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The title compound, C17H17NO, is one of the diastereoisomers formed as result of a Diels-Alder reaction catalysed by zirconium tetrachloride. The compound crystallizes with two crystallographically independent molecules in the asymmetric unit. The N-heterocyclic ring adopts a half-chair conformation for both molecules. Only one molecule forms a hydrogen bond; for the other, no acceptor for the NH group is found.
Supporting information
CCDC reference: 298371
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.117
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5A
PLAT420_ALERT_2_C D-H Without Acceptor N1A - H1AN ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
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
0 ALERT type 3 Indicator that the structure quality may be low
1 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: SHELXTL/PC (Sheldrick, 1990) and QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97.
2,3,3a,4,5,9 b-hexahydro-4-phenylfuro[3,2-
c]quinoline
top
Crystal data top
C17H17NO | Z = 4 |
Mr = 251.32 | F(000) = 536 |
Triclinic, P1 | Dx = 1.255 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3760 (6) Å | Cell parameters from 6873 reflections |
b = 9.9065 (6) Å | θ = 2.3–28.0° |
c = 16.014 (1) Å | µ = 0.08 mm−1 |
α = 96.954 (1)° | T = 273 K |
β = 102.005 (1)° | Block, yellow |
γ = 110.693 (1)° | 0.20 × 0.15 × 0.10 mm |
V = 1329.92 (14) Å3 | |
Data collection top
CCD area detector diffractometer | 4015 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 1.3° |
ω scans | h = −11→11 |
12802 measured reflections | k = −11→11 |
4659 independent reflections | l = −19→19 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2842P] where P = (Fo2 + 2Fc2)/3 |
4659 reflections | (Δ/σ)max = 0.001 |
351 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.30 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.77910 (16) | 0.08159 (15) | 0.78817 (7) | 0.0743 (4) | |
N1A | 1.01774 (16) | 0.27278 (17) | 1.03847 (9) | 0.0597 (4) | |
H1AN | 1.070 (2) | 0.306 (2) | 1.0909 (14) | 0.071 (6)* | |
C1A | 1.2738 (2) | 0.1788 (2) | 0.87210 (12) | 0.0635 (5) | |
H1A | 1.3311 | 0.1621 | 0.8339 | 0.076* | |
C2A | 1.1111 (2) | 0.11518 (18) | 0.84756 (10) | 0.0572 (4) | |
H2A | 1.0593 | 0.0540 | 0.7925 | 0.069* | |
C3A | 1.02159 (18) | 0.13949 (16) | 0.90240 (9) | 0.0479 (3) | |
C4A | 0.84285 (19) | 0.06555 (17) | 0.87404 (9) | 0.0537 (4) | |
H4A | 0.8108 | −0.0398 | 0.8746 | 0.064* | |
C5A | 0.7180 (3) | 0.1903 (3) | 0.79355 (12) | 0.0919 (7) | |
H5A1 | 0.6054 | 0.1479 | 0.7647 | 0.110* | |
H5A2 | 0.7693 | 0.2667 | 0.7646 | 0.110* | |
C6A | 0.7458 (2) | 0.25531 (19) | 0.88777 (10) | 0.0556 (4) | |
H6A1 | 0.6565 | 0.2764 | 0.8976 | 0.067* | |
H6A2 | 0.8409 | 0.3451 | 0.9082 | 0.067* | |
C7A | 0.76430 (17) | 0.13258 (16) | 0.93181 (9) | 0.0470 (3) | |
H7A | 0.6582 | 0.0587 | 0.9254 | 0.056* | |
C8A | 0.85396 (17) | 0.17638 (16) | 1.02846 (9) | 0.0479 (3) | |
H8A | 0.8531 | 0.0867 | 1.0487 | 0.057* | |
C9A | 1.10078 (18) | 0.23379 (18) | 0.98428 (9) | 0.0503 (4) | |
C10A | 1.2660 (2) | 0.2950 (2) | 1.00959 (11) | 0.0634 (4) | |
H10A | 1.3192 | 0.3552 | 1.0648 | 0.076* | |
C11A | 1.3509 (2) | 0.2676 (2) | 0.95432 (12) | 0.0669 (5) | |
H11A | 1.4610 | 0.3091 | 0.9723 | 0.080* | |
C12A | 0.77944 (16) | 0.25081 (16) | 1.08392 (9) | 0.0435 (3) | |
C13A | 0.82279 (18) | 0.40242 (17) | 1.10068 (10) | 0.0519 (4) | |
H13A | 0.8980 | 0.4605 | 1.0762 | 0.062* | |
C14A | 0.7561 (2) | 0.46834 (19) | 1.15309 (11) | 0.0616 (4) | |
H14A | 0.7872 | 0.5704 | 1.1643 | 0.074* | |
C15A | 0.6434 (2) | 0.3834 (2) | 1.18886 (11) | 0.0631 (4) | |
H15A | 0.5989 | 0.4279 | 1.2246 | 0.076* | |
C16A | 0.59681 (19) | 0.2326 (2) | 1.17163 (11) | 0.0597 (4) | |
H16 | 0.5194 | 0.1747 | 1.1949 | 0.072* | |
C17A | 0.66497 (18) | 0.16713 (17) | 1.11982 (10) | 0.0516 (4) | |
H17A | 0.6335 | 0.0651 | 1.1088 | 0.062* | |
O1B | 0.65030 (16) | 0.82618 (15) | 0.33740 (7) | 0.0709 (3) | |
N1B | 0.77909 (17) | 0.99048 (15) | 0.59852 (9) | 0.0563 (3) | |
H1BN | 0.793 (2) | 1.0273 (19) | 0.6513 (13) | 0.061 (5)* | |
C1B | 0.7737 (2) | 1.2841 (2) | 0.43316 (14) | 0.0729 (5) | |
H1B | 0.7779 | 1.3496 | 0.3959 | 0.087* | |
C2B | 0.7039 (2) | 1.1344 (2) | 0.40015 (12) | 0.0663 (5) | |
H2B | 0.6600 | 1.0998 | 0.3402 | 0.080* | |
C3B | 0.69682 (17) | 1.03292 (18) | 0.45371 (10) | 0.0522 (4) | |
C4B | 0.61237 (19) | 0.86900 (19) | 0.41573 (10) | 0.0563 (4) | |
H4B | 0.4978 | 0.8421 | 0.4031 | 0.068* | |
C5B | 0.7851 (2) | 0.7896 (2) | 0.36130 (11) | 0.0693 (5) | |
H5B1 | 0.8777 | 0.8659 | 0.3539 | 0.083* | |
H5B2 | 0.7676 | 0.6970 | 0.3244 | 0.083* | |
C6B | 0.8106 (2) | 0.7762 (2) | 0.45578 (10) | 0.0579 (4) | |
H6B1 | 0.9031 | 0.8588 | 0.4929 | 0.070* | |
H6B2 | 0.8235 | 0.6850 | 0.4629 | 0.070* | |
C7B | 0.65973 (17) | 0.77712 (17) | 0.47689 (9) | 0.0502 (4) | |
H7B | 0.5792 | 0.6761 | 0.4584 | 0.060* | |
C8B | 0.67282 (17) | 0.83520 (17) | 0.57204 (9) | 0.0494 (4) | |
H8B | 0.5676 | 0.8271 | 0.5767 | 0.059* | |
C9B | 0.76801 (17) | 1.08609 (17) | 0.54340 (10) | 0.0504 (4) | |
C10B | 0.8357 (2) | 1.23865 (19) | 0.57643 (12) | 0.0619 (4) | |
H10B | 0.8803 | 1.2748 | 0.6362 | 0.074* | |
C11B | 0.8374 (2) | 1.3362 (2) | 0.52200 (14) | 0.0692 (5) | |
H11B | 0.8816 | 1.4373 | 0.5452 | 0.083* | |
C12B | 0.72866 (17) | 0.74569 (16) | 0.63121 (9) | 0.0482 (3) | |
C13B | 0.88806 (19) | 0.77285 (18) | 0.66251 (10) | 0.0569 (4) | |
H13B | 0.9638 | 0.8515 | 0.6495 | 0.068* | |
C14B | 0.9357 (2) | 0.6847 (2) | 0.71270 (11) | 0.0647 (4) | |
H14B | 1.0428 | 0.7039 | 0.7330 | 0.078* | |
C15B | 0.8252 (2) | 0.56858 (19) | 0.73280 (11) | 0.0640 (4) | |
H15B | 0.8575 | 0.5097 | 0.7670 | 0.077* | |
C16B | 0.6670 (2) | 0.5396 (2) | 0.70227 (12) | 0.0677 (5) | |
H16B | 0.5920 | 0.4604 | 0.7153 | 0.081* | |
C17B | 0.6195 (2) | 0.62800 (19) | 0.65227 (11) | 0.0595 (4) | |
H17B | 0.5121 | 0.6082 | 0.6324 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0886 (9) | 0.1004 (10) | 0.0384 (6) | 0.0548 (8) | 0.0031 (6) | −0.0003 (6) |
N1A | 0.0448 (7) | 0.0852 (10) | 0.0410 (7) | 0.0267 (7) | 0.0047 (6) | −0.0077 (7) |
C1A | 0.0794 (12) | 0.0752 (11) | 0.0652 (11) | 0.0495 (10) | 0.0383 (9) | 0.0278 (9) |
C2A | 0.0823 (12) | 0.0569 (9) | 0.0462 (8) | 0.0391 (9) | 0.0231 (8) | 0.0141 (7) |
C3A | 0.0624 (9) | 0.0485 (8) | 0.0416 (8) | 0.0305 (7) | 0.0140 (7) | 0.0134 (6) |
C4A | 0.0645 (10) | 0.0494 (8) | 0.0432 (8) | 0.0236 (7) | 0.0072 (7) | 0.0039 (6) |
C5A | 0.150 (2) | 0.1014 (16) | 0.0499 (11) | 0.0797 (16) | 0.0223 (12) | 0.0208 (10) |
C6A | 0.0590 (9) | 0.0649 (10) | 0.0490 (9) | 0.0316 (8) | 0.0128 (7) | 0.0142 (7) |
C7A | 0.0427 (8) | 0.0446 (8) | 0.0446 (8) | 0.0099 (6) | 0.0080 (6) | 0.0057 (6) |
C8A | 0.0546 (8) | 0.0512 (8) | 0.0422 (8) | 0.0255 (7) | 0.0127 (6) | 0.0115 (6) |
C9A | 0.0539 (9) | 0.0627 (9) | 0.0422 (8) | 0.0325 (7) | 0.0116 (6) | 0.0111 (7) |
C10A | 0.0528 (9) | 0.0878 (12) | 0.0515 (9) | 0.0348 (9) | 0.0089 (7) | 0.0072 (8) |
C11A | 0.0581 (10) | 0.0895 (13) | 0.0691 (11) | 0.0413 (9) | 0.0240 (9) | 0.0237 (10) |
C12A | 0.0434 (7) | 0.0496 (8) | 0.0377 (7) | 0.0198 (6) | 0.0077 (6) | 0.0108 (6) |
C13A | 0.0551 (9) | 0.0505 (8) | 0.0524 (9) | 0.0195 (7) | 0.0191 (7) | 0.0152 (7) |
C14A | 0.0730 (11) | 0.0520 (9) | 0.0654 (10) | 0.0300 (8) | 0.0221 (9) | 0.0096 (8) |
C15A | 0.0653 (10) | 0.0766 (12) | 0.0557 (10) | 0.0359 (9) | 0.0227 (8) | 0.0071 (8) |
C16A | 0.0520 (9) | 0.0734 (11) | 0.0547 (9) | 0.0205 (8) | 0.0215 (7) | 0.0177 (8) |
C17A | 0.0506 (8) | 0.0499 (8) | 0.0515 (8) | 0.0164 (7) | 0.0124 (7) | 0.0128 (7) |
O1B | 0.0824 (8) | 0.0910 (9) | 0.0391 (6) | 0.0381 (7) | 0.0115 (5) | 0.0088 (6) |
N1B | 0.0727 (9) | 0.0557 (8) | 0.0390 (7) | 0.0256 (7) | 0.0145 (6) | 0.0040 (6) |
C1B | 0.0716 (12) | 0.0803 (13) | 0.0866 (14) | 0.0387 (10) | 0.0335 (10) | 0.0406 (11) |
C2B | 0.0612 (10) | 0.0874 (13) | 0.0609 (10) | 0.0364 (10) | 0.0184 (8) | 0.0286 (9) |
C3B | 0.0448 (8) | 0.0677 (10) | 0.0520 (9) | 0.0279 (7) | 0.0168 (7) | 0.0161 (7) |
C4B | 0.0479 (8) | 0.0758 (11) | 0.0431 (8) | 0.0244 (8) | 0.0085 (6) | 0.0103 (7) |
C5B | 0.0720 (11) | 0.0861 (13) | 0.0510 (10) | 0.0305 (10) | 0.0229 (8) | 0.0085 (9) |
C6B | 0.0635 (10) | 0.0671 (10) | 0.0485 (9) | 0.0316 (8) | 0.0184 (7) | 0.0070 (7) |
C7B | 0.0466 (8) | 0.0532 (8) | 0.0419 (8) | 0.0134 (7) | 0.0079 (6) | 0.0039 (6) |
C8B | 0.0461 (8) | 0.0594 (9) | 0.0449 (8) | 0.0212 (7) | 0.0164 (6) | 0.0100 (7) |
C9B | 0.0493 (8) | 0.0607 (9) | 0.0501 (8) | 0.0269 (7) | 0.0212 (7) | 0.0132 (7) |
C10B | 0.0667 (10) | 0.0620 (10) | 0.0617 (10) | 0.0272 (8) | 0.0259 (8) | 0.0091 (8) |
C11B | 0.0679 (11) | 0.0619 (10) | 0.0894 (14) | 0.0288 (9) | 0.0352 (10) | 0.0227 (10) |
C12B | 0.0522 (8) | 0.0527 (8) | 0.0376 (7) | 0.0189 (7) | 0.0140 (6) | 0.0037 (6) |
C13B | 0.0515 (9) | 0.0606 (10) | 0.0473 (9) | 0.0127 (7) | 0.0073 (7) | 0.0099 (7) |
C14B | 0.0598 (10) | 0.0720 (11) | 0.0516 (9) | 0.0237 (9) | 0.0002 (8) | 0.0069 (8) |
C15B | 0.0802 (12) | 0.0585 (10) | 0.0483 (9) | 0.0277 (9) | 0.0069 (8) | 0.0091 (7) |
C16B | 0.0763 (12) | 0.0591 (10) | 0.0632 (11) | 0.0175 (9) | 0.0228 (9) | 0.0173 (8) |
C17B | 0.0538 (9) | 0.0657 (10) | 0.0586 (10) | 0.0198 (8) | 0.0195 (7) | 0.0148 (8) |
Geometric parameters (Å, º) top
O1A—C5A | 1.389 (2) | O1B—C5B | 1.425 (2) |
O1A—C4A | 1.4324 (19) | O1B—C4B | 1.4294 (19) |
N1A—C9A | 1.3860 (19) | N1B—C9B | 1.386 (2) |
N1A—C8A | 1.456 (2) | N1B—C8B | 1.457 (2) |
N1A—H1AN | 0.84 (2) | N1B—H1BN | 0.844 (19) |
C1A—C2A | 1.375 (3) | C1B—C2B | 1.374 (3) |
C1A—C11A | 1.380 (3) | C1B—C11B | 1.378 (3) |
C1A—H1A | 0.9300 | C1B—H1B | 0.9300 |
C2A—C3A | 1.390 (2) | C2B—C3B | 1.391 (2) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C9A | 1.397 (2) | C3B—C9B | 1.398 (2) |
C3A—C4A | 1.512 (2) | C3B—C4B | 1.512 (2) |
C4A—C7A | 1.523 (2) | C4B—C7B | 1.518 (2) |
C4A—H4A | 0.9800 | C4B—H4B | 0.9800 |
C5A—C6A | 1.497 (2) | C5B—C6B | 1.511 (2) |
C5A—H5A1 | 0.9700 | C5B—H5B1 | 0.9700 |
C5A—H5A2 | 0.9700 | C5B—H5B2 | 0.9700 |
C6A—C7A | 1.520 (2) | C6B—C7B | 1.524 (2) |
C6A—H6A1 | 0.9700 | C6B—H6B1 | 0.9700 |
C6A—H6A2 | 0.9700 | C6B—H6B2 | 0.9700 |
C7A—C8A | 1.526 (2) | C7B—C8B | 1.526 (2) |
C7A—H7A | 0.9800 | C7B—H7B | 0.9800 |
C8A—C12A | 1.511 (2) | C8B—C12B | 1.511 (2) |
C8A—H8A | 0.9800 | C8B—H8B | 0.9800 |
C9A—C10A | 1.395 (2) | C9B—C10B | 1.398 (2) |
C10A—C11A | 1.371 (2) | C10B—C11B | 1.376 (3) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C17A | 1.383 (2) | C12B—C17B | 1.384 (2) |
C12A—C13A | 1.385 (2) | C12B—C13B | 1.389 (2) |
C13A—C14A | 1.377 (2) | C13B—C14B | 1.380 (2) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.376 (3) | C14B—C15B | 1.373 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.374 (3) | C15B—C16B | 1.372 (3) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.378 (2) | C16B—C17B | 1.380 (2) |
C16A—H16 | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
| | | |
C5A—O1A—C4A | 109.95 (13) | C5B—O1B—C4B | 107.84 (12) |
C9A—N1A—C8A | 119.50 (13) | C9B—N1B—C8B | 120.02 (13) |
C9A—N1A—H1AN | 114.1 (13) | C9B—N1B—H1BN | 113.1 (12) |
C8A—N1A—H1AN | 112.5 (13) | C8B—N1B—H1BN | 113.3 (12) |
C2A—C1A—C11A | 118.98 (15) | C2B—C1B—C11B | 119.37 (17) |
C2A—C1A—H1A | 120.5 | C2B—C1B—H1B | 120.3 |
C11A—C1A—H1A | 120.5 | C11B—C1B—H1B | 120.3 |
C1A—C2A—C3A | 122.09 (16) | C1B—C2B—C3B | 121.99 (18) |
C1A—C2A—H2A | 119.0 | C1B—C2B—H2B | 119.0 |
C3A—C2A—H2A | 119.0 | C3B—C2B—H2B | 119.0 |
C2A—C3A—C9A | 118.38 (15) | C2B—C3B—C9B | 118.50 (16) |
C2A—C3A—C4A | 120.75 (14) | C2B—C3B—C4B | 120.62 (15) |
C9A—C3A—C4A | 120.87 (13) | C9B—C3B—C4B | 120.88 (14) |
O1A—C4A—C3A | 111.68 (13) | O1B—C4B—C3B | 112.19 (13) |
O1A—C4A—C7A | 104.54 (12) | O1B—C4B—C7B | 104.62 (13) |
C3A—C4A—C7A | 113.05 (12) | C3B—C4B—C7B | 112.38 (12) |
O1A—C4A—H4A | 109.1 | O1B—C4B—H4B | 109.2 |
C3A—C4A—H4A | 109.1 | C3B—C4B—H4B | 109.2 |
C7A—C4A—H4A | 109.1 | C7B—C4B—H4B | 109.2 |
O1A—C5A—C6A | 109.00 (15) | O1B—C5B—C6B | 108.28 (13) |
O1A—C5A—H5A1 | 109.9 | O1B—C5B—H5B1 | 110.0 |
C6A—C5A—H5A1 | 109.9 | C6B—C5B—H5B1 | 110.0 |
O1A—C5A—H5A2 | 109.9 | O1B—C5B—H5B2 | 110.0 |
C6A—C5A—H5A2 | 109.9 | C6B—C5B—H5B2 | 110.0 |
H5A1—C5A—H5A2 | 108.3 | H5B1—C5B—H5B2 | 108.4 |
C5A—C6A—C7A | 102.00 (14) | C5B—C6B—C7B | 103.47 (13) |
C5A—C6A—H6A1 | 111.4 | C5B—C6B—H6B1 | 111.1 |
C7A—C6A—H6A1 | 111.4 | C7B—C6B—H6B1 | 111.1 |
C5A—C6A—H6A2 | 111.4 | C5B—C6B—H6B2 | 111.1 |
C7A—C6A—H6A2 | 111.4 | C7B—C6B—H6B2 | 111.1 |
H6A1—C6A—H6A2 | 109.2 | H6B1—C6B—H6B2 | 109.0 |
C6A—C7A—C4A | 102.10 (12) | C4B—C7B—C6B | 101.68 (12) |
C6A—C7A—C8A | 117.08 (12) | C4B—C7B—C8B | 113.03 (13) |
C4A—C7A—C8A | 113.29 (12) | C6B—C7B—C8B | 116.80 (13) |
C6A—C7A—H7A | 108.0 | C4B—C7B—H7B | 108.3 |
C4A—C7A—H7A | 108.0 | C6B—C7B—H7B | 108.3 |
C8A—C7A—H7A | 108.0 | C8B—C7B—H7B | 108.3 |
N1A—C8A—C12A | 110.43 (12) | N1B—C8B—C12B | 110.93 (12) |
N1A—C8A—C7A | 109.03 (12) | N1B—C8B—C7B | 109.57 (12) |
C12A—C8A—C7A | 112.43 (12) | C12B—C8B—C7B | 111.29 (12) |
N1A—C8A—H8A | 108.3 | N1B—C8B—H8B | 108.3 |
C12A—C8A—H8A | 108.3 | C12B—C8B—H8B | 108.3 |
C7A—C8A—H8A | 108.3 | C7B—C8B—H8B | 108.3 |
N1A—C9A—C10A | 119.80 (14) | N1B—C9B—C10B | 120.06 (14) |
N1A—C9A—C3A | 120.93 (14) | N1B—C9B—C3B | 120.96 (14) |
C10A—C9A—C3A | 119.19 (14) | C10B—C9B—C3B | 118.90 (15) |
C11A—C10A—C9A | 120.97 (16) | C11B—C10B—C9B | 121.15 (17) |
C11A—C10A—H10A | 119.5 | C11B—C10B—H10B | 119.4 |
C9A—C10A—H10A | 119.5 | C9B—C10B—H10B | 119.4 |
C10A—C11A—C1A | 120.32 (17) | C10B—C11B—C1B | 119.98 (18) |
C10A—C11A—H11A | 119.8 | C10B—C11B—H11B | 120.0 |
C1A—C11A—H11A | 119.8 | C1B—C11B—H11B | 120.0 |
C17A—C12A—C13A | 118.18 (14) | C17B—C12B—C13B | 117.92 (15) |
C17A—C12A—C8A | 119.96 (13) | C17B—C12B—C8B | 120.04 (14) |
C13A—C12A—C8A | 121.86 (13) | C13B—C12B—C8B | 121.97 (14) |
C14A—C13A—C12A | 120.91 (14) | C14B—C13B—C12B | 120.90 (16) |
C14A—C13A—H13A | 119.5 | C14B—C13B—H13B | 119.6 |
C12A—C13A—H13A | 119.5 | C12B—C13B—H13B | 119.6 |
C15A—C14A—C13A | 120.06 (16) | C15B—C14B—C13B | 120.16 (17) |
C15A—C14A—H14A | 120.0 | C15B—C14B—H14B | 119.9 |
C13A—C14A—H14A | 120.0 | C13B—C14B—H14B | 119.9 |
C16A—C15A—C14A | 119.82 (15) | C16B—C15B—C14B | 119.85 (17) |
C16A—C15A—H15A | 120.1 | C16B—C15B—H15B | 120.1 |
C14A—C15A—H15A | 120.1 | C14B—C15B—H15B | 120.1 |
C15A—C16A—C17A | 119.95 (15) | C15B—C16B—C17B | 119.99 (17) |
C15A—C16A—H16 | 120.0 | C15B—C16B—H16B | 120.0 |
C17A—C16A—H16 | 120.0 | C17B—C16B—H16B | 120.0 |
C16A—C17A—C12A | 121.06 (15) | C16B—C17B—C12B | 121.18 (16) |
C16A—C17A—H17A | 119.5 | C16B—C17B—H17B | 119.4 |
C12A—C17A—H17A | 119.5 | C12B—C17B—H17B | 119.4 |
| | | |
C11A—C1A—C2A—C3A | 1.1 (2) | C11B—C1B—C2B—C3B | −0.7 (3) |
C1A—C2A—C3A—C9A | 1.2 (2) | C1B—C2B—C3B—C9B | −2.2 (2) |
C1A—C2A—C3A—C4A | −178.83 (14) | C1B—C2B—C3B—C4B | 177.11 (15) |
C5A—O1A—C4A—C3A | −102.58 (18) | C5B—O1B—C4B—C3B | 90.03 (16) |
C5A—O1A—C4A—C7A | 20.0 (2) | C5B—O1B—C4B—C7B | −32.06 (17) |
C2A—C3A—C4A—O1A | −48.50 (18) | C2B—C3B—C4B—O1B | 44.6 (2) |
C9A—C3A—C4A—O1A | 131.52 (14) | C9B—C3B—C4B—O1B | −136.11 (14) |
C2A—C3A—C4A—C7A | −166.07 (13) | C2B—C3B—C4B—C7B | 162.17 (14) |
C9A—C3A—C4A—C7A | 13.9 (2) | C9B—C3B—C4B—C7B | −18.5 (2) |
C4A—O1A—C5A—C6A | 1.9 (3) | C4B—O1B—C5B—C6B | 12.93 (19) |
O1A—C5A—C6A—C7A | −22.8 (2) | O1B—C5B—C6B—C7B | 11.23 (19) |
C5A—C6A—C7A—C4A | 33.21 (18) | O1B—C4B—C7B—C6B | 37.81 (15) |
C5A—C6A—C7A—C8A | 157.52 (16) | C3B—C4B—C7B—C6B | −84.17 (15) |
O1A—C4A—C7A—C6A | −33.10 (15) | O1B—C4B—C7B—C8B | 163.83 (12) |
C3A—C4A—C7A—C6A | 88.58 (14) | C3B—C4B—C7B—C8B | 41.86 (17) |
O1A—C4A—C7A—C8A | −159.90 (13) | C5B—C6B—C7B—C4B | −29.14 (17) |
C3A—C4A—C7A—C8A | −38.22 (17) | C5B—C6B—C7B—C8B | −152.64 (14) |
C9A—N1A—C8A—C12A | −171.25 (13) | C9B—N1B—C8B—C12B | 167.10 (13) |
C9A—N1A—C8A—C7A | −47.25 (18) | C9B—N1B—C8B—C7B | 43.82 (18) |
C6A—C7A—C8A—N1A | −64.63 (16) | C4B—C7B—C8B—N1B | −53.87 (16) |
C4A—C7A—C8A—N1A | 53.81 (16) | C6B—C7B—C8B—N1B | 63.59 (18) |
C6A—C7A—C8A—C12A | 58.18 (17) | C4B—C7B—C8B—C12B | −176.93 (12) |
C4A—C7A—C8A—C12A | 176.62 (12) | C6B—C7B—C8B—C12B | −59.47 (18) |
C8A—N1A—C9A—C10A | −159.16 (15) | C8B—N1B—C9B—C10B | 162.03 (14) |
C8A—N1A—C9A—C3A | 24.1 (2) | C8B—N1B—C9B—C3B | −21.3 (2) |
C2A—C3A—C9A—N1A | 174.08 (14) | C2B—C3B—C9B—N1B | −173.23 (14) |
C4A—C3A—C9A—N1A | −5.9 (2) | C4B—C3B—C9B—N1B | 7.5 (2) |
C2A—C3A—C9A—C10A | −2.7 (2) | C2B—C3B—C9B—C10B | 3.5 (2) |
C4A—C3A—C9A—C10A | 177.29 (15) | C4B—C3B—C9B—C10B | −175.81 (14) |
N1A—C9A—C10A—C11A | −174.71 (16) | N1B—C9B—C10B—C11B | 174.73 (15) |
C3A—C9A—C10A—C11A | 2.1 (3) | C3B—C9B—C10B—C11B | −2.0 (2) |
C9A—C10A—C11A—C1A | 0.1 (3) | C9B—C10B—C11B—C1B | −0.9 (3) |
C2A—C1A—C11A—C10A | −1.7 (3) | C2B—C1B—C11B—C10B | 2.3 (3) |
N1A—C8A—C12A—C17A | −147.76 (14) | N1B—C8B—C12B—C17B | 144.37 (14) |
C7A—C8A—C12A—C17A | 90.22 (16) | C7B—C8B—C12B—C17B | −93.35 (16) |
N1A—C8A—C12A—C13A | 31.98 (19) | N1B—C8B—C12B—C13B | −38.86 (19) |
C7A—C8A—C12A—C13A | −90.04 (16) | C7B—C8B—C12B—C13B | 83.42 (17) |
C17A—C12A—C13A—C14A | 1.3 (2) | C17B—C12B—C13B—C14B | 0.3 (2) |
C8A—C12A—C13A—C14A | −178.45 (14) | C8B—C12B—C13B—C14B | −176.56 (14) |
C12A—C13A—C14A—C15A | −0.7 (3) | C12B—C13B—C14B—C15B | −0.3 (3) |
C13A—C14A—C15A—C16A | −0.5 (3) | C13B—C14B—C15B—C16B | 0.5 (3) |
C14A—C15A—C16A—C17A | 1.1 (3) | C14B—C15B—C16B—C17B | −0.7 (3) |
C15A—C16A—C17A—C12A | −0.5 (2) | C15B—C16B—C17B—C12B | 0.7 (3) |
C13A—C12A—C17A—C16A | −0.7 (2) | C13B—C12B—C17B—C16B | −0.5 (2) |
C8A—C12A—C17A—C16A | 179.09 (14) | C8B—C12B—C17B—C16B | 176.45 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1BN···O1Ai | 0.844 (19) | 2.23 (2) | 3.0617 (18) | 167.2 (16) |
Symmetry code: (i) x, y+1, z. |
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