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Volume 69 
Part 7 
Pages o1004-o1005  
July 2013  

Received 8 May 2013
Accepted 22 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.127
Data-to-parameter ratio = 25.8
Details
Open access

(E)-1-(2-Aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
Correspondence e-mail: suchada.c@psu.ac.th

The molecule of the title heteroaryl chalcone derivative, C13H11NOS, exists in a trans-configuaration and is almost planar with a dihedral angle of 3.73 (8)° between the phenyl and thiophene rings. An intramolecular N-H...O hydrogen bond generates an S(6) ring motif. In the crystal, two adjacent molecules are linked into a dimer in an anti-parallel face-to-face manner by a pair of C-H...O interactions. Neighboring dimers are further linked into chains along the c-axis direction by N-H...N hydrogen bonds.

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Fun et al. (2011[Fun, H.-K., Suwunwong, T., Anantapong, T., Karalai, C. & Chantrapromma, S. (2011). Acta Cryst. E67, o3074-o3075.]); Suwunwong et al. (2009[Suwunwong, T., Chantrapromma, S., Pakdeevanich, P. & Fun, H.-K. (2009). Acta Cryst. E65, o1575-o1576.]). For background to and applications of chalcones, see: Go et al. (2005[Go, M.-L., Wu, X. & Liu, X.-L. (2005). Curr. Med. Chem. 12, 483-499.]); Liu et al. (2008[Liu, X. L., Xu, Y. J. & Go, M. L. (2008). Eur. J. Med. Chem. 43, 1681-1687.]); Molyneux (2004[Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.]); Nerya et al. (2004[Nerya, O., Musa, R., Khatib, S., Tamir, S. & Vaya, J. (2004). Phytochem. 65, 1389-1395.]); Ni et al. (2004[Ni, L., Meng, C. Q. & Sikorski, J. A. (2004). Expert Opin. Ther. Pat. 14, 1669-1691.]); Shenvi et al. (2013[Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.]); Suwunwong et al. (2011[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Chem. Pap. 65, 890-897.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11NOS

  • Mr = 229.30

  • Monoclinic, C 2/c

  • a = 24.9335 (4) Å

  • b = 5.0278 (1) Å

  • c = 18.6813 (3) Å

  • [beta] = 111.151 (1)°

  • V = 2184.13 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 100 K

  • 0.36 × 0.12 × 0.06 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.908, Tmax = 0.984

  • 14827 measured reflections

  • 3942 independent reflections

  • 2620 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.127

  • S = 1.04

  • 3942 reflections

  • 153 parameters

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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1 0.83 (2) 1.97 (2) 2.6253 (18) 135.6 (19)
N1-H2N1...N1i 0.86 (2) 2.34 (2) 3.184 (2) 169 (2)
C11-H11A...O1ii 0.95 2.56 3.278 (2) 133
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5065 ).


Acknowledgements

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0314/2552) is gratefully acknowledged. The authors extend their appreciation to Prince of Songkla University, the Deanship of Scientific Research at King Saud University and Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Fun, H.-K., Suwunwong, T., Anantapong, T., Karalai, C. & Chantrapromma, S. (2011). Acta Cryst. E67, o3074-o3075.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Go, M.-L., Wu, X. & Liu, X.-L. (2005). Curr. Med. Chem. 12, 483-499.  [CrossRef] [ChemPort]
Liu, X. L., Xu, Y. J. & Go, M. L. (2008). Eur. J. Med. Chem. 43, 1681-1687.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.  [ChemPort]
Nerya, O., Musa, R., Khatib, S., Tamir, S. & Vaya, J. (2004). Phytochem. 65, 1389-1395.  [CrossRef] [ChemPort]
Ni, L., Meng, C. Q. & Sikorski, J. A. (2004). Expert Opin. Ther. Pat. 14, 1669-1691.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Chem. Pap. 65, 890-897.  [CSD] [CrossRef] [ChemPort]
Suwunwong, T., Chantrapromma, S., Pakdeevanich, P. & Fun, H.-K. (2009). Acta Cryst. E65, o1575-o1576.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1004-o1005   [ doi:10.1107/S1600536813014189 ]

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