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The title compound, C
18H
26ClNO
2, is one of a group of decahydroisoquinoline derivatives that are known to exhibit a diverse range of bioactivities. The piperidine and cyclohexanone rings exist in chair conformations and form a
cis-fused decalin-type bicyclic framework. In the crystal structure, infinite zigzag chains oriented along the
b axis are formed by O—H
O intermolecular hydrogen bonds.
Supporting information
CCDC reference: 251636
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.027
- wR factor = 0.080
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg.
Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.56
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.20 Ratio
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Diffractometer Program (Schagen et al., 1988); cell refinement: CAD-4 Diffractometer Program; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
4a-Hydroxy-2,3,8a-trimethyl-6-oxo-8-phenylperhydroisoquinolinium chloride
top
Crystal data top
C18H26NO2+·Cl− | F(000) = 696 |
Mr = 323.85 | Dx = 1.299 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 24 reflections |
a = 15.149 (3) Å | θ = 11.2–12.5° |
b = 9.339 (2) Å | µ = 0.24 mm−1 |
c = 12.227 (2) Å | T = 293 K |
β = 106.87 (3)° | Prism, colorless |
V = 1655.4 (6) Å3 | 0.56 × 0.48 × 0.25 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.022 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.6° |
Beta-filtr monochromator | h = −17→17 |
θ–2θ scans | k = 0→11 |
3059 measured reflections | l = 0→14 |
2906 independent reflections | 3 standard reflections every 60 min |
2215 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | All H-atom parameters refined |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.3033P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2906 reflections | Δρmax = 0.26 e Å−3 |
304 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0052 (15) |
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 | |
Cl | 0.21793 (3) | 0.55396 (4) | 0.73158 (3) | 0.04566 (15) | |
O1 | 0.05574 (7) | 0.09716 (12) | 0.39197 (10) | 0.0448 (3) | |
O2 | 0.13413 (8) | 0.51566 (12) | 0.21999 (8) | 0.0374 (3) | |
N | 0.22680 (8) | 0.65309 (11) | 0.49371 (9) | 0.0281 (3) | |
C1 | 0.25988 (9) | 0.32102 (13) | 0.49221 (10) | 0.0252 (3) | |
C2 | 0.21056 (10) | 0.17613 (15) | 0.46015 (13) | 0.0323 (3) | |
C3 | 0.11411 (9) | 0.18180 (14) | 0.38285 (12) | 0.0318 (3) | |
C4 | 0.09605 (11) | 0.28855 (16) | 0.28780 (13) | 0.0364 (3) | |
C5 | 0.14031 (9) | 0.43537 (14) | 0.32175 (10) | 0.0282 (3) | |
C6 | 0.24451 (9) | 0.42393 (13) | 0.38670 (10) | 0.0257 (3) | |
C7 | 0.08934 (9) | 0.51636 (15) | 0.39385 (12) | 0.0301 (3) | |
C8 | 0.12614 (9) | 0.66626 (14) | 0.42597 (11) | 0.0303 (3) | |
C9 | 0.28006 (9) | 0.57465 (14) | 0.42600 (12) | 0.0286 (3) | |
C10 | 0.27040 (13) | 0.79530 (16) | 0.52894 (14) | 0.0427 (4) | |
C11 | 0.29910 (11) | 0.37380 (19) | 0.30560 (13) | 0.0372 (3) | |
C12 | 0.07191 (12) | 0.74594 (19) | 0.49346 (14) | 0.0424 (4) | |
C13 | 0.36135 (9) | 0.29724 (14) | 0.55594 (11) | 0.0289 (3) | |
C14 | 0.41478 (10) | 0.19452 (17) | 0.52200 (14) | 0.0415 (4) | |
C15 | 0.50648 (11) | 0.17394 (19) | 0.58294 (16) | 0.0492 (4) | |
C16 | 0.54663 (11) | 0.2542 (2) | 0.67854 (15) | 0.0480 (4) | |
C17 | 0.49528 (11) | 0.3564 (2) | 0.71274 (15) | 0.0475 (4) | |
C18 | 0.40331 (10) | 0.37718 (17) | 0.65263 (12) | 0.0367 (3) | |
H1N | 0.2285 (11) | 0.6063 (19) | 0.5587 (15) | 0.041 (4)* | |
H2O | 0.0796 (15) | 0.537 (2) | 0.1930 (17) | 0.053 (6)* | |
H1 | 0.2332 (9) | 0.3680 (15) | 0.5474 (11) | 0.020 (3)* | |
H21 | 0.2407 (11) | 0.1227 (19) | 0.4182 (14) | 0.039 (4)* | |
H22 | 0.2096 (12) | 0.123 (2) | 0.5290 (16) | 0.049 (5)* | |
H41 | 0.0333 (12) | 0.3016 (17) | 0.2527 (13) | 0.035 (4)* | |
H42 | 0.1199 (13) | 0.252 (2) | 0.2279 (17) | 0.055 (5)* | |
H71 | 0.0251 (11) | 0.5210 (16) | 0.3494 (13) | 0.033 (4)* | |
H72 | 0.0898 (10) | 0.4656 (16) | 0.4631 (14) | 0.031 (4)* | |
H8 | 0.1277 (10) | 0.7191 (16) | 0.3585 (13) | 0.028 (3)* | |
H91 | 0.3439 (11) | 0.5705 (15) | 0.4716 (13) | 0.027 (3)* | |
H92 | 0.2741 (10) | 0.6342 (18) | 0.3619 (14) | 0.036 (4)* | |
H101 | 0.3362 (13) | 0.7748 (19) | 0.5636 (15) | 0.045 (5)* | |
H102 | 0.2612 (13) | 0.853 (2) | 0.4608 (17) | 0.060 (5)* | |
H103 | 0.2436 (12) | 0.837 (2) | 0.5840 (16) | 0.050 (5)* | |
H111 | 0.3642 (13) | 0.3763 (18) | 0.3423 (14) | 0.042 (4)* | |
H112 | 0.2852 (12) | 0.276 (2) | 0.2832 (15) | 0.048 (5)* | |
H113 | 0.2841 (12) | 0.4311 (19) | 0.2383 (16) | 0.047 (5)* | |
H121 | 0.0844 (13) | 0.702 (2) | 0.5704 (18) | 0.060 (5)* | |
H122 | 0.0052 (14) | 0.736 (2) | 0.4541 (17) | 0.058 (5)* | |
H123 | 0.0870 (14) | 0.842 (3) | 0.4987 (17) | 0.064 (6)* | |
H14 | 0.3863 (12) | 0.139 (2) | 0.4526 (16) | 0.052 (5)* | |
H15 | 0.5430 (14) | 0.103 (2) | 0.5585 (16) | 0.058 (5)* | |
H16 | 0.6078 (13) | 0.2332 (19) | 0.7177 (15) | 0.048 (5)* | |
H17 | 0.5224 (14) | 0.413 (2) | 0.7775 (18) | 0.062 (6)* | |
H18 | 0.3680 (12) | 0.4452 (19) | 0.6786 (14) | 0.042 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0654 (3) | 0.0434 (2) | 0.0324 (2) | 0.00636 (18) | 0.02091 (17) | 0.00811 (15) |
O1 | 0.0366 (6) | 0.0404 (6) | 0.0573 (7) | −0.0095 (5) | 0.0137 (5) | −0.0069 (5) |
O2 | 0.0390 (6) | 0.0460 (6) | 0.0239 (5) | 0.0070 (5) | 0.0036 (4) | 0.0075 (4) |
N | 0.0379 (6) | 0.0224 (5) | 0.0225 (5) | −0.0016 (5) | 0.0063 (5) | 0.0016 (4) |
C1 | 0.0276 (6) | 0.0229 (6) | 0.0236 (6) | 0.0008 (5) | 0.0051 (5) | −0.0021 (5) |
C2 | 0.0360 (7) | 0.0247 (7) | 0.0334 (7) | −0.0006 (6) | 0.0056 (6) | −0.0018 (6) |
C3 | 0.0338 (7) | 0.0253 (7) | 0.0363 (7) | −0.0023 (6) | 0.0101 (6) | −0.0114 (6) |
C4 | 0.0323 (8) | 0.0374 (8) | 0.0324 (7) | −0.0023 (6) | −0.0022 (6) | −0.0071 (6) |
C5 | 0.0310 (7) | 0.0291 (7) | 0.0214 (6) | 0.0012 (5) | 0.0028 (5) | 0.0003 (5) |
C6 | 0.0283 (7) | 0.0259 (7) | 0.0220 (6) | 0.0014 (5) | 0.0062 (5) | −0.0003 (5) |
C7 | 0.0261 (7) | 0.0326 (7) | 0.0296 (7) | 0.0033 (6) | 0.0049 (5) | 0.0037 (6) |
C8 | 0.0362 (7) | 0.0289 (7) | 0.0246 (6) | 0.0072 (6) | 0.0069 (6) | 0.0034 (5) |
C9 | 0.0293 (7) | 0.0288 (7) | 0.0272 (7) | −0.0016 (5) | 0.0075 (6) | 0.0031 (5) |
C10 | 0.0605 (11) | 0.0265 (7) | 0.0378 (8) | −0.0089 (7) | 0.0091 (8) | −0.0032 (7) |
C11 | 0.0398 (9) | 0.0432 (9) | 0.0309 (8) | 0.0057 (7) | 0.0139 (7) | −0.0013 (7) |
C12 | 0.0511 (10) | 0.0405 (9) | 0.0368 (8) | 0.0142 (8) | 0.0147 (7) | 0.0003 (7) |
C13 | 0.0290 (7) | 0.0267 (7) | 0.0288 (6) | 0.0005 (5) | 0.0052 (5) | 0.0037 (5) |
C14 | 0.0354 (8) | 0.0388 (8) | 0.0449 (9) | 0.0087 (6) | 0.0033 (7) | −0.0058 (7) |
C15 | 0.0374 (8) | 0.0457 (9) | 0.0631 (11) | 0.0134 (7) | 0.0123 (8) | 0.0031 (8) |
C16 | 0.0272 (7) | 0.0607 (11) | 0.0496 (9) | 0.0029 (7) | 0.0010 (7) | 0.0112 (8) |
C17 | 0.0364 (8) | 0.0596 (11) | 0.0387 (9) | −0.0047 (8) | −0.0015 (7) | −0.0036 (8) |
C18 | 0.0330 (7) | 0.0400 (8) | 0.0333 (7) | 0.0004 (6) | 0.0035 (6) | −0.0027 (6) |
Geometric parameters (Å, º) top
O1—C3 | 1.2150 (17) | C8—C12 | 1.518 (2) |
O2—C5 | 1.4323 (16) | C8—H8 | 0.967 (15) |
O2—H2O | 0.82 (2) | C9—H91 | 0.967 (16) |
N—C10 | 1.4902 (18) | C9—H92 | 0.943 (17) |
N—C9 | 1.5035 (17) | C10—H101 | 0.982 (18) |
N—C8 | 1.5144 (18) | C10—H102 | 0.97 (2) |
N—H1N | 0.901 (18) | C10—H103 | 0.965 (19) |
C1—C13 | 1.5246 (19) | C11—H111 | 0.958 (18) |
C1—C2 | 1.5405 (18) | C11—H112 | 0.96 (2) |
C1—C6 | 1.5709 (17) | C11—H113 | 0.952 (19) |
C1—H1 | 0.984 (14) | C12—H121 | 0.99 (2) |
C2—C3 | 1.493 (2) | C12—H122 | 0.99 (2) |
C2—H21 | 0.926 (17) | C12—H123 | 0.93 (2) |
C2—H22 | 0.980 (19) | C13—C18 | 1.387 (2) |
C3—C4 | 1.495 (2) | C13—C14 | 1.394 (2) |
C4—C5 | 1.530 (2) | C14—C15 | 1.386 (2) |
C4—H41 | 0.930 (17) | C14—H14 | 0.979 (19) |
C4—H42 | 0.97 (2) | C15—C16 | 1.373 (3) |
C5—C7 | 1.5299 (19) | C15—H15 | 0.97 (2) |
C5—C6 | 1.5512 (19) | C16—C17 | 1.371 (3) |
C6—C9 | 1.5336 (18) | C16—H16 | 0.932 (19) |
C6—C11 | 1.5370 (19) | C17—C18 | 1.387 (2) |
C7—C8 | 1.516 (2) | C17—H17 | 0.94 (2) |
C7—H71 | 0.968 (16) | C18—H18 | 0.943 (18) |
C7—H72 | 0.968 (16) | | |
| | | |
C5—O2—H2O | 106.4 (14) | N—C8—C12 | 111.13 (12) |
C10—N—C9 | 109.25 (12) | C7—C8—C12 | 112.17 (13) |
C10—N—C8 | 112.16 (11) | N—C8—H8 | 103.8 (8) |
C9—N—C8 | 110.76 (10) | C7—C8—H8 | 110.4 (9) |
C10—N—H1N | 106.3 (11) | C12—C8—H8 | 111.4 (8) |
C9—N—H1N | 111.5 (11) | N—C9—C6 | 115.08 (11) |
C8—N—H1N | 106.7 (11) | N—C9—H91 | 108.0 (9) |
C13—C1—C2 | 110.17 (11) | C6—C9—H91 | 110.2 (8) |
C13—C1—C6 | 113.33 (11) | N—C9—H92 | 103.5 (9) |
C2—C1—C6 | 112.52 (11) | C6—C9—H92 | 109.9 (10) |
C13—C1—H1 | 105.5 (8) | H91—C9—H92 | 109.9 (13) |
C2—C1—H1 | 107.5 (8) | N—C10—H101 | 105.1 (10) |
C6—C1—H1 | 107.3 (8) | N—C10—H102 | 107.8 (12) |
C3—C2—C1 | 116.31 (11) | H101—C10—H102 | 110.8 (16) |
C3—C2—H21 | 102.6 (10) | N—C10—H103 | 108.9 (11) |
C1—C2—H21 | 109.5 (10) | H101—C10—H103 | 111.0 (15) |
C3—C2—H22 | 107.8 (11) | H102—C10—H103 | 112.9 (16) |
C1—C2—H22 | 110.5 (11) | C6—C11—H111 | 111.3 (10) |
H21—C2—H22 | 109.7 (14) | C6—C11—H112 | 111.1 (11) |
O1—C3—C2 | 121.56 (13) | H111—C11—H112 | 105.6 (15) |
O1—C3—C4 | 122.09 (13) | C6—C11—H113 | 110.4 (11) |
C2—C3—C4 | 116.13 (12) | H111—C11—H113 | 110.2 (15) |
C3—C4—C5 | 114.82 (11) | H112—C11—H113 | 108.1 (15) |
C3—C4—H41 | 112.2 (10) | C8—C12—H121 | 109.1 (11) |
C5—C4—H41 | 108.4 (10) | C8—C12—H122 | 109.1 (11) |
C3—C4—H42 | 109.1 (11) | H121—C12—H122 | 108.0 (16) |
C5—C4—H42 | 107.0 (11) | C8—C12—H123 | 110.6 (13) |
H41—C4—H42 | 104.7 (14) | H121—C12—H123 | 111.2 (17) |
O2—C5—C7 | 108.97 (11) | H122—C12—H123 | 108.8 (17) |
O2—C5—C4 | 108.69 (11) | C18—C13—C14 | 117.53 (13) |
C7—C5—C4 | 110.16 (12) | C18—C13—C1 | 120.14 (12) |
O2—C5—C6 | 106.32 (11) | C14—C13—C1 | 122.32 (12) |
C7—C5—C6 | 110.35 (10) | C15—C14—C13 | 120.89 (15) |
C4—C5—C6 | 112.21 (11) | C15—C14—H14 | 120.9 (11) |
C9—C6—C11 | 106.02 (11) | C13—C14—H14 | 118.2 (11) |
C9—C6—C5 | 108.05 (10) | C16—C15—C14 | 120.63 (16) |
C11—C6—C5 | 110.42 (11) | C16—C15—H15 | 119.1 (12) |
C9—C6—C1 | 110.44 (10) | C14—C15—H15 | 120.3 (12) |
C11—C6—C1 | 111.35 (11) | C17—C16—C15 | 119.28 (15) |
C5—C6—C1 | 110.42 (11) | C17—C16—H16 | 123.8 (11) |
C8—C7—C5 | 113.37 (11) | C15—C16—H16 | 116.9 (11) |
C8—C7—H71 | 109.8 (9) | C16—C17—C18 | 120.50 (16) |
C5—C7—H71 | 106.9 (9) | C16—C17—H17 | 119.9 (13) |
C8—C7—H72 | 108.5 (9) | C18—C17—H17 | 119.6 (13) |
C5—C7—H72 | 112.6 (9) | C17—C18—C13 | 121.17 (15) |
H71—C7—H72 | 105.3 (13) | C17—C18—H18 | 119.8 (10) |
N—C8—C7 | 107.63 (10) | C13—C18—H18 | 119.0 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···Cl | 0.901 (18) | 2.219 (18) | 3.0921 (13) | 162.8 (15) |
O2—H2O···O1i | 0.82 (2) | 2.09 (2) | 2.9055 (17) | 173.9 (19) |
Symmetry code: (i) −x, y+1/2, −z+1/2. |
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