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Volume 69 
Part 12 
Page o1828  
December 2013  

Received 25 October 2013
Accepted 21 November 2013
Online 27 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.165
Data-to-parameter ratio = 17.9
Details
Open access

N'-[(E)-2-Fluoro­benzyl­idene]benzo­hydrazide

aDepartment of Chemistry, Christ University, Hosur Road, Bangalore 560 029, Karnataka, India,bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
Correspondence e-mail: eesans@yahoo.com

The asymmetric unit of the title compound, C14H11FN2O, contains two independent mol­ecules, both of which adopt the E conformation with respect to the azomethine C=N bond. The mol­ecules are non-planar, with dihedral angles of 26.92 (12) and 11.36 (11)° between the benzene and phenyl rings. In the crystal, mol­ecules are linked through N-H...O=C and N-H...N hydrogen bonds into chains along [101]. C-H...O contacts link these chains into layers parallel to (001). The three-dimensional crystal packing is stabilized by [pi]-[pi] inter­actions, the shortest separation between the centroids of benzene rings being 3.884 (1) Å.

Related literature

For catalytic properties of hydrazones, see: Heravi et al. (2007[Heravi, M. M., Ranjbar, L., Derikvand, F., Oskooie, H. A. & Bamoharram, F. F. (2007). J. Mol. Catal. A Chem. 265, 186-188.]). For their use as inhibitors of enzymes, see: Tamasi et al. (2005[Tamasi, G., Chiasserini, L., Savini, L., Sega, A. & Cini, R. (2005). J. Inorg. Biochem. 99, 1347-1359.]) and for their biological activity, see: Sreeja et al. (2004[Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.]). For the synthesis of related compounds, see: Mangalam & Kurup (2011[Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 76, 22-28.]). For a related structure, see: Nair et al. (2012[Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11FN2O

  • Mr = 242.25

  • Monoclinic, P 21 /n

  • a = 9.7010 (6) Å

  • b = 17.4114 (13) Å

  • c = 15.002 (1) Å

  • [beta] = 104.126 (4)°

  • V = 2457.3 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.977

  • 18766 measured reflections

  • 6111 independent reflections

  • 3320 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.165

  • S = 1.00

  • 5972 reflections

  • 333 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.21 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
N2-H2'...O2i 0.89 (1) 2.09 (2) 2.875 (2) 147 (2)
N2-H2'...N3i 0.89 (1) 2.60 (2) 3.339 (2) 142 (2)
N4-H4'...O1 0.87 (1) 2.03 (1) 2.882 (2) 171 (2)
C7-H7...O2i 0.93 2.53 3.213 (2) 131
C14-H14...O2i 0.93 2.49 3.402 (3) 166
C16-H16...O2ii 0.93 2.55 3.450 (3) 164
C21-H21...O1 0.93 2.44 3.250 (2) 145
C28-H28...O1 0.93 2.40 3.312 (2) 166
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 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: YK2100 ).


Acknowledgements

PBS is thankful to the Center for Research, Christ University, for financial assistance. NA thanks the University Grants Commission (India) for a Junior Research Fellowship. MRPK thanks the University Grants Commission, New Delhi, for a UGC-BSR one-time grant to faculty. The authors thank the Sophisticated Analytical Instruments Facility, Cochin University of S & T, for the diffraction measurements.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Heravi, M. M., Ranjbar, L., Derikvand, F., Oskooie, H. A. & Bamoharram, F. F. (2007). J. Mol. Catal. A Chem. 265, 186-188.  [Web of Science] [CrossRef] [ChemPort]
Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 76, 22-28.
Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Tamasi, G., Chiasserini, L., Savini, L., Sega, A. & Cini, R. (2005). J. Inorg. Biochem. 99, 1347-1359.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1828  [ doi:10.1107/S1600536813031747 ]

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