360 (9) | 0.0350 (9) | 0.0373 (9) | 0.0016 (7) | 0.0053 (7) | −0.0048 (7) |
O22 | 0.0438 (7) | 0.0473 (7) | 0.0508 (8) | −0.0050 (6) | −0.0092 (6) | 0.0029 (6) |
C23 | 0.0427 (9) | 0.0358 (9) | 0.0359 (9) | 0.0025 (7) | 0.0116 (7) | −0.0013 (7) |
C24 | 0.0497 (11) | 0.0401 (10) | 0.0527 (12) | −0.0025 (8) | 0.0143 (9) | −0.0027 (8) |
C25 | 0.0717 (14) | 0.0383 (10) | 0.0625 (14) | −0.0058 (10) | 0.0217 (11) | 0.0047 (9) |
C26 | 0.0769 (15) | 0.0450 (11) | 0.0550 (13) | 0.0085 (10) | 0.0155 (11) | 0.0150 (9) |
C27 | 0.0611 (12) | 0.0469 (11) | 0.0414 (11) | 0.0073 (9) | 0.0056 (9) | 0.0085 (8) |
C28 | 0.0448 (10) | 0.0374 (9) | 0.0328 (9) | 0.0052 (7) | 0.0076 (7) | −0.0001 (7) |
C29 | 0.0388 (9) | 0.0385 (9) | 0.0336 (9) | 0.0075 (7) | 0.0029 (7) | −0.0019 (7) |
O30 | 0.0517 (8) | 0.0494 (8) | 0.0468 (8) | −0.0001 (6) | −0.0141 (6) | −0.0031 (6) |
N31 | 0.0382 (8) | 0.0392 (8) | 0.0340 (8) | 0.0025 (6) | 0.0034 (6) | −0.0030 (6) |
C32 | 0.0373 (10) | 0.0506 (11) | 0.0509 (12) | 0.0064 (8) | 0.0062 (8) | −0.0044 (8) |
C33 | 0.0545 (13) | 0.0885 (17) | 0.0619 (14) | 0.0093 (12) | 0.0224 (11) | 0.0015 (12) |
C34 | 0.0619 (13) | 0.0592 (12) | 0.0365 (10) | −0.0023 (10) | 0.0133 (9) | −0.0058 (9) |
C35 | 0.0425 (10) | 0.0408 (10) | 0.0315 (9) | −0.0030 (7) | −0.0003 (7) | −0.0020 (7) |
O36 | 0.0604 (9) | 0.0410 (7) | 0.0630 (9) | −0.0026 (6) | 0.0217 (7) | −0.0120 (6) |
C37 | 0.0943 (19) | 0.0598 (14) | 0.0815 (17) | 0.0012 (13) | 0.0424 (15) | −0.0217 (12) |
Geometric parameters (Å, º) top
N1—C2 | 1.342 (2) | C20—N31 | 1.462 (2) |
N1—C10 | 1.403 (2) | C20—C29 | 1.543 (2) |
N1—H1 | 0.8600 | C20—C21 | 1.548 (2) |
C2—O3 | 1.228 (2) | C21—O22 | 1.211 (2) |
C2—C4 | 1.539 (2) | C21—C23 | 1.481 (2) |
C4—C5 | 1.509 (2) | C23—C28 | 1.385 (2) |
C4—C11 | 1.564 (2) | C23—C24 | 1.389 (2) |
C4—C35 | 1.600 (2) | C24—C25 | 1.384 (3) |
C5—C6 | 1.380 (2) | C24—H24 | 0.9300 |
C5—C10 | 1.394 (2) | C25—C26 | 1.379 (3) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—C6 | 1.386 (3) | C26—C27 | 1.373 (3) |
C7—H7 | 0.9300 | C26—H26 | 0.9300 |
C8—C7 | 1.377 (3) | C27—C28 | 1.386 (2) |
C8—H8 | 0.9300 | C27—H27 | 0.9300 |
C9—C8 | 1.384 (3) | C28—C29 | 1.473 (2) |
C9—H9 | 0.9300 | C29—O30 | 1.208 (2) |
C10—C9 | 1.370 (3) | N31—C35 | 1.463 (2) |
C11—C12 | 1.524 (2) | N31—C32 | 1.479 (2) |
C11—C20 | 1.535 (2) | C32—C33 | 1.514 (3) |
C11—H11 | 0.9800 | C32—H32A | 0.9700 |
C12—O13 | 1.217 (2) | C32—H32B | 0.9700 |
C12—C14 | 1.476 (2) | C33—C34 | 1.516 (3) |
C14—C19 | 1.385 (2) | C33—H33A | 0.9700 |
C14—C15 | 1.393 (2) | C33—H33B | 0.9700 |
C15—C16 | 1.375 (2) | C34—C35 | 1.529 (2) |
C15—H15 | 0.9300 | C34—H34A | 0.9700 |
C16—C17 | 1.380 (2) | C34—H34B | 0.9700 |
C16—H16 | 0.9300 | C35—H35 | 0.9800 |
C17—O36 | 1.356 (2) | O36—C37 | 1.413 (2) |
C17—C18 | 1.383 (2) | C37—H37A | 0.9600 |
C18—C19 | 1.376 (2) | C37—H37B | 0.9600 |
C18—H18 | 0.9300 | C37—H37C | 0.9600 |
C19—H19 | 0.9300 | | |
| | | |
C2—N1—C10 | 112.0 (1) | C11—C20—C21 | 119.42 (13) |
C2—N1—H1 | 124.0 | C29—C20—C21 | 102.12 (13) |
C10—N1—H1 | 124.0 | O22—C21—C23 | 125.4 (2) |
O3—C2—N1 | 125.31 (15) | O22—C21—C20 | 126.7 (2) |
O3—C2—C4 | 126.4 (2) | C23—C21—C20 | 107.45 (14) |
N1—C2—C4 | 108.3 (1) | C28—C23—C24 | 120.54 (16) |
C5—C4—C2 | 101.55 (13) | C28—C23—C21 | 110.64 (15) |
C5—C4—C11 | 118.88 (13) | C24—C23—C21 | 128.81 (17) |
C2—C4—C11 | 112.00 (13) | C25—C24—C23 | 117.56 (19) |
C5—C4—C35 | 111.60 (13) | C25—C24—H24 | 121.2 |
C2—C4—C35 | 111.09 (13) | C23—C24—H24 | 121.2 |
C11—C4—C35 | 101.99 (12) | C26—C25—C24 | 121.36 (19) |
C6—C5—C10 | 119.36 (16) | C26—C25—H25 | 119.3 |
C6—C5—C4 | 131.87 (16) | C24—C25—H25 | 119.3 |
C10—C5—C4 | 108.71 (15) | C27—C26—C25 | 121.45 (19) |
C5—C6—C7 | 118.89 (18) | C27—C26—H26 | 119.3 |
C5—C6—H6 | 120.6 | C25—C26—H26 | 119.3 |
C7—C6—H6 | 120.6 | C26—C27—C28 | 117.53 (19) |
C8—C7—C6 | 120.81 (19) | C26—C27—H27 | 121.2 |
C8—C7—H7 | 119.6 | C28—C27—H27 | 121.2 |
C6—C7—H7 | 119.6 | C23—C28—C27 | 121.54 (17) |
C7—C8—C9 | 120.93 (18) | C23—C28—C29 | 109.76 (14) |
C7—C8—H8 | 119.5 | C27—C28—C29 | 128.70 (17) |
C9—C8—H8 | 119.5 | O30—C29—C28 | 126.9 (2) |
C10—C9—C8 | 117.91 (19) | O30—C29—C20 | 124.7 (2) |
C10—C9—H9 | 121.0 | C28—C29—C20 | 108.39 (14) |
C8—C9—H9 | 121.0 | C20—N31—C35 | 105.0 (1) |
C9—C10—C5 | 122.08 (18) | C20—N31—C32 | 117.2 (1) |
C9—C10—N1 | 128.9 (2) | C35—N31—C32 | 107.27 (13) |
C5—C10—N1 | 109.01 (15) | N31—C32—C33 | 103.5 (2) |
C12—C11—C20 | 111.22 (13) | N31—C32—H32A | 111.1 |
C12—C11—C4 | 121.22 (13) | C33—C32—H32A | 111.1 |
C20—C11—C4 | 105.53 (12) | N31—C32—H32B | 111.1 |
C12—C11—H11 | 105.9 | C33—C32—H32B | 111.1 |
C20—C11—H11 | 105.9 | H32A—C32—H32B | 109.0 |
C4—C11—H11 | 105.9 | C32—C33—C34 | 106.96 (15) |
O13—C12—C14 | 120.4 (2) | C32—C33—H33A | 110.3 |
O13—C12—C11 | 118.1 (2) | C34—C33—H33A | 110.3 |
C14—C12—C11 | 121.09 (14) | C32—C33—H33B | 110.3 |
C19—C14—C15 | 117.50 (15) | C34—C33—H33B | 110.3 |
C19—C14—C12 | 118.81 (15) | H33A—C33—H33B | 108.6 |
C15—C14—C12 | 123.59 (15) | C33—C34—C35 | 105.58 (16) |
C16—C15—C14 | 121.17 (16) | C33—C34—H34A | 110.6 |
C16—C15—H15 | 119.4 | C35—C34—H34A | 110.6 |
C14—C15—H15 | 119.4 | C33—C34—H34B | 110.6 |
C15—C16—C17 | 120.13 (16) | C35—C34—H34B | 110.6 |
C15—C16—H16 | 119.9 | H34A—C34—H34B | 108.8 |
C17—C16—H16 | 119.9 | N31—C35—C34 | 104.3 (1) |
O36—C17—C16 | 115.8 (2) | N31—C35—C4 | 107.5 (1) |
O36—C17—C18 | 124.4 (2) | C34—C35—C4 | 118.84 (14) |
C16—C17—C18 | 119.84 (16) | N31—C35—H35 | 108.6 |
C19—C18—C17 | 119.36 (16) | C34—C35—H35 | 108.6 |
C19—C18—H18 | 120.3 | C4—C35—H35 | 108.6 |
C17—C18—H18 | 120.3 | C17—O36—C37 | 118.7 (2) |
C18—C19—C14 | 121.98 (16) | O36—C37—H37A | 109.5 |
C18—C19—H19 | 119.0 | O36—C37—H37B | 109.5 |
C14—C19—H19 | 119.0 | H37A—C37—H37B | 109.5 |
N31—C20—C11 | 106.09 (13) | O36—C37—H37C | 109.5 |
N31—C20—C29 | 113.2 (1) | H37A—C37—H37C | 109.5 |
C11—C20—C29 | 111.61 (13) | H37B—C37—H37C | 109.5 |
N31—C20—C21 | 104.5 (1) | | |
| | | |
C10—N1—C2—O3 | −174.39 (16) | C4—C11—C20—C21 | −88.38 (16) |
C10—N1—C2—C4 | 5.41 (19) | N31—C20—C21—O22 | −66.2 (2) |
O3—C2—C4—C5 | 173.03 (16) | C11—C20—C21—O22 | 52.1 (2) |
N1—C2—C4—C5 | −6.76 (17) | C29—C20—C21—O22 | 175.68 (16) |
O3—C2—C4—C11 | 45.1 (2) | N31—C20—C21—C23 | 106.45 (14) |
N1—C2—C4—C11 | −134.66 (14) | C11—C20—C21—C23 | −135.25 (14) |
O3—C2—C4—C35 | −68.2 (2) | C29—C20—C21—C23 | −11.64 (16) |
N1—C2—C4—C35 | 112.02 (15) | O22—C21—C23—C28 | 179.77 (16) |
C2—C4—C5—C6 | −177.01 (18) | C20—C21—C23—C28 | 6.97 (18) |
C11—C4—C5—C6 | −53.7 (3) | O22—C21—C23—C24 | 1.0 (3) |
C35—C4—C5—C6 | 64.6 (2) | C20—C21—C23—C24 | −171.84 (17) |
C2—C4—C5—C10 | 5.87 (18) | C28—C23—C24—C25 | −0.7 (3) |
C11—C4—C5—C10 | 129.18 (16) | C21—C23—C24—C25 | 178.01 (17) |
C35—C4—C5—C10 | −112.55 (16) | C23—C24—C25—C26 | −0.3 (3) |
C6—C5—C10—C9 | −0.1 (3) | C24—C25—C26—C27 | 1.3 (3) |
C4—C5—C10—C9 | 177.49 (18) | C25—C26—C27—C28 | −1.3 (3) |
C6—C5—C10—N1 | 179.31 (16) | C24—C23—C28—C27 | 0.6 (3) |
C4—C5—C10—N1 | −3.1 (2) | C21—C23—C28—C27 | −178.28 (15) |
C2—N1—C10—C9 | 177.8 (2) | C24—C23—C28—C29 | −179.77 (15) |
C2—N1—C10—C5 | −1.5 (2) | C21—C23—C28—C29 | 1.31 (19) |
C5—C10—C9—C8 | 0.8 (3) | C26—C27—C28—C23 | 0.4 (3) |
N1—C10—C9—C8 | −178.4 (2) | C26—C27—C28—C29 | −179.13 (18) |
C10—C9—C8—C7 | −0.8 (3) | C23—C28—C29—O30 | 168.03 (17) |
C9—C8—C7—C6 | 0.0 (4) | C27—C28—C29—O30 | −12.4 (3) |
C10—C5—C6—C7 | −0.7 (3) | C23—C28—C29—C20 | −9.14 (18) |
C4—C5—C6—C7 | −177.61 (18) | C27—C28—C29—C20 | 170.42 (17) |
C8—C7—C6—C5 | 0.8 (3) | N31—C20—C29—O30 | 83.6 (2) |
C5—C4—C11—C12 | −13.1 (2) | C11—C20—C29—O30 | −36.0 (2) |
C2—C4—C11—C12 | 104.92 (16) | C21—C20—C29—O30 | −164.72 (16) |
C35—C4—C11—C12 | −136.24 (15) | N31—C20—C29—C28 | −99.18 (15) |
C5—C4—C11—C20 | 114.35 (15) | C11—C20—C29—C28 | 141.23 (13) |
C2—C4—C11—C20 | −127.66 (14) | C21—C20—C29—C28 | 12.52 (16) |
C35—C4—C11—C20 | −8.81 (15) | C11—C20—N31—C35 | −38.52 (15) |
C20—C11—C12—O13 | −11.1 (2) | C29—C20—N31—C35 | −161.22 (13) |
C4—C11—C12—O13 | 113.75 (18) | C21—C20—N31—C35 | 88.52 (14) |
C20—C11—C12—C14 | 162.14 (14) | C11—C20—N31—C32 | 80.38 (17) |
C4—C11—C12—C14 | −73.0 (2) | C29—C20—N31—C32 | −42.32 (19) |
O13—C12—C14—C19 | 4.5 (2) | C21—C20—N31—C32 | −152.58 (14) |
C11—C12—C14—C19 | −168.55 (15) | C20—N31—C32—C33 | −152.71 (16) |
O13—C12—C14—C15 | −179.13 (17) | C35—N31—C32—C33 | −35.03 (19) |
C11—C12—C14—C15 | 7.8 (2) | N31—C32—C33—C34 | 21.6 (2) |
C19—C14—C15—C16 | −0.8 (3) | C32—C33—C34—C35 | −1.4 (2) |
C12—C14—C15—C16 | −177.21 (16) | C20—N31—C35—C34 | 159.65 (13) |
C14—C15—C16—C17 | 1.7 (3) | C32—N31—C35—C34 | 34.30 (17) |
C15—C16—C17—O36 | 178.37 (16) | C20—N31—C35—C4 | 32.63 (16) |
C15—C16—C17—C18 | −1.3 (3) | C32—N31—C35—C4 | −92.72 (15) |
O36—C17—C18—C19 | −179.61 (16) | C33—C34—C35—N31 | −19.6 (2) |
C16—C17—C18—C19 | 0.0 (3) | C33—C34—C35—C4 | 100.03 (19) |
C17—C18—C19—C14 | 0.9 (3) | C5—C4—C35—N31 | −141.98 (14) |
C15—C14—C19—C18 | −0.5 (3) | C2—C4—C35—N31 | 105.47 (15) |
C12—C14—C19—C18 | 176.09 (16) | C11—C4—C35—N31 | −14.02 (16) |
C12—C11—C20—N31 | 162.32 (13) | C5—C4—C35—C34 | 100.06 (18) |
C4—C11—C20—N31 | 29.09 (15) | C2—C4—C35—C34 | −12.5 (2) |
C12—C11—C20—C29 | −74.00 (17) | C11—C4—C35—C34 | −131.98 (16) |
C4—C11—C20—C29 | 152.76 (13) | C16—C17—O36—C37 | 178.91 (19) |
C12—C11—C20—C21 | 44.86 (19) | C18—C17—O36—C37 | −1.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.12 | 2.960 (2) | 165 |
C6—H6···O22 | 0.93 | 2.41 | 3.215 (2) | 145 |
C11—H11···O3 | 0.98 | 2.54 | 3.033 (2) | 111 |
C11—H11···O30 | 0.98 | 2.50 | 2.924 (2) | 106 |
C16—H16···O30 | 0.93 | 2.52 | 3.190 (2) | 130 |
C26—H26···O36 | 0.93 | 2.59 | 3.241 (2) | 127 |
C27—H27···O3 | 0.93 | 2.49 | 3.211 (2) | 134 |
C35—H35···O22 | 0.98 | 2.56 | 3.084 (2) | 113 |
Symmetry code: (i) −x+1, −y+1, −z. |