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Volume 69 
Part 10 
Page o1521  
October 2013  

Received 22 July 2013
Accepted 3 September 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.039
wR = 0.087
Data-to-parameter ratio = 14.9
Details
Open access

6-Chloro-3-[(dimethylamino)methylidene]thiochroman-4-one

aDepartment of Chemistry, Karnatak University, Dharwad 580 003, India, and bDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
Correspondence e-mail: dr_imk@yahoo.com

The asymmetric unit of the title compound, C12H12ClNOS, contains three independent molecules, with the thiochroman ring adopting a sofa conformation in each one. The crystal structure features C-H...O interactions; one of the O atoms accepts three such bonds. Together, the hydrogen bonds give rise to a molecular tape propagating in [010].

Related literature

For general background and the antifungal activity of thiochromans, see: Wang et al. (2010[Wang, G., Yang, G. L., Ma, Z. Y., Tian, W., Fang, B. L. & Li, L. B. (2010). Int. J. Chem. 1, 19-25.]); Sosnovskikh (2003[Sosnovskikh, V. Y. (2003). Russ. Chem. Rev. 72, 489-516.]). For the crystal structure of a related compound, see: Butt et al. (1988[Butt, G. L., Deady, L. W. & Mackay, M. F. (1988). J. Heterocycl. Chem. 25, 321-326.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12ClNOS

  • Mr = 253.74

  • Monoclinic, P 21

  • a = 11.0031 (3) Å

  • b = 12.5937 (3) Å

  • c = 13.0787 (3) Å

  • [beta] = 100.255 (2)°

  • V = 1783.36 (8) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 0.47 mm-1

  • T = 296 K

  • 0.18 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.920, Tmax = 0.928

  • 13306 measured reflections

  • 6540 independent reflections

  • 5418 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.087

  • S = 1.01

  • 6540 reflections

  • 440 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1a-H1a2...O1bi 0.97 2.39 3.235 (4) 144
C11a-H11d...O1bi 0.96 2.63 3.290 (4) 126
C1b-H1b2...O1a 0.97 2.43 3.284 (1) 147
C12a-H12b...O1b 0.96 2.59 3.358 (4) 137
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996)[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]; software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2641 ).


Acknowledgements

IMK is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Butt, G. L., Deady, L. W. & Mackay, M. F. (1988). J. Heterocycl. Chem. 25, 321-326.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sosnovskikh, V. Y. (2003). Russ. Chem. Rev. 72, 489-516.  [CrossRef] [ChemPort]
Wang, G., Yang, G. L., Ma, Z. Y., Tian, W., Fang, B. L. & Li, L. B. (2010). Int. J. Chem. 1, 19-25.  [ChemPort]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.


Acta Cryst (2013). E69, o1521  [ doi:10.1107/S1600536813024550 ]

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