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organic compounds
Neoline from Aconitum flavum Hand
aFaculty of Biotechnology Industry, Chengdu University, Chengdu 610016, People's Republic of China
*Correspondence e-mail: fzchen7200@163.com
The title compound, C24H39NO6 [systematic name: (1α,6α,14α,16β)-N-ethyl-6,16-dimethoxy-4-methoxymethylaconitane-1,8,14-triol], is a C19-diterpenoid alkaloid from the roots of Aconitum flavum Hand. The molecule has an aconitane carbon skeleton with four six-membered rings and two five-membered rings. Both five-membered rings adopt envelope conformations. Two six-membered rings adopt chair conformations, whereas the other two adopt boat conformations. Intramolecular O—H⋯O and O—H⋯N and intermolecular O—H⋯O hydrogen bonds are present in the structure. In the crystal, one methyl group is disordered over two sites with an occupancy ratio of 0.70 (3):0.30 (3).
Related literature
The title compound is a diterpenoid alkaloid; for the structures of related diterpenoid et al. (2009). The title compound had been previously isolated from the roots of Aconitum carmichaeli Debx, and the chemical structure was established from NMR and MS data, see: Pelletier & Dailey (1976
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009
); program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536811015170/xu5165sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811015170/xu5165Isup2.hkl
The title compound was isolated from the roots of Aconitum flavum Hand. And crystals suitable for X-ray structure analysis were obtained by slow evaporation from an acetone solution at room temperature.
Hydroxy H atoms were located in a difference Fourier map and refined as riding in as-found relative positions with Uiso(H) = 1.5Ueq(O). Other H atoms were located geometrically with C—H = 0.96–0.98 Å and refined with a riding model, Uiso(H) = 1.2 Ueq(C). As no significant anomalous scatterings, Friedel pairs were merged.
Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell
CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008). ![]() | Fig. 1. The molecular structure of the title compound with 30% probabiliy displacement ellipsoids for no-H atoms. H atoms have been omitted clarity. |
C24H39NO6 | F(000) = 952 |
Mr = 437.56 | Dx = 1.227 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7450 reflections |
a = 9.5423 (6) Å | θ = 3.0–29.1° |
b = 13.4727 (9) Å | µ = 0.09 mm−1 |
c = 18.4251 (13) Å | T = 293 K |
V = 2368.7 (3) Å3 | Block, colorless |
Z = 4 | 0.42 × 0.33 × 0.30 mm |
Oxford Diffraction Xcalibur Eos diffractometer | 2130 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.2°, θmin = 3.0° |
Detector resolution: 10.0 pixels mm-1 | h = −11→11 |
ω scans | k = −15→16 |
18153 measured reflections | l = −17→22 |
2422 independent reflections |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1203P)2 + 0.5493P] where P = (Fo2 + 2Fc2)/3 |
2422 reflections | (Δ/σ)max = 0.001 |
295 parameters | Δρmax = 1.02 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C24H39NO6 | V = 2368.7 (3) Å3 |
Mr = 437.56 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.5423 (6) Å | µ = 0.09 mm−1 |
b = 13.4727 (9) Å | T = 293 K |
c = 18.4251 (13) Å | 0.42 × 0.33 × 0.30 mm |
Oxford Diffraction Xcalibur Eos diffractometer | 2130 reflections with I > 2σ(I) |
18153 measured reflections | Rint = 0.027 |
2422 independent reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.02 e Å−3 |
2422 reflections | Δρmin = −0.18 e Å−3 |
295 parameters |
Experimental. Because C19-deterpenoid alkaloids from nature have same absolute configurations, although the configuration can?t be determined by present X-ray analysis, it could be confirmed throng comparison with the analogues of the title compound. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.7798 (3) | 0.62800 (19) | 0.74631 (16) | 0.0520 (7) | |
H1A | 0.8642 | 0.5971 | 0.7583 | 0.078* | |
O2 | 1.0936 (4) | 0.5268 (3) | 0.50259 (19) | 0.0754 (10) | |
O3 | 1.0460 (3) | 0.3044 (2) | 0.6038 (2) | 0.0673 (9) | |
O4 | 0.7543 (3) | 0.16599 (19) | 0.67409 (18) | 0.0569 (8) | |
H4A | 0.6766 | 0.1394 | 0.6562 | 0.085* | |
O5 | 0.4505 (3) | 0.1912 (2) | 0.68421 (17) | 0.0569 (8) | |
H5A | 0.3618 | 0.1850 | 0.7046 | 0.085* | |
O6 | 0.4605 (3) | 0.2734 (2) | 0.85463 (15) | 0.0546 (8) | |
N | 0.9676 (3) | 0.4789 (2) | 0.75691 (18) | 0.0444 (8) | |
C1 | 0.7509 (4) | 0.5921 (3) | 0.6746 (2) | 0.0438 (9) | |
H1 | 0.6516 | 0.6045 | 0.6647 | 0.053* | |
C2 | 0.8354 (5) | 0.6511 (3) | 0.6195 (3) | 0.0511 (10) | |
H2A | 0.8052 | 0.6340 | 0.5708 | 0.061* | |
H2B | 0.8194 | 0.7215 | 0.6267 | 0.061* | |
C3 | 0.9901 (4) | 0.6284 (3) | 0.6280 (3) | 0.0513 (10) | |
H3A | 1.0228 | 0.6564 | 0.6734 | 0.062* | |
H3B | 1.0412 | 0.6604 | 0.5890 | 0.062* | |
C4 | 1.0239 (4) | 0.5152 (3) | 0.6270 (2) | 0.0468 (9) | |
C5 | 0.8907 (4) | 0.4534 (3) | 0.6083 (2) | 0.0401 (8) | |
H5 | 0.8576 | 0.4682 | 0.5591 | 0.048* | |
C6 | 0.9098 (4) | 0.3402 (3) | 0.6191 (2) | 0.0446 (9) | |
H6 | 0.8435 | 0.3058 | 0.5873 | 0.053* | |
C7 | 0.8646 (4) | 0.3216 (3) | 0.6992 (2) | 0.0397 (8) | |
H7 | 0.9377 | 0.2857 | 0.7258 | 0.048* | |
C8 | 0.7251 (4) | 0.2647 (3) | 0.7017 (2) | 0.0411 (8) | |
C9 | 0.6198 (4) | 0.3157 (3) | 0.6503 (2) | 0.0400 (8) | |
H9 | 0.6332 | 0.2918 | 0.6005 | 0.048* | |
C10 | 0.6288 (4) | 0.4310 (3) | 0.6524 (2) | 0.0374 (8) | |
H10 | 0.5943 | 0.4559 | 0.6057 | 0.045* | |
C11 | 0.7761 (4) | 0.4789 (3) | 0.66603 (19) | 0.0353 (8) | |
C12 | 0.5185 (4) | 0.4590 (3) | 0.7114 (2) | 0.0431 (9) | |
H12A | 0.5619 | 0.4980 | 0.7495 | 0.052* | |
H12B | 0.4432 | 0.4976 | 0.6901 | 0.052* | |
C13 | 0.4617 (4) | 0.3614 (3) | 0.7422 (2) | 0.0437 (9) | |
H13 | 0.3642 | 0.3694 | 0.7578 | 0.052* | |
C14 | 0.4700 (4) | 0.2950 (3) | 0.6752 (2) | 0.0454 (9) | |
H14 | 0.4044 | 0.3195 | 0.6384 | 0.054* | |
C15 | 0.6700 (4) | 0.2528 (3) | 0.7800 (2) | 0.0460 (9) | |
H15A | 0.6370 | 0.1851 | 0.7856 | 0.055* | |
H15B | 0.7483 | 0.2615 | 0.8129 | 0.055* | |
C16 | 0.5518 (4) | 0.3230 (3) | 0.8043 (2) | 0.0409 (8) | |
H16 | 0.5941 | 0.3800 | 0.8290 | 0.049* | |
C17 | 0.8417 (4) | 0.4253 (3) | 0.7316 (2) | 0.0378 (8) | |
H17 | 0.7731 | 0.4214 | 0.7711 | 0.045* | |
C18 | 1.1442 (5) | 0.5029 (4) | 0.5726 (3) | 0.0576 (11) | |
H18A | 1.2212 | 0.5466 | 0.5854 | 0.069* | |
H18B | 1.1781 | 0.4351 | 0.5733 | 0.069* | |
C19 | 1.0790 (4) | 0.4814 (3) | 0.7014 (2) | 0.0504 (10) | |
H19A | 1.1196 | 0.4157 | 0.6968 | 0.060* | |
H19B | 1.1525 | 0.5262 | 0.7171 | 0.060* | |
C20 | 1.0242 (5) | 0.4409 (4) | 0.8249 (2) | 0.0631 (12) | |
H20A | 1.1076 | 0.4785 | 0.8370 | 0.076* | |
H20B | 1.0523 | 0.3724 | 0.8177 | 0.076* | |
C21 | 0.9240 (7) | 0.4454 (6) | 0.8884 (3) | 0.095 (2) | |
H21A | 0.8893 | 0.5119 | 0.8936 | 0.143* | |
H21B | 0.9720 | 0.4261 | 0.9319 | 0.143* | |
H21C | 0.8469 | 0.4011 | 0.8799 | 0.143* | |
C22 | 1.2024 (8) | 0.5246 (7) | 0.4501 (4) | 0.124 (3) | |
H22A | 1.2768 | 0.5681 | 0.4649 | 0.185* | |
H22B | 1.1663 | 0.5462 | 0.4041 | 0.185* | |
H22C | 1.2377 | 0.4582 | 0.4457 | 0.185* | |
C23A | 1.0543 (11) | 0.2077 (7) | 0.5829 (9) | 0.089 (5) | 0.70 (3) |
H23A | 0.9977 | 0.1976 | 0.5405 | 0.133* | 0.70 (3) |
H23B | 1.0211 | 0.1658 | 0.6214 | 0.133* | 0.70 (3) |
H23C | 1.1500 | 0.1913 | 0.5721 | 0.133* | 0.70 (3) |
C23B | 1.052 (2) | 0.254 (2) | 0.5398 (13) | 0.075 (8) | 0.30 (3) |
H23D | 1.1433 | 0.2254 | 0.5342 | 0.112* | 0.30 (3) |
H23E | 1.0346 | 0.2995 | 0.5005 | 0.112* | 0.30 (3) |
H23F | 0.9824 | 0.2029 | 0.5396 | 0.112* | 0.30 (3) |
C24 | 0.5239 (7) | 0.2531 (4) | 0.9228 (2) | 0.0751 (15) | |
H24A | 0.5958 | 0.2039 | 0.9166 | 0.113* | |
H24B | 0.4543 | 0.2287 | 0.9559 | 0.113* | |
H24C | 0.5645 | 0.3128 | 0.9418 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0503 (15) | 0.0427 (14) | 0.0629 (17) | 0.0046 (13) | 0.0031 (15) | −0.0123 (13) |
O2 | 0.068 (2) | 0.094 (3) | 0.064 (2) | 0.006 (2) | 0.0269 (18) | 0.0062 (18) |
O3 | 0.0496 (18) | 0.0652 (19) | 0.087 (2) | 0.0161 (16) | 0.0240 (17) | −0.0100 (17) |
O4 | 0.0625 (19) | 0.0354 (14) | 0.0727 (19) | 0.0028 (14) | 0.0122 (16) | −0.0096 (13) |
O5 | 0.0566 (18) | 0.0467 (15) | 0.0675 (19) | −0.0189 (14) | 0.0077 (15) | −0.0066 (13) |
O6 | 0.0521 (17) | 0.0628 (17) | 0.0488 (15) | −0.0125 (15) | 0.0090 (13) | −0.0020 (13) |
N | 0.0336 (16) | 0.0517 (17) | 0.0479 (17) | −0.0041 (15) | −0.0059 (14) | −0.0014 (15) |
C1 | 0.038 (2) | 0.0348 (17) | 0.058 (2) | 0.0039 (16) | 0.0029 (18) | −0.0010 (16) |
C2 | 0.048 (2) | 0.0353 (19) | 0.070 (3) | −0.0028 (18) | 0.004 (2) | 0.0041 (19) |
C3 | 0.045 (2) | 0.045 (2) | 0.064 (3) | −0.0098 (18) | 0.010 (2) | −0.0011 (19) |
C4 | 0.0333 (18) | 0.050 (2) | 0.057 (2) | −0.0019 (18) | 0.0062 (18) | 0.0031 (18) |
C5 | 0.0345 (18) | 0.0416 (19) | 0.0441 (19) | 0.0010 (16) | 0.0041 (15) | 0.0004 (16) |
C6 | 0.0383 (19) | 0.0405 (19) | 0.055 (2) | 0.0029 (17) | 0.0067 (18) | −0.0040 (18) |
C7 | 0.0313 (17) | 0.0379 (18) | 0.050 (2) | 0.0079 (15) | 0.0014 (15) | 0.0056 (16) |
C8 | 0.0393 (19) | 0.0315 (17) | 0.052 (2) | 0.0017 (16) | 0.0057 (17) | −0.0005 (16) |
C9 | 0.0395 (19) | 0.0395 (19) | 0.0410 (19) | −0.0066 (16) | 0.0023 (15) | −0.0056 (16) |
C10 | 0.0327 (18) | 0.0351 (17) | 0.0443 (19) | 0.0006 (15) | −0.0019 (15) | 0.0054 (15) |
C11 | 0.0303 (17) | 0.0340 (17) | 0.0417 (18) | 0.0005 (15) | 0.0017 (15) | 0.0005 (14) |
C12 | 0.0298 (17) | 0.0411 (19) | 0.059 (2) | 0.0032 (16) | 0.0020 (17) | 0.0038 (17) |
C13 | 0.0317 (17) | 0.046 (2) | 0.053 (2) | −0.0043 (17) | 0.0048 (17) | −0.0044 (17) |
C14 | 0.039 (2) | 0.047 (2) | 0.050 (2) | −0.0105 (18) | −0.0013 (17) | 0.0013 (17) |
C15 | 0.046 (2) | 0.0397 (18) | 0.052 (2) | 0.0004 (18) | −0.0017 (18) | 0.0067 (16) |
C16 | 0.0405 (19) | 0.0381 (18) | 0.044 (2) | −0.0064 (16) | 0.0051 (16) | −0.0028 (15) |
C17 | 0.0273 (16) | 0.0372 (17) | 0.049 (2) | 0.0011 (15) | −0.0001 (15) | 0.0019 (16) |
C18 | 0.045 (2) | 0.060 (3) | 0.067 (3) | 0.000 (2) | 0.017 (2) | 0.004 (2) |
C19 | 0.0309 (18) | 0.059 (2) | 0.062 (2) | −0.0050 (18) | −0.0025 (17) | 0.001 (2) |
C20 | 0.052 (2) | 0.080 (3) | 0.057 (3) | −0.009 (2) | −0.016 (2) | 0.008 (2) |
C21 | 0.081 (4) | 0.150 (6) | 0.056 (3) | −0.024 (4) | −0.017 (3) | 0.007 (3) |
C22 | 0.122 (6) | 0.154 (7) | 0.095 (5) | 0.040 (5) | 0.066 (5) | 0.037 (5) |
C23A | 0.089 (6) | 0.062 (5) | 0.115 (11) | 0.026 (5) | 0.034 (6) | −0.007 (6) |
C23B | 0.075 (12) | 0.088 (17) | 0.061 (12) | 0.025 (11) | 0.027 (9) | −0.008 (11) |
C24 | 0.090 (4) | 0.091 (4) | 0.044 (2) | −0.003 (4) | 0.008 (3) | 0.008 (2) |
O1—C1 | 1.434 (5) | C9—H9 | 0.9800 |
O1—H1A | 0.9332 | C10—C12 | 1.559 (5) |
O2—C18 | 1.414 (6) | C10—C11 | 1.566 (5) |
O2—C22 | 1.419 (6) | C10—H10 | 0.9800 |
O3—C23B | 1.359 (17) | C11—C17 | 1.540 (5) |
O3—C23A | 1.361 (9) | C12—C13 | 1.531 (5) |
O3—C6 | 1.415 (5) | C12—H12A | 0.9700 |
O4—C8 | 1.451 (4) | C12—H12B | 0.9700 |
O4—H4A | 0.8861 | C13—C16 | 1.523 (5) |
O5—C14 | 1.421 (5) | C13—C14 | 1.526 (6) |
O5—H5A | 0.9305 | C13—H13 | 0.9800 |
O6—C24 | 1.421 (6) | C14—H14 | 0.9800 |
O6—C16 | 1.437 (4) | C15—C16 | 1.539 (5) |
N—C20 | 1.456 (5) | C15—H15A | 0.9700 |
N—C19 | 1.475 (5) | C15—H15B | 0.9700 |
N—C17 | 1.478 (4) | C16—H16 | 0.9800 |
C1—C2 | 1.521 (6) | C17—H17 | 0.9800 |
C1—C11 | 1.552 (5) | C18—H18A | 0.9700 |
C1—H1 | 0.9800 | C18—H18B | 0.9700 |
C2—C3 | 1.516 (6) | C19—H19A | 0.9700 |
C2—H2A | 0.9700 | C19—H19B | 0.9700 |
C2—H2B | 0.9700 | C20—C21 | 1.512 (8) |
C3—C4 | 1.558 (6) | C20—H20A | 0.9700 |
C3—H3A | 0.9700 | C20—H20B | 0.9700 |
C3—H3B | 0.9700 | C21—H21A | 0.9600 |
C4—C18 | 1.534 (5) | C21—H21B | 0.9600 |
C4—C19 | 1.537 (6) | C21—H21C | 0.9600 |
C4—C5 | 1.559 (5) | C22—H22A | 0.9600 |
C5—C6 | 1.549 (5) | C22—H22B | 0.9600 |
C5—C11 | 1.565 (5) | C22—H22C | 0.9600 |
C5—H5 | 0.9800 | C23A—H23A | 0.9600 |
C6—C7 | 1.558 (5) | C23A—H23B | 0.9600 |
C6—H6 | 0.9800 | C23A—H23C | 0.9600 |
C7—C17 | 1.535 (5) | C23B—H23D | 0.9600 |
C7—C8 | 1.537 (5) | C23B—H23E | 0.9600 |
C7—H7 | 0.9800 | C23B—H23F | 0.9600 |
C8—C9 | 1.543 (5) | C24—H24A | 0.9600 |
C8—C15 | 1.543 (5) | C24—H24B | 0.9600 |
C9—C14 | 1.527 (6) | C24—H24C | 0.9600 |
C9—C10 | 1.556 (5) | ||
C1—O1—H1A | 103.5 | C10—C12—H12A | 110.3 |
C18—O2—C22 | 111.6 (4) | C13—C12—H12B | 110.3 |
C23B—O3—C23A | 43.7 (10) | C10—C12—H12B | 110.3 |
C23B—O3—C6 | 112.4 (9) | H12A—C12—H12B | 108.6 |
C23A—O3—C6 | 115.9 (5) | C16—C13—C14 | 112.3 (3) |
C8—O4—H4A | 109.9 | C16—C13—C12 | 111.8 (3) |
C14—O5—H5A | 104.7 | C14—C13—C12 | 100.7 (3) |
C24—O6—C16 | 113.7 (4) | C16—C13—H13 | 110.6 |
C20—N—C19 | 109.7 (3) | C14—C13—H13 | 110.6 |
C20—N—C17 | 113.7 (3) | C12—C13—H13 | 110.6 |
C19—N—C17 | 112.2 (3) | O5—C14—C13 | 118.4 (3) |
O1—C1—C2 | 109.7 (3) | O5—C14—C9 | 109.7 (3) |
O1—C1—C11 | 113.3 (3) | C13—C14—C9 | 100.7 (3) |
C2—C1—C11 | 111.4 (3) | O5—C14—H14 | 109.2 |
O1—C1—H1 | 107.4 | C13—C14—H14 | 109.2 |
C2—C1—H1 | 107.4 | C9—C14—H14 | 109.2 |
C11—C1—H1 | 107.4 | C16—C15—C8 | 117.2 (3) |
C3—C2—C1 | 110.0 (4) | C16—C15—H15A | 108.0 |
C3—C2—H2A | 109.7 | C8—C15—H15A | 108.0 |
C1—C2—H2A | 109.7 | C16—C15—H15B | 108.0 |
C3—C2—H2B | 109.7 | C8—C15—H15B | 108.0 |
C1—C2—H2B | 109.7 | H15A—C15—H15B | 107.2 |
H2A—C2—H2B | 108.2 | O6—C16—C13 | 107.5 (3) |
C2—C3—C4 | 113.5 (3) | O6—C16—C15 | 110.3 (3) |
C2—C3—H3A | 108.9 | C13—C16—C15 | 113.8 (3) |
C4—C3—H3A | 108.9 | O6—C16—H16 | 108.3 |
C2—C3—H3B | 108.9 | C13—C16—H16 | 108.3 |
C4—C3—H3B | 108.9 | C15—C16—H16 | 108.3 |
H3A—C3—H3B | 107.7 | N—C17—C7 | 116.9 (3) |
C18—C4—C19 | 107.2 (3) | N—C17—C11 | 110.4 (3) |
C18—C4—C3 | 105.5 (3) | C7—C17—C11 | 100.4 (3) |
C19—C4—C3 | 110.6 (4) | N—C17—H17 | 109.6 |
C18—C4—C5 | 114.0 (3) | C7—C17—H17 | 109.6 |
C19—C4—C5 | 108.5 (3) | C11—C17—H17 | 109.6 |
C3—C4—C5 | 110.9 (3) | O2—C18—C4 | 108.5 (4) |
C6—C5—C4 | 113.7 (3) | O2—C18—H18A | 110.0 |
C6—C5—C11 | 102.2 (3) | C4—C18—H18A | 110.0 |
C4—C5—C11 | 107.6 (3) | O2—C18—H18B | 110.0 |
C6—C5—H5 | 111.0 | C4—C18—H18B | 110.0 |
C4—C5—H5 | 111.0 | H18A—C18—H18B | 108.4 |
C11—C5—H5 | 111.0 | N—C19—C4 | 112.2 (3) |
O3—C6—C5 | 114.7 (3) | N—C19—H19A | 109.2 |
O3—C6—C7 | 112.8 (3) | C4—C19—H19A | 109.2 |
C5—C6—C7 | 104.4 (3) | N—C19—H19B | 109.2 |
O3—C6—H6 | 108.2 | C4—C19—H19B | 109.2 |
C5—C6—H6 | 108.2 | H19A—C19—H19B | 107.9 |
C7—C6—H6 | 108.2 | N—C20—C21 | 114.6 (4) |
C17—C7—C8 | 108.6 (3) | N—C20—H20A | 108.6 |
C17—C7—C6 | 105.1 (3) | C21—C20—H20A | 108.6 |
C8—C7—C6 | 110.4 (3) | N—C20—H20B | 108.6 |
C17—C7—H7 | 110.9 | C21—C20—H20B | 108.6 |
C8—C7—H7 | 110.9 | H20A—C20—H20B | 107.6 |
C6—C7—H7 | 110.9 | C20—C21—H21A | 109.5 |
O4—C8—C7 | 106.3 (3) | C20—C21—H21B | 109.5 |
O4—C8—C9 | 108.5 (3) | H21A—C21—H21B | 109.5 |
C7—C8—C9 | 108.9 (3) | C20—C21—H21C | 109.5 |
O4—C8—C15 | 107.3 (3) | H21A—C21—H21C | 109.5 |
C7—C8—C15 | 112.1 (3) | H21B—C21—H21C | 109.5 |
C9—C8—C15 | 113.5 (3) | O2—C22—H22A | 109.5 |
C14—C9—C8 | 110.1 (3) | O2—C22—H22B | 109.5 |
C14—C9—C10 | 103.1 (3) | H22A—C22—H22B | 109.5 |
C8—C9—C10 | 113.2 (3) | O2—C22—H22C | 109.5 |
C14—C9—H9 | 110.1 | H22A—C22—H22C | 109.5 |
C8—C9—H9 | 110.1 | H22B—C22—H22C | 109.5 |
C10—C9—H9 | 110.1 | O3—C23A—H23A | 109.5 |
C9—C10—C12 | 102.8 (3) | O3—C23A—H23B | 109.5 |
C9—C10—C11 | 117.7 (3) | O3—C23A—H23C | 109.5 |
C12—C10—C11 | 113.2 (3) | O3—C23B—H23D | 109.5 |
C9—C10—H10 | 107.6 | O3—C23B—H23E | 109.5 |
C12—C10—H10 | 107.6 | H23D—C23B—H23E | 109.5 |
C11—C10—H10 | 107.6 | O3—C23B—H23F | 109.5 |
C17—C11—C1 | 116.4 (3) | H23D—C23B—H23F | 109.5 |
C17—C11—C5 | 98.4 (3) | H23E—C23B—H23F | 109.5 |
C1—C11—C5 | 113.1 (3) | O6—C24—H24A | 109.5 |
C17—C11—C10 | 107.3 (3) | O6—C24—H24B | 109.5 |
C1—C11—C10 | 106.4 (3) | H24A—C24—H24B | 109.5 |
C5—C11—C10 | 115.3 (3) | O6—C24—H24C | 109.5 |
C13—C12—C10 | 106.9 (3) | H24A—C24—H24C | 109.5 |
C13—C12—H12A | 110.3 | H24B—C24—H24C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N | 0.93 | 1.87 | 2.699 (4) | 146 |
O4—H4A···O5 | 0.89 | 2.33 | 2.925 (4) | 125 |
O5—H5A···O1i | 0.93 | 1.80 | 2.682 (4) | 158 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C24H39NO6 |
Mr | 437.56 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 9.5423 (6), 13.4727 (9), 18.4251 (13) |
V (Å3) | 2368.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.42 × 0.33 × 0.30 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18153, 2422, 2130 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.177, 1.09 |
No. of reflections | 2422 |
No. of parameters | 295 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.02, −0.18 |
Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N | 0.93 | 1.87 | 2.699 (4) | 146 |
O4—H4A···O5 | 0.89 | 2.33 | 2.925 (4) | 125 |
O5—H5A···O1i | 0.93 | 1.80 | 2.682 (4) | 158 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
Acknowledgements
This project was supported by the Scientific Research Fund of Chengdu University, China.
References
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Pelletier, S. W. & Dailey, Z. (1976). J. Am. Chem. Soc. 98, 2626–2632. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, F.-P., Chen, Q.-H. & Liu, X.-Y. (2009). The Alkaloids: Chemistry and Biology, Vol. 67, edited by G. A. Cordell, pp. 1–78. New York: Elsevier. Google Scholar
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.
The title compound of this report, neoline, is a diterpenoid alkaloid and had been previously isolated from the roots of Aconitum carmichaeli Debx. (Pelletier & Dailey, 1976), and its structure was established from the NMR and MS data. The compound itself has analgesic properties, and the plant Aconitum flavum Hand has also been therapeutically used to treatrheumatic pain, paralysis due to stroke, rheumatoid arthritis and some other inflammations. In order to obtain further evidence for the exact configuration and conformation of the title compound, we have here determined its singlecrystal structure. The naming and the rings conforming referred to the literature (Wang et al. 2009). The molecular structure of the title compound is shown in Fig. 1. Six-membered rings A (C1/C2/C3/C4/C5/C11) and D (C8/C9/C14/C13/C16/C15) adopt boat conformations; six-membered ring B (C7/C8/C9/C10/C11/C17) and six-membered N-containing heterocyclic ring E (C4/C5/C11/C17/N1/C19) adopt chair conformations; five-membered rings C (C9/C10/C12/C13/C14) and F (C5/C6/C7/C17/C11) adopt envelope conformations. The crystal structure contains intermolecular O–H···O and O–H···N hydrogen bonds (Table 1).