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The structure of the title compound (systematic name: methyl 6-chloro-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro­phenanthrene-1-carboxyl­ate), C21H29ClO2, has been determined by X-ray diffraction and is compared with the structures of methyl 12-acetyl­dehydro­abietate and methyl dehydro­abietate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045004/wk2031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045004/wk2031Isup2.hkl
Contains datablock I

CCDC reference: 604686

Key indicators

  • Single-crystal X-ray study
  • T = 163 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.081
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



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 25.35 From the CIF: _reflns_number_total 3282 Count of symmetry unique reflns 1885 Completeness (_total/calc) 174.11% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1397 Fraction of Friedel pairs measured 0.741 Are heavy atom types Z>Si present yes 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 C14 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

methyl 6-chloro-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene- 1-carboxylate top
Crystal data top
C21H29ClO2F(000) = 752
Mr = 348.89Dx = 1.237 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 3656 reflections
a = 13.6507 (17) Åθ = 3.1–25.3°
b = 6.0856 (6) ŵ = 0.21 mm1
c = 23.120 (3) ÅT = 163 K
β = 102.760 (16)°Platelet, colourless
V = 1873.2 (4) Å30.56 × 0.41 × 0.06 mm
Z = 4
Data collection top
Rigaku Mercury
diffractometer
3282 independent reflections
Radiation source: fine-focus sealed tube3079 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.1°
ω scansh = 1615
Absorption correction: multi-scan
(Jacobson, 1998)
k = 76
Tmin = 0.856, Tmax = 0.987l = 2727
9174 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)] = 0.036H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0334P)2 + 0.9195P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3282 reflectionsΔρmax = 0.19 e Å3
222 parametersΔρmin = 0.17 e Å3
1 restraintAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
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
Cl10.53162 (4)0.49514 (10)0.91824 (2)0.03557 (16)
O10.66971 (14)0.1660 (3)0.55486 (8)0.0413 (4)
O20.64227 (12)0.1780 (2)0.57863 (7)0.0308 (4)
C10.55802 (15)0.2461 (4)0.82713 (9)0.0219 (4)
H10.48810.21890.82180.026*
C20.60639 (16)0.3760 (3)0.87397 (9)0.0227 (5)
C30.70896 (15)0.4187 (3)0.88520 (9)0.0226 (5)
C40.75951 (15)0.3234 (4)0.84577 (9)0.0244 (5)
H40.82980.34780.85190.029*
C50.71356 (15)0.1936 (4)0.79754 (9)0.0226 (5)
C60.61047 (14)0.1546 (3)0.78759 (9)0.0191 (4)
C70.55540 (13)0.0072 (4)0.73659 (8)0.0184 (4)
C80.61799 (13)0.0085 (4)0.68807 (8)0.0189 (4)
H80.62410.16740.67840.023*
C90.72577 (15)0.0661 (4)0.71344 (9)0.0245 (5)
H9A0.72550.21060.73310.029*
H9B0.76200.08210.68100.029*
C100.77859 (15)0.1031 (4)0.75811 (10)0.0279 (5)
H10A0.83900.03460.78330.034*
H10B0.80130.22630.73640.034*
C110.45038 (14)0.0987 (4)0.70904 (9)0.0218 (5)
H11A0.40720.08280.73800.026*
H11B0.45630.25750.70120.026*
C120.39958 (14)0.0155 (4)0.65137 (8)0.0249 (4)
H12A0.38760.17170.65960.030*
H12B0.33360.05420.63540.030*
C130.46347 (14)0.0020 (4)0.60542 (8)0.0231 (4)
H13A0.47000.15380.59460.028*
H13B0.42910.08140.56920.028*
C140.56911 (15)0.1002 (3)0.62767 (9)0.0207 (5)
C150.76249 (16)0.5658 (4)0.93530 (9)0.0281 (5)
H150.72280.56440.96680.034*
C160.76360 (18)0.8026 (4)0.91276 (10)0.0352 (6)
H16A0.79670.80670.87920.053*
H16B0.80030.89650.94470.053*
H16C0.69450.85600.89990.053*
C170.86868 (17)0.4894 (5)0.96343 (10)0.0408 (6)
H17A0.86740.33350.97380.061*
H17B0.89490.57560.99930.061*
H17C0.91200.51010.93520.061*
C180.54484 (15)0.2213 (4)0.76417 (9)0.0243 (5)
H18A0.51470.20420.79870.037*
H18B0.61130.28900.77660.037*
H18C0.50180.31530.73470.037*
C190.56428 (17)0.3530 (3)0.62907 (10)0.0288 (5)
H19A0.54330.40920.58850.043*
H19B0.51570.39890.65220.043*
H19C0.63080.41170.64740.043*
C200.63266 (15)0.0388 (4)0.58337 (9)0.0232 (5)
C210.70048 (17)0.2544 (4)0.53759 (9)0.0319 (5)
H21A0.76920.19780.54950.048*
H21B0.70190.41540.53770.048*
H21C0.66990.20180.49760.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0331 (3)0.0447 (4)0.0311 (3)0.0004 (3)0.0116 (2)0.0103 (3)
O10.0620 (12)0.0260 (9)0.0471 (10)0.0005 (8)0.0359 (9)0.0046 (8)
O20.0455 (10)0.0197 (8)0.0345 (9)0.0049 (7)0.0245 (8)0.0018 (7)
C10.0199 (10)0.0235 (10)0.0227 (10)0.0022 (9)0.0059 (8)0.0003 (9)
C20.0262 (11)0.0231 (12)0.0210 (11)0.0032 (9)0.0100 (9)0.0023 (9)
C30.0260 (11)0.0222 (11)0.0180 (10)0.0021 (9)0.0013 (9)0.0048 (9)
C40.0188 (10)0.0275 (12)0.0257 (11)0.0052 (9)0.0026 (8)0.0034 (10)
C50.0211 (10)0.0248 (12)0.0220 (10)0.0001 (9)0.0051 (8)0.0042 (9)
C60.0198 (10)0.0197 (11)0.0184 (10)0.0006 (9)0.0054 (8)0.0034 (9)
C70.0163 (9)0.0177 (10)0.0212 (9)0.0030 (9)0.0041 (7)0.0001 (10)
C80.0188 (9)0.0178 (11)0.0208 (9)0.0008 (10)0.0057 (7)0.0007 (10)
C90.0199 (10)0.0286 (13)0.0271 (11)0.0039 (9)0.0096 (9)0.0012 (9)
C100.0160 (10)0.0389 (14)0.0293 (12)0.0016 (10)0.0058 (9)0.0002 (10)
C110.0180 (10)0.0241 (11)0.0241 (11)0.0004 (9)0.0060 (8)0.0001 (9)
C120.0177 (9)0.0304 (12)0.0254 (10)0.0007 (10)0.0022 (8)0.0025 (10)
C130.0237 (10)0.0254 (11)0.0190 (9)0.0039 (10)0.0018 (8)0.0022 (10)
C140.0237 (11)0.0160 (10)0.0226 (11)0.0010 (9)0.0057 (9)0.0014 (8)
C150.0322 (12)0.0298 (13)0.0213 (11)0.0052 (10)0.0041 (9)0.0015 (9)
C160.0426 (14)0.0291 (14)0.0314 (12)0.0065 (12)0.0025 (11)0.0062 (11)
C170.0375 (13)0.0405 (14)0.0368 (13)0.0027 (13)0.0080 (10)0.0033 (13)
C180.0258 (11)0.0217 (12)0.0266 (11)0.0034 (10)0.0081 (9)0.0001 (9)
C190.0380 (13)0.0173 (11)0.0336 (13)0.0011 (10)0.0134 (10)0.0015 (10)
C200.0256 (11)0.0232 (13)0.0208 (10)0.0038 (10)0.0052 (8)0.0034 (10)
C210.0420 (13)0.0316 (13)0.0255 (11)0.0126 (11)0.0149 (10)0.0016 (10)
Geometric parameters (Å, º) top
Cl1—C21.754 (2)C11—H11B0.9900
O1—C201.199 (2)C12—C131.518 (3)
O2—C201.333 (3)C12—H12A0.9900
O2—C211.442 (2)C12—H12B0.9900
C1—C21.385 (3)C13—C141.541 (3)
C1—C61.396 (3)C13—H13A0.9900
C1—H10.9500C13—H13B0.9900
C2—C31.391 (3)C14—C201.528 (3)
C3—C41.386 (3)C14—C191.540 (3)
C3—C151.518 (3)C15—C171.524 (3)
C4—C51.397 (3)C15—C161.533 (3)
C4—H40.9500C15—H151.0000
C5—C61.395 (3)C16—H16A0.9800
C5—C101.510 (3)C16—H16B0.9800
C6—C71.539 (3)C16—H16C0.9800
C7—C111.539 (3)C17—H17A0.9800
C7—C181.550 (3)C17—H17B0.9800
C7—C81.553 (2)C17—H17C0.9800
C8—C91.528 (3)C18—H18A0.9800
C8—C141.556 (3)C18—H18B0.9800
C8—H81.0000C18—H18C0.9800
C9—C101.522 (3)C19—H19A0.9800
C9—H9A0.9900C19—H19B0.9800
C9—H9B0.9900C19—H19C0.9800
C10—H10A0.9900C21—H21A0.9800
C10—H10B0.9900C21—H21B0.9800
C11—C121.527 (3)C21—H21C0.9800
C11—H11A0.9900
C20—O2—C21116.85 (17)C11—C12—H12B109.3
C2—C1—C6121.01 (19)H12A—C12—H12B108.0
C2—C1—H1119.5C12—C13—C14112.67 (16)
C6—C1—H1119.5C12—C13—H13A109.1
C1—C2—C3122.62 (19)C14—C13—H13A109.1
C1—C2—Cl1116.99 (16)C12—C13—H13B109.1
C3—C2—Cl1120.35 (16)C14—C13—H13B109.1
C4—C3—C2115.20 (18)H13A—C13—H13B107.8
C4—C3—C15121.54 (19)C20—C14—C19106.97 (17)
C2—C3—C15123.22 (19)C20—C14—C13108.03 (16)
C3—C4—C5124.10 (19)C19—C14—C13110.69 (19)
C3—C4—H4118.0C20—C14—C8107.64 (16)
C5—C4—H4118.0C19—C14—C8114.68 (18)
C6—C5—C4119.12 (18)C13—C14—C8108.59 (16)
C6—C5—C10122.97 (18)C3—C15—C17113.4 (2)
C4—C5—C10117.91 (17)C3—C15—C16109.52 (17)
C5—C6—C1117.94 (19)C17—C15—C16110.6 (2)
C5—C6—C7122.00 (17)C3—C15—H15107.7
C1—C6—C7120.01 (17)C17—C15—H15107.7
C11—C7—C6111.04 (18)C16—C15—H15107.7
C11—C7—C18109.41 (16)C15—C16—H16A109.5
C6—C7—C18106.38 (15)C15—C16—H16B109.5
C11—C7—C8108.05 (15)H16A—C16—H16B109.5
C6—C7—C8107.26 (15)C15—C16—H16C109.5
C18—C7—C8114.70 (18)H16A—C16—H16C109.5
C9—C8—C7110.97 (15)H16B—C16—H16C109.5
C9—C8—C14113.82 (16)C15—C17—H17A109.5
C7—C8—C14116.79 (15)C15—C17—H17B109.5
C9—C8—H8104.6H17A—C17—H17B109.5
C7—C8—H8104.6C15—C17—H17C109.5
C14—C8—H8104.6H17A—C17—H17C109.5
C10—C9—C8109.34 (17)H17B—C17—H17C109.5
C10—C9—H9A109.8C7—C18—H18A109.5
C8—C9—H9A109.8C7—C18—H18B109.5
C10—C9—H9B109.8H18A—C18—H18B109.5
C8—C9—H9B109.8C7—C18—H18C109.5
H9A—C9—H9B108.3H18A—C18—H18C109.5
C5—C10—C9113.76 (17)H18B—C18—H18C109.5
C5—C10—H10A108.8C14—C19—H19A109.5
C9—C10—H10A108.8C14—C19—H19B109.5
C5—C10—H10B108.8H19A—C19—H19B109.5
C9—C10—H10B108.8C14—C19—H19C109.5
H10A—C10—H10B107.7H19A—C19—H19C109.5
C12—C11—C7113.49 (17)H19B—C19—H19C109.5
C12—C11—H11A108.9O1—C20—O2122.19 (19)
C7—C11—H11A108.9O1—C20—C14125.58 (19)
C12—C11—H11B108.9O2—C20—C14112.23 (16)
C7—C11—H11B108.9O2—C21—H21A109.5
H11A—C11—H11B107.7O2—C21—H21B109.5
C13—C12—C11111.46 (16)H21A—C21—H21B109.5
C13—C12—H12A109.3O2—C21—H21C109.5
C11—C12—H12A109.3H21A—C21—H21C109.5
C13—C12—H12B109.3H21B—C21—H21C109.5
C6—C1—C2—C31.5 (3)C6—C5—C10—C910.2 (3)
C6—C1—C2—Cl1176.43 (17)C4—C5—C10—C9170.26 (19)
C1—C2—C3—C40.5 (3)C8—C9—C10—C540.7 (3)
Cl1—C2—C3—C4177.30 (16)C6—C7—C11—C12169.48 (16)
C1—C2—C3—C15178.2 (2)C18—C7—C11—C1273.4 (2)
Cl1—C2—C3—C150.4 (3)C8—C7—C11—C1252.1 (2)
C2—C3—C4—C50.3 (3)C7—C11—C12—C1357.1 (2)
C15—C3—C4—C5177.4 (2)C11—C12—C13—C1457.1 (3)
C3—C4—C5—C60.2 (3)C12—C13—C14—C20169.25 (18)
C3—C4—C5—C10179.3 (2)C12—C13—C14—C1973.9 (2)
C4—C5—C6—C10.7 (3)C12—C13—C14—C852.8 (2)
C10—C5—C6—C1179.8 (2)C9—C8—C14—C2060.2 (2)
C4—C5—C6—C7177.96 (19)C7—C8—C14—C20168.44 (17)
C10—C5—C6—C72.5 (3)C9—C8—C14—C1958.7 (2)
C2—C1—C6—C51.5 (3)C7—C8—C14—C1972.7 (2)
C2—C1—C6—C7178.83 (19)C9—C8—C14—C13176.89 (18)
C5—C6—C7—C11142.74 (19)C7—C8—C14—C1351.7 (2)
C1—C6—C7—C1140.1 (3)C4—C3—C15—C1737.6 (3)
C5—C6—C7—C1898.3 (2)C2—C3—C15—C17144.9 (2)
C1—C6—C7—C1878.9 (2)C4—C3—C15—C1686.5 (3)
C5—C6—C7—C824.9 (3)C2—C3—C15—C1691.0 (2)
C1—C6—C7—C8157.92 (18)C21—O2—C20—O10.5 (3)
C11—C7—C8—C9176.19 (18)C21—O2—C20—C14179.62 (16)
C6—C7—C8—C956.4 (2)C19—C14—C20—O11.1 (3)
C18—C7—C8—C961.5 (2)C13—C14—C20—O1118.1 (2)
C11—C7—C8—C1451.1 (2)C8—C14—C20—O1124.8 (2)
C6—C7—C8—C14170.88 (17)C19—C14—C20—O2179.81 (18)
C18—C7—C8—C1471.2 (2)C13—C14—C20—O261.0 (2)
C7—C8—C9—C1066.5 (2)C8—C14—C20—O256.1 (2)
C14—C8—C9—C10159.32 (17)
 

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