organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Doussot, J., Garreau, R., Dallery, L., Guette, J.-P. & Guy, A. (1995). Bull. Soc. Chim. Fr. 132, 59-66.]); Ekhato et al. (2002[Ekhato, I. V., Hurley, T., Lovdahl, M., Revitte, T. J., Guo, L., Huang, Y., Clipper, S. & Colson, C. (2002). Steroids, 67, 165-174.]); Sedee et al. (1985[Sedee, A. G. J., van Henegouwen, G. M. J. B., de Vries, M. E. & Erkelens, C. (1985). Steroids, 45, 101-118.]); Steiner et al. (1997[Steiner, T., Lutz, B., van der Maas, J., Veldman, N., Schreurs, A. M. M., Kroon, J. & Kanters, J. A. (1997). Chem. Commun. pp. 191-192.]).

[Scheme 1]

Experimental

Crystal data
  • C21H24O2

  • Mr = 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.824, Tmax = 1.000 (expected range = 0.802–0.974)

  • 9960 measured reflections

  • 2127 independent reflections

  • 1884 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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).

Refinement top

The H atom bonded to O was located in a difference map and refined with a distance restraint of O—H = 0.82 (4) Å. Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for benzene and acetylenic C—H, 0.96 Å for methyl C—H, 0.97 Å for methylene C—H, and 0.98Å for methine C—H; Uiso(H) = 1.2Ueq(C) except for methyl groups, where Uiso(H) = 1.5Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged.

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
[Figure 1] 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.
[Figure 2] 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
C21H24O2Dx = 1.216 Mg m3
Mr = 308.40Melting point: 145 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 7.3773 (6) ÅCell parameters from 3971 reflections
b = 10.7430 (9) Åθ = 5.4–53.4°
c = 21.2555 (18) ŵ = 0.08 mm1
V = 1684.6 (2) Å3T = 293 K
Z = 4Prismatic, colorless
F(000) = 6640.50 × 0.43 × 0.35 mm
Data collection top
Rigaku FCR CCD area-detector
diffractometer
2127 independent reflections
Radiation source: fine-focus sealed tube1884 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ϕ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 79
Tmin = 0.824, Tmax = 1.000k = 139
9960 measured reflectionsl = 2527
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0757P)2 + 0.0067P]
where P = (Fo2 + 2Fc2)/3
2127 reflections(Δ/σ)max = 0.001
214 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C21H24O2V = 1684.6 (2) Å3
Mr = 308.40Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.3773 (6) ŵ = 0.08 mm1
b = 10.7430 (9) ÅT = 293 K
c = 21.2555 (18) Å0.50 × 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)
Tmin = 0.824, Tmax = 1.000Rint = 0.071
9960 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.20 e Å3
2127 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
O10.3222 (3)0.77612 (18)0.73106 (7)0.0684 (5)
O20.5307 (3)0.26039 (16)1.17027 (8)0.0583 (5)
C10.2555 (3)0.6031 (2)0.87459 (10)0.0502 (5)
H10.16180.55840.89320.060*
C20.2245 (3)0.6607 (2)0.81810 (10)0.0556 (6)
H20.11080.65610.79940.067*
C30.3626 (3)0.7256 (2)0.78916 (10)0.0497 (5)
C40.5296 (3)0.7326 (2)0.81737 (10)0.0503 (5)
H40.62270.77620.79780.060*
C50.5612 (3)0.67502 (19)0.87522 (10)0.0422 (5)
C60.7485 (3)0.6809 (2)0.90286 (11)0.0548 (6)
H6A0.79930.76280.89510.066*
H6B0.82500.62030.88200.066*
C70.7495 (3)0.6558 (2)0.97282 (11)0.0496 (5)
H7A0.69360.72510.99470.059*
H7B0.87370.64870.98730.059*
C80.6478 (2)0.53696 (19)0.98837 (9)0.0362 (4)
H80.70430.46840.96520.043*
C90.4518 (3)0.54791 (17)0.96698 (9)0.0345 (4)
C100.4221 (3)0.60908 (18)0.90521 (9)0.0380 (4)
C110.3154 (3)0.50772 (19)1.00285 (9)0.0376 (4)
H110.19850.52070.98780.045*
C120.3331 (3)0.44369 (19)1.06504 (9)0.0379 (4)
H12A0.25220.37261.06630.045*
H12B0.29800.50041.09840.045*
C130.5267 (3)0.40034 (17)1.07587 (8)0.0358 (4)
C140.6545 (3)0.50617 (18)1.05775 (9)0.0369 (4)
H140.61330.58041.08040.044*
C150.8389 (3)0.4696 (2)1.08594 (10)0.0517 (6)
H15A0.91400.42881.05470.062*
H15B0.90230.54241.10150.062*
C160.7939 (3)0.3803 (3)1.13995 (11)0.0572 (6)
H16A0.84670.40971.17900.069*
H16B0.84080.29781.13110.069*
C170.5855 (3)0.3774 (2)1.14476 (10)0.0447 (5)
C180.5615 (3)0.28188 (19)1.03758 (9)0.0471 (5)
H18A0.52950.29620.99440.071*
H18B0.48930.21511.05410.071*
H18C0.68740.26011.04020.071*
C200.4291 (5)0.8770 (3)0.70975 (14)0.0782 (9)
H19A0.55120.84930.70300.117*
H19B0.42840.94190.74080.117*
H19C0.38010.90830.67100.117*
C210.5210 (3)0.4781 (2)1.18698 (9)0.0500 (5)
C220.4707 (4)0.5547 (3)1.22112 (11)0.0644 (7)
H210.43030.61621.24850.077*
H30.425 (5)0.260 (3)1.1812 (13)0.079 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0730 (12)0.0800 (12)0.0523 (9)0.0059 (10)0.0010 (9)0.0254 (8)
O20.0669 (13)0.0551 (10)0.0528 (9)0.0104 (9)0.0036 (8)0.0111 (7)
C10.0378 (11)0.0683 (14)0.0445 (11)0.0046 (11)0.0001 (9)0.0071 (10)
C20.0426 (12)0.0772 (16)0.0472 (12)0.0009 (12)0.0074 (9)0.0103 (12)
C30.0527 (12)0.0535 (12)0.0429 (11)0.0087 (11)0.0024 (9)0.0062 (10)
C40.0492 (13)0.0485 (12)0.0532 (12)0.0034 (10)0.0119 (10)0.0080 (10)
C50.0393 (11)0.0396 (10)0.0477 (11)0.0016 (8)0.0050 (9)0.0006 (9)
C60.0379 (11)0.0630 (14)0.0634 (14)0.0149 (11)0.0014 (10)0.0112 (12)
C70.0365 (10)0.0542 (12)0.0580 (13)0.0110 (10)0.0068 (9)0.0003 (10)
C80.0274 (8)0.0414 (10)0.0396 (10)0.0003 (8)0.0002 (7)0.0059 (8)
C90.0311 (9)0.0332 (9)0.0392 (9)0.0010 (8)0.0021 (7)0.0051 (7)
C100.0350 (10)0.0392 (10)0.0399 (9)0.0004 (8)0.0028 (8)0.0037 (8)
C110.0276 (8)0.0424 (10)0.0429 (10)0.0019 (8)0.0013 (8)0.0005 (8)
C120.0321 (10)0.0410 (10)0.0406 (10)0.0013 (8)0.0003 (8)0.0013 (8)
C130.0342 (9)0.0373 (9)0.0358 (9)0.0037 (8)0.0004 (7)0.0044 (7)
C140.0301 (9)0.0410 (10)0.0397 (9)0.0024 (8)0.0031 (7)0.0086 (8)
C150.0348 (11)0.0690 (15)0.0515 (12)0.0035 (11)0.0083 (9)0.0047 (11)
C160.0463 (12)0.0728 (16)0.0525 (13)0.0130 (12)0.0124 (10)0.0021 (11)
C170.0474 (11)0.0477 (11)0.0390 (10)0.0075 (10)0.0031 (8)0.0003 (9)
C180.0522 (12)0.0395 (10)0.0496 (11)0.0024 (10)0.0042 (10)0.0091 (9)
C200.101 (2)0.0648 (16)0.0685 (16)0.0106 (18)0.0222 (16)0.0199 (13)
C210.0557 (13)0.0572 (13)0.0369 (10)0.0028 (11)0.0062 (9)0.0045 (10)
C220.0740 (17)0.0709 (16)0.0482 (12)0.0020 (15)0.0018 (12)0.0185 (12)
Geometric parameters (Å, º) top
O1—C31.381 (3)C11—C121.496 (3)
O1—C201.415 (4)C11—H110.9300
O2—C171.428 (3)C12—C131.520 (3)
O2—H30.82 (4)C12—H12A0.9700
C1—C21.370 (3)C12—H12B0.9700
C1—C101.392 (3)C13—C141.526 (3)
C1—H10.9300C13—C181.532 (3)
C2—C31.379 (3)C13—C171.547 (3)
C2—H20.9300C14—C151.538 (3)
C3—C41.373 (3)C14—H140.9800
C4—C51.396 (3)C15—C161.532 (3)
C4—H40.9300C15—H15A0.9700
C5—C101.400 (3)C15—H15B0.9700
C5—C61.503 (3)C16—C171.542 (3)
C6—C71.511 (3)C16—H16A0.9700
C6—H6A0.9700C16—H16B0.9700
C6—H6B0.9700C17—C211.483 (3)
C7—C81.517 (3)C18—H18A0.9600
C7—H7A0.9700C18—H18B0.9600
C7—H7B0.9700C18—H18C0.9600
C8—C141.512 (3)C20—H19A0.9600
C8—C91.520 (2)C20—H19B0.9600
C8—H80.9800C20—H19C0.9600
C9—C111.334 (3)C21—C221.159 (3)
C9—C101.484 (3)C22—H210.9300
C3—O1—C20117.8 (2)C11—C12—H12B109.5
C17—O2—H3113 (2)C13—C12—H12B109.5
C2—C1—C10122.4 (2)H12A—C12—H12B108.0
C2—C1—H1118.8C12—C13—C14108.29 (15)
C10—C1—H1118.8C12—C13—C18109.35 (17)
C1—C2—C3119.7 (2)C14—C13—C18112.42 (16)
C1—C2—H2120.1C12—C13—C17117.09 (16)
C3—C2—H2120.1C14—C13—C17100.62 (15)
C4—C3—C2119.7 (2)C18—C13—C17108.90 (16)
C4—C3—O1124.2 (2)C8—C14—C13112.88 (15)
C2—C3—O1116.0 (2)C8—C14—C15117.70 (17)
C3—C4—C5120.7 (2)C13—C14—C15104.93 (16)
C3—C4—H4119.7C8—C14—H14106.9
C5—C4—H4119.7C13—C14—H14106.9
C4—C5—C10120.2 (2)C15—C14—H14106.9
C4—C5—C6118.6 (2)C16—C15—C14105.10 (17)
C10—C5—C6121.13 (19)C16—C15—H15A110.7
C5—C6—C7112.43 (18)C14—C15—H15A110.7
C5—C6—H6A109.1C16—C15—H15B110.7
C7—C6—H6A109.1C14—C15—H15B110.7
C5—C6—H6B109.1H15A—C15—H15B108.8
C7—C6—H6B109.1C15—C16—C17106.14 (18)
H6A—C6—H6B107.9C15—C16—H16A110.5
C6—C7—C8111.26 (18)C17—C16—H16A110.5
C6—C7—H7A109.4C15—C16—H16B110.5
C8—C7—H7A109.4C17—C16—H16B110.5
C6—C7—H7B109.4H16A—C16—H16B108.7
C8—C7—H7B109.4O2—C17—C21108.75 (17)
H7A—C7—H7B108.0O2—C17—C16109.0 (2)
C14—C8—C7112.36 (16)C21—C17—C16110.2 (2)
C14—C8—C9109.86 (15)O2—C17—C13114.86 (18)
C7—C8—C9109.89 (17)C21—C17—C13111.54 (17)
C14—C8—H8108.2C16—C17—C13102.34 (18)
C7—C8—H8108.2C13—C18—H18A109.5
C9—C8—H8108.2C13—C18—H18B109.5
C11—C9—C10122.52 (17)H18A—C18—H18B109.5
C11—C9—C8121.42 (17)C13—C18—H18C109.5
C10—C9—C8116.03 (16)H18A—C18—H18C109.5
C1—C10—C5117.21 (18)H18B—C18—H18C109.5
C1—C10—C9121.55 (18)O1—C20—H19A109.5
C5—C10—C9121.24 (17)O1—C20—H19B109.5
C9—C11—C12126.00 (18)H19A—C20—H19B109.5
C9—C11—H11117.0O1—C20—H19C109.5
C12—C11—H11117.0H19A—C20—H19C109.5
C11—C12—C13110.91 (15)H19B—C20—H19C109.5
C11—C12—H12A109.5C22—C21—C17178.4 (2)
C13—C12—H12A109.5C21—C22—H21180.0
C10—C1—C2—C31.2 (4)C11—C12—C13—C1445.3 (2)
C1—C2—C3—C40.4 (4)C11—C12—C13—C1877.5 (2)
C1—C2—C3—O1177.2 (2)C11—C12—C13—C17158.11 (17)
C20—O1—C3—C424.5 (3)C7—C8—C14—C13170.07 (16)
C20—O1—C3—C2158.0 (2)C9—C8—C14—C1347.4 (2)
C2—C3—C4—C50.2 (4)C7—C8—C14—C1567.4 (2)
O1—C3—C4—C5177.6 (2)C9—C8—C14—C15169.92 (17)
C3—C4—C5—C100.0 (3)C12—C13—C14—C865.2 (2)
C3—C4—C5—C6177.5 (2)C18—C13—C14—C855.8 (2)
C4—C5—C6—C7160.3 (2)C17—C13—C14—C8171.47 (15)
C10—C5—C6—C722.3 (3)C12—C13—C14—C15165.44 (16)
C5—C6—C7—C850.9 (3)C18—C13—C14—C1573.6 (2)
C6—C7—C8—C14177.20 (18)C17—C13—C14—C1542.07 (18)
C6—C7—C8—C960.2 (2)C8—C14—C15—C16149.88 (18)
C14—C8—C9—C1113.5 (3)C13—C14—C15—C1623.4 (2)
C7—C8—C9—C11137.59 (19)C14—C15—C16—C174.8 (2)
C14—C8—C9—C10164.70 (15)C15—C16—C17—O2152.64 (18)
C7—C8—C9—C1040.6 (2)C15—C16—C17—C2188.1 (2)
C2—C1—C10—C51.3 (3)C15—C16—C17—C1330.6 (2)
C2—C1—C10—C9178.8 (2)C12—C13—C17—O280.7 (2)
C4—C5—C10—C10.7 (3)C14—C13—C17—O2162.21 (17)
C6—C5—C10—C1176.7 (2)C18—C13—C17—O243.9 (2)
C4—C5—C10—C9179.47 (17)C12—C13—C17—C2143.6 (3)
C6—C5—C10—C93.1 (3)C14—C13—C17—C2173.5 (2)
C11—C9—C10—C114.8 (3)C18—C13—C17—C21168.21 (19)
C8—C9—C10—C1167.05 (19)C12—C13—C17—C16161.36 (18)
C11—C9—C10—C5165.4 (2)C14—C13—C17—C1644.3 (2)
C8—C9—C10—C512.8 (3)C18—C13—C17—C1674.0 (2)
C10—C9—C11—C12179.06 (17)O2—C17—C21—C2225 (10)
C8—C9—C11—C122.9 (3)C16—C17—C21—C2295 (10)
C9—C11—C12—C1314.1 (3)C13—C17—C21—C22152 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H3···O1i0.82 (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 formulaC21H24O2
Mr308.40
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.3773 (6), 10.7430 (9), 21.2555 (18)
V3)1684.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.43 × 0.35
Data collection
DiffractometerRigaku FCR CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.824, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
9960, 2127, 1884
Rint0.071
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.114, 1.03
No. of reflections2127
No. of parameters214
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.24

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H3···O1i0.82 (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

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDoussot, J., Garreau, R., Dallery, L., Guette, J.-P. & Guy, A. (1995). Bull. Soc. Chim. Fr. 132, 59–66.  CAS Google Scholar
First citationEkhato, I. V., Hurley, T., Lovdahl, M., Revitte, T. J., Guo, L., Huang, Y., Clipper, S. & Colson, C. (2002). Steroids, 67, 165–174.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSedee, A. G. J., van Henegouwen, G. M. J. B., de Vries, M. E. & Erkelens, C. (1985). Steroids, 45, 101–118.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSteiner, T., Lutz, B., van der Maas, J., Veldman, N., Schreurs, A. M. M., Kroon, J. & Kanters, J. A. (1997). Chem. Commun. pp. 191–192.  CSD CrossRef Web of Science Google Scholar

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