24-Methyl­enecholest-4-ene-3β,6β-diol

The title compound, C₂₈H₄₆O₂, was isolated from soft coral (Nephthea sp.) collected from Yongxing island of the Xisha archipelago in the South China Sea and its crystal structure has been determined. In the crystal structure, inter­molecular O—H...O hydrogen-bond inter­actions link the mol­ecules into extended ribbons parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• R factor = 0.061
• wR factor = 0.215
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker,1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

24-Methylenecholest-4-ene-3β,6β-diol

Crystal data

C28H46O2	Dx = 1.084 Mg m^−3
Mr = 414.65	Melting point: 300° not melting K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 8.168 (3) Å	Cell parameters from 25 reflections
b = 10.933 (3) Å	θ = 12–18°
c = 28.446 (8) Å	µ = 0.07 mm^−1
V = 2540.2 (13) Å^3	T = 273 K
Z = 4	Block, colourless
F(000) = 920	0.50 × 0.40 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	3170 independent reflections
Radiation source: fine-focus sealed tube	2044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.97, Tmax = 0.99	k = −11→13
14474 measured reflections	l = −35→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.215	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1393P)^2 + 0.1882P] where P = (Fo^2 + 2Fc^2)/3
3170 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.5565 (3)	0.8068 (4)	0.97094 (9)	0.0800 (11)
H1	1.6509	0.7826	0.9677	0.120*
O2	0.8942 (3)	0.7746 (3)	0.95040 (9)	0.0719 (9)
H2	0.9372	0.7569	0.9755	0.108*
C1	1.4696 (4)	0.7918 (5)	0.92761 (13)	0.0620 (11)
H1A	1.5225	0.8421	0.9035	0.074*
C2	1.2989 (4)	0.8376 (4)	0.93480 (13)	0.0550 (10)
H2A	1.2845	0.9043	0.9547	0.066*
C3	1.1672 (4)	0.7905 (4)	0.91505 (12)	0.0502 (9)
C4	1.0028 (4)	0.8510 (4)	0.92374 (12)	0.0560 (10)
H4	1.0205	0.9274	0.9410	0.067*
C5	0.9177 (4)	0.8799 (4)	0.87768 (12)	0.0503 (9)
H5A	0.9757	0.9461	0.8622	0.060*
H5B	0.8075	0.9081	0.8843	0.060*
C6	0.9085 (4)	0.7714 (3)	0.84439 (12)	0.0443 (8)
H6	0.8411	0.7076	0.8590	0.053*
C7	0.8333 (4)	0.8054 (3)	0.79756 (11)	0.0437 (7)
H7	0.9092	0.8633	0.7828	0.052*
C8	0.6669 (5)	0.8670 (4)	0.79744 (13)	0.0557 (9)
H8A	0.6770	0.9534	0.8048	0.067*
H8B	0.5945	0.8292	0.8202	0.067*
C9	0.6021 (5)	0.8487 (4)	0.74717 (14)	0.0602 (10)
H9A	0.5974	0.9264	0.7308	0.072*
H9B	0.4929	0.8139	0.7479	0.072*
C10	0.7213 (5)	0.7608 (4)	0.72191 (13)	0.0539 (9)
H10	0.8007	0.8116	0.7050	0.065*
C11	0.8147 (4)	0.6984 (3)	0.76289 (12)	0.0480 (8)
C12	0.9892 (6)	0.6535 (4)	0.75278 (16)	0.0656 (11)
H12A	1.0497	0.7175	0.7368	0.079*
H12B	0.9844	0.5831	0.7321	0.079*
C13	1.0793 (5)	0.6183 (4)	0.79820 (16)	0.0696 (12)
H13A	1.0275	0.5463	0.8114	0.083*
H13B	1.1913	0.5968	0.7904	0.083*
C14	1.0815 (4)	0.7191 (4)	0.83541 (12)	0.0484 (8)
H14	1.1459	0.7862	0.8220	0.058*
C15	1.1707 (4)	0.6810 (4)	0.88158 (13)	0.0513 (9)
C16	1.3505 (4)	0.6518 (5)	0.86929 (16)	0.0689 (12)
H16A	1.3567	0.5692	0.8570	0.083*
H16B	1.3867	0.7071	0.8447	0.083*
C17	1.4663 (5)	0.6630 (5)	0.91113 (17)	0.0788 (15)
H17A	1.4296	0.6100	0.9364	0.095*
H17B	1.5756	0.6377	0.9020	0.095*
C18	1.0947 (6)	0.5695 (4)	0.90472 (18)	0.0760 (13)
H18A	1.0976	0.5018	0.8833	0.114*
H18B	0.9831	0.5871	0.9130	0.114*
H18C	1.1552	0.5492	0.9326	0.114*
C19	0.7087 (6)	0.5949 (4)	0.78374 (16)	0.0673 (12)
H19A	0.6997	0.5295	0.7613	0.101*
H19B	0.6015	0.6259	0.7908	0.101*
H19C	0.7588	0.5649	0.8120	0.101*
C20	0.6328 (6)	0.6826 (4)	0.68519 (15)	0.0699 (12)
H20	0.5505	0.6350	0.7023	0.084*
C21	0.7465 (8)	0.5899 (6)	0.6620 (2)	0.110 (2)
H21A	0.7999	0.5421	0.6858	0.165*
H21B	0.8272	0.6323	0.6436	0.165*
H21C	0.6839	0.5370	0.6419	0.165*
C22	0.5404 (8)	0.7584 (5)	0.64993 (16)	0.0860 (15)
H22A	0.6175	0.7912	0.6272	0.103*
H22B	0.4902	0.8270	0.6661	0.103*
C23	0.4091 (11)	0.6886 (7)	0.6240 (3)	0.150 (4)
H23A	0.4619	0.6252	0.6055	0.180*
H23B	0.3405	0.6481	0.6470	0.180*
C24	0.3032 (11)	0.7590 (7)	0.5926 (2)	0.115 (2)
C25	0.1574 (17)	0.7984 (14)	0.6069 (5)	0.270 (9)
H25A	0.0818	0.8269	0.5850	0.324*
H25B	0.1311	0.7974	0.6387	0.324*
C26	0.3039 (16)	0.8627 (9)	0.5156 (3)	0.189 (5)
H26A	0.3476	0.8531	0.4845	0.283*
H26B	0.3459	0.9365	0.5293	0.283*
H26C	0.1866	0.8672	0.5140	0.283*
C27	0.3520 (13)	0.7577 (8)	0.5446 (3)	0.142 (3)
H27	0.4719	0.7552	0.5444	0.170*
C28	0.2923 (17)	0.6351 (8)	0.5224 (3)	0.186 (5)
H28A	0.3259	0.5680	0.5419	0.279*
H28B	0.3393	0.6259	0.4917	0.279*
H28C	0.1751	0.6358	0.5200	0.279*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0289 (12)	0.160 (3)	0.0515 (14)	−0.0017 (17)	−0.0040 (11)	0.0139 (19)
O2	0.0268 (11)	0.137 (3)	0.0517 (14)	0.0011 (15)	0.0044 (11)	0.0159 (17)
C1	0.0289 (16)	0.106 (3)	0.0512 (19)	−0.003 (2)	0.0004 (15)	0.012 (2)
C2	0.0303 (16)	0.085 (3)	0.0503 (18)	−0.0027 (17)	−0.0004 (15)	0.0089 (19)
C3	0.0286 (15)	0.075 (2)	0.0474 (17)	0.0015 (17)	0.0019 (13)	0.0066 (18)
C4	0.0330 (17)	0.085 (3)	0.0495 (19)	0.0031 (18)	0.0022 (15)	−0.0055 (19)
C5	0.0313 (16)	0.066 (2)	0.0537 (19)	0.0050 (16)	−0.0029 (15)	−0.0044 (17)
C6	0.0326 (15)	0.0503 (18)	0.0499 (17)	0.0002 (15)	−0.0001 (13)	0.0017 (15)
C7	0.0413 (17)	0.0442 (17)	0.0457 (16)	−0.0016 (15)	0.0014 (14)	−0.0017 (15)
C8	0.052 (2)	0.058 (2)	0.057 (2)	0.0120 (19)	−0.0036 (17)	−0.0075 (18)
C9	0.056 (2)	0.060 (2)	0.064 (2)	0.0105 (19)	−0.0102 (19)	−0.0076 (19)
C10	0.053 (2)	0.054 (2)	0.0549 (19)	0.0006 (17)	−0.0070 (17)	−0.0072 (17)
C11	0.0447 (18)	0.0470 (19)	0.0524 (19)	0.0010 (16)	−0.0021 (15)	−0.0073 (16)
C12	0.056 (2)	0.073 (3)	0.068 (2)	0.014 (2)	−0.0057 (19)	−0.022 (2)
C13	0.050 (2)	0.075 (3)	0.083 (3)	0.022 (2)	−0.008 (2)	−0.020 (2)
C14	0.0344 (16)	0.056 (2)	0.0553 (19)	0.0021 (16)	0.0023 (14)	0.0011 (17)
C15	0.0295 (15)	0.064 (2)	0.061 (2)	0.0057 (16)	0.0011 (15)	0.0068 (18)
C16	0.0351 (19)	0.091 (3)	0.080 (3)	0.015 (2)	0.0027 (19)	−0.003 (2)
C17	0.0334 (18)	0.121 (4)	0.082 (3)	0.023 (2)	−0.0049 (19)	0.017 (3)
C18	0.066 (3)	0.071 (3)	0.091 (3)	0.000 (2)	−0.006 (3)	0.024 (2)
C19	0.068 (3)	0.052 (2)	0.082 (3)	−0.011 (2)	−0.012 (2)	0.002 (2)
C20	0.070 (3)	0.070 (3)	0.069 (2)	0.010 (2)	−0.016 (2)	−0.018 (2)
C21	0.121 (5)	0.115 (4)	0.095 (4)	0.032 (4)	−0.028 (4)	−0.059 (3)
C22	0.112 (4)	0.087 (3)	0.059 (2)	0.007 (3)	−0.023 (3)	−0.003 (2)
C23	0.182 (8)	0.110 (5)	0.158 (6)	0.021 (5)	−0.116 (6)	−0.011 (5)
C24	0.138 (6)	0.116 (5)	0.090 (4)	0.029 (5)	−0.044 (4)	−0.007 (4)
C25	0.250 (16)	0.333 (19)	0.227 (13)	0.183 (16)	0.007 (12)	−0.051 (14)
C26	0.210 (10)	0.192 (10)	0.165 (7)	−0.045 (9)	−0.064 (8)	0.081 (8)
C27	0.171 (8)	0.138 (6)	0.116 (5)	0.004 (6)	−0.014 (6)	0.025 (5)
C28	0.280 (14)	0.149 (8)	0.129 (6)	0.012 (10)	−0.042 (8)	−0.051 (6)

Geometric parameters (Å, º)

O1—C1	1.432 (4)	C14—H14	0.9800
O1—H1	0.8200	C15—C18	1.518 (6)
O2—C4	1.435 (5)	C15—C16	1.543 (5)
O2—H2	0.8200	C16—C17	1.525 (6)
C1—C17	1.485 (7)	C16—H16A	0.9700
C1—C2	1.496 (5)	C16—H16B	0.9700
C1—H1A	0.9800	C17—H17A	0.9700
C2—C3	1.318 (5)	C17—H17B	0.9700
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.517 (5)	C18—H18B	0.9600
C3—C15	1.530 (6)	C18—H18C	0.9600
C4—C5	1.517 (5)	C19—H19A	0.9600
C4—H4	0.9800	C19—H19B	0.9600
C5—C6	1.520 (5)	C19—H19C	0.9600
C5—H5A	0.9700	C20—C22	1.504 (6)
C5—H5B	0.9700	C20—C21	1.524 (7)
C6—C7	1.513 (5)	C20—H20	0.9800
C6—C14	1.546 (5)	C21—H21A	0.9600
C6—H6	0.9800	C21—H21B	0.9600
C7—C8	1.517 (5)	C21—H21C	0.9600
C7—C11	1.538 (5)	C22—C23	1.510 (8)
C7—H7	0.9800	C22—H22A	0.9700
C8—C9	1.538 (5)	C22—H22B	0.9700
C8—H8A	0.9700	C23—C24	1.461 (9)
C8—H8B	0.9700	C23—H23A	0.9700
C9—C10	1.545 (6)	C23—H23B	0.9700
C9—H9A	0.9700	C24—C25	1.329 (13)
C9—H9B	0.9700	C24—C27	1.423 (10)
C10—C20	1.531 (5)	C25—H25A	0.9300
C10—C11	1.551 (5)	C25—H25B	0.9300
C10—H10	0.9800	C26—C27	1.467 (11)
C11—C12	1.535 (6)	C26—H26A	0.9600
C11—C19	1.543 (6)	C26—H26B	0.9600
C12—C13	1.536 (6)	C26—H26C	0.9600
C12—H12A	0.9700	C27—C28	1.560 (12)
C12—H12B	0.9700	C27—H27	0.9800
C13—C14	1.528 (6)	C28—H28A	0.9600
C13—H13A	0.9700	C28—H28B	0.9600
C13—H13B	0.9700	C28—H28C	0.9600
C14—C15	1.558 (5)
C1—O1—H1	109.5	C15—C14—H14	106.1
C4—O2—H2	109.5	C18—C15—C3	110.5 (3)
O1—C1—C17	112.9 (4)	C18—C15—C16	108.7 (4)
O1—C1—C2	107.8 (3)	C3—C15—C16	108.7 (3)
C17—C1—C2	110.1 (4)	C18—C15—C14	112.9 (3)
O1—C1—H1A	108.6	C3—C15—C14	107.9 (3)
C17—C1—H1A	108.6	C16—C15—C14	108.0 (3)
C2—C1—H1A	108.6	C17—C16—C15	113.4 (4)
C3—C2—C1	124.8 (4)	C17—C16—H16A	108.9
C3—C2—H2A	117.6	C15—C16—H16A	108.9
C1—C2—H2A	117.6	C17—C16—H16B	108.9
C2—C3—C4	118.8 (3)	C15—C16—H16B	108.9
C2—C3—C15	123.8 (3)	H16A—C16—H16B	107.7
C4—C3—C15	117.3 (3)	C1—C17—C16	109.5 (4)
O2—C4—C5	107.1 (3)	C1—C17—H17A	109.8
O2—C4—C3	112.3 (3)	C16—C17—H17A	109.8
C5—C4—C3	110.8 (3)	C1—C17—H17B	109.8
O2—C4—H4	108.8	C16—C17—H17B	109.8
C5—C4—H4	108.8	H17A—C17—H17B	108.2
C3—C4—H4	108.8	C15—C18—H18A	109.5
C4—C5—C6	113.5 (3)	C15—C18—H18B	109.5
C4—C5—H5A	108.9	H18A—C18—H18B	109.5
C6—C5—H5A	108.9	C15—C18—H18C	109.5
C4—C5—H5B	108.9	H18A—C18—H18C	109.5
C6—C5—H5B	108.9	H18B—C18—H18C	109.5
H5A—C5—H5B	107.7	C11—C19—H19A	109.5
C7—C6—C5	112.1 (3)	C11—C19—H19B	109.5
C7—C6—C14	108.4 (3)	H19A—C19—H19B	109.5
C5—C6—C14	110.3 (3)	C11—C19—H19C	109.5
C7—C6—H6	108.6	H19A—C19—H19C	109.5
C5—C6—H6	108.6	H19B—C19—H19C	109.5
C14—C6—H6	108.6	C22—C20—C21	112.5 (4)
C6—C7—C8	118.3 (3)	C22—C20—C10	112.6 (4)
C6—C7—C11	114.7 (3)	C21—C20—C10	112.3 (4)
C8—C7—C11	104.3 (3)	C22—C20—H20	106.3
C6—C7—H7	106.2	C21—C20—H20	106.3
C8—C7—H7	106.2	C10—C20—H20	106.3
C11—C7—H7	106.2	C20—C21—H21A	109.5
C7—C8—C9	104.6 (3)	C20—C21—H21B	109.5
C7—C8—H8A	110.8	H21A—C21—H21B	109.5
C9—C8—H8A	110.8	C20—C21—H21C	109.5
C7—C8—H8B	110.8	H21A—C21—H21C	109.5
C9—C8—H8B	110.8	H21B—C21—H21C	109.5
H8A—C8—H8B	108.9	C20—C22—C23	113.8 (5)
C8—C9—C10	107.3 (3)	C20—C22—H22A	108.8
C8—C9—H9A	110.3	C23—C22—H22A	108.8
C10—C9—H9A	110.3	C20—C22—H22B	108.8
C8—C9—H9B	110.3	C23—C22—H22B	108.8
C10—C9—H9B	110.3	H22A—C22—H22B	107.7
H9A—C9—H9B	108.5	C24—C23—C22	116.9 (6)
C20—C10—C9	111.5 (3)	C24—C23—H23A	108.1
C20—C10—C11	119.9 (3)	C22—C23—H23A	108.1
C9—C10—C11	103.5 (3)	C24—C23—H23B	108.1
C20—C10—H10	107.1	C22—C23—H23B	108.1
C9—C10—H10	107.1	H23A—C23—H23B	107.3
C11—C10—H10	107.1	C25—C24—C27	123.1 (9)
C12—C11—C7	105.7 (3)	C25—C24—C23	121.0 (10)
C12—C11—C19	111.0 (4)	C27—C24—C23	114.5 (8)
C7—C11—C19	111.5 (3)	C24—C25—H25A	120.0
C12—C11—C10	117.2 (3)	C24—C25—H25B	120.0
C7—C11—C10	101.3 (3)	H25A—C25—H25B	120.0
C19—C11—C10	109.6 (3)	C27—C26—H26A	109.5
C11—C12—C13	111.6 (3)	C27—C26—H26B	109.5
C11—C12—H12A	109.3	H26A—C26—H26B	109.5
C13—C12—H12A	109.3	C27—C26—H26C	109.5
C11—C12—H12B	109.3	H26A—C26—H26C	109.5
C13—C12—H12B	109.3	H26B—C26—H26C	109.5
H12A—C12—H12B	108.0	C24—C27—C26	117.2 (9)
C14—C13—C12	114.1 (3)	C24—C27—C28	108.0 (8)
C14—C13—H13A	108.7	C26—C27—C28	111.2 (7)
C12—C13—H13A	108.7	C24—C27—H27	106.6
C14—C13—H13B	108.7	C26—C27—H27	106.6
C12—C13—H13B	108.7	C28—C27—H27	106.6
H13A—C13—H13B	107.6	C27—C28—H28A	109.5
C13—C14—C6	111.7 (3)	C27—C28—H28B	109.5
C13—C14—C15	113.4 (3)	H28A—C28—H28B	109.5
C6—C14—C15	112.8 (3)	C27—C28—H28C	109.5
C13—C14—H14	106.1	H28A—C28—H28C	109.5
C6—C14—H14	106.1	H28B—C28—H28C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.05	2.841 (4)	162
O2—H2···O1^ii	0.82	1.94	2.749 (4)	170

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, −z+2.