The asymmetric unit of the title compound, 4C
17H
17NO·H
2O, contains four independent naphthalenol molecules and one molecule of water. All of the molecules in the asymmetric unit are connected into a contiguous row
via O—H
O hydrogen bonds. This unique hydrogen-bonded row is, in turn, linked to form extended O—H
O hydrogen-bonded chains, through unit-cell translations in the
a direction. The hydrogen-bonding motif also contains an O(water)—H
π(arene) weak hydrogen bond, with an H
Cg distance of 2.64 (4) Å (where
Cg is the center of gravity of the phenyl ring).
Supporting information
CCDC reference: 202361
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.090
- Data-to-parameter ratio = 7.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
PLAT_420 Alert B D-H Without Acceptor O1W - H2W ?
| Author response: The hydogen-bonding
motif also contains an O1W-H2W...\p(arene) weak hydrogen bond.
|
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 26.02
From the CIF: _reflns_number_total 5415
Count of symmetry unique reflns 5422
Completeness (_total/calc) 99.87%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
The title compound was obtained as a colourless oil in 95% yield by treatment of 1,4-dihydro-1,4-epoxynaphthalene with N-methylaniline and catalytic [Rh(cyclooctadiene)Cl]2 and bis-(diphenylphosphino)ferrocene in refluxing tetrahydrofuran. The oil was allowed to stand at room temperature for several weeks during which time suitable crystals of (I) gradually formed.
All H atoms were included in calculated positions, with C—H distances of 0.95 (for sp2), 1.00 (for sp3), 0.98 (for methyl sp3) and 0.84 Å for O—H. They were then included in the refinement in riding-motion approximation, with Uiso = 1.2Ueq (Uiso = 1.5Ueq for methyl) of the carrier atom. The H atoms of the water molecule were located in a difference Fourier map and refined with tight geometric constraints (O—H = 0.8400± 0.0001 Å). Due to the lack of anomalous scatterers, the absolute configuration was not determined from the X-ray diffraction data and Friedel pairs were merged. The enantiomer has been assigned by reference to analogous reactions with an unchanging chiral ligand in the synthetic procedure.
Data collection: COLLECT (Nonius BV, 1997-2002); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(1
R*,2
R*)-2-(Methylphenylamino)-1,2-dihydronaphthalen-1-ol–water (4/1)
top
Crystal data top
4C17H17NO·H2O | Dx = 1.237 Mg m−3 |
Mr = 1023.28 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P31 | Cell parameters from 49468 reflections |
Hall symbol: P 31 | θ = 2.6–26.1° |
a = 12.3595 (1) Å | µ = 0.08 mm−1 |
c = 31.1411 (4) Å | T = 150 K |
V = 4119.71 (7) Å3 | Block, colourless |
Z = 3 | 0.25 × 0.24 × 0.20 mm |
F(000) = 1638 | |
Data collection top
Nonius KappaCCD diffractometer | 4878 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 26.0°, θmin = 2.7° |
Detector resolution: 9 pixels mm-1 | h = −15→15 |
ϕ scans and ω scans with κ offsets | k = −12→15 |
49468 measured reflections | l = −38→38 |
5415 independent reflections | |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.6948P] where P = (Fo2 + 2Fc2)/3 |
5415 reflections | (Δ/σ)max = 0.001 |
708 parameters | Δρmax = 0.19 e Å−3 |
3 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
4C17H17NO·H2O | Z = 3 |
Mr = 1023.28 | Mo Kα radiation |
Trigonal, P31 | µ = 0.08 mm−1 |
a = 12.3595 (1) Å | T = 150 K |
c = 31.1411 (4) Å | 0.25 × 0.24 × 0.20 mm |
V = 4119.71 (7) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 4878 reflections with I > 2σ(I) |
49468 measured reflections | Rint = 0.023 |
5415 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.037 | 3 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.19 e Å−3 |
5415 reflections | Δρmin = −0.22 e Å−3 |
708 parameters | |
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 | |
O1A | 0.13698 (19) | −0.00221 (19) | 0.37733 (6) | 0.0444 (5) | |
H1OA | 0.2070 | 0.0074 | 0.3705 | 0.053* | |
N1A | 0.2851 (2) | 0.1307 (2) | 0.45318 (7) | 0.0385 (5) | |
C1A | 0.1043 (2) | −0.0548 (2) | 0.41909 (8) | 0.0355 (6) | |
H1AB | 0.1450 | −0.1060 | 0.4245 | 0.043* | |
C2A | 0.1484 (2) | 0.0477 (2) | 0.45274 (8) | 0.0358 (6) | |
H2AA | 0.1128 | 0.1014 | 0.4440 | 0.043* | |
C3A | 0.0927 (3) | −0.0048 (3) | 0.49634 (8) | 0.0384 (6) | |
H3AA | 0.1399 | 0.0322 | 0.5216 | 0.046* | |
C4A | −0.0221 (3) | −0.1025 (3) | 0.49933 (9) | 0.0386 (6) | |
H4AA | −0.0557 | −0.1344 | 0.5269 | 0.046* | |
C5A | −0.0980 (3) | −0.1624 (2) | 0.46123 (8) | 0.0343 (6) | |
C6A | −0.2262 (3) | −0.2421 (2) | 0.46269 (9) | 0.0386 (6) | |
H6AA | −0.2683 | −0.2595 | 0.4895 | 0.046* | |
C7A | −0.2936 (3) | −0.2964 (3) | 0.42596 (10) | 0.0449 (7) | |
H7AA | −0.3817 | −0.3490 | 0.4274 | 0.054* | |
C8A | −0.2332 (3) | −0.2744 (3) | 0.38714 (10) | 0.0482 (7) | |
H8AA | −0.2798 | −0.3128 | 0.3619 | 0.058* | |
C9A | −0.1052 (3) | −0.1966 (3) | 0.38464 (9) | 0.0440 (7) | |
H9AA | −0.0643 | −0.1829 | 0.3577 | 0.053* | |
C10A | −0.0356 (2) | −0.1383 (2) | 0.42122 (8) | 0.0346 (6) | |
C11A | 0.3319 (2) | 0.2581 (2) | 0.46307 (8) | 0.0352 (6) | |
C12A | 0.2683 (3) | 0.3205 (3) | 0.45095 (10) | 0.0440 (7) | |
H12A | 0.1934 | 0.2772 | 0.4348 | 0.053* | |
C13A | 0.3125 (3) | 0.4431 (3) | 0.46203 (11) | 0.0516 (8) | |
H13A | 0.2661 | 0.4823 | 0.4541 | 0.062* | |
C14A | 0.4226 (3) | 0.5103 (3) | 0.48435 (11) | 0.0554 (8) | |
H14A | 0.4515 | 0.5945 | 0.4924 | 0.067* | |
C15A | 0.4900 (3) | 0.4526 (3) | 0.49472 (10) | 0.0523 (8) | |
H15A | 0.5678 | 0.4986 | 0.5091 | 0.063* | |
C16A | 0.4456 (3) | 0.3283 (3) | 0.48442 (9) | 0.0439 (7) | |
H16A | 0.4933 | 0.2902 | 0.4920 | 0.053* | |
C17A | 0.3563 (3) | 0.0740 (3) | 0.46843 (11) | 0.0495 (7) | |
H17A | 0.4418 | 0.1209 | 0.4573 | 0.074* | |
H17B | 0.3168 | −0.0126 | 0.4584 | 0.074* | |
H17C | 0.3583 | 0.0756 | 0.4999 | 0.074* | |
O1B | −0.39625 (19) | 0.17881 (19) | 0.34990 (6) | 0.0438 (5) | |
H1OB | −0.3566 | 0.1400 | 0.3487 | 0.053* | |
N1B | −0.35436 (18) | 0.10527 (19) | 0.26670 (8) | 0.0366 (5) | |
C1B | −0.3642 (2) | 0.2603 (2) | 0.31394 (8) | 0.0316 (5) | |
H1BB | −0.2714 | 0.3159 | 0.3132 | 0.038* | |
C2B | −0.4061 (2) | 0.1873 (2) | 0.27192 (8) | 0.0297 (5) | |
H2BA | −0.4990 | 0.1327 | 0.2736 | 0.036* | |
C3B | −0.3795 (2) | 0.2763 (3) | 0.23495 (8) | 0.0375 (6) | |
H3BA | −0.3539 | 0.2606 | 0.2080 | 0.045* | |
C4B | −0.3915 (2) | 0.3752 (3) | 0.23993 (9) | 0.0385 (6) | |
H4BA | −0.3743 | 0.4307 | 0.2165 | 0.046* | |
C5B | −0.4314 (2) | 0.4012 (2) | 0.28121 (8) | 0.0329 (5) | |
C6B | −0.4824 (3) | 0.4793 (2) | 0.28404 (10) | 0.0437 (7) | |
H6BA | −0.4863 | 0.5218 | 0.2592 | 0.052* | |
C7B | −0.5276 (3) | 0.4955 (3) | 0.32281 (12) | 0.0509 (8) | |
H7BA | −0.5627 | 0.5484 | 0.3244 | 0.061* | |
C8B | −0.5214 (3) | 0.4346 (3) | 0.35905 (11) | 0.0487 (7) | |
H8BA | −0.5531 | 0.4450 | 0.3856 | 0.058* | |
C9B | −0.4689 (3) | 0.3581 (2) | 0.35679 (9) | 0.0398 (6) | |
H9BA | −0.4639 | 0.3173 | 0.3819 | 0.048* | |
C10B | −0.4244 (2) | 0.3408 (2) | 0.31855 (8) | 0.0311 (5) | |
C11B | −0.4283 (2) | −0.0205 (2) | 0.25704 (8) | 0.0319 (5) | |
C12B | −0.5585 (2) | −0.0845 (2) | 0.26197 (10) | 0.0418 (6) | |
H12B | −0.5987 | −0.0408 | 0.2720 | 0.050* | |
C13B | −0.6289 (3) | −0.2097 (3) | 0.25257 (11) | 0.0523 (8) | |
H13B | −0.7170 | −0.2506 | 0.2562 | 0.063* | |
C14B | −0.5754 (3) | −0.2776 (3) | 0.23803 (11) | 0.0548 (8) | |
H14B | −0.6251 | −0.3640 | 0.2317 | 0.066* | |
C15B | −0.4484 (3) | −0.2164 (3) | 0.23307 (10) | 0.0495 (7) | |
H15B | −0.4098 | −0.2613 | 0.2228 | 0.059* | |
C16B | −0.3747 (3) | −0.0904 (3) | 0.24260 (9) | 0.0392 (6) | |
H16B | −0.2866 | −0.0511 | 0.2393 | 0.047* | |
C17B | −0.2215 (3) | 0.1660 (3) | 0.25810 (12) | 0.0502 (8) | |
H17D | −0.1838 | 0.1283 | 0.2760 | 0.075* | |
H17E | −0.1827 | 0.2552 | 0.2647 | 0.075* | |
H17F | −0.2080 | 0.1554 | 0.2277 | 0.075* | |
O1C | −0.26497 (19) | 0.04666 (18) | 0.36884 (6) | 0.0405 (4) | |
H1OC | −0.1865 | 0.0871 | 0.3694 | 0.049* | |
N1C | −0.16897 (19) | 0.18273 (19) | 0.44974 (7) | 0.0320 (4) | |
C1C | −0.3112 (2) | −0.0104 (2) | 0.40969 (8) | 0.0327 (5) | |
H1CB | −0.2618 | −0.0496 | 0.4196 | 0.039* | |
C2C | −0.2990 (2) | 0.0862 (2) | 0.44294 (8) | 0.0289 (5) | |
H2CA | −0.3428 | 0.1289 | 0.4309 | 0.035* | |
C3C | −0.3653 (2) | 0.0240 (2) | 0.48399 (8) | 0.0361 (6) | |
H3CA | −0.3314 | 0.0634 | 0.5108 | 0.043* | |
C4C | −0.4698 (3) | −0.0846 (3) | 0.48315 (9) | 0.0419 (6) | |
H4CA | −0.5114 | −0.1220 | 0.5093 | 0.050* | |
C5C | −0.5224 (3) | −0.1483 (2) | 0.44242 (9) | 0.0400 (6) | |
C6C | −0.6476 (3) | −0.2433 (3) | 0.43987 (12) | 0.0538 (8) | |
H6CA | −0.6984 | −0.2683 | 0.4649 | 0.065* | |
C7C | −0.6973 (3) | −0.3006 (3) | 0.40108 (14) | 0.0624 (10) | |
H7CA | −0.7825 | −0.3642 | 0.3994 | 0.075* | |
C8C | −0.6237 (3) | −0.2658 (3) | 0.36491 (13) | 0.0589 (9) | |
H8CA | −0.6585 | −0.3062 | 0.3384 | 0.071* | |
C9C | −0.4977 (3) | −0.1713 (3) | 0.36674 (10) | 0.0480 (7) | |
H9CA | −0.4473 | −0.1487 | 0.3417 | 0.058* | |
C10C | −0.4474 (3) | −0.1114 (2) | 0.40520 (9) | 0.0370 (6) | |
C11C | −0.1408 (2) | 0.3057 (2) | 0.45853 (8) | 0.0308 (5) | |
C12C | −0.2189 (3) | 0.3517 (2) | 0.44568 (9) | 0.0378 (6) | |
H12C | −0.2964 | 0.2972 | 0.4321 | 0.045* | |
C13C | −0.1845 (3) | 0.4760 (3) | 0.45249 (10) | 0.0459 (7) | |
H13C | −0.2389 | 0.5053 | 0.4436 | 0.055* | |
C14C | −0.0723 (3) | 0.5577 (3) | 0.47203 (10) | 0.0463 (7) | |
H14C | −0.0490 | 0.6427 | 0.4763 | 0.056* | |
C15C | 0.0049 (3) | 0.5137 (3) | 0.48512 (9) | 0.0436 (7) | |
H15C | 0.0823 | 0.5690 | 0.4985 | 0.052* | |
C16C | −0.0288 (2) | 0.3896 (2) | 0.47901 (9) | 0.0361 (6) | |
H16C | 0.0252 | 0.3609 | 0.4889 | 0.043* | |
C17C | −0.0935 (3) | 0.1392 (3) | 0.47167 (10) | 0.0422 (6) | |
H17G | −0.0056 | 0.1922 | 0.4636 | 0.063* | |
H17H | −0.1219 | 0.0526 | 0.4633 | 0.063* | |
H17I | −0.1024 | 0.1435 | 0.5028 | 0.063* | |
O1D | 0.02106 (18) | 0.13985 (17) | 0.35565 (6) | 0.0389 (4) | |
H1OD | 0.0435 | 0.0862 | 0.3579 | 0.047* | |
N1D | 0.12773 (18) | 0.08079 (19) | 0.28108 (7) | 0.0326 (5) | |
C1D | 0.0976 (2) | 0.2314 (2) | 0.32460 (8) | 0.0301 (5) | |
H1DB | 0.1869 | 0.2691 | 0.3337 | 0.036* | |
C2D | 0.0826 (2) | 0.1697 (2) | 0.28051 (8) | 0.0285 (5) | |
H2DA | −0.0091 | 0.1207 | 0.2744 | 0.034* | |
C3D | 0.1405 (2) | 0.2661 (2) | 0.24550 (8) | 0.0347 (6) | |
H3DA | 0.1765 | 0.2492 | 0.2213 | 0.042* | |
C4D | 0.1421 (2) | 0.3737 (2) | 0.24791 (8) | 0.0365 (6) | |
H4DA | 0.1769 | 0.4316 | 0.2249 | 0.044* | |
C5D | 0.0914 (2) | 0.4054 (2) | 0.28525 (8) | 0.0311 (5) | |
C6D | 0.0654 (3) | 0.5027 (2) | 0.28385 (9) | 0.0388 (6) | |
H6DA | 0.0832 | 0.5514 | 0.2585 | 0.047* | |
C7D | 0.0138 (3) | 0.5294 (2) | 0.31905 (10) | 0.0421 (6) | |
H7DA | −0.0039 | 0.5958 | 0.3178 | 0.051* | |
C8D | −0.0115 (3) | 0.4588 (3) | 0.35580 (9) | 0.0410 (6) | |
H8DA | −0.0464 | 0.4772 | 0.3800 | 0.049* | |
C9D | 0.0135 (2) | 0.3613 (2) | 0.35792 (8) | 0.0348 (6) | |
H9DA | −0.0044 | 0.3134 | 0.3835 | 0.042* | |
C10D | 0.0644 (2) | 0.3335 (2) | 0.32295 (8) | 0.0291 (5) | |
C11D | 0.0489 (2) | −0.0440 (2) | 0.27010 (8) | 0.0297 (5) | |
C12D | −0.0789 (2) | −0.1058 (2) | 0.27971 (8) | 0.0345 (5) | |
H12D | −0.1141 | −0.0611 | 0.2929 | 0.041* | |
C13D | −0.1544 (3) | −0.2312 (3) | 0.27027 (9) | 0.0432 (7) | |
H13D | −0.2408 | −0.2714 | 0.2771 | 0.052* | |
C14D | −0.1067 (3) | −0.2990 (3) | 0.25108 (10) | 0.0484 (7) | |
H14D | −0.1592 | −0.3853 | 0.2450 | 0.058* | |
C15D | 0.0191 (3) | −0.2390 (3) | 0.24091 (10) | 0.0484 (7) | |
H15D | 0.0527 | −0.2846 | 0.2273 | 0.058* | |
C16D | 0.0969 (3) | −0.1136 (3) | 0.25027 (9) | 0.0389 (6) | |
H16D | 0.1832 | −0.0744 | 0.2433 | 0.047* | |
C17D | 0.2622 (2) | 0.1335 (3) | 0.27839 (9) | 0.0380 (6) | |
H17J | 0.2857 | 0.0780 | 0.2930 | 0.057* | |
H17K | 0.3041 | 0.2157 | 0.2922 | 0.057* | |
H17L | 0.2873 | 0.1422 | 0.2482 | 0.057* | |
O1W | −0.64623 (19) | 0.00001 (19) | 0.36067 (9) | 0.0626 (6) | |
H1W | −0.5739 | 0.062 | 0.3590 | 0.075* | |
H2W | −0.647 | −0.0680 | 0.3625 | 0.075* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0424 (11) | 0.0559 (12) | 0.0363 (10) | 0.0256 (10) | 0.0058 (8) | 0.0110 (9) |
N1A | 0.0367 (12) | 0.0378 (12) | 0.0479 (13) | 0.0239 (10) | −0.0007 (10) | −0.0009 (10) |
C1A | 0.0399 (14) | 0.0372 (14) | 0.0334 (14) | 0.0225 (12) | 0.0015 (11) | 0.0030 (11) |
C2A | 0.0322 (13) | 0.0358 (14) | 0.0428 (15) | 0.0196 (12) | −0.0032 (11) | 0.0006 (11) |
C3A | 0.0408 (15) | 0.0410 (15) | 0.0336 (14) | 0.0205 (13) | −0.0052 (11) | −0.0019 (11) |
C4A | 0.0505 (16) | 0.0403 (15) | 0.0328 (14) | 0.0284 (14) | 0.0009 (12) | 0.0034 (11) |
C5A | 0.0480 (15) | 0.0251 (12) | 0.0343 (14) | 0.0216 (12) | −0.0001 (11) | 0.0030 (10) |
C6A | 0.0409 (15) | 0.0295 (13) | 0.0463 (16) | 0.0183 (12) | 0.0060 (12) | 0.0067 (11) |
C7A | 0.0443 (16) | 0.0327 (14) | 0.0519 (17) | 0.0149 (12) | −0.0020 (13) | 0.0042 (12) |
C8A | 0.0495 (17) | 0.0430 (16) | 0.0403 (16) | 0.0142 (14) | −0.0074 (13) | −0.0017 (13) |
C9A | 0.0461 (16) | 0.0457 (16) | 0.0324 (14) | 0.0171 (14) | −0.0029 (12) | 0.0020 (12) |
C10A | 0.0403 (14) | 0.0276 (12) | 0.0377 (14) | 0.0181 (11) | 0.0028 (11) | 0.0063 (10) |
C11A | 0.0351 (14) | 0.0349 (14) | 0.0358 (14) | 0.0176 (12) | 0.0085 (11) | 0.0050 (11) |
C12A | 0.0340 (14) | 0.0345 (15) | 0.0610 (19) | 0.0154 (12) | 0.0064 (13) | 0.0049 (13) |
C13A | 0.0415 (17) | 0.0338 (15) | 0.078 (2) | 0.0178 (13) | 0.0167 (15) | 0.0116 (14) |
C14A | 0.0545 (19) | 0.0295 (14) | 0.069 (2) | 0.0107 (14) | 0.0173 (16) | 0.0038 (14) |
C15A | 0.0424 (16) | 0.0437 (17) | 0.0515 (18) | 0.0069 (14) | 0.0052 (13) | 0.0040 (14) |
C16A | 0.0356 (14) | 0.0441 (16) | 0.0473 (17) | 0.0164 (13) | 0.0044 (12) | 0.0075 (13) |
C17A | 0.0486 (17) | 0.0460 (17) | 0.0645 (19) | 0.0317 (14) | −0.0106 (14) | −0.0050 (14) |
O1B | 0.0575 (12) | 0.0494 (12) | 0.0373 (10) | 0.0363 (10) | 0.0023 (9) | 0.0079 (8) |
N1B | 0.0236 (10) | 0.0329 (11) | 0.0559 (14) | 0.0161 (9) | −0.0025 (9) | −0.0088 (10) |
C1B | 0.0300 (12) | 0.0310 (12) | 0.0337 (13) | 0.0153 (11) | −0.0041 (10) | −0.0010 (10) |
C2B | 0.0217 (11) | 0.0286 (12) | 0.0395 (14) | 0.0130 (10) | −0.0031 (10) | −0.0045 (10) |
C3B | 0.0361 (14) | 0.0440 (15) | 0.0325 (14) | 0.0202 (12) | −0.0002 (11) | −0.0039 (11) |
C4B | 0.0356 (14) | 0.0382 (14) | 0.0381 (14) | 0.0157 (12) | 0.0033 (11) | 0.0099 (11) |
C5B | 0.0240 (11) | 0.0236 (12) | 0.0432 (14) | 0.0061 (10) | −0.0032 (10) | −0.0003 (10) |
C6B | 0.0375 (15) | 0.0282 (13) | 0.0645 (19) | 0.0159 (12) | −0.0035 (13) | 0.0038 (13) |
C7B | 0.0406 (16) | 0.0321 (14) | 0.084 (2) | 0.0212 (13) | 0.0028 (15) | −0.0091 (15) |
C8B | 0.0455 (17) | 0.0413 (16) | 0.0561 (19) | 0.0193 (14) | 0.0072 (14) | −0.0142 (14) |
C9B | 0.0401 (14) | 0.0355 (14) | 0.0399 (15) | 0.0158 (12) | −0.0021 (12) | −0.0063 (11) |
C10B | 0.0268 (12) | 0.0246 (12) | 0.0380 (14) | 0.0099 (10) | −0.0024 (10) | −0.0029 (10) |
C11B | 0.0337 (13) | 0.0319 (13) | 0.0330 (13) | 0.0186 (11) | −0.0005 (10) | −0.0020 (10) |
C12B | 0.0330 (14) | 0.0317 (14) | 0.0604 (18) | 0.0159 (12) | 0.0040 (12) | −0.0062 (12) |
C13B | 0.0386 (15) | 0.0351 (15) | 0.074 (2) | 0.0115 (13) | 0.0066 (14) | −0.0086 (14) |
C14B | 0.0560 (19) | 0.0285 (14) | 0.073 (2) | 0.0162 (14) | 0.0041 (16) | −0.0093 (14) |
C15B | 0.0592 (19) | 0.0415 (16) | 0.0612 (19) | 0.0351 (15) | 0.0045 (15) | −0.0017 (14) |
C16B | 0.0391 (15) | 0.0399 (15) | 0.0459 (16) | 0.0250 (13) | −0.0006 (12) | −0.0008 (12) |
C17B | 0.0253 (13) | 0.0433 (16) | 0.081 (2) | 0.0162 (12) | −0.0035 (13) | −0.0166 (15) |
O1C | 0.0470 (11) | 0.0452 (11) | 0.0329 (9) | 0.0257 (10) | 0.0030 (8) | 0.0032 (8) |
N1C | 0.0299 (11) | 0.0285 (10) | 0.0418 (12) | 0.0178 (9) | −0.0017 (9) | −0.0011 (9) |
C1C | 0.0398 (14) | 0.0339 (13) | 0.0304 (13) | 0.0229 (11) | 0.0003 (11) | 0.0034 (10) |
C2C | 0.0295 (12) | 0.0283 (12) | 0.0330 (13) | 0.0175 (10) | −0.0019 (10) | 0.0006 (10) |
C3C | 0.0376 (14) | 0.0382 (14) | 0.0336 (13) | 0.0198 (12) | 0.0002 (11) | −0.0007 (11) |
C4C | 0.0406 (15) | 0.0434 (16) | 0.0401 (15) | 0.0197 (13) | 0.0062 (12) | 0.0089 (12) |
C5C | 0.0396 (15) | 0.0278 (13) | 0.0533 (17) | 0.0172 (12) | −0.0018 (12) | 0.0075 (11) |
C6C | 0.0431 (17) | 0.0355 (15) | 0.074 (2) | 0.0129 (14) | −0.0031 (15) | 0.0090 (15) |
C7C | 0.0481 (19) | 0.0326 (16) | 0.096 (3) | 0.0121 (14) | −0.0215 (19) | 0.0022 (17) |
C8C | 0.069 (2) | 0.0379 (16) | 0.072 (2) | 0.0283 (16) | −0.0359 (19) | −0.0157 (16) |
C9C | 0.0609 (19) | 0.0387 (15) | 0.0504 (17) | 0.0294 (15) | −0.0162 (14) | −0.0083 (13) |
C10C | 0.0432 (15) | 0.0266 (12) | 0.0470 (16) | 0.0216 (11) | −0.0083 (12) | −0.0008 (11) |
C11C | 0.0373 (14) | 0.0293 (12) | 0.0286 (12) | 0.0188 (11) | 0.0055 (10) | 0.0017 (10) |
C12C | 0.0443 (15) | 0.0345 (14) | 0.0416 (14) | 0.0251 (12) | −0.0033 (12) | −0.0016 (11) |
C13C | 0.0609 (19) | 0.0394 (16) | 0.0488 (17) | 0.0336 (15) | 0.0057 (14) | 0.0051 (13) |
C14C | 0.0603 (19) | 0.0281 (14) | 0.0498 (17) | 0.0214 (14) | 0.0107 (14) | 0.0014 (12) |
C15C | 0.0457 (16) | 0.0331 (14) | 0.0436 (16) | 0.0135 (13) | 0.0069 (12) | −0.0034 (12) |
C16C | 0.0348 (14) | 0.0337 (14) | 0.0401 (14) | 0.0173 (11) | 0.0057 (11) | 0.0008 (11) |
C17C | 0.0340 (14) | 0.0357 (14) | 0.0631 (18) | 0.0222 (12) | −0.0091 (13) | −0.0049 (13) |
O1D | 0.0498 (11) | 0.0362 (10) | 0.0363 (10) | 0.0258 (9) | 0.0102 (8) | 0.0090 (8) |
N1D | 0.0242 (10) | 0.0302 (11) | 0.0433 (12) | 0.0137 (9) | −0.0034 (9) | −0.0056 (9) |
C1D | 0.0287 (12) | 0.0294 (12) | 0.0296 (12) | 0.0126 (10) | 0.0021 (10) | 0.0043 (10) |
C2D | 0.0232 (11) | 0.0288 (12) | 0.0341 (13) | 0.0135 (10) | −0.0005 (9) | 0.0000 (10) |
C3D | 0.0341 (13) | 0.0427 (15) | 0.0276 (13) | 0.0193 (12) | 0.0027 (10) | −0.0004 (11) |
C4D | 0.0343 (13) | 0.0364 (14) | 0.0324 (13) | 0.0129 (11) | 0.0043 (11) | 0.0057 (11) |
C5D | 0.0242 (12) | 0.0259 (12) | 0.0354 (13) | 0.0066 (10) | −0.0009 (10) | 0.0009 (10) |
C6D | 0.0398 (15) | 0.0280 (13) | 0.0444 (15) | 0.0138 (12) | −0.0027 (12) | 0.0047 (11) |
C7D | 0.0424 (15) | 0.0277 (13) | 0.0567 (17) | 0.0178 (12) | −0.0038 (13) | −0.0036 (12) |
C8D | 0.0403 (15) | 0.0365 (15) | 0.0464 (16) | 0.0194 (12) | 0.0027 (12) | −0.0054 (12) |
C9D | 0.0384 (14) | 0.0312 (13) | 0.0305 (13) | 0.0143 (11) | 0.0017 (11) | −0.0013 (10) |
C10D | 0.0248 (11) | 0.0235 (11) | 0.0343 (13) | 0.0086 (10) | −0.0039 (10) | −0.0030 (10) |
C11D | 0.0289 (12) | 0.0286 (12) | 0.0293 (12) | 0.0126 (10) | −0.0054 (10) | 0.0003 (10) |
C12D | 0.0336 (13) | 0.0324 (13) | 0.0325 (13) | 0.0129 (11) | −0.0025 (10) | −0.0004 (10) |
C13D | 0.0404 (15) | 0.0383 (15) | 0.0344 (14) | 0.0073 (13) | −0.0066 (12) | 0.0049 (11) |
C14D | 0.061 (2) | 0.0284 (14) | 0.0497 (17) | 0.0172 (14) | −0.0181 (14) | −0.0013 (12) |
C15D | 0.065 (2) | 0.0374 (15) | 0.0525 (17) | 0.0331 (15) | −0.0188 (15) | −0.0086 (13) |
C16D | 0.0414 (15) | 0.0396 (15) | 0.0410 (15) | 0.0243 (13) | −0.0096 (12) | −0.0044 (12) |
C17D | 0.0245 (13) | 0.0409 (15) | 0.0496 (16) | 0.0170 (12) | −0.0019 (11) | −0.0052 (12) |
O1W | 0.0534 (13) | 0.0579 (15) | 0.0844 (16) | 0.0338 (12) | 0.0131 (13) | 0.0104 (13) |
Geometric parameters (Å, º) top
O1A—C1A | 1.419 (3) | O1C—H1OC | 0.8400 |
O1A—H1OA | 0.8400 | N1C—C11C | 1.405 (3) |
N1A—C11A | 1.413 (3) | N1C—C17C | 1.458 (3) |
N1A—C17A | 1.452 (3) | N1C—C2C | 1.461 (3) |
N1A—C2A | 1.474 (3) | C1C—C10C | 1.520 (4) |
C1A—C10A | 1.508 (4) | C1C—C2C | 1.530 (3) |
C1A—C2A | 1.520 (4) | C1C—H1CB | 1.0000 |
C1A—H1AB | 1.0000 | C2C—C3C | 1.506 (3) |
C2A—C3A | 1.514 (4) | C2C—H2CA | 1.0000 |
C2A—H2AA | 1.0000 | C3C—C4C | 1.318 (4) |
C3A—C4A | 1.330 (4) | C3C—H3CA | 0.9500 |
C3A—H3AA | 0.9500 | C4C—C5C | 1.462 (4) |
C4A—C5A | 1.463 (4) | C4C—H4CA | 0.9500 |
C4A—H4AA | 0.9500 | C5C—C6C | 1.402 (4) |
C5A—C6A | 1.387 (4) | C5C—C10C | 1.410 (4) |
C5A—C10A | 1.416 (4) | C6C—C7C | 1.379 (5) |
C6A—C7A | 1.376 (4) | C6C—H6CA | 0.9500 |
C6A—H6AA | 0.9500 | C7C—C8C | 1.374 (6) |
C7A—C8A | 1.374 (4) | C7C—H7CA | 0.9500 |
C7A—H7AA | 0.9500 | C8C—C9C | 1.405 (5) |
C8A—C9A | 1.384 (4) | C8C—H8CA | 0.9500 |
C8A—H8AA | 0.9500 | C9C—C10C | 1.381 (4) |
C9A—C10A | 1.392 (4) | C9C—H9CA | 0.9500 |
C9A—H9AA | 0.9500 | C11C—C16C | 1.401 (4) |
C11A—C16A | 1.396 (4) | C11C—C12C | 1.402 (4) |
C11A—C12A | 1.400 (4) | C12C—C13C | 1.390 (4) |
C12A—C13A | 1.374 (4) | C12C—H12C | 0.9500 |
C12A—H12A | 0.9500 | C13C—C14C | 1.383 (5) |
C13A—C14A | 1.377 (5) | C13C—H13C | 0.9500 |
C13A—H13A | 0.9500 | C14C—C15C | 1.376 (4) |
C14A—C15A | 1.378 (5) | C14C—H14C | 0.9500 |
C14A—H14A | 0.9500 | C15C—C16C | 1.387 (4) |
C15A—C16A | 1.386 (4) | C15C—H15C | 0.9500 |
C15A—H15A | 0.9500 | C16C—H16C | 0.9500 |
C16A—H16A | 0.9500 | C17C—H17G | 0.9800 |
C17A—H17A | 0.9800 | C17C—H17H | 0.9800 |
C17A—H17B | 0.9800 | C17C—H17I | 0.9800 |
C17A—H17C | 0.9800 | O1D—C1D | 1.428 (3) |
O1B—C1B | 1.423 (3) | O1D—H1OD | 0.8400 |
O1B—H1OB | 0.8400 | N1D—C11D | 1.394 (3) |
N1B—C11B | 1.386 (3) | N1D—C17D | 1.452 (3) |
N1B—C17B | 1.449 (3) | N1D—C2D | 1.461 (3) |
N1B—C2B | 1.454 (3) | C1D—C10D | 1.511 (3) |
C1B—C10B | 1.518 (3) | C1D—C2D | 1.536 (3) |
C1B—C2B | 1.525 (3) | C1D—H1DB | 1.0000 |
C1B—H1BB | 1.0000 | C2D—C3D | 1.505 (3) |
C2B—C3B | 1.510 (4) | C2D—H2DA | 1.0000 |
C2B—H2BA | 1.0000 | C3D—C4D | 1.322 (4) |
C3B—C4B | 1.313 (4) | C3D—H3DA | 0.9500 |
C3B—H3BA | 0.9500 | C4D—C5D | 1.464 (4) |
C4B—C5B | 1.468 (4) | C4D—H4DA | 0.9500 |
C4B—H4BA | 0.9500 | C5D—C6D | 1.393 (4) |
C5B—C6B | 1.396 (4) | C5D—C10D | 1.408 (3) |
C5B—C10B | 1.408 (4) | C6D—C7D | 1.388 (4) |
C6B—C7B | 1.386 (4) | C6D—H6DA | 0.9500 |
C6B—H6BA | 0.9500 | C7D—C8D | 1.376 (4) |
C7B—C8B | 1.379 (5) | C7D—H7DA | 0.9500 |
C7B—H7BA | 0.9500 | C8D—C9D | 1.387 (4) |
C8B—C9B | 1.391 (4) | C8D—H8DA | 0.9500 |
C8B—H8BA | 0.9500 | C9D—C10D | 1.385 (4) |
C9B—C10B | 1.373 (4) | C9D—H9DA | 0.9500 |
C9B—H9BA | 0.9500 | C11D—C12D | 1.400 (3) |
C11B—C16B | 1.401 (4) | C11D—C16D | 1.409 (4) |
C11B—C12B | 1.403 (4) | C12D—C13D | 1.383 (4) |
C12B—C13B | 1.375 (4) | C12D—H12D | 0.9500 |
C12B—H12B | 0.9500 | C13D—C14D | 1.378 (5) |
C13B—C14B | 1.379 (4) | C13D—H13D | 0.9500 |
C13B—H13B | 0.9500 | C14D—C15D | 1.384 (5) |
C14B—C15B | 1.368 (5) | C14D—H14D | 0.9500 |
C14B—H14B | 0.9500 | C15D—C16D | 1.386 (4) |
C15B—C16B | 1.386 (4) | C15D—H15D | 0.9500 |
C15B—H15B | 0.9500 | C16D—H16D | 0.9500 |
C16B—H16B | 0.9500 | C17D—H17J | 0.9800 |
C17B—H17D | 0.9800 | C17D—H17K | 0.9800 |
C17B—H17E | 0.9800 | C17D—H17L | 0.9800 |
C17B—H17F | 0.9800 | O1W—H1W | 0.8400 |
O1C—C1C | 1.428 (3) | O1W—H2W | 0.8400 |
| | | |
C1A—O1A—H1OA | 109.5 | C11C—N1C—C17C | 116.7 (2) |
C11A—N1A—C17A | 117.2 (2) | C11C—N1C—C2C | 119.21 (19) |
C11A—N1A—C2A | 117.8 (2) | C17C—N1C—C2C | 114.3 (2) |
C17A—N1A—C2A | 115.3 (2) | O1C—C1C—C10C | 109.2 (2) |
O1A—C1A—C10A | 108.7 (2) | O1C—C1C—C2C | 111.0 (2) |
O1A—C1A—C2A | 110.4 (2) | C10C—C1C—C2C | 109.9 (2) |
C10A—C1A—C2A | 110.6 (2) | O1C—C1C—H1CB | 108.9 |
O1A—C1A—H1AB | 109.1 | C10C—C1C—H1CB | 108.9 |
C10A—C1A—H1AB | 109.1 | C2C—C1C—H1CB | 108.9 |
C2A—C1A—H1AB | 109.1 | N1C—C2C—C3C | 112.9 (2) |
N1A—C2A—C3A | 114.0 (2) | N1C—C2C—C1C | 112.01 (19) |
N1A—C2A—C1A | 113.3 (2) | C3C—C2C—C1C | 111.1 (2) |
C3A—C2A—C1A | 111.4 (2) | N1C—C2C—H2CA | 106.8 |
N1A—C2A—H2AA | 105.8 | C3C—C2C—H2CA | 106.8 |
C3A—C2A—H2AA | 105.8 | C1C—C2C—H2CA | 106.8 |
C1A—C2A—H2AA | 105.8 | C4C—C3C—C2C | 120.6 (2) |
C4A—C3A—C2A | 120.1 (2) | C4C—C3C—H3CA | 119.7 |
C4A—C3A—H3AA | 119.9 | C2C—C3C—H3CA | 119.7 |
C2A—C3A—H3AA | 119.9 | C3C—C4C—C5C | 120.7 (2) |
C3A—C4A—C5A | 121.7 (2) | C3C—C4C—H4CA | 119.6 |
C3A—C4A—H4AA | 119.1 | C5C—C4C—H4CA | 119.6 |
C5A—C4A—H4AA | 119.1 | C6C—C5C—C10C | 119.8 (3) |
C6A—C5A—C10A | 119.1 (2) | C6C—C5C—C4C | 120.5 (3) |
C6A—C5A—C4A | 123.3 (2) | C10C—C5C—C4C | 119.7 (2) |
C10A—C5A—C4A | 117.6 (2) | C7C—C6C—C5C | 120.1 (3) |
C7A—C6A—C5A | 121.1 (3) | C7C—C6C—H6CA | 120.0 |
C7A—C6A—H6AA | 119.4 | C5C—C6C—H6CA | 120.0 |
C5A—C6A—H6AA | 119.4 | C8C—C7C—C6C | 120.2 (3) |
C8A—C7A—C6A | 119.9 (3) | C8C—C7C—H7CA | 119.9 |
C8A—C7A—H7AA | 120.0 | C6C—C7C—H7CA | 119.9 |
C6A—C7A—H7AA | 120.0 | C7C—C8C—C9C | 120.8 (3) |
C7A—C8A—C9A | 120.4 (3) | C7C—C8C—H8CA | 119.6 |
C7A—C8A—H8AA | 119.8 | C9C—C8C—H8CA | 119.6 |
C9A—C8A—H8AA | 119.8 | C10C—C9C—C8C | 119.7 (3) |
C8A—C9A—C10A | 120.6 (3) | C10C—C9C—H9CA | 120.1 |
C8A—C9A—H9AA | 119.7 | C8C—C9C—H9CA | 120.1 |
C10A—C9A—H9AA | 119.7 | C9C—C10C—C5C | 119.5 (3) |
C9A—C10A—C5A | 118.7 (2) | C9C—C10C—C1C | 122.5 (3) |
C9A—C10A—C1A | 121.2 (2) | C5C—C10C—C1C | 118.0 (2) |
C5A—C10A—C1A | 120.0 (2) | C16C—C11C—C12C | 117.1 (2) |
C16A—C11A—C12A | 117.0 (3) | C16C—C11C—N1C | 120.6 (2) |
C16A—C11A—N1A | 121.4 (2) | C12C—C11C—N1C | 122.3 (2) |
C12A—C11A—N1A | 121.6 (2) | C13C—C12C—C11C | 120.8 (3) |
C13A—C12A—C11A | 121.1 (3) | C13C—C12C—H12C | 119.6 |
C13A—C12A—H12A | 119.4 | C11C—C12C—H12C | 119.6 |
C11A—C12A—H12A | 119.4 | C14C—C13C—C12C | 121.0 (3) |
C12A—C13A—C14A | 121.3 (3) | C14C—C13C—H13C | 119.5 |
C12A—C13A—H13A | 119.3 | C12C—C13C—H13C | 119.5 |
C14A—C13A—H13A | 119.3 | C15C—C14C—C13C | 118.9 (3) |
C13A—C14A—C15A | 118.5 (3) | C15C—C14C—H14C | 120.6 |
C13A—C14A—H14A | 120.7 | C13C—C14C—H14C | 120.6 |
C15A—C14A—H14A | 120.7 | C14C—C15C—C16C | 120.8 (3) |
C14A—C15A—C16A | 120.8 (3) | C14C—C15C—H15C | 119.6 |
C14A—C15A—H15A | 119.6 | C16C—C15C—H15C | 119.6 |
C16A—C15A—H15A | 119.6 | C15C—C16C—C11C | 121.4 (3) |
C15A—C16A—C11A | 121.1 (3) | C15C—C16C—H16C | 119.3 |
C15A—C16A—H16A | 119.4 | C11C—C16C—H16C | 119.3 |
C11A—C16A—H16A | 119.4 | N1C—C17C—H17G | 109.5 |
N1A—C17A—H17A | 109.5 | N1C—C17C—H17H | 109.5 |
N1A—C17A—H17B | 109.5 | H17G—C17C—H17H | 109.5 |
H17A—C17A—H17B | 109.5 | N1C—C17C—H17I | 109.5 |
N1A—C17A—H17C | 109.5 | H17G—C17C—H17I | 109.5 |
H17A—C17A—H17C | 109.5 | H17H—C17C—H17I | 109.5 |
H17B—C17A—H17C | 109.5 | C1D—O1D—H1OD | 109.5 |
C1B—O1B—H1OB | 109.5 | C11D—N1D—C17D | 119.5 (2) |
C11B—N1B—C17B | 118.8 (2) | C11D—N1D—C2D | 120.73 (19) |
C11B—N1B—C2B | 122.22 (19) | C17D—N1D—C2D | 116.4 (2) |
C17B—N1B—C2B | 116.1 (2) | O1D—C1D—C10D | 109.61 (19) |
O1B—C1B—C10B | 109.6 (2) | O1D—C1D—C2D | 110.15 (19) |
O1B—C1B—C2B | 111.4 (2) | C10D—C1D—C2D | 111.6 (2) |
C10B—C1B—C2B | 109.63 (19) | O1D—C1D—H1DB | 108.5 |
O1B—C1B—H1BB | 108.7 | C10D—C1D—H1DB | 108.5 |
C10B—C1B—H1BB | 108.7 | C2D—C1D—H1DB | 108.5 |
C2B—C1B—H1BB | 108.7 | N1D—C2D—C3D | 113.2 (2) |
N1B—C2B—C3B | 114.2 (2) | N1D—C2D—C1D | 111.43 (19) |
N1B—C2B—C1B | 111.8 (2) | C3D—C2D—C1D | 111.3 (2) |
C3B—C2B—C1B | 109.7 (2) | N1D—C2D—H2DA | 106.8 |
N1B—C2B—H2BA | 106.9 | C3D—C2D—H2DA | 106.8 |
C3B—C2B—H2BA | 106.9 | C1D—C2D—H2DA | 106.8 |
C1B—C2B—H2BA | 106.9 | C4D—C3D—C2D | 121.1 (2) |
C4B—C3B—C2B | 120.2 (2) | C4D—C3D—H3DA | 119.5 |
C4B—C3B—H3BA | 119.9 | C2D—C3D—H3DA | 119.5 |
C2B—C3B—H3BA | 119.9 | C3D—C4D—C5D | 121.4 (2) |
C3B—C4B—C5B | 120.9 (2) | C3D—C4D—H4DA | 119.3 |
C3B—C4B—H4BA | 119.5 | C5D—C4D—H4DA | 119.3 |
C5B—C4B—H4BA | 119.5 | C6D—C5D—C10D | 119.1 (2) |
C6B—C5B—C10B | 118.9 (3) | C6D—C5D—C4D | 121.4 (2) |
C6B—C5B—C4B | 121.6 (2) | C10D—C5D—C4D | 119.5 (2) |
C10B—C5B—C4B | 119.4 (2) | C7D—C6D—C5D | 120.8 (2) |
C7B—C6B—C5B | 120.6 (3) | C7D—C6D—H6DA | 119.6 |
C7B—C6B—H6BA | 119.7 | C5D—C6D—H6DA | 119.6 |
C5B—C6B—H6BA | 119.7 | C8D—C7D—C6D | 119.5 (3) |
C8B—C7B—C6B | 119.9 (3) | C8D—C7D—H7DA | 120.3 |
C8B—C7B—H7BA | 120.0 | C6D—C7D—H7DA | 120.3 |
C6B—C7B—H7BA | 120.0 | C7D—C8D—C9D | 120.7 (3) |
C7B—C8B—C9B | 120.1 (3) | C7D—C8D—H8DA | 119.6 |
C7B—C8B—H8BA | 120.0 | C9D—C8D—H8DA | 119.6 |
C9B—C8B—H8BA | 120.0 | C10D—C9D—C8D | 120.3 (2) |
C10B—C9B—C8B | 120.6 (3) | C10D—C9D—H9DA | 119.8 |
C10B—C9B—H9BA | 119.7 | C8D—C9D—H9DA | 119.8 |
C8B—C9B—H9BA | 119.7 | C9D—C10D—C5D | 119.5 (2) |
C9B—C10B—C5B | 119.9 (2) | C9D—C10D—C1D | 121.9 (2) |
C9B—C10B—C1B | 123.4 (2) | C5D—C10D—C1D | 118.5 (2) |
C5B—C10B—C1B | 116.7 (2) | N1D—C11D—C12D | 121.7 (2) |
N1B—C11B—C16B | 120.8 (2) | N1D—C11D—C16D | 120.5 (2) |
N1B—C11B—C12B | 122.4 (2) | C12D—C11D—C16D | 117.7 (2) |
C16B—C11B—C12B | 116.8 (2) | C13D—C12D—C11D | 120.7 (3) |
C13B—C12B—C11B | 120.9 (3) | C13D—C12D—H12D | 119.6 |
C13B—C12B—H12B | 119.5 | C11D—C12D—H12D | 119.6 |
C11B—C12B—H12B | 119.5 | C14D—C13D—C12D | 121.3 (3) |
C12B—C13B—C14B | 121.9 (3) | C14D—C13D—H13D | 119.4 |
C12B—C13B—H13B | 119.1 | C12D—C13D—H13D | 119.4 |
C14B—C13B—H13B | 119.1 | C13D—C14D—C15D | 118.8 (3) |
C15B—C14B—C13B | 117.9 (3) | C13D—C14D—H14D | 120.6 |
C15B—C14B—H14B | 121.1 | C15D—C14D—H14D | 120.6 |
C13B—C14B—H14B | 121.1 | C14D—C15D—C16D | 121.0 (3) |
C14B—C15B—C16B | 121.7 (3) | C14D—C15D—H15D | 119.5 |
C14B—C15B—H15B | 119.2 | C16D—C15D—H15D | 119.5 |
C16B—C15B—H15B | 119.2 | C15D—C16D—C11D | 120.4 (3) |
C15B—C16B—C11B | 120.9 (3) | C15D—C16D—H16D | 119.8 |
C15B—C16B—H16B | 119.6 | C11D—C16D—H16D | 119.8 |
C11B—C16B—H16B | 119.6 | N1D—C17D—H17J | 109.5 |
N1B—C17B—H17D | 109.5 | N1D—C17D—H17K | 109.5 |
N1B—C17B—H17E | 109.5 | H17J—C17D—H17K | 109.5 |
H17D—C17B—H17E | 109.5 | N1D—C17D—H17L | 109.5 |
N1B—C17B—H17F | 109.5 | H17J—C17D—H17L | 109.5 |
H17D—C17B—H17F | 109.5 | H17K—C17D—H17L | 109.5 |
H17E—C17B—H17F | 109.5 | H1W—O1W—H2W | 113 (4) |
C1C—O1C—H1OC | 109.5 | | |
| | | |
C11A—N1A—C2A—C3A | −85.5 (3) | C11C—N1C—C2C—C3C | −88.2 (3) |
C17A—N1A—C2A—C3A | 59.5 (3) | C17C—N1C—C2C—C3C | 56.6 (3) |
C11A—N1A—C2A—C1A | 145.7 (2) | C11C—N1C—C2C—C1C | 145.5 (2) |
C17A—N1A—C2A—C1A | −69.3 (3) | C17C—N1C—C2C—C1C | −69.7 (3) |
O1A—C1A—C2A—N1A | −61.3 (3) | O1C—C1C—C2C—N1C | −61.4 (3) |
C10A—C1A—C2A—N1A | 178.4 (2) | C10C—C1C—C2C—N1C | 177.63 (19) |
O1A—C1A—C2A—C3A | 168.5 (2) | O1C—C1C—C2C—C3C | 171.3 (2) |
C10A—C1A—C2A—C3A | 48.2 (3) | C10C—C1C—C2C—C3C | 50.3 (3) |
N1A—C2A—C3A—C4A | −163.8 (2) | N1C—C2C—C3C—C4C | −162.1 (2) |
C1A—C2A—C3A—C4A | −34.0 (3) | C1C—C2C—C3C—C4C | −35.3 (3) |
C2A—C3A—C4A—C5A | 0.0 (4) | C2C—C3C—C4C—C5C | 1.2 (4) |
C3A—C4A—C5A—C6A | −163.2 (3) | C3C—C4C—C5C—C6C | −162.1 (3) |
C3A—C4A—C5A—C10A | 17.9 (4) | C3C—C4C—C5C—C10C | 16.1 (4) |
C10A—C5A—C6A—C7A | −0.9 (4) | C10C—C5C—C6C—C7C | 0.1 (4) |
C4A—C5A—C6A—C7A | −179.9 (3) | C4C—C5C—C6C—C7C | 178.3 (3) |
C5A—C6A—C7A—C8A | 1.7 (4) | C5C—C6C—C7C—C8C | 0.8 (5) |
C6A—C7A—C8A—C9A | −0.8 (5) | C6C—C7C—C8C—C9C | −0.4 (5) |
C7A—C8A—C9A—C10A | −0.8 (5) | C7C—C8C—C9C—C10C | −0.8 (4) |
C8A—C9A—C10A—C5A | 1.5 (4) | C8C—C9C—C10C—C5C | 1.7 (4) |
C8A—C9A—C10A—C1A | 179.1 (3) | C8C—C9C—C10C—C1C | 178.7 (3) |
C6A—C5A—C10A—C9A | −0.6 (4) | C6C—C5C—C10C—C9C | −1.4 (4) |
C4A—C5A—C10A—C9A | 178.4 (2) | C4C—C5C—C10C—C9C | −179.6 (2) |
C6A—C5A—C10A—C1A | −178.3 (2) | C6C—C5C—C10C—C1C | −178.4 (2) |
C4A—C5A—C10A—C1A | 0.7 (3) | C4C—C5C—C10C—C1C | 3.3 (4) |
O1A—C1A—C10A—C9A | 27.5 (3) | O1C—C1C—C10C—C9C | 24.9 (3) |
C2A—C1A—C10A—C9A | 148.9 (3) | C2C—C1C—C10C—C9C | 146.9 (2) |
O1A—C1A—C10A—C5A | −154.8 (2) | O1C—C1C—C10C—C5C | −158.1 (2) |
C2A—C1A—C10A—C5A | −33.5 (3) | C2C—C1C—C10C—C5C | −36.1 (3) |
C17A—N1A—C11A—C16A | 3.6 (4) | C17C—N1C—C11C—C16C | 14.4 (3) |
C2A—N1A—C11A—C16A | 148.0 (2) | C2C—N1C—C11C—C16C | 158.4 (2) |
C17A—N1A—C11A—C12A | −178.1 (3) | C17C—N1C—C11C—C12C | −168.7 (2) |
C2A—N1A—C11A—C12A | −33.7 (4) | C2C—N1C—C11C—C12C | −24.7 (3) |
C16A—C11A—C12A—C13A | −3.9 (4) | C16C—C11C—C12C—C13C | 1.1 (4) |
N1A—C11A—C12A—C13A | 177.7 (3) | N1C—C11C—C12C—C13C | −175.9 (2) |
C11A—C12A—C13A—C14A | 1.9 (5) | C11C—C12C—C13C—C14C | 0.1 (4) |
C12A—C13A—C14A—C15A | 1.4 (5) | C12C—C13C—C14C—C15C | −0.6 (4) |
C13A—C14A—C15A—C16A | −2.5 (5) | C13C—C14C—C15C—C16C | −0.2 (4) |
C14A—C15A—C16A—C11A | 0.4 (5) | C14C—C15C—C16C—C11C | 1.5 (4) |
C12A—C11A—C16A—C15A | 2.8 (4) | C12C—C11C—C16C—C15C | −1.9 (4) |
N1A—C11A—C16A—C15A | −178.8 (3) | N1C—C11C—C16C—C15C | 175.2 (2) |
C11B—N1B—C2B—C3B | −106.1 (3) | C11D—N1D—C2D—C3D | −111.5 (2) |
C17B—N1B—C2B—C3B | 54.4 (3) | C17D—N1D—C2D—C3D | 47.5 (3) |
C11B—N1B—C2B—C1B | 128.6 (2) | C11D—N1D—C2D—C1D | 122.1 (2) |
C17B—N1B—C2B—C1B | −70.9 (3) | C17D—N1D—C2D—C1D | −78.9 (3) |
O1B—C1B—C2B—N1B | −56.5 (3) | O1D—C1D—C2D—N1D | −64.3 (2) |
C10B—C1B—C2B—N1B | −178.0 (2) | C10D—C1D—C2D—N1D | 173.72 (19) |
O1B—C1B—C2B—C3B | 175.69 (19) | O1D—C1D—C2D—C3D | 168.29 (19) |
C10B—C1B—C2B—C3B | 54.2 (3) | C10D—C1D—C2D—C3D | 46.3 (3) |
N1B—C2B—C3B—C4B | −162.3 (2) | N1D—C2D—C3D—C4D | −158.7 (2) |
C1B—C2B—C3B—C4B | −36.0 (3) | C1D—C2D—C3D—C4D | −32.3 (3) |
C2B—C3B—C4B—C5B | −0.2 (4) | C2D—C3D—C4D—C5D | 2.0 (4) |
C3B—C4B—C5B—C6B | −159.3 (3) | C3D—C4D—C5D—C6D | −164.4 (3) |
C3B—C4B—C5B—C10B | 17.1 (4) | C3D—C4D—C5D—C10D | 13.4 (4) |
C10B—C5B—C6B—C7B | −1.1 (4) | C10D—C5D—C6D—C7D | 0.2 (4) |
C4B—C5B—C6B—C7B | 175.4 (2) | C4D—C5D—C6D—C7D | 178.0 (2) |
C5B—C6B—C7B—C8B | 0.4 (4) | C5D—C6D—C7D—C8D | 0.2 (4) |
C6B—C7B—C8B—C9B | 0.6 (4) | C6D—C7D—C8D—C9D | −0.3 (4) |
C7B—C8B—C9B—C10B | −0.9 (4) | C7D—C8D—C9D—C10D | 0.0 (4) |
C8B—C9B—C10B—C5B | 0.2 (4) | C8D—C9D—C10D—C5D | 0.4 (4) |
C8B—C9B—C10B—C1B | 179.0 (2) | C8D—C9D—C10D—C1D | 177.5 (2) |
C6B—C5B—C10B—C9B | 0.8 (4) | C6D—C5D—C10D—C9D | −0.5 (3) |
C4B—C5B—C10B—C9B | −175.7 (2) | C4D—C5D—C10D—C9D | −178.4 (2) |
C6B—C5B—C10B—C1B | −178.1 (2) | C6D—C5D—C10D—C1D | −177.7 (2) |
C4B—C5B—C10B—C1B | 5.3 (3) | C4D—C5D—C10D—C1D | 4.4 (3) |
O1B—C1B—C10B—C9B | 18.0 (3) | O1D—C1D—C10D—C9D | 26.4 (3) |
C2B—C1B—C10B—C9B | 140.5 (2) | C2D—C1D—C10D—C9D | 148.7 (2) |
O1B—C1B—C10B—C5B | −163.1 (2) | O1D—C1D—C10D—C5D | −156.4 (2) |
C2B—C1B—C10B—C5B | −40.6 (3) | C2D—C1D—C10D—C5D | −34.1 (3) |
C17B—N1B—C11B—C16B | 5.3 (4) | C17D—N1D—C11D—C12D | 167.7 (2) |
C2B—N1B—C11B—C16B | 165.2 (2) | C2D—N1D—C11D—C12D | −34.0 (3) |
C17B—N1B—C11B—C12B | −176.2 (3) | C17D—N1D—C11D—C16D | −9.9 (4) |
C2B—N1B—C11B—C12B | −16.2 (4) | C2D—N1D—C11D—C16D | 148.5 (2) |
N1B—C11B—C12B—C13B | −179.2 (3) | N1D—C11D—C12D—C13D | −177.1 (2) |
C16B—C11B—C12B—C13B | −0.6 (4) | C16D—C11D—C12D—C13D | 0.5 (4) |
C11B—C12B—C13B—C14B | 0.1 (5) | C11D—C12D—C13D—C14D | −0.2 (4) |
C12B—C13B—C14B—C15B | 0.0 (5) | C12D—C13D—C14D—C15D | −0.6 (4) |
C13B—C14B—C15B—C16B | 0.6 (5) | C13D—C14D—C15D—C16D | 0.9 (4) |
C14B—C15B—C16B—C11B | −1.1 (5) | C14D—C15D—C16D—C11D | −0.6 (4) |
N1B—C11B—C16B—C15B | 179.8 (3) | N1D—C11D—C16D—C15D | 177.5 (2) |
C12B—C11B—C16B—C15B | 1.1 (4) | C12D—C11D—C16D—C15D | −0.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1OB···O1C | 0.84 | 2.08 | 2.881 (3) | 160 |
O1C—H1OC···O1D | 0.84 | 2.35 | 3.150 (3) | 160 |
O1D—H1OD···O1A | 0.84 | 2.04 | 2.847 (3) | 161 |
O1A—H1OA···O1Wi | 0.84 | 1.89 | 2.716 (3) | 169 |
O1W—H1W···O1B | 0.84 | 1.95 | 2.777 (3) | 167 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | 4C17H17NO·H2O |
Mr | 1023.28 |
Crystal system, space group | Trigonal, P31 |
Temperature (K) | 150 |
a, c (Å) | 12.3595 (1), 31.1411 (4) |
V (Å3) | 4119.71 (7) |
Z | 3 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.24 × 0.20 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 49468, 5415, 4878 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.090, 1.03 |
No. of reflections | 5415 |
No. of parameters | 708 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.22 |
Selected torsion angles (º) topC17A—N1A—C2A—C1A | −69.3 (3) | C17C—N1C—C2C—C1C | −69.7 (3) |
C17A—N1A—C11A—C16A | 3.6 (4) | C17C—N1C—C11C—C16C | 14.4 (3) |
C17B—N1B—C2B—C1B | −70.9 (3) | C17D—N1D—C2D—C1D | −78.9 (3) |
C17B—N1B—C11B—C16B | 5.3 (4) | C17D—N1D—C11D—C16D | −9.9 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1OB···O1C | 0.84 | 2.08 | 2.881 (3) | 160 |
O1C—H1OC···O1D | 0.84 | 2.35 | 3.150 (3) | 160 |
O1D—H1OD···O1A | 0.84 | 2.04 | 2.847 (3) | 161 |
O1A—H1OA···O1Wi | 0.84 | 1.89 | 2.716 (3) | 169 |
O1W—H1W···O1B | 0.84 | 1.95 | 2.777 (3) | 167 |
Symmetry code: (i) x+1, y, z. |
Recently, we reported a new rhodium-catalyzed ring-opening reaction of 1,4-dihydro-1,4-epoxynaphthalene with a wide range of nucleophiles (Lautens et al., 2000). The 1,2-regiochemistry and the trans relative stereochemistry of the title compound, (I), were established by our X-ray diffraction analysis when N-methylaniline is used as the nucleophile.
In (I), the four independent molecules (Figs. 1–4) and the water molecule are linked into a contiguous row through O—H···O hydrogen bonds (see Table 2 and Fig. 5). This hydrogen-bonded unit is, in turn, linked into extended O—H···O hydrogen-bonded chains through unit-cell translations in the a direction. The binary level graph set for this hydrogen-bonding motif is C55(10) (Bernstein et al.,1995). Only one of the H-atom donors from the water molecule is invloved in the above hydrogen-bonding motif. The other water H atom is involved in a weak O(water)—H···π(arene) bond [O1W···Cg = 3.384 (3) Å, H2W···Cg = 2.64 (4) Å and O1W—H2W···Cg = 148 (3)°, where Cg is the center of gravity of the phenyl ring containing atoms C5A/C6A/C7A/C8A/C9A/C10A]. The values for the O(water)—H ···π(arene) bond in (I) compare well with the mean values cited for other O—H..π(arene) bonds (Desiraju & Steiner, 1999).
The bond lengths and angles in the four molecules of (I) (A, B, C and D) are the same within experimental error, although there appears to be some differences with respect to the degree of rotation about the C11—N1 and N1—C2 bonds (see Table 1 for relevant torsion angles). In the dihydronaphthalene group, an analysis (Cremer & Pople, 1975) of the puckering in the six-membered ring (C1/C2/C3/C4/C5/C10) gives QT = 0.440 (3), 0.487 (3), 0.453 (3) and 0.411 (3) Å for molecules A, B, C and D, respectively. In all molecules, the conformation analysis of that ring (Duax et al., 1976) shows that the conformation is a half-chair, with a local pseudo-twofold axis running through the midpoints of the C1—C2 and C4—C5 bonds.