17α-Ethynyl-3-methoxy­estra-1,3,5(10),9(11)-tetraen-17-ol

Li, H.; Song, Y.; Ge, F.

doi:10.1107/S1600536808005254

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o783

doi:10.1107/S1600536808005254

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17α-Ethynyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol

Hongqi Li,^a ^* Yanxi Song ^b and Fengyan Ge ^a

^aCollege of Chemistry and Chemical Engineering, Donghua University, Shanghai 201620, People's Republic of China, and ^bCollege of Environmental Science and Engineering, Donghua University, Shanghai 201620, People's Republic of China
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 14 January 2008; accepted 25 February 2008; online 2 April 2008)

In the title compound, C₂₁H₂₄O₂, rings B, C and D adopt half-chair, distorted half-chair and envelope conformations, respectively. In the crystal structure, there is an intermolecular O—H⋯O hydrogen bond. The molecules are arranged in a head-to-tail fashion, with the methoxy and hydroxy groups forming a two-dimensional hydrogen-bond network.

Related literature

For related literature, see: Doussot et al. (1995 ); Ekhato et al. (2002 ); Sedee et al. (1985 ); Steiner et al. (1997 ).

Experimental

Crystal data

C₂₁H₂₄O₂
M_r = 308.40
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3773 (6) Å
b = 10.7430 (9) Å
c = 21.2555 (18) Å
V = 1684.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.50 × 0.43 × 0.34 mm

Data collection

Rigaku FCR CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.824, T_max = 1.000 (expected range = 0.802–0.974)
9960 measured reflections
2127 independent reflections
1884 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.114
S = 1.03
2127 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H3⋯O1ⁱ	0.82 (4)	2.14 (4)	2.933 (3)	163 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005254/wn2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005254/wn2237Isup2.hkl

checkCIF report

Comment top

The title compound is a photodecomposition product of mestranol (Sedee et al., 1985) and can be used as an intermediate for the synthesis of steroidal drugs. The preparation of the title compound starting from mestranol, through an oxidative dehydrogenation with 2,3-dichloro-5,6-dicyanoquinone (DDQ) in methanol, was reported by Doussot et al. (1995) However, no crystal structure of the title compound has been reported thus far. Here we present the crystal structure of 17α-ethinyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol.

The geometry (Fig. 1) of the steroid skeleton does not differ significantly from that of mestranol (Steiner et al., 1997), except, of course, for the C?C bond in ring C. There is an intermolecular hydrogen bond O2—H3···O1, but no intra- or intermolecular hydrogen bonding between hydroxy and ethynyl groups is observed. The molecules are arranged in a head-to-tail fashion, different from the head-to-head fashion observed in mestranol, with the methoxy and hydroxy groups forming a two-dimensional hydrogen bond network (Fig. 2).

Related literature top

For related literature, see: Doussot et al. (1995); Ekhato et al. (2002); Sedee et al. (1985); Steiner et al. (1997).

Experimental top

The title compound was prepared, in 90% yield, by methylation of 3,17β-dihydroxy-19-norpregna-1,3,5(10),9(11)-tetraen-20-yne (Ekhato et al., 2002) with methyl iodide and potassium carbonate at room temperature. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in ethyl acetate and petroleum ether (1:1, v/v).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. Dashed lines indicate hydrogen bonds

17α-Ethynyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol top

Crystal data top

C₂₁H₂₄O₂	D_x = 1.216 Mg m⁻³
M_r = 308.40	Melting point: 145 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.3773 (6) Å	Cell parameters from 3971 reflections
b = 10.7430 (9) Å	θ = 5.4–53.4°
c = 21.2555 (18) Å	µ = 0.08 mm⁻¹
V = 1684.6 (2) Å³	T = 293 K
Z = 4	Prismatic, colorless
F(000) = 664	0.50 × 0.43 × 0.35 mm

Data collection top

Rigaku FCR CCD area-detector diffractometer	2127 independent reflections
Radiation source: fine-focus sealed tube	1884 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→9
T_min = 0.824, T_max = 1.000	k = −13→9
9960 measured reflections	l = −25→27

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0757P)² + 0.0067P] where P = (F_o² + 2F_c²)/3
2127 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₄O₂	V = 1684.6 (2) Å³
M_r = 308.40	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3773 (6) Å	µ = 0.08 mm⁻¹
b = 10.7430 (9) Å	T = 293 K
c = 21.2555 (18) Å	0.50 × 0.43 × 0.35 mm

Data collection top

Rigaku FCR CCD area-detector diffractometer	2127 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1884 reflections with I > 2σ(I)
T_min = 0.824, T_max = 1.000	R_int = 0.071
9960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
2127 reflections	Δρ_min = −0.24 e Å⁻³
214 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	0.3222 (3)	0.77612 (18)	0.73106 (7)	0.0684 (5)
O2	0.5307 (3)	0.26039 (16)	1.17027 (8)	0.0583 (5)
C1	0.2555 (3)	0.6031 (2)	0.87459 (10)	0.0502 (5)
H1	0.1618	0.5584	0.8932	0.060*
C2	0.2245 (3)	0.6607 (2)	0.81810 (10)	0.0556 (6)
H2	0.1108	0.6561	0.7994	0.067*
C3	0.3626 (3)	0.7256 (2)	0.78916 (10)	0.0497 (5)
C4	0.5296 (3)	0.7326 (2)	0.81737 (10)	0.0503 (5)
H4	0.6227	0.7762	0.7978	0.060*
C5	0.5612 (3)	0.67502 (19)	0.87522 (10)	0.0422 (5)
C6	0.7485 (3)	0.6809 (2)	0.90286 (11)	0.0548 (6)
H6A	0.7993	0.7628	0.8951	0.066*
H6B	0.8250	0.6203	0.8820	0.066*
C7	0.7495 (3)	0.6558 (2)	0.97282 (11)	0.0496 (5)
H7A	0.6936	0.7251	0.9947	0.059*
H7B	0.8737	0.6487	0.9873	0.059*
C8	0.6478 (2)	0.53696 (19)	0.98837 (9)	0.0362 (4)
H8	0.7043	0.4684	0.9652	0.043*
C9	0.4518 (3)	0.54791 (17)	0.96698 (9)	0.0345 (4)
C10	0.4221 (3)	0.60908 (18)	0.90521 (9)	0.0380 (4)
C11	0.3154 (3)	0.50772 (19)	1.00285 (9)	0.0376 (4)
H11	0.1985	0.5207	0.9878	0.045*
C12	0.3331 (3)	0.44369 (19)	1.06504 (9)	0.0379 (4)
H12A	0.2522	0.3726	1.0663	0.045*
H12B	0.2980	0.5004	1.0984	0.045*
C13	0.5267 (3)	0.40034 (17)	1.07587 (8)	0.0358 (4)
C14	0.6545 (3)	0.50617 (18)	1.05775 (9)	0.0369 (4)
H14	0.6133	0.5804	1.0804	0.044*
C15	0.8389 (3)	0.4696 (2)	1.08594 (10)	0.0517 (6)
H15A	0.9140	0.4288	1.0547	0.062*
H15B	0.9023	0.5424	1.1015	0.062*
C16	0.7939 (3)	0.3803 (3)	1.13995 (11)	0.0572 (6)
H16A	0.8467	0.4097	1.1790	0.069*
H16B	0.8408	0.2978	1.1311	0.069*
C17	0.5855 (3)	0.3774 (2)	1.14476 (10)	0.0447 (5)
C18	0.5615 (3)	0.28188 (19)	1.03758 (9)	0.0471 (5)
H18A	0.5295	0.2962	0.9944	0.071*
H18B	0.4893	0.2151	1.0541	0.071*
H18C	0.6874	0.2601	1.0402	0.071*
C20	0.4291 (5)	0.8770 (3)	0.70975 (14)	0.0782 (9)
H19A	0.5512	0.8493	0.7030	0.117*
H19B	0.4284	0.9419	0.7408	0.117*
H19C	0.3801	0.9083	0.6710	0.117*
C21	0.5210 (3)	0.4781 (2)	1.18698 (9)	0.0500 (5)
C22	0.4707 (4)	0.5547 (3)	1.22112 (11)	0.0644 (7)
H21	0.4303	0.6162	1.2485	0.077*
H3	0.425 (5)	0.260 (3)	1.1812 (13)	0.079 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0730 (12)	0.0800 (12)	0.0523 (9)	0.0059 (10)	0.0010 (9)	0.0254 (8)
O2	0.0669 (13)	0.0551 (10)	0.0528 (9)	0.0104 (9)	0.0036 (8)	0.0111 (7)
C1	0.0378 (11)	0.0683 (14)	0.0445 (11)	−0.0046 (11)	0.0001 (9)	0.0071 (10)
C2	0.0426 (12)	0.0772 (16)	0.0472 (12)	0.0009 (12)	−0.0074 (9)	0.0103 (12)
C3	0.0527 (12)	0.0535 (12)	0.0429 (11)	0.0087 (11)	0.0024 (9)	0.0062 (10)
C4	0.0492 (13)	0.0485 (12)	0.0532 (12)	−0.0034 (10)	0.0119 (10)	0.0080 (10)
C5	0.0393 (11)	0.0396 (10)	0.0477 (11)	−0.0016 (8)	0.0050 (9)	−0.0006 (9)
C6	0.0379 (11)	0.0630 (14)	0.0634 (14)	−0.0149 (11)	0.0014 (10)	0.0112 (12)
C7	0.0365 (10)	0.0542 (12)	0.0580 (13)	−0.0110 (10)	−0.0068 (9)	0.0003 (10)
C8	0.0274 (8)	0.0414 (10)	0.0396 (10)	−0.0003 (8)	0.0002 (7)	−0.0059 (8)
C9	0.0311 (9)	0.0332 (9)	0.0392 (9)	−0.0010 (8)	−0.0021 (7)	−0.0051 (7)
C10	0.0350 (10)	0.0392 (10)	0.0399 (9)	0.0004 (8)	0.0028 (8)	−0.0037 (8)
C11	0.0276 (8)	0.0424 (10)	0.0429 (10)	0.0019 (8)	−0.0013 (8)	−0.0005 (8)
C12	0.0321 (10)	0.0410 (10)	0.0406 (10)	−0.0013 (8)	0.0003 (8)	−0.0013 (8)
C13	0.0342 (9)	0.0373 (9)	0.0358 (9)	0.0037 (8)	−0.0004 (7)	−0.0044 (7)
C14	0.0301 (9)	0.0410 (10)	0.0397 (9)	0.0024 (8)	−0.0031 (7)	−0.0086 (8)
C15	0.0348 (11)	0.0690 (15)	0.0515 (12)	0.0035 (11)	−0.0083 (9)	−0.0047 (11)
C16	0.0463 (12)	0.0728 (16)	0.0525 (13)	0.0130 (12)	−0.0124 (10)	0.0021 (11)
C17	0.0474 (11)	0.0477 (11)	0.0390 (10)	0.0075 (10)	−0.0031 (8)	0.0003 (9)
C18	0.0522 (12)	0.0395 (10)	0.0496 (11)	0.0024 (10)	0.0042 (10)	−0.0091 (9)
C20	0.101 (2)	0.0648 (16)	0.0685 (16)	0.0106 (18)	0.0222 (16)	0.0199 (13)
C21	0.0557 (13)	0.0572 (13)	0.0369 (10)	−0.0028 (11)	−0.0062 (9)	−0.0045 (10)
C22	0.0740 (17)	0.0709 (16)	0.0482 (12)	0.0020 (15)	−0.0018 (12)	−0.0185 (12)

Geometric parameters (Å, º) top

O1—C3	1.381 (3)	C11—C12	1.496 (3)
O1—C20	1.415 (4)	C11—H11	0.9300
O2—C17	1.428 (3)	C12—C13	1.520 (3)
O2—H3	0.82 (4)	C12—H12A	0.9700
C1—C2	1.370 (3)	C12—H12B	0.9700
C1—C10	1.392 (3)	C13—C14	1.526 (3)
C1—H1	0.9300	C13—C18	1.532 (3)
C2—C3	1.379 (3)	C13—C17	1.547 (3)
C2—H2	0.9300	C14—C15	1.538 (3)
C3—C4	1.373 (3)	C14—H14	0.9800
C4—C5	1.396 (3)	C15—C16	1.532 (3)
C4—H4	0.9300	C15—H15A	0.9700
C5—C10	1.400 (3)	C15—H15B	0.9700
C5—C6	1.503 (3)	C16—C17	1.542 (3)
C6—C7	1.511 (3)	C16—H16A	0.9700
C6—H6A	0.9700	C16—H16B	0.9700
C6—H6B	0.9700	C17—C21	1.483 (3)
C7—C8	1.517 (3)	C18—H18A	0.9600
C7—H7A	0.9700	C18—H18B	0.9600
C7—H7B	0.9700	C18—H18C	0.9600
C8—C14	1.512 (3)	C20—H19A	0.9600
C8—C9	1.520 (2)	C20—H19B	0.9600
C8—H8	0.9800	C20—H19C	0.9600
C9—C11	1.334 (3)	C21—C22	1.159 (3)
C9—C10	1.484 (3)	C22—H21	0.9300

C3—O1—C20	117.8 (2)	C11—C12—H12B	109.5
C17—O2—H3	113 (2)	C13—C12—H12B	109.5
C2—C1—C10	122.4 (2)	H12A—C12—H12B	108.0
C2—C1—H1	118.8	C12—C13—C14	108.29 (15)
C10—C1—H1	118.8	C12—C13—C18	109.35 (17)
C1—C2—C3	119.7 (2)	C14—C13—C18	112.42 (16)
C1—C2—H2	120.1	C12—C13—C17	117.09 (16)
C3—C2—H2	120.1	C14—C13—C17	100.62 (15)
C4—C3—C2	119.7 (2)	C18—C13—C17	108.90 (16)
C4—C3—O1	124.2 (2)	C8—C14—C13	112.88 (15)
C2—C3—O1	116.0 (2)	C8—C14—C15	117.70 (17)
C3—C4—C5	120.7 (2)	C13—C14—C15	104.93 (16)
C3—C4—H4	119.7	C8—C14—H14	106.9
C5—C4—H4	119.7	C13—C14—H14	106.9
C4—C5—C10	120.2 (2)	C15—C14—H14	106.9
C4—C5—C6	118.6 (2)	C16—C15—C14	105.10 (17)
C10—C5—C6	121.13 (19)	C16—C15—H15A	110.7
C5—C6—C7	112.43 (18)	C14—C15—H15A	110.7
C5—C6—H6A	109.1	C16—C15—H15B	110.7
C7—C6—H6A	109.1	C14—C15—H15B	110.7
C5—C6—H6B	109.1	H15A—C15—H15B	108.8
C7—C6—H6B	109.1	C15—C16—C17	106.14 (18)
H6A—C6—H6B	107.9	C15—C16—H16A	110.5
C6—C7—C8	111.26 (18)	C17—C16—H16A	110.5
C6—C7—H7A	109.4	C15—C16—H16B	110.5
C8—C7—H7A	109.4	C17—C16—H16B	110.5
C6—C7—H7B	109.4	H16A—C16—H16B	108.7
C8—C7—H7B	109.4	O2—C17—C21	108.75 (17)
H7A—C7—H7B	108.0	O2—C17—C16	109.0 (2)
C14—C8—C7	112.36 (16)	C21—C17—C16	110.2 (2)
C14—C8—C9	109.86 (15)	O2—C17—C13	114.86 (18)
C7—C8—C9	109.89 (17)	C21—C17—C13	111.54 (17)
C14—C8—H8	108.2	C16—C17—C13	102.34 (18)
C7—C8—H8	108.2	C13—C18—H18A	109.5
C9—C8—H8	108.2	C13—C18—H18B	109.5
C11—C9—C10	122.52 (17)	H18A—C18—H18B	109.5
C11—C9—C8	121.42 (17)	C13—C18—H18C	109.5
C10—C9—C8	116.03 (16)	H18A—C18—H18C	109.5
C1—C10—C5	117.21 (18)	H18B—C18—H18C	109.5
C1—C10—C9	121.55 (18)	O1—C20—H19A	109.5
C5—C10—C9	121.24 (17)	O1—C20—H19B	109.5
C9—C11—C12	126.00 (18)	H19A—C20—H19B	109.5
C9—C11—H11	117.0	O1—C20—H19C	109.5
C12—C11—H11	117.0	H19A—C20—H19C	109.5
C11—C12—C13	110.91 (15)	H19B—C20—H19C	109.5
C11—C12—H12A	109.5	C22—C21—C17	178.4 (2)
C13—C12—H12A	109.5	C21—C22—H21	180.0

C10—C1—C2—C3	1.2 (4)	C11—C12—C13—C14	45.3 (2)
C1—C2—C3—C4	−0.4 (4)	C11—C12—C13—C18	−77.5 (2)
C1—C2—C3—O1	177.2 (2)	C11—C12—C13—C17	158.11 (17)
C20—O1—C3—C4	−24.5 (3)	C7—C8—C14—C13	170.07 (16)
C20—O1—C3—C2	158.0 (2)	C9—C8—C14—C13	47.4 (2)
C2—C3—C4—C5	−0.2 (4)	C7—C8—C14—C15	−67.4 (2)
O1—C3—C4—C5	−177.6 (2)	C9—C8—C14—C15	169.92 (17)
C3—C4—C5—C10	0.0 (3)	C12—C13—C14—C8	−65.2 (2)
C3—C4—C5—C6	177.5 (2)	C18—C13—C14—C8	55.8 (2)
C4—C5—C6—C7	160.3 (2)	C17—C13—C14—C8	171.47 (15)
C10—C5—C6—C7	−22.3 (3)	C12—C13—C14—C15	165.44 (16)
C5—C6—C7—C8	50.9 (3)	C18—C13—C14—C15	−73.6 (2)
C6—C7—C8—C14	177.20 (18)	C17—C13—C14—C15	42.07 (18)
C6—C7—C8—C9	−60.2 (2)	C8—C14—C15—C16	−149.88 (18)
C14—C8—C9—C11	−13.5 (3)	C13—C14—C15—C16	−23.4 (2)
C7—C8—C9—C11	−137.59 (19)	C14—C15—C16—C17	−4.8 (2)
C14—C8—C9—C10	164.70 (15)	C15—C16—C17—O2	152.64 (18)
C7—C8—C9—C10	40.6 (2)	C15—C16—C17—C21	−88.1 (2)
C2—C1—C10—C5	−1.3 (3)	C15—C16—C17—C13	30.6 (2)
C2—C1—C10—C9	178.8 (2)	C12—C13—C17—O2	80.7 (2)
C4—C5—C10—C1	0.7 (3)	C14—C13—C17—O2	−162.21 (17)
C6—C5—C10—C1	−176.7 (2)	C18—C13—C17—O2	−43.9 (2)
C4—C5—C10—C9	−179.47 (17)	C12—C13—C17—C21	−43.6 (3)
C6—C5—C10—C9	3.1 (3)	C14—C13—C17—C21	73.5 (2)
C11—C9—C10—C1	−14.8 (3)	C18—C13—C17—C21	−168.21 (19)
C8—C9—C10—C1	167.05 (19)	C12—C13—C17—C16	−161.36 (18)
C11—C9—C10—C5	165.4 (2)	C14—C13—C17—C16	−44.3 (2)
C8—C9—C10—C5	−12.8 (3)	C18—C13—C17—C16	74.0 (2)
C10—C9—C11—C12	179.06 (17)	O2—C17—C21—C22	25 (10)
C8—C9—C11—C12	−2.9 (3)	C16—C17—C21—C22	−95 (10)
C9—C11—C12—C13	−14.1 (3)	C13—C17—C21—C22	152 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3···O1ⁱ	0.82 (4)	2.14 (4)	2.933 (3)	163 (3)

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄O₂
M_r	308.40
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.3773 (6), 10.7430 (9), 21.2555 (18)
V (Å³)	1684.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.43 × 0.35

Data collection
Diffractometer	Rigaku FCR CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.824, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9960, 2127, 1884
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.03
No. of reflections	2127
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3···O1ⁱ	0.82 (4)	2.14 (4)	2.933 (3)	163 (3)

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

Acknowledgements

Financial support of the project by the Program for Changjiang Scholars and Innovative Research Team in the University (No. IRT0526) and Shanghai Natural Science Foundation (No. 06ZR14001) is acknowledged.

References

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