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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1118.
Published online 2009 April 25. doi:  10.1107/S1600536809013245
PMCID: PMC2977794

(E)-(4-Chloro­benzyl­idene){[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa­hydro-1-phenanthryl]­methyl}amine

Abstract

The title compound, C27H34ClN, has been synthesized from 4-chloro­benzaldehyde and dehydro­abietylamine. There are two unique mol­ecules in the unit cell. Each mol­ecule has three chiral centres, which exhibit R, S and R absolute configurations. The two cyclo­hexane rings form a trans ring junction with classical chair and half-chair conformations.

Related literature

For the background to dehydro­abietylamine, an important chiral diterpenic amine with a hydro­phanthrene structure, see: Gottstein & Cheney (1965 [triangle]). For the biological activity of dehydro­abietylamine derivatives, see: Wilkerson et al. (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1118-scheme1.jpg

Experimental

Crystal data

  • C27H34ClN
  • M r = 408.00
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1118-efi1.jpg
  • a = 5.9251 (13) Å
  • b = 10.783 (2) Å
  • c = 19.163 (4) Å
  • α = 77.402 (4)°
  • β = 85.281 (4)°
  • γ = 78.224 (4)°
  • V = 1168.8 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 273 K
  • 0.15 × 0.12 × 0.08 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.974, T max = 0.986
  • 6211 measured reflections
  • 4891 independent reflections
  • 3236 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.188
  • S = 1.02
  • 4891 reflections
  • 518 parameters
  • 1347 restraints
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.31 e Å−3
  • Absolute structure: Flack (1983 [triangle]) 794 Friedel pairs
  • Flack parameter: 0.19 (12)

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013245/at2759sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013245/at2759Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Fund of Jiangsu Province under grant No. BK2006011.

supplementary crystallographic information

Comment

Dehydroabietylamine is an important chiral diterpenic amine with the hydrophanthrene structure (Gottstein et al., 1965). Dehydroabietylamine derivatives exhibit a wide range of biological activity (Wilkerson et al., 1993). Although much attention has been paid to the bioactivity of dehydroabietylamine derivatives, the crystal structure of the title compound has not yet been reported and we describe its structure here, Fig 1. The compound crystallises with two unique molecules in the triclinic unit cell. Each molecule contains four rings. The two cyclohexane rings with a classical chair and half-chair conformations form a trans ring junction. The two methyl groups attached to the cyclohexane rings are in axial positions. The carbon atoms C11 and C18 in the cyclohexane ring and the atoms in the conjoint benzene ring are in the same plane.

Experimental

A mixture of 4 - chlorobenzaldehyde (0.03 mol), dehydroabietylamine (0.03 mol) and ethanol (150 ml) was refluxed for 4 h. The resulting mixture was cooled to room temperature, then filtered. The precipitate was washed with water and ethanol. Upon recrystallization from ethanol, colorless crystals of the title compound were obtained.

Refinement

All H atoms bonded to the C atoms were placed geometrically at the distances of 0.93–0.98 Å and included in the refinement in the riding approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.

Figures

Fig. 1.
A view of the two unique molecules of (I), showing displacement ellipsoids at the 30% probability level and the atom numbering scheme.

Crystal data

C27H34ClNZ = 2
Mr = 408.00F(000) = 440
Triclinic, P1Dx = 1.159 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9251 (13) ÅCell parameters from 1191 reflections
b = 10.783 (2) Åθ = 2.4–18.6°
c = 19.163 (4) ŵ = 0.18 mm1
α = 77.402 (4)°T = 273 K
β = 85.281 (4)°Block, colourless
γ = 78.224 (4)°0.15 × 0.12 × 0.08 mm
V = 1168.8 (4) Å3

Data collection

Bruker APEX CCD area-detector diffractometer4891 independent reflections
Radiation source: fine-focus sealed tube3236 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→7
Tmin = 0.974, Tmax = 0.986k = −10→12
6211 measured reflectionsl = −20→22

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062w = 1/[σ2(Fo2) + (0.1124P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.188(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.31 e Å3
4891 reflectionsΔρmin = −0.31 e Å3
518 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1347 restraintsExtinction coefficient: 0.012 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983) 794 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.19 (12)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
Cl10.3555 (3)0.97493 (17)0.04545 (10)0.0952 (6)
Cl20.7197 (5)−0.2151 (2)0.68356 (11)0.1210 (9)
N10.2137 (8)0.6837 (4)0.3893 (3)0.0618 (12)
N20.8562 (8)0.0563 (4)0.3353 (3)0.0641 (13)
C10.2792 (10)0.8976 (6)0.1296 (3)0.0635 (14)
C20.0903 (11)0.8392 (6)0.1394 (3)0.0670 (14)
H20.00420.84140.10050.080*
C30.0289 (10)0.7777 (5)0.2063 (3)0.0615 (13)
H3−0.09970.73880.21230.074*
C40.1535 (9)0.7718 (5)0.2660 (3)0.0564 (12)
C50.3454 (10)0.8302 (5)0.2544 (3)0.0613 (13)
H50.43650.82520.29250.074*
C60.4031 (11)0.8957 (6)0.1868 (4)0.0690 (14)
H60.52680.93860.18050.083*
C70.0872 (10)0.7066 (5)0.3372 (3)0.0578 (12)
H7−0.05500.68090.34410.069*
C80.1358 (9)0.6147 (5)0.4584 (3)0.0587 (13)
H8A−0.02240.60560.45520.070*
H8B0.13750.66600.49410.070*
C90.2843 (9)0.4798 (5)0.4834 (3)0.0548 (12)
C100.1857 (9)0.4181 (5)0.5573 (3)0.0504 (11)
H100.02200.42390.54970.061*
C110.2793 (9)0.2695 (5)0.5851 (3)0.0534 (11)
C120.2433 (10)0.2005 (6)0.5256 (3)0.0614 (12)
H12A0.31020.10920.53950.074*
H12B0.07910.20790.52080.074*
C130.3507 (10)0.2556 (6)0.4531 (3)0.0638 (13)
H13A0.51680.24150.45650.077*
H13B0.31820.21050.41760.077*
C140.2572 (10)0.3985 (5)0.4296 (3)0.0584 (12)
H14A0.09460.41060.42070.070*
H14B0.33520.43040.38480.070*
C150.5355 (9)0.4965 (6)0.4838 (3)0.0677 (15)
H15A0.57210.55400.44050.102*
H15B0.63660.41380.48700.102*
H15C0.55470.53200.52420.102*
C160.5323 (10)0.2337 (7)0.6044 (4)0.0767 (17)
H16A0.56710.14460.62850.115*
H16B0.56080.28750.63530.115*
H16C0.62820.24660.56160.115*
C170.1851 (11)0.4910 (6)0.6172 (3)0.0666 (13)
H17A0.14790.58360.59880.080*
H17B0.33580.47010.63780.080*
C180.0017 (11)0.4489 (6)0.6743 (3)0.0716 (14)
H18A0.01820.48050.71690.086*
H18B−0.15030.48890.65650.086*
C190.0174 (10)0.3059 (6)0.6941 (3)0.0651 (13)
C200.1373 (9)0.2239 (6)0.6528 (3)0.0591 (12)
C210.1391 (11)0.0909 (6)0.6766 (3)0.0714 (14)
H210.22060.03250.65000.086*
C220.0201 (12)0.0457 (7)0.7397 (4)0.0825 (16)
H220.0287−0.04300.75560.099*
C23−0.1107 (12)0.1300 (8)0.7793 (4)0.0816 (15)
C24−0.1036 (12)0.2553 (7)0.7569 (3)0.0808 (15)
H24−0.18330.31280.78430.097*
C25−0.2448 (14)0.0768 (9)0.8472 (4)0.103 (2)
H25−0.27940.15620.86630.124*
C26−0.4642 (19)0.0709 (14)0.8369 (6)0.159 (4)
H26A−0.4804−0.01800.84570.239*
H26B−0.50210.11170.78840.239*
H26C−0.56640.11480.86910.239*
C27−0.1150 (18)0.0008 (11)0.9025 (4)0.138
H27A−0.0715−0.08590.89460.207*
H27B−0.20380.00040.94670.207*
H27C0.02120.03490.90480.207*
C280.7244 (12)−0.1573 (6)0.5922 (4)0.0716 (15)
C290.8802 (12)−0.0856 (6)0.5604 (4)0.0777 (15)
H290.9899−0.06970.58760.093*
C300.8785 (11)−0.0359 (6)0.4880 (3)0.0708 (15)
H300.98630.01390.46680.085*
C310.7175 (11)−0.0593 (6)0.4465 (3)0.0634 (13)
C320.5608 (12)−0.1338 (6)0.4801 (4)0.0719 (14)
H320.4513−0.15100.45330.086*
C330.5641 (13)−0.1832 (6)0.5528 (4)0.0799 (16)
H330.4582−0.23370.57490.096*
C340.7038 (11)−0.0028 (5)0.3698 (3)0.0625 (12)
H340.5793−0.01040.34560.075*
C350.8203 (10)0.1093 (5)0.2595 (3)0.0603 (13)
H35A0.66160.11130.24960.072*
H35B0.91920.05300.23170.072*
C360.8725 (9)0.2479 (5)0.2359 (3)0.0526 (11)
C370.7780 (9)0.3039 (5)0.1601 (3)0.0538 (11)
H370.61780.29140.16520.065*
C380.7591 (9)0.4506 (5)0.1303 (3)0.0527 (11)
C390.6276 (10)0.5216 (5)0.1872 (3)0.0548 (12)
H39A0.62860.61340.17190.066*
H39B0.46820.51080.19060.066*
C400.7289 (10)0.4734 (5)0.2607 (3)0.0585 (13)
H40A0.88390.49090.25840.070*
H40B0.63650.52040.29430.070*
C410.7370 (9)0.3309 (5)0.2873 (3)0.0522 (11)
H41A0.58050.31510.29420.063*
H41B0.80780.30410.33350.063*
C421.1337 (9)0.2383 (6)0.2398 (3)0.0732 (17)
H42A1.21250.20280.20070.110*
H42B1.18590.18320.28430.110*
H42C1.16590.32310.23700.110*
C430.9946 (10)0.4930 (7)0.1118 (3)0.0677 (15)
H43A0.97080.58070.08520.102*
H43B1.08920.43740.08350.102*
H43C1.07000.48730.15510.102*
C440.6259 (9)0.4867 (5)0.0612 (3)0.0558 (11)
C450.6104 (11)0.3978 (6)0.0217 (3)0.0655 (12)
C460.7238 (13)0.2559 (7)0.0427 (3)0.0797 (15)
H46A0.60460.20470.05720.096*
H46B0.80740.22870.00130.096*
C470.8876 (12)0.2288 (6)0.1026 (3)0.0698 (14)
H47A1.03180.25520.08440.084*
H47B0.92000.13680.12320.084*
C480.5188 (11)0.6147 (6)0.0351 (3)0.0697 (13)
H480.52860.67720.06080.084*
C490.3999 (12)0.6518 (8)−0.0268 (3)0.0820 (16)
H490.33530.7386−0.04300.098*
C500.3752 (12)0.5605 (8)−0.0655 (4)0.0812 (15)
C510.4841 (11)0.4363 (7)−0.0415 (3)0.0777 (15)
H510.47520.3743−0.06760.093*
C520.2384 (14)0.6007 (9)−0.1327 (4)0.0992 (19)
H520.19810.6947−0.13690.119*
C530.3623 (18)0.5923 (12)−0.1967 (4)0.146 (3)
H53A0.26250.6299−0.23590.219*
H53B0.42290.5031−0.19770.219*
H53C0.48720.6382−0.20080.219*
C540.0157 (17)0.5672 (13)−0.1229 (5)0.143 (3)
H54A0.03180.4748−0.10980.215*
H54B−0.06470.5988−0.16670.215*
H54C−0.06990.6055−0.08560.215*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1210 (15)0.0791 (12)0.0781 (11)−0.0183 (11)0.0226 (10)−0.0107 (9)
Cl20.186 (2)0.0886 (14)0.0764 (12)−0.0194 (15)0.0093 (13)−0.0028 (11)
N10.057 (3)0.054 (3)0.073 (3)−0.010 (2)0.001 (3)−0.012 (2)
N20.065 (3)0.049 (3)0.072 (3)0.000 (2)−0.005 (3)−0.006 (2)
C10.067 (3)0.051 (3)0.071 (3)−0.005 (2)0.004 (3)−0.015 (2)
C20.067 (3)0.056 (3)0.077 (3)−0.007 (2)−0.011 (3)−0.016 (3)
C30.061 (3)0.050 (3)0.075 (3)−0.010 (2)−0.008 (2)−0.016 (2)
C40.055 (3)0.042 (2)0.072 (3)−0.006 (2)−0.003 (2)−0.016 (2)
C50.056 (3)0.053 (3)0.074 (3)−0.005 (2)−0.009 (2)−0.014 (2)
C60.062 (3)0.059 (3)0.086 (3)−0.015 (2)−0.002 (3)−0.014 (3)
C70.048 (2)0.049 (2)0.074 (3)−0.005 (2)−0.006 (2)−0.011 (2)
C80.054 (3)0.049 (3)0.071 (3)−0.007 (2)−0.001 (2)−0.012 (2)
C90.041 (2)0.057 (2)0.065 (3)−0.005 (2)−0.002 (2)−0.013 (2)
C100.045 (2)0.050 (2)0.059 (2)−0.0099 (19)−0.002 (2)−0.016 (2)
C110.045 (2)0.055 (2)0.057 (2)−0.0049 (19)−0.002 (2)−0.009 (2)
C120.059 (3)0.058 (3)0.065 (3)−0.004 (2)0.000 (2)−0.016 (2)
C130.062 (3)0.058 (3)0.068 (3)−0.001 (2)0.002 (2)−0.018 (2)
C140.050 (2)0.058 (3)0.063 (3)−0.003 (2)0.007 (2)−0.015 (2)
C150.045 (3)0.073 (3)0.084 (3)−0.017 (3)−0.005 (3)−0.007 (3)
C160.056 (3)0.079 (4)0.084 (4)−0.003 (3)−0.008 (3)−0.001 (3)
C170.071 (3)0.064 (3)0.068 (3)−0.012 (2)−0.006 (2)−0.019 (2)
C180.074 (3)0.075 (3)0.064 (3)−0.008 (2)0.005 (2)−0.020 (2)
C190.062 (3)0.069 (3)0.062 (2)−0.010 (2)−0.001 (2)−0.013 (2)
C200.054 (2)0.061 (2)0.061 (2)−0.011 (2)−0.006 (2)−0.009 (2)
C210.069 (3)0.073 (3)0.068 (3)−0.006 (2)−0.005 (2)−0.010 (2)
C220.079 (3)0.084 (3)0.076 (3)−0.019 (3)0.000 (3)0.004 (3)
C230.070 (3)0.096 (3)0.068 (3)−0.009 (3)0.003 (3)−0.003 (3)
C240.075 (3)0.094 (3)0.067 (3)−0.011 (3)0.002 (3)−0.012 (3)
C250.079 (4)0.128 (4)0.086 (4)−0.014 (4)0.003 (3)0.006 (4)
C260.122 (6)0.211 (8)0.125 (6)−0.046 (6)0.007 (5)0.017 (6)
C270.1240.1650.086−0.0020.0260.019
C280.084 (3)0.049 (3)0.078 (3)−0.008 (3)−0.001 (3)−0.011 (3)
C290.086 (3)0.066 (3)0.083 (3)−0.017 (3)−0.010 (3)−0.014 (3)
C300.075 (3)0.061 (3)0.078 (3)−0.020 (3)−0.004 (3)−0.011 (3)
C310.068 (3)0.051 (2)0.072 (3)−0.015 (2)0.001 (2)−0.015 (2)
C320.075 (3)0.060 (3)0.082 (3)−0.019 (3)−0.001 (3)−0.013 (3)
C330.085 (3)0.062 (3)0.088 (3)−0.013 (3)0.011 (3)−0.011 (3)
C340.063 (2)0.051 (2)0.074 (3)−0.007 (2)−0.003 (2)−0.016 (2)
C350.060 (3)0.053 (3)0.064 (3)0.000 (2)−0.005 (2)−0.012 (2)
C360.046 (2)0.051 (2)0.060 (2)−0.005 (2)−0.001 (2)−0.015 (2)
C370.050 (2)0.055 (2)0.058 (2)−0.0077 (19)0.000 (2)−0.019 (2)
C380.048 (2)0.056 (2)0.056 (2)−0.012 (2)0.003 (2)−0.015 (2)
C390.055 (2)0.051 (2)0.059 (2)−0.007 (2)0.002 (2)−0.019 (2)
C400.059 (3)0.060 (3)0.061 (3)−0.009 (2)0.003 (2)−0.024 (2)
C410.051 (2)0.052 (2)0.056 (2)−0.014 (2)0.000 (2)−0.014 (2)
C420.045 (3)0.082 (4)0.082 (4)−0.001 (3)−0.001 (3)−0.005 (3)
C430.057 (3)0.078 (3)0.065 (3)−0.018 (3)0.001 (3)−0.006 (3)
C440.052 (2)0.061 (2)0.055 (2)−0.013 (2)−0.001 (2)−0.013 (2)
C450.068 (3)0.069 (3)0.058 (2)−0.010 (2)−0.002 (2)−0.016 (2)
C460.092 (3)0.077 (3)0.069 (3)−0.005 (3)−0.007 (3)−0.021 (2)
C470.075 (3)0.062 (3)0.068 (3)0.005 (2)−0.002 (2)−0.022 (2)
C480.068 (3)0.074 (3)0.063 (2)−0.006 (2)−0.002 (2)−0.013 (2)
C490.074 (3)0.089 (3)0.070 (3)0.002 (3)−0.004 (3)−0.005 (3)
C500.070 (3)0.102 (3)0.065 (3)−0.009 (3)−0.009 (3)−0.009 (3)
C510.080 (3)0.095 (3)0.061 (3)−0.021 (3)−0.007 (3)−0.018 (3)
C520.089 (4)0.128 (4)0.073 (3)−0.007 (3)−0.011 (3)−0.015 (3)
C530.131 (6)0.207 (8)0.081 (5)−0.020 (6)−0.009 (5)0.003 (6)
C540.108 (6)0.211 (8)0.098 (5)−0.015 (6)−0.018 (5)−0.013 (6)

Geometric parameters (Å, °)

Cl1—C11.717 (6)C27—H27A0.9600
Cl2—C281.726 (7)C27—H27B0.9600
N1—C71.250 (7)C27—H27C0.9600
N1—C81.460 (7)C28—C291.347 (9)
N2—C341.269 (7)C28—C331.366 (10)
N2—C351.455 (7)C29—C301.373 (9)
C1—C61.364 (8)C29—H290.9300
C1—C21.373 (8)C30—C311.385 (9)
C2—C31.367 (8)C30—H300.9300
C2—H20.9300C31—C321.380 (8)
C3—C41.394 (8)C31—C341.465 (8)
C3—H30.9300C32—C331.380 (9)
C4—C51.389 (8)C32—H320.9300
C4—C71.454 (7)C33—H330.9300
C5—C61.385 (8)C34—H340.9300
C5—H50.9300C35—C361.551 (8)
C6—H60.9300C35—H35A0.9700
C7—H70.9300C35—H35B0.9700
C8—C91.538 (8)C36—C421.537 (8)
C8—H8A0.9700C36—C411.543 (8)
C8—H8B0.9700C36—C371.549 (7)
C9—C141.528 (8)C37—C471.531 (8)
C9—C151.536 (7)C37—C381.545 (7)
C9—C101.550 (7)C37—H370.9800
C10—C171.526 (8)C38—C441.532 (7)
C10—C111.572 (7)C38—C391.536 (7)
C10—H100.9800C38—C431.546 (7)
C11—C161.525 (8)C39—C401.520 (7)
C11—C201.532 (8)C39—H39A0.9700
C11—C121.541 (8)C39—H39B0.9700
C12—C131.528 (8)C40—C411.502 (8)
C12—H12A0.9700C40—H40A0.9700
C12—H12B0.9700C40—H40B0.9700
C13—C141.508 (8)C41—H41A0.9700
C13—H13A0.9700C41—H41B0.9700
C13—H13B0.9700C42—H42A0.9600
C14—H14A0.9700C42—H42B0.9600
C14—H14B0.9700C42—H42C0.9600
C15—H15A0.9600C43—H43A0.9600
C15—H15B0.9600C43—H43B0.9600
C15—H15C0.9600C43—H43C0.9600
C16—H16A0.9600C44—C451.366 (9)
C16—H16B0.9600C44—C481.396 (8)
C16—H16C0.9600C45—C511.416 (8)
C17—C181.540 (9)C45—C461.520 (9)
C17—H17A0.9700C46—C471.505 (9)
C17—H17B0.9700C46—H46A0.9700
C18—C191.490 (9)C46—H46B0.9700
C18—H18A0.9700C47—H47A0.9700
C18—H18B0.9700C47—H47B0.9700
C19—C201.368 (9)C48—C491.371 (9)
C19—C241.411 (8)C48—H480.9300
C20—C211.405 (8)C49—C501.391 (10)
C21—C221.392 (8)C49—H490.9300
C21—H210.9300C50—C511.360 (10)
C22—C231.385 (10)C50—C521.512 (10)
C22—H220.9300C51—H510.9300
C23—C241.334 (10)C52—C531.388 (11)
C23—C251.532 (10)C52—C541.425 (12)
C24—H240.9300C52—H520.9800
C25—C261.347 (12)C53—H53A0.9600
C25—C271.372 (11)C53—H53B0.9600
C25—H250.9800C53—H53C0.9600
C26—H26A0.9600C54—H54A0.9600
C26—H26B0.9600C54—H54B0.9600
C26—H26C0.9600C54—H54C0.9600
C7—N1—C8118.9 (5)H27B—C27—H27C109.5
C34—N2—C35116.7 (5)C29—C28—C33120.5 (6)
C6—C1—C2119.9 (6)C29—C28—Cl2120.6 (6)
C6—C1—Cl1120.2 (5)C33—C28—Cl2118.8 (5)
C2—C1—Cl1119.8 (5)C28—C29—C30120.5 (7)
C3—C2—C1119.9 (6)C28—C29—H29119.7
C3—C2—H2120.0C30—C29—H29119.7
C1—C2—H2120.0C29—C30—C31120.6 (6)
C2—C3—C4121.9 (5)C29—C30—H30119.7
C2—C3—H3119.1C31—C30—H30119.7
C4—C3—H3119.1C32—C31—C30117.9 (6)
C5—C4—C3117.0 (5)C32—C31—C34120.0 (6)
C5—C4—C7121.4 (5)C30—C31—C34122.0 (5)
C3—C4—C7121.7 (5)C33—C32—C31121.0 (7)
C6—C5—C4121.0 (6)C33—C32—H32119.5
C6—C5—H5119.5C31—C32—H32119.5
C4—C5—H5119.5C28—C33—C32119.4 (6)
C1—C6—C5120.2 (6)C28—C33—H33120.3
C1—C6—H6119.9C32—C33—H33120.3
C5—C6—H6119.9N2—C34—C31122.2 (6)
N1—C7—C4122.6 (5)N2—C34—H34118.9
N1—C7—H7118.7C31—C34—H34118.9
C4—C7—H7118.7N2—C35—C36112.4 (5)
N1—C8—C9113.4 (4)N2—C35—H35A109.1
N1—C8—H8A108.9C36—C35—H35A109.1
C9—C8—H8A108.9N2—C35—H35B109.1
N1—C8—H8B108.9C36—C35—H35B109.1
C9—C8—H8B108.9H35A—C35—H35B107.9
H8A—C8—H8B107.7C42—C36—C41110.9 (5)
C14—C9—C15111.1 (5)C42—C36—C37114.4 (4)
C14—C9—C8107.0 (4)C41—C36—C37108.2 (4)
C15—C9—C8107.7 (5)C42—C36—C35108.0 (5)
C14—C9—C10108.4 (4)C41—C36—C35108.1 (4)
C15—C9—C10114.2 (4)C37—C36—C35107.1 (4)
C8—C9—C10108.2 (4)C47—C37—C38109.7 (4)
C17—C10—C9115.9 (4)C47—C37—C36115.0 (4)
C17—C10—C11109.9 (4)C38—C37—C36117.8 (4)
C9—C10—C11116.3 (4)C47—C37—H37104.2
C17—C10—H10104.4C38—C37—H37104.2
C9—C10—H10104.4C36—C37—H37104.2
C11—C10—H10104.4C44—C38—C39110.6 (4)
C16—C11—C20107.2 (4)C44—C38—C37108.2 (4)
C16—C11—C12109.3 (5)C39—C38—C37107.5 (4)
C20—C11—C12110.2 (4)C44—C38—C43107.4 (4)
C16—C11—C10115.2 (5)C39—C38—C43109.2 (5)
C20—C11—C10108.0 (4)C37—C38—C43113.9 (5)
C12—C11—C10106.9 (4)C40—C39—C38113.3 (4)
C13—C12—C11113.1 (5)C40—C39—H39A108.9
C13—C12—H12A109.0C38—C39—H39A108.9
C11—C12—H12A109.0C40—C39—H39B108.9
C13—C12—H12B109.0C38—C39—H39B108.9
C11—C12—H12B109.0H39A—C39—H39B107.7
H12A—C12—H12B107.8C41—C40—C39111.9 (5)
C14—C13—C12111.3 (5)C41—C40—H40A109.2
C14—C13—H13A109.4C39—C40—H40A109.2
C12—C13—H13A109.4C41—C40—H40B109.2
C14—C13—H13B109.4C39—C40—H40B109.2
C12—C13—H13B109.4H40A—C40—H40B107.9
H13A—C13—H13B108.0C40—C41—C36113.1 (4)
C13—C14—C9114.5 (5)C40—C41—H41A109.0
C13—C14—H14A108.6C36—C41—H41A108.9
C9—C14—H14A108.6C40—C41—H41B108.9
C13—C14—H14B108.6C36—C41—H41B109.0
C9—C14—H14B108.6H41A—C41—H41B107.8
H14A—C14—H14B107.6C36—C42—H42A109.5
C9—C15—H15A109.5C36—C42—H42B109.5
C9—C15—H15B109.5H42A—C42—H42B109.5
H15A—C15—H15B109.5C36—C42—H42C109.5
C9—C15—H15C109.5H42A—C42—H42C109.5
H15A—C15—H15C109.5H42B—C42—H42C109.5
H15B—C15—H15C109.5C38—C43—H43A109.5
C11—C16—H16A109.5C38—C43—H43B109.5
C11—C16—H16B109.5H43A—C43—H43B109.5
H16A—C16—H16B109.5C38—C43—H43C109.5
C11—C16—H16C109.5H43A—C43—H43C109.5
H16A—C16—H16C109.5H43B—C43—H43C109.5
H16B—C16—H16C109.5C45—C44—C48117.1 (5)
C10—C17—C18107.3 (5)C45—C44—C38122.4 (5)
C10—C17—H17A110.3C48—C44—C38120.5 (5)
C18—C17—H17A110.3C44—C45—C51120.0 (6)
C10—C17—H17B110.3C44—C45—C46122.7 (5)
C18—C17—H17B110.3C51—C45—C46117.3 (6)
H17A—C17—H17B108.5C47—C46—C45113.3 (6)
C19—C18—C17113.5 (5)C47—C46—H46A108.9
C19—C18—H18A108.9C45—C46—H46A108.9
C17—C18—H18A108.9C47—C46—H46B108.9
C19—C18—H18B108.9C45—C46—H46B108.9
C17—C18—H18B108.9H46A—C46—H46B107.7
H18A—C18—H18B107.7C46—C47—C37109.1 (5)
C20—C19—C24119.5 (6)C46—C47—H47A109.9
C20—C19—C18122.6 (5)C37—C47—H47A109.9
C24—C19—C18117.9 (6)C46—C47—H47B109.9
C19—C20—C21117.6 (5)C37—C47—H47B109.9
C19—C20—C11123.1 (5)H47A—C47—H47B108.3
C21—C20—C11119.2 (5)C49—C48—C44122.6 (7)
C22—C21—C20120.7 (6)C49—C48—H48118.7
C22—C21—H21119.7C44—C48—H48118.7
C20—C21—H21119.7C48—C49—C50120.4 (7)
C23—C22—C21121.4 (7)C48—C49—H49119.8
C23—C22—H22119.3C50—C49—H49119.8
C21—C22—H22119.3C51—C50—C49117.3 (6)
C24—C23—C22116.8 (6)C51—C50—C52122.2 (7)
C24—C23—C25123.3 (8)C49—C50—C52120.5 (7)
C22—C23—C25119.8 (7)C50—C51—C45122.4 (7)
C23—C24—C19124.0 (7)C50—C51—H51118.8
C23—C24—H24118.0C45—C51—H51118.8
C19—C24—H24118.0C53—C52—C54119.0 (9)
C26—C25—C27124.8 (8)C53—C52—C50116.6 (7)
C26—C25—C23114.4 (7)C54—C52—C50113.6 (7)
C27—C25—C23116.2 (7)C53—C52—H52101.1
C26—C25—H2597.1C54—C52—H52101.1
C27—C25—H2597.1C50—C52—H52101.1
C23—C25—H2597.1C52—C53—H53A109.5
C25—C26—H26A109.5C52—C53—H53B109.5
C25—C26—H26B109.5H53A—C53—H53B109.5
H26A—C26—H26B109.5C52—C53—H53C109.5
C25—C26—H26C109.5H53A—C53—H53C109.5
H26A—C26—H26C109.5H53B—C53—H53C109.5
H26B—C26—H26C109.5C52—C54—H54A109.5
C25—C27—H27A109.5C52—C54—H54B109.5
C25—C27—H27B109.5H54A—C54—H54B109.5
H27A—C27—H27B109.5C52—C54—H54C109.5
C25—C27—H27C109.5H54A—C54—H54C109.5
H27A—C27—H27C109.5H54B—C54—H54C109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2759).

References

  • Bruker (1997). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gottstein, W. J. & Cheney, L. C. (1965). J. Org. Chem.30, 2072–2073.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wilkerson, W. W., Galbraith, W. & Delucca, I. (1993). Bioorg. Med. Chem. Lett.3, 2087–2092.

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