(22E,24R)-5α-Ergosta-2,22-dien-6-one

Sheng, L.; Zeng, F.; Chen, F.; Xia, C.

doi:10.1107/S1600536811002388

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o507

doi:10.1107/S1600536811002388

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(22E,24R)-5α-Ergosta-2,22-dien-6-one

Liu-qing Sheng,^a ^* Fang Zeng,^b Fei Chen ^a and Chun-nian Xia ^b

^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

(Received 24 December 2010; accepted 17 January 2011; online 29 January 2011)

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 envelope conformation. In the crystal, weak intermolecular C—H⋯O interactions link molecules into chains along the b axis. The absolute configuration 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 crystal structure of the related compound (22E,24R)-3α,5-cyclo-5α-ergosta-22-en-6-one, see: Sheng et al. (2011 ).

Experimental

Crystal data

C₂₈H₄₄O
M_r = 396.63
Monoclinic, P 2₁
a = 9.812 (3) Å
b = 7.578 (2) Å
c = 16.130 (5) Å
β = 92.832 (4)°
V = 1197.8 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 123 K
0.58 × 0.34 × 0.33 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
10906 measured reflections
2908 independent reflections
2598 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.091
S = 1.03
2908 reflections
268 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

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: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002388/cv5027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002388/cv5027Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For details of the synthesis, see: McMorris et al. (1993). For the crystal structure of the related compound (22E,24R)-3α,5-cyclo-5α-ergosta-22-en-6-one, see: Sheng et al. (2011).

Experimental top

(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.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: 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).

Figures top

Fig. 1. The molecular structure of (I) shown with 30% probability displacement ellipsoids.

(22E,24R)-5α-Ergosta-2,22-dien-6-one top

Crystal data top

C₂₈H₄₄O	F(000) = 440
M_r = 396.63	D_x = 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

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2598 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.030
Graphite monochromator	θ_max = 27.5°, θ_min = 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 top

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(F_o²) + (0.0346P)² + 0.296P] where P = (F_o² + 2F_c²)/3
2908 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₈H₄₄O	V = 1197.8 (6) Å³
M_r = 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)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2598 reflections with I > 2σ(I)
10906 measured reflections	R_int = 0.030
2908 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
2908 reflections	Δρ_min = −0.14 e Å⁻³
268 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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