organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1118

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

aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
*Correspondence e-mail: sbkf@tom.com

(Received 31 March 2009; accepted 7 April 2009; online 25 April 2009)

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[Gottstein, W. J. & Cheney, L. C. (1965). J. Org. Chem. 30, 2072-2073.]). For the biological activity of dehydro­abietylamine derivatives, see: Wilkerson et al. (1993[Wilkerson, W. W., Galbraith, W. & Delucca, I. (1993). Bioorg. Med. Chem. Lett. 3, 2087-2092.]).

[Scheme 1]

Experimental

Crystal data
  • C27H34ClN

  • Mr = 408.00

  • Triclinic, P 1

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.986

  • 6211 measured reflections

  • 4891 independent reflections

  • 3236 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) 794 Friedel pairs

  • Flack parameter: 0.19 (12)

Data collection: SMART (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of the two unique molecules of (I), showing displacement ellipsoids at the 30% probability level and the atom numbering scheme.
(E)-(4-Chlorobenzylidene){[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-1-phenanthryl]methyl}amine top
Crystal data top
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 top
Bruker APEX CCD area-detector
diffractometer
4891 independent reflections
Radiation source: fine-focus sealed tube3236 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 67
Tmin = 0.974, Tmax = 0.986k = 1012
6211 measured reflectionsl = 2022
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062 w = 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 mapAbsolute structure parameter: 0.19 (12)
Crystal data top
C27H34ClNγ = 78.224 (4)°
Mr = 408.00V = 1168.8 (4) Å3
Triclinic, P1Z = 2
a = 5.9251 (13) ÅMo Kα radiation
b = 10.783 (2) ŵ = 0.18 mm1
c = 19.163 (4) ÅT = 273 K
α = 77.402 (4)°0.15 × 0.12 × 0.08 mm
β = 85.281 (4)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
4891 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3236 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.986Rint = 0.024
6211 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.188Δρmax = 0.31 e Å3
S = 1.02Δρmin = 0.31 e Å3
4891 reflectionsAbsolute structure: Flack (1983) 794 Friedel pairs
518 parametersAbsolute structure parameter: 0.19 (12)
1347 restraints
Special details top

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) top
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)
H30.09970.73880.21230.074*
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)
H70.05500.68090.34410.069*
C80.1358 (9)0.6147 (5)0.4584 (3)0.0587 (13)
H8A0.02240.60560.45520.070*
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*
H18B0.15030.48890.65650.086*
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)
H220.02870.04300.75560.099*
C230.1107 (12)0.1300 (8)0.7793 (4)0.0816 (15)
C240.1036 (12)0.2553 (7)0.7569 (3)0.0808 (15)
H240.18330.31280.78430.097*
C250.2448 (14)0.0768 (9)0.8472 (4)0.103 (2)
H250.27940.15620.86630.124*
C260.4642 (19)0.0709 (14)0.8369 (6)0.159 (4)
H26A0.48040.01800.84570.239*
H26B0.50210.11170.78840.239*
H26C0.56640.11480.86910.239*
C270.1150 (18)0.0008 (11)0.9025 (4)0.138
H27A0.07150.08590.89460.207*
H27B0.20380.00040.94670.207*
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)
H290.98990.06970.58760.093*
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)
H320.45130.15100.45330.086*
C330.5641 (13)0.1832 (6)0.5528 (4)0.0799 (16)
H330.45820.23370.57490.096*
C340.7038 (11)0.0028 (5)0.3698 (3)0.0625 (12)
H340.57930.01040.34560.075*
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)
H490.33530.73860.04300.098*
C500.3752 (12)0.5605 (8)0.0655 (4)0.0812 (15)
C510.4841 (11)0.4363 (7)0.0415 (3)0.0777 (15)
H510.47520.37430.06760.093*
C520.2384 (14)0.6007 (9)0.1327 (4)0.0992 (19)
H520.19810.69470.13690.119*
C530.3623 (18)0.5923 (12)0.1967 (4)0.146 (3)
H53A0.26250.62990.23590.219*
H53B0.42290.50310.19770.219*
H53C0.48720.63820.20080.219*
C540.0157 (17)0.5672 (13)0.1229 (5)0.143 (3)
H54A0.03180.47480.10980.215*
H54B0.06470.59880.16670.215*
H54C0.06990.60550.08560.215*
Atomic displacement parameters (Å2) top
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)
C270.1240.1650.0860.0020.0260.019
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, º) top
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

Experimental details

Crystal data
Chemical formulaC27H34ClN
Mr408.00
Crystal system, space groupTriclinic, P1
Temperature (K)273
a, b, c (Å)5.9251 (13), 10.783 (2), 19.163 (4)
α, β, γ (°)77.402 (4), 85.281 (4), 78.224 (4)
V3)1168.8 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.15 × 0.12 × 0.08
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.974, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
6211, 4891, 3236
Rint0.024
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.188, 1.02
No. of reflections4891
No. of parameters518
No. of restraints1347
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.31
Absolute structureFlack (1983) 794 Friedel pairs
Absolute structure parameter0.19 (12)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

First citationBruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGottstein, W. J. & Cheney, L. C. (1965). J. Org. Chem. 30, 2072–2073.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWilkerson, W. W., Galbraith, W. & Delucca, I. (1993). Bioorg. Med. Chem. Lett. 3, 2087–2092.  CrossRef CAS Web of Science Google Scholar

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Volume 65| Part 5| May 2009| Page o1118
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