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In the title mol­ecule, C22H29ClO4, all bond lengths and angles show normal values. Rings A and C have slightly distorted chair conformations, while rings B and D show envelope conformations. Weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into chains running along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056145/cv2163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056145/cv2163Isup2.hkl
Contains datablock I

CCDC reference: 636224

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.128
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.49 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT338_ALERT_2_C Small Average Tau in cyclohexane C5 -C10 34.42 Deg.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 4150 Count of symmetry unique reflns 2390 Completeness (_total/calc) 173.64% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1760 Fraction of Friedel pairs measured 0.736 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 14 ALERT level G = General alerts; check 13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.05; Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3β-Acetoxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one top
Crystal data top
C22H29ClO4F(000) = 420
Mr = 392.90Dx = 1.291 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 841 reflections
a = 11.741 (5) Åθ = 3.4–26.0°
b = 6.911 (3) ŵ = 0.21 mm1
c = 12.457 (5) ÅT = 293 K
β = 90.958 (5)°Prismatic, colourless
V = 1010.7 (7) Å30.20 × 0.15 × 0.14 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
3484 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 27.0°, θmin = 1.6°
φ and ω scansh = 1414
4915 measured reflectionsk = 88
4150 independent reflectionsl = 915
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0809P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.35 e Å3
4150 reflectionsΔρmin = 0.35 e Å3
248 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.062 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with how many Friedel pairs?
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (7)
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
Cl10.65638 (6)0.33471 (13)0.06395 (5)0.0711 (3)
O10.14366 (14)0.4115 (4)0.07417 (14)0.0650 (6)
O20.2083 (2)0.3478 (6)0.0863 (2)0.1164 (11)
O30.45286 (16)0.1328 (2)0.28765 (18)0.0585 (5)
O40.99306 (18)0.7114 (4)0.3824 (2)0.0801 (7)
C10.38676 (19)0.6600 (3)0.2136 (2)0.0439 (5)
H1A0.39000.77800.25570.053*
H1B0.43090.68150.14960.053*
C20.2627 (2)0.6248 (4)0.1792 (2)0.0488 (6)
H2A0.21520.61280.24180.059*
H2B0.23470.73230.13610.059*
C30.25903 (19)0.4424 (4)0.1152 (2)0.0507 (6)
H30.31110.45360.05480.061*
C40.2944 (2)0.2738 (4)0.1843 (2)0.0530 (6)
H4A0.29010.15560.14250.064*
H4B0.24260.26170.24380.064*
C50.41482 (19)0.3010 (3)0.22726 (19)0.0440 (5)
C60.5018 (2)0.1720 (4)0.1863 (2)0.0533 (7)
H60.47840.08700.12700.064*
C70.6248 (2)0.2251 (4)0.1921 (2)0.0481 (6)
H70.67010.10690.20060.058*
C80.65179 (18)0.3603 (3)0.28477 (17)0.0377 (5)
H80.63900.29190.35240.045*
C90.57468 (18)0.5395 (3)0.27993 (17)0.0344 (5)
H90.58930.59880.21000.041*
C100.44436 (18)0.4972 (3)0.27940 (17)0.0346 (5)
C110.6106 (2)0.6939 (4)0.3637 (2)0.0448 (6)
H11A0.56790.81150.34940.054*
H11B0.58990.64840.43440.054*
C120.7379 (2)0.7424 (4)0.3650 (2)0.0480 (6)
H12A0.75810.80400.29800.058*
H12B0.75520.83150.42320.058*
C130.80620 (19)0.5575 (4)0.37997 (19)0.0431 (5)
C140.77437 (19)0.4300 (4)0.28310 (18)0.0418 (5)
H140.77670.51830.22160.050*
C150.8724 (2)0.2919 (5)0.2654 (2)0.0599 (7)
H150.88020.23510.19390.072*
C160.9767 (2)0.3903 (5)0.3160 (3)0.0715 (9)
H161.04780.39330.27590.086*
C170.9352 (2)0.5714 (4)0.3647 (2)0.0558 (7)
C180.7857 (2)0.4777 (5)0.4939 (2)0.0587 (7)
H18A0.85710.44060.52630.088*
H18B0.73640.36710.48930.088*
H18C0.75070.57590.53680.088*
C190.3957 (2)0.4926 (4)0.3920 (2)0.0552 (7)
H19A0.31790.44960.38840.083*
H19B0.39880.62000.42260.083*
H19C0.43950.40520.43610.083*
C200.9331 (2)0.1980 (5)0.3558 (3)0.0738 (10)
H20A0.97780.08370.34030.089*
H20B0.89590.19600.42470.089*
C210.1306 (3)0.3668 (5)0.0282 (2)0.0632 (7)
C220.0088 (3)0.3531 (7)0.0623 (3)0.0955 (13)
H22A0.00900.45610.11150.143*
H22B0.03860.36350.00050.143*
H22C0.00460.23090.09690.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0788 (5)0.0908 (6)0.0437 (3)0.0003 (4)0.0010 (3)0.0246 (4)
O10.0426 (9)0.0966 (16)0.0554 (11)0.0085 (10)0.0094 (8)0.0007 (10)
O20.1015 (19)0.178 (3)0.0693 (15)0.038 (2)0.0047 (13)0.035 (2)
O30.0581 (11)0.0286 (8)0.0886 (15)0.0030 (8)0.0065 (10)0.0095 (9)
O40.0606 (12)0.0726 (14)0.1066 (18)0.0241 (11)0.0171 (12)0.0043 (13)
C10.0428 (12)0.0387 (12)0.0501 (13)0.0004 (10)0.0019 (10)0.0095 (10)
C20.0437 (13)0.0481 (14)0.0545 (15)0.0016 (11)0.0024 (11)0.0122 (12)
C30.0361 (11)0.0693 (18)0.0467 (13)0.0046 (12)0.0028 (10)0.0055 (13)
C40.0433 (13)0.0438 (14)0.0717 (17)0.0065 (11)0.0049 (12)0.0037 (12)
C50.0428 (12)0.0342 (12)0.0547 (13)0.0032 (10)0.0067 (10)0.0024 (10)
C60.0537 (14)0.0331 (13)0.0725 (18)0.0012 (11)0.0158 (13)0.0170 (12)
C70.0507 (13)0.0374 (12)0.0559 (14)0.0086 (11)0.0086 (11)0.0116 (11)
C80.0397 (10)0.0362 (11)0.0371 (10)0.0023 (10)0.0050 (8)0.0013 (9)
C90.0401 (11)0.0311 (11)0.0318 (11)0.0014 (9)0.0020 (8)0.0026 (9)
C100.0381 (11)0.0302 (10)0.0354 (11)0.0004 (9)0.0011 (9)0.0036 (9)
C110.0517 (13)0.0356 (12)0.0468 (13)0.0028 (11)0.0052 (10)0.0114 (10)
C120.0549 (14)0.0393 (13)0.0494 (13)0.0063 (11)0.0091 (11)0.0088 (11)
C130.0424 (12)0.0441 (13)0.0427 (13)0.0040 (10)0.0066 (10)0.0033 (10)
C140.0423 (12)0.0438 (13)0.0393 (12)0.0001 (10)0.0000 (9)0.0045 (10)
C150.0446 (14)0.0695 (19)0.0655 (16)0.0053 (13)0.0018 (11)0.0182 (15)
C160.0397 (13)0.082 (2)0.093 (2)0.0020 (15)0.0008 (13)0.0156 (19)
C170.0461 (14)0.0638 (18)0.0570 (16)0.0110 (14)0.0099 (12)0.0014 (13)
C180.0611 (15)0.0722 (19)0.0427 (14)0.0027 (15)0.0074 (11)0.0038 (13)
C190.0581 (15)0.0640 (17)0.0438 (14)0.0072 (14)0.0103 (11)0.0037 (13)
C200.0527 (16)0.060 (2)0.107 (3)0.0166 (16)0.0235 (17)0.0116 (18)
C210.0728 (18)0.0582 (17)0.0580 (16)0.0138 (16)0.0165 (14)0.0035 (14)
C220.084 (2)0.101 (3)0.100 (3)0.025 (2)0.044 (2)0.008 (2)
Geometric parameters (Å, º) top
Cl1—C71.811 (3)C10—C191.524 (3)
O1—C211.319 (3)C11—C121.532 (3)
O1—C31.456 (3)C11—H11A0.9700
O2—C211.182 (4)C11—H11B0.9700
O3—C61.421 (4)C12—C131.519 (3)
O3—C51.451 (3)C12—H12A0.9700
O4—C171.201 (3)C12—H12B0.9700
C1—C21.531 (3)C13—C171.532 (4)
C1—C101.542 (3)C13—C141.535 (3)
C1—H1A0.9700C13—C181.545 (4)
C1—H1B0.9700C14—C151.514 (4)
C2—C31.492 (4)C14—H140.9800
C2—H2A0.9700C15—C201.473 (4)
C2—H2B0.9700C15—C161.528 (4)
C3—C41.503 (4)C15—H150.9800
C3—H30.9800C16—C171.477 (5)
C4—C51.515 (3)C16—C201.511 (5)
C4—H4A0.9700C16—H160.9800
C4—H4B0.9700C18—H18A0.9599
C5—C61.454 (4)C18—H18B0.9599
C5—C101.541 (3)C18—H18C0.9599
C6—C71.490 (4)C19—H19A0.9599
C6—H60.9800C19—H19B0.9599
C7—C81.515 (3)C19—H19C0.9599
C7—H70.9800C20—H20A0.9700
C8—C141.518 (3)C20—H20B0.9700
C8—C91.535 (3)C21—C221.488 (4)
C8—H80.9800C22—H22A0.9599
C9—C111.546 (3)C22—H22B0.9599
C9—C101.558 (3)C22—H22C0.9599
C9—H90.9800
C21—O1—C3117.8 (2)C9—C11—H11A108.7
C6—O3—C560.81 (16)C12—C11—H11B108.7
C2—C1—C10116.12 (19)C9—C11—H11B108.7
C2—C1—H1A108.3H11A—C11—H11B107.6
C10—C1—H1A108.3C13—C12—C11109.30 (19)
C2—C1—H1B108.3C13—C12—H12A109.8
C10—C1—H1B108.3C11—C12—H12A109.8
H1A—C1—H1B107.4C13—C12—H12B109.8
C3—C2—C1107.6 (2)C11—C12—H12B109.8
C3—C2—H2A110.2H12A—C12—H12B108.3
C1—C2—H2A110.2C12—C13—C17116.9 (2)
C3—C2—H2B110.2C12—C13—C14105.38 (17)
C1—C2—H2B110.2C17—C13—C1499.58 (19)
H2A—C2—H2B108.5C12—C13—C18108.8 (2)
O1—C3—C2109.3 (2)C17—C13—C18107.83 (19)
O1—C3—C4109.5 (2)C14—C13—C18118.5 (2)
C2—C3—C4110.1 (2)C15—C14—C8121.7 (2)
O1—C3—H3109.3C15—C14—C13107.47 (19)
C2—C3—H3109.3C8—C14—C13112.94 (19)
C4—C3—H3109.3C15—C14—H14104.3
C3—C4—C5110.7 (2)C8—C14—H14104.3
C3—C4—H4A109.5C13—C14—H14104.3
C5—C4—H4A109.5C20—C15—C14121.7 (3)
C3—C4—H4B109.5C20—C15—C1660.4 (2)
C5—C4—H4B109.5C14—C15—C16105.4 (2)
H4A—C4—H4B108.1C20—C15—H15117.9
O3—C5—C658.59 (17)C14—C15—H15117.9
O3—C5—C4111.16 (19)C16—C15—H15117.9
C6—C5—C4117.2 (2)C17—C16—C20119.6 (3)
O3—C5—C10114.93 (17)C17—C16—C15106.1 (2)
C6—C5—C10122.2 (2)C20—C16—C1558.0 (2)
C4—C5—C10117.4 (2)C17—C16—H16118.8
O3—C6—C560.61 (16)C20—C16—H16118.8
O3—C6—C7114.2 (2)C15—C16—H16118.8
C5—C6—C7121.2 (2)O4—C17—C16124.6 (3)
O3—C6—H6116.3O4—C17—C13125.8 (3)
C5—C6—H6116.3C16—C17—C13109.4 (2)
C7—C6—H6116.3C13—C18—H18A109.5
C6—C7—C8112.3 (2)C13—C18—H18B109.5
C6—C7—Cl1105.87 (18)H18A—C18—H18B109.5
C8—C7—Cl1111.72 (17)C13—C18—H18C109.5
C6—C7—H7109.0H18A—C18—H18C109.5
C8—C7—H7109.0H18B—C18—H18C109.5
Cl1—C7—H7109.0C10—C19—H19A109.5
C7—C8—C14111.83 (18)C10—C19—H19B109.5
C7—C8—C9110.61 (16)H19A—C19—H19B109.5
C14—C8—C9107.59 (19)C10—C19—H19C109.5
C7—C8—H8108.9H19A—C19—H19C109.5
C14—C8—H8108.9H19B—C19—H19C109.5
C9—C8—H8108.9C15—C20—C1661.6 (2)
C8—C9—C11112.13 (17)C15—C20—H20A117.6
C8—C9—C10115.31 (17)C16—C20—H20A117.6
C11—C9—C10112.89 (18)C15—C20—H20B117.6
C8—C9—H9105.1C16—C20—H20B117.6
C11—C9—H9105.1H20A—C20—H20B114.7
C10—C9—H9105.1O2—C21—O1122.7 (3)
C19—C10—C5106.5 (2)O2—C21—C22124.5 (3)
C19—C10—C1109.7 (2)O1—C21—C22112.8 (3)
C5—C10—C1108.93 (17)C21—C22—H22A109.5
C19—C10—C9112.55 (18)C21—C22—H22B109.5
C5—C10—C9112.40 (17)H22A—C22—H22B109.5
C1—C10—C9106.71 (17)C21—C22—H22C109.5
C12—C11—C9114.39 (19)H22A—C22—H22C109.5
C12—C11—H11A108.7H22B—C22—H22C109.5
C10—C1—C2—C357.7 (3)C11—C9—C10—C1939.8 (3)
C21—O1—C3—C2132.3 (3)C8—C9—C10—C529.4 (2)
C21—O1—C3—C4107.0 (3)C11—C9—C10—C5160.07 (18)
C1—C2—C3—O1175.8 (2)C8—C9—C10—C1148.74 (18)
C1—C2—C3—C463.9 (3)C11—C9—C10—C180.6 (2)
O1—C3—C4—C5179.4 (2)C8—C9—C11—C1248.9 (3)
C2—C3—C4—C560.4 (3)C10—C9—C11—C12178.82 (19)
C6—O3—C5—C4109.7 (2)C9—C11—C12—C1354.7 (3)
C6—O3—C5—C10113.9 (2)C11—C12—C13—C17170.1 (2)
C3—C4—C5—O3175.8 (2)C11—C12—C13—C1460.6 (2)
C3—C4—C5—C6111.3 (3)C11—C12—C13—C1867.5 (2)
C3—C4—C5—C1049.0 (3)C7—C8—C14—C1546.4 (3)
C5—O3—C6—C7113.5 (2)C9—C8—C14—C15168.1 (2)
C4—C5—C6—O399.3 (2)C7—C8—C14—C13176.50 (18)
C10—C5—C6—O3101.5 (2)C9—C8—C14—C1361.8 (2)
O3—C5—C6—C7102.1 (3)C12—C13—C14—C15155.1 (2)
C4—C5—C6—C7158.6 (2)C17—C13—C14—C1533.6 (3)
C10—C5—C6—C70.6 (4)C18—C13—C14—C1582.9 (3)
O3—C6—C7—C841.6 (3)C12—C13—C14—C867.9 (2)
C5—C6—C7—C827.5 (4)C17—C13—C14—C8170.5 (2)
O3—C6—C7—Cl1163.72 (17)C18—C13—C14—C854.1 (3)
C5—C6—C7—Cl194.6 (3)C8—C14—C15—C2091.6 (3)
C6—C7—C8—C14174.1 (2)C13—C14—C15—C2040.8 (3)
Cl1—C7—C8—C1455.3 (2)C8—C14—C15—C16156.0 (2)
C6—C7—C8—C954.2 (3)C13—C14—C15—C1623.6 (3)
Cl1—C7—C8—C964.6 (2)C20—C15—C16—C17115.2 (3)
C7—C8—C9—C11172.1 (2)C14—C15—C16—C172.9 (3)
C14—C8—C9—C1149.7 (2)C14—C15—C16—C20118.1 (3)
C7—C8—C9—C1056.8 (3)C20—C16—C17—O4141.8 (3)
C14—C8—C9—C10179.26 (17)C15—C16—C17—O4156.3 (3)
O3—C5—C10—C1955.1 (2)C20—C16—C17—C1342.8 (4)
C6—C5—C10—C19122.4 (3)C15—C16—C17—C1319.1 (3)
C4—C5—C10—C1978.4 (2)C12—C13—C17—O430.2 (4)
O3—C5—C10—C1173.4 (2)C14—C13—C17—O4143.0 (3)
C6—C5—C10—C1119.4 (2)C18—C13—C17—O492.7 (3)
C4—C5—C10—C139.8 (3)C12—C13—C17—C16145.1 (3)
O3—C5—C10—C968.6 (2)C14—C13—C17—C1632.3 (3)
C6—C5—C10—C91.3 (3)C18—C13—C17—C1692.0 (3)
C4—C5—C10—C9157.9 (2)C14—C15—C20—C1690.5 (3)
C2—C1—C10—C1971.8 (3)C17—C16—C20—C1591.2 (3)
C2—C1—C10—C544.4 (3)C3—O1—C21—O21.4 (5)
C2—C1—C10—C9166.0 (2)C3—O1—C21—C22175.8 (3)
C8—C9—C10—C1990.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O3i0.972.593.480 (3)153
Symmetry code: (i) x, y+1, z.
 

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