In the title compound, C
31H
35NO
3, the central heterocyclic ring of the octahydroacridinedione system is planar while the outer two rings each adopt an envelope conformation. The buckling angle between the two halves is 8.52 (3)°, which shows the relative planarity of the decahydroacridinedione system. The dihedral angle between the planes of the two aromatic rings is 7.55 (7)°. The crystal structure is stabilized by two intermolecular C—H
O hydrogen bonds that generate
C(10) chains and an
R22(16) ring motif. A weak C—H
π interaction further stabilizes the structure.
Supporting information
CCDC reference: 643106
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.116
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C26 - C30 .. 6.38 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-
p-tolyl-1,2,3,4,5,6,7,8,9,10-
decahydroacridine-1,8-dione
top
Crystal data top
C31H35NO3 | F(000) = 1008 |
Mr = 469.60 | Dx = 1.175 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 33312 reflections |
a = 12.2442 (7) Å | θ = 1.7–28.0° |
b = 11.0188 (5) Å | µ = 0.08 mm−1 |
c = 20.0428 (11) Å | T = 296 K |
β = 100.963 (4)° | Prism, colorless |
V = 2654.8 (2) Å3 | 0.65 × 0.49 × 0.38 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 5228 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3732 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.032 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −15→15 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.963, Tmax = 0.978 | l = −24→24 |
33312 measured reflections | |
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)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1646P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5228 reflections | Δρmax = 0.14 e Å−3 |
317 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0062 (8) |
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 | Occ. (<1) |
C1 | 0.25742 (12) | 0.67107 (12) | 0.33975 (6) | 0.0485 (3) | |
C2 | 0.32975 (13) | 0.76747 (12) | 0.34183 (7) | 0.0557 (3) | |
H2 | 0.4039 | 0.7591 | 0.3628 | 0.067* | |
C3 | 0.29124 (16) | 0.87643 (14) | 0.31252 (8) | 0.0672 (4) | |
H3 | 0.3402 | 0.9414 | 0.3145 | 0.081* | |
C4 | 0.18304 (18) | 0.89147 (16) | 0.28061 (8) | 0.0745 (5) | |
C5 | 0.11176 (15) | 0.79480 (18) | 0.27918 (8) | 0.0768 (5) | |
H5 | 0.0378 | 0.8034 | 0.2577 | 0.092* | |
C6 | 0.14778 (13) | 0.68423 (15) | 0.30913 (8) | 0.0650 (4) | |
H6 | 0.0982 | 0.6201 | 0.3084 | 0.078* | |
C7 | 0.31467 (11) | 0.53451 (12) | 0.43789 (7) | 0.0490 (3) | |
C8 | 0.29355 (14) | 0.63919 (13) | 0.48171 (7) | 0.0577 (4) | |
H8A | 0.2316 | 0.6864 | 0.4575 | 0.069* | |
H8B | 0.3586 | 0.6913 | 0.4897 | 0.069* | |
C9 | 0.26740 (13) | 0.59981 (15) | 0.55037 (7) | 0.0607 (4) | |
C10 | 0.35801 (14) | 0.51158 (15) | 0.58253 (8) | 0.0656 (4) | |
H10A | 0.4265 | 0.5566 | 0.5968 | 0.079* | |
H10B | 0.3374 | 0.4773 | 0.6230 | 0.079* | |
C11 | 0.37985 (12) | 0.40970 (14) | 0.53735 (7) | 0.0579 (4) | |
C12 | 0.35048 (11) | 0.42534 (12) | 0.46384 (7) | 0.0506 (3) | |
C13 | 0.26730 (17) | 0.71117 (18) | 0.59549 (8) | 0.0815 (5) | |
H13A | 0.2099 | 0.7660 | 0.5748 | 0.122* | |
H13B | 0.3382 | 0.7510 | 0.6010 | 0.122* | |
H13C | 0.2538 | 0.6866 | 0.6392 | 0.122* | |
C14 | 0.15318 (15) | 0.53840 (19) | 0.53941 (10) | 0.0817 (5) | |
H14A | 0.0972 | 0.5949 | 0.5188 | 0.122* | |
H14B | 0.1377 | 0.5125 | 0.5824 | 0.122* | |
H14C | 0.1530 | 0.4693 | 0.5102 | 0.122* | |
C15 | 0.36084 (12) | 0.31644 (12) | 0.42008 (7) | 0.0516 (3) | |
H15 | 0.4306 | 0.2749 | 0.4391 | 0.062* | |
C16 | 0.26584 (12) | 0.22749 (12) | 0.42005 (7) | 0.0500 (3) | |
C17 | 0.15641 (12) | 0.26020 (13) | 0.39486 (8) | 0.0596 (4) | |
H17 | 0.1408 | 0.3383 | 0.3782 | 0.072* | |
C18 | 0.07049 (13) | 0.17927 (14) | 0.39398 (8) | 0.0623 (4) | |
H18 | −0.0023 | 0.2030 | 0.3769 | 0.075* | |
C19 | 0.09235 (13) | 0.06274 (13) | 0.41847 (7) | 0.0560 (4) | |
C20 | 0.20011 (13) | 0.02864 (13) | 0.44412 (8) | 0.0596 (4) | |
H20 | 0.2156 | −0.0494 | 0.4610 | 0.072* | |
C21 | 0.28533 (13) | 0.11105 (13) | 0.44461 (7) | 0.0568 (4) | |
H21 | 0.3580 | 0.0873 | 0.4620 | 0.068* | |
C22 | 0.01995 (17) | −0.13011 (15) | 0.44258 (9) | 0.0772 (5) | |
H22A | −0.0495 | −0.1728 | 0.4370 | 0.116* | |
H22B | 0.0522 | −0.1246 | 0.4900 | 0.116* | |
H22C | 0.0698 | −0.1730 | 0.4193 | 0.116* | |
C23 | 0.36728 (11) | 0.35755 (12) | 0.34900 (7) | 0.0497 (3) | |
C24 | 0.41151 (12) | 0.27146 (13) | 0.30554 (8) | 0.0569 (4) | |
C25 | 0.41956 (14) | 0.31092 (14) | 0.23519 (8) | 0.0643 (4) | |
H25A | 0.4158 | 0.2399 | 0.2062 | 0.077* | |
H25B | 0.4912 | 0.3492 | 0.2364 | 0.077* | |
C26 | 0.32797 (14) | 0.39924 (13) | 0.20441 (7) | 0.0588 (4) | |
C27 | 0.33210 (14) | 0.50623 (12) | 0.25305 (7) | 0.0582 (4) | |
H27A | 0.3985 | 0.5535 | 0.2518 | 0.070* | |
H27B | 0.2682 | 0.5580 | 0.2377 | 0.070* | |
C28 | 0.33260 (11) | 0.46831 (12) | 0.32517 (7) | 0.0482 (3) | |
C29 | 0.3469 (2) | 0.44559 (16) | 0.13577 (8) | 0.0874 (6) | |
H29A | 0.4180 | 0.4849 | 0.1415 | 0.131* | |
H29B | 0.2895 | 0.5025 | 0.1177 | 0.131* | |
H29C | 0.3450 | 0.3786 | 0.1050 | 0.131* | |
C30 | 0.21535 (16) | 0.33640 (17) | 0.19540 (10) | 0.0820 (5) | |
H30A | 0.1579 | 0.3924 | 0.1761 | 0.123* | |
H30B | 0.2027 | 0.3092 | 0.2388 | 0.123* | |
H30C | 0.2145 | 0.2680 | 0.1656 | 0.123* | |
C31 | 0.1429 (2) | 1.0110 (2) | 0.24828 (11) | 0.1209 (10) | |
H31A | 0.0653 | 1.0050 | 0.2284 | 0.181* | 0.50 |
H31B | 0.1843 | 1.0306 | 0.2136 | 0.181* | 0.50 |
H31C | 0.1535 | 1.0736 | 0.2822 | 0.181* | 0.50 |
H31D | 0.2034 | 1.0678 | 0.2544 | 0.181* | 0.50 |
H31E | 0.0844 | 1.0422 | 0.2693 | 0.181* | 0.50 |
H31F | 0.1152 | 0.9992 | 0.2006 | 0.181* | 0.50 |
N1 | 0.29742 (10) | 0.55478 (9) | 0.36784 (5) | 0.0502 (3) | |
O1 | 0.42431 (10) | 0.31588 (11) | 0.56186 (6) | 0.0775 (3) | |
O2 | 0.00133 (10) | −0.01126 (10) | 0.41491 (6) | 0.0727 (3) | |
O3 | 0.44344 (11) | 0.17072 (10) | 0.32675 (6) | 0.0806 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0572 (8) | 0.0460 (7) | 0.0430 (7) | 0.0069 (6) | 0.0112 (6) | 0.0024 (5) |
C2 | 0.0625 (9) | 0.0494 (8) | 0.0568 (8) | 0.0030 (7) | 0.0157 (7) | 0.0031 (6) |
C3 | 0.0959 (13) | 0.0471 (8) | 0.0633 (9) | 0.0079 (8) | 0.0268 (9) | 0.0060 (7) |
C4 | 0.1087 (14) | 0.0675 (9) | 0.0505 (8) | 0.0373 (8) | 0.0231 (9) | 0.0073 (7) |
C5 | 0.0694 (11) | 0.0994 (12) | 0.0574 (9) | 0.0341 (8) | 0.0013 (8) | 0.0009 (9) |
C6 | 0.0578 (9) | 0.0730 (10) | 0.0622 (9) | 0.0039 (8) | 0.0063 (7) | −0.0028 (8) |
C7 | 0.0496 (8) | 0.0511 (7) | 0.0461 (7) | −0.0048 (6) | 0.0087 (6) | 0.0031 (6) |
C8 | 0.0665 (9) | 0.0564 (8) | 0.0508 (8) | −0.0015 (7) | 0.0124 (7) | −0.0001 (6) |
C9 | 0.0636 (9) | 0.0717 (9) | 0.0468 (7) | −0.0063 (7) | 0.0108 (7) | −0.0014 (7) |
C10 | 0.0700 (10) | 0.0775 (10) | 0.0468 (8) | −0.0103 (8) | 0.0043 (7) | 0.0049 (7) |
C11 | 0.0546 (8) | 0.0623 (9) | 0.0534 (8) | −0.0096 (7) | 0.0013 (6) | 0.0116 (7) |
C12 | 0.0491 (8) | 0.0518 (7) | 0.0496 (7) | −0.0052 (6) | 0.0063 (6) | 0.0067 (6) |
C13 | 0.0986 (14) | 0.0912 (13) | 0.0557 (9) | −0.0001 (10) | 0.0172 (9) | −0.0113 (9) |
C14 | 0.0654 (11) | 0.1086 (14) | 0.0741 (11) | −0.0123 (10) | 0.0213 (9) | −0.0039 (10) |
C15 | 0.0487 (8) | 0.0490 (7) | 0.0561 (8) | 0.0029 (6) | 0.0072 (6) | 0.0110 (6) |
C16 | 0.0549 (8) | 0.0475 (7) | 0.0478 (7) | 0.0006 (6) | 0.0103 (6) | 0.0052 (6) |
C17 | 0.0585 (9) | 0.0529 (8) | 0.0670 (9) | 0.0032 (7) | 0.0109 (7) | 0.0140 (7) |
C18 | 0.0545 (9) | 0.0666 (9) | 0.0648 (9) | 0.0007 (7) | 0.0088 (7) | 0.0100 (7) |
C19 | 0.0636 (9) | 0.0560 (8) | 0.0493 (7) | −0.0105 (7) | 0.0131 (7) | −0.0009 (6) |
C20 | 0.0722 (10) | 0.0463 (8) | 0.0604 (9) | −0.0021 (7) | 0.0125 (7) | 0.0075 (6) |
C21 | 0.0587 (9) | 0.0518 (8) | 0.0589 (8) | 0.0030 (7) | 0.0081 (7) | 0.0079 (7) |
C22 | 0.0954 (13) | 0.0652 (10) | 0.0722 (10) | −0.0230 (9) | 0.0190 (9) | 0.0045 (8) |
C23 | 0.0478 (7) | 0.0469 (7) | 0.0550 (8) | 0.0004 (6) | 0.0111 (6) | 0.0051 (6) |
C24 | 0.0519 (8) | 0.0514 (8) | 0.0681 (9) | 0.0051 (6) | 0.0134 (7) | 0.0027 (7) |
C25 | 0.0736 (10) | 0.0584 (9) | 0.0647 (9) | 0.0075 (7) | 0.0228 (8) | −0.0031 (7) |
C26 | 0.0777 (10) | 0.0468 (7) | 0.0522 (8) | 0.0011 (7) | 0.0127 (7) | −0.0011 (6) |
C27 | 0.0822 (11) | 0.0440 (7) | 0.0515 (8) | 0.0005 (7) | 0.0207 (7) | 0.0035 (6) |
C28 | 0.0504 (8) | 0.0442 (7) | 0.0511 (7) | −0.0018 (6) | 0.0124 (6) | 0.0021 (6) |
C29 | 0.1512 (19) | 0.0616 (10) | 0.0541 (9) | 0.0077 (11) | 0.0310 (10) | −0.0017 (8) |
C30 | 0.0847 (13) | 0.0704 (11) | 0.0814 (12) | −0.0026 (9) | −0.0082 (10) | 0.0006 (9) |
C31 | 0.195 (3) | 0.0917 (15) | 0.0796 (13) | 0.0788 (17) | 0.0364 (15) | 0.0269 (11) |
N1 | 0.0634 (7) | 0.0425 (6) | 0.0457 (6) | 0.0040 (5) | 0.0127 (5) | 0.0048 (5) |
O1 | 0.0901 (8) | 0.0722 (7) | 0.0631 (7) | 0.0030 (6) | −0.0034 (6) | 0.0208 (6) |
O2 | 0.0725 (7) | 0.0671 (7) | 0.0766 (7) | −0.0189 (6) | 0.0092 (6) | 0.0052 (6) |
O3 | 0.0959 (9) | 0.0595 (7) | 0.0911 (8) | 0.0287 (6) | 0.0299 (7) | 0.0137 (6) |
Geometric parameters (Å, º) top
C1—C6 | 1.374 (2) | C17—H17 | 0.9300 |
C1—C2 | 1.379 (2) | C18—C19 | 1.383 (2) |
C1—N1 | 1.4470 (16) | C18—H18 | 0.9300 |
C2—C3 | 1.380 (2) | C19—O2 | 1.3717 (18) |
C2—H2 | 0.9300 | C19—C20 | 1.374 (2) |
C3—C4 | 1.367 (3) | C20—C21 | 1.382 (2) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.374 (3) | C21—H21 | 0.9300 |
C4—C31 | 1.508 (2) | C22—O2 | 1.424 (2) |
C5—C6 | 1.392 (2) | C22—H22A | 0.9600 |
C5—H5 | 0.9300 | C22—H22B | 0.9600 |
C6—H6 | 0.9300 | C22—H22C | 0.9600 |
C7—C12 | 1.3502 (19) | C23—C28 | 1.3493 (18) |
C7—N1 | 1.3974 (17) | C23—C24 | 1.460 (2) |
C7—C8 | 1.502 (2) | C24—O3 | 1.2258 (17) |
C8—C9 | 1.534 (2) | C24—C25 | 1.497 (2) |
C8—H8A | 0.9700 | C25—C26 | 1.524 (2) |
C8—H8B | 0.9700 | C25—H25A | 0.9700 |
C9—C10 | 1.523 (2) | C25—H25B | 0.9700 |
C9—C13 | 1.524 (2) | C26—C30 | 1.523 (2) |
C9—C14 | 1.531 (2) | C26—C27 | 1.5244 (19) |
C10—C11 | 1.498 (2) | C26—C29 | 1.526 (2) |
C10—H10A | 0.9700 | C27—C28 | 1.5035 (19) |
C10—H10B | 0.9700 | C27—H27A | 0.9700 |
C11—O1 | 1.2266 (18) | C27—H27B | 0.9700 |
C11—C12 | 1.4588 (19) | C28—N1 | 1.4017 (17) |
C12—C15 | 1.506 (2) | C29—H29A | 0.9600 |
C13—H13A | 0.9600 | C29—H29B | 0.9600 |
C13—H13B | 0.9600 | C29—H29C | 0.9600 |
C13—H13C | 0.9600 | C30—H30A | 0.9600 |
C14—H14A | 0.9600 | C30—H30B | 0.9600 |
C14—H14B | 0.9600 | C30—H30C | 0.9600 |
C14—H14C | 0.9600 | C31—H31A | 0.9600 |
C15—C23 | 1.5113 (19) | C31—H31B | 0.9600 |
C15—C16 | 1.5210 (19) | C31—H31C | 0.9600 |
C15—H15 | 0.9800 | C31—H31D | 0.9600 |
C16—C21 | 1.3786 (19) | C31—H31E | 0.9600 |
C16—C17 | 1.387 (2) | C31—H31F | 0.9600 |
C17—C18 | 1.377 (2) | | |
| | | |
C6—C1—C2 | 119.98 (13) | C19—C20—H20 | 120.2 |
C6—C1—N1 | 119.81 (13) | C21—C20—H20 | 120.2 |
C2—C1—N1 | 120.18 (13) | C16—C21—C20 | 122.00 (14) |
C1—C2—C3 | 119.48 (15) | C16—C21—H21 | 119.0 |
C1—C2—H2 | 120.3 | C20—C21—H21 | 119.0 |
C3—C2—H2 | 120.3 | O2—C22—H22A | 109.5 |
C4—C3—C2 | 121.80 (17) | O2—C22—H22B | 109.5 |
C4—C3—H3 | 119.1 | H22A—C22—H22B | 109.5 |
C2—C3—H3 | 119.1 | O2—C22—H22C | 109.5 |
C3—C4—C5 | 118.09 (15) | H22A—C22—H22C | 109.5 |
C3—C4—C31 | 121.0 (2) | H22B—C22—H22C | 109.5 |
C5—C4—C31 | 120.9 (2) | C28—C23—C24 | 120.27 (13) |
C4—C5—C6 | 121.44 (16) | C28—C23—C15 | 122.38 (12) |
C4—C5—H5 | 119.3 | C24—C23—C15 | 117.35 (12) |
C6—C5—H5 | 119.3 | O3—C24—C23 | 120.76 (14) |
C1—C6—C5 | 119.19 (16) | O3—C24—C25 | 121.07 (14) |
C1—C6—H6 | 120.4 | C23—C24—C25 | 118.15 (12) |
C5—C6—H6 | 120.4 | C24—C25—C26 | 113.05 (13) |
C12—C7—N1 | 120.36 (12) | C24—C25—H25A | 109.0 |
C12—C7—C8 | 122.57 (12) | C26—C25—H25A | 109.0 |
N1—C7—C8 | 117.06 (11) | C24—C25—H25B | 109.0 |
C7—C8—C9 | 113.33 (12) | C26—C25—H25B | 109.0 |
C7—C8—H8A | 108.9 | H25A—C25—H25B | 107.8 |
C9—C8—H8A | 108.9 | C30—C26—C25 | 109.74 (13) |
C7—C8—H8B | 108.9 | C30—C26—C27 | 110.29 (14) |
C9—C8—H8B | 108.9 | C25—C26—C27 | 107.62 (12) |
H8A—C8—H8B | 107.7 | C30—C26—C29 | 109.54 (15) |
C10—C9—C13 | 110.21 (13) | C25—C26—C29 | 110.64 (14) |
C10—C9—C14 | 110.52 (14) | C27—C26—C29 | 109.00 (12) |
C13—C9—C14 | 109.69 (15) | C28—C27—C26 | 113.17 (11) |
C10—C9—C8 | 107.51 (13) | C28—C27—H27A | 108.9 |
C13—C9—C8 | 109.17 (13) | C26—C27—H27A | 108.9 |
C14—C9—C8 | 109.70 (13) | C28—C27—H27B | 108.9 |
C11—C10—C9 | 114.96 (12) | C26—C27—H27B | 108.9 |
C11—C10—H10A | 108.5 | H27A—C27—H27B | 107.8 |
C9—C10—H10A | 108.5 | C23—C28—N1 | 120.75 (12) |
C11—C10—H10B | 108.5 | C23—C28—C27 | 122.35 (12) |
C9—C10—H10B | 108.5 | N1—C28—C27 | 116.88 (11) |
H10A—C10—H10B | 107.5 | C26—C29—H29A | 109.5 |
O1—C11—C12 | 120.63 (14) | C26—C29—H29B | 109.5 |
O1—C11—C10 | 120.40 (13) | H29A—C29—H29B | 109.5 |
C12—C11—C10 | 118.94 (13) | C26—C29—H29C | 109.5 |
C7—C12—C11 | 119.60 (13) | H29A—C29—H29C | 109.5 |
C7—C12—C15 | 122.87 (12) | H29B—C29—H29C | 109.5 |
C11—C12—C15 | 117.53 (12) | C26—C30—H30A | 109.5 |
C9—C13—H13A | 109.5 | C26—C30—H30B | 109.5 |
C9—C13—H13B | 109.5 | H30A—C30—H30B | 109.5 |
H13A—C13—H13B | 109.5 | C26—C30—H30C | 109.5 |
C9—C13—H13C | 109.5 | H30A—C30—H30C | 109.5 |
H13A—C13—H13C | 109.5 | H30B—C30—H30C | 109.5 |
H13B—C13—H13C | 109.5 | C4—C31—H31A | 109.5 |
C9—C14—H14A | 109.5 | C4—C31—H31B | 109.5 |
C9—C14—H14B | 109.5 | H31A—C31—H31B | 109.5 |
H14A—C14—H14B | 109.5 | C4—C31—H31C | 109.5 |
C9—C14—H14C | 109.5 | H31A—C31—H31C | 109.5 |
H14A—C14—H14C | 109.5 | H31B—C31—H31C | 109.5 |
H14B—C14—H14C | 109.5 | C4—C31—H31D | 109.5 |
C12—C15—C23 | 109.60 (11) | H31A—C31—H31D | 141.1 |
C12—C15—C16 | 111.38 (12) | H31B—C31—H31D | 56.3 |
C23—C15—C16 | 111.70 (11) | H31C—C31—H31D | 56.3 |
C12—C15—H15 | 108.0 | C4—C31—H31E | 109.5 |
C23—C15—H15 | 108.0 | H31A—C31—H31E | 56.3 |
C16—C15—H15 | 108.0 | H31B—C31—H31E | 141.1 |
C21—C16—C17 | 117.49 (13) | H31C—C31—H31E | 56.3 |
C21—C16—C15 | 121.27 (13) | H31D—C31—H31E | 109.5 |
C17—C16—C15 | 121.24 (12) | C4—C31—H31F | 109.5 |
C18—C17—C16 | 121.29 (13) | H31A—C31—H31F | 56.3 |
C18—C17—H17 | 119.4 | H31B—C31—H31F | 56.3 |
C16—C17—H17 | 119.4 | H31C—C31—H31F | 141.1 |
C17—C18—C19 | 120.08 (14) | H31D—C31—H31F | 109.5 |
C17—C18—H18 | 120.0 | H31E—C31—H31F | 109.5 |
C19—C18—H18 | 120.0 | C7—N1—C28 | 119.94 (11) |
O2—C19—C20 | 124.72 (13) | C7—N1—C1 | 120.51 (11) |
O2—C19—C18 | 115.67 (14) | C28—N1—C1 | 119.02 (10) |
C20—C19—C18 | 119.61 (14) | C19—O2—C22 | 117.28 (13) |
C19—C20—C21 | 119.53 (13) | | |
| | | |
C6—C1—C2—C3 | −0.5 (2) | O2—C19—C20—C21 | 179.52 (14) |
N1—C1—C2—C3 | 177.52 (12) | C18—C19—C20—C21 | −0.5 (2) |
C1—C2—C3—C4 | −0.7 (2) | C17—C16—C21—C20 | 0.4 (2) |
C2—C3—C4—C5 | 1.0 (2) | C15—C16—C21—C20 | −179.12 (13) |
C2—C3—C4—C31 | −179.39 (16) | C19—C20—C21—C16 | 0.0 (2) |
C3—C4—C5—C6 | −0.1 (3) | C12—C15—C23—C28 | −19.50 (18) |
C31—C4—C5—C6 | −179.69 (15) | C16—C15—C23—C28 | 104.43 (15) |
C2—C1—C6—C5 | 1.4 (2) | C12—C15—C23—C24 | 161.41 (12) |
N1—C1—C6—C5 | −176.66 (13) | C16—C15—C23—C24 | −74.66 (16) |
C4—C5—C6—C1 | −1.1 (2) | C28—C23—C24—O3 | 179.84 (14) |
C12—C7—C8—C9 | −24.7 (2) | C15—C23—C24—O3 | −1.1 (2) |
N1—C7—C8—C9 | 156.36 (12) | C28—C23—C24—C25 | 1.5 (2) |
C7—C8—C9—C10 | 50.72 (17) | C15—C23—C24—C25 | −179.42 (13) |
C7—C8—C9—C13 | 170.27 (14) | O3—C24—C25—C26 | 149.38 (15) |
C7—C8—C9—C14 | −69.50 (18) | C23—C24—C25—C26 | −32.3 (2) |
C13—C9—C10—C11 | −169.46 (14) | C24—C25—C26—C30 | −64.49 (18) |
C14—C9—C10—C11 | 69.13 (18) | C24—C25—C26—C27 | 55.54 (17) |
C8—C9—C10—C11 | −50.57 (17) | C24—C25—C26—C29 | 174.53 (14) |
C9—C10—C11—O1 | −158.20 (14) | C30—C26—C27—C28 | 68.88 (17) |
C9—C10—C11—C12 | 23.6 (2) | C25—C26—C27—C28 | −50.80 (18) |
N1—C7—C12—C11 | 173.21 (12) | C29—C26—C27—C28 | −170.83 (14) |
C8—C7—C12—C11 | −5.7 (2) | C24—C23—C28—N1 | −175.42 (12) |
N1—C7—C12—C15 | −7.4 (2) | C15—C23—C28—N1 | 5.5 (2) |
C8—C7—C12—C15 | 173.68 (13) | C24—C23—C28—C27 | 3.1 (2) |
O1—C11—C12—C7 | −171.69 (14) | C15—C23—C28—C27 | −175.94 (13) |
C10—C11—C12—C7 | 6.5 (2) | C26—C27—C28—C23 | 23.2 (2) |
O1—C11—C12—C15 | 8.9 (2) | C26—C27—C28—N1 | −158.17 (13) |
C10—C11—C12—C15 | −172.93 (13) | C12—C7—N1—C28 | −9.40 (19) |
C7—C12—C15—C23 | 20.53 (19) | C8—C7—N1—C28 | 169.57 (12) |
C11—C12—C15—C23 | −160.08 (12) | C12—C7—N1—C1 | 179.05 (13) |
C7—C12—C15—C16 | −103.59 (15) | C8—C7—N1—C1 | −1.97 (19) |
C11—C12—C15—C16 | 75.80 (15) | C23—C28—N1—C7 | 10.33 (19) |
C12—C15—C16—C21 | −117.90 (14) | C27—C28—N1—C7 | −168.29 (12) |
C23—C15—C16—C21 | 119.18 (14) | C23—C28—N1—C1 | −177.99 (12) |
C12—C15—C16—C17 | 62.57 (17) | C27—C28—N1—C1 | 3.38 (18) |
C23—C15—C16—C17 | −60.35 (17) | C6—C1—N1—C7 | −102.49 (16) |
C21—C16—C17—C18 | −0.4 (2) | C2—C1—N1—C7 | 79.49 (17) |
C15—C16—C17—C18 | 179.13 (14) | C6—C1—N1—C28 | 85.89 (17) |
C16—C17—C18—C19 | 0.0 (2) | C2—C1—N1—C28 | −92.13 (16) |
C17—C18—C19—O2 | −179.52 (14) | C20—C19—O2—C22 | 2.9 (2) |
C17—C18—C19—C20 | 0.5 (2) | C18—C19—O2—C22 | −177.11 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.49 | 3.3804 (19) | 162 |
C29—H29C···O1ii | 0.96 | 2.57 | 3.454 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2. |