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The title compound, C27H35NO [systematic name: (1R,4aS,10aR)-7-iso­propyl-N,1,4a-trimethyl-N-phenyl-1,2,3,4,4a,9,10,10a-octa­hydro­phenanthrene-1-carboxamide], has been syn­thesized from dehydro­abietic acid. The two cyclo­hexane rings form a trans ring junction with classical chair and half-boat conformations, each somewhat deformed towards a half-chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043935/kj2035sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043935/kj2035Isup2.hkl
Contains datablock I

CCDC reference: 627959

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.064
  • wR factor = 0.179
  • Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 26.99 From the CIF: _reflns_number_total 2680 Count of symmetry unique reflns 2688 Completeness (_total/calc) 99.70% 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 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 C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Dehydroabietic acid N-methyl-anilide top
Crystal data top
C27H35NOF(000) = 424
Mr = 389.56Dx = 1.145 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.460 (2) ÅCell parameters from 25 reflections
b = 6.7200 (13) Åθ = 10–13°
c = 16.086 (3) ŵ = 0.07 mm1
β = 91.30 (3)°T = 293 K
V = 1130.4 (4) Å3Block, colourless
Z = 20.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.0°, θmin = 1.3°
ω/2θ scansh = 1313
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
k = 80
Tmin = 0.980, Tmax = 0.993l = 200
2771 measured reflections3 standard reflections every 200 reflections
2680 independent reflections intensity decay: none
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2 + 0.2P]
where P = (Fo2 + 2Fc2)/3
2680 reflections(Δ/σ)max = 0.025
262 parametersΔρmax = 0.20 e Å3
22 restraintsΔρmin = 0.24 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
N0.6719 (3)0.4114 (5)0.44181 (19)0.0474 (8)
O0.5173 (4)0.1956 (7)0.4171 (2)0.0931 (15)
C10.1332 (5)0.1796 (12)0.1022 (5)0.116 (2)
H1A0.13550.05540.07270.173*
H1B0.15080.15670.15970.173*
H1C0.19650.26790.07870.173*
C20.0070 (6)0.4631 (9)0.1400 (4)0.0878 (17)
H2A0.06540.54610.12690.132*
H2B0.01140.43950.19890.132*
H2C0.08380.52820.12310.132*
C30.0068 (4)0.2691 (8)0.0952 (3)0.0705 (14)
H3A0.00020.30270.03620.085*
C40.1045 (4)0.1286 (7)0.1137 (3)0.0602 (12)
C50.2039 (4)0.1160 (8)0.0604 (3)0.0632 (12)
H5A0.20200.19080.01180.076*
C60.3069 (4)0.0056 (8)0.0776 (3)0.0607 (12)
H6A0.37210.01220.03940.073*
C70.3176 (4)0.1198 (6)0.1502 (2)0.0461 (9)
C80.4325 (4)0.2568 (6)0.1658 (2)0.0467 (9)
C90.5551 (4)0.1616 (7)0.1334 (3)0.0580 (12)
H9A0.56250.02690.15460.070*
H9B0.54980.15460.07320.070*
C100.6731 (4)0.2794 (9)0.1596 (3)0.0623 (12)
H10A0.66670.41330.13740.075*
H10B0.74830.21740.13680.075*
C110.6877 (4)0.2891 (9)0.2538 (3)0.0584 (12)
H11A0.76410.36440.26830.070*
H11B0.69900.15530.27540.070*
C120.5726 (4)0.3855 (7)0.2956 (2)0.0475 (10)
C130.4474 (3)0.2856 (6)0.2608 (2)0.0429 (9)
H13A0.45050.14990.28310.051*
C140.3263 (4)0.3737 (7)0.2956 (3)0.0542 (10)
H14A0.30420.49530.26620.065*
H14B0.33980.40560.35400.065*
C150.2177 (4)0.2233 (8)0.2858 (3)0.0609 (12)
H15A0.22340.12950.33160.073*
H15B0.13700.29330.28990.073*
C160.2168 (4)0.1087 (7)0.2054 (2)0.0493 (10)
C170.1125 (4)0.0161 (8)0.1862 (3)0.0590 (11)
H17A0.04610.02380.22350.071*
C180.4052 (5)0.4488 (8)0.1145 (3)0.0643 (13)
H18A0.39740.41570.05650.097*
H18B0.47430.54120.12290.097*
H18C0.32700.50810.13240.097*
C190.5709 (5)0.6125 (7)0.2822 (3)0.0629 (13)
H19A0.64890.66910.30410.094*
H19B0.49960.66920.31030.094*
H19C0.56320.64070.22380.094*
C200.5842 (4)0.3286 (7)0.3890 (2)0.0503 (10)
C210.6704 (4)0.3456 (8)0.5290 (2)0.0550 (11)
H21A0.60620.24490.53510.083*
H21B0.65140.45670.56410.083*
H21C0.75250.29200.54460.083*
C220.7655 (4)0.5628 (6)0.4258 (2)0.0432 (9)
C230.8851 (4)0.5126 (7)0.3991 (3)0.0528 (10)
H23A0.90430.38040.38770.063*
C240.9769 (4)0.6574 (9)0.3893 (3)0.0623 (13)
H24A1.05760.62230.37110.075*
C250.9499 (5)0.8533 (8)0.4062 (3)0.0651 (13)
H25A1.01130.95120.39820.078*
C260.8316 (5)0.9029 (8)0.4348 (3)0.0694 (13)
H26A0.81381.03490.44750.083*
C270.7388 (4)0.7603 (7)0.4451 (3)0.0586 (12)
H27A0.65890.79550.46470.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0506 (17)0.0465 (19)0.0454 (17)0.0047 (17)0.0030 (14)0.0010 (16)
O0.105 (3)0.114 (4)0.0598 (19)0.068 (3)0.0170 (17)0.034 (2)
C10.074 (3)0.086 (4)0.186 (6)0.004 (3)0.015 (4)0.013 (5)
C20.087 (3)0.067 (3)0.108 (4)0.025 (3)0.021 (3)0.018 (3)
C30.059 (2)0.062 (3)0.090 (3)0.012 (2)0.016 (2)0.006 (3)
C40.057 (2)0.046 (3)0.076 (3)0.007 (2)0.021 (2)0.007 (2)
C50.066 (3)0.060 (3)0.063 (3)0.010 (3)0.007 (2)0.007 (2)
C60.062 (2)0.068 (3)0.052 (2)0.017 (3)0.0036 (19)0.005 (2)
C70.050 (2)0.039 (2)0.049 (2)0.0056 (19)0.0026 (17)0.0044 (19)
C80.052 (2)0.043 (2)0.045 (2)0.0114 (19)0.0044 (16)0.0026 (18)
C90.061 (2)0.060 (3)0.053 (2)0.013 (2)0.0108 (19)0.009 (2)
C100.051 (2)0.075 (3)0.062 (3)0.010 (2)0.0137 (18)0.010 (3)
C110.045 (2)0.071 (3)0.059 (2)0.015 (2)0.0021 (17)0.002 (2)
C120.049 (2)0.045 (2)0.048 (2)0.015 (2)0.0000 (17)0.0026 (19)
C130.0452 (19)0.041 (2)0.0423 (19)0.0094 (18)0.0021 (15)0.0049 (18)
C140.058 (2)0.052 (3)0.053 (2)0.004 (2)0.0040 (18)0.003 (2)
C150.046 (2)0.079 (4)0.058 (2)0.008 (2)0.0064 (18)0.003 (2)
C160.052 (2)0.047 (2)0.048 (2)0.005 (2)0.0039 (17)0.007 (2)
C170.050 (2)0.059 (3)0.068 (3)0.007 (2)0.0013 (19)0.013 (2)
C180.077 (3)0.057 (3)0.059 (3)0.017 (3)0.007 (2)0.013 (2)
C190.084 (3)0.046 (3)0.059 (3)0.021 (2)0.004 (2)0.001 (2)
C200.050 (2)0.054 (3)0.047 (2)0.017 (2)0.0018 (17)0.003 (2)
C210.059 (2)0.060 (3)0.046 (2)0.002 (2)0.0027 (17)0.002 (2)
C220.043 (2)0.042 (2)0.0438 (19)0.0047 (18)0.0004 (16)0.0071 (17)
C230.050 (2)0.045 (2)0.063 (2)0.002 (2)0.0008 (19)0.008 (2)
C240.039 (2)0.079 (4)0.069 (3)0.009 (2)0.0031 (19)0.014 (3)
C250.065 (3)0.057 (3)0.073 (3)0.025 (3)0.003 (2)0.004 (3)
C260.078 (3)0.040 (2)0.090 (3)0.007 (3)0.001 (3)0.017 (3)
C270.053 (2)0.054 (3)0.069 (3)0.002 (2)0.005 (2)0.021 (2)
Geometric parameters (Å, º) top
N—C201.355 (5)C12—C191.541 (7)
N—C221.440 (5)C12—C201.551 (5)
N—C211.471 (5)C12—C131.565 (5)
O—C201.228 (5)C13—C141.518 (5)
C1—C31.459 (8)C13—H13A0.9800
C1—H1A0.9600C14—C151.526 (6)
C1—H1B0.9600C14—H14A0.9700
C1—H1C0.9600C14—H14B0.9700
C2—C31.494 (8)C15—C161.505 (6)
C2—H2A0.9600C15—H15A0.9700
C2—H2B0.9600C15—H15B0.9700
C2—H2C0.9600C16—C171.405 (6)
C3—C41.523 (6)C17—H17A0.9300
C3—H3A0.9800C18—H18A0.9600
C4—C51.366 (6)C18—H18B0.9600
C4—C171.391 (7)C18—H18C0.9600
C5—C61.375 (6)C19—H19A0.9600
C5—H5A0.9300C19—H19B0.9600
C6—C71.399 (6)C19—H19C0.9600
C6—H6A0.9300C21—H21A0.9600
C7—C161.396 (5)C21—H21B0.9600
C7—C81.531 (5)C21—H21C0.9600
C8—C91.534 (6)C22—C231.374 (5)
C8—C131.545 (5)C22—C271.393 (6)
C8—C181.554 (6)C23—C241.378 (6)
C9—C101.518 (6)C23—H23A0.9300
C9—H9A0.9700C24—C251.375 (8)
C9—H9B0.9700C24—H24A0.9300
C10—C111.521 (6)C25—C261.371 (7)
C10—H10A0.9700C25—H25A0.9300
C10—H10B0.9700C26—C271.377 (6)
C11—C121.535 (6)C26—H26A0.9300
C11—H11A0.9700C27—H27A0.9300
C11—H11B0.9700
C20—N—C22129.1 (3)C14—C13—C8110.4 (3)
C20—N—C21116.9 (3)C14—C13—C12113.5 (3)
C22—N—C21113.9 (3)C8—C13—C12118.2 (3)
C3—C1—H1A109.5C14—C13—H13A104.3
C3—C1—H1B109.5C8—C13—H13A104.3
H1A—C1—H1B109.5C12—C13—H13A104.3
C3—C1—H1C109.5C13—C14—C15109.2 (4)
H1A—C1—H1C109.5C13—C14—H14A109.8
H1B—C1—H1C109.5C15—C14—H14A109.8
C3—C2—H2A109.5C13—C14—H14B109.8
C3—C2—H2B109.5C15—C14—H14B109.8
H2A—C2—H2B109.5H14A—C14—H14B108.3
C3—C2—H2C109.5C16—C15—C14114.7 (3)
H2A—C2—H2C109.5C16—C15—H15A108.6
H2B—C2—H2C109.5C14—C15—H15A108.6
C1—C3—C2113.6 (5)C16—C15—H15B108.6
C1—C3—C4114.8 (5)C14—C15—H15B108.6
C2—C3—C4112.4 (4)H15A—C15—H15B107.6
C1—C3—H3A104.9C7—C16—C17119.1 (4)
C2—C3—H3A104.9C7—C16—C15122.0 (4)
C4—C3—H3A104.9C17—C16—C15119.0 (4)
C5—C4—C17117.4 (4)C4—C17—C16122.8 (4)
C5—C4—C3120.4 (5)C4—C17—H17A118.6
C17—C4—C3122.1 (4)C16—C17—H17A118.6
C4—C5—C6121.0 (4)C8—C18—H18A109.5
C4—C5—H5A119.5C8—C18—H18B109.5
C6—C5—H5A119.5H18A—C18—H18B109.5
C5—C6—C7122.8 (4)C8—C18—H18C109.5
C5—C6—H6A118.6H18A—C18—H18C109.5
C7—C6—H6A118.6H18B—C18—H18C109.5
C16—C7—C6117.0 (4)C12—C19—H19A109.5
C16—C7—C8122.0 (4)C12—C19—H19B109.5
C6—C7—C8121.0 (3)H19A—C19—H19B109.5
C7—C8—C9110.7 (3)C12—C19—H19C109.5
C7—C8—C13107.4 (3)H19A—C19—H19C109.5
C9—C8—C13108.8 (3)H19B—C19—H19C109.5
C7—C8—C18106.1 (3)O—C20—N116.8 (4)
C9—C8—C18108.1 (3)O—C20—C12120.2 (4)
C13—C8—C18115.7 (4)N—C20—C12122.9 (3)
C10—C9—C8111.6 (4)N—C21—H21A109.5
C10—C9—H9A109.3N—C21—H21B109.5
C8—C9—H9A109.3H21A—C21—H21B109.5
C10—C9—H9B109.3N—C21—H21C109.5
C8—C9—H9B109.3H21A—C21—H21C109.5
H9A—C9—H9B108.0H21B—C21—H21C109.5
C9—C10—C11111.2 (4)C23—C22—C27119.5 (4)
C9—C10—H10A109.4C23—C22—N120.7 (4)
C11—C10—H10A109.4C27—C22—N119.5 (3)
C9—C10—H10B109.4C22—C23—C24120.2 (4)
C11—C10—H10B109.4C22—C23—H23A119.9
H10A—C10—H10B108.0C24—C23—H23A119.9
C10—C11—C12113.1 (4)C25—C24—C23120.5 (4)
C10—C11—H11A108.9C25—C24—H24A119.8
C12—C11—H11A108.9C23—C24—H24A119.8
C10—C11—H11B108.9C26—C25—C24119.3 (4)
C12—C11—H11B108.9C26—C25—H25A120.3
H11A—C11—H11B107.8C24—C25—H25A120.3
C11—C12—C19111.3 (4)C25—C26—C27121.0 (5)
C11—C12—C20106.0 (3)C25—C26—H26A119.5
C19—C12—C20112.4 (4)C27—C26—H26A119.5
C11—C12—C13108.7 (3)C26—C27—C22119.4 (4)
C19—C12—C13111.5 (4)C26—C27—H27A120.3
C20—C12—C13106.7 (3)C22—C27—H27A120.3
C1—C3—C4—C5131.1 (6)C8—C13—C14—C1566.1 (4)
C2—C3—C4—C597.0 (6)C12—C13—C14—C15158.4 (3)
C1—C3—C4—C1752.0 (7)C13—C14—C15—C1639.1 (5)
C2—C3—C4—C1780.0 (6)C6—C7—C16—C170.8 (6)
C17—C4—C5—C60.9 (7)C8—C7—C16—C17178.3 (4)
C3—C4—C5—C6178.0 (4)C6—C7—C16—C15179.5 (4)
C4—C5—C6—C71.2 (8)C8—C7—C16—C153.0 (6)
C5—C6—C7—C161.1 (7)C14—C15—C16—C78.7 (6)
C5—C6—C7—C8178.6 (4)C14—C15—C16—C17172.7 (4)
C16—C7—C8—C9145.7 (4)C5—C4—C17—C160.7 (7)
C6—C7—C8—C936.9 (5)C3—C4—C17—C16177.7 (4)
C16—C7—C8—C1327.2 (5)C7—C16—C17—C40.7 (6)
C6—C7—C8—C13155.5 (4)C15—C16—C17—C4179.4 (4)
C16—C7—C8—C1897.2 (4)C22—N—C20—O177.4 (4)
C6—C7—C8—C1880.2 (5)C21—N—C20—O5.0 (6)
C7—C8—C9—C10171.4 (4)C22—N—C20—C121.5 (7)
C13—C8—C9—C1053.6 (5)C21—N—C20—C12179.0 (4)
C18—C8—C9—C1072.8 (4)C11—C12—C20—O102.2 (5)
C8—C9—C10—C1160.7 (6)C19—C12—C20—O136.1 (5)
C9—C10—C11—C1259.0 (6)C13—C12—C20—O13.5 (6)
C10—C11—C12—C1973.7 (5)C11—C12—C20—N73.7 (5)
C10—C11—C12—C20163.9 (4)C19—C12—C20—N48.1 (6)
C10—C11—C12—C1349.5 (5)C13—C12—C20—N170.6 (4)
C7—C8—C13—C1458.4 (4)C20—N—C22—C2389.1 (5)
C9—C8—C13—C14178.2 (4)C21—N—C22—C2393.4 (4)
C18—C8—C13—C1459.9 (4)C20—N—C22—C2797.1 (5)
C7—C8—C13—C12168.5 (4)C21—N—C22—C2780.5 (5)
C9—C8—C13—C1248.7 (5)C27—C22—C23—C241.8 (6)
C18—C8—C13—C1273.2 (5)N—C22—C23—C24175.6 (4)
C11—C12—C13—C14178.1 (4)C22—C23—C24—C250.1 (7)
C19—C12—C13—C1455.1 (5)C23—C24—C25—C261.5 (8)
C20—C12—C13—C1468.0 (4)C24—C25—C26—C271.5 (8)
C11—C12—C13—C846.4 (5)C25—C26—C27—C220.2 (7)
C19—C12—C13—C876.6 (5)C23—C22—C27—C261.8 (7)
C20—C12—C13—C8160.3 (4)N—C22—C27—C26175.7 (4)
 

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