organic compounds
4,5,7-Trimethoxy-2-methyl-3-(2,4,5-trimethoxyphenyl)-1-[3-(2,4,5-trimethoxyphenyl)pentan-2-yl]indane acetone 0.858-solvate
aCollege of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, People's Republic of China
*Correspondence e-mail: gyxu@hunnu.edu.cn
In the title compound, C36H48O9.0.858C3H6O, the five-membered ring adopts an The acetone solvent molecule was disordered and was refined over two positions with equal occupancies, giving an overall occupancy of 0.858 (4). There are weak intramolecular C—H⋯O hydrogen bonds and intermolecular C—H⋯π interactions in the structure.
Related literature
For general background, see: Diaz et al. (1993); Hernandez et al. (1993); Menon & Dandiya (1967); Belova et al. (1985); Xu et al. (2009). For related structures, see: Lemini et al. (1990).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809018613/fb2143sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809018613/fb2143Isup2.hkl
In the α-asarone preparation from 2,4,5-trimethoxybenzaldehyde (Xu et al., 2009), the crude product, containing α-asarone, asarone dimers and asarone trimer and other unknown impurities, was dissolved in hot EtOH/H2O (V:V 7:3), and then cooled and filtrated. The yellow powder, obtained by concentrating of the filtrate in vacuo, was dissolved again in EtOH/H2O (V:V 7:3), and then cooled and filtrated. The filtrate afforded a yellow oil after removal of the solvents under reduced pressure. Fifty grams of the yellow oil was subjected to on silica gel and eluted with hexane - ethyl acetate (4:1), the Rf 0.32 fraction was collected and evaporated under vacuum. The residue was crystallized from ethanol to afford the title compound (I). White solid, m.p. 408 K, 1H NMR (CDCl3, p.p.m.): 0.58 (t, 3 H, J = 9.6 Hz), 0.63 (d, 3 H, J = 9.6 Hz), 1.66 (d, 3 H, J = 8.8 Hz), 1.43 (m, 1 H), 1.73 (m, 2 H,), 2.21 (m, 1 H), 2.83 (dd, 1 H, J = 5.6, 7.2 Hz), 3.20 (m, 1 H), 3.44 (s, 3 H), 3.61 (s, 3 H), 3.73 (s, 3 H), 3.77 (s, 3 H), 3.79 (s, 3 H), 3.86 (s, 3 H), 3.86 (s, 3 H), 3.88 (s, 6 H), 4.21 (d, 1 H, J =5.2 Hz), 6.40 (s, 1 H), 6.43 (s, 1 H), 6.48 (s, 1 H), 6.55 (s, 1 H), 6.59 (s, 1 H). 13C NMR (CDCl3, p.p.m.): 12.4, 14.9, 21.0, 26.2, 42.1, 49.3, 49.6, 53.1, 55.1, 56.0, 56.2, 56.4, 56.5, 56.5, 56.6, 56.7, 60.0, 96.5, 97.7, 97.9, 113.0, 125.2, 126.7, 127.0, 139.7, 139.9, 142.5, 142.8, 147.0, 147.5, 151.2, 151.8, 152.4, 152.8. The single crystals were obtained by slow evaporation of the title compound dissolved in acetone at room temperature on the third day.
All the H atoms were placed into the calculated idealized positions, with C—H = 0.98 (methine), 0.97 (methylene), 0.96 (methyl) and 0.93 Å (aryl), and were treated in riding mode approximation. (The methyl groups were checked in the difference electron density maps and allowed to rotate freely about their axes.) Uiso(H)=1.5UeqCmethyl or Uiso(H)=1.3UeqCmethylene/Cmethine/aryl. The acetone solvate appeared to be disordered, and it was refined in two positions. Its occupancy was also refined with assumed equal occupancy at each position because of the proximity of both disordered parts. The following restraints for the disordered acetones have been used: C=O distance was restrained to 1.207 (2) Å; the distances between the neighbour carbons were restrained to 1.344 (2) Å. The displacement parameters of the corresponding atoms were restrained by SIMU 0.05 0.05 for the pairs of the atoms C38A C38B; C39A C39B; O36A O36B; C37A C37B. Moreover the command ISOR 0.05 0.05 was applied for C37A C37B; O36A O36B; C38A C38B C39A C39B (SHELXL-97 (Sheldrick, 2008)).
The
under assumption of stoichiometric ratio of both constituing molecules, i.e. with occupancy equal to 0.5 in each position, gave worse result: _refine_ls_R_factor_all = 0.1087; _refine_ls_R_factor_gt = 0.0582; _refine_ls_wR_factor_ref = 0.1905; _refine_ls_wR_factor_gt = 0.1492; _refine_ls_goodness_of_fit_ref = 1.019; _refine_ls_restrained_S_all = 1.037. Therefore the non-stioichiometric content of the acetone molecule was given the preference.Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C36H4809·0.858C3H6O | Z = 2 |
Mr = 674.57 | F(000) = 727 |
Triclinic, P1 | Dx = 1.207 Mg m−3 |
Hall symbol: -P 1 | Melting point: 408 K |
a = 8.9234 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.2672 (14) Å | Cell parameters from 2731 reflections |
c = 16.3992 (18) Å | θ = 2.5–27.8° |
α = 87.757 (2)° | µ = 0.09 mm−1 |
β = 80.0900 (1)° | T = 298 K |
γ = 76.0220 (1)° | Plate, colourless |
V = 1855.9 (4) Å3 | 0.49 × 0.41 × 0.03 mm |
Bruker APEX area-detector diffractometer | 6438 independent reflections |
Radiation source: fine-focus sealed tube | 3660 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −10→10 |
Tmin = 0.959, Tmax = 0.997 | k = −15→12 |
9730 measured reflections | l = −19→19 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0748P)2 + 0.7819P] where P = (Fo2 + 2Fc2)/3 |
6438 reflections | (Δ/σ)max < 0.001 |
495 parameters | Δρmax = 0.40 e Å−3 |
84 restraints | Δρmin = −0.24 e Å−3 |
C36H4809·0.858C3H6O | γ = 76.0220 (1)° |
Mr = 674.57 | V = 1855.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9234 (10) Å | Mo Kα radiation |
b = 13.2672 (14) Å | µ = 0.09 mm−1 |
c = 16.3992 (18) Å | T = 298 K |
α = 87.757 (2)° | 0.49 × 0.41 × 0.03 mm |
β = 80.0900 (1)° |
Bruker APEX area-detector diffractometer | 6438 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 3660 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.997 | Rint = 0.029 |
9730 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 84 restraints |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.40 e Å−3 |
6438 reflections | Δρmin = −0.24 e Å−3 |
495 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 1.1931 (2) | 0.14498 (15) | 0.22957 (13) | 0.0519 (6) | |
O4 | 0.9453 (3) | 0.25903 (16) | −0.01442 (11) | 0.0510 (6) | |
O2 | 1.1952 (3) | 0.16737 (17) | 0.39503 (14) | 0.0673 (7) | |
O6 | 0.7166 (3) | −0.01714 (17) | 0.20417 (13) | 0.0619 (6) | |
O5 | 0.7116 (3) | −0.03625 (16) | 0.04828 (13) | 0.0601 (6) | |
O9 | 0.0148 (3) | 0.66946 (18) | 0.36065 (14) | 0.0633 (6) | |
O7 | 0.5805 (3) | 0.66492 (16) | 0.15812 (14) | 0.0580 (6) | |
O3 | 0.7466 (3) | 0.46292 (17) | 0.40510 (13) | 0.0604 (6) | |
O8 | 0.1064 (3) | 0.84904 (18) | 0.33474 (16) | 0.0762 (8) | |
C10 | 0.8901 (3) | 0.2026 (2) | 0.12217 (16) | 0.0359 (7) | |
C11 | 0.8868 (3) | 0.1895 (2) | 0.03872 (17) | 0.0386 (7) | |
C2 | 0.8520 (3) | 0.4007 (2) | 0.13985 (17) | 0.0379 (7) | |
H2 | 0.7865 | 0.4008 | 0.0976 | 0.045* | |
C4 | 0.8538 (3) | 0.3652 (2) | 0.28242 (17) | 0.0380 (7) | |
C6 | 1.0852 (3) | 0.2234 (2) | 0.27625 (18) | 0.0420 (7) | |
C18 | 0.3909 (3) | 0.5759 (2) | 0.22003 (17) | 0.0386 (7) | |
C14 | 0.7756 (3) | 0.0537 (2) | 0.15255 (18) | 0.0425 (7) | |
C5 | 0.9700 (3) | 0.2873 (2) | 0.23899 (17) | 0.0371 (7) | |
C17 | 0.4851 (3) | 0.4764 (2) | 0.17502 (17) | 0.0396 (7) | |
H17 | 0.5580 | 0.4977 | 0.1297 | 0.047* | |
C3 | 0.7474 (3) | 0.4266 (2) | 0.22550 (16) | 0.0370 (7) | |
H3 | 0.7293 | 0.5009 | 0.2368 | 0.044* | |
C19 | 0.4390 (4) | 0.6688 (2) | 0.20851 (19) | 0.0449 (7) | |
C16 | 0.5879 (3) | 0.3984 (2) | 0.22794 (17) | 0.0388 (7) | |
H16 | 0.6112 | 0.3307 | 0.2006 | 0.047* | |
C9 | 0.8590 (4) | 0.3818 (2) | 0.36492 (18) | 0.0454 (8) | |
C13 | 0.7717 (3) | 0.0435 (2) | 0.06860 (18) | 0.0430 (7) | |
C8 | 0.9742 (4) | 0.3178 (2) | 0.40316 (19) | 0.0516 (8) | |
H8 | 0.9774 | 0.3290 | 0.4584 | 0.062* | |
C22 | 0.1547 (4) | 0.6702 (2) | 0.30812 (18) | 0.0471 (8) | |
C23 | 0.2479 (3) | 0.5802 (2) | 0.27077 (17) | 0.0422 (7) | |
H23 | 0.2134 | 0.5193 | 0.2800 | 0.051* | |
C1 | 0.9554 (3) | 0.2895 (2) | 0.14877 (16) | 0.0369 (7) | |
H1 | 1.0592 | 0.2851 | 0.1156 | 0.044* | |
C7 | 1.0842 (4) | 0.2374 (2) | 0.36009 (19) | 0.0487 (8) | |
C24 | 0.9528 (4) | 0.4779 (2) | 0.1168 (2) | 0.0527 (8) | |
H24A | 1.0092 | 0.4823 | 0.1609 | 0.079* | |
H24B | 0.8873 | 0.5449 | 0.1080 | 0.079* | |
H24C | 1.0257 | 0.4553 | 0.0671 | 0.079* | |
C12 | 0.8280 (4) | 0.1111 (2) | 0.01227 (18) | 0.0437 (7) | |
H12 | 0.8265 | 0.1040 | −0.0438 | 0.052* | |
C32 | 0.3788 (4) | 0.4259 (3) | 0.1338 (2) | 0.0533 (8) | |
H32A | 0.3224 | 0.3889 | 0.1757 | 0.064* | |
H32B | 0.3021 | 0.4804 | 0.1122 | 0.064* | |
C21 | 0.2052 (4) | 0.7620 (2) | 0.2949 (2) | 0.0539 (9) | |
C28 | 0.9350 (5) | 0.2536 (3) | −0.09955 (19) | 0.0660 (10) | |
H28A | 0.8274 | 0.2628 | −0.1055 | 0.099* | |
H28B | 0.9942 | 0.1871 | −0.1214 | 0.099* | |
H28C | 0.9766 | 0.3074 | −0.1293 | 0.099* | |
C31 | 0.5048 (4) | 0.3847 (3) | 0.31565 (19) | 0.0545 (9) | |
H31A | 0.5683 | 0.3284 | 0.3421 | 0.082* | |
H31B | 0.4057 | 0.3694 | 0.3133 | 0.082* | |
H31C | 0.4880 | 0.4475 | 0.3466 | 0.082* | |
C20 | 0.3467 (4) | 0.7606 (2) | 0.2450 (2) | 0.0529 (8) | |
H20 | 0.3805 | 0.8218 | 0.2357 | 0.063* | |
C29 | 0.7102 (4) | −0.0519 (3) | −0.0364 (2) | 0.0648 (10) | |
H29A | 0.6718 | −0.1123 | −0.0424 | 0.097* | |
H29B | 0.8147 | −0.0616 | −0.0669 | 0.097* | |
H29C | 0.6433 | 0.0077 | −0.0574 | 0.097* | |
C34 | 0.6242 (5) | 0.7593 (3) | 0.1351 (3) | 0.0792 (12) | |
H34A | 0.6383 | 0.7922 | 0.1833 | 0.119* | |
H34B | 0.5435 | 0.8044 | 0.1100 | 0.119* | |
H34C | 0.7205 | 0.7450 | 0.0963 | 0.119* | |
C27 | 0.7729 (6) | 0.4980 (3) | 0.4807 (2) | 0.0951 (15) | |
H27A | 0.6969 | 0.5615 | 0.4973 | 0.143* | |
H27B | 0.8762 | 0.5100 | 0.4735 | 0.143* | |
H27C | 0.7633 | 0.4463 | 0.5227 | 0.143* | |
C33 | 0.4646 (5) | 0.3512 (3) | 0.0641 (2) | 0.0806 (12) | |
H33A | 0.3901 | 0.3262 | 0.0397 | 0.121* | |
H33B | 0.5346 | 0.2937 | 0.0857 | 0.121* | |
H33C | 0.5235 | 0.3864 | 0.0229 | 0.121* | |
C25 | 1.3527 (4) | 0.1453 (3) | 0.2235 (3) | 0.0806 (12) | |
H25A | 1.4164 | 0.0842 | 0.1943 | 0.121* | |
H25B | 1.3781 | 0.1457 | 0.2780 | 0.121* | |
H25C | 1.3722 | 0.2060 | 0.1941 | 0.121* | |
C30 | 0.7076 (5) | −0.0056 (3) | 0.2900 (2) | 0.0758 (11) | |
H30A | 0.6516 | −0.0532 | 0.3191 | 0.114* | |
H30B | 0.6535 | 0.0642 | 0.3062 | 0.114* | |
H30C | 0.8114 | −0.0201 | 0.3032 | 0.114* | |
C35 | 0.1433 (6) | 0.9472 (3) | 0.3104 (3) | 0.0986 (15) | |
H35A | 0.0658 | 1.0025 | 0.3402 | 0.148* | |
H35B | 0.1442 | 0.9571 | 0.2521 | 0.148* | |
H35C | 0.2446 | 0.9473 | 0.3229 | 0.148* | |
C26 | 1.2133 (6) | 0.1858 (3) | 0.4760 (2) | 0.0931 (15) | |
H26A | 1.2986 | 0.1333 | 0.4912 | 0.140* | |
H26B | 1.1187 | 0.1839 | 0.5134 | 0.140* | |
H26C | 1.2352 | 0.2528 | 0.4788 | 0.140* | |
C36 | −0.1154 (5) | 0.6869 (4) | 0.3199 (3) | 0.1014 (15) | |
H36A | −0.2094 | 0.6948 | 0.3601 | 0.152* | |
H36B | −0.1055 | 0.6290 | 0.2844 | 0.152* | |
H36C | −0.1202 | 0.7490 | 0.2873 | 0.152* | |
C15 | 0.8340 (3) | 0.1327 (2) | 0.17745 (18) | 0.0412 (7) | |
H15 | 0.8360 | 0.1394 | 0.2335 | 0.049* | |
C38A | 0.5792 (18) | 0.2552 (10) | 0.5382 (9) | 0.099 (3) | 0.429 (3) |
H38A | 0.5361 | 0.2849 | 0.4905 | 0.148* | 0.429 (3) |
H38B | 0.6648 | 0.2845 | 0.5447 | 0.148* | 0.429 (3) |
H38C | 0.4998 | 0.2700 | 0.5866 | 0.148* | 0.429 (3) |
C39A | 0.7892 (15) | 0.1035 (12) | 0.4803 (9) | 0.123 (4) | 0.429 (3) |
H39A | 0.7878 | 0.1183 | 0.4226 | 0.184* | 0.429 (3) |
H39B | 0.8182 | 0.0297 | 0.4881 | 0.184* | 0.429 (3) |
H39C | 0.8637 | 0.1347 | 0.4989 | 0.184* | 0.429 (3) |
O36A | 0.5576 (11) | 0.0861 (8) | 0.5564 (6) | 0.128 (3) | 0.429 (3) |
C37A | 0.6341 (13) | 0.1455 (9) | 0.5276 (8) | 0.080 (3) | 0.429 (3) |
C38B | 0.5848 (16) | 0.3015 (8) | 0.5510 (8) | 0.089 (3) | 0.429 (3) |
H38D | 0.5885 | 0.3306 | 0.4963 | 0.133* | 0.429 (3) |
H38E | 0.6729 | 0.3104 | 0.5738 | 0.133* | 0.429 (3) |
H38F | 0.4896 | 0.3363 | 0.5855 | 0.133* | 0.429 (3) |
C39B | 0.7096 (19) | 0.1325 (13) | 0.4835 (10) | 0.130 (4) | 0.429 (3) |
H39D | 0.7284 | 0.1757 | 0.4364 | 0.196* | 0.429 (3) |
H39E | 0.6744 | 0.0747 | 0.4671 | 0.196* | 0.429 (3) |
H39F | 0.8048 | 0.1074 | 0.5055 | 0.196* | 0.429 (3) |
O36B | 0.5069 (10) | 0.1506 (7) | 0.5948 (5) | 0.112 (2) | 0.429 (3) |
C37B | 0.5899 (15) | 0.1928 (9) | 0.5469 (7) | 0.073 (3) | 0.429 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0451 (13) | 0.0443 (12) | 0.0616 (14) | 0.0069 (10) | −0.0179 (11) | −0.0153 (10) |
O4 | 0.0677 (15) | 0.0575 (13) | 0.0348 (11) | −0.0266 (11) | −0.0111 (10) | 0.0008 (10) |
O2 | 0.0777 (17) | 0.0596 (14) | 0.0572 (14) | 0.0192 (12) | −0.0394 (13) | −0.0097 (11) |
O6 | 0.0840 (18) | 0.0537 (14) | 0.0529 (14) | −0.0287 (13) | −0.0082 (12) | 0.0035 (11) |
O5 | 0.0794 (17) | 0.0522 (14) | 0.0570 (14) | −0.0287 (12) | −0.0132 (12) | −0.0112 (11) |
O9 | 0.0528 (15) | 0.0731 (16) | 0.0535 (14) | −0.0001 (12) | 0.0002 (12) | −0.0050 (11) |
O7 | 0.0507 (14) | 0.0446 (13) | 0.0778 (16) | −0.0155 (11) | −0.0045 (12) | 0.0095 (11) |
O3 | 0.0615 (15) | 0.0623 (14) | 0.0477 (13) | 0.0129 (12) | −0.0179 (11) | −0.0195 (11) |
O8 | 0.0833 (19) | 0.0445 (14) | 0.0900 (19) | 0.0004 (13) | −0.0031 (15) | −0.0185 (13) |
C10 | 0.0336 (16) | 0.0352 (15) | 0.0363 (16) | 0.0001 (13) | −0.0094 (13) | −0.0045 (12) |
C11 | 0.0367 (17) | 0.0405 (17) | 0.0378 (16) | −0.0071 (13) | −0.0063 (13) | −0.0029 (13) |
C2 | 0.0355 (16) | 0.0386 (16) | 0.0400 (16) | −0.0059 (13) | −0.0115 (13) | −0.0015 (12) |
C4 | 0.0374 (17) | 0.0356 (16) | 0.0417 (17) | −0.0054 (13) | −0.0132 (13) | −0.0013 (12) |
C6 | 0.0410 (18) | 0.0361 (16) | 0.0477 (18) | −0.0001 (14) | −0.0151 (14) | −0.0082 (13) |
C18 | 0.0363 (17) | 0.0353 (16) | 0.0441 (17) | −0.0041 (13) | −0.0130 (14) | 0.0003 (13) |
C14 | 0.0429 (18) | 0.0354 (16) | 0.0464 (18) | −0.0060 (14) | −0.0045 (14) | −0.0002 (13) |
C5 | 0.0379 (17) | 0.0352 (15) | 0.0401 (16) | −0.0074 (13) | −0.0127 (13) | −0.0029 (12) |
C17 | 0.0364 (17) | 0.0402 (16) | 0.0418 (17) | −0.0062 (13) | −0.0096 (13) | −0.0010 (13) |
C3 | 0.0382 (17) | 0.0336 (15) | 0.0392 (16) | −0.0046 (13) | −0.0115 (13) | −0.0032 (12) |
C19 | 0.0442 (19) | 0.0400 (18) | 0.0505 (19) | −0.0064 (15) | −0.0142 (15) | 0.0027 (14) |
C16 | 0.0373 (17) | 0.0349 (15) | 0.0441 (17) | −0.0058 (13) | −0.0100 (13) | −0.0011 (12) |
C9 | 0.0439 (19) | 0.0457 (18) | 0.0437 (18) | −0.0001 (15) | −0.0122 (15) | −0.0091 (14) |
C13 | 0.0429 (18) | 0.0370 (17) | 0.0478 (18) | −0.0055 (14) | −0.0069 (14) | −0.0124 (14) |
C8 | 0.059 (2) | 0.0508 (19) | 0.0417 (17) | 0.0031 (16) | −0.0212 (16) | −0.0084 (14) |
C22 | 0.046 (2) | 0.0473 (19) | 0.0439 (18) | −0.0039 (15) | −0.0071 (15) | −0.0023 (14) |
C23 | 0.0442 (18) | 0.0386 (17) | 0.0435 (17) | −0.0078 (14) | −0.0101 (15) | 0.0016 (13) |
C1 | 0.0331 (16) | 0.0403 (16) | 0.0373 (16) | −0.0069 (13) | −0.0087 (13) | −0.0024 (12) |
C7 | 0.050 (2) | 0.0436 (18) | 0.0519 (19) | 0.0031 (15) | −0.0271 (16) | −0.0030 (14) |
C24 | 0.049 (2) | 0.0476 (19) | 0.060 (2) | −0.0124 (16) | −0.0070 (16) | 0.0039 (15) |
C12 | 0.0497 (19) | 0.0449 (18) | 0.0362 (16) | −0.0094 (15) | −0.0075 (14) | −0.0087 (13) |
C32 | 0.0424 (19) | 0.058 (2) | 0.062 (2) | −0.0067 (16) | −0.0194 (16) | −0.0123 (16) |
C21 | 0.062 (2) | 0.0394 (18) | 0.056 (2) | −0.0003 (16) | −0.0149 (18) | −0.0066 (15) |
C28 | 0.092 (3) | 0.078 (3) | 0.0403 (19) | −0.040 (2) | −0.0183 (19) | 0.0098 (17) |
C31 | 0.044 (2) | 0.058 (2) | 0.058 (2) | −0.0082 (16) | −0.0097 (16) | 0.0134 (16) |
C20 | 0.057 (2) | 0.0379 (18) | 0.066 (2) | −0.0120 (16) | −0.0148 (18) | 0.0027 (15) |
C29 | 0.074 (3) | 0.061 (2) | 0.066 (2) | −0.0199 (19) | −0.018 (2) | −0.0195 (18) |
C34 | 0.071 (3) | 0.059 (2) | 0.110 (3) | −0.029 (2) | −0.005 (2) | 0.013 (2) |
C27 | 0.114 (4) | 0.090 (3) | 0.064 (3) | 0.029 (3) | −0.034 (3) | −0.038 (2) |
C33 | 0.071 (3) | 0.093 (3) | 0.081 (3) | −0.014 (2) | −0.023 (2) | −0.034 (2) |
C25 | 0.050 (2) | 0.088 (3) | 0.099 (3) | −0.002 (2) | −0.013 (2) | −0.025 (2) |
C30 | 0.092 (3) | 0.086 (3) | 0.057 (2) | −0.038 (2) | −0.014 (2) | 0.017 (2) |
C35 | 0.101 (4) | 0.042 (2) | 0.145 (4) | 0.001 (2) | −0.019 (3) | −0.018 (2) |
C26 | 0.113 (4) | 0.088 (3) | 0.071 (3) | 0.022 (3) | −0.058 (3) | −0.011 (2) |
C36 | 0.064 (3) | 0.151 (5) | 0.086 (3) | −0.028 (3) | −0.001 (3) | −0.012 (3) |
C15 | 0.0439 (18) | 0.0403 (17) | 0.0370 (16) | −0.0046 (14) | −0.0071 (14) | −0.0040 (13) |
C38A | 0.104 (4) | 0.099 (5) | 0.092 (4) | −0.017 (4) | −0.024 (3) | 0.003 (4) |
C39A | 0.121 (6) | 0.128 (5) | 0.119 (5) | −0.027 (4) | −0.021 (4) | −0.005 (4) |
O36A | 0.113 (4) | 0.130 (4) | 0.142 (4) | −0.040 (4) | −0.018 (3) | 0.024 (3) |
C37A | 0.078 (4) | 0.081 (4) | 0.077 (4) | −0.017 (4) | −0.013 (3) | 0.011 (4) |
C38B | 0.096 (4) | 0.090 (5) | 0.085 (4) | −0.024 (4) | −0.026 (3) | 0.005 (4) |
C39B | 0.132 (6) | 0.132 (5) | 0.124 (5) | −0.025 (4) | −0.021 (4) | −0.004 (4) |
O36B | 0.104 (4) | 0.120 (4) | 0.122 (4) | −0.053 (3) | −0.018 (3) | 0.010 (3) |
C37B | 0.076 (4) | 0.075 (4) | 0.071 (4) | −0.019 (4) | −0.018 (3) | 0.004 (4) |
O1—C6 | 1.386 (3) | C32—C33 | 1.515 (5) |
O1—C25 | 1.411 (4) | C32—H32A | 0.9700 |
O4—C11 | 1.377 (3) | C32—H32B | 0.9700 |
O4—C28 | 1.420 (3) | C21—C20 | 1.378 (5) |
O2—C7 | 1.372 (3) | C28—H28A | 0.9600 |
O2—C26 | 1.403 (4) | C28—H28B | 0.9600 |
O6—C14 | 1.379 (3) | C28—H28C | 0.9600 |
O6—C30 | 1.408 (4) | C31—H31A | 0.9600 |
O5—C13 | 1.371 (3) | C31—H31B | 0.9600 |
O5—C29 | 1.415 (4) | C31—H31C | 0.9600 |
O9—C22 | 1.391 (4) | C20—H20 | 0.9300 |
O9—C36 | 1.406 (5) | C29—H29A | 0.9600 |
O7—C19 | 1.376 (4) | C29—H29B | 0.9600 |
O7—C34 | 1.418 (4) | C29—H29C | 0.9600 |
O3—C9 | 1.380 (3) | C34—H34A | 0.9600 |
O3—C27 | 1.417 (4) | C34—H34B | 0.9600 |
O8—C21 | 1.380 (4) | C34—H34C | 0.9600 |
O8—C35 | 1.444 (5) | C27—H27A | 0.9600 |
C10—C15 | 1.391 (4) | C27—H27B | 0.9600 |
C10—C11 | 1.393 (4) | C27—H27C | 0.9600 |
C10—C1 | 1.520 (4) | C33—H33A | 0.9600 |
C11—C12 | 1.387 (4) | C33—H33B | 0.9600 |
C2—C24 | 1.516 (4) | C33—H33C | 0.9600 |
C2—C3 | 1.547 (4) | C25—H25A | 0.9600 |
C2—C1 | 1.557 (4) | C25—H25B | 0.9600 |
C2—H2 | 0.9800 | C25—H25C | 0.9600 |
C4—C9 | 1.389 (4) | C30—H30A | 0.9600 |
C4—C5 | 1.391 (4) | C30—H30B | 0.9600 |
C4—C3 | 1.519 (4) | C30—H30C | 0.9600 |
C6—C5 | 1.380 (4) | C35—H35A | 0.9600 |
C6—C7 | 1.393 (4) | C35—H35B | 0.9600 |
C18—C23 | 1.388 (4) | C35—H35C | 0.9600 |
C18—C19 | 1.396 (4) | C26—H26A | 0.9600 |
C18—C17 | 1.523 (4) | C26—H26B | 0.9600 |
C14—C15 | 1.381 (4) | C26—H26C | 0.9600 |
C14—C13 | 1.396 (4) | C36—H36A | 0.9600 |
C5—C1 | 1.506 (4) | C36—H36B | 0.9600 |
C17—C32 | 1.538 (4) | C36—H36C | 0.9600 |
C17—C16 | 1.553 (4) | C15—H15 | 0.9300 |
C17—H17 | 0.9800 | C38A—C37A | 1.426 (11) |
C3—C16 | 1.550 (4) | C38A—H38A | 0.9600 |
C3—H3 | 0.9800 | C38A—H38B | 0.9600 |
C19—C20 | 1.387 (4) | C38A—H38C | 0.9600 |
C16—C31 | 1.527 (4) | C39A—C37A | 1.456 (12) |
C16—H16 | 0.9800 | C39A—H39A | 0.9600 |
C9—C8 | 1.389 (4) | C39A—H39B | 0.9600 |
C13—C12 | 1.379 (4) | C39A—H39C | 0.9600 |
C8—C7 | 1.383 (4) | O36A—C37A | 1.196 (9) |
C8—H8 | 0.9300 | C38B—C37B | 1.436 (11) |
C22—C23 | 1.377 (4) | C38B—H38D | 0.9600 |
C22—C21 | 1.394 (4) | C38B—H38E | 0.9600 |
C23—H23 | 0.9300 | C38B—H38F | 0.9600 |
C1—H1 | 0.9800 | C39B—C37B | 1.459 (12) |
C24—H24A | 0.9600 | C39B—H39D | 0.9600 |
C24—H24B | 0.9600 | C39B—H39E | 0.9600 |
C24—H24C | 0.9600 | C39B—H39F | 0.9600 |
C12—H12 | 0.9300 | O36B—C37B | 1.203 (9) |
C6—O1—C25 | 116.9 (2) | H32A—C32—H32B | 107.6 |
C11—O4—C28 | 117.8 (2) | C20—C21—O8 | 124.7 (3) |
C7—O2—C26 | 118.4 (3) | C20—C21—C22 | 119.4 (3) |
C14—O6—C30 | 117.7 (2) | O8—C21—C22 | 115.8 (3) |
C13—O5—C29 | 117.9 (2) | O4—C28—H28A | 109.5 |
C22—O9—C36 | 113.6 (3) | O4—C28—H28B | 109.5 |
C19—O7—C34 | 118.8 (3) | H28A—C28—H28B | 109.5 |
C9—O3—C27 | 117.6 (2) | O4—C28—H28C | 109.5 |
C21—O8—C35 | 116.2 (3) | H28A—C28—H28C | 109.5 |
C15—C10—C11 | 117.0 (3) | H28B—C28—H28C | 109.5 |
C15—C10—C1 | 123.2 (2) | C16—C31—H31A | 109.5 |
C11—C10—C1 | 119.8 (2) | C16—C31—H31B | 109.5 |
O4—C11—C12 | 123.2 (2) | H31A—C31—H31B | 109.5 |
O4—C11—C10 | 115.5 (2) | C16—C31—H31C | 109.5 |
C12—C11—C10 | 121.3 (3) | H31A—C31—H31C | 109.5 |
C24—C2—C3 | 111.1 (2) | H31B—C31—H31C | 109.5 |
C24—C2—C1 | 110.8 (2) | C21—C20—C19 | 120.5 (3) |
C3—C2—C1 | 105.2 (2) | C21—C20—H20 | 119.7 |
C24—C2—H2 | 109.9 | C19—C20—H20 | 119.7 |
C3—C2—H2 | 109.9 | O5—C29—H29A | 109.5 |
C1—C2—H2 | 109.9 | O5—C29—H29B | 109.5 |
C9—C4—C5 | 118.6 (2) | H29A—C29—H29B | 109.5 |
C9—C4—C3 | 130.2 (3) | O5—C29—H29C | 109.5 |
C5—C4—C3 | 110.9 (2) | H29A—C29—H29C | 109.5 |
C5—C6—O1 | 118.6 (2) | H29B—C29—H29C | 109.5 |
C5—C6—C7 | 118.7 (3) | O7—C34—H34A | 109.5 |
O1—C6—C7 | 122.7 (2) | O7—C34—H34B | 109.5 |
C23—C18—C19 | 116.5 (3) | H34A—C34—H34B | 109.5 |
C23—C18—C17 | 121.5 (3) | O7—C34—H34C | 109.5 |
C19—C18—C17 | 121.8 (3) | H34A—C34—H34C | 109.5 |
O6—C14—C15 | 125.5 (3) | H34B—C34—H34C | 109.5 |
O6—C14—C13 | 115.5 (3) | O3—C27—H27A | 109.5 |
C15—C14—C13 | 119.0 (3) | O3—C27—H27B | 109.5 |
C6—C5—C4 | 122.1 (2) | H27A—C27—H27B | 109.5 |
C6—C5—C1 | 127.1 (3) | O3—C27—H27C | 109.5 |
C4—C5—C1 | 110.7 (2) | H27A—C27—H27C | 109.5 |
C18—C17—C32 | 110.8 (2) | H27B—C27—H27C | 109.5 |
C18—C17—C16 | 114.7 (2) | C32—C33—H33A | 109.5 |
C32—C17—C16 | 112.6 (2) | C32—C33—H33B | 109.5 |
C18—C17—H17 | 106.0 | H33A—C33—H33B | 109.5 |
C32—C17—H17 | 106.0 | C32—C33—H33C | 109.5 |
C16—C17—H17 | 106.0 | H33A—C33—H33C | 109.5 |
C4—C3—C2 | 101.2 (2) | H33B—C33—H33C | 109.5 |
C4—C3—C16 | 116.6 (2) | O1—C25—H25A | 109.5 |
C2—C3—C16 | 110.8 (2) | O1—C25—H25B | 109.5 |
C4—C3—H3 | 109.3 | H25A—C25—H25B | 109.5 |
C2—C3—H3 | 109.3 | O1—C25—H25C | 109.5 |
C16—C3—H3 | 109.3 | H25A—C25—H25C | 109.5 |
O7—C19—C20 | 122.0 (3) | H25B—C25—H25C | 109.5 |
O7—C19—C18 | 116.7 (3) | O6—C30—H30A | 109.5 |
C20—C19—C18 | 121.3 (3) | O6—C30—H30B | 109.5 |
C31—C16—C3 | 113.2 (2) | H30A—C30—H30B | 109.5 |
C31—C16—C17 | 113.7 (2) | O6—C30—H30C | 109.5 |
C3—C16—C17 | 110.2 (2) | H30A—C30—H30C | 109.5 |
C31—C16—H16 | 106.4 | H30B—C30—H30C | 109.5 |
C3—C16—H16 | 106.4 | O8—C35—H35A | 109.5 |
C17—C16—H16 | 106.4 | O8—C35—H35B | 109.5 |
O3—C9—C8 | 123.1 (3) | H35A—C35—H35B | 109.5 |
O3—C9—C4 | 117.1 (2) | O8—C35—H35C | 109.5 |
C8—C9—C4 | 119.8 (3) | H35A—C35—H35C | 109.5 |
O5—C13—C12 | 124.5 (3) | H35B—C35—H35C | 109.5 |
O5—C13—C14 | 115.9 (3) | O2—C26—H26A | 109.5 |
C12—C13—C14 | 119.6 (3) | O2—C26—H26B | 109.5 |
C7—C8—C9 | 120.8 (3) | H26A—C26—H26B | 109.5 |
C7—C8—H8 | 119.6 | O2—C26—H26C | 109.5 |
C9—C8—H8 | 119.6 | H26A—C26—H26C | 109.5 |
C23—C22—O9 | 120.8 (3) | H26B—C26—H26C | 109.5 |
C23—C22—C21 | 119.0 (3) | O9—C36—H36A | 109.5 |
O9—C22—C21 | 120.2 (3) | O9—C36—H36B | 109.5 |
C22—C23—C18 | 123.2 (3) | H36A—C36—H36B | 109.5 |
C22—C23—H23 | 118.4 | O9—C36—H36C | 109.5 |
C18—C23—H23 | 118.4 | H36A—C36—H36C | 109.5 |
C5—C1—C10 | 114.4 (2) | H36B—C36—H36C | 109.5 |
C5—C1—C2 | 101.8 (2) | C14—C15—C10 | 122.7 (3) |
C10—C1—C2 | 114.6 (2) | C14—C15—H15 | 118.6 |
C5—C1—H1 | 108.6 | C10—C15—H15 | 118.6 |
C10—C1—H1 | 108.6 | O36A—C37A—C38A | 122.5 (13) |
C2—C1—H1 | 108.6 | O36A—C37A—C39A | 118.3 (12) |
O2—C7—C8 | 124.0 (3) | C38A—C37A—C39A | 119.2 (11) |
O2—C7—C6 | 116.1 (3) | C37B—C38B—H38D | 109.5 |
C8—C7—C6 | 119.9 (3) | C37B—C38B—H38E | 109.5 |
C2—C24—H24A | 109.5 | H38D—C38B—H38E | 109.5 |
C2—C24—H24B | 109.5 | C37B—C38B—H38F | 109.5 |
H24A—C24—H24B | 109.5 | H38D—C38B—H38F | 109.5 |
C2—C24—H24C | 109.5 | H38E—C38B—H38F | 109.5 |
H24A—C24—H24C | 109.5 | C37B—C39B—H39D | 109.5 |
H24B—C24—H24C | 109.5 | C37B—C39B—H39E | 109.5 |
C13—C12—C11 | 120.4 (3) | H39D—C39B—H39E | 109.5 |
C13—C12—H12 | 119.8 | C37B—C39B—H39F | 109.5 |
C11—C12—H12 | 119.8 | H39D—C39B—H39F | 109.5 |
C33—C32—C17 | 114.5 (3) | H39E—C39B—H39F | 109.5 |
C33—C32—H32A | 108.6 | O36B—C37B—C38B | 123.2 (12) |
C17—C32—H32A | 108.6 | O36B—C37B—C39B | 120.3 (13) |
C33—C32—H32B | 108.6 | C38B—C37B—C39B | 116.4 (11) |
C17—C32—H32B | 108.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O7 | 0.98 | 2.35 | 2.820 (3) | 109 |
C25—H25B···O2 | 0.96 | 2.27 | 2.912 (5) | 123 |
C28—H28A···Cg1i | 0.96 | 2.93 | 3.565 (4) | 125 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C36H4809·0.858C3H6O |
Mr | 674.57 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.9234 (10), 13.2672 (14), 16.3992 (18) |
α, β, γ (°) | 87.757 (2), 80.0900 (1), 76.0220 (1) |
V (Å3) | 1855.9 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.49 × 0.41 × 0.03 |
Data collection | |
Diffractometer | Bruker APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.959, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9730, 6438, 3660 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.174, 1.01 |
No. of reflections | 6438 |
No. of parameters | 495 |
No. of restraints | 84 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.24 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O7 | 0.98 | 2.35 | 2.820 (3) | 108.8 |
C25—H25B···O2 | 0.96 | 2.27 | 2.912 (5) | 123.2 |
C28—H28A···Cg1i | 0.96 | 2.93 | 3.565 (4) | 125 |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
We thank the National Natural Science Foundation of China (grant No. 20602010) and Hunan Provincial Natural Science Foundation of China (grant No. 06JJ50024) for financial support.
References
Belova, L. F., Alibekov, S. D., Baginskaya, A. I., Sokolov, S. Y., Pokrovskaya, G. V., Stikhin, V. A., Trumpe, T. & Gorodnyuk, T. I. (1985). Farmakol. Toksikol. 48, 17–20. CAS PubMed Web of Science Google Scholar
Bruker (1998). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diaz, F., Munoz, H., Labarrios, F., Chamorro, G., Salazar, M., Morelos, M. E. & Tamariz, J. (1993). Med. Chem. Res. 3, 101–109. CAS Google Scholar
Hernandez, A., Lourdes Lopez, M., Chamorro, G. & Mendoza-Figueroa, T. (1993). Planta Med. 59, 121–124. CrossRef CAS PubMed Web of Science Google Scholar
Lemini, C., Mandoki, J. J., Cruz-Almanza, R. & Toscano, R. A. (1990). Acta Cryst. C46, 1542–1545. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Menon, M. K. & Dandiya, P. C. (1967). J. Pharm. Pharmacol. 9, 170–175. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, G., Liu, C., Zhang, W. & Zuo, G. (2009). Org. Prep. Proced. Int. 41, 153–156. CrossRef Google Scholar
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α-Asarone, (III) (Scheme 2), isolated from the Guatteria guameri plant growing in Southeast Mexico, is reported to be an antiplatelet and hypolipidemic agent (Diaz et al., 1993; Hernandez et al., 1993). In addition, it is known to have sedative, neuroleptic, spasmolytic, antiulcerogenic and antiatherogenic activities (Menon & Dandiya, 1967; Belova et al., 1985). As a part of our studies on the optimization of the synthesis of α-asarone (Xu et al., 2009), three by-products, two asarone dimers (Lemini et al., 1990) and the asarone trimer, the title compound (I), were isolated and identified from the crude product. The structure of the asarone dimers was reported by Lemini et al. (1990). In this paper, the structure of the title compound (I) is reported.
As shown in Fig. 1 and Fig. 2, the five-membered ring C4\C3\C5\C1\C2 has an envelope conformation. C4\C3\C5\C1 is nearly planar with the mean deviation of 0.0043 (3) Å and C2 is situated 0.500 (4) Å out of the C4\C3\C5\C1 plane. The benzene ring (C4 to C9) is almost perpendicular to the other two benzene rings (C10 to C15; C18 to C23) with the interplanar angles of 85.05 (9) and 77.58 (7)°, respectively, while the interplanar angle between the benzene rings (C10 to C15 and C18 to C23) equals to 61.31 (10)°. As shown in Fig. 3, the acetone solvate was disordered and it was refined in two positions with equal occupancies giving the overall occupancy 0.858 (4). This means that the content of acetone is lesser than that of asarone trimer, or in other words, that in some unit cells the acetone molecule is not present. The molecular and crystal structure of the title compound is stabilized by intramolecular weak C-H···O hydrogen bonds and C-H···π-ring electron interactions (Table 1).