organic compounds
(22E,24R)-5α-Ergosta-2,22-dien-6-one
aDepartment of Pharmaceutical Science, Jinhua Polytechnic, Jinhua 321007, People's Republic of China, and bCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China
*Correspondence e-mail: sheng_l_q@163.com
In the title molecule, C28H44O, two six-membered rings have regular chair conformations, while the six-membered ring containing the C=C double bond exhibits a distorted chair conformation. The five-membered ring adopts an In the crystal, weak intermolecular C—H⋯O interactions link molecules into chains along the b axis. The was assigned to correspond with that of the known chiral centres in a precursor molecule.
Related literature
For details of the synthesis, see: McMorris & Patil (1993). For the of the related compound (22E,24R)-3α,5-cyclo-5α-ergosta-22-en-6-one, see: Sheng et al. (2011).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2008); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536811002388/cv5027sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811002388/cv5027Isup2.hkl
(22E,24R)-5α-Ergosta-2,22-dien-6-one was synthesized as a powder according to the known method (McMorris et al., 1993). Crystals of (I) suitable for structure analysis were obtained by slow evaporation from a mixture of acetone and 95% ethanol (volume proportion, 1:1) as colourless prisms.
C-bound H atoms were placed at calculated positions (C—H 0.95–1.00 Å) and constrained to ride on their parent atoms, withUiso(H) = 1.2-1.5 Ueq(C). Because of negligible
effects, 2305 Friedel pairs were averaged in the The was assigned to correspond with that of the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of the title compound.Data collection: CrystalClear (Rigaku/MSC, 2008); cell
CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of (I) shown with 30% probability displacement ellipsoids. |
C28H44O | F(000) = 440 |
Mr = 396.63 | Dx = 1.100 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3421 reflections |
a = 9.812 (3) Å | θ = 3.2–27.5° |
b = 7.578 (2) Å | µ = 0.06 mm−1 |
c = 16.130 (5) Å | T = 123 K |
β = 92.832 (4)° | Block, colourless |
V = 1197.8 (6) Å3 | 0.58 × 0.34 × 0.33 mm |
Z = 2 |
Rigaku AFC10/Saturn724+ diffractometer | 2598 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.030 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
Detector resolution: 28.5714 pixels mm-1 | h = −12→12 |
phi and ω scans | k = −9→9 |
10906 measured reflections | l = −20→20 |
2908 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0346P)2 + 0.296P] where P = (Fo2 + 2Fc2)/3 |
2908 reflections | (Δ/σ)max < 0.001 |
268 parameters | Δρmax = 0.29 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
C28H44O | V = 1197.8 (6) Å3 |
Mr = 396.63 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.812 (3) Å | µ = 0.06 mm−1 |
b = 7.578 (2) Å | T = 123 K |
c = 16.130 (5) Å | 0.58 × 0.34 × 0.33 mm |
β = 92.832 (4)° |
Rigaku AFC10/Saturn724+ diffractometer | 2598 reflections with I > 2σ(I) |
10906 measured reflections | Rint = 0.030 |
2908 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
2908 reflections | Δρmin = −0.14 e Å−3 |
268 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 | ||
O1 | 0.41104 (19) | −0.0462 (3) | 0.15251 (10) | 0.0498 (5) | |
C1 | 0.5886 (2) | 0.5431 (3) | 0.17436 (13) | 0.0335 (5) | |
H1A | 0.5444 | 0.6606 | 0.1729 | 0.040* | |
H1B | 0.6598 | 0.5438 | 0.2201 | 0.040* | |
C2 | 0.6558 (2) | 0.5130 (4) | 0.09327 (13) | 0.0374 (6) | |
H2 | 0.7045 | 0.6082 | 0.0704 | 0.045* | |
C3 | 0.6508 (2) | 0.3625 (4) | 0.05232 (13) | 0.0378 (6) | |
H3 | 0.6940 | 0.3562 | 0.0010 | 0.045* | |
C4 | 0.5807 (2) | 0.2008 (4) | 0.08234 (13) | 0.0377 (6) | |
H4A | 0.6414 | 0.0975 | 0.0768 | 0.045* | |
H4B | 0.4967 | 0.1797 | 0.0472 | 0.045* | |
C5 | 0.5433 (2) | 0.2187 (3) | 0.17289 (12) | 0.0295 (5) | |
H5 | 0.6303 | 0.2082 | 0.2075 | 0.035* | |
C6 | 0.4516 (2) | 0.0705 (3) | 0.19923 (13) | 0.0332 (5) | |
C7 | 0.4118 (2) | 0.0762 (3) | 0.28843 (13) | 0.0324 (5) | |
H7A | 0.4925 | 0.0480 | 0.3253 | 0.039* | |
H7B | 0.3416 | −0.0150 | 0.2970 | 0.039* | |
C8 | 0.3559 (2) | 0.2571 (3) | 0.31218 (12) | 0.0258 (4) | |
H8 | 0.2648 | 0.2742 | 0.2826 | 0.031* | |
C9 | 0.4513 (2) | 0.4064 (3) | 0.28672 (11) | 0.0243 (4) | |
H9 | 0.5407 | 0.3842 | 0.3174 | 0.029* | |
C10 | 0.4813 (2) | 0.4025 (3) | 0.19277 (12) | 0.0269 (5) | |
C11 | 0.4016 (2) | 0.5869 (3) | 0.31708 (12) | 0.0300 (5) | |
H11A | 0.3167 | 0.6192 | 0.2850 | 0.036* | |
H11B | 0.4712 | 0.6773 | 0.3060 | 0.036* | |
C12 | 0.3740 (2) | 0.5889 (3) | 0.41042 (12) | 0.0280 (5) | |
H12A | 0.4615 | 0.5743 | 0.4430 | 0.034* | |
H12B | 0.3352 | 0.7047 | 0.4250 | 0.034* | |
C13 | 0.27536 (19) | 0.4423 (3) | 0.43412 (11) | 0.0232 (4) | |
C14 | 0.3378 (2) | 0.2678 (3) | 0.40546 (12) | 0.0233 (4) | |
H14 | 0.4318 | 0.2625 | 0.4323 | 0.028* | |
C15 | 0.2560 (2) | 0.1243 (3) | 0.44678 (14) | 0.0361 (5) | |
H15A | 0.3107 | 0.0152 | 0.4548 | 0.043* | |
H15B | 0.1716 | 0.0962 | 0.4132 | 0.043* | |
C16 | 0.2221 (2) | 0.2060 (3) | 0.53128 (13) | 0.0314 (5) | |
H16A | 0.2730 | 0.1444 | 0.5772 | 0.038* | |
H16B | 0.1232 | 0.1960 | 0.5400 | 0.038* | |
C17 | 0.26526 (19) | 0.4034 (3) | 0.52833 (11) | 0.0220 (4) | |
H17 | 0.3596 | 0.4119 | 0.5544 | 0.026* | |
C18 | 0.1323 (2) | 0.4742 (4) | 0.39396 (12) | 0.0391 (6) | |
H18A | 0.1363 | 0.4695 | 0.3334 | 0.059* | |
H18B | 0.0994 | 0.5906 | 0.4104 | 0.059* | |
H18C | 0.0698 | 0.3830 | 0.4124 | 0.059* | |
C19 | 0.3521 (2) | 0.4340 (4) | 0.13685 (12) | 0.0396 (6) | |
H19A | 0.3116 | 0.5477 | 0.1508 | 0.059* | |
H19B | 0.2862 | 0.3393 | 0.1455 | 0.059* | |
H19C | 0.3761 | 0.4349 | 0.0786 | 0.059* | |
C20 | 0.1723 (2) | 0.5195 (3) | 0.57980 (12) | 0.0261 (4) | |
H20 | 0.0767 | 0.5067 | 0.5562 | 0.031* | |
C21 | 0.2101 (2) | 0.7153 (3) | 0.57749 (13) | 0.0337 (5) | |
H21A | 0.1588 | 0.7797 | 0.6184 | 0.051* | |
H21B | 0.1876 | 0.7627 | 0.5220 | 0.051* | |
H21C | 0.3082 | 0.7289 | 0.5906 | 0.051* | |
C22 | 0.17560 (19) | 0.4580 (3) | 0.66901 (11) | 0.0250 (4) | |
H22 | 0.2625 | 0.4501 | 0.6974 | 0.030* | |
C23 | 0.06861 (19) | 0.4144 (3) | 0.71088 (11) | 0.0257 (4) | |
H23 | −0.0176 | 0.4147 | 0.6813 | 0.031* | |
C24 | 0.0705 (2) | 0.3640 (3) | 0.80131 (12) | 0.0247 (4) | |
H24 | 0.1667 | 0.3725 | 0.8245 | 0.030* | |
C25 | −0.0184 (2) | 0.4927 (3) | 0.85049 (13) | 0.0304 (5) | |
H25 | −0.1156 | 0.4767 | 0.8303 | 0.037* | |
C26 | −0.0087 (3) | 0.4528 (4) | 0.94378 (13) | 0.0490 (7) | |
H26A | 0.0863 | 0.4646 | 0.9648 | 0.073* | |
H26B | −0.0402 | 0.3321 | 0.9533 | 0.073* | |
H26C | −0.0660 | 0.5361 | 0.9729 | 0.073* | |
C27 | 0.0205 (3) | 0.6848 (3) | 0.83604 (15) | 0.0375 (6) | |
H27A | −0.0353 | 0.7619 | 0.8694 | 0.056* | |
H27B | 0.0048 | 0.7138 | 0.7771 | 0.056* | |
H27C | 0.1172 | 0.7021 | 0.8523 | 0.056* | |
C28 | 0.0230 (3) | 0.1728 (3) | 0.81002 (14) | 0.0368 (6) | |
H28A | −0.0737 | 0.1638 | 0.7922 | 0.055* | |
H28B | 0.0354 | 0.1360 | 0.8681 | 0.055* | |
H28C | 0.0769 | 0.0961 | 0.7753 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0724 (12) | 0.0452 (11) | 0.0322 (9) | −0.0115 (10) | 0.0075 (8) | −0.0167 (8) |
C1 | 0.0334 (11) | 0.0418 (14) | 0.0261 (11) | 0.0016 (10) | 0.0079 (9) | 0.0050 (9) |
C2 | 0.0312 (11) | 0.0556 (16) | 0.0260 (10) | 0.0020 (11) | 0.0083 (9) | 0.0100 (11) |
C3 | 0.0304 (11) | 0.0628 (18) | 0.0207 (10) | 0.0059 (11) | 0.0053 (9) | 0.0023 (10) |
C4 | 0.0363 (12) | 0.0549 (16) | 0.0222 (10) | 0.0028 (11) | 0.0063 (9) | −0.0067 (10) |
C5 | 0.0288 (11) | 0.0409 (13) | 0.0191 (9) | 0.0024 (10) | 0.0025 (8) | −0.0039 (9) |
C6 | 0.0398 (12) | 0.0349 (13) | 0.0251 (11) | 0.0022 (10) | 0.0033 (9) | −0.0066 (9) |
C7 | 0.0399 (12) | 0.0311 (12) | 0.0268 (10) | −0.0042 (10) | 0.0072 (9) | −0.0064 (9) |
C8 | 0.0255 (10) | 0.0324 (12) | 0.0197 (9) | −0.0005 (9) | 0.0023 (8) | −0.0034 (8) |
C9 | 0.0236 (9) | 0.0301 (11) | 0.0194 (9) | 0.0024 (9) | 0.0020 (7) | 0.0016 (8) |
C10 | 0.0247 (10) | 0.0380 (13) | 0.0183 (9) | 0.0041 (9) | 0.0026 (8) | 0.0001 (8) |
C11 | 0.0364 (11) | 0.0296 (12) | 0.0249 (10) | 0.0058 (10) | 0.0104 (9) | 0.0054 (9) |
C12 | 0.0358 (11) | 0.0239 (11) | 0.0254 (10) | 0.0026 (9) | 0.0111 (9) | 0.0004 (8) |
C13 | 0.0221 (9) | 0.0296 (11) | 0.0181 (8) | 0.0023 (8) | 0.0031 (7) | −0.0011 (8) |
C14 | 0.0246 (10) | 0.0257 (11) | 0.0200 (9) | −0.0045 (8) | 0.0037 (7) | −0.0020 (8) |
C15 | 0.0452 (13) | 0.0335 (13) | 0.0307 (11) | −0.0161 (11) | 0.0128 (10) | −0.0080 (10) |
C16 | 0.0367 (12) | 0.0320 (13) | 0.0262 (10) | −0.0097 (10) | 0.0101 (9) | −0.0033 (9) |
C17 | 0.0211 (9) | 0.0264 (11) | 0.0185 (9) | −0.0014 (8) | 0.0024 (7) | −0.0010 (8) |
C18 | 0.0277 (11) | 0.0665 (18) | 0.0231 (10) | 0.0095 (11) | 0.0013 (8) | 0.0017 (11) |
C19 | 0.0307 (11) | 0.0685 (18) | 0.0196 (9) | 0.0104 (12) | 0.0023 (8) | 0.0052 (11) |
C20 | 0.0207 (9) | 0.0364 (12) | 0.0214 (9) | 0.0020 (9) | 0.0030 (7) | −0.0001 (9) |
C21 | 0.0399 (12) | 0.0331 (12) | 0.0292 (11) | 0.0106 (10) | 0.0110 (9) | 0.0005 (9) |
C22 | 0.0227 (9) | 0.0316 (12) | 0.0206 (9) | 0.0008 (9) | 0.0012 (7) | −0.0043 (8) |
C23 | 0.0254 (10) | 0.0306 (11) | 0.0211 (9) | 0.0010 (9) | 0.0009 (8) | −0.0015 (8) |
C24 | 0.0233 (10) | 0.0306 (12) | 0.0204 (10) | −0.0026 (8) | 0.0026 (8) | −0.0008 (8) |
C25 | 0.0266 (10) | 0.0385 (13) | 0.0266 (10) | −0.0015 (9) | 0.0064 (8) | −0.0039 (9) |
C26 | 0.0652 (16) | 0.0556 (17) | 0.0278 (11) | −0.0009 (15) | 0.0192 (11) | −0.0005 (12) |
C27 | 0.0403 (13) | 0.0354 (13) | 0.0374 (12) | 0.0047 (10) | 0.0066 (10) | −0.0054 (10) |
C28 | 0.0439 (14) | 0.0339 (13) | 0.0326 (12) | −0.0090 (10) | 0.0021 (10) | 0.0014 (10) |
O1—C6 | 1.216 (3) | C15—H15A | 0.9900 |
C1—C2 | 1.511 (3) | C15—H15B | 0.9900 |
C1—C10 | 1.537 (3) | C16—C17 | 1.556 (3) |
C1—H1A | 0.9900 | C16—H16A | 0.9900 |
C1—H1B | 0.9900 | C16—H16B | 0.9900 |
C2—C3 | 1.318 (4) | C17—C20 | 1.539 (3) |
C2—H2 | 0.9500 | C17—H17 | 1.0000 |
C3—C4 | 1.497 (4) | C18—H18A | 0.9800 |
C3—H3 | 0.9500 | C18—H18B | 0.9800 |
C4—C5 | 1.529 (3) | C18—H18C | 0.9800 |
C4—H4A | 0.9900 | C19—H19A | 0.9800 |
C4—H4B | 0.9900 | C19—H19B | 0.9800 |
C5—C6 | 1.513 (3) | C19—H19C | 0.9800 |
C5—C10 | 1.559 (3) | C20—C22 | 1.511 (3) |
C5—H5 | 1.0000 | C20—C21 | 1.530 (3) |
C6—C7 | 1.510 (3) | C20—H20 | 1.0000 |
C7—C8 | 1.532 (3) | C21—H21A | 0.9800 |
C7—H7A | 0.9900 | C21—H21B | 0.9800 |
C7—H7B | 0.9900 | C21—H21C | 0.9800 |
C8—C14 | 1.526 (3) | C22—C23 | 1.318 (3) |
C8—C9 | 1.537 (3) | C22—H22 | 0.9500 |
C8—H8 | 1.0000 | C23—C24 | 1.507 (3) |
C9—C11 | 1.540 (3) | C23—H23 | 0.9500 |
C9—C10 | 1.558 (2) | C24—C28 | 1.531 (3) |
C9—H9 | 1.0000 | C24—C25 | 1.552 (3) |
C10—C19 | 1.538 (3) | C24—H24 | 1.0000 |
C11—C12 | 1.543 (3) | C25—C27 | 1.526 (3) |
C11—H11A | 0.9900 | C25—C26 | 1.533 (3) |
C11—H11B | 0.9900 | C25—H25 | 1.0000 |
C12—C13 | 1.534 (3) | C26—H26A | 0.9800 |
C12—H12A | 0.9900 | C26—H26B | 0.9800 |
C12—H12B | 0.9900 | C26—H26C | 0.9800 |
C13—C18 | 1.536 (3) | C27—H27A | 0.9800 |
C13—C14 | 1.539 (3) | C27—H27B | 0.9800 |
C13—C17 | 1.556 (2) | C27—H27C | 0.9800 |
C14—C15 | 1.525 (3) | C28—H28A | 0.9800 |
C14—H14 | 1.0000 | C28—H28B | 0.9800 |
C15—C16 | 1.548 (3) | C28—H28C | 0.9800 |
C2—C1—C10 | 113.2 (2) | C16—C15—H15A | 111.0 |
C2—C1—H1A | 108.9 | C14—C15—H15B | 111.0 |
C10—C1—H1A | 108.9 | C16—C15—H15B | 111.0 |
C2—C1—H1B | 108.9 | H15A—C15—H15B | 109.0 |
C10—C1—H1B | 108.9 | C15—C16—C17 | 106.68 (16) |
H1A—C1—H1B | 107.7 | C15—C16—H16A | 110.4 |
C3—C2—C1 | 123.9 (2) | C17—C16—H16A | 110.4 |
C3—C2—H2 | 118.0 | C15—C16—H16B | 110.4 |
C1—C2—H2 | 118.0 | C17—C16—H16B | 110.4 |
C2—C3—C4 | 123.5 (2) | H16A—C16—H16B | 108.6 |
C2—C3—H3 | 118.2 | C20—C17—C13 | 119.12 (16) |
C4—C3—H3 | 118.2 | C20—C17—C16 | 111.31 (16) |
C3—C4—C5 | 111.8 (2) | C13—C17—C16 | 104.04 (16) |
C3—C4—H4A | 109.3 | C20—C17—H17 | 107.3 |
C5—C4—H4A | 109.3 | C13—C17—H17 | 107.3 |
C3—C4—H4B | 109.3 | C16—C17—H17 | 107.3 |
C5—C4—H4B | 109.3 | C13—C18—H18A | 109.5 |
H4A—C4—H4B | 107.9 | C13—C18—H18B | 109.5 |
C6—C5—C4 | 112.09 (19) | H18A—C18—H18B | 109.5 |
C6—C5—C10 | 111.21 (16) | C13—C18—H18C | 109.5 |
C4—C5—C10 | 112.96 (19) | H18A—C18—H18C | 109.5 |
C6—C5—H5 | 106.7 | H18B—C18—H18C | 109.5 |
C4—C5—H5 | 106.7 | C10—C19—H19A | 109.5 |
C10—C5—H5 | 106.7 | C10—C19—H19B | 109.5 |
O1—C6—C7 | 121.3 (2) | H19A—C19—H19B | 109.5 |
O1—C6—C5 | 123.2 (2) | C10—C19—H19C | 109.5 |
C7—C6—C5 | 115.59 (18) | H19A—C19—H19C | 109.5 |
C6—C7—C8 | 112.10 (19) | H19B—C19—H19C | 109.5 |
C6—C7—H7A | 109.2 | C22—C20—C21 | 109.17 (18) |
C8—C7—H7A | 109.2 | C22—C20—C17 | 110.62 (17) |
C6—C7—H7B | 109.2 | C21—C20—C17 | 112.97 (17) |
C8—C7—H7B | 109.2 | C22—C20—H20 | 108.0 |
H7A—C7—H7B | 107.9 | C21—C20—H20 | 108.0 |
C14—C8—C7 | 110.76 (18) | C17—C20—H20 | 108.0 |
C14—C8—C9 | 109.04 (16) | C20—C21—H21A | 109.5 |
C7—C8—C9 | 111.18 (16) | C20—C21—H21B | 109.5 |
C14—C8—H8 | 108.6 | H21A—C21—H21B | 109.5 |
C7—C8—H8 | 108.6 | C20—C21—H21C | 109.5 |
C9—C8—H8 | 108.6 | H21A—C21—H21C | 109.5 |
C8—C9—C11 | 111.22 (15) | H21B—C21—H21C | 109.5 |
C8—C9—C10 | 113.13 (17) | C23—C22—C20 | 125.81 (18) |
C11—C9—C10 | 113.82 (17) | C23—C22—H22 | 117.1 |
C8—C9—H9 | 106.0 | C20—C22—H22 | 117.1 |
C11—C9—H9 | 106.0 | C22—C23—C24 | 125.98 (18) |
C10—C9—H9 | 106.0 | C22—C23—H23 | 117.0 |
C1—C10—C19 | 109.40 (19) | C24—C23—H23 | 117.0 |
C1—C10—C9 | 109.81 (17) | C23—C24—C28 | 109.84 (17) |
C19—C10—C9 | 112.18 (15) | C23—C24—C25 | 110.81 (17) |
C1—C10—C5 | 107.53 (16) | C28—C24—C25 | 111.51 (17) |
C19—C10—C5 | 109.67 (19) | C23—C24—H24 | 108.2 |
C9—C10—C5 | 108.13 (16) | C28—C24—H24 | 108.2 |
C9—C11—C12 | 113.11 (18) | C25—C24—H24 | 108.2 |
C9—C11—H11A | 109.0 | C27—C25—C26 | 109.5 (2) |
C12—C11—H11A | 109.0 | C27—C25—C24 | 111.72 (17) |
C9—C11—H11B | 109.0 | C26—C25—C24 | 111.6 (2) |
C12—C11—H11B | 109.0 | C27—C25—H25 | 107.9 |
H11A—C11—H11B | 107.8 | C26—C25—H25 | 107.9 |
C13—C12—C11 | 112.29 (18) | C24—C25—H25 | 107.9 |
C13—C12—H12A | 109.1 | C25—C26—H26A | 109.5 |
C11—C12—H12A | 109.1 | C25—C26—H26B | 109.5 |
C13—C12—H12B | 109.1 | H26A—C26—H26B | 109.5 |
C11—C12—H12B | 109.1 | C25—C26—H26C | 109.5 |
H12A—C12—H12B | 107.9 | H26A—C26—H26C | 109.5 |
C12—C13—C18 | 110.85 (19) | H26B—C26—H26C | 109.5 |
C12—C13—C14 | 106.36 (15) | C25—C27—H27A | 109.5 |
C18—C13—C14 | 112.21 (18) | C25—C27—H27B | 109.5 |
C12—C13—C17 | 116.88 (16) | H27A—C27—H27B | 109.5 |
C18—C13—C17 | 109.92 (15) | C25—C27—H27C | 109.5 |
C14—C13—C17 | 100.14 (16) | H27A—C27—H27C | 109.5 |
C15—C14—C8 | 118.85 (17) | H27B—C27—H27C | 109.5 |
C15—C14—C13 | 104.80 (16) | C24—C28—H28A | 109.5 |
C8—C14—C13 | 114.15 (17) | C24—C28—H28B | 109.5 |
C15—C14—H14 | 106.0 | H28A—C28—H28B | 109.5 |
C8—C14—H14 | 106.0 | C24—C28—H28C | 109.5 |
C13—C14—H14 | 106.0 | H28A—C28—H28C | 109.5 |
C14—C15—C16 | 103.90 (17) | H28B—C28—H28C | 109.5 |
C14—C15—H15A | 111.0 | ||
C10—C1—C2—C3 | −16.3 (3) | C11—C12—C13—C14 | 55.7 (2) |
C1—C2—C3—C4 | −1.6 (4) | C11—C12—C13—C17 | 166.48 (17) |
C2—C3—C4—C5 | −12.2 (3) | C7—C8—C14—C15 | −52.7 (3) |
C3—C4—C5—C6 | 170.17 (19) | C9—C8—C14—C15 | −175.30 (18) |
C3—C4—C5—C10 | 43.6 (2) | C7—C8—C14—C13 | −177.17 (16) |
C4—C5—C6—O1 | −1.4 (3) | C9—C8—C14—C13 | 60.2 (2) |
C10—C5—C6—O1 | 126.1 (2) | C12—C13—C14—C15 | 167.55 (17) |
C4—C5—C6—C7 | 178.9 (2) | C18—C13—C14—C15 | −71.1 (2) |
C10—C5—C6—C7 | −53.6 (2) | C17—C13—C14—C15 | 45.47 (18) |
O1—C6—C7—C8 | −129.2 (2) | C12—C13—C14—C8 | −60.7 (2) |
C5—C6—C7—C8 | 50.5 (3) | C18—C13—C14—C8 | 60.6 (2) |
C6—C7—C8—C14 | −171.04 (17) | C17—C13—C14—C8 | 177.18 (16) |
C6—C7—C8—C9 | −49.7 (2) | C8—C14—C15—C16 | −163.18 (19) |
C14—C8—C9—C11 | −52.8 (2) | C13—C14—C15—C16 | −34.2 (2) |
C7—C8—C9—C11 | −175.21 (17) | C14—C15—C16—C17 | 9.2 (2) |
C14—C8—C9—C10 | 177.62 (16) | C12—C13—C17—C20 | 82.5 (2) |
C7—C8—C9—C10 | 55.2 (2) | C18—C13—C17—C20 | −44.9 (3) |
C2—C1—C10—C19 | −74.4 (2) | C14—C13—C17—C20 | −163.16 (17) |
C2—C1—C10—C9 | 162.09 (17) | C12—C13—C17—C16 | −152.84 (18) |
C2—C1—C10—C5 | 44.7 (2) | C18—C13—C17—C16 | 79.7 (2) |
C8—C9—C10—C1 | −174.10 (17) | C14—C13—C17—C16 | −38.54 (18) |
C11—C9—C10—C1 | 57.7 (2) | C15—C16—C17—C20 | 148.14 (17) |
C8—C9—C10—C19 | 64.0 (2) | C15—C16—C17—C13 | 18.6 (2) |
C11—C9—C10—C19 | −64.2 (2) | C13—C17—C20—C22 | 179.15 (17) |
C8—C9—C10—C5 | −57.0 (2) | C16—C17—C20—C22 | 58.1 (2) |
C11—C9—C10—C5 | 174.73 (17) | C13—C17—C20—C21 | −58.1 (2) |
C6—C5—C10—C1 | 172.97 (17) | C16—C17—C20—C21 | −179.16 (18) |
C4—C5—C10—C1 | −60.0 (2) | C21—C20—C22—C23 | 110.1 (2) |
C6—C5—C10—C19 | −68.2 (2) | C17—C20—C22—C23 | −125.0 (2) |
C4—C5—C10—C19 | 58.9 (2) | C20—C22—C23—C24 | −175.9 (2) |
C6—C5—C10—C9 | 54.5 (2) | C22—C23—C24—C28 | −116.4 (2) |
C4—C5—C10—C9 | −178.51 (17) | C22—C23—C24—C25 | 119.9 (2) |
C8—C9—C11—C12 | 51.5 (2) | C23—C24—C25—C27 | −52.4 (2) |
C10—C9—C11—C12 | −179.31 (17) | C28—C24—C25—C27 | −175.10 (19) |
C9—C11—C12—C13 | −54.1 (2) | C23—C24—C25—C26 | −175.45 (19) |
C11—C12—C13—C18 | −66.5 (2) | C28—C24—C25—C26 | 61.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.99 | 2.59 | 3.574 (3) | 173 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C28H44O |
Mr | 396.63 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 123 |
a, b, c (Å) | 9.812 (3), 7.578 (2), 16.130 (5) |
β (°) | 92.832 (4) |
V (Å3) | 1197.8 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.58 × 0.34 × 0.33 |
Data collection | |
Diffractometer | Rigaku AFC10/Saturn724+ diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10906, 2908, 2598 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.091, 1.03 |
No. of reflections | 2908 |
No. of parameters | 268 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.14 |
Computer programs: CrystalClear (Rigaku/MSC, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.99 | 2.59 | 3.574 (3) | 173 |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
This project was supported by the Science Foudation for Excellent Youth Scholars of the Department of Education of Zhejiang Province (grant No. G0901116050610). The authors acknowledge Professor Kai-bei Yu at the State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, for the data collection.
References
McMorris, T. C. & Patil, P. A. (1993). J. Org. Chem. 58, 2338–2339. CrossRef CAS Web of Science Google Scholar
Rigaku/MSC. (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheng, L., Zeng, F., Chen, F. & Xia, C. (2011). Acta Cryst. E67, o244. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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In continuation of our structural study of brassinolide analogs (Sheng et al., 2011), we present here the crystal structure of the title compound, (I). In (I) (Fig. 1), ring A shows a distorted chair confirmation, and atoms C1, C2, C3 and C4 are coplanar with the r.m.s. deviation of 0.007 (1) Å for the C=C bond; atoms C5 and C10 deviate at 0.329 (4) Å and -0.423 (4) Å from this mean plane, respectively. Rings B and C have regular chair conformation each; while ring D has an envelope conformation. Weak intermolecular C—H···O interactions (Table 1) link the molecules related by translation along the axis b into chains.