Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047307/av3110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047307/av3110Isup2.hkl |
CCDC reference: 667262
The isolated halotolerant fungal strain THW-18, was isolated from the sediments collected in Hongdao salt field, Qingdao, China. The working strain was cultured under static conditions at 303 K for 45 days in two hundred and fifty 1000-ml conical flasks containing the liquid medium (300 ml/flask) composed of maltose (8 g/L), mannitol (8 g/L), glucose (4 g/L), monosodium glutamate (10 g/L), KH2PO4 (0.5 g/L), yeast extract paste (3 g/L), maize paste (1 g/L), and sea salt (100 g/L) after adjusting its pH to 6.5. The fermented whole broth (75 L) was filtered through cheese cloth to separate into supernatant and mycelia. The mycelia were extracted three times with acetone and the acetone solution was concentrated under reduced pressure to afford crude extract (42 g). The crude extract, which was subjected to chromatography over silica gel column using a stepwise gradient elution of petroleum ether-CHCl3—MeOH, to yield five fractions (Fr.1-Fr.5). Fr.2 was subjected to Sephadex LH-20 eluting with CHCl3—MeOH (1:1), followed by chromatographing on a silica gel column eluting with CHCl3—MeOH (30:1) to afford three subfractions (Fr.2–2-1-Fr.2–2-3). The title compound (23 mg) was purified by extensive preparative HPLC using MeOH-H2O (9:1) from Fr.2–2-2. The single crystals were obtained by slow evaporation of a petroleum ether-acetone (1:1) solution at room temperature on the third day.
All H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of 0.93–0.98 (C—H) and 0.82 Å (O—H), and with Uiso(H) values of 1.2Ueq(C) and 1.5Ueq(Cmethyl, O). As mentioned above, the absolute configuration could not be determined crystallographically and Friedel pairs were merged.
Dimethylincisterol A3, (I), was first reported as an intermediate to synthesize the (17R)-17-methylincisterol (De Riccardis et al., 1995), and then was isolated from a marine sponge Homaxinella sp. in 2005 (Mansoor et al., 2005). This title compound and related compounds are of interest because of their biological activities (Togashi et al., 1998; Mansoor et al., 2005; Kawagishi et al., 2006). We isolated (I) as a part of our ongoing study characterizing bioactive metabolites from various halotolerant microorganisms. This is our first report about the title compound isolated from halotolerant fungus THW-18 and the results of its X-ray crystallographic study (Fig. 1).
The five-membered N3—C4—C5—C6—C7 ring adopts a twist conformation, and the six-membered N2—C3—C4—N3—C8—C9 ring adopts a half-chair conformation. The corresponding puckering parameters (Cremer & Pople, 1975) are Q = 0.462 (4) Å, φ = 192.5 (5)° and Q = 0.564 (4) Å, θ = 6.1 (4)°, φ = 264 (3)°.
It was not possible to determined the absolute configuration of compound (I) by anomalous dispersion effects, but the positive optical rotation suggested that this compound was dimethylincisterol A3 (Mansoor et al., 2005; Kawagishi et al., 2006).
As shown in Fig. 2, the compounds are linked into a 1-D ribbon along [010] by the O3—H3A···O2i hydrogen bond. (symmetry code: i = 3 - x, 1/2 + y, 1 - z).
For general background, see: Mansoor et al. (2005); Togashi et al. (1998); Kawagishi et al. (2006); De Riccardis et al. (1995). For related literature, see: Cremer & Pople (1975).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H32O3 | F(000) = 364 |
Mr = 332.47 | Dx = 1.080 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0506 (9) Å | Cell parameters from 2840 reflections |
b = 6.7640 (8) Å | θ = 2.3–22.1° |
c = 18.858 (2) Å | µ = 0.07 mm−1 |
β = 95.639 (2)° | T = 298 K |
V = 1021.9 (2) Å3 | Flake, colourless |
Z = 2 | 0.56 × 0.51 × 0.18 mm |
Bruker APEX area-detector diffractometer | 1965 independent reflections |
Radiation source: fine-focus sealed tube | 1247 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.962, Tmax = 0.988 | k = −8→8 |
5311 measured reflections | l = −22→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0482P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1965 reflections | Δρmax = 0.13 e Å−3 |
224 parameters | Δρmin = −0.15 e Å−3 |
1 restraint | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
C21H32O3 | V = 1021.9 (2) Å3 |
Mr = 332.47 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.0506 (9) Å | µ = 0.07 mm−1 |
b = 6.7640 (8) Å | T = 298 K |
c = 18.858 (2) Å | 0.56 × 0.51 × 0.18 mm |
β = 95.639 (2)° |
Bruker APEX area-detector diffractometer | 1965 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1247 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.988 | Rint = 0.049 |
5311 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | Δρmax = 0.13 e Å−3 |
S = 1.05 | Δρmin = −0.15 e Å−3 |
1965 reflections | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881. |
224 parameters | Absolute structure parameter: 0 (10) |
1 restraint |
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 | ||
O1 | 1.4534 (3) | 0.2461 (4) | 0.46674 (13) | 0.0650 (8) | |
O2 | 1.4101 (3) | 0.2856 (5) | 0.58115 (15) | 0.0768 (9) | |
O3 | 1.4982 (3) | 0.4173 (5) | 0.36379 (13) | 0.0699 (8) | |
H3 | 1.5217 | 0.5222 | 0.3842 | 0.105* | |
C1 | 1.3731 (4) | 0.3295 (6) | 0.5192 (2) | 0.0601 (10) | |
C2 | 1.2432 (4) | 0.4584 (6) | 0.48848 (19) | 0.0558 (10) | |
H2 | 1.1721 | 0.5330 | 0.5138 | 0.067* | |
C3 | 1.2414 (4) | 0.4536 (5) | 0.41862 (18) | 0.0471 (9) | |
C4 | 1.3778 (4) | 0.3200 (6) | 0.39805 (19) | 0.0526 (10) | |
C5 | 1.3090 (4) | 0.1516 (6) | 0.3518 (2) | 0.0615 (11) | |
H5A | 1.2516 | 0.0595 | 0.3804 | 0.074* | |
H5B | 1.4002 | 0.0816 | 0.3330 | 0.074* | |
C6 | 1.1873 (4) | 0.2264 (6) | 0.28980 (18) | 0.0576 (10) | |
H6A | 1.2492 | 0.3018 | 0.2574 | 0.069* | |
H6B | 1.1380 | 0.1137 | 0.2638 | 0.069* | |
C7 | 1.0479 (4) | 0.3558 (5) | 0.31402 (17) | 0.0447 (8) | |
C8 | 1.1314 (4) | 0.5317 (5) | 0.35810 (18) | 0.0462 (9) | |
H8 | 1.2034 | 0.5999 | 0.3270 | 0.055* | |
C9 | 0.9890 (4) | 0.6699 (6) | 0.36851 (19) | 0.0589 (10) | |
H9A | 1.0285 | 0.8045 | 0.3760 | 0.071* | |
H9B | 0.9309 | 0.6295 | 0.4088 | 0.071* | |
C10 | 0.8755 (4) | 0.6518 (6) | 0.29844 (19) | 0.0601 (10) | |
H10A | 0.8795 | 0.7724 | 0.2709 | 0.072* | |
H10B | 0.7610 | 0.6289 | 0.3082 | 0.072* | |
C11 | 0.9407 (4) | 0.4739 (5) | 0.25643 (17) | 0.0515 (9) | |
H11 | 1.0169 | 0.5279 | 0.2239 | 0.062* | |
C12 | 0.7992 (4) | 0.3695 (6) | 0.21038 (19) | 0.0614 (11) | |
H12 | 0.7251 | 0.3099 | 0.2427 | 0.074* | |
C13 | 0.6990 (5) | 0.5150 (7) | 0.16491 (19) | 0.0665 (11) | |
H13 | 0.7526 | 0.5764 | 0.1294 | 0.080* | |
C14 | 0.5453 (5) | 0.5652 (7) | 0.1695 (2) | 0.0693 (12) | |
H14 | 0.4914 | 0.4964 | 0.2033 | 0.083* | |
C15 | 0.4421 (5) | 0.7175 (7) | 0.1283 (2) | 0.0797 (14) | |
H15 | 0.5070 | 0.7697 | 0.0912 | 0.096* | |
C16 | 0.2811 (6) | 0.6235 (10) | 0.0917 (3) | 0.1076 (19) | |
H16 | 0.2198 | 0.5626 | 0.1285 | 0.129* | |
C17 | 0.1679 (7) | 0.7832 (14) | 0.0527 (3) | 0.172 (3) | |
H17A | 0.2280 | 0.8488 | 0.0180 | 0.258* | |
H17B | 0.1358 | 0.8781 | 0.0867 | 0.258* | |
H17C | 0.0699 | 0.7216 | 0.0293 | 0.258* | |
C18 | 0.9365 (4) | 0.2377 (6) | 0.35926 (19) | 0.0560 (10) | |
H18A | 0.9008 | 0.1185 | 0.3346 | 0.084* | |
H18B | 0.8406 | 0.3154 | 0.3677 | 0.084* | |
H18C | 0.9977 | 0.2047 | 0.4039 | 0.084* | |
C19 | 0.8610 (6) | 0.2045 (7) | 0.1650 (2) | 0.0952 (16) | |
H19A | 0.7688 | 0.1507 | 0.1350 | 0.143* | |
H19B | 0.9110 | 0.1024 | 0.1953 | 0.143* | |
H19C | 0.9424 | 0.2563 | 0.1359 | 0.143* | |
C20 | 0.4074 (8) | 0.8880 (10) | 0.1784 (3) | 0.145 (3) | |
H20A | 0.3362 | 0.8424 | 0.2130 | 0.217* | |
H20B | 0.3535 | 0.9941 | 0.1512 | 0.217* | |
H20C | 0.5108 | 0.9343 | 0.2024 | 0.217* | |
C21 | 0.3219 (7) | 0.4647 (13) | 0.0398 (3) | 0.155 (3) | |
H21A | 0.3817 | 0.5221 | 0.0033 | 0.233* | |
H21B | 0.2204 | 0.4061 | 0.0185 | 0.233* | |
H21C | 0.3896 | 0.3649 | 0.0646 | 0.233* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0597 (15) | 0.0751 (19) | 0.0595 (15) | 0.0205 (16) | 0.0030 (13) | −0.0023 (15) |
O2 | 0.0836 (18) | 0.089 (2) | 0.0568 (16) | 0.0033 (17) | 0.0014 (14) | 0.0036 (16) |
O3 | 0.0504 (14) | 0.095 (2) | 0.0679 (17) | −0.0066 (15) | 0.0228 (13) | −0.0126 (15) |
C1 | 0.055 (2) | 0.064 (3) | 0.061 (3) | −0.003 (2) | 0.007 (2) | −0.004 (2) |
C2 | 0.053 (2) | 0.058 (2) | 0.058 (2) | 0.004 (2) | 0.0127 (18) | −0.009 (2) |
C3 | 0.0423 (18) | 0.045 (2) | 0.055 (2) | −0.0029 (18) | 0.0094 (17) | −0.005 (2) |
C4 | 0.0448 (19) | 0.058 (2) | 0.056 (2) | 0.008 (2) | 0.0100 (18) | −0.002 (2) |
C5 | 0.059 (2) | 0.058 (2) | 0.068 (2) | 0.014 (2) | 0.007 (2) | −0.019 (2) |
C6 | 0.057 (2) | 0.056 (2) | 0.060 (2) | 0.010 (2) | 0.0078 (19) | −0.012 (2) |
C7 | 0.0447 (18) | 0.040 (2) | 0.0503 (19) | 0.0036 (17) | 0.0103 (17) | 0.0011 (17) |
C8 | 0.0440 (18) | 0.044 (2) | 0.053 (2) | −0.0012 (18) | 0.0121 (17) | 0.0024 (18) |
C9 | 0.064 (2) | 0.040 (2) | 0.072 (3) | 0.008 (2) | 0.005 (2) | −0.001 (2) |
C10 | 0.067 (2) | 0.051 (2) | 0.062 (2) | 0.008 (2) | 0.007 (2) | 0.003 (2) |
C11 | 0.055 (2) | 0.052 (2) | 0.049 (2) | 0.001 (2) | 0.0124 (17) | 0.006 (2) |
C12 | 0.061 (2) | 0.068 (3) | 0.055 (2) | 0.001 (2) | 0.002 (2) | 0.001 (2) |
C13 | 0.064 (2) | 0.087 (3) | 0.049 (2) | 0.005 (3) | 0.007 (2) | 0.011 (2) |
C14 | 0.062 (3) | 0.092 (3) | 0.054 (2) | 0.003 (3) | 0.005 (2) | 0.012 (2) |
C15 | 0.077 (3) | 0.104 (4) | 0.059 (3) | 0.017 (3) | 0.011 (2) | 0.010 (3) |
C16 | 0.077 (3) | 0.162 (6) | 0.082 (3) | 0.027 (4) | −0.002 (3) | 0.020 (4) |
C17 | 0.127 (5) | 0.234 (9) | 0.146 (5) | 0.070 (7) | −0.028 (4) | 0.012 (7) |
C18 | 0.058 (2) | 0.045 (2) | 0.066 (2) | −0.0025 (19) | 0.010 (2) | 0.005 (2) |
C19 | 0.108 (3) | 0.092 (4) | 0.080 (3) | 0.015 (3) | −0.020 (3) | −0.022 (3) |
C20 | 0.180 (6) | 0.135 (6) | 0.117 (4) | 0.070 (5) | 0.005 (4) | −0.031 (4) |
C21 | 0.148 (5) | 0.170 (7) | 0.136 (5) | 0.034 (6) | −0.046 (4) | −0.051 (6) |
O1—C1 | 1.357 (4) | C11—H11 | 0.9800 |
O1—C4 | 1.464 (4) | C12—C13 | 1.490 (5) |
O2—C1 | 1.213 (4) | C12—C19 | 1.520 (5) |
O3—C4 | 1.383 (4) | C12—H12 | 0.9800 |
O3—H3 | 0.8200 | C13—C14 | 1.294 (5) |
C1—C2 | 1.439 (5) | C13—H13 | 0.9300 |
C2—C3 | 1.317 (4) | C14—C15 | 1.493 (6) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C8 | 1.472 (4) | C15—C20 | 1.534 (7) |
C3—C4 | 1.503 (5) | C15—C16 | 1.544 (7) |
C4—C5 | 1.507 (5) | C15—H15 | 0.9800 |
C5—C6 | 1.536 (5) | C16—C21 | 1.512 (8) |
C5—H5A | 0.9700 | C16—C17 | 1.551 (9) |
C5—H5B | 0.9700 | C16—H16 | 0.9800 |
C6—C7 | 1.528 (4) | C17—H17A | 0.9600 |
C6—H6A | 0.9700 | C17—H17B | 0.9600 |
C6—H6B | 0.9700 | C17—H17C | 0.9600 |
C7—C18 | 1.524 (5) | C18—H18A | 0.9600 |
C7—C11 | 1.542 (5) | C18—H18B | 0.9600 |
C7—C8 | 1.565 (5) | C18—H18C | 0.9600 |
C8—C9 | 1.507 (5) | C19—H19A | 0.9600 |
C8—H8 | 0.9800 | C19—H19B | 0.9600 |
C9—C10 | 1.536 (4) | C19—H19C | 0.9600 |
C9—H9A | 0.9700 | C20—H20A | 0.9600 |
C9—H9B | 0.9700 | C20—H20B | 0.9600 |
C10—C11 | 1.560 (5) | C20—H20C | 0.9600 |
C10—H10A | 0.9700 | C21—H21A | 0.9600 |
C10—H10B | 0.9700 | C21—H21B | 0.9600 |
C11—C12 | 1.535 (5) | C21—H21C | 0.9600 |
C1—O1—C4 | 108.5 (3) | C7—C11—H11 | 107.0 |
C4—O3—H3 | 109.5 | C10—C11—H11 | 107.0 |
O2—C1—O1 | 120.7 (4) | C13—C12—C19 | 110.5 (3) |
O2—C1—C2 | 129.5 (4) | C13—C12—C11 | 110.6 (3) |
O1—C1—C2 | 109.7 (3) | C19—C12—C11 | 113.0 (3) |
C3—C2—C1 | 108.9 (3) | C13—C12—H12 | 107.5 |
C3—C2—H2 | 125.5 | C19—C12—H12 | 107.5 |
C1—C2—H2 | 125.5 | C11—C12—H12 | 107.5 |
C2—C3—C8 | 135.5 (3) | C14—C13—C12 | 127.0 (4) |
C2—C3—C4 | 109.7 (3) | C14—C13—H13 | 116.5 |
C8—C3—C4 | 114.5 (3) | C12—C13—H13 | 116.5 |
O3—C4—O1 | 109.0 (3) | C13—C14—C15 | 129.3 (4) |
O3—C4—C3 | 113.4 (3) | C13—C14—H14 | 115.4 |
O1—C4—C3 | 103.2 (3) | C15—C14—H14 | 115.4 |
O3—C4—C5 | 108.9 (3) | C14—C15—C20 | 108.9 (3) |
O1—C4—C5 | 110.6 (3) | C14—C15—C16 | 110.4 (4) |
C3—C4—C5 | 111.6 (3) | C20—C15—C16 | 112.9 (4) |
C4—C5—C6 | 111.2 (3) | C14—C15—H15 | 108.2 |
C4—C5—H5A | 109.4 | C20—C15—H15 | 108.2 |
C6—C5—H5A | 109.4 | C16—C15—H15 | 108.2 |
C4—C5—H5B | 109.4 | C21—C16—C15 | 110.8 (4) |
C6—C5—H5B | 109.4 | C21—C16—C17 | 110.1 (5) |
H5A—C5—H5B | 108.0 | C15—C16—C17 | 110.7 (6) |
C7—C6—C5 | 113.2 (3) | C21—C16—H16 | 108.4 |
C7—C6—H6A | 108.9 | C15—C16—H16 | 108.4 |
C5—C6—H6A | 108.9 | C17—C16—H16 | 108.4 |
C7—C6—H6B | 108.9 | C16—C17—H17A | 109.5 |
C5—C6—H6B | 108.9 | C16—C17—H17B | 109.5 |
H6A—C6—H6B | 107.8 | H17A—C17—H17B | 109.5 |
C18—C7—C6 | 110.9 (3) | C16—C17—H17C | 109.5 |
C18—C7—C11 | 110.2 (3) | H17A—C17—H17C | 109.5 |
C6—C7—C11 | 117.6 (3) | H17B—C17—H17C | 109.5 |
C18—C7—C8 | 110.3 (3) | C7—C18—H18A | 109.5 |
C6—C7—C8 | 107.7 (2) | C7—C18—H18B | 109.5 |
C11—C7—C8 | 99.3 (3) | H18A—C18—H18B | 109.5 |
C3—C8—C9 | 121.9 (3) | C7—C18—H18C | 109.5 |
C3—C8—C7 | 109.5 (3) | H18A—C18—H18C | 109.5 |
C9—C8—C7 | 104.4 (2) | H18B—C18—H18C | 109.5 |
C3—C8—H8 | 106.7 | C12—C19—H19A | 109.5 |
C9—C8—H8 | 106.7 | C12—C19—H19B | 109.5 |
C7—C8—H8 | 106.7 | H19A—C19—H19B | 109.5 |
C8—C9—C10 | 103.6 (3) | C12—C19—H19C | 109.5 |
C8—C9—H9A | 111.0 | H19A—C19—H19C | 109.5 |
C10—C9—H9A | 111.0 | H19B—C19—H19C | 109.5 |
C8—C9—H9B | 111.0 | C15—C20—H20A | 109.5 |
C10—C9—H9B | 111.0 | C15—C20—H20B | 109.5 |
H9A—C9—H9B | 109.0 | H20A—C20—H20B | 109.5 |
C9—C10—C11 | 107.3 (3) | C15—C20—H20C | 109.5 |
C9—C10—H10A | 110.3 | H20A—C20—H20C | 109.5 |
C11—C10—H10A | 110.3 | H20B—C20—H20C | 109.5 |
C9—C10—H10B | 110.3 | C16—C21—H21A | 109.5 |
C11—C10—H10B | 110.3 | C16—C21—H21B | 109.5 |
H10A—C10—H10B | 108.5 | H21A—C21—H21B | 109.5 |
C12—C11—C7 | 119.6 (3) | C16—C21—H21C | 109.5 |
C12—C11—C10 | 112.0 (3) | H21A—C21—H21C | 109.5 |
C7—C11—C10 | 103.6 (3) | H21B—C21—H21C | 109.5 |
C12—C11—H11 | 107.0 | ||
C4—O1—C1—O2 | 177.5 (3) | C11—C7—C8—C3 | 179.2 (2) |
C4—O1—C1—C2 | 0.3 (4) | C18—C7—C8—C9 | −68.6 (3) |
O2—C1—C2—C3 | −176.2 (4) | C6—C7—C8—C9 | 170.2 (3) |
O1—C1—C2—C3 | 0.7 (4) | C11—C7—C8—C9 | 47.1 (3) |
C1—C2—C3—C8 | 172.0 (4) | C3—C8—C9—C10 | −160.2 (3) |
C1—C2—C3—C4 | −1.4 (4) | C7—C8—C9—C10 | −35.8 (4) |
C1—O1—C4—O3 | 119.8 (3) | C8—C9—C10—C11 | 10.5 (4) |
C1—O1—C4—C3 | −1.1 (4) | C18—C7—C11—C12 | −48.5 (4) |
C1—O1—C4—C5 | −120.5 (3) | C6—C7—C11—C12 | 79.9 (4) |
C2—C3—C4—O3 | −116.3 (4) | C8—C7—C11—C12 | −164.4 (3) |
C8—C3—C4—O3 | 68.8 (4) | C18—C7—C11—C10 | 76.9 (3) |
C2—C3—C4—O1 | 1.5 (4) | C6—C7—C11—C10 | −154.6 (3) |
C8—C3—C4—O1 | −173.4 (3) | C8—C7—C11—C10 | −38.9 (3) |
C2—C3—C4—C5 | 120.3 (3) | C9—C10—C11—C12 | 148.9 (3) |
C8—C3—C4—C5 | −54.7 (4) | C9—C10—C11—C7 | 18.7 (4) |
O3—C4—C5—C6 | −76.4 (4) | C7—C11—C12—C13 | 172.9 (3) |
O1—C4—C5—C6 | 163.7 (3) | C10—C11—C12—C13 | 51.6 (4) |
C3—C4—C5—C6 | 49.5 (4) | C7—C11—C12—C19 | −62.7 (4) |
C4—C5—C6—C7 | −53.5 (4) | C10—C11—C12—C19 | 176.0 (3) |
C5—C6—C7—C18 | −64.2 (4) | C19—C12—C13—C14 | 121.2 (5) |
C5—C6—C7—C11 | 167.6 (3) | C11—C12—C13—C14 | −112.9 (5) |
C5—C6—C7—C8 | 56.6 (4) | C12—C13—C14—C15 | 176.2 (4) |
C2—C3—C8—C9 | 7.5 (6) | C13—C14—C15—C20 | −111.3 (6) |
C4—C3—C8—C9 | −179.3 (3) | C13—C14—C15—C16 | 124.2 (5) |
C2—C3—C8—C7 | −114.6 (5) | C14—C15—C16—C21 | −61.1 (6) |
C4—C3—C8—C7 | 58.7 (4) | C20—C15—C16—C21 | 176.7 (5) |
C18—C7—C8—C3 | 63.4 (3) | C14—C15—C16—C17 | 176.5 (4) |
C6—C7—C8—C3 | −57.8 (3) | C20—C15—C16—C17 | 54.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 1.96 | 2.771 (4) | 171 |
Symmetry code: (i) −x+3, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H32O3 |
Mr | 332.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 8.0506 (9), 6.7640 (8), 18.858 (2) |
β (°) | 95.639 (2) |
V (Å3) | 1021.9 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.56 × 0.51 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.962, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5311, 1965, 1247 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.113, 1.05 |
No. of reflections | 1965 |
No. of parameters | 224 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.15 |
Absolute structure | Flack, H. D. (1983). Acta Cryst. A39, 876–881. |
Absolute structure parameter | 0 (10) |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), WinGX (Farrugia, 1999).
O1—C1 | 1.357 (4) | O3—C4 | 1.383 (4) |
O1—C4 | 1.464 (4) | O3—H3 | 0.8200 |
O2—C1 | 1.213 (4) | C13—C14 | 1.294 (5) |
C1—O1—C4 | 108.5 (3) | C18—C7—C8 | 110.3 (3) |
C4—O3—H3 | 109.5 | C6—C7—C8 | 107.7 (2) |
O2—C1—O1 | 120.7 (4) | C11—C7—C8 | 99.3 (3) |
C2—C3—C8 | 135.5 (3) | C3—C8—C9 | 121.9 (3) |
C2—C3—C4 | 109.7 (3) | C3—C8—C7 | 109.5 (3) |
O3—C4—O1 | 109.0 (3) | C9—C8—C7 | 104.4 (2) |
O1—C4—C3 | 103.2 (3) | C14—C13—C12 | 127.0 (4) |
O1—C4—C5 | 110.6 (3) | C14—C13—H13 | 116.5 |
C18—C7—C6 | 110.9 (3) | C12—C13—H13 | 116.5 |
C18—C7—C11 | 110.2 (3) | C13—C14—C15 | 129.3 (4) |
C6—C7—C11 | 117.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 1.96 | 2.771 (4) | 171 |
Symmetry code: (i) −x+3, y+1/2, −z+1. |
Dimethylincisterol A3, (I), was first reported as an intermediate to synthesize the (17R)-17-methylincisterol (De Riccardis et al., 1995), and then was isolated from a marine sponge Homaxinella sp. in 2005 (Mansoor et al., 2005). This title compound and related compounds are of interest because of their biological activities (Togashi et al., 1998; Mansoor et al., 2005; Kawagishi et al., 2006). We isolated (I) as a part of our ongoing study characterizing bioactive metabolites from various halotolerant microorganisms. This is our first report about the title compound isolated from halotolerant fungus THW-18 and the results of its X-ray crystallographic study (Fig. 1).
The five-membered N3—C4—C5—C6—C7 ring adopts a twist conformation, and the six-membered N2—C3—C4—N3—C8—C9 ring adopts a half-chair conformation. The corresponding puckering parameters (Cremer & Pople, 1975) are Q = 0.462 (4) Å, φ = 192.5 (5)° and Q = 0.564 (4) Å, θ = 6.1 (4)°, φ = 264 (3)°.
It was not possible to determined the absolute configuration of compound (I) by anomalous dispersion effects, but the positive optical rotation suggested that this compound was dimethylincisterol A3 (Mansoor et al., 2005; Kawagishi et al., 2006).
As shown in Fig. 2, the compounds are linked into a 1-D ribbon along [010] by the O3—H3A···O2i hydrogen bond. (symmetry code: i = 3 - x, 1/2 + y, 1 - z).