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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1125.
Published online 2009 April 25. doi:  10.1107/S1600536809014597
PMCID: PMC2981155

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

Abstract

In the title steroid derivative, C23H37IO, the fused cyclo­propane unit that comprises part of the A ring has a β-configuration, and the associated cyclo­pentane ring has an envelope conformation.

Related literature

This iodo-substituted steroid was synthesized from 22-(p-toluene­sulfonyl­oxymeth­yl)-6β-meth­oxy-3α,5-cyclo-5α-pregnane; for its crystal structure, see: Ketuly et al. (1997 [triangle]).

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Object name is e-65-o1125-scheme1.jpg

Experimental

Crystal data

  • C23H37IO
  • M r = 456.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1125-efi1.jpg
  • a = 7.4001 (1) Å
  • b = 9.8862 (1) Å
  • c = 14.8768 (2) Å
  • β = 100.593 (1)°
  • V = 1069.82 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.51 mm−1
  • T = 100 K
  • 0.35 × 0.20 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.605, T max = 0.746 (expected range = 0.752–0.928)
  • 10136 measured reflections
  • 4895 independent reflections
  • 4652 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.057
  • S = 0.91
  • 4895 reflections
  • 226 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 1.08 e Å−3
  • Δρmin = −0.40 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2124 Friedel pairs
  • Flack parameter: 0.00 (1)

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014597/tk2434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014597/tk2434Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The reactant, 22-(p-toluenesulfonyloxymethyl)-6β-methoxy-3α,5-cyclo-5α-pregnane (250 mg, 0.5 mmol) and sodium iodide (756 mg, 5.0 mmol) were dissolved in acetone and the solution heated for 12 h. The solvent was removed and water added. The organic compound was extracted with ethyl acetate. The ethyl acetate was removed to furnish 228 mg of crude product. This was chromatographed through silica gel and eluted with hexane–ethyl acetate (8:1 v/v). The second fraction was a viscous oil (223 mg); this slowly solidified. Single crystals were obtained by vacuum sublimation, m.p. 375–376 K.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.98–1.00 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). The final difference Fourier map had a peak/hole in the vicinity of the iodide atom.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C23H37IO at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C23H37IOF(000) = 472
Mr = 456.43Dx = 1.417 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7037 reflections
a = 7.4001 (1) Åθ = 2.5–28.3°
b = 9.8862 (1) ŵ = 1.51 mm1
c = 14.8768 (2) ÅT = 100 K
β = 100.593 (1)°Wedge, colorless
V = 1069.82 (2) Å30.35 × 0.20 × 0.05 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer4895 independent reflections
Radiation source: fine-focus sealed tube4652 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.605, Tmax = 0.746k = −12→12
10136 measured reflectionsl = −18→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.057w = 1/[σ2(Fo2) + (0.0354P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.001
4895 reflectionsΔρmax = 1.08 e Å3
226 parametersΔρmin = −0.40 e Å3
1 restraintAbsolute structure: Flack (1983), 2124 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.00 (1)

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

xyzUiso*/Ueq
I10.49950 (2)0.50001 (3)0.779194 (9)0.03191 (5)
O10.4077 (3)0.27281 (19)0.11997 (13)0.0285 (4)
C10.4448 (4)0.2961 (3)0.72899 (18)0.0265 (5)
H1A0.56220.25480.72020.032*
H1B0.39860.24290.77640.032*
C20.3067 (3)0.2842 (2)0.63954 (17)0.0233 (5)
H20.29400.18540.62540.028*
C30.1162 (4)0.3333 (3)0.6515 (2)0.0348 (6)
H3A0.08030.28680.70370.052*
H3B0.02650.31330.59600.052*
H3C0.11990.43100.66250.052*
C40.3755 (3)0.3500 (2)0.55863 (16)0.0178 (4)
H40.38380.44950.57060.021*
C50.5707 (3)0.3009 (2)0.54875 (17)0.0203 (5)
H5A0.66580.36190.58240.024*
H5B0.59320.20830.57360.024*
C60.5768 (3)0.3026 (3)0.44530 (17)0.0221 (5)
H6A0.68600.35250.43330.027*
H6B0.57940.20960.42100.027*
C70.3996 (3)0.3752 (2)0.40278 (15)0.0155 (4)
H70.42230.47350.41630.019*
C80.2589 (3)0.3300 (2)0.46145 (16)0.0168 (4)
C90.2055 (3)0.1797 (2)0.44589 (18)0.0241 (5)
H9A0.11820.15460.48520.036*
H9B0.31590.12340.46090.036*
H9C0.14850.16580.38170.036*
C100.0911 (3)0.4223 (2)0.43631 (16)0.0188 (5)
H10A−0.00480.39430.47100.023*
H10B0.12670.51660.45360.023*
C110.0133 (3)0.4157 (2)0.33377 (16)0.0198 (5)
H11A−0.09220.47850.31960.024*
H11B−0.03300.32310.31820.024*
C120.1541 (3)0.4519 (2)0.27403 (15)0.0162 (4)
H120.19140.54760.28930.019*
C130.3311 (3)0.3658 (2)0.29976 (15)0.0163 (4)
H130.30170.26930.28290.020*
C140.4773 (3)0.4161 (2)0.24774 (17)0.0191 (4)
H14A0.51170.50990.26710.023*
H14B0.58850.35910.26380.023*
C150.4129 (3)0.4134 (2)0.14454 (16)0.0203 (5)
H150.50560.46070.11460.024*
C160.4180 (4)0.2496 (3)0.02721 (19)0.0359 (7)
H16A0.41220.15220.01490.054*
H16B0.53410.28590.01460.054*
H16C0.31480.2948−0.01210.054*
C170.2296 (3)0.4825 (3)0.11759 (14)0.0199 (5)
C180.1735 (4)0.5323 (2)0.01961 (17)0.0261 (6)
H18A0.26230.5201−0.02210.031*
H18B0.04270.5230−0.00980.031*
C190.2204 (4)0.6337 (3)0.09593 (17)0.0240 (5)
H190.33740.68630.10170.029*
C200.0609 (4)0.6938 (3)0.1333 (2)0.0260 (6)
H20A−0.00770.75970.08980.031*
H20B0.10440.73960.19250.031*
C21−0.0598 (3)0.5708 (3)0.14540 (17)0.0229 (5)
H21A−0.14830.55260.08820.027*
H21B−0.12950.58740.19520.027*
C220.0730 (3)0.4498 (2)0.16951 (16)0.0189 (4)
C23−0.0222 (4)0.3158 (3)0.13919 (19)0.0249 (5)
H23A0.06450.24110.15600.037*
H23B−0.06400.31660.07270.037*
H23C−0.12820.30390.16940.037*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.04946 (10)0.02171 (7)0.02581 (8)−0.00363 (10)0.01026 (6)0.00349 (9)
O10.0350 (10)0.0228 (9)0.0314 (10)0.0019 (7)0.0159 (8)−0.0082 (8)
C10.0330 (13)0.0179 (12)0.0293 (13)0.0001 (10)0.0075 (11)0.0068 (10)
C20.0240 (12)0.0204 (12)0.0264 (12)−0.0007 (9)0.0070 (10)0.0073 (10)
C30.0265 (13)0.0503 (18)0.0310 (14)0.0035 (12)0.0141 (11)0.0173 (13)
C40.0161 (10)0.0155 (10)0.0222 (11)0.0004 (8)0.0047 (8)0.0032 (8)
C50.0161 (10)0.0167 (11)0.0281 (12)0.0010 (8)0.0040 (9)0.0031 (9)
C60.0156 (10)0.0223 (12)0.0301 (13)0.0035 (9)0.0085 (9)0.0004 (10)
C70.0121 (9)0.0142 (10)0.0215 (11)−0.0001 (8)0.0062 (8)−0.0012 (8)
C80.0137 (9)0.0134 (10)0.0241 (11)−0.0021 (8)0.0057 (8)0.0006 (8)
C90.0254 (12)0.0174 (11)0.0298 (13)−0.0069 (9)0.0063 (10)−0.0003 (10)
C100.0128 (10)0.0220 (12)0.0227 (12)0.0015 (8)0.0059 (8)0.0000 (9)
C110.0107 (10)0.0243 (12)0.0247 (12)0.0024 (8)0.0042 (9)0.0018 (9)
C120.0138 (9)0.0169 (9)0.0185 (11)−0.0002 (7)0.0045 (8)−0.0011 (8)
C130.0128 (9)0.0148 (10)0.0221 (11)−0.0003 (8)0.0052 (8)−0.0041 (8)
C140.0144 (10)0.0213 (12)0.0232 (11)−0.0006 (8)0.0075 (8)−0.0032 (9)
C150.0196 (11)0.0209 (11)0.0226 (12)−0.0004 (9)0.0093 (9)−0.0053 (9)
C160.0444 (17)0.0369 (15)0.0239 (14)0.0115 (13)−0.0005 (12)−0.0120 (11)
C170.0191 (9)0.0223 (16)0.0195 (9)−0.0019 (10)0.0063 (7)−0.0023 (10)
C180.0302 (12)0.0283 (17)0.0206 (11)−0.0009 (9)0.0071 (9)−0.0012 (9)
C190.0279 (12)0.0218 (11)0.0243 (12)−0.0006 (9)0.0099 (10)−0.0002 (10)
C200.0295 (14)0.0219 (13)0.0287 (14)0.0022 (11)0.0111 (12)0.0036 (10)
C210.0190 (12)0.0274 (14)0.0229 (12)0.0043 (10)0.0053 (9)0.0031 (10)
C220.0177 (11)0.0217 (10)0.0176 (11)−0.0015 (8)0.0040 (9)−0.0014 (8)
C230.0217 (12)0.0286 (14)0.0239 (13)−0.0046 (11)0.0029 (11)−0.0042 (10)

Geometric parameters (Å, °)

I1—C12.162 (3)C11—H11A0.9900
O1—C161.415 (3)C11—H11B0.9900
O1—C151.436 (3)C12—C131.551 (3)
C1—C21.526 (4)C12—C221.561 (3)
C1—H1A0.9900C12—H121.0000
C1—H1B0.9900C13—C141.525 (3)
C2—C31.532 (3)C13—H131.0000
C2—C41.535 (3)C14—C151.522 (3)
C2—H21.0000C14—H14A0.9900
C3—H3A0.9800C14—H14B0.9900
C3—H3B0.9800C15—C171.506 (3)
C3—H3C0.9800C15—H151.0000
C4—C51.556 (3)C16—H16A0.9800
C4—C81.554 (3)C16—H16B0.9800
C4—H41.0000C16—H16C0.9800
C5—C61.548 (3)C17—C181.522 (3)
C5—H5A0.9900C17—C191.528 (4)
C5—H5B0.9900C17—C221.540 (3)
C6—C71.527 (3)C18—C191.507 (3)
C6—H6A0.9900C18—H18A0.9900
C6—H6B0.9900C18—H18B0.9900
C7—C131.526 (3)C19—C201.516 (3)
C7—C81.542 (3)C19—H191.0000
C7—H71.0000C20—C211.539 (4)
C8—C101.531 (3)C20—H20A0.9900
C8—C91.544 (3)C20—H20B0.9900
C9—H9A0.9800C21—C221.548 (3)
C9—H9B0.9800C21—H21A0.9900
C9—H9C0.9800C21—H21B0.9900
C10—C111.530 (3)C22—C231.529 (4)
C10—H10A0.9900C23—H23A0.9800
C10—H10B0.9900C23—H23B0.9800
C11—C121.531 (3)C23—H23C0.9800
C16—O1—C15113.7 (2)C11—C12—H12106.2
C2—C1—I1115.24 (16)C13—C12—H12106.2
C2—C1—H1A108.5C22—C12—H12106.2
I1—C1—H1A108.5C7—C13—C14110.75 (18)
C2—C1—H1B108.5C7—C13—C12108.88 (17)
I1—C1—H1B108.5C14—C13—C12109.95 (18)
H1A—C1—H1B107.5C7—C13—H13109.1
C1—C2—C3110.9 (2)C14—C13—H13109.1
C1—C2—C4112.66 (19)C12—C13—H13109.1
C3—C2—C4113.7 (2)C15—C14—C13112.72 (18)
C1—C2—H2106.3C15—C14—H14A109.0
C3—C2—H2106.3C13—C14—H14A109.0
C4—C2—H2106.3C15—C14—H14B109.0
C2—C3—H3A109.5C13—C14—H14B109.0
C2—C3—H3B109.5H14A—C14—H14B107.8
H3A—C3—H3B109.5O1—C15—C17113.0 (2)
C2—C3—H3C109.5O1—C15—C14105.24 (19)
H3A—C3—H3C109.5C17—C15—C14111.13 (18)
H3B—C3—H3C109.5O1—C15—H15109.1
C2—C4—C5112.93 (19)C17—C15—H15109.1
C2—C4—C8117.91 (18)C14—C15—H15109.1
C5—C4—C8103.81 (18)O1—C16—H16A109.5
C2—C4—H4107.2O1—C16—H16B109.5
C5—C4—H4107.2H16A—C16—H16B109.5
C8—C4—H4107.2O1—C16—H16C109.5
C6—C5—C4106.72 (18)H16A—C16—H16C109.5
C6—C5—H5A110.4H16B—C16—H16C109.5
C4—C5—H5A110.4C15—C17—C18118.38 (19)
C6—C5—H5B110.4C15—C17—C19120.2 (2)
C4—C5—H5B110.4C18—C17—C1959.22 (17)
H5A—C5—H5B108.6C15—C17—C22119.7 (2)
C7—C6—C5103.72 (17)C18—C17—C22116.76 (18)
C7—C6—H6A111.0C19—C17—C22107.6 (2)
C5—C6—H6A111.0C19—C18—C1760.60 (17)
C7—C6—H6B111.0C19—C18—H18A117.7
C5—C6—H6B111.0C17—C18—H18A117.7
H6A—C6—H6B109.0C19—C18—H18B117.7
C13—C7—C6119.24 (18)C17—C18—H18B117.7
C13—C7—C8114.63 (18)H18A—C18—H18B114.8
C6—C7—C8104.30 (18)C18—C19—C20116.8 (2)
C13—C7—H7105.9C18—C19—C1760.18 (15)
C6—C7—H7105.9C20—C19—C17108.3 (2)
C8—C7—H7105.9C18—C19—H19119.1
C10—C8—C9111.27 (18)C20—C19—H19119.1
C10—C8—C7106.90 (18)C17—C19—H19119.1
C9—C8—C7112.00 (19)C19—C20—C21104.0 (2)
C10—C8—C4116.00 (18)C19—C20—H20A111.0
C9—C8—C4110.17 (19)C21—C20—H20A111.0
C7—C8—C499.95 (16)C19—C20—H20B111.0
C8—C9—H9A109.5C21—C20—H20B111.0
C8—C9—H9B109.5H20A—C20—H20B109.0
H9A—C9—H9B109.5C20—C21—C22106.28 (19)
C8—C9—H9C109.5C20—C21—H21A110.5
H9A—C9—H9C109.5C22—C21—H21A110.5
H9B—C9—H9C109.5C20—C21—H21B110.5
C11—C10—C8110.97 (18)C22—C21—H21B110.5
C11—C10—H10A109.4H21A—C21—H21B108.7
C8—C10—H10A109.4C23—C22—C17112.5 (2)
C11—C10—H10B109.4C23—C22—C21111.27 (19)
C8—C10—H10B109.4C17—C22—C21103.0 (2)
H10A—C10—H10B108.0C23—C22—C12112.2 (2)
C10—C11—C12113.42 (18)C17—C22—C12108.04 (17)
C10—C11—H11A108.9C21—C22—C12109.40 (18)
C12—C11—H11A108.9C22—C23—H23A109.5
C10—C11—H11B108.9C22—C23—H23B109.5
C12—C11—H11B108.9H23A—C23—H23B109.5
H11A—C11—H11B107.7C22—C23—H23C109.5
C11—C12—C13111.24 (18)H23A—C23—H23C109.5
C11—C12—C22113.39 (18)H23B—C23—H23C109.5
C13—C12—C22113.05 (18)
I1—C1—C2—C3−64.1 (2)C16—O1—C15—C1780.7 (3)
I1—C1—C2—C464.7 (2)C16—O1—C15—C14−157.8 (2)
C1—C2—C4—C551.6 (3)C13—C14—C15—O1−71.9 (2)
C3—C2—C4—C5178.9 (2)C13—C14—C15—C1750.8 (3)
C1—C2—C4—C8172.75 (19)O1—C15—C17—C18−82.4 (3)
C3—C2—C4—C8−59.9 (3)C14—C15—C17—C18159.5 (2)
C2—C4—C5—C6147.8 (2)O1—C15—C17—C19−151.4 (2)
C8—C4—C5—C619.0 (2)C14—C15—C17—C1990.5 (2)
C4—C5—C6—C79.6 (2)O1—C15—C17—C2271.3 (3)
C5—C6—C7—C13−164.53 (19)C14—C15—C17—C22−46.7 (3)
C5—C6—C7—C8−35.1 (2)C15—C17—C18—C19−110.1 (3)
C13—C7—C8—C10−60.0 (2)C22—C17—C18—C1995.4 (3)
C6—C7—C8—C10167.79 (18)C17—C18—C19—C20−96.6 (2)
C13—C7—C8—C962.1 (2)C15—C17—C19—C18107.1 (2)
C6—C7—C8—C9−70.1 (2)C22—C17—C19—C18−111.1 (2)
C13—C7—C8—C4178.74 (18)C15—C17—C19—C20−142.0 (2)
C6—C7—C8—C446.6 (2)C18—C17—C19—C20110.9 (2)
C2—C4—C8—C1080.4 (2)C22—C17—C19—C20−0.2 (3)
C5—C4—C8—C10−153.86 (18)C18—C19—C20—C2145.7 (3)
C2—C4—C8—C9−47.1 (3)C17—C19—C20—C21−19.4 (3)
C5—C4—C8—C978.6 (2)C19—C20—C21—C2232.1 (3)
C2—C4—C8—C7−165.15 (19)C15—C17—C22—C23−78.5 (3)
C5—C4—C8—C7−39.4 (2)C18—C17—C22—C2375.7 (3)
C9—C8—C10—C11−65.6 (2)C19—C17—C22—C23139.5 (2)
C7—C8—C10—C1157.0 (2)C15—C17—C22—C21161.6 (2)
C4—C8—C10—C11167.43 (18)C18—C17—C22—C21−44.3 (3)
C8—C10—C11—C12−56.8 (3)C19—C17—C22—C2119.6 (2)
C10—C11—C12—C1353.2 (3)C15—C17—C22—C1245.9 (3)
C10—C11—C12—C22−178.09 (19)C18—C17—C22—C12−160.0 (2)
C6—C7—C13—C14−57.0 (3)C19—C17—C22—C12−96.2 (2)
C8—C7—C13—C14178.40 (17)C20—C21—C22—C23−152.6 (2)
C6—C7—C13—C12−177.97 (19)C20—C21—C22—C17−31.9 (2)
C8—C7—C13—C1257.4 (2)C20—C21—C22—C1282.9 (2)
C11—C12—C13—C7−51.4 (2)C11—C12—C22—C23−53.4 (3)
C22—C12—C13—C7179.68 (18)C13—C12—C22—C2374.4 (2)
C11—C12—C13—C14−172.89 (19)C11—C12—C22—C17−177.9 (2)
C22—C12—C13—C1458.2 (2)C13—C12—C22—C17−50.1 (3)
C7—C13—C14—C15−177.95 (19)C11—C12—C22—C2170.6 (2)
C12—C13—C14—C15−57.6 (2)C13—C12—C22—C21−161.57 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2434).

References

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