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Volume 69 
Part 6 
Page o959  
June 2013  

Received 25 April 2013
Accepted 20 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.008 Å
R = 0.074
wR = 0.190
Data-to-parameter ratio = 17.9
Details
Open access

N,N-Dimethyldehydroabietylammonium chloride ethanol monosolvate

aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Key Laboratory of Biomass Energy and Material, Jiangsu Province, National Engineering Laboratory for Biomass Chemical Utilization, Key Laboratory on Forest Chemical Engineering, SFA, Nanjing 210042, People's Republic of China
Correspondence e-mail: rxping2001@163.com

The title compound {systematic name: 1-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]-N,N-dimethylmethanaminium chloride ethanol monosolvate}, C22H36N+·Cl-·C2H6O, was synthesized from dehydroabietylamine by N-methylation with formaldehyde/formic acid and transformation into the hydrochloride. The dehydroabietyl moiety exhibits the usual conformation with the two cyclohexane rings in chair and half-chair conformations and a trans-ring junction. The crystal structure is built up from columns of the dehydroabietyl moieties stacked along the a axis. These columns are held together by the chloride ions via N-H...Cl and C-H...Cl interactions, which establish a two-dimensional network parallel to (010). The ethanol solvent molecules are located between the columns and anchored via O-H...Cl hydrogen bonds.

Related literature

For the biological activity of dehydroabietylamine derivatives, see: Goodson et al. (1999[Goodson, B., Ehrhardt, A., Simon, N. G., Nuss, J., Johnson, K., Giedlin, M., Yamamoto, R., Moos, W. H. & Krebber, A. (1999). Antimicrob. Agents Chemother. 43, 1429-1434.]); Rao et al. (2008[Rao, X. P., Song, Z. Q. & He, L. (2008). Heteroat. Chem. 19, 512-515.]); Wilkerson et al. (1993[Wilkerson, W. W., Galbraith, W., Delucca, I. & Harris, R. R. (1993). Bioorg. Med. Chem. Lett. 3, 2087-2092.]); For the crystal structures of dehydroabietic acid derivatives, see Rao et al. (2006[Rao, X.-P., Song, Z.-Q., Gong, Y., Yao, X.-J. & Shang, S.-B. (2006). Acta Cryst. E62, o3450-o3451.], 2009[Rao, X.-P., Song, Z.-Q. & Shang, S.-B. (2009). Acta Cryst. E65, o2402.]).

[Scheme 1]

Experimental

Crystal data
  • C22H36N+·Cl-·C2H6O

  • Mr = 396.04

  • Monoclinic, P 21

  • a = 6.0560 (12) Å

  • b = 10.963 (2) Å

  • c = 18.554 (4) Å

  • [beta] = 98.62 (3)°

  • V = 1217.9 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.951, Tmax = 0.983

  • 4924 measured reflections

  • 4476 independent reflections

  • 2605 reflections with I > 2[sigma](I)

  • Rint = 0.026

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.190

  • S = 0.99

  • 4476 reflections

  • 250 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2102 Friedel pairs

  • Flack parameter: -0.02 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N-H0B...Cl 0.91 2.27 3.097 (4) 152
O-H0A...Cl 0.82 2.27 3.092 (9) 178
C18-H18B...Cli 0.96 2.78 3.694 (6) 160
C18-H18C...Clii 0.96 2.84 3.693 (6) 149
C2-H2B...Cl 0.97 2.86 3.775 (5) 158
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) x+1, y, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2059 ).


Acknowledgements

This research was supported financially by grants from the National Forestry Bureau 948 (2012-4-13).

References

Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Goodson, B., Ehrhardt, A., Simon, N. G., Nuss, J., Johnson, K., Giedlin, M., Yamamoto, R., Moos, W. H. & Krebber, A. (1999). Antimicrob. Agents Chemother. 43, 1429-1434.  [ISI] [PubMed] [ChemPort]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Rao, X.-P., Song, Z.-Q., Gong, Y., Yao, X.-J. & Shang, S.-B. (2006). Acta Cryst. E62, o3450-o3451.  [CSD] [CrossRef] [ChemPort] [details]
Rao, X. P., Song, Z. Q. & He, L. (2008). Heteroat. Chem. 19, 512-515.  [ISI] [CrossRef] [ChemPort]
Rao, X.-P., Song, Z.-Q. & Shang, S.-B. (2009). Acta Cryst. E65, o2402.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wilkerson, W. W., Galbraith, W., Delucca, I. & Harris, R. R. (1993). Bioorg. Med. Chem. Lett. 3, 2087-2092.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o959  [ doi:10.1107/S1600536813013846 ]

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