supplementary materials


cv5384 scheme

Acta Cryst. (2013). E69, o635    [ doi:10.1107/S1600536813007290 ]

(Z)-3[beta]-(2-Chloroanilino)-17(20)-pregnene

J. Hu, J. Wang, Y. Xu, Y. Gao and G. Xiao

Abstract top

In the pregnene fragment of the title compound, C27H38ClN, the three six-membered rings exhibit chair conformations and the five-membered ring has a distorted envelope form with the fused C atom not bearing a methyl group as the flap atom. The amino group is involved in the formation of an intramolecular N-H...Cl hydrogen bond. The crystal packing exhibits no short intermolecular contacts.

Comment top

Pregnane-type steroidal alkaloids derivatives are used widely in medicine such as anti-cancer cell, anti-inflammatory and anti-HIV (Hua et al., 2005; Hunter et al., 2006). The goal of evaluating putative small molecule in anti-invasive and anti-metastatic of VEGF receptor selective antagonists has been of great interest in our group. Herewith, we report the synthesis and crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those reported for the related (Z)-3α-(1,3-dioxoisoindolin-2-yl)-17 (20)-pregnene (Qi et al., 2011). There are three cyclohexane rings (designated as rings A, B, and C from left to the right) and one cyclopentane ring (the D ring) in a steroid skeleton and hence there are three fusion points. Rings A/B, B/C and C/D all link as trans-trans -trans chair conformation. In the pregnene fragment, three six-membered rings exhibit the chair conformation, and a five-membered ring is in an envelope form. There is an ethenyl group attached to the five-membered ring and the angle of C17—C20—C21 between the ethenyl group and five-membered ring in the pregnane moiety is 129.41 (13)° which is deviated from the normal angle of sp2 hybridization because of the conformation. 3β-(2-chlorophenyl)amino group is bonded to the pregnene moiety. The 3β-(2-chlorophenyl)amino group is approximately planar, with an r.m.s. deviation 0.0113 (2) Å. The amino group is involved in formation of intramolecular N—H···Cl hydrogen bond (Table 1). The crystal packing exhibits no short intermolecular contacts.

Related literature top

For applications of pregnene-type steroidal alkaloid derivatives, see: Hua et al. (2005); Hunter & Priest (2006). For the crystal structure of the related compound (Z)-3α-(1,3-dioxoisoindolin-2-yl)-17 (20)-pregnene, see: Qi et al. (2011).

Experimental top

To a suspension of EtPPh3Br in anhydrous THF was added t-BuOK. A solution of commercially available epiandrosterone in THF was added. The resultant mixture was refluxed and stirred for 3 h to give pregn-17 (20)-en-3-ol in 50% yield. Steroid pregn-17 (20)-en-3-ol was dissolved in acetone and dichloromethane (1:1.5) then cooled to the temperature of 273 K. Jones reagent was added to give pregn-17 (20) -en-3-one in 55% yield. To a 10% solution of the carbonyl compound pregn-17 (20)-en-3-one in glacial acetic acid was added o-chloroaniline with stirring at the temperature of 288 K then sodium borohydride. Upon keeping the reaction mass at room temperature for 2 h afford the title compound (yield 70% after column chromatography purification). Crystals suitable for X-ray structure analysis were recrystalized from petroleum ether/ethyl acetate/dichloromethane (10:1:0.5) by slow evaporation of the solvent at room temperature after several days.

Refinement top

H atom of the amino group was located in a difference map and isotropically refined. Other H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq or 1.5Ueq (parent).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 55% probability level. Dashed line denotes an intramolecular hydrogen bond.
(Z)-3β-(2-Chloroanilino)-17 (20)-pregnene top
Crystal data top
C27H38ClNF(000) = 448
Mr = 412.03Dx = 1.229 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4165 reflections
a = 7.281 (1) Åθ = 1.2–27.9°
b = 17.467 (2) ŵ = 0.19 mm1
c = 9.1310 (12) ÅT = 113 K
β = 106.447 (7)°Prism, colourless
V = 1113.7 (2) Å30.26 × 0.24 × 0.18 mm
Z = 2
Data collection top
Rigaku Saturn724 CCD
diffractometer
5276 independent reflections
Radiation source: rotating anode4089 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.038
Detector resolution: 14.222 pixels mm-1θmax = 27.9°, θmin = 2.3°
ω scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2222
Tmin = 0.953, Tmax = 0.967l = 1111
14303 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.0299P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
5276 reflectionsΔρmax = 0.18 e Å3
269 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 2537 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (3)
Crystal data top
C27H38ClNV = 1113.7 (2) Å3
Mr = 412.03Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.281 (1) ŵ = 0.19 mm1
b = 17.467 (2) ÅT = 113 K
c = 9.1310 (12) Å0.26 × 0.24 × 0.18 mm
β = 106.447 (7)°
Data collection top
Rigaku Saturn724 CCD
diffractometer
5276 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
4089 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.967Rint = 0.038
14303 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066Δρmax = 0.18 e Å3
S = 0.97Δρmin = 0.25 e Å3
5276 reflectionsAbsolute structure: Flack (1983), 2537 Friedel pairs
269 parametersFlack parameter: 0.02 (3)
1 restraint
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
Cl10.65026 (5)0.47549 (2)0.27405 (4)0.02681 (9)
N10.72923 (18)0.63876 (7)0.23132 (14)0.0219 (3)
C10.4738 (2)0.83125 (8)0.15203 (16)0.0184 (3)
H1A0.34080.84340.15150.022*
H1B0.48850.84570.05110.022*
C1'0.86537 (19)0.59002 (8)0.20670 (15)0.0179 (3)
C20.50533 (19)0.74475 (8)0.17404 (17)0.0193 (3)
H2A0.42140.71790.08430.023*
H2B0.46690.72860.26500.023*
C2'0.84853 (19)0.51050 (8)0.22294 (15)0.0188 (3)
C30.7134 (2)0.72010 (8)0.19420 (16)0.0194 (3)
H30.74210.72720.09430.023*
C3'0.9773 (2)0.45928 (8)0.19481 (17)0.0235 (3)
H3'0.95930.40600.20640.028*
C40.8522 (2)0.76977 (8)0.31296 (16)0.0193 (3)
H4A0.83700.75860.41520.023*
H4B0.98520.75670.31490.023*
C4'1.1333 (2)0.48461 (9)0.14969 (15)0.0260 (3)
H4'1.22280.44930.13020.031*
C50.81801 (19)0.85484 (8)0.27867 (16)0.0168 (3)
H50.82930.86310.17320.020*
C5'1.1556 (2)0.56290 (9)0.13369 (16)0.0253 (3)
H5'1.26170.58130.10290.030*
C60.97282 (19)0.90405 (8)0.38521 (17)0.0213 (3)
H6A0.96900.89660.49180.026*
H6B1.10020.88740.37860.026*
C6'1.0254 (2)0.61462 (8)0.16199 (16)0.0218 (3)
H6'1.04460.66790.15100.026*
C70.94543 (18)0.98860 (8)0.34445 (16)0.0203 (3)
H7A0.96520.99710.24280.024*
H7B1.04251.01890.42000.024*
C80.74540 (18)1.01621 (7)0.34212 (16)0.0156 (3)
H80.73121.01160.44760.019*
C90.58989 (18)0.96592 (8)0.23272 (15)0.0147 (3)
H90.61200.97030.12980.018*
C100.61220 (18)0.87966 (8)0.27571 (15)0.0151 (3)
C110.38697 (19)0.99738 (7)0.21507 (16)0.0197 (3)
H11A0.29530.96880.13230.024*
H11B0.35270.98750.31080.024*
C120.36389 (19)1.08327 (8)0.17908 (17)0.0192 (3)
H12A0.37581.09250.07520.023*
H12B0.23441.09980.18050.023*
C130.51445 (19)1.13112 (7)0.29440 (15)0.0151 (3)
C140.71243 (18)1.09903 (8)0.29169 (16)0.0157 (3)
H140.71301.10010.18230.019*
C150.85384 (19)1.16029 (8)0.37215 (16)0.0213 (3)
H15A0.97811.15490.34910.026*
H15B0.87541.15860.48410.026*
C160.7503 (2)1.23417 (8)0.30321 (18)0.0241 (3)
H16A0.78321.27660.37800.029*
H16B0.78701.24910.21070.029*
C170.5354 (2)1.21616 (8)0.26260 (15)0.0171 (3)
C180.4833 (2)1.12587 (8)0.45464 (16)0.0217 (3)
H18A0.58951.15120.52930.026*
H18B0.47791.07200.48290.026*
H18C0.36261.15110.45340.026*
C190.57245 (19)0.86552 (8)0.43077 (15)0.0199 (3)
H19A0.58880.81100.45650.024*
H19B0.44100.88100.42420.024*
H19C0.66230.89560.51010.024*
C200.4035 (2)1.27000 (8)0.22004 (15)0.0198 (3)
H200.45071.31980.20920.024*
C210.18870 (19)1.26393 (8)0.18609 (17)0.0228 (3)
H21A0.15101.20990.17590.027*
H21B0.12741.29090.09060.027*
H21C0.14831.28710.26970.027*
H100.635 (3)0.6182 (12)0.259 (2)0.059 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02351 (18)0.01886 (16)0.0400 (2)0.00103 (17)0.01213 (15)0.00106 (17)
N10.0254 (7)0.0144 (6)0.0291 (7)0.0032 (5)0.0132 (6)0.0030 (5)
C10.0165 (7)0.0165 (7)0.0206 (8)0.0016 (6)0.0030 (6)0.0003 (6)
C1'0.0200 (7)0.0189 (7)0.0130 (7)0.0026 (6)0.0020 (5)0.0013 (6)
C20.0190 (7)0.0168 (7)0.0206 (8)0.0010 (6)0.0032 (6)0.0004 (6)
C2'0.0175 (7)0.0200 (7)0.0180 (7)0.0008 (6)0.0037 (6)0.0003 (6)
C30.0234 (7)0.0140 (7)0.0211 (8)0.0022 (6)0.0070 (6)0.0027 (6)
C3'0.0263 (8)0.0176 (8)0.0239 (8)0.0050 (6)0.0026 (6)0.0016 (6)
C40.0181 (7)0.0168 (7)0.0235 (8)0.0047 (6)0.0066 (6)0.0019 (6)
C4'0.0240 (7)0.0274 (9)0.0268 (8)0.0092 (7)0.0076 (6)0.0013 (7)
C50.0152 (7)0.0182 (7)0.0176 (7)0.0025 (5)0.0056 (6)0.0010 (6)
C5'0.0223 (8)0.0320 (9)0.0232 (8)0.0016 (6)0.0088 (6)0.0020 (6)
C60.0131 (7)0.0214 (8)0.0277 (8)0.0029 (6)0.0030 (6)0.0004 (6)
C6'0.0240 (8)0.0175 (8)0.0241 (8)0.0002 (6)0.0069 (6)0.0015 (6)
C70.0130 (6)0.0196 (9)0.0265 (8)0.0002 (5)0.0029 (6)0.0003 (6)
C80.0129 (7)0.0156 (7)0.0177 (7)0.0003 (5)0.0033 (5)0.0009 (5)
C90.0141 (6)0.0152 (7)0.0146 (7)0.0014 (6)0.0039 (5)0.0003 (5)
C100.0123 (6)0.0161 (7)0.0165 (7)0.0007 (5)0.0033 (5)0.0006 (6)
C110.0136 (7)0.0165 (8)0.0260 (8)0.0003 (5)0.0008 (6)0.0006 (6)
C120.0140 (7)0.0159 (7)0.0253 (8)0.0012 (5)0.0018 (6)0.0010 (6)
C130.0147 (7)0.0144 (7)0.0159 (7)0.0009 (5)0.0039 (5)0.0009 (5)
C140.0139 (7)0.0186 (7)0.0154 (7)0.0006 (6)0.0054 (5)0.0014 (5)
C150.0150 (7)0.0203 (8)0.0282 (8)0.0018 (6)0.0052 (6)0.0004 (6)
C160.0188 (8)0.0202 (8)0.0313 (9)0.0017 (6)0.0036 (6)0.0007 (6)
C170.0198 (7)0.0168 (7)0.0143 (7)0.0019 (6)0.0043 (6)0.0032 (6)
C180.0231 (7)0.0209 (7)0.0239 (8)0.0033 (6)0.0114 (6)0.0004 (6)
C190.0187 (7)0.0203 (7)0.0222 (8)0.0029 (6)0.0081 (6)0.0022 (6)
C200.0236 (7)0.0164 (7)0.0207 (7)0.0002 (6)0.0083 (6)0.0006 (6)
C210.0249 (8)0.0184 (8)0.0266 (8)0.0032 (6)0.0099 (6)0.0002 (6)
Geometric parameters (Å, º) top
Cl1—C2'1.7485 (14)C8—C91.5527 (18)
N1—C1'1.3726 (18)C8—H81.0000
N1—C31.4576 (17)C9—C111.5414 (17)
N1—H100.875 (19)C9—C101.554 (2)
C1—C21.5329 (18)C9—H91.0000
C1—C101.5367 (18)C10—C191.5432 (18)
C1—H1A0.9900C11—C121.5349 (18)
C1—H1B0.9900C11—H11A0.9900
C1'—C2'1.4060 (19)C11—H11B0.9900
C1'—C6'1.4064 (19)C12—C131.5347 (19)
C2—C31.5350 (18)C12—H12A0.9900
C2—H2A0.9900C12—H12B0.9900
C2—H2B0.9900C13—C171.5295 (19)
C2'—C3'1.3715 (18)C13—C181.5456 (18)
C3—C41.5263 (19)C13—C141.5533 (18)
C3—H31.0000C14—C151.5219 (19)
C3'—C4'1.386 (2)C14—H141.0000
C3'—H3'0.9500C15—C161.537 (2)
C4—C51.5244 (19)C15—H15A0.9900
C4—H4A0.9900C15—H15B0.9900
C4—H4B0.9900C16—C171.5355 (19)
C4'—C5'1.390 (2)C16—H16A0.9900
C4'—H4'0.9500C16—H16B0.9900
C5—C61.5280 (19)C17—C201.3215 (19)
C5—C101.5528 (18)C18—H18A0.9800
C5—H51.0000C18—H18B0.9800
C5'—C6'1.386 (2)C18—H18C0.9800
C5'—H5'0.9500C19—H19A0.9800
C6—C71.5222 (19)C19—H19B0.9800
C6—H6A0.9900C19—H19C0.9800
C6—H6B0.9900C20—C211.5092 (19)
C6'—H6'0.9500C20—H200.9500
C7—C81.5286 (18)C21—H21A0.9800
C7—H7A0.9900C21—H21B0.9800
C7—H7B0.9900C21—H21C0.9800
C8—C141.5166 (18)
C1'—N1—C3125.43 (13)C8—C9—C10112.39 (10)
C1'—N1—H10117.1 (14)C11—C9—H9106.2
C3—N1—H10116.8 (14)C8—C9—H9106.2
C2—C1—C10113.79 (11)C10—C9—H9106.2
C2—C1—H1A108.8C1—C10—C19109.39 (11)
C10—C1—H1A108.8C1—C10—C5106.74 (11)
C2—C1—H1B108.8C19—C10—C5111.72 (10)
C10—C1—H1B108.8C1—C10—C9110.37 (10)
H1A—C1—H1B107.7C19—C10—C9110.70 (11)
N1—C1'—C2'120.46 (13)C5—C10—C9107.84 (10)
N1—C1'—C6'123.65 (13)C12—C11—C9114.48 (11)
C2'—C1'—C6'115.88 (12)C12—C11—H11A108.6
C1—C2—C3113.46 (11)C9—C11—H11A108.6
C1—C2—H2A108.9C12—C11—H11B108.6
C3—C2—H2A108.9C9—C11—H11B108.6
C1—C2—H2B108.9H11A—C11—H11B107.6
C3—C2—H2B108.9C13—C12—C11111.82 (11)
H2A—C2—H2B107.7C13—C12—H12A109.3
C3'—C2'—C1'122.68 (13)C11—C12—H12A109.3
C3'—C2'—Cl1118.79 (11)C13—C12—H12B109.3
C1'—C2'—Cl1118.48 (10)C11—C12—H12B109.3
N1—C3—C4113.32 (11)H12A—C12—H12B107.9
N1—C3—C2108.16 (11)C17—C13—C12119.26 (12)
C4—C3—C2111.01 (11)C17—C13—C18106.65 (11)
N1—C3—H3108.1C12—C13—C18110.45 (12)
C4—C3—H3108.1C17—C13—C14101.81 (11)
C2—C3—H3108.1C12—C13—C14106.17 (11)
C2'—C3'—C4'120.58 (13)C18—C13—C14112.30 (11)
C2'—C3'—H3'119.7C8—C14—C15119.79 (11)
C4'—C3'—H3'119.7C8—C14—C13114.02 (11)
C5—C4—C3111.79 (11)C15—C14—C13104.05 (11)
C5—C4—H4A109.3C8—C14—H14106.0
C3—C4—H4A109.3C15—C14—H14106.0
C5—C4—H4B109.3C13—C14—H14106.0
C3—C4—H4B109.3C14—C15—C16101.91 (11)
H4A—C4—H4B107.9C14—C15—H15A111.4
C3'—C4'—C5'118.37 (14)C16—C15—H15A111.4
C3'—C4'—H4'120.8C14—C15—H15B111.4
C5'—C4'—H4'120.8C16—C15—H15B111.4
C4—C5—C6111.68 (11)H15A—C15—H15B109.3
C4—C5—C10112.12 (11)C17—C16—C15105.97 (11)
C6—C5—C10112.85 (11)C17—C16—H16A110.5
C4—C5—H5106.6C15—C16—H16A110.5
C6—C5—H5106.6C17—C16—H16B110.5
C10—C5—H5106.6C15—C16—H16B110.5
C6'—C5'—C4'121.03 (14)H16A—C16—H16B108.7
C6'—C5'—H5'119.5C20—C17—C13130.08 (13)
C4'—C5'—H5'119.5C20—C17—C16122.11 (13)
C7—C6—C5111.61 (11)C13—C17—C16107.61 (11)
C7—C6—H6A109.3C13—C18—H18A109.5
C5—C6—H6A109.3C13—C18—H18B109.5
C7—C6—H6B109.3H18A—C18—H18B109.5
C5—C6—H6B109.3C13—C18—H18C109.5
H6A—C6—H6B108.0H18A—C18—H18C109.5
C5'—C6'—C1'121.45 (14)H18B—C18—H18C109.5
C5'—C6'—H6'119.3C10—C19—H19A109.5
C1'—C6'—H6'119.3C10—C19—H19B109.5
C6—C7—C8111.58 (11)H19A—C19—H19B109.5
C6—C7—H7A109.3C10—C19—H19C109.5
C8—C7—H7A109.3H19A—C19—H19C109.5
C6—C7—H7B109.3H19B—C19—H19C109.5
C8—C7—H7B109.3C17—C20—C21129.41 (13)
H7A—C7—H7B108.0C17—C20—H20115.3
C14—C8—C7111.92 (11)C21—C20—H20115.3
C14—C8—C9108.69 (11)C20—C21—H21A109.5
C7—C8—C9110.42 (11)C20—C21—H21B109.5
C14—C8—H8108.6H21A—C21—H21B109.5
C7—C8—H8108.6C20—C21—H21C109.5
C9—C8—H8108.6H21A—C21—H21C109.5
C11—C9—C8111.62 (11)H21B—C21—H21C109.5
C11—C9—C10113.61 (10)
C3—N1—C1'—C2'169.28 (13)C4—C5—C10—C9177.45 (11)
C3—N1—C1'—C6'9.5 (2)C6—C5—C10—C955.39 (14)
C10—C1—C2—C352.24 (16)C11—C9—C10—C159.98 (14)
N1—C1'—C2'—C3'177.82 (13)C8—C9—C10—C1172.07 (10)
C6'—C1'—C2'—C3'1.1 (2)C11—C9—C10—C1961.28 (13)
N1—C1'—C2'—Cl10.32 (18)C8—C9—C10—C1966.67 (13)
C6'—C1'—C2'—Cl1178.57 (10)C11—C9—C10—C5176.22 (11)
C1'—N1—C3—C480.43 (17)C8—C9—C10—C555.83 (13)
C1'—N1—C3—C2156.05 (13)C8—C9—C11—C1249.27 (15)
C1—C2—C3—N1173.59 (11)C10—C9—C11—C12177.62 (11)
C1—C2—C3—C448.69 (16)C9—C11—C12—C1352.96 (16)
C1'—C2'—C3'—C4'0.6 (2)C11—C12—C13—C17170.00 (11)
Cl1—C2'—C3'—C4'178.12 (11)C11—C12—C13—C1865.98 (15)
N1—C3—C4—C5174.30 (11)C11—C12—C13—C1456.00 (15)
C2—C3—C4—C552.36 (16)C7—C8—C14—C1553.21 (16)
C2'—C3'—C4'—C5'0.1 (2)C9—C8—C14—C15175.43 (11)
C3—C4—C5—C6172.62 (11)C7—C8—C14—C13177.36 (11)
C3—C4—C5—C1059.60 (15)C9—C8—C14—C1360.42 (14)
C3'—C4'—C5'—C6'0.0 (2)C17—C13—C14—C8171.90 (11)
C4—C5—C6—C7176.45 (11)C12—C13—C14—C862.61 (14)
C10—C5—C6—C756.16 (15)C18—C13—C14—C858.19 (15)
C4'—C5'—C6'—C1'0.5 (2)C17—C13—C14—C1539.67 (13)
N1—C1'—C6'—C5'177.85 (13)C12—C13—C14—C15165.16 (11)
C2'—C1'—C6'—C5'1.0 (2)C18—C13—C14—C1574.04 (14)
C5—C6—C7—C855.07 (16)C8—C14—C15—C16171.63 (12)
C6—C7—C8—C14176.32 (11)C13—C14—C15—C1642.82 (13)
C6—C7—C8—C955.10 (15)C14—C15—C16—C1729.17 (15)
C14—C8—C9—C1150.99 (14)C12—C13—C17—C2047.9 (2)
C7—C8—C9—C11174.11 (11)C18—C13—C17—C2077.94 (18)
C14—C8—C9—C10179.98 (10)C14—C13—C17—C20164.22 (14)
C7—C8—C9—C1056.89 (14)C12—C13—C17—C16137.25 (13)
C2—C1—C10—C1965.95 (15)C18—C13—C17—C1696.90 (13)
C2—C1—C10—C555.09 (14)C14—C13—C17—C1620.94 (14)
C2—C1—C10—C9172.02 (11)C15—C16—C17—C20170.51 (13)
C4—C5—C10—C158.86 (13)C15—C16—C17—C134.83 (16)
C6—C5—C10—C1173.99 (11)C13—C17—C20—C211.4 (2)
C4—C5—C10—C1960.68 (15)C16—C17—C20—C21175.62 (14)
C6—C5—C10—C1966.48 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H10···Cl10.875 (19)2.50 (2)2.9569 (13)113.5 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H10···Cl10.875 (19)2.50 (2)2.9569 (13)113.5 (16)
Acknowledgements top

This project was supported by the Science and Technology Department of Liaoning Province Science Foundation (grant No. 2010226003), Graduate Education Innovation Program 2010.

references
References top

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Hua, Z. H., Carcache, D. A., Tian, Y., Li, Y.-M. & Danishiefsky, S. J. (2005). J. Org. Chem. 702, 9849–9856.

Hunter, A. C. & Priest, S.-M. (2006). Steroids, 71, 30–33.

Qi, Y., Qin, N. & Duan, H.-Q. (2011). Acta Cryst. E67, o2065.

Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.