(20S)-22-Acetoxymethyl-6β-meth­oxy-3α,5-dihydro-3′H-cyclo­propa[3α,5]-5α-pregnane

Ketuly, K.A.; Hadi, A.H.A.; Ng, S.W.

doi:10.1107/S1600536809020674

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1486

doi:10.1107/S1600536809020674

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(20S)-22-Acetoxymethyl-6β-methoxy-3α,5-dihydro-3′H-cyclopropa[3α,5]-5α-pregnane

Kamal Aziz Ketuly,^a A. Hamid A. Hadi ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 May 2009; accepted 31 May 2009; online 6 June 2009)

In the title steroid derivative, C₂₅H₄₀O₃, the fused cyclopropane unit that corresponds to a part of the A ring has a β-configuration and the associated cyclopentane ring an envelope-shaped conformation.

Related literature

For the synthesis and crystal structure of the iodo-substituted compound, see: Ketuly et al. (2009 ). The absolute configuration of the acetoxymethyl title compound is that of the iodo-substituted compound.

Experimental

Crystal data

C₂₅H₄₀O₃
M_r = 388.57
Monoclinic, P 2₁
a = 9.8222 (1) Å
b = 7.6128 (1) Å
c = 15.2309 (2) Å
β = 107.604 (1)°
V = 1085.55 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
10411 measured reflections
2674 independent reflections
2550 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.05
2674 reflections
258 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020674/xu2534sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020674/xu2534Isup2.hkl

checkCIF report

Related literature top

For the synthesis and crystal structure of the iodo-substituted steroid, see: Ketuly et al. (2009).

Experimental top

(20S)-22-Iodomethyl-6-methoxy-3,5-dihydro-3'H-cyclopropa[3α,5]-5-pregnane (Ketuly et al., 2009) (250 mg) was dissolved in pyridine (2 ml) and acetic anhydride (2 ml). The solution was heated at 353 K for an hour. The solvent was evaporated to give a product (280 mg), which was purified by recrystallization from ethanol (140 mg); m.p. 395–396 K. Mass spectrum: M⁺ 338. C&H elemental analysis: calc. C 77.27, H 10.38% (found: C 77.06, H 10.44%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₅H₄₀O₃ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(20S)-22-Acetoxymethyl-6β-methoxy-3α,5-dihydro-3'H-cyclopropa[3α,5]-5α-pregnane top

Crystal data top

C₂₅H₄₀O₃	F(000) = 428
M_r = 388.57	D_x = 1.189 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5999 reflections
a = 9.8222 (1) Å	θ = 2.2–28.3°
b = 7.6128 (1) Å	µ = 0.08 mm⁻¹
c = 15.2309 (2) Å	T = 100 K
β = 107.604 (1)°	Plate, colorless
V = 1085.55 (2) Å³	0.30 × 0.10 × 0.02 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2550 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −12→12
10411 measured reflections	k = −9→9
2674 independent reflections	l = −19→19

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0668P)² + 0.103P] where P = (F_o² + 2F_c²)/3
2674 reflections	(Δ/σ)_max = 0.001
258 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₄₀O₃	V = 1085.55 (2) Å³
M_r = 388.57	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.8222 (1) Å	µ = 0.08 mm⁻¹
b = 7.6128 (1) Å	T = 100 K
c = 15.2309 (2) Å	0.30 × 0.10 × 0.02 mm
β = 107.604 (1)°

Data collection top

Bruker SMART APEX diffractometer	2550 reflections with I > 2σ(I)
10411 measured reflections	R_int = 0.023
2674 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
2674 reflections	Δρ_min = −0.18 e Å⁻³
258 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.10395 (12)	0.50018 (19)	0.12290 (8)	0.0237 (3)
O2	0.24166 (13)	0.5963 (2)	0.03933 (8)	0.0286 (3)
O3	0.25451 (12)	0.95997 (17)	0.77203 (8)	0.0214 (3)
C1	0.49210 (17)	0.7214 (2)	0.92678 (10)	0.0213 (3)
H1C	0.5064	0.8353	0.9597	0.026*
H1D	0.4618	0.6239	0.9596	0.026*
C2	0.58913 (18)	0.6782 (2)	0.87028 (11)	0.0206 (3)
H2	0.6654	0.7638	0.8683	0.025*
C3	0.6102 (2)	0.4859 (3)	0.85413 (12)	0.0307 (4)
H3C	0.6701	0.4288	0.9112	0.037*
H3D	0.6561	0.4701	0.8050	0.037*
C4	0.4587 (2)	0.4096 (2)	0.82473 (12)	0.0308 (4)
H4C	0.4323	0.3696	0.8793	0.037*
H4D	0.4524	0.3084	0.7829	0.037*
C5	0.35775 (17)	0.5589 (2)	0.77468 (10)	0.0193 (3)
C6	0.2085 (2)	0.5381 (3)	0.78560 (12)	0.0312 (4)
H6D	0.2140	0.5544	0.8504	0.047*
H6E	0.1719	0.4203	0.7655	0.047*
H6F	0.1443	0.6263	0.7479	0.047*
C7	0.43341 (16)	0.7250 (2)	0.82255 (10)	0.0158 (3)
C8	0.39518 (15)	0.9004 (2)	0.77576 (10)	0.0153 (3)
H8	0.4669	0.9897	0.8092	0.018*
C9	0.23898 (18)	0.9981 (3)	0.86009 (12)	0.0258 (4)
H9D	0.1484	1.0596	0.8522	0.039*
H9E	0.3183	1.0726	0.8949	0.039*
H9F	0.2395	0.8882	0.8937	0.039*
C10	0.39576 (16)	0.8908 (2)	0.67622 (10)	0.0158 (3)
H10C	0.4951	0.8746	0.6749	0.019*
H10D	0.3600	1.0032	0.6451	0.019*
C11	0.30351 (15)	0.7405 (2)	0.62360 (10)	0.0133 (3)
H11	0.2021	0.7609	0.6217	0.016*
C12	0.35449 (16)	0.5638 (2)	0.67192 (10)	0.0163 (3)
H12	0.4553	0.5475	0.6715	0.020*
C13	0.2681 (2)	0.4112 (2)	0.61596 (12)	0.0254 (4)
H13C	0.1674	0.4218	0.6155	0.030*
H13D	0.3059	0.2990	0.6466	0.030*
C14	0.27319 (19)	0.4064 (2)	0.51608 (11)	0.0221 (3)
H14C	0.3725	0.3848	0.5159	0.027*
H14D	0.2129	0.3087	0.4827	0.027*
C15	0.21989 (15)	0.5799 (2)	0.46676 (10)	0.0149 (3)
C16	0.05902 (15)	0.6053 (3)	0.45320 (11)	0.0224 (3)
H16D	0.0426	0.6124	0.5135	0.034*
H16E	0.0058	0.5056	0.4186	0.034*
H16F	0.0264	0.7141	0.4189	0.034*
C17	0.31116 (15)	0.7284 (2)	0.52507 (10)	0.0136 (3)
H17	0.4127	0.6996	0.5304	0.016*
C18	0.27348 (18)	0.8908 (2)	0.46325 (11)	0.0190 (3)
H18E	0.3526	0.9771	0.4791	0.023*
H18F	0.1857	0.9479	0.4685	0.023*
C19	0.24985 (18)	0.8151 (2)	0.36523 (10)	0.0212 (3)
H19C	0.3268	0.8547	0.3403	0.025*
H19D	0.1571	0.8552	0.3233	0.025*
C20	0.25155 (15)	0.6111 (2)	0.37410 (10)	0.0155 (3)
H20	0.3516	0.5709	0.3823	0.019*
C21	0.15462 (16)	0.5210 (2)	0.28707 (10)	0.0188 (3)
H21	0.0546	0.5633	0.2767	0.023*
C22	0.1550 (2)	0.3196 (3)	0.29402 (12)	0.0285 (4)
H22A	0.1066	0.2695	0.2333	0.043*
H22B	0.1050	0.2838	0.3379	0.043*
H22C	0.2538	0.2772	0.3153	0.043*
C23	0.20266 (16)	0.5758 (2)	0.20495 (10)	0.0202 (3)
H23D	0.2026	0.7054	0.1999	0.024*
H23E	0.3007	0.5328	0.2126	0.024*
C24	0.13665 (17)	0.5221 (2)	0.04415 (11)	0.0211 (3)
C25	0.0256 (2)	0.4403 (4)	−0.03584 (12)	0.0402 (5)
H25D	−0.0046	0.5256	−0.0862	0.060*
H25E	−0.0570	0.4052	−0.0165	0.060*
H25F	0.0659	0.3367	−0.0570	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0205 (5)	0.0370 (7)	0.0136 (5)	−0.0064 (5)	0.0052 (4)	−0.0046 (5)
O2	0.0325 (6)	0.0348 (7)	0.0209 (6)	−0.0102 (6)	0.0118 (5)	−0.0031 (6)
O3	0.0187 (5)	0.0283 (6)	0.0156 (5)	0.0068 (5)	0.0027 (4)	−0.0055 (5)
C1	0.0284 (8)	0.0204 (8)	0.0125 (7)	0.0008 (7)	0.0024 (6)	0.0001 (6)
C2	0.0216 (8)	0.0210 (8)	0.0158 (7)	0.0040 (6)	0.0008 (6)	0.0002 (6)
C3	0.0431 (11)	0.0242 (9)	0.0185 (8)	0.0145 (8)	0.0001 (7)	0.0013 (7)
C4	0.0559 (12)	0.0158 (8)	0.0159 (8)	0.0000 (9)	0.0034 (7)	0.0025 (7)
C5	0.0296 (8)	0.0149 (7)	0.0123 (7)	−0.0046 (7)	0.0046 (5)	0.0008 (6)
C6	0.0381 (10)	0.0397 (11)	0.0187 (8)	−0.0207 (9)	0.0129 (7)	−0.0035 (8)
C7	0.0185 (7)	0.0160 (7)	0.0123 (7)	0.0002 (6)	0.0037 (5)	−0.0004 (6)
C8	0.0151 (6)	0.0144 (7)	0.0157 (7)	0.0010 (6)	0.0038 (5)	−0.0010 (6)
C9	0.0210 (7)	0.0358 (10)	0.0205 (8)	0.0039 (7)	0.0063 (6)	−0.0081 (7)
C10	0.0202 (7)	0.0124 (7)	0.0152 (7)	−0.0004 (6)	0.0059 (5)	0.0006 (6)
C11	0.0148 (6)	0.0127 (7)	0.0126 (6)	0.0004 (5)	0.0045 (5)	0.0000 (5)
C12	0.0230 (7)	0.0125 (7)	0.0123 (7)	−0.0016 (6)	0.0039 (5)	0.0008 (6)
C13	0.0446 (10)	0.0127 (7)	0.0162 (8)	−0.0077 (7)	0.0053 (7)	0.0005 (6)
C14	0.0337 (9)	0.0132 (7)	0.0169 (8)	−0.0010 (7)	0.0039 (6)	−0.0014 (6)
C15	0.0177 (7)	0.0150 (7)	0.0128 (6)	−0.0004 (6)	0.0061 (5)	−0.0010 (6)
C16	0.0165 (7)	0.0333 (9)	0.0187 (7)	−0.0039 (7)	0.0071 (5)	−0.0034 (7)
C17	0.0151 (6)	0.0130 (6)	0.0129 (7)	0.0003 (6)	0.0046 (5)	0.0003 (6)
C18	0.0274 (8)	0.0150 (7)	0.0144 (7)	−0.0007 (6)	0.0060 (6)	0.0012 (6)
C19	0.0307 (8)	0.0195 (8)	0.0131 (7)	−0.0020 (7)	0.0064 (6)	0.0019 (6)
C20	0.0154 (6)	0.0182 (7)	0.0132 (7)	−0.0009 (6)	0.0050 (5)	−0.0014 (6)
C21	0.0183 (7)	0.0250 (8)	0.0133 (7)	−0.0040 (6)	0.0049 (6)	−0.0035 (6)
C22	0.0410 (10)	0.0262 (9)	0.0179 (8)	−0.0116 (8)	0.0085 (7)	−0.0057 (7)
C23	0.0201 (7)	0.0265 (8)	0.0134 (7)	−0.0044 (7)	0.0039 (5)	−0.0033 (6)
C24	0.0239 (7)	0.0236 (8)	0.0167 (7)	−0.0010 (6)	0.0076 (6)	−0.0023 (6)
C25	0.0399 (10)	0.0626 (15)	0.0185 (9)	−0.0212 (11)	0.0092 (7)	−0.0084 (9)

Geometric parameters (Å, º) top

O1—C24	1.3425 (19)	C12—C13	1.536 (2)
O1—C23	1.4491 (18)	C12—H12	1.0000
O2—C24	1.198 (2)	C13—C14	1.538 (2)
O3—C9	1.4247 (19)	C13—H13C	0.9900
O3—C8	1.4388 (18)	C13—H13D	0.9900
C1—C2	1.501 (2)	C14—C15	1.532 (2)
C1—C7	1.516 (2)	C14—H14C	0.9900
C1—H1C	0.9900	C14—H14D	0.9900
C1—H1D	0.9900	C15—C16	1.5425 (19)
C2—C3	1.509 (2)	C15—C17	1.545 (2)
C2—C7	1.524 (2)	C15—C20	1.5525 (19)
C2—H2	1.0000	C16—H16D	0.9800
C3—C4	1.533 (3)	C16—H16E	0.9800
C3—H3C	0.9900	C16—H16F	0.9800
C3—H3D	0.9900	C17—C18	1.530 (2)
C4—C5	1.549 (2)	C17—H17	1.0000
C4—H4C	0.9900	C18—C19	1.551 (2)
C4—H4D	0.9900	C18—H18E	0.9900
C5—C6	1.532 (2)	C18—H18F	0.9900
C5—C7	1.535 (2)	C19—C20	1.559 (2)
C5—C12	1.5562 (19)	C19—H19C	0.9900
C6—H6D	0.9800	C19—H19D	0.9900
C6—H6E	0.9800	C20—C21	1.540 (2)
C6—H6F	0.9800	C20—H20	1.0000
C7—C8	1.507 (2)	C21—C23	1.523 (2)
C8—C10	1.520 (2)	C21—C22	1.536 (3)
C8—H8	1.0000	C21—H21	1.0000
C9—H9D	0.9800	C22—H22A	0.9800
C9—H9E	0.9800	C22—H22B	0.9800
C9—H9F	0.9800	C22—H22C	0.9800
C10—C11	1.527 (2)	C23—H23D	0.9900
C10—H10C	0.9900	C23—H23E	0.9900
C10—H10D	0.9900	C24—C25	1.503 (2)
C11—C17	1.5279 (19)	C25—H25D	0.9800
C11—C12	1.542 (2)	C25—H25E	0.9800
C11—H11	1.0000	C25—H25F	0.9800

C24—O1—C23	116.28 (12)	C12—C13—H13C	109.0
C9—O3—C8	113.69 (12)	C14—C13—H13C	109.0
C2—C1—C7	60.67 (10)	C12—C13—H13D	109.0
C2—C1—H1C	117.7	C14—C13—H13D	109.0
C7—C1—H1C	117.7	H13C—C13—H13D	107.8
C2—C1—H1D	117.7	C15—C14—C13	110.86 (13)
C7—C1—H1D	117.7	C15—C14—H14C	109.5
H1C—C1—H1D	114.8	C13—C14—H14C	109.5
C1—C2—C3	116.65 (16)	C15—C14—H14D	109.5
C1—C2—C7	60.16 (10)	C13—C14—H14D	109.5
C3—C2—C7	108.47 (15)	H14C—C14—H14D	108.1
C1—C2—H2	119.1	C14—C15—C16	110.98 (14)
C3—C2—H2	119.1	C14—C15—C17	107.23 (12)
C7—C2—H2	119.1	C16—C15—C17	112.21 (13)
C2—C3—C4	104.22 (16)	C14—C15—C20	116.41 (13)
C2—C3—H3C	110.9	C16—C15—C20	109.75 (12)
C4—C3—H3C	110.9	C17—C15—C20	99.78 (11)
C2—C3—H3D	110.9	C15—C16—H16D	109.5
C4—C3—H3D	110.9	C15—C16—H16E	109.5
H3C—C3—H3D	108.9	H16D—C16—H16E	109.5
C3—C4—C5	106.63 (14)	C15—C16—H16F	109.5
C3—C4—H4C	110.4	H16D—C16—H16F	109.5
C5—C4—H4C	110.4	H16E—C16—H16F	109.5
C3—C4—H4D	110.4	C11—C17—C18	118.76 (13)
C5—C4—H4D	110.4	C11—C17—C15	114.60 (12)
H4C—C4—H4D	108.6	C18—C17—C15	104.30 (11)
C6—C5—C7	112.04 (14)	C11—C17—H17	106.1
C6—C5—C4	111.19 (15)	C18—C17—H17	106.1
C7—C5—C4	103.00 (12)	C15—C17—H17	106.1
C6—C5—C12	112.47 (13)	C17—C18—C19	103.31 (13)
C7—C5—C12	108.54 (12)	C17—C18—H18E	111.1
C4—C5—C12	109.15 (14)	C19—C18—H18E	111.1
C5—C6—H6D	109.5	C17—C18—H18F	111.1
C5—C6—H6E	109.5	C19—C18—H18F	111.1
H6D—C6—H6E	109.5	H18E—C18—H18F	109.1
C5—C6—H6F	109.5	C18—C19—C20	106.99 (13)
H6D—C6—H6F	109.5	C18—C19—H19C	110.3
H6E—C6—H6F	109.5	C20—C19—H19C	110.3
C8—C7—C1	118.20 (14)	C18—C19—H19D	110.3
C8—C7—C2	120.24 (14)	C20—C19—H19D	110.3
C1—C7—C2	59.17 (10)	H19C—C19—H19D	108.6
C8—C7—C5	119.34 (12)	C21—C20—C15	118.22 (12)
C1—C7—C5	117.30 (14)	C21—C20—C19	112.44 (13)
C2—C7—C5	107.80 (13)	C15—C20—C19	103.36 (12)
O3—C8—C7	113.39 (13)	C21—C20—H20	107.4
O3—C8—C10	105.61 (12)	C15—C20—H20	107.4
C7—C8—C10	110.70 (13)	C19—C20—H20	107.4
O3—C8—H8	109.0	C23—C21—C22	109.58 (14)
C7—C8—H8	109.0	C23—C21—C20	108.70 (12)
C10—C8—H8	109.0	C22—C21—C20	113.40 (14)
O3—C9—H9D	109.5	C23—C21—H21	108.3
O3—C9—H9E	109.5	C22—C21—H21	108.3
H9D—C9—H9E	109.5	C20—C21—H21	108.3
O3—C9—H9F	109.5	C21—C22—H22A	109.5
H9D—C9—H9F	109.5	C21—C22—H22B	109.5
H9E—C9—H9F	109.5	H22A—C22—H22B	109.5
C8—C10—C11	112.28 (12)	C21—C22—H22C	109.5
C8—C10—H10C	109.1	H22A—C22—H22C	109.5
C11—C10—H10C	109.1	H22B—C22—H22C	109.5
C8—C10—H10D	109.1	O1—C23—C21	107.87 (12)
C11—C10—H10D	109.1	O1—C23—H23D	110.1
H10C—C10—H10D	107.9	C21—C23—H23D	110.1
C10—C11—C17	111.29 (12)	O1—C23—H23E	110.1
C10—C11—C12	110.33 (11)	C21—C23—H23E	110.1
C17—C11—C12	108.11 (12)	H23D—C23—H23E	108.4
C10—C11—H11	109.0	O2—C24—O1	123.80 (15)
C17—C11—H11	109.0	O2—C24—C25	124.99 (15)
C12—C11—H11	109.0	O1—C24—C25	111.21 (14)
C13—C12—C11	110.47 (12)	C24—C25—H25D	109.5
C13—C12—C5	112.33 (13)	C24—C25—H25E	109.5
C11—C12—C5	113.93 (13)	H25D—C25—H25E	109.5
C13—C12—H12	106.5	C24—C25—H25F	109.5
C11—C12—H12	106.5	H25D—C25—H25F	109.5
C5—C12—H12	106.5	H25E—C25—H25F	109.5
C12—C13—C14	112.90 (14)

C7—C1—C2—C3	−96.93 (17)	C4—C5—C12—C13	73.88 (17)
C1—C2—C3—C4	47.2 (2)	C6—C5—C12—C11	76.57 (17)
C7—C2—C3—C4	−18.01 (19)	C7—C5—C12—C11	−47.97 (17)
C2—C3—C4—C5	30.41 (18)	C4—C5—C12—C11	−159.54 (13)
C3—C4—C5—C6	−150.84 (15)	C11—C12—C13—C14	55.86 (19)
C3—C4—C5—C7	−30.67 (17)	C5—C12—C13—C14	−175.72 (14)
C3—C4—C5—C12	84.52 (16)	C12—C13—C14—C15	−56.96 (19)
C2—C1—C7—C8	−110.21 (16)	C13—C14—C15—C16	−67.31 (17)
C2—C1—C7—C5	95.32 (16)	C13—C14—C15—C17	55.57 (16)
C1—C2—C7—C8	106.81 (16)	C13—C14—C15—C20	166.22 (13)
C3—C2—C7—C8	−142.48 (15)	C10—C11—C17—C18	−55.54 (16)
C3—C2—C7—C1	110.71 (16)	C12—C11—C17—C18	−176.85 (13)
C1—C2—C7—C5	−111.68 (14)	C10—C11—C17—C15	−179.67 (12)
C3—C2—C7—C5	−0.96 (18)	C12—C11—C17—C15	59.02 (15)
C6—C5—C7—C8	−79.26 (17)	C14—C15—C17—C11	−59.41 (16)
C4—C5—C7—C8	161.16 (15)	C16—C15—C17—C11	62.70 (17)
C12—C5—C7—C8	45.53 (18)	C20—C15—C17—C11	178.85 (12)
C6—C5—C7—C1	74.92 (18)	C14—C15—C17—C18	169.08 (12)
C4—C5—C7—C1	−44.66 (17)	C16—C15—C17—C18	−68.81 (15)
C12—C5—C7—C1	−160.29 (13)	C20—C15—C17—C18	47.34 (14)
C6—C5—C7—C2	138.82 (14)	C11—C17—C18—C19	−163.91 (12)
C4—C5—C7—C2	19.24 (16)	C15—C17—C18—C19	−34.87 (15)
C12—C5—C7—C2	−96.40 (14)	C17—C18—C19—C20	8.70 (17)
C9—O3—C8—C7	65.98 (17)	C14—C15—C20—C21	79.65 (17)
C9—O3—C8—C10	−172.64 (14)	C16—C15—C20—C21	−47.44 (19)
C1—C7—C8—O3	−84.03 (16)	C17—C15—C20—C21	−165.44 (13)
C2—C7—C8—O3	−152.90 (13)	C14—C15—C20—C19	−155.41 (14)
C5—C7—C8—O3	69.91 (17)	C16—C15—C20—C19	77.50 (16)
C1—C7—C8—C10	157.49 (13)	C17—C15—C20—C19	−40.50 (14)
C2—C7—C8—C10	88.62 (16)	C18—C19—C20—C21	148.82 (13)
C5—C7—C8—C10	−48.57 (18)	C18—C19—C20—C15	20.22 (16)
O3—C8—C10—C11	−70.54 (16)	C15—C20—C21—C23	177.98 (14)
C7—C8—C10—C11	52.56 (16)	C19—C20—C21—C23	57.63 (17)
C8—C10—C11—C17	−177.44 (12)	C15—C20—C21—C22	−59.89 (19)
C8—C10—C11—C12	−57.44 (16)	C19—C20—C21—C22	179.76 (15)
C10—C11—C12—C13	−176.47 (13)	C24—O1—C23—C21	−174.41 (14)
C17—C11—C12—C13	−54.57 (16)	C22—C21—C23—O1	59.70 (18)
C10—C11—C12—C5	55.99 (16)	C20—C21—C23—O1	−175.88 (13)
C17—C11—C12—C5	177.89 (12)	C23—O1—C24—O2	1.3 (3)
C6—C5—C12—C13	−50.0 (2)	C23—O1—C24—C25	−179.22 (17)
C7—C5—C12—C13	−174.54 (13)

Experimental details

Crystal data
Chemical formula	C₂₅H₄₀O₃
M_r	388.57
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	9.8222 (1), 7.6128 (1), 15.2309 (2)
β (°)	107.604 (1)
V (Å³)	1085.55 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.10 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10411, 2674, 2550
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.05
No. of reflections	2674
No. of parameters	258
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–211. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ketuly, K. A. A., Hadi, A. H. & Ng, S. W. (2009). Acta Cryst. E65, o1125. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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