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Volume 69 
Part 6 
Pages o906-o907  
June 2013  

Received 21 April 2013
Accepted 10 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.155
Data-to-parameter ratio = 13.5
Details
Open access
ADDENDA AND ERRATA

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1-[4-(Dimethylamino)benzylidene]-4-o-tolylthiosemicarbazide

aDepartment of Chemistry, Xiamen University, Xiamen 361005, People's Republic of China
Correspondence e-mail: linlr@xmu.edu.cn

The asymmetric unit of the title compound, C17H20N4S, contains two independent molecules, the main difference between them being the dihedral angles between the benzene rings [19.99 (17) and 9.72 (17)°]. The molecules both have a trans conformation about the C=N double bond and intramolecular C-H...S and N-H...N hydrogen bonds are observed in both molecules. In the crystal, molecules are linked by weak N-H...S hydrogen bonds with graph-set motif R22(8). In each molecule, all but one of the N atoms and both the S atoms are involved in hydrogen bonding.

Related literature

For details of anion recognition, see: Sessler et al. (2006[Sessler, J. L., Gale, P. A. & Cho, W. S. (2006). In Anion Receptor Chemistry. Cambridge: RSC Publishing.]); Amendola et al. (2006[Amendola, V., Bonizzoni, M., Esteban-Gomez, D., Fabbrizzi, L., Licchelli, M., Sancenn, F. & Taglietti, A. (2006). Coord. Chem. Rev. 250, 1451-1470.]); Fahlbusch et al. (2006[Fahlbusch, T., Frank, M., Schatz, J. & Schmaderer, H. (2006). Eur. J. Org. Chem. pp. 1899-1903.]); Gale & Quesada (2006[Gale, P. A. & Quesada, R. (2006). Coord. Chem. Rev. 250, 3219-3244.]); Perez & Riera (2008[Perez, J. & Riera, L. (2008). Chem. Soc. Rev. 37, 2658-2667.]); Willans et al. (2009[Willans, C. E., Anderson, K. M., Potts, L. C. & Steed, J. W. (2009). Org. Biomol. Chem. 7, 2756-2759.]); Amendola & Fabbrizzi (2009[Amendola, V. & Fabbrizzi, L. (2009). Chem. Commun. pp. 513-531.]); Haridas et al. (2012[Haridas, V., Sahu, S., Praveen Kumar P. P. & Sapala, A. R. (2012). RSC Adv. 2, 12594-12605.]). For applications of thiosemicarbazides, see: Basuli et al. (1998[Basuli, F., Ruf, M., Pierpont, C. G. & Bhattacharya, S. (1998). Inorg. Chem. 37, 6113-6116.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & DeClercq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.]); Kowol et al. (2010[Kowol, C. R., Trondl, R., Arion, V. B., Jakupec, M. A., Lichtscheidl, I. & Keppler, B. K. (2010). Dalton Trans. 39, 704-706.]). For thiosemicarbazones acting as anion acceptors, see: Chikate et al. (2005[Chikate, R. C., Belapure, A. R. & Padhye, S. B. (2005). Polyhedron, 24, 889-899.]); Krisitin (2005[Krisitin, B. J. (2005). Acc. Chem. Res. 38, 671-678.]). For details of the synthesis of the Schiff base ligand, see: Pouralimardan et al. (2007[Pouralimardan, O., Chamayou, A.-C., Janiak, C. & Hosseini-Monfared, H. (2007). Inorg. Chim. Acta, 360, 1599-1608.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20N4S

  • Mr = 312.43

  • Triclinic, [P \overline 1]

  • a = 9.172 (3) Å

  • b = 12.224 (4) Å

  • c = 15.563 (5) Å

  • [alpha] = 86.933 (6)°

  • [beta] = 86.990 (7)°

  • [gamma] = 70.382 (6)°

  • V = 1640.3 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 173 K

  • 0.20 × 0.15 × 0.03 mm

Data collection
  • Brucker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick,2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.961, Tmax = 0.994

  • 7929 measured reflections

  • 5640 independent reflections

  • 3127 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.155

  • S = 0.95

  • 5640 reflections

  • 419 parameters

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4N...N2 0.95 (3) 2.05 (3) 2.587 (3) 114 (3)
C12-H12A...S1 0.93 2.64 3.239 (4) 123
C29-H29A...S2 0.93 2.57 3.257 (4) 131
N7-H7N...S1i 0.86 2.61 3.458 (3) 170
N3-H3N...S2ii 0.86 2.59 3.439 (3) 171
N8-H8N...N6 0.97 (3) 2.01 (3) 2.587 (4) 116 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z-1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2440 ).


Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (No. 21271150) and the Natural Science Foundation of Fujian Province (No. 2010 J01048).

References

Amendola, V., Bonizzoni, M., Esteban-Gomez, D., Fabbrizzi, L., Licchelli, M., Sancenn, F. & Taglietti, A. (2006). Coord. Chem. Rev. 250, 1451-1470.  [ISI] [CrossRef] [ChemPort]
Amendola, V. & Fabbrizzi, L. (2009). Chem. Commun. pp. 513-531.  [CrossRef]
Basuli, F., Ruf, M., Pierpont, C. G. & Bhattacharya, S. (1998). Inorg. Chem. 37, 6113-6116.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Chikate, R. C., Belapure, A. R. & Padhye, S. B. (2005). Polyhedron, 24, 889-899.  [ISI] [CrossRef] [ChemPort]
Fahlbusch, T., Frank, M., Schatz, J. & Schmaderer, H. (2006). Eur. J. Org. Chem. pp. 1899-1903.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gale, P. A. & Quesada, R. (2006). Coord. Chem. Rev. 250, 3219-3244.  [ISI] [CrossRef] [ChemPort]
Haridas, V., Sahu, S., Praveen Kumar P. P. & Sapala, A. R. (2012). RSC Adv. 2, 12594-12605.
Kowol, C. R., Trondl, R., Arion, V. B., Jakupec, M. A., Lichtscheidl, I. & Keppler, B. K. (2010). Dalton Trans. 39, 704-706.  [CSD] [CrossRef] [ChemPort] [PubMed]
Krisitin, B. J. (2005). Acc. Chem. Res. 38, 671-678.  [ISI] [CrossRef] [PubMed]
Pandeya, S. N., Sriram, D., Nath, G. & DeClercq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.  [ISI] [CrossRef] [PubMed] [ChemPort]
Perez, J. & Riera, L. (2008). Chem. Soc. Rev. 37, 2658-2667.  [ISI] [PubMed] [ChemPort]
Pouralimardan, O., Chamayou, A.-C., Janiak, C. & Hosseini-Monfared, H. (2007). Inorg. Chim. Acta, 360, 1599-1608.  [ISI] [CSD] [CrossRef] [ChemPort]
Sessler, J. L., Gale, P. A. & Cho, W. S. (2006). In Anion Receptor Chemistry. Cambridge: RSC Publishing.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Willans, C. E., Anderson, K. M., Potts, L. C. & Steed, J. W. (2009). Org. Biomol. Chem. 7, 2756-2759.  [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o906-o907   [ doi:10.1107/S1600536813012890 ]

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