organic compounds
3,5,7-Tripropyl-1-azaadamantane-4,6,10-triol
aLaboratoire de Chimie, UMR CNRS 5182, Ecole Normale Supérieure de Lyon, 46 Allée d'Italie, 69364 Lyon, France, and bCentre de Diffractométrie Henri Longchambon, Université Claude Bernard Lyon1, 43 boulevard du 11 novembre 1918, 69622 Villeurbanne Cedex, France
*Correspondence e-mail: erwann.jeanneau@univ-lyon1.fr
The title compound, C18H33NO3, was prepared according to a highly diastereoselective hydrogenation procedure from 3,5,7-triallyl-1-azaadamantane-4,6,10-trione. The of the title compound contains two crystallographically independent molecules (Z′ = 2), which are linked by intermolecular hydrogen bonding into chains. In contrast to the azaadamantanones, the azaadamantanetriol core of the title compound does not show any particular C—C bond elongation.
Related literature
For related literature on the consequences of through-bond donor–acceptor interactions in β-aminoketones azaadamantones, see: Lampkins et al. (2008). For details on molecular receptors based on a polyfunctionalized rigid platform, see: Guarise et al. (2006); Haberhauer et al. (2005); Li et al. (2005). For information about molecules displaying multiple formula units per crystallographic see: Steiner (2000). For bond lengths in similar compounds, see: Lampkins et al. (2008); Allen et al. (1987). Details on the synthesis can be found in: Risch (1985); Li et al. (2005). For details of data collection and procedures, see: Görbitz (1999); Guarise et al. (2006); Prince (1982); Watkin (1994).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 2001).; cell DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg & Putz, 1996); software used to prepare material for publication: CRYSTALS.
Supporting information
10.1107/S1600536808006284/nc2092sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808006284/nc2092Isup2.hkl
The title compound was prepared according to a hydrogenation procedure adapted from Risch (1985). A 100-ml reactor vessel was charged with 80 mg of 3,5,7-triallyl-1-aza-adamantane-4,6,10-trione (0.267 mmol) (Li et al., 2005), 88 mg of platinum oxide (0.388 mmol) and 20 ml of a 1:1 THF/0.1 N HCl mixture. The reaction mixture was hydrogenated (10 bar H2) for 50 h at room temperature. After filtration over Celite, the aqueous solution was concentrated under reduced pressure (200 mbar) basified with potassium carbonate and extracted with four 80-ml portions of ethyl acetate. The combined organic phases were then dried over Na2SO4 and concentrated in vacuo. Flash
purification (petroleum ether/ethyl acetate 1:1 then neat ethyl acetate) afforded the title compound as a cristalline white powder (54 mg, 65%). X-ray quality single crystals were obtained by slow evaporation from a cyclohexane/ethyl acetate solution.Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). All non hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were all located in a difference map and initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.954–1.014 and O—H = 0.794–0.836 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom). In the final
the H-atoms were refined using a riding model.Data collection: COLLECT (Nonius, 2001).; cell
DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg & Putz, 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).Fig. 1. Molecule A of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms have been omitted fo clarity. | |
Fig. 2. Molecule B of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms have been omitted fo clarity. |
C18H33NO3 | F(000) = 1376 |
Mr = 311.45 | Dx = 1.162 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 8626 reflections |
a = 13.1922 (2) Å | θ = 0.7–27.9° |
b = 22.6174 (5) Å | µ = 0.08 mm−1 |
c = 13.1144 (3) Å | T = 150 K |
β = 114.447 (1)° | Block, colorless |
V = 3562.17 (13) Å3 | 0.43 × 0.35 × 0.14 mm |
Z = 8 |
Nonius KappaCCD diffractometer | Rint = 0.027 |
Graphite monochromator | θmax = 27.9°, θmin = 1.8° |
ϕ & ω scans | h = −16→17 |
16642 measured reflections | k = −29→29 |
8498 independent reflections | l = −17→17 |
5272 reflections with I > 2σ(I) |
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.054 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.361 0.287 0.915E-01 |
S = 1.06 | (Δ/σ)max = 0.000263 |
5272 reflections | Δρmax = 0.29 e Å−3 |
397 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
C18H33NO3 | V = 3562.17 (13) Å3 |
Mr = 311.45 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1922 (2) Å | µ = 0.08 mm−1 |
b = 22.6174 (5) Å | T = 150 K |
c = 13.1144 (3) Å | 0.43 × 0.35 × 0.14 mm |
β = 114.447 (1)° |
Nonius KappaCCD diffractometer | 5272 reflections with I > 2σ(I) |
16642 measured reflections | Rint = 0.027 |
8498 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.29 e Å−3 |
5272 reflections | Δρmin = −0.18 e Å−3 |
397 parameters |
x | y | z | Uiso*/Ueq | ||
O4 | 0.22669 (10) | 0.25151 (5) | 0.14425 (9) | 0.0370 | |
C22 | 0.31510 (13) | 0.23591 (7) | 0.24925 (13) | 0.0319 | |
C21 | 0.32122 (13) | 0.16842 (7) | 0.27185 (13) | 0.0317 | |
C28 | 0.22217 (13) | 0.14597 (8) | 0.29517 (13) | 0.0321 | |
O6 | 0.11955 (9) | 0.14471 (6) | 0.19701 (9) | 0.0394 | |
C25 | 0.21442 (12) | 0.18139 (7) | 0.39228 (13) | 0.0307 | |
C24 | 0.20674 (12) | 0.24822 (7) | 0.36626 (13) | 0.0307 | |
C23 | 0.30828 (13) | 0.27030 (7) | 0.34760 (13) | 0.0318 | |
C32 | 0.30115 (14) | 0.33789 (8) | 0.32981 (15) | 0.0363 | |
C33 | 0.40054 (15) | 0.36720 (8) | 0.31923 (16) | 0.0427 | |
C34 | 0.38186 (18) | 0.43335 (9) | 0.29532 (17) | 0.0490 | |
C27 | 0.41327 (13) | 0.25457 (7) | 0.45347 (14) | 0.0335 | |
N2 | 0.42274 (11) | 0.19088 (6) | 0.47731 (11) | 0.0325 | |
C26 | 0.32503 (13) | 0.17096 (8) | 0.49585 (13) | 0.0323 | |
C20 | 0.42662 (13) | 0.15834 (8) | 0.38098 (13) | 0.0332 | |
O5 | 0.10637 (9) | 0.26078 (5) | 0.26700 (9) | 0.0358 | |
C35 | 0.11432 (13) | 0.16295 (8) | 0.41669 (14) | 0.0348 | |
C36 | 0.11823 (16) | 0.10271 (9) | 0.47005 (18) | 0.0468 | |
C37 | 0.01314 (19) | 0.09196 (11) | 0.4888 (2) | 0.0652 | |
C29 | 0.32990 (14) | 0.13606 (8) | 0.17273 (14) | 0.0360 | |
C30 | 0.33494 (17) | 0.06849 (8) | 0.17741 (15) | 0.0426 | |
C31 | 0.33958 (17) | 0.04267 (9) | 0.07231 (16) | 0.0464 | |
O2 | 0.67551 (10) | 0.29792 (6) | 0.42136 (11) | 0.0413 | |
C6 | 0.77461 (13) | 0.29360 (8) | 0.40309 (14) | 0.0353 | |
C7 | 0.75659 (13) | 0.26000 (8) | 0.29401 (14) | 0.0338 | |
C8 | 0.87254 (14) | 0.25041 (8) | 0.29625 (15) | 0.0380 | |
N1 | 0.93330 (11) | 0.30585 (7) | 0.30284 (12) | 0.0385 | |
C2 | 0.86849 (14) | 0.34194 (9) | 0.20364 (14) | 0.0380 | |
C3 | 0.75199 (13) | 0.35754 (8) | 0.19632 (13) | 0.0333 | |
C10 | 0.69017 (12) | 0.29876 (8) | 0.19190 (13) | 0.0320 | |
O3 | 0.58136 (9) | 0.30951 (5) | 0.18883 (9) | 0.0341 | |
C4 | 0.76841 (13) | 0.39174 (8) | 0.30365 (13) | 0.0350 | |
C5 | 0.83343 (13) | 0.35359 (8) | 0.40852 (14) | 0.0351 | |
C9 | 0.94652 (14) | 0.33854 (9) | 0.40532 (14) | 0.0392 | |
C14 | 0.85052 (15) | 0.38593 (8) | 0.51758 (14) | 0.0402 | |
C15 | 0.91418 (17) | 0.44422 (9) | 0.54001 (16) | 0.0468 | |
C16 | 0.9286 (2) | 0.47099 (10) | 0.65167 (17) | 0.0577 | |
O1 | 0.66640 (10) | 0.41465 (6) | 0.30104 (10) | 0.0421 | |
C11 | 0.68602 (14) | 0.39337 (8) | 0.08912 (14) | 0.0377 | |
C12 | 0.72891 (18) | 0.45457 (9) | 0.08051 (17) | 0.0520 | |
C13 | 0.6514 (2) | 0.48575 (10) | −0.02511 (18) | 0.0578 | |
C17 | 0.70163 (15) | 0.19948 (8) | 0.29070 (15) | 0.0399 | |
C18 | 0.6838 (2) | 0.16093 (9) | 0.19042 (19) | 0.0578 | |
C19 | 0.6477 (2) | 0.09893 (10) | 0.1998 (2) | 0.0639 | |
H221 | 0.3844 | 0.2468 | 0.2435 | 0.0364* | |
H281 | 0.2387 | 0.1039 | 0.3201 | 0.0372* | |
H241 | 0.2047 | 0.2695 | 0.4312 | 0.0362* | |
H321 | 0.2918 | 0.3557 | 0.3926 | 0.0433* | |
H322 | 0.2344 | 0.3461 | 0.2617 | 0.0433* | |
H331 | 0.4665 | 0.3621 | 0.3906 | 0.0517* | |
H332 | 0.4140 | 0.3482 | 0.2579 | 0.0522* | |
H341 | 0.4453 | 0.4515 | 0.2884 | 0.0734* | |
H342 | 0.3710 | 0.4531 | 0.3553 | 0.0734* | |
H343 | 0.3152 | 0.4400 | 0.2268 | 0.0738* | |
H271 | 0.4115 | 0.2754 | 0.5181 | 0.0400* | |
H272 | 0.4803 | 0.2669 | 0.4441 | 0.0397* | |
H261 | 0.3231 | 0.1927 | 0.5587 | 0.0376* | |
H262 | 0.3335 | 0.1285 | 0.5132 | 0.0369* | |
H201 | 0.4923 | 0.1716 | 0.3704 | 0.0379* | |
H202 | 0.4354 | 0.1162 | 0.4003 | 0.0387* | |
H351 | 0.1073 | 0.1926 | 0.4673 | 0.0420* | |
H352 | 0.0468 | 0.1652 | 0.3451 | 0.0413* | |
H361 | 0.1826 | 0.1005 | 0.5424 | 0.0572* | |
H362 | 0.1255 | 0.0714 | 0.4211 | 0.0579* | |
H372 | 0.0181 | 0.0545 | 0.5240 | 0.1066* | |
H373 | 0.0058 | 0.1234 | 0.5365 | 0.1065* | |
H371 | −0.0529 | 0.0913 | 0.4176 | 0.1066* | |
H292 | 0.3977 | 0.1499 | 0.1666 | 0.0441* | |
H291 | 0.2660 | 0.1473 | 0.1059 | 0.0432* | |
H302 | 0.3993 | 0.0553 | 0.2435 | 0.0525* | |
H301 | 0.2675 | 0.0528 | 0.1838 | 0.0534* | |
H312 | 0.3437 | −0.0001 | 0.0775 | 0.0710* | |
H311 | 0.4058 | 0.0579 | 0.0642 | 0.0701* | |
H313 | 0.2727 | 0.0538 | 0.0072 | 0.0718* | |
H81 | 0.9151 | 0.2263 | 0.3611 | 0.0457* | |
H82 | 0.8659 | 0.2291 | 0.2287 | 0.0451* | |
H101 | 0.6800 | 0.2775 | 0.1226 | 0.0385* | |
H41 | 0.8178 | 0.4270 | 0.3091 | 0.0411* | |
H91 | 0.9852 | 0.3762 | 0.4079 | 0.0453* | |
H92 | 0.9911 | 0.3150 | 0.4707 | 0.0451* | |
H141 | 0.8903 | 0.3587 | 0.5797 | 0.0480* | |
H142 | 0.7783 | 0.3931 | 0.5183 | 0.0461* | |
H151 | 0.9877 | 0.4377 | 0.5396 | 0.0542* | |
H152 | 0.8730 | 0.4720 | 0.4804 | 0.0538* | |
H161 | 0.9692 | 0.5090 | 0.6648 | 0.0816* | |
H163 | 0.9716 | 0.4448 | 0.7131 | 0.0814* | |
H162 | 0.8570 | 0.4791 | 0.6549 | 0.0813* | |
H112 | 0.6828 | 0.3697 | 0.0256 | 0.0445* | |
H111 | 0.6100 | 0.3982 | 0.0830 | 0.0418* | |
H122 | 0.8028 | 0.4512 | 0.0804 | 0.0611* | |
H121 | 0.7358 | 0.4786 | 0.1446 | 0.0606* | |
H132 | 0.6794 | 0.5245 | −0.0329 | 0.0821* | |
H131 | 0.6403 | 0.4627 | −0.0907 | 0.0830* | |
H133 | 0.5790 | 0.4914 | −0.0244 | 0.0836* | |
H171 | 0.7490 | 0.1778 | 0.3584 | 0.0495* | |
H172 | 0.6303 | 0.2058 | 0.2953 | 0.0493* | |
H181 | 0.7507 | 0.1601 | 0.1784 | 0.0724* | |
H182 | 0.6265 | 0.1791 | 0.1236 | 0.0733* | |
H192 | 0.6309 | 0.0768 | 0.1305 | 0.0976* | |
H193 | 0.7068 | 0.0790 | 0.2604 | 0.0985* | |
H191 | 0.5823 | 0.0993 | 0.2172 | 0.0980* | |
H61 | 0.8258 | 0.2699 | 0.4657 | 0.0408* | |
H3 | 0.5379 | 0.3125 | 0.1209 | 0.0493* | |
H2 | 0.6248 | 0.3068 | 0.3608 | 0.0653* | |
H4 | 0.1729 | 0.2612 | 0.1586 | 0.0565* | |
H5 | 0.0605 | 0.2783 | 0.2841 | 0.0541* | |
H1 | 0.6209 | 0.3901 | 0.2705 | 0.0617* | |
H6 | 0.0936 | 0.1786 | 0.1939 | 0.0573* | |
H21 | 0.9078 | 0.3782 | 0.2069 | 0.0497* | |
H22 | 0.8620 | 0.3215 | 0.1358 | 0.0487* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0343 (6) | 0.0458 (7) | 0.0311 (6) | 0.0050 (5) | 0.0137 (5) | 0.0050 (5) |
C22 | 0.0273 (7) | 0.0388 (9) | 0.0293 (8) | 0.0020 (6) | 0.0116 (6) | 0.0026 (6) |
C21 | 0.0291 (8) | 0.0384 (8) | 0.0284 (7) | 0.0031 (6) | 0.0126 (6) | 0.0005 (6) |
C28 | 0.0279 (7) | 0.0374 (8) | 0.0287 (7) | −0.0001 (6) | 0.0093 (6) | 0.0001 (6) |
O6 | 0.0324 (6) | 0.0493 (7) | 0.0323 (6) | −0.0034 (5) | 0.0091 (5) | −0.0039 (5) |
C25 | 0.0259 (7) | 0.0370 (8) | 0.0297 (8) | 0.0015 (6) | 0.0119 (6) | 0.0009 (6) |
C24 | 0.0263 (7) | 0.0367 (8) | 0.0288 (7) | 0.0024 (6) | 0.0113 (6) | 0.0015 (6) |
C23 | 0.0285 (7) | 0.0350 (8) | 0.0323 (8) | 0.0013 (6) | 0.0128 (6) | 0.0010 (6) |
C32 | 0.0349 (8) | 0.0369 (9) | 0.0381 (9) | 0.0024 (7) | 0.0163 (7) | 0.0005 (7) |
C33 | 0.0433 (10) | 0.0418 (10) | 0.0456 (10) | −0.0037 (8) | 0.0210 (8) | −0.0041 (8) |
C34 | 0.0589 (12) | 0.0426 (10) | 0.0478 (10) | −0.0065 (9) | 0.0245 (9) | 0.0020 (8) |
C27 | 0.0267 (7) | 0.0394 (9) | 0.0326 (8) | 0.0008 (6) | 0.0105 (6) | −0.0015 (7) |
N2 | 0.0265 (6) | 0.0394 (7) | 0.0308 (7) | 0.0020 (5) | 0.0111 (5) | 0.0001 (6) |
C26 | 0.0282 (7) | 0.0392 (9) | 0.0288 (8) | 0.0032 (6) | 0.0110 (6) | 0.0016 (6) |
C20 | 0.0278 (8) | 0.0410 (9) | 0.0314 (8) | 0.0048 (6) | 0.0130 (6) | 0.0011 (6) |
O5 | 0.0264 (5) | 0.0481 (7) | 0.0328 (6) | 0.0075 (5) | 0.0121 (5) | 0.0040 (5) |
C35 | 0.0289 (8) | 0.0404 (9) | 0.0352 (8) | 0.0007 (7) | 0.0135 (7) | 0.0011 (7) |
C36 | 0.0419 (10) | 0.0494 (11) | 0.0528 (11) | 0.0029 (8) | 0.0233 (9) | 0.0110 (9) |
C37 | 0.0587 (13) | 0.0608 (14) | 0.0930 (18) | −0.0020 (11) | 0.0483 (13) | 0.0190 (13) |
C29 | 0.0375 (9) | 0.0402 (9) | 0.0331 (8) | 0.0017 (7) | 0.0175 (7) | −0.0010 (7) |
C30 | 0.0536 (11) | 0.0412 (10) | 0.0369 (9) | 0.0001 (8) | 0.0228 (8) | −0.0020 (7) |
C31 | 0.0568 (11) | 0.0452 (10) | 0.0413 (10) | −0.0021 (9) | 0.0245 (9) | −0.0061 (8) |
O2 | 0.0349 (6) | 0.0527 (8) | 0.0416 (6) | 0.0001 (5) | 0.0211 (5) | 0.0007 (6) |
C6 | 0.0289 (8) | 0.0454 (9) | 0.0318 (8) | 0.0045 (7) | 0.0127 (6) | 0.0035 (7) |
C7 | 0.0295 (8) | 0.0390 (9) | 0.0341 (8) | 0.0035 (7) | 0.0145 (6) | 0.0015 (7) |
C8 | 0.0308 (8) | 0.0448 (10) | 0.0388 (9) | 0.0054 (7) | 0.0148 (7) | 0.0018 (7) |
N1 | 0.0295 (7) | 0.0484 (9) | 0.0376 (7) | 0.0019 (6) | 0.0139 (6) | −0.0005 (6) |
C2 | 0.0308 (8) | 0.0489 (10) | 0.0359 (9) | −0.0027 (7) | 0.0156 (7) | 0.0004 (7) |
C3 | 0.0295 (8) | 0.0387 (8) | 0.0323 (8) | −0.0026 (7) | 0.0133 (6) | 0.0001 (7) |
C10 | 0.0252 (7) | 0.0399 (9) | 0.0320 (8) | 0.0005 (6) | 0.0129 (6) | −0.0005 (6) |
O3 | 0.0246 (5) | 0.0460 (7) | 0.0304 (5) | 0.0011 (5) | 0.0103 (4) | 0.0000 (5) |
C4 | 0.0285 (8) | 0.0433 (9) | 0.0323 (8) | −0.0009 (7) | 0.0118 (6) | −0.0004 (7) |
C5 | 0.0282 (8) | 0.0445 (9) | 0.0314 (8) | 0.0007 (7) | 0.0110 (6) | 0.0005 (7) |
C9 | 0.0291 (8) | 0.0518 (11) | 0.0344 (8) | 0.0001 (7) | 0.0108 (7) | 0.0000 (7) |
C14 | 0.0353 (9) | 0.0511 (11) | 0.0324 (8) | 0.0014 (8) | 0.0121 (7) | −0.0009 (7) |
C15 | 0.0441 (10) | 0.0503 (11) | 0.0395 (9) | −0.0010 (8) | 0.0108 (8) | −0.0031 (8) |
C16 | 0.0637 (13) | 0.0567 (13) | 0.0444 (11) | −0.0011 (10) | 0.0141 (10) | −0.0097 (9) |
O1 | 0.0347 (6) | 0.0481 (7) | 0.0407 (6) | 0.0053 (5) | 0.0127 (5) | −0.0058 (6) |
C11 | 0.0360 (9) | 0.0427 (9) | 0.0318 (8) | −0.0043 (7) | 0.0115 (7) | 0.0005 (7) |
C12 | 0.0532 (11) | 0.0482 (11) | 0.0472 (11) | −0.0104 (9) | 0.0133 (9) | 0.0067 (9) |
C13 | 0.0705 (14) | 0.0475 (12) | 0.0478 (11) | −0.0071 (10) | 0.0170 (10) | 0.0088 (9) |
C17 | 0.0400 (9) | 0.0391 (9) | 0.0432 (9) | 0.0016 (7) | 0.0200 (8) | 0.0034 (7) |
C18 | 0.0787 (15) | 0.0433 (11) | 0.0572 (13) | −0.0092 (10) | 0.0340 (12) | −0.0053 (9) |
C19 | 0.0616 (14) | 0.0473 (12) | 0.0867 (17) | −0.0052 (10) | 0.0344 (13) | −0.0071 (12) |
O4—C22 | 1.4323 (19) | O2—C6 | 1.427 (2) |
O4—H4 | 0.836 | O2—H2 | 0.824 |
C22—C21 | 1.551 (2) | C6—C7 | 1.549 (2) |
C22—C23 | 1.540 (2) | C6—C5 | 1.550 (2) |
C22—H221 | 0.979 | C6—H61 | 0.979 |
C21—C28 | 1.546 (2) | C7—C8 | 1.533 (2) |
C21—C20 | 1.545 (2) | C7—C10 | 1.536 (2) |
C21—C29 | 1.537 (2) | C7—C17 | 1.541 (2) |
C28—O6 | 1.4311 (19) | C8—N1 | 1.471 (2) |
C28—C25 | 1.543 (2) | C8—H81 | 0.970 |
C28—H281 | 1.000 | C8—H82 | 0.980 |
O6—H6 | 0.833 | N1—C2 | 1.473 (2) |
C25—C24 | 1.544 (2) | N1—C9 | 1.480 (2) |
C25—C26 | 1.546 (2) | C2—C3 | 1.541 (2) |
C25—C35 | 1.540 (2) | C2—H21 | 0.962 |
C24—C23 | 1.541 (2) | C2—H22 | 0.974 |
C24—O5 | 1.4498 (18) | C3—C10 | 1.548 (2) |
C24—H241 | 0.988 | C3—C4 | 1.541 (2) |
C23—C32 | 1.543 (2) | C3—C11 | 1.542 (2) |
C23—C27 | 1.543 (2) | C10—O3 | 1.4400 (19) |
C32—C33 | 1.526 (2) | C10—H101 | 0.987 |
C32—H321 | 0.969 | O3—H3 | 0.839 |
C32—H322 | 0.978 | C4—C5 | 1.548 (2) |
C33—C34 | 1.528 (3) | C4—O1 | 1.429 (2) |
C33—H331 | 0.986 | C4—H41 | 1.014 |
C33—H332 | 0.990 | C5—C9 | 1.548 (2) |
C34—H341 | 0.970 | C5—C14 | 1.538 (2) |
C34—H342 | 0.965 | C9—H91 | 0.986 |
C34—H343 | 0.974 | C9—H92 | 0.973 |
C27—N2 | 1.468 (2) | C14—C15 | 1.525 (3) |
C27—H271 | 0.978 | C14—H141 | 0.982 |
C27—H272 | 0.982 | C14—H142 | 0.970 |
N2—C26 | 1.477 (2) | C15—C16 | 1.522 (3) |
N2—C20 | 1.481 (2) | C15—H151 | 0.983 |
C26—H261 | 0.969 | C15—H152 | 0.975 |
C26—H262 | 0.982 | C16—H161 | 0.990 |
C20—H201 | 0.979 | C16—H163 | 0.972 |
C20—H202 | 0.981 | C16—H162 | 0.981 |
O5—H5 | 0.829 | O1—H1 | 0.794 |
C35—C36 | 1.523 (3) | C11—C12 | 1.517 (3) |
C35—H351 | 0.974 | C11—H112 | 0.976 |
C35—H352 | 0.992 | C11—H111 | 0.979 |
C36—C37 | 1.525 (3) | C12—C13 | 1.513 (3) |
C36—H361 | 0.978 | C12—H122 | 0.978 |
C36—H362 | 0.987 | C12—H121 | 0.973 |
C37—H372 | 0.954 | C13—H132 | 0.974 |
C37—H373 | 0.978 | C13—H131 | 0.964 |
C37—H371 | 0.979 | C13—H133 | 0.967 |
C29—C30 | 1.530 (3) | C17—C18 | 1.513 (3) |
C29—H292 | 0.981 | C17—H171 | 0.980 |
C29—H291 | 0.965 | C17—H172 | 0.977 |
C30—C31 | 1.521 (3) | C18—C19 | 1.502 (3) |
C30—H302 | 0.976 | C18—H181 | 0.960 |
C30—H301 | 0.992 | C18—H182 | 0.980 |
C31—H312 | 0.969 | C19—H192 | 0.980 |
C31—H311 | 0.986 | C19—H193 | 0.964 |
C31—H313 | 0.973 | C19—H191 | 0.979 |
C22—O4—H4 | 106.1 | C6—O2—H2 | 106.8 |
O4—C22—C21 | 112.55 (13) | O2—C6—C7 | 112.81 (14) |
O4—C22—C23 | 111.96 (13) | O2—C6—C5 | 114.11 (14) |
C21—C22—C23 | 110.71 (13) | C7—C6—C5 | 110.76 (13) |
O4—C22—H221 | 106.2 | O2—C6—H61 | 105.0 |
C21—C22—H221 | 106.7 | C7—C6—H61 | 107.1 |
C23—C22—H221 | 108.5 | C5—C6—H61 | 106.4 |
C22—C21—C28 | 112.32 (13) | C6—C7—C8 | 106.33 (14) |
C22—C21—C20 | 106.14 (13) | C6—C7—C10 | 109.84 (14) |
C28—C21—C20 | 106.18 (13) | C8—C7—C10 | 107.59 (13) |
C22—C21—C29 | 108.86 (13) | C6—C7—C17 | 110.63 (14) |
C28—C21—C29 | 112.08 (14) | C8—C7—C17 | 109.20 (14) |
C20—C21—C29 | 111.09 (13) | C10—C7—C17 | 112.98 (14) |
C21—C28—O6 | 113.01 (13) | C7—C8—N1 | 113.30 (14) |
C21—C28—C25 | 110.05 (13) | C7—C8—H81 | 107.9 |
O6—C28—C25 | 113.04 (13) | N1—C8—H81 | 108.9 |
C21—C28—H281 | 106.8 | C7—C8—H82 | 109.7 |
O6—C28—H281 | 105.8 | N1—C8—H82 | 108.4 |
C25—C28—H281 | 107.7 | H81—C8—H82 | 108.6 |
C28—O6—H6 | 104.0 | C8—N1—C2 | 108.51 (13) |
C28—C25—C24 | 110.28 (13) | C8—N1—C9 | 109.61 (14) |
C28—C25—C26 | 106.56 (12) | C2—N1—C9 | 109.42 (14) |
C24—C25—C26 | 107.18 (13) | N1—C2—C3 | 112.43 (14) |
C28—C25—C35 | 112.72 (13) | N1—C2—H21 | 109.2 |
C24—C25—C35 | 109.14 (13) | C3—C2—H21 | 108.2 |
C26—C25—C35 | 110.79 (13) | N1—C2—H22 | 110.1 |
C25—C24—C23 | 111.76 (13) | C3—C2—H22 | 110.1 |
C25—C24—O5 | 110.02 (13) | H21—C2—H22 | 106.6 |
C23—C24—O5 | 108.96 (12) | C2—C3—C10 | 107.58 (14) |
C25—C24—H241 | 108.0 | C2—C3—C4 | 107.37 (13) |
C23—C24—H241 | 108.3 | C10—C3—C4 | 109.76 (13) |
O5—C24—H241 | 109.7 | C2—C3—C11 | 110.44 (13) |
C22—C23—C24 | 108.97 (13) | C10—C3—C11 | 109.11 (13) |
C22—C23—C32 | 113.24 (14) | C4—C3—C11 | 112.46 (14) |
C24—C23—C32 | 110.03 (13) | C7—C10—C3 | 110.85 (13) |
C22—C23—C27 | 107.17 (13) | C7—C10—O3 | 108.86 (13) |
C24—C23—C27 | 107.33 (13) | C3—C10—O3 | 111.07 (13) |
C32—C23—C27 | 109.90 (13) | C7—C10—H101 | 109.6 |
C23—C32—C33 | 116.31 (14) | C3—C10—H101 | 108.8 |
C23—C32—H321 | 107.7 | O3—C10—H101 | 107.6 |
C33—C32—H321 | 108.2 | C10—O3—H3 | 106.2 |
C23—C32—H322 | 107.5 | C3—C4—C5 | 110.40 (14) |
C33—C32—H322 | 108.5 | C3—C4—O1 | 112.65 (13) |
H321—C32—H322 | 108.3 | C5—C4—O1 | 113.17 (14) |
C32—C33—C34 | 111.86 (16) | C3—C4—H41 | 107.6 |
C32—C33—H331 | 108.5 | C5—C4—H41 | 105.8 |
C34—C33—H331 | 108.3 | O1—C4—H41 | 106.8 |
C32—C33—H332 | 109.5 | C4—C5—C6 | 111.37 (13) |
C34—C33—H332 | 109.1 | C4—C5—C9 | 106.53 (14) |
H331—C33—H332 | 109.6 | C6—C5—C9 | 106.02 (14) |
C33—C34—H341 | 111.2 | C4—C5—C14 | 112.05 (15) |
C33—C34—H342 | 110.6 | C6—C5—C14 | 109.69 (14) |
H341—C34—H342 | 107.8 | C9—C5—C14 | 110.97 (14) |
C33—C34—H343 | 110.3 | C5—C9—N1 | 112.46 (14) |
H341—C34—H343 | 109.5 | C5—C9—H91 | 107.4 |
H342—C34—H343 | 107.3 | N1—C9—H91 | 109.1 |
C23—C27—N2 | 112.55 (13) | C5—C9—H92 | 109.6 |
C23—C27—H271 | 109.6 | N1—C9—H92 | 109.1 |
N2—C27—H271 | 108.5 | H91—C9—H92 | 109.1 |
C23—C27—H272 | 109.9 | C5—C14—C15 | 116.59 (15) |
N2—C27—H272 | 107.7 | C5—C14—H141 | 107.2 |
H271—C27—H272 | 108.5 | C15—C14—H141 | 108.6 |
C27—N2—C26 | 109.33 (12) | C5—C14—H142 | 108.8 |
C27—N2—C20 | 109.62 (13) | C15—C14—H142 | 108.6 |
C26—N2—C20 | 109.22 (13) | H141—C14—H142 | 106.6 |
C25—C26—N2 | 112.30 (13) | C14—C15—C16 | 111.66 (17) |
C25—C26—H261 | 108.8 | C14—C15—H151 | 109.6 |
N2—C26—H261 | 108.5 | C16—C15—H151 | 109.5 |
C25—C26—H262 | 109.2 | C14—C15—H152 | 108.9 |
N2—C26—H262 | 108.3 | C16—C15—H152 | 108.7 |
H261—C26—H262 | 109.8 | H151—C15—H152 | 108.4 |
C21—C20—N2 | 112.41 (13) | C15—C16—H161 | 110.9 |
C21—C20—H201 | 109.5 | C15—C16—H163 | 110.6 |
N2—C20—H201 | 108.2 | H161—C16—H163 | 107.3 |
C21—C20—H202 | 110.3 | C15—C16—H162 | 112.2 |
N2—C20—H202 | 107.7 | H161—C16—H162 | 106.9 |
H201—C20—H202 | 108.5 | H163—C16—H162 | 108.7 |
C24—O5—H5 | 110.4 | C4—O1—H1 | 105.5 |
C25—C35—C36 | 117.98 (14) | C3—C11—C12 | 117.40 (15) |
C25—C35—H351 | 106.7 | C3—C11—H112 | 107.4 |
C36—C35—H351 | 107.3 | C12—C11—H112 | 108.8 |
C25—C35—H352 | 107.5 | C3—C11—H111 | 107.8 |
C36—C35—H352 | 109.1 | C12—C11—H111 | 107.0 |
H351—C35—H352 | 108.0 | H112—C11—H111 | 108.1 |
C35—C36—C37 | 110.91 (17) | C11—C12—C13 | 111.20 (16) |
C35—C36—H361 | 109.9 | C11—C12—H122 | 109.4 |
C37—C36—H361 | 108.6 | C13—C12—H122 | 109.3 |
C35—C36—H362 | 109.7 | C11—C12—H121 | 110.5 |
C37—C36—H362 | 109.3 | C13—C12—H121 | 108.5 |
H361—C36—H362 | 108.4 | H122—C12—H121 | 107.9 |
C36—C37—H372 | 109.6 | C12—C13—H132 | 111.9 |
C36—C37—H373 | 109.0 | C12—C13—H131 | 111.1 |
H372—C37—H373 | 110.0 | H132—C13—H131 | 108.5 |
C36—C37—H371 | 111.0 | C12—C13—H133 | 110.4 |
H372—C37—H371 | 107.7 | H132—C13—H133 | 107.5 |
H373—C37—H371 | 109.6 | H131—C13—H133 | 107.2 |
C21—C29—C30 | 117.32 (14) | C7—C17—C18 | 116.01 (15) |
C21—C29—H292 | 107.9 | C7—C17—H171 | 107.6 |
C30—C29—H292 | 107.2 | C18—C17—H171 | 108.2 |
C21—C29—H291 | 107.4 | C7—C17—H172 | 108.8 |
C30—C29—H291 | 107.9 | C18—C17—H172 | 109.3 |
H292—C29—H291 | 108.9 | H171—C17—H172 | 106.7 |
C29—C30—C31 | 111.38 (15) | C17—C18—C19 | 114.05 (19) |
C29—C30—H302 | 110.4 | C17—C18—H181 | 109.4 |
C31—C30—H302 | 109.9 | C19—C18—H181 | 109.8 |
C29—C30—H301 | 109.5 | C17—C18—H182 | 108.6 |
C31—C30—H301 | 108.3 | C19—C18—H182 | 108.2 |
H302—C30—H301 | 107.3 | H181—C18—H182 | 106.5 |
C30—C31—H312 | 110.0 | C18—C19—H192 | 111.1 |
C30—C31—H311 | 109.5 | C18—C19—H193 | 109.1 |
H312—C31—H311 | 109.2 | H192—C19—H193 | 108.8 |
C30—C31—H313 | 109.5 | C18—C19—H191 | 110.5 |
H312—C31—H313 | 108.9 | H192—C19—H191 | 109.8 |
H311—C31—H313 | 109.7 | H193—C19—H191 | 107.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H261···O4i | 0.97 | 2.38 | 3.261 (3) | 151 |
C35—H351···O4i | 0.97 | 2.54 | 3.344 (3) | 140 |
C31—H312···O1ii | 0.97 | 2.54 | 3.355 (3) | 142 |
O3—H3···N2iii | 0.84 | 1.87 | 2.696 (3) | 168 |
O2—H2···O3 | 0.82 | 2.08 | 2.788 (3) | 143 |
O4—H4···O5 | 0.84 | 1.96 | 2.696 (3) | 147 |
O5—H5···N1iv | 0.83 | 1.90 | 2.713 (3) | 167 |
O1—H1···O3 | 0.79 | 2.07 | 2.777 (3) | 149 |
O6—H6···O5 | 0.83 | 2.07 | 2.810 (3) | 148 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H33NO3 |
Mr | 311.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 13.1922 (2), 22.6174 (5), 13.1144 (3) |
β (°) | 114.447 (1) |
V (Å3) | 3562.17 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.43 × 0.35 × 0.14 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16642, 8498, 5272 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.054, 1.06 |
No. of reflections | 5272 |
No. of parameters | 397 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.18 |
Computer programs: COLLECT (Nonius, 2001)., DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), DIAMOND (Brandenburg & Putz, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H261···O4i | 0.97 | 2.38 | 3.261 (3) | 151 |
C35—H351···O4i | 0.97 | 2.54 | 3.344 (3) | 140 |
C31—H312···O1ii | 0.97 | 2.54 | 3.355 (3) | 142 |
O3—H3···N2iii | 0.84 | 1.87 | 2.696 (3) | 168 |
O2—H2···O3 | 0.82 | 2.08 | 2.788 (3) | 143 |
O4—H4···O5 | 0.84 | 1.96 | 2.696 (3) | 147 |
O5—H5···N1iv | 0.83 | 1.90 | 2.713 (3) | 167 |
O1—H1···O3 | 0.79 | 2.07 | 2.777 (3) | 149 |
O6—H6···O5 | 0.83 | 2.07 | 2.810 (3) | 148 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x−1, y, z. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Recently, an increasing number of molecular receptors based on a polyfunctionalized rigid platform have been reported (Guarise et al., 2006; Haberhauer et al., 2005 ; Li et al., 2005). Among them, adamantane and aza-adamantane scaffolds offer the guarantee of a well-defined environment as a result of axial or equatorial substituent orientation. The title compound shows a perfectly constraint face with three hydroxyl groups in axial positions that could potentially be used, after introduction of suitable ligands, as oriented binding sites for a wide range of applications.
The asymmetric unit of the title compound consists of two independent molecules(A and B) per unit-cell (Z'=2) (Steiner, 2000). This feature arises from the different orientation of one of the propyl group (C11-C12-C13 and C29-C30-C31). Contrary to the case of aza-adamantanone systems which show several C-C bond elongations (Lampkins et al., 2008), all angles and distances within the two molecules agree well with the expected values from the literature (Allen et al., 2006). Each independant molecule of the title compound displays two intra-molecular O-H···O hydrogen bonds and one O-H···N inter-molecular. The later leads to the formation of infinite one-dimensional chains along [2 0 1]. The chains are composed of alternated molecules A and B.