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The title compound, C20H25ClO3, is built up from four fused rings, three of which are six-membered and one five-membered. The ring adjacent to the five-membered ring adopts a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018708/tk2040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018708/tk2040Isup2.hkl
Contains datablock I

CCDC reference: 610916

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.066
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C20 .. 7.32 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.07 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
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 27.50 From the CIF: _reflns_number_total 4116 Count of symmetry unique reflns 2367 Completeness (_total/calc) 173.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1749 Fraction of Friedel pairs measured 0.739 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

13-Methyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro- 1H-cyclopenta[a]phenanthren-17-yl 2-chloroacetate top
Crystal data top
C20H25ClO3F(000) = 744.00
Mr = 348.85Dx = 1.285 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2abCell parameters from 13502 reflections
a = 7.499 (2) Åθ = 3.0–27.5°
b = 15.365 (5) ŵ = 0.23 mm1
c = 15.647 (4) ÅT = 298 K
V = 1802.9 (9) Å3Chunk, colorless
Z = 40.26 × 0.21 × 0.14 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2498 reflections with F2 > 2σ(F2)
Detector resolution: 10.0 pixels mm-1Rint = 0.034
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.918, Tmax = 0.969k = 1919
17271 measured reflectionsl = 2019
4116 independent reflections
Refinement top
Refinement on F2(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.036Δρmax = 0.24 e Å3
wR(F2) = 0.066Δρmin = 0.19 e Å3
S = 1.01Extinction correction: Larson (1970), equation 22
4116 reflectionsExtinction coefficient: 112 (15)
219 parametersAbsolute structure: Flack (1983), with 1758 Friedel pairs
H-atom parameters constrainedAbsolute structure parameter: 0.054 (5)
w = 1/[1.0800σ(Fo2)]/(4Fo2)
Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.83719 (8)0.09270 (4)0.77193 (3)0.07901 (18)
O10.6732 (2)0.97219 (9)0.58327 (9)0.1026 (6)
O20.72856 (18)0.25442 (8)0.58983 (6)0.0601 (3)
O30.9229 (2)0.26526 (10)0.69734 (9)0.0930 (6)
C10.7281 (2)0.47503 (11)0.50088 (9)0.0479 (5)
C20.6380 (2)0.56276 (11)0.50757 (9)0.0473 (5)
C30.6553 (2)0.61813 (12)0.42961 (10)0.0557 (5)
C40.6663 (2)0.70382 (12)0.43255 (10)0.0568 (6)
C50.6629 (2)0.75210 (12)0.51193 (10)0.0517 (5)
C60.6758 (2)0.83927 (12)0.51169 (11)0.0590 (6)
C70.6653 (2)0.89348 (13)0.58731 (12)0.0674 (6)
C80.6422 (3)0.84671 (12)0.67129 (12)0.0721 (7)
C90.7113 (2)0.75364 (12)0.66966 (10)0.0581 (6)
C100.6358 (2)0.70196 (11)0.59474 (10)0.0479 (5)
C110.7117 (2)0.61016 (11)0.58667 (9)0.0448 (4)
C120.6835 (2)0.55417 (10)0.66694 (9)0.0539 (5)
C130.7570 (2)0.46156 (11)0.65813 (10)0.0549 (5)
C140.6874 (2)0.41651 (11)0.57805 (9)0.0445 (4)
C150.7885 (2)0.33497 (11)0.54980 (10)0.0534 (5)
C160.7543 (3)0.32620 (12)0.45330 (10)0.0706 (7)
C170.6953 (2)0.41631 (11)0.42340 (9)0.0681 (6)
C180.8069 (3)0.22846 (12)0.66177 (11)0.0547 (6)
C190.7199 (2)0.14513 (12)0.69018 (11)0.0626 (6)
C200.4878 (2)0.39485 (13)0.58625 (12)0.0648 (6)
H10.85660.48630.50230.058*
H20.51060.55250.51720.057*
H30.65840.59100.37650.067*
H40.67670.73440.38150.068*
H60.69260.86680.45940.071*
H100.50700.69640.60380.057*
H110.84080.61600.57850.054*
H150.91630.34290.56010.064*
H810.70630.87860.71510.087*
H820.51620.84550.68530.087*
H910.84030.75490.66500.070*
H920.67760.72500.72250.070*
H1210.74280.58220.71470.065*
H1220.55660.55060.67840.065*
H1310.88610.46430.65530.066*
H1320.72150.42800.70780.066*
H1610.86260.30870.42400.085*
H1620.66140.28370.44250.085*
H1710.76580.43530.37490.082*
H1720.57000.41610.40790.082*
H1910.60080.15830.71060.075*
H1920.71240.10620.64150.075*
H2010.42260.44690.59950.078*
H2020.44520.37110.53330.078*
H2030.47100.35300.63110.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0980 (4)0.0720 (3)0.0670 (2)0.0064 (3)0.0090 (3)0.0172 (2)
O10.1530 (17)0.0477 (9)0.1073 (10)0.0009 (10)0.0192 (13)0.0102 (8)
O20.0714 (9)0.0469 (7)0.0619 (6)0.0040 (7)0.0139 (6)0.0071 (6)
O30.1088 (13)0.0803 (11)0.0897 (10)0.0295 (10)0.0462 (10)0.0204 (8)
C10.0541 (12)0.0498 (10)0.0399 (8)0.0028 (9)0.0007 (9)0.0003 (8)
C20.0503 (11)0.0508 (11)0.0406 (8)0.0013 (9)0.0031 (8)0.0019 (8)
C30.0658 (12)0.0611 (13)0.0401 (9)0.0026 (11)0.0026 (9)0.0017 (8)
C40.0644 (13)0.0569 (12)0.0491 (10)0.0032 (11)0.0037 (10)0.0069 (9)
C50.0471 (11)0.0520 (11)0.0560 (10)0.0019 (10)0.0019 (9)0.0035 (9)
C60.0577 (13)0.0566 (12)0.0626 (11)0.0004 (11)0.0049 (10)0.0040 (10)
C70.0670 (14)0.0529 (12)0.0823 (13)0.0010 (12)0.0088 (13)0.0016 (11)
C80.0801 (17)0.0637 (14)0.0725 (12)0.0057 (13)0.0015 (12)0.0209 (11)
C90.0669 (15)0.0558 (11)0.0516 (9)0.0062 (11)0.0002 (9)0.0037 (9)
C100.0436 (11)0.0515 (10)0.0485 (9)0.0048 (9)0.0003 (9)0.0021 (8)
C110.0433 (10)0.0492 (10)0.0419 (8)0.0010 (9)0.0004 (8)0.0018 (8)
C120.0705 (14)0.0541 (11)0.0371 (8)0.0068 (11)0.0018 (9)0.0016 (8)
C130.0689 (14)0.0540 (11)0.0419 (9)0.0050 (11)0.0046 (9)0.0065 (8)
C140.0464 (11)0.0479 (10)0.0391 (8)0.0027 (9)0.0046 (8)0.0011 (7)
C150.0604 (14)0.0462 (10)0.0537 (10)0.0004 (10)0.0034 (9)0.0023 (9)
C160.1002 (18)0.0577 (13)0.0540 (10)0.0108 (13)0.0049 (11)0.0039 (9)
C170.1002 (17)0.0581 (12)0.0460 (9)0.0081 (13)0.0005 (11)0.0044 (9)
C180.0653 (15)0.0473 (12)0.0516 (10)0.0038 (11)0.0057 (10)0.0022 (9)
C190.0702 (15)0.0537 (11)0.0639 (10)0.0039 (11)0.0042 (10)0.0052 (9)
C200.0608 (13)0.0623 (13)0.0713 (12)0.0053 (11)0.0061 (10)0.0007 (11)
Geometric parameters (Å, º) top
Cl1—C191.7488 (19)C18—C191.504 (2)
O1—C71.212 (2)C1—H10.980
O2—C151.458 (2)C2—H20.980
O2—C181.331 (2)C3—H30.930
O3—C181.177 (2)C4—H40.930
C1—C21.511 (2)C6—H60.930
C1—C141.536 (2)C8—H810.970
C1—C171.531 (2)C8—H820.970
C2—C31.493 (2)C9—H910.970
C2—C111.539 (2)C9—H920.970
C3—C41.320 (2)C10—H100.980
C4—C51.447 (2)C11—H110.980
C5—C61.343 (2)C12—H1210.970
C5—C101.521 (2)C12—H1220.970
C6—C71.449 (2)C13—H1310.970
C7—C81.508 (2)C13—H1320.970
C8—C91.521 (2)C15—H150.980
C9—C101.525 (2)C16—H1610.970
C10—C111.526 (2)C16—H1620.970
C11—C121.537 (2)C17—H1710.970
C12—C131.532 (2)C17—H1720.970
C13—C141.524 (2)C19—H1910.970
C14—C151.529 (2)C19—H1920.970
C14—C201.539 (2)C20—H2010.960
C15—C161.537 (2)C20—H2020.960
C16—C171.527 (2)C20—H2030.960
O1···C193.159 (2)H11···H62.717
O3···C93.448 (2)H15···H1622.676
C9···O33.448 (2)H81···Cl13.546
C19···O13.159 (2)H81···O33.556
Cl1···H43.163H81···C203.441
Cl1···H63.006H81···H1323.511
Cl1···H113.382H81···H2013.233
Cl1···H813.546H81···H2032.778
Cl1···H1213.161H82···C33.297
Cl1···H1223.122H82···C43.295
Cl1···H1313.082H82···H33.014
Cl1···H1723.315H82···H43.014
Cl1···H2013.586H82···H1322.754
O1···H12.800H82···H1913.421
O1···H23.003H82···H2032.877
O1···H1713.433H91···O32.796
O1···H1723.438H91···C33.403
O1···H1913.527H91···C42.951
O1···H1922.270H91···H33.424
O2···H1612.919H91···H42.631
O2···H1623.337H92···O33.307
O2···H2023.174H92···C193.501
O3···H42.977H92···H1613.210
O3···H813.556H92···H1713.455
O3···H912.796H92···H1912.551
O3···H923.307H92···H2033.218
O3···H1622.925H121···Cl13.161
O3···H1723.420H121···C173.299
C2···H63.549H121···H1712.522
C3···H823.297H121···H1723.334
C3···H913.403H121···H1913.062
C4···H103.033H122···Cl13.122
C4···H823.295H122···C193.262
C4···H912.951H122···H1713.358
C5···H103.251H122···H1912.674
C5···H113.456H122···H1923.569
C6···H13.600H131···Cl13.082
C6···H23.046H131···H33.580
C6···H103.121H132···C83.547
C6···H112.963H132···H32.804
C7···H13.277H132···H813.511
C7···H23.173H132···H822.754
C7···H113.561H132···H1713.355
C7···H1923.395H161···O22.919
C8···H1323.547H161···C193.298
C8···H2033.208H161···C203.270
C9···H43.585H161···H923.210
C9···H1913.337H161···H1623.376
C10···H43.599H161···H1912.807
C10···H63.589H161···H1923.106
C10···H1913.589H161···H2022.910
C12···H1713.280H161···H2032.753
C12···H1913.283H162···O23.337
C13···H33.568H162···O32.925
C15···H1623.341H162···C153.341
C16···H2023.360H162···C183.125
C16···H2033.459H162···H152.676
C17···H1213.299H162···H1613.376
C18···H43.487H162···H2023.215
C18···H1623.125H162···H2033.336
C18···H1723.165H171···O13.433
C18···H2023.568H171···C123.280
C19···H923.501H171···H923.455
C19···H1223.262H171···H1212.522
C19···H1613.298H171···H1223.358
C19···H1723.184H171···H1323.355
C20···H813.441H171···H1913.189
C20···H1613.270H171···H1923.419
H1···O12.800H172···Cl13.315
H1···C63.600H172···O13.438
H1···C73.277H172···O33.420
H1···H63.436H172···C183.165
H2···O13.003H172···C193.184
H2···C63.046H172···H1213.334
H2···C73.173H172···H1922.812
H2···H62.713H191···O13.527
H3···C133.568H191···C93.337
H3···H823.014H191···C103.589
H3···H913.424H191···C123.283
H3···H1313.580H191···H43.558
H3···H1322.804H191···H103.071
H4···Cl13.163H191···H823.421
H4···O32.977H191···H922.551
H4···C93.585H191···H1213.062
H4···C103.599H191···H1222.674
H4···C183.487H191···H1612.807
H4···H102.705H191···H1713.189
H4···H113.467H192···O12.270
H4···H823.014H192···C73.395
H4···H912.631H192···H1223.569
H4···H1913.558H192···H1613.106
H6···Cl13.006H192···H1713.419
H6···C23.549H192···H1722.812
H6···C103.589H192···H2023.264
H6···H13.436H201···Cl13.586
H6···H22.713H201···H63.467
H6···H102.735H201···H813.233
H6···H112.717H202···O23.174
H6···H2013.467H202···C163.360
H10···C43.033H202···C183.568
H10···C53.251H202···H1612.910
H10···C63.121H202···H1623.215
H10···H42.705H202···H1923.264
H10···H62.735H203···C83.208
H10···H1913.071H203···C163.459
H11···Cl13.382H203···H812.778
H11···C53.456H203···H822.877
H11···C62.963H203···H923.218
H11···C73.561H203···H1612.753
H11···H43.467H203···H1623.336
C15—O2—C18118.80 (14)C7—C6—H6117.7
C2—C1—C14112.27 (13)C7—C8—H81108.5
C2—C1—C17120.58 (14)C7—C8—H82108.5
C14—C1—C17104.22 (13)C9—C8—H81108.5
C1—C2—C3114.39 (13)C9—C8—H82108.5
C1—C2—C11108.50 (13)H81—C8—H82109.5
C3—C2—C11110.87 (14)C8—C9—H91108.8
C2—C3—C4123.05 (14)C8—C9—H92108.8
C3—C4—C5122.70 (15)C10—C9—H91108.8
C4—C5—C6120.51 (15)C10—C9—H92108.8
C4—C5—C10118.29 (16)H91—C9—H92109.5
C6—C5—C10121.14 (15)C5—C10—H10107.4
C5—C6—C7124.55 (16)C9—C10—H10107.4
O1—C7—C6121.88 (18)C11—C10—H10107.4
O1—C7—C8121.77 (18)C2—C11—H11107.1
C6—C7—C8116.35 (17)C10—C11—H11107.1
C7—C8—C9113.22 (16)C12—C11—H11107.1
C8—C9—C10112.08 (15)C11—C12—H121108.5
C5—C10—C9109.97 (14)C11—C12—H122108.5
C5—C10—C11110.35 (13)C13—C12—H121108.5
C9—C10—C11113.97 (14)C13—C12—H122108.5
C2—C11—C10111.70 (13)H121—C12—H122109.5
C2—C11—C12110.05 (13)C12—C13—H131108.9
C10—C11—C12113.47 (12)C12—C13—H132108.9
C11—C12—C13113.38 (13)C14—C13—H131108.9
C12—C13—C14111.89 (14)C14—C13—H132108.9
C1—C14—C13108.21 (13)H131—C13—H132109.5
C1—C14—C1598.86 (12)O2—C15—H15109.6
C1—C14—C20112.65 (14)C14—C15—H15109.6
C13—C14—C15116.11 (14)C16—C15—H15109.6
C13—C14—C20111.27 (14)C15—C16—H161110.4
C15—C14—C20109.20 (14)C15—C16—H162110.4
O2—C15—C14114.74 (14)C17—C16—H161110.4
O2—C15—C16107.23 (13)C17—C16—H162110.4
C14—C15—C16105.86 (14)H161—C16—H162109.5
C15—C16—C17105.65 (13)C1—C17—H171110.8
C1—C17—C16104.19 (12)C1—C17—H172110.8
O2—C18—O3125.59 (17)C16—C17—H171110.8
O2—C18—C19108.29 (16)C16—C17—H172110.8
O3—C18—C19126.12 (17)H171—C17—H172109.5
Cl1—C19—C18112.98 (14)Cl1—C19—H191108.6
C2—C1—H1106.3Cl1—C19—H192108.6
C14—C1—H1106.3C18—C19—H191108.6
C17—C1—H1106.3C18—C19—H192108.6
C1—C2—H2107.6H191—C19—H192109.5
C3—C2—H2107.6C14—C20—H201109.5
C11—C2—H2107.6C14—C20—H202109.5
C2—C3—H3118.5C14—C20—H203109.5
C4—C3—H3118.5H201—C20—H202109.5
C3—C4—H4118.7H201—C20—H203109.5
C5—C4—H4118.7H202—C20—H203109.5
C5—C6—H6117.7
C15—O2—C18—O30.1 (2)C10—C5—C6—C70.1 (2)
C15—O2—C18—C19179.30 (14)C5—C6—C7—O1178.1 (2)
C18—O2—C15—C1491.30 (19)C5—C6—C7—C81.3 (3)
C18—O2—C15—C16151.44 (16)O1—C7—C8—C9155.8 (2)
C2—C1—C14—C1360.89 (19)C6—C7—C8—C924.8 (2)
C2—C1—C14—C15177.76 (14)C7—C8—C9—C1051.8 (2)
C2—C1—C14—C2062.56 (18)C8—C9—C10—C551.3 (2)
C14—C1—C2—C3173.08 (15)C8—C9—C10—C11175.79 (15)
C14—C1—C2—C1162.58 (18)C5—C10—C11—C252.86 (19)
C2—C1—C17—C16161.68 (17)C5—C10—C11—C12177.97 (15)
C17—C1—C2—C349.7 (2)C9—C10—C11—C2177.16 (14)
C17—C1—C2—C11174.03 (15)C9—C10—C11—C1257.7 (2)
C14—C1—C17—C1634.53 (19)C2—C11—C12—C1353.0 (2)
C17—C1—C14—C13166.97 (15)C10—C11—C12—C13179.01 (15)
C17—C1—C14—C1545.62 (17)C11—C12—C13—C1452.5 (2)
C17—C1—C14—C2069.58 (18)C12—C13—C14—C154.00 (19)
C1—C2—C3—C4146.81 (19)C12—C13—C14—C15163.99 (15)
C1—C2—C11—C10176.38 (13)C12—C13—C14—C2070.28 (18)
C1—C2—C11—C1256.64 (18)C1—C14—C15—O2157.87 (13)
C3—C2—C11—C1049.97 (19)C1—C14—C15—C1639.84 (17)
C3—C2—C11—C12176.95 (15)C13—C14—C15—O286.74 (18)
C11—C2—C3—C423.7 (2)C13—C14—C15—C16155.22 (15)
C2—C3—C4—C50.1 (2)C20—C14—C15—O240.03 (18)
C3—C4—C5—C6179.5 (2)C20—C14—C15—C1678.00 (17)
C3—C4—C5—C103.3 (2)O2—C15—C16—C17142.74 (16)
C4—C5—C6—C7176.97 (19)C14—C15—C16—C1719.8 (2)
C4—C5—C10—C9156.42 (17)C15—C16—C17—C19.0 (2)
C4—C5—C10—C1129.8 (2)O2—C18—C19—Cl1168.34 (12)
C6—C5—C10—C926.4 (2)O3—C18—C19—Cl112.5 (2)
C6—C5—C10—C11152.97 (18)
 

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