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Volume 69 
Part 9 
Page o1468  
September 2013  

Received 24 July 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 15.5
Details
Open access

(4-Fluorophenyl)thiourea-1,10-phenanthroline (1/1)

aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
Correspondence e-mail: ctfairus@ukm.my

Refluxing a mixture of 1,10-phenanthroline, (4-fluorophenyl)thiourea and cadmium(II) chloride did not produce the expected mixed-ligand complex but formed a co-crystal of the two ligands, C12H8N2·C7H7FN2S. The asymmetric unit consists of two pairs of the co-crystal molecules. In each (4-fluorophenyl)thiourea molecule, the planes of the N2CS thiourea units are almost perpendicular to the corresponding fluorobenzene rings, subtending angles of 76.53 (7) and 85.25 (7)°. In the crystal, N-H...N and N-H...S hydrogen bonds form inversion dimers from the co-crystal pairs. A weak [pi]-[pi] interaction between the phenanthroline rings [centroid-centroid distance = 3.7430 (15)Å] is also observed.

Related literature

For bond-length data, 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 related structures of other co-crystals formed with 1,10-phenanthroline, see: Ton & Bolte (2005[Ton, Q. C. & Bolte, M. (2005). Acta Cryst. E61, o1406-o1407.]); Wang et al. (2006[Wang, Z.-L., Li, M.-X., Wei, L.-H. & Wang, J.-P. (2006). Acta Cryst. E62, o2508-o2509.]); Shan et al. (2001[Shan, N., Bond, A. D. & Jones, W. (2001). Acta Cryst. E57, o811-o813.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8N2·C7H7FN2S

  • Mr = 350.41

  • Triclinic, [P \overline 1]

  • a = 10.245 (3) Å

  • b = 12.720 (3) Å

  • c = 15.222 (4) Å

  • [alpha] = 69.523 (4)°

  • [beta] = 75.854 (5)°

  • [gamma] = 66.565 (4)°

  • V = 1692.2 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 298 K

  • 0.50 × 0.49 × 0.41 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.902, Tmax = 0.919

  • 20024 measured reflections

  • 6992 independent reflections

  • 5255 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.121

  • S = 1.03

  • 6992 reflections

  • 451 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N5i 0.86 2.28 3.076 (2) 155
N2-H2A...N6i 0.86 2.08 2.870 (2) 152
N2-H2B...S1ii 0.86 2.67 3.4770 (19) 158
N3-H3...N8iii 0.86 2.36 3.186 (2) 161
N4-H4A...N7iii 0.86 2.11 2.889 (2) 150
N4-H4B...S2iv 0.86 2.67 3.485 (2) 157
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, 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, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5347 ).


Acknowledgements

The authors would like to thank Universiti Kebangsaan Malaysia and the Ministry of Science and Technology, Malaysia, for research grants 06-01-02-SF0844 and DIP-2012-11, and the Centre of Research and Instrumentation (CRIM) for research facilities.

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.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Shan, N., Bond, A. D. & Jones, W. (2001). Acta Cryst. E57, o811-o813.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Ton, Q. C. & Bolte, M. (2005). Acta Cryst. E61, o1406-o1407.  [CSD] [CrossRef] [ChemPort] [details]
Wang, Z.-L., Li, M.-X., Wei, L.-H. & Wang, J.-P. (2006). Acta Cryst. E62, o2508-o2509.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1468  [ doi:10.1107/S1600536813023222 ]

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