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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jan 8;67(Pt 2):o244. doi: 10.1107/S1600536810052906

(22E,24R)-3α,5-Cyclo-5α-ergosta-22-en-6-one

Liu-qing Sheng a,*, Fang Zeng b, Fei Chen a, Chun-nian Xia b
PMCID: PMC3051649  PMID: 21522938

Abstract

In the title mol­ecule, C28H44O, the two six-membered rings have a chair conformation and the two five-membered rings haveenvelope conformations. The crystal packing exhibits no short inter­molecular contacts. The absolute configuration 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.

Related literature

Many analogues of brassinolide as plant regulators have been isolated from a wide variety of plants, and many attempts have been undertaken to synthesize these brassinosteroids, see, for example: Aburatani et al. (1987 ▶); Brosa et al. (2001 ▶); Brosa & Santamarta (1999 ▶); McMorris et al. (1993 ▶); Clouse (1996 ▶, 2002 ▶). For related structures, see: Chen et al. (2009 ▶); Xia et al. (2005 ▶).graphic file with name e-67-0o244-scheme1.jpg

Experimental

Crystal data

  • C28H44O

  • M r = 396.63

  • Orthorhombic, Inline graphic

  • a = 7.6628 (19) Å

  • b = 10.516 (3) Å

  • c = 29.855 (8) Å

  • V = 2405.9 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.06 mm−1

  • T = 123 K

  • 0.42 × 0.36 × 0.34 mm

Data collection

  • Rigaku AFC10/Saturn724+ diffractometer

  • 18847 measured reflections

  • 3143 independent reflections

  • 2973 reflections with I > 2σ(I)

  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038

  • wR(F 2) = 0.086

  • S = 1.00

  • 3143 reflections

  • 268 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052906/cv5014sup1.cif

e-67-0o244-sup1.cif (26.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052906/cv5014Isup2.hkl

e-67-0o244-Isup2.hkl (151.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This project was supported by the Educational Commission of Zhejiang Province (grant No. GD09071160185). The authors acknowledge Professor Kai-bei Yu, State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, for his help with the diffraction experiment.

supplementary crystallographic information

Comment

Many analogues of brassinolide as plant regulator have been isolated from a wide variety of plants, and there has been intense activity in synthesis of these brassinosteroids. We found the same phenomena that our immediates and products were synthesized with impurities by McMorris and Brosa's methods. Herewith we present the crystal structure of the title compound, (I).

In the title molecule, ring A shows an envelope conformation, and atoms C2, C3, C5 and C10 are coplanar with the r.m.s. deviation of 0.018 (1) Å. Atom C1 deviates 0.446 (3) Å from this mean plane, which make a dihedral angle of 68.20 (13) ° with the plane C3/C4/C5. Rings B and C have regular chair conformations, respectively; while ring D has an envelope conformation.

Experimental

(22E,24R)-3α,5-Cyclo-5α-ergosta-22-en-6-one was synthesized according to the known method (McMorris et al., 1993) as a powder. Crystals of (I) suitable for structure analysis were obtained by slow evaporation from a mixture of EtOAC and ethanol (volume proportion, 9:1) as colourless prisms.

Refinement

C-bound H atoms were placed at calculated positions (C—H 0.93–0.98 Å) and constrained to ride on their parent atoms, withUiso(Hmethyl) = 1.5Ueq(Cmethyl) or Uiso(Hnon-methyl) = 1.2Ueq(Cnon-methyl). Because of negligible anomalous scattering effects, 2359 Friedel pairs were averaged in the refinement. The absolute configuration has been assigned to correspond to the known chiral centres in a precursor molecule, which remained unchanged during the synthesis of (I).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I) shown with 30% probability displacement ellipsoids.

Crystal data

C28H44O Dx = 1.095 Mg m−3
Mr = 396.63 Melting point = 441–442 K
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 7977 reflections
a = 7.6628 (19) Å θ = 3.3–27.5°
b = 10.516 (3) Å µ = 0.06 mm−1
c = 29.855 (8) Å T = 123 K
V = 2405.9 (11) Å3 Block, colourless
Z = 4 0.42 × 0.36 × 0.34 mm
F(000) = 880
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Data collection

Rigaku AFC10/Saturn724+ diffractometer 2973 reflections with I > 2σ(I)
Radiation source: Rotating Anode Rint = 0.028
graphite θmax = 27.5°, θmin = 3.3°
Detector resolution: 28.5714 pixels mm-1 h = −9→8
phi and ω scans k = −12→13
18847 measured reflections l = −38→38
3143 independent reflections
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Refinement

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)] = 0.038 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086 H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0381P)2 + 0.526P] where P = (Fo2 + 2Fc2)/3
3143 reflections (Δ/σ)max < 0.001
268 parameters Δρmax = 0.25 e Å−3
0 restraints Δρmin = −0.13 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.30218 (17) 0.98106 (15) 0.72666 (5) 0.0450 (4)
C1 0.8956 (2) 1.11208 (17) 0.71079 (6) 0.0336 (4)
H1A 0.9464 1.1250 0.7409 0.040*
H1B 0.9918 1.1069 0.6887 0.040*
C2 0.7725 (3) 1.22209 (17) 0.69899 (7) 0.0386 (4)
H2A 0.8111 1.3020 0.7135 0.046*
H2B 0.7678 1.2353 0.6662 0.046*
C3 0.5968 (2) 1.18107 (18) 0.71677 (7) 0.0388 (4)
H3 0.4893 1.2217 0.7043 0.047*
C4 0.5881 (3) 1.1216 (2) 0.76191 (6) 0.0456 (5)
H4A 0.4750 1.1246 0.7779 0.055*
H4B 0.6920 1.1292 0.7814 0.055*
C5 0.6013 (2) 1.03587 (18) 0.72191 (6) 0.0318 (4)
C6 0.4414 (2) 0.96834 (18) 0.70745 (6) 0.0320 (4)
C7 0.4549 (2) 0.89255 (17) 0.66471 (5) 0.0282 (3)
H7A 0.4275 0.9492 0.6392 0.034*
H7B 0.3657 0.8245 0.6653 0.034*
C8 0.6335 (2) 0.83190 (15) 0.65663 (5) 0.0241 (3)
H8 0.6507 0.7629 0.6792 0.029*
C9 0.7817 (2) 0.92938 (15) 0.66207 (5) 0.0236 (3)
H9 0.7577 1.0002 0.6406 0.028*
C10 0.7850 (2) 0.98849 (17) 0.70976 (5) 0.0276 (3)
C11 0.9591 (2) 0.87132 (17) 0.64884 (6) 0.0275 (3)
H11A 1.0478 0.9397 0.6484 0.033*
H11B 0.9942 0.8092 0.6721 0.033*
C12 0.9587 (2) 0.80429 (16) 0.60302 (5) 0.0265 (3)
H12A 0.9410 0.8683 0.5791 0.032*
H12B 1.0735 0.7635 0.5981 0.032*
C13 0.8151 (2) 0.70341 (14) 0.59999 (5) 0.0235 (3)
C14 0.64205 (19) 0.77281 (15) 0.61000 (5) 0.0237 (3)
H14 0.6349 0.8450 0.5883 0.028*
C15 0.5007 (2) 0.67829 (17) 0.59621 (6) 0.0306 (4)
H15A 0.3908 0.7227 0.5885 0.037*
H15B 0.4772 0.6165 0.6205 0.037*
C16 0.5795 (2) 0.61158 (16) 0.55473 (6) 0.0296 (4)
H16A 0.5175 0.6385 0.5272 0.035*
H16B 0.5690 0.5181 0.5577 0.035*
C17 0.7754 (2) 0.65110 (15) 0.55229 (5) 0.0247 (3)
H17 0.7838 0.7243 0.5310 0.030*
C18 0.8492 (2) 0.59299 (16) 0.63263 (5) 0.0304 (4)
H18A 0.9635 0.5553 0.6262 0.046*
H18B 0.7582 0.5283 0.6290 0.046*
H18C 0.8476 0.6250 0.6635 0.046*
C19 0.8522 (2) 0.89395 (19) 0.74489 (5) 0.0372 (4)
H19A 0.8319 0.9284 0.7749 0.056*
H19B 0.9774 0.8801 0.7405 0.056*
H19C 0.7901 0.8130 0.7417 0.056*
C20 0.8887 (2) 0.54309 (15) 0.53322 (5) 0.0267 (3)
H20 0.8758 0.4675 0.5533 0.032*
C21 1.0830 (2) 0.57688 (17) 0.53063 (6) 0.0338 (4)
H21A 1.1455 0.5099 0.5144 0.051*
H21B 1.1306 0.5843 0.5610 0.051*
H21C 1.0972 0.6580 0.5149 0.051*
C22 0.8252 (2) 0.50642 (15) 0.48723 (5) 0.0286 (4)
H22 0.8351 0.5683 0.4642 0.034*
C23 0.7573 (2) 0.39577 (16) 0.47638 (5) 0.0285 (4)
H23 0.7463 0.3352 0.4998 0.034*
C24 0.6951 (2) 0.35497 (16) 0.43073 (5) 0.0287 (4)
H24 0.7161 0.4265 0.4093 0.034*
C25 0.7985 (3) 0.23792 (17) 0.41424 (6) 0.0355 (4)
H25 0.7812 0.1680 0.4365 0.043*
C26 0.7347 (3) 0.1902 (2) 0.36895 (7) 0.0510 (6)
H26A 0.7421 0.2592 0.3469 0.077*
H26B 0.6132 0.1620 0.3716 0.077*
H26C 0.8076 0.1189 0.3592 0.077*
C27 0.9935 (3) 0.2666 (2) 0.41187 (6) 0.0413 (5)
H27A 1.0139 0.3359 0.3905 0.062*
H27B 1.0563 0.1905 0.4020 0.062*
H27C 1.0354 0.2920 0.4416 0.062*
C28 0.4989 (3) 0.3298 (2) 0.43273 (6) 0.0406 (4)
H28A 0.4766 0.2547 0.4513 0.061*
H28B 0.4545 0.3148 0.4024 0.061*
H28C 0.4397 0.4036 0.4458 0.061*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0238 (7) 0.0577 (9) 0.0534 (8) 0.0054 (7) 0.0097 (6) −0.0095 (7)
C1 0.0242 (8) 0.0391 (9) 0.0375 (9) 0.0002 (8) −0.0065 (7) −0.0092 (8)
C2 0.0339 (10) 0.0321 (9) 0.0498 (11) 0.0007 (8) −0.0100 (8) −0.0125 (8)
C3 0.0303 (10) 0.0372 (9) 0.0489 (10) 0.0098 (8) −0.0078 (8) −0.0138 (8)
C4 0.0318 (10) 0.0638 (13) 0.0413 (10) 0.0091 (10) 0.0019 (8) −0.0193 (10)
C5 0.0226 (8) 0.0393 (9) 0.0335 (8) 0.0072 (8) −0.0004 (7) −0.0051 (7)
C6 0.0217 (8) 0.0359 (9) 0.0383 (9) 0.0072 (7) 0.0020 (7) 0.0040 (8)
C7 0.0171 (7) 0.0303 (8) 0.0373 (8) 0.0006 (7) 0.0002 (6) 0.0013 (7)
C8 0.0166 (7) 0.0251 (7) 0.0306 (8) 0.0016 (6) 0.0011 (6) 0.0038 (6)
C9 0.0171 (7) 0.0265 (7) 0.0271 (7) 0.0001 (6) −0.0015 (6) 0.0008 (6)
C10 0.0193 (8) 0.0349 (9) 0.0285 (8) 0.0040 (7) −0.0027 (6) −0.0018 (7)
C11 0.0150 (7) 0.0309 (8) 0.0366 (8) −0.0004 (6) −0.0016 (6) −0.0033 (7)
C12 0.0151 (7) 0.0285 (8) 0.0358 (8) −0.0011 (6) 0.0029 (6) −0.0034 (7)
C13 0.0187 (7) 0.0227 (7) 0.0289 (7) 0.0012 (6) −0.0004 (6) 0.0010 (6)
C14 0.0165 (7) 0.0238 (7) 0.0308 (8) −0.0008 (6) −0.0012 (6) 0.0035 (6)
C15 0.0196 (8) 0.0313 (9) 0.0408 (9) −0.0039 (7) −0.0005 (7) −0.0010 (7)
C16 0.0233 (8) 0.0276 (8) 0.0379 (8) −0.0037 (7) −0.0024 (7) 0.0004 (7)
C17 0.0215 (8) 0.0230 (7) 0.0295 (7) −0.0011 (6) −0.0010 (6) 0.0033 (6)
C18 0.0292 (8) 0.0286 (8) 0.0334 (8) 0.0050 (7) −0.0005 (7) 0.0036 (7)
C19 0.0304 (9) 0.0514 (11) 0.0299 (8) 0.0075 (9) −0.0035 (7) 0.0041 (8)
C20 0.0267 (8) 0.0235 (7) 0.0299 (8) 0.0007 (7) 0.0008 (6) 0.0018 (6)
C21 0.0271 (9) 0.0346 (9) 0.0397 (9) 0.0015 (8) 0.0027 (7) −0.0029 (8)
C22 0.0297 (9) 0.0265 (8) 0.0295 (8) 0.0018 (7) 0.0021 (7) 0.0038 (6)
C23 0.0300 (9) 0.0276 (8) 0.0280 (7) −0.0006 (7) 0.0009 (6) 0.0056 (7)
C24 0.0309 (9) 0.0266 (8) 0.0285 (8) −0.0059 (7) −0.0004 (7) 0.0052 (6)
C25 0.0479 (11) 0.0264 (8) 0.0324 (8) −0.0017 (8) 0.0036 (8) 0.0029 (7)
C26 0.0627 (15) 0.0449 (11) 0.0456 (11) −0.0063 (11) 0.0038 (10) −0.0136 (9)
C27 0.0436 (11) 0.0405 (10) 0.0397 (10) 0.0084 (9) 0.0043 (9) 0.0035 (9)
C28 0.0353 (10) 0.0442 (11) 0.0423 (10) −0.0095 (9) −0.0026 (8) 0.0002 (9)
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Geometric parameters (Å, °)

O1—C6 1.219 (2) C15—H15A 0.9900
C1—C2 1.533 (2) C15—H15B 0.9900
C1—C10 1.552 (2) C16—C17 1.559 (2)
C1—H1A 0.9900 C16—H16A 0.9900
C1—H1B 0.9900 C16—H16B 0.9900
C2—C3 1.511 (3) C17—C20 1.539 (2)
C2—H2A 0.9900 C17—H17 1.0000
C2—H2B 0.9900 C18—H18A 0.9800
C3—C4 1.487 (3) C18—H18B 0.9800
C3—C5 1.535 (3) C18—H18C 0.9800
C3—H3 1.0000 C19—H19A 0.9800
C4—C5 1.500 (2) C19—H19B 0.9800
C4—H4A 0.9900 C19—H19C 0.9800
C4—H4B 0.9900 C20—C22 1.507 (2)
C5—C6 1.481 (2) C20—C21 1.533 (2)
C5—C10 1.536 (2) C20—H20 1.0000
C6—C7 1.509 (2) C21—H21A 0.9800
C7—C8 1.528 (2) C21—H21B 0.9800
C7—H7A 0.9900 C21—H21C 0.9800
C7—H7B 0.9900 C22—C23 1.316 (2)
C8—C14 1.526 (2) C22—H22 0.9500
C8—C9 1.539 (2) C23—C24 1.507 (2)
C8—H8 1.0000 C23—H23 0.9500
C9—C11 1.542 (2) C24—C28 1.526 (3)
C9—C10 1.554 (2) C24—C25 1.546 (2)
C9—H9 1.0000 C24—H24 1.0000
C10—C19 1.534 (2) C25—C26 1.522 (2)
C11—C12 1.539 (2) C25—C27 1.525 (3)
C11—H11A 0.9900 C25—H25 1.0000
C11—H11B 0.9900 C26—H26A 0.9800
C12—C13 1.531 (2) C26—H26B 0.9800
C12—H12A 0.9900 C26—H26C 0.9800
C12—H12B 0.9900 C27—H27A 0.9800
C13—C18 1.538 (2) C27—H27B 0.9800
C13—C14 1.543 (2) C27—H27C 0.9800
C13—C17 1.558 (2) C28—H28A 0.9800
C14—C15 1.527 (2) C28—H28B 0.9800
C14—H14 1.0000 C28—H28C 0.9800
C15—C16 1.546 (2)
C2—C1—C10 106.93 (13) C13—C14—H14 106.3
C2—C1—H1A 110.3 C14—C15—C16 103.54 (13)
C10—C1—H1A 110.3 C14—C15—H15A 111.1
C2—C1—H1B 110.3 C16—C15—H15A 111.1
C10—C1—H1B 110.3 C14—C15—H15B 111.1
H1A—C1—H1B 108.6 C16—C15—H15B 111.1
C3—C2—C1 104.63 (15) H15A—C15—H15B 109.0
C3—C2—H2A 110.8 C15—C16—C17 107.05 (13)
C1—C2—H2A 110.8 C15—C16—H16A 110.3
C3—C2—H2B 110.8 C17—C16—H16A 110.3
C1—C2—H2B 110.8 C15—C16—H16B 110.3
H2A—C2—H2B 108.9 C17—C16—H16B 110.3
C4—C3—C2 118.56 (16) H16A—C16—H16B 108.6
C4—C3—C5 59.46 (13) C20—C17—C13 119.25 (13)
C2—C3—C5 107.35 (15) C20—C17—C16 111.34 (13)
C4—C3—H3 118.8 C13—C17—C16 103.83 (12)
C2—C3—H3 118.8 C20—C17—H17 107.3
C5—C3—H3 118.8 C13—C17—H17 107.3
C3—C4—C5 61.86 (12) C16—C17—H17 107.3
C3—C4—H4A 117.6 C13—C18—H18A 109.5
C5—C4—H4A 117.6 C13—C18—H18B 109.5
C3—C4—H4B 117.6 H18A—C18—H18B 109.5
C5—C4—H4B 117.6 C13—C18—H18C 109.5
H4A—C4—H4B 114.7 H18A—C18—H18C 109.5
C6—C5—C4 117.68 (15) H18B—C18—H18C 109.5
C6—C5—C3 115.35 (15) C10—C19—H19A 109.5
C4—C5—C3 58.68 (13) C10—C19—H19B 109.5
C6—C5—C10 122.22 (14) H19A—C19—H19B 109.5
C4—C5—C10 116.48 (14) C10—C19—H19C 109.5
C3—C5—C10 108.69 (15) H19A—C19—H19C 109.5
O1—C6—C5 122.30 (17) H19B—C19—H19C 109.5
O1—C6—C7 121.09 (16) C22—C20—C21 109.13 (14)
C5—C6—C7 116.34 (14) C22—C20—C17 110.07 (13)
C6—C7—C8 114.52 (13) C21—C20—C17 113.28 (13)
C6—C7—H7A 108.6 C22—C20—H20 108.1
C8—C7—H7A 108.6 C21—C20—H20 108.1
C6—C7—H7B 108.6 C17—C20—H20 108.1
C8—C7—H7B 108.6 C20—C21—H21A 109.5
H7A—C7—H7B 107.6 C20—C21—H21B 109.5
C14—C8—C7 110.61 (12) H21A—C21—H21B 109.5
C14—C8—C9 109.61 (12) C20—C21—H21C 109.5
C7—C8—C9 111.50 (13) H21A—C21—H21C 109.5
C14—C8—H8 108.3 H21B—C21—H21C 109.5
C7—C8—H8 108.3 C23—C22—C20 125.33 (14)
C9—C8—H8 108.3 C23—C22—H22 117.3
C8—C9—C11 111.11 (12) C20—C22—H22 117.3
C8—C9—C10 112.03 (12) C22—C23—C24 126.84 (14)
C11—C9—C10 112.28 (12) C22—C23—H23 116.6
C8—C9—H9 107.0 C24—C23—H23 116.6
C11—C9—H9 107.0 C23—C24—C28 109.02 (14)
C10—C9—H9 107.0 C23—C24—C25 110.59 (14)
C19—C10—C5 110.86 (14) C28—C24—C25 112.30 (15)
C19—C10—C1 110.24 (13) C23—C24—H24 108.3
C5—C10—C1 102.93 (13) C28—C24—H24 108.3
C19—C10—C9 111.87 (14) C25—C24—H24 108.3
C5—C10—C9 109.40 (12) C26—C25—C27 109.82 (16)
C1—C10—C9 111.20 (13) C26—C25—C24 112.33 (16)
C12—C11—C9 114.02 (13) C27—C25—C24 111.04 (15)
C12—C11—H11A 108.7 C26—C25—H25 107.8
C9—C11—H11A 108.7 C27—C25—H25 107.8
C12—C11—H11B 108.7 C24—C25—H25 107.8
C9—C11—H11B 108.7 C25—C26—H26A 109.5
H11A—C11—H11B 107.6 C25—C26—H26B 109.5
C13—C12—C11 111.80 (13) H26A—C26—H26B 109.5
C13—C12—H12A 109.3 C25—C26—H26C 109.5
C11—C12—H12A 109.3 H26A—C26—H26C 109.5
C13—C12—H12B 109.3 H26B—C26—H26C 109.5
C11—C12—H12B 109.3 C25—C27—H27A 109.5
H12A—C12—H12B 107.9 C25—C27—H27B 109.5
C12—C13—C18 111.35 (13) H27A—C27—H27B 109.5
C12—C13—C14 106.13 (12) C25—C27—H27C 109.5
C18—C13—C14 112.40 (12) H27A—C27—H27C 109.5
C12—C13—C17 116.03 (12) H27B—C27—H27C 109.5
C18—C13—C17 110.25 (12) C24—C28—H28A 109.5
C14—C13—C17 100.14 (12) C24—C28—H28B 109.5
C8—C14—C15 118.71 (13) H28A—C28—H28B 109.5
C8—C14—C13 113.96 (12) C24—C28—H28C 109.5
C15—C14—C13 104.43 (12) H28A—C28—H28C 109.5
C8—C14—H14 106.3 H28B—C28—H28C 109.5
C15—C14—H14 106.3
C10—C1—C2—C3 31.09 (18) C11—C9—C10—C1 70.92 (16)
C1—C2—C3—C4 43.3 (2) C8—C9—C11—C12 50.03 (18)
C1—C2—C3—C5 −20.85 (19) C10—C9—C11—C12 176.38 (13)
C2—C3—C4—C5 −94.19 (18) C9—C11—C12—C13 −54.27 (18)
C3—C4—C5—C6 −104.28 (18) C11—C12—C13—C18 −65.93 (17)
C3—C4—C5—C10 96.66 (18) C11—C12—C13—C14 56.69 (16)
C4—C3—C5—C6 108.27 (17) C11—C12—C13—C17 166.88 (13)
C2—C3—C5—C6 −138.33 (15) C7—C8—C14—C15 −53.32 (18)
C2—C3—C5—C4 113.41 (17) C9—C8—C14—C15 −176.67 (13)
C4—C3—C5—C10 −110.19 (16) C7—C8—C14—C13 −177.00 (13)
C2—C3—C5—C10 3.2 (2) C9—C8—C14—C13 59.65 (16)
C4—C5—C6—O1 0.4 (3) C12—C13—C14—C8 −61.60 (15)
C3—C5—C6—O1 −66.0 (2) C18—C13—C14—C8 60.35 (17)
C10—C5—C6—O1 158.13 (18) C17—C13—C14—C8 177.35 (12)
C4—C5—C6—C7 174.52 (15) C12—C13—C14—C15 167.31 (13)
C3—C5—C6—C7 108.16 (18) C18—C13—C14—C15 −70.75 (15)
C10—C5—C6—C7 −27.7 (2) C17—C13—C14—C15 46.26 (14)
O1—C6—C7—C8 −152.17 (17) C8—C14—C15—C16 −164.04 (13)
C5—C6—C7—C8 33.6 (2) C13—C14—C15—C16 −35.79 (15)
C6—C7—C8—C14 −172.34 (13) C14—C15—C16—C17 11.02 (16)
C6—C7—C8—C9 −50.10 (18) C12—C13—C17—C20 83.68 (17)
C14—C8—C9—C11 −50.93 (16) C18—C13—C17—C20 −44.06 (18)
C7—C8—C9—C11 −173.74 (13) C14—C13—C17—C20 −162.65 (13)
C14—C8—C9—C10 −177.42 (12) C12—C13—C17—C16 −151.75 (13)
C7—C8—C9—C10 59.77 (16) C18—C13—C17—C16 80.52 (15)
C6—C5—C10—C19 −88.33 (19) C14—C13—C17—C16 −38.08 (14)
C4—C5—C10—C19 69.7 (2) C15—C16—C17—C20 146.76 (13)
C3—C5—C10—C19 133.29 (16) C15—C16—C17—C13 17.23 (16)
C6—C5—C10—C1 153.80 (16) C13—C17—C20—C22 179.04 (13)
C4—C5—C10—C1 −48.18 (19) C16—C17—C20—C22 58.18 (17)
C3—C5—C10—C1 15.43 (17) C13—C17—C20—C21 −58.47 (18)
C6—C5—C10—C9 35.5 (2) C16—C17—C20—C21 −179.34 (13)
C4—C5—C10—C9 −166.48 (15) C21—C20—C22—C23 120.14 (18)
C3—C5—C10—C9 −102.87 (15) C17—C20—C22—C23 −114.96 (19)
C2—C1—C10—C19 −146.85 (15) C20—C22—C23—C24 −179.02 (15)
C2—C1—C10—C5 −28.55 (17) C22—C23—C24—C28 −116.44 (19)
C2—C1—C10—C9 88.48 (16) C22—C23—C24—C25 119.62 (19)
C8—C9—C10—C19 73.02 (17) C23—C24—C25—C26 177.68 (15)
C11—C9—C10—C19 −52.83 (18) C28—C24—C25—C26 55.6 (2)
C8—C9—C10—C5 −50.22 (17) C23—C24—C25—C27 −58.90 (18)
C11—C9—C10—C5 −176.07 (14) C28—C24—C25—C27 179.07 (15)
C8—C9—C10—C1 −163.23 (12)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5014).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052906/cv5014sup1.cif

e-67-0o244-sup1.cif (26.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052906/cv5014Isup2.hkl

e-67-0o244-Isup2.hkl (151.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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