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In the title compound, C18H24O2, a derivative of dehydro­abietic acid formed by a Friedel-Crafts reaction between methyl dehydro­abietate and aluminium trichloride, the fused cyclohexane rings exhibit classical chair and half-chair conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024640/ym2011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024640/ym2011Isup2.hkl
Contains datablock I

CCDC reference: 618355

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.072
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.784 0.978 Tmin(prime) and Tmax expected: 0.961 0.977 RR(prime) = 0.815 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.84
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 25.30 From the CIF: _reflns_number_total 1451 Count of symmetry unique reflns 1453 Completeness (_total/calc) 99.86% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: 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 cis-deisopropyldehydroabietate top
Crystal data top
C18H24O2F(000) = 296
Mr = 272.37Dx = 1.229 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ybCell parameters from 3201 reflections
a = 8.459 (2) Åθ = 3.1–25.3°
b = 7.4681 (19) ŵ = 0.08 mm1
c = 11.701 (3) ÅT = 153 K
β = 95.173 (5)°Block, colourless
V = 736.1 (3) Å30.50 × 0.44 × 0.30 mm
Z = 2
Data collection top
Rigaku Mercury
diffractometer
1451 independent reflections
Radiation source: fine-focus sealed tube1436 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 7.31 pixels mm-1θmax = 25.3°, θmin = 3.2°
ω scansh = 910
Absorption correction: multi-scan
(Jacobson, 1998)
k = 88
Tmin = 0.784, Tmax = 0.978l = 1414
7106 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0435P)2 + 0.1277P]
where P = (Fo2 + 2Fc2)/3
1451 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.14 e Å3
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
O10.74489 (16)0.6125 (2)0.50251 (11)0.0334 (3)
O20.93868 (14)0.46742 (19)0.60790 (10)0.0269 (3)
C10.6788 (2)0.4397 (2)0.66822 (14)0.0206 (4)
C20.5115 (2)0.5190 (3)0.64571 (15)0.0258 (4)
H2A0.47710.50940.56280.031*
H2B0.43700.44750.68780.031*
C30.5022 (2)0.7139 (3)0.68206 (15)0.0285 (4)
H3A0.39100.75600.66960.034*
H3B0.56770.78840.63460.034*
C40.5615 (2)0.7344 (3)0.80868 (14)0.0248 (4)
H4A0.48830.66970.85560.030*
H4B0.55830.86280.82950.030*
C50.73203 (19)0.6633 (2)0.83896 (14)0.0198 (4)
C60.74541 (19)0.4659 (2)0.79664 (14)0.0179 (4)
H60.86120.43660.80110.021*
C70.6701 (2)0.3358 (3)0.87732 (15)0.0224 (4)
H7A0.55880.37120.88530.027*
H7B0.66990.21310.84530.027*
C80.7651 (2)0.3396 (2)0.99400 (14)0.0223 (4)
H8A0.71360.26071.04770.027*
H8B0.87320.29280.98650.027*
C90.77667 (19)0.5263 (2)1.04225 (15)0.0211 (4)
C100.7979 (2)0.5498 (3)1.16174 (15)0.0254 (4)
H100.80400.44741.21010.031*
C110.8100 (2)0.7176 (3)1.21071 (15)0.0276 (4)
H110.82480.73061.29170.033*
C120.8002 (2)0.8670 (3)1.14038 (16)0.0262 (4)
H120.80940.98351.17290.031*
C130.7770 (2)0.8460 (3)1.02216 (16)0.0239 (4)
H130.76880.94940.97470.029*
C140.76522 (18)0.6758 (2)0.97074 (14)0.0201 (4)
C150.7872 (2)0.5212 (3)0.58444 (14)0.0233 (4)
C161.0505 (2)0.5344 (3)0.53237 (17)0.0352 (5)
H16A1.00760.51730.45250.053*
H16B1.15090.46930.54620.053*
H16C1.06880.66230.54700.053*
C170.6726 (2)0.2390 (3)0.63520 (15)0.0264 (4)
H17A0.65450.22740.55160.040*
H17B0.58580.18070.67110.040*
H17C0.77340.18170.66200.040*
C180.8531 (2)0.7812 (3)0.78337 (15)0.0248 (4)
H18A0.84900.90330.81370.037*
H18B0.82730.78340.70000.037*
H18C0.96000.73220.80100.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0349 (7)0.0415 (8)0.0239 (6)0.0045 (6)0.0030 (5)0.0107 (6)
O20.0248 (6)0.0308 (7)0.0262 (6)0.0031 (6)0.0089 (5)0.0057 (6)
C10.0216 (8)0.0228 (9)0.0172 (8)0.0004 (7)0.0011 (6)0.0017 (7)
C20.0215 (8)0.0325 (10)0.0228 (8)0.0009 (8)0.0015 (6)0.0020 (8)
C30.0241 (8)0.0334 (11)0.0272 (9)0.0097 (8)0.0025 (7)0.0004 (9)
C40.0254 (9)0.0237 (10)0.0250 (8)0.0068 (7)0.0009 (7)0.0011 (7)
C50.0204 (8)0.0191 (9)0.0197 (8)0.0001 (7)0.0009 (6)0.0012 (7)
C60.0171 (8)0.0187 (9)0.0178 (8)0.0006 (7)0.0019 (6)0.0001 (7)
C70.0246 (8)0.0191 (8)0.0237 (8)0.0022 (7)0.0041 (7)0.0001 (7)
C80.0270 (9)0.0201 (9)0.0203 (9)0.0000 (8)0.0052 (7)0.0036 (7)
C90.0166 (8)0.0251 (10)0.0220 (8)0.0007 (7)0.0034 (6)0.0001 (8)
C100.0253 (9)0.0297 (11)0.0213 (9)0.0050 (8)0.0017 (7)0.0033 (8)
C110.0254 (8)0.0359 (11)0.0213 (8)0.0036 (9)0.0005 (7)0.0036 (8)
C120.0243 (9)0.0246 (10)0.0293 (9)0.0015 (8)0.0010 (7)0.0077 (8)
C130.0238 (9)0.0222 (9)0.0256 (9)0.0009 (8)0.0025 (7)0.0015 (8)
C140.0166 (7)0.0222 (9)0.0219 (8)0.0008 (7)0.0038 (6)0.0006 (7)
C150.0266 (9)0.0231 (9)0.0204 (8)0.0015 (7)0.0029 (7)0.0024 (7)
C160.0324 (10)0.0371 (12)0.0384 (10)0.0019 (9)0.0171 (8)0.0092 (10)
C170.0332 (9)0.0242 (10)0.0217 (8)0.0036 (8)0.0016 (7)0.0045 (8)
C180.0289 (9)0.0207 (8)0.0252 (8)0.0033 (8)0.0042 (7)0.0023 (7)
Geometric parameters (Å, º) top
O1—C151.204 (2)C7—H7B0.9900
O2—C151.347 (2)C8—C91.504 (3)
O2—C161.441 (2)C8—H8A0.9900
C1—C151.527 (2)C8—H8B0.9900
C1—C21.535 (2)C9—C141.394 (2)
C1—C171.548 (3)C9—C101.404 (2)
C1—C61.569 (2)C10—C111.378 (3)
C2—C31.521 (3)C10—H100.9500
C2—H2A0.9900C11—C121.385 (3)
C2—H2B0.9900C11—H110.9500
C3—C41.529 (2)C12—C131.388 (3)
C3—H3A0.9900C12—H120.9500
C3—H3B0.9900C13—C141.406 (3)
C4—C51.548 (2)C13—H130.9500
C4—H4A0.9900C16—H16A0.9800
C4—H4B0.9900C16—H16B0.9800
C5—C181.539 (2)C16—H16C0.9800
C5—C141.545 (2)C17—H17A0.9800
C5—C61.562 (2)C17—H17B0.9800
C6—C71.533 (2)C17—H17C0.9800
C6—H61.0000C18—H18A0.9800
C7—C81.521 (2)C18—H18B0.9800
C7—H7A0.9900C18—H18C0.9800
C15—O2—C16115.86 (15)C9—C8—H8A109.3
C15—C1—C2109.48 (15)C7—C8—H8A109.3
C15—C1—C17103.58 (14)C9—C8—H8B109.3
C2—C1—C17108.69 (15)C7—C8—H8B109.3
C15—C1—C6112.38 (13)H8A—C8—H8B108.0
C2—C1—C6111.23 (13)C14—C9—C10119.54 (16)
C17—C1—C6111.17 (14)C14—C9—C8121.25 (14)
C3—C2—C1113.05 (15)C10—C9—C8119.20 (16)
C3—C2—H2A109.0C11—C10—C9121.73 (17)
C1—C2—H2A109.0C11—C10—H10119.1
C3—C2—H2B109.0C9—C10—H10119.1
C1—C2—H2B109.0C10—C11—C12119.19 (15)
H2A—C2—H2B107.8C10—C11—H11120.4
C2—C3—C4110.26 (16)C12—C11—H11120.4
C2—C3—H3A109.6C11—C12—C13119.76 (18)
C4—C3—H3A109.6C11—C12—H12120.1
C2—C3—H3B109.6C13—C12—H12120.1
C4—C3—H3B109.6C12—C13—C14121.79 (18)
H3A—C3—H3B108.1C12—C13—H13119.1
C3—C4—C5113.89 (14)C14—C13—H13119.1
C3—C4—H4A108.8C9—C14—C13117.98 (15)
C5—C4—H4A108.8C9—C14—C5123.17 (15)
C3—C4—H4B108.8C13—C14—C5118.78 (15)
C5—C4—H4B108.8O1—C15—O2122.66 (16)
H4A—C4—H4B107.7O1—C15—C1125.76 (16)
C18—C5—C14108.61 (13)O2—C15—C1111.41 (14)
C18—C5—C4110.40 (14)O2—C16—H16A109.5
C14—C5—C4106.81 (13)O2—C16—H16B109.5
C18—C5—C6109.65 (13)H16A—C16—H16B109.5
C14—C5—C6111.20 (13)O2—C16—H16C109.5
C4—C5—C6110.12 (13)H16A—C16—H16C109.5
C7—C6—C5110.91 (13)H16B—C16—H16C109.5
C7—C6—C1112.18 (14)C1—C17—H17A109.5
C5—C6—C1113.04 (13)C1—C17—H17B109.5
C7—C6—H6106.8H17A—C17—H17B109.5
C5—C6—H6106.8C1—C17—H17C109.5
C1—C6—H6106.8H17A—C17—H17C109.5
C8—C7—C6108.99 (14)H17B—C17—H17C109.5
C8—C7—H7A109.9C5—C18—H18A109.5
C6—C7—H7A109.9C5—C18—H18B109.5
C8—C7—H7B109.9H18A—C18—H18B109.5
C6—C7—H7B109.9C5—C18—H18C109.5
H7A—C7—H7B108.3H18A—C18—H18C109.5
C9—C8—C7111.46 (15)H18B—C18—H18C109.5
C15—C1—C2—C370.93 (18)C14—C9—C10—C110.9 (3)
C17—C1—C2—C3176.57 (14)C8—C9—C10—C11179.70 (17)
C6—C1—C2—C353.9 (2)C9—C10—C11—C120.3 (3)
C1—C2—C3—C456.20 (19)C10—C11—C12—C130.6 (3)
C2—C3—C4—C556.3 (2)C11—C12—C13—C141.0 (3)
C3—C4—C5—C1868.0 (2)C10—C9—C14—C130.6 (2)
C3—C4—C5—C14174.07 (16)C8—C9—C14—C13179.92 (17)
C3—C4—C5—C653.20 (19)C10—C9—C14—C5176.28 (15)
C18—C5—C6—C7161.16 (14)C8—C9—C14—C53.1 (2)
C14—C5—C6—C741.03 (18)C12—C13—C14—C90.4 (2)
C4—C5—C6—C777.17 (16)C12—C13—C14—C5177.35 (15)
C18—C5—C6—C171.85 (16)C18—C5—C14—C9131.45 (16)
C14—C5—C6—C1168.02 (13)C4—C5—C14—C9109.47 (17)
C4—C5—C6—C149.82 (17)C6—C5—C14—C910.7 (2)
C15—C1—C6—C7161.26 (15)C18—C5—C14—C1351.7 (2)
C2—C1—C6—C775.60 (19)C4—C5—C14—C1367.35 (19)
C17—C1—C6—C745.67 (19)C6—C5—C14—C13172.48 (15)
C15—C1—C6—C572.43 (17)C16—O2—C15—O13.5 (3)
C2—C1—C6—C550.71 (18)C16—O2—C15—C1178.94 (16)
C17—C1—C6—C5171.98 (14)C2—C1—C15—O110.2 (3)
C5—C6—C7—C865.16 (18)C17—C1—C15—O1105.5 (2)
C1—C6—C7—C8167.38 (14)C6—C1—C15—O1134.36 (19)
C6—C7—C8—C956.00 (18)C2—C1—C15—O2174.45 (14)
C7—C8—C9—C1425.8 (2)C17—C1—C15—O269.76 (17)
C7—C8—C9—C10153.52 (15)C6—C1—C15—O250.3 (2)
 

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