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Volume 70 
Part 1 
Page o80  
January 2014  

Received 10 December 2013
Accepted 14 December 2013
Online 21 December 2013

Key indicators
Single-crystal X-ray study
T = 144 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.099
Data-to-parameter ratio = 15.7
Details
Open access

(E)-1,1-Diphenyl-2-(thio­phen-2-yl­methyl­idene)hydrazine

aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla 72570, Puebla, Pue., Mexico, and bFacultad de Química, Universidad Nacional Autónoma de México, 04510, México DF, Mexico
Correspondence e-mail: bmcabreravivas@yahoo.com

The asymmetric unit of the title compound, C17H14N2S, consists of two crystallographically independent mol­ecules with similar conformations. The dihedral angles between the phenyl rings are 89.32 (5) and 82.80 (5)° in the two mol­ecules. In the crystal, mol­ecules are linked by C-H...[pi] inter­actions, forming a three-dimensional network.

Related literature

For biological applications of hydrazine derivatives, see: Vogel et al. (2008[Vogel, S., Kaufmann, D., Pojarová, M., Müller, Ch., Pfaller, T., Kühne, S., Bednarski, P. J. & von Angerer, E. (2008). Bioorg. Med. Chem. 16, 6436-6447.]); Moreira et al. (2012[Moreira, T., Delle, F., Domeneghini, L., Mascarello, A., Stumpf, T. R., Zanetti, C. R., Bardini, D., Célia Regina Monte, C. R., Albino, E. F., Viancelli, A., Totaro, L. A., Yunes, R. A., Nunes, R. J. & Smânia, A. (2012). Bioorg. Med. Chem. Lett. 22, 225-230.]); Vicini et al. (2009[Vicini, P., Incerti, M., Colla, P. & Loddo, R. (2009). Eur. J. Med. Chem. 44, 1801-1807.]); Belkheiri et al. (2010[Belkheiri, N., Bouguerne, B., Bedos-Belval, F., Duran, H., Bernis, C., Salvayre, R., Nègre-Salvayre, A. & Baltas, M. (2010). Eur. J. Med. Chem. 45, 3019-3026.]); Shen et al. (2011[Shen, P., Liu, X., Jiang, Sh., Huang, Y., Yi, L., Zhao, B. & Tan, S. (2011). Org. Electron. 12, 1992-2002.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14N2S

  • Mr = 278.36

  • Triclinic, [P \overline 1]

  • a = 9.8336 (11) Å

  • b = 9.8665 (9) Å

  • c = 16.6357 (8) Å

  • [alpha] = 100.290 (6)°

  • [beta] = 101.696 (7)°

  • [gamma] = 109.129 (9)°

  • V = 1439.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 144 K

  • 0.58 × 0.51 × 0.36 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.916, Tmax = 0.939

  • 10771 measured reflections

  • 5672 independent reflections

  • 4856 reflections with I > 2[sigma](I)

  • Rint = 0.020

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

  • wR(F2) = 0.099

  • S = 1.07

  • 5672 reflections

  • 361 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1A-C6A, C7A-C12A, C1B-C6B and C7B-C12B phenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3A-H3A...Cg5i 0.95 2.76 3.553 (2) 141
C8A-H8A...Cg2ii 0.95 2.97 3.740 (2) 139
C15B-H15B...Cg2iii 0.95 2.60 3.484 (2) 156
C16A-H16A...Cg6iv 0.95 2.72 3.5725 (19) 150
C16B-H16B...Cg3v 0.95 2.80 3.659 (2) 151
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z; (iv) -x+2, -y+1, -z+1; (v) x, y, z-1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, 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: 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.]); 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: IS5326 ).


Acknowledgements

We are grateful for financial support by project Nos. CAVB-NAT13-G, VIEP, BUAP and MELR-NAT13-G. MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Belkheiri, N., Bouguerne, B., Bedos-Belval, F., Duran, H., Bernis, C., Salvayre, R., Nègre-Salvayre, A. & Baltas, M. (2010). Eur. J. Med. Chem. 45, 3019-3026.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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]
Moreira, T., Delle, F., Domeneghini, L., Mascarello, A., Stumpf, T. R., Zanetti, C. R., Bardini, D., Célia Regina Monte, C. R., Albino, E. F., Viancelli, A., Totaro, L. A., Yunes, R. A., Nunes, R. J. & Smânia, A. (2012). Bioorg. Med. Chem. Lett. 22, 225-230.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shen, P., Liu, X., Jiang, Sh., Huang, Y., Yi, L., Zhao, B. & Tan, S. (2011). Org. Electron. 12, 1992-2002.  [Web of Science] [CrossRef] [ChemPort]
Vicini, P., Incerti, M., Colla, P. & Loddo, R. (2009). Eur. J. Med. Chem. 44, 1801-1807.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Vogel, S., Kaufmann, D., Pojarová, M., Müller, Ch., Pfaller, T., Kühne, S., Bednarski, P. J. & von Angerer, E. (2008). Bioorg. Med. Chem. 16, 6436-6447.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2014). E70, o80  [ doi:10.1107/S1600536813033874 ]

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