6β-Methyl-3,20-dioxopregn-4-en-17-yl acetate

Chen, L.; Liu, X.; Yang, P.

doi:10.1107/S1600536812008665

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o997

doi:10.1107/S1600536812008665

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6β-Methyl-3,20-dioxopregn-4-en-17-yl acetate

Longran Chen,^a Xuefen Liu ^a ^* and Peng Yang ^a

^aQianjiang Colloge, Hangzhou Normal University, Hangzhou 310012, People's Republic of China
^*Correspondence e-mail: Hdliuxf@tom.com

(Received 15 January 2012; accepted 27 February 2012; online 10 March 2012)

The title compound, C₂₄H₃₄O₄, is a precursor of Megestrol acetate. Ring A has a half-chair conformation [Q = 0.446 (3) Å, θ = 54.6 (4)° and φ = 9.5 (4)°]. Ring D adopts a 13β-envelope conformation [Q = 0.463 (2) Å and φ = 188.2 (3)°].

Related literature

For the characterization of related structures, see: Evans & Boeyens (1989 ). Soriano-Garcia et al. (2005 ). Yousuf et al. (2011 ). For the physiological properties of the title compound, see: Mishell (1996 ).

Experimental

Crystal data

C₂₄H₃₄O₄
M_r = 386.51
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.0411 (3) Å
b = 11.3123 (3) Å
c = 18.5549 (7) Å
V = 2107.61 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.56 × 0.52 × 0.31 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.946, T_max = 0.975
20014 measured reflections
2679 independent reflections
2108 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.00
2679 reflections
259 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008665/ld2047sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008665/ld2047Isup2.hkl

checkCIF report

Comment top

6β-methyl-3,20-dioxopregn-4-ene-17-yl acetate and its derivatives (for example, Megestrol acetate) are important progestines used for the treatment of endomentriosis as well as several other applications (Mishell, 1996).

The structure of the title compound is depicted in Fig.1. Ring A (C1—C5, C10) has a slightly distorted half-chair conformation with Q (total puckering amplitude) = 0.446 (3) Å, theta (azimuthal angle) = 54.6 (4) °, φ (phase angle) = 9.5 (4) °, while ring B (C5—C10) and C (C8,C9, C11—C14) are in chair conformation [ring B: Q = 0.521 (2) Å, theta = 12.7 (2) °, φ = 188.7 (13) °; ring C: Q = 0.564 (2) Å, theta = 2.8 (2) °, φ = 267 (4) °] (Evans & Boeyens, 1989). The five-membered ring D exhibits a 13β-envelope conformation with puckering amplitude Q = 0.463 (2) Å and phase angle= 188.2 (3) °. The crystals are isomorphous to 17alpha-Acetoxy-6-methylene-4-pregnene-3,20-dione (Soriano-Garcia et al., 2005). The crystal structure is also similar to 3alpha-Dimethylamino-20-(N-methylacetamido)pregn-5-ene (Yousuf et al., 2011).

Related literature top

For the characterization of related structures, see: Evans & Boeyens (1989). Soriano-Garcia et al. (2005). Yousuf et al. (2011). For the physiological properties of the title compound, see: Mishell (1996).

Experimental top

The title compound was received from Shanghai Xinhualian Pharmaceutical Co., Ltd. Suitable crystals were obtained by slow evaporation of its ethanol solution at room temperature.

Structure description top

For the characterization of related structures, see: Evans & Boeyens (1989). Soriano-Garcia et al. (2005). Yousuf et al. (2011). For the physiological properties of the title compound, see: Mishell (1996).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

6β-Methyl-3,20-dioxopregn-4-en-17-yl acetate top

Crystal data top

C₂₄H₃₄O₄	F(000) = 840
M_r = 386.51	D_x = 1.218 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14918 reflections
a = 10.0411 (3) Å	θ = 3.0–27.4°
b = 11.3123 (3) Å	µ = 0.08 mm⁻¹
c = 18.5549 (7) Å	T = 296 K
V = 2107.61 (12) Å³	Chunk, colorless
Z = 4	0.56 × 0.52 × 0.31 mm

Data collection top

Rigaku R-AXIS RAPID/ZJUG diffractometer	2679 independent reflections
Radiation source: rolling anode	2108 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.4°, θ_min = 3.0°
ω scans	h = −12→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
T_min = 0.946, T_max = 0.975	l = −24→24
20014 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0441P)² + 0.5695P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2679 reflections	Δρ_max = 0.17 e Å⁻³
259 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (12)

Crystal data top

C₂₄H₃₄O₄	V = 2107.61 (12) Å³
M_r = 386.51	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.0411 (3) Å	µ = 0.08 mm⁻¹
b = 11.3123 (3) Å	T = 296 K
c = 18.5549 (7) Å	0.56 × 0.52 × 0.31 mm

Data collection top

Rigaku R-AXIS RAPID/ZJUG diffractometer	2679 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2108 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.975	R_int = 0.035
20014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
2679 reflections	Δρ_min = −0.16 e Å⁻³
259 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.9284 (2)	−0.06142 (15)	0.53897 (13)	0.0759 (7)
O2	0.6725 (3)	0.92350 (17)	0.70081 (12)	0.0713 (6)
O3	0.49550 (16)	0.66587 (14)	0.65423 (9)	0.0439 (4)
O4	0.3669 (2)	0.82806 (18)	0.65415 (12)	0.0655 (6)
C1	0.8845 (3)	0.1906 (2)	0.65614 (14)	0.0475 (6)
H1A	0.9083	0.2115	0.7052	0.057*
H1B	0.7889	0.1785	0.6547	0.057*
C2	0.9537 (3)	0.0745 (2)	0.63640 (16)	0.0572 (7)
H2A	1.0487	0.0825	0.6445	0.069*
H2B	0.9210	0.0120	0.6676	0.069*
C3	0.9299 (3)	0.0410 (2)	0.55974 (17)	0.0533 (7)
C4	0.9105 (3)	0.1385 (2)	0.50972 (15)	0.0499 (6)
H4	0.8976	0.1195	0.4615	0.060*
C5	0.9097 (2)	0.2534 (2)	0.52737 (13)	0.0407 (5)
C6	0.8994 (3)	0.3438 (2)	0.46795 (14)	0.0461 (6)
H6	0.8611	0.3028	0.4263	0.055*
C7	0.8027 (3)	0.4433 (2)	0.48694 (13)	0.0447 (6)
H7A	0.8107	0.5055	0.4512	0.054*
H7B	0.7124	0.4130	0.4848	0.054*
C8	0.8270 (2)	0.49588 (19)	0.56153 (12)	0.0368 (5)
H8	0.9157	0.5320	0.5629	0.044*
C9	0.8186 (2)	0.39747 (19)	0.61904 (12)	0.0373 (5)
H9	0.7299	0.3622	0.6139	0.045*
C10	0.9205 (2)	0.29462 (19)	0.60597 (13)	0.0388 (5)
C11	0.8245 (3)	0.4476 (2)	0.69591 (12)	0.0441 (6)
H11A	0.8099	0.3838	0.7299	0.053*
H11B	0.9129	0.4791	0.7045	0.053*
C12	0.7216 (3)	0.5454 (2)	0.71000 (13)	0.0443 (6)
H12A	0.6327	0.5120	0.7083	0.053*
H12B	0.7354	0.5779	0.7578	0.053*
C13	0.7333 (2)	0.64437 (19)	0.65394 (13)	0.0362 (5)
C14	0.7224 (2)	0.58932 (19)	0.57819 (12)	0.0360 (5)
H14	0.6363	0.5487	0.5768	0.043*
C15	0.7092 (3)	0.69619 (19)	0.52808 (13)	0.0436 (6)
H15A	0.6611	0.6753	0.4846	0.052*
H15B	0.7961	0.7267	0.5149	0.052*
C16	0.6308 (3)	0.7875 (2)	0.57264 (13)	0.0441 (6)
H16A	0.5437	0.8007	0.5515	0.053*
H16B	0.6782	0.8622	0.5740	0.053*
C17	0.6167 (2)	0.7366 (2)	0.64927 (13)	0.0393 (5)
C22	1.0348 (3)	0.3910 (3)	0.44369 (17)	0.0646 (8)
H18A	1.0727	0.4386	0.4814	0.097*
H18B	1.0237	0.4383	0.4011	0.097*
H18C	1.0931	0.3260	0.4334	0.097*
C19	1.0656 (2)	0.3338 (2)	0.62124 (16)	0.0507 (6)
H19A	1.0760	0.3491	0.6718	0.076*
H19B	1.0848	0.4045	0.5945	0.076*
H19C	1.1257	0.2723	0.6068	0.076*
C18	0.8651 (3)	0.7121 (2)	0.66410 (15)	0.0493 (6)
H20A	0.8674	0.7463	0.7114	0.074*
H20B	0.8715	0.7735	0.6286	0.074*
H20C	0.9386	0.6585	0.6586	0.074*
C20	0.6198 (3)	0.8284 (2)	0.70979 (15)	0.0507 (6)
C21	0.5662 (4)	0.7928 (3)	0.78251 (15)	0.0689 (9)
H22A	0.6221	0.8248	0.8197	0.103*
H22B	0.5651	0.7081	0.7861	0.103*
H22C	0.4773	0.8227	0.7880	0.103*
C23	0.3771 (3)	0.7220 (3)	0.65162 (15)	0.0502 (6)
C24	0.2663 (3)	0.6356 (3)	0.6461 (2)	0.0717 (9)
H24A	0.1828	0.6766	0.6486	0.108*
H24B	0.2722	0.5800	0.6851	0.108*
H24C	0.2724	0.5943	0.6010	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0979 (17)	0.0353 (10)	0.0944 (16)	−0.0064 (10)	0.0245 (14)	−0.0033 (10)
O2	0.0876 (16)	0.0496 (11)	0.0766 (14)	−0.0048 (11)	0.0016 (13)	−0.0149 (10)
O3	0.0355 (9)	0.0459 (9)	0.0503 (9)	0.0016 (7)	0.0036 (8)	0.0031 (8)
O4	0.0601 (12)	0.0629 (12)	0.0734 (13)	0.0205 (10)	0.0049 (12)	0.0007 (11)
C1	0.0506 (14)	0.0424 (12)	0.0495 (14)	0.0014 (11)	0.0012 (13)	0.0087 (11)
C2	0.0604 (17)	0.0420 (13)	0.0692 (19)	0.0045 (12)	0.0028 (14)	0.0098 (13)
C3	0.0484 (15)	0.0385 (13)	0.0729 (19)	−0.0019 (11)	0.0133 (14)	0.0025 (13)
C4	0.0523 (16)	0.0423 (13)	0.0552 (15)	−0.0034 (11)	0.0058 (13)	−0.0045 (11)
C5	0.0352 (13)	0.0393 (11)	0.0474 (13)	−0.0006 (10)	0.0043 (11)	0.0000 (10)
C6	0.0541 (15)	0.0419 (12)	0.0424 (13)	0.0001 (11)	0.0059 (12)	−0.0013 (10)
C7	0.0543 (15)	0.0425 (12)	0.0373 (12)	0.0042 (12)	0.0007 (11)	0.0025 (10)
C8	0.0384 (12)	0.0354 (11)	0.0365 (12)	−0.0014 (9)	0.0027 (10)	0.0020 (9)
C9	0.0364 (12)	0.0365 (11)	0.0389 (12)	−0.0004 (9)	0.0011 (10)	0.0024 (9)
C10	0.0379 (13)	0.0354 (11)	0.0432 (13)	−0.0005 (10)	0.0006 (10)	0.0024 (10)
C11	0.0502 (14)	0.0445 (13)	0.0377 (12)	0.0076 (11)	0.0003 (11)	0.0037 (10)
C12	0.0511 (15)	0.0468 (13)	0.0350 (12)	0.0062 (11)	0.0044 (11)	0.0055 (10)
C13	0.0370 (12)	0.0376 (11)	0.0341 (11)	0.0020 (9)	0.0009 (10)	0.0020 (9)
C14	0.0389 (12)	0.0350 (11)	0.0341 (12)	−0.0006 (9)	−0.0001 (10)	0.0038 (9)
C15	0.0525 (14)	0.0392 (12)	0.0390 (12)	0.0024 (11)	0.0031 (11)	0.0067 (10)
C16	0.0476 (14)	0.0396 (12)	0.0452 (13)	0.0045 (11)	0.0028 (11)	0.0075 (10)
C17	0.0389 (12)	0.0382 (11)	0.0407 (12)	−0.0004 (10)	0.0004 (11)	−0.0006 (10)
C22	0.070 (2)	0.0561 (16)	0.0677 (19)	0.0004 (14)	0.0255 (16)	0.0074 (15)
C19	0.0370 (13)	0.0499 (14)	0.0651 (17)	0.0009 (11)	−0.0039 (12)	−0.0018 (13)
C18	0.0437 (14)	0.0479 (13)	0.0563 (16)	−0.0037 (11)	−0.0046 (12)	−0.0065 (12)
C20	0.0540 (15)	0.0480 (14)	0.0502 (15)	0.0101 (13)	−0.0013 (13)	−0.0058 (12)
C21	0.087 (2)	0.074 (2)	0.0448 (16)	0.0202 (18)	0.0032 (16)	−0.0082 (14)
C23	0.0421 (14)	0.0628 (17)	0.0457 (14)	0.0108 (12)	0.0045 (12)	0.0053 (13)
C24	0.0409 (15)	0.088 (2)	0.086 (2)	−0.0019 (15)	0.0033 (16)	0.0111 (19)

Geometric parameters (Å, º) top

O1—C3	1.221 (3)	C12—C13	1.533 (3)
O2—C20	1.210 (3)	C12—H12A	0.9700
O3—C23	1.348 (3)	C12—H12B	0.9700
O3—C17	1.459 (3)	C13—C18	1.540 (3)
O4—C23	1.205 (3)	C13—C14	1.541 (3)
C1—C2	1.530 (3)	C13—C17	1.571 (3)
C1—C10	1.544 (3)	C14—C15	1.531 (3)
C1—H1A	0.9700	C14—H14	0.9800
C1—H1B	0.9700	C15—C16	1.539 (3)
C2—C3	1.491 (4)	C15—H15A	0.9700
C2—H2A	0.9700	C15—H15B	0.9700
C2—H2B	0.9700	C16—C17	1.540 (3)
C3—C4	1.455 (4)	C16—H16A	0.9700
C4—C5	1.341 (3)	C16—H16B	0.9700
C4—H4	0.9300	C17—C20	1.530 (3)
C5—C6	1.508 (3)	C22—H18A	0.9600
C5—C10	1.535 (3)	C22—H18B	0.9600
C6—C7	1.527 (3)	C22—H18C	0.9600
C6—C22	1.529 (4)	C19—H19A	0.9600
C6—H6	0.9800	C19—H19B	0.9600
C7—C8	1.526 (3)	C19—H19C	0.9600
C7—H7A	0.9700	C18—H20A	0.9600
C7—H7B	0.9700	C18—H20B	0.9600
C8—C14	1.522 (3)	C18—H20C	0.9600
C8—C9	1.544 (3)	C20—C21	1.508 (4)
C8—H8	0.9800	C21—H22A	0.9600
C9—C11	1.536 (3)	C21—H22B	0.9600
C9—C10	1.568 (3)	C21—H22C	0.9600
C9—H9	0.9800	C23—C24	1.485 (4)
C10—C19	1.549 (3)	C24—H24A	0.9600
C11—C12	1.536 (3)	C24—H24B	0.9600
C11—H11A	0.9700	C24—H24C	0.9600
C11—H11B	0.9700

C23—O3—C17	118.33 (17)	C12—C13—C14	108.56 (18)
C2—C1—C10	113.8 (2)	C18—C13—C14	111.9 (2)
C2—C1—H1A	108.8	C12—C13—C17	117.73 (19)
C10—C1—H1A	108.8	C18—C13—C17	108.48 (18)
C2—C1—H1B	108.8	C14—C13—C17	99.50 (18)
C10—C1—H1B	108.8	C8—C14—C15	119.02 (19)
H1A—C1—H1B	107.7	C8—C14—C13	114.65 (19)
C3—C2—C1	112.0 (2)	C15—C14—C13	103.95 (17)
C3—C2—H2A	109.2	C8—C14—H14	106.1
C1—C2—H2A	109.2	C15—C14—H14	106.1
C3—C2—H2B	109.2	C13—C14—H14	106.1
C1—C2—H2B	109.2	C14—C15—C16	104.36 (18)
H2A—C2—H2B	107.9	C14—C15—H15A	110.9
O1—C3—C4	121.1 (3)	C16—C15—H15A	110.9
O1—C3—C2	123.0 (3)	C14—C15—H15B	110.9
C4—C3—C2	115.9 (2)	C16—C15—H15B	110.9
C5—C4—C3	125.5 (3)	H15A—C15—H15B	108.9
C5—C4—H4	117.3	C15—C16—C17	106.98 (18)
C3—C4—H4	117.3	C15—C16—H16A	110.3
C4—C5—C6	118.7 (2)	C17—C16—H16A	110.3
C4—C5—C10	121.7 (2)	C15—C16—H16B	110.3
C6—C5—C10	119.59 (19)	C17—C16—H16B	110.3
C5—C6—C7	112.0 (2)	H16A—C16—H16B	108.6
C5—C6—C22	113.0 (2)	O3—C17—C20	110.0 (2)
C7—C6—C22	112.1 (2)	O3—C17—C16	109.87 (19)
C5—C6—H6	106.4	C20—C17—C16	114.95 (19)
C7—C6—H6	106.4	O3—C17—C13	104.72 (16)
C22—C6—H6	106.4	C20—C17—C13	113.3 (2)
C8—C7—C6	113.3 (2)	C16—C17—C13	103.33 (19)
C8—C7—H7A	108.9	C6—C22—H18A	109.5
C6—C7—H7A	108.9	C6—C22—H18B	109.5
C8—C7—H7B	108.9	H18A—C22—H18B	109.5
C6—C7—H7B	108.9	C6—C22—H18C	109.5
H7A—C7—H7B	107.7	H18A—C22—H18C	109.5
C14—C8—C7	110.18 (19)	H18B—C22—H18C	109.5
C14—C8—C9	108.82 (18)	C10—C19—H19A	109.5
C7—C8—C9	109.70 (18)	C10—C19—H19B	109.5
C14—C8—H8	109.4	H19A—C19—H19B	109.5
C7—C8—H8	109.4	C10—C19—H19C	109.5
C9—C8—H8	109.4	H19A—C19—H19C	109.5
C11—C9—C8	111.91 (18)	H19B—C19—H19C	109.5
C11—C9—C10	113.11 (19)	C13—C18—H20A	109.5
C8—C9—C10	113.10 (18)	C13—C18—H20B	109.5
C11—C9—H9	106.0	H20A—C18—H20B	109.5
C8—C9—H9	106.0	C13—C18—H20C	109.5
C10—C9—H9	106.0	H20A—C18—H20C	109.5
C5—C10—C1	108.96 (19)	H20B—C18—H20C	109.5
C5—C10—C19	109.1 (2)	O2—C20—C21	121.1 (3)
C1—C10—C19	109.2 (2)	O2—C20—C17	120.7 (2)
C5—C10—C9	109.04 (19)	C21—C20—C17	117.9 (2)
C1—C10—C9	108.65 (19)	C20—C21—H22A	109.5
C19—C10—C9	111.90 (19)	C20—C21—H22B	109.5
C12—C11—C9	113.5 (2)	H22A—C21—H22B	109.5
C12—C11—H11A	108.9	C20—C21—H22C	109.5
C9—C11—H11A	108.9	H22A—C21—H22C	109.5
C12—C11—H11B	108.9	H22B—C21—H22C	109.5
C9—C11—H11B	108.9	O4—C23—O3	122.9 (3)
H11A—C11—H11B	107.7	O4—C23—C24	126.4 (3)
C13—C12—C11	111.03 (19)	O3—C23—C24	110.7 (2)
C13—C12—H12A	109.4	C23—C24—H24A	109.5
C11—C12—H12A	109.4	C23—C24—H24B	109.5
C13—C12—H12B	109.4	H24A—C24—H24B	109.5
C11—C12—H12B	109.4	C23—C24—H24C	109.5
H12A—C12—H12B	108.0	H24A—C24—H24C	109.5
C12—C13—C18	110.2 (2)	H24B—C24—H24C	109.5

C10—C1—C2—C3	−54.3 (3)	C11—C12—C13—C14	54.6 (3)
C1—C2—C3—O1	−151.0 (3)	C11—C12—C13—C17	166.5 (2)
C1—C2—C3—C4	30.0 (3)	C7—C8—C14—C15	−58.9 (3)
O1—C3—C4—C5	179.6 (3)	C9—C8—C14—C15	−179.2 (2)
C2—C3—C4—C5	−1.4 (4)	C7—C8—C14—C13	177.23 (19)
C3—C4—C5—C6	175.1 (2)	C9—C8—C14—C13	56.9 (2)
C3—C4—C5—C10	−4.2 (4)	C12—C13—C14—C8	−58.6 (2)
C4—C5—C6—C7	137.0 (3)	C18—C13—C14—C8	63.3 (2)
C10—C5—C6—C7	−43.6 (3)	C17—C13—C14—C8	177.79 (18)
C4—C5—C6—C22	−95.2 (3)	C12—C13—C14—C15	169.82 (19)
C10—C5—C6—C22	84.1 (3)	C18—C13—C14—C15	−68.3 (2)
C5—C6—C7—C8	49.1 (3)	C17—C13—C14—C15	46.2 (2)
C22—C6—C7—C8	−79.2 (3)	C8—C14—C15—C16	−162.4 (2)
C6—C7—C8—C14	−176.85 (19)	C13—C14—C15—C16	−33.4 (2)
C6—C7—C8—C9	−57.1 (3)	C14—C15—C16—C17	6.7 (3)
C14—C8—C9—C11	−52.1 (3)	C23—O3—C17—C20	58.0 (3)
C7—C8—C9—C11	−172.7 (2)	C23—O3—C17—C16	−69.5 (2)
C14—C8—C9—C10	178.72 (19)	C23—O3—C17—C13	−179.9 (2)
C7—C8—C9—C10	58.1 (3)	C15—C16—C17—O3	−89.6 (2)
C4—C5—C10—C1	−18.7 (3)	C15—C16—C17—C20	145.7 (2)
C6—C5—C10—C1	161.9 (2)	C15—C16—C17—C13	21.8 (2)
C4—C5—C10—C19	100.4 (3)	C12—C13—C17—O3	−43.0 (3)
C6—C5—C10—C19	−79.0 (3)	C18—C13—C17—O3	−169.06 (19)
C4—C5—C10—C9	−137.2 (2)	C14—C13—C17—O3	73.86 (19)
C6—C5—C10—C9	43.5 (3)	C12—C13—C17—C20	76.9 (3)
C2—C1—C10—C5	47.2 (3)	C18—C13—C17—C20	−49.1 (3)
C2—C1—C10—C19	−71.8 (3)	C14—C13—C17—C20	−166.2 (2)
C2—C1—C10—C9	165.9 (2)	C12—C13—C17—C16	−158.1 (2)
C11—C9—C10—C5	−178.3 (2)	C18—C13—C17—C16	75.9 (2)
C8—C9—C10—C5	−49.8 (2)	C14—C13—C17—C16	−41.2 (2)
C11—C9—C10—C1	63.1 (3)	O3—C17—C20—O2	−148.1 (3)
C8—C9—C10—C1	−168.4 (2)	C16—C17—C20—O2	−23.4 (4)
C11—C9—C10—C19	−57.5 (3)	C13—C17—C20—O2	95.1 (3)
C8—C9—C10—C19	71.0 (3)	O3—C17—C20—C21	37.2 (3)
C8—C9—C11—C12	52.9 (3)	C16—C17—C20—C21	161.9 (3)
C10—C9—C11—C12	−177.95 (19)	C13—C17—C20—C21	−79.6 (3)
C9—C11—C12—C13	−54.2 (3)	C17—O3—C23—O4	−9.2 (4)
C11—C12—C13—C18	−68.4 (2)	C17—O3—C23—C24	171.3 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₃₄O₄
M_r	386.51
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	10.0411 (3), 11.3123 (3), 18.5549 (7)
V (Å³)	2107.61 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.56 × 0.52 × 0.31

Data collection
Diffractometer	Rigaku R-AXIS RAPID/ZJUG
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.946, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	20014, 2679, 2108
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.00
No. of reflections	2679
No. of parameters	259
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

The authors thank Mr Jianming Gu for the single-crystal X-ray analysis. They are also grateful for financial support from the Qianjiang College Foundation project subsidization (2008QJSY02 and YS03204033001).

References

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