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Volume 69 
Part 7 
Page o1169  
July 2013  

Received 6 June 2013
Accepted 25 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.045
wR = 0.102
Data-to-parameter ratio = 21.8
Details
Open access

rac-1-(5-Bromo-2-hydroxyphenyl)-1-oxopropan-2-yl morpholine-4-carbodithioate

aDepartment of Chemistry, "Al. I. Cuza" University Iasi, 11 Carol I Bvd, Iasi 700506, Romania, and bChemisches Institut der Otto-von-Guericke-Universität, Universitätsplatz 2, D-39116 Magdeburg, Germany
Correspondence e-mail: lbirsa@uaic.ro

In the racemic title compound, C14H16BrNO3S2, synthesized from the corresponding [omega]-bromopropiophenone, the dihedral angle between the plane of the phenol group and that of the planar section [maximum deviation = 0.040 (2) Å] of the morpholine-4-carbodithiolate moiety is 76.36 (10)°. A strong intramolecular phenol O-H...O hydrogen bond if present in the molecule. In the crystal, only weak C-H...S and C-H...O interactions are found.

Related literature

For the synthesis and applications of dithiocarbamates, see: Buu-Hoi & Lavit (1955[Buu-Hoi, Ng. Ph. & Lavit, D. (1955). J. Chem. Soc., pp. 18-20.]); WHO (1998[WHO (1998). http://www.inchem.org/documents/ehc/ehc/ehc78.htm .]). For applications of 1,3-dithiolium salts, see: Narita & Pittman (1976[Narita, M. & Pittman, C. U. Jr (1976). Synthesis, pp. 489-514.]); Birsa & Asaftei (2008[Birsa, M. L. & Asaftei, I. V. (2008). Monatsh. Chem. 139, 1433-1438.]). For the structure of a related morpholine-4-carbodithioate, see: Bahrin et al. (2012[Bahrin, L. G., Jones, P. G. & Hopf, H. (2012). Beilstein J. Org. Chem. 8, 1999-2003.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16BrNO3S2

  • Mr = 390.31

  • Monoclinic, P 21 /c

  • a = 11.182 (2) Å

  • b = 19.660 (4) Å

  • c = 7.4593 (15) Å

  • [beta] = 105.44 (3)°

  • V = 1580.6 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.87 mm-1

  • T = 153 K

  • 0.54 × 0.48 × 0.30 mm

Data collection
  • Stoe IPDS 2T area-detector diffractometer

  • Absorption correction: for a sphere [modification of the interpolation procedure of Dwiggins (1975[Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.])] Tmin = 0.114, Tmax = 0.140

  • 17019 measured reflections

  • 4246 independent reflections

  • 3807 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.102

  • S = 1.16

  • 4246 reflections

  • 195 parameters

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

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.78 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.76 (4) 1.86 (4) 2.558 (3) 151 (5)
C4-H4...S2i 0.95 2.79 3.712 (3) 164
C3-H3...O3ii 0.95 2.51 3.443 (4) 168
C12-H12B...O1iii 0.99 2.46 3.454 (4) 178
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z-1.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2265 ).


Acknowledgements

Part of this work was supported by a grant of the Romanian National Authority for Scientific Research, CNDI-UEFISCDI, project No. 51/2012.

References

Bahrin, L. G., Jones, P. G. & Hopf, H. (2012). Beilstein J. Org. Chem. 8, 1999-2003.  [CrossRef] [ChemPort] [PubMed]
Birsa, M. L. & Asaftei, I. V. (2008). Monatsh. Chem. 139, 1433-1438.  [CrossRef] [ChemPort]
Buu-Hoi, Ng. Ph. & Lavit, D. (1955). J. Chem. Soc., pp. 18-20.
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.  [CrossRef] [IUCr Journals]
Narita, M. & Pittman, C. U. Jr (1976). Synthesis, pp. 489-514.  [CrossRef] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.
WHO (1998). http://www.inchem.org/documents/ehc/ehc/ehc78.htm .


Acta Cryst (2013). E69, o1169  [ doi:10.1107/S1600536813017509 ]

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