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Volume 69 
Part 7 
Page o1018  
July 2013  

Received 2 May 2013
Accepted 28 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.170
Data-to-parameter ratio = 12.6
Details
Open access

4,7-Diphenyl-1,10-phenanthroline methanol hemisolvate

aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal,bEnvironmental Engineering Department, University of Valladolid, P-34004 Palencia, Spain, and cChemistry Department, University of Coimbra, P-3004 Coimbra, Portugal
Correspondence e-mail: manuela@pollux.fis.uc.pt

The asymmetric unit of the title compound, C24H16N2·0.5CH3OH, is comprised of two independent bathophenanthroline molecules (systematic name: 4,7-diphenyl-1,10-phenanthroline) and one methanol molecule. The bathophenanthroline molecules are not planar as there is a considerable rotation of all terminal phenyl rings with respect to the central phenanthroline units [dihedral angles in the range 52.21 (12)-62.14 (10)°]. In addition, a non-negligible torsion is apparent in one of the phenanthroline units: the angle between the mean planes of the two pyridine rings is 14.84 (13)°. The methanol solvent molecule is linked to both N atoms of a bathophenanthroline molecule through a bifurcated O-H...(N,N) hydrogen bond.

Related literature

For background on aromatic N-donor lanthanide complexes, see: Martín-Ramos et al. (2013a[Martín-Ramos, P., Coya, C., Alvarez, A. L., Ramos Silva, M., Zaldo, C., Paixão, J. A., Chamorro-Posada, P. & Martín-Gil, J. (2013a). J. Phys. Chem. C, 117, 10020-10030.],b[Martín-Ramos, P., Ramos-Silva, M., Coya, C., Zaldo, C., Alvarez, A. L., Alvarez-García, S., Matos-Beja, A. M. & Martín-Gil, J. (2013b). J. Mater. Chem. C, 1, 2725-2734.]); Reifernberger et al. (2005[Reifernberger, J. G., Ge, P. & Selvin, P. R. (2005). Rev. Fluoresc. 2, 399-431.]). For information on pure bathophenanthroline, see: Ceolin et al. (1979[Ceolin, R., Mariaud, M., Levillain, P. & Rodier, N. (1979). Acta Cryst. B35, 1630-1632.]).

[Scheme 1]

Experimental

Crystal data
  • C24H16N2·0.5CH4O

  • Mr = 348.41

  • Triclinic, [P \overline 1]

  • a = 7.2094 (3) Å

  • b = 14.8067 (6) Å

  • c = 18.1459 (7) Å

  • [alpha] = 109.797 (2)°

  • [beta] = 99.921 (3)°

  • [gamma] = 92.056 (3)°

  • V = 1785.99 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.50 × 0.22 × 0.10 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.865, Tmax = 0.999

  • 36139 measured reflections

  • 6169 independent reflections

  • 3407 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.170

  • S = 0.98

  • 6160 reflections

  • 489 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1i 0.82 2.13 2.873 (3) 151
O1-H1A...N2i 0.82 2.65 3.318 (3) 140
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2098 ).


Acknowledgements

This work was supported by the Fundo Europeu de Desenvolvimento Regional-QREN-COMPETE through projects PEst-C/FIS/UI0036/2011, PTDC/FIS/102284/2008, PTDC/AAC-CLI/098308/2008 and PTDC/AAC-CLI/118092/2010-Fundação para a Ciência e a Tecnologia (FCT).

References

Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ceolin, R., Mariaud, M., Levillain, P. & Rodier, N. (1979). Acta Cryst. B35, 1630-1632.  [CrossRef] [IUCr Journals]
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Martín-Ramos, P., Coya, C., Alvarez, A. L., Ramos Silva, M., Zaldo, C., Paixão, J. A., Chamorro-Posada, P. & Martín-Gil, J. (2013a). J. Phys. Chem. C, 117, 10020-10030.
Martín-Ramos, P., Ramos-Silva, M., Coya, C., Zaldo, C., Alvarez, A. L., Alvarez-García, S., Matos-Beja, A. M. & Martín-Gil, J. (2013b). J. Mater. Chem. C, 1, 2725-2734.
Reifernberger, J. G., Ge, P. & Selvin, P. R. (2005). Rev. Fluoresc. 2, 399-431.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1018  [ doi:10.1107/S1600536813014682 ]

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