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Volume 67 
Part 8 
Page o1883  
August 2011  

Received 23 June 2011
Accepted 27 June 2011
Online 2 July 2011

Key indicators
Single-crystal X-ray study
T = 170 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.043
wR = 0.116
Data-to-parameter ratio = 15.3
Details
Open access

9-[3-(Dimethylamino)propyl]-2-trifluoromethyl-9H-thioxanthen-9-ol

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Chemistry, Sambhram Institute of Technology, Bangalore 560 097, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C19H20F3NOS, the dihedral angle between the mean planes of the two benzene rings attached to the thioxanthene ring is 41.8 (7)°; the latter has a slightly distorted boat conformation. The F atoms are disordered over three sets of sites [occupancy ratio = 0.564 (10):0.287 (10):0.148 (5)] and the methyl groups are disordered over two sets of sites [occupancy ratio = 0.72 (4):0.28 (4)]. The crystal packing is stabilized by O-H...N and C-H...S hydrogen bonds and weak C-H...Cg interactions.

Related literature

For photo-initiators with excellent capabilities in UV-curing materials, see: Fouassier et al. (1995[Fouassier, J. P., Ruhlmann, D., Graff, D., Morlet-Savary, F. & Wieder, F. (1995). Prog. Org. Coat. 25, 235-271.]); Roffey (1997[Roffey, C. (1997). In Photogeneration of Reactive Species for UV-Curing. Sussex, England: Wiley.]). For related structures, see: Post et al. (1975a[Post, M. L., Kennard, O. & Horn, A. S. (1975a). Acta Cryst. B31, 2724-2726.],b[Post, M. L., Kennard, O., Sheldrick, G. M. & Horn, A. S. (1975b). Acta Cryst. B31, 2366-2368.]); Liu, (2009[Liu, G. (2009). Acta Cryst. E65, o613.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20F3NOS

  • Mr = 367.42

  • Monoclinic, P 21 /n

  • a = 7.6183 (3) Å

  • b = 13.9605 (4) Å

  • c = 17.4172 (7) Å

  • [beta] = 101.053 (4)°

  • V = 1818.05 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 170 K

  • 0.35 × 0.33 × 0.30 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.929, Tmax = 0.939

  • 17330 measured reflections

  • 4697 independent reflections

  • 3901 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.116

  • S = 1.05

  • 4697 reflections

  • 306 parameters

  • 238 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2-C7 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1 0.87 (2) 1.84 (2) 2.7141 (17) 176 (2)
C15-H15A...S1 0.99 2.76 3.4165 (15) 124
C5-H5A...Cg3i 0.95 2.96 3.798 (3) 148
C17-H17A...Cg2ii 0.99 2.97 3.949 (3) 170
C17-H17B...Cg3ii 0.99 2.83 3.659 (3) 142
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: TK2761 ).


Acknowledgements

MSS thanks the University of Mysore and R. L. Fine Chem, Bangalore, for access to their research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Fouassier, J. P., Ruhlmann, D., Graff, D., Morlet-Savary, F. & Wieder, F. (1995). Prog. Org. Coat. 25, 235-271.  [CrossRef] [ChemPort] [ISI]
Liu, G. (2009). Acta Cryst. E65, o613.  [CSD] [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Post, M. L., Kennard, O. & Horn, A. S. (1975a). Acta Cryst. B31, 2724-2726.  [CrossRef] [details] [ISI]
Post, M. L., Kennard, O., Sheldrick, G. M. & Horn, A. S. (1975b). Acta Cryst. B31, 2366-2368.  [CrossRef] [details] [ISI]
Roffey, C. (1997). In Photogeneration of Reactive Species for UV-Curing. Sussex, England: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2011). E67, o1883  [ doi:10.1107/S1600536811025311 ]

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